data_ex535 _publ_contact_author_name 'Thomas M. Klapo\"tke' _publ_contact_author_address ; Department Chemie Ludwig-Maximilians Universit\"at Butenandtstra\&se 5-13 (Haus D) D-81377 M\"unchen Bundesrepublik Deutschland ; _publ_author_name ; Klap\"otke, Thomas M. Stierstorfer, Joerg ; _publ_author_address ; Der Finch Department Chemie Ludwig-Maximilians Universit\"at Butenandtstrasse 5-13 (Haus D) D-81377 M\"unchen Bundesrepublik Deutschland Klap\"otke, Thomas M. Department Chemie Ludwig-Maximilians Universit\"at Butenandtstrasse 5-13 (Haus D) D-81377 M\"unchen Bundesrepublik Deutschland Stierstorfer, Joerg Department Chemie Ludwig-Maximilians Universit\"at Butenandtstrasse 5-13 (Haus D) D-81377 M\"unchen Bundesrepublik Deutschland ; _publ_contact_author_email 'tmk@cup.uni-muenchen.de' _publ_contact_author_fax '+49-89-2180-77491' _publ_contact_author_phone '+49-89-2180-77492' _publ_requested_journal 'Chem. Mater.' _publ_section_title ;Salts of 2-Methyl-5-nitraminotetrazolate - - Secondary Explosives with Low Sensitivities ; _publ_section_abstract ? _publ_section_comment ? _audit_author_name 'Joerg Stierstorfer' _audit_block_code ? _audit_creation_method SHELXL-97 _audit_creation_date ; 'Sun Nov 22 22:01:53 2009' ; _audit_update_record '24.11.2009' _chemical_name_systematic 'guanidinium 2-methyl-5-nitriminotetrazolate' _chemical_compound_source ? _chemical_name_common 'guanidinium 2-methyl-5-nitriminotetrazolate' _chemical_formula_moiety 'C2 H3 N6 O2, C H6 N3' _chemical_formula_sum 'C3 H9 N9 O2' _chemical_formula_weight 203.19 _diffrn_ambient_temperature 200 # in K _diffrn_source_type 'Spellman generator' _diffrn_source_power ? # in kW _diffrn_source_voltage 50 # kV _diffrn_source_current 40 # mA _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'graphite' _diffrn_radiation_collimation 0.5 _diffrn_measurement_device 'CCD camera on \k-goniostat' _diffrn_measurement_device_type 'KappaCCD' _diffrn_measurement_method 'omega-scan' _diffrn_radiation_type 'Mo K\a' _diffrn_detector_area_resol_mean 15.9809 _diffrn_reflns_number 1703 _diffrn_reflns_av_R_equivalents 0.0276 _diffrn_reflns_av_sigmaI/netI 0.0626 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 3 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 4.41 _diffrn_reflns_theta_max 28.29 _diffrn_measured_fraction_theta_max 0.902 _diffrn_reflns_theta_full 28.29 _diffrn_measured_fraction_theta_full 0.902 _reflns_number_total 988 _reflns_number_gt 756 _reflns_threshold_expression >2sigma(I) _diffrn_orient_matrix_UB_11 -0.1779167478 _diffrn_orient_matrix_UB_12 -0.0304929671 _diffrn_orient_matrix_UB_13 0.0059014520 _diffrn_orient_matrix_UB_21 -0.0796110459 _diffrn_orient_matrix_UB_22 0.0712927120 _diffrn_orient_matrix_UB_23 -0.0227166816 _diffrn_orient_matrix_UB_31 -0.0060784882 _diffrn_orient_matrix_UB_32 -0.0396524459 _diffrn_orient_matrix_UB_33 -0.0454470076 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21 1' _symmetry_Int_Tables_number 4 _symmetry_space_group_name_Hall 'P 2yb' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 3.6562(3) _cell_length_b 8.1552(8) _cell_length_c 13.9458(11) _cell_angle_alpha 90.00 _cell_angle_beta 95.919(8) _cell_angle_gamma 90.00 _cell_volume 413.61(6) _cell_formula_units_Z 2 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 782 _cell_measurement_theta_min 4.3957 _cell_measurement_theta_max 28.2449 _cell_special_details ? _exptl_crystal_description rods _exptl_crystal_colour colorless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.632 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 212 _exptl_absorpt_coefficient_mu 0.136 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.89206 _exptl_absorpt_correction_T_max 0.99000 _exptl_absorpt_process_details ;SCALE3 ABSPACK - An Oxford Diffraction program (1.0.4,gui:1.0.3) (C) 2005 Oxford Diffraction Ltd. ; _exptl_special_details ? loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist ? ? ? ? _diffrn_special_details ? _refine_diff_density_max 0.257 _refine_diff_density_min -0.236 _refine_diff_density_rms 0.052 _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET) (compiled Apr 1 2005,17:53:34) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET) (compiled Apr 1 2005,17:53:34) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET) (compiled Apr 1 2005,17:53:34) ; _computing_structure_solution 'SIR-92' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; 'ORTEP (M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid # Plot Program for Crystal Structure Illustrations, Oak Ridge National # Laboratory Report ORNL-6895, 1996). Windows version (L. J. Farrugia, Univ. # Glasgow) used --- SCHAKAL (E. Keller, University of Freiburg (Breisgau), # Germany, 1995)' ; _computing_publication_material ;PLATON (A. L. Spek, Acta Crystallogr, Sect. A, 1990, 46, C34, 1995 version). # --- T.B.Cohen, Pure Appl. Chem. 1996,68,2339-2359 (atomic masses). ; _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -10(10) _refine_ls_number_reflns 988 _refine_ls_number_parameters 151 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0547 _refine_ls_R_factor_gt 0.0371 _refine_ls_wR_factor_ref 0.0767 _refine_ls_wR_factor_gt 0.0726 _refine_ls_goodness_of_fit_ref 0.915 _refine_ls_restrained_S_all 0.914 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O2 O 0.0979(6) 0.8434(3) 0.88368(14) 0.0226(6) Uani 1 1 d . . . O1 O -0.1610(6) 0.8910(3) 0.73710(14) 0.0230(6) Uani 1 1 d . . . N6 N 0.0077(7) 0.7955(3) 0.79661(17) 0.0174(6) Uani 1 1 d . . . N5 N 0.1012(7) 0.6463(4) 0.77666(17) 0.0173(6) Uani 1 1 d . . . N4 N 0.1008(7) 0.4328(3) 0.66799(17) 0.0171(6) Uani 1 1 d . . . N1 N -0.2004(6) 0.6546(3) 0.60814(16) 0.0166(6) Uani 1 1 d . . . N9 N -0.4876(7) 1.3948(4) 0.91254(19) 0.0185(6) Uani 1 1 d . . . C4 C -0.3845(8) 1.2487(4) 0.8835(2) 0.0159(7) Uani 1 1 d . . . N7 N -0.4557(8) 1.2041(4) 0.7927(2) 0.0195(6) Uani 1 1 d . . . N3 N -0.0302(7) 0.3968(3) 0.57855(17) 0.0181(6) Uani 1 1 d . . . N2 N -0.2050(7) 0.5306(4) 0.54480(17) 0.0158(6) Uani 1 1 d . . . C2 C -0.3852(8) 0.5381(5) 0.4463(2) 0.0202(7) Uani 1 1 d . . . H2A H -0.4983 0.6462 0.4347 0.030 Uiso 1 1 calc R . . H2B H -0.5753 0.4532 0.4374 0.030 Uiso 1 1 calc R . . H2C H -0.2027 0.5200 0.4006 0.030 Uiso 1 1 calc R . . N8 N -0.2102(7) 1.1447(4) 0.94726(18) 0.0182(6) Uani 1 1 d . . . C1 C -0.0058(8) 0.5878(4) 0.6848(2) 0.0143(7) Uani 1 1 d . . . H7A H -0.602(9) 1.263(5) 0.751(2) 0.024(9) Uiso 1 1 d . . . H8A H -0.110(7) 1.050(4) 0.918(2) 0.007(7) Uiso 1 1 d . . . H8B H -0.148(8) 1.190(4) 1.005(2) 0.024(10) Uiso 1 1 d . . . H9A H -0.457(8) 1.407(5) 0.976(2) 0.020(9) Uiso 1 1 d . . . H9B H -0.610(9) 1.460(5) 0.871(3) 0.030(10) Uiso 1 1 d . . . H7B H -0.370(10) 1.116(5) 0.770(3) 0.030(11) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O2 0.0355(13) 0.0161(14) 0.0151(11) -0.0018(10) -0.0030(10) 0.0035(11) O1 0.0343(12) 0.0156(12) 0.0174(10) 0.0015(11) -0.0057(9) 0.0106(11) N6 0.0225(14) 0.0152(15) 0.0144(14) -0.0032(12) 0.0011(11) 0.0026(12) N5 0.0223(13) 0.0107(12) 0.0184(12) 0.0000(13) 0.0001(10) 0.0038(13) N4 0.0203(13) 0.0134(15) 0.0173(13) -0.0001(11) 0.0013(11) -0.0002(12) N1 0.0170(12) 0.0130(14) 0.0197(13) -0.0003(13) 0.0016(10) -0.0014(12) N9 0.0259(14) 0.0148(15) 0.0140(13) 0.0010(14) -0.0024(11) 0.0037(13) C4 0.0165(15) 0.0134(18) 0.0179(15) 0.0000(14) 0.0026(12) -0.0024(14) N7 0.0266(15) 0.0159(16) 0.0154(13) -0.0015(13) -0.0007(11) 0.0068(13) N3 0.0231(13) 0.0115(13) 0.0194(12) 0.0003(12) 0.0002(10) -0.0007(12) N2 0.0225(14) 0.0105(13) 0.0146(12) -0.0002(12) 0.0019(10) 0.0012(12) C2 0.0233(16) 0.0191(17) 0.0174(14) 0.0036(15) -0.0012(12) -0.0033(15) N8 0.0233(14) 0.0155(14) 0.0148(13) -0.0017(13) -0.0030(11) 0.0003(14) C1 0.0136(14) 0.0123(16) 0.0171(16) 0.0003(13) 0.0025(13) -0.0020(12) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O2 N6 1.286(3) . ? O1 N6 1.253(3) . ? N6 N5 1.302(4) . ? N5 C1 1.385(4) . ? N4 N3 1.322(3) . ? N4 C1 1.351(4) . ? N1 C1 1.338(4) . ? N1 N2 1.342(4) . ? N9 C4 1.325(4) . ? N9 H9A 0.88(3) . ? N9 H9B 0.87(4) . ? C4 N7 1.318(4) . ? C4 N8 1.341(4) . ? N7 H7A 0.89(3) . ? N7 H7B 0.86(4) . ? N3 N2 1.326(4) . ? N2 C2 1.463(3) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? N8 H8A 0.96(3) . ? N8 H8B 0.89(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 N6 O2 119.8(3) . . ? O1 N6 N5 124.2(2) . . ? O2 N6 N5 116.0(2) . . ? N6 N5 C1 117.6(2) . . ? N3 N4 C1 106.8(3) . . ? C1 N1 N2 100.9(3) . . ? C4 N9 H9A 113(3) . . ? C4 N9 H9B 119(2) . . ? H9A N9 H9B 126(3) . . ? N7 C4 N9 120.5(3) . . ? N7 C4 N8 119.7(3) . . ? N9 C4 N8 119.8(3) . . ? C4 N7 H7A 122(2) . . ? C4 N7 H7B 123(2) . . ? H7A N7 H7B 115(3) . . ? N4 N3 N2 105.5(3) . . ? N3 N2 N1 114.4(2) . . ? N3 N2 C2 121.4(3) . . ? N1 N2 C2 124.1(3) . . ? N2 C2 H2A 109.5 . . ? N2 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? N2 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C4 N8 H8A 113.7(16) . . ? C4 N8 H8B 113(2) . . ? H8A N8 H8B 130(3) . . ? N1 C1 N4 112.4(3) . . ? N1 C1 N5 132.5(3) . . ? N4 C1 N5 115.1(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 N6 N5 C1 -2.6(4) . . . . ? O2 N6 N5 C1 177.2(3) . . . . ? C1 N4 N3 N2 0.8(3) . . . . ? N4 N3 N2 N1 -0.7(3) . . . . ? N4 N3 N2 C2 179.4(3) . . . . ? C1 N1 N2 N3 0.3(3) . . . . ? C1 N1 N2 C2 -179.8(3) . . . . ? N2 N1 C1 N4 0.2(3) . . . . ? N2 N1 C1 N5 -179.0(3) . . . . ? N3 N4 C1 N1 -0.6(3) . . . . ? N3 N4 C1 N5 178.7(2) . . . . ? N6 N5 C1 N1 -1.2(5) . . . . ? N6 N5 C1 N4 179.6(3) . . . . ? loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag ? ? ? ? ? ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N7 H7A N4 0.89(3) 2.04(4) 2.924(4) 170(3) 1_465 N8 H8A O2 0.96(3) 1.93(3) 2.881(4) 169(2) . N8 H8B O2 0.89(4) 1.99(4) 2.855(4) 164(3) 2_557 N9 H9A O2 0.88(3) 2.30(3) 3.074(3) 146(3) 2_557 N9 H9A N8 0.88(3) 2.58(4) 3.106(4) 119(3) 2_457 N9 H9B N5 0.87(4) 2.21(4) 3.077(4) 174(3) 1_465 N7 H7B O1 0.86(4) 2.05(4) 2.907(4) 171(3) . _geom_special_details ? #===END data_ex548 _publ_contact_author_name 'Thomas M. Klapo\"tke' _publ_contact_author_address ; Department Chemie Ludwig-Maximilians Universit\"at Butenandtstra\&se 5-13 (Haus D) D-81377 M\"unchen Bundesrepublik Deutschland ; _publ_author_name ; Klap\"otke, Thomas M. Stierstorfer, Joerg ; _publ_author_address ; Der Finch Department Chemie Ludwig-Maximilians Universit\"at Butenandtstrasse 5-13 (Haus D) D-81377 M\"unchen Bundesrepublik Deutschland Klap\"otke, Thomas M. Department Chemie Ludwig-Maximilians Universit\"at Butenandtstrasse 5-13 (Haus D) D-81377 M\"unchen Bundesrepublik Deutschland Stierstorfer, Joerg Department Chemie Ludwig-Maximilians Universit\"at Butenandtstrasse 5-13 (Haus D) D-81377 M\"unchen Bundesrepublik Deutschland ; _publ_contact_author_email 'tmk@cup.uni-muenchen.de' _publ_contact_author_fax '+49-89-2180-77491' _publ_contact_author_phone '+49-89-2180-77492' _publ_requested_journal 'Inorg. Chem.' _publ_section_title ;Salts of 2-Methyl-5-nitraminotetrazolate - - Secondary Explosives with Low Sensitivities ; _publ_section_abstract ? _publ_section_comment ? _audit_author_name 'Joerg Stierstorfer' _audit_block_code ? _audit_creation_method SHELXL-97 _audit_creation_date ; 'Thu Nov 26 01:54:01 2009' ; _audit_update_record '26.11.09' _chemical_name_systematic '1,3,5-triaminoguanidinium 2-methyl-5-nitriminotetrazolate' _chemical_compound_source ? _chemical_name_common 'triaminoguanidinium 2-methyl-5-nitriminotetrazolate' _chemical_formula_moiety 'C H9 N6, C2 H3 N6 O2' _chemical_formula_sum 'C3 H12 N12 O2' _chemical_formula_weight 248.25 _diffrn_ambient_temperature 173 # in K _diffrn_source_type 'Spellman generator' _diffrn_source_power ? # in kW _diffrn_source_voltage 50 # kV _diffrn_source_current 40 # mA _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'graphite' _diffrn_radiation_collimation 0.5 _diffrn_measurement_device 'CCD camera on \k-goniostat' _diffrn_measurement_device_type 'KappaCCD' _diffrn_measurement_method 'omega-scan' _diffrn_radiation_type 'Mo K\a' _diffrn_detector_area_resol_mean 15.9809 _diffrn_reflns_number 5352 _diffrn_reflns_av_R_equivalents 0.0175 _diffrn_reflns_av_sigmaI/netI 0.0246 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 4.21 _diffrn_reflns_theta_max 25.98 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.98 _diffrn_measured_fraction_theta_full 0.996 _reflns_number_total 2062 _reflns_number_gt 1650 _reflns_threshold_expression >2sigma(I) _diffrn_orient_matrix_UB_11 -0.0016545777 _diffrn_orient_matrix_UB_12 0.0592334685 _diffrn_orient_matrix_UB_13 -0.0449533592 _diffrn_orient_matrix_UB_21 -0.0120742456 _diffrn_orient_matrix_UB_22 0.0691619336 _diffrn_orient_matrix_UB_23 0.0446258595 _diffrn_orient_matrix_UB_31 0.1115711732 _diffrn_orient_matrix_UB_32 0.0391933818 _diffrn_orient_matrix_UB_33 0.0263738734 _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_Int_Tables_number 2 _symmetry_space_group_name_Hall '-P1' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.9170(4) _cell_length_b 7.5831(5) _cell_length_c 11.0147(7) _cell_angle_alpha 97.315(5) _cell_angle_beta 106.030(5) _cell_angle_gamma 104.979(5) _cell_volume 523.99(6) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3275 _cell_measurement_theta_min 4.1997 _cell_measurement_theta_max 32.3500 _cell_special_details ? _exptl_crystal_description rods _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.573 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 260 _exptl_absorpt_coefficient_mu 0.131 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.95867 _exptl_absorpt_correction_T_max 0.99000 _exptl_absorpt_process_details ;SCALE3 ABSPACK - An Oxford Diffraction program (1.0.4,gui:1.0.3) (C) 2005 Oxford Diffraction Ltd. ; _exptl_special_details ? loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist ? ? ? ? _diffrn_special_details ? _refine_diff_density_max 0.166 _refine_diff_density_min -0.226 _refine_diff_density_rms 0.038 _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET) (compiled Apr 1 2005,17:53:34) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET) (compiled Apr 1 2005,17:53:34) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET) (compiled Apr 1 2005,17:53:34) ; _computing_structure_solution 'SIR-92' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; 'ORTEP (M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid # Plot Program for Crystal Structure Illustrations, Oak Ridge National # Laboratory Report ORNL-6895, 1996). Windows version (L. J. Farrugia, Univ. # Glasgow) used --- SCHAKAL (E. Keller, University of Freiburg (Breisgau), # Germany, 1995)' ; _computing_publication_material ;PLATON (A. L. Spek, Acta Crystallogr, Sect. A, 1990, 46, C34, 1995 version). # --- T.B.Cohen, Pure Appl. Chem. 1996,68,2339-2359 (atomic masses). ; _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 2062 _refine_ls_number_parameters 202 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0372 _refine_ls_R_factor_gt 0.0289 _refine_ls_wR_factor_ref 0.0773 _refine_ls_wR_factor_gt 0.0749 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 1.06642(15) 0.33825(12) 0.77523(9) 0.0304(2) Uani 1 1 d . . . O2 O 0.93918(14) 0.57237(12) 0.78519(9) 0.0301(2) Uani 1 1 d . . . N1 N 0.81242(16) 0.02594(14) 0.59446(9) 0.0219(2) Uani 1 1 d . . . N2 N 0.74690(15) -0.10423(14) 0.48593(9) 0.0207(2) Uani 1 1 d . . . N3 N 0.67000(17) -0.04720(15) 0.38053(10) 0.0265(3) Uani 1 1 d . . . N4 N 0.68339(17) 0.12930(15) 0.41824(10) 0.0275(3) Uani 1 1 d . . . N5 N 0.78747(17) 0.34764(14) 0.61253(10) 0.0263(3) Uani 1 1 d . . . N6 N 0.93232(16) 0.41472(14) 0.72447(10) 0.0223(2) Uani 1 1 d . . . C1 C 0.77113(18) 0.17206(17) 0.54876(12) 0.0207(3) Uani 1 1 d . . . C2 C 0.7448(2) -0.29729(18) 0.48498(14) 0.0263(3) Uani 1 1 d . . . N7 N 0.32516(18) 0.20698(16) 0.09507(10) 0.0254(3) Uani 1 1 d . . . N8 N 0.4418(2) 0.32204(17) 0.21870(10) 0.0268(3) Uani 1 1 d . . . N9 N 0.32597(16) 0.09256(14) -0.10920(10) 0.0224(3) Uani 1 1 d . . . N10 N 0.11059(17) -0.01392(16) -0.14055(11) 0.0240(3) Uani 1 1 d . . . N11 N 0.61213(17) 0.32724(16) 0.03083(11) 0.0268(3) Uani 1 1 d . . . N12 N 0.7090(2) 0.3221(2) -0.06587(12) 0.0339(3) Uani 1 1 d . . . C3 C 0.42015(19) 0.20906(16) 0.00482(11) 0.0202(3) Uani 1 1 d . . . H2C H 0.745(2) -0.351(2) 0.4023(16) 0.040(4) Uiso 1 1 d . . . H2A H 0.868(3) -0.300(2) 0.5492(15) 0.038(4) Uiso 1 1 d . . . H2B H 0.622(3) -0.359(2) 0.4983(15) 0.038(4) Uiso 1 1 d . . . H10B H 0.032(3) 0.028(2) -0.2050(16) 0.041(4) Uiso 1 1 d . . . H8A H 0.490(3) 0.255(2) 0.2690(16) 0.039(4) Uiso 1 1 d . . . H11 H 0.679(3) 0.408(2) 0.1087(16) 0.046(5) Uiso 1 1 d . . . H10A H 0.103(2) -0.132(2) -0.1744(14) 0.037(4) Uiso 1 1 d . . . H9 H 0.381(2) 0.113(2) -0.1697(15) 0.035(4) Uiso 1 1 d . . . H7 H 0.204(3) 0.122(2) 0.0765(14) 0.034(4) Uiso 1 1 d . . . H8B H 0.358(3) 0.369(2) 0.2417(15) 0.039(5) Uiso 1 1 d . . . H12A H 0.832(3) 0.309(3) -0.0333(17) 0.057(6) Uiso 1 1 d . . . H12B H 0.730(3) 0.428(3) -0.0905(18) 0.062(6) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0304(5) 0.0257(5) 0.0289(5) 0.0005(4) -0.0022(4) 0.0136(4) O2 0.0329(5) 0.0181(5) 0.0359(6) -0.0019(4) 0.0093(4) 0.0078(4) N1 0.0238(5) 0.0197(5) 0.0183(5) 0.0008(4) 0.0039(4) 0.0045(4) N2 0.0201(5) 0.0211(5) 0.0181(5) 0.0019(4) 0.0049(4) 0.0040(4) N3 0.0269(6) 0.0292(6) 0.0203(6) 0.0049(5) 0.0042(5) 0.0071(5) N4 0.0286(6) 0.0280(6) 0.0227(6) 0.0067(5) 0.0041(5) 0.0071(5) N5 0.0251(6) 0.0211(6) 0.0273(6) 0.0037(5) 0.0003(5) 0.0078(5) N6 0.0219(5) 0.0179(5) 0.0266(6) 0.0047(4) 0.0082(5) 0.0049(4) C1 0.0155(6) 0.0222(6) 0.0222(6) 0.0054(5) 0.0036(5) 0.0045(5) C2 0.0279(7) 0.0199(7) 0.0286(8) 0.0012(6) 0.0092(6) 0.0051(6) N7 0.0246(6) 0.0288(6) 0.0176(6) -0.0003(5) 0.0049(5) 0.0039(5) N8 0.0322(7) 0.0306(6) 0.0155(6) 0.0011(5) 0.0030(5) 0.0127(5) N9 0.0232(6) 0.0233(6) 0.0168(5) 0.0013(4) 0.0048(5) 0.0041(5) N10 0.0233(6) 0.0213(6) 0.0217(6) 0.0030(5) 0.0023(5) 0.0034(5) N11 0.0264(6) 0.0276(6) 0.0202(6) 0.0005(5) 0.0063(5) 0.0017(5) N12 0.0322(7) 0.0394(8) 0.0285(7) 0.0086(6) 0.0131(6) 0.0044(6) C3 0.0247(6) 0.0178(6) 0.0182(6) 0.0052(5) 0.0038(5) 0.0096(5) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 N6 1.2583(13) . ? O2 N6 1.2760(13) . ? N1 N2 1.3333(14) . ? N1 C1 1.3374(15) . ? N2 N3 1.3129(14) . ? N2 C2 1.4590(16) . ? N3 N4 1.3212(15) . ? N4 C1 1.3557(16) . ? N5 N6 1.2952(15) . ? N5 C1 1.3853(15) . ? C2 H2C 0.950(16) . ? C2 H2A 0.954(16) . ? C2 H2B 0.919(17) . ? N7 C3 1.3340(16) . ? N7 N8 1.4118(15) . ? N7 H7 0.865(17) . ? N8 H8A 0.856(18) . ? N8 H8B 0.829(17) . ? N9 C3 1.3229(15) . ? N9 N10 1.4191(15) . ? N9 H9 0.867(16) . ? N10 H10B 0.911(17) . ? N10 H10A 0.910(16) . ? N11 C3 1.3258(16) . ? N11 N12 1.4078(16) . ? N11 H11 0.908(16) . ? N12 H12A 0.86(2) . ? N12 H12B 0.87(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 N1 C1 101.57(10) . . ? N3 N2 N1 114.14(10) . . ? N3 N2 C2 122.70(10) . . ? N1 N2 C2 122.98(10) . . ? N2 N3 N4 106.29(10) . . ? N3 N4 C1 106.25(10) . . ? N6 N5 C1 116.82(10) . . ? O1 N6 O2 118.62(10) . . ? O1 N6 N5 125.06(10) . . ? O2 N6 N5 116.30(10) . . ? N1 C1 N4 111.75(11) . . ? N1 C1 N5 130.88(11) . . ? N4 C1 N5 117.13(11) . . ? N2 C2 H2C 108.1(9) . . ? N2 C2 H2A 109.8(9) . . ? H2C C2 H2A 109.0(12) . . ? N2 C2 H2B 107.0(9) . . ? H2C C2 H2B 109.8(14) . . ? H2A C2 H2B 112.9(13) . . ? C3 N7 N8 117.83(11) . . ? C3 N7 H7 116.6(10) . . ? N8 N7 H7 124.8(10) . . ? N7 N8 H8A 108.7(11) . . ? N7 N8 H8B 105.6(11) . . ? H8A N8 H8B 113.4(16) . . ? C3 N9 N10 118.46(10) . . ? C3 N9 H9 117.3(10) . . ? N10 N9 H9 120.6(10) . . ? N9 N10 H10B 108.1(10) . . ? N9 N10 H10A 105.3(10) . . ? H10B N10 H10A 107.1(14) . . ? C3 N11 N12 117.72(11) . . ? C3 N11 H11 121.2(10) . . ? N12 N11 H11 121.1(10) . . ? N11 N12 H12A 108.6(12) . . ? N11 N12 H12B 110.1(12) . . ? H12A N12 H12B 106.7(18) . . ? N9 C3 N11 119.92(11) . . ? N9 C3 N7 120.62(11) . . ? N11 C3 N7 119.45(11) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 N1 N2 N3 -0.24(13) . . . . ? C1 N1 N2 C2 -175.52(11) . . . . ? N1 N2 N3 N4 0.04(13) . . . . ? C2 N2 N3 N4 175.33(11) . . . . ? N2 N3 N4 C1 0.19(13) . . . . ? C1 N5 N6 O1 4.75(18) . . . . ? C1 N5 N6 O2 -176.65(10) . . . . ? N2 N1 C1 N4 0.35(13) . . . . ? N2 N1 C1 N5 174.48(12) . . . . ? N3 N4 C1 N1 -0.35(14) . . . . ? N3 N4 C1 N5 -175.37(10) . . . . ? N6 N5 C1 N1 30.31(19) . . . . ? N6 N5 C1 N4 -155.82(11) . . . . ? N10 N9 C3 N11 -171.55(11) . . . . ? N10 N9 C3 N7 9.52(17) . . . . ? N12 N11 C3 N9 -0.41(18) . . . . ? N12 N11 C3 N7 178.54(12) . . . . ? N8 N7 C3 N9 174.07(11) . . . . ? N8 N7 C3 N11 -4.87(17) . . . . ? loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag ? ? ? ? ? ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N10 H10B N1 0.911(17) 2.307(18) 3.1760(15) 159.5(14) 1_454 N10 H10B O1 0.911(17) 2.349(17) 2.9970(15) 128.0(13) 1_454 N8 H8A N4 0.856(18) 2.290(18) 3.1323(17) 167.8(15) . N11 H11 O1 0.908(16) 2.194(17) 3.0038(15) 148.2(14) 2_766 N11 H11 O2 0.908(16) 2.529(17) 3.0382(15) 116.0(12) 2_766 N11 H11 N6 0.908(16) 2.679(17) 3.4354(15) 141.4(13) 2_766 N10 H10A O2 0.910(16) 2.156(17) 2.9673(14) 148.0(13) 1_444 N9 H9 N3 0.867(16) 2.219(16) 2.9732(15) 145.3(13) 2_655 N7 H7 N10 0.865(17) 2.447(17) 3.1966(15) 145.3(13) 2 N8 H8B O2 0.829(17) 2.165(17) 2.9368(16) 154.7(15) 2_666 N12 H12A O2 0.86(2) 2.653(19) 3.2139(16) 123.9(14) 2_766 N12 H12B O2 0.87(2) 2.41(2) 3.0827(16) 134.3(16) 1_554 _geom_special_details ? #===END data_ex549 _publ_contact_author_name 'Thomas M. Klapo\"tke' _publ_contact_author_address ; Department Chemie Ludwig-Maximilians Universit\"at Butenandtstra\&se 5-13 (Haus D) D-81377 M\"unchen Bundesrepublik Deutschland ; _publ_author_name 'Klap\"otke, Thomas M.' _publ_author_address ; Der Finch Department Chemie Ludwig-Maximilians Universit\"at Butenandtstrasse 5-13 (Haus D) D-81377 M\"unchen Bundesrepublik Deutschland Klap\"otke, Thomas M. Department Chemie Ludwig-Maximilians Universit\"at Butenandtstrasse 5-13 (Haus D) D-81377 M\"unchen Bundesrepublik Deutschland Stierstorfer, Joerg Department Chemie Ludwig-Maximilians Universit\"at Butenandtstrasse 5-13 (Haus D) D-81377 M\"unchen Bundesrepublik Deutschland ; _publ_contact_author_email 'tmk@cup.uni-muenchen.de' _publ_contact_author_fax '+49-89-2180-77491' _publ_contact_author_phone '+49-89-2180-77492' _publ_requested_journal 'Chem. Mater.' _publ_section_title ;Salts of 2-Methyl-5-nitraminotetrazolate - - Secondary Explosives with Low Sensitivities ; _publ_section_abstract ? _publ_section_comment ? _audit_author_name 'Joerg Stierstorfer' _audit_block_code ? _audit_creation_method SHELXL-97 _audit_creation_date ; 'Thu Nov 26 11:16:26 2009' ; _audit_update_record '26.11.09' _chemical_name_systematic '2-methyl-5-nitraminotetrazole urea' _chemical_compound_source ? _chemical_name_common '2-methyl-5-nitraminotetrazole urea' _chemical_formula_moiety 'C2 H4 N6 O2, C H4 N2 O' _chemical_formula_sum 'C3 H8 N8 O3' _chemical_formula_weight 204.17 _diffrn_ambient_temperature 173 # in K _diffrn_source_type 'Spellman generator' _diffrn_source_power ? # in kW _diffrn_source_voltage 50 # kV _diffrn_source_current 40 # mA _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'graphite' _diffrn_radiation_collimation 0.5 _diffrn_measurement_device 'CCD camera on \k-goniostat' _diffrn_measurement_device_type 'KappaCCD' _diffrn_measurement_method 'omega-scan' _diffrn_radiation_type 'Mo K\a' _diffrn_detector_area_resol_mean 15.9809 _diffrn_reflns_number 3063 _diffrn_reflns_av_R_equivalents 0.0288 _diffrn_reflns_av_sigmaI/netI 0.0569 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 4.18 _diffrn_reflns_theta_max 25.74 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.74 _diffrn_measured_fraction_theta_full 0.995 _reflns_number_total 1611 _reflns_number_gt 1067 _reflns_threshold_expression >2sigma(I) _diffrn_orient_matrix_UB_11 0.0077020323 _diffrn_orient_matrix_UB_12 -0.0603388332 _diffrn_orient_matrix_UB_13 0.0362982582 _diffrn_orient_matrix_UB_21 0.0929378181 _diffrn_orient_matrix_UB_22 0.0147873213 _diffrn_orient_matrix_UB_23 0.0054949818 _diffrn_orient_matrix_UB_31 -0.0123282236 _diffrn_orient_matrix_UB_32 0.0738074880 _diffrn_orient_matrix_UB_33 0.0285851208 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' _symmetry_Int_Tables_number '14' _symmetry_space_group_name_Hall '-P 2yn' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.5867(5) _cell_length_b 7.3684(7) _cell_length_c 15.3282(9) _cell_angle_alpha 90.00 _cell_angle_beta 95.764(6) _cell_angle_gamma 90.00 _cell_volume 852.54(11) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1139 _cell_measurement_theta_min 4.1746 _cell_measurement_theta_max 28.7584 _cell_special_details ? _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.591 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 424 _exptl_absorpt_coefficient_mu 0.138 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.98383 _exptl_absorpt_correction_T_max 0.99000 _exptl_absorpt_process_details ;SCALE3 ABSPACK - An Oxford Diffraction program (1.0.4,gui:1.0.3) (C) 2005 Oxford Diffraction Ltd. ; _exptl_special_details ? loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist ? ? ? ? _diffrn_special_details ? _refine_diff_density_max 0.206 _refine_diff_density_min -0.221 _refine_diff_density_rms 0.050 _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET) (compiled Apr 1 2005,17:53:34) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET) (compiled Apr 1 2005,17:53:34) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET) (compiled Apr 1 2005,17:53:34) ; _computing_structure_solution 'SIR-92' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; 'ORTEP (M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid # Plot Program for Crystal Structure Illustrations, Oak Ridge National # Laboratory Report ORNL-6895, 1996). Windows version (L. J. Farrugia, Univ. # Glasgow) used --- SCHAKAL (E. Keller, University of Freiburg (Breisgau), # Germany, 1995)' ; _computing_publication_material ;PLATON (A. L. Spek, Acta Crystallogr, Sect. A, 1990, 46, C34, 1995 version). # --- T.B.Cohen, Pure Appl. Chem. 1996,68,2339-2359 (atomic masses). ; _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 1611 _refine_ls_number_parameters 159 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0622 _refine_ls_R_factor_gt 0.0375 _refine_ls_wR_factor_ref 0.0856 _refine_ls_wR_factor_gt 0.0799 _refine_ls_goodness_of_fit_ref 0.881 _refine_ls_restrained_S_all 0.881 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.34194(19) 0.8551(2) 0.88415(8) 0.0466(4) Uani 1 1 d . . . O2 O 0.58417(17) 0.7074(2) 0.86686(8) 0.0433(4) Uani 1 1 d . . . N1 N 0.2372(2) 0.8812(2) 1.04440(9) 0.0300(4) Uani 1 1 d . . . N2 N 0.19931(19) 0.9071(2) 1.12669(8) 0.0280(4) Uani 1 1 d . . . N3 N 0.3188(2) 0.8451(2) 1.18651(9) 0.0341(4) Uani 1 1 d . . . N4 N 0.4458(2) 0.7723(2) 1.14397(9) 0.0356(4) Uani 1 1 d . . . N5 N 0.5010(2) 0.7338(2) 0.99833(10) 0.0320(4) Uani 1 1 d . . . N6 N 0.4725(2) 0.7682(2) 0.91198(9) 0.0321(4) Uani 1 1 d . . . C1 C 0.3914(2) 0.7968(3) 1.05872(11) 0.0263(4) Uani 1 1 d . . . C2 C 0.0377(3) 0.9976(4) 1.14741(16) 0.0407(6) Uani 1 1 d . . . O3 O 0.80235(16) 0.5758(2) 1.04252(7) 0.0388(4) Uani 1 1 d . . . N8 N 0.8047(3) 0.5771(3) 1.18963(11) 0.0413(5) Uani 1 1 d . . . C3 C 0.8834(2) 0.5473(3) 1.11673(11) 0.0283(5) Uani 1 1 d . . . N7 N 1.0486(2) 0.4864(2) 1.12364(11) 0.0338(4) Uani 1 1 d . . . H5 H 0.621(3) 0.677(3) 1.0202(13) 0.057(7) Uiso 1 1 d . . . H7A H 1.101(3) 0.460(3) 1.1715(13) 0.042(6) Uiso 1 1 d . . . H7B H 1.096(3) 0.463(3) 1.0731(13) 0.044(6) Uiso 1 1 d . . . H8A H 0.862(3) 0.571(3) 1.2404(16) 0.069(8) Uiso 1 1 d . . . H8B H 0.694(3) 0.635(3) 1.1844(13) 0.054(7) Uiso 1 1 d . . . H2C H -0.054(3) 0.960(3) 1.1050(16) 0.067(8) Uiso 1 1 d . . . H2A H 0.014(3) 0.966(3) 1.2036(19) 0.082(8) Uiso 1 1 d . . . H2B H 0.045(4) 1.119(5) 1.1357(19) 0.112(12) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0493(9) 0.0638(11) 0.0261(7) 0.0080(7) 0.0015(6) 0.0245(9) O2 0.0363(8) 0.0691(11) 0.0258(7) -0.0040(7) 0.0097(6) 0.0094(8) N1 0.0335(9) 0.0359(10) 0.0208(8) -0.0008(7) 0.0031(6) 0.0059(8) N2 0.0316(9) 0.0316(10) 0.0207(8) -0.0013(7) 0.0021(7) 0.0045(7) N3 0.0320(9) 0.0472(11) 0.0228(8) -0.0011(8) 0.0011(7) 0.0031(8) N4 0.0303(9) 0.0543(12) 0.0221(8) 0.0011(8) 0.0031(7) 0.0050(8) N5 0.0285(9) 0.0493(11) 0.0182(8) 0.0024(7) 0.0014(6) 0.0079(8) N6 0.0337(10) 0.0390(11) 0.0233(8) -0.0002(8) 0.0016(7) 0.0019(8) C1 0.0257(10) 0.0325(11) 0.0206(9) 0.0007(8) 0.0014(8) -0.0007(9) C2 0.0418(14) 0.0450(16) 0.0359(13) -0.0029(12) 0.0074(11) 0.0149(12) O3 0.0307(8) 0.0644(10) 0.0202(7) -0.0007(7) -0.0027(5) 0.0144(7) N8 0.0322(10) 0.0711(15) 0.0204(9) -0.0010(9) 0.0020(8) 0.0083(10) C3 0.0259(11) 0.0360(12) 0.0223(9) 0.0001(9) -0.0008(8) -0.0017(9) N7 0.0273(9) 0.0534(12) 0.0197(9) 0.0036(8) -0.0020(7) 0.0045(9) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 N6 1.2203(19) . ? O2 N6 1.2305(18) . ? N1 C1 1.324(2) . ? N1 N2 1.3352(18) . ? N2 N3 1.3054(19) . ? N2 C2 1.458(2) . ? N3 N4 1.330(2) . ? N4 C1 1.342(2) . ? N5 N6 1.344(2) . ? N5 C1 1.385(2) . ? N5 H5 1.03(2) . ? C2 H2C 0.95(3) . ? C2 H2A 0.93(3) . ? C2 H2B 0.92(4) . ? O3 C3 1.255(2) . ? N8 C3 1.337(2) . ? N8 H8A 0.85(2) . ? N8 H8B 0.94(2) . ? C3 N7 1.326(2) . ? N7 H7A 0.82(2) . ? N7 H7B 0.900(19) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 N2 100.42(14) . . ? N3 N2 N1 114.42(14) . . ? N3 N2 C2 123.13(15) . . ? N1 N2 C2 122.45(16) . . ? N2 N3 N4 106.44(13) . . ? N3 N4 C1 104.82(14) . . ? N6 N5 C1 123.18(16) . . ? N6 N5 H5 116.5(11) . . ? C1 N5 H5 119.4(11) . . ? O1 N6 O2 125.11(15) . . ? O1 N6 N5 119.21(15) . . ? O2 N6 N5 115.69(15) . . ? N1 C1 N4 113.89(15) . . ? N1 C1 N5 128.80(16) . . ? N4 C1 N5 117.31(16) . . ? N2 C2 H2C 107.2(14) . . ? N2 C2 H2A 109.5(16) . . ? H2C C2 H2A 112(2) . . ? N2 C2 H2B 109.5(19) . . ? H2C C2 H2B 102(2) . . ? H2A C2 H2B 117(2) . . ? C3 N8 H8A 121.8(15) . . ? C3 N8 H8B 118.3(12) . . ? H8A N8 H8B 117.9(19) . . ? O3 C3 N7 120.15(15) . . ? O3 C3 N8 120.74(18) . . ? N7 C3 N8 119.12(17) . . ? C3 N7 H7A 121.2(13) . . ? C3 N7 H7B 116.6(13) . . ? H7A N7 H7B 121.8(19) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 N1 N2 N3 0.1(2) . . . . ? C1 N1 N2 C2 -180.0(2) . . . . ? N1 N2 N3 N4 -0.1(2) . . . . ? C2 N2 N3 N4 -179.98(19) . . . . ? N2 N3 N4 C1 0.0(2) . . . . ? C1 N5 N6 O1 -1.9(3) . . . . ? C1 N5 N6 O2 177.99(17) . . . . ? N2 N1 C1 N4 -0.1(2) . . . . ? N2 N1 C1 N5 -179.59(19) . . . . ? N3 N4 C1 N1 0.1(2) . . . . ? N3 N4 C1 N5 179.62(16) . . . . ? N6 N5 C1 N1 7.4(3) . . . . ? N6 N5 C1 N4 -172.03(17) . . . . ? loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag ? ? ? ? ? ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N5 H5 O3 1.03(2) 1.57(2) 2.594(2) 172.6(19) . N7 H7A N3 0.82(2) 2.36(2) 3.159(2) 165.3(19) 2_647 N7 H7B O3 0.900(19) 2.03(2) 2.925(2) 177.1(18) 3_767 N8 H8A O1 0.85(2) 2.29(2) 3.008(2) 142(2) 4_676 N8 H8B N4 0.94(2) 2.17(2) 3.097(3) 168.2(17) . _geom_special_details ? #===END data_ex551 _publ_contact_author_name 'Thomas M. Klapo\"tke' _publ_contact_author_address ; Department Chemie Ludwig-Maximilians Universit\"at Butenandtstra\&se 5-13 (Haus D) D-81377 M\"unchen Bundesrepublik Deutschland ; _publ_author_name 'Klap\"otke, Thomas M.' _publ_author_address ; Der Finch Department Chemie Ludwig-Maximilians Universit\"at Butenandtstrasse 5-13 (Haus D) D-81377 M\"unchen Bundesrepublik Deutschland Klap\"otke, Thomas M. Department Chemie Ludwig-Maximilians Universit\"at Butenandtstrasse 5-13 (Haus D) D-81377 M\"unchen Bundesrepublik Deutschland Stierstorfer, Joerg Department Chemie Ludwig-Maximilians Universit\"at Butenandtstrasse 5-13 (Haus D) D-81377 M\"unchen Bundesrepublik Deutschland ; _publ_contact_author_email 'tmk@cup.uni-muenchen.de' _publ_contact_author_fax '+49-89-2180-77491' _publ_contact_author_phone '+49-89-2180-77492' _publ_requested_journal 'Chem. Mater.' _publ_section_title ;Salts of 2-Methyl-5-nitraminotetrazolate - - Secondary Explosives with Low Sensitivities ; _publ_section_abstract ? _publ_section_comment ? _audit_author_name 'Joerg Stierstorfer' _audit_block_code ? _audit_creation_method SHELXL-97 _audit_creation_date ; 'Thu Nov 26 18:09:02 2009' ; _audit_update_record '27.11.2009' _chemical_name_systematic 'aminoguanidinium 2-methyl-5-nitriminotetrazolate' _chemical_compound_source ? _chemical_name_common 'aminoguanidinium 2-methyl-5-nitriminotetrazolate' _chemical_formula_moiety 'C2 H3 N6 O2, C H7 N4' _chemical_formula_sum 'C3 H10 N10 O2' _chemical_formula_weight 218.21 _diffrn_ambient_temperature 173 # in K _diffrn_source_type 'Spellman generator' _diffrn_source_power ? # in kW _diffrn_source_voltage 50 # kV _diffrn_source_current 40 # mA _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'graphite' _diffrn_radiation_collimation 0.5 _diffrn_measurement_device 'CCD camera on \k-goniostat' _diffrn_measurement_device_type 'KappaCCD' _diffrn_measurement_method 'omega-scan' _diffrn_radiation_type 'Mo K\a' _diffrn_detector_area_resol_mean 15.9809 _diffrn_reflns_number 3303 _diffrn_reflns_av_R_equivalents 0.0238 _diffrn_reflns_av_sigmaI/netI 0.0543 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 4.34 _diffrn_reflns_theta_max 25.99 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.994 _reflns_number_total 1768 _reflns_number_gt 1119 _reflns_threshold_expression >2sigma(I) _diffrn_orient_matrix_UB_11 -0.0991905697 _diffrn_orient_matrix_UB_12 0.0016107784 _diffrn_orient_matrix_UB_13 0.0399888484 _diffrn_orient_matrix_UB_21 -0.1409853117 _diffrn_orient_matrix_UB_22 0.0293005756 _diffrn_orient_matrix_UB_23 -0.0282320710 _diffrn_orient_matrix_UB_31 -0.0789860164 _diffrn_orient_matrix_UB_32 -0.0788152025 _diffrn_orient_matrix_UB_33 -0.0114823037 _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_Int_Tables_number 2 _symmetry_space_group_name_Hall '-P1' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 3.7828(4) _cell_length_b 8.5095(8) _cell_length_c 14.1651(14) _cell_angle_alpha 91.281(8) _cell_angle_beta 95.299(8) _cell_angle_gamma 96.743(8) _cell_volume 450.63(8) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1342 _cell_measurement_theta_min 4.3335 _cell_measurement_theta_max 32.3591 _cell_special_details ? _exptl_crystal_description rod _exptl_crystal_colour colorless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.608 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 228 _exptl_absorpt_coefficient_mu 0.134 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.96284 _exptl_absorpt_correction_T_max 0.99000 _exptl_absorpt_process_details ;SCALE3 ABSPACK - An Oxford Diffraction program (1.0.4,gui:1.0.3) (C) 2005 Oxford Diffraction Ltd. ; _exptl_special_details ? loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist ? ? ? ? _diffrn_special_details ? _refine_diff_density_max 0.152 _refine_diff_density_min -0.219 _refine_diff_density_rms 0.039 _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET) (compiled Apr 1 2005,17:53:34) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET) (compiled Apr 1 2005,17:53:34) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET) (compiled Apr 1 2005,17:53:34) ; _computing_structure_solution 'SIR-92' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; 'ORTEP (M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid # Plot Program for Crystal Structure Illustrations, Oak Ridge National # Laboratory Report ORNL-6895, 1996). Windows version (L. J. Farrugia, Univ. # Glasgow) used --- SCHAKAL (E. Keller, University of Freiburg (Breisgau), # Germany, 1995)' ; _computing_publication_material ;PLATON (A. L. Spek, Acta Crystallogr, Sect. A, 1990, 46, C34, 1995 version). # --- T.B.Cohen, Pure Appl. Chem. 1996,68,2339-2359 (atomic masses). ; _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 1768 _refine_ls_number_parameters 176 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0581 _refine_ls_R_factor_gt 0.0320 _refine_ls_wR_factor_ref 0.0710 _refine_ls_wR_factor_gt 0.0668 _refine_ls_goodness_of_fit_ref 0.828 _refine_ls_restrained_S_all 0.828 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group H8B H -0.373(5) 0.724(2) -0.0469(14) 0.042(6) Uiso 1 1 d . . . H7 H -0.201(4) 0.640(2) 0.1039(12) 0.037(5) Uiso 1 1 d . . . H10a H 0.170(5) 0.730(2) 0.2305(13) 0.048(6) Uiso 1 1 d . . . H8A H -0.666(6) 0.707(2) 0.0077(13) 0.043(6) Uiso 1 1 d . . . H10b H 0.236(5) 0.910(2) 0.2519(13) 0.048(6) Uiso 1 1 d . . . H2B H 1.107(5) 0.366(2) 0.5366(11) 0.038(5) Uiso 1 1 d . . . H2C H 0.750(5) 0.330(2) 0.5825(13) 0.054(6) Uiso 1 1 d . . . H2A H 0.991(5) 0.192(2) 0.5681(13) 0.050(6) Uiso 1 1 d . . . H9B H -0.028(5) 1.085(2) 0.1567(14) 0.050(6) Uiso 1 1 d . . . H9A H -0.282(5) 1.0205(19) 0.0708(13) 0.034(5) Uiso 1 1 d . . . O2 O 0.0687(3) 0.43921(12) 0.13126(8) 0.0332(3) Uani 1 1 d . . . N5 N 0.2764(4) 0.27362(14) 0.23238(9) 0.0258(3) Uani 1 1 d . . . N6 N 0.2400(4) 0.41941(14) 0.21121(9) 0.0263(3) Uani 1 1 d . . . N4 N 0.5283(4) 0.09437(14) 0.33102(9) 0.0297(4) Uani 1 1 d . . . O1 O 0.3705(3) 0.53649(12) 0.26301(8) 0.0402(4) Uani 1 1 d . . . N3 N 0.7025(4) 0.09098(15) 0.41574(10) 0.0307(4) Uani 1 1 d . . . N2 N 0.7390(4) 0.23781(15) 0.45020(9) 0.0270(3) Uani 1 1 d . . . N1 N 0.5961(4) 0.34126(15) 0.39246(10) 0.0284(4) Uani 1 1 d . . . C1 C 0.4664(4) 0.24654(17) 0.31784(11) 0.0227(4) Uani 1 1 d . . . C2 C 0.9150(6) 0.2827(3) 0.54400(14) 0.0370(5) Uani 1 1 d . . . N10 N 0.1060(4) 0.83038(17) 0.21997(10) 0.0299(4) Uani 1 1 d . . . N9 N -0.1432(4) 1.00412(16) 0.11934(11) 0.0282(4) Uani 1 1 d . . . N7 N -0.2446(4) 0.73495(16) 0.08650(9) 0.0261(3) Uani 1 1 d . . . N8 N -0.4682(5) 0.76051(17) 0.00474(11) 0.0288(4) Uani 1 1 d . . . C3 C -0.0935(4) 0.85837(17) 0.14224(11) 0.0225(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O2 0.0436(9) 0.0299(7) 0.0250(7) -0.0019(5) -0.0079(6) 0.0094(5) N5 0.0323(9) 0.0156(7) 0.0285(8) -0.0019(6) -0.0021(6) 0.0027(5) N6 0.0315(9) 0.0234(8) 0.0239(8) -0.0015(6) 0.0025(7) 0.0038(6) N4 0.0360(10) 0.0233(8) 0.0285(9) 0.0005(6) -0.0033(7) 0.0030(6) O1 0.0643(10) 0.0176(6) 0.0347(8) -0.0079(5) -0.0134(6) 0.0038(5) N3 0.0369(10) 0.0244(8) 0.0305(9) 0.0004(6) 0.0001(7) 0.0046(6) N2 0.0291(9) 0.0253(8) 0.0260(8) -0.0006(6) 0.0001(7) 0.0031(6) N1 0.0334(9) 0.0232(7) 0.0276(8) -0.0015(6) -0.0019(7) 0.0037(6) C1 0.0226(10) 0.0203(8) 0.0247(9) -0.0013(6) 0.0031(7) -0.0002(6) C2 0.0412(14) 0.0408(12) 0.0273(11) -0.0019(9) -0.0082(9) 0.0072(10) N10 0.0407(11) 0.0170(8) 0.0298(9) -0.0017(6) -0.0062(7) 0.0023(6) N9 0.0362(10) 0.0199(8) 0.0261(9) -0.0011(6) -0.0079(7) 0.0019(6) N7 0.0333(10) 0.0176(8) 0.0260(8) -0.0013(6) -0.0016(6) 0.0014(6) N8 0.0259(10) 0.0310(8) 0.0278(9) -0.0061(6) -0.0021(7) 0.0010(7) C3 0.0225(10) 0.0219(9) 0.0234(10) -0.0006(7) 0.0059(7) 0.0014(6) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O2 N6 1.2765(16) . ? N5 N6 1.3028(17) . ? N5 C1 1.3876(19) . ? N6 O1 1.2488(16) . ? N4 N3 1.3172(18) . ? N4 C1 1.3567(19) . ? N3 N2 1.3184(17) . ? N2 N1 1.3410(17) . ? N2 C2 1.452(2) . ? N1 C1 1.3345(19) . ? C2 H2B 0.970(19) . ? C2 H2C 0.981(19) . ? C2 H2A 0.914(19) . ? N10 C3 1.319(2) . ? N10 H10a 0.924(19) . ? N10 H10b 0.878(19) . ? N9 C3 1.319(2) . ? N9 H9B 0.90(2) . ? N9 H9A 0.851(18) . ? N7 C3 1.3387(19) . ? N7 N8 1.406(2) . ? N7 H7 0.883(17) . ? N8 H8B 0.91(2) . ? N8 H8A 0.83(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N6 N5 C1 118.27(12) . . ? O1 N6 O2 120.08(12) . . ? O1 N6 N5 123.65(14) . . ? O2 N6 N5 116.24(12) . . ? N3 N4 C1 106.73(12) . . ? N4 N3 N2 105.57(12) . . ? N3 N2 N1 114.72(12) . . ? N3 N2 C2 122.40(14) . . ? N1 N2 C2 122.87(13) . . ? C1 N1 N2 100.82(12) . . ? N1 C1 N4 112.16(14) . . ? N1 C1 N5 132.47(14) . . ? N4 C1 N5 115.35(13) . . ? N2 C2 H2B 107.6(10) . . ? N2 C2 H2C 110.0(11) . . ? H2B C2 H2C 105.5(15) . . ? N2 C2 H2A 105.8(11) . . ? H2B C2 H2A 113.9(16) . . ? H2C C2 H2A 113.8(16) . . ? C3 N10 H10a 120.4(11) . . ? C3 N10 H10b 119.4(12) . . ? H10a N10 H10b 117.1(17) . . ? C3 N9 H9B 118.5(12) . . ? C3 N9 H9A 120.4(11) . . ? H9B N9 H9A 121.2(16) . . ? C3 N7 N8 119.74(14) . . ? C3 N7 H7 117.5(11) . . ? N8 N7 H7 122.7(11) . . ? N7 N8 H8B 108.9(11) . . ? N7 N8 H8A 108.5(13) . . ? H8B N8 H8A 107.6(17) . . ? N10 C3 N9 121.16(15) . . ? N10 C3 N7 118.38(14) . . ? N9 C3 N7 120.46(16) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 N5 N6 O1 1.0(2) . . . . ? C1 N5 N6 O2 178.84(15) . . . . ? C1 N4 N3 N2 0.06(18) . . . . ? N4 N3 N2 N1 0.11(19) . . . . ? N4 N3 N2 C2 179.11(16) . . . . ? N3 N2 N1 C1 -0.22(18) . . . . ? C2 N2 N1 C1 -179.22(17) . . . . ? N2 N1 C1 N4 0.25(18) . . . . ? N2 N1 C1 N5 178.34(18) . . . . ? N3 N4 C1 N1 -0.20(19) . . . . ? N3 N4 C1 N5 -178.65(15) . . . . ? N6 N5 C1 N1 8.9(3) . . . . ? N6 N5 C1 N4 -173.08(14) . . . . ? N8 N7 C3 N10 177.93(16) . . . . ? N8 N7 C3 N9 -2.3(2) . . . . ? loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag ? ? ? ? ? ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N7 H7 O2 0.883(17) 2.113(18) 2.9619(18) 161.0(15) . N10 H10a O1 0.924(19) 1.94(2) 2.8584(18) 171.1(16) . N10 H10a N6 0.924(19) 2.70(2) 3.5932(19) 163.0(14) . N8 H8A O2 0.83(2) 2.577(18) 3.1461(19) 126.7(15) 2_465 N10 H10b N4 0.878(19) 2.057(19) 2.934(2) 177.7(18) 1_565 N9 H9B N5 0.90(2) 2.07(2) 2.9756(19) 174.0(18) 1_565 N9 H9A N8 0.851(18) 2.413(17) 3.104(2) 138.7(14) 2_475 _geom_special_details ? #===END data_ex569 _publ_contact_author_name 'Thomas M. Klapo\"tke' _publ_contact_author_address ; Department Chemie Ludwig-Maximilians Universit\"at Butenandtstra\&se 5-13 (Haus D) D-81377 M\"unchen Bundesrepublik Deutschland ; _publ_author_name 'Klap\"otke, Thomas M.' _publ_author_address ; Fischer, Niko Department Chemie Ludwig-Maximilians Universit\"at Butenandtstrasse 5-13 (Haus D) D-81377 M\"unchen Bundesrepublik Deutschland Klap\"otke, Thomas M. Department Chemie Ludwig-Maximilians Universit\"at Butenandtstrasse 5-13 (Haus D) D-81377 M\"unchen Bundesrepublik Deutschland Stierstorfer, Joerg Department Chemie Ludwig-Maximilians Universit\"at Butenandtstrasse 5-13 (Haus D) D-81377 M\"unchen Bundesrepublik Deutschland ; _publ_contact_author_email 'tmk@cup.uni-muenchen.de' _publ_contact_author_fax '+49-89-2180-77491' _publ_contact_author_phone '+49-89-2180-77492' _publ_requested_journal 'Chem. Mater.' _publ_section_title ;Salts of 2-Methyl-5-nitraminotetrazolate - Secondary Explosives with Low Sensitivities ; _publ_section_abstract ? _publ_section_comment ? _audit_author_name 'Joerg Stierstorfer' _audit_block_code ? _audit_creation_method SHELXL-97 _audit_creation_date ; 'Wed Dec 09 18:31:26 2009' ; _audit_update_record '10.12.2009' _chemical_name_systematic 'diaminoguanidinium 2-methyl-5-nitriminotetrazolate' _chemical_compound_source ? _chemical_name_common 'diaminoguanidinium 2-methyl-5-nitriminotetrazolate' _chemical_formula_moiety 'C H8 N5, C2 H3 N6 O2' _chemical_formula_sum 'C3 H11 N11 O2' _chemical_formula_weight 234.24 _diffrn_ambient_temperature 173 # in K _diffrn_source_type 'Spellman generator' _diffrn_source_power ? # in kW _diffrn_source_voltage 50 # kV _diffrn_source_current 40 # mA _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'graphite' _diffrn_radiation_collimation 0.5 _diffrn_measurement_device 'CCD camera on \k-goniostat' _diffrn_measurement_device_type 'KappaCCD' _diffrn_measurement_method 'omega-scan' _diffrn_radiation_type 'Mo K\a' _diffrn_detector_area_resol_mean 15.9809 _diffrn_reflns_number 5007 _diffrn_reflns_av_R_equivalents 0.0250 _diffrn_reflns_av_sigmaI/netI 0.0378 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 4.28 _diffrn_reflns_theta_max 26.00 _diffrn_measured_fraction_theta_max 0.497 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.497 _reflns_number_total 1948 _reflns_number_gt 1377 _reflns_threshold_expression >2sigma(I) _diffrn_orient_matrix_UB_11 0.0029752143 _diffrn_orient_matrix_UB_12 -0.0677746880 _diffrn_orient_matrix_UB_13 0.0304942365 _diffrn_orient_matrix_UB_21 -0.0290503619 _diffrn_orient_matrix_UB_22 -0.0415535192 _diffrn_orient_matrix_UB_23 -0.0401585558 _diffrn_orient_matrix_UB_31 0.0326868971 _diffrn_orient_matrix_UB_32 -0.0308293581 _diffrn_orient_matrix_UB_33 -0.0128175990 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C2/c' _symmetry_Int_Tables_number 15 _symmetry_space_group_name_Hall ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 17.4021(14) _cell_length_b 8.3403(7) _cell_length_c 14.7111(13) _cell_angle_alpha 90.00 _cell_angle_beta 111.581(9) _cell_angle_gamma 90.00 _cell_volume 1985.5(3) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2200 _cell_measurement_theta_min 4.2385 _cell_measurement_theta_max 33.4107 _cell_special_details ? _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 0.780 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 488 _exptl_absorpt_coefficient_mu 0.065 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.97953 _exptl_absorpt_correction_T_max 0.99000 _exptl_absorpt_process_details ;SCALE3 ABSPACK - An Oxford Diffraction program (1.0.4,gui:1.0.3) (C) 2005 Oxford Diffraction Ltd. ; _exptl_special_details ? loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist ? ? ? ? _diffrn_special_details ? _refine_diff_density_max 0.078 _refine_diff_density_min -0.122 _refine_diff_density_rms 0.025 _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET) (compiled Apr 1 2005,17:53:34) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET) (compiled Apr 1 2005,17:53:34) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET) (compiled Apr 1 2005,17:53:34) ; _computing_structure_solution 'SIR-92' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; 'ORTEP (M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid # Plot Program for Crystal Structure Illustrations, Oak Ridge National # Laboratory Report ORNL-6895, 1996). Windows version (L. J. Farrugia, Univ. # Glasgow) used --- SCHAKAL (E. Keller, University of Freiburg (Breisgau), # Germany, 1995)' ; _computing_publication_material ;PLATON (A. L. Spek, Acta Crystallogr, Sect. A, 1990, 46, C34, 1995 version). # --- T.B.Cohen, Pure Appl. Chem. 1996,68,2339-2359 (atomic masses). ; _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 1948 _refine_ls_number_parameters 189 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0495 _refine_ls_R_factor_gt 0.0328 _refine_ls_wR_factor_ref 0.0759 _refine_ls_wR_factor_gt 0.0722 _refine_ls_goodness_of_fit_ref 0.902 _refine_ls_restrained_S_all 0.902 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.17165(6) 0.14039(12) 0.16981(7) 0.0293(3) Uani 1 1 d . . . O2 O 0.04215(6) 0.13513(14) 0.07317(8) 0.0404(3) Uani 1 1 d . . . N7 N 0.14276(8) 0.54681(15) 0.22681(9) 0.0251(3) Uani 1 1 d . . . N8 N 0.13325(8) 0.41586(16) 0.28286(10) 0.0277(3) Uani 1 1 d . . . N5 N 0.12296(7) 0.30299(14) 0.03706(9) 0.0260(3) Uani 1 1 d . . . N11 N 0.00479(8) 0.52852(19) 0.12942(10) 0.0320(3) Uani 1 1 d . . . N10 N 0.16470(8) 0.78884(19) 0.12246(11) 0.0314(3) Uani 1 1 d . . . N9 N 0.08554(8) 0.72261(16) 0.10026(10) 0.0309(3) Uani 1 1 d . . . N6 N 0.11380(7) 0.19202(14) 0.09524(9) 0.0262(3) Uani 1 1 d . . . N1 N 0.27278(7) 0.33863(15) 0.13102(9) 0.0277(3) Uani 1 1 d . . . N4 N 0.20507(7) 0.49317(16) 0.00244(9) 0.0311(3) Uani 1 1 d . . . N2 N 0.32080(7) 0.44759(16) 0.11184(9) 0.0288(3) Uani 1 1 d . . . N3 N 0.28278(7) 0.54025(16) 0.03673(9) 0.0339(3) Uani 1 1 d . . . C3 C 0.07760(8) 0.59855(17) 0.15233(10) 0.0228(3) Uani 1 1 d . . . C1 C 0.20007(8) 0.37048(17) 0.06071(10) 0.0222(3) Uani 1 1 d . . . C2 C 0.40869(10) 0.4607(3) 0.16937(15) 0.0398(5) Uani 1 1 d . . . H8B H 0.1509(10) 0.448(2) 0.3484(14) 0.046(5) Uiso 1 1 d . . . H8A H 0.1695(10) 0.340(2) 0.2795(11) 0.040(5) Uiso 1 1 d . . . H7 H 0.1858(11) 0.602(2) 0.2439(12) 0.036(5) Uiso 1 1 d . . . H9 H 0.0442(10) 0.7579(19) 0.0510(12) 0.036(5) Uiso 1 1 d . . . H11A H 0.0012(10) 0.448(2) 0.1637(13) 0.039(5) Uiso 1 1 d . . . H11B H -0.0374(11) 0.5686(19) 0.0802(14) 0.044(5) Uiso 1 1 d . . . H2A H 0.4312(11) 0.357(2) 0.1694(13) 0.056(6) Uiso 1 1 d . . . H2B H 0.4148(11) 0.497(2) 0.2314(15) 0.057(6) Uiso 1 1 d . . . H2C H 0.4342(12) 0.526(2) 0.1391(14) 0.056(6) Uiso 1 1 d . . . H10A H 0.1760(10) 0.785(2) 0.0670(14) 0.045(5) Uiso 1 1 d . . . H10B H 0.1620(10) 0.888(2) 0.1404(12) 0.044(6) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0270(5) 0.0310(6) 0.0232(6) 0.0048(5) 0.0012(4) 0.0004(5) O2 0.0257(6) 0.0436(7) 0.0420(7) 0.0061(6) 0.0006(5) -0.0130(5) N7 0.0214(7) 0.0263(7) 0.0229(7) 0.0002(5) 0.0026(5) -0.0029(6) N8 0.0303(7) 0.0280(8) 0.0219(7) 0.0025(6) 0.0063(6) 0.0025(6) N5 0.0232(6) 0.0294(7) 0.0209(7) 0.0031(5) 0.0030(5) -0.0004(5) N11 0.0202(7) 0.0424(9) 0.0278(8) 0.0091(7) 0.0023(6) -0.0027(6) N10 0.0309(7) 0.0311(9) 0.0320(8) -0.0014(6) 0.0112(6) -0.0064(6) N9 0.0225(7) 0.0346(8) 0.0298(8) 0.0082(6) 0.0028(6) -0.0003(6) N6 0.0238(6) 0.0272(7) 0.0233(7) -0.0029(5) 0.0036(5) -0.0016(5) N1 0.0212(6) 0.0351(8) 0.0251(7) 0.0053(6) 0.0064(5) 0.0007(6) N4 0.0261(7) 0.0389(8) 0.0258(7) 0.0076(6) 0.0068(5) -0.0005(6) N2 0.0216(6) 0.0391(8) 0.0252(7) 0.0037(6) 0.0079(5) -0.0006(5) N3 0.0298(7) 0.0430(9) 0.0290(7) 0.0083(6) 0.0110(6) 0.0006(6) C3 0.0226(8) 0.0255(8) 0.0202(7) -0.0036(6) 0.0075(6) 0.0020(6) C1 0.0216(7) 0.0269(8) 0.0167(7) -0.0010(6) 0.0055(5) 0.0036(6) C2 0.0215(8) 0.0566(14) 0.0390(12) 0.0003(10) 0.0087(7) -0.0041(8) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 N6 1.2609(15) . ? O2 N6 1.2598(15) . ? N7 C3 1.3262(17) . ? N7 N8 1.4143(17) . ? N7 H7 0.837(18) . ? N8 H8B 0.937(19) . ? N8 H8A 0.911(18) . ? N5 N6 1.3096(16) . ? N5 C1 1.3767(17) . ? N11 C3 1.3213(18) . ? N11 H11A 0.856(18) . ? N11 H11B 0.886(19) . ? N10 N9 1.4067(18) . ? N10 H10A 0.907(18) . ? N10 H10B 0.87(2) . ? N9 C3 1.3245(19) . ? N9 H9 0.863(17) . ? N1 N2 1.3333(16) . ? N1 C1 1.3336(17) . ? N4 N3 1.3174(16) . ? N4 C1 1.3580(18) . ? N2 N3 1.3108(16) . ? N2 C2 1.4543(19) . ? C2 H2A 0.95(2) . ? C2 H2B 0.93(2) . ? C2 H2C 0.92(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 N7 N8 119.02(12) . . ? C3 N7 H7 117.9(11) . . ? N8 N7 H7 122.4(11) . . ? N7 N8 H8B 108.4(11) . . ? N7 N8 H8A 106.0(10) . . ? H8B N8 H8A 106.5(14) . . ? N6 N5 C1 117.74(11) . . ? C3 N11 H11A 117.8(11) . . ? C3 N11 H11B 118.1(11) . . ? H11A N11 H11B 124.1(16) . . ? N9 N10 H10A 107.2(11) . . ? N9 N10 H10B 106.5(11) . . ? H10A N10 H10B 110.9(16) . . ? C3 N9 N10 118.30(13) . . ? C3 N9 H9 121.3(11) . . ? N10 N9 H9 120.2(11) . . ? O2 N6 O1 119.56(12) . . ? O2 N6 N5 116.39(11) . . ? O1 N6 N5 124.04(11) . . ? N2 N1 C1 100.94(11) . . ? N3 N4 C1 106.14(11) . . ? N3 N2 N1 114.77(11) . . ? N3 N2 C2 122.87(13) . . ? N1 N2 C2 122.35(13) . . ? N2 N3 N4 106.01(12) . . ? N11 C3 N9 119.48(13) . . ? N11 C3 N7 121.01(14) . . ? N9 C3 N7 119.51(13) . . ? N1 C1 N4 112.14(12) . . ? N1 C1 N5 132.30(13) . . ? N4 C1 N5 115.56(11) . . ? N2 C2 H2A 106.0(11) . . ? N2 C2 H2B 108.2(11) . . ? H2A C2 H2B 113.3(16) . . ? N2 C2 H2C 110.9(12) . . ? H2A C2 H2C 105.7(16) . . ? H2B C2 H2C 112.5(16) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 N5 N6 O2 178.32(12) . . . . ? C1 N5 N6 O1 -2.0(2) . . . . ? C1 N1 N2 N3 0.01(16) . . . . ? C1 N1 N2 C2 -179.31(15) . . . . ? N1 N2 N3 N4 -0.05(17) . . . . ? C2 N2 N3 N4 179.26(15) . . . . ? C1 N4 N3 N2 0.06(16) . . . . ? N10 N9 C3 N11 -176.24(15) . . . . ? N10 N9 C3 N7 3.9(2) . . . . ? N8 N7 C3 N11 -0.8(2) . . . . ? N8 N7 C3 N9 179.00(13) . . . . ? N2 N1 C1 N4 0.03(15) . . . . ? N2 N1 C1 N5 179.88(15) . . . . ? N3 N4 C1 N1 -0.06(16) . . . . ? N3 N4 C1 N5 -179.93(12) . . . . ? N6 N5 C1 N1 4.9(2) . . . . ? N6 N5 C1 N4 -175.24(12) . . . . ? loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag ? ? ? ? ? ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N8 H8B N4 0.937(19) 2.17(2) 3.0988(19) 173.2(15) 4_566 N9 H9 O2 0.863(17) 2.091(18) 2.9469(18) 171.0(15) 3_565 N8 H8A O1 0.911(18) 2.325(17) 3.0510(18) 136.5(14) . N10 H10B O1 0.87(2) 2.15(2) 3.006(2) 168.6(16) 1_565 N10 H10B N6 0.87(2) 2.68(2) 3.463(2) 150.1(14) 1_565 N11 H11B N5 0.886(19) 2.109(19) 2.9850(19) 169.7(15) 3_565 _geom_special_details ? #===END data_fx160 _publ_contact_author_name 'Thomas M. Klapo\"tke' _publ_contact_author_address ; Department Chemie Ludwig-Maximilians Universit\"at Butenandtstra\&se 5-13 (Haus D) D-81377 M\"unchen Bundesrepublik Deutschland ; _publ_author_name 'Klap\"otke, Thomas M.' _publ_author_address ; Fischer, Niko Department Chemie Ludwig-Maximilians Univers Butenandtstrasse 5-13 (Hau D-81377 M\"unchen Bundesrepublik Deutschland Klap\"otke, Thomas M. Department Chemie Ludwig-Maximilians Universit\"at Butenandtstrasse 5-13 (Haus D) D-81377 M\"unchen Bundesrepublik Deutschland Stierstorfer, Joerg Department Chemie Ludwig-Maximilians Universit\"at Butenandtstrasse 5-13 (Haus D) D-81377 M\"unchen Bundesrepublik Deutschland ; _publ_contact_author_email 'tmk@cup.uni-muenchen.de' _publ_contact_author_fax '+49-89-2180-77491' _publ_contact_author_phone '+49-89-2180-77492' _publ_requested_journal 'Chem. Mater.' _publ_section_title ;Salts of 2-Methyl-5-nitraminotetrazolate - Secondary Explosives with Low Sensitivities ; _publ_section_abstract ? _publ_section_comment ? _audit_author_name 'Joerg Stierstorfer' _audit_block_code ? _audit_creation_method SHELXL-97 _audit_creation_date ; 'Thu Apr 29 13:35:34 2010' ; _audit_update_record ? _chemical_name_systematic 'diaminouronium 2-methyl-5-nitriminotetrazolate' _chemical_compound_source ? _chemical_name_common 'diaminouronium 2-methyl-5-nitriminotetrazolate' _chemical_formula_moiety 'C2 H3 N6 O2, C H7 N4 O' _chemical_formula_sum 'C3 H10 N10 O3' _chemical_formula_weight 234.21 _diffrn_ambient_temperature 173 # in K _diffrn_source_type 'Spellman generator' _diffrn_source_power ? # in kW _diffrn_source_voltage 50 # kV _diffrn_source_current 40 # mA _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'graphite' _diffrn_radiation_collimation 0.5 _diffrn_measurement_device 'CCD camera on \k-goniostat' _diffrn_measurement_device_type 'KappaCCD' _diffrn_measurement_method 'omega-scan' _diffrn_radiation_type 'Mo K\a' _diffrn_detector_area_resol_mean 15.9809 _diffrn_reflns_number 3466 _diffrn_reflns_av_R_equivalents 0.0168 _diffrn_reflns_av_sigmaI/netI 0.0333 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 34 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 4.49 _diffrn_reflns_theta_max 27.00 _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.977 _reflns_number_total 1926 _reflns_number_gt 1496 _reflns_threshold_expression >2sigma(I) _diffrn_orient_matrix_UB_11 -0.1664785660 _diffrn_orient_matrix_UB_12 0.0087743111 _diffrn_orient_matrix_UB_13 -0.0148198393 _diffrn_orient_matrix_UB_21 -0.0605557051 _diffrn_orient_matrix_UB_22 -0.0231639843 _diffrn_orient_matrix_UB_23 -0.0300827901 _diffrn_orient_matrix_UB_31 -0.0087444894 _diffrn_orient_matrix_UB_32 -0.0068988927 _diffrn_orient_matrix_UB_33 0.0823837753 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_Int_Tables_number 14 _symmetry_space_group_name_Hall '-P 2ybc' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 4.1035(3) _cell_length_b 27.597(3) _cell_length_c 8.1745(5) _cell_angle_alpha 90.00 _cell_angle_beta 103.105(7) _cell_angle_gamma 90.00 _cell_volume 901.60(13) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1785 _cell_measurement_theta_min 4.4818 _cell_measurement_theta_max 28.4435 _cell_special_details ? _exptl_crystal_description rods _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.725 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 488 _exptl_absorpt_coefficient_mu 0.148 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.98189 _exptl_absorpt_correction_T_max 0.99000 _exptl_absorpt_process_details ;SCALE3 ABSPACK - An Oxford Diffraction program (1.0.4,gui:1.0.3) (C) 2005 Oxford Diffraction Ltd. ; _exptl_special_details ? loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist ? ? ? ? _diffrn_special_details ? _refine_diff_density_max 1.035 _refine_diff_density_min -0.836 _refine_diff_density_rms 0.082 _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET) (compiled Apr 1 2005,17:53:34) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET) (compiled Apr 1 2005,17:53:34) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET) (compiled Apr 1 2005,17:53:34) ; _computing_structure_solution 'SIR-92' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; 'ORTEP (M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid # Plot Program for Crystal Structure Illustrations, Oak Ridge National # Laboratory Report ORNL-6895, 1996). Windows version (L. J. Farrugia, Univ. # Glasgow) used --- SCHAKAL (E. Keller, University of Freiburg (Breisgau), # Germany, 1995)' ; _computing_publication_material ;PLATON (A. L. Spek, Acta Crystallogr, Sect. A, 1990, 46, C34, 1995 version). # --- T.B.Cohen, Pure Appl. Chem. 1996,68,2339-2359 (atomic masses). ; _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 1926 _refine_ls_number_parameters 185 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0693 _refine_ls_R_factor_gt 0.0539 _refine_ls_wR_factor_ref 0.1419 _refine_ls_wR_factor_gt 0.1352 _refine_ls_goodness_of_fit_ref 1.108 _refine_ls_restrained_S_all 1.108 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O -0.0791(5) 0.10288(8) 0.4232(2) 0.0303(5) Uani 1 1 d . . . N9 N 0.2373(6) 0.32061(9) 0.6962(3) 0.0261(6) Uani 1 1 d . . . O2 O -0.3562(5) 0.16135(7) 0.5107(3) 0.0280(5) Uani 1 1 d . . . N4 N 0.4353(6) 0.08767(8) 0.9007(3) 0.0206(5) Uani 1 1 d . . . N5 N 0.0260(6) 0.12455(8) 0.6973(3) 0.0197(5) Uani 1 1 d . . . N8 N 0.5466(6) 0.20246(9) 0.8082(3) 0.0240(6) Uani 1 1 d . . . N10 N -0.0211(6) 0.34479(9) 0.5846(3) 0.0229(5) Uani 1 1 d . . . N2 N 0.5514(6) 0.02595(8) 0.7733(3) 0.0193(5) Uani 1 1 d . . . C1 C 0.2529(6) 0.08690(9) 0.7408(3) 0.0169(5) Uani 1 1 d . . . N3 N 0.6238(6) 0.04830(8) 0.9188(3) 0.0212(5) Uani 1 1 d . . . N6 N -0.1308(6) 0.12808(8) 0.5400(3) 0.0207(5) Uani 1 1 d . . . N1 N 0.3204(6) 0.04826(8) 0.6560(3) 0.0207(5) Uani 1 1 d . . . N7 N 0.5015(9) 0.25190(10) 0.8078(4) 0.0526(11) Uani 1 1 d . . . C3 C 0.2578(6) 0.27234(9) 0.6894(3) 0.0170(5) Uani 1 1 d . . . O3 O 0.0841(9) 0.24730(9) 0.5879(4) 0.0923(15) Uani 1 1 d . . . C2 C 0.6984(8) -0.02029(10) 0.7432(4) 0.0240(6) Uani 1 1 d . . . H2B H 0.882(9) -0.0264(13) 0.838(4) 0.035(9) Uiso 1 1 d . . . H9 H 0.352(9) 0.3345(14) 0.786(5) 0.041(10) Uiso 1 1 d . . . H2A H 0.788(8) -0.0180(12) 0.641(4) 0.032(9) Uiso 1 1 d . . . H7 H 0.620(9) 0.2668(14) 0.882(5) 0.040(11) Uiso 1 1 d . . . H10B H 0.078(8) 0.3667(13) 0.530(4) 0.029(9) Uiso 1 1 d . . . H2C H 0.519(10) -0.0443(14) 0.722(5) 0.046(11) Uiso 1 1 d . . . H10A H -0.145(9) 0.3594(13) 0.643(5) 0.035(10) Uiso 1 1 d . . . H8A H 0.700(10) 0.1925(14) 0.908(5) 0.049(11) Uiso 1 1 d . . . H8C H 0.352(12) 0.1885(16) 0.801(5) 0.061(13) Uiso 1 1 d . . . H8B H 0.618(13) 0.1933(19) 0.706(7) 0.089(17) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0402(12) 0.0268(11) 0.0200(10) -0.0024(8) -0.0014(9) 0.0011(9) N9 0.0282(13) 0.0187(12) 0.0234(13) -0.0012(10) -0.0106(10) 0.0001(10) O2 0.0240(10) 0.0222(10) 0.0336(11) 0.0084(9) -0.0025(8) 0.0053(8) N4 0.0227(12) 0.0188(11) 0.0185(11) -0.0005(9) 0.0008(9) 0.0004(9) N5 0.0218(11) 0.0185(11) 0.0177(11) 0.0030(9) 0.0020(9) 0.0032(9) N8 0.0203(12) 0.0181(12) 0.0286(14) 0.0028(10) -0.0049(10) 0.0000(10) N10 0.0262(12) 0.0190(12) 0.0202(12) 0.0022(10) -0.0016(10) 0.0025(10) N2 0.0222(11) 0.0182(11) 0.0157(11) -0.0002(9) 0.0004(9) 0.0017(9) C1 0.0173(12) 0.0159(12) 0.0170(12) 0.0007(10) 0.0027(9) -0.0020(10) N3 0.0235(11) 0.0200(11) 0.0184(11) -0.0013(9) 0.0009(9) 0.0025(9) N6 0.0196(11) 0.0176(11) 0.0224(12) 0.0041(9) -0.0005(9) -0.0025(9) N1 0.0235(12) 0.0200(11) 0.0165(11) 0.0010(9) 0.0001(9) 0.0023(9) N7 0.068(2) 0.0190(13) 0.0452(19) -0.0143(13) -0.0406(16) 0.0147(14) C3 0.0157(12) 0.0208(13) 0.0145(12) 0.0007(10) 0.0033(9) -0.0030(10) O3 0.097(2) 0.0200(12) 0.107(3) -0.0162(15) -0.087(2) 0.0122(15) C2 0.0280(15) 0.0200(14) 0.0231(14) -0.0013(11) 0.0035(12) 0.0065(12) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 N6 1.237(3) . ? N9 C3 1.337(3) . ? N9 N10 1.401(3) . ? N9 H9 0.86(4) . ? O2 N6 1.287(3) . ? N4 N3 1.322(3) . ? N4 C1 1.351(3) . ? N5 N6 1.304(3) . ? N5 C1 1.387(3) . ? N8 N7 1.377(3) . ? N8 H8A 0.95(4) . ? N8 H8C 0.88(5) . ? N8 H8B 0.98(6) . ? N10 H10B 0.90(4) . ? N10 H10A 0.87(4) . ? N2 N3 1.313(3) . ? N2 N1 1.336(3) . ? N2 C2 1.456(3) . ? C1 N1 1.334(3) . ? N7 C3 1.348(4) . ? N7 H7 0.80(4) . ? C3 O3 1.186(3) . ? C2 H2B 0.97(4) . ? C2 H2A 0.98(3) . ? C2 H2C 0.98(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 N9 N10 119.5(2) . . ? C3 N9 H9 117(2) . . ? N10 N9 H9 122(2) . . ? N3 N4 C1 106.1(2) . . ? N6 N5 C1 117.5(2) . . ? N7 N8 H8A 111(2) . . ? N7 N8 H8C 108(3) . . ? H8A N8 H8C 111(4) . . ? N7 N8 H8B 109(3) . . ? H8A N8 H8B 113(4) . . ? H8C N8 H8B 106(4) . . ? N9 N10 H10B 106(2) . . ? N9 N10 H10A 108(2) . . ? H10B N10 H10A 110(3) . . ? N3 N2 N1 114.3(2) . . ? N3 N2 C2 123.2(2) . . ? N1 N2 C2 122.4(2) . . ? N1 C1 N4 112.3(2) . . ? N1 C1 N5 132.2(2) . . ? N4 C1 N5 115.4(2) . . ? N2 N3 N4 106.1(2) . . ? O1 N6 O2 119.9(2) . . ? O1 N6 N5 125.9(2) . . ? O2 N6 N5 114.2(2) . . ? C1 N1 N2 101.1(2) . . ? C3 N7 N8 119.6(3) . . ? C3 N7 H7 123(3) . . ? N8 N7 H7 117(3) . . ? O3 C3 N9 125.2(3) . . ? O3 C3 N7 119.3(3) . . ? N9 C3 N7 115.5(2) . . ? N2 C2 H2B 107(2) . . ? N2 C2 H2A 110(2) . . ? H2B C2 H2A 108(3) . . ? N2 C2 H2C 108(2) . . ? H2B C2 H2C 117(3) . . ? H2A C2 H2C 107(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N3 N4 C1 N1 -0.2(3) . . . . ? N3 N4 C1 N5 177.5(2) . . . . ? N6 N5 C1 N1 -9.6(4) . . . . ? N6 N5 C1 N4 173.2(2) . . . . ? N1 N2 N3 N4 -0.2(3) . . . . ? C2 N2 N3 N4 -177.6(2) . . . . ? C1 N4 N3 N2 0.2(3) . . . . ? C1 N5 N6 O1 -5.3(4) . . . . ? C1 N5 N6 O2 174.8(2) . . . . ? N4 C1 N1 N2 0.1(3) . . . . ? N5 C1 N1 N2 -177.1(3) . . . . ? N3 N2 N1 C1 0.0(3) . . . . ? C2 N2 N1 C1 177.5(2) . . . . ? N10 N9 C3 O3 4.9(5) . . . . ? N10 N9 C3 N7 -176.1(3) . . . . ? N8 N7 C3 O3 0.6(6) . . . . ? N8 N7 C3 N9 -178.5(3) . . . . ? loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag ? ? ? ? ? ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N9 H9 O2 0.86(4) 1.96(4) 2.774(3) 157(3) 4_666 N7 H7 O2 0.80(4) 2.24(4) 2.895(3) 140(3) 4_666 N7 H7 O3 0.80(4) 2.27(4) 2.911(4) 137(3) 4_666 N10 H10B N4 0.90(4) 2.36(4) 3.243(3) 168(3) 4_565 N10 H10B N5 0.90(4) 2.69(3) 3.325(3) 128(3) 4_565 N10 H10A O1 0.87(4) 2.47(4) 3.179(3) 138(3) 4_566 N8 H8A N10 0.95(4) 1.93(4) 2.852(3) 164(3) 4_666 N8 H8A O3 0.95(4) 2.52(4) 3.119(3) 121(3) 4_666 N8 H8C N5 0.88(5) 2.26(5) 3.022(3) 145(4) . N8 H8B O2 0.98(6) 1.85(6) 2.793(3) 161(5) 1_655 N8 H8B N5 0.98(6) 2.54(5) 3.182(3) 123(4) 1_655 N8 H8B N6 0.98(6) 2.60(6) 3.477(4) 148(4) 1_655 _geom_special_details ? #===END