data_OTH019 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H16 N4' _chemical_formula_weight 264.33 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' _symmetry_cell_setting tetragonal _symmetry_space_group_name_H-M I41/a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-y+3/4, x+1/4, z+1/4' 'y+3/4, -x+3/4, z+3/4' 'x+1/2, y+1/2, z+1/2' '-x+1, -y+1/2, z+1' '-y+5/4, x+3/4, z+3/4' 'y+5/4, -x+5/4, z+5/4' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'y-3/4, -x-1/4, -z-1/4' '-y-3/4, x-3/4, -z-3/4' '-x+1/2, -y+1/2, -z+1/2' 'x, y+1/2, -z' 'y-1/4, -x+1/4, -z+1/4' '-y-1/4, x-1/4, -z-1/4' _cell_length_a 12.8618(11) _cell_length_b 12.8618(11) _cell_length_c 17.9097(17) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2962.7(5) _cell_formula_units_Z 8 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.185 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1120 _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9854 _exptl_absorpt_correction_T_max 0.9891 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Stoe IPDS' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14083 _diffrn_reflns_av_R_equivalents 0.0682 _diffrn_reflns_av_sigmaI/netI 0.0555 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.17 _diffrn_reflns_theta_max 26.20 _reflns_number_total 1480 _reflns_number_gt 834 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'IPDS (Stoe, 1999)' _computing_cell_refinement 'IPDS (Stoe, 1999)' _computing_data_reduction 'XRED (Stoe, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia,1997)' _computing_publication_material 'SHELX-97 (Sheldrick, 1997)' _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 _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0204P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _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_number_reflns 1480 _refine_ls_number_parameters 123 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0634 _refine_ls_R_factor_gt 0.0260 _refine_ls_wR_factor_ref 0.0465 _refine_ls_wR_factor_gt 0.0423 _refine_ls_goodness_of_fit_ref 0.731 _refine_ls_restrained_S_all 0.731 _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 N1 N 0.46097(7) 0.21244(8) 0.05445(5) 0.0395(3) Uani 1 1 d . . . H1N H 0.4699(9) 0.1534(10) 0.0910(7) 0.063(4) Uiso 1 1 d . . . N2 N 0.21129(7) 0.22542(8) -0.09476(5) 0.0419(3) Uani 1 1 d . . . C1 C 0.37970(8) 0.21981(8) 0.00624(6) 0.0310(3) Uani 1 1 d . . . C2 C 0.30270(8) 0.14203(9) 0.00603(6) 0.0348(3) Uani 1 1 d . . . H2 H 0.3059(8) 0.0741(8) 0.0415(6) 0.036(3) Uiso 1 1 d . . . C3 C 0.22277(9) 0.14868(10) -0.04433(7) 0.0391(3) Uani 1 1 d . . . H3 H 0.1672(9) 0.0952(9) -0.0431(6) 0.049(4) Uiso 1 1 d . . . C4 C 0.28472(9) 0.29968(10) -0.09282(7) 0.0400(3) Uani 1 1 d . . . H4 H 0.2778(9) 0.3552(8) -0.1296(6) 0.043(3) Uiso 1 1 d . . . C5 C 0.36783(9) 0.30098(9) -0.04484(6) 0.0351(3) Uani 1 1 d . . . H5 H 0.4187(9) 0.3569(8) -0.0460(6) 0.044(3) Uiso 1 1 d . . . C6 C 0.28538(11) 0.30192(10) 0.18788(7) 0.0483(3) Uani 1 1 d . . . H6 H 0.3097(9) 0.3386(9) 0.1431(7) 0.060(4) Uiso 1 1 d . . . C7 C 0.19456(11) 0.24565(10) 0.18414(7) 0.0490(3) Uani 1 1 d . . . H7 H 0.1544(10) 0.2418(9) 0.1364(7) 0.064(4) Uiso 1 1 d . . . C8 C 0.15876(10) 0.19371(10) 0.24660(8) 0.0502(3) Uani 1 1 d . . . H8 H 0.0951(10) 0.1555(10) 0.2417(7) 0.062(4) 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 N1 0.0324(5) 0.0453(6) 0.0409(5) 0.0080(5) -0.0035(5) -0.0120(4) N2 0.0346(6) 0.0520(7) 0.0390(6) -0.0022(5) 0.0003(5) 0.0001(5) C1 0.0290(6) 0.0356(6) 0.0284(6) -0.0017(5) 0.0055(5) -0.0020(5) C2 0.0318(6) 0.0361(6) 0.0365(7) 0.0015(6) 0.0047(6) -0.0056(5) C3 0.0316(6) 0.0442(7) 0.0414(7) -0.0042(6) 0.0062(6) -0.0072(6) C4 0.0392(7) 0.0448(7) 0.0360(7) 0.0064(6) 0.0058(6) 0.0049(6) C5 0.0319(7) 0.0359(7) 0.0375(7) 0.0018(6) 0.0071(6) -0.0045(6) C6 0.0592(9) 0.0396(7) 0.0462(8) 0.0047(6) 0.0171(7) 0.0028(6) C7 0.0540(9) 0.0466(8) 0.0465(8) -0.0003(6) 0.0026(7) 0.0059(7) C8 0.0459(8) 0.0464(8) 0.0583(9) -0.0029(7) 0.0098(7) -0.0022(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 N1 C1 1.3591(14) . ? N1 N1 1.3934(18) 6_554 ? N1 H1N 1.010(13) . ? N2 C4 1.3437(15) . ? N2 C3 1.3461(16) . ? C1 C5 1.3965(15) . ? C1 C2 1.4078(14) . ? C2 C3 1.3702(16) . ? C2 H2 1.081(11) . ? C3 H3 0.992(12) . ? C4 C5 1.3716(16) . ? C4 H4 0.975(11) . ? C5 H5 0.972(11) . ? C6 C7 1.3758(18) . ? C6 C8 1.3770(19) 13 ? C6 H6 0.982(13) . ? C7 C8 1.3818(18) . ? C7 H7 1.001(13) . ? C8 C6 1.3770(19) 13 ? C8 H8 0.959(13) . ? 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 N1 120.39(9) . 6_554 ? C1 N1 H1N 123.5(7) . . ? N1 N1 H1N 116.1(7) 6_554 . ? C4 N2 C3 115.26(11) . . ? N1 C1 C5 123.53(10) . . ? N1 C1 C2 119.55(10) . . ? C5 C1 C2 116.91(11) . . ? C3 C2 C1 119.02(11) . . ? C3 C2 H2 117.8(5) . . ? C1 C2 H2 123.1(6) . . ? N2 C3 C2 124.74(12) . . ? N2 C3 H3 116.4(7) . . ? C2 C3 H3 118.8(7) . . ? N2 C4 C5 124.94(12) . . ? N2 C4 H4 116.0(7) . . ? C5 C4 H4 119.0(7) . . ? C4 C5 C1 119.11(11) . . ? C4 C5 H5 121.3(6) . . ? C1 C5 H5 119.6(6) . . ? C7 C6 C8 120.40(13) . 13 ? C7 C6 H6 118.9(7) . . ? C8 C6 H6 120.7(7) 13 . ? C6 C7 C8 119.85(13) . . ? C6 C7 H7 120.4(7) . . ? C8 C7 H7 119.8(7) . . ? C6 C8 C7 119.75(13) 13 . ? C6 C8 H8 123.0(8) 13 . ? C7 C8 H8 117.2(8) . . ? 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 N1 N1 C1 C5 -0.65(17) 6_554 . . . ? N1 N1 C1 C2 178.70(10) 6_554 . . . ? N1 C1 C2 C3 -178.09(10) . . . . ? C5 C1 C2 C3 1.30(16) . . . . ? C4 N2 C3 C2 -0.83(17) . . . . ? C1 C2 C3 N2 -0.17(17) . . . . ? C3 N2 C4 C5 0.69(18) . . . . ? N2 C4 C5 C1 0.44(18) . . . . ? N1 C1 C5 C4 177.94(11) . . . . ? C2 C1 C5 C4 -1.42(16) . . . . ? C8 C6 C7 C8 0.4(2) 13 . . . ? C6 C7 C8 C6 -0.4(2) . . . 13 ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.20 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.131 _refine_diff_density_min -0.110 _refine_diff_density_rms 0.021