####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################
#
# Deposited by Min Guo as a neutral hydrate with refcode YOTYOW
# and published as Acta Cryst. (2009) E65, o1403.
# Now re-refined as ammonium salt. Ammonium chloride was a reagent
# in the original synthesis.
#
#######################################################################
data_I
_audit_block_doi                 10.5517/ccss7wn
_database_code_depnum_ccdc_archive 'CCDC 738292'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1107/S1600536809017899 2009 

data_shelx
 
_audit_creation_method            'SHELXL-2014/7'
_shelx_SHELXL_version_number      '2014/7'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C5 H3 N10 1-, H4 N 1+'
_chemical_formula_sum
 'C5 H7 N11' 
_chemical_formula_weight          221.22

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'
 
_space_group_crystal_system       monoclinic
_space_group_IT_number            14
_space_group_name_H-M_alt         'P 21/c'
_space_group_name_Hall            '-P 2ybc'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y-1/2, z-1/2'
 
_cell_length_a                    15.607(3)
_cell_length_b                    3.6706(7)
_cell_length_c                    18.127(7)
_cell_angle_alpha                 90
_cell_angle_beta                  119.13(2)
_cell_angle_gamma                 90
_cell_volume                      907.1(5)
_cell_formula_units_Z             4
_cell_measurement_temperature     294(2)
_cell_measurement_reflns_used     2076
_cell_measurement_theta_min       1.97
_cell_measurement_theta_max       27.54
 
_exptl_crystal_description        Block
_exptl_crystal_colour             Colourless
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.620          
_exptl_crystal_F_000              456
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.08
_exptl_crystal_size_mid           0.08
_exptl_crystal_size_min           0.03
_exptl_absorpt_coefficient_mu     0.122
_shelx_estimated_absorpt_T_min    ?
_shelx_estimated_absorpt_T_max    ?
_exptl_absorpt_correction_type    Multi-scan
_exptl_absorpt_correction_T_min   0.892
_exptl_absorpt_correction_T_max   0.990
_exptl_absorpt_process_details    '(CrystalClear; Rigaku, 2005)'
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       294(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    ?
_diffrn_measurement_device_type   'Rigaku SCXmini'
_diffrn_measurement_method        ?
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             1785
_diffrn_reflns_av_unetI/netI      0.0462
_diffrn_reflns_av_R_equivalents   0.0605
_diffrn_reflns_limit_h_min        -19
_diffrn_reflns_limit_h_max        19
_diffrn_reflns_limit_k_min        0
_diffrn_reflns_limit_k_max        4
_diffrn_reflns_limit_l_min        0
_diffrn_reflns_limit_l_max        22
_diffrn_reflns_theta_min          3.550
_diffrn_reflns_theta_max          25.993
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.997
_diffrn_measured_fraction_theta_full  0.997
_diffrn_reflns_Laue_measured_fraction_max    0.997
_diffrn_reflns_Laue_measured_fraction_full   0.997
_diffrn_reflns_point_group_measured_fraction_max   0.997
_diffrn_reflns_point_group_measured_fraction_full  0.997
_reflns_number_total              1785
_reflns_number_gt                 1362
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        ?
_computing_cell_refinement        ?
_computing_data_reduction         ?
_computing_structure_solution     ?
_computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics     ?
_computing_publication_material   ?
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0548P)²+0.2327P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    difmap
_refine_ls_hydrogen_treatment     refall
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          1785
_refine_ls_number_parameters      173
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0719
_refine_ls_R_factor_gt            0.0490
_refine_ls_wR_factor_ref          0.1176
_refine_ls_wR_factor_gt           0.1072
_refine_ls_goodness_of_fit_ref    1.055
_refine_ls_restrained_S_all       1.055
_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_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
N11 N 0.66671(15) 1.0091(6) 0.61956(13) 0.0283(5) Uani 1 1 d . . . . .
N5 N 0.49754(12) 0.4358(5) 0.67750(11) 0.0340(5) Uani 1 1 d . . . . .
N6 N 0.40297(12) 0.3465(5) 0.64874(11) 0.0293(5) Uani 1 1 d . . . . .
H6A H 0.3745(19) 0.257(8) 0.6817(17) 0.064(9) Uiso 1 1 d . . . . .
N9 N 0.23055(13) -0.0387(5) 0.73303(11) 0.0334(5) Uani 1 1 d . . . . .
N10 N 0.26103(12) 0.0906(5) 0.68003(11) 0.0300(5) Uani 1 1 d . . . . .
N1 N 0.09207(13) 0.2432(5) 0.45263(11) 0.0296(5) Uani 1 1 d . . . . .
H1A H 0.029(2) 0.162(8) 0.4416(16) 0.055(8) Uiso 1 1 d . . . . .
N7 N 0.10100(13) 0.0035(5) 0.61044(11) 0.0331(5) Uani 1 1 d . . . . .
N8 N 0.13569(13) -0.0900(6) 0.69184(12) 0.0368(5) Uani 1 1 d . . . . .
N4 N 0.50231(13) 0.5687(5) 0.61338(12) 0.0324(5) Uani 1 1 d . . . . .
N2 N 0.20799(12) 0.4485(5) 0.42628(11) 0.0294(5) Uani 1 1 d . . . . .
N3 N 0.41278(12) 0.5682(5) 0.54272(11) 0.0296(5) Uani 1 1 d . . . . .
C1 C 0.11444(16) 0.3671(7) 0.39411(14) 0.0334(6) Uani 1 1 d . . . . .
H1 H 0.0627(16) 0.390(6) 0.3324(14) 0.034(6) Uiso 1 1 d . . . . .
C5 C 0.35181(14) 0.4278(6) 0.56653(13) 0.0228(5) Uani 1 1 d . . . . .
C4 C 0.17938(14) 0.1147(6) 0.60549(12) 0.0240(5) Uani 1 1 d . . . . .
C2 C 0.24763(14) 0.3690(6) 0.51121(12) 0.0238(5) Uani 1 1 d . . . . .
C3 C 0.17660(14) 0.2411(6) 0.52874(12) 0.0240(5) Uani 1 1 d . . . . .
H11A H 0.6366(19) 1.138(8) 0.5680(18) 0.056(8) Uiso 1 1 d . . . . .
H11B H 0.7150(19) 0.857(8) 0.6159(16) 0.055(8) Uiso 1 1 d . . . . .
H11C H 0.617(2) 0.881(8) 0.6206(17) 0.058(8) Uiso 1 1 d . . . . .
H11D H 0.7007(18) 1.161(8) 0.6693(17) 0.054(8) Uiso 1 1 d . . . . .
 
 
_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
N11 H11A 0.94(3) . ?
N11 H11B 0.97(3) . ?
N11 H11C 0.91(3) . ?
N11 H11D 0.97(3) . ?
N5 N4 1.296(3) . ?
N5 N6 1.345(2) . ?
N6 C5 1.337(3) . ?
N6 H6A 0.96(3) . ?
N9 N8 1.307(3) . ?
N9 N10 1.349(2) . ?
N10 C4 1.334(3) . ?
N1 C1 1.347(3) . ?
N1 C3 1.368(3) . ?
N1 H1A 0.95(3) . ?
N7 C4 1.333(3) . ?
N7 N8 1.345(3) . ?
N4 N3 1.360(2) . ?
N2 C1 1.316(3) . ?
N2 C2 1.382(3) . ?
N3 C5 1.326(3) . ?
C1 H1 1.02(2) . ?
C5 C2 1.452(3) . ?
C4 C3 1.447(3) . ?
C2 C3 1.376(3) . ?
 
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
H11A N11 H11B 105(2) . . ?
H11A N11 H11C 105(2) . . ?
H11B N11 H11C 114(2) . . ?
H11A N11 H11D 115(2) . . ?
H11B N11 H11D 108(2) . . ?
H11C N11 H11D 111(2) . . ?
N4 N5 N6 105.99(17) . . ?
C5 N6 N5 108.95(18) . . ?
C5 N6 H6A 124.3(15) . . ?
N5 N6 H6A 126.6(15) . . ?
N8 N9 N10 109.74(17) . . ?
C4 N10 N9 104.50(16) . . ?
C1 N1 C3 107.68(18) . . ?
C1 N1 H1A 125.3(16) . . ?
C3 N1 H1A 127.0(16) . . ?
C4 N7 N8 105.03(17) . . ?
N9 N8 N7 109.21(17) . . ?
N5 N4 N3 111.29(16) . . ?
C1 N2 C2 104.13(17) . . ?
C5 N3 N4 105.36(17) . . ?
N2 C1 N1 112.61(19) . . ?
N2 C1 H1 125.8(12) . . ?
N1 C1 H1 121.6(12) . . ?
N3 C5 N6 108.41(18) . . ?
N3 C5 C2 124.95(19) . . ?
N6 C5 C2 126.64(19) . . ?
N7 C4 N10 111.51(18) . . ?
N7 C4 C3 124.31(18) . . ?
N10 C4 C3 124.17(18) . . ?
C3 C2 N2 110.80(17) . . ?
C3 C2 C5 130.42(19) . . ?
N2 C2 C5 118.78(18) . . ?
N1 C3 C2 104.77(18) . . ?
N1 C3 C4 122.29(18) . . ?
C2 C3 C4 132.92(18) . . ?
 
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
N4 N5 N6 C5 0.1(2) . . . . ?
N8 N9 N10 C4 0.3(2) . . . . ?
N10 N9 N8 N7 0.1(3) . . . . ?
C4 N7 N8 N9 -0.5(2) . . . . ?
N6 N5 N4 N3 -0.1(2) . . . . ?
N5 N4 N3 C5 0.1(2) . . . . ?
C2 N2 C1 N1 0.2(3) . . . . ?
C3 N1 C1 N2 -0.2(3) . . . . ?
N4 N3 C5 N6 0.0(2) . . . . ?
N4 N3 C5 C2 -179.05(18) . . . . ?
N5 N6 C5 N3 -0.1(2) . . . . ?
N5 N6 C5 C2 178.94(19) . . . . ?
N8 N7 C4 N10 0.6(2) . . . . ?
N8 N7 C4 C3 179.8(2) . . . . ?
N9 N10 C4 N7 -0.6(2) . . . . ?
N9 N10 C4 C3 -179.8(2) . . . . ?
C1 N2 C2 C3 -0.1(2) . . . . ?
C1 N2 C2 C5 179.90(19) . . . . ?
N3 C5 C2 C3 -177.0(2) . . . . ?
N6 C5 C2 C3 4.2(4) . . . . ?
N3 C5 C2 N2 3.0(3) . . . . ?
N6 C5 C2 N2 -175.9(2) . . . . ?
C1 N1 C3 C2 0.1(2) . . . . ?
C1 N1 C3 C4 -178.6(2) . . . . ?
N2 C2 C3 N1 0.0(2) . . . . ?
C5 C2 C3 N1 180.0(2) . . . . ?
N2 C2 C3 C4 178.5(2) . . . . ?
C5 C2 C3 C4 -1.5(4) . . . . ?
N7 C4 C3 N1 -2.7(3) . . . . ?
N10 C4 C3 N1 176.4(2) . . . . ?
N7 C4 C3 C2 179.0(2) . . . . ?
N10 C4 C3 C2 -1.9(4) . . . . ?
 
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 
N6 H6A N5  0.96(3) 2.63(3) 3.137(3) 113.1(18) 2_646
N6 H6A N10  0.96(3) 1.86(3) 2.708(2) 146(2) .
N1 H1A N7  0.95(3) 1.87(3) 2.802(3) 164(2) 3_556
N1 H1A N8  0.95(3) 2.54(3) 3.278(3) 134(2) 3_556
N11 H11A N3  0.94(3) 2.07(3) 3.008(3) 173(2) 3_676
N11 H11B N2  0.97(3) 2.05(3) 2.986(3) 164(2) 3_666
N11 H11C N4  0.91(3) 2.08(3) 2.988(3) 175(2) .
N11 H11D N9  0.97(3) 1.91(3) 2.880(3) 179(2) 2_666
 
_refine_diff_density_max    0.224
_refine_diff_density_min   -0.283
_refine_diff_density_rms    0.058



