#------------------------------------------------------------------------------
#$Date: 2023-05-10 10:23:18 +0300 (Wed, 10 May 2023) $
#$Revision: 283646 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/71/8107163.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8107163
loop_
_publ_author_name
'Ma, Hang'
'Tian, Qiang'
'Wan, Banglong'
_publ_section_title
;
 The crystal structure of 1H-benzimidazole-2-carboxamide, C8H7N3O
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              599
_journal_page_last               600
_journal_paper_doi               10.1515/ncrs-2022-0159
_journal_volume                  237
_journal_year                    2022
_chemical_formula_moiety         'C8 H7 N3 O'
_chemical_formula_sum            'C8 H7 N3 O'
_chemical_formula_weight         161.17
_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_Hall           '-P 2ab 2ac'
_space_group_name_H-M_alt        'P c c n'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.9071(14)
_cell_length_b                   11.1950(19)
_cell_length_c                   13.315(2)
_cell_measurement_reflns_used    744
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      38.38
_cell_measurement_theta_min      5.78
_cell_volume                     1476.8(4)
_computing_cell_refinement       'SAINT V8.40B Bruker-AXS,(Bruker, 2018)'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'SAINT V8.40B Bruker-AXS, (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XM  (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker Photon III 28 detector'
_diffrn_detector_area_resol_mean ' 7.39 for PHOTON III'
_diffrn_detector_type            'Bruker Photon III 28'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device       'Bruker D8 Venture'
_diffrn_measurement_device_type  'Bruker Photon III'
_diffrn_measurement_method       'Profile data from θ/2θ scans'
_diffrn_radiation_monochromator  'Metaljet Helios MX'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     1.34139
_diffrn_radiation_xray_symbol    'Ga K\a'
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8081
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         61.697
_diffrn_reflns_theta_min         5.187
_diffrn_source                   'METALJET liquid metal X-ray source'
_diffrn_source_current           3.57
_diffrn_source_power             0.2497215
_diffrn_source_target            Ga
_diffrn_source_type              'Sealed X-ray tube'
_diffrn_source_voltage           69.95
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.533
_exptl_absorpt_correction_T_max  0.7520
_exptl_absorpt_correction_T_min  0.6653
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v.2.10 (Bruker,2008).'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1691
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0356
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0618P)²+0.3441P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1007
_refine_ls_wR_factor_ref         0.1034
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1509
_reflns_number_total             1691
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2022-0159_suppl.cif
_cod_data_source_block           2
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the built-in table derived from the CIF
Core dictionary named 'cif_core.dic' version 2.4.5 last updated on
2014-11-21.

Automatic conversion script
Id: cif_fix_values 8738 2021-04-28 16:35:53Z antanas 
;
_cod_database_code               8107163
_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.
;
_shelx_estimated_absorpt_t_max   0.949
_shelx_estimated_absorpt_t_min   0.939
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y, -z+1/2'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y+1/2, z'
'-x, -y, -z'
'-x-1/2, y, z-1/2'
'x, -y-1/2, z-1/2'
'x-1/2, y-1/2, -z'
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
C1 C 0.50766(9) 0.82548(9) 0.45016(7) 0.0183(2) Uani 1 1 d . . . . .
C2 C 0.50008(8) 0.69893(9) 0.41662(7) 0.0173(2) Uani 1 1 d . . . . .
C3 C 0.57099(9) 0.51930(8) 0.37837(7) 0.0175(2) Uani 1 1 d . . . . .
C4 C 0.43181(9) 0.53106(8) 0.35948(7) 0.0179(2) Uani 1 1 d . . . . .
C5 C 0.35760(10) 0.43400(9) 0.32256(8) 0.0213(2) Uani 1 1 d . . . . .
H5 H 0.263559 0.440423 0.309687 0.026 Uiso 1 1 calc R U . . .
C6 C 0.42643(11) 0.32863(9) 0.30559(8) 0.0231(2) Uani 1 1 d . . . . .
H6 H 0.378376 0.261133 0.281264 0.028 Uiso 1 1 calc R U . . .
C7 C 0.56638(11) 0.31875(9) 0.32350(8) 0.0236(2) Uani 1 1 d . . . . .
H7 H 0.610441 0.245159 0.309799 0.028 Uiso 1 1 calc R U . . .
C8 C 0.64090(10) 0.41319(9) 0.36040(8) 0.0219(2) Uani 1 1 d . . . . .
H8 H 0.734978 0.406334 0.372937 0.026 Uiso 1 1 calc R U . . .
N1 N 0.39305(8) 0.88550(8) 0.44704(7) 0.0220(2) Uani 1 1 d . . . . .
H1A H 0.3935(12) 0.9645(12) 0.4656(10) 0.026 Uiso 1 1 d . U . . .
H1B H 0.3168(13) 0.8534(11) 0.4233(10) 0.026 Uiso 1 1 d . U . . .
N2 N 0.61178(8) 0.62859(7) 0.41480(7) 0.0180(2) Uani 1 1 d . . . . .
H2 H 0.6937(12) 0.6446(10) 0.4385(9) 0.022 Uiso 1 1 d . U . . .
N3 N 0.38985(8) 0.64568(7) 0.38417(7) 0.0185(2) Uani 1 1 d . . . . .
O1 O 0.61756(6) 0.86763(6) 0.47894(6) 0.0214(2) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
N1 C1 C2 115.59(8) . .
O1 C1 C2 119.79(8) . .
O1 C1 N1 124.62(9) . .
N2 C2 C1 121.09(8) . .
N3 C2 C1 124.85(8) . .
N3 C2 N2 114.03(9) . .
C8 C3 C4 122.34(9) . .
N2 C3 C4 105.51(8) . .
N2 C3 C8 132.15(9) . .
C5 C4 C3 120.28(9) . .
N3 C4 C3 109.72(8) . .
N3 C4 C5 130.00(9) . .
C4 C5 H5 121.3 . .
C6 C5 C4 117.43(9) . .
C6 C5 H5 121.3 . .
C5 C6 H6 119.2 . .
C5 C6 C7 121.63(9) . .
C7 C6 H6 119.2 . .
C6 C7 H7 119.1 . .
C8 C7 C6 121.72(9) . .
C8 C7 H7 119.1 . .
C3 C8 H8 121.7 . .
C7 C8 C3 116.59(9) . .
C7 C8 H8 121.7 . .
C1 N1 H1A 118.5(8) . .
C1 N1 H1B 122.3(8) . .
H1A N1 H1B 119.1(11) . .
C2 N2 C3 106.40(8) . .
C2 N2 H2 128.3(8) . .
C3 N2 H2 124.9(7) . .
C2 N3 C4 104.35(8) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.4874(14) .
C1 N1 1.3200(12) .
C1 O1 1.2470(11) .
C2 N2 1.3585(12) .
C2 N3 1.3171(12) .
C3 C4 1.4078(14) .
C3 C8 1.3957(13) .
C3 N2 1.3767(12) .
C4 C5 1.4010(13) .
C4 N3 1.3884(12) .
C5 H5 0.9500 .
C5 C6 1.3812(14) .
C6 H6 0.9500 .
C6 C7 1.4112(16) .
C7 H7 0.9500 .
C7 C8 1.3800(14) .
C8 H8 0.9500 .
N1 H1A 0.919(14) .
N1 H1B 0.895(13) .
N2 H2 0.889(12) .
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
_geom_hbond_publ_flag
N1 H1A O1 0.919(14) 2.022(14) 2.9361(12) 173.3(12) 5_676 yes
N1 H1B N3 0.895(13) 2.112(13) 2.9459(12) 154.7(11) 4_565 yes
N2 H2 O1 0.889(12) 1.951(12) 2.8145(11) 163.5(11) 4_665 yes
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
C1 C2 N2 C3 -178.64(9) . . . .
C1 C2 N3 C4 178.58(9) . . . .
C3 C4 C5 C6 -0.25(15) . . . .
C3 C4 N3 C2 -0.22(11) . . . .
C4 C3 C8 C7 -0.46(15) . . . .
C4 C3 N2 C2 0.16(10) . . . .
C4 C5 C6 C7 -0.69(16) . . . .
C5 C4 N3 C2 178.86(10) . . . .
C5 C6 C7 C8 1.10(16) . . . .
C6 C7 C8 C3 -0.49(15) . . . .
C8 C3 C4 C5 0.85(15) . . . .
C8 C3 C4 N3 -179.97(9) . . . .
C8 C3 N2 C2 -179.84(10) . . . .
N1 C1 C2 N2 178.87(9) . . . .
N1 C1 C2 N3 0.74(15) . . . .
N2 C2 N3 C4 0.34(12) . . . .
N2 C3 C4 C5 -179.14(9) . . . .
N2 C3 C4 N3 0.04(10) . . . .
N2 C3 C8 C7 179.53(10) . . . .
N3 C2 N2 C3 -0.32(12) . . . .
N3 C4 C5 C6 -179.24(9) . . . .
O1 C1 C2 N2 -1.34(15) . . . .
O1 C1 C2 N3 -179.47(9) . . . .
