Crystal structure of 3-((1H-benzo[d]imidazol-2-yl)amino)-2-(1H-benzo[d]imidazol-2-yl)isoindolin-1-one, C22H16N6O
Zeng, Dai; Xing, Ai-Ping; Wei, Jun-Jun; Chu, Yi-Xin; Zhang, Shu-Ling; Zeitschrift für Kristallographie - New Crystal Structures 234 (2019) 249–251; doi:10.1515/ncrs-2018-0286

data_8105607
_publ_section_title
;
 Crystal structure of
 3-((1H-benzo[d]imidazol-2-yl)amino)-2-(1H-benzo[d]imidazol-2-yl)isoindolin-1-one,
 C22H16N6O
;
_journal_issue                   2
_journal_name_full
'Zeitschrift f\"ur Kristallographie - New Crystal Structures'
_journal_page_first              249
_journal_page_last               251
_journal_paper_doi               10.1515/ncrs-2018-0286
_journal_volume                  234
_journal_year                    2019
_chemical_formula_moiety         'C22 H16 N6 O'
_chemical_formula_sum            'C22 H16 N6 O'
_chemical_formula_weight         380.41
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 102.345(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.2081(5)
_cell_length_b                   23.3620(11)
_cell_length_c                   12.2769(5)
_cell_measurement_reflns_used    2528
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      60.4970
_cell_measurement_theta_min      3.9160
_cell_volume                     3700.7(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega -106.00  -76.00   0.5000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000  -60.0000 60

  2 omega  -82.00  -14.00   0.5000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -77.0000  120.0000 136

  3 omega  -47.00  -15.00   0.5000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   37.0000  120.0000 64

  4 omega   16.00   59.00   0.5000   13.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5461   37.0000  -30.0000 86

  5 omega   70.00  104.00   0.5000   13.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5461   57.0000  -90.0000 68

  6 omega   22.00  106.00   0.5000   13.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5461   37.0000 -120.0000 168

  7 omega  -12.00   34.00   0.5000   13.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5461  -57.0000   30.0000 92

  8 omega   66.00   93.00   0.5000   13.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5461  178.0000 -150.0000 54

  9 omega   24.00   62.00   0.5000   13.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5461   57.0000  -90.0000 76

 10 omega   33.00   76.00   0.5000   13.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5461  -99.0000  -60.0000 86

 11 omega   58.00  111.00   0.5000   13.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5461  178.0000  -90.0000 106

 12 omega   82.00  107.00   0.5000   13.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5461   37.0000  -30.0000 50

 13 omega  -34.00   29.00   0.5000   13.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5461  -19.0000   60.0000 126

 14 omega   81.00  159.00   0.5000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -90.0000 156

 15 omega   47.00   89.00   0.5000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -180.0000 84

 16 omega   37.00   86.00   0.5000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   90.0000 98

 17 omega   38.00  109.00   0.5000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  150.0000 142

 18 omega   39.00   89.00   0.5000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  150.0000 100

 19 omega   38.00   86.00   0.5000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -60.0000 96

 20 omega   44.00   87.00   0.5000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -90.0000 86

 21 omega  111.00  145.00   0.5000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -180.0000 68

 22 omega   46.00  110.00   0.5000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  150.0000 128

 23 omega   84.00  170.00   0.5000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000 -120.0000 172
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0195275000
_diffrn_orient_matrix_UB_12      0.0593831000
_diffrn_orient_matrix_UB_13      0.0549330000
_diffrn_orient_matrix_UB_21      0.0020784000
_diffrn_orient_matrix_UB_22      0.0267096000
_diffrn_orient_matrix_UB_23      -0.1142595000
_diffrn_orient_matrix_UB_31      -0.1177960000
_diffrn_orient_matrix_UB_32      0.0103047000
_diffrn_orient_matrix_UB_33      -0.0207572000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_av_unetI/netI     0.0644
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16853
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.083
_diffrn_reflns_theta_max         67.083
_diffrn_reflns_theta_min         3.784
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.720
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81322
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_description       prism
_exptl_crystal_F_000             1584
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       0.00072(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     544
_refine_ls_number_reflns         6602
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.1191
_refine_ls_R_factor_gt           0.0648
_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/[\s^2^(Fo^2^)+(0.0657P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1400
_refine_ls_wR_factor_ref         0.1730
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3589
_reflns_number_total             6602
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            suppl_ncrs-2018-0286_suppl.cif
_cod_data_source_block           2
_cod_database_code               8105607
_shelx_estimated_absorpt_t_max   0.945
_shelx_estimated_absorpt_t_min   0.931
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C8'(H8')
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2A), C3(H3), C4(H4A), C12(H12), C13(H13), C14(H14), C15(H15),
 C19(H19), C20(H20), C21(H21), C22(H22), N4(H4), C1'(H1'), C2'(H2'A), C3'(H3'),
 C4'(H4'A), C12'(H12'), C13'(H13'), C14'(H14'), C15'(H15'), C19'(H19'),
 C20'(H20'), C21'(H21'), C22'(H22')
;