N-chlorobenzimidazoles as efficient and structurally diverse amphoteric halogen bond donors in crystal engineering
Dhaka, Arun; Jeannin, olivier; Aubert, Emmanuel; Espinosa, Enrique; Fourmigué, Marc; Jeon, Ie-Rang; Chemical Communications  (2022) –; doi:10.1039/D2CC03971K

data_7130616
_publ_section_title
;
 N-chlorobenzimidazoles as efficient and structurally diverse amphoteric
 halogen bond donors in crystal engineering
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC03971K
_journal_year                    2022
_chemical_formula_moiety         'C7 H4 Cl2 N2'
_chemical_formula_sum            'C7 H4 Cl2 N2'
_chemical_formula_weight         187.02
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_creation_date             2022-05-16T10:48:41-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2022-05-17 deposited with the CCDC.	2022-08-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.837(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.9412(15)
_cell_length_b                   9.2207(16)
_cell_length_c                   10.7738(15)
_cell_measurement_reflns_used    1290
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.8
_cell_measurement_theta_min      2.92
_cell_measurement_wavelength     0.71073
_cell_volume                     779.5(2)
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.98
_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_orient_matrix_UB_11      0.109692
_diffrn_orient_matrix_UB_12      -0.011154
_diffrn_orient_matrix_UB_13      0.058693
_diffrn_orient_matrix_UB_21      -0.060614
_diffrn_orient_matrix_UB_22      -0.055456
_diffrn_orient_matrix_UB_23      0.059571
_diffrn_orient_matrix_UB_31      0.023105
_diffrn_orient_matrix_UB_32      -0.092531
_diffrn_orient_matrix_UB_33      -0.042777
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_unetI/netI     0.043
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.98
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4738
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.98
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.481
_diffrn_reflns_theta_min         2.923
_exptl_absorpt_coefficient_mu    0.759
_exptl_absorpt_correction_T_max  0.977
_exptl_absorpt_correction_T_min  0.921
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.594
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     100
_refine_ls_number_reflns         1745
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.079
_refine_ls_R_factor_gt           0.0403
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0282P)^2^+0.3414P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0788
_refine_ls_wR_factor_ref         0.0935
_reflns_Friedel_coverage         0
_reflns_number_gt                1147
_reflns_number_total             1745
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc03971k2.cif
_cod_data_source_block           shelx_CCDC1
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7130616
_shelx_res_checksum              47922
_shelx_hkl_checksum              33470