#------------------------------------------------------------------------------
#$Date: 2022-08-31 00:56:23 +0300 (Wed, 31 Aug 2022) $
#$Revision: 277467 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/06/7130616.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_7130616
loop_
_publ_author_name
'Dhaka, Arun'
'Jeannin, olivier'
'Aubert, Emmanuel'
'Espinosa, Enrique'
'Fourmigué, Marc'
'Jeon, Ie-Rang'
_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/[σ²(Fo²)+(0.0282P)²+0.3414P] where P=(Fo²+2Fc²)/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 > 2σ(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
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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 0.4621(3) 0.0070(3) 0.7045(2) 0.0429(6) Uani 1 1 d . . . . .
C2 C 0.4747(4) -0.1283(3) 0.7617(3) 0.0549(7) Uani 1 1 d . . . . .
H2 H 0.5524 -0.1448 0.8341 0.066 Uiso 1 1 calc R U . . .
C3 C 0.3698(4) -0.2367(3) 0.7089(3) 0.0627(8) Uani 1 1 d . . . . .
H3 H 0.3763 -0.3277 0.7464 0.075 Uiso 1 1 calc R U . . .
C4 C 0.2534(4) -0.2136(3) 0.6000(3) 0.0640(9) Uani 1 1 d . . . . .
H4 H 0.1846 -0.29 0.5664 0.077 Uiso 1 1 calc R U . . .
C5 C 0.2377(4) -0.0806(3) 0.5410(3) 0.0554(8) Uani 1 1 d . . . . .
H5 H 0.16 -0.0645 0.4684 0.066 Uiso 1 1 calc R U . . .
C6 C 0.3441(3) 0.0269(3) 0.5960(2) 0.0413(6) Uani 1 1 d . . . . .
C7 C 0.4869(3) 0.2277(3) 0.6546(2) 0.0443(6) Uani 1 1 d . . . . .
N1 N 0.5503(3) 0.1339(2) 0.73843(19) 0.0476(6) Uani 1 1 d . . . . .
N2 N 0.3631(3) 0.1711(2) 0.56586(17) 0.0435(5) Uani 1 1 d . . . . .
Cl1 Cl 0.24518(8) 0.25870(8) 0.44486(5) 0.0512(2) Uani 1 1 d . . . . .
Cl2 Cl 0.54339(11) 0.40350(8) 0.64964(7) 0.0662(3) 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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 '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'
Cl Cl 0.1484 0.1585 '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
_geom_angle_publ_flag
N1 C1 C2 130.1(2) . . ?
N1 C1 C6 111.0(2) . . ?
C2 C1 C6 119.0(3) . . ?
C3 C2 C1 118.3(3) . . ?
C3 C2 H2 120.9 . . ?
C1 C2 H2 120.9 . . ?
C2 C3 C4 121.5(3) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C5 C4 C3 121.7(3) . . ?
C5 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
C6 C5 C4 115.8(3) . . ?
C6 C5 H5 122.1 . . ?
C4 C5 H5 122.1 . . ?
C5 C6 N2 132.3(2) . . ?
C5 C6 C1 123.8(3) . . ?
N2 C6 C1 103.9(2) . . ?
N1 C7 N2 113.2(2) . . ?
N1 C7 Cl2 126.0(2) . . ?
N2 C7 Cl2 120.8(2) . . ?
C7 N1 C1 104.7(2) . . ?
C7 N2 C6 107.2(2) . . ?
C7 N2 Cl1 127.72(19) . . ?
C6 N2 Cl1 125.00(17) . . ?
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
C1 N1 1.384(3) . ?
C1 C2 1.388(4) . ?
C1 C6 1.393(3) . ?
C2 C3 1.368(4) . ?
C2 H2 0.93 . ?
C3 C4 1.393(4) . ?
C3 H3 0.93 . ?
C4 C5 1.379(4) . ?
C4 H4 0.93 . ?
C5 C6 1.377(4) . ?
C5 H5 0.93 . ?
C6 N2 1.383(3) . ?
C7 N1 1.295(3) . ?
C7 N2 1.365(3) . ?
C7 Cl2 1.685(3) . ?
N2 Cl1 1.689(2) . ?
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 C1 C2 C3 179.3(3) . . . . ?
C6 C1 C2 C3 -0.1(4) . . . . ?
C1 C2 C3 C4 0.4(4) . . . . ?
C2 C3 C4 C5 -0.4(4) . . . . ?
C3 C4 C5 C6 0.2(4) . . . . ?
C4 C5 C6 N2 -178.9(3) . . . . ?
C4 C5 C6 C1 0.1(4) . . . . ?
N1 C1 C6 C5 -179.6(2) . . . . ?
C2 C1 C6 C5 -0.1(4) . . . . ?
N1 C1 C6 N2 -0.4(3) . . . . ?
C2 C1 C6 N2 179.1(2) . . . . ?
N2 C7 N1 C1 -0.7(3) . . . . ?
Cl2 C7 N1 C1 178.9(2) . . . . ?
C2 C1 N1 C7 -178.8(3) . . . . ?
C6 C1 N1 C7 0.6(3) . . . . ?
N1 C7 N2 C6 0.4(3) . . . . ?
Cl2 C7 N2 C6 -179.11(18) . . . . ?
N1 C7 N2 Cl1 177.54(18) . . . . ?
Cl2 C7 N2 Cl1 -2.0(3) . . . . ?
C5 C6 N2 C7 179.1(3) . . . . ?
C1 C6 N2 C7 0.0(3) . . . . ?
C5 C6 N2 Cl1 1.9(4) . . . . ?
C1 C6 N2 Cl1 -177.21(17) . . . . ?
