#------------------------------------------------------------------------------
#$Date: 2022-05-05 11:17:17 +0300 (Thu, 05 May 2022) $
#$Revision: 274917 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/51/8105151.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_8105151
loop_
_publ_author_name
'Shi, Xiao-Ming'
'Li, Shu-Jing'
'Xiao, Li-Na'
'Li, Meng-Jing'
_publ_section_title
;
 Crystal structure of bis(2-propyl-1H-benzo[d]imidazol-3-ium)
 tetrachloridozincate(II), C10H13Cl4N2Zn
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              497
_journal_page_last               499
_journal_paper_doi               10.1515/ncrs-2019-0794
_journal_volume                  235
_journal_year                    2020
_chemical_formula_moiety         '2(C10 H13 N2), Cl4 Zn'
_chemical_formula_sum            'C20 H26 Cl4 N4 Zn'
_chemical_formula_weight         529.66
_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'
_symmetry_Int_Tables_number      14
_cell_angle_alpha                90
_cell_angle_beta                 93.950(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.370(2)
_cell_length_b                   10.0304(14)
_cell_length_c                   17.913(2)
_cell_measurement_reflns_used    5463
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.38
_cell_measurement_theta_min      2.33
_cell_volume                     2396.5(6)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015) [1]'
_computing_data_collection       'Bruker APEX-II'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015) [1]'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009) [4]'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009) [4]'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015) [3]'
_computing_structure_solution    'ShelXT (Sheldrick, 2015) [2]'
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 0.9904
_diffrn_measured_fraction_theta_max 0.9904
_diffrn_measurement_device       'Bruker APEX-II diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1183
_diffrn_reflns_av_unetI/netI     0.0644
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            30175
_diffrn_reflns_theta_full        25.0996
_diffrn_reflns_theta_max         25.10
_diffrn_reflns_theta_min         2.28
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.485
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6336
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0947 before and 0.0699 after correction.
The Ratio of minimum to maximum transmission is 0.8500.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.4679
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1091.8381
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.6362
_refine_diff_density_min         -0.7070
_refine_diff_density_rms         0.1685
_refine_ls_d_res_high            0.8377
_refine_ls_d_res_low             8.9353
_refine_ls_goodness_of_fit_ref   1.0440
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    44
_refine_ls_number_parameters     264
_refine_ls_number_reflns         4219
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0440
_refine_ls_R_factor_all          0.0814
_refine_ls_R_factor_gt           0.0461
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0282P)²+6.4247P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0882
_refine_ls_wR_factor_ref         0.1038
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              15
_reflns_limit_h_min              -15
_reflns_limit_k_max              11
_reflns_limit_k_min              0
_reflns_limit_l_max              21
_reflns_limit_l_min              0
_reflns_number_gt                2983
_reflns_number_total             4219
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            suppl_ncrs-2019-0794_suppl.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               8105151
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2a,H2b), C3(H3a,H3b), C12(H12a,H12b), C13(H13a,H13b)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C17(H17), C18(H18), C19(H19), C20(H20),
 N1(H1), N2(H2), N3(H3), N4(H4)
2.c Idealised Me refined as rotating group:
 C4(H4a,H4b,H4c), C11(H11a,H11b,H11c)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-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_refinement_flags_posn
C1 C 0.8917(3) 0.3322(4) 0.1158(2) 0.0230(10) Uani 1.000000 .
C2 C 0.9052(4) 0.2252(4) 0.1718(2) 0.0309(11) Uani 1.000000 .
H2a H 0.9775(4) 0.2182(4) 0.1875(2) 0.0371(13) Uiso 1.000000 R
H2b H 0.8699(4) 0.2512(4) 0.2164(2) 0.0371(13) Uiso 1.000000 R
C3 C 0.8679(4) 0.0888(5) 0.1464(3) 0.0387(13) Uani 1.000000 .
H3a H 0.7959(4) 0.0944(5) 0.1297(3) 0.0465(15) Uiso 1.000000 R
H3b H 0.9049(4) 0.0594(5) 0.1033(3) 0.0465(15) Uiso 1.000000 R
C4 C 0.8823(4) -0.0132(5) 0.2092(3) 0.0468(14) Uani 1.000000 .
H4a H 0.9540(5) -0.024(3) 0.2228(13) 0.070(2) Uiso 1.000000 GR
H4b H 0.849(2) 0.0181(17) 0.2528(7) 0.070(2) Uiso 1.000000 GR
H4c H 0.853(2) -0.0987(11) 0.1923(7) 0.070(2) Uiso 1.000000 GR
C5 C 0.8778(3) 0.5350(4) 0.0644(2) 0.0215(9) Uani 1.000000 .
C6 C 0.8783(3) 0.4418(4) 0.0067(2) 0.0222(10) Uani 1.000000 .
C7 C 0.8714(3) 0.4792(5) -0.0682(2) 0.0249(10) Uani 1.000000 .
H7 H 0.8705(3) 0.4154(5) -0.1075(2) 0.0298(12) Uiso 1.000000 R
C8 C 0.8658(3) 0.6151(5) -0.0824(3) 0.0319(11) Uani 1.000000 .
H8 H 0.8617(3) 0.6456(5) -0.1327(3) 0.0383(14) Uiso 1.000000 R
C9 C 0.8660(3) 0.7088(5) -0.0241(3) 0.0333(12) Uani 1.000000 .
H9 H 0.8613(3) 0.8009(5) -0.0362(3) 0.0399(14) Uiso 1.000000 R
C10 C 0.8727(3) 0.6717(4) 0.0498(3) 0.0301(11) Uani 1.000000 .
H10 H 0.8738(3) 0.7356(4) 0.0890(3) 0.0361(13) Uiso 1.000000 R
C11 C 0.5941(4) 0.9159(6) 0.1348(3) 0.0475(15) Uani 1.000000 .
H11a H 0.6603(9) 0.876(3) 0.1305(8) 0.071(2) Uiso 1.000000 GR
H11b H 0.5426(18) 0.846(2) 0.1297(8) 0.071(2) Uiso 1.000000 GR
H11c H 0.582(3) 0.9826(8) 0.0954(3) 0.071(2) Uiso 1.000000 GR
C12 C 0.5908(4) 0.9823(5) 0.2108(2) 0.0372(12) Uani 1.000000 .
H12a H 0.6435(4) 1.0516(5) 0.2163(2) 0.0446(15) Uiso 1.000000 R
H12b H 0.5251(4) 1.0266(5) 0.2141(2) 0.0446(15) Uiso 1.000000 R
C13 C 0.6064(4) 0.8826(5) 0.2735(3) 0.0340(12) Uani 1.000000 .
H13a H 0.5506(4) 0.8176(5) 0.2693(3) 0.0408(14) Uiso 1.000000 R
H13b H 0.6691(4) 0.8330(5) 0.2666(3) 0.0408(14) Uiso 1.000000 R
C14 C 0.6125(3) 0.9395(4) 0.3505(2) 0.0242(10) Uani 1.000000 .
C15 C 0.6220(3) 1.0832(4) 0.4460(2) 0.0216(10) Uani 1.000000 .
C16 C 0.6221(3) 0.9538(4) 0.4742(2) 0.0240(10) Uani 1.000000 .
C17 C 0.6276(3) 0.9296(5) 0.5509(3) 0.0307(11) Uani 1.000000 .
H17 H 0.6279(3) 0.8415(5) 0.5703(3) 0.0369(13) Uiso 1.000000 R
C18 C 0.6325(3) 1.0387(5) 0.5972(2) 0.0306(11) Uani 1.000000 .
H18 H 0.6363(3) 1.0260(5) 0.6499(2) 0.0368(13) Uiso 1.000000 R
C19 C 0.6319(3) 1.1693(5) 0.5680(2) 0.0295(11) Uani 1.000000 .
H19 H 0.6347(3) 1.2425(5) 0.6018(2) 0.0354(13) Uiso 1.000000 R
C20 C 0.6273(3) 1.1948(4) 0.4917(2) 0.0253(10) Uani 1.000000 .
H20 H 0.6278(3) 1.2828(4) 0.4721(2) 0.0303(12) Uiso 1.000000 R
Cl1 Cl 0.68072(11) 0.31483(12) 0.27659(6) 0.0407(3) Uani 1.000000 .
Cl2 Cl 0.89870(10) 0.39616(14) 0.41347(7) 0.0476(4) Uani 1.000000 .
Cl3 Cl 0.64906(10) 0.55929(11) 0.42570(7) 0.0380(3) Uani 1.000000 .
Cl4 Cl 0.81548(9) 0.63129(10) 0.26699(6) 0.0267(3) Uani 1.000000 .
N1 N 0.8875(3) 0.3181(3) 0.04121(18) 0.0221(8) Uani 1.000000 .
H1 H 0.8901(3) 0.2414(3) 0.01755(18) 0.0265(10) Uiso 1.000000 R
N2 N 0.8858(3) 0.4627(3) 0.13044(18) 0.0248(8) Uani 1.000000 .
H2 H 0.8867(3) 0.4976(3) 0.17556(18) 0.0298(10) Uiso 1.000000 R
N3 N 0.6160(3) 1.0688(3) 0.36827(19) 0.0236(8) Uani 1.000000 .
H3 H 0.6147(3) 1.1349(3) 0.33592(19) 0.0283(10) Uiso 1.000000 R
N4 N 0.6155(3) 0.8684(4) 0.4131(2) 0.0283(9) Uani 1.000000 .
H4 H 0.6136(3) 0.7808(4) 0.4155(2) 0.0339(11) Uiso 1.000000 R
Zn1 Zn 0.76085(4) 0.47621(5) 0.34865(3) 0.02339(15) Uani 1.000000 .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cl 0.14873 0.16029 11.46040 7.19640 6.25560 1.64550 0.01040 1.16620 18.51940
47.77840 -9.55739974976
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Zn 0.31207 1.46666 14.07430 7.03180 5.16520 2.41000 3.26550 0.23330 10.31630
58.70970 1.30410003662
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
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 126.7(4) . .
N2 C1 C2 125.8(4) . .
N2 C1 N1 107.4(4) . .
H2a C2 C1 108.4(3) . .
H2b C2 C1 108.4(3) . .
H2b C2 H2a 107.5 . .
C3 C2 C1 115.5(4) . .
C3 C2 H2a 108.4(3) . .
C3 C2 H2b 108.4(3) . .
H3a C3 C2 109.4(3) . .
H3b C3 C2 109.4(3) . .
H3b C3 H3a 108.0 . .
C4 C3 C2 111.2(4) . .
C4 C3 H3a 109.4(3) . .
C4 C3 H3b 109.4(3) . .
H4a C4 C3 109.5 . .
H4b C4 C3 109.5 . .
H4b C4 H4a 109.5 . .
H4c C4 C3 109.5 . .
H4c C4 H4a 109.5 . .
H4c C4 H4b 109.5 . .
C10 C5 C6 121.5(4) . .
N2 C5 C6 106.1(4) . .
N2 C5 C10 132.3(4) . .
C7 C6 C5 122.1(4) . .
N1 C6 C5 105.9(3) . .
N1 C6 C7 132.0(4) . .
H7 C7 C6 121.9(3) . .
C8 C7 C6 116.1(4) . .
C8 C7 H7 121.9(3) . .
H8 C8 C7 119.2(3) . .
C9 C8 C7 121.6(4) . .
C9 C8 H8 119.2(3) . .
H9 C9 C8 118.9(3) . .
C10 C9 C8 122.2(4) . .
C10 C9 H9 118.9(3) . .
C9 C10 C5 116.4(4) . .
H10 C10 C5 121.8(3) . .
H10 C10 C9 121.8(3) . .
H11b C11 H11a 109.5 . .
H11c C11 H11a 109.5 . .
H11c C11 H11b 109.5 . .
C12 C11 H11a 109.5 . .
C12 C11 H11b 109.5 . .
C12 C11 H11c 109.5 . .
H12a C12 C11 109.3(3) . .
H12b C12 C11 109.3(3) . .
H12b C12 H12a 108.0 . .
C13 C12 C11 111.4(4) . .
C13 C12 H12a 109.3(3) . .
C13 C12 H12b 109.3(3) . .
H13a C13 C12 108.4(3) . .
H13b C13 C12 108.4(3) . .
H13b C13 H13a 107.5 . .
C14 C13 C12 115.5(4) . .
C14 C13 H13a 108.4(3) . .
C14 C13 H13b 108.4(3) . .
N3 C14 C13 126.3(4) . .
N4 C14 C13 125.0(4) . .
N4 C14 N3 108.7(4) . .
C20 C15 C16 122.6(4) . .
N3 C15 C16 105.3(4) . .
N3 C15 C20 132.0(4) . .
C17 C16 C15 121.2(4) . .
N4 C16 C15 106.9(4) . .
N4 C16 C17 131.8(4) . .
H17 C17 C16 121.4(3) . .
C18 C17 C16 117.1(4) . .
C18 C17 H17 121.4(3) . .
H18 C18 C17 119.4(3) . .
C19 C18 C17 121.1(4) . .
C19 C18 H18 119.4(3) . .
H19 C19 C18 118.8(3) . .
C20 C19 C18 122.3(4) . .
C20 C19 H19 118.8(3) . .
C19 C20 C15 115.5(4) . .
H20 C20 C15 122.2(2) . .
H20 C20 C19 122.2(3) . .
C6 N1 C1 110.3(3) . .
H1 N1 C1 124.9(2) . .
H1 N1 C6 124.9(2) . .
C5 N2 C1 110.3(3) . .
H2 N2 C1 124.9(2) . .
H2 N2 C5 124.9(2) . .
C15 N3 C14 109.7(3) . .
H3 N3 C14 125.2(2) . .
H3 N3 C15 125.2(2) . .
C16 N4 C14 109.4(4) . .
H4 N4 C14 125.3(2) . .
H4 N4 C16 125.3(2) . .
Cl2 Zn1 Cl1 111.85(6) . .
Cl3 Zn1 Cl1 107.53(5) . .
Cl3 Zn1 Cl2 111.56(5) . .
Cl4 Zn1 Cl1 106.12(4) . .
Cl4 Zn1 Cl2 106.58(5) . .
Cl4 Zn1 Cl3 113.13(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.472(6) .
C1 N1 1.341(5) .
C1 N2 1.338(5) .
C2 H2a 0.9900 .
C2 H2b 0.9900 .
C2 C3 1.516(6) .
C3 H3a 0.9900 .
C3 H3b 0.9900 .
C3 C4 1.523(6) .
C4 H4a 0.9800 .
C4 H4b 0.9800 .
C4 H4c 0.9800 .
C5 C6 1.394(6) .
C5 C10 1.396(6) .
C5 N2 1.386(5) .
C6 C7 1.390(6) .
C6 N1 1.388(5) .
C7 H7 0.9500 .
C7 C8 1.388(6) .
C8 H8 0.9500 .
C8 C9 1.405(7) .
C9 H9 0.9500 .
C9 C10 1.372(6) .
C10 H10 0.9500 .
C11 H11a 0.9800 .
C11 H11b 0.9800 .
C11 H11c 0.9800 .
C11 C12 1.519(6) .
C12 H12a 0.9900 .
C12 H12b 0.9900 .
C12 C13 1.507(7) .
C13 H13a 0.9900 .
C13 H13b 0.9900 .
C13 C14 1.489(6) .
C14 N3 1.336(5) .
C14 N4 1.327(5) .
C15 C16 1.393(6) .
C15 C20 1.386(6) .
C15 N3 1.396(5) .
C16 C17 1.393(6) .
C16 N4 1.387(5) .
C17 H17 0.9500 .
C17 C18 1.372(7) .
C18 H18 0.9500 .
C18 C19 1.411(6) .
C19 H19 0.9500 .
C19 C20 1.388(6) .
C20 H20 0.9500 .
Cl1 Zn1 2.2899(12) .
Cl2 Zn1 2.2571(14) .
Cl3 Zn1 2.2622(13) .
Cl4 Zn1 2.2891(11) .
N1 H1 0.8800 .
N2 H2 0.8800 .
N3 H3 0.8800 .
N4 H4 0.8800 .
