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#$Date: 2023-06-16 10:41:06 +0300 (Fri, 16 Jun 2023) $
#$Revision: 284488 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/73/8107382.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_8107382
loop_
_publ_author_name
'Yu Wen, Ya-Huan'
'Zhang, Pin'
'Liu, Bin'
_publ_section_title
;
 Crystal structure of
 1-(3-bromopropyl)-2-((4-chlorophenoxy)methyl)-4-methyl-1H-benzo[d]imidazole,
 C18H18BrClN2O
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              163
_journal_page_last               164
_journal_paper_doi               10.1515/ncrs-2022-0470
_journal_volume                  238
_journal_year                    2023
_chemical_formula_moiety         'C18 H18 Br Cl N2 O'
_chemical_formula_sum            'C18 H18 Br Cl N2 O'
_chemical_formula_weight         393.70
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                83.1120(10)
_cell_angle_beta                 72.2590(10)
_cell_angle_gamma                73.9400(10)
_cell_formula_units_Z            2
_cell_length_a                   9.0583(4)
_cell_length_b                   9.2694(4)
_cell_length_c                   11.1183(4)
_cell_measurement_reflns_used    4256
_cell_measurement_temperature    170
_cell_measurement_theta_max      26.34
_cell_measurement_theta_min      2.64
_cell_volume                     853.80(6)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019) [1]'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019) [1]'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009) [2]'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009) [2]'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015) [3]'
_computing_structure_solution    'ShelXT (Sheldrick, 2015) [4]'
_diffrn_ambient_temperature      170.00
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_av_unetI/netI     0.0457
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_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            9844
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.424
_diffrn_reflns_theta_min         1.925
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.569
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.4898
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1029 before and 0.0504 after correction.
The Ratio of minimum to maximum transmission is 0.6571.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.531
_exptl_crystal_description       block
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.573
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3459
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0381
_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)+(0.0310P)²+0.7828P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0854
_refine_ls_wR_factor_ref         0.0969
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2773
_reflns_number_total             3459
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2022-0470_suppl.cif
_cod_data_source_block           mo_2
_cod_database_code               8107382
_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   0.904
_shelx_estimated_absorpt_t_min   0.765
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C12(H12), C13(H13), C14(H14)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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
Br1 Br 0.61078(4) 0.55172(5) 0.10896(3) 0.05187(14) Uani 1 1 d . . . . .
C1 C 0.1994(3) 0.6215(3) 0.2755(3) 0.0303(6) Uani 1 1 d . . . . .
H1 H 0.257848 0.528796 0.303693 0.036 Uiso 1 1 calc R U . . .
C2 C 0.1271(3) 0.6241(3) 0.1823(3) 0.0325(6) Uani 1 1 d . . . . .
H2 H 0.135570 0.533453 0.145948 0.039 Uiso 1 1 calc R U . . .
C3 C 0.0421(3) 0.7598(3) 0.1424(3) 0.0288(6) Uani 1 1 d . . . . .
C4 C 0.0254(3) 0.8915(3) 0.1956(3) 0.0321(6) Uani 1 1 d . . . . .
H4 H -0.036097 0.983610 0.169096 0.038 Uiso 1 1 calc R U . . .
C5 C 0.0993(3) 0.8888(3) 0.2890(3) 0.0298(6) Uani 1 1 d . . . . .
H5 H 0.089663 0.979493 0.325869 0.036 Uiso 1 1 calc R U . . .
C6 C 0.1869(3) 0.7540(3) 0.3278(3) 0.0256(6) Uani 1 1 d . . . . .
C7 C 0.2776(3) 0.8750(3) 0.4593(3) 0.0309(6) Uani 1 1 d . . . . .
H7A H 0.172101 0.927908 0.513871 0.037 Uiso 1 1 calc R U . . .
H7B H 0.309691 0.942020 0.385231 0.037 Uiso 1 1 calc R U . . .
C8 C 0.3985(3) 0.8382(3) 0.5309(3) 0.0267(6) Uani 1 1 d . . . . .
C9 C 0.5131(3) 0.8247(3) 0.6751(2) 0.0272(6) Uani 1 1 d . . . . .
C10 C 0.5479(4) 0.8320(3) 0.7890(3) 0.0342(7) Uani 1 1 d . . . . .
C11 C 0.4152(4) 0.8807(4) 0.9075(3) 0.0483(9) Uani 1 1 d . . . . .
H11A H 0.354327 0.983649 0.894534 0.072 Uiso 1 1 calc R U . . .
H11B H 0.461060 0.876771 0.977482 0.072 Uiso 1 1 calc R U . . .
H11C H 0.343752 0.813313 0.927833 0.072 Uiso 1 1 calc R U . . .
C12 C 0.7087(4) 0.7907(3) 0.7834(3) 0.0371(7) Uani 1 1 d . . . . .
H12 H 0.737855 0.794519 0.857890 0.045 Uiso 1 1 calc R U . . .
C13 C 0.8303(4) 0.7435(3) 0.6722(3) 0.0384(8) Uani 1 1 d . . . . .
H13 H 0.938889 0.717236 0.673529 0.046 Uiso 1 1 calc R U . . .
C14 C 0.7967(3) 0.7340(3) 0.5610(3) 0.0331(7) Uani 1 1 d . . . . .
H14 H 0.878849 0.701154 0.485787 0.040 Uiso 1 1 calc R U . . .
C15 C 0.6352(3) 0.7756(3) 0.5654(3) 0.0280(6) Uani 1 1 d . . . . .
C16 C 0.6358(4) 0.7271(3) 0.3463(3) 0.0328(7) Uani 1 1 d . . . . .
H16A H 0.739904 0.753309 0.311051 0.039 Uiso 1 1 calc R U . . .
H16B H 0.567238 0.774645 0.290704 0.039 Uiso 1 1 calc R U . . .
C17 C 0.6627(4) 0.5570(3) 0.3501(3) 0.0362(7) Uani 1 1 d . . . . .
H17A H 0.728859 0.511290 0.407900 0.043 Uiso 1 1 calc R U . . .
H17B H 0.557804 0.532544 0.385728 0.043 Uiso 1 1 calc R U . . .
C18 C 0.7436(4) 0.4867(4) 0.2233(3) 0.0383(7) Uani 1 1 d . . . . .
H18A H 0.767282 0.375947 0.235285 0.046 Uiso 1 1 calc R U . . .
H18B H 0.846586 0.514233 0.185190 0.046 Uiso 1 1 calc R U . . .
Cl1 Cl -0.04600(10) 0.76262(9) 0.02227(7) 0.0427(2) Uani 1 1 d . . . . .
N1 N 0.5592(3) 0.7838(3) 0.4732(2) 0.0268(5) Uani 1 1 d . . . . .
N2 N 0.3646(3) 0.8642(3) 0.6506(2) 0.0288(5) Uani 1 1 d . . . . .
O1 O 0.2661(2) 0.7387(2) 0.41824(19) 0.0325(5) 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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
C2 C1 H1 120.0 . .
C2 C1 C6 120.0(3) . .
C6 C1 H1 120.0 . .
C1 C2 H2 120.3 . .
C1 C2 C3 119.4(3) . .
C3 C2 H2 120.3 . .
C2 C3 Cl1 119.2(2) . .
C4 C3 C2 121.2(3) . .
C4 C3 Cl1 119.6(2) . .
C3 C4 H4 120.4 . .
C3 C4 C5 119.3(3) . .
C5 C4 H4 120.4 . .
C4 C5 H5 120.1 . .
C6 C5 C4 119.9(3) . .
C6 C5 H5 120.1 . .
C5 C6 C1 120.2(3) . .
O1 C6 C1 115.1(2) . .
O1 C6 C5 124.7(3) . .
H7A C7 H7B 108.3 . .
C8 C7 H7A 109.9 . .
C8 C7 H7B 109.9 . .
O1 C7 H7A 109.9 . .
O1 C7 H7B 109.9 . .
O1 C7 C8 109.1(2) . .
N1 C8 C7 122.0(2) . .
N2 C8 C7 123.8(3) . .
N2 C8 N1 114.0(2) . .
C15 C9 C10 121.0(3) . .
N2 C9 C10 128.8(3) . .
N2 C9 C15 110.2(2) . .
C9 C10 C11 120.6(3) . .
C12 C10 C9 115.8(3) . .
C12 C10 C11 123.6(3) . .
C10 C11 H11A 109.5 . .
C10 C11 H11B 109.5 . .
C10 C11 H11C 109.5 . .
H11A C11 H11B 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
C10 C12 H12 118.7 . .
C10 C12 C13 122.6(3) . .
C13 C12 H12 118.7 . .
C12 C13 H13 119.1 . .
C14 C13 C12 121.8(3) . .
C14 C13 H13 119.1 . .
C13 C14 H14 122.0 . .
C13 C14 C15 116.1(3) . .
C15 C14 H14 122.0 . .
C14 C15 C9 122.7(3) . .
N1 C15 C9 105.6(2) . .
N1 C15 C14 131.8(3) . .
H16A C16 H16B 108.1 . .
C17 C16 H16A 109.6 . .
C17 C16 H16B 109.6 . .
N1 C16 H16A 109.6 . .
N1 C16 H16B 109.6 . .
N1 C16 C17 110.2(2) . .
C16 C17 H17A 108.7 . .
C16 C17 H17B 108.7 . .
H17A C17 H17B 107.6 . .
C18 C17 C16 114.4(2) . .
C18 C17 H17A 108.7 . .
C18 C17 H17B 108.7 . .
Br1 C18 H18A 109.3 . .
Br1 C18 H18B 109.3 . .
C17 C18 Br1 111.8(2) . .
C17 C18 H18A 109.3 . .
C17 C18 H18B 109.3 . .
H18A C18 H18B 107.9 . .
C8 N1 C15 105.9(2) . .
C8 N1 C16 128.1(2) . .
C15 N1 C16 125.5(2) . .
C8 N2 C9 104.3(2) . .
C6 O1 C7 116.4(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C18 1.943(3) .
C1 H1 0.9500 .
C1 C2 1.379(4) .
C1 C6 1.383(4) .
C2 H2 0.9500 .
C2 C3 1.382(4) .
C3 C4 1.372(4) .
C3 Cl1 1.746(3) .
C4 H4 0.9500 .
C4 C5 1.391(4) .
C5 H5 0.9500 .
C5 C6 1.382(4) .
C6 O1 1.376(3) .
C7 H7A 0.9900 .
C7 H7B 0.9900 .
C7 C8 1.486(4) .
C7 O1 1.434(3) .
C8 N1 1.374(4) .
C8 N2 1.308(3) .
C9 C10 1.408(4) .
C9 C15 1.397(4) .
C9 N2 1.394(4) .
C10 C11 1.505(4) .
C10 C12 1.383(4) .
C11 H11A 0.9800 .
C11 H11B 0.9800 .
C11 H11C 0.9800 .
C12 H12 0.9500 .
C12 C13 1.403(5) .
C13 H13 0.9500 .
C13 C14 1.378(4) .
C14 H14 0.9500 .
C14 C15 1.393(4) .
C15 N1 1.383(3) .
C16 H16A 0.9900 .
C16 H16B 0.9900 .
C16 C17 1.525(4) .
C16 N1 1.459(4) .
C17 H17A 0.9900 .
C17 H17B 0.9900 .
C17 C18 1.508(4) .
C18 H18A 0.9900 .
C18 H18B 0.9900 .
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 C3 C4 -1.5(4) . . . .
C1 C2 C3 Cl1 178.8(2) . . . .
C1 C6 O1 C7 170.2(2) . . . .
C2 C1 C6 C5 1.3(4) . . . .
C2 C1 C6 O1 -178.9(2) . . . .
C2 C3 C4 C5 1.9(4) . . . .
C3 C4 C5 C6 -0.7(4) . . . .
C4 C5 C6 C1 -0.9(4) . . . .
C4 C5 C6 O1 179.3(3) . . . .
C5 C6 O1 C7 -10.0(4) . . . .
C6 C1 C2 C3 -0.2(4) . . . .
C7 C8 N1 C15 174.8(2) . . . .
C7 C8 N1 C16 -12.6(4) . . . .
C7 C8 N2 C9 -175.1(2) . . . .
C8 C7 O1 C6 -166.1(2) . . . .
C9 C10 C12 C13 -0.4(4) . . . .
C9 C15 N1 C8 0.7(3) . . . .
C9 C15 N1 C16 -172.2(2) . . . .
C10 C9 C15 C14 -1.2(4) . . . .
C10 C9 C15 N1 -179.5(2) . . . .
C10 C9 N2 C8 179.1(3) . . . .
C10 C12 C13 C14 -0.5(4) . . . .
C11 C10 C12 C13 179.0(3) . . . .
C12 C13 C14 C15 0.6(4) . . . .
C13 C14 C15 C9 0.2(4) . . . .
C13 C14 C15 N1 178.1(3) . . . .
C14 C15 N1 C8 -177.4(3) . . . .
C14 C15 N1 C16 9.7(5) . . . .
C15 C9 C10 C11 -178.2(3) . . . .
C15 C9 C10 C12 1.3(4) . . . .
C15 C9 N2 C8 0.4(3) . . . .
C16 C17 C18 Br1 -65.1(3) . . . .
C17 C16 N1 C8 -93.5(3) . . . .
C17 C16 N1 C15 77.8(3) . . . .
Cl1 C3 C4 C5 -178.4(2) . . . .
N1 C8 N2 C9 0.1(3) . . . .
N1 C16 C17 C18 -179.3(3) . . . .
N2 C8 N1 C15 -0.5(3) . . . .
N2 C8 N1 C16 172.2(2) . . . .
N2 C9 C10 C11 3.2(5) . . . .
N2 C9 C10 C12 -177.4(3) . . . .
N2 C9 C15 C14 177.6(2) . . . .
N2 C9 C15 N1 -0.7(3) . . . .
O1 C7 C8 N1 68.9(3) . . . .
O1 C7 C8 N2 -116.3(3) . . . .
