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#$Date: 2022-05-17 11:58:31 +0300 (Tue, 17 May 2022) $
#$Revision: 275484 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/52/8105281.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_8105281
loop_
_publ_author_name
'Cai, Bin'
'Fu, Chun-Yan'
'Guo, Xin-Yu'
'Wang, Ying'
_publ_section_title
;
 The crystal structure of
 1,3-bis(4-(methoxycarbonyl)benzyl)-2-methyl-1H-benzo[d]imidazol-3-ium
 bromide, C26H25BrN2O4
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              765
_journal_page_last               766
_journal_paper_doi               10.1515/ncrs-2019-0616
_journal_volume                  235
_journal_year                    2020
_chemical_formula_moiety         'C26 H25 N2 O4, Br'
_chemical_formula_sum            'C26 H25 Br N2 O4'
_chemical_formula_weight         509.39
_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
_atom_sites_solution_primary     dual
_cell_angle_alpha                106.775(3)
_cell_angle_beta                 92.534(3)
_cell_angle_gamma                117.424(3)
_cell_formula_units_Z            2
_cell_length_a                   9.4202(5)
_cell_length_b                   9.7871(5)
_cell_length_c                   15.0135(9)
_cell_measurement_reflns_used    7658
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.26
_cell_measurement_theta_min      2.50
_cell_volume                     1150.52(12)
_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 0.999
_diffrn_measured_fraction_theta_max 0.996
_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           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0558
_diffrn_reflns_av_unetI/netI     0.0425
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            22877
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.445
_diffrn_reflns_theta_min         2.414
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.822
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6178
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0843 before and 0.0548 after correction.
The Ratio of minimum to maximum transmission is 0.8288.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_description       needle
_exptl_crystal_F_000             524
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.507
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       0.0043(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     302
_refine_ls_number_reflns         4722
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0316
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0213P)²+0.6778P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0625
_refine_ls_wR_factor_ref         0.0671
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3913
_reflns_number_total             4722
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2019-0616_suppl.cif
_cod_data_source_block           1
_cod_original_cell_volume        1150.52(11)
_cod_database_code               8105281
_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   0.839
_shelx_estimated_absorpt_t_min   0.659
_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:
 C9(H9A,H9B), C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C11(H11), C12(H12), C15(H15), C16(H16),
 C19(H19), C20(H20), C22(H22), C23(H23)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C25(H25A,H25B,H25C), C26(H26A,H26B,H26C)
;
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 0.39309(3) 0.71322(3) 0.02283(2) 0.02496(8) Uani 1 1 d . . . . .
C1 C 0.1072(3) 0.1218(2) 0.12137(14) 0.0187(4) Uani 1 1 d . . . . .
C2 C 0.1948(3) 0.0379(3) 0.10799(15) 0.0235(5) Uani 1 1 d . . . . .
H2 H 0.306767 0.089780 0.104177 0.028 Uiso 1 1 calc R . . . .
C3 C 0.1099(3) -0.1247(3) 0.10059(15) 0.0257(5) Uani 1 1 d . . . . .
H3 H 0.165067 -0.186495 0.091939 0.031 Uiso 1 1 calc R . . . .
C4 C -0.0551(3) -0.2009(3) 0.10548(15) 0.0243(5) Uani 1 1 d . . . . .
H4 H -0.109411 -0.313483 0.099410 0.029 Uiso 1 1 calc R . . . .
C5 C -0.1419(3) -0.1170(2) 0.11894(15) 0.0205(4) Uani 1 1 d . . . . .
H5 H -0.254238 -0.169101 0.121993 0.025 Uiso 1 1 calc R . . . .
C6 C -0.0560(2) 0.0470(2) 0.12769(14) 0.0174(4) Uani 1 1 d . . . . .
C7 C 0.0236(3) 0.3049(3) 0.13856(14) 0.0203(4) Uani 1 1 d . . . . .
C8 C 0.0222(3) 0.4589(3) 0.14653(16) 0.0274(5) Uani 1 1 d . . . . .
H8A H 0.046283 0.525499 0.213818 0.041 Uiso 1 1 calc GR . . . .
H8B H -0.085767 0.432281 0.115859 0.041 Uiso 1 1 calc GR . . . .
H8C H 0.105323 0.520666 0.115185 0.041 Uiso 1 1 calc GR . . . .
C9 C 0.3156(3) 0.3995(3) 0.12139(16) 0.0261(5) Uani 1 1 d . . . . .
H9A H 0.307142 0.482360 0.099641 0.031 Uiso 1 1 calc R . . . .
H9B H 0.354978 0.340718 0.072769 0.031 Uiso 1 1 calc R . . . .
C10 C 0.4394(3) 0.4866(2) 0.21385(15) 0.0210(5) Uani 1 1 d . . . . .
C11 C 0.3998(3) 0.5025(3) 0.30261(16) 0.0281(5) Uani 1 1 d . . . . .
H11 H 0.288188 0.453987 0.307343 0.034 Uiso 1 1 calc R . . . .
C12 C 0.5210(3) 0.5885(3) 0.38467(16) 0.0274(5) Uani 1 1 d . . . . .
H12 H 0.492320 0.598189 0.445161 0.033 Uiso 1 1 calc R . . . .
C13 C 0.6839(3) 0.6601(3) 0.37835(15) 0.0223(5) Uani 1 1 d . . . . .
C14 C 0.8211(3) 0.7525(3) 0.46280(16) 0.0272(5) Uani 1 1 d . . . . .
C15 C 0.7243(3) 0.6456(3) 0.28950(16) 0.0261(5) Uani 1 1 d . . . . .
H15 H 0.835935 0.695530 0.284935 0.031 Uiso 1 1 calc R . . . .
C16 C 0.6036(3) 0.5593(3) 0.20780(16) 0.0250(5) Uani 1 1 d . . . . .
H16 H 0.632508 0.549431 0.147356 0.030 Uiso 1 1 calc R . . . .
C17 C -0.2665(3) 0.1412(3) 0.15632(15) 0.0218(5) Uani 1 1 d . . . . .
H17A H -0.352812 0.029976 0.115132 0.026 Uiso 1 1 calc R . . . .
H17B H -0.287221 0.222485 0.140107 0.026 Uiso 1 1 calc R . . . .
C18 C -0.2724(3) 0.1611(3) 0.25980(15) 0.0210(5) Uani 1 1 d . . . . .
C19 C -0.3324(3) 0.0252(3) 0.28832(16) 0.0246(5) Uani 1 1 d . . . . .
H19 H -0.378555 -0.081781 0.241973 0.030 Uiso 1 1 calc R . . . .
C20 C -0.3254(3) 0.0442(3) 0.38340(16) 0.0262(5) Uani 1 1 d . . . . .
H20 H -0.365377 -0.049470 0.402176 0.031 Uiso 1 1 calc R . . . .
C21 C -0.2600(3) 0.2003(3) 0.45202(16) 0.0259(5) Uani 1 1 d . . . . .
C22 C -0.2056(3) 0.3353(3) 0.42323(18) 0.0358(6) Uani 1 1 d . . . . .
H22 H -0.164047 0.441865 0.469264 0.043 Uiso 1 1 calc R . . . .
C23 C -0.2114(3) 0.3160(3) 0.32841(17) 0.0335(6) Uani 1 1 d . . . . .
H23 H -0.173291 0.409586 0.309610 0.040 Uiso 1 1 calc R . . . .
C24 C -0.2381(3) 0.2271(3) 0.55538(17) 0.0306(5) Uani 1 1 d . . . . .
C25 C -0.2742(3) 0.1033(4) 0.67171(18) 0.0413(7) Uani 1 1 d . . . . .
H25A H -0.156434 0.152491 0.694777 0.062 Uiso 1 1 calc GR . . . .
H25B H -0.331708 -0.005105 0.677915 0.062 Uiso 1 1 calc GR . . . .
H25C H -0.313128 0.174084 0.709422 0.062 Uiso 1 1 calc GR . . . .
C26 C 0.9006(3) 0.8440(3) 0.62869(17) 0.0407(7) Uani 1 1 d . . . . .
H26A H 0.959964 0.783925 0.628464 0.061 Uiso 1 1 calc GR . . . .
H26B H 0.853934 0.853249 0.685750 0.061 Uiso 1 1 calc GR . . . .
H26C H 0.975971 0.954040 0.628629 0.061 Uiso 1 1 calc GR . . . .
N1 N 0.1527(2) 0.2819(2) 0.12819(12) 0.0199(4) Uani 1 1 d . . . . .
N2 N -0.1038(2) 0.1657(2) 0.13919(12) 0.0173(4) Uani 1 1 d . . . . .
O1 O 0.77036(19) 0.7564(2) 0.54478(11) 0.0319(4) Uani 1 1 d . . . . .
O2 O 0.9624(2) 0.8150(3) 0.45785(13) 0.0473(5) Uani 1 1 d . . . . .
O3 O -0.1664(2) 0.3611(2) 0.61727(12) 0.0447(5) Uani 1 1 d . . . . .
O4 O -0.3057(2) 0.0864(2) 0.57299(11) 0.0331(4) 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'
O O 0.0106 0.0060 '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'
Br Br -0.2901 2.4595 '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
C6 C1 C2 122.15(19) . .
C6 C1 N1 106.78(18) . .
N1 C1 C2 131.0(2) . .
C1 C2 H2 121.9 . .
C3 C2 C1 116.3(2) . .
C3 C2 H2 121.9 . .
C2 C3 H3 119.2 . .
C2 C3 C4 121.7(2) . .
C4 C3 H3 119.2 . .
C3 C4 H4 119.1 . .
C5 C4 C3 121.9(2) . .
C5 C4 H4 119.1 . .
C4 C5 H5 121.8 . .
C4 C5 C6 116.4(2) . .
C6 C5 H5 121.8 . .
C1 C6 N2 106.42(17) . .
C5 C6 C1 121.57(19) . .
C5 C6 N2 131.95(19) . .
N1 C7 C8 125.26(19) . .
N2 C7 C8 125.7(2) . .
N2 C7 N1 109.02(18) . .
C7 C8 H8A 109.5 . .
C7 C8 H8B 109.5 . .
C7 C8 H8C 109.5 . .
H8A C8 H8B 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
H9A C9 H9B 107.7 . .
C10 C9 H9A 108.8 . .
C10 C9 H9B 108.8 . .
N1 C9 H9A 108.8 . .
N1 C9 H9B 108.8 . .
N1 C9 C10 113.58(18) . .
C11 C10 C9 124.3(2) . .
C11 C10 C16 119.1(2) . .
C16 C10 C9 116.64(19) . .
C10 C11 H11 119.6 . .
C10 C11 C12 120.8(2) . .
C12 C11 H11 119.6 . .
C11 C12 H12 120.0 . .
C13 C12 C11 119.9(2) . .
C13 C12 H12 120.0 . .
C12 C13 C14 123.2(2) . .
C12 C13 C15 119.5(2) . .
C15 C13 C14 117.3(2) . .
O1 C14 C13 112.94(19) . .
O2 C14 C13 123.6(2) . .
O2 C14 O1 123.5(2) . .
C13 C15 H15 119.7 . .
C16 C15 C13 120.6(2) . .
C16 C15 H15 119.7 . .
C10 C16 H16 120.0 . .
C15 C16 C10 120.1(2) . .
C15 C16 H16 120.0 . .
H17A C17 H17B 108.2 . .
C18 C17 H17A 109.7 . .
C18 C17 H17B 109.7 . .
N2 C17 H17A 109.7 . .
N2 C17 H17B 109.7 . .
N2 C17 C18 109.94(17) . .
C19 C18 C17 120.44(19) . .
C19 C18 C23 118.8(2) . .
C23 C18 C17 120.7(2) . .
C18 C19 H19 119.7 . .
C20 C19 C18 120.6(2) . .
C20 C19 H19 119.7 . .
C19 C20 H20 119.8 . .
C19 C20 C21 120.3(2) . .
C21 C20 H20 119.8 . .
C20 C21 C24 121.9(2) . .
C22 C21 C20 119.1(2) . .
C22 C21 C24 118.9(2) . .
C21 C22 H22 119.8 . .
C23 C22 C21 120.4(2) . .
C23 C22 H22 119.8 . .
C18 C23 H23 119.6 . .
C22 C23 C18 120.7(2) . .
C22 C23 H23 119.6 . .
O3 C24 C21 124.1(2) . .
O3 C24 O4 123.3(2) . .
O4 C24 C21 112.6(2) . .
H25A C25 H25B 109.5 . .
H25A C25 H25C 109.5 . .
H25B C25 H25C 109.5 . .
O4 C25 H25A 109.5 . .
O4 C25 H25B 109.5 . .
O4 C25 H25C 109.5 . .
H26A C26 H26B 109.5 . .
H26A C26 H26C 109.5 . .
H26B C26 H26C 109.5 . .
O1 C26 H26A 109.5 . .
O1 C26 H26B 109.5 . .
O1 C26 H26C 109.5 . .
C1 N1 C9 123.48(18) . .
C7 N1 C1 108.94(17) . .
C7 N1 C9 127.55(18) . .
C6 N2 C17 124.25(17) . .
C7 N2 C6 108.84(17) . .
C7 N2 C17 126.76(17) . .
C14 O1 C26 114.58(19) . .
C24 O4 C25 115.3(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.392(3) .
C1 C6 1.388(3) .
C1 N1 1.391(3) .
C2 H2 0.9500 .
C2 C3 1.379(3) .
C3 H3 0.9500 .
C3 C4 1.397(3) .
C4 H4 0.9500 .
C4 C5 1.386(3) .
C5 H5 0.9500 .
C5 C6 1.386(3) .
C6 N2 1.399(3) .
C7 C8 1.484(3) .
C7 N1 1.342(3) .
C7 N2 1.341(3) .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
C9 H9A 0.9900 .
C9 H9B 0.9900 .
C9 C10 1.507(3) .
C9 N1 1.464(3) .
C10 C11 1.384(3) .
C10 C16 1.394(3) .
C11 H11 0.9500 .
C11 C12 1.386(3) .
C12 H12 0.9500 .
C12 C13 1.384(3) .
C13 C14 1.487(3) .
C13 C15 1.389(3) .
C14 O1 1.337(3) .
C14 O2 1.199(3) .
C15 H15 0.9500 .
C15 C16 1.380(3) .
C16 H16 0.9500 .
C17 H17A 0.9900 .
C17 H17B 0.9900 .
C17 C18 1.516(3) .
C17 N2 1.485(3) .
C18 C19 1.389(3) .
C18 C23 1.391(3) .
C19 H19 0.9500 .
C19 C20 1.380(3) .
C20 H20 0.9500 .
C20 C21 1.394(3) .
C21 C22 1.386(3) .
C21 C24 1.485(3) .
C22 H22 0.9500 .
C22 C23 1.376(3) .
C23 H23 0.9500 .
C24 O3 1.210(3) .
C24 O4 1.338(3) .
C25 H25A 0.9800 .
C25 H25B 0.9800 .
C25 H25C 0.9800 .
C25 O4 1.444(3) .
C26 H26A 0.9800 .
C26 H26B 0.9800 .
C26 H26C 0.9800 .
C26 O1 1.449(3) .
