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#$Date: 2022-12-13 10:25:24 +0200 (Tue, 13 Dec 2022) $
#$Revision: 279860 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/63/8106385.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_8106385
loop_
_publ_author_name
'Sheng, Liang-Quan'
_publ_section_title
;
 Crystal structure of
 4,4′-(1,4-phenylene)bis(1H-imidazol-3-ium)bis(2-carboxybenzoate),
 C30H26N4O8
;
_journal_issue                   6
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1023
_journal_page_last               1024
_journal_paper_doi               10.1515/ncrs-2018-0146
_journal_volume                  233
_journal_year                    2018
_chemical_formula_sum            'C30 H26 N4 O8'
_chemical_formula_weight         570.55
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_cell_angle_alpha                90
_cell_angle_beta                 92.765(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.6363(7)
_cell_length_b                   9.0231(9)
_cell_length_c                   22.082(2)
_cell_measurement_reflns_used    1443
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.10
_cell_measurement_theta_min      2.92
_cell_volume                     1320.7(2)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6471
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.917
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_type   'SADABS; Bruker, 2000'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_description       block
_exptl_crystal_F_000             596
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.220
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.955
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2310
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.955
_refine_ls_R_factor_all          0.0699
_refine_ls_R_factor_gt           0.0455
_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)+(0.0627P)²+0.5280P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1103
_refine_ls_wR_factor_ref         0.1234
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1664
_reflns_number_total             2310
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2018-0146_suppl.cif
_cod_data_source_block           B
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               8106385
_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_min   0.974
_shelx_estimated_absorpt_t_max   0.977
loop_
_space_group_symop_operation_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 -0.2627(4) 0.4076(3) 0.29001(12) 0.0540(7) Uani 1 1 d . . . . .
H1A H -0.348507 0.322246 0.285404 0.081 Uiso 1 1 calc R U . . .
H1B H -0.336858 0.494691 0.277660 0.081 Uiso 1 1 calc R U . . .
H1C H -0.216756 0.417168 0.331717 0.081 Uiso 1 1 calc R U . . .
C2 C -0.0847(3) 0.3897(3) 0.25135(10) 0.0402(6) Uani 1 1 d . . . . .
C3 C 0.0631(3) 0.2869(3) 0.26601(11) 0.0485(6) Uani 1 1 d . . . . .
H3 H 0.053044 0.228363 0.300389 0.058 Uiso 1 1 calc R U . . .
C4 C 0.2260(3) 0.2701(3) 0.23010(11) 0.0466(6) Uani 1 1 d . . . . .
H4 H 0.321886 0.198302 0.240604 0.056 Uiso 1 1 calc R U . . .
C5 C 0.2527(3) 0.3563(2) 0.17876(10) 0.0366(5) Uani 1 1 d . . . . .
C6 C 0.1025(3) 0.4622(2) 0.16302(10) 0.0353(5) Uani 1 1 d . . . . .
C7 C -0.0619(3) 0.4741(2) 0.19960(10) 0.0392(5) Uani 1 1 d . . . . .
H7 H -0.162115 0.542429 0.188724 0.047 Uiso 1 1 calc R U . . .
C8 C 0.0945(4) 0.5663(3) 0.10941(11) 0.0438(6) Uani 1 1 d . . . . .
C9 C 0.4410(3) 0.3189(3) 0.14589(11) 0.0424(6) Uani 1 1 d . . . . .
C10 C 0.4133(3) -0.0578(2) 0.04994(10) 0.0392(5) Uani 1 1 d . . . . .
H10 H 0.355484 -0.097786 0.083839 0.047 Uiso 1 1 calc R U . . .
C11 C 0.3224(3) 0.0623(2) 0.02077(9) 0.0311(5) Uani 1 1 d . . . . .
C12 C 0.4120(3) 0.1194(2) -0.02970(10) 0.0386(6) Uani 1 1 d . . . . .
H12 H 0.353701 0.200054 -0.050076 0.046 Uiso 1 1 calc R U . . .
C13 C 0.1355(3) 0.1243(2) 0.04295(9) 0.0323(5) Uani 1 1 d . . . . .
C14 C 0.0330(3) 0.0930(3) 0.09295(10) 0.0400(6) Uani 1 1 d . . . . .
H14 H 0.069535 0.023308 0.122493 0.048 Uiso 1 1 calc R U . . .
C15 C -0.1350(3) 0.2652(3) 0.04348(10) 0.0396(6) Uani 1 1 d . . . . .
H15 H -0.232934 0.335024 0.032212 0.048 Uiso 1 1 calc R U . . .
N1 N 0.0256(2) 0.23360(19) 0.01276(8) 0.0384(5) Uani 1 1 d . . . . .
H1D H 0.047638 0.274144 -0.024163 0.046 Uiso 1 1 d R U . . .
N2 N -0.1346(3) 0.1828(2) 0.09228(8) 0.0404(5) Uani 1 1 d . . . . .
H2A H -0.243234 0.189637 0.122182 0.049 Uiso 1 1 d R U . . .
O1 O 0.2445(3) 0.5781(2) 0.07602(9) 0.0763(7) Uani 1 1 d . . . . .
O2 O -0.0588(3) 0.6400(2) 0.09838(9) 0.0708(6) Uani 1 1 d . . . . .
O3 O 0.4922(3) 0.3959(2) 0.10041(9) 0.0666(6) Uani 1 1 d . . . . .
H3A H 0.377273 0.490218 0.092488 0.080 Uiso 1 1 d R U . . .
O4 O 0.5442(2) 0.2134(2) 0.16348(8) 0.0583(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'
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 H1A 109.5 . .
C2 C1 H1B 109.5 . .
H1A C1 H1B 109.5 . .
C2 C1 H1C 109.5 . .
H1A C1 H1C 109.5 . .
H1B C1 H1C 109.5 . .
C3 C2 C7 117.3(2) . .
C3 C2 C1 120.7(2) . .
C7 C2 C1 122.0(2) . .
C2 C3 C4 120.5(2) . .
C2 C3 H3 119.7 . .
C4 C3 H3 119.7 . .
C3 C4 C5 122.7(2) . .
C3 C4 H4 118.6 . .
C5 C4 H4 118.6 . .
C4 C5 C6 117.50(19) . .
C4 C5 C9 114.00(19) . .
C6 C5 C9 128.5(2) . .
C7 C6 C5 118.2(2) . .
C7 C6 C8 114.04(19) . .
C5 C6 C8 127.73(19) . .
C2 C7 C6 123.7(2) . .
C2 C7 H7 118.1 . .
C6 C7 H7 118.1 . .
O2 C8 O1 120.2(2) . .
O2 C8 C6 119.3(2) . .
O1 C8 C6 120.5(2) . .
O4 C9 O3 120.3(2) . .
O4 C9 C5 118.9(2) . .
O3 C9 C5 120.8(2) . .
C12 C10 C11 121.2(2) 3_655 .
C12 C10 H10 119.4 3_655 .
C11 C10 H10 119.4 . .
C10 C11 C12 118.07(18) . .
C10 C11 C13 120.02(19) . .
C12 C11 C13 121.91(19) . .
C10 C12 C11 120.7(2) 3_655 .
C10 C12 H12 119.7 3_655 .
C11 C12 H12 119.7 . .
C14 C13 N1 105.57(18) . .
C14 C13 C11 131.2(2) . .
N1 C13 C11 123.22(19) . .
C13 C14 N2 107.8(2) . .
C13 C14 H14 126.1 . .
N2 C14 H14 126.1 . .
N2 C15 N1 109.24(19) . .
N2 C15 H15 125.4 . .
N1 C15 H15 125.4 . .
C15 N1 C13 109.10(18) . .
C15 N1 H1D 122.7 . .
C13 N1 H1D 127.9 . .
C15 N2 C14 108.26(19) . .
C15 N2 H2A 122.2 . .
C14 N2 H2A 129.5 . .
C8 O1 H3A 110.2 . .
C9 O3 H3A 108.8 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.499(3) .
C1 H1A 0.9600 .
C1 H1B 0.9600 .
C1 H1C 0.9600 .
C2 C3 1.377(3) .
C2 C7 1.387(3) .
C3 C4 1.379(3) .
C3 H3 0.9300 .
C4 C5 1.393(3) .
C4 H4 0.9300 .
C5 C6 1.412(3) .
C5 C9 1.513(3) .
C6 C7 1.393(3) .
C6 C8 1.510(3) .
C7 H7 0.9300 .
C8 O2 1.230(3) .
C8 O1 1.272(3) .
C9 O4 1.225(3) .
C9 O3 1.281(3) .
C10 C12 1.379(3) 3_655
C10 C11 1.384(3) .
C10 H10 0.9300 .
C11 C12 1.388(3) .
C11 C13 1.466(3) .
C12 H12 0.9300 .
C13 C14 1.354(3) .
C13 N1 1.379(3) .
C14 N2 1.375(3) .
C14 H14 0.9300 .
C15 N2 1.309(3) .
C15 N1 1.322(3) .
C15 H15 0.9300 .
N1 H1D 0.9119 .
N2 H2A 1.0030 .
O1 H3A 1.2275 .
O3 H3A 1.1504 .
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
C7 C2 C3 C4 0.0(3) . . . .
C1 C2 C3 C4 179.5(2) . . . .
C2 C3 C4 C5 1.4(4) . . . .
C3 C4 C5 C6 -1.4(3) . . . .
C3 C4 C5 C9 -179.7(2) . . . .
C4 C5 C6 C7 0.1(3) . . . .
C9 C5 C6 C7 178.1(2) . . . .
C4 C5 C6 C8 -178.8(2) . . . .
C9 C5 C6 C8 -0.8(4) . . . .
C3 C2 C7 C6 -1.3(3) . . . .
C1 C2 C7 C6 179.1(2) . . . .
C5 C6 C7 C2 1.3(3) . . . .
C8 C6 C7 C2 -179.6(2) . . . .
C7 C6 C8 O2 -7.3(3) . . . .
C5 C6 C8 O2 171.7(2) . . . .
C7 C6 C8 O1 172.5(2) . . . .
C5 C6 C8 O1 -8.5(4) . . . .
C4 C5 C9 O4 4.9(3) . . . .
C6 C5 C9 O4 -173.2(2) . . . .
C4 C5 C9 O3 -175.1(2) . . . .
C6 C5 C9 O3 6.8(4) . . . .
C12 C10 C11 C12 0.0(4) 3_655 . . .
C12 C10 C11 C13 179.3(2) 3_655 . . .
C10 C11 C12 C10 0.0(4) . . . 3_655
C13 C11 C12 C10 -179.3(2) . . . 3_655
C10 C11 C13 C14 6.3(3) . . . .
C12 C11 C13 C14 -174.5(2) . . . .
C10 C11 C13 N1 -173.15(19) . . . .
C12 C11 C13 N1 6.1(3) . . . .
N1 C13 C14 N2 -0.1(2) . . . .
C11 C13 C14 N2 -179.6(2) . . . .
N2 C15 N1 C13 0.4(2) . . . .
C14 C13 N1 C15 -0.2(2) . . . .
C11 C13 N1 C15 179.38(19) . . . .
N1 C15 N2 C14 -0.4(2) . . . .
C13 C14 N2 C15 0.3(3) . . . .
