#------------------------------------------------------------------------------
#$Date: 2023-05-23 11:30:15 +0300 (Tue, 23 May 2023) $
#$Revision: 283958 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/72/8107252.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_8107252
loop_
_publ_author_name
'Lu, Zhi-Qiang'
_publ_section_title
;
 Crystal structure of 5,5′-(1,4-phenylene)bis(1H-imidazol-3-ium)
 bis(2-(2-(carboxymethyl)phenyl)acetate), C32H30N4O8
;
_journal_issue                   5
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              921
_journal_page_last               922
_journal_paper_doi               10.1515/ncrs-2022-0281
_journal_volume                  237
_journal_year                    2022
_chemical_formula_moiety         '2(C10 H9 O4), C12 H12 N4'
_chemical_formula_sum            'C32 H30 N4 O8'
_chemical_formula_weight         598.60
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 96.8070(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.4698(10)
_cell_length_b                   10.9797(12)
_cell_length_c                   14.0366(15)
_cell_measurement_reflns_used    3312
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.846
_cell_measurement_theta_min      2.361
_cell_volume                     1449.2(3)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Smart Apex CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  graphite
_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  0.0234
_diffrn_reflns_av_unetI/netI     0.0219
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9861
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.852
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; Bruker,2000'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             628
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2545
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0392
_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)+(0.0602P)²+0.3695P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1032
_refine_ls_wR_factor_ref         0.1087
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2029
_reflns_number_total             2545
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2022-0281_suppl.cif
_cod_data_source_block           a
_cod_database_code               8107252
_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.
;
_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 O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4A), N1(H1A), N2(H2A), C11(H11), C13(H13),
 C15(H15), C16(H16)
2.c Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'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_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
O1 O 0.21822(13) 0.16393(12) 0.23258(9) 0.0447(3) Uani 1 1 d . . . . .
O2 O 0.12210(15) 0.29655(14) 0.32479(9) 0.0606(4) Uani 1 1 d . . . . .
O3 O 0.22075(13) -0.13768(12) 0.22593(9) 0.0466(3) Uani 1 1 d . . . . .
O4 O 0.03828(14) -0.09800(14) 0.30725(10) 0.0548(4) Uani 1 1 d . . . . .
H4 H -0.006344 -0.136267 0.263390 0.082 Uiso 1 1 calc R U . . .
C1 C 0.58165(19) 0.14413(19) 0.36385(13) 0.0450(5) Uani 1 1 d . . . . .
H1 H 0.602236 0.226936 0.363479 0.054 Uiso 1 1 calc R U . . .
C2 C 0.6874(2) 0.0623(2) 0.35421(14) 0.0572(6) Uani 1 1 d . . . . .
H2 H 0.779113 0.089262 0.348477 0.069 Uiso 1 1 calc R U . . .
C3 C 0.6580(2) -0.0590(2) 0.35305(15) 0.0629(7) Uani 1 1 d . . . . .
H3 H 0.729645 -0.115198 0.346151 0.075 Uiso 1 1 calc R U . . .
C4 C 0.5220(3) -0.09884(18) 0.36209(14) 0.0549(6) Uani 1 1 d . . . . .
H4A H 0.502986 -0.181966 0.360818 0.066 Uiso 1 1 calc R U . . .
C5 C 0.41235(19) -0.01707(15) 0.37310(11) 0.0351(4) Uani 1 1 d . . . . .
C6 C 0.44397(17) 0.10708(15) 0.37420(11) 0.0324(4) Uani 1 1 d . . . . .
C7 C 0.3353(2) 0.20366(18) 0.38930(13) 0.0456(5) Uani 1 1 d . . . . .
H7A H 0.384636 0.280689 0.400527 0.055 Uiso 1 1 calc R U . . .
H7B H 0.293377 0.183695 0.447123 0.055 Uiso 1 1 calc R U . . .
C8 C 0.21595(17) 0.22130(15) 0.30849(12) 0.0346(4) Uani 1 1 d . . . . .
C9 C 0.2661(2) -0.06243(19) 0.38690(13) 0.0508(5) Uani 1 1 d . . . . .
H9A H 0.276452 -0.130955 0.430785 0.061 Uiso 1 1 calc R U . . .
H9B H 0.217070 0.001578 0.417459 0.061 Uiso 1 1 calc R U . . .
C10 C 0.17375(19) -0.10143(16) 0.29772(13) 0.0383(4) Uani 1 1 d . . . . .
N1 N 1.00003(15) 0.14205(13) 0.10357(10) 0.0385(4) Uani 1 1 d . . . . .
H1A H 1.071742 0.156174 0.145692 0.046 Uiso 1 1 calc R U . . .
N2 N 0.86829(14) 0.12664(13) -0.03169(10) 0.0347(3) Uani 1 1 d . . . . .
H2A H 0.841344 0.129337 -0.092354 0.042 Uiso 1 1 calc R U . . .
C11 C 0.54931(18) 0.04824(15) 0.08849(12) 0.0346(4) Uani 1 1 d . . . . .
H11 H 0.582445 0.080688 0.148172 0.042 Uiso 1 1 calc R U . . .
C12 C 0.63930(17) 0.04427(14) 0.01652(11) 0.0298(4) Uani 1 1 d . . . . .
C13 C 0.58789(18) -0.00471(15) -0.07214(12) 0.0347(4) Uani 1 1 d . . . . .
H13 H 0.646489 -0.008121 -0.120768 0.042 Uiso 1 1 calc R U . . .
C14 C 0.78590(17) 0.08888(14) 0.03739(11) 0.0305(4) Uani 1 1 d . . . . .
C15 C 0.87034(18) 0.09888(16) 0.12181(12) 0.0364(4) Uani 1 1 d . . . . .
H15 H 0.844638 0.079688 0.181944 0.044 Uiso 1 1 calc R U . . .
C16 C 0.99595(18) 0.15817(16) 0.01053(12) 0.0384(4) Uani 1 1 d . . . . .
H16 H 1.070512 0.187022 -0.020736 0.046 Uiso 1 1 calc R U . . .
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
C10 O4 H4 109.5 . .
C2 C1 H1 119.1 . .
C2 C1 C6 121.8(2) . .
C6 C1 H1 119.1 . .
C1 C2 H2 120.2 . .
C3 C2 C1 119.6(2) . .
C3 C2 H2 120.2 . .
C2 C3 H3 120.0 . .
C2 C3 C4 120.03(19) . .
C4 C3 H3 120.0 . .
C3 C4 H4A 119.3 . .
C3 C4 C5 121.4(2) . .
C5 C4 H4A 119.3 . .
C4 C5 C6 117.94(17) . .
C4 C5 C9 120.62(18) . .
C6 C5 C9 121.41(17) . .
C1 C6 C5 119.18(16) . .
C1 C6 C7 118.19(17) . .
C5 C6 C7 122.60(16) . .
C6 C7 H7A 108.2 . .
C6 C7 H7B 108.2 . .
C6 C7 C8 116.41(14) . .
H7A C7 H7B 107.3 . .
C8 C7 H7A 108.2 . .
C8 C7 H7B 108.2 . .
O1 C8 O2 125.19(16) . .
O1 C8 C7 119.39(15) . .
O2 C8 C7 115.42(15) . .
C5 C9 H9A 108.2 . .
C5 C9 H9B 108.2 . .
H9A C9 H9B 107.4 . .
C10 C9 C5 116.15(15) . .
C10 C9 H9A 108.2 . .
C10 C9 H9B 108.2 . .
O3 C10 O4 123.70(16) . .
O3 C10 C9 123.36(17) . .
O4 C10 C9 112.86(16) . .
C15 N1 H1A 125.9 . .
C16 N1 H1A 125.9 . .
C16 N1 C15 108.13(14) . .
C14 N2 H2A 125.5 . .
C16 N2 H2A 125.5 . .
C16 N2 C14 109.02(14) . .
C12 C11 H11 119.6 . .
C13 C11 H11 119.6 3_655 .
C13 C11 C12 120.84(16) 3_655 .
C11 C12 C14 119.24(14) . .
C13 C12 C11 118.72(15) . .
C13 C12 C14 122.02(15) . .
C11 C13 C12 120.44(16) 3_655 .
C11 C13 H13 119.8 3_655 .
C12 C13 H13 119.8 . .
N2 C14 C12 124.09(14) . .
C15 C14 N2 105.46(14) . .
C15 C14 C12 130.42(15) . .
N1 C15 H15 125.8 . .
C14 C15 N1 108.34(15) . .
C14 C15 H15 125.8 . .
N1 C16 N2 109.05(15) . .
N1 C16 H16 125.5 . .
N2 C16 H16 125.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C8 1.240(2) .
O2 C8 1.254(2) .
O3 C10 1.216(2) .
O4 H4 0.8200 .
O4 C10 1.306(2) .
C1 H1 0.9300 .
C1 C2 1.364(3) .
C1 C6 1.390(2) .
C2 H2 0.9300 .
C2 C3 1.360(3) .
C3 H3 0.9300 .
C3 C4 1.381(3) .
C4 H4A 0.9300 .
C4 C5 1.395(3) .
C5 C6 1.395(2) .
C5 C9 1.506(3) .
C6 C7 1.510(2) .
C7 H7A 0.9700 .
C7 H7B 0.9700 .
C7 C8 1.516(2) .
C9 H9A 0.9700 .
C9 H9B 0.9700 .
C9 C10 1.502(2) .
N1 H1A 0.8600 .
N1 C15 1.369(2) .
N1 C16 1.314(2) .
N2 H2A 0.8600 .
N2 C14 1.379(2) .
N2 C16 1.328(2) .
C11 H11 0.9300 .
C11 C12 1.397(2) .
C11 C13 1.378(2) 3_655
C12 C13 1.390(2) .
C12 C14 1.469(2) .
C13 H13 0.9300 .
C14 C15 1.353(2) .
C15 H15 0.9300 .
C16 H16 0.9300 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O4 H4 O2 0.82 1.72 2.5328(18) 171.2 2_545 yes
N1 H1A O1 0.86 1.74 2.5921(18) 172.4 1_655 yes
N2 H2A O3 0.86 1.90 2.7595(19) 178.9 3_655 yes
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 -0.3(3) . . . .
C1 C6 C7 C8 112.32(19) . . . .
C2 C1 C6 C5 -1.1(3) . . . .
C2 C1 C6 C7 177.05(17) . . . .
C2 C3 C4 C5 -0.4(3) . . . .
C3 C4 C5 C6 0.3(3) . . . .
C3 C4 C5 C9 -177.48(17) . . . .
C4 C5 C6 C1 0.4(2) . . . .
C4 C5 C6 C7 -177.70(16) . . . .
C4 C5 C9 C10 -80.1(2) . . . .
C5 C6 C7 C8 -69.6(2) . . . .
C5 C9 C10 O3 26.1(3) . . . .
C5 C9 C10 O4 -157.11(17) . . . .
C6 C1 C2 C3 1.1(3) . . . .
C6 C5 C9 C10 102.1(2) . . . .
C6 C7 C8 O1 -5.3(3) . . . .
C6 C7 C8 O2 175.78(17) . . . .
C9 C5 C6 C1 178.18(15) . . . .
C9 C5 C6 C7 0.1(2) . . . .
N2 C14 C15 N1 0.22(19) . . . .
C11 C12 C13 C11 0.1(3) . . . 3_655
C11 C12 C14 N2 -157.97(15) . . . .
C11 C12 C14 C15 24.5(3) . . . .
C12 C14 C15 N1 178.09(16) . . . .
C13 C11 C12 C13 -0.1(3) 3_655 . . .
C13 C11 C12 C14 -178.56(15) 3_655 . . .
C13 C12 C14 N2 23.6(2) . . . .
C13 C12 C14 C15 -153.91(18) . . . .
C14 N2 C16 N1 0.3(2) . . . .
C14 C12 C13 C11 178.51(15) . . . 3_655
C15 N1 C16 N2 -0.1(2) . . . .
C16 N1 C15 C14 -0.1(2) . . . .
C16 N2 C14 C12 -178.34(15) . . . .
C16 N2 C14 C15 -0.29(18) . . . .
