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#$Date: 2022-10-21 09:56:21 +0300 (Fri, 21 Oct 2022) $
#$Revision: 278683 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/59/8105916.cif $
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#
# 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.
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data_8105916
loop_
_publ_author_name
'Li, Xiao-Fei'
'Wang, Ke'
'Zhang, Wei'
'Fu, Zi-Ying'
_publ_section_title
;
 Crystal structure of
 5-carboxy-2-(2-carboxyphenyl)-1H-imidazol-3-ium-4-carboxylate dihydrate,
 C12H8N2O6⋅2(H2O)
;
_journal_issue                   5
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              993
_journal_page_last               995
_journal_paper_doi               10.1515/ncrs-2019-0209
_journal_volume                  234
_journal_year                    2019
_chemical_formula_moiety         'C12 H8 N2 O6, 2(H2 O)'
_chemical_formula_sum            'C12 H12 N2 O8'
_chemical_formula_weight         312.24
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 95.152(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.1122(5)
_cell_length_b                   15.0150(13)
_cell_length_c                   17.3561(15)
_cell_measurement_reflns_used    5543
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      2.96
_cell_volume                     1326.9(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker D8 VENTURE'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1096
_diffrn_reflns_av_unetI/netI     0.0587
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            18986
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.496
_diffrn_reflns_theta_min         3.595
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.134
_exptl_absorpt_correction_T_max  0.9802
_exptl_absorpt_correction_T_min  0.9737
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS(Bruker 2000)'
_exptl_crystal_colour            pale-yelow
_exptl_crystal_density_diffrn    1.563
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.150
_exptl_transmission_factor_max   0.7456
_exptl_transmission_factor_min   0.6625
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       0.038(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2435
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.1126
_refine_ls_R_factor_gt           0.0711
_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)+(0.0455P)²+1.8139P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1325
_refine_ls_wR_factor_ref         0.1509
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1640
_reflns_number_total             2435
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2019-0209_suppl.cif
_cod_data_source_block           exp_I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               8105916
_shelx_shelxl_version_number     2014/7
_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   0.980
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 0.1247(8) 0.8599(3) 0.5260(2) 0.0420(9) Uani 1 1 d . . . . .
C2 C 0.1692(7) 0.8308(2) 0.60812(18) 0.0311(8) Uani 1 1 d . . . . .
C3 C 0.0568(6) 0.7662(2) 0.64908(18) 0.0311(8) Uani 1 1 d . . . . .
C4 C -0.1660(7) 0.7044(2) 0.6285(2) 0.0390(9) Uani 1 1 d . . . . .
C5 C 0.3458(6) 0.8370(2) 0.72830(17) 0.0277(7) Uani 1 1 d . . . . .
C6 C 0.4979(6) 0.8640(2) 0.80093(17) 0.0262(7) Uani 1 1 d . . . . .
C7 C 0.6888(7) 0.8062(2) 0.83288(19) 0.0345(8) Uani 1 1 d . . . . .
H7 H 0.7193 0.7526 0.8083 0.041 Uiso 1 1 calc R U . . .
C8 C 0.8337(7) 0.8280(2) 0.9011(2) 0.0392(9) Uani 1 1 d . . . . .
H8 H 0.9625 0.7892 0.9223 0.047 Uiso 1 1 calc R U . . .
C9 C 0.7888(7) 0.9068(2) 0.9380(2) 0.0402(9) Uani 1 1 d . . . . .
H9A H 0.8888 0.9215 0.9836 0.048 Uiso 1 1 calc R U . . .
C10 C 0.5952(7) 0.9644(2) 0.90726(19) 0.0367(9) Uani 1 1 d . . . . .
H10 H 0.5670 1.0178 0.9323 0.044 Uiso 1 1 calc R U . . .
C11 C 0.4424(6) 0.9432(2) 0.83936(18) 0.0285(8) Uani 1 1 d . . . . .
C12 C 0.2128(7) 0.9992(2) 0.81161(19) 0.0317(8) Uani 1 1 d . . . . .
N1 N 0.1733(5) 0.77065(18) 0.72317(14) 0.0298(7) Uani 1 1 d . . . . .
H1 H 0.1587 0.7305 0.7578 0.036 Uiso 1 1 d R U . . .
N2 N 0.3512(5) 0.87328(19) 0.65835(14) 0.0308(7) Uani 1 1 d . . . . .
H2 H 0.4576 0.9157 0.6497 0.037 Uiso 1 1 d R U . . .
O1 O 0.2573(6) 0.9210(2) 0.50391(15) 0.0630(9) Uani 1 1 d . . . . .
O2 O -0.0518(6) 0.8172(2) 0.48355(14) 0.0552(8) Uani 1 1 d . . . . .
H2A H -0.1182 0.7780 0.5083 0.083 Uiso 1 1 d R U . . .
O3 O -0.2574(6) 0.7022(2) 0.55792(15) 0.0579(9) Uani 1 1 d . . . . .
O4 O -0.2516(5) 0.66094(17) 0.68109(15) 0.0464(7) Uani 1 1 d . . . . .
O5 O 0.0592(5) 0.97870(17) 0.75754(14) 0.0451(7) Uani 1 1 d . . . . .
O6 O 0.1864(5) 1.07076(17) 0.85429(15) 0.0451(7) Uani 1 1 d . . . . .
H6 H 0.0452 1.0939 0.8398 0.068 Uiso 1 1 d R U . . .
O7 O 0.1914(6) 0.65082(18) 0.83658(14) 0.0550(8) Uani 1 1 d . . . . .
H7A H 0.0720 0.6119 0.8399 0.082 Uiso 1 1 d R U . . .
H7B H 0.2960 0.6585 0.8769 0.082 Uiso 1 1 d R U . . .
O8 O 0.6702(5) 1.01571(17) 0.64087(14) 0.0442(7) Uani 1 1 d . . . . .
H8A H 0.8029 1.0137 0.6741 0.066 Uiso 1 1 d R U . . .
H8B H 0.7041 1.0358 0.5971 0.066 Uiso 1 1 d 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
O1 C1 O2 125.2(3) . .
O1 C1 C2 118.6(3) . .
O2 C1 C2 116.2(3) . .
C3 C2 N2 107.1(3) . .
C3 C2 C1 132.4(3) . .
N2 C2 C1 120.5(3) . .
C2 C3 N1 106.7(3) . .
C2 C3 C4 132.1(3) . .
N1 C3 C4 121.0(3) . .
O4 C4 O3 125.1(3) . .
O4 C4 C3 117.9(3) . .
O3 C4 C3 117.0(3) . .
N1 C5 N2 108.3(3) . .
N1 C5 C6 124.0(3) . .
N2 C5 C6 127.7(3) . .
C7 C6 C11 120.4(3) . .
C7 C6 C5 117.9(3) . .
C11 C6 C5 121.6(3) . .
C8 C7 C6 120.0(3) . .
C8 C7 H7 120.0 . .
C6 C7 H7 120.0 . .
C9 C8 C7 120.4(3) . .
C9 C8 H8 119.8 . .
C7 C8 H8 119.8 . .
C8 C9 C10 120.1(3) . .
C8 C9 H9A 119.9 . .
C10 C9 H9A 119.9 . .
C9 C10 C11 120.7(3) . .
C9 C10 H10 119.6 . .
C11 C10 H10 119.6 . .
C10 C11 C6 118.3(3) . .
C10 C11 C12 120.8(3) . .
C6 C11 C12 120.8(3) . .
O5 C12 O6 123.5(3) . .
O5 C12 C11 123.1(3) . .
O6 C12 C11 113.3(3) . .
C5 N1 C3 109.3(3) . .
C5 N1 H1 125.3 . .
C3 N1 H1 124.4 . .
C5 N2 C2 108.6(3) . .
C5 N2 H2 121.9 . .
C2 N2 H2 129.5 . .
C1 O2 H2A 111.1 . .
C12 O6 H6 107.7 . .
H7A O7 H7B 116.2 . .
H8A O8 H8B 113.8 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1 1.223(5) .
C1 O2 1.284(4) .
C1 C2 1.489(5) .
C2 C3 1.360(5) .
C2 N2 1.374(4) .
C3 N1 1.369(4) .
C3 C4 1.488(5) .
C4 O4 1.233(4) .
C4 O3 1.272(4) .
C5 N1 1.328(4) .
C5 N2 1.333(4) .
C5 C6 1.477(4) .
C6 C7 1.384(5) .
C6 C11 1.405(4) .
C7 C8 1.379(5) .
C7 H7 0.9300 .
C8 C9 1.373(5) .
C8 H8 0.9300 .
C9 C10 1.384(5) .
C9 H9A 0.9300 .
C10 C11 1.391(5) .
C10 H10 0.9300 .
C11 C12 1.488(5) .
C12 O5 1.208(4) .
C12 O6 1.319(4) .
N1 H1 0.8599 .
N2 H2 0.8600 .
O2 H2A 0.8200 .
O6 H6 0.8200 .
O7 H7A 0.8500 .
O7 H7B 0.8500 .
O8 H8A 0.8502 .
O8 H8B 0.8499 .
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
N1 H1 O7 0.86 1.81 2.662(4) 169.2 .
N2 H2 O8 0.86 1.87 2.723(4) 172.7 .
O2 H2A O3 0.82 1.63 2.448(4) 178.3 .
O6 H6 O4 0.82 1.82 2.628(3) 170.0 2_456
O7 H7A O8 0.85 1.95 2.796(4) 172.0 2_546
O7 H7B O2 0.85 1.98 2.804(3) 164.3 4_676
O8 H8A O5 0.85 1.94 2.764(3) 164.1 1_655
O8 H8B O1 0.85 1.90 2.742(4) 174.1 3_676
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
O1 C1 C2 C3 -179.8(4) . . . .
O2 C1 C2 C3 -0.2(6) . . . .
O1 C1 C2 N2 1.4(5) . . . .
O2 C1 C2 N2 -179.0(3) . . . .
N2 C2 C3 N1 -0.2(4) . . . .
C1 C2 C3 N1 -179.1(4) . . . .
N2 C2 C3 C4 174.0(4) . . . .
C1 C2 C3 C4 -5.0(7) . . . .
C2 C3 C4 O4 -169.5(4) . . . .
N1 C3 C4 O4 3.9(5) . . . .
C2 C3 C4 O3 8.9(6) . . . .
N1 C3 C4 O3 -177.7(3) . . . .
N1 C5 C6 C7 68.8(4) . . . .
N2 C5 C6 C7 -112.1(4) . . . .
N1 C5 C6 C11 -107.5(4) . . . .
N2 C5 C6 C11 71.5(5) . . . .
C11 C6 C7 C8 -2.9(5) . . . .
C5 C6 C7 C8 -179.2(3) . . . .
C6 C7 C8 C9 0.4(6) . . . .
C7 C8 C9 C10 0.8(6) . . . .
C8 C9 C10 C11 0.5(6) . . . .
C9 C10 C11 C6 -2.9(5) . . . .
C9 C10 C11 C12 172.2(3) . . . .
C7 C6 C11 C10 4.1(5) . . . .
C5 C6 C11 C10 -179.7(3) . . . .
C7 C6 C11 C12 -171.1(3) . . . .
C5 C6 C11 C12 5.2(5) . . . .
C10 C11 C12 O5 -172.3(3) . . . .
C6 C11 C12 O5 2.7(5) . . . .
C10 C11 C12 O6 4.4(5) . . . .
C6 C11 C12 O6 179.5(3) . . . .
N2 C5 N1 C3 -2.5(4) . . . .
C6 C5 N1 C3 176.7(3) . . . .
C2 C3 N1 C5 1.6(4) . . . .
C4 C3 N1 C5 -173.3(3) . . . .
N1 C5 N2 C2 2.4(4) . . . .
C6 C5 N2 C2 -176.8(3) . . . .
C3 C2 N2 C5 -1.4(4) . . . .
C1 C2 N2 C5 177.7(3) . . . .
