Synthesis and crystal structure of 6-carboxy-1-(3,5-dicarboxyphenyl)-1H-benzo[d]imidazol-3-ium-5-carboxylate dihydrate, C18H12N2O8
Yun, Meng; Dong, Xiu-Yan; Zeitschrift für Kristallographie - New Crystal Structures 233 (2018) 633–634; doi:10.1515/ncrs-2017-0396

data_8106240
_publ_section_title
;
 Synthesis and crystal structure of
 6-carboxy-1-(3,5-dicarboxyphenyl)-1H-benzo[d]imidazol-3-ium-5-carboxylate
 dihydrate, C18H12N2O8
;
_journal_issue                   4
_journal_name_full
'Zeitschrift f\"ur Kristallographie - New Crystal Structures'
_journal_page_first              633
_journal_page_last               634
_journal_paper_doi               10.1515/ncrs-2017-0396
_journal_volume                  233
_journal_year                    2018
_chemical_formula_moiety         'C18 H12 N2 O8, 2(H2 O)'
_chemical_formula_sum            'C18 H16 N2 O10'
_chemical_formula_weight         420.33
_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   mixed
_atom_sites_solution_primary     direct
_cell_angle_alpha                66.892(3)
_cell_angle_beta                 86.069(3)
_cell_angle_gamma                81.658(4)
_cell_formula_units_Z            2
_cell_length_a                   8.4592(10)
_cell_length_b                   9.8442(11)
_cell_length_c                   11.2565(12)
_cell_measurement_reflns_used    2475
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.43
_cell_measurement_theta_min      2.27
_cell_volume                     852.97(17)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS-1997 (Sheldrick, 2008)'
_diffrn_ambient_temperature      153.15
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_av_unetI/netI     0.0647
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7338
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_min         2.268
_exptl_absorpt_coefficient_mu    0.136
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.637
_exptl_crystal_description
;
;
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.367
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     287
_refine_ls_number_reflns         3876
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0938
_refine_ls_R_factor_gt           0.0609
_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/[\s^2^(Fo^2^)+(0.0607P)^2^+0.8921P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1395
_refine_ls_wR_factor_ref         0.1557
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2732
_reflns_number_total             3876
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            suppl_ncrs-2017-0396_suppl.cif
_cod_data_source_block           zd_d2_0m_a_sq
_cod_database_code               8106240
_shelx_estimated_absorpt_t_max   0.976
_shelx_estimated_absorpt_t_min   0.971
_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, All O(H,H) groups
2. Restrained distances
 H9B-O9
 0.84 with sigma of 0.02
 O8-H8
 0.84 with sigma of 0.02
 O9-H9A
 0.84 with sigma of 0.02
 O10-H10D
 0.84 with sigma of 0.02
 O10-H10C
 0.84 with sigma of 0.02
3.a Free rotating group:
 O9(H9A), O10(H10C,H10D)
3.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
3.c Aromatic/amide H refined with riding coordinates:
 N1(H1A), C14(H14), C16(H16), C12(H12), C9(H9), C3(H3), C6(H6A)
3.d Idealised tetrahedral OH refined as rotating group:
 O6(H6), O1(H1)
;
_shelx_res_checksum              19882
_shelx_hkl_checksum              43796
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'