The crystal structure of 4-hydroxy-2,5-bis(1-methyl-1H-imidazol-3-ium-2-ylthio)-3,6-dioxocyclohexa-1,4-dienolate chloride monohydrate, C14H15N4O5S2Cl
Miao, Ming-zhi; Li, Ji; Zeitschrift für Kristallographie - New Crystal Structures 236 (2021) 189–191; doi:10.1515/ncrs-2020-0501

data_8104919
_publ_section_title
;
 The crystal structure of
 4-hydroxy-2,5-bis(1-methyl-1H-imidazol-3-ium-2-ylthio)-3,6-dioxocyclohexa-1,4-dienolate
 chloride monohydrate, C14H15N4O5S2Cl
;
_journal_issue                   1
_journal_name_full
'Zeitschrift f\"ur Kristallographie - New Crystal Structures'
_journal_page_first              189
_journal_page_last               191
_journal_paper_doi               10.1515/ncrs-2020-0501
_journal_volume                  236
_journal_year                    2021
_chemical_formula_moiety         'C14 H13 N4 O4 S2, Cl, H2 O'
_chemical_formula_sum            'C14 H15 Cl N4 O5 S2'
_chemical_formula_weight         418.87
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.1956(11)
_cell_length_b                   11.7856(8)
_cell_length_c                   18.7814(13)
_cell_measurement_reflns_used    9798
_cell_measurement_temperature    292(1)
_cell_measurement_theta_max      27.54
_cell_measurement_theta_min      2.40
_cell_volume                     3584.9(4)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2003) [1]'
_computing_data_collection       'Bruker Apex II'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2003)'
_computing_molecular_graphics    'Diamond (Brandenburg, 2006)[4]'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)[6]'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015) [2-3]'
_computing_structure_solution    'ShelXS (Sheldrick, 2015) [2-3]'
_diffrn_ambient_temperature      292(1)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker Apex II CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0640
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            29558
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.000
_diffrn_reflns_theta_min         2.169
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.481
_exptl_absorpt_correction_T_max  0.9100
_exptl_absorpt_correction_T_min  0.8693
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, (Sheldrick, 2008)[5]'
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1728
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.389
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     252
_refine_ls_number_reflns         4287
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0459
_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/[\s^2^(Fo^2^)+(0.0692P)^2^+0.9380P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1166
_refine_ls_wR_factor_ref         0.1218
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3527
_reflns_number_total             4287
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            suppl_j_ncrs-2020-0501_suppl.cif
_cod_data_source_block           t
_cod_database_code               8104919
_shelx_estimated_absorpt_t_max   0.954
_shelx_estimated_absorpt_t_min   0.869
_exptl_absorpt_special_details   'SADABS, (Sheldrick, 2008)[5]'
_olex2_refinement_description
; 
1. Fixed Uiso 
 At 1.2 times of: 
  All C(H) groups, All N(H) groups, All O(H) groups 
 At 1.5 times of: 
  All C(H,H,H) groups, All O(H,H) groups 
2. Restrained distances 
 N2-H2A = N4-H4 
 0.86 with sigma of 0.01 
 H5B-H5A 
 1.39 with sigma of 0.02 
 O5-H5B = O5-H5A = O3-H3A 
 0.82 with sigma of 0.01 
3.a Aromatic/amide H refined with riding coordinates: 
 C2(H2), C3(H3), C12(H12), C13(H13) 
3.b Idealised Me refined as rotating group: 
 C1(H1A,H1B,H1C), C14(H14A,H14B,H14C) 
;