Quantitative analysis of intermolecular interactions in cocrystals and a pair of polymorphous cocrystal hydrates from 1,4-dihydroquinoxaline-2,3-dione and 1H-benzo[d]imidazol-2(3H)-one with 2,5-dihydroxy-1,4-benzoquinones: A combined X-ray structure and theoretical analysis
Sosa-Rivadeneyra, Martha Virginia; Perumal, Venkatesan; Flores-Manuel, Fermin; Bernès, Sylvain; Höpfl, Herbert; Ceron, Margarita; Thamotharan, Subbiah; Percino, M. Judith; CrystEngComm  (2020) –; doi:10.1039/D0CE01056A

data_7241095
_publ_section_title
;
 Quantitative analysis of intermolecular interactions in cocrystals and a
 pair of polymorphous cocrystal hydrates from
 1,4-dihydroquinoxaline-2,3-dione and 1H-benzo[d]imidazol-2(3H)-one with
 2,5-dihydroxy-1,4-benzoquinones: A combined X-ray structure and
 theoretical analysis
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D0CE01056A
_journal_year                    2020
_chemical_formula_moiety         'C6 H2 Cl2 O4, 2(C8 H6 N2 O2), 2(H2 O)'
_chemical_formula_sum            'C22 H18 Cl2 N4 O10'
_chemical_formula_weight         569.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-03-21
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-07-14 deposited with the CCDC.	2020-08-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 132.364(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   27.986(3)
_cell_length_b                   4.6150(3)
_cell_length_c                   24.046(2)
_cell_measurement_reflns_used    7909
_cell_measurement_temperature    295(1)
_cell_measurement_theta_max      23.60
_cell_measurement_theta_min      2.76
_cell_volume                     2294.7(4)
_computing_cell_refinement       'X-AREA 1.86'
_computing_data_collection       'X-AREA 1.86 (Stoe & Cie, 2018)'
_computing_data_reduction        'X-AREA 1.86'
_computing_molecular_graphics
'XP in SHELXTL-Plus (Sheldrick, 2008) and Mercury (Macrae et al., 2008)'
_computing_publication_material  'PublCif (Westrip, 2010)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015a)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295(1)
_diffrn_detector                 'Reverse-biased silicon diode array'
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_type            'Dectris Pilatus 100K R'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
1261 frames, 50-55 s/frame, 1 deg./frame, detector distance = 50 mm
;
_diffrn_measurement_device       'Eulerian four-circle diffractometer'
_diffrn_measurement_device_type  'Stoe Stadivari'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support Mitegen
_diffrn_radiation_collimation    '0.6 mm diameter'
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_polarisn_norm  -90
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           AgK\a
_diffrn_radiation_wavelength     0.56083
_diffrn_reflns_av_R_equivalents  0.1091
_diffrn_reflns_av_unetI/netI     0.0799
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            25780
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        19.664
_diffrn_reflns_theta_max         20.993
_diffrn_reflns_theta_min         2.757
_diffrn_source                   'Sealed X-ray tube'
_diffrn_source_current           0.55
_diffrn_source_power             0.03575
_diffrn_source_type              'Axo Astix-f Microfocus source'
_diffrn_source_voltage           65
_exptl_absorpt_coefficient_mu    0.189
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.3249
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'X-AREA 1.86 (Stoe & Cie, 2018)'
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    1.648
_exptl_crystal_description       Needle
_exptl_crystal_F_000             1168
_exptl_crystal_recrystallization_method
;
Re-cristallisation from solvent: Ethanol
;
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.741
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     187
_refine_ls_number_reflns         2487
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.741
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0329
_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^)+(0.0218P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0579
_refine_ls_wR_factor_ref         0.0627
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1413
_reflns_number_total             2487
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ce01056a2.cif
_cod_data_source_block           IB_2H2O
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7241095
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.895
_shelx_estimated_absorpt_t_max   0.991
_shelx_res_checksum              7680