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#$Date: 2020-08-22 04:53:03 +0300 (Sat, 22 Aug 2020) $
#$Revision: 255571 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/10/7241094.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_7241094
loop_
_publ_author_name
'Sosa-Rivadeneyra, Martha Virginia'
'Perumal, Venkatesan'
'Flores-Manuel, Fermin'
'Bernès, Sylvain'
'Höpfl, Herbert'
'Ceron, Margarita'
'Thamotharan, Subbiah'
'Percino, M. Judith'
_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 H4 O4, 2(C7 H6 N2 O)'
_chemical_formula_sum            'C20 H16 N4 O6'
_chemical_formula_weight         408.37
_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     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-11-29
_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                 90.109(9)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.2947(6)
_cell_length_b                   8.1240(7)
_cell_length_c                   20.880(3)
_cell_measurement_reflns_used    11441
_cell_measurement_temperature    295(1)
_cell_measurement_theta_max      25.55
_cell_measurement_theta_min      2.51
_cell_volume                     898.13(18)
_computing_cell_refinement       'X-AREA 1.82'
_computing_data_collection       'X-AREA 1.82 (Stoe & Cie, 2018)'
_computing_data_reduction        'X-AREA 1.82'
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
1140 frames, 120 s/frame, 1 deg./frame, detector distance = 40 mm
;
_diffrn_measurement_device       'Eulerian four-circle diffractometer'
_diffrn_measurement_device_type  'Stoe Stadivari'
_diffrn_measurement_method       'ω 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  0.0698
_diffrn_reflns_av_unetI/netI     0.0352
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            19443
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        19.664
_diffrn_reflns_theta_max         21.000
_diffrn_reflns_theta_min         2.507
_diffrn_source                   'Sealed X-ray tube'
_diffrn_source_current           0.600
_diffrn_source_power             0.039
_diffrn_source_type              'Axo Astix-f Microfocus source'
_diffrn_source_voltage           65
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.3515
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'X-AREA 1.82 (Stoe & Cie, 2018)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.510
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_recrystallization_method
;
Re-cristallisation from solvent: Acetonitrile
;
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.151
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.906
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     146
_refine_ls_number_reflns         1966
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.906
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0398
_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)+(0.0637P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0938
_refine_ls_wR_factor_ref         0.1021
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1410
_reflns_number_total             1966
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ce01056a2.cif
_cod_data_source_block           III
_cod_original_cell_volume        898.13(17)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7241094
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.986
_shelx_estimated_absorpt_t_max   0.993
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
O1 O 0.2703(3) 0.1332(2) 0.01845(8) 0.0573(4) Uani 1 1 d . . . . .
O3 O 0.7055(3) 0.3438(2) 0.08172(8) 0.0575(4) Uani 1 1 d . . . . .
O4 O 0.6165(3) 0.3007(2) -0.04369(9) 0.0581(5) Uani 1 1 d . . . . .
H4O H 0.538(5) 0.252(4) -0.0074(17) 0.087 Uiso 1 1 d . U . . .
N1 N -0.0056(4) -0.0035(3) 0.08634(9) 0.0473(4) Uani 1 1 d . . . . .
H1N H -0.120(5) -0.051(3) 0.0499(13) 0.071 Uiso 1 1 d . U . . .
H2N H 0.440(5) 0.218(4) 0.1317(14) 0.071 Uiso 1 1 d . U . . .
N2 N 0.2990(4) 0.1421(2) 0.13027(9) 0.0485(5) Uani 1 1 d . . . . .
C1 C 0.1970(4) 0.0941(3) 0.07312(11) 0.0461(5) Uani 1 1 d . . . . .
C3 C 0.1599(4) 0.0774(3) 0.18050(11) 0.0440(5) Uani 1 1 d . . . . .
C4 C 0.1815(4) 0.0922(3) 0.24603(11) 0.0499(5) Uani 1 1 d . . . . .
H4 H 0.309863 0.154174 0.264593 0.060 Uiso 1 1 calc R U . . .
C5 C 0.0050(5) 0.0115(3) 0.28296(11) 0.0515(6) Uani 1 1 d . . . . .
H5 H 0.013851 0.020063 0.327321 0.062 Uiso 1 1 calc R U . . .
C6 C -0.1865(5) -0.0829(3) 0.25530(12) 0.0528(6) Uani 1 1 d . . . . .
H6 H -0.301055 -0.137301 0.281549 0.063 Uiso 1 1 calc R U . . .
C7 C -0.2091(5) -0.0969(3) 0.18942(11) 0.0515(6) Uani 1 1 d . . . . .
H7 H -0.337730 -0.158588 0.170836 0.062 Uiso 1 1 calc R U . . .
C8 C -0.0332(4) -0.0157(3) 0.15253(11) 0.0432(5) Uani 1 1 d . . . . .
C9 C 1.0433(4) 0.5267(3) 0.06752(11) 0.0493(5) Uani 1 1 d . . . . .
H9 H 1.067131 0.543079 0.111198 0.059 Uiso 1 1 calc R U . . .
C10 C 0.8444(4) 0.4200(3) 0.04557(11) 0.0438(5) Uani 1 1 d . . . . .
C11 C 0.8058(4) 0.3976(3) -0.02557(10) 0.0441(5) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0015 0.0009 '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 0.0030 0.0019 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0056 0.0036 '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
_geom_angle_publ_flag
C11 O4 H4O 110.5(18) . . ?
C1 N1 C8 109.05(19) . . ?
C1 N1 H1N 121.7(14) . . ?
C8 N1 H1N 129.1(14) . . ?
C1 N2 C3 110.05(19) . . ?
C1 N2 H2N 120.8(18) . . ?
C3 N2 H2N 129.0(18) . . ?
O1 C1 N1 125.4(2) . . ?
O1 C1 N2 127.1(2) . . ?
N1 C1 N2 107.42(19) . . ?
C4 C3 N2 132.4(2) . . ?
C4 C3 C8 121.4(2) . . ?
N2 C3 C8 106.16(19) . . ?
C3 C4 C5 117.3(2) . . ?
C3 C4 H4 121.3 . . ?
C5 C4 H4 121.3 . . ?
C4 C5 C6 121.5(2) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C7 C6 C5 121.1(2) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C8 C7 C6 117.3(2) . . ?
C8 C7 H7 121.3 . . ?
C6 C7 H7 121.3 . . ?
C7 C8 N1 131.4(2) . . ?
C7 C8 C3 121.3(2) . . ?
N1 C8 C3 107.3(2) . . ?
C11 C9 C10 120.5(2) 3_765 . ?
C11 C9 H9 119.8 3_765 . ?
C10 C9 H9 119.8 . . ?
O3 C10 C9 123.3(2) . . ?
O3 C10 C11 117.8(2) . . ?
C9 C10 C11 118.9(2) . . ?
O4 C11 C9 122.5(2) . 3_765 ?
O4 C11 C10 116.86(19) . . ?
C9 C11 C10 120.6(2) 3_765 . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.247(3) . ?
O3 C10 1.223(3) . ?
O4 C11 1.329(3) . ?
O4 H4O 0.95(3) . ?
N1 C1 1.363(3) . ?
N1 C8 1.394(3) . ?
N1 H1N 1.05(3) . ?
N2 C1 1.366(3) . ?
N2 C3 1.386(3) . ?
N2 H2N 0.97(3) . ?
C3 C4 1.378(3) . ?
C3 C8 1.399(3) . ?
C4 C5 1.378(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.396(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.385(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.377(3) . ?
C7 H7 0.9300 . ?
C9 C11 1.337(3) 3_765 ?
C9 C10 1.439(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.510(3) . ?
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
N2 H2N O3 0.97(3) 2.03(3) 2.890(3) 147(2) . yes
O4 H4O O1 0.95(3) 1.80(3) 2.627(2) 144(3) . yes
O4 H4O O3 0.95(3) 2.19(3) 2.683(2) 111(2) . yes
N1 H1N O1 1.05(3) 1.76(3) 2.802(2) 171(2) 3 yes
C5 H5 O3 0.93 2.65 3.331(3) 130.7 2_545 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
_geom_torsion_publ_flag
C8 N1 C1 O1 -178.3(2) . . . . ?
C8 N1 C1 N2 0.6(3) . . . . ?
C3 N2 C1 O1 178.0(2) . . . . ?
C3 N2 C1 N1 -0.8(2) . . . . ?
C1 N2 C3 C4 -178.4(3) . . . . ?
C1 N2 C3 C8 0.8(2) . . . . ?
N2 C3 C4 C5 179.1(2) . . . . ?
C8 C3 C4 C5 0.0(4) . . . . ?
C3 C4 C5 C6 0.6(4) . . . . ?
C4 C5 C6 C7 -1.0(4) . . . . ?
C5 C6 C7 C8 0.8(4) . . . . ?
C6 C7 C8 N1 -179.1(2) . . . . ?
C6 C7 C8 C3 -0.2(4) . . . . ?
C1 N1 C8 C7 178.9(2) . . . . ?
C1 N1 C8 C3 -0.1(3) . . . . ?
C4 C3 C8 C7 -0.2(4) . . . . ?
N2 C3 C8 C7 -179.5(2) . . . . ?
C4 C3 C8 N1 178.9(2) . . . . ?
N2 C3 C8 N1 -0.4(3) . . . . ?
C11 C9 C10 O3 177.8(2) 3_765 . . . ?
C11 C9 C10 C11 -1.1(4) 3_765 . . . ?
O3 C10 C11 O4 2.4(3) . . . . ?
C9 C10 C11 O4 -178.59(19) . . . . ?
O3 C10 C11 C9 -177.8(2) . . . 3_765 ?
C9 C10 C11 C9 1.1(4) . . . 3_765 ?
