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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/7/24/10/7241093.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_7241093
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 H2 Cl2 O4, 2(C8 H6 N2 O2)'
_chemical_formula_sum            'C22 H14 Cl2 N4 O8'
_chemical_formula_weight         533.27
_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     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2020-07-14
_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                65.883(8)
_cell_angle_beta                 86.445(9)
_cell_angle_gamma                78.351(8)
_cell_formula_units_Z            1
_cell_length_a                   4.7921(5)
_cell_length_b                   11.1245(12)
_cell_length_c                   11.2988(13)
_cell_measurement_reflns_used    12065
_cell_measurement_temperature    295(1)
_cell_measurement_theta_max      27.85
_cell_measurement_theta_min      2.66
_cell_volume                     538.29(11)
_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 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
1157 frames, 50 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  0.0415
_diffrn_reflns_av_unetI/netI     0.0376
_diffrn_reflns_Laue_measured_fraction_full 0.998
_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       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15290
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        19.664
_diffrn_reflns_theta_max         22.499
_diffrn_reflns_theta_min         2.659
_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    0.194
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6536
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'X-AREA 1.86 (Stoe & Cie, 2018)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.645
_exptl_crystal_description       plate
_exptl_crystal_F_000             272
_exptl_crystal_recrystallization_method
;
Re-cristallisation from solvent: Acetonitrile
;
_exptl_crystal_size_max          0.398
_exptl_crystal_size_mid          0.146
_exptl_crystal_size_min          0.062
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.894
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2879
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.894
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0351
_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/[σ²(Fo²)+(0.0518P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0852
_refine_ls_wR_factor_ref         0.0910
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1984
_reflns_number_total             2879
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ce01056a2.cif
_cod_data_source_block           I
_cod_database_code               7241093
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.927
_shelx_estimated_absorpt_t_max   0.988
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
Cl1 Cl 0.52859(8) 0.37846(5) 0.87525(4) 0.04315(13) Uani 1 1 d . . . . .
O1 O 0.3204(2) 0.41633(10) 0.43342(12) 0.0404(3) Uani 1 1 d . . . . .
O2 O 0.3204(2) 0.17092(11) 0.43399(11) 0.0382(3) Uani 1 1 d . . . . .
N1 N 0.6917(3) 0.32450(12) 0.57831(13) 0.0319(3) Uani 1 1 d . . . . .
N2 N 0.6841(3) 0.07859(13) 0.58278(14) 0.0345(3) Uani 1 1 d . . . . .
C1 C 0.4949(3) 0.31902(14) 0.50219(15) 0.0306(3) Uani 1 1 d . . . . .
C2 C 0.4932(3) 0.18215(14) 0.50370(15) 0.0309(3) Uani 1 1 d . . . . .
C3 C 0.8714(3) 0.08705(15) 0.66750(15) 0.0318(3) Uani 1 1 d . . . . .
C4 C 1.0508(4) -0.02603(16) 0.75312(18) 0.0422(4) Uani 1 1 d . . . . .
H4 H 1.050735 -0.110088 0.754274 0.051 Uiso 1 1 calc R U . . .
C5 C 1.2290(4) -0.01275(18) 0.83635(19) 0.0467(4) Uani 1 1 d . . . . .
H5 H 1.345888 -0.088584 0.895234 0.056 Uiso 1 1 calc R U . . .
C6 C 1.2356(4) 0.11281(18) 0.83317(18) 0.0440(4) Uani 1 1 d . . . . .
H6 H 1.358116 0.120709 0.889151 0.053 Uiso 1 1 calc R U . . .
C7 C 1.0610(3) 0.22567(16) 0.74727(17) 0.0360(3) Uani 1 1 d . . . . .
H7 H 1.066973 0.309761 0.744674 0.043 Uiso 1 1 calc R U . . .
C8 C 0.8762(3) 0.21357(14) 0.66456(15) 0.0299(3) Uani 1 1 d . . . . .
O4 O 0.0737(3) 0.61396(14) 0.73596(12) 0.0476(3) Uani 1 1 d . . . . .
O3 O 0.3739(3) 0.29037(13) 1.15084(13) 0.0556(4) Uani 1 1 d . . . . .
C11 C 0.0478(3) 0.55541(16) 0.86264(15) 0.0336(3) Uani 1 1 d . . . . .
C10 C 0.2385(3) 0.44921(15) 0.93915(16) 0.0320(3) Uani 1 1 d . . . . .
C9 C 0.2069(3) 0.38654(16) 1.07880(16) 0.0346(3) Uani 1 1 d . . . . .
H1N H 0.701(4) 0.407(2) 0.5737(18) 0.052 Uiso 1 1 d . U . . .
H2N H 0.679(4) -0.002(2) 0.5824(18) 0.052 Uiso 1 1 d . U . . .
H4O H -0.071(4) 0.665(2) 0.704(2) 0.052 Uiso 1 1 d . U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0015 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'
Cl Cl 0.0998 0.0984 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
3 -1 -7 0.0430
-4 1 8 0.0190
-4 1 0 0.1350
-2 1 -8 0.1930
3 -1 6 0.2050
1 10 4 0.0760
-1 -11 -4 0.0700
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
C1 N1 C8 124.87(13) . . ?
C1 N1 H1N 116.8(12) . . ?
C8 N1 H1N 118.3(12) . . ?
C2 N2 C3 124.71(13) . . ?
C2 N2 H2N 115.5(12) . . ?
C3 N2 H2N 119.7(12) . . ?
O1 C1 N1 124.18(13) . . ?
O1 C1 C2 119.27(13) . . ?
N1 C1 C2 116.55(13) . . ?
O2 C2 N2 123.48(13) . . ?
O2 C2 C1 119.65(13) . . ?
N2 C2 C1 116.87(13) . . ?
C4 C3 N2 121.70(14) . . ?
C4 C3 C8 120.00(15) . . ?
N2 C3 C8 118.31(13) . . ?
C5 C4 C3 119.52(15) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 C6 120.64(16) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C7 C6 C5 120.16(16) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C6 C7 C8 119.85(15) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
C7 C8 N1 121.77(13) . . ?
C7 C8 C3 119.81(14) . . ?
N1 C8 C3 118.42(13) . . ?
C11 O4 H4O 110.0(15) . . ?
O4 C11 C10 122.69(14) . . ?
O4 C11 C9 117.25(14) . 2_567 ?
C10 C11 C9 120.06(14) . 2_567 ?
C11 C10 C9 121.82(13) . . ?
C11 C10 Cl1 121.30(12) . . ?
C9 C10 Cl1 116.87(11) . . ?
O3 C9 C10 123.69(14) . . ?
O3 C9 C11 118.19(15) . 2_567 ?
C10 C9 C11 118.12(13) . 2_567 ?
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
Cl1 C10 1.7237(14) . ?
O1 C1 1.2256(18) . ?
O2 C2 1.2349(18) . ?
N1 C1 1.3415(19) . ?
N1 C8 1.3920(19) . ?
N1 H1N 0.91(2) . ?
N2 C2 1.3405(19) . ?
N2 C3 1.395(2) . ?
N2 H2N 0.90(2) . ?
C1 C2 1.517(2) . ?
C3 C4 1.389(2) . ?
C3 C8 1.399(2) . ?
C4 C5 1.378(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.389(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.378(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.389(2) . ?
C7 H7 0.9300 . ?
O4 C11 1.3180(19) . ?
O4 H4O 0.80(2) . ?
O3 C9 1.2128(18) . ?
C11 C10 1.344(2) . ?
C11 C9 1.508(2) 2_567 ?
C10 C9 1.454(2) . ?
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
N1 H1N O1 0.91(2) 1.91(2) 2.8203(16) 174.1(17) 2_666 yes
N2 H2N O2 0.90(2) 1.96(2) 2.8628(17) 175.0(18) 2_656 yes
O4 H4O O1 0.80(2) 2.54(2) 2.9284(17) 111.6(18) 2_566 yes
O4 H4O O2 0.80(2) 2.05(2) 2.8017(17) 156(2) 2_566 yes
O4 H4O O3 0.80(2) 2.27(2) 2.6867(18) 113.4(18) 2_567 yes
N1 H1N O1 0.91(2) 1.91(2) 2.8203(16) 174.1(17) 2_666 yes
N2 H2N O2 0.90(2) 1.96(2) 2.8628(17) 175.0(18) 2_656 yes
O4 H4O O1 0.80(2) 2.54(2) 2.9284(17) 111.6(18) 2_566 yes
O4 H4O O2 0.80(2) 2.05(2) 2.8017(17) 156(2) 2_566 yes
O4 H4O O3 0.80(2) 2.27(2) 2.6867(18) 113.4(18) 2_567 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 174.64(15) . . . . ?
C8 N1 C1 C2 -5.2(2) . . . . ?
C3 N2 C2 O2 -176.45(15) . . . . ?
C3 N2 C2 C1 3.5(2) . . . . ?
O1 C1 C2 O2 1.4(2) . . . . ?
N1 C1 C2 O2 -178.74(14) . . . . ?
O1 C1 C2 N2 -178.52(14) . . . . ?
N1 C1 C2 N2 1.3(2) . . . . ?
C2 N2 C3 C4 175.59(15) . . . . ?
C2 N2 C3 C8 -4.5(2) . . . . ?
N2 C3 C4 C5 -178.98(16) . . . . ?
C8 C3 C4 C5 1.2(3) . . . . ?
C3 C4 C5 C6 -1.6(3) . . . . ?
C4 C5 C6 C7 0.7(3) . . . . ?
C5 C6 C7 C8 0.6(3) . . . . ?
C6 C7 C8 N1 178.55(15) . . . . ?
C6 C7 C8 C3 -1.0(2) . . . . ?
C1 N1 C8 C7 -175.28(14) . . . . ?
C1 N1 C8 C3 4.3(2) . . . . ?
C4 C3 C8 C7 0.1(2) . . . . ?
N2 C3 C8 C7 -179.74(14) . . . . ?
C4 C3 C8 N1 -179.44(14) . . . . ?
N2 C3 C8 N1 0.7(2) . . . . ?
O4 C11 C10 C9 179.66(15) . . . . ?
C9 C11 C10 C9 0.4(2) 2_567 . . . ?
O4 C11 C10 Cl1 -1.9(2) . . . . ?
C9 C11 C10 Cl1 178.83(11) 2_567 . . . ?
C11 C10 C9 O3 179.72(16) . . . . ?
Cl1 C10 C9 O3 1.2(2) . . . . ?
C11 C10 C9 C11 -0.4(2) . . . 2_567 ?
Cl1 C10 C9 C11 -178.89(11) . . . 2_567 ?
