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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/7/24/10/7241096.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_7241096
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(C7 H6 N2 O)'
_chemical_formula_sum            'C20 H14 Cl2 N4 O6'
_chemical_formula_weight         477.25
_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   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-10-17
_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                 99.316(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.4521(5)
_cell_length_b                   5.1303(2)
_cell_length_c                   23.1482(14)
_cell_measurement_reflns_used    15454
_cell_measurement_temperature    295(1)
_cell_measurement_theta_max      26.44
_cell_measurement_theta_min      2.56
_cell_volume                     990.51(9)
_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 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
1168 frames, 50-70 s/frame, 1 deg./frame, detector distance = 45 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  0.0449
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            20107
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        19.664
_diffrn_reflns_theta_max         20.996
_diffrn_reflns_theta_min         2.618
_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    0.201
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.4915
_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    1.600
_exptl_crystal_description       prism
_exptl_crystal_F_000             488
_exptl_crystal_recrystallization_method
;
Re-cristallisation from solvent: Acetonitrile
;
_exptl_crystal_size_max          0.201
_exptl_crystal_size_mid          0.138
_exptl_crystal_size_min          0.075
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2160
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0364
_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)+(0.0596P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0987
_refine_ls_wR_factor_ref         0.1037
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1600
_reflns_number_total             2160
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ce01056a2.cif
_cod_data_source_block           II
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7241096
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.961
_shelx_estimated_absorpt_t_max   0.985
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
Cl1 Cl 0.54056(7) 0.18828(10) 0.63114(2) 0.05506(19) Uani 1 1 d . . . . .
O1 O 0.14041(19) 0.2726(3) 0.51833(7) 0.0581(4) Uani 1 1 d . . . . .
O3 O 0.34695(18) -0.2487(3) 0.57467(6) 0.0546(4) Uani 1 1 d . . . . .
O4 O 0.69292(19) 0.4192(3) 0.53684(7) 0.0517(4) Uani 1 1 d . . . . .
H4O H 0.734(3) 0.484(5) 0.5108(12) 0.070(8) Uiso 1 1 d . . . . .
N1 N 0.0044(2) 0.0251(3) 0.57829(8) 0.0482(4) Uani 1 1 d . . . . .
H1 H -0.041(3) -0.081(4) 0.5505(10) 0.049(6) Uiso 1 1 d . . . . .
N2 N 0.1411(2) 0.3563(3) 0.61747(9) 0.0524(5) Uani 1 1 d . . . . .
H2 H 0.201(3) 0.472(4) 0.6213(10) 0.048(6) Uiso 1 1 d . . . . .
C1 C 0.0990(2) 0.2241(4) 0.56670(10) 0.0481(5) Uani 1 1 d . . . . .
C3 C 0.0760(2) 0.2379(3) 0.66247(10) 0.0468(5) Uani 1 1 d . . . . .
C4 C 0.0834(3) 0.2950(4) 0.72094(11) 0.0552(5) Uani 1 1 d . . . . .
C5 C -0.0012(3) 0.1356(4) 0.75330(11) 0.0585(6) Uani 1 1 d . . . . .
C6 C -0.0903(3) -0.0723(4) 0.72783(11) 0.0577(6) Uani 1 1 d . . . . .
C7 C -0.0973(3) -0.1319(4) 0.66898(11) 0.0528(5) Uani 1 1 d . . . . .
C8 C -0.0128(2) 0.0276(3) 0.63661(9) 0.0455(5) Uani 1 1 d . . . . .
C9 C 0.4191(2) -0.1305(3) 0.54157(8) 0.0405(4) Uani 1 1 d . . . . .
C10 C 0.5234(2) 0.0901(3) 0.55979(8) 0.0409(4) Uani 1 1 d . . . . .
C11 C 0.6003(2) 0.2152(3) 0.52124(8) 0.0411(4) Uani 1 1 d . . . . .
H4 H 0.145(3) 0.425(4) 0.7403(10) 0.060(6) Uiso 1 1 d . . . . .
H5 H -0.004(3) 0.169(5) 0.7903(12) 0.068(7) Uiso 1 1 d . . . . .
H6 H -0.150(3) -0.181(5) 0.7505(12) 0.072(7) Uiso 1 1 d . . . . .
H7 H -0.163(3) -0.268(4) 0.6491(10) 0.055(6) Uiso 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'
Cl Cl 0.0998 0.0984 '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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 -2 9 0.0380
1 2 -9 0.0370
-1 2 9 0.0560
3 -1 -5 0.0630
1 -2 -9 0.0820
-3 -1 -5 0.0910
7 1 4 0.1090
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 115.3(18) . . ?
C1 N1 C8 110.30(18) . . ?
C1 N1 H1 121.7(14) . . ?
C8 N1 H1 127.9(14) . . ?
C1 N2 C3 110.53(17) . . ?
C1 N2 H2 123.9(17) . . ?
C3 N2 H2 125.3(17) . . ?
O1 C1 N1 126.1(2) . . ?
O1 C1 N2 127.25(18) . . ?
N1 C1 N2 106.69(19) . . ?
C4 C3 C8 121.54(19) . . ?
C4 C3 N2 132.97(19) . . ?
C8 C3 N2 105.47(18) . . ?
C3 C4 C5 117.5(2) . . ?
C3 C4 H4 124.5(15) . . ?
C5 C4 H4 117.9(15) . . ?
C6 C5 C4 121.3(2) . . ?
C6 C5 H5 118.0(17) . . ?
C4 C5 H5 120.7(17) . . ?
C5 C6 C7 121.5(2) . . ?
C5 C6 H6 120.8(15) . . ?
C7 C6 H6 117.7(15) . . ?
C8 C7 C6 117.2(2) . . ?
C8 C7 H7 118.7(14) . . ?
C6 C7 H7 123.9(14) . . ?
N1 C8 C7 132.0(2) . . ?
N1 C8 C3 106.99(16) . . ?
C7 C8 C3 121.0(2) . . ?
O3 C9 C10 123.20(18) . . ?
O3 C9 C11 118.60(17) . 3_656 ?
C10 C9 C11 118.20(15) . 3_656 ?
C11 C10 C9 120.85(18) . . ?
C11 C10 Cl1 121.61(15) . . ?
C9 C10 Cl1 117.52(13) . . ?
O4 C11 C10 121.59(18) . . ?
O4 C11 C9 117.45(15) . 3_656 ?
C10 C11 C9 120.95(17) . 3_656 ?
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 1.710(2) . ?
O1 C1 1.251(3) . ?
O3 C9 1.216(2) . ?
O4 C11 1.321(2) . ?
O4 H4O 0.81(3) . ?
N1 C1 1.350(2) . ?
N1 C8 1.381(3) . ?
N1 H1 0.88(2) . ?
N2 C1 1.354(3) . ?
N2 C3 1.394(3) . ?
N2 H2 0.77(2) . ?
C3 C4 1.376(3) . ?
C3 C8 1.393(3) . ?
C4 C5 1.384(3) . ?
C4 H4 0.92(2) . ?
C5 C6 1.381(3) . ?
C5 H5 0.88(3) . ?
C6 C7 1.388(3) . ?
C6 H6 0.96(3) . ?
C7 C8 1.384(3) . ?
C7 H7 0.96(2) . ?
C9 C10 1.454(3) . ?
C9 C11 1.501(3) 3_656 ?
C10 C11 1.349(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 H2 O3 0.77(2) 2.28(2) 2.945(2) 145(2) 1_565 yes
N1 H1 O1 0.88(2) 1.94(2) 2.819(2) 171.7(19) 3_556 yes
O4 H4O O1 0.81(3) 1.84(3) 2.588(2) 153(3) 3_666 yes
C6 H6 Cl1 0.96(3) 2.83(3) 3.449(2) 123.1(19) 2_546 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 178.52(19) . . . . ?
C8 N1 C1 N2 -0.7(2) . . . . ?
C3 N2 C1 O1 -177.8(2) . . . . ?
C3 N2 C1 N1 1.4(2) . . . . ?
C1 N2 C3 C4 179.9(2) . . . . ?
C1 N2 C3 C8 -1.5(2) . . . . ?
C8 C3 C4 C5 -0.1(3) . . . . ?
N2 C3 C4 C5 178.3(2) . . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
C4 C5 C6 C7 0.7(4) . . . . ?
C5 C6 C7 C8 -0.8(3) . . . . ?
C1 N1 C8 C7 179.5(2) . . . . ?
C1 N1 C8 C3 -0.2(2) . . . . ?
C6 C7 C8 N1 -179.4(2) . . . . ?
C6 C7 C8 C3 0.3(3) . . . . ?
C4 C3 C8 N1 179.86(19) . . . . ?
N2 C3 C8 N1 1.0(2) . . . . ?
C4 C3 C8 C7 0.1(3) . . . . ?
N2 C3 C8 C7 -178.74(18) . . . . ?
O3 C9 C10 C11 -179.76(18) . . . . ?
C11 C9 C10 C11 0.1(3) 3_656 . . . ?
O3 C9 C10 Cl1 -1.2(3) . . . . ?
C11 C9 C10 Cl1 178.62(13) 3_656 . . . ?
C9 C10 C11 O4 178.65(16) . . . . ?
Cl1 C10 C11 O4 0.2(3) . . . . ?
C9 C10 C11 C9 -0.1(3) . . . 3_656 ?
Cl1 C10 C11 C9 -178.56(13) . . . 3_656 ?
