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#$Date: 2023-11-06 09:29:46 +0200 (Mon, 06 Nov 2023) $
#$Revision: 287350 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/74/7247448.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_7247448
loop_
_publ_author_name
'Dubey, Ritesh'
'Singh, Sandeep'
_publ_section_title
;
 Dichlorosubstitution as a steering tool in hydrogen bonded cocrystals:
 the nature of rigid and flexible coformers in crystal structures
;
_journal_issue                   40
_journal_name_full               CrystEngComm
_journal_page_first              5697
_journal_page_last               5705
_journal_paper_doi               10.1039/D3CE00672G
_journal_volume                  25
_journal_year                    2023
_chemical_formula_sum            'C22 H16 Cl4 N2 O2'
_chemical_formula_weight         482.17
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-06-27 deposited with the CCDC.	2023-08-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.64(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.789(7)
_cell_length_b                   14.243(19)
_cell_length_c                   12.602(16)
_cell_measurement_reflns_used    809
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.8
_cell_measurement_theta_min      3.3
_cell_volume                     1027(2)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0523
_diffrn_reflns_av_unetI/netI     0.0447
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10520
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         3.270
_exptl_absorpt_coefficient_mu    0.599
_exptl_crystal_density_diffrn    1.559
_exptl_crystal_description       Plate
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         2349
_refine_ls_number_restraints     183
_refine_ls_restrained_S_all      0.991
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0320
_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)+(0.0362P)²+0.3610P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0829
_refine_ls_wR_factor_ref         0.0849
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2149
_reflns_number_total             2349
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ce00672g1.cif
_cod_data_source_block           datam_CCDC6
_cod_depositor_comments
'Adding full bibliography for 7247442--7247454.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7247448
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.865
_shelx_estimated_absorpt_t_max   0.942
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
C1 C 0.4324(2) 0.58052(10) 0.30853(11) 0.0187(3) Uani 1 1 d . U . . .
C2 C 0.6219(2) 0.54125(10) 0.26845(11) 0.0187(3) Uani 1 1 d . U . . .
C3 C 0.6787(3) 0.44756(10) 0.28381(12) 0.0228(3) Uani 1 1 d . U . . .
H3 H 0.809629 0.422610 0.256068 0.027 Uiso 1 1 calc R U . . .
C4 C 0.5467(3) 0.38987(10) 0.33916(13) 0.0250(3) Uani 1 1 d . U . . .
H4 H 0.583107 0.325134 0.349191 0.030 Uiso 1 1 calc R U . . .
C5 C 0.3601(3) 0.42935(10) 0.37947(11) 0.0217(3) Uani 1 1 d . U . . .
C6 C 0.3009(2) 0.52293(10) 0.36539(11) 0.0204(3) Uani 1 1 d . U . . .
H6 H 0.171331 0.547707 0.394340 0.025 Uiso 1 1 calc R U . . .
C7 C 0.2820(3) 0.82245(10) 0.46949(12) 0.0239(3) Uani 1 1 d . U . . .
H7 H 0.430648 0.794543 0.491231 0.029 Uiso 1 1 calc R U . . .
C8 C 0.2400(3) 0.90982(10) 0.51064(12) 0.0222(3) Uani 1 1 d . U . . .
H8 H 0.357129 0.940112 0.559725 0.027 Uiso 1 1 calc R U . . .
C9 C 0.0256(2) 0.95283(9) 0.47968(10) 0.0156(3) Uani 1 1 d . U . . .
C10 C -0.1365(2) 0.90323(10) 0.40904(12) 0.0200(3) Uani 1 1 d . U . . .
H10 H -0.286288 0.929470 0.385555 0.024 Uiso 1 1 calc R U . . .
C11 C -0.0809(3) 0.81556(10) 0.37255(12) 0.0223(3) Uani 1 1 d . U . . .
H11 H -0.195878 0.782732 0.324885 0.027 Uiso 1 1 calc R U . . .
N1 N 0.1265(2) 0.77529(8) 0.40130(10) 0.0213(3) Uani 1 1 d . U . . .
O1 O 0.38654(19) 0.67179(7) 0.28909(9) 0.0255(2) Uani 1 1 d . U . . .
H1 H 0.282(4) 0.6894(6) 0.3238(16) 0.038 Uiso 1 1 calc R U . . .
Cl1 Cl 0.78854(6) 0.61289(2) 0.19851(3) 0.02438(12) Uani 1 1 d . U . . .
Cl2 Cl 0.19202(7) 0.35821(3) 0.45035(3) 0.03083(13) Uani 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 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
O1 C1 C6 123.88(13) . . ?
O1 C1 C2 117.91(13) . . ?
C6 C1 C2 118.21(15) . . ?
C3 C2 C1 121.42(14) . . ?
C3 C2 Cl1 120.08(12) . . ?
C1 C2 Cl1 118.49(13) . . ?
C4 C3 C2 120.52(14) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 117.81(15) . . ?
C3 C4 H4 121.1 . . ?
C5 C4 H4 121.1 . . ?
C4 C5 C6 122.60(14) . . ?
C4 C5 Cl2 118.70(14) . . ?
C6 C5 Cl2 118.71(13) . . ?
C5 C6 C1 119.44(14) . . ?
C5 C6 H6 120.3 . . ?
C1 C6 H6 120.3 . . ?
N1 C7 C8 123.81(15) . . ?
N1 C7 H7 118.1 . . ?
C8 C7 H7 118.1 . . ?
C7 C8 C9 119.49(14) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 H8 120.3 . . ?
C10 C9 C8 116.53(14) . . ?
C10 C9 C9 122.16(16) . 3_576 ?
C8 C9 C9 121.31(16) . 3_576 ?
C11 C10 C9 120.27(14) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
N1 C11 C10 122.90(14) . . ?
N1 C11 H11 118.5 . . ?
C10 C11 H11 118.5 . . ?
C7 N1 C11 116.99(14) . . ?
C1 O1 H1 109.5 . . ?
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
C1 O1 1.342(2) . ?
C1 C6 1.389(2) . ?
C1 C2 1.392(2) . ?
C2 C3 1.381(3) . ?
C2 Cl1 1.7332(19) . ?
C3 C4 1.380(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.381(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.381(3) . ?
C5 Cl2 1.742(2) . ?
C6 H6 0.9500 . ?
C7 N1 1.330(2) . ?
C7 C8 1.384(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.387(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.386(2) . ?
C9 C9 1.484(3) 3_576 ?
C10 C11 1.385(2) . ?
C10 H10 0.9500 . ?
C11 N1 1.331(2) . ?
C11 H11 0.9500 . ?
O1 H1 0.84(2) . ?
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
O1 C1 C2 C3 -179.14(13) . . . . ?
C6 C1 C2 C3 0.3(2) . . . . ?
O1 C1 C2 Cl1 1.12(18) . . . . ?
C6 C1 C2 Cl1 -179.40(10) . . . . ?
C1 C2 C3 C4 0.4(2) . . . . ?
Cl1 C2 C3 C4 -179.83(11) . . . . ?
C2 C3 C4 C5 -0.9(2) . . . . ?
C3 C4 C5 C6 0.7(2) . . . . ?
C3 C4 C5 Cl2 -179.60(11) . . . . ?
C4 C5 C6 C1 0.1(2) . . . . ?
Cl2 C5 C6 C1 -179.64(11) . . . . ?
O1 C1 C6 C5 178.87(13) . . . . ?
C2 C1 C6 C5 -0.6(2) . . . . ?
N1 C7 C8 C9 -0.6(2) . . . . ?
C7 C8 C9 C10 0.9(2) . . . . ?
C7 C8 C9 C9 -178.94(15) . . . 3_576 ?
C8 C9 C10 C11 -0.3(2) . . . . ?
C9 C9 C10 C11 179.59(15) 3_576 . . . ?
C9 C10 C11 N1 -0.8(2) . . . . ?
C8 C7 N1 C11 -0.4(2) . . . . ?
C10 C11 N1 C7 1.1(2) . . . . ?
