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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/7/24/74/7247447.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_7247447
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 2yn'
_space_group_name_H-M_alt        'P 1 21/n 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                 104.972(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.3339(14)
_cell_length_b                   7.2993(10)
_cell_length_c                   14.5440(19)
_cell_measurement_reflns_used    9438
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.6
_cell_measurement_theta_min      3.1
_cell_volume                     1059.8(2)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_unetI/netI     0.0194
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10358
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         3.145
_exptl_absorpt_coefficient_mu    0.581
_exptl_crystal_density_diffrn    1.511
_exptl_crystal_description       Plate
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         2436
_refine_ls_number_restraints     183
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0343
_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)+(0.0411P)²+0.4455P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0840
_refine_ls_wR_factor_ref         0.0875
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2119
_reflns_number_total             2436
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ce00672g1.cif
_cod_data_source_block           datam_CCDC5
_cod_depositor_comments
'Adding full bibliography for 7247442--7247454.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7247447
_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   0.893
_shelx_estimated_absorpt_t_max   0.944
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
C1 C 0.37540(14) 0.2483(2) 0.16482(10) 0.0247(3) Uani 1 1 d . U . . .
C2 C 0.37778(15) 0.0724(2) 0.20260(10) 0.0268(3) Uani 1 1 d . U . . .
C3 C 0.26855(17) -0.0449(2) 0.17768(12) 0.0345(4) Uani 1 1 d . U . . .
H3 H 0.274047 -0.165058 0.203551 0.041 Uiso 1 1 calc R U . . .
C4 C 0.15209(18) 0.0144(3) 0.11509(13) 0.0400(4) Uani 1 1 d . U . . .
H4 H 0.076784 -0.064877 0.097977 0.048 Uiso 1 1 calc R U . . .
C5 C 0.14439(16) 0.1888(3) 0.07712(12) 0.0362(4) Uani 1 1 d . U . . .
H5 H 0.063756 0.230285 0.034572 0.043 Uiso 1 1 calc R U . . .
C6 C 0.25490(15) 0.3024(2) 0.10154(10) 0.0280(3) Uani 1 1 d . U . . .
C7 C 0.80444(16) 0.2485(2) 0.36033(11) 0.0326(3) Uani 1 1 d . U . . .
H7 H 0.795066 0.126597 0.336660 0.039 Uiso 1 1 calc R U . . .
C8 C 0.92124(15) 0.2942(2) 0.42752(11) 0.0300(3) Uani 1 1 d . U . . .
H8 H 0.989318 0.204944 0.448850 0.036 Uiso 1 1 calc R U . . .
C9 C 0.93842(14) 0.4714(2) 0.46365(10) 0.0243(3) Uani 1 1 d . U . . .
C10 C 0.83389(15) 0.5940(2) 0.42818(11) 0.0308(3) Uani 1 1 d . U . . .
H10 H 0.840575 0.717157 0.449960 0.037 Uiso 1 1 calc R U . . .
C11 C 0.72046(16) 0.5357(2) 0.36124(12) 0.0330(3) Uani 1 1 d . U . . .
H11 H 0.650340 0.621494 0.338558 0.040 Uiso 1 1 calc R U . . .
N1 N 0.70430(13) 0.36539(19) 0.32683(9) 0.0310(3) Uani 1 1 d . U . . .
O1 O 0.47814(11) 0.36644(15) 0.18424(8) 0.0318(3) Uani 1 1 d . U . . .
H1 H 0.5351(18) 0.3295(17) 0.2280(15) 0.048 Uiso 1 1 calc R U . . .
Cl1 Cl 0.52075(4) -0.00083(5) 0.28616(3) 0.03656(13) Uani 1 1 d . U . . .
Cl2 Cl 0.24259(4) 0.52284(6) 0.05569(3) 0.03937(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 C2 125.25(13) . . ?
O1 C1 C6 118.61(13) . . ?
C2 C1 C6 116.14(13) . . ?
C3 C2 C1 122.33(15) . . ?
C3 C2 Cl1 118.69(13) . . ?
C1 C2 Cl1 118.96(11) . . ?
C4 C3 C2 119.40(16) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 120.27(15) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C6 C5 C4 119.46(16) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C5 C6 C1 122.39(15) . . ?
C5 C6 Cl2 118.98(13) . . ?
C1 C6 Cl2 118.59(11) . . ?
N1 C7 C8 123.89(15) . . ?
N1 C7 H7 118.1 . . ?
C8 C7 H7 118.1 . . ?
C7 C8 C9 119.61(15) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
C8 C9 C10 116.48(13) . . ?
C8 C9 C9 122.10(17) . 3_766 ?
C10 C9 C9 121.41(17) . 3_766 ?
C11 C10 C9 119.85(15) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
N1 C11 C10 123.48(15) . . ?
N1 C11 H11 118.3 . . ?
C10 C11 H11 118.3 . . ?
C7 N1 C11 116.69(13) . . ?
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 1.3399(16) . ?
C1 C2 1.395(2) . ?
C1 C6 1.400(2) . ?
C2 C3 1.388(2) . ?
C2 Cl1 1.7371(16) . ?
C3 C4 1.378(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.382(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.381(2) . ?
C5 H5 0.9500 . ?
C6 Cl2 1.7339(16) . ?
C7 N1 1.333(2) . ?
C7 C8 1.383(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.390(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.395(2) . ?
C9 C9 1.489(3) 3_766 ?
C10 C11 1.383(2) . ?
C10 H10 0.9500 . ?
C11 N1 1.334(2) . ?
C11 H11 0.9500 . ?
O1 H1 0.79(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 -178.42(14) . . . . ?
C6 C1 C2 C3 1.4(2) . . . . ?
O1 C1 C2 Cl1 3.3(2) . . . . ?
C6 C1 C2 Cl1 -176.84(11) . . . . ?
C1 C2 C3 C4 -1.5(2) . . . . ?
Cl1 C2 C3 C4 176.80(13) . . . . ?
C2 C3 C4 C5 0.3(3) . . . . ?
C3 C4 C5 C6 0.8(3) . . . . ?
C4 C5 C6 C1 -0.8(2) . . . . ?
C4 C5 C6 Cl2 -178.42(13) . . . . ?
O1 C1 C6 C5 179.57(14) . . . . ?
C2 C1 C6 C5 -0.3(2) . . . . ?
O1 C1 C6 Cl2 -2.79(19) . . . . ?
C2 C1 C6 Cl2 177.35(11) . . . . ?
N1 C7 C8 C9 -0.1(3) . . . . ?
C7 C8 C9 C10 -0.3(2) . . . . ?
C7 C8 C9 C9 179.73(17) . . . 3_766 ?
C8 C9 C10 C11 0.5(2) . . . . ?
C9 C9 C10 C11 -179.47(17) 3_766 . . . ?
C9 C10 C11 N1 -0.5(3) . . . . ?
C8 C7 N1 C11 0.1(2) . . . . ?
C10 C11 N1 C7 0.1(2) . . . . ?
