#------------------------------------------------------------------------------
#$Date: 2023-11-06 09:29:46 +0200 (Mon, 06 Nov 2023) $
#$Revision: 287350 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/74/7247445.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_7247445
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           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/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                 98.486(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.809(3)
_cell_length_b                   3.8575(6)
_cell_length_c                   29.184(5)
_cell_measurement_reflns_used    10352
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.8
_cell_measurement_theta_min      3.2
_cell_volume                     2094.3(6)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.997
_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  0.0353
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            9003
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_min         3.308
_exptl_absorpt_coefficient_mu    0.588
_exptl_crystal_density_diffrn    1.529
_exptl_crystal_description       Plate
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         2377
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0362
_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)+(0.0380P)²+1.2452P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0790
_refine_ls_wR_factor_ref         0.0829
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1982
_reflns_number_total             2377
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ce00672g1.cif
_cod_data_source_block           datam_CCDC3
_cod_depositor_comments
'Adding full bibliography for 7247442--7247454.cif.'
_cod_original_cell_volume        2094.2(6)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7247445
_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   0.867
_shelx_estimated_absorpt_t_max   0.944
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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 0.66476(9) 0.6828(5) 0.61260(5) 0.0222(4) Uani 1 1 d . . . . .
C2 C 0.59689(8) 0.6449(4) 0.58635(6) 0.0201(3) Uani 1 1 d . . . . .
C3 C 0.58295(8) 0.7521(4) 0.54073(5) 0.0217(4) Uani 1 1 d . . . . .
H3 H 0.536340 0.726007 0.523456 0.026 Uiso 1 1 calc R U . . .
C4 C 0.63805(9) 0.8980(4) 0.52066(6) 0.0217(4) Uani 1 1 d . . . . .
C5 C 0.70605(9) 0.9377(5) 0.54538(6) 0.0240(4) Uani 1 1 d . . . . .
H5 H 0.743639 1.036405 0.531198 0.029 Uiso 1 1 calc R U . . .
C6 C 0.71853(9) 0.8314(5) 0.59112(6) 0.0252(4) Uani 1 1 d . . . . .
H6 H 0.765109 0.860813 0.608319 0.030 Uiso 1 1 calc R U . . .
C7 C 0.83661(9) 0.6618(5) 0.74201(6) 0.0303(4) Uani 1 1 d . . . . .
H7 H 0.799917 0.728277 0.759385 0.036 Uiso 1 1 calc R U . . .
C8 C 0.90695(9) 0.6660(5) 0.76389(6) 0.0252(4) Uani 1 1 d . . . . .
H8 H 0.917798 0.733139 0.795469 0.030 Uiso 1 1 calc R U . . .
C9 C 0.96173(8) 0.5709(4) 0.73916(5) 0.0208(4) Uani 1 1 d . . . . .
C10 C 0.94191(9) 0.4737(5) 0.69310(6) 0.0254(4) Uani 1 1 d . . . . .
H10 H 0.977439 0.407296 0.674808 0.031 Uiso 1 1 calc R U . . .
C11 C 0.87032(10) 0.4747(5) 0.67432(6) 0.0296(4) Uani 1 1 d . . . . .
H11 H 0.857841 0.404076 0.642975 0.035 Uiso 1 1 calc R U . . .
N1 N 0.81720(8) 0.5694(4) 0.69765(5) 0.0310(4) Uani 1 1 d . . . . .
O1 O 0.67476(7) 0.5727(4) 0.65715(4) 0.0309(3) Uani 1 1 d . . . . .
H1 H 0.7168(12) 0.584(6) 0.6675(4) 0.046 Uiso 1 1 calc R U . . .
Cl1 Cl 0.52773(2) 0.45934(12) 0.61139(2) 0.02653(13) Uani 1 1 d . . . . .
Cl2 Cl 0.62004(2) 1.03844(13) 0.46321(2) 0.03093(14) 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 0.0033 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 123.72(14) . . ?
O1 C1 C2 118.71(15) . . ?
C6 C1 C2 117.58(15) . . ?
C3 C2 C1 121.70(15) . . ?
C3 C2 Cl1 118.76(12) . . ?
C1 C2 Cl1 119.54(13) . . ?
C2 C3 C4 118.84(15) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C5 C4 C3 121.19(15) . . ?
C5 C4 Cl2 120.03(13) . . ?
C3 C4 Cl2 118.78(12) . . ?
C4 C5 C6 118.92(15) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C5 C6 C1 121.77(15) . . ?
C5 C6 H6 119.1 . . ?
C1 C6 H6 119.1 . . ?
N1 C7 C8 123.73(16) . . ?
N1 C7 H7 118.1 . . ?
C8 C7 H7 118.1 . . ?
C7 C8 C9 119.27(15) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 H8 120.4 . . ?
C8 C9 C10 117.29(15) . . ?
C8 C9 C9 121.64(17) . 2_756 ?
C10 C9 C9 121.07(17) . 2_756 ?
C11 C10 C9 119.37(15) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
N1 C11 C10 123.85(16) . . ?
N1 C11 H11 118.1 . . ?
C10 C11 H11 118.1 . . ?
C7 N1 C11 116.49(15) . . ?
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 1.3542(19) . ?
C1 C6 1.390(2) . ?
C1 C2 1.396(2) . ?
C2 C3 1.382(2) . ?
C2 Cl1 1.7376(16) . ?
C3 C4 1.383(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.381(2) . ?
C4 Cl2 1.7469(17) . ?
C5 C6 1.383(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 N1 1.340(2) . ?
C7 C8 1.382(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.392(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.392(2) . ?
C9 C9 1.485(3) 2_756 ?
C10 C11 1.377(2) . ?
C10 H10 0.9500 . ?
C11 N1 1.340(2) . ?
C11 H11 0.9500 . ?
O1 H1 0.80(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 179.91(16) . . . . ?
C6 C1 C2 C3 -0.3(3) . . . . ?
O1 C1 C2 Cl1 0.0(2) . . . . ?
C6 C1 C2 Cl1 179.78(14) . . . . ?
C1 C2 C3 C4 0.5(3) . . . . ?
Cl1 C2 C3 C4 -179.62(13) . . . . ?
C2 C3 C4 C5 0.0(3) . . . . ?
C2 C3 C4 Cl2 -179.19(13) . . . . ?
C3 C4 C5 C6 -0.5(3) . . . . ?
Cl2 C4 C5 C6 178.59(14) . . . . ?
C4 C5 C6 C1 0.7(3) . . . . ?
O1 C1 C6 C5 179.46(17) . . . . ?
C2 C1 C6 C5 -0.3(3) . . . . ?
N1 C7 C8 C9 0.2(3) . . . . ?
C7 C8 C9 C10 -0.3(3) . . . . ?
C7 C8 C9 C9 179.92(14) . . . 2_756 ?
C8 C9 C10 C11 -0.2(3) . . . . ?
C9 C9 C10 C11 179.55(13) 2_756 . . . ?
C9 C10 C11 N1 1.0(3) . . . . ?
C8 C7 N1 C11 0.5(3) . . . . ?
C10 C11 N1 C7 -1.1(3) . . . . ?
