#------------------------------------------------------------------------------
#$Date: 2023-11-06 09:29:46 +0200 (Mon, 06 Nov 2023) $
#$Revision: 287350 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/74/7247452.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_7247452
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            'C24 H16 Cl4 N2 O2'
_chemical_formula_weight         506.19
_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   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                85.572(6)
_cell_angle_beta                 79.226(6)
_cell_angle_gamma                71.653(5)
_cell_formula_units_Z            2
_cell_length_a                   7.9894(16)
_cell_length_b                   9.4955(19)
_cell_length_c                   15.762(3)
_cell_measurement_reflns_used    7444
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.6
_cell_measurement_theta_min      3.0
_cell_volume                     1114.8(4)
_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 0.996
_diffrn_measurement_device_type  'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0807
_diffrn_reflns_av_unetI/netI     0.1043
_diffrn_reflns_Laue_measured_fraction_full 0.998
_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       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11845
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.478
_diffrn_reflns_theta_min         3.024
_exptl_absorpt_coefficient_mu    0.557
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_description       Plate
_exptl_crystal_F_000             516
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         5112
_refine_ls_number_restraints     432
_refine_ls_restrained_S_all      0.979
_refine_ls_R_factor_all          0.1219
_refine_ls_R_factor_gt           0.0616
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0446P)²+0.2599P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1145
_refine_ls_wR_factor_ref         0.1343
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2953
_reflns_number_total             5112
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ce00672g1.cif
_cod_data_source_block           datam_CCDC10
_cod_depositor_comments
'Adding full bibliography for 7247442--7247454.cif.'
_cod_database_code               7247452
_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   0.788
_shelx_estimated_absorpt_t_max   0.946
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
C1 C 1.0024(4) 0.6738(4) 0.2662(2) 0.0218(7) Uani 1 1 d . U . . .
C2 C 1.1357(4) 0.5745(4) 0.2104(2) 0.0247(7) Uani 1 1 d . U . . .
C3 C 1.2497(4) 0.6226(4) 0.1464(2) 0.0271(8) Uani 1 1 d . U . . .
H3 H 1.337649 0.553003 0.108265 0.032 Uiso 1 1 calc R U . . .
C4 C 1.2368(5) 0.7706(4) 0.1376(2) 0.0304(8) Uani 1 1 d . U . . .
H4 H 1.315681 0.804374 0.094000 0.036 Uiso 1 1 calc R U . . .
C5 C 1.1070(5) 0.8687(4) 0.1933(2) 0.0281(8) Uani 1 1 d . U . . .
C6 C 0.9875(4) 0.8242(4) 0.2572(2) 0.0247(7) Uani 1 1 d . U . . .
H6 H 0.897641 0.894861 0.293910 0.030 Uiso 1 1 calc R U . . .
C7 C 0.6420(4) 0.7760(4) 0.1842(2) 0.0221(7) Uani 1 1 d . U . . .
C8 C 0.6729(5) 0.8545(4) 0.1070(2) 0.0277(8) Uani 1 1 d . U . . .
C9 C 0.7376(5) 0.7827(4) 0.0297(2) 0.0374(9) Uani 1 1 d . U . . .
H9 H 0.760679 0.837622 -0.021684 0.045 Uiso 1 1 calc R U . . .
C10 C 0.7696(5) 0.6311(4) 0.0260(2) 0.0371(9) Uani 1 1 d . U . . .
H10 H 0.812533 0.581326 -0.027436 0.045 Uiso 1 1 calc R U . . .
C11 C 0.7375(4) 0.5543(4) 0.1021(2) 0.0271(8) Uani 1 1 d . U . . .
C12 C 0.6768(4) 0.6235(4) 0.1799(2) 0.0234(7) Uani 1 1 d . U . . .
H12 H 0.658244 0.567016 0.231196 0.028 Uiso 1 1 calc R U . . .
C13 C 0.8111(5) 0.8737(4) 0.4857(2) 0.0317(8) Uani 1 1 d . U . . .
H13 H 0.905901 0.892185 0.444905 0.038 Uiso 1 1 calc R U . . .
C14 C 0.7924(5) 0.9129(4) 0.5711(2) 0.0356(9) Uani 1 1 d . U . . .
H14 H 0.872531 0.957195 0.587573 0.043 Uiso 1 1 calc R U . . .
C15 C 0.6578(5) 0.8868(4) 0.6308(2) 0.0320(8) Uani 1 1 d . U . . .
H15 H 0.643372 0.912214 0.689436 0.038 Uiso 1 1 calc R U . . .
C16 C 0.5398(5) 0.8216(4) 0.6044(2) 0.0276(8) Uani 1 1 d . U . . .
C17 C 0.3989(5) 0.7879(4) 0.6647(2) 0.0353(9) Uani 1 1 d . U . . .
H17 H 0.380575 0.813582 0.723546 0.042 Uiso 1 1 calc R U . . .
C18 C 0.2927(5) 0.7208(4) 0.6393(2) 0.0336(9) Uani 1 1 d . U . . .
H18 H 0.202742 0.696311 0.680651 0.040 Uiso 1 1 calc R U . . .
C19 C 0.3137(4) 0.6854(4) 0.5498(2) 0.0250(7) Uani 1 1 d . U . . .
C20 C 0.2060(4) 0.6120(4) 0.5216(2) 0.0292(8) Uani 1 1 d . U . . .
H20 H 0.117993 0.583026 0.562023 0.035 Uiso 1 1 calc R U . . .
C21 C 0.2289(4) 0.5829(4) 0.4361(2) 0.0308(8) Uani 1 1 d . U . . .
H21 H 0.159166 0.532059 0.416074 0.037 Uiso 1 1 calc R U . . .
C22 C 0.3573(4) 0.6297(4) 0.3788(2) 0.0282(8) Uani 1 1 d . U . . .
H22 H 0.368810 0.612659 0.319111 0.034 Uiso 1 1 calc R U . . .
C23 C 0.4459(4) 0.7211(3) 0.4879(2) 0.0206(7) Uani 1 1 d . U . . .
C24 C 0.5666(4) 0.7883(3) 0.5164(2) 0.0224(7) Uani 1 1 d . U . . .
N1 N 0.7035(4) 0.8118(3) 0.45813(17) 0.0233(6) Uani 1 1 d . U . . .
N2 N 0.4645(3) 0.6966(3) 0.40191(17) 0.0232(6) Uani 1 1 d . U . . .
O1 O 0.8944(3) 0.6196(2) 0.32761(14) 0.0265(6) Uani 1 1 d . U . . .
H1 H 0.822(4) 0.691(3) 0.3592(19) 0.040 Uiso 1 1 calc R U . . .
O2 O 0.5783(3) 0.8522(2) 0.25815(14) 0.0291(6) Uani 1 1 d . U . . .
H2 H 0.558(5) 0.796(3) 0.2980(19) 0.044 Uiso 1 1 calc R U . . .
Cl1 Cl 1.15709(13) 0.38556(9) 0.22251(6) 0.0369(3) Uani 1 1 d . U . . .
Cl2 Cl 1.08840(14) 1.05748(10) 0.18607(6) 0.0425(3) Uani 1 1 d . U . . .
Cl3 Cl 0.62907(15) 1.04582(10) 0.11016(6) 0.0446(3) Uani 1 1 d . U . . .
Cl4 Cl 0.77283(13) 0.36348(10) 0.09912(6) 0.0412(3) 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 122.8(3) . . ?
O1 C1 C2 118.5(3) . . ?
C6 C1 C2 118.6(3) . . ?
C3 C2 C1 121.4(3) . . ?
C3 C2 Cl1 119.9(3) . . ?
C1 C2 Cl1 118.8(3) . . ?
C4 C3 C2 120.3(3) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 118.4(3) . . ?
C3 C4 H4 120.8 . . ?
C5 C4 H4 120.8 . . ?
C4 C5 C6 122.6(3) . . ?
C4 C5 Cl2 120.1(3) . . ?
C6 C5 Cl2 117.3(3) . . ?
C5 C6 C1 118.6(3) . . ?
C5 C6 H6 120.7 . . ?
C1 C6 H6 120.7 . . ?
O2 C7 C12 123.7(3) . . ?
O2 C7 C8 118.5(3) . . ?
C12 C7 C8 117.8(3) . . ?
C9 C8 C7 121.0(3) . . ?
C9 C8 Cl3 120.1(3) . . ?
C7 C8 Cl3 118.9(3) . . ?
C8 C9 C10 120.7(3) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C11 C10 C9 118.2(3) . . ?
C11 C10 H10 120.9 . . ?
C9 C10 H10 120.9 . . ?
C12 C11 C10 121.9(3) . . ?
C12 C11 Cl4 118.9(3) . . ?
C10 C11 Cl4 119.1(3) . . ?
C11 C12 C7 120.4(3) . . ?
C11 C12 H12 119.8 . . ?
C7 C12 H12 119.8 . . ?
N1 C13 C14 123.6(3) . . ?
N1 C13 H13 118.2 . . ?
C14 C13 H13 118.2 . . ?
C15 C14 C13 119.2(3) . . ?
C15 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
C14 C15 C16 119.2(3) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 H15 120.4 . . ?
C24 C16 C15 117.7(3) . . ?
C24 C16 C17 120.6(3) . . ?
C15 C16 C17 121.7(3) . . ?
C18 C17 C16 120.9(3) . . ?
C18 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
C17 C18 C19 120.7(3) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
C23 C19 C20 117.9(3) . . ?
C23 C19 C18 120.3(3) . . ?
C20 C19 C18 121.8(3) . . ?
C21 C20 C19 119.6(3) . . ?
C21 C20 H20 120.2 . . ?
C19 C20 H20 120.2 . . ?
C20 C21 C22 118.3(3) . . ?
C20 C21 H21 120.8 . . ?
C22 C21 H21 120.8 . . ?
N2 C22 C21 124.6(3) . . ?
N2 C22 H22 117.7 . . ?
C21 C22 H22 117.7 . . ?
N2 C23 C19 122.3(3) . . ?
N2 C23 C24 118.9(3) . . ?
C19 C23 C24 118.9(3) . . ?
N1 C24 C16 122.4(3) . . ?
N1 C24 C23 119.1(3) . . ?
C16 C24 C23 118.5(3) . . ?
C13 N1 C24 117.9(3) . . ?
C22 N2 C23 117.2(3) . . ?
C1 O1 H1 109.5 . . ?
C7 O2 H2 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 1.356(3) . ?
C1 C6 1.393(4) . ?
C1 C2 1.394(4) . ?
C2 C3 1.379(4) . ?
C2 Cl1 1.747(3) . ?
C3 C4 1.375(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.376(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.390(4) . ?
C5 Cl2 1.748(3) . ?
C6 H6 0.9500 . ?
C7 O2 1.348(4) . ?
C7 C12 1.391(4) . ?
C7 C8 1.401(4) . ?
C8 C9 1.372(5) . ?
C8 Cl3 1.742(3) . ?
C9 C10 1.384(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.380(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.367(4) . ?
C11 Cl4 1.747(3) . ?
C12 H12 0.9500 . ?
C13 N1 1.331(4) . ?
C13 C14 1.393(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.362(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.414(5) . ?
C15 H15 0.9500 . ?
C16 C24 1.409(4) . ?
C16 C17 1.432(5) . ?
C17 C18 1.339(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.443(5) . ?
C18 H18 0.9500 . ?
C19 C23 1.404(4) . ?
C19 C20 1.411(4) . ?
C20 C21 1.364(5) . ?
C20 H20 0.9500 . ?
C21 C22 1.394(4) . ?
C21 H21 0.9500 . ?
C22 N2 1.328(4) . ?
C22 H22 0.9500 . ?
C23 N2 1.366(4) . ?
C23 C24 1.459(4) . ?
C24 N1 1.355(4) . ?
O1 H1 0.86(3) . ?
O2 H2 0.82(4) . ?
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 179.9(3) . . . . ?
C6 C1 C2 C3 -1.0(5) . . . . ?
O1 C1 C2 Cl1 -0.1(4) . . . . ?
C6 C1 C2 Cl1 179.0(2) . . . . ?
C1 C2 C3 C4 1.5(5) . . . . ?
Cl1 C2 C3 C4 -178.5(3) . . . . ?
C2 C3 C4 C5 -0.6(5) . . . . ?
C3 C4 C5 C6 -0.8(5) . . . . ?
C3 C4 C5 Cl2 178.6(3) . . . . ?
C4 C5 C6 C1 1.3(5) . . . . ?
Cl2 C5 C6 C1 -178.1(3) . . . . ?
O1 C1 C6 C5 178.7(3) . . . . ?
C2 C1 C6 C5 -0.4(5) . . . . ?
O2 C7 C8 C9 -180.0(3) . . . . ?
C12 C7 C8 C9 -0.8(5) . . . . ?
O2 C7 C8 Cl3 0.4(4) . . . . ?
C12 C7 C8 Cl3 179.5(2) . . . . ?
C7 C8 C9 C10 1.7(6) . . . . ?
Cl3 C8 C9 C10 -178.7(3) . . . . ?
C8 C9 C10 C11 -1.0(6) . . . . ?
C9 C10 C11 C12 -0.4(6) . . . . ?
C9 C10 C11 Cl4 178.9(3) . . . . ?
C10 C11 C12 C7 1.2(5) . . . . ?
Cl4 C11 C12 C7 -178.0(3) . . . . ?
O2 C7 C12 C11 178.5(3) . . . . ?
C8 C7 C12 C11 -0.6(5) . . . . ?
N1 C13 C14 C15 0.2(5) . . . . ?
C13 C14 C15 C16 -0.4(5) . . . . ?
C14 C15 C16 C24 -0.8(5) . . . . ?
C14 C15 C16 C17 178.3(3) . . . . ?
C24 C16 C17 C18 1.7(5) . . . . ?
C15 C16 C17 C18 -177.3(3) . . . . ?
C16 C17 C18 C19 -2.2(5) . . . . ?
C17 C18 C19 C23 -0.1(5) . . . . ?
C17 C18 C19 C20 178.7(3) . . . . ?
C23 C19 C20 C21 -2.2(5) . . . . ?
C18 C19 C20 C21 179.0(3) . . . . ?
C19 C20 C21 C22 -1.1(5) . . . . ?
C20 C21 C22 N2 2.6(5) . . . . ?
C20 C19 C23 N2 4.6(5) . . . . ?
C18 C19 C23 N2 -176.6(3) . . . . ?
C20 C19 C23 C24 -176.0(3) . . . . ?
C18 C19 C23 C24 2.8(5) . . . . ?
C15 C16 C24 N1 2.3(5) . . . . ?
C17 C16 C24 N1 -176.7(3) . . . . ?
C15 C16 C24 C23 -179.9(3) . . . . ?
C17 C16 C24 C23 1.0(5) . . . . ?
N2 C23 C24 N1 -6.0(4) . . . . ?
C19 C23 C24 N1 174.6(3) . . . . ?
N2 C23 C24 C16 176.2(3) . . . . ?
C19 C23 C24 C16 -3.2(4) . . . . ?
C14 C13 N1 C24 1.2(5) . . . . ?
C16 C24 N1 C13 -2.5(5) . . . . ?
C23 C24 N1 C13 179.8(3) . . . . ?
C21 C22 N2 C23 -0.3(5) . . . . ?
C19 C23 N2 C22 -3.3(5) . . . . ?
C24 C23 N2 C22 177.3(3) . . . . ?
