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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/7/24/74/7247446.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_7247446
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            'C16 H12 Cl2 N2 O'
_chemical_formula_weight         319.18
_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                 99.747(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.5285(11)
_cell_length_b                   7.0970(7)
_cell_length_c                   19.468(2)
_cell_measurement_reflns_used    11915
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.6
_cell_measurement_theta_min      3.1
_cell_volume                     1433.7(3)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_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  0.0492
_diffrn_reflns_av_unetI/netI     0.0355
_diffrn_reflns_Laue_measured_fraction_full 0.999
_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       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            14484
_diffrn_reflns_point_group_measured_fraction_full 0.999
_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         3.060
_exptl_absorpt_coefficient_mu    0.452
_exptl_crystal_density_diffrn    1.479
_exptl_crystal_description       Plate
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.370
_refine_diff_density_min         -0.438
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3277
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0646
_refine_ls_R_factor_gt           0.0451
_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)+(0.0300P)²+0.8439P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0904
_refine_ls_wR_factor_ref         0.0970
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2492
_reflns_number_total             3277
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ce00672g1.cif
_cod_data_source_block           datam_CCDC4
_cod_depositor_comments
'Adding full bibliography for 7247442--7247454.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7247446
_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   0.895
_shelx_estimated_absorpt_t_max   0.948
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 0.1737(2) 0.6319(3) 0.54489(11) 0.0309(5) Uani 1 1 d . . . . .
C2 C 0.11347(19) 0.5814(3) 0.60117(11) 0.0289(5) Uani 1 1 d . . . . .
C3 C 0.08882(19) 0.3935(3) 0.61278(11) 0.0308(5) Uani 1 1 d . . . . .
C4 C 0.1189(2) 0.2538(3) 0.56890(12) 0.0350(5) Uani 1 1 d . . . . .
H4 H 0.100494 0.125488 0.577006 0.042 Uiso 1 1 calc R U . . .
C5 C 0.1764(2) 0.3049(3) 0.51288(12) 0.0372(5) Uani 1 1 d . . . . .
H5 H 0.197092 0.210339 0.482054 0.045 Uiso 1 1 calc R U . . .
C6 C 0.2042(2) 0.4906(3) 0.50094(11) 0.0357(5) Uani 1 1 d . . . . .
H6 H 0.244437 0.522276 0.462365 0.043 Uiso 1 1 calc R U . . .
C7 C 0.2743(2) 0.9236(3) 0.37083(13) 0.0394(6) Uani 1 1 d . . . . .
H7 H 0.186478 0.958311 0.368075 0.047 Uiso 1 1 calc R U . . .
C8 C 0.3265(2) 0.9282(3) 0.31027(11) 0.0326(5) Uani 1 1 d . . . . .
H8 H 0.274934 0.963246 0.267312 0.039 Uiso 1 1 calc R U . . .
C9 C 0.4555(2) 0.8810(3) 0.31301(10) 0.0267(4) Uani 1 1 d . . . . .
C10 C 0.5246(2) 0.8311(3) 0.37760(11) 0.0339(5) Uani 1 1 d . . . . .
H10 H 0.613133 0.798602 0.382284 0.041 Uiso 1 1 calc R U . . .
C11 C 0.4633(3) 0.8292(3) 0.43515(12) 0.0423(6) Uani 1 1 d . . . . .
H11 H 0.512155 0.794360 0.478885 0.051 Uiso 1 1 calc R U . . .
C12 C 0.6992(3) 0.9137(3) 0.19232(14) 0.0459(6) Uani 1 1 d . . . . .
H12 H 0.789046 0.935695 0.195849 0.055 Uiso 1 1 calc R U . . .
C13 C 0.6478(2) 0.9138(3) 0.25337(12) 0.0361(5) Uani 1 1 d . . . . .
H13 H 0.701505 0.935355 0.297000 0.043 Uiso 1 1 calc R U . . .
C14 C 0.5167(2) 0.8820(3) 0.24988(11) 0.0283(5) Uani 1 1 d . . . . .
C15 C 0.4449(2) 0.8509(3) 0.18414(10) 0.0343(5) Uani 1 1 d . . . . .
H15 H 0.354884 0.827773 0.178817 0.041 Uiso 1 1 calc R U . . .
C16 C 0.5057(3) 0.8542(3) 0.12667(12) 0.0470(7) Uani 1 1 d . . . . .
H16 H 0.454541 0.833075 0.082251 0.056 Uiso 1 1 calc R U . . .
N1 N 0.3395(2) 0.8735(3) 0.43261(10) 0.0411(5) Uani 1 1 d . . . . .
N2 N 0.6312(2) 0.8848(3) 0.12925(11) 0.0496(6) Uani 1 1 d . . . . .
O1 O 0.20076(17) 0.8161(2) 0.53703(9) 0.0417(4) Uani 1 1 d . . . . .
H1 H 0.240(3) 0.8285(7) 0.5037(14) 0.063 Uiso 1 1 calc R U . . .
Cl1 Cl 0.07155(6) 0.75813(8) 0.65458(3) 0.03951(16) Uani 1 1 d . . . . .
Cl2 Cl 0.02118(6) 0.32961(9) 0.68512(3) 0.04803(19) 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 123.57(18) . . ?
O1 C1 C2 117.86(18) . . ?
C6 C1 C2 118.56(19) . . ?
C3 C2 C1 119.73(18) . . ?
C3 C2 Cl1 121.69(16) . . ?
C1 C2 Cl1 118.58(16) . . ?
C4 C3 C2 121.45(19) . . ?
C4 C3 Cl2 118.80(17) . . ?
C2 C3 Cl2 119.74(16) . . ?
C3 C4 C5 118.5(2) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 H4 120.7 . . ?
C6 C5 C4 121.2(2) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C1 120.6(2) . . ?
C5 C6 H6 119.7 . . ?
C1 C6 H6 119.7 . . ?
N1 C7 C8 124.0(2) . . ?
N1 C7 H7 118.0 . . ?
C8 C7 H7 118.0 . . ?
C7 C8 C9 119.2(2) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 H8 120.4 . . ?
C10 C9 C8 117.05(19) . . ?
C10 C9 C14 121.2(2) . . ?
C8 C9 C14 121.77(19) . . ?
C11 C10 C9 119.4(2) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
N1 C11 C10 123.6(2) . . ?
N1 C11 H11 118.2 . . ?
C10 C11 H11 118.2 . . ?
N2 C12 C13 124.4(2) . . ?
N2 C12 H12 117.8 . . ?
C13 C12 H12 117.8 . . ?
C12 C13 C14 119.1(2) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
C13 C14 C15 116.90(19) . . ?
C13 C14 C9 121.9(2) . . ?
C15 C14 C9 121.2(2) . . ?
C16 C15 C14 119.3(2) . . ?
C16 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
N2 C16 C15 124.4(2) . . ?
N2 C16 H16 117.8 . . ?
C15 C16 H16 117.8 . . ?
C7 N1 C11 116.64(19) . . ?
C12 N2 C16 115.9(2) . . ?
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 1.352(2) . ?
C1 C6 1.391(3) . ?
C1 C2 1.403(3) . ?
C2 C3 1.385(3) . ?
C2 Cl1 1.733(2) . ?
C3 C4 1.380(3) . ?
C3 Cl2 1.742(2) . ?
C4 C5 1.382(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.378(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 N1 1.328(3) . ?
C7 C8 1.383(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.390(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.388(3) . ?
C9 C14 1.482(3) . ?
C10 C11 1.384(3) . ?
C10 H10 0.9500 . ?
C11 N1 1.334(3) . ?
C11 H11 0.9500 . ?
C12 N2 1.329(3) . ?
C12 C13 1.387(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.388(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.390(3) . ?
C15 C16 1.380(3) . ?
C15 H15 0.9500 . ?
C16 N2 1.331(3) . ?
C16 H16 0.9500 . ?
O1 H1 0.83(3) . ?
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 -177.4(2) . . . . ?
C6 C1 C2 C3 1.7(3) . . . . ?
O1 C1 C2 Cl1 2.7(3) . . . . ?
C6 C1 C2 Cl1 -178.26(17) . . . . ?
C1 C2 C3 C4 -1.9(3) . . . . ?
Cl1 C2 C3 C4 178.03(17) . . . . ?
C1 C2 C3 Cl2 176.86(16) . . . . ?
Cl1 C2 C3 Cl2 -3.2(3) . . . . ?
C2 C3 C4 C5 0.8(3) . . . . ?
Cl2 C3 C4 C5 -177.93(17) . . . . ?
C3 C4 C5 C6 0.4(3) . . . . ?
C4 C5 C6 C1 -0.6(4) . . . . ?
O1 C1 C6 C5 178.5(2) . . . . ?
C2 C1 C6 C5 -0.4(3) . . . . ?
N1 C7 C8 C9 -1.0(3) . . . . ?
C7 C8 C9 C10 0.1(3) . . . . ?
C7 C8 C9 C14 179.55(19) . . . . ?
C8 C9 C10 C11 0.5(3) . . . . ?
C14 C9 C10 C11 -179.0(2) . . . . ?
C9 C10 C11 N1 -0.2(4) . . . . ?
N2 C12 C13 C14 0.0(4) . . . . ?
C12 C13 C14 C15 0.2(3) . . . . ?
C12 C13 C14 C9 -179.7(2) . . . . ?
C10 C9 C14 C13 -28.1(3) . . . . ?
C8 C9 C14 C13 152.5(2) . . . . ?
C10 C9 C14 C15 152.0(2) . . . . ?
C8 C9 C14 C15 -27.5(3) . . . . ?
C13 C14 C15 C16 -0.3(3) . . . . ?
C9 C14 C15 C16 179.6(2) . . . . ?
C14 C15 C16 N2 0.2(4) . . . . ?
C8 C7 N1 C11 1.3(3) . . . . ?
C10 C11 N1 C7 -0.7(3) . . . . ?
C13 C12 N2 C16 -0.1(4) . . . . ?
C15 C16 N2 C12 0.0(4) . . . . ?
