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#$Date: 2022-05-13 01:42:36 +0300 (Fri, 13 May 2022) $
#$Revision: 275382 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/49/7244920.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_7244920
loop_
_publ_author_name
'Bosch, Eric'
'Ferrence, Gregory M.'
'Powell, Conrad'
'Unruh, Daniel K.'
'Krueger, Herman R.'
'Groeneman, Ryan'
_publ_section_title
;
 Cooperative non-covalent interactions and synthetic feed as driving
 forces to structural diversity within organic co-crystals containing
 isosteric perhalobenzenes
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D2CE00360K
_journal_year                    2022
_chemical_formula_moiety         'C15 H13 N O2, 0.5 C6 Cl4 I2'
_chemical_formula_sum            'C18 H13 Cl2 I N O2'
_chemical_formula_weight         473.09
_chemical_name_systematic
'hemikis(1,2,4,5-tetrachloro-3,6-diiodobenzene) methyl 4-[(1E)-2-(pyridin-4-yl)ethenyl]benzoate'
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-03-04 deposited with the CCDC.	2022-05-09 downloaded from the CCDC.
;
_cell_angle_alpha                114.5720(10)
_cell_angle_beta                 92.194(2)
_cell_angle_gamma                107.358(2)
_cell_formula_units_Z            2
_cell_length_a                   8.2756(2)
_cell_length_b                   10.2186(3)
_cell_length_c                   11.8757(4)
_cell_measurement_reflns_used    9882
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.72
_cell_measurement_theta_min      2.34
_cell_volume                     856.35(5)
_computing_cell_refinement       'APEX4 & SAINT (Bruker, 2021)'
_computing_data_collection       'APEX4 (Bruker, 2021)'
_computing_data_reduction        SAINT
_computing_molecular_graphics
;
Mercury CSD (Macrae et al., 2020)
;
_computing_publication_material
;
;
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measurement_details
;
 A total of 3672 frames were collected.  
 The total exposure time was 5.10 hours.
;
_diffrn_measurement_device_type  'Bruker APEX-II CCD diffractometer'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0176
_diffrn_reflns_av_unetI/netI     0.0127
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            32790
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.927
_diffrn_reflns_theta_min         1.919
_exptl_absorpt_coefficient_mu    2.192
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_correction_T_min  0.6770
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Apex4 v2021.4.0 (Bruker, 2021)

Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.835
_exptl_crystal_description       block
_exptl_crystal_F_000             462
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.752
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         6056
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.110
_refine_ls_R_factor_all          0.0185
_refine_ls_R_factor_gt           0.0162
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0149P)²+0.5237P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0377
_refine_ls_wR_factor_ref         0.0388
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5711
_reflns_number_total             6056
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ce00360k2.cif
_cod_data_source_block           GMF21028
_cod_original_cell_volume        856.35(4)
_cod_database_code               7244920
_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   0.600
_shelx_estimated_absorpt_t_max   0.735
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
I1 I 0.64432(2) -0.01561(2) 0.31648(2) 0.01419(2) Uani 1 1 d . . . . .
C1 C 0.86076(14) -0.00168(13) 0.42542(10) 0.01212(18) Uani 1 1 d . . . . .
Cl2 Cl 0.81371(4) 0.23418(3) 0.62109(3) 0.01671(5) Uani 1 1 d . . . . .
C2 C 0.91645(14) 0.10495(13) 0.55268(10) 0.01222(18) Uani 1 1 d . . . . .
Cl3 Cl 1.11460(4) 0.23762(4) 0.78296(3) 0.02129(6) Uani 1 1 d . . . . .
C3 C 1.05319(14) 0.10548(13) 0.62584(10) 0.01272(18) Uani 1 1 d . . . . .
C7 C -0.19717(17) 0.07792(15) 0.03394(12) 0.0193(2) Uani 1 1 d . . . . .
H7 H -0.179214 0.012082 0.066922 0.023 Uiso 1 1 calc R U . . .
C8 C -0.30772(17) 0.01747(15) -0.08006(12) 0.0205(2) Uani 1 1 d . . . . .
H8 H -0.365114 -0.090427 -0.122777 0.025 Uiso 1 1 calc R U . . .
N9 N -0.33829(14) 0.10241(13) -0.13346(10) 0.0194(2) Uani 1 1 d . . . . .
C10 C -0.25659(17) 0.25419(15) -0.07067(12) 0.0196(2) Uani 1 1 d . . . . .
H10 H -0.275715 0.316646 -0.106992 0.023 Uiso 1 1 calc R U . . .
C11 C -0.14541(17) 0.32524(15) 0.04470(12) 0.0183(2) Uani 1 1 d . . . . .
H11 H -0.092040 0.433656 0.085927 0.022 Uiso 1 1 calc R U . . .
C12 C -0.11232(15) 0.23649(14) 0.09996(11) 0.0150(2) Uani 1 1 d . . . . .
C13 C 0.00415(16) 0.31008(14) 0.22193(11) 0.0164(2) Uani 1 1 d . . . . .
H13 H 0.032983 0.417561 0.270624 0.020 Uiso 1 1 calc R U . . .
C14 C 0.07298(15) 0.23627(14) 0.26967(11) 0.0158(2) Uani 1 1 d . . . . .
H14 H 0.043826 0.128905 0.220110 0.019 Uiso 1 1 calc R U . . .
C15 C 0.18902(14) 0.30649(13) 0.39136(11) 0.01357(19) Uani 1 1 d . . . . .
C16 C 0.28767(15) 0.22596(13) 0.41277(11) 0.0147(2) Uani 1 1 d . . . . .
H16 H 0.277888 0.127930 0.348640 0.018 Uiso 1 1 calc R U . . .
C17 C 0.39929(15) 0.28779(13) 0.52647(11) 0.01436(19) Uani 1 1 d . . . . .
H17 H 0.467798 0.233376 0.538910 0.017 Uiso 1 1 calc R U . . .
C18 C 0.41122(14) 0.42970(13) 0.62261(10) 0.01283(19) Uani 1 1 d . . . . .
C19 C 0.31346(15) 0.51126(14) 0.60263(11) 0.0158(2) Uani 1 1 d . . . . .
H19 H 0.321469 0.608135 0.667731 0.019 Uiso 1 1 calc R U . . .
C20 C 0.20476(15) 0.45060(14) 0.48763(11) 0.0164(2) Uani 1 1 d . . . . .
H20 H 0.140332 0.507349 0.474011 0.020 Uiso 1 1 calc R U . . .
C21 C 0.52854(15) 0.48838(13) 0.74381(11) 0.01379(19) Uani 1 1 d . . . . .
O22 O 0.51382(12) 0.61580(11) 0.83465(8) 0.01873(17) Uani 1 1 d . . . . .
C23 C 0.62288(17) 0.67399(15) 0.95467(11) 0.0197(2) Uani 1 1 d . . . . .
H23A H 0.599992 0.593426 0.982477 0.030 Uiso 1 1 calc R U . . .
H23B H 0.598852 0.762064 1.016874 0.030 Uiso 1 1 calc R U . . .
H23C H 0.743982 0.706040 0.946293 0.030 Uiso 1 1 calc R U . . .
O24 O 0.62696(13) 0.42890(11) 0.76134(9) 0.02117(18) 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'
I I -0.4742 1.8119 '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
C3 C1 C2 118.11(10) 2_756 . ?
C3 C1 I1 120.43(8) 2_756 . ?
C2 C1 I1 121.36(8) . . ?
C3 C2 C1 120.53(10) . . ?
C3 C2 Cl2 119.39(8) . . ?
C1 C2 Cl2 120.06(8) . . ?
C1 C3 C2 121.36(10) 2_756 . ?
C1 C3 Cl3 120.00(8) 2_756 . ?
C2 C3 Cl3 118.64(8) . . ?
C8 C7 C12 119.52(12) . . ?
C8 C7 H7 120.2 . . ?
C12 C7 H7 120.2 . . ?
N9 C8 C7 123.82(12) . . ?
N9 C8 H8 118.1 . . ?
C7 C8 H8 118.1 . . ?
C10 N9 C8 116.75(11) . . ?
N9 C10 C11 123.54(12) . . ?
N9 C10 H10 118.2 . . ?
C11 C10 H10 118.2 . . ?
C10 C11 C12 119.72(12) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C7 C12 C11 116.64(11) . . ?
C7 C12 C13 123.08(11) . . ?
C11 C12 C13 120.27(11) . . ?
C14 C13 C12 124.59(11) . . ?
C14 C13 H13 117.7 . . ?
C12 C13 H13 117.7 . . ?
C13 C14 C15 125.83(11) . . ?
C13 C14 H14 117.1 . . ?
C15 C14 H14 117.1 . . ?
C20 C15 C16 118.65(10) . . ?
C20 C15 C14 122.66(11) . . ?
C16 C15 C14 118.68(11) . . ?
C17 C16 C15 120.75(11) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C16 C17 C18 120.15(11) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C17 C18 C19 119.70(10) . . ?
C17 C18 C21 117.97(10) . . ?
C19 C18 C21 122.33(10) . . ?
C20 C19 C18 119.99(11) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C19 C20 C15 120.72(11) . . ?
C19 C20 H20 119.6 . . ?
C15 C20 H20 119.6 . . ?
O24 C21 O22 122.61(11) . . ?
O24 C21 C18 124.45(11) . . ?
O22 C21 C18 112.94(10) . . ?
C21 O22 C23 114.49(10) . . ?
O22 C23 H23A 109.5 . . ?
O22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 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
I1 C1 2.1023(11) . ?
C1 C3 1.3964(15) 2_756 ?
C1 C2 1.4004(15) . ?
Cl2 C2 1.7197(11) . ?
C2 C3 1.3973(15) . ?
Cl3 C3 1.7280(11) . ?
C7 C8 1.3870(17) . ?
C7 C12 1.3985(17) . ?
C7 H7 0.9500 . ?
C8 N9 1.3402(17) . ?
C8 H8 0.9500 . ?
N9 C10 1.3388(17) . ?
C10 C11 1.3886(17) . ?
C10 H10 0.9500 . ?
C11 C12 1.3991(17) . ?
C11 H11 0.9500 . ?
C12 C13 1.4654(16) . ?
C13 C14 1.3424(17) . ?
C13 H13 0.9500 . ?
C14 C15 1.4648(16) . ?
C14 H14 0.9500 . ?
C15 C20 1.4024(16) . ?
C15 C16 1.4025(16) . ?
C16 C17 1.3865(16) . ?
C16 H16 0.9500 . ?
C17 C18 1.3947(16) . ?
C17 H17 0.9500 . ?
C18 C19 1.3991(16) . ?
C18 C21 1.4839(16) . ?
C19 C20 1.3884(16) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 O24 1.2098(14) . ?
C21 O22 1.3455(14) . ?
O22 C23 1.4410(15) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
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
C3 C1 C2 C3 -0.66(19) 2_756 . . . ?
I1 C1 C2 C3 175.55(9) . . . . ?
C3 C1 C2 Cl2 -179.34(9) 2_756 . . . ?
I1 C1 C2 Cl2 -3.13(13) . . . . ?
C1 C2 C3 C1 0.68(19) . . . 2_756 ?
Cl2 C2 C3 C1 179.37(9) . . . 2_756 ?
C1 C2 C3 Cl3 -179.03(9) . . . . ?
Cl2 C2 C3 Cl3 -0.35(14) . . . . ?
C12 C7 C8 N9 0.8(2) . . . . ?
C7 C8 N9 C10 -0.5(2) . . . . ?
C8 N9 C10 C11 -0.4(2) . . . . ?
N9 C10 C11 C12 1.0(2) . . . . ?
C8 C7 C12 C11 -0.20(19) . . . . ?
C8 C7 C12 C13 178.90(12) . . . . ?
C10 C11 C12 C7 -0.61(18) . . . . ?
C10 C11 C12 C13 -179.74(12) . . . . ?
C7 C12 C13 C14 16.0(2) . . . . ?
C11 C12 C13 C14 -164.98(12) . . . . ?
C12 C13 C14 C15 -179.71(11) . . . . ?
C13 C14 C15 C20 18.22(19) . . . . ?
C13 C14 C15 C16 -162.16(12) . . . . ?
C20 C15 C16 C17 -0.37(17) . . . . ?
C14 C15 C16 C17 179.99(11) . . . . ?
C15 C16 C17 C18 1.78(18) . . . . ?
C16 C17 C18 C19 -1.70(18) . . . . ?
C16 C17 C18 C21 178.10(11) . . . . ?
C17 C18 C19 C20 0.22(18) . . . . ?
C21 C18 C19 C20 -179.57(11) . . . . ?
C18 C19 C20 C15 1.19(19) . . . . ?
C16 C15 C20 C19 -1.12(18) . . . . ?
C14 C15 C20 C19 178.50(11) . . . . ?
C17 C18 C21 O24 7.37(18) . . . . ?
C19 C18 C21 O24 -172.83(12) . . . . ?
C17 C18 C21 O22 -172.05(10) . . . . ?
C19 C18 C21 O22 7.74(16) . . . . ?
O24 C21 O22 C23 -0.88(17) . . . . ?
C18 C21 O22 C23 178.56(10) . . . . ?
