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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/7/24/49/7244918.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_7244918
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, C6 F4 I2'
_chemical_formula_sum            'C21 H13 F4 I2 N O2'
_chemical_formula_weight         641.12
_chemical_name_systematic
'(1,2,4,5-tetrafluoro-3,6-diiodobenzene) methyl 4-[(1E)-2-(pyridin-4-yl)ethenyl]benzoate'
_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
_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                90
_cell_angle_beta                 93.249(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.3940(10)
_cell_length_b                   6.4768(4)
_cell_length_c                   38.606(2)
_cell_measurement_reflns_used    9985
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.38
_cell_measurement_theta_min      2.49
_cell_volume                     4092.6(4)
_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 0.999
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_details
;
 A total of 3672 frames were collected.  
 The total exposure time was 4.08 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  0.0574
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       52
_diffrn_reflns_limit_l_min       -53
_diffrn_reflns_number            51577
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.447
_diffrn_reflns_theta_min         2.489
_exptl_absorpt_coefficient_mu    3.128
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.6929
_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            colourless
_exptl_crystal_density_diffrn    2.081
_exptl_crystal_description       'plate - fragment'
_exptl_crystal_F_000             2432
_exptl_crystal_size_max          0.154
_exptl_crystal_size_mid          0.102
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.502
_refine_diff_density_min         -0.682
_refine_diff_density_rms         0.119
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         5403
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0261
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0159P)²+6.4456P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0447
_refine_ls_wR_factor_ref         0.0477
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4397
_reflns_number_total             5403
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ce00360k2.cif
_cod_data_source_block           GMF21034
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7244918
_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   0.644
_shelx_estimated_absorpt_t_max   0.811
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 0.70476(15) 0.9485(4) 0.41868(6) 0.0147(5) Uani 1 1 d . . . . .
I1 I 0.66878(2) 0.74959(3) 0.45822(2) 0.01642(5) Uani 1 1 d . . . . .
C2 C 0.66634(16) 1.1353(4) 0.41208(6) 0.0146(5) Uani 1 1 d . . . . .
F2 F 0.60312(10) 1.1927(2) 0.43091(4) 0.0225(4) Uani 1 1 d . . . . .
C3 C 0.68945(16) 1.2650(4) 0.38621(7) 0.0155(5) Uani 1 1 d . . . . .
F3 F 0.64826(9) 1.4432(2) 0.38106(4) 0.0211(3) Uani 1 1 d . . . . .
C4 C 0.75330(16) 1.2161(4) 0.36570(6) 0.0136(5) Uani 1 1 d . . . . .
I4 I 0.78610(2) 1.41233(3) 0.32601(2) 0.01585(5) Uani 1 1 d . . . . .
C5 C 0.79208(16) 1.0296(4) 0.37234(7) 0.0157(6) Uani 1 1 d . . . . .
F5 F 0.85529(9) 0.9717(2) 0.35349(4) 0.0212(4) Uani 1 1 d . . . . .
C6 C 0.76854(16) 0.9000(4) 0.39809(6) 0.0146(5) Uani 1 1 d . . . . .
F6 F 0.80945(10) 0.7202(2) 0.40315(4) 0.0207(3) Uani 1 1 d . . . . .
C7 C 0.54304(17) 0.4693(4) 0.56250(7) 0.0191(6) Uani 1 1 d . . . . .
H7 H 0.507874 0.534181 0.577920 0.023 Uiso 1 1 calc R U . . .
C8 C 0.56870(17) 0.5746(5) 0.53401(7) 0.0207(6) Uani 1 1 d . . . . .
H8 H 0.550245 0.712467 0.530504 0.025 Uiso 1 1 calc R U . . .
N9 N 0.61796(14) 0.4945(4) 0.51104(6) 0.0208(5) Uani 1 1 d . . . . .
C10 C 0.64288(17) 0.3011(4) 0.51662(7) 0.0212(6) Uani 1 1 d . . . . .
H10 H 0.677782 0.240748 0.500609 0.025 Uiso 1 1 calc R U . . .
C11 C 0.62070(17) 0.1832(4) 0.54449(7) 0.0197(6) Uani 1 1 d . . . . .
H11 H 0.640493 0.046004 0.547289 0.024 Uiso 1 1 calc R U . . .
C12 C 0.56916(15) 0.2665(4) 0.56847(7) 0.0158(5) Uani 1 1 d . . . . .
C13 C 0.54393(16) 0.1427(4) 0.59774(7) 0.0168(6) Uani 1 1 d . . . . .
H13 H 0.564267 0.005622 0.599663 0.020 Uiso 1 1 calc R U . . .
C14 C 0.49476(16) 0.2067(4) 0.62190(7) 0.0188(6) Uani 1 1 d . . . . .
H14 H 0.475619 0.344783 0.619781 0.023 Uiso 1 1 calc R U . . .
C15 C 0.46684(16) 0.0888(4) 0.65132(7) 0.0173(5) Uani 1 1 d . . . . .
C16 C 0.41025(17) 0.1800(4) 0.67245(7) 0.0206(6) Uani 1 1 d . . . . .
H16 H 0.391196 0.315782 0.667326 0.025 Uiso 1 1 calc R U . . .
C17 C 0.38145(17) 0.0761(4) 0.70073(7) 0.0213(6) Uani 1 1 d . . . . .
H17 H 0.343460 0.141110 0.714883 0.026 Uiso 1 1 calc R U . . .
C18 C 0.40821(16) -0.1228(4) 0.70828(7) 0.0172(6) Uani 1 1 d . . . . .
C19 C 0.46395(17) -0.2162(4) 0.68711(7) 0.0182(6) Uani 1 1 d . . . . .
H19 H 0.482273 -0.352777 0.692072 0.022 Uiso 1 1 calc R U . . .
C20 C 0.49255(16) -0.1124(4) 0.65917(7) 0.0188(6) Uani 1 1 d . . . . .
H20 H 0.530299 -0.178409 0.645014 0.023 Uiso 1 1 calc R U . . .
C21 C 0.37612(16) -0.2289(5) 0.73897(7) 0.0194(6) Uani 1 1 d . . . . .
O22 O 0.40244(12) -0.4250(3) 0.74108(5) 0.0219(4) Uani 1 1 d . . . . .
C23 C 0.37200(19) -0.5442(5) 0.76919(7) 0.0260(7) Uani 1 1 d . . . . .
H23A H 0.402699 -0.673736 0.771658 0.039 Uiso 1 1 calc R U . . .
H23B H 0.313983 -0.574840 0.764198 0.039 Uiso 1 1 calc R U . . .
H23C H 0.378667 -0.465037 0.790794 0.039 Uiso 1 1 calc R U . . .
O24 O 0.33216(13) -0.1515(3) 0.75923(5) 0.0259(5) 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'
F F 0.0171 0.0103 '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
C2 C1 C6 116.4(2) . . ?
C2 C1 I1 121.73(19) . . ?
C6 C1 I1 121.90(19) . . ?
F2 C2 C3 118.3(2) . . ?
F2 C2 C1 119.8(2) . . ?
C3 C2 C1 121.9(2) . . ?
F3 C3 C2 118.4(2) . . ?
F3 C3 C4 120.0(2) . . ?
C2 C3 C4 121.6(2) . . ?
C5 C4 C3 116.6(2) . . ?
C5 C4 I4 122.28(19) . . ?
C3 C4 I4 121.07(18) . . ?
F5 C5 C6 118.4(2) . . ?
F5 C5 C4 120.1(2) . . ?
C6 C5 C4 121.6(2) . . ?
F6 C6 C5 118.3(2) . . ?
F6 C6 C1 119.8(2) . . ?
C5 C6 C1 121.9(2) . . ?
C8 C7 C12 119.5(3) . . ?
C8 C7 H7 120.3 . . ?
C12 C7 H7 120.3 . . ?
N9 C8 C7 124.0(3) . . ?
N9 C8 H8 118.0 . . ?
C7 C8 H8 118.0 . . ?
C10 N9 C8 116.7(2) . . ?
N9 C10 C11 123.6(3) . . ?
N9 C10 H10 118.2 . . ?
C11 C10 H10 118.2 . . ?
C10 C11 C12 119.8(3) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C7 C12 C11 116.4(2) . . ?
C7 C12 C13 123.0(2) . . ?
C11 C12 C13 120.5(2) . . ?
C14 C13 C12 125.4(2) . . ?
C14 C13 H13 117.3 . . ?
C12 C13 H13 117.3 . . ?
C13 C14 C15 127.5(3) . . ?
C13 C14 H14 116.2 . . ?
C15 C14 H14 116.2 . . ?
C20 C15 C16 118.0(2) . . ?
C20 C15 C14 123.4(2) . . ?
C16 C15 C14 118.6(2) . . ?
C17 C16 C15 121.3(3) . . ?
C17 C16 H16 119.3 . . ?
C15 C16 H16 119.3 . . ?
C18 C17 C16 119.9(3) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C18 C19 119.3(2) . . ?
C17 C18 C21 118.3(2) . . ?
C19 C18 C21 122.5(2) . . ?
C20 C19 C18 120.7(2) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C19 C20 C15 120.9(3) . . ?
C19 C20 H20 119.5 . . ?
C15 C20 H20 119.5 . . ?
O24 C21 O22 123.9(2) . . ?
O24 C21 C18 125.1(3) . . ?
O22 C21 C18 111.0(2) . . ?
C21 O22 C23 115.3(2) . . ?
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
C1 C2 1.381(4) . ?
C1 C6 1.385(4) . ?
C1 I1 2.107(2) . ?
C2 F2 1.351(3) . ?
C2 C3 1.374(4) . ?
C3 F3 1.346(3) . ?
C3 C4 1.385(4) . ?
C4 C5 1.382(4) . ?
C4 I4 2.084(2) . ?
C5 F5 1.353(3) . ?
C5 C6 1.373(4) . ?
C6 F6 1.352(3) . ?
C7 C8 1.380(4) . ?
C7 C12 1.397(4) . ?
C7 H7 0.9500 . ?
C8 N9 1.338(4) . ?
C8 H8 0.9500 . ?
N9 C10 1.331(4) . ?
C10 C11 1.385(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.397(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.464(4) . ?
C13 C14 1.333(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.463(4) . ?
C14 H14 0.9500 . ?
C15 C20 1.398(4) . ?
C15 C16 1.400(4) . ?
C16 C17 1.388(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.387(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.398(4) . ?
C18 C21 1.491(4) . ?
C19 C20 1.376(4) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 O24 1.203(3) . ?
C21 O22 1.342(3) . ?
O22 C23 1.444(3) . ?
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
C6 C1 C2 F2 179.4(2) . . . . ?
I1 C1 C2 F2 -1.0(3) . . . . ?
C6 C1 C2 C3 0.8(4) . . . . ?
I1 C1 C2 C3 -179.7(2) . . . . ?
F2 C2 C3 F3 0.4(4) . . . . ?
C1 C2 C3 F3 179.1(2) . . . . ?
F2 C2 C3 C4 -179.6(2) . . . . ?
C1 C2 C3 C4 -0.9(4) . . . . ?
F3 C3 C4 C5 -179.4(2) . . . . ?
C2 C3 C4 C5 0.6(4) . . . . ?
F3 C3 C4 I4 -1.1(3) . . . . ?
C2 C3 C4 I4 178.9(2) . . . . ?
C3 C4 C5 F5 -179.6(2) . . . . ?
I4 C4 C5 F5 2.1(3) . . . . ?
C3 C4 C5 C6 -0.2(4) . . . . ?
I4 C4 C5 C6 -178.5(2) . . . . ?
F5 C5 C6 F6 -0.4(4) . . . . ?
C4 C5 C6 F6 -179.8(2) . . . . ?
F5 C5 C6 C1 179.6(2) . . . . ?
C4 C5 C6 C1 0.2(4) . . . . ?
C2 C1 C6 F6 179.6(2) . . . . ?
I1 C1 C6 F6 0.1(3) . . . . ?
C2 C1 C6 C5 -0.4(4) . . . . ?
I1 C1 C6 C5 -179.94(19) . . . . ?
C12 C7 C8 N9 0.1(4) . . . . ?
C7 C8 N9 C10 0.0(4) . . . . ?
C8 N9 C10 C11 -0.2(4) . . . . ?
N9 C10 C11 C12 0.3(4) . . . . ?
C8 C7 C12 C11 0.0(4) . . . . ?
C8 C7 C12 C13 -179.1(3) . . . . ?
C10 C11 C12 C7 -0.2(4) . . . . ?
C10 C11 C12 C13 178.9(3) . . . . ?
C7 C12 C13 C14 -0.6(4) . . . . ?
C11 C12 C13 C14 -179.6(3) . . . . ?
C12 C13 C14 C15 179.1(3) . . . . ?
C13 C14 C15 C20 3.4(5) . . . . ?
C13 C14 C15 C16 -175.4(3) . . . . ?
C20 C15 C16 C17 1.1(4) . . . . ?
C14 C15 C16 C17 180.0(3) . . . . ?
C15 C16 C17 C18 -0.6(4) . . . . ?
C16 C17 C18 C19 -0.2(4) . . . . ?
C16 C17 C18 C21 179.7(3) . . . . ?
C17 C18 C19 C20 0.4(4) . . . . ?
C21 C18 C19 C20 -179.5(3) . . . . ?
C18 C19 C20 C15 0.2(4) . . . . ?
C16 C15 C20 C19 -0.9(4) . . . . ?
C14 C15 C20 C19 -179.7(3) . . . . ?
C17 C18 C21 O24 -4.7(4) . . . . ?
C19 C18 C21 O24 175.2(3) . . . . ?
C17 C18 C21 O22 174.9(2) . . . . ?
C19 C18 C21 O22 -5.2(4) . . . . ?
O24 C21 O22 C23 2.1(4) . . . . ?
C18 C21 O22 C23 -177.6(2) . . . . ?
