# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_GMF21034
_database_code_depnum_ccdc_archive 'CCDC 2156801'
loop_
_audit_author_name
_audit_author_address
'Gregory Ferrence'
;Illinois State University
United States of America
;
_audit_update_record             
;
2022-03-04 deposited with the CCDC.	2022-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
'(1,2,4,5-tetrafluoro-3,6-diiodobenzene) methyl 4-[(1E)-2-(pyridin-4-yl)ethenyl]benzoate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H13 N O2, C6 F4 I2'
_chemical_formula_sum            'C21 H13 F4 I2 N O2'
_chemical_formula_weight         641.12

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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.
;

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'

_cell_length_a                   16.3940(10)
_cell_length_b                   6.4768(4)
_cell_length_c                   38.606(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.249(3)
_cell_angle_gamma                90
_cell_volume                     4092.6(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9985
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      27.38

_exptl_crystal_description       'plate - fragment'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.081
_exptl_crystal_F_000             2432
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.154
_exptl_crystal_size_mid          0.102
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    3.128
_shelx_estimated_absorpt_T_min   0.644
_shelx_estimated_absorpt_T_max   0.811
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6929
_exptl_absorpt_correction_T_max  0.7459
_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_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD diffractometer'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_measurement_details      
;
 A total of 3672 frames were collected.  
 The total exposure time was 4.08 hours.
;
_diffrn_reflns_number            51577
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_av_R_equivalents  0.0574
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -53
_diffrn_reflns_limit_l_max       52
_diffrn_reflns_theta_min         2.489
_diffrn_reflns_theta_max         29.447
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5403
_reflns_number_gt                4397
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX4 (Bruker, 2021)'
_computing_cell_refinement       'APEX4 & SAINT (Bruker, 2021)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015b)'
_computing_molecular_graphics    
;
Mercury CSD (Macrae et al., 2020)
;
_computing_publication_material  
;
;

_refine_special_details          
;
All non-H atoms were refined anisotropically.  All H 
atoms were identifiable in the difference Fourier, but 
were included in the final refinement using 
the riding-model approximation.
d(C--H) = 
0.95 Å Uiso = 1.2Ueq (C) for aromatic, 
and
0.98 Å , Uiso = 1.5Ueq (C) for methyl 
H atoms. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0159P)²+6.4456P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5403
_refine_ls_number_parameters     272
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0261
_refine_ls_wR_factor_ref         0.0477
_refine_ls_wR_factor_gt          0.0447
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

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 . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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_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_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) . . . . ?

_refine_diff_density_max         0.502
_refine_diff_density_min         -0.682
_refine_diff_density_rms         0.119

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_C6I2F4_2_4-PEBE
_database_code_depnum_ccdc_archive 'CCDC 2168646'
loop_
_audit_author_name
_audit_author_address
'Daniel Unruh'
;Texas Tech University
United States of America
;
_audit_update_record             
;
2022-04-25 deposited with the CCDC.	2022-05-09 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT088_C6I2F4_2_4-PEBE     
;
PROBLEM: Poor Data / Parameter Ratio ....................       8.64 Note  
RESPONSE: Due to the significant number of disordered atom sites in this
          structure.
;
_vrf_PLAT911_C6I2F4_2_4-PEBE     
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600         13 Report
RESPONSE: These reflections were omitted during the absorption correction.
;
# end Validation Reply Form

_audit_creation_date             2022-04-15
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.11.18 svn.ra9532c28 for OlexSys, GUI svn.r6429)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
' ryangroeneman19@webster.edu'
daniel.unruh@ttu.edu
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C36 H26 F4 I2 N2 O4'
_chemical_formula_sum            'C36 H26 F4 I2 N2 O4'
_chemical_formula_weight         880.39
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C40  H22  F4  I2  N2  O4  '
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.26700(10)
_cell_length_b                   11.0627(2)
_cell_length_c                   12.1817(3)
_cell_angle_alpha                76.276(2)
_cell_angle_beta                 83.834(2)
_cell_angle_gamma                83.200(2)
_cell_volume                     811.91(3)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    12277
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.9430
_cell_measurement_theta_min      3.7220
_shelx_estimated_absorpt_T_max   0.649
_shelx_estimated_absorpt_T_min   0.152
_exptl_absorpt_coefficient_mu    15.791
_exptl_absorpt_correction_T_max  0.902
_exptl_absorpt_correction_T_min  0.191
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.51a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.801
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             430
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 0 0.0131
0 1 0 0.0169
4 2 3 0.0837
-4 -2 -3 0.0854
-1 1 7 0.0655
-3 2 3 0.0463
1 -1 -7 0.0601
4 -2 -2 0.0648
2 -1 7 0.0894
-3 1 -6 0.0845
3 -2 -5 0.0638
4 -2 0 0.0633
1 4 -6 0.0455
3 2 -3 0.0619
1 6 5 0.0505

_exptl_crystal_size_max          0.191
_exptl_crystal_size_mid          0.118
_exptl_crystal_size_min          0.03
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0001 -0.9993 -0.0001 -0.0033 0.1303 0.0610
-0.0001 0.9993 0.0001 0.0033 -0.1303 -0.0610
3.8900 1.7368 3.0521 0.0371 -0.4820 0.8754
-3.8932 -1.6624 -3.0503 -0.0364 0.4726 -0.8805
-1.0808 0.9392 7.3401 0.9967 0.0789 0.0199
-3.2938 1.9649 3.4518 0.7188 0.0562 -0.6929
0.8465 -0.8179 -7.4841 -0.9933 -0.0787 -0.0847
3.6133 -2.0589 -1.7515 -0.5391 -0.0419 0.8412
2.1007 -0.8390 6.5288 0.6116 0.0491 0.7896
-2.5890 1.1435 -5.7393 -0.4710 -0.0381 -0.8813
2.8324 -1.7729 -4.8749 -0.8518 -0.0679 0.5195
3.7384 -2.0301 0.0237 -0.3327 -0.0272 0.9426
0.6371 3.6659 -5.5221 -0.7199 -0.6158 -0.3202
3.3783 1.9419 -3.0378 -0.6626 -0.5658 0.4907
0.7819 6.4611 5.0173 0.5667 -0.8238 -0.0088

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0664
_diffrn_reflns_av_unetI/netI     0.0440
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15382
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.114
_diffrn_reflns_theta_min         3.748
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -41.00  25.00   0.50    0.05    --  -47.76  38.00 150.00  132
  2  ω    -25.00  28.00   0.50    0.05    --  -47.76  19.00 -60.00  106
  3  ω    -25.00  28.00   0.50    0.05    --  -47.76  19.00-120.00  106
  4  ω    -25.00  28.00   0.50    0.05    --  -47.76  19.00-150.00  106
  5  ω     25.00 121.00   0.50    0.05    --   47.76  77.00 -60.00  192
  6  ω     25.00 121.00   0.50    0.05    --   47.76  77.00 120.00  192
  7  ω     25.00 121.00   0.50    0.05    --   47.76  77.00  90.00  192
  8  ω     33.00 120.00   0.50    0.05    --   47.76  57.00  30.00  174
  9  ω     25.00 121.00   0.50    0.05    --   47.76  77.00-180.00  192
 10  ω    106.00 178.00   0.50    0.17    --  107.31  98.00-119.00  144
 11  ω     92.00 178.00   0.50    0.17    --  107.31  57.00 -30.00  172
 12  ω     35.00 107.00   0.50    0.17    --  107.31 -77.00 120.00  144
 13  ω     35.00  68.00   0.50    0.17    --  107.31 -57.00  60.00   66
 14  ω     35.00  68.00   0.50    0.17    --  107.31 -57.00 -30.00   66
 15  ω     35.00  68.00   0.50    0.17    --  107.31 -57.00   0.00   66
 16  ω     35.00  68.00   0.50    0.17    --  107.31 -57.00  30.00   66
 17  ω    -27.00  29.00   0.50    0.05    --   47.76 -19.00-120.00  112
 18  ω     35.00  68.00   0.50    0.17    --  107.31 -57.00 -90.00   66
 19  ω     94.00 178.00   0.50    0.17    --  107.31  38.00-150.00  168
 20  ω     35.00  68.00   0.50    0.17    --  107.31 -57.00-180.00   66
 21  ω     35.00 111.00   0.50    0.17    --  107.31-125.00-150.00  152
 22  ω     35.00 106.00   0.50    0.17    --  107.31 -99.00-120.00  142
 23  ω     35.00 111.00   0.50    0.17    --  107.31-125.00   0.00  152
 24  ω     35.00 106.00   0.50    0.17    --  107.31 -99.00   0.00  142
 25  ω     -5.00  81.00   0.50    0.05    --   47.76 -98.00 133.00  172
 26  ω     35.00 111.00   0.50    0.17    --  107.31-125.00 120.00  152
 27  ω     35.00 106.00   0.50    0.17    --  107.31 -99.00  90.00  142
 28  ω     35.00 106.00   0.50    0.17    --  107.31 -98.00 133.00  142
 29  ω    -80.00  25.00   0.50    0.05    --  -47.76  98.00-119.00  210
 30  ω    -85.00 -19.00   0.50    0.17    --  -91.75 125.00 -90.00  132
 31  ω    -80.00 -19.00   0.50    0.17    --  -91.75  98.00-119.00  122
 32  ω   -163.00 -73.00   0.50    0.17    --  -91.75-125.00 120.00  180
 33  ω   -163.00 -86.00   0.50    0.17    --  -91.75 -98.00 133.00  154
 34  ω   -165.00 -78.00   0.50    0.17    --  -91.75 -38.00 150.00  174
 35  ω   -163.00 -69.00   0.50    0.17    --  -91.75 -77.00 120.00  188
 36  ω   -163.00 -69.00   0.50    0.17    --  -91.75 -77.00  30.00  188
 37  ω   -163.00 -69.00   0.50    0.17    --  -91.75 -77.00  60.00  188
 38  ω   -163.00 -69.00   0.50    0.17    --  -91.75 -77.00 -30.00  188
 39  ω   -163.00 -77.00   0.50    0.17    --  -91.75 -77.00 -60.00  172
 40  ω   -165.00 -78.00   0.50    0.17    --  -91.75 -38.00-120.00  174
 41  ω   -163.00 -77.00   0.50    0.17    --  -91.75 -57.00-150.00  172
 42  ω   -120.00 -33.00   0.50    0.05    --  -47.76 -57.00-150.00  174
 43  ω   -120.00 -25.00   0.50    0.05    --  -47.76 -77.00 -60.00  190
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0879774000
_diffrn_orient_matrix_UB_12      0.0033091000
_diffrn_orient_matrix_UB_13      0.1224082000
_diffrn_orient_matrix_UB_21      -0.0781862000
_diffrn_orient_matrix_UB_22      -0.1304124000
_diffrn_orient_matrix_UB_23      0.0159238000
_diffrn_orient_matrix_UB_31      0.2187487000
_diffrn_orient_matrix_UB_32      -0.0610154000
_diffrn_orient_matrix_UB_33      0.0427237000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3062
_reflns_number_total             3231
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.51a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.51a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.51a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.979
_refine_diff_density_min         -0.796
_refine_diff_density_rms         0.100
_refine_ls_extinction_coef       0.00122(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     374
_refine_ls_number_reflns         3231
_refine_ls_number_restraints     870
_refine_ls_R_factor_all          0.0328
_refine_ls_R_factor_gt           0.0303
_refine_ls_restrained_S_all      0.939
_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)+(0.0328P)²+0.8973P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0712
_refine_ls_wR_factor_ref         0.0737
_refine_special_details          
'In this structure the trans-1-(4-methylbenzoate)-2-(4-pyridyl)ethylene molecule was positionally disordered over two sites (A and B). The refined site occupancy for the A and B sites were 0.70 and 0.30, respectively. To model this disorder, SADI, SIMU and RIGU restraints were applied to the disordered sites.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O1A-C17A \\sim O1B-C17B
 with sigma of 0.02
 C17A-C18A \\sim C17B-C18B
 with sigma of 0.04
 O1A-C18A \\sim O1B-C18B
 with sigma of 0.02
 O2A-C17A \\sim O2B-C17B
 with sigma of 0.02
 N1-C4A \\sim N1-C4B
 with sigma of 0.02
 N1-C8A \\sim N1-C8B
 with sigma of 0.02
 C4A-C5A \\sim C4B-C5B
 with sigma of 0.02
 C11A-C13A \\sim C11B-C13B
 with sigma of 0.04
 C5A-C6A \\sim C5B-C6B
 with sigma of 0.02
 C12A-C16A \\sim C12B-C16B
 with sigma of 0.04
 C6A-C7A \\sim C6B-C7B
 with sigma of 0.02
 C6A-C9A \\sim C6B-C9B
 with sigma of 0.02
 C7A-C8A \\sim C7B-C8B
 with sigma of 0.02
 C9A-C11A \\sim C9B-C11B
 with sigma of 0.04
 C9A-C10A \\sim C9B-C10B
 with sigma of 0.02
 C10A-C12A \\sim C10B-C12B
 with sigma of 0.04
 C10A-C11A \\sim C10B-C11B
 with sigma of 0.02
 C13A-C17A \\sim C13B-C17B
 with sigma of 0.04
 C15A-C17A \\sim C15B-C17B
 with sigma of 0.04
 C11A-C12A \\sim C11B-C12B
 with sigma of 0.02
 C11A-C16A \\sim C11B-C16B
 with sigma of 0.02
 C6A-C10A \\sim C6B-C10B
 with sigma of 0.04
 C12A-C13A \\sim C12B-C13B
 with sigma of 0.02
 C7A-C9A \\sim C7B-C9B
 with sigma of 0.04
 C13A-C14A \\sim C13B-C14B
 with sigma of 0.02
 C10A-C16A \\sim C10B-C16B
 with sigma of 0.04
 C14A-C15A \\sim C14B-C15B
 with sigma of 0.02
 C14A-C17A \\sim C14B-C17B
 with sigma of 0.02
 C11A-C15A \\sim C11B-C15B
 with sigma of 0.04
 C15A-C16A \\sim C15B-C16B
 with sigma of 0.02
 C12A-C14A \\sim C12B-C14B
 with sigma of 0.04
 O1A-O2A \\sim O1B-O2B
 with sigma of 0.04
 C13A-C15A \\sim C13B-C15B
 with sigma of 0.04
 O1A-C14A \\sim O1B-C14B
 with sigma of 0.04
 C14A-C16A \\sim C14B-C16B
 with sigma of 0.04
 O2A-C14A \\sim O2B-C14B
 with sigma of 0.04
 N1-C5A \\sim N1-C5B
 with sigma of 0.04
 N1-C7A \\sim N1-C7B
 with sigma of 0.04
 C4A-C6A \\sim C4B-C6B
 with sigma of 0.04
 C5A-C7A \\sim C5B-C7B
 with sigma of 0.04
 C5A-C9A \\sim C5B-C9B
 with sigma of 0.04
 C6A-C8A \\sim C6B-C8B
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
O1A \\sim O1B \\sim O2A \\sim O2B \\sim N1 \\sim C4A \\sim C4B \\sim C5A \\sim
C5B \\sim C6A \\sim C6B \\sim C7A \\sim C7B \\sim C8A \\sim C8B \\sim C9A \\sim
C9B \\sim C10A \\sim C10B \\sim C11A \\sim C11B \\sim C12A \\sim C12B \\sim
C13A \\sim C13B \\sim C14A \\sim C14B \\sim C15A \\sim C15B \\sim C16A \\sim
C16B \\sim C17A \\sim C17B \\sim C18A \\sim C18B: within 2A with sigma of 0.02
and sigma for terminal atoms of 0.04 within 2A
4. Rigid body (RIGU) restrains
 O1A, O1B, O2A, O2B, N1, C4A, C4B, C5A, C5B, C6A, C6B, C7A, C7B, C8A, C8B, C9A,
  C9B, C10A, C10B, C11A, C11B, C12A, C12B, C13A, C13B, C14A, C14B, C15A, C15B,
 C16A, C16B, C17A, C17B, C18A, C18B
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Others
 Sof(O1B)=Sof(O2B)=Sof(C4B)=Sof(H4B)=Sof(C5B)=Sof(H5B)=Sof(C6B)=Sof(C7B)=
 Sof(H7B)=Sof(C8B)=Sof(H8B)=Sof(C9B)=Sof(H9B)=Sof(C10B)=Sof(H10B)=Sof(C11B)=
 Sof(C12B)=Sof(H12B)=Sof(C13B)=Sof(H13B)=Sof(C14B)=Sof(C15B)=Sof(H15B)=
 Sof(C16B)=Sof(H16B)=Sof(C17B)=Sof(C18B)=Sof(H18D)=Sof(H18E)=Sof(H18F)=1-FVAR(1)
 Sof(O1A)=Sof(O2A)=Sof(C4A)=Sof(H4A)=Sof(C5A)=Sof(H5A)=Sof(C6A)=Sof(C7A)=
 Sof(H7A)=Sof(C8A)=Sof(H8A)=Sof(C9A)=Sof(H9A)=Sof(C10A)=Sof(H10A)=Sof(C11A)=
 Sof(C12A)=Sof(H12A)=Sof(C13A)=Sof(H13A)=Sof(C14A)=Sof(C15A)=Sof(H15A)=
 Sof(C16A)=Sof(H16A)=Sof(C17A)=Sof(C18A)=Sof(H18A)=Sof(H18B)=Sof(H18C)=FVAR(1)
6.a Aromatic/amide H refined with riding coordinates:
 C4A(H4A), C4B(H4B), C5A(H5A), C5B(H5B), C7A(H7A), C7B(H7B), C8A(H8A),
 C8B(H8B), C9A(H9A), C9B(H9B), C10A(H10A), C10B(H10B), C12A(H12A), C12B(H12B),
 C13A(H13A), C13B(H13B), C15A(H15A), C15B(H15B), C16A(H16A), C16B(H16B)
6.b Idealised Me refined as rotating group:
 C18A(H18A,H18B,H18C), C18B(H18D,H18E,H18F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.69662(3) 0.59666(2) 0.76184(2) 0.02569(10) Uani 1 1 d . . . . .
F1 F 1.1770(3) 0.4633(2) 0.79556(18) 0.0287(5) Uani 1 1 d . . . . .
F2 F 1.4073(3) 0.38956(19) 0.97535(19) 0.0280(5) Uani 1 1 d . . . . .
C1 C 0.8768(5) 0.5393(3) 0.9036(3) 0.0235(7) Uani 1 1 d . . . . .
C2 C 1.0863(6) 0.4829(3) 0.8965(3) 0.0244(7) Uani 1 1 d . . . . .
C3 C 1.2054(5) 0.4446(3) 0.9893(3) 0.0225(7) Uani 1 1 d . . . . .
O1A O 1.4363(18) 0.0458(13) 1.2520(7) 0.0258(17) Uani 0.698(6) 1 d D U P A 1
O1B O 1.145(4) 0.064(4) 1.3400(18) 0.028(3) Uani 0.302(6) 1 d D U P A 2
O2A O 1.1081(18) 0.0758(19) 1.3410(9) 0.039(2) Uani 0.698(6) 1 d D U P A 1
O2B O 1.453(4) 0.030(3) 1.2332(17) 0.020(3) Uani 0.302(6) 1 d D U P A 2
N1 N 0.5367(5) 0.3345(3) 0.4337(3) 0.0291(6) Uani 1 1 d D U . . .
C4A C 0.7360(17) 0.2905(18) 0.4342(9) 0.0299(16) Uani 0.698(6) 1 d D U P A 1
H4A H 0.807214 0.283723 0.362747 0.036 Uiso 0.698(6) 1 calc R U P A 1
C4B C 0.406(3) 0.354(2) 0.5134(12) 0.028(2) Uani 0.302(6) 1 d D U P A 2
H4B H 0.261532 0.385247 0.498497 0.033 Uiso 0.302(6) 1 calc R U P A 2
C5A C 0.8606(12) 0.2516(9) 0.5268(6) 0.0293(14) Uani 0.698(6) 1 d D U P A 1
H5A H 1.004951 0.215816 0.517690 0.035 Uiso 0.698(6) 1 calc R U P A 1
C5B C 0.464(2) 0.3308(14) 0.6222(12) 0.025(2) Uani 0.302(6) 1 d D U P A 2
H5B H 0.363036 0.347167 0.681937 0.030 Uiso 0.302(6) 1 calc R U P A 2
C6A C 0.7690(10) 0.2662(5) 0.6335(4) 0.0231(11) Uani 0.698(6) 1 d D U P A 1
C6B C 0.677(2) 0.2826(12) 0.6435(9) 0.018(2) Uani 0.302(6) 1 d D U P A 2
C7A C 0.5534(13) 0.3182(6) 0.6371(5) 0.0258(11) Uani 0.698(6) 1 d D U P A 1
H7A H 0.481897 0.331292 0.706791 0.031 Uiso 0.698(6) 1 calc R U P A 1
C7B C 0.819(3) 0.2633(19) 0.5515(12) 0.023(2) Uani 0.302(6) 1 d D U P A 2
H7B H 0.966634 0.237161 0.563203 0.028 Uiso 0.302(6) 1 calc R U P A 2
C8A C 0.4456(11) 0.3502(9) 0.5406(6) 0.0290(12) Uani 0.698(6) 1 d D U P A 1
H8A H 0.300047 0.385215 0.546289 0.035 Uiso 0.698(6) 1 calc R U P A 1
C8B C 0.752(4) 0.281(4) 0.4437(19) 0.030(3) Uani 0.302(6) 1 d D U P A 2
H8B H 0.841965 0.259351 0.382120 0.036 Uiso 0.302(6) 1 calc R U P A 2
C9A C 0.8949(9) 0.2270(5) 0.7332(5) 0.0280(11) Uani 0.698(6) 1 d D U P A 1
H9A H 1.042367 0.198183 0.720695 0.034 Uiso 0.698(6) 1 calc R U P A 1
C9B C 0.7440(16) 0.2542(10) 0.7588(8) 0.0185(18) Uani 0.302(6) 1 d D U P A 2
H9B H 0.638378 0.273310 0.815707 0.022 Uiso 0.302(6) 1 calc R U P A 2
C10A C 0.8205(8) 0.2283(5) 0.8390(4) 0.0246(10) Uani 0.698(6) 1 d D U P A 1
H10A H 0.673268 0.258517 0.849871 0.029 Uiso 0.698(6) 1 calc R U P A 1
C10B C 0.9362(17) 0.2046(10) 0.7932(10) 0.0185(19) Uani 0.302(6) 1 d D U P A 2
H10B H 1.041295 0.185094 0.736131 0.022 Uiso 0.302(6) 1 calc R U P A 2
C11A C 0.9384(10) 0.1888(5) 0.9413(5) 0.0215(11) Uani 0.698(6) 1 d D U P A 1
C11B C 1.006(2) 0.1762(12) 0.9096(10) 0.016(2) Uani 0.302(6) 1 d D U P A 2
C12A C 0.8254(10) 0.1960(6) 1.0452(6) 0.0255(12) Uani 0.698(6) 1 d D U P A 1
H12A H 0.677617 0.227567 1.046816 0.031 Uiso 0.698(6) 1 calc R U P A 1
C12B C 1.217(2) 0.1261(18) 0.9305(13) 0.019(2) Uani 0.302(6) 1 d D U P A 2
H12B H 1.315420 0.111434 0.869103 0.023 Uiso 0.302(6) 1 calc R U P A 2
C13A C 0.9227(12) 0.1586(9) 1.1444(6) 0.0247(12) Uani 0.698(6) 1 d D U P A 1
H13A H 0.842811 0.163183 1.214423 0.030 Uiso 0.698(6) 1 calc R U P A 1
C13B C 1.284(4) 0.097(5) 1.0383(18) 0.020(3) Uani 0.302(6) 1 d D U P A 2
H13B H 1.430652 0.067154 1.048344 0.024 Uiso 0.302(6) 1 calc R U P A 2
C14A C 1.139(2) 0.114(2) 1.1422(8) 0.0222(14) Uani 0.698(6) 1 d D U P A 1
C14B C 1.147(5) 0.111(6) 1.1331(18) 0.022(3) Uani 0.302(6) 1 d D U P A 2
C15A C 1.2567(18) 0.107(2) 1.0394(9) 0.0248(17) Uani 0.698(6) 1 d D U P A 1
H15A H 1.405452 0.077993 1.038281 0.030 Uiso 0.698(6) 1 calc R U P A 1
C15B C 0.932(3) 0.162(2) 1.1099(11) 0.023(2) Uani 0.302(6) 1 d D U P A 2
H15B H 0.832073 0.173356 1.171601 0.028 Uiso 0.302(6) 1 calc R U P A 2
C16A C 1.1566(11) 0.1436(8) 0.9396(6) 0.0232(13) Uani 0.698(6) 1 d D U P A 1
H16A H 1.235931 0.137759 0.869750 0.028 Uiso 0.698(6) 1 calc R U P A 1
C16B C 0.864(2) 0.1960(12) 1.0013(12) 0.018(2) Uani 0.302(6) 1 d D U P A 2
H16B H 0.720534 0.232519 0.989434 0.021 Uiso 0.302(6) 1 calc R U P A 2
C17A C 1.2214(12) 0.0755(11) 1.2547(5) 0.0257(13) Uani 0.698(6) 1 d D U P A 1
C17B C 1.260(3) 0.068(3) 1.2398(12) 0.025(3) Uani 0.302(6) 1 d D U P A 2
C18A C 1.5306(11) 0.0128(6) 1.3553(5) 0.0408(15) Uani 0.698(6) 1 d D U P A 1
H18A H 1.685846 -0.008639 1.341619 0.061 Uiso 0.698(6) 1 calc R U P A 1
H18B H 1.465504 -0.059512 1.404370 0.061 Uiso 0.698(6) 1 calc R U P A 1
H18C H 1.506317 0.083298 1.392403 0.061 Uiso 0.698(6) 1 calc R U P A 1
C18B C 1.250(2) 0.0417(15) 1.4396(11) 0.043(3) Uani 0.302(6) 1 d D U P A 2
H18D H 1.341290 0.108930 1.435234 0.065 Uiso 0.302(6) 1 calc R U P A 2
H18E H 1.339034 -0.038407 1.448860 0.065 Uiso 0.302(6) 1 calc R U P A 2
H18F H 1.142292 0.038965 1.504662 0.065 Uiso 0.302(6) 1 calc R U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 2.095(4) . ?
I1 N1 2.831(3) 2_666 ?
F1 C2 1.352(4) . ?
F2 C3 1.350(4) . ?
C1 C2 1.388(5) . ?
C1 C3 1.394(5) 2_767 ?
C2 C3 1.376(5) . ?
O1A C17A 1.347(10) . ?
O1A C18A 1.400(11) . ?
O1B C17B 1.344(17) . ?
O1B C18B 1.40(2) . ?
O2A C17A 1.205(10) . ?
O2B C17B 1.233(17) . ?
N1 C4A 1.286(10) . ?
N1 C4B 1.244(15) . ?
N1 C8A 1.405(8) . ?
N1 C8B 1.412(18) . ?
C4A H4A 0.9500 . ?
C4A C5A 1.395(10) . ?
C4B H4B 0.9500 . ?
C4B C5B 1.370(15) . ?
C5A H5A 0.9500 . ?
C5A C6A 1.400(7) . ?
C5B H5B 0.9500 . ?
C5B C6B 1.401(14) . ?
C6A C7A 1.405(8) . ?
C6A C9A 1.470(8) . ?
C6B C7B 1.398(14) . ?
C6B C9B 1.461(12) . ?
C7A H7A 0.9500 . ?
C7A C8A 1.372(9) . ?
C7B H7B 0.9500 . ?
C7B C8B 1.385(18) . ?
C8A H8A 0.9500 . ?
C8B H8B 0.9500 . ?
C9A H9A 0.9500 . ?
C9A C10A 1.325(7) . ?
C9B H9B 0.9500 . ?
C9B C10B 1.330(13) . ?
C10A H10A 0.9500 . ?
C10A C11A 1.468(7) . ?
C10B H10B 0.9500 . ?
C10B C11B 1.480(13) . ?
C11A C12A 1.397(8) . ?
C11A C16A 1.399(8) . ?
C11B C12B 1.394(13) . ?
C11B C16B 1.396(14) . ?
C12A H12A 0.9500 . ?
C12A C13A 1.366(9) . ?
C12B H12B 0.9500 . ?
C12B C13B 1.376(17) . ?
C13A H13A 0.9500 . ?
C13A C14A 1.384(12) . ?
C13B H13B 0.9500 . ?
C13B C14B 1.39(2) . ?
C14A C15A 1.397(11) . ?
C14A C17A 1.467(7) . ?
C14B C15B 1.43(2) . ?
C14B C17B 1.497(13) . ?
C15A H15A 0.9500 . ?
C15A C16A 1.381(10) . ?
C15B H15B 0.9500 . ?
C15B C16B 1.388(15) . ?
C16A H16A 0.9500 . ?
C16B H16B 0.9500 . ?
C18A H18A 0.9800 . ?
C18A H18B 0.9800 . ?
C18A H18C 0.9800 . ?
C18B H18D 0.9800 . ?
C18B H18E 0.9800 . ?
C18B H18F 0.9800 . ?

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
C1 I1 N1 177.46(11) . 2_666 ?
C2 C1 I1 121.9(3) . . ?
C2 C1 C3 115.8(3) . 2_767 ?
C3 C1 I1 122.3(2) 2_767 . ?
F1 C2 C1 119.3(3) . . ?
F1 C2 C3 118.4(3) . . ?
C3 C2 C1 122.2(3) . . ?
F2 C3 C1 119.5(3) . 2_767 ?
F2 C3 C2 118.5(3) . . ?
C2 C3 C1 122.0(3) . 2_767 ?
C17A O1A C18A 117.7(7) . . ?
C17B O1B C18B 120.2(17) . . ?
C4A N1 C8A 113.0(6) . . ?
C4B N1 C8B 125.6(11) . . ?
N1 C4A H4A 116.0 . . ?
N1 C4A C5A 128.0(9) . . ?
C5A C4A H4A 116.0 . . ?
N1 C4B H4B 119.2 . . ?
N1 C4B C5B 121.7(13) . . ?
C5B C4B H4B 119.2 . . ?
C4A C5A H5A 120.6 . . ?
C4A C5A C6A 118.8(7) . . ?
C6A C5A H5A 120.6 . . ?
C4B C5B H5B 120.7 . . ?
C4B C5B C6B 118.7(12) . . ?
C6B C5B H5B 120.7 . . ?
C5A C6A C7A 115.6(5) . . ?
C5A C6A C9A 120.6(6) . . ?
C7A C6A C9A 123.8(5) . . ?
C5B C6B C9B 120.3(11) . . ?
C7B C6B C5B 117.9(10) . . ?
C7B C6B C9B 121.8(12) . . ?
C6A C7A H7A 119.9 . . ?
C8A C7A C6A 120.3(5) . . ?
C8A C7A H7A 119.9 . . ?
C6B C7B H7B 119.1 . . ?
C8B C7B C6B 121.9(15) . . ?
C8B C7B H7B 119.1 . . ?
N1 C8A H8A 117.9 . . ?
C7A C8A N1 124.2(6) . . ?
C7A C8A H8A 117.9 . . ?
N1 C8B H8B 123.1 . . ?
C7B C8B N1 113.9(17) . . ?
C7B C8B H8B 123.1 . . ?
C6A C9A H9A 117.1 . . ?
C10A C9A C6A 125.7(5) . . ?
C10A C9A H9A 117.1 . . ?
C6B C9B H9B 116.2 . . ?
C10B C9B C6B 127.5(11) . . ?
C10B C9B H9B 116.2 . . ?
C9A C10A H10A 116.1 . . ?
C9A C10A C11A 127.8(5) . . ?
C11A C10A H10A 116.1 . . ?
C9B C10B H10B 116.1 . . ?
C9B C10B C11B 127.9(10) . . ?
C11B C10B H10B 116.1 . . ?
C12A C11A C10A 117.9(5) . . ?
C12A C11A C16A 118.9(5) . . ?
C16A C11A C10A 123.2(6) . . ?
C12B C11B C10B 120.4(11) . . ?
C12B C11B C16B 118.3(10) . . ?
C16B C11B C10B 121.3(10) . . ?
C11A C12A H12A 119.3 . . ?
C13A C12A C11A 121.4(5) . . ?
C13A C12A H12A 119.3 . . ?
C11B C12B H12B 119.4 . . ?
C13B C12B C11B 121.3(13) . . ?
C13B C12B H12B 119.4 . . ?
C12A C13A H13A 120.3 . . ?
C12A C13A C14A 119.4(6) . . ?
C14A C13A H13A 120.3 . . ?
C12B C13B H13B 118.6 . . ?
C12B C13B C14B 122.8(15) . . ?
C14B C13B H13B 118.6 . . ?
C13A C14A C15A 120.5(6) . . ?
C13A C14A C17A 113.7(9) . . ?
C15A C14A C17A 125.8(9) . . ?
C13B C14B C15B 114.9(12) . . ?
C13B C14B C17B 111.6(18) . . ?
C15B C14B C17B 133(2) . . ?
C14A C15A H15A 120.1 . . ?
C16A C15A C14A 119.8(7) . . ?
C16A C15A H15A 120.1 . . ?
C14B C15B H15B 118.4 . . ?
C16B C15B C14B 123.1(13) . . ?
C16B C15B H15B 118.4 . . ?
C11A C16A H16A 120.0 . . ?
C15A C16A C11A 120.0(6) . . ?
C15A C16A H16A 120.0 . . ?
C11B C16B H16B 120.2 . . ?
C15B C16B C11B 119.5(11) . . ?
C15B C16B H16B 120.2 . . ?
O1A C17A C14A 113.8(8) . . ?
O2A C17A O1A 123.3(6) . . ?
O2A C17A C14A 122.8(8) . . ?
O1B C17B C14B 119.0(16) . . ?
O2B C17B O1B 122.0(13) . . ?
O2B C17B C14B 118.9(16) . . ?
O1A C18A H18A 109.5 . . ?
O1A C18A H18B 109.5 . . ?
O1A C18A H18C 109.5 . . ?
H18A C18A H18B 109.5 . . ?
H18A C18A H18C 109.5 . . ?
H18B C18A H18C 109.5 . . ?
O1B C18B H18D 109.5 . . ?
O1B C18B H18E 109.5 . . ?
O1B C18B H18F 109.5 . . ?
H18D C18B H18E 109.5 . . ?
H18D C18B H18F 109.5 . . ?
H18E C18B H18F 109.5 . . ?

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
I1 C1 C2 F1 -0.5(4) . . . . ?
I1 C1 C2 C3 -179.8(2) . . . . ?
F1 C2 C3 F2 0.1(4) . . . . ?
F1 C2 C3 C1 -179.6(3) . . . 2_767 ?
C1 C2 C3 F2 179.4(3) . . . . ?
C1 C2 C3 C1 -0.3(6) . . . 2_767 ?
C3 C1 C2 F1 179.6(3) 2_767 . . . ?
C3 C1 C2 C3 0.3(5) 2_767 . . . ?
N1 C4A C5A C6A -4(2) . . . . ?
N1 C4B C5B C6B -1(3) . . . . ?
C4A N1 C8A C7A -2.2(14) . . . . ?
C4A C5A C6A C7A 1.1(13) . . . . ?
C4A C5A C6A C9A -179.7(11) . . . . ?
C4B N1 C8B C7B -7(5) . . . . ?
C4B C5B C6B C7B 1(2) . . . . ?
C4B C5B C6B C9B -178.6(14) . . . . ?
C5A C6A C7A C8A 0.5(9) . . . . ?
C5A C6A C9A C10A -175.0(6) . . . . ?
C5B C6B C7B C8B -5(3) . . . . ?
C5B C6B C9B C10B 177.6(12) . . . . ?
C6A C7A C8A N1 0.1(11) . . . . ?
C6A C9A C10A C11A 179.2(5) . . . . ?
C6B C7B C8B N1 7(5) . . . . ?
C6B C9B C10B C11B 179.6(12) . . . . ?
C7A C6A C9A C10A 4.1(9) . . . . ?
C7B C6B C9B C10B -2.5(19) . . . . ?
C8A N1 C4A C5A 4(2) . . . . ?
C8B N1 C4B C5B 4(4) . . . . ?
C9A C6A C7A C8A -178.7(6) . . . . ?
C9A C10A C11A C12A -178.7(6) . . . . ?
C9A C10A C11A C16A 0.8(9) . . . . ?
C9B C6B C7B C8B 175(3) . . . . ?
C9B C10B C11B C12B -178.8(13) . . . . ?
C9B C10B C11B C16B 2.7(19) . . . . ?
C10A C11A C12A C13A 178.7(6) . . . . ?
C10A C11A C16A C15A -179.6(12) . . . . ?
C10B C11B C12B C13B -179(3) . . . . ?
C10B C11B C16B C15B 176.6(14) . . . . ?
C11A C12A C13A C14A 0.8(16) . . . . ?
C11B C12B C13B C14B 3(5) . . . . ?
C12A C11A C16A C15A -0.2(14) . . . . ?
C12A C13A C14A C15A 0(3) . . . . ?
C12A C13A C14A C17A -179.1(13) . . . . ?
C12B C11B C16B C15B -2(2) . . . . ?
C12B C13B C14B C15B -3(7) . . . . ?
C12B C13B C14B C17B 178(5) . . . . ?
C13A C14A C15A C16A -1(3) . . . . ?
C13A C14A C17A O1A -172.8(15) . . . . ?
C13A C14A C17A O2A 4(3) . . . . ?
C13B C14B C15B C16B 0(6) . . . . ?
C13B C14B C17B O1B -174(4) . . . . ?
C13B C14B C17B O2B 1(6) . . . . ?
C14A C15A C16A C11A 1(2) . . . . ?
C14B C15B C16B C11B 2(4) . . . . ?
C15A C14A C17A O1A 8(3) . . . . ?
C15A C14A C17A O2A -174.9(18) . . . . ?
C15B C14B C17B O1B 7(8) . . . . ?
C15B C14B C17B O2B -178(5) . . . . ?
C16A C11A C12A C13A -0.8(9) . . . . ?
C16B C11B C12B C13B 0(3) . . . . ?
C17A C14A C15A C16A 178(2) . . . . ?
C17B C14B C15B C16B 179(5) . . . . ?
C18A O1A C17A O2A 0.5(19) . . . . ?
C18A O1A C17A C14A 177.4(16) . . . . ?
C18B O1B C17B O2B 14(5) . . . . ?
C18B O1B C17B C14B -171(4) . . . . ?

_olex2_exptl_crystal_mounting_method 'MiTeGen 50 micron MicroLoop'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_diffrn_reflns_filtered   591
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.967
_oxdiff_exptl_absorpt_empirical_full_min 0.605
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Toluene'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_GMF21028
_database_code_depnum_ccdc_archive 'CCDC 2156802'
loop_
_audit_author_name
_audit_author_address
'Gregory Ferrence'
;Illinois State University
United States of America
;
_audit_update_record             
;
2022-03-04 deposited with the CCDC.	2022-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
'hemikis(1,2,4,5-tetrachloro-3,6-diiodobenzene) methyl 4-[(1E)-2-(pyridin-4-yl)ethenyl]benzoate'
_chemical_name_common            ?
_chemical_melting_point          ?
_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

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.2756(2)
_cell_length_b                   10.2186(3)
_cell_length_c                   11.8757(4)
_cell_angle_alpha                114.5720(10)
_cell_angle_beta                 92.194(2)
_cell_angle_gamma                107.358(2)
_cell_volume                     856.35(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9882
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      32.72

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.835
_exptl_crystal_F_000             462
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    2.192
_shelx_estimated_absorpt_T_min   0.600
_shelx_estimated_absorpt_T_max   0.735
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6770
_exptl_absorpt_correction_T_max  0.7465
_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_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD diffractometer'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_measurement_details      
;
 A total of 3672 frames were collected.  
 The total exposure time was 5.10 hours.
;
_diffrn_reflns_number            32790
_diffrn_reflns_av_unetI/netI     0.0127
_diffrn_reflns_av_R_equivalents  0.0176
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.919
_diffrn_reflns_theta_max         32.927
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6056
_reflns_number_gt                5711
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX4 (Bruker, 2021)'
_computing_cell_refinement       'APEX4 & SAINT (Bruker, 2021)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015b)'
_computing_molecular_graphics    
;
Mercury CSD (Macrae et al., 2020)
;
_computing_publication_material  
;
;

_refine_special_details          
;
All non-H atoms were refined anisotropically.  All H 
atoms were identifiable in the difference Fourier, but 
were included in the final refinement using 
the riding-model approximation.
d(C--H) = 
0.95 Å Uiso = 1.2Ueq (C) for aromatic, 
and
0.98 Å , Uiso = 1.5Ueq (C) for methyl 
H atoms. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0149P)²+0.5237P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6056
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0185
_refine_ls_R_factor_gt           0.0162
_refine_ls_wR_factor_ref         0.0388
_refine_ls_wR_factor_gt          0.0377
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_restrained_S_all      1.110
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

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 . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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_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_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) . . . . ?

_refine_diff_density_max         0.752
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.073

