# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_sfull_a
_audit_block_doi                 10.5517/ccdc.csd.cc2fhswm
_database_code_depnum_ccdc_archive 'CCDC 2249511'
loop_
_citation_id
_citation_doi
_citation_year
1 10.26434/chemrxiv-2023-wnhrf 2023
loop_
_audit_author_name
_audit_author_address
'Jogirdas Vainauskas'
;McGill University, University of Birmingham
Canada
;
_audit_update_record             
;
2023-04-25 deposited with the CCDC.	2023-10-09 downloaded from the CCDC.
;
_audit_creation_date             2021-12-02
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H10, 2(C6 F4 I2)'
_chemical_formula_sum            'C26 H10 F8 I4'
_chemical_formula_weight         981.94
_chemical_melting_point          ?
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'

_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                   5.9679(8)
_cell_length_b                   9.6419(13)
_cell_length_c                   12.2058(16)
_cell_angle_alpha                73.039(5)
_cell_angle_beta                 89.800(5)
_cell_angle_gamma                81.559(5)
_cell_volume                     663.94(15)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    7323
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      72.64
_cell_measurement_theta_min      3.79
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    37.522
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.1708
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Krause, Herbst-Irmer, Sheldrick & Stalke, 2015)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.456
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             450
_exptl_crystal_preparation       Luminescent
_exptl_crystal_size_max          0.352
_exptl_crystal_size_mid          0.145
_exptl_crystal_size_min          0.055
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0571
_diffrn_reflns_av_unetI/netI     0.0533
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9449
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.634
_diffrn_reflns_theta_min         4.852
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  
'Bruker D8 Venture, Dual, Cu at zero, PHOTON II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2298
_reflns_number_total             2574
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         1.270
_refine_diff_density_min         -1.671
_refine_diff_density_rms         0.275
_refine_ls_extinction_coef       0.0055(9)
_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   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2574
_refine_ls_number_restraints     117
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0590
_refine_ls_restrained_S_all      1.014
_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)+(0.1255P)²+1.7250P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1599
_refine_ls_wR_factor_ref         0.1708
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Aromatic/amide H refined with riding coordinates:
 C2B(H2B), C6B(H6B), C4B(H4B), C5B(H5B), C7B(H7B)
;
_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
I1A I 0.78353(8) 0.82966(5) 0.65689(4) 0.0373(3) Uani 1 1 d . . . . .
I2A I 0.18449(7) 0.65539(5) 0.23940(4) 0.0386(3) Uani 1 1 d . . . . .
F1A F 0.1443(8) 0.5827(6) 0.5105(4) 0.0480(11) Uani 1 1 d . . . . .
F3A F 0.8256(8) 0.9045(6) 0.3845(4) 0.0483(12) Uani 1 1 d . . . . .
F4A F 0.5951(8) 0.8376(6) 0.2261(4) 0.0471(11) Uani 1 1 d . . . . .
F2A F 0.3695(8) 0.6536(6) 0.6687(4) 0.0427(11) Uani 1 1 d . . . . .
C6A C 0.3094(11) 0.6625(7) 0.4783(6) 0.0284(13) Uani 1 1 d . . . . .
C4A C 0.6064(11) 0.7789(7) 0.5312(6) 0.0273(12) Uani 1 1 d . . . . .
C5A C 0.4273(11) 0.6980(7) 0.5612(6) 0.0302(13) Uani 1 1 d . . . . .
C1A C 0.3642(11) 0.7083(7) 0.3641(6) 0.0282(12) Uani 1 1 d . . . . .
C3A C 0.6567(11) 0.8236(8) 0.4186(6) 0.0296(13) Uani 1 1 d . . . . .
C2A C 0.5381(11) 0.7877(7) 0.3356(6) 0.0307(13) Uani 1 1 d . . . . .
C2B C 1.2064(11) 0.4989(8) -0.0536(5) 0.0324(13) Uani 1 1 d . . . . .
H2B H 1.343862 0.497539 -0.089672 0.039 Uiso 1 1 calc R U . . .
C1B C 1.1341(12) 0.3646(8) 0.0024(5) 0.0319(13) Uani 1 1 d . . . . .
C3B C 1.0831(12) 0.6310(8) -0.0573(5) 0.0318(13) Uani 1 1 d . . . . .
C6B C 0.8132(14) 0.9009(8) -0.0603(6) 0.0422(16) Uani 1 1 d . . . . .
H6B H 0.726757 0.990163 -0.062191 0.051 Uiso 1 1 calc R U . . .
C4B C 1.1564(13) 0.7684(8) -0.1132(6) 0.0382(15) Uani 1 1 d . . . . .
H4B H 1.293866 0.769339 -0.149386 0.046 Uiso 1 1 calc R U . . .
C5B C 1.0266(15) 0.8985(8) -0.1142(6) 0.0432(16) Uani 1 1 d . . . . .
H5B H 1.077891 0.986404 -0.150475 0.052 Uiso 1 1 calc R U . . .
C7B C 0.7366(13) 0.7734(8) -0.0064(6) 0.0367(14) Uani 1 1 d . . . . .
H7B H 0.597714 0.776154 0.028321 0.044 Uiso 1 1 calc R U . . .


_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
I1A C4A 2.077(7) . ?
I2A C1A 2.086(7) . ?
F1A C6A 1.327(8) . ?
F3A C3A 1.355(8) . ?
F4A C2A 1.344(8) . ?
F2A C5A 1.317(8) . ?
C6A C5A 1.383(11) . ?
C6A C1A 1.388(10) . ?
C4A C5A 1.400(10) . ?
C4A C3A 1.362(10) . ?
C1A C2A 1.364(9) . ?
C3A C2A 1.388(10) . ?
C2B H2B 0.9300 . ?
C2B C1B 1.406(10) . ?
C2B C3B 1.363(10) . ?
C1B C3B 1.458(9) 2_765 ?
C1B C7B 1.424(10) 2_765 ?
C3B C4B 1.433(9) . ?
C6B H6B 0.9300 . ?
C6B C5B 1.432(12) . ?
C6B C7B 1.359(11) . ?
C4B H4B 0.9300 . ?
C4B C5B 1.371(11) . ?
C5B H5B 0.9300 . ?
C7B H7B 0.9300 . ?

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
F1A C6A C5A 118.6(6) . . ?
F1A C6A C1A 120.7(6) . . ?
C5A C6A C1A 120.7(6) . . ?
C5A C4A I1A 119.8(5) . . ?
C3A C4A I1A 122.0(5) . . ?
C3A C4A C5A 118.2(6) . . ?
F2A C5A C6A 119.0(6) . . ?
F2A C5A C4A 120.7(7) . . ?
C6A C5A C4A 120.3(7) . . ?
C6A C1A I2A 120.5(5) . . ?
C2A C1A I2A 121.0(5) . . ?
C2A C1A C6A 118.5(6) . . ?
F3A C3A C4A 120.6(6) . . ?
F3A C3A C2A 118.1(6) . . ?
C4A C3A C2A 121.3(6) . . ?
F4A C2A C1A 121.0(6) . . ?
F4A C2A C3A 118.0(6) . . ?
C1A C2A C3A 121.0(6) . . ?
C1B C2B H2B 118.7 . . ?
C3B C2B H2B 118.7 . . ?
C3B C2B C1B 122.7(6) . . ?
C2B C1B C3B 117.8(6) . 2_765 ?
C2B C1B C7B 122.6(6) . 2_765 ?
C7B C1B C3B 119.6(6) 2_765 2_765 ?
C2B C3B C1B 119.5(6) . 2_765 ?
C2B C3B C4B 123.1(6) . . ?
C4B C3B C1B 117.5(7) . 2_765 ?
C5B C6B H6B 119.9 . . ?
C7B C6B H6B 119.9 . . ?
C7B C6B C5B 120.2(7) . . ?
C3B C4B H4B 119.6 . . ?
C5B C4B C3B 120.9(7) . . ?
C5B C4B H4B 119.6 . . ?
C6B C5B H5B 119.5 . . ?
C4B C5B C6B 121.0(7) . . ?
C4B C5B H5B 119.5 . . ?
C1B C7B H7B 119.5 2_765 . ?
C6B C7B C1B 120.9(7) . 2_765 ?
C6B C7B H7B 119.5 . . ?

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
I1A C4A C5A F2A 0.0(9) . . . . ?
I1A C4A C5A C6A -179.5(5) . . . . ?
I1A C4A C3A F3A -0.4(9) . . . . ?
I1A C4A C3A C2A 179.4(5) . . . . ?
I2A C1A C2A F4A 1.8(9) . . . . ?
I2A C1A C2A C3A 179.6(5) . . . . ?
F1A C6A C5A F2A -1.1(10) . . . . ?
F1A C6A C5A C4A 178.4(6) . . . . ?
F1A C6A C1A I2A 1.0(9) . . . . ?
F1A C6A C1A C2A -178.8(6) . . . . ?
F3A C3A C2A F4A -1.2(10) . . . . ?
F3A C3A C2A C1A -179.1(6) . . . . ?
C6A C1A C2A F4A -178.5(6) . . . . ?
C6A C1A C2A C3A -0.6(10) . . . . ?
C4A C3A C2A F4A 179.0(6) . . . . ?
C4A C3A C2A C1A 1.1(11) . . . . ?
C5A C6A C1A I2A -179.6(5) . . . . ?
C5A C6A C1A C2A 0.6(10) . . . . ?
C5A C4A C3A F3A 178.8(6) . . . . ?
C5A C4A C3A C2A -1.4(11) . . . . ?
C1A C6A C5A F2A 179.5(6) . . . . ?
C1A C6A C5A C4A -1.0(11) . . . . ?
C3A C4A C5A F2A -179.2(6) . . . . ?
C3A C4A C5A C6A 1.4(10) . . . . ?
C2B C3B C4B C5B -179.8(7) . . . . ?
C1B C2B C3B C1B -0.8(11) . . . 2_765 ?
C1B C2B C3B C4B 179.4(7) . . . . ?
C1B C3B C4B C5B 0.4(11) 2_765 . . . ?
C3B C2B C1B C3B 0.7(11) . . . 2_765 ?
C3B C2B C1B C7B -179.8(6) . . . 2_765 ?
C3B C4B C5B C6B -0.6(11) . . . . ?
C5B C6B C7B C1B 0.0(11) . . . 2_765 ?
C7B C6B C5B C4B 0.4(11) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DCM'
####################################################################### 
# 
# 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_sfull_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2240201'
loop_
_audit_author_name
_audit_author_address
'Jogirdas Vainauskas'
;McGill University, University of Birmingham
Canada
;
_audit_update_record             
;
2023-04-25 deposited with the CCDC.	2023-10-09 downloaded from the CCDC.
;
_audit_creation_date             2022-01-13
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
# start Validation Reply Form
_vrf_PLAT213_sfull_a             
;
PROBLEM: Atom C14B            has ADP max/min Ratio .....        4.5 oblate
RESPONSE: This is most likely due to thermal motion, resulting from 
data collection at room temperature. 
;
# end Validation Reply Form
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C60, 2(C6 F4 I2)'
_chemical_formula_sum            'C72 F8 I4'
_chemical_formula_weight         1524.32
_chemical_melting_point          ?
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'
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'

_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      orthorhombic
_space_group_IT_number           64
_space_group_name_H-M_alt        'C m c e'
_space_group_name_Hall           '-C 2bc 2'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y+1/2, z+1/2'
'-x, y+1/2, -z+1/2'
'x, -y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1, z+1/2'
'-x+1/2, y+1, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x, y-1/2, -z-1/2'
'x, -y-1/2, z-1/2'
'-x, y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, y, -z-1/2'
'x+1/2, -y, z-1/2'
'-x+1/2, y+1/2, z'

_cell_length_a                   24.9493(4)
_cell_length_b                   17.2771(3)
_cell_length_c                   10.18670(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4390.99(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9876
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      72.47
_cell_measurement_theta_min      5.12
_shelx_estimated_absorpt_T_max   0.223
_shelx_estimated_absorpt_T_min   0.048
_exptl_absorpt_coefficient_mu    23.071
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.3927
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1839 before and 0.0831 after correction.
The Ratio of minimum to maximum transmission is 0.1781.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    2.306
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2864
_exptl_crystal_size_max          0.334
_exptl_crystal_size_mid          0.151
_exptl_crystal_size_min          0.093
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0678
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            35985
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.468
_diffrn_reflns_theta_min         3.543
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'micro-focus sealed X-ray tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1812
_reflns_number_total             2236
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         1.097
_refine_diff_density_min         -0.747
_refine_diff_density_rms         0.131
_refine_ls_extinction_coef       0.00021(3)
_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   1.094
_refine_ls_hydrogen_treatment    undef
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         2236
_refine_ls_number_restraints     171
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0434
_refine_ls_restrained_S_all      1.089
_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)+(0.0561P)²+33.8763P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1103
_refine_ls_wR_factor_ref         0.1282
_refine_special_details          ?
_olex2_refinement_description    
;
1. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
;
_atom_sites_solution_hydrogens   .
_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
C00A C 0.5287(4) 0.3066(3) 0.5820(10) 0.086(2) Uani 1 1 d . . . . .
F1A F 0.71804(15) 0.5197(2) 0.1459(4) 0.0603(9) Uani 1 1 d . . . . .
I1A I 0.66110(2) 0.65460(2) -0.01315(4) 0.0550(2) Uani 1 1 d . . . . .
F2A F 0.71510(15) 0.79250(19) 0.1508(4) 0.0623(9) Uani 1 1 d . . . . .
C1A C 0.7329(2) 0.5873(3) 0.1958(5) 0.0439(11) Uani 1 1 d . . . . .
C2A C 0.7148(2) 0.6562(3) 0.1436(5) 0.0432(11) Uani 1 1 d . . . . .
C3A C 0.7322(2) 0.7240(3) 0.1978(5) 0.0437(11) Uani 1 1 d . . . . .
C1B C 0.5248(4) 0.3840(6) 0.7783(9) 0.108(3) Uani 1 1 d . . . . .
C2B C 0.5545(4) 0.3463(5) 0.6853(11) 0.091(2) Uani 1 1 d . . . . .
C3B C 0.6021(4) 0.3912(6) 0.6515(13) 0.106(3) Uani 1 1 d . . . . .
C4B C 0.6196(4) 0.3925(6) 0.5234(13) 0.108(3) Uani 1 1 d . . . . .
C5B C 0.6392(4) 0.4683(7) 0.4659(15) 0.114(3) Uani 1 1 d . . . . .
C6B C 0.6209(4) 0.4711(7) 0.3287(12) 0.114(3) Uani 1 1 d . . . . .
C7B C 0.6031(4) 0.5396(7) 0.2758(12) 0.111(3) Uani 1 1 d . . . . .
C8B C 0.5564(6) 0.5373(8) 0.1907(10) 0.123(4) Uani 1 1 d . . . . .
C9B C 0.5293(6) 0.4789(10) 0.1659(8) 0.140(4) Uani 1 1 d . . . . .
C10B C 0.5463(7) 0.4039(8) 0.2188(11) 0.134(3) Uani 1 1 d . . . . .
C11B C 0.5916(5) 0.3990(6) 0.3019(12) 0.115(3) Uani 1 1 d . . . . .
C12B C 0.5899(5) 0.3504(5) 0.4174(15) 0.116(3) Uani 1 1 d . . . . .
C13B C 0.5481(5) 0.3111(4) 0.4505(12) 0.106(3) Uani 1 1 d . . . . .
C14B C 0.500000 0.3153(6) 0.3585(17) 0.117(4) Uani 1 2 d S T P . .
C15B C 0.500000 0.3594(11) 0.2518(19) 0.135(5) Uani 1 2 d S T P . .


_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
C00A C00A 1.434(18) 12_655 ?
C00A C2B 1.411(13) . ?
C00A C13B 1.426(14) . ?
F1A C1A 1.326(6) . ?
I1A C2A 2.085(5) . ?
F2A C3A 1.347(6) . ?
C1A C1A 1.395(11) 7_645 ?
C1A C2A 1.379(7) . ?
C2A C3A 1.366(7) . ?
C3A C3A 1.384(10) 7_645 ?
C1B C1B 1.24(2) 12_655 ?
C1B C2B 1.366(14) . ?
C1B C8B 1.603(16) 4_566 ?
C2B C3B 1.461(14) . ?
C3B C4B 1.376(15) . ?
C3B C7B 1.407(16) 4_566 ?
C4B C5B 1.517(16) . ?
C4B C12B 1.498(19) . ?
C5B C5B 1.30(2) 4_566 ?
C5B C6B 1.471(18) . ?
C6B C7B 1.373(15) . ?
C6B C11B 1.471(17) . ?
C7B C8B 1.454(18) . ?
C8B C9B 1.240(17) . ?
C9B C9B 1.46(3) 12_655 ?
C9B C10B 1.466(18) . ?
C10B C11B 1.415(18) . ?
C10B C15B 1.426(17) . ?
C11B C12B 1.446(17) . ?
C12B C13B 1.290(15) . ?
C13B C14B 1.524(15) . ?
C14B C15B 1.33(3) . ?

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
C2B C00A C00A 117.1(6) . 12_655 ?
C2B C00A C13B 121.4(9) . . ?
C13B C00A C00A 109.7(6) . 12_655 ?
F1A C1A C1A 118.3(3) . 7_645 ?
F1A C1A C2A 121.3(5) . . ?
C2A C1A C1A 120.4(3) . 7_645 ?
C1A C2A I1A 119.7(4) . . ?
C3A C2A I1A 121.7(4) . . ?
C3A C2A C1A 118.7(5) . . ?
F2A C3A C2A 120.6(5) . . ?
F2A C3A C3A 118.5(3) . 7_645 ?
C2A C3A C3A 120.9(3) . 7_645 ?
C1B C1B C2B 122.8(6) 12_655 . ?
C1B C1B C8B 119.4(7) 12_655 4_566 ?
C2B C1B C8B 106.0(10) . 4_566 ?
C00A C2B C3B 116.9(10) . . ?
C1B C2B C00A 120.1(9) . . ?
C1B C2B C3B 110.5(10) . . ?
C4B C3B C2B 119.4(12) . . ?
C4B C3B C7B 118.7(11) . 4_566 ?
C7B C3B C2B 110.0(11) 4_566 . ?
C3B C4B C5B 118.8(12) . . ?
C3B C4B C12B 121.2(11) . . ?
C12B C4B C5B 107.4(11) . . ?
C5B C5B C4B 121.5(17) 4_566 . ?
C5B C5B C6B 118.8(15) 4_566 . ?
C6B C5B C4B 107.2(11) . . ?
C7B C6B C5B 120.1(13) . . ?
C7B C6B C11B 119.7(13) . . ?
C11B C6B C5B 107.6(10) . . ?
C3B C7B C8B 108.8(11) 4_566 . ?
C6B C7B C3B 122.1(13) . 4_566 ?
C6B C7B C8B 118.0(13) . . ?
C7B C8B C1B 104.6(11) . 4_566 ?
C9B C8B C1B 117.6(15) . 4_566 ?
C9B C8B C7B 125.5(15) . . ?
C8B C9B C9B 123.0(11) . 12_655 ?
C8B C9B C10B 119.1(15) . . ?
C9B C9B C10B 106.8(9) 12_655 . ?
C11B C10B C9B 120.2(13) . . ?
C11B C10B C15B 118.2(15) . . ?
C15B C10B C9B 109.2(17) . . ?
C10B C11B C6B 117.3(11) . . ?
C10B C11B C12B 119.9(13) . . ?
C12B C11B C6B 110.8(13) . . ?
C11B C12B C4B 106.9(11) . . ?
C13B C12B C4B 117.9(13) . . ?
C13B C12B C11B 122.8(15) . . ?
C00A C13B C14B 108.3(10) . . ?
C12B C13B C00A 123.2(12) . . ?
C12B C13B C14B 116.8(12) . . ?
C13B C14B C13B 103.8(14) 12_655 . ?
C15B C14B C13B 122.0(8) . 12_655 ?
C15B C14B C13B 122.0(8) . . ?
C10B C15B C10B 108(2) 12_655 . ?
C14B C15B C10B 120.2(11) . 12_655 ?
C14B C15B C10B 120.2(11) . . ?

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
C00A C00A C2B C1B -1.4(8) 12_655 . . . ?
C00A C00A C2B C3B -139.9(6) 12_655 . . . ?
C00A C00A C13B C12B 142.4(8) 12_655 . . . ?
C00A C00A C13B C14B 0.7(7) 12_655 . . . ?
C00A C2B C3B C4B -0.4(11) . . . . ?
C00A C2B C3B C7B 141.9(8) . . . 4_566 ?
C00A C13B C14B C13B -1.0(11) . . . 12_655 ?
C00A C13B C14B C15B 141.9(10) . . . . ?
F1A C1A C2A I1A 1.9(7) . . . . ?
F1A C1A C2A C3A -178.9(5) . . . . ?
I1A C2A C3A F2A -0.1(7) . . . . ?
I1A C2A C3A C3A 179.8(5) . . . 7_645 ?
C1A C1A C2A I1A -177.3(5) 7_645 . . . ?
C1A C1A C2A C3A 1.9(9) 7_645 . . . ?
C1A C2A C3A F2A -179.3(5) . . . . ?
C1A C2A C3A C3A 0.6(10) . . . 7_645 ?
C1B C1B C2B C00A 1.5(9) 12_655 . . . ?
C1B C1B C2B C3B 142.4(5) 12_655 . . . ?
C1B C2B C3B C4B -142.7(9) . . . . ?
C1B C2B C3B C7B -0.4(10) . . . 4_566 ?
C1B C8B C9B C9B -0.9(12) 4_566 . . 12_655 ?
C1B C8B C9B C10B -140.1(11) 4_566 . . . ?
C2B C00A C13B C12B 0.7(12) . . . . ?
C2B C00A C13B C14B -141.1(8) . . . . ?
C2B C3B C4B C5B 139.0(9) . . . . ?
C2B C3B C4B C12B 1.8(13) . . . . ?
C3B C4B C5B C5B -0.8(13) . . . 4_566 ?
C3B C4B C5B C6B -142.0(9) . . . . ?
C3B C4B C12B C11B 141.3(9) . . . . ?
C3B C4B C12B C13B -1.9(13) . . . . ?
C3B C7B C8B C1B -0.6(9) 4_566 . . 4_566 ?
C3B C7B C8B C9B -141.3(12) 4_566 . . . ?
C4B C5B C6B C7B 141.1(9) . . . . ?
C4B C5B C6B C11B -0.7(9) . . . . ?
C4B C12B C13B C00A 0.7(13) . . . . ?
C4B C12B C13B C14B 139.5(9) . . . . ?
C5B C4B C12B C11B -0.1(10) . . . . ?
C5B C4B C12B C13B -143.4(9) . . . . ?
C5B C5B C6B C7B -1.4(13) 4_566 . . . ?
C5B C5B C6B C11B -143.2(8) 4_566 . . . ?
C5B C6B C7B C3B 0.6(14) . . . 4_566 ?
C5B C6B C7B C8B -139.3(11) . . . . ?
C5B C6B C11B C10B 143.4(9) . . . . ?
C5B C6B C11B C12B 0.7(10) . . . . ?
C6B C7B C8B C1B 144.2(8) . . . 4_566 ?
C6B C7B C8B C9B 3.5(16) . . . . ?
C6B C11B C12B C4B -0.4(10) . . . . ?
C6B C11B C12B C13B 140.7(10) . . . . ?
C7B C3B C4B C5B -0.1(13) 4_566 . . . ?
C7B C3B C4B C12B -137.3(10) 4_566 . . . ?
C7B C6B C11B C10B 1.4(13) . . . . ?
C7B C6B C11B C12B -141.3(9) . . . . ?
C7B C8B C9B C9B 135.4(10) . . . 12_655 ?
C7B C8B C9B C10B -3.8(17) . . . . ?
C8B C1B C2B C00A -140.9(7) 4_566 . . . ?
C8B C1B C2B C3B 0.0(9) 4_566 . . . ?
C8B C9B C10B C11B 2.9(16) . . . . ?
C8B C9B C10B C15B 144.4(13) . . . . ?
C9B C9B C10B C11B -142.2(8) 12_655 . . . ?
C9B C9B C10B C15B -0.7(10) 12_655 . . . ?
C9B C10B C11B C6B -1.7(14) . . . . ?
C9B C10B C11B C12B 137.6(11) . . . . ?
C9B C10B C15B C10B 1.2(16) . . . 12_655 ?
C9B C10B C15B C14B -142.0(12) . . . . ?
C10B C11B C12B C4B -142.0(10) . . . . ?
C10B C11B C12B C13B -1.0(15) . . . . ?
C11B C6B C7B C3B 137.9(11) . . . 4_566 ?
C11B C6B C7B C8B -2.1(12) . . . . ?
C11B C10B C15B C10B 143.5(12) . . . 12_655 ?
C11B C10B C15B C14B 0.3(16) . . . . ?
C11B C12B C13B C00A -136.4(11) . . . . ?
C11B C12B C13B C14B 2.4(13) . . . . ?
C12B C4B C5B C5B 141.8(9) . . . 4_566 ?
C12B C4B C5B C6B 0.5(9) . . . . ?
C12B C13B C14B C13B -145.5(8) . . . 12_655 ?
C12B C13B C14B C15B -2.6(14) . . . . ?
C13B C00A C2B C1B 137.7(8) . . . . ?
C13B C00A C2B C3B -0.8(10) . . . . ?
C13B C14B C15B C10B 137.6(8) 12_655 . . . ?
C13B C14B C15B C10B 1.2(16) . . . . ?
C13B C14B C15B C10B -1.2(16) 12_655 . . 12_655 ?
C13B C14B C15B C10B -137.6(8) . . . 12_655 ?
C15B C10B C11B C6B -139.8(10) . . . . ?
C15B C10B C11B C12B -0.5(14) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_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_sfull_a_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2240200'
loop_
_audit_author_name
_audit_author_address
'Jogirdas Vainauskas'
;McGill University, University of Birmingham
Canada
;
_audit_update_record             
;
2023-04-25 deposited with the CCDC.	2023-10-09 downloaded from the CCDC.
;
_audit_creation_date             2022-01-20
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
# start Validation Reply Form
_vrf_PLAT250_sfull_a             
;
PROBLEM: Large U3/U1 Ratio for Average U(i,j) Tensor ....        4.2 Note  
RESPONSE: This is likely due to thermal motion of the pyrene unit.
;
# end Validation Reply Form

_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H10, 2(C6 F4 I2)'
_chemical_formula_sum            'C14 H5 F4 I2'
_chemical_formula_weight         502.98
_chemical_melting_point          ?
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'

_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                   6.1992(3)
_cell_length_b                   9.2122(5)
_cell_length_c                   12.9134(7)
_cell_angle_alpha                107.150(2)
_cell_angle_beta                 94.642(2)
_cell_angle_gamma                97.251(2)
_cell_volume                     693.58(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7546
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      72.42
_cell_measurement_theta_min      3.61
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    35.945
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.2993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1839 before and 0.0831 after correction.
The Ratio of minimum to maximum transmission is 0.1781.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.408
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             462
_exptl_crystal_size_max          0.315
_exptl_crystal_size_mid          0.175
_exptl_crystal_size_min          0.090
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0519
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13339
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.732
_diffrn_reflns_theta_min         3.610
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  
'Bruker D8 Venture, Dual, Cu at zero, PHOTON II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'micro-focus sealed X-ray tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2397
_reflns_number_total             2721
_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       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         1.585
_refine_diff_density_min         -2.428
_refine_diff_density_rms         0.174
_refine_ls_extinction_coef       0.0063(5)
_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   1.131
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2721
_refine_ls_number_restraints     123
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0482
_refine_ls_restrained_S_all      1.108
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0310P)²+5.5506P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1146
_refine_ls_wR_factor_ref         0.1207
_refine_special_details          ?
_olex2_refinement_description    
;
1. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
2.a Aromatic/amide H refined with riding coordinates:
 C3B(H3B), C4B(H4B), C6B(H6B), C7B(H7B), C8B(H8B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
I2A I 0.18611(8) 0.82429(5) 0.35614(4) 0.0441(2) Uani 1 1 d . . . . .
F4A F 0.8487(8) 0.5878(6) 0.5007(6) 0.0698(16) Uani 1 1 d . . . . .
C1A C 0.6556(11) 0.7186(8) 0.6392(7) 0.0388(14) Uani 1 1 d . . . . .
I1A I 0.85831(10) 0.67327(7) 0.75827(6) 0.0703(3) Uani 1 1 d . . . . .
F1A F 0.4490(9) 0.8581(7) 0.7701(4) 0.0616(13) Uani 1 1 d . . . . .
C2A C 0.4862(12) 0.8013(9) 0.6645(6) 0.0391(15) Uani 1 1 d . . . . .
F2A F 0.1931(8) 0.9144(6) 0.6159(4) 0.0551(12) Uani 1 1 d . . . . .
C3A C 0.3551(11) 0.8322(8) 0.5864(6) 0.0361(14) Uani 1 1 d . . . . .
F3A F 0.5977(8) 0.6481(6) 0.3481(4) 0.0578(13) Uani 1 1 d . . . . .
C4A C 0.3862(11) 0.7821(7) 0.4775(6) 0.0320(13) Uani 1 1 d . . . . .
C5A C 0.5566(12) 0.6995(8) 0.4515(6) 0.0384(14) Uani 1 1 d . . . . .
C6A C 0.6919(13) 0.6706(8) 0.5321(7) 0.0420(15) Uani 1 1 d . . . . .
C1B C 1.0180(16) 0.4233(8) -0.0260(5) 0.047(2) Uani 1 1 d . . . . .
C2B C 0.8734(18) 0.2971(10) -0.0158(6) 0.054(2) Uani 1 1 d . . . . .
C3B C 0.7010(19) 0.3287(11) 0.0477(7) 0.063(2) Uani 1 1 d . . . . .
H3B H 0.607441 0.246632 0.055868 0.075 Uiso 1 1 calc R U . . .
C4B C 0.665(2) 0.4748(11) 0.0979(7) 0.067(3) Uani 1 1 d . . . . .
H4B H 0.547491 0.490389 0.138049 0.080 Uiso 1 1 calc R U . . .
C5B C 0.8082(18) 0.6041(10) 0.0887(6) 0.056(2) Uani 1 1 d . . . . .
C6B C 0.774(2) 0.7566(11) 0.1379(7) 0.066(2) Uani 1 1 d . . . . .
H6B H 0.657023 0.774890 0.178355 0.079 Uiso 1 1 calc R U . . .
C7B C 0.913(2) 0.8791(10) 0.1262(7) 0.065(2) Uani 1 1 d . . . . .
H7B H 0.889196 0.979361 0.158089 0.078 Uiso 1 1 calc R U . . .
C8B C 1.0872(19) 0.8523(9) 0.0672(6) 0.058(2) Uani 1 1 d . . . . .
H8B H 1.181372 0.935637 0.061240 0.070 Uiso 1 1 calc R U . . .


_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
I2A C4A 2.076(7) . ?
F4A C6A 1.326(9) . ?
C1A I1A 2.078(7) . ?
C1A C2A 1.378(11) . ?
C1A C6A 1.369(12) . ?
F1A C2A 1.359(9) . ?
C2A C3A 1.362(10) . ?
F2A C3A 1.345(8) . ?
C3A C4A 1.383(10) . ?
F3A C5A 1.336(9) . ?
C4A C5A 1.385(10) . ?
C5A C6A 1.391(11) . ?
C1B C1B 1.429(16) 2_765 ?
C1B C2B 1.421(12) . ?
C1B C5B 1.404(14) 2_765 ?
C2B C3B 1.407(15) . ?
C2B C8B 1.403(13) 2_765 ?
C3B H3B 0.9300 . ?
C3B C4B 1.366(14) . ?
C4B H4B 0.9300 . ?
C4B C5B 1.433(13) . ?
C5B C6B 1.412(13) . ?
C6B H6B 0.9300 . ?
C6B C7B 1.386(16) . ?
C7B H7B 0.9300 . ?
C7B C8B 1.376(16) . ?
C8B H8B 0.9300 . ?

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
C2A C1A I1A 122.0(6) . . ?
C6A C1A I1A 120.3(5) . . ?
C6A C1A C2A 117.6(7) . . ?
F1A C2A C1A 120.2(7) . . ?
F1A C2A C3A 117.9(7) . . ?
C3A C2A C1A 121.9(7) . . ?
C2A C3A C4A 121.4(7) . . ?
F2A C3A C2A 119.4(7) . . ?
F2A C3A C4A 119.3(6) . . ?
C3A C4A I2A 122.3(5) . . ?
C3A C4A C5A 117.1(7) . . ?
C5A C4A I2A 120.6(5) . . ?
F3A C5A C4A 120.5(7) . . ?
F3A C5A C6A 118.3(6) . . ?
C4A C5A C6A 121.1(7) . . ?
F4A C6A C1A 121.3(7) . . ?
F4A C6A C5A 117.7(8) . . ?
C1A C6A C5A 120.8(7) . . ?
C2B C1B C1B 119.5(11) . 2_765 ?
C5B C1B C1B 120.8(10) 2_765 2_765 ?
C5B C1B C2B 119.7(8) 2_765 . ?
C3B C2B C1B 118.2(8) . . ?
C8B C2B C1B 118.4(9) 2_765 . ?
C8B C2B C3B 123.3(8) 2_765 . ?
C2B C3B H3B 118.6 . . ?
C4B C3B C2B 122.8(9) . . ?
C4B C3B H3B 118.6 . . ?
C3B C4B H4B 119.9 . . ?
C3B C4B C5B 120.2(10) . . ?
C5B C4B H4B 119.9 . . ?
C1B C5B C4B 118.6(8) 2_765 . ?
C1B C5B C6B 119.7(9) 2_765 . ?
C6B C5B C4B 121.7(10) . . ?
C5B C6B H6B 119.9 . . ?
C7B C6B C5B 120.3(11) . . ?
C7B C6B H6B 119.9 . . ?
C6B C7B H7B 120.0 . . ?
C8B C7B C6B 119.9(9) . . ?
C8B C7B H7B 120.0 . . ?
C2B C8B H8B 119.1 2_765 . ?
C7B C8B C2B 121.9(9) . 2_765 ?
C7B C8B H8B 119.1 . . ?

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
I2A C4A C5A F3A 1.3(9) . . . . ?
I2A C4A C5A C6A 179.9(5) . . . . ?
C1A C2A C3A F2A -179.5(7) . . . . ?
C1A C2A C3A C4A -0.1(12) . . . . ?
I1A C1A C2A F1A 1.0(10) . . . . ?
I1A C1A C2A C3A 179.3(6) . . . . ?
I1A C1A C6A F4A 3.5(10) . . . . ?
I1A C1A C6A C5A 179.6(5) . . . . ?
F1A C2A C3A F2A -1.2(11) . . . . ?
F1A C2A C3A C4A 178.2(7) . . . . ?
C2A C1A C6A F4A -178.6(7) . . . . ?
C2A C1A C6A C5A -2.5(11) . . . . ?
C2A C3A C4A I2A 179.0(6) . . . . ?
C2A C3A C4A C5A -0.2(11) . . . . ?
F2A C3A C4A I2A -1.6(10) . . . . ?
F2A C3A C4A C5A 179.3(6) . . . . ?
C3A C4A C5A F3A -179.5(6) . . . . ?
C3A C4A C5A C6A -0.9(11) . . . . ?
F3A C5A C6A F4A -2.8(11) . . . . ?
F3A C5A C6A C1A -179.1(7) . . . . ?
C4A C5A C6A F4A 178.5(7) . . . . ?
C4A C5A C6A C1A 2.3(11) . . . . ?
C6A C1A C2A F1A -176.9(7) . . . . ?
C6A C1A C2A C3A 1.4(11) . . . . ?
C1B C1B C2B C3B -1.2(12) 2_765 . . . ?
C1B C1B C2B C8B -179.7(8) 2_765 . . 2_765 ?
C1B C2B C3B C4B 1.2(13) . . . . ?
C1B C5B C6B C7B -1.2(14) 2_765 . . . ?
C2B C3B C4B C5B -1.1(15) . . . . ?
C3B C4B C5B C1B 1.0(14) . . . 2_765 ?
C3B C4B C5B C6B 178.9(9) . . . . ?
C4B C5B C6B C7B -179.0(9) . . . . ?
C5B C1B C2B C3B 180.0(8) 2_765 . . . ?
C5B C1B C2B C8B 1.5(11) 2_765 . . 2_765 ?
C5B C6B C7B C8B -0.6(14) . . . . ?
C6B C7B C8B C2B 1.4(13) . . . 2_765 ?
C8B C2B C3B C4B 179.6(9) 2_765 . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DCM'
####################################################################### 
# 
# 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_2021ncs0398_ljm1a
_database_code_depnum_ccdc_archive 'CCDC 2240207'
loop_
_audit_author_name
_audit_author_address
'Jogirdas Vainauskas'
;McGill University, University of Birmingham
Canada
;
_audit_update_record             
;
2023-04-29 deposited with the CCDC.	2023-10-09 downloaded from the CCDC.
;
_audit_creation_date             2023-04-29
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
# start Validation Reply Form
_vrf_PLAT250_2021ncs0398_ljm1a   
;
PROBLEM: Large U3/U1 Ratio for Average U(i,j) Tensor ....        4.9 Note  
RESPONSE: This is likely due to thermal motion.
;
# end Validation Reply Form
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '3(C6 F4 I2), C48 H20'
_chemical_formula_sum            'C66 H20 F12 I6'
_chemical_formula_weight         1802.22
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C66 H20 I6 F12'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0019 0.0015 '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 0.0124 0.0097 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.7738 1.7195 '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                   5.1812(2)
_cell_length_b                   15.4603(5)
_cell_length_c                   17.4682(6)
_cell_angle_alpha                72.718(3)
_cell_angle_beta                 87.214(3)
_cell_angle_gamma                81.882(3)
_cell_volume                     1322.66(8)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    4702
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      34.6880
_cell_measurement_theta_min      1.5040
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.346
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.35591
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.114a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    2.263
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_description       lath
_exptl_crystal_F_000             842
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0678
_diffrn_reflns_av_unetI/netI     0.0934
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            15312
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        24.415
_diffrn_reflns_theta_max         24.513
_diffrn_reflns_theta_min         1.511
_diffrn_ambient_temperature      100
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  φ      0.00 180.00   0.20    0.20   0.00   0.00   0.00    --   900
  2  ω   -145.00  25.00   0.20    0.20    --   30.00   0.00   0.00  850
  3  ω   -145.00  25.00   0.20    0.20    --   30.00   0.00 120.00  850
  4  ω   -145.00  25.00   0.20    0.20    --   30.00   0.00 240.00  850
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dectris-CrysAlisPro-abstract goniometer imported dectris images'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0229264000
_diffrn_orient_matrix_UB_12      -0.0327513000
_diffrn_orient_matrix_UB_13      0.0364424000
_diffrn_orient_matrix_UB_21      -0.0413199000
_diffrn_orient_matrix_UB_22      0.0323407000
_diffrn_orient_matrix_UB_23      0.0194313000
_diffrn_orient_matrix_UB_31      -0.1257239000
_diffrn_orient_matrix_UB_32      -0.0099153000
_diffrn_orient_matrix_UB_33      0.0005702000
_diffrn_radiation_monochromator  synchrotron
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.6889
_diffrn_source                   synchrotron
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3602
_reflns_number_total             4751
_reflns_odcompleteness_completeness 98.18
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.52
_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 1.171.41.114a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.114a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.114a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.441
_refine_diff_density_min         -1.117
_refine_diff_density_rms         0.134
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     451
_refine_ls_number_reflns         4751
_refine_ls_number_restraints     443
_refine_ls_R_factor_all          0.0843
_refine_ls_R_factor_gt           0.0698
_refine_ls_restrained_S_all      1.008
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0700P)²+4.8563P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1955
_refine_ls_wR_factor_ref         0.2070
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Rigid bond restraints
 F4B, C6B, C1A, I1A, C1A, I2A, C1B, I1B, C1B, I2B
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C4B, I3B, C4B, I4B
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Fixed Sof: C5B(0.7) C6B(0.7) I1A(0.9) F2B(0.7) I2B(0.7) F3B(0.49) I3B(0.7)
 F4B(0.49) C5(0.3) C6(0.3) I2A(0.1) I1B(0.3) I4B(0.3) F5B(0.3) F6B(0.51)
 F7B(0.51)
5.a Aromatic/amide H refined with riding coordinates:
 C4C(H4C), C5C(H5C), C7C(H7C), C8C(H8C), C12C(H12C), C13C(H13C), C15C(H15C),
 C16C(H16C), C20C(H20C), C24C(H24C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
C1A C 1.1799(19) 0.4318(6) 0.5466(6) 0.075(3) Uani 1 1 d . U . . .
F2A F 1.094(2) 0.3351(5) 0.4726(6) 0.151(4) Uani 1 1 d . . . . .
F3A F 0.754(2) 0.4640(5) 0.3839(6) 0.177(5) Uani 1 1 d . . . . .
C2A C 1.046(3) 0.4162(7) 0.4877(8) 0.095(4) Uani 1 1 d . . . . .
C3A C 0.870(3) 0.4848(8) 0.4422(8) 0.107(4) Uani 1 1 d . . . . .
C1B C 1.1076(19) 0.5078(6) 0.1834(7) 0.078(3) Uani 1 1 d . U . . .
C2B C 1.049(2) 0.5970(7) 0.1880(7) 0.091(3) Uani 1 1 d . . . . .
C3B C 0.863(2) 0.6580(7) 0.1403(7) 0.081(3) Uani 1 1 d . . . . .
C4B C 0.7320(19) 0.6345(6) 0.0848(7) 0.081(3) Uani 1 1 d . U . . .
C5B C 0.819(4) 0.5479(12) 0.0728(14) 0.083(5) Uani 0.7 1 d . . P D .
C6B C 0.998(5) 0.4856(15) 0.1223(14) 0.088(6) Uani 0.7 1 d . U P D .
C1C C -0.4696(17) 0.0101(6) 0.7637(5) 0.0630(18) Uani 1 1 d . . . . .
C2C C -0.3166(16) 0.0250(5) 0.6939(5) 0.0577(17) Uani 1 1 d . . . . .
C3C C -0.1479(17) 0.0917(5) 0.6772(5) 0.0609(18) Uani 1 1 d . . . . .
C4C C -0.1379(18) 0.1458(6) 0.7318(6) 0.065(2) Uani 1 1 d . . . . .
H4C H -0.030042 0.191318 0.720673 0.078 Uiso 1 1 calc R U . . .
C5C C -0.2855(18) 0.1296(6) 0.7984(6) 0.068(2) Uani 1 1 d . . . . .
H5C H -0.275125 0.163984 0.833509 0.081 Uiso 1 1 calc R U . . .
C6C C -0.4577(19) 0.0619(6) 0.8177(6) 0.0692(19) Uani 1 1 d . . . . .
C7C C -0.616(2) 0.0420(7) 0.8909(6) 0.076(2) Uani 1 1 d . . . . .
H7C H -0.607482 0.074533 0.927505 0.091 Uiso 1 1 calc R U . . .
C8C C -0.773(2) -0.0234(7) 0.9053(7) 0.082(2) Uani 1 1 d . . . . .
H8C H -0.870239 -0.035357 0.952556 0.098 Uiso 1 1 calc R U . . .
C9C C -0.7956(18) -0.0744(6) 0.8523(6) 0.076(2) Uani 1 1 d . . . . .
C10C C -0.6398(16) -0.0579(5) 0.7815(6) 0.0659(18) Uani 1 1 d . . . . .
C11C C -0.6559(16) -0.1096(6) 0.7269(6) 0.0658(18) Uani 1 1 d . . . . .
C12C C -0.9673(19) -0.1376(7) 0.8654(7) 0.079(2) Uani 1 1 d . . . . .
H12C H -1.074434 -0.146262 0.910610 0.095 Uiso 1 1 calc R U . . .
C13C C -0.9851(17) -0.1877(6) 0.8141(6) 0.075(2) Uani 1 1 d . . . . .
H13C H -1.101661 -0.230531 0.825520 0.090 Uiso 1 1 calc R U . . .
C14C C -0.8296(16) -0.1761(5) 0.7437(6) 0.0689(19) Uani 1 1 d . . . . .
C15C C -0.8438(17) -0.2247(5) 0.6874(6) 0.073(2) Uani 1 1 d . . . . .
H15C H -0.961852 -0.266903 0.696704 0.088 Uiso 1 1 calc R U . . .
C16C C -0.6887(17) -0.2122(5) 0.6185(6) 0.067(2) Uani 1 1 d . . . . .
H16C H -0.700019 -0.246455 0.583379 0.080 Uiso 1 1 calc R U . . .
C17C C -0.5135(15) -0.1466(5) 0.6031(5) 0.0582(17) Uani 1 1 d . . . . .
C18C C -0.4964(15) -0.0948(5) 0.6568(5) 0.0556(16) Uani 1 1 d . . . . .
C19C C -0.3232(14) -0.0279(5) 0.6388(5) 0.0530(15) Uani 1 1 d . . . . .
C20C C -0.3533(15) -0.1295(5) 0.5349(5) 0.0566(17) Uani 1 1 d . . . . .
H20C H -0.365127 -0.162933 0.499134 0.068 Uiso 1 1 calc R U . . .
C21C C -0.1799(15) -0.0668(4) 0.5170(5) 0.0530(17) Uani 1 1 d . . . . .
C22C C -0.1641(14) -0.0143(4) 0.5703(5) 0.0526(16) Uani 1 1 d . . . . .
C23C C 0.0096(15) 0.0543(4) 0.5543(5) 0.0527(17) Uani 1 1 d . . . . .
C24C C 0.0107(16) 0.1060(5) 0.6072(5) 0.0590(18) Uani 1 1 d . . . . .
H24C H 0.118867 0.151460 0.596335 0.071 Uiso 1 1 calc R U . . .
I1A I 1.4391(2) 0.32583(7) 0.61994(7) 0.0859(4) Uani 0.9 1 d . U P A 1
F1B F 1.165(2) 0.6198(6) 0.2431(6) 0.172(5) Uani 1 1 d . . . B 1
F2B F 0.785(6) 0.7381(16) 0.146(2) 0.186(14) Uani 0.7 1 d . . P C 1
I2B I 1.3870(4) 0.40819(11) 0.25109(12) 0.0769(5) Uani 0.7 1 d . U P D 1
F3B F 0.755(4) 0.5214(11) 0.0049(12) 0.111(5) Uani 0.49 1 d . . P D 1
I3B I 0.4651(6) 0.7237(2) 0.0014(2) 0.1147(13) Uani 0.7 1 d . U P E 1
F4B F 1.097(4) 0.4048(12) 0.1005(15) 0.119(7) Uani 0.49 1 d . U P D 1
C5 C 0.728(9) 0.560(3) 0.094(3) 0.079(6) Uani 0.3 1 d . . P D 2
C6 C 0.939(13) 0.488(4) 0.150(4) 0.088(7) Uani 0.3 1 d . . P D 2
I2A I 1.4949(18) 0.3634(5) 0.6195(6) 0.084(3) Uani 0.1 1 d . U P A 2
I1B I 1.3525(13) 0.4310(4) 0.2755(4) 0.133(2) Uani 0.3 1 d . U P D 2
I4B I 0.4581(15) 0.7292(4) 0.0141(5) 0.090(2) Uani 0.3 1 d . U P E 2
F5B F 0.853(8) 0.747(3) 0.149(3) 0.081(7) Uani 0.3 1 d . . P C 2
F6B F 0.601(4) 0.5187(11) 0.0535(11) 0.121(6) Uani 0.51 1 d . . P D 2
F7B F 0.958(4) 0.3994(10) 0.1411(13) 0.119(7) Uani 0.51 1 d . . P D 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
C1A C2A 1.364(14) . ?
C1A C3A 1.347(15) 2_766 ?
C1A I1A 2.104(9) . ?
C1A I2A 2.078(11) . ?
F2A C2A 1.344(12) . ?
F3A C3A 1.348(12) . ?
C2A C3A 1.373(15) . ?
C1B C2B 1.395(14) . ?
C1B C6B 1.38(2) . ?
C1B I2B 2.078(9) . ?
C1B C6 1.19(6) . ?
C1B I1B 2.060(10) . ?
C2B C3B 1.365(14) . ?
C2B F1B 1.317(13) . ?
C3B C4B 1.370(15) . ?
C3B F2B 1.28(2) . ?
C3B F5B 1.42(4) . ?
C4B C5B 1.42(2) . ?
C4B I3B 2.098(9) . ?
C4B C5 1.11(5) . ?
C4B I4B 2.048(11) . ?
C5B C6B 1.36(3) . ?
C5B F3B 1.43(2) . ?
C5B C5 0.63(5) . ?
C6B F4B 1.43(2) . ?
C6B C6 0.57(8) . ?
C1C C2C 1.400(13) . ?
C1C C6C 1.416(13) . ?
C1C C10C 1.421(13) . ?
C2C C3C 1.401(12) . ?
C2C C19C 1.439(11) . ?
C3C C4C 1.450(12) . ?
C3C C24C 1.418(13) . ?
C4C H4C 0.9300 . ?
C4C C5C 1.341(13) . ?
C5C H5C 0.9300 . ?
C5C C6C 1.425(14) . ?
C6C C7C 1.461(15) . ?
C7C H7C 0.9300 . ?
C7C C8C 1.345(16) . ?
C8C H8C 0.9300 . ?
C8C C9C 1.402(16) . ?
C9C C10C 1.421(14) . ?
C9C C12C 1.375(15) . ?
C10C C11C 1.425(13) . ?
C11C C14C 1.417(13) . ?
C11C C18C 1.423(13) . ?
C12C H12C 0.9300 . ?
C12C C13C 1.362(15) . ?
C13C H13C 0.9300 . ?
C13C C14C 1.417(14) . ?
C14C C15C 1.415(14) . ?
C15C H15C 0.9300 . ?
C15C C16C 1.394(14) . ?
C16C H16C 0.9300 . ?
C16C C17C 1.415(12) . ?
C17C C18C 1.416(12) . ?
C17C C20C 1.399(12) . ?
C18C C19C 1.420(11) . ?
C19C C22C 1.401(12) . ?
C20C H20C 0.9300 . ?
C20C C21C 1.372(11) . ?
C21C C22C 1.416(11) . ?
C21C C23C 1.472(12) 2_556 ?
C22C C23C 1.442(11) . ?
C23C C24C 1.391(11) . ?
C24C H24C 0.9300 . ?
C5 C6 1.59(6) . ?
C5 F6B 1.33(4) . ?
C6 F7B 1.42(5) . ?

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
C2A C1A I1A 120.1(7) . . ?
C2A C1A I2A 135.7(8) . . ?
C3A C1A C2A 117.6(9) 2_766 . ?
C3A C1A I1A 122.3(7) 2_766 . ?
C3A C1A I2A 106.2(7) 2_766 . ?
C1A C2A C3A 119.6(9) . . ?
F2A C2A C1A 120.0(9) . . ?
F2A C2A C3A 120.3(10) . . ?
C1A C3A F3A 121.8(10) 2_766 . ?
C1A C3A C2A 122.9(10) 2_766 . ?
F3A C3A C2A 115.4(10) . . ?
C2B C1B I2B 125.5(7) . . ?
C2B C1B I1B 110.0(8) . . ?
C6B C1B C2B 118.2(11) . . ?
C6B C1B I2B 115.7(10) . . ?
C6B C1B I1B 131.8(10) . . ?
C6 C1B C2B 111(2) . . ?
C6 C1B C6B 24(4) . . ?
C6 C1B I1B 132(3) . . ?
C3B C2B C1B 121.3(10) . . ?
F1B C2B C1B 118.4(9) . . ?
F1B C2B C3B 120.2(10) . . ?
C2B C3B C4B 121.2(9) . . ?
C2B C3B F5B 112(2) . . ?
C4B C3B F5B 126(2) . . ?
F2B C3B C2B 124.4(15) . . ?
F2B C3B C4B 114.3(14) . . ?
C3B C4B C5B 116.8(10) . . ?
C3B C4B I3B 125.4(7) . . ?
C3B C4B I4B 119.5(7) . . ?
C5B C4B I3B 116.7(10) . . ?
C5B C4B I4B 123.2(10) . . ?
C5 C4B C3B 117(2) . . ?
C5 C4B C5B 25(3) . . ?
C5 C4B I4B 120(2) . . ?
C4B C5B F3B 124.5(15) . . ?
C6B C5B C4B 121.5(17) . . ?
C6B C5B F3B 113.6(15) . . ?
C5 C5B C4B 48(6) . . ?
C5 C5B C6B 109(6) . . ?
C1B C6B F4B 121.6(18) . . ?
C5B C6B C1B 120.0(16) . . ?
C5B C6B F4B 117.6(18) . . ?
C6 C6B C1B 59(8) . . ?
C6 C6B C5B 92(7) . . ?
C2C C1C C6C 120.9(9) . . ?
C2C C1C C10C 120.2(8) . . ?
C6C C1C C10C 118.9(9) . . ?
C1C C2C C3C 119.8(8) . . ?
C1C C2C C19C 121.7(8) . . ?
C3C C2C C19C 118.5(8) . . ?
C2C C3C C4C 119.4(9) . . ?
C2C C3C C24C 120.0(8) . . ?
C24C C3C C4C 120.6(8) . . ?
C3C C4C H4C 120.3 . . ?
C5C C4C C3C 119.5(9) . . ?
C5C C4C H4C 120.3 . . ?
C4C C5C H5C 118.7 . . ?
C4C C5C C6C 122.6(9) . . ?
C6C C5C H5C 118.7 . . ?
C1C C6C C5C 117.8(9) . . ?
C1C C6C C7C 118.8(10) . . ?
C5C C6C C7C 123.4(9) . . ?
C6C C7C H7C 120.0 . . ?
C8C C7C C6C 120.1(10) . . ?
C8C C7C H7C 120.0 . . ?
C7C C8C H8C 118.6 . . ?
C7C C8C C9C 122.8(11) . . ?
C9C C8C H8C 118.6 . . ?
C8C C9C C10C 118.4(10) . . ?
C12C C9C C8C 122.4(11) . . ?
C12C C9C C10C 119.3(11) . . ?
C1C C10C C11C 119.3(9) . . ?
C9C C10C C1C 121.0(9) . . ?
C9C C10C C11C 119.7(9) . . ?
C14C C11C C10C 119.4(9) . . ?
C14C C11C C18C 120.6(9) . . ?
C18C C11C C10C 120.0(8) . . ?
C9C C12C H12C 119.1 . . ?
C13C C12C C9C 121.9(10) . . ?
C13C C12C H12C 119.1 . . ?
C12C C13C H13C 119.3 . . ?
C12C C13C C14C 121.3(9) . . ?
C14C C13C H13C 119.3 . . ?
C13C C14C C11C 118.3(10) . . ?
C15C C14C C11C 117.8(9) . . ?
C15C C14C C13C 123.8(9) . . ?
C14C C15C H15C 118.6 . . ?
C16C C15C C14C 122.8(8) . . ?
C16C C15C H15C 118.6 . . ?
C15C C16C H16C 120.6 . . ?
C15C C16C C17C 118.8(9) . . ?
C17C C16C H16C 120.6 . . ?
C16C C17C C18C 120.4(9) . . ?
C20C C17C C16C 122.1(8) . . ?
C20C C17C C18C 117.4(7) . . ?
C17C C18C C11C 119.5(8) . . ?
C17C C18C C19C 119.2(8) . . ?
C19C C18C C11C 121.2(8) . . ?
C18C C19C C2C 117.5(8) . . ?
C22C C19C C2C 121.4(7) . . ?
C22C C19C C18C 121.1(7) . . ?
C17C C20C H20C 117.7 . . ?
C21C C20C C17C 124.5(8) . . ?
C21C C20C H20C 117.7 . . ?
C20C C21C C22C 118.2(8) . . ?
C20C C21C C23C 122.0(7) . 2_556 ?
C22C C21C C23C 119.8(7) . 2_556 ?
C19C C22C C21C 119.5(7) . . ?
C19C C22C C23C 119.4(7) . . ?
C21C C22C C23C 121.1(8) . . ?
C22C C23C C21C 119.0(7) . 2_556 ?
C24C C23C C21C 122.3(7) . 2_556 ?
C24C C23C C22C 118.7(8) . . ?
C3C C24C H24C 119.0 . . ?
C23C C24C C3C 122.1(8) . . ?
C23C C24C H24C 119.0 . . ?
C4B C5 C6 119(4) . . ?
C4B C5 F6B 130(4) . . ?
C5B C5 C4B 107(8) . . ?
C5B C5 C6 70(5) . . ?
C5B C5 F6B 80(5) . . ?
F6B C5 C6 110(4) . . ?
C1B C6 C5 124(4) . . ?
C1B C6 F7B 120(4) . . ?
C6B C6 C1B 97(10) . . ?
C6B C6 C5 89(7) . . ?
C6B C6 F7B 68(7) . . ?
F7B C6 C5 114(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1A C2A C3A C1A -1(3) . . . 2_766 ?
C1A C2A C3A F3A 178.1(14) . . . . ?
F2A C2A C3A C1A -178.3(14) . . . 2_766 ?
F2A C2A C3A F3A 0(2) . . . . ?
C3A C1A C2A F2A 178.3(14) 2_766 . . . ?
C3A C1A C2A C3A 1(2) 2_766 . . . ?
C1B C2B C3B C4B -2(2) . . . . ?
C1B C2B C3B F2B 174(2) . . . . ?
C1B C2B C3B F5B -174(2) . . . . ?
C1B C6B C6 C5 125(5) . . . . ?
C1B C6B C6 F7B -119(3) . . . . ?
C2B C1B C6B C5B -6(3) . . . . ?
C2B C1B C6B F4B 163.7(19) . . . . ?
C2B C1B C6B C6 -78(8) . . . . ?
C2B C1B C6 C6B 113(7) . . . . ?
C2B C1B C6 C5 19(7) . . . . ?
C2B C1B C6 F7B -178(4) . . . . ?
C2B C3B C4B C5B -7(2) . . . . ?
C2B C3B C4B I3B -174.7(10) . . . . ?
C2B C3B C4B C5 21(4) . . . . ?
C2B C3B C4B I4B -179.4(10) . . . . ?
C3B C4B C5B C6B 10(3) . . . . ?
C3B C4B C5B F3B -163.1(18) . . . . ?
C3B C4B C5B C5 98(6) . . . . ?
C3B C4B C5 C5B -95(7) . . . . ?
C3B C4B C5 C6 -19(6) . . . . ?
C3B C4B C5 F6B 174(4) . . . . ?
C4B C5B C6B C1B -3(4) . . . . ?
C4B C5B C6B F4B -173(2) . . . . ?
C4B C5B C6B C6 51(9) . . . . ?
C4B C5B C5 C6 -115(5) . . . . ?
C4B C5B C5 F6B 129(5) . . . . ?
C4B C5 C6 C1B -1(9) . . . . ?
C4B C5 C6 C6B -99(9) . . . . ?
C4B C5 C6 F7B -165(5) . . . . ?
C5B C4B C5 C6 76(6) . . . . ?
C5B C4B C5 F6B -91(9) . . . . ?
C5B C6B C6 C1B -124(3) . . . . ?
C5B C6B C6 C5 0(4) . . . . ?
C5B C6B C6 F7B 116(2) . . . . ?
C5B C5 C6 C1B 97(8) . . . . ?
C5B C5 C6 C6B -1(9) . . . . ?
C5B C5 C6 F7B -66(7) . . . . ?
C6B C1B C2B C3B 8(2) . . . . ?
C6B C1B C2B F1B -176.0(18) . . . . ?
C6B C1B C6 C5 -94(10) . . . . ?
C6B C1B C6 F7B 69(7) . . . . ?
C6B C5B C5 C4B 116(4) . . . . ?
C6B C5B C5 C6 0(4) . . . . ?
C6B C5B C5 F6B -115(3) . . . . ?
C1C C2C C3C C4C -1.2(11) . . . . ?
C1C C2C C3C C24C 178.9(7) . . . . ?
C1C C2C C19C C18C 1.6(10) . . . . ?
C1C C2C C19C C22C -178.2(6) . . . . ?
C1C C6C C7C C8C -1.3(12) . . . . ?
C1C C10C C11C C14C -178.7(6) . . . . ?
C1C C10C C11C C18C 2.0(10) . . . . ?
C2C C1C C6C C5C 0.1(11) . . . . ?
C2C C1C C6C C7C -178.3(7) . . . . ?
C2C C1C C10C C9C 179.7(7) . . . . ?
C2C C1C C10C C11C -1.0(10) . . . . ?
C2C C3C C4C C5C 1.6(11) . . . . ?
C2C C3C C24C C23C -1.4(11) . . . . ?
C2C C19C C22C C21C -179.0(6) . . . . ?
C2C C19C C22C C23C -0.1(9) . . . . ?
C3C C2C C19C C18C -179.7(6) . . . . ?
C3C C2C C19C C22C 0.5(10) . . . . ?
C3C C4C C5C C6C -1.2(12) . . . . ?
C4C C3C C24C C23C 178.8(7) . . . . ?
C4C C5C C6C C1C 0.3(12) . . . . ?
C4C C5C C6C C7C 178.6(8) . . . . ?
C5C C6C C7C C8C -179.5(8) . . . . ?
C6C C1C C2C C3C 0.4(11) . . . . ?
C6C C1C C2C C19C 179.1(7) . . . . ?
C6C C1C C10C C9C -0.2(11) . . . . ?
C6C C1C C10C C11C 179.1(7) . . . . ?
C6C C7C C8C C9C -0.6(13) . . . . ?
C7C C8C C9C C10C 2.0(13) . . . . ?
C7C C8C C9C C12C -176.3(8) . . . . ?
C8C C9C C10C C1C -1.5(11) . . . . ?
C8C C9C C10C C11C 179.1(7) . . . . ?
C8C C9C C12C C13C -179.0(8) . . . . ?
C9C C10C C11C C14C 0.7(10) . . . . ?
C9C C10C C11C C18C -178.7(6) . . . . ?
C9C C12C C13C C14C -1.1(13) . . . . ?
C10C C1C C2C C3C -179.5(7) . . . . ?
C10C C1C C2C C19C -0.8(11) . . . . ?
C10C C1C C6C C5C 180.0(7) . . . . ?
C10C C1C C6C C7C 1.6(11) . . . . ?
C10C C9C C12C C13C 2.8(13) . . . . ?
C10C C11C C14C C13C 1.0(10) . . . . ?
C10C C11C C14C C15C 178.8(7) . . . . ?
C10C C11C C18C C17C 179.9(6) . . . . ?
C10C C11C C18C C19C -1.2(10) . . . . ?
C11C C14C C15C C16C 2.4(12) . . . . ?
C11C C18C C19C C2C -0.6(9) . . . . ?
C11C C18C C19C C22C 179.2(6) . . . . ?
C12C C9C C10C C1C 176.8(7) . . . . ?
C12C C9C C10C C11C -2.6(11) . . . . ?
C12C C13C C14C C11C -0.9(11) . . . . ?
C12C C13C C14C C15C -178.5(8) . . . . ?
C13C C14C C15C C16C -179.9(7) . . . . ?
C14C C11C C18C C17C 0.5(10) . . . . ?
C14C C11C C18C C19C 179.4(6) . . . . ?
C14C C15C C16C C17C -1.6(12) . . . . ?
C15C C16C C17C C18C 0.1(11) . . . . ?
C15C C16C C17C C20C -179.4(7) . . . . ?
C16C C17C C18C C11C 0.3(10) . . . . ?
C16C C17C C18C C19C -178.6(6) . . . . ?
C16C C17C C20C C21C -179.9(7) . . . . ?
C17C C18C C19C C2C 178.4(6) . . . . ?
C17C C18C C19C C22C -1.9(10) . . . . ?
C17C C20C C21C C22C -1.2(10) . . . . ?
C17C C20C C21C C23C 177.8(6) . . . 2_556 ?
C18C C11C C14C C13C -179.7(7) . . . . ?
C18C C11C C14C C15C -1.8(11) . . . . ?
C18C C17C C20C C21C 0.6(10) . . . . ?
C18C C19C C22C C21C 1.3(10) . . . . ?
C18C C19C C22C C23C -179.9(6) . . . . ?
C19C C2C C3C C4C -180.0(6) . . . . ?
C19C C2C C3C C24C 0.2(10) . . . . ?
C19C C22C C23C C21C 178.8(6) . . . 2_556 ?
C19C C22C C23C C24C -1.0(9) . . . . ?
C20C C17C C18C C11C 179.9(6) . . . . ?
C20C C17C C18C C19C 0.9(9) . . . . ?
C20C C21C C22C C19C 0.3(9) . . . . ?
C20C C21C C22C C23C -178.6(6) . . . . ?
C21C C22C C23C C21C -2.4(10) . . . 2_556 ?
C21C C22C C23C C24C 177.8(6) . . . . ?
C21C C23C C24C C3C -178.0(6) 2_556 . . . ?
C22C C23C C24C C3C 1.8(10) . . . . ?
C23C C21C C22C C19C -178.8(6) 2_556 . . . ?
C23C C21C C22C C23C 2.4(10) 2_556 . . . ?
C24C C3C C4C C5C -178.5(7) . . . . ?
I1A C1A C2A F2A -4.8(19) . . . . ?
I1A C1A C2A C3A 177.5(11) . . . . ?
F1B C2B C3B C4B -177.3(13) . . . . ?
F1B C2B C3B F2B -2(3) . . . . ?
F2B C3B C4B C5B 177(2) . . . . ?
F2B C3B C4B I3B 9(2) . . . . ?
I2B C1B C2B C3B 179.3(10) . . . . ?
I2B C1B C2B F1B -4.8(19) . . . . ?
I2B C1B C6B C5B -177.6(18) . . . . ?
I2B C1B C6B F4B -8(3) . . . . ?
F3B C5B C6B C1B 170(2) . . . . ?
F3B C5B C6B F4B 1(3) . . . . ?
I3B C4B C5B C6B 178.3(18) . . . . ?
I3B C4B C5B F3B 6(3) . . . . ?
C5 C4B C5B C6B -88(7) . . . . ?
C5 C5B C6B C1B -55(7) . . . . ?
C5 C5B C6B C6 -1(11) . . . . ?
C6 C1B C2B C3B -17(4) . . . . ?
C6 C1B C6B C5B 72(7) . . . . ?
I2A C1A C2A F2A 9(2) . . . . ?
I2A C1A C2A C3A -169.2(12) . . . . ?
I1B C1B C2B C3B -171.2(11) . . . . ?
I1B C1B C6B C5B 173.6(16) . . . . ?
I1B C1B C6B C6 101(7) . . . . ?
I1B C1B C6 C6B -101(8) . . . . ?
I1B C1B C6 C5 166(3) . . . . ?
I1B C1B C6 F7B -32(8) . . . . ?
I4B C4B C5B C6B -178.4(18) . . . . ?
I4B C4B C5B C5 -90(7) . . . . ?
I4B C4B C5 C5B 105(6) . . . . ?
I4B C4B C5 C6 -179(4) . . . . ?
I4B C4B C5 F6B 14(8) . . . . ?
F5B C3B C4B C5B 164(3) . . . . ?
F5B C3B C4B C5 -168(4) . . . . ?
F5B C3B C4B I4B -8(3) . . . . ?
F6B C5 C6 C1B 168(6) . . . . ?
F6B C5 C6 C6B 70(10) . . . . ?
F6B C5 C6 F7B 4(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 2.069
_oxdiff_exptl_absorpt_empirical_full_min 0.409
_exptl_crystal_recrystallization_method 'From the Melt'
####################################################################### 
# 
# 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_s3_a
_database_code_depnum_ccdc_archive 'CCDC 2240206'
loop_
_audit_author_name
_audit_author_address
'Jogirdas Vainauskas'
;McGill University, University of Birmingham
Canada
;
_audit_update_record             
;
2023-04-25 deposited with the CCDC.	2023-10-09 downloaded from the CCDC.
;
_audit_creation_date             2022-01-20
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 F8 I2 N2, 0.5(C16 H10)'
_chemical_formula_sum            'C20 H5 F8 I2 N2'
_chemical_formula_weight         679.06
_chemical_melting_point          ?
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'

_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                   6.04030(10)
_cell_length_b                   12.6794(3)
_cell_length_c                   13.4013(4)
_cell_angle_alpha                88.433(2)
_cell_angle_beta                 79.590(2)
_cell_angle_gamma                84.594(2)
_cell_volume                     1004.93(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6616
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      72.40
_cell_measurement_theta_min      3.35
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    25.381
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.4835
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1839 before and 0.0831 after correction.
The Ratio of minimum to maximum transmission is 0.1781.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    2.244
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             634
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0502
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16872
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.458
_diffrn_reflns_theta_min         3.353
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  
'Bruker D8 Venture, Dual, Cu at zero, PHOTON II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'micro-focus sealed X-ray tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3014
_reflns_number_total             3937
_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       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         1.227
_refine_diff_density_min         -1.309
_refine_diff_density_rms         0.112
_refine_ls_extinction_coef       0.0023(5)
_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   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         3937
_refine_ls_number_restraints     234
_refine_ls_R_factor_all          0.0656
_refine_ls_R_factor_gt           0.0492
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0976P)²+1.3311P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1466
_refine_ls_wR_factor_ref         0.1699
_refine_special_details          ?
_olex2_refinement_description    
;
1. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
2.a Aromatic/amide H refined with riding coordinates:
 C3B(H3B), C4B(H4B), C5B(H5B), C7B(H7B), C8B(H8B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
I1A I -0.24851(8) 0.69748(4) 0.90983(5) 0.0846(3) Uani 1 1 d . . . . .
I2A I 1.28719(9) 0.04226(4) 0.34433(4) 0.0724(3) Uani 1 1 d . . . . .
N1A N 0.5571(13) 0.3926(5) 0.6667(5) 0.0703(15) Uani 1 1 d . . . . .
F1A F 0.2042(8) 0.5784(4) 0.9619(3) 0.0736(12) Uani 1 1 d . . . . .
N2A N 0.5334(13) 0.3641(6) 0.5883(6) 0.0796(18) Uani 1 1 d . . . . .
F2A F 0.5331(8) 0.4543(4) 0.8534(4) 0.0739(12) Uani 1 1 d . . . . .
F3A F 0.1454(11) 0.4823(4) 0.5764(4) 0.0895(15) Uani 1 1 d . . . . .
F4A F -0.1806(9) 0.6081(4) 0.6846(5) 0.0893(15) Uani 1 1 d . . . . .
F5A F 0.9598(9) 0.2794(4) 0.6712(3) 0.0786(12) Uani 1 1 d . . . . .
F6A F 1.2601(8) 0.1430(4) 0.5625(3) 0.0766(13) Uani 1 1 d . . . . .
F7A F 0.8299(9) 0.1638(5) 0.3012(4) 0.0838(14) Uani 1 1 d . . . . .
F8A F 0.5237(8) 0.2971(5) 0.4095(4) 0.0905(16) Uani 1 1 d . . . . .
C1A C 0.0049(10) 0.5971(5) 0.8253(5) 0.0494(13) Uani 1 1 d . . . . .
C2A C 0.1892(11) 0.5569(5) 0.8639(5) 0.0494(13) Uani 1 1 d . . . . .
C3A C 0.3573(11) 0.4914(5) 0.8097(5) 0.0506(13) Uani 1 1 d . . . . .
C4A C 0.3521(12) 0.4631(5) 0.7114(5) 0.0569(14) Uani 1 1 d . . . . .
C5A C 0.1627(14) 0.5042(5) 0.6716(5) 0.0606(15) Uani 1 1 d . . . . .
C6A C -0.0072(13) 0.5702(5) 0.7279(6) 0.0602(15) Uani 1 1 d . . . . .
C7A C 0.7269(12) 0.2934(5) 0.5438(6) 0.0596(15) Uani 1 1 d . . . . .
C8A C 0.9231(12) 0.2515(5) 0.5803(5) 0.0563(14) Uani 1 1 d . . . . .
C9A C 1.0793(11) 0.1810(5) 0.5234(5) 0.0526(14) Uani 1 1 d . . . . .
C10A C 1.0527(10) 0.1482(5) 0.4305(5) 0.0486(13) Uani 1 1 d . . . . .
C11A C 0.8637(11) 0.1899(6) 0.3921(5) 0.0566(15) Uani 1 1 d . . . . .
C12A C 0.7021(12) 0.2618(6) 0.4489(6) 0.0606(15) Uani 1 1 d . . . . .
C1B C 0.4754(10) 0.0308(4) -0.0417(4) 0.0437(11) Uani 1 1 d . . . . .
C2B C 0.3138(11) 0.0083(5) -0.0983(5) 0.0536(14) Uani 1 1 d . . . . .
C3B C 0.2710(14) 0.0753(6) -0.1796(5) 0.0661(17) Uani 1 1 d . . . . .
H3B H 0.162731 0.059891 -0.217037 0.079 Uiso 1 1 calc R U . . .
C4B C 0.3848(15) 0.1612(6) -0.2038(6) 0.0695(18) Uani 1 1 d . . . . .
H4B H 0.351995 0.205001 -0.256971 0.083 Uiso 1 1 calc R U . . .
C5B C 0.5517(14) 0.1861(6) -0.1504(6) 0.0655(16) Uani 1 1 d . . . . .
H5B H 0.631532 0.244717 -0.169785 0.079 Uiso 1 1 calc R U . . .
C6B C 0.5987(11) 0.1235(5) -0.0687(5) 0.0508(13) Uani 1 1 d . . . . .
C7B C 0.7620(12) 0.1458(5) -0.0104(6) 0.0586(15) Uani 1 1 d . . . . .
H7B H 0.842401 0.204776 -0.027163 0.070 Uiso 1 1 calc R U . . .
C8B C 0.8049(13) 0.0828(6) 0.0699(6) 0.0645(17) Uani 1 1 d . . . . .
H8B H 0.913243 0.099874 0.106567 0.077 Uiso 1 1 calc R U . . .


_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
I1A C1A 2.081(6) . ?
I2A C10A 2.068(6) . ?
N1A N2A 1.157(10) . ?
N1A C4A 1.498(10) . ?
F1A C2A 1.369(8) . ?
N2A C7A 1.450(10) . ?
F2A C3A 1.344(8) . ?
F3A C5A 1.338(8) . ?
F4A C6A 1.332(8) . ?
F5A C8A 1.340(8) . ?
F6A C9A 1.339(8) . ?
F7A C11A 1.326(8) . ?
F8A C12A 1.320(8) . ?
C1A C2A 1.361(9) . ?
C1A C6A 1.373(10) . ?
C2A C3A 1.362(9) . ?
C3A C4A 1.382(10) . ?
C4A C5A 1.399(11) . ?
C5A C6A 1.384(11) . ?
C7A C8A 1.414(10) . ?
C7A C12A 1.382(11) . ?
C8A C9A 1.375(9) . ?
C9A C10A 1.365(9) . ?
C10A C11A 1.390(9) . ?
C11A C12A 1.402(10) . ?
C1B C1B 1.405(12) 2_655 ?
C1B C2B 1.393(9) . ?
C1B C6B 1.453(9) . ?
C2B C3B 1.410(10) . ?
C2B C8B 1.423(10) 2_655 ?
C3B H3B 0.9300 . ?
C3B C4B 1.343(12) . ?
C4B H4B 0.9300 . ?
C4B C5B 1.400(12) . ?
C5B H5B 0.9300 . ?
C5B C6B 1.390(10) . ?
C6B C7B 1.416(10) . ?
C7B H7B 0.9300 . ?
C7B C8B 1.371(11) . ?
C8B H8B 0.9300 . ?

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
N2A N1A C4A 108.8(7) . . ?
N1A N2A C7A 110.2(8) . . ?
C2A C1A I1A 121.3(5) . . ?
C2A C1A C6A 117.8(6) . . ?
C6A C1A I1A 120.9(5) . . ?
C1A C2A F1A 119.7(6) . . ?
C1A C2A C3A 122.2(6) . . ?
C3A C2A F1A 118.0(6) . . ?
F2A C3A C2A 118.8(6) . . ?
F2A C3A C4A 119.5(6) . . ?
C2A C3A C4A 121.7(6) . . ?
C3A C4A N1A 112.1(6) . . ?
C3A C4A C5A 116.1(6) . . ?
C5A C4A N1A 131.8(7) . . ?
F3A C5A C4A 120.1(7) . . ?
F3A C5A C6A 118.4(7) . . ?
C4A C5A C6A 121.4(7) . . ?
F4A C6A C1A 121.0(7) . . ?
F4A C6A C5A 118.2(7) . . ?
C1A C6A C5A 120.7(7) . . ?
C8A C7A N2A 132.4(7) . . ?
C12A C7A N2A 110.3(7) . . ?
C12A C7A C8A 117.3(6) . . ?
F5A C8A C7A 120.7(6) . . ?
F5A C8A C9A 118.6(6) . . ?
C9A C8A C7A 120.7(6) . . ?
F6A C9A C8A 118.0(6) . . ?
F6A C9A C10A 120.0(6) . . ?
C10A C9A C8A 122.0(6) . . ?
C9A C10A I2A 122.2(5) . . ?
C9A C10A C11A 118.4(6) . . ?
C11A C10A I2A 119.4(5) . . ?
F7A C11A C10A 121.6(6) . . ?
F7A C11A C12A 117.8(6) . . ?
C10A C11A C12A 120.5(6) . . ?
F8A C12A C7A 121.1(7) . . ?
F8A C12A C11A 117.8(7) . . ?
C7A C12A C11A 121.1(6) . . ?
C1B C1B C6B 117.7(7) 2_655 . ?
C2B C1B C1B 123.5(7) . 2_655 ?
C2B C1B C6B 118.8(6) . . ?
C3B C2B C1B 120.1(7) . . ?
C3B C2B C8B 122.3(7) . 2_655 ?
C8B C2B C1B 117.6(6) 2_655 . ?
C2B C3B H3B 119.6 . . ?
C4B C3B C2B 120.8(8) . . ?
C4B C3B H3B 119.6 . . ?
C3B C4B H4B 119.3 . . ?
C3B C4B C5B 121.3(7) . . ?
C5B C4B H4B 119.3 . . ?
C4B C5B H5B 119.8 . . ?
C6B C5B C4B 120.3(7) . . ?
C6B C5B H5B 119.8 . . ?
C5B C6B C1B 118.7(6) . . ?
C5B C6B C7B 123.0(6) . . ?
C7B C6B C1B 118.3(6) . . ?
C6B C7B H7B 119.1 . . ?
C8B C7B C6B 121.8(6) . . ?
C8B C7B H7B 119.1 . . ?
C2B C8B H8B 119.5 2_655 . ?
C7B C8B C2B 121.1(7) . 2_655 ?
C7B C8B H8B 119.5 . . ?

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
I1A C1A C2A F1A 3.3(8) . . . . ?
I1A C1A C2A C3A -179.8(5) . . . . ?
I1A C1A C6A F4A 0.4(9) . . . . ?
I1A C1A C6A C5A 179.4(5) . . . . ?
I2A C10A C11A F7A -0.2(9) . . . . ?
I2A C10A C11A C12A 180.0(5) . . . . ?
N1A N2A C7A C8A 3.6(13) . . . . ?
N1A N2A C7A C12A -178.2(7) . . . . ?
N1A C4A C5A F3A -0.7(12) . . . . ?
N1A C4A C5A C6A -179.0(7) . . . . ?
F1A C2A C3A F2A -2.5(9) . . . . ?
F1A C2A C3A C4A 178.1(6) . . . . ?
N2A N1A C4A C3A 173.7(7) . . . . ?
N2A N1A C4A C5A -6.7(12) . . . . ?
N2A C7A C8A F5A -2.6(12) . . . . ?
N2A C7A C8A C9A 177.1(8) . . . . ?
N2A C7A C12A F8A 1.3(10) . . . . ?
N2A C7A C12A C11A -177.6(7) . . . . ?
F2A C3A C4A N1A -0.8(9) . . . . ?
F2A C3A C4A C5A 179.5(6) . . . . ?
F3A C5A C6A F4A 0.4(10) . . . . ?
F3A C5A C6A C1A -178.6(6) . . . . ?
F5A C8A C9A F6A 0.6(10) . . . . ?
F5A C8A C9A C10A 179.5(6) . . . . ?
F6A C9A C10A I2A -1.2(9) . . . . ?
F6A C9A C10A C11A -179.6(6) . . . . ?
F7A C11A C12A F8A 1.6(10) . . . . ?
F7A C11A C12A C7A -179.5(7) . . . . ?
C1A C2A C3A F2A -179.5(6) . . . . ?
C1A C2A C3A C4A 1.0(10) . . . . ?
C2A C1A C6A F4A -178.8(6) . . . . ?
C2A C1A C6A C5A 0.2(10) . . . . ?
C2A C3A C4A N1A 178.7(6) . . . . ?
C2A C3A C4A C5A -1.0(10) . . . . ?
C3A C4A C5A F3A 178.9(6) . . . . ?
C3A C4A C5A C6A 0.6(10) . . . . ?
C4A N1A N2A C7A -178.6(6) . . . . ?
C4A C5A C6A F4A 178.8(6) . . . . ?
C4A C5A C6A C1A -0.2(11) . . . . ?
C6A C1A C2A F1A -177.6(6) . . . . ?
C6A C1A C2A C3A -0.6(9) . . . . ?
C7A C8A C9A F6A -179.1(6) . . . . ?
C7A C8A C9A C10A -0.2(11) . . . . ?
C8A C7A C12A F8A 179.9(7) . . . . ?
C8A C7A C12A C11A 1.0(10) . . . . ?
C8A C9A C10A I2A 179.9(5) . . . . ?
C8A C9A C10A C11A 1.5(10) . . . . ?
C9A C10A C11A F7A 178.2(6) . . . . ?
C9A C10A C11A C12A -1.6(10) . . . . ?
C10A C11A C12A F8A -178.6(7) . . . . ?
C10A C11A C12A C7A 0.3(11) . . . . ?
C12A C7A C8A F5A 179.3(6) . . . . ?
C12A C7A C8A C9A -1.1(10) . . . . ?
C1B C1B C2B C3B 178.7(7) 2_655 . . . ?
C1B C1B C2B C8B -0.7(10) 2_655 . . 2_655 ?
C1B C1B C6B C5B -179.6(6) 2_655 . . . ?
C1B C1B C6B C7B 0.6(9) 2_655 . . . ?
C1B C2B C3B C4B 0.1(10) . . . . ?
C1B C6B C7B C8B -0.2(10) . . . . ?
C2B C1B C6B C5B -0.3(8) . . . . ?
C2B C1B C6B C7B 179.8(6) . . . . ?
C2B C3B C4B C5B 1.1(12) . . . . ?
C3B C4B C5B C6B -2.0(11) . . . . ?
C4B C5B C6B C1B 1.5(9) . . . . ?
C4B C5B C6B C7B -178.6(7) . . . . ?
C5B C6B C7B C8B 179.9(7) . . . . ?
C6B C1B C2B C3B -0.5(8) . . . . ?
C6B C1B C2B C8B -179.8(5) . . . 2_655 ?
C6B C7B C8B C2B 0.1(11) . . . 2_655 ?
C8B C2B C3B C4B 179.4(7) 2_655 . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DCM'
####################################################################### 
# 
# 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_JV15_transazo_anthracene_01_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2240205'
loop_
_audit_author_name
_audit_author_address
'Jogirdas Vainauskas'
;McGill University, University of Birmingham
Canada
;
_audit_update_record             
;
2023-04-25 deposited with the CCDC.	2023-10-09 downloaded from the CCDC.
;
_audit_creation_date             2021-12-09
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
# start Validation Reply Form
_vrf_PLAT342_JV15_transazo_anthracene_01_0m_a 
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.02105 Ang.  
RESPONSE: This is most likely due to thermal motion, arising from
data collection at room temperature.
;
# end Validation Reply Form
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 F8 I2 N2, 0.5(C14 H10)'
_chemical_formula_sum            'C19 H5 F8 I2 N2'
_chemical_formula_weight         667.05
_chemical_melting_point          ?
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'

_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                   5.9146(8)
_cell_length_b                   9.8631(14)
_cell_length_c                   17.9820(18)
_cell_angle_alpha                94.026(5)
_cell_angle_beta                 97.548(5)
_cell_angle_gamma                105.520(6)
_cell_volume                     995.9(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6472
_cell_measurement_temperature    298
_cell_measurement_theta_max      72.50
_cell_measurement_theta_min      4.69
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    25.594
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.1479
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Krause, Herbst-Irmer, Sheldrick & Stalke, 2015)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange-red
_exptl_crystal_density_diffrn    2.224
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             622
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.075
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0711
_diffrn_reflns_av_unetI/netI     0.0645
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            14419
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.555
_diffrn_reflns_theta_min         2.494
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  
'Bruker D8 Venture, Dual, Cu at zero, PHOTON II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2884
_reflns_number_total             3908
_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       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         1.090
_refine_diff_density_min         -0.917
_refine_diff_density_rms         0.191
_refine_ls_extinction_coef       0.0030(5)
_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   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3908
_refine_ls_number_restraints     216
_refine_ls_R_factor_all          0.1068
_refine_ls_R_factor_gt           0.0827
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0716P)²+19.0170P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2207
_refine_ls_wR_factor_ref         0.2396
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Aromatic/amide H refined with riding coordinates:
 C1B(H1B), C2B(H2B), C3B(H3B), C4B(H4B), C6B(H6B)
;
_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
I1A I 1.64357(19) 0.22097(13) 0.77197(5) 0.0745(5) Uani 1 1 d . . . . .
N2A N 0.911(3) 0.2145(16) 0.4319(7) 0.072(3) Uani 1 1 d . . . . .
I2A I 0.22054(17) 0.30312(13) 0.15289(5) 0.0724(5) Uani 1 1 d . . . . .
F1A F 1.2569(16) 0.3897(11) 0.7470(5) 0.072(2) Uani 1 1 d . . . . .
F2A F 0.9582(17) 0.4058(11) 0.6265(5) 0.077(3) Uani 1 1 d . . . . .
F3A F 1.255(2) 0.0962(11) 0.4820(5) 0.083(3) Uani 1 1 d . . . . .
F4A F 1.5533(18) 0.0827(10) 0.6012(5) 0.077(3) Uani 1 1 d . . . . .
F5A F 0.5650(19) 0.3818(11) 0.4466(5) 0.081(3) Uani 1 1 d . . . . .
F6A F 0.2796(18) 0.4094(12) 0.3269(6) 0.081(3) Uani 1 1 d . . . . .
F7A F 0.6132(16) 0.1357(11) 0.1727(5) 0.074(2) Uani 1 1 d . . . . .
F8A F 0.8985(18) 0.1007(11) 0.2922(5) 0.079(3) Uani 1 1 d . . . . .
C1A C 1.416(2) 0.2340(14) 0.6776(6) 0.047(2) Uani 1 1 d . . . . .
N1A N 0.925(2) 0.2763(14) 0.4908(7) 0.067(3) Uani 1 1 d . . . . .
C2A C 1.259(2) 0.3158(14) 0.6824(7) 0.050(3) Uani 1 1 d . . . . .
C3A C 1.101(2) 0.3259(15) 0.6194(7) 0.052(3) Uani 1 1 d . . . . .
C4A C 1.094(2) 0.2541(15) 0.5495(7) 0.052(3) Uani 1 1 d . . . . .
C5A C 1.253(3) 0.1693(14) 0.5462(7) 0.052(3) Uani 1 1 d . . . . .
C6A C 1.410(2) 0.1629(14) 0.6089(7) 0.049(3) Uani 1 1 d . . . . .
C7A C 0.746(2) 0.2396(16) 0.3739(8) 0.057(3) Uani 1 1 d . . . . .
C8A C 0.581(2) 0.3179(15) 0.3806(7) 0.054(3) Uani 1 1 d . . . . .
C9A C 0.432(2) 0.3352(17) 0.3181(7) 0.057(3) Uani 1 1 d . . . . .
C10A C 0.438(2) 0.2748(14) 0.2474(7) 0.048(3) Uani 1 1 d . . . . .
C11A C 0.601(2) 0.1960(15) 0.2403(7) 0.051(3) Uani 1 1 d . . . . .
C12A C 0.744(2) 0.1804(15) 0.3021(8) 0.055(3) Uani 1 1 d . . . . .
C1B C 0.169(3) 0.297(2) -0.0773(8) 0.077(4) Uani 1 1 d . . . . .
H1B H 0.302681 0.323299 -0.100697 0.092 Uiso 1 1 calc R U . . .
C2B C 0.052(4) 0.159(2) -0.0801(9) 0.082(4) Uani 1 1 d . . . . .
H2B H 0.112706 0.093272 -0.104031 0.098 Uiso 1 1 calc R U . . .
C3B C -0.158(4) 0.108(2) -0.0493(9) 0.089(4) Uani 1 1 d . . . . .
H3B H -0.237023 0.011640 -0.053933 0.107 Uiso 1 1 calc R U . . .
C4B C -0.237(3) 0.208(2) -0.0120(9) 0.077(4) Uani 1 1 d . . . . .
H4B H -0.372858 0.177678 0.010275 0.092 Uiso 1 1 calc R U . . .
C5B C -0.124(2) 0.3522(18) -0.0060(7) 0.059(3) Uani 1 1 d . . . . .
C6B C -0.201(3) 0.4553(19) 0.0325(7) 0.063(3) Uani 1 1 d . . . . .
H6B H -0.335752 0.425516 0.055254 0.076 Uiso 1 1 calc R U . . .
C7B C -0.089(2) 0.5990(18) 0.0388(7) 0.060(3) 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
I1A C1A 2.057(11) . ?
N2A N1A 1.167(18) . ?
N2A C7A 1.415(19) . ?
I2A C10A 2.076(12) . ?
F1A C2A 1.331(15) . ?
F2A C3A 1.312(16) . ?
F3A C5A 1.320(15) . ?
F4A C6A 1.321(16) . ?
F5A C8A 1.330(15) . ?
F6A C9A 1.321(17) . ?
F7A C11A 1.333(15) . ?
F8A C12A 1.375(17) . ?
C1A C2A 1.390(19) . ?
C1A C6A 1.368(17) . ?
N1A C4A 1.426(17) . ?
C2A C3A 1.398(18) . ?
C3A C4A 1.389(18) . ?
C4A C5A 1.42(2) . ?
C5A C6A 1.378(18) . ?
C7A C8A 1.41(2) . ?
C7A C12A 1.38(2) . ?
C8A C9A 1.383(19) . ?
C9A C10A 1.376(18) . ?
C10A C11A 1.401(19) . ?
C11A C12A 1.350(18) . ?
C1B H1B 0.9300 . ?
C1B C2B 1.34(3) . ?
C1B C7B 1.42(2) 2_565 ?
C2B H2B 0.9300 . ?
C2B C3B 1.41(3) . ?
C3B H3B 0.9300 . ?
C3B C4B 1.37(3) . ?
C4B H4B 0.9300 . ?
C4B C5B 1.39(2) . ?
C5B C6B 1.40(2) . ?
C5B C7B 1.44(2) 2_565 ?
C6B H6B 0.9300 . ?
C6B C7B 1.38(2) . ?

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
N1A N2A C7A 115.3(14) . . ?
C2A C1A I1A 120.1(9) . . ?
C6A C1A I1A 122.4(10) . . ?
C6A C1A C2A 117.5(11) . . ?
N2A N1A C4A 115.9(14) . . ?
F1A C2A C1A 121.1(11) . . ?
F1A C2A C3A 117.5(12) . . ?
C1A C2A C3A 121.4(11) . . ?
F2A C3A C2A 119.2(12) . . ?
F2A C3A C4A 119.6(12) . . ?
C4A C3A C2A 121.3(13) . . ?
C3A C4A N1A 114.4(13) . . ?
C3A C4A C5A 116.3(11) . . ?
C5A C4A N1A 129.2(12) . . ?
F3A C5A C4A 120.0(12) . . ?
F3A C5A C6A 118.8(13) . . ?
C6A C5A C4A 121.2(12) . . ?
F4A C6A C1A 120.1(11) . . ?
F4A C6A C5A 117.7(12) . . ?
C1A C6A C5A 122.2(13) . . ?
C8A C7A N2A 127.8(13) . . ?
C12A C7A N2A 116.6(14) . . ?
C12A C7A C8A 115.6(12) . . ?
F5A C8A C7A 121.8(12) . . ?
F5A C8A C9A 116.9(13) . . ?
C9A C8A C7A 121.2(12) . . ?
F6A C9A C8A 119.3(13) . . ?
F6A C9A C10A 119.7(12) . . ?
C10A C9A C8A 120.9(14) . . ?
C9A C10A I2A 121.3(10) . . ?
C9A C10A C11A 118.2(12) . . ?
C11A C10A I2A 120.5(9) . . ?
F7A C11A C10A 120.1(11) . . ?
F7A C11A C12A 120.0(13) . . ?
C12A C11A C10A 119.8(12) . . ?
F8A C12A C7A 118.3(12) . . ?
C11A C12A F8A 117.5(13) . . ?
C11A C12A C7A 124.2(14) . . ?
C2B C1B H1B 119.9 . . ?
C2B C1B C7B 120.1(18) . 2_565 ?
C7B C1B H1B 119.9 2_565 . ?
C1B C2B H2B 117.7 . . ?
C1B C2B C3B 124.5(19) . . ?
C3B C2B H2B 117.7 . . ?
C2B C3B H3B 122.0 . . ?
C4B C3B C2B 116(2) . . ?
C4B C3B H3B 122.0 . . ?
C3B C4B H4B 118.6 . . ?
C3B C4B C5B 122.8(19) . . ?
C5B C4B H4B 118.6 . . ?
C4B C5B C6B 123.5(15) . . ?
C4B C5B C7B 119.6(16) . 2_565 ?
C6B C5B C7B 116.9(15) . 2_565 ?
C5B C6B H6B 118.1 . . ?
C7B C6B C5B 123.9(14) . . ?
C7B C6B H6B 118.1 . . ?
C1B C7B C5B 116.9(16) 2_565 2_565 ?
C6B C7B C1B 123.8(15) . 2_565 ?
C6B C7B C5B 119.3(14) . 2_565 ?

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
I1A C1A C2A F1A 1.8(18) . . . . ?
I1A C1A C2A C3A -179.5(10) . . . . ?
I1A C1A C6A F4A -0.3(18) . . . . ?
I1A C1A C6A C5A 178.5(10) . . . . ?
N2A N1A C4A C3A -178.2(15) . . . . ?
N2A N1A C4A C5A 1(2) . . . . ?
N2A C7A C8A F5A 1(2) . . . . ?
N2A C7A C8A C9A 178.9(15) . . . . ?
N2A C7A C12A F8A 1(2) . . . . ?
N2A C7A C12A C11A -178.8(14) . . . . ?
I2A C10A C11A F7A -1.5(17) . . . . ?
I2A C10A C11A C12A 178.9(10) . . . . ?
F1A C2A C3A F2A 0(2) . . . . ?
F1A C2A C3A C4A 178.9(13) . . . . ?
F2A C3A C4A N1A 0(2) . . . . ?
F2A C3A C4A C5A -179.8(13) . . . . ?
F3A C5A C6A F4A 0(2) . . . . ?
F3A C5A C6A C1A -179.1(13) . . . . ?
F5A C8A C9A F6A -2(2) . . . . ?
F5A C8A C9A C10A 179.0(13) . . . . ?
F6A C9A C10A I2A 2.0(19) . . . . ?
F6A C9A C10A C11A -179.5(13) . . . . ?
F7A C11A C12A F8A 0(2) . . . . ?
F7A C11A C12A C7A 179.4(13) . . . . ?
C1A C2A C3A F2A -179.2(13) . . . . ?
C1A C2A C3A C4A 0(2) . . . . ?
N1A N2A C7A C8A -7(2) . . . . ?
N1A N2A C7A C12A 173.2(15) . . . . ?
N1A C4A C5A F3A -1(2) . . . . ?
N1A C4A C5A C6A 178.5(14) . . . . ?
C2A C1A C6A F4A -179.5(12) . . . . ?
C2A C1A C6A C5A -1(2) . . . . ?
C2A C3A C4A N1A -179.4(13) . . . . ?
C2A C3A C4A C5A 1(2) . . . . ?
C3A C4A C5A F3A 179.0(13) . . . . ?
C3A C4A C5A C6A -2(2) . . . . ?
C4A C5A C6A F4A -179.4(13) . . . . ?
C4A C5A C6A C1A 2(2) . . . . ?
C6A C1A C2A F1A -179.0(12) . . . . ?
C6A C1A C2A C3A 0(2) . . . . ?
C7A N2A N1A C4A -178.9(12) . . . . ?
C7A C8A C9A F6A 180.0(13) . . . . ?
C7A C8A C9A C10A 1(2) . . . . ?
C8A C7A C12A F8A -178.9(12) . . . . ?
C8A C7A C12A C11A 1(2) . . . . ?
C8A C9A C10A I2A -178.8(11) . . . . ?
C8A C9A C10A C11A 0(2) . . . . ?
C9A C10A C11A F7A -180.0(13) . . . . ?
C9A C10A C11A C12A 0(2) . . . . ?
C10A C11A C12A F8A 179.3(12) . . . . ?
C10A C11A C12A C7A -1(2) . . . . ?
C12A C7A C8A F5A -179.3(13) . . . . ?
C12A C7A C8A C9A -1(2) . . . . ?
C1B C2B C3B C4B -2(2) . . . . ?
C2B C3B C4B C5B 2(2) . . . . ?
C3B C4B C5B C6B -179.3(14) . . . . ?
C3B C4B C5B C7B -1(2) . . . 2_565 ?
C4B C5B C6B C7B 179.9(12) . . . . ?
C5B C6B C7B C1B 179.5(12) . . . 2_565 ?
C5B C6B C7B C5B -2(2) . . . 2_565 ?
C7B C1B C2B C3B 3(2) 2_565 . . . ?
C7B C5B C6B C7B 1.8(19) 2_565 . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DCM'
####################################################################### 
# 
# 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_s12runs_a
_database_code_depnum_ccdc_archive 'CCDC 2240204'
loop_
_audit_author_name
_audit_author_address
'Jogirdas Vainauskas'
;McGill University, University of Birmingham
Canada
;
_audit_update_record             
;
2023-04-25 deposited with the CCDC.	2023-10-09 downloaded from the CCDC.
;
_audit_creation_date             2022-01-13
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
#start Validation Reply Form
_vrf_PLAT971_s12runs_a           
;
PROBLEM: Check Calcd Resid. Dens.  0.90Ang From I2A             3.24 eA-3  
RESPONSE: The large residual densities are located on heavy iodine atoms, 
and most likely originate from absorption correction issues or Fourier
truncation error.
;
_vrf_PLAT250_s12runs_a           
;
PROBLEM: Large U3/U1 Ratio for Average U(i,j) Tensor ....        4.8 Note  
RESPONSE: This is likely due to thermal motion of the coronene unit.
;
# end Validation Reply Form
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C6 F4 I2), C24 H12'
_chemical_formula_sum            'C36 H12 F8 I4'
_chemical_formula_weight         1104.06
_chemical_melting_point          ?
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'

_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                   5.7028(6)
_cell_length_b                   10.2278(12)
_cell_length_c                   14.3969(15)
_cell_angle_alpha                104.396(6)
_cell_angle_beta                 97.493(5)
_cell_angle_gamma                95.668(6)
_cell_volume                     798.86(15)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    4866
_cell_measurement_temperature    183(2)
_cell_measurement_theta_max      71.86
_cell_measurement_theta_min      4.51
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    31.298
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.1942
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Krause, Herbst-Irmer, Sheldrick & Stalke, 2015)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.295
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0494
_diffrn_reflns_av_unetI/netI     0.0496
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10608
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.747
_diffrn_reflns_theta_min         4.505
_diffrn_ambient_temperature      183(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  
'Bruker D8 Venture, Dual, Cu at zero, PHOTON II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'micro-focus sealed X-ray tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2344
_reflns_number_total             3107
_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       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         3.305
_refine_diff_density_min         -2.269
_refine_diff_density_rms         0.184
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3107
_refine_ls_number_restraints     174
_refine_ls_R_factor_all          0.0889
_refine_ls_R_factor_gt           0.0697
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0686P)²+9.6729P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1745
_refine_ls_wR_factor_ref         0.1923
_refine_special_details          ?
_olex2_refinement_description    
;
1. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
2.a Aromatic/amide H refined with riding coordinates:
 C1B(H1B), C2B(H2B), C4B(H4B), C5B(H5B), C7B(H7B), C8B(H8B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
I1A I 0.88404(14) 0.20987(10) 0.63309(6) 0.0681(3) Uani 1 1 d . . . . .
F1A F 0.7362(17) 0.0401(9) 0.4070(6) 0.091(3) Uani 1 1 d . . . . .
I2A I 0.01482(13) 0.27155(10) 0.26431(6) 0.0699(3) Uani 1 1 d . . . . .
F2A F 0.4057(16) 0.0649(8) 0.2663(5) 0.080(2) Uani 1 1 d . . . . .
F3A F 0.1698(17) 0.4326(10) 0.4858(6) 0.096(3) Uani 1 1 d . . . . .
F4A F 0.5011(16) 0.4106(9) 0.6255(5) 0.089(3) Uani 1 1 d . . . . .
C1A C 0.6259(18) 0.2244(12) 0.5212(7) 0.048(2) Uani 1 1 d . . . . .
C2A C 0.594(2) 0.1374(12) 0.4268(8) 0.051(2) Uani 1 1 d . . . . .
C3A C 0.423(2) 0.1504(12) 0.3550(7) 0.054(2) Uani 1 1 d . . . . .
C4A C 0.2756(18) 0.2486(11) 0.3728(7) 0.048(2) Uani 1 1 d . . . . .
C5A C 0.302(2) 0.3332(13) 0.4650(8) 0.058(3) Uani 1 1 d . . . . .
C6A C 0.481(2) 0.3210(13) 0.5380(7) 0.056(3) Uani 1 1 d . . . . .
C1B C -0.338(3) 0.7123(18) 1.1695(9) 0.084(4) Uani 1 1 d . . . . .
H1B H -0.445610 0.738576 1.213693 0.101 Uiso 1 1 calc R U . . .
C2B C -0.197(3) 0.8113(16) 1.1459(10) 0.082(3) Uani 1 1 d . . . . .
H2B H -0.211337 0.904255 1.173162 0.099 Uiso 1 1 calc R U . . .
C3B C -0.035(3) 0.7797(12) 1.0839(9) 0.068(3) Uani 1 1 d . . . . .
C4B C 0.109(3) 0.8769(13) 1.0582(10) 0.084(3) Uani 1 1 d . . . . .
H4B H 0.099891 0.970579 1.085650 0.101 Uiso 1 1 calc R U . . .
C5B C 0.266(3) 0.8410(13) 0.9928(9) 0.075(3) Uani 1 1 d . . . . .
H5B H 0.359244 0.910618 0.975111 0.090 Uiso 1 1 calc R U . . .
C6B C 0.291(2) 0.7069(13) 0.9535(8) 0.067(3) Uani 1 1 d . . . . .
C7B C 0.454(3) 0.6681(19) 0.8908(9) 0.085(3) Uani 1 1 d . . . . .
H7B H 0.554783 0.736866 0.875536 0.102 Uiso 1 1 calc R U . . .
C8B C 0.474(3) 0.533(2) 0.8505(9) 0.083(3) Uani 1 1 d . . . . .
H8B H 0.588418 0.511955 0.808705 0.100 Uiso 1 1 calc R U . . .
C9B C 0.329(2) 0.4260(16) 0.8693(8) 0.068(3) Uani 1 1 d . . . . .
C10B C 0.1649(19) 0.4638(12) 0.9342(7) 0.051(2) Uani 1 1 d . . . . .
C11B C 0.146(2) 0.6025(11) 0.9761(7) 0.052(2) Uani 1 1 d . . . . .
C12B C -0.013(2) 0.6398(11) 1.0417(7) 0.051(2) 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
I1A C1A 2.080(9) . ?
F1A C2A 1.344(12) . ?
I2A C4A 2.086(10) . ?
F2A C3A 1.342(12) . ?
F3A C5A 1.323(13) . ?
F4A C6A 1.345(12) . ?
C1A C2A 1.405(14) . ?
C1A C6A 1.346(15) . ?
C2A C3A 1.367(15) . ?
C3A C4A 1.371(16) . ?
C4A C5A 1.373(15) . ?
C5A C6A 1.404(14) . ?
C1B H1B 0.9500 . ?
C1B C2B 1.37(2) . ?
C1B C9B 1.40(2) 2_567 ?
C2B H2B 0.9500 . ?
C2B C3B 1.37(2) . ?
C3B C4B 1.38(2) . ?
C3B C12B 1.433(16) . ?
C4B H4B 0.9500 . ?
C4B C5B 1.40(2) . ?
C5B H5B 0.9500 . ?
C5B C6B 1.376(19) . ?
C6B C7B 1.40(2) . ?
C6B C11B 1.413(16) . ?
C7B H7B 0.9500 . ?
C7B C8B 1.38(2) . ?
C8B H8B 0.9500 . ?
C8B C9B 1.41(2) . ?
C9B C10B 1.420(17) . ?
C10B C11B 1.418(16) . ?
C10B C12B 1.439(16) 2_567 ?
C11B C12B 1.404(17) . ?

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
C2A C1A I1A 123.0(7) . . ?
C6A C1A I1A 119.7(7) . . ?
C6A C1A C2A 117.3(9) . . ?
F1A C2A C1A 119.1(9) . . ?
F1A C2A C3A 119.5(10) . . ?
C3A C2A C1A 121.3(10) . . ?
F2A C3A C2A 118.1(10) . . ?
F2A C3A C4A 120.9(9) . . ?
C2A C3A C4A 121.0(10) . . ?
C3A C4A I2A 121.8(7) . . ?
C3A C4A C5A 118.4(9) . . ?
C5A C4A I2A 119.8(8) . . ?
F3A C5A C4A 121.0(10) . . ?
F3A C5A C6A 118.6(10) . . ?
C4A C5A C6A 120.3(10) . . ?
F4A C6A C1A 121.5(9) . . ?
F4A C6A C5A 116.8(10) . . ?
C1A C6A C5A 121.7(10) . . ?
C2B C1B H1B 119.0 . . ?
C2B C1B C9B 122.0(15) . 2_567 ?
C9B C1B H1B 119.0 2_567 . ?
C1B C2B H2B 119.2 . . ?
C1B C2B C3B 121.6(14) . . ?
C3B C2B H2B 119.2 . . ?
C2B C3B C4B 123.1(14) . . ?
C2B C3B C12B 119.7(14) . . ?
C4B C3B C12B 117.2(14) . . ?
C3B C4B H4B 119.2 . . ?
C3B C4B C5B 121.5(13) . . ?
C5B C4B H4B 119.2 . . ?
C4B C5B H5B 119.3 . . ?
C6B C5B C4B 121.3(13) . . ?
C6B C5B H5B 119.3 . . ?
C5B C6B C7B 122.6(13) . . ?
C5B C6B C11B 119.7(14) . . ?
C7B C6B C11B 117.7(13) . . ?
C6B C7B H7B 119.0 . . ?
C8B C7B C6B 122.1(14) . . ?
C8B C7B H7B 119.0 . . ?
C7B C8B H8B 119.0 . . ?
C7B C8B C9B 122.0(14) . . ?
C9B C8B H8B 119.0 . . ?
C1B C9B C8B 125.0(14) 2_567 . ?
C1B C9B C10B 118.4(14) 2_567 . ?
C8B C9B C10B 116.6(13) . . ?
C9B C10B C12B 119.9(11) . 2_567 ?
C11B C10B C9B 121.4(12) . . ?
C11B C10B C12B 118.7(10) . 2_567 ?
C6B C11B C10B 120.2(12) . . ?
C12B C11B C6B 118.4(11) . . ?
C12B C11B C10B 121.4(10) . . ?
C3B C12B C10B 118.3(12) . 2_567 ?
C11B C12B C3B 121.8(12) . . ?
C11B C12B C10B 119.9(10) . 2_567 ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DCM'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_s7_a
_audit_block_doi                 10.5517/ccdc.csd.cc2f63h8
_database_code_depnum_ccdc_archive 'CCDC 2240199'
loop_
_citation_id
_citation_doi
_citation_year
1 10.26434/chemrxiv-2023-wnhrf 2023
loop_
_audit_author_name
_audit_author_address
'Jogirdas Vainauskas'
;McGill University, University of Birmingham
Canada
;
_audit_update_record             
;
2023-04-25 deposited with the CCDC.	2023-10-09 downloaded from the CCDC.
;
_audit_creation_date             2023-04-12
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
# start Validation Reply Form
_vrf_PLAT971_s7_a                
;
PROBLEM: Check Calcd Resid. Dens. 0.96Ang From I1A 4.29 eA-3
RESPONSE: The large residual densities are located on heavy iodine atoms, 
and originates from absorption correction issues or Fourier
truncation error.
;
_vrf_PLAT112_s7_a                
;
PROBLEM: ADDSYM Detects New (Pseudo) Symm. Elem m 100 %Fit
RESPONSE: Attempts to solve the structure in a monoclinic space group 
were unsuccessful, suggesting the original triclinic space group is correct.
;
_vrf_PLAT113_s7_a                
;
PROBLEM: ADDSYM Suggests Possible Pseudo/New Space Group C2/m Check
RESPONSE: Attempts to solve the structure in a monoclinic space group 
were unsuccessful, suggesting the original triclinic space group is correct.
;
_vrf_PLAT331_s7_a                
;
PROBLEM: Small Aver Phenyl C-C Dist C1B      --C3B_b    .       1.36 Ang.  
RESPONSE: This is most likely due to thermal motion.
;
_vrf_PLAT342_s7_a                
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............      0.023 Ang.  
RESPONSE: This is most likely due to thermal motion.
;
# end Validation Reply Form
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 F4 I2, C6 H6'
_chemical_formula_sum            'C12 H6 F4 I2'
_chemical_formula_weight         479.97
_chemical_melting_point          ?
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'

_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                   5.6444(7)
_cell_length_b                   5.6487(7)
_cell_length_c                   10.5675(13)
_cell_angle_alpha                90.233(7)
_cell_angle_beta                 90.118(7)
_cell_angle_gamma                100.763(8)
_cell_volume                     331.00(7)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    3076
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      72.34
_cell_measurement_theta_min      4.18
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    37.606
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.1342
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1839 before and 0.0831 after correction.
The Ratio of minimum to maximum transmission is 0.1781.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.402
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             219
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.170
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0731
_diffrn_reflns_av_unetI/netI     0.0695
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3945
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.519
_diffrn_reflns_theta_min         4.183
_diffrn_ambient_temperature      180
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1151
_reflns_number_total             1273
_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       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         4.273
_refine_diff_density_min         -2.400
_refine_diff_density_rms         0.519
_refine_ls_extinction_coef       0.029(5)
_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   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     83
_refine_ls_number_reflns         1273
_refine_ls_number_restraints     37
_refine_ls_R_factor_all          0.0959
_refine_ls_R_factor_gt           0.0910
_refine_ls_restrained_S_all      1.080
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1847P)²+0.5300P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2171
_refine_ls_wR_factor_ref         0.2304
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Aromatic/amide H refined with riding coordinates:
 C1B(H1B), C3B(H3B), C2B(H2B)
;
_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
I1A I 0.82224(12) 0.17804(12) 0.80380(6) 0.0377(6) Uani 1 1 d . . . . .
F1A F 0.4645(15) 0.5368(16) 0.7453(6) 0.0393(17) Uani 1 1 d . . . . .
F2A F 0.2159(18) 0.7844(18) 0.8949(8) 0.048(2) Uani 1 1 d . . . . .
C2A C 0.483(2) 0.516(2) 0.8717(11) 0.034(2) Uani 1 1 d . . . . .
C1A C 0.628(2) 0.368(2) 0.9189(11) 0.030(2) Uani 1 1 d . . . . .
C1B C -0.004(4) 0.192(3) 0.4260(13) 0.056(4) Uani 1 1 d . . . . .
H1B H -0.007855 0.327155 0.372898 0.068 Uiso 1 1 calc R U . . .
C3A C 0.358(2) 0.645(2) 0.9485(11) 0.030(2) Uani 1 1 d . . . . .
C3B C 0.199(3) -0.003(4) 0.5736(13) 0.056(4) Uani 1 1 d . . . . .
H3B H 0.336680 -0.007590 0.624543 0.068 Uiso 1 1 calc R U . . .
C2B C 0.190(3) 0.189(3) 0.4996(15) 0.058(3) Uani 1 1 d . . . . .
H2B H 0.320283 0.321821 0.499502 0.070 Uiso 1 1 calc R U . . .


_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
I1A C1A 2.066(12) . ?
F1A C2A 1.347(14) . ?
F2A C3A 1.349(14) . ?
C2A C1A 1.369(18) . ?
C2A C3A 1.372(18) . ?
C1A C3A 1.406(16) 2_667 ?
C1B H1B 0.9500 . ?
C1B C3B 1.38(3) 2_556 ?
C1B C2B 1.35(3) . ?
C3B H3B 0.9500 . ?
C3B C2B 1.35(3) . ?
C2B H2B 0.9500 . ?

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
F1A C2A C1A 118.8(12) . . ?
F1A C2A C3A 118.9(12) . . ?
C1A C2A C3A 122.3(11) . . ?
C2A C1A I1A 122.5(9) . . ?
C2A C1A C3A 116.3(12) . 2_667 ?
C3A C1A I1A 121.2(9) 2_667 . ?
C3B C1B H1B 119.6 2_556 . ?
C2B C1B H1B 119.6 . . ?
C2B C1B C3B 120.9(15) . 2_556 ?
F2A C3A C2A 118.9(11) . . ?
F2A C3A C1A 119.7(11) . 2_667 ?
C2A C3A C1A 121.4(12) . 2_667 ?
C1B C3B H3B 120.6 2_556 . ?
C2B C3B C1B 118.9(15) . 2_556 ?
C2B C3B H3B 120.6 . . ?
C1B C2B C3B 120.2(15) . . ?
C1B C2B H2B 119.9 . . ?
C3B C2B H2B 119.9 . . ?

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
F1A C2A C1A I1A 0.4(17) . . . . ?
F1A C2A C1A C3A 179.6(10) . . . 2_667 ?
F1A C2A C3A F2A 1.5(19) . . . . ?
F1A C2A C3A C1A -179.6(10) . . . 2_667 ?
C1A C2A C3A F2A -179.1(11) . . . . ?
C1A C2A C3A C1A 0(2) . . . 2_667 ?
C1B C3B C2B C1B -1(2) 2_556 . . . ?
C3A C2A C1A I1A -178.9(9) . . . . ?
C3A C2A C1A C3A 0(2) . . . 2_667 ?
C3B C1B C2B C3B 1(2) 2_556 . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Benzene'
####################################################################### 
# 
# 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_sfulldata_a
_database_code_depnum_ccdc_archive 'CCDC 2240203'
loop_
_audit_author_name
_audit_author_address
'Jogirdas Vainauskas'
;McGill University, University of Birmingham
Canada
;
_audit_update_record             
;
2023-04-25 deposited with the CCDC.	2023-10-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H12, C6 F4 I2'
_chemical_formula_sum            'C24 H12 F4 I2'
_chemical_formula_weight         630.14

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   19.1824(19)
_cell_length_b                   5.9202(7)
_cell_length_c                   8.9814(9)
_cell_angle_alpha                90
_cell_angle_beta                 90.617(6)
_cell_angle_gamma                90
_cell_volume                     1019.90(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    5318
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      72.32

_exptl_crystal_description       lath
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.052
_exptl_crystal_F_000             596
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.152
_exptl_crystal_size_min          0.043
_exptl_absorpt_coefficient_mu    24.621
_shelx_estimated_absorpt_T_min   0.110
_shelx_estimated_absorpt_T_max   0.417
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3124
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1577 before and 0.0646 after correction.
The Ratio of minimum to maximum transmission is 0.8273.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_diffrn_measurement_device_type  
'Bruker D8 Venture, Dual, Cu at zero, PHOTON II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_detector_area_resol_mean ?
_diffrn_ambient_temperature      298
_diffrn_reflns_number            15463
_diffrn_reflns_av_unetI/netI     0.0451
_diffrn_reflns_av_R_equivalents  0.0806
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.303
_diffrn_reflns_theta_max         72.539
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2020
_reflns_number_gt                1621
_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       ?
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0131P)²+6.4952P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.00090(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2020
_refine_ls_number_parameters     137
_refine_ls_number_restraints     73
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0464
_refine_ls_wR_factor_ref         0.1107
_refine_ls_wR_factor_gt          0.0995
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.000
_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
C1A C 0.1395(3) 0.2846(11) 0.2118(7) 0.0412(13) Uani 1 1 d . . . . .
H1A H 0.127385 0.145364 0.171147 0.049 Uiso 1 1 calc R U . . .
C2A C 0.1988(3) 0.3895(13) 0.1671(7) 0.0464(15) Uani 1 1 d . . . . .
H2A H 0.227071 0.319885 0.097156 0.056 Uiso 1 1 calc R U . . .
C3A C 0.2182(3) 0.6024(13) 0.2252(8) 0.0493(15) Uani 1 1 d . . . . .
H3A H 0.258501 0.672538 0.191883 0.059 Uiso 1 1 calc R U . . .
C4A C 0.1786(3) 0.7048(11) 0.3288(7) 0.0413(14) Uani 1 1 d . . . . .
H4A H 0.192943 0.842831 0.368079 0.050 Uiso 1 1 calc R U . . .
C5A C 0.1150(3) 0.6051(10) 0.3795(6) 0.0349(12) Uani 1 1 d . . . . .
C6A C 0.0718(3) 0.7096(10) 0.4827(6) 0.0349(12) Uani 1 1 d . . . . .
H6A H 0.084686 0.849070 0.521945 0.042 Uiso 1 1 calc R U . . .
C7A C 0.0099(3) 0.6105(9) 0.5284(6) 0.0312(11) Uani 1 1 d . . . . .
C8A C -0.0341(3) 0.7121(9) 0.6330(6) 0.0328(11) Uani 1 1 d . . . . .
H8A H -0.021292 0.851311 0.672770 0.039 Uiso 1 1 calc R U . . .
C9A C -0.0955(3) 0.6138(10) 0.6794(6) 0.0336(12) Uani 1 1 d . . . . .
I1B I 0.34820(2) 0.22516(10) 0.34542(5) 0.0632(3) Uani 1 1 d . . . . .
F1B F 0.5058(2) 0.3958(7) 0.3513(5) 0.0626(11) Uani 1 1 d . . . . .
F2B F 0.6223(2) 0.2210(7) 0.4644(5) 0.0642(11) Uani 1 1 d . . . . .
C1B C 0.4387(3) 0.0933(11) 0.4392(6) 0.0414(14) Uani 1 1 d . . . . .
C2B C 0.5022(3) 0.1986(10) 0.4249(7) 0.0416(13) Uani 1 1 d . . . . .
C3B C 0.5620(3) 0.1088(11) 0.4830(7) 0.0414(14) 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
C1A C2A 1.361(9) . ?
C1A C9A 1.431(8) 3_566 ?
C1A H1A 0.9300 . ?
C2A C3A 1.412(10) . ?
C2A H2A 0.9300 . ?
C3A C4A 1.351(9) . ?
C3A H3A 0.9300 . ?
C4A C5A 1.435(8) . ?
C4A H4A 0.9300 . ?
C5A C6A 1.395(8) . ?
C5A C9A 1.447(8) 3_566 ?
C6A C7A 1.390(8) . ?
C6A H6A 0.9300 . ?
C7A C8A 1.404(8) . ?
C7A C7A 1.452(11) 3_566 ?
C8A C9A 1.382(8) . ?
C8A H8A 0.9300 . ?
I1B C1B 2.075(6) . ?
F1B C2B 1.344(7) . ?
F2B C3B 1.347(7) . ?
C1B C2B 1.374(9) . ?
C1B C3B 1.386(9) 3_656 ?
C2B C3B 1.363(9) . ?

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
C2A C1A C9A 120.8(6) . 3_566 ?
C2A C1A H1A 119.6 . . ?
C9A C1A H1A 119.6 3_566 . ?
C1A C2A C3A 121.0(6) . . ?
C1A C2A H2A 119.5 . . ?
C3A C2A H2A 119.5 . . ?
C4A C3A C2A 120.5(6) . . ?
C4A C3A H3A 119.7 . . ?
C2A C3A H3A 119.7 . . ?
C3A C4A C5A 121.3(6) . . ?
C3A C4A H4A 119.3 . . ?
C5A C4A H4A 119.3 . . ?
C6A C5A C4A 122.8(6) . . ?
C6A C5A C9A 119.2(5) . 3_566 ?
C4A C5A C9A 118.0(5) . 3_566 ?
C7A C6A C5A 121.6(5) . . ?
C7A C6A H6A 119.2 . . ?
C5A C6A H6A 119.2 . . ?
C6A C7A C8A 122.5(5) . . ?
C6A C7A C7A 119.8(6) . 3_566 ?
C8A C7A C7A 117.7(6) . 3_566 ?
C9A C8A C7A 122.7(5) . . ?
C9A C8A H8A 118.6 . . ?
C7A C8A H8A 118.6 . . ?
C8A C9A C1A 122.7(5) . 3_566 ?
C8A C9A C5A 119.0(5) . 3_566 ?
C1A C9A C5A 118.3(5) 3_566 3_566 ?
C2B C1B C3B 116.9(6) . 3_656 ?
C2B C1B I1B 122.0(5) . . ?
C3B C1B I1B 121.1(5) 3_656 . ?
F1B C2B C3B 118.7(6) . . ?
F1B C2B C1B 119.4(6) . . ?
C3B C2B C1B 122.0(6) . . ?
F2B C3B C2B 118.8(6) . . ?
F2B C3B C1B 120.1(6) . 3_656 ?
C2B C3B C1B 121.1(6) . 3_656 ?

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
C9A C1A C2A C3A -0.8(9) 3_566 . . . ?
C1A C2A C3A C4A 1.2(10) . . . . ?
C2A C3A C4A C5A -2.0(10) . . . . ?
C3A C4A C5A C6A -177.9(6) . . . . ?
C3A C4A C5A C9A 2.3(9) . . . 3_566 ?
C4A C5A C6A C7A 179.1(5) . . . . ?
C9A C5A C6A C7A -1.1(8) 3_566 . . . ?
C5A C6A C7A C8A 179.5(5) . . . . ?
C5A C6A C7A C7A 1.9(10) . . . 3_566 ?
C6A C7A C8A C9A -179.6(5) . . . . ?
C7A C7A C8A C9A -2.1(9) 3_566 . . . ?
C7A C8A C9A C1A 178.7(5) . . . 3_566 ?
C7A C8A C9A C5A 1.3(8) . . . 3_566 ?
C3B C1B C2B F1B -179.6(5) 3_656 . . . ?
I1B C1B C2B F1B 1.7(8) . . . . ?
C3B C1B C2B C3B 0.6(10) 3_656 . . . ?
I1B C1B C2B C3B -178.1(5) . . . . ?
F1B C2B C3B F2B 0.1(9) . . . . ?
C1B C2B C3B F2B 179.9(6) . . . . ?
F1B C2B C3B C1B 179.6(6) . . . 3_656 ?
C1B C2B C3B C1B -0.6(11) . . . 3_656 ?

_refine_diff_density_max         0.730
_refine_diff_density_min         -1.276
_refine_diff_density_rms         0.125


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: 1,2,4-trichlorobenzene'
####################################################################### 
# 
# 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_s2_a
_database_code_depnum_ccdc_archive 'CCDC 2240202'
loop_
_audit_author_name
_audit_author_address
'Jogirdas Vainauskas'
;McGill University, University of Birmingham
Canada
;
_audit_update_record             
;
2023-04-25 deposited with the CCDC.	2023-10-09 downloaded from the CCDC.
;
_audit_creation_date             2022-01-20
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
# start Validation Reply Form
_vrf_PLAT972_s2_a                
;
PROBLEM: Check Calcd Resid. Dens.  0.65Ang From I3A            -3.14 eA-3  
RESPONSE: The large residual densities are located on heavy iodine atoms, 
and most likely originate from absorption correction issues or Fourier 
truncation error.
;
# end Validation Reply Form
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H12, 2(C6 F4 I2)'
_chemical_formula_sum            'C32 H12 F8 I4'
_chemical_formula_weight         1056.02
_chemical_melting_point          ?
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'

_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                   5.8113(2)
_cell_length_b                   10.2259(4)
_cell_length_c                   13.3298(4)
_cell_angle_alpha                103.6520(10)
_cell_angle_beta                 92.767(2)
_cell_angle_gamma                96.252(2)
_cell_volume                     762.93(5)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    6351
_cell_measurement_temperature    298
_cell_measurement_theta_max      72.47
_cell_measurement_theta_min      3.42
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    32.725
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.4691
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1839 before and 0.0831 after correction.
The Ratio of minimum to maximum transmission is 0.1781.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    2.298
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.130
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0667
_diffrn_reflns_av_unetI/netI     0.0589
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12061
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.392
_diffrn_reflns_theta_min         3.422
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  
'Bruker D8 Venture, Dual, Cu at zero, PHOTON II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'micro-focus sealed X-ray tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2436
_reflns_number_total             2980
_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       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         2.185
_refine_diff_density_min         -3.180
_refine_diff_density_rms         0.394
_refine_ls_extinction_coef       0.0230(18)
_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   1.100
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2980
_refine_ls_number_restraints     159
_refine_ls_R_factor_all          0.0950
_refine_ls_R_factor_gt           0.0857
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1568P)²+1.8196P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2115
_refine_ls_wR_factor_ref         0.2304
_refine_special_details          ?
_olex2_refinement_description    
;
1. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
2.a Aromatic/amide H refined with riding coordinates:
 C3B(H3B), C4B(H4B), C5B(H5B), C7B(H7B), C8B(H8B), C9B(H9B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
C1A C 0.3131(12) 0.7554(8) 0.3653(6) 0.0302(14) Uani 1 1 d . . . . .
I1A I 0.08535(11) 0.78156(7) 0.24912(5) 0.0538(4) Uani 1 1 d . . . . .
F2A F 0.4801(12) 0.9053(6) 0.6369(4) 0.0582(16) Uani 1 1 d . . . . .
C2A C 0.3226(14) 0.8366(8) 0.4654(6) 0.0339(16) Uani 1 1 d . . . . .
I3A I 0.86211(10) 0.70437(8) 0.63907(5) 0.0545(4) Uani 1 1 d . . . . .
F3A F 0.7537(14) 0.5450(8) 0.4010(5) 0.077(2) Uani 1 1 d . . . . .
C3A C 0.4751(14) 0.8215(8) 0.5418(5) 0.0318(15) Uani 1 1 d . . . . .
F4A F 0.4610(14) 0.5761(7) 0.2515(4) 0.0670(18) Uani 1 1 d . . . . .
C4A C 0.6243(13) 0.7242(8) 0.5235(6) 0.0305(14) Uani 1 1 d . . . . .
C5A C 0.6173(15) 0.6440(9) 0.4250(7) 0.0380(17) Uani 1 1 d . . . . .
C6A C 0.4640(15) 0.6586(8) 0.3478(6) 0.0357(16) Uani 1 1 d . . . . .
F1A F 0.1837(12) 0.9316(7) 0.4889(5) 0.0618(17) Uani 1 1 d . . . . .
C1B C -0.0074(12) 0.8553(7) 0.9659(5) 0.0233(12) Uani 1 1 d . . . . .
C2B C -0.1710(11) 0.9127(7) 1.0368(5) 0.0239(13) Uani 1 1 d . . . . .
C3B C -0.3280(14) 0.8238(8) 1.0708(6) 0.0363(16) Uani 1 1 d . . . . .
H3B H -0.434362 0.859018 1.116561 0.044 Uiso 1 1 calc R U . . .
C4B C -0.3325(16) 0.6789(9) 1.0379(8) 0.0447(19) Uani 1 1 d . . . . .
H4B H -0.437298 0.621734 1.063410 0.054 Uiso 1 1 calc R U . . .
C5B C -0.1852(16) 0.6283(8) 0.9708(7) 0.0415(17) Uani 1 1 d . . . . .
H5B H -0.191843 0.534582 0.948082 0.050 Uiso 1 1 calc R U . . .
C6B C -0.0179(13) 0.7116(7) 0.9325(5) 0.0304(14) Uani 1 1 d . . . . .
C7B C 0.1446(17) 0.6568(9) 0.8645(7) 0.0458(18) Uani 1 1 d . . . . .
H7B H 0.139673 0.563140 0.842078 0.055 Uiso 1 1 calc R U . . .
C8B C 0.3059(17) 0.7373(10) 0.8317(7) 0.048(2) Uani 1 1 d . . . . .
H8B H 0.411557 0.698740 0.786941 0.058 Uiso 1 1 calc R U . . .
C9B C 0.3180(13) 0.8767(8) 0.8631(5) 0.0306(15) Uani 1 1 d . . . . .
H9B H 0.431474 0.930130 0.838784 0.037 Uiso 1 1 calc R U . . .
C10B C 0.1635(12) 0.9398(7) 0.9309(5) 0.0240(13) 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
C1A I1A 2.072(7) . ?
C1A C2A 1.390(11) . ?
C1A C6A 1.380(11) . ?
F2A C3A 1.350(8) . ?
C2A C3A 1.364(11) . ?
C2A F1A 1.321(9) . ?
I3A C4A 2.080(7) . ?
F3A C5A 1.342(9) . ?
C3A C4A 1.377(11) . ?
F4A C6A 1.358(9) . ?
C4A C5A 1.371(11) . ?
C5A C6A 1.373(12) . ?
C1B C2B 1.445(10) . ?
C1B C6B 1.425(9) . ?
C1B C10B 1.414(10) . ?
C2B C3B 1.385(10) . ?
C2B C10B 1.463(10) 2_577 ?
C3B H3B 0.9300 . ?
C3B C4B 1.440(13) . ?
C4B H4B 0.9300 . ?
C4B C5B 1.323(14) . ?
C5B H5B 0.9300 . ?
C5B C6B 1.416(12) . ?
C6B C7B 1.409(12) . ?
C7B H7B 0.9300 . ?
C7B C8B 1.338(14) . ?
C8B H8B 0.9300 . ?
C8B C9B 1.381(13) . ?
C9B H9B 0.9300 . ?
C9B C10B 1.403(9) . ?

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
C2A C1A I1A 121.2(6) . . ?
C6A C1A I1A 122.4(6) . . ?
C6A C1A C2A 116.5(7) . . ?
C3A C2A C1A 121.5(7) . . ?
F1A C2A C1A 120.4(7) . . ?
F1A C2A C3A 118.1(7) . . ?
F2A C3A C2A 118.8(7) . . ?
F2A C3A C4A 119.7(7) . . ?
C2A C3A C4A 121.5(7) . . ?
C3A C4A I3A 121.5(6) . . ?
C5A C4A I3A 120.9(6) . . ?
C5A C4A C3A 117.6(7) . . ?
F3A C5A C4A 121.4(8) . . ?
F3A C5A C6A 117.4(8) . . ?
C4A C5A C6A 121.1(7) . . ?
F4A C6A C1A 118.9(7) . . ?
F4A C6A C5A 119.3(7) . . ?
C5A C6A C1A 121.8(7) . . ?
C6B C1B C2B 119.1(6) . . ?
C10B C1B C2B 120.8(6) . . ?
C10B C1B C6B 120.1(7) . . ?
C1B C2B C10B 119.1(6) . 2_577 ?
C3B C2B C1B 117.6(7) . . ?
C3B C2B C10B 123.3(7) . 2_577 ?
C2B C3B H3B 118.8 . . ?
C2B C3B C4B 122.4(8) . . ?
C4B C3B H3B 118.8 . . ?
C3B C4B H4B 120.5 . . ?
C5B C4B C3B 119.0(8) . . ?
C5B C4B H4B 120.5 . . ?
C4B C5B H5B 118.8 . . ?
C4B C5B C6B 122.4(8) . . ?
C6B C5B H5B 118.8 . . ?
C5B C6B C1B 119.4(7) . . ?
C7B C6B C1B 118.6(7) . . ?
C7B C6B C5B 122.0(7) . . ?
C6B C7B H7B 119.5 . . ?
C8B C7B C6B 121.0(8) . . ?
C8B C7B H7B 119.5 . . ?
C7B C8B H8B 119.5 . . ?
C7B C8B C9B 121.0(8) . . ?
C9B C8B H8B 119.5 . . ?
C8B C9B H9B 119.2 . . ?
C8B C9B C10B 121.7(8) . . ?
C10B C9B H9B 119.2 . . ?
C1B C10B C2B 120.1(6) . 2_577 ?
C9B C10B C1B 117.6(6) . . ?
C9B C10B C2B 122.3(7) . 2_577 ?

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
C1A C2A C3A F2A 178.5(8) . . . . ?
C1A C2A C3A C4A -0.9(13) . . . . ?
I1A C1A C2A C3A -178.8(6) . . . . ?
I1A C1A C2A F1A 0.8(11) . . . . ?
I1A C1A C6A F4A -1.0(11) . . . . ?
I1A C1A C6A C5A 178.7(7) . . . . ?
F2A C3A C4A I3A -0.8(11) . . . . ?
F2A C3A C4A C5A -178.2(8) . . . . ?
C2A C1A C6A F4A 179.6(8) . . . . ?
C2A C1A C6A C5A -0.7(13) . . . . ?
C2A C3A C4A I3A 178.5(6) . . . . ?
C2A C3A C4A C5A 1.1(13) . . . . ?
I3A C4A C5A F3A 3.9(12) . . . . ?
I3A C4A C5A C6A -178.6(7) . . . . ?
F3A C5A C6A C1A 178.6(8) . . . . ?
F3A C5A C6A F4A -1.7(13) . . . . ?
C3A C4A C5A F3A -178.7(8) . . . . ?
C3A C4A C5A C6A -1.2(13) . . . . ?
C4A C5A C6A C1A 1.0(14) . . . . ?
C4A C5A C6A F4A -179.3(8) . . . . ?
C6A C1A C2A C3A 0.6(13) . . . . ?
C6A C1A C2A F1A -179.8(8) . . . . ?
F1A C2A C3A F2A -1.1(13) . . . . ?
F1A C2A C3A C4A 179.5(8) . . . . ?
C1B C2B C3B C4B -0.1(11) . . . . ?
C1B C6B C7B C8B 0.0(12) . . . . ?
C2B C1B C6B C5B -1.1(9) . . . . ?
C2B C1B C6B C7B -179.1(6) . . . . ?
C2B C1B C10B C2B -2.4(10) . . . 2_577 ?
C2B C1B C10B C9B 179.2(6) . . . . ?
C2B C3B C4B C5B -1.7(13) . . . . ?
C3B C4B C5B C6B 2.0(13) . . . . ?
C4B C5B C6B C1B -0.7(11) . . . . ?
C4B C5B C6B C7B 177.3(8) . . . . ?
C5B C6B C7B C8B -177.9(8) . . . . ?
C6B C1B C2B C3B 1.4(9) . . . . ?
C6B C1B C2B C10B -178.6(6) . . . 2_577 ?
C6B C1B C10B C2B 178.6(6) . . . 2_577 ?
C6B C1B C10B C9B 0.2(9) . . . . ?
C6B C7B C8B C9B -0.2(14) . . . . ?
C7B C8B C9B C10B 0.3(13) . . . . ?
C8B C9B C10B C1B -0.3(10) . . . . ?
C8B C9B C10B C2B -178.7(7) . . . 2_577 ?
C10B C1B C2B C3B -177.7(6) . . . . ?
C10B C1B C2B C10B 2.4(10) . . . 2_577 ?
C10B C1B C6B C5B 178.0(6) . . . . ?
C10B C1B C6B C7B 0.0(10) . . . . ?
C10B C2B C3B C4B 179.9(7) 2_577 . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DCM'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_benzanthra_14tfib_auto_gaussian
_database_code_depnum_ccdc_archive 'CCDC 2281269'
loop_
_audit_author_name
_audit_author_address
'Jogirdas Vainauskas'
;McGill University, University of Birmingham
Canada
;
_audit_update_record             
;
2023-07-13 deposited with the CCDC.	2023-10-09 downloaded from the CCDC.
;
_audit_creation_date             2023-07-13
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
# start Validation Reply Form
_vrf_PLAT342_benzanthra_14tfib_auto_gaussian 
;
PROBLEM: Low Bond Precision on C-C Bonds ............... 0.02386 Ang.
RESPONSE: This is most likely due to thermal motion, arising from
data collection at room temperature.
;
# end Validation Reply Form
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H12, 2.5(C6 F4 I2)'
_chemical_formula_sum            'C33 H12 F10 I5'
_chemical_formula_weight         1232.93
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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'

_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                   6.1683(5)
_cell_length_b                   15.3618(13)
_cell_length_c                   18.5460(13)
_cell_angle_alpha                94.961(6)
_cell_angle_beta                 93.811(6)
_cell_angle_gamma                97.532(7)
_cell_volume                     1730.3(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2904
_cell_measurement_temperature    291.9(4)
_cell_measurement_theta_max      71.7970
_cell_measurement_theta_min      3.8720
_shelx_estimated_absorpt_T_max   0.221
_shelx_estimated_absorpt_T_min   0.064
_exptl_absorpt_coefficient_mu    36.001
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.815
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.81a (Rigaku Oxford Diffraction, 2023)
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
_exptl_crystal_density_diffrn    2.366
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       lath
_exptl_crystal_F_000             1130
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 -1 0.0570
-3 4 -8 0.0570
-3 -4 -2 0.0634
0 0 -12 0.0371
0 0 -12 0.0352
3 6 -6 0.0925
-2 -6 -5 0.0543
3 6 -3 0.0957
-3 -5 5 0.0694
3 3 -6 0.0932
0 -7 -8 0.0285
2 -3 -10 0.0680
-3 2 8 0.0472
-3 6 4 0.0421
0 -10 -2 0.0383
4 -2 -4 0.0941
0 0 12 0.0209
0 9 4 0.0757
3 -3 5 0.0744
1 -9 7 0.0453

_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
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 1.0006 -1.0011 -0.0875 -0.0465 0.0768
-2.5835 4.0663 -8.1214 -0.8649 -0.4706 -0.1745
-3.3727 -3.5889 -1.8344 -0.3621 -0.1983 -0.9108
-0.1571 0.3445 -11.9445 -0.9719 0.2327 0.0346
0.1528 -0.4523 -11.9209 -0.9422 0.3331 0.0359
2.6079 5.7683 -5.5620 -0.3014 0.1078 0.9474
-2.2535 -5.6507 -4.9677 -0.5189 0.1823 -0.8352
2.8228 5.9479 -3.0620 -0.0868 0.0681 0.9939
-2.8963 -5.0207 5.2861 0.2533 -0.1956 -0.9474
3.1234 3.3272 -6.4541 -0.3187 0.3744 0.8708
-0.0291 -6.9634 -7.6534 -0.5663 0.6613 -0.4919
2.0715 -2.9405 -10.0075 -0.6340 0.7419 0.2183
-3.0516 1.9974 8.1377 0.4208 -0.7752 -0.4712
-3.0098 6.4640 4.2291 0.0783 -0.9894 -0.1219
0.0773 -9.6414 -1.6533 -0.0582 0.7233 -0.6881
3.8117 -1.7598 -4.3082 -0.0611 0.7797 0.6231
0.1527 -0.3561 11.9469 0.9719 -0.2326 -0.0363
0.0221 8.7805 4.4436 0.2953 -0.7140 0.6348
3.4375 -2.9740 5.2363 0.6866 0.5864 0.4297
0.6493 -8.7232 6.6295 0.6405 0.5486 -0.5373

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0497
_diffrn_reflns_av_unetI/netI     0.0642
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            14023
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.640
_diffrn_reflns_theta_min         3.951
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      291.9(4)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3537
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -111.00 -74.00   1.00    1.79    --  -41.27-140.00 134.00   37
  2  ω    -59.00 -33.00   1.00    1.79    --  -41.27 140.00-166.00   26
  3  ω    -80.00 -38.00   1.00    1.79    --  -41.27 130.00  19.00   42
  4  ω     65.00  90.00   1.00    1.79    --   41.27-130.00 -52.00   25
  5  ω     46.00  71.00   1.00    1.79    --   41.27-140.00 134.00   25
  6  ω     61.00 124.00   1.00    7.16    --  102.80-140.00 134.00   63
  7  ω     61.00 111.00   1.00    7.16    --  102.80-130.00 -52.00   50
  8  ω     91.00 120.00   1.00    7.16    --  102.80 140.00-166.00   29
  9  ω    110.00 136.00   1.00    7.16    --  102.80 130.00  19.00   26
 10  ω   -120.00   0.00   1.00    1.79    --  -41.27 -19.00  90.00  120
 11  ω   -109.00 -18.00   1.00    1.79    --  -41.27 -38.00   0.00   91
 12  ω     28.00  89.00   1.00    1.79    --   41.27-125.00 -30.00   61
 13  ω     45.00 114.00   1.00    7.16    --  102.80 -45.00 -90.00   69
 14  ω    103.00 163.00   1.00    7.16    --  102.80  77.00  30.00   60
 15  ω    106.00 177.00   1.00    7.16    --  102.80  77.00-120.00   71
 16  ω     39.00  74.00   1.00    7.16    --  102.80-111.00-150.00   35
 17  ω     64.00 103.00   1.00    7.16    --  102.80 -94.00 -30.00   39
 18  ω    116.00 176.00   1.00    7.16    --  102.80 111.00 -30.00   60
 19  ω     81.00 106.00   1.00    7.16    --  102.80-111.00-150.00   25
 20  ω    103.00 136.00   1.00    7.16    --  102.80  77.00   0.00   33
 21  ω    145.00 173.00   1.00    7.16    --  102.80  77.00   0.00   28
 22  ω     40.00  65.00   1.00    7.16    --  102.80 -77.00  30.00   25
 23  ω    104.00 174.00   1.00    7.16    --  102.80 111.00  60.00   70
 24  ω    115.00 167.00   1.00    7.16    --  102.80 111.00 -90.00   52
 25  ω     59.00 108.00   1.00    7.16    --  102.80-111.00 150.00   49
 26  ω     93.00 168.00   1.00    7.16    --  102.80  30.00 -30.00   75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0713471000
_diffrn_orient_matrix_UB_12      -0.0071477000
_diffrn_orient_matrix_UB_13      0.0802252000
_diffrn_orient_matrix_UB_21      0.1458550000
_diffrn_orient_matrix_UB_22      -0.0698352000
_diffrn_orient_matrix_UB_23      -0.0234190000
_diffrn_orient_matrix_UB_31      0.1936506000
_diffrn_orient_matrix_UB_32      0.0734885000
_diffrn_orient_matrix_UB_33      -0.0033208000
_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              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3422
_reflns_number_total             6690
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         2.130
_refine_diff_density_min         -1.635
_refine_diff_density_rms         0.185
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     421
_refine_ls_number_reflns         6690
_refine_ls_number_restraints     348
_refine_ls_R_factor_all          0.1268
_refine_ls_R_factor_gt           0.0750
_refine_ls_restrained_S_all      1.026
_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)+(0.1183P)²+2.5413P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2011
_refine_ls_wR_factor_ref         0.2656
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Aromatic/amide H refined with riding coordinates:
 C1A(H1A), C7A(H7A), C14A(H14A), C2A(H2A), C4A(H4A), C5A(H5A), C9A(H9A),
 C10A(H10A), C11A(H11A), C12A(H12A), C17A(H17A), C18A(H18A)
3.b Fitted hexagon refined as free rotating group:
 C15A(C6A,C7A,C8A,C13A,C14A)
;
_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
C1A C 0.419(4) 0.5865(13) 0.4105(12) 0.112(5) Uani 1 1 d . . . . .
H1A H 0.405264 0.638870 0.437947 0.135 Uiso 1 1 calc R U . . .
F1B F 0.9526(19) 0.2688(7) 0.5207(7) 0.116(4) Uani 1 1 d . . . . .
I1B I 1.3504(2) 0.19768(9) 0.44254(6) 0.0997(4) Uani 1 1 d . . . . .
F2B F 0.7110(18) 0.2089(7) 0.6247(7) 0.116(4) Uani 1 1 d . . . . .
I2B I 0.72893(18) 0.04310(7) 0.71607(6) 0.0865(4) Uani 1 1 d . . . . .
F3B F 1.1283(17) -0.0258(7) 0.6391(7) 0.112(4) Uani 1 1 d . . . . .
F4B F 1.3639(19) 0.0353(8) 0.5361(8) 0.138(5) Uani 1 1 d . . . . .
C1B C 1.162(2) 0.1507(10) 0.5261(8) 0.071(3) Uani 1 1 d . . . . .
C2B C 0.998(2) 0.1958(9) 0.5496(7) 0.064(3) Uani 1 1 d . . . . .
C3B C 0.874(2) 0.1623(10) 0.6036(8) 0.069(3) Uani 1 1 d . . . . .
C4B C 0.914(2) 0.0892(8) 0.6347(7) 0.060(3) Uani 1 1 d . . . . .
C5B C 1.079(2) 0.0481(9) 0.6090(9) 0.072(3) Uani 1 1 d . . . . .
C6B C 1.199(2) 0.0793(9) 0.5543(9) 0.071(3) Uani 1 1 d . . . . .
I1C I 0.7083(2) 0.41886(9) 0.14023(6) 0.1043(5) Uani 1 1 d . . . . .
F1C F 1.1228(16) 0.3608(7) 0.0641(6) 0.103(3) Uani 1 1 d . . . . .
F2C F 0.6577(15) 0.5771(7) 0.0424(6) 0.101(3) Uani 1 1 d . . . . .
C1C C 1.059(2) 0.4304(9) 0.0329(8) 0.071(3) Uani 1 1 d . . . . .
C2C C 0.882(2) 0.4675(9) 0.0561(7) 0.068(3) Uani 1 1 d . . . . .
C3C C 0.827(2) 0.5375(10) 0.0224(8) 0.074(3) Uani 1 1 d . . . . .
C15A C 0.503(2) 0.3353(6) 0.2956(6) 0.102(4) Uani 1 1 d G . . . .
C6A C 0.692(2) 0.3026(8) 0.3196(5) 0.095(4) Uani 1 1 d G . . . .
C7A C 0.7415(18) 0.2232(9) 0.2874(7) 0.124(5) Uani 1 1 d G . . . .
H7A H 0.867911 0.201353 0.303496 0.149 Uiso 1 1 calc R U . . .
C8A C 0.602(3) 0.1765(6) 0.2312(7) 0.109(5) Uani 1 1 d G . . . .
C13A C 0.413(2) 0.2092(8) 0.2071(5) 0.113(5) Uani 1 1 d G . . . .
C14A C 0.3636(17) 0.2886(9) 0.2394(7) 0.116(5) Uani 1 1 d G . . . .
H14A H 0.237159 0.310452 0.223299 0.139 Uiso 1 1 calc R U . . .
I1D I 0.2935(2) 0.83802(9) -0.00590(6) 0.1044(5) Uani 1 1 d . . . . .
I2D I -0.31656(18) 0.68370(8) 0.27056(6) 0.0879(4) Uani 1 1 d . . . . .
F1D F -0.1118(17) 0.9063(7) 0.0706(6) 0.107(3) Uani 1 1 d . . . . .
F2D F -0.3447(16) 0.8460(6) 0.1760(6) 0.098(3) Uani 1 1 d . . . . .
F3D F 0.0965(16) 0.6198(6) 0.1973(6) 0.092(3) Uani 1 1 d . . . . .
F4D F 0.3297(15) 0.6799(7) 0.0928(6) 0.100(3) Uani 1 1 d . . . . .
C1D C 0.115(2) 0.7928(10) 0.0781(7) 0.070(3) Uani 1 1 d . . . . .
C2D C -0.058(2) 0.8341(10) 0.1024(9) 0.078(4) Uani 1 1 d . . . . .
C3D C -0.182(2) 0.8036(10) 0.1554(9) 0.073(3) Uani 1 1 d . . . . .
C4D C -0.133(2) 0.7342(10) 0.1894(7) 0.067(3) Uani 1 1 d . . . . .
C5D C 0.040(2) 0.6928(9) 0.1673(8) 0.068(3) Uani 1 1 d . . . . .
C6D C 0.163(2) 0.7227(10) 0.1109(8) 0.068(3) Uani 1 1 d . . . . .
C2A C 0.602(4) 0.5421(12) 0.4256(13) 0.114(5) Uani 1 1 d . . . . .
H2A H 0.715736 0.564554 0.460531 0.137 Uiso 1 1 calc R U . . .
C3A C 0.599(4) 0.4630(13) 0.3840(12) 0.106(4) Uani 1 1 d . . . . .
C4A C 0.775(4) 0.4284(16) 0.4053(14) 0.129(6) Uani 1 1 d . . . . .
H4A H 0.869761 0.459222 0.442770 0.155 Uiso 1 1 calc R U . . .
C5A C 0.830(5) 0.3427(16) 0.3725(14) 0.135(7) Uani 1 1 d . . . . .
H5A H 0.954505 0.319311 0.388480 0.162 Uiso 1 1 calc R U . . .
C9A C 0.643(4) 0.0901(13) 0.1941(11) 0.109(5) Uani 1 1 d . . . . .
H9A H 0.765397 0.063322 0.205811 0.131 Uiso 1 1 calc R U . . .
C10A C 0.478(4) 0.0536(14) 0.1401(12) 0.120(6) Uani 1 1 d . . . . .
H10A H 0.493604 -0.000618 0.115986 0.143 Uiso 1 1 calc R U . . .
C11A C 0.306(5) 0.089(2) 0.1208(17) 0.149(8) Uani 1 1 d . . . . .
H11A H 0.208279 0.061237 0.082953 0.179 Uiso 1 1 calc R U . . .
C12A C 0.265(4) 0.1678(15) 0.1550(13) 0.126(6) Uani 1 1 d . . . . .
H12A H 0.138232 0.191563 0.142434 0.152 Uiso 1 1 calc R U . . .
C16A C 0.450(4) 0.4250(14) 0.3299(12) 0.113(5) Uani 1 1 d . . . . .
C17A C 0.284(4) 0.4616(15) 0.3128(11) 0.115(5) Uani 1 1 d . . . . .
H17A H 0.181581 0.434319 0.276040 0.138 Uiso 1 1 calc R U . . .
C18A C 0.251(4) 0.5503(15) 0.3519(13) 0.125(6) Uani 1 1 d . . . . .
H18A H 0.132103 0.579214 0.339426 0.151 Uiso 1 1 calc R U . . .


_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
C1A H1A 0.9300 . ?
C1A C2A 1.42(3) . ?
C1A C18A 1.47(3) . ?
F1B C2B 1.338(16) . ?
I1B C1B 2.116(13) . ?
F2B C3B 1.370(16) . ?
I2B C4B 2.071(10) . ?
F3B C5B 1.368(17) . ?
F4B C6B 1.336(16) . ?
C1B C2B 1.374(19) . ?
C1B C6B 1.29(2) . ?
C2B C3B 1.394(16) . ?
C3B C4B 1.349(19) . ?
C4B C5B 1.354(19) . ?
C5B C6B 1.381(18) . ?
I1C C2C 2.086(11) . ?
F1C C1C 1.350(18) . ?
F2C C3C 1.332(17) . ?
C1C C2C 1.37(2) . ?
C1C C3C 1.373(18) 2_765 ?
C2C C3C 1.36(2) . ?
C15A C6A 1.3900 . ?
C15A C14A 1.3900 . ?
C15A C16A 1.55(2) . ?
C6A C7A 1.3900 . ?
C6A C5A 1.31(3) . ?
C7A H7A 0.9300 . ?
C7A C8A 1.3900 . ?
C8A C13A 1.3900 . ?
C8A C9A 1.50(2) . ?
C13A C14A 1.3900 . ?
C13A C12A 1.34(3) . ?
C14A H14A 0.9300 . ?
I1D C1D 2.083(12) . ?
I2D C4D 2.083(12) . ?
F1D C2D 1.369(19) . ?
F2D C3D 1.326(17) . ?
F3D C5D 1.370(18) . ?
F4D C6D 1.335(17) . ?
C1D C2D 1.39(2) . ?
C1D C6D 1.34(2) . ?
C2D C3D 1.361(19) . ?
C3D C4D 1.34(2) . ?
C4D C5D 1.38(2) . ?
C5D C6D 1.408(17) . ?
C2A H2A 0.9300 . ?
C2A C3A 1.38(3) . ?
C3A C4A 1.32(3) . ?
C3A C16A 1.35(3) . ?
C4A H4A 0.9300 . ?
C4A C5A 1.49(3) . ?
C5A H5A 0.9300 . ?
C9A H9A 0.9300 . ?
C9A C10A 1.40(3) . ?
C10A H10A 0.9300 . ?
C10A C11A 1.30(4) . ?
C11A H11A 0.9300 . ?
C11A C12A 1.37(4) . ?
C12A H12A 0.9300 . ?
C16A C17A 1.26(3) . ?
C17A H17A 0.9300 . ?
C17A C18A 1.53(3) . ?
C18A H18A 0.9300 . ?

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
C2A C1A H1A 119.8 . . ?
C2A C1A C18A 120(2) . . ?
C18A C1A H1A 119.8 . . ?
C2B C1B I1B 119.5(11) . . ?
C6B C1B I1B 120.5(10) . . ?
C6B C1B C2B 120.1(12) . . ?
F1B C2B C1B 121.7(11) . . ?
F1B C2B C3B 120.1(12) . . ?
C1B C2B C3B 118.1(13) . . ?
F2B C3B C2B 116.1(12) . . ?
C4B C3B F2B 121.4(11) . . ?
C4B C3B C2B 122.5(12) . . ?
C3B C4B I2B 121.0(9) . . ?
C3B C4B C5B 116.3(11) . . ?
C5B C4B I2B 122.7(10) . . ?
F3B C5B C6B 119.2(13) . . ?
C4B C5B F3B 118.9(12) . . ?
C4B C5B C6B 122.0(13) . . ?
F4B C6B C5B 116.2(14) . . ?
C1B C6B F4B 122.6(12) . . ?
C1B C6B C5B 121.1(13) . . ?
F1C C1C C2C 120.2(12) . . ?
F1C C1C C3C 118.7(15) . 2_765 ?
C3C C1C C2C 121.1(15) 2_765 . ?
C1C C2C I1C 121.1(12) . . ?
C3C C2C I1C 121.8(11) . . ?
C3C C2C C1C 117.0(12) . . ?
F2C C3C C1C 117.9(16) . 2_765 ?
F2C C3C C2C 120.3(12) . . ?
C2C C3C C1C 121.8(14) . 2_765 ?
C6A C15A C14A 120.0 . . ?
C6A C15A C16A 120.3(14) . . ?
C14A C15A C16A 119.7(14) . . ?
C15A C6A C7A 120.0 . . ?
C5A C6A C15A 123.4(16) . . ?
C5A C6A C7A 116.6(16) . . ?
C6A C7A H7A 120.0 . . ?
C6A C7A C8A 120.0 . . ?
C8A C7A H7A 120.0 . . ?
C7A C8A C9A 123.2(15) . . ?
C13A C8A C7A 120.0 . . ?
C13A C8A C9A 116.8(15) . . ?
C8A C13A C14A 120.0 . . ?
C12A C13A C8A 124.5(17) . . ?
C12A C13A C14A 115.5(17) . . ?
C15A C14A H14A 120.0 . . ?
C13A C14A C15A 120.0 . . ?
C13A C14A H14A 120.0 . . ?
C2D C1D I1D 121.6(11) . . ?
C6D C1D I1D 120.9(11) . . ?
C6D C1D C2D 117.5(12) . . ?
F1D C2D C1D 119.2(12) . . ?
C3D C2D F1D 118.3(14) . . ?
C3D C2D C1D 122.4(15) . . ?
F2D C3D C2D 119.4(14) . . ?
F2D C3D C4D 119.9(12) . . ?
C4D C3D C2D 120.7(14) . . ?
C3D C4D I2D 122.7(11) . . ?
C3D C4D C5D 118.1(12) . . ?
C5D C4D I2D 119.1(11) . . ?
F3D C5D C4D 122.1(11) . . ?
F3D C5D C6D 116.7(13) . . ?
C4D C5D C6D 121.1(14) . . ?
F4D C6D C1D 122.1(12) . . ?
F4D C6D C5D 117.8(14) . . ?
C1D C6D C5D 120.1(13) . . ?
C1A C2A H2A 122.8 . . ?
C3A C2A C1A 114(2) . . ?
C3A C2A H2A 122.8 . . ?
C4A C3A C2A 108(3) . . ?
C4A C3A C16A 124(3) . . ?
C16A C3A C2A 129(2) . . ?
C3A C4A H4A 118.2 . . ?
C3A C4A C5A 124(3) . . ?
C5A C4A H4A 118.2 . . ?
C6A C5A C4A 116(2) . . ?
C6A C5A H5A 122.2 . . ?
C4A C5A H5A 122.2 . . ?
C8A C9A H9A 123.2 . . ?
C10A C9A C8A 114(2) . . ?
C10A C9A H9A 123.2 . . ?
C9A C10A H10A 117.3 . . ?
C11A C10A C9A 125(3) . . ?
C11A C10A H10A 117.3 . . ?
C10A C11A H11A 119.3 . . ?
C10A C11A C12A 121(3) . . ?
C12A C11A H11A 119.3 . . ?
C13A C12A C11A 118(3) . . ?
C13A C12A H12A 120.9 . . ?
C11A C12A H12A 120.9 . . ?
C3A C16A C15A 113(2) . . ?
C17A C16A C15A 126(3) . . ?
C17A C16A C3A 120(3) . . ?
C16A C17A H17A 119.6 . . ?
C16A C17A C18A 121(2) . . ?
C18A C17A H17A 119.6 . . ?
C1A C18A C17A 115(2) . . ?
C1A C18A H18A 122.4 . . ?
C17A C18A H18A 122.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1A C2A C3A C4A -178.3(15) . . . . ?
C1A C2A C3A C16A 3(3) . . . . ?
F1B C2B C3B F2B -1(2) . . . . ?
F1B C2B C3B C4B -179.7(15) . . . . ?
I1B C1B C2B F1B 0(2) . . . . ?
I1B C1B C2B C3B 178.7(11) . . . . ?
I1B C1B C6B F4B 4(2) . . . . ?
I1B C1B C6B C5B 179.7(12) . . . . ?
F2B C3B C4B I2B 0(2) . . . . ?
F2B C3B C4B C5B 179.4(15) . . . . ?
I2B C4B C5B F3B -2(2) . . . . ?
I2B C4B C5B C6B 179.4(12) . . . . ?
F3B C5B C6B F4B -2(2) . . . . ?
F3B C5B C6B C1B -177.7(16) . . . . ?
C1B C2B C3B F2B -179.2(15) . . . . ?
C1B C2B C3B C4B 2(2) . . . . ?
C2B C1B C6B F4B -176.5(16) . . . . ?
C2B C1B C6B C5B -1(3) . . . . ?
C2B C3B C4B I2B 179.0(12) . . . . ?
C2B C3B C4B C5B -2(2) . . . . ?
C3B C4B C5B F3B 179.3(14) . . . . ?
C3B C4B C5B C6B 0(2) . . . . ?
C4B C5B C6B F4B 176.9(16) . . . . ?
C4B C5B C6B C1B 1(3) . . . . ?
C6B C1B C2B F1B -178.7(16) . . . . ?
C6B C1B C2B C3B 0(2) . . . . ?
I1C C2C C3C F2C 0(2) . . . . ?
I1C C2C C3C C1C 180.0(10) . . . 2_765 ?
F1C C1C C2C I1C 0.7(18) . . . . ?
F1C C1C C2C C3C 179.8(13) . . . . ?
C1C C2C C3C F2C -179.5(13) . . . . ?
C1C C2C C3C C1C 1(2) . . . 2_765 ?
C3C C1C C2C I1C -180.0(10) 2_765 . . . ?
C3C C1C C2C C3C -1(2) 2_765 . . . ?
C15A C6A C7A C8A 0.0 . . . . ?
C15A C6A C5A C4A -1(3) . . . . ?
C15A C16A C17A C18A 179.3(12) . . . . ?
C6A C15A C14A C13A 0.0 . . . . ?
C6A C15A C16A C3A -1.8(15) . . . . ?
C6A C15A C16A C17A 179.9(13) . . . . ?
C6A C7A C8A C13A 0.0 . . . . ?
C6A C7A C8A C9A -179.4(10) . . . . ?
C7A C6A C5A C4A 179.1(14) . . . . ?
C7A C8A C13A C14A 0.0 . . . . ?
C7A C8A C13A C12A -177.7(13) . . . . ?
C7A C8A C9A C10A 178.5(10) . . . . ?
C8A C13A C14A C15A 0.0 . . . . ?
C8A C13A C12A C11A -3(2) . . . . ?
C8A C9A C10A C11A 1(3) . . . . ?
C13A C8A C9A C10A -0.9(15) . . . . ?
C14A C15A C6A C7A 0.0 . . . . ?
C14A C15A C6A C5A -179.7(17) . . . . ?
C14A C15A C16A C3A 179.9(10) . . . . ?
C14A C15A C16A C17A 1.5(19) . . . . ?
C14A C13A C12A C11A 179.5(15) . . . . ?
I1D C1D C2D F1D 0(2) . . . . ?
I1D C1D C2D C3D 177.5(12) . . . . ?
I1D C1D C6D F4D 2(2) . . . . ?
I1D C1D C6D C5D -179.6(10) . . . . ?
I2D C4D C5D F3D -0.4(18) . . . . ?
I2D C4D C5D C6D 177.7(10) . . . . ?
F1D C2D C3D F2D -2(2) . . . . ?
F1D C2D C3D C4D -178.6(15) . . . . ?
F2D C3D C4D I2D 4(2) . . . . ?
F2D C3D C4D C5D -178.8(14) . . . . ?
F3D C5D C6D F4D -2.3(19) . . . . ?
F3D C5D C6D C1D 178.9(13) . . . . ?
C1D C2D C3D F2D -180.0(15) . . . . ?
C1D C2D C3D C4D 4(3) . . . . ?
C2D C1D C6D F4D -178.3(14) . . . . ?
C2D C1D C6D C5D 0(2) . . . . ?
C2D C3D C4D I2D -179.7(12) . . . . ?
C2D C3D C4D C5D -2(2) . . . . ?
C3D C4D C5D F3D -177.8(13) . . . . ?
C3D C4D C5D C6D 0(2) . . . . ?
C4D C5D C6D F4D 179.5(13) . . . . ?
C4D C5D C6D C1D 1(2) . . . . ?
C6D C1D C2D F1D 179.7(14) . . . . ?
C6D C1D C2D C3D -3(2) . . . . ?
C2A C1A C18A C17A 3(2) . . . . ?
C2A C3A C4A C5A -179.4(18) . . . . ?
C2A C3A C16A C15A 179.7(14) . . . . ?
C2A C3A C16A C17A -2(3) . . . . ?
C3A C4A C5A C6A 0(3) . . . . ?
C3A C16A C17A C18A 1(3) . . . . ?
C4A C3A C16A C15A 1(2) . . . . ?
C4A C3A C16A C17A 179.5(16) . . . . ?
C5A C6A C7A C8A 179.7(15) . . . . ?
C9A C8A C13A C14A 179.5(9) . . . . ?
C9A C8A C13A C12A 1.7(13) . . . . ?
C9A C10A C11A C12A -2(4) . . . . ?
C10A C11A C12A C13A 3(3) . . . . ?
C12A C13A C14A C15A 177.9(11) . . . . ?
C16A C15A C6A C7A -178.4(9) . . . . ?
C16A C15A C6A C5A 1.9(17) . . . . ?
C16A C15A C14A C13A 178.4(9) . . . . ?
C16A C3A C4A C5A -1(3) . . . . ?
C16A C17A C18A C1A -2(2) . . . . ?
C18A C1A C2A C3A -3(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.854
_oxdiff_exptl_absorpt_empirical_full_min 0.570
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DCM'
_exptl_crystal_preparation       Luminescent
