# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_azu_14tfib_2-3_150K
_database_code_depnum_ccdc_archive 'CCDC 2000772'
loop_
_audit_author_name
_audit_author_address
'Filip Topic'
;McGill University
Canada
;
_audit_update_record             
;
2020-05-03 deposited with the CCDC.	2020-11-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_formula_moiety         '3(C6 F4 I2), 2(C10 H8)'
_chemical_formula_sum            'C38 H16 F12 I6'
_chemical_formula_weight         1461.91

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   5.9321(6)
_cell_length_b                   11.9878(13)
_cell_length_c                   14.8586(16)
_cell_angle_alpha                73.9545(12)
_cell_angle_beta                 80.1893(13)
_cell_angle_gamma                84.8797(12)
_cell_volume                     999.63(18)
_cell_formula_units_Z            1
_cell_measurement_temperature    150.0(1)
_cell_measurement_reflns_used    4818
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      28.43

_exptl_crystal_description       block
_exptl_crystal_colour            'dark blue'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.428
_exptl_crystal_F_000             670
_exptl_crystal_size_max          0.534
_exptl_crystal_size_mid          0.173
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    4.746
_shelx_estimated_absorpt_T_min   0.186
_shelx_estimated_absorpt_T_max   0.797
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2839
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;

_diffrn_ambient_temperature      150.0(1)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Incoatec Microfocus X-ray Source I\mS (Mo)'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-DUO, Dual, APEX-II'
_diffrn_detector                 CCD
_diffrn_detector_type            APEX-II
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            9931
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_av_R_equivalents  0.0191
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.443
_diffrn_reflns_theta_max         28.861
_diffrn_reflns_theta_full        25.250
_diffrn_measured_fraction_theta_max 0.906
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.906
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.906
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4740
_reflns_number_gt                3970
_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       'Bruker APEX3'
_computing_cell_refinement       'Bruker APEX3'
_computing_data_reduction        'Bruker APEX3'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_publication_material  
'OLEX2 (Dolomanov et al., 2009) & WinGX (Farrugia, 2012)'

_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)+(0.0283P)²+0.4982P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4740
_refine_ls_number_parameters     253
_refine_ls_number_restraints     34
_refine_ls_R_factor_all          0.0328
_refine_ls_R_factor_gt           0.0251
_refine_ls_wR_factor_ref         0.0637
_refine_ls_wR_factor_gt          0.0595
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.001
_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 1.1673(5) 0.0022(3) 0.1841(2) 0.0298(7) Uani 1 1 d D . . . .
H1A H 1.302892 0.012386 0.138836 0.036 Uiso 1 1 calc R U . . .
C2A C 0.9861(5) -0.0668(2) 0.1865(2) 0.0346(8) Uani 1 1 d D . . . .
H2A H 0.979351 -0.110063 0.142364 0.042 Uiso 1 1 calc R U . . .
C3A C 0.8166(5) -0.0622(3) 0.2638(2) 0.0322(7) Uani 1 1 d D . . . .
H3A H 0.677949 -0.102200 0.280842 0.039 Uiso 1 1 calc R U . . .
C4A C 0.8859(5) 0.0110(2) 0.3117(2) 0.0263(6) Uani 1 1 d D . . . .
C5A C 0.7660(5) 0.0382(3) 0.3914(2) 0.0307(7) Uani 1 1 d D . . . .
H5A H 0.624099 0.001944 0.415784 0.037 Uiso 1 1 calc R U . . .
C6A C 0.8238(5) 0.1104(3) 0.4404(2) 0.0315(7) Uani 1 1 d D . . . .
H6A H 0.712390 0.119992 0.492132 0.038 Uiso 1 1 calc R U . . .
C7A C 1.0224(5) 0.1720(3) 0.4256(2) 0.0289(7) Uani 1 1 d D . . . .
H7A H 1.029320 0.214532 0.470301 0.035 Uiso 1 1 calc R U . . .
C8A C 1.2097(5) 0.1798(3) 0.3551(2) 0.0301(7) Uani 1 1 d D . . . .
H8A H 1.326456 0.227655 0.357625 0.036 Uiso 1 1 calc R U . . .
C9A C 1.2515(5) 0.1272(2) 0.2806(2) 0.0291(7) Uani 1 1 d D . . . .
H9A H 1.392105 0.144507 0.239227 0.035 Uiso 1 1 calc R U . . .
C10A C 1.1149(5) 0.0532(2) 0.2592(2) 0.0253(6) Uani 1 1 d D . . . .
C1S C 0.6130(5) 0.5253(2) 0.1726(2) 0.0225(6) Uani 1 1 d . . . . .
C2S C 0.4405(5) 0.4951(3) 0.1321(2) 0.0247(6) Uani 1 1 d . . . . .
C3S C 0.3212(5) 0.5797(3) 0.0705(2) 0.0261(6) Uani 1 1 d . . . . .
C4S C 0.3714(5) 0.6952(3) 0.0475(2) 0.0259(6) Uani 1 1 d . . . . .
C5S C 0.5435(5) 0.7246(3) 0.0883(2) 0.0261(6) Uani 1 1 d . . . . .
C6S C 0.6600(5) 0.6409(3) 0.1494(2) 0.0256(6) Uani 1 1 d . . . . .
F1S F 0.3879(3) 0.38407(15) 0.15077(15) 0.0367(5) Uani 1 1 d . . . . .
F2S F 0.1573(3) 0.54516(18) 0.03381(15) 0.0394(5) Uani 1 1 d . . . . .
F3S F 0.5959(3) 0.83637(16) 0.06965(16) 0.0408(5) Uani 1 1 d . . . . .
F4S F 0.8250(3) 0.67486(17) 0.18732(15) 0.0394(5) Uani 1 1 d . . . . .
I1S I 0.79336(3) 0.39869(2) 0.26275(2) 0.03240(7) Uani 1 1 d . . . . .
I2S I 0.19602(4) 0.82031(2) -0.04644(2) 0.03691(7) Uani 1 1 d . . . . .
C1T C 0.6155(5) 0.4132(2) 0.5635(2) 0.0214(6) Uani 1 1 d . . . . .
C2T C 0.4420(5) 0.3866(2) 0.5217(2) 0.0231(6) Uani 1 1 d . . . . .
C3T C 0.3311(5) 0.4714(3) 0.4592(2) 0.0248(6) Uani 1 1 d . . . . .
F1T F 0.1653(3) 0.43977(16) 0.42109(15) 0.0373(5) Uani 1 1 d . . . . .
F2T F 0.3838(3) 0.27575(15) 0.54006(15) 0.0356(5) Uani 1 1 d . . . . .
I1T I 0.78506(3) 0.28464(2) 0.65717(2) 0.02791(6) 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 C10A 1.393(4) . ?
C1A C2A 1.403(4) . ?
C1A H1A 0.9500 . ?
C2A C3A 1.402(4) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.398(4) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.379(4) . ?
C4A C10A 1.501(4) . ?
C5A C6A 1.373(4) . ?
C5A H5A 0.9500 . ?
C6A C7A 1.399(4) . ?
C6A H6A 0.9500 . ?
C7A C8A 1.382(4) . ?
C7A H7A 0.9500 . ?
C8A C9A 1.394(4) . ?
C8A H8A 0.9500 . ?
C9A C10A 1.386(3) . ?
C9A H9A 0.9500 . ?
C1S C6S 1.374(4) . ?
C1S C2S 1.391(4) . ?
C1S I1S 2.078(3) . ?
C2S F1S 1.337(3) . ?
C2S C3S 1.395(4) . ?
C3S F2S 1.339(3) . ?
C3S C4S 1.379(4) . ?
C4S C5S 1.388(4) . ?
C4S I2S 2.083(3) . ?
C5S F3S 1.345(3) . ?
C5S C6S 1.376(4) . ?
C6S F4S 1.352(3) . ?
C1T C3T 1.383(4) 2_666 ?
C1T C2T 1.390(4) . ?
C1T I1T 2.083(3) . ?
C2T F2T 1.344(3) . ?
C2T C3T 1.377(4) . ?
C3T F1T 1.344(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
C10A C1A C2A 108.6(3) . . ?
C10A C1A H1A 125.7 . . ?
C2A C1A H1A 125.7 . . ?
C3A C2A C1A 109.8(3) . . ?
C3A C2A H2A 125.1 . . ?
C1A C2A H2A 125.1 . . ?
C4A C3A C2A 108.5(3) . . ?
C4A C3A H3A 125.7 . . ?
C2A C3A H3A 125.7 . . ?
C5A C4A C3A 126.3(3) . . ?
C5A C4A C10A 127.3(2) . . ?
C3A C4A C10A 106.4(2) . . ?
C6A C5A C4A 128.8(3) . . ?
C6A C5A H5A 115.6 . . ?
C4A C5A H5A 115.6 . . ?
C5A C6A C7A 129.7(3) . . ?
C5A C6A H6A 115.2 . . ?
C7A C6A H6A 115.2 . . ?
C8A C7A C6A 129.1(3) . . ?
C8A C7A H7A 115.5 . . ?
C6A C7A H7A 115.5 . . ?
C7A C8A C9A 129.1(3) . . ?
C7A C8A H8A 115.4 . . ?
C9A C8A H8A 115.4 . . ?
C10A C9A C8A 128.5(3) . . ?
C10A C9A H9A 115.8 . . ?
C8A C9A H9A 115.8 . . ?
C9A C10A C1A 125.9(3) . . ?
C9A C10A C4A 127.5(2) . . ?
C1A C10A C4A 106.6(2) . . ?
C6S C1S C2S 117.4(3) . . ?
C6S C1S I1S 122.0(2) . . ?
C2S C1S I1S 120.6(2) . . ?
F1S C2S C1S 120.5(3) . . ?
F1S C2S C3S 118.8(3) . . ?
C1S C2S C3S 120.8(3) . . ?
F2S C3S C4S 120.9(3) . . ?
F2S C3S C2S 118.0(3) . . ?
C4S C3S C2S 121.1(3) . . ?
C3S C4S C5S 117.7(3) . . ?
C3S C4S I2S 120.7(2) . . ?
C5S C4S I2S 121.5(2) . . ?
F3S C5S C6S 119.1(3) . . ?
F3S C5S C4S 120.0(3) . . ?
C6S C5S C4S 120.9(3) . . ?
F4S C6S C1S 119.7(3) . . ?
F4S C6S C5S 118.2(3) . . ?
C1S C6S C5S 122.1(3) . . ?
C3T C1T C2T 117.1(3) 2_666 . ?
C3T C1T I1T 121.6(2) 2_666 . ?
C2T C1T I1T 121.3(2) . . ?
F2T C2T C3T 118.7(2) . . ?
F2T C2T C1T 120.0(3) . . ?
C3T C2T C1T 121.3(3) . . ?
F1T C3T C2T 118.3(3) . . ?
F1T C3T C1T 120.1(3) . 2_666 ?
C2T C3T C1T 121.6(3) . 2_666 ?

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
C10A C1A C2A C3A -0.8(3) . . . . ?
C1A C2A C3A C4A 0.6(4) . . . . ?
C2A C3A C4A C5A 179.9(3) . . . . ?
C2A C3A C4A C10A -0.2(3) . . . . ?
C3A C4A C5A C6A -179.0(3) . . . . ?
C10A C4A C5A C6A 1.2(5) . . . . ?
C4A C5A C6A C7A -3.0(6) . . . . ?
C5A C6A C7A C8A 2.7(6) . . . . ?
C6A C7A C8A C9A -0.8(6) . . . . ?
C7A C8A C9A C10A -0.4(6) . . . . ?
C8A C9A C10A C1A -179.3(3) . . . . ?
C8A C9A C10A C4A 0.0(5) . . . . ?
C2A C1A C10A C9A 180.0(3) . . . . ?
C2A C1A C10A C4A 0.6(3) . . . . ?
C5A C4A C10A C9A 0.3(5) . . . . ?
C3A C4A C10A C9A -179.6(3) . . . . ?
C5A C4A C10A C1A 179.6(3) . . . . ?
C3A C4A C10A C1A -0.2(3) . . . . ?
C6S C1S C2S F1S 179.2(3) . . . . ?
I1S C1S C2S F1S 0.1(4) . . . . ?
C6S C1S C2S C3S 0.0(5) . . . . ?
I1S C1S C2S C3S -179.2(2) . . . . ?
F1S C2S C3S F2S 0.7(4) . . . . ?
C1S C2S C3S F2S 179.9(3) . . . . ?
F1S C2S C3S C4S -178.8(3) . . . . ?
C1S C2S C3S C4S 0.4(5) . . . . ?
F2S C3S C4S C5S -180.0(3) . . . . ?
C2S C3S C4S C5S -0.5(5) . . . . ?
F2S C3S C4S I2S -0.6(4) . . . . ?
C2S C3S C4S I2S 178.8(2) . . . . ?
C3S C4S C5S F3S -178.7(3) . . . . ?
I2S C4S C5S F3S 2.0(4) . . . . ?
C3S C4S C5S C6S 0.2(5) . . . . ?
I2S C4S C5S C6S -179.2(2) . . . . ?
C2S C1S C6S F4S 179.5(3) . . . . ?
I1S C1S C6S F4S -1.4(4) . . . . ?
C2S C1S C6S C5S -0.3(5) . . . . ?
I1S C1S C6S C5S 178.8(2) . . . . ?
F3S C5S C6S F4S -0.7(4) . . . . ?
C4S C5S C6S F4S -179.6(3) . . . . ?
F3S C5S C6S C1S 179.1(3) . . . . ?
C4S C5S C6S C1S 0.2(5) . . . . ?
C3T C1T C2T F2T 179.3(3) 2_666 . . . ?
I1T C1T C2T F2T -1.3(4) . . . . ?
C3T C1T C2T C3T 1.0(5) 2_666 . . . ?
I1T C1T C2T C3T -179.5(2) . . . . ?
F2T C2T C3T F1T 1.5(4) . . . . ?
C1T C2T C3T F1T 179.8(3) . . . . ?
F2T C2T C3T C1T -179.3(3) . . . 2_666 ?
C1T C2T C3T C1T -1.1(5) . . . 2_666 ?

_refine_diff_density_max         0.894
_refine_diff_density_min         -1.083
_refine_diff_density_rms         0.108


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol/chlorofom'
####################################################################### 
# 
# 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_azu_ofiab_1-2_150K
_database_code_depnum_ccdc_archive 'CCDC 2000774'
loop_
_audit_author_name
_audit_author_address
'Filip Topic'
;McGill University
Canada
;
_audit_update_record             
;
2020-05-03 deposited with the CCDC.	2020-11-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_formula_moiety         '2(C12 F8 I2 N2), C10 H8'
_chemical_formula_sum            'C34 H8 F16 I4 N4'
_chemical_formula_weight         1284.04

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   6.0619(9)
_cell_length_b                   11.9613(17)
_cell_length_c                   12.6449(18)
_cell_angle_alpha                88.7995(16)
_cell_angle_beta                 79.8911(17)
_cell_angle_gamma                88.7903(17)
_cell_volume                     902.3(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    150.0(1)
_cell_measurement_reflns_used    4753
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      28.22

_exptl_crystal_description       rod
_exptl_crystal_colour            'dark brown'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.363
_exptl_crystal_F_000             596
_exptl_crystal_size_max          0.660
_exptl_crystal_size_mid          0.164
_exptl_crystal_size_min          0.104
_exptl_absorpt_coefficient_mu    3.571
_shelx_estimated_absorpt_T_min   0.202
_shelx_estimated_absorpt_T_max   0.708
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.1409
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;

_diffrn_ambient_temperature      150.0(1)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Incoatec Microfocus X-ray Source I\mS (Mo)'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-DUO, Dual, APEX-II'
_diffrn_detector                 CCD
_diffrn_detector_type            APEX-II
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            11017
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.636
_diffrn_reflns_theta_max         28.968
_diffrn_reflns_theta_full        25.250
_diffrn_measured_fraction_theta_max 0.909
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.909
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.909
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4351
_reflns_number_gt                3476
_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       'Bruker APEX3'
_computing_cell_refinement       'Bruker APEX3'
_computing_data_reduction        'Bruker APEX3'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_publication_material  
'OLEX2 (Dolomanov et al., 2009) & WinGX (Farrugia, 2012)'

_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)+(0.0351P)²+0.1255P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick, 2015)'
_refine_ls_extinction_coef       0.0016(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4351
_refine_ls_number_parameters     375
_refine_ls_number_restraints     1411
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0285
_refine_ls_wR_factor_ref         0.0722
_refine_ls_wR_factor_gt          0.0666
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      0.937
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

# start Validation Reply Form
_vrf_PLAT250_azu_ofiab_1-2_150K  
;
PROBLEM: Large U3/U1 Ratio for Average U(i,j) Tensor ....        4.3 Note  
RESPONSE: This is due to disorder of both coformers.
;
# end Validation Reply Form

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 1.207(2) 0.4637(11) 0.1177(10) 0.053(3) Uani 0.5 1 d D U P A -1
H1A H 1.331871 0.491164 0.144880 0.064 Uiso 0.5 1 calc R U P A -1
C2A C 1.088(2) 0.3672(11) 0.1528(12) 0.0599(12) Uani 0.5 1 d D U P A -1
H2A H 1.120939 0.318840 0.208778 0.072 Uiso 0.5 1 calc R U P A -1
C3A C 0.916(2) 0.3509(10) 0.0951(11) 0.056(3) Uani 0.5 1 d D U P A -1
H3A H 0.813128 0.291178 0.105323 0.067 Uiso 0.5 1 calc R U P A -1
C4A C 0.9214(10) 0.4383(5) 0.0196(5) 0.0345(15) Uani 0.5 1 d D U P A -1
C5A C 0.7775(11) 0.4536(6) -0.0532(5) 0.0457(17) Uani 0.5 1 d D U P A -1
H5A H 0.665209 0.398853 -0.050071 0.055 Uiso 0.5 1 calc R U P A -1
C6A C 0.774(2) 0.5375(11) -0.1299(11) 0.054(3) Uani 0.5 1 d D U P A -1
H6A H 0.663099 0.530340 -0.173746 0.065 Uiso 0.5 1 calc R U P A -1
C7A C 0.908(2) 0.6299(11) -0.1524(12) 0.0599(12) Uani 0.5 1 d D U P A -1
H7A H 0.873211 0.678973 -0.207590 0.072 Uiso 0.5 1 calc R U P A -1
C8A C 1.085(2) 0.6597(11) -0.1046(10) 0.051(3) Uani 0.5 1 d D U P A -1
H8A H 1.156412 0.726550 -0.132633 0.062 Uiso 0.5 1 calc R U P A -1
C9A C 1.1749(12) 0.6083(5) -0.0225(6) 0.0425(17) Uani 0.5 1 d D U P A -1
H9A H 1.299762 0.644567 -0.003267 0.051 Uiso 0.5 1 calc R U P A -1
C10A C 1.1098(11) 0.5124(5) 0.0351(5) 0.0332(14) Uani 0.5 1 d D U P A -1
C1S C 0.5670(5) 0.6438(3) 0.4332(3) 0.0251(5) Uani 0.926(3) 1 d D U P B 1
C2S C 0.3744(5) 0.6899(3) 0.4043(3) 0.0271(7) Uani 0.926(3) 1 d D U P B 1
C3S C 0.2279(5) 0.7571(3) 0.4734(3) 0.0259(7) Uani 0.926(3) 1 d D U P B 1
C4S C 0.2684(5) 0.7798(3) 0.5764(3) 0.0251(5) Uani 0.926(3) 1 d D U P B 1
C5S C 0.4632(5) 0.7320(3) 0.6043(3) 0.0265(7) Uani 0.926(3) 1 d D U P B 1
C6S C 0.6067(6) 0.6654(3) 0.5347(3) 0.0266(7) Uani 0.926(3) 1 d D U P B 1
C7S C -0.4701(5) 1.1006(3) 0.8372(3) 0.0221(7) Uani 0.926(3) 1 d D U P B 1
C8S C -0.5043(5) 1.0726(3) 0.7359(2) 0.0225(6) Uani 0.926(3) 1 d D U P B 1
C9S C -0.3547(5) 1.0037(3) 0.6722(2) 0.0235(7) Uani 0.926(3) 1 d D U P B 1
C10S C -0.1626(5) 0.9595(3) 0.7057(2) 0.0222(7) Uani 0.926(3) 1 d D U P B 1
C11S C -0.1290(5) 0.9883(3) 0.8079(2) 0.0215(6) Uani 0.926(3) 1 d D U P B 1
C12S C -0.2803(5) 1.0578(3) 0.8715(3) 0.0236(6) Uani 0.926(3) 1 d D U P B 1
F1S F 0.3281(4) 0.6730(2) 0.30597(19) 0.0359(6) Uani 0.926(3) 1 d D U P B 1
F2S F 0.0481(3) 0.79921(19) 0.43730(17) 0.0331(5) Uani 0.926(3) 1 d D U P B 1
F3S F 0.5108(4) 0.75011(19) 0.70187(17) 0.0357(6) Uani 0.926(3) 1 d D U P B 1
F4S F 0.7895(4) 0.6214(2) 0.5688(2) 0.0363(6) Uani 0.926(3) 1 d D U P B 1
F5S F -0.6853(4) 1.1121(2) 0.69803(19) 0.0326(6) Uani 0.926(3) 1 d D U P B 1
F6S F -0.3936(4) 0.97967(19) 0.57465(16) 0.0334(5) Uani 0.926(3) 1 d D U P B 1
F7S F 0.0502(3) 0.94957(19) 0.84696(17) 0.0295(5) Uani 0.926(3) 1 d D U P B 1
F8S F -0.2406(4) 1.0828(2) 0.96944(19) 0.0341(6) Uani 0.926(3) 1 d D U P B 1
N1S N 0.1409(5) 0.8489(3) 0.6553(2) 0.0303(7) Uani 0.926(3) 1 d D U P B 1
N2S N -0.0295(5) 0.8901(3) 0.6295(2) 0.0318(7) Uani 0.926(3) 1 d D U P B 1
I1S I 0.78995(4) 0.54958(2) 0.32493(2) 0.03444(9) Uani 1 1 d D . . . .
I2S I -0.69438(4) 1.20477(2) 0.93472(2) 0.03339(9) Uani 1 1 d D . . . .
C1T C 0.5408(15) 0.6468(10) 0.4157(7) 0.026(3) Uani 0.074(3) 1 d DG U P B 2
C2T C 0.5556(14) 0.6806(10) 0.5178(7) 0.026(3) Uani 0.074(3) 1 d DG U P B 2
C3T C 0.3935(13) 0.7496(9) 0.5757(6) 0.0265(7) Uani 0.074(3) 1 d G U P B 2
C4T C 0.2068(11) 0.7857(7) 0.5334(6) 0.026(3) Uani 0.074(3) 1 d G U P B 2
C5T C 0.1953(14) 0.7518(9) 0.4295(6) 0.0259(7) Uani 0.074(3) 1 d G U P B 2
C6T C 0.3562(15) 0.6828(10) 0.3729(7) 0.024(4) Uani 0.074(3) 1 d DG U P B 2
C7T C -0.4550(19) 1.0986(12) 0.8489(8) 0.024(4) Uani 0.074(3) 1 d DG U P B 2
C8T C -0.2708(19) 1.0610(13) 0.8911(8) 0.0236(6) Uani 0.074(3) 1 d DG U P B 2
C9T C -0.1090(17) 0.9937(11) 0.8328(7) 0.0215(6) Uani 0.074(3) 1 d G U P B 2
C10T C -0.1227(13) 0.9590(9) 0.7292(6) 0.0222(7) Uani 0.074(3) 1 d G U P B 2
C11T C -0.3101(15) 0.9960(10) 0.6879(7) 0.0235(7) Uani 0.074(3) 1 d G U P B 2
C12T C -0.4696(17) 1.0658(12) 0.7462(8) 0.0225(6) Uani 0.074(3) 1 d DG U P B 2
F1T F 0.7280(19) 0.6457(14) 0.5649(9) 0.028(4) Uani 0.074(3) 1 d G U P B 2
F2T F 0.4183(16) 0.7764(11) 0.6754(7) 0.029(4) Uani 0.074(3) 1 d G U P B 2
F3T F 0.0244(18) 0.7854(13) 0.3819(8) 0.026(4) Uani 0.074(3) 1 d G U P B 2
F4T F 0.335(2) 0.6529(14) 0.2733(8) 0.031(5) Uani 0.074(3) 1 d G U P B 2
F5T F -0.246(2) 1.0907(16) 0.9902(9) 0.031(5) Uani 0.074(3) 1 d G U P B 2
F6T F 0.065(2) 0.9579(14) 0.8776(8) 0.0295(5) Uani 0.074(3) 1 d G U P B 2
F7T F -0.3391(17) 0.9685(12) 0.5892(8) 0.0334(5) Uani 0.074(3) 1 d G U P B 2
F8T F -0.645(2) 1.0999(15) 0.7013(10) 0.028(5) Uani 0.074(3) 1 d G U P B 2
N1T N 0.0333(11) 0.8555(7) 0.5869(6) 0.026(4) Uani 0.074(3) 1 d G U P B 2
N2T N 0.0482(12) 0.8878(8) 0.6756(6) 0.028(4) Uani 0.074(3) 1 d G U P B 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 1.396(7) . ?
C1A C10A 1.399(7) . ?
C1A H1A 0.9500 . ?
C2A C3A 1.395(7) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.397(7) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.382(6) . ?
C4A C10A 1.502(7) . ?
C5A C6A 1.384(7) . ?
C5A H5A 0.9500 . ?
C6A C7A 1.379(7) . ?
C6A H6A 0.9500 . ?
C7A C8A 1.377(7) . ?
C7A H7A 0.9500 . ?
C8A C9A 1.384(7) . ?
C8A H8A 0.9500 . ?
C9A C10A 1.374(6) . ?
C9A H9A 0.9500 . ?
C1S C6S 1.377(4) . ?
C1S C2S 1.383(4) . ?
C1S I1S 2.079(3) . ?
C2S F1S 1.343(4) . ?
C2S C3S 1.387(4) . ?
C3S F2S 1.339(4) . ?
C3S C4S 1.400(4) . ?
C4S C5S 1.399(4) . ?
C4S N1S 1.419(4) . ?
C5S F3S 1.339(4) . ?
C5S C6S 1.377(4) . ?
C6S F4S 1.351(4) . ?
C7S C8S 1.381(4) . ?
C7S C12S 1.384(4) . ?
C7S I2S 2.080(3) . ?
C8S F5S 1.345(3) . ?
C8S C9S 1.375(4) . ?
C9S F6S 1.335(3) . ?
C9S C10S 1.397(4) . ?
C10S C11S 1.395(4) . ?
C10S N2S 1.414(4) . ?
C11S F7S 1.340(3) . ?
C11S C12S 1.385(4) . ?
C12S F8S 1.343(3) . ?
N1S N2S 1.228(4) . ?
I1S C1T 2.079(3) . ?
I2S C7T 2.079(3) . ?
C1T C2T 1.3789 . ?
C1T C6T 1.3831 . ?
C2T F1T 1.3457 . ?
C2T C3T 1.3866 . ?
C3T F2T 1.3408 . ?
C3T C4T 1.3918 . ?
C4T C5T 1.3963 . ?
C4T N1T 1.4139 . ?
C5T F3T 1.3373 . ?
C5T C6T 1.3744 . ?
C6T F4T 1.3447 . ?
C7T C12T 1.3820 . ?
C7T C8T 1.3830 . ?
C8T F5T 1.3442 . ?
C8T C9T 1.3755 . ?
C9T F6T 1.3385 . ?
C9T C10T 1.3989 . ?
C10T C11T 1.3911 . ?
C10T N2T 1.4139 . ?
C11T F7T 1.3397 . ?
C11T C12T 1.3848 . ?
C12T F8T 1.3448 . ?
N1T N2T 1.2128 . ?

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 C10A 107.5(9) . . ?
C2A C1A H1A 126.3 . . ?
C10A C1A H1A 126.3 . . ?
C3A C2A C1A 111.4(11) . . ?
C3A C2A H2A 124.3 . . ?
C1A C2A H2A 124.3 . . ?
C2A C3A C4A 107.7(9) . . ?
C2A C3A H3A 126.1 . . ?
C4A C3A H3A 126.1 . . ?
C5A C4A C3A 126.1(7) . . ?
C5A C4A C10A 127.3(5) . . ?
C3A C4A C10A 106.6(5) . . ?
C4A C5A C6A 129.1(7) . . ?
C4A C5A H5A 115.5 . . ?
C6A C5A H5A 115.5 . . ?
C7A C6A C5A 129.8(11) . . ?
C7A C6A H6A 115.1 . . ?
C5A C6A H6A 115.1 . . ?
C8A C7A C6A 127.9(12) . . ?
C8A C7A H7A 116.1 . . ?
C6A C7A H7A 116.1 . . ?
C7A C8A C9A 130.6(11) . . ?
C7A C8A H8A 114.7 . . ?
C9A C8A H8A 114.7 . . ?
C10A C9A C8A 129.2(7) . . ?
C10A C9A H9A 115.4 . . ?
C8A C9A H9A 115.4 . . ?
C9A C10A C1A 127.0(7) . . ?
C9A C10A C4A 126.2(5) . . ?
C1A C10A C4A 106.8(5) . . ?
C6S C1S C2S 117.4(3) . . ?
C6S C1S I1S 121.9(2) . . ?
C2S C1S I1S 120.7(2) . . ?
F1S C2S C1S 120.1(3) . . ?
F1S C2S C3S 118.0(3) . . ?
C1S C2S C3S 121.9(3) . . ?
F2S C3S C2S 117.3(3) . . ?
F2S C3S C4S 121.8(3) . . ?
C2S C3S C4S 121.0(3) . . ?
C5S C4S C3S 116.3(3) . . ?
C5S C4S N1S 115.4(3) . . ?
C3S C4S N1S 128.3(3) . . ?
F3S C5S C6S 118.9(3) . . ?
F3S C5S C4S 119.2(3) . . ?
C6S C5S C4S 121.9(3) . . ?
F4S C6S C1S 120.5(3) . . ?
F4S C6S C5S 118.0(3) . . ?
C1S C6S C5S 121.6(3) . . ?
C8S C7S C12S 117.8(3) . . ?
C8S C7S I2S 121.3(2) . . ?
C12S C7S I2S 120.9(2) . . ?
F5S C8S C9S 118.8(3) . . ?
F5S C8S C7S 120.5(3) . . ?
C9S C8S C7S 120.7(3) . . ?
F6S C9S C8S 118.6(3) . . ?
F6S C9S C10S 119.1(3) . . ?
C8S C9S C10S 122.3(3) . . ?
C11S C10S C9S 116.7(3) . . ?
C11S C10S N2S 129.1(3) . . ?
C9S C10S N2S 114.2(3) . . ?
F7S C11S C12S 118.4(3) . . ?
F7S C11S C10S 120.9(3) . . ?
C12S C11S C10S 120.7(3) . . ?
F8S C12S C7S 119.8(3) . . ?
F8S C12S C11S 118.4(3) . . ?
C7S C12S C11S 121.8(3) . . ?
N2S N1S C4S 114.4(3) . . ?
N1S N2S C10S 116.6(3) . . ?
C2T C1T C6T 117.8 . . ?
C2T C1T I1S 122.1(3) . . ?
C6T C1T I1S 120.1(3) . . ?
F1T C2T C1T 120.5 . . ?
F1T C2T C3T 117.9 . . ?
C1T C2T C3T 121.6 . . ?
F2T C3T C2T 117.7 . . ?
F2T C3T C4T 121.3 . . ?
C2T C3T C4T 120.9 . . ?
C3T C4T C5T 116.8 . . ?
C3T C4T N1T 124.7 . . ?
C5T C4T N1T 118.5 . . ?
F3T C5T C6T 117.7 . . ?
F3T C5T C4T 120.5 . . ?
C6T C5T C4T 121.8 . . ?
F4T C6T C5T 118.9 . . ?
F4T C6T C1T 120.0 . . ?
C5T C6T C1T 121.1 . . ?
C12T C7T C8T 117.4 . . ?
C12T C7T I2S 121.4(3) . . ?
C8T C7T I2S 121.1(3) . . ?
F5T C8T C9T 118.7 . . ?
F5T C8T C7T 120.3 . . ?
C9T C8T C7T 121.0 . . ?
F6T C9T C8T 118.9 . . ?
F6T C9T C10T 118.8 . . ?
C8T C9T C10T 122.2 . . ?
C11T C10T C9T 116.4 . . ?
C11T C10T N2T 124.9 . . ?
C9T C10T N2T 118.7 . . ?
F7T C11T C12T 117.6 . . ?
F7T C11T C10T 121.3 . . ?
C12T C11T C10T 121.0 . . ?
F8T C12T C7T 119.8 . . ?
F8T C12T C11T 118.2 . . ?
C7T C12T C11T 121.9 . . ?
N2T N1T C4T 118.1 . . ?
N1T N2T C10T 118.6 . . ?

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
C10A C1A C2A C3A 0.3(7) . . . . ?
C1A C2A C3A C4A 0.3(7) . . . . ?
C2A C3A C4A C5A -179.7(7) . . . . ?
C2A C3A C4A C10A -0.7(8) . . . . ?
C3A C4A C5A C6A -179.7(16) . . . . ?
C10A C4A C5A C6A 1.6(15) . . . . ?
C4A C5A C6A C7A -2.3(19) . . . . ?
C5A C6A C7A C8A 2.1(17) . . . . ?
C6A C7A C8A C9A -0.8(16) . . . . ?
C7A C8A C9A C10A -0.6(18) . . . . ?
C8A C9A C10A C1A 179.9(15) . . . . ?
C8A C9A C10A C4A 1.2(14) . . . . ?
C2A C1A C10A C9A -179.7(7) . . . . ?
C2A C1A C10A C4A -0.7(8) . . . . ?
C5A C4A C10A C9A -1.2(12) . . . . ?
C3A C4A C10A C9A 179.9(9) . . . . ?
C5A C4A C10A C1A 179.8(9) . . . . ?
C3A C4A C10A C1A 0.9(9) . . . . ?
C6S C1S C2S F1S 179.1(3) . . . . ?
I1S C1S C2S F1S 0.8(5) . . . . ?
C6S C1S C2S C3S 1.2(5) . . . . ?
I1S C1S C2S C3S -177.2(3) . . . . ?
F1S C2S C3S F2S 0.9(5) . . . . ?
C1S C2S C3S F2S 178.9(3) . . . . ?
F1S C2S C3S C4S -178.8(3) . . . . ?
C1S C2S C3S C4S -0.8(5) . . . . ?
F2S C3S C4S C5S -179.3(3) . . . . ?
C2S C3S C4S C5S 0.4(5) . . . . ?
F2S C3S C4S N1S -1.8(6) . . . . ?
C2S C3S C4S N1S 177.9(3) . . . . ?
C3S C4S C5S F3S -179.6(3) . . . . ?
N1S C4S C5S F3S 2.5(5) . . . . ?
C3S C4S C5S C6S -0.4(5) . . . . ?
N1S C4S C5S C6S -178.3(3) . . . . ?
C2S C1S C6S F4S 178.8(3) . . . . ?
I1S C1S C6S F4S -2.9(5) . . . . ?
C2S C1S C6S C5S -1.2(5) . . . . ?
I1S C1S C6S C5S 177.1(3) . . . . ?
F3S C5S C6S F4S 0.1(5) . . . . ?
C4S C5S C6S F4S -179.1(3) . . . . ?
F3S C5S C6S C1S -179.9(3) . . . . ?
C4S C5S C6S C1S 0.9(5) . . . . ?
C12S C7S C8S F5S -179.7(3) . . . . ?
I2S C7S C8S F5S -0.3(4) . . . . ?
C12S C7S C8S C9S 0.5(5) . . . . ?
I2S C7S C8S C9S 180.0(3) . . . . ?
F5S C8S C9S F6S 0.7(5) . . . . ?
C7S C8S C9S F6S -179.5(3) . . . . ?
F5S C8S C9S C10S 179.9(3) . . . . ?
C7S C8S C9S C10S -0.3(5) . . . . ?
F6S C9S C10S C11S 179.3(3) . . . . ?
C8S C9S C10S C11S 0.1(5) . . . . ?
F6S C9S C10S N2S -1.1(5) . . . . ?
C8S C9S C10S N2S 179.7(3) . . . . ?
C9S C10S C11S F7S 179.8(3) . . . . ?
N2S C10S C11S F7S 0.2(6) . . . . ?
C9S C10S C11S C12S -0.2(5) . . . . ?
N2S C10S C11S C12S -179.7(3) . . . . ?
C8S C7S C12S F8S -179.9(3) . . . . ?
I2S C7S C12S F8S 0.6(4) . . . . ?
C8S C7S C12S C11S -0.6(5) . . . . ?
I2S C7S C12S C11S 180.0(3) . . . . ?
F7S C11S C12S F8S -0.2(5) . . . . ?
C10S C11S C12S F8S 179.8(3) . . . . ?
F7S C11S C12S C7S -179.5(3) . . . . ?
C10S C11S C12S C7S 0.4(5) . . . . ?
C5S C4S N1S N2S -179.9(3) . . . . ?
C3S C4S N1S N2S 2.6(5) . . . . ?
C4S N1S N2S C10S 179.9(3) . . . . ?
C11S C10S N2S N1S -0.2(6) . . . . ?
C9S C10S N2S N1S -179.8(3) . . . . ?
C6T C1T C2T F1T 178.1 . . . . ?
I1S C1T C2T F1T -3.9(6) . . . . ?
C6T C1T C2T C3T -0.9 . . . . ?
I1S C1T C2T C3T 177.1(6) . . . . ?
F1T C2T C3T F2T -0.4 . . . . ?
C1T C2T C3T F2T 178.6 . . . . ?
F1T C2T C3T C4T -177.8 . . . . ?
C1T C2T C3T C4T 1.2 . . . . ?
F2T C3T C4T C5T -179.0 . . . . ?
C2T C3T C4T C5T -1.8 . . . . ?
F2T C3T C4T N1T 2.5 . . . . ?
C2T C3T C4T N1T 179.7 . . . . ?
C3T C4T C5T F3T -178.2 . . . . ?
N1T C4T C5T F3T 0.4 . . . . ?
C3T C4T C5T C6T 2.2 . . . . ?
N1T C4T C5T C6T -179.2 . . . . ?
F3T C5T C6T F4T 0.1 . . . . ?
C4T C5T C6T F4T 179.7 . . . . ?
F3T C5T C6T C1T 178.3 . . . . ?
C4T C5T C6T C1T -2.0 . . . . ?
C2T C1T C6T F4T 179.5 . . . . ?
I1S C1T C6T F4T 1.5(6) . . . . ?
C2T C1T C6T C5T 1.3 . . . . ?
I1S C1T C6T C5T -176.7(6) . . . . ?
C12T C7T C8T F5T 179.4 . . . . ?
I2S C7T C8T F5T 1.5(8) . . . . ?
C12T C7T C8T C9T 0.0 . . . . ?
I2S C7T C8T C9T -177.9(8) . . . . ?
F5T C8T C9T F6T 1.7 . . . . ?
C7T C8T C9T F6T -179.0 . . . . ?
F5T C8T C9T C10T 179.9 . . . . ?
C7T C8T C9T C10T -0.7 . . . . ?
F6T C9T C10T C11T 178.1 . . . . ?
C8T C9T C10T C11T -0.2 . . . . ?
F6T C9T C10T N2T -0.3 . . . . ?
C8T C9T C10T N2T -178.6 . . . . ?
C9T C10T C11T F7T 179.4 . . . . ?
N2T C10T C11T F7T -2.3 . . . . ?
C9T C10T C11T C12T 1.7 . . . . ?
N2T C10T C11T C12T -180.0 . . . . ?
C8T C7T C12T F8T 179.9 . . . . ?
I2S C7T C12T F8T -2.2(8) . . . . ?
C8T C7T C12T C11T 1.6 . . . . ?
I2S C7T C12T C11T 179.4(8) . . . . ?
F7T C11T C12T F8T 1.3 . . . . ?
C10T C11T C12T F8T 179.1 . . . . ?
F7T C11T C12T C7T 179.7 . . . . ?
C10T C11T C12T C7T -2.5 . . . . ?
C3T C4T N1T N2T 1.0 . . . . ?
C5T C4T N1T N2T -177.5 . . . . ?
C4T N1T N2T C10T 179.1 . . . . ?
C11T C10T N2T N1T -0.1 . . . . ?
C9T C10T N2T N1T 178.2 . . . . ?

_refine_diff_density_max         0.961
_refine_diff_density_min         -0.758
_refine_diff_density_rms         0.112

####################################################################### 
# 
# 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_azu_14tfib_2-3_253K
_database_code_depnum_ccdc_archive 'CCDC 2004308'
loop_
_audit_author_name
_audit_author_address
'Filip Topic'
;McGill University
Canada
;
_audit_update_record             
;
2020-05-17 deposited with the CCDC.	2020-11-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_formula_moiety         '3(C6 F4 I2), 2(C10 H8)'
_chemical_formula_sum            'C38 H16 F12 I6'
_chemical_formula_weight         1461.91

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   5.9617(2)
_cell_length_b                   12.0425(4)
_cell_length_c                   14.9758(5)
_cell_angle_alpha                73.9375(13)
_cell_angle_beta                 80.8173(15)
_cell_angle_gamma                85.0271(16)
_cell_volume                     1018.93(6)
_cell_formula_units_Z            1
_cell_measurement_temperature    253.0(1)
_cell_measurement_reflns_used    8317
_cell_measurement_theta_min      3.10
_cell_measurement_theta_max      72.52

_exptl_crystal_description       lath
_exptl_crystal_colour            'dark blue'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.382
_exptl_crystal_F_000             670
_exptl_crystal_size_max          0.942
_exptl_crystal_size_mid          0.329
_exptl_crystal_size_min          0.098
_exptl_absorpt_coefficient_mu    36.666
_shelx_estimated_absorpt_T_min   0.013
_shelx_estimated_absorpt_T_max   0.124
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.0032
_exptl_absorpt_correction_T_max  0.2335
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;

_diffrn_ambient_temperature      253.0(1)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Incoatec Microfocus X-ray Source I\mS (Cu)'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'Bruker D8 Venture, Dual, Cu at zero, PHOTON II'
_diffrn_detector                 CPAD
_diffrn_detector_type            'PHOTON II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            14753
_diffrn_reflns_av_unetI/netI     0.0545
_diffrn_reflns_av_R_equivalents  0.0632
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.102
_diffrn_reflns_theta_max         72.728
_diffrn_reflns_theta_full        67.750
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_point_group_measured_fraction_full 0.975
_reflns_number_total             3942
_reflns_number_gt                3210
_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       'Bruker APEX3'
_computing_cell_refinement       'Bruker APEX3'
_computing_data_reduction        'Bruker APEX3'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_publication_material  
'OLEX2 (Dolomanov et al., 2009) & WinGX (Farrugia, 2012)'

_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)+(0.1571P)²+2.7429P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick, 2015)'
_refine_ls_extinction_coef       0.0071(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3942
_refine_ls_number_parameters     254
_refine_ls_number_restraints     34
_refine_ls_R_factor_all          0.0818
_refine_ls_R_factor_gt           0.0719
_refine_ls_wR_factor_ref         0.2292
_refine_ls_wR_factor_gt          0.2037
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.035
_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 0.3335(15) 0.4958(7) 0.3180(5) 0.059(2) Uani 1 1 d D . . . .
H1A H 0.203803 0.483332 0.362550 0.071 Uiso 1 1 calc R U . . .
C2A C 0.5111(14) 0.5659(7) 0.3150(6) 0.067(3) Uani 1 1 d D . . . .
H2A H 0.515759 0.608467 0.357804 0.081 Uiso 1 1 calc R U . . .
C3A C 0.6809(16) 0.5638(7) 0.2392(6) 0.066(3) Uani 1 1 d D . . . .
H3A H 0.814009 0.604159 0.223403 0.080 Uiso 1 1 calc R U . . .
C4A C 0.6147(12) 0.4901(6) 0.1912(5) 0.060(2) Uani 1 1 d D . . . .
C5A C 0.7337(15) 0.4647(7) 0.1119(6) 0.066(2) Uani 1 1 d D . . . .
H5A H 0.870393 0.501220 0.088874 0.080 Uiso 1 1 calc R U . . .
C6A C 0.6794(14) 0.3939(7) 0.0624(6) 0.055(2) Uani 1 1 d D . . . .
H6A H 0.787507 0.387080 0.011847 0.066 Uiso 1 1 calc R U . . .
C7A C 0.4865(13) 0.3301(7) 0.0759(6) 0.057(2) Uani 1 1 d D . . . .
H7A H 0.481757 0.288083 0.032776 0.068 Uiso 1 1 calc R U . . .
C8A C 0.3005(16) 0.3218(7) 0.1462(6) 0.064(2) Uani 1 1 d D . . . .
H8A H 0.188363 0.274265 0.143356 0.077 Uiso 1 1 calc R U . . .
C9A C 0.2563(13) 0.3727(7) 0.2191(6) 0.058(2) Uani 1 1 d D . . . .
H9A H 0.120067 0.354217 0.258637 0.070 Uiso 1 1 calc R U . . .
C10A C 0.3869(12) 0.4474(6) 0.2414(5) 0.058(2) Uani 1 1 d D . . . .
C1S C 0.8699(15) 0.1949(7) 0.5474(5) 0.0481(18) Uani 1 1 d . . . . .
C2S C 0.8234(14) 0.0777(7) 0.5718(6) 0.0472(17) Uani 1 1 d . . . . .
C3S C 0.9348(14) -0.0038(7) 0.6314(6) 0.0461(17) Uani 1 1 d . . . . .
C4S C 1.1115(13) 0.0245(6) 0.6729(5) 0.0420(15) Uani 1 1 d . . . . .
C5S C 1.1553(15) 0.1391(7) 0.6499(6) 0.0477(17) Uani 1 1 d . . . . .
C6S C 1.0402(16) 0.2229(7) 0.5886(6) 0.0494(18) Uani 1 1 d . . . . .
F1S F 0.6576(11) 0.0447(6) 0.5342(5) 0.0736(16) Uani 1 1 d . . . . .
F2S F 0.8861(10) -0.1159(4) 0.6509(5) 0.0669(14) Uani 1 1 d . . . . .
F3S F 1.3216(12) 0.1726(5) 0.6874(5) 0.0727(16) Uani 1 1 d . . . . .
F4S F 1.0946(12) 0.3337(5) 0.5693(5) 0.0743(17) Uani 1 1 d . . . . .
I1S I 0.69716(13) 0.31806(6) 0.45441(4) 0.0697(3) Uani 1 1 d . . . . .
I2S I 1.28727(11) -0.10127(5) 0.76275(4) 0.0616(3) Uani 1 1 d . . . . .
C1T C 0.1158(14) 0.9135(6) 0.0627(5) 0.0398(15) Uani 1 1 d . . . . .
C2T C -0.0554(15) 0.8873(6) 0.0203(6) 0.0440(17) Uani 1 1 d . . . . .
C3T C -0.1641(15) 0.9716(7) -0.0407(6) 0.0446(17) Uani 1 1 d . . . . .
F1T F -0.3318(12) 0.9405(5) -0.0796(5) 0.0719(18) Uani 1 1 d . . . . .
F2T F -0.1113(11) 0.7766(4) 0.0384(5) 0.0647(15) Uani 1 1 d . . . . .
I1T I 0.28519(10) 0.78627(4) 0.15547(3) 0.0536(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
C1A C2A 1.398(7) . ?
C1A C10A 1.407(6) . ?
C1A H1A 0.9300 . ?
C2A C3A 1.400(7) . ?
C2A H2A 0.9300 . ?
C3A C4A 1.401(6) . ?
C3A H3A 0.9300 . ?
C4A C5A 1.379(6) . ?
C4A C10A 1.501(8) . ?
C5A C6A 1.362(7) . ?
C5A H5A 0.9300 . ?
C6A C7A 1.395(6) . ?
C6A H6A 0.9300 . ?
C7A C8A 1.391(6) . ?
C7A H7A 0.9300 . ?
C8A C9A 1.373(6) . ?
C8A H8A 0.9300 . ?
C9A C10A 1.378(6) . ?
C9A H9A 0.9300 . ?
C1S C6S 1.378(13) . ?
C1S C2S 1.397(12) . ?
C1S I1S 2.062(8) . ?
C2S C3S 1.339(13) . ?
C2S F1S 1.350(10) . ?
C3S F2S 1.346(9) . ?
C3S C4S 1.415(12) . ?
C4S C5S 1.366(11) . ?
C4S I2S 2.061(8) . ?
C5S F3S 1.354(10) . ?
C5S C6S 1.378(12) . ?
C6S F4S 1.342(9) . ?
C1T C3T 1.376(11) 2_575 ?
C1T C2T 1.385(12) . ?
C1T I1T 2.074(8) . ?
C2T F2T 1.345(9) . ?
C2T C3T 1.359(12) . ?
C3T F1T 1.360(10) . ?

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 C10A 107.4(6) . . ?
C2A C1A H1A 126.3 . . ?
C10A C1A H1A 126.3 . . ?
C1A C2A C3A 111.3(7) . . ?
C1A C2A H2A 124.4 . . ?
C3A C2A H2A 124.4 . . ?
C2A C3A C4A 107.8(6) . . ?
C2A C3A H3A 126.1 . . ?
C4A C3A H3A 126.1 . . ?
C5A C4A C3A 126.4(6) . . ?
C5A C4A C10A 127.0(5) . . ?
C3A C4A C10A 106.6(5) . . ?
C6A C5A C4A 129.2(7) . . ?
C6A C5A H5A 115.4 . . ?
C4A C5A H5A 115.4 . . ?
C5A C6A C7A 129.9(7) . . ?
C5A C6A H6A 115.1 . . ?
C7A C6A H6A 115.1 . . ?
C8A C7A C6A 127.9(7) . . ?
C8A C7A H7A 116.1 . . ?
C6A C7A H7A 116.1 . . ?
C9A C8A C7A 130.2(7) . . ?
C9A C8A H8A 114.9 . . ?
C7A C8A H8A 114.9 . . ?
C8A C9A C10A 128.6(7) . . ?
C8A C9A H9A 115.7 . . ?
C10A C9A H9A 115.7 . . ?
C9A C10A C1A 126.0(6) . . ?
C9A C10A C4A 127.1(5) . . ?
C1A C10A C4A 106.8(5) . . ?
C6S C1S C2S 115.9(7) . . ?
C6S C1S I1S 122.1(6) . . ?
C2S C1S I1S 122.1(7) . . ?
C3S C2S F1S 118.1(8) . . ?
C3S C2S C1S 123.1(8) . . ?
F1S C2S C1S 118.8(8) . . ?
C2S C3S F2S 120.6(8) . . ?
C2S C3S C4S 121.2(7) . . ?
F2S C3S C4S 118.2(8) . . ?
C5S C4S C3S 115.7(7) . . ?
C5S C4S I2S 123.0(6) . . ?
C3S C4S I2S 121.3(6) . . ?
F3S C5S C4S 118.9(8) . . ?
F3S C5S C6S 118.1(7) . . ?
C4S C5S C6S 122.9(8) . . ?
F4S C6S C5S 119.2(8) . . ?
F4S C6S C1S 119.6(8) . . ?
C5S C6S C1S 121.2(7) . . ?
C3T C1T C2T 116.3(7) 2_575 . ?
C3T C1T I1T 122.2(6) 2_575 . ?
C2T C1T I1T 121.5(6) . . ?
F2T C2T C3T 119.7(8) . . ?
F2T C2T C1T 119.5(8) . . ?
C3T C2T C1T 120.8(7) . . ?
C2T C3T F1T 118.1(7) . . ?
C2T C3T C1T 122.9(8) . 2_575 ?
F1T C3T C1T 119.0(8) . 2_575 ?

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
C10A C1A C2A C3A -0.8(11) . . . . ?
C1A C2A C3A C4A -0.3(11) . . . . ?
C2A C3A C4A C5A 179.5(9) . . . . ?
C2A C3A C4A C10A 1.2(10) . . . . ?
C3A C4A C5A C6A 179.7(10) . . . . ?
C10A C4A C5A C6A -2.3(16) . . . . ?
C4A C5A C6A C7A 2.2(18) . . . . ?
C5A C6A C7A C8A -1.3(17) . . . . ?
C6A C7A C8A C9A 0.2(17) . . . . ?
C7A C8A C9A C10A 0.6(17) . . . . ?
C8A C9A C10A C1A -179.1(9) . . . . ?
C8A C9A C10A C4A -1.2(15) . . . . ?
C2A C1A C10A C9A 179.7(9) . . . . ?
C2A C1A C10A C4A 1.4(10) . . . . ?
C5A C4A C10A C9A 1.8(14) . . . . ?
C3A C4A C10A C9A -179.9(8) . . . . ?
C5A C4A C10A C1A -179.9(9) . . . . ?
C3A C4A C10A C1A -1.6(9) . . . . ?
C6S C1S C2S C3S 0.1(12) . . . . ?
I1S C1S C2S C3S 179.4(6) . . . . ?
C6S C1S C2S F1S 179.7(8) . . . . ?
I1S C1S C2S F1S -1.0(10) . . . . ?
F1S C2S C3S F2S 1.8(12) . . . . ?
C1S C2S C3S F2S -178.6(7) . . . . ?
F1S C2S C3S C4S 179.6(7) . . . . ?
C1S C2S C3S C4S -0.8(13) . . . . ?
C2S C3S C4S C5S 1.4(12) . . . . ?
F2S C3S C4S C5S 179.3(7) . . . . ?
C2S C3S C4S I2S -178.9(6) . . . . ?
F2S C3S C4S I2S -1.0(10) . . . . ?
C3S C4S C5S F3S 179.7(8) . . . . ?
I2S C4S C5S F3S 0.0(11) . . . . ?
C3S C4S C5S C6S -1.4(12) . . . . ?
I2S C4S C5S C6S 178.9(6) . . . . ?
F3S C5S C6S F4S -0.7(12) . . . . ?
C4S C5S C6S F4S -179.6(8) . . . . ?
F3S C5S C6S C1S 179.6(8) . . . . ?
C4S C5S C6S C1S 0.7(14) . . . . ?
C2S C1S C6S F4S -179.6(7) . . . . ?
I1S C1S C6S F4S 1.0(11) . . . . ?
C2S C1S C6S C5S 0.0(12) . . . . ?
I1S C1S C6S C5S -179.3(6) . . . . ?
C3T C1T C2T F2T 179.8(7) 2_575 . . . ?
I1T C1T C2T F2T -1.0(11) . . . . ?
C3T C1T C2T C3T 1.2(13) 2_575 . . . ?
I1T C1T C2T C3T -179.7(6) . . . . ?
F2T C2T C3T F1T 1.8(13) . . . . ?
C1T C2T C3T F1T -179.6(8) . . . . ?
F2T C2T C3T C1T -179.9(8) . . . 2_575 ?
C1T C2T C3T C1T -1.2(14) . . . 2_575 ?

_refine_diff_density_max         1.582
_refine_diff_density_min         -2.329
_refine_diff_density_rms         0.259

####################################################################### 
# 
# 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_azu_ofiab_3-2_253K
_database_code_depnum_ccdc_archive 'CCDC 2000775'
loop_
_audit_author_name
_audit_author_address
'Filip Topic'
;McGill University
Canada
;
_audit_update_record             
;
2020-05-03 deposited with the CCDC.	2020-11-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_formula_moiety         '2(C12 F8 I2 N2), 3(C10 H8)'
_chemical_formula_sum            'C54 H24 F16 I4 N4'
_chemical_formula_weight         1540.37

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'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   6.0053(3)
_cell_length_b                   11.9473(5)
_cell_length_c                   18.8788(7)
_cell_angle_alpha                71.556(4)
_cell_angle_beta                 89.199(3)
_cell_angle_gamma                83.434(4)
_cell_volume                     1276.14(10)
_cell_formula_units_Z            1
_cell_measurement_temperature    253.0(1)
_cell_measurement_reflns_used    4721
_cell_measurement_theta_min      2.4560
_cell_measurement_theta_max      77.5740

_exptl_crystal_description       lath
_exptl_crystal_colour            'dark brown'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.004
_exptl_crystal_F_000             732
_exptl_crystal_size_max          0.173
_exptl_crystal_size_mid          0.076
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    20.086
_shelx_estimated_absorpt_T_min   0.129
_shelx_estimated_absorpt_T_max   0.584
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.37600
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      253.0(1)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Incoatec Microfocus X-ray Source I\mS (Cu)'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'Bruker D8 Venture, Dual, Cu at zero, PHOTON II'
_diffrn_detector                 CPAD
_diffrn_detector_type            'PHOTON II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            15831
_diffrn_reflns_av_unetI/netI     0.0450
_diffrn_reflns_av_R_equivalents  0.0515
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.468
_diffrn_reflns_theta_max         79.776
_diffrn_reflns_theta_full        67.750
_diffrn_measured_fraction_theta_max 0.923
_diffrn_measured_fraction_theta_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.923
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.923
_diffrn_reflns_point_group_measured_fraction_full 0.970
_reflns_number_total             5150
_reflns_number_gt                3616
_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       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_publication_material  
'OLEX2 (Dolomanov et al., 2009) & WinGX (Farrugia, 2012)'

_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)+(0.0604P)²+1.6616P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5150
_refine_ls_number_parameters     507
_refine_ls_number_restraints     2126
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0457
_refine_ls_wR_factor_ref         0.1346
_refine_ls_wR_factor_gt          0.1107
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      0.901
_refine_ls_shift/su_max          0.001
_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 0.7459(18) 0.2053(11) 0.5517(5) 0.068(3) Uani 0.658(8) 1 d D U P A 1
H1A H 0.867901 0.238575 0.525998 0.082 Uiso 0.658(8) 1 calc R U P A 1
C2A C 0.6009(19) 0.1403(11) 0.5276(5) 0.076(3) Uani 0.658(8) 1 d D U P A 1
H2A H 0.615830 0.121238 0.483572 0.091 Uiso 0.658(8) 1 calc R U P A 1
C3A C 0.4310(19) 0.1078(10) 0.5787(5) 0.068(3) Uani 0.658(8) 1 d D U P A 1
H3A H 0.313337 0.066429 0.573638 0.082 Uiso 0.658(8) 1 calc R U P A 1
C4A C 0.4685(12) 0.1484(7) 0.6386(4) 0.0529(19) Uani 0.658(8) 1 d D U P A 1
C5A C 0.3321(13) 0.1362(8) 0.6994(4) 0.060(2) Uani 0.658(8) 1 d D U P A 1
H5A H 0.211189 0.093430 0.700843 0.072 Uiso 0.658(8) 1 calc R U P A 1
C6A C 0.353(2) 0.1795(12) 0.7584(6) 0.062(3) Uani 0.658(8) 1 d D U P A 1
H6A H 0.244163 0.160602 0.794553 0.075 Uiso 0.658(8) 1 calc R U P A 1
C7A C 0.5097(19) 0.2468(12) 0.7717(7) 0.068(3) Uani 0.658(8) 1 d D U P A 1
H7A H 0.490828 0.268015 0.814984 0.081 Uiso 0.658(8) 1 calc R U P A 1
C8A C 0.691(2) 0.2869(12) 0.7293(6) 0.066(3) Uani 0.658(8) 1 d D U P A 1
H8A H 0.779035 0.329981 0.748859 0.079 Uiso 0.658(8) 1 calc R U P A 1
C9A C 0.7630(14) 0.2728(7) 0.6626(4) 0.059(2) Uani 0.658(8) 1 d D U P A 1
H9A H 0.888296 0.309842 0.642773 0.071 Uiso 0.658(8) 1 calc R U P A 1
C10A C 0.6741(11) 0.2114(7) 0.6214(4) 0.0523(19) Uani 0.658(8) 1 d D U P A 1
C1C C 0.664(3) 0.2940(19) 0.7227(10) 0.062(4) Uani 0.342(8) 1 d D U P A 2
H1C H 0.772491 0.341813 0.725960 0.075 Uiso 0.342(8) 1 calc R U P A 2
C2C C 0.482(4) 0.269(2) 0.7698(11) 0.065(4) Uani 0.342(8) 1 d D U P A 2
H2C H 0.454545 0.295088 0.810735 0.078 Uiso 0.342(8) 1 calc R U P A 2
C3C C 0.347(3) 0.1979(19) 0.7468(9) 0.060(4) Uani 0.342(8) 1 d D U P A 2
H3C H 0.215881 0.171152 0.769102 0.071 Uiso 0.342(8) 1 calc R U P A 2
C4C C 0.445(2) 0.1747(13) 0.6846(7) 0.054(3) Uani 0.342(8) 1 d D U P A 2
C5C C 0.357(2) 0.1137(14) 0.6427(8) 0.058(3) Uani 0.342(8) 1 d D U P A 2
H5C H 0.217705 0.088143 0.656912 0.069 Uiso 0.342(8) 1 calc R U P A 2
C6C C 0.450(4) 0.086(2) 0.5824(11) 0.067(4) Uani 0.342(8) 1 d D U P A 2
H6C H 0.375349 0.033223 0.566776 0.081 Uiso 0.342(8) 1 calc R U P A 2
C7C C 0.636(4) 0.123(2) 0.5411(11) 0.069(4) Uani 0.342(8) 1 d D U P A 2
H7C H 0.660017 0.098382 0.499107 0.083 Uiso 0.342(8) 1 calc R U P A 2
C8C C 0.790(3) 0.192(2) 0.5551(10) 0.065(4) Uani 0.342(8) 1 d D U P A 2
H8C H 0.907575 0.204489 0.522162 0.078 Uiso 0.342(8) 1 calc R U P A 2
C9C C 0.794(2) 0.2438(14) 0.6106(7) 0.061(3) Uani 0.342(8) 1 d D U P A 2
H9C H 0.908351 0.291669 0.607416 0.073 Uiso 0.342(8) 1 calc R U P A 2
C10C C 0.6540(19) 0.2349(12) 0.6699(7) 0.054(3) Uani 0.342(8) 1 d D U P A 2
C1B C 0.182(2) 0.4206(15) 0.4237(7) 0.066(5) Uani 0.5 1 d D U P B -1
H1B H 0.319947 0.379878 0.419337 0.079 Uiso 0.5 1 calc R U P B -1
C2B C 0.002(2) 0.4498(15) 0.3725(7) 0.072(5) Uani 0.5 1 d D U P B -1
H2B H 0.003071 0.431027 0.328250 0.087 Uiso 0.5 1 calc R U P B -1
C3B C -0.180(2) 0.5111(15) 0.3967(6) 0.063(5) Uani 0.5 1 d D U P B -1
H3B H -0.316747 0.540221 0.371492 0.076 Uiso 0.5 1 calc R U P B -1
C4B C -0.1191(12) 0.5211(9) 0.4654(5) 0.047(2) Uani 0.5 1 d D U P B -1
C5B C -0.2500(14) 0.5765(9) 0.5076(5) 0.054(2) Uani 0.5 1 d D U P B -1
H5B H -0.393444 0.608163 0.488274 0.065 Uiso 0.5 1 calc R U P B -1
C6B C -0.198(2) 0.5917(17) 0.5745(8) 0.068(5) Uani 0.5 1 d D U P B -1
H6B H -0.310582 0.633888 0.593228 0.082 Uiso 0.5 1 calc R U P B -1
C7B C -0.004(2) 0.5538(16) 0.6183(8) 0.070(5) Uani 0.5 1 d D U P B -1
H7B H -0.006209 0.571583 0.662832 0.084 Uiso 0.5 1 calc R U P B -1
C8B C 0.193(2) 0.4929(17) 0.6042(8) 0.069(5) Uani 0.5 1 d D U P B -1
H8B H 0.305795 0.476289 0.640554 0.083 Uiso 0.5 1 calc R U P B -1
C9B C 0.2467(15) 0.4531(10) 0.5443(5) 0.058(3) Uani 0.5 1 d D U P B -1
H9B H 0.390580 0.414113 0.545892 0.070 Uiso 0.5 1 calc R U P B -1
C10B C 0.1170(12) 0.4631(9) 0.4826(5) 0.050(2) Uani 0.5 1 d D U P B -1
C1S C 0.9265(8) 0.2524(5) 0.2598(3) 0.0467(11) Uani 0.944(5) 1 d D U P C 1
C2S C 0.7165(8) 0.2939(5) 0.2775(3) 0.0457(11) Uani 0.944(5) 1 d D U P C 1
C3S C 0.5868(8) 0.3865(5) 0.2275(3) 0.0474(12) Uani 0.944(5) 1 d D U P C 1
C4S C 0.6643(8) 0.4428(5) 0.1569(3) 0.0445(12) Uani 0.944(5) 1 d D U P C 1
C5S C 0.8771(8) 0.3993(5) 0.1399(3) 0.0471(12) Uani 0.944(5) 1 d D U P C 1
C6S C 1.0039(8) 0.3070(5) 0.1901(3) 0.0476(12) Uani 0.944(5) 1 d D U P C 1
C7S C -0.0083(8) 0.8634(5) -0.0479(3) 0.0498(12) Uani 0.944(5) 1 d D U P C 1
C8S C 0.2000(8) 0.8220(5) -0.0662(3) 0.0534(13) Uani 0.944(5) 1 d D U P C 1
C9S C 0.3301(8) 0.7275(5) -0.0168(3) 0.0508(12) Uani 0.944(5) 1 d D U P C 1
C10S C 0.2552(8) 0.6707(5) 0.0539(3) 0.0474(12) Uani 0.944(5) 1 d D U P C 1
C11S C 0.0426(8) 0.7139(5) 0.0715(3) 0.0492(12) Uani 0.944(5) 1 d D U P C 1
C12S C -0.0838(8) 0.8074(5) 0.0219(3) 0.0490(12) Uani 0.944(5) 1 d D U P C 1
F1S F 0.6352(6) 0.2444(4) 0.34545(19) 0.0660(10) Uani 0.944(5) 1 d D U P C 1
F2S F 0.3866(6) 0.4215(4) 0.2500(2) 0.0649(10) Uani 0.944(5) 1 d D U P C 1
F3S F 0.9605(6) 0.4491(3) 0.07260(19) 0.0618(10) Uani 0.944(5) 1 d D U P C 1
F4S F 1.2083(6) 0.2697(4) 0.1705(2) 0.0660(10) Uani 0.944(5) 1 d D U P C 1
F5S F 0.2802(7) 0.8721(4) -0.1345(2) 0.0732(11) Uani 0.944(5) 1 d D U P C 1
F6S F 0.5293(6) 0.6921(4) -0.0401(2) 0.0689(11) Uani 0.944(5) 1 d D U P C 1
F7S F -0.0383(6) 0.6627(4) 0.13857(19) 0.0633(10) Uani 0.944(5) 1 d D U P C 1
F8S F -0.2853(6) 0.8450(4) 0.0437(2) 0.0670(10) Uani 0.944(5) 1 d D U P C 1
N1S N 0.5543(9) 0.5391(5) 0.0993(3) 0.0575(13) Uani 0.944(5) 1 d D U P C 1
N2S N 0.3633(8) 0.5721(5) 0.1112(3) 0.0545(13) Uani 0.944(5) 1 d D U P C 1
I1S I 1.12042(7) 0.11194(4) 0.33626(3) 0.06934(17) Uani 1 1 d D . . . .
I2S I -0.20283(8) 1.00658(4) -0.12282(3) 0.07044(17) Uani 1 1 d D . . . .
C1T C 0.896(2) 0.2490(14) 0.2690(6) 0.0467(11) Uani 0.056(5) 1 d DG U P C 2
C2T C 0.943(2) 0.3113(16) 0.1969(7) 0.0476(12) Uani 0.056(5) 1 d DG U P C 2
C3T C 0.796(2) 0.4033(14) 0.1530(6) 0.0471(12) Uani 0.056(5) 1 d G U P C 2
C4T C 0.5910(17) 0.4367(11) 0.1798(5) 0.0445(12) Uani 0.056(5) 1 d G U P C 2
C5T C 0.545(2) 0.3732(18) 0.2532(7) 0.0474(12) Uani 0.056(5) 1 d G U P C 2
C6T C 0.694(3) 0.2826(18) 0.2962(7) 0.0457(11) Uani 0.056(5) 1 d DG U P C 2
C7T C 0.019(2) 0.8662(14) -0.0569(6) 0.0498(12) Uani 0.056(5) 1 d DG U P C 2
C8T C -0.030(2) 0.8049(16) 0.0152(7) 0.0490(12) Uani 0.056(5) 1 d DG U P C 2
C9T C 0.115(2) 0.7123(15) 0.0590(6) 0.0492(12) Uani 0.056(5) 1 d G U P C 2
C10T C 0.3198(18) 0.6783(12) 0.0320(5) 0.0474(12) Uani 0.056(5) 1 d G U P C 2
C11T C 0.368(3) 0.7423(18) -0.0410(7) 0.0508(12) Uani 0.056(5) 1 d G U P C 2
C12T C 0.220(3) 0.8334(18) -0.0841(7) 0.0534(13) Uani 0.056(5) 1 d DG U P C 2
F1T F 1.137(3) 0.282(2) 0.1668(9) 0.0660(10) Uani 0.056(5) 1 d G U P C 2
F2T F 0.853(3) 0.459(2) 0.0830(8) 0.0618(10) Uani 0.056(5) 1 d G U P C 2
F3T F 0.352(4) 0.401(3) 0.2829(10) 0.0649(10) Uani 0.056(5) 1 d G U P C 2
F4T F 0.639(4) 0.225(3) 0.3666(10) 0.0660(10) Uani 0.056(5) 1 d G U P C 2
F5T F -0.226(3) 0.834(3) 0.0441(10) 0.0670(10) Uani 0.056(5) 1 d G U P C 2
F6T F 0.055(3) 0.658(2) 0.1287(8) 0.0633(10) Uani 0.056(5) 1 d G U P C 2
F7T F 0.561(4) 0.715(3) -0.0712(10) 0.0689(11) Uani 0.056(5) 1 d G U P C 2
F8T F 0.276(4) 0.892(3) -0.1544(9) 0.0732(11) Uani 0.056(5) 1 d G U P C 2
N1T N 0.4342(17) 0.5310(12) 0.1375(5) 0.051(6) Uani 0.056(5) 1 d G U P C 2
N2T N 0.4767(18) 0.5848(12) 0.0749(5) 0.050(6) Uani 0.056(5) 1 d G U P C 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 1.399(6) . ?
C1A C10A 1.399(6) . ?
C1A H1A 0.9300 . ?
C2A C3A 1.396(6) . ?
C2A H2A 0.9300 . ?
C3A C4A 1.394(6) . ?
C3A H3A 0.9300 . ?
C4A C5A 1.380(5) . ?
C4A C10A 1.498(6) . ?
C5A C6A 1.380(6) . ?
C5A H5A 0.9300 . ?
C6A C7A 1.382(6) . ?
C6A H6A 0.9300 . ?
C7A C8A 1.383(6) . ?
C7A H7A 0.9300 . ?
C8A C9A 1.380(6) . ?
C8A H8A 0.9300 . ?
C9A C10A 1.375(5) . ?
C9A H9A 0.9300 . ?
C1C C2C 1.397(6) . ?
C1C C10C 1.397(6) . ?
C1C H1C 0.9300 . ?
C2C C3C 1.397(6) . ?
C2C H2C 0.9300 . ?
C3C C4C 1.396(6) . ?
C3C H3C 0.9300 . ?
C4C C5C 1.378(6) . ?
C4C C10C 1.498(6) . ?
C5C C6C 1.379(6) . ?
C5C H5C 0.9300 . ?
C6C C7C 1.385(6) . ?
C6C H6C 0.9300 . ?
C7C C8C 1.386(6) . ?
C7C H7C 0.9300 . ?
C8C C9C 1.381(6) . ?
C8C H8C 0.9300 . ?
C9C C10C 1.377(6) . ?
C9C H9C 0.9300 . ?
C1B C10B 1.394(6) . ?
C1B C2B 1.397(6) . ?
C1B H1B 0.9300 . ?
C2B C3B 1.397(6) . ?
C2B H2B 0.9300 . ?
C3B C4B 1.396(6) . ?
C3B H3B 0.9300 . ?
C4B C5B 1.374(5) . ?
C4B C10B 1.497(6) . ?
C5B C6B 1.377(6) . ?
C5B H5B 0.9300 . ?
C6B C7B 1.383(6) . ?
C6B H6B 0.9300 . ?
C7B C8B 1.384(6) . ?
C7B H7B 0.9300 . ?
C8B C9B 1.379(6) . ?
C8B H8B 0.9300 . ?
C9B C10B 1.377(6) . ?
C9B H9B 0.9300 . ?
C1S C6S 1.372(5) . ?
C1S C2S 1.378(5) . ?
C1S I1S 2.079(5) . ?
C2S F1S 1.342(5) . ?
C2S C3S 1.373(6) . ?
C3S F2S 1.335(5) . ?
C3S C4S 1.390(6) . ?
C4S C5S 1.396(6) . ?
C4S N1S 1.412(7) . ?
C5S F3S 1.338(5) . ?
C5S C6S 1.364(6) . ?
C6S F4S 1.345(5) . ?
C7S C8S 1.372(5) . ?
C7S C12S 1.373(6) . ?
C7S I2S 2.085(5) . ?
C8S F5S 1.346(5) . ?
C8S C9S 1.381(6) . ?
C9S F6S 1.338(5) . ?
C9S C10S 1.387(6) . ?
C10S C11S 1.398(6) . ?
C10S N2S 1.420(7) . ?
C11S F7S 1.332(5) . ?
C11S C12S 1.366(6) . ?
C12S F8S 1.346(5) . ?
N1S N2S 1.211(7) . ?
I1S C1T 2.084(3) . ?
I2S C7T 2.085(3) . ?
C1T C2T 1.3731 . ?
C1T C6T 1.3761 . ?
C2T F1T 1.3459 . ?
C2T C3T 1.3771 . ?
C3T F2T 1.3380 . ?
C3T C4T 1.3899 . ?
C4T C5T 1.3935 . ?
C4T N1T 1.4151 . ?
C5T F3T 1.3363 . ?
C5T C6T 1.3687 . ?
C6T F4T 1.3450 . ?
C7T C8T 1.3721 . ?
C7T C12T 1.3734 . ?
C8T F5T 1.3453 . ?
C8T C9T 1.3752 . ?
C9T F6T 1.3370 . ?
C9T C10T 1.3900 . ?
C10T C11T 1.3935 . ?
C10T N2T 1.4138 . ?
C11T F7T 1.3359 . ?
C11T C12T 1.3695 . ?
C12T F8T 1.3447 . ?
N1T N2T 1.1937 . ?

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 C10A 107.7(6) . . ?
C2A C1A H1A 126.2 . . ?
C10A C1A H1A 126.2 . . ?
C3A C2A C1A 110.8(7) . . ?
C3A C2A H2A 124.6 . . ?
C1A C2A H2A 124.6 . . ?
C4A C3A C2A 108.0(6) . . ?
C4A C3A H3A 126.0 . . ?
C2A C3A H3A 126.0 . . ?
C5A C4A C3A 125.2(6) . . ?
C5A C4A C10A 128.1(5) . . ?
C3A C4A C10A 106.7(5) . . ?
C6A C5A C4A 128.2(7) . . ?
C6A C5A H5A 115.9 . . ?
C4A C5A H5A 115.9 . . ?
C5A C6A C7A 129.8(8) . . ?
C5A C6A H6A 115.1 . . ?
C7A C6A H6A 115.1 . . ?
C6A C7A C8A 128.6(9) . . ?
C6A C7A H7A 115.7 . . ?
C8A C7A H7A 115.7 . . ?
C9A C8A C7A 130.0(8) . . ?
C9A C8A H8A 115.0 . . ?
C7A C8A H8A 115.0 . . ?
C10A C9A C8A 128.7(7) . . ?
C10A C9A H9A 115.6 . . ?
C8A C9A H9A 115.6 . . ?
C9A C10A C1A 126.4(6) . . ?
C9A C10A C4A 126.6(5) . . ?
C1A C10A C4A 106.7(5) . . ?
C2C C1C C10C 108.1(7) . . ?
C2C C1C H1C 126.0 . . ?
C10C C1C H1C 126.0 . . ?
C1C C2C C3C 110.7(8) . . ?
C1C C2C H2C 124.7 . . ?
C3C C2C H2C 124.7 . . ?
C4C C3C C2C 107.9(7) . . ?
C4C C3C H3C 126.0 . . ?
C2C C3C H3C 126.0 . . ?
C5C C4C C3C 126.1(7) . . ?
C5C C4C C10C 127.0(7) . . ?
C3C C4C C10C 106.8(5) . . ?
C4C C5C C6C 128.1(9) . . ?
C4C C5C H5C 115.9 . . ?
C6C C5C H5C 115.9 . . ?
C5C C6C C7C 130.8(11) . . ?
C5C C6C H6C 114.6 . . ?
C7C C6C H6C 114.6 . . ?
C6C C7C C8C 127.4(12) . . ?
C6C C7C H7C 116.3 . . ?
C8C C7C H7C 116.3 . . ?
C9C C8C C7C 129.9(11) . . ?
C9C C8C H8C 115.1 . . ?
C7C C8C H8C 115.1 . . ?
C10C C9C C8C 128.9(9) . . ?
C10C C9C H9C 115.5 . . ?
C8C C9C H9C 115.5 . . ?
C9C C10C C1C 125.9(8) . . ?
C9C C10C C4C 127.2(7) . . ?
C1C C10C C4C 106.5(5) . . ?
C10B C1B C2B 108.0(7) . . ?
C10B C1B H1B 126.0 . . ?
C2B C1B H1B 126.0 . . ?
C3B C2B C1B 110.7(8) . . ?
C3B C2B H2B 124.6 . . ?
C1B C2B H2B 124.6 . . ?
C4B C3B C2B 107.9(7) . . ?
C4B C3B H3B 126.1 . . ?
C2B C3B H3B 126.1 . . ?
C5B C4B C3B 126.2(7) . . ?
C5B C4B C10B 127.0(6) . . ?
C3B C4B C10B 106.7(5) . . ?
C4B C5B C6B 128.9(7) . . ?
C4B C5B H5B 115.6 . . ?
C6B C5B H5B 115.6 . . ?
C5B C6B C7B 130.0(10) . . ?
C5B C6B H6B 115.0 . . ?
C7B C6B H6B 115.0 . . ?
C6B C7B C8B 128.3(10) . . ?
C6B C7B H7B 115.8 . . ?
C8B C7B H7B 115.8 . . ?
C9B C8B C7B 129.6(9) . . ?
C9B C8B H8B 115.2 . . ?
C7B C8B H8B 115.2 . . ?
C10B C9B C8B 129.1(8) . . ?
C10B C9B H9B 115.5 . . ?
C8B C9B H9B 115.5 . . ?
C9B C10B C1B 126.3(7) . . ?
C9B C10B C4B 127.1(6) . . ?
C1B C10B C4B 106.6(5) . . ?
C6S C1S C2S 117.8(4) . . ?
C6S C1S I1S 121.0(3) . . ?
C2S C1S I1S 121.2(3) . . ?
F1S C2S C3S 118.4(4) . . ?
F1S C2S C1S 119.9(4) . . ?
C3S C2S C1S 121.7(4) . . ?
F2S C3S C2S 117.4(4) . . ?
F2S C3S C4S 121.6(4) . . ?
C2S C3S C4S 120.9(4) . . ?
C3S C4S C5S 116.6(5) . . ?
C3S C4S N1S 128.2(4) . . ?
C5S C4S N1S 115.2(4) . . ?
F3S C5S C6S 118.7(4) . . ?
F3S C5S C4S 119.5(4) . . ?
C6S C5S C4S 121.9(4) . . ?
F4S C6S C5S 119.0(4) . . ?
F4S C6S C1S 119.9(4) . . ?
C5S C6S C1S 121.1(4) . . ?
C8S C7S C12S 117.5(4) . . ?
C8S C7S I2S 121.5(3) . . ?
C12S C7S I2S 121.1(3) . . ?
F5S C8S C7S 119.9(4) . . ?
F5S C8S C9S 118.3(4) . . ?
C7S C8S C9S 121.8(4) . . ?
F6S C9S C8S 117.5(4) . . ?
F6S C9S C10S 121.4(4) . . ?
C8S C9S C10S 121.1(4) . . ?
C9S C10S C11S 116.3(5) . . ?
C9S C10S N2S 129.0(4) . . ?
C11S C10S N2S 114.7(4) . . ?
F7S C11S C12S 119.2(4) . . ?
F7S C11S C10S 119.0(4) . . ?
C12S C11S C10S 121.8(5) . . ?
F8S C12S C11S 118.1(4) . . ?
F8S C12S C7S 120.4(4) . . ?
C11S C12S C7S 121.5(4) . . ?
N2S N1S C4S 115.9(5) . . ?
N1S N2S C10S 115.7(5) . . ?
C2T C1T C6T 117.2 . . ?
C2T C1T I1S 122.0(4) . . ?
C6T C1T I1S 120.8(4) . . ?
F1T C2T C1T 120.2 . . ?
F1T C2T C3T 117.9 . . ?
C1T C2T C3T 121.9 . . ?
F2T C3T C2T 118.5 . . ?
F2T C3T C4T 120.3 . . ?
C2T C3T C4T 121.2 . . ?
C3T C4T C5T 116.3 . . ?
C3T C4T N1T 123.7 . . ?
C5T C4T N1T 120.0 . . ?
F3T C5T C6T 118.6 . . ?
F3T C5T C4T 119.7 . . ?
C6T C5T C4T 121.7 . . ?
F4T C6T C5T 118.8 . . ?
F4T C6T C1T 119.6 . . ?
C5T C6T C1T 121.6 . . ?
C8T C7T C12T 117.9 . . ?
C8T C7T I2S 121.3(4) . . ?
C12T C7T I2S 120.8(4) . . ?
F5T C8T C7T 119.9 . . ?
F5T C8T C9T 118.5 . . ?
C7T C8T C9T 121.6 . . ?
F6T C9T C8T 117.6 . . ?
F6T C9T C10T 121.3 . . ?
C8T C9T C10T 121.0 . . ?
C9T C10T C11T 116.7 . . ?
C9T C10T N2T 123.4 . . ?
C11T C10T N2T 119.9 . . ?
F7T C11T C12T 117.9 . . ?
F7T C11T C10T 120.6 . . ?
C12T C11T C10T 121.5 . . ?
F8T C12T C11T 118.9 . . ?
F8T C12T C7T 119.9 . . ?
C11T C12T C7T 121.2 . . ?
N2T N1T C4T 119.1 . . ?
N1T N2T C10T 119.4 . . ?

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
C10A C1A C2A C3A 2.4(5) . . . . ?
C1A C2A C3A C4A -2.1(5) . . . . ?
C2A C3A C4A C5A 178.0(8) . . . . ?
C2A C3A C4A C10A 1.0(8) . . . . ?
C3A C4A C5A C6A -176.2(11) . . . . ?
C10A C4A C5A C6A 0.3(17) . . . . ?
C4A C5A C6A C7A 1.0(19) . . . . ?
C5A C6A C7A C8A -1.2(19) . . . . ?
C6A C7A C8A C9A 1(2) . . . . ?
C7A C8A C9A C10A -2.1(19) . . . . ?
C8A C9A C10A C1A 176.2(11) . . . . ?
C8A C9A C10A C4A 2.7(16) . . . . ?
C2A C1A C10A C9A -176.2(8) . . . . ?
C2A C1A C10A C4A -1.7(8) . . . . ?
C5A C4A C10A C9A -2.0(15) . . . . ?
C3A C4A C10A C9A 174.9(9) . . . . ?
C5A C4A C10A C1A -176.5(9) . . . . ?
C3A C4A C10A C1A 0.4(10) . . . . ?
C10C C1C C2C C3C -2.6(8) . . . . ?
C1C C2C C3C C4C 1.2(8) . . . . ?
C2C C3C C4C C5C -176.1(14) . . . . ?
C2C C3C C4C C10C 0.6(13) . . . . ?
C3C C4C C5C C6C -178.0(19) . . . . ?
C10C C4C C5C C6C 6(3) . . . . ?
C4C C5C C6C C7C -10(3) . . . . ?
C5C C6C C7C C8C 6(4) . . . . ?
C6C C7C C8C C9C -3(3) . . . . ?
C7C C8C C9C C10C 5(3) . . . . ?
C8C C9C C10C C1C -177.5(19) . . . . ?
C8C C9C C10C C4C -7(3) . . . . ?
C2C C1C C10C C9C 175.3(13) . . . . ?
C2C C1C C10C C4C 2.8(13) . . . . ?
C5C C4C C10C C9C 2(3) . . . . ?
C3C C4C C10C C9C -174.5(15) . . . . ?
C5C C4C C10C C1C 174.5(16) . . . . ?
C3C C4C C10C C1C -2.1(16) . . . . ?
C10B C1B C2B C3B 0.1(7) . . . . ?
C1B C2B C3B C4B -0.7(7) . . . . ?
C2B C3B C4B C5B 179.3(10) . . . . ?
C2B C3B C4B C10B 1.0(10) . . . . ?
C3B C4B C5B C6B -178.2(18) . . . . ?
C10B C4B C5B C6B 0(2) . . . . ?
C4B C5B C6B C7B -1(3) . . . . ?
C5B C6B C7B C8B 2(3) . . . . ?
C6B C7B C8B C9B -1(3) . . . . ?
C7B C8B C9B C10B 0(3) . . . . ?
C8B C9B C10B C1B -179.9(18) . . . . ?
C8B C9B C10B C4B 0(2) . . . . ?
C2B C1B C10B C9B -179.6(10) . . . . ?
C2B C1B C10B C4B 0.5(10) . . . . ?
C5B C4B C10B C9B 0.8(18) . . . . ?
C3B C4B C10B C9B 179.1(12) . . . . ?
C5B C4B C10B C1B -179.2(12) . . . . ?
C3B C4B C10B C1B -0.9(11) . . . . ?
C6S C1S C2S F1S -179.0(5) . . . . ?
I1S C1S C2S F1S 0.9(8) . . . . ?
C6S C1S C2S C3S 0.1(9) . . . . ?
I1S C1S C2S C3S -180.0(5) . . . . ?
F1S C2S C3S F2S 0.0(9) . . . . ?
C1S C2S C3S F2S -179.2(6) . . . . ?
F1S C2S C3S C4S 178.6(5) . . . . ?
C1S C2S C3S C4S -0.5(10) . . . . ?
F2S C3S C4S C5S 179.3(6) . . . . ?
C2S C3S C4S C5S 0.7(9) . . . . ?
F2S C3S C4S N1S -1.0(10) . . . . ?
C2S C3S C4S N1S -179.6(6) . . . . ?
C3S C4S C5S F3S 179.4(5) . . . . ?
N1S C4S C5S F3S -0.3(8) . . . . ?
C3S C4S C5S C6S -0.6(9) . . . . ?
N1S C4S C5S C6S 179.7(6) . . . . ?
F3S C5S C6S F4S 0.4(9) . . . . ?
C4S C5S C6S F4S -179.5(6) . . . . ?
F3S C5S C6S C1S -179.8(5) . . . . ?
C4S C5S C6S C1S 0.2(10) . . . . ?
C2S C1S C6S F4S 179.8(5) . . . . ?
I1S C1S C6S F4S -0.1(8) . . . . ?
C2S C1S C6S C5S 0.0(9) . . . . ?
I1S C1S C6S C5S -179.9(5) . . . . ?
C12S C7S C8S F5S 178.6(6) . . . . ?
I2S C7S C8S F5S -1.7(9) . . . . ?
C12S C7S C8S C9S 0.1(10) . . . . ?
I2S C7S C8S C9S 179.8(5) . . . . ?
F5S C8S C9S F6S 0.3(9) . . . . ?
C7S C8S C9S F6S 178.9(6) . . . . ?
F5S C8S C9S C10S -178.8(6) . . . . ?
C7S C8S C9S C10S -0.3(10) . . . . ?
F6S C9S C10S C11S -178.7(6) . . . . ?
C8S C9S C10S C11S 0.4(9) . . . . ?
F6S C9S C10S N2S -0.1(11) . . . . ?
C8S C9S C10S N2S 179.0(6) . . . . ?
C9S C10S C11S F7S 179.9(5) . . . . ?
N2S C10S C11S F7S 1.1(8) . . . . ?
C9S C10S C11S C12S -0.4(9) . . . . ?
N2S C10S C11S C12S -179.2(6) . . . . ?
F7S C11S C12S F8S 0.8(9) . . . . ?
C10S C11S C12S F8S -178.9(6) . . . . ?
F7S C11S C12S C7S 179.9(5) . . . . ?
C10S C11S C12S C7S 0.3(10) . . . . ?
C8S C7S C12S F8S 179.0(6) . . . . ?
I2S C7S C12S F8S -0.7(8) . . . . ?
C8S C7S C12S C11S -0.1(9) . . . . ?
I2S C7S C12S C11S -179.8(5) . . . . ?
C3S C4S N1S N2S -4.9(10) . . . . ?
C5S C4S N1S N2S 174.8(6) . . . . ?
C4S N1S N2S C10S 178.6(5) . . . . ?
C9S C10S N2S N1S 6.8(10) . . . . ?
C11S C10S N2S N1S -174.6(6) . . . . ?
C6T C1T C2T F1T -179.6 . . . . ?
I1S C1T C2T F1T 1.8(9) . . . . ?
C6T C1T C2T C3T -0.2 . . . . ?
I1S C1T C2T C3T -178.8(9) . . . . ?
F1T C2T C3T F2T 0.0 . . . . ?
C1T C2T C3T F2T -179.4 . . . . ?
F1T C2T C3T C4T 178.9 . . . . ?
C1T C2T C3T C4T -0.6 . . . . ?
F2T C3T C4T C5T 179.6 . . . . ?
C2T C3T C4T C5T 0.8 . . . . ?
F2T C3T C4T N1T -1.7 . . . . ?
C2T C3T C4T N1T 179.5 . . . . ?
C3T C4T C5T F3T 179.6 . . . . ?
N1T C4T C5T F3T 0.8 . . . . ?
C3T C4T C5T C6T -0.3 . . . . ?
N1T C4T C5T C6T -179.1 . . . . ?
F3T C5T C6T F4T 0.3 . . . . ?
C4T C5T C6T F4T -179.8 . . . . ?
F3T C5T C6T C1T 179.7 . . . . ?
C4T C5T C6T C1T -0.5 . . . . ?
C2T C1T C6T F4T -179.9 . . . . ?
I1S C1T C6T F4T -1.3(9) . . . . ?
C2T C1T C6T C5T 0.7 . . . . ?
I1S C1T C6T C5T 179.3(9) . . . . ?
C12T C7T C8T F5T -179.8 . . . . ?
I2S C7T C8T F5T 1.3(9) . . . . ?
C12T C7T C8T C9T -0.9 . . . . ?
I2S C7T C8T C9T -179.9(9) . . . . ?
F5T C8T C9T F6T -1.4 . . . . ?
C7T C8T C9T F6T 179.7 . . . . ?
F5T C8T C9T C10T 179.7 . . . . ?
C7T C8T C9T C10T 0.8 . . . . ?
F6T C9T C10T C11T -178.9 . . . . ?
C8T C9T C10T C11T 0.0 . . . . ?
F6T C9T C10T N2T 0.4 . . . . ?
C8T C9T C10T N2T 179.2 . . . . ?
C9T C10T C11T F7T 179.9 . . . . ?
N2T C10T C11T F7T 0.6 . . . . ?
C9T C10T C11T C12T -0.7 . . . . ?
N2T C10T C11T C12T -180.0 . . . . ?
F7T C11T C12T F8T -0.2 . . . . ?
C10T C11T C12T F8T -179.6 . . . . ?
F7T C11T C12T C7T -180.0 . . . . ?
C10T C11T C12T C7T 0.6 . . . . ?
C8T C7T C12T F8T -179.6 . . . . ?
I2S C7T C12T F8T -0.6(9) . . . . ?
C8T C7T C12T C11T 0.2 . . . . ?
I2S C7T C12T C11T 179.2(9) . . . . ?
C3T C4T N1T N2T 1.0 . . . . ?
C5T C4T N1T N2T 179.7 . . . . ?
C4T N1T N2T C10T 179.3 . . . . ?
C9T C10T N2T N1T 0.3 . . . . ?
C11T C10T N2T N1T 179.5 . . . . ?

_refine_diff_density_max         1.180
_refine_diff_density_min         -1.038
_refine_diff_density_rms         0.105

####################################################################### 
# 
# 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_azu_14tfib_1-2_253K
_database_code_depnum_ccdc_archive 'CCDC 2000773'
loop_
_audit_author_name
_audit_author_address
'Filip Topic'
;McGill University
Canada
;
_audit_update_record             
;
2020-05-03 deposited with the CCDC.	2020-11-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_formula_moiety         '2(C6 F4 I2), C10 H8'
_chemical_formula_sum            'C22 H8 F8 I4'
_chemical_formula_weight         931.88

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   5.9541(4)
_cell_length_b                   9.6644(7)
_cell_length_c                   11.8639(9)
_cell_angle_alpha                67.331(2)
_cell_angle_beta                 85.205(3)
_cell_angle_gamma                80.816(2)
_cell_volume                     621.68(8)
_cell_formula_units_Z            1
_cell_measurement_temperature    253.0(1)
_cell_measurement_reflns_used    5001
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      31.15

_exptl_crystal_description       plate
_exptl_crystal_colour            blue
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.489
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.185
_exptl_crystal_size_mid          0.159
_exptl_crystal_size_min          0.089
_exptl_absorpt_coefficient_mu    5.081
_shelx_estimated_absorpt_T_min   0.453
_shelx_estimated_absorpt_T_max   0.661
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5619
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_process_details   
'SADABS-2016/2 (Krause, Herbst-Irmer, Sheldrick & Stalke, 2015)'

_diffrn_ambient_temperature      253.0(1)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Incoatec Microfocus X-ray Source I\mS (Mo)'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'Bruker D8 Venture, Dual, Cu at zero, PHOTON II'
_diffrn_detector                 CPAD
_diffrn_detector_type            'PHOTON II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            11276
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.306
_diffrn_reflns_theta_max         31.199
_diffrn_reflns_theta_full        25.250
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             4012
_reflns_number_gt                2646
_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       'Bruker APEX3'
_computing_cell_refinement       'Bruker APEX3'
_computing_data_reduction        'Bruker APEX3'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_publication_material  
'OLEX2 (Dolomanov et al., 2009) & WinGX (Farrugia, 2012)'

_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)+(0.0139P)²+1.6245P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick, 2015)'
_refine_ls_extinction_coef       0.0062(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4012
_refine_ls_number_parameters     200
_refine_ls_number_restraints     182
_refine_ls_R_factor_all          0.0708
_refine_ls_R_factor_gt           0.0391
_refine_ls_wR_factor_ref         0.0774
_refine_ls_wR_factor_gt          0.0670
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.004
_refine_ls_shift/su_max          0.001
_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 0.171(2) 0.0866(14) 0.1097(14) 0.056(4) Uani 0.5 1 d D U P A -1
H1A H 0.303749 0.064779 0.153346 0.067 Uiso 0.5 1 calc R U P A -1
C2A C 0.002(2) 0.2087(15) 0.0957(14) 0.063(5) Uani 0.5 1 d D U P A -1
H2A H 0.003561 0.281463 0.128874 0.076 Uiso 0.5 1 calc R U P A -1
C3A C -0.172(2) 0.2059(13) 0.0245(13) 0.055(4) Uani 0.5 1 d D U P A -1
H3A H -0.303271 0.275628 0.002785 0.065 Uiso 0.5 1 calc R U P A -1
C4A C -0.1143(11) 0.0805(7) -0.0087(6) 0.0388(15) Uani 0.5 1 d D U P A -1
C5A C -0.2435(13) 0.0390(9) -0.0785(7) 0.0490(18) Uani 0.5 1 d D U P A -1
H5A H -0.380466 0.101071 -0.104982 0.059 Uiso 0.5 1 calc R U P A -1
C6A C -0.195(2) -0.0832(14) -0.1142(14) 0.053(4) Uani 0.5 1 d D U P A -1
H6A H -0.303989 -0.091365 -0.162278 0.064 Uiso 0.5 1 calc R U P A -1
C7A C -0.0088(19) -0.1949(15) -0.0890(14) 0.056(4) Uani 0.5 1 d D U P A -1
H7A H -0.010110 -0.267255 -0.122615 0.068 Uiso 0.5 1 calc R U P A -1
C8A C 0.180(2) -0.2142(15) -0.0205(15) 0.057(4) Uani 0.5 1 d D U P A -1
H8A H 0.286806 -0.298015 -0.014706 0.068 Uiso 0.5 1 calc R U P A -1
C9A C 0.2331(14) -0.1274(8) 0.0403(8) 0.051(2) Uani 0.5 1 d D U P A -1
H9A H 0.369374 -0.161090 0.081761 0.061 Uiso 0.5 1 calc R U P A -1
C10A C 0.1100(11) 0.0023(7) 0.0473(6) 0.0413(16) Uani 0.5 1 d D U P A -1
C1S C 0.3893(6) 0.2133(4) 0.5104(3) 0.0380(8) Uani 1 1 d . . . . .
C2S C 0.5594(7) 0.2769(5) 0.5358(4) 0.0417(9) Uani 1 1 d . . . . .
C3S C 0.6780(7) 0.3769(5) 0.4431(4) 0.0463(10) Uani 1 1 d . . . . .
C4S C 0.6294(7) 0.4173(4) 0.3224(4) 0.0437(9) Uani 1 1 d . . . . .
C5S C 0.4588(7) 0.3533(5) 0.2971(4) 0.0449(9) Uani 1 1 d . . . . .
C6S C 0.3411(6) 0.2534(4) 0.3897(4) 0.0417(9) Uani 1 1 d . . . . .
F1S F 0.6134(5) 0.2440(3) 0.6516(2) 0.0653(7) Uani 1 1 d . . . . .
F2S F 0.8420(5) 0.4358(3) 0.4736(3) 0.0727(8) Uani 1 1 d . . . . .
F3S F 0.4057(5) 0.3863(4) 0.1809(2) 0.0704(8) Uani 1 1 d . . . . .
F4S F 0.1768(5) 0.1948(4) 0.3598(3) 0.0682(8) Uani 1 1 d . . . . .
I1S I 0.20897(5) 0.06530(3) 0.65008(3) 0.05753(13) Uani 1 1 d . . . . .
I2S I 0.80514(6) 0.56998(3) 0.18392(3) 0.06837(15) 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 1.392(7) . ?
C1A C10A 1.397(7) . ?
C1A H1A 0.9300 . ?
C2A C3A 1.399(7) . ?
C2A H2A 0.9300 . ?
C3A C4A 1.397(7) . ?
C3A H3A 0.9300 . ?
C4A C5A 1.378(6) . ?
C4A C10A 1.495(7) . ?
C5A C6A 1.384(7) . ?
C5A H5A 0.9300 . ?
C6A C7A 1.382(7) . ?
C6A H6A 0.9300 . ?
C7A C8A 1.389(7) . ?
C7A H7A 0.9300 . ?
C8A C9A 1.383(7) . ?
C8A H8A 0.9300 . ?
C9A C10A 1.376(6) . ?
C9A H9A 0.9300 . ?
C1S C2S 1.374(5) . ?
C1S C6S 1.375(6) . ?
C1S I1S 2.076(4) . ?
C2S F1S 1.339(5) . ?
C2S C3S 1.382(6) . ?
C3S F2S 1.343(5) . ?
C3S C4S 1.374(6) . ?
C4S C5S 1.378(6) . ?
C4S I2S 2.076(4) . ?
C5S F3S 1.342(5) . ?
C5S C6S 1.379(5) . ?
C6S F4S 1.339(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2A C1A C10A 108.7(9) . . ?
C2A C1A H1A 125.6 . . ?
C10A C1A H1A 125.6 . . ?
C1A C2A C3A 109.9(11) . . ?
C1A C2A H2A 125.0 . . ?
C3A C2A H2A 125.0 . . ?
C4A C3A C2A 108.5(9) . . ?
C4A C3A H3A 125.8 . . ?
C2A C3A H3A 125.8 . . ?
C5A C4A C3A 125.7(7) . . ?
C5A C4A C10A 127.8(5) . . ?
C3A C4A C10A 106.5(5) . . ?
C4A C5A C6A 128.2(7) . . ?
C4A C5A H5A 115.9 . . ?
C6A C5A H5A 115.9 . . ?
C7A C6A C5A 129.6(11) . . ?
C7A C6A H6A 115.2 . . ?
C5A C6A H6A 115.2 . . ?
C6A C7A C8A 129.0(12) . . ?
C6A C7A H7A 115.5 . . ?
C8A C7A H7A 115.5 . . ?
C9A C8A C7A 129.7(11) . . ?
C9A C8A H8A 115.2 . . ?
C7A C8A H8A 115.2 . . ?
C10A C9A C8A 128.2(7) . . ?
C10A C9A H9A 115.9 . . ?
C8A C9A H9A 115.9 . . ?
C9A C10A C1A 126.2(7) . . ?
C9A C10A C4A 127.4(5) . . ?
C1A C10A C4A 106.4(5) . . ?
C2S C1S C6S 117.5(3) . . ?
C2S C1S I1S 120.9(3) . . ?
C6S C1S I1S 121.6(3) . . ?
F1S C2S C1S 120.6(4) . . ?
F1S C2S C3S 118.4(4) . . ?
C1S C2S C3S 121.1(4) . . ?
F2S C3S C4S 120.2(4) . . ?
F2S C3S C2S 118.3(4) . . ?
C4S C3S C2S 121.4(4) . . ?
C3S C4S C5S 117.5(4) . . ?
C3S C4S I2S 121.2(3) . . ?
C5S C4S I2S 121.4(3) . . ?
F3S C5S C4S 120.4(4) . . ?
F3S C5S C6S 118.6(4) . . ?
C4S C5S C6S 121.0(4) . . ?
F4S C6S C1S 120.0(3) . . ?
F4S C6S C5S 118.5(4) . . ?
C1S C6S C5S 121.5(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
C10A C1A C2A C3A 0.0(7) . . . . ?
C1A C2A C3A C4A -0.1(7) . . . . ?
C2A C3A C4A C5A 179.7(7) . . . . ?
C2A C3A C4A C10A 0.2(8) . . . . ?
C3A C4A C5A C6A 179.9(15) . . . . ?
C10A C4A C5A C6A -0.7(16) . . . . ?
C4A C5A C6A C7A 0.6(19) . . . . ?
C5A C6A C7A C8A 0.1(19) . . . . ?
C6A C7A C8A C9A -0.2(19) . . . . ?
C7A C8A C9A C10A 0(2) . . . . ?
C8A C9A C10A C1A -179.7(16) . . . . ?
C8A C9A C10A C4A 0.8(16) . . . . ?
C2A C1A C10A C9A -179.5(7) . . . . ?
C2A C1A C10A C4A 0.1(8) . . . . ?
C5A C4A C10A C9A 0.0(13) . . . . ?
C3A C4A C10A C9A 179.4(10) . . . . ?
C5A C4A C10A C1A -179.7(10) . . . . ?
C3A C4A C10A C1A -0.2(9) . . . . ?
C6S C1S C2S F1S 179.3(4) . . . . ?
I1S C1S C2S F1S 0.4(5) . . . . ?
C6S C1S C2S C3S -0.3(6) . . . . ?
I1S C1S C2S C3S -179.2(3) . . . . ?
F1S C2S C3S F2S 0.2(6) . . . . ?
C1S C2S C3S F2S 179.8(4) . . . . ?
F1S C2S C3S C4S -179.1(4) . . . . ?
C1S C2S C3S C4S 0.5(6) . . . . ?
F2S C3S C4S C5S -179.8(4) . . . . ?
C2S C3S C4S C5S -0.6(6) . . . . ?
F2S C3S C4S I2S -0.2(5) . . . . ?
C2S C3S C4S I2S 179.1(3) . . . . ?
C3S C4S C5S F3S -178.9(4) . . . . ?
I2S C4S C5S F3S 1.4(5) . . . . ?
C3S C4S C5S C6S 0.4(6) . . . . ?
I2S C4S C5S C6S -179.2(3) . . . . ?
C2S C1S C6S F4S -179.9(4) . . . . ?
I1S C1S C6S F4S -1.0(5) . . . . ?
C2S C1S C6S C5S 0.2(6) . . . . ?
I1S C1S C6S C5S 179.1(3) . . . . ?
F3S C5S C6S F4S -0.8(6) . . . . ?
C4S C5S C6S F4S 179.9(4) . . . . ?
F3S C5S C6S C1S 179.1(4) . . . . ?
C4S C5S C6S C1S -0.2(6) . . . . ?

_refine_diff_density_max         1.421
_refine_diff_density_min         -1.473
_refine_diff_density_rms         0.095

