# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_k14040
_database_code_depnum_ccdc_archive 'CCDC 1482195'
# CIF edited on-the-fly by script CIFFIX (S. Parkin, 2000-2014). 
# CIFFIX: http://xray.uky.edu/people/parkin/programs/ciffix 
_audit_update_record             
;
2016-05-26 deposited with the CCDC.	2020-05-29 downloaded from the CCDC.
;

_audit_creation_method           'SHELXL-2014/7 and CIFFIX'

_shelx_SHELXL_version_number     2014/7

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H11 F6 N S'
_chemical_formula_sum            'C16 H11 F6 N S'
_chemical_formula_weight         363.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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'

_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                   7.8034(2)
_cell_length_b                   13.0620(3)
_cell_length_c                   14.6101(4)
_cell_angle_alpha                91.3974(10)
_cell_angle_beta                 92.4383(11)
_cell_angle_gamma                92.1014(10)
_cell_volume                     1486.33(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    90.0(2)
_cell_measurement_reflns_used    6693
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      27.48

_exptl_crystal_description       'solvent-rounded tablet'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.624
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.025
_exptl_absorpt_coefficient_mu    0.283
_shelx_estimated_absorpt_T_min   0.920
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.753
_exptl_absorpt_correction_T_max  0.962
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_special_details   
; 
In addition to absorption, multi-scan techniques also correct other slowly 
varying changes in scale factor over reciprocal space, such as those caused 
by x-ray beam inhomogeneity, goniometer imperfection, crystal decomposition, 
crystal longer than the x-ray beam cross section, absorption by the crystal 
mount etc.  These account, by and large, for much of the difference between 
estimated values of Tmin and Tmax and the _exptl_absorpt_correction_ values. 
;

_exptl_special_details           
; 
The crystal was mounted with polyisobutene oil on the tip of a fine glass 
fibre, which was fastened in a copper mounting pin with electrical solder. 
It was placed directly into the cold gas stream of a liquid nitrogen based 
cryostat, according to published methods (Hope, 1994; Parkin & Hope, 1998). 
 
Diffraction data were collected with the crystal at 90K, which is standard 
practice in this laboratory for the majority of flash-cooled crystals. 

This crystal was a minor-component polymorph.  The major component was 
orthorhombic (probably Pnma or Pna21), with similar cell axes to this 
triclinic variant.  The orthorhombic crystals underwent a destructive 
phase transition on cooling below room temperature. That structure was 
solved, but there was a lot of diffuse scatter in the diffraction pattern, 
and refinement was unsatisfactory.  The triclinic crystals modelled here 
had none of the problems associated with the orthorhombic allomorph.
;

_diffrn_ambient_temperature      90.0(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed-tube'
_diffrn_measurement_device_type  'Nonius KappaCCD diffractometer'
_diffrn_measurement_method       'φ and ω scans at fixed χ = 55°'
_diffrn_detector_area_resol_mean 9.1
_diffrn_reflns_number            50797
_diffrn_reflns_av_unetI/netI     0.0549
_diffrn_reflns_av_R_equivalents  0.0622
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.395
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000

_reflns_number_total             6808
_reflns_number_gt                4446
_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       'COLLECT (Nonius, 1998)'
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 2006)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 2006)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015b)'
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material  
'SHELX (Sheldrick, 2008) and CIFFIX (Parkin, 2013)'

_refine_special_details          
; 
Refinement progress was checked using Platon (Spek, 2009) and by 
an R-tensor (Parkin, 2000). The final model was further checked 
with the IUCr utility checkCIF. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0546P)²+2.3134P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6808
_refine_ls_number_parameters     433
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1035
_refine_ls_R_factor_gt           0.0576
_refine_ls_wR_factor_ref         0.1538
_refine_ls_wR_factor_gt          0.1325
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_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
N1A N 1.0934(3) 0.16135(18) 0.25392(16) 0.0226(5) Uani 1 1 d . . . . .
S1A S 1.0415(1) 0.39062(6) 0.25591(5) 0.02626(19) Uani 1 1 d . . . . .
F1A F 0.8486(4) 0.27291(16) 0.65405(15) 0.0640(8) Uani 1 1 d . . . . .
F2A F 1.0601(3) 0.38014(18) 0.63898(15) 0.0550(6) Uani 1 1 d . . . . .
F3A F 0.8101(3) 0.41496(16) 0.58901(13) 0.0446(5) Uani 1 1 d . . . . .
F4A F 0.8063(3) 0.26026(16) -0.14972(14) 0.0565(7) Uani 1 1 d . . . . .
F5A F 0.9722(3) 0.38935(18) -0.11652(15) 0.0569(7) Uani 1 1 d . . . . .
F6A F 0.7137(3) 0.38675(19) -0.07560(15) 0.0584(7) Uani 1 1 d . . . . .
C1A C 1.0482(4) 0.2038(2) 0.3386(2) 0.0241(6) Uani 1 1 d . . . . .
C2A C 1.0423(4) 0.1453(2) 0.4173(2) 0.0261(7) Uani 1 1 d . . . . .
H2AA H 1.0697 0.0750 0.4139 0.031 Uiso 1 1 calc R U . . .
C3A C 0.9972(4) 0.1880(2) 0.4999(2) 0.0305(7) Uani 1 1 d . . . . .
H3AA H 0.9957 0.1471 0.5528 0.037 Uiso 1 1 calc R U . . .
C4A C 0.9544(4) 0.2894(2) 0.5066(2) 0.0274(7) Uani 1 1 d . . . . .
C5A C 0.9586(4) 0.3490(2) 0.4288(2) 0.0261(7) Uani 1 1 d . . . . .
H5AA H 0.9266 0.4184 0.4322 0.031 Uiso 1 1 calc R U . . .
C6A C 1.0091(4) 0.3077(2) 0.3468(2) 0.0232(6) Uani 1 1 d . . . . .
C7A C 0.9169(5) 0.3381(2) 0.5974(2) 0.0330(8) Uani 1 1 d . . . . .
C8A C 0.9913(4) 0.3049(2) 0.1639(2) 0.0221(6) Uani 1 1 d . . . . .
C9A C 0.9263(4) 0.3441(2) 0.0825(2) 0.0261(7) Uani 1 1 d . . . . .
H9AA H 0.8969 0.4139 0.0803 0.031 Uiso 1 1 calc R U . . .
C10A C 0.9041(4) 0.2817(2) 0.0045(2) 0.0260(7) Uani 1 1 d . . . . .
C11A C 0.9424(4) 0.1796(2) 0.0091(2) 0.0277(7) Uani 1 1 d . . . . .
H11A H 0.9282 0.1367 -0.0442 0.033 Uiso 1 1 calc R U . . .
C12A C 1.0018(4) 0.1389(2) 0.0916(2) 0.0267(7) Uani 1 1 d . . . . .
H12A H 1.0245 0.0680 0.0940 0.032 Uiso 1 1 calc R U . . .
C13A C 1.0283(4) 0.2007(2) 0.17016(19) 0.0222(6) Uani 1 1 d . . . . .
C14A C 0.8482(4) 0.3285(2) -0.0850(2) 0.0299(7) Uani 1 1 d . . . . .
C15A C 1.1633(4) 0.0582(2) 0.2523(2) 0.0266(7) Uani 1 1 d . . . . .
H15A H 1.2442 0.0528 0.3059 0.032 Uiso 1 1 calc R U . . .
H15B H 1.2299 0.0504 0.1965 0.032 Uiso 1 1 calc R U . . .
C16A C 1.0300(4) -0.0307(2) 0.2537(2) 0.0298(7) Uani 1 1 d . . . . .
H16A H 1.0883 -0.0958 0.2524 0.045 Uiso 1 1 calc R U . . .
H16B H 0.9654 -0.0253 0.3095 0.045 Uiso 1 1 calc R U . . .
H16C H 0.9511 -0.0278 0.1999 0.045 Uiso 1 1 calc R U . . .
N1B N 0.5173(3) 0.37303(18) 0.26360(17) 0.0252(6) Uani 1 1 d . . . . .
S1B S 0.64236(10) 0.15800(6) 0.25940(5) 0.0275(2) Uani 1 1 d . . . . .
F1B F 0.2947(3) 0.19883(16) -0.13734(13) 0.0526(6) Uani 1 1 d . . . . .
F2B F 0.5240(3) 0.11522(19) -0.10856(15) 0.0557(6) Uani 1 1 d . . . . .
F3B F 0.2831(2) 0.06143(14) -0.06002(13) 0.0361(5) Uani 1 1 d . . . . .
F4B F 0.4389(4) 0.21466(19) 0.66961(15) 0.0756(9) Uani 1 1 d . . . . .
F5B F 0.5991(3) 0.09983(17) 0.61470(15) 0.0507(6) Uani 1 1 d . . . . .
F6B F 0.3274(3) 0.08527(17) 0.59145(16) 0.0525(6) Uani 1 1 d . . . . .
C1B C 0.4785(4) 0.3183(2) 0.1802(2) 0.0248(7) Uani 1 1 d . . . . .
C2B C 0.3930(4) 0.3625(2) 0.1064(2) 0.0271(7) Uani 1 1 d . . . . .
H2BA H 0.3557 0.4306 0.1127 0.033 Uiso 1 1 calc R U . . .
C3B C 0.3609(4) 0.3085(2) 0.0233(2) 0.0273(7) Uani 1 1 d . . . . .
H3BA H 0.3042 0.3401 -0.0268 0.033 Uiso 1 1 calc R U . . .
C4B C 0.4125(4) 0.2086(2) 0.0146(2) 0.0278(7) Uani 1 1 d . . . . .
C5B C 0.4934(4) 0.1626(2) 0.0884(2) 0.0274(7) Uani 1 1 d . . . . .
H5BA H 0.5250 0.0933 0.0829 0.033 Uiso 1 1 calc R U . . .
C6B C 0.5283(4) 0.2165(2) 0.1698(2) 0.0231(6) Uani 1 1 d . . . . .
C7B C 0.3791(4) 0.1479(3) -0.0733(2) 0.0313(7) Uani 1 1 d . . . . .
C8B C 0.5476(4) 0.2178(2) 0.3524(2) 0.0261(7) Uani 1 1 d . . . . .
C9B C 0.5334(4) 0.1656(2) 0.4330(2) 0.0288(7) Uani 1 1 d . . . . .
H9BA H 0.5652 0.0962 0.4355 0.035 Uiso 1 1 calc R U . . .
C10B C 0.4730(4) 0.2139(2) 0.5104(2) 0.0308(7) Uani 1 1 d . . . . .
C11B C 0.4185(4) 0.3136(3) 0.5048(2) 0.0305(7) Uani 1 1 d . . . . .
H11B H 0.3738 0.3463 0.5569 0.037 Uiso 1 1 calc R U . . .
C12B C 0.4290(4) 0.3657(2) 0.4235(2) 0.0261(7) Uani 1 1 d . . . . .
H12B H 0.3899 0.4336 0.4203 0.031 Uiso 1 1 calc R U . . .
C13B C 0.4961(4) 0.3196(2) 0.3462(2) 0.0239(6) Uani 1 1 d . . . . .
C14B C 0.4590(5) 0.1547(3) 0.5972(2) 0.0392(8) Uani 1 1 d . . . . .
C15B C 0.5079(4) 0.4848(2) 0.2656(2) 0.0274(7) Uani 1 1 d . . . . .
H15C H 0.5331 0.5109 0.3291 0.033 Uiso 1 1 calc R U . . .
H15D H 0.3894 0.5032 0.2476 0.033 Uiso 1 1 calc R U . . .
C16B C 0.6316(4) 0.5367(2) 0.2025(2) 0.0323(7) Uani 1 1 d . . . . .
H16D H 0.6196 0.6111 0.2067 0.049 Uiso 1 1 calc R U . . .
H16E H 0.7494 0.5202 0.2208 0.049 Uiso 1 1 calc R U . . .
H16F H 0.6057 0.5125 0.1392 0.049 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1A C1A 1.407(4) . ?
N1A C13A 1.420(4) . ?
N1A C15A 1.473(4) . ?
S1A C8A 1.750(3) . ?
S1A C6A 1.755(3) . ?
F1A C7A 1.316(4) . ?
F2A C7A 1.342(4) . ?
F3A C7A 1.333(4) . ?
F4A C14A 1.307(4) . ?
F5A C14A 1.334(4) . ?
F6A C14A 1.328(4) . ?
C1A C2A 1.397(4) . ?
C1A C6A 1.405(4) . ?
C2A C3A 1.383(4) . ?
C2A H2AA 0.9500 . ?
C3A C4A 1.380(4) . ?
C3A H3AA 0.9500 . ?
C4A C5A 1.394(4) . ?
C4A C7A 1.503(4) . ?
C5A C6A 1.380(4) . ?
C5A H5AA 0.9500 . ?
C8A C9A 1.390(4) . ?
C8A C13A 1.406(4) . ?
C9A C10A 1.386(4) . ?
C9A H9AA 0.9500 . ?
C10A C11A 1.380(4) . ?
C10A C14A 1.511(4) . ?
C11A C12A 1.397(4) . ?
C11A H11A 0.9500 . ?
C12A C13A 1.391(4) . ?
C12A H12A 0.9500 . ?
C15A C16A 1.531(4) . ?
C15A H15A 0.9900 . ?
C15A H15B 0.9900 . ?
C16A H16A 0.9800 . ?
C16A H16B 0.9800 . ?
C16A H16C 0.9800 . ?
N1B C1B 1.413(4) . ?
N1B C13B 1.422(4) . ?
N1B C15B 1.464(4) . ?
S1B C8B 1.755(3) . ?
S1B C6B 1.758(3) . ?
F1B C7B 1.327(4) . ?
F2B C7B 1.342(4) . ?
F3B C7B 1.355(4) . ?
F4B C14B 1.319(4) . ?
F5B C14B 1.348(4) . ?
F6B C14B 1.343(4) . ?
C1B C2B 1.391(4) . ?
C1B C6B 1.405(4) . ?
C2B C3B 1.398(4) . ?
C2B H2BA 0.9500 . ?
C3B C4B 1.384(4) . ?
C3B H3BA 0.9500 . ?
C4B C5B 1.386(4) . ?
C4B C7B 1.501(4) . ?
C5B C6B 1.378(4) . ?
C5B H5BA 0.9500 . ?
C8B C9B 1.381(4) . ?
C8B C13B 1.407(4) . ?
C9B C10B 1.390(4) . ?
C9B H9BA 0.9500 . ?
C10B C11B 1.388(5) . ?
C10B C14B 1.507(5) . ?
C11B C12B 1.387(4) . ?
C11B H11B 0.9500 . ?
C12B C13B 1.397(4) . ?
C12B H12B 0.9500 . ?
C15B C16B 1.517(4) . ?
C15B H15C 0.9900 . ?
C15B H15D 0.9900 . ?
C16B H16D 0.9800 . ?
C16B H16E 0.9800 . ?
C16B H16F 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1A N1A C13A 120.8(2) . . ?
C1A N1A C15A 118.4(2) . . ?
C13A N1A C15A 118.2(2) . . ?
C8A S1A C6A 99.19(14) . . ?
C2A C1A N1A 121.7(3) . . ?
C2A C1A C6A 117.7(3) . . ?
N1A C1A C6A 120.6(3) . . ?
C3A C2A C1A 121.0(3) . . ?
C3A C2A H2AA 119.5 . . ?
C1A C2A H2AA 119.5 . . ?
C2A C3A C4A 120.8(3) . . ?
C2A C3A H3AA 119.6 . . ?
C4A C3A H3AA 119.6 . . ?
C3A C4A C5A 119.1(3) . . ?
C3A C4A C7A 121.0(3) . . ?
C5A C4A C7A 119.7(3) . . ?
C6A C5A C4A 120.3(3) . . ?
C6A C5A H5AA 119.8 . . ?
C4A C5A H5AA 119.8 . . ?
C5A C6A C1A 121.0(3) . . ?
C5A C6A S1A 118.2(2) . . ?
C1A C6A S1A 120.6(2) . . ?
F1A C7A F3A 107.1(3) . . ?
F1A C7A F2A 107.8(3) . . ?
F3A C7A F2A 105.1(3) . . ?
F1A C7A C4A 112.9(3) . . ?
F3A C7A C4A 112.4(3) . . ?
F2A C7A C4A 111.1(3) . . ?
C9A C8A C13A 120.9(3) . . ?
C9A C8A S1A 118.1(2) . . ?
C13A C8A S1A 120.7(2) . . ?
C10A C9A C8A 120.4(3) . . ?
C10A C9A H9AA 119.8 . . ?
C8A C9A H9AA 119.8 . . ?
C11A C10A C9A 119.3(3) . . ?
C11A C10A C14A 121.5(3) . . ?
C9A C10A C14A 119.1(3) . . ?
C10A C11A C12A 120.6(3) . . ?
C10A C11A H11A 119.7 . . ?
C12A C11A H11A 119.7 . . ?
C13A C12A C11A 120.9(3) . . ?
C13A C12A H12A 119.6 . . ?
C11A C12A H12A 119.6 . . ?
C12A C13A C8A 117.8(3) . . ?
C12A C13A N1A 121.7(3) . . ?
C8A C13A N1A 120.5(3) . . ?
F4A C14A F6A 107.1(3) . . ?
F4A C14A F5A 106.9(3) . . ?
F6A C14A F5A 106.1(3) . . ?
F4A C14A C10A 113.2(3) . . ?
F6A C14A C10A 111.8(3) . . ?
F5A C14A C10A 111.4(3) . . ?
N1A C15A C16A 115.4(3) . . ?
N1A C15A H15A 108.4 . . ?
C16A C15A H15A 108.4 . . ?
N1A C15A H15B 108.4 . . ?
C16A C15A H15B 108.4 . . ?
H15A C15A H15B 107.5 . . ?
C15A C16A H16A 109.5 . . ?
C15A C16A H16B 109.5 . . ?
H16A C16A H16B 109.5 . . ?
C15A C16A H16C 109.5 . . ?
H16A C16A H16C 109.5 . . ?
H16B C16A H16C 109.5 . . ?
C1B N1B C13B 117.5(2) . . ?
C1B N1B C15B 118.9(2) . . ?
C13B N1B C15B 118.8(2) . . ?
C8B S1B C6B 98.72(14) . . ?
C2B C1B C6B 118.1(3) . . ?
C2B C1B N1B 122.0(3) . . ?
C6B C1B N1B 119.9(3) . . ?
C1B C2B C3B 121.3(3) . . ?
C1B C2B H2BA 119.4 . . ?
C3B C2B H2BA 119.4 . . ?
C4B C3B C2B 119.4(3) . . ?
C4B C3B H3BA 120.3 . . ?
C2B C3B H3BA 120.3 . . ?
C3B C4B C5B 119.9(3) . . ?
C3B C4B C7B 120.9(3) . . ?
C5B C4B C7B 119.1(3) . . ?
C6B C5B C4B 120.7(3) . . ?
C6B C5B H5BA 119.7 . . ?
C4B C5B H5BA 119.7 . . ?
C5B C6B C1B 120.5(3) . . ?
C5B C6B S1B 119.3(2) . . ?
C1B C6B S1B 120.2(2) . . ?
F1B C7B F2B 108.2(3) . . ?
F1B C7B F3B 106.2(3) . . ?
F2B C7B F3B 104.9(3) . . ?
F1B C7B C4B 113.4(3) . . ?
F2B C7B C4B 112.4(3) . . ?
F3B C7B C4B 111.3(3) . . ?
C9B C8B C13B 120.7(3) . . ?
C9B C8B S1B 119.1(2) . . ?
C13B C8B S1B 120.1(2) . . ?
C8B C9B C10B 120.5(3) . . ?
C8B C9B H9BA 119.7 . . ?
C10B C9B H9BA 119.7 . . ?
C11B C10B C9B 119.3(3) . . ?
C11B C10B C14B 121.4(3) . . ?
C9B C10B C14B 119.2(3) . . ?
C12B C11B C10B 120.4(3) . . ?
C12B C11B H11B 119.8 . . ?
C10B C11B H11B 119.8 . . ?
C11B C12B C13B 120.9(3) . . ?
C11B C12B H12B 119.6 . . ?
C13B C12B H12B 119.6 . . ?
C12B C13B C8B 118.1(3) . . ?
C12B C13B N1B 122.1(3) . . ?
C8B C13B N1B 119.8(3) . . ?
F4B C14B F6B 107.8(3) . . ?
F4B C14B F5B 107.4(3) . . ?
F6B C14B F5B 104.9(3) . . ?
F4B C14B C10B 112.5(3) . . ?
F6B C14B C10B 111.9(3) . . ?
F5B C14B C10B 111.9(3) . . ?
N1B C15B C16B 113.1(3) . . ?
N1B C15B H15C 109.0 . . ?
C16B C15B H15C 109.0 . . ?
N1B C15B H15D 109.0 . . ?
C16B C15B H15D 109.0 . . ?
H15C C15B H15D 107.8 . . ?
C15B C16B H16D 109.5 . . ?
C15B C16B H16E 109.5 . . ?
H16D C16B H16E 109.5 . . ?
C15B C16B H16F 109.5 . . ?
H16D C16B H16F 109.5 . . ?
H16E C16B H16F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C13A N1A C1A C2A 151.2(3) . . . . ?
C15A N1A C1A C2A -10.3(4) . . . . ?
C13A N1A C1A C6A -29.5(4) . . . . ?
C15A N1A C1A C6A 169.0(3) . . . . ?
N1A C1A C2A C3A -179.8(3) . . . . ?
C6A C1A C2A C3A 0.9(5) . . . . ?
C1A C2A C3A C4A 0.9(5) . . . . ?
C2A C3A C4A C5A -0.6(5) . . . . ?
C2A C3A C4A C7A -175.8(3) . . . . ?
C3A C4A C5A C6A -1.6(5) . . . . ?
C7A C4A C5A C6A 173.7(3) . . . . ?
C4A C5A C6A C1A 3.5(5) . . . . ?
C4A C5A C6A S1A -171.0(2) . . . . ?
C2A C1A C6A C5A -3.1(4) . . . . ?
N1A C1A C6A C5A 177.6(3) . . . . ?
C2A C1A C6A S1A 171.3(2) . . . . ?
N1A C1A C6A S1A -8.0(4) . . . . ?
C8A S1A C6A C5A -151.0(2) . . . . ?
C8A S1A C6A C1A 34.5(3) . . . . ?
C3A C4A C7A F1A -31.0(5) . . . . ?
C5A C4A C7A F1A 153.7(3) . . . . ?
C3A C4A C7A F3A -152.3(3) . . . . ?
C5A C4A C7A F3A 32.4(4) . . . . ?
C3A C4A C7A F2A 90.2(4) . . . . ?
C5A C4A C7A F2A -85.0(4) . . . . ?
C6A S1A C8A C9A 151.7(2) . . . . ?
C6A S1A C8A C13A -33.1(3) . . . . ?
C13A C8A C9A C10A -3.0(5) . . . . ?
S1A C8A C9A C10A 172.2(2) . . . . ?
C8A C9A C10A C11A 1.9(5) . . . . ?
C8A C9A C10A C14A -174.6(3) . . . . ?
C9A C10A C11A C12A 0.4(5) . . . . ?
C14A C10A C11A C12A 176.9(3) . . . . ?
C10A C11A C12A C13A -1.8(5) . . . . ?
C11A C12A C13A C8A 0.7(4) . . . . ?
C11A C12A C13A N1A -178.1(3) . . . . ?
C9A C8A C13A C12A 1.7(4) . . . . ?
S1A C8A C13A C12A -173.4(2) . . . . ?
C9A C8A C13A N1A -179.5(3) . . . . ?
S1A C8A C13A N1A 5.5(4) . . . . ?
C1A N1A C13A C12A -150.2(3) . . . . ?
C15A N1A C13A C12A 11.3(4) . . . . ?
C1A N1A C13A C8A 31.0(4) . . . . ?
C15A N1A C13A C8A -167.5(3) . . . . ?
C11A C10A C14A F4A 13.5(5) . . . . ?
C9A C10A C14A F4A -170.0(3) . . . . ?
C11A C10A C14A F6A 134.6(3) . . . . ?
C9A C10A C14A F6A -49.0(4) . . . . ?
C11A C10A C14A F5A -107.0(4) . . . . ?
C9A C10A C14A F5A 69.5(4) . . . . ?
C1A N1A C15A C16A 80.5(3) . . . . ?
C13A N1A C15A C16A -81.5(3) . . . . ?
C13B N1B C1B C2B 139.5(3) . . . . ?
C15B N1B C1B C2B -15.8(4) . . . . ?
C13B N1B C1B C6B -41.2(4) . . . . ?
C15B N1B C1B C6B 163.5(3) . . . . ?
C6B C1B C2B C3B -1.6(5) . . . . ?
N1B C1B C2B C3B 177.7(3) . . . . ?
C1B C2B C3B C4B 1.1(5) . . . . ?
C2B C3B C4B C5B 0.8(5) . . . . ?
C2B C3B C4B C7B 179.5(3) . . . . ?
C3B C4B C5B C6B -2.2(5) . . . . ?
C7B C4B C5B C6B 179.0(3) . . . . ?
C4B C5B C6B C1B 1.7(5) . . . . ?
C4B C5B C6B S1B -176.2(2) . . . . ?
C2B C1B C6B C5B 0.2(4) . . . . ?
N1B C1B C6B C5B -179.2(3) . . . . ?
C2B C1B C6B S1B 178.1(2) . . . . ?
N1B C1B C6B S1B -1.3(4) . . . . ?
C8B S1B C6B C5B -148.1(3) . . . . ?
C8B S1B C6B C1B 34.0(3) . . . . ?
C3B C4B C7B F1B -1.5(4) . . . . ?
C5B C4B C7B F1B 177.3(3) . . . . ?
C3B C4B C7B F2B 121.6(3) . . . . ?
C5B C4B C7B F2B -59.6(4) . . . . ?
C3B C4B C7B F3B -121.1(3) . . . . ?
C5B C4B C7B F3B 57.6(4) . . . . ?
C6B S1B C8B C9B 149.6(3) . . . . ?
C6B S1B C8B C13B -34.0(3) . . . . ?
C13B C8B C9B C10B -2.0(5) . . . . ?
S1B C8B C9B C10B 174.3(3) . . . . ?
C8B C9B C10B C11B 3.3(5) . . . . ?
C8B C9B C10B C14B 179.9(3) . . . . ?
C9B C10B C11B C12B -1.9(5) . . . . ?
C14B C10B C11B C12B -178.5(3) . . . . ?
C10B C11B C12B C13B -0.8(5) . . . . ?
C11B C12B C13B C8B 2.0(5) . . . . ?
C11B C12B C13B N1B -176.4(3) . . . . ?
C9B C8B C13B C12B -0.6(5) . . . . ?
S1B C8B C13B C12B -176.9(2) . . . . ?
C9B C8B C13B N1B 177.8(3) . . . . ?
S1B C8B C13B N1B 1.5(4) . . . . ?
C1B N1B C13B C12B -140.5(3) . . . . ?
C15B N1B C13B C12B 14.8(4) . . . . ?
C1B N1B C13B C8B 41.1(4) . . . . ?
C15B N1B C13B C8B -163.6(3) . . . . ?
C11B C10B C14B F4B -18.2(5) . . . . ?
C9B C10B C14B F4B 165.3(3) . . . . ?
C11B C10B C14B F6B 103.5(4) . . . . ?
C9B C10B C14B F6B -73.1(4) . . . . ?
C11B C10B C14B F5B -139.1(3) . . . . ?
C9B C10B C14B F5B 44.3(4) . . . . ?
C1B N1B C15B C16B -61.3(4) . . . . ?
C13B N1B C15B C16B 143.7(3) . . . . ?

_refine_diff_density_max         0.364
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.081


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_k15121
_database_code_depnum_ccdc_archive 'CCDC 1482196'
# CIF edited on-the-fly by script CIFFIX (S. Parkin, 2000-2014). 
# CIFFIX: http://xray.uky.edu/people/parkin/programs/ciffix 
_audit_update_record             
;
2016-05-26 deposited with the CCDC.	2020-05-29 downloaded from the CCDC.
;

_audit_creation_method           'SHELXL-2014/7 and CIFFIX'

_shelx_SHELXL_version_number     2014/7

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H11 F6 N S, Cl6 Sb'
_chemical_formula_sum            'C16 H11 Cl6 F6 N S Sb'
_chemical_formula_weight         697.77

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.7969(2)
_cell_length_b                   26.2133(6)
_cell_length_c                   10.1713(2)
_cell_angle_alpha                90
_cell_angle_beta                 115.8648(8)
_cell_angle_gamma                90
_cell_volume                     2350.42(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    90.0(2)
_cell_measurement_reflns_used    5518
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      27.48

_exptl_crystal_description       block
_exptl_crystal_colour            'dark green'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.972
_exptl_crystal_F_000             1348
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    1.998
_shelx_estimated_absorpt_T_min   0.635
_shelx_estimated_absorpt_T_max   0.754
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.586
_exptl_absorpt_correction_T_max  0.775
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_special_details   
; 
In addition to absorption, multi-scan techniques also correct other slowly 
varying changes in scale factor over reciprocal space, such as those caused 
by x-ray beam inhomogeneity, goniometer imperfection, crystal decomposition, 
crystal longer than the x-ray beam cross section, absorption by the crystal 
mount etc.  These account, by and large, for much of the difference between 
estimated values of Tmin and Tmax and the _exptl_absorpt_correction_ values. 
;

_exptl_special_details           
; 
The crystal was mounted using polyisobutene oil on the tip of a fine glass 
fibre, which was fastened in a copper mounting pin with electrical solder. 
It was placed directly into the cold gas stream of a liquid-nitrogen based 
cryostat (Hope, 1994; Parkin & Hope, 1998). 
 
Diffraction data were collected with the crystal at 90K, which is standard 
practice in this laboratory for the majority of flash-cooled crystals. 
;

_diffrn_ambient_temperature      90.0(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed-tube'
_diffrn_measurement_device_type  'Nonius KappaCCD diffractometer'
_diffrn_measurement_method       'φ and ω scans at fixed χ = 55°'
_diffrn_detector_area_resol_mean 9.1
_diffrn_reflns_number            38485
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.554
_diffrn_reflns_theta_max         27.502
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000

_reflns_number_total             5397
_reflns_number_gt                4278
_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       'COLLECT (Nonius, 1998)'
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 2006)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 2006)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015b)'
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material  
'SHELX (Sheldrick, 2008) and CIFFIX (Parkin, 2013)'

_refine_special_details          
; 
Refinement progress was checked using Platon (Spek, 2009) and by 
an R-tensor (Parkin, 2000). The final model was further checked 
with the IUCr utility checkCIF. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0404P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5397
_refine_ls_number_parameters     281
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0266
_refine_ls_wR_factor_ref         0.0689
_refine_ls_wR_factor_gt          0.0657
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.8165(2) 0.60467(8) 0.5767(2) 0.0223(4) Uani 1 1 d . . . . .
S1 S 1.01907(7) 0.69909(2) 0.59997(7) 0.02664(14) Uani 1 1 d . . . . .
C1 C 0.7513(3) 0.64429(10) 0.4782(3) 0.0236(5) Uani 1 1 d . . . . .
C2 C 0.5989(3) 0.64122(10) 0.3715(3) 0.0285(6) Uani 1 1 d . . . . .
H2 H 0.5408 0.6117 0.3672 0.034 Uiso 1 1 calc R U . . .
C3 C 0.5342(3) 0.67989(11) 0.2748(3) 0.0314(6) Uani 1 1 d . . . . .
H3 H 0.4322 0.6767 0.2030 0.038 Uiso 1 1 calc R U . . .
C4 C 0.6147(3) 0.7238(1) 0.2795(3) 0.0297(6) Uani 1 1 d . . . . .
C5 C 0.7626(3) 0.72889(10) 0.3819(3) 0.0282(6) Uani 1 1 d . . . . .
H5 H 0.8176 0.7592 0.3858 0.034 Uiso 1 1 calc R U . . .
C6 C 0.8319(3) 0.68913(10) 0.4806(3) 0.0247(5) Uani 1 1 d . . . . .
C7 C 1.0736(3) 0.63956(10) 0.6740(2) 0.0231(5) Uani 1 1 d . . . . .
C8 C 1.2305(3) 0.63297(10) 0.7556(3) 0.0264(6) Uani 1 1 d . . . . .
H8 H 1.2977 0.6602 0.7638 0.032 Uiso 1 1 calc R U . . .
C9 C 1.2875(3) 0.58726(10) 0.8237(3) 0.0262(6) Uani 1 1 d . . . . .
C10 C 1.1877(3) 0.54783(10) 0.8142(3) 0.0262(6) Uani 1 1 d . . . . .
H10 H 1.2271 0.5165 0.8627 0.031 Uiso 1 1 calc R U . . .
C11 C 1.0339(3) 0.55366(9) 0.7360(3) 0.0239(5) Uani 1 1 d . . . . .
H11 H 0.9683 0.5264 0.7319 0.029 Uiso 1 1 calc R U . . .
C12 C 0.9715(3) 0.59975(10) 0.6613(2) 0.0211(5) Uani 1 1 d . . . . .
C13 C 0.7149(3) 0.56289(10) 0.5804(3) 0.0272(6) Uani 1 1 d . . . . .
H13A H 0.6147 0.5774 0.5615 0.033 Uiso 1 1 calc R U . . .
H13B H 0.7585 0.5474 0.6791 0.033 Uiso 1 1 calc R U . . .
C14 C 0.6938(3) 0.5216(1) 0.4675(3) 0.0316(6) Uani 1 1 d . . . . .
H14A H 0.6481 0.5366 0.3694 0.047 Uiso 1 1 calc R U . . .
H14B H 0.6271 0.4948 0.4739 0.047 Uiso 1 1 calc R U . . .
H14C H 0.7926 0.5068 0.4866 0.047 Uiso 1 1 calc R U . . .
C15 C 0.5376(3) 0.76564(13) 0.1658(3) 0.0374(7) Uani 1 1 d . . . . .
F1 F 0.5073(2) 0.74888(8) 0.03405(18) 0.0556(5) Uani 1 1 d . . . . .
F2 F 0.4073(2) 0.77871(7) 0.16698(18) 0.0512(5) Uani 1 1 d . . . . .
F3 F 0.6235(2) 0.80670(8) 0.1910(2) 0.0595(5) Uani 1 1 d . . . . .
C16 C 1.4639(3) 0.57964(10) 0.9086(3) 0.0311(6) Uani 1 1 d . . . . .
F4 F 1.5317(2) 0.61996(9) 0.9032(3) 0.1061(11) Uani 1 1 d . . . . .
F5 F 1.4984(2) 0.56855(11) 1.0422(2) 0.0836(8) Uani 1 1 d . . . . .
F6 F 1.5029(2) 0.54186(10) 0.8525(2) 0.0784(8) Uani 1 1 d . . . . .
Sb1 Sb 0.04466(2) 0.87990(2) -0.32408(2) 0.02202(6) Uani 1 1 d . . . . .
Cl1 Cl -0.01281(7) 0.92379(3) -0.14978(7) 0.02921(14) Uani 1 1 d . . . . .
Cl2 Cl 0.09990(7) 0.83422(3) -0.49664(7) 0.03085(15) Uani 1 1 d . . . . .
Cl3 Cl 0.24797(7) 0.93728(3) -0.28200(7) 0.03193(15) Uani 1 1 d . . . . .
Cl4 Cl -0.15815(8) 0.82379(3) -0.36779(7) 0.03295(15) Uani 1 1 d . . . . .
Cl5 Cl -0.11813(7) 0.93550(2) -0.50749(6) 0.02882(14) Uani 1 1 d . . . . .
Cl6 Cl 0.21128(8) 0.82642(3) -0.13738(8) 0.03862(17) 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
N1 C12 1.386(3) . ?
N1 C1 1.390(3) . ?
N1 C13 1.492(3) . ?
S1 C7 1.714(3) . ?
S1 C6 1.721(3) . ?
C1 C6 1.410(4) . ?
C1 C2 1.415(3) . ?
C2 C3 1.361(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.384(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.374(4) . ?
C4 C15 1.532(4) . ?
C5 C6 1.400(3) . ?
C5 H5 0.9500 . ?
C7 C8 1.403(3) . ?
C7 C12 1.412(4) . ?
C8 C9 1.375(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.396(3) . ?
C9 C16 1.572(4) . ?
C10 C11 1.371(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.416(3) . ?
C11 H11 0.9500 . ?
C13 C14 1.525(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 F1 1.315(3) . ?
C15 F3 1.320(4) . ?
C15 F2 1.327(3) . ?
C16 F4 1.262(3) . ?
C16 F5 1.282(3) . ?
C16 F6 1.282(3) . ?
Sb1 Cl6 2.3520(7) . ?
Sb1 Cl4 2.3532(7) . ?
Sb1 Cl5 2.3563(6) . ?
Sb1 Cl2 2.3740(6) . ?
Sb1 Cl1 2.3780(6) . ?
Sb1 Cl3 2.3810(6) . ?

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
C12 N1 C1 123.5(2) . . ?
C12 N1 C13 118.6(2) . . ?
C1 N1 C13 117.7(2) . . ?
C7 S1 C6 101.77(13) . . ?
N1 C1 C6 122.2(2) . . ?
N1 C1 C2 120.7(2) . . ?
C6 C1 C2 117.1(2) . . ?
C3 C2 C1 121.0(3) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C2 C3 C4 121.0(3) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 120.3(2) . . ?
C5 C4 C15 120.8(3) . . ?
C3 C4 C15 118.9(2) . . ?
C4 C5 C6 119.5(3) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C5 C6 C1 121.0(2) . . ?
C5 C6 S1 115.3(2) . . ?
C1 C6 S1 123.69(19) . . ?
C8 C7 C12 120.9(2) . . ?
C8 C7 S1 115.0(2) . . ?
C12 C7 S1 124.1(2) . . ?
C9 C8 C7 120.3(2) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C10 119.5(2) . . ?
C8 C9 C16 119.7(2) . . ?
C10 C9 C16 120.8(2) . . ?
C11 C10 C9 121.1(2) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C10 C11 C12 121.0(2) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
N1 C12 C7 121.9(2) . . ?
N1 C12 C11 120.8(2) . . ?
C7 C12 C11 117.3(2) . . ?
N1 C13 C14 112.0(2) . . ?
N1 C13 H13A 109.2 . . ?
C14 C13 H13A 109.2 . . ?
N1 C13 H13B 109.2 . . ?
C14 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
F1 C15 F3 108.2(2) . . ?
F1 C15 F2 107.7(2) . . ?
F3 C15 F2 108.8(2) . . ?
F1 C15 C4 110.4(2) . . ?
F3 C15 C4 112.0(2) . . ?
F2 C15 C4 109.7(2) . . ?
F4 C16 F5 109.6(3) . . ?
F4 C16 F6 111.3(3) . . ?
F5 C16 F6 107.7(3) . . ?
F4 C16 C9 110.1(2) . . ?
F5 C16 C9 109.2(2) . . ?
F6 C16 C9 108.9(2) . . ?
Cl6 Sb1 Cl4 90.65(3) . . ?
Cl6 Sb1 Cl5 178.37(3) . . ?
Cl4 Sb1 Cl5 90.74(2) . . ?
Cl6 Sb1 Cl2 89.68(2) . . ?
Cl4 Sb1 Cl2 89.49(2) . . ?
Cl5 Sb1 Cl2 91.18(2) . . ?
Cl6 Sb1 Cl1 89.60(2) . . ?
Cl4 Sb1 Cl1 89.33(2) . . ?
Cl5 Sb1 Cl1 89.56(2) . . ?
Cl2 Sb1 Cl1 178.61(2) . . ?
Cl6 Sb1 Cl3 90.00(3) . . ?
Cl4 Sb1 Cl3 179.35(3) . . ?
Cl5 Sb1 Cl3 88.61(2) . . ?
Cl2 Sb1 Cl3 90.51(2) . . ?
Cl1 Sb1 Cl3 90.68(2) . . ?

_refine_diff_density_max         0.806
_refine_diff_density_min         -0.587
_refine_diff_density_rms         0.087


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
