# 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_m17032
_database_code_depnum_ccdc_archive 'CCDC 1589385'
loop_
_audit_author_name
_audit_author_address
'Sean Parkin' UKy
# CIF edited on-the-fly by script CIFFIX (S. Parkin, 2000-2016). 
# CIFFIX: http://xray.uky.edu/people/parkin/programs/ciffix 
_audit_update_record             
;
2017-12-05 deposited with the CCDC.	2020-10-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6

_shelx_SHELXL_version_number     2016/6

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H15 F6 N S'
_chemical_formula_sum            'C18 H15 F6 N S'
_chemical_formula_weight         391.37

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   8.5498(2)
_cell_length_b                   12.3492(4)
_cell_length_c                   16.6921(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1762.41(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    9965
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      27.46

_exptl_crystal_description       'irregular block'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_F_000             800
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.244
_shelx_estimated_absorpt_T_min   0.941
_shelx_estimated_absorpt_T_max   0.962
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.864
_exptl_absorpt_correction_T_max  0.967
_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). 
 
The crystals underwent a destructive phase transition when cooled to 90K. 
Visual inspection of crystal integrity and diffraction quality vs temperature 
established a safe temperature for data collection of -93° C. 
;

_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microsource
_diffrn_measurement_device_type  'Bruker D8 Venture dual source'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 5.6
_diffrn_reflns_number            36398
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_av_R_equivalents  0.0724
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.677
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998

_reflns_number_total             4024
_reflns_number_gt                3329
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.748
_reflns_Friedel_fraction_max     0.995
_reflns_Friedel_fraction_full    0.999
_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       'APEX3 (Bruker-AXS, 2016)'
_computing_cell_refinement       'APEX3 (Bruker-AXS, 2016)'
_computing_data_reduction        'APEX3 (Bruker-AXS, 2016)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2016/6 (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)+(0.0581P)²+0.3252P] 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_abs_structure_details 
; 
Flack 'x' determined using 1215 quotients [(I+)-(I-)]/[(I+)+(I-)] 
[Parsons, Flack and Wagner (2013)]. 
;
_refine_ls_abs_structure_Flack   0.015(18)
_chemical_absolute_configuration .
# Achiral molecule, so 'absolute configuration' is not a relevant concept here. 
_refine_ls_number_reflns         4024
_refine_ls_number_parameters     251
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0430
_refine_ls_wR_factor_ref         0.1096
_refine_ls_wR_factor_gt          0.1049
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.068
_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
S1 S 0.41934(9) 0.33964(6) 0.74804(4) 0.0412(2) Uani 1 1 d . . . . .
N1 N 0.5303(3) 0.19039(19) 0.61680(14) 0.0319(5) Uani 1 1 d . . . . .
F1 F 0.1447(3) -0.0494(2) 0.88225(13) 0.0682(7) Uani 1 1 d . . . . .
F2 F -0.0129(3) 0.0821(2) 0.86529(18) 0.0881(9) Uani 1 1 d . . . . .
F3 F -0.0270(3) -0.0556(2) 0.79023(16) 0.0876(9) Uani 1 1 d . . . . .
C1 C 0.4151(3) 0.1457(2) 0.66827(15) 0.0302(6) Uani 1 1 d . . . . .
C2 C 0.3591(3) 0.0411(2) 0.65429(17) 0.0344(6) Uani 1 1 d . . . . .
C3 C 0.2478(3) -0.0010(3) 0.70665(18) 0.0390(7) Uani 1 1 d . . . . .
H3 H 0.211841 -0.073067 0.699187 0.047 Uiso 1 1 calc R U . . .
C4 C 0.1878(3) 0.0603(3) 0.76973(17) 0.0400(7) Uani 1 1 d . . . . .
C5 C 0.2372(3) 0.1647(3) 0.78116(17) 0.0379(7) Uani 1 1 d . . . . .
H5 H 0.193990 0.207782 0.822811 0.045 Uiso 1 1 calc R U . . .
C6 C 0.3512(3) 0.2065(2) 0.73096(15) 0.0318(6) Uani 1 1 d . . . . .
C7 C 0.4589(3) 0.3773(2) 0.64826(17) 0.0332(6) Uani 1 1 d . . . . .
C8 C 0.4365(4) 0.4841(3) 0.6254(2) 0.0413(7) Uani 1 1 d . . . . .
H8 H 0.395950 0.535449 0.662327 0.050 Uiso 1 1 calc R U . . .
C9 C 0.4739(4) 0.5147(3) 0.5484(2) 0.0423(7) Uani 1 1 d . . . . .
C10 C 0.5296(3) 0.4393(3) 0.49368(19) 0.0385(7) Uani 1 1 d . . . . .
H10 H 0.554584 0.461807 0.440787 0.046 Uiso 1 1 calc R U . . .
C11 C 0.5495(3) 0.3316(2) 0.51492(17) 0.0320(6) Uani 1 1 d . . . . .
C12 C 0.5149(3) 0.3001(2) 0.59418(16) 0.0286(6) Uani 1 1 d . . . . .
C13 C 0.0735(4) 0.0096(3) 0.8259(2) 0.0523(9) Uani 1 1 d . . . . .
C14 C 0.4497(16) 0.6312(8) 0.5228(8) 0.0609(11) Uani 0.715(5) 1 d D . P A 1
F4 F 0.3714(11) 0.6904(4) 0.5736(4) 0.1079(19) Uani 0.715(5) 1 d D . P A 1
F5 F 0.3739(16) 0.6393(4) 0.4567(5) 0.146(3) Uani 0.715(5) 1 d D . P A 1
F6 F 0.5798(6) 0.6819(4) 0.5150(9) 0.152(4) Uani 0.715(5) 1 d D . P A 1
C14' C 0.451(4) 0.6257(17) 0.5205(17) 0.0609(11) Uani 0.285(5) 1 d D . P A 2
F4' F 0.516(3) 0.6500(11) 0.4519(11) 0.1079(19) Uani 0.285(5) 1 d D . P A 2
F5' F 0.507(4) 0.6986(12) 0.5674(12) 0.146(3) Uani 0.285(5) 1 d D . P A 2
F6' F 0.3063(16) 0.6470(13) 0.508(2) 0.152(4) Uani 0.285(5) 1 d D . P A 2
C15 C 0.6012(4) 0.2504(3) 0.45325(18) 0.0417(7) Uani 1 1 d . . . . .
H15A H 0.579991 0.278853 0.399524 0.063 Uiso 1 1 calc R U . . .
H15B H 0.543695 0.182547 0.460922 0.063 Uiso 1 1 calc R U . . .
H15C H 0.713566 0.236915 0.459090 0.063 Uiso 1 1 calc R U . . .
C16 C 0.4121(4) -0.0240(2) 0.58310(18) 0.0421(7) Uani 1 1 d . . . . .
H16A H 0.335299 -0.080911 0.571801 0.063 Uiso 1 1 calc R U . . .
H16B H 0.513758 -0.057150 0.594766 0.063 Uiso 1 1 calc R U . . .
H16C H 0.421823 0.023549 0.536372 0.063 Uiso 1 1 calc R U . . .
C17 C 0.6904(3) 0.1464(3) 0.6251(2) 0.0496(8) Uani 1 1 d . . . . .
H17A H 0.752720 0.168693 0.577874 0.060 Uiso 1 1 calc R U . . .
H17B H 0.684754 0.066313 0.625002 0.060 Uiso 1 1 calc R U . . .
C18 C 0.7731(4) 0.1826(5) 0.6993(3) 0.0862(17) Uani 1 1 d . . . . .
H18A H 0.873480 0.144759 0.703692 0.129 Uiso 1 1 calc R U . . .
H18B H 0.708527 0.165787 0.746249 0.129 Uiso 1 1 calc R U . . .
H18C H 0.791322 0.260820 0.696750 0.129 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
S1 C7 1.762(3) . ?
S1 C6 1.768(3) . ?
N1 C12 1.412(4) . ?
N1 C1 1.419(4) . ?
N1 C17 1.479(4) . ?
F1 C13 1.336(4) . ?
F2 C13 1.333(4) . ?
F3 C13 1.320(4) . ?
C1 C2 1.397(4) . ?
C1 C6 1.398(4) . ?
C2 C3 1.393(4) . ?
C2 C16 1.505(4) . ?
C3 C4 1.394(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.371(5) . ?
C4 C13 1.492(4) . ?
C5 C6 1.385(4) . ?
C5 H5 0.9500 . ?
C7 C8 1.386(4) . ?
C7 C12 1.398(4) . ?
C8 C9 1.377(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.389(5) . ?
C9 C14' 1.46(2) . ?
C9 C14 1.514(9) . ?
C10 C11 1.387(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.410(4) . ?
C11 C15 1.503(4) . ?
C14 F5 1.283(14) . ?
C14 F6 1.283(13) . ?
C14 F4 1.306(14) . ?
C14' F6' 1.28(2) . ?
C14' F5' 1.28(2) . ?
C14' F4' 1.31(2) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.496(6) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 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
C7 S1 C6 98.98(13) . . ?
C12 N1 C1 118.0(2) . . ?
C12 N1 C17 117.6(2) . . ?
C1 N1 C17 116.3(2) . . ?
C2 C1 C6 119.1(3) . . ?
C2 C1 N1 119.7(2) . . ?
C6 C1 N1 121.0(3) . . ?
C3 C2 C1 118.3(3) . . ?
C3 C2 C16 120.1(3) . . ?
C1 C2 C16 121.5(3) . . ?
C2 C3 C4 121.5(3) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C5 C4 C3 120.2(3) . . ?
C5 C4 C13 120.6(3) . . ?
C3 C4 C13 119.2(3) . . ?
C4 C5 C6 118.9(3) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C5 C6 C1 121.9(3) . . ?
C5 C6 S1 118.7(2) . . ?
C1 C6 S1 119.4(2) . . ?
C8 C7 C12 121.2(3) . . ?
C8 C7 S1 119.0(2) . . ?
C12 C7 S1 119.8(2) . . ?
C9 C8 C7 119.1(3) . . ?
C9 C8 H8 120.5 . . ?
C7 C8 H8 120.5 . . ?
C8 C9 C10 120.6(3) . . ?
C8 C9 C14' 121.6(12) . . ?
C10 C9 C14' 117.7(12) . . ?
C8 C9 C14 119.5(6) . . ?
C10 C9 C14 119.9(6) . . ?
C11 C10 C9 121.2(3) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C10 C11 C12 118.6(3) . . ?
C10 C11 C15 120.0(3) . . ?
C12 C11 C15 121.3(3) . . ?
C7 C12 C11 119.3(3) . . ?
C7 C12 N1 120.9(3) . . ?
C11 C12 N1 119.7(2) . . ?
F3 C13 F2 105.7(3) . . ?
F3 C13 F1 106.3(3) . . ?
F2 C13 F1 105.8(3) . . ?
F3 C13 C4 113.5(3) . . ?
F2 C13 C4 113.1(3) . . ?
F1 C13 C4 111.9(3) . . ?
F5 C14 F6 108.3(10) . . ?
F5 C14 F4 104.8(10) . . ?
F6 C14 F4 103.7(9) . . ?
F5 C14 C9 112.7(9) . . ?
F6 C14 C9 111.9(9) . . ?
F4 C14 C9 114.8(9) . . ?
F6' C14' F5' 108(2) . . ?
F6' C14' F4' 102.8(18) . . ?
F5' C14' F4' 102.6(18) . . ?
F6' C14' C9 112(2) . . ?
F5' C14' C9 115(2) . . ?
F4' C14' C9 116(2) . . ?
C11 C15 H15A 109.5 . . ?
C11 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C11 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C2 C16 H16A 109.5 . . ?
C2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C2 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N1 C17 C18 113.9(3) . . ?
N1 C17 H17A 108.8 . . ?
C18 C17 H17A 108.8 . . ?
N1 C17 H17B 108.8 . . ?
C18 C17 H17B 108.8 . . ?
H17A C17 H17B 107.7 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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
C12 N1 C1 C2 138.8(3) . . . . ?
C17 N1 C1 C2 -73.0(3) . . . . ?
C12 N1 C1 C6 -38.3(3) . . . . ?
C17 N1 C1 C6 109.8(3) . . . . ?
C6 C1 C2 C3 -3.7(4) . . . . ?
N1 C1 C2 C3 179.0(2) . . . . ?
C6 C1 C2 C16 174.1(3) . . . . ?
N1 C1 C2 C16 -3.1(4) . . . . ?
C1 C2 C3 C4 2.6(4) . . . . ?
C16 C2 C3 C4 -175.3(3) . . . . ?
C2 C3 C4 C5 0.5(4) . . . . ?
C2 C3 C4 C13 -177.6(3) . . . . ?
C3 C4 C5 C6 -2.4(4) . . . . ?
C13 C4 C5 C6 175.7(3) . . . . ?
C4 C5 C6 C1 1.1(4) . . . . ?
C4 C5 C6 S1 -177.9(2) . . . . ?
C2 C1 C6 C5 2.0(4) . . . . ?
N1 C1 C6 C5 179.1(2) . . . . ?
C2 C1 C6 S1 -179.02(19) . . . . ?
N1 C1 C6 S1 -1.8(3) . . . . ?
C7 S1 C6 C5 -147.4(2) . . . . ?
C7 S1 C6 C1 33.5(2) . . . . ?
C6 S1 C7 C8 146.4(2) . . . . ?
C6 S1 C7 C12 -34.9(2) . . . . ?
C12 C7 C8 C9 -1.5(4) . . . . ?
S1 C7 C8 C9 177.2(2) . . . . ?
C7 C8 C9 C10 1.6(5) . . . . ?
C7 C8 C9 C14' 179.3(14) . . . . ?
C7 C8 C9 C14 179.9(7) . . . . ?
C8 C9 C10 C11 -0.1(5) . . . . ?
C14' C9 C10 C11 -178.0(14) . . . . ?
C14 C9 C10 C11 -178.5(7) . . . . ?
C9 C10 C11 C12 -1.3(4) . . . . ?
C9 C10 C11 C15 176.5(3) . . . . ?
C8 C7 C12 C11 0.1(4) . . . . ?
S1 C7 C12 C11 -178.60(19) . . . . ?
C8 C7 C12 N1 -176.9(3) . . . . ?
S1 C7 C12 N1 4.4(3) . . . . ?
C10 C11 C12 C7 1.3(4) . . . . ?
C15 C11 C12 C7 -176.4(3) . . . . ?
C10 C11 C12 N1 178.4(2) . . . . ?
C15 C11 C12 N1 0.6(4) . . . . ?
C1 N1 C12 C7 36.9(3) . . . . ?
C17 N1 C12 C7 -110.8(3) . . . . ?
C1 N1 C12 C11 -140.1(2) . . . . ?
C17 N1 C12 C11 72.2(3) . . . . ?
C5 C4 C13 F3 143.5(3) . . . . ?
C3 C4 C13 F3 -38.4(4) . . . . ?
C5 C4 C13 F2 23.1(4) . . . . ?
C3 C4 C13 F2 -158.8(3) . . . . ?
C5 C4 C13 F1 -96.2(4) . . . . ?
C3 C4 C13 F1 81.9(4) . . . . ?
C8 C9 C14 F5 -130.(1) . . . . ?
C10 C9 C14 F5 48.3(13) . . . . ?
C8 C9 C14 F6 107.7(12) . . . . ?
C10 C9 C14 F6 -73.9(13) . . . . ?
C8 C9 C14 F4 -10.1(15) . . . . ?
C10 C9 C14 F4 168.3(9) . . . . ?
C8 C9 C14' F6' -74(3) . . . . ?
C10 C9 C14' F6' 104(2) . . . . ?
C8 C9 C14' F5' 49(3) . . . . ?
C10 C9 C14' F5' -133(2) . . . . ?
C8 C9 C14' F4' 168(2) . . . . ?
C10 C9 C14' F4' -14(3) . . . . ?
C12 N1 C17 C18 75.1(4) . . . . ?
C1 N1 C17 C18 -73.2(4) . . . . ?

_refine_diff_density_max         0.291
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.043

####################################################################### 
# 
# 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_m19048
_database_code_depnum_ccdc_archive 'CCDC 2006456'
loop_
_audit_author_name
_audit_author_address
'Sean Parkin'
;UKy
United States of America
;
# CIF edited on-the-fly by script CIFFIX (S. Parkin, 2000-2017). 
# CIFFIX: http://xray.uky.edu/people/parkin/programs/ciffix 
_audit_update_record             
;
2020-05-28 deposited with the CCDC.	2020-10-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3

_shelx_SHELXL_version_number     2018/3

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H17 N S, Cl6 Sb'
_chemical_formula_sum            'C16 H17 Cl6 N S Sb'
_chemical_formula_weight         589.82

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'
Cl Cl 0.1484 0.1585 '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'
Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

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

_cell_length_a                   16.2737(4)
_cell_length_b                   14.3408(3)
_cell_length_c                   9.2087(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2149.11(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    90.0(2)
_cell_measurement_reflns_used    9101
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      27.47

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.823
_exptl_crystal_F_000             1156
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    2.128
_shelx_estimated_absorpt_T_min   0.676
_shelx_estimated_absorpt_T_max   0.727
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.663
_exptl_absorpt_correction_T_max  0.746
_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                   microsource
_diffrn_measurement_device_type  'Bruker D8 Venture dual source'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 7.41
_diffrn_reflns_number            40524
_diffrn_reflns_av_unetI/netI     0.0096
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.541
_diffrn_reflns_theta_max         27.488
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998

_reflns_number_total             2558
_reflns_number_gt                2499
_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       'APEX3 (Bruker-AXS, 2016)'
_computing_cell_refinement       'APEX3 (Bruker-AXS, 2016)'
_computing_data_reduction        'APEX3 (Bruker-AXS, 2016)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2018/3 (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)+(0.0113P)²+1.1185P] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.00124(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2558
_refine_ls_number_parameters     133
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0136
_refine_ls_R_factor_gt           0.0129
_refine_ls_wR_factor_ref         0.0322
_refine_ls_wR_factor_gt          0.0319
_refine_ls_goodness_of_fit_ref   1.189
_refine_ls_restrained_S_all      1.189
_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
Sb1 Sb 0.21826(2) 0.250000 0.21513(2) 0.01149(4) Uani 1 2 d S T P . .
Cl1 Cl 0.08776(3) 0.250000 0.32899(5) 0.01836(9) Uani 1 2 d S T P . .
Cl2 Cl 0.34988(3) 0.250000 0.10211(5) 0.01723(9) Uani 1 2 d S T P . .
Cl3 Cl 0.17532(2) 0.36814(2) 0.05298(3) 0.02208(7) Uani 1 1 d . . . . .
Cl4 Cl 0.26352(2) 0.36692(2) 0.37871(3) 0.01799(7) Uani 1 1 d . . . . .
N1 N 0.46947(9) 0.250000 0.72963(15) 0.0131(3) Uani 1 2 d S T P . .
C7 C 0.41901(13) 0.2454(15) 0.5928(2) 0.0168(11) Uani 0.5 1 d . . P A -1
H7A H 0.362970 0.269152 0.612339 0.020 Uiso 0.5 1 calc R U P A -1
H7B H 0.414338 0.179758 0.560480 0.020 Uiso 0.5 1 calc R U P A -1
C8 C 0.45852(16) 0.3028(2) 0.4750(3) 0.0260(6) Uani 0.5 1 d . . P A -1
H8A H 0.453924 0.369136 0.499285 0.039 Uiso 0.5 1 calc R U P A -1
H8B H 0.430695 0.290847 0.382446 0.039 Uiso 0.5 1 calc R U P A -1
H8C H 0.516653 0.285815 0.466497 0.039 Uiso 0.5 1 calc R U P A -1
S1 S 0.65354(3) 0.250000 0.79734(5) 0.01574(9) Uani 1 2 d S T P . .
C1 C 0.50252(7) 0.33510(8) 0.77347(12) 0.0133(2) Uani 1 1 d . . . . .
C2 C 0.45170(8) 0.41516(9) 0.78349(13) 0.0173(2) Uani 1 1 d . . . . .
C3 C 0.48891(9) 0.50007(9) 0.80978(15) 0.0224(3) Uani 1 1 d . . . . .
H3 H 0.455630 0.554354 0.815839 0.027 Uiso 1 1 calc R U . . .
C4 C 0.57413(9) 0.50888(9) 0.82784(16) 0.0241(3) Uani 1 1 d . . . . .
H4 H 0.597897 0.568810 0.840863 0.029 Uiso 1 1 calc R U . . .
C5 C 0.62307(8) 0.43139(9) 0.82673(14) 0.0199(3) Uani 1 1 d . . . . .
H5 H 0.680544 0.436999 0.842514 0.024 Uiso 1 1 calc R U . . .
C6 C 0.58780(7) 0.34356(9) 0.80212(12) 0.0142(2) Uani 1 1 d . . . . .
C9 C 0.35930(8) 0.41019(9) 0.77568(15) 0.0223(3) Uani 1 1 d . . . . .
H9A H 0.341703 0.415586 0.674256 0.033 Uiso 1 1 calc R U . . .
H9B H 0.335514 0.461328 0.832392 0.033 Uiso 1 1 calc R U . . .
H9C H 0.340609 0.350425 0.815324 0.033 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
Sb1 Cl3 2.3640(3) . ?
Sb1 Cl3 2.3640(3) 7_565 ?
Sb1 Cl1 2.3684(4) . ?
Sb1 Cl4 2.3712(3) . ?
Sb1 Cl4 2.3713(3) 7_565 ?
Sb1 Cl2 2.3814(4) . ?
N1 C1 1.3934(13) 7_565 ?
N1 C1 1.3935(14) . ?
N1 C7 1.505(3) . ?
C7 C8 1.507(12) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
S1 C6 1.7166(13) 7_565 ?
S1 C6 1.7166(13) . ?
C1 C6 1.4178(17) . ?
C1 C2 1.4180(17) . ?
C2 C3 1.3812(19) . ?
C2 C9 1.5071(18) . ?
C3 C4 1.403(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.3672(19) . ?
C4 H4 0.9500 . ?
C5 C6 1.4026(17) . ?
C5 H5 0.9500 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 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
Cl3 Sb1 Cl3 91.561(16) . 7_565 ?
Cl3 Sb1 Cl1 90.833(11) . . ?
Cl3 Sb1 Cl1 90.832(11) 7_565 . ?
Cl3 Sb1 Cl4 89.216(11) . . ?
Cl3 Sb1 Cl4 178.963(12) 7_565 . ?
Cl1 Sb1 Cl4 89.843(11) . . ?
Cl3 Sb1 Cl4 178.961(12) . 7_565 ?
Cl3 Sb1 Cl4 89.216(11) 7_565 7_565 ?
Cl1 Sb1 Cl4 89.844(11) . 7_565 ?
Cl4 Sb1 Cl4 89.998(15) . 7_565 ?
Cl3 Sb1 Cl2 89.418(11) . . ?
Cl3 Sb1 Cl2 89.419(11) 7_565 . ?
Cl1 Sb1 Cl2 179.640(15) . . ?
Cl4 Sb1 Cl2 89.902(11) . . ?
Cl4 Sb1 Cl2 89.901(11) 7_565 . ?
C1 N1 C1 122.28(14) 7_565 . ?
C1 N1 C7 114.5(8) 7_565 . ?
C1 N1 C7 119.4(8) . . ?
N1 C7 C8 110.2(7) . . ?
N1 C7 H7A 109.6 . . ?
C8 C7 H7A 109.6 . . ?
N1 C7 H7B 109.6 . . ?
C8 C7 H7B 109.6 . . ?
H7A C7 H7B 108.1 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 S1 C6 102.82(8) 7_565 . ?
N1 C1 C6 120.44(11) . . ?
N1 C1 C2 120.19(11) . . ?
C6 C1 C2 119.31(11) . . ?
C3 C2 C1 118.00(12) . . ?
C3 C2 C9 119.17(12) . . ?
C1 C2 C9 122.72(12) . . ?
C2 C3 C4 122.26(13) . . ?
C2 C3 H3 118.9 . . ?
C4 C3 H3 118.9 . . ?
C5 C4 C3 120.12(12) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 119.52(12) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C5 C6 C1 120.50(11) . . ?
C5 C6 S1 116.81(9) . . ?
C1 C6 S1 122.57(9) . . ?
C2 C9 H9A 109.5 . . ?
C2 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C2 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 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
C1 N1 C7 C8 -116.4(10) 7_565 . . . ?
C1 N1 C7 C8 42.2(10) . . . . ?
C1 N1 C1 C6 30.6(2) 7_565 . . . ?
C7 N1 C1 C6 -126.3(2) . . . . ?
C1 N1 C1 C2 -152.27(10) 7_565 . . . ?
C7 N1 C1 C2 50.8(3) . . . . ?
N1 C1 C2 C3 -172.12(12) . . . . ?
C6 C1 C2 C3 5.05(17) . . . . ?
N1 C1 C2 C9 11.67(19) . . . . ?
C6 C1 C2 C9 -171.16(11) . . . . ?
C1 C2 C3 C4 -0.6(2) . . . . ?
C9 C2 C3 C4 175.76(13) . . . . ?
C2 C3 C4 C5 -3.2(2) . . . . ?
C3 C4 C5 C6 2.3(2) . . . . ?
C4 C5 C6 C1 2.21(19) . . . . ?
C4 C5 C6 S1 178.25(11) . . . . ?
N1 C1 C6 C5 171.21(12) . . . . ?
C2 C1 C6 C5 -5.95(18) . . . . ?
N1 C1 C6 S1 -4.60(17) . . . . ?
C2 C1 C6 S1 178.24(9) . . . . ?
C6 S1 C6 C5 168.48(7) 7_565 . . . ?
C6 S1 C6 C1 -15.57(14) 7_565 . . . ?

_refine_diff_density_max         0.374
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.049

####################################################################### 
# 
# 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_m19039
_database_code_depnum_ccdc_archive 'CCDC 2006457'
loop_
_audit_author_name
_audit_author_address
'Sean Parkin'
;UKy
United States of America
;
# CIF edited on-the-fly by script CIFFIX (S. Parkin, 2000-2017). 
# CIFFIX: http://xray.uky.edu/people/parkin/programs/ciffix 
_audit_update_record             
;
2020-05-28 deposited with the CCDC.	2020-10-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3

_shelx_SHELXL_version_number     2018/3

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C18 H15 F6 N S), 2(Cl6 Sb), C H2 Cl2'
_chemical_formula_sum            'C37 H32 Cl14 F12 N2 S2 Sb2'
_chemical_formula_weight         1536.56

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'
Cl Cl 0.1484 0.1585 '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'
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'
Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'

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

_cell_length_a                   19.1219(5)
_cell_length_b                   20.2953(5)
_cell_length_c                   13.6777(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5308.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    90.0(2)
_cell_measurement_reflns_used    9976
_cell_measurement_theta_min      2.72
_cell_measurement_theta_max      27.39

_exptl_crystal_description       needle
_exptl_crystal_colour            'deep purple'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.923
_exptl_crystal_F_000             2992
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    1.876
_shelx_estimated_absorpt_T_min   0.662
_shelx_estimated_absorpt_T_max   0.963
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.802
_exptl_absorpt_correction_T_max  0.862
_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                   microsource
_diffrn_measurement_device_type  'Bruker D8 Venture dual source'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 7.41
_diffrn_reflns_number            38894
_diffrn_reflns_av_unetI/netI     0.0552
_diffrn_reflns_av_R_equivalents  0.0649
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.717
_diffrn_reflns_theta_max         27.473
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998

_reflns_number_total             6078
_reflns_number_gt                4371
_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       'APEX3 (Bruker-AXS, 2016)'
_computing_cell_refinement       'APEX3 (Bruker-AXS, 2016)'
_computing_data_reduction        'APEX3 (Bruker-AXS, 2016)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2018/3 (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)+(0.0208P)²+1.0898P] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.00023(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6078
_refine_ls_number_parameters     316
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0601
_refine_ls_R_factor_gt           0.0330
_refine_ls_wR_factor_ref         0.0679
_refine_ls_wR_factor_gt          0.0603
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_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
Sb1 Sb 0.59694(2) 0.58378(2) 0.24519(2) 0.01445(7) Uani 1 1 d . . . . .
Cl1 Cl 0.61497(6) 0.48264(4) 0.32874(6) 0.0264(2) Uani 1 1 d . . . . .
Cl2 Cl 0.57808(5) 0.68464(4) 0.16308(6) 0.0233(2) Uani 1 1 d . . . . .
Cl3 Cl 0.49645(5) 0.60477(5) 0.34175(6) 0.0262(2) Uani 1 1 d . . . . .
Cl4 Cl 0.69681(5) 0.56431(5) 0.14845(6) 0.0249(2) Uani 1 1 d . . . . .
Cl5 Cl 0.66803(5) 0.63751(4) 0.36129(6) 0.0222(2) Uani 1 1 d . . . . .
Cl6 Cl 0.52694(5) 0.52853(4) 0.12882(5) 0.0236(2) Uani 1 1 d . . . . .
S1 S 0.41945(5) 0.42735(4) 0.42559(5) 0.0185(2) Uani 1 1 d . . . . .
F1 F 0.61075(14) 0.19826(10) 0.34714(16) 0.0389(6) Uani 1 1 d . . . . .
F2 F 0.68169(13) 0.27983(12) 0.34423(15) 0.0366(6) Uani 1 1 d . . . . .
F3 F 0.61823(12) 0.26237(10) 0.47162(13) 0.0279(5) Uani 1 1 d . . . . .
F4 F 0.27343(12) 0.63416(10) 0.48419(13) 0.0281(6) Uani 1 1 d . . . . .
F5 F 0.29435(14) 0.69158(10) 0.35569(15) 0.0382(7) Uani 1 1 d . . . . .
F6 F 0.20011(14) 0.63392(12) 0.36539(16) 0.0436(7) Uani 1 1 d . . . . .
N1 N 0.40248(16) 0.41649(13) 0.20242(17) 0.0146(6) Uani 1 1 d . . . . .
C1 C 0.45849(19) 0.38226(16) 0.2428(2) 0.0143(7) Uani 1 1 d . . . . .
C2 C 0.5068(2) 0.34703(16) 0.1840(2) 0.0177(8) Uani 1 1 d . . . . .
C3 C 0.5564(2) 0.30871(16) 0.2286(2) 0.0181(8) Uani 1 1 d . . . . .
H3 H 0.588004 0.284264 0.189061 0.022 Uiso 1 1 calc R U . . .
C4 C 0.5622(2) 0.30435(16) 0.3312(2) 0.0167(8) Uani 1 1 d . . . . .
C5 C 0.5196(2) 0.34154(16) 0.3892(2) 0.0155(8) Uani 1 1 d . . . . .
H5 H 0.524461 0.340192 0.458308 0.019 Uiso 1 1 calc R U . . .
C6 C 0.46886(19) 0.38161(16) 0.3461(2) 0.0137(7) Uani 1 1 d . . . . .
C7 C 0.37575(19) 0.48027(16) 0.3494(2) 0.0136(7) Uani 1 1 d . . . . .
C8 C 0.34123(19) 0.53196(17) 0.3960(2) 0.0157(8) Uani 1 1 d . . . . .
H8 H 0.342431 0.535832 0.465171 0.019 Uiso 1 1 calc R U . . .
C9 C 0.3056(2) 0.57705(16) 0.3408(2) 0.0164(8) Uani 1 1 d . . . . .
C10 C 0.30612(19) 0.57196(16) 0.2382(2) 0.0173(8) Uani 1 1 d . . . . .
H10 H 0.282772 0.604706 0.200803 0.021 Uiso 1 1 calc R U . . .
C11 C 0.3392(2) 0.52137(17) 0.1902(2) 0.0171(8) Uani 1 1 d . . . . .
C12 C 0.37306(19) 0.47195(16) 0.2467(2) 0.0148(7) Uani 1 1 d . . . . .
C13 C 0.3603(2) 0.38355(17) 0.1227(2) 0.0201(8) Uani 1 1 d . . . . .
H13A H 0.385607 0.387398 0.059821 0.024 Uiso 1 1 calc R U . . .
H13B H 0.314856 0.406506 0.115655 0.024 Uiso 1 1 calc R U . . .
C14 C 0.3473(2) 0.31138(17) 0.1448(3) 0.0282(10) Uani 1 1 d . . . . .
H14A H 0.315453 0.292953 0.095749 0.042 Uiso 1 1 calc R U . . .
H14B H 0.326187 0.307152 0.209858 0.042 Uiso 1 1 calc R U . . .
H14C H 0.391710 0.287376 0.143243 0.042 Uiso 1 1 calc R U . . .
C15 C 0.6180(2) 0.26123(18) 0.3734(2) 0.0228(9) Uani 1 1 d . . . . .
C16 C 0.2681(2) 0.63371(18) 0.3864(2) 0.0238(9) Uani 1 1 d . . . . .
C17 C 0.5102(2) 0.35417(18) 0.0736(2) 0.0242(9) Uani 1 1 d . . . . .
H17A H 0.557442 0.343281 0.050885 0.036 Uiso 1 1 calc R U . . .
H17B H 0.499016 0.399657 0.055388 0.036 Uiso 1 1 calc R U . . .
H17C H 0.476429 0.324171 0.043279 0.036 Uiso 1 1 calc R U . . .
C18 C 0.3425(2) 0.52486(18) 0.0794(2) 0.0233(9) Uani 1 1 d . . . . .
H18A H 0.301663 0.502533 0.051572 0.035 Uiso 1 1 calc R U . . .
H18B H 0.385277 0.503225 0.056510 0.035 Uiso 1 1 calc R U . . .
H18C H 0.342692 0.571090 0.058734 0.035 Uiso 1 1 calc R U . . .
Cl1S Cl 0.69629(6) 0.69919(5) 0.57473(7) 0.0372(3) Uani 1 1 d . . . . .
C1S C 0.750000 0.750000 0.6486(3) 0.0297(14) Uani 1 2 d S T P . .
H1SA H 0.720304 0.777870 0.691136 0.036 Uiso 0.5 1 calc R U P . .
H1SB H 0.779696 0.722130 0.691136 0.036 Uiso 0.5 1 calc R U P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Sb1 Cl4 2.3568(10) . ?
Sb1 Cl5 2.3576(9) . ?
Sb1 Cl2 2.3624(9) . ?
Sb1 Cl6 2.3627(9) . ?
Sb1 Cl3 2.3702(10) . ?
Sb1 Cl1 2.3745(9) . ?
S1 C6 1.713(3) . ?
S1 C7 1.714(3) . ?
F1 C15 1.335(4) . ?
F2 C15 1.336(4) . ?
F3 C15 1.343(4) . ?
F4 C16 1.341(4) . ?
F5 C16 1.345(4) . ?
F6 C16 1.332(5) . ?
N1 C1 1.391(4) . ?
N1 C12 1.397(4) . ?
N1 C13 1.513(4) . ?
C1 C2 1.418(5) . ?
C1 C6 1.428(4) . ?
C2 C3 1.370(5) . ?
C2 C17 1.518(4) . ?
C3 C4 1.411(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.364(5) . ?
C4 C15 1.496(5) . ?
C5 C6 1.397(5) . ?
C5 H5 0.9500 . ?
C7 C8 1.393(4) . ?
C7 C12 1.416(4) . ?
C8 C9 1.368(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.408(4) . ?
C9 C16 1.492(5) . ?
C10 C11 1.373(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.423(5) . ?
C11 C18 1.517(4) . ?
C13 C14 1.516(5) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
Cl1S C1S 1.772(3) . ?
C1S H1SA 0.9900 . ?
C1S H1SB 0.9900 . ?

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
Cl4 Sb1 Cl5 89.34(3) . . ?
Cl4 Sb1 Cl2 90.12(3) . . ?
Cl5 Sb1 Cl2 90.43(3) . . ?
Cl4 Sb1 Cl6 90.07(3) . . ?
Cl5 Sb1 Cl6 179.09(4) . . ?
Cl2 Sb1 Cl6 90.25(3) . . ?
Cl4 Sb1 Cl3 179.27(3) . . ?
Cl5 Sb1 Cl3 90.52(3) . . ?
Cl2 Sb1 Cl3 89.17(3) . . ?
Cl6 Sb1 Cl3 90.08(3) . . ?
Cl4 Sb1 Cl1 90.43(3) . . ?
Cl5 Sb1 Cl1 89.54(3) . . ?
Cl2 Sb1 Cl1 179.45(4) . . ?
Cl6 Sb1 Cl1 89.78(3) . . ?
Cl3 Sb1 Cl1 90.28(3) . . ?
C6 S1 C7 102.88(15) . . ?
C1 N1 C12 122.7(3) . . ?
C1 N1 C13 118.4(3) . . ?
C12 N1 C13 117.0(3) . . ?
N1 C1 C2 121.9(3) . . ?
N1 C1 C6 120.3(3) . . ?
C2 C1 C6 117.8(3) . . ?
C3 C2 C1 119.0(3) . . ?
C3 C2 C17 117.8(3) . . ?
C1 C2 C17 122.9(3) . . ?
C2 C3 C4 122.2(3) . . ?
C2 C3 H3 118.9 . . ?
C4 C3 H3 118.9 . . ?
C5 C4 C3 119.8(3) . . ?
C5 C4 C15 121.7(3) . . ?
C3 C4 C15 118.4(3) . . ?
C4 C5 C6 119.4(3) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C5 C6 C1 121.3(3) . . ?
C5 C6 S1 115.5(2) . . ?
C1 C6 S1 123.1(3) . . ?
C8 C7 C12 121.7(3) . . ?
C8 C7 S1 115.2(2) . . ?
C12 C7 S1 123.1(3) . . ?
C9 C8 C7 119.2(3) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C8 C9 C10 119.8(3) . . ?
C8 C9 C16 121.6(3) . . ?
C10 C9 C16 118.5(3) . . ?
C11 C10 C9 122.4(3) . . ?
C11 C10 H10 118.8 . . ?
C9 C10 H10 118.8 . . ?
C10 C11 C12 118.5(3) . . ?
C10 C11 C18 117.5(3) . . ?
C12 C11 C18 123.8(3) . . ?
N1 C12 C7 120.8(3) . . ?
N1 C12 C11 121.0(3) . . ?
C7 C12 C11 118.2(3) . . ?
N1 C13 C14 111.7(3) . . ?
N1 C13 H13A 109.3 . . ?
C14 C13 H13A 109.3 . . ?
N1 C13 H13B 109.3 . . ?
C14 C13 H13B 109.3 . . ?
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 F2 106.5(3) . . ?
F1 C15 F3 106.6(3) . . ?
F2 C15 F3 106.9(3) . . ?
F1 C15 C4 112.5(3) . . ?
F2 C15 C4 111.7(3) . . ?
F3 C15 C4 112.2(3) . . ?
F6 C16 F4 106.8(3) . . ?
F6 C16 F5 107.1(3) . . ?
F4 C16 F5 106.1(3) . . ?
F6 C16 C9 112.4(3) . . ?
F4 C16 C9 112.7(3) . . ?
F5 C16 C9 111.3(3) . . ?
C2 C17 H17A 109.5 . . ?
C2 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C2 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C11 C18 H18A 109.5 . . ?
C11 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C11 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
Cl1S C1S Cl1S 110.4(3) 2_665 . ?
Cl1S C1S H1SA 109.6 2_665 . ?
Cl1S C1S H1SA 109.6 . . ?
Cl1S C1S H1SB 109.6 2_665 . ?
Cl1S C1S H1SB 109.6 . . ?
H1SA C1S H1SB 108.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C12 N1 C1 C2 -151.7(3) . . . . ?
C13 N1 C1 C2 44.2(4) . . . . ?
C12 N1 C1 C6 28.4(5) . . . . ?
C13 N1 C1 C6 -135.8(3) . . . . ?
N1 C1 C2 C3 -173.2(3) . . . . ?
C6 C1 C2 C3 6.7(5) . . . . ?
N1 C1 C2 C17 12.1(5) . . . . ?
C6 C1 C2 C17 -168.0(3) . . . . ?
C1 C2 C3 C4 -1.6(5) . . . . ?
C17 C2 C3 C4 173.4(3) . . . . ?
C2 C3 C4 C5 -3.2(6) . . . . ?
C2 C3 C4 C15 180.0(3) . . . . ?
C3 C4 C5 C6 2.5(5) . . . . ?
C15 C4 C5 C6 179.2(3) . . . . ?
C4 C5 C6 C1 2.8(5) . . . . ?
C4 C5 C6 S1 -178.8(3) . . . . ?
N1 C1 C6 C5 172.4(3) . . . . ?
C2 C1 C6 C5 -7.5(5) . . . . ?
N1 C1 C6 S1 -5.8(5) . . . . ?
C2 C1 C6 S1 174.3(3) . . . . ?
C7 S1 C6 C5 169.2(3) . . . . ?
C7 S1 C6 C1 -12.4(3) . . . . ?
C6 S1 C7 C8 -168.4(3) . . . . ?
C6 S1 C7 C12 13.0(3) . . . . ?
C12 C7 C8 C9 -2.1(5) . . . . ?
S1 C7 C8 C9 179.3(3) . . . . ?
C7 C8 C9 C10 -2.1(5) . . . . ?
C7 C8 C9 C16 -179.5(3) . . . . ?
C8 C9 C10 C11 2.6(6) . . . . ?
C16 C9 C10 C11 -179.8(3) . . . . ?
C9 C10 C11 C12 1.0(5) . . . . ?
C9 C10 C11 C18 -173.9(3) . . . . ?
C1 N1 C12 C7 -27.9(5) . . . . ?
C13 N1 C12 C7 136.5(3) . . . . ?
C1 N1 C12 C11 152.6(3) . . . . ?
C13 N1 C12 C11 -43.1(4) . . . . ?
C8 C7 C12 N1 -174.0(3) . . . . ?
S1 C7 C12 N1 4.6(5) . . . . ?
C8 C7 C12 C11 5.6(5) . . . . ?
S1 C7 C12 C11 -175.9(3) . . . . ?
C10 C11 C12 N1 174.6(3) . . . . ?
C18 C11 C12 N1 -10.8(6) . . . . ?
C10 C11 C12 C7 -5.0(5) . . . . ?
C18 C11 C12 C7 169.6(3) . . . . ?
C1 N1 C13 C14 41.5(4) . . . . ?
C12 N1 C13 C14 -123.6(3) . . . . ?
C5 C4 C15 F1 122.6(4) . . . . ?
C3 C4 C15 F1 -60.7(4) . . . . ?
C5 C4 C15 F2 -117.7(4) . . . . ?
C3 C4 C15 F2 59.1(4) . . . . ?
C5 C4 C15 F3 2.4(5) . . . . ?
C3 C4 C15 F3 179.1(3) . . . . ?
C8 C9 C16 F6 -121.2(4) . . . . ?
C10 C9 C16 F6 61.3(4) . . . . ?
C8 C9 C16 F4 -0.4(5) . . . . ?
C10 C9 C16 F4 -177.9(3) . . . . ?
C8 C9 C16 F5 118.7(4) . . . . ?
C10 C9 C16 F5 -58.8(5) . . . . ?

_refine_diff_density_max         0.542
_refine_diff_density_min         -0.944
_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_m19116
_database_code_depnum_ccdc_archive 'CCDC 2006455'
loop_
_audit_author_name
_audit_author_address
'Sean Parkin'
;UKy
United States of America
;
# CIF edited on-the-fly by script CIFFIX (S. Parkin, 2000-2017). 
# CIFFIX: http://xray.uky.edu/people/parkin/programs/ciffix 
_audit_update_record             
;
2020-05-28 deposited with the CCDC.	2020-10-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3

_shelx_SHELXL_version_number     2018/3

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H17 N S, Cl6 Sb'
_chemical_formula_sum            'C16 H17 Cl6 N S Sb'
_chemical_formula_weight         589.82

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'
Cl Cl 0.1484 0.1585 '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'
Sb Sb -0.5866 1.5461 '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                   9.2759(1)
_cell_length_b                   9.5607(1)
_cell_length_c                   12.5247(2)
_cell_angle_alpha                76.2187(5)
_cell_angle_beta                 87.2025(5)
_cell_angle_gamma                81.9614(5)
_cell_volume                     1068.03(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    90.0(2)
_cell_measurement_reflns_used    9889
_cell_measurement_theta_min      2.76
_cell_measurement_theta_max      27.48

_exptl_crystal_description       slab
_exptl_crystal_colour            'dark green'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.834
_exptl_crystal_F_000             578
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    2.141
_shelx_estimated_absorpt_T_min   0.617
_shelx_estimated_absorpt_T_max   0.847
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.625
_exptl_absorpt_correction_T_max  0.746
_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                   microsource
_diffrn_measurement_device_type  'Bruker D8 Venture dual source'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 7.41
_diffrn_reflns_number            28245
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.758
_diffrn_reflns_theta_max         27.489
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998

_reflns_number_total             4887
_reflns_number_gt                4490
_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       'APEX3 (Bruker-AXS, 2016)'
_computing_cell_refinement       'APEX3 (Bruker-AXS, 2016)'
_computing_data_reduction        'APEX3 (Bruker-AXS, 2016)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2018/3 (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)+(0.0168P)²+1.3284P] 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         4887
_refine_ls_number_parameters     256
_refine_ls_number_restraints     87
_refine_ls_R_factor_all          0.0259
_refine_ls_R_factor_gt           0.0227
_refine_ls_wR_factor_ref         0.0539
_refine_ls_wR_factor_gt          0.0518
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.045
_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
Sb1 Sb 0.500000 0.500000 1.000000 0.02287(6) Uani 1 2 d S . P . .
Cl1 Cl 0.29629(7) 0.39503(7) 1.08653(5) 0.03619(13) Uani 1 1 d . . . . .
Cl2 Cl 0.40389(7) 0.72400(6) 1.04147(5) 0.03731(14) Uani 1 1 d . . . . .
Cl3 Cl 0.37764(7) 0.56994(7) 0.83046(5) 0.03821(14) Uani 1 1 d . . . . .
Sb2 Sb 0.000000 0.000000 0.500000 0.02210(6) Uani 1 2 d S . P . .
Cl4 Cl 0.21417(7) -0.15147(7) 0.57072(7) 0.04912(19) Uani 1 1 d . . . . .
Cl5 Cl -0.01571(7) 0.10525(7) 0.65402(5) 0.03610(14) Uani 1 1 d . . . . .
Cl6 Cl 0.13971(8) 0.17953(8) 0.40537(6) 0.04742(17) Uani 1 1 d . . . . .
S1 S 0.08395(6) 0.44280(6) 0.70631(5) 0.02691(12) Uani 1 1 d . . . . .
N1 N 0.3135(3) 0.1652(3) 0.7324(2) 0.0231(5) Uani 0.846(4) 1 d D U P A 1
C13 C 0.4023(3) 0.0217(3) 0.7362(2) 0.0279(6) Uani 0.846(4) 1 d D U P A 1
H13A H 0.412009 0.005108 0.660927 0.033 Uiso 0.846(4) 1 calc R U P A 1
H13B H 0.350633 -0.055824 0.782258 0.033 Uiso 0.846(4) 1 calc R U P A 1
C14 C 0.5540(3) 0.0108(3) 0.7822(3) 0.0325(7) Uani 0.846(4) 1 d D U P A 1
H14A H 0.606391 -0.086400 0.785129 0.049 Uiso 0.846(4) 1 calc R U P A 1
H14B H 0.545207 0.028105 0.856447 0.049 Uiso 0.846(4) 1 calc R U P A 1
H14C H 0.607761 0.083739 0.734618 0.049 Uiso 0.846(4) 1 calc R U P A 1
N1' N 0.3543(14) 0.1972(14) 0.7421(13) 0.0231(5) Uani 0.154(4) 1 d D U P A 2
C13' C 0.4872(13) 0.0881(13) 0.7641(12) 0.025(2) Uani 0.154(4) 1 d D U P A 2
H13C H 0.509343 0.066117 0.843343 0.030 Uiso 0.154(4) 1 calc R U P A 2
H13D H 0.570652 0.130411 0.722581 0.030 Uiso 0.154(4) 1 calc R U P A 2
C14' C 0.4706(16) -0.0524(13) 0.7320(13) 0.030(3) Uani 0.154(4) 1 d D U P A 2
H14D H 0.563572 -0.116366 0.741212 0.045 Uiso 0.154(4) 1 calc R U P A 2
H14E H 0.441444 -0.030528 0.654953 0.045 Uiso 0.154(4) 1 calc R U P A 2
H14F H 0.395936 -0.100772 0.778996 0.045 Uiso 0.154(4) 1 calc R U P A 2
C1 C 0.2303(2) 0.1842(2) 0.82355(19) 0.0268(5) Uani 1 1 d . . . . .
C2 C 0.2453(3) 0.0778(3) 0.9233(2) 0.0307(5) Uani 1 1 d . . . . .
H2 H 0.317524 -0.004331 0.928583 0.037 Uiso 1 1 calc R U . . .
C3 C 0.1582(3) 0.0905(3) 1.0123(2) 0.0318(5) Uani 1 1 d . . . . .
H3 H 0.170855 0.016160 1.077981 0.038 Uiso 1 1 calc R U . . .
C4 C 0.0505(3) 0.2097(3) 1.01015(19) 0.0307(5) Uani 1 1 d . . . . .
C5 C 0.0334(2) 0.3139(3) 0.91303(19) 0.0280(5) Uani 1 1 d . . . . .
H5 H -0.039884 0.394997 0.908784 0.034 Uiso 1 1 calc R U . . .
C6 C 0.1209(2) 0.3036(2) 0.82060(18) 0.0243(4) Uani 1 1 d . . . . .
C7 C 0.2167(2) 0.4011(2) 0.61408(18) 0.0230(4) Uani 1 1 d . . . . .
C8 C 0.2156(2) 0.5011(2) 0.51186(18) 0.0246(4) Uani 1 1 d . . . . .
H8 H 0.143373 0.583869 0.498314 0.030 Uiso 1 1 calc R U . . .
C9 C 0.3168(2) 0.4821(2) 0.43088(19) 0.0261(4) Uani 1 1 d . . . . .
C10 C 0.4233(2) 0.3595(3) 0.45473(19) 0.0276(5) Uani 1 1 d . . . . .
H10 H 0.496109 0.345921 0.400762 0.033 Uiso 1 1 calc R U . . .
C11 C 0.4256(2) 0.2595(3) 0.55290(19) 0.0284(5) Uani 1 1 d . . . . .
H11 H 0.499543 0.178214 0.565677 0.034 Uiso 1 1 calc R U . . .
C12 C 0.3199(2) 0.2747(2) 0.63566(18) 0.0261(4) Uani 1 1 d . . . . .
C15 C -0.0384(3) 0.2251(3) 1.1110(2) 0.0409(6) Uani 1 1 d . . . . .
H15A H -0.110752 0.311934 1.092879 0.061 Uiso 1 1 calc R U . . .
H15B H 0.025645 0.234385 1.168188 0.061 Uiso 1 1 calc R U . . .
H15C H -0.088094 0.139146 1.137736 0.061 Uiso 1 1 calc R U . . .
C16 C 0.3141(3) 0.5875(3) 0.3214(2) 0.0340(5) Uani 1 1 d . . . . .
H16A H 0.277278 0.544556 0.266246 0.051 Uiso 1 1 calc R U . . .
H16B H 0.412935 0.610051 0.300527 0.051 Uiso 1 1 calc R U . . .
H16C H 0.250413 0.676852 0.325785 0.051 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
Sb1 Cl1 2.3589(6) . ?
Sb1 Cl1 2.3590(6) 2_667 ?
Sb1 Cl3 2.3645(6) . ?
Sb1 Cl3 2.3645(6) 2_667 ?
Sb1 Cl2 2.3667(6) . ?
Sb1 Cl2 2.3668(6) 2_667 ?
Sb2 Cl6 2.3523(6) . ?
Sb2 Cl6 2.3523(6) 2_556 ?
Sb2 Cl4 2.3631(6) . ?
Sb2 Cl4 2.3632(6) 2_556 ?
Sb2 Cl5 2.3688(5) 2_556 ?
Sb2 Cl5 2.3688(5) . ?
S1 C6 1.718(2) . ?
S1 C7 1.718(2) . ?
N1 C1 1.380(3) . ?
N1 C12 1.405(3) . ?
N1 C13 1.490(3) . ?
C13 C14 1.528(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
N1' C12 1.390(15) . ?
N1' C13' 1.490(9) . ?
N1' C1 1.498(15) . ?
C13' C14' 1.521(9) . ?
C13' H13C 0.9900 . ?
C13' H13D 0.9900 . ?
C14' H14D 0.9800 . ?
C14' H14E 0.9800 . ?
C14' H14F 0.9800 . ?
C1 C2 1.409(3) . ?
C1 C6 1.411(3) . ?
C2 C3 1.364(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.402(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.377(3) . ?
C4 C15 1.500(3) . ?
C5 C6 1.396(3) . ?
C5 H5 0.9500 . ?
C7 C8 1.403(3) . ?
C7 C12 1.413(3) . ?
C8 C9 1.375(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.406(3) . ?
C9 C16 1.494(3) . ?
C10 C11 1.365(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.410(3) . ?
C11 H11 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 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
Cl1 Sb1 Cl1 180.0 . 2_667 ?
Cl1 Sb1 Cl3 90.30(2) . . ?
Cl1 Sb1 Cl3 89.70(2) 2_667 . ?
Cl1 Sb1 Cl3 89.70(2) . 2_667 ?
Cl1 Sb1 Cl3 90.30(2) 2_667 2_667 ?
Cl3 Sb1 Cl3 180.00(3) . 2_667 ?
Cl1 Sb1 Cl2 90.09(2) . . ?
Cl1 Sb1 Cl2 89.91(2) 2_667 . ?
Cl3 Sb1 Cl2 90.20(2) . . ?
Cl3 Sb1 Cl2 89.80(2) 2_667 . ?
Cl1 Sb1 Cl2 89.91(2) . 2_667 ?
Cl1 Sb1 Cl2 90.09(2) 2_667 2_667 ?
Cl3 Sb1 Cl2 89.80(2) . 2_667 ?
Cl3 Sb1 Cl2 90.20(2) 2_667 2_667 ?
Cl2 Sb1 Cl2 180.0 . 2_667 ?
Cl6 Sb2 Cl6 180.0 . 2_556 ?
Cl6 Sb2 Cl4 90.36(3) . . ?
Cl6 Sb2 Cl4 89.65(3) 2_556 . ?
Cl6 Sb2 Cl4 89.64(3) . 2_556 ?
Cl6 Sb2 Cl4 90.35(3) 2_556 2_556 ?
Cl4 Sb2 Cl4 180.00(2) . 2_556 ?
Cl6 Sb2 Cl5 90.35(2) . 2_556 ?
Cl6 Sb2 Cl5 89.65(2) 2_556 2_556 ?
Cl4 Sb2 Cl5 89.98(2) . 2_556 ?
Cl4 Sb2 Cl5 90.02(2) 2_556 2_556 ?
Cl6 Sb2 Cl5 89.65(2) . . ?
Cl6 Sb2 Cl5 90.35(2) 2_556 . ?
Cl4 Sb2 Cl5 90.02(2) . . ?
Cl4 Sb2 Cl5 89.98(2) 2_556 . ?
Cl5 Sb2 Cl5 180.0 2_556 . ?
C6 S1 C7 102.76(11) . . ?
C1 N1 C12 123.4(2) . . ?
C1 N1 C13 118.8(2) . . ?
C12 N1 C13 117.8(2) . . ?
N1 C13 C14 112.8(2) . . ?
N1 C13 H13A 109.0 . . ?
C14 C13 H13A 109.0 . . ?
N1 C13 H13B 109.0 . . ?
C14 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
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 . . ?
C12 N1' C13' 120.9(12) . . ?
C12 N1' C1 116.2(8) . . ?
C13' N1' C1 118.9(11) . . ?
N1' C13' C14' 112.7(10) . . ?
N1' C13' H13C 109.0 . . ?
C14' C13' H13C 109.0 . . ?
N1' C13' H13D 109.0 . . ?
C14' C13' H13D 109.0 . . ?
H13C C13' H13D 107.8 . . ?
C13' C14' H14D 109.5 . . ?
C13' C14' H14E 109.5 . . ?
H14D C14' H14E 109.5 . . ?
C13' C14' H14F 109.5 . . ?
H14D C14' H14F 109.5 . . ?
H14E C14' H14F 109.5 . . ?
N1 C1 C2 120.4(2) . . ?
N1 C1 C6 122.7(2) . . ?
C2 C1 C6 116.7(2) . . ?
C2 C1 N1' 120.0(5) . . ?
C6 C1 N1' 119.8(5) . . ?
C3 C2 C1 121.3(2) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
C2 C3 C4 122.1(2) . . ?
C2 C3 H3 118.9 . . ?
C4 C3 H3 118.9 . . ?
C5 C4 C3 117.3(2) . . ?
C5 C4 C15 121.5(2) . . ?
C3 C4 C15 121.1(2) . . ?
C4 C5 C6 121.7(2) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C5 C6 C1 120.8(2) . . ?
C5 C6 S1 115.48(17) . . ?
C1 C6 S1 123.75(18) . . ?
C8 C7 C12 120.7(2) . . ?
C8 C7 S1 115.39(16) . . ?
C12 C7 S1 123.95(17) . . ?
C9 C8 C7 121.5(2) . . ?
C9 C8 H8 119.2 . . ?
C7 C8 H8 119.2 . . ?
C8 C9 C10 117.5(2) . . ?
C8 C9 C16 121.4(2) . . ?
C10 C9 C16 121.0(2) . . ?
C11 C10 C9 122.1(2) . . ?
C11 C10 H10 118.9 . . ?
C9 C10 H10 118.9 . . ?
C10 C11 C12 121.1(2) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
N1' C12 C11 116.8(6) . . ?
N1 C12 C11 121.2(2) . . ?
N1' C12 C7 122.1(5) . . ?
N1 C12 C7 121.8(2) . . ?
C11 C12 C7 116.9(2) . . ?
C4 C15 H15A 109.5 . . ?
C4 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C4 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C9 C16 H16A 109.5 . . ?
C9 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C9 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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
C1 N1 C13 C14 -88.4(3) . . . . ?
C12 N1 C13 C14 91.2(3) . . . . ?
C12 N1' C13' C14' -75.3(16) . . . . ?
C1 N1' C13' C14' 81.3(15) . . . . ?
C12 N1 C1 C2 -170.5(2) . . . . ?
C13 N1 C1 C2 9.1(4) . . . . ?
C12 N1 C1 C6 13.8(4) . . . . ?
C13 N1 C1 C6 -166.6(2) . . . . ?
C12 N1' C1 C2 163.0(6) . . . . ?
C13' N1' C1 C2 5.3(13) . . . . ?
C12 N1' C1 C6 -38.7(12) . . . . ?
C13' N1' C1 C6 163.6(8) . . . . ?
N1 C1 C2 C3 -176.1(2) . . . . ?
C6 C1 C2 C3 -0.1(3) . . . . ?
N1' C1 C2 C3 158.8(7) . . . . ?
C1 C2 C3 C4 -0.6(4) . . . . ?
C2 C3 C4 C5 1.2(3) . . . . ?
C2 C3 C4 C15 -176.6(2) . . . . ?
C3 C4 C5 C6 -1.1(3) . . . . ?
C15 C4 C5 C6 176.7(2) . . . . ?
C4 C5 C6 C1 0.4(3) . . . . ?
C4 C5 C6 S1 179.71(17) . . . . ?
N1 C1 C6 C5 176.1(2) . . . . ?
C2 C1 C6 C5 0.2(3) . . . . ?
N1' C1 C6 C5 -158.7(7) . . . . ?
N1 C1 C6 S1 -3.2(3) . . . . ?
C2 C1 C6 S1 -179.00(17) . . . . ?
N1' C1 C6 S1 22.0(7) . . . . ?
C7 S1 C6 C5 176.34(16) . . . . ?
C7 S1 C6 C1 -4.4(2) . . . . ?
C6 S1 C7 C8 -178.18(16) . . . . ?
C6 S1 C7 C12 3.0(2) . . . . ?
C12 C7 C8 C9 -1.9(3) . . . . ?
S1 C7 C8 C9 179.21(16) . . . . ?
C7 C8 C9 C10 -1.0(3) . . . . ?
C7 C8 C9 C16 179.0(2) . . . . ?
C8 C9 C10 C11 1.9(3) . . . . ?
C16 C9 C10 C11 -178.1(2) . . . . ?
C9 C10 C11 C12 0.0(3) . . . . ?
C13' N1' C12 C11 -8.2(14) . . . . ?
C1 N1' C12 C11 -165.4(6) . . . . ?
C13' N1' C12 C7 -164.6(8) . . . . ?
C1 N1' C12 C7 38.2(12) . . . . ?
C1 N1 C12 C11 168.3(2) . . . . ?
C13 N1 C12 C11 -11.3(4) . . . . ?
C1 N1 C12 C7 -15.2(4) . . . . ?
C13 N1 C12 C7 165.2(2) . . . . ?
C10 C11 C12 N1' -160.5(7) . . . . ?
C10 C11 C12 N1 173.8(2) . . . . ?
C10 C11 C12 C7 -2.9(3) . . . . ?
C8 C7 C12 N1' 160.1(7) . . . . ?
S1 C7 C12 N1' -21.1(8) . . . . ?
C8 C7 C12 N1 -172.9(2) . . . . ?
S1 C7 C12 N1 5.9(3) . . . . ?
C8 C7 C12 C11 3.8(3) . . . . ?
S1 C7 C12 C11 -177.44(16) . . . . ?

_refine_diff_density_max         1.030
_refine_diff_density_min         -0.677
_refine_diff_density_rms         0.070

