# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1051460'
_audit_update_record             
;
2015-02-27 deposited with the CCDC.
2017-01-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        SB-NS-371
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H9 F3 N2 S'
_chemical_formula_sum            'C8 H9 F3 N2 S'
_chemical_formula_weight         222.23

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 2/c'
_symmetry_space_group_name_Hall  '-P 2yc'

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

_cell_length_a                   19.392(5)
_cell_length_b                   12.369(5)
_cell_length_c                   18.099(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 110.204(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     4074(2)
_cell_formula_units_Z            16
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      3.00
_cell_measurement_theta_max      25.00

_exptl_crystal_description       block
_exptl_crystal_colour            'light yellow'
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1824
_exptl_absorpt_coefficient_mu    0.323
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9323
_exptl_absorpt_correction_T_max  0.9382
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur Sapphire'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            24995
_diffrn_reflns_av_R_equivalents  0.0832
_diffrn_reflns_av_sigmaI/netI    0.0861
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.98
_diffrn_reflns_theta_max         25.00
_reflns_number_total             6891
_reflns_number_gt                3041
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1521P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6891
_refine_ls_number_parameters     523
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.2134
_refine_ls_R_factor_gt           0.1116
_refine_ls_wR_factor_ref         0.3318
_refine_ls_wR_factor_gt          0.2682
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.1868(4) 0.2125(7) 0.6484(5) 0.113(3) Uani 1 1 d . . .
H1A H 1.2107 0.2022 0.6104 0.170 Uiso 1 1 calc R . .
H1B H 1.1367 0.1888 0.6265 0.170 Uiso 1 1 calc R . .
H1C H 1.2119 0.1711 0.6948 0.170 Uiso 1 1 calc R . .
C2 C 1.1429(3) 0.3514(5) 0.7417(4) 0.0628(16) Uani 1 1 d . . .
C3 C 1.1315(3) 0.4403(4) 0.7820(4) 0.0696(18) Uani 1 1 d . . .
C4 C 1.0948(3) 0.4036(5) 0.8286(4) 0.0673(17) Uani 1 1 d . . .
C5 C 1.0599(5) 0.4657(6) 0.8795(6) 0.100(3) Uani 1 1 d . . .
H5 H 1.0363 0.5341 0.8571 0.120 Uiso 1 1 calc R . .
C6 C 1.0260(6) 0.4095(8) 0.9252(6) 0.138(4) Uani 1 1 d . . .
H6A H 0.9822 0.4408 0.9310 0.166 Uiso 1 1 calc R . .
H6B H 1.0275 0.3312 0.9249 0.166 Uiso 1 1 calc R . .
C7 C 1.0920(7) 0.4650(10) 0.9574(8) 0.160(4) Uani 1 1 d . . .
H7A H 1.0914 0.5317 0.9854 0.192 Uiso 1 1 calc R . .
H7B H 1.1364 0.4224 0.9793 0.192 Uiso 1 1 calc R . .
C8 C 1.1546(6) 0.5538(6) 0.7766(8) 0.110(3) Uani 1 1 d . . .
C9 C 0.8410(4) 0.1597(7) 0.4971(5) 0.124(3) Uani 1 1 d . . .
H9A H 0.7950 0.1715 0.4554 0.186 Uiso 1 1 calc R . .
H9B H 0.8799 0.1923 0.4835 0.186 Uiso 1 1 calc R . .
H9C H 0.8393 0.1916 0.5448 0.186 Uiso 1 1 calc R . .
C10 C 0.9412(3) 0.0184(5) 0.5884(4) 0.0672(17) Uani 1 1 d . . .
C11 C 0.9839(3) -0.0723(4) 0.6182(4) 0.0620(15) Uani 1 1 d . . .
C12 C 1.0451(3) -0.0377(4) 0.6779(3) 0.0565(14) Uani 1 1 d . . .
C13 C 1.1087(4) -0.0983(5) 0.7299(4) 0.082(2) Uani 1 1 d . . .
H13 H 1.0971 -0.1698 0.7458 0.099 Uiso 1 1 calc R . .
C14 C 1.1706(5) -0.0431(7) 0.7887(6) 0.113(3) Uani 1 1 d . . .
H14A H 1.1688 0.0351 0.7913 0.136 Uiso 1 1 calc R . .
H14B H 1.1935 -0.0786 0.8391 0.136 Uiso 1 1 calc R . .
C15 C 1.1814(4) -0.0898(8) 0.7216(6) 0.125(3) Uani 1 1 d . . .
H15A H 1.2110 -0.1549 0.7295 0.150 Uiso 1 1 calc R . .
H15B H 1.1863 -0.0411 0.6817 0.150 Uiso 1 1 calc R . .
C16 C 0.9672(5) -0.1851(6) 0.5922(6) 0.097(3) Uani 1 1 d . . .
C17 C 1.3301(5) 0.2666(8) 0.8942(6) 0.148(4) Uani 1 1 d . . .
H17A H 1.2833 0.2818 0.8990 0.222 Uiso 1 1 calc R . .
H17B H 1.3368 0.3119 0.8542 0.222 Uiso 1 1 calc R . .
H17C H 1.3684 0.2806 0.9435 0.222 Uiso 1 1 calc R . .
C18 C 1.4216(3) 0.1159(6) 0.8634(4) 0.0790(19) Uani 1 1 d . . .
C19 C 1.4596(4) 0.0215(5) 0.8680(4) 0.087(2) Uani 1 1 d . . .
C20 C 1.5255(4) 0.0498(6) 0.8603(5) 0.090(2) Uani 1 1 d . . .
C21 C 1.5874(5) -0.0180(8) 0.8548(7) 0.126(3) Uani 1 1 d . . .
H21 H 1.5734 -0.0861 0.8258 0.151 Uiso 1 1 calc R . .
C22 C 1.6512(7) -0.0188(11) 0.9155(9) 0.177(5) Uani 1 1 d . . .
H22A H 1.6770 -0.0872 0.9282 0.212 Uiso 1 1 calc R . .
H22B H 1.6539 0.0245 0.9611 0.212 Uiso 1 1 calc R . .
C23 C 1.6544(5) 0.0355(9) 0.8501(7) 0.132(3) Uani 1 1 d . . .
H23A H 1.6799 0.0013 0.8187 0.158 Uiso 1 1 calc R . .
H23B H 1.6566 0.1138 0.8519 0.158 Uiso 1 1 calc R . .
C24 C 1.4333(6) -0.0886(9) 0.8761(9) 0.138(4) Uani 1 1 d . . .
C25 C 1.3210(7) 0.2929(9) 0.4957(5) 0.178(5) Uani 1 1 d . . .
H25A H 1.3010 0.2835 0.4396 0.267 Uiso 1 1 calc R . .
H25B H 1.2955 0.2466 0.5203 0.267 Uiso 1 1 calc R . .
H25C H 1.3723 0.2747 0.5143 0.267 Uiso 1 1 calc R . .
C26 C 1.3505(3) 0.4250(6) 0.6199(4) 0.0784(19) Uani 1 1 d . . .
C27 C 1.3522(4) 0.5123(5) 0.6684(5) 0.0771(18) Uani 1 1 d . . .
C28 C 1.3877(4) 0.4792(6) 0.7446(4) 0.081(2) Uani 1 1 d . . .
C29 C 1.4005(5) 0.5397(8) 0.8224(6) 0.129(4) Uani 1 1 d . . .
H29 H 1.3590 0.5779 0.8295 0.155 Uiso 1 1 calc R . .
C30 C 1.4655(9) 0.5741(12) 0.8597(10) 0.180(5) Uani 1 1 d . . .
H30A H 1.5003 0.5703 0.8321 0.216 Uiso 1 1 calc R . .
H30B H 1.4693 0.6402 0.8897 0.216 Uiso 1 1 calc R . .
C31 C 1.4556(8) 0.4865(10) 0.8929(6) 0.157(4) Uani 1 1 d . . .
H31A H 1.4482 0.4919 0.9431 0.188 Uiso 1 1 calc R . .
H31B H 1.4797 0.4211 0.8848 0.188 Uiso 1 1 calc R . .
C32 C 1.3248(6) 0.6244(7) 0.6441(7) 0.109(3) Uani 1 1 d . . .
N1 N 1.1159(2) 0.2621(4) 0.7626(3) 0.0606(13) Uani 1 1 d . . .
N2 N 1.0852(3) 0.2974(4) 0.8157(3) 0.0670(14) Uani 1 1 d D . .
N3 N 1.0361(3) 0.0696(4) 0.6803(4) 0.0647(14) Uani 1 1 d . . .
N4 N 0.9722(3) 0.1061(4) 0.6267(3) 0.0700(14) Uani 1 1 d . . .
N5 N 1.4590(3) 0.2018(4) 0.8520(3) 0.0759(15) Uani 1 1 d . . .
N6 N 1.5233(3) 0.1588(4) 0.8511(3) 0.0723(14) Uani 1 1 d D . .
N7 N 1.3814(3) 0.3411(4) 0.6638(4) 0.0727(14) Uani 1 1 d . . .
N8 N 1.4035(3) 0.3766(4) 0.7382(4) 0.0710(16) Uani 1 1 d . . .
F1 F 1.2228(4) 0.5681(5) 0.8029(6) 0.211(4) Uani 1 1 d . . .
F2 F 1.1414(5) 0.5863(5) 0.7042(5) 0.200(3) Uani 1 1 d . . .
F3 F 1.1261(6) 0.6226(4) 0.8038(7) 0.271(5) Uani 1 1 d . . .
F4 F 0.8985(4) -0.2109(4) 0.5757(5) 0.179(3) Uani 1 1 d . . .
F5 F 0.9730(5) -0.2025(6) 0.5260(6) 0.238(5) Uani 1 1 d . . .
F6 F 0.9995(5) -0.2553(4) 0.6400(6) 0.284(6) Uani 1 1 d . . .
F7 F 1.3734(5) -0.1083(7) 0.8484(8) 0.292(7) Uani 1 1 d . . .
F8 F 1.4685(8) -0.1595(7) 0.8572(12) 0.342(10) Uani 1 1 d . . .
F9 F 1.4541(9) -0.1145(8) 0.9484(5) 0.319(9) Uani 1 1 d . . .
F10 F 1.3523(6) 0.6699(6) 0.6003(7) 0.273(6) Uani 1 1 d . . .
F11 F 1.3283(6) 0.6891(5) 0.6974(6) 0.258(5) Uani 1 1 d . . .
F12 F 1.2575(5) 0.6267(6) 0.6053(8) 0.267(6) Uani 1 1 d . . .
S1 S 1.18915(12) 0.35129(17) 0.67326(14) 0.1052(8) Uani 1 1 d . . .
S2 S 0.85709(11) 0.02053(17) 0.51113(14) 0.1128(9) Uani 1 1 d . . .
S3 S 1.33329(12) 0.1301(2) 0.86834(19) 0.1406(11) Uani 1 1 d . . .
S4 S 1.31067(16) 0.4238(2) 0.51840(14) 0.1400(11) Uani 1 1 d . . .
H2' H 1.077(5) 0.238(5) 0.845(5) 0.18(4) Uiso 1 1 d D . .
H3A H 1.066(3) 0.107(4) 0.714(3) 0.047(16) Uiso 1 1 d . . .
H6D H 1.568(4) 0.187(10) 0.846(7) 0.24(6) Uiso 1 1 d D . .
H8A H 1.416(3) 0.339(4) 0.779(3) 0.045(16) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 S1 1.772(8) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 N1 1.332(7) . ?
C2 C3 1.379(8) . ?
C2 S1 1.762(6) . ?
C3 C4 1.356(8) . ?
C3 C8 1.487(9) . ?
C4 N2 1.336(7) . ?
C4 C5 1.526(10) . ?
C5 C7 1.329(12) . ?
C5 C6 1.404(11) . ?
C5 H5 0.9800 . ?
C6 C7 1.390(12) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 F3 1.207(9) . ?
C8 F1 1.255(10) . ?
C8 F2 1.310(11) . ?
C9 S2 1.752(8) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 N4 1.315(7) . ?
C10 C11 1.388(8) . ?
C10 S2 1.743(6) . ?
C11 C12 1.369(8) . ?
C11 C16 1.471(9) . ?
C12 N3 1.341(7) . ?
C12 C13 1.473(8) . ?
C13 C14 1.469(10) . ?
C13 C15 1.473(10) . ?
C13 H13 0.9800 . ?
C14 C15 1.425(11) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 F6 1.233(9) . ?
C16 F5 1.260(10) . ?
C16 F4 1.301(9) . ?
C17 S3 1.759(10) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 N5 1.342(8) . ?
C18 C19 1.367(9) . ?
C18 S3 1.755(7) . ?
C19 C20 1.380(9) . ?
C19 C24 1.479(12) . ?
C20 N6 1.357(8) . ?
C20 C21 1.494(11) . ?
C21 C22 1.342(14) . ?
C21 C23 1.486(13) . ?
C21 H21 0.9800 . ?
C22 C23 1.380(14) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 F7 1.122(11) . ?
C24 F8 1.229(14) . ?
C24 F9 1.271(13) . ?
C25 S4 1.699(10) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 N7 1.319(8) . ?
C26 C27 1.385(9) . ?
C26 S4 1.729(8) . ?
C27 C28 1.373(9) . ?
C27 C32 1.496(10) . ?
C28 N8 1.318(8) . ?
C28 C29 1.538(11) . ?
C29 C30 1.280(14) . ?
C29 C31 1.503(13) . ?
C29 H29 0.9800 . ?
C30 C31 1.284(15) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 F10 1.233(11) . ?
C32 F11 1.238(11) . ?
C32 F12 1.251(11) . ?
N1 N2 1.365(6) . ?
N2 H2' 0.95(2) . ?
N3 N4 1.361(7) . ?
N3 H3A 0.83(5) . ?
N5 N6 1.361(7) . ?
N6 H6D 0.96(2) . ?
N7 N8 1.339(7) . ?
N8 H8A 0.84(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
S1 C1 H1A 109.5 . . ?
S1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
S1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C3 111.1(5) . . ?
N1 C2 S1 123.0(4) . . ?
C3 C2 S1 125.9(5) . . ?
C4 C3 C2 106.1(5) . . ?
C4 C3 C8 126.2(6) . . ?
C2 C3 C8 127.7(6) . . ?
N2 C4 C3 107.0(5) . . ?
N2 C4 C5 122.4(6) . . ?
C3 C4 C5 130.2(6) . . ?
C7 C5 C6 61.1(7) . . ?
C7 C5 C4 119.6(9) . . ?
C6 C5 C4 120.1(7) . . ?
C7 C5 H5 115.1 . . ?
C6 C5 H5 115.1 . . ?
C4 C5 H5 115.1 . . ?
C7 C6 C5 56.8(6) . . ?
C7 C6 H6A 118.1 . . ?
C5 C6 H6A 118.1 . . ?
C7 C6 H6B 118.1 . . ?
C5 C6 H6B 118.1 . . ?
H6A C6 H6B 115.3 . . ?
C5 C7 C6 62.1(7) . . ?
C5 C7 H7A 117.6 . . ?
C6 C7 H7A 117.6 . . ?
C5 C7 H7B 117.6 . . ?
C6 C7 H7B 117.6 . . ?
H7A C7 H7B 114.6 . . ?
F3 C8 F1 108.5(11) . . ?
F3 C8 F2 103.5(10) . . ?
F1 C8 F2 98.7(8) . . ?
F3 C8 C3 116.7(7) . . ?
F1 C8 C3 114.2(8) . . ?
F2 C8 C3 113.3(9) . . ?
S2 C9 H9A 109.5 . . ?
S2 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
S2 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N4 C10 C11 111.0(6) . . ?
N4 C10 S2 122.8(5) . . ?
C11 C10 S2 126.2(5) . . ?
C12 C11 C10 107.0(5) . . ?
C12 C11 C16 125.7(6) . . ?
C10 C11 C16 127.3(6) . . ?
C11 C12 N3 104.4(5) . . ?
C11 C12 C13 130.7(5) . . ?
N3 C12 C13 124.9(5) . . ?
C14 C13 C15 58.0(5) . . ?
C14 C13 C12 121.4(6) . . ?
C15 C13 C12 121.2(6) . . ?
C14 C13 H13 114.8 . . ?
C15 C13 H13 114.8 . . ?
C12 C13 H13 114.8 . . ?
C15 C14 C13 61.2(5) . . ?
C15 C14 H14A 117.7 . . ?
C13 C14 H14A 117.7 . . ?
C15 C14 H14B 117.7 . . ?
C13 C14 H14B 117.7 . . ?
H14A C14 H14B 114.8 . . ?
C14 C15 C13 60.9(5) . . ?
C14 C15 H15A 117.7 . . ?
C13 C15 H15A 117.7 . . ?
C14 C15 H15B 117.7 . . ?
C13 C15 H15B 117.7 . . ?
H15A C15 H15B 114.8 . . ?
F6 C16 F5 110.8(9) . . ?
F6 C16 F4 102.7(9) . . ?
F5 C16 F4 99.2(8) . . ?
F6 C16 C11 116.2(7) . . ?
F5 C16 C11 112.6(8) . . ?
F4 C16 C11 113.7(6) . . ?
S3 C17 H17A 109.5 . . ?
S3 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
S3 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N5 C18 C19 112.2(6) . . ?
N5 C18 S3 121.1(6) . . ?
C19 C18 S3 126.6(5) . . ?
C18 C19 C20 106.0(6) . . ?
C18 C19 C24 126.6(8) . . ?
C20 C19 C24 127.4(8) . . ?
N6 C20 C19 105.9(6) . . ?
N6 C20 C21 122.8(7) . . ?
C19 C20 C21 131.1(7) . . ?
C22 C21 C23 58.2(7) . . ?
C22 C21 C20 119.0(10) . . ?
C23 C21 C20 119.4(8) . . ?
C22 C21 H21 116.0 . . ?
C23 C21 H21 116.0 . . ?
C20 C21 H21 116.0 . . ?
C21 C22 C23 66.2(9) . . ?
C21 C22 H22A 117.1 . . ?
C23 C22 H22A 117.1 . . ?
C21 C22 H22B 117.1 . . ?
C23 C22 H22B 117.1 . . ?
H22A C22 H22B 114.1 . . ?
C22 C23 C21 55.7(7) . . ?
C22 C23 H23A 118.2 . . ?
C21 C23 H23A 118.2 . . ?
C22 C23 H23B 118.2 . . ?
C21 C23 H23B 118.2 . . ?
H23A C23 H23B 115.4 . . ?
F7 C24 F8 108.0(17) . . ?
F7 C24 F9 108.5(12) . . ?
F8 C24 F9 95.6(11) . . ?
F7 C24 C19 119.6(9) . . ?
F8 C24 C19 112.8(9) . . ?
F9 C24 C19 109.6(12) . . ?
S4 C25 H25A 109.5 . . ?
S4 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
S4 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
N7 C26 C27 108.9(7) . . ?
N7 C26 S4 125.2(6) . . ?
C27 C26 S4 125.8(6) . . ?
C28 C27 C26 107.3(6) . . ?
C28 C27 C32 125.2(7) . . ?
C26 C27 C32 127.4(8) . . ?
N8 C28 C27 104.5(6) . . ?
N8 C28 C29 125.4(7) . . ?
C27 C28 C29 129.8(7) . . ?
C30 C29 C31 54.3(7) . . ?
C30 C29 C28 117.6(11) . . ?
C31 C29 C28 114.0(7) . . ?
C30 C29 H29 118.3 . . ?
C31 C29 H29 118.3 . . ?
C28 C29 H29 118.3 . . ?
C31 C30 C29 71.8(10) . . ?
C31 C30 H30A 116.4 . . ?
C29 C30 H30A 116.4 . . ?
C31 C30 H30B 116.4 . . ?
C29 C30 H30B 116.4 . . ?
H30A C30 H30B 113.4 . . ?
C30 C31 C29 54.0(8) . . ?
C30 C31 H31A 118.3 . . ?
C29 C31 H31A 118.3 . . ?
C30 C31 H31B 118.3 . . ?
C29 C31 H31B 118.3 . . ?
H31A C31 H31B 115.6 . . ?
F10 C32 F11 106.6(10) . . ?
F10 C32 F12 103.3(11) . . ?
F11 C32 F12 100.8(10) . . ?
F10 C32 C27 115.1(9) . . ?
F11 C32 C27 116.8(9) . . ?
F12 C32 C27 112.4(8) . . ?
C2 N1 N2 104.2(4) . . ?
C4 N2 N1 111.7(5) . . ?
C4 N2 H2' 135(6) . . ?
N1 N2 H2' 110(6) . . ?
C12 N3 N4 113.6(5) . . ?
C12 N3 H3A 121(3) . . ?
N4 N3 H3A 126(3) . . ?
C10 N4 N3 103.9(5) . . ?
C18 N5 N6 103.8(5) . . ?
C20 N6 N5 112.2(5) . . ?
C20 N6 H6D 112(8) . . ?
N5 N6 H6D 135(8) . . ?
C26 N7 N8 105.6(6) . . ?
C28 N8 N7 113.6(6) . . ?
C28 N8 H8A 117(3) . . ?
N7 N8 H8A 127(4) . . ?
C2 S1 C1 101.8(3) . . ?
C10 S2 C9 101.6(3) . . ?
C18 S3 C17 103.6(4) . . ?
C25 S4 C26 102.6(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C3 C4 -1.0(8) . . . . ?
S1 C2 C3 C4 -179.3(5) . . . . ?
N1 C2 C3 C8 178.7(8) . . . . ?
S1 C2 C3 C8 0.4(11) . . . . ?
C2 C3 C4 N2 -0.1(7) . . . . ?
C8 C3 C4 N2 -179.8(8) . . . . ?
C2 C3 C4 C5 -172.5(7) . . . . ?
C8 C3 C4 C5 7.8(13) . . . . ?
N2 C4 C5 C7 82.2(10) . . . . ?
C3 C4 C5 C7 -106.4(10) . . . . ?
N2 C4 C5 C6 10.4(13) . . . . ?
C3 C4 C5 C6 -178.2(9) . . . . ?
C4 C5 C6 C7 109.4(11) . . . . ?
C4 C5 C7 C6 -110.2(8) . . . . ?
C4 C3 C8 F3 -15.5(16) . . . . ?
C2 C3 C8 F3 164.8(10) . . . . ?
C4 C3 C8 F1 112.5(10) . . . . ?
C2 C3 C8 F1 -67.2(14) . . . . ?
C4 C3 C8 F2 -135.5(8) . . . . ?
C2 C3 C8 F2 44.8(13) . . . . ?
N4 C10 C11 C12 -0.6(7) . . . . ?
S2 C10 C11 C12 179.7(4) . . . . ?
N4 C10 C11 C16 178.7(7) . . . . ?
S2 C10 C11 C16 -1.0(11) . . . . ?
C10 C11 C12 N3 -0.2(6) . . . . ?
C16 C11 C12 N3 -179.5(7) . . . . ?
C10 C11 C12 C13 180.0(6) . . . . ?
C16 C11 C12 C13 0.7(11) . . . . ?
C11 C12 C13 C14 177.4(7) . . . . ?
N3 C12 C13 C14 -2.3(10) . . . . ?
C11 C12 C13 C15 108.3(9) . . . . ?
N3 C12 C13 C15 -71.4(9) . . . . ?
C12 C13 C14 C15 -109.5(8) . . . . ?
C12 C13 C15 C14 109.9(8) . . . . ?
C12 C11 C16 F6 20.5(14) . . . . ?
C10 C11 C16 F6 -158.6(9) . . . . ?
C12 C11 C16 F5 -108.8(9) . . . . ?
C10 C11 C16 F5 72.0(11) . . . . ?
C12 C11 C16 F4 139.4(7) . . . . ?
C10 C11 C16 F4 -39.7(13) . . . . ?
N5 C18 C19 C20 0.9(9) . . . . ?
S3 C18 C19 C20 179.3(6) . . . . ?
N5 C18 C19 C24 -176.6(9) . . . . ?
S3 C18 C19 C24 1.8(13) . . . . ?
C18 C19 C20 N6 -0.3(8) . . . . ?
C24 C19 C20 N6 177.2(10) . . . . ?
C18 C19 C20 C21 -175.0(9) . . . . ?
C24 C19 C20 C21 2.5(16) . . . . ?
N6 C20 C21 C22 76.4(13) . . . . ?
C19 C20 C21 C22 -109.7(12) . . . . ?
N6 C20 C21 C23 8.7(14) . . . . ?
C19 C20 C21 C23 -177.3(10) . . . . ?
C20 C21 C22 C23 -108.5(10) . . . . ?
C20 C21 C23 C22 107.7(12) . . . . ?
C18 C19 C24 F7 32(2) . . . . ?
C20 C19 C24 F7 -144.7(14) . . . . ?
C18 C19 C24 F8 160.9(14) . . . . ?
C20 C19 C24 F8 -16(2) . . . . ?
C18 C19 C24 F9 -93.9(14) . . . . ?
C20 C19 C24 F9 89.2(16) . . . . ?
N7 C26 C27 C28 1.8(8) . . . . ?
S4 C26 C27 C28 179.0(5) . . . . ?
N7 C26 C27 C32 178.6(7) . . . . ?
S4 C26 C27 C32 -4.2(11) . . . . ?
C26 C27 C28 N8 -1.3(7) . . . . ?
C32 C27 C28 N8 -178.3(7) . . . . ?
C26 C27 C28 C29 -175.3(8) . . . . ?
C32 C27 C28 C29 7.7(13) . . . . ?
N8 C28 C29 C30 80.5(16) . . . . ?
C27 C28 C29 C30 -106.6(13) . . . . ?
N8 C28 C29 C31 19.8(15) . . . . ?
C27 C28 C29 C31 -167.4(10) . . . . ?
C28 C29 C30 C31 -100.9(12) . . . . ?
C28 C29 C31 C30 107.8(14) . . . . ?
C28 C27 C32 F10 119.0(12) . . . . ?
C26 C27 C32 F10 -57.3(14) . . . . ?
C28 C27 C32 F11 -7.3(15) . . . . ?
C26 C27 C32 F11 176.4(10) . . . . ?
C28 C27 C32 F12 -123.1(11) . . . . ?
C26 C27 C32 F12 60.5(14) . . . . ?
C3 C2 N1 N2 1.6(7) . . . . ?
S1 C2 N1 N2 180.0(4) . . . . ?
C3 C4 N2 N1 1.1(7) . . . . ?
C5 C4 N2 N1 174.3(6) . . . . ?
C2 N1 N2 C4 -1.7(7) . . . . ?
C11 C12 N3 N4 1.0(6) . . . . ?
C13 C12 N3 N4 -179.2(6) . . . . ?
C11 C10 N4 N3 1.1(7) . . . . ?
S2 C10 N4 N3 -179.2(4) . . . . ?
C12 N3 N4 C10 -1.3(6) . . . . ?
C19 C18 N5 N6 -1.2(8) . . . . ?
S3 C18 N5 N6 -179.6(5) . . . . ?
C19 C20 N6 N5 -0.5(8) . . . . ?
C21 C20 N6 N5 174.8(7) . . . . ?
C18 N5 N6 C20 1.0(7) . . . . ?
C27 C26 N7 N8 -1.4(7) . . . . ?
S4 C26 N7 N8 -178.7(5) . . . . ?
C27 C28 N8 N7 0.5(8) . . . . ?
C29 C28 N8 N7 174.8(7) . . . . ?
C26 N7 N8 C28 0.6(7) . . . . ?
N1 C2 S1 C1 -0.4(6) . . . . ?
C3 C2 S1 C1 177.7(6) . . . . ?
N4 C10 S2 C9 7.6(7) . . . . ?
C11 C10 S2 C9 -172.7(6) . . . . ?
N5 C18 S3 C17 -22.2(7) . . . . ?
C19 C18 S3 C17 159.6(7) . . . . ?
N7 C26 S4 C25 1.2(8) . . . . ?
C27 C26 S4 C25 -175.6(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.959
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.959
_refine_diff_density_max         0.417
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.072
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DCM, Hexane'
####################################################################### 
# 
# 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_shelxl
_audit_block_doi                 10.5517/cc1494zk
_database_code_depnum_ccdc_archive 'CCDC 1051488'
_audit_update_record             
;
2015-02-27 deposited with the CCDC.
2017-01-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        SB-NS-357
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H11 F3 O2 S2'
_chemical_formula_sum            'C14 H11 F3 O2 S2'
_chemical_formula_weight         332.35

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'

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

_cell_length_a                   13.456(5)
_cell_length_b                   10.034(5)
_cell_length_c                   22.429(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 90.000(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     3028(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            'light yellow'
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1360
_exptl_absorpt_coefficient_mu    0.383
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9204
_exptl_absorpt_correction_T_max  0.9342
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9837
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_av_sigmaI/netI    0.0236
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.12
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2653
_reflns_number_gt                2233
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0526P)²+1.1820P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2653
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0470
_refine_ls_wR_factor_ref         0.1175
_refine_ls_wR_factor_gt          0.1121
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.087
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.002

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.39220(17) 0.0429(2) 0.06894(10) 0.0436(6) Uani 1 1 d . . .
C2 C 0.31711(19) -0.0398(3) 0.04880(11) 0.0553(7) Uani 1 1 d . . .
H2 H 0.2535 -0.0080 0.0409 0.066 Uiso 1 1 calc R . .
C3 C 0.3416(2) -0.1712(3) 0.04110(12) 0.0636(8) Uani 1 1 d . . .
H3 H 0.2934 -0.2302 0.0275 0.076 Uiso 1 1 calc R . .
C4 C 0.4370(2) -0.2190(3) 0.05304(13) 0.0666(8) Uani 1 1 d . . .
H4 H 0.4508 -0.3089 0.0471 0.080 Uiso 1 1 calc R . .
C5 C 0.5110(2) -0.1359(3) 0.07341(13) 0.0596(7) Uani 1 1 d . . .
H5 H 0.5744 -0.1684 0.0814 0.071 Uiso 1 1 calc R . .
C6 C 0.48819(17) -0.0012(2) 0.08180(11) 0.0446(6) Uani 1 1 d . . .
C7 C 0.54013(17) 0.1142(2) 0.10262(11) 0.0445(6) Uani 1 1 d . . .
H7 H 0.6061 0.1179 0.1149 0.053 Uiso 1 1 calc R . .
C8 C 0.47527(16) 0.2166(2) 0.10107(10) 0.0411(5) Uani 1 1 d . . .
C9 C 0.48714(17) 0.3582(2) 0.11484(11) 0.0427(6) Uani 1 1 d . . .
C10 C 0.58674(16) 0.3965(2) 0.14073(10) 0.0395(5) Uani 1 1 d . . .
C11 C 0.6556(2) 0.4685(3) 0.09893(13) 0.0576(7) Uani 1 1 d . . .
C12 C 0.60928(17) 0.3688(2) 0.19752(11) 0.0437(6) Uani 1 1 d . . .
C13 C 0.7119(3) 0.4556(5) 0.29822(16) 0.1155(15) Uani 1 1 d . . .
H13A H 0.7749 0.4677 0.3176 0.173 Uiso 1 1 calc R . .
H13B H 0.6712 0.3971 0.3217 0.173 Uiso 1 1 calc R . .
H13C H 0.6794 0.5403 0.2941 0.173 Uiso 1 1 calc R . .
C14 C 0.5584(3) 0.1737(3) 0.28122(17) 0.1013(13) Uani 1 1 d . . .
H14A H 0.5090 0.1389 0.3079 0.152 Uiso 1 1 calc R . .
H14B H 0.6168 0.1972 0.3035 0.152 Uiso 1 1 calc R . .
H14C H 0.5750 0.1073 0.2521 0.152 Uiso 1 1 calc R . .
O1 O 0.38314(11) 0.17708(16) 0.08027(7) 0.0474(4) Uani 1 1 d . . .
O2 O 0.42335(14) 0.44120(18) 0.10489(9) 0.0655(5) Uani 1 1 d . . .
F1 F 0.61353(13) 0.4879(2) 0.04588(8) 0.0875(6) Uani 1 1 d . . .
F2 F 0.68242(17) 0.58812(18) 0.11837(9) 0.0982(7) Uani 1 1 d . . .
F3 F 0.73940(13) 0.4028(2) 0.08879(9) 0.0936(7) Uani 1 1 d . . .
S1 S 0.51059(5) 0.31920(7) 0.24436(3) 0.0580(2) Uani 1 1 d . . .
S2 S 0.73093(5) 0.38398(9) 0.22588(4) 0.0722(3) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.376(3) . ?
C1 C2 1.383(3) . ?
C1 C6 1.395(3) . ?
C2 C3 1.369(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.396(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.377(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.399(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.431(3) . ?
C7 C8 1.348(3) . ?
C7 H7 0.9300 . ?
C8 O1 1.383(3) . ?
C8 C9 1.463(3) . ?
C9 O2 1.217(3) . ?
C9 C10 1.510(3) . ?
C10 C12 1.338(3) . ?
C10 C11 1.503(3) . ?
C11 F2 1.327(3) . ?
C11 F3 1.326(3) . ?
C11 F1 1.332(3) . ?
C12 S2 1.763(2) . ?
C12 S1 1.765(2) . ?
C13 S2 1.793(4) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 S1 1.797(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

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
O1 C1 C2 125.6(2) . . ?
O1 C1 C6 110.7(2) . . ?
C2 C1 C6 123.6(2) . . ?
C3 C2 C1 116.3(2) . . ?
C3 C2 H2 121.9 . . ?
C1 C2 H2 121.9 . . ?
C2 C3 C4 121.9(2) . . ?
C2 C3 H3 119.0 . . ?
C4 C3 H3 119.0 . . ?
C5 C4 C3 121.3(3) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C4 C5 C6 118.1(3) . . ?
C4 C5 H5 120.9 . . ?
C6 C5 H5 120.9 . . ?
C1 C6 C5 118.8(2) . . ?
C1 C6 C7 105.3(2) . . ?
C5 C6 C7 135.9(2) . . ?
C8 C7 C6 107.0(2) . . ?
C8 C7 H7 126.5 . . ?
C6 C7 H7 126.5 . . ?
C7 C8 O1 111.8(2) . . ?
C7 C8 C9 131.6(2) . . ?
O1 C8 C9 116.60(19) . . ?
O2 C9 C8 123.3(2) . . ?
O2 C9 C10 121.5(2) . . ?
C8 C9 C10 115.2(2) . . ?
C12 C10 C11 123.6(2) . . ?
C12 C10 C9 121.0(2) . . ?
C11 C10 C9 115.4(2) . . ?
F2 C11 F3 106.0(2) . . ?
F2 C11 F1 106.1(2) . . ?
F3 C11 F1 106.3(2) . . ?
F2 C11 C10 113.4(2) . . ?
F3 C11 C10 113.1(2) . . ?
F1 C11 C10 111.4(2) . . ?
C10 C12 S2 122.42(18) . . ?
C10 C12 S1 117.03(18) . . ?
S2 C12 S1 120.55(15) . . ?
S2 C13 H13A 109.5 . . ?
S2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
S2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
S1 C14 H14A 109.5 . . ?
S1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
S1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C1 O1 C8 105.28(17) . . ?
C12 S1 C14 103.50(16) . . ?
C12 S2 C13 103.21(15) . . ?

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
O1 C1 C2 C3 -179.2(2) . . . . ?
C6 C1 C2 C3 -0.6(4) . . . . ?
C1 C2 C3 C4 0.1(4) . . . . ?
C2 C3 C4 C5 0.2(5) . . . . ?
C3 C4 C5 C6 -0.1(4) . . . . ?
O1 C1 C6 C5 179.5(2) . . . . ?
C2 C1 C6 C5 0.7(4) . . . . ?
O1 C1 C6 C7 0.4(3) . . . . ?
C2 C1 C6 C7 -178.3(2) . . . . ?
C4 C5 C6 C1 -0.3(4) . . . . ?
C4 C5 C6 C7 178.4(3) . . . . ?
C1 C6 C7 C8 -0.1(3) . . . . ?
C5 C6 C7 C8 -178.9(3) . . . . ?
C6 C7 C8 O1 -0.2(3) . . . . ?
C6 C7 C8 C9 -177.3(2) . . . . ?
C7 C8 C9 O2 171.6(3) . . . . ?
O1 C8 C9 O2 -5.4(4) . . . . ?
C7 C8 C9 C10 -6.3(4) . . . . ?
O1 C8 C9 C10 176.66(19) . . . . ?
O2 C9 C10 C12 106.5(3) . . . . ?
C8 C9 C10 C12 -75.5(3) . . . . ?
O2 C9 C10 C11 -72.4(3) . . . . ?
C8 C9 C10 C11 105.6(2) . . . . ?
C12 C10 C11 F2 -57.8(3) . . . . ?
C9 C10 C11 F2 121.0(3) . . . . ?
C12 C10 C11 F3 62.9(3) . . . . ?
C9 C10 C11 F3 -118.3(3) . . . . ?
C12 C10 C11 F1 -177.5(2) . . . . ?
C9 C10 C11 F1 1.4(3) . . . . ?
C11 C10 C12 S2 -12.9(3) . . . . ?
C9 C10 C12 S2 168.35(17) . . . . ?
C11 C10 C12 S1 165.76(19) . . . . ?
C9 C10 C12 S1 -13.0(3) . . . . ?
C2 C1 O1 C8 178.2(2) . . . . ?
C6 C1 O1 C8 -0.5(2) . . . . ?
C7 C8 O1 C1 0.5(3) . . . . ?
C9 C8 O1 C1 178.0(2) . . . . ?
C10 C12 S1 C14 132.2(2) . . . . ?
S2 C12 S1 C14 -49.2(2) . . . . ?
C10 C12 S2 C13 139.3(2) . . . . ?
S1 C12 S2 C13 -39.2(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.036
_exptl_crystal_recrystallization_method 'Vapour Deposition'
