# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_cd15290
_database_code_depnum_ccdc_archive 'CCDC 1439307'
_audit_update_record             
;
2015-11-27 deposited with the CCDC.
2016-06-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H16 F3 N S'
_chemical_formula_weight         323.37

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                   9.8932(13)
_cell_length_b                   15.009(2)
_cell_length_c                   21.270(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3158.2(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2698
_cell_measurement_theta_min      4.541
_cell_measurement_theta_max      40.524

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_F_000             1344
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.231
_shelx_estimated_absorpt_T_min   0.951
_shelx_estimated_absorpt_T_max   0.977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5881
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18275
_diffrn_reflns_av_unetI/netI     0.0597
_diffrn_reflns_av_R_equivalents  0.0582
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.661
_diffrn_reflns_theta_max         25.493
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5871
_reflns_number_gt                4591
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.773
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0540P)²+0.0065P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1541 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -0.01(5)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         5871
_refine_ls_number_parameters     407
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0720
_refine_ls_R_factor_gt           0.0539
_refine_ls_wR_factor_ref         0.1186
_refine_ls_wR_factor_gt          0.1106
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_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 0.38375(12) 0.71450(8) 0.84809(5) 0.0473(3) Uani 1 1 d . . . . .
S2 S 0.83315(13) 0.60486(8) 0.74078(6) 0.0572(4) Uani 1 1 d . . . . .
F1 F 0.6155(3) 0.7679(2) 0.81618(15) 0.0850(10) Uani 1 1 d . . . . .
F2 F 0.6236(3) 0.66214(19) 0.88334(17) 0.0821(10) Uani 1 1 d . . . . .
F3 F 0.5748(3) 0.79195(19) 0.91305(15) 0.0718(8) Uani 1 1 d . . . . .
F4 F 0.9058(5) 0.6338(3) 0.6254(2) 0.1290(17) Uani 1 1 d . . . . .
F5 F 1.0605(4) 0.5841(2) 0.6816(2) 0.1062(13) Uani 1 1 d . . . . .
F6 F 0.9914(5) 0.7174(2) 0.6948(2) 0.1292(16) Uani 1 1 d . . . . .
N1 N 0.1066(5) 0.6640(3) 0.8759(2) 0.0580(12) Uani 1 1 d . . . . .
N2 N 0.6260(5) 0.4884(3) 0.7934(2) 0.0488(10) Uani 1 1 d . . . . .
C1 C 0.0683(5) 0.7482(3) 0.8966(2) 0.0514(12) Uani 1 1 d . . . . .
C2 C -0.0483(5) 0.7874(3) 0.8734(2) 0.0625(13) Uani 1 1 d . . . . .
H2 H -0.1025 0.7559 0.8455 0.075 Uiso 1 1 calc R U . . .
C3 C -0.0848(6) 0.8719(4) 0.8911(3) 0.0732(16) Uani 1 1 d . . . . .
H3 H -0.1634 0.8973 0.8751 0.088 Uiso 1 1 calc R U . . .
C4 C -0.0057(7) 0.9192(3) 0.9322(3) 0.0702(16) Uani 1 1 d . . . . .
H4 H -0.0303 0.9765 0.9443 0.084 Uiso 1 1 calc R U . . .
C5 C 0.1104(6) 0.8809(3) 0.9556(2) 0.0620(14) Uani 1 1 d . . . . .
H5 H 0.1640 0.9131 0.9834 0.074 Uiso 1 1 calc R U . . .
C6 C 0.1489(5) 0.7957(3) 0.9387(2) 0.0479(11) Uani 1 1 d . . . . .
C7 C 0.2753(5) 0.7548(3) 0.9649(2) 0.0541(12) Uani 1 1 d . . . . .
H7A H 0.2580 0.7340 1.0073 0.065 Uiso 1 1 calc R U . . .
H7B H 0.3457 0.7996 0.9669 0.065 Uiso 1 1 calc R U . . .
C8 C 0.3237(5) 0.6767(3) 0.9246(2) 0.0462(11) Uani 1 1 d . . . . .
H8 H 0.3960 0.6446 0.9465 0.055 Uiso 1 1 calc R U . . .
C9 C 0.2034(5) 0.6139(3) 0.9132(2) 0.0508(12) Uani 1 1 d . . . . .
H9 H 0.1616 0.6013 0.9540 0.061 Uiso 1 1 calc R U . . .
C10 C 0.2396(5) 0.5262(3) 0.8834(2) 0.0503(12) Uani 1 1 d . . . . .
C11 C 0.2730(5) 0.4561(3) 0.9217(3) 0.0575(13) Uani 1 1 d . . . . .
H11 H 0.2717 0.4644 0.9650 0.069 Uiso 1 1 calc R U . . .
C12 C 0.3086(5) 0.3731(3) 0.8983(3) 0.0644(15) Uani 1 1 d . . . . .
C13 C 0.3083(5) 0.3622(4) 0.8337(3) 0.0718(17) Uani 1 1 d . . . . .
H13 H 0.3294 0.3069 0.8166 0.086 Uiso 1 1 calc R U . . .
C14 C 0.2776(6) 0.4310(3) 0.7949(3) 0.0659(15) Uani 1 1 d . . . . .
H14 H 0.2800 0.4224 0.7516 0.079 Uiso 1 1 calc R U . . .
C15 C 0.2430(5) 0.5136(3) 0.8185(3) 0.0581(13) Uani 1 1 d . . . . .
H15 H 0.2223 0.5602 0.7914 0.070 Uiso 1 1 calc R U . . .
C16 C 0.3431(8) 0.2968(4) 0.9417(4) 0.110(2) Uani 1 1 d . . . . .
H16A H 0.3166 0.2416 0.9226 0.164 Uiso 1 1 calc R U . . .
H16B H 0.2959 0.3042 0.9808 0.164 Uiso 1 1 calc R U . . .
H16C H 0.4387 0.2963 0.9494 0.164 Uiso 1 1 calc R U . . .
C17 C 0.5566(5) 0.7340(3) 0.8669(2) 0.0534(12) Uani 1 1 d . . . . .
C18 C 0.7077(5) 0.4539(3) 0.8406(2) 0.0418(11) Uani 1 1 d . . . . .
C19 C 0.6622(6) 0.4508(3) 0.9019(2) 0.0530(12) Uani 1 1 d . . . . .
H19 H 0.5753 0.4703 0.9112 0.064 Uiso 1 1 calc R U . . .
C20 C 0.7438(7) 0.4190(3) 0.9495(2) 0.0663(16) Uani 1 1 d . . . . .
H20 H 0.7114 0.4166 0.9905 0.080 Uiso 1 1 calc R U . . .
C21 C 0.8717(6) 0.3912(3) 0.9363(3) 0.0697(15) Uani 1 1 d . . . . .
H21 H 0.9269 0.3694 0.9682 0.084 Uiso 1 1 calc R U . . .
C22 C 0.9187(5) 0.3957(3) 0.8757(3) 0.0582(13) Uani 1 1 d . . . . .
H22 H 1.0070 0.3780 0.8672 0.070 Uiso 1 1 calc R U . . .
C23 C 0.8386(5) 0.4257(3) 0.8269(2) 0.0463(11) Uani 1 1 d . . . . .
C24 C 0.8895(5) 0.4257(3) 0.7600(2) 0.0530(12) Uani 1 1 d . . . . .
H24A H 0.8852 0.3657 0.7433 0.064 Uiso 1 1 calc R U . . .
H24B H 0.9833 0.4446 0.7594 0.064 Uiso 1 1 calc R U . . .
C25 C 0.8063(5) 0.4875(3) 0.7189(2) 0.0456(11) Uani 1 1 d . . . . .
H25 H 0.8307 0.4786 0.6747 0.055 Uiso 1 1 calc R U . . .
C26 C 0.6567(5) 0.4676(3) 0.7281(2) 0.0417(11) Uani 1 1 d . . . . .
H26 H 0.6437 0.4034 0.7223 0.050 Uiso 1 1 calc R U . . .
C27 C 0.5663(5) 0.5145(3) 0.6826(2) 0.0431(10) Uani 1 1 d . . . . .
C28 C 0.5536(6) 0.4797(3) 0.6228(2) 0.0590(14) Uani 1 1 d . . . . .
H28 H 0.5999 0.4279 0.6122 0.071 Uiso 1 1 calc R U . . .
C29 C 0.4729(7) 0.5209(4) 0.5786(3) 0.0790(18) Uani 1 1 d . . . . .
H29 H 0.4650 0.4968 0.5385 0.095 Uiso 1 1 calc R U . . .
C30 C 0.4047(6) 0.5970(3) 0.5939(2) 0.0696(16) Uani 1 1 d . . . . .
H30 H 0.3494 0.6241 0.5641 0.083 Uiso 1 1 calc R U . . .
C31 C 0.4168(5) 0.6340(3) 0.6528(2) 0.0524(12) Uani 1 1 d . . . . .
C32 C 0.4970(5) 0.5921(3) 0.6963(2) 0.0467(11) Uani 1 1 d . . . . .
H32 H 0.5049 0.6166 0.7363 0.056 Uiso 1 1 calc R U . . .
C33 C 0.3427(6) 0.7195(3) 0.6694(3) 0.0751(16) Uani 1 1 d . . . . .
H33A H 0.4072 0.7650 0.6797 0.113 Uiso 1 1 calc R U . . .
H33B H 0.2846 0.7091 0.7048 0.113 Uiso 1 1 calc R U . . .
H33C H 0.2895 0.7384 0.6341 0.113 Uiso 1 1 calc R U . . .
C34 C 0.9510(7) 0.6356(4) 0.6828(4) 0.0778(17) Uani 1 1 d . . . . .
H2A H 0.559(5) 0.485(3) 0.800(2) 0.037(16) Uiso 1 1 d . . . . .
H1 H 0.046(6) 0.632(3) 0.864(2) 0.067(17) 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
S1 C17 1.781(5) . ?
S1 C8 1.823(4) . ?
S2 C34 1.759(7) . ?
S2 C25 1.841(4) . ?
F1 C17 1.327(5) . ?
F2 C17 1.314(6) . ?
F3 C17 1.324(5) . ?
F4 C34 1.302(8) . ?
F5 C34 1.332(7) . ?
F6 C34 1.315(6) . ?
N1 C1 1.391(6) . ?
N1 C9 1.453(6) . ?
N1 H1 0.82(5) . ?
N2 C18 1.388(6) . ?
N2 C26 1.456(6) . ?
N2 H2A 0.68(5) . ?
C1 C2 1.385(7) . ?
C1 C6 1.394(7) . ?
C2 C3 1.372(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.372(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.376(8) . ?
C4 H4 0.9300 . ?
C5 C6 1.383(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.500(6) . ?
C7 C8 1.528(6) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.537(6) . ?
C8 H8 0.9800 . ?
C9 C10 1.503(6) . ?
C9 H9 0.9800 . ?
C10 C11 1.371(6) . ?
C10 C15 1.394(7) . ?
C11 C12 1.387(7) . ?
C11 H11 0.9300 . ?
C12 C13 1.383(8) . ?
C12 C16 1.510(8) . ?
C13 C14 1.355(8) . ?
C13 H13 0.9300 . ?
C14 C15 1.380(7) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C18 C19 1.380(6) . ?
C18 C23 1.393(6) . ?
C19 C20 1.379(7) . ?
C19 H19 0.9300 . ?
C20 C21 1.361(8) . ?
C20 H20 0.9300 . ?
C21 C22 1.372(7) . ?
C21 H21 0.9300 . ?
C22 C23 1.381(6) . ?
C22 H22 0.9300 . ?
C23 C24 1.509(6) . ?
C24 C25 1.517(6) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 C26 1.523(6) . ?
C25 H25 0.9800 . ?
C26 C27 1.494(6) . ?
C26 H26 0.9800 . ?
C27 C32 1.382(6) . ?
C27 C28 1.381(6) . ?
C28 C29 1.379(7) . ?
C28 H28 0.9300 . ?
C29 C30 1.366(8) . ?
C29 H29 0.9300 . ?
C30 C31 1.376(7) . ?
C30 H30 0.9300 . ?
C31 C32 1.372(6) . ?
C31 C33 1.519(7) . ?
C32 H32 0.9300 . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 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
C17 S1 C8 99.4(2) . . ?
C34 S2 C25 99.8(3) . . ?
C1 N1 C9 118.4(4) . . ?
C1 N1 H1 116(4) . . ?
C9 N1 H1 110(4) . . ?
C18 N2 C26 119.2(4) . . ?
C18 N2 H2A 112(4) . . ?
C26 N2 H2A 113(4) . . ?
C2 C1 N1 119.9(5) . . ?
C2 C1 C6 119.2(4) . . ?
N1 C1 C6 120.8(5) . . ?
C3 C2 C1 121.0(6) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C2 C3 C4 120.1(6) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C3 C4 C5 119.4(5) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C4 C5 C6 121.5(5) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C5 C6 C1 118.8(5) . . ?
C5 C6 C7 120.8(5) . . ?
C1 C6 C7 120.4(4) . . ?
C6 C7 C8 111.5(4) . . ?
C6 C7 H7A 109.3 . . ?
C8 C7 H7A 109.3 . . ?
C6 C7 H7B 109.3 . . ?
C8 C7 H7B 109.3 . . ?
H7A C7 H7B 108.0 . . ?
C7 C8 C9 108.4(4) . . ?
C7 C8 S1 111.4(3) . . ?
C9 C8 S1 107.5(3) . . ?
C7 C8 H8 109.8 . . ?
C9 C8 H8 109.8 . . ?
S1 C8 H8 109.8 . . ?
N1 C9 C10 112.3(4) . . ?
N1 C9 C8 106.3(4) . . ?
C10 C9 C8 114.8(4) . . ?
N1 C9 H9 107.7 . . ?
C10 C9 H9 107.7 . . ?
C8 C9 H9 107.7 . . ?
C11 C10 C15 118.5(5) . . ?
C11 C10 C9 118.7(4) . . ?
C15 C10 C9 122.8(4) . . ?
C10 C11 C12 122.5(5) . . ?
C10 C11 H11 118.7 . . ?
C12 C11 H11 118.7 . . ?
C13 C12 C11 117.5(5) . . ?
C13 C12 C16 121.3(5) . . ?
C11 C12 C16 121.2(6) . . ?
C14 C13 C12 121.0(5) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C13 C14 C15 121.2(5) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
C14 C15 C10 119.3(5) . . ?
C14 C15 H15 120.4 . . ?
C10 C15 H15 120.4 . . ?
C12 C16 H16A 109.5 . . ?
C12 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C12 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
F2 C17 F3 105.8(4) . . ?
F2 C17 F1 108.0(4) . . ?
F3 C17 F1 107.0(4) . . ?
F2 C17 S1 114.2(3) . . ?
F3 C17 S1 113.9(3) . . ?
F1 C17 S1 107.6(4) . . ?
C19 C18 N2 120.4(4) . . ?
C19 C18 C23 119.3(4) . . ?
N2 C18 C23 120.3(4) . . ?
C20 C19 C18 120.9(5) . . ?
C20 C19 H19 119.5 . . ?
C18 C19 H19 119.5 . . ?
C21 C20 C19 119.9(5) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C20 C21 C22 119.5(5) . . ?
C20 C21 H21 120.2 . . ?
C22 C21 H21 120.2 . . ?
C21 C22 C23 121.8(5) . . ?
C21 C22 H22 119.1 . . ?
C23 C22 H22 119.1 . . ?
C22 C23 C18 118.4(5) . . ?
C22 C23 C24 121.1(5) . . ?
C18 C23 C24 120.5(4) . . ?
C23 C24 C25 111.2(4) . . ?
C23 C24 H24A 109.4 . . ?
C25 C24 H24A 109.4 . . ?
C23 C24 H24B 109.4 . . ?
C25 C24 H24B 109.4 . . ?
H24A C24 H24B 108.0 . . ?
C24 C25 C26 109.5(4) . . ?
C24 C25 S2 111.2(3) . . ?
C26 C25 S2 107.2(3) . . ?
C24 C25 H25 109.7 . . ?
C26 C25 H25 109.7 . . ?
S2 C25 H25 109.7 . . ?
N2 C26 C27 113.1(4) . . ?
N2 C26 C25 106.4(4) . . ?
C27 C26 C25 114.0(4) . . ?
N2 C26 H26 107.7 . . ?
C27 C26 H26 107.7 . . ?
C25 C26 H26 107.7 . . ?
C32 C27 C28 117.9(4) . . ?
C32 C27 C26 123.9(4) . . ?
C28 C27 C26 118.2(4) . . ?
C29 C28 C27 120.7(5) . . ?
C29 C28 H28 119.6 . . ?
C27 C28 H28 119.6 . . ?
C30 C29 C28 119.9(5) . . ?
C30 C29 H29 120.0 . . ?
C28 C29 H29 120.0 . . ?
C29 C30 C31 120.7(5) . . ?
C29 C30 H30 119.7 . . ?
C31 C30 H30 119.7 . . ?
C32 C31 C30 118.7(5) . . ?
C32 C31 C33 120.7(5) . . ?
C30 C31 C33 120.7(5) . . ?
C31 C32 C27 122.1(4) . . ?
C31 C32 H32 119.0 . . ?
C27 C32 H32 119.0 . . ?
C31 C33 H33A 109.5 . . ?
C31 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C31 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
F4 C34 F6 107.8(5) . . ?
F4 C34 F5 104.4(6) . . ?
F6 C34 F5 107.4(5) . . ?
F4 C34 S2 115.1(5) . . ?
F6 C34 S2 108.1(5) . . ?
F5 C34 S2 113.6(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
C9 N1 C1 C2 -162.1(5) . . . . ?
C9 N1 C1 C6 20.7(7) . . . . ?
N1 C1 C2 C3 -177.1(5) . . . . ?
C6 C1 C2 C3 0.2(8) . . . . ?
C1 C2 C3 C4 0.0(8) . . . . ?
C2 C3 C4 C5 0.0(8) . . . . ?
C3 C4 C5 C6 -0.2(8) . . . . ?
C4 C5 C6 C1 0.5(7) . . . . ?
C4 C5 C6 C7 -179.6(4) . . . . ?
C2 C1 C6 C5 -0.4(7) . . . . ?
N1 C1 C6 C5 176.8(4) . . . . ?
C2 C1 C6 C7 179.6(4) . . . . ?
N1 C1 C6 C7 -3.2(7) . . . . ?
C5 C6 C7 C8 -160.6(4) . . . . ?
C1 C6 C7 C8 19.3(6) . . . . ?
C6 C7 C8 C9 -49.9(5) . . . . ?
C6 C7 C8 S1 68.2(4) . . . . ?
C17 S1 C8 C7 89.3(4) . . . . ?
C17 S1 C8 C9 -152.0(3) . . . . ?
C1 N1 C9 C10 -177.4(4) . . . . ?
C1 N1 C9 C8 -51.2(5) . . . . ?
C7 C8 C9 N1 65.0(5) . . . . ?
S1 C8 C9 N1 -55.6(4) . . . . ?
C7 C8 C9 C10 -170.3(4) . . . . ?
S1 C8 C9 C10 69.2(4) . . . . ?
N1 C9 C10 C11 -149.2(4) . . . . ?
C8 C9 C10 C11 89.2(5) . . . . ?
N1 C9 C10 C15 31.9(6) . . . . ?
C8 C9 C10 C15 -89.6(6) . . . . ?
C15 C10 C11 C12 -0.6(7) . . . . ?
C9 C10 C11 C12 -179.5(5) . . . . ?
C10 C11 C12 C13 -0.7(7) . . . . ?
C10 C11 C12 C16 -179.2(5) . . . . ?
C11 C12 C13 C14 1.7(8) . . . . ?
C16 C12 C13 C14 -179.8(6) . . . . ?
C12 C13 C14 C15 -1.3(8) . . . . ?
C13 C14 C15 C10 0.0(8) . . . . ?
C11 C10 C15 C14 1.0(7) . . . . ?
C9 C10 C15 C14 179.8(5) . . . . ?
C8 S1 C17 F2 63.9(4) . . . . ?
C8 S1 C17 F3 -57.8(4) . . . . ?
C8 S1 C17 F1 -176.2(3) . . . . ?
C26 N2 C18 C19 -161.8(4) . . . . ?
C26 N2 C18 C23 21.0(6) . . . . ?
N2 C18 C19 C20 -178.1(4) . . . . ?
C23 C18 C19 C20 -0.9(7) . . . . ?
C18 C19 C20 C21 0.8(8) . . . . ?
C19 C20 C21 C22 0.4(8) . . . . ?
C20 C21 C22 C23 -1.6(8) . . . . ?
C21 C22 C23 C18 1.5(7) . . . . ?
C21 C22 C23 C24 -176.8(4) . . . . ?
C19 C18 C23 C22 -0.3(6) . . . . ?
N2 C18 C23 C22 177.0(4) . . . . ?
C19 C18 C23 C24 178.1(4) . . . . ?
N2 C18 C23 C24 -4.6(6) . . . . ?
C22 C23 C24 C25 -161.4(4) . . . . ?
C18 C23 C24 C25 20.3(6) . . . . ?
C23 C24 C25 C26 -49.9(5) . . . . ?
C23 C24 C25 S2 68.4(4) . . . . ?
C34 S2 C25 C24 99.0(4) . . . . ?
C34 S2 C25 C26 -141.4(4) . . . . ?
C18 N2 C26 C27 -175.9(4) . . . . ?
C18 N2 C26 C25 -50.0(5) . . . . ?
C24 C25 C26 N2 63.8(4) . . . . ?
S2 C25 C26 N2 -56.9(4) . . . . ?
C24 C25 C26 C27 -170.9(3) . . . . ?
S2 C25 C26 C27 68.4(4) . . . . ?
N2 C26 C27 C32 22.8(6) . . . . ?
C25 C26 C27 C32 -99.0(5) . . . . ?
N2 C26 C27 C28 -158.8(4) . . . . ?
C25 C26 C27 C28 79.5(5) . . . . ?
C32 C27 C28 C29 -0.6(8) . . . . ?
C26 C27 C28 C29 -179.2(5) . . . . ?
C27 C28 C29 C30 0.0(9) . . . . ?
C28 C29 C30 C31 0.9(9) . . . . ?
C29 C30 C31 C32 -1.1(8) . . . . ?
C29 C30 C31 C33 179.0(5) . . . . ?
C30 C31 C32 C27 0.5(7) . . . . ?
C33 C31 C32 C27 -179.6(4) . . . . ?
C28 C27 C32 C31 0.4(7) . . . . ?
C26 C27 C32 C31 178.8(4) . . . . ?
C25 S2 C34 F4 64.9(5) . . . . ?
C25 S2 C34 F6 -174.5(5) . . . . ?
C25 S2 C34 F5 -55.4(5) . . . . ?

_refine_diff_density_max         0.287
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.041

_shelxl_version_number           2013-4

