# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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. 
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data_cd16161
_database_code_depnum_ccdc_archive 'CCDC 1474587'
_audit_update_record             
;
2016-04-18 deposited with the CCDC.
2018-08-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H17 Br F N O2 S'
_chemical_formula_weight         458.33

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'
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'
Br Br -0.2901 2.4595 '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                   10.0581(11)
_cell_length_b                   11.3410(12)
_cell_length_c                   17.3605(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1980.3(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2819
_cell_measurement_theta_min      4.680
_cell_measurement_theta_max      44.034

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.537
_exptl_crystal_F_000             928
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    2.208
_shelx_estimated_absorpt_T_min   0.654
_shelx_estimated_absorpt_T_max   0.762
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5510
_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            11455
_diffrn_reflns_av_unetI/netI     0.0458
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.145
_diffrn_reflns_theta_max         25.497
_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             3680
_reflns_number_gt                2971
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.747
_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          
; 
 Refined as a 2-component inversion twin. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0492P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Refined as an inversion twin. 
;
_refine_ls_abs_structure_Flack   0.478(12)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         3680
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0399
_refine_ls_wR_factor_ref         0.0894
_refine_ls_wR_factor_gt          0.0839
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_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
Br1 Br -0.39289(6) 0.62781(6) 0.10289(4) 0.0752(2) Uani 1 1 d . . . . .
S1 S 0.23526(12) 0.56345(10) 0.11685(7) 0.0450(3) Uani 1 1 d . . . . .
F1 F 0.1642(3) 0.3155(2) 0.18436(16) 0.0609(8) Uani 1 1 d . . . . .
N1 N 0.2711(4) 0.4275(3) 0.0932(2) 0.0422(9) Uani 1 1 d . . . . .
O1 O 0.2736(4) 0.5762(3) 0.19461(19) 0.0576(9) Uani 1 1 d . . . . .
O2 O 0.2911(3) 0.6367(3) 0.0594(2) 0.0585(9) Uani 1 1 d . . . . .
C1 C 0.2872(4) 0.3833(4) 0.0168(2) 0.0427(10) Uani 1 1 d . . . . .
C2 C 0.2666(5) 0.4405(5) -0.0526(3) 0.0560(13) Uani 1 1 d . . . . .
H2 H 0.2366 0.5181 -0.0544 0.067 Uiso 1 1 calc R U . . .
C3 C 0.2925(6) 0.3771(6) -0.1190(3) 0.0666(15) Uani 1 1 d . . . . .
H3 H 0.2786 0.4125 -0.1667 0.080 Uiso 1 1 calc R U . . .
C4 C 0.3381(6) 0.2637(6) -0.1163(4) 0.0715(17) Uani 1 1 d . . . . .
H4 H 0.3572 0.2237 -0.1617 0.086 Uiso 1 1 calc R U . . .
C5 C 0.3557(6) 0.2089(5) -0.0468(4) 0.0651(16) Uani 1 1 d . . . . .
H5 H 0.3852 0.1312 -0.0450 0.078 Uiso 1 1 calc R U . . .
C6 C 0.3303(5) 0.2680(4) 0.0196(3) 0.0501(12) Uani 1 1 d . . . . .
C7 C 0.3467(4) 0.2304(4) 0.1021(3) 0.0473(11) Uani 1 1 d . . . . .
C8 C 0.2840(5) 0.3334(4) 0.1493(3) 0.0472(12) Uani 1 1 d . . . . .
C9 C 0.4032(7) 0.3384(5) 0.2016(3) 0.0718(17) Uani 1 1 d . . . . .
H9A H 0.3915 0.2966 0.2499 0.086 Uiso 1 1 calc R U . . .
H9B H 0.4369 0.4174 0.2102 0.086 Uiso 1 1 calc R U . . .
C10 C 0.4803(6) 0.2686(5) 0.1405(4) 0.0693(16) Uani 1 1 d . . . . .
H10A H 0.5310 0.2033 0.1615 0.083 Uiso 1 1 calc R U . . .
H10B H 0.5356 0.3175 0.1077 0.083 Uiso 1 1 calc R U . . .
C11 C 0.2943(5) 0.1092(4) 0.1197(3) 0.0467(11) Uani 1 1 d . . . . .
C12 C 0.3710(6) 0.0209(4) 0.1526(3) 0.0559(14) Uani 1 1 d . . . . .
H12 H 0.4596 0.0358 0.1644 0.067 Uiso 1 1 calc R U . . .
C13 C 0.3180(6) -0.0885(4) 0.1679(3) 0.0603(15) Uani 1 1 d . . . . .
H13 H 0.3711 -0.1470 0.1894 0.072 Uiso 1 1 calc R U . . .
C14 C 0.1881(6) -0.1113(5) 0.1518(3) 0.0595(14) Uani 1 1 d . . . . .
H14 H 0.1517 -0.1843 0.1640 0.071 Uiso 1 1 calc R U . . .
C15 C 0.1119(6) -0.0277(5) 0.1179(3) 0.0628(14) Uani 1 1 d . . . . .
H15 H 0.0240 -0.0442 0.1052 0.075 Uiso 1 1 calc R U . . .
C16 C 0.1647(5) 0.0823(4) 0.1022(4) 0.0607(14) Uani 1 1 d . . . . .
H16 H 0.1112 0.1393 0.0793 0.073 Uiso 1 1 calc R U . . .
C17 C 0.0616(5) 0.5783(4) 0.1122(3) 0.0417(10) Uani 1 1 d . . . . .
C18 C -0.0139(5) 0.5517(5) 0.1753(3) 0.0537(13) Uani 1 1 d . . . . .
H18 H 0.0262 0.5226 0.2197 0.064 Uiso 1 1 calc R U . . .
C19 C -0.1489(5) 0.5680(5) 0.1730(3) 0.0576(14) Uani 1 1 d . . . . .
H19 H -0.2009 0.5507 0.2158 0.069 Uiso 1 1 calc R U . . .
C20 C -0.2061(5) 0.6098(4) 0.1069(3) 0.0502(11) Uani 1 1 d . . . . .
C21 C -0.1321(5) 0.6363(4) 0.0436(3) 0.0523(12) Uani 1 1 d . . . . .
H21 H -0.1727 0.6647 -0.0008 0.063 Uiso 1 1 calc R U . . .
C22 C 0.0020(5) 0.6206(5) 0.0459(3) 0.0509(12) Uani 1 1 d . . . . .
H22 H 0.0535 0.6384 0.0030 0.061 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
Br1 C20 1.891(5) . ?
S1 O1 1.411(4) . ?
S1 O2 1.415(4) . ?
S1 N1 1.635(4) . ?
S1 C17 1.756(5) . ?
F1 C8 1.365(6) . ?
N1 C1 1.428(5) . ?
N1 C8 1.450(6) . ?
C1 C6 1.378(7) . ?
C1 C2 1.383(7) . ?
C2 C3 1.385(8) . ?
C2 H2 0.9300 . ?
C3 C4 1.366(9) . ?
C3 H3 0.9300 . ?
C4 C5 1.368(8) . ?
C4 H4 0.9300 . ?
C5 C6 1.358(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.503(7) . ?
C7 C11 1.504(6) . ?
C7 C8 1.560(7) . ?
C7 C10 1.562(7) . ?
C8 C9 1.505(8) . ?
C9 C10 1.534(8) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C16 1.374(7) . ?
C11 C12 1.387(7) . ?
C12 C13 1.376(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.361(9) . ?
C13 H13 0.9300 . ?
C14 C15 1.354(8) . ?
C14 H14 0.9300 . ?
C15 C16 1.383(7) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C18 1.367(7) . ?
C17 C22 1.383(7) . ?
C18 C19 1.371(7) . ?
C18 H18 0.9300 . ?
C19 C20 1.369(7) . ?
C19 H19 0.9300 . ?
C20 C21 1.361(7) . ?
C21 C22 1.361(7) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?

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 S1 O2 120.4(2) . . ?
O1 S1 N1 106.1(2) . . ?
O2 S1 N1 106.8(2) . . ?
O1 S1 C17 107.8(2) . . ?
O2 S1 C17 107.8(2) . . ?
N1 S1 C17 107.3(2) . . ?
C1 N1 C8 110.8(4) . . ?
C1 N1 S1 126.1(3) . . ?
C8 N1 S1 123.0(3) . . ?
C6 C1 C2 121.5(5) . . ?
C6 C1 N1 109.6(4) . . ?
C2 C1 N1 128.8(4) . . ?
C1 C2 C3 117.0(5) . . ?
C1 C2 H2 121.5 . . ?
C3 C2 H2 121.5 . . ?
C4 C3 C2 121.5(6) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C3 C4 C5 120.1(5) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C6 C5 C4 120.0(5) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C1 119.8(5) . . ?
C5 C6 C7 130.4(5) . . ?
C1 C6 C7 109.7(4) . . ?
C6 C7 C11 114.5(4) . . ?
C6 C7 C8 104.1(4) . . ?
C11 C7 C8 115.8(4) . . ?
C6 C7 C10 115.1(4) . . ?
C11 C7 C10 117.9(4) . . ?
C8 C7 C10 85.2(4) . . ?
F1 C8 N1 109.3(4) . . ?
F1 C8 C9 116.1(4) . . ?
N1 C8 C9 116.7(4) . . ?
F1 C8 C7 118.7(4) . . ?
N1 C8 C7 103.6(4) . . ?
C9 C8 C7 91.3(4) . . ?
C8 C9 C10 88.1(4) . . ?
C8 C9 H9A 114.0 . . ?
C10 C9 H9A 114.0 . . ?
C8 C9 H9B 114.0 . . ?
C10 C9 H9B 114.0 . . ?
H9A C9 H9B 111.2 . . ?
C9 C10 C7 90.2(4) . . ?
C9 C10 H10A 113.6 . . ?
C7 C10 H10A 113.6 . . ?
C9 C10 H10B 113.6 . . ?
C7 C10 H10B 113.6 . . ?
H10A C10 H10B 110.9 . . ?
C16 C11 C12 117.3(5) . . ?
C16 C11 C7 119.4(4) . . ?
C12 C11 C7 123.3(5) . . ?
C13 C12 C11 121.0(5) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C14 C13 C12 120.2(5) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C15 C14 C13 120.0(5) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C16 120.0(6) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C11 C16 C15 121.4(5) . . ?
C11 C16 H16 119.3 . . ?
C15 C16 H16 119.3 . . ?
C18 C17 C22 120.1(4) . . ?
C18 C17 S1 119.6(4) . . ?
C22 C17 S1 120.2(4) . . ?
C17 C18 C19 119.8(5) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 H18 120.1 . . ?
C20 C19 C18 119.2(5) . . ?
C20 C19 H19 120.4 . . ?
C18 C19 H19 120.4 . . ?
C21 C20 C19 121.6(5) . . ?
C21 C20 Br1 119.4(4) . . ?
C19 C20 Br1 119.1(4) . . ?
C22 C21 C20 119.3(4) . . ?
C22 C21 H21 120.4 . . ?
C20 C21 H21 120.4 . . ?
C21 C22 C17 120.0(4) . . ?
C21 C22 H22 120.0 . . ?
C17 C22 H22 120.0 . . ?

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 S1 N1 C1 -160.3(4) . . . . ?
O2 S1 N1 C1 -30.7(4) . . . . ?
C17 S1 N1 C1 84.7(4) . . . . ?
O1 S1 N1 C8 23.0(4) . . . . ?
O2 S1 N1 C8 152.6(4) . . . . ?
C17 S1 N1 C8 -92.0(4) . . . . ?
C8 N1 C1 C6 -9.1(5) . . . . ?
S1 N1 C1 C6 173.8(4) . . . . ?
C8 N1 C1 C2 171.4(5) . . . . ?
S1 N1 C1 C2 -5.6(7) . . . . ?
C6 C1 C2 C3 -0.7(8) . . . . ?
N1 C1 C2 C3 178.7(5) . . . . ?
C1 C2 C3 C4 -0.8(8) . . . . ?
C2 C3 C4 C5 1.8(9) . . . . ?
C3 C4 C5 C6 -1.2(9) . . . . ?
C4 C5 C6 C1 -0.3(8) . . . . ?
C4 C5 C6 C7 -177.2(5) . . . . ?
C2 C1 C6 C5 1.2(8) . . . . ?
N1 C1 C6 C5 -178.3(5) . . . . ?
C2 C1 C6 C7 178.7(4) . . . . ?
N1 C1 C6 C7 -0.8(5) . . . . ?
C5 C6 C7 C11 -46.1(7) . . . . ?
C1 C6 C7 C11 136.8(4) . . . . ?
C5 C6 C7 C8 -173.5(5) . . . . ?
C1 C6 C7 C8 9.4(5) . . . . ?
C5 C6 C7 C10 95.3(7) . . . . ?
C1 C6 C7 C10 -81.9(5) . . . . ?
C1 N1 C8 F1 -113.1(4) . . . . ?
S1 N1 C8 F1 64.1(5) . . . . ?
C1 N1 C8 C9 112.8(5) . . . . ?
S1 N1 C8 C9 -70.0(5) . . . . ?
C1 N1 C8 C7 14.3(5) . . . . ?
S1 N1 C8 C7 -168.5(3) . . . . ?
C6 C7 C8 F1 107.3(4) . . . . ?
C11 C7 C8 F1 -19.3(6) . . . . ?
C10 C7 C8 F1 -138.0(4) . . . . ?
C6 C7 C8 N1 -14.0(5) . . . . ?
C11 C7 C8 N1 -140.6(4) . . . . ?
C10 C7 C8 N1 100.7(4) . . . . ?
C6 C7 C8 C9 -131.8(4) . . . . ?
C11 C7 C8 C9 101.6(5) . . . . ?
C10 C7 C8 C9 -17.2(4) . . . . ?
F1 C8 C9 C10 140.5(4) . . . . ?
N1 C8 C9 C10 -88.5(5) . . . . ?
C7 C8 C9 C10 17.4(4) . . . . ?
C8 C9 C10 C7 -17.4(4) . . . . ?
C6 C7 C10 C9 120.1(4) . . . . ?
C11 C7 C10 C9 -99.9(5) . . . . ?
C8 C7 C10 C9 16.8(4) . . . . ?
C6 C7 C11 C16 -54.8(6) . . . . ?
C8 C7 C11 C16 66.3(6) . . . . ?
C10 C7 C11 C16 165.0(5) . . . . ?
C6 C7 C11 C12 124.4(5) . . . . ?
C8 C7 C11 C12 -114.4(5) . . . . ?
C10 C7 C11 C12 -15.8(7) . . . . ?
C16 C11 C12 C13 -1.1(8) . . . . ?
C7 C11 C12 C13 179.7(5) . . . . ?
C11 C12 C13 C14 -0.7(8) . . . . ?
C12 C13 C14 C15 2.4(8) . . . . ?
C13 C14 C15 C16 -2.3(9) . . . . ?
C12 C11 C16 C15 1.2(8) . . . . ?
C7 C11 C16 C15 -179.5(5) . . . . ?
C14 C15 C16 C11 0.5(9) . . . . ?
O1 S1 C17 C18 -26.1(5) . . . . ?
O2 S1 C17 C18 -157.5(4) . . . . ?
N1 S1 C17 C18 87.8(4) . . . . ?
O1 S1 C17 C22 151.7(4) . . . . ?
O2 S1 C17 C22 20.3(5) . . . . ?
N1 S1 C17 C22 -94.5(4) . . . . ?
C22 C17 C18 C19 -0.5(8) . . . . ?
S1 C17 C18 C19 177.2(4) . . . . ?
C17 C18 C19 C20 0.6(9) . . . . ?
C18 C19 C20 C21 -0.4(8) . . . . ?
C18 C19 C20 Br1 178.2(4) . . . . ?
C19 C20 C21 C22 0.1(8) . . . . ?
Br1 C20 C21 C22 -178.4(4) . . . . ?
C20 C21 C22 C17 0.0(8) . . . . ?
C18 C17 C22 C21 0.2(8) . . . . ?
S1 C17 C22 C21 -177.5(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C21 H21 O2 0.93 2.50 3.228(6) 135.6 4_465
C9 H9B O1 0.97 2.45 2.998(7) 115.3 .
C2 H2 O2 0.93 2.45 2.964(6) 114.7 .
C9 H9B O1 0.97 2.45 2.998(7) 115.3 .
C2 H2 O2 0.93 2.45 2.964(6) 114.7 .
C2 H2 O2 0.93 2.45 2.964(6) 114.7 .
C9 H9B O1 0.97 2.45 2.998(7) 115.3 .
C21 H21 O2 0.93 2.50 3.228(6) 135.6 4_465
C2 H2 O2 0.93 2.45 2.964(6) 114.7 .
C9 H9B O1 0.97 2.45 2.998(7) 115.3 .
C21 H21 O2 0.93 2.50 3.228(6) 135.6 4_465
C2 H2 O2 0.93 2.45 2.964(6) 114.7 .
C9 H9B O1 0.97 2.45 2.998(7) 115.3 .
C21 H21 O2 0.93 2.50 3.228(6) 135.6 4_465
C2 H2 O2 0.93 2.45 2.964(6) 114.7 .
C9 H9B O1 0.97 2.45 2.998(7) 115.3 .
C21 H21 O2 0.93 2.50 3.228(6) 135.6 4_465

_refine_diff_density_max         0.449
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.055

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_cd16521
_database_code_depnum_ccdc_archive 'CCDC 1504263'
_audit_update_record             
;
2016-09-14 deposited with the CCDC.
2018-08-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H22 Br F3 N2 O3 S'
_chemical_formula_weight         567.41

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'
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   14.399(2)
_cell_length_b                   9.6415(16)
_cell_length_c                   17.024(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.004(4)
_cell_angle_gamma                90
_cell_volume                     2360.2(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2854
_cell_measurement_theta_min      4.792
_cell_measurement_theta_max      46.583

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.597
_exptl_crystal_F_000             1152
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.885
_shelx_estimated_absorpt_T_min   0.704
_shelx_estimated_absorpt_T_max   0.834
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5548
_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            13746
_diffrn_reflns_av_unetI/netI     0.0444
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.806
_diffrn_reflns_theta_max         25.999
_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             4644
_reflns_number_gt                3273
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker 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)+(0.0612P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4644
_refine_ls_number_parameters     318
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0680
_refine_ls_R_factor_gt           0.0428
_refine_ls_wR_factor_ref         0.1112
_refine_ls_wR_factor_gt          0.1007
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_refine_ls_shift/su_max          0.002
_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
Br1 Br 0.40060(2) -0.02148(4) 0.19702(2) 0.06385(16) Uani 1 1 d . . . . .
S1 S 0.69686(5) 0.35565(7) 0.55687(4) 0.03868(19) Uani 1 1 d . . . . .
F1 F 0.84104(14) 0.0544(3) 0.27720(11) 0.0755(6) Uani 1 1 d . . . . .
F2 F 0.82711(14) -0.1411(2) 0.33794(11) 0.0720(6) Uani 1 1 d . . . . .
F3 F 0.97903(12) 0.2987(2) 0.51738(12) 0.0717(6) Uani 1 1 d . . . . .
N1 N 0.77985(14) 0.2481(2) 0.52899(12) 0.0334(5) Uani 1 1 d . . . . .
N2 N 0.92123(15) 0.1985(3) 0.47614(14) 0.0468(6) Uani 1 1 d . . . . .
O1 O 0.78651(12) 0.20799(19) 0.39327(10) 0.0390(5) Uani 1 1 d . . . . .
O2 O 0.73677(15) 0.4901(2) 0.56239(13) 0.0539(6) Uani 1 1 d . . . . .
O3 O 0.66022(13) 0.2939(2) 0.62460(11) 0.0483(5) Uani 1 1 d . . . . .
C1 C 0.77018(16) 0.1030(3) 0.54401(15) 0.0319(6) Uani 1 1 d . . . . .
C2 C 0.77253(19) 0.0560(3) 0.62055(16) 0.0396(7) Uani 1 1 d . . . . .
H2 H 0.7739 0.1196 0.6617 0.048 Uiso 1 1 calc R U . . .
C3 C 0.7729(2) -0.0828(3) 0.63677(17) 0.0462(7) Uani 1 1 d . . . . .
H3 H 0.7733 -0.1137 0.6886 0.055 Uiso 1 1 calc R U . . .
C4 C 0.7727(2) -0.1763(3) 0.57601(18) 0.0481(8) Uani 1 1 d . . . . .
H4 H 0.7737 -0.2709 0.5866 0.058 Uiso 1 1 calc R U . . .
C5 C 0.7712(2) -0.1309(3) 0.49996(17) 0.0441(7) Uani 1 1 d . . . . .
H5 H 0.7719 -0.1956 0.4595 0.053 Uiso 1 1 calc R U . . .
C6 C 0.76859(18) 0.0094(3) 0.48130(16) 0.0339(6) Uani 1 1 d . . . . .
C7 C 0.76737(18) 0.0610(3) 0.39765(15) 0.0365(6) Uani 1 1 d . . . . .
C8 C 0.8459(2) -0.0036(4) 0.3498(2) 0.0576(9) Uani 1 1 d . . . . .
C9 C 0.9431(2) 0.0114(4) 0.3853(2) 0.0654(10) Uani 1 1 d . . . . .
H9A H 0.9863 -0.0243 0.3484 0.078 Uiso 1 1 calc R U . . .
H9B H 0.9492 -0.0451 0.4324 0.078 Uiso 1 1 calc R U . . .
C10 C 0.9703(2) 0.1588(4) 0.4064(2) 0.0644(10) Uani 1 1 d . . . . .
H10A H 1.0369 0.1650 0.4173 0.077 Uiso 1 1 calc R U . . .
H10B H 0.9532 0.2205 0.3630 0.077 Uiso 1 1 calc R U . . .
C11 C 0.83172(18) 0.2726(3) 0.45855(16) 0.0386(7) Uani 1 1 d . . . . .
C12 C 0.8448(2) 0.4214(3) 0.4338(2) 0.0571(9) Uani 1 1 d . . . . .
H12A H 0.8889 0.4252 0.3934 0.086 Uiso 1 1 calc R U . . .
H12B H 0.8675 0.4750 0.4782 0.086 Uiso 1 1 calc R U . . .
H12C H 0.7864 0.4585 0.4138 0.086 Uiso 1 1 calc R U . . .
C13 C 0.67361(19) 0.0400(3) 0.35172(16) 0.0369(6) Uani 1 1 d . . . . .
C14 C 0.65009(19) 0.1272(3) 0.28907(16) 0.0428(7) Uani 1 1 d . . . . .
H14 H 0.6895 0.2000 0.2775 0.051 Uiso 1 1 calc R U . . .
C15 C 0.5696(2) 0.1077(3) 0.24391(16) 0.0475(8) Uani 1 1 d . . . . .
H15 H 0.5550 0.1664 0.2017 0.057 Uiso 1 1 calc R U . . .
C16 C 0.5107(2) 0.0018(3) 0.26091(17) 0.0429(7) Uani 1 1 d . . . . .
C17 C 0.5315(2) -0.0849(3) 0.32315(18) 0.0510(8) Uani 1 1 d . . . . .
H17 H 0.4911 -0.1564 0.3348 0.061 Uiso 1 1 calc R U . . .
C18 C 0.6122(2) -0.0656(3) 0.36810(17) 0.0466(7) Uani 1 1 d . . . . .
H18 H 0.6260 -0.1244 0.4104 0.056 Uiso 1 1 calc R U . . .
C19 C 0.60894(18) 0.3590(3) 0.48205(15) 0.0364(6) Uani 1 1 d . . . . .
C20 C 0.5981(2) 0.4729(3) 0.43418(19) 0.0469(7) Uani 1 1 d . . . . .
H20 H 0.6372 0.5492 0.4413 0.056 Uiso 1 1 calc R U . . .
C21 C 0.5284(2) 0.4726(4) 0.37519(19) 0.0508(8) Uani 1 1 d . . . . .
H21 H 0.5216 0.5490 0.3420 0.061 Uiso 1 1 calc R U . . .
C22 C 0.46909(19) 0.3626(3) 0.36452(16) 0.0447(7) Uani 1 1 d . . . . .
C23 C 0.47996(19) 0.2504(3) 0.41435(16) 0.0448(7) Uani 1 1 d . . . . .
H23 H 0.4395 0.1756 0.4081 0.054 Uiso 1 1 calc R U . . .
C24 C 0.54917(18) 0.2466(3) 0.47305(16) 0.0393(6) Uani 1 1 d . . . . .
H24 H 0.5558 0.1700 0.5061 0.047 Uiso 1 1 calc R U . . .
C25 C 0.3955(2) 0.3641(4) 0.29865(18) 0.0608(9) Uani 1 1 d . . . . .
H25A H 0.4120 0.2998 0.2586 0.091 Uiso 1 1 calc R U . . .
H25B H 0.3907 0.4557 0.2767 0.091 Uiso 1 1 calc R U . . .
H25C H 0.3369 0.3378 0.3185 0.091 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
Br1 C16 1.888(3) . ?
S1 O2 1.419(2) . ?
S1 O3 1.423(2) . ?
S1 N1 1.670(2) . ?
S1 C19 1.748(3) . ?
F1 C8 1.356(4) . ?
F2 C8 1.366(4) . ?
F3 N2 1.435(3) . ?
N1 C1 1.430(3) . ?
N1 C11 1.465(3) . ?
N2 C10 1.464(4) . ?
N2 C11 1.490(4) . ?
O1 C11 1.404(3) . ?
O1 C7 1.446(3) . ?
C1 C2 1.378(4) . ?
C1 C6 1.397(4) . ?
C2 C3 1.367(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.372(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.366(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.389(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.508(4) . ?
C7 C13 1.538(4) . ?
C7 C8 1.558(4) . ?
C8 C9 1.502(5) . ?
C9 C10 1.512(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.510(4) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C18 1.386(4) . ?
C13 C14 1.386(4) . ?
C14 C15 1.370(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.368(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.370(4) . ?
C17 C18 1.371(4) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C20 1.371(4) . ?
C19 C24 1.388(4) . ?
C20 C21 1.383(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.368(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.378(4) . ?
C22 C25 1.502(4) . ?
C23 C24 1.374(4) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 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
O2 S1 O3 119.64(13) . . ?
O2 S1 N1 107.04(12) . . ?
O3 S1 N1 105.75(11) . . ?
O2 S1 C19 107.86(13) . . ?
O3 S1 C19 108.22(13) . . ?
N1 S1 C19 107.81(11) . . ?
C1 N1 C11 111.3(2) . . ?
C1 N1 S1 118.62(17) . . ?
C11 N1 S1 122.37(18) . . ?
F3 N2 C10 106.3(2) . . ?
F3 N2 C11 104.4(2) . . ?
C10 N2 C11 114.3(2) . . ?
C11 O1 C7 118.4(2) . . ?
C2 C1 C6 120.6(3) . . ?
C2 C1 N1 119.5(2) . . ?
C6 C1 N1 119.5(2) . . ?
C3 C2 C1 120.8(3) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C2 C3 C4 119.4(3) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C5 C4 C3 120.2(3) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 121.9(3) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C5 C6 C1 117.1(2) . . ?
C5 C6 C7 122.4(2) . . ?
C1 C6 C7 120.5(2) . . ?
O1 C7 C6 112.3(2) . . ?
O1 C7 C13 105.5(2) . . ?
C6 C7 C13 113.8(2) . . ?
O1 C7 C8 102.7(2) . . ?
C6 C7 C8 112.9(2) . . ?
C13 C7 C8 108.9(2) . . ?
F1 C8 F2 105.4(3) . . ?
F1 C8 C9 109.3(3) . . ?
F2 C8 C9 109.1(3) . . ?
F1 C8 C7 107.9(3) . . ?
F2 C8 C7 108.8(3) . . ?
C9 C8 C7 116.0(3) . . ?
C8 C9 C10 114.2(3) . . ?
C8 C9 H9A 108.7 . . ?
C10 C9 H9A 108.7 . . ?
C8 C9 H9B 108.7 . . ?
C10 C9 H9B 108.7 . . ?
H9A C9 H9B 107.6 . . ?
N2 C10 C9 108.0(3) . . ?
N2 C10 H10A 110.1 . . ?
C9 C10 H10A 110.1 . . ?
N2 C10 H10B 110.1 . . ?
C9 C10 H10B 110.1 . . ?
H10A C10 H10B 108.4 . . ?
O1 C11 N1 109.9(2) . . ?
O1 C11 N2 107.9(2) . . ?
N1 C11 N2 103.3(2) . . ?
O1 C11 C12 105.1(2) . . ?
N1 C11 C12 117.3(2) . . ?
N2 C11 C12 113.1(2) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C18 C13 C14 117.9(3) . . ?
C18 C13 C7 123.2(3) . . ?
C14 C13 C7 118.9(2) . . ?
C15 C14 C13 120.9(3) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C16 C15 C14 120.0(3) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C17 120.4(3) . . ?
C15 C16 Br1 118.6(2) . . ?
C17 C16 Br1 121.1(2) . . ?
C16 C17 C18 119.6(3) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 H17 120.2 . . ?
C17 C18 C13 121.3(3) . . ?
C17 C18 H18 119.4 . . ?
C13 C18 H18 119.4 . . ?
C20 C19 C24 120.6(3) . . ?
C20 C19 S1 120.2(2) . . ?
C24 C19 S1 119.2(2) . . ?
C19 C20 C21 119.0(3) . . ?
C19 C20 H20 120.5 . . ?
C21 C20 H20 120.5 . . ?
C22 C21 C20 121.5(3) . . ?
C22 C21 H21 119.2 . . ?
C20 C21 H21 119.2 . . ?
C21 C22 C23 118.5(3) . . ?
C21 C22 C25 120.2(3) . . ?
C23 C22 C25 121.3(3) . . ?
C24 C23 C22 121.6(3) . . ?
C24 C23 H23 119.2 . . ?
C22 C23 H23 119.2 . . ?
C23 C24 C19 118.8(3) . . ?
C23 C24 H24 120.6 . . ?
C19 C24 H24 120.6 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 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
O2 S1 N1 C1 159.13(19) . . . . ?
O3 S1 N1 C1 30.5(2) . . . . ?
C19 S1 N1 C1 -85.1(2) . . . . ?
O2 S1 N1 C11 -54.2(2) . . . . ?
O3 S1 N1 C11 177.2(2) . . . . ?
C19 S1 N1 C11 61.6(2) . . . . ?
C11 N1 C1 C2 144.5(2) . . . . ?
S1 N1 C1 C2 -65.4(3) . . . . ?
C11 N1 C1 C6 -28.6(3) . . . . ?
S1 N1 C1 C6 121.5(2) . . . . ?
C6 C1 C2 C3 -0.3(4) . . . . ?
N1 C1 C2 C3 -173.4(2) . . . . ?
C1 C2 C3 C4 1.3(4) . . . . ?
C2 C3 C4 C5 -0.7(4) . . . . ?
C3 C4 C5 C6 -0.8(4) . . . . ?
C4 C5 C6 C1 1.7(4) . . . . ?
C4 C5 C6 C7 179.7(3) . . . . ?
C2 C1 C6 C5 -1.1(4) . . . . ?
N1 C1 C6 C5 171.9(2) . . . . ?
C2 C1 C6 C7 -179.1(2) . . . . ?
N1 C1 C6 C7 -6.1(4) . . . . ?
C11 O1 C7 C6 20.3(3) . . . . ?
C11 O1 C7 C13 144.7(2) . . . . ?
C11 O1 C7 C8 -101.2(3) . . . . ?
C5 C6 C7 O1 -166.4(2) . . . . ?
C1 C6 C7 O1 11.5(3) . . . . ?
C5 C6 C7 C13 73.8(3) . . . . ?
C1 C6 C7 C13 -108.3(3) . . . . ?
C5 C6 C7 C8 -50.9(4) . . . . ?
C1 C6 C7 C8 127.0(3) . . . . ?
O1 C7 C8 F1 -56.1(3) . . . . ?
C6 C7 C8 F1 -177.2(3) . . . . ?
C13 C7 C8 F1 55.4(3) . . . . ?
O1 C7 C8 F2 -169.9(2) . . . . ?
C6 C7 C8 F2 69.0(3) . . . . ?
C13 C7 C8 F2 -58.4(3) . . . . ?
O1 C7 C8 C9 66.8(3) . . . . ?
C6 C7 C8 C9 -54.4(4) . . . . ?
C13 C7 C8 C9 178.3(3) . . . . ?
F1 C8 C9 C10 69.2(4) . . . . ?
F2 C8 C9 C10 -176.1(3) . . . . ?
C7 C8 C9 C10 -53.0(4) . . . . ?
F3 N2 C10 C9 151.0(3) . . . . ?
C11 N2 C10 C9 -94.4(3) . . . . ?
C8 C9 C10 N2 73.0(4) . . . . ?
C7 O1 C11 N1 -55.4(3) . . . . ?
C7 O1 C11 N2 56.6(3) . . . . ?
C7 O1 C11 C12 177.5(2) . . . . ?
C1 N1 C11 O1 58.2(3) . . . . ?
S1 N1 C11 O1 -90.6(2) . . . . ?
C1 N1 C11 N2 -56.7(3) . . . . ?
S1 N1 C11 N2 154.44(18) . . . . ?
C1 N1 C11 C12 178.1(2) . . . . ?
S1 N1 C11 C12 29.2(3) . . . . ?
F3 N2 C11 O1 156.1(2) . . . . ?
C10 N2 C11 O1 40.4(3) . . . . ?
F3 N2 C11 N1 -87.5(2) . . . . ?
C10 N2 C11 N1 156.8(2) . . . . ?
F3 N2 C11 C12 40.4(3) . . . . ?
C10 N2 C11 C12 -75.3(3) . . . . ?
O1 C7 C13 C18 -151.5(3) . . . . ?
C6 C7 C13 C18 -27.9(4) . . . . ?
C8 C7 C13 C18 98.9(3) . . . . ?
O1 C7 C13 C14 30.8(3) . . . . ?
C6 C7 C13 C14 154.4(2) . . . . ?
C8 C7 C13 C14 -78.8(3) . . . . ?
C18 C13 C14 C15 -1.3(4) . . . . ?
C7 C13 C14 C15 176.5(3) . . . . ?
C13 C14 C15 C16 0.7(4) . . . . ?
C14 C15 C16 C17 0.2(4) . . . . ?
C14 C15 C16 Br1 -179.9(2) . . . . ?
C15 C16 C17 C18 -0.5(5) . . . . ?
Br1 C16 C17 C18 179.7(2) . . . . ?
C16 C17 C18 C13 -0.2(5) . . . . ?
C14 C13 C18 C17 1.1(4) . . . . ?
C7 C13 C18 C17 -176.6(3) . . . . ?
O2 S1 C19 C20 8.7(3) . . . . ?
O3 S1 C19 C20 139.4(2) . . . . ?
N1 S1 C19 C20 -106.6(2) . . . . ?
O2 S1 C19 C24 -169.8(2) . . . . ?
O3 S1 C19 C24 -39.1(2) . . . . ?
N1 S1 C19 C24 74.9(2) . . . . ?
C24 C19 C20 C21 -1.8(4) . . . . ?
S1 C19 C20 C21 179.7(2) . . . . ?
C19 C20 C21 C22 1.2(5) . . . . ?
C20 C21 C22 C23 0.2(4) . . . . ?
C20 C21 C22 C25 -178.5(3) . . . . ?
C21 C22 C23 C24 -0.9(4) . . . . ?
C25 C22 C23 C24 177.8(3) . . . . ?
C22 C23 C24 C19 0.2(4) . . . . ?
C20 C19 C24 C23 1.1(4) . . . . ?
S1 C19 C24 C23 179.7(2) . . . . ?

_refine_diff_density_max         0.650
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.068

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_d8v18328
_database_code_depnum_ccdc_archive 'CCDC 1838252'
_audit_update_record             
;
2018-04-19 deposited with the CCDC.
2018-08-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H19 F2 N O2 S'
_chemical_formula_weight         399.44

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   14.943(3)
_cell_length_b                   11.511(2)
_cell_length_c                   11.392(2)
_cell_angle_alpha                90
_cell_angle_beta                 98.266(6)
_cell_angle_gamma                90
_cell_volume                     1939.0(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7532
_cell_measurement_theta_min      4.484
_cell_measurement_theta_max      51.799

_exptl_crystal_description       prismatic
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_F_000             832
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.203
_shelx_estimated_absorpt_T_min   0.961
_shelx_estimated_absorpt_T_max   0.974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5943
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22631
_diffrn_reflns_av_unetI/netI     0.0378
_diffrn_reflns_av_R_equivalents  0.0619
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.529
_diffrn_reflns_theta_max         25.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             3552
_reflns_number_gt                2463
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_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)+(0.0715P)²+1.6485P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0056(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3552
_refine_ls_number_parameters     256
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0986
_refine_ls_R_factor_gt           0.0651
_refine_ls_wR_factor_ref         0.1777
_refine_ls_wR_factor_gt          0.1539
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.091
_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
S1 S 0.77248(6) 0.45748(8) 0.38068(8) 0.0530(3) Uani 1 1 d . . . . .
F1 F 0.61176(18) 0.4478(2) 0.5283(2) 0.0871(8) Uani 1 1 d . . . . .
F2 F 0.90569(14) 0.2537(2) 0.4738(2) 0.0728(7) Uani 1 1 d . . . . .
O1 O 0.68750(17) 0.5016(2) 0.3285(2) 0.0659(7) Uani 1 1 d . . . . .
O2 O 0.84541(18) 0.4506(2) 0.3119(2) 0.0664(7) Uani 1 1 d . . . . .
N1 N 0.75938(19) 0.3228(2) 0.4240(2) 0.0505(7) Uani 1 1 d . . . . .
C1 C 0.5581(2) 0.2682(3) 0.5853(3) 0.0517(8) Uani 1 1 d . . . . .
C2 C 0.4891(2) 0.3231(3) 0.6372(4) 0.0633(10) Uani 1 1 d . . . . .
H2 H 0.4814 0.4030 0.6301 0.076 Uiso 1 1 calc R U . . .
C3 C 0.4334(3) 0.2595(4) 0.6980(4) 0.0759(12) Uani 1 1 d . . . . .
H3 H 0.3889 0.2968 0.7333 0.091 Uiso 1 1 calc R U . . .
C4 C 0.4429(3) 0.1401(4) 0.7074(4) 0.0783(12) Uani 1 1 d . . . . .
H4 H 0.4044 0.0977 0.7485 0.094 Uiso 1 1 calc R U . . .
C5 C 0.5079(3) 0.0840(4) 0.6570(4) 0.0691(11) Uani 1 1 d . . . . .
H5 H 0.5129 0.0036 0.6630 0.083 Uiso 1 1 calc R U . . .
C6 C 0.5678(2) 0.1471(3) 0.5956(3) 0.0545(9) Uani 1 1 d . . . . .
C7 C 0.6393(3) 0.0915(3) 0.5463(3) 0.0581(9) Uani 1 1 d . . . . .
H7 H 0.6466 0.0114 0.5526 0.070 Uiso 1 1 calc R U . . .
C8 C 0.6964(2) 0.1556(3) 0.4902(3) 0.0498(8) Uani 1 1 d . . . . .
C9 C 0.6878(2) 0.2774(3) 0.4817(3) 0.0484(8) Uani 1 1 d . . . . .
C10 C 0.6201(2) 0.3313(3) 0.5269(3) 0.0516(8) Uani 1 1 d . . . . .
C11 C 0.7752(2) 0.1176(3) 0.4318(3) 0.0547(9) Uani 1 1 d . . . . .
C12 C 0.7547(3) 0.1010(3) 0.2939(3) 0.0678(11) Uani 1 1 d . . . . .
H12A H 0.7696 0.0242 0.2674 0.081 Uiso 1 1 calc R U . . .
H12B H 0.6936 0.1228 0.2602 0.081 Uiso 1 1 calc R U . . .
C13 C 0.8261(3) 0.1939(4) 0.2779(3) 0.0720(12) Uani 1 1 d . . . . .
H13A H 0.8839 0.1623 0.2642 0.086 Uiso 1 1 calc R U . . .
H13B H 0.8051 0.2531 0.2198 0.086 Uiso 1 1 calc R U . . .
C14 C 0.8231(2) 0.2306(3) 0.4055(3) 0.0554(9) Uani 1 1 d . . . . .
C15 C 0.8350(3) 0.0238(4) 0.4945(4) 0.0768(12) Uani 1 1 d . . . . .
H15A H 0.8530 0.0456 0.5758 0.115 Uiso 1 1 calc R U . . .
H15B H 0.8877 0.0144 0.4562 0.115 Uiso 1 1 calc R U . . .
H15C H 0.8022 -0.0481 0.4912 0.115 Uiso 1 1 calc R U . . .
C16 C 0.8101(2) 0.5392(3) 0.5096(3) 0.0479(8) Uani 1 1 d . . . . .
C17 C 0.8956(2) 0.5181(3) 0.5707(3) 0.0551(9) Uani 1 1 d . . . . .
H17 H 0.9306 0.4575 0.5481 0.066 Uiso 1 1 calc R U . . .
C18 C 0.9282(2) 0.5886(3) 0.6655(4) 0.0616(10) Uani 1 1 d . . . . .
H18 H 0.9854 0.5744 0.7069 0.074 Uiso 1 1 calc R U . . .
C19 C 0.8779(3) 0.6794(3) 0.7003(3) 0.0606(10) Uani 1 1 d . . . . .
C20 C 0.7927(3) 0.6992(3) 0.6380(4) 0.0635(10) Uani 1 1 d . . . . .
H20 H 0.7581 0.7604 0.6601 0.076 Uiso 1 1 calc R U . . .
C21 C 0.7579(2) 0.6291(3) 0.5427(3) 0.0562(9) Uani 1 1 d . . . . .
H21 H 0.7004 0.6426 0.5019 0.067 Uiso 1 1 calc R U . . .
C22 C 0.9141(3) 0.7548(4) 0.8044(4) 0.0918(15) Uani 1 1 d . . . . .
H22A H 0.9738 0.7294 0.8365 0.138 Uiso 1 1 calc R U . . .
H22B H 0.8752 0.7490 0.8643 0.138 Uiso 1 1 calc R U . . .
H22C H 0.9164 0.8341 0.7789 0.138 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 O1 1.417(3) . ?
S1 O2 1.433(3) . ?
S1 N1 1.647(3) . ?
S1 C16 1.767(3) . ?
F1 C10 1.347(4) . ?
F2 C14 1.386(4) . ?
N1 C9 1.432(4) . ?
N1 C14 1.462(4) . ?
C1 C6 1.405(5) . ?
C1 C2 1.409(5) . ?
C1 C10 1.417(5) . ?
C2 C3 1.369(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.385(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.359(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.413(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.428(5) . ?
C7 C8 1.356(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.409(5) . ?
C8 C11 1.498(5) . ?
C9 C10 1.351(5) . ?
C11 C15 1.514(5) . ?
C11 C14 1.535(5) . ?
C11 C12 1.568(5) . ?
C12 C13 1.540(6) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.520(5) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C21 1.381(5) . ?
C16 C17 1.386(5) . ?
C17 C18 1.382(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.379(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.384(5) . ?
C19 C22 1.506(5) . ?
C20 C21 1.391(5) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 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 S1 O2 119.81(16) . . ?
O1 S1 N1 108.99(16) . . ?
O2 S1 N1 104.13(15) . . ?
O1 S1 C16 108.45(16) . . ?
O2 S1 C16 107.92(16) . . ?
N1 S1 C16 106.82(15) . . ?
C9 N1 C14 110.2(3) . . ?
C9 N1 S1 127.6(2) . . ?
C14 N1 S1 122.2(2) . . ?
C6 C1 C2 118.9(3) . . ?
C6 C1 C10 118.8(3) . . ?
C2 C1 C10 122.3(3) . . ?
C3 C2 C1 120.5(4) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 120.4(4) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C5 C4 C3 120.7(4) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 120.5(4) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 119.0(3) . . ?
C1 C6 C7 119.1(3) . . ?
C5 C6 C7 121.8(3) . . ?
C8 C7 C6 119.9(3) . . ?
C8 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
C7 C8 C9 121.1(3) . . ?
C7 C8 C11 129.6(3) . . ?
C9 C8 C11 109.2(3) . . ?
C10 C9 C8 119.7(3) . . ?
C10 C9 N1 131.1(3) . . ?
C8 C9 N1 109.2(3) . . ?
F1 C10 C9 122.5(3) . . ?
F1 C10 C1 115.9(3) . . ?
C9 C10 C1 121.3(3) . . ?
C8 C11 C15 116.5(3) . . ?
C8 C11 C14 105.0(3) . . ?
C15 C11 C14 115.8(3) . . ?
C8 C11 C12 115.3(3) . . ?
C15 C11 C12 113.8(3) . . ?
C14 C11 C12 86.4(3) . . ?
C13 C12 C11 89.7(3) . . ?
C13 C12 H12A 113.7 . . ?
C11 C12 H12A 113.7 . . ?
C13 C12 H12B 113.7 . . ?
C11 C12 H12B 113.7 . . ?
H12A C12 H12B 110.9 . . ?
C14 C13 C12 87.9(3) . . ?
C14 C13 H13A 114.0 . . ?
C12 C13 H13A 114.0 . . ?
C14 C13 H13B 114.0 . . ?
C12 C13 H13B 114.0 . . ?
H13A C13 H13B 111.2 . . ?
F2 C14 N1 109.0(3) . . ?
F2 C14 C13 116.4(3) . . ?
N1 C14 C13 116.7(3) . . ?
F2 C14 C11 117.1(3) . . ?
N1 C14 C11 104.8(3) . . ?
C13 C14 C11 91.7(3) . . ?
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 . . ?
C21 C16 C17 120.7(3) . . ?
C21 C16 S1 120.1(3) . . ?
C17 C16 S1 119.0(3) . . ?
C18 C17 C16 119.0(3) . . ?
C18 C17 H17 120.5 . . ?
C16 C17 H17 120.5 . . ?
C19 C18 C17 121.6(3) . . ?
C19 C18 H18 119.2 . . ?
C17 C18 H18 119.2 . . ?
C18 C19 C20 118.4(3) . . ?
C18 C19 C22 121.0(4) . . ?
C20 C19 C22 120.6(4) . . ?
C19 C20 C21 121.2(3) . . ?
C19 C20 H20 119.4 . . ?
C21 C20 H20 119.4 . . ?
C16 C21 C20 119.0(3) . . ?
C16 C21 H21 120.5 . . ?
C20 C21 H21 120.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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
O1 S1 N1 C9 -41.8(3) . . . . ?
O2 S1 N1 C9 -170.8(3) . . . . ?
C16 S1 N1 C9 75.2(3) . . . . ?
O1 S1 N1 C14 137.5(3) . . . . ?
O2 S1 N1 C14 8.6(3) . . . . ?
C16 S1 N1 C14 -105.5(3) . . . . ?
C6 C1 C2 C3 0.9(6) . . . . ?
C10 C1 C2 C3 -176.7(4) . . . . ?
C1 C2 C3 C4 -1.3(7) . . . . ?
C2 C3 C4 C5 0.4(7) . . . . ?
C3 C4 C5 C6 0.9(7) . . . . ?
C2 C1 C6 C5 0.4(5) . . . . ?
C10 C1 C6 C5 178.1(3) . . . . ?
C2 C1 C6 C7 -178.2(3) . . . . ?
C10 C1 C6 C7 -0.5(5) . . . . ?
C4 C5 C6 C1 -1.3(6) . . . . ?
C4 C5 C6 C7 177.2(4) . . . . ?
C1 C6 C7 C8 -0.2(5) . . . . ?
C5 C6 C7 C8 -178.7(3) . . . . ?
C6 C7 C8 C9 1.4(5) . . . . ?
C6 C7 C8 C11 -179.8(3) . . . . ?
C7 C8 C9 C10 -2.0(5) . . . . ?
C11 C8 C9 C10 179.0(3) . . . . ?
C7 C8 C9 N1 177.0(3) . . . . ?
C11 C8 C9 N1 -2.1(4) . . . . ?
C14 N1 C9 C10 172.3(3) . . . . ?
S1 N1 C9 C10 -8.3(5) . . . . ?
C14 N1 C9 C8 -6.5(4) . . . . ?
S1 N1 C9 C8 172.9(2) . . . . ?
C8 C9 C10 F1 175.7(3) . . . . ?
N1 C9 C10 F1 -3.0(6) . . . . ?
C8 C9 C10 C1 1.3(5) . . . . ?
N1 C9 C10 C1 -177.3(3) . . . . ?
C6 C1 C10 F1 -174.8(3) . . . . ?
C2 C1 C10 F1 2.8(5) . . . . ?
C6 C1 C10 C9 -0.1(5) . . . . ?
C2 C1 C10 C9 177.5(3) . . . . ?
C7 C8 C11 C15 -40.1(5) . . . . ?
C9 C8 C11 C15 138.9(3) . . . . ?
C7 C8 C11 C14 -169.7(3) . . . . ?
C9 C8 C11 C14 9.3(4) . . . . ?
C7 C8 C11 C12 97.2(4) . . . . ?
C9 C8 C11 C12 -83.9(4) . . . . ?
C8 C11 C12 C13 120.1(3) . . . . ?
C15 C11 C12 C13 -101.4(4) . . . . ?
C14 C11 C12 C13 15.3(3) . . . . ?
C11 C12 C13 C14 -15.4(3) . . . . ?
C9 N1 C14 F2 -114.1(3) . . . . ?
S1 N1 C14 F2 66.4(4) . . . . ?
C9 N1 C14 C13 111.6(4) . . . . ?
S1 N1 C14 C13 -67.9(4) . . . . ?
C9 N1 C14 C11 12.0(4) . . . . ?
S1 N1 C14 C11 -167.5(2) . . . . ?
C12 C13 C14 F2 137.4(3) . . . . ?
C12 C13 C14 N1 -91.7(4) . . . . ?
C12 C13 C14 C11 15.8(3) . . . . ?
C8 C11 C14 F2 108.3(3) . . . . ?
C15 C11 C14 F2 -21.8(5) . . . . ?
C12 C11 C14 F2 -136.5(3) . . . . ?
C8 C11 C14 N1 -12.6(3) . . . . ?
C15 C11 C14 N1 -142.6(3) . . . . ?
C12 C11 C14 N1 102.7(3) . . . . ?
C8 C11 C14 C13 -130.8(3) . . . . ?
C15 C11 C14 C13 99.2(4) . . . . ?
C12 C11 C14 C13 -15.5(3) . . . . ?
O1 S1 C16 C21 -0.2(3) . . . . ?
O2 S1 C16 C21 131.0(3) . . . . ?
N1 S1 C16 C21 -117.5(3) . . . . ?
O1 S1 C16 C17 -174.7(3) . . . . ?
O2 S1 C16 C17 -43.5(3) . . . . ?
N1 S1 C16 C17 68.0(3) . . . . ?
C21 C16 C17 C18 0.0(5) . . . . ?
S1 C16 C17 C18 174.5(3) . . . . ?
C16 C17 C18 C19 -0.4(6) . . . . ?
C17 C18 C19 C20 0.2(6) . . . . ?
C17 C18 C19 C22 179.6(4) . . . . ?
C18 C19 C20 C21 0.3(6) . . . . ?
C22 C19 C20 C21 -179.1(4) . . . . ?
C17 C16 C21 C20 0.4(5) . . . . ?
S1 C16 C21 C20 -173.9(3) . . . . ?
C19 C20 C21 C16 -0.6(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C17 H17 F2 0.93 2.50 3.249(4) 137.2 .

_refine_diff_density_max         0.257
_refine_diff_density_min         -0.402
_refine_diff_density_rms         0.055

_shelxl_version_number           2013-4

