# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1535016'
_audit_update_record             
;
2017-02-27 deposited with the CCDC.
2017-04-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H14 F3 N O2 S'
_chemical_formula_weight         353.35

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'
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'
F F 0.0171 0.0103 '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                   5.2978(3)
_cell_length_b                   8.3344(3)
_cell_length_c                   37.1632(15)
_cell_angle_alpha                90
_cell_angle_beta                 91.094(4)
_cell_angle_gamma                90
_cell_volume                     1640.60(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(1)
_cell_measurement_reflns_used    2830
_cell_measurement_theta_min      3.6650
_cell_measurement_theta_max      28.3700

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_F_000             728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.238
_shelx_estimated_absorpt_T_min   0.965
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.89523
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   'Empirical absorption correction'

_exptl_special_details           
;
 CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      200(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'SuperNova, Sapphire3'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13051
_diffrn_reflns_av_unetI/netI     0.0628
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_limit_l_max       52
_diffrn_reflns_theta_min         3.284
_diffrn_reflns_theta_max         29.943
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.891
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.891
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.891
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4244
_reflns_number_gt                2760
_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       'CrysAlisPro, Agilent Technologies'
_computing_cell_refinement       'CrysAlisPro, Agilent Technologies'
_computing_data_reduction        'CrysAlisPro, Agilent Technologies'
_computing_structure_solution    SHELXS-2014
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0489P)²+0.8382P] 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         4244
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1031
_refine_ls_R_factor_gt           0.0615
_refine_ls_wR_factor_ref         0.1466
_refine_ls_wR_factor_gt          0.1254
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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
S S 0.77138(14) 0.12606(7) 0.59547(2) 0.03637(19) Uani 1 1 d . . . . .
O1 O 0.9831(4) 0.1063(2) 0.61974(5) 0.0476(5) Uani 1 1 d . . . . .
O2 O 0.6014(4) -0.0054(2) 0.58989(6) 0.0554(6) Uani 1 1 d . . . . .
N N 0.6062(4) 0.2867(2) 0.60726(5) 0.0317(5) Uani 1 1 d . . . . .
C1 C 0.4933(5) 0.2924(3) 0.63774(6) 0.0290(5) Uani 1 1 d . . . . .
C2 C 0.3470(5) 0.4395(3) 0.64545(6) 0.0289(5) Uani 1 1 d . . . . .
C3 C 0.1464(5) 0.4371(3) 0.66918(7) 0.0363(6) Uani 1 1 d . . . . .
H3 H 0.1081 0.3431 0.6814 0.044 Uiso 1 1 calc R U . . .
C4 C 0.0039(6) 0.5738(3) 0.67461(7) 0.0427(7) Uani 1 1 d . . . . .
H4 H -0.1302 0.5715 0.6904 0.051 Uiso 1 1 calc R U . . .
C5 C 0.0611(6) 0.7140(3) 0.65656(7) 0.0434(7) Uani 1 1 d . . . . .
H5 H -0.0345 0.8059 0.6603 0.052 Uiso 1 1 calc R U . . .
C6 C 0.2585(6) 0.7178(3) 0.63314(7) 0.0416(7) Uani 1 1 d . . . . .
H6 H 0.2957 0.8123 0.6210 0.050 Uiso 1 1 calc R U . . .
C7 C 0.4016(5) 0.5824(3) 0.62752(6) 0.0346(6) Uani 1 1 d . . . . .
H7 H 0.5354 0.5862 0.6117 0.042 Uiso 1 1 calc R U . . .
C8 C 0.5097(5) 0.1621(3) 0.66469(6) 0.0369(6) Uani 1 1 d . . . . .
H8 H 0.4848 0.0573 0.6568 0.044 Uiso 1 1 calc R U . . .
C9 C 0.5570(6) 0.1852(3) 0.69879(7) 0.0458(7) Uani 1 1 d . . . . .
H9 H 0.5690 0.2901 0.7072 0.055 Uiso 1 1 calc R U . . .
C10 C 0.5925(8) 0.0522(4) 0.72469(8) 0.0654(10) Uani 1 1 d . . . . .
C11 C 0.8817(5) 0.1876(3) 0.55334(6) 0.0311(5) Uani 1 1 d . . . . .
C12 C 1.0953(5) 0.2809(3) 0.55173(7) 0.0376(6) Uani 1 1 d . . . . .
H12 H 1.1798 0.3122 0.5727 0.045 Uiso 1 1 calc R U . . .
C13 C 1.1827(6) 0.3276(3) 0.51862(7) 0.0425(7) Uani 1 1 d . . . . .
H13 H 1.3266 0.3913 0.5176 0.051 Uiso 1 1 calc R U . . .
C14 C 1.0622(6) 0.2823(3) 0.48711(7) 0.0409(7) Uani 1 1 d . . . . .
C15 C 0.8481(6) 0.1889(4) 0.48932(7) 0.0489(7) Uani 1 1 d . . . . .
H15 H 0.7645 0.1570 0.4683 0.059 Uiso 1 1 calc R U . . .
C16 C 0.7553(6) 0.1417(3) 0.52223(7) 0.0434(7) Uani 1 1 d . . . . .
H16 H 0.6096 0.0798 0.5234 0.052 Uiso 1 1 calc R U . . .
C17 C 1.1649(7) 0.3314(4) 0.45120(7) 0.0598(9) Uani 1 1 d . . . . .
H17A H 1.3136 0.3955 0.4549 0.072 Uiso 1 1 calc R U . . .
H17B H 1.0398 0.3926 0.4382 0.072 Uiso 1 1 calc R U . . .
H17C H 1.2066 0.2373 0.4376 0.072 Uiso 1 1 calc R U . . .
F1 F 0.4533(6) 0.0655(3) 0.75298(6) 0.1085(10) Uani 1 1 d . . . . .
F2 F 0.8261(6) 0.0488(5) 0.73770(8) 0.1485(14) Uani 1 1 d . . . . .
F3 F 0.5583(7) -0.0898(3) 0.71106(6) 0.1157(11) 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
S O2 1.431(2) . ?
S O1 1.435(2) . ?
S N 1.663(2) . ?
S C11 1.758(2) . ?
N C1 1.292(3) . ?
C1 C8 1.479(3) . ?
C1 C2 1.481(3) . ?
C2 C3 1.394(3) . ?
C2 C7 1.398(3) . ?
C3 C4 1.384(4) . ?
C4 C5 1.383(4) . ?
C5 C6 1.374(4) . ?
C6 C7 1.377(3) . ?
C8 C9 1.302(3) . ?
C9 C10 1.478(4) . ?
C10 F3 1.298(4) . ?
C10 F1 1.300(4) . ?
C10 F2 1.320(5) . ?
C11 C12 1.375(4) . ?
C11 C16 1.379(4) . ?
C12 C13 1.379(3) . ?
C13 C14 1.376(4) . ?
C14 C15 1.380(4) . ?
C14 C17 1.507(4) . ?
C15 C16 1.384(4) . ?

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 S O1 119.03(13) . . ?
O2 S N 108.78(12) . . ?
O1 S N 109.60(11) . . ?
O2 S C11 108.28(12) . . ?
O1 S C11 108.92(12) . . ?
N S C11 100.67(10) . . ?
C1 N S 121.04(17) . . ?
N C1 C8 123.0(2) . . ?
N C1 C2 116.9(2) . . ?
C8 C1 C2 120.1(2) . . ?
C3 C2 C7 118.8(2) . . ?
C3 C2 C1 121.2(2) . . ?
C7 C2 C1 119.9(2) . . ?
C4 C3 C2 120.3(2) . . ?
C5 C4 C3 120.0(3) . . ?
C6 C5 C4 120.2(2) . . ?
C5 C6 C7 120.3(2) . . ?
C6 C7 C2 120.4(2) . . ?
C9 C8 C1 123.9(2) . . ?
C8 C9 C10 122.8(3) . . ?
F3 C10 F1 108.4(3) . . ?
F3 C10 F2 104.3(4) . . ?
F1 C10 F2 104.4(3) . . ?
F3 C10 C9 114.5(3) . . ?
F1 C10 C9 113.3(3) . . ?
F2 C10 C9 111.2(3) . . ?
C12 C11 C16 120.5(2) . . ?
C12 C11 S 119.44(19) . . ?
C16 C11 S 120.1(2) . . ?
C11 C12 C13 119.3(2) . . ?
C14 C13 C12 121.6(3) . . ?
C13 C14 C15 118.2(2) . . ?
C13 C14 C17 120.6(3) . . ?
C15 C14 C17 121.1(3) . . ?
C14 C15 C16 121.3(3) . . ?
C11 C16 C15 119.2(3) . . ?

_refine_diff_density_max         0.360
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.055

_shelxl_version_number           2014-1

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1535017'
_audit_update_record             
;
2017-02-27 deposited with the CCDC.
2017-04-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H22 F3 N O6 S'
_chemical_formula_weight         485.46

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'

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

_cell_length_a                   9.68066(15)
_cell_length_b                   12.6194(2)
_cell_length_c                   18.5137(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2261.71(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(1)
_cell_measurement_reflns_used    6431
_cell_measurement_theta_min      3.6630
_cell_measurement_theta_max      27.1750

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_F_000             1008
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.207
_shelx_estimated_absorpt_T_min   0.970
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.71769
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   'Empirical absorption correction'

_exptl_special_details           
;
 CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      200(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'SuperNova Sapphire3'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19354
_diffrn_reflns_av_unetI/netI     0.0423
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.229
_diffrn_reflns_theta_max         30.058
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.925
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.925
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.899
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5975
_reflns_number_gt                4950
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.733
_reflns_Friedel_fraction_max     0.866
_reflns_Friedel_fraction_full    0.999

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

_computing_data_collection       'CrysAlisPro, Agilent Technologies'
_computing_cell_refinement       'CrysAlisPro, Agilent Technologies'
_computing_data_reduction        'CrysAlisPro, Agilent Technologies'
_computing_structure_solution    SHELXS-2014
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0443P)²+0.3119P] 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 1824 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(3)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         5975
_refine_ls_number_parameters     314
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_ref         0.0991
_refine_ls_wR_factor_gt          0.0894
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.021
_refine_ls_shift/su_mean         0.003

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
S S 0.70487(7) 0.21081(5) 0.29900(4) 0.02993(16) Uani 1 1 d . . . . .
O1 O 0.6286(2) 0.22679(18) 0.36380(11) 0.0400(5) Uani 1 1 d . . . . .
O2 O 0.7418(2) 0.10626(15) 0.27663(13) 0.0417(5) Uani 1 1 d . . . . .
O3 O 0.9961(2) 0.70973(18) 0.40659(14) 0.0558(7) Uani 1 1 d . . . . .
O4 O 0.8873(2) 0.82233(15) 0.33318(12) 0.0390(5) Uani 1 1 d . . . . .
O5 O 0.91529(19) 0.63213(16) 0.22878(11) 0.0353(5) Uani 1 1 d . . . . .
O6 O 0.68526(19) 0.61330(16) 0.23127(10) 0.0330(4) Uani 1 1 d . . . . .
N N 0.8528(2) 0.27225(18) 0.30500(14) 0.0313(5) Uani 1 1 d . . . . .
C1 C 0.8792(3) 0.3700(2) 0.33949(14) 0.0266(5) Uani 1 1 d . . . . .
C2 C 1.0187(3) 0.3754(2) 0.37250(14) 0.0261(5) Uani 1 1 d . . . . .
C3 C 1.1162(3) 0.4475(2) 0.34801(16) 0.0318(6) Uani 1 1 d . . . . .
H3 H 1.0939 0.4941 0.3109 0.038 Uiso 1 1 calc R U . . .
C4 C 1.2467(3) 0.4503(2) 0.37868(17) 0.0377(7) Uani 1 1 d . . . . .
H4 H 1.3121 0.4980 0.3614 0.045 Uiso 1 1 calc R U . . .
C5 C 1.2804(3) 0.3833(2) 0.43446(17) 0.0390(7) Uani 1 1 d . . . . .
H5 H 1.3679 0.3862 0.4551 0.047 Uiso 1 1 calc R U . . .
C6 C 1.1841(3) 0.3118(3) 0.45978(16) 0.0405(7) Uani 1 1 d . . . . .
H6 H 1.2065 0.2667 0.4978 0.049 Uiso 1 1 calc R U . . .
C7 C 1.0540(3) 0.3068(2) 0.42872(15) 0.0345(6) Uani 1 1 d . . . . .
H7 H 0.9900 0.2576 0.4454 0.041 Uiso 1 1 calc R U . . .
C8 C 0.6122(3) 0.2717(2) 0.22859(14) 0.0265(5) Uani 1 1 d . . . . .
C9 C 0.6482(3) 0.2521(2) 0.15735(16) 0.0331(6) Uani 1 1 d . . . . .
H9 H 0.7221 0.2078 0.1463 0.040 Uiso 1 1 calc R U . . .
C10 C 0.5723(3) 0.2997(3) 0.10294(16) 0.0387(7) Uani 1 1 d . . . . .
H10 H 0.5953 0.2860 0.0551 0.046 Uiso 1 1 calc R U . . .
C11 C 0.4629(3) 0.3672(2) 0.11787(16) 0.0350(6) Uani 1 1 d . . . . .
C12 C 0.4287(3) 0.3846(2) 0.18997(16) 0.0336(6) Uani 1 1 d . . . . .
H12 H 0.3555 0.4294 0.2011 0.040 Uiso 1 1 calc R U . . .
C13 C 0.5012(3) 0.3368(2) 0.24515(16) 0.0304(6) Uani 1 1 d . . . . .
H13 H 0.4760 0.3482 0.2930 0.037 Uiso 1 1 calc R U . . .
C14 C 0.3840(4) 0.4206(3) 0.05821(19) 0.0529(9) Uani 1 1 d . . . . .
H14A H 0.3125 0.4640 0.0786 0.063 Uiso 1 1 calc R U . . .
H14B H 0.3433 0.3679 0.0275 0.063 Uiso 1 1 calc R U . . .
H14C H 0.4457 0.4640 0.0304 0.063 Uiso 1 1 calc R U . . .
C15 C 0.7854(3) 0.4469(2) 0.34157(15) 0.0273(5) Uani 1 1 d . . . . .
C16 C 0.8020(3) 0.5469(2) 0.38492(15) 0.0265(5) Uani 1 1 d . . . . .
C17 C 0.6940(3) 0.5489(2) 0.44404(16) 0.0371(6) Uani 1 1 d . . . . .
C18 C 0.7936(3) 0.6515(2) 0.34132(14) 0.0252(5) Uani 1 1 d . . . . .
C19 C 0.9051(3) 0.7289(2) 0.36494(15) 0.0305(6) Uani 1 1 d . . . . .
C20 C 0.9863(4) 0.9036(2) 0.35239(19) 0.0469(8) Uani 1 1 d . . . . .
H20A H 0.9649 0.9677 0.3268 0.056 Uiso 1 1 calc R U . . .
H20B H 1.0776 0.8805 0.3396 0.056 Uiso 1 1 calc R U . . .
H20C H 0.9820 0.9165 0.4034 0.056 Uiso 1 1 calc R U . . .
C21 C 0.8075(3) 0.63222(19) 0.26088(14) 0.0262(5) Uani 1 1 d . . . . .
C22 C 0.6853(3) 0.5903(3) 0.15430(15) 0.0412(7) Uani 1 1 d . . . . .
H22A H 0.5923 0.5780 0.1384 0.049 Uiso 1 1 calc R U . . .
H22B H 0.7401 0.5283 0.1453 0.049 Uiso 1 1 calc R U . . .
H22C H 0.7234 0.6494 0.1285 0.049 Uiso 1 1 calc R U . . .
F1 F 0.7115(3) 0.47031(17) 0.49125(11) 0.0639(6) Uani 1 1 d . . . . .
F2 F 0.56528(17) 0.54078(17) 0.41862(11) 0.0529(5) Uani 1 1 d . . . . .
F3 F 0.6971(2) 0.63939(15) 0.48208(10) 0.0493(5) Uani 1 1 d . . . . .
H15 H 0.696(3) 0.442(2) 0.3178(15) 0.033(8) Uiso 1 1 d . . . . .
H18 H 0.711(3) 0.685(2) 0.3520(16) 0.034(8) Uiso 1 1 d . . . . .
H16 H 0.886(3) 0.549(2) 0.4101(14) 0.020(7) Uiso 1 1 d . . . . .
H1N H 0.916(3) 0.236(2) 0.2943(16) 0.032(9) 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
S O1 1.423(2) . ?
S O2 1.428(2) . ?
S N 1.632(2) . ?
S C8 1.759(3) . ?
O3 C19 1.195(3) . ?
O4 C19 1.329(3) . ?
O4 C20 1.448(3) . ?
O5 C21 1.201(3) . ?
O6 C21 1.326(3) . ?
O6 C22 1.454(3) . ?
N C1 1.412(3) . ?
N H1N 0.79(3) . ?
C1 C15 1.330(4) . ?
C1 C2 1.484(4) . ?
C2 C3 1.387(4) . ?
C2 C7 1.397(4) . ?
C3 C4 1.386(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.374(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.381(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.385(4) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C13 1.387(4) . ?
C8 C9 1.387(4) . ?
C9 C10 1.384(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.387(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.393(4) . ?
C11 C14 1.503(4) . ?
C12 C13 1.378(4) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.504(4) . ?
C15 H15 0.98(3) . ?
C16 C17 1.514(4) . ?
C16 C18 1.549(4) . ?
C16 H16 0.94(3) . ?
C17 F1 1.332(3) . ?
C17 F2 1.336(4) . ?
C17 F3 1.342(3) . ?
C18 C21 1.515(4) . ?
C18 C19 1.520(4) . ?
C18 H18 0.92(3) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
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 S O2 120.34(13) . . ?
O1 S N 109.28(13) . . ?
O2 S N 103.84(12) . . ?
O1 S C8 107.35(12) . . ?
O2 S C8 108.44(13) . . ?
N S C8 106.89(12) . . ?
C19 O4 C20 115.7(2) . . ?
C21 O6 C22 116.2(2) . . ?
C1 N S 127.2(2) . . ?
C1 N H1N 119(2) . . ?
S N H1N 113(2) . . ?
C15 C1 N 121.8(2) . . ?
C15 C1 C2 125.1(2) . . ?
N C1 C2 113.0(2) . . ?
C3 C2 C7 118.9(2) . . ?
C3 C2 C1 121.0(2) . . ?
C7 C2 C1 120.1(2) . . ?
C2 C3 C4 120.2(3) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C5 C4 C3 120.6(3) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 119.8(3) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C5 C6 C7 120.2(3) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C6 C7 C2 120.3(3) . . ?
C6 C7 H7 119.9 . . ?
C2 C7 H7 119.9 . . ?
C13 C8 C9 120.7(3) . . ?
C13 C8 S 119.4(2) . . ?
C9 C8 S 119.9(2) . . ?
C10 C9 C8 118.8(3) . . ?
C10 C9 H9 120.6 . . ?
C8 C9 H9 120.6 . . ?
C9 C10 C11 121.8(3) . . ?
C9 C10 H10 119.1 . . ?
C11 C10 H10 119.1 . . ?
C10 C11 C12 118.0(3) . . ?
C10 C11 C14 121.1(3) . . ?
C12 C11 C14 120.8(3) . . ?
C13 C12 C11 121.3(3) . . ?
C13 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
C12 C13 C8 119.3(3) . . ?
C12 C13 H13 120.3 . . ?
C8 C13 H13 120.3 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C1 C15 C16 123.7(2) . . ?
C1 C15 H15 123.0(18) . . ?
C16 C15 H15 113.1(17) . . ?
C15 C16 C17 109.0(2) . . ?
C15 C16 C18 115.5(2) . . ?
C17 C16 C18 109.1(2) . . ?
C15 C16 H16 112.7(17) . . ?
C17 C16 H16 103.7(16) . . ?
C18 C16 H16 106.1(17) . . ?
F1 C17 F2 107.0(3) . . ?
F1 C17 F3 106.6(2) . . ?
F2 C17 F3 105.7(2) . . ?
F1 C17 C16 112.0(3) . . ?
F2 C17 C16 112.8(2) . . ?
F3 C17 C16 112.2(2) . . ?
C21 C18 C19 108.8(2) . . ?
C21 C18 C16 111.8(2) . . ?
C19 C18 C16 111.1(2) . . ?
C21 C18 H18 111.2(18) . . ?
C19 C18 H18 105.1(18) . . ?
C16 C18 H18 108.6(18) . . ?
O3 C19 O4 124.1(3) . . ?
O3 C19 C18 125.4(3) . . ?
O4 C19 C18 110.5(2) . . ?
O4 C20 H20A 109.5 . . ?
O4 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O4 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O5 C21 O6 124.8(2) . . ?
O5 C21 C18 124.3(2) . . ?
O6 C21 C18 110.9(2) . . ?
O6 C22 H22A 109.5 . . ?
O6 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O6 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

_refine_diff_density_max         0.252
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.046

_shelxl_version_number           2014-1

