# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1941435'
loop_
_audit_author_name
_audit_author_address
'shuanglin qin'
;Tianjin University
China
;
_audit_update_record             
;
2019-07-18 deposited with the CCDC.	2020-06-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H17 F6 N O S'
_chemical_formula_weight         373.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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                   7.34650(10)
_cell_length_b                   13.64660(10)
_cell_length_c                   17.5192(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1756.38(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    42911
_cell_measurement_theta_min      4.1350
_cell_measurement_theta_max      73.7420

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    none
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_F_000             768
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    2.231
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.75
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_number            64477
_diffrn_reflns_av_unetI/netI     0.0194
_diffrn_reflns_av_R_equivalents  0.0770
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         4.106
_diffrn_reflns_theta_max         74.246
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3543
_reflns_number_gt                3475
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.733
_reflns_Friedel_fraction_max     0.990
_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       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    WINGX
_computing_publication_material  WINGX
_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)+(0.0782P)²+0.5478P] 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 
;
 Flack x determined using 1437 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.007(6)
_chemical_absolute_configuration UNK
_refine_ls_number_reflns         3543
_refine_ls_number_parameters     220
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0421
_refine_ls_wR_factor_ref         0.1177
_refine_ls_wR_factor_gt          0.1173
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_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 0.53400(11) 0.62326(5) 0.56818(4) 0.0395(2) Uani 1 1 d . . . . .
F4 F 0.5554(3) 0.99775(16) 0.62301(14) 0.0637(6) Uani 1 1 d . . . . .
F5 F 0.2918(3) 0.98307(15) 0.67241(13) 0.0568(5) Uani 1 1 d . . . . .
O1 O 0.4763(4) 0.67700(16) 0.49840(12) 0.0469(5) Uani 1 1 d . . . . .
F6 F 0.3185(4) 1.01471(16) 0.55295(14) 0.0749(7) Uani 1 1 d . . . . .
N1 N 0.5466(4) 0.69635(18) 0.64575(14) 0.0389(5) Uani 1 1 d . . . . .
F3 F 1.2396(5) 0.8690(2) 0.92029(16) 0.0948(10) Uani 1 1 d . . . . .
F1 F 1.0882(5) 0.7603(3) 0.97343(15) 0.1053(12) Uani 1 1 d . . . . .
C12 C 0.3891(5) 0.9618(2) 0.60939(18) 0.0450(7) Uani 1 1 d . . . . .
C8 C 0.6828(4) 0.7749(2) 0.64841(17) 0.0389(6) Uani 1 1 d . . . . .
H8 H 0.7399 0.7915 0.5995 0.047 Uiso 1 1 calc R U . . .
C9 C 0.4844(4) 0.7976(2) 0.65457(16) 0.0394(6) Uani 1 1 d . . . . .
H9 H 0.4438 0.8143 0.7062 0.047 Uiso 1 1 calc R U . . .
C7 C 0.8055(4) 0.7767(2) 0.71611(17) 0.0380(6) Uani 1 1 d . . . . .
C6 C 0.9510(5) 0.8416(2) 0.71765(18) 0.0434(6) Uani 1 1 d . . . . .
H6 H 0.9714 0.8831 0.6764 0.052 Uiso 1 1 calc R U . . .
C2 C 1.0362(5) 0.7829(2) 0.84177(18) 0.0470(7) Uani 1 1 d . . . . .
C1 C 1.1663(6) 0.7834(3) 0.9074(2) 0.0615(10) Uani 1 1 d . . . . .
C11 C 0.3895(5) 0.8546(2) 0.59160(17) 0.0415(7) Uani 1 1 d . . . . .
H11A H 0.4516 0.8435 0.5435 0.050 Uiso 1 1 calc R U . . .
H11B H 0.2652 0.8316 0.5864 0.050 Uiso 1 1 calc R U . . .
F2 F 1.2966(7) 0.7220(4) 0.8982(3) 0.172(3) Uani 1 1 d . . . . .
C3 C 1.0660(4) 0.8447(2) 0.78045(19) 0.0455(7) Uani 1 1 d . . . . .
H3 H 1.1631 0.8884 0.7813 0.055 Uiso 1 1 calc R U . . .
C16 C 0.3082(6) 0.4779(3) 0.5347(2) 0.0602(9) Uani 1 1 d . . . . .
H16A H 0.2905 0.5131 0.4878 0.090 Uiso 1 1 calc R U . . .
H16B H 0.2031 0.4382 0.5449 0.090 Uiso 1 1 calc R U . . .
H16C H 0.4136 0.4367 0.5303 0.090 Uiso 1 1 calc R U . . .
C13 C 0.3358(5) 0.5506(2) 0.6000(2) 0.0459(7) Uani 1 1 d . . . . .
C15 C 0.1711(5) 0.6161(3) 0.6111(2) 0.0567(9) Uani 1 1 d . . . . .
H15A H 0.1848 0.6529 0.6574 0.085 Uiso 1 1 calc R U . . .
H15B H 0.0634 0.5764 0.6142 0.085 Uiso 1 1 calc R U . . .
H15C H 0.1609 0.6602 0.5686 0.085 Uiso 1 1 calc R U . . .
C14 C 0.3901(6) 0.4977(3) 0.6729(2) 0.0571(9) Uani 1 1 d . . . . .
H14A H 0.5041 0.4648 0.6653 0.086 Uiso 1 1 calc R U . . .
H14B H 0.2982 0.4505 0.6859 0.086 Uiso 1 1 calc R U . . .
H14C H 0.4021 0.5443 0.7136 0.086 Uiso 1 1 calc R U . . .
C4 C 0.8887(7) 0.7203(3) 0.8410(2) 0.0640(11) Uani 1 1 d . . . . .
H4 H 0.8660 0.6804 0.8830 0.077 Uiso 1 1 calc R U . . .
C5 C 0.7752(6) 0.7165(3) 0.7788(2) 0.0589(10) Uani 1 1 d . . . . .
H5 H 0.6773 0.6732 0.7786 0.071 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 1.487(2) . ?
S1 N1 1.688(3) . ?
S1 C13 1.847(4) . ?
F4 C12 1.338(4) . ?
F5 C12 1.347(4) . ?
F6 C12 1.329(4) . ?
N1 C9 1.464(4) . ?
N1 C8 1.468(4) . ?
F3 C1 1.305(5) . ?
F1 C1 1.329(5) . ?
C12 C11 1.496(4) . ?
C8 C7 1.490(4) . ?
C8 C9 1.494(4) . ?
C8 H8 0.9800 . ?
C9 C11 1.519(4) . ?
C9 H9 0.9800 . ?
C7 C6 1.388(5) . ?
C7 C5 1.390(5) . ?
C6 C3 1.388(5) . ?
C6 H6 0.9300 . ?
C2 C4 1.380(5) . ?
C2 C3 1.384(5) . ?
C2 C1 1.495(5) . ?
C1 F2 1.283(6) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C3 H3 0.9300 . ?
C16 C13 1.529(5) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C13 C15 1.516(5) . ?
C13 C14 1.521(5) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C4 C5 1.374(5) . ?
C4 H4 0.9300 . ?
C5 H5 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 N1 112.70(12) . . ?
O1 S1 C13 106.75(16) . . ?
N1 S1 C13 96.73(15) . . ?
C9 N1 C8 61.3(2) . . ?
C9 N1 S1 128.7(2) . . ?
C8 N1 S1 119.6(2) . . ?
F6 C12 F4 106.8(3) . . ?
F6 C12 F5 106.6(3) . . ?
F4 C12 F5 105.0(3) . . ?
F6 C12 C11 112.1(3) . . ?
F4 C12 C11 113.2(3) . . ?
F5 C12 C11 112.5(3) . . ?
N1 C8 C7 116.7(2) . . ?
N1 C8 C9 59.2(2) . . ?
C7 C8 C9 122.0(3) . . ?
N1 C8 H8 115.6 . . ?
C7 C8 H8 115.6 . . ?
C9 C8 H8 115.6 . . ?
N1 C9 C8 59.5(2) . . ?
N1 C9 C11 123.4(2) . . ?
C8 C9 C11 120.1(3) . . ?
N1 C9 H9 114.3 . . ?
C8 C9 H9 114.3 . . ?
C11 C9 H9 114.3 . . ?
C6 C7 C5 119.0(3) . . ?
C6 C7 C8 119.4(3) . . ?
C5 C7 C8 121.5(3) . . ?
C7 C6 C3 120.3(3) . . ?
C7 C6 H6 119.9 . . ?
C3 C6 H6 119.9 . . ?
C4 C2 C3 119.6(3) . . ?
C4 C2 C1 120.8(3) . . ?
C3 C2 C1 119.5(3) . . ?
F2 C1 F3 107.4(5) . . ?
F2 C1 F1 106.0(5) . . ?
F3 C1 F1 103.9(4) . . ?
F2 C1 C2 112.2(4) . . ?
F3 C1 C2 113.7(3) . . ?
F1 C1 C2 113.1(4) . . ?
C12 C11 C9 110.5(3) . . ?
C12 C11 H11A 109.6 . . ?
C9 C11 H11A 109.6 . . ?
C12 C11 H11B 109.6 . . ?
C9 C11 H11B 109.6 . . ?
H11A C11 H11B 108.1 . . ?
C2 C3 C6 120.0(3) . . ?
C2 C3 H3 120.0 . . ?
C6 C3 H3 120.0 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C13 C14 112.4(3) . . ?
C15 C13 C16 111.8(3) . . ?
C14 C13 C16 110.8(3) . . ?
C15 C13 S1 110.6(2) . . ?
C14 C13 S1 107.6(2) . . ?
C16 C13 S1 103.1(3) . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C5 C4 C2 120.5(3) . . ?
C5 C4 H4 119.7 . . ?
C2 C4 H4 119.7 . . ?
C4 C5 C7 120.5(3) . . ?
C4 C5 H5 119.8 . . ?
C7 C5 H5 119.8 . . ?

_refine_diff_density_max         0.481
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.052



####################################################################### 
# 
# 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_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1941437'
loop_
_audit_author_name
_audit_author_address
'shuanglin qin'
;Tianjin University
China
;
_audit_update_record             
;
2019-07-18 deposited with the CCDC.	2020-06-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H20 F3 N O S'
_chemical_formula_weight         319.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   6.2173(3)
_cell_length_b                   7.2888(4)
_cell_length_c                   17.6163(11)
_cell_angle_alpha                90
_cell_angle_beta                 96.159(5)
_cell_angle_gamma                90
_cell_volume                     793.70(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    120.0(1)
_cell_measurement_reflns_used    4188
_cell_measurement_theta_min      5.029
_cell_measurement_theta_max      73.339

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_F_000             336
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    2.092
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.67071
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120.0(1)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean none
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_number            7416
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.523
_diffrn_reflns_theta_max         73.661
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.935
_diffrn_reflns_point_group_measured_fraction_full 0.958
_reflns_number_total             2979
_reflns_number_gt                2877
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.758
_reflns_Friedel_fraction_max     0.879
_reflns_Friedel_fraction_full    0.912

_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 1.171.39.33c (Rigaku OD, 2017)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    wingx
_computing_publication_material  wingx
_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)+(0.0453P)²+0.4863P] 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 
;
 Flack x determined using 1180 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.039(11)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         2979
_refine_ls_number_parameters     194
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0395
_refine_ls_wR_factor_ref         0.1005
_refine_ls_wR_factor_gt          0.0999
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_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
C1 C 0.6911(6) 0.4639(6) 0.5759(2) 0.0371(9) Uani 1 1 d . . . . .
H1 H 0.6618 0.3392 0.5789 0.045 Uiso 1 1 calc R U . . .
C2 C 0.7410(7) 0.5382(8) 0.5074(2) 0.0483(13) Uani 1 1 d . . . . .
H2 H 0.7431 0.4635 0.4647 0.058 Uiso 1 1 calc R U . . .
C3 C 0.7877(7) 0.7230(8) 0.5026(2) 0.0471(11) Uani 1 1 d . . . . .
H3 H 0.8229 0.7721 0.4568 0.057 Uiso 1 1 calc R U . . .
C4 C 0.7821(7) 0.8341(7) 0.5653(3) 0.0447(10) Uani 1 1 d . . . . .
H4 H 0.8129 0.9585 0.5619 0.054 Uiso 1 1 calc R U . . .
C5 C 0.7304(6) 0.7609(6) 0.6339(2) 0.0353(9) Uani 1 1 d . . . . .
H5 H 0.7264 0.8369 0.6762 0.042 Uiso 1 1 calc R U . . .
C6 C 0.6844(5) 0.5742(7) 0.63986(18) 0.0302(7) Uani 1 1 d . . . . .
C7 C 0.6348(5) 0.4905(5) 0.7136(2) 0.0279(7) Uani 1 1 d . . . . .
H7 H 0.7091 0.3742 0.7265 0.033 Uiso 1 1 calc R U . . .
C8 C 0.4226(5) 0.5124(5) 0.74558(19) 0.0251(7) Uani 1 1 d . . . . .
C9 C 0.3396(6) 0.3518(5) 0.7896(2) 0.0284(8) Uani 1 1 d . . . . .
H9A H 0.4580 0.3041 0.8243 0.034 Uiso 1 1 calc R U . . .
H9B H 0.2299 0.3967 0.8202 0.034 Uiso 1 1 calc R U . . .
C10 C 0.2457(6) 0.1983(5) 0.7404(2) 0.0308(8) Uani 1 1 d . . . . .
C11 C 0.2514(6) 0.6352(5) 0.7060(2) 0.0289(8) Uani 1 1 d . . . . .
H11A H 0.1527 0.6717 0.7415 0.043 Uiso 1 1 calc R U . . .
H11B H 0.1740 0.5702 0.6642 0.043 Uiso 1 1 calc R U . . .
H11C H 0.3183 0.7420 0.6870 0.043 Uiso 1 1 calc R U . . .
C12 C 0.6782(6) 0.7525(5) 0.9189(2) 0.0274(7) Uani 1 1 d . . . . .
C13 C 0.8119(7) 0.7291(6) 0.9965(2) 0.0368(9) Uani 1 1 d . . . . .
H13A H 0.7806 0.6120 1.0177 0.055 Uiso 1 1 calc R U . . .
H13B H 0.7760 0.8248 1.0303 0.055 Uiso 1 1 calc R U . . .
H13C H 0.9631 0.7358 0.9900 0.055 Uiso 1 1 calc R U . . .
C14 C 0.7228(7) 0.9383(6) 0.8841(2) 0.0374(9) Uani 1 1 d . . . . .
H14A H 0.8745 0.9490 0.8790 0.056 Uiso 1 1 calc R U . . .
H14B H 0.6802 1.0343 0.9167 0.056 Uiso 1 1 calc R U . . .
H14C H 0.6419 0.9485 0.8347 0.056 Uiso 1 1 calc R U . . .
C15 C 0.4386(6) 0.7209(6) 0.9241(2) 0.0341(8) Uani 1 1 d . . . . .
H15A H 0.3582 0.7505 0.8761 0.051 Uiso 1 1 calc R U . . .
H15B H 0.3912 0.7977 0.9634 0.051 Uiso 1 1 calc R U . . .
H15C H 0.4149 0.5946 0.9362 0.051 Uiso 1 1 calc R U . . .
F1 F 0.3874(4) 0.1248(3) 0.69650(14) 0.0414(6) Uani 1 1 d . . . . .
F2 F 0.0719(4) 0.2454(3) 0.69231(14) 0.0420(6) Uani 1 1 d . . . . .
F3 F 0.1819(4) 0.0604(4) 0.78344(13) 0.0459(6) Uani 1 1 d . . . . .
N1 N 0.6186(5) 0.6126(4) 0.77827(16) 0.0279(7) Uani 1 1 d . . . . .
O1 O 0.7485(5) 0.3960(4) 0.89557(16) 0.0408(7) Uani 1 1 d . . . . .
S1 S 0.78649(12) 0.57549(13) 0.85904(4) 0.0285(2) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.386(6) . ?
C1 C6 1.389(6) . ?
C1 H1 0.9300 . ?
C2 C3 1.382(8) . ?
C2 H2 0.9300 . ?
C3 C4 1.374(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.389(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.397(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.497(5) . ?
C7 N1 1.458(4) . ?
C7 C8 1.497(5) . ?
C7 H7 0.9800 . ?
C8 N1 1.483(4) . ?
C8 C11 1.503(5) . ?
C8 C9 1.524(5) . ?
C9 C10 1.495(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 F3 1.344(4) . ?
C10 F2 1.345(4) . ?
C10 F1 1.345(4) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C15 1.520(5) . ?
C12 C14 1.524(5) . ?
C12 C13 1.530(5) . ?
C12 S1 1.840(4) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
N1 S1 1.694(3) . ?
O1 S1 1.488(3) . ?

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
C2 C1 C6 120.6(4) . . ?
C2 C1 H1 119.7 . . ?
C6 C1 H1 119.7 . . ?
C3 C2 C1 120.1(4) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C4 C3 C2 120.1(4) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 120.1(5) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C6 120.5(4) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 118.6(4) . . ?
C1 C6 C7 119.7(4) . . ?
C5 C6 C7 121.7(4) . . ?
N1 C7 C6 117.8(3) . . ?
N1 C7 C8 60.2(2) . . ?
C6 C7 C8 123.7(3) . . ?
N1 C7 H7 114.7 . . ?
C6 C7 H7 114.7 . . ?
C8 C7 H7 114.7 . . ?
N1 C8 C7 58.6(2) . . ?
N1 C8 C11 113.4(3) . . ?
C7 C8 C11 119.8(3) . . ?
N1 C8 C9 119.3(3) . . ?
C7 C8 C9 118.0(3) . . ?
C11 C8 C9 115.6(3) . . ?
C10 C9 C8 114.3(3) . . ?
C10 C9 H9A 108.7 . . ?
C8 C9 H9A 108.7 . . ?
C10 C9 H9B 108.7 . . ?
C8 C9 H9B 108.7 . . ?
H9A C9 H9B 107.6 . . ?
F3 C10 F2 106.3(3) . . ?
F3 C10 F1 106.1(3) . . ?
F2 C10 F1 105.7(3) . . ?
F3 C10 C9 110.7(3) . . ?
F2 C10 C9 114.3(3) . . ?
F1 C10 C9 113.1(3) . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C15 C12 C14 112.4(3) . . ?
C15 C12 C13 111.8(3) . . ?
C14 C12 C13 110.7(3) . . ?
C15 C12 S1 110.5(3) . . ?
C14 C12 S1 107.4(3) . . ?
C13 C12 S1 103.7(3) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C7 N1 C8 61.2(2) . . ?
C7 N1 S1 118.1(2) . . ?
C8 N1 S1 130.8(2) . . ?
O1 S1 N1 113.05(16) . . ?
O1 S1 C12 106.49(18) . . ?
N1 S1 C12 98.00(15) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.9(6) . . . . ?
C1 C2 C3 C4 -0.8(7) . . . . ?
C2 C3 C4 C5 0.3(6) . . . . ?
C3 C4 C5 C6 0.2(6) . . . . ?
C2 C1 C6 C5 -0.4(5) . . . . ?
C2 C1 C6 C7 -178.7(4) . . . . ?
C4 C5 C6 C1 -0.1(5) . . . . ?
C4 C5 C6 C7 178.1(3) . . . . ?
C1 C6 C7 N1 -177.0(3) . . . . ?
C5 C6 C7 N1 4.8(5) . . . . ?
C1 C6 C7 C8 -105.8(4) . . . . ?
C5 C6 C7 C8 76.0(5) . . . . ?
C6 C7 C8 N1 -105.4(4) . . . . ?
N1 C7 C8 C11 100.8(3) . . . . ?
C6 C7 C8 C11 -4.6(5) . . . . ?
N1 C7 C8 C9 -109.0(3) . . . . ?
C6 C7 C8 C9 145.7(4) . . . . ?
N1 C8 C9 C10 -144.3(3) . . . . ?
C7 C8 C9 C10 -76.6(4) . . . . ?
C11 C8 C9 C10 74.9(4) . . . . ?
C8 C9 C10 F3 178.3(3) . . . . ?
C8 C9 C10 F2 -61.7(4) . . . . ?
C8 C9 C10 F1 59.3(4) . . . . ?
C6 C7 N1 C8 114.9(3) . . . . ?
C6 C7 N1 S1 -121.6(3) . . . . ?
C8 C7 N1 S1 123.5(3) . . . . ?
C11 C8 N1 C7 -111.7(3) . . . . ?
C9 C8 N1 C7 106.7(3) . . . . ?
C7 C8 N1 S1 -103.6(3) . . . . ?
C11 C8 N1 S1 144.7(3) . . . . ?
C9 C8 N1 S1 3.2(5) . . . . ?
C7 N1 S1 O1 -64.0(3) . . . . ?
C8 N1 S1 O1 10.9(4) . . . . ?
C7 N1 S1 C12 -175.8(3) . . . . ?
C8 N1 S1 C12 -100.9(3) . . . . ?
C15 C12 S1 O1 -59.1(3) . . . . ?
C14 C12 S1 O1 178.0(3) . . . . ?
C13 C12 S1 O1 60.8(3) . . . . ?
C15 C12 S1 N1 57.9(3) . . . . ?
C14 C12 S1 N1 -65.0(3) . . . . ?
C13 C12 S1 N1 177.8(3) . . . . ?

_refine_diff_density_max         0.357
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.050



