# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

####################################################################### 
# 
# 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_A_a
_database_code_depnum_ccdc_archive 'CCDC 2192921'
loop_
_audit_author_name
_audit_author_address
'Jian Wen'
;jiangnan university
China
;
_audit_update_record             
;
2022-07-27 deposited with the CCDC.	2023-05-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H15 I S'
_chemical_formula_weight         330.21

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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                   9.0770(15)
_cell_length_b                   6.3879(10)
_cell_length_c                   22.529(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.329(6)
_cell_angle_gamma                90
_cell_volume                     1289.0(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5661
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      27.42

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.702
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    2.613
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_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            11036
_diffrn_reflns_av_unetI/netI     0.0773
_diffrn_reflns_av_R_equivalents  0.0770
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.310
_diffrn_reflns_theta_max         27.533
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             2945
_reflns_number_gt                2571
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.1000P)²+0.9737P] 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         2945
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0432
_refine_ls_wR_factor_ref         0.1244
_refine_ls_wR_factor_gt          0.1177
_refine_ls_goodness_of_fit_ref   0.813
_refine_ls_restrained_S_all      0.813
_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
I1 I 0.97372(3) 1.10967(4) 0.36154(2) 0.03945(14) Uani 1 1 d . . . . .
S1 S 0.33471(12) 0.28529(15) 0.43863(4) 0.0383(2) Uani 1 1 d . . . . .
C1 C 0.7763(4) 0.9341(6) 0.34250(15) 0.0321(7) Uani 1 1 d . . . . .
C2 C 0.5169(4) 0.6867(5) 0.32569(14) 0.0287(6) Uani 1 1 d . . . . .
C3 C 0.7814(4) 0.7304(6) 0.32214(16) 0.0347(7) Uani 1 1 d . . . . .
H3 H 0.870438 0.675638 0.313514 0.042 Uiso 1 1 calc R U . . .
C6 C 0.6542(5) 0.6085(5) 0.31464(17) 0.0346(8) Uani 1 1 d . . . . .
H6 H 0.659685 0.470630 0.301917 0.042 Uiso 1 1 calc R U . . .
C7 C 0.3797(4) 0.5535(6) 0.31914(15) 0.0328(7) Uani 1 1 d . . . . .
C9 C 0.2620(4) 0.6088(5) 0.35695(17) 0.0343(8) Uani 1 1 d . . . . .
H9A H 0.172353 0.528798 0.342809 0.041 Uiso 1 1 calc R U . . .
H9B H 0.237375 0.755971 0.351443 0.041 Uiso 1 1 calc R U . . .
C10 C 0.3109(4) 0.5659(6) 0.42395(16) 0.0340(7) Uani 1 1 d . . . . .
H10 H 0.406308 0.636546 0.437355 0.041 Uiso 1 1 calc R U . . .
C4 C 0.5139(5) 0.8952(5) 0.34444(18) 0.0344(8) Uani 1 1 d . . . . .
H4 H 0.424106 0.952599 0.351359 0.041 Uiso 1 1 calc R U . . .
C5 C 0.6413(4) 1.0185(5) 0.35298(16) 0.0353(7) Uani 1 1 d . . . . .
H5 H 0.636694 1.156595 0.365623 0.042 Uiso 1 1 calc R U . . .
C8 C 0.3615(5) 0.3888(6) 0.28272(19) 0.0416(9) Uani 1 1 d . . . . .
H8A H 0.435369 0.353282 0.260322 0.050 Uiso 1 1 calc R U . . .
H8B H 0.274955 0.308889 0.279615 0.050 Uiso 1 1 calc R U . . .
C11 C 0.1982(6) 0.6385(7) 0.4633(2) 0.0457(10) Uani 1 1 d . . . . .
H11A H 0.207275 0.788014 0.470505 0.055 Uiso 1 1 calc R U . . .
H11B H 0.097199 0.608335 0.443809 0.055 Uiso 1 1 calc R U . . .
C12 C 0.2342(5) 0.5187(8) 0.52234(17) 0.0494(10) Uani 1 1 d . . . . .
H12A H 0.327023 0.568579 0.545449 0.059 Uiso 1 1 calc R U . . .
H12B H 0.155144 0.537415 0.546141 0.059 Uiso 1 1 calc R U . . .
C13 C 0.2477(5) 0.2908(7) 0.50621(17) 0.0462(10) Uani 1 1 d . . . . .
H13A H 0.149973 0.225562 0.498514 0.055 Uiso 1 1 calc R U . . .
H13B H 0.308907 0.216395 0.538783 0.055 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
I1 C1 2.099(4) . ?
S1 C13 1.826(4) . ?
S1 C10 1.830(4) . ?
C1 C3 1.383(5) . ?
C1 C5 1.393(5) . ?
C2 C4 1.398(5) . ?
C2 C6 1.402(5) . ?
C2 C7 1.496(5) . ?
C3 C6 1.380(6) . ?
C3 H3 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.328(5) . ?
C7 C9 1.512(5) . ?
C9 C10 1.527(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.530(5) . ?
C10 H10 0.9800 . ?
C4 C5 1.387(5) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C8 H8A 0.9300 . ?
C8 H8B 0.9300 . ?
C11 C12 1.523(6) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.510(7) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?

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
C13 S1 C10 94.43(19) . . ?
C3 C1 C5 119.9(3) . . ?
C3 C1 I1 119.8(3) . . ?
C5 C1 I1 120.2(3) . . ?
C4 C2 C6 117.0(3) . . ?
C4 C2 C7 121.0(3) . . ?
C6 C2 C7 122.0(3) . . ?
C6 C3 C1 119.9(3) . . ?
C6 C3 H3 120.0 . . ?
C1 C3 H3 120.0 . . ?
C3 C6 C2 121.8(3) . . ?
C3 C6 H6 119.1 . . ?
C2 C6 H6 119.1 . . ?
C8 C7 C2 122.0(4) . . ?
C8 C7 C9 120.3(4) . . ?
C2 C7 C9 117.7(3) . . ?
C7 C9 C10 113.4(3) . . ?
C7 C9 H9A 108.9 . . ?
C10 C9 H9A 108.9 . . ?
C7 C9 H9B 108.9 . . ?
C10 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
C9 C10 C11 113.9(3) . . ?
C9 C10 S1 111.2(3) . . ?
C11 C10 S1 105.2(3) . . ?
C9 C10 H10 108.8 . . ?
C11 C10 H10 108.8 . . ?
S1 C10 H10 108.8 . . ?
C5 C4 C2 121.8(3) . . ?
C5 C4 H4 119.1 . . ?
C2 C4 H4 119.1 . . ?
C4 C5 C1 119.5(3) . . ?
C4 C5 H5 120.2 . . ?
C1 C5 H5 120.2 . . ?
C7 C8 H8A 120.0 . . ?
C7 C8 H8B 120.0 . . ?
H8A C8 H8B 120.0 . . ?
C12 C11 C10 106.6(4) . . ?
C12 C11 H11A 110.4 . . ?
C10 C11 H11A 110.4 . . ?
C12 C11 H11B 110.4 . . ?
C10 C11 H11B 110.4 . . ?
H11A C11 H11B 108.6 . . ?
C13 C12 C11 106.8(3) . . ?
C13 C12 H12A 110.4 . . ?
C11 C12 H12A 110.4 . . ?
C13 C12 H12B 110.4 . . ?
C11 C12 H12B 110.4 . . ?
H12A C12 H12B 108.6 . . ?
C12 C13 S1 106.4(3) . . ?
C12 C13 H13A 110.4 . . ?
S1 C13 H13A 110.4 . . ?
C12 C13 H13B 110.4 . . ?
S1 C13 H13B 110.4 . . ?
H13A C13 H13B 108.6 . . ?

_refine_diff_density_max         0.669
_refine_diff_density_min         -0.831
_refine_diff_density_rms         0.140

####################################################################### 
# 
# 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_dbdxz_auto
_database_code_depnum_ccdc_archive 'CCDC 2259304'
loop_
_audit_author_name
_audit_author_address
'Jian Wen'
;jiangnan university
China
;
_audit_update_record             
;
2023-04-27 deposited with the CCDC.	2023-05-27 downloaded from the CCDC.
;
_audit_creation_date             2023-04-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        1
_chemical_formula_moiety         'C17 H19 S, C F3 O3 S'
_chemical_formula_sum            'C18 H19 F3 O3 S2'
_chemical_formula_weight         404.45
_chemical_melting_point          ?
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'
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   14.2669(8)
_cell_length_b                   11.9380(6)
_cell_length_c                   12.6553(6)
_cell_angle_alpha                90
_cell_angle_beta                 112.820(7)
_cell_angle_gamma                90
_cell_volume                     1986.7(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5365
_cell_measurement_temperature    293
_cell_measurement_theta_max      66.0960
_cell_measurement_theta_min      3.3609
_shelx_estimated_absorpt_T_max   0.872
_shelx_estimated_absorpt_T_min   0.827
_exptl_absorpt_coefficient_mu    2.814
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.24680
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.89a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1124
_diffrn_reflns_av_unetI/netI     0.0654
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            15019
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.270
_diffrn_reflns_theta_min         3.361
_diffrn_ambient_temperature      293
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -11.00  22.00   0.50    0.50    --   42.30 -54.00  90.00   66
  2  ω     37.00  63.00   0.50    0.50    --   42.30 -54.00 -30.00   52
  3  ω     35.00  70.00   0.50    0.50    --   42.30 -82.00-120.00   70
  4  ω     36.00  61.00   0.50    0.50    --   42.30 -54.00  90.00   50
  5  ω    -46.00   9.00   0.50    0.50    --   42.30 -77.00-180.00  110
  6  ω    -46.00  68.00   0.50    0.50    --   42.30 -82.00 -30.00  228
  7  ω     13.00  68.00   0.50    0.50    --   42.30 -82.00 120.00  110
  8  ω    -19.00  36.00   0.50    0.50    --   42.30 -54.00-150.00  110
  9  ω    -32.00  13.00   0.50    0.50    --   42.30 -54.00 -30.00   90
 10  ω     13.00 132.00   0.50    0.50    --   42.30  43.00-180.00  238
 11  ω    -46.00 -21.00   0.50    0.50    --   42.30 -54.00  90.00   50
 12  ω     17.00  66.00   0.50    0.50    --   42.30 -77.00-180.00   98
 13  ω     -4.00  22.00   0.50    0.50    --   42.30 -77.00-150.00   52
 14  ω     21.00  46.00   0.50    0.50    --   42.30 -77.00   0.00   50
 15  ω     12.00  70.00   0.50    0.50    --   42.30 -82.00   0.00  116
 16  ω    -19.00   6.00   0.50    0.50    --   42.30 -82.00   0.00   50
 17  ω     49.00 132.00   0.50    0.50    --   42.30  65.00  60.00  166
 18  ω    -47.00 -21.00   0.50    0.50    --   42.30 -82.00 120.00   52
 19  ω    -19.00   6.00   0.50    0.50    --   42.30 -82.00-120.00   50
 20  ω      4.00  91.00   0.50    0.50    --   93.70 -59.00 -90.00  174
 21  ω      4.00  98.00   0.50    0.50    --   93.70 -82.00 -90.00  188
 22  ω      5.00  86.00   0.50    0.50    --   93.70 -59.00 120.00  162
 23  ω    113.00 139.00   0.50    0.50    --   93.70  42.00-150.00   52
 24  ω     76.00 108.00   0.50    0.50    --   93.70 -82.00 -60.00   64
 25  ω     82.00 127.00   0.50    0.50    --   93.70 -33.00 -90.00   90
 26  ω     74.00 100.00   0.50    0.50    --   93.70 -82.00   0.00   52
 27  ω     12.00  67.00   0.50    0.50    --   93.70 -82.00   0.00  110
 28  ω     65.00  96.00   0.50    0.50    --   93.70 -82.00-180.00   62
 29  ω      4.00  93.00   0.50    0.50    --   93.70 -82.00  90.00  178
 30  ω     34.00  93.00   0.50    0.50    --   93.70 -82.00-120.00  118
 31  ω     68.00 126.00   0.50    0.50    --   93.70 -33.00 120.00  116
 32  ω     16.00 183.00   0.50    0.50    --   93.70   0.00-180.00  334
 33  ω     71.00  96.00   0.50    0.50    --   93.70 -82.00-150.00   50
 34  ω      8.00  67.00   0.50    0.50    --   93.70 -82.00-150.00  118
 35  ω     71.00  96.00   0.50    0.50    --   93.70 -82.00 -30.00   50
 36  ω    103.00 128.00   0.50    0.50    --   93.70  77.00  60.00   50
 37  ω     18.00  64.00   0.50    0.50    --   93.70 -82.00  60.00   92
 38  ω     10.00  61.00   0.50    0.50    --   93.70 -33.00 120.00  102
 39  ω     10.00  24.50   0.50    0.50    --   93.70 -33.00 -90.00   29
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0536962000
_diffrn_orient_matrix_UB_12      -0.0983665000
_diffrn_orient_matrix_UB_13      0.0792207000
_diffrn_orient_matrix_UB_21      0.0937507000
_diffrn_orient_matrix_UB_22      0.0165507000
_diffrn_orient_matrix_UB_23      -0.0303461000
_diffrn_orient_matrix_UB_31      0.0453926000
_diffrn_orient_matrix_UB_32      0.0820020000
_diffrn_orient_matrix_UB_33      0.1010558000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2504
_reflns_number_total             3554
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.695
_refine_diff_density_min         -0.510
_refine_diff_density_rms         0.099
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.252
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3554
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1196
_refine_ls_R_factor_gt           0.1047
_refine_ls_restrained_S_all      1.252
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3049
_refine_ls_wR_factor_ref         0.3351
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12),
 C13(H13), C14(H14), C15(H15)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.53119(9) 0.75119(10) 0.52255(9) 0.0934(5) Uani 1 1 d . . . . .
C1 C 0.7059(4) 0.9054(5) 0.3180(4) 0.0954(13) Uani 1 1 d . . . . .
H1 H 0.652766 0.855818 0.281803 0.114 Uiso 1 1 calc R U . . .
C2 C 0.7520(5) 0.9604(5) 0.2555(6) 0.1169(18) Uani 1 1 d . . . . .
H2 H 0.728872 0.947981 0.176987 0.140 Uiso 1 1 calc R U . . .
C3 C 0.8302(6) 1.0324(5) 0.3056(7) 0.1214(19) Uani 1 1 d . . . . .
H3 H 0.859747 1.069689 0.261712 0.146 Uiso 1 1 calc R U . . .
C4 C 0.8657(5) 1.0498(5) 0.4232(7) 0.121(2) Uani 1 1 d . . . . .
H4 H 0.921171 1.096493 0.459280 0.145 Uiso 1 1 calc R U . . .
C5 C 0.8177(4) 0.9967(5) 0.4870(5) 0.1095(16) Uani 1 1 d . . . . .
H5 H 0.839607 1.011197 0.565109 0.131 Uiso 1 1 calc R U . . .
C6 C 0.7394(3) 0.9242(4) 0.4368(3) 0.0788(10) Uani 1 1 d . . . . .
C7 C 0.6906(3) 0.8625(3) 0.5042(3) 0.0783(10) Uani 1 1 d . . . . .
C8 C 0.7522(4) 0.8451(5) 0.6307(3) 0.0956(14) Uani 1 1 d . . . . .
H8A H 0.766045 0.917872 0.667690 0.115 Uiso 1 1 calc R U . . .
H8B H 0.710923 0.803621 0.662676 0.115 Uiso 1 1 calc R U . . .
C9 C 0.8502(3) 0.7853(4) 0.6606(3) 0.0795(11) Uani 1 1 d . . . . .
C10 C 0.8686(4) 0.7097(5) 0.5896(4) 0.0987(14) Uani 1 1 d . . . . .
H10 H 0.817623 0.694321 0.518539 0.118 Uiso 1 1 calc R U . . .
C11 C 0.9619(5) 0.6553(6) 0.6214(5) 0.1207(19) Uani 1 1 d . . . . .
H11 H 0.975072 0.609346 0.569414 0.145 Uiso 1 1 calc R U . . .
C12 C 1.0345(5) 0.6702(6) 0.7305(6) 0.1237(19) Uani 1 1 d . . . . .
H12 H 1.095145 0.630177 0.754404 0.148 Uiso 1 1 calc R U . . .
C13 C 1.0170(5) 0.7434(6) 0.8027(6) 0.132(2) Uani 1 1 d . . . . .
H13 H 1.066653 0.754700 0.875610 0.158 Uiso 1 1 calc R U . . .
C14 C 0.9261(4) 0.8014(5) 0.7690(4) 0.1077(16) Uani 1 1 d . . . . .
H14 H 0.915643 0.851769 0.819351 0.129 Uiso 1 1 calc R U . . .
C15 C 0.5933(3) 0.8297(4) 0.4526(4) 0.0850(11) Uani 1 1 d . . . . .
H15 H 0.557474 0.849660 0.376414 0.102 Uiso 1 1 calc R U . . .
C16 C 0.4426(5) 0.6726(4) 0.4051(5) 0.1090(16) Uani 1 1 d . . . . .
H16A H 0.404982 0.722820 0.344127 0.163 Uiso 1 1 calc R U . . .
H16B H 0.396488 0.633102 0.430437 0.163 Uiso 1 1 calc R U . . .
H16C H 0.479004 0.619896 0.377984 0.163 Uiso 1 1 calc R U . . .
C17 C 0.4479(4) 0.8499(4) 0.5433(5) 0.1010(14) Uani 1 1 d . . . . .
H17A H 0.486239 0.901895 0.602094 0.151 Uiso 1 1 calc R U . . .
H17B H 0.399472 0.811867 0.566071 0.151 Uiso 1 1 calc R U . . .
H17C H 0.412757 0.889742 0.473098 0.151 Uiso 1 1 calc R U . . .
S2 S 0.36653(9) 0.53747(10) 0.67501(10) 0.0932(5) Uani 1 1 d . . . . .
F1 F 0.2344(4) 0.5865(9) 0.4800(4) 0.275(4) Uani 1 1 d . . . . .
F2 F 0.2346(4) 0.6928(5) 0.6050(9) 0.249(4) Uani 1 1 d . . . . .
F3 F 0.1711(2) 0.5319(4) 0.5943(4) 0.1478(15) Uani 1 1 d . . . . .
O1 O 0.3602(5) 0.4252(6) 0.6392(10) 0.260(5) Uani 1 1 d . . . . .
O2 O 0.4378(3) 0.6091(5) 0.6643(4) 0.1390(17) Uani 1 1 d . . . . .
O3 O 0.3655(5) 0.5482(6) 0.7862(4) 0.199(3) Uani 1 1 d . . . . .
C18 C 0.2450(5) 0.5901(7) 0.5890(7) 0.130(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
S1 C15 1.749(5) . ?
S1 C16 1.797(6) . ?
S1 C17 1.764(5) . ?
C1 H1 0.9300 . ?
C1 C2 1.376(7) . ?
C1 C6 1.409(6) . ?
C2 H2 0.9300 . ?
C2 C3 1.355(9) . ?
C3 H3 0.9300 . ?
C3 C4 1.390(10) . ?
C4 H4 0.9300 . ?
C4 C5 1.397(9) . ?
C5 H5 0.9300 . ?
C5 C6 1.360(7) . ?
C6 C7 1.488(6) . ?
C7 C8 1.513(6) . ?
C7 C15 1.342(6) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.482(6) . ?
C9 C10 1.368(6) . ?
C9 C14 1.393(6) . ?
C10 H10 0.9300 . ?
C10 C11 1.393(7) . ?
C11 H11 0.9300 . ?
C11 C12 1.379(9) . ?
C12 H12 0.9300 . ?
C12 C13 1.355(10) . ?
C13 H13 0.9300 . ?
C13 C14 1.383(9) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
S2 O1 1.406(6) . ?
S2 O2 1.375(4) . ?
S2 O3 1.418(6) . ?
S2 C18 1.767(7) . ?
F1 C18 1.328(9) . ?
F2 C18 1.261(10) . ?
F3 C18 1.286(8) . ?

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
C15 S1 C16 101.1(2) . . ?
C15 S1 C17 102.7(2) . . ?
C17 S1 C16 100.0(3) . . ?
C2 C1 H1 120.1 . . ?
C2 C1 C6 119.8(5) . . ?
C6 C1 H1 120.1 . . ?
C1 C2 H2 119.2 . . ?
C3 C2 C1 121.7(6) . . ?
C3 C2 H2 119.2 . . ?
C2 C3 H3 120.4 . . ?
C2 C3 C4 119.2(6) . . ?
C4 C3 H3 120.4 . . ?
C3 C4 H4 120.2 . . ?
C3 C4 C5 119.6(6) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 H5 119.4 . . ?
C6 C5 C4 121.1(6) . . ?
C6 C5 H5 119.4 . . ?
C1 C6 C7 119.5(4) . . ?
C5 C6 C1 118.5(5) . . ?
C5 C6 C7 122.0(4) . . ?
C6 C7 C8 117.7(4) . . ?
C15 C7 C6 119.4(4) . . ?
C15 C7 C8 122.8(4) . . ?
C7 C8 H8A 108.3 . . ?
C7 C8 H8B 108.3 . . ?
H8A C8 H8B 107.4 . . ?
C9 C8 C7 116.1(3) . . ?
C9 C8 H8A 108.3 . . ?
C9 C8 H8B 108.3 . . ?
C10 C9 C8 123.5(4) . . ?
C10 C9 C14 117.6(4) . . ?
C14 C9 C8 118.8(4) . . ?
C9 C10 H10 119.2 . . ?
C9 C10 C11 121.6(4) . . ?
C11 C10 H10 119.2 . . ?
C10 C11 H11 120.3 . . ?
C12 C11 C10 119.4(6) . . ?
C12 C11 H11 120.3 . . ?
C11 C12 H12 120.2 . . ?
C13 C12 C11 119.6(5) . . ?
C13 C12 H12 120.2 . . ?
C12 C13 H13 119.6 . . ?
C12 C13 C14 120.7(5) . . ?
C14 C13 H13 119.6 . . ?
C9 C14 H14 119.6 . . ?
C13 C14 C9 120.9(6) . . ?
C13 C14 H14 119.6 . . ?
S1 C15 H15 118.6 . . ?
C7 C15 S1 122.8(3) . . ?
C7 C15 H15 118.6 . . ?
S1 C16 H16A 109.5 . . ?
S1 C16 H16B 109.5 . . ?
S1 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
S1 C17 H17A 109.5 . . ?
S1 C17 H17B 109.5 . . ?
S1 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O1 S2 O3 112.4(6) . . ?
O1 S2 C18 102.4(4) . . ?
O2 S2 O1 121.2(5) . . ?
O2 S2 O3 109.5(3) . . ?
O2 S2 C18 107.7(3) . . ?
O3 S2 C18 101.2(4) . . ?
F1 C18 S2 108.5(5) . . ?
F2 C18 S2 113.3(6) . . ?
F2 C18 F1 103.0(8) . . ?
F2 C18 F3 111.5(6) . . ?
F3 C18 S2 113.8(6) . . ?
F3 C18 F1 105.8(7) . . ?

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
C1 C2 C3 C4 0.9(10) . . . . ?
C1 C6 C7 C8 154.7(4) . . . . ?
C1 C6 C7 C15 -28.6(6) . . . . ?
C2 C1 C6 C5 -0.4(8) . . . . ?
C2 C1 C6 C7 -178.7(5) . . . . ?
C2 C3 C4 C5 -2.7(10) . . . . ?
C3 C4 C5 C6 3.0(9) . . . . ?
C4 C5 C6 C1 -1.4(8) . . . . ?
C4 C5 C6 C7 176.9(5) . . . . ?
C5 C6 C7 C8 -23.6(6) . . . . ?
C5 C6 C7 C15 153.1(5) . . . . ?
C6 C1 C2 C3 0.6(9) . . . . ?
C6 C7 C8 C9 -57.7(6) . . . . ?
C6 C7 C15 S1 176.9(3) . . . . ?
C7 C8 C9 C10 -27.2(7) . . . . ?
C7 C8 C9 C14 156.7(5) . . . . ?
C8 C7 C15 S1 -6.5(6) . . . . ?
C8 C9 C10 C11 -179.9(6) . . . . ?
C8 C9 C14 C13 176.9(6) . . . . ?
C9 C10 C11 C12 5.8(10) . . . . ?
C10 C9 C14 C13 0.5(8) . . . . ?
C10 C11 C12 C13 -4.6(11) . . . . ?
C11 C12 C13 C14 1.5(11) . . . . ?
C12 C13 C14 C9 0.5(10) . . . . ?
C14 C9 C10 C11 -3.7(8) . . . . ?
C15 C7 C8 C9 125.7(5) . . . . ?
C16 S1 C15 C7 -149.7(4) . . . . ?
C17 S1 C15 C7 107.2(4) . . . . ?
O1 S2 C18 F1 -64.3(9) . . . . ?
O1 S2 C18 F2 -178.1(8) . . . . ?
O1 S2 C18 F3 53.1(8) . . . . ?
O2 S2 C18 F1 64.6(8) . . . . ?
O2 S2 C18 F2 -49.2(7) . . . . ?
O2 S2 C18 F3 -178.0(5) . . . . ?
O3 S2 C18 F1 179.4(7) . . . . ?
O3 S2 C18 F2 65.7(7) . . . . ?
O3 S2 C18 F3 -63.1(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.604
_oxdiff_exptl_absorpt_empirical_full_min 0.371
####################################################################### 
# 
# 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_jn1_auto
_database_code_depnum_ccdc_archive 'CCDC 2253421'
loop_
_audit_author_name
_audit_author_address
'Jian Wen'
;jiangnan university
China
;
_audit_update_record             
;
2023-04-02 deposited with the CCDC.	2023-05-27 downloaded from the CCDC.
;
_audit_creation_date             2023-04-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        1
_chemical_formula_moiety         'C17 H23 S, C F3 O3 S'
_chemical_formula_sum            'C18 H23 F3 O3 S2'
_chemical_formula_weight         408.48
_chemical_melting_point          ?
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'
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   9.89231(14)
_cell_length_b                   8.53641(10)
_cell_length_c                   23.7023(3)
_cell_angle_alpha                90
_cell_angle_beta                 101.8925(13)
_cell_angle_gamma                90
_cell_volume                     1958.57(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10689
_cell_measurement_temperature    293
_cell_measurement_theta_max      67.9490
_cell_measurement_theta_min      1.8690
_shelx_estimated_absorpt_T_max   0.894
_shelx_estimated_absorpt_T_min   0.847
_exptl_absorpt_coefficient_mu    2.855
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.02858
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.89a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            15882
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.103
_diffrn_reflns_theta_min         3.812
_diffrn_ambient_temperature      293
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     67.00 131.00   0.50    0.50    --   42.30  65.00 -30.00  128
  2  ω     55.00  81.00   0.50    0.50    --   42.30  82.00 150.00   52
  3  ω     -4.00  24.00   0.50    0.50    --   42.30 -77.00  30.00   56
  4  ω    -37.00  24.00   0.50    0.50    --   42.30 -82.00 -60.00  122
  5  ω     29.00  67.00   0.50    0.50    --   42.30 -82.00  60.00   76
  6  ω     21.00  67.00   0.50    0.50    --   42.30 -82.00 -30.00   92
  7  ω    -44.00   0.00   0.50    0.50    --   42.30 -65.00  90.00   88
  8  ω    -36.00  17.00   0.50    0.50    --   42.30 -82.00-120.00  106
  9  ω    100.00 130.00   0.50    0.50    --   42.30  82.00 150.00   60
 10  ω    -39.00   1.00   0.50    0.50    --   42.30 -77.00-180.00   80
 11  ω     26.00  61.00   0.50    0.50    --   42.30  65.00 -30.00   70
 12  ω    -47.00  -3.00   0.50    0.50    --   42.30 -82.00  60.00   88
 13  ω    -43.00   8.00   0.50    0.50    --   42.30 -82.00   0.00  102
 14  ω     40.00 131.00   0.50    0.50    --   42.30  54.00  90.00  182
 15  ω      7.00  32.00   0.50    0.50    --   42.30 -65.00  90.00   50
 16  ω     26.00  69.00   0.50    0.50    --   42.30 -82.00   0.00   86
 17  ω     42.00  67.00   0.50    0.50    --   42.30 -82.00  90.00   50
 18  ω     42.00  69.00   0.50    0.50    --   42.30 -82.00-180.00   54
 19  ω      5.00  31.00   0.50    0.50    --   42.30 -77.00-180.00   52
 20  ω     23.00  57.00   0.50    0.50    --   42.30 -82.00-120.00   68
 21  ω     32.00  57.00   0.50    0.50    --   42.30 -77.00-180.00   50
 22  ω    128.00 154.00   0.50    0.80    --   93.70  33.00 -60.00   52
 23  ω     71.00 103.00   0.50    0.80    --   93.70  33.00 -60.00   64
 24  ω      4.00  84.00   0.50    0.80    --   93.70 -82.00  90.00  160
 25  ω      4.00  32.00   0.50    0.80    --   93.70 -50.00-150.00   56
 26  ω     67.00  93.00   0.50    0.80    --   93.70 -82.00  30.00   52
 27  ω     61.00  87.00   0.50    0.80    --   93.70 -50.00-150.00   52
 28  ω      4.00 105.00   0.50    0.80    --   93.70 -82.00  60.00  202
 29  ω     29.00  61.00   0.50    0.80    --   93.70 -82.00  30.00   64
 30  ω      7.00 100.00   0.50    0.80    --   93.70 -82.00   0.00  186
 31  ω     61.00 183.00   0.50    0.80    --   93.70 -25.00 -90.00  244
 32  ω     16.00  52.00   0.50    0.80    --   93.70 -33.00  60.00   72
 33  ω     76.00 102.00   0.50    0.80    --   93.70 -82.00 -90.00   52
 34  ω     10.00  36.00   0.50    0.80    --   93.70 -82.00 -90.00   52
 35  ω     76.00 101.00   0.50    0.80    --   93.70  68.00  30.00   50
 36  ω      6.00  98.00   0.50    0.80    --   93.70 -82.00 150.00  184
 37  ω      4.00  56.00   0.50    0.80    --   93.70 -25.00 -90.00  104
 38  ω      5.00 121.00   0.50    0.80    --   93.70 -82.00-150.00  232
 39  ω     83.00 109.00   0.50    0.80    --   93.70 -82.00-180.00   52
 40  ω      7.00 129.00   0.50    0.80    --   93.70   8.00-120.00  244
 41  ω      8.00  64.00   0.50    0.80    --   93.70 -82.00-180.00  112
 42  ω     34.00  89.00   0.50    0.80    --   93.70 -82.00 120.00  110
 43  ω    155.00 181.00   0.50    0.80    --   93.70  82.00   0.00   52
 44  ω     61.00  73.50   0.50    0.80    --   93.70 -33.00  60.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0038518000
_diffrn_orient_matrix_UB_12      -0.1780301000
_diffrn_orient_matrix_UB_13      -0.0102378000
_diffrn_orient_matrix_UB_21      -0.1497889000
_diffrn_orient_matrix_UB_22      -0.0139386000
_diffrn_orient_matrix_UB_23      0.0085044000
_diffrn_orient_matrix_UB_31      -0.0536455000
_diffrn_orient_matrix_UB_32      0.0260380000
_diffrn_orient_matrix_UB_33      -0.0650730000
_diffrn_oxdiff_digest_frames     
;
0191ecaa42cd135cd0278e19380cc6a85100031b465
;
_diffrn_oxdiff_digest_hkl        
;
01097f6d2d2cc0b0746148ab75c9a4e288f129
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3201
_reflns_number_total             3477
_reflns_odcompleteness_completeness 97.53
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.366
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3477
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0441
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0741P)²+0.5227P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1229
_refine_ls_wR_factor_ref         0.1250
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C8(H8A,H8B),
 C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C14(H14), C15(H15), C16(H16), C17(H17)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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 0.11757(4) 0.88297(5) 0.43714(2) 0.04267(16) Uani 1 1 d . . . . .
C1 C -0.05720(19) 0.8144(3) 0.43506(9) 0.0516(5) Uani 1 1 d . . . . .
H1A H -0.055590 0.706785 0.448341 0.062 Uiso 1 1 calc R . . . .
H1B H -0.101120 0.878502 0.459912 0.062 Uiso 1 1 calc R . . . .
C2 C -0.1363(2) 0.8256(3) 0.37324(11) 0.0680(6) Uani 1 1 d . . . . .
H2A H -0.195732 0.734922 0.363788 0.082 Uiso 1 1 calc R . . . .
H2B H -0.193837 0.918714 0.368379 0.082 Uiso 1 1 calc R . . . .
C3 C -0.0346(3) 0.8333(4) 0.33374(11) 0.0811(8) Uani 1 1 d . . . . .
H3A H -0.078676 0.876129 0.296597 0.097 Uiso 1 1 calc R . . . .
H3B H -0.000578 0.729256 0.327777 0.097 Uiso 1 1 calc R . . . .
C4 C 0.0837(2) 0.9380(3) 0.36251(10) 0.0631(6) Uani 1 1 d . . . . .
H4A H 0.057578 1.047533 0.357924 0.076 Uiso 1 1 calc R . . . .
H4B H 0.164590 0.920940 0.346097 0.076 Uiso 1 1 calc R . . . .
C5 C 0.21226(18) 0.6994(2) 0.43832(8) 0.0435(4) Uani 1 1 d . . . . .
H5A H 0.218396 0.649008 0.475449 0.052 Uiso 1 1 calc R . . . .
H5B H 0.162280 0.629844 0.408899 0.052 Uiso 1 1 calc R . . . .
C6 C 0.35621(18) 0.7258(2) 0.42781(8) 0.0437(4) Uani 1 1 d . . . . .
C7 C 0.46152(19) 0.7463(2) 0.47274(9) 0.0457(4) Uani 1 1 d . . . . .
C8 C 0.4490(2) 0.7498(3) 0.53528(9) 0.0538(5) Uani 1 1 d . . . . .
H8A H 0.417260 0.649617 0.546832 0.065 Uiso 1 1 calc R . . . .
H8B H 0.385037 0.830736 0.541702 0.065 Uiso 1 1 calc R . . . .
C9 C 0.5956(2) 0.7854(3) 0.56879(11) 0.0671(6) Uani 1 1 d . . . . .
H9A H 0.610488 0.897439 0.573350 0.081 Uiso 1 1 calc R . . . .
H9B H 0.612599 0.736763 0.606575 0.081 Uiso 1 1 calc R . . . .
C10 C 0.6872(2) 0.7154(3) 0.53150(11) 0.0661(6) Uani 1 1 d . . . . .
H10A H 0.779162 0.760379 0.540643 0.079 Uiso 1 1 calc R . . . .
H10B H 0.694115 0.602618 0.536299 0.079 Uiso 1 1 calc R . . . .
C11 C 0.6139(2) 0.7583(3) 0.47103(10) 0.0558(5) Uani 1 1 d . . . . .
H11A H 0.637772 0.686000 0.443049 0.067 Uiso 1 1 calc R . . . .
H11B H 0.637554 0.863834 0.461357 0.067 Uiso 1 1 calc R . . . .
C12 C 0.3733(2) 0.7235(3) 0.36670(9) 0.0509(5) Uani 1 1 d . . . . .
C13 C 0.4543(2) 0.8358(3) 0.34626(10) 0.0579(5) Uani 1 1 d . . . . .
H13 H 0.500125 0.911245 0.371447 0.069 Uiso 1 1 calc R . . . .
C14 C 0.4676(3) 0.8368(4) 0.28915(12) 0.0747(7) Uani 1 1 d . . . . .
H14 H 0.522744 0.911814 0.276502 0.090 Uiso 1 1 calc R . . . .
C15 C 0.3996(4) 0.7276(4) 0.25134(13) 0.0931(10) Uani 1 1 d . . . . .
H15 H 0.407040 0.729441 0.212861 0.112 Uiso 1 1 calc R . . . .
C16 C 0.3208(4) 0.6160(4) 0.27052(13) 0.0936(10) Uani 1 1 d . . . . .
H16 H 0.275719 0.541095 0.244898 0.112 Uiso 1 1 calc R . . . .
C17 C 0.3070(3) 0.6126(3) 0.32782(11) 0.0711(7) Uani 1 1 d . . . . .
H17 H 0.253122 0.535601 0.340094 0.085 Uiso 1 1 calc R . . . .
S2 S 0.10709(5) 0.65982(6) 0.60050(2) 0.05060(17) Uani 1 1 d . . . . .
F1 F 0.2030(2) 0.7896(3) 0.70073(7) 0.1025(6) Uani 1 1 d . . . . .
F2 F 0.2618(3) 0.5549(3) 0.69505(9) 0.1315(8) Uani 1 1 d . . . . .
F3 F 0.35615(18) 0.7365(4) 0.65481(8) 0.1308(9) Uani 1 1 d . . . . .
O1 O -0.00886(18) 0.6099(3) 0.62285(8) 0.0854(6) Uani 1 1 d . . . . .
O2 O 0.0957(2) 0.8114(2) 0.57403(8) 0.0784(5) Uani 1 1 d . . . . .
O3 O 0.16463(19) 0.5450(2) 0.56839(7) 0.0714(5) Uani 1 1 d . . . . .
C18 C 0.2403(3) 0.6856(3) 0.66537(10) 0.0665(6) 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
S1 C1 1.8163(19) . ?
S1 C4 1.794(2) . ?
S1 C5 1.8232(18) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.515(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.511(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.518(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.512(2) . ?
C6 C7 1.339(3) . ?
C6 C12 1.492(3) . ?
C7 C8 1.513(3) . ?
C7 C11 1.520(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.533(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.513(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.512(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.398(3) . ?
C12 C17 1.388(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.387(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.370(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.367(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.393(4) . ?
C17 H17 0.9300 . ?
S2 O1 1.4243(18) . ?
S2 O2 1.4322(18) . ?
S2 O3 1.4294(17) . ?
S2 C18 1.820(2) . ?
F1 C18 1.324(3) . ?
F2 C18 1.313(3) . ?
F3 C18 1.297(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
C1 S1 C5 101.91(9) . . ?
C4 S1 C1 94.27(10) . . ?
C4 S1 C5 103.37(10) . . ?
S1 C1 H1A 110.2 . . ?
S1 C1 H1B 110.2 . . ?
H1A C1 H1B 108.5 . . ?
C2 C1 S1 107.76(15) . . ?
C2 C1 H1A 110.2 . . ?
C2 C1 H1B 110.2 . . ?
C1 C2 H2A 109.9 . . ?
C1 C2 H2B 109.9 . . ?
H2A C2 H2B 108.3 . . ?
C3 C2 C1 108.93(19) . . ?
C3 C2 H2A 109.9 . . ?
C3 C2 H2B 109.9 . . ?
C2 C3 H3A 110.3 . . ?
C2 C3 H3B 110.3 . . ?
C2 C3 C4 107.3(2) . . ?
H3A C3 H3B 108.5 . . ?
C4 C3 H3A 110.3 . . ?
C4 C3 H3B 110.3 . . ?
S1 C4 H4A 110.7 . . ?
S1 C4 H4B 110.8 . . ?
C3 C4 S1 104.98(17) . . ?
C3 C4 H4A 110.8 . . ?
C3 C4 H4B 110.8 . . ?
H4A C4 H4B 108.8 . . ?
S1 C5 H5A 109.3 . . ?
S1 C5 H5B 109.3 . . ?
H5A C5 H5B 108.0 . . ?
C6 C5 S1 111.54(13) . . ?
C6 C5 H5A 109.3 . . ?
C6 C5 H5B 109.3 . . ?
C7 C6 C5 119.54(17) . . ?
C7 C6 C12 123.27(17) . . ?
C12 C6 C5 117.17(16) . . ?
C6 C7 C8 125.08(18) . . ?
C6 C7 C11 126.95(18) . . ?
C8 C7 C11 107.84(17) . . ?
C7 C8 H8A 110.8 . . ?
C7 C8 H8B 110.8 . . ?
C7 C8 C9 104.61(18) . . ?
H8A C8 H8B 108.9 . . ?
C9 C8 H8A 110.8 . . ?
C9 C8 H8B 110.8 . . ?
C8 C9 H9A 111.0 . . ?
C8 C9 H9B 111.0 . . ?
H9A C9 H9B 109.0 . . ?
C10 C9 C8 103.60(19) . . ?
C10 C9 H9A 111.0 . . ?
C10 C9 H9B 111.0 . . ?
C9 C10 H10A 111.1 . . ?
C9 C10 H10B 111.1 . . ?
H10A C10 H10B 109.1 . . ?
C11 C10 C9 103.30(18) . . ?
C11 C10 H10A 111.1 . . ?
C11 C10 H10B 111.1 . . ?
C7 C11 H11A 110.9 . . ?
C7 C11 H11B 110.9 . . ?
C10 C11 C7 104.05(18) . . ?
C10 C11 H11A 110.9 . . ?
C10 C11 H11B 110.9 . . ?
H11A C11 H11B 109.0 . . ?
C13 C12 C6 120.97(19) . . ?
C17 C12 C6 121.4(2) . . ?
C17 C12 C13 117.6(2) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 C12 121.2(2) . . ?
C14 C13 H13 119.4 . . ?
C13 C14 H14 119.9 . . ?
C15 C14 C13 120.1(3) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 H15 120.2 . . ?
C16 C15 C14 119.6(3) . . ?
C16 C15 H15 120.2 . . ?
C15 C16 H16 119.5 . . ?
C15 C16 C17 121.1(3) . . ?
C17 C16 H16 119.5 . . ?
C12 C17 C16 120.4(3) . . ?
C12 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
O1 S2 O2 115.89(13) . . ?
O1 S2 O3 115.61(12) . . ?
O1 S2 C18 102.72(11) . . ?
O2 S2 C18 103.81(12) . . ?
O3 S2 O2 112.98(12) . . ?
O3 S2 C18 103.56(12) . . ?
F1 C18 S2 111.62(18) . . ?
F2 C18 S2 111.03(19) . . ?
F2 C18 F1 105.4(2) . . ?
F3 C18 S2 113.08(17) . . ?
F3 C18 F1 105.7(2) . . ?
F3 C18 F2 109.6(3) . . ?

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
S1 C1 C2 C3 19.7(3) . . . . ?
S1 C5 C6 C7 92.28(19) . . . . ?
S1 C5 C6 C12 -89.27(18) . . . . ?
C1 S1 C4 C3 -26.45(19) . . . . ?
C1 S1 C5 C6 168.30(14) . . . . ?
C1 C2 C3 C4 -40.2(3) . . . . ?
C2 C3 C4 S1 41.9(2) . . . . ?
C4 S1 C1 C2 4.26(18) . . . . ?
C4 S1 C5 C6 70.92(16) . . . . ?
C5 S1 C1 C2 -100.38(17) . . . . ?
C5 S1 C4 C3 76.88(18) . . . . ?
C5 C6 C7 C8 -1.8(3) . . . . ?
C5 C6 C7 C11 173.54(18) . . . . ?
C5 C6 C12 C13 136.2(2) . . . . ?
C5 C6 C12 C17 -42.2(3) . . . . ?
C6 C7 C8 C9 -176.8(2) . . . . ?
C6 C7 C11 C10 -158.0(2) . . . . ?
C6 C12 C13 C14 -178.2(2) . . . . ?
C6 C12 C17 C16 177.8(3) . . . . ?
C7 C6 C12 C13 -45.4(3) . . . . ?
C7 C6 C12 C17 136.2(2) . . . . ?
C7 C8 C9 C10 -29.5(2) . . . . ?
C8 C7 C11 C10 18.0(2) . . . . ?
C8 C9 C10 C11 40.9(2) . . . . ?
C9 C10 C11 C7 -36.2(2) . . . . ?
C11 C7 C8 C9 7.1(2) . . . . ?
C12 C6 C7 C8 179.86(19) . . . . ?
C12 C6 C7 C11 -4.8(3) . . . . ?
C12 C13 C14 C15 0.7(4) . . . . ?
C13 C12 C17 C16 -0.7(4) . . . . ?
C13 C14 C15 C16 -1.2(5) . . . . ?
C14 C15 C16 C17 0.8(6) . . . . ?
C15 C16 C17 C12 0.1(5) . . . . ?
C17 C12 C13 C14 0.3(3) . . . . ?
O1 S2 C18 F1 -59.1(2) . . . . ?
O1 S2 C18 F2 58.3(2) . . . . ?
O1 S2 C18 F3 -178.0(2) . . . . ?
O2 S2 C18 F1 62.0(2) . . . . ?
O2 S2 C18 F2 179.4(2) . . . . ?
O2 S2 C18 F3 -56.9(3) . . . . ?
O3 S2 C18 F1 -179.74(18) . . . . ?
O3 S2 C18 F2 -62.4(2) . . . . ?
O3 S2 C18 F3 61.3(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 19.266
_oxdiff_exptl_absorpt_empirical_full_min 0.487
