# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2142067'
loop_
_audit_author_name
_audit_author_address
'jianchao Cui'
;College of Chemistry, Fuzhou University Fuzhou
China
;
_audit_update_record             
;
2022-01-14 deposited with the CCDC.	2022-05-10 downloaded from the CCDC.
;
_audit_creation_date             2021-11-12
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H9 F O3 S'
_chemical_formula_sum            'C10 H9 F O3 S'
_chemical_formula_weight         228.23
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_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                   10.2088(6)
_cell_length_b                   11.1724(5)
_cell_length_c                   8.9589(5)
_cell_angle_alpha                90
_cell_angle_beta                 108.436(2)
_cell_angle_gamma                90
_cell_volume                     969.38(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6473
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      24.99
_cell_measurement_theta_min      2.78
_shelx_estimated_absorpt_T_max   0.968
_shelx_estimated_absorpt_T_min   0.968
_exptl_absorpt_coefficient_mu    0.331
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_unetI/netI     0.0193
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            15025
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.037
_diffrn_reflns_theta_max         25.037
_diffrn_reflns_theta_min         2.103
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1482
_reflns_number_total             1711
_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       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.453
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         1711
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0367
_refine_ls_restrained_S_all      1.044
_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)+(0.0473P)²+0.7110P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0935
_refine_ls_wR_factor_ref         0.0976
_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 Ternary CH refined with riding coordinates:
 C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C8(H8), C9(H9), C7(H7)
;
_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 0.94635(5) 0.70429(5) 0.70639(7) 0.0359(2) Uani 1 1 d . . . . .
F1 F 1.06703(13) 0.66704(14) 0.84356(17) 0.0514(4) Uani 1 1 d . . . . .
O1 O 0.66423(15) 0.74368(13) 0.51875(17) 0.0334(4) Uani 1 1 d . . . . .
O3 O 0.95044(16) 0.63824(16) 0.57009(17) 0.0414(4) Uani 1 1 d . . . . .
O2 O 0.94395(17) 0.83138(15) 0.6911(2) 0.0482(5) Uani 1 1 d . . . . .
C3 C 0.54481(19) 0.62357(17) 0.6521(2) 0.0217(4) Uani 1 1 d . . . . .
C4 C 0.5572(2) 0.53410(17) 0.7649(2) 0.0233(4) Uani 1 1 d . . . . .
C2 C 0.6684(2) 0.67925(17) 0.6295(2) 0.0239(4) Uani 1 1 d . . . . .
C10 C 0.4149(2) 0.66470(18) 0.5608(2) 0.0261(4) Uani 1 1 d . . . . .
H10 H 0.407820 0.723111 0.484693 0.031 Uiso 1 1 calc R U . . .
C8 C 0.3083(2) 0.5293(2) 0.6940(3) 0.0323(5) Uani 1 1 d . . . . .
H8 H 0.229027 0.497512 0.708493 0.039 Uiso 1 1 calc R U . . .
C6 C 0.8138(2) 0.52293(18) 0.8066(2) 0.0291(5) Uani 1 1 d . . . . .
H6A H 0.810298 0.474228 0.715776 0.035 Uiso 1 1 calc R U . . .
H6B H 0.901295 0.508153 0.887575 0.035 Uiso 1 1 calc R U . . .
C1 C 0.8025(2) 0.65467(18) 0.7612(2) 0.0263(5) Uani 1 1 d . . . . .
H1 H 0.800661 0.701003 0.853399 0.032 Uiso 1 1 calc R U . . .
C9 C 0.2972(2) 0.6188(2) 0.5834(2) 0.0317(5) Uani 1 1 d . . . . .
H9 H 0.210821 0.647702 0.524849 0.038 Uiso 1 1 calc R U . . .
C5 C 0.6957(2) 0.48960(19) 0.8671(2) 0.0291(5) Uani 1 1 d . . . . .
H5A H 0.692077 0.403137 0.874792 0.035 Uiso 1 1 calc R U . . .
H5B H 0.714084 0.522124 0.972085 0.035 Uiso 1 1 calc R U . . .
C7 C 0.4362(2) 0.48722(18) 0.7825(2) 0.0293(5) Uani 1 1 d . . . . .
H7 H 0.441970 0.426493 0.855328 0.035 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 F1 1.4978(15) . ?
S1 O3 1.4386(16) . ?
S1 O2 1.4260(18) . ?
S1 C1 1.778(2) . ?
O1 C2 1.216(2) . ?
C3 C4 1.398(3) . ?
C3 C2 1.477(3) . ?
C3 C10 1.397(3) . ?
C4 C5 1.505(3) . ?
C4 C7 1.397(3) . ?
C2 C1 1.523(3) . ?
C10 H10 0.9300 . ?
C10 C9 1.379(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.386(3) . ?
C8 C7 1.378(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C1 1.522(3) . ?
C6 C5 1.517(3) . ?
C1 H1 0.9800 . ?
C9 H9 0.9300 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C7 H7 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
F1 S1 C1 102.93(9) . . ?
O3 S1 F1 108.47(10) . . ?
O3 S1 C1 108.83(10) . . ?
O2 S1 F1 109.89(10) . . ?
O2 S1 O3 115.68(11) . . ?
O2 S1 C1 110.26(10) . . ?
C4 C3 C2 120.93(17) . . ?
C10 C3 C4 120.70(18) . . ?
C10 C3 C2 118.35(17) . . ?
C3 C4 C5 121.94(17) . . ?
C7 C4 C3 117.95(18) . . ?
C7 C4 C5 120.11(18) . . ?
O1 C2 C3 123.39(18) . . ?
O1 C2 C1 122.01(17) . . ?
C3 C2 C1 114.53(16) . . ?
C3 C10 H10 120.0 . . ?
C9 C10 C3 120.08(19) . . ?
C9 C10 H10 120.0 . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C7 C8 C9 120.38(19) . . ?
H6A C6 H6B 108.3 . . ?
C1 C6 H6A 109.8 . . ?
C1 C6 H6B 109.8 . . ?
C5 C6 H6A 109.8 . . ?
C5 C6 H6B 109.8 . . ?
C5 C6 C1 109.34(17) . . ?
S1 C1 H1 107.8 . . ?
C2 C1 S1 110.39(14) . . ?
C2 C1 H1 107.8 . . ?
C6 C1 S1 112.07(14) . . ?
C6 C1 C2 110.81(16) . . ?
C6 C1 H1 107.8 . . ?
C10 C9 C8 119.67(19) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C4 C5 C6 113.68(16) . . ?
C4 C5 H5A 108.8 . . ?
C4 C5 H5B 108.8 . . ?
C6 C5 H5A 108.8 . . ?
C6 C5 H5B 108.8 . . ?
H5A C5 H5B 107.7 . . ?
C4 C7 H7 119.4 . . ?
C8 C7 C4 121.19(19) . . ?
C8 C7 H7 119.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 S1 C1 C2 -176.88(13) . . . . ?
F1 S1 C1 C6 -52.85(16) . . . . ?
O1 C2 C1 S1 -12.6(2) . . . . ?
O1 C2 C1 C6 -137.32(19) . . . . ?
O3 S1 C1 C2 -61.94(16) . . . . ?
O3 S1 C1 C6 62.09(17) . . . . ?
O2 S1 C1 C2 65.93(17) . . . . ?
O2 S1 C1 C6 -170.03(15) . . . . ?
C3 C4 C5 C6 -16.5(3) . . . . ?
C3 C4 C7 C8 -1.3(3) . . . . ?
C3 C2 C1 S1 170.31(13) . . . . ?
C3 C2 C1 C6 45.6(2) . . . . ?
C3 C10 C9 C8 -1.8(3) . . . . ?
C4 C3 C2 O1 168.56(19) . . . . ?
C4 C3 C2 C1 -14.4(3) . . . . ?
C4 C3 C10 C9 1.3(3) . . . . ?
C2 C3 C4 C5 -0.5(3) . . . . ?
C2 C3 C4 C7 178.58(17) . . . . ?
C2 C3 C10 C9 -177.06(17) . . . . ?
C10 C3 C4 C5 -178.83(18) . . . . ?
C10 C3 C4 C7 0.3(3) . . . . ?
C10 C3 C2 O1 -13.1(3) . . . . ?
C10 C3 C2 C1 164.00(17) . . . . ?
C1 C6 C5 C4 46.7(2) . . . . ?
C9 C8 C7 C4 0.8(3) . . . . ?
C5 C4 C7 C8 177.81(18) . . . . ?
C5 C6 C1 S1 174.50(14) . . . . ?
C5 C6 C1 C2 -61.7(2) . . . . ?
C7 C4 C5 C6 164.47(18) . . . . ?
C7 C8 C9 C10 0.8(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
