# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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_d8v21630
_database_code_depnum_ccdc_archive 'CCDC 2122882'
loop_
_audit_author_name
_audit_author_address
'Xiaoyu Ma'
;Shanghai Institute of Technology
China
;
_audit_update_record             
;
2021-11-18 deposited with the CCDC.	2023-08-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H11 F O2 S'
_chemical_formula_weight         202.24

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

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

_cell_length_a                   13.407(2)
_cell_length_b                   7.2877(13)
_cell_length_c                   9.8840(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     965.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2439
_cell_measurement_theta_min      8.791
_cell_measurement_theta_max      54.833

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_F_000             424
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.314
_shelx_estimated_absorpt_T_min   0.940
_shelx_estimated_absorpt_T_max   0.963
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6345
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4423
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.395
_diffrn_reflns_theta_max         25.994
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.974
_reflns_number_total             1006
_reflns_number_gt                859
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0657P)²+0.1681P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.16(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1006
_refine_ls_number_parameters     107
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0402
_refine_ls_wR_factor_ref         0.1253
_refine_ls_wR_factor_gt          0.1178
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_restrained_S_all      1.120
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.59647(5) 0.2500 0.73558(6) 0.0718(4) Uani 1 2 d S T P . .
O1 O 0.50379(18) 0.2500 0.7980(2) 0.1145(10) Uani 1 2 d S T P A .
F1 F 0.6669(11) 0.399(2) 0.7641(15) 0.092(3) Uani 0.5 1 d . U P A 1
O2 O 0.6455(15) 0.424(2) 0.7810(17) 0.086(3) Uani 0.5 1 d . U P A 2
C1 C 0.58958(15) 0.2500 0.5585(2) 0.0491(6) Uani 1 2 d S T P A .
C2 C 0.49654(16) 0.2500 0.4938(2) 0.0481(5) Uani 1 2 d S T P . .
C3 C 0.49722(18) 0.2500 0.3537(2) 0.0569(6) Uani 1 2 d S T P A .
H3 H 0.4364 0.2500 0.3085 0.068 Uiso 1 2 calc R U P . .
C4 C 0.58322(19) 0.2500 0.2781(2) 0.0611(7) Uani 1 2 d S T P . .
C5 C 0.6732(2) 0.2500 0.3453(3) 0.0648(7) Uani 1 2 d S T P A .
H5 H 0.7318 0.2500 0.2948 0.078 Uiso 1 2 calc R U P . .
C6 C 0.67972(17) 0.2500 0.4855(3) 0.0580(6) Uani 1 2 d S T P . .
C7 C 0.7827(2) 0.2500 0.5463(5) 0.0934(11) Uani 1 2 d DS T P A .
C8 C 0.39590(19) 0.2500 0.5624(3) 0.0680(7) Uani 1 2 d S T P A .
C9 C 0.5786(4) 0.2500 0.1253(3) 0.0960(12) Uani 1 2 d DS T P A .
H7A H 0.830(2) 0.2500 0.476(3) 0.126(14) Uiso 1 2 d DS . P . .
H8A H 0.3864(14) 0.146(3) 0.626(2) 0.090(7) Uiso 1 1 d . . . . .
H9A H 0.5419(19) 0.148(3) 0.093(3) 0.147(11) Uiso 1 1 d D . . . .
H7B H 0.7920(19) 0.158(3) 0.612(2) 0.134(11) Uiso 1 1 d D . . . .
H8B H 0.340(3) 0.2500 0.497(4) 0.096(10) Uiso 1 2 d S . P . .
H9B H 0.644(2) 0.2500 0.080(5) 0.19(2) Uiso 1 2 d DS . P . .


_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 1.387(2) . ?
S1 F1 1.466(16) . ?
S1 F1 1.466(16) 7_565 ?
S1 O2 1.495(19) 7_565 ?
S1 O2 1.495(19) . ?
S1 C1 1.753(2) . ?
C1 C2 1.402(3) . ?
C1 C6 1.408(3) . ?
C2 C3 1.385(3) . ?
C2 C8 1.510(3) . ?
C3 C4 1.374(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.377(4) . ?
C4 C9 1.512(4) . ?
C5 C6 1.389(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.506(4) . ?
C7 H7A 0.943(19) . ?
C7 H7B 0.939(17) . ?
C8 H8A 0.99(2) . ?
C8 H8B 0.99(4) . ?
C9 H9A 0.946(17) . ?
C9 H9B 0.98(2) . ?

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 F1 119.4(5) . . ?
O1 S1 F1 119.4(5) . 7_565 ?
F1 S1 F1 95.6(11) . 7_565 ?
O1 S1 O2 105.1(7) . 7_565 ?
O1 S1 O2 105.1(7) . . ?
O2 S1 O2 115.6(14) 7_565 . ?
O1 S1 C1 113.39(12) . . ?
F1 S1 C1 103.1(6) . . ?
F1 S1 C1 103.1(6) 7_565 . ?
O2 S1 C1 108.9(7) 7_565 . ?
O2 S1 C1 108.9(7) . . ?
C2 C1 C6 122.0(2) . . ?
C2 C1 S1 120.14(16) . . ?
C6 C1 S1 117.82(16) . . ?
C3 C2 C1 116.7(2) . . ?
C3 C2 C8 117.1(2) . . ?
C1 C2 C8 126.2(2) . . ?
C4 C3 C2 123.3(2) . . ?
C4 C3 H3 118.3 . . ?
C2 C3 H3 118.3 . . ?
C3 C4 C5 118.2(2) . . ?
C3 C4 C9 120.6(3) . . ?
C5 C4 C9 121.2(3) . . ?
C4 C5 C6 122.4(2) . . ?
C4 C5 H5 118.8 . . ?
C6 C5 H5 118.8 . . ?
C5 C6 C1 117.2(2) . . ?
C5 C6 C7 117.2(3) . . ?
C1 C6 C7 125.6(2) . . ?
C6 C7 H7A 109(2) . . ?
C6 C7 H7B 113.3(17) . . ?
H7A C7 H7B 115(2) . . ?
C2 C8 H8A 113.5(11) . . ?
C2 C8 H8B 112.3(19) . . ?
H8A C8 H8B 108.6(17) . . ?
C4 C9 H9A 111(2) . . ?
C4 C9 H9B 115(3) . . ?
H9A C9 H9B 108(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
O1 S1 C1 C2 0.000(0) . . . . ?
F1 S1 C1 C2 -130.5(5) . . . . ?
F1 S1 C1 C2 130.5(5) 7_565 . . . ?
O2 S1 C1 C2 116.6(7) 7_565 . . . ?
O2 S1 C1 C2 -116.6(7) . . . . ?
O1 S1 C1 C6 180.000(0) . . . . ?
F1 S1 C1 C6 49.5(5) . . . . ?
F1 S1 C1 C6 -49.5(5) 7_565 . . . ?
O2 S1 C1 C6 -63.4(7) 7_565 . . . ?
O2 S1 C1 C6 63.4(7) . . . . ?
C6 C1 C2 C3 0.000(0) . . . . ?
S1 C1 C2 C3 180.000(0) . . . . ?
C6 C1 C2 C8 180.000(0) . . . . ?
S1 C1 C2 C8 0.000(0) . . . . ?
C1 C2 C3 C4 0.000(0) . . . . ?
C8 C2 C3 C4 180.000(0) . . . . ?
C2 C3 C4 C5 0.000(0) . . . . ?
C2 C3 C4 C9 180.000(0) . . . . ?
C3 C4 C5 C6 0.000(0) . . . . ?
C9 C4 C5 C6 180.000(0) . . . . ?
C4 C5 C6 C1 0.000(0) . . . . ?
C4 C5 C6 C7 180.000(0) . . . . ?
C2 C1 C6 C5 0.000(0) . . . . ?
S1 C1 C6 C5 180.000(0) . . . . ?
C2 C1 C6 C7 180.000(0) . . . . ?
S1 C1 C6 C7 0.000(1) . . . . ?

_refine_diff_density_max         0.184
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.030

_shelxl_version_number           2013-4

