# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

####################################################################### 
# 
# 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 2299742'
loop_
_audit_author_name
_audit_author_address
'Han Z.G.'
;H
China
;
_audit_update_record             
;
2023-10-07 deposited with the CCDC.	2024-02-09 downloaded from the CCDC.
;
_audit_creation_date             2023-09-28
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.06.28 svn.raecde09e for OlexSys, GUI svn.r6132)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H10 F N O2 S'
_chemical_formula_sum            'C12 H10 F N O2 S'
_chemical_formula_weight         251.27
_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'
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'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.0924(9)
_cell_length_b                   8.3336(9)
_cell_length_c                   9.4677(10)
_cell_angle_alpha                70.159(7)
_cell_angle_beta                 73.480(7)
_cell_angle_gamma                86.855(7)
_cell_volume                     575.18(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3021
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      63.33
_cell_measurement_theta_min      5.18
_shelx_estimated_absorpt_T_max   0.733
_shelx_estimated_absorpt_T_min   0.701
_exptl_absorpt_coefficient_mu    2.550
_exptl_absorpt_correction_T_max  0.7524
_exptl_absorpt_correction_T_min  0.4951
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1430 before and 0.0872 after correction.
The Ratio of minimum to maximum transmission is 0.6580.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             260
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0497
_diffrn_reflns_av_unetI/netI     0.0575
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4717
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        63.596
_diffrn_reflns_theta_max         63.596
_diffrn_reflns_theta_min         5.178
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1463
_reflns_number_total             1880
_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 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.398
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         1849
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0658
_refine_ls_R_factor_gt           0.0497
_refine_ls_restrained_S_all      1.103
_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)+(0.0781P)²+0.1229P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1343
_refine_ls_wR_factor_ref         0.1469
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C3(H3), C4(H4), C1(H1)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
;
_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 0.87637(10) 0.82248(9) 0.54539(9) 0.0549(3) Uani 1 1 d . . . . .
F1 F 0.3675(3) -0.0578(2) 0.7498(2) 0.0773(6) Uani 1 1 d . . . . .
O2 O 0.9843(2) 0.6068(2) 0.1616(2) 0.0551(6) Uani 1 1 d . . . . .
O1 O 1.0126(3) 0.8211(3) 0.2426(3) 0.0761(7) Uani 1 1 d . . . . .
N1 N 0.6722(3) 0.5436(3) 0.6868(3) 0.0458(6) Uani 1 1 d . . . . .
C5 C 0.5978(3) 0.3953(3) 0.6976(3) 0.0423(6) Uani 1 1 d . . . . .
C6 C 0.6347(3) 0.3323(3) 0.5715(3) 0.0401(6) Uani 1 1 d . . . . .
C8 C 0.8270(3) 0.5809(3) 0.4175(3) 0.0408(6) Uani 1 1 d . . . . .
C7 C 0.7534(3) 0.4312(3) 0.4305(3) 0.0423(6) Uani 1 1 d . . . . .
H7 H 0.781990 0.393605 0.344942 0.051 Uiso 1 1 calc R U . . .
C10 C 0.9507(3) 0.6844(3) 0.2678(3) 0.0463(7) Uani 1 1 d . . . . .
C9 C 0.7821(3) 0.6330(3) 0.5540(3) 0.0425(6) Uani 1 1 d . . . . .
C2 C 0.4437(4) 0.0936(4) 0.7300(4) 0.0541(7) Uani 1 1 d . . . . .
C3 C 0.4027(4) 0.1514(4) 0.8561(3) 0.0548(8) Uani 1 1 d . . . . .
H3 H 0.324255 0.089472 0.950179 0.066 Uiso 1 1 calc R U . . .
C4 C 0.4793(4) 0.3010(4) 0.8401(3) 0.0534(7) Uani 1 1 d . . . . .
H4 H 0.453016 0.341094 0.924051 0.064 Uiso 1 1 calc R U . . .
C1 C 0.5562(3) 0.1782(3) 0.5893(3) 0.0491(7) Uani 1 1 d . . . . .
H1 H 0.580490 0.135097 0.507338 0.059 Uiso 1 1 calc R U . . .
C11 C 1.1077(4) 0.6975(4) 0.0141(3) 0.0666(9) Uani 1 1 d . . . . .
H11A H 1.115396 0.638363 -0.058497 0.100 Uiso 1 1 calc R U . . .
H11B H 1.218691 0.703345 0.030319 0.100 Uiso 1 1 calc R U . . .
H11C H 1.070782 0.811020 -0.027388 0.100 Uiso 1 1 calc R U . . .
C12 C 0.7957(5) 0.8110(4) 0.7462(4) 0.0665(9) Uani 1 1 d . . . . .
H12A H 0.841053 0.907683 0.758974 0.100 Uiso 1 1 calc R U . . .
H12B H 0.831033 0.707781 0.812127 0.100 Uiso 1 1 calc R U . . .
H12C H 0.672033 0.811550 0.774769 0.100 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 C9 1.758(3) . ?
S1 C12 1.797(3) . ?
F1 C2 1.365(3) . ?
O2 C10 1.330(3) . ?
O2 C11 1.446(3) . ?
O1 C10 1.190(3) . ?
N1 C5 1.364(3) . ?
N1 C9 1.314(3) . ?
C5 C6 1.413(4) . ?
C5 C4 1.409(4) . ?
C6 C7 1.412(4) . ?
C6 C1 1.401(4) . ?
C8 C7 1.364(4) . ?
C8 C10 1.488(4) . ?
C8 C9 1.445(4) . ?
C7 H7 0.9300 . ?
C2 C3 1.385(4) . ?
C2 C1 1.357(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.366(4) . ?
C4 H4 0.9300 . ?
C1 H1 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 S1 C12 100.67(14) . . ?
C10 O2 C11 115.2(2) . . ?
C9 N1 C5 119.2(2) . . ?
N1 C5 C6 122.7(2) . . ?
N1 C5 C4 118.8(2) . . ?
C4 C5 C6 118.6(2) . . ?
C7 C6 C5 116.7(2) . . ?
C1 C6 C5 120.4(2) . . ?
C1 C6 C7 122.9(3) . . ?
C7 C8 C10 120.5(2) . . ?
C7 C8 C9 117.7(2) . . ?
C9 C8 C10 121.7(2) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 C6 121.2(3) . . ?
C8 C7 H7 119.4 . . ?
O2 C10 C8 111.9(2) . . ?
O1 C10 O2 122.9(3) . . ?
O1 C10 C8 125.2(3) . . ?
N1 C9 S1 117.8(2) . . ?
N1 C9 C8 122.5(2) . . ?
C8 C9 S1 119.7(2) . . ?
F1 C2 C3 117.7(3) . . ?
C1 C2 F1 118.7(3) . . ?
C1 C2 C3 123.5(3) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 C2 118.9(3) . . ?
C4 C3 H3 120.6 . . ?
C5 C4 H4 119.7 . . ?
C3 C4 C5 120.6(3) . . ?
C3 C4 H4 119.7 . . ?
C6 C1 H1 121.0 . . ?
C2 C1 C6 118.0(3) . . ?
C2 C1 H1 121.0 . . ?
O2 C11 H11A 109.5 . . ?
O2 C11 H11B 109.5 . . ?
O2 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
S1 C12 H12A 109.5 . . ?
S1 C12 H12B 109.5 . . ?
S1 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

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 C2 C3 C4 178.9(2) . . . . ?
F1 C2 C1 C6 -179.3(2) . . . . ?
N1 C5 C6 C7 -0.3(4) . . . . ?
N1 C5 C6 C1 179.2(2) . . . . ?
N1 C5 C4 C3 -179.6(3) . . . . ?
C5 N1 C9 S1 -179.53(17) . . . . ?
C5 N1 C9 C8 0.3(4) . . . . ?
C5 C6 C7 C8 -0.6(4) . . . . ?
C5 C6 C1 C2 0.6(4) . . . . ?
C6 C5 C4 C3 0.4(4) . . . . ?
C7 C6 C1 C2 -179.9(2) . . . . ?
C7 C8 C10 O2 -4.3(4) . . . . ?
C7 C8 C10 O1 175.0(3) . . . . ?
C7 C8 C9 S1 178.68(18) . . . . ?
C7 C8 C9 N1 -1.2(4) . . . . ?
C10 C8 C7 C6 -179.5(2) . . . . ?
C10 C8 C9 S1 -0.6(3) . . . . ?
C10 C8 C9 N1 179.6(2) . . . . ?
C9 N1 C5 C6 0.4(4) . . . . ?
C9 N1 C5 C4 -179.5(2) . . . . ?
C9 C8 C7 C6 1.3(4) . . . . ?
C9 C8 C10 O2 175.0(2) . . . . ?
C9 C8 C10 O1 -5.8(5) . . . . ?
C2 C3 C4 C5 0.2(4) . . . . ?
C3 C2 C1 C6 0.0(4) . . . . ?
C4 C5 C6 C7 179.6(2) . . . . ?
C4 C5 C6 C1 -0.8(4) . . . . ?
C1 C6 C7 C8 179.9(2) . . . . ?
C1 C2 C3 C4 -0.4(5) . . . . ?
C11 O2 C10 O1 2.5(4) . . . . ?
C11 O2 C10 C8 -178.3(2) . . . . ?
C12 S1 C9 N1 6.0(2) . . . . ?
C12 S1 C9 C8 -173.9(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
