# 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_230706d
_database_code_depnum_ccdc_archive 'CCDC 2283499'
loop_
_audit_author_name
_audit_author_address
'Jin-Hong Lin'
;Shanghai University
China
;
_audit_update_record             
;
2023-07-21 deposited with the CCDC.	2023-11-13 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H8 F N S'
_chemical_formula_iupac          ?
_chemical_formula_weight         229.26

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
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'
'-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                   12.0647(13)
_cell_length_b                   7.4039(7)
_cell_length_c                   23.560(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2104.5(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7430
_cell_measurement_theta_min      2.4164
_cell_measurement_theta_max      27.4435
_cell_measurement_temperature    150.(2)

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.070
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             944

_exptl_absorpt_coefficient_mu    0.288
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_absorpt_correction_T_min  0.88
_exptl_absorpt_correction_T_max  0.98

_exptl_special_details           
;
;

_diffrn_ambient_temperature      150.(2)

_diffrn_source                   'Microfocus sealed tube'
_diffrn_source_type              'Incoatec Ius 3.0'
_diffrn_source_power             0.07
_diffrn_source_current           1.4
_diffrn_source_voltage           50

_diffrn_radiation_probe          ?
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'Helios MX Multilayer Optic'

_diffrn_measurement_device       ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE DUO PHOTON III'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            41099
_diffrn_reflns_av_R_equivalents  0.1386
_diffrn_reflns_av_unetI/netI     0.0536
_diffrn_reflns_theta_min         2.42
_diffrn_reflns_theta_max         27.56
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30

_refine_special_details          
;
;

_reflns_number_total             2427
_reflns_number_gt                1902
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0381
_refine_ls_wR_factor_gt          0.0988
_refine_ls_wR_factor_ref         0.1045
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_number_reflns         2427
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0515P)²+0.3337P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.260
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
N N 0.0061 0.0033 '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'

_computing_data_collection       'Bruker Instrument Service vV6.2.16'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'XT, VERSION 2018/2'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1365)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.79524(15) 0.4040(2) 0.48527(7) 0.0390(4) Uani d . . . 1 . .
C C2 0.75878(13) 0.33568(19) 0.58272(6) 0.0280(3) Uani d . . . 1 . .
C C3 0.74795(12) 0.29920(19) 0.64023(6) 0.0285(3) Uani d . . . 1 . .
H H3 0.811351 0.273529 0.662741 0.034000 Uiso calc U . R 1 . .
C C4 0.64295(12) 0.30084(18) 0.66433(6) 0.0267(3) Uani d . . . 1 . .
C C5 0.62990(11) 0.27376(19) 0.72657(6) 0.0266(3) Uani d . . . 1 . .
C C6 0.69888(13) 0.15617(19) 0.75626(7) 0.0319(3) Uani d . . . 1 . .
H H6 0.753058 0.088231 0.736245 0.038000 Uiso calc U . R 1 . .
C C7 0.68965(15) 0.1369(2) 0.81448(7) 0.0369(4) Uani d . . . 1 . .
H H7 0.736747 0.054843 0.833962 0.044000 Uiso calc U . R 1 . .
C C8 0.61221(13) 0.2364(2) 0.84455(7) 0.0361(4) Uani d . . . 1 . .
H H8 0.606179 0.223689 0.884554 0.043000 Uiso calc U . R 1 . .
C C9 0.54366(14) 0.3546(2) 0.81553(7) 0.0357(4) Uani d . . . 1 . .
H H9 0.490547 0.423930 0.835829 0.043000 Uiso calc U . R 1 . .
C C10 0.55188(12) 0.37274(19) 0.75717(7) 0.0311(3) Uani d . . . 1 . .
H H10 0.503808 0.453508 0.737787 0.037000 Uiso calc U . R 1 . .
C C11 0.55048(13) 0.33622(19) 0.62955(7) 0.0327(4) Uani d . . . 1 . .
H H11 0.478562 0.335938 0.645972 0.039000 Uiso calc U . R 1 . .
C C12 0.56143(13) 0.3713(2) 0.57221(7) 0.0362(4) Uani d . . . 1 . .
H H12 0.497967 0.394574 0.549486 0.043000 Uiso calc U . R 1 . .
C C13 0.66682(14) 0.37212(19) 0.54829(7) 0.0317(3) Uani d . . . 1 . .
F F1 0.84417(10) 0.43447(16) 0.43548(4) 0.0572(3) Uani d . . . 1 . .
N N1 0.69085(13) 0.41037(19) 0.49130(6) 0.0403(3) Uani d . . . 1 . .
S S1 0.87973(3) 0.35350(6) 0.54239(2) 0.03597(15) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N1 . 1.268(2) ?
C1 F1 . 1.3324(19) ?
C1 S1 . 1.7293(17) ?
C2 C3 . 1.388(2) ?
C2 C13 . 1.401(2) ?
C2 S1 . 1.7463(16) ?
C3 C4 . 1.388(2) ?
C3 H3 . 0.950000 ?
C4 C11 . 1.409(2) ?
C4 C5 . 1.488(2) ?
C5 C6 . 1.393(2) ?
C5 C10 . 1.394(2) ?
C6 C7 . 1.384(2) ?
C6 H6 . 0.950000 ?
C7 C8 . 1.385(2) ?
C7 H7 . 0.950000 ?
C8 C9 . 1.385(2) ?
C8 H8 . 0.950000 ?
C9 C10 . 1.385(2) ?
C9 H9 . 0.950000 ?
C10 H10 . 0.950000 ?
C11 C12 . 1.382(2) ?
C11 H11 . 0.950000 ?
C12 C13 . 1.391(2) ?
C12 H12 . 0.950000 ?
C13 N1 . 1.403(2) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 C1 F1 . . 122.16(15) ?
N1 C1 S1 . . 120.41(13) ?
F1 C1 S1 . . 117.43(13) ?
C3 C2 C13 . . 121.90(14) ?
C3 C2 S1 . . 128.65(12) ?
C13 C2 S1 . . 109.41(12) ?
C2 C3 C4 . . 118.91(14) ?
C2 C3 H3 . . 120.500000 ?
C4 C3 H3 . . 120.500000 ?
C3 C4 C11 . . 119.11(14) ?
C3 C4 C5 . . 119.88(13) ?
C11 C4 C5 . . 120.95(13) ?
C6 C5 C10 . . 118.19(14) ?
C6 C5 C4 . . 121.05(13) ?
C10 C5 C4 . . 120.68(13) ?
C7 C6 C5 . . 120.95(14) ?
C7 C6 H6 . . 119.500000 ?
C5 C6 H6 . . 119.500000 ?
C6 C7 C8 . . 120.44(15) ?
C6 C7 H7 . . 119.800000 ?
C8 C7 H7 . . 119.800000 ?
C7 C8 C9 . . 119.13(15) ?
C7 C8 H8 . . 120.400000 ?
C9 C8 H8 . . 120.400000 ?
C8 C9 C10 . . 120.56(15) ?
C8 C9 H9 . . 119.700000 ?
C10 C9 H9 . . 119.700000 ?
C9 C10 C5 . . 120.73(14) ?
C9 C10 H10 . . 119.600000 ?
C5 C10 H10 . . 119.600000 ?
C12 C11 C4 . . 121.85(15) ?
C12 C11 H11 . . 119.100000 ?
C4 C11 H11 . . 119.100000 ?
C11 C12 C13 . . 118.97(15) ?
C11 C12 H12 . . 120.500000 ?
C13 C12 H12 . . 120.500000 ?
C12 C13 C2 . . 119.25(15) ?
C12 C13 N1 . . 125.29(15) ?
C2 C13 N1 . . 115.44(15) ?
C1 N1 C13 . . 107.76(14) ?
C1 S1 C2 . . 86.97(8) ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C13 C2 C3 C4 . . . . -0.7(2) ?
S1 C2 C3 C4 . . . . 176.57(11) ?
C2 C3 C4 C11 . . . . 1.1(2) ?
C2 C3 C4 C5 . . . . -176.10(13) ?
C3 C4 C5 C6 . . . . -35.8(2) ?
C11 C4 C5 C6 . . . . 147.01(14) ?
C3 C4 C5 C10 . . . . 140.83(14) ?
C11 C4 C5 C10 . . . . -36.3(2) ?
C10 C5 C6 C7 . . . . 0.5(2) ?
C4 C5 C6 C7 . . . . 177.27(14) ?
C5 C6 C7 C8 . . . . -0.8(2) ?
C6 C7 C8 C9 . . . . 0.4(2) ?
C7 C8 C9 C10 . . . . 0.3(2) ?
C8 C9 C10 C5 . . . . -0.6(2) ?
C6 C5 C10 C9 . . . . 0.2(2) ?
C4 C5 C10 C9 . . . . -176.56(13) ?
C3 C4 C11 C12 . . . . -0.7(2) ?
C5 C4 C11 C12 . . . . 176.47(13) ?
C4 C11 C12 C13 . . . . -0.2(2) ?
C11 C12 C13 C2 . . . . 0.6(2) ?
C11 C12 C13 N1 . . . . -178.13(14) ?
C3 C2 C13 C12 . . . . -0.2(2) ?
S1 C2 C13 C12 . . . . -177.92(11) ?
C3 C2 C13 N1 . . . . 178.67(14) ?
S1 C2 C13 N1 . . . . 0.94(16) ?
F1 C1 N1 C13 . . . . 179.95(14) ?
S1 C1 N1 C13 . . . . 0.32(19) ?
C12 C13 N1 C1 . . . . 177.97(15) ?
C2 C13 N1 C1 . . . . -0.81(19) ?
N1 C1 S1 C2 . . . . 0.17(15) ?
F1 C1 S1 C2 . . . . -179.48(13) ?
C3 C2 S1 C1 . . . . -178.13(15) ?
C13 C2 S1 C1 . . . . -0.60(11) ?



