# 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_exp_13273
_audit_block_doi                 10.5517/ccdc.csd.cc2gy78y
_database_code_depnum_ccdc_archive 'CCDC 2292210'
loop_
_audit_author_name
_audit_author_address
'Yao Zhou'
;Hubei Normal University
China
;
_audit_update_record             
;
2023-09-01 deposited with the CCDC.	2024-02-05 downloaded from the CCDC.
;
_audit_creation_date             2023-05-31
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H10 F N O2 S'
_chemical_formula_sum            'C11 H10 F N O2 S'
_chemical_formula_weight         239.26
_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'
N N 0.0061 0.0033 '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                   7.7589(11)
_cell_length_b                   11.6408(17)
_cell_length_c                   12.3519(15)
_cell_angle_alpha                90
_cell_angle_beta                 107.201(15)
_cell_angle_gamma                90
_cell_volume                     1065.7(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1190
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      26.4730
_cell_measurement_theta_min      4.0960
_shelx_estimated_absorpt_T_max   0.956
_shelx_estimated_absorpt_T_min   0.948
_exptl_absorpt_coefficient_mu    0.301
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48104
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.491
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_unetI/netI     0.0691
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.838
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4892
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.838
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.175
_diffrn_reflns_theta_min         3.453
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0606
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.838
_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  49.00   1.00   10.50    --  -16.28  57.00 -30.00   38
  2  ω    -41.00  45.00   1.00   10.50    --   15.49 -19.00 150.00   86
  3  ω    -48.00  15.00   1.00   10.50    --   15.49 -57.00 120.00   63
  4  ω    -65.00 -37.00   1.00   10.50    --  -16.28 149.00 -34.00   28
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0714416000
_diffrn_orient_matrix_UB_12      -0.0353584000
_diffrn_orient_matrix_UB_13      -0.0320271000
_diffrn_orient_matrix_UB_21      -0.0184863000
_diffrn_orient_matrix_UB_22      -0.0171646000
_diffrn_orient_matrix_UB_23      0.0505232000
_diffrn_orient_matrix_UB_31      -0.0609355000
_diffrn_orient_matrix_UB_32      0.0465907000
_diffrn_orient_matrix_UB_33      -0.0056921000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1520
_reflns_number_total             2417
_reflns_odcompleteness_completeness 99.52
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2008)'
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       0.0087(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2417
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1042
_refine_ls_R_factor_gt           0.0579
_refine_ls_restrained_S_all      1.043
_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)+(0.0394P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0966
_refine_ls_wR_factor_ref         0.1138
_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:
 C00I(H00I)
2.b Secondary CH2 refined with riding coordinates:
 C00E(H00A,H00B), C00T(H00C,H00D), C00W(H00E,H00F)
2.c Aromatic/amide H refined with riding coordinates:
 C00O(H00O), C00Q(H00Q), C00U(H00U)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
S001 S 0.30654(9) 0.41866(7) 0.25924(5) 0.0470(2) Uani 1 1 d . . . . .
F003 F 0.1968(2) 0.74511(16) 0.59667(15) 0.0785(6) Uani 1 1 d . . . . .
O004 O 0.2825(2) 0.31999(17) 0.59469(13) 0.0499(5) Uani 1 1 d . . . . .
O009 O 0.2639(3) -0.00515(18) 0.34569(19) 0.0741(7) Uani 1 1 d . . . . .
N008 N 0.2437(3) 0.27050(19) 0.41090(15) 0.0375(5) Uani 1 1 d . . . . .
C00B C 0.2449(3) 0.4737(2) 0.46306(19) 0.0326(6) Uani 1 1 d . . . . .
C00E C 0.1714(3) 0.3066(2) 0.29288(18) 0.0402(7) Uani 1 1 d . . . . .
H00A H 0.048824 0.333945 0.279529 0.048 Uiso 1 1 calc R U . . .
H00B H 0.168277 0.241261 0.243580 0.048 Uiso 1 1 calc R U . . .
C00F C 0.2783(3) 0.5146(2) 0.36377(19) 0.0352(6) Uani 1 1 d . . . . .
C00I C 0.2884(3) 0.1512(2) 0.4380(2) 0.0397(6) Uani 1 1 d . . . . .
H00I H 0.345378 0.141972 0.519678 0.048 Uiso 1 1 calc R U . . .
C00K C 0.2556(3) 0.3492(2) 0.49500(19) 0.0349(6) Uani 1 1 d . . . . .
C00L C 0.2260(3) 0.6676(3) 0.5200(2) 0.0489(7) Uani 1 1 d . . . . .
C00O C 0.2891(3) 0.6327(3) 0.3474(2) 0.0470(7) Uani 1 1 d . . . . .
H00O H 0.314064 0.659477 0.282673 0.056 Uiso 1 1 calc R U . . .
C00Q C 0.2193(3) 0.5532(3) 0.5421(2) 0.0408(7) Uani 1 1 d . . . . .
H00Q H 0.198193 0.528275 0.608618 0.049 Uiso 1 1 calc R U . . .
C00T C 0.3950(4) 0.0865(2) 0.3715(2) 0.0495(7) Uani 1 1 d . . . . .
H00C H 0.403596 0.127502 0.304960 0.059 Uiso 1 1 calc R U . . .
H00D H 0.513444 0.062078 0.417822 0.059 Uiso 1 1 calc R U . . .
C00U C 0.2633(3) 0.7104(3) 0.4254(2) 0.0527(8) Uani 1 1 d . . . . .
H00U H 0.270848 0.789072 0.414489 0.063 Uiso 1 1 calc R U . . .
C00W C 0.1455(4) 0.0585(3) 0.3940(3) 0.0653(9) Uani 1 1 d . . . . .
H00E H 0.114096 0.017375 0.453867 0.078 Uiso 1 1 calc R U . . .
H00F H 0.037915 0.086543 0.337963 0.078 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
S001 C00E 1.798(3) . ?
S001 C00F 1.769(3) . ?
F003 C00L 1.374(3) . ?
O004 C00K 1.234(3) . ?
O009 C00T 1.443(3) . ?
O009 C00W 1.440(3) . ?
N008 C00E 1.460(3) . ?
N008 C00I 1.446(3) . ?
N008 C00K 1.367(3) . ?
C00B C00F 1.410(3) . ?
C00B C00K 1.498(4) . ?
C00B C00Q 1.402(3) . ?
C00E H00A 0.9700 . ?
C00E H00B 0.9700 . ?
C00F C00O 1.396(4) . ?
C00I H00I 0.9800 . ?
C00I C00T 1.526(3) . ?
C00I C00W 1.527(4) . ?
C00L C00Q 1.365(4) . ?
C00L C00U 1.378(4) . ?
C00O H00O 0.9300 . ?
C00O C00U 1.378(4) . ?
C00Q H00Q 0.9300 . ?
C00T H00C 0.9700 . ?
C00T H00D 0.9700 . ?
C00U H00U 0.9300 . ?
C00W H00E 0.9700 . ?
C00W H00F 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
C00F S001 C00E 94.76(12) . . ?
C00W O009 C00T 91.3(2) . . ?
C00I N008 C00E 120.2(2) . . ?
C00K N008 C00E 119.0(2) . . ?
C00K N008 C00I 120.61(19) . . ?
C00F C00B C00K 123.1(2) . . ?
C00Q C00B C00F 118.9(2) . . ?
C00Q C00B C00K 117.6(2) . . ?
S001 C00E H00A 109.4 . . ?
S001 C00E H00B 109.4 . . ?
N008 C00E S001 111.19(16) . . ?
N008 C00E H00A 109.4 . . ?
N008 C00E H00B 109.4 . . ?
H00A C00E H00B 108.0 . . ?
C00B C00F S001 121.0(2) . . ?
C00O C00F S001 119.36(19) . . ?
C00O C00F C00B 119.6(2) . . ?
N008 C00I H00I 110.4 . . ?
N008 C00I C00T 118.7(2) . . ?
N008 C00I C00W 119.8(2) . . ?
C00T C00I H00I 110.4 . . ?
C00T C00I C00W 84.9(2) . . ?
C00W C00I H00I 110.4 . . ?
O004 C00K N008 121.8(3) . . ?
O004 C00K C00B 120.6(2) . . ?
N008 C00K C00B 117.5(2) . . ?
F003 C00L C00U 117.8(3) . . ?
C00Q C00L F003 118.6(3) . . ?
C00Q C00L C00U 123.6(3) . . ?
C00F C00O H00O 119.4 . . ?
C00U C00O C00F 121.2(3) . . ?
C00U C00O H00O 119.4 . . ?
C00B C00Q H00Q 120.5 . . ?
C00L C00Q C00B 118.9(2) . . ?
C00L C00Q H00Q 120.5 . . ?
O009 C00T C00I 91.42(19) . . ?
O009 C00T H00C 113.4 . . ?
O009 C00T H00D 113.4 . . ?
C00I C00T H00C 113.4 . . ?
C00I C00T H00D 113.4 . . ?
H00C C00T H00D 110.7 . . ?
C00L C00U C00O 117.8(3) . . ?
C00L C00U H00U 121.1 . . ?
C00O C00U H00U 121.1 . . ?
O009 C00W C00I 91.5(2) . . ?
O009 C00W H00E 113.4 . . ?
O009 C00W H00F 113.4 . . ?
C00I C00W H00E 113.4 . . ?
C00I C00W H00F 113.4 . . ?
H00E C00W H00F 110.7 . . ?

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
S001 C00F C00O C00U 178.34(18) . . . . ?
F003 C00L C00Q C00B 178.58(19) . . . . ?
F003 C00L C00U C00O -178.8(2) . . . . ?
N008 C00I C00T O009 -128.1(2) . . . . ?
N008 C00I C00W O009 127.1(2) . . . . ?
C00B C00F C00O C00U -1.6(4) . . . . ?
C00E S001 C00F C00B 27.21(19) . . . . ?
C00E S001 C00F C00O -152.7(2) . . . . ?
C00E N008 C00I C00T 46.0(3) . . . . ?
C00E N008 C00I C00W -55.4(3) . . . . ?
C00E N008 C00K O004 166.0(2) . . . . ?
C00E N008 C00K C00B -17.3(3) . . . . ?
C00F S001 C00E N008 -58.69(18) . . . . ?
C00F C00B C00K O004 156.8(2) . . . . ?
C00F C00B C00K N008 -19.9(3) . . . . ?
C00F C00B C00Q C00L 0.6(3) . . . . ?
C00F C00O C00U C00L -0.2(4) . . . . ?
C00I N008 C00E S001 -124.2(2) . . . . ?
C00I N008 C00K O004 -9.1(3) . . . . ?
C00I N008 C00K C00B 167.65(19) . . . . ?
C00K N008 C00E S001 60.7(2) . . . . ?
C00K N008 C00I C00T -139.0(2) . . . . ?
C00K N008 C00I C00W 119.6(3) . . . . ?
C00K C00B C00F S001 8.5(3) . . . . ?
C00K C00B C00F C00O -171.6(2) . . . . ?
C00K C00B C00Q C00L 173.9(2) . . . . ?
C00Q C00B C00F S001 -178.54(17) . . . . ?
C00Q C00B C00F C00O 1.4(3) . . . . ?
C00Q C00B C00K O004 -16.2(3) . . . . ?
C00Q C00B C00K N008 167.06(19) . . . . ?
C00Q C00L C00U C00O 2.3(4) . . . . ?
C00T O009 C00W C00I -7.2(2) . . . . ?
C00T C00I C00W O009 6.8(2) . . . . ?
C00U C00L C00Q C00B -2.5(4) . . . . ?
C00W O009 C00T C00I 7.2(2) . . . . ?
C00W C00I C00T O009 -6.8(2) . . . . ?

_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 2.217
_oxdiff_exptl_absorpt_empirical_full_min 0.543
