# 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_2022031101_0m
_database_code_depnum_ccdc_archive 'CCDC 2235492'
loop_
_audit_author_name
_audit_author_address
'Wen Yang'
;Hunan University
China
;
_audit_update_record             
;
2023-01-11 deposited with the CCDC.	2023-06-05 downloaded from the CCDC.
;
_audit_creation_date             2022-03-12
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.07.19 svn.r715e62df for OlexSys, GUI svn.r6380)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H12 F3 N O2 S'
_chemical_formula_sum            'C17 H12 F3 N O2 S'
_chemical_formula_weight         351.34
_chemical_absolute_configuration ad
_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           5
_space_group_name_H-M_alt        'C 1 2 1'
_space_group_name_Hall           'C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   25.755(3)
_cell_length_b                   6.9641(8)
_cell_length_c                   8.7584(10)
_cell_angle_alpha                90
_cell_angle_beta                 94.153(4)
_cell_angle_gamma                90
_cell_volume                     1566.8(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9954
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      28.34
_cell_measurement_theta_min      2.33
_shelx_estimated_absorpt_T_max   0.945
_shelx_estimated_absorpt_T_min   0.918
_exptl_absorpt_coefficient_mu    0.249
_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            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.23
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10899
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.338
_diffrn_reflns_theta_min         2.331
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_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
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.848
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                3820
_reflns_number_total             3882
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details 
;
 Flack x determined using 1726 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3882
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0279
_refine_ls_R_factor_gt           0.0275
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0337P)²+0.4207P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0699
_refine_ls_wR_factor_ref         0.0702
_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 Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1A), C2(H2), C9(H9), C10(H10), C11(H11), C13(H13), C14(H14), C16(H16),
 C17(H17)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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 0.33188(2) 0.84708(6) 0.81823(4) 0.02804(11) Uani 1 1 d . . . . .
F1 F 0.33398(5) 0.2821(2) 1.10734(14) 0.0433(3) Uani 1 1 d . . . . .
F2 F 0.29793(4) 0.27809(17) 0.87799(13) 0.0323(2) Uani 1 1 d . . . . .
F3 F 0.28581(5) 0.51790(19) 1.02579(14) 0.0393(3) Uani 1 1 d . . . . .
O1 O 0.38862(6) 0.6058(2) 1.04986(14) 0.0312(3) Uani 1 1 d . . . . .
O2 O 0.46736(6) 0.5882(2) 0.84853(18) 0.0394(3) Uani 1 1 d . . . . .
N1 N 0.35159(6) 0.5538(2) 0.64823(16) 0.0228(3) Uani 1 1 d . . . . .
C1 C 0.29589(7) 1.0134(3) 0.3801(2) 0.0319(4) Uani 1 1 d . . . . .
H1A H 0.282850 1.116419 0.321703 0.038 Uiso 1 1 calc R U . . .
C2 C 0.30121(7) 1.0298(3) 0.5378(2) 0.0300(4) Uani 1 1 d . . . . .
H2 H 0.292243 1.142487 0.586412 0.036 Uiso 1 1 calc R U . . .
C3 C 0.32042(6) 0.8721(3) 0.62116(18) 0.0232(3) Uani 1 1 d . . . . .
C4 C 0.35236(6) 0.6121(2) 0.78812(18) 0.0217(3) Uani 1 1 d . . . . .
C5 C 0.36937(7) 0.4894(3) 0.92619(18) 0.0239(3) Uani 1 1 d . . . . .
C6 C 0.40771(6) 0.3343(3) 0.88404(18) 0.0255(3) Uani 1 1 d . . . . .
H6A H 0.415541 0.251829 0.971946 0.031 Uiso 1 1 calc R U . . .
H6B H 0.391628 0.255928 0.802144 0.031 Uiso 1 1 calc R U . . .
C7 C 0.45793(7) 0.4181(3) 0.8333(2) 0.0272(3) Uani 1 1 d . . . . .
C8 C 0.49502(7) 0.2854(3) 0.7645(2) 0.0282(4) Uani 1 1 d . . . . .
C9 C 0.53480(7) 0.3627(3) 0.6834(2) 0.0317(4) Uani 1 1 d . . . . .
H9 H 0.538321 0.495285 0.676510 0.038 Uiso 1 1 calc R U . . .
C10 C 0.56907(8) 0.2441(3) 0.6132(3) 0.0385(5) Uani 1 1 d . . . . .
H10 H 0.594844 0.296209 0.556683 0.046 Uiso 1 1 calc R U . . .
C11 C 0.56454(9) 0.0480(4) 0.6280(4) 0.0520(6) Uani 1 1 d . . . . .
H11 H 0.587425 -0.032357 0.581071 0.062 Uiso 1 1 calc R U . . .
C12 C 0.33355(6) 0.6999(2) 0.54940(18) 0.0217(3) Uani 1 1 d . . . . .
C13 C 0.32848(7) 0.6871(3) 0.3898(2) 0.0284(3) Uani 1 1 d . . . . .
H13 H 0.337505 0.575035 0.340359 0.034 Uiso 1 1 calc R U . . .
C14 C 0.30981(7) 0.8443(4) 0.30700(18) 0.0319(4) Uani 1 1 d . . . . .
H14 H 0.306406 0.837711 0.200691 0.038 Uiso 1 1 calc R U . . .
C15 C 0.32114(7) 0.3909(3) 0.9851(2) 0.0283(4) Uani 1 1 d . . . . .
C16 C 0.52618(10) -0.0309(3) 0.7123(4) 0.0595(8) Uani 1 1 d . . . . .
H16 H 0.524152 -0.163390 0.724031 0.071 Uiso 1 1 calc R U . . .
C17 C 0.49090(8) 0.0875(3) 0.7789(3) 0.0424(5) Uani 1 1 d . . . . .
H17 H 0.464600 0.034618 0.832957 0.051 Uiso 1 1 calc R U . . .
H1 H 0.4175(11) 0.635(4) 1.033(3) 0.044(8) Uiso 1 1 d . . . . .


_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 C3 1.7387(17) . ?
S1 C4 1.7452(17) . ?
F1 C15 1.334(2) . ?
F2 C15 1.332(2) . ?
F3 C15 1.336(2) . ?
O1 C5 1.414(2) . ?
O1 H1 0.80(3) . ?
O2 C7 1.215(2) . ?
N1 C4 1.290(2) . ?
N1 C12 1.393(2) . ?
C1 H1A 0.9300 . ?
C1 C2 1.382(3) . ?
C1 C14 1.400(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.390(2) . ?
C3 C12 1.407(2) . ?
C4 C5 1.519(2) . ?
C5 C6 1.527(2) . ?
C5 C15 1.540(2) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.515(2) . ?
C7 C8 1.488(3) . ?
C8 C9 1.396(3) . ?
C8 C17 1.389(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.385(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.377(4) . ?
C11 H11 0.9300 . ?
C11 C16 1.389(4) . ?
C12 C13 1.398(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.380(3) . ?
C14 H14 0.9300 . ?
C16 H16 0.9300 . ?
C16 C17 1.387(3) . ?
C17 H17 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
C3 S1 C4 88.59(8) . . ?
C5 O1 H1 107(2) . . ?
C4 N1 C12 109.98(14) . . ?
C2 C1 H1A 119.4 . . ?
C2 C1 C14 121.11(17) . . ?
C14 C1 H1A 119.4 . . ?
C1 C2 H2 121.1 . . ?
C1 C2 C3 117.72(17) . . ?
C3 C2 H2 121.1 . . ?
C2 C3 S1 128.98(14) . . ?
C2 C3 C12 121.80(15) . . ?
C12 C3 S1 109.22(12) . . ?
N1 C4 S1 117.05(13) . . ?
N1 C4 C5 124.25(15) . . ?
C5 C4 S1 118.69(12) . . ?
O1 C5 C4 110.63(14) . . ?
O1 C5 C6 113.20(14) . . ?
O1 C5 C15 104.20(14) . . ?
C4 C5 C6 111.09(14) . . ?
C4 C5 C15 108.90(14) . . ?
C6 C5 C15 108.50(14) . . ?
C5 C6 H6A 109.1 . . ?
C5 C6 H6B 109.1 . . ?
H6A C6 H6B 107.9 . . ?
C7 C6 C5 112.29(15) . . ?
C7 C6 H6A 109.1 . . ?
C7 C6 H6B 109.1 . . ?
O2 C7 C6 120.79(17) . . ?
O2 C7 C8 121.41(17) . . ?
C8 C7 C6 117.80(16) . . ?
C9 C8 C7 118.85(18) . . ?
C17 C8 C7 121.62(18) . . ?
C17 C8 C9 119.52(19) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 C8 120.7(2) . . ?
C10 C9 H9 119.7 . . ?
C9 C10 H10 120.4 . . ?
C11 C10 C9 119.2(2) . . ?
C11 C10 H10 120.4 . . ?
C10 C11 H11 119.6 . . ?
C10 C11 C16 120.7(2) . . ?
C16 C11 H11 119.6 . . ?
N1 C12 C3 115.16(14) . . ?
N1 C12 C13 125.29(16) . . ?
C13 C12 C3 119.55(16) . . ?
C12 C13 H13 120.7 . . ?
C14 C13 C12 118.60(17) . . ?
C14 C13 H13 120.7 . . ?
C1 C14 H14 119.4 . . ?
C13 C14 C1 121.20(16) . . ?
C13 C14 H14 119.4 . . ?
F1 C15 F3 107.21(15) . . ?
F1 C15 C5 111.26(15) . . ?
F2 C15 F1 107.64(15) . . ?
F2 C15 F3 107.39(15) . . ?
F2 C15 C5 111.02(14) . . ?
F3 C15 C5 112.09(14) . . ?
C11 C16 H16 120.0 . . ?
C17 C16 C11 120.1(2) . . ?
C17 C16 H16 120.0 . . ?
C8 C17 H17 120.2 . . ?
C16 C17 C8 119.7(2) . . ?
C16 C17 H17 120.2 . . ?

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
S1 C3 C12 N1 0.50(18) . . . . ?
S1 C3 C12 C13 -178.79(13) . . . . ?
S1 C4 C5 O1 -27.31(19) . . . . ?
S1 C4 C5 C6 -153.91(12) . . . . ?
S1 C4 C5 C15 86.64(16) . . . . ?
O1 C5 C6 C7 -61.54(18) . . . . ?
O1 C5 C15 F1 -61.48(18) . . . . ?
O1 C5 C15 F2 178.66(14) . . . . ?
O1 C5 C15 F3 58.56(18) . . . . ?
O2 C7 C8 C9 -15.5(3) . . . . ?
O2 C7 C8 C17 164.6(2) . . . . ?
N1 C4 C5 O1 153.23(16) . . . . ?
N1 C4 C5 C6 26.6(2) . . . . ?
N1 C4 C5 C15 -92.82(19) . . . . ?
N1 C12 C13 C14 179.78(16) . . . . ?
C1 C2 C3 S1 179.67(15) . . . . ?
C1 C2 C3 C12 -0.8(3) . . . . ?
C2 C1 C14 C13 1.1(3) . . . . ?
C2 C3 C12 N1 -179.13(16) . . . . ?
C2 C3 C12 C13 1.6(2) . . . . ?
C3 S1 C4 N1 0.35(14) . . . . ?
C3 S1 C4 C5 -179.15(14) . . . . ?
C3 C12 C13 C14 -1.0(2) . . . . ?
C4 S1 C3 C2 179.15(17) . . . . ?
C4 S1 C3 C12 -0.44(12) . . . . ?
C4 N1 C12 C3 -0.3(2) . . . . ?
C4 N1 C12 C13 178.99(16) . . . . ?
C4 C5 C6 C7 63.63(18) . . . . ?
C4 C5 C15 F1 -179.57(15) . . . . ?
C4 C5 C15 F2 60.58(18) . . . . ?
C4 C5 C15 F3 -59.52(18) . . . . ?
C5 C6 C7 O2 9.9(2) . . . . ?
C5 C6 C7 C8 -170.03(15) . . . . ?
C6 C5 C15 F1 59.39(18) . . . . ?
C6 C5 C15 F2 -60.46(17) . . . . ?
C6 C5 C15 F3 179.44(14) . . . . ?
C6 C7 C8 C9 164.44(16) . . . . ?
C6 C7 C8 C17 -15.4(3) . . . . ?
C7 C8 C9 C10 -177.79(18) . . . . ?
C7 C8 C17 C16 179.7(2) . . . . ?
C8 C9 C10 C11 -2.0(3) . . . . ?
C9 C8 C17 C16 -0.2(4) . . . . ?
C9 C10 C11 C16 0.0(4) . . . . ?
C10 C11 C16 C17 1.9(5) . . . . ?
C11 C16 C17 C8 -1.8(5) . . . . ?
C12 N1 C4 S1 -0.12(18) . . . . ?
C12 N1 C4 C5 179.35(15) . . . . ?
C12 C13 C14 C1 -0.3(3) . . . . ?
C14 C1 C2 C3 -0.5(3) . . . . ?
C15 C5 C6 C7 -176.69(14) . . . . ?
C17 C8 C9 C10 2.1(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
