# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2021

####################################################################### 
# 
# 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_cxy1483_0m
_database_code_depnum_ccdc_archive 'CCDC 2060368'
loop_
_audit_author_name
_audit_author_address
'Pengfei Li'
;Southern University of Science and Technology
China
;
_audit_update_record             
;
2021-02-02 deposited with the CCDC.	2021-04-25 downloaded from the CCDC.
;
_audit_creation_date             2020-10-20
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H14 F3 N O S'
_chemical_formula_sum            'C17 H14 F3 N O S'
_chemical_formula_weight         337.35
_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   8.9035(15)
_cell_length_b                   9.1118(17)
_cell_length_c                   20.094(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1630.1(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9986
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      2.45
_shelx_estimated_absorpt_T_max   0.968
_shelx_estimated_absorpt_T_min   0.932
_exptl_absorpt_coefficient_mu    0.231
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6163
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1210 before and 0.0739 after correction.
The Ratio of minimum to maximum transmission is 0.8266.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0760
_diffrn_reflns_av_unetI/netI     0.0439
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            27976
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.813
_diffrn_reflns_theta_min         2.454
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker PHOTON 100 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker CMOS area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.740
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                3259
_reflns_number_total             3831
_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         0.235
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 
;
 Flack x determined using 1216 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3831
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0358
_refine_ls_restrained_S_all      1.047
_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)+(0.0390P)²+0.3638P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0802
_refine_ls_wR_factor_ref         0.0863
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C2(H2), C15(H15), C16(H16), C17(H17)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_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 0.41664(8) 0.61202(7) 0.34419(3) 0.02596(16) Uani 1 1 d . . . . .
F1 F 0.8700(2) 0.2935(2) 0.25300(8) 0.0448(5) Uani 1 1 d . . . . .
F2 F 1.03293(19) 0.4565(2) 0.27844(8) 0.0426(5) Uani 1 1 d . . . . .
F3 F 0.8287(2) 0.5196(2) 0.23011(8) 0.0432(5) Uani 1 1 d . . . . .
O1 O 0.4475(2) 0.6217(2) 0.47477(9) 0.0276(4) Uani 1 1 d . . . . .
N1 N 0.9951(3) 0.1886(3) 0.45566(12) 0.0307(6) Uani 1 1 d . . . . .
H1 H 1.048473 0.109462 0.464215 0.037 Uiso 1 1 calc R U . . .
C1 C 0.8794(3) 0.3882(3) 0.60738(13) 0.0263(6) Uani 1 1 d . . . . .
H1A H 0.882366 0.386704 0.654636 0.032 Uiso 1 1 calc R U . . .
C2 C 0.9481(3) 0.2774(3) 0.57199(14) 0.0276(6) Uani 1 1 d . . . . .
H2 H 1.001311 0.200959 0.593846 0.033 Uiso 1 1 calc R U . . .
C3 C 0.9365(3) 0.2821(3) 0.50282(13) 0.0234(5) Uani 1 1 d . . . . .
C4 C 0.8593(3) 0.3944(3) 0.46884(12) 0.0190(5) Uani 1 1 d . . . . .
C5 C 0.8735(3) 0.3634(3) 0.39871(12) 0.0201(5) Uani 1 1 d . . . . .
C6 C 0.8144(3) 0.4509(3) 0.34369(13) 0.0209(5) Uani 1 1 d . . . . .
C7 C 0.7089(3) 0.5506(3) 0.34917(12) 0.0220(5) Uani 1 1 d . . . . .
C8 C 0.6105(3) 0.6554(3) 0.35617(11) 0.0220(5) Uani 1 1 d . . . . .
C9 C 0.3597(3) 0.6054(3) 0.42970(13) 0.0245(5) Uani 1 1 d . . . . .
C10 C 0.1954(3) 0.5754(4) 0.43839(16) 0.0380(7) Uani 1 1 d . . . . .
H10A H 0.182093 0.486351 0.465121 0.057 Uiso 1 1 calc R U . . .
H10B H 0.148714 0.561525 0.394677 0.057 Uiso 1 1 calc R U . . .
H10C H 0.148013 0.658565 0.461060 0.057 Uiso 1 1 calc R U . . .
C11 C 0.6479(3) 0.8105(3) 0.37173(13) 0.0238(6) Uani 1 1 d . . . . .
H11 H 0.585440 0.857302 0.407227 0.029 Uiso 1 1 calc R U . . .
C12 C 0.8074(3) 0.8620(3) 0.36769(14) 0.0316(6) Uani 1 1 d . . . . .
H12A H 0.841381 0.935297 0.400783 0.038 Uiso 1 1 calc R U . . .
H12B H 0.884649 0.789650 0.354272 0.038 Uiso 1 1 calc R U . . .
C13 C 0.6976(3) 0.9109(3) 0.31617(15) 0.0327(7) Uani 1 1 d . . . . .
H13A H 0.706784 0.868489 0.270979 0.039 Uiso 1 1 calc R U . . .
H13B H 0.663494 1.014214 0.317515 0.039 Uiso 1 1 calc R U . . .
C14 C 0.8856(3) 0.4305(3) 0.27633(13) 0.0289(6) Uani 1 1 d . . . . .
C15 C 0.8051(3) 0.5031(3) 0.57469(13) 0.0244(6) Uani 1 1 d . . . . .
H15 H 0.760221 0.579046 0.600291 0.029 Uiso 1 1 calc R U . . .
C16 C 0.7956(3) 0.5086(3) 0.50618(13) 0.0211(5) Uani 1 1 d . . . . .
H16 H 0.746831 0.588255 0.484694 0.025 Uiso 1 1 calc R U . . .
C17 C 0.9578(3) 0.2375(3) 0.39360(13) 0.0264(6) Uani 1 1 d . . . . .
H17 H 0.985803 0.191441 0.353037 0.032 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 C8 1.787(3) . ?
S1 C9 1.793(3) . ?
F1 C14 1.341(3) . ?
F2 C14 1.333(3) . ?
F3 C14 1.334(3) . ?
O1 C9 1.205(3) . ?
N1 H1 0.8800 . ?
N1 C3 1.377(3) . ?
N1 C17 1.365(3) . ?
C1 H1A 0.9500 . ?
C1 C2 1.378(4) . ?
C1 C15 1.402(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.395(4) . ?
C3 C4 1.409(3) . ?
C4 C5 1.443(3) . ?
C4 C16 1.402(3) . ?
C5 C6 1.461(3) . ?
C5 C17 1.375(3) . ?
C6 C7 1.311(3) . ?
C6 C14 1.506(4) . ?
C7 C8 1.303(4) . ?
C8 C11 1.485(4) . ?
C9 C10 1.498(4) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11 1.0000 . ?
C11 C12 1.498(4) . ?
C11 C13 1.510(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.492(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C15 H15 0.9500 . ?
C15 C16 1.380(4) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?

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
C8 S1 C9 98.72(12) . . ?
C3 N1 H1 125.2 . . ?
C17 N1 H1 125.2 . . ?
C17 N1 C3 109.5(2) . . ?
C2 C1 H1A 119.5 . . ?
C2 C1 C15 121.0(2) . . ?
C15 C1 H1A 119.5 . . ?
C1 C2 H2 121.3 . . ?
C1 C2 C3 117.3(2) . . ?
C3 C2 H2 121.3 . . ?
N1 C3 C2 129.7(2) . . ?
N1 C3 C4 107.5(2) . . ?
C2 C3 C4 122.8(2) . . ?
C3 C4 C5 106.7(2) . . ?
C16 C4 C3 118.5(2) . . ?
C16 C4 C5 134.7(2) . . ?
C4 C5 C6 126.9(2) . . ?
C17 C5 C4 106.5(2) . . ?
C17 C5 C6 126.6(2) . . ?
C5 C6 C14 117.4(2) . . ?
C7 C6 C5 124.9(2) . . ?
C7 C6 C14 117.6(2) . . ?
C8 C7 C6 176.3(3) . . ?
C7 C8 S1 118.2(2) . . ?
C7 C8 C11 124.7(2) . . ?
C11 C8 S1 117.07(19) . . ?
O1 C9 S1 122.2(2) . . ?
O1 C9 C10 124.6(3) . . ?
C10 C9 S1 113.2(2) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 H11 115.6 . . ?
C8 C11 C12 119.9(2) . . ?
C8 C11 C13 119.1(2) . . ?
C12 C11 H11 115.6 . . ?
C12 C11 C13 59.47(19) . . ?
C13 C11 H11 115.6 . . ?
C11 C12 H12A 117.7 . . ?
C11 C12 H12B 117.7 . . ?
H12A C12 H12B 114.8 . . ?
C13 C12 C11 60.66(19) . . ?
C13 C12 H12A 117.7 . . ?
C13 C12 H12B 117.7 . . ?
C11 C13 H13A 117.8 . . ?
C11 C13 H13B 117.8 . . ?
C12 C13 C11 59.88(19) . . ?
C12 C13 H13A 117.8 . . ?
C12 C13 H13B 117.8 . . ?
H13A C13 H13B 114.9 . . ?
F1 C14 C6 112.6(2) . . ?
F2 C14 F1 106.2(2) . . ?
F2 C14 F3 106.8(2) . . ?
F2 C14 C6 111.3(2) . . ?
F3 C14 F1 106.5(2) . . ?
F3 C14 C6 113.0(2) . . ?
C1 C15 H15 119.2 . . ?
C16 C15 C1 121.5(2) . . ?
C16 C15 H15 119.2 . . ?
C4 C16 H16 120.6 . . ?
C15 C16 C4 118.8(2) . . ?
C15 C16 H16 120.6 . . ?
N1 C17 C5 109.7(2) . . ?
N1 C17 H17 125.1 . . ?
C5 C17 H17 125.1 . . ?

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 C8 C11 C12 -166.61(19) . . . . ?
S1 C8 C11 C13 -97.1(3) . . . . ?
N1 C3 C4 C5 0.4(3) . . . . ?
N1 C3 C4 C16 -176.7(2) . . . . ?
C1 C2 C3 N1 178.9(3) . . . . ?
C1 C2 C3 C4 0.4(4) . . . . ?
C1 C15 C16 C4 1.4(4) . . . . ?
C2 C1 C15 C16 1.1(4) . . . . ?
C2 C3 C4 C5 179.1(2) . . . . ?
C2 C3 C4 C16 2.1(4) . . . . ?
C3 N1 C17 C5 -0.3(3) . . . . ?
C3 C4 C5 C6 -178.7(2) . . . . ?
C3 C4 C5 C17 -0.5(3) . . . . ?
C3 C4 C16 C15 -2.9(4) . . . . ?
C4 C5 C6 C7 -17.8(4) . . . . ?
C4 C5 C6 C14 158.9(2) . . . . ?
C4 C5 C17 N1 0.5(3) . . . . ?
C5 C4 C16 C15 -179.0(3) . . . . ?
C5 C6 C14 F1 62.1(3) . . . . ?
C5 C6 C14 F2 -57.1(3) . . . . ?
C5 C6 C14 F3 -177.2(2) . . . . ?
C6 C5 C17 N1 178.6(2) . . . . ?
C7 C6 C14 F1 -121.0(3) . . . . ?
C7 C6 C14 F2 119.8(3) . . . . ?
C7 C6 C14 F3 -0.3(3) . . . . ?
C7 C8 C11 C12 11.7(4) . . . . ?
C7 C8 C11 C13 81.2(3) . . . . ?
C8 S1 C9 O1 -3.0(2) . . . . ?
C8 S1 C9 C10 178.0(2) . . . . ?
C8 C11 C12 C13 108.2(3) . . . . ?
C8 C11 C13 C12 -109.6(3) . . . . ?
C9 S1 C8 C7 103.1(2) . . . . ?
C9 S1 C8 C11 -78.5(2) . . . . ?
C15 C1 C2 C3 -2.0(4) . . . . ?
C16 C4 C5 C6 -2.3(4) . . . . ?
C16 C4 C5 C17 175.9(3) . . . . ?
C17 N1 C3 C2 -178.7(3) . . . . ?
C17 N1 C3 C4 -0.1(3) . . . . ?
C17 C5 C6 C7 164.4(3) . . . . ?
C17 C5 C6 C14 -18.9(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
