# 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_ww_a
_database_code_depnum_ccdc_archive 'CCDC 2246226'
loop_
_audit_author_name
_audit_author_address
'Wen Yang'
;Hunan University
China
;
_audit_update_record             
;
2023-03-04 deposited with the CCDC.	2023-05-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H13 F3 N2 O S'
_chemical_formula_weight         374.37

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.929(3)
_cell_length_b                   9.985(3)
_cell_length_c                   10.178(3)
_cell_angle_alpha                101.361(6)
_cell_angle_beta                 92.022(7)
_cell_angle_gamma                108.738(7)
_cell_volume                     837.7(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_F_000             384
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.235
_shelx_estimated_absorpt_T_min   0.950
_shelx_estimated_absorpt_T_max   0.972
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18847
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.208
_diffrn_reflns_theta_max         28.583
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4194
_reflns_number_gt                3548
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0759P)²+2.2170P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4194
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1064
_refine_ls_R_factor_gt           0.0932
_refine_ls_wR_factor_ref         0.2310
_refine_ls_wR_factor_gt          0.2208
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 0.4332(4) 0.8150(5) 0.1713(3) 0.0445(8) Uani 1 1 d . . . . .
C2 C 0.6949(4) 0.8982(4) 0.2058(4) 0.0417(8) Uani 1 1 d . . . . .
C3 C 0.6632(4) 0.9880(3) 0.3161(3) 0.0376(7) Uani 1 1 d . . . . .
C4 C 0.7869(5) 1.0888(4) 0.4081(4) 0.0531(10) Uani 1 1 d . . . . .
H4 H 0.765598 1.149847 0.483926 0.064 Uiso 1 1 calc R U . . .
C5 C 0.9397(5) 1.0972(5) 0.3862(5) 0.0599(11) Uani 1 1 d . . . . .
H5 H 1.025145 1.164813 0.448166 0.072 Uiso 1 1 calc R U . . .
C6 C 0.9725(5) 1.0097(5) 0.2762(5) 0.0580(11) Uani 1 1 d . . . . .
H6 H 1.079883 1.019033 0.262976 0.070 Uiso 1 1 calc R U . . .
C7 C 0.8518(4) 0.9093(5) 0.1854(5) 0.0560(11) Uani 1 1 d . . . . .
H7 H 0.874792 0.848657 0.110261 0.067 Uiso 1 1 calc R U . . .
C8 C 0.2271(6) 0.7870(12) -0.0099(6) 0.109(3) Uani 1 1 d . . . . .
C9 C 0.2656(4) 0.7246(6) 0.1075(4) 0.0609(13) Uani 1 1 d . . . . .
C10 C 0.2525(5) 0.5658(6) 0.0585(4) 0.0766(18) Uani 1 1 d . . . . .
H10A H 0.145630 0.510991 0.009872 0.092 Uiso 1 1 calc R U . . .
H10B H 0.331878 0.560117 -0.005993 0.092 Uiso 1 1 calc R U . . .
C11 C 0.2788(4) 0.4958(5) 0.1710(5) 0.0620(14) Uani 1 1 d . . . . .
C12 C 0.3496(5) 0.3837(7) 0.1523(8) 0.101(3) Uani 1 1 d . . . . .
H12 H 0.380391 0.351903 0.066543 0.122 Uiso 1 1 calc R U . . .
C13 C 0.3725(6) 0.3240(6) 0.2541(12) 0.123(4) Uani 1 1 d . . . . .
H13 H 0.420669 0.250976 0.240823 0.147 Uiso 1 1 calc R U . . .
C14 C 0.3257(5) 0.3686(4) 0.3802(7) 0.081(2) Uani 1 1 d . . . . .
C15 C 0.2523(4) 0.4763(4) 0.3931(5) 0.0497(10) Uani 1 1 d . . . . .
C16 C 0.2024(5) 0.5228(4) 0.5177(4) 0.0538(10) Uani 1 1 d . . . . .
H16 H 0.152226 0.594473 0.527448 0.065 Uiso 1 1 calc R U . . .
C17 C 0.2254(7) 0.4657(5) 0.6257(6) 0.0839(19) Uani 1 1 d . . . . .
H17 H 0.189424 0.496451 0.709358 0.101 Uiso 1 1 calc R U . . .
C18 C 0.3005(10) 0.3641(7) 0.6131(11) 0.134(5) Uani 1 1 d . . . . .
H18 H 0.319381 0.328919 0.689999 0.160 Uiso 1 1 calc R U . . .
C19 C 0.3468(7) 0.3143(6) 0.4991(12) 0.124(4) Uani 1 1 d . . . . .
H19 H 0.394935 0.241537 0.493973 0.149 Uiso 1 1 calc R U . . .
F1 F 0.2387(4) 0.9257(6) 0.0308(4) 0.1123(17) Uani 1 1 d . . . . .
F2 F 0.0815(3) 0.7144(6) -0.0709(4) 0.135(2) Uani 1 1 d . . . . .
F3 F 0.3291(4) 0.7811(5) -0.1043(3) 0.1191(17) Uani 1 1 d . . . . .
N1 N 0.2304(3) 0.5378(3) 0.2878(3) 0.0423(7) Uani 1 1 d . . . . .
N2 N 0.5605(3) 0.7987(4) 0.1256(3) 0.0548(9) Uani 1 1 d . . . . .
O1 O 0.1530(3) 0.7426(4) 0.1977(3) 0.0559(8) Uani 1 1 d . . . . .
H1 H 0.155208 0.696751 0.258245 0.084 Uiso 1 1 calc R U . . .
S1 S 0.46044(11) 0.94886(10) 0.31732(9) 0.0429(3) Uani 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
C1 N2 1.289(4) . ?
C1 C9 1.519(5) . ?
C1 S1 1.743(4) . ?
C2 C3 1.391(5) . ?
C2 N2 1.392(4) . ?
C2 C7 1.396(5) . ?
C3 C4 1.397(5) . ?
C3 S1 1.726(4) . ?
C4 C5 1.369(7) . ?
C4 H4 0.9500 . ?
C5 C6 1.380(7) . ?
C5 H5 0.9500 . ?
C6 C7 1.375(6) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 F2 1.327(6) . ?
C8 F1 1.334(10) . ?
C8 F3 1.353(7) . ?
C8 C9 1.528(8) . ?
C9 O1 1.416(4) . ?
C9 C10 1.530(8) . ?
C10 C11 1.501(8) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 N1 1.316(5) . ?
C11 C12 1.438(8) . ?
C12 C13 1.333(12) . ?
C12 H12 0.9500 . ?
C13 C14 1.398(11) . ?
C13 H13 0.9500 . ?
C14 C15 1.416(5) . ?
C14 C19 1.450(11) . ?
C15 N1 1.374(5) . ?
C15 C16 1.401(6) . ?
C16 C17 1.372(6) . ?
C16 H16 0.9500 . ?
C17 C18 1.373(10) . ?
C17 H17 0.9500 . ?
C18 C19 1.305(14) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
O1 H1 0.8400 . ?

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
N2 C1 C9 124.2(3) . . ?
N2 C1 S1 116.3(3) . . ?
C9 C1 S1 119.5(3) . . ?
C3 C2 N2 114.7(3) . . ?
C3 C2 C7 119.9(3) . . ?
N2 C2 C7 125.3(3) . . ?
C2 C3 C4 120.7(4) . . ?
C2 C3 S1 109.9(3) . . ?
C4 C3 S1 129.4(3) . . ?
C5 C4 C3 118.2(4) . . ?
C5 C4 H4 120.9 . . ?
C3 C4 H4 120.9 . . ?
C4 C5 C6 121.5(4) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C7 C6 C5 120.9(4) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C6 C7 C2 118.8(4) . . ?
C6 C7 H7 120.6 . . ?
C2 C7 H7 120.6 . . ?
F2 C8 F1 107.9(8) . . ?
F2 C8 F3 107.0(5) . . ?
F1 C8 F3 107.1(6) . . ?
F2 C8 C9 112.1(6) . . ?
F1 C8 C9 111.5(5) . . ?
F3 C8 C9 111.0(7) . . ?
O1 C9 C1 110.5(3) . . ?
O1 C9 C8 103.9(4) . . ?
C1 C9 C8 108.2(4) . . ?
O1 C9 C10 112.8(4) . . ?
C1 C9 C10 110.5(4) . . ?
C8 C9 C10 110.7(5) . . ?
C11 C10 C9 113.1(3) . . ?
C11 C10 H10A 109.0 . . ?
C9 C10 H10A 109.0 . . ?
C11 C10 H10B 109.0 . . ?
C9 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
N1 C11 C12 120.5(6) . . ?
N1 C11 C10 117.6(4) . . ?
C12 C11 C10 121.9(5) . . ?
C13 C12 C11 120.7(6) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C14 120.1(5) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C13 C14 C15 117.3(6) . . ?
C13 C14 C19 125.4(6) . . ?
C15 C14 C19 117.3(6) . . ?
N1 C15 C16 119.0(3) . . ?
N1 C15 C14 122.0(5) . . ?
C16 C15 C14 119.0(5) . . ?
C17 C16 C15 120.4(5) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C16 C17 C18 120.1(7) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C19 C18 C17 122.3(7) . . ?
C19 C18 H18 118.8 . . ?
C17 C18 H18 118.8 . . ?
C18 C19 C14 120.8(5) . . ?
C18 C19 H19 119.6 . . ?
C14 C19 H19 119.6 . . ?
C11 N1 C15 119.3(4) . . ?
C1 N2 C2 110.4(3) . . ?
C9 O1 H1 109.5 . . ?
C3 S1 C1 88.68(16) . . ?

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
N2 C2 C3 C4 177.3(4) . . . . ?
C7 C2 C3 C4 -0.7(6) . . . . ?
N2 C2 C3 S1 -1.1(4) . . . . ?
C7 C2 C3 S1 -179.1(3) . . . . ?
C2 C3 C4 C5 0.4(6) . . . . ?
S1 C3 C4 C5 178.5(3) . . . . ?
C3 C4 C5 C6 0.3(6) . . . . ?
C4 C5 C6 C7 -0.9(7) . . . . ?
C5 C6 C7 C2 0.6(7) . . . . ?
C3 C2 C7 C6 0.2(7) . . . . ?
N2 C2 C7 C6 -177.6(4) . . . . ?
N2 C1 C9 O1 165.3(4) . . . . ?
S1 C1 C9 O1 -13.8(5) . . . . ?
N2 C1 C9 C8 -81.6(7) . . . . ?
S1 C1 C9 C8 99.3(5) . . . . ?
N2 C1 C9 C10 39.7(6) . . . . ?
S1 C1 C9 C10 -139.4(3) . . . . ?
F2 C8 C9 O1 -62.1(8) . . . . ?
F1 C8 C9 O1 59.0(5) . . . . ?
F3 C8 C9 O1 178.3(5) . . . . ?
F2 C8 C9 C1 -179.6(6) . . . . ?
F1 C8 C9 C1 -58.5(6) . . . . ?
F3 C8 C9 C1 60.8(8) . . . . ?
F2 C8 C9 C10 59.3(8) . . . . ?
F1 C8 C9 C10 -179.7(4) . . . . ?
F3 C8 C9 C10 -60.4(6) . . . . ?
O1 C9 C10 C11 -60.3(4) . . . . ?
C1 C9 C10 C11 63.9(4) . . . . ?
C8 C9 C10 C11 -176.3(3) . . . . ?
C9 C10 C11 N1 33.7(4) . . . . ?
C9 C10 C11 C12 -148.2(4) . . . . ?
N1 C11 C12 C13 -2.3(6) . . . . ?
C10 C11 C12 C13 179.6(4) . . . . ?
C11 C12 C13 C14 0.9(8) . . . . ?
C12 C13 C14 C15 1.0(7) . . . . ?
C12 C13 C14 C19 -178.7(5) . . . . ?
C13 C14 C15 N1 -1.5(5) . . . . ?
C19 C14 C15 N1 178.2(4) . . . . ?
C13 C14 C15 C16 179.4(4) . . . . ?
C19 C14 C15 C16 -0.9(5) . . . . ?
N1 C15 C16 C17 -178.6(4) . . . . ?
C14 C15 C16 C17 0.5(6) . . . . ?
C15 C16 C17 C18 1.2(7) . . . . ?
C16 C17 C18 C19 -2.6(9) . . . . ?
C17 C18 C19 C14 2.2(10) . . . . ?
C13 C14 C19 C18 179.2(6) . . . . ?
C15 C14 C19 C18 -0.4(8) . . . . ?
C12 C11 N1 C15 1.8(5) . . . . ?
C10 C11 N1 C15 180.0(3) . . . . ?
C16 C15 N1 C11 179.2(3) . . . . ?
C14 C15 N1 C11 0.1(5) . . . . ?
C9 C1 N2 C2 179.7(4) . . . . ?
S1 C1 N2 C2 -1.2(5) . . . . ?
C3 C2 N2 C1 1.5(5) . . . . ?
C7 C2 N2 C1 179.4(4) . . . . ?
C2 C3 S1 C1 0.3(3) . . . . ?
C4 C3 S1 C1 -177.9(4) . . . . ?
N2 C1 S1 C3 0.5(4) . . . . ?
C9 C1 S1 C3 179.7(4) . . . . ?

_refine_diff_density_max         0.776
_refine_diff_density_min         -0.823
_refine_diff_density_rms         0.095



