# 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_ZJL2
_database_code_depnum_ccdc_archive 'CCDC 2071603'
loop_
_audit_author_name
_audit_author_address
'Jinli Zhang' 'Nanjing Tech University'
_audit_update_record             
;
2021-03-19 deposited with the CCDC.	2023-03-24 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H18 F3 N S'
_chemical_formula_iupac          ?
_chemical_formula_weight         349.40
_chemical_absolute_configuration ?

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   16.8319(12)
_cell_length_b                   15.3118(13)
_cell_length_c                   6.5989(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1700.7(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9988
_cell_measurement_theta_min      3.5978
_cell_measurement_theta_max      30.2382
_cell_measurement_temperature    293.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728

_exptl_absorpt_coefficient_mu    0.220
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.56
_exptl_absorpt_correction_T_max  0.96

_exptl_special_details           
;
;

_diffrn_ambient_temperature      293.(2)

_diffrn_source                   ?
_diffrn_source_type              ?
_diffrn_source_power             ?
_diffrn_source_current           ?
_diffrn_source_voltage           ?

_diffrn_radiation_probe          ?
_diffrn_radiation_type           ?
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device       ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            22068
_diffrn_reflns_av_R_equivalents  0.0732
_diffrn_reflns_av_unetI/netI     0.0479
_diffrn_reflns_theta_min         3.57
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       8

_refine_special_details          
;
;

_reflns_number_total             3748
_reflns_number_gt                3038
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.717
_reflns_Friedel_fraction_max     0.836
_reflns_Friedel_fraction_full    0.878

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0982
_refine_ls_R_factor_gt           0.0741
_refine_ls_wR_factor_gt          0.1558
_refine_ls_wR_factor_ref         0.1722
_refine_ls_goodness_of_fit_ref   1.174
_refine_ls_restrained_S_all      1.174
_refine_ls_number_reflns         3748
_refine_ls_number_parameters     195
_refine_ls_number_restraints     1
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0403P)²+2.6850P] 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         0.425
_refine_diff_density_min         -0.346
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 1037 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(5)

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       ?
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_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 0.53516(17) 0.1174(3) 0.1729(6) 0.0454(14) Uani d . . G 1 . .
H H1 0.590285 0.120523 0.179501 0.054 Uiso calc U . R 1 . .
C C2 0.4989(3) 0.0663(3) 0.0256(6) 0.0562(18) Uani d . . G 1 . .
H H2 0.529686 0.035126 -0.06636 0.067 Uiso calc U . R 1 . .
C C3 0.4165(3) 0.0616(3) 0.0158(7) 0.064(2) Uani d . . G 1 . .
H H3 0.392183 0.027388 -0.082758 0.077 Uiso calc U . R 1 . .
C C4 0.37040(18) 0.1081(4) 0.1533(9) 0.071(2) Uani d . . G 1 . .
H H4 0.315278 0.105046 0.146704 0.085 Uiso calc U . R 1 . .
C C5 0.4067(2) 0.1593(3) 0.3006(8) 0.0595(19) Uani d . . G 1 . .
H H5 0.375875 0.190444 0.392566 0.071 Uiso calc U . R 1 . .
C C6 0.4891(2) 0.1640(3) 0.3104(6) 0.0389(13) Uani d . . G 1 . .
C C7 0.5264(3) 0.2158(4) 0.4709(9) 0.0365(13) Uani d . . . 1 . .
C C8 0.5019(3) 0.2290(4) 0.6576(10) 0.0391(13) Uani d . . . 1 . .
H H8 0.457302 0.200492 0.708209 0.047 Uiso calc U . R 1 . .
C C9 0.5486(3) 0.2918(4) 0.7869(9) 0.0338(12) Uani d . . . 1 . .
H H9 0.558639 0.26371 0.917795 0.041 Uiso calc U . R 1 . .
C C10 0.6310(3) 0.3035(4) 0.6753(9) 0.0323(11) Uani d . . . 1 . .
C C11 0.6889(4) 0.2359(4) 0.7589(11) 0.0456(15) Uani d . . . 1 . .
C C12 0.6690(2) 0.3927(2) 0.6999(6) 0.0333(12) Uani d . . G 1 . .
C C13 0.6678(2) 0.4340(3) 0.8874(5) 0.0442(15) Uani d . . G 1 . .
H H13 0.642521 0.407548 0.996783 0.053 Uiso calc U . R 1 . .
C C14 0.7042(2) 0.5147(3) 0.9115(7) 0.0547(17) Uani d . . G 1 . .
H H14 0.703396 0.542375 1.037028 0.066 Uiso calc U . R 1 . .
C C15 0.7420(3) 0.5542(2) 0.7481(9) 0.065(2) Uani d . . G 1 . .
H H15 0.766369 0.608278 0.76423 0.078 Uiso calc U . R 1 . .
C C16 0.7432(3) 0.5129(3) 0.5605(7) 0.063(2) Uani d . . G 1 . .
H H16 0.768467 0.539354 0.451185 0.075 Uiso calc U . R 1 . .
C C17 0.7068(3) 0.4322(3) 0.5364(5) 0.0483(16) Uani d . . G 1 . .
H H17 0.707593 0.404526 0.410935 0.058 Uiso calc U . R 1 . .
C C18 0.4476(4) 0.3633(5) 0.9810(14) 0.065(2) Uani d . . . 1 . .
H H18A 0.410884 0.318249 0.942828 0.098 Uiso calc U . R 1 . .
H H18B 0.419625 0.417412 0.997583 0.098 Uiso calc U . R 1 . .
H H18C 0.47289 0.347727 1.106367 0.098 Uiso calc U . R 1 . .
C C19 0.4754(5) 0.4154(5) 0.6456(14) 0.064(2) Uani d . . . 1 . .
H H19A 0.516288 0.420117 0.544777 0.096 Uiso calc U . R 1 . .
H H19B 0.456759 0.472685 0.680805 0.096 Uiso calc U . R 1 . .
H H19C 0.432115 0.381508 0.5929 0.096 Uiso calc U . R 1 . .
F F1 0.6626(3) 0.1547(2) 0.7446(7) 0.0626(12) Uani d . . . 1 . .
F F2 0.7041(2) 0.2491(3) 0.9570(6) 0.0608(11) Uani d . . . 1 . .
F F3 0.7586(2) 0.2384(3) 0.6667(7) 0.0608(12) Uani d . . . 1 . .
N N1 0.5072(3) 0.3730(3) 0.8246(8) 0.0401(12) Uani d . . . 1 . .
S S1 0.61477(8) 0.27320(10) 0.4108(3) 0.0418(4) 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 C2 . 1.39 ?
C1 C6 . 1.39 ?
C2 C3 . 1.39 ?
C3 C4 . 1.39 ?
C4 C5 . 1.39 ?
C5 C6 . 1.39 ?
C6 C7 . 1.465(7) ?
C7 C8 . 1.315(9) ?
C7 S1 . 1.773(6) ?
C8 C9 . 1.507(8) ?
C9 N1 . 1.446(7) ?
C9 C10 . 1.581(7) ?
C10 C12 . 1.516(6) ?
C10 C11 . 1.526(8) ?
C10 S1 . 1.827(6) ?
C11 F3 . 1.322(7) ?
C11 F1 . 1.322(7) ?
C11 F2 . 1.347(8) ?
C12 C13 . 1.39 ?
C12 C17 . 1.39 ?
C13 C14 . 1.39 ?
C14 C15 . 1.39 ?
C15 C16 . 1.39 ?
C16 C17 . 1.39 ?
C18 N1 . 1.447(8) ?
C19 N1 . 1.450(9) ?

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
C2 C1 C6 . . 120.0 ?
C1 C2 C3 . . 120.0 ?
C4 C3 C2 . . 120.0 ?
C3 C4 C5 . . 120.0 ?
C4 C5 C6 . . 120.0 ?
C5 C6 C1 . . 120.0 ?
C5 C6 C7 . . 119.3(3) ?
C1 C6 C7 . . 120.7(3) ?
C8 C7 C6 . . 128.8(5) ?
C8 C7 S1 . . 113.4(5) ?
C6 C7 S1 . . 117.8(4) ?
C7 C8 C9 . . 117.7(5) ?
N1 C9 C8 . . 113.3(5) ?
N1 C9 C10 . . 113.9(4) ?
C8 C9 C10 . . 105.5(5) ?
C12 C10 C11 . . 107.6(4) ?
C12 C10 C9 . . 115.0(4) ?
C11 C10 C9 . . 108.4(5) ?
C12 C10 S1 . . 113.2(4) ?
C11 C10 S1 . . 105.6(4) ?
C9 C10 S1 . . 106.5(4) ?
F3 C11 F1 . . 107.0(6) ?
F3 C11 F2 . . 105.9(5) ?
F1 C11 F2 . . 105.9(6) ?
F3 C11 C10 . . 112.4(5) ?
F1 C11 C10 . . 113.4(5) ?
F2 C11 C10 . . 111.7(5) ?
C13 C12 C17 . . 120.0 ?
C13 C12 C10 . . 119.9(3) ?
C17 C12 C10 . . 120.1(3) ?
C14 C13 C12 . . 120.0 ?
C13 C14 C15 . . 120.0 ?
C16 C15 C14 . . 120.0 ?
C15 C16 C17 . . 120.0 ?
C16 C17 C12 . . 120.0 ?
C9 N1 C18 . . 111.6(5) ?
C9 N1 C19 . . 115.0(5) ?
C18 N1 C19 . . 111.8(6) ?
C7 S1 C10 . . 92.2(3) ?



