# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_sjg-5-58
_database_code_depnum_ccdc_archive 'CCDC 2079361'
loop_
_audit_author_name
_audit_author_address
'Hao Xie'
;Peking University Shenzhen Graduate School
China
;
_audit_update_record             
;
2021-04-22 deposited with the CCDC.	2021-07-05 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 H16 F N O3 S'
_chemical_formula_weight         357.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.4897(2)
_cell_length_b                   7.49150(10)
_cell_length_c                   20.1739(4)
_cell_angle_alpha                90
_cell_angle_beta                 104.029(2)
_cell_angle_gamma                90
_cell_volume                     1684.68(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    179.99(10)
_cell_measurement_reflns_used    12351
_cell_measurement_theta_min      4.0410
_cell_measurement_theta_max      76.0680

_exptl_crystal_description       block
_exptl_crystal_colour            clear
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_F_000             744
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    1.964
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.54175
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17636
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         4.060
_diffrn_reflns_theta_max         76.690
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3426
_reflns_number_gt                3258
_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 2018/2 (Sheldrick, 2018)'
_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)+(0.0585P)²+1.7464P] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0011(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3426
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0556
_refine_ls_wR_factor_ref         0.1454
_refine_ls_wR_factor_gt          0.1443
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.091
_refine_ls_shift/su_max          0.001
_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
S23 S 0.31379(5) -0.02022(9) 0.80669(3) 0.0410(2) Uani 1 1 d . . . . .
F10 F 0.42715(16) 0.2564(3) 0.40779(8) 0.0635(5) Uani 1 1 d . . . . .
O18 O 0.54484(13) 0.3696(2) 0.84245(8) 0.0392(4) Uani 1 1 d . . . . .
O8 O 0.29296(15) -0.0418(2) 0.67135(9) 0.0418(4) Uani 1 1 d . . . . .
N N 0.46511(17) 0.2329(3) 0.84628(10) 0.0393(5) Uani 1 1 d . . . . .
O24 O 0.4819(2) 0.2671(4) 0.96050(10) 0.0733(8) Uani 1 1 d . . . . .
C1 C 0.3864(2) 0.1226(3) 0.59799(12) 0.0352(5) Uani 1 1 d . . . . .
C9 C 0.43076(19) 0.1740(3) 0.72568(12) 0.0354(5) Uani 1 1 d . . . . .
H9 H 0.487421 0.262548 0.720972 0.042 Uiso 1 1 calc R U . . .
C7 C 0.36668(19) 0.0754(3) 0.66659(12) 0.0347(5) Uani 1 1 d . . . . .
C19 C 0.41026(19) 0.1407(3) 0.78762(12) 0.0350(5) Uani 1 1 d . . . . .
C11 C 0.5676(2) 0.6832(3) 0.83019(13) 0.0391(5) Uani 1 1 d . . . . .
C16 C 0.6260(2) 0.7804(4) 0.88724(13) 0.0428(6) Uani 1 1 d . . . . .
H16 H 0.614009 0.751069 0.930907 0.051 Uiso 1 1 calc R U . . .
C6 C 0.4925(2) 0.2010(4) 0.59029(13) 0.0408(5) Uani 1 1 d . . . . .
H6 H 0.555618 0.224555 0.629423 0.049 Uiso 1 1 calc R U . . .
C2 C 0.2944(2) 0.0904(4) 0.54009(13) 0.0433(6) Uani 1 1 d . . . . .
H2 H 0.222095 0.036288 0.544868 0.052 Uiso 1 1 calc R U . . .
C15 C 0.7017(2) 0.9198(4) 0.88079(14) 0.0482(6) Uani 1 1 d . . . . .
H15 H 0.739825 0.987454 0.919842 0.058 Uiso 1 1 calc R U . . .
C21 C 0.4385(2) 0.1917(4) 0.90728(13) 0.0512(7) Uani 1 1 d . . . . .
C5 C 0.5064(2) 0.2447(4) 0.52620(14) 0.0459(6) Uani 1 1 d . . . . .
H5 H 0.578981 0.296129 0.520645 0.055 Uiso 1 1 calc R U . . .
C3 C 0.3068(2) 0.1362(4) 0.47580(13) 0.0480(6) Uani 1 1 d . . . . .
H3 H 0.243761 0.115661 0.436346 0.058 Uiso 1 1 calc R U . . .
C4 C 0.4130(2) 0.2121(4) 0.47064(13) 0.0465(6) Uani 1 1 d . . . . .
C14 C 0.7219(3) 0.9605(4) 0.81800(16) 0.0515(7) Uani 1 1 d . . . . .
H14 H 0.774768 1.055143 0.813881 0.062 Uiso 1 1 calc R U . . .
C22 C 0.3484(2) 0.0388(4) 0.89760(14) 0.0525(7) Uani 1 1 d . . . . .
H22 H 0.387996 -0.066005 0.924578 0.063 Uiso 1 1 calc R U . . .
C12 C 0.5877(3) 0.7268(4) 0.76733(14) 0.0494(6) Uani 1 1 d . . . . .
H12 H 0.547821 0.662029 0.727845 0.059 Uiso 1 1 calc R U . . .
C13 C 0.6656(3) 0.8644(4) 0.76127(16) 0.0572(7) Uani 1 1 d . . . . .
H13 H 0.679946 0.891887 0.717969 0.069 Uiso 1 1 calc R U . . .
C17 C 0.4809(2) 0.5406(4) 0.83689(16) 0.0493(7) Uani 1 1 d . . . . .
H17A H 0.450270 0.561337 0.878082 0.059 Uiso 1 1 calc R U . . .
H17B H 0.412020 0.540253 0.796400 0.059 Uiso 1 1 calc R U . . .
C25 C 0.2390(3) 0.0852(4) 0.92159(16) 0.0572(7) Uani 1 1 d . . . . .
H25A H 0.196692 0.183881 0.894076 0.086 Uiso 1 1 calc R U . . .
H25B H 0.262577 0.121192 0.969697 0.086 Uiso 1 1 calc R U . . .
H25C H 0.186073 -0.018989 0.916755 0.086 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
S23 C19 1.743(2) . ?
S23 C22 1.834(3) . ?
F10 C4 1.358(3) . ?
O18 N 1.389(3) . ?
O18 C17 1.468(3) . ?
O8 C7 1.240(3) . ?
N C21 1.373(3) . ?
N C19 1.383(3) . ?
O24 C21 1.209(3) . ?
C1 C2 1.393(3) . ?
C1 C6 1.396(3) . ?
C1 C7 1.498(3) . ?
C9 C19 1.350(3) . ?
C9 C7 1.444(3) . ?
C9 H9 0.9500 . ?
C11 C12 1.382(4) . ?
C11 C16 1.390(3) . ?
C11 C17 1.489(4) . ?
C16 C15 1.385(4) . ?
C16 H16 0.9500 . ?
C6 C5 1.380(4) . ?
C6 H6 0.9500 . ?
C2 C3 1.382(4) . ?
C2 H2 0.9500 . ?
C15 C14 1.376(4) . ?
C15 H15 0.9500 . ?
C21 C22 1.525(4) . ?
C5 C4 1.372(4) . ?
C5 H5 0.9500 . ?
C3 C4 1.373(4) . ?
C3 H3 0.9500 . ?
C14 C13 1.374(4) . ?
C14 H14 0.9500 . ?
C22 C25 1.492(4) . ?
C22 H22 1.0000 . ?
C12 C13 1.390(4) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?

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
C19 S23 C22 93.37(12) . . ?
N O18 C17 108.86(17) . . ?
C21 N C19 120.0(2) . . ?
C21 N O18 120.58(19) . . ?
C19 N O18 119.39(19) . . ?
C2 C1 C6 119.0(2) . . ?
C2 C1 C7 118.7(2) . . ?
C6 C1 C7 122.3(2) . . ?
C19 C9 C7 120.1(2) . . ?
C19 C9 H9 120.0 . . ?
C7 C9 H9 120.0 . . ?
O8 C7 C9 121.3(2) . . ?
O8 C7 C1 119.9(2) . . ?
C9 C7 C1 118.8(2) . . ?
C9 C19 N 123.6(2) . . ?
C9 C19 S23 126.55(18) . . ?
N C19 S23 109.81(17) . . ?
C12 C11 C16 118.8(2) . . ?
C12 C11 C17 121.1(2) . . ?
C16 C11 C17 120.0(2) . . ?
C15 C16 C11 120.4(2) . . ?
C15 C16 H16 119.8 . . ?
C11 C16 H16 119.8 . . ?
C5 C6 C1 120.4(2) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
C3 C2 C1 120.9(2) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C14 C15 C16 120.2(3) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
O24 C21 N 123.9(3) . . ?
O24 C21 C22 125.8(3) . . ?
N C21 C22 110.2(2) . . ?
C4 C5 C6 118.6(2) . . ?
C4 C5 H5 120.7 . . ?
C6 C5 H5 120.7 . . ?
C4 C3 C2 118.0(2) . . ?
C4 C3 H3 121.0 . . ?
C2 C3 H3 121.0 . . ?
F10 C4 C5 118.2(3) . . ?
F10 C4 C3 118.8(2) . . ?
C5 C4 C3 123.0(2) . . ?
C13 C14 C15 120.0(3) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C25 C22 C21 112.5(3) . . ?
C25 C22 S23 112.7(2) . . ?
C21 C22 S23 106.55(19) . . ?
C25 C22 H22 108.3 . . ?
C21 C22 H22 108.3 . . ?
S23 C22 H22 108.3 . . ?
C11 C12 C13 120.7(3) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C14 C13 C12 119.9(3) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
O18 C17 C11 107.43(19) . . ?
O18 C17 H17A 110.2 . . ?
C11 C17 H17A 110.2 . . ?
O18 C17 H17B 110.2 . . ?
C11 C17 H17B 110.2 . . ?
H17A C17 H17B 108.5 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?

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
C17 O18 N C21 -81.8(3) . . . . ?
C17 O18 N C19 96.7(2) . . . . ?
C19 C9 C7 O8 -0.6(3) . . . . ?
C19 C9 C7 C1 176.6(2) . . . . ?
C2 C1 C7 O8 24.9(3) . . . . ?
C6 C1 C7 O8 -156.5(2) . . . . ?
C2 C1 C7 C9 -152.4(2) . . . . ?
C6 C1 C7 C9 26.2(3) . . . . ?
C7 C9 C19 N -177.9(2) . . . . ?
C7 C9 C19 S23 2.1(3) . . . . ?
C21 N C19 C9 179.4(2) . . . . ?
O18 N C19 C9 0.9(3) . . . . ?
C21 N C19 S23 -0.6(3) . . . . ?
O18 N C19 S23 -179.16(15) . . . . ?
C22 S23 C19 C9 180.0(2) . . . . ?
C22 S23 C19 N 0.05(19) . . . . ?
C12 C11 C16 C15 0.8(4) . . . . ?
C17 C11 C16 C15 -176.4(2) . . . . ?
C2 C1 C6 C5 -0.5(4) . . . . ?
C7 C1 C6 C5 -179.1(2) . . . . ?
C6 C1 C2 C3 -0.4(4) . . . . ?
C7 C1 C2 C3 178.2(2) . . . . ?
C11 C16 C15 C14 -1.5(4) . . . . ?
C19 N C21 O24 -179.4(3) . . . . ?
O18 N C21 O24 -0.8(5) . . . . ?
C19 N C21 C22 0.9(4) . . . . ?
O18 N C21 C22 179.5(2) . . . . ?
C1 C6 C5 C4 1.1(4) . . . . ?
C1 C2 C3 C4 0.8(4) . . . . ?
C6 C5 C4 F10 179.6(2) . . . . ?
C6 C5 C4 C3 -0.8(4) . . . . ?
C2 C3 C4 F10 179.4(2) . . . . ?
C2 C3 C4 C5 -0.2(4) . . . . ?
C16 C15 C14 C13 0.9(4) . . . . ?
O24 C21 C22 C25 55.6(4) . . . . ?
N C21 C22 C25 -124.7(3) . . . . ?
O24 C21 C22 S23 179.5(3) . . . . ?
N C21 C22 S23 -0.8(3) . . . . ?
C19 S23 C22 C25 124.2(2) . . . . ?
C19 S23 C22 C21 0.4(2) . . . . ?
C16 C11 C12 C13 0.5(4) . . . . ?
C17 C11 C12 C13 177.7(3) . . . . ?
C15 C14 C13 C12 0.4(5) . . . . ?
C11 C12 C13 C14 -1.1(4) . . . . ?
N O18 C17 C11 -177.8(2) . . . . ?
C12 C11 C17 O18 85.1(3) . . . . ?
C16 C11 C17 O18 -97.8(3) . . . . ?

_refine_diff_density_max         0.907
_refine_diff_density_min         -0.487
_refine_diff_density_rms         0.055

