# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_xlt-1
_database_code_depnum_ccdc_archive 'CCDC 2127108'
loop_
_audit_author_name
_audit_author_address
'Xueliang Huang'
;College of Chemistry and Chemical Engineering, Hunan Normal University
China
;
_audit_update_record             
;
2021-12-08 deposited with the CCDC.	2022-01-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H19 N O3 S'
_chemical_formula_weight         401.46

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0147 0.0070 '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'
N N 0.0253 0.0135 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0412 0.0250 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.2922 0.4242 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pca2(1)

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   8.25955(8)
_cell_length_b                   10.43795(9)
_cell_length_c                   22.5124(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1940.86(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.01(10)
_cell_measurement_reflns_used    48340
_cell_measurement_theta_min      3.4290
_cell_measurement_theta_max      60.5680

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             840
_exptl_absorpt_coefficient_mu    1.096
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.48295
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.82a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100.01(10)
_diffrn_radiation_wavelength     1.34150
_diffrn_radiation_type           'Ga K\a'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            52483
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_sigmaI/netI    0.0111
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.41
_diffrn_reflns_theta_max         60.60
_reflns_number_total             4408
_reflns_number_gt                4392
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0376P)²+0.3889P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0022(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.020(12)
_refine_ls_number_reflns         4408
_refine_ls_number_parameters     264
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0222
_refine_ls_R_factor_gt           0.0221
_refine_ls_wR_factor_ref         0.0611
_refine_ls_wR_factor_gt          0.0611
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.038
_refine_ls_shift/su_mean         0.001

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C5 C 0.68901(14) 0.74077(12) 0.29768(5) 0.0194(2) Uani 1 1 d . . .
H5 H 0.5932 0.6967 0.2904 0.023 Uiso 1 1 calc R . .
C6 C 0.79279(13) 0.69949(11) 0.34267(5) 0.0167(2) Uani 1 1 d . . .
C15 C 0.78990(18) 0.06777(12) 0.43470(6) 0.0295(3) Uani 1 1 d . . .
H15 H 0.7898 -0.0190 0.4252 0.035 Uiso 1 1 calc R . .
C16 C 0.70833(17) 0.11095(13) 0.48485(6) 0.0288(3) Uani 1 1 d . . .
H16 H 0.6531 0.0532 0.5089 0.035 Uiso 1 1 calc R . .
C17 C 0.70942(16) 0.24030(12) 0.49895(6) 0.0221(2) Uani 1 1 d . . .
H17 H 0.6559 0.2686 0.5328 0.027 Uiso 1 1 calc R . .
C18 C 0.63437(14) 0.72112(11) 0.63029(5) 0.0185(2) Uani 1 1 d . . .
C19 C 0.50894(15) 0.80618(12) 0.61828(5) 0.0230(2) Uani 1 1 d . . .
H19 H 0.5190 0.8671 0.5884 0.028 Uiso 1 1 calc R . .
C20 C 0.36858(15) 0.79812(12) 0.65186(5) 0.0239(2) Uani 1 1 d . . .
H20 H 0.2833 0.8538 0.6441 0.029 Uiso 1 1 calc R . .
C21 C 0.35355(14) 0.70679(11) 0.69745(5) 0.0196(2) Uani 1 1 d . . .
C22 C 0.47939(14) 0.62088(11) 0.70691(5) 0.0199(2) Uani 1 1 d . . .
H22 H 0.4687 0.5583 0.7361 0.024 Uiso 1 1 calc R . .
C23 C 0.62053(15) 0.62669(11) 0.67375(5) 0.0201(2) Uani 1 1 d . . .
H23 H 0.7042 0.5688 0.6804 0.024 Uiso 1 1 calc R . .
C24 C 0.20645(15) 0.70435(13) 0.73656(6) 0.0246(2) Uani 1 1 d . . .
H24A H 0.1118 0.6906 0.7127 0.037 Uiso 1 1 calc R . .
H24B H 0.1970 0.7846 0.7571 0.037 Uiso 1 1 calc R . .
H24C H 0.2165 0.6362 0.7650 0.037 Uiso 1 1 calc R . .
C14 C 0.87134(16) 0.15425(12) 0.39889(6) 0.0246(2) Uani 1 1 d . . .
H14 H 0.9268 0.1253 0.3655 0.030 Uiso 1 1 calc R . .
C13 C 0.87052(14) 0.28393(11) 0.41252(5) 0.0200(2) Uani 1 1 d . . .
H13 H 0.9241 0.3415 0.3879 0.024 Uiso 1 1 calc R . .
C12 C 0.78999(13) 0.32854(11) 0.46289(5) 0.0168(2) Uani 1 1 d . . .
C4 C 0.72813(15) 0.84729(11) 0.26376(5) 0.0221(2) Uani 1 1 d . . .
H4 H 0.6577 0.8755 0.2343 0.026 Uiso 1 1 calc R . .
C11 C 0.79159(12) 0.46546(11) 0.47896(5) 0.0174(2) Uani 1 1 d . . .
O3 O 0.94349(10) 0.68387(9) 0.63007(4) 0.02630(19) Uani 1 1 d . . .
C3 C 0.87234(16) 0.91151(11) 0.27386(5) 0.0226(2) Uani 1 1 d . . .
H3 H 0.8989 0.9826 0.2510 0.027 Uiso 1 1 calc R . .
O2 O 0.83505(12) 0.86533(9) 0.57083(4) 0.0263(2) Uani 1 1 d . . .
C2 C 0.97740(15) 0.87014(11) 0.31805(5) 0.0210(2) Uani 1 1 d . . .
H2 H 1.0745 0.9131 0.3243 0.025 Uiso 1 1 calc R . .
O1 O 0.66913(11) 0.49636(9) 0.35217(4) 0.02440(19) Uani 1 1 d . . .
S1 S 0.82020(3) 0.73831(3) 0.593769(13) 0.01945(8) Uani 1 1 d . . .
C1 C 0.93788(14) 0.76425(10) 0.35311(5) 0.0179(2) Uani 1 1 d . . .
H1 H 1.0075 0.7372 0.3831 0.021 Uiso 1 1 calc R . .
N1 N 0.80845(12) 0.64257(10) 0.53398(5) 0.0194(2) Uani 1 1 d . . .
C10 C 0.80970(14) 0.50925(12) 0.53571(5) 0.0196(2) Uani 1 1 d . . .
H10 H 0.8209 0.4589 0.5695 0.023 Uiso 1 1 calc R . .
C9 C 0.79158(13) 0.68306(11) 0.47632(5) 0.0184(2) Uani 1 1 d . . .
H9 H 0.7872 0.7678 0.4636 0.022 Uiso 1 1 calc R . .
C8 C 0.78237(13) 0.57668(11) 0.44079(5) 0.0176(2) Uani 1 1 d . . .
C7 C 0.74490(14) 0.58205(10) 0.37680(5) 0.0171(2) 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
C5 C4 1.3870(17) . ?
C5 C6 1.3950(16) . ?
C5 H5 0.9300 . ?
C6 C1 1.3958(16) . ?
C6 C7 1.4998(15) . ?
C15 C14 1.3847(19) . ?
C15 C16 1.3897(19) . ?
C15 H15 0.9300 . ?
C16 C17 1.3870(18) . ?
C16 H16 0.9300 . ?
C17 C12 1.3966(16) . ?
C17 H17 0.9300 . ?
C18 C19 1.3909(17) . ?
C18 C23 1.3934(16) . ?
C18 S1 1.7505(12) . ?
C19 C20 1.3866(17) . ?
C19 H19 0.9300 . ?
C20 C21 1.4063(16) . ?
C20 H20 0.9300 . ?
C21 C22 1.3892(17) . ?
C21 C24 1.5007(16) . ?
C22 C23 1.3857(16) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C14 C13 1.3880(17) . ?
C14 H14 0.9300 . ?
C13 C12 1.3946(16) . ?
C13 H13 0.9300 . ?
C12 C11 1.4742(16) . ?
C4 C3 1.3856(18) . ?
C4 H4 0.9300 . ?
C11 C10 1.3652(16) . ?
C11 C8 1.4462(15) . ?
O3 S1 1.4240(9) . ?
C3 C2 1.3888(18) . ?
C3 H3 0.9300 . ?
O2 S1 1.4281(9) . ?
C2 C1 1.3968(16) . ?
C2 H2 0.9300 . ?
O1 C7 1.2243(14) . ?
S1 N1 1.6792(11) . ?
C1 H1 0.9300 . ?
N1 C9 1.3723(15) . ?
N1 C10 1.3922(15) . ?
C10 H10 0.9300 . ?
C9 C8 1.3706(16) . ?
C9 H9 0.9300 . ?
C8 C7 1.4747(15) . ?

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
C4 C5 C6 120.27(11) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C5 120.01(11) . . ?
C1 C6 C7 122.41(10) . . ?
C5 C6 C7 117.53(10) . . ?
C14 C15 C16 119.80(12) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C17 C16 C15 119.90(12) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C17 C12 120.80(12) . . ?
C16 C17 H17 119.6 . . ?
C12 C17 H17 119.6 . . ?
C19 C18 C23 121.80(11) . . ?
C19 C18 S1 119.76(9) . . ?
C23 C18 S1 118.31(9) . . ?
C18 C19 C20 118.56(11) . . ?
C18 C19 H19 120.7 . . ?
C20 C19 H19 120.7 . . ?
C19 C20 C21 120.86(11) . . ?
C19 C20 H20 119.6 . . ?
C21 C20 H20 119.6 . . ?
C22 C21 C20 118.91(11) . . ?
C22 C21 C24 120.32(11) . . ?
C20 C21 C24 120.75(11) . . ?
C23 C22 C21 121.24(11) . . ?
C23 C22 H22 119.4 . . ?
C21 C22 H22 119.4 . . ?
C22 C23 C18 118.57(11) . . ?
C22 C23 H23 120.7 . . ?
C18 C23 H23 120.7 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C15 C14 C13 120.31(12) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C12 C13 C14 120.51(11) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C13 C12 C17 118.67(11) . . ?
C13 C12 C11 121.26(10) . . ?
C17 C12 C11 120.07(10) . . ?
C3 C4 C5 119.85(11) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C10 C11 C8 107.04(10) . . ?
C10 C11 C12 123.72(10) . . ?
C8 C11 C12 129.19(10) . . ?
C4 C3 C2 120.28(11) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C2 C1 120.32(11) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
O3 S1 O2 121.11(6) . . ?
O3 S1 N1 105.30(5) . . ?
O2 S1 N1 105.52(5) . . ?
O3 S1 C18 108.45(6) . . ?
O2 S1 C18 109.89(6) . . ?
N1 S1 C18 105.35(5) . . ?
C6 C1 C2 119.25(11) . . ?
C6 C1 H1 120.4 . . ?
C2 C1 H1 120.4 . . ?
C9 N1 C10 109.58(10) . . ?
C9 N1 S1 125.51(8) . . ?
C10 N1 S1 124.89(9) . . ?
C11 C10 N1 107.92(10) . . ?
C11 C10 H10 126.0 . . ?
N1 C10 H10 126.0 . . ?
C8 C9 N1 107.94(10) . . ?
C8 C9 H9 126.0 . . ?
N1 C9 H9 126.0 . . ?
C9 C8 C11 107.50(10) . . ?
C9 C8 C7 123.43(10) . . ?
C11 C8 C7 128.46(10) . . ?
O1 C7 C8 121.46(10) . . ?
O1 C7 C6 120.00(10) . . ?
C8 C7 C6 118.43(10) . . ?

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
C4 C5 C6 C1 -0.99(17) . . . . ?
C4 C5 C6 C7 -178.73(10) . . . . ?
C14 C15 C16 C17 -0.3(2) . . . . ?
C15 C16 C17 C12 0.8(2) . . . . ?
C23 C18 C19 C20 1.78(18) . . . . ?
S1 C18 C19 C20 -173.89(10) . . . . ?
C18 C19 C20 C21 0.57(18) . . . . ?
C19 C20 C21 C22 -2.55(18) . . . . ?
C19 C20 C21 C24 175.61(11) . . . . ?
C20 C21 C22 C23 2.26(17) . . . . ?
C24 C21 C22 C23 -175.91(11) . . . . ?
C21 C22 C23 C18 0.00(17) . . . . ?
C19 C18 C23 C22 -2.08(17) . . . . ?
S1 C18 C23 C22 173.65(9) . . . . ?
C16 C15 C14 C13 -0.6(2) . . . . ?
C15 C14 C13 C12 1.03(19) . . . . ?
C14 C13 C12 C17 -0.48(18) . . . . ?
C14 C13 C12 C11 178.31(11) . . . . ?
C16 C17 C12 C13 -0.45(19) . . . . ?
C16 C17 C12 C11 -179.25(11) . . . . ?
C6 C5 C4 C3 1.22(17) . . . . ?
C13 C12 C11 C10 -138.49(12) . . . . ?
C17 C12 C11 C10 40.28(16) . . . . ?
C13 C12 C11 C8 38.60(17) . . . . ?
C17 C12 C11 C8 -142.63(12) . . . . ?
C5 C4 C3 C2 -0.39(18) . . . . ?
C4 C3 C2 C1 -0.67(17) . . . . ?
C19 C18 S1 O3 154.26(10) . . . . ?
C23 C18 S1 O3 -21.56(11) . . . . ?
C19 C18 S1 O2 19.83(11) . . . . ?
C23 C18 S1 O2 -155.99(9) . . . . ?
C19 C18 S1 N1 -93.40(10) . . . . ?
C23 C18 S1 N1 90.78(10) . . . . ?
C5 C6 C1 C2 -0.07(16) . . . . ?
C7 C6 C1 C2 177.56(10) . . . . ?
C3 C2 C1 C6 0.89(16) . . . . ?
O3 S1 N1 C9 -138.18(10) . . . . ?
O2 S1 N1 C9 -8.99(11) . . . . ?
C18 S1 N1 C9 107.27(10) . . . . ?
O3 S1 N1 C10 43.78(11) . . . . ?
O2 S1 N1 C10 172.97(10) . . . . ?
C18 S1 N1 C10 -70.77(11) . . . . ?
C8 C11 C10 N1 1.26(12) . . . . ?
C12 C11 C10 N1 178.90(10) . . . . ?
C9 N1 C10 C11 -0.72(13) . . . . ?
S1 N1 C10 C11 177.59(8) . . . . ?
C10 N1 C9 C8 -0.16(13) . . . . ?
S1 N1 C9 C8 -178.45(8) . . . . ?
N1 C9 C8 C11 0.92(12) . . . . ?
N1 C9 C8 C7 172.67(10) . . . . ?
C10 C11 C8 C9 -1.36(12) . . . . ?
C12 C11 C8 C9 -178.83(11) . . . . ?
C10 C11 C8 C7 -172.57(11) . . . . ?
C12 C11 C8 C7 9.97(18) . . . . ?
C9 C8 C7 O1 -146.99(12) . . . . ?
C11 C8 C7 O1 22.95(18) . . . . ?
C9 C8 C7 C6 29.25(16) . . . . ?
C11 C8 C7 C6 -160.82(10) . . . . ?
C1 C6 C7 O1 -145.27(12) . . . . ?
C5 C6 C7 O1 32.41(16) . . . . ?
C1 C6 C7 C8 38.43(15) . . . . ?
C5 C6 C7 C8 -143.88(11) . . . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        60.60
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.032
