# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_171001c
_database_code_depnum_ccdc_archive 'CCDC 2186305'
loop_
_audit_author_name
_audit_author_address
'shuguang zhou'
;Xi An
China
;
_audit_update_record             
;
2022-07-08 deposited with the CCDC.	2023-11-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H19 N O3 S'
_chemical_formula_weight         353.42

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'
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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   27.711(2)
_cell_length_b                   9.4240(9)
_cell_length_c                   16.1661(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 123.253(3)
_cell_angle_gamma                90.00
_cell_volume                     3530.4(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2182
_cell_measurement_theta_min      2.333
_cell_measurement_theta_max      28.24

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1488
_exptl_absorpt_coefficient_mu    0.202
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9182
_exptl_absorpt_correction_T_max  0.9588
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8589
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_sigmaI/netI    0.0415
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.33
_diffrn_reflns_theta_max         25.02
_reflns_number_total             3118
_reflns_number_gt                2029
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0403P)²+2.8634P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3118
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0788
_refine_ls_R_factor_gt           0.0417
_refine_ls_wR_factor_ref         0.1092
_refine_ls_wR_factor_gt          0.0923
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.18013(3) 0.35834(7) 0.72869(4) 0.0372(2) Uani 1 1 d . . .
N1 N 0.20301(9) 0.4585(2) 0.51570(14) 0.0387(5) Uani 1 1 d . . .
O1 O 0.08688(8) 0.0496(2) 0.39393(13) 0.0589(6) Uani 1 1 d . . .
O2 O 0.20476(7) 0.2285(2) 0.78284(12) 0.0485(5) Uani 1 1 d . . .
O3 O 0.20618(8) 0.4906(2) 0.77738(12) 0.0496(5) Uani 1 1 d . . .
C1 C 0.17410(10) 0.3544(3) 0.44624(16) 0.0347(6) Uani 1 1 d . . .
H1 H 0.1708 0.3627 0.3860 0.042 Uiso 1 1 calc R . .
C2 C 0.15018(10) 0.2408(3) 0.46075(16) 0.0335(6) Uani 1 1 d . . .
C3 C 0.15586(12) 0.2170(3) 0.55811(17) 0.0456(7) Uani 1 1 d . . .
H3A H 0.1185 0.1934 0.5462 0.055 Uiso 1 1 calc R . .
H3B H 0.1819 0.1383 0.5929 0.055 Uiso 1 1 calc R . .
C4 C 0.17890(10) 0.3493(3) 0.62016(16) 0.0319(6) Uani 1 1 d . . .
C5 C 0.20143(10) 0.4568(3) 0.59943(16) 0.0346(6) Uani 1 1 d . . .
H5 H 0.2166 0.5335 0.6427 0.042 Uiso 1 1 calc R . .
C6 C 0.22819(13) 0.5792(3) 0.4960(2) 0.0607(9) Uani 1 1 d . . .
H6A H 0.2448 0.5476 0.4604 0.091 Uiso 1 1 calc R . .
H6B H 0.2577 0.6213 0.5574 0.091 Uiso 1 1 calc R . .
H6C H 0.1987 0.6481 0.4571 0.091 Uiso 1 1 calc R . .
C7 C 0.11472(10) 0.1400(3) 0.38236(17) 0.0373(6) Uani 1 1 d . . .
C8 C 0.10927(10) 0.1435(2) 0.28444(17) 0.0330(6) Uani 1 1 d . . .
C9 C 0.15631(11) 0.1484(3) 0.27642(19) 0.0437(7) Uani 1 1 d . . .
H9 H 0.1931 0.1595 0.3329 0.052 Uiso 1 1 calc R . .
C10 C 0.14909(12) 0.1370(3) 0.1849(2) 0.0506(7) Uani 1 1 d . . .
H10 H 0.1811 0.1374 0.1804 0.061 Uiso 1 1 calc R . .
C11 C 0.09483(13) 0.1251(3) 0.1011(2) 0.0519(8) Uani 1 1 d . . .
H11 H 0.0900 0.1171 0.0396 0.062 Uiso 1 1 calc R . .
C12 C 0.04771(12) 0.1248(3) 0.10762(18) 0.0475(7) Uani 1 1 d . . .
H12 H 0.0109 0.1198 0.0504 0.057 Uiso 1 1 calc R . .
C13 C 0.05454(11) 0.1321(3) 0.19867(17) 0.0396(6) Uani 1 1 d . . .
H13 H 0.0223 0.1294 0.2026 0.048 Uiso 1 1 calc R . .
C14 C 0.10714(10) 0.3615(3) 0.68990(16) 0.0350(6) Uani 1 1 d . . .
C15 C 0.07661(12) 0.4880(3) 0.6584(2) 0.0499(7) Uani 1 1 d . . .
H15 H 0.0946 0.5709 0.6577 0.060 Uiso 1 1 calc R . .
C16 C 0.01984(13) 0.4896(3) 0.6284(2) 0.0544(8) Uani 1 1 d . . .
H16 H -0.0005 0.5746 0.6072 0.065 Uiso 1 1 calc R . .
C17 C -0.00803(11) 0.3683(3) 0.62879(18) 0.0455(7) Uani 1 1 d . . .
C18 C 0.02276(11) 0.2432(3) 0.6601(2) 0.0468(7) Uani 1 1 d . . .
H18 H 0.0047 0.1605 0.6609 0.056 Uiso 1 1 calc R . .
C19 C 0.08012(11) 0.2386(3) 0.69050(18) 0.0426(7) Uani 1 1 d . . .
H19 H 0.1004 0.1535 0.7112 0.051 Uiso 1 1 calc R . .
C20 C -0.07079(12) 0.3740(3) 0.5953(2) 0.0667(9) Uani 1 1 d . . .
H20A H -0.0943 0.3939 0.5257 0.100 Uiso 1 1 calc R . .
H20B H -0.0760 0.4475 0.6308 0.100 Uiso 1 1 calc R . .
H20C H -0.0819 0.2844 0.6082 0.100 Uiso 1 1 calc R . .


_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 O3 1.4395(18) . ?
S1 O2 1.4404(18) . ?
S1 C4 1.738(2) . ?
S1 C14 1.759(2) . ?
N1 C1 1.371(3) . ?
N1 C5 1.378(3) . ?
N1 C6 1.458(3) . ?
O1 C7 1.230(3) . ?
C1 C2 1.346(3) . ?
C1 H1 0.9300 . ?
C2 C7 1.452(3) . ?
C2 C3 1.510(3) . ?
C3 C4 1.505(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.326(3) . ?
C5 H5 0.9300 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C8 1.506(3) . ?
C8 C9 1.380(3) . ?
C8 C13 1.388(3) . ?
C9 C10 1.384(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.370(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.367(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.379(3) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C19 1.382(3) . ?
C14 C15 1.387(3) . ?
C15 C16 1.369(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.381(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.379(4) . ?
C17 C20 1.513(4) . ?
C18 C19 1.383(3) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?

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
O3 S1 O2 118.37(11) . . ?
O3 S1 C4 108.71(11) . . ?
O2 S1 C4 108.20(11) . . ?
O3 S1 C14 108.32(11) . . ?
O2 S1 C14 107.45(11) . . ?
C4 S1 C14 105.00(11) . . ?
C1 N1 C5 118.5(2) . . ?
C1 N1 C6 120.9(2) . . ?
C5 N1 C6 120.1(2) . . ?
C2 C1 N1 123.3(2) . . ?
C2 C1 H1 118.3 . . ?
N1 C1 H1 118.3 . . ?
C1 C2 C7 122.0(2) . . ?
C1 C2 C3 121.3(2) . . ?
C7 C2 C3 116.5(2) . . ?
C4 C3 C2 109.6(2) . . ?
C4 C3 H3A 109.8 . . ?
C2 C3 H3A 109.8 . . ?
C4 C3 H3B 109.8 . . ?
C2 C3 H3B 109.8 . . ?
H3A C3 H3B 108.2 . . ?
C5 C4 C3 123.4(2) . . ?
C5 C4 S1 117.79(18) . . ?
C3 C4 S1 118.67(17) . . ?
C4 C5 N1 122.0(2) . . ?
C4 C5 H5 119.0 . . ?
N1 C5 H5 119.0 . . ?
N1 C6 H6A 109.5 . . ?
N1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O1 C7 C2 120.0(2) . . ?
O1 C7 C8 117.7(2) . . ?
C2 C7 C8 122.2(2) . . ?
C9 C8 C13 118.7(2) . . ?
C9 C8 C7 123.0(2) . . ?
C13 C8 C7 118.2(2) . . ?
C8 C9 C10 120.5(2) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C11 C10 C9 120.1(3) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C12 C11 C10 120.0(2) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C13 120.3(2) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C12 C13 C8 120.4(2) . . ?
C12 C13 H13 119.8 . . ?
C8 C13 H13 119.8 . . ?
C19 C14 C15 119.9(2) . . ?
C19 C14 S1 120.34(19) . . ?
C15 C14 S1 119.7(2) . . ?
C16 C15 C14 119.4(3) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
C15 C16 C17 121.7(3) . . ?
C15 C16 H16 119.1 . . ?
C17 C16 H16 119.1 . . ?
C18 C17 C16 118.3(2) . . ?
C18 C17 C20 121.4(3) . . ?
C16 C17 C20 120.3(3) . . ?
C17 C18 C19 121.1(3) . . ?
C17 C18 H18 119.5 . . ?
C19 C18 H18 119.5 . . ?
C14 C19 C18 119.6(2) . . ?
C14 C19 H19 120.2 . . ?
C18 C19 H19 120.2 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
C5 N1 C1 C2 -8.5(4) . . . . ?
C6 N1 C1 C2 179.9(3) . . . . ?
N1 C1 C2 C7 173.4(2) . . . . ?
N1 C1 C2 C3 -2.6(4) . . . . ?
C1 C2 C3 C4 12.2(3) . . . . ?
C7 C2 C3 C4 -164.0(2) . . . . ?
C2 C3 C4 C5 -12.7(3) . . . . ?
C2 C3 C4 S1 171.26(17) . . . . ?
O3 S1 C4 C5 1.0(2) . . . . ?
O2 S1 C4 C5 -128.7(2) . . . . ?
C14 S1 C4 C5 116.8(2) . . . . ?
O3 S1 C4 C3 177.34(19) . . . . ?
O2 S1 C4 C3 47.6(2) . . . . ?
C14 S1 C4 C3 -66.9(2) . . . . ?
C3 C4 C5 N1 3.2(4) . . . . ?
S1 C4 C5 N1 179.27(18) . . . . ?
C1 N1 C5 C4 8.2(3) . . . . ?
C6 N1 C5 C4 180.0(3) . . . . ?
C1 C2 C7 O1 -169.5(3) . . . . ?
C3 C2 C7 O1 6.8(4) . . . . ?
C1 C2 C7 C8 9.0(4) . . . . ?
C3 C2 C7 C8 -174.8(2) . . . . ?
O1 C7 C8 C9 -131.1(3) . . . . ?
C2 C7 C8 C9 50.4(4) . . . . ?
O1 C7 C8 C13 44.7(3) . . . . ?
C2 C7 C8 C13 -133.8(2) . . . . ?
C13 C8 C9 C10 -2.4(4) . . . . ?
C7 C8 C9 C10 173.4(2) . . . . ?
C8 C9 C10 C11 2.0(4) . . . . ?
C9 C10 C11 C12 0.2(4) . . . . ?
C10 C11 C12 C13 -2.0(4) . . . . ?
C11 C12 C13 C8 1.7(4) . . . . ?
C9 C8 C13 C12 0.5(4) . . . . ?
C7 C8 C13 C12 -175.5(2) . . . . ?
O3 S1 C14 C19 -145.40(19) . . . . ?
O2 S1 C14 C19 -16.4(2) . . . . ?
C4 S1 C14 C19 98.6(2) . . . . ?
O3 S1 C14 C15 34.7(2) . . . . ?
O2 S1 C14 C15 163.7(2) . . . . ?
C4 S1 C14 C15 -81.3(2) . . . . ?
C19 C14 C15 C16 0.1(4) . . . . ?
S1 C14 C15 C16 -180.0(2) . . . . ?
C14 C15 C16 C17 0.2(4) . . . . ?
C15 C16 C17 C18 -0.2(4) . . . . ?
C15 C16 C17 C20 179.9(3) . . . . ?
C16 C17 C18 C19 0.0(4) . . . . ?
C20 C17 C18 C19 179.9(2) . . . . ?
C15 C14 C19 C18 -0.4(4) . . . . ?
S1 C14 C19 C18 179.73(19) . . . . ?
C17 C18 C19 C14 0.3(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.047
