# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_b
_database_code_depnum_ccdc_archive 'CCDC 2310727'
loop_
_audit_author_name
_audit_author_address
'Bo Jiang'
;Jiangsu Normal University
China
;
_audit_update_record             
;
2023-11-28 deposited with the CCDC.	2024-01-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H30 N2 O3 S'
_chemical_formula_weight         462.59

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           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   9.7941(9)
_cell_length_b                   11.2385(11)
_cell_length_c                   23.348(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2569.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9988
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      32.36

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.196
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             984
_exptl_absorpt_coefficient_mu    0.155
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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            42129
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_av_sigmaI/netI    0.0376
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         2.52
_diffrn_reflns_theta_max         35.08
_reflns_number_total             11291
_reflns_number_gt                8080
_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)+(0.1038P)²+0.2838P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.05(7)
_refine_ls_number_reflns         11291
_refine_ls_number_parameters     304
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0959
_refine_ls_R_factor_gt           0.0630
_refine_ls_wR_factor_ref         0.1919
_refine_ls_wR_factor_gt          0.1617
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.021
_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 0.06909(5) 0.52496(4) 0.14717(2) 0.04756(13) Uani 1 1 d . . .
C16 C 0.08112(17) 0.90198(15) 0.03971(7) 0.0361(3) Uani 1 1 d . . .
N2 N 0.06830(15) 0.77645(12) 0.18270(6) 0.0362(3) Uani 1 1 d . . .
N1 N 0.19724(15) 0.59727(12) 0.17717(6) 0.0379(3) Uani 1 1 d . . .
C14 C 0.03609(15) 0.83714(14) 0.13772(6) 0.0336(3) Uani 1 1 d . . .
C18 C -0.12574(16) 0.98022(15) 0.09769(7) 0.0367(3) Uani 1 1 d . . .
C19 C -0.08613(16) 0.91095(15) 0.14084(7) 0.0373(3) Uani 1 1 d . . .
H19 H -0.1382 0.9096 0.1741 0.045 Uiso 1 1 calc R . .
C1 C 0.18609(16) 0.70968(13) 0.18799(6) 0.0326(3) Uani 1 1 d . . .
C15 C 0.11707(16) 0.83703(15) 0.08548(7) 0.0350(3) Uani 1 1 d . . .
H15 H 0.1957 0.7908 0.0838 0.042 Uiso 1 1 calc R . .
C8 C 0.13784(19) 0.38052(15) 0.14640(8) 0.0401(3) Uani 1 1 d . . .
C2 C 0.30369(18) 0.77010(14) 0.21518(7) 0.0358(3) Uani 1 1 d . . .
C24 C 0.1645(2) 0.90164(18) -0.01556(8) 0.0470(4) Uani 1 1 d . . .
C17 C -0.04580(19) 0.9749(2) 0.04322(8) 0.0484(4) Uani 1 1 d . . .
C7 C 0.4333(2) 0.72261(19) 0.20909(10) 0.0516(4) Uani 1 1 d . . .
H7 H 0.4462 0.6548 0.1869 0.062 Uiso 1 1 calc R . .
C20 C -0.2484(2) 1.06405(18) 0.10193(8) 0.0474(4) Uani 1 1 d . . .
C13 C 0.0991(2) 0.2986(2) 0.18737(9) 0.0520(5) Uani 1 1 d . . .
H13 H 0.0381 0.3194 0.2162 0.062 Uiso 1 1 calc R . .
O2 O 0.0530(2) 0.56410(17) 0.08943(9) 0.0753(6) Uani 1 1 d . . .
C3 C 0.2838(3) 0.87174(19) 0.24828(10) 0.0533(5) Uani 1 1 d . . .
H3 H 0.1973 0.9049 0.2520 0.064 Uiso 1 1 calc R . .
O3 O -0.0841(3) 1.0301(3) 0.00158(9) 0.1157(12) Uani 1 1 d . . .
O1 O -0.04725(18) 0.52600(18) 0.18430(12) 0.0836(7) Uani 1 1 d . . .
C9 C 0.2307(3) 0.3511(2) 0.10444(10) 0.0622(6) Uani 1 1 d . . .
H9 H 0.2569 0.4070 0.0772 0.075 Uiso 1 1 calc R . .
C5 C 0.5234(3) 0.8753(3) 0.26909(14) 0.0762(8) Uani 1 1 d . . .
H5 H 0.5973 0.9109 0.2873 0.091 Uiso 1 1 calc R . .
C6 C 0.5435(3) 0.7756(3) 0.23585(14) 0.0708(7) Uani 1 1 d . . .
H6 H 0.6307 0.7442 0.2314 0.085 Uiso 1 1 calc R . .
C11 C 0.2447(4) 0.1546(2) 0.14280(16) 0.0807(9) Uani 1 1 d . . .
H11 H 0.2798 0.0778 0.1414 0.097 Uiso 1 1 calc R . .
C12 C 0.1530(3) 0.1846(2) 0.18465(13) 0.0689(7) Uani 1 1 d . . .
H12 H 0.1265 0.1280 0.2115 0.083 Uiso 1 1 calc R . .
C4 C 0.3948(3) 0.9227(3) 0.27561(13) 0.0718(7) Uani 1 1 d . . .
H4 H 0.3823 0.9895 0.2985 0.086 Uiso 1 1 calc R . .
C25 C 0.2878(3) 0.8196(3) -0.01078(13) 0.0742(8) Uani 1 1 d . . .
H25A H 0.3449 0.8456 0.0202 0.111 Uiso 1 1 calc R . .
H25B H 0.3386 0.8218 -0.0459 0.111 Uiso 1 1 calc R . .
H25C H 0.2574 0.7398 -0.0036 0.111 Uiso 1 1 calc R . .
C22 C -0.3587(3) 1.0274(4) 0.05930(16) 0.0892(11) Uani 1 1 d . . .
H22A H -0.3926 0.9498 0.0692 0.134 Uiso 1 1 calc R . .
H22B H -0.3208 1.0254 0.0214 0.134 Uiso 1 1 calc R . .
H22C H -0.4323 1.0838 0.0605 0.134 Uiso 1 1 calc R . .
C27 C 0.0781(4) 0.8557(4) -0.06561(11) 0.0935(12) Uani 1 1 d . . .
H27A H 0.1317 0.8565 -0.1000 0.140 Uiso 1 1 calc R . .
H27B H -0.0003 0.9059 -0.0704 0.140 Uiso 1 1 calc R . .
H27C H 0.0488 0.7759 -0.0577 0.140 Uiso 1 1 calc R . .
C26 C 0.2176(4) 1.0266(2) -0.02827(15) 0.0855(10) Uani 1 1 d . . .
H26A H 0.2768 1.0518 0.0021 0.128 Uiso 1 1 calc R . .
H26B H 0.1419 1.0806 -0.0312 0.128 Uiso 1 1 calc R . .
H26C H 0.2672 1.0260 -0.0637 0.128 Uiso 1 1 calc R . .
C10 C 0.2848(4) 0.2365(3) 0.10327(14) 0.0828(9) Uani 1 1 d . . .
H10 H 0.3485 0.2159 0.0754 0.099 Uiso 1 1 calc R . .
C23 C -0.3094(5) 1.0623(5) 0.16099(13) 0.1156(18) Uani 1 1 d . . .
H23A H -0.3476 0.9852 0.1684 0.173 Uiso 1 1 calc R . .
H23B H -0.3798 1.1214 0.1635 0.173 Uiso 1 1 calc R . .
H23C H -0.2396 1.0791 0.1887 0.173 Uiso 1 1 calc R . .
C21 C -0.2026(5) 1.1911(3) 0.0876(3) 0.1151(16) Uani 1 1 d . . .
H21A H -0.2775 1.2449 0.0933 0.173 Uiso 1 1 calc R . .
H21B H -0.1733 1.1946 0.0485 0.173 Uiso 1 1 calc R . .
H21C H -0.1284 1.2132 0.1123 0.173 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 O2 1.4269(19) . ?
S1 O1 1.432(2) . ?
S1 N1 1.6511(15) . ?
S1 C8 1.7575(18) . ?
C16 C15 1.341(2) . ?
C16 C17 1.491(2) . ?
C16 C24 1.527(2) . ?
N2 C14 1.2915(18) . ?
N2 C1 1.382(2) . ?
N1 C1 1.293(2) . ?
C14 C15 1.455(2) . ?
C14 C19 1.458(2) . ?
C18 C19 1.331(2) . ?
C18 C17 1.495(2) . ?
C18 C20 1.530(2) . ?
C1 C2 1.480(2) . ?
C8 C9 1.377(3) . ?
C8 C13 1.381(3) . ?
C2 C7 1.384(3) . ?
C2 C3 1.393(3) . ?
C24 C25 1.523(3) . ?
C24 C26 1.527(3) . ?
C24 C27 1.533(4) . ?
C17 O3 1.213(2) . ?
C7 C6 1.383(3) . ?
C20 C23 1.503(4) . ?
C20 C22 1.526(3) . ?
C20 C21 1.533(4) . ?
C13 C12 1.387(4) . ?
C3 C4 1.384(3) . ?
C9 C10 1.393(4) . ?
C5 C4 1.376(5) . ?
C5 C6 1.377(5) . ?
C11 C10 1.361(5) . ?
C11 C12 1.369(5) . ?

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
O2 S1 O1 118.78(15) . . ?
O2 S1 N1 109.46(10) . . ?
O1 S1 N1 110.13(11) . . ?
O2 S1 C8 108.51(11) . . ?
O1 S1 C8 108.58(11) . . ?
N1 S1 C8 99.65(8) . . ?
C15 C16 C17 118.31(14) . . ?
C15 C16 C24 122.10(16) . . ?
C17 C16 C24 119.58(14) . . ?
C14 N2 C1 124.30(14) . . ?
C1 N1 S1 119.97(12) . . ?
N2 C14 C15 123.24(14) . . ?
N2 C14 C19 117.41(14) . . ?
C15 C14 C19 119.34(13) . . ?
C19 C18 C17 117.90(14) . . ?
C19 C18 C20 122.69(15) . . ?
C17 C18 C20 119.40(14) . . ?
C18 C19 C14 122.29(14) . . ?
N1 C1 N2 125.71(15) . . ?
N1 C1 C2 117.79(14) . . ?
N2 C1 C2 116.04(13) . . ?
C16 C15 C14 121.62(14) . . ?
C9 C8 C13 120.92(19) . . ?
C9 C8 S1 118.84(16) . . ?
C13 C8 S1 120.24(16) . . ?
C7 C2 C3 120.08(18) . . ?
C7 C2 C1 119.51(15) . . ?
C3 C2 C1 120.37(17) . . ?
C25 C24 C26 107.6(2) . . ?
C25 C24 C16 111.31(16) . . ?
C26 C24 C16 110.12(18) . . ?
C25 C24 C27 106.8(3) . . ?
C26 C24 C27 110.5(3) . . ?
C16 C24 C27 110.5(2) . . ?
O3 C17 C16 119.68(18) . . ?
O3 C17 C18 119.97(18) . . ?
C16 C17 C18 120.36(14) . . ?
C6 C7 C2 120.2(2) . . ?
C23 C20 C22 108.3(3) . . ?
C23 C20 C18 111.29(17) . . ?
C22 C20 C18 110.34(18) . . ?
C23 C20 C21 109.2(3) . . ?
C22 C20 C21 108.5(3) . . ?
C18 C20 C21 109.2(2) . . ?
C8 C13 C12 118.7(2) . . ?
C4 C3 C2 119.1(2) . . ?
C8 C9 C10 119.2(3) . . ?
C4 C5 C6 120.6(2) . . ?
C5 C6 C7 119.6(3) . . ?
C10 C11 C12 120.5(3) . . ?
C11 C12 C13 120.6(2) . . ?
C5 C4 C3 120.5(2) . . ?
C11 C10 C9 120.1(3) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        35.08
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.378
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.080
