# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_a
_database_code_depnum_ccdc_archive 'CCDC 2348540'
loop_
_audit_author_name
_audit_author_address
'xie xiaofei'
;Nanjing Agricultural University
China
;
_audit_update_record             
;
2024-04-16 deposited with the CCDC.	2024-07-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H27 N O2 S'
_chemical_formula_weight         417.55

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   'P2(1)/c  '

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

_cell_length_a                   5.799(4)
_cell_length_b                   17.937(12)
_cell_length_c                   22.300(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.399(13)
_cell_angle_gamma                90.00
_cell_volume                     2300(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1099
_cell_measurement_theta_min      2.99
_cell_measurement_theta_max      19.53

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.206
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             888
_exptl_absorpt_coefficient_mu    0.162
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9545
_exptl_absorpt_correction_T_max  0.9652
_exptl_absorpt_process_details   SADABS

_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11208
_diffrn_reflns_av_R_equivalents  0.0648
_diffrn_reflns_av_sigmaI/netI    0.0834
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.46
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4033
_reflns_number_gt                2143
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0520P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4033
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1164
_refine_ls_R_factor_gt           0.0552
_refine_ls_wR_factor_ref         0.1376
_refine_ls_wR_factor_gt          0.1200
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_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
N1 N 0.9958(6) 0.55193(18) 0.43296(15) 0.0922(10) Uani 1 1 d . . .
S1 S 0.99552(14) 0.88570(4) 0.38607(3) 0.0504(3) Uani 1 1 d . . .
O1 O 1.2204(3) 0.85931(11) 0.37592(9) 0.0619(6) Uani 1 1 d . . .
O2 O 0.9767(4) 0.92639(10) 0.44013(8) 0.0647(6) Uani 1 1 d . . .
C1 C 0.6517(5) 0.67141(14) 0.14703(13) 0.0468(7) Uani 1 1 d . . .
C2 C 0.8138(6) 0.62742(18) 0.12545(14) 0.0676(10) Uani 1 1 d . . .
H2A H 0.9576 0.6207 0.1485 0.081 Uiso 1 1 calc R . .
C3 C 0.7688(7) 0.59247(18) 0.06980(16) 0.0777(11) Uani 1 1 d . . .
H3A H 0.8816 0.5622 0.0563 0.093 Uiso 1 1 calc R . .
C4 C 0.5626(8) 0.60200(18) 0.03498(15) 0.0728(10) Uani 1 1 d . . .
H4A H 0.5337 0.5789 -0.0026 0.087 Uiso 1 1 calc R . .
C5 C 0.4010(7) 0.6448(2) 0.05502(16) 0.0884(12) Uani 1 1 d . . .
H5A H 0.2582 0.6511 0.0313 0.106 Uiso 1 1 calc R . .
C6 C 0.4427(6) 0.6798(2) 0.11040(14) 0.0769(11) Uani 1 1 d . . .
H6A H 0.3276 0.7097 0.1233 0.092 Uiso 1 1 calc R . .
C7 C 0.6924(5) 0.70678(14) 0.20767(12) 0.0443(7) Uani 1 1 d . . .
C8 C 0.5307(6) 0.75246(19) 0.22861(14) 0.0706(10) Uani 1 1 d . . .
H8A H 0.3930 0.7627 0.2037 0.085 Uiso 1 1 calc R . .
C9 C 0.5663(6) 0.78351(18) 0.28525(14) 0.0672(10) Uani 1 1 d . . .
H9A H 0.4518 0.8139 0.2978 0.081 Uiso 1 1 calc R . .
C10 C 0.7644(5) 0.77101(15) 0.32355(13) 0.0449(7) Uani 1 1 d . . .
C11 C 0.9271(6) 0.72526(18) 0.30373(14) 0.0693(10) Uani 1 1 d . . .
H11A H 1.0641 0.7152 0.3290 0.083 Uiso 1 1 calc R . .
C12 C 0.8921(6) 0.69389(18) 0.24729(14) 0.0666(10) Uani 1 1 d . . .
H12A H 1.0062 0.6629 0.2352 0.080 Uiso 1 1 calc R . .
C13 C 0.7989(5) 0.80779(15) 0.38486(12) 0.0471(8) Uani 1 1 d . . .
H13A H 0.6477 0.8274 0.3925 0.057 Uiso 1 1 calc R . .
C14 C 0.8779(5) 0.93937(14) 0.32392(12) 0.0473(7) Uani 1 1 d . . .
C15 C 0.6826(6) 0.98104(16) 0.32746(14) 0.0594(9) Uani 1 1 d . . .
H15A H 0.6170 0.9830 0.3634 0.071 Uiso 1 1 calc R . .
C16 C 0.5844(6) 1.01977(17) 0.27784(16) 0.0658(9) Uani 1 1 d . . .
H16A H 0.4493 1.0470 0.2801 0.079 Uiso 1 1 calc R . .
C17 C 0.6800(6) 1.01940(18) 0.22492(15) 0.0641(9) Uani 1 1 d . . .
C18 C 0.8775(7) 0.97897(19) 0.22242(14) 0.0741(10) Uani 1 1 d . . .
H18A H 0.9461 0.9787 0.1870 0.089 Uiso 1 1 calc R . .
C19 C 0.9779(6) 0.93822(17) 0.27185(14) 0.0640(9) Uani 1 1 d . . .
H19A H 1.1119 0.9104 0.2695 0.077 Uiso 1 1 calc R . .
C20 C 0.5668(7) 1.0627(2) 0.17069(15) 0.0985(14) Uani 1 1 d . . .
H20A H 0.4314 1.0880 0.1811 0.148 Uiso 1 1 calc R . .
H20B H 0.5221 1.0290 0.1378 0.148 Uiso 1 1 calc R . .
H20C H 0.6749 1.0987 0.1588 0.148 Uiso 1 1 calc R . .
C21 C 0.8874(6) 0.75716(16) 0.43775(13) 0.0561(8) Uani 1 1 d . . .
H21A H 1.0121 0.7262 0.4265 0.067 Uiso 1 1 calc R . .
H21B H 0.9501 0.7875 0.4720 0.067 Uiso 1 1 calc R . .
C22 C 0.6956(5) 0.70756(15) 0.45608(13) 0.0564(8) Uani 1 1 d . . .
H22A H 0.6068 0.6875 0.4198 0.068 Uiso 1 1 calc R . .
H22B H 0.5911 0.7379 0.4765 0.068 Uiso 1 1 calc R . .
C23 C 0.7827(6) 0.64279(16) 0.49749(13) 0.0544(8) Uani 1 1 d . . .
C24 C 0.5780(6) 0.60218(18) 0.51776(16) 0.0810(11) Uani 1 1 d . . .
H24A H 0.4744 0.5865 0.4830 0.121 Uiso 1 1 calc R . .
H24B H 0.4972 0.6349 0.5420 0.121 Uiso 1 1 calc R . .
H24C H 0.6325 0.5593 0.5412 0.121 Uiso 1 1 calc R . .
C25 C 0.9508(6) 0.66818(18) 0.55264(13) 0.0755(11) Uani 1 1 d . . .
H25A H 1.0014 0.6256 0.5770 0.113 Uiso 1 1 calc R . .
H25B H 0.8729 0.7026 0.5762 0.113 Uiso 1 1 calc R . .
H25C H 1.0830 0.6921 0.5392 0.113 Uiso 1 1 calc R . .
C26 C 0.9050(6) 0.59138(19) 0.46169(15) 0.0630(9) 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
N1 C26 1.129(4) . ?
S1 O2 1.425(2) . ?
S1 O1 1.432(2) . ?
S1 C14 1.752(3) . ?
S1 C13 1.802(3) . ?
C1 C2 1.362(4) . ?
C1 C6 1.380(4) . ?
C1 C7 1.485(4) . ?
C2 C3 1.385(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.350(5) . ?
C3 H3A 0.9300 . ?
C4 C5 1.332(5) . ?
C4 H4A 0.9300 . ?
C5 C6 1.379(4) . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9300 . ?
C7 C8 1.372(4) . ?
C7 C12 1.382(4) . ?
C8 C9 1.371(4) . ?
C8 H8A 0.9300 . ?
C9 C10 1.359(4) . ?
C9 H9A 0.9300 . ?
C10 C11 1.366(4) . ?
C10 C13 1.508(4) . ?
C11 C12 1.370(4) . ?
C11 H11A 0.9300 . ?
C12 H12A 0.9300 . ?
C13 C21 1.524(4) . ?
C13 H13A 0.9800 . ?
C14 C19 1.363(4) . ?
C14 C15 1.368(4) . ?
C15 C16 1.367(4) . ?
C15 H15A 0.9300 . ?
C16 C17 1.367(4) . ?
C16 H16A 0.9300 . ?
C17 C18 1.363(5) . ?
C17 C20 1.514(4) . ?
C18 C19 1.387(4) . ?
C18 H18A 0.9300 . ?
C19 H19A 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C22 1.521(4) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 C23 1.529(4) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C26 1.462(5) . ?
C23 C24 1.510(4) . ?
C23 C25 1.536(4) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 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
O2 S1 O1 118.25(13) . . ?
O2 S1 C14 108.86(14) . . ?
O1 S1 C14 109.03(14) . . ?
O2 S1 C13 107.02(13) . . ?
O1 S1 C13 109.18(14) . . ?
C14 S1 C13 103.48(13) . . ?
C2 C1 C6 116.6(3) . . ?
C2 C1 C7 122.2(3) . . ?
C6 C1 C7 121.1(3) . . ?
C1 C2 C3 121.3(3) . . ?
C1 C2 H2A 119.3 . . ?
C3 C2 H2A 119.3 . . ?
C4 C3 C2 120.6(3) . . ?
C4 C3 H3A 119.7 . . ?
C2 C3 H3A 119.7 . . ?
C5 C4 C3 119.3(3) . . ?
C5 C4 H4A 120.4 . . ?
C3 C4 H4A 120.4 . . ?
C4 C5 C6 120.9(3) . . ?
C4 C5 H5A 119.6 . . ?
C6 C5 H5A 119.6 . . ?
C5 C6 C1 121.3(3) . . ?
C5 C6 H6A 119.3 . . ?
C1 C6 H6A 119.3 . . ?
C8 C7 C12 115.8(3) . . ?
C8 C7 C1 122.0(3) . . ?
C12 C7 C1 122.2(3) . . ?
C9 C8 C7 121.8(3) . . ?
C9 C8 H8A 119.1 . . ?
C7 C8 H8A 119.1 . . ?
C10 C9 C8 121.8(3) . . ?
C10 C9 H9A 119.1 . . ?
C8 C9 H9A 119.1 . . ?
C9 C10 C11 117.3(3) . . ?
C9 C10 C13 120.0(3) . . ?
C11 C10 C13 122.7(3) . . ?
C10 C11 C12 121.1(3) . . ?
C10 C11 H11A 119.4 . . ?
C12 C11 H11A 119.4 . . ?
C11 C12 C7 122.1(3) . . ?
C11 C12 H12A 118.9 . . ?
C7 C12 H12A 118.9 . . ?
C10 C13 C21 115.7(2) . . ?
C10 C13 S1 111.28(19) . . ?
C21 C13 S1 107.53(19) . . ?
C10 C13 H13A 107.3 . . ?
C21 C13 H13A 107.3 . . ?
S1 C13 H13A 107.3 . . ?
C19 C14 C15 120.3(3) . . ?
C19 C14 S1 120.0(3) . . ?
C15 C14 S1 119.7(2) . . ?
C16 C15 C14 119.5(3) . . ?
C16 C15 H15A 120.2 . . ?
C14 C15 H15A 120.2 . . ?
C15 C16 C17 121.6(3) . . ?
C15 C16 H16A 119.2 . . ?
C17 C16 H16A 119.2 . . ?
C18 C17 C16 118.3(3) . . ?
C18 C17 C20 121.4(3) . . ?
C16 C17 C20 120.3(3) . . ?
C17 C18 C19 121.1(3) . . ?
C17 C18 H18A 119.4 . . ?
C19 C18 H18A 119.4 . . ?
C14 C19 C18 119.2(3) . . ?
C14 C19 H19A 120.4 . . ?
C18 C19 H19A 120.4 . . ?
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 . . ?
C22 C21 C13 111.8(3) . . ?
C22 C21 H21A 109.3 . . ?
C13 C21 H21A 109.3 . . ?
C22 C21 H21B 109.3 . . ?
C13 C21 H21B 109.3 . . ?
H21A C21 H21B 107.9 . . ?
C21 C22 C23 114.2(3) . . ?
C21 C22 H22A 108.7 . . ?
C23 C22 H22A 108.7 . . ?
C21 C22 H22B 108.7 . . ?
C23 C22 H22B 108.7 . . ?
H22A C22 H22B 107.6 . . ?
C26 C23 C24 108.3(3) . . ?
C26 C23 C22 107.2(3) . . ?
C24 C23 C22 109.6(3) . . ?
C26 C23 C25 108.8(3) . . ?
C24 C23 C25 110.2(3) . . ?
C22 C23 C25 112.6(2) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
N1 C26 C23 178.5(4) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.046
