# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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_1
_database_code_depnum_ccdc_archive 'CCDC 2261040'
loop_
_audit_author_name
_audit_author_address
'Yongbo Fan'
;wuyi university
China
;
_audit_update_record             
;
2023-05-06 deposited with the CCDC.	2023-09-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H24 N2 O2 S'
_chemical_formula_weight         416.52

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   27.15(5)
_cell_length_b                   9.961(16)
_cell_length_c                   8.810(15)
_cell_angle_alpha                90
_cell_angle_beta                 90.85(4)
_cell_angle_gamma                90
_cell_volume                     2382(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5509
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      20.03

_exptl_crystal_description       Block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.161
_exptl_crystal_F_000             880
_exptl_transmission_factor_min   0.864
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.158
_shelx_estimated_absorpt_T_min   0.969
_shelx_estimated_absorpt_T_max   0.969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ccd
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            42862
_diffrn_reflns_av_unetI/netI     0.0758
_diffrn_reflns_av_R_equivalents  0.1075
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.251
_diffrn_reflns_theta_max         24.746
_diffrn_reflns_theta_full        24.746
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4065
_reflns_number_gt                2095
_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    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0523P)²+2.8722P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4065
_refine_ls_number_parameters     272
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1734
_refine_ls_R_factor_gt           0.0789
_refine_ls_wR_factor_ref         0.1893
_refine_ls_wR_factor_gt          0.1554
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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_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
C1 C 0.9223(2) 0.4091(6) 0.7652(7) 0.0950(18) Uani 1 1 d . . . . .
H1 H 0.9381 0.3892 0.6752 0.114 Uiso 1 1 calc R U . . .
C2 C 0.9461(3) 0.3843(7) 0.9056(9) 0.111(2) Uani 1 1 d . . . . .
H2 H 0.9774 0.3462 0.9073 0.133 Uiso 1 1 calc R U . . .
C3 C 0.9240(3) 0.4154(7) 1.0384(8) 0.108(2) Uani 1 1 d . . . . .
H3 H 0.9405 0.4006 1.1302 0.130 Uiso 1 1 calc R U . . .
C4 C 0.8774(3) 0.4686(6) 1.0372(7) 0.0952(19) Uani 1 1 d . . . . .
H4 H 0.8618 0.4880 1.1279 0.114 Uiso 1 1 calc R U . . .
C5 C 0.8535(2) 0.4934(6) 0.8980(6) 0.0848(16) Uani 1 1 d . . . . .
H5 H 0.8222 0.5313 0.8978 0.102 Uiso 1 1 calc R U . . .
C6 C 0.87508(18) 0.4634(5) 0.7609(6) 0.0681(14) Uani 1 1 d . . . . .
C7 C 0.84860(17) 0.4910(5) 0.6100(5) 0.0655(13) Uani 1 1 d . . . . .
H7 H 0.8264 0.5676 0.6228 0.079 Uiso 1 1 calc R U . . .
C8 C 0.81819(17) 0.3689(5) 0.5601(5) 0.0687(14) Uani 1 1 d . . . . .
H8A H 0.7975 0.3417 0.6434 0.082 Uiso 1 1 calc R U . . .
H8B H 0.8405 0.2953 0.5392 0.082 Uiso 1 1 calc R U . . .
C9 C 0.72746(15) 0.4862(4) 0.4617(5) 0.0500(11) Uani 1 1 d . . . . .
C10 C 0.71816(17) 0.5135(5) 0.6147(5) 0.0642(13) Uani 1 1 d . . . . .
H10 H 0.7407 0.4865 0.6892 0.077 Uiso 1 1 calc R U . . .
C11 C 0.67586(19) 0.5799(5) 0.6554(5) 0.0726(15) Uani 1 1 d . . . . .
H11 H 0.6704 0.5973 0.7576 0.087 Uiso 1 1 calc R U . . .
C12 C 0.64088(18) 0.6221(5) 0.5475(5) 0.0672(14) Uani 1 1 d . . . . .
H12 H 0.6123 0.6657 0.5772 0.081 Uiso 1 1 calc R U . . .
C13 C 0.64971(16) 0.5973(4) 0.3932(5) 0.0593(12) Uani 1 1 d . . . . .
H13 H 0.6270 0.6253 0.3196 0.071 Uiso 1 1 calc R U . . .
C14 C 0.69228(15) 0.5310(4) 0.3510(4) 0.0474(11) Uani 1 1 d . . . . .
C15 C 0.72827(17) 0.5960(6) 0.1129(6) 0.0777(16) Uani 1 1 d . . . . .
H15 H 0.7398 0.6718 0.1640 0.093 Uiso 1 1 calc R U . . .
C16 C 0.68804(17) 0.3761(5) 0.1237(5) 0.0751(15) Uani 1 1 d . . . . .
H16A H 0.6894 0.3081 0.2025 0.090 Uiso 1 1 calc R U . . .
H16B H 0.7127 0.3530 0.0495 0.090 Uiso 1 1 calc R U . . .
C17 C 0.63741(16) 0.3692(5) 0.0460(5) 0.0568(12) Uani 1 1 d . . . . .
C18 C 0.61120(16) 0.4808(5) -0.0019(5) 0.0623(13) Uani 1 1 d . . . . .
H18 H 0.6234 0.5660 0.0199 0.075 Uiso 1 1 calc R U . . .
C19 C 0.56672(17) 0.4678(6) -0.0826(5) 0.0683(13) Uani 1 1 d . . . . .
H19 H 0.5495 0.5442 -0.1131 0.082 Uiso 1 1 calc R U . . .
C20 C 0.54817(17) 0.3416(6) -0.1174(5) 0.0696(14) Uani 1 1 d . . . . .
C21 C 0.57356(19) 0.2288(6) -0.0661(6) 0.0886(17) Uani 1 1 d . . . . .
H21 H 0.5610 0.1434 -0.0850 0.106 Uiso 1 1 calc R U . . .
C22 C 0.61770(19) 0.2440(6) 0.0134(6) 0.0847(16) Uani 1 1 d . . . . .
H22 H 0.6346 0.1677 0.0458 0.102 Uiso 1 1 calc R U . . .
C23 C 0.5025(2) 0.3255(6) -0.2031(7) 0.0942(19) Uani 1 1 d . . . . .
C24 C 0.8978(3) 0.6590(6) 0.4885(8) 0.120(2) Uani 1 1 d . . . . .
H24A H 0.9059 0.6879 0.5910 0.144 Uiso 1 1 calc R U . . .
H24B H 0.8711 0.7150 0.4502 0.144 Uiso 1 1 calc R U . . .
C25 C 0.9409(3) 0.6738(7) 0.3915(8) 0.137(3) Uani 1 1 d . . . . .
H25A H 0.9660 0.6114 0.4235 0.205 Uiso 1 1 calc R U . . .
H25B H 0.9534 0.7637 0.3998 0.205 Uiso 1 1 calc R U . . .
H25C H 0.9316 0.6558 0.2880 0.205 Uiso 1 1 calc R U . . .
N1 N 0.70159(13) 0.5054(4) 0.1920(4) 0.0564(10) Uani 1 1 d . . . . .
N2 N 0.46687(18) 0.3105(6) -0.2713(7) 0.131(2) Uani 1 1 d . . . . .
O1 O 0.88239(12) 0.5209(4) 0.4899(4) 0.0813(10) Uani 1 1 d . . . . .
O2 O 0.73829(13) 0.5838(5) -0.0242(4) 0.1156(16) Uani 1 1 d . . . . .
S1 S 0.77929(4) 0.39733(14) 0.39285(14) 0.0686(4) 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
C1 C6 1.390(7) . ?
C1 C2 1.409(8) . ?
C1 H1 0.9300 . ?
C2 C3 1.358(9) . ?
C2 H2 0.9300 . ?
C3 C4 1.372(9) . ?
C3 H3 0.9300 . ?
C4 C5 1.401(8) . ?
C4 H4 0.9300 . ?
C5 C6 1.382(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.527(7) . ?
C7 O1 1.441(6) . ?
C7 C8 1.531(6) . ?
C7 H7 0.9800 . ?
C8 S1 1.822(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.402(6) . ?
C9 C14 1.427(6) . ?
C9 S1 1.776(5) . ?
C10 C11 1.378(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.398(7) . ?
C11 H11 0.9300 . ?
C12 C13 1.406(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.387(6) . ?
C13 H13 0.9300 . ?
C14 N1 1.450(5) . ?
C15 O2 1.249(6) . ?
C15 N1 1.356(6) . ?
C15 H15 0.9300 . ?
C16 N1 1.466(6) . ?
C16 C17 1.528(6) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.382(6) . ?
C17 C22 1.386(7) . ?
C18 C19 1.398(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.387(7) . ?
C19 H19 0.9300 . ?
C20 C21 1.390(7) . ?
C20 C23 1.450(7) . ?
C21 C22 1.387(7) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 N2 1.141(6) . ?
C24 O1 1.438(7) . ?
C24 C25 1.468(8) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
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
C6 C1 C2 120.2(6) . . ?
C6 C1 H1 119.9 . . ?
C2 C1 H1 119.9 . . ?
C3 C2 C1 120.8(6) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C2 C3 C4 120.1(6) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C5 119.3(6) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C6 C5 C4 122.1(6) . . ?
C6 C5 H5 119.0 . . ?
C4 C5 H5 119.0 . . ?
C5 C6 C1 117.5(5) . . ?
C5 C6 C7 121.5(5) . . ?
C1 C6 C7 121.0(5) . . ?
O1 C7 C6 112.3(4) . . ?
O1 C7 C8 107.4(4) . . ?
C6 C7 C8 110.6(4) . . ?
O1 C7 H7 108.8 . . ?
C6 C7 H7 108.8 . . ?
C8 C7 H7 108.8 . . ?
C7 C8 S1 114.4(3) . . ?
C7 C8 H8A 108.7 . . ?
S1 C8 H8A 108.7 . . ?
C7 C8 H8B 108.7 . . ?
S1 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
C10 C9 C14 117.9(4) . . ?
C10 C9 S1 125.5(3) . . ?
C14 C9 S1 116.6(3) . . ?
C11 C10 C9 120.4(4) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C12 121.8(4) . . ?
C10 C11 H11 119.1 . . ?
C12 C11 H11 119.1 . . ?
C11 C12 C13 118.8(4) . . ?
C11 C12 H12 120.6 . . ?
C13 C12 H12 120.6 . . ?
C14 C13 C12 119.9(4) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C13 C14 C9 121.2(4) . . ?
C13 C14 N1 120.1(4) . . ?
C9 C14 N1 118.7(4) . . ?
O2 C15 N1 123.9(6) . . ?
O2 C15 H15 118.1 . . ?
N1 C15 H15 118.1 . . ?
N1 C16 C17 116.2(4) . . ?
N1 C16 H16A 108.2 . . ?
C17 C16 H16A 108.2 . . ?
N1 C16 H16B 108.2 . . ?
C17 C16 H16B 108.2 . . ?
H16A C16 H16B 107.4 . . ?
C18 C17 C22 117.7(4) . . ?
C18 C17 C16 123.8(5) . . ?
C22 C17 C16 118.4(4) . . ?
C17 C18 C19 121.2(5) . . ?
C17 C18 H18 119.4 . . ?
C19 C18 H18 119.4 . . ?
C20 C19 C18 120.2(5) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C19 C20 C21 119.0(5) . . ?
C19 C20 C23 121.3(5) . . ?
C21 C20 C23 119.7(5) . . ?
C22 C21 C20 119.8(5) . . ?
C22 C21 H21 120.1 . . ?
C20 C21 H21 120.1 . . ?
C17 C22 C21 122.1(5) . . ?
C17 C22 H22 119.0 . . ?
C21 C22 H22 119.0 . . ?
N2 C23 C20 178.7(7) . . ?
O1 C24 C25 109.6(6) . . ?
O1 C24 H24A 109.8 . . ?
C25 C24 H24A 109.8 . . ?
O1 C24 H24B 109.8 . . ?
C25 C24 H24B 109.8 . . ?
H24A C24 H24B 108.2 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C15 N1 C14 118.7(4) . . ?
C15 N1 C16 120.5(4) . . ?
C14 N1 C16 120.3(4) . . ?
C24 O1 C7 113.1(4) . . ?
C9 S1 C8 104.7(2) . . ?

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
C6 C1 C2 C3 -1.4(10) . . . . ?
C1 C2 C3 C4 1.6(10) . . . . ?
C2 C3 C4 C5 -1.6(10) . . . . ?
C3 C4 C5 C6 1.3(9) . . . . ?
C4 C5 C6 C1 -1.1(8) . . . . ?
C4 C5 C6 C7 180.0(5) . . . . ?
C2 C1 C6 C5 1.1(8) . . . . ?
C2 C1 C6 C7 -180.0(5) . . . . ?
C5 C6 C7 O1 149.6(5) . . . . ?
C1 C6 C7 O1 -29.3(7) . . . . ?
C5 C6 C7 C8 -90.4(6) . . . . ?
C1 C6 C7 C8 90.7(6) . . . . ?
O1 C7 C8 S1 -64.0(4) . . . . ?
C6 C7 C8 S1 173.1(3) . . . . ?
C14 C9 C10 C11 0.9(7) . . . . ?
S1 C9 C10 C11 -178.0(4) . . . . ?
C9 C10 C11 C12 0.1(7) . . . . ?
C10 C11 C12 C13 -0.9(7) . . . . ?
C11 C12 C13 C14 0.6(7) . . . . ?
C12 C13 C14 C9 0.5(6) . . . . ?
C12 C13 C14 N1 -179.9(4) . . . . ?
C10 C9 C14 C13 -1.2(6) . . . . ?
S1 C9 C14 C13 177.8(3) . . . . ?
C10 C9 C14 N1 179.1(4) . . . . ?
S1 C9 C14 N1 -1.8(5) . . . . ?
N1 C16 C17 C18 19.7(7) . . . . ?
N1 C16 C17 C22 -164.2(4) . . . . ?
C22 C17 C18 C19 -1.0(7) . . . . ?
C16 C17 C18 C19 175.1(4) . . . . ?
C17 C18 C19 C20 -0.6(7) . . . . ?
C18 C19 C20 C21 2.3(7) . . . . ?
C18 C19 C20 C23 -179.0(5) . . . . ?
C19 C20 C21 C22 -2.5(8) . . . . ?
C23 C20 C21 C22 178.8(5) . . . . ?
C18 C17 C22 C21 0.8(8) . . . . ?
C16 C17 C22 C21 -175.5(5) . . . . ?
C20 C21 C22 C17 1.0(8) . . . . ?
O2 C15 N1 C14 -179.8(4) . . . . ?
O2 C15 N1 C16 8.1(7) . . . . ?
C13 C14 N1 C15 92.5(5) . . . . ?
C9 C14 N1 C15 -87.8(5) . . . . ?
C13 C14 N1 C16 -95.4(5) . . . . ?
C9 C14 N1 C16 84.2(5) . . . . ?
C17 C16 N1 C15 -94.4(5) . . . . ?
C17 C16 N1 C14 93.6(5) . . . . ?
C25 C24 O1 C7 165.3(5) . . . . ?
C6 C7 O1 C24 -83.1(5) . . . . ?
C8 C7 O1 C24 155.0(4) . . . . ?
C10 C9 S1 C8 -5.7(4) . . . . ?
C14 C9 S1 C8 175.3(3) . . . . ?
C7 C8 S1 C9 -78.7(4) . . . . ?

_refine_diff_density_max         0.231
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.042

