# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_200426_xjw426157_1_0m
_database_code_depnum_ccdc_archive 'CCDC 2016595'
loop_
_audit_author_name
_audit_author_address
'xie jianwei'
;department of chemistry of zhejiang university
China
;
_audit_update_record             
;
2020-07-15 deposited with the CCDC.	2021-06-29 downloaded from the CCDC.
;
_audit_creation_date             2020-04-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H23 N O3 S2'
_chemical_formula_sum            'C25 H23 N O3 S2'
_chemical_formula_weight         449.56
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.009(2)
_cell_length_b                   9.253(3)
_cell_length_c                   13.987(4)
_cell_angle_alpha                106.407(11)
_cell_angle_beta                 94.581(11)
_cell_angle_gamma                91.510(13)
_cell_volume                     1113.5(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9892
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      27.12
_cell_measurement_theta_min      2.30
_shelx_estimated_absorpt_T_max   0.949
_shelx_estimated_absorpt_T_min   0.903
_exptl_absorpt_coefficient_mu    0.266
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1085 before and 0.0370 after correction.
The Ratio of minimum to maximum transmission is 0.9347.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            18102
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.093
_diffrn_reflns_theta_min         2.271
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4663
_reflns_number_total             4900
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.313
_refine_diff_density_min         -0.398
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         4900
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0324
_refine_ls_R_factor_gt           0.0310
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0388P)²+0.4422P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0816
_refine_ls_wR_factor_ref         0.0827
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C23(H23A,H23B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C11(H11), C12(H12), C14(H14), C15(H15),
 C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C24(H24)
2.c X=CH2 refined with riding coordinates:
 C25(H25A,H25B)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
S1 S 0.71617(3) 0.73264(3) 0.29511(2) 0.02544(9) Uani 1 1 d . . . . .
S2 S 0.49900(3) 0.26962(3) 0.32945(2) 0.02144(8) Uani 1 1 d . . . . .
O1 O 0.72090(13) 0.85863(10) 0.38310(8) 0.0386(3) Uani 1 1 d . . . . .
O2 O 0.83311(11) 0.71990(12) 0.23038(8) 0.0369(2) Uani 1 1 d . . . . .
O3 O 0.70504(10) 0.41974(10) 0.18090(6) 0.02573(19) Uani 1 1 d . . . . .
N1 N 0.71303(11) 0.57983(11) 0.33858(7) 0.0204(2) Uani 1 1 d . . . . .
C1 C 0.83752(13) 0.52086(14) 0.58066(9) 0.0227(2) Uani 1 1 d . . . . .
H1 H 0.837078 0.621339 0.622757 0.027 Uiso 1 1 calc R . . . .
C2 C 0.90414(14) 0.41060(15) 0.61669(9) 0.0256(3) Uani 1 1 d . . . . .
H2 H 0.949380 0.435548 0.683390 0.031 Uiso 1 1 calc R . . . .
C3 C 0.90443(14) 0.26406(15) 0.55506(10) 0.0265(3) Uani 1 1 d . . . . .
H3 H 0.949112 0.188506 0.579992 0.032 Uiso 1 1 calc R . . . .
C4 C 0.83975(13) 0.22685(13) 0.45695(9) 0.0227(2) Uani 1 1 d . . . . .
H4 H 0.840450 0.126179 0.415188 0.027 Uiso 1 1 calc R . . . .
C5 C 0.77372(12) 0.33740(12) 0.41972(8) 0.0176(2) Uani 1 1 d . . . . .
C6 C 0.77131(13) 0.48410(13) 0.48274(8) 0.0190(2) Uani 1 1 d . . . . .
C7 C 0.69239(15) 0.60158(13) 0.44559(9) 0.0239(2) Uani 1 1 d . . . . .
H7A H 0.584710 0.594219 0.454213 0.029 Uiso 1 1 calc R . . . .
H7B H 0.732523 0.703319 0.485300 0.029 Uiso 1 1 calc R . . . .
C8 C 0.70686(12) 0.43705(13) 0.27050(8) 0.0185(2) Uani 1 1 d . . . . .
C9 C 0.70018(12) 0.30216(12) 0.31366(8) 0.0172(2) Uani 1 1 d . . . . .
C10 C 0.54294(13) 0.72367(13) 0.22585(9) 0.0217(2) Uani 1 1 d . . . . .
C11 C 0.53490(14) 0.67610(13) 0.12199(9) 0.0233(2) Uani 1 1 d . . . . .
H11 H 0.621908 0.647539 0.088573 0.028 Uiso 1 1 calc R . . . .
C12 C 0.39782(14) 0.67085(13) 0.06765(9) 0.0252(3) Uani 1 1 d . . . . .
H12 H 0.391750 0.640158 -0.003401 0.030 Uiso 1 1 calc R . . . .
C13 C 0.26921(14) 0.71001(13) 0.11600(10) 0.0253(3) Uani 1 1 d . . . . .
C14 C 0.28031(15) 0.75766(14) 0.22061(10) 0.0280(3) Uani 1 1 d . . . . .
H14 H 0.193154 0.784863 0.254147 0.034 Uiso 1 1 calc R . . . .
C15 C 0.41641(15) 0.76590(14) 0.27626(9) 0.0269(3) Uani 1 1 d . . . . .
H15 H 0.423306 0.799634 0.347292 0.032 Uiso 1 1 calc R . . . .
C16 C 0.12032(16) 0.70298(17) 0.05667(12) 0.0366(3) Uani 1 1 d . . . . .
H16A H 0.096849 0.804411 0.053451 0.055 Uiso 1 1 calc GR . . . .
H16B H 0.042800 0.663582 0.089288 0.055 Uiso 1 1 calc GR . . . .
H16C H 0.124683 0.636394 -0.011259 0.055 Uiso 1 1 calc GR . . . .
C17 C 0.40710(12) 0.22807(13) 0.20669(8) 0.0193(2) Uani 1 1 d . . . . .
C18 C 0.40325(13) 0.08156(13) 0.14200(9) 0.0214(2) Uani 1 1 d . . . . .
H18 H 0.455244 0.005379 0.162001 0.026 Uiso 1 1 calc R . . . .
C19 C 0.32347(14) 0.04740(14) 0.04858(9) 0.0252(2) Uani 1 1 d . . . . .
H19 H 0.323187 -0.051507 0.004117 0.030 Uiso 1 1 calc R . . . .
C20 C 0.24401(14) 0.15739(15) 0.01987(10) 0.0284(3) Uani 1 1 d . . . . .
H20 H 0.188327 0.133466 -0.043672 0.034 Uiso 1 1 calc R . . . .
C21 C 0.24642(14) 0.30250(15) 0.08457(10) 0.0292(3) Uani 1 1 d . . . . .
H21 H 0.191452 0.377466 0.065217 0.035 Uiso 1 1 calc R . . . .
C22 C 0.32851(13) 0.33887(14) 0.17730(10) 0.0246(2) Uani 1 1 d . . . . .
H22 H 0.331194 0.438803 0.220596 0.030 Uiso 1 1 calc R . . . .
C23 C 0.75676(13) 0.16314(13) 0.23883(8) 0.0198(2) Uani 1 1 d . . . . .
H23A H 0.739616 0.073813 0.262959 0.024 Uiso 1 1 calc R . . . .
H23B H 0.697263 0.145466 0.173575 0.024 Uiso 1 1 calc R . . . .
C24 C 0.91910(14) 0.17688(14) 0.22323(9) 0.0246(2) Uani 1 1 d . . . . .
H24 H 0.953593 0.263076 0.205693 0.030 Uiso 1 1 calc R . . . .
C25 C 1.01632(15) 0.07701(16) 0.23235(12) 0.0355(3) Uani 1 1 d . . . . .
H25A H 0.985314 -0.010404 0.249815 0.043 Uiso 1 1 calc R . . . .
H25B H 1.117562 0.092261 0.221483 0.043 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 O1 1.4332(11) . ?
S1 O2 1.4291(11) . ?
S1 N1 1.6900(10) . ?
S1 C10 1.7570(13) . ?
S2 C9 1.8701(12) . ?
S2 C17 1.7791(12) . ?
O3 C8 1.2166(14) . ?
N1 C7 1.4805(15) . ?
N1 C8 1.3901(15) . ?
C1 H1 0.9500 . ?
C1 C2 1.3891(18) . ?
C1 C6 1.3938(16) . ?
C2 H2 0.9500 . ?
C2 C3 1.3864(19) . ?
C3 H3 0.9500 . ?
C3 C4 1.3915(17) . ?
C4 H4 0.9500 . ?
C4 C5 1.3981(16) . ?
C5 C6 1.3960(16) . ?
C5 C9 1.5181(15) . ?
C6 C7 1.5027(16) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.5340(15) . ?
C9 C23 1.5392(15) . ?
C10 C11 1.3891(17) . ?
C10 C15 1.3947(18) . ?
C11 H11 0.9500 . ?
C11 C12 1.3897(18) . ?
C12 H12 0.9500 . ?
C12 C13 1.3928(18) . ?
C13 C14 1.3983(19) . ?
C13 C16 1.5097(18) . ?
C14 H14 0.9500 . ?
C14 C15 1.3871(19) . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.3991(16) . ?
C17 C22 1.3969(17) . ?
C18 H18 0.9500 . ?
C18 C19 1.3888(17) . ?
C19 H19 0.9500 . ?
C19 C20 1.3902(19) . ?
C20 H20 0.9500 . ?
C20 C21 1.3897(19) . ?
C21 H21 0.9500 . ?
C21 C22 1.3890(18) . ?
C22 H22 0.9500 . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.5032(16) . ?
C24 H24 0.9500 . ?
C24 C25 1.3149(19) . ?
C25 H25A 0.9500 . ?
C25 H25B 0.9500 . ?

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
O1 S1 N1 104.51(6) . . ?
O1 S1 C10 108.59(6) . . ?
O2 S1 O1 119.24(7) . . ?
O2 S1 N1 108.57(6) . . ?
O2 S1 C10 109.66(6) . . ?
N1 S1 C10 105.32(5) . . ?
C17 S2 C9 104.91(5) . . ?
C7 N1 S1 118.65(8) . . ?
C8 N1 S1 118.89(8) . . ?
C8 N1 C7 121.71(9) . . ?
C2 C1 H1 120.0 . . ?
C2 C1 C6 120.01(11) . . ?
C6 C1 H1 120.0 . . ?
C1 C2 H2 120.1 . . ?
C3 C2 C1 119.83(11) . . ?
C3 C2 H2 120.1 . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.47(11) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.10(11) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C9 122.12(10) . . ?
C6 C5 C4 119.14(10) . . ?
C6 C5 C9 118.72(10) . . ?
C1 C6 C5 120.43(10) . . ?
C1 C6 C7 119.93(10) . . ?
C5 C6 C7 119.62(10) . . ?
N1 C7 C6 110.27(9) . . ?
N1 C7 H7A 109.6 . . ?
N1 C7 H7B 109.6 . . ?
C6 C7 H7A 109.6 . . ?
C6 C7 H7B 109.6 . . ?
H7A C7 H7B 108.1 . . ?
O3 C8 N1 121.66(10) . . ?
O3 C8 C9 121.54(10) . . ?
N1 C8 C9 116.80(9) . . ?
C5 C9 S2 103.06(7) . . ?
C5 C9 C8 113.10(9) . . ?
C5 C9 C23 114.96(9) . . ?
C8 C9 S2 105.69(7) . . ?
C8 C9 C23 109.25(9) . . ?
C23 C9 S2 110.21(8) . . ?
C11 C10 S1 119.38(10) . . ?
C11 C10 C15 121.29(11) . . ?
C15 C10 S1 119.33(10) . . ?
C10 C11 H11 120.5 . . ?
C10 C11 C12 119.09(11) . . ?
C12 C11 H11 120.5 . . ?
C11 C12 H12 119.6 . . ?
C11 C12 C13 120.87(12) . . ?
C13 C12 H12 119.6 . . ?
C12 C13 C14 118.92(12) . . ?
C12 C13 C16 120.68(12) . . ?
C14 C13 C16 120.39(12) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 C13 121.13(12) . . ?
C15 C14 H14 119.4 . . ?
C10 C15 H15 120.7 . . ?
C14 C15 C10 118.69(12) . . ?
C14 C15 H15 120.7 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 S2 120.23(9) . . ?
C22 C17 S2 119.97(9) . . ?
C22 C17 C18 119.60(11) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 120.05(11) . . ?
C19 C18 H18 120.0 . . ?
C18 C19 H19 119.9 . . ?
C18 C19 C20 120.26(11) . . ?
C20 C19 H19 119.9 . . ?
C19 C20 H20 120.2 . . ?
C21 C20 C19 119.69(12) . . ?
C21 C20 H20 120.2 . . ?
C20 C21 H21 119.7 . . ?
C22 C21 C20 120.57(12) . . ?
C22 C21 H21 119.7 . . ?
C17 C22 H22 120.1 . . ?
C21 C22 C17 119.80(11) . . ?
C21 C22 H22 120.1 . . ?
C9 C23 H23A 108.7 . . ?
C9 C23 H23B 108.7 . . ?
H23A C23 H23B 107.6 . . ?
C24 C23 C9 114.17(9) . . ?
C24 C23 H23A 108.7 . . ?
C24 C23 H23B 108.7 . . ?
C23 C24 H24 118.0 . . ?
C25 C24 C23 124.06(12) . . ?
C25 C24 H24 118.0 . . ?
C24 C25 H25A 120.0 . . ?
C24 C25 H25B 120.0 . . ?
H25A C25 H25B 120.0 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
