# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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. 
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data_190429_fx023_0m
_database_code_depnum_ccdc_archive 'CCDC 2018743'
loop_
_audit_author_name
_audit_author_address
'Weijun Yao'
;Zhejiang SciTech University
China
;
_audit_update_record             
;
2020-07-24 deposited with the CCDC.	2020-08-24 downloaded from the CCDC.
;
_audit_creation_date             2019-04-30
_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 H24 O4 S2'
_chemical_formula_sum            'C25 H24 O4 S2'
_chemical_formula_weight         452.56
_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'
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   10.917(3)
_cell_length_b                   7.526(3)
_cell_length_c                   28.688(11)
_cell_angle_alpha                90
_cell_angle_beta                 100.154(14)
_cell_angle_gamma                90
_cell_volume                     2320.1(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9848
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      30.06
_cell_measurement_theta_min      2.71
_shelx_estimated_absorpt_T_max   0.960
_shelx_estimated_absorpt_T_min   0.847
_exptl_absorpt_coefficient_mu    0.258
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6769
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0972 before and 0.0465 after correction.
The Ratio of minimum to maximum transmission is 0.9073.
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    1.296
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.664
_exptl_crystal_size_mid          0.305
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            38600
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.548
_diffrn_reflns_theta_min         2.576
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_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                5515
_reflns_number_total             7096
_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         0.454
_refine_diff_density_min         -0.408
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         7096
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0462
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0655P)²+0.7782P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1241
_refine_ls_wR_factor_ref         0.1377
_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:
 C20(H20A,H20B), C22(H22A,H22B), C24(H24A,H24B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C12(H12), C14(H14), C15(H15),
 C16(H16), C17(H17), C18(H18)
2.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C25(H25A,H25B,H25C)
;
_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 0.72018(3) 0.69232(5) 0.52264(2) 0.04145(11) Uani 1 1 d . . . . .
S2 S 0.53918(4) 0.80213(6) 0.58630(2) 0.04662(12) Uani 1 1 d . . . . .
O1 O 0.28830(10) 0.76043(18) 0.44228(4) 0.0503(3) Uani 1 1 d . . . . .
O2 O 0.31665(10) 0.82754(16) 0.51947(4) 0.0465(3) Uani 1 1 d . . . . .
O3 O 0.58840(19) 0.6100(2) 0.70004(6) 0.0866(5) Uani 1 1 d . . . . .
O4 O 0.61577(17) 0.34139(19) 0.67347(5) 0.0735(4) Uani 1 1 d . . . . .
C1 C 0.71746(16) 0.5370(3) 0.38671(6) 0.0528(4) Uani 1 1 d . . . . .
H1 H 0.632216 0.523919 0.376560 0.063 Uiso 1 1 calc R . . . .
C2 C 0.7985(2) 0.4902(3) 0.35664(8) 0.0659(5) Uani 1 1 d . . . . .
H2 H 0.767170 0.448307 0.326383 0.079 Uiso 1 1 calc R . . . .
C3 C 0.92468(19) 0.5053(3) 0.37130(8) 0.0670(5) Uani 1 1 d . . . . .
H3 H 0.978838 0.474291 0.350993 0.080 Uiso 1 1 calc R . . . .
C4 C 0.97072(17) 0.5665(3) 0.41613(8) 0.0621(5) Uani 1 1 d . . . . .
H4 H 1.056227 0.574983 0.426351 0.074 Uiso 1 1 calc R . . . .
C5 C 0.88989(15) 0.6156(3) 0.44616(7) 0.0507(4) Uani 1 1 d . . . . .
H5 H 0.921901 0.657541 0.476343 0.061 Uiso 1 1 calc R . . . .
C6 C 0.76138(13) 0.6030(2) 0.43173(5) 0.0398(3) Uani 1 1 d . . . . .
C7 C 0.67365(13) 0.65856(19) 0.46219(5) 0.0376(3) Uani 1 1 d . . . . .
C8 C 0.54966(13) 0.6921(2) 0.44969(5) 0.0378(3) Uani 1 1 d . . . . .
H8 H 0.507383 0.683715 0.418652 0.045 Uiso 1 1 calc R . . . .
C9 C 0.49042(13) 0.74100(19) 0.48797(5) 0.0352(3) Uani 1 1 d . . . . .
C10 C 0.57181(13) 0.74682(19) 0.53060(5) 0.0361(3) Uani 1 1 d . . . . .
C11 C 0.68584(14) 0.7621(2) 0.62334(5) 0.0410(3) Uani 1 1 d . . . . .
C12 C 0.75893(15) 0.9028(2) 0.63541(5) 0.0441(3) Uani 1 1 d . . . . .
H12 H 0.728724 1.011152 0.622650 0.053 Uiso 1 1 calc R . . . .
C13 C 0.88151(15) 0.9074(2) 0.66646(6) 0.0449(3) Uani 1 1 d . . . . .
C14 C 0.91033(19) 0.8150(3) 0.70875(7) 0.0574(4) Uani 1 1 d . . . . .
H14 H 0.849173 0.748565 0.719559 0.069 Uiso 1 1 calc R . . . .
C15 C 1.0290(2) 0.8208(3) 0.73491(8) 0.0736(6) Uani 1 1 d . . . . .
H15 H 1.047907 0.757380 0.763086 0.088 Uiso 1 1 calc R . . . .
C16 C 1.1195(2) 0.9206(4) 0.71930(9) 0.0790(7) Uani 1 1 d . . . . .
H16 H 1.199807 0.922964 0.736723 0.095 Uiso 1 1 calc R . . . .
C17 C 1.0917(2) 1.0161(4) 0.67842(9) 0.0774(7) Uani 1 1 d . . . . .
H17 H 1.152907 1.084195 0.668151 0.093 Uiso 1 1 calc R . . . .
C18 C 0.97361(19) 1.0116(3) 0.65241(7) 0.0604(5) Uani 1 1 d . . . . .
H18 H 0.954878 1.079263 0.624961 0.072 Uiso 1 1 calc R . . . .
C19 C 0.35637(13) 0.77673(19) 0.48006(5) 0.0371(3) Uani 1 1 d . . . . .
C20 C 0.18394(16) 0.8535(3) 0.51527(7) 0.0553(4) Uani 1 1 d . . . . .
H20A H 0.140118 0.744046 0.505305 0.066 Uiso 1 1 calc R . . . .
H20B H 0.155715 0.944632 0.491936 0.066 Uiso 1 1 calc R . . . .
C21 C 0.1590(2) 0.9083(3) 0.56234(9) 0.0744(6) Uani 1 1 d . . . . .
H21A H 0.071221 0.925849 0.560614 0.112 Uiso 1 1 calc GR . . . .
H21B H 0.202159 1.017262 0.571718 0.112 Uiso 1 1 calc GR . . . .
H21C H 0.187493 0.817440 0.585158 0.112 Uiso 1 1 calc GR . . . .
C22 C 0.71051(14) 0.5730(2) 0.63900(5) 0.0434(3) Uani 1 1 d . . . . .
H22A H 0.797608 0.560551 0.653095 0.052 Uiso 1 1 calc R . . . .
H22B H 0.694305 0.495794 0.611517 0.052 Uiso 1 1 calc R . . . .
C23 C 0.63135(16) 0.5142(2) 0.67436(6) 0.0490(4) Uani 1 1 d . . . . .
C24 C 0.5406(3) 0.2666(4) 0.70636(9) 0.0907(9) Uani 1 1 d . . . . .
H24A H 0.592503 0.246036 0.736983 0.109 Uiso 1 1 calc R . . . .
H24B H 0.475354 0.349344 0.710581 0.109 Uiso 1 1 calc R . . . .
C25 C 0.4871(3) 0.1032(4) 0.68759(11) 0.1063(11) Uani 1 1 d . . . . .
H25A H 0.445533 0.121111 0.655557 0.159 Uiso 1 1 calc GR . . . .
H25B H 0.428170 0.062478 0.706424 0.159 Uiso 1 1 calc GR . . . .
H25C H 0.551460 0.015914 0.688161 0.159 Uiso 1 1 calc GR . . . .


_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 C7 1.7376(16) . ?
S1 C10 1.7246(15) . ?
S2 C10 1.7477(16) . ?
S2 C11 1.7842(16) . ?
O1 C19 1.2074(18) . ?
O2 C19 1.3362(19) . ?
O2 C20 1.4458(19) . ?
O3 C23 1.185(2) . ?
O4 C23 1.311(2) . ?
O4 C24 1.468(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.385(3) . ?
C1 C6 1.388(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.373(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.375(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.387(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.394(2) . ?
C6 C7 1.467(2) . ?
C7 C8 1.362(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.418(2) . ?
C9 C10 1.3800(19) . ?
C9 C19 1.466(2) . ?
C11 C12 1.335(2) . ?
C11 C22 1.502(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.471(2) . ?
C13 C14 1.386(2) . ?
C13 C18 1.390(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.379(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.377(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.363(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.372(3) . ?
C18 H18 0.9300 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21 1.482(3) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 C23 1.510(2) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C24 C25 1.426(4) . ?
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
C10 S1 C7 92.91(7) . . ?
C10 S2 C11 101.42(7) . . ?
C19 O2 C20 115.98(13) . . ?
C23 O4 C24 116.97(18) . . ?
C2 C1 H1 119.4 . . ?
C2 C1 C6 121.11(17) . . ?
C6 C1 H1 119.4 . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.3(2) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.73(18) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.15(18) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 119.5 . . ?
C4 C5 C6 120.95(18) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C5 117.72(15) . . ?
C1 C6 C7 120.12(14) . . ?
C5 C6 C7 122.16(15) . . ?
C6 C7 S1 121.98(11) . . ?
C8 C7 S1 109.75(11) . . ?
C8 C7 C6 128.27(14) . . ?
C7 C8 H8 122.8 . . ?
C7 C8 C9 114.34(13) . . ?
C9 C8 H8 122.8 . . ?
C8 C9 C19 120.48(13) . . ?
C10 C9 C8 112.61(13) . . ?
C10 C9 C19 126.91(13) . . ?
S1 C10 S2 121.69(8) . . ?
C9 C10 S1 110.37(11) . . ?
C9 C10 S2 127.94(11) . . ?
C12 C11 S2 116.95(13) . . ?
C12 C11 C22 127.36(14) . . ?
C22 C11 S2 115.65(11) . . ?
C11 C12 H12 116.1 . . ?
C11 C12 C13 127.88(15) . . ?
C13 C12 H12 116.1 . . ?
C14 C13 C12 124.07(16) . . ?
C14 C13 C18 118.22(17) . . ?
C18 C13 C12 117.72(16) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 C13 120.5(2) . . ?
C15 C14 H14 119.8 . . ?
C14 C15 H15 120.0 . . ?
C16 C15 C14 119.9(2) . . ?
C16 C15 H15 120.0 . . ?
C15 C16 H16 119.9 . . ?
C17 C16 C15 120.3(2) . . ?
C17 C16 H16 119.9 . . ?
C16 C17 H17 120.0 . . ?
C16 C17 C18 120.0(2) . . ?
C18 C17 H17 120.0 . . ?
C13 C18 H18 119.5 . . ?
C17 C18 C13 121.0(2) . . ?
C17 C18 H18 119.5 . . ?
O1 C19 O2 123.26(14) . . ?
O1 C19 C9 124.05(14) . . ?
O2 C19 C9 112.69(12) . . ?
O2 C20 H20A 110.2 . . ?
O2 C20 H20B 110.2 . . ?
O2 C20 C21 107.70(17) . . ?
H20A C20 H20B 108.5 . . ?
C21 C20 H20A 110.2 . . ?
C21 C20 H20B 110.2 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C11 C22 H22A 109.1 . . ?
C11 C22 H22B 109.1 . . ?
C11 C22 C23 112.63(14) . . ?
H22A C22 H22B 107.8 . . ?
C23 C22 H22A 109.1 . . ?
C23 C22 H22B 109.1 . . ?
O3 C23 O4 123.47(18) . . ?
O3 C23 C22 125.12(17) . . ?
O4 C23 C22 111.41(16) . . ?
O4 C24 H24A 109.9 . . ?
O4 C24 H24B 109.9 . . ?
H24A C24 H24B 108.3 . . ?
C25 C24 O4 109.1(2) . . ?
C25 C24 H24A 109.9 . . ?
C25 C24 H24B 109.9 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
