# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_210618-zq01-pwy
_database_code_depnum_ccdc_archive 'CCDC 2090996'
loop_
_audit_author_name
_audit_author_address
'Guangfan Zheng'
;NENU
China
;
_audit_update_record             
;
2021-06-19 deposited with the CCDC.	2022-02-07 downloaded from the CCDC.
;
_audit_creation_date             2021-06-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H28 O3 S'
_chemical_formula_sum            'C28 H28 O3 S'
_chemical_formula_weight         444.56
_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                   14.1193(9)
_cell_length_b                   10.6583(9)
_cell_length_c                   16.1923(13)
_cell_angle_alpha                90
_cell_angle_beta                 95.636(7)
_cell_angle_gamma                90
_cell_volume                     2425.0(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2166
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.6630
_cell_measurement_theta_min      4.7660
_shelx_estimated_absorpt_T_max   0.984
_shelx_estimated_absorpt_T_min   0.976
_exptl_absorpt_coefficient_mu    0.160
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89217
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.38a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.218
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             944
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_unetI/netI     0.0446
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.834
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            10944
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.834
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.556
_diffrn_reflns_theta_min         3.473
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.2375
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.834
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -73.00   9.00   1.00   12.50    --   -9.92 -57.00  60.00   82
  2  ω    -66.00  16.00   1.00   12.50    --   -9.92 -77.00 -30.00   82
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0175142000
_diffrn_orient_matrix_UB_12      0.0161255000
_diffrn_orient_matrix_UB_13      0.0412073000
_diffrn_orient_matrix_UB_21      -0.0471016000
_diffrn_orient_matrix_UB_22      0.0121902000
_diffrn_orient_matrix_UB_23      0.0094923000
_diffrn_orient_matrix_UB_31      -0.0046933000
_diffrn_orient_matrix_UB_32      -0.0633606000
_diffrn_orient_matrix_UB_33      0.0123399000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3307
_reflns_number_total             5671
_reflns_odcompleteness_completeness 99.14
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.453
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         5671
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1045
_refine_ls_R_factor_gt           0.0573
_refine_ls_restrained_S_all      1.026
_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)+(0.0553P)²+0.6431P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1243
_refine_ls_wR_factor_ref         0.1551
_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:
 C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C15(H15), C17(H17), C18(H18), C19(H19), C20(H20),
 C21(H21), C22(H22), C23(H23), C24(H24), C25(H25), C27(H27), C28(H28)
2.c Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C29(H29A,H29B,H29C), C30(H30A,H30B,H30C), C31(H31A,H31B,
 H31C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.95123(4) 0.70364(6) 0.01890(5) 0.0679(2) Uani 1 1 d . . . . .
O1 O 0.52550(11) 0.69470(19) 0.17027(13) 0.0833(6) Uani 1 1 d . . . . .
C2 C 0.71555(14) 0.6970(2) 0.05918(13) 0.0490(5) Uani 1 1 d . . . . .
C3 C 0.92319(14) 0.8426(2) 0.06950(15) 0.0535(6) Uani 1 1 d . . . . .
C4 C 0.63354(14) 0.8948(2) 0.09236(13) 0.0492(5) Uani 1 1 d . . . . .
C5 C 0.76279(14) 0.61727(18) 0.01713(13) 0.0471(5) Uani 1 1 d . . . . .
C6 C 0.61046(15) 0.6831(2) 0.16531(14) 0.0555(6) Uani 1 1 d . . . . .
C7 C 0.65887(14) 0.7607(2) 0.10381(13) 0.0482(5) Uani 1 1 d . . . . .
C8 C 0.86587(14) 0.5896(2) 0.04429(15) 0.0541(5) Uani 1 1 d . . . . .
H8A H 0.8820 0.5102 0.0200 0.065 Uiso 1 1 calc R . . . .
H8B H 0.8725 0.5786 0.1041 0.065 Uiso 1 1 calc R . . . .
O9 O 1.04116(12) 0.6596(2) 0.05698(16) 0.1045(8) Uani 1 1 d . . . . .
O10 O 0.94090(15) 0.72570(19) -0.06904(12) 0.0923(7) Uani 1 1 d . . . . .
C11 C 0.66807(15) 0.5897(2) 0.21622(13) 0.0525(5) Uani 1 1 d . . . . .
C12 C 0.76226(16) 0.6129(2) 0.24361(14) 0.0605(6) Uani 1 1 d . . . . .
H12 H 0.7913 0.6864 0.2282 0.073 Uiso 1 1 calc R . . . .
C13 C 0.63741(17) 0.9538(2) 0.01667(16) 0.0639(6) Uani 1 1 d . . . . .
H13 H 0.6563 0.9089 -0.0281 0.077 Uiso 1 1 calc R . . . .
C14 C 0.88326(17) 1.0642(3) 0.1482(2) 0.0710(7) Uani 1 1 d . . . . .
C15 C 0.60530(16) 0.9648(2) 0.15774(15) 0.0622(6) Uani 1 1 d . . . . .
H15 H 0.6019 0.9269 0.2091 0.075 Uiso 1 1 calc R . . . .
C16 C 0.71209(16) 0.5408(2) -0.05449(15) 0.0596(6) Uani 1 1 d . . . . .
C17 C 0.94064(17) 0.8522(3) 0.15470(17) 0.0692(7) Uani 1 1 d . . . . .
H17 H 0.9662 0.7848 0.1858 0.083 Uiso 1 1 calc R . . . .
C18 C 0.88564(18) 0.9421(2) 0.02432(16) 0.0675(7) Uani 1 1 d . . . . .
H18 H 0.8729 0.9357 -0.0330 0.081 Uiso 1 1 calc R . . . .
C19 C 0.62671(19) 0.4790(2) 0.24013(15) 0.0670(7) Uani 1 1 d . . . . .
H19 H 0.5631 0.4631 0.2229 0.080 Uiso 1 1 calc R . . . .
C20 C 0.7714(2) 0.4170(3) 0.31573(16) 0.0805(8) Uani 1 1 d . . . . .
H20 H 0.8064 0.3588 0.3489 0.097 Uiso 1 1 calc R . . . .
C21 C 0.6133(2) 1.0798(3) 0.0071(2) 0.0805(8) Uani 1 1 d . . . . .
H21 H 0.6157 1.1186 -0.0441 0.097 Uiso 1 1 calc R . . . .
C22 C 0.91971(19) 0.9631(3) 0.19315(18) 0.0785(8) Uani 1 1 d . . . . .
H22 H 0.9305 0.9693 0.2506 0.094 Uiso 1 1 calc R . . . .
C23 C 0.6784(2) 0.3928(3) 0.28881(17) 0.0791(8) Uani 1 1 d . . . . .
H23 H 0.6503 0.3182 0.3034 0.095 Uiso 1 1 calc R . . . .
C24 C 0.86673(19) 1.0524(2) 0.06447(19) 0.0765(8) Uani 1 1 d . . . . .
H24 H 0.8420 1.1203 0.0334 0.092 Uiso 1 1 calc R . . . .
C25 C 0.58611(19) 1.1470(3) 0.0729(2) 0.0844(9) Uani 1 1 d . . . . .
H25 H 0.5703 1.2314 0.0664 0.101 Uiso 1 1 calc R . . . .
C26 C 0.7666(2) 0.5471(3) -0.13104(16) 0.0883(9) Uani 1 1 d . . . . .
H26A H 0.7681 0.6322 -0.1502 0.132 Uiso 1 1 calc GR . . . .
H26B H 0.7356 0.4952 -0.1740 0.132 Uiso 1 1 calc GR . . . .
H26C H 0.8305 0.5179 -0.1172 0.132 Uiso 1 1 calc GR . . . .
C27 C 0.8135(2) 0.5266(3) 0.29408(16) 0.0774(8) Uani 1 1 d . . . . .
H27 H 0.8765 0.5430 0.3133 0.093 Uiso 1 1 calc R . . . .
C28 C 0.58213(19) 1.0901(3) 0.1478(2) 0.0777(8) Uani 1 1 d . . . . .
H28 H 0.5637 1.1359 0.1924 0.093 Uiso 1 1 calc R . . . .
C29 C 0.6113(2) 0.5888(3) -0.0763(2) 0.1085(12) Uani 1 1 d . . . . .
H29A H 0.5767 0.5843 -0.0282 0.163 Uiso 1 1 calc GR . . . .
H29B H 0.5800 0.5382 -0.1198 0.163 Uiso 1 1 calc GR . . . .
H29C H 0.6135 0.6743 -0.0946 0.163 Uiso 1 1 calc GR . . . .
C30 C 0.8610(2) 1.1860(3) 0.1901(2) 0.1120(13) Uani 1 1 d . . . . .
H30A H 0.8753 1.1776 0.2490 0.168 Uiso 1 1 calc GR . . . .
H30B H 0.7948 1.2055 0.1777 0.168 Uiso 1 1 calc GR . . . .
H30C H 0.8988 1.2522 0.1702 0.168 Uiso 1 1 calc GR . . . .
C31 C 0.7095(3) 0.4039(3) -0.0257(2) 0.0998(10) Uani 1 1 d . . . . .
H31A H 0.7732 0.3717 -0.0175 0.150 Uiso 1 1 calc GR . . . .
H31B H 0.6730 0.3549 -0.0672 0.150 Uiso 1 1 calc GR . . . .
H31C H 0.6807 0.3996 0.0255 0.150 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 C3 1.757(2) . ?
S1 C8 1.788(2) . ?
S1 O9 1.435(2) . ?
S1 O10 1.436(2) . ?
O1 C6 1.216(2) . ?
C2 C5 1.311(3) . ?
C2 C7 1.318(3) . ?
C3 C17 1.381(3) . ?
C3 C18 1.366(3) . ?
C4 C7 1.481(3) . ?
C4 C13 1.383(3) . ?
C4 C15 1.385(3) . ?
C5 C8 1.508(3) . ?
C5 C16 1.535(3) . ?
C6 C7 1.509(3) . ?
C6 C11 1.484(3) . ?
C11 C12 1.382(3) . ?
C11 C19 1.388(3) . ?
C12 C27 1.386(4) . ?
C13 C21 1.390(3) . ?
C14 C22 1.372(4) . ?
C14 C24 1.359(4) . ?
C14 C30 1.512(4) . ?
C15 C28 1.380(4) . ?
C16 C26 1.523(4) . ?
C16 C29 1.521(3) . ?
C16 C31 1.533(4) . ?
C17 C22 1.381(4) . ?
C18 C24 1.382(4) . ?
C19 C23 1.374(4) . ?
C20 C23 1.367(4) . ?
C20 C27 1.371(4) . ?
C21 C25 1.369(4) . ?
C25 C28 1.362(4) . ?

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
C3 S1 C8 106.15(10) . . ?
O9 S1 C3 107.80(12) . . ?
O9 S1 C8 105.48(13) . . ?
O9 S1 O10 118.61(14) . . ?
O10 S1 C3 108.59(12) . . ?
O10 S1 C8 109.52(11) . . ?
C5 C2 C7 170.3(2) . . ?
C17 C3 S1 120.1(2) . . ?
C18 C3 S1 119.90(19) . . ?
C18 C3 C17 119.9(2) . . ?
C13 C4 C7 121.31(19) . . ?
C13 C4 C15 118.1(2) . . ?
C15 C4 C7 120.5(2) . . ?
C2 C5 C8 120.07(19) . . ?
C2 C5 C16 120.85(19) . . ?
C8 C5 C16 118.78(18) . . ?
O1 C6 C7 120.1(2) . . ?
O1 C6 C11 121.5(2) . . ?
C11 C6 C7 118.39(18) . . ?
C2 C7 C4 125.50(19) . . ?
C2 C7 C6 114.7(2) . . ?
C4 C7 C6 119.49(18) . . ?
C5 C8 S1 116.93(15) . . ?
C12 C11 C6 121.0(2) . . ?
C12 C11 C19 118.7(2) . . ?
C19 C11 C6 120.2(2) . . ?
C11 C12 C27 120.0(2) . . ?
C4 C13 C21 120.5(2) . . ?
C22 C14 C30 121.3(3) . . ?
C24 C14 C22 118.4(2) . . ?
C24 C14 C30 120.3(3) . . ?
C28 C15 C4 121.0(2) . . ?
C26 C16 C5 110.9(2) . . ?
C26 C16 C31 108.5(2) . . ?
C29 C16 C5 110.7(2) . . ?
C29 C16 C26 109.4(2) . . ?
C29 C16 C31 109.9(2) . . ?
C31 C16 C5 107.4(2) . . ?
C22 C17 C3 119.3(3) . . ?
C3 C18 C24 119.4(2) . . ?
C23 C19 C11 120.9(2) . . ?
C23 C20 C27 120.4(3) . . ?
C25 C21 C13 120.2(3) . . ?
C14 C22 C17 121.2(3) . . ?
C20 C23 C19 119.8(3) . . ?
C14 C24 C18 121.8(3) . . ?
C28 C25 C21 119.9(3) . . ?
C20 C27 C12 120.1(3) . . ?
C25 C28 C15 120.3(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.180
_oxdiff_exptl_absorpt_empirical_full_min 0.880
