# Electronic Supplementary Material (ESI) for ChemComm.
# 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_230215d
_database_code_depnum_ccdc_archive 'CCDC 2242756'
loop_
_audit_author_name
_audit_author_address
'Wenwen Cui'
;Qingdao University of Science and Technology
China
;
_audit_update_record             
;
2023-02-17 deposited with the CCDC.	2023-04-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H24 O S'
_chemical_formula_weight         312.45

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'

_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                   20.6821(17)
_cell_length_b                   14.2922(12)
_cell_length_c                   5.8697(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.440(2)
_cell_angle_gamma                90.00
_cell_volume                     1733.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    820
_cell_measurement_theta_min      2.397
_cell_measurement_theta_max      26.752

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             672
_exptl_absorpt_coefficient_mu    0.187
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9375
_exptl_absorpt_correction_T_max  0.9926
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8197
_diffrn_reflns_av_R_equivalents  0.1345
_diffrn_reflns_av_sigmaI/netI    0.1483
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         2.43
_diffrn_reflns_theta_max         25.02
_reflns_number_total             3025
_reflns_number_gt                1249
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0168P)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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3025
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2016
_refine_ls_R_factor_gt           0.0792
_refine_ls_wR_factor_ref         0.1424
_refine_ls_wR_factor_gt          0.1191
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_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
O1 O 0.78690(15) 0.4084(3) 1.0550(6) 0.0927(12) Uani 1 1 d . . .
S1 S 0.42328(6) 0.42014(11) 0.7363(2) 0.0934(5) Uani 1 1 d . . .
C1 C 0.8570(2) 0.3814(3) 0.7832(7) 0.0534(11) Uani 1 1 d . . .
C2 C 0.9116(2) 0.4098(3) 0.9123(6) 0.0623(13) Uani 1 1 d . . .
H2 H 0.9067 0.4337 1.0580 0.075 Uiso 1 1 calc R . .
C3 C 0.9725(2) 0.4033(3) 0.8289(8) 0.0708(14) Uani 1 1 d . . .
H3 H 1.0075 0.4249 0.9185 0.085 Uiso 1 1 calc R . .
C4 C 0.9835(2) 0.3663(3) 0.6194(9) 0.0660(13) Uani 1 1 d . . .
C5 C 0.9295(2) 0.3389(3) 0.4915(7) 0.0641(13) Uani 1 1 d . . .
H5 H 0.9349 0.3147 0.3465 0.077 Uiso 1 1 calc R . .
C6 C 0.8688(2) 0.3457(3) 0.5687(7) 0.0638(13) Uani 1 1 d . . .
H6 H 0.8340 0.3259 0.4753 0.077 Uiso 1 1 calc R . .
C7 C 0.7919(2) 0.3858(3) 0.8863(7) 0.0478(12) Uani 1 1 d . . .
C8 C 0.73432(18) 0.3545(3) 0.7332(6) 0.0637(13) Uani 1 1 d . . .
H8A H 0.7379 0.3822 0.5835 0.076 Uiso 1 1 calc R . .
H8B H 0.7358 0.2870 0.7156 0.076 Uiso 1 1 calc R . .
C9 C 0.67083(19) 0.3813(3) 0.8254(7) 0.0659(13) Uani 1 1 d . . .
H9A H 0.6705 0.4485 0.8482 0.079 Uiso 1 1 calc R . .
H9B H 0.6673 0.3521 0.9736 0.079 Uiso 1 1 calc R . .
C10 C 0.61154(19) 0.3548(3) 0.6775(7) 0.0685(13) Uani 1 1 d . . .
H10A H 0.6167 0.3789 0.5249 0.082 Uiso 1 1 calc R . .
H10B H 0.6093 0.2871 0.6670 0.082 Uiso 1 1 calc R . .
C11 C 0.54972(18) 0.3900(3) 0.7622(6) 0.0695(13) Uani 1 1 d . . .
H11A H 0.5534 0.4571 0.7836 0.083 Uiso 1 1 calc R . .
H11B H 0.5432 0.3623 0.9102 0.083 Uiso 1 1 calc R . .
C12 C 0.49123(17) 0.3706(3) 0.6105(6) 0.0694(14) Uani 1 1 d . . .
H12A H 0.4853 0.3036 0.5927 0.083 Uiso 1 1 calc R . .
H12B H 0.4966 0.3977 0.4611 0.083 Uiso 1 1 calc R . .
C13 C 0.35865(18) 0.3975(3) 0.5395(7) 0.0532(11) Uani 1 1 d . . .
C14 C 0.2994(2) 0.4265(3) 0.6024(6) 0.0558(12) Uani 1 1 d . . .
H14 H 0.2956 0.4563 0.7421 0.067 Uiso 1 1 calc R . .
C15 C 0.24473(18) 0.4127(3) 0.4633(7) 0.0596(12) Uani 1 1 d . . .
H15 H 0.2050 0.4346 0.5095 0.072 Uiso 1 1 calc R . .
C16 C 0.2479(2) 0.3667(3) 0.2567(7) 0.0513(11) Uani 1 1 d . . .
C17 C 0.3072(2) 0.3389(3) 0.1951(7) 0.0576(12) Uani 1 1 d . . .
H17 H 0.3110 0.3098 0.0546 0.069 Uiso 1 1 calc R . .
C18 C 0.3623(2) 0.3520(3) 0.3330(7) 0.0597(12) Uani 1 1 d . . .
H18 H 0.4020 0.3300 0.2865 0.072 Uiso 1 1 calc R . .
C19 C 1.0498(2) 0.3605(3) 0.5362(8) 0.0982(17) Uani 1 1 d . . .
H19A H 1.0520 0.3103 0.4280 0.147 Uiso 1 1 calc R . .
H19B H 1.0798 0.3488 0.6623 0.147 Uiso 1 1 calc R . .
H19C H 1.0606 0.4184 0.4642 0.147 Uiso 1 1 calc R . .
C20 C 0.18849(18) 0.3503(3) 0.1045(6) 0.0735(14) Uani 1 1 d . . .
H20A H 0.1989 0.3084 -0.0165 0.110 Uiso 1 1 calc R . .
H20B H 0.1737 0.4088 0.0410 0.110 Uiso 1 1 calc R . .
H20C H 0.1551 0.3232 0.1920 0.110 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
O1 C7 1.051(4) . ?
S1 C13 1.759(4) . ?
S1 C12 1.763(4) . ?
C1 C6 1.389(5) . ?
C1 C2 1.393(5) . ?
C1 C7 1.501(5) . ?
C2 C3 1.373(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.367(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.376(5) . ?
C4 C19 1.476(5) . ?
C5 C6 1.357(5) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.528(5) . ?
C8 C9 1.491(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.520(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.480(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.497(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.359(4) . ?
C13 C18 1.381(5) . ?
C14 C15 1.380(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.383(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.353(5) . ?
C16 C20 1.506(5) . ?
C17 C18 1.383(4) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 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
C13 S1 C12 104.4(2) . . ?
C6 C1 C2 115.6(4) . . ?
C6 C1 C7 125.1(4) . . ?
C2 C1 C7 119.3(4) . . ?
C3 C2 C1 121.3(4) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
C4 C3 C2 122.6(4) . . ?
C4 C3 H3 118.7 . . ?
C2 C3 H3 118.7 . . ?
C3 C4 C5 116.0(4) . . ?
C3 C4 C19 120.9(5) . . ?
C5 C4 C19 123.1(5) . . ?
C6 C5 C4 122.6(4) . . ?
C6 C5 H5 118.7 . . ?
C4 C5 H5 118.7 . . ?
C5 C6 C1 121.9(4) . . ?
C5 C6 H6 119.0 . . ?
C1 C6 H6 119.0 . . ?
O1 C7 C1 121.3(4) . . ?
O1 C7 C8 122.5(5) . . ?
C1 C7 C8 116.2(4) . . ?
C9 C8 C7 112.8(3) . . ?
C9 C8 H8A 109.0 . . ?
C7 C8 H8A 109.0 . . ?
C9 C8 H8B 109.0 . . ?
C7 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
C8 C9 C10 115.5(3) . . ?
C8 C9 H9A 108.4 . . ?
C10 C9 H9A 108.4 . . ?
C8 C9 H9B 108.4 . . ?
C10 C9 H9B 108.4 . . ?
H9A C9 H9B 107.5 . . ?
C11 C10 C9 114.3(3) . . ?
C11 C10 H10A 108.7 . . ?
C9 C10 H10A 108.7 . . ?
C11 C10 H10B 108.7 . . ?
C9 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
C10 C11 C12 115.2(3) . . ?
C10 C11 H11A 108.5 . . ?
C12 C11 H11A 108.5 . . ?
C10 C11 H11B 108.5 . . ?
C12 C11 H11B 108.5 . . ?
H11A C11 H11B 107.5 . . ?
C11 C12 S1 108.4(3) . . ?
C11 C12 H12A 110.0 . . ?
S1 C12 H12A 110.0 . . ?
C11 C12 H12B 110.0 . . ?
S1 C12 H12B 110.0 . . ?
H12A C12 H12B 108.4 . . ?
C14 C13 C18 117.8(4) . . ?
C14 C13 S1 115.7(3) . . ?
C18 C13 S1 126.5(3) . . ?
C13 C14 C15 121.4(4) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 H14 119.3 . . ?
C14 C15 C16 121.2(4) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C17 C16 C15 116.8(4) . . ?
C17 C16 C20 121.4(4) . . ?
C15 C16 C20 121.7(4) . . ?
C16 C17 C18 122.6(4) . . ?
C16 C17 H17 118.7 . . ?
C18 C17 H17 118.7 . . ?
C13 C18 C17 120.2(4) . . ?
C13 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C4 C19 H19A 109.5 . . ?
C4 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C4 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C16 C20 H20A 109.5 . . ?
C16 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C16 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

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 0.7(6) . . . . ?
C7 C1 C2 C3 177.1(4) . . . . ?
C1 C2 C3 C4 -2.1(7) . . . . ?
C2 C3 C4 C5 2.4(7) . . . . ?
C2 C3 C4 C19 -179.9(4) . . . . ?
C3 C4 C5 C6 -1.5(7) . . . . ?
C19 C4 C5 C6 -179.1(4) . . . . ?
C4 C5 C6 C1 0.2(7) . . . . ?
C2 C1 C6 C5 0.2(6) . . . . ?
C7 C1 C6 C5 -176.0(4) . . . . ?
C6 C1 C7 O1 174.8(5) . . . . ?
C2 C1 C7 O1 -1.3(7) . . . . ?
C6 C1 C7 C8 -4.6(6) . . . . ?
C2 C1 C7 C8 179.3(4) . . . . ?
O1 C7 C8 C9 14.0(7) . . . . ?
C1 C7 C8 C9 -166.6(3) . . . . ?
C7 C8 C9 C10 178.2(3) . . . . ?
C8 C9 C10 C11 -174.5(4) . . . . ?
C9 C10 C11 C12 175.8(3) . . . . ?
C10 C11 C12 S1 -178.6(3) . . . . ?
C13 S1 C12 C11 177.6(3) . . . . ?
C12 S1 C13 C14 177.7(3) . . . . ?
C12 S1 C13 C18 -0.7(4) . . . . ?
C18 C13 C14 C15 -1.2(6) . . . . ?
S1 C13 C14 C15 -179.8(3) . . . . ?
C13 C14 C15 C16 1.5(6) . . . . ?
C14 C15 C16 C17 -2.0(6) . . . . ?
C14 C15 C16 C20 179.4(3) . . . . ?
C15 C16 C17 C18 2.3(6) . . . . ?
C20 C16 C17 C18 -179.1(3) . . . . ?
C14 C13 C18 C17 1.4(6) . . . . ?
S1 C13 C18 C17 179.8(3) . . . . ?
C16 C17 C18 C13 -2.0(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.043
