# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_cxy1040_0m
_database_code_depnum_ccdc_archive 'CCDC 2106134'
loop_
_audit_author_name
_audit_author_address
'XIAOFENG RAO'
;Southern University of Science and Technology
China
;
_audit_update_record             
;
2021-08-28 deposited with the CCDC.	2022-05-09 downloaded from the CCDC.
;
_audit_creation_date             2019-12-09
_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         'C18 H20 O2 S'
_chemical_formula_sum            'C18 H20 O2 S'
_chemical_formula_weight         300.40
_chemical_absolute_configuration ad
_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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.0924(4)
_cell_length_b                   8.7294(4)
_cell_length_c                   10.8209(4)
_cell_angle_alpha                90
_cell_angle_beta                 110.7260(10)
_cell_angle_gamma                90
_cell_volume                     803.28(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9916
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.55
_cell_measurement_theta_min      2.39
_shelx_estimated_absorpt_T_max   0.945
_shelx_estimated_absorpt_T_min   0.930
_exptl_absorpt_coefficient_mu    0.203
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6886
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0995 before and 0.0507 after correction. The Ratio of minimum to maximum transmission is 0.9229. 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    1.242
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.28
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            21390
_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         30.597
_diffrn_reflns_theta_min         2.395
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker PHOTON 100 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'BrukerD8 venture microsource'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.885
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                4686
_reflns_number_total             4947
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.710
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 
;
 Flack x determined using 2099 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         4947
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0326
_refine_ls_restrained_S_all      1.053
_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)+(0.0448P)²+0.1624P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0822
_refine_ls_wR_factor_ref         0.0842
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12),
 C17(H17), C18(H18)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), 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 0.33826(5) 0.42512(5) 0.50144(4) 0.02016(11) Uani 1 1 d . . . . .
O1 O 0.43906(15) 0.43404(16) 0.25171(13) 0.0212(3) Uani 1 1 d . . . . .
O2 O 0.28666(17) 0.22161(16) 0.20303(14) 0.0238(3) Uani 1 1 d . . . . .
C1 C 0.7472(2) 0.2716(2) 0.0753(2) 0.0234(4) Uani 1 1 d . . . . .
H1 H 0.817717 0.235549 0.034706 0.028 Uiso 1 1 calc R . . . .
C2 C 0.7497(2) 0.2084(2) 0.1933(2) 0.0243(4) Uani 1 1 d . . . . .
H2 H 0.823080 0.129804 0.233978 0.029 Uiso 1 1 calc R . . . .
C3 C 0.6453(2) 0.2591(2) 0.2533(2) 0.0213(4) Uani 1 1 d . . . . .
H3 H 0.646797 0.216208 0.334468 0.026 Uiso 1 1 calc R . . . .
C4 C 0.5402(2) 0.3729(2) 0.19138(18) 0.0173(3) Uani 1 1 d . . . . .
C5 C 0.3159(2) 0.3463(2) 0.25268(17) 0.0167(3) Uani 1 1 d . . . . .
C6 C 0.22151(18) 0.4269(2) 0.32417(15) 0.0154(3) Uani 1 1 d . . . . .
H6 H 0.124677 0.364748 0.310683 0.019 Uiso 1 1 calc R . . . .
C7 C 0.1694(2) 0.5862(2) 0.27081(17) 0.0155(3) Uani 1 1 d . . . . .
C8 C 0.0222(2) 0.6046(2) 0.17247(18) 0.0208(3) Uani 1 1 d . . . . .
H8 H -0.044326 0.518263 0.141712 0.025 Uiso 1 1 calc R . . . .
C9 C -0.0284(2) 0.7492(3) 0.11875(19) 0.0259(4) Uani 1 1 d . . . . .
H9 H -0.129569 0.761436 0.052819 0.031 Uiso 1 1 calc R . . . .
C10 C 0.0704(3) 0.8754(2) 0.1623(2) 0.0251(4) Uani 1 1 d . . . . .
H10 H 0.037422 0.973604 0.125061 0.030 Uiso 1 1 calc R . . . .
C11 C 0.6413(2) 0.3880(2) 0.01639(19) 0.0237(4) Uani 1 1 d . . . . .
H11 H 0.640949 0.432940 -0.063660 0.028 Uiso 1 1 calc R . . . .
C12 C 0.5362(2) 0.4386(2) 0.07404(17) 0.0202(3) Uani 1 1 d . . . . .
H12 H 0.462653 0.517177 0.033587 0.024 Uiso 1 1 calc R . . . .
C13 C 0.23729(19) 0.2834(2) 0.56874(17) 0.0155(3) Uani 1 1 d . . . . .
C14 C 0.3340(2) 0.2838(2) 0.71702(18) 0.0213(3) Uani 1 1 d . . . . .
H14A H 0.336702 0.387767 0.751984 0.032 Uiso 1 1 calc GR . . . .
H14B H 0.441397 0.249716 0.731156 0.032 Uiso 1 1 calc GR . . . .
H14C H 0.285626 0.214276 0.762736 0.032 Uiso 1 1 calc GR . . . .
C15 C 0.2409(2) 0.1255(2) 0.5101(2) 0.0240(4) Uani 1 1 d . . . . .
H15A H 0.200820 0.049296 0.556778 0.036 Uiso 1 1 calc GR . . . .
H15B H 0.349236 0.099739 0.519598 0.036 Uiso 1 1 calc GR . . . .
H15C H 0.174880 0.125895 0.416256 0.036 Uiso 1 1 calc GR . . . .
C16 C 0.0687(2) 0.3323(3) 0.5456(2) 0.0302(5) Uani 1 1 d . . . . .
H16A H 0.009163 0.336811 0.450449 0.045 Uiso 1 1 calc GR . . . .
H16B H 0.068985 0.433644 0.584685 0.045 Uiso 1 1 calc GR . . . .
H16C H 0.019600 0.257975 0.586820 0.045 Uiso 1 1 calc GR . . . .
C17 C 0.2167(2) 0.8572(2) 0.26015(19) 0.0214(4) Uani 1 1 d . . . . .
H17 H 0.283603 0.943432 0.290212 0.026 Uiso 1 1 calc R . . . .
C18 C 0.2662(2) 0.7137(2) 0.31460(17) 0.0168(3) Uani 1 1 d . . . . .
H18 H 0.366476 0.702506 0.382002 0.020 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 C6 1.8345(16) . ?
S1 C13 1.8378(17) . ?
O1 C4 1.408(2) . ?
O1 C5 1.359(2) . ?
O2 C5 1.201(2) . ?
C1 H1 0.9500 . ?
C1 C2 1.384(3) . ?
C1 C11 1.390(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.398(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.377(3) . ?
C4 C12 1.382(2) . ?
C5 C6 1.517(2) . ?
C6 H6 1.0000 . ?
C6 C7 1.516(3) . ?
C7 C8 1.393(2) . ?
C7 C18 1.394(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.397(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.393(3) . ?
C10 H10 0.9500 . ?
C10 C17 1.385(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.385(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.533(3) . ?
C13 C15 1.522(3) . ?
C13 C16 1.524(2) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17 0.9500 . ?
C17 C18 1.390(2) . ?
C18 H18 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
C6 S1 C13 103.57(8) . . ?
C5 O1 C4 117.70(14) . . ?
C2 C1 H1 120.1 . . ?
C2 C1 C11 119.80(18) . . ?
C11 C1 H1 120.1 . . ?
C1 C2 H2 119.6 . . ?
C1 C2 C3 120.72(18) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 H3 121.0 . . ?
C4 C3 C2 118.03(17) . . ?
C4 C3 H3 121.0 . . ?
C3 C4 O1 120.16(16) . . ?
C3 C4 C12 122.35(17) . . ?
C12 C4 O1 117.35(16) . . ?
O1 C5 C6 111.03(14) . . ?
O2 C5 O1 124.05(17) . . ?
O2 C5 C6 124.93(17) . . ?
S1 C6 H6 107.6 . . ?
C5 C6 S1 107.86(11) . . ?
C5 C6 H6 107.6 . . ?
C7 C6 S1 113.17(12) . . ?
C7 C6 C5 112.85(13) . . ?
C7 C6 H6 107.6 . . ?
C8 C7 C6 118.90(15) . . ?
C8 C7 C18 119.17(17) . . ?
C18 C7 C6 121.90(15) . . ?
C7 C8 H8 119.7 . . ?
C7 C8 C9 120.51(18) . . ?
C9 C8 H8 119.7 . . ?
C8 C9 H9 120.2 . . ?
C10 C9 C8 119.69(18) . . ?
C10 C9 H9 120.2 . . ?
C9 C10 H10 120.1 . . ?
C17 C10 C9 119.86(17) . . ?
C17 C10 H10 120.1 . . ?
C1 C11 H11 119.9 . . ?
C12 C11 C1 120.20(18) . . ?
C12 C11 H11 119.9 . . ?
C4 C12 C11 118.89(18) . . ?
C4 C12 H12 120.6 . . ?
C11 C12 H12 120.6 . . ?
C14 C13 S1 103.37(12) . . ?
C15 C13 S1 110.92(12) . . ?
C15 C13 C14 110.47(15) . . ?
C15 C13 C16 110.73(17) . . ?
C16 C13 S1 111.13(14) . . ?
C16 C13 C14 110.00(14) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
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 . . ?
C10 C17 H17 119.8 . . ?
C10 C17 C18 120.43(18) . . ?
C18 C17 H17 119.8 . . ?
C7 C18 H18 119.8 . . ?
C17 C18 C7 120.33(17) . . ?
C17 C18 H18 119.8 . . ?

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
S1 C6 C7 C8 -144.27(14) . . . . ?
S1 C6 C7 C18 37.58(19) . . . . ?
O1 C4 C12 C11 175.86(16) . . . . ?
O1 C5 C6 S1 -72.27(16) . . . . ?
O1 C5 C6 C7 53.48(18) . . . . ?
O2 C5 C6 S1 107.83(18) . . . . ?
O2 C5 C6 C7 -126.41(19) . . . . ?
C1 C2 C3 C4 0.2(3) . . . . ?
C1 C11 C12 C4 0.8(3) . . . . ?
C2 C1 C11 C12 -1.3(3) . . . . ?
C2 C3 C4 O1 -176.25(17) . . . . ?
C2 C3 C4 C12 -0.7(3) . . . . ?
C3 C4 C12 C11 0.2(3) . . . . ?
C4 O1 C5 O2 -1.6(3) . . . . ?
C4 O1 C5 C6 178.53(14) . . . . ?
C5 O1 C4 C3 -73.9(2) . . . . ?
C5 O1 C4 C12 110.34(18) . . . . ?
C5 C6 C7 C8 92.89(18) . . . . ?
C5 C6 C7 C18 -85.27(19) . . . . ?
C6 S1 C13 C14 -179.29(11) . . . . ?
C6 S1 C13 C15 62.31(14) . . . . ?
C6 S1 C13 C16 -61.34(15) . . . . ?
C6 C7 C8 C9 -178.53(15) . . . . ?
C6 C7 C18 C17 177.74(15) . . . . ?
C7 C8 C9 C10 1.1(3) . . . . ?
C8 C7 C18 C17 -0.4(3) . . . . ?
C8 C9 C10 C17 -1.1(3) . . . . ?
C9 C10 C17 C18 0.4(3) . . . . ?
C10 C17 C18 C7 0.4(3) . . . . ?
C11 C1 C2 C3 0.8(3) . . . . ?
C13 S1 C6 C5 -106.97(13) . . . . ?
C13 S1 C6 C7 127.46(12) . . . . ?
C18 C7 C8 C9 -0.3(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
