# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_ga_21013a_a
_database_code_depnum_ccdc_archive 'CCDC 2062342'
loop_
_audit_author_name
_audit_author_address
'Jun Zhang'
;Shanghai Institute of Organic Chemistry Shanghai
China
;
_audit_update_record             
;
2021-02-10 deposited with the CCDC.	2021-04-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H18 O3 S'
_chemical_formula_weight         278.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.2925 0.4295 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   13.5251(14)
_cell_length_b                   10.9872(11)
_cell_length_c                   9.4818(9)
_cell_angle_alpha                90
_cell_angle_beta                 100.546(4)
_cell_angle_gamma                90
_cell_volume                     1385.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    601
_cell_measurement_theta_min      4.54
_cell_measurement_theta_max      29.10

_exptl_crystal_description       bolck
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    1.369
_shelx_estimated_absorpt_T_min   0.709
_shelx_estimated_absorpt_T_max   0.898
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.634
_exptl_absorpt_correction_T_max  0.752
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.34138
_diffrn_radiation_type           GaK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10335
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.542
_diffrn_reflns_theta_max         58.479
_diffrn_reflns_theta_full        53.594
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 0.977
_reflns_number_total             2899
_reflns_number_gt                2833
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.950
_reflns_Friedel_fraction_max     0.952
_reflns_Friedel_fraction_full    0.956

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0279P)²+0.2556P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1349 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.032(7)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2899
_refine_ls_number_parameters     174
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0240
_refine_ls_R_factor_gt           0.0233
_refine_ls_wR_factor_ref         0.0591
_refine_ls_wR_factor_gt          0.0587
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_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_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 0.37739(3) 0.34925(4) 0.39531(4) 0.01839(12) Uani 1 1 d . . . . .
O1 O 0.29571(11) 0.28610(14) 0.44293(15) 0.0296(3) Uani 1 1 d . . . . .
O2 O 0.40000(11) 0.47137(12) 0.44697(16) 0.0280(3) Uani 1 1 d . . . . .
O3 O 0.48045(15) 0.02897(13) 0.61215(17) 0.0397(4) Uani 1 1 d . . . . .
C1 C 0.48984(14) 0.25736(16) 0.44980(19) 0.0182(3) Uani 1 1 d . . . . .
H1 H 0.474833 0.174290 0.408280 0.022 Uiso 1 1 calc R U . . .
C2 C 0.35228(15) 0.35361(17) 0.2028(2) 0.0221(4) Uani 1 1 d . . . . .
H2 H 0.411554 0.389991 0.168893 0.027 Uiso 1 1 calc R U . . .
C3 C 0.26206(18) 0.4368(2) 0.1595(3) 0.0377(5) Uani 1 1 d . . . . .
H3A H 0.249433 0.448349 0.055219 0.056 Uiso 1 1 calc R U . . .
H3B H 0.275787 0.515818 0.207043 0.056 Uiso 1 1 calc R U . . .
H3C H 0.202807 0.399996 0.188208 0.056 Uiso 1 1 calc R U . . .
C4 C 0.33373(19) 0.2272(2) 0.1396(2) 0.0359(5) Uani 1 1 d . . . . .
H4A H 0.280203 0.187607 0.179854 0.054 Uiso 1 1 calc R U . . .
H4B H 0.395550 0.179024 0.162823 0.054 Uiso 1 1 calc R U . . .
H4C H 0.313434 0.233203 0.035157 0.054 Uiso 1 1 calc R U . . .
C5 C 0.50465(14) 0.24500(17) 0.61031(18) 0.0188(4) Uani 1 1 d . . . . .
C6 C 0.49898(15) 0.12376(18) 0.6766(2) 0.0232(4) Uani 1 1 d . . . . .
C7 C 0.52046(18) 0.13962(19) 0.8375(2) 0.0282(4) Uani 1 1 d . . . . .
H7A H 0.583913 0.098273 0.880333 0.034 Uiso 1 1 calc R U . . .
H7B H 0.465065 0.105645 0.880636 0.034 Uiso 1 1 calc R U . . .
C8 C 0.52922(19) 0.27669(19) 0.8618(2) 0.0321(5) Uani 1 1 d . . . . .
H8A H 0.474765 0.306958 0.909580 0.038 Uiso 1 1 calc R U . . .
H8B H 0.594928 0.298050 0.921413 0.038 Uiso 1 1 calc R U . . .
C9 C 0.51983(18) 0.32871(18) 0.7139(2) 0.0281(4) Uani 1 1 d . . . . .
H9 H 0.524263 0.413359 0.695560 0.034 Uiso 1 1 calc R U . . .
C10 C 0.57790(14) 0.30733(17) 0.38847(19) 0.0195(4) Uani 1 1 d . . . . .
C11 C 0.62311(15) 0.41838(18) 0.4325(2) 0.0240(4) Uani 1 1 d . . . . .
H11 H 0.600084 0.464005 0.505189 0.029 Uiso 1 1 calc R U . . .
C12 C 0.70144(17) 0.46298(19) 0.3711(3) 0.0310(5) Uani 1 1 d . . . . .
H12 H 0.731689 0.538803 0.401774 0.037 Uiso 1 1 calc R U . . .
C13 C 0.73552(16) 0.3969(2) 0.2650(2) 0.0346(5) Uani 1 1 d . . . . .
H13 H 0.788136 0.428118 0.221426 0.042 Uiso 1 1 calc R U . . .
C14 C 0.69262(17) 0.2850(2) 0.2226(2) 0.0334(5) Uani 1 1 d . . . . .
H14 H 0.717210 0.238636 0.151769 0.040 Uiso 1 1 calc R U . . .
C15 C 0.61374(16) 0.2404(2) 0.2833(2) 0.0269(4) Uani 1 1 d . . . . .
H15 H 0.584164 0.164136 0.253100 0.032 Uiso 1 1 calc R U . . .


_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 O2 1.4419(14) . ?
S1 O1 1.4451(14) . ?
S1 C2 1.7953(19) . ?
S1 C1 1.8198(19) . ?
O3 C6 1.211(3) . ?
C1 C5 1.504(2) . ?
C1 C10 1.520(2) . ?
C1 H1 1.0000 . ?
C2 C4 1.515(3) . ?
C2 C3 1.520(3) . ?
C2 H2 1.0000 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C9 1.334(3) . ?
C5 C6 1.481(3) . ?
C6 C7 1.510(3) . ?
C7 C8 1.525(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.499(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9 0.9500 . ?
C10 C11 1.394(3) . ?
C10 C15 1.395(3) . ?
C11 C12 1.388(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.386(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.387(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.391(3) . ?
C14 H14 0.9500 . ?
C15 H15 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
O2 S1 O1 117.86(9) . . ?
O2 S1 C2 108.03(9) . . ?
O1 S1 C2 108.50(9) . . ?
O2 S1 C1 107.79(8) . . ?
O1 S1 C1 106.97(9) . . ?
C2 S1 C1 107.23(9) . . ?
C5 C1 C10 116.81(14) . . ?
C5 C1 S1 106.68(12) . . ?
C10 C1 S1 111.32(12) . . ?
C5 C1 H1 107.2 . . ?
C10 C1 H1 107.2 . . ?
S1 C1 H1 107.2 . . ?
C4 C2 C3 112.20(18) . . ?
C4 C2 S1 111.38(14) . . ?
C3 C2 S1 106.49(14) . . ?
C4 C2 H2 108.9 . . ?
C3 C2 H2 108.9 . . ?
S1 C2 H2 108.9 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C9 C5 C6 108.70(16) . . ?
C9 C5 C1 131.04(17) . . ?
C6 C5 C1 120.21(15) . . ?
O3 C6 C5 125.55(18) . . ?
O3 C6 C7 126.40(18) . . ?
C5 C6 C7 108.05(16) . . ?
C6 C7 C8 105.19(16) . . ?
C6 C7 H7A 110.7 . . ?
C8 C7 H7A 110.7 . . ?
C6 C7 H7B 110.7 . . ?
C8 C7 H7B 110.7 . . ?
H7A C7 H7B 108.8 . . ?
C9 C8 C7 104.13(17) . . ?
C9 C8 H8A 110.9 . . ?
C7 C8 H8A 110.9 . . ?
C9 C8 H8B 110.9 . . ?
C7 C8 H8B 110.9 . . ?
H8A C8 H8B 108.9 . . ?
C5 C9 C8 113.67(18) . . ?
C5 C9 H9 123.2 . . ?
C8 C9 H9 123.2 . . ?
C11 C10 C15 118.97(18) . . ?
C11 C10 C1 122.21(16) . . ?
C15 C10 C1 118.82(18) . . ?
C12 C11 C10 120.68(18) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C13 C12 C11 120.0(2) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C14 119.9(2) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C13 C14 C15 120.3(2) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C14 C15 C10 120.2(2) . . ?
C14 C15 H15 119.9 . . ?
C10 C15 H15 119.9 . . ?

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
O2 S1 C1 C5 68.92(14) . . . . ?
O1 S1 C1 C5 -58.75(13) . . . . ?
C2 S1 C1 C5 -174.98(12) . . . . ?
O2 S1 C1 C10 -59.56(15) . . . . ?
O1 S1 C1 C10 172.77(12) . . . . ?
C2 S1 C1 C10 56.54(14) . . . . ?
O2 S1 C2 C4 176.66(16) . . . . ?
O1 S1 C2 C4 -54.49(17) . . . . ?
C1 S1 C2 C4 60.73(17) . . . . ?
O2 S1 C2 C3 -60.71(16) . . . . ?
O1 S1 C2 C3 68.13(16) . . . . ?
C1 S1 C2 C3 -176.65(14) . . . . ?
C10 C1 C5 C9 64.5(3) . . . . ?
S1 C1 C5 C9 -60.7(3) . . . . ?
C10 C1 C5 C6 -118.27(19) . . . . ?
S1 C1 C5 C6 116.52(16) . . . . ?
C9 C5 C6 O3 175.8(2) . . . . ?
C1 C5 C6 O3 -1.9(3) . . . . ?
C9 C5 C6 C7 -4.3(2) . . . . ?
C1 C5 C6 C7 177.98(17) . . . . ?
O3 C6 C7 C8 -175.0(2) . . . . ?
C5 C6 C7 C8 5.1(2) . . . . ?
C6 C7 C8 C9 -4.1(2) . . . . ?
C6 C5 C9 C8 1.6(3) . . . . ?
C1 C5 C9 C8 179.01(19) . . . . ?
C7 C8 C9 C5 1.7(3) . . . . ?
C5 C1 C10 C11 -54.9(2) . . . . ?
S1 C1 C10 C11 67.91(19) . . . . ?
C5 C1 C10 C15 125.91(18) . . . . ?
S1 C1 C10 C15 -111.25(16) . . . . ?
C15 C10 C11 C12 1.1(3) . . . . ?
C1 C10 C11 C12 -178.06(17) . . . . ?
C10 C11 C12 C13 -0.1(3) . . . . ?
C11 C12 C13 C14 -1.4(3) . . . . ?
C12 C13 C14 C15 1.7(3) . . . . ?
C13 C14 C15 C10 -0.7(3) . . . . ?
C11 C10 C15 C14 -0.7(3) . . . . ?
C1 C10 C15 C14 178.46(17) . . . . ?

_refine_diff_density_max         0.215
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.036



