# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2019

####################################################################### 
# 
# 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_81211c_a
_database_code_depnum_ccdc_archive 'CCDC 1899054'
loop_
_audit_author_name
_audit_author_address
'Fusheng He'
;Zhejiang University
China
;
_audit_update_record             
;
2019-02-23 deposited with the CCDC.	2019-04-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H20 O3 S'
_chemical_formula_weight         328.41

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   6.9512(2)
_cell_length_b                   8.6039(3)
_cell_length_c                   15.1128(4)
_cell_angle_alpha                102.3370(10)
_cell_angle_beta                 92.4660(10)
_cell_angle_gamma                108.0020(10)
_cell_volume                     833.95(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9955
_cell_measurement_theta_min      6.04
_cell_measurement_theta_max      59.41

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_F_000             348
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    1.192
_shelx_estimated_absorpt_T_min   0.709
_shelx_estimated_absorpt_T_max   0.832
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.692
_exptl_absorpt_correction_T_max  0.864
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(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            23271
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_av_R_equivalents  0.0558
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         4.926
_diffrn_reflns_theta_max         57.489
_diffrn_reflns_theta_full        53.594
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             3458
_reflns_number_gt                3208
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0646P)²+0.1597P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.044(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3458
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0415
_refine_ls_wR_factor_ref         0.1148
_refine_ls_wR_factor_gt          0.1121
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.002
_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 0.49535(5) 0.41411(4) 0.20157(2) 0.04440(16) Uani 1 1 d . . . . .
O1 O 0.5117(2) 0.69154(18) 0.49830(8) 0.0683(4) Uani 1 1 d . . . . .
O2 O 0.69657(17) 0.42653(14) 0.17787(7) 0.0550(3) Uani 1 1 d . . . . .
O3 O 0.3434(2) 0.25052(14) 0.18293(9) 0.0675(4) Uani 1 1 d . . . . .
C1 C 0.6714(3) 0.69569(19) 0.46998(9) 0.0498(4) Uani 1 1 d . . . . .
C2 C 0.6997(2) 0.64355(17) 0.36779(9) 0.0413(3) Uani 1 1 d . . . . .
C3 C 0.8935(2) 0.5952(2) 0.37638(12) 0.0547(4) Uani 1 1 d . . . . .
H3A H 0.8609 0.4814 0.3845 0.066 Uiso 1 1 calc R U . . .
H3B H 0.9634 0.6027 0.3225 0.066 Uiso 1 1 calc R U . . .
C4 C 1.0248(3) 0.7223(3) 0.46043(13) 0.0677(5) Uani 1 1 d . . . . .
H4A H 1.1237 0.6795 0.4851 0.081 Uiso 1 1 calc R U . . .
H4B H 1.0960 0.8283 0.4459 0.081 Uiso 1 1 calc R U . . .
C5 C 0.8727(3) 0.7435(3) 0.52689(12) 0.0708(5) Uani 1 1 d . . . . .
H5A H 0.8651 0.6709 0.5686 0.085 Uiso 1 1 calc R U . . .
H5B H 0.9119 0.8592 0.5620 0.085 Uiso 1 1 calc R U . . .
C6 C 0.5098(2) 0.49744(18) 0.32160(9) 0.0442(3) Uani 1 1 d . . . . .
H6A H 0.3923 0.5339 0.3326 0.053 Uiso 1 1 calc R U . . .
H6B H 0.4978 0.4063 0.3516 0.053 Uiso 1 1 calc R U . . .
C7 C 0.4002(2) 0.54149(17) 0.14718(8) 0.0408(3) Uani 1 1 d . . . . .
C8 C 0.1977(2) 0.5295(2) 0.14827(10) 0.0514(4) Uani 1 1 d . . . . .
H8 H 0.1129 0.4559 0.1781 0.062 Uiso 1 1 calc R U . . .
C9 C 0.1226(3) 0.6275(2) 0.10476(12) 0.0584(4) Uani 1 1 d . . . . .
H9 H -0.0139 0.6194 0.1056 0.070 Uiso 1 1 calc R U . . .
C10 C 0.2453(3) 0.7379(2) 0.05970(10) 0.0527(4) Uani 1 1 d . . . . .
C11 C 0.4465(3) 0.7452(2) 0.05808(11) 0.0560(4) Uani 1 1 d . . . . .
H11 H 0.5305 0.8167 0.0270 0.067 Uiso 1 1 calc R U . . .
C12 C 0.5256(2) 0.6488(2) 0.10146(10) 0.0505(4) Uani 1 1 d . . . . .
H12 H 0.6616 0.6559 0.1000 0.061 Uiso 1 1 calc R U . . .
C13 C 0.1611(4) 0.8457(3) 0.01337(15) 0.0767(6) Uani 1 1 d . . . . .
H13A H 0.2010 0.9580 0.0512 0.115 Uiso 1 1 calc R U . . .
H13B H 0.0152 0.7995 0.0036 0.115 Uiso 1 1 calc R U . . .
H13C H 0.2136 0.8485 -0.0442 0.115 Uiso 1 1 calc R U . . .
C14 C 0.7271(2) 0.79973(17) 0.32907(9) 0.0435(3) Uani 1 1 d . . . . .
C15 C 0.5801(3) 0.8791(2) 0.33756(12) 0.0608(4) Uani 1 1 d . . . . .
H15 H 0.4696 0.8403 0.3688 0.073 Uiso 1 1 calc R U . . .
C16 C 0.5965(4) 1.0157(3) 0.29988(15) 0.0805(6) Uani 1 1 d . . . . .
H16 H 0.4963 1.0669 0.3057 0.097 Uiso 1 1 calc R U . . .
C17 C 0.7579(4) 1.0755(2) 0.25445(14) 0.0801(6) Uani 1 1 d . . . . .
H17 H 0.7676 1.1667 0.2291 0.096 Uiso 1 1 calc R U . . .
C18 C 0.9060(3) 1.0006(2) 0.24625(12) 0.0722(6) Uani 1 1 d . . . . .
H18 H 1.0168 1.0418 0.2156 0.087 Uiso 1 1 calc R U . . .
C19 C 0.8919(3) 0.8630(2) 0.28342(10) 0.0540(4) Uani 1 1 d . . . . .
H19 H 0.9935 0.8134 0.2776 0.065 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 O3 1.4359(11) . ?
S1 O2 1.4364(11) . ?
S1 C7 1.7608(14) . ?
S1 C6 1.7886(14) . ?
O1 C1 1.200(2) . ?
C1 C5 1.502(2) . ?
C1 C2 1.5522(18) . ?
C2 C6 1.526(2) . ?
C2 C3 1.536(2) . ?
C2 C14 1.5400(18) . ?
C3 C4 1.527(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.514(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.380(2) . ?
C7 C12 1.3845(19) . ?
C8 C9 1.377(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.385(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.382(2) . ?
C10 C13 1.508(2) . ?
C11 C12 1.379(2) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C19 1.388(2) . ?
C14 C15 1.390(2) . ?
C15 C16 1.388(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.362(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.370(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.394(2) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?

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
O3 S1 O2 118.49(8) . . ?
O3 S1 C7 107.72(7) . . ?
O2 S1 C7 109.00(6) . . ?
O3 S1 C6 105.26(7) . . ?
O2 S1 C6 109.09(7) . . ?
C7 S1 C6 106.66(6) . . ?
O1 C1 C5 125.98(14) . . ?
O1 C1 C2 124.79(14) . . ?
C5 C1 C2 109.17(14) . . ?
C6 C2 C3 114.48(12) . . ?
C6 C2 C14 112.37(11) . . ?
C3 C2 C14 114.19(12) . . ?
C6 C2 C1 107.51(11) . . ?
C3 C2 C1 100.29(11) . . ?
C14 C2 C1 106.73(11) . . ?
C4 C3 C2 104.94(13) . . ?
C4 C3 H3A 110.8 . . ?
C2 C3 H3A 110.8 . . ?
C4 C3 H3B 110.8 . . ?
C2 C3 H3B 110.8 . . ?
H3A C3 H3B 108.8 . . ?
C5 C4 C3 103.79(15) . . ?
C5 C4 H4A 111.0 . . ?
C3 C4 H4A 111.0 . . ?
C5 C4 H4B 111.0 . . ?
C3 C4 H4B 111.0 . . ?
H4A C4 H4B 109.0 . . ?
C1 C5 C4 106.02(14) . . ?
C1 C5 H5A 110.5 . . ?
C4 C5 H5A 110.5 . . ?
C1 C5 H5B 110.5 . . ?
C4 C5 H5B 110.5 . . ?
H5A C5 H5B 108.7 . . ?
C2 C6 S1 117.68(9) . . ?
C2 C6 H6A 107.9 . . ?
S1 C6 H6A 107.9 . . ?
C2 C6 H6B 107.9 . . ?
S1 C6 H6B 107.9 . . ?
H6A C6 H6B 107.2 . . ?
C8 C7 C12 120.34(14) . . ?
C8 C7 S1 119.27(11) . . ?
C12 C7 S1 120.36(11) . . ?
C9 C8 C7 119.32(14) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C8 C9 C10 121.55(15) . . ?
C8 C9 H9 119.2 . . ?
C10 C9 H9 119.2 . . ?
C11 C10 C9 118.01(15) . . ?
C11 C10 C13 121.13(16) . . ?
C9 C10 C13 120.85(17) . . ?
C12 C11 C10 121.52(14) . . ?
C12 C11 H11 119.2 . . ?
C10 C11 H11 119.2 . . ?
C11 C12 C7 119.24(14) . . ?
C11 C12 H12 120.4 . . ?
C7 C12 H12 120.4 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C19 C14 C15 118.05(14) . . ?
C19 C14 C2 122.44(13) . . ?
C15 C14 C2 119.49(13) . . ?
C16 C15 C14 120.72(18) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C17 C16 C15 120.6(2) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C16 C17 C18 119.66(17) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 H17 120.2 . . ?
C17 C18 C19 120.54(18) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
C14 C19 C18 120.39(18) . . ?
C14 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?

_refine_diff_density_max         0.495
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.049



