# 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_201026aa_a
_database_code_depnum_ccdc_archive 'CCDC 2082637'
loop_
_audit_author_name
_audit_author_address
'Fusheng He'
;Taizhou University
China
;
_audit_update_record             
;
2021-05-10 deposited with the CCDC.	2021-06-23 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            'C19 H25 N O3 S'
_chemical_formula_weight         347.46

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'
N N 0.0241 0.0134 '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      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

_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, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   8.4398(7)
_cell_length_b                   19.8446(15)
_cell_length_c                   10.8335(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1814.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1261
_cell_measurement_theta_min      3.88
_cell_measurement_theta_max      29.98

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_F_000             744
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    1.121
_shelx_estimated_absorpt_T_min   0.767
_shelx_estimated_absorpt_T_max   0.957
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.633
_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            27688
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.954
_diffrn_reflns_theta_max         58.440
_diffrn_reflns_theta_full        53.594
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3898
_reflns_number_gt                3771
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.889
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    0.996

_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)+(0.0332P)²+0.2460P] 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 1732 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.013(7)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3898
_refine_ls_number_parameters     220
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0254
_refine_ls_R_factor_gt           0.0241
_refine_ls_wR_factor_ref         0.0627
_refine_ls_wR_factor_gt          0.0617
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.001
_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 0.79475(4) 0.34505(2) 0.51213(4) 0.02017(10) Uani 1 1 d . . . . .
N1 N 0.8281(3) 0.14807(12) 0.1364(2) 0.0538(6) Uani 1 1 d . . . . .
O1 O 0.13950(19) 0.27141(7) 0.86303(12) 0.0322(3) Uani 1 1 d . . . . .
O2 O 0.89526(16) 0.38831(7) 0.43962(14) 0.0317(3) Uani 1 1 d . . . . .
O3 O 0.84856(16) 0.32697(7) 0.63449(13) 0.0292(3) Uani 1 1 d . . . . .
C1 C 0.0508(2) 0.07225(10) 0.76392(18) 0.0285(4) Uani 1 1 d . . . . .
C2 C 0.0731(2) 0.13970(10) 0.79435(17) 0.0244(4) Uani 1 1 d . . . . .
H2 H 0.027456 0.156792 0.868119 0.029 Uiso 1 1 calc R U . . .
C3 C 0.1611(2) 0.18289(9) 0.71903(17) 0.0216(3) Uani 1 1 d . . . . .
C4 C 0.2285(2) 0.15773(10) 0.61109(18) 0.0273(4) Uani 1 1 d . . . . .
H4 H 0.288078 0.186571 0.558691 0.033 Uiso 1 1 calc R U . . .
C5 C 0.2084(3) 0.09025(11) 0.5803(2) 0.0334(5) Uani 1 1 d . . . . .
H5 H 0.255020 0.072913 0.507086 0.040 Uiso 1 1 calc R U . . .
C6 C 0.1206(3) 0.04824(9) 0.6560(2) 0.0335(5) Uani 1 1 d . . . . .
H6 H 0.107626 0.002232 0.633929 0.040 Uiso 1 1 calc R U . . .
C7 C 0.1817(2) 0.25478(9) 0.75947(16) 0.0208(3) Uani 1 1 d . . . . .
C8 C 0.2571(2) 0.30423(9) 0.67174(16) 0.0218(3) Uani 1 1 d . . . . .
H8A H 0.187910 0.309772 0.598636 0.026 Uiso 1 1 calc R U . . .
H8B H 0.359796 0.285883 0.643117 0.026 Uiso 1 1 calc R U . . .
C9 C 0.28455(19) 0.37293(8) 0.73114(15) 0.0184(3) Uani 1 1 d . . . . .
H9A H 0.341809 0.366160 0.809921 0.022 Uiso 1 1 calc R U . . .
H9B H 0.180254 0.393002 0.751079 0.022 Uiso 1 1 calc R U . . .
C10 C 0.37880(19) 0.42374(8) 0.65185(14) 0.0171(3) Uani 1 1 d . . . . .
C11 C 0.54053(19) 0.39359(8) 0.62956(15) 0.0179(3) Uani 1 1 d . . . . .
H11 H 0.601772 0.383039 0.700550 0.021 Uiso 1 1 calc R U . . .
C12 C 0.60547(19) 0.38041(8) 0.52121(17) 0.0206(3) Uani 1 1 d . . . . .
H12 H 0.548769 0.390233 0.447627 0.025 Uiso 1 1 calc R U . . .
C13 C 0.7648(2) 0.26966(9) 0.42575(18) 0.0234(4) Uani 1 1 d . . . . .
H13A H 0.686796 0.240435 0.468137 0.028 Uiso 1 1 calc R U . . .
H13B H 0.723265 0.280642 0.342684 0.028 Uiso 1 1 calc R U . . .
C14 C 0.9232(2) 0.23328(11) 0.4146(2) 0.0347(5) Uani 1 1 d . . . . .
H14A H 0.974821 0.232286 0.496640 0.042 Uiso 1 1 calc R U . . .
H14B H 0.992716 0.259054 0.358106 0.042 Uiso 1 1 calc R U . . .
C15 C 0.9077(3) 0.16096(11) 0.3665(2) 0.0355(5) Uani 1 1 d . . . . .
H15A H 1.010691 0.137850 0.377684 0.043 Uiso 1 1 calc R U . . .
H15B H 0.828597 0.136976 0.417681 0.043 Uiso 1 1 calc R U . . .
C16 C 0.8611(3) 0.15508(10) 0.2373(2) 0.0339(5) Uani 1 1 d . . . . .
C17 C -0.0434(3) 0.02648(12) 0.8462(2) 0.0424(5) Uani 1 1 d . . . . .
H17A H 0.027971 -0.005502 0.886890 0.064 Uiso 1 1 calc R U . . .
H17B H -0.121188 0.001711 0.796646 0.064 Uiso 1 1 calc R U . . .
H17C H -0.098606 0.053346 0.908742 0.064 Uiso 1 1 calc R U . . .
C18 C 0.3996(2) 0.48850(9) 0.72878(17) 0.0228(3) Uani 1 1 d . . . . .
H18A H 0.463448 0.478582 0.802100 0.034 Uiso 1 1 calc R U . . .
H18B H 0.295357 0.505256 0.754288 0.034 Uiso 1 1 calc R U . . .
H18C H 0.453070 0.522817 0.678850 0.034 Uiso 1 1 calc R U . . .
C19 C 0.2921(2) 0.43991(9) 0.53165(17) 0.0237(4) Uani 1 1 d . . . . .
H19A H 0.184801 0.455816 0.550426 0.036 Uiso 1 1 calc R U . . .
H19B H 0.285877 0.399223 0.480612 0.036 Uiso 1 1 calc R U . . .
H19C H 0.349853 0.475061 0.486826 0.036 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 1.4400(14) . ?
S1 O3 1.4465(14) . ?
S1 C12 1.7475(16) . ?
S1 C13 1.7828(18) . ?
N1 C16 1.136(3) . ?
O1 C7 1.222(2) . ?
C1 C2 1.391(3) . ?
C1 C6 1.393(3) . ?
C1 C17 1.501(3) . ?
C2 C3 1.397(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.393(3) . ?
C3 C7 1.502(2) . ?
C4 C5 1.390(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.384(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.507(2) . ?
C8 C9 1.525(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.545(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.510(2) . ?
C10 C19 1.528(2) . ?
C10 C18 1.542(2) . ?
C11 C12 1.322(2) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.524(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.533(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.458(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?

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 O3 117.57(9) . . ?
O2 S1 C12 109.26(8) . . ?
O3 S1 C12 109.57(8) . . ?
O2 S1 C13 107.32(9) . . ?
O3 S1 C13 108.50(9) . . ?
C12 S1 C13 103.69(9) . . ?
C2 C1 C6 118.08(17) . . ?
C2 C1 C17 120.89(19) . . ?
C6 C1 C17 121.02(19) . . ?
C1 C2 C3 121.59(18) . . ?
C1 C2 H2 119.2 . . ?
C3 C2 H2 119.2 . . ?
C4 C3 C2 119.17(16) . . ?
C4 C3 C7 122.54(16) . . ?
C2 C3 C7 118.28(16) . . ?
C5 C4 C3 119.78(19) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C6 C5 C4 120.2(2) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C1 121.15(18) . . ?
C5 C6 H6 119.4 . . ?
C1 C6 H6 119.4 . . ?
O1 C7 C3 119.36(16) . . ?
O1 C7 C8 121.74(16) . . ?
C3 C7 C8 118.89(15) . . ?
C7 C8 C9 112.34(14) . . ?
C7 C8 H8A 109.1 . . ?
C9 C8 H8A 109.1 . . ?
C7 C8 H8B 109.1 . . ?
C9 C8 H8B 109.1 . . ?
H8A C8 H8B 107.9 . . ?
C8 C9 C10 115.28(13) . . ?
C8 C9 H9A 108.5 . . ?
C10 C9 H9A 108.5 . . ?
C8 C9 H9B 108.5 . . ?
C10 C9 H9B 108.5 . . ?
H9A C9 H9B 107.5 . . ?
C11 C10 C19 112.34(13) . . ?
C11 C10 C18 108.30(13) . . ?
C19 C10 C18 109.88(14) . . ?
C11 C10 C9 107.21(13) . . ?
C19 C10 C9 111.36(13) . . ?
C18 C10 C9 107.58(13) . . ?
C12 C11 C10 126.55(15) . . ?
C12 C11 H11 116.7 . . ?
C10 C11 H11 116.7 . . ?
C11 C12 S1 120.57(14) . . ?
C11 C12 H12 119.7 . . ?
S1 C12 H12 119.7 . . ?
C14 C13 S1 108.33(13) . . ?
C14 C13 H13A 110.0 . . ?
S1 C13 H13A 110.0 . . ?
C14 C13 H13B 110.0 . . ?
S1 C13 H13B 110.0 . . ?
H13A C13 H13B 108.4 . . ?
C13 C14 C15 113.30(17) . . ?
C13 C14 H14A 108.9 . . ?
C15 C14 H14A 108.9 . . ?
C13 C14 H14B 108.9 . . ?
C15 C14 H14B 108.9 . . ?
H14A C14 H14B 107.7 . . ?
C16 C15 C14 115.10(19) . . ?
C16 C15 H15A 108.5 . . ?
C14 C15 H15A 108.5 . . ?
C16 C15 H15B 108.5 . . ?
C14 C15 H15B 108.5 . . ?
H15A C15 H15B 107.5 . . ?
N1 C16 C15 177.2(2) . . ?
C1 C17 H17A 109.5 . . ?
C1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C10 C18 H18A 109.5 . . ?
C10 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C10 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C10 C19 H19A 109.5 . . ?
C10 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C10 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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(3) . . . . ?
C17 C1 C2 C3 179.72(19) . . . . ?
C1 C2 C3 C4 -0.2(3) . . . . ?
C1 C2 C3 C7 -179.09(17) . . . . ?
C2 C3 C4 C5 -0.4(3) . . . . ?
C7 C3 C4 C5 178.40(19) . . . . ?
C3 C4 C5 C6 0.5(3) . . . . ?
C4 C5 C6 C1 0.0(3) . . . . ?
C2 C1 C6 C5 -0.6(3) . . . . ?
C17 C1 C6 C5 -179.6(2) . . . . ?
C4 C3 C7 O1 -169.50(19) . . . . ?
C2 C3 C7 O1 9.3(3) . . . . ?
C4 C3 C7 C8 9.3(3) . . . . ?
C2 C3 C7 C8 -171.90(17) . . . . ?
O1 C7 C8 C9 4.6(3) . . . . ?
C3 C7 C8 C9 -174.18(15) . . . . ?
C7 C8 C9 C10 173.27(14) . . . . ?
C8 C9 C10 C11 -61.62(18) . . . . ?
C8 C9 C10 C19 61.63(18) . . . . ?
C8 C9 C10 C18 -177.91(14) . . . . ?
C19 C10 C11 C12 -1.1(2) . . . . ?
C18 C10 C11 C12 -122.61(18) . . . . ?
C9 C10 C11 C12 121.58(18) . . . . ?
C10 C11 C12 S1 -179.82(13) . . . . ?
O2 S1 C12 C11 -123.02(15) . . . . ?
O3 S1 C12 C11 7.11(17) . . . . ?
C13 S1 C12 C11 122.79(15) . . . . ?
O2 S1 C13 C14 65.81(16) . . . . ?
O3 S1 C13 C14 -62.19(16) . . . . ?
C12 S1 C13 C14 -178.62(14) . . . . ?
S1 C13 C14 C15 167.81(16) . . . . ?
C13 C14 C15 C16 69.6(3) . . . . ?

_refine_diff_density_max         0.182
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.033

