# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

####################################################################### 
# 
# 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_a_a
_database_code_depnum_ccdc_archive 'CCDC 2330166'
loop_
_audit_author_name
_audit_author_address
'Yue Zhao'
;Nanjing University
China
;
_audit_update_record             
;
2024-02-01 deposited with the CCDC.	2024-05-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H20 N2 O3 S'
_chemical_formula_weight         320.40

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'
N N 0.0061 0.0033 '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'

_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                   8.3337(6)
_cell_length_b                   8.9410(6)
_cell_length_c                   11.3827(8)
_cell_angle_alpha                89.680(3)
_cell_angle_beta                 75.307(2)
_cell_angle_gamma                81.963(3)
_cell_volume                     811.95(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4865
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      27.55

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_F_000             340
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.213
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\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            7501
_diffrn_reflns_av_unetI/netI     0.0518
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.302
_diffrn_reflns_theta_max         27.553
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.981
_reflns_number_total             3664
_reflns_number_gt                3259
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0529P)²+0.2134P] 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_number_reflns         3664
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_ref         0.1191
_refine_ls_wR_factor_gt          0.1146
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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 0.56622(5) 0.26231(4) 0.36090(4) 0.04202(14) Uani 1 1 d . . . . .
O1 O 0.88424(13) 0.29537(12) 0.25980(11) 0.0449(3) Uani 1 1 d . . . . .
O3 O 0.85198(14) 1.05301(13) 0.80800(10) 0.0465(3) Uani 1 1 d . . . . .
O2 O 0.67387(15) 1.10999(13) 0.68892(12) 0.0515(3) Uani 1 1 d . . . . .
N3 N 0.67992(14) 0.50318(13) 0.27902(11) 0.0323(3) Uani 1 1 d . . . . .
N1 N 0.89175(15) 0.91505(13) 0.64081(11) 0.0356(3) Uani 1 1 d . . . . .
H1 H 0.977213 0.873968 0.664651 0.043 Uiso 1 1 calc R U . . .
C14 C 0.50795(17) 0.54385(16) 0.32617(13) 0.0352(3) Uani 1 1 d . . . . .
H14 H 0.453337 0.641787 0.325241 0.042 Uiso 1 1 calc R U . . .
C4 C 0.86814(17) 0.85237(15) 0.53479(13) 0.0324(3) Uani 1 1 d . . . . .
C16 C 0.73748(18) 0.35485(15) 0.29151(12) 0.0342(3) Uani 1 1 d . . . . .
C5 C 0.82714(17) 0.70283(15) 0.32917(13) 0.0341(3) Uani 1 1 d . . . . .
C6 C 0.97844(17) 0.72330(16) 0.48281(14) 0.0368(3) Uani 1 1 d . . . . .
H6 H 1.066696 0.686622 0.516125 0.044 Uiso 1 1 calc R U . . .
C7 C 0.74236(18) 0.90971(15) 0.47921(14) 0.0367(3) Uani 1 1 d . . . . .
H7 H 0.671207 0.998047 0.509994 0.044 Uiso 1 1 calc R U . . .
C8 C 0.95720(18) 0.65005(16) 0.38248(13) 0.0367(3) Uani 1 1 d . . . . .
H8 H 1.030933 0.563868 0.349738 0.044 Uiso 1 1 calc R U . . .
C10 C 0.79857(17) 0.61004(16) 0.22726(13) 0.0346(3) Uani 1 1 d . . . . .
H10 H 0.906119 0.548661 0.189173 0.042 Uiso 1 1 calc R U . . .
C15 C 0.42913(19) 0.42850(17) 0.37284(14) 0.0391(3) Uani 1 1 d . . . . .
H15 H 0.314381 0.436699 0.407536 0.047 Uiso 1 1 calc R U . . .
C3 C 0.79462(18) 1.03322(16) 0.70971(14) 0.0378(3) Uani 1 1 d . . . . .
C9 C 0.72312(18) 0.83538(16) 0.37820(14) 0.0375(3) Uani 1 1 d . . . . .
H9 H 0.638581 0.875005 0.342198 0.045 Uiso 1 1 calc R U . . .
C11 C 0.7426(2) 0.69950(17) 0.12621(14) 0.0403(3) Uani 1 1 d . . . . .
H11A H 0.635190 0.760636 0.160560 0.048 Uiso 1 1 calc R U . . .
H11B H 0.822951 0.767383 0.093319 0.048 Uiso 1 1 calc R U . . .
C12 C 0.7266(2) 0.5990(2) 0.02348(15) 0.0514(4) Uani 1 1 d . . . . .
H12A H 0.631260 0.545581 0.052701 0.062 Uiso 1 1 calc R U . . .
H12B H 0.826208 0.524352 -0.000163 0.062 Uiso 1 1 calc R U . . .
C13 C 0.7044(3) 0.6871(3) -0.08751(17) 0.0640(5) Uani 1 1 d . . . . .
H13A H 0.605763 0.761076 -0.064842 0.096 Uiso 1 1 calc R U . . .
H13B H 0.692848 0.618911 -0.148694 0.096 Uiso 1 1 calc R U . . .
H13C H 0.800555 0.736982 -0.118971 0.096 Uiso 1 1 calc R U . . .
C2 C 0.7625(3) 1.1763(2) 0.89075(18) 0.0623(5) Uani 1 1 d . . . . .
H2A H 0.644422 1.188864 0.892488 0.075 Uiso 1 1 calc R U . . .
H2B H 0.805417 1.269435 0.863530 0.075 Uiso 1 1 calc R U . . .
C1 C 0.7838(3) 1.1441(3) 1.01302(19) 0.0712(6) Uani 1 1 d . . . . .
H1A H 0.738061 1.053520 1.040546 0.107 Uiso 1 1 calc R U . . .
H1B H 0.726344 1.226944 1.067778 0.107 Uiso 1 1 calc R U . . .
H1C H 0.900925 1.130603 1.010632 0.107 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 C15 1.7264(15) . ?
S1 C16 1.7597(15) . ?
O1 C16 1.2269(17) . ?
O3 C3 1.3449(19) . ?
O3 C2 1.4437(19) . ?
O2 C3 1.2107(18) . ?
N3 C16 1.3652(17) . ?
N3 C14 1.3931(17) . ?
N3 C10 1.4832(17) . ?
N1 C3 1.3546(18) . ?
N1 C4 1.4027(19) . ?
N1 H1 0.8600 . ?
C14 C15 1.336(2) . ?
C14 H14 0.9300 . ?
C4 C7 1.394(2) . ?
C4 C6 1.4007(19) . ?
C5 C9 1.3936(19) . ?
C5 C8 1.398(2) . ?
C5 C10 1.516(2) . ?
C6 C8 1.381(2) . ?
C6 H6 0.9300 . ?
C7 C9 1.386(2) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C10 C11 1.529(2) . ?
C10 H10 0.9800 . ?
C15 H15 0.9300 . ?
C9 H9 0.9300 . ?
C11 C12 1.522(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.522(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C2 C1 1.469(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 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
C15 S1 C16 91.36(7) . . ?
C3 O3 C2 116.23(13) . . ?
C16 N3 C14 114.65(12) . . ?
C16 N3 C10 120.47(11) . . ?
C14 N3 C10 124.72(11) . . ?
C3 N1 C4 127.09(12) . . ?
C3 N1 H1 116.5 . . ?
C4 N1 H1 116.5 . . ?
C15 C14 N3 113.45(13) . . ?
C15 C14 H14 123.3 . . ?
N3 C14 H14 123.3 . . ?
C7 C4 C6 118.56(14) . . ?
C7 C4 N1 124.27(12) . . ?
C6 C4 N1 117.18(12) . . ?
O1 C16 N3 125.84(14) . . ?
O1 C16 S1 125.41(11) . . ?
N3 C16 S1 108.75(10) . . ?
C9 C5 C8 117.55(14) . . ?
C9 C5 C10 123.06(13) . . ?
C8 C5 C10 119.28(12) . . ?
C8 C6 C4 120.54(13) . . ?
C8 C6 H6 119.7 . . ?
C4 C6 H6 119.7 . . ?
C9 C7 C4 120.16(13) . . ?
C9 C7 H7 119.9 . . ?
C4 C7 H7 119.9 . . ?
C6 C8 C5 121.33(13) . . ?
C6 C8 H8 119.3 . . ?
C5 C8 H8 119.3 . . ?
N3 C10 C5 109.49(11) . . ?
N3 C10 C11 110.69(12) . . ?
C5 C10 C11 116.01(12) . . ?
N3 C10 H10 106.7 . . ?
C5 C10 H10 106.7 . . ?
C11 C10 H10 106.7 . . ?
C14 C15 S1 111.75(11) . . ?
C14 C15 H15 124.1 . . ?
S1 C15 H15 124.1 . . ?
O2 C3 O3 124.13(14) . . ?
O2 C3 N1 126.61(15) . . ?
O3 C3 N1 109.26(12) . . ?
C7 C9 C5 121.73(13) . . ?
C7 C9 H9 119.1 . . ?
C5 C9 H9 119.1 . . ?
C12 C11 C10 113.02(13) . . ?
C12 C11 H11A 109.0 . . ?
C10 C11 H11A 109.0 . . ?
C12 C11 H11B 109.0 . . ?
C10 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
C11 C12 C13 112.90(16) . . ?
C11 C12 H12A 109.0 . . ?
C13 C12 H12A 109.0 . . ?
C11 C12 H12B 109.0 . . ?
C13 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O3 C2 C1 109.39(16) . . ?
O3 C2 H2A 109.8 . . ?
C1 C2 H2A 109.8 . . ?
O3 C2 H2B 109.8 . . ?
C1 C2 H2B 109.8 . . ?
H2A C2 H2B 108.2 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?

_refine_diff_density_max         0.235
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.041



