# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_exp_12603
_database_code_depnum_ccdc_archive 'CCDC 2247237'
loop_
_audit_author_name
_audit_author_address
'Pengfei Zhou'
;Guangxi university
China
;
_audit_update_record             
;
2023-03-08 deposited with the CCDC.	2023-06-21 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            'C17 H19 N O2 S'
_chemical_formula_weight         301.39

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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

_cell_length_a                   14.4622(13)
_cell_length_b                   7.9861(9)
_cell_length_c                   27.635(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3191.7(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    5112
_cell_measurement_theta_min      2.5350
_cell_measurement_theta_max      27.8420

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_F_000             1280
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.030
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.207
_shelx_estimated_absorpt_T_min   0.994
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25609
_diffrn_reflns_av_unetI/netI     0.0543
_diffrn_reflns_av_R_equivalents  0.0781
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         2.038
_diffrn_reflns_theta_max         29.475
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.907
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.907
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.907
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4019
_reflns_number_gt                2554
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0446P)²+1.5431P] 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         4019
_refine_ls_number_parameters     230
_refine_ls_number_restraints     37
_refine_ls_R_factor_all          0.1215
_refine_ls_R_factor_gt           0.0730
_refine_ls_wR_factor_ref         0.1606
_refine_ls_wR_factor_gt          0.1413
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.084
_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 0.43308(5) 0.72367(10) 0.67074(2) 0.0553(2) Uani 1 1 d . . . . .
O2 O 0.72983(14) 0.6658(3) 0.56363(7) 0.0744(6) Uani 1 1 d D . . . .
O1 O 0.63038(15) 0.5779(4) 0.50826(7) 0.0932(8) Uani 1 1 d . . . . .
N1 N 0.36398(16) 0.8142(3) 0.76036(8) 0.0605(6) Uani 1 1 d . . . . .
C7 C 0.31753(17) 0.7090(3) 0.68527(9) 0.0480(6) Uani 1 1 d . . . . .
C6 C 0.29075(18) 0.7760(3) 0.73258(9) 0.0489(6) Uani 1 1 d . . . . .
C4 C 0.19981(19) 0.8052(3) 0.74773(9) 0.0534(7) Uani 1 1 d . . . . .
C10 C 0.41593(18) 0.6344(4) 0.61489(9) 0.0508(6) Uani 1 1 d . . . . .
C11 C 0.4895(2) 0.6120(4) 0.58039(9) 0.0550(7) Uani 1 1 d . . . . .
H11 H 0.473602 0.564408 0.550820 0.066 Uiso 1 1 calc R U . . .
C13 C 0.6452(2) 0.6278(4) 0.54834(10) 0.0618(8) Uani 1 1 d . . . . .
C9 C 0.3261(2) 0.5927(4) 0.60887(10) 0.0618(8) Uani 1 1 d . . . . .
H9 H 0.303489 0.541076 0.581122 0.074 Uiso 1 1 calc R U . . .
C8 C 0.27030(19) 0.6348(4) 0.64847(10) 0.0628(8) Uani 1 1 d . . . . .
H8 H 0.207057 0.613968 0.649526 0.075 Uiso 1 1 calc R U . . .
C12 C 0.5774(2) 0.6522(4) 0.58651(10) 0.0590(8) Uani 1 1 d . . . . .
H12 H 0.596243 0.697219 0.615933 0.071 Uiso 1 1 calc R U . . .
C3 C 0.1895(2) 0.8745(4) 0.79314(10) 0.0666(8) Uani 1 1 d . . . . .
H3 H 0.130253 0.896652 0.804587 0.080 Uiso 1 1 calc R U . . .
C5 C 0.11654(19) 0.7659(5) 0.71759(11) 0.0722(9) Uani 1 1 d . . . . .
H5A H 0.122605 0.818308 0.686485 0.108 Uiso 1 1 calc R U . . .
H5B H 0.062108 0.807431 0.733452 0.108 Uiso 1 1 calc R U . . .
H5C H 0.111514 0.646899 0.713517 0.108 Uiso 1 1 calc R U . . .
C1 C 0.3496(2) 0.8792(4) 0.80367(10) 0.0720(9) Uani 1 1 d . . . . .
H1 H 0.400545 0.904399 0.822885 0.086 Uiso 1 1 calc R U . . .
C2 C 0.2631(2) 0.9112(4) 0.82154(11) 0.0741(9) Uani 1 1 d . . . . .
H2 H 0.255174 0.956684 0.852238 0.089 Uiso 1 1 calc R U . . .
C14 C 0.8109(6) 0.626(3) 0.5351(4) 0.069(4) Uani 0.491(7) 1 d D . P A 1
H14A H 0.816428 0.701477 0.507870 0.082 Uiso 0.491(7) 1 calc R U P A 1
H14B H 0.807216 0.511890 0.523003 0.082 Uiso 0.491(7) 1 calc R U P A 1
C15 C 0.8932(5) 0.6450(12) 0.5691(3) 0.067(2) Uani 0.491(7) 1 d D . P A 1
H15A H 0.891727 0.754708 0.584075 0.080 Uiso 0.491(7) 1 calc R U P A 1
H15B H 0.890009 0.561199 0.594416 0.080 Uiso 0.491(7) 1 calc R U P A 1
C17 C 1.0651(6) 0.6276(16) 0.5727(3) 0.085(3) Uani 0.491(7) 1 d D . P A 1
H17A H 1.119391 0.628665 0.552699 0.127 Uiso 0.491(7) 1 calc R U P A 1
H17B H 1.065863 0.529936 0.592940 0.127 Uiso 0.491(7) 1 calc R U P A 1
H17C H 1.064233 0.726210 0.592577 0.127 Uiso 0.491(7) 1 calc R U P A 1
C16 C 0.9804(4) 0.6246(10) 0.5412(2) 0.076(2) Uani 0.491(7) 1 d D . P A 1
H16A H 0.984883 0.713838 0.517529 0.092 Uiso 0.491(7) 1 calc R U P A 1
H16B H 0.978409 0.519169 0.523853 0.092 Uiso 0.491(7) 1 calc R U P A 1
C15A C 0.8919(5) 0.7018(11) 0.5442(3) 0.079(2) Uani 0.509(7) 1 d D . P A 2
H15C H 0.935173 0.706506 0.517369 0.094 Uiso 0.509(7) 1 calc R U P A 2
H15D H 0.889916 0.812399 0.558609 0.094 Uiso 0.509(7) 1 calc R U P A 2
C16A C 0.9282(6) 0.5857(12) 0.5799(3) 0.086(3) Uani 0.509(7) 1 d D . P A 2
H16C H 0.927778 0.473771 0.566303 0.103 Uiso 0.509(7) 1 calc R U P A 2
H16D H 0.887306 0.585455 0.607785 0.103 Uiso 0.509(7) 1 calc R U P A 2
C17A C 1.0252(7) 0.6261(16) 0.5968(4) 0.108(4) Uani 0.509(7) 1 d D . P A 2
H17D H 1.067519 0.612697 0.570303 0.161 Uiso 0.509(7) 1 calc R U P A 2
H17E H 1.042168 0.551712 0.622567 0.161 Uiso 0.509(7) 1 calc R U P A 2
H17F H 1.027415 0.739665 0.608136 0.161 Uiso 0.509(7) 1 calc R U P A 2
C14A C 0.7983(6) 0.663(3) 0.5243(4) 0.076(4) Uani 0.509(7) 1 d D . P A 2
H14C H 0.781877 0.745750 0.499956 0.091 Uiso 0.509(7) 1 calc R U P A 2
H14D H 0.798837 0.553918 0.509038 0.091 Uiso 0.509(7) 1 calc R U P A 2


_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 C10 1.718(3) . ?
S1 C7 1.723(3) . ?
O2 C13 1.330(3) . ?
O2 C14 1.448(11) . ?
O2 C14A 1.471(11) . ?
O1 C13 1.196(3) . ?
N1 C1 1.321(3) . ?
N1 C6 1.343(3) . ?
C7 C8 1.361(4) . ?
C7 C6 1.465(4) . ?
C6 C4 1.400(3) . ?
C4 C3 1.380(4) . ?
C4 C5 1.497(4) . ?
C10 C9 1.352(4) . ?
C10 C11 1.440(4) . ?
C11 C12 1.321(4) . ?
C13 C12 1.454(4) . ?
C9 C8 1.400(4) . ?
C3 C2 1.356(4) . ?
C1 C2 1.368(4) . ?
C14 C15 1.522(11) . ?
C15 C16 1.487(9) . ?
C17 C16 1.502(9) . ?
C15A C16A 1.453(10) . ?
C15A C14A 1.493(11) . ?
C16A C17A 1.513(10) . ?

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
C10 S1 C7 92.35(13) . . ?
C13 O2 C14 121.5(6) . . ?
C13 O2 C14A 112.4(5) . . ?
C1 N1 C6 118.9(3) . . ?
C8 C7 C6 133.9(2) . . ?
C8 C7 S1 110.0(2) . . ?
C6 C7 S1 116.09(19) . . ?
N1 C6 C4 122.2(2) . . ?
N1 C6 C7 112.6(2) . . ?
C4 C6 C7 125.2(2) . . ?
C3 C4 C6 116.1(3) . . ?
C3 C4 C5 120.2(3) . . ?
C6 C4 C5 123.7(2) . . ?
C9 C10 C11 126.8(2) . . ?
C9 C10 S1 110.6(2) . . ?
C11 C10 S1 122.7(2) . . ?
C12 C11 C10 126.6(2) . . ?
O1 C13 O2 122.3(3) . . ?
O1 C13 C12 126.6(3) . . ?
O2 C13 C12 111.1(2) . . ?
C10 C9 C8 113.5(2) . . ?
C7 C8 C9 113.5(3) . . ?
C11 C12 C13 121.6(3) . . ?
C2 C3 C4 121.9(3) . . ?
N1 C1 C2 123.0(3) . . ?
C3 C2 C1 118.0(3) . . ?
O2 C14 C15 106.0(8) . . ?
C16 C15 C14 109.5(7) . . ?
C15 C16 C17 113.0(6) . . ?
C16A C15A C14A 116.5(9) . . ?
C15A C16A C17A 114.0(8) . . ?
O2 C14A C15A 109.6(9) . . ?

_refine_diff_density_max         0.187
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.041



