# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 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_3
_database_code_depnum_ccdc_archive 'CCDC 2064800'
loop_
_audit_author_name
_audit_author_address
'Hao Su'
;Beijing Institute of Technology
China
;
_audit_update_record             
;
2021-02-24 deposited with the CCDC.	2021-05-18 downloaded from the CCDC.
;
_audit_creation_date             2020-09-18
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        TL7B
_chemical_formula_moiety         'C16 H18 N2 O2 S'
_chemical_formula_sum            'C16 H18 N2 O2 S'
_chemical_formula_weight         302.38
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   19.277(4)
_cell_length_b                   9.640(2)
_cell_length_c                   8.8871(18)
_cell_angle_alpha                90
_cell_angle_beta                 81.711(7)
_cell_angle_gamma                90
_cell_volume                     1634.2(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2614
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      21.038
_cell_measurement_theta_min      2.364
_shelx_estimated_absorpt_T_max   0.980
_shelx_estimated_absorpt_T_min   0.941
_exptl_absorpt_coefficient_mu    0.204
_exptl_absorpt_correction_T_max  0.7449
_exptl_absorpt_correction_T_min  0.6917
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1209 before and 0.0398 after correction.
The Ratio of minimum to maximum transmission is 0.9286.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0377
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_Laue_measured_fraction_full 0.773
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            12926
_diffrn_reflns_point_group_measured_fraction_full 0.773
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         23.092
_diffrn_reflns_theta_min         2.135
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.773
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           35.0
_diffrn_source_power             1.575
_diffrn_source_voltage           45.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1654
_reflns_number_total             2295
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2013/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.385
_refine_diff_density_min         -0.405
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         2295
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0824
_refine_ls_R_factor_gt           0.0567
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0889P)²+1.2810P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1576
_refine_ls_wR_factor_ref         0.1782
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C2(H2A), C3(H3), C6(H6), C8(H8), C9(H9), C10(H10)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.57338(6) 0.96192(12) 0.32435(14) 0.0810(5) Uani 1 1 d . . . . .
O1 O 0.43375(13) 0.8620(3) 0.2562(3) 0.0632(7) Uani 1 1 d . . . . .
O2 O 0.24627(12) 0.6769(3) 0.2724(3) 0.0607(7) Uani 1 1 d . . . . .
H2 H 0.2830 0.7035 0.2993 0.091 Uiso 1 1 calc R U . . .
N1 N 0.41487(14) 0.7188(3) 0.4604(3) 0.0542(8) Uani 1 1 d . . . . .
H1 H 0.4304 0.6871 0.5396 0.065 Uiso 1 1 calc R U . . .
N2 N 0.34938(14) 0.6830(3) 0.4315(3) 0.0525(8) Uani 1 1 d . . . . .
C1 C 0.6423(2) 0.9168(6) 0.4036(5) 0.0841(14) Uani 1 1 d . . . . .
H1A H 0.6834 0.9687 0.3938 0.101 Uiso 1 1 calc R U . . .
C2 C 0.6337(2) 0.7987(6) 0.4833(6) 0.0932(15) Uani 1 1 d . . . . .
H2A H 0.6682 0.7628 0.5354 0.112 Uiso 1 1 calc R U . . .
C3 C 0.56774(16) 0.7322(4) 0.4823(4) 0.0522(9) Uani 1 1 d . . . . .
H3 H 0.5534 0.6478 0.5271 0.063 Uiso 1 1 calc R U . . .
C4 C 0.52722(18) 0.8230(4) 0.3969(4) 0.0529(9) Uani 1 1 d . . . . .
C5 C 0.45500(18) 0.8047(4) 0.3635(4) 0.0504(9) Uani 1 1 d . . . . .
C6 C 0.31417(18) 0.5990(4) 0.5250(4) 0.0561(9) Uani 1 1 d . . . . .
H6 H 0.3328 0.5711 0.6110 0.067 Uiso 1 1 calc R U . . .
C7 C 0.24660(17) 0.5465(3) 0.5011(4) 0.0515(9) Uani 1 1 d . . . . .
C8 C 0.2127(2) 0.4528(4) 0.6059(5) 0.0699(11) Uani 1 1 d . . . . .
H8 H 0.2331 0.4279 0.6907 0.084 Uiso 1 1 calc R U . . .
C9 C 0.1493(2) 0.3970(5) 0.5847(6) 0.0828(13) Uani 1 1 d . . . . .
H9 H 0.1263 0.3353 0.6554 0.099 Uiso 1 1 calc R U . . .
C10 C 0.1198(2) 0.4334(4) 0.4577(6) 0.0740(12) Uani 1 1 d . . . . .
H10 H 0.0773 0.3930 0.4442 0.089 Uiso 1 1 calc R U . . .
C11 C 0.21469(16) 0.5838(3) 0.3747(4) 0.0496(9) Uani 1 1 d . . . . .
C12 C 0.15002(17) 0.5264(4) 0.3495(4) 0.0555(10) Uani 1 1 d . . . . .
C13 C 0.11517(18) 0.5669(4) 0.2114(5) 0.0655(11) Uani 1 1 d . . . . .
C14 C 0.1637(2) 0.5357(5) 0.0623(5) 0.0800(13) Uani 1 1 d . . . . .
H14A H 0.2051 0.5918 0.0566 0.120 Uiso 1 1 calc R U . . .
H14B H 0.1396 0.5565 -0.0224 0.120 Uiso 1 1 calc R U . . .
H14C H 0.1765 0.4394 0.0595 0.120 Uiso 1 1 calc R U . . .
C15 C 0.0970(2) 0.7230(4) 0.2189(6) 0.0819(13) Uani 1 1 d . . . . .
H15A H 0.0664 0.7423 0.3117 0.123 Uiso 1 1 calc R U . . .
H15B H 0.0740 0.7474 0.1337 0.123 Uiso 1 1 calc R U . . .
H15C H 0.1392 0.7762 0.2159 0.123 Uiso 1 1 calc R U . . .
C16 C 0.0467(2) 0.4872(5) 0.2071(6) 0.0943(16) Uani 1 1 d . . . . .
H16A H 0.0561 0.3894 0.2035 0.141 Uiso 1 1 calc R U . . .
H16B H 0.0268 0.5140 0.1185 0.141 Uiso 1 1 calc R U . . .
H16C H 0.0143 0.5082 0.2967 0.141 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 C1 1.649(5) . ?
S1 C4 1.683(4) . ?
O1 C5 1.223(4) . ?
O2 H2 0.8200 . ?
O2 C11 1.358(4) . ?
N1 H1 0.8600 . ?
N1 N2 1.369(4) . ?
N1 C5 1.354(4) . ?
N2 C6 1.282(4) . ?
C1 H1A 0.9300 . ?
C1 C2 1.338(6) . ?
C2 H2A 0.9300 . ?
C2 C3 1.426(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.458(5) . ?
C4 C5 1.475(5) . ?
C6 H6 0.9300 . ?
C6 C7 1.441(5) . ?
C7 C8 1.390(5) . ?
C7 C11 1.404(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.374(6) . ?
C9 H9 0.9300 . ?
C9 C10 1.379(6) . ?
C10 H10 0.9300 . ?
C10 C12 1.381(5) . ?
C11 C12 1.411(5) . ?
C12 C13 1.532(6) . ?
C13 C14 1.537(6) . ?
C13 C15 1.544(5) . ?
C13 C16 1.532(5) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 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
C1 S1 C4 92.3(2) . . ?
C11 O2 H2 109.5 . . ?
N2 N1 H1 120.2 . . ?
C5 N1 H1 120.2 . . ?
C5 N1 N2 119.5(3) . . ?
C6 N2 N1 117.0(3) . . ?
S1 C1 H1A 123.0 . . ?
C2 C1 S1 113.9(3) . . ?
C2 C1 H1A 123.0 . . ?
C1 C2 H2A 122.6 . . ?
C1 C2 C3 114.9(4) . . ?
C3 C2 H2A 122.6 . . ?
C2 C3 H3 126.9 . . ?
C2 C3 C4 106.2(3) . . ?
C4 C3 H3 126.9 . . ?
C3 C4 S1 112.6(2) . . ?
C3 C4 C5 128.6(3) . . ?
C5 C4 S1 118.7(3) . . ?
O1 C5 N1 123.2(3) . . ?
O1 C5 C4 122.3(3) . . ?
N1 C5 C4 114.5(3) . . ?
N2 C6 H6 118.9 . . ?
N2 C6 C7 122.1(3) . . ?
C7 C6 H6 118.9 . . ?
C8 C7 C6 118.5(3) . . ?
C8 C7 C11 119.0(3) . . ?
C11 C7 C6 122.5(3) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 C7 120.3(4) . . ?
C9 C8 H8 119.9 . . ?
C8 C9 H9 120.3 . . ?
C8 C9 C10 119.5(4) . . ?
C10 C9 H9 120.3 . . ?
C9 C10 H10 118.2 . . ?
C9 C10 C12 123.6(4) . . ?
C12 C10 H10 118.2 . . ?
O2 C11 C7 120.0(3) . . ?
O2 C11 C12 118.3(3) . . ?
C7 C11 C12 121.7(3) . . ?
C10 C12 C11 116.0(4) . . ?
C10 C12 C13 122.3(3) . . ?
C11 C12 C13 121.8(3) . . ?
C12 C13 C14 111.0(3) . . ?
C12 C13 C15 109.7(3) . . ?
C12 C13 C16 111.8(3) . . ?
C14 C13 C15 109.5(4) . . ?
C16 C13 C14 107.4(3) . . ?
C16 C13 C15 107.4(3) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 N2 0.82 1.87 2.601(3) 148.1 .
N1 H1 O1 0.86 1.99 2.815(4) 159.9 4_576

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
S1 C1 C2 C3 1.4(6) . . . . ?
S1 C4 C5 O1 19.9(5) . . . . ?
S1 C4 C5 N1 -160.5(2) . . . . ?
O2 C11 C12 C10 -179.4(3) . . . . ?
O2 C11 C12 C13 -0.2(5) . . . . ?
N1 N2 C6 C7 -175.8(3) . . . . ?
N2 N1 C5 O1 6.2(5) . . . . ?
N2 N1 C5 C4 -173.4(3) . . . . ?
N2 C6 C7 C8 178.3(3) . . . . ?
N2 C6 C7 C11 -0.2(6) . . . . ?
C1 S1 C4 C3 -2.6(3) . . . . ?
C1 S1 C4 C5 179.7(3) . . . . ?
C1 C2 C3 C4 -3.2(5) . . . . ?
C2 C3 C4 S1 3.6(4) . . . . ?
C2 C3 C4 C5 -179.0(4) . . . . ?
C3 C4 C5 O1 -157.3(3) . . . . ?
C3 C4 C5 N1 22.3(5) . . . . ?
C4 S1 C1 C2 0.7(4) . . . . ?
C5 N1 N2 C6 178.5(3) . . . . ?
C6 C7 C8 C9 -178.0(4) . . . . ?
C6 C7 C11 O2 -2.7(5) . . . . ?
C6 C7 C11 C12 177.0(3) . . . . ?
C7 C8 C9 C10 0.8(7) . . . . ?
C7 C11 C12 C10 0.9(5) . . . . ?
C7 C11 C12 C13 -179.9(3) . . . . ?
C8 C7 C11 O2 178.9(3) . . . . ?
C8 C7 C11 C12 -1.5(5) . . . . ?
C8 C9 C10 C12 -1.4(7) . . . . ?
C9 C10 C12 C11 0.5(6) . . . . ?
C9 C10 C12 C13 -178.7(4) . . . . ?
C10 C12 C13 C14 -122.6(4) . . . . ?
C10 C12 C13 C15 116.3(4) . . . . ?
C10 C12 C13 C16 -2.6(5) . . . . ?
C11 C7 C8 C9 0.6(6) . . . . ?
C11 C12 C13 C14 58.3(5) . . . . ?
C11 C12 C13 C15 -62.8(4) . . . . ?
C11 C12 C13 C16 178.3(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
