# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_ctw-1
_database_code_depnum_ccdc_archive 'CCDC 2116767'
loop_
_audit_author_name
_audit_author_address
CJW
;Southern Medical University
China
;
_audit_update_record             
;
2021-10-20 deposited with the CCDC.	2022-02-02 downloaded from the CCDC.
;
_audit_creation_date             2021-10-16
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.09.11 svn.r3730fd0d for OlexSys, GUI svn.r6159)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H17 N3 O2 S'
_chemical_formula_sum            'C14 H17 N3 O2 S'
_chemical_formula_weight         291.36
_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                   10.1981(7)
_cell_length_b                   13.4643(5)
_cell_length_c                   11.1726(8)
_cell_angle_alpha                90
_cell_angle_beta                 116.517(9)
_cell_angle_gamma                90
_cell_volume                     1372.74(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3925
_cell_measurement_temperature    179.99(10)
_cell_measurement_theta_max      29.3590
_cell_measurement_theta_min      2.2370
_shelx_estimated_absorpt_T_max   0.972
_shelx_estimated_absorpt_T_min   0.967
_exptl_absorpt_coefficient_mu    0.241
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63668
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0533
_diffrn_reflns_av_unetI/netI     0.0559
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6093
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.232
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      179.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -15.00  19.00   1.00    2.00    --   12.21  77.00 -90.00   34
  2  ω     62.00  88.00   1.00    2.00    --   12.21  77.00 -90.00   26
  3  ω    -20.00   7.00   1.00    2.00    --   12.21 -99.00-180.00   27
  4  ω     34.00  99.00   1.00    2.00    --   12.21-178.00 150.00   65
  5  ω     63.00  88.00   1.00    2.00    --   12.05  77.00-180.00   25
  6  ω     18.00  64.00   1.00    2.00    --   12.05  77.00 -90.00   46
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0236761000
_diffrn_orient_matrix_UB_12      0.0501821000
_diffrn_orient_matrix_UB_13      0.0090368000
_diffrn_orient_matrix_UB_21      -0.0707032000
_diffrn_orient_matrix_UB_22      0.0154823000
_diffrn_orient_matrix_UB_23      -0.0100517000
_diffrn_orient_matrix_UB_31      0.0220521000
_diffrn_orient_matrix_UB_32      -0.0042487000
_diffrn_orient_matrix_UB_33      0.0696017000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2055
_reflns_number_total             2396
_reflns_odcompleteness_completeness 99.22
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       0.028(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2396
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0556
_refine_ls_R_factor_gt           0.0477
_refine_ls_restrained_S_all      1.068
_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)+(0.0713P)²+0.4678P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1263
_refine_ls_wR_factor_ref         0.1336
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Rotating group:
 N3(H3A,H3B)
2.b Ternary CH refined with riding coordinates:
 C12(H12)
2.c Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C13(H13A,H13B), C14(H14A,H14B)
2.d Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6)
2.e Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   mixed
_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 0.43602(6) 0.22751(4) 0.87636(5) 0.0220(2) Uani 1 1 d . . . . .
O1 O 0.45105(19) 0.24578(12) 0.75575(16) 0.0304(5) Uani 1 1 d . . . . .
O2 O 0.52791(18) 0.15249(12) 0.96732(16) 0.0317(5) Uani 1 1 d . . . . .
N1 N 0.2432(2) 0.54123(14) 0.74778(19) 0.0253(5) Uani 1 1 d . . . . .
N2 N 0.1711(2) 0.53011(14) 0.82639(19) 0.0263(5) Uani 1 1 d . . . . .
N3 N 0.4535(2) 0.47871(15) 0.7275(2) 0.0285(5) Uani 1 1 d . . . . .
H3A H 0.466166 0.419282 0.706274 0.034 Uiso 1 1 d R U . . .
H3B H 0.417919 0.515194 0.656837 0.034 Uiso 1 1 d R U . . .
C1 C 0.1968(3) 0.61689(16) 0.6476(2) 0.0239(5) Uani 1 1 d . . . . .
C2 C 0.2154(3) 0.71558(17) 0.6860(3) 0.0294(6) Uani 1 1 d . . . . .
H2 H 0.258769 0.732923 0.776033 0.035 Uiso 1 1 calc R U . . .
C3 C 0.1684(3) 0.78774(18) 0.5881(3) 0.0362(7) Uani 1 1 d . . . . .
H3 H 0.179623 0.854373 0.612617 0.043 Uiso 1 1 calc R U . . .
C4 C 0.1051(3) 0.7626(2) 0.4549(3) 0.0373(7) Uani 1 1 d . . . . .
H4 H 0.074396 0.811975 0.389821 0.045 Uiso 1 1 calc R U . . .
C5 C 0.0875(3) 0.6639(2) 0.4181(3) 0.0362(6) Uani 1 1 d . . . . .
H5 H 0.044668 0.646749 0.328007 0.043 Uiso 1 1 calc R U . . .
C6 C 0.1330(3) 0.59050(18) 0.5143(2) 0.0288(6) Uani 1 1 d . . . . .
H6 H 0.120915 0.523917 0.489542 0.035 Uiso 1 1 calc R U . . .
C7 C 0.3566(2) 0.47679(16) 0.7829(2) 0.0218(5) Uani 1 1 d . . . . .
C8 C 0.3581(2) 0.42042(16) 0.8870(2) 0.0211(5) Uani 1 1 d . . . . .
C9 C 0.2413(2) 0.45633(16) 0.9088(2) 0.0222(5) Uani 1 1 d . . . . .
C10 C 0.1959(3) 0.42412(18) 1.0126(2) 0.0314(6) Uani 1 1 d . . . . .
H10A H 0.117952 0.465998 1.008867 0.047 Uiso 1 1 calc R U . . .
H10B H 0.277892 0.429140 1.099545 0.047 Uiso 1 1 calc R U . . .
H10C H 0.162649 0.356519 0.996285 0.047 Uiso 1 1 calc R U . . .
C11 C 0.4668(3) 0.34262(16) 0.9643(2) 0.0229(5) Uani 1 1 d . . . . .
H11A H 0.462508 0.331541 1.048294 0.028 Uiso 1 1 calc R U . . .
H11B H 0.564442 0.366315 0.984979 0.028 Uiso 1 1 calc R U . . .
C12 C 0.2529(3) 0.19733(17) 0.8287(2) 0.0255(6) Uani 1 1 d . . . . .
H12 H 0.179862 0.234929 0.753293 0.031 Uiso 1 1 calc R U . . .
C13 C 0.2071(3) 0.16367(18) 0.9328(3) 0.0325(6) Uani 1 1 d . . . . .
H13A H 0.281540 0.161391 1.025023 0.039 Uiso 1 1 calc R U . . .
H13B H 0.110166 0.182389 0.920882 0.039 Uiso 1 1 calc R U . . .
C14 C 0.2170(3) 0.09012(18) 0.8383(2) 0.0318(6) Uani 1 1 d . . . . .
H14A H 0.126187 0.064109 0.768859 0.038 Uiso 1 1 calc R U . . .
H14B H 0.297568 0.043111 0.873005 0.038 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 O1 1.4437(17) . ?
S1 O2 1.4425(16) . ?
S1 C11 1.786(2) . ?
S1 C12 1.746(2) . ?
N1 N2 1.382(3) . ?
N1 C1 1.429(3) . ?
N1 C7 1.356(3) . ?
N2 C9 1.326(3) . ?
N3 H3A 0.8606 . ?
N3 H3B 0.8609 . ?
N3 C7 1.380(3) . ?
C1 C2 1.383(3) . ?
C1 C6 1.379(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.379(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.374(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.379(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.379(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.383(3) . ?
C8 C9 1.404(3) . ?
C8 C11 1.489(3) . ?
C9 C10 1.492(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12 0.9800 . ?
C12 C13 1.504(3) . ?
C12 C14 1.505(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.484(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?

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
O1 S1 C11 107.45(10) . . ?
O1 S1 C12 107.44(11) . . ?
O2 S1 O1 118.07(11) . . ?
O2 S1 C11 108.69(10) . . ?
O2 S1 C12 108.78(11) . . ?
C12 S1 C11 105.74(11) . . ?
N2 N1 C1 119.41(18) . . ?
C7 N1 N2 111.94(18) . . ?
C7 N1 C1 128.6(2) . . ?
C9 N2 N1 104.34(18) . . ?
H3A N3 H3B 109.3 . . ?
C7 N3 H3A 109.4 . . ?
C7 N3 H3B 109.2 . . ?
C2 C1 N1 119.4(2) . . ?
C6 C1 N1 119.6(2) . . ?
C6 C1 C2 121.0(2) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 C1 118.7(2) . . ?
C3 C2 H2 120.7 . . ?
C2 C3 H3 119.5 . . ?
C4 C3 C2 121.0(2) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 120.1 . . ?
C3 C4 C5 119.7(2) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 119.8 . . ?
C6 C5 C4 120.3(2) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 H6 120.4 . . ?
C5 C6 C1 119.3(2) . . ?
C5 C6 H6 120.4 . . ?
N1 C7 N3 123.2(2) . . ?
N1 C7 C8 106.4(2) . . ?
N3 C7 C8 130.2(2) . . ?
C7 C8 C9 105.4(2) . . ?
C7 C8 C11 126.9(2) . . ?
C9 C8 C11 127.7(2) . . ?
N2 C9 C8 111.9(2) . . ?
N2 C9 C10 119.9(2) . . ?
C8 C9 C10 128.1(2) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
S1 C11 H11A 109.0 . . ?
S1 C11 H11B 109.0 . . ?
C8 C11 S1 112.86(15) . . ?
C8 C11 H11A 109.0 . . ?
C8 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
S1 C12 H12 116.2 . . ?
C13 C12 S1 119.57(17) . . ?
C13 C12 H12 116.2 . . ?
C13 C12 C14 59.11(16) . . ?
C14 C12 S1 117.54(18) . . ?
C14 C12 H12 116.2 . . ?
C12 C13 H13A 117.7 . . ?
C12 C13 H13B 117.7 . . ?
H13A C13 H13B 114.8 . . ?
C14 C13 C12 60.48(16) . . ?
C14 C13 H13A 117.7 . . ?
C14 C13 H13B 117.7 . . ?
C12 C14 H14A 117.7 . . ?
C12 C14 H14B 117.7 . . ?
C13 C14 C12 60.41(16) . . ?
C13 C14 H14A 117.7 . . ?
C13 C14 H14B 117.7 . . ?
H14A C14 H14B 114.9 . . ?

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 C12 C13 C14 -106.3(2) . . . . ?
S1 C12 C14 C13 109.7(2) . . . . ?
O1 S1 C11 C8 61.75(19) . . . . ?
O1 S1 C12 C13 173.49(18) . . . . ?
O1 S1 C12 C14 105.19(19) . . . . ?
O2 S1 C11 C8 -169.42(16) . . . . ?
O2 S1 C12 C13 44.6(2) . . . . ?
O2 S1 C12 C14 -23.7(2) . . . . ?
N1 N2 C9 C8 0.9(2) . . . . ?
N1 N2 C9 C10 178.5(2) . . . . ?
N1 C1 C2 C3 -179.2(2) . . . . ?
N1 C1 C6 C5 179.5(2) . . . . ?
N1 C7 C8 C9 -0.2(2) . . . . ?
N1 C7 C8 C11 -176.8(2) . . . . ?
N2 N1 C1 C2 67.1(3) . . . . ?
N2 N1 C1 C6 -112.3(2) . . . . ?
N2 N1 C7 N3 -174.2(2) . . . . ?
N2 N1 C7 C8 0.8(2) . . . . ?
N3 C7 C8 C9 174.3(2) . . . . ?
N3 C7 C8 C11 -2.3(4) . . . . ?
C1 N1 N2 C9 -178.96(19) . . . . ?
C1 N1 C7 N3 3.5(4) . . . . ?
C1 N1 C7 C8 178.5(2) . . . . ?
C1 C2 C3 C4 -0.5(4) . . . . ?
C2 C1 C6 C5 0.1(4) . . . . ?
C2 C3 C4 C5 0.4(4) . . . . ?
C3 C4 C5 C6 0.0(4) . . . . ?
C4 C5 C6 C1 -0.2(4) . . . . ?
C6 C1 C2 C3 0.2(4) . . . . ?
C7 N1 N2 C9 -1.0(2) . . . . ?
C7 N1 C1 C2 -110.4(3) . . . . ?
C7 N1 C1 C6 70.1(3) . . . . ?
C7 C8 C9 N2 -0.5(3) . . . . ?
C7 C8 C9 C10 -177.9(2) . . . . ?
C7 C8 C11 S1 -78.0(3) . . . . ?
C9 C8 C11 S1 106.1(2) . . . . ?
C11 S1 C12 C13 -72.0(2) . . . . ?
C11 S1 C12 C14 -140.29(18) . . . . ?
C11 C8 C9 N2 176.1(2) . . . . ?
C11 C8 C9 C10 -1.3(4) . . . . ?
C12 S1 C11 C8 -52.77(19) . . . . ?

_olex2_date_sample_data_collection 2021-10-15
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 5.420
_oxdiff_exptl_absorpt_empirical_full_min 0.636
