# 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_sukexin_0116
_database_code_depnum_ccdc_archive 'CCDC 2067793'
_audit_update_record             
;
2021-03-03 deposited with the CCDC.	2021-06-02 downloaded from the CCDC.
;
_audit_creation_date             2020-04-20
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H15 N O2 S'
_chemical_formula_sum            'C17 H15 N O2 S'
_chemical_formula_weight         297.36
_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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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                   10.0441(4)
_cell_length_b                   18.6223(6)
_cell_length_c                   8.2831(4)
_cell_angle_alpha                90
_cell_angle_beta                 110.227(5)
_cell_angle_gamma                90
_cell_volume                     1453.76(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1913
_cell_measurement_temperature    293.78(10)
_cell_measurement_theta_max      68.9670
_cell_measurement_theta_min      8.5270
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.006
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84243
_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            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5264
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        66.576
_diffrn_reflns_theta_max         66.576
_diffrn_reflns_theta_min         4.692
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.78(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     57.00 125.00   1.00    1.50    --   54.00  38.00  30.00   68
  2  ω    103.00 177.00   1.00    2.00    --  108.00  38.00 -30.00   74
  3  ω    137.00 175.00   1.00    2.00    --  108.00 111.00 -90.00   38
  4  ω    101.00 173.00   1.00    2.00    --  108.00 111.00-120.00   72
  5  ω     85.00 177.00   1.00    2.00    --  108.00  38.00  60.00   92
  6  ω     87.00 136.00   1.00    2.00    --  108.00 -77.00 -90.00   49
  7  ω     86.00 111.00   1.00    2.00    --  108.00-111.00  30.00   25
  8  ω     82.00 108.00   1.00    2.00    --  108.00-111.00 150.00   26
  9  ω     44.00 107.00   1.00    2.00    --  108.00 -50.00 150.00   63
 10  ω     36.00  84.00   1.00    1.50    --   54.00  57.00 120.00   48
 11  ω    -33.00  18.00   1.00    1.00    --    0.00 -57.00  30.00   51
 12  ω     49.00 122.00   1.00    1.50    --   54.00  57.00-120.00   73
 13  ω      5.00  37.00   1.00    1.00    --    0.00  57.00-150.00   32
 14  ω     37.00  89.00   1.00    2.00    --  108.00-111.00 -30.00   52
 15  ω     26.00  89.00   1.00    1.50    --   54.00-125.00 -60.00   63
 16  ω     32.00  80.00   1.00    1.50    --   54.00-125.00-180.00   48
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0149922000
_diffrn_orient_matrix_UB_12      0.0804192000
_diffrn_orient_matrix_UB_13      -0.0339332000
_diffrn_orient_matrix_UB_21      -0.0008152000
_diffrn_orient_matrix_UB_22      0.0181293000
_diffrn_orient_matrix_UB_23      0.1810491000
_diffrn_orient_matrix_UB_31      0.1628263000
_diffrn_orient_matrix_UB_32      -0.0072837000
_diffrn_orient_matrix_UB_33      0.0728448000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2070
_reflns_number_total             2562
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.039
_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     192
_refine_ls_number_reflns         2562
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0419
_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)+(0.0572P)²+0.3084P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1087
_refine_ls_wR_factor_ref         0.1164
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C13(H13), C14(H14), C16(H16), C17(H17), C18(H18), C19(H19),
 C20(H20), C21(H21)
2.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.92711(7) 0.18940(3) 0.14189(8) 0.0593(2) Uani 1 1 d . . . . .
O2 O 0.62128(16) -0.03184(7) 0.3583(2) 0.0512(4) Uani 1 1 d . . . . .
N3 N 0.99788(17) 0.04851(9) 0.2168(2) 0.0425(4) Uani 1 1 d . . . . .
O4 O 0.77120(18) -0.11838(8) 0.3471(3) 0.0680(5) Uani 1 1 d . . . . .
C5 C 0.9016(2) 0.10342(11) 0.2083(3) 0.0440(5) Uani 1 1 d . . . . .
C6 C 0.7884(2) 0.07452(10) 0.2436(2) 0.0402(4) Uani 1 1 d . . . . .
C7 C 0.8160(2) -0.00024(10) 0.2771(2) 0.0391(4) Uani 1 1 d . . . . .
C8 C 0.6621(2) 0.11776(10) 0.2364(3) 0.0401(4) Uani 1 1 d . . . . .
C9 C 0.9475(2) -0.01498(11) 0.2610(2) 0.0410(4) Uani 1 1 d . . . . .
C10 C 1.0328(2) -0.07694(12) 0.2796(3) 0.0498(5) Uani 1 1 d . . . . .
H10 H 1.004955 -0.119978 0.315248 0.060 Uiso 1 1 calc R U . . .
C11 C 0.7371(2) -0.05546(10) 0.3298(3) 0.0426(5) Uani 1 1 d . . . . .
C12 C 0.5457(3) -0.08562(13) 0.4173(4) 0.0615(6) Uani 1 1 d . . . . .
H12A H 0.503000 -0.119297 0.326299 0.092 Uiso 1 1 calc R U . . .
H12B H 0.473213 -0.063031 0.450446 0.092 Uiso 1 1 calc R U . . .
H12C H 0.610632 -0.110382 0.514323 0.092 Uiso 1 1 calc R U . . .
C13 C 1.1216(2) 0.05157(13) 0.1813(3) 0.0522(5) Uani 1 1 d . . . . .
H13 H 1.151332 0.094770 0.148698 0.063 Uiso 1 1 calc R U . . .
C14 C 0.6763(3) 0.17521(12) 0.3478(3) 0.0528(5) Uani 1 1 d . . . . .
H14 H 0.763652 0.184175 0.432686 0.063 Uiso 1 1 calc R U . . .
C15 C 1.0693(3) 0.22417(13) 0.3260(4) 0.0662(7) Uani 1 1 d . . . . .
H15A H 1.115050 0.263217 0.290198 0.099 Uiso 1 1 calc R U . . .
H15B H 1.137148 0.186787 0.374702 0.099 Uiso 1 1 calc R U . . .
H15C H 1.031155 0.240941 0.410586 0.099 Uiso 1 1 calc R U . . .
C16 C 0.5303(2) 0.10566(12) 0.1112(3) 0.0502(5) Uani 1 1 d . . . . .
H16 H 0.518209 0.067135 0.036045 0.060 Uiso 1 1 calc R U . . .
C17 C 0.4165(2) 0.15053(14) 0.0972(3) 0.0593(6) Uani 1 1 d . . . . .
H17 H 0.328866 0.141966 0.012689 0.071 Uiso 1 1 calc R U . . .
C18 C 0.5620(3) 0.21931(13) 0.3339(4) 0.0633(7) Uani 1 1 d . . . . .
H18 H 0.572720 0.257176 0.410578 0.076 Uiso 1 1 calc R U . . .
C19 C 1.1556(2) -0.07355(13) 0.2454(3) 0.0580(6) Uani 1 1 d . . . . .
H19 H 1.210899 -0.114545 0.255991 0.070 Uiso 1 1 calc R U . . .
C20 C 1.1997(2) -0.00831(14) 0.1941(3) 0.0587(6) Uani 1 1 d . . . . .
H20 H 1.282928 -0.006593 0.168848 0.070 Uiso 1 1 calc R U . . .
C21 C 0.4328(3) 0.20760(14) 0.2079(4) 0.0642(7) Uani 1 1 d . . . . .
H21 H 0.356863 0.238030 0.197302 0.077 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 C5 1.741(2) . ?
S1 C15 1.811(3) . ?
O2 C11 1.339(3) . ?
O2 C12 1.440(3) . ?
N3 C5 1.392(3) . ?
N3 C9 1.384(3) . ?
N3 C13 1.374(3) . ?
O4 C11 1.215(2) . ?
C5 C6 1.378(3) . ?
C6 C7 1.428(3) . ?
C6 C8 1.486(3) . ?
C7 C9 1.400(3) . ?
C7 C11 1.455(3) . ?
C8 C14 1.388(3) . ?
C8 C16 1.389(3) . ?
C9 C10 1.413(3) . ?
C10 H10 0.9300 . ?
C10 C19 1.359(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13 0.9300 . ?
C13 C20 1.346(3) . ?
C14 H14 0.9300 . ?
C14 C18 1.384(3) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16 0.9300 . ?
C16 C17 1.388(3) . ?
C17 H17 0.9300 . ?
C17 C21 1.375(4) . ?
C18 H18 0.9300 . ?
C18 C21 1.373(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.408(4) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?

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
C5 S1 C15 102.83(11) . . ?
C11 O2 C12 115.03(17) . . ?
C9 N3 C5 109.26(17) . . ?
C13 N3 C5 128.52(19) . . ?
C13 N3 C9 122.16(18) . . ?
N3 C5 S1 121.07(15) . . ?
C6 C5 S1 130.45(16) . . ?
C6 C5 N3 108.19(17) . . ?
C5 C6 C7 107.64(18) . . ?
C5 C6 C8 122.38(17) . . ?
C7 C6 C8 129.93(18) . . ?
C6 C7 C11 131.18(18) . . ?
C9 C7 C6 107.39(17) . . ?
C9 C7 C11 121.32(17) . . ?
C14 C8 C6 120.05(18) . . ?
C14 C8 C16 118.30(19) . . ?
C16 C8 C6 121.47(19) . . ?
N3 C9 C7 107.50(17) . . ?
N3 C9 C10 117.60(19) . . ?
C7 C9 C10 134.9(2) . . ?
C9 C10 H10 120.0 . . ?
C19 C10 C9 119.9(2) . . ?
C19 C10 H10 120.0 . . ?
O2 C11 C7 114.67(17) . . ?
O4 C11 O2 121.5(2) . . ?
O4 C11 C7 123.8(2) . . ?
O2 C12 H12A 109.5 . . ?
O2 C12 H12B 109.5 . . ?
O2 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N3 C13 H13 120.2 . . ?
C20 C13 N3 119.6(2) . . ?
C20 C13 H13 120.2 . . ?
C8 C14 H14 119.7 . . ?
C18 C14 C8 120.7(2) . . ?
C18 C14 H14 119.7 . . ?
S1 C15 H15A 109.5 . . ?
S1 C15 H15B 109.5 . . ?
S1 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C8 C16 H16 119.7 . . ?
C17 C16 C8 120.6(2) . . ?
C17 C16 H16 119.7 . . ?
C16 C17 H17 119.8 . . ?
C21 C17 C16 120.3(2) . . ?
C21 C17 H17 119.8 . . ?
C14 C18 H18 119.7 . . ?
C21 C18 C14 120.5(2) . . ?
C21 C18 H18 119.7 . . ?
C10 C19 H19 119.8 . . ?
C10 C19 C20 120.4(2) . . ?
C20 C19 H19 119.8 . . ?
C13 C20 C19 120.2(2) . . ?
C13 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C17 C21 H21 120.2 . . ?
C18 C21 C17 119.5(2) . . ?
C18 C21 H21 120.2 . . ?

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 C5 C6 C7 174.52(16) . . . . ?
S1 C5 C6 C8 -3.0(3) . . . . ?
N3 C5 C6 C7 0.8(2) . . . . ?
N3 C5 C6 C8 -176.70(17) . . . . ?
N3 C9 C10 C19 -3.5(3) . . . . ?
N3 C13 C20 C19 -0.8(3) . . . . ?
C5 N3 C9 C7 1.3(2) . . . . ?
C5 N3 C9 C10 -178.65(18) . . . . ?
C5 N3 C13 C20 -178.7(2) . . . . ?
C5 C6 C7 C9 0.0(2) . . . . ?
C5 C6 C7 C11 176.2(2) . . . . ?
C5 C6 C8 C14 -63.1(3) . . . . ?
C5 C6 C8 C16 111.9(2) . . . . ?
C6 C7 C9 N3 -0.8(2) . . . . ?
C6 C7 C9 C10 179.1(2) . . . . ?
C6 C7 C11 O2 -2.9(3) . . . . ?
C6 C7 C11 O4 176.9(2) . . . . ?
C6 C8 C14 C18 175.0(2) . . . . ?
C6 C8 C16 C17 -174.4(2) . . . . ?
C7 C6 C8 C14 120.1(2) . . . . ?
C7 C6 C8 C16 -64.9(3) . . . . ?
C7 C9 C10 C19 176.6(2) . . . . ?
C8 C6 C7 C9 177.22(19) . . . . ?
C8 C6 C7 C11 -6.6(4) . . . . ?
C8 C14 C18 C21 -1.0(4) . . . . ?
C8 C16 C17 C21 -0.2(4) . . . . ?
C9 N3 C5 S1 -175.73(14) . . . . ?
C9 N3 C5 C6 -1.3(2) . . . . ?
C9 N3 C13 C20 -1.9(3) . . . . ?
C9 C7 C11 O2 172.87(17) . . . . ?
C9 C7 C11 O4 -7.4(3) . . . . ?
C9 C10 C19 C20 1.0(3) . . . . ?
C10 C19 C20 C13 1.2(4) . . . . ?
C11 C7 C9 N3 -177.41(17) . . . . ?
C11 C7 C9 C10 2.5(4) . . . . ?
C12 O2 C11 O4 2.6(3) . . . . ?
C12 O2 C11 C7 -177.62(18) . . . . ?
C13 N3 C5 S1 1.5(3) . . . . ?
C13 N3 C5 C6 175.91(19) . . . . ?
C13 N3 C9 C7 -176.13(17) . . . . ?
C13 N3 C9 C10 3.9(3) . . . . ?
C14 C8 C16 C17 0.7(3) . . . . ?
C14 C18 C21 C17 1.5(4) . . . . ?
C15 S1 C5 N3 -74.29(19) . . . . ?
C15 S1 C5 C6 112.7(2) . . . . ?
C16 C8 C14 C18 -0.1(3) . . . . ?
C16 C17 C21 C18 -0.9(4) . . . . ?

_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 1.203
_oxdiff_exptl_absorpt_empirical_full_min 0.806
