# Electronic Supplementary Material (ESI) for ChemComm.
# 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_2020_12_11_TM
_database_code_depnum_ccdc_archive 'CCDC 2110557'
loop_
_audit_author_name
_audit_author_address
'Shunsuke Moritani '
;Kyoto University
Japan
;
_audit_update_record             
;
2021-09-18 deposited with the CCDC.	2022-01-21 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C19 H17 N O3 S'
_chemical_formula_moiety         'C19 H17 N O3 S'
_chemical_formula_weight         339.41
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   6.478(2)
_cell_length_b                   8.078(3)
_cell_length_c                   15.574(5)
_cell_angle_alpha                81.981(8)
_cell_angle_beta                 89.271(9)
_cell_angle_gamma                88.832(8)
_cell_volume                     806.8(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2854
_cell_measurement_theta_min      3.00
_cell_measurement_theta_max      27.50
_cell_measurement_temperature    293
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             356.00
_exptl_absorpt_coefficient_mu    0.218
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.815
_exptl_absorpt_correction_T_max  0.957

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      293
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.111
_diffrn_reflns_number            6488
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_theta_max         27.480
_diffrn_reflns_theta_min         3.028
_diffrn_reflns_theta_full        27.480
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measured_fraction_theta_full 0.955
_diffrn_reflns_Laue_measured_fraction_max 0.000
_diffrn_reflns_Laue_measured_fraction_full 0.000
_diffrn_reflns_point_group_measured_fraction_max 0.000
_diffrn_reflns_point_group_measured_fraction_full 0.000
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       15
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3545
_reflns_number_gt                2917
_reflns_threshold_expression     F²>2.0σ(F²)

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0468
_refine_ls_wR_factor_ref         0.1554
_refine_ls_wR_factor_gt          0.1506
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3545
_refine_ls_number_parameters     217
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0966P)²+0.3480P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.67
_refine_diff_density_min         -0.72
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.22744(7) 0.26011(6) 0.16909(3) 0.01888(17) Uani 1 1 d . . .
O1 O 0.1549(2) 0.15088(19) 0.43405(9) 0.0262(3) Uani 1 1 d . . .
H1A H 0.1423 0.1683 0.3812 0.031 Uiso 1 1 calc R . .
O2 O 0.1065(2) 0.11781(17) 0.15886(9) 0.0255(3) Uani 1 1 d . . .
O3 O 0.4256(2) 0.27811(19) 0.12670(9) 0.0253(3) Uani 1 1 d . . .
N1 N 0.2536(3) 0.2563(2) 0.27554(10) 0.0203(4) Uani 1 1 d . . .
C1 C 0.4286(3) 0.3029(2) 0.30351(12) 0.0194(4) Uani 1 1 d . . .
H1 H 0.5284 0.3452 0.2634 0.023 Uiso 1 1 calc R . .
C2 C 0.4725(3) 0.2913(2) 0.39436(12) 0.0197(4) Uani 1 1 d . . .
C3 C 0.3341(3) 0.2100(2) 0.45574(12) 0.0204(4) Uani 1 1 d . . .
C4 C 0.3835(3) 0.1847(2) 0.54586(12) 0.0213(4) Uani 1 1 d . . .
C5 C 0.2457(4) 0.1027(3) 0.60853(13) 0.0266(5) Uani 1 1 d . . .
H5 H 0.1192 0.0666 0.5914 0.032 Uiso 1 1 calc R . .
C6 C 0.2987(4) 0.0766(3) 0.69436(14) 0.0303(5) Uani 1 1 d . . .
H6 H 0.2083 0.0226 0.7354 0.036 Uiso 1 1 calc R . .
C7 C 0.4901(4) 0.1317(3) 0.72028(14) 0.0323(5) Uani 1 1 d . . .
H7 H 0.5255 0.1133 0.7786 0.039 Uiso 1 1 calc R . .
C8 C 0.6247(4) 0.2120(3) 0.66079(14) 0.0304(5) Uani 1 1 d . . .
H8 H 0.7505 0.2474 0.6791 0.036 Uiso 1 1 calc R . .
C9 C 0.5746(3) 0.2419(3) 0.57148(12) 0.0236(4) Uani 1 1 d . . .
C10 C 0.7112(3) 0.3261(3) 0.50820(13) 0.0243(4) Uani 1 1 d . . .
H10 H 0.8357 0.3645 0.5260 0.029 Uiso 1 1 calc R . .
C11 C 0.6641(3) 0.3517(2) 0.42226(12) 0.0214(4) Uani 1 1 d . . .
C12 C 0.8088(3) 0.4449(3) 0.35687(13) 0.0266(5) Uani 1 1 d . . .
H12A H 0.9399 0.3871 0.3584 0.032 Uiso 1 1 calc R . .
H12B H 0.8271 0.5559 0.3707 0.032 Uiso 1 1 calc R . .
H12C H 0.7516 0.4512 0.2999 0.032 Uiso 1 1 calc R . .
C13 C 0.0771(3) 0.4419(2) 0.13891(11) 0.0186(4) Uani 1 1 d . . .
C14 C -0.1210(3) 0.4295(2) 0.10893(12) 0.0215(4) Uani 1 1 d . . .
H14 H -0.1774 0.3255 0.1062 0.026 Uiso 1 1 calc R . .
C15 C -0.2348(3) 0.5757(3) 0.08294(13) 0.0245(4) Uani 1 1 d . . .
H15 H -0.3679 0.5686 0.0622 0.029 Uiso 1 1 calc R . .
C16 C -0.1530(3) 0.7318(3) 0.08741(12) 0.0239(4) Uani 1 1 d . . .
C17 C 0.0470(4) 0.7399(3) 0.11904(14) 0.0286(5) Uani 1 1 d . . .
H17 H 0.1027 0.8437 0.1232 0.034 Uiso 1 1 calc R . .
C18 C 0.1631(3) 0.5967(3) 0.14423(14) 0.0251(4) Uani 1 1 d . . .
H18 H 0.2967 0.6034 0.1644 0.030 Uiso 1 1 calc R . .
C19 C -0.2761(4) 0.8891(3) 0.05786(14) 0.0329(5) Uani 1 1 d . . .
H19A H -0.4013 0.8895 0.0914 0.039 Uiso 1 1 calc R . .
H19B H -0.3090 0.8934 -0.0023 0.039 Uiso 1 1 calc R . .
H19C H -0.1963 0.9847 0.0657 0.039 Uiso 1 1 calc R . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b46 (Rigaku, 2016)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b46'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b46'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2'

#==============================================================================
# MOLECULAR GEOMETRY

_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 O2 1.4324(15) . ?
S1 O3 1.4369(16) . ?
S1 N1 1.6646(17) . ?
S1 C13 1.757(2) . ?
O1 C3 1.330(3) . ?
O1 H1A 0.8200 . ?
N1 C1 1.301(3) . ?
C1 C2 1.437(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.406(3) . ?
C2 C11 1.437(3) . ?
C3 C4 1.429(3) . ?
C4 C9 1.411(3) . ?
C4 C5 1.418(3) . ?
C5 C6 1.371(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.409(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.369(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.419(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.426(3) . ?
C10 C11 1.363(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.508(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.381(3) . ?
C13 C18 1.393(3) . ?
C14 C15 1.393(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.389(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.398(3) . ?
C16 C19 1.506(3) . ?
C17 C18 1.380(3) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 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
O2 S1 O3 118.87(9) . . ?
O2 S1 N1 105.74(9) . . ?
O3 S1 N1 110.04(9) . . ?
O2 S1 C13 108.56(9) . . ?
O3 S1 C13 109.33(9) . . ?
N1 S1 C13 103.13(8) . . ?
C3 O1 H1A 109.5 . . ?
C1 N1 S1 117.90(14) . . ?
N1 C1 C2 122.14(18) . . ?
N1 C1 H1 118.9 . . ?
C2 C1 H1 118.9 . . ?
C3 C2 C1 119.75(18) . . ?
C3 C2 C11 119.94(17) . . ?
C1 C2 C11 120.16(18) . . ?
O1 C3 C2 122.82(18) . . ?
O1 C3 C4 116.65(18) . . ?
C2 C3 C4 120.52(18) . . ?
C9 C4 C5 120.31(18) . . ?
C9 C4 C3 118.50(18) . . ?
C5 C4 C3 121.19(19) . . ?
C6 C5 C4 120.1(2) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C7 119.9(2) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C8 C7 C6 120.9(2) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C7 C8 C9 120.8(2) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C4 C9 C8 118.07(19) . . ?
C4 C9 C10 119.97(18) . . ?
C8 C9 C10 122.0(2) . . ?
C11 C10 C9 121.76(19) . . ?
C11 C10 H10 119.1 . . ?
C9 C10 H10 119.1 . . ?
C10 C11 C2 119.29(18) . . ?
C10 C11 C12 120.73(19) . . ?
C2 C11 C12 119.98(17) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C18 121.30(18) . . ?
C14 C13 S1 119.93(15) . . ?
C18 C13 S1 118.76(15) . . ?
C13 C14 C15 118.81(19) . . ?
C13 C14 H14 120.6 . . ?
C15 C14 H14 120.6 . . ?
C16 C15 C14 121.2(2) . . ?
C16 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C15 C16 C17 118.60(18) . . ?
C15 C16 C19 120.7(2) . . ?
C17 C16 C19 120.7(2) . . ?
C18 C17 C16 121.14(19) . . ?
C18 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?
C17 C18 C13 118.97(19) . . ?
C17 C18 H18 120.5 . . ?
C13 C18 H18 120.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

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
O2 S1 N1 C1 143.36(15) . . . . ?
O3 S1 N1 C1 13.81(17) . . . . ?
C13 S1 N1 C1 -102.73(16) . . . . ?
S1 N1 C1 C2 -174.84(14) . . . . ?
N1 C1 C2 C3 7.4(3) . . . . ?
N1 C1 C2 C11 -177.04(17) . . . . ?
C1 C2 C3 O1 -4.2(3) . . . . ?
C11 C2 C3 O1 -179.80(17) . . . . ?
C1 C2 C3 C4 174.68(17) . . . . ?
C11 C2 C3 C4 -0.9(3) . . . . ?
O1 C3 C4 C9 178.47(17) . . . . ?
C2 C3 C4 C9 -0.5(3) . . . . ?
O1 C3 C4 C5 -0.9(3) . . . . ?
C2 C3 C4 C5 -179.88(18) . . . . ?
C9 C4 C5 C6 -0.8(3) . . . . ?
C3 C4 C5 C6 178.52(19) . . . . ?
C4 C5 C6 C7 0.1(3) . . . . ?
C5 C6 C7 C8 0.2(3) . . . . ?
C6 C7 C8 C9 0.1(3) . . . . ?
C5 C4 C9 C8 1.1(3) . . . . ?
C3 C4 C9 C8 -178.25(18) . . . . ?
C5 C4 C9 C10 -179.22(18) . . . . ?
C3 C4 C9 C10 1.4(3) . . . . ?
C7 C8 C9 C4 -0.7(3) . . . . ?
C7 C8 C9 C10 179.6(2) . . . . ?
C4 C9 C10 C11 -0.9(3) . . . . ?
C8 C9 C10 C11 178.73(19) . . . . ?
C9 C10 C11 C2 -0.5(3) . . . . ?
C9 C10 C11 C12 178.46(18) . . . . ?
C3 C2 C11 C10 1.4(3) . . . . ?
C1 C2 C11 C10 -174.15(17) . . . . ?
C3 C2 C11 C12 -177.57(17) . . . . ?
C1 C2 C11 C12 6.9(3) . . . . ?
O2 S1 C13 C14 -1.74(18) . . . . ?
O3 S1 C13 C14 129.37(16) . . . . ?
N1 S1 C13 C14 -113.59(16) . . . . ?
O2 S1 C13 C18 179.55(15) . . . . ?
O3 S1 C13 C18 -49.34(18) . . . . ?
N1 S1 C13 C18 67.70(17) . . . . ?
C18 C13 C14 C15 0.6(3) . . . . ?
S1 C13 C14 C15 -178.07(14) . . . . ?
C13 C14 C15 C16 -0.5(3) . . . . ?
C14 C15 C16 C17 -0.3(3) . . . . ?
C14 C15 C16 C19 179.06(18) . . . . ?
C15 C16 C17 C18 1.0(3) . . . . ?
C19 C16 C17 C18 -178.34(19) . . . . ?
C16 C17 C18 C13 -0.9(3) . . . . ?
C14 C13 C18 C17 0.1(3) . . . . ?
S1 C13 C18 C17 178.79(16) . . . . ?

#==============================================================================
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O1 H1A N1 . . . 2.574(2) 0.820 1.843 147.6 no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
