# 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_iw2201
_database_code_depnum_ccdc_archive 'CCDC 2143554'
loop_
_audit_author_name
_audit_author_address
'Ikuhide Fujisawa'
;Toyohashi University of Technology
Japan
;
_audit_update_record             
;
2022-01-21 deposited with the CCDC.	2022-10-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C15 H15 N O S'
_chemical_formula_sum            'C15 H15 N O S'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane/Hexane'
_chemical_melting_point          ?


_exptl_crystal_description       Platelet

_exptl_crystal_colour            Colorless
_diffrn_ambient_temperature      120
_chemical_formula_weight         257.34

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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'
_chemical_absolute_configuration ad

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_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.
;

_cell_length_a                   6.4659(14)
_cell_length_b                   7.0218(15)
_cell_length_c                   14.113(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.163(4)
_cell_angle_gamma                90
_cell_volume                     639.1(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    120

_cell_measurement_reflns_used    6365

_cell_measurement_theta_min      2.9

_cell_measurement_theta_max      30.0

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_F_000             272
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.35

_exptl_crystal_size_mid          0.30

_exptl_crystal_size_min          0.03

_exptl_absorpt_coefficient_mu    0.240
_shelx_estimated_absorpt_T_min   0.921
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   Numerical

_exptl_absorpt_correction_T_min  0.876

_exptl_absorpt_correction_T_max  0.972

_exptl_absorpt_process_details   'NUMABS (Rigaku Corp.)'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'Rotating Anode'
_diffrn_measurement_device_type  
;
AFC7R, 4-circle diffractometer with Mercury CCD camera (Rigaku Corp.)
;

_diffrn_measurement_method       
;
Oscillation method with Fine-Slice process
profile data from φ-scans
;
_diffrn_detector_area_resol_mean 14.7059

_diffrn_reflns_number            12012
_diffrn_reflns_av_unetI/netI     0.0409
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.894
_diffrn_reflns_theta_max         32.033
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4426
_reflns_number_gt                4097
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.858
_reflns_Friedel_fraction_max     0.987
_reflns_Friedel_fraction_full    0.992

_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       
;
Rigaku CrystalClear-SM Expert 2.0 r16
;
_computing_cell_refinement       
;
Rigaku CrystalClear-SM Expert 2.0 r16
;
_computing_data_reduction        
;
Rigaku CrystalClear-SM Expert 2.0 r16
;
_computing_structure_solution    'SHELXT-2014/5 (G.M. Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (G.M. Sheldrick, 2018)'
_computing_molecular_graphics    'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'
_computing_publication_material  
;Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)
;

_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)+(0.0460P)²+0.0863P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall

_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1733 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(2)

_refine_ls_number_reflns         4426
_refine_ls_number_parameters     223
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0399
_refine_ls_wR_factor_ref         0.0977
_refine_ls_wR_factor_gt          0.0943
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_refine_ls_shift/su_max          0.000
_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 0.80839(7) 0.59767(8) 0.41996(3) 0.02130(11) Uani 1 1 d . . . . .
C1 C 0.9159(3) 0.6021(3) 0.53132(11) 0.0171(3) Uani 1 1 d . . . . .
N1 N 1.1177(2) 0.5973(3) 0.55762(10) 0.0192(3) Uani 1 1 d . . . . .
C2 C 1.1688(3) 0.6274(3) 0.65936(14) 0.0218(4) Uani 1 1 d . . . . .
H1 H 1.254(5) 0.515(5) 0.684(2) 0.033(8) Uiso 1 1 d . . . . .
H2 H 1.254(4) 0.753(4) 0.6702(18) 0.018(6) Uiso 1 1 d . . . . .
C3 C 0.9599(3) 0.6403(3) 0.70115(14) 0.0201(4) Uani 1 1 d . . . . .
C4 C 0.7986(3) 0.6186(3) 0.61721(12) 0.0186(3) Uani 1 1 d . . . . .
H3 H 0.666(5) 0.691(4) 0.617(2) 0.024(7) Uiso 1 1 d . . . . .
C5 C 0.8298(3) 0.4611(3) 0.69163(14) 0.0192(4) Uani 1 1 d . . . . .
H4 H 0.896(4) 0.343(4) 0.6690(18) 0.018(6) Uiso 1 1 d . . . . .
C6 C 0.6687(3) 0.4355(3) 0.76016(13) 0.0193(4) Uani 1 1 d . . . . .
C7 C 0.5582(3) 0.2660(3) 0.76326(15) 0.0219(4) Uani 1 1 d . . . . .
H5 H 0.591(5) 0.163(4) 0.723(2) 0.030(8) Uiso 1 1 d . . . . .
C8 C 0.3988(4) 0.2429(3) 0.82363(15) 0.0240(4) Uani 1 1 d . . . . .
H6 H 0.326(5) 0.115(6) 0.824(2) 0.045(9) Uiso 1 1 d . . . . .
C9 C 0.3502(3) 0.3924(3) 0.88306(14) 0.0239(4) Uani 1 1 d . . . . .
C10 C 0.4657(4) 0.5594(3) 0.88436(15) 0.0248(4) Uani 1 1 d . . . . .
H7 H 0.440(5) 0.658(5) 0.930(2) 0.038(9) Uiso 1 1 d . . . . .
C11 C 0.6261(3) 0.5838(4) 0.82379(12) 0.0211(3) Uani 1 1 d . . . . .
C12 C 0.7573(4) 0.7529(3) 0.83053(15) 0.0250(4) Uani 1 1 d . . . . .
H8 H 0.733(5) 0.849(5) 0.876(2) 0.035(8) Uiso 1 1 d . . . . .
C13 C 0.9194(4) 0.7749(3) 0.77705(15) 0.0236(4) Uani 1 1 d . . . . .
H9 H 1.004(5) 0.889(5) 0.784(2) 0.030(7) Uiso 1 1 d . . . . .
C14 C 1.2832(3) 0.5796(4) 0.49444(15) 0.0238(4) Uani 1 1 d . . . . .
H10 H 1.381(6) 0.495(5) 0.524(2) 0.037(9) Uiso 1 1 d . . . . .
H11 H 1.227(5) 0.541(5) 0.429(2) 0.033(8) Uiso 1 1 d . . . . .
H12 H 1.355(5) 0.710(6) 0.490(2) 0.034(8) Uiso 1 1 d . . . . .
O1 O 0.1922(3) 0.3879(3) 0.94258(12) 0.0309(4) Uani 1 1 d . . . . .
C15 C 0.0590(4) 0.2254(4) 0.93748(19) 0.0340(5) Uani 1 1 d . . . . .
H13 H -0.043(5) 0.248(5) 0.985(2) 0.033(8) Uiso 1 1 d . . . . .
H15 H 0.147(5) 0.104(7) 0.959(2) 0.053(10) Uiso 1 1 d . . . . .
H14 H -0.008(5) 0.214(6) 0.872(2) 0.046(9) Uiso 1 1 d . . . . .


_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 1.6720(17) . ?
C1 N1 1.331(2) . ?
C1 C4 1.480(2) . ?
N1 C14 1.447(2) . ?
N1 C2 1.465(2) . ?
C2 C3 1.516(3) . ?
C2 H1 1.01(3) . ?
C2 H2 1.04(3) . ?
C3 C13 1.466(3) . ?
C3 C5 1.514(3) . ?
C3 C4 1.528(3) . ?
C4 C5 1.529(3) . ?
C4 H3 1.00(3) . ?
C5 C6 1.483(3) . ?
C5 H4 1.00(3) . ?
C6 C7 1.391(3) . ?
C6 C11 1.415(3) . ?
C7 C8 1.394(3) . ?
C7 H5 0.96(3) . ?
C8 C9 1.394(3) . ?
C8 H6 1.01(4) . ?
C9 O1 1.369(3) . ?
C9 C10 1.390(3) . ?
C10 C11 1.401(3) . ?
C10 H7 0.97(3) . ?
C11 C12 1.458(3) . ?
C12 C13 1.344(3) . ?
C12 H8 0.95(3) . ?
C13 H9 0.97(3) . ?
C14 H10 0.94(4) . ?
C14 H11 1.00(3) . ?
C14 H12 1.03(4) . ?
O1 C15 1.428(3) . ?
C15 H13 0.99(3) . ?
C15 H15 1.06(5) . ?
C15 H14 1.00(3) . ?

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
N1 C1 C4 108.90(15) . . ?
N1 C1 S1 126.43(13) . . ?
C4 C1 S1 124.65(13) . . ?
C1 N1 C14 125.74(15) . . ?
C1 N1 C2 114.60(15) . . ?
C14 N1 C2 119.48(15) . . ?
N1 C2 C3 104.24(15) . . ?
N1 C2 H1 107.4(18) . . ?
C3 C2 H1 113.4(19) . . ?
N1 C2 H2 110.1(14) . . ?
C3 C2 H2 111.7(15) . . ?
H1 C2 H2 110(2) . . ?
C13 C3 C5 118.23(18) . . ?
C13 C3 C2 122.31(17) . . ?
C5 C3 C2 114.86(17) . . ?
C13 C3 C4 118.86(18) . . ?
C5 C3 C4 60.33(13) . . ?
C2 C3 C4 105.65(16) . . ?
C1 C4 C3 106.34(15) . . ?
C1 C4 C5 117.12(18) . . ?
C3 C4 C5 59.40(12) . . ?
C1 C4 H3 122.3(16) . . ?
C3 C4 H3 119.0(16) . . ?
C5 C4 H3 115.9(17) . . ?
C6 C5 C3 117.03(17) . . ?
C6 C5 C4 118.13(17) . . ?
C3 C5 C4 60.27(13) . . ?
C6 C5 H4 116.6(16) . . ?
C3 C5 H4 118.1(17) . . ?
C4 C5 H4 114.8(15) . . ?
C7 C6 C11 119.06(19) . . ?
C7 C6 C5 120.72(18) . . ?
C11 C6 C5 120.22(18) . . ?
C6 C7 C8 121.6(2) . . ?
C6 C7 H5 119.4(18) . . ?
C8 C7 H5 119.0(18) . . ?
C9 C8 C7 119.3(2) . . ?
C9 C8 H6 122.7(19) . . ?
C7 C8 H6 118.0(19) . . ?
O1 C9 C10 115.8(2) . . ?
O1 C9 C8 124.2(2) . . ?
C10 C9 C8 119.9(2) . . ?
C9 C10 C11 121.1(2) . . ?
C9 C10 H7 120(2) . . ?
C11 C10 H7 119(2) . . ?
C10 C11 C6 118.9(2) . . ?
C10 C11 C12 120.82(19) . . ?
C6 C11 C12 120.09(18) . . ?
C13 C12 C11 122.0(2) . . ?
C13 C12 H8 118(2) . . ?
C11 C12 H8 120(2) . . ?
C12 C13 C3 121.6(2) . . ?
C12 C13 H9 119.5(19) . . ?
C3 C13 H9 118.6(19) . . ?
N1 C14 H10 107(2) . . ?
N1 C14 H11 110.6(19) . . ?
H10 C14 H11 115(3) . . ?
N1 C14 H12 108.5(19) . . ?
H10 C14 H12 107(3) . . ?
H11 C14 H12 109(3) . . ?
C9 O1 C15 117.49(19) . . ?
O1 C15 H13 106(2) . . ?
O1 C15 H15 109(2) . . ?
H13 C15 H15 108(3) . . ?
O1 C15 H14 110(2) . . ?
H13 C15 H14 112(3) . . ?
H15 C15 H14 113(3) . . ?

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
C4 C1 N1 C14 179.2(2) . . . . ?
S1 C1 N1 C14 -2.6(4) . . . . ?
C4 C1 N1 C2 -5.6(3) . . . . ?
S1 C1 N1 C2 172.59(18) . . . . ?
C1 N1 C2 C3 4.0(3) . . . . ?
C14 N1 C2 C3 179.5(2) . . . . ?
N1 C2 C3 C13 -141.2(2) . . . . ?
N1 C2 C3 C5 63.3(2) . . . . ?
N1 C2 C3 C4 -0.8(2) . . . . ?
N1 C1 C4 C3 4.7(3) . . . . ?
S1 C1 C4 C3 -173.52(16) . . . . ?
N1 C1 C4 C5 -58.9(3) . . . . ?
S1 C1 C4 C5 122.96(19) . . . . ?
C13 C3 C4 C1 139.9(2) . . . . ?
C5 C3 C4 C1 -112.2(2) . . . . ?
C2 C3 C4 C1 -2.2(2) . . . . ?
C13 C3 C4 C5 -107.9(2) . . . . ?
C2 C3 C4 C5 110.05(17) . . . . ?
C13 C3 C5 C6 0.4(3) . . . . ?
C2 C3 C5 C6 156.95(17) . . . . ?
C4 C3 C5 C6 -108.56(19) . . . . ?
C13 C3 C5 C4 109.0(2) . . . . ?
C2 C3 C5 C4 -94.49(18) . . . . ?
C1 C4 C5 C6 -159.57(17) . . . . ?
C3 C4 C5 C6 106.74(19) . . . . ?
C1 C4 C5 C3 93.69(19) . . . . ?
C3 C5 C6 C7 -172.85(17) . . . . ?
C4 C5 C6 C7 118.2(2) . . . . ?
C3 C5 C6 C11 6.8(3) . . . . ?
C4 C5 C6 C11 -62.2(2) . . . . ?
C11 C6 C7 C8 3.7(3) . . . . ?
C5 C6 C7 C8 -176.56(19) . . . . ?
C6 C7 C8 C9 -0.7(3) . . . . ?
C7 C8 C9 O1 177.6(2) . . . . ?
C7 C8 C9 C10 -2.6(3) . . . . ?
O1 C9 C10 C11 -177.44(19) . . . . ?
C8 C9 C10 C11 2.7(3) . . . . ?
C9 C10 C11 C6 0.4(3) . . . . ?
C9 C10 C11 C12 -175.2(2) . . . . ?
C7 C6 C11 C10 -3.6(3) . . . . ?
C5 C6 C11 C10 176.73(18) . . . . ?
C7 C6 C11 C12 172.08(19) . . . . ?
C5 C6 C11 C12 -7.6(3) . . . . ?
C10 C11 C12 C13 176.2(2) . . . . ?
C6 C11 C12 C13 0.6(3) . . . . ?
C11 C12 C13 C3 7.0(3) . . . . ?
C5 C3 C13 C12 -7.3(3) . . . . ?
C2 C3 C13 C12 -162.1(2) . . . . ?
C4 C3 C13 C12 62.4(3) . . . . ?
C10 C9 O1 C15 174.8(2) . . . . ?
C8 C9 O1 C15 -5.3(3) . . . . ?

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
_geom_hbond_publ_flag
C2 H2 S1 1.04(3) 2.75(3) 3.493(2) 127.9(18) 2_756 yes

_refine_diff_density_max         0.289
_refine_diff_density_min         -0.535
_refine_diff_density_rms         0.058


_diffrn_radiation_monochromator  'Graphite Monochromator'
