# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_YC2-9-no-SS
_database_code_depnum_ccdc_archive 'CCDC 2332996'
loop_
_audit_author_name
_audit_author_address
'Tadashi Hyodo'
;Tokushima Bunri University
Japan
;
_audit_update_record             
;
2024-02-15 deposited with the CCDC.	2024-05-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        YC2-9-no-SS
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H17 N O S2'
_chemical_formula_weight         243.37

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           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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                   15.8974(17)
_cell_length_b                   7.8350(8)
_cell_length_c                   9.4791(10)
_cell_angle_alpha                90
_cell_angle_beta                 100.6820(10)
_cell_angle_gamma                90
_cell_volume                     1160.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6866
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      26.82

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_F_000             520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.432
_shelx_estimated_absorpt_T_min   0.881
_shelx_estimated_absorpt_T_max   0.919
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8477
_exptl_absorpt_correction_T_max  0.9281
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX II CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            10161
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.303
_diffrn_reflns_theta_max         26.120
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.930
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.930
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.930
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             2150
_reflns_number_gt                1956
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'APEX2 (Bruker AXS, 2006)'
_computing_cell_refinement       'SAINT (Bruker AXS, 2004)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXLE (Hübschle et al., 2011)'
_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)+(0.0301P)²+1.9523P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2150
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0460
_refine_ls_wR_factor_ref         0.1078
_refine_ls_wR_factor_gt          0.1043
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_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
C1 C 0.28877(13) 0.7898(3) 0.7061(2) 0.0184(4) Uani 1 1 d . . . . .
C2 C 0.21975(14) 0.8073(3) 0.7947(2) 0.0261(5) Uani 1 1 d . . . . .
H2A H 0.242258 0.875291 0.881577 0.031 Uiso 1 1 calc R U . . .
H2AB H 0.205033 0.692556 0.826536 0.031 Uiso 1 1 calc R U . . .
C3 C 0.13897(17) 0.8921(4) 0.7141(3) 0.0441(7) Uani 1 1 d . . . . .
H3A H 0.104585 0.933044 0.784341 0.053 Uiso 1 1 calc R U . . .
H3AB H 0.155269 0.992762 0.662091 0.053 Uiso 1 1 calc R U . . .
C4 C 0.08409(17) 0.7742(4) 0.6075(3) 0.0415(7) Uani 1 1 d . . . . .
H4A H 0.116189 0.742945 0.531188 0.050 Uiso 1 1 calc R U . . .
H4AB H 0.031800 0.836062 0.561706 0.050 Uiso 1 1 calc R U . . .
C5 C 0.22871(16) 0.3933(3) 0.7749(3) 0.0329(6) Uani 1 1 d . . . . .
H5A H 0.218123 0.463292 0.856794 0.039 Uiso 1 1 calc R U . . .
H5AB H 0.238838 0.274559 0.809750 0.039 Uiso 1 1 calc R U . . .
C6 C 0.30932(14) 0.4579(3) 0.7290(2) 0.0200(5) Uani 1 1 d . . . . .
C7 C 0.32888(19) 0.3536(3) 0.6006(3) 0.0366(6) Uani 1 1 d . . . . .
H7A H 0.351666 0.239374 0.632044 0.044 Uiso 1 1 calc R U . . .
H7AB H 0.276781 0.339432 0.526144 0.044 Uiso 1 1 calc R U . . .
C8 C 0.39634(17) 0.4601(3) 0.5437(2) 0.0354(6) Uani 1 1 d . . . . .
H8A H 0.451578 0.398686 0.554405 0.042 Uiso 1 1 calc R U . . .
H8AB H 0.376855 0.490887 0.441593 0.042 Uiso 1 1 calc R U . . .
C9 C 0.40364(14) 0.6170(3) 0.6398(2) 0.0230(5) Uani 1 1 d . . . . .
H9 H 0.425331 0.721374 0.597403 0.028 Uiso 1 1 calc R U . . .
C10 C 0.45358(14) 0.5690(3) 0.7900(2) 0.0274(5) Uani 1 1 d . . . . .
H10A H 0.467677 0.671435 0.850872 0.033 Uiso 1 1 calc R U . . .
H10B H 0.507071 0.507314 0.783400 0.033 Uiso 1 1 calc R U . . .
C11 C 0.38962(14) 0.4517(3) 0.8492(2) 0.0235(5) Uani 1 1 d . . . . .
H11A H 0.412053 0.333939 0.864248 0.028 Uiso 1 1 calc R U . . .
H11B H 0.377026 0.496198 0.940784 0.028 Uiso 1 1 calc R U . . .
N1 N 0.31554(10) 0.6339(2) 0.67072(17) 0.0146(4) Uani 1 1 d . . . . .
O1 O 0.32037(12) 0.9200(2) 0.6655(2) 0.0350(4) Uani 1 1 d . . . . .
S1 S 0.05323(4) 0.58044(14) 0.69050(8) 0.0559(3) Uani 1 1 d . . . . .
S2 S 0.13174(5) 0.39638(10) 0.63526(8) 0.0482(2) Uani 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
C1 O1 1.230(3) . ?
C1 N1 1.356(3) . ?
C1 C2 1.507(3) . ?
C2 C3 1.520(3) . ?
C2 H2A 0.9900 . ?
C2 H2AB 0.9900 . ?
C3 C4 1.519(4) . ?
C3 H3A 0.9900 . ?
C3 H3AB 0.9900 . ?
C4 S1 1.819(3) . ?
C4 H4A 0.9900 . ?
C4 H4AB 0.9900 . ?
C5 C6 1.515(3) . ?
C5 S2 1.837(2) . ?
C5 H5A 0.9900 . ?
C5 H5AB 0.9900 . ?
C6 N1 1.496(3) . ?
C6 C7 1.545(3) . ?
C6 C11 1.546(3) . ?
C7 C8 1.534(4) . ?
C7 H7A 0.9900 . ?
C7 H7AB 0.9900 . ?
C8 C9 1.522(3) . ?
C8 H8A 0.9900 . ?
C8 H8AB 0.9900 . ?
C9 N1 1.489(3) . ?
C9 C10 1.543(3) . ?
C9 H9 1.0000 . ?
C10 C11 1.551(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
S1 S2 2.0381(14) . ?

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 C1 N1 120.32(19) . . ?
O1 C1 C2 118.7(2) . . ?
N1 C1 C2 120.97(19) . . ?
C1 C2 C3 113.2(2) . . ?
C1 C2 H2A 108.9 . . ?
C3 C2 H2A 108.9 . . ?
C1 C2 H2AB 108.9 . . ?
C3 C2 H2AB 108.9 . . ?
H2A C2 H2AB 107.8 . . ?
C4 C3 C2 113.4(2) . . ?
C4 C3 H3A 108.9 . . ?
C2 C3 H3A 108.9 . . ?
C4 C3 H3AB 108.9 . . ?
C2 C3 H3AB 108.9 . . ?
H3A C3 H3AB 107.7 . . ?
C3 C4 S1 112.8(2) . . ?
C3 C4 H4A 109.0 . . ?
S1 C4 H4A 109.0 . . ?
C3 C4 H4AB 109.0 . . ?
S1 C4 H4AB 109.0 . . ?
H4A C4 H4AB 107.8 . . ?
C6 C5 S2 115.48(16) . . ?
C6 C5 H5A 108.4 . . ?
S2 C5 H5A 108.4 . . ?
C6 C5 H5AB 108.4 . . ?
S2 C5 H5AB 108.4 . . ?
H5A C5 H5AB 107.5 . . ?
N1 C6 C5 122.11(19) . . ?
N1 C6 C7 99.21(16) . . ?
C5 C6 C7 110.7(2) . . ?
N1 C6 C11 101.47(16) . . ?
C5 C6 C11 113.89(17) . . ?
C7 C6 C11 107.73(19) . . ?
C8 C7 C6 104.19(19) . . ?
C8 C7 H7A 110.9 . . ?
C6 C7 H7A 110.9 . . ?
C8 C7 H7AB 110.9 . . ?
C6 C7 H7AB 110.9 . . ?
H7A C7 H7AB 108.9 . . ?
C9 C8 C7 102.13(18) . . ?
C9 C8 H8A 111.3 . . ?
C7 C8 H8A 111.3 . . ?
C9 C8 H8AB 111.3 . . ?
C7 C8 H8AB 111.3 . . ?
H8A C8 H8AB 109.2 . . ?
N1 C9 C8 102.67(18) . . ?
N1 C9 C10 100.49(16) . . ?
C8 C9 C10 108.91(19) . . ?
N1 C9 H9 114.4 . . ?
C8 C9 H9 114.4 . . ?
C10 C9 H9 114.4 . . ?
C9 C10 C11 102.64(17) . . ?
C9 C10 H10A 111.2 . . ?
C11 C10 H10A 111.2 . . ?
C9 C10 H10B 111.2 . . ?
C11 C10 H10B 111.2 . . ?
H10A C10 H10B 109.2 . . ?
C6 C11 C10 102.84(16) . . ?
C6 C11 H11A 111.2 . . ?
C10 C11 H11A 111.2 . . ?
C6 C11 H11B 111.2 . . ?
C10 C11 H11B 111.2 . . ?
H11A C11 H11B 109.1 . . ?
C1 N1 C9 118.58(17) . . ?
C1 N1 C6 133.94(17) . . ?
C9 N1 C6 96.89(16) . . ?
C4 S1 S2 104.62(9) . . ?
C5 S2 S1 107.24(10) . . ?

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
O1 C1 C2 C3 64.0(3) . . . . ?
N1 C1 C2 C3 -115.7(2) . . . . ?
C1 C2 C3 C4 76.6(3) . . . . ?
C2 C3 C4 S1 56.7(3) . . . . ?
S2 C5 C6 N1 58.2(3) . . . . ?
S2 C5 C6 C7 -57.9(2) . . . . ?
S2 C5 C6 C11 -179.50(16) . . . . ?
N1 C6 C7 C8 36.5(2) . . . . ?
C5 C6 C7 C8 166.07(19) . . . . ?
C11 C6 C7 C8 -68.8(2) . . . . ?
C6 C7 C8 C9 -3.2(2) . . . . ?
C7 C8 C9 N1 -31.7(2) . . . . ?
C7 C8 C9 C10 74.2(2) . . . . ?
N1 C9 C10 C11 37.4(2) . . . . ?
C8 C9 C10 C11 -70.0(2) . . . . ?
N1 C6 C11 C10 -31.3(2) . . . . ?
C5 C6 C11 C10 -164.34(19) . . . . ?
C7 C6 C11 C10 72.4(2) . . . . ?
C9 C10 C11 C6 -3.6(2) . . . . ?
O1 C1 N1 C9 25.7(3) . . . . ?
C2 C1 N1 C9 -154.63(19) . . . . ?
O1 C1 N1 C6 161.3(2) . . . . ?
C2 C1 N1 C6 -19.0(3) . . . . ?
C8 C9 N1 C1 -155.30(18) . . . . ?
C10 C9 N1 C1 92.4(2) . . . . ?
C8 C9 N1 C6 55.18(18) . . . . ?
C10 C9 N1 C6 -57.12(19) . . . . ?
C5 C6 N1 C1 41.0(3) . . . . ?
C7 C6 N1 C1 162.7(2) . . . . ?
C11 C6 N1 C1 -86.9(3) . . . . ?
C5 C6 N1 C9 -177.17(19) . . . . ?
C7 C6 N1 C9 -55.48(19) . . . . ?
C11 C6 N1 C9 54.86(18) . . . . ?
C3 C4 S1 S2 -102.93(18) . . . . ?
C6 C5 S2 S1 -110.42(18) . . . . ?

_refine_diff_density_max         0.468
_refine_diff_density_min         -0.933
_refine_diff_density_rms         0.061



