# Supplementary Information (SI) for RSC Advances.
# 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_Compound_1a
_database_code_depnum_ccdc_archive 'CCDC 2387412'
loop_
_audit_author_name
_audit_author_address
'Mario Macias'
;Departamento de Quimica, Universidad de los Andes, Bogota
Colombia
;
_audit_update_record             
;
2024-09-27 deposited with the CCDC.	2024-12-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H9 N O S3'
_chemical_formula_sum            'C7 H9 N O S3'
_chemical_formula_weight         219.33

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'

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

_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'

_cell_length_a                   11.4682(5)
_cell_length_b                   5.3017(3)
_cell_length_c                   15.1947(7)
_cell_angle_alpha                90
_cell_angle_beta                 91.900(2)
_cell_angle_gamma                90
_cell_volume                     923.34(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9887
_cell_measurement_theta_max      72.00
_cell_measurement_theta_min      3.86

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.578
_exptl_crystal_F_000             456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.595
_exptl_crystal_size_mid          0.134
_exptl_crystal_size_min          0.103
_exptl_absorpt_coefficient_mu    6.941
_shelx_estimated_absorpt_T_min   0.104
_shelx_estimated_absorpt_T_max   0.535
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.4212
_exptl_absorpt_process_details   'SADABS-2016/2 (Bruker,2016/2)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15886
_diffrn_reflns_av_unetI/netI     0.0406
_diffrn_reflns_av_R_equivalents  0.0490
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.910
_diffrn_reflns_theta_max         72.310
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_point_group_measured_fraction_full 0.979
_reflns_number_total             3542
_reflns_number_gt                3270
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.743
_reflns_Friedel_fraction_max     0.932
_reflns_Friedel_fraction_full    0.952

_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       ?
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  ?
_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)+(0.0523P)²+0.3779P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1279 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.070(12)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         3542
_refine_ls_number_parameters     217
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0387
_refine_ls_wR_factor_ref         0.1049
_refine_ls_wR_factor_gt          0.1019
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.001
_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
S3B S 0.10792(10) 1.2641(2) 0.50400(8) 0.0553(3) Uani 1 1 d . . . . .
S10 S 0.55030(10) 0.3627(3) 0.84884(9) 0.0621(3) Uani 1 1 d . . . . .
S10B S 0.39501(11) 0.7074(3) 0.49983(8) 0.0581(3) Uani 1 1 d . . . . .
S6 S 0.88322(11) -0.1885(3) 1.00777(7) 0.0596(4) Uani 1 1 d . . . . .
S3 S 0.81492(12) -0.1374(3) 0.72913(7) 0.0665(4) Uani 1 1 d . . . . .
S6B S 0.18328(13) 1.0804(4) 0.77602(8) 0.0742(4) Uani 1 1 d . . . . .
N1 N 0.7708(3) 0.0628(7) 0.88043(19) 0.0390(7) Uani 1 1 d . . . . .
O1 O 0.5826(3) 0.3858(8) 1.0175(3) 0.0687(10) Uani 1 1 d . . . . .
N1B N 0.2251(3) 0.9585(8) 0.6124(2) 0.0461(9) Uani 1 1 d . . . . .
C5 C 0.8808(3) -0.0753(9) 0.8948(3) 0.0445(10) Uani 1 1 d . . . . .
H5 H 0.945802 0.042300 0.888067 0.053 Uiso 1 1 calc R U . . .
C8 C 0.6959(4) 0.0542(9) 0.9570(3) 0.0436(9) Uani 1 1 d . . . . .
H8 H 0.650005 -0.101659 0.954418 0.052 Uiso 1 1 calc R U . . .
C11 C 0.6402(4) 0.2159(11) 0.7656(3) 0.0587(13) Uani 1 1 d . . . . .
H11A H 0.590636 0.166856 0.715514 0.070 Uiso 1 1 calc R U . . .
H11B H 0.696067 0.338467 0.745345 0.070 Uiso 1 1 calc R U . . .
O1B O 0.4849(5) 0.6310(12) 0.6537(3) 0.1021(19) Uani 1 1 d . . . . .
C9 C 0.6138(4) 0.2756(10) 0.9532(3) 0.0494(10) Uani 1 1 d . . . . .
C2B C 0.2424(4) 1.0952(10) 0.5300(3) 0.0462(10) Uani 1 1 d . . . . .
H2B H 0.306760 1.215542 0.538140 0.055 Uiso 1 1 calc R U . . .
C2 C 0.7052(4) -0.0144(9) 0.8007(3) 0.0443(10) Uani 1 1 d . . . . .
H2 H 0.649650 -0.147686 0.814731 0.053 Uiso 1 1 calc R U . . .
C7 C 0.7768(4) 0.0449(11) 1.0370(3) 0.0568(12) Uani 1 1 d . . . . .
H7A H 0.735604 -0.006034 1.088787 0.068 Uiso 1 1 calc R U . . .
H7B H 0.813287 0.207473 1.047940 0.068 Uiso 1 1 calc R U . . .
C5B C 0.1299(4) 1.0601(11) 0.6625(3) 0.0536(11) Uani 1 1 d . . . . .
H5B H 0.064563 0.940911 0.659216 0.064 Uiso 1 1 calc R U . . .
C4 C 0.8879(4) -0.2781(12) 0.8249(3) 0.0581(12) Uani 1 1 d . . . . .
H4A H 0.848336 -0.430576 0.842734 0.070 Uiso 1 1 calc R U . . .
H4B H 0.968432 -0.318281 0.813120 0.070 Uiso 1 1 calc R U . . .
C8B C 0.3351(4) 0.9360(10) 0.6617(3) 0.0506(11) Uani 1 1 d . . . . .
H8B H 0.374650 1.099886 0.661937 0.061 Uiso 1 1 calc R U . . .
C9B C 0.4110(4) 0.7440(11) 0.6163(3) 0.0572(12) Uani 1 1 d . . . . .
C7B C 0.3058(4) 0.8689(14) 0.7544(3) 0.0638(14) Uani 1 1 d . . . . .
H7BA H 0.371313 0.900443 0.794910 0.077 Uiso 1 1 calc R U . . .
H7BB H 0.282833 0.693371 0.758802 0.077 Uiso 1 1 calc R U . . .
C11B C 0.2727(5) 0.9036(11) 0.4618(3) 0.0591(13) Uani 1 1 d . . . . .
H11C H 0.292847 0.989278 0.408004 0.071 Uiso 1 1 calc R U . . .
H11D H 0.205431 0.797580 0.448817 0.071 Uiso 1 1 calc R U . . .
C4B C 0.0902(5) 1.3085(13) 0.6219(3) 0.0665(14) Uani 1 1 d . . . . .
H4BA H 0.138135 1.446869 0.644012 0.080 Uiso 1 1 calc R U . . .
H4BB H 0.009375 1.342602 0.634588 0.080 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
S3B C2B 1.816(5) . ?
S3B C4B 1.825(5) . ?
S10 C9 1.784(5) . ?
S10 C11 1.831(6) . ?
S10B C9B 1.784(5) . ?
S10B C11B 1.824(5) . ?
S6 C7 1.804(5) . ?
S6 C5 1.818(4) . ?
S3 C2 1.811(5) . ?
S3 C4 1.815(6) . ?
S6B C5B 1.814(5) . ?
S6B C7B 1.836(6) . ?
N1 C2 1.464(5) . ?
N1 C5 1.468(5) . ?
N1 C8 1.470(5) . ?
O1 C9 1.203(6) . ?
N1B C8B 1.451(5) . ?
N1B C5B 1.455(6) . ?
N1B C2B 1.466(6) . ?
C5 C4 1.515(7) . ?
C5 H5 0.9800 . ?
C8 C7 1.505(6) . ?
C8 C9 1.505(6) . ?
C8 H8 0.9800 . ?
C11 C2 1.518(7) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
O1B C9B 1.170(6) . ?
C2B C11B 1.500(7) . ?
C2B H2B 0.9800 . ?
C2 H2 0.9800 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C5B C4B 1.518(8) . ?
C5B H5B 0.9800 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C8B C7B 1.502(6) . ?
C8B C9B 1.519(7) . ?
C8B H8B 0.9800 . ?
C7B H7BA 0.9700 . ?
C7B H7BB 0.9700 . ?
C11B H11C 0.9700 . ?
C11B H11D 0.9700 . ?
C4B H4BA 0.9700 . ?
C4B H4BB 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
C2B S3B C4B 88.4(2) . . ?
C9 S10 C11 106.4(2) . . ?
C9B S10B C11B 107.7(2) . . ?
C7 S6 C5 90.9(2) . . ?
C2 S3 C4 88.7(2) . . ?
C5B S6B C7B 91.7(2) . . ?
C2 N1 C5 113.5(3) . . ?
C2 N1 C8 110.4(3) . . ?
C5 N1 C8 112.9(3) . . ?
C8B N1B C5B 114.5(3) . . ?
C8B N1B C2B 109.9(3) . . ?
C5B N1B C2B 112.9(4) . . ?
N1 C5 C4 108.4(3) . . ?
N1 C5 S6 106.9(3) . . ?
C4 C5 S6 115.3(4) . . ?
N1 C5 H5 108.7 . . ?
C4 C5 H5 108.7 . . ?
S6 C5 H5 108.7 . . ?
N1 C8 C7 106.2(4) . . ?
N1 C8 C9 109.1(4) . . ?
C7 C8 C9 115.2(4) . . ?
N1 C8 H8 108.7 . . ?
C7 C8 H8 108.7 . . ?
C9 C8 H8 108.7 . . ?
C2 C11 S10 112.4(3) . . ?
C2 C11 H11A 109.1 . . ?
S10 C11 H11A 109.1 . . ?
C2 C11 H11B 109.1 . . ?
S10 C11 H11B 109.1 . . ?
H11A C11 H11B 107.9 . . ?
O1 C9 C8 123.4(4) . . ?
O1 C9 S10 118.2(4) . . ?
C8 C9 S10 118.2(3) . . ?
N1B C2B C11B 107.2(4) . . ?
N1B C2B S3B 106.9(3) . . ?
C11B C2B S3B 113.5(3) . . ?
N1B C2B H2B 109.7 . . ?
C11B C2B H2B 109.7 . . ?
S3B C2B H2B 109.7 . . ?
N1 C2 C11 107.4(4) . . ?
N1 C2 S3 104.4(3) . . ?
C11 C2 S3 115.0(3) . . ?
N1 C2 H2 109.9 . . ?
C11 C2 H2 109.9 . . ?
S3 C2 H2 109.9 . . ?
C8 C7 S6 103.2(3) . . ?
C8 C7 H7A 111.1 . . ?
S6 C7 H7A 111.1 . . ?
C8 C7 H7B 111.1 . . ?
S6 C7 H7B 111.1 . . ?
H7A C7 H7B 109.1 . . ?
N1B C5B C4B 109.2(4) . . ?
N1B C5B S6B 106.5(3) . . ?
C4B C5B S6B 115.0(4) . . ?
N1B C5B H5B 108.7 . . ?
C4B C5B H5B 108.7 . . ?
S6B C5B H5B 108.7 . . ?
C5 C4 S3 103.6(4) . . ?
C5 C4 H4A 111.0 . . ?
S3 C4 H4A 111.0 . . ?
C5 C4 H4B 111.0 . . ?
S3 C4 H4B 111.0 . . ?
H4A C4 H4B 109.0 . . ?
N1B C8B C7B 106.6(4) . . ?
N1B C8B C9B 108.8(4) . . ?
C7B C8B C9B 114.6(5) . . ?
N1B C8B H8B 108.9 . . ?
C7B C8B H8B 108.9 . . ?
C9B C8B H8B 108.9 . . ?
O1B C9B C8B 122.7(5) . . ?
O1B C9B S10B 118.3(4) . . ?
C8B C9B S10B 118.8(3) . . ?
C8B C7B S6B 102.7(4) . . ?
C8B C7B H7BA 111.2 . . ?
S6B C7B H7BA 111.2 . . ?
C8B C7B H7BB 111.2 . . ?
S6B C7B H7BB 111.2 . . ?
H7BA C7B H7BB 109.1 . . ?
C2B C11B S10B 111.2(3) . . ?
C2B C11B H11C 109.4 . . ?
S10B C11B H11C 109.4 . . ?
C2B C11B H11D 109.4 . . ?
S10B C11B H11D 109.4 . . ?
H11C C11B H11D 108.0 . . ?
C5B C4B S3B 104.2(4) . . ?
C5B C4B H4BA 110.9 . . ?
S3B C4B H4BA 110.9 . . ?
C5B C4B H4BB 110.9 . . ?
S3B C4B H4BB 110.9 . . ?
H4BA C4B H4BB 108.9 . . ?

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
C2 N1 C5 C4 -5.2(5) . . . . ?
C8 N1 C5 C4 121.5(4) . . . . ?
C2 N1 C5 S6 -130.1(3) . . . . ?
C8 N1 C5 S6 -3.5(4) . . . . ?
C7 S6 C5 N1 -20.6(3) . . . . ?
C7 S6 C5 C4 -141.3(4) . . . . ?
C2 N1 C8 C7 160.5(4) . . . . ?
C5 N1 C8 C7 32.2(5) . . . . ?
C2 N1 C8 C9 -74.8(5) . . . . ?
C5 N1 C8 C9 156.9(4) . . . . ?
C9 S10 C11 C2 24.3(4) . . . . ?
N1 C8 C9 O1 -144.9(5) . . . . ?
C7 C8 C9 O1 -25.6(7) . . . . ?
N1 C8 C9 S10 40.4(5) . . . . ?
C7 C8 C9 S10 159.6(4) . . . . ?
C11 S10 C9 O1 166.9(4) . . . . ?
C11 S10 C9 C8 -18.1(4) . . . . ?
C8B N1B C2B C11B 88.9(5) . . . . ?
C5B N1B C2B C11B -141.9(4) . . . . ?
C8B N1B C2B S3B -149.1(3) . . . . ?
C5B N1B C2B S3B -19.9(5) . . . . ?
C4B S3B C2B N1B 34.4(4) . . . . ?
C4B S3B C2B C11B 152.4(4) . . . . ?
C5 N1 C2 C11 -148.2(4) . . . . ?
C8 N1 C2 C11 83.9(4) . . . . ?
C5 N1 C2 S3 -25.7(4) . . . . ?
C8 N1 C2 S3 -153.6(3) . . . . ?
S10 C11 C2 N1 -54.0(4) . . . . ?
S10 C11 C2 S3 -169.7(2) . . . . ?
C4 S3 C2 N1 38.8(3) . . . . ?
C4 S3 C2 C11 156.2(4) . . . . ?
N1 C8 C7 S6 -45.5(5) . . . . ?
C9 C8 C7 S6 -166.4(3) . . . . ?
C5 S6 C7 C8 38.0(4) . . . . ?
C8B N1B C5B C4B 116.9(5) . . . . ?
C2B N1B C5B C4B -10.0(5) . . . . ?
C8B N1B C5B S6B -7.8(5) . . . . ?
C2B N1B C5B S6B -134.7(3) . . . . ?
C7B S6B C5B N1B -16.2(4) . . . . ?
C7B S6B C5B C4B -137.3(4) . . . . ?
N1 C5 C4 S3 33.4(4) . . . . ?
S6 C5 C4 S3 153.2(2) . . . . ?
C2 S3 C4 C5 -41.7(3) . . . . ?
C5B N1B C8B C7B 34.7(6) . . . . ?
C2B N1B C8B C7B 163.1(4) . . . . ?
C5B N1B C8B C9B 158.7(4) . . . . ?
C2B N1B C8B C9B -72.9(5) . . . . ?
N1B C8B C9B O1B -155.1(6) . . . . ?
C7B C8B C9B O1B -35.9(8) . . . . ?
N1B C8B C9B S10B 30.2(6) . . . . ?
C7B C8B C9B S10B 149.4(4) . . . . ?
C11B S10B C9B O1B 179.5(6) . . . . ?
C11B S10B C9B C8B -5.5(5) . . . . ?
N1B C8B C7B S6B -43.5(5) . . . . ?
C9B C8B C7B S6B -163.9(4) . . . . ?
C5B S6B C7B C8B 34.3(4) . . . . ?
N1B C2B C11B S10B -53.1(4) . . . . ?
S3B C2B C11B S10B -171.0(3) . . . . ?
C9B S10B C11B C2B 16.8(5) . . . . ?
N1B C5B C4B S3B 34.8(5) . . . . ?
S6B C5B C4B S3B 154.4(3) . . . . ?
C2B S3B C4B C5B -39.3(4) . . . . ?

_refine_diff_density_max         0.421
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.053

####################################################################### 
# 
# 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_Compound_1c
_database_code_depnum_ccdc_archive 'CCDC 2387413'
loop_
_audit_author_name
_audit_author_address
'Mario Macias'
;Departamento de Quimica, Universidad de los Andes, Bogota
Colombia
;
_audit_update_record             
;
2024-09-27 deposited with the CCDC.	2024-12-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H9 N O S3'
_chemical_formula_sum            'C7 H9 N O S3'
_chemical_formula_weight         219.33

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.2493(7)
_cell_length_b                   12.0624(18)
_cell_length_c                   14.1479(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     895.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9466
_cell_measurement_theta_min      2.878
_cell_measurement_theta_max      26.59

_exptl_crystal_description       paralellepiped
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.626
_exptl_crystal_F_000             456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.774
_shelx_estimated_absorpt_T_min   0.757
_shelx_estimated_absorpt_T_max   0.941
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.814
_exptl_absorpt_correction_T_max  0.941
_exptl_absorpt_process_details   'SADABS-2016/2 (Bruker,2016/2)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29567
_diffrn_reflns_av_unetI/netI     0.0197
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.880
_diffrn_reflns_theta_max         26.601
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1863
_reflns_number_gt                1775
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.669
_reflns_Friedel_fraction_max     0.987
_reflns_Friedel_fraction_full    0.998

_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       ?
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  ?
_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)+(0.0113P)²+1.1511P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 676 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(4)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         1863
_refine_ls_number_parameters     109
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0381
_refine_ls_wR_factor_ref         0.0873
_refine_ls_wR_factor_gt          0.0863
_refine_ls_goodness_of_fit_ref   1.253
_refine_ls_restrained_S_all      1.253
_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
S10 S 0.2202(2) 0.67081(10) 0.70466(11) 0.0472(3) Uani 1 1 d . . . . .
N1 N 0.6015(6) 0.4890(3) 0.6279(2) 0.0243(7) Uani 1 1 d . . . . .
O1 O 0.1588(6) 0.6712(3) 0.5232(3) 0.0558(11) Uani 1 1 d . . . . .
C9 C 0.3007(8) 0.6446(3) 0.5857(4) 0.0354(11) Uani 1 1 d . . . . .
C8 C 0.5616(8) 0.5906(3) 0.5714(3) 0.0279(9) Uani 1 1 d . . . . .
H8 H 0.692595 0.644489 0.589369 0.034 Uiso 1 1 calc R U . . .
S6 S 0.4857(3) 0.41760(12) 0.45774(9) 0.0553(4) Uani 1 1 d . . . . .
C7 C 0.6080(10) 0.5570(4) 0.4705(3) 0.0432(12) Uani 1 1 d . . . . .
H7A H 0.788727 0.558841 0.456350 0.052 Uiso 1 1 calc R U . . .
H7B H 0.520618 0.606983 0.427724 0.052 Uiso 1 1 calc R U . . .
S3 S 0.2636(3) 0.39872(10) 0.74930(9) 0.0430(3) Uani 1 1 d . . . . .
C5 C 0.4841(9) 0.3919(3) 0.5838(3) 0.0320(9) Uani 1 1 d . . . . .
H5 H 0.588003 0.326337 0.597380 0.038 Uiso 1 1 calc R U . . .
C4 C 0.2178(10) 0.3753(4) 0.6251(3) 0.0383(11) Uani 1 1 d . . . . .
H4A H 0.156180 0.300821 0.613210 0.046 Uiso 1 1 calc R U . . .
H4B H 0.097982 0.428204 0.598741 0.046 Uiso 1 1 calc R U . . .
C2 C 0.5401(8) 0.4925(3) 0.7282(3) 0.0304(9) Uani 1 1 d . . . . .
H2 H 0.686244 0.463030 0.763207 0.036 Uiso 1 1 calc R U . . .
C11 C 0.4911(9) 0.6090(4) 0.7625(3) 0.0384(10) Uani 1 1 d . . . . .
H11A H 0.640792 0.654101 0.750810 0.046 Uiso 1 1 calc R U . . .
H11B H 0.461612 0.607646 0.830213 0.046 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
S10 C9 1.764(5) . ?
S10 C11 1.803(5) . ?
N1 C2 1.456(5) . ?
N1 C5 1.462(5) . ?
N1 C8 1.478(5) . ?
O1 C9 1.200(5) . ?
C9 C8 1.530(6) . ?
C8 C7 1.504(6) . ?
C8 H8 0.9800 . ?
S6 C7 1.808(5) . ?
S6 C5 1.810(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
S3 C4 1.796(5) . ?
S3 C2 1.864(5) . ?
C5 C4 1.529(7) . ?
C5 H5 0.9800 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C2 C11 1.509(6) . ?
C2 H2 0.9800 . ?
C11 H11A 0.9700 . ?
C11 H11B 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
C9 S10 C11 99.8(2) . . ?
C2 N1 C5 110.2(3) . . ?
C2 N1 C8 118.1(3) . . ?
C5 N1 C8 111.9(3) . . ?
O1 C9 C8 124.9(5) . . ?
O1 C9 S10 120.5(4) . . ?
C8 C9 S10 114.6(3) . . ?
N1 C8 C7 105.5(4) . . ?
N1 C8 C9 114.2(3) . . ?
C7 C8 C9 112.7(4) . . ?
N1 C8 H8 108.1 . . ?
C7 C8 H8 108.1 . . ?
C9 C8 H8 108.1 . . ?
C7 S6 C5 93.6(2) . . ?
C8 C7 S6 106.7(3) . . ?
C8 C7 H7A 110.4 . . ?
S6 C7 H7A 110.4 . . ?
C8 C7 H7B 110.4 . . ?
S6 C7 H7B 110.4 . . ?
H7A C7 H7B 108.6 . . ?
C4 S3 C2 92.5(2) . . ?
N1 C5 C4 109.1(3) . . ?
N1 C5 S6 106.3(3) . . ?
C4 C5 S6 113.8(3) . . ?
N1 C5 H5 109.2 . . ?
C4 C5 H5 109.2 . . ?
S6 C5 H5 109.2 . . ?
C5 C4 S3 103.3(3) . . ?
C5 C4 H4A 111.1 . . ?
S3 C4 H4A 111.1 . . ?
C5 C4 H4B 111.1 . . ?
S3 C4 H4B 111.1 . . ?
H4A C4 H4B 109.1 . . ?
N1 C2 C11 112.3(3) . . ?
N1 C2 S3 108.1(3) . . ?
C11 C2 S3 112.4(3) . . ?
N1 C2 H2 108.0 . . ?
C11 C2 H2 108.0 . . ?
S3 C2 H2 108.0 . . ?
C2 C11 S10 111.9(3) . . ?
C2 C11 H11A 109.2 . . ?
S10 C11 H11A 109.2 . . ?
C2 C11 H11B 109.2 . . ?
S10 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?

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
C11 S10 C9 O1 177.7(4) . . . . ?
C11 S10 C9 C8 -4.1(3) . . . . ?
C2 N1 C8 C7 -172.8(3) . . . . ?
C5 N1 C8 C7 -43.2(5) . . . . ?
C2 N1 C8 C9 -48.6(5) . . . . ?
C5 N1 C8 C9 81.0(4) . . . . ?
O1 C9 C8 N1 -129.3(4) . . . . ?
S10 C9 C8 N1 52.6(4) . . . . ?
O1 C9 C8 C7 -9.0(6) . . . . ?
S10 C9 C8 C7 172.8(3) . . . . ?
N1 C8 C7 S6 36.4(4) . . . . ?
C9 C8 C7 S6 -88.8(4) . . . . ?
C5 S6 C7 C8 -18.2(4) . . . . ?
C2 N1 C5 C4 39.5(5) . . . . ?
C8 N1 C5 C4 -94.1(4) . . . . ?
C2 N1 C5 S6 162.6(3) . . . . ?
C8 N1 C5 S6 29.0(4) . . . . ?
C7 S6 C5 N1 -5.3(3) . . . . ?
C7 S6 C5 C4 114.8(3) . . . . ?
N1 C5 C4 S3 -42.8(4) . . . . ?
S6 C5 C4 S3 -161.3(2) . . . . ?
C2 S3 C4 C5 27.4(3) . . . . ?
C5 N1 C2 C11 -141.5(4) . . . . ?
C8 N1 C2 C11 -11.1(5) . . . . ?
C5 N1 C2 S3 -17.0(4) . . . . ?
C8 N1 C2 S3 113.4(3) . . . . ?
C4 S3 C2 N1 -7.3(3) . . . . ?
C4 S3 C2 C11 117.2(3) . . . . ?
N1 C2 C11 S10 62.4(4) . . . . ?
S3 C2 C11 S10 -59.7(4) . . . . ?
C9 S10 C11 C2 -50.8(4) . . . . ?

_refine_diff_density_max         0.359
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.073

