# Supplementary Information (SI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_230622b
_database_code_depnum_ccdc_archive 'CCDC 2288291'
loop_
_audit_author_name
_audit_author_address
'Minghong Liao'
;Guizhou University
China
;
_audit_update_record             
;
2024-01-31 deposited with the CCDC.	2025-01-15 downloaded from the CCDC.
;
_audit_creation_date             2024-01-30
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C7 H9 N O S'
_chemical_formula_sum            'C7 H9 N O S'
_chemical_formula_weight         155.21
_chemical_absolute_configuration unk
_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 0.0033 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'

_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   4.9512(6)
_cell_length_b                   6.4395(8)
_cell_length_c                   24.625(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     785.11(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1846
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.465
_cell_measurement_theta_min      2.491
_shelx_estimated_absorpt_T_max   0.967
_shelx_estimated_absorpt_T_min   0.853
_exptl_absorpt_coefficient_mu    0.341
_exptl_absorpt_correction_T_max  0.9667
_exptl_absorpt_correction_T_min  0.8533
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1247
_diffrn_reflns_av_unetI/netI     0.0993
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            3718
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.006
_diffrn_reflns_theta_max         25.006
_diffrn_reflns_theta_min         3.270
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.624
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                1255
_reflns_number_total             1374
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.072
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.1(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.143
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     93
_refine_ls_number_reflns         1374
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0729
_refine_ls_R_factor_gt           0.0676
_refine_ls_restrained_S_all      1.143
_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)+(0.0661P)²+0.5559P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1703
_refine_ls_wR_factor_ref         0.1735
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.9(3)
 0.1(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All N(H,H) groups
3.a Riding coordinates:
 N1(H1A,H1B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6)
3.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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 0.8225(3) 0.2915(3) 0.80725(6) 0.0400(5) Uani 1 1 d . . . . .
O1 O 0.7785(10) 0.4118(8) 0.75595(17) 0.0500(12) Uani 1 1 d . . . . .
N1 N 0.7288(11) 0.0467(9) 0.8011(2) 0.0457(14) Uani 1 1 d . . . . .
H1A H 0.866677 -0.027937 0.788542 0.068 Uiso 1 1 d R U . . .
H1B H 0.592127 0.040273 0.777692 0.068 Uiso 1 1 d R U . . .
C1 C 0.5562(12) 0.3757(10) 0.8508(2) 0.0379(15) Uani 1 1 d . . . . .
C2 C 0.4539(14) 0.5713(10) 0.8427(3) 0.0446(16) Uani 1 1 d . . . . .
H2 H 0.514589 0.651907 0.813837 0.053 Uiso 1 1 calc R U . . .
C3 C 0.2581(14) 0.6484(11) 0.8782(3) 0.0494(18) Uani 1 1 d . . . . .
H3 H 0.186357 0.779777 0.872020 0.059 Uiso 1 1 calc R U . . .
C4 C 0.1690(15) 0.5359(12) 0.9216(3) 0.0502(18) Uani 1 1 d . . . . .
C5 C 0.2747(14) 0.3396(12) 0.9291(3) 0.053(2) Uani 1 1 d . . . . .
H5 H 0.213756 0.259539 0.958093 0.063 Uiso 1 1 calc R U . . .
C6 C 0.4684(14) 0.2594(12) 0.8948(2) 0.0487(18) Uani 1 1 d . . . . .
H6 H 0.539668 0.128000 0.901059 0.058 Uiso 1 1 calc R U . . .
C7 C -0.0455(17) 0.6198(15) 0.9595(3) 0.070(3) Uani 1 1 d . . . . .
H7A H -0.005588 0.577819 0.996055 0.105 Uiso 1 1 calc R U . . .
H7B H -0.218774 0.566023 0.949086 0.105 Uiso 1 1 calc R U . . .
H7C H -0.048237 0.768626 0.957458 0.105 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0244(7) 0.0500(10) 0.0455(8) 0.0002(7) 0.0044(7) -0.0060(7)
O1 0.039(3) 0.057(3) 0.054(2) 0.007(2) 0.013(2) -0.004(3)
N1 0.033(3) 0.049(3) 0.055(3) -0.007(3) 0.002(2) -0.003(3)
C1 0.029(3) 0.043(4) 0.042(3) -0.004(3) 0.001(2) -0.012(3)
C2 0.052(4) 0.037(3) 0.045(3) -0.002(3) 0.011(3) 0.004(4)
C3 0.042(4) 0.043(4) 0.063(4) -0.013(3) 0.001(3) 0.010(3)
C4 0.032(3) 0.065(5) 0.054(4) -0.023(3) 0.003(3) -0.004(4)
C5 0.039(4) 0.071(5) 0.047(3) 0.005(3) 0.014(3) -0.002(4)
C6 0.043(4) 0.057(5) 0.046(3) 0.009(3) 0.002(3) 0.009(4)
C7 0.045(5) 0.095(7) 0.071(5) -0.035(5) 0.010(4) -0.009(5)

_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 O1 1.498(5) . ?
S1 N1 1.650(6) . ?
S1 C1 1.784(6) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8899 . ?
C1 C2 1.372(9) . ?
C1 C6 1.386(9) . ?
C2 H2 0.9300 . ?
C2 C3 1.396(9) . ?
C3 H3 0.9300 . ?
C3 C4 1.365(10) . ?
C4 C5 1.381(10) . ?
C4 C7 1.514(10) . ?
C5 H5 0.9300 . ?
C5 C6 1.379(9) . ?
C6 H6 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 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
O1 S1 N1 112.1(3) . . ?
O1 S1 C1 104.0(3) . . ?
N1 S1 C1 97.9(3) . . ?
S1 N1 H1A 109.4 . . ?
S1 N1 H1B 108.5 . . ?
H1A N1 H1B 109.5 . . ?
C2 C1 S1 117.7(5) . . ?
C2 C1 C6 119.6(6) . . ?
C6 C1 S1 122.5(5) . . ?
C1 C2 H2 120.3 . . ?
C1 C2 C3 119.5(6) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 H3 119.1 . . ?
C4 C3 C2 121.7(6) . . ?
C4 C3 H3 119.1 . . ?
C3 C4 C5 118.0(6) . . ?
C3 C4 C7 121.4(7) . . ?
C5 C4 C7 120.6(7) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 C4 121.6(6) . . ?
C6 C5 H5 119.2 . . ?
C1 C6 H6 120.2 . . ?
C5 C6 C1 119.7(7) . . ?
C5 C6 H6 120.2 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 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
S1 C1 C2 C3 -175.8(5) . . . . ?
S1 C1 C6 C5 175.5(5) . . . . ?
O1 S1 C1 C2 -27.3(6) . . . . ?
O1 S1 C1 C6 158.7(6) . . . . ?
N1 S1 C1 C2 -142.5(5) . . . . ?
N1 S1 C1 C6 43.4(6) . . . . ?
C1 C2 C3 C4 1.4(11) . . . . ?
C2 C1 C6 C5 1.5(10) . . . . ?
C2 C3 C4 C5 -1.3(11) . . . . ?
C2 C3 C4 C7 -179.4(6) . . . . ?
C3 C4 C5 C6 1.3(11) . . . . ?
C4 C5 C6 C1 -1.4(11) . . . . ?
C6 C1 C2 C3 -1.5(10) . . . . ?
C7 C4 C5 C6 179.4(7) . . . . ?

_shelx_res_file                  
;
TITL 230622b in P2(1)2(1)2(1)
    230622b.res
    created by SHELXL-2018/3 at 21:41:28 on 30-Jan-2024
CELL 0.71073 4.9512 6.4395 24.6245 90 90 90
ZERR 4 0.0006 0.0008 0.0026 0 0 0
LATT -1
SYMM 0.5-X,-Y,0.5+Z
SYMM 0.5+X,0.5-Y,-Z
SYMM -X,0.5+Y,0.5-Z
SFAC C H N O S
UNIT 28 36 4 4 4

L.S. 40
PLAN  3
SIZE 0.48 0.35 0.1
TEMP 20(2)
CONF
BOND $h
htab
MORE -1
fmap 2
acta
TWIN -1 0 0 0 -1 0 0 0 -1 2
OMIT -1 50.04
OMIT -5 4 2
OMIT -4 2 19
OMIT -3 1 13
OMIT -3 5 14
OMIT 0 1 22
OMIT 1 0 13
OMIT 1 0 23
OMIT 2 0 15
OMIT 2 0 17
OMIT 4 0 4
OMIT 5 3 0
REM <olex2.extras>
REM <HklSrc "%.\\230622b.hkl">
REM </olex2.extras>

WGHT    0.066100    0.555900
BASF   0.08127
FVAR       0.35310
S1    5    0.822521    0.291465    0.807245    11.00000    0.02444    0.04999 =
         0.04546    0.00019    0.00437   -0.00601
O1    4    0.778534    0.411817    0.755954    11.00000    0.03908    0.05733 =
         0.05356    0.00656    0.01256   -0.00357
N1    3    0.728847    0.046683    0.801092    11.00000    0.03261    0.04901 =
         0.05537   -0.00660    0.00207   -0.00296
AFIX   3
H1A   2    0.866677   -0.027937    0.788542    11.00000   -1.50000
H1B   2    0.592127    0.040273    0.777692    11.00000   -1.50000
AFIX   0
C1    1    0.556249    0.375691    0.850817    11.00000    0.02891    0.04267 =
         0.04209   -0.00353    0.00124   -0.01218
C2    1    0.453930    0.571331    0.842710    11.00000    0.05177    0.03734 =
         0.04464   -0.00219    0.01074    0.00450
AFIX  43
H2    2    0.514589    0.651907    0.813837    11.00000   -1.20000
AFIX   0
C3    1    0.258060    0.648373    0.878159    11.00000    0.04217    0.04280 =
         0.06310   -0.01290    0.00071    0.00989
AFIX  43
H3    2    0.186357    0.779777    0.872020    11.00000   -1.20000
AFIX   0
C4    1    0.169050    0.535919    0.921583    11.00000    0.03158    0.06528 =
         0.05363   -0.02269    0.00264   -0.00430
C5    1    0.274654    0.339608    0.929144    11.00000    0.03902    0.07130 =
         0.04724    0.00458    0.01377   -0.00215
AFIX  43
H5    2    0.213756    0.259539    0.958093    11.00000   -1.20000
AFIX   0
C6    1    0.468370    0.259431    0.894772    11.00000    0.04329    0.05727 =
         0.04566    0.00860    0.00244    0.00903
AFIX  43
H6    2    0.539668    0.128000    0.901059    11.00000   -1.20000
AFIX   0
C7    1   -0.045520    0.619769    0.959516    11.00000    0.04454    0.09501 =
         0.07061   -0.03451    0.00987   -0.00894
AFIX 137
H7A   2   -0.005588    0.577819    0.996055    11.00000   -1.50000
H7B   2   -0.218774    0.566023    0.949086    11.00000   -1.50000
H7C   2   -0.048237    0.768626    0.957458    11.00000   -1.50000
AFIX   0
HKLF 4




REM  230622b in P2(1)2(1)2(1)
REM wR2 = 0.1735, GooF = S = 1.143, Restrained GooF = 1.143 for all data
REM R1 = 0.0676 for 1255 Fo > 4sig(Fo) and 0.0729 for all 1374 data
REM 93 parameters refined using 0 restraints

END

WGHT      0.0661      0.5559

REM Instructions for potential hydrogen bonds
EQIV $1 -x+2, y-1/2, -z+3/2
HTAB N1 O1_$1
EQIV $2 -x+1, y-1/2, -z+3/2
HTAB N1 O1_$2

REM Highest difference peak  0.324,  deepest hole -0.371,  1-sigma level  0.072
Q1    1   0.8196  0.2052  0.7555  11.00000  0.05    0.32
Q2    1   0.8166  0.5019  0.8027  11.00000  0.05    0.30
Q3    1   0.8327  0.3775  0.7702  11.00000  0.05    0.28
;
_shelx_res_checksum              10251
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.9(3)
2 0.1(3)

