# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_Glebs236
_database_code_depnum_ccdc_archive 'CCDC 2374035'
loop_
_audit_author_name
_audit_author_address
'Sergey Belyakov'
;Latvian Institute of Organic Synthesis
Latvia
;
_audit_update_record             
;
2024-07-28 deposited with the CCDC.	2024-11-13 downloaded from the CCDC.
;
_audit_creation_date             2022-12-15
_audit_creation_method           
;
Olex2 1.2-ac4
(compiled 2018.05.17 svn.r3504 for Rigaku Oxford Diffraction, GUI svn.r5492)
;
_chemical_formula_moiety         'C9 H13 N O S'
_chemical_formula_sum            'C9 H13 N O S'
_chemical_formula_weight         183.28
_chemical_absolute_configuration ad
_chemical_oxdiff_formula         'C72 H104 N8 O8 S8'
_chemical_oxdiff_usercomment     'from Glebs (EA/Hept)'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.33537 0.55136 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.866900026798
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03377 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      tetragonal
_space_group_IT_number           92
_space_group_name_H-M_alt        'P 41 21 2'
_space_group_name_Hall           ' P 4abw 2nw'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -y+1/2,x+1/2,z+1/4
3 y+1/2,-x+1/2,z+3/4
4 x+1/2,-y+1/2,-z+3/4
5 -x+1/2,y+1/2,-z+1/4
6 -x,-y,z+1/2
7 y,x,-z
8 -y,-x,-z+1/2

_symmetry_Int_Tables_number      92
_cell_length_a                   7.5986(2)
_cell_length_b                   7.5986(2)
_cell_length_c                   34.2923(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1979.99(10)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    14782
_cell_measurement_temperature    140.0(1)
_cell_measurement_theta_max      80.0440
_cell_measurement_theta_min      3.8710
_exptl_absorpt_coefficient_mu    2.532
_exptl_absorpt_correction_T_max  0.92017
_exptl_absorpt_correction_T_min  0.78530
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.2296
_exptl_crystal_F_000             784
_exptl_crystal_colour            Colourless
_exptl_crystal_description       'Block '
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_diffrn_reflns_av_R_equivalents  0.0773
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            16795
_diffrn_reflns_theta_full        82.9480
_diffrn_reflns_theta_max         82.95
_diffrn_reflns_theta_min         5.16
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      140.0(1)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.9828
_diffrn_measured_fraction_theta_max 0.9828
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     88.00 113.00   0.50    0.33    --   49.73  77.00-120.00   50
  2  ω     94.00 173.00   0.50    1.25    --  111.50  77.00-120.00  158
  3  ω    101.00 150.00   0.50    1.25    --  111.50  61.00-150.00   98
  4  ω    145.00 171.00   0.50    1.25    --  111.50  61.00 -30.00   52
  5  ω    129.00 177.00   0.50    1.25    --  111.50  45.00 -90.00   96
  6  ω    104.00 153.00   0.50    1.25    --  111.50  45.00-120.00   98
  7  ω    109.00 134.00   0.50    1.25    --  111.50  30.00-180.00   50
  8  ω    109.00 146.00   0.50    1.25    --  111.50  30.00-150.00   74
  9  ω    122.00 147.00   0.50    1.25    --  111.50  77.00  90.00   50
 10  ω    119.00 177.00   0.50    1.25    --  111.50  61.00 120.00  116
 11  ω    116.00 141.00   0.50    1.25    --  111.50  47.00  84.00   50
 12  ω     65.00  91.00   0.50    1.25    --  111.50 -81.00 164.00   52
 13  ω     42.00  67.00   0.50    1.25    --  111.50-125.00 120.00   50
 14  ω     63.00  97.00   0.50    1.25    --  111.50-102.00  73.00   68
 15  ω     68.00 100.00   0.50    1.25    --  111.50 -94.00 120.00   64
 16  ω     57.00  83.00   0.50    1.25    --  111.50-125.00   0.00   52
 17  ω     59.00 108.00   0.50    1.25    --  111.50-125.00 -30.00   98
 18  ω     42.00  78.00   0.50    1.25    --  111.50-125.00-120.00   72
 19  ω     49.00  88.00   0.50    1.25    --  111.50 -77.00-180.00   78
 20  ω     51.00  76.00   0.50    1.25    --  111.50 -77.00-150.00   50
 21  ω     53.00  89.00   0.50    1.25    --  111.50 -77.00 -90.00   72
 22  ω     62.00  90.00   0.50    1.25    --  111.50 -77.00  60.00   56
 23  ω     43.00  68.00   0.50    1.25    --  111.50 -61.00  90.00   50
 24  ω     52.00  89.00   0.50    1.25    --  111.50 -77.00 150.00   74
 25  ω     41.00  67.00   0.50    1.25    --  111.50 -61.00 150.00   52
 26  ω     46.00  80.00   0.50    1.25    --  111.50 -77.00 120.00   68
 27  ω     43.00  68.00   0.50    1.25    --  111.50 -61.00  60.00   50
 28  ω     41.00  67.00   0.50    1.25    --  111.50 -61.00   0.00   52
 29  ω     95.00 124.00   0.50    1.25    --  111.50 125.00 150.00   58
 30  ω    139.00 176.00   0.50    1.25    --  111.50 125.00 150.00   74
 31  ω    117.00 142.00   0.50    1.25    --  111.50 125.00 -60.00   50
 32  ω    104.00 145.00   0.50    1.25    --  111.50  81.00 -72.00   82
 33  ω    -72.00  19.00   0.50    0.33    --  -49.73  81.00 -72.00  182
 34  ω    -47.00 -21.00   0.50    1.25    --  -90.00  47.00  84.00   52
 35  ω    -20.00  12.00   0.50    0.33    --  -49.73  47.00  84.00   64
 36  ω    -55.00 -20.00   0.50    1.25    --  -90.00  45.00 -90.00   70
 37  ω   -122.00 -96.00   0.50    0.33    --  -49.73 -77.00-180.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku, XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1142791000
_diffrn_orient_matrix_UB_12      0.1220630000
_diffrn_orient_matrix_UB_13      -0.0254112000
_diffrn_orient_matrix_UB_21      -0.1573960000
_diffrn_orient_matrix_UB_22      0.1258647000
_diffrn_orient_matrix_UB_23      -0.0052297000
_diffrn_orient_matrix_UB_31      0.0566967000
_diffrn_orient_matrix_UB_32      0.1023547000
_diffrn_orient_matrix_UB_33      0.0366434000
_diffrn_oxdiff_digest_frames     
;
0158325dc470f7ec0b0c972255d994f445000446997
;
_diffrn_oxdiff_digest_hkl        
;
01c258e5aa9f1bc942c572d04015190a40c29a
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.979
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              6
_reflns_limit_k_min              -6
_reflns_limit_l_max              43
_reflns_limit_l_min              -42
_reflns_number_gt                2128
_reflns_number_total             2170
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.07
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'SIR2011 (Burla et al.,  2007)'
_refine_diff_density_max         0.2700
_refine_diff_density_min         -0.3559
_refine_diff_density_rms         0.0712
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.03(5)
_refine_ls_d_res_high            0.7768
_refine_ls_d_res_low             8.5731
_refine_ls_goodness_of_fit_ref   1.0268
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    20
_refine_ls_number_parameters     115
_refine_ls_number_reflns         2170
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0349
_refine_ls_restrained_S_all      1.0268
_refine_ls_shift/su_max          0.0009
_refine_ls_shift/su_mean         0.0002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0372P)²+0.9086P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0764
_refine_ls_wR_factor_ref         0.0826
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6)
2.c Idealised Me refined as rotating group:
 C8(H8a,H8b,H8c), C9(H9a,H9b,H9c)
;
_atom_sites_solution_primary     direct
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_refinement_flags_posn
S1 S 0.85830(5) 0.61199(6) 0.592026(11) 0.03127(12) Uani 1.000000 .
O1 O 0.89467(19) 0.72034(17) 0.62757(4) 0.0385(3) Uani 1.000000 .
N1 N 0.6466(2) 0.5643(2) 0.58810(4) 0.0313(3) Uani 1.000000 .
H1 H 0.629(3) 0.470(3) 0.6002(6) 0.039(6) Uiso 1.000000 .
C1 C 0.4359(2) 0.7747(2) 0.55821(5) 0.0281(4) Uani 1.000000 .
C2 C 0.4151(2) 0.9556(2) 0.55412(5) 0.0342(4) Uani 1.000000 .
H2 H 0.4535(2) 1.0323(2) 0.57428(5) 0.0410(5) Uiso 1.000000 R
C3 C 0.3386(3) 1.0245(3) 0.52075(6) 0.0430(5) Uani 1.000000 .
H3 H 0.3248(3) 1.1482(3) 0.51824(6) 0.0516(6) Uiso 1.000000 R
C4 C 0.2824(3) 0.9150(3) 0.49111(5) 0.0428(5) Uani 1.000000 .
H4 H 0.2290(3) 0.9628(3) 0.46842(5) 0.0514(6) Uiso 1.000000 R
C5 C 0.3045(3) 0.7348(3) 0.49478(5) 0.0430(5) Uani 1.000000 .
H5 H 0.2684(3) 0.6587(3) 0.47431(5) 0.0516(6) Uiso 1.000000 R
C6 C 0.3793(3) 0.6653(3) 0.52828(5) 0.0369(4) Uani 1.000000 .
H6 H 0.3919(3) 0.5414(3) 0.53080(5) 0.0443(5) Uiso 1.000000 R
C7 C 0.5129(2) 0.7019(2) 0.59578(5) 0.0298(4) Uani 1.000000 .
H7 H 0.5699(2) 0.8004(2) 0.61044(5) 0.0358(4) Uiso 1.000000 R
C8 C 0.3674(3) 0.6228(3) 0.62123(5) 0.0422(4) Uani 1.000000 .
H8a H 0.3189(15) 0.5184(13) 0.6084(2) 0.0632(6) Uiso 1.000000 GR
H8b H 0.4164(5) 0.589(2) 0.64660(18) 0.0632(6) Uiso 1.000000 GR
H8c H 0.2739(10) 0.7099(8) 0.6250(4) 0.0632(6) Uiso 1.000000 GR
C9 C 0.8787(3) 0.7650(3) 0.55258(6) 0.0459(5) Uani 1.000000 .
H9a H 0.8000(17) 0.8651(11) 0.5571(3) 0.0688(7) Uiso 1.000000 GR
H9b H 1.0005(6) 0.8067(18) 0.5510(3) 0.0688(7) Uiso 1.000000 GR
H9c H 0.847(2) 0.7068(7) 0.52808(9) 0.0688(7) Uiso 1.000000 GR


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 1.4967(13) . ?
S1 N1 1.6542(16) . ?
S1 C9 1.7902(19) . ?
N1 C7 1.482(2) . ?
C1 C2 1.390(3) . ?
C1 C6 1.389(2) . ?
C1 C7 1.519(2) . ?
C2 C3 1.386(3) . ?
C3 C4 1.381(3) . ?
C4 C5 1.385(3) . ?
C5 C6 1.386(3) . ?
C7 C8 1.531(2) . ?

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 S1 O1 111.48(8) . . ?
C9 S1 O1 104.02(9) . . ?
C9 S1 N1 99.48(9) . . ?
C7 N1 S1 119.86(12) . . ?
C6 C1 C2 118.79(16) . . ?
C7 C1 C2 119.29(16) . . ?
C7 C1 C6 121.87(16) . . ?
C3 C2 C1 120.30(18) . . ?
C4 C3 C2 120.62(19) . . ?
C5 C4 C3 119.41(18) . . ?
C6 C5 C4 120.10(18) . . ?
C5 C6 C1 120.76(18) . . ?
C1 C7 N1 111.72(13) . . ?
C8 C7 N1 108.61(15) . . ?
C8 C7 C1 110.39(14) . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 5.117
_oxdiff_exptl_absorpt_empirical_full_min 0.581
####################################################################### 
# 
# 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_dm461
_database_code_depnum_ccdc_archive 'CCDC 2374037'
loop_
_audit_author_name
_audit_author_address
'Sergey Belyakov'
;Latvian Institute of Organic Synthesis
Latvia
;
_audit_update_record             
;
2024-07-28 deposited with the CCDC.	2024-11-13 downloaded from the CCDC.
;
_audit_creation_date             2024-02-07
_audit_creation_method           
;
Olex2 1.2-ac4
(compiled 2018.05.17 svn.r3504 for Rigaku Oxford Diffraction, GUI svn.r5492)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H23 N O3 S'
_chemical_formula_sum            'C13 H23 N O3 S'
_chemical_formula_weight         273.38
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c52 h92 n4 o12 s4'
_chemical_oxdiff_usercomment     'from Dz.M.'
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'

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

_cell_length_a                   5.48222(4)
_cell_length_b                   14.93350(11)
_cell_length_c                   17.88217(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1463.990(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    13033
_cell_measurement_temperature    170.0(2)
_cell_measurement_theta_max      79.8390
_cell_measurement_theta_min      3.8620
_shelx_estimated_absorpt_T_max   0.925
_shelx_estimated_absorpt_T_min   0.659
_exptl_absorpt_coefficient_mu    1.978
_exptl_absorpt_correction_T_max  0.90183
_exptl_absorpt_correction_T_min  0.73931
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.93a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       'Needle '
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_av_unetI/netI     0.0169
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            14597
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.052
_diffrn_reflns_theta_min         3.856
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.0(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     48.00  73.00   0.50    0.80    --  111.50-125.00-120.00   50
  2  ω     50.00  97.00   0.50    0.80    --  111.50-125.00-150.00   94
  3  ω     83.00 111.00   0.50    0.80    --  111.50-125.00-120.00   56
  4  ω     46.00  71.00   0.50    0.80    --  111.50 -94.00-120.00   50
  5  ω     78.00 103.00   0.50    0.80    --  111.50 -94.00 -60.00   50
  6  ω     50.00  76.00   0.50    0.80    --  111.50-103.00   8.00   52
  7  ω     59.00  84.00   0.50    0.80    --  111.50 -94.00  90.00   50
  8  ω     52.00  84.00   0.50    0.80    --  111.50-125.00 150.00   64
  9  ω     73.00 104.00   0.50    0.80    --  111.50 -94.00 150.00   62
 10  ω    -20.00  45.00   0.50    0.20    --   49.98 -38.00   0.00  130
 11  ω     42.00  88.00   0.50    0.80    --  111.50 -77.00 -30.00   92
 12  ω     50.00  91.00   0.50    0.80    --  111.50 -77.00   0.00   82
 13  ω     43.00  74.00   0.50    0.80    --  111.50 -77.00  60.00   62
 14  ω     50.00  86.00   0.50    0.80    --  111.50 -77.00  90.00   72
 15  ω     48.00  73.00   0.50    0.80    --  111.50 -77.00 120.00   50
 16  ω     44.00  70.00   0.50    0.80    --  111.50 -77.00 -60.00   52
 17  ω     44.00  69.00   0.50    0.80    --  111.50 -77.00 -90.00   50
 18  ω     45.00  70.00   0.50    0.80    --  111.50 -77.00-150.00   50
 19  ω     41.00  66.00   0.50    0.80    --  111.50 -61.00-120.00   50
 20  ω     41.00  66.00   0.50    0.80    --  111.50 -61.00 -60.00   50
 21  ω     42.00  67.00   0.50    0.80    --  111.50 -61.00 -90.00   50
 22  ω     41.00  66.00   0.50    0.80    --  111.50 -61.00-180.00   50
 23  ω     41.00  66.00   0.50    0.80    --  111.50 -61.00  60.00   50
 24  ω     41.00  66.00   0.50    0.80    --  111.50 -61.00 120.00   50
 25  ω    139.00 165.00   0.50    0.80    --  111.50 117.00-164.00   52
 26  ω     94.00 120.00   0.50    0.20    --   49.98  77.00 -90.00   52
 27  ω    103.00 128.00   0.50    0.80    --  111.50  77.00   0.00   50
 28  ω    143.00 173.00   0.50    0.80    --  111.50  77.00   0.00   60
 29  ω    118.00 175.00   0.50    0.80    --  111.50  45.00 -30.00  114
 30  ω    153.00 178.00   0.50    0.80    --  111.50  45.00  60.00   50
 31  ω    128.00 162.00   0.50    0.80    --  111.50  30.00 120.00   68
 32  ω    103.00 129.00   0.50    0.80    --  111.50  77.00  90.00   52
 33  ω    106.00 132.00   0.50    0.80    --  111.50  45.00  60.00   52
 34  ω    146.00 175.00   0.50    0.80    --  111.50  24.00 -10.00   58
 35  ω    106.00 131.00   0.50    0.80    --  111.50  15.00 -30.00   50
 36  ω    119.00 170.00   0.50    0.80    --  111.50  30.00-120.00  102
 37  ω     -6.00  19.00   0.50    0.20    --  -49.98  19.00 -60.00   50
 38  ω    -41.00 -16.00   0.50    0.80    --  -90.00  24.00 -10.00   50
 39  ω    -77.00 -52.00   0.50    0.80    --  -90.00 117.00-164.00   50
 40  ω   -122.00 -47.00   0.50    0.20    --  -49.98 -24.00-174.00  150
 41  ω   -146.00-121.00   0.50    0.80    --  -90.00 -24.00-174.00   50
 42  ω   -117.00 -92.00   0.50    0.20    --  -49.98 -77.00-180.00   50
 43  ω   -158.00-128.00   0.50    0.80    --  -90.00-103.00   8.00   60
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku, XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0019099000
_diffrn_orient_matrix_UB_12      -0.0901743000
_diffrn_orient_matrix_UB_13      -0.0419036000
_diffrn_orient_matrix_UB_21      0.0884490000
_diffrn_orient_matrix_UB_22      0.0478563000
_diffrn_orient_matrix_UB_23      -0.0713328000
_diffrn_orient_matrix_UB_31      0.2666863000
_diffrn_orient_matrix_UB_32      -0.0150544000
_diffrn_orient_matrix_UB_33      0.0239847000
_diffrn_oxdiff_digest_frames     
;
015ffb5042baf585873556fd5628ed49e3000303fe9
;
_diffrn_oxdiff_digest_hkl        
;
01bf9e4c825b84cf65621b5b7cf6b45071a39b
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.708
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                3141
_reflns_number_total             3179
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.07
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SIR2011 (Burla et al.,  2007)'
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 
;
 Flack x determined using 1297 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.002(4)
_refine_ls_extinction_coef       0.0037(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         3179
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0256
_refine_ls_R_factor_gt           0.0254
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0404P)²+0.3076P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0679
_refine_ls_wR_factor_ref         0.0681
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C6(H6A,H6B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B),
 C13(H13A,H13B), C14(H14A,H14B)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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 0.80219(7) 0.30726(2) 0.61323(2) 0.02134(12) Uani 1 1 d . . . . .
N2 N 0.7986(3) 0.34599(9) 0.69191(7) 0.0232(3) Uani 1 1 d . . . . .
C3 C 0.5691(3) 0.39178(10) 0.71325(9) 0.0203(3) Uani 1 1 d . . . . .
H3 H 0.430(4) 0.3519(13) 0.7051(11) 0.021(5) Uiso 1 1 d . . . . .
C4 C 0.5247(3) 0.47405(11) 0.66222(9) 0.0221(3) Uani 1 1 d . . . . .
H4 H 0.370(4) 0.5028(13) 0.6769(11) 0.019(5) Uiso 1 1 d . . . . .
C5 C 0.4852(3) 0.44350(12) 0.58107(10) 0.0263(3) Uani 1 1 d . . . . .
H5A H 0.459452 0.497106 0.549466 0.032 Uiso 1 1 calc R . . . .
H5B H 0.334544 0.407074 0.578813 0.032 Uiso 1 1 calc R . . . .
C6 C 0.6962(4) 0.38857(12) 0.54795(9) 0.0269(3) Uani 1 1 d . . . . .
H6A H 0.831937 0.429178 0.534367 0.032 Uiso 1 1 calc R . . . .
H6B H 0.640355 0.358105 0.501859 0.032 Uiso 1 1 calc R . . . .
O7 O 1.0410(2) 0.27531(9) 0.58977(7) 0.0308(3) Uani 1 1 d . . . . .
C8 C 0.5983(3) 0.21599(12) 0.60134(10) 0.0291(4) Uani 1 1 d . . . . .
H8A H 0.613173 0.192555 0.550352 0.044 Uiso 1 1 calc GR . . . .
H8B H 0.430702 0.236357 0.609864 0.044 Uiso 1 1 calc GR . . . .
H8C H 0.638627 0.168660 0.637242 0.044 Uiso 1 1 calc GR . . . .
C9 C 0.5725(3) 0.41106(11) 0.79784(9) 0.0222(3) Uani 1 1 d . . . . .
H9 H 0.706269 0.454780 0.808438 0.027 Uiso 1 1 calc R . . . .
C10 C 0.6236(4) 0.32499(12) 0.84156(10) 0.0315(4) Uani 1 1 d . . . . .
H10A H 0.788883 0.303060 0.828816 0.038 Uiso 1 1 calc R . . . .
H10B H 0.504825 0.278509 0.826325 0.038 Uiso 1 1 calc R . . . .
C11 C 0.6067(5) 0.33897(15) 0.92643(10) 0.0405(5) Uani 1 1 d . . . . .
H11A H 0.631893 0.280954 0.952091 0.049 Uiso 1 1 calc R . . . .
H11B H 0.737675 0.380279 0.942659 0.049 Uiso 1 1 calc R . . . .
C12 C 0.3614(5) 0.37724(16) 0.94890(11) 0.0431(5) Uani 1 1 d . . . . .
H12A H 0.358697 0.388171 1.003498 0.052 Uiso 1 1 calc R . . . .
H12B H 0.230802 0.333800 0.936833 0.052 Uiso 1 1 calc R . . . .
C13 C 0.3159(5) 0.46461(14) 0.90740(10) 0.0402(5) Uani 1 1 d . . . . .
H13A H 0.438294 0.509501 0.923305 0.048 Uiso 1 1 calc R . . . .
H13B H 0.152444 0.487743 0.920797 0.048 Uiso 1 1 calc R . . . .
C14 C 0.3307(4) 0.45242(12) 0.82265(9) 0.0305(4) Uani 1 1 d . . . . .
H14A H 0.195021 0.413464 0.806057 0.037 Uiso 1 1 calc R . . . .
H14B H 0.310674 0.511396 0.798128 0.037 Uiso 1 1 calc R . . . .
C15 C 0.7289(3) 0.54151(11) 0.66787(10) 0.0271(4) Uani 1 1 d . . . . .
O16 O 0.7021(3) 0.59531(8) 0.72708(7) 0.0358(3) Uani 1 1 d . . . . .
C17 C 0.8940(4) 0.66020(14) 0.73792(15) 0.0460(5) Uani 1 1 d . . . . .
H17A H 0.901520 0.700190 0.694532 0.069 Uiso 1 1 calc GR . . . .
H17B H 1.050378 0.629112 0.743553 0.069 Uiso 1 1 calc GR . . . .
H17C H 0.860471 0.695351 0.783044 0.069 Uiso 1 1 calc GR . . . .
O18 O 0.9002(3) 0.54780(12) 0.62597(11) 0.0568(5) 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
S1 N2 1.5213(13) . ?
S1 C6 1.7818(17) . ?
S1 O7 1.4553(12) . ?
S1 C8 1.7754(18) . ?
N2 C3 1.482(2) . ?
C3 C4 1.549(2) . ?
C3 C9 1.540(2) . ?
C4 C5 1.537(2) . ?
C4 C15 1.509(2) . ?
C5 C6 1.537(2) . ?
C9 C10 1.530(2) . ?
C9 C14 1.528(2) . ?
C10 C11 1.535(2) . ?
C11 C12 1.515(3) . ?
C12 C13 1.522(3) . ?
C13 C14 1.529(2) . ?
C15 O16 1.337(2) . ?
C15 O18 1.205(2) . ?
O16 C17 1.444(2) . ?

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
N2 S1 C6 110.04(7) . . ?
N2 S1 C8 113.23(9) . . ?
O7 S1 N2 113.77(8) . . ?
O7 S1 C6 109.14(9) . . ?
O7 S1 C8 106.26(9) . . ?
C8 S1 C6 103.86(9) . . ?
C3 N2 S1 115.12(11) . . ?
N2 C3 C4 110.32(13) . . ?
N2 C3 C9 109.19(12) . . ?
C9 C3 C4 115.60(13) . . ?
C5 C4 C3 110.05(13) . . ?
C15 C4 C3 111.93(13) . . ?
C15 C4 C5 111.46(14) . . ?
C4 C5 C6 114.61(14) . . ?
C5 C6 S1 110.89(11) . . ?
C10 C9 C3 110.31(13) . . ?
C14 C9 C3 110.50(13) . . ?
C14 C9 C10 110.49(15) . . ?
C9 C10 C11 112.33(15) . . ?
C12 C11 C10 111.53(17) . . ?
C11 C12 C13 109.85(18) . . ?
C12 C13 C14 111.88(16) . . ?
C9 C14 C13 112.46(16) . . ?
O16 C15 C4 111.87(15) . . ?
O18 C15 C4 126.04(16) . . ?
O18 C15 O16 122.09(17) . . ?
C15 O16 C17 115.44(16) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.360
_oxdiff_exptl_absorpt_empirical_full_min 0.687
####################################################################### 
# 
# 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_glebstol
_database_code_depnum_ccdc_archive 'CCDC 2374039'
loop_
_audit_author_name
_audit_author_address
'Sergey Belyakov'
;Latvian Institute of Organic Synthesis
Latvia
;
_audit_update_record             
;
2024-07-28 deposited with the CCDC.	2024-11-13 downloaded from the CCDC.
;
_audit_creation_date             2023-06-13
_audit_creation_method           
;
Olex2 1.2-ac4
(compiled 2018.05.17 svn.r3504 for Rigaku Oxford Diffraction, GUI svn.r5492)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H20 N2 O S'
_chemical_formula_sum            'C14 H20 N2 O S'
_chemical_formula_weight         264.38
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C56 H80 N8 O4 S4'
_chemical_oxdiff_usercomment     'from Glebs'
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'

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

_cell_length_a                   6.1844(2)
_cell_length_b                   8.2409(2)
_cell_length_c                   28.5035(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1452.68(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10153
_cell_measurement_temperature    140.0(1)
_cell_measurement_theta_max      79.9770
_cell_measurement_theta_min      3.1150
_exptl_absorpt_coefficient_mu    1.898
_exptl_absorpt_correction_T_max  0.94016
_exptl_absorpt_correction_T_min  0.86041
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.209
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       'Parallelepiped '
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0754
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            12582
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         88.010
_diffrn_reflns_theta_min         3.101
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      140.0(1)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     98.00 153.00   0.50    0.80    --  111.50  61.00  60.00  110
  2  ω    126.00 151.00   0.50    0.80    --  111.50  26.00  94.00   50
  3  ω    153.00 178.00   0.50    0.80    --  111.50  15.00   0.00   50
  4  ω     93.00 177.00   0.50    0.80    --  111.50  77.00-120.00  168
  5  ω    -37.00  24.00   0.50    0.20    --  -49.73  26.00  94.00  122
  6  ω   -154.00-100.00   0.50    0.80    --  -90.00-109.00  93.00  108
  7  ω   -112.00 -82.00   0.50    0.20    --  -49.73-125.00-150.00   60
  8  ω   -147.00-121.00   0.50    0.80    --  -90.00-105.00-175.00   52
  9  ω   -117.00 -90.00   0.50    0.20    --  -49.73 -77.00-180.00   54
 10  ω   -120.00 -95.00   0.50    0.20    --  -49.73 -77.00-150.00   50
 11  ω    -75.00  -9.00   0.50    0.20    --  -49.73 105.00 -75.00  132
 12  ω     46.00  84.00   0.50    0.80    --  111.50 -94.00-150.00   76
 13  ω     74.00 106.00   0.50    0.80    --  111.50-125.00-180.00   64
 14  ω     84.00 109.00   0.50    0.80    --  111.50-125.00-120.00   50
 15  ω     41.00 106.00   0.50    0.80    --  111.50-105.00-175.00  130
 16  ω     45.00  71.00   0.50    0.80    --  111.50-125.00  60.00   52
 17  ω     52.00  80.00   0.50    0.80    --  111.50-109.00  93.00   56
 18  ω     69.00 101.00   0.50    0.80    --  111.50 -94.00 150.00   64
 19  ω     77.00 105.00   0.50    0.80    --  111.50-125.00 120.00   56
 20  ω     41.00  85.00   0.50    0.80    --  111.50 -94.00-120.00   88
 21  ω     41.00  66.00   0.50    0.80    --  111.50 -77.00-180.00   50
 22  ω     41.00  81.00   0.50    0.80    --  111.50 -77.00 -60.00   80
 23  ω     55.00  91.00   0.50    0.80    --  111.50 -77.00 -30.00   72
 24  ω     41.00  68.00   0.50    0.80    --  111.50 -61.00 -60.00   54
 25  ω     56.00  90.00   0.50    0.80    --  111.50 -77.00   0.00   68
 26  ω     46.00  83.00   0.50    0.80    --  111.50 -77.00  30.00   74
 27  ω     42.00  84.00   0.50    0.80    --  111.50 -77.00  90.00   84
 28  ω     41.00  66.00   0.50    0.80    --  111.50 -61.00 120.00   50
 29  ω     41.00  67.00   0.50    0.80    --  111.50 -61.00  30.00   52
 30  ω     41.00  67.00   0.50    0.80    --  111.50 -61.00 -90.00   52
 31  ω     97.00 136.00   0.50    0.80    --  111.50 125.00-120.00   78
 32  ω    116.00 177.00   0.50    0.80    --  111.50 125.00 -60.00  122
 33  ω    142.00 167.00   0.50    0.80    --  111.50 125.00-120.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku, XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1892566000
_diffrn_orient_matrix_UB_12      0.1039793000
_diffrn_orient_matrix_UB_13      -0.0182742000
_diffrn_orient_matrix_UB_21      -0.1526592000
_diffrn_orient_matrix_UB_22      0.1469339000
_diffrn_orient_matrix_UB_23      -0.0045755000
_diffrn_orient_matrix_UB_31      0.0541209000
_diffrn_orient_matrix_UB_32      0.0505205000
_diffrn_orient_matrix_UB_33      0.0506572000
_diffrn_oxdiff_digest_frames     
;
0165ce04a169302b1386997101a520b7c6000306c19
;
_diffrn_oxdiff_digest_hkl        
;
01accd986190f94f42455f11d84bba5c950183
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.690
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.939
_reflns_number_gt                3051
_reflns_number_total             3152
_reflns_odcompleteness_completeness 99.58
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.07
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.395
_refine_diff_density_min         -0.814
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details 
;
 Flack x determined using 1186 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.006(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.179
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     171
_refine_ls_number_reflns         3152
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0421
_refine_ls_restrained_S_all      1.179
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0291P)²+1.2988P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1034
_refine_ls_wR_factor_ref         0.1095
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C9(H9)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C12(H12A,H12B,H12C), C14(H14A,H14B,H14C), C13(H13A,H13B,
 H13C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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 0.36021(12) 0.52700(9) 0.63208(3) 0.02503(19) Uani 1 1 d . . . . .
O1 O 0.1612(4) 0.5663(3) 0.60685(9) 0.0337(6) Uani 1 1 d . . . . .
N1 N 0.7822(6) 0.0224(4) 0.66532(13) 0.0440(8) Uani 1 1 d . . . . .
N2 N 0.4538(5) 0.3564(3) 0.63035(11) 0.0293(6) Uani 1 1 d . . . . .
C1 C 0.7872(5) 0.1222(4) 0.63749(14) 0.0311(7) Uani 1 1 d . . . . .
C2 C 0.7925(5) 0.2473(4) 0.60106(13) 0.0301(7) Uani 1 1 d . . . . .
H2A H 0.867496 0.204585 0.572968 0.036 Uiso 1 1 calc R . . . .
H2B H 0.874597 0.342445 0.612590 0.036 Uiso 1 1 calc R . . . .
C3 C 0.5609(5) 0.3004(4) 0.58757(12) 0.0260(7) Uani 1 1 d . . . . .
H3 H 0.576(6) 0.393(4) 0.5638(12) 0.016(8) Uiso 1 1 d . . . . .
C4 C 0.4438(5) 0.1605(4) 0.56398(12) 0.0228(6) Uani 1 1 d . . . . .
C5 C 0.5056(5) 0.1141(4) 0.51864(13) 0.0279(7) Uani 1 1 d . . . . .
H5 H 0.615184 0.173305 0.502754 0.033 Uiso 1 1 calc R . . . .
C6 C 0.4086(6) -0.0174(4) 0.49664(13) 0.0317(7) Uani 1 1 d . . . . .
H6 H 0.452668 -0.048808 0.466029 0.038 Uiso 1 1 calc R . . . .
C7 C 0.2466(6) -0.1029(4) 0.51973(14) 0.0323(8) Uani 1 1 d . . . . .
H7 H 0.179042 -0.192669 0.504813 0.039 Uiso 1 1 calc R . . . .
C8 C 0.1838(6) -0.0573(4) 0.56442(13) 0.0311(7) Uani 1 1 d . . . . .
H8 H 0.072956 -0.115811 0.580109 0.037 Uiso 1 1 calc R . . . .
C9 C 0.2824(5) 0.0737(4) 0.58646(13) 0.0271(7) Uani 1 1 d . . . . .
H9 H 0.238643 0.104065 0.617187 0.033 Uiso 1 1 calc R . . . .
C10 C 0.5547(6) 0.6745(4) 0.61366(14) 0.0330(8) Uani 1 1 d . . . . .
H10A H 0.563656 0.674932 0.579332 0.050 Uiso 1 1 calc GR . . . .
H10B H 0.696479 0.647305 0.626850 0.050 Uiso 1 1 calc GR . . . .
H10C H 0.510537 0.782155 0.624702 0.050 Uiso 1 1 calc GR . . . .
C11 C 0.3150(5) 0.5626(4) 0.69413(14) 0.0315(8) Uani 1 1 d . . . . .
C12 C 0.5293(6) 0.5536(6) 0.72085(15) 0.0439(10) Uani 1 1 d . . . . .
H12A H 0.597584 0.448191 0.715120 0.066 Uiso 1 1 calc GR . . . .
H12B H 0.502013 0.566499 0.754520 0.066 Uiso 1 1 calc GR . . . .
H12C H 0.625392 0.640460 0.710040 0.066 Uiso 1 1 calc GR . . . .
C14 C 0.1614(7) 0.4286(5) 0.71078(14) 0.0398(9) Uani 1 1 d . . . . .
H14A H 0.025346 0.435495 0.693273 0.060 Uiso 1 1 calc GR . . . .
H14B H 0.132440 0.442255 0.744347 0.060 Uiso 1 1 calc GR . . . .
H14C H 0.228258 0.322458 0.705354 0.060 Uiso 1 1 calc GR . . . .
C13 C 0.2097(7) 0.7286(5) 0.69984(16) 0.0448(10) Uani 1 1 d . . . . .
H13A H 0.310926 0.813125 0.689728 0.067 Uiso 1 1 calc GR . . . .
H13B H 0.171835 0.745637 0.732865 0.067 Uiso 1 1 calc GR . . . .
H13C H 0.078506 0.733785 0.680611 0.067 Uiso 1 1 calc GR . . . .


_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 1.462(3) . ?
S1 N2 1.521(3) . ?
S1 C10 1.789(4) . ?
S1 C11 1.814(4) . ?
N1 C1 1.143(5) . ?
N2 C3 1.462(4) . ?
C1 C2 1.464(5) . ?
C2 C3 1.546(5) . ?
C3 C4 1.519(5) . ?
C4 C5 1.401(5) . ?
C4 C9 1.385(5) . ?
C5 C6 1.388(5) . ?
C6 C7 1.390(5) . ?
C7 C8 1.384(5) . ?
C8 C9 1.390(5) . ?
C11 C12 1.530(5) . ?
C11 C14 1.532(5) . ?
C11 C13 1.524(5) . ?

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 N2 120.61(16) . . ?
O1 S1 C10 105.73(17) . . ?
O1 S1 C11 108.29(15) . . ?
N2 S1 C10 111.26(17) . . ?
N2 S1 C11 103.88(16) . . ?
C10 S1 C11 106.24(17) . . ?
C3 N2 S1 119.4(2) . . ?
N1 C1 C2 178.7(4) . . ?
C1 C2 C3 110.8(3) . . ?
N2 C3 C2 107.5(3) . . ?
N2 C3 C4 113.1(3) . . ?
C4 C3 C2 109.7(3) . . ?
C5 C4 C3 119.1(3) . . ?
C9 C4 C3 122.0(3) . . ?
C9 C4 C5 118.9(3) . . ?
C6 C5 C4 120.8(3) . . ?
C5 C6 C7 119.6(3) . . ?
C8 C7 C6 120.0(3) . . ?
C7 C8 C9 120.3(3) . . ?
C4 C9 C8 120.5(3) . . ?
C12 C11 S1 110.1(3) . . ?
C12 C11 C14 110.4(3) . . ?
C14 C11 S1 106.3(2) . . ?
C13 C11 S1 108.4(3) . . ?
C13 C11 C12 111.1(3) . . ?
C13 C11 C14 110.4(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
S1 N2 C3 C2 123.5(3) . . . . ?
S1 N2 C3 C4 -115.3(3) . . . . ?
O1 S1 N2 C3 73.8(3) . . . . ?
O1 S1 C11 C12 -169.6(3) . . . . ?
O1 S1 C11 C14 70.9(3) . . . . ?
O1 S1 C11 C13 -47.8(3) . . . . ?
N2 S1 C11 C12 61.1(3) . . . . ?
N2 S1 C11 C14 -58.5(3) . . . . ?
N2 S1 C11 C13 -177.1(3) . . . . ?
N2 C3 C4 C5 168.7(3) . . . . ?
N2 C3 C4 C9 -13.5(4) . . . . ?
C1 C2 C3 N2 56.9(4) . . . . ?
C1 C2 C3 C4 -66.5(4) . . . . ?
C2 C3 C4 C5 -71.3(4) . . . . ?
C2 C3 C4 C9 106.6(3) . . . . ?
C3 C4 C5 C6 177.3(3) . . . . ?
C3 C4 C9 C8 -177.7(3) . . . . ?
C4 C5 C6 C7 0.7(5) . . . . ?
C5 C4 C9 C8 0.1(5) . . . . ?
C5 C6 C7 C8 -0.3(5) . . . . ?
C6 C7 C8 C9 -0.1(5) . . . . ?
C7 C8 C9 C4 0.2(5) . . . . ?
C9 C4 C5 C6 -0.6(5) . . . . ?
C10 S1 N2 C3 -50.8(3) . . . . ?
C10 S1 C11 C12 -56.4(3) . . . . ?
C10 S1 C11 C14 -175.9(2) . . . . ?
C10 S1 C11 C13 65.4(3) . . . . ?
C11 S1 N2 C3 -164.7(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 4.154
_oxdiff_exptl_absorpt_empirical_full_min 0.381
####################################################################### 
# 
# 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_GlebPav
_database_code_depnum_ccdc_archive 'CCDC 2374038'
loop_
_audit_author_name
_audit_author_address
'Sergey Belyakov'
;Latvian Institute of Organic Synthesis
Latvia
;
_audit_update_record             
;
2024-07-28 deposited with the CCDC.	2024-11-13 downloaded from the CCDC.
;
_audit_creation_date             2024-05-15
_audit_creation_method           
;
Olex2 1.2-ac4
(compiled 2018.05.17 svn.r3504 for Rigaku Oxford Diffraction, GUI svn.r5492)
;
_chemical_formula_moiety         'C12 H18 Li N O S'
_chemical_formula_sum            'C12 H18 Li N O S'
_chemical_formula_weight         231.29
_chemical_absolute_configuration ad
_chemical_oxdiff_formula         'C26 H20 Li2 O10'
_chemical_oxdiff_usercomment     'from G.J. '
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03377 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Li 0.00116 0.00033 1.12820 0.75080 0.61750 0.46530 3.95460 1.05240 85.39050
168.26100 0.0377000011504
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.33537 0.55136 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.866900026798
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           ' P 2yb'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z

_symmetry_Int_Tables_number      4
_cell_length_a                   8.4381(3)
_cell_length_b                   5.4756(2)
_cell_length_c                   13.8664(5)
_cell_angle_alpha                90
_cell_angle_beta                 103.119(4)
_cell_angle_gamma                90
_cell_volume                     623.96(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3807
_cell_measurement_temperature    155.0(1)
_cell_measurement_theta_max      78.4330
_cell_measurement_theta_min      3.2720
_exptl_absorpt_coefficient_mu    2.098
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
;
_exptl_crystal_density_diffrn    1.2310
_exptl_crystal_F_000             248
_exptl_crystal_colour            'Colourless '
_exptl_crystal_description       Plate
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.01
_diffrn_reflns_av_R_equivalents  0.0468
_diffrn_reflns_av_unetI/netI     0.0541
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5357
_diffrn_reflns_theta_full        70.0
_diffrn_reflns_theta_max         80.19
_diffrn_reflns_theta_min         3.27
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      155.0(1)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.98
_diffrn_measured_fraction_theta_max 0.7884
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     44.00  70.00   0.50    1.00    --  113.25-125.00  90.00   52
  2  ω     79.00 105.00   0.50    1.00    --  113.25-125.00  90.00   52
  3  ω     47.00  97.00   0.50    1.00    --  113.25 -94.00-120.00  100
  4  ω     42.00  80.00   0.50    1.00    --  113.25 -94.00 -30.00   76
  5  ω     46.00  91.00   0.50    1.00    --  113.25 -77.00   0.00   90
  6  ω     48.00  92.00   0.50    1.00    --  113.25 -77.00 -30.00   88
  7  ω     66.00  91.00   0.50    1.00    --  113.25 -77.00  90.00   50
  8  ω     42.00  67.00   0.50    1.00    --  113.25 -61.00  90.00   50
  9  ω     44.00  73.00   0.50    1.00    --  113.25 -77.00 -60.00   58
 10  ω     59.00  86.00   0.50    1.00    --  113.25 -77.00 -90.00   54
 11  ω     48.00  91.00   0.50    1.00    --  113.25 -77.00-180.00   86
 12  ω     42.00  67.00   0.50    1.00    --  113.25 -61.00-180.00   50
 13  ω     42.00  67.00   0.50    1.00    --  113.25 -61.00-120.00   50
 14  ω     42.00  67.00   0.50    1.00    --  113.25 -61.00   0.00   50
 15  ω     42.00  67.00   0.50    1.00    --  113.25 -61.00 150.00   50
 16  ω    -18.00   7.00   0.50    0.25    --   47.39 -26.00  74.00   50
 17  ω     89.00 119.00   0.50    0.25    --   47.39  77.00 150.00   60
 18  ω    115.00 153.00   0.50    1.00    --  113.25  77.00 120.00   76
 19  ω    149.00 174.00   0.50    1.00    --  113.25  77.00 -30.00   50
 20  ω    153.00 178.00   0.50    1.00    --  113.25  61.00 -90.00   50
 21  ω    102.00 134.00   0.50    1.00    --  113.25  61.00 -90.00   64
 22  ω    103.00 178.00   0.50    1.00    --  113.25  26.00-121.00  150
 23  ω    104.00 157.00   0.50    1.00    --  113.25  30.00 -60.00  106
 24  ω    103.00 132.00   0.50    1.00    --  113.25  45.00   0.00   58
 25  ω    108.00 175.00   0.50    1.00    --  113.25  45.00 -30.00  134
 26  ω     79.00 107.00   0.50    0.25    --   47.39  26.00-121.00   56
 27  ω    -41.00  24.00   0.50    0.25    --  -47.39  19.00   0.00  130
 28  ω    -39.00  26.00   0.50    0.25    --  -47.39  26.00-121.00  130
 29  ω    -42.00 -17.00   0.50    1.00    --  -91.75  26.00-121.00   50
 30  ω    -44.00 -18.00   0.50    1.00    --  -91.75  30.00-180.00   52
 31  ω    -66.00 -23.00   0.50    1.00    --  -91.75 125.00 -60.00   86
 32  ω   -134.00 -84.00   0.50    1.00    --  -91.75 -26.00  74.00  100
 33  ω   -121.00 -75.00   0.50    0.25    --  -47.39 -26.00  74.00   92
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku, XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0688708000
_diffrn_orient_matrix_UB_12      -0.0871990000
_diffrn_orient_matrix_UB_13      0.1069299000
_diffrn_orient_matrix_UB_21      -0.1680439000
_diffrn_orient_matrix_UB_22      0.0376654000
_diffrn_orient_matrix_UB_23      0.0238066000
_diffrn_orient_matrix_UB_31      -0.0462510000
_diffrn_orient_matrix_UB_32      -0.2649175000
_diffrn_orient_matrix_UB_33      -0.0317512000
_diffrn_oxdiff_digest_frames     
;
01f449467be9eeacaca68f11483b269c87000338f73
;
_diffrn_oxdiff_digest_hkl        
;
01d5450539a207076dc5431df8fade302338bd
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.531
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              5
_reflns_limit_k_min              -6
_reflns_limit_l_max              17
_reflns_limit_l_min              -17
_reflns_number_gt                2018
_reflns_number_total             2142
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.4927
_refine_diff_density_min         -0.2044
_refine_diff_density_rms         0.0524
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.02(3)
_refine_ls_d_res_high            0.7824
_refine_ls_d_res_low             13.5045
_refine_ls_goodness_of_fit_ref   1.0505
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    26
_refine_ls_number_parameters     153
_refine_ls_number_reflns         2142
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0426
_refine_ls_restrained_S_all      1.0505
_refine_ls_shift/su_max          0.0027
_refine_ls_shift/su_mean         0.0005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0654P)²+0.1427P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1096
_refine_ls_wR_factor_ref         0.1131
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C8(H8)
2.b Idealised Me refined as rotating group:
 C2(H2a,H2b,H2c), C10(H10a,H10b,H10c), C11(H11a,H11b,H11c), C12(H12a,H12b,H12c)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
S1 S 0.48308(6) 0.67084(13) 0.66600(4) 0.02570(17) Uani 1.000000 .
O1 O 0.4665(2) 0.8097(3) 0.56635(13) 0.0289(4) Uani 1.000000 .
N1 N 0.5727(3) 0.4149(4) 0.66257(15) 0.0272(4) Uani 1.000000 .
C1 C 0.7412(3) 0.4179(5) 0.7245(2) 0.0302(5) Uani 1.000000 .
H1 H 0.805(4) 0.558(7) 0.710(2) 0.032(8) Uiso 1.000000 .
C2 C 0.8249(3) 0.1879(7) 0.6984(2) 0.0386(6) Uani 1.000000 .
H2a H 0.9349(12) 0.177(3) 0.7406(13) 0.0579(9) Uiso 1.000000 GR
H2b H 0.7621(17) 0.0438(8) 0.7090(18) 0.0579(9) Uiso 1.000000 GR
H2c H 0.831(3) 0.195(2) 0.6288(6) 0.0579(9) Uiso 1.000000 GR
C3 C 0.7481(3) 0.4285(5) 0.83460(19) 0.0312(5) Uani 1.000000 .
C4 C 0.6723(4) 0.2497(6) 0.8800(2) 0.0383(7) Uani 1.000000 .
H4 H 0.6164(4) 0.1194(6) 0.8414(2) 0.0460(8) Uiso 1.000000 R
C5 C 0.6772(4) 0.2593(7) 0.9803(2) 0.0481(8) Uani 1.000000 .
H5 H 0.6241(4) 0.1371(7) 1.0101(2) 0.0577(10) Uiso 1.000000 R
C6 C 0.7601(5) 0.4488(8) 1.0376(2) 0.0547(9) Uani 1.000000 .
H6 H 0.7638(5) 0.4561(8) 1.1065(2) 0.0657(11) Uiso 1.000000 R
C7 C 0.8371(5) 0.6265(7) 0.9936(2) 0.0535(9) Uani 1.000000 .
H7 H 0.8939(5) 0.7558(7) 1.0323(2) 0.0642(11) Uiso 1.000000 R
C8 C 0.8310(4) 0.6148(6) 0.8928(2) 0.0430(7) Uani 1.000000 .
H8 H 0.8844(4) 0.7367(6) 0.8631(2) 0.0516(9) Uiso 1.000000 R
C9 C 0.2719(3) 0.5706(6) 0.6607(2) 0.0331(6) Uani 1.000000 .
C10 C 0.1634(4) 0.7925(7) 0.6473(3) 0.0482(8) Uani 1.000000 .
H10a H 0.207(2) 0.912(2) 0.6993(13) 0.0723(12) Uiso 1.000000 GR
H10b H 0.160(3) 0.865(3) 0.5823(9) 0.0723(12) Uiso 1.000000 GR
H10c H 0.0534(9) 0.7444(11) 0.652(2) 0.0723(12) Uiso 1.000000 GR
C11 C 0.2147(4) 0.3923(6) 0.5753(2) 0.0370(6) Uani 1.000000 .
H11a H 0.227(3) 0.4677(18) 0.5133(3) 0.0555(10) Uiso 1.000000 GR
H11b H 0.280(2) 0.2432(19) 0.5875(9) 0.0555(10) Uiso 1.000000 GR
H11c H 0.1001(9) 0.352(4) 0.5704(12) 0.0555(10) Uiso 1.000000 GR
C12 C 0.2777(4) 0.4490(7) 0.7602(2) 0.0435(7) Uani 1.000000 .
H12a H 0.336(3) 0.293(3) 0.7634(9) 0.0653(11) Uiso 1.000000 GR
H12b H 0.334(3) 0.556(2) 0.8137(2) 0.0653(11) Uiso 1.000000 GR
H12c H 0.1666(4) 0.420(5) 0.7677(10) 0.0653(11) Uiso 1.000000 GR
Li1 Li 0.4823(5) 0.6566(11) 0.4442(3) 0.0306(8) Uani 1.000000 .


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 1.5553(18) . ?
S1 N1 1.599(2) . ?
S1 C9 1.850(3) . ?
O1 Li1 1.922(5) . ?
O1 Li1 1.961(6) 2_656 ?
N1 C1 1.484(3) . ?
N1 Li1 2.023(6) 2_646 ?
C1 C2 1.527(4) . ?
C1 C3 1.516(4) . ?
C3 C4 1.395(4) . ?
C3 C8 1.388(4) . ?
C4 C5 1.383(4) . ?
C5 C6 1.395(6) . ?
C6 C7 1.385(6) . ?
C7 C8 1.389(4) . ?
C9 C10 1.507(5) . ?
C9 C11 1.525(4) . ?
C9 C12 1.524(4) . ?

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 S1 O1 110.48(11) . . ?
C9 S1 O1 102.58(11) . . ?
C9 S1 N1 101.35(13) . . ?
Li1 O1 S1 124.0(2) . . ?
Li1 O1 S1 124.25(15) 2_656 . ?
C1 N1 S1 111.73(18) . . ?
Li1 N1 S1 127.09(17) 2_646 . ?
Li1 N1 C1 117.5(2) 2_646 . ?
C2 C1 N1 106.7(2) . . ?
C3 C1 N1 113.3(2) . . ?
C3 C1 C2 110.8(2) . . ?
C4 C3 C1 120.7(3) . . ?
C8 C3 C1 120.8(3) . . ?
C8 C3 C4 118.4(3) . . ?
C5 C4 C3 121.0(3) . . ?
C6 C5 C4 119.8(3) . . ?
C7 C6 C5 119.8(3) . . ?
C8 C7 C6 119.8(3) . . ?
C7 C8 C3 121.2(3) . . ?
C10 C9 S1 108.6(2) . . ?
C11 C9 S1 110.7(2) . . ?
C11 C9 C10 110.1(3) . . ?
C12 C9 S1 105.1(2) . . ?
C12 C9 C10 110.9(3) . . ?
C12 C9 C11 111.3(3) . . ?
N1 Li1 O1 106.8(3) 2_656 . ?
N1 Li1 O1 129.8(2) 2_656 2_646 ?


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.510
_oxdiff_exptl_absorpt_empirical_full_min 0.791
####################################################################### 
# 
# 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_GJ1300
_database_code_depnum_ccdc_archive 'CCDC 2374036'
loop_
_audit_author_name
_audit_author_address
'Sergey Belyakov'
;Latvian Institute of Organic Synthesis
Latvia
;
_audit_update_record             
;
2024-07-28 deposited with the CCDC.	2024-11-13 downloaded from the CCDC.
;
_audit_creation_date             2024-01-18
_audit_creation_method           
;
Olex2 1.2-ac4
(compiled 2018.05.17 svn.r3504 for Rigaku Oxford Diffraction, GUI svn.r5492)
;
_chemical_formula_moiety         'C10 H13 N O S'
_chemical_formula_sum            'C10 H13 N O S'
_chemical_formula_weight         195.29
_chemical_absolute_configuration ad
_chemical_oxdiff_formula         'c20 h26 n2 o2 s2'
_chemical_oxdiff_usercomment     GJ-1300
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.33537 0.55136 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.866900026798
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03377 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           ' P 2yb'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z

_symmetry_Int_Tables_number      4
_cell_length_a                   6.73890(7)
_cell_length_b                   6.34305(6)
_cell_length_c                   12.08776(13)
_cell_angle_alpha                90
_cell_angle_beta                 100.7244(10)
_cell_angle_gamma                90
_cell_volume                     507.668(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6919
_cell_measurement_temperature    160.0(3)
_cell_measurement_theta_max      78.8260
_cell_measurement_theta_min      3.7190
_exptl_absorpt_coefficient_mu    2.504
_exptl_absorpt_correction_T_max  0.94017
_exptl_absorpt_correction_T_min  0.70554
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.93a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.2774
_exptl_crystal_F_000             208
_exptl_crystal_description       Prism
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.04
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_av_unetI/netI     0.0169
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7674
_diffrn_reflns_theta_full        80.0
_diffrn_reflns_theta_max         80.19
_diffrn_reflns_theta_min         3.72
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      160.0(3)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.9824
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -17.00  36.00   0.50    0.20    --   49.73 -19.00 -30.00  106
  2  ω    -10.00  15.00   0.50    0.20    --   49.73 -76.00 -25.00   50
  3  ω     32.00  58.00   0.50    0.20    --   49.73 -76.00 -25.00   52
  4  ω     44.00  69.00   0.50    0.75    --  111.50-125.00 -60.00   50
  5  ω     86.00 111.00   0.50    0.75    --  111.50-125.00 -60.00   50
  6  ω     80.00 105.00   0.50    0.75    --  111.50 -94.00 -30.00   50
  7  ω     41.00  67.00   0.50    0.75    --  111.50 -94.00  30.00   52
  8  ω     86.00 111.00   0.50    0.75    --  111.50-125.00  60.00   50
  9  ω     43.00 111.00   0.50    0.75    --  111.50-125.00  90.00  136
 10  ω     58.00  95.00   0.50    0.75    --  111.50-125.00 150.00   74
 11  ω     43.00  68.00   0.50    0.75    --  111.50 -61.00 120.00   50
 12  ω     47.00  80.00   0.50    0.75    --  111.50 -77.00  30.00   66
 13  ω     51.00  76.00   0.50    0.75    --  111.50 -77.00 -30.00   50
 14  ω     41.00  66.00   0.50    0.75    --  111.50 -77.00   0.00   50
 15  ω     61.00  86.00   0.50    0.75    --  111.50 -77.00  60.00   50
 16  ω     46.00  71.00   0.50    0.75    --  111.50 -77.00 120.00   50
 17  ω     53.00  92.00   0.50    0.75    --  111.50 -77.00 -60.00   78
 18  ω     41.00  66.00   0.50    0.75    --  111.50 -76.00 -25.00   50
 19  ω     43.00  91.00   0.50    0.75    --  111.50 -77.00-120.00   96
 20  ω     41.00  66.00   0.50    0.75    --  111.50 -61.00-180.00   50
 21  ω     44.00  69.00   0.50    0.75    --  111.50 -77.00-150.00   50
 22  ω     41.00  66.00   0.50    0.75    --  111.50 -61.00-120.00   50
 23  ω     42.00  67.00   0.50    0.75    --  111.50 -61.00 -90.00   50
 24  ω     41.00  66.00   0.50    0.75    --  111.50 -61.00 -30.00   50
 25  ω     41.00  66.00   0.50    0.75    --  111.50 -61.00   0.00   50
 26  ω     41.00  66.00   0.50    0.75    --  111.50 -61.00  60.00   50
 27  ω    106.00 131.00   0.50    0.75    --  111.50  15.00-120.00   50
 28  ω     89.00 118.00   0.50    0.20    --   49.73  77.00-180.00   58
 29  ω     92.00 126.00   0.50    0.75    --  111.50  77.00  60.00   68
 30  ω     94.00 120.00   0.50    0.75    --  111.50  77.00  30.00   52
 31  ω    128.00 154.00   0.50    0.75    --  111.50  77.00  30.00   52
 32  ω    149.00 175.00   0.50    0.75    --  111.50  77.00  60.00   52
 33  ω    135.00 160.00   0.50    0.75    --  111.50  77.00 120.00   50
 34  ω     93.00 169.00   0.50    0.75    --  111.50  76.00 101.00  152
 35  ω     93.00 118.00   0.50    0.75    --  111.50  77.00 120.00   50
 36  ω     94.00 119.00   0.50    0.75    --  111.50  77.00 150.00   50
 37  ω     52.00  77.00   0.50    0.20    --   49.73  76.00 101.00   50
 38  ω     99.00 126.00   0.50    0.75    --  111.50  61.00  30.00   54
 39  ω    145.00 173.00   0.50    0.75    --  111.50  61.00  30.00   56
 40  ω    137.00 174.00   0.50    0.75    --  111.50  45.00  60.00   74
 41  ω    101.00 134.00   0.50    0.75    --  111.50  58.00  40.80   66
 42  ω    110.00 136.00   0.50    0.75    --  111.50  45.00   0.00   52
 43  ω    153.00 178.00   0.50    0.75    --  111.50  45.00   0.00   50
 44  ω    102.00 132.00   0.50    0.75    --  111.50  45.00  90.00   60
 45  ω    101.00 140.00   0.50    0.75    --  111.50  61.00-120.00   78
 46  ω     97.00 127.00   0.50    0.75    --  111.50  61.00-150.00   60
 47  ω    142.00 171.00   0.50    0.75    --  111.50  61.00-150.00   58
 48  ω    143.00 177.00   0.50    0.75    --  111.50  45.00-120.00   68
 49  ω    133.00 160.00   0.50    0.75    --  111.50  30.00-180.00   54
 50  ω    135.00 161.00   0.50    0.75    --  111.50  30.00-150.00   52
 51  ω    102.00 136.00   0.50    0.75    --  111.50  45.00-120.00   68
 52  ω    105.00 133.00   0.50    0.75    --  111.50  30.00-150.00   56
 53  ω    109.00 152.00   0.50    0.75    --  111.50  15.00-180.00   86
 54  ω    146.00 171.00   0.50    0.75    --  111.50  45.00 -60.00   50
 55  ω    119.00 162.00   0.50    0.75    --  111.50  30.00  30.00   86
 56  ω    112.00 157.00   0.50    0.75    --  111.50  15.00  30.00   90
 57  ω    153.00 178.00   0.50    0.75    --  111.50  45.00  90.00   50
 58  ω    153.00 178.00   0.50    0.75    --  111.50 125.00 120.00   50
 59  ω     97.00 130.00   0.50    0.75    --  111.50 125.00 120.00   66
 60  ω    111.00 137.00   0.50    0.75    --  111.50 125.00-150.00   52
 61  ω    -69.00   7.00   0.50    0.20    --  -49.73  76.00 101.00  152
 62  ω    -80.00 -55.00   0.50    0.75    --  -90.00  76.00 101.00   50
 63  ω    -43.00 -17.00   0.50    0.75    --  -90.00  15.00 -60.00   52
 64  ω    -55.00 -29.00   0.50    0.75    --  -90.00  45.00 -60.00   52
 65  ω    -65.00 -30.00   0.50    0.20    --  -49.73 -76.00 -25.00   70
 66  ω   -121.00 -68.00   0.50    0.20    --  -49.73 -76.00 -25.00  106
 67  ω   -116.00 -91.00   0.50    0.75    --  -90.00 -76.00 -25.00   50
 68  ω   -117.00 -91.00   0.50    0.20    --  -49.73-125.00 150.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku, XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1197398000
_diffrn_orient_matrix_UB_12      0.1570715000
_diffrn_orient_matrix_UB_13      0.0592880000
_diffrn_orient_matrix_UB_21      -0.0581251000
_diffrn_orient_matrix_UB_22      0.1250333000
_diffrn_orient_matrix_UB_23      -0.1105786000
_diffrn_orient_matrix_UB_31      -0.1908332000
_diffrn_orient_matrix_UB_32      -0.1366385000
_diffrn_orient_matrix_UB_33      -0.0330120000
_diffrn_oxdiff_digest_frames     
;
015c862c7604d8591b2ca4b778feb2647b000452cc7
;
_diffrn_oxdiff_digest_hkl        
;
01c32b9b0843348a1fc5d0394c6b5fa33f8d20
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.969
_reflns_limit_h_max              8
_reflns_limit_h_min              -8
_reflns_limit_k_max              8
_reflns_limit_k_min              -8
_reflns_limit_l_max              15
_reflns_limit_l_min              -15
_reflns_number_gt                2168
_reflns_number_total             2179
_reflns_odcompleteness_completeness 99.34
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.07
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'SIR2011 (Burla et al.,  2007)'
_refine_diff_density_max         0.2441
_refine_diff_density_min         -0.2481
_refine_diff_density_rms         0.0413
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.02(3)
_refine_ls_d_res_high            0.7824
_refine_ls_d_res_low             11.8766
_refine_ls_goodness_of_fit_ref   1.0728
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    20
_refine_ls_number_parameters     123
_refine_ls_number_reflns         2179
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0312
_refine_ls_R_factor_gt           0.0311
_refine_ls_restrained_S_all      1.0728
_refine_ls_shift/su_max          0.0013
_refine_ls_shift/su_mean         0.0005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0571P)²+0.1299P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0866
_refine_ls_wR_factor_ref         0.0868
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C4(H4a,H4b), C5(H5a,H5b)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12), C13(H13)
2.c Idealised Me refined as rotating group:
 C7(H7a,H7b,H7c)
;
_atom_sites_solution_primary     direct
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_refinement_flags_posn
S1 S 0.77739(5) 0.38853(7) 0.43541(3) 0.02522(12) Uani 1.000000 .
N2 N 0.6157(2) 0.5559(2) 0.39588(13) 0.0282(3) Uani 1.000000 .
C3 C 0.4475(3) 0.4645(3) 0.31313(14) 0.0262(3) Uani 1.000000 .
H3 H 0.323(3) 0.452(4) 0.3453(19) 0.028(5) Uiso 1.000000 .
C4 C 0.5088(3) 0.2401(3) 0.28153(15) 0.0303(4) Uani 1.000000 .
H4a H 0.3878(3) 0.1507(3) 0.25817(15) 0.0364(4) Uiso 1.000000 R
H4b H 0.5853(3) 0.2460(3) 0.21916(15) 0.0364(4) Uiso 1.000000 R
C5 C 0.6405(3) 0.1533(3) 0.38814(16) 0.0288(4) Uani 1.000000 .
H5a H 0.7308(3) 0.0392(3) 0.37144(16) 0.0345(5) Uiso 1.000000 R
H5b H 0.5590(3) 0.1025(3) 0.44295(16) 0.0345(5) Uiso 1.000000 R
O6 O 0.97124(18) 0.3979(3) 0.39883(12) 0.0384(3) Uani 1.000000 .
C7 C 0.8315(2) 0.3892(4) 0.58406(14) 0.0316(3) Uani 1.000000 .
H7a H 0.9382(18) 0.2863(19) 0.61075(14) 0.0474(5) Uiso 1.000000 GR
H7b H 0.877(2) 0.5300(8) 0.61103(14) 0.0474(5) Uiso 1.000000 GR
H7c H 0.7096(7) 0.352(3) 0.61290(14) 0.0474(5) Uiso 1.000000 GR
C8 C 0.3892(3) 0.6029(3) 0.21016(14) 0.0264(3) Uani 1.000000 .
C9 C 0.5345(3) 0.7154(3) 0.16612(15) 0.0284(3) Uani 1.000000 .
H9 H 0.6719(3) 0.7099(3) 0.20281(15) 0.0340(4) Uiso 1.000000 R
C10 C 0.4801(3) 0.8354(3) 0.06916(16) 0.0319(4) Uani 1.000000 .
H10 H 0.5803(3) 0.9106(3) 0.03949(16) 0.0382(5) Uiso 1.000000 R
C11 C 0.2795(3) 0.8455(3) 0.01557(16) 0.0349(4) Uani 1.000000 .
H11 H 0.2422(3) 0.9275(3) -0.05081(16) 0.0419(5) Uiso 1.000000 R
C12 C 0.1343(3) 0.7359(4) 0.05903(17) 0.0388(4) Uani 1.000000 .
H12 H -0.0031(3) 0.7431(4) 0.02251(17) 0.0466(5) Uiso 1.000000 R
C13 C 0.1883(3) 0.6148(3) 0.15611(17) 0.0345(4) Uani 1.000000 .
H13 H 0.0875(3) 0.5401(3) 0.18556(17) 0.0414(5) Uiso 1.000000 R


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 N2 1.5327(16) . ?
S1 C5 1.7907(19) . ?
S1 O6 1.4561(12) . ?
S1 C7 1.7658(16) . ?
N2 C3 1.483(2) . ?
C3 C4 1.550(2) . ?
C3 C8 1.514(2) . ?
C4 C5 1.525(3) . ?
C8 C9 1.394(2) . ?
C8 C13 1.392(3) . ?
C9 C10 1.388(3) . ?
C10 C11 1.387(3) . ?
C11 C12 1.382(3) . ?
C12 C13 1.393(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
C5 S1 N2 100.58(9) . . ?
O6 S1 N2 120.19(10) . . ?
O6 S1 C5 112.03(9) . . ?
C7 S1 N2 108.41(9) . . ?
C7 S1 C5 108.87(10) . . ?
C7 S1 O6 106.36(8) . . ?
C3 N2 S1 110.43(13) . . ?
C4 C3 N2 108.68(14) . . ?
C8 C3 N2 112.12(15) . . ?
C8 C3 C4 111.72(14) . . ?
C5 C4 C3 105.25(14) . . ?
C4 C5 S1 98.82(12) . . ?
C9 C8 C3 121.16(16) . . ?
C13 C8 C3 119.89(16) . . ?
C13 C8 C9 118.93(16) . . ?
C10 C9 C8 120.60(17) . . ?
C11 C10 C9 120.06(17) . . ?
C12 C11 C10 119.79(17) . . ?
C13 C12 C11 120.34(17) . . ?
C12 C13 C8 120.29(18) . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.417
_oxdiff_exptl_absorpt_empirical_full_min 0.597
