# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# 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_2c
_database_code_depnum_ccdc_archive 'CCDC 2444500'
loop_
_audit_author_name
_audit_author_address
'Victor Khrustalev'
;Peoples Friendship University of Russia (RUDN University, Moscow)
Russia
;
_audit_update_record             
;
2025-04-16 deposited with the CCDC.	2025-07-01 downloaded from the CCDC.
;
_audit_creation_date             2022-08-29
_audit_creation_method           
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H17 N3 O2 S, 2(C2 H6 O S)'
_chemical_formula_sum            'C22 H29 N3 O4 S3'
_chemical_formula_weight         495.66
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
_chemical_oxdiff_usercomment     C3395
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.20740(6)
_cell_length_b                   8.83930(8)
_cell_length_c                   17.27472(17)
_cell_angle_alpha                97.5406(8)
_cell_angle_beta                 97.5177(7)
_cell_angle_gamma                94.5922(7)
_cell_volume                     1225.681(19)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    45819
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      77.6300
_cell_measurement_theta_min      2.5660
_shelx_estimated_absorpt_T_max   0.712
_shelx_estimated_absorpt_T_min   0.462
_exptl_absorpt_coefficient_mu    3.042
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.487
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.58a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             524
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 -1 0.1003
0 1 1 0.0892
1 0 -1 0.1277
-1 0 1 0.1251
0 0 1 0.0622
0 0 -1 0.0604
0 -1 1 0.0937
0 1 -1 0.0799
1 0 1 0.1198

_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.12
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0000 -0.9992 -1.0002 -0.0526 -0.1787 0.0966
0.0000 0.9992 1.0002 0.0526 0.1787 -0.0966
0.9995 -0.0000 -0.9992 0.0886 0.0409 0.1731
-0.9995 0.0000 0.9992 -0.0886 -0.0409 -0.1731
-0.0001 -0.0002 0.9995 -0.0592 0.0663 -0.0188
0.0001 0.0002 -0.9995 0.0592 -0.0663 0.0188
-0.0001 -0.9996 0.9988 -0.1709 -0.0461 0.0591
0.0001 0.9996 -0.9988 0.1709 0.0461 -0.0591
0.9994 -0.0004 0.9998 -0.0298 0.1735 0.1355

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_unetI/netI     0.0131
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            61865
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.810
_diffrn_reflns_theta_min         2.607
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_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 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     38.00  65.00   0.50    0.10    --  107.75 -77.00 120.00   54
  2  ω     79.00 104.00   0.50    0.10    --  107.75 -77.00 120.00   50
  3  ω     71.00 105.00   0.50    0.10    --  107.75 -77.00  60.00   68
  4  ω     36.00  83.00   0.50    0.10    --  107.75 -77.00  90.00   94
  5  ω     38.00  64.00   0.50    0.10    --  107.75 -77.00  60.00   52
  6  ω     45.00  70.00   0.50    0.10    --  107.75 -62.00 149.75   50
  7  ω     37.00  79.00   0.50    0.10    --  107.75 -77.00 -90.00   84
  8  ω     74.00 102.00   0.50    0.10    --  107.75 -77.00-150.00   56
  9  ω     42.00  68.00   0.50    0.10    --  107.75 -77.00-150.00   52
 10  ω     37.00  67.00   0.50    0.10    --  107.75 -61.00-180.00   60
 11  ω     55.00  97.00   0.50    0.10    --  107.75 -77.00-180.00   84
 12  ω     42.00  68.00   0.50    0.10    --  107.75 -61.00-150.00   52
 13  ω     45.00  70.00   0.50    0.10    --  107.75 -61.00 -90.00   50
 14  ω     36.00  70.00   0.50    0.10    --  107.75 -61.00 -30.00   68
 15  ω     39.00  70.00   0.50    0.10    --  107.75 -61.00   0.00   62
 16  ω     37.00  68.00   0.50    0.10    --  107.75 -61.00-120.00   62
 17  ω     44.00  70.00   0.50    0.10    --  107.75 -61.00  60.00   52
 18  ω     36.00  61.00   0.50    0.10    --  107.75 -61.00  90.00   50
 19  ω     36.00  70.00   0.50    0.10    --  107.75 -61.00 120.00   68
 20  ω    102.00 140.00   0.50    0.10    --  107.75  15.00  60.00   76
 21  ω    122.00 176.00   0.50    0.10    --  107.75  77.00 120.00  108
 22  ω     89.00 114.00   0.50    0.10    --  107.75  77.00 120.00   50
 23  ω     36.00 130.00   0.50    0.05    --   58.00  77.00 107.51  188
 24  ω     44.00 138.00   0.50    0.05    --   66.00  77.00  30.35  188
 25  ω    153.00 178.00   0.50    0.10    --  107.75  77.00  60.00   50
 26  ω     86.00 139.00   0.50    0.10    --  107.75  77.00  60.00  106
 27  ω    123.00 178.00   0.50    0.10    --  107.75  77.00 -60.00  110
 28  ω    136.00 172.00   0.50    0.10    --  107.75  77.00 -90.00   72
 29  ω    141.00 177.00   0.50    0.10    --  107.75  77.00-120.00   72
 30  ω     87.00 147.00   0.50    0.10    --  107.75  77.00-150.00  120
 31  ω     90.00 121.00   0.50    0.10    --  107.75  77.00 -90.00   62
 32  ω     86.00 111.00   0.50    0.10    --  107.75  77.00 -60.00   50
 33  ω     88.00 136.00   0.50    0.10    --  107.75  77.00-120.00   96
 34  ω    135.00 170.00   0.50    0.10    --  107.75  77.00  30.00   70
 35  ω    142.00 177.00   0.50    0.10    --  107.75  77.00   0.00   70
 36  ω     88.00 118.00   0.50    0.10    --  107.75  77.00 -30.00   60
 37  ω     86.00 115.00   0.50    0.10    --  107.75  77.00  30.00   58
 38  ω     86.00 135.00   0.50    0.10    --  107.75  77.00  90.00   98
 39  ω     87.00 140.00   0.50    0.10    --  107.75  77.00 150.00  106
 40  ω     33.00 125.00   0.50    0.05    --   54.00  76.00 105.41  184
 41  ω     37.00 130.00   0.50    0.05    --   58.00  76.00  65.82  186
 42  ω     86.00 112.00   0.50    0.10    --  107.75  77.00   0.00   52
 43  ω     87.00 178.00   0.50    0.10    --  107.75  75.00 164.07  182
 44  ω     49.00 142.00   0.50    0.05    --   70.00  76.00-105.75  186
 45  ω     88.00 142.00   0.50    0.10    --  107.75  77.00-180.00  108
 46  ω     34.00 125.00   0.50    0.05    --   54.00  74.00-169.30  182
 47  ω     46.00 138.00   0.50    0.05    --   66.00  72.00-167.65  184
 48  ω     33.00 125.00   0.50    0.05    --   54.00  76.00-108.85  184
 49  ω     42.00 134.00   0.50    0.05    --   62.00  73.00   4.70  184
 50  ω     81.00 107.00   0.50    0.10    --   98.00  66.00 161.22   52
 51  ω    141.00 170.00   0.50    0.10    --  107.75  61.00  60.00   58
 52  ω     46.00 138.00   0.50    0.05    --   66.00  72.00 147.20  184
 53  ω     95.00 141.00   0.50    0.10    --  107.75  61.00 120.00   92
 54  ω     95.00 129.00   0.50    0.10    --  107.75  61.00  60.00   68
 55  ω     91.00 159.00   0.50    0.10    --  107.75  68.00 -28.72  136
 56  ω    103.00 157.00   0.50    0.10    --  107.75  61.00 -60.00  108
 57  ω     93.00 135.00   0.50    0.10    --  107.75  61.00 -90.00   84
 58  ω     94.00 121.00   0.50    0.10    --  107.75  61.00-120.00   54
 59  ω     93.00 127.00   0.50    0.10    --  107.75  61.00-150.00   68
 60  ω    123.00 177.00   0.50    0.10    --  107.75  61.00-180.00  108
 61  ω    139.00 169.00   0.50    0.10    --  107.75  61.00-150.00   60
 62  ω     93.00 130.00   0.50    0.10    --  107.75  61.00   0.00   74
 63  ω     93.00 164.00   0.50    0.10    --  107.75  61.00 -30.00  142
 64  ω     95.00 172.00   0.50    0.10    --  107.75  61.00  30.00  154
 65  ω     98.00 161.00   0.50    0.10    --  107.75  61.00  90.00  126
 66  ω    116.00 147.00   0.50    0.10    --  107.75  61.00 150.00   62
 67  ω    100.00 144.00   0.50    0.10    --  107.75  45.00 150.00   88
 68  ω    153.00 178.00   0.50    0.10    --  107.75  45.00 150.00   50
 69  ω    113.00 159.00   0.50    0.10    --  107.75  30.00  90.00   92
 70  ω    129.00 156.00   0.50    0.10    --  107.75  45.00  60.00   54
 71  ω    139.00 166.00   0.50    0.10    --  107.75  45.00   0.00   54
 72  ω     97.00 174.00   0.50    0.10    --  107.75  45.00-120.00  154
 73  ω    100.00 125.00   0.50    0.10    --  107.75  30.00-150.00   50
 74  ω    144.00 178.00   0.50    0.10    --  107.75  30.00 -90.00   68
 75  ω    119.00 176.00   0.50    0.10    --  107.75  30.00 -60.00  114
 76  ω    139.00 169.00   0.50    0.10    --  107.75 129.00 131.84   60
 77  ω    128.00 176.00   0.50    0.10    --  107.75 125.00 120.00   96
 78  ω    117.00 164.00   0.50    0.10    --  107.75 125.00  90.00   94
 79  ω    103.00 178.00   0.50    0.10    --  107.75 111.00 178.00  150
 80  ω     27.00 120.00   0.50    0.05    --   48.70  77.00 150.00  186
 81  ω     39.00 122.00   0.50    0.05    --   48.70  19.00  90.00  166
 82  ω     39.00 122.00   0.50    0.05    --   48.70  19.00 -30.00  166
 83  ω     27.00 120.00   0.50    0.05    --   48.70  77.00 -30.00  186
 84  ω     27.00 120.00   0.50    0.05    --   48.70  77.00 -60.00  186
 85  ω     27.00 120.00   0.50    0.05    --   48.70  77.00-120.00  186
 86  ω    -18.00  23.00   0.50    0.05    --   14.00  99.00-178.73   82
 87  ω      5.00  41.00   0.50    0.05    --   34.00  92.00 -76.86   72
 88  ω      2.00  43.00   0.50    0.05    --   30.00  90.00  66.18   82
 89  ω    -93.00 -64.00   0.50    0.10    --  -86.25 -77.00 120.00   58
 90  ω    -96.00 -64.00   0.50    0.10    --  -86.25 -77.00  30.00   64
 91  ω    -90.00 -64.00   0.50    0.10    --  -86.25 -77.00   0.00   52
 92  ω    -92.00 -66.00   0.50    0.10    --  -86.25 -76.00 -52.73   52
 93  ω   -147.00 -64.00   0.50    0.10    --  -86.25 -77.00 -90.00  166
 94  ω   -138.00 -45.00   0.50    0.05    --  -66.00 -76.00-149.76  186
 95  ω    -89.00 -64.00   0.50    0.10    --  -86.25 -77.00-120.00   50
 96  ω    -90.00 -65.00   0.50    0.10    --  -86.25 -75.00 -70.61   50
 97  ω    -85.00 -57.00   0.50    0.10    --  -78.00 -75.00  32.04   56
 98  ω    -82.00 -57.00   0.50    0.10    --  -78.00 -74.00  39.32   50
 99  ω    -82.00 -57.00   0.50    0.10    --  -78.00 -74.00  71.76   50
100  ω    -82.00 -57.00   0.50    0.10    --  -78.00 -74.00 126.19   50
101  ω   -101.00 -66.00   0.50    0.10    --  -86.25 -73.00 133.34   70
102  ω   -146.00-120.00   0.50    0.10    --  -86.25 -73.00 155.08   52
103  ω    -94.00 -66.00   0.50    0.10    --  -86.25 -73.00 155.08   56
104  ω   -145.00 -54.00   0.50    0.10    --  -74.00 -73.00  46.36  182
105  ω    -99.00 -66.00   0.50    0.10    --  -86.25 -72.00  89.46   66
106  ω    -99.00 -66.00   0.50    0.10    --  -86.25 -73.00  15.86   66
107  ω    -79.00 -54.00   0.50    0.10    --  -74.00 -73.00 -43.50   50
108  ω   -123.00 -66.00   0.50    0.10    --  -86.25 -72.00-117.90  114
109  ω   -127.00 -97.00   0.50    0.10    --  -86.25 -72.00-167.76   60
110  ω    -92.00 -66.00   0.50    0.10    --  -86.25 -72.00-167.76   52
111  ω   -107.00 -66.00   0.50    0.10    --  -86.25 -73.00-146.38   82
112  ω   -138.00 -47.00   0.50    0.05    --  -66.00 -69.00 -97.17  182
113  ω   -138.00 -49.00   0.50    0.05    --  -66.00 -65.00 -82.51  178
114  ω    -96.00 -68.00   0.50    0.10    --  -86.25 -69.00 -54.53   56
115  ω   -104.00 -69.00   0.50    0.10    --  -86.25 -65.00 -42.13   70
116  ω   -142.00 -53.00   0.50    0.10    --  -70.00 -64.00 -47.42  178
117  ω    -99.00 -67.00   0.50    0.10    --  -86.25 -70.00 176.70   64
118  ω   -138.00 -47.00   0.50    0.05    --  -66.00 -69.00 173.43  182
119  ω   -158.00 -81.00   0.50    0.10    --  -86.25-111.00  84.00  154
120  ω   -120.00 -27.00   0.50    0.05    --  -48.70 -77.00  30.00  186
121  ω   -121.00 -39.00   0.50    0.05    --  -48.70 -38.00  60.00  164
122  ω   -120.00 -27.00   0.50    0.05    --  -48.70 -77.00-180.00  186
123  ω     95.00 132.00   0.50    0.10    --  107.75 -83.00-109.67   74
124  ω     82.00 110.00   0.50    0.10    --  107.75-125.00-120.00   56
125  ω     79.00 111.00   0.50    0.10    --  107.75-125.00-180.00   64
126  ω     37.00  63.00   0.50    0.10    --  107.75-125.00-180.00   52
127  ω     43.00  77.00   0.50    0.10    --  107.75-125.00-120.00   68
128  ω     34.00  95.00   0.50    0.05    --   48.70-125.00   0.00  122
129  ω     36.00  61.00   0.50    0.10    --  107.75-125.00 120.00   50
130  ω     66.00  92.00   0.50    0.10    --  107.75-125.00 120.00   52
131  ω     65.00 111.00   0.50    0.10    --  107.75-125.00  90.00   92
132  ω     24.00  88.00   0.50    0.05    --   48.70-111.00  84.00  128
133  ω     37.00  62.00   0.50    0.10    --  107.75-125.00   0.00   50
134  ω     77.00 111.00   0.50    0.10    --  107.75-125.00   0.00   68
135  ω     36.00 108.00   0.50    0.10    --  107.75-111.00  84.00  144
136  ω     36.00  61.00   0.50    0.10    --  107.75-107.00 -15.07   50
137  ω     80.00 105.00   0.50    0.10    --  107.75 -95.00  30.00   50
138  ω     80.00 105.00   0.50    0.10    --  107.75 -95.00  90.00   50
139  ω     83.00 108.00   0.50    0.10    --  107.75-107.00 -15.07   50
140  ω     38.00  63.00   0.50    0.10    --  107.75 -95.00  90.00   50
141  ω     80.00 105.00   0.50    0.10    --  107.75 -95.00 -30.00   50
142  ω     40.00  66.00   0.50    0.10    --  107.75 -95.00 -30.00   52
143  ω     74.00 108.00   0.50    0.10    --  107.75-111.00 -66.65   68
144  ω     81.00 107.00   0.50    0.10    --  107.75-114.00 -92.60   52
145  ω     38.00  63.00   0.50    0.10    --  107.75 -83.00-109.67   50
146  ω     37.00  81.00   0.50    0.10    --  107.75 -95.00-180.00   88
147  ω    -43.00  24.00   0.50    0.05    --  -48.70  38.00-180.00  134
148  ω    -82.00  -2.00   0.50    0.05    --  -48.70 111.00 178.00  160
149  ω    -72.00 -47.00   0.50    0.10    --  -86.25 111.00 178.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  '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      0.0294920000
_diffrn_orient_matrix_UB_12      0.1118534000
_diffrn_orient_matrix_UB_13      -0.0591887000
_diffrn_orient_matrix_UB_21      0.1072562000
_diffrn_orient_matrix_UB_22      0.1123865000
_diffrn_orient_matrix_UB_23      0.0663722000
_diffrn_orient_matrix_UB_31      0.1543599000
_diffrn_orient_matrix_UB_32      -0.0779182000
_diffrn_orient_matrix_UB_33      -0.0187854000
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5112
_reflns_number_total             5196
_reflns_odcompleteness_completeness 98.26
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     78.52
_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 1.171.42.58a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     314
_refine_ls_number_reflns         5196
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0306
_refine_ls_R_factor_gt           0.0302
_refine_ls_restrained_S_all      1.031
_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)+(0.0400P)²+0.6782P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0772
_refine_ls_wR_factor_ref         0.0775
_refine_special_details          ?
_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. Restrained distances
 S1-O1 \\sim O20-S20
 with sigma of 0.02
 S20-C21 \\sim S20-C21A
 with sigma of 0.02
 S20-C22 \\sim S20-C22A
 with sigma of 0.02
 C21-S1 \\sim C21A-S1
 with sigma of 0.02
 C22-S1 \\sim C22A-S1
 with sigma of 0.02
3. Rigid bond restraints
 C5, S5
 with sigma for 1-2 distances of 0.0005 and sigma for 1-3 distances of 0.0005
4. Uiso/Uaniso restraints and constraints
Uanis(S1) = Uanis(S20)
Uanis(O20) = Uanis(O1)
Uanis(C21) = Uanis(C21A)
Uanis(C22) = Uanis(C22A)
5. Others
 Sof(C21)=Sof(H21D)=Sof(H21E)=Sof(H21F)=Sof(C22)=Sof(H22D)=Sof(H22E)=Sof(H22F)=
 Sof(S1)=Sof(O1)=1-FVAR(1)
 Sof(S20)=Sof(O20)=Sof(C21A)=Sof(H21A)=Sof(H21B)=Sof(H21C)=Sof(C22A)=Sof(H22A)=
 Sof(H22B)=Sof(H22C)=FVAR(1)
6.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C14(H14), C18(H18), C12(H12), C15(H15), C9(H9), C16(H16), C17(H17),
 C10(H10), C11(H11)
6.b Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C1(H1A,H1B,H1C), C21(H21D,H21E,H21F), C22(H22D,H22E,H22F),
 C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C21A(H21A,H21B,H21C), C22A(H22A,H22B,
 H22C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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
S5 S 0.79697(4) 0.52729(3) 0.60638(2) 0.01811(8) Uani 1 1 d . U . . .
S23 S 0.32439(4) 0.70074(4) 0.69120(2) 0.02244(9) Uani 1 1 d . . . . .
S20 S 0.72588(5) 0.89892(4) 0.44037(2) 0.02192(11) Uani 0.8581(9) 1 d D . P A 1
O6 O 0.94392(10) 0.41922(10) 0.72854(5) 0.01486(17) Uani 1 1 d . . . . .
O2 O 1.01438(11) 0.66549(10) 0.95771(5) 0.01761(18) Uani 1 1 d . . . . .
O23 O 0.37715(12) 0.55131(12) 0.71548(6) 0.0283(2) Uani 1 1 d . . . . .
N4 N 0.68449(13) 0.45838(12) 0.73814(6) 0.0147(2) Uani 1 1 d . . . . .
N3 N 0.78192(12) 0.54632(11) 0.87588(6) 0.0147(2) Uani 1 1 d . . . . .
N1 N 1.02134(12) 0.44924(11) 0.86723(6) 0.0137(2) Uani 1 1 d . . . . .
O20 O 0.75513(15) 1.00995(14) 0.51509(8) 0.0351(3) Uani 0.8581(9) 1 d D . P A 1
C13 C 0.61652(14) 0.29579(13) 0.83786(7) 0.0133(2) Uani 1 1 d . . . . .
C2 C 0.94602(14) 0.56486(13) 0.90563(7) 0.0134(2) Uani 1 1 d . . . . .
C6A C 0.91439(14) 0.36227(13) 0.80278(6) 0.0127(2) Uani 1 1 d . . . . .
C7 C 0.93035(14) 0.19189(13) 0.79274(7) 0.0140(2) Uani 1 1 d . . . . .
C5 C 0.80502(15) 0.46811(13) 0.69381(7) 0.0140(2) Uani 1 1 d . U . . .
C8 C 0.96512(15) 0.12092(14) 0.85985(7) 0.0165(2) Uani 1 1 d . . . . .
H8 H 0.981947 0.180088 0.910778 0.020 Uiso 1 1 calc R U . . .
C14 C 0.48823(15) 0.21550(14) 0.78352(7) 0.0161(2) Uani 1 1 d . . . . .
H14 H 0.473833 0.236029 0.730566 0.019 Uiso 1 1 calc R U . . .
C18 C 0.63729(15) 0.26437(14) 0.91538(7) 0.0171(2) Uani 1 1 d . . . . .
H18 H 0.724092 0.319090 0.952849 0.020 Uiso 1 1 calc R U . . .
C3A C 0.73842(14) 0.41451(13) 0.81478(6) 0.0126(2) Uani 1 1 d . . . . .
C12 C 0.90478(15) 0.10461(14) 0.71821(7) 0.0175(2) Uani 1 1 d . . . . .
H12 H 0.878514 0.152280 0.672578 0.021 Uiso 1 1 calc R U . . .
C3 C 0.66247(16) 0.64175(15) 0.90615(8) 0.0200(3) Uani 1 1 d . . . . .
H3A H 0.593227 0.583195 0.936174 0.030 Uiso 1 1 calc R U . . .
H3B H 0.592902 0.674525 0.862072 0.030 Uiso 1 1 calc R U . . .
H3C H 0.720458 0.732124 0.940696 0.030 Uiso 1 1 calc R U . . .
C1 C 1.20056(15) 0.45137(15) 0.87495(7) 0.0183(2) Uani 1 1 d . . . . .
H1A H 1.237037 0.463638 0.824134 0.027 Uiso 1 1 calc R U . . .
H1B H 1.233618 0.354766 0.891091 0.027 Uiso 1 1 calc R U . . .
H1C H 1.251489 0.537138 0.914797 0.027 Uiso 1 1 calc R U . . .
C15 C 0.38100(15) 0.10522(14) 0.80658(8) 0.0194(2) Uani 1 1 d . . . . .
H15 H 0.292689 0.051810 0.769523 0.023 Uiso 1 1 calc R U . . .
C9 C 0.97505(16) -0.03681(15) 0.85190(8) 0.0204(3) Uani 1 1 d . . . . .
H9 H 0.996856 -0.085565 0.897493 0.025 Uiso 1 1 calc R U . . .
C16 C 0.40287(16) 0.07323(15) 0.88345(8) 0.0212(3) Uani 1 1 d . . . . .
H16 H 0.330565 -0.002952 0.898967 0.025 Uiso 1 1 calc R U . . .
C17 C 0.53096(16) 0.15299(15) 0.93782(8) 0.0207(3) Uani 1 1 d . . . . .
H17 H 0.545888 0.131246 0.990558 0.025 Uiso 1 1 calc R U . . .
C10 C 0.95312(16) -0.12281(14) 0.77741(9) 0.0230(3) Uani 1 1 d . . . . .
H10 H 0.962314 -0.230017 0.772082 0.028 Uiso 1 1 calc R U . . .
C21 C 0.879(9) 0.758(7) 0.440(4) 0.0243(9) Uani 0.1419(9) 1 d . . P A 2
H21D H 0.897931 0.675542 0.471854 0.036 Uiso 0.1419(9) 1 calc R U P A 2
H21E H 0.983601 0.818220 0.438869 0.036 Uiso 0.1419(9) 1 calc R U P A 2
H21F H 0.829753 0.714104 0.386277 0.036 Uiso 0.1419(9) 1 calc R U P A 2
C11 C 0.91776(16) -0.05258(15) 0.71063(8) 0.0221(3) Uani 1 1 d . . . . .
H11 H 0.902419 -0.111854 0.659754 0.027 Uiso 1 1 calc R U . . .
C22 C 0.561(3) 0.755(3) 0.4686(12) 0.0247(5) Uani 0.1419(9) 1 d . . P A 2
H22D H 0.533412 0.715626 0.412203 0.037 Uiso 0.1419(9) 1 calc R U P A 2
H22E H 0.468997 0.807343 0.486592 0.037 Uiso 0.1419(9) 1 calc R U P A 2
H22F H 0.580481 0.669329 0.498253 0.037 Uiso 0.1419(9) 1 calc R U P A 2
C24 C 0.51113(17) 0.81465(16) 0.68540(9) 0.0260(3) Uani 1 1 d . . . . .
H24A H 0.570465 0.848485 0.738666 0.039 Uiso 1 1 calc R U . . .
H24B H 0.484753 0.904417 0.660148 0.039 Uiso 1 1 calc R U . . .
H24C H 0.580589 0.753537 0.654215 0.039 Uiso 1 1 calc R U . . .
C25 C 0.25220(19) 0.65906(17) 0.58816(9) 0.0291(3) Uani 1 1 d . . . . .
H25A H 0.334700 0.606971 0.561382 0.044 Uiso 1 1 calc R U . . .
H25B H 0.233980 0.754809 0.566935 0.044 Uiso 1 1 calc R U . . .
H25C H 0.148198 0.592472 0.579455 0.044 Uiso 1 1 calc R U . . .
H4 H 0.592(2) 0.490(2) 0.7261(10) 0.025(4) Uiso 1 1 d . . . . .
S1 S 0.7373(3) 0.8828(3) 0.48383(18) 0.02192(11) Uani 0.1419(9) 1 d D . P A 2
O1 O 0.7021(9) 0.9954(9) 0.4248(5) 0.0351(3) Uani 0.1419(9) 1 d D . P A 2
C21A C 0.8857(13) 0.7746(10) 0.4449(7) 0.0243(9) Uani 0.8581(9) 1 d . . P A 1
H21A H 0.992797 0.834696 0.448644 0.036 Uiso 0.8581(9) 1 calc R U P A 1
H21B H 0.868707 0.698614 0.397165 0.036 Uiso 0.8581(9) 1 calc R U P A 1
H21C H 0.883589 0.722121 0.491360 0.036 Uiso 0.8581(9) 1 calc R U P A 1
C22A C 0.5592(5) 0.7616(4) 0.44961(12) 0.0247(5) Uani 0.8581(9) 1 d . . P A 1
H22A H 0.583077 0.720347 0.499388 0.037 Uiso 0.8581(9) 1 calc R U P A 1
H22B H 0.546702 0.677851 0.405409 0.037 Uiso 0.8581(9) 1 calc R U P A 1
H22C H 0.456741 0.811482 0.449080 0.037 Uiso 0.8581(9) 1 calc R U P A 1


_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
S5 C5 1.6571(12) . ?
S23 O23 1.5157(10) . ?
S23 C24 1.7868(15) . ?
S23 C25 1.7811(15) . ?
S20 O20 1.4953(13) . ?
S20 C21A 1.777(11) . ?
S20 C22A 1.792(4) . ?
O6 C6A 1.4792(13) . ?
O6 C5 1.3469(14) . ?
O2 C2 1.2220(15) . ?
N4 C5 1.3320(16) . ?
N4 C3A 1.4518(14) . ?
N4 H4 0.838(18) . ?
N3 C2 1.3662(15) . ?
N3 C3A 1.4530(14) . ?
N3 C3 1.4480(15) . ?
N1 C2 1.3773(15) . ?
N1 C6A 1.4187(14) . ?
N1 C1 1.4578(15) . ?
C13 C14 1.3929(16) . ?
C13 C18 1.3947(16) . ?
C13 C3A 1.5190(15) . ?
C6A C7 1.5114(16) . ?
C6A C3A 1.5818(16) . ?
C7 C8 1.3972(17) . ?
C7 C12 1.3927(16) . ?
C8 H8 0.9500 . ?
C8 C9 1.3929(17) . ?
C14 H14 0.9500 . ?
C14 C15 1.3927(17) . ?
C18 H18 0.9500 . ?
C18 C17 1.3900(17) . ?
C12 H12 0.9500 . ?
C12 C11 1.3924(18) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C15 H15 0.9500 . ?
C15 C16 1.3856(19) . ?
C9 H9 0.9500 . ?
C9 C10 1.3882(19) . ?
C16 H16 0.9500 . ?
C16 C17 1.3905(19) . ?
C17 H17 0.9500 . ?
C10 H10 0.9500 . ?
C10 C11 1.389(2) . ?
C21 H21D 0.9800 . ?
C21 H21E 0.9800 . ?
C21 H21F 0.9800 . ?
C21 S1 1.83(6) . ?
C11 H11 0.9500 . ?
C22 H22D 0.9800 . ?
C22 H22E 0.9800 . ?
C22 H22F 0.9800 . ?
C22 S1 1.73(3) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
S1 O1 1.533(9) . ?
C21A H21A 0.9800 . ?
C21A H21B 0.9800 . ?
C21A H21C 0.9800 . ?
C22A H22A 0.9800 . ?
C22A H22B 0.9800 . ?
C22A H22C 0.9800 . ?

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
O23 S23 C24 105.69(6) . . ?
O23 S23 C25 105.50(7) . . ?
C25 S23 C24 97.73(7) . . ?
O20 S20 C21A 107.3(3) . . ?
O20 S20 C22A 106.74(11) . . ?
C21A S20 C22A 97.6(4) . . ?
C5 O6 C6A 110.21(9) . . ?
C5 N4 C3A 113.22(10) . . ?
C5 N4 H4 122.6(12) . . ?
C3A N4 H4 123.3(12) . . ?
C2 N3 C3A 112.91(9) . . ?
C2 N3 C3 123.29(10) . . ?
C3 N3 C3A 123.67(10) . . ?
C2 N1 C6A 112.43(10) . . ?
C2 N1 C1 121.78(10) . . ?
C6A N1 C1 122.67(10) . . ?
C14 C13 C18 119.51(11) . . ?
C14 C13 C3A 121.92(10) . . ?
C18 C13 C3A 118.55(10) . . ?
O2 C2 N3 126.15(11) . . ?
O2 C2 N1 125.74(11) . . ?
N3 C2 N1 108.11(10) . . ?
O6 C6A C7 108.10(9) . . ?
O6 C6A C3A 102.82(8) . . ?
N1 C6A O6 109.80(9) . . ?
N1 C6A C7 114.81(10) . . ?
N1 C6A C3A 103.59(9) . . ?
C7 C6A C3A 116.97(9) . . ?
C8 C7 C6A 119.00(10) . . ?
C12 C7 C6A 121.05(11) . . ?
C12 C7 C8 119.91(11) . . ?
O6 C5 S5 121.13(9) . . ?
N4 C5 S5 127.83(10) . . ?
N4 C5 O6 111.03(10) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 C7 119.84(12) . . ?
C9 C8 H8 120.1 . . ?
C13 C14 H14 119.9 . . ?
C15 C14 C13 120.22(11) . . ?
C15 C14 H14 119.9 . . ?
C13 C18 H18 120.0 . . ?
C17 C18 C13 120.00(11) . . ?
C17 C18 H18 120.0 . . ?
N4 C3A N3 112.34(9) . . ?
N4 C3A C13 112.70(9) . . ?
N4 C3A C6A 100.96(9) . . ?
N3 C3A C13 112.14(9) . . ?
N3 C3A C6A 101.46(9) . . ?
C13 C3A C6A 116.32(9) . . ?
C7 C12 H12 120.0 . . ?
C11 C12 C7 119.93(12) . . ?
C11 C12 H12 120.0 . . ?
N3 C3 H3A 109.5 . . ?
N3 C3 H3B 109.5 . . ?
N3 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C14 C15 H15 119.9 . . ?
C16 C15 C14 120.14(12) . . ?
C16 C15 H15 119.9 . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 120.04(12) . . ?
C10 C9 H9 120.0 . . ?
C15 C16 H16 120.1 . . ?
C15 C16 C17 119.80(12) . . ?
C17 C16 H16 120.1 . . ?
C18 C17 C16 120.33(12) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C9 C10 H10 119.9 . . ?
C9 C10 C11 120.20(12) . . ?
C11 C10 H10 119.9 . . ?
H21D C21 H21E 109.5 . . ?
H21D C21 H21F 109.5 . . ?
H21E C21 H21F 109.5 . . ?
S1 C21 H21D 109.5 . . ?
S1 C21 H21E 109.5 . . ?
S1 C21 H21F 109.5 . . ?
C12 C11 H11 120.0 . . ?
C10 C11 C12 120.06(12) . . ?
C10 C11 H11 120.0 . . ?
H22D C22 H22E 109.5 . . ?
H22D C22 H22F 109.5 . . ?
H22E C22 H22F 109.5 . . ?
S1 C22 H22D 109.5 . . ?
S1 C22 H22E 109.5 . . ?
S1 C22 H22F 109.5 . . ?
S23 C24 H24A 109.5 . . ?
S23 C24 H24B 109.5 . . ?
S23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
S23 C25 H25A 109.5 . . ?
S23 C25 H25B 109.5 . . ?
S23 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C22 S1 C21 99(2) . . ?
O1 S1 C21 105(3) . . ?
O1 S1 C22 104.6(8) . . ?
S20 C21A H21A 109.5 . . ?
S20 C21A H21B 109.5 . . ?
S20 C21A H21C 109.5 . . ?
H21A C21A H21B 109.5 . . ?
H21A C21A H21C 109.5 . . ?
H21B C21A H21C 109.5 . . ?
S20 C22A H22A 109.5 . . ?
S20 C22A H22B 109.5 . . ?
S20 C22A H22C 109.5 . . ?
H22A C22A H22B 109.5 . . ?
H22A C22A H22C 109.5 . . ?
H22B C22A H22C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N4 H4 O23 0.838(18) 1.882(19) 2.7108(14) 170.3(17) . yes

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
O6 C6A C7 C8 157.95(10) . . . . ?
O6 C6A C7 C12 -24.51(14) . . . . ?
O6 C6A C3A N4 12.51(10) . . . . ?
O6 C6A C3A N3 -103.23(9) . . . . ?
O6 C6A C3A C13 134.80(9) . . . . ?
N1 C6A C7 C8 35.02(15) . . . . ?
N1 C6A C7 C12 -147.44(11) . . . . ?
N1 C6A C3A N4 126.86(9) . . . . ?
N1 C6A C3A N3 11.12(11) . . . . ?
N1 C6A C3A C13 -110.84(10) . . . . ?
C13 C14 C15 C16 -0.93(19) . . . . ?
C13 C18 C17 C16 -0.48(19) . . . . ?
C2 N3 C3A N4 -114.10(11) . . . . ?
C2 N3 C3A C13 117.76(11) . . . . ?
C2 N3 C3A C6A -7.06(12) . . . . ?
C2 N1 C6A O6 96.94(11) . . . . ?
C2 N1 C6A C7 -141.04(10) . . . . ?
C2 N1 C6A C3A -12.30(12) . . . . ?
C6A O6 C5 S5 -175.76(8) . . . . ?
C6A O6 C5 N4 3.18(13) . . . . ?
C6A N1 C2 O2 -172.23(11) . . . . ?
C6A N1 C2 N3 8.37(13) . . . . ?
C6A C7 C8 C9 177.95(11) . . . . ?
C6A C7 C12 C11 -179.02(11) . . . . ?
C7 C6A C3A N4 -105.74(11) . . . . ?
C7 C6A C3A N3 138.52(10) . . . . ?
C7 C6A C3A C13 16.56(14) . . . . ?
C7 C8 C9 C10 1.05(19) . . . . ?
C7 C12 C11 C10 1.20(19) . . . . ?
C5 O6 C6A N1 -119.88(10) . . . . ?
C5 O6 C6A C7 114.19(10) . . . . ?
C5 O6 C6A C3A -10.13(11) . . . . ?
C5 N4 C3A N3 95.42(12) . . . . ?
C5 N4 C3A C13 -136.74(10) . . . . ?
C5 N4 C3A C6A -11.95(12) . . . . ?
C8 C7 C12 C11 -1.51(18) . . . . ?
C8 C9 C10 C11 -1.36(19) . . . . ?
C14 C13 C18 C17 0.38(18) . . . . ?
C14 C13 C3A N4 13.29(15) . . . . ?
C14 C13 C3A N3 141.24(11) . . . . ?
C14 C13 C3A C6A -102.61(13) . . . . ?
C14 C15 C16 C17 0.83(19) . . . . ?
C18 C13 C14 C15 0.33(18) . . . . ?
C18 C13 C3A N4 -168.36(10) . . . . ?
C18 C13 C3A N3 -40.41(14) . . . . ?
C18 C13 C3A C6A 75.74(13) . . . . ?
C3A N4 C5 S5 -174.85(9) . . . . ?
C3A N4 C5 O6 6.30(14) . . . . ?
C3A N3 C2 O2 -179.41(11) . . . . ?
C3A N3 C2 N1 -0.01(13) . . . . ?
C3A C13 C14 C15 178.67(11) . . . . ?
C3A C13 C18 C17 -178.02(11) . . . . ?
C3A C6A C7 C8 -86.69(13) . . . . ?
C3A C6A C7 C12 90.84(13) . . . . ?
C12 C7 C8 C9 0.38(18) . . . . ?
C3 N3 C2 O2 -3.54(19) . . . . ?
C3 N3 C2 N1 175.86(10) . . . . ?
C3 N3 C3A N4 70.05(14) . . . . ?
C3 N3 C3A C13 -58.09(14) . . . . ?
C3 N3 C3A C6A 177.09(10) . . . . ?
C1 N1 C2 O2 -11.75(18) . . . . ?
C1 N1 C2 N3 168.84(10) . . . . ?
C1 N1 C6A O6 -63.33(13) . . . . ?
C1 N1 C6A C7 58.68(14) . . . . ?
C1 N1 C6A C3A -172.58(10) . . . . ?
C15 C16 C17 C18 -0.1(2) . . . . ?
C9 C10 C11 C12 0.2(2) . . . . ?

_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 1.183
_oxdiff_exptl_absorpt_empirical_full_min 0.833
####################################################################### 
# 
# 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_HMPzOTf
_database_code_depnum_ccdc_archive 'CCDC 2444503'
loop_
_audit_author_name
_audit_author_address
'Victor Khrustalev'
;Peoples Friendship University of Russia (RUDN University, Moscow)
Russia
;
_audit_update_record             
;
2025-04-16 deposited with the CCDC.	2025-07-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C F3 O3 S, C4 H7 N2'
_chemical_formula_sum            'C5 H7 F3 N2 O3 S'
_chemical_formula_weight         232.19

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   6.7288(4)
_cell_length_b                   15.3912(9)
_cell_length_c                   8.7864(5)
_cell_angle_alpha                90
_cell_angle_beta                 96.7010(10)
_cell_angle_gamma                90
_cell_volume                     903.74(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9916
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      32.63

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.707
_exptl_crystal_F_000             472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.392
_shelx_estimated_absorpt_T_min   0.912
_shelx_estimated_absorpt_T_max   0.933
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.900
_exptl_absorpt_correction_T_max  0.921
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-III CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15739
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.647
_diffrn_reflns_theta_max         32.649
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.973
_reflns_number_total             3260
_reflns_number_gt                3043
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'APEX3 (Bruker, 2018)'
_computing_cell_refinement       'SAINT (Bruker, 2013)'
_computing_data_reduction        'SAINT (Bruker, 2013)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2015)'
_computing_publication_material  'SHELXTL (Sheldrick, 2015)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0445P)²+0.7084P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3260
_refine_ls_number_parameters     131
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0400
_refine_ls_wR_factor_ref         0.0988
_refine_ls_wR_factor_gt          0.0970
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.31086(4) 0.35902(2) 0.23052(3) 0.01474(8) Uani 1 1 d . . . . .
F1 F 0.18257(16) 0.48822(6) 0.38666(11) 0.0329(2) Uani 1 1 d . . . . .
F2 F -0.00840(19) 0.45515(9) 0.18386(16) 0.0570(4) Uani 1 1 d . . . . .
F3 F 0.0040(2) 0.37388(7) 0.38537(19) 0.0603(4) Uani 1 1 d . . . . .
O1 O 0.20805(15) 0.29421(7) 0.13433(13) 0.0282(2) Uani 1 1 d . . . . .
O2 O 0.4167(2) 0.42193(8) 0.15256(19) 0.0518(4) Uani 1 1 d . . . . .
O3 O 0.4167(3) 0.32382(11) 0.36745(14) 0.0571(5) Uani 1 1 d . . . . .
C1 C 0.1110(2) 0.42206(8) 0.30021(17) 0.0241(2) Uani 1 1 d . . . . .
N1 N 0.54420(14) 0.37045(6) 0.76749(11) 0.01520(17) Uani 1 1 d . . . . .
N2 N 0.61842(15) 0.33160(7) 0.64984(11) 0.01641(18) Uani 1 1 d . . . . .
H2 H 0.549(3) 0.3296(12) 0.567(2) 0.020 Uiso 1 1 d . U . . .
C2 C 0.34348(18) 0.40707(9) 0.75163(17) 0.0241(2) Uani 1 1 d . . . . .
H2A H 0.341189 0.460610 0.691069 0.036 Uiso 1 1 calc R U . . .
H2B H 0.304997 0.420153 0.853346 0.036 Uiso 1 1 calc R U . . .
H2C H 0.249084 0.365120 0.699782 0.036 Uiso 1 1 calc R U . . .
C3 C 0.80520(18) 0.30518(8) 0.69533(14) 0.0181(2) Uani 1 1 d . . . . .
H3 H 0.890930 0.275878 0.633671 0.022 Uiso 1 1 calc R U . . .
C4 C 0.85212(17) 0.32783(8) 0.84752(13) 0.0178(2) Uani 1 1 d . . . . .
H4 H 0.974264 0.317233 0.910540 0.021 Uiso 1 1 calc R U . . .
C5 C 0.68324(18) 0.36932(8) 0.88897(13) 0.0173(2) Uani 1 1 d . . . . .
H5 H 0.669070 0.392881 0.987055 0.021 Uiso 1 1 calc R U . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.4240(12) . ?
S1 O3 1.4312(12) . ?
S1 O1 1.4323(10) . ?
S1 C1 1.8215(13) . ?
F1 C1 1.3268(16) . ?
F2 C1 1.3259(18) . ?
F3 C1 1.3243(17) . ?
N1 C5 1.3348(15) . ?
N1 N2 1.3402(13) . ?
N1 C2 1.4551(15) . ?
N2 C3 1.3370(15) . ?
N2 H2 0.820(19) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 C4 1.3824(16) . ?
C3 H3 0.9500 . ?
C4 C5 1.3886(16) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?

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
O2 S1 O3 115.72(12) . . ?
O2 S1 O1 115.09(8) . . ?
O3 S1 O1 113.02(9) . . ?
O2 S1 C1 103.29(7) . . ?
O3 S1 C1 103.51(8) . . ?
O1 S1 C1 104.16(6) . . ?
F2 C1 F3 109.29(15) . . ?
F2 C1 F1 107.06(12) . . ?
F3 C1 F1 106.94(12) . . ?
F2 C1 S1 110.49(11) . . ?
F3 C1 S1 111.29(10) . . ?
F1 C1 S1 111.60(9) . . ?
C5 N1 N2 108.75(9) . . ?
C5 N1 C2 129.62(10) . . ?
N2 N1 C2 121.61(10) . . ?
C3 N2 N1 109.09(10) . . ?
C3 N2 H2 132.3(13) . . ?
N1 N2 H2 118.6(13) . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N2 C3 C4 108.25(10) . . ?
N2 C3 H3 125.9 . . ?
C4 C3 H3 125.9 . . ?
C3 C4 C5 105.56(10) . . ?
C3 C4 H4 127.2 . . ?
C5 C4 H4 127.2 . . ?
N1 C5 C4 108.36(10) . . ?
N1 C5 H5 125.8 . . ?
C4 C5 H5 125.8 . . ?

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
O2 S1 C1 F2 62.52(14) . . . . ?
O3 S1 C1 F2 -176.46(13) . . . . ?
O1 S1 C1 F2 -58.07(12) . . . . ?
O2 S1 C1 F3 -175.86(13) . . . . ?
O3 S1 C1 F3 -54.84(15) . . . . ?
O1 S1 C1 F3 63.55(13) . . . . ?
O2 S1 C1 F1 -56.48(13) . . . . ?
O3 S1 C1 F1 64.54(13) . . . . ?
O1 S1 C1 F1 -177.07(10) . . . . ?
C5 N1 N2 C3 0.14(13) . . . . ?
C2 N1 N2 C3 179.17(11) . . . . ?
N1 N2 C3 C4 0.07(14) . . . . ?
N2 C3 C4 C5 -0.25(14) . . . . ?
N2 N1 C5 C4 -0.29(13) . . . . ?
C2 N1 C5 C4 -179.22(12) . . . . ?
C3 C4 C5 N1 0.33(14) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N2 H2 O3 0.820(19) 1.872(19) 2.6882(15) 173.7(19) . yes
C3 H3 O1 0.95 2.39 3.2115(16) 144.5 4_666 yes
C4 H4 O1 0.95 2.40 3.3085(15) 160.7 1_656 yes
C5 H5 O2 0.95 2.40 3.1947(16) 140.6 1_556 yes

_refine_diff_density_max         0.919
_refine_diff_density_min         -0.596
_refine_diff_density_rms         0.064

####################################################################### 
# 
# 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_3a
_database_code_depnum_ccdc_archive 'CCDC 2444501'
loop_
_audit_author_name
_audit_author_address
'Victor Khrustalev'
;Peoples Friendship University of Russia (RUDN University, Moscow)
Russia
;
_audit_update_record             
;
2025-04-16 deposited with the CCDC.	2025-07-01 downloaded from the CCDC.
;
_audit_creation_date             2024-06-26
_audit_creation_method           
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H21 N3 O S2'
_chemical_formula_sum            'C20 H21 N3 O S2'
_chemical_formula_weight         383.52
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H21N3OS2
_chemical_oxdiff_usercomment     c3927
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.1644(3)
_cell_length_b                   9.0953(4)
_cell_length_c                   13.4123(7)
_cell_angle_alpha                72.506(4)
_cell_angle_beta                 77.901(4)
_cell_angle_gamma                83.548(3)
_cell_volume                     927.50(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5431
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      79.4750
_cell_measurement_theta_min      5.0930
_shelx_estimated_absorpt_T_max   0.833
_shelx_estimated_absorpt_T_min   0.450
_exptl_absorpt_coefficient_mu    2.712
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.298
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.124a (Rigaku Oxford Diffraction, 2024)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             404
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 1 0.0349
0 -1 -1 0.0322
0 -1 1 0.1092
0 1 -1 0.1294
-1 1 0 0.0805
1 -1 0 0.0781
1 0 1 0.0917
-1 0 -1 0.0820
1 0 0 0.1150
-1 0 0 0.1466

_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.07
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0001 0.9998 0.9969 0.1130 -0.0664 -0.1303
0.0001 -0.9998 -0.9969 -0.1130 0.0664 0.1303
-0.0010 -0.9969 1.0029 -0.0455 -0.1654 0.1719
0.0010 0.9969 -1.0029 0.0455 0.1654 -0.1719
-0.9991 0.9991 -0.0038 0.2498 0.0767 -0.0648
0.9991 -0.9991 0.0038 -0.2498 -0.0767 0.0648
0.9991 0.0007 1.0007 -0.1369 -0.1431 -0.0655
-0.9991 -0.0007 -1.0007 0.1369 0.1431 0.0655
0.9996 -0.0008 0.0008 -0.1706 -0.0272 -0.0863
-0.9996 0.0008 -0.0008 0.1706 0.0272 0.0863

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            24258
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.763
_diffrn_reflns_theta_min         3.516
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     27.00  87.00   0.50    0.06    --   44.12-114.00  60.00  120
  2  ω    -34.00  27.00   0.50    0.06    --   44.12 -19.00  60.00  122
  3  ω    -34.00  27.00   0.50    0.06    --   44.12 -19.00 -60.00  122
  4  ω     -1.00  81.00   0.50    0.06    --   44.12 -99.00-150.00  164
  5  ω     34.00  94.00   0.50    0.06    --   44.12-125.00-180.00  120
  6  ω     -1.00  81.00   0.50    0.06    --   44.12 -99.00-150.00  164
  7  ω    -34.00  27.00   0.50    0.06    --   44.12 -19.00-180.00  122
  8  ω    105.00 130.00   0.50    0.26    --  117.50 -82.00   3.16   50
  9  ω     47.00 111.00   0.50    0.26    --  117.50-125.00  60.00  128
 10  ω     47.00 111.00   0.50    0.26    --  117.50-125.00 150.00  128
 11  ω     48.00  73.00   0.50    0.26    --  117.50-125.00   0.00   50
 12  ω     47.00 111.00   0.50    0.26    --  117.50-125.00 -30.00  128
 13  ω     86.00 111.00   0.50    0.26    --  117.50-125.00   0.00   50
 14  ω     47.00  86.00   0.50    0.26    --  117.50-125.00  90.00   78
 15  ω     47.00 109.00   0.50    0.26    --  117.50-114.00  60.00  124
 16  ω     62.00 111.00   0.50    0.26    --  117.50-125.00-120.00   98
 17  ω     47.00 111.00   0.50    0.26    --  117.50-125.00-180.00  128
 18  ω     47.00 111.00   0.50    0.26    --  117.50-125.00-180.00  128
 19  ω     45.00 105.00   0.50    0.26    --  117.50 -95.00-180.00  120
 20  ω     45.00 105.00   0.50    0.26    --  117.50 -95.00-120.00  120
 21  ω     45.00 105.00   0.50    0.26    --  117.50 -95.00 -90.00  120
 22  ω     45.00 105.00   0.50    0.26    --  117.50 -95.00 -60.00  120
 23  ω     45.00 105.00   0.50    0.26    --  117.50 -95.00 -30.00  120
 24  ω     45.00 105.00   0.50    0.26    --  117.50 -95.00   0.00  120
 25  ω     45.00 105.00   0.50    0.26    --  117.50 -95.00  60.00  120
 26  ω     45.00 105.00   0.50    0.26    --  117.50 -95.00 150.00  120
 27  ω     67.00  93.00   0.50    0.26    --  117.50 -95.00  90.00   52
 28  ω     45.00 150.00   0.50    0.26    --  117.50 -88.00 -91.03  210
 29  ω     45.00 149.00   0.50    0.26    --  117.50 -87.00-170.29  208
 30  ω     45.00 149.00   0.50    0.26    --  117.50 -87.00-170.29  208
 31  ω    122.00 147.00   0.50    0.26    --  117.50 -87.00-170.29   50
 32  ω     87.00 113.00   0.50    0.26    --  117.50 -84.00-152.48   52
 33  ω     89.00 115.00   0.50    0.26    --  117.50 -88.00 -91.03   52
 34  ω     45.00 105.00   0.50    0.26    --  117.50 -77.00   0.00  120
 35  ω     45.00 105.00   0.50    0.26    --  117.50 -77.00 -60.00  120
 36  ω     45.00 105.00   0.50    0.26    --  117.50 -77.00-150.00  120
 37  ω     45.00 105.00   0.50    0.26    --  117.50 -77.00-120.00  120
 38  ω     77.00 103.00   0.50    0.26    --  117.50 -77.00 -90.00   52
 39  ω     45.00  71.00   0.50    0.26    --  117.50 -61.00 -30.00   52
 40  ω     45.00  71.00   0.50    0.26    --  117.50 -61.00  30.00   52
 41  ω     45.00  71.00   0.50    0.26    --  117.50 -61.00  60.00   52
 42  ω     55.00 105.00   0.50    0.26    --  117.50 -77.00  60.00  100
 43  ω     64.00  90.00   0.50    0.26    --  117.50  -1.00 167.79   52
 44  ω     45.00  71.00   0.50    0.26    --  117.50 -61.00 120.00   52
 45  ω     45.00 105.00   0.50    0.26    --  117.50 -77.00 150.00  120
 46  ω     45.00 105.00   0.50    0.26    --  117.50 -77.00 120.00  120
 47  ω     45.00  70.00   0.50    0.26    --  117.50 -61.00 -90.00   50
 48  ω     86.00 178.00   0.50    0.26    --  117.50  15.00 -90.00  184
 49  ω     91.00 178.00   0.50    0.26    --  117.50  77.00-150.00  174
 50  ω     91.00 178.00   0.50    0.26    --  117.50  77.00 -30.00  174
 51  ω     91.00 178.00   0.50    0.26    --  117.50  77.00 -30.00  174
 52  ω    120.00 146.00   0.50    0.26    --  117.50  61.00 -30.00   52
 53  ω     98.00 178.00   0.50    0.26    --  117.50  45.00   0.00  160
 54  ω     91.00 178.00   0.50    0.26    --  117.50  77.00  90.00  174
 55  ω    109.00 135.00   0.50    0.26    --  117.50  45.00 150.00   52
 56  ω     17.00 118.00   0.50    0.06    --   44.12  77.00 -60.00  202
 57  ω     17.00 118.00   0.50    0.06    --   44.12  77.00 -60.00  202
 58  ω    101.00 159.00   0.50    0.26    --  117.50  45.00-180.00  116
 59  ω     98.00 178.00   0.50    0.26    --  117.50  30.00-150.00  160
 60  ω     98.00 178.00   0.50    0.26    --  117.50  30.00 -90.00  160
 61  ω     98.00 178.00   0.50    0.26    --  117.50  45.00 -60.00  160
 62  ω    113.00 139.00   0.50    0.26    --  117.50  30.00   0.00   52
 63  ω     87.00 113.00   0.50    0.26    --  117.50  15.00 -90.00   52
 64  ω     86.00 178.00   0.50    0.26    --  117.50  15.00  30.00  184
 65  ω    104.00 163.00   0.50    0.26    --  117.50  30.00  90.00  118
 66  ω     86.00 178.00   0.50    0.26    --  117.50  15.00 150.00  184
 67  ω     95.00 178.00   0.50    0.26    --  117.50 125.00 120.00  166
 68  ω    102.00 178.00   0.50    0.26    --  117.50 114.00 151.00  152
 69  ω     95.00 178.00   0.50    0.26    --  117.50 125.00 150.00  166
 70  ω    128.00 154.00   0.50    0.26    --  117.50 125.00 120.00   52
 71  ω    -27.00  35.00   0.50    0.06    --  -44.12  19.00-180.00  124
 72  ω    -43.00  32.00   0.50    0.06    --  -44.12  38.00  60.00  150
 73  ω    -83.00 -26.00   0.50    0.26    --  -96.00 114.00 151.00  114
 74  ω    -83.00  -5.00   0.50    0.06    --  -44.12 114.00 151.00  156
 75  ω    -51.00 -21.00   0.50    0.26    --  -96.00  45.00  90.00   60
 76  ω   -170.00 -76.00   0.50    0.26    --  -96.00 -54.00 126.35  188
 77  ω   -166.00 -80.00   0.50    0.26    --  -96.00-114.00  60.00  172
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  '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      -0.1706631000
_diffrn_orient_matrix_UB_12      0.0795279000
_diffrn_orient_matrix_UB_13      0.0335374000
_diffrn_orient_matrix_UB_21      -0.0271132000
_diffrn_orient_matrix_UB_22      0.0492063000
_diffrn_orient_matrix_UB_23      -0.1159985000
_diffrn_orient_matrix_UB_31      -0.0865163000
_diffrn_orient_matrix_UB_32      -0.1512689000
_diffrn_orient_matrix_UB_33      0.0209869000
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3900
_reflns_number_total             4029
_reflns_odcompleteness_completeness 97.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     81.42
_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 1.171.43.124a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.124a 64-bit (release 23-05-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.124a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         4029
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0316
_refine_ls_R_factor_gt           0.0310
_refine_ls_restrained_S_all      1.083
_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)+(0.0352P)²+0.5261P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0798
_refine_ls_wR_factor_ref         0.0802
_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. Rigid bond restraints
 S6, C6
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
3.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C17(H17A,H17B)
3.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C12(H12), C13(H13), C14(H14), C20(H20), C21(H21),
 C22(H22), C23(H23), C24(H24)
3.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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 0.65051(4) 0.73195(4) 0.55963(2) 0.01536(9) Uani 1 1 d . . . . .
S6 S 0.93365(4) 0.29318(4) 0.75856(3) 0.02199(9) Uani 1 1 d . U . . .
O2 O 0.84957(12) 0.95658(11) 0.44474(8) 0.0207(2) Uani 1 1 d . . . . .
N3 N 0.84994(14) 0.87091(12) 0.62416(8) 0.0148(2) Uani 1 1 d . . . . .
H3 H 0.933(3) 0.926(2) 0.6173(15) 0.023(4) Uiso 1 1 d . . . . .
N5 N 0.92715(13) 0.60347(12) 0.70602(9) 0.0145(2) Uani 1 1 d . . . . .
N7 N 0.67595(13) 0.50927(12) 0.74794(9) 0.0149(2) Uani 1 1 d . . . . .
C2 C 0.80136(16) 0.87179(15) 0.53326(10) 0.0153(2) Uani 1 1 d . . . . .
C4 C 0.81244(15) 0.73741(14) 0.71432(10) 0.0132(2) Uani 1 1 d . . . . .
C6 C 0.84531(16) 0.47168(15) 0.73583(10) 0.0153(2) Uani 1 1 d . U . . .
C8 C 0.64399(15) 0.67450(14) 0.70671(10) 0.0132(2) Uani 1 1 d . . . . .
C9 C 0.80458(15) 0.77239(14) 0.81920(10) 0.0138(2) Uani 1 1 d . . . . .
C10 C 0.74667(17) 0.91708(15) 0.83169(11) 0.0176(3) Uani 1 1 d . . . . .
H10 H 0.722251 0.998602 0.772290 0.021 Uiso 1 1 calc R U . . .
C11 C 0.72462(18) 0.94216(16) 0.93111(11) 0.0206(3) Uani 1 1 d . . . . .
H11 H 0.685075 1.040930 0.939288 0.025 Uiso 1 1 calc R U . . .
C12 C 0.75995(17) 0.82397(16) 1.01838(11) 0.0198(3) Uani 1 1 d . . . . .
H12 H 0.743047 0.841260 1.086314 0.024 Uiso 1 1 calc R U . . .
C13 C 0.82026(17) 0.68000(16) 1.00602(11) 0.0186(3) Uani 1 1 d . . . . .
H13 H 0.846044 0.599182 1.065406 0.022 Uiso 1 1 calc R U . . .
C14 C 0.84274(16) 0.65441(15) 0.90711(10) 0.0158(2) Uani 1 1 d . . . . .
H14 H 0.884354 0.556048 0.898975 0.019 Uiso 1 1 calc R U . . .
C15 C 1.10853(16) 0.61230(16) 0.68966(11) 0.0186(3) Uani 1 1 d . . . . .
H15A H 1.156567 0.516405 0.734246 0.022 Uiso 1 1 calc R U . . .
H15B H 1.133835 0.699893 0.712410 0.022 Uiso 1 1 calc R U . . .
C16 C 1.18969(18) 0.63366(18) 0.57396(12) 0.0248(3) Uani 1 1 d . . . . .
H16A H 1.140805 0.727484 0.529496 0.037 Uiso 1 1 calc R U . . .
H16B H 1.170073 0.544303 0.552356 0.037 Uiso 1 1 calc R U . . .
H16C H 1.310630 0.642994 0.565278 0.037 Uiso 1 1 calc R U . . .
C17 C 0.55053(17) 0.39564(15) 0.76699(11) 0.0178(3) Uani 1 1 d . . . . .
H17A H 0.438822 0.441074 0.791229 0.021 Uiso 1 1 calc R U . . .
H17B H 0.574916 0.304496 0.825513 0.021 Uiso 1 1 calc R U . . .
C18 C 0.54214(19) 0.34143(17) 0.67138(12) 0.0235(3) Uani 1 1 d . . . . .
H18A H 0.515038 0.430118 0.613320 0.035 Uiso 1 1 calc R U . . .
H18B H 0.455131 0.266491 0.691282 0.035 Uiso 1 1 calc R U . . .
H18C H 0.650840 0.292793 0.647963 0.035 Uiso 1 1 calc R U . . .
C19 C 0.48652(15) 0.73837(14) 0.76650(10) 0.0139(2) Uani 1 1 d . . . . .
C20 C 0.39951(16) 0.87286(15) 0.71809(10) 0.0167(2) Uani 1 1 d . . . . .
H20 H 0.433416 0.922464 0.644391 0.020 Uiso 1 1 calc R U . . .
C21 C 0.26278(17) 0.93528(16) 0.77715(11) 0.0192(3) Uani 1 1 d . . . . .
H21 H 0.204249 1.027040 0.743562 0.023 Uiso 1 1 calc R U . . .
C22 C 0.21244(16) 0.86335(16) 0.88481(11) 0.0195(3) Uani 1 1 d . . . . .
H22 H 0.118641 0.904985 0.924822 0.023 Uiso 1 1 calc R U . . .
C23 C 0.29985(17) 0.72998(16) 0.93397(11) 0.0191(3) Uani 1 1 d . . . . .
H23 H 0.266291 0.681338 1.007852 0.023 Uiso 1 1 calc R U . . .
C24 C 0.43590(16) 0.66764(15) 0.87559(10) 0.0164(2) Uani 1 1 d . . . . .
H24 H 0.494948 0.576617 0.909742 0.020 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C2 1.7772(13) . ?
S1 C8 1.8735(12) . ?
S6 C6 1.6674(13) . ?
O2 C2 1.2170(16) . ?
N3 H3 0.86(2) . ?
N3 C2 1.3565(17) . ?
N3 C4 1.4408(16) . ?
N5 C4 1.4680(16) . ?
N5 C6 1.3502(17) . ?
N5 C15 1.4585(16) . ?
N7 C6 1.3741(17) . ?
N7 C8 1.4509(16) . ?
N7 C17 1.4667(16) . ?
C4 C8 1.5812(16) . ?
C4 C9 1.5201(17) . ?
C8 C19 1.5210(17) . ?
C9 C10 1.3939(18) . ?
C9 C14 1.3990(18) . ?
C10 H10 0.9500 . ?
C10 C11 1.3912(19) . ?
C11 H11 0.9500 . ?
C11 C12 1.387(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.391(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.3862(18) . ?
C14 H14 0.9500 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.5171(19) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.5221(19) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.3939(18) . ?
C19 C24 1.4021(18) . ?
C20 H20 0.9500 . ?
C20 C21 1.3976(19) . ?
C21 H21 0.9500 . ?
C21 C22 1.388(2) . ?
C22 H22 0.9500 . ?
C22 C23 1.392(2) . ?
C23 H23 0.9500 . ?
C23 C24 1.3890(19) . ?
C24 H24 0.9500 . ?

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
C2 S1 C8 93.18(6) . . ?
C2 N3 H3 116.7(13) . . ?
C2 N3 C4 116.86(11) . . ?
C4 N3 H3 121.1(13) . . ?
C6 N5 C4 112.02(10) . . ?
C6 N5 C15 125.21(11) . . ?
C15 N5 C4 121.52(10) . . ?
C6 N7 C8 110.84(10) . . ?
C6 N7 C17 122.81(11) . . ?
C8 N7 C17 123.61(10) . . ?
O2 C2 S1 122.97(10) . . ?
O2 C2 N3 126.25(12) . . ?
N3 C2 S1 110.78(9) . . ?
N3 C4 N5 112.64(10) . . ?
N3 C4 C8 107.55(10) . . ?
N3 C4 C9 112.21(10) . . ?
N5 C4 C8 99.50(9) . . ?
N5 C4 C9 111.29(10) . . ?
C9 C4 C8 112.98(10) . . ?
N5 C6 S6 126.01(10) . . ?
N5 C6 N7 108.33(11) . . ?
N7 C6 S6 125.62(10) . . ?
N7 C8 S1 111.13(8) . . ?
N7 C8 C4 101.21(9) . . ?
N7 C8 C19 114.12(10) . . ?
C4 C8 S1 102.39(8) . . ?
C19 C8 S1 112.64(8) . . ?
C19 C8 C4 114.24(10) . . ?
C10 C9 C4 120.94(11) . . ?
C10 C9 C14 119.23(12) . . ?
C14 C9 C4 119.62(11) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 C9 120.03(12) . . ?
C11 C10 H10 120.0 . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.47(13) . . ?
C12 C11 H11 119.8 . . ?
C11 C12 H12 120.1 . . ?
C11 C12 C13 119.74(12) . . ?
C13 C12 H12 120.1 . . ?
C12 C13 H13 120.0 . . ?
C14 C13 C12 120.04(12) . . ?
C14 C13 H13 120.0 . . ?
C9 C14 H14 119.8 . . ?
C13 C14 C9 120.47(12) . . ?
C13 C14 H14 119.8 . . ?
N5 C15 H15A 109.3 . . ?
N5 C15 H15B 109.3 . . ?
N5 C15 C16 111.57(11) . . ?
H15A C15 H15B 108.0 . . ?
C16 C15 H15A 109.3 . . ?
C16 C15 H15B 109.3 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N7 C17 H17A 108.5 . . ?
N7 C17 H17B 108.5 . . ?
N7 C17 C18 115.15(11) . . ?
H17A C17 H17B 107.5 . . ?
C18 C17 H17A 108.5 . . ?
C18 C17 H17B 108.5 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 C8 121.80(11) . . ?
C20 C19 C24 118.98(12) . . ?
C24 C19 C8 118.99(11) . . ?
C19 C20 H20 119.7 . . ?
C19 C20 C21 120.50(12) . . ?
C21 C20 H20 119.7 . . ?
C20 C21 H21 120.0 . . ?
C22 C21 C20 120.07(12) . . ?
C22 C21 H21 120.0 . . ?
C21 C22 H22 120.1 . . ?
C21 C22 C23 119.76(12) . . ?
C23 C22 H22 120.1 . . ?
C22 C23 H23 119.8 . . ?
C24 C23 C22 120.35(13) . . ?
C24 C23 H23 119.8 . . ?
C19 C24 H24 119.8 . . ?
C23 C24 C19 120.33(12) . . ?
C23 C24 H24 119.8 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N3 H3 O2 0.86(2) 2.06(2) 2.8944(15) 162.0(17) 2_776 yes

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 C8 C19 C20 -26.29(15) . . . . ?
S1 C8 C19 C24 159.33(10) . . . . ?
N3 C4 C8 S1 29.58(11) . . . . ?
N3 C4 C8 N7 144.40(10) . . . . ?
N3 C4 C8 C19 -92.50(12) . . . . ?
N3 C4 C9 C10 33.18(16) . . . . ?
N3 C4 C9 C14 -152.14(11) . . . . ?
N5 C4 C8 S1 -87.96(9) . . . . ?
N5 C4 C8 N7 26.86(11) . . . . ?
N5 C4 C8 C19 149.96(10) . . . . ?
N5 C4 C9 C10 160.43(11) . . . . ?
N5 C4 C9 C14 -24.89(16) . . . . ?
N7 C8 C19 C20 -154.21(12) . . . . ?
N7 C8 C19 C24 31.41(16) . . . . ?
C2 S1 C8 N7 -125.95(9) . . . . ?
C2 S1 C8 C4 -18.60(8) . . . . ?
C2 S1 C8 C19 104.57(9) . . . . ?
C2 N3 C4 N5 76.88(14) . . . . ?
C2 N3 C4 C8 -31.75(14) . . . . ?
C2 N3 C4 C9 -156.60(11) . . . . ?
C4 N3 C2 S1 16.77(14) . . . . ?
C4 N3 C2 O2 -164.35(12) . . . . ?
C4 N5 C6 S6 -168.05(9) . . . . ?
C4 N5 C6 N7 9.86(14) . . . . ?
C4 N5 C15 C16 -99.79(14) . . . . ?
C4 C8 C19 C20 89.99(14) . . . . ?
C4 C8 C19 C24 -84.39(14) . . . . ?
C4 C9 C10 C11 173.59(12) . . . . ?
C4 C9 C14 C13 -173.55(11) . . . . ?
C6 N5 C4 N3 -137.06(11) . . . . ?
C6 N5 C4 C8 -23.42(13) . . . . ?
C6 N5 C4 C9 95.93(12) . . . . ?
C6 N5 C15 C16 94.07(15) . . . . ?
C6 N7 C8 S1 84.16(11) . . . . ?
C6 N7 C8 C4 -23.97(13) . . . . ?
C6 N7 C8 C19 -147.15(11) . . . . ?
C6 N7 C17 C18 -72.58(16) . . . . ?
C8 S1 C2 O2 -175.90(12) . . . . ?
C8 S1 C2 N3 3.03(10) . . . . ?
C8 N7 C6 S6 -171.70(9) . . . . ?
C8 N7 C6 N5 10.37(14) . . . . ?
C8 N7 C17 C18 86.93(15) . . . . ?
C8 C4 C9 C10 -88.61(14) . . . . ?
C8 C4 C9 C14 86.07(14) . . . . ?
C8 C19 C20 C21 -175.07(12) . . . . ?
C8 C19 C24 C23 175.29(12) . . . . ?
C9 C4 C8 S1 153.96(9) . . . . ?
C9 C4 C8 N7 -91.22(11) . . . . ?
C9 C4 C8 C19 31.88(14) . . . . ?
C9 C10 C11 C12 0.0(2) . . . . ?
C10 C9 C14 C13 1.22(19) . . . . ?
C10 C11 C12 C13 1.0(2) . . . . ?
C11 C12 C13 C14 -0.9(2) . . . . ?
C12 C13 C14 C9 -0.2(2) . . . . ?
C14 C9 C10 C11 -1.11(19) . . . . ?
C15 N5 C4 N3 55.13(15) . . . . ?
C15 N5 C4 C8 168.78(11) . . . . ?
C15 N5 C4 C9 -71.88(14) . . . . ?
C15 N5 C6 S6 -0.78(19) . . . . ?
C15 N5 C6 N7 177.13(11) . . . . ?
C17 N7 C6 S6 -9.88(18) . . . . ?
C17 N7 C6 N5 172.19(11) . . . . ?
C17 N7 C8 S1 -77.49(13) . . . . ?
C17 N7 C8 C4 174.38(11) . . . . ?
C17 N7 C8 C19 51.20(15) . . . . ?
C19 C20 C21 C22 -0.1(2) . . . . ?
C20 C19 C24 C23 0.75(19) . . . . ?
C20 C21 C22 C23 0.8(2) . . . . ?
C21 C22 C23 C24 -0.7(2) . . . . ?
C22 C23 C24 C19 0.0(2) . . . . ?
C24 C19 C20 C21 -0.69(19) . . . . ?

_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 1.183
_oxdiff_exptl_absorpt_empirical_full_min 0.792
####################################################################### 
# 
# 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_3j
_database_code_depnum_ccdc_archive 'CCDC 2444502'
loop_
_audit_author_name
_audit_author_address
'Victor Khrustalev'
;Peoples Friendship University of Russia (RUDN University, Moscow)
Russia
;
_audit_update_record             
;
2025-04-16 deposited with the CCDC.	2025-07-01 downloaded from the CCDC.
;
_audit_creation_date             2023-04-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.11.18 svn.ra9532c28 for OlexSys, GUI svn.r6429)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H21 N3 O4 S'
_chemical_formula_sum            'C20 H21 N3 O4 S'
_chemical_formula_weight         399.46
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H21N3O4S
_chemical_oxdiff_usercomment     C3636-2
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.78910(10)
_cell_length_b                   10.34730(10)
_cell_length_c                   21.3735(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.3510(10)
_cell_angle_gamma                90
_cell_volume                     1940.46(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    20314
_cell_measurement_temperature    99.9(2)
_cell_measurement_theta_max      77.5070
_cell_measurement_theta_min      4.1250
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.756
_exptl_absorpt_correction_T_max  0.17740
_exptl_absorpt_correction_T_min  0.07369
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.79a (Rigaku Oxford Diffraction, 2022)
Spherical absorption correction
using equivalent radius and absorption coefficient.
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_crystal_size_rad          0.160
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            26362
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.740
_diffrn_reflns_theta_min         4.144
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(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 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -79.00 -14.00   0.50    0.60    --  -86.25  95.00 -30.00  130
  2  ω    -79.00  24.00   0.50    0.20    --  -48.70  95.00 -30.00  206
  3  ω     -6.00  23.00   0.50    0.20    --  -48.70  19.00  60.00   58
  4  ω    -32.00  24.00   0.50    0.20    --  -48.70  38.00  90.00  112
  5  ω    110.00 144.00   0.50    0.60    --  107.75  77.00   0.00   68
  6  ω     97.00 125.00   0.50    0.60    --  107.75  61.00 -60.00   56
  7  ω     98.00 124.00   0.50    0.60    --  107.75  61.00 -90.00   52
  8  ω    108.00 134.00   0.50    0.60    --  107.75  61.00-180.00   52
  9  ω    133.00 166.00   0.50    0.60    --  107.75  61.00 -90.00   66
 10  ω    140.00 175.00   0.50    0.60    --  107.75  61.00 -60.00   70
 11  ω     98.00 139.00   0.50    0.60    --  107.75  30.00 -90.00   82
 12  ω    115.00 141.00   0.50    0.60    --  107.75  15.00 -90.00   52
 13  ω     86.00 170.00   0.50    0.60    --  107.75  77.00  30.00  168
 14  ω    143.00 178.00   0.50    0.60    --  107.75  45.00  60.00   70
 15  ω    146.00 171.00   0.50    0.60    --  107.75  30.00 120.00   50
 16  ω    105.00 130.00   0.50    0.60    --  107.75  30.00 120.00   50
 17  ω    153.00 178.00   0.50    0.60    --  107.75  15.00 -90.00   50
 18  ω    134.00 178.00   0.50    0.60    --  107.75  15.00-180.00   88
 19  ω     97.00 153.00   0.50    0.60    --  107.75 125.00-120.00  112
 20  ω    105.00 178.00   0.50    0.60    --  107.75  95.00 -30.00  146
 21  ω    141.00 166.00   0.50    0.60    --  107.75 125.00  30.00   50
 22  ω     78.00 105.00   0.50    0.60    --  107.75 -77.00  30.00   54
 23  ω     49.00  75.00   0.50    0.60    --  107.75 -77.00  30.00   52
 24  ω     39.00  82.00   0.50    0.60    --  107.75 -77.00   0.00   86
 25  ω     52.00 105.00   0.50    0.60    --  107.75 -77.00-120.00  106
 26  ω     38.00  66.00   0.50    0.60    --  107.75 -77.00-180.00   56
 27  ω     36.00  61.00   0.50    0.60    --  107.75 -61.00-120.00   50
 28  ω     61.00 103.00   0.50    0.60    --  107.75 -77.00 -30.00   84
 29  ω     77.00 123.00   0.50    0.60    --  107.75-140.00  67.61   92
 30  ω     79.00 111.00   0.50    0.60    --  107.75-125.00  90.00   64
 31  ω     39.00  64.00   0.50    0.60    --  107.75-125.00  90.00   50
 32  ω     39.00  65.00   0.50    0.60    --  107.75-125.00 150.00   52
 33  ω     81.00 107.00   0.50    0.60    --  107.75-100.00  69.96   52
 34  ω     39.00  69.00   0.50    0.60    --  107.75-125.00  30.00   60
 35  ω     55.00  81.00   0.50    0.60    --  107.75-125.00   0.00   52
 36  ω     43.00  87.00   0.50    0.60    --  107.75-136.00-125.77   88
 37  ω     72.00  97.00   0.50    0.60    --  107.75 -95.00-180.00   50
 38  ω     36.00 105.00   0.50    0.60    --  107.75 -95.00-140.00  138
 39  ω     43.00  69.00   0.50    0.60    --  107.75 -95.00 -90.00   52
 40  ω    108.00 134.00   0.50    0.60    --  107.75 -88.00-135.34   52
 41  ω     85.00 111.00   0.50    0.60    --  107.75 -87.00-104.95   52
 42  ω     99.00 132.00   0.50    0.60    --  107.75 -83.00-115.51   66
 43  ω     39.00  75.00   0.50    0.60    --  107.75 -88.00-135.34   72
 44  ω     99.00 129.00   0.50    0.60    --  107.75 -82.00 165.92   60
 45  ω     36.00  86.00   0.50    0.60    --  107.75 -82.00 165.92  100
 46  ω     43.00  72.00   0.50    0.60    --  107.75 -95.00 150.00   58
 47  ω     -9.00  79.00   0.50    0.20    --   48.70 -95.00-140.00  176
 48  ω   -158.00 -83.00   0.50    0.60    --  -86.25 -95.00-140.00  150
 49  ω   -100.00 -74.00   0.50    0.20    --  -48.70-125.00 -90.00   52
 50  ω   -105.00 -79.00   0.50    0.20    --  -48.70-125.00   0.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  '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      0.0417072000
_diffrn_orient_matrix_UB_12      0.0109169000
_diffrn_orient_matrix_UB_13      0.0708326000
_diffrn_orient_matrix_UB_21      -0.0585921000
_diffrn_orient_matrix_UB_22      -0.1385199000
_diffrn_orient_matrix_UB_23      0.0095455000
_diffrn_orient_matrix_UB_31      0.1601777000
_diffrn_orient_matrix_UB_32      -0.0534453000
_diffrn_orient_matrix_UB_33      -0.0102851000
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4009
_reflns_number_total             4133
_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 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.364
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         4133
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0408
_refine_ls_restrained_S_all      1.046
_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)+(0.0665P)²+0.6603P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1151
_refine_ls_wR_factor_ref         0.1158
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C6(H6), C7(H7), C9(H9), C10(H10), C15(H15), C16(H16), C18(H18),
 C19(H19)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C20(H20A,H20B,
 H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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 0.65109(4) 0.60558(4) 0.25275(2) 0.04009(13) Uani 1 1 d . . . . .
O1 O 0.62615(16) 0.45765(13) 0.15147(5) 0.0534(3) Uani 1 1 d . . . . .
O2 O 0.36253(13) 0.00423(11) 0.45351(5) 0.0434(3) Uani 1 1 d . . . . .
O3 O 0.22144(13) 0.71356(11) 0.32180(5) 0.0418(3) Uani 1 1 d . . . . .
O4 O 0.97905(12) 0.28654(12) 0.49461(5) 0.0436(3) Uani 1 1 d . . . . .
N1 N 0.49739(14) 0.39329(12) 0.23589(6) 0.0359(3) Uani 1 1 d . . . . .
H1 H 0.471414 0.316831 0.220735 0.043 Uiso 1 1 calc R U . . .
N2 N 0.30746(13) 0.51703(12) 0.28728(6) 0.0345(3) Uani 1 1 d . . . . .
N3 N 0.46335(14) 0.63570(12) 0.34943(6) 0.0369(3) Uani 1 1 d . . . . .
C1 C 0.58757(19) 0.47268(16) 0.20444(7) 0.0417(3) Uani 1 1 d . . . . .
C2 C 0.44399(15) 0.43699(14) 0.29551(6) 0.0327(3) Uani 1 1 d . . . . .
C3 C 0.31983(17) 0.63031(14) 0.31887(7) 0.0362(3) Uani 1 1 d . . . . .
C4 C 0.56235(16) 0.54069(14) 0.32357(7) 0.0343(3) Uani 1 1 d . . . . .
C5 C 0.42112(15) 0.32368(14) 0.33915(6) 0.0321(3) Uani 1 1 d . . . . .
C6 C 0.51572(16) 0.21531(14) 0.33817(7) 0.0353(3) Uani 1 1 d . . . . .
H6 H 0.594138 0.212316 0.309442 0.042 Uiso 1 1 calc R U . . .
C7 C 0.49743(17) 0.11278(14) 0.37808(7) 0.0375(3) Uani 1 1 d . . . . .
H7 H 0.564597 0.040917 0.377472 0.045 Uiso 1 1 calc R U . . .
C8 C 0.38013(17) 0.11431(14) 0.41947(7) 0.0365(3) Uani 1 1 d . . . . .
C9 C 0.28942(16) 0.22323(15) 0.42329(7) 0.0360(3) Uani 1 1 d . . . . .
H9 H 0.213112 0.227117 0.452934 0.043 Uiso 1 1 calc R U . . .
C10 C 0.31122(16) 0.32705(14) 0.38321(7) 0.0338(3) Uani 1 1 d . . . . .
H10 H 0.249399 0.401883 0.386119 0.041 Uiso 1 1 calc R U . . .
C11 C 0.2430(2) 0.00292(18) 0.49584(8) 0.0503(4) Uani 1 1 d . . . . .
H11A H 0.240844 -0.081216 0.516825 0.075 Uiso 1 1 calc R U . . .
H11B H 0.145186 0.017924 0.472566 0.075 Uiso 1 1 calc R U . . .
H11C H 0.260768 0.071150 0.527219 0.075 Uiso 1 1 calc R U . . .
C12 C 0.16666(17) 0.47092(16) 0.25613(7) 0.0401(3) Uani 1 1 d . . . . .
H12A H 0.085443 0.534096 0.261627 0.060 Uiso 1 1 calc R U . . .
H12B H 0.138504 0.388040 0.274395 0.060 Uiso 1 1 calc R U . . .
H12C H 0.180942 0.459500 0.211338 0.060 Uiso 1 1 calc R U . . .
C13 C 0.5250(2) 0.76023(16) 0.37039(8) 0.0457(4) Uani 1 1 d . . . . .
H13A H 0.604092 0.746648 0.403982 0.068 Uiso 1 1 calc R U . . .
H13B H 0.443098 0.813310 0.386081 0.068 Uiso 1 1 calc R U . . .
H13C H 0.569191 0.804421 0.335183 0.068 Uiso 1 1 calc R U . . .
C14 C 0.68051(16) 0.48535(14) 0.37050(7) 0.0341(3) Uani 1 1 d . . . . .
C15 C 0.80325(16) 0.41318(15) 0.35055(7) 0.0365(3) Uani 1 1 d . . . . .
H15 H 0.820810 0.409495 0.307145 0.044 Uiso 1 1 calc R U . . .
C16 C 0.89908(17) 0.34737(16) 0.39272(7) 0.0386(3) Uani 1 1 d . . . . .
H16 H 0.980116 0.296951 0.378142 0.046 Uiso 1 1 calc R U . . .
C17 C 0.87754(17) 0.35449(15) 0.45681(7) 0.0374(3) Uani 1 1 d . . . . .
C18 C 0.75698(18) 0.42690(16) 0.47768(7) 0.0393(3) Uani 1 1 d . . . . .
H18 H 0.741834 0.433120 0.521228 0.047 Uiso 1 1 calc R U . . .
C19 C 0.65894(17) 0.49002(15) 0.43440(7) 0.0375(3) Uani 1 1 d . . . . .
H19 H 0.575284 0.537437 0.448796 0.045 Uiso 1 1 calc R U . . .
C20 C 0.9611(2) 0.29180(19) 0.56091(8) 0.0488(4) Uani 1 1 d . . . . .
H20A H 1.035818 0.234509 0.582533 0.073 Uiso 1 1 calc R U . . .
H20B H 0.857970 0.263882 0.569669 0.073 Uiso 1 1 calc R U . . .
H20C H 0.977377 0.380601 0.575787 0.073 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.7893(17) . ?
S1 C4 1.8676(14) . ?
O1 C1 1.211(2) . ?
O2 C8 1.3652(18) . ?
O2 C11 1.426(2) . ?
O3 C3 1.2248(18) . ?
O4 C17 1.3634(19) . ?
O4 C20 1.4359(19) . ?
N1 H1 0.8800 . ?
N1 C1 1.348(2) . ?
N1 C2 1.4554(18) . ?
N2 C2 1.4602(18) . ?
N2 C3 1.354(2) . ?
N2 C12 1.4512(19) . ?
N3 C3 1.387(2) . ?
N3 C4 1.4441(19) . ?
N3 C13 1.4580(19) . ?
C2 C4 1.5876(19) . ?
C2 C5 1.5188(19) . ?
C4 C14 1.514(2) . ?
C5 C6 1.397(2) . ?
C5 C10 1.388(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.377(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.397(2) . ?
C8 C9 1.386(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.394(2) . ?
C10 H10 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.399(2) . ?
C14 C19 1.391(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.377(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.396(2) . ?
C17 C18 1.392(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.390(2) . ?
C19 H19 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?

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
C1 S1 C4 93.47(7) . . ?
C8 O2 C11 117.17(13) . . ?
C17 O4 C20 117.36(13) . . ?
C1 N1 H1 120.8 . . ?
C1 N1 C2 118.45(12) . . ?
C2 N1 H1 120.8 . . ?
C3 N2 C2 112.93(12) . . ?
C3 N2 C12 123.70(13) . . ?
C12 N2 C2 122.79(12) . . ?
C3 N3 C4 110.12(12) . . ?
C3 N3 C13 119.44(13) . . ?
C4 N3 C13 119.86(13) . . ?
O1 C1 S1 122.92(13) . . ?
O1 C1 N1 126.37(15) . . ?
N1 C1 S1 110.68(11) . . ?
N1 C2 N2 112.06(11) . . ?
N1 C2 C4 107.64(11) . . ?
N1 C2 C5 111.03(12) . . ?
N2 C2 C4 100.25(11) . . ?
N2 C2 C5 111.99(11) . . ?
C5 C2 C4 113.40(11) . . ?
O3 C3 N2 126.73(14) . . ?
O3 C3 N3 124.95(14) . . ?
N2 C3 N3 108.29(12) . . ?
N3 C4 S1 110.79(10) . . ?
N3 C4 C2 102.04(11) . . ?
N3 C4 C14 114.17(12) . . ?
C2 C4 S1 103.43(9) . . ?
C14 C4 S1 111.73(10) . . ?
C14 C4 C2 113.81(12) . . ?
C6 C5 C2 120.68(12) . . ?
C10 C5 C2 121.29(13) . . ?
C10 C5 C6 117.95(13) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 C5 121.22(14) . . ?
C7 C6 H6 119.4 . . ?
C6 C7 H7 120.0 . . ?
C6 C7 C8 120.05(13) . . ?
C8 C7 H7 120.0 . . ?
O2 C8 C7 116.02(13) . . ?
O2 C8 C9 124.31(14) . . ?
C9 C8 C7 119.66(13) . . ?
C8 C9 H9 120.3 . . ?
C8 C9 C10 119.36(14) . . ?
C10 C9 H9 120.3 . . ?
C5 C10 C9 121.56(13) . . ?
C5 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
O2 C11 H11A 109.5 . . ?
O2 C11 H11B 109.5 . . ?
O2 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 H12A 109.5 . . ?
N2 C12 H12B 109.5 . . ?
N2 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N3 C13 H13A 109.5 . . ?
N3 C13 H13B 109.5 . . ?
N3 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C4 120.76(13) . . ?
C19 C14 C4 120.67(13) . . ?
C19 C14 C15 118.02(14) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 C14 121.16(14) . . ?
C16 C15 H15 119.4 . . ?
C15 C16 H16 119.9 . . ?
C15 C16 C17 120.23(14) . . ?
C17 C16 H16 119.9 . . ?
O4 C17 C16 115.65(14) . . ?
O4 C17 C18 124.85(14) . . ?
C18 C17 C16 119.49(14) . . ?
C17 C18 H18 120.2 . . ?
C19 C18 C17 119.57(14) . . ?
C19 C18 H18 120.2 . . ?
C14 C19 H19 119.2 . . ?
C18 C19 C14 121.51(14) . . ?
C18 C19 H19 119.2 . . ?
O4 C20 H20A 109.5 . . ?
O4 C20 H20B 109.5 . . ?
O4 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 O3 0.88 2.16 2.8985(16) 141.3 2_545 yes

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 C4 C14 C15 -40.11(17) . . . . ?
S1 C4 C14 C19 148.59(12) . . . . ?
O2 C8 C9 C10 -175.69(13) . . . . ?
O4 C17 C18 C19 -178.68(14) . . . . ?
N1 C2 C4 S1 25.08(13) . . . . ?
N1 C2 C4 N3 140.17(12) . . . . ?
N1 C2 C4 C14 -96.35(13) . . . . ?
N1 C2 C5 C6 33.65(17) . . . . ?
N1 C2 C5 C10 -149.62(13) . . . . ?
N2 C2 C4 S1 -92.18(10) . . . . ?
N2 C2 C4 N3 22.92(13) . . . . ?
N2 C2 C4 C14 146.39(12) . . . . ?
N2 C2 C5 C6 159.75(12) . . . . ?
N2 C2 C5 C10 -23.52(18) . . . . ?
N3 C4 C14 C15 -166.82(13) . . . . ?
N3 C4 C14 C19 21.89(19) . . . . ?
C1 S1 C4 N3 -125.96(11) . . . . ?
C1 S1 C4 C2 -17.30(10) . . . . ?
C1 S1 C4 C14 105.52(11) . . . . ?
C1 N1 C2 N2 84.25(16) . . . . ?
C1 N1 C2 C4 -25.03(18) . . . . ?
C1 N1 C2 C5 -149.69(13) . . . . ?
C2 N1 C1 S1 11.31(18) . . . . ?
C2 N1 C1 O1 -170.57(16) . . . . ?
C2 N2 C3 O3 -177.62(14) . . . . ?
C2 N2 C3 N3 0.76(16) . . . . ?
C2 C4 C14 C15 76.58(16) . . . . ?
C2 C4 C14 C19 -94.71(16) . . . . ?
C2 C5 C6 C7 179.11(13) . . . . ?
C2 C5 C10 C9 179.84(13) . . . . ?
C3 N2 C2 N1 -129.13(13) . . . . ?
C3 N2 C2 C4 -15.21(14) . . . . ?
C3 N2 C2 C5 105.34(13) . . . . ?
C3 N3 C4 S1 84.90(12) . . . . ?
C3 N3 C4 C2 -24.67(15) . . . . ?
C3 N3 C4 C14 -147.91(12) . . . . ?
C4 S1 C1 O1 -173.10(16) . . . . ?
C4 S1 C1 N1 5.10(13) . . . . ?
C4 N3 C3 O3 -165.28(14) . . . . ?
C4 N3 C3 N2 16.30(16) . . . . ?
C4 C2 C5 C6 -87.68(16) . . . . ?
C4 C2 C5 C10 89.05(16) . . . . ?
C4 C14 C15 C16 -170.78(14) . . . . ?
C4 C14 C19 C18 172.49(14) . . . . ?
C5 C2 C4 S1 148.30(10) . . . . ?
C5 C2 C4 N3 -96.61(13) . . . . ?
C5 C2 C4 C14 26.87(16) . . . . ?
C5 C6 C7 C8 1.7(2) . . . . ?
C6 C5 C10 C9 -3.3(2) . . . . ?
C6 C7 C8 O2 174.69(13) . . . . ?
C6 C7 C8 C9 -4.6(2) . . . . ?
C7 C8 C9 C10 3.5(2) . . . . ?
C8 C9 C10 C5 0.5(2) . . . . ?
C10 C5 C6 C7 2.3(2) . . . . ?
C11 O2 C8 C7 -179.61(14) . . . . ?
C11 O2 C8 C9 -0.4(2) . . . . ?
C12 N2 C2 N1 59.35(17) . . . . ?
C12 N2 C2 C4 173.27(12) . . . . ?
C12 N2 C2 C5 -66.18(17) . . . . ?
C12 N2 C3 O3 -6.2(2) . . . . ?
C12 N2 C3 N3 172.19(13) . . . . ?
C13 N3 C3 O3 -20.6(2) . . . . ?
C13 N3 C3 N2 160.95(13) . . . . ?
C13 N3 C4 S1 -59.57(16) . . . . ?
C13 N3 C4 C2 -169.14(13) . . . . ?
C13 N3 C4 C14 67.62(17) . . . . ?
C14 C15 C16 C17 -1.7(2) . . . . ?
C15 C14 C19 C18 1.0(2) . . . . ?
C15 C16 C17 O4 -179.60(14) . . . . ?
C15 C16 C17 C18 1.0(2) . . . . ?
C16 C17 C18 C19 0.6(2) . . . . ?
C17 C18 C19 C14 -1.6(2) . . . . ?
C19 C14 C15 C16 0.7(2) . . . . ?
C20 O4 C17 C16 179.76(14) . . . . ?
C20 O4 C17 C18 -0.9(2) . . . . ?

_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 1.307
_oxdiff_exptl_absorpt_empirical_full_min 0.503
