#------------------------------------------------------------------------------
#$Date: 2025-08-06 01:32:30 +0300 (Wed, 06 Aug 2025) $
#$Revision: 301643 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/16/06/7160619.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7160619
loop_
_publ_author_name
'Ermolaev, Valery P.'
'Ratmanova, Nina K.'
'Baranov, Vladimir V.'
'Levina, Irina I.'
'Khrustalev, Victor N.'
'Ivanova, Olga A.'
'Kravchenko, Angelina N.'
'Trushkov, Igor V.'
'Andreev, Ivan A.'
_publ_section_title
;
 Multi-purpose thiocyanate protic ionic liquids in chemodivergent
 transformations of imidazolidin-2-(thi)one-based diols.
;
_journal_issue                   30
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              7157
_journal_page_last               7164
_journal_paper_doi               10.1039/d5ob00709g
_journal_volume                  23
_journal_year                    2025
_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
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2022-08-29
_audit_creation_method
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_audit_update_record
;
2025-04-16 deposited with the CCDC.	2025-07-01 downloaded from the CCDC.
;
_cell_angle_alpha                97.5406(8)
_cell_angle_beta                 97.5177(7)
_cell_angle_gamma                94.5922(7)
_cell_formula_units_Z            2
_cell_length_a                   8.20740(6)
_cell_length_b                   8.83930(8)
_cell_length_c                   17.27472(17)
_cell_measurement_reflns_used    45819
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      77.6300
_cell_measurement_theta_min      2.5660
_cell_volume                     1225.681(19)
_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)'
_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_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_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_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_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             524
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.053
_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_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0306
_refine_ls_R_factor_gt           0.0302
_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
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5112
_reflns_number_total             5196
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5ob00709g2.cif
_cod_data_source_block           2c
_cod_depositor_comments
'Adding full bibliography for 7160619--7160622.cif.'
_cod_database_code               7160619
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_chemical_oxdiff_usercomment     C3395
_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.
;
_shelx_estimated_absorpt_t_max   0.712
_shelx_estimated_absorpt_t_min   0.462
_reflns_odcompleteness_completeness 98.26
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     78.52
_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)
;
_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
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
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'
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
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_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_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) . . . . ?
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
