#------------------------------------------------------------------------------
#$Date: 2020-05-04 05:47:05 +0300 (Mon, 04 May 2020) $
#$Revision: 251481 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/82/4038261.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_4038261
loop_
_publ_author_name
'Galenko, Ekaterina E.'
'Kryukova, Mariya A.'
'Novikov, Mikhail S.'
'Khlebnikov, Alexander F.'
_publ_section_title
;
 Synthesis of Bi-, Ter-, and Quaterpyridinecarboxylates via
 Propargylisoxazole-Pyridine Rearrangement.
;
_journal_issue                   9
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6109
_journal_page_last               6122
_journal_paper_doi               10.1021/acs.joc.0c00611
_journal_volume                  85
_journal_year                    2020
_chemical_formula_moiety         'C27 H19 N3 O4 S'
_chemical_formula_sum            'C27 H19 N3 O4 S'
_chemical_formula_weight         481.51
_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   geom
_audit_creation_date             2020-02-28
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                107.6500(10)
_cell_angle_beta                 107.1590(10)
_cell_angle_gamma                93.5990(10)
_cell_formula_units_Z            2
_cell_length_a                   8.87440(10)
_cell_length_b                   11.65640(10)
_cell_length_c                   11.83170(10)
_cell_measurement_reflns_used    26193
_cell_measurement_temperature    100.01(12)
_cell_measurement_theta_max      76.6110
_cell_measurement_theta_min      4.0380
_cell_volume                     1098.70(2)
_computing_cell_refinement       'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(12)
_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 0.982
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -14.00  11.00   0.50    0.11    --   47.20 -21.00 -81.00   50
  2  ω     36.00  79.00   0.50    0.42    --  107.75 -77.00   0.00   86
  3  ω     57.00  97.00   0.50    0.42    --  107.75 -77.00  30.00   80
  4  ω     71.00 102.00   0.50    0.42    --  107.75-125.00 -60.00   62
  5  ω     81.00 106.00   0.50    0.42    --  107.75 -94.00-120.00   50
  6  ω     56.00 112.00   0.50    0.42    --  107.75-125.00-150.00  112
  7  ω     35.00  60.00   0.50    0.42    --  107.75 -61.00-180.00   50
  8  ω    106.00 177.00   0.50    0.42    --  107.75  30.00-150.00  142
  9  ω     95.00 175.00   0.50    0.42    --  107.75  30.00   0.00  160
 10  ω     96.00 178.00   0.50    0.42    --  107.75  21.00  84.00  164
 11  ω    105.00 146.00   0.50    0.42    --  107.75  45.00 150.00   82
 12  ω     44.00  69.00   0.50    0.42    --  107.75 -61.00   0.00   50
 13  ω     39.00  64.00   0.50    0.42    --  107.75 -61.00  60.00   50
 14  ω     46.00  71.00   0.50    0.42    --  107.75 -61.00  90.00   50
 15  ω     37.00  69.00   0.50    0.42    --  107.75 -94.00 120.00   64
 16  ω     36.00  71.00   0.50    0.42    --  107.75 -61.00 150.00   70
 17  ω     36.00 112.00   0.50    0.11    --   47.20  21.00  84.00  152
 18  ω     50.00  95.00   0.50    0.11    --   47.20-125.00 120.00   90
 19  ω     39.00 111.00   0.50    0.42    --  107.75-125.00  30.00  144
 20  ω     36.00  61.00   0.50    0.42    --  107.75-125.00 -60.00   50
 21  ω      1.00  32.00   0.50    0.11    --   47.20 -37.00  60.00   62
 22  ω    -19.00  23.00   0.50    0.11    --  -47.20  21.00  84.00   84
 23  ω    -67.00  24.00   0.50    0.11    --  -47.20  77.00 -60.00  182
 24  ω    -25.00   1.00   0.50    0.11    --  -47.20  37.00-150.00   52
 25  ω    -40.00  26.00   0.50    0.11    --  -47.20  37.00-120.00  132
 26  ω    -68.00 -34.00   0.50    0.42    -- -106.00  61.00-120.00   68
 27  ω    -61.00 -35.00   0.50    0.42    -- -106.00  77.00-120.00   52
 28  ω    -71.00 -45.00   0.50    0.42    -- -106.00 135.00 -45.56   52
 29  ω    -88.00 -37.00   0.50    0.42    -- -106.00 125.00   0.00  102
 30  ω    -63.00 -38.00   0.50    0.42    -- -106.00 139.00  61.92   50
 31  ω    -84.00 -58.00   0.50    0.42    -- -106.00  77.00 150.00   52
 32  ω   -108.00 -83.00   0.50    0.42    -- -106.00 112.00 106.58   50
 33  ω   -108.00 -64.00   0.50    0.42    -- -106.00 112.00 133.44   88
 34  ω   -112.00 -49.00   0.50    0.42    -- -106.00 125.00  30.00  126
 35  ω    -69.00 -40.00   0.50    0.42    -- -106.00  61.00 -60.00   58
 36  ω    -71.00 -41.00   0.50    0.42    -- -106.00  61.00 -30.00   60
 37  ω    -84.00 -35.00   0.50    0.11    --  -47.20 -21.00 -81.00   98
 38  ω   -119.00 -93.00   0.50    0.11    --  -47.20 -21.00 -81.00   52
 39  ω   -125.00 -99.00   0.50    0.42    -- -106.00 -94.00 -30.00   52
 40  ω   -174.00-117.00   0.50    0.42    -- -106.00 -21.00 -81.00  114
 41  ω   -173.00-148.00   0.50    0.42    -- -106.00 -94.00 -30.00   50
 42  ω   -177.00-113.00   0.50    0.42    -- -106.00 -15.00 150.00  128
 43  ω   -119.00 -87.00   0.50    0.42    -- -106.00 135.00 -45.56   64
 44  ω   -108.00 -57.00   0.50    0.42    -- -106.00 115.00-107.64  102
 45  ω   -104.00 -64.00   0.50    0.42    -- -106.00  77.00-120.00   80
 46  ω   -107.00 -38.00   0.50    0.42    -- -106.00 106.00-132.70  138
 47  ω   -118.00 -33.00   0.50    0.42    -- -106.00 134.00 -86.78  170
 48  ω   -122.00 -97.00   0.50    0.42    -- -106.00 139.00  61.92   50
 49  ω   -125.00-100.00   0.50    0.42    -- -106.00 143.00 -13.85   50
 50  ω   -120.00 -94.00   0.50    0.42    -- -106.00 136.00-151.32   52
 51  ω   -103.00 -78.00   0.50    0.11    --  -47.20 -21.00 -81.00   50
 52  ω    -17.00  12.00   0.50    0.11    --   18.00 102.00 164.39   58
 53  ω    -41.00 -15.00   0.50    0.11    --  -42.00 -87.00-135.09   52
 54  ω     17.00  42.00   0.50    0.11    --   46.00  90.00  -0.84   50
 55  ω     17.00  42.00   0.50    0.11    --   46.00  90.00  74.81   50
 56  ω    -60.00 -35.00   0.50    0.11    --  -47.20 -37.00  30.00   50
 57  ω     39.00  75.00   0.50    0.11    --   47.20  37.00 -30.00   72
 58  ω     32.00  58.00   0.50    0.11    --   47.20  57.00   0.00   52
 59  ω     38.00  65.00   0.50    0.11    --   47.20  19.00-180.00   54
 60  ω     27.00  53.00   0.50    0.11    --   50.00  78.00  40.44   52
 61  ω     27.00  53.00   0.50    0.11    --   50.00  77.00  99.26   52
 62  ω     31.00  57.00   0.50    0.11    --   54.00  79.00-165.17   52
 63  ω     30.00  56.00   0.50    0.11    --   54.00  79.00 -49.60   52
 64  ω     81.00 126.00   0.50    0.11    --   54.00  79.00-165.17   90
 65  ω     32.00  58.00   0.50    0.11    --   54.00  78.00-119.11   52
 66  ω     32.00  58.00   0.50    0.11    --   54.00  77.00 113.02   52
 67  ω     87.00 113.00   0.50    0.11    --   54.00  78.00-119.11   52
 68  ω     32.00  58.00   0.50    0.11    --   54.00  78.00 140.07   52
 69  ω     31.00  56.00   0.50    0.11    --   54.00  77.00 -77.15   50
 70  ω     31.00  57.00   0.50    0.11    --   54.00  77.00   6.71   52
 71  ω     35.00  61.00   0.50    0.11    --   54.00  75.00 171.52   52
 72  ω     38.00  64.00   0.50    0.11    --   58.00  74.00-101.93   52
 73  ω    -63.00 -38.00   0.50    0.11    --  -62.00 -79.00 121.71   50
 74  ω   -129.00-103.00   0.50    0.11    --  -62.00 -79.00 121.71   52
 75  ω    -73.00 -48.00   0.50    0.11    --  -66.00 -66.00  92.27   50
 76  ω    -73.00 -48.00   0.50    0.11    --  -66.00 -66.00-107.80   50
 77  ω    -72.00 -47.00   0.50    0.11    --  -66.00 -67.00-120.59   50
 78  ω    -73.00 -48.00   0.50    0.11    --  -66.00 -64.00  69.75   50
 79  ω   -139.00 -96.00   0.50    0.11    --  -66.00 -66.00-107.80   86
 80  ω     43.00  69.00   0.50    0.11    --   66.00  78.00  25.29   52
 81  ω     42.00  68.00   0.50    0.11    --   66.00  80.00 -36.83   52
 82  ω    -71.00 -46.00   0.50    0.11    --  -70.00 -79.00 152.06   50
 83  ω    -77.00 -51.00   0.50    0.11    --  -70.00 -68.00-170.12   52
 84  ω    -79.00 -53.00   0.50    0.11    --  -70.00 -66.00 104.61   52
 85  ω    -74.00 -47.00   0.50    0.11    --  -70.00 -78.00-118.19   54
 86  ω    -79.00 -53.00   0.50    0.11    --  -70.00 -67.00 174.04   52
 87  ω     48.00  73.00   0.50    0.11    --   70.00  76.00  62.89   50
 88  ω     47.00  72.00   0.50    0.11    --   70.00  77.00  91.25   50
 89  ω    117.00 143.00   0.50    0.11    --   70.00  77.00  91.25   52
 90  ω     82.00 108.00   0.50    0.11    --   70.00  76.00 -11.03   52
 91  ω     49.00  75.00   0.50    0.11    --   70.00  76.00 -11.03   52
 92  ω    -84.00 -58.00   0.50    0.11    --  -74.00 -65.00 115.72   52
 93  ω   -133.00-107.00   0.50    0.11    --  -74.00 -74.00-131.83   52
 94  ω    -77.00 -52.00   0.50    0.11    --  -74.00 -74.00-131.83   50
 95  ω    -84.00 -58.00   0.50    0.11    --  -74.00 -64.00-110.14   52
 96  ω    -80.00 -54.00   0.50    0.11    --  -74.00 -75.00  50.12   52
 97  ω     55.00  81.00   0.50    0.11    --   74.00  74.00-144.88   52
 98  ω    -86.00 -60.00   0.50    0.42    --  -78.00 -70.00 175.75   52
 99  ω    -83.00 -57.00   0.50    0.42    --  -78.00 -73.00  12.61   52
100  ω    -87.00 -62.00   0.50    0.42    --  -78.00 -63.00  96.19   50
101  ω    -96.00 -67.00   0.50    0.42    --  -82.00 -63.00-102.05   58
102  ω    -90.00 -65.00   0.50    0.42    --  -82.00 -61.00  63.31   50
103  ω    -92.00 -66.00   0.50    0.42    --  -82.00 -66.00-138.63   52
104  ω    -87.00 -61.00   0.50    0.42    --  -82.00 -74.00 -44.35   52
105  ω    -87.00 -61.00   0.50    0.42    --  -82.00 -72.00 -77.23   52
106  ω    -85.00 -60.00   0.50    0.42    --  -82.00 -74.00  64.63   50
107  ω    -90.00 -64.00   0.50    0.42    --  -82.00 -66.00 157.17   52
108  ω    -90.00 -65.00   0.50    0.42    --  -86.00 -73.00 -23.67   50
109  ω    -90.00 -65.00   0.50    0.42    --  -86.00 -73.00 -10.27   50
110  ω   -101.00 -72.00   0.50    0.42    --  -90.00 -65.00-126.74   58
111  ω   -100.00 -74.00   0.50    0.42    --  -90.00 -63.00  98.25   52
112  ω   -100.00 -74.00   0.50    0.42    --  -90.00 -62.00  89.61   52
113  ω    -98.00 -72.00   0.50    0.42    --  -90.00 -66.00 151.28   52
114  ω    -97.00 -72.00   0.50    0.42    --  -90.00 -66.00 140.20   50
115  ω    -95.00 -69.00   0.50    0.42    --  -90.00 -76.00 -47.88   52
116  ω    -93.00 -68.00   0.50    0.42    --  -90.00 -74.00   9.29   50
117  ω   -150.00-124.00   0.50    0.42    --  -90.00 -74.00   9.29   52
118  ω    -97.00 -71.00   0.50    0.42    --  -90.00 -67.00 162.98   52
119  ω    -96.00 -70.00   0.50    0.42    --  -90.00 -71.00 130.78   52
120  ω   -100.00 -72.00   0.50    0.42    --  -90.00 -64.00-103.25   56
121  ω    -93.00 -68.00   0.50    0.42    --  -90.00 -74.00  51.10   50
122  ω   -105.00 -75.00   0.50    0.42    --  -94.00 -68.00-135.42   60
123  ω   -105.00 -75.00   0.50    0.42    --  -94.00 -68.00-169.28   60
124  ω   -101.00 -76.00   0.50    0.42    --  -94.00 -64.00  88.35   50
125  ω    -97.00 -71.00   0.50    0.42    --  -94.00 -76.00  74.94   52
126  ω   -164.00-138.00   0.50    0.42    --  -94.00 -76.00  74.94   52
127  ω   -102.00 -76.00   0.50    0.42    --  -94.00 -66.00 114.43   52
128  ω   -113.00 -74.00   0.50    0.42    --  -98.00 -79.00 -32.50   78
129  ω   -156.00-130.00   0.50    0.42    --  -98.00 -79.00 -32.50   52
130  ω   -104.00 -79.00   0.50    0.42    --  -98.00 -69.00-124.39   50
131  ω   -101.00 -75.00   0.50    0.42    --  -98.00 -76.00  69.20   52
132  ω   -104.00 -78.00   0.50    0.42    --  -98.00 -69.00-177.89   52
133  ω   -105.00 -79.00   0.50    0.42    -- -102.00 -78.00  41.05   52
134  ω   -158.00-132.00   0.50    0.42    -- -102.00 -78.00  41.05   52
135  ω    -62.00 -36.00   0.50    0.42    -- -106.00  61.00   0.00   52
136  ω   -118.00 -79.00   0.50    0.42    -- -106.00 -85.00  31.95   78
137  ω   -127.00 -88.00   0.50    0.42    -- -106.00 -66.00  51.60   78
138  ω   -167.00-126.00   0.50    0.42    -- -106.00 -85.00  31.95   82
139  ω   -130.00 -83.00   0.50    0.42    -- -106.00 -77.00  30.00   94
140  ω   -174.00-142.00   0.50    0.42    -- -106.00 -66.00  51.60   64
141  ω   -153.00 -86.00   0.50    0.42    -- -106.00 -74.00-140.42  134
142  ω   -118.00 -82.00   0.50    0.42    -- -106.00 -81.00 159.86   72
143  ω   -132.00 -84.00   0.50    0.42    -- -106.00 -77.00 125.43   96
144  ω   -111.00 -83.00   0.50    0.42    -- -106.00 -77.00-120.00   56
145  ω   -119.00 -82.00   0.50    0.42    -- -106.00 -80.00 -44.17   74
146  ω   -170.00-129.00   0.50    0.42    -- -106.00 -80.00 -44.17   82
147  ω   -114.00 -88.00   0.50    0.42    -- -106.00 -65.00-118.12   52
148  ω   -167.00-104.00   0.50    0.42    -- -106.00 -72.00  70.23  126
149  ω   -109.00 -81.00   0.50    0.42    -- -106.00 -81.00-126.75   56
150  ω   -147.00-115.00   0.50    0.42    -- -106.00 -81.00-126.75   64
151  ω   -134.00 -85.00   0.50    0.42    -- -106.00 -73.00 137.87   98
152  ω   -108.00 -83.00   0.50    0.42    -- -106.00 109.00-169.51   50
153  ω   -105.00 -80.00   0.50    0.42    -- -106.00 -83.00-153.62   50
154  ω   -119.00 -82.00   0.50    0.42    -- -106.00 -80.00 -87.29   74
155  ω   -113.00 -81.00   0.50    0.42    -- -106.00 -82.00  11.70   64
156  ω   -165.00-129.00   0.50    0.42    -- -106.00 -80.00 -87.29   72
157  ω   -109.00 -83.00   0.50    0.42    -- -106.00 -78.00  -8.86   52
158  ω   -169.00-116.00   0.50    0.42    -- -106.00 -78.00  -8.86  106
159  ω   -110.00 -84.00   0.50    0.42    -- -106.00 -74.00 163.87   52
160  ω   -112.00 -87.00   0.50    0.42    -- -106.00 -70.00 103.63   50
161  ω   -115.00 -86.00   0.50    0.42    -- -106.00 -70.00 -65.75   58
162  ω   -163.00-135.00   0.50    0.42    -- -106.00 -70.00 103.63   56
163  ω   -113.00 -84.00   0.50    0.42    -- -106.00 -75.00 172.32   58
164  ω   -123.00 -91.00   0.50    0.42    -- -106.00 -61.00-120.00   64
165  ω   -173.00-147.00   0.50    0.42    -- -106.00 -75.00 172.32   52
166  ω   -132.00 -90.00   0.50    0.42    -- -106.00 -66.00-166.44   84
167  ω   -127.00-102.00   0.50    0.42    -- -106.00 -15.00 -90.00   50
168  ω   -175.00-150.00   0.50    0.42    -- -106.00 -15.00 -90.00   50
169  ω   -109.00 -84.00   0.50    0.42    -- -106.00 -74.00  48.73   50
170  ω   -104.00 -79.00   0.50    0.42    -- -106.00 -88.00 117.94   50
171  ω   -164.00-138.00   0.50    0.42    -- -106.00 -66.00-166.44   52
172  ω   -141.00-115.00   0.50    0.42    -- -106.00 -88.00 117.94   52
173  ω    153.00 178.00   0.50    0.42    --  107.75  77.00 -90.00   50
174  ω     85.00 112.00   0.50    0.42    --  107.75  77.00 -90.00   54
175  ω    145.00 175.00   0.50    0.42    --  107.75  77.00  60.00   60
176  ω     85.00 131.00   0.50    0.42    --  107.75  77.00  60.00   92
177  ω    141.00 166.00   0.50    0.42    --  107.75  61.00  90.00   50
178  ω     98.00 124.00   0.50    0.42    --  107.75  61.00  90.00   52
179  ω    140.00 175.00   0.50    0.42    --  107.75  45.00 -60.00   70
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1028027000
_diffrn_orient_matrix_UB_12      0.0400455000
_diffrn_orient_matrix_UB_13      0.1397745000
_diffrn_orient_matrix_UB_21      -0.1529083000
_diffrn_orient_matrix_UB_22      0.0011842000
_diffrn_orient_matrix_UB_23      0.0365397000
_diffrn_orient_matrix_UB_31      -0.0029530000
_diffrn_orient_matrix_UB_32      -0.1348472000
_diffrn_orient_matrix_UB_33      -0.0091176000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0621
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            44689
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.778
_diffrn_reflns_theta_min         4.037
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.665
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85574
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.69a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.455
_exptl_crystal_description       plate
_exptl_crystal_F_000             500
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         4591
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0436
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0450P)²+0.6268P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0942
_refine_ls_wR_factor_ref         0.0959
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4280
_reflns_number_total             4591
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c00611_si_003.cif
_cod_data_source_block           15444_14.11
_cod_depositor_comments
'Adding full bibliography for 4038260--4038261.cif.'
_cod_database_code               4038261
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C27 H19 N3 O4 S '
_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.
;
_diffrn_oxdiff_digest_frames
;
01bbdc61ec36debb5bbf67b598d3b70ba10005008bb
;
_diffrn_oxdiff_digest_hkl
;
0115f997b2e852181a83f5863d0a8d333077d8
;
_reflns_odcompleteness_completeness 99.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C9(H9), C26(H26), C16(H16), C17(H17), C5(H5), C25(H25), C20(H20),
 C23(H23), C27(H27), C6(H6), C21(H21), C22(H22)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C1(H1A,H1B,H1C)
;
_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 1.519
_oxdiff_exptl_absorpt_empirical_full_min 0.391
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
S1 S 0.40254(4) 0.77922(3) -0.02038(3) 0.02012(10) Uani 1 1 d . . . . .
O2 O 0.96523(11) 0.89436(9) 0.16723(10) 0.0211(2) Uani 1 1 d . . . . .
O4 O -0.02602(11) 0.23787(9) 0.18249(9) 0.0211(2) Uani 1 1 d . . . . .
O3 O 0.05201(11) 0.38857(9) 0.37079(9) 0.0213(2) Uani 1 1 d . . . . .
O1 O 1.09305(13) 0.73336(10) 0.14909(12) 0.0293(3) Uani 1 1 d . . . . .
N0AA N 0.29569(14) 0.23612(11) 0.38809(11) 0.0184(2) Uani 1 1 d . . . . .
N1 N 0.55628(14) 0.64272(10) 0.12101(11) 0.0179(2) Uani 1 1 d . . . . .
N2 N 0.48833(14) 0.44403(10) 0.28660(11) 0.0176(2) Uani 1 1 d . . . . .
C13 C 0.06735(16) 0.32551(13) 0.26022(13) 0.0183(3) Uani 1 1 d . . . . .
C4 C 0.67200(16) 0.71091(12) 0.10576(12) 0.0171(3) Uani 1 1 d . . . . .
C11 C 0.20621(16) 0.38676(12) 0.24058(13) 0.0177(3) Uani 1 1 d . . . . .
C12 C 0.36705(16) 0.38527(12) 0.30418(13) 0.0170(3) Uani 1 1 d . . . . .
C8 C 0.45435(16) 0.50589(12) 0.20579(13) 0.0179(3) Uani 1 1 d . . . . .
C15 C 0.41124(16) 0.31698(12) 0.39342(12) 0.0171(3) Uani 1 1 d . . . . .
C7 C 0.59268(16) 0.57422(12) 0.19385(13) 0.0183(3) Uani 1 1 d . . . . .
C3 C 0.83448(16) 0.71046(12) 0.16689(13) 0.0184(3) Uani 1 1 d . . . . .
C10 C 0.17315(16) 0.44802(13) 0.15434(13) 0.0192(3) Uani 1 1 d . . . . .
H10 H 0.0678 0.4478 0.1089 0.023 Uiso 1 1 calc R . . . .
C9 C 0.29826(17) 0.50946(13) 0.13659(13) 0.0198(3) Uani 1 1 d . . . . .
H9 H 0.2788 0.5519 0.0801 0.024 Uiso 1 1 calc R . . . .
C26 C 0.55804(17) 0.87969(12) -0.12578(13) 0.0197(3) Uani 1 1 d . . . . .
H26 H 0.5827 0.9203 -0.1763 0.024 Uiso 1 1 calc R . . . .
C19 C 0.32892(16) 0.17419(13) 0.47129(13) 0.0185(3) Uani 1 1 d . . . . .
C24 C 0.60665(16) 0.77708(12) 0.01912(13) 0.0173(3) Uani 1 1 d . . . . .
C16 C 0.56945(16) 0.33978(13) 0.47883(13) 0.0190(3) Uani 1 1 d . . . . .
H16 H 0.6483 0.3955 0.4777 0.023 Uiso 1 1 calc R . . . .
C17 C 0.60381(17) 0.27851(13) 0.56254(13) 0.0205(3) Uani 1 1 d . . . . .
H17 H 0.7067 0.2923 0.6193 0.025 Uiso 1 1 calc R . . . .
C2 C 0.97706(16) 0.77875(13) 0.15867(13) 0.0194(3) Uani 1 1 d . . . . .
C5 C 0.87010(17) 0.63533(13) 0.23997(14) 0.0219(3) Uani 1 1 d . . . . .
H5 H 0.9763 0.6313 0.2787 0.026 Uiso 1 1 calc R . . . .
C25 C 0.67191(16) 0.83343(12) -0.04637(13) 0.0188(3) Uani 1 1 d . . . . .
H25 H 0.7795 0.8404 -0.0393 0.023 Uiso 1 1 calc R . . . .
C18 C 0.48214(17) 0.19378(13) 0.56277(13) 0.0195(3) Uani 1 1 d . . . . .
C20 C 0.20496(17) 0.08809(14) 0.46634(14) 0.0232(3) Uani 1 1 d . . . . .
H20 H 0.1049 0.0729 0.4054 0.028 Uiso 1 1 calc R . . . .
C23 C 0.50559(18) 0.13107(14) 0.65024(14) 0.0249(3) Uani 1 1 d . . . . .
H23 H 0.6048 0.1450 0.7118 0.030 Uiso 1 1 calc R . . . .
C27 C 0.40827(17) 0.85807(13) -0.11980(13) 0.0207(3) Uani 1 1 d . . . . .
H27 H 0.3196 0.8833 -0.1646 0.025 Uiso 1 1 calc R . . . .
C14 C -0.07223(18) 0.33157(14) 0.40221(15) 0.0256(3) Uani 1 1 d . . . . .
H14A H -0.1735 0.3207 0.3384 0.038 Uiso 1 1 calc GR . . . .
H14B H -0.0761 0.3827 0.4817 0.038 Uiso 1 1 calc GR . . . .
H14C H -0.0495 0.2535 0.4074 0.038 Uiso 1 1 calc GR . . . .
C1 C 1.09433(17) 0.95848(14) 0.14611(15) 0.0238(3) Uani 1 1 d . . . . .
H1A H 1.1016 0.9142 0.0655 0.036 Uiso 1 1 calc GR . . . .
H1B H 1.1933 0.9648 0.2106 0.036 Uiso 1 1 calc GR . . . .
H1C H 1.0734 1.0388 0.1483 0.036 Uiso 1 1 calc GR . . . .
C6 C 0.75015(17) 0.56700(14) 0.25568(14) 0.0225(3) Uani 1 1 d . . . . .
H6 H 0.7734 0.5180 0.3056 0.027 Uiso 1 1 calc R . . . .
C21 C 0.23207(19) 0.02721(15) 0.55102(16) 0.0272(3) Uani 1 1 d . . . . .
H21 H 0.1504 -0.0296 0.5468 0.033 Uiso 1 1 calc R . . . .
C22 C 0.3828(2) 0.05000(15) 0.64465(15) 0.0287(3) Uani 1 1 d . . . . .
H22 H 0.3990 0.0097 0.7030 0.034 Uiso 1 1 calc R . . . .
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_
_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
C27 S1 C24 91.98(7) . . ?
C2 O2 C1 114.63(11) . . ?
C13 O3 C14 114.76(11) . . ?
C15 N0AA C19 118.37(12) . . ?
C7 N1 C4 120.84(12) . . ?
C12 N2 C8 118.62(12) . . ?
O4 C13 O3 124.60(12) . . ?
O4 C13 C11 124.29(12) . . ?
O3 C13 C11 110.80(11) . . ?
N1 C4 C3 120.28(12) . . ?
N1 C4 C24 112.26(12) . . ?
C3 C4 C24 127.44(12) . . ?
C12 C11 C13 123.70(12) . . ?
C10 C11 C13 117.67(12) . . ?
C10 C11 C12 118.63(12) . . ?
N2 C12 C11 121.98(13) . . ?
N2 C12 C15 116.43(12) . . ?
C11 C12 C15 121.59(12) . . ?
N2 C8 C7 116.64(12) . . ?
N2 C8 C9 123.04(12) . . ?
C9 C8 C7 120.31(12) . . ?
N0AA C15 C12 116.19(12) . . ?
N0AA C15 C16 123.20(13) . . ?
C16 C15 C12 120.61(12) . . ?
N1 C7 C8 115.67(12) . . ?
N1 C7 C6 122.43(12) . . ?
C6 C7 C8 121.89(13) . . ?
C4 C3 C2 127.18(12) . . ?
C5 C3 C4 117.97(12) . . ?
C5 C3 C2 114.81(12) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 C11 119.47(13) . . ?
C9 C10 H10 120.3 . . ?
C8 C9 H9 120.9 . . ?
C10 C9 C8 118.21(13) . . ?
C10 C9 H9 120.9 . . ?
C25 C26 H26 123.8 . . ?
C27 C26 H26 123.8 . . ?
C27 C26 C25 112.48(13) . . ?
N0AA C19 C18 122.41(13) . . ?
N0AA C19 C20 118.48(12) . . ?
C20 C19 C18 119.11(13) . . ?
C4 C24 S1 116.16(10) . . ?
C25 C24 S1 110.39(10) . . ?
C25 C24 C4 133.29(13) . . ?
C15 C16 H16 120.6 . . ?
C17 C16 C15 118.85(13) . . ?
C17 C16 H16 120.6 . . ?
C16 C17 H17 120.1 . . ?
C16 C17 C18 119.80(13) . . ?
C18 C17 H17 120.1 . . ?
O2 C2 C3 113.73(12) . . ?
O1 C2 O2 123.82(13) . . ?
O1 C2 C3 122.41(13) . . ?
C3 C5 H5 119.5 . . ?
C6 C5 C3 121.01(13) . . ?
C6 C5 H5 119.5 . . ?
C26 C25 H25 123.5 . . ?
C24 C25 C26 113.00(12) . . ?
C24 C25 H25 123.5 . . ?
C17 C18 C19 117.30(13) . . ?
C23 C18 C19 119.30(13) . . ?
C23 C18 C17 123.39(13) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 C19 120.21(14) . . ?
C21 C20 H20 119.9 . . ?
C18 C23 H23 119.9 . . ?
C22 C23 C18 120.29(14) . . ?
C22 C23 H23 119.9 . . ?
S1 C27 H27 123.9 . . ?
C26 C27 S1 112.12(11) . . ?
C26 C27 H27 123.9 . . ?
O3 C14 H14A 109.5 . . ?
O3 C14 H14B 109.5 . . ?
O3 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O2 C1 H1A 109.5 . . ?
O2 C1 H1B 109.5 . . ?
O2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C7 C6 H6 121.3 . . ?
C5 C6 C7 117.43(13) . . ?
C5 C6 H6 121.3 . . ?
C20 C21 H21 119.7 . . ?
C20 C21 C22 120.56(14) . . ?
C22 C21 H21 119.7 . . ?
C23 C22 C21 120.47(14) . . ?
C23 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
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 C24 1.7358(14) . ?
S1 C27 1.7077(15) . ?
O2 C2 1.3336(18) . ?
O2 C1 1.4519(16) . ?
O4 C13 1.2043(17) . ?
O3 C13 1.3434(17) . ?
O3 C14 1.4473(16) . ?
O1 C2 1.2055(18) . ?
N0AA C15 1.3223(17) . ?
N0AA C19 1.3651(18) . ?
N1 C4 1.3464(17) . ?
N1 C7 1.3304(18) . ?
N2 C12 1.3403(17) . ?
N2 C8 1.3419(18) . ?
C13 C11 1.4972(18) . ?
C4 C3 1.4107(19) . ?
C4 C24 1.4721(19) . ?
C11 C12 1.4075(19) . ?
C11 C10 1.389(2) . ?
C12 C15 1.4856(19) . ?
C8 C7 1.4862(18) . ?
C8 C9 1.3963(19) . ?
C15 C16 1.4200(19) . ?
C7 C6 1.394(2) . ?
C3 C2 1.4957(18) . ?
C3 C5 1.395(2) . ?
C10 H10 0.9300 . ?
C10 C9 1.3852(19) . ?
C9 H9 0.9300 . ?
C26 H26 0.9300 . ?
C26 C25 1.418(2) . ?
C26 C27 1.364(2) . ?
C19 C18 1.4196(19) . ?
C19 C20 1.4173(19) . ?
C24 C25 1.3758(19) . ?
C16 H16 0.9300 . ?
C16 C17 1.365(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.418(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.3791(19) . ?
C25 H25 0.9300 . ?
C18 C23 1.414(2) . ?
C20 H20 0.9300 . ?
C20 C21 1.370(2) . ?
C23 H23 0.9300 . ?
C23 C22 1.369(2) . ?
C27 H27 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C6 H6 0.9300 . ?
C21 H21 0.9300 . ?
C21 C22 1.411(2) . ?
C22 H22 0.9300 . ?
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 C24 C25 C26 1.10(15) . . . . ?
O4 C13 C11 C12 -112.03(17) . . . . ?
O4 C13 C11 C10 67.82(19) . . . . ?
O3 C13 C11 C12 74.12(17) . . . . ?
O3 C13 C11 C10 -106.02(14) . . . . ?
N0AA C15 C16 C17 -2.2(2) . . . . ?
N0AA C19 C18 C17 -2.1(2) . . . . ?
N0AA C19 C18 C23 176.66(13) . . . . ?
N0AA C19 C20 C21 -177.75(14) . . . . ?
N1 C4 C3 C2 178.95(13) . . . . ?
N1 C4 C3 C5 1.6(2) . . . . ?
N1 C4 C24 S1 12.09(15) . . . . ?
N1 C4 C24 C25 -162.89(14) . . . . ?
N1 C7 C6 C5 0.6(2) . . . . ?
N2 C12 C15 N0AA -164.06(12) . . . . ?
N2 C12 C15 C16 16.22(18) . . . . ?
N2 C8 C7 N1 -174.83(12) . . . . ?
N2 C8 C7 C6 4.91(19) . . . . ?
N2 C8 C9 C10 1.3(2) . . . . ?
C13 C11 C12 N2 -178.14(12) . . . . ?
C13 C11 C12 C15 2.6(2) . . . . ?
C13 C11 C10 C9 177.78(12) . . . . ?
C4 N1 C7 C8 178.38(11) . . . . ?
C4 N1 C7 C6 -1.4(2) . . . . ?
C4 C3 C2 O2 44.39(19) . . . . ?
C4 C3 C2 O1 -137.76(16) . . . . ?
C4 C3 C5 C6 -2.3(2) . . . . ?
C4 C24 C25 C26 176.29(14) . . . . ?
C11 C12 C15 N0AA 15.23(19) . . . . ?
C11 C12 C15 C16 -164.50(13) . . . . ?
C11 C10 C9 C8 0.8(2) . . . . ?
C12 N2 C8 C7 177.28(11) . . . . ?
C12 N2 C8 C9 -1.7(2) . . . . ?
C12 C11 C10 C9 -2.4(2) . . . . ?
C12 C15 C16 C17 177.55(12) . . . . ?
C8 N2 C12 C11 -0.01(19) . . . . ?
C8 N2 C12 C15 179.27(11) . . . . ?
C8 C7 C6 C5 -179.08(13) . . . . ?
C15 N0AA C19 C18 0.1(2) . . . . ?
C15 N0AA C19 C20 179.56(12) . . . . ?
C15 C16 C17 C18 0.1(2) . . . . ?
C7 N1 C4 C3 0.17(19) . . . . ?
C7 N1 C4 C24 178.47(12) . . . . ?
C7 C8 C9 C10 -177.65(12) . . . . ?
C3 C4 C24 S1 -169.76(11) . . . . ?
C3 C4 C24 C25 15.3(2) . . . . ?
C3 C5 C6 C7 1.2(2) . . . . ?
C10 C11 C12 N2 2.0(2) . . . . ?
C10 C11 C12 C15 -177.24(12) . . . . ?
C9 C8 C7 N1 4.14(19) . . . . ?
C9 C8 C7 C6 -176.13(13) . . . . ?
C19 N0AA C15 C12 -177.68(11) . . . . ?
C19 N0AA C15 C16 2.0(2) . . . . ?
C19 C18 C23 C22 1.7(2) . . . . ?
C19 C20 C21 C22 0.5(2) . . . . ?
C24 S1 C27 C26 1.47(12) . . . . ?
C24 C4 C3 C2 0.9(2) . . . . ?
C24 C4 C3 C5 -176.38(13) . . . . ?
C16 C17 C18 C19 1.9(2) . . . . ?
C16 C17 C18 C23 -176.77(13) . . . . ?
C17 C18 C23 C22 -179.71(14) . . . . ?
C2 C3 C5 C6 -179.97(13) . . . . ?
C5 C3 C2 O2 -138.22(13) . . . . ?
C5 C3 C2 O1 39.6(2) . . . . ?
C25 C26 C27 S1 -1.10(16) . . . . ?
C18 C19 C20 C21 1.7(2) . . . . ?
C18 C23 C22 C21 0.6(2) . . . . ?
C20 C19 C18 C17 178.50(13) . . . . ?
C20 C19 C18 C23 -2.8(2) . . . . ?
C20 C21 C22 C23 -1.7(2) . . . . ?
C27 S1 C24 C4 -177.56(11) . . . . ?
C27 S1 C24 C25 -1.45(11) . . . . ?
C27 C26 C25 C24 -0.02(18) . . . . ?
C14 O3 C13 O4 10.4(2) . . . . ?
C14 O3 C13 C11 -175.74(11) . . . . ?
C1 O2 C2 O1 8.4(2) . . . . ?
C1 O2 C2 C3 -173.75(11) . . . . ?
