#------------------------------------------------------------------------------
#$Date: 2020-10-04 06:35:42 +0300 (Sun, 04 Oct 2020) $
#$Revision: 257131 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/88/4038817.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_4038817
loop_
_publ_author_name
'Pozharskii, Alexander F.'
'Dyablo, Olga V.'
'Pogosova, Olga G.'
'Ozeryanskii, Valery A.'
'Filarowski, Aleksander'
'Vasilikhina, Kseniya M.'
'Dzhangiryan, Narek A.'
_publ_section_title
;
 Modeling Biologically Important NH···π Interactions
 Using peri-Disubstituted Naphthalenes.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12468
_journal_page_last               12481
_journal_paper_doi               10.1021/acs.joc.0c01697
_journal_volume                  85
_journal_year                    2020
_chemical_formula_moiety         'C22 H20 N, B F4'
_chemical_formula_sum            'C22 H20 B F4 N'
_chemical_formula_weight         385.20
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2020-04-18
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                90
_cell_angle_beta                 96.044(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.0267(4)
_cell_length_b                   8.0762(3)
_cell_length_c                   19.1306(5)
_cell_measurement_reflns_used    9109
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      69.3900
_cell_measurement_theta_min      4.1390
_cell_volume                     1847.83(10)
_computing_cell_refinement       'CrysAlisPro 1.171.40.50a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.50a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.50a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω   -107.00 -76.00   0.50    2.16    --  -38.95 -27.00 -45.00   62
  2  ω    -49.00 -23.00   0.50    2.16    --  -38.95 -27.00 -45.00   52
  3  ω    -31.00   5.00   0.50    2.16    --   38.95 -27.00 -45.00   72
  4  ω     29.00 100.00   0.50    2.16    --   38.95  27.00 117.00  142
  5  ω     30.00 113.00   0.50    8.64    --  100.00 -27.00 -45.00  166
  6  ω     97.00 142.00   0.50    8.64    --  100.00  27.00 117.00   90
  7  ω    -43.00  27.00   0.50    2.16    --  -38.95  43.00-150.00  140
  8  ω    -57.00 -17.00   0.50    2.16    --  -38.95  54.00 -90.00   80
  9  ω   -104.00 -76.00   0.50    2.16    --  -38.95 -32.00 -60.00   56
 10  ω     -5.00  21.00   0.50    2.16    --  -38.95  27.00 117.00   52
 11  ω    -70.00 -36.00   0.50    2.16    --  -38.95 -32.00 -60.00   68
 12  ω    -42.00 -16.00   0.50    2.16    --  -38.95  27.00 117.00   52
 13  ω     -9.00  17.00   0.50    2.16    --  -38.95  54.00 -90.00   52
 14  ω     28.00  53.00   0.50    2.16    --   38.95  54.00 -90.00   50
 15  ω    -10.00  22.00   0.50    2.16    --   38.95-104.00 -90.00   64
 16  ω    -29.00  30.00   0.50    2.16    --   38.95 -32.00   0.00  118
 17  ω     33.00  58.00   0.50    2.16    --   38.95 -65.00-150.00   50
 18  ω     44.00  69.00   0.50    2.16    --   38.95-104.00 -90.00   50
 19  ω     70.00  97.00   0.50    2.16    --   38.95  54.00 -90.00   54
 20  ω    -13.00  12.00   0.50    2.16    --   38.95 -65.00-150.00   50
 21  ω     32.00  74.00   0.50    8.64    --  100.00-111.00 120.00   84
 22  ω    109.00 151.00   0.50    8.64    --  100.00  37.00 150.00   84
 23  ω    109.00 155.00   0.50    8.64    --  100.00  30.00   0.00   92
 24  ω     40.00 118.00   0.50    8.64    --  100.00 -61.00   0.00  156
 25  ω     34.00 124.00   0.50    8.64    --  100.00 -69.00 120.00  180
 26  ω    127.00 156.00   0.50    8.64    --  100.00  61.00 -60.00   58
 27  ω     35.00 109.00   0.50    8.64    --  100.00 -45.00 120.00  148
 28  ω     78.00 113.00   0.50    8.64    --  100.00  61.00 -60.00   70
 29  ω     77.00 102.00   0.50    8.64    --  100.00 -93.00  60.00   50
 30  ω     83.00 118.00   0.50    8.64    --  100.00 -22.00  90.00   70
 31  ω     72.00 105.00   0.50    8.64    --  100.00 133.00 120.00   66
 32  ω    108.00 157.00   0.50    8.64    --  100.00  53.00 120.00   98
 33  ω     89.00 114.00   0.50    8.64    --  100.00  77.00-150.00   50
 34  ω     81.00 107.00   0.50    8.64    --  100.00-111.00 120.00   52
 35  ω     81.00 123.00   0.50    8.64    --  100.00  93.00-120.00   84
 36  ω     97.00 123.00   0.50    8.64    --  100.00  45.00-120.00   52
 37  ω    130.00 155.00   0.50    8.64    --  100.00  30.00 -90.00   50
 38  ω     75.00 101.00   0.50    8.64    --  100.00 -61.00 120.00   52
 39  ω     90.00 115.00   0.50    8.64    --  100.00 -37.00   0.00   50
 40  ω    114.00 139.00   0.50    8.64    --  100.00  53.00-180.00   50
 41  ω     86.00 112.00   0.50    8.64    --  100.00  53.00-180.00   52
 42  ω     49.00  77.00   0.50    8.64    --  100.00 -37.00   0.00   56
 43  ω     45.00 108.00   0.50    8.64    --  100.00 -93.00 120.00  126
 44  ω     40.00  65.00   0.50    8.64    --  100.00 -22.00  90.00   50
 45  ω     16.00  52.00   0.50    2.16    --   38.95  77.00-180.00   72
 46  ω    -40.00 -14.00   0.50    2.16    --  -38.95 -77.00-180.00   52
 47  ω    -82.00 -56.00   0.50    2.16    --  -38.95 -77.00-180.00   52
 48  ω    -99.00 -57.00   0.50    2.16    --  -38.95 -54.00-120.00   84
 49  ω    -49.00 -19.00   0.50    2.16    --  -38.95 -54.00-120.00   60
 50  ω     21.00  46.00   0.50    2.16    --   38.95  77.00-150.00   50
 51  ω     66.00  92.00   0.50    2.16    --   38.95  65.00-120.00   52
 52  ω     13.00  39.00   0.50    2.16    --   38.95  77.00-120.00   52
 53  ω     71.00  96.00   0.50    2.16    --   38.95  77.00-180.00   50
 54  ω     17.00  43.00   0.50    2.16    --   38.95  65.00-120.00   52
 55  ω     18.00  48.00   0.50    2.16    --   38.95 -65.00  90.00   60
 56  ω     17.00  43.00   0.50    2.16    --   38.95  65.00 -60.00   52
 57  ω     47.00  73.00   0.50    2.16    --   38.95  77.00-150.00   52
 58  ω     29.00  54.00   0.50    2.16    --   38.95  54.00-120.00   50
 59  ω     -6.00  30.00   0.50    2.16    --   38.95 -32.00 -30.00   72
 60  ω     23.00  48.00   0.50    2.16    --   38.95  54.00-150.00   50
 61  ω    121.00 148.00   0.50    8.64    --  100.00  69.00-180.00   54
 62  ω     76.00 102.00   0.50    8.64    --  100.00  69.00-180.00   52
 63  ω    114.00 144.00   0.50    8.64    --  100.00  77.00 -90.00   60
 64  ω    123.00 149.00   0.50    8.64    --  100.00  77.00-150.00   52
 65  ω     74.00 100.00   0.50    8.64    --  100.00  77.00-150.00   52
 66  ω     73.00  98.00   0.50    8.64    --  100.00  77.00 -90.00   50
 67  ω    117.00 143.00   0.50    8.64    --  100.00  66.00-160.57   52
 68  ω     39.00  72.00   0.50    8.64    --  100.00 -22.00  60.00   66
 69  ω     94.00 119.00   0.50    8.64    --  100.00 -22.00  60.00   50
 70  ω     78.00 135.00   0.50    8.64    --  100.00  61.00-120.00  114
 71  ω     73.00  99.00   0.50    8.64    --  100.00  77.00-120.00   52
 72  ω     77.00 102.00   0.50    8.64    --  100.00  68.00 165.25   50
 73  ω    130.00 155.00   0.50    8.64    --  100.00  68.00 165.25   50
 74  ω     73.00 103.00   0.50    8.64    --  100.00  77.00-180.00   60
 75  ω     78.00 103.00   0.50    8.64    --  100.00  61.00 150.00   50
 76  ω     79.00 119.00   0.50    8.64    --  100.00  57.00 158.51   80
 77  ω     68.00  94.00   0.50    8.64    --  100.00 -53.00-120.00   52
 78  ω    108.00 134.00   0.50    8.64    --  100.00  77.00 120.00   52
 79  ω     79.00 105.00   0.50    8.64    --  100.00  77.00 120.00   52
 80  ω     76.00 102.00   0.50    8.64    --  100.00  69.00 -90.00   52
 81  ω     79.00 105.00   0.50    8.64    --  100.00  61.00-180.00   52
 82  ω    112.00 157.00   0.50    8.64    --  100.00  69.00-120.00   90
 83  ω    108.00 154.00   0.50    8.64    --  100.00  61.00-150.00   92
 84  ω     78.00 104.00   0.50    8.64    --  100.00  61.00-150.00   52
 85  ω     80.00 130.00   0.50    8.64    --  100.00  53.00 -90.00  100
 86  ω     38.00  78.00   0.50    8.64    --  100.00 -22.00 150.00   80
 87  ω     83.00 108.00   0.50    8.64    --  100.00 -93.00   0.00   50
 88  ω    132.00 157.00   0.50    8.64    --  100.00  77.00 150.00   50
 89  ω     30.00  62.00   0.50    8.64    --  100.00 -93.00   0.00   64
 90  ω     78.00 104.00   0.50    8.64    --  100.00  61.00 -90.00   52
 91  ω     76.00 106.00   0.50    8.64    --  100.00  69.00-150.00   60
 92  ω    119.00 144.00   0.50    8.64    --  100.00  61.00 150.00   50
 93  ω    105.00 136.00   0.50    8.64    --  100.00 133.00 -60.00   62
 94  ω     73.00  98.00   0.50    8.64    --  100.00  77.00 150.00   50
 95  ω     87.00 112.00   0.50    8.64    --  100.00  30.00 120.00   50
 96  ω     86.00 111.00   0.50    8.64    --  100.00  45.00 -90.00   50
 97  ω     80.00 106.00   0.50    8.64    --  100.00  53.00-120.00   52
 98  ω     34.00  60.00   0.50    8.64    --  100.00 -93.00 -90.00   52
 99  ω     76.00 101.00   0.50    8.64    --  100.00  69.00-120.00   50
100  ω     77.00 111.00   0.50    8.64    --  100.00  66.00-160.57   68
101  ω     49.00  75.00   0.50    2.16    --   38.95-119.00-115.00   52
102  ω    -61.00 -26.00   0.50    2.16    --  -38.95  65.00  30.00   70
103  ω    -66.00 -40.00   0.50    2.16    --  -38.95  77.00  90.00   52
104  ω    -35.00  10.00   0.50    2.16    --  -38.95  77.00  90.00   90
105  ω      2.00  28.00   0.50    2.16    --   38.95 -65.00 -60.00   52
106  ω     46.00  85.00   0.50    2.16    --   38.95-138.00 120.00   78
107  ω     93.00 122.00   0.50    8.64    --  100.00-133.00 -30.00   58
108  ω     68.00 125.00   0.50    8.64    --  100.00 -77.00 -60.00  114
109  ω     65.00 110.00   0.50    8.64    --  100.00 -53.00 -90.00   90
110  ω     83.00 123.00   0.50    8.64    --  100.00-133.00 120.00   80
111  ω     75.00 101.00   0.50    8.64    --  100.00 -69.00-150.00   52
112  ω    108.00 134.00   0.50    8.64    --  100.00  30.00 -30.00   52
113  ω     41.00  67.00   0.50    8.64    --  100.00 -93.00 150.00   52
114  ω     82.00 108.00   0.50    8.64    --  100.00 -93.00 150.00   52
115  ω     95.00 122.00   0.50    8.64    --  100.00-133.00  60.00   54
116  ω     77.00 102.00   0.50    8.64    --  100.00 -30.00-120.00   50
117  ω     47.00  73.00   0.50    8.64    --  100.00 -69.00-150.00   52
118  ω     50.00  95.00   0.50    8.64    --  100.00 -61.00  90.00   90
119  ω     55.00 109.00   0.50    8.64    --  100.00-111.00 -60.00  108
120  ω     56.00  81.00   0.50    8.64    --  100.00-111.00 -90.00   50
121  ω    103.00 129.00   0.50    8.64    --  100.00  30.00 -60.00   52
122  ω     82.00 107.00   0.50    8.64    --  100.00  93.00 -30.00   50
123  ω    132.00 157.00   0.50    8.64    --  100.00  93.00  30.00   50
124  ω     35.00  85.00   0.50    8.64    --  100.00 -37.00-120.00  100
125  ω     66.00  92.00   0.50    8.64    --  100.00 -53.00  30.00   52
126  ω     32.00  93.00   0.50    8.64    --  100.00 -93.00 -60.00  122
127  ω     43.00  69.00   0.50    2.16    --   38.95-119.00-115.00   52
128  ω    -35.00 -10.00   0.50    2.16    --    8.00 113.00 -32.47   50
129  ω    -20.00   5.00   0.50    2.16    --   24.00 115.00 179.35   50
130  ω    -13.00  12.00   0.50    2.16    --   24.00 102.00   6.65   50
131  ω     -4.00  22.00   0.50    2.16    --   28.00  97.00  91.68   52
132  ω      1.00  26.00   0.50    2.16    --   32.00  89.00 -88.43   50
133  ω     -1.00  24.00   0.50    2.16    --   32.00  94.00 -61.71   50
134  ω     -1.00  24.00   0.50    2.16    --   32.00  92.00  40.84   50
135  ω      6.00  33.00   0.50    2.16    --   36.00  87.00  98.99   54
136  ω      5.00  30.00   0.50    2.16    --   36.00  89.00-172.32   50
137  ω      6.00  31.00   0.50    2.16    --   36.00  87.00 -30.69   50
138  ω    -60.00  -8.00   0.50    2.16    --  -38.95  65.00 -30.00  104
139  ω     11.00  36.00   0.50    2.16    --   40.00  83.00  -8.52   50
140  ω     16.00  41.00   0.50    2.16    --   44.00  82.00   8.81   50
141  ω     16.00  41.00   0.50    2.16    --   44.00  82.00-125.70   50
142  ω     16.00  41.00   0.50    2.16    --   44.00  80.00  98.80   50
143  ω     16.00  41.00   0.50    2.16    --   44.00  80.00 -50.29   50
144  ω     16.00  41.00   0.50    2.16    --   44.00  80.00 155.15   50
145  ω     16.00  43.00   0.50    2.16    --   44.00  80.00  39.48   54
146  ω     90.00 115.00   0.50    2.16    --   48.00  77.00 -98.31   50
147  ω     21.00  46.00   0.50    2.16    --   48.00  77.00 -98.31   50
148  ω     25.00  53.00   0.50    2.16    --   52.00  77.00-143.75   56
149  ω     27.00  53.00   0.50    2.16    --   52.00  76.00 101.33   52
150  ω     27.00  53.00   0.50    2.16    --   52.00  77.00 -17.26   52
151  ω     28.00  53.00   0.50    2.16    --   52.00  75.00 157.57   50
152  ω     84.00 110.00   0.50    2.16    --   52.00  77.00 -17.26   52
153  ω     27.00  53.00   0.50    2.16    --   52.00  75.00  72.65   52
154  ω     32.00  58.00   0.50    2.16    --   56.00  69.00   0.69   52
155  ω     29.00  55.00   0.50    2.16    --   56.00  77.00 -77.26   52
156  ω     34.00  92.00   0.50    2.16    --   60.00  76.00  34.08  116
157  ω     35.00  66.00   0.50    2.16    --   60.00  73.00 159.79   62
158  ω     46.00  71.00   0.50    2.16    --   64.00  50.00  85.84   50
159  ω     42.00  68.00   0.50    2.16    --   68.00  77.00 109.51   52
160  ω     45.00  71.00   0.50    2.16    --   68.00  69.00-118.37   52
161  ω     94.00 123.00   0.50    2.16    --   68.00  64.00  95.08   58
162  ω     45.00  70.00   0.50    2.16    --   68.00  64.00  95.08   50
163  ω     42.00  68.00   0.50    2.16    --   68.00  76.00 -60.75   52
164  ω     45.00  70.00   0.50    8.64    --   72.00  77.00 179.76   50
165  ω     48.00  73.00   0.50    8.64    --   72.00  67.00  12.99   50
166  ω     49.00  75.00   0.50    8.64    --   72.00  71.00 155.36   52
167  ω     53.00  79.00   0.50    8.64    --   76.00  63.00 -22.34   52
168  ω     54.00  80.00   0.50    8.64    --   76.00  62.00-102.47   52
169  ω     49.00  86.00   0.50    8.64    --   76.00  77.00 -88.86   74
170  ω     56.00  98.00   0.50    8.64    --   80.00  69.00 113.32   84
171  ω     54.00  99.00   0.50    8.64    --   80.00  75.00 122.96   90
172  ω     63.00  89.00   0.50    8.64    --   80.00  65.00-151.41   52
173  ω     54.00  80.00   0.50    8.64    --   80.00  76.00 -65.37   52
174  ω     60.00  86.00   0.50    8.64    --   84.00  71.00-167.32   52
175  ω     59.00  85.00   0.50    8.64    --   84.00  76.00-108.72   52
176  ω     62.00  87.00   0.50    8.64    --   88.00  74.00 -26.93   50
177  ω     69.00  95.00   0.50    8.64    --   96.00  77.00-136.71   52
178  ω     55.00 107.00   0.50    8.64    --  100.00 -45.00  90.00  104
179  ω     76.00 102.00   0.50    8.64    --  100.00  69.00   0.00   52
180  ω     76.00 101.00   0.50    8.64    --  100.00  69.00  90.00   50
181  ω    108.00 144.00   0.50    8.64    --  100.00  77.00 -30.00   72
182  ω    132.00 157.00   0.50    8.64    --  100.00  77.00  60.00   50
183  ω     73.00 107.00   0.50    8.64    --  100.00  77.00 120.00   68
184  ω     75.00 130.00   0.50    8.64    --  100.00  77.00  30.00  110
185  ω     72.00  98.00   0.50    8.64    --  100.00 -45.00 -90.00   52
186  ω     73.00 101.00   0.50    8.64    --  100.00  77.00 -30.00   56
187  ω     78.00 156.00   0.50    8.64    --  100.00  61.00  60.00  156
188  ω     73.00 104.00   0.50    8.64    --  100.00  77.00  60.00   62
189  ω     29.00  93.00   0.50    8.64    --  100.00 -15.00  30.00  128
190  ω     73.00 141.00   0.50    8.64    --  100.00  77.00   0.00  136
191  ω     73.00 133.00   0.50    8.64    --  100.00  77.00 -60.00  120
192  ω     78.00 104.00   0.50    8.64    --  100.00  61.00 120.00   52
193  ω     77.00 142.00   0.50    8.64    --  100.00  69.00  30.00  130
194  ω     74.00 116.00   0.50    8.64    --  100.00  77.00  90.00   84
195  ω     63.00  89.00   0.50    8.64    --  100.00 -15.00-180.00   52
196  ω     25.00  56.00   0.50    8.64    --  100.00 -15.00-180.00   62
197  ω     85.00 134.00   0.50    8.64    --  100.00  93.00 -60.00   98
198  ω     78.00 104.00   0.50    8.64    --  100.00  61.00  30.00   52
199  ω     53.00  91.00   0.50    8.64    --  100.00 -37.00-180.00   76
200  ω     26.00  96.00   0.50    8.64    --  100.00 -15.00-120.00  140
201  ω    105.00 131.00   0.50    8.64    --  100.00  69.00   0.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0501
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            40158
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.902
_diffrn_reflns_theta_min         4.154
_exptl_absorpt_coefficient_mu    0.909
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74046
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.50a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_description       plate
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.811
_refine_diff_density_min         -0.435
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     287
_refine_ls_number_reflns         3539
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0891
_refine_ls_R_factor_gt           0.0821
_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)+(0.0770P)²+3.4071P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2002
_refine_ls_wR_factor_ref         0.2050
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3155
_reflns_number_total             3539
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c01697_si_001.cif
_cod_data_source_block           Struct-4
_cod_depositor_comments
'Adding full bibliography for 4038815--4038822.cif.'
_cod_database_code               4038817
_shelx_shelxl_version_number     2014/7
_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   0.956
_shelx_estimated_absorpt_t_min   0.825
_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. Others
 Sof(F1)=Sof(F3)=Sof(F4)=1-FVAR(1)
 Sof(F26)=Sof(F28)=Sof(F27)=FVAR(1)
3.a Aromatic/amide H refined with riding coordinates:
 C12(H12), C20(H20), C2(H2), C13(H13), C8(H8), C6(H6), C4(H4), C3(H3),
 C18(H18), C15(H15), C7(H7), C16(H16), C17(H17)
3.b Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C22(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
;
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'
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
N21 N 0.2208(2) 0.7171(3) 0.56245(13) 0.0320(6) Uani 1 1 d . . . . .
F24 F 0.1566(2) 0.2495(4) 0.46416(13) 0.0792(8) Uani 1 1 d . . . . .
F26 F 0.0710(15) 0.0234(17) 0.4039(11) 0.124(7) Uani 0.351(16) 1 d . . P A 1
C10 C 0.4152(2) 0.6086(3) 0.59955(14) 0.0289(6) Uani 1 1 d . . . . .
C1 C 0.3848(2) 0.5151(3) 0.65841(14) 0.0287(6) Uani 1 1 d . . . . .
C11 C 0.2678(2) 0.4720(4) 0.67018(14) 0.0297(6) Uani 1 1 d . . . . .
C9 C 0.3403(2) 0.6990(4) 0.55048(14) 0.0310(6) Uani 1 1 d . . . . .
C5 C 0.5310(2) 0.6168(4) 0.58881(16) 0.0365(7) Uani 1 1 d . . . . .
C12 C 0.2090(2) 0.3554(4) 0.62296(16) 0.0359(7) Uani 1 1 d . . . . .
H12 H 0.2443 0.3141 0.5844 0.043 Uiso 1 1 calc R . . . .
C20 C 0.2164(3) 0.5307(4) 0.72564(15) 0.0360(7) Uani 1 1 d . . . . .
H20 H 0.2542 0.6081 0.7571 0.043 Uiso 1 1 calc R . . . .
C19 C 0.1049(3) 0.4757(4) 0.73681(15) 0.0362(7) Uani 1 1 d . . . . .
C14 C 0.0509(3) 0.3614(4) 0.68867(15) 0.0353(7) Uani 1 1 d . . . . .
C2 C 0.4680(3) 0.4482(4) 0.70505(17) 0.0387(7) Uani 1 1 d . . . . .
H2 H 0.4478 0.3926 0.7456 0.046 Uiso 1 1 calc R . . . .
C13 C 0.1036(3) 0.3025(4) 0.63216(16) 0.0372(7) Uani 1 1 d . . . . .
H13 H 0.0663 0.2258 0.6001 0.045 Uiso 1 1 calc R . . . .
C8 C 0.3756(3) 0.7844(4) 0.49538(16) 0.0425(8) Uani 1 1 d . . . . .
H8 H 0.3234 0.8433 0.4640 0.051 Uiso 1 1 calc R . . . .
F28 F 0.0421(18) 0.265(3) 0.3821(16) 0.184(11) Uani 0.351(16) 1 d . . P A 1
C6 C 0.5646(3) 0.7064(4) 0.53101(19) 0.0467(9) Uani 1 1 d . . . . .
H6 H 0.6417 0.7113 0.5244 0.056 Uiso 1 1 calc R . . . .
C23 C 0.1397(3) 0.6693(4) 0.50096(17) 0.0450(8) Uani 1 1 d . . . . .
H23A H 0.1461 0.7468 0.4622 0.067 Uiso 1 1 calc GR . . . .
H23B H 0.0635 0.6729 0.5146 0.067 Uiso 1 1 calc GR . . . .
H23C H 0.1565 0.5569 0.4858 0.067 Uiso 1 1 calc GR . . . .
C4 C 0.6117(3) 0.5395(4) 0.6371(2) 0.0463(9) Uani 1 1 d . . . . .
H4 H 0.6883 0.5436 0.6292 0.056 Uiso 1 1 calc R . . . .
C3 C 0.5814(3) 0.4597(5) 0.6946(2) 0.0474(8) Uani 1 1 d . . . . .
H3 H 0.6368 0.4118 0.7275 0.057 Uiso 1 1 calc R . . . .
C18 C 0.0525(3) 0.5348(5) 0.79409(17) 0.0439(8) Uani 1 1 d . . . . .
H18 H 0.0901 0.6109 0.8263 0.053 Uiso 1 1 calc R . . . .
C15 C -0.0597(3) 0.3075(5) 0.70062(18) 0.0449(8) Uani 1 1 d . . . . .
H15 H -0.0982 0.2301 0.6695 0.054 Uiso 1 1 calc R . . . .
C7 C 0.4898(3) 0.7850(5) 0.48525(18) 0.0507(9) Uani 1 1 d . . . . .
H7 H 0.5142 0.8410 0.4460 0.061 Uiso 1 1 calc R . . . .
C16 C -0.1091(3) 0.3662(5) 0.75578(19) 0.0517(10) Uani 1 1 d . . . . .
H16 H -0.1821 0.3297 0.7630 0.062 Uiso 1 1 calc R . . . .
C22 C 0.1972(3) 0.8890(4) 0.5871(2) 0.0498(9) Uani 1 1 d . . . . .
H22A H 0.2510 0.9176 0.6274 0.075 Uiso 1 1 calc GR . . . .
H22B H 0.1212 0.8936 0.6011 0.075 Uiso 1 1 calc GR . . . .
H22C H 0.2040 0.9679 0.5489 0.075 Uiso 1 1 calc GR . . . .
C17 C -0.0531(3) 0.4821(5) 0.80321(19) 0.0519(9) Uani 1 1 d . . . . .
H17 H -0.0893 0.5232 0.8415 0.062 Uiso 1 1 calc R . . . .
F27 F 0.1939(10) 0.1847(18) 0.3595(4) 0.064(4) Uani 0.351(16) 1 d . . P A 1
B25 B 0.1246(3) 0.1555(5) 0.4069(2) 0.0423(9) Uani 1 1 d . . . . .
F1 F 0.2203(5) 0.0822(17) 0.3837(7) 0.124(4) Uani 0.649(16) 1 d . . P A 2
F3 F 0.0698(5) 0.0173(8) 0.4321(4) 0.075(2) Uani 0.649(16) 1 d . . P A 2
F4 F 0.0507(8) 0.2278(10) 0.3608(3) 0.111(4) Uani 0.649(16) 1 d . . P A 2
H21 H 0.207(3) 0.652(4) 0.5982(19) 0.039(9) Uiso 1 1 d . . . . .
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'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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'
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
C9 N21 C23 114.5(2) . . ?
C9 N21 C22 110.9(2) . . ?
C9 N21 H21 108(2) . . ?
C23 N21 C22 110.8(2) . . ?
C23 N21 H21 107(2) . . ?
C22 N21 H21 104(2) . . ?
C9 C10 C1 126.1(3) . . ?
C5 C10 C1 118.0(3) . . ?
C5 C10 C9 115.9(3) . . ?
C10 C1 C11 124.4(2) . . ?
C2 C1 C10 119.1(3) . . ?
C2 C1 C11 116.3(3) . . ?
C12 C11 C1 117.9(3) . . ?
C20 C11 C1 123.2(3) . . ?
C20 C11 C12 118.8(3) . . ?
C10 C9 N21 120.1(2) . . ?
C8 C9 N21 117.1(3) . . ?
C8 C9 C10 122.6(3) . . ?
C6 C5 C10 119.9(3) . . ?
C4 C5 C10 119.9(3) . . ?
C4 C5 C6 120.2(3) . . ?
C11 C12 H12 119.2 . . ?
C13 C12 C11 121.7(3) . . ?
C13 C12 H12 119.2 . . ?
C11 C20 H20 119.7 . . ?
C11 C20 C19 120.6(3) . . ?
C19 C20 H20 119.7 . . ?
C14 C19 C20 118.2(3) . . ?
C18 C19 C20 120.6(3) . . ?
C18 C19 C14 121.2(3) . . ?
C19 C14 C15 117.6(3) . . ?
C13 C14 C19 120.9(3) . . ?
C13 C14 C15 121.5(3) . . ?
C1 C2 H2 118.9 . . ?
C1 C2 C3 122.1(3) . . ?
C3 C2 H2 118.9 . . ?
C12 C13 C14 119.8(3) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C9 C8 H8 120.1 . . ?
C9 C8 C7 119.8(3) . . ?
C7 C8 H8 120.1 . . ?
C5 C6 H6 119.2 . . ?
C7 C6 C5 121.5(3) . . ?
C7 C6 H6 119.2 . . ?
N21 C23 H23A 109.5 . . ?
N21 C23 H23B 109.5 . . ?
N21 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C5 C4 H4 119.5 . . ?
C3 C4 C5 121.0(3) . . ?
C3 C4 H4 119.5 . . ?
C2 C3 H3 120.2 . . ?
C4 C3 C2 119.7(3) . . ?
C4 C3 H3 120.2 . . ?
C19 C18 H18 120.2 . . ?
C17 C18 C19 119.5(3) . . ?
C17 C18 H18 120.2 . . ?
C14 C15 H15 119.8 . . ?
C16 C15 C14 120.5(3) . . ?
C16 C15 H15 119.8 . . ?
C8 C7 H7 119.9 . . ?
C6 C7 C8 120.3(3) . . ?
C6 C7 H7 119.9 . . ?
C15 C16 H16 119.6 . . ?
C15 C16 C17 120.8(3) . . ?
C17 C16 H16 119.6 . . ?
N21 C22 H22A 109.5 . . ?
N21 C22 H22B 109.5 . . ?
N21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C18 C17 C16 120.5(3) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
F24 B25 F28 92.9(14) . . ?
F24 B25 F1 108.6(4) . . ?
F24 B25 F3 105.8(5) . . ?
F26 B25 F24 128.3(10) . . ?
F26 B25 F28 100.6(13) . . ?
F26 B25 F27 118.9(8) . . ?
F27 B25 F24 108.1(4) . . ?
F27 B25 F28 97.6(11) . . ?
F3 B25 F1 101.7(6) . . ?
F4 B25 F24 113.9(5) . . ?
F4 B25 F1 119.4(7) . . ?
F4 B25 F3 105.8(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
N21 C9 1.485(4) . ?
N21 C23 1.498(4) . ?
N21 C22 1.503(4) . ?
N21 H21 0.89(4) . ?
F24 B25 1.355(4) . ?
F26 B25 1.245(12) . ?
C10 C1 1.435(4) . ?
C10 C9 1.431(4) . ?
C10 C5 1.431(4) . ?
C1 C11 1.489(4) . ?
C1 C2 1.379(4) . ?
C11 C12 1.438(4) . ?
C11 C20 1.367(4) . ?
C9 C8 1.365(4) . ?
C5 C6 1.416(5) . ?
C5 C4 1.413(5) . ?
C12 H12 0.9500 . ?
C12 C13 1.367(4) . ?
C20 H20 0.9500 . ?
C20 C19 1.450(4) . ?
C19 C14 1.413(4) . ?
C19 C18 1.404(4) . ?
C14 C13 1.393(5) . ?
C14 C15 1.441(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.403(5) . ?
C13 H13 0.9500 . ?
C8 H8 0.9500 . ?
C8 C7 1.406(5) . ?
F28 B25 1.377(19) . ?
C6 H6 0.9500 . ?
C6 C7 1.346(6) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C4 H4 0.9500 . ?
C4 C3 1.357(5) . ?
C3 H3 0.9500 . ?
C18 H18 0.9500 . ?
C18 C17 1.368(5) . ?
C15 H15 0.9500 . ?
C15 C16 1.350(5) . ?
C7 H7 0.9500 . ?
C16 H16 0.9500 . ?
C16 C17 1.423(6) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C17 H17 0.9500 . ?
F27 B25 1.317(8) . ?
B25 F1 1.407(7) . ?
B25 F3 1.406(7) . ?
B25 F4 1.320(8) . ?
