Accessing unusual heterocycles: ring expansion of benzoborirenes by formal cycloaddition reactions.
Sindlinger, Marvin; Ströbele, Markus; Grunenberg, Jörg; Bettinger, Holger F.; Chemical science 14 (2023) 10478–10487; doi:10.1039/d3sc03433j

data_1569872
_publ_section_title
;
 Accessing unusual heterocycles: ring expansion of benzoborirenes by
 formal cycloaddition reactions.
;
_journal_issue                   38
_journal_name_full               'Chemical science'
_journal_page_first              10478
_journal_page_last               10487
_journal_paper_doi               10.1039/d3sc03433j
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C52 H71 B N2, C7 H8'
_chemical_formula_sum            'C59 H79 B N2'
_chemical_formula_weight         827.05
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-11-16
_audit_creation_method
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_audit_update_record
;
2022-11-16 deposited with the CCDC.	2023-08-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.8700(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.8427(2)
_cell_length_b                   10.73860(10)
_cell_length_c                   22.3596(2)
_cell_measurement_reflns_used    30956
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      79.5830
_cell_measurement_theta_min      3.9870
_cell_volume                     5167.04(8)
_computing_cell_refinement       'CrysAlisPro 1.171.42.70a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.70a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.70a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (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      149.99(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 1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -70.00  -1.00   0.50    2.00    --  -49.70  80.00 112.00  138
  2  \w    -14.00  52.00   0.50    2.00    --   49.70 -80.00 -10.00  132
  3  \w    -89.00 -64.00   0.50    5.00    --  -90.00  80.00 112.00   50
  4  \w   -144.00-119.00   0.50    5.00    --  -90.00 -80.00 -10.00   50
  5  \w    101.00 171.00   0.50    5.00    --  111.50  80.00 112.00  140
  6  \w     79.00 133.00   0.50    5.00    --  111.50 -80.00 -10.00  108
  7  \w   -114.00 -73.00   0.50    2.00    --  -49.70-125.00  60.00   82
  8  \w   -118.00 -93.00   0.50    2.00    --  -49.70-125.00  90.00   50
  9  \w   -111.00 -76.00   0.50    2.00    --  -49.70-125.00  30.00   70
 10  \w    -18.00  17.00   0.50    2.00    --  -49.70  19.00-150.00   70
 11  \w    -25.00  22.00   0.50    2.00    --  -49.70  19.00-120.00   94
 12  \w    -50.00 -18.00   0.50    5.00    --  -90.00  45.00 -60.00   64
 13  \w     41.00  66.00   0.50    5.00    --  111.50 -61.00-150.00   50
 14  \w    103.00 129.00   0.50    5.00    --  111.50  61.00  90.00   52
 15  \w     42.00  70.00   0.50    5.00    --  111.50 -61.00  90.00   56
 16  \w    125.00 169.00   0.50    5.00    --  111.50 125.00 -30.00   88
 17  \w    149.00 178.00   0.50    5.00    --  111.50  61.00  90.00   58
 18  \w     41.00  77.00   0.50    5.00    --  111.50 -77.00  60.00   72
 19  \w    108.00 159.00   0.50    5.00    --  111.50  30.00 -60.00  102
 20  \w    111.00 162.00   0.50    5.00    --  111.50  61.00-120.00  102
 21  \w    109.00 135.00   0.50    5.00    --  111.50  45.00   0.00   52
 22  \w    116.00 142.00   0.50    5.00    --  111.50  61.00 150.00   52
 23  \w     76.00 114.00   0.50    5.00    --  111.50   0.00  60.00   76
 24  \w    130.00 158.00   0.50    5.00    --  111.50  77.00   0.00   56
 25  \w     44.00  70.00   0.50    5.00    --  111.50 -61.00 150.00   52
 26  \w    112.00 178.00   0.50    5.00    --  111.50  61.00-150.00  132
 27  \w     98.00 167.00   0.50    5.00    --  111.50  61.00-180.00  138
 28  \w    113.00 139.00   0.50    5.00    --  111.50  61.00  30.00   52
 29  \w     41.00  66.00   0.50    5.00    --  111.50 -61.00  30.00   50
 30  \w     98.00 127.00   0.50    5.00    --  111.50  77.00   0.00   58
 31  \w     74.00 100.00   0.50    5.00    --  111.50 -77.00   0.00   52
 32  \w    109.00 154.00   0.50    5.00    --  111.50 125.00 -90.00   90
 33  \w     62.00 106.00   0.50    5.00    --  111.50 -94.00   0.00   88
 34  \w    135.00 177.00   0.50    5.00    --  111.50  15.00-150.00   84
 35  \w    141.00 175.00   0.50    5.00    --  111.50  77.00  60.00   68
 36  \w     50.00  76.00   0.50    5.00    --  111.50 -94.00  90.00   52
 37  \w    102.00 128.00   0.50    5.00    --  111.50  77.00  60.00   52
 38  \w     41.00  95.00   0.50    5.00    --  111.50 -77.00 120.00  108
 39  \w    102.00 177.00   0.50    5.00    --  111.50  77.00 150.00  150
 40  \w     44.00  70.00   0.50    5.00    --  111.50 -60.00  53.14   52
 41  \w     72.00 126.00   0.50    5.00    --  111.50 -80.00  82.27  108
 42  \w     43.00 111.00   0.50    5.00    --  111.50-125.00  30.00  136
 43  \w    114.00 147.00   0.50    5.00    --  111.50  30.00-120.00   66
 44  \w    110.00 138.00   0.50    5.00    --  111.50  30.00  60.00   56
 45  \w    153.00 178.00   0.50    5.00    --  111.50  30.00  60.00   50
 46  \w    110.00 135.00   0.50    5.00    --  111.50  30.00  90.00   50
 47  \w    119.00 152.00   0.50    5.00    --  111.50  30.00 120.00   66
 48  \w    139.00 165.00   0.50    5.00    --  111.50  15.00  60.00   52
 49  \w     99.00 144.00   0.50    5.00    --  111.50  61.00 -30.00   90
 50  \w    142.00 168.00   0.50    5.00    --  111.50 125.00-180.00   52
 51  \w     42.00  68.00   0.50    5.00    --  111.50 -61.00   0.00   52
 52  \w    -56.00 -30.00   0.50    2.00    --  -49.70 -77.00 -60.00   52
 53  \w    -64.00 -31.00   0.50    2.00    --  -49.70 -77.00  60.00   66
 54  \w    -79.00 -44.00   0.50    2.00    --  -49.70 -37.00-180.00   70
 55  \w    -61.00 -30.00   0.50    2.00    --  -49.70 -77.00-120.00   62
 56  \w   -113.00 -49.00   0.50    2.00    --  -49.70 -25.00 104.75  128
 57  \w    -91.00 -45.00   0.50    2.00    --  -49.70 -40.00 -90.84   92
 58  \w    -56.00 -30.00   0.50    2.00    --  -49.70 -77.00   0.00   52
 59  \w    -56.00 -31.00   0.50    2.00    --  -49.70 -77.00  30.00   50
 60  \w    -69.00 -39.00   0.50    2.00    --  -49.70 -60.00 125.38   60
 61  \w   -113.00 -88.00   0.50    2.00    --  -49.70 -77.00-150.00   50
 62  \w    -84.00 -45.00   0.50    2.00    --  -49.70 -37.00   0.00   78
 63  \w    -68.00 -30.00   0.50    2.00    --  -49.70 -77.00 -90.00   76
 64  \w    -55.00 -30.00   0.50    2.00    --  -49.70 -77.00 120.00   50
 65  \w    -69.00 -41.00   0.50    2.00    --  -49.70 -55.00 -83.33   56
 66  \w    -80.00 -30.00   0.50    2.00    --  -49.70 -77.00  90.00  100
 67  \w    -64.00 -39.00   0.50    2.00    --  -49.70 -54.00 144.99   50
 68  \w    -57.00 -31.00   0.50    2.00    --  -49.70 -77.00 -30.00   52
 69  \w    -69.00 -38.00   0.50    2.00    --  -49.70 -56.00 -21.36   62
 70  \w    -57.00 -30.00   0.50    2.00    --  -49.70 -77.00 150.00   54
 71  \w   -112.00 -85.00   0.50    2.00    --  -49.70 -54.00 144.99   54
 72  \w    -58.00 -30.00   0.50    2.00    --  -49.70 -77.00-150.00   56
 73  \w    -55.00 -30.00   0.50    2.00    --  -49.70 -77.00-180.00   50
 74  \w     46.00  75.00   0.50    2.00    --   49.70  37.00   0.00   58
 75  \w     38.00  79.00   0.50    2.00    --   49.70  57.00 120.00   82
 76  \w     36.00  92.00   0.50    2.00    --   49.70-125.00   0.00  112
 77  \w      3.00  46.00   0.50    2.00    --   49.70   0.00  30.00   86
 78  \w     44.00  70.00   0.50    2.00    --   49.70  37.00  90.00   52
 79  \w    -99.00 -74.00   0.50    5.00    --  -90.00 -69.00-117.56   50
 80  \w    -98.00 -72.00   0.50    5.00    --  -90.00 -73.00  44.49   52
 81  \w   -100.00 -70.00   0.50    5.00    --  -90.00 -77.00 120.00   60
 82  \w    -98.00 -72.00   0.50    5.00    --  -90.00 -76.00 -95.56   52
 83  \w    -96.00 -70.00   0.50    5.00    --  -90.00 -77.00  60.00   52
 84  \w    -96.00 -71.00   0.50    5.00    --  -90.00 -75.00-176.78   50
 85  \w    -95.00 -70.00   0.50    5.00    --  -90.00 -77.00 -20.90   50
 86  \w    -96.00 -70.00   0.50    5.00    --  -90.00 -77.00  30.00   52
 87  \w    -96.00 -70.00   0.50    5.00    --  -90.00 -77.00-150.00   52
 88  \w    -97.00 -71.00   0.50    5.00    --  -90.00 -75.00 174.35   52
 89  \w    -99.00 -73.00   0.50    5.00    --  -90.00 -70.00 124.19   52
 90  \w    -98.00 -72.00   0.50    5.00    --  -90.00 -72.00 146.11   52
 91  \w    -96.00 -70.00   0.50    5.00    --  -90.00 -77.00-136.79   52
 92  \w   -100.00 -74.00   0.50    5.00    --  -90.00 -67.00 -54.46   52
 93  \w    -95.00 -70.00   0.50    5.00    --  -90.00 -77.00-120.00   50
 94  \w    -98.00 -73.00   0.50    5.00    --  -90.00 -71.00 135.51   50
 95  \w    -95.00 -70.00   0.50    5.00    --  -90.00 -77.00 -90.00   50
 96  \w    -99.00 -72.00   0.50    5.00    --  -90.00 -72.00  64.26   54
 97  \w    -96.00 -70.00   0.50    5.00    --  -90.00 -77.00  90.00   52
 98  \w   -161.00-135.00   0.50    5.00    --  -90.00 -77.00 -60.00   52
 99  \w    -96.00 -70.00   0.50    5.00    --  -90.00 -77.00 -60.00   52
100  \w    -96.00 -70.00   0.50    5.00    --  -90.00 -77.00   0.00   52
101  \w    -99.00 -73.00   0.50    5.00    --  -90.00 -71.00 -76.27   52
102  \w    -96.00 -70.00   0.50    5.00    --  -90.00 -77.00   6.45   52
103  \w    -96.00 -71.00   0.50    5.00    --  -90.00 -76.00 -53.62   50
104  \w    -99.00 -73.00   0.50    5.00    --  -90.00 -70.00 -20.41   52
105  \w    -98.00 -73.00   0.50    5.00    --  -90.00 -71.00  35.80   50
106  \w    -96.00 -70.00   0.50    5.00    --  -90.00 -77.00-159.18   52
107  \w    -98.00 -72.00   0.50    5.00    --  -90.00 -73.00  76.45   52
108  \w   -152.00-126.00   0.50    5.00    --  -90.00 -76.00 -53.62   52
109  \w    -97.00 -72.00   0.50    5.00    --  -90.00 -72.00 155.78   50
110  \w   -100.00 -74.00   0.50    5.00    --  -90.00 -67.00   9.07   52
111  \w   -122.00 -72.00   0.50    5.00    --  -90.00 -74.00 101.64  100
112  \w    -97.00 -71.00   0.50    5.00    --  -90.00 -76.00 -33.14   52
113  \w    133.00 159.00   0.50    5.00    --  111.50  77.00 -90.00   52
114  \w    100.00 138.00   0.50    5.00    --  111.50 125.00  90.00   76
115  \w     92.00 124.00   0.50    5.00    --  111.50  77.00 -90.00   64
116  \w    106.00 156.00   0.50    5.00    --  111.50  45.00 120.00  100
117  \w    125.00 160.00   0.50    5.00    --  111.50 125.00 120.00   70
118  \w    115.00 167.00   0.50    5.00    --  111.50  45.00  90.00  104
119  \w    146.00 171.00   0.50    5.00    --  111.50  45.00  30.00   50
120  \w    116.00 142.00   0.50    5.00    --  111.50  45.00  30.00   52
121  \w     93.00 157.00   0.50    5.00    --  111.50  77.00-120.00  128
122  \w    147.00 174.00   0.50    5.00    --  111.50  77.00-180.00   54
123  \w     45.00  70.00   0.50    5.00    --  111.50 -61.00 -90.00   50
124  \w     92.00 123.00   0.50    5.00    --  111.50  77.00-180.00   62
125  \w     58.00 108.00   0.50    5.00    --  111.50-106.00  44.34  100
126  \w    143.00 170.00   0.50    5.00    --  111.50  77.00 -60.00   54
127  \w     86.00 111.00   0.50    5.00    --  111.50-125.00-180.00   50
128  \w     92.00 129.00   0.50    5.00    --  111.50  77.00 -60.00   74
129  \w     99.00 125.00   0.50    5.00    --  111.50  61.00  60.00   52
130  \w     92.00 118.00   0.50    5.00    --  111.50  77.00   0.00   52
131  \w    133.00 176.00   0.50    5.00    --  111.50  77.00 120.00   86
132  \w     83.00 108.00   0.50    5.00    --  111.50-106.00-150.59   50
133  \w     93.00 121.00   0.50    5.00    --  111.50  77.00 120.00   56
134  \w    140.00 167.00   0.50    5.00    --  111.50  61.00   0.00   54
135  \w     48.00  74.00   0.50    5.00    --  111.50-106.00-150.59   52
136  \w    100.00 128.00   0.50    5.00    --  111.50  61.00   0.00   56
137  \w     41.00 105.00   0.50    5.00    --  111.50 -94.00 -60.00  128
138  \w     92.00 117.00   0.50    5.00    --  111.50  77.00 150.00   50
139  \w    138.00 178.00   0.50    5.00    --  111.50  77.00  30.00   80
140  \w     92.00 127.00   0.50    5.00    --  111.50  77.00  30.00   70
141  \w    117.00 166.00   0.50    5.00    --  111.50 125.00  30.00   98
142  \w    153.00 178.00   0.50    5.00    --  111.50  61.00-120.00   50
143  \w    134.00 163.00   0.50    5.00    --  111.50  15.00-180.00   58
144  \w     98.00 124.00   0.50    5.00    --  111.50  61.00 120.00   52
145  \w     46.00  91.00   0.50    5.00    --  111.50 -94.00-180.00   90
146  \w     98.00 143.00   0.50    5.00    --  111.50  61.00 -90.00   90
147  \w    101.00 127.00   0.50    5.00    --  111.50  61.00-120.00   52
148  \w    151.00 178.00   0.50    5.00    --  111.50  30.00 -30.00   54
149  \w     98.00 141.00   0.50    5.00    --  111.50  61.00 -60.00   86
150  \w    109.00 146.00   0.50    5.00    --  111.50  30.00 -30.00   74
151  \w     92.00 117.00   0.50    5.00    --  111.50  77.00  60.00   50
152  \w    137.00 163.00   0.50    5.00    --  111.50  61.00  30.00   52
153  \w     98.00 124.00   0.50    5.00    --  111.50  61.00  30.00   52
154  \w     86.00 111.00   0.50    5.00    --  111.50-125.00 -60.00   50
155  \w    151.00 177.00   0.50    5.00    --  111.50  77.00   0.00   52
156  \w     81.00 106.00   0.50    5.00    --  111.50 -94.00 150.00   50
157  \w     43.00  73.00   0.50    5.00    --  111.50-125.00-180.00   60
158  \w     42.00  68.00   0.50    5.00    --  111.50 -94.00 150.00   52
159  \w    125.00 164.00   0.50    5.00    --  111.50 125.00 150.00   78
160  \w    113.00 143.00   0.50    5.00    --  111.50  30.00-150.00   60
161  \w    148.00 174.00   0.50    5.00    --  111.50  30.00-150.00   52
162  \w     79.00 105.00   0.50    5.00    --  111.50 -94.00 -30.00   52
163  \w     41.00  72.00   0.50    5.00    --  111.50 -94.00 -30.00   62
164  \w     41.00  99.00   0.50    5.00    --  111.50 -77.00-120.00  116
165  \w     41.00  67.00   0.50    5.00    --  111.50 -60.00-157.54   52
166  \w    136.00 173.00   0.50    5.00    --  111.50  77.00  90.00   74
167  \w     80.00 105.00   0.50    5.00    --  111.50 -98.00 122.22   50
168  \w     92.00 117.00   0.50    5.00    --  111.50  77.00  90.00   50
169  \w     79.00 105.00   0.50    5.00    --  111.50 -94.00  60.00   52
170  \w     42.00  70.00   0.50    5.00    --  111.50 -98.00 122.22   56
171  \w    130.00 156.00   0.50    5.00    --  111.50  61.00 150.00   52
172  \w     98.00 124.00   0.50    5.00    --  111.50  61.00 150.00   52
173  \w     82.00 107.00   0.50    5.00    --  111.50-104.00-146.22   50
174  \w    111.00 137.00   0.50    5.00    --  111.50  30.00   0.00   52
175  \w    144.00 171.00   0.50    5.00    --  111.50 125.00  90.00   54
176  \w     93.00 118.00   0.50    5.00    --  111.50  77.00-150.00   50
177  \w    141.00 174.00   0.50    5.00    --  111.50  77.00-150.00   66
178  \w    112.00 138.00   0.50    5.00    --  111.50 125.00-120.00   52
179  \w    103.00 129.00   0.50    5.00    --  111.50  61.00-150.00   52
180  \w     42.00  76.00   0.50    5.00    --  111.50-104.00-146.22   68
181  \w     70.00 106.00   0.50    5.00    --  111.50 -94.00-120.00   72
182  \w    100.00 132.00   0.50    5.00    --  111.50 -82.00  44.89   64
183  \w    142.00 171.00   0.50    5.00    --  111.50  77.00 -30.00   58
184  \w     92.00 117.00   0.50    5.00    --  111.50  77.00 -30.00   50
185  \w    148.00 175.00   0.50    5.00    --  111.50  30.00   0.00   54
186  \w     58.00 130.00   0.50    5.00    --  111.50 -88.00-156.13  144
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0511035000
_diffrn_orient_matrix_UB_12      -0.0775898000
_diffrn_orient_matrix_UB_13      -0.0220794000
_diffrn_orient_matrix_UB_21      -0.0491148000
_diffrn_orient_matrix_UB_22      -0.0957815000
_diffrn_orient_matrix_UB_23      -0.0281132000
_diffrn_orient_matrix_UB_31      -0.0100968000
_diffrn_orient_matrix_UB_32      0.0733531000
_diffrn_orient_matrix_UB_33      -0.0601167000
_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  0.0563
_diffrn_reflns_av_unetI/netI     0.0174
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            211996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.243
_diffrn_reflns_theta_min         4.014
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.445
_exptl_absorpt_correction_T_max  0.94185
_exptl_absorpt_correction_T_min  0.94185
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.70a (Rigaku Oxford Diffraction, 2022)
Spherical absorption correction
using equivalent radius and absorption coefficient.
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.063
_exptl_crystal_description       sphere
_exptl_crystal_F_000             1808
_exptl_crystal_size_max          0.242
_exptl_crystal_size_mid          0.199
_exptl_crystal_size_min          0.122
_exptl_crystal_size_rad          0.087
_refine_diff_density_max         0.469
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     691
_refine_ls_number_reflns         9448
_refine_ls_number_restraints     171
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0498
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0763P)^2^+2.1664P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1368
_refine_ls_wR_factor_ref         0.1381
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8996
_reflns_number_total             9448
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc03433j2.cif
_cod_data_source_block           ms281022
_cod_depositor_comments
'Adding full bibliography for 1569871--1569873.cif.'
_cod_database_code               1569872
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C59 H79 B N2'
_shelx_estimated_absorpt_t_max   0.948
_shelx_estimated_absorpt_t_min   0.900
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C54-C59 \\sim C54A-C59A
 with sigma of 0.02
 C54-C53 \\sim C54A-C53A
 with sigma of 0.02
 C59-C53 \\sim C59A-C53A
 with sigma of 0.04
 C55-C53 \\sim C55A-C53A
 with sigma of 0.04
 C54-C55 \\sim C54A-C55A
 with sigma of 0.02
 C57-C55 \\sim C57A-C55A
 with sigma of 0.04
 C58-C57 \\sim C58A-C57A
 with sigma of 0.02
 C58-C59 \\sim C58A-C59A
 with sigma of 0.02
 C54-C58 \\sim C54A-C58A
 with sigma of 0.04
 C58-C56 \\sim C58A-C56A
 with sigma of 0.04
 C54-C56 \\sim C54A-C56A
 with sigma of 0.04
 C57-C56 \\sim C57A-C56A
 with sigma of 0.02
 C59-C55 \\sim C59A-C55A
 with sigma of 0.04
 C55-C56 \\sim C55A-C56A
 with sigma of 0.02
 C57-C59 \\sim C57A-C59A
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Uanis(C53A) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(C34) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(C33) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
4. Rigid body (RIGU) restrains
 C25, C26, C32, C33, C34
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C25, C25A, C26, C26A, C32, C32A, C33, C33A, C34, C34A
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C53, C53A, C54, C54A, C55, C55A, C56, C56A, C57, C57A, C58, C58A, C59, C59A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C25A, C26A, C32A, C33A, C34A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(C53A)=Sof(H53D)=Sof(H53E)=Sof(H53F)=Sof(C54A)=Sof(C55A)=Sof(H55A)=
 Sof(C56A)=Sof(H56A)=Sof(C57A)=Sof(H57A)=Sof(C58A)=Sof(H58A)=Sof(C59A)=
 Sof(H59A)=1-FVAR(1)
 Sof(C53)=Sof(H53A)=Sof(H53B)=Sof(H53C)=Sof(C54)=Sof(C55)=Sof(H55)=Sof(C56)=
 Sof(H56)=Sof(C57)=Sof(H57)=Sof(C58)=Sof(H58)=Sof(C59)=Sof(H59)=FVAR(1)
 Sof(C25)=Sof(H25)=Sof(C26)=Sof(H27A)=Sof(C32)=Sof(H32)=Sof(C33)=Sof(H33A)=
 Sof(H33B)=Sof(H33C)=Sof(C34)=Sof(H34A)=Sof(H34B)=Sof(H34C)=1-FVAR(2)
 Sof(C25A)=Sof(H25A)=Sof(C26A)=Sof(H27)=Sof(C32A)=Sof(H32A)=Sof(C33A)=
 Sof(H33D)=Sof(H33E)=Sof(H33F)=Sof(C34A)=Sof(H34D)=Sof(H34E)=Sof(H34F)=FVAR(2)
6.a Ternary CH refined with riding coordinates:
 C29(H29), C32(H32), C32A(H32A), C35(H35), C44(H44), C47(H47), C50(H50)
6.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C19(H19), C20(H20), C21(H21), C25(H25),
 C25A(H25A), C27(H27), C27(H27A), C40(H40), C42(H42), C55(H55), C55A(H55A),
 C56(H56), C56A(H56A), C57(H57), C57A(H57A), C58(H58), C58A(H58A), C59(H59),
 C59A(H59A)
6.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C14(H14A,H14B,
 H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C30(H30A,H30B,H30C), C31(H31A,
 H31B,H31C), C33(H33A,H33B,H33C), C33A(H33D,H33E,H33F), C34(H34A,H34B,H34C),
 C34A(H34D,H34E,H34F), C36(H36A,H36B,H36C), C37(H37A,H37B,H37C), C45(H45A,H45B,
 H45C), C46(H46A,H46B,H46C), C48(H48A,H48B,H48C), C49(H49A,H49B,H49C), C51(H51A,
 H51B,H51C), C52(H52A,H52B,H52C), C53(H53A,H53B,H53C), C53A(H53D,H53E,H53F)
;
_shelx_res_checksum              89559
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 5.629
_oxdiff_exptl_absorpt_empirical_full_min 0.306