CAAC-stabilised 9,10-diboraanthracene: an electronically and structurally flexible platform for small-molecule activation and metal complexation.
Dietz, Maximilian; Arrowsmith, Merle; Braunschweig, Holger; Dalton transactions (Cambridge, England : 2003) 53 (2024) 449–453; doi:10.1039/d3dt03787h

data_7714667
_publ_section_title
;
 CAAC-stabilised 9,10-diboraanthracene: an electronically and structurally
 flexible platform for small-molecule activation and metal complexation.
;
_journal_issue                   2
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              449
_journal_page_last               453
_journal_paper_doi               10.1039/d3dt03787h
_journal_volume                  53
_journal_year                    2024
_chemical_formula_moiety         'C58 H75 B2 N5, 3.5(C6 H6)'
_chemical_formula_sum            'C79 H96 B2 N5'
_chemical_formula_weight         1137.22
_chemical_properties_physical    Air-sensitive,Moisture-sensitive
_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
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2023-11-03
_audit_creation_method           'CIF-fill 1.4o (K.Radacki, 2005-23)'
_audit_update_record
;
2023-11-09 deposited with the CCDC.	2023-12-05 downloaded from the CCDC.
;
_cell_angle_alpha                79.3390(10)
_cell_angle_beta                 86.6270(10)
_cell_angle_gamma                86.6760(10)
_cell_formula_units_Z            2
_cell_length_a                   11.47910(10)
_cell_length_b                   13.02450(10)
_cell_length_c                   22.38830(10)
_cell_measurement_reflns_used    94088
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      77.2470
_cell_measurement_theta_min      2.0110
_cell_volume                     3280.00(4)
_computing_cell_refinement       'CrysAlisPro 1.171.42.68a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.68a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.68a (Rigaku OD, 2022)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)''
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 HPA
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'HyPix 6000'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  \w     28.00  54.00   0.50    0.06    --   50.00  79.00 -34.86   52
  2  \w     26.00  52.00   0.50    0.06    --   47.95  77.00 120.00   52
  3  \w     85.00 117.00   0.50    0.06    --   47.95  19.00  90.00   64
  4  \w     36.00  74.00   0.50    0.06    --   47.95  19.00  90.00   76
  5  \w     45.00  92.00   0.50    0.26    --  107.75 -77.00  90.00   94
  6  \w     38.00 104.00   0.50    0.26    --  107.75 -77.00 150.00  132
  7  \w     35.00  71.00   0.50    0.26    --  107.75 -77.00  30.00   72
  8  \w     36.00  87.00   0.50    0.26    --  107.75 -77.00  60.00  102
  9  \w     44.00  71.00   0.50    0.26    --  107.75 -61.00 -30.00   54
 10  \w     39.00  68.00   0.50    0.26    --  107.75 -77.00 -90.00   58
 11  \w     40.00 106.00   0.50    0.26    --  107.75 -77.00-120.00  132
 12  \w     35.00  70.00   0.50    0.26    --  107.75 -61.00-180.00   70
 13  \w     36.00  68.00   0.50    0.26    --  107.75 -61.00  60.00   64
 14  \w     36.00  70.00   0.50    0.26    --  107.75 -61.00  90.00   68
 15  \w     44.00  70.00   0.50    0.26    --  107.75 -94.00-120.00   52
 16  \w     35.00 111.00   0.50    0.26    --  107.75-125.00-180.00  152
 17  \w     49.00  82.00   0.50    0.06    --   47.95-148.00  73.00   66
 18  \w     37.00  63.00   0.50    0.26    --  107.75-125.00 150.00   52
 19  \w     78.00 109.00   0.50    0.26    --  107.75-125.00 150.00   62
 20  \w     69.00 116.00   0.50    0.26    --  107.75-148.00  73.00   94
 21  \w     36.00 111.00   0.50    0.26    --  107.75-125.00  60.00  150
 22  \w     68.00 111.00   0.50    0.26    --  107.75-125.00  90.00   86
 23  \w     45.00 110.00   0.50    0.26    --  107.75-125.00   0.00  130
 24  \w     72.00 112.00   0.50    0.26    --  107.75-125.00 -90.00   80
 25  \w     70.00 112.00   0.50    0.26    --  107.75-125.00-150.00   84
 26  \w     39.00  64.00   0.50    0.26    --  107.75-125.00 -90.00   50
 27  \w     68.00 110.00   0.50    0.26    --  107.75-123.00-122.00   84
 28  \w     37.00  94.00   0.50    0.06    --   47.95-123.00-122.00  114
 29  \w     35.00 111.00   0.50    0.26    --  107.75-125.00 -30.00  152
 30  \w     74.00 100.00   0.50    0.26    --  107.75 -94.00-120.00   52
 31  \w     54.00 108.00   0.50    0.26    --  107.75-111.00  -6.06  108
 32  \w     69.00 106.00   0.50    0.26    --  107.75 -94.00  60.00   74
 33  \w     36.00  61.00   0.50    0.26    --  107.75-125.00  90.00   50
 34  \w     83.00 108.00   0.50    0.26    --   94.00-114.00 116.04   50
 35  \w    -12.00  18.00   0.50    0.06    --  -47.95   0.00 -90.00   60
 36  \w    -73.00 -48.00   0.50    0.26    --  -86.25 123.00 -42.00   50
 37  \w    -84.00 -11.00   0.50    0.06    --  -47.95 123.00 -42.00  146
 38  \w   -100.00 -29.00   0.50    0.06    --  -47.95   0.00 -90.00  142
 39  \w    -88.00 -63.00   0.50    0.26    --  -86.25 148.00 121.00   50
 40  \w   -101.00 -25.00   0.50    0.06    --  -47.95 148.00 121.00  152
 41  \w    -24.00   6.00   0.50    0.06    --   10.00 103.00  93.84   60
 42  \w      8.00  33.00   0.50    0.06    --   38.00  93.00 172.46   50
 43  \w      7.00  32.00   0.50    0.06    --   38.00  94.00  46.49   50
 44  \w     -8.00  17.00   0.50    0.06    --   26.00 101.00-100.62   50
 45  \w     17.00  42.00   0.50    0.06    --   46.00  90.00-111.61   50
 46  \w      8.00  33.00   0.50    0.06    --   38.00  92.00   5.89   50
 47  \w     -9.00  38.00   0.50    0.06    --   18.00  89.00 175.74   94
 48  \w     30.00  55.00   0.50    0.06    --   54.00  79.00 149.06   50
 49  \w     47.00  73.00   0.50    0.06    --   70.00  77.00 141.68   52
 50  \w     42.00  68.00   0.50    0.06    --   66.00  79.00  86.09   52
 51  \w     39.00  65.00   0.50    0.06    --   62.00  79.00 -58.41   52
 52  \w     42.00  73.00   0.50    0.06    --   66.00  79.00 -41.88   62
 53  \w     70.00 110.00   0.50    0.26    --   94.00  79.00 -17.58   80
 54  \w    144.00 176.00   0.50    0.26    --  107.75  77.00  30.00   64
 55  \w     85.00 124.00   0.50    0.26    --  107.75  77.00  30.00   78
 56  \w     85.00 158.00   0.50    0.26    --  107.75  77.00 -90.00  146
 57  \w    126.00 177.00   0.50    0.26    --  107.75  77.00-120.00  102
 58  \w     86.00 121.00   0.50    0.26    --  107.75  77.00-120.00   70
 59  \w     85.00 169.00   0.50    0.26    --  107.75  77.00-180.00  168
 60  \w    121.00 178.00   0.50    0.26    --  107.75  77.00 -30.00  114
 61  \w     85.00 168.00   0.50    0.26    --  107.75  77.00 -60.00  166
 62  \w     85.00 110.00   0.50    0.26    --  107.75  77.00 -30.00   50
 63  \w    137.00 163.00   0.50    0.26    --  107.75  77.00  90.00   52
 64  \w     86.00 178.00   0.50    0.26    --  107.75  77.00  60.00  184
 65  \w     85.00 111.00   0.50    0.26    --  107.75  77.00  90.00   52
 66  \w     85.00 123.00   0.50    0.26    --  107.75  77.00 150.00   76
 67  \w    131.00 157.00   0.50    0.26    --  107.75  77.00 150.00   52
 68  \w    142.00 171.00   0.50    0.26    --  107.75  77.00 120.00   58
 69  \w     85.00 125.00   0.50    0.26    --  107.75  77.00 120.00   80
 70  \w    119.00 145.00   0.50    0.26    --  107.75  77.00   0.00   52
 71  \w     86.00 112.00   0.50    0.26    --  107.75  77.00   0.00   52
 72  \w    137.00 163.00   0.50    0.26    --  107.75  77.00-150.00   52
 73  \w    116.00 142.00   0.50    0.26    --   94.00  76.00-173.03   52
 74  \w     72.00 111.00   0.50    0.26    --   94.00  76.00-173.03   78
 75  \w     85.00 120.00   0.50    0.26    --  107.75  77.00-150.00   70
 76  \w     40.00  66.00   0.50    0.06    --   62.00  75.00-173.60   52
 77  \w     87.00 138.00   0.50    0.26    --  107.75  73.00 -68.42  102
 78  \w    153.00 178.00   0.50    0.26    --  107.75  73.00 -68.42   50
 79  \w     91.00 121.00   0.50    0.26    --  107.75  61.00-120.00   60
 80  \w    138.00 178.00   0.50    0.26    --  107.75  72.00 104.20   80
 81  \w     89.00 132.00   0.50    0.26    --  107.75  72.00 104.20   86
 82  \w     74.00 100.00   0.50    0.26    --   94.00  71.00 100.67   52
 83  \w     91.00 126.00   0.50    0.26    --  107.75  61.00 150.00   70
 84  \w     99.00 160.00   0.50    0.26    --  107.75  61.00 120.00  122
 85  \w    128.00 175.00   0.50    0.26    --  102.00  61.00  13.72   94
 86  \w     86.00 113.00   0.50    0.26    --  102.00  61.00  13.72   54
 87  \w     91.00 168.00   0.50    0.26    --  107.75  61.00   0.00  154
 88  \w     91.00 134.00   0.50    0.26    --  107.75  61.00 -30.00   86
 89  \w     92.00 165.00   0.50    0.26    --  107.75  61.00  30.00  146
 90  \w     91.00 156.00   0.50    0.26    --  107.75  61.00 -90.00  130
 91  \w     91.00 166.00   0.50    0.26    --  107.75  61.00-150.00  150
 92  \w     91.00 154.00   0.50    0.26    --  107.75  61.00-180.00  126
 93  \w    126.00 152.00   0.50    0.26    --  107.75  61.00-120.00   52
 94  \w    139.00 165.00   0.50    0.26    --  107.75  61.00  60.00   52
 95  \w     91.00 174.00   0.50    0.26    --  107.75  61.00  90.00  166
 96  \w     91.00 128.00   0.50    0.26    --  107.75  61.00  60.00   74
 97  \w    128.00 160.00   0.50    0.26    --  107.75  45.00  60.00   64
 98  \w    131.00 166.00   0.50    0.26    --  107.75  45.00 -60.00   70
 99  \w    123.00 172.00   0.50    0.26    --  107.75  45.00-120.00   98
 100  \w     98.00 173.00   0.50    0.26    --  107.75  15.00-150.00  150
 101  \w     99.00 124.00   0.50    0.26    --  107.75 123.00 -42.00   50
 102  \w     96.00 143.00   0.50    0.26    --  107.75 125.00 -60.00   94
 103  \w    149.00 177.00   0.50    0.26    --  107.75 125.00 -60.00   56
 104  \w     99.00 124.00   0.50    0.26    --  107.75 148.00 121.00   50
 105  \w    103.00 147.00   0.50    0.26    --  107.75 125.00 120.00   88
 106  \w    152.00 177.00   0.50    0.26    --  107.75 125.00 120.00   50
 107  \w    -63.00 -25.00   0.50    0.06    --  -47.95 -77.00 120.00   76
 108  \w   -116.00 -74.00   0.50    0.06    --  -47.95 -77.00 120.00   84
 109  \w   -113.00 -88.00   0.50    0.06    --  -47.95-148.00  73.00   50
 110  \w   -128.00-103.00   0.50    0.26    --  -86.25-148.00  73.00   50
 111  \w   -141.00-116.00   0.50    0.26    --  -86.25-123.00-122.00   50
 112  \w    -51.00 -25.00   0.50    0.06    --  -47.95 -77.00 -30.00   52
 113  \w    -55.00 -30.00   0.50    0.06    --  -54.00 -80.00  54.13   50
 114  \w    -63.00 -38.00   0.50    0.06    --  -62.00 -80.00 116.95   50
 115  \w   -120.00 -94.00   0.50    0.06    --  -62.00 -80.00 116.95   52
 116  \w    -77.00 -46.00   0.50    0.26    --  -70.00 -80.00 -86.95   62
 117  \w    -87.00 -62.00   0.50    0.26    --  -86.25 -79.00-133.73   50
 118  \w    -63.00 -35.00   0.50    0.06    --  -58.00 -79.00-154.88   56
 119  \w    -94.00 -62.00   0.50    0.26    --  -86.25 -79.00-178.20   64
 120  \w   -118.00 -63.00   0.50    0.26    --  -86.25 -78.00-155.87  110
 121  \w   -131.00 -89.00   0.50    0.06    --  -58.00 -79.00-154.88   84
 122  \w   -123.00 -97.00   0.50    0.06    --  -58.00 -78.00-129.82   52
 123  \w    -61.00 -35.00   0.50    0.06    --  -58.00 -78.00-129.82   52
 124  \w    -61.00 -35.00   0.50    0.06    --  -58.00 -78.00  -5.39   52
 125  \w    -99.00 -62.00   0.50    0.26    --  -86.25 -79.00  -9.15   74
 126  \w    -88.00 -59.00   0.50    0.26    --  -82.00 -78.00 -39.26   58
 127  \w   -101.00 -62.00   0.50    0.26    --  -86.25 -79.00  11.26   78
 128  \w    -89.00 -63.00   0.50    0.26    --  -86.25 -78.00  39.35   52
 129  \w    -87.00 -62.00   0.50    0.26    --  -86.25 -79.00  85.70   50
 130  \w    -88.00 -63.00   0.50    0.26    --  -86.25 -77.00 120.00   50
 131  \w    -60.00 -35.00   0.50    0.06    --  -58.00 -78.00  37.44   50
 132  \w    -90.00 -63.00   0.50    0.26    --  -86.25 -77.00 -90.00   54
 133  \w    -90.00 -63.00   0.50    0.26    --  -86.25 -77.00 -60.00   54
 134  \w   -108.00 -63.00   0.50    0.26    --  -86.25 -77.00-120.00   90
 135  \w    -90.00 -64.00   0.50    0.26    --  -86.25 -78.00 -47.98   52
 136  \w    -81.00 -55.00   0.50    0.26    --  -78.00 -76.00-117.50   52
 137  \w    -92.00 -63.00   0.50    0.26    --  -86.25 -77.00  23.58   58
 138  \w   -126.00 -78.00   0.50    0.06    --  -54.00 -76.00 -78.04   96
 139  \w    -92.00 -63.00   0.50    0.26    --  -86.25 -77.00  60.00   58
 140  \w    -92.00 -63.00   0.50    0.26    --  -86.25 -77.00 150.00   58
 141  \w    -97.00 -60.00   0.50    0.26    --  -82.00 -76.00 164.64   74
 142  \w    -72.00 -36.00   0.50    0.06    --  -58.00 -76.00 166.50   72
 143  \w    -76.00 -51.00   0.50    0.26    --  -74.00 -76.00 103.12   50
 144  \w    -78.00 -52.00   0.50    0.26    --  -74.00 -75.00  35.25   52
 145  \w    -78.00 -52.00   0.50    0.26    --  -74.00 -75.00   5.20   52
 146  \w    -93.00 -40.00   0.50    0.06    --  -62.00 -75.00 -28.88  106
 147  \w    -70.00 -33.00   0.50    0.06    --  -54.00 -76.00 -78.04   74
 148  \w    -77.00 -52.00   0.50    0.26    --  -74.00 -74.00-152.63   50
 149  \w    -90.00 -64.00   0.50    0.26    --  -86.25 -75.00-105.45   52
 150  \w    -93.00 -57.00   0.50    0.26    --  -78.00 -73.00-167.12   72
 151  \w    -82.00 -56.00   0.50    0.26    --  -78.00 -74.00  57.66   52
 152  \w    -91.00 -65.00   0.50    0.26    --  -86.25 -74.00 134.97   52
 153  \w    -81.00 -56.00   0.50    0.26    --  -78.00 -75.00 169.31   50
 154  \w    -89.00 -56.00   0.50    0.26    --  -78.00 -74.00 175.12   66
 155  \w    -83.00 -57.00   0.50    0.26    --  -78.00 -73.00  72.79   52
 156  \w    -92.00 -66.00   0.50    0.26    --  -86.25 -71.00  96.24   52
 157  \w    -90.00 -65.00   0.50    0.26    --  -86.25 -72.00 -80.28   50
 158  \w    -73.00 -47.00   0.50    0.06    --  -66.00 -68.00-135.11   52
 159  \w    -87.00 -61.00   0.50    0.26    --  -82.00 -72.00-137.21   52
 160  \w   -136.00-110.00   0.50    0.26    --  -86.25 -72.00 -80.28   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy-S'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
;
 CrysAlisPro convention (1999,Acta A55,543-557)
;
_diffrn_orient_matrix_UB_11      0.1302815000
_diffrn_orient_matrix_UB_12      -0.0300301000
_diffrn_orient_matrix_UB_13      0.0094726000
_diffrn_orient_matrix_UB_21      0.0222261000
_diffrn_orient_matrix_UB_22      0.0076154000
_diffrn_orient_matrix_UB_23      -0.0691791000
_diffrn_orient_matrix_UB_31      0.0254584000
_diffrn_orient_matrix_UB_32      0.1164481000
_diffrn_orient_matrix_UB_33      -0.0062516000
_diffrn_radiation_monochromator  'multi-layer mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_xray_symbol    K-L~2,3~
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_unetI/netI     0.0153
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            134016
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.071
_diffrn_reflns_theta_min         2.010
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet X-ray Source'
_exptl_absorpt_coefficient_mu    0.495
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.613
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
 CrysAlisPro 1.171.42.68a (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            yellow
_exptl_crystal_density_diffrn    1.151
_exptl_crystal_description       block
_exptl_crystal_F_000             1230
_exptl_crystal_preparation
;
 For data collection the crystal was immersed in a film of perfluoropolyether 
 oil, mounted on a polyimide loop and transferred to stream of cold nitrogen 
 (Oxford Cryostream 800).
;
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: benzene'
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.315
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.856
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     791
_refine_ls_number_reflns         12419
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.856
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0359
_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/[\s^2^(Fo^2^)+(0.0603P)^2^+1.6054P] where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0938
_refine_ls_wR_factor_ref         0.0962
_reflns_Friedel_coverage         0.000
_reflns_number_gt                11545
_reflns_number_total             12419
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3dt03787h2.cif
_cod_data_source_block           MaDi223_MaDi_a_(DBA)N3Ph
_cod_depositor_comments
'Adding full bibliography for 7714662--7714667.cif.'
_cod_database_code               7714667
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_min   0.899
_shelx_estimated_absorpt_t_max   0.961
_shelx_res_checksum              9659