Ring expansion of an antiaromatic beryllole: synthesis of novel five-, seven- and nine-membered beryllacycles.
Tröster, Tobias; Saha, Koushik; Roy, Dipak Kumar; Dewhurst, Rian D.; Braunschweig, Holger; Chemical communications (Cambridge, England) 62 (2026) 5032–5036; doi:10.1039/d5cc05783c

data_7135346
_publ_section_title
;
 Ring expansion of an antiaromatic beryllole: synthesis of novel five-,
 seven- and nine-membered beryllacycles.
;
_journal_issue                   17
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              5032
_journal_page_last               5036
_journal_paper_doi               10.1039/d5cc05783c
_journal_volume                  62
_journal_year                    2026
_chemical_formula_moiety         'C54 H60 B2 Be N2'
_chemical_formula_sum            'C54 H60 B2 Be N2'
_chemical_formula_weight         767.67
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           'CIF-fill 1.2x (K.Radacki, 2005-21)'
_audit_update_record
;
2025-10-09 deposited with the CCDC.	2026-02-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.5530(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.23120(10)
_cell_length_b                   12.89530(10)
_cell_length_c                   16.69960(10)
_cell_measurement_reflns_used    62865
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      79.5230
_cell_measurement_theta_min      2.6240
_cell_volume                     4342.97(5)
_computing_cell_refinement       'CrysAlisPro 1.171.41.111a (Rigaku OD, 2021)'
_computing_data_collection       'BIS 2011.8 / APEX2 ver. 2014.9 (Bruker AXS)'
_computing_data_reduction        'CrysAlisPro 1.171.41.111a (Rigaku OD, 2021)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 HPA
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'HyPix 6000'
_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   -120.00 -69.00   0.50    0.10    --  -47.96-127.00  49.00  102
   2  \w   -104.00 -19.00   0.50    0.10    --  -47.96 143.00 -64.00  170
   3  \w    -93.00 -11.00   0.50    0.10    --  -47.96 127.00 125.00  164
   4  \w   -120.00 -58.00   0.50    0.10    --  -47.96-143.00-119.00  124
   5  \w     33.00  97.00   0.50    0.10    --   47.96-127.00  49.00  128
   6  \w     41.00 106.00   0.50    0.10    --   47.96-143.00-119.00  130
   7  \w   -159.00 -58.00   0.50    0.38    --  -91.75-143.00-119.00  202
   8  \w   -163.00 -69.00   0.50    0.38    --  -91.75-127.00  49.00  188
   9  \w     80.00 176.00   0.50    0.38    --  113.25 143.00 -64.00  192
  10  \w     42.00 118.00   0.50    0.38    --  113.25-127.00  49.00  152
  11  \w     42.00 130.00   0.50    0.38    --  113.25-143.00-119.00  176
  12  \w     91.00 178.00   0.50    0.38    --  113.25 127.00 125.00  174
  13  \w    -26.00   1.00   0.50    0.10    --   14.00 111.00   5.34   54
  14  \w    -56.00 -30.00   0.50    0.10    --   18.00 165.00 156.37   52
  15  \w    -12.00  21.00   0.50    0.10    --   22.00 101.00 -55.18   66
  16  \w    -10.00  32.00   0.50    0.10    --   22.00  96.00 137.28   84
  17  \w      4.00  37.00   0.50    0.10    --   34.00  93.00-146.74   66
  18  \w     13.00  46.00   0.50    0.10    --   42.00  90.00  14.42   66
  19  \w     20.00  46.00   0.50    0.10    --   46.00  85.00 109.88   52
  20  \w     19.00  46.00   0.50    0.10    --   46.00  87.00 171.59   54
  21  \w     18.00  46.00   0.50    0.10    --   46.00  88.00-121.05   56
  22  \w     16.00  44.00   0.50    0.10    --   46.00  92.00  63.85   56
  23  \w   -122.00 -35.00   0.50    0.10    --  -47.96 -19.00 -60.00  174
  24  \w    -63.00 -29.00   0.50    0.10    --  -54.00 -83.00  17.37   68
  25  \w    -87.00 -28.00   0.50    0.10    --  -54.00 -83.00 149.85  118
  26  \w    -71.00 -31.00   0.50    0.10    --  -54.00 -81.00 179.57   80
  27  \w    -55.00 -29.00   0.50    0.10    --  -54.00 -81.00 -37.50   52
  28  \w     30.00  80.00   0.50    0.10    --   54.00  79.00  86.57  100
  29  \w    -58.00 -33.00   0.50    0.10    --  -58.00 -82.00  87.63   50
  30  \w   -121.00 -95.00   0.50    0.10    --  -58.00 -82.00  87.63   52
  31  \w     37.00  70.00   0.50    0.10    --   58.00  73.00 -78.11   66
  32  \w     36.00  62.00   0.50    0.10    --   58.00  76.00-117.42   52
  33  \w    -62.00 -36.00   0.50    0.10    --  -62.00 -83.00 -50.23   52
  34  \w    -80.00 -40.00   0.50    0.10    --  -62.00 -83.00 -76.86   80
  35  \w    -64.00 -39.00   0.50    0.10    --  -62.00 -83.00  48.93   50
  36  \w    -63.00 -37.00   0.50    0.10    --  -62.00 -81.00 114.35   52
  37  \w     41.00  67.00   0.50    0.10    --   62.00  73.00  11.69   52
  38  \w    -69.00 -44.00   0.50    0.10    --  -66.00 -74.00 129.24   50
  39  \w    -69.00 -44.00   0.50    0.10    --  -66.00 -75.00 166.07   50
  40  \w     43.00  74.00   0.50    0.10    --   66.00  77.00 166.99   62
  41  \w     81.00 127.00   0.50    0.10    --   66.00  77.00 166.99   92
  42  \w     47.00  80.00   0.50    0.10    --   70.00  77.00-132.28   66
  43  \w    -84.00 -51.00   0.50    0.38    --  -70.00 -67.00-103.20   66
  44  \w    -71.00 -45.00   0.50    0.38    --  -70.00 -83.00-105.72   52
  45  \w     47.00  72.00   0.50    0.10    --   70.00  78.00  14.60   50
  46  \w    -87.00 -55.00   0.50    0.38    --  -74.00 -73.00 171.40   64
  47  \w    -75.00 -49.00   0.50    0.38    --  -74.00 -83.00 113.82   52
  48  \w    -85.00 -52.00   0.50    0.38    --  -74.00 -76.00 -60.72   66
  49  \w    -76.00 -51.00   0.50    0.38    --  -74.00 -76.00 -31.86   50
  50  \w   -147.00 -98.00   0.50    0.38    --  -78.00 -82.00 143.86   98
  51  \w    -84.00 -52.00   0.50    0.38    --  -78.00 -83.00  49.89   64
  52  \w    -87.00 -55.00   0.50    0.38    --  -78.00 -76.00-135.40   64
  53  \w    -82.00 -56.00   0.50    0.38    --  -78.00 -74.00  78.09   52
  54  \w    -81.00 -55.00   0.50    0.38    --  -78.00 -76.00-150.25   52
  55  \w    -90.00 -57.00   0.50    0.38    --  -78.00 -75.00  64.79   66
  56  \w    -79.00 -53.00   0.50    0.38    --  -78.00 -81.00 168.64   52
  57  \w    -92.00 -53.00   0.50    0.38    --  -78.00 -82.00 143.86   78
  58  \w    -90.00 -56.00   0.50    0.38    --  -82.00 -83.00  71.17   68
  59  \w    -90.00 -64.00   0.50    0.38    --  -82.00 -67.00 -72.85   52
  60  \w    -86.00 -60.00   0.50    0.38    --  -82.00 -74.00   5.65   52
  61  \w    -92.00 -60.00   0.50    0.38    --  -82.00 -75.00 -95.29   64
  62  \w    -93.00 -64.00   0.50    0.38    --  -86.00 -75.00 124.48   58
  63  \w    -89.00 -63.00   0.50    0.38    --  -86.00 -77.00 -24.50   52
  64  \w   -102.00 -67.00   0.50    0.38    --  -90.00 -77.00  52.74   70
  65  \w    -94.00 -68.00   0.50    0.38    --  -91.75 -80.00  -5.27   52
  66  \w   -120.00 -69.00   0.50    0.38    --  -91.75 -77.00-150.00  102
  67  \w   -106.00 -69.00   0.50    0.38    --  -91.75 -77.00  90.00   74
  68  \w    -94.00 -68.00   0.50    0.38    --  -91.75 -79.00 -32.72   52
  69  \w    -96.00 -68.00   0.50    0.38    --  -91.75 -81.00 171.56   56
  70  \w   -159.00-101.00   0.50    0.38    --  -91.75 -81.00 171.56  116
  71  \w   -128.00 -72.00   0.50    0.38    --  -91.75 -72.00  62.15  112
  72  \w   -106.00 -71.00   0.50    0.38    --  -91.75 -73.00 -87.66   70
  73  \w   -112.00 -70.00   0.50    0.38    --  -91.75 -75.00  33.87   84
  74  \w   -115.00 -70.00   0.50    0.38    --  -91.75 -75.00 -71.53   90
  75  \w   -101.00 -67.00   0.50    0.38    --  -91.75 -81.00 115.78   68
  76  \w   -163.00 -67.00   0.50    0.38    --  -91.75 -82.00 151.95  192
  77  \w    -86.00 -61.00   0.50    0.38    --  -91.75 143.00 -64.00   50
  78  \w    -80.00 -55.00   0.50    0.38    --  -91.75 127.00 125.00   50
  79  \w   -110.00 -68.00   0.50    0.38    --  -91.75 -79.00-114.27   84
  80  \w   -163.00 -66.00   0.50    0.38    --  -91.75 -83.00 -95.81  194
  81  \w    -94.00 -68.00   0.50    0.38    --  -91.75 -78.00   6.79   52
  82  \w     70.00  98.00   0.50    0.38    --   94.00  79.00 177.17   56
  83  \w    138.00 175.00   0.50    0.38    --  102.00  80.00 -67.73   74
  84  \w     78.00 134.00   0.50    0.38    --  102.00  80.00 -67.73  112
  85  \w    145.00 174.00   0.50    0.38    --  102.00  80.00-168.54   58
  86  \w    118.00 143.00   0.50    0.38    --  102.00  80.00-168.54   50
  87  \w     78.00 105.00   0.50    0.38    --  102.00  80.00-168.54   54
  88  \w     98.00 157.00   0.50    0.38    --  113.25  61.00 120.00  118
  89  \w     97.00 160.00   0.50    0.38    --  113.25  61.00   0.00  126
  90  \w     42.00  68.00   0.50    0.38    --  113.25 -61.00   0.00   52
  91  \w     76.00 106.00   0.50    0.38    --  113.25 -77.00-150.00   60
  92  \w     43.00  68.00   0.50    0.38    --  113.25 -77.00-150.00   50
  93  \w    101.00 176.00   0.50    0.38    --  113.25  61.00-120.00  150
  94  \w     96.00 173.00   0.50    0.38    --  113.25  77.00 150.00  154
  95  \w     43.00  89.00   0.50    0.38    --  113.25 -77.00 150.00   92
  96  \w     42.00 112.00   0.50    0.38    --  113.25-125.00 -90.00  140
  97  \w     45.00  87.00   0.50    0.38    --  113.25 -77.00  90.00   84
  98  \w    105.00 149.00   0.50    0.38    --  113.25  77.00 -90.00   88
  99  \w     42.00  69.00   0.50    0.38    --  113.25 -61.00-120.00   54
 100  \w    133.00 177.00   0.50    0.38    --  113.25  77.00 120.00   88
 101  \w     91.00 117.00   0.50    0.38    --  113.25  77.00 120.00   52
 102  \w     72.00 117.00   0.50    0.38    --  113.25-125.00  90.00   90
 103  \w     92.00 177.00   0.50    0.38    --  113.25  77.00 -60.00  170
 104  \w     43.00  69.00   0.50    0.38    --  113.25-125.00  90.00   52
 105  \w     93.00 175.00   0.50    0.38    --  113.25  77.00-150.00  164
 106  \w    129.00 177.00   0.50    0.38    --  113.25  77.00  90.00   96
 107  \w     92.00 172.00   0.50    0.38    --  113.25  77.00   0.00  160
 108  \w     98.00 150.00   0.50    0.38    --  113.25  61.00  90.00  104
 109  \w    100.00 174.00   0.50    0.38    --  113.25  61.00 -90.00  148
 110  \w     93.00 147.00   0.50    0.38    --  113.25  77.00  30.00  108
 111  \w     42.00 117.00   0.50    0.38    --  113.25-125.00-120.00  150
 112  \w     93.00 122.00   0.50    0.38    --  113.25  77.00  60.00   58
 113  \w     97.00 175.00   0.50    0.38    --  113.25  61.00  60.00  156
 114  \w     94.00 122.00   0.50    0.38    --  113.25  77.00  90.00   56
 115  \w     78.00 113.00   0.50    0.38    --  113.25-125.00   0.00   70
 116  \w     74.00  99.00   0.50    0.38    --  113.25 -94.00 -30.00   50
 117  \w     42.00  68.00   0.50    0.38    --  113.25 -94.00 -30.00   52
 118  \w     42.00  75.00   0.50    0.38    --  113.25-125.00   0.00   66
 119  \w    100.00 169.00   0.50    0.38    --  113.25  61.00-180.00  138
 120  \w     91.00 170.00   0.50    0.38    --  113.25  77.00 -30.00  158
 121  \w     98.00 176.00   0.50    0.38    --  113.25  61.00  30.00  156
 122  \w     43.00 116.00   0.50    0.38    --  113.25-125.00-180.00  146
 123  \w     63.00 109.00   0.50    0.38    --  113.25 -94.00  60.00   92
 124  \w    102.00 145.00   0.50    0.38    --  113.25  61.00-150.00   86
 125  \w     44.00  70.00   0.50    0.38    --  113.25 -61.00  30.00   52
 126  \w    100.00 156.00   0.50    0.38    --  113.25  61.00 150.00  112
 127  \w     75.00 104.00   0.50    0.38    --  113.25 -94.00  90.00   58
 128  \w     47.00  72.00   0.50    0.38    --  113.25 -94.00  90.00   50
 129  \w     43.00 116.00   0.50    0.38    --  113.25-125.00 -30.00  146
 130  \w     91.00 146.00   0.50    0.38    --  113.25  77.00-120.00  110
 131  \w     92.00 117.00   0.50    0.38    --  113.25-125.00 -60.00   50
 132  \w     45.00 101.00   0.50    0.38    --  113.25 -77.00 -30.00  112
 133  \w     42.00  76.00   0.50    0.38    --  113.25-125.00 -60.00   68
 134  \w     97.00 153.00   0.50    0.38    --  113.25  61.00 -30.00  112
 135  \w     44.00  71.00   0.50    0.38    --  113.25 -61.00  90.00   54

;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy-S'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  'multi-layer mirror'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_unetI/netI     0.0105
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            85778
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        72.000
_diffrn_reflns_theta_max         72.127
_diffrn_reflns_theta_min         4.069
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet X-ray Source'
_exptl_absorpt_coefficient_mu    0.492
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.545
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.111a (Rigaku Oxford Diffraction, 2021) 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            colourless
_exptl_crystal_density_diffrn    1.174
_exptl_crystal_description       block
_exptl_crystal_F_000             1648
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.146
_exptl_crystal_size_min          0.124
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     287
_refine_ls_number_reflns         4274
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0404
_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^)+(0.0509P)^2^+3.8707P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1044
_refine_ls_wR_factor_ref         0.1052
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4117
_reflns_number_total             4274
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc05783c2.cif
_cod_data_source_block           ToBi161_ToTr_a
_cod_depositor_comments
'Adding full bibliography for 7135342--7135346.cif.'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7135346
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.921
_shelx_estimated_absorpt_t_max   0.943
_shelx_res_checksum              35380
_shelx_hkl_checksum              3318