Synthesis, reduction and C-H activation chemistry of azaborinines with redox-active organoboryl substituents.
Lamprecht, Anna; Arrowsmith, Merle; Dietz, Maximilian; Fuchs, Sonja; Rempel, Anna; Härterich, Marcel; Braunschweig, Holger; Dalton transactions (Cambridge, England : 2003) 53 (2024) 1004–1013; doi:10.1039/d3dt03826b

data_7714626
_publ_section_title
;
 Synthesis, reduction and C-H activation chemistry of azaborinines with
 redox-active organoboryl substituents.
;
_journal_issue                   3
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              1004
_journal_page_last               1013
_journal_paper_doi               10.1039/d3dt03826b
_journal_volume                  53
_journal_year                    2024
_chemical_formula_moiety         'C46 H33 B3 Br N, 1.5(C6 H6)'
_chemical_formula_sum            'C55 H42 B3 Br N'
_chemical_formula_weight         829.23
_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             2022-08-23
_audit_creation_method           'CIF-fill 1.3i (K.Radacki, 2005-22)'
_audit_update_record
;
2023-10-13 deposited with the CCDC.	2023-12-06 downloaded from the CCDC.
;
_cell_angle_alpha                99.0550(10)
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_cell_angle_gamma                117.208(2)
_cell_formula_units_Z            2
_cell_length_a                   12.4227(2)
_cell_length_b                   12.5117(2)
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_cell_measurement_temperature    293(2)
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_computing_cell_refinement       'CrysAlisPro 1.171.40.81a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.81a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.81a (Rigaku OD, 2020)'
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 HPA
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'HyPix 6000'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  \w     91.00 178.00   0.50    0.09    --  107.75  61.00  30.00  174
  2  \w     88.00 165.00   0.50    0.09    --  107.75  71.00  40.28  154
  3  \w     91.00 178.00   0.50    0.09    --  107.75  61.00 150.00  174
  4  \w     91.00 127.00   0.50    0.09    --  107.75  61.00 -60.00   72
  5  \w    136.00 169.00   0.50    0.09    --  107.75  61.00 -60.00   66
  6  \w     89.00 178.00   0.50    0.09    --  107.75  71.00-106.44  178
  7  \w     91.00 178.00   0.50    0.09    --  107.75  61.00-180.00  174
  8  \w     94.00 178.00   0.50    0.09    --  107.75  15.00-120.00  168
  9  \w    122.00 153.00   0.50    0.09    --  107.75  30.00 -60.00   62
 10  \w     94.00 178.00   0.50    0.09    --  107.75  15.00 -30.00  168
 11  \w    126.00 177.00   0.50    0.09    --  107.75  30.00  90.00  102
 12  \w    -26.00  28.00   0.50    0.05    --  -47.70  19.00 -60.00  108
 13  \w    -51.00 -14.00   0.50    0.09    --  -86.25  45.00 150.00   74
 14  \w    -42.00  26.00   0.50    0.05    --  -47.70  37.00  60.00  136
 15  \w    -51.00 -14.00   0.50    0.09    --  -86.25  45.00-120.00   74
 16  \w    -42.00  26.00   0.50    0.05    --  -47.70  37.00-180.00  136
 17  \w     86.00 129.00   0.50    0.09    --  107.75-149.00  44.95   86
 18  \w     83.00 110.00   0.50    0.09    --  107.75-125.00  90.00   54
 19  \w     35.00 112.00   0.50    0.09    --  107.75-125.00-120.00  154
 20  \w     87.00 112.00   0.50    0.09    --  107.75-125.00-150.00   50
 21  \w     37.00  67.00   0.50    0.09    --  107.75-125.00-180.00   60
 22  \w     45.00  71.00   0.50    0.09    --  107.75-125.00-150.00   52
 23  \w     70.00 102.00   0.50    0.09    --  107.75-125.00-180.00   64
 24  \w     35.00 112.00   0.50    0.09    --  107.75-125.00 -90.00  154
 25  \w     35.00 108.00   0.50    0.09    --  107.75-113.00 -39.78  146
 26  \w     36.00  65.00   0.50    0.09    --  107.75-106.00  22.21   58
 27  \w     82.00 107.00   0.50    0.09    --  107.75-106.00  22.21   50
 28  \w     35.00 106.00   0.50    0.09    --  107.75 -94.00   0.00  142
 29  \w      4.00  82.00   0.50    0.05    --   47.70-101.00 114.00  156
 30  \w     -1.00  81.00   0.50    0.05    --   47.70 -99.00   0.00  164
 31  \w     35.00 106.00   0.50    0.09    --  107.75-101.00 114.00  142
 32  \w     39.00 109.00   0.50    0.09    --  107.75-125.00 150.00  140
 33  \w     63.00  89.00   0.50    0.09    --  107.75 -94.00 150.00   52
 34  \w     36.00  97.00   0.50    0.09    --  107.75 -94.00  90.00  122
 35  \w     43.00  69.00   0.50    0.09    --  107.75 -94.00 -30.00   52
 36  \w     54.00  81.00   0.50    0.09    --  107.75 -94.00 -60.00   54
 37  \w     69.00 105.00   0.50    0.09    --  107.75 -94.00 -90.00   72
 38  \w     38.00 106.00   0.50    0.09    --  107.75 -94.00-180.00  136
 39  \w     36.00 105.00   0.50    0.09    --  107.75 -77.00-150.00  138
 40  \w     35.00  70.00   0.50    0.09    --  107.75 -61.00-120.00   70
 41  \w    -27.00  26.00   0.50    0.05    --   47.70 -19.00-150.00  106
 42  \w     45.00  71.00   0.50    0.09    --  107.75 -61.00 -30.00   52
 43  \w     35.00 106.00   0.50    0.09    --  107.75 -77.00 -30.00  142
 44  \w     35.00  71.00   0.50    0.09    --  107.75 -61.00 120.00   72
 45  \w    107.00 178.00   0.50    0.09    --  107.75 101.00-141.00  142
 46  \w     95.00 178.00   0.50    0.09    --  107.75 125.00-180.00  166
 47  \w     95.00 178.00   0.50    0.09    --  107.75 125.00   0.00  166
 48  \w    120.00 151.00   0.50    0.09    --  107.75 125.00 150.00   62
 49  \w   -159.00 -67.00   0.50    0.09    --  -86.25 -67.00 179.97  184
 50  \w   -159.00 -85.00   0.50    0.09    --  -86.25-101.00 114.00  148
 51  \w   -119.00 -73.00   0.50    0.05    --  -47.70-125.00  90.00   92
 52  \w   -119.00 -73.00   0.50    0.05    --  -47.70-125.00-150.00   92
 53  \w    -81.00 -13.00   0.50    0.09    --  -86.25 101.00-141.00  136
 54  \w    -81.00  18.00   0.50    0.05    --  -47.70 101.00-141.00  198
;
_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      0.0209953000
_diffrn_orient_matrix_UB_12      -0.0310581000
_diffrn_orient_matrix_UB_13      -0.0930166000
_diffrn_orient_matrix_UB_21      0.0252844000
_diffrn_orient_matrix_UB_22      -0.1023379000
_diffrn_orient_matrix_UB_23      0.0236488000
_diffrn_orient_matrix_UB_31      -0.1383196000
_diffrn_orient_matrix_UB_32      -0.0937709000
_diffrn_orient_matrix_UB_33      -0.0299496000
_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  0.0423
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            42013
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        70.063
_diffrn_reflns_theta_max         70.063
_diffrn_reflns_theta_min         2.884
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet X-ray Source'
_exptl_absorpt_coefficient_mu    1.612
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.138
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
 CrysAlisPro 1.171.40.81a (Rigaku Oxford Diffraction, 2020) 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    1.300
_exptl_crystal_description       block
_exptl_crystal_F_000             858
_exptl_crystal_preparation
;
 Crystalls were grown from saturated solution. 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_size_max          0.464
_exptl_crystal_size_mid          0.365
_exptl_crystal_size_min          0.253
_refine_diff_density_max         0.795
_refine_diff_density_min         -0.626
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     599
_refine_ls_number_reflns         8037
_refine_ls_number_restraints     252
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0449
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0727P)^2^+2.1971P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1281
_refine_ls_wR_factor_ref         0.1297
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7521
_reflns_number_total             8037
_reflns_threshold_expression     'I > 2\s(I)'
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_cod_data_source_block           AnRe189_ref_a
_cod_depositor_comments
'Adding full bibliography for 7714624--7714631.cif.'
_cod_original_cell_volume        2118.10(6)
_cod_database_code               7714626
_shelx_shelxl_version_number     2018/3
_shelx_res_checksum              1828