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_7714629
_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         'C80 H58 B4 K2 N2, 7(C6 H6)'
_chemical_formula_sum            'C122 H100 B4 K2 N2'
_chemical_formula_weight         1715.48
_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             2023-02-27
_audit_creation_method           'CIF-fill 1.3q (K.Radacki, 2005-22)'
_audit_update_record
;
2023-10-13 deposited with the CCDC.	2023-12-06 downloaded from the CCDC.
;
_cell_angle_alpha                86.734(2)
_cell_angle_beta                 84.599(2)
_cell_angle_gamma                82.053(2)
_cell_formula_units_Z            1
_cell_length_a                   10.0169(2)
_cell_length_b                   14.8735(3)
_cell_length_c                   16.2360(3)
_cell_measurement_reflns_used    18689
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.0490
_cell_measurement_theta_min      2.9850
_cell_volume                     2382.70(8)
_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-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      100(2)
_diffrn_detector                 HPA
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'HyPix Arc150'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_details
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  \w    -98.00 -34.00   0.50    0.70    --  -79.50 121.00-120.30  128
  2  \w    -97.00 -36.00   0.50    0.70    --  -79.50 115.00 -21.49  122
  3  \w    -97.00 -35.00   0.50    0.70    --  -79.50 116.00  85.75  124
  4  \w    -99.00 -33.00   0.50    0.70    --  -78.00 121.00 110.73  132
  5  \w    -97.00 -36.00   0.50    0.70    --  -79.50 114.00 155.64  122
  6  \w    -62.00 -36.00   0.50    0.70    --  -79.50 126.00 165.93   52
  7  \w    -97.00 -44.00   0.50    0.70    --  -79.50 114.00  31.27  106
  8  \w    -83.00 -39.00   0.50    0.70    --  -79.50  93.00  43.46   88
  9  \w    -85.00 -39.00   0.50    0.70    --  -79.50  97.00 -47.77   92
 10  \w    -89.00 -37.00   0.50    0.70    --  -79.50 102.00-144.84  104
 11  \w    -97.00 -36.00   0.50    0.70    --  -79.50 114.00 -81.33  122
 12  \w    -97.00 -36.00   0.50    0.70    --  -79.50 114.00 -31.61  122
 13  \w     66.00  96.00   0.50    0.70    --   50.00  52.00 -17.26   60
 14  \w     62.00  92.00   0.50    0.70    --   46.00  52.00  36.34   60
 15  \w     58.00  88.00   0.50    0.70    --   42.00  52.00  94.09   60
 16  \w     95.00 120.00   0.50    0.70    --   83.50 128.00 119.20   50
 17  \w     92.00 119.00   0.50    0.70    --   83.50 137.00  14.20   54
 18  \w    102.00 128.00   0.50    0.70    --   83.50 119.00 -24.19   52
 19  \w    101.00 128.00   0.50    0.70    --   83.50 124.00-153.13   54
 20  \w    100.00 126.00   0.50    0.70    --   83.50 121.00-131.80   52
 21  \w    101.00 127.00   0.50    0.70    --   83.50  60.00 -55.70   52
 22  \w    100.00 126.00   0.50    0.70    --   83.50  52.00-104.06   52
 23  \w     98.00 127.00   0.50    0.70    --   83.50  59.00-178.35   58
 24  \w     99.00 128.00   0.50    0.70    --   80.38  15.00-120.00   58
 25  \w     97.00 124.00   0.50    0.70    --   80.38  15.00 -90.00   54
 26  \w     99.00 124.00   0.50    0.70    --   83.50  53.00 139.23   50
 27  \w     64.00 131.00   0.50    0.70    --   83.50  14.00 175.20  134
 28  \w     40.00  65.00   0.50    0.70    --   80.38 -95.00 -30.00   50
 29  \w     46.00  81.00   0.50    0.70    --   83.50-119.00-144.58   70
 30  \w     70.00  96.00   0.50    0.70    --   83.50-116.00-125.38   52
 31  \w     62.00  88.00   0.50    0.70    --   80.38-112.00-180.00   52
 32  \w     45.00  98.00   0.50    0.70    --   83.50-119.00 -44.14  106
 33  \w     48.00  92.00   0.50    0.70    --   80.38-112.00   0.00   88
 34  \w     39.00 102.00   0.50    0.70    --   83.50-137.00  58.15  126
 35  \w     57.00  88.00   0.50    0.70    --   83.50-109.00  49.54   62
 36  \w     46.00  97.00   0.50    0.70    --   83.50-115.00 128.42  102
 37  \w     62.00  88.00   0.50    0.70    --   80.38-112.00 150.00   52
 38  \w     44.00  92.00   0.50    0.70    --   83.50-103.00  63.66   96
 39  \w     49.00  75.00   0.50    0.70    --   80.38 -95.00 120.00   52
 40  \w     44.00  93.00   0.50    0.70    --   83.50-105.00-128.20   98
 41  \w     40.00  65.00   0.50    0.70    --   80.38 -95.00-180.00   50
 42  \w     43.00  92.00   0.50    0.70    --   83.50-102.00 -97.07   98
 43  \w     45.00  71.00   0.50    0.70    --   80.38 -95.00 -90.00   52
 44  \w     53.00  79.00   0.50    0.70    --   80.38 -95.00 -60.00   52
 45  \w     40.00  66.00   0.50    0.70    --   80.38 -95.00   0.00   52
 46  \w   -128.00 -94.00   0.50    0.70    --  -79.50 -41.00 -36.01   68
 47  \w   -118.00 -88.00   0.50    0.70    --  -74.00 -59.00  52.10   60
 48  \w   -121.00 -95.00   0.50    0.70    --  -79.50 -65.00  94.04   52
 49  \w   -122.00 -97.00   0.50    0.70    --  -79.50 -64.00 110.77   50
 50  \w   -122.00 -95.00   0.50    0.70    --  -79.50 -65.00 136.32   54
 51  \w   -114.00 -85.00   0.50    0.70    --  -70.00 -59.00 168.42   58
 52  \w   -126.00 -95.00   0.50    0.70    --  -79.50 -52.00  38.71   62
 53  \w   -126.00 -96.00   0.50    0.70    --  -79.50 -49.00  21.83   60
 54  \w   -112.00 -81.00   0.50    0.70    --  -66.00 -52.00 -85.69   62
 55  \w   -127.00 -95.00   0.50    0.70    --  -79.50 -44.00  -4.42   64
 56  \w   -109.00 -78.00   0.50    0.70    --  -62.00 -47.00 -68.17   62
 57  \w   -109.00 -78.00   0.50    0.70    --  -62.00 -47.00-131.71   62
 58  \w   -122.00 -89.00   0.50    0.70    --  -74.00 -44.00-154.81   66
 59  \w   -126.00 -95.00   0.50    0.70    --  -79.50 -51.00-155.80   62
 60  \w   -121.00 -86.00   0.50    0.70    --  -79.50-134.00-145.28   70
 61  \w   -125.00 -88.00   0.50    0.70    --  -79.50-130.00 -80.66   74
 62  \w   -124.00 -87.00   0.50    0.70    --  -79.50-133.00 -59.74   74
 63  \w   -124.00 -87.00   0.50    0.70    --  -79.50-133.00  15.41   74
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy-R'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
;
 CrysAlisPro convention (1999,Acta A55,543-557)
;
_diffrn_orient_matrix_UB_11      -0.1032482000
_diffrn_orient_matrix_UB_12      -0.0399999000
_diffrn_orient_matrix_UB_13      -0.0468969000
_diffrn_orient_matrix_UB_21      -0.0386577000
_diffrn_orient_matrix_UB_22      0.0936052000
_diffrn_orient_matrix_UB_23      -0.0433076000
_diffrn_orient_matrix_UB_31      0.1102013000
_diffrn_orient_matrix_UB_32      -0.0244390000
_diffrn_orient_matrix_UB_33      -0.0709008000
_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  0.0507
_diffrn_reflns_av_unetI/netI     0.0373
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            49032
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.789
_diffrn_reflns_theta_min         2.736
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet-R X-ray Source'
_exptl_absorpt_coefficient_mu    1.274
_exptl_absorpt_correction_T_max  0.880
_exptl_absorpt_correction_T_min  0.424
_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            red
_exptl_crystal_density_diffrn    1.196
_exptl_crystal_description       plate
_exptl_crystal_F_000             904
_exptl_crystal_preparation
;
 Crystals were grown from saturated solution of benzene at 23 \%C. 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          0.090
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.394
_refine_diff_density_min         -0.553
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     617
_refine_ls_number_reflns         9623
_refine_ls_number_restraints     180
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0499
_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^)+(0.0782P)^2^+0.6178P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1338
_refine_ls_wR_factor_ref         0.1418
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7763
_reflns_number_total             9623
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3dt03826b2.cif
_cod_data_source_block           AnLa134_AnLa_a_sq
_cod_depositor_comments
'Adding full bibliography for 7714624--7714631.cif.'
_cod_database_code               7714629
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.898
_shelx_estimated_absorpt_t_max   0.976
_shelx_res_checksum              43204