Regio- and Chemoselective Diboration of Allenes with Unsymmetrical Diboron: Formation of Vinyl and Allyl Boronic Acid Derivatives
Guo, Xi; Nelson, Amanda K.; Slebodnick, Carla; Santos, Webster L.; ACS Catalysis  (2015) 2172–; doi:10.1021/acscatal.5b00387

data_4512822
_publ_section_title
;
 Regio- and Chemoselective Diboration of Allenes with Unsymmetrical
 Diboron: Formation of Vinyl and Allyl Boronic Acid Derivatives
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              2172
_journal_paper_doi               10.1021/acscatal.5b00387
_journal_year                    2015
_chemical_formula_moiety         'C31 H32 B2 N2 O2'
_chemical_formula_sum            'C31 H32 B2 N2 O2'
_chemical_formula_weight         486.21
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2012-07-06
_audit_creation_method
;
  Olex2 1.2
  (compiled May  9 2012 12:37:22, GUI svn.r4230)
;
_cell_angle_alpha                85.896(3)
_cell_angle_beta                 77.575(3)
_cell_angle_gamma                73.572(3)
_cell_formula_units_Z            2
_cell_length_a                   9.5673(4)
_cell_length_b                   12.0514(4)
_cell_length_c                   12.4802(5)
_cell_measurement_reflns_used    11048
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      32.3742
_cell_measurement_theta_min      3.5182
_cell_volume                     1347.80(9)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 16.0122
_diffrn_detector_type            'Oxford Diffraction Eos CCD'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.933
_diffrn_measurement_details
;
  1 omega  -36.00  -10.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -29.3753  -77.0000   60.0000 26

  2 omega  -37.00   44.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -29.3753   38.0000 -180.0000 81

  3 omega  -95.00   -2.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -29.3753  -77.0000  -60.0000 93

  4 omega  -67.00  -26.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -29.3753   85.0000  177.0000 41

  5 omega    7.00   39.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -29.3753   85.0000  177.0000 32

  6 omega  -57.00   39.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -29.3753   77.0000   60.0000 96

  7 omega  -59.00   -1.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -29.3753  -77.0000 -150.0000 58

  8 omega  -94.00  -68.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -29.3753  -77.0000   60.0000 26

  9 omega -102.00    4.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -29.3753  -77.0000   90.0000 106

 10 omega -100.00   -6.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -29.3753  -57.0000 -150.0000 94

 11 omega -109.00  -35.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -29.3753 -178.0000  150.0000 74

 12 omega -100.00   -6.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -29.3753  -57.0000  -30.0000 94

 13 omega -112.00  -32.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -29.3753  178.0000  -90.0000 80

 14 omega  -50.00   44.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -29.3753   38.0000    0.0000 94

 15 omega -100.00  -17.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -29.3753  -57.0000  120.0000 83
;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Oxford Diffraction Gemini Ultra'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_orient_matrix_UB_11      -0.0549469000
_diffrn_orient_matrix_UB_12      0.0493902000
_diffrn_orient_matrix_UB_13      0.0243427000
_diffrn_orient_matrix_UB_21      -0.0353693000
_diffrn_orient_matrix_UB_22      0.0058934000
_diffrn_orient_matrix_UB_23      -0.0453600000
_diffrn_orient_matrix_UB_31      -0.0443048000
_diffrn_orient_matrix_UB_32      -0.0359388000
_diffrn_orient_matrix_UB_33      0.0271528000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            34637
_diffrn_reflns_theta_full        31.00
_diffrn_reflns_theta_max         32.45
_diffrn_reflns_theta_min         3.53
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_target            Mo
_diffrn_source_type              'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95353
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.198
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             516
_exptl_crystal_size_max          0.3523
_exptl_crystal_size_mid          0.2879
_exptl_crystal_size_min          0.2188
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.047
_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     338
_refine_ls_number_reflns         9057
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0661
_refine_ls_R_factor_gt           0.0485
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0621P)^2^+0.3544P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1204
_refine_ls_wR_factor_ref         0.1344
_reflns_number_gt                6983
_reflns_number_total             9057
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cs5b00387_si_003.cif
_cod_data_source_block           cs1891
_cod_original_cell_volume        1347.79(9)
_cod_database_code               4512822
_chemical_oxdiff_formula         'C31 H32 B2 N2 O2'
_chemical_oxdiff_usercomment     'Amanda Nelson/Webster Santos (BDA 2.1a-16)'