Hydrazone as the directing Group for Ir-Catalyzed Arene Diborylations and Sequential Functionalizations
Abel Ros; Rocío López-Rodríguez; Beatriz Estepa; Eleuterio Álvarez; Rosario Fernández; José M. Lassaletta; Journal of the American Chemical Society 134 (2012) 4573–4576; doi:10.1021/ja300308c

data_4117681
_publ_contact_author_address
;
  Dr. Jos\'e M. Lassaletta
     Instituto de Investigaciones Qu\'imicas, C.S.I.C-Universidad de Sevilla,
     Avd. Am\'erico Vespucio, 49., Isla de la Cartuja, E-41092 Sevilla,  Spain  
;
_publ_contact_author_email       jmlassa@iiq.csic.es
_publ_contact_author_fax         '+34 954 460565'
_publ_contact_author_name        'Dr. Jos\'e M. Lassaletta'
_publ_contact_author_phone       '+34 954 489563'
_publ_section_title
;
 Hydrazone as the directing Group for Ir-Catalyzed Arene Diborylations and
 Sequential Functionalizations
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4573
_journal_page_last               4576
_journal_paper_doi               10.1021/ja300308c
_journal_volume                  134
_journal_year                    2012
_chemical_formula_moiety         'C16 H25 B N2 O3'
_chemical_formula_sum            'C16 H25 B N2 O3'
_chemical_formula_weight         304.19
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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_method           SHELXL-97
_cell_angle_alpha                78.2360(10)
_cell_angle_beta                 85.0880(10)
_cell_angle_gamma                68.2820(9)
_cell_formula_units_Z            2
_cell_length_a                   9.2419(5)
_cell_length_b                   9.6877(6)
_cell_length_c                   10.6092(6)
_cell_measurement_reflns_used    9895
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      30.50
_cell_measurement_theta_min      2.64
_cell_volume                     863.86(9)
_computing_cell_refinement       'APEX2 Software Suite (Bruker, 2007)'
_computing_data_collection       'APEX2 Software Suite (Bruker, 2007)'
_computing_data_reduction        'APEX2 Software Suite (Bruker, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL and publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2002 (Burla et al., 2003)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 8.26
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type
;
 Bruker-Nonius X8kappa APEX II CCD area detector
;
_diffrn_measurement_method       'phi and omega scans with narrow frames'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_av_sigmaI/netI    0.0142
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            29388
_diffrn_reflns_theta_full        30.57
_diffrn_reflns_theta_max         30.57
_diffrn_reflns_theta_min         1.96
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.9651
_exptl_absorpt_correction_T_min  0.9564
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
program SADABS, Bruker (2001).
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.169
_exptl_crystal_description       block
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.45
_refine_diff_density_max         0.394
_refine_diff_density_min         -0.546
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         5171
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0516
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0714P)^2^+0.2625P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1384
_refine_ls_wR_factor_ref         0.1487
_reflns_number_gt                4295
_reflns_number_total             5171
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja300308c_si_001_2.cif
_cod_data_source_block           4b
_cod_database_code               4117681