Rhenium-catalysed dehydrogenative borylation of primary and secondary C(sp^3^)-H bonds adjacent to a nitrogen atom
Masahito Murai; Tetsuya Omura; Yoichiro Kuninobu; Kazuhiko Takai; Chem.Commun. 51 (2015) 4583–; doi:10.1039/C4cc09508A

data_7116659
_publ_section_title
;
 Rhenium-catalysed dehydrogenative borylation of primary and secondary
 C(sp^3^)-H bonds adjacent to a nitrogen atom
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_journal_name_full               Chem.Commun.
_journal_page_first              4583
_journal_paper_doi               10.1039/C4cc09508A
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         'C15 H22 B F N2'
_chemical_formula_sum            'C15 H22 B F N2'
_chemical_formula_weight         260.16
_chemical_melting_point          383.5(5)
_chemical_name_common            murai-sp3-B-F
_chemical_name_systematic
'[N-(9-Borabicyclo[3.3.1]non-9-ylmethyl)-5-fluoropyridin-2-yl]-N-methylamine'
_chemical_properties_physical    Acid-sensitive
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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_update_record
;
2014-11-26 deposited with the CCDC.
2015-02-05 downloaded from the CCDC.
;
_cell_angle_alpha                75.80(4)
_cell_angle_beta                 76.99(4)
_cell_angle_gamma                75.35(4)
_cell_formula_units_Z            2
_cell_length_a                   7.486(7)
_cell_length_b                   9.564(9)
_cell_length_c                   10.597(11)
_cell_measurement_reflns_used    1743
_cell_measurement_temperature    293
_cell_measurement_theta_max      27.40
_cell_measurement_theta_min      3.20
_cell_volume                     700.8(12)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r16'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r16'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293
_diffrn_detector_area_resol_mean 7.111
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0863
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11219
_diffrn_reflns_theta_full        27.43
_diffrn_reflns_theta_max         27.43
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.851
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             280.00
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.260
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.218
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     172
_refine_ls_number_reflns         3173
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.1194
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0408P)^2^+0.3862P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1989
_reflns_number_gt                2008
_reflns_number_total             3173
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            c4cc09508a2.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '383-384' was changed to '383.5(5)' -
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 2827 2014-09-09 07:05:25Z andrius 
;
_cod_database_code               7116659