Regioselective electrophilic borylation of haloarenes.
Del Grosso, Alessandro; Ayuso Carrillo, Josue; Ingleson, Michael J.; Chemical communications (Cambridge, England) 51 (2015) 2878–; doi:10.1039/c4cc10153g

data_7116289
_publ_section_title
;
 Regioselective electrophilic borylation of haloarenes.
;
_journal_issue                   14
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2878
_journal_paper_doi               10.1039/c4cc10153g
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         'C12 H15 B Br F O2'
_chemical_formula_sum            'C12 H15 B Br F O2'
_chemical_formula_weight         300.96
_chemical_name_systematic
;
 2-(4-bromo-2-fluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-12-10
_audit_creation_method
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  Olex2 1.2
  (compiled Apr 23 2013 17:59:47, GUI svn.r4466)
;
_audit_update_record
;
2014-12-10 deposited with the CCDC.
2015-01-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.002(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.8821(8)
_cell_length_b                   7.6711(4)
_cell_length_c                   12.4528(6)
_cell_measurement_reflns_used    1769
_cell_measurement_temperature    150
_cell_measurement_theta_max      26.9800
_cell_measurement_theta_min      4.2030
_cell_volume                     1325.30(12)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_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_environment      N~2~
_diffrn_ambient_temperature      150.0
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0714
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9956
_diffrn_measured_fraction_theta_max 0.8698
_diffrn_measurement_details
;
  1 omega    4.00   80.00   1.0000    1.1050
omega____ theta____ kappa____ phi______ frames
    -       19.4509   57.0000  -60.0000 76

  2 omega   53.00   80.00   1.0000    1.1050
omega____ theta____ kappa____ phi______ frames
    -       19.4509  178.0000   90.0000 27

  3 omega  -20.00   86.00   1.0000    1.1050
omega____ theta____ kappa____ phi______ frames
    -       19.4509   19.0000  -90.0000 106

  4 omega  -95.00  -69.00   1.0000    1.1050
omega____ theta____ kappa____ phi______ frames
    -      -18.3571  178.0000  120.0000 26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0225609000
_diffrn_orient_matrix_UB_12      -0.0472052000
_diffrn_orient_matrix_UB_13      0.0429344000
_diffrn_orient_matrix_UB_21      0.0456486000
_diffrn_orient_matrix_UB_22      0.0158832000
_diffrn_orient_matrix_UB_23      -0.0218961000
_diffrn_orient_matrix_UB_31      0.0043379000
_diffrn_orient_matrix_UB_32      0.0779031000
_diffrn_orient_matrix_UB_33      0.0304675000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0432
_diffrn_reflns_av_unetI/netI     0.0791
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.868
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5945
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.868
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.865
_diffrn_reflns_theta_min         3.424
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    3.100
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56386
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_description       irregular
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.767
_refine_diff_density_min         -0.774
_refine_diff_density_rms         0.108
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         3024
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0747
_refine_ls_R_factor_gt           0.0523
_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^)+(0.0395P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0995
_refine_ls_wR_factor_ref         0.1105
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2315
_reflns_number_total             3024
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4cc10153g2.cif
_cod_data_source_block           amji235a
_cod_depositor_comments
'Adding full bibliography for 7116287--7116290.cif.'
_cod_database_code               7116289
_chemical_oxdiff_formula         C12H15B1Br1F1O2
_reflns_odcompleteness_completeness 99.56
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H6(0.023) H9A(0.048) H9B(0.048) H9C(0.048) H5(0.029) H3(0.025)
 H12A(0.047) H12B(0.047) H12C(0.047) H8A(0.045) H8B(0.045) H8C(0.045)
 H11A(0.053) H11B(0.053) H11C(0.053)
 Fixed X: H6(0.917) H9A(0.5026) H9B(0.5289) H9C(0.5999) H5(1.0181) H3(0.8078)
 H12A(0.6935) H12B(0.6571) H12C(0.7701) H8A(0.5734) H8B(0.5238) H8C(0.4831)
 H11A(0.8042) H11B(0.695) H11C(0.74)
 Fixed Y: H6(0.0953) H9A(0.0094) H9B(-0.1229) H9C(0.0353) H5(0.2963)
 H3(0.4033) H12A(-0.164) H12B(-0.3598) H12C(-0.318) H8A(-0.356) H8B(-0.3855)
 H8C(-0.2393) H11A(-0.4371) H11B(-0.503) H11C(-0.3845)
 Fixed Z: H6(0.4413) H9A(0.3578) H9B(0.2639) H9C(0.2943) H5(0.5285) H3(0.7369)
 H12A(0.2042) H12B(0.2208) H12C(0.2227) H8A(0.5127) H8B(0.3961) H8C(0.4742)
 H11A(0.4009) H11B(0.4053) H11C(0.5001)
;
_shelxl_version_number           2014-3