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_7116290
_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 Cl F O2'
_chemical_formula_sum            'C12 H15 B Cl F O2'
_chemical_formula_weight         256.50
_chemical_name_systematic
;
2-(4-chloro-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
;
  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                 92.422(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.8661(7)
_cell_length_b                   7.5020(4)
_cell_length_c                   12.4291(8)
_cell_measurement_reflns_used    1463
_cell_measurement_temperature    150
_cell_measurement_theta_max      26.7100
_cell_measurement_theta_min      3.5370
_cell_volume                     1291.76(13)
_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)
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_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
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0714
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9955
_diffrn_measured_fraction_theta_max 0.8590
_diffrn_measurement_details
;
  1 omega  -94.00   10.00   1.0000    1.1000
omega____ theta____ kappa____ phi______ frames
    -      -20.4767  -37.0000 -150.0000 104

  2 omega  -25.00   55.00   1.0000    1.1000
omega____ theta____ kappa____ phi______ frames
    -      -20.4767   19.0000   30.0000 80

  3 omega  -45.00    0.00   1.0000    1.1000
omega____ theta____ kappa____ phi______ frames
    -       21.6485  -57.0000  120.0000 45
;
_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      0.0438674000
_diffrn_orient_matrix_UB_12      0.0102686000
_diffrn_orient_matrix_UB_13      -0.0267789000
_diffrn_orient_matrix_UB_21      -0.0184841000
_diffrn_orient_matrix_UB_22      0.0781694000
_diffrn_orient_matrix_UB_23      -0.0255396000
_diffrn_orient_matrix_UB_31      0.0189672000
_diffrn_orient_matrix_UB_32      0.0521257000
_diffrn_orient_matrix_UB_33      0.0434723000
_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  0.0343
_diffrn_reflns_av_unetI/netI     0.0710
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.855
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5252
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.855
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.861
_diffrn_reflns_theta_min         3.281
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.294
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80940
_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    1.319
_exptl_crystal_description       irregular
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         2898
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0837
_refine_ls_R_factor_gt           0.0547
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0367P)^2^+0.4215P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1038
_refine_ls_wR_factor_ref         0.1230
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2005
_reflns_number_total             2898
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4cc10153g2.cif
_cod_data_source_block           amji207
_cod_depositor_comments
'Adding full bibliography for 7116287--7116290.cif.'
_cod_original_cell_volume        1291.77(12)
_cod_database_code               7116290
_chemical_oxdiff_formula         C12H15B1Cl1F1O2
_reflns_odcompleteness_completeness 99.55
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C2(H2), C5(H5)
2.b Idealised Me refined as rotating group:
 C9(H9a,H9b,H9c), C11(H11a,H11b,H11c), C8(H8a,H8b,H8c), C12(H12a,H12b,H12c)
;
_shelxl_version_number           2014-3