Mechanistic Studies into Amine-Mediated Electrophilic Arene Borylation and Its Application in MIDA Boronate Synthesis
Viktor Bagutski; Alessandro Del Grosso; Josue Ayuso Carrillo; Ian A. Cade; Matthew D. Helm; James R. Lawson; Paul J. Singleton; Sophia A. Solomon; Tommaso Marcelli; Michael J. Ingleson; Journal of the American Chemical Society 135 (2013) 474–487; doi:10.1021/ja3100963

data_4119160
_publ_section_title
;
 Mechanistic Studies into Amine-Mediated Electrophilic Arene Borylation
 and Its Application in MIDA Boronate Synthesis
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              474
_journal_page_last               487
_journal_paper_doi               10.1021/ja3100963
_journal_volume                  135
_journal_year                    2013
_chemical_formula_moiety         'C24 H58 Al2 Cl6 N2 O4'
_chemical_formula_sum            'C24 H58 Al2 Cl6 N2 O4'
_chemical_formula_weight         705.38
_chemical_name_systematic
; 
 ? 
;
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_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 104.612(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.8521(4)
_cell_length_b                   11.4984(4)
_cell_length_c                   13.7899(5)
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.48
_cell_measurement_theta_min      3.05
_cell_volume                     1818.51(11)
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
;
_computing_data_collection
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CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
;
_computing_data_reduction
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CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
;
_computing_molecular_graphics    'SHELXL-97 (Sheldrick, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3367
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Oxford Diffraction XCalibur 2'
_diffrn_measurement_method       'phi and omega'
_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  0.0447
_diffrn_reflns_av_sigmaI/netI    0.0560
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10738
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         3.86
_exptl_absorpt_coefficient_mu    0.551
_exptl_absorpt_correction_T_max  0.9470
_exptl_absorpt_correction_T_min  0.7335
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_description       needle
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.901
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         3206
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.901
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0320
_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^)+(0.0341P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0681
_refine_ls_wR_factor_ref         0.0705
_reflns_number_gt                2327
_reflns_number_total             3206
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja3100963_si_002_1.cif
_cod_data_source_block           omji71
_cod_database_code               4119160