Regioselective Copper-Catalyzed Boracarboxylation of Vinyl Arenes.
Butcher, Trevor W.; McClain, Edward J.; Hamilton, Tyler G.; Perrone, Trina M.; Kroner, Kayla M.; Donohoe, Gregory C.; Akhmedov, Novruz G.; Petersen, Jeffrey L.; Popp, Brian V.; Organic letters 18 (2016) 6428–6431; doi:10.1021/acs.orglett.6b03326

data_1555973
_publ_section_title
;
 Regioselective Copper-Catalyzed Boracarboxylation of Vinyl Arenes.
;
_journal_issue                   24
_journal_name_full               'Organic letters'
_journal_page_first              6428
_journal_page_last               6431
_journal_paper_doi               10.1021/acs.orglett.6b03326
_journal_volume                  18
_journal_year                    2016
_chemical_formula_sum            'C19 H29 B O4'
_chemical_formula_weight         332.23
_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'
_atom_sites_solution_hydrogens   mixed
_cell_angle_alpha                90
_cell_angle_beta                 114.1484(19)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.8565(7)
_cell_length_b                   16.1793(11)
_cell_length_c                   12.2433(9)
_cell_measurement_reflns_used    5314
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      27.4942
_cell_measurement_theta_min      3.1091
_cell_volume                     1962.3(2)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker AXS D8 Venture fixed chi'
_diffrn_measurement_method       'omega scan, PHOTON 100 CMOS'
_diffrn_radiation_monochromator  Triumph
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            9820
_diffrn_reflns_theta_full        27.53
_diffrn_reflns_theta_max         27.53
_diffrn_reflns_theta_min         3.11
_diffrn_source_type              'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.95
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/3 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.125
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       polyhedral
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.572
_exptl_crystal_size_mid          0.376
_exptl_crystal_size_min          0.296
_refine_diff_density_max         0.479
_refine_diff_density_min         -0.277
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         4463
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0828
_refine_ls_R_factor_gt           0.0599
_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^)+(0.0796P)^2^+1.4928P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1513
_refine_ls_wR_factor_ref         0.1699
_reflns_number_gt                3341
_reflns_number_total             4463
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b03326_si_001.cif
_cod_data_source_block           I
_cod_database_code               1555973
_shelx_res_checksum              59946
_shelx_hkl_checksum              28215