Ion Pair-Directed Regiocontrol in Transition-Metal Catalysis: A Meta-Selective C-H Borylation of Aromatic Quaternary Ammonium Salts.
Davis, Holly J.; Mihai, Madalina T.; Phipps, Robert J.; Journal of the American Chemical Society 138 (2016) 12759–12762; doi:10.1021/jacs.6b08164

data_4130965
_publ_section_title
;
 Ion Pair-Directed Regiocontrol in Transition-Metal Catalysis: A
 Meta-Selective C-H Borylation of Aromatic Quaternary Ammonium Salts.
;
_journal_issue                   39
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12759
_journal_page_last               12762
_journal_paper_doi               10.1021/jacs.6b08164
_journal_volume                  138
_journal_year                    2016
_chemical_formula_moiety
'C21 H35 B2 F N O4 +, C7 H7 O3 S -, 2(C H2 Cl2)'
_chemical_formula_sum            'C30 H46 B2 Cl4 F N O7 S'
_chemical_formula_weight         747.16
_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_Hall           '-C 2y'
_space_group_name_H-M_alt        'C 1 2/m 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 106.700(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   33.5416(10)
_cell_length_b                   7.4594(2)
_cell_length_c                   15.8608(5)
_cell_measurement_reflns_used    9438
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      66.72
_cell_measurement_theta_min      2.75
_cell_volume                     3801.0(2)
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8-QUEST PHOTON-100'
_diffrn_measurement_method       '\w and \f-scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            18136
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        66.915
_diffrn_reflns_theta_max         66.915
_diffrn_reflns_theta_min         2.751
_diffrn_source                   'Incoatec I\mS Cu microsource'
_exptl_absorpt_coefficient_mu    3.740
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.5600
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_description       plate
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.831
_refine_diff_density_min         -1.001
_refine_diff_density_rms         0.096
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         3644
_refine_ls_number_restraints     90
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.1111
_refine_ls_R_factor_gt           0.0943
_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^)+(0.1615P)^2^+15.3069P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2727
_refine_ls_wR_factor_ref         0.2915
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2857
_reflns_number_total             3644
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b08164_si_001.cif
_cod_data_source_block           RP_B1_0004
_cod_original_sg_symbol_H-M      'C 2/m'
_cod_database_code               4130965
_cambridge_user_name             'Holly Davis'
_cambridge_user_crsid            hd308
_cambridge_supervisor_name       'Robert Phipps'
_cambridge_supervisor_crsid      rjp71
_cambridge_crystallographer_name 'Andrew Bond'
_cambridge_crystallographer_crsid adb29
_cambridge_sample_id             HD503A
_cambridge_data_id               RP_B1_0004
_ccdc_publ_extra_info
;
_cambridge_sample_id HD503A
_cambridge_data_id RP_B1_0004
;
_shelx_estimated_absorpt_t_min   0.493
_shelx_estimated_absorpt_t_max   0.896
_shelx_res_checksum              83513
_shelx_hkl_checksum              77207