<i>Para</i>-Selective C-H Borylation of Common Arene Building Blocks Enabled by Ion-Pairing with a Bulky Countercation.
Mihai, Madalina T.; Williams, Benjamin D.; Phipps, Robert J.; Journal of the American Chemical Society 141 (2019) 15477–15482; doi:10.1021/jacs.9b07267

data_4127986
_publ_section_title
;
 <i>Para</i>-Selective C-H Borylation of Common Arene Building Blocks
 Enabled by Ion-Pairing with a Bulky Countercation.
;
_journal_issue                   39
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15477
_journal_page_last               15482
_journal_paper_doi               10.1021/jacs.9b07267
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety         'C16 H36 N +, C7 H7 Cl N O3 S -'
_chemical_formula_sum            'C23 H43 Cl N2 O3 S'
_chemical_formula_weight         463.10
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/1
_cell_angle_alpha                89.052(4)
_cell_angle_beta                 75.296(4)
_cell_angle_gamma                87.331(3)
_cell_formula_units_Z            4
_cell_length_a                   10.0834(6)
_cell_length_b                   15.2873(8)
_cell_length_c                   17.3470(9)
_cell_measurement_reflns_used    4299
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      66.40
_cell_measurement_theta_min      3.90
_cell_volume                     2583.6(2)
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2016)'
_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 0.977
_diffrn_measured_fraction_theta_max 0.977
_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  0.1545
_diffrn_reflns_av_unetI/netI     0.1472
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            8836
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.103
_diffrn_reflns_theta_max         67.103
_diffrn_reflns_theta_min         2.633
_diffrn_source                   'Incoatec I\mS Cu microsource'
_exptl_absorpt_coefficient_mu    2.255
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6110
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'TWINABS (Bruker, 2012)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.191
_exptl_crystal_description       block
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.644
_refine_diff_density_min         -0.478
_refine_diff_density_rms         0.115
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     543
_refine_ls_number_reflns         8836
_refine_ls_number_restraints     312
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.1898
_refine_ls_R_factor_gt           0.1170
_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^)+13.8987P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2068
_refine_ls_wR_factor_ref         0.2452
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5620
_reflns_number_total             8836
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b07267_si_004.cif
_cod_data_source_block           RP_B1_0013
_cod_database_code               4127986
_cambridge_user_name             'Madalina Mihai'
_cambridge_user_crsid            mtm52
_cambridge_supervisor_name       'Robert Phipps'
_cambridge_supervisor_crsid      rjp71
_cambridge_crystallographer_name 'Andrew Bond'
_cambridge_crystallographer_crsid adb29
_cambridge_sample_id             MM979
_cambridge_data_id               RP_B1_0013
_ccdc_publ_extra_info
;
_cambridge_sample_id MM979
_cambridge_data_id RP_B1_0013
;
_shelx_estimated_absorpt_t_min   0.743
_shelx_estimated_absorpt_t_max   0.915