<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_4127984
_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_absolute_configuration ad
_chemical_formula_moiety         'C16 H36 N +, C6 H5 Cl N O3 S -'
_chemical_formula_sum            'C22 H41 Cl N2 O3 S'
_chemical_formula_weight         449.08
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 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                90
_cell_angle_beta                 109.073(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.1658(5)
_cell_length_b                   14.5252(5)
_cell_length_c                   14.8017(8)
_cell_measurement_reflns_used    9910
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      66.89
_cell_measurement_theta_min      4.91
_cell_volume                     2472.03(19)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0313
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14015
_diffrn_reflns_point_group_measured_fraction_full 0.947
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        66.885
_diffrn_reflns_theta_max         66.885
_diffrn_reflns_theta_min         4.905
_diffrn_source                   'Incoatec I\mS Cu microsource'
_exptl_absorpt_coefficient_mu    2.342
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6595
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.207
_exptl_crystal_description       block
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.373
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
;
Flack x determined using 1742 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.047(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     270
_refine_ls_number_reflns         4180
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0350
_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^)+(0.0591P)^2^+0.6404P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0902
_refine_ls_wR_factor_ref         0.0916
_reflns_Friedel_coverage         0.893
_reflns_Friedel_fraction_full    0.896
_reflns_Friedel_fraction_max     0.896
_reflns_number_gt                3989
_reflns_number_total             4180
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b07267_si_002.cif
_cod_data_source_block           RP_B1_0015
_cod_database_code               4127984
_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             MM977
_cambridge_data_id               RP_B1_0015
_ccdc_publ_extra_info
;
_cambridge_sample_id MM977
_cambridge_data_id RP_B1_0015
;
_shelx_estimated_absorpt_t_min   0.678
_shelx_estimated_absorpt_t_max   0.766