Highly selective directed arylation reactions via back-to-back dehydrogenative C-H borylation/arylation reactions
Eric C. Keske; Brandon D. Moore; Olena V. Zenkina; Ruiyao Wang; Gabriele Schatte; Cathleen M. Crudden; Chem.Commun. 50 (2014) 9883–; doi:10.1039/C4cc02499K

data_7115495
_publ_section_title
;
 Highly selective directed arylation reactions via back-to-back
 dehydrogenative C-H borylation/arylation reactions
;
_journal_name_full               Chem.Commun.
_journal_page_first              9883
_journal_paper_doi               10.1039/C4cc02499K
_journal_volume                  50
_journal_year                    2014
_chemical_formula_moiety         'C19 H24 B N O2'
_chemical_formula_sum            'C19 H24 B N O2'
_chemical_formula_weight         309.20
_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'
_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           'manual editing of SHELXL-2013 template'
_cell_angle_alpha                90
_cell_angle_beta                 96.075(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.0448(9)
_cell_length_b                   13.1778(10)
_cell_length_c                   13.6491(12)
_cell_measurement_reflns_used    3207
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      50.353
_cell_measurement_theta_min      5.126
_cell_volume                     1796.6(3)
_computing_cell_refinement
' Saint V8.30A and SADABS V2012/1 (Apex2, v2013.10-0; Bruker AXS)'
_computing_data_collection
' APEX2 software package v2013.10-0 (Bruker AXS)'
_computing_data_reduction
' Saint V8.30A and SADABS V2012/1 (Apex2, v2013.10-0; Bruker AXS'
_computing_molecular_graphics    ' XP (SHELXTL-NT v6.14, Bruker AXS)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2012)'
_computing_structure_solution
; SIR-2004 (M. C. Burla, R. Caliandro, M. Camalli, B. Carrozzini, 
  G. L. Cascarano, L. De Caro, C. Giacovazzo, G. Polidori
  and R. Spagna, 2005)
;
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Smart Apex2 CCD (Bruker AXS)'
_diffrn_measurement_method       'CCD rotation images, \f and \w scans'
_diffrn_radiation_monochromator  'horizontal mounted graphite crystal'
_diffrn_radiation_source         'Bruker AXS K780, fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12196
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.681
_diffrn_reflns_theta_min         2.559
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2012/1 (Apex2, Bruker AXS)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.143
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.324
_exptl_crystal_size_mid          0.258
_exptl_crystal_size_min          0.188
_exptl_transmission_factor_max   0.7457
_exptl_transmission_factor_min   0.7119
_refine_diff_density_max         0.124
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.028
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     278
_refine_ls_number_reflns         3403
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0591
_refine_ls_R_factor_gt           0.0391
_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^)+(0.0476P)^2^+0.2010P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0942
_refine_ls_wR_factor_ref         0.1066
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2475
_reflns_number_total             3403
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4cc02499k2.cif
_cod_data_source_block           ccoz_200a
_cod_database_code               7115495
_shelx_estimated_absorpt_t_min   0.977
_shelx_estimated_absorpt_t_max   0.987
_shelxl_version_number           2012-9
_shelx_res_checksum              83881
_shelx_hkl_checksum              36550