Transition-Metal-Free Direct Arylation: Synthesis of Halogenated 2-Amino-2'-hydroxy-1,1'-biaryls and Mechanism by DFT Calculations
Hongyin Gao; Daniel H. Ess; Muhammed Yousufuddin; László Kürti; Journal of the American Chemical Society 135 (2013) 7086–7089; doi:10.1021/ja400897u

data_4119739
_publ_section_title
;
 Transition-Metal-Free Direct Arylation: Synthesis of Halogenated
 2-Amino-2'-hydroxy-1,1'-biaryls and Mechanism by DFT Calculations
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7086
_journal_page_last               7089
_journal_paper_doi               10.1021/ja400897u
_journal_volume                  135
_journal_year                    2013
_chemical_formula_sum            'C12 H10 Br N O'
_chemical_formula_weight         264.12
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.364(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.6597(12)
_cell_length_b                   13.388(3)
_cell_length_c                   16.692(4)
_cell_measurement_reflns_used    4421
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.17
_cell_measurement_theta_min      2.48
_cell_volume                     1024.3(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0553
_diffrn_reflns_av_sigmaI/netI    0.0486
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9601
_diffrn_reflns_theta_full        28.29
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         1.96
_exptl_absorpt_coefficient_mu    3.982
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_correction_T_min  0.360
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.713
_exptl_crystal_description       needle
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.428
_refine_diff_density_min         -1.353
_refine_diff_density_rms         0.139
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2538
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0397
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0625P)^2^+0.4748P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1019
_refine_ls_wR_factor_ref         0.1083
_reflns_number_gt                2185
_reflns_number_total             2538
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja400897u_si_002.cif
_cod_data_source_block           laszlo7m
_cod_database_code               4119739