Two Methods for Direct ortho-Arylation of Benzoic Acids
Hendrich A. Chiong; Quynh-Nhu Pham; Olafs Daugulis; Journal of the American Chemical Society 129 (2007) 9879–9884; doi:10.1021/ja071845e

data_4109758
_publ_section_title
;
 Two Methods for Direct ortho-Arylation of Benzoic Acids
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9879
_journal_page_last               9884
_journal_paper_doi               10.1021/ja071845e
_journal_volume                  129
_journal_year                    2007
_chemical_formula_moiety         'C6 H16 N +, C21 H10 O2 F7 -'
_chemical_formula_sum            'C27 H26 F7 N O2'
_chemical_formula_weight         529.49
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                105.117(2)
_cell_angle_beta                 94.607(3)
_cell_angle_gamma                94.565(3)
_cell_formula_units_Z            4
_cell_length_a                   9.748(2)
_cell_length_b                   12.943(2)
_cell_length_c                   20.949(3)
_cell_measurement_reflns_used    2066
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      23.54
_cell_measurement_theta_min      1.64
_cell_volume                     2529.5(7)
_computing_cell_refinement       'SAINT v7.12A (Bruker-Nonius, 2004)'
_computing_data_collection       'APEX2 v1.0-27 (Bruker-Nonius, 2005)'
_computing_data_reduction        'SAINT v7.12A (Bruker-Nonius, 2004)'
_computing_structure_refinement  'SHELXL v5.10 (G.M. Sheldrick, 1997)'
_computing_structure_solution    'SHELXS v5.10 (G.M. Sheldrick, 1997)'
_diffrn_ambient_temperature      223(2)
_diffrn_detector_area_resol_mean 4K
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker-Nonius APEX II CCD'
_diffrn_measurement_method       CCD
_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  0.0394
_diffrn_reflns_av_sigmaI/netI    0.0917
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            10955
_diffrn_reflns_theta_full        23.54
_diffrn_reflns_theta_max         23.54
_diffrn_reflns_theta_min         1.64
_diffrn_standards_decay_%        0.0
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_T_max  0.9972
_exptl_absorpt_correction_T_min  0.7276
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_description       'Square column'
_exptl_crystal_F_000             1096
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.718
_refine_diff_density_min         -0.633
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.912
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     626
_refine_ls_number_reflns         7424
_refine_ls_number_restraints     11
_refine_ls_restrained_S_all      0.912
_refine_ls_R_factor_all          0.1606
_refine_ls_R_factor_gt           0.0591
_refine_ls_shift/su_max          0.280
_refine_ls_shift/su_mean         0.038
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0815P)^2^+6.5535P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1471
_refine_ls_wR_factor_ref         0.1978
_reflns_number_gt                2626
_reflns_number_total             7424
_reflns_threshold_expression     >4sigma(I)
_cod_data_source_file            ja071845erom20070315_013156.cif
_cod_data_source_block           k1046
_cod_original_cell_volume        2529.5(8)
_cod_database_code               4109758