Iron-Catalyzed Regioselective Direct Oxidative Aryl-Aryl Cross-Coupling
Malapaka Chandrasekharam; Barreddi Chiranjeevi; Kankatala S. V. Gupta; B. Sridhar; Journal of Organic Chemistry 76 (2011) 10229–10235; doi:10.1021/jo202152b

data_4026815
_publ_section_title
;
 Iron-Catalyzed Regioselective Direct Oxidative Aryl-Aryl Cross-Coupling
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              10229
_journal_page_last               10235
_journal_paper_doi               10.1021/jo202152b
_journal_volume                  76
_journal_year                    2011
_chemical_formula_moiety         'C19 H19 N O'
_chemical_formula_sum            'C19 H19 N O'
_chemical_formula_weight         277.35
_chemical_name_systematic
1-(2-(dimethylamino)-4-methylphenyl)naphthalen-2-ol
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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                 104.096(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.302(5)
_cell_length_b                   8.916(4)
_cell_length_c                   19.097(9)
_cell_measurement_reflns_used    3917
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      26.66
_cell_measurement_theta_min      2.26
_cell_volume                     1536.1(13)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 1990)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_measurement_method       '\w scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_sigmaI/netI    0.0268
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10599
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.20
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.199
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.031
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     197
_refine_ls_number_reflns         2707
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0443
_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^)+(0.0727P)^2^+0.2044P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1231
_refine_ls_wR_factor_ref         0.1312
_reflns_number_gt                2177
_reflns_number_total             2707
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo202152b_si_002.cif
_cod_data_source_block           aj72
_cod_original_cell_volume        1536.2(13)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4026815