Naphthalene-1,8-diylbis(diphenylmethylium) as an Organic Two-Electron Oxidant: Benzidine Synthesis via Oxidative Self-Coupling of N,N-Dialkylanilines
Terunobu Saitoh; Suguru Yoshida; Junji Ichikawa; Journal of Organic Chemistry 71 (2006) 6414–6419; doi:10.1021/jo060662s

data_4021886
_publ_section_title
;
 Naphthalene-1,8-diylbis(diphenylmethylium) as an Organic
 Two-Electron Oxidant: Benzidine Synthesis via Oxidative Self-Coupling
 of N,N-Dialkylanilines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6414
_journal_page_last               6419
_journal_paper_doi               10.1021/jo060662s
_journal_volume                  71
_journal_year                    2006
_chemical_formula_sum            'C36 H26 Cl2 O8'
_chemical_formula_weight         657.47
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.0000(15)
_cell_angle_beta                 104.6052(17)
_cell_angle_gamma                90.0000(15)
_cell_formula_units_Z            4
_cell_length_a                   16.090(7)
_cell_length_b                   10.544(4)
_cell_length_c                   17.881(7)
_cell_measurement_temperature    120(2)
_cell_volume                     2936(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.749
_diffrn_measured_fraction_theta_max 0.749
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_sigmaI/netI    0.0462
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            16652
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.05
_exptl_absorpt_coefficient_mu    0.279
_exptl_absorpt_correction_T_max  0.9463
_exptl_absorpt_correction_T_min  0.8732
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         1.480
_refine_diff_density_min         -0.773
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     434
_refine_ls_number_reflns         5037
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0593
_refine_ls_R_factor_gt           0.0527
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0837P)^2^+2.5555P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1420
_refine_ls_wR_factor_ref         0.1467
_reflns_number_gt                4415
_reflns_number_total             5037
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo060662ssi20060328_040822.cif
_cod_original_sg_symbol_H-M      'P 21/a'
_cod_database_code               4021886