Oxidative skeletal rearrangement of 1,1'-binaphthalene-2,2'-diamines (BINAMs) via C-C bond cleavage and nitrogen migration: a versatile synthesis of U-shaped azaacenes
Youhei Takeda; Masato Okazaki; Satoshi Minakata; Chem.Commun. 50 (2014) 10291–; doi:10.1039/C4cc04911J

data_7115549
_publ_section_title
;
 Oxidative skeletal rearrangement of 1,1'-binaphthalene-2,2'-diamines
 (BINAMs) via C-C bond cleavage and nitrogen migration: a versatile
 synthesis of U-shaped azaacenes
;
_journal_name_full               Chem.Commun.
_journal_page_first              10291
_journal_paper_doi               10.1039/C4cc04911J
_journal_volume                  50
_journal_year                    2014
_chemical_formula_moiety         'C20 H12 N2'
_chemical_formula_sum            'C20 H12 N2'
_chemical_formula_weight         280.33
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   3.88126(10)
_cell_length_b                   11.6430(3)
_cell_length_c                   29.5312(8)
_cell_measurement_reflns_used    10182
_cell_measurement_temperature    277
_cell_measurement_theta_max      68.27
_cell_measurement_theta_min      3.00
_cell_volume                     1334.50(6)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      277
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            15392
_diffrn_reflns_theta_full        68.20
_diffrn_reflns_theta_max         68.20
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.645
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_correction_T_min  0.878
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             584.00
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.190
_refine_ls_extinction_coef       0.0048(7)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2436
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0503
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0682P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1344
_reflns_number_gt                1471
_reflns_number_total             2436
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            c4cc04911j2.cif
_cod_data_source_block           120120okazaki
_cod_database_code               7115549