Reaction of Quinones and Guanidine Derivatives: Simple Access to Bis-2-aminobenzimidazole Moiety of Benzosceptrin and Other Benzazole Motifs.
Tran, Minh Quan; Ermolenko, Ludmila; Retailleau, Pascal; Nguyen, Thanh Binh; Al-Mourabit, Ali; Organic letters 16 (2014) 920–923; doi:10.1021/ol403672p

data_1513498
_publ_section_title
;
 Reaction of Quinones and Guanidine Derivatives: Simple Access to
 Bis-2-aminobenzimidazole Moiety of Benzosceptrin and Other Benzazole
 Motifs.
;
_journal_issue                   3
_journal_name_full               'Organic letters'
_journal_page_first              920
_journal_page_last               923
_journal_paper_doi               10.1021/ol403672p
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C19 H15 N3 O, C7 H8'
_chemical_formula_sum            'C26 H23 N3 O'
_chemical_formula_weight         393.47
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                89.375(5)
_cell_angle_beta                 84.600(4)
_cell_angle_gamma                76.159(4)
_cell_formula_units_Z            4
_cell_length_a                   10.794(2)
_cell_length_b                   12.496(3)
_cell_length_c                   16.394(3)
_cell_measurement_reflns_used    6531
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.028
_cell_measurement_theta_min      0.407
_cell_volume                     2137.4(8)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997); COLLECT (Nonius B.V., 1999)'
_computing_data_collection
'DENZO (Otwinowski & Minor, 1997); COLLECT (Nonius B.V., 1999)'
_computing_data_reduction        'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement
'SHELXL97 (Sheldrick, 2008); CRYSTALBUILDER (Welter, 2006)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Nonius kappa-CCD diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_sigmaI/netI    0.0512
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            19929
_diffrn_reflns_theta_full        25.04
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_min         2.99
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Nonius Kappa CCD'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.88
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Scalepack (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     614
_refine_ls_number_reflns         7472
_refine_ls_number_restraints     102
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0968
_refine_ls_R_factor_gt           0.0629
_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^)+(0.0986P)^2^+0.5438P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1625
_refine_ls_wR_factor_ref         0.1880
_reflns_number_gt                5104
_reflns_number_total             7483
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol403672p_si_001.cif
_cod_data_source_block           b0321
_cod_database_code               1513498