Copper(II)-Catalyzed Sequential C,N-Difunctionalization of 1,4-Naphthoquinone for the Synthesis of Benzo[f]indole-4,9-diones under Base-Free Condition
Jin-Wei Sun; Xiang-Shan Wang; Yun Liu; Journal of Organic Chemistry 78 (2013) 10560–10566; doi:10.1021/jo401842d

data_4028688
_publ_section_title
;
 Copper(II)-Catalyzed Sequential C,N-Difunctionalization of
 1,4-Naphthoquinone for the Synthesis of Benzo[f]indole-4,9-diones under
 Base-Free Condition
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              10560
_journal_page_last               10566
_journal_paper_doi               10.1021/jo401842d
_journal_volume                  78
_journal_year                    2013
_chemical_formula_sum            'C31 H19 N O3'
_chemical_formula_weight         453.47
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                63.430(3)
_cell_angle_beta                 69.213(3)
_cell_angle_gamma                73.770(3)
_cell_formula_units_Z            2
_cell_length_a                   10.4834(5)
_cell_length_b                   10.8984(5)
_cell_length_c                   11.9384(6)
_cell_measurement_temperature    296(2)
_cell_volume                     1128.57(10)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0240
_diffrn_reflns_av_sigmaI/netI    0.0219
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15170
_diffrn_reflns_theta_full        25.10
_diffrn_reflns_theta_max         25.10
_diffrn_reflns_theta_min         3.19
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.9830
_exptl_absorpt_correction_T_min  0.9747
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(XCAD4; Harms & Wocadlo, 1995)'
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.131
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.030
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.941
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         4005
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.941
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0363
_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^)+(0.0880P)^2^+0.0953P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1111
_refine_ls_wR_factor_ref         0.1247
_reflns_number_gt                3104
_reflns_number_total             4005
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo401842d_si_002.cif
_cod_data_source_block           a
_cod_original_cell_volume        1128.57(9)
_cod_database_code               4028688