Copper(II)-Catalyzed Synthesis of Benzo[f]pyrido[1,2-a]indole-6,11-dione Derivatives via Naphthoquinone Difunctionalization Reaction
Yun Liu; Jin-Wei Sun; Journal of Organic Chemistry 77 (2012) 1191–1197; doi:10.1021/jo2023312

data_4026907
_publ_contact_author_address
;
School of Chemistry and Chemical Engineering,
Xuzhou Normal University, Xuzhou,
Jiangsu 221116, People's Republic of China
;
_publ_contact_author_email       liu__yun3@sina.com.cn
_publ_contact_author_name        'Yun Liu'
_publ_section_title
;
 Copper(II)-Catalyzed Synthesis of Benzo[f]pyrido[1,2-a]indole-6,11-dione
 Derivatives via Naphthoquinone Difunctionalization Reaction
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1191
_journal_page_last               1197
_journal_paper_doi               10.1021/jo2023312
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C24 H14 Cl N O3'
_chemical_formula_sum            'C24 H14 Cl N O3'
_chemical_formula_weight         399.81
_chemical_melting_point          553
_chemical_name_systematic
; 
 12-(4-Chlorobenzoyl)-2-methylbenzo[f]pyrido[1,2-a]indole-6, 11-dione
;
_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
_audit_update_record
;
2011-01-18 # Formatted by publCIF
;
_cell_angle_alpha                73.78(3)
_cell_angle_beta                 84.08(3)
_cell_angle_gamma                80.89(3)
_cell_formula_units_Z            2
_cell_length_a                   7.5000(15)
_cell_length_b                   10.077(2)
_cell_length_c                   12.947(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      12
_cell_measurement_theta_min      9
_cell_volume                     925.9(4)
_computing_cell_refinement       'CAD4 Software'
_computing_data_collection       'CAD4 Software (Enraf-Nonius, 1989)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  'SHELXTL and PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       \w/2\q
_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  0.0175
_diffrn_reflns_av_sigmaI/netI    0.0379
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3519
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.64
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.233
_exptl_absorpt_correction_T_max  0.9771
_exptl_absorpt_correction_T_min  0.9548
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(XCAD4; Harms & Wocadlo, 1995)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_description       block
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3245
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0784
_refine_ls_R_factor_gt           0.0489
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0605P)^2^+0.0828P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1131
_refine_ls_wR_factor_ref         0.1237
_reflns_number_gt                2236
_reflns_number_total             3245
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo2023312_si_002.cif
_cod_data_source_block           x
_cod_original_cell_volume        925.9(3)
_cod_database_code               4026907