Synthesis of Biologically Active Indenoisoquinoline Derivatives via a One-Pot Copper(II)-Catalyzed Tandem Reaction.
Huang, Chia-Yu; Kavala, Veerababurao; Kuo, Chun-Wei; Konala, Ashok; Yang, Tang-Hao; Yao, Ching-Fa; The Journal of organic chemistry 82 (2017) 1961–1968; doi:10.1021/acs.joc.6b02814

data_4032175
_publ_section_title
;
 Synthesis of Biologically Active Indenoisoquinoline Derivatives via a
 One-Pot Copper(II)-Catalyzed Tandem Reaction.
;
_journal_issue                   4
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1961
_journal_page_last               1968
_journal_paper_doi               10.1021/acs.joc.6b02814
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C23 H14 Cl N O2'
_chemical_formula_sum            'C23 H14 Cl N O2'
_chemical_formula_weight         371.80
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.313(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   19.969(3)
_cell_length_b                   12.545(2)
_cell_length_c                   14.105(3)
_cell_measurement_reflns_used    3821
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.08
_cell_measurement_theta_min      2.34
_cell_volume                     3512.0(11)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX2'
_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  0.0573
_diffrn_reflns_av_sigmaI/netI    0.0651
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            23530
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         1.03
_exptl_absorpt_coefficient_mu    0.236
_exptl_absorpt_correction_T_max  0.9883
_exptl_absorpt_correction_T_min  0.8772
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1536
_exptl_crystal_size_max          0.57
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.572
_refine_diff_density_min         -0.482
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     487
_refine_ls_number_reflns         6152
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.1427
_refine_ls_R_factor_gt           0.0847
_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^)+(0.1315P)^2^+7.0934P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2668
_refine_ls_wR_factor_ref         0.3061
_reflns_number_gt                3432
_reflns_number_total             6152
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo6b02814_si_002.cif
_cod_data_source_block           18218
_cod_depositor_comments
'Adding full bibliography for 4032175--4032176.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4032175