An efficient one-pot, three-component synthesis of indeno[1,2-b]quinoline-9,11(6H,10H)-dione, acridine-1,8(2H,5H)-dione and quinoline-3-carbonitrile derivatives from enaminones.
Tu, Shu-Jiang; Jiang, Bo; Jia, Run-Hong; Zhang, Jun-Yong; Zhang, Yan; Yao, Chang-Sheng; Shi, Feng; Organic & biomolecular chemistry 4 (2006) 3664–3668; doi:10.1039/b607575d

data_7151281
_publ_section_title
;
 An efficient one-pot, three-component synthesis of
 indeno[1,2-b]quinoline-9,11(6H,10H)-dione, acridine-1,8(2H,5H)-dione
 and quinoline-3-carbonitrile derivatives from enaminones.
;
_journal_issue                   19
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3664
_journal_page_last               3668
_journal_paper_doi               10.1039/b607575d
_journal_volume                  4
_journal_year                    2006
_chemical_formula_moiety         'C34 H34 N O5.50'
_chemical_formula_sum            'C34 H34 N O5.5'
_chemical_formula_weight         544.62
_chemical_melting_point          472.0(10)
_chemical_name_systematic
;
7,8-dihydro-10-(3,4,5-trimethoxyphenyl)-7,7-dimethyl-5-p-tolyl-
5H-indeno[1,2-b]quinoline-9,11(6H,10H)-dione
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 103.926(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   25.094(6)
_cell_length_b                   12.755(3)
_cell_length_c                   19.891(5)
_cell_measurement_reflns_used    1509
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      20.16
_cell_measurement_theta_min      2.188
_cell_volume                     6179(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART (Bruker, 1998)'
_computing_data_reduction        'Bruker SAINT (Bruker, 1999)'
_computing_molecular_graphics    'Bruker SHELXTL (Bruker, 1999)'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0974
_diffrn_reflns_av_sigmaI/netI    0.1356
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            15711
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.62
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.9797
_exptl_absorpt_correction_T_min  0.9615
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.171
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2312
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.676
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     378
_refine_ls_number_reflns         5381
_refine_ls_number_restraints     180
_refine_ls_restrained_S_all      0.995
_refine_ls_R_factor_all          0.1921
_refine_ls_R_factor_gt           0.0731
_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^)+(0.1027P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1771
_refine_ls_wR_factor_ref         0.2391
_reflns_number_gt                2112
_reflns_number_total             5381
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b607575d.txt
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/adriana/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1555 2011-01-17 13:19:09Z saulius 

The following automatic conversions were performed:

'_chemical_melting_point' value '471-473' was changed to '472.0(10)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1569 2011-02-09 13:29:24Z adriana 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_original_formula_sum        'C34 H34 N O5.50'
_cod_database_code               7151281