Synthesis of Indolylquinolines, Indolylacridines, and Indolylcyclopenta[b]quinolines from the Baylis-Hillman Adducts: An in Situ [1,3]-Sigmatropic Rearrangement of an Indole Nucleus To Access Indolylacridines and Indolylcyclopenta[b]quinolines
Chintakunta Ramesh; Po-Min Lei; Donala Janreddy; Veerababurao Kavala; Chun-Wei Kuo; Ching-Fa Yao; Journal of Organic Chemistry 77 (2012) 8451–8464; doi:10.1021/jo301313m

data_4027539
_publ_section_title
;
 Synthesis of Indolylquinolines, Indolylacridines, and
 Indolylcyclopenta[b]quinolines from the Baylis-Hillman Adducts: An in
 Situ [1,3]-Sigmatropic Rearrangement of an Indole Nucleus To Access
 Indolylacridines and Indolylcyclopenta[b]quinolines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8451
_journal_page_last               8464
_journal_paper_doi               10.1021/jo301313m
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C22 H20 N2 O3'
_chemical_formula_sum            'C22 H20 N2 O3'
_chemical_formula_weight         360.40
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 91.1850(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.4004(2)
_cell_length_b                   13.9268(3)
_cell_length_c                   17.7637(5)
_cell_measurement_reflns_used    10195
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.028
_cell_measurement_theta_min      2.037
_cell_volume                     1830.40(8)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction        'HKL Denzo and Scalepack'
_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      293(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_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  0.0670
_diffrn_reflns_av_sigmaI/netI    0.0516
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            12761
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.29
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1.2351
_exptl_absorpt_correction_T_min  0.8321
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 ?
;
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_description       prism
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    fixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         3226
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.1078
_refine_ls_R_factor_gt           0.0675
_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^)+(0.1137P)^2^+0.4358P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1778
_refine_ls_wR_factor_ref         0.2044
_reflns_number_gt                2109
_reflns_number_total             3226
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo301313m_si_001.cif
_cod_data_source_block           9999
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4027539