Unexpected 5,6,7,8,9,10-Hexahydro-6,6-pentamethylenephenanthridines and 2,3,4,5-Tetrahydro-4,4-tetramethylene-1H-cyclopenta[c]quinolines from Skraup-Doebner-Von Miller Quinoline Synthesis and Their Implications for the Mechanism of That Reaction
Jean Fotie; Hilaire V. Kemami Wangun; Frank R. Fronczek; Nancy Massawe; Bijay T. Bhattarai; Jessica L. Rhodus; Thomas A. Singleton; D. Scott Bohle; Journal of Organic Chemistry 77 (2012) 2784–2790; doi:10.1021/jo202681r

data_4027073
_publ_section_title
;
 Unexpected 5,6,7,8,9,10-Hexahydro-6,6-pentamethylenephenanthridines and
 2,3,4,5-Tetrahydro-4,4-tetramethylene-1H-cyclopenta[c]quinolines from
 Skraup-Doebner-Von Miller Quinoline Synthesis and Their Implications for
 the Mechanism of That Reaction
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2784
_journal_page_last               2790
_journal_paper_doi               10.1021/jo202681r
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C26 H35 N O'
_chemical_formula_sum            'C26 H35 N O'
_chemical_formula_weight         377.55
_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
_cell_angle_beta                 92.327(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.545(3)
_cell_length_b                   10.021(2)
_cell_length_c                   11.5921(15)
_cell_measurement_reflns_used    5022
_cell_measurement_temperature    95.0(5)
_cell_measurement_theta_max      27.8
_cell_measurement_theta_min      2.5
_cell_volume                     2152.5(6)
_computing_cell_refinement
'Denzo and Scalepack (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2000)'
_computing_data_reduction
'Denzo and Scalepack (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'direct_methods (SIR, Altomare, et al., 1999)'
_diffrn_ambient_temperature      95.0(5)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'Nonius KappaCCD'
_diffrn_measurement_method       ' \w and \f 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  0.0337
_diffrn_reflns_av_sigmaI/netI    0.0460
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            25068
_diffrn_reflns_theta_full        25.25
_diffrn_reflns_theta_max         27.9
_diffrn_reflns_theta_min         2.6
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.165
_exptl_crystal_description       fragment
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.003(1)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     287
_refine_ls_number_reflns         5106
_refine_ls_number_restraints     16
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0833
_refine_ls_R_factor_gt           0.0499
_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^)+(0.0488P)^2^+0.6640P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1113
_refine_ls_wR_factor_ref         0.1265
_reflns_number_gt                3460
_reflns_number_total             5106
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo202681r_si_002.cif
_cod_data_source_block           JDD1
_cod_original_sg_symbol_H-M      'P 21/c '
_cod_database_code               4027073