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_4027074
_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         'C30 H39 N'
_chemical_formula_sum            'C30 H39 N'
_chemical_formula_weight         413.62
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.7385(4)
_cell_length_b                   11.6917(6)
_cell_length_c                   41.5907(19)
_cell_measurement_reflns_used    4785
_cell_measurement_temperature    90.0(5)
_cell_measurement_theta_max      59.0
_cell_measurement_theta_min      4.2
_cell_volume                     4735.5(4)
_computing_cell_refinement       'Bruker (2006) Apex-II '
_computing_data_collection       'Bruker (2006) Apex-II'
_computing_data_reduction        'Bruker (2006) Apex-II '
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'Bruker SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      90.0(5)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_av_sigmaI/netI    0.0309
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_number            15774
_diffrn_reflns_theta_full        59.26
_diffrn_reflns_theta_max         59.3
_diffrn_reflns_theta_min         2.1
_exptl_absorpt_coefficient_mu    0.489
_exptl_absorpt_correction_T_max  0.944
_exptl_absorpt_correction_T_min  0.892
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.160
_exptl_crystal_description       plate
_exptl_crystal_F_000             1808
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.380
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         3376
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.063
_refine_ls_R_factor_gt           0.053
_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^)+(0.0543P)^2^+4.6446P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.132
_refine_ls_wR_factor_ref         0.138
_reflns_number_gt                2857
_reflns_number_total             3376
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo202681r_si_003.cif
_cod_data_source_block           JDD4
_cod_original_sg_symbol_Hall     '-P 2ac 2ab '
_cod_original_sg_symbol_H-M      'P b c a '
_cod_database_code               4027074