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_4027072
_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         'C24 H30 Cl N'
_chemical_formula_sum            'C24 H30 Cl N'
_chemical_formula_weight         367.94
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                97.344(6)
_cell_angle_beta                 98.122(8)
_cell_angle_gamma                111.627(8)
_cell_formula_units_Z            2
_cell_length_a                   8.1800(10)
_cell_length_b                   9.9875(13)
_cell_length_c                   13.2073(15)
_cell_measurement_reflns_used    6632
_cell_measurement_temperature    95.0(5)
_cell_measurement_theta_max      33.1
_cell_measurement_theta_min      2.5
_cell_volume                     973.8(2)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'COLLECT (Nonius, 2000)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare  et al., 1999)'
_diffrn_ambient_temperature      95.0(5)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_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  0.0318
_diffrn_reflns_av_sigmaI/netI    0.0468
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            24648
_diffrn_reflns_theta_full        25.25
_diffrn_reflns_theta_max         33.1
_diffrn_reflns_theta_min         2.8
_exptl_absorpt_coefficient_mu    0.204
_exptl_absorpt_correction_T_max  0.957
_exptl_absorpt_correction_T_min  0.951
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'HKL Scalepack (Otwinowski & Minor 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_description       fragment
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.541
_refine_diff_density_min         -0.578
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         7378
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.063
_refine_ls_R_factor_gt           0.044
_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^)+(0.0525P)^2^+0.2649P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.108
_refine_ls_wR_factor_ref         0.118
_reflns_number_gt                5686
_reflns_number_total             7378
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo202681r_si_001.cif
_cod_data_source_block           JDD3-2
_cod_original_sg_symbol_H-M      'P -1 '
_cod_database_code               4027072