Preparation and Cycloaddition Reactions of Enantiopure 2-(N-Acylamino)-1,3-dienes for the Synthesis of Octahydroquinoline Derivatives
Fabrizio Lo Galbo; Ernesto G. Occhiato; Antonio Guarna; Cristina Faggi; Journal of Organic Chemistry 68 (2003) 6360–6368; doi:10.1021/jo0344687

data_4022474
_publ_section_title
;
 Preparation and Cycloaddition Reactions of Enantiopure
 2-(N-Acylamino)-1,3-dienes for the Synthesis of
 Octahydroquinoline Derivatives
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6360
_journal_page_last               6368
_journal_paper_doi               10.1021/jo0344687
_journal_volume                  68
_journal_year                    2003
_chemical_formula_sum            'C32 H34 N2 O2'
_chemical_formula_weight         478.61
_chemical_name_systematic
;
4aR,6R,7R-2-Oxo-7-phenyl-1-(R)-(1-phenyl-ethyl)-
1,2,3,4,4a,5,6,7-octahydro-quinoline-6-carboxylic
acid S-(1-phenyl-ethyl)-amide
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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(1)
_cell_angle_beta                 114.60(1)
_cell_angle_gamma                90.00(2)
_cell_formula_units_Z            2
_cell_length_a                   10.191(1)
_cell_length_b                   13.857(2)
_cell_length_c                   10.568(1)
_cell_measurement_reflns_used    20
_cell_measurement_temperature    293(2)
_cell_volume                     1356.9(3)
_computing_cell_refinement       'Siemens P4'
_computing_data_collection       'Siemens P4'
_computing_data_reduction        'Siemens P4'
_computing_molecular_graphics    Ortep3
_computing_publication_material  Ciftab
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Siemens P4'
_diffrn_measurement_method       'profile data from theta\2theta'
_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  0.0485
_diffrn_reflns_av_sigmaI/netI    0.0402
_diffrn_reflns_limit_h_max       1
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            2686
_diffrn_reflns_theta_full        60.00
_diffrn_reflns_theta_max         60.00
_diffrn_reflns_theta_min         4.60
_diffrn_standards_decay_%        50
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.568
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.171
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             512
_exptl_crystal_size_mid          0.6
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(5)
_refine_ls_extinction_coef       0.0040(14)
_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   0.705
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     355
_refine_ls_number_reflns         2289
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.705
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0547
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1975P)^2^+0.4088P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1581
_refine_ls_wR_factor_ref         0.1629
_reflns_number_gt                2153
_reflns_number_total             2289
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0344687si20030415_124803.cif
_cod_data_source_block           logalbo4-20b
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4022474