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_4022473
_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            'C31 H28 N2 O3'
_chemical_formula_weight         476.55
_chemical_name_systematic
;
(3aR,4R,9aR,9bS)-2,4-Diphenyl-6-[(R)-1-phenyl-ethyl]-
4,6,8,9,9a,9b-hexahydro-3aH-pyrrolo[3,4-f]quinoline-1,3,7-trione
;
_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                90.000(2)
_cell_angle_beta                 90.139(2)
_cell_angle_gamma                90.000(2)
_cell_formula_units_Z            2
_cell_length_a                   8.986(1)
_cell_length_b                   9.522(1)
_cell_length_c                   14.420(1)
_cell_measurement_temperature    293(2)
_cell_volume                     1233.8(2)
_computing_cell_refinement       'SMART\Bruker CCD'
_computing_data_collection       'SMART\Bruker CCD'
_computing_data_reduction        'SMART\Bruker CCD'
_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 0.893
_diffrn_measured_fraction_theta_max 0.893
_diffrn_measurement_device_type  'Bruker CCD'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_monochromator  'crossed Gobels mirrors'
_diffrn_radiation_source         'rotating anod'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_av_sigmaI/netI    0.0431
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3684
_diffrn_reflns_theta_full        53.81
_diffrn_reflns_theta_max         53.81
_diffrn_reflns_theta_min         3.06
_exptl_absorpt_coefficient_mu    0.659
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             504
_exptl_crystal_size_mid          0.4
_refine_diff_density_max         0.131
_refine_diff_density_min         -0.146
_refine_diff_density_rms         0.036
_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       0.0022(7)
_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   0.852
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     331
_refine_ls_number_reflns         2239
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.852
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0460
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1084P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1138
_refine_ls_wR_factor_ref         0.1259
_reflns_number_gt                1791
_reflns_number_total             2239
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0344687si20030415_124728.cif
_cod_data_source_block           logalbo2-15c
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4022473