Unstabilized Azomethine Ylides for the Stereoselective Synthesis of Substituted Piperidines, Tropanes, and Azabicyclo[3.1.0] Systems
Michael A. Ischay; Michael K. Takase; Robert G. Bergman; Jonathan A. Ellman; Journal of the American Chemical Society 135 (2013) 2478–2481; doi:10.1021/ja312311k

data_4119367
_publ_section_title
;
 Unstabilized Azomethine Ylides for the Stereoselective Synthesis of
 Substituted Piperidines, Tropanes, and Azabicyclo[3.1.0] Systems
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2478
_journal_page_last               2481
_journal_paper_doi               10.1021/ja312311k
_journal_volume                  135
_journal_year                    2013
_chemical_formula_sum            'C27 H29 N O4'
_chemical_formula_weight         431.51
_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                68.476(5)
_cell_angle_beta                 88.094(6)
_cell_angle_gamma                89.144(6)
_cell_formula_units_Z            4
_cell_length_a                   7.9616(2)
_cell_length_b                   17.3191(4)
_cell_length_c                   17.5815(12)
_cell_measurement_reflns_used    26613
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      68.2
_cell_measurement_theta_min      2.7
_cell_volume                     2253.96(19)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r12 (Rigaku, 2011)'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r12 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r12 (Rigaku, 2011)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      93(2)
_diffrn_detector_area_resol_mean 22.2
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Rigaku Saturn 944+ CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'microfocus rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.1257
_diffrn_reflns_av_sigmaI/netI    0.0698
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            78513
_diffrn_reflns_theta_full        68.36
_diffrn_reflns_theta_max         68.36
_diffrn_reflns_theta_min         2.70
_exptl_absorpt_coefficient_mu    0.681
_exptl_absorpt_correction_T_max  0.9668
_exptl_absorpt_correction_T_min  0.9048
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private Communication'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_description       Needle
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.383
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     641
_refine_ls_number_reflns         8098
_refine_ls_number_restraints     226
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0787
_refine_ls_R_factor_gt           0.0684
_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^)+(0.0267P)^2^+5.9328P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1833
_refine_ls_wR_factor_ref         0.1884
_reflns_number_gt                6605
_reflns_number_total             8098
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja312311k_si_002.cif
_cod_data_source_block           12101
_cod_database_code               4119367