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_4119369
_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            'C21 H26 Cl N'
_chemical_formula_weight         327.88
_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                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   22.7381(16)
_cell_length_b                   14.1039(3)
_cell_length_c                   11.6051(2)
_cell_measurement_reflns_used    43292
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.5
_cell_measurement_theta_min      3.0
_cell_volume                     3721.7(3)
_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      150(2)
_diffrn_detector_area_resol_mean 10
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID imaging plate'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0492
_diffrn_reflns_av_sigmaI/netI    0.0220
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            71180
_diffrn_reflns_theta_full        30.51
_diffrn_reflns_theta_max         30.51
_diffrn_reflns_theta_min         3.38
_exptl_absorpt_coefficient_mu    0.205
_exptl_absorpt_correction_T_max  0.9798
_exptl_absorpt_correction_T_min  0.9505
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private Communication'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.170
_exptl_crystal_description       Block
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.383
_refine_diff_density_min         -0.430
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         5684
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0450
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0476P)^2^+0.9949P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1078
_refine_ls_wR_factor_ref         0.1150
_reflns_number_gt                4354
_reflns_number_total             5684
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja312311k_si_004.cif
_cod_data_source_block           s12093
_cod_database_code               4119369