Complexation Promoted Additions to N-Benzoyliminopyridinium Ylides. A Novel and Highly Regioselective Approach to Polysubstituted Piperidines
Claude Legault; André B. Charette; Journal of the American Chemical Society 125 (2003) 6360–6361; doi:10.1021/ja0348647

data_4113767
_publ_section_title
;
 Complexation Promoted Additions to N-Benzoyliminopyridinium Ylides. A
 Novel and Highly Regioselective Approach to Polysubstituted Piperidines
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6360
_journal_page_last               6361
_journal_paper_doi               10.1021/ja0348647
_journal_volume                  125
_journal_year                    2003
_chemical_formula_moiety         'C16 H22 N2 O'
_chemical_formula_sum            'C16 H22 N2 O'
_chemical_formula_weight         258.356
_chemical_name_common            'compound 2e'
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'SHELXL96 (Sheldrick, 1996)'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.849(3)
_cell_length_b                   17.062(15)
_cell_length_c                   9.952(8)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.00
_cell_measurement_theta_min      10.00
_cell_volume                     1502.6(19)
_computing_cell_refinement       'CAD-4 software (Enraf-Nonius, 1989)'
_computing_data_collection       'CAD-4 software (Enraf-Nonius, 1989)'
_computing_data_reduction        'NRC-2, NRC-2A (Ahmed et al, 1973)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  'SHELXL96 (Sheldrick, 1996)'
_computing_structure_refinement  'SHELXL96 (Sheldrick, 1996)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device_type  'Nonius CAD-4'
_diffrn_measurement_method       '\w scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus xray tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54056
_diffrn_reflns_av_R_equivalents  0.136
_diffrn_reflns_av_sigmaI/netI    0.0668
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            13242
_diffrn_reflns_theta_max         69.85
_diffrn_reflns_theta_min         2.59
_diffrn_standards_decay_%        6.1
_diffrn_standards_interval_time  60
_diffrn_standards_number         5
_exptl_absorpt_coefficient_mu    0.560
_exptl_absorpt_correction_T_max  0.9487
_exptl_absorpt_correction_T_min  0.7775
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'ABSORP in NRCVAX (Gabe et al, 1989)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.1421
_exptl_crystal_density_method    none
_exptl_crystal_description       block
_exptl_crystal_F_000             560.0
_exptl_crystal_size_max          0.68
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 'Flack (1983)'
_refine_ls_abs_structure_Flack   -0.7(8)
_refine_ls_extinction_coef       0.0030(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL96 (Sheldrick, 1996)'
_refine_ls_goodness_of_fit_all   0.953
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2853
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.952
_refine_ls_restrained_S_obs      1.105
_refine_ls_R_factor_all          0.1144
_refine_ls_R_factor_gt           0.0977
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1479P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.2399
_refine_ls_wR_factor_ref         0.2242
_reflns_number_gt                1864
_reflns_number_total             2853
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            ja0348647si20030304_031131.cif
_cod_data_source_block           cmpd2e
_cod_database_code               4113767