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_4113766
_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         'C12 H10 N2 O'
_chemical_formula_sum            'C12 H10 N2 O'
_chemical_formula_weight         198.220
_chemical_name_common            'N-benzoyliminopyridinium ylide'
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 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                   5.9959(1)
_cell_length_b                   8.5600(1)
_cell_length_c                   19.370(2)
_cell_measurement_reflns_used    9047
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.38
_cell_measurement_theta_min      2.28
_cell_volume                     994.16(10)
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1999)'
_computing_data_reduction        'SAINT (Bruker, 1999)'
_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_detector_area_resol_mean 5.5
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker AXS SMART 2K/Platform'
_diffrn_measurement_method       '\w scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus xray tube'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_sigmaI/netI    0.0228
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            11916
_diffrn_reflns_theta_full        72.47
_diffrn_reflns_theta_max         72.47
_diffrn_reflns_theta_min         4.57
_diffrn_standards_decay_%        0.0
_diffrn_standards_number         94
_exptl_absorpt_coefficient_mu    0.698
_exptl_absorpt_correction_T_max  0.9700
_exptl_absorpt_correction_T_min  0.9600
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.3243
_exptl_crystal_density_method    none
_exptl_crystal_description       block
_exptl_crystal_F_000             416.0
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.107
_refine_diff_density_min         -0.107
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details 'Flack (1983)'
_refine_ls_abs_structure_Flack   0.1(3)
_refine_ls_extinction_coef       0.0204(15)
_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   1.047
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         1961
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_restrained_S_obs      1.079
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0316
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0568P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0877
_refine_ls_wR_factor_ref         0.0861
_reflns_number_gt                1791
_reflns_number_total             1961
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            ja0348647si20030304_031113.cif
_cod_data_source_block           cmpd1
_cod_original_cell_volume        994.16(2)
_cod_database_code               4113766