Rearrangement of ammonium ylides produced by intramolecular reaction of catalytically generated metal carbenoids. Part 2. Stereoselective synthesis of bicyclic amines
J. Stephen Clark; Paul B. Hodgson; Michael D. Goldsmith; Alexander J. Blake; Paul A. Cooke; Leslie J. Street; J. Chem. Soc., Perkin Trans. 1  (2001) 3325–3337; doi:10.1039/b108182a

data_7204255
_publ_section_title
;
 Rearrangement of ammonium ylides produced by intramolecular reaction
 of catalytically generated metal carbenoids. Part 2. Stereoselective
 synthesis of bicyclic amines
;
_journal_issue                   24
_journal_name_full               'J. Chem. Soc., Perkin Trans. 1'
_journal_page_first              3325
_journal_page_last               3337
_journal_paper_doi               10.1039/b108182a
_journal_year                    2001
_chemical_formula_moiety         'C11 H19 N O'
_chemical_formula_sum            'C11 H19 N O'
_chemical_formula_weight         181.27
_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
'OH from difference Fourier synthesis, others placed geometrically'
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.996(2)
_cell_length_b                   8.413(3)
_cell_length_c                   6.982(2)
_cell_measurement_temperature    293(2)
_cell_volume                     1115.8(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Siemens P4RA'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.064
_diffrn_reflns_av_sigmaI/netI    0.059
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1373
_diffrn_reflns_theta_full        50.35
_diffrn_reflns_theta_max         50.35
_diffrn_reflns_theta_min         4.66
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.530
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.079
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tablet
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.19
_refine_diff_density_min         -0.14
_refine_diff_density_rms         0.03
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   'not reliably determined'
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    'rigid group and riding model, respectively'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     116
_refine_ls_number_reflns         637
_refine_ls_number_restraints     35
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0541
_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^)+(0.075P)^2^+0.046P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1345
_refine_ls_wR_factor_ref         0.1410
_reflns_number_gt                543
_reflns_number_total             637
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b108182a.txt
_cod_data_source_block           alcohol-23
_cod_original_sg_symbol_H-M      Pca21
_cod_database_code               7204255