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_7204254
_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         'C10 H17 N O'
_chemical_formula_sum            'C10 H17 N O'
_chemical_formula_weight         167.25
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   'constrained to idealised geometry'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   'Fourier difference syntheses'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 105.40(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.536(2)
_cell_length_b                   11.150(3)
_cell_length_c                   10.547(2)
_cell_measurement_reflns_used    40
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      24.5
_cell_measurement_theta_min      12
_cell_volume                     967.8(4)
_computing_cell_refinement       'STADI4 v1.07'
_computing_data_collection       'STADI4 v1.07 (Stoe, 1997)'
_computing_data_reduction        'XRED v1.09 (Stoe, 1996)'
_computing_molecular_graphics    'SHELXTL v5.03 (Sheldrick, 1994)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.947
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measurement_device       'Stoe Stadi-4 four-circle'
_diffrn_measurement_method       'omega-theta scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.092
_diffrn_reflns_av_sigmaI/netI    0.045
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            2067
_diffrn_reflns_theta_full        24.96
_diffrn_reflns_theta_max         24.96
_diffrn_reflns_theta_min         2.71
_diffrn_standards_decay_%        'random variation +/-3.2'
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.148
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       trapezoid
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.19
_refine_diff_density_min         -0.22
_refine_diff_density_rms         0.05
_refine_ls_extinction_coef       0.014(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    'all riding except hydroxyl (rotating)'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     111
_refine_ls_number_reflns         1702
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0827
_refine_ls_R_factor_gt           0.0570
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.042P)^2^+0.901P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1190
_refine_ls_wR_factor_ref         0.1407
_reflns_number_gt                1258
_reflns_number_total             1702
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b108182a.txt
_cod_data_source_block           alcohol-22
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.042P)^2^+0.901P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.042P)^2^+0.901P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 

The following automatic conversions were performed:

'_atom_sites_solution_primary' value 'direct methods' was changed to
'direct'.

Automatic conversion script
Id: cif_fix_values 6452 2018-10-05 10:23:21Z andrius 
;
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7204254