Tandem Ring-Closing Metathesis Transannular Cyclization as a Route to Hydroxylated Pyrrolizidines. Asymmetric Synthesis of (+)-Australine
James D. White; Peter Hrnciar; Alexandre F. T. Yokochi; Journal of the American Chemical Society 120 (1998) 7359–7360; doi:10.1021/ja9811400

data_4116794
_publ_section_title
;
 Tandem Ring-Closing Metathesis Transannular Cyclization as a Route to
 Hydroxylated Pyrrolizidines. Asymmetric Synthesis of (+)-Australine
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7359
_journal_page_last               7360
_journal_paper_doi               10.1021/ja9811400
_journal_volume                  120
_journal_year                    1998
_chemical_formula_sum            'C23 H25 N O5'
_chemical_formula_weight         395.44
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_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                 91.683(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.7861(5)
_cell_length_b                   8.2071(3)
_cell_length_c                   19.3197(9)
_cell_measurement_reflns_used    94
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      34.92
_cell_measurement_theta_min      9.50
_cell_volume                     2026.47(14)
_computing_cell_refinement       'XSCANS V2.2'
_computing_data_collection       'XSCANS V2.2'
_computing_data_reduction        'XSCANS V2.2'
_computing_molecular_graphics    'XP V4.2'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       '\w/2\q scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_av_sigmaI/netI    0.0286
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            6002
_diffrn_reflns_theta_full        57.26
_diffrn_reflns_theta_max         57.26
_diffrn_reflns_theta_min         2.29
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.746
_exptl_absorpt_correction_T_max  0.9292
_exptl_absorpt_correction_T_min  0.7069
_exptl_absorpt_correction_type   Psi-scans
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_description       Plate
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_coef       0.00236(19)
_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   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     590
_refine_ls_number_reflns         5305
_refine_ls_number_restraints     228
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0418
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0552P)^2^+0.5654P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1061
_refine_ls_wR_factor_ref         0.1116
_reflns_number_gt                4817
_reflns_number_total             5305
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja9811400.cif
_cod_data_source_block           xl
_cod_depositor_comments
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The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0552P)^2^+0.5654P] 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^)+(0.0552P)^2^+0.5654P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
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_cod_database_code               4116794