Efficient Synthesis of Enantiopure Pyrrolizidinone Amino Acid
Evelyne Dietrich; William D. Lubell; Journal of Organic Chemistry 68 (2003) 6988–6996; doi:10.1021/jo034739d

data_4022511
_publ_contact_author
;
    Dr William D. Lubell
    Departement de Chimie
    Universite de Montreal
    C.P. 6128, Succ. Centre-ville
    Montreal, Quebec
    Canada H3C 3J7
;
_publ_contact_author_email       lubell@chimie.umontreal.ca
_publ_contact_author_fax         '514 343 7586'
_publ_contact_author_phone       '514 343 7339'
_publ_section_title
;
 Efficient Synthesis of Enantiopure Pyrrolizidinone Amino Acid
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6988
_journal_page_last               6996
_journal_paper_doi               10.1021/jo034739d
_journal_volume                  68
_journal_year                    2003
_chemical_compound_source        'synthesized by the authors, see text'
_chemical_formula_moiety         'C14 H22 N2 O5'
_chemical_formula_sum            'C14 H22 N2 O5'
_chemical_formula_weight         298.336
_chemical_name_common
;
(3S,5R,8S)-methyl 3-[N-(Boc)]
amino-1-azabicyclo[3.3.0]octan-2-one 8-carboxylate
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_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                 124.96(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.601(13)
_cell_length_b                   6.823(2)
_cell_length_c                   15.622(7)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.00
_cell_measurement_theta_min      20.00
_cell_volume                     1624.9(14)
_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  0.037
_diffrn_reflns_av_sigmaI/netI    0.0405
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            31265
_diffrn_reflns_theta_max         69.77
_diffrn_reflns_theta_min         3.45
_diffrn_standards_decay_%        4.6
_diffrn_standards_interval_time  60
_diffrn_standards_number         5
_exptl_absorpt_coefficient_mu    0.773
_exptl_absorpt_correction_T_max  0.9102
_exptl_absorpt_correction_T_min  0.7739
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'ABSORP in NRCVAX (Gabe et al, 1989)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.2195
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       block
_exptl_crystal_F_000             640.0
_exptl_crystal_size_max          0.57
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.098
_refine_diff_density_min         -0.118
_refine_diff_density_rms         0.026
_refine_ls_abs_structure_details 'Flack (1983)'
_refine_ls_abs_structure_Flack   0.3(3)
_refine_ls_extinction_coef       0.0038(3)
_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   0.847
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         3051
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.847
_refine_ls_restrained_S_obs      1.007
_refine_ls_R_factor_all          0.0594
_refine_ls_R_factor_gt           0.0472
_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^)+(0.0671P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1134
_refine_ls_wR_factor_ref         0.1091
_reflns_number_gt                2052
_reflns_number_total             3051
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            jo034739dsi20030530_034925.cif
_cod_data_source_block           lube24
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               4022511