Synthesis of Enantiopure Indolizinones by Cascade Ring Enlargements of 4'-Chlorospiro[cyclopropane-1,5'-isoxazolidines]
Julia Revuelta; Stefano Cicchi; Cristina Faggi; Sergei I. Kozhushkov; Armin de Meijere; Alberto Brandi; Journal of Organic Chemistry 71 (2006) 2417–2423; doi:10.1021/jo052564x

data_4021572
_publ_section_title
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 Synthesis of Enantiopure Indolizinones by Cascade Ring
 Enlargements of 4'-Chlorospiro[cyclopropane-1,5'-isoxazolidines]
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_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2417
_journal_page_last               2423
_journal_paper_doi               10.1021/jo052564x
_journal_volume                  71
_journal_year                    2006
_chemical_formula_sum            'C14 H22 Cl N O4'
_chemical_formula_weight         303.78
_chemical_melting_point          ?
_chemical_name_systematic
;
 Methyl (2aS,7S,7aR,7bR)-7-tert-Butoxy-2a-chlorohexahydro
 cyclobuta[d]pyrrolo[1,2-b]isoxazole-7b-(1H)-carboxylate 
;
_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
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.pre23_10 beta (release 21.06.2004 CrysAlis171 .NET)
(compiled Jun 21 2004,12:00:08)
;
_cell_angle_alpha                90.000(10)
_cell_angle_beta                 90.000(9)
_cell_angle_gamma                90.000(10)
_cell_formula_units_Z            4
_cell_length_a                   7.9490(10)
_cell_length_b                   10.221(2)
_cell_length_c                   19.480(2)
_cell_measurement_temperature    293(2)
_cell_volume                     1582.7(4)
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.'
_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd.'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.'
_computing_molecular_graphics    Ortep3
_computing_publication_material  Ciftab
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_method       'profile data from omega scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-Ray source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1008
_diffrn_reflns_av_sigmaI/netI    0.0699
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            13228
_diffrn_reflns_theta_full        23.27
_diffrn_reflns_theta_max         23.27
_diffrn_reflns_theta_min         4.05
_exptl_absorpt_coefficient_mu    0.253
_exptl_absorpt_correction_type   sadabs
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(16)
_refine_ls_extinction_coef       0.012(6)
_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   1.005
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2255
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.0939
_refine_ls_R_factor_gt           0.0646
_refine_ls_shift/su_max          0.218
_refine_ls_shift/su_mean         0.035
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0951P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1530
_refine_ls_wR_factor_ref         0.1724
_reflns_number_gt                1626
_reflns_number_total             2255
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo052564xsi20051213_083402.cif
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value 'not measured' was changed to '?' -
the value is undefined or not given.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
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_cod_database_code               4021572