Total Synthesis of Gelsemoxonine through a Spirocyclopropane Isoxazolidine Ring Contraction.
Diethelm, Stefan; Carreira, Erick M.; Journal of the American Chemical Society 137 (2015) 6084–6096; doi:10.1021/jacs.5b02574

data_4123793
_publ_section_title
;
 Total Synthesis of Gelsemoxonine through a Spirocyclopropane
 Isoxazolidine Ring Contraction.
;
_journal_issue                   18
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6084
_journal_page_last               6096
_journal_paper_doi               10.1021/jacs.5b02574
_journal_volume                  137
_journal_year                    2015
_chemical_formula_sum            'C14 H19 N O5'
_chemical_formula_weight         281.30
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                99.622(3)
_cell_angle_beta                 116.183(3)
_cell_angle_gamma                97.613(3)
_cell_formula_units_Z            2
_cell_length_a                   9.1457(7)
_cell_length_b                   9.4389(9)
_cell_length_c                   9.6930(8)
_cell_measurement_reflns_used    2465
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      2.42
_cell_volume                     719.94(11)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Platon, Ortep'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement
'OLEX2 (Dolomanov, 2009), SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
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_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6637
_diffrn_reflns_theta_full        27.62
_diffrn_reflns_theta_max         27.62
_diffrn_reflns_theta_min         2.25
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.9844
_exptl_absorpt_correction_T_min  0.9767
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.753
_refine_diff_density_min         -0.253
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_refine_ls_extinction_method     none
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_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         3311
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.967
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0430
_refine_ls_shift/su_max          0.015
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0740P)^2^+0.2728P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1134
_refine_ls_wR_factor_ref         0.1259
_reflns_number_gt                2704
_reflns_number_total             3311
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja5b02574_si_004.cif
_cod_data_source_block           ca160611_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 
;
_cod_original_cell_volume        719.93(11)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4123793