Spiroketals via oxidative rearrangement of enol ethers.
Waller, David L.; Stephenson, Corey R. J.; Wipf, Peter; Organic & biomolecular chemistry 5 (2007) 58–60; doi:10.1039/b612992g

data_7151040
_publ_section_title
;
 Spiroketals via oxidative rearrangement of enol ethers.
;
_journal_issue                   1
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              58
_journal_page_last               60
_journal_paper_doi               10.1039/b612992g
_journal_volume                  5
_journal_year                    2007
_chemical_formula_sum            'C9 H12 O5'
_chemical_formula_weight         200.19
_chemical_melting_point          ?
_chemical_name_common
;
(1R*,3S*,6R*)-methyl-2,2-dimethyl-5-oxo-4,7-
dioxabicyclo(4.1.0) heptane-3-carboxylate
;
_chemical_name_systematic
;
(1R*,3S*,6R*)-methyl-2,2-dimethyl-5-oxo-4,7-dioxabicyclo[4.1.0]
heptane-3-carboxylate
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 104.129(18)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   25.345(17)
_cell_length_b                   6.038(4)
_cell_length_c                   12.627(10)
_cell_measurement_temperature    295(2)
_cell_volume                     1874(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker AXS Smart CCD'
_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  0.2741
_diffrn_reflns_av_sigmaI/netI    0.2339
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4776
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.66
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_max  0.9861
_exptl_absorpt_correction_T_min  0.9680
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXS Sadabs program'
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             848
_exptl_crystal_preparation       ethylacetate/hexanes
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.406
_refine_diff_density_min         -0.398
_refine_diff_density_rms         0.107
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.132
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     130
_refine_ls_number_reflns         1647
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.132
_refine_ls_R_factor_all          0.1859
_refine_ls_R_factor_gt           0.1225
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1045P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2742
_refine_ls_wR_factor_ref         0.3053
_reflns_number_gt                934
_reflns_number_total             1647
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b612992g.txt
_cod_data_source_block           compound9
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value 'nd' 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 
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_original_formula_sum        C9H12O5
_cod_database_code               7151040