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_7151041
_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            'C10 H16 O5'
_chemical_formula_weight         216.23
_chemical_melting_point          115.4(9)
_chemical_name_common
;
(1R*,3S*,5S*,6R*)-methyl-5-hydroxy-2,2,5-trimethyl-4,7-
dioxabicyclo(4.1.0)heptane-3-carboxylate
;
_chemical_name_systematic
;
(1R*,3S*,5S*,6R*)-methyl-5-hydroxy-2,2,5-trimethyl-4,7-
dioxabicyclo[4.1.0]heptane-3-carboxylate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 101.154(19)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.849(2)
_cell_length_b                   15.512(3)
_cell_length_c                   8.0902(17)
_cell_measurement_temperature    208(2)
_cell_volume                     1089.5(4)
_computing_cell_refinement       'Siemens P3/PC'
_computing_data_collection       'Siemens P3/PC'
_computing_data_reduction        'Siemens P3/PC'
_computing_molecular_graphics    'Siemens XP'
_computing_publication_material  'Siemens XP'
_diffrn_ambient_temperature      208(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Siemens P3'
_diffrn_measurement_method       'omega scans'
_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  0.0245
_diffrn_reflns_av_sigmaI/netI    0.0512
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -3
_diffrn_reflns_number            2284
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.35
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             464
_exptl_crystal_preparation       ethylacetate/hexanes
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2132
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0959
_refine_ls_R_factor_gt           0.0567
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0554P)^2^+0.8218P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1245
_refine_ls_wR_factor_ref         0.1445
_reflns_number_gt                1408
_reflns_number_total             2132
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b612992g.txt
_cod_data_source_block           compound15
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '114.5-116.3' was changed to
'115.4(9)' - the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_original_formula_sum        C10H16O5
_cod_database_code               7151041