Oxidations of 3-alkenyltetronic acids with dimethyldioxirane (DMD) and air: regioselectivity and formation of a spirotricyclic hemiketal endoperoxide lactone
Schobert, Rainer; Siegfried, Sven; Weingärtner, Jochen; Nieuwenhuyzen, Mark; Journal of the Chemical Society, Perkin Transactions 1  (2001) 2009–; doi:10.1039/b104227k

data_7204972
_publ_section_title
;
 Oxidations of 3-alkenyltetronic acids with dimethyldioxirane (DMD) and
 air: regioselectivity and formation of a spirotricyclic hemiketal
 endoperoxide lactone
;
_journal_issue                   17
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 1'
_journal_page_first              2009
_journal_paper_doi               10.1039/b104227k
_journal_year                    2001
_chemical_formula_sum            'C14 H20 O5'
_chemical_formula_weight         268.30
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 114.824(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.456(2)
_cell_length_b                   8.9927(16)
_cell_length_c                   13.549(2)
_cell_measurement_temperature    153(2)
_cell_volume                     1377.4(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXTL (Sheldrick, 1998)'
_computing_structure_solution    'SHELXTL (Sheldrick, 1998)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.717
_diffrn_measured_fraction_theta_max 0.717
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       'Phi and 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  0.0835
_diffrn_reflns_av_sigmaI/netI    0.0447
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15084
_diffrn_reflns_theta_full        31.08
_diffrn_reflns_theta_max         31.08
_diffrn_reflns_theta_min         1.80
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.9789
_exptl_absorpt_correction_T_min  0.9547
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.452
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     252
_refine_ls_number_reflns         3171
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0601
_refine_ls_R_factor_gt           0.0481
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0944P)^2^+0.0321P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1288
_refine_ls_wR_factor_ref         0.1399
_reflns_number_gt                2516
_reflns_number_total             3171
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b104227k.txt
_cod_data_source_block           sieg1m
_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_cell_volume        1377.5(4)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7204972