Regio- and stereoselective selenium dioxide allylic oxidation of (E)-dialkyl alkylidenesuccinates to (Z)-allylic alcohols: Synthesis of natural and unnatural butenolides.
Patel, Ramesh M.; Puranik, Vedavati G.; Argade, Narshinha P.; Organic & biomolecular chemistry 9 (2011) 6312–6322; doi:10.1039/c1ob05709j

data_7151972
_publ_section_title
;
 Regio- and stereoselective selenium dioxide allylic oxidation of
 (E)-dialkyl alkylidenesuccinates to (Z)-allylic alcohols: Synthesis of
 natural and unnatural butenolides.
;
_journal_issue                   18
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6312
_journal_page_last               6322
_journal_paper_doi               10.1039/c1ob05709j
_journal_volume                  9
_journal_year                    2011
_chemical_formula_moiety         'C7 H8 O4'
_chemical_formula_sum            'C7 H8 O4'
_chemical_formula_weight         156.13
_chemical_melting_point          404.1(10)
_chemical_name_common            Butenolides
_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                 98.1180(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.0397(3)
_cell_length_b                   14.3513(10)
_cell_length_c                   10.3160(7)
_cell_measurement_reflns_used    3185
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.136
_cell_measurement_theta_min      2.447
_cell_volume                     738.64(8)
_computing_cell_refinement       'BRUKER SAINT'
_computing_data_collection       'BRUKER SMART'
_computing_data_reduction        'BRUKER SAINT'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       ' Bruker Smart APEX'
_diffrn_measurement_device_type  ' CCD Area Detector'
_diffrn_measurement_method       'Omega Scan'
_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  0.0217
_diffrn_reflns_av_sigmaI/netI    0.0137
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6969
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.45
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_max  0.9983
_exptl_absorpt_correction_T_min  0.9910
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.503
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     102
_refine_ls_number_reflns         1291
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.110
_refine_ls_R_factor_all          0.0678
_refine_ls_R_factor_gt           0.0658
_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^)+(0.0726P)^2^+0.6566P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1684
_refine_ls_wR_factor_ref         0.1702
_reflns_number_gt                1233
_reflns_number_total             1291
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1ob05709j.txt
_cod_data_source_block           C7H8O4compound8
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '130-132 degree Centigrade' was
changed to '404.1(10)' - it was converted from degrees Celsius(C) to
Kelvins(K), the average value was taken and precision was
estimated.

'_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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7151972