Asymmetric Synthesis, Structure, and Reactivity of Unexpectedly Stable Spiroepoxy-β-Lactones Including Facile Conversion to Tetronic Acids: Application to (+)-Maculalactone A
Richard J. Duffy; Kay A. Morris; Ravikrishna Vallakati; Wei Zhang; Daniel Romo; Journal of Organic Chemistry 74 (2009) 4772–4781; doi:10.1021/jo900499e

data_4024627
_publ_section_title
;
Asymmetric Synthesis, Structure, and Reactivity of Unexpectedly Stable
Spiroepoxy-\b-Lactones Including Facile Conversion to Tetronic Acids:
Application to (+)-Maculalactone A
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4772
_journal_page_last               4781
_journal_paper_doi               10.1021/jo900499e
_journal_volume                  74
_journal_year                    2009
_chemical_absolute_configuration ab
_chemical_formula_sum            'C19 H15 F3 O5 S'
_chemical_formula_weight         412.37
_space_group_IT_number           19
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_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
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_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.0114(8)
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_cell_length_c                   34.767(3)
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_cell_volume                     1826.6(3)
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_collection       'Bruker FRAMBO'
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_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      100(2)
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_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'MWPC area detector'
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_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0000
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_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
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_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            20057
_diffrn_reflns_theta_full        58.93
_diffrn_reflns_theta_max         58.93
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_exptl_absorpt_coefficient_mu    2.125
_exptl_absorpt_correction_T_max  0.9791
_exptl_absorpt_correction_T_min  0.6760
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             848
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_refine_diff_density_max         0.176
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_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.003(9)
_refine_ls_extinction_method     none
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_refine_ls_number_parameters     313
_refine_ls_number_reflns         20057
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0356
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_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0256P)^2^+0.2150P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0802
_refine_ls_wR_factor_ref         0.0847
_reflns_Friedel_coverage         12%
_reflns_number_gt                18178
_reflns_number_total             20057
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo900499e_si_003.cif
_cod_data_source_block           dr37
_cod_depositor_comments
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The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
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 
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_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               4024627