Stereoselective synthesis of donor-acceptor substituted cyclopropafuranones by intramolecular cyclopropanation of vinylogous carbonates: divergent synthesis of tetrahydrofuran-3-one, tetrahydropyran-3-one, and lactones.
Gharpure, Santosh J.; Shukla, Manoj K.; Vijayasree, U.; Organic letters 11 (2009) 5466–5469; doi:10.1021/ol902301h

data_1504287
_publ_section_title
;
 Stereoselective synthesis of donor-acceptor substituted
 cyclopropafuranones by intramolecular cyclopropanation of vinylogous
 carbonates: divergent synthesis of tetrahydrofuran-3-one,
 tetrahydropyran-3-one, and lactones.
;
_journal_issue                   23
_journal_name_full               'Organic letters'
_journal_page_first              5466
_journal_page_last               5469
_journal_paper_doi               10.1021/ol902301h
_journal_volume                  11
_journal_year                    2009
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C7 H8 O4'
_chemical_formula_sum            'C7 H8 O4'
_chemical_formula_weight         156.13
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
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_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.1758(4)
_cell_length_b                   9.0571(8)
_cell_length_c                   12.9827(10)
_cell_measurement_reflns_used    778
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      20.85
_cell_measurement_theta_min      2.74
_cell_volume                     726.19(10)
_computing_cell_refinement       'APEX II,Bruker,2004'
_computing_data_collection       'APEX II,Bruker,2004'
_computing_data_reduction        SAINT,Bruker,2004
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.918
_diffrn_measurement_device_type  'Bruker Apex II CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
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_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4917
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.25
_diffrn_reflns_theta_min         2.74
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_T_max  0.9778
_exptl_absorpt_correction_T_min  0.9596
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 1999)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.35
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_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.123
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_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1(2)
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_refine_ls_matrix_type           full
_refine_ls_number_parameters     113
_refine_ls_number_reflns         1534
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.838
_refine_ls_R_factor_all          0.0988
_refine_ls_R_factor_gt           0.0472
_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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1155
_refine_ls_wR_factor_ref         0.1480
_reflns_number_gt                917
_reflns_number_total             1534
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol902301h_si_003.cif
_cod_data_source_block           new
_cod_depositor_comments
;
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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               1504287