A photocycloaddition/fragmentation approach toward the 3,12-dioxatricyclo[8.2.1.0(6,13)]tridecane skeleton of terpenoid natural products.
Hehn, Jörg P; Herdtweck, Eberhardt; Bach, Thorsten; Organic letters 13 (2011) 1892–1895; doi:10.1021/ol2004462

data_1502101
_publ_section_title
;
 A photocycloaddition/fragmentation approach toward the
 3,12-dioxatricyclo[8.2.1.0(6,13)]tridecane skeleton of terpenoid natural
 products.
;
_journal_issue                   7
_journal_name_full               'Organic letters'
_journal_page_first              1892
_journal_page_last               1895
_journal_paper_doi               10.1021/ol2004462
_journal_volume                  13
_journal_year                    2011
_chemical_formula_moiety         'C15 H20 O5'
_chemical_formula_sum            'C15 H20 O5'
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_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                88.568(2)
_cell_angle_beta                 78.057(2)
_cell_angle_gamma                70.267(2)
_cell_formula_units_Z            2
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_cell_length_b                   8.6083(4)
_cell_length_c                   13.4229(6)
_cell_measurement_reflns_used    9817
_cell_measurement_temperature    173(1)
_cell_measurement_theta_max      25.37
_cell_measurement_theta_min      1.55
_cell_volume                     694.45(6)
_computing_cell_refinement       'SAINT (Bruker, 2008b)'
_computing_data_collection       'APEX II Control Software (Bruker, 2008a)'
_computing_data_reduction        'SAINT (Bruker, 2008b)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1998)'
_computing_structure_solution    'SIR92 (Altomare, 1994)'
_diffrn_ambient_temperature      173(1)
_diffrn_detector                 ' CCD plate '
_diffrn_detector_area_resol_mean 16
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device       ' \k-geometry diffractometer '
_diffrn_measurement_device_type  ' Bruker APEX-II CCD '
_diffrn_measurement_method       ' phi- and omega-rotation '
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode FR591'
_diffrn_radiation_type           'Mo K\a'
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_diffrn_reflns_av_R_equivalents  0.0306
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_diffrn_reflns_limit_h_max       7
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_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
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_diffrn_reflns_theta_max         25.37
_diffrn_reflns_theta_min         1.55
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6747
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_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_density_method    none
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_exptl_crystal_size_min          0.36
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_refine_diff_density_min         -0.234
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_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     261
_refine_ls_number_reflns         2457
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0368
_refine_ls_R_factor_gt           0.0358
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0353P)^2^+0.3464P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_gt          0.0863
_refine_ls_wR_factor_ref         0.0872
_reflns_number_gt                2373
_reflns_number_total             2457
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ol2004462_si_002.cif
_cod_data_source_block           compound_6
_cod_database_code               1502101