Divergent Synthesis and Chemical Reactivity of Bicyclic Lactone Fragments of Complex Rearranged Spongian Diterpenes
Martin J. Schnermann; Christopher M. Beaudry; Nathan E. Genung; Stephen M. Canham; Nicholas L. Untiedt; Breanne D. W. Karanikolas; Christine Sütterlin; Larry E. Overman; Journal of the American Chemical Society 133 (2011) 17494–17503; doi:10.1021/ja207727h

data_4107035
_publ_section_title
;
 Divergent Synthesis and Chemical Reactivity of Bicyclic Lactone Fragments
 of Complex Rearranged Spongian Diterpenes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              17494
_journal_page_last               17503
_journal_paper_doi               10.1021/ja207727h
_journal_volume                  133
_journal_year                    2011
_chemical_absolute_configuration syn
_chemical_formula_sum            'C12 H18 O5'
_chemical_formula_weight         242.26
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXTL
_cell_angle_alpha                90.00
_cell_angle_beta                 93.7230(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.0994(7)
_cell_length_b                   13.1141(9)
_cell_length_c                   18.8097(13)
_cell_measurement_reflns_used    9976
_cell_measurement_temperature    143(2)
_cell_measurement_theta_max      26.15
_cell_measurement_theta_min      2.23
_cell_volume                     2486.0(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      143(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w 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  0.0297
_diffrn_reflns_av_sigmaI/netI    0.0368
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            26943
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.41
_diffrn_reflns_theta_min         1.89
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.9776
_exptl_absorpt_correction_T_min  0.9743
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_density_meas      ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     629
_refine_ls_number_reflns         10179
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0380
_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^)+(0.0471P)^2^+0.2853P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0865
_refine_ls_wR_factor_ref         0.0904
_reflns_number_gt                8998
_reflns_number_total             10179
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja207727h_si_001.cif
_cod_data_source_block           leo238
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_database_code               4107035