Synthetic studies on siphonariid polypropionates: synthesis and isomerization of the caloundrin B trioxaadamantane ring system.
Beye, Garrison E.; Goodman, Jonathan M.; Ward, Dale E.; Organic letters 11 (2009) 1373–1376; doi:10.1021/ol900192q

data_1503823
_publ_section_title
;
 Synthetic studies on siphonariid polypropionates: synthesis and
 isomerization of the caloundrin B trioxaadamantane ring system.
;
_journal_issue                   6
_journal_name_full               'Organic letters'
_journal_page_first              1373
_journal_page_last               1376
_journal_paper_doi               10.1021/ol900192q
_journal_volume                  11
_journal_year                    2009
_chemical_formula_moiety         'C14 H24 O4'
_chemical_formula_sum            'C14 H24 O4'
_chemical_formula_weight         256.33
_chemical_name_systematic
; (1R,3R,5R,7R,8S,9S,10R)-rel-3,5-Diethyl-8,9,10-
trimethyl-2,4,6-trioxatricyclo[3.3.1.13,7]decan-1-ol

;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 103.718(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.3198(4)
_cell_length_b                   12.4182(7)
_cell_length_c                   10.0138(5)
_cell_measurement_reflns_used    3205
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     1367.50(12)
_computing_cell_refinement       'HKL DENZO and SCALEPACK, Bruker AXS/Nonius'
_computing_data_collection       'COLLECT, Bruker AXS/Nonius'
_computing_data_reduction        'HKL DENZO and SCALEPACK, Bruker AXS/Nonius'
_computing_molecular_graphics
' Cameron (WinGX v1.70.01 2005), Ortep (SHELXTL-NT v6.14, Bruker AXS)'
_computing_publication_material  'WinGX v1.70.01 2005 (L. J. Farrugia)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution
' SIR-97 (A. Altomare, G. Cascarano, C. Giacovazzo et al., 1999)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type  'KappaCCD (BruKer AXS-Nonius, FR540C)'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_source         'Nonius FR590D, fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_sigmaI/netI    0.0450
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4856
_diffrn_reflns_theta_full        25.68
_diffrn_reflns_theta_max         25.68
_diffrn_reflns_theta_min         2.94
_diffrn_standards_decay_%        'no decay'
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.9823
_exptl_absorpt_correction_T_min  0.9780
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'HKL Scalepack (Otwinowski & Minor 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2593
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0641
_refine_ls_R_factor_gt           0.0419
_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^)+(0.0385P)^2^+0.4708P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0934
_refine_ls_wR_factor_ref         0.1050
_reflns_number_gt                1927
_reflns_number_total             2593
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol900192q_si_002.cif
_cod_data_source_block           14a
_cod_original_cell_volume        1367.50(11)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1503823