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_1503822
_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 H20 O4 S2'
_chemical_formula_sum            'C14 H20 O4 S2'
_chemical_formula_weight         316.42
_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
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.6297(5)
_cell_length_b                   10.2315(4)
_cell_length_c                   16.3301(9)
_cell_measurement_reflns_used    1914
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.88
_cell_measurement_theta_min      1.00
_cell_volume                     1441.86(13)
_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 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0474
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            3397
_diffrn_reflns_theta_full        27.85
_diffrn_reflns_theta_max         27.85
_diffrn_reflns_theta_min         3.19
_diffrn_standards_decay_%        'no decay'
_exptl_absorpt_coefficient_mu    0.379
_exptl_absorpt_correction_T_max  0.9280
_exptl_absorpt_correction_T_min  0.9111
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'HKL Scalepack (Otwinowski & Minor 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881; 1329 Friedel pairs '
_refine_ls_abs_structure_Flack   -0.04(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         3397
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0585
_refine_ls_R_factor_gt           0.0446
_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^)+(0.0096P)^2^+1.2055P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0831
_refine_ls_wR_factor_ref         0.0921
_reflns_number_gt                2949
_reflns_number_total             3397
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol900192q_si_002.cif
_cod_data_source_block           30
_cod_database_code               1503822