Enantiospecific synthesis of the cubitane skeleton.
Schöttner, Elisabeth; Wiechoczek, Maren; Jones, Peter G.; Lindel, Thomas; Organic letters 12 (2010) 784–787; doi:10.1021/ol902854t

data_1503418
_publ_section_title
;
 Enantiospecific synthesis of the cubitane skeleton.
;
_journal_issue                   4
_journal_name_full               'Organic letters'
_journal_page_first              784
_journal_page_last               787
_journal_paper_doi               10.1021/ol902854t
_journal_volume                  12
_journal_year                    2010
_chemical_formula_sum            'C21 H40 O3 Si'
_chemical_formula_weight         368.62
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.2696(3)
_cell_length_b                   12.6091(3)
_cell_length_c                   17.8108(5)
_cell_measurement_reflns_used    50568
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.7064
_cell_measurement_theta_min      3.5014
_cell_volume                     2306.33(11)
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.36 (release 29-09-2008 CrysAlis171 .NET)
(compiled Sep 29 2008,12:11:20)
;
_computing_data_collection
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.32.36 (release 29-09-2008 CrysAlis171 .NET)
(compiled Sep 29 2008,12:11:20)
;
_computing_data_reduction
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.36 (release 29-09-2008 CrysAlis171 .NET)
(compiled Sep 29 2008,12:11:20)
;
_computing_molecular_graphics    'Bruker Xp'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.3543
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Oxford Xcalibur Nova A'
_diffrn_measurement_method       \w-scans
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'Nova (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_sigmaI/netI    0.0104
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            54249
_diffrn_reflns_theta_full        67.50
_diffrn_reflns_theta_max         75.73
_diffrn_reflns_theta_min         4.30
_exptl_absorpt_coefficient_mu    1.005
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75599
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.36 (release 29-09-2008 CrysAlis171 .NET)
(compiled Sep 29 2008,12:11:20)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.062
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.016(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    'OH free, rigid methyls, others riding'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         4684
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0258
_refine_ls_R_factor_gt           0.0256
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0430P)^2^+0.3882P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0687
_refine_ls_wR_factor_ref         0.0688
_reflns_number_gt                4655
_reflns_number_total             4684
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol902854t_si_002.cif
_cod_data_source_block           eli
_cod_database_code               1503418
_chemical_absolute_congiguration ad