Diverging Pathways to Topologically Complex Polycyclic Bis-acetals and Their Ring System Interchange.
Castillo, Rafael R.; Aquino, Maurizio; Gandara, Zoila; Safir, Imad; Elkhayat, Zobida; Retailleau, Pascal; Arseniyadis, Siméon; Organic letters 14 (2012) 1628–1631; doi:10.1021/ol300388b

data_1507202
_publ_section_title
;
 Diverging Pathways to Topologically Complex Polycyclic Bis-acetals and
 Their Ring System Interchange.
;
_journal_issue                   6
_journal_name_full               'Organic letters'
_journal_page_first              1628
_journal_page_last               1631
_journal_paper_doi               10.1021/ol300388b
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C20 H26 O6'
_chemical_formula_sum            'C20 H26 O6'
_chemical_formula_weight         362.41
_chemical_name_systematic
;racemic 
((2S,2aS,6aS,8S,12bR)-9,10,11-trimethoxy-2,3,4,5,6,7,8,12b-octahydro-2a,8
-epoxynaphtho[1,2-c]isobenzofuran-2-yl)methanol  
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                92.296(7)
_cell_angle_beta                 90.564(6)
_cell_angle_gamma                98.526(7)
_cell_formula_units_Z            2
_cell_length_a                   8.1543(3)
_cell_length_b                   10.2746(3)
_cell_length_c                   10.7365(7)
_cell_measurement_reflns_used    5098
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      68.2
_cell_measurement_theta_min      6.8
_cell_volume                     888.76(7)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement
'SHELXL97 (Sheldrick, 2008); CRYSTALBUILDER (Welter, 2006)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_type
'RAPID II large area curved imaging plate detector '
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_details
;
scan:
    Number of images: 36
               Slice: 20.0000 - 200.0000
         Image width: 5.0000
            Exp time: 210.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 0.0000
                 Phi: 0.0000
                 XTD: 127.4000
              2theta: 0.0000
scan:
    Number of images: 26
               Slice: 20.0000 - 153.0000
         Image width: 5.0000
            Exp time: 210.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 54.0000
                 Phi: 0.0000
                 XTD: 127.4000
              2theta: 0.0000
scan:
    Number of images: 20
               Slice: 20.0000 - 124.0000
         Image width: 5.0000
            Exp time: 210.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 54.0000
                 Phi: 270.0000
                 XTD: 127.4000
              2theta: 0.0000
scan:
    Number of images: 20
               Slice: 42.0000 - 144.0000
         Image width: 5.0000
            Exp time: 210.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 54.0000
                 Phi: 90.0000
                 XTD: 127.4000
              2theta: 0.0000
scan:
    Number of images: 11
               Slice: 42.0000 - 97.0000
         Image width: 5.0000
            Exp time: 210.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 54.0000
                 Phi: 180.0000
                 XTD: 127.4000
              2theta: 0.0000
scan:
    Number of images: 32
               Slice: 24.0000 - 184.0000
         Image width: 5.0000
            Exp time: 210.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 30.0000
                 Phi: 180.0000
                 XTD: 127.4000
              2theta: 0.0000
scan:
    Number of images: 20
               Slice: 60.0000 - 160.0000
         Image width: 5.0000
            Exp time: 210.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 15.0000
                 Phi: 0.0000
                 XTD: 127.4000
              2theta: 0.0000
scan:
    Number of images: 22
               Slice: 90.0000 - 200.0000
         Image width: 5.0000
            Exp time: 210.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 45.0000
                 XTD: 127.4000
              2theta: 0.0000

;
_diffrn_measurement_device_type  'Rigaku rapid II RAXIS conversion'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_orient_matrix_type       FS_PROCESS
_diffrn_orient_matrix_UB_11      -0.006234
_diffrn_orient_matrix_UB_12      -0.070202
_diffrn_orient_matrix_UB_13      0.062386
_diffrn_orient_matrix_UB_21      -0.091921
_diffrn_orient_matrix_UB_22      0.037441
_diffrn_orient_matrix_UB_23      0.042895
_diffrn_orient_matrix_UB_31      -0.083023
_diffrn_orient_matrix_UB_32      -0.058073
_diffrn_orient_matrix_UB_33      -0.054400
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0475
_diffrn_reflns_av_sigmaI/netI    0.0392
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10868
_diffrn_reflns_theta_full        68.25
_diffrn_reflns_theta_max         68.25
_diffrn_reflns_theta_min         6.82
_exptl_absorpt_coefficient_mu    0.819
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.834
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'thick plate'
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         3141
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0525
_refine_ls_R_factor_gt           0.0443
_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^)+(0.0696P)^2^+0.3126P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1181
_refine_ls_wR_factor_ref         0.1368
_reflns_number_gt                2644
_reflns_number_total             3141
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol300388b_si_003.cif
_cod_data_source_block           compound_8d
_cod_database_code               1507202