Concise Substrate-Controlled Asymmetric Total Syntheses of Dioxabicyclic Marine Natural Products with 2,10-Dioxabicyclo-[7.3.0]dodecene and 2,9-Dioxabicyclo[6.3.0]undecene Skeletons
Mi Jung Kim; Te-ik Sohn; Deukjoon Kim; Robert S. Paton; Journal of the American Chemical Society 134 (2012) 20178–20188; doi:10.1021/ja310249u

data_4119009
_publ_section_title
;
 Concise Substrate-Controlled Asymmetric Total Syntheses of Dioxabicyclic
 Marine Natural Products with 2,10-Dioxabicyclo-[7.3.0]dodecene and
 2,9-Dioxabicyclo[6.3.0]undecene Skeletons
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              20178
_journal_page_last               20188
_journal_paper_doi               10.1021/ja310249u
_journal_volume                  134
_journal_year                    2012
_chemical_formula_sum            'C15 H21 Br O3'
_chemical_formula_weight         329.23
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 111.124(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.4767(3)
_cell_length_b                   4.7717(1)
_cell_length_c                   20.1538(4)
_cell_measurement_reflns_used    3534
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      25.49
_cell_measurement_theta_min      2.48
_cell_volume                     1478.05(5)
_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      100(1)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_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  0.0421
_diffrn_reflns_av_sigmaI/netI    0.0795
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            14308
_diffrn_reflns_theta_full        28.38
_diffrn_reflns_theta_max         28.38
_diffrn_reflns_theta_min         2.48
_exptl_absorpt_coefficient_mu    2.783
_exptl_absorpt_correction_T_max  0.9464
_exptl_absorpt_correction_T_min  0.6060
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            silver
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_density_meas      ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.785
_refine_diff_density_min         -0.663
_refine_diff_density_rms         0.089
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.011(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.966
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         6668
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.966
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0368
_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^)+(0.0122P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0662
_refine_ls_wR_factor_ref         0.0709
_reflns_number_gt                5565
_reflns_number_total             6668
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja310249u_si_004.cif
_cod_data_source_block           20120516lt_0m
_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               4119009