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_4119010
_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_moiety         'C13 H18 Br N O2'
_chemical_formula_sum            'C13 H18 Br N O2'
_chemical_formula_weight         300.19
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_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                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   5.1753(9)
_cell_length_b                   8.4468(11)
_cell_length_c                   30.485(5)
_cell_measurement_reflns_used    8262
_cell_measurement_temperature    294
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      3.13
_cell_volume                     1332.6(4)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_diffrn_ambient_temperature      294
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0523
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            12954
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.084
_exptl_absorpt_correction_T_max  0.396
_exptl_absorpt_correction_T_min  0.192
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_description       chunk
_exptl_crystal_F_000             616.00
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.300
_refine_diff_density_max         0.470
_refine_diff_density_min         -0.700
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  1238 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.006(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     163
_refine_ls_number_reflns         3047
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0336
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0234P)^2^+0.5735P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0920
_reflns_number_gt                2173
_reflns_number_total             3047
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ja310249u_si_005.cif
_cod_data_source_block           511
_cod_database_code               4119010