A General Strategy for the Stereocontrolled Preparation of Diverse 8- and 9-Membered Laurencia-Type Bromoethers
Scott A. Snyder; Daniel S. Treitler; Alexandria P. Brucks; Wesley Sattler; Journal of the American Chemical Society 133 (2011) 15898–15901; doi:10.1021/ja2069449

data_4106935
_publ_section_title
;
 A General Strategy for the Stereocontrolled Preparation of Diverse 8- and
 9-Membered Laurencia-Type Bromoethers
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15898
_journal_page_last               15901
_journal_paper_doi               10.1021/ja2069449
_journal_volume                  133
_journal_year                    2011
_chemical_formula_sum            'C12 H23 Br O3'
_chemical_formula_weight         295.21
_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                87.120(3)
_cell_angle_beta                 84.110(3)
_cell_angle_gamma                73.262(3)
_cell_formula_units_Z            2
_cell_length_a                   5.2374(10)
_cell_length_b                   8.1373(16)
_cell_length_c                   16.775(3)
_cell_measurement_reflns_used    3200
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      29.10
_cell_measurement_theta_min      2.61
_cell_volume                     680.9(2)
_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      150(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_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  0.0635
_diffrn_reflns_av_sigmaI/netI    0.0912
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            11299
_diffrn_reflns_theta_full        30.96
_diffrn_reflns_theta_max         30.96
_diffrn_reflns_theta_min         2.44
_exptl_absorpt_coefficient_mu    3.011
_exptl_absorpt_correction_T_max  0.9422
_exptl_absorpt_correction_T_min  0.6133
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.494
_refine_diff_density_min         -0.486
_refine_diff_density_rms         0.094
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         4290
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0997
_refine_ls_R_factor_gt           0.0466
_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^)+(0.0240P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0706
_refine_ls_wR_factor_ref         0.0818
_reflns_number_gt                2608
_reflns_number_total             4290
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja2069449_si_008.cif
_cod_data_source_block           abw9s10
_cod_database_code               4106935