Regioselective carboindation of simple alkenes with indium tribromide and ketene silyl acetals.
Nishimoto, Yoshihiro; Ueda, Hiroki; Inamoto, Yoshihiro; Yasuda, Makoto; Baba, Akio; Organic letters 12 (2010) 3390–3393; doi:10.1021/ol1012108

data_1503074
_publ_section_title
;
 Regioselective carboindation of simple alkenes with indium tribromide and
 ketene silyl acetals.
;
_journal_issue                   15
_journal_name_full               'Organic letters'
_journal_page_first              3390
_journal_page_last               3393
_journal_paper_doi               10.1021/ol1012108
_journal_volume                  12
_journal_year                    2010
_chemical_formula_moiety         'C13 H25 Br2 In O2 '
_chemical_formula_sum            'C13 H25 Br2 In O2'
_chemical_formula_weight         487.97
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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                108.628(2)
_cell_angle_beta                 94.419(2)
_cell_angle_gamma                101.340(2)
_cell_formula_units_Z            2
_cell_length_a                   6.8758(4)
_cell_length_b                   10.8208(7)
_cell_length_c                   12.6521(6)
_cell_measurement_reflns_used    9115
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      30.5
_cell_measurement_theta_min      3.1
_cell_volume                     864.64(9)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.1599
_diffrn_reflns_av_sigmaI/netI    0.1296
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5183
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.06
_exptl_absorpt_coefficient_mu    5.982
_exptl_absorpt_correction_T_max  0.3808
_exptl_absorpt_correction_T_min  0.1539
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_process_details   refdelf_exptl_absorpt_process_details
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.874
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             476
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_refine_diff_density_max         5.565
_refine_diff_density_min         -2.926
_refine_diff_density_rms         0.398
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         3047
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0852
_refine_ls_R_factor_gt           0.0794
_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^)+(0.1250P)^2^+0.0610P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1762
_refine_ls_wR_factor_ref         0.1805
_reflns_number_gt                2734
_reflns_number_total             3047
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol1012108_si_002.cif
_cod_data_source_block           3aa
_cod_original_cell_volume        864.65(9)
_cod_original_formula_sum        'C13 H25 Br2 In O2 '
_cod_database_code               1503074