Studies on the Mechanism, Selectivity, and Synthetic Utility of Lactone Reduction Using SmI2 and H2O
Dixit Parmar; Lorna A. Duffy; Dhandapani V. Sadasivam; Hiroshi Matsubara; Paul A. Bradley; Robert A. Flowers; David J. Procter; Journal of the American Chemical Society 131 (2009) 15467–15473; doi:10.1021/ja906396u

data_4105197
_publ_section_title
;
 Studies on the Mechanism, Selectivity, and Synthetic Utility of Lactone
 Reduction Using SmI2 and H2O
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15467
_journal_page_last               15473
_journal_paper_doi               10.1021/ja906396u
_journal_volume                  131
_journal_year                    2009
_chemical_formula_sum            'C22 H23 Br O4'
_chemical_formula_weight         431.31
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 96.076(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.202(2)
_cell_length_b                   9.2582(15)
_cell_length_c                   17.370(3)
_cell_measurement_reflns_used    965
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.34
_cell_measurement_theta_min      2.75
_cell_volume                     1951.2(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0302
_diffrn_reflns_av_sigmaI/netI    0.0356
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -21
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_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.36
_exptl_absorpt_coefficient_mu    2.131
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.751
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_description       block
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.398
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3967
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0312
_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^)+(0.0394P)^2^+0.7479P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0741
_refine_ls_wR_factor_ref         0.0784
_reflns_number_gt                3298
_reflns_number_total             3967
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja906396u_si_002.cif
_cod_data_source_block           z:\s3218\work\s3218abs
_cod_original_cell_volume        1951.3(6)
_cod_database_code               4105197