Mechanistic studies on the O-directed free-radical hydrostannation of disubstituted acetylenes with Ph3SnH and Et3B and on the iodination of allylically oxygenated alpha-triphenylstannylalkenes.
Dimopoulos, Paschalis; George, Jonathan; Tocher, Derek A.; Manaviazar, Soraya; Hale, Karl J.; Organic letters 7 (2005) 5377–5380; doi:10.1021/ol051937d

data_1506725
_publ_section_title
;
 Mechanistic studies on the O-directed free-radical hydrostannation of
 disubstituted acetylenes with Ph3SnH and Et3B and on the iodination of
 allylically oxygenated alpha-triphenylstannylalkenes.
;
_journal_issue                   24
_journal_name_full               'Organic letters'
_journal_page_first              5377
_journal_page_last               5380
_journal_paper_doi               10.1021/ol051937d
_journal_volume                  7
_journal_year                    2005
_chemical_formula_sum            'C23 H24 O2 Sn'
_chemical_formula_weight         451.11
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 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                 133.184(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   36.529(3)
_cell_length_b                   11.7506(9)
_cell_length_c                   26.095(2)
_cell_measurement_temperature    150(2)
_cell_volume                     8167.3(11)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       '\w rotation with narrow frames'
_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  0.0239
_diffrn_reflns_av_sigmaI/netI    0.0395
_diffrn_reflns_limit_h_max       48
_diffrn_reflns_limit_h_min       -47
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            35806
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         28.31
_diffrn_reflns_theta_min         1.07
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.264
_exptl_absorpt_correction_T_max  0.6451
_exptl_absorpt_correction_T_min  0.5820
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             3648
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.38
_refine_diff_density_max         1.523
_refine_diff_density_min         -0.478
_refine_diff_density_rms         0.081
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.002(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     957
_refine_ls_number_reflns         18562
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0317
_refine_ls_R_factor_gt           0.0309
_refine_ls_shift/su_max          0.210
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0347P)^2^+3.0076P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0735
_refine_ls_wR_factor_ref         0.0741
_reflns_number_gt                18186
_reflns_number_total             18562
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ol051937dsi20051010_114456.cif
_cod_data_source_block           HaleOL3XRAY32
_cod_original_cell_volume        8167.2(11)
_cod_original_sg_symbol_H-M      C2
_cod_database_code               1506725