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_1506728
_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            'C27 H28 O Sn'
_chemical_formula_weight         487.18
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           56
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ab 2ac'
_symmetry_space_group_name_H-M   'P c c n'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   15.4757(9)
_cell_length_b                   40.118(2)
_cell_length_c                   7.2870(4)
_cell_measurement_temperature    150(2)
_cell_volume                     4524.2(4)
_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 0.998
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'Bruker SMART APEX diffractometer'
_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  0.0313
_diffrn_reflns_av_sigmaI/netI    0.0207
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       51
_diffrn_reflns_limit_k_min       -50
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            37670
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         2.01
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.144
_exptl_absorpt_correction_T_max  0.9886
_exptl_absorpt_correction_T_min  0.6211
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1984
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.01
_refine_diff_density_max         3.970
_refine_diff_density_min         -3.302
_refine_diff_density_rms         0.109
_refine_ls_extinction_coef       0.00013(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         5480
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.108
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0505
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0378P)^2^+20.0473P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1135
_refine_ls_wR_factor_ref         0.1158
_reflns_number_gt                5015
_reflns_number_total             5480
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ol051937dsi20051010_114456.cif
_cod_data_source_block           HALEOL3XRAY35
_cod_original_cell_volume        4524.2(5)
_cod_original_sg_symbol_H-M      Pccn
_cod_database_code               1506728