Two Approaches to Diverting the Course of a Free-Radical Cyclization: Application of Cyclopropylcarbinyl Radical Fragmentations and Allenes as Radical Acceptors
Dexi Yang; Valerie Cwynar; Matthew G. Donahue; David J. Hart; Grace Mbogo; Journal of Organic Chemistry 74 (2009) 8726–8732; doi:10.1021/jo901834q

data_4025048
_publ_section_title
;
Two Approaches to Diverting the Course of a Free-Radical Cyclization:
Application of Cyclopropylcarbinyl Radical Fragmentations and Allenes as
Radical Acceptors
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8726
_journal_page_last               8732
_journal_paper_doi               10.1021/jo901834q
_journal_volume                  74
_journal_year                    2009
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C16 H26 O3 Si1'
_chemical_formula_sum            'C16 H26 O3 Si'
_chemical_formula_weight         294.46
_chemical_name_common            'Hart 1731'
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      61
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             2009-08-20T17:20:09-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.1345(1)
_cell_length_b                   18.9292(2)
_cell_length_c                   15.6921(2)
_cell_measurement_reflns_used    4252
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      2.037
_cell_measurement_wavelength     0.71073
_cell_volume                     3307.38(6)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_orient_matrix_type       'by Nonius Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      -0.572566E-1
_diffrn_orient_matrix_UB_12      -0.691914E-1
_diffrn_orient_matrix_UB_13      0.4894E-3
_diffrn_orient_matrix_UB_21      -0.446783E-1
_diffrn_orient_matrix_UB_22      0.367831E-1
_diffrn_orient_matrix_UB_23      -0.266814E-1
_diffrn_orient_matrix_UB_31      0.168743E-1
_diffrn_orient_matrix_UB_32      -0.14303E-1
_diffrn_orient_matrix_UB_33      -0.479742E-1
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.048
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            41862
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.15
_diffrn_source                   'Enraf Nonius FR590'
_exptl_absorpt_coefficient_mu    0.147
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.183
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'rectangular plate'
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3789
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.037
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0503P)^2^+0.7394P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0919
_refine_ls_wR_factor_ref         0.0993
_reflns_number_gt                2894
_reflns_number_total             3789
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            jo901834q_si_008.cif
_cod_data_source_block           Hart1731
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               4025048