Fe-Catalyzed Allylic C-C-Bond Activation: Vinylcyclopropanes As Versatile a1,a3,d5-Synthons in Traceless Allylic Substitutions and [3 + 2]-Cycloadditions
André P. Dieskau; Michael S. Holzwarth; Bernd Plietker; Journal of the American Chemical Society 134 (2012) 5048–5051; doi:10.1021/ja300294a

data_4117717
_publ_section_title
;
 Fe-Catalyzed Allylic C-C-Bond Activation: Vinylcyclopropanes As Versatile
 a1,a3,d5-Synthons in Traceless Allylic Substitutions and [3 +
 2]-Cycloadditions
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5048
_journal_page_last               5051
_journal_paper_doi               10.1021/ja300294a
_journal_volume                  134
_journal_year                    2012
_chemical_formula_moiety         'C22 H17 N3 O2 S'
_chemical_formula_sum            'C22 H17 N3 O2 S'
_chemical_formula_weight         387.45
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 106.753(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   27.215(3)
_cell_length_b                   9.5265(9)
_cell_length_c                   15.1182(13)
_cell_measurement_reflns_used    2891
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.43
_cell_measurement_theta_min      1.56
_cell_volume                     3753.2(6)
_computing_cell_refinement       'Bruker APEX II Software Suite, 2008'
_computing_data_collection       'Bruker APEX II Software Suite, 2008'
_computing_data_reduction        'Bruker APEX II Software Suite, 2008'
_computing_molecular_graphics    'SHELXTL-plus, XP (Sheldrick, 1991)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker Kappa APEX II Duo'
_diffrn_measurement_method       'Omega + Phi Scans'
_diffrn_radiation_monochromator  Triumph
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0377
_diffrn_reflns_av_sigmaI/netI    0.0464
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13102
_diffrn_reflns_theta_full        26.43
_diffrn_reflns_theta_max         26.43
_diffrn_reflns_theta_min         1.56
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.196
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Blessing, 1995'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_description       block
_exptl_crystal_F_000             1616
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3829
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0588
_refine_ls_R_factor_gt           0.0366
_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^)+(0.0401P)^2^+1.3134P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0822
_refine_ls_wR_factor_ref         0.0883
_reflns_number_gt                2891
_reflns_number_total             3829
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja300294a_si_004.cif
_cod_data_source_block           s1854lm
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4117717