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_4117715
_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         'C23 H17 N3 O'
_chemical_formula_sum            'C23 H17 N3 O'
_chemical_formula_weight         351.40
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                91.016(16)
_cell_angle_beta                 93.314(14)
_cell_angle_gamma                95.991(13)
_cell_formula_units_Z            4
_cell_length_a                   9.627(3)
_cell_length_b                   11.363(4)
_cell_length_c                   16.729(6)
_cell_measurement_reflns_used    3580
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.99
_cell_measurement_theta_min      1.8
_cell_volume                     1816.5(11)
_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 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0692
_diffrn_reflns_av_sigmaI/netI    0.1253
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            16639
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         1.80
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.7086
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Blessing, 1995'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       0.0046(3)
_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   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     488
_refine_ls_number_reflns         6376
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.1294
_refine_ls_R_factor_gt           0.0543
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0070P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0630
_refine_ls_wR_factor_ref         0.0711
_reflns_number_gt                3580
_reflns_number_total             6376
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja300294a_si_002.cif
_cod_data_source_block           s1852lm
_cod_database_code               4117715