Specific Synthesis of 1,2- and 1,3-Dialkylidenecycloheptanes by [3+2+2] Cyclization of Alkenyl Fischer Carbene Complexes and Allenes
José Barluenga; Rubén Vicente; Pablo Barrio; Luis A. López; Miguel Tomás; Javier Borge; Journal of the American Chemical Society 126 (2004) 14354–14355; doi:10.1021/ja045459y

data_4113142
_publ_contact_author
;     Jos\'e Barluenga
      Instituto Universitario de Qu\'imica Organomet\'alica "Enrique Moles"
      Unidad Asociada al CSIC
      Universidad de Oviedo
      Juli\'an Claver\'ia 8
      33071-Oviedo
      Spain
;
_publ_contact_author_email       barluenga@uniovi.es
_publ_contact_author_fax         '0034 98 5103450'
_publ_contact_author_phone       '0034 98 5103450'
_publ_section_title
;
 Specific Synthesis of 1,2- and 1,3-Dialkylidenecycloheptanes by [3+2+2]
 Cyclization of Alkenyl Fischer Carbene Complexes and Allenes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14354
_journal_page_last               14355
_journal_paper_doi               10.1021/ja045459y
_journal_volume                  126
_journal_year                    2004
_chemical_compound_source        synthesis
_chemical_formula_moiety         'C23 H28 Fe O'
_chemical_formula_sum            'C23 H28 Fe O'
_chemical_formula_weight         376.30
_chemical_name_systematic
; 
6-ferrocenyl-2-4-diisopropylidenecycloheptanone 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 101.4900(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   21.5630(2)
_cell_length_b                   9.0770(2)
_cell_length_c                   10.0990(7)
_cell_measurement_reflns_used    4246
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_cell_volume                     1937.04(14)
_computing_cell_refinement       'HKL SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius BV, 1997-2002)'
_computing_data_reduction
'HKL DENZO and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2001)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'DIRDIF-99 (Beurskens et al., 1999)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'horizontally mounted graphite crystal'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.061
_diffrn_reflns_av_sigmaI/netI    0.0533
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            15619
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         1.93
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.786
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.382
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'XABS2 (Parkin et al., 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             800
_exptl_crystal_preparation
;
 Crystallization solvent: dichloromethane and diethylether 
;
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.400
_refine_diff_density_min         -0.568
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         4405
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0897
_refine_ls_R_factor_gt           0.0583
_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^)+(0.0943P)^2^+0.9312P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1525
_refine_ls_wR_factor_ref         0.1777
_reflns_number_gt                3044
_reflns_number_total             4405
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja045459ysi20040728_111901.cif
_cod_data_source_block           6f
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4113142