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_4113141
_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         'C20 H26 O2'
_chemical_formula_sum            'C20 H26 O2'
_chemical_formula_weight         298.41
_chemical_name_systematic
; 
3,4-diisopropylidene-6-(4-methoxyphenyl)cycloheptanone 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 91.368(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.9680(2)
_cell_length_b                   10.4305(2)
_cell_length_c                   11.6086(3)
_cell_measurement_reflns_used    2460
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      70.36
_cell_measurement_theta_min      3.81
_cell_volume                     843.47(4)
_computing_cell_refinement       'SMART 5.625 (Bruker AXS, 1997-2001) (b)'
_computing_data_collection       'SMART 5.625 (Bruker AXS, 1997-2001) (b)'
_computing_data_reduction        'SAINT+ NT 6.04 (Bruker AXS, 1997-2001) (a)'
_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      100(2)
_diffrn_measured_fraction_theta_full 0.857
_diffrn_measured_fraction_theta_max 0.857
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_sigmaI/netI    0.0358
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3567
_diffrn_reflns_theta_full        70.36
_diffrn_reflns_theta_max         70.36
_diffrn_reflns_theta_min         3.81
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.575
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.741
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2.03 (Sheldrick, 1997-2001)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.175
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             324
_exptl_crystal_preparation
;
 Crystallization solvent: hexane
;
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2341
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0590
_refine_ls_R_factor_gt           0.0563
_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^)+(0.1023P)^2^+0.4699P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1574
_refine_ls_wR_factor_ref         0.1614
_reflns_number_gt                2227
_reflns_number_total             2341
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja045459ysi20040728_111844.cif
_cod_data_source_block           4a
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4113141