2-Phospha[3]ferrocenophanes with Planar Chirality: Synthesis and Use in Enantioselective Organocatalytic [3 + 2] Cyclizations
Arnaud Voituriez; Armen Panossian; Nicolas Fleury-Brégeot; Pascal Retailleau; Angela Marinetti; Journal of the American Chemical Society 130 (2008) 14030–14031; doi:10.1021/ja806060a

data_4108561
_publ_contact_author_address
;ICSN-CNRS
1 avenue de la Terrasse
91198 Gif sur Yvette
;
_publ_contact_author_email       angela.marinetti@icsn.cnrs-gif.fr
_publ_contact_author_fax         0169077247
_publ_contact_author_name        'Marinetti, Angela'
_publ_contact_author_phone       0169823036
_publ_section_title
;
 2-Phospha[3]ferrocenophanes with Planar Chirality: Synthesis and Use in
 Enantioselective Organocatalytic [3 + 2] Cyclizations
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14030
_journal_page_last               14031
_journal_paper_doi               10.1021/ja806060a
_journal_volume                  130
_journal_year                    2008
_chemical_formula_moiety         'C24 H39 Fe P Si2'
_chemical_formula_sum            'C24 H39 Fe P Si2'
_chemical_formula_weight         470.55
_chemical_name_systematic
; 
 ? 
;
_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                90.000
_cell_angle_beta                 108.875(5)
_cell_angle_gamma                90.000
_cell_formula_units_Z            2
_cell_length_a                   8.789(4)
_cell_length_b                   12.145(5)
_cell_length_c                   13.013(5)
_cell_measurement_reflns_used    1545
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.26
_cell_measurement_theta_min      0.41
_cell_volume                     1314.3(10)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997); COLLECT (Nonius B.V., 1999)'
_computing_data_collection
'DENZO (Otwinowski & Minor, 1997); COLLECT (Nonius B.V., 1999)'
_computing_data_reduction        'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement
'SHELXL97 (Sheldrick, 2008); CRYSTALBUILDER (Welter, 2006)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Nonius kappa-CCD diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0478
_diffrn_reflns_av_sigmaI/netI    0.0613
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5500
_diffrn_reflns_theta_full        21.29
_diffrn_reflns_theta_max         21.29
_diffrn_reflns_theta_min         1.65
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.733
_exptl_absorpt_correction_T_max  0.85
_exptl_absorpt_correction_T_min  0.64
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Scalepack (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.189
_exptl_crystal_description       prism
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881; 1152 Friedel pairs'
_refine_ls_abs_structure_Flack   0.01(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         2704
_refine_ls_number_restraints     13
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0806
_refine_ls_R_factor_gt           0.0528
_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^)+(0.0630P)^2^+0.6746P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1074
_refine_ls_wR_factor_ref         0.1205
_reflns_number_gt                2033
_reflns_number_total             2705
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja806060a_si_002_2.cif
_cod_data_source_block           compound_5c
_cod_database_code               4108561