[2.2]Paracyclophane-Derived Chiral P,N-Ligands: Design, Synthesis, and Application in Palladium-Catalyzed Asymmetric Allylic Alkylation
Biao Jiang; Yang Lei; Xiao-Long Zhao; Journal of Organic Chemistry 73 (2008) 7833–7836; doi:10.1021/jo801373r

data_4023710
_publ_contact_author_address
;     
"Laboratory of Modern Synthetic Organic Chemistry, 
Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 
Shanghai 200032, People's Republic of China"
;
_publ_contact_author_email       jiangb@mail.sioc.ac.cn
_publ_contact_author_fax         64166128
_publ_contact_author_name        'Biao Jiang'
_publ_contact_author_phone       64163300
_publ_section_title
;
 [2.2]Paracyclophane-Derived Chiral P,N-Ligands:
 Design, Synthesis, and Application in Palladium-Catalyzed
 Asymmetric Allylic Alkylation
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7833
_journal_page_last               7836
_journal_paper_doi               10.1021/jo801373r
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C34 H30 N O P'
_chemical_formula_weight         499.56
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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                63.367(2)
_cell_angle_beta                 77.471(2)
_cell_angle_gamma                82.101(2)
_cell_formula_units_Z            2
_cell_length_a                   8.9716(9)
_cell_length_b                   12.9570(13)
_cell_length_c                   13.0562(13)
_cell_measurement_reflns_used    2513
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      53.742
_cell_measurement_theta_min      4.656
_cell_volume                     1323.0(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0546
_diffrn_reflns_av_sigmaI/netI    0.0615
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7803
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.76
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.132
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75123
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.498
_exptl_crystal_size_mid          0.422
_exptl_crystal_size_min          0.347
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.970
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     335
_refine_ls_number_reflns         5612
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.970
_refine_ls_R_factor_all          0.0743
_refine_ls_R_factor_gt           0.0555
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0773P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1382
_refine_ls_wR_factor_ref         0.1477
_reflns_number_gt                4007
_reflns_number_total             5612
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo801373r_si_002.cif
_cod_data_source_block           cd27448
_cod_database_code               4023710