Addition of amines to nitriles catalyzed by ytterbium amides: an efficient one-step synthesis of monosubstituted N-arylamidines.
Wang, Junfeng; Xu, Fan; Cai, Tao; Shen, Qi; Organic letters 10 (2008) 445–448; doi:10.1021/ol702739c

data_1504500
_publ_section_title
;
 Addition of amines to nitriles catalyzed by ytterbium amides: an
 efficient one-step synthesis of monosubstituted N-arylamidines.
;
_journal_issue                   3
_journal_name_full               'Organic letters'
_journal_page_first              445
_journal_page_last               448
_journal_paper_doi               10.1021/ol702739c
_journal_volume                  10
_journal_year                    2008
_chemical_formula_moiety         'C19 H24 N2'
_chemical_formula_sum            'C19 H24 N2'
_chemical_formula_weight         280.40
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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                 93.313(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.3234(16)
_cell_length_b                   14.786(2)
_cell_length_c                   10.2105(15)
_cell_measurement_reflns_used    6015
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      25.3
_cell_measurement_theta_min      3.1
_cell_volume                     1706.7(4)
_computing_cell_refinement       CrystalClear
_computing_data_collection       CrystalClear
_computing_data_reduction        CrystalStructure
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      223(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_av_sigmaI/netI    0.0249
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            16338
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.09
_exptl_absorpt_coefficient_mu    0.064
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_correction_T_min  0.807
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.091
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.47
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.148
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         3116
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.148
_refine_ls_R_factor_all          0.0822
_refine_ls_R_factor_gt           0.0713
_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^)+(0.0787P)^2^+0.8655P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1784
_refine_ls_wR_factor_ref         0.1852
_reflns_number_gt                2758
_reflns_number_total             3116
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol702739c-file001.cif
_cod_data_source_block           compound
_cod_original_cell_volume        1706.6(4)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1504500