Synthesis of α-Amino Acids via Asymmetric Phase Transfer-Catalyzed Alkylation of Achiral Nickel(II) Complexes of Glycine-Derived Schiff Bases
Yuri N. Belokon; Natalia B. Bespalova; Tatiana D. Churkina; Ivana Císařová; Marina G. Ezernitskaya; Syuzanna R. Harutyunyan; Radim Hrdina; Henri B. Kagan; Pavel Kočovský; Konstantin A. Kochetkov; Oleg V. Larionov; Konstantin A. Lyssenko; Michael North; Miroslav Polášek; Alexander S. Peregudov; Vladimir V. Prisyazhnyuk; Štěpán Vyskočil; Journal of the American Chemical Society 125 (2003) 12860–12871; doi:10.1021/ja035465e

data_4114269
_publ_section_title
;
 Synthesis of \a-Amino Acids via Asymmetric Phase Transfer-Catalyzed
 Alkylation of Achiral Nickel(II) Complexes of Glycine-Derived Schiff
 Bases
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12860
_journal_page_last               12871
_journal_paper_doi               10.1021/ja035465e
_journal_volume                  125
_journal_year                    2003
_chemical_formula_moiety         'C21 H15 N3 Ni O3'
_chemical_formula_sum            'C21 H15 N3 Ni O3'
_chemical_formula_weight         416.07
_chemical_melting_point_gt       553
_chemical_name_systematic
;
 glycine and pyridine-2-carboxylic acid(2-benzoyl-phenyl)-amide
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.687(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.783(3)
_cell_length_b                   18.550(4)
_cell_length_c                   7.2338(14)
_cell_measurement_reflns_used    999
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      26
_cell_measurement_theta_min      4
_cell_volume                     1679.8(6)
_computing_cell_refinement       'SMART (Bruker, 1998b)'
_computing_data_collection       'SMART (Bruker, 1998b)'
_computing_data_reduction        'SAINTPlus (Bruker, 1998a)'
_computing_molecular_graphics    'SHELXTL ver. 5.1 (Sheldrick, 1998b)'
_computing_publication_material  'SHELXTL ver. 5.1 (Sheldrick, 1998b)'
_computing_structure_refinement  'SHELXTL ver. 5.1 (Sheldrick, 1998b)'
_computing_structure_solution    'SHELXTL ver. 5.1 (Sheldrick, 1998b)'
_diffrn_ambient_temperature      110(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD area detector'
_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     0.71073
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_av_sigmaI/netI    0.0534
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            9250
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         2.73
_exptl_absorpt_coefficient_mu    1.185
_exptl_absorpt_correction_T_max  0.846
_exptl_absorpt_correction_T_min  0.753
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS(Sheldrick, 1998a)'
_exptl_crystal_density_diffrn    1.645
_exptl_crystal_description       prism
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.679
_refine_diff_density_min         -0.572
_refine_diff_density_rms         0.106
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     313
_refine_ls_number_reflns         3982
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0761
_refine_ls_R_factor_gt           0.0528
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0470P)^2^+1.5000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1150
_refine_ls_wR_factor_ref         0.1228
_reflns_number_gt                2581
_reflns_number_total             3982
_reflns_threshold_expression     I>2s(I)
_cod_data_source_file            ja035465esi20030515_062858_1.cif
_cod_data_source_block           comp_1
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4114269