Highly Enantio- and Diastereoselective Mannich Reactions of Chiral Ni(II) Glycinates with Amino Sulfones. Efficient Asymmetric Synthesis of Aromatic α,β-Diamino Acids
Jiang Wang; Ting Shi; Guanghui Deng; Hualiang Jiang; Hong Liu; Journal of Organic Chemistry 73 (2008) 8563–8570; doi:10.1021/jo8019169

data_4023833
_publ_contact_author             'Jiang Wang'
_publ_contact_author_email       wangjjudy@163.com
_publ_section_title
;
 Highly Enantio- and Diastereoselective Mannich Reactions
 of Chiral Ni(II) Glycinates with Amino Sulfones.
 Efficient Asymmetric Synthesis of Aromatic \a,\b-Diamino Acids
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8563
_journal_page_last               8570
_journal_paper_doi               10.1021/jo8019169
_journal_volume                  73
_journal_year                    2008
_chemical_absolute_configuration ad
_chemical_formula_sum            'C39 H40 N4 Ni O5'
_chemical_formula_weight         703.46
_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                90.00
_cell_angle_beta                 94.156(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.9478(16)
_cell_length_b                   8.4269(11)
_cell_length_c                   16.178(2)
_cell_measurement_reflns_used    1700
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      38.014
_cell_measurement_theta_min      5.049
_cell_volume                     1760.5(4)
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  '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  0.1052
_diffrn_reflns_av_sigmaI/netI    0.1403
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10128
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         26.50
_diffrn_reflns_theta_min         1.95
_exptl_absorpt_coefficient_mu    0.600
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7541
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             740
_exptl_crystal_size_max          0.347
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.087
_refine_diff_density_max         0.432
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.013(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.869
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     449
_refine_ls_number_reflns         6967
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      0.871
_refine_ls_R_factor_all          0.0949
_refine_ls_R_factor_gt           0.0615
_refine_ls_shift/su_max          0.048
_refine_ls_shift/su_mean         0.012
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0298P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1133
_refine_ls_wR_factor_ref         0.1280
_reflns_number_gt                4380
_reflns_number_total             6967
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8019169_si_002.cif
_cod_data_source_block           (+)-3a
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4023833