Second-order asymmetric transformation and its application for the practical synthesis of α-amino acids.
Takeda, Ryosuke; Kawamura, Akie; Kawashima, Aki; Sato, Tatsunori; Moriwaki, Hiroki; Izawa, Kunisuke; Abe, Hidenori; Soloshonok, Vadim A.; Organic & biomolecular chemistry 16 (2018) 4968–4972; doi:10.1039/c8ob00963e

data_7156288
_publ_section_title
;
 Second-order asymmetric transformation and its application for the
 practical synthesis of \a-amino acids.
;
_journal_issue                   27
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4968
_journal_page_last               4972
_journal_paper_doi               10.1039/c8ob00963e
_journal_volume                  16
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C35 H36 Cl N3 Ni O3, C H4 O'
_chemical_formula_sum            'C36 H40 Cl N3 Ni O4'
_chemical_formula_weight         672.87
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-09-30T14:50:17-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2018-04-24 deposited with the CCDC.
2018-06-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.23830(10)
_cell_length_b                   15.3670(2)
_cell_length_c                   32.9494(5)
_cell_measurement_reflns_used    13638
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.236
_cell_measurement_theta_min      2.645
_cell_measurement_wavelength     1.54184
_cell_volume                     3158.66(8)
_computing_cell_refinement
'CrysAlis Pro (Oxford Diffraction Ltd., 2011)'
_computing_data_collection
'CrysAlis Pro (Oxford Diffraction Ltd., 2011)'
_computing_data_reduction
'CrysAlis Pro (Oxford Diffraction Ltd., 2011)'
_computing_molecular_graphics    'Diamond v.3.2f (Crystal Impact GbR, 2008)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'OLEX2 (Dolomanov et al, 2009)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2012
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_details
;
  1 omega -109.00  -21.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.9506  -57.0000 -150.0000 88

  2 omega    3.00   96.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       40.9506 -125.0000   90.0000 93

  3 omega  -48.00  -22.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -15.0000  -90.0000 26

  4 omega -139.00  -92.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -15.0000  -90.0000 47

  5 omega   43.00   73.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  150.0000 30

  6 omega   35.00   60.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   30.0000 25

  7 omega   53.00  107.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -94.0000  -90.0000 54

  8 omega   29.00  108.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -94.0000 -180.0000 79

  9 omega   36.00   69.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000 -150.0000 33

 10 omega   84.00  157.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  -30.0000 73

 11 omega   39.00  116.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000   30.0000 77

 12 omega   40.00   66.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   60.0000 26

 13 omega   84.00  156.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000  -30.0000 72

 14 omega  124.00  154.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  -90.0000 30

 15 omega   35.00   63.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   90.0000 28

 16 omega  -61.00    7.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.9506   37.0000    0.0000 68

 17 omega   57.00   92.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       40.9506 -125.0000  -30.0000 35

 18 omega   11.00  110.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       40.9506   77.0000  150.0000 99

 19 omega  -48.00  -21.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000   45.0000 -150.0000 27

 20 omega   48.00   77.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000 -180.0000 29

 21 omega   43.00   69.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  -90.0000 26

 22 omega   36.00   64.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  -30.0000 28

 23 omega   42.00  135.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000   30.0000 93

 24 omega   88.00  114.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000  120.0000 26

 25 omega   66.00  114.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000 -120.0000 48

 26 omega  101.00  151.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000 -120.0000 50

 27 omega   55.00   96.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   15.0000  120.0000 41

 28 omega  109.00  157.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   15.0000  120.0000 48

 29 omega   39.00   67.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000  120.0000 28

 30 omega   43.00   69.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -94.0000   90.0000 26

 31 omega  126.00  152.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000 -180.0000 26

 32 omega   39.00  103.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000  -90.0000 64

;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Agilent SuperNova'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0451856
_diffrn_orient_matrix_UB_12      -0.0201403
_diffrn_orient_matrix_UB_13      -0.0449986
_diffrn_orient_matrix_UB_21      -0.0611086
_diffrn_orient_matrix_UB_22      0.0940519
_diffrn_orient_matrix_UB_23      -0.0113888
_diffrn_orient_matrix_UB_31      0.2349137
_diffrn_orient_matrix_UB_32      0.0282663
_diffrn_orient_matrix_UB_33      0.0056911
_diffrn_radiation_monochromator  'Multilayer optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Nova (Cu) X-ray micro-source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0528
_diffrn_reflns_av_unetI/netI     0.0407
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            28325
_diffrn_reflns_theta_full        75
_diffrn_reflns_theta_max         75
_diffrn_reflns_theta_min         2.68
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    2.026
_exptl_absorpt_correction_T_max  0.909
_exptl_absorpt_correction_T_min  0.615
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
        (compiled Dec  3 2012,18:21:49)
Analytical numeric absorption correction using a multifaceted crystal
                        model based on expressions derived by R.C. Clark & J.S.
        (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1416
_exptl_crystal_size_max          0.464
_exptl_crystal_size_mid          0.0759
_exptl_crystal_size_min          0.0496
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
The Friedel pair coverage of the experiment is almost complete (100%).
Analysis of the absolute structure using likelihood methods
(Hooft, Straver & Spek, 2008) was performed using PLATON (Spek, 2011).
 The results indicated that the absolute structure had been correctly
 assigned. The method calculated that the probability that the structure 
is inverted is smaller than 10-99. The absolute structure parameter y 
(Hooft, Straver & Spek, 2008) was calculated using PLATON (Spek,
2010). The resulting value was y=-0.024(8), which together with Flack parameter 
value, indicate that the absolute structure has sureley been determined 
correctly.

Flack, H. D. (1983), Acta Cryst. A39, 876-881
Flack & G. Bernardinelli, Acta Cryst. 1999, A55, 908-915; 
H. D. Flack & G. Bernardinelli, J. Appl. Cryst. 2000, 33, 1143-1148.

R. W. W. Hooft, L. H. Straver & A. L. Spek, J. Appl. Cryst. 2008, 41, 96-103
A. L. Spek (2010) PLATON, Utrecht, The Netherlands; 
A. L. Spek, J. Appl. Cryst. 2003, 36, 7-13
A. L. Thompson & D. J. Watkin, Tetrahedron: Asymmetry 2009, 20, 712--717

;
_refine_ls_abs_structure_Flack   -0.025(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     413
_refine_ls_number_reflns         6489
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0288
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0343P)^2^+0.2930P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0691
_refine_ls_wR_factor_ref         0.0702
_reflns_number_gt                6227
_reflns_number_total             6489
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            c8ob00963e2.cif
_cod_data_source_block           a2014151_solo1phg
_cod_depositor_comments          'Adding full bibliography for 7156288.cif.'
_cod_database_code               7156288