Design and synthesis of (S)- and (R)-α-(phenyl)ethylamine-derived NH-type ligands and their application for the chemical resolution of α-amino acids.
Takeda, Ryosuke; Kawamura, Akie; Kawashima, Aki; Moriwaki, Hiroki; Sato, Tatsunori; Aceña, José Luis; Soloshonok, Vadim A.; Organic & biomolecular chemistry 12 (2014) 6239–6249; doi:10.1039/c4ob00669k

data_7153924
_publ_section_title
;
 Design and synthesis of (S)- and (R)-\a-(phenyl)ethylamine-derived
 NH-type ligands and their application for the chemical resolution of
 \a-amino acids.
;
_journal_issue                   32
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6239
_journal_page_last               6249
_journal_paper_doi               10.1039/c4ob00669k
_journal_volume                  12
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C34 H34 Cl1 N3 Ni1 O4'
_chemical_formula_sum            'C34 H34 Cl N3 Ni O4'
_chemical_formula_weight         642.8
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           76
_symmetry_cell_setting           tetragonal
_symmetry_Int_Tables_number      76
_symmetry_space_group_name_Hall  'P 4w'
_symmetry_space_group_name_H-M   'P 41'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-01-24T16:44:59-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.76204(4)
_cell_length_b                   9.76204(4)
_cell_length_c                   31.9566(2)
_cell_measurement_reflns_used    19516
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.027
_cell_measurement_theta_min      2.744
_cell_measurement_wavelength     1.54184
_cell_volume                     3045.38(3)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -68.00  -42.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.5756   57.0000   60.0000 26

  2 omega    8.00   33.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.5756   57.0000   60.0000 25

  3 omega    6.00   87.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.5756 -125.0000  -90.0000 81

  4 omega   38.00   77.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -45.0000  120.0000 39

  5 omega   39.00   65.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -30.0000 -120.0000 26

  6 omega   30.00   69.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -30.0000   60.0000 39

  7 omega   84.00  155.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   30.0000 -180.0000 71

  8 omega   98.00  157.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  125.0000   90.0000 59

  9 omega   18.00  113.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.5756   38.0000   90.0000 95

 10 omega   73.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.5756 -125.0000  -60.0000 25

 11 omega   11.00   36.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.5756 -125.0000  -60.0000 25

 12 omega   14.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.5756   38.0000    0.0000 94

 13 omega  -99.00   -4.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000   77.0000 -150.0000 95

 14 omega  -33.00   -7.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000   30.0000 -180.0000 26

 15 omega   92.00  122.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609 -125.0000 -180.0000 30

 16 omega   38.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -45.0000 -180.0000 37

 17 omega   76.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -94.0000   30.0000 29

 18 omega   30.00   64.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -30.0000  -60.0000 34

 19 omega   48.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -94.0000  -60.0000 61

 20 omega   30.00   56.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -30.0000  150.0000 26

 21 omega   99.00  133.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -77.0000   90.0000 34

 22 omega   48.00   96.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -77.0000   90.0000 48

 23 omega   37.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -30.0000 -180.0000 26

 24 omega   30.00   69.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -30.0000 -150.0000 39

 25 omega   59.00  119.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609 -125.0000  -60.0000 60

 26 omega   48.00  127.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -61.0000  -30.0000 79

 27 omega   26.00  141.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -15.0000  -30.0000 115

;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Agilent SuperNova'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0300118
_diffrn_orient_matrix_UB_12      0.1274786
_diffrn_orient_matrix_UB_13      -0.0268964
_diffrn_orient_matrix_UB_21      0.1487922
_diffrn_orient_matrix_UB_22      0.0013244
_diffrn_orient_matrix_UB_23      0.0160625
_diffrn_orient_matrix_UB_31      0.0432575
_diffrn_orient_matrix_UB_32      -0.0930165
_diffrn_orient_matrix_UB_33      -0.0366329
_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  0.0234
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            24338
_diffrn_reflns_theta_full        71.44
_diffrn_reflns_theta_max         71.44
_diffrn_reflns_theta_min         4.53
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    2.077
_exptl_absorpt_correction_T_max  0.717
_exptl_absorpt_correction_T_min  0.638
_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    1.402
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.2996
_exptl_crystal_size_mid          0.2481
_exptl_crystal_size_min          0.2095
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.418
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
The Friedel pair coverage of the experiment is almost complete (76%).
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=0.000(3), 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   0.006(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     391
_refine_ls_number_reflns         5213
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.115
_refine_ls_R_factor_all          0.0263
_refine_ls_R_factor_gt           0.0262
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0349P)^2^+1.3458P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0698
_refine_ls_wR_factor_ref         0.0699
_reflns_number_gt                5195
_reflns_number_total             5213
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            c4ob00669k2.cif
_cod_data_source_block           a2013226_solo3phea
_cod_depositor_comments          'Adding full bibliography for 7153924.cif.'
_cod_original_cell_volume        3045.357(19)
_cod_database_code               7153924