#------------------------------------------------------------------------------
#$Date: 2016-03-22 11:44:04 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178913 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/42/4114270.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4114270
loop_
_publ_author_name
'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'
_publ_section_title
;
 Synthesis of α-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         'C22 H17 N3 Ni O3'
_chemical_formula_sum            'C22 H17 N3 Ni O3'
_chemical_formula_weight         430.10
_chemical_melting_point_gt       550
_chemical_name_systematic
;
 (R,S)-alanine and pyridine-2-carboxylic acid(2-benzoyl-phenyl)-amide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 110.403(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.987(4)
_cell_length_b                   21.557(8)
_cell_length_c                   10.936(5)
_cell_measurement_reflns_used    1024
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      26
_cell_measurement_theta_min      3
_cell_volume                     1764.8(14)
_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 0.982
_diffrn_measured_fraction_theta_max 0.982
_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  0.0458
_diffrn_reflns_av_sigmaI/netI    0.0773
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10376
_diffrn_reflns_theta_full        27.55
_diffrn_reflns_theta_max         27.55
_diffrn_reflns_theta_min         2.74
_exptl_absorpt_coefficient_mu    1.131
_exptl_absorpt_correction_T_max  0.943
_exptl_absorpt_correction_T_min  0.852
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS(Sheldrick, 1998a)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.619
_exptl_crystal_description       prism
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.823
_refine_diff_density_min         -0.744
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.935
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     360
_refine_ls_number_reflns         4008
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.935
_refine_ls_R_factor_all          0.1058
_refine_ls_R_factor_gt           0.0537
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0657P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1161
_refine_ls_wR_factor_ref         0.1341
_reflns_number_gt                2088
_reflns_number_total             4008
_reflns_threshold_expression     I>2s(I)
_cod_data_source_file            ja035465esi20030515_062858_2.cif
_cod_data_source_block           comp3a
_cod_original_cell_volume        1764.9(14)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4114270
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.21091(8) 0.05130(2) 0.34893(4) 0.0480(2) Uani 1 1 d . A .
O1 O 0.1437(4) 0.08731(10) 0.1846(2) 0.0442(7) Uani 1 1 d . A .
O2 O 0.0245(3) 0.17384(10) 0.0785(2) 0.0355(6) Uani 1 1 d . A .
O3 O 0.3612(4) -0.09025(11) 0.5887(2) 0.0468(7) Uani 1 1 d . . .
N1 N 0.2779(6) -0.02191(14) 0.2844(3) 0.0684(12) Uani 1 1 d . . .
N2 N 0.2582(4) 0.00792(12) 0.5059(3) 0.0442(8) Uani 1 1 d . . .
N3 N 0.1588(4) 0.12644(12) 0.4084(3) 0.0311(7) Uani 1 1 d . . .
C1' C 0.2282(12) -0.0374(4) 0.1568(8) 0.0331(18) Uani 0.50 1 d P A 1
H1'A H 0.1584 -0.0101 0.0904 0.040 Uiso 0.50 1 calc PR A 1
C2' C 0.2834(13) -0.0951(4) 0.1266(9) 0.037(2) Uani 0.50 1 d P A 1
H2'A H 0.2580 -0.1065 0.0380 0.044 Uiso 0.50 1 calc PR A 1
C3' C 0.375(4) -0.1354(7) 0.225(3) 0.054(7) Uani 0.50 1 d P A 1
H3'A H 0.4324 -0.1708 0.2060 0.065 Uiso 0.50 1 calc PR A 1
C1" C 0.3369(13) -0.0250(4) 0.1715(8) 0.039(2) Uani 0.50 1 d P A 2
H1"A H 0.3464 0.0119 0.1268 0.047 Uiso 0.50 1 calc PR A 2
C2" C 0.3785(14) -0.0819(4) 0.1304(9) 0.041(2) Uani 0.50 1 d P A 2
H2"A H 0.3977 -0.0855 0.0497 0.050 Uiso 0.50 1 calc PR A 2
C3" C 0.392(4) -0.1350(11) 0.212(2) 0.061(8) Uani 0.50 1 d P A 2
H3"A H 0.4075 -0.1754 0.1824 0.074 Uiso 0.50 1 calc PR A 2
C4 C 0.3810(5) -0.12496(17) 0.3423(4) 0.0414(10) Uani 1 1 d . . .
C5 C 0.3265(5) -0.06734(16) 0.3711(3) 0.0408(9) Uani 1 1 d . A .
C6 C 0.3187(5) -0.05134(15) 0.5027(3) 0.0338(8) Uani 1 1 d . A .
C7 C 0.2262(7) 0.03014(17) 0.6162(4) 0.0571(12) Uani 1 1 d . A .
C8 C 0.1587(5) 0.09181(15) 0.6191(3) 0.0395(9) Uani 1 1 d . . .
C9 C 0.1222(6) 0.11020(17) 0.7305(4) 0.0416(9) Uani 1 1 d . A .
C10" C 0.1048(18) 0.0727(9) 0.8221(17) 0.042(4) Uani 0.50 1 d P A 1
H10A H 0.0625 0.0881 0.8874 0.050 Uiso 0.50 1 calc PR A 1
C11" C 0.1488(12) 0.0121(4) 0.8202(7) 0.0350(18) Uani 0.50 1 d P A 1
H11A H 0.1494 -0.0148 0.8891 0.042 Uiso 0.50 1 calc PR A 1
C12" C 0.1935(12) -0.0103(3) 0.7153(8) 0.0318(19) Uani 0.50 1 d P A 1
H12A H 0.2034 -0.0539 0.7071 0.038 Uiso 0.50 1 calc PR A 1
C10' C 0.1843(17) 0.0739(8) 0.8474(17) 0.040(4) Uani 0.50 1 d P A 2
H10B H 0.1653 0.0877 0.9241 0.049 Uiso 0.50 1 calc PR A 2
C11' C 0.2754(13) 0.0166(4) 0.8475(8) 0.044(2) Uani 0.50 1 d P A 2
H11B H 0.3129 -0.0081 0.9243 0.052 Uiso 0.50 1 calc PR A 2
C12' C 0.3099(13) -0.0035(4) 0.7394(8) 0.038(2) Uani 0.50 1 d P A 2
H12B H 0.3855 -0.0381 0.7442 0.046 Uiso 0.50 1 calc PR A 2
C13 C 0.1327(4) 0.13796(14) 0.5168(3) 0.0293(8) Uani 1 1 d . A .
C14 C 0.0716(5) 0.20191(15) 0.5381(3) 0.0294(8) Uani 1 1 d . . .
C15 C -0.1085(5) 0.21682(17) 0.4829(3) 0.0342(8) Uani 1 1 d . A .
C16 C -0.1668(6) 0.27635(18) 0.4985(4) 0.0387(9) Uani 1 1 d . . .
C17 C -0.0467(6) 0.32039(17) 0.5708(4) 0.0396(9) Uani 1 1 d . A .
C18 C 0.1325(6) 0.30569(16) 0.6259(4) 0.0364(9) Uani 1 1 d . . .
C19 C 0.1913(6) 0.24673(15) 0.6094(3) 0.0331(9) Uani 1 1 d . A .
C20 C 0.1430(5) 0.17649(14) 0.3116(3) 0.0295(8) Uani 1 1 d . A .
C21 C 0.0944(5) 0.14495(15) 0.1791(3) 0.0310(8) Uani 1 1 d . . .
C22 C 0.3194(6) 0.21021(17) 0.3413(4) 0.0353(9) Uani 1 1 d . . .
H22C H 0.360(4) 0.2333(14) 0.425(3) 0.031(9) Uiso 1 1 d . . .
H22B H 0.417(5) 0.1805(17) 0.352(4) 0.049(11) Uiso 1 1 d . . .
H22A H 0.310(4) 0.2358(14) 0.277(3) 0.025(9) Uiso 1 1 d . . .
H9 H 0.079(4) 0.1522(17) 0.728(3) 0.040(10) Uiso 1 1 d . . .
H4 H 0.412(5) -0.1546(16) 0.396(3) 0.038(10) Uiso 1 1 d . . .
H15 H -0.183(5) 0.1883(15) 0.431(3) 0.032(10) Uiso 1 1 d . . .
H20 H 0.049(4) 0.2078(14) 0.310(3) 0.030(9) Uiso 1 1 d . . .
H11 H -0.276(4) 0.2852(14) 0.461(3) 0.019(9) Uiso 1 1 d . . .
H17 H -0.092(4) 0.3641(16) 0.582(3) 0.043(10) Uiso 1 1 d . . .
H19 H 0.304(4) 0.2384(14) 0.644(3) 0.024(10) Uiso 1 1 d . . .
H18 H 0.221(5) 0.3362(18) 0.680(4) 0.053(11) Uiso 1 1 d . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N3 Ni1 O1 87.12(11)
N3 Ni1 N2 96.51(12)
O1 Ni1 N2 173.27(12)
N3 Ni1 N1 175.42(15)
O1 Ni1 N1 90.68(12)
N2 Ni1 N1 86.09(13)
C21 O1 Ni1 115.2(2)
C5 N1 C1' 117.6(4)
C5 N1 C1" 118.0(4)
C1' N1 C1" 35.5(4)
C5 N1 Ni1 113.8(3)
C1' N1 Ni1 125.0(4)
C1" N1 Ni1 124.7(4)
C6 N2 C7 120.8(3)
C6 N2 Ni1 113.8(2)
C7 N2 Ni1 125.4(2)
C13 N3 C20 120.8(3)
C13 N3 Ni1 128.1(2)
C20 N3 Ni1 111.0(2)
N1 C1' C2' 117.4(7)
C3' C2' C1' 120.2(13)
C4 C3' C2' 119.6(18)
C2" C1" N1 119.7(7)
C1" C2" C3" 118.9(14)
C2" C3" C4 117.7(17)
C3' C4 C5 118.5(8)
C3' C4 C3" 6(3)
C5 C4 C3" 118.7(10)
N1 C5 C4 122.4(4)
N1 C5 C6 114.6(3)
C4 C5 C6 123.0(3)
O3 C6 N2 129.0(3)
O3 C6 C5 119.2(3)
N2 C6 C5 111.8(3)
N2 C7 C8 121.1(3)
N2 C7 C12' 117.4(5)
C8 C7 C12' 119.3(4)
N2 C7 C12" 124.0(4)
C8 C7 C12" 111.4(4)
C12' C7 C12" 34.9(4)
C9 C8 C7 118.2(3)
C9 C8 C13 117.1(3)
C7 C8 C13 124.7(3)
C10" C9 C8 126.0(9)
C10" C9 C10' 24.7(8)
C8 C9 C10' 120.6(9)
C9 C10" C11" 118.6(16)
C10" C11" C12" 119.1(11)
C11" C12" C7 123.7(6)
C9 C10' C11' 119.3(15)
C12' C11' C10' 121.6(10)
C11' C12' C7 118.1(8)
N3 C13 C8 123.1(3)
N3 C13 C14 118.6(3)
C8 C13 C14 118.3(3)
C15 C14 C19 119.2(3)
C15 C14 C13 119.1(3)
C19 C14 C13 121.7(3)
C14 C15 C16 119.9(4)
C17 C16 C15 120.4(4)
C18 C17 C16 119.9(4)
C17 C18 C19 119.9(4)
C18 C19 C14 120.7(4)
N3 C20 C22 110.7(3)
N3 C20 C21 106.5(2)
C22 C20 C21 109.1(3)
O2 C21 O1 124.6(3)
O2 C21 C20 121.1(3)
O1 C21 C20 114.2(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Ni1 N3 1.846(3)
Ni1 O1 1.857(2)
Ni1 N2 1.874(3)
Ni1 N1 1.881(3)
O1 C21 1.299(4)
O2 C21 1.217(4)
O3 C6 1.217(4)
N1 C5 1.323(4)
N1 C1' 1.353(8)
N1 C1" 1.469(9)
N2 C6 1.370(4)
N2 C7 1.402(5)
N3 C13 1.297(4)
N3 C20 1.486(4)
C1' C2' 1.397(11)
C2' C3' 1.38(2)
C3' C4 1.29(3)
C1" C2" 1.386(11)
C2" C3" 1.43(3)
C3" C4 1.48(3)
C4 C5 1.388(5)
C5 C6 1.503(5)
C7 C8 1.439(5)
C7 C12' 1.469(9)
C7 C12" 1.483(8)
C8 C9 1.405(5)
C8 C13 1.456(4)
C9 C10" 1.33(2)
C9 C10' 1.431(17)
C10" C11" 1.35(2)
C11" C12" 1.401(11)
C10' C11' 1.43(2)
C11' C12' 1.374(11)
C13 C14 1.507(4)
C14 C15 1.390(5)
C14 C19 1.392(5)
C15 C16 1.396(5)
C16 C17 1.385(5)
C17 C18 1.382(5)
C18 C19 1.388(5)
C20 C22 1.517(5)
C20 C21 1.523(4)
