#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/79/2227984.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_2227984
loop_
_publ_author_name
'Yu, Jun'
_publ_section_title
;
 trans-Bis(ethylenediamine)bis{2-[N-(2-hydroxyethyl)oxamoylamino]benzoato}nickel(II)
;
_journal_coeditor_code           SI2287
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1140
_journal_paper_doi               10.1107/S1600536810032848
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          '[Ni (C11 H11 N2 O5)2 (C2 H8 N2)2]'
_chemical_formula_moiety         'C26 H38 N8 Ni O10'
_chemical_formula_sum            'C26 H38 N8 Ni O10'
_chemical_formula_weight         681.35
_chemical_name_systematic
;
trans-Bis(ethylenediamine)bis{2-[N-(2-
hydroxyethyl)oxamoylamino]benzoato}nickel(II)
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                109.589(3)
_cell_angle_beta                 95.720(3)
_cell_angle_gamma                103.788(3)
_cell_formula_units_Z            1
_cell_length_a                   8.266(2)
_cell_length_b                   10.122(3)
_cell_length_c                   10.260(3)
_cell_measurement_reflns_used    2252
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.008
_cell_measurement_theta_min      2.576
_cell_volume                     770.2(4)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       'φ and ω 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  0.0157
_diffrn_reflns_av_sigmaI/netI    0.0311
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4112
_diffrn_reflns_theta_full        25.24
_diffrn_reflns_theta_max         25.24
_diffrn_reflns_theta_min         2.23
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.698
_exptl_absorpt_correction_T_max  0.8965
_exptl_absorpt_correction_T_min  0.8449
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             358
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.395
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         2735
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0330
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0403P)²+0.1720P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0784
_refine_ls_wR_factor_ref         0.0840
_reflns_number_gt                2385
_reflns_number_total             2735
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            si2287.cif
_cod_data_source_block           I
_cod_original_cell_volume        770.1(4)
_cod_database_code               2227984
_cod_database_fobs_code          2227984
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni Ni1 0.0000 0.5000 0.5000 0.03350(13) Uani d S 1 . .
O O1 0.12334(19) 0.66239(15) 0.42423(15) 0.0405(4) Uani d . 1 . .
O O2 0.1944(3) 0.52116(18) 0.2362(2) 0.0746(6) Uani d . 1 . .
O O3 0.2826(2) 1.19597(16) 0.59663(16) 0.0515(4) Uani d . 1 . .
O O4 0.0627(2) 0.92690(17) 0.70836(18) 0.0548(4) Uani d . 1 . .
O O5 0.3278(2) 1.3059(2) 1.0935(2) 0.0739(6) Uani d . 1 . .
H H5A 0.3030 1.3824 1.1274 0.111 Uiso calc R 1 . .
N N1 0.2153(2) 0.94573(18) 0.49224(17) 0.0349(4) Uani d . 1 . .
H H1 0.1599 0.8678 0.5030 0.042 Uiso calc R 1 . .
N N2 0.1282(2) 1.1741(2) 0.80736(19) 0.0435(4) Uani d . 1 . .
H H2 0.1738 1.2541 0.7958 0.052 Uiso calc R 1 . .
C C1 0.1939(3) 0.6434(2) 0.3180(2) 0.0411(5) Uani d . 1 . .
C C2 0.2816(2) 0.7770(2) 0.2880(2) 0.0353(5) Uani d . 1 . .
C C3 0.3576(3) 0.7547(3) 0.1703(2) 0.0451(5) Uani d . 1 . .
H H3 0.3529 0.6597 0.1141 0.054 Uiso calc R 1 . .
C C4 0.4394(3) 0.8697(3) 0.1350(3) 0.0493(6) Uani d . 1 . .
H H4 0.4900 0.8525 0.0563 0.059 Uiso calc R 1 . .
C C5 0.4454(3) 1.0099(3) 0.2174(3) 0.0501(6) Uani d . 1 . .
H H5 0.4996 1.0878 0.1935 0.060 Uiso calc R 1 . .
C C6 0.3726(3) 1.0370(3) 0.3347(2) 0.0442(5) Uani d . 1 . .
H H6 0.3780 1.1328 0.3893 0.053 Uiso calc R 1 . .
C C7 0.2905(2) 0.9221(2) 0.3726(2) 0.0335(4) Uani d . 1 . .
C C8 0.2178(3) 1.0721(2) 0.5916(2) 0.0358(5) Uani d . 1 . .
C C9 0.1276(3) 1.0487(2) 0.7090(2) 0.0376(5) Uani d . 1 . .
C C10 0.0570(3) 1.1848(3) 0.9330(2) 0.0462(6) Uani d . 1 . .
H H10A -0.0433 1.1021 0.9102 0.055 Uiso calc R 1 . .
H H10B 0.0221 1.2736 0.9637 0.055 Uiso calc R 1 . .
C C11 0.1807(3) 1.1869(3) 1.0509(2) 0.0515(6) Uani d . 1 . .
H H11A 0.1260 1.1908 1.1308 0.062 Uiso calc R 1 . .
H H11B 0.2125 1.0966 1.0210 0.062 Uiso calc R 1 . .
N N3 0.2112(2) 0.42116(19) 0.49185(19) 0.0400(4) Uani d . 1 . .
H H3A 0.1841 0.3313 0.4960 0.048 Uiso calc R 1 . .
H H3B 0.2471 0.4148 0.4106 0.048 Uiso calc R 1 . .
N N4 0.1301(2) 0.63455(19) 0.70438(19) 0.0418(4) Uani d . 1 . .
H H4A 0.1743 0.7267 0.7092 0.050 Uiso calc R 1 . .
H H4B 0.0590 0.6360 0.7655 0.050 Uiso calc R 1 . .
C C12 0.3456(3) 0.5236(3) 0.6128(3) 0.0516(6) Uani d . 1 . .
H H12A 0.4037 0.6070 0.5916 0.062 Uiso calc R 1 . .
H H12B 0.4281 0.4752 0.6321 0.062 Uiso calc R 1 . .
C C13 0.2663(3) 0.5744(3) 0.7395(3) 0.0518(6) Uani d . 1 . .
H H13A 0.2202 0.4928 0.7675 0.062 Uiso calc R 1 . .
H H13B 0.3519 0.6490 0.8178 0.062 Uiso calc R 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N3 Ni1 N3 2_566 . 180.0000(10) ?
N3 Ni1 N4 2_566 2_566 83.44(7) ?
N3 Ni1 N4 . 2_566 96.56(7) ?
N3 Ni1 N4 2_566 . 96.56(7) ?
N3 Ni1 N4 . . 83.44(7) ?
N4 Ni1 N4 2_566 . 180.0000(10) ?
N3 Ni1 O1 2_566 . 90.32(6) ?
N3 Ni1 O1 . . 89.68(6) ?
N4 Ni1 O1 2_566 . 90.28(7) ?
N4 Ni1 O1 . . 89.72(7) ?
N3 Ni1 O1 2_566 2_566 89.68(6) ?
N3 Ni1 O1 . 2_566 90.32(6) ?
N4 Ni1 O1 2_566 2_566 89.72(7) ?
N4 Ni1 O1 . 2_566 90.28(7) ?
O1 Ni1 O1 . 2_566 180.0000(10) ?
C1 O1 Ni1 . . 127.60(13) ?
C11 O5 H5A . . 109.5 ?
C8 N1 C7 . . 129.14(17) ?
C8 N1 H1 . . 115.4 ?
C7 N1 H1 . . 115.4 ?
C9 N2 C10 . . 124.2(2) ?
C9 N2 H2 . . 117.9 ?
C10 N2 H2 . . 117.9 ?
O2 C1 O1 . . 123.6(2) ?
O2 C1 C2 . . 118.0(2) ?
O1 C1 C2 . . 118.39(19) ?
C3 C2 C7 . . 118.33(19) ?
C3 C2 C1 . . 117.89(19) ?
C7 C2 C1 . . 123.78(19) ?
C4 C3 C2 . . 121.8(2) ?
C4 C3 H3 . . 119.1 ?
C2 C3 H3 . . 119.1 ?
C5 C4 C3 . . 119.2(2) ?
C5 C4 H4 . . 120.4 ?
C3 C4 H4 . . 120.4 ?
C4 C5 C6 . . 121.0(2) ?
C4 C5 H5 . . 119.5 ?
C6 C5 H5 . . 119.5 ?
C5 C6 C7 . . 120.5(2) ?
C5 C6 H6 . . 119.8 ?
C7 C6 H6 . . 119.8 ?
C6 C7 N1 . . 122.06(19) ?
C6 C7 C2 . . 119.2(2) ?
N1 C7 C2 . . 118.73(17) ?
O3 C8 N1 . . 127.5(2) ?
O3 C8 C9 . . 120.27(19) ?
N1 C8 C9 . . 112.28(17) ?
O4 C9 N2 . . 125.4(2) ?
O4 C9 C8 . . 122.18(19) ?
N2 C9 C8 . . 112.47(19) ?
N2 C10 C11 . . 112.25(19) ?
N2 C10 H10A . . 109.2 ?
C11 C10 H10A . . 109.2 ?
N2 C10 H10B . . 109.2 ?
C11 C10 H10B . . 109.2 ?
H10A C10 H10B . . 107.9 ?
O5 C11 C10 . . 112.9(2) ?
O5 C11 H11A . . 109.0 ?
C10 C11 H11A . . 109.0 ?
O5 C11 H11B . . 109.0 ?
C10 C11 H11B . . 109.0 ?
H11A C11 H11B . . 107.8 ?
C12 N3 Ni1 . . 107.92(14) ?
C12 N3 H3A . . 110.1 ?
Ni1 N3 H3A . . 110.1 ?
C12 N3 H3B . . 110.1 ?
Ni1 N3 H3B . . 110.1 ?
H3A N3 H3B . . 108.4 ?
C13 N4 Ni1 . . 107.42(14) ?
C13 N4 H4A . . 110.2 ?
Ni1 N4 H4A . . 110.2 ?
C13 N4 H4B . . 110.2 ?
Ni1 N4 H4B . . 110.2 ?
H4A N4 H4B . . 108.5 ?
N3 C12 C13 . . 108.87(18) ?
N3 C12 H12A . . 109.9 ?
C13 C12 H12A . . 109.9 ?
N3 C12 H12B . . 109.9 ?
C13 C12 H12B . . 109.9 ?
H12A C12 H12B . . 108.3 ?
N4 C13 C12 . . 109.39(19) ?
N4 C13 H13A . . 109.8 ?
C12 C13 H13A . . 109.8 ?
N4 C13 H13B . . 109.8 ?
C12 C13 H13B . . 109.8 ?
H13A C13 H13B . . 108.2 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Ni1 N3 2_566 2.0829(18) ?
Ni1 N3 . 2.0829(18) y
Ni1 N4 2_566 2.0847(18) ?
Ni1 N4 . 2.0847(18) y
Ni1 O1 . 2.1357(14) y
Ni1 O1 2_566 2.1357(14) ?
O1 C1 . 1.267(3) ?
O2 C1 . 1.242(3) ?
O3 C8 . 1.222(2) ?
O4 C9 . 1.219(3) ?
O5 C11 . 1.401(3) ?
O5 H5A . 0.8200 ?
N1 C8 . 1.336(3) ?
N1 C7 . 1.406(3) ?
N1 H1 . 0.8600 ?
N2 C9 . 1.329(3) ?
N2 C10 . 1.452(3) ?
N2 H2 . 0.8600 ?
C1 C2 . 1.518(3) ?
C2 C3 . 1.392(3) ?
C2 C7 . 1.413(3) ?
C3 C4 . 1.379(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.373(4) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.374(3) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.394(3) ?
C6 H6 . 0.9300 ?
C8 C9 . 1.533(3) ?
C10 C11 . 1.495(3) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
N3 C12 . 1.471(3) ?
N3 H3A . 0.9000 ?
N3 H3B . 0.9000 ?
N4 C13 . 1.470(3) ?
N4 H4A . 0.9000 ?
N4 H4B . 0.9000 ?
C12 C13 . 1.505(3) ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N3 H3A O3 1_545 0.90 2.22 2.976(2) 141.7
N4 H4B O2 2_566 0.90 2.30 3.001(3) 134.2
O5 H5A O2 1_566 0.82 1.94 2.727(3) 159.9
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N3 Ni1 O1 C1 2_566 . . . -129.94(18) ?
N3 Ni1 O1 C1 . . . . 50.06(18) ?
N4 Ni1 O1 C1 2_566 . . . -46.50(18) ?
N4 Ni1 O1 C1 . . . . 133.50(18) ?
O1 Ni1 O1 C1 2_566 . . . 5E1(10) ?
Ni1 O1 C1 O2 . . . . 3.4(3) ?
Ni1 O1 C1 C2 . . . . -177.07(13) ?
O2 C1 C2 C3 . . . . 0.0(3) ?
O1 C1 C2 C3 . . . . -179.48(19) ?
O2 C1 C2 C7 . . . . -179.9(2) ?
O1 C1 C2 C7 . . . . 0.5(3) ?
C7 C2 C3 C4 . . . . -0.2(3) ?
C1 C2 C3 C4 . . . . 179.78(19) ?
C2 C3 C4 C5 . . . . -0.4(4) ?
C3 C4 C5 C6 . . . . 0.6(4) ?
C4 C5 C6 C7 . . . . -0.1(4) ?
C5 C6 C7 N1 . . . . 179.67(19) ?
C5 C6 C7 C2 . . . . -0.6(3) ?
C8 N1 C7 C6 . . . . -5.3(3) ?
C8 N1 C7 C2 . . . . 174.97(19) ?
C3 C2 C7 C6 . . . . 0.8(3) ?
C1 C2 C7 C6 . . . . -179.26(19) ?
C3 C2 C7 N1 . . . . -179.53(18) ?
C1 C2 C7 N1 . . . . 0.5(3) ?
C7 N1 C8 O3 . . . . 2.7(4) ?
C7 N1 C8 C9 . . . . -176.75(18) ?
C10 N2 C9 O4 . . . . 2.7(4) ?
C10 N2 C9 C8 . . . . -177.83(18) ?
O3 C8 C9 O4 . . . . -179.3(2) ?
N1 C8 C9 O4 . . . . 0.1(3) ?
O3 C8 C9 N2 . . . . 1.2(3) ?
N1 C8 C9 N2 . . . . -179.35(18) ?
C9 N2 C10 C11 . . . . 86.0(3) ?
N2 C10 C11 O5 . . . . 60.6(3) ?
N3 Ni1 N3 C12 2_566 . . . -10E1(10) ?
N4 Ni1 N3 C12 2_566 . . . 166.19(14) ?
N4 Ni1 N3 C12 . . . . -13.81(14) ?
O1 Ni1 N3 C12 . . . . 75.94(14) ?
O1 Ni1 N3 C12 2_566 . . . -104.06(14) ?
N3 Ni1 N4 C13 2_566 . . . 165.48(14) ?
N3 Ni1 N4 C13 . . . . -14.52(14) ?
N4 Ni1 N4 C13 2_566 . . . 0E1(10) ?
O1 Ni1 N4 C13 . . . . -104.23(15) ?
O1 Ni1 N4 C13 2_566 . . . 75.77(15) ?
Ni1 N3 C12 C13 . . . . 39.4(2) ?
Ni1 N4 C13 C12 . . . . 40.2(2) ?
N3 C12 C13 N4 . . . . -54.1(2) ?
