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Acta Cryst. (2007). E63, m2664
https://doi.org/10.1107/S1600536807048027
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Retracted: Bis[2-(2-hydroxy­benzoyl­hydrazono)­propionato]nickel(II) trihydrate

W.-P. Wu, F.-C. Zeng and Y. Wu
In the title compound, [Ni(C10H9N2O4)2]·3H2O, the Ni2+ ion is octa­hedrally coordinated by carboxyl and acyl O atoms and azomethine N atoms of two tridentate 2-(2-hydroxy­benzoyl­hydrazono)propionate ligands, each of which forms two five-membered chelate rings sharing the N—Ni bond. The occurrence of O—H...N and O—H...O hydrogen bonds between water mol­ecules and ligands results in the formation of an intricate three-dimensional network which stabilizes the packing.
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Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807048027/dn2235sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807048027/dn2235Isup2.hkl
Contains datablock I

CCDC reference: 669120

checkCIF report

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.045
  • wR factor = 0.116
  • Data-to-parameter ratio = 13.0

checkCIF/PLATON results

No syntax errors found




Alert level C
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal  (x 10000)        200 Deg.
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Ni1    -   O4      ..       8.33 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Ni1    -   O7      ..       5.97 su
PLAT417_ALERT_2_C Short Inter D-H..H-D       H9B    ..  H10A    ..       2.12 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact  O6     ..  C12     ..       3.00 Ang.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          4
              H2 O


Alert level G
PLAT794_ALERT_5_G Check Predicted Bond Valency for Ni1         (2)       2.04


   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check
Comment top

Hydrazones have attracted considerable interest due to their complicated coordination behavior and pharmacological activity. Many of physiologically active hydrazone-metal complexes find application in the treatment of several diseases such as tuberculosis, tumour, cancer and so on (Rodriguez-Argelles et al., 2004; Buss et al., 2003). This paper reports the crystal structure of a novel Ni(II) complexe with N-(2-propionic acid)-salicyloyl hydrazone.

In complex (I), the Ni2+ ion is octahedrally surrounded by two tridentate N-(2-propionacid)-salicyloyl hydrazone ligands(Fig.1). The linkage of two tridentate ligands to Ni2+ ion is accomplished through the acyl oxygen, carboxyl oxygen and imido nitrogen, resulting in the formation of two five-membered chelate rings sharing the same edge. The atoms O1, N1, O4 and N3 are nearly coplanar and located in the equatorial plane, while two oxygen atoms of another ligand occupy the axial sites, the angle of the axial O5—Ni—O7 is 150° which deviates significantly from the linear angle of 180°. Those data indicate that the Ni atom is in distorted octahedron geometry·Comparing with the distances of C—O(1.42 Å) and C=O(1.23 Å), the bond lengths of O7—C14 and O4—C4 are 1.228 Å and 1.246 Å, respectively, indicating that these bonds are double linkage and the ligand functions as a keto form.

The occurrence of O—H···N and O—H···O hydrogen bondings between water molecules and ligands results in the formation of an intricated three dimensionnal network which stabilizes the packing (Table 1).

Related literature top

For related literature, see: Buss et al. (2003); He et al. (2002); Rodriguez-Argelles et al. (2004).

Experimental top

The ligand was prepared according to the literature(He et al. 2002). Pyruvic acid is biochemical reagent and all other chemicals used were of analytical grade.

The ligand H3L(25.1 mg, 0.12 mmol))and NiSO4 (11.8 mg, 0.05 mmol), were added in a mixed solvent of ethanol and acetonitrile, the mixture was heated for five hours under reflux. during the process stirring and influx were required. The resultant was then filtered to give a pure solution which was infiltrated by diethyl ether freely in a closed vessel, a weeks later some single crystals of the size suitable for X-Ray diffraction analysis.

Refinement top

The water H atoms were located in a difference Fourier map and they were refined freely with a distance restraint of O—H=0.85 (1) Å. The others H atoms were positioned geometrically and treated as riding on their parent atoms, with C—H distances of 0.93 Å (pyridine ring), 0.86 Å (amine group), and with Uiso(H) 1.2Ueq(C).

Structure description top

Hydrazones have attracted considerable interest due to their complicated coordination behavior and pharmacological activity. Many of physiologically active hydrazone-metal complexes find application in the treatment of several diseases such as tuberculosis, tumour, cancer and so on (Rodriguez-Argelles et al., 2004; Buss et al., 2003). This paper reports the crystal structure of a novel Ni(II) complexe with N-(2-propionic acid)-salicyloyl hydrazone.

In complex (I), the Ni2+ ion is octahedrally surrounded by two tridentate N-(2-propionacid)-salicyloyl hydrazone ligands(Fig.1). The linkage of two tridentate ligands to Ni2+ ion is accomplished through the acyl oxygen, carboxyl oxygen and imido nitrogen, resulting in the formation of two five-membered chelate rings sharing the same edge. The atoms O1, N1, O4 and N3 are nearly coplanar and located in the equatorial plane, while two oxygen atoms of another ligand occupy the axial sites, the angle of the axial O5—Ni—O7 is 150° which deviates significantly from the linear angle of 180°. Those data indicate that the Ni atom is in distorted octahedron geometry·Comparing with the distances of C—O(1.42 Å) and C=O(1.23 Å), the bond lengths of O7—C14 and O4—C4 are 1.228 Å and 1.246 Å, respectively, indicating that these bonds are double linkage and the ligand functions as a keto form.

The occurrence of O—H···N and O—H···O hydrogen bondings between water molecules and ligands results in the formation of an intricated three dimensionnal network which stabilizes the packing (Table 1).

For related literature, see: Buss et al. (2003); He et al. (2002); Rodriguez-Argelles et al. (2004).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 (Bruker, 2004); data reduction: APEX2 (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Bruker, 2001).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of (I) with the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii. Hydrogen bonds are shown as dashed lines.
Bis[2-(2-hydroxybenzoylhydrazono)propionato]nickel(II) trihydrate top
Crystal data top
[Ni(C10H9N2O4)2]·3H2OZ = 2
Mr = 555.14F(000) = 576
Triclinic, P1Dx = 1.575 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.3787 (12) ÅCell parameters from 4104 reflections
b = 10.7935 (14) Åθ = 1.9–25.1°
c = 11.8795 (15) ŵ = 0.90 mm−1
α = 86.447 (2)°T = 298 K
β = 81.805 (2)°Block, green
γ = 79.847 (2)°0.32 × 0.27 × 0.14 mm
V = 1170.8 (3) Å3
Data collection top
Bruker APEXII area-detector
diffractometer		4271 independent reflections
Radiation source: fine-focus sealed tube3173 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.017
φ and ω scansθmax = 25.1°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −10→11
Tmin = 0.762, Tmax = 0.883k = −12→12
5974 measured reflectionsl = −14→8
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0459P)2 + 0.9257P]
where P = (Fo2 + 2Fc2)/3
4271 reflections(Δ/σ)max = 0.026
329 parametersΔρmax = 0.41 e Å−3
0 restraintsΔρmin = −0.37 e Å−3
Crystal data top
[Ni(C10H9N2O4)2]·3H2Oγ = 79.847 (2)°
Mr = 555.14V = 1170.8 (3) Å3
Triclinic, P1Z = 2
a = 9.3787 (12) ÅMo Kα radiation
b = 10.7935 (14) ŵ = 0.90 mm−1
c = 11.8795 (15) ÅT = 298 K
α = 86.447 (2)°0.32 × 0.27 × 0.14 mm
β = 81.805 (2)°
Data collection top
Bruker APEXII area-detector
diffractometer		4271 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		3173 reflections with I > 2σ(I)
Tmin = 0.762, Tmax = 0.883Rint = 0.017
5974 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0450 restraints
wR(F2) = 0.116H-atom parameters constrained
S = 1.03Δρmax = 0.41 e Å−3
4271 reflectionsΔρmin = −0.37 e Å−3
329 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ni10.03633 (5)0.24821 (4)0.73989 (4)0.04088 (16)
O1−0.1184 (3)0.4062 (2)0.72823 (19)0.0515 (6)
O2−0.2371 (3)0.5249 (3)0.6003 (2)0.0682 (8)
O30.1561 (3)−0.0084 (2)0.3587 (2)0.0526 (6)
H30.1593−0.03880.29660.079*
O40.1846 (3)0.0895 (2)0.6819 (2)0.0542 (7)
O5−0.1161 (3)0.1231 (2)0.8180 (2)0.0520 (6)
O6−0.1891 (3)0.0383 (2)0.9881 (2)0.0557 (7)
O70.2082 (3)0.3690 (2)0.75660 (19)0.0535 (7)
O80.1911 (3)0.4664 (2)1.08922 (19)0.0479 (6)
H80.17810.50641.14740.072*
N10.0160 (3)0.2538 (2)0.5790 (2)0.0401 (6)
N20.1001 (3)0.1580 (3)0.5177 (2)0.0443 (7)
H20.09840.15190.44610.053*
N30.0438 (3)0.2508 (2)0.9057 (2)0.0385 (6)
N40.1266 (3)0.3302 (2)0.9400 (2)0.0423 (7)
H40.12840.34091.01090.051*
C1−0.1541 (4)0.4325 (3)0.6284 (3)0.0432 (8)
C2−0.0796 (4)0.3390 (3)0.5391 (3)0.0408 (8)
C3−0.1218 (4)0.3499 (4)0.4230 (3)0.0558 (10)
H3A−0.04690.30060.37260.084*
H3B−0.13340.43650.39670.084*
H3C−0.21230.31960.42440.084*
C40.1869 (4)0.0730 (3)0.5787 (3)0.0418 (8)
C50.2799 (4)−0.0343 (3)0.5215 (3)0.0405 (8)
C60.2656 (4)−0.0715 (3)0.4127 (3)0.0431 (8)
C70.3629 (4)−0.1724 (4)0.3644 (3)0.0558 (10)
H70.3541−0.19690.29240.067*
C80.4727 (4)−0.2367 (4)0.4224 (4)0.0656 (11)
H8A0.5379−0.30350.38860.079*
C90.4865 (5)−0.2027 (4)0.5299 (4)0.0662 (11)
H90.5597−0.24700.56920.079*
C100.3911 (4)−0.1030 (4)0.5781 (3)0.0557 (10)
H100.4006−0.08040.65060.067*
C11−0.1220 (4)0.1103 (3)0.9248 (3)0.0421 (8)
C12−0.0357 (4)0.1912 (3)0.9795 (3)0.0396 (8)
C13−0.0482 (4)0.1976 (3)1.1052 (3)0.0467 (9)
H13A0.04770.18701.12760.070*
H13B−0.09800.13201.14080.070*
H13C−0.10240.27801.12840.070*
C140.2061 (4)0.3916 (3)0.8568 (3)0.0408 (8)
C150.2854 (4)0.4859 (3)0.8933 (3)0.0407 (8)
C160.2739 (3)0.5245 (3)1.0053 (3)0.0384 (7)
C170.3467 (4)0.6181 (3)1.0295 (3)0.0463 (8)
H170.33910.64281.10400.056*
C180.4302 (4)0.6752 (4)0.9443 (4)0.0568 (10)
H180.47740.73930.96120.068*
C190.4446 (4)0.6377 (4)0.8334 (4)0.0588 (10)
H190.50240.67550.77600.071*
C200.3733 (4)0.5445 (3)0.8085 (3)0.0515 (9)
H200.38340.51970.73370.062*
O90.6479 (4)−0.0977 (3)0.8717 (3)0.0988 (12)
H9A0.5683−0.04510.86310.148*
H9B0.6945−0.06110.91370.148*
O100.3963 (5)0.0695 (5)0.8494 (4)0.155 (2)
H10A0.33890.04750.90730.233*
H10B0.34680.08940.79350.233*
O110.8003 (4)−0.2489 (3)0.7025 (3)0.0849 (10)
H11A0.7474−0.20630.75720.127*
H11B0.7640−0.31560.69660.127*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0518 (3)0.0373 (3)0.0334 (3)−0.00219 (19)−0.00861 (19)−0.00908 (18)
O10.0721 (17)0.0454 (14)0.0345 (13)0.0031 (12)−0.0114 (12)−0.0091 (11)
O20.084 (2)0.0558 (16)0.0591 (17)0.0200 (15)−0.0234 (16)−0.0124 (14)
O30.0710 (17)0.0503 (15)0.0379 (14)−0.0022 (13)−0.0172 (13)−0.0141 (11)
O40.0695 (17)0.0569 (15)0.0348 (13)0.0005 (13)−0.0116 (12)−0.0121 (12)
O50.0742 (17)0.0474 (14)0.0402 (14)−0.0170 (13)−0.0164 (13)−0.0086 (11)
O60.0670 (17)0.0522 (15)0.0513 (16)−0.0209 (13)−0.0062 (13)−0.0007 (13)
O70.0672 (17)0.0638 (16)0.0318 (13)−0.0149 (13)−0.0063 (12)−0.0102 (12)
O80.0635 (16)0.0489 (14)0.0335 (13)−0.0163 (12)−0.0008 (12)−0.0127 (11)
N10.0469 (16)0.0391 (15)0.0344 (15)−0.0065 (13)−0.0028 (13)−0.0108 (12)
N20.0549 (18)0.0443 (16)0.0309 (15)0.0018 (14)−0.0054 (13)−0.0100 (13)
N30.0439 (16)0.0330 (14)0.0407 (16)−0.0057 (12)−0.0113 (13)−0.0084 (12)
N40.0534 (17)0.0422 (15)0.0340 (15)−0.0108 (13)−0.0097 (13)−0.0066 (12)
C10.052 (2)0.0374 (18)0.041 (2)−0.0045 (16)−0.0120 (17)−0.0051 (15)
C20.050 (2)0.0374 (18)0.0356 (18)−0.0074 (15)−0.0084 (16)−0.0029 (14)
C30.068 (3)0.058 (2)0.041 (2)−0.003 (2)−0.0129 (19)−0.0069 (18)
C40.047 (2)0.0449 (19)0.0343 (18)−0.0084 (16)−0.0054 (15)−0.0088 (15)
C50.0432 (19)0.0435 (18)0.0346 (18)−0.0076 (15)−0.0037 (15)−0.0033 (15)
C60.047 (2)0.0422 (19)0.0405 (19)−0.0086 (16)−0.0054 (16)−0.0044 (15)
C70.063 (3)0.055 (2)0.046 (2)−0.0040 (19)0.0023 (19)−0.0160 (18)
C80.059 (3)0.062 (3)0.068 (3)0.010 (2)0.001 (2)−0.016 (2)
C90.057 (2)0.069 (3)0.066 (3)0.008 (2)−0.009 (2)−0.007 (2)
C100.059 (2)0.064 (2)0.044 (2)0.000 (2)−0.0144 (19)−0.0079 (18)
C110.050 (2)0.0358 (18)0.040 (2)−0.0028 (16)−0.0080 (16)−0.0046 (15)
C120.0442 (19)0.0343 (17)0.0395 (19)0.0014 (15)−0.0111 (16)−0.0048 (15)
C130.057 (2)0.046 (2)0.0378 (19)−0.0022 (17)−0.0145 (17)−0.0056 (16)
C140.0428 (19)0.0427 (18)0.0353 (19)−0.0010 (15)−0.0063 (15)−0.0048 (15)
C150.0409 (18)0.0411 (18)0.0384 (19)−0.0020 (15)−0.0051 (15)−0.0037 (15)
C160.0370 (18)0.0366 (17)0.0390 (18)0.0010 (14)−0.0061 (15)−0.0003 (14)
C170.044 (2)0.0427 (19)0.053 (2)−0.0035 (16)−0.0104 (17)−0.0076 (17)
C180.050 (2)0.047 (2)0.077 (3)−0.0114 (18)−0.015 (2)−0.002 (2)
C190.052 (2)0.057 (2)0.066 (3)−0.0160 (19)−0.001 (2)0.010 (2)
C200.052 (2)0.057 (2)0.043 (2)−0.0045 (18)−0.0066 (18)0.0032 (18)
O90.092 (2)0.102 (3)0.108 (3)−0.033 (2)0.002 (2)−0.040 (2)
O100.111 (3)0.260 (6)0.082 (3)−0.012 (4)−0.008 (3)0.023 (3)
O110.108 (3)0.073 (2)0.074 (2)−0.0278 (19)0.0084 (19)−0.0113 (17)
Geometric parameters (Å, º) top
Ni1—N11.943 (3)C5—C61.408 (4)
Ni1—N31.983 (3)C6—C71.387 (5)
Ni1—O12.046 (2)C7—C81.381 (5)
Ni1—O42.092 (2)C7—H70.9300
Ni1—O52.207 (3)C8—C91.381 (6)
Ni1—O72.281 (3)C8—H8A0.9300
O1—C11.280 (4)C9—C101.370 (5)
O2—C11.213 (4)C9—H90.9300
O3—C61.348 (4)C10—H100.9300
O3—H30.8200C11—C121.519 (5)
O4—C41.247 (4)C12—C131.487 (4)
O5—C111.262 (4)C13—H13A0.9600
O6—C111.237 (4)C13—H13B0.9600
O7—C141.226 (4)C13—H13C0.9600
O8—C161.365 (4)C14—C151.480 (5)
O8—H80.8200C15—C201.401 (5)
N1—C21.285 (4)C15—C161.403 (4)
N1—N21.365 (3)C16—C171.380 (5)
N2—C41.360 (4)C17—C181.373 (5)
N2—H20.8600C17—H170.9300
N3—C121.285 (4)C18—C191.383 (6)
N3—N41.368 (4)C18—H180.9300
N4—C141.362 (4)C19—C201.370 (5)
N4—H40.8600C19—H190.9300
C1—C21.518 (4)C20—H200.9300
C2—C31.480 (5)O9—H9A0.8690
C3—H3A0.9600O9—H9B0.8622
C3—H3B0.9600O10—H10A0.8594
C3—H3C0.9600O10—H10B0.8587
C4—C51.462 (4)O11—H11A0.8629
C5—C101.398 (5)O11—H11B0.8594
N1—Ni1—N3175.96 (11)O3—C6—C7121.8 (3)
N1—Ni1—O178.86 (10)O3—C6—C5118.8 (3)
N3—Ni1—O197.27 (10)C7—C6—C5119.5 (3)
N1—Ni1—O477.80 (10)C8—C7—C6120.6 (4)
N3—Ni1—O4106.07 (10)C8—C7—H7119.7
O1—Ni1—O4156.66 (9)C6—C7—H7119.7
N1—Ni1—O5103.83 (10)C9—C8—C7120.6 (4)
N3—Ni1—O575.31 (10)C9—C8—H8A119.7
O1—Ni1—O596.27 (10)C7—C8—H8A119.7
O4—Ni1—O589.12 (10)C10—C9—C8119.2 (4)
N1—Ni1—O7106.13 (10)C10—C9—H9120.4
N3—Ni1—O774.89 (10)C8—C9—H9120.4
O1—Ni1—O790.70 (10)C9—C10—C5122.0 (4)
O4—Ni1—O795.93 (10)C9—C10—H10119.0
O5—Ni1—O7150.01 (9)C5—C10—H10119.0
C1—O1—Ni1114.5 (2)O6—C11—O5126.7 (3)
C6—O3—H3109.5O6—C11—C12117.5 (3)
C4—O4—Ni1113.0 (2)O5—C11—C12115.8 (3)
C11—O5—Ni1113.5 (2)N3—C12—C13126.1 (3)
C14—O7—Ni1110.0 (2)N3—C12—C11112.6 (3)
C16—O8—H8109.5C13—C12—C11121.3 (3)
C2—N1—N2124.4 (3)C12—C13—H13A109.5
C2—N1—Ni1119.8 (2)C12—C13—H13B109.5
N2—N1—Ni1115.6 (2)H13A—C13—H13B109.5
C4—N2—N1114.8 (3)C12—C13—H13C109.5
C4—N2—H2122.6H13A—C13—H13C109.5
N1—N2—H2122.6H13B—C13—H13C109.5
C12—N3—N4120.5 (3)O7—C14—N4120.1 (3)
C12—N3—Ni1122.4 (2)O7—C14—C15122.8 (3)
N4—N3—Ni1116.8 (2)N4—C14—C15117.0 (3)
C14—N4—N3117.0 (3)C20—C15—C16117.9 (3)
C14—N4—H4121.5C20—C15—C14117.2 (3)
N3—N4—H4121.5C16—C15—C14124.8 (3)
O2—C1—O1125.9 (3)O8—C16—C17121.2 (3)
O2—C1—C2119.1 (3)O8—C16—C15118.6 (3)
O1—C1—C2115.0 (3)C17—C16—C15120.3 (3)
N1—C2—C3127.4 (3)C18—C17—C16120.5 (3)
N1—C2—C1111.6 (3)C18—C17—H17119.7
C3—C2—C1120.9 (3)C16—C17—H17119.7
C2—C3—H3A109.5C17—C18—C19120.2 (4)
C2—C3—H3B109.5C17—C18—H18119.9
H3A—C3—H3B109.5C19—C18—H18119.9
C2—C3—H3C109.5C20—C19—C18119.8 (4)
H3A—C3—H3C109.5C20—C19—H19120.1
H3B—C3—H3C109.5C18—C19—H19120.1
O4—C4—N2118.7 (3)C19—C20—C15121.3 (4)
O4—C4—C5122.0 (3)C19—C20—H20119.4
N2—C4—C5119.3 (3)C15—C20—H20119.4
C10—C5—C6118.2 (3)H9A—O9—H9B105.9
C10—C5—C4117.8 (3)H10A—O10—H10B108.5
C6—C5—C4124.1 (3)H11A—O11—H11B108.1
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O5i0.821.812.606 (3)162
O8—H8···O1ii0.821.772.584 (3)170
N2—H2···O30.862.022.622 (3)126
N2—H2···O11iii0.862.182.826 (4)132
N4—H4···O80.861.912.571 (3)133
O9—H9A···O100.871.872.741 (6)178
O9—H9B···O6iv0.861.982.838 (4)171
O10—H10A···O6v0.862.052.882 (5)163
O10—H10B···O40.862.162.978 (5)160
O11—H11A···O90.861.882.741 (4)173
O11—H11B···O2vi0.862.132.890 (4)148
Symmetry codes: (i) −x, −y, −z+1; (ii) −x, −y+1, −z+2; (iii) −x+1, −y, −z+1; (iv) x+1, y, z; (v) −x, −y, −z+2; (vi) x+1, y−1, z.

Experimental details

Crystal data
Chemical formula[Ni(C10H9N2O4)2]·3H2O
Mr555.14
Crystal system, space groupTriclinic, P1
Temperature (K)298
a, b, c (Å)9.3787 (12), 10.7935 (14), 11.8795 (15)
α, β, γ (°)86.447 (2), 81.805 (2), 79.847 (2)
V (Å3)1170.8 (3)
Z2
Radiation typeMo Kα
µ (mm−1)0.90
Crystal size (mm)0.32 × 0.27 × 0.14
Data collection
DiffractometerBruker APEXII area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.762, 0.883
No. of measured, independent and
observed [I > 2σ(I)] reflections		5974, 4271, 3173
Rint0.017
(sin θ/λ)max (Å−1)0.597
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.116, 1.03
No. of reflections4271
No. of parameters329
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.41, −0.37

Computer programs: APEX2 (Bruker, 2004), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997), SHELXTL (Bruker, 2001).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O5i0.821.812.606 (3)162.1
O8—H8···O1ii0.821.772.584 (3)170.4
N2—H2···O30.862.022.622 (3)125.9
N2—H2···O11iii0.862.182.826 (4)131.5
N4—H4···O80.861.912.571 (3)132.9
O9—H9A···O100.871.872.741 (6)178.2
O9—H9B···O6iv0.861.982.838 (4)171.0
O10—H10A···O6v0.862.052.882 (5)163.4
O10—H10B···O40.862.162.978 (5)160.3
O11—H11A···O90.861.882.741 (4)172.6
O11—H11B···O2vi0.862.132.890 (4)147.5
Symmetry codes: (i) −x, −y, −z+1; (ii) −x, −y+1, −z+2; (iii) −x+1, −y, −z+1; (iv) x+1, y, z; (v) −x, −y, −z+2; (vi) x+1, y−1, z.
 

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