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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 10| October 2012| Pages m1286-m1287
https://doi.org/10.1107/S1600536812038895

Poly[di­aqua­[μ-1,4-bis­­(1H-imidazol-1-yl)benzene-κ2N3:N3′](μ-fumarato-κ2O1:O4)nickel(II)]

Chang-Xin Bian,a Xiao-Qiang Yaoa and Yu-Min Songa*

aCollege of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070, People's Republic of China
*Correspondence e-mail: songym@nwnu.edu.cn

(Received 18 July 2012; accepted 11 September 2012; online 22 September 2012)

In the title compound, [Ni(C4H2O4)(C12H10N4)(H2O)2]n, the NiII ion has a distorted octa­hedral coordination geometry. The asymmetric unit is composed of an Ni2+ ion, located on a twofold rotation axis, one half of a 1,4-bis­(1H-imidazol-1-yl)benzene (BIMB) ligand and one half of a fumarte (fum2−) dianion, both ligands being located about inversion centers, and a coordinating water mol­ecule. The NiII ions are linked by two BIMB ligands and two fum2− dianions, forming a four-connected layered structure parallel to (010) with a 44-sql topology. Within each layer, there are rhombic grids with dimensions of ca 13.5 × 9.0 Å and approximate angles of 109 and 70°. The crystal packing features a two-dimensional → two-dimensional parallel/parallel interpenetration in which one undulating layer is catenated to another equivalent one, forming a new bilayer. Moreover, the entangled two-dimensional layers are connected by O—H⋯O and C—H⋯O hydrogen bonds, generating a three-dimensional structure.

Related literature

For multi-dimensional coordination polymers and their applications, see: Batten & Robson (1998[Batten, S. R. & Robson, R. (1998). Angew. Chem. Int. Ed. 37, 1460-1494.]); Carlucci et al. (2003a[Carlucci, L., Ciani, G. & Proserpio, D. M. (2003a). Coord. Chem. Rev. 246, 247-289.],b[Carlucci, L., Ciani, G. & Proserpio, D. M. (2003b). CrystEngComm, 5, 269-279.]); Moulton & Zaworotko (2001[Moulton, B. & Zaworotko, M. J. (2001). Chem. Rev. 101, 1629-1658.]); Sun et al. (2006[Sun, D. F., Ma, S. Q., Ke, Y. X., Collins, D. J. & Zhou, H. C. (2006). J. Am. Chem. Soc. 128, 3896-3897.]); Wu et al. (2011[Wu, H., Liu, H. Y., Liu, B., Yang, J., Liu, Y. Y., Ma, J. F., Liu, Y. Y. & Bai, H. Y. (2011). CrystEngComm, 13, 3402-3407.]); Bu et al. (2004[Bu, X. H., Tong, M. L., Chang, H. C., Kitagawa, S. & Batten, S. R. (2004). Angew. Chem. Int. Ed. 43, 192-195.]). For their potential applications in electron transfer and drug delivery, see: Harriman & Sauvage (1996[Harriman, A. & Sauvage, J. P. (1996). Chem. Soc. Rev. pp. 41-48.]); Raymo & Sauvage (1999[Raymo, F. M. & Sauvage, J. P. (1999). Chem. Rev. 99, 1643-1664.]). For the structures of some related compounds, see: Chen et al. (2010[Chen, S. S., Bai, Z. S., Fan, J., Lv, G. C., Su, Z., Chen, M. S. & Sun, W. Y. (2010). CrystEngComm, 12, 3091-3104.]); Li et al. (2012[Li, Y. W., Ma, H., Chen, Y. Q., He, K. H., Li, Z. X. & Bu, X. H. (2012). Cryst. Growth Des. 12, 189-196.]); Bu et al. (2004[Bu, X. H., Tong, M. L., Chang, H. C., Kitagawa, S. & Batten, S. R. (2004). Angew. Chem. Int. Ed. 43, 192-195.]).

[Scheme 1]

Experimental

Crystal data

  • [Ni(C4H2O4)(C12H10N4)(H2O)2]

  • Mr = 419.04

  • Orthorhombic, P b c n

  • a = 11.2806 (4) Å

  • b = 16.3703 (7) Å

  • c = 9.0253 (3) Å

  • V = 1666.67 (11) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 1.21 mm−1

  • T = 296 K

  • 0.23 × 0.22 × 0.20 mm
Data collection

  • Bruke APEXII CCD area-dector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.768, Tmax = 0.794

  • 8512 measured reflections

  • 2108 independent reflections

  • 1827 reflections with I > 2σ(I)

  • Rint = 0.019
Refinement

  • R[F2 > 2σ(F2)] = 0.030

  • wR(F2) = 0.093

  • S = 1.08

  • 2108 reflections

  • 123 parameters

  • 2 restraints

  • H-atom parameters constrained

  • Δρmax = 0.36 e Å−3

  • Δρmin = −0.48 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O3—H3Y⋯O2i 0.85 1.96 2.7033 (18) 146
O3—H3X⋯O2ii 0.85 2.03 2.8361 (18) 159
C3—H3⋯O2ii 0.93 2.49 3.360 (2) 155
Symmetry codes: (i) [-x+2, y, -z+{\script{3\over 2}}]; (ii) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1].

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2003[Bruker (2003). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and DIAMOND (Brandenburg, 2010[Brandenburg, K. (2010). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXTL and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812038895/su2481sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812038895/su2481Isup2.hkl

checkCIF report


Comment top

Entanglement, one of the ubiquitous phenomena in nature, has received considerable attention due to their intrinsic aesthetic architectures (Bu et al., 2004; Carlucci et al., 2003a; Wu et al., 2011) and potential applications (Sun et al., 2006; Moulton & Zaworotko, 2001). Many structurally interesting entangled structures, such as polyrotaxane, polycatenation, polythreading, have been discussed in detail by (Batten et al., 1998; Carlucci et al., 2003b). Polycatenation as a type of interesting networks of entangled systems has attracted much attention for their potential application in energy of electron transfer and drug delivery (Harriman & Sauvage, 1996; Raymo & Sauvage, 1999). Herein, we report on the crystal structure of a NiII coordination polymer built from linear BIMB and fum2- ligands, which features a two-dimensional → two-dimensional parallel/parallel polycatenation network.

The asymmetric unit of the title compound contains half a NiII ion located on a two-fold rotation axis, half a fum2- dianion and half a BIMB ligand both located about inversion centers, and a coordinated water molecule. Each NiII ion is coordinated by two water molecules, two different carboxylate O atoms from two different fum2- dianions and by two N atoms from two different BIMB ligands, and has a distorted octahedral geometry (Fig. 1).

It is interesting to note that the maleic acid (hydrolysis product of maleic anhydride) is converted into fumaric acid on the self-assembly of the title compound. This is probably because trans-fumaric has a higher thermal stability than cis-maleic acid.

In the crystal, each NiII ion is connected by two BIMB ligands and two fum2- ligands to form an infinite two-dimensional puckered sheet with rhombic grids (Fig. 2). Within each layer, the rhombic grids have dimensions of ca. 13.5 Å × 9.0 Å with angles of of ca. 109.60 and 70.40° (defined by Ni···Ni distances and Ni···Ni···Ni angles). The large size of the grids in two adjacent layers allow a two-dimensional → two-dimensional parallel/parallel polycatenation to occur (Fig. 3). From a topological perspective, each NiII ion can be regarded as a four-connected node, thus this two-dimensional network can be assigned to the 44-sql topology.

Moreover, the entangled two-dimensional layers are further connected by O–H···O hydrogen bonds to generate a three-dimensional structure (Fig. 4).

The structure of a similar NiII coordination polymer assembled by BIMB ligand and adipic acid has been described by (Chen et al., 2010). However, compared with the title compound, the adipic acid is a longer spacer length and more flexible, and crystallizes in the lower symmetry triclinic space group P1 rather than orthorhombic space group Pbcn for the title compound with the short fumarate spacer.

Another relevant example reported by (Bu et al., 2004) is a ZnII coordination polymer (Li et al. 2012). Like the title complex, it is also built from BIMB and fum2- ligands. However, the difference in the metal center results in an interesting 5-fold interpenetrated three-dimensional framework based on a diamondoid topology.

In summary, we have synthesized a NiII coordination polymer by the hydrothermal reaction of Ni(NO3)2 with H2fum and BIMB ligands, which features a two-dimensional → two-dimensional parallel/parallel polycatenation network. On comparing with two relevant complexes based on the BIMB ligand, we found that the coordination geometry of the central metal ions and the flexibility of the auxiliary carboxylate ligands indeed have a significant effect on the architecture of the target complexes.

Related literature top

For multi-dimensional coordination polymers and their applications, see: Batten & Robson (1998); Carlucci et al. (2003a,b); Moulton & Zaworotko (2001); Sun et al. (2006); Wu et al. (2011); Bu et al. (2004). For their potential applications in electron transfer and drug delivery, see: Harriman & Sauvage (1996); Raymo & Sauvage (1999). For the structures of some related compounds, see: Chen et al. (2010); Li et al. (2012); Bu et al. (2004).

Experimental top

A mixture of 1,4-Bis(1-imidazolyl)benzene (BIMB) (0.032 g, 0.15 mmol), maleic anydride (0.015 g, 0.15 mmol) and Ni(NO3)2 (0.045 g, 0.25 mmol) in N,N'-dimethylformamide (DMF) (4 ml) and H2O (2 ml) was placed in a Teflon-lined stainless steel vessel and heated at 363 K for 3 days. On cooling to room temperature green block-like single crystals suitable for X-ray diffraction were obtained [70% yield (based on BIMB ligand)]. Anal. Calcd for C16H16N4O6Ni: C, 45.86; H, 3.85; N, 13.37%. Found: C, 45.93; H, 3.87; N, 13.41%. Spectroscopic data for the title compound are given in the archived CIF.

Refinement top

The water H atoms were located in a difference Fourier map and included as riding atoms, with O—H = 0.85 and Uiso(H) = 1.5Ueq(O). The C-bound H atoms were placed in calculated positions and treated as riding: C—H = 0.93 Å with Uiso(H) = 1.2Ueq(C).

Structure description top

Entanglement, one of the ubiquitous phenomena in nature, has received considerable attention due to their intrinsic aesthetic architectures (Bu et al., 2004; Carlucci et al., 2003a; Wu et al., 2011) and potential applications (Sun et al., 2006; Moulton & Zaworotko, 2001). Many structurally interesting entangled structures, such as polyrotaxane, polycatenation, polythreading, have been discussed in detail by (Batten et al., 1998; Carlucci et al., 2003b). Polycatenation as a type of interesting networks of entangled systems has attracted much attention for their potential application in energy of electron transfer and drug delivery (Harriman & Sauvage, 1996; Raymo & Sauvage, 1999). Herein, we report on the crystal structure of a NiII coordination polymer built from linear BIMB and fum2- ligands, which features a two-dimensional → two-dimensional parallel/parallel polycatenation network.

The asymmetric unit of the title compound contains half a NiII ion located on a two-fold rotation axis, half a fum2- dianion and half a BIMB ligand both located about inversion centers, and a coordinated water molecule. Each NiII ion is coordinated by two water molecules, two different carboxylate O atoms from two different fum2- dianions and by two N atoms from two different BIMB ligands, and has a distorted octahedral geometry (Fig. 1).

It is interesting to note that the maleic acid (hydrolysis product of maleic anhydride) is converted into fumaric acid on the self-assembly of the title compound. This is probably because trans-fumaric has a higher thermal stability than cis-maleic acid.

In the crystal, each NiII ion is connected by two BIMB ligands and two fum2- ligands to form an infinite two-dimensional puckered sheet with rhombic grids (Fig. 2). Within each layer, the rhombic grids have dimensions of ca. 13.5 Å × 9.0 Å with angles of of ca. 109.60 and 70.40° (defined by Ni···Ni distances and Ni···Ni···Ni angles). The large size of the grids in two adjacent layers allow a two-dimensional → two-dimensional parallel/parallel polycatenation to occur (Fig. 3). From a topological perspective, each NiII ion can be regarded as a four-connected node, thus this two-dimensional network can be assigned to the 44-sql topology.

Moreover, the entangled two-dimensional layers are further connected by O–H···O hydrogen bonds to generate a three-dimensional structure (Fig. 4).

The structure of a similar NiII coordination polymer assembled by BIMB ligand and adipic acid has been described by (Chen et al., 2010). However, compared with the title compound, the adipic acid is a longer spacer length and more flexible, and crystallizes in the lower symmetry triclinic space group P1 rather than orthorhombic space group Pbcn for the title compound with the short fumarate spacer.

Another relevant example reported by (Bu et al., 2004) is a ZnII coordination polymer (Li et al. 2012). Like the title complex, it is also built from BIMB and fum2- ligands. However, the difference in the metal center results in an interesting 5-fold interpenetrated three-dimensional framework based on a diamondoid topology.

In summary, we have synthesized a NiII coordination polymer by the hydrothermal reaction of Ni(NO3)2 with H2fum and BIMB ligands, which features a two-dimensional → two-dimensional parallel/parallel polycatenation network. On comparing with two relevant complexes based on the BIMB ligand, we found that the coordination geometry of the central metal ions and the flexibility of the auxiliary carboxylate ligands indeed have a significant effect on the architecture of the target complexes.

For multi-dimensional coordination polymers and their applications, see: Batten & Robson (1998); Carlucci et al. (2003a,b); Moulton & Zaworotko (2001); Sun et al. (2006); Wu et al. (2011); Bu et al. (2004). For their potential applications in electron transfer and drug delivery, see: Harriman & Sauvage (1996); Raymo & Sauvage (1999). For the structures of some related compounds, see: Chen et al. (2010); Li et al. (2012); Bu et al. (2004).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 2010); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, with atom numbering. The displacement ellipsoids are drawn at the 50% probability level [H atoms have been omitted for clarity; symmetry codes: (i) 1 – x, y, 0.5 – z; (ii) 1 – x, y, -0.5 – z; (iii) 2 – x, –y, –z].
[Figure 2] Fig. 2. A view of the two-dimensional undulated 44-sql layer of the title compound.
[Figure 3] Fig. 3. A view of the two-fold parallel polycatenation of the two-dimensional layers in the crystal structure of the title compound.
[Figure 4] Fig. 4. A view of the entangled two-dimensional layers that extended to a three-dimensional structure via O–H···O hydrogen bonds in the crystal structure of the title compound.
Poly[diaqua[µ-1,4-bis(1H-imidazol-1-yl)benzene- κ2N3:N3'](µ-fumarato- κ2O1:O4)nickel(II)] top
Crystal data top
[Ni(C4H2O4)(C12H10N4)(H2O)2]F(000) = 864
Mr = 419.04Dx = 1.670 Mg m−3
Orthorhombic, PbcnMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2abCell parameters from 4217 reflections
a = 11.2806 (4) Åθ = 2.5–28.4°
b = 16.3703 (7) ŵ = 1.21 mm−1
c = 9.0253 (3) ÅT = 296 K
V = 1666.67 (11) Å3Block, green
Z = 40.23 × 0.22 × 0.20 mm
Data collection top
Bruke APEXII CCD area-dector
diffractometer		2108 independent reflections
Radiation source: fine-focus sealed tube1827 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.019
CCD rotation images, thin slices scansθmax = 28.5°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −13→15
Tmin = 0.768, Tmax = 0.794k = −18→21
8512 measured reflectionsl = −12→12
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)] = 0.030Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.093H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.047P)2 + 1.0911P]
where P = (Fo2 + 2Fc2)/3
2108 reflections(Δ/σ)max < 0.001
123 parametersΔρmax = 0.36 e Å−3
2 restraintsΔρmin = −0.48 e Å−3
Crystal data top
[Ni(C4H2O4)(C12H10N4)(H2O)2]V = 1666.67 (11) Å3
Mr = 419.04Z = 4
Orthorhombic, PbcnMo Kα radiation
a = 11.2806 (4) ŵ = 1.21 mm−1
b = 16.3703 (7) ÅT = 296 K
c = 9.0253 (3) Å0.23 × 0.22 × 0.20 mm
Data collection top
Bruke APEXII CCD area-dector
diffractometer		2108 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		1827 reflections with I > 2σ(I)
Tmin = 0.768, Tmax = 0.794Rint = 0.019
8512 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0302 restraints
wR(F2) = 0.093H-atom parameters constrained
S = 1.08Δρmax = 0.36 e Å−3
2108 reflectionsΔρmin = −0.48 e Å−3
123 parameters
Special details top

Experimental. Spectroscopic data for the title compound :

IR (KBr, cm-1): 3380m, 3133m, 1564s, 1533s, 1385s, 1307w, 1269w, 1130w, 1195w, 1074m, 970w, 880w, 829m, 751m, 682w, 656w, 534w, 495w.

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
C10.85967 (16)0.48653 (12)0.8087 (2)0.0337 (4)
H10.91270.50690.87850.040*
C20.76108 (18)0.52549 (13)0.7609 (2)0.0353 (4)
H20.73440.57680.78990.042*
C30.77741 (16)0.40688 (11)0.6505 (2)0.0294 (4)
H30.76160.36270.58890.035*
C40.57558 (18)0.56487 (12)0.5293 (3)0.0409 (5)
H40.62660.60820.54870.049*
C50.60153 (15)0.48748 (11)0.5802 (2)0.0290 (4)
C60.52718 (19)0.42289 (12)0.5509 (3)0.0408 (5)
H60.54610.37090.58510.049*
C71.08521 (15)0.29993 (11)0.43626 (19)0.0266 (3)
C81.05530 (18)0.30159 (14)0.2748 (2)0.0348 (4)
H81.11690.30270.20640.042*
N10.86960 (13)0.41195 (10)0.73829 (16)0.0261 (3)
N20.70833 (13)0.47384 (9)0.66080 (18)0.0288 (3)
Ni11.00000.323481 (18)0.75000.01981 (12)
O11.00329 (10)0.31848 (9)0.52371 (16)0.0310 (3)
O21.18776 (11)0.27709 (9)0.47076 (14)0.0347 (3)
O30.86671 (12)0.23178 (8)0.74938 (13)0.0291 (3)
H3Y0.82140.23830.82370.044*
H3X0.82640.23560.67010.044*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0277 (8)0.0378 (10)0.0358 (10)0.0029 (7)−0.0078 (8)−0.0101 (8)
C20.0317 (9)0.0328 (9)0.0414 (11)0.0050 (8)−0.0073 (8)−0.0121 (8)
C30.0260 (8)0.0294 (9)0.0327 (9)0.0065 (7)−0.0078 (7)−0.0043 (7)
C40.0341 (10)0.0268 (9)0.0617 (14)0.0004 (7)−0.0200 (10)−0.0014 (9)
C50.0221 (8)0.0304 (9)0.0344 (9)0.0059 (6)−0.0081 (7)−0.0022 (7)
C60.0358 (10)0.0244 (8)0.0621 (14)0.0050 (7)−0.0197 (10)0.0031 (9)
C70.0272 (8)0.0337 (9)0.0189 (7)0.0008 (7)−0.0008 (6)−0.0015 (7)
C80.0321 (10)0.0489 (11)0.0233 (8)0.0010 (9)0.0014 (7)0.0001 (8)
N10.0212 (7)0.0307 (8)0.0266 (7)0.0027 (6)−0.0046 (5)−0.0025 (6)
N20.0230 (7)0.0287 (7)0.0346 (8)0.0049 (6)−0.0086 (6)−0.0031 (6)
Ni10.01593 (17)0.02772 (18)0.01579 (17)0.000−0.00177 (9)0.000
O10.0255 (6)0.0512 (9)0.0164 (6)0.0054 (5)−0.0009 (4)−0.0025 (5)
O20.0270 (6)0.0532 (8)0.0238 (6)0.0093 (6)0.0004 (5)−0.0013 (6)
O30.0263 (6)0.0357 (7)0.0253 (7)−0.0042 (5)−0.0021 (5)−0.0035 (5)
Geometric parameters (Å, º) top
C1—C21.353 (3)C6—H60.9300
C1—N11.381 (2)C7—O11.253 (2)
C1—H10.9300C7—O21.255 (2)
C2—N21.373 (2)C7—C81.496 (3)
C2—H20.9300C8—C8ii1.326 (4)
C3—N11.310 (2)C8—H80.9300
C3—N21.348 (2)N1—Ni12.0670 (15)
C3—H30.9300Ni1—O12.0443 (15)
C4—C51.379 (3)Ni1—O1iii2.0443 (15)
C4—C6i1.381 (3)Ni1—N1iii2.0671 (15)
C4—H40.9300Ni1—O3iii2.1247 (13)
C5—C61.375 (3)Ni1—O32.1247 (13)
C5—N21.425 (2)O3—H3Y0.8500
C6—C4i1.381 (3)O3—H3X0.8501
C2—C1—N1109.66 (16)C3—N1—Ni1123.47 (13)
C2—C1—H1125.2C1—N1—Ni1130.81 (12)
N1—C1—H1125.2C3—N2—C2107.19 (15)
C1—C2—N2106.02 (17)C3—N2—C5125.53 (15)
C1—C2—H2127.0C2—N2—C5127.28 (15)
N2—C2—H2127.0O1—Ni1—O1iii175.41 (8)
N1—C3—N2111.46 (16)O1—Ni1—N189.42 (5)
N1—C3—H3124.3O1iii—Ni1—N193.80 (5)
N2—C3—H3124.3O1—Ni1—N1iii93.79 (5)
C5—C4—C6i119.07 (18)O1iii—Ni1—N1iii89.42 (5)
C5—C4—H4120.5N1—Ni1—N1iii91.04 (9)
C6i—C4—H4120.5O1—Ni1—O3iii87.80 (5)
C6—C5—C4120.85 (16)O1iii—Ni1—O3iii88.96 (5)
C6—C5—N2119.55 (16)N1—Ni1—O3iii177.19 (5)
C4—C5—N2119.57 (16)N1iii—Ni1—O3iii89.51 (6)
C5—C6—C4i120.07 (18)O1—Ni1—O388.96 (5)
C5—C6—H6120.0O1iii—Ni1—O387.79 (5)
C4i—C6—H6120.0N1—Ni1—O389.50 (6)
O1—C7—O2126.58 (16)N1iii—Ni1—O3177.19 (5)
O1—C7—C8116.29 (16)O3iii—Ni1—O390.09 (8)
O2—C7—C8117.06 (16)C7—O1—Ni1130.74 (12)
C8ii—C8—C7122.8 (2)Ni1—O3—H3Y109.6
C8ii—C8—H8118.6Ni1—O3—H3X109.3
C7—C8—H8118.6H3Y—O3—H3X109.5
C3—N1—C1105.67 (15)
N1—C1—C2—N20.8 (2)C4—C5—N2—C236.9 (3)
C6i—C4—C5—C60.6 (4)C3—N1—Ni1—O145.30 (16)
C6i—C4—C5—N2178.9 (2)C1—N1—Ni1—O1−131.70 (17)
C4—C5—C6—C4i−0.6 (4)C3—N1—Ni1—O1iii−131.42 (15)
N2—C5—C6—C4i−178.9 (2)C1—N1—Ni1—O1iii51.58 (17)
O1—C7—C8—C8ii−16.9 (2)C3—N1—Ni1—N1iii139.09 (17)
O2—C7—C8—C8ii160.34 (12)C1—N1—Ni1—N1iii−37.91 (15)
N2—C3—N1—C1−0.2 (2)C3—N1—Ni1—O3iii38.0 (12)
N2—C3—N1—Ni1−177.88 (12)C1—N1—Ni1—O3iii−139.0 (10)
C2—C1—N1—C3−0.4 (2)C3—N1—Ni1—O3−43.66 (15)
C2—C1—N1—Ni1177.04 (15)C1—N1—Ni1—O3139.33 (17)
N1—C3—N2—C20.7 (2)O2—C7—O1—Ni12.1 (3)
N1—C3—N2—C5−179.97 (17)C8—C7—O1—Ni1179.05 (13)
C1—C2—N2—C3−0.9 (2)O1iii—Ni1—O1—C7−73.40 (17)
C1—C2—N2—C5179.80 (19)N1—Ni1—O1—C7152.04 (17)
C6—C5—N2—C336.0 (3)N1iii—Ni1—O1—C761.04 (17)
C4—C5—N2—C3−142.3 (2)O3iii—Ni1—O1—C7−28.32 (17)
C6—C5—N2—C2−144.8 (2)O3—Ni1—O1—C7−118.44 (17)
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+2, y, −z+1/2; (iii) −x+2, y, −z+3/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3Y···O2iii0.851.962.7033 (18)146
O3—H3X···O2iv0.852.032.8361 (18)159
C3—H3···O2iv0.932.493.360 (2)155
Symmetry codes: (iii) −x+2, y, −z+3/2; (iv) x−1/2, −y+1/2, −z+1.

Experimental details

Crystal data
Chemical formula[Ni(C4H2O4)(C12H10N4)(H2O)2]
Mr419.04
Crystal system, space groupOrthorhombic, Pbcn
Temperature (K)296
a, b, c (Å)11.2806 (4), 16.3703 (7), 9.0253 (3)
V (Å3)1666.67 (11)
Z4
Radiation typeMo Kα
µ (mm−1)1.21
Crystal size (mm)0.23 × 0.22 × 0.20
Data collection
DiffractometerBruke APEXII CCD area-dector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.768, 0.794
No. of measured, independent and
observed [I > 2σ(I)] reflections		8512, 2108, 1827
Rint0.019
(sin θ/λ)max (Å−1)0.670
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.030, 0.093, 1.08
No. of reflections2108
No. of parameters123
No. of restraints2
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.36, −0.48

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 2010), SHELXTL (Sheldrick, 2008) and publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3Y···O2i0.851.962.7033 (18)146
O3—H3X···O2ii0.852.032.8361 (18)159
C3—H3···O2ii0.932.493.360 (2)155
Symmetry codes: (i) −x+2, y, −z+3/2; (ii) x−1/2, −y+1/2, −z+1.
 

Acknowledgements

This work was supported financially by the Key Laboratory of Eco-Environment-Related Polymer Materials (Northwest Normal University) and the Ministry of Education of Gansu (No. 1101–05).

References

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ISSN: 2056-9890
Volume 68| Part 10| October 2012| Pages m1286-m1287
https://doi.org/10.1107/S1600536812038895
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