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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 67| Part 12| December 2011| Pages m1645-m1646
https://doi.org/10.1107/S160053681104387X

Di­aqua­bis­­{5-carb­­oxy-2-[(1H-1,2,4-triazol-1-yl)meth­yl]-1H-imidazole-4-carboxyl­ato}zinc

Jing-Hao Haoa* and Jian-Ling Wanga

aDepartment of Quality Examination and Management, Zhengzhou College of Animal Husbandry Engineering, Zhengzhou, Henan 450011, People's Republic of China
*Correspondence e-mail: zzmzhjh@126.com

(Received 15 October 2011; accepted 22 October 2011; online 2 November 2011)

In the title compound, [Zn(C8H6N5O4)2(H2O)2], the six-coordinate ZnII ion, which is located on an inversion center, has a distorted octa­hedral configuration. Each 5-carb­oxy-2-[(1H-1,2,4-triazol-1-yl)meth­yl]-1H-imidazole-4-carboxyl­ate ligand chelates to the ZnII ion through a triazole N atom and a carboxyl­ate O atom in the equatorial plane. The coordination sphere is completed by two water mol­ecules in axial positions. There is an intra­molecular O—H⋯O hydrogen bond in the ligand. In the crystal, mol­ecules are linked via inter­molecular O—H⋯O, O—H⋯N and N—H⋯N hydrogen bonds, forming a three-dimensional structure.

Related literature

For the assembly of multi-functional ligands with metal ions in the construction of two- and three-dimensional structures with special properties such as electrical conductivity, magnetism, host–guest chemistry, and catalysis, see: Eddaoudi et al. (2001[Eddaoudi, M., Moler, D. B., Li, H., Chen, B., Reineke, T. M., O'Keeffe, M. & Yaghi, O. M. (2001). Acc. Chem. Res. 34, 319-330.]). For metal complexes with N-containing ligands, such as 4,4-bipyridine and triazoles, see: Chang et al. (2010[Chang, H., Fu, M., Zhao, X. J. & Yang, E. C. (2010). J. Coord. Chem. 63, 3551-3564.]). For triazole derivatives complexed to Ru to form anti­tumor metal complexes, see: Komeda et al. (2002[Komeda, S., Lutz, M., Spek, A. L., Yamanaka, Y., Sato, T., Chikuma, M. & Reedijk, J. (2002). J. Am. Chem. Soc. 124, 4738-4746.]). For a silver(I) complex with a ligand containing both a carboxyl­ate and a triazole group, see: Xie et al. (2009[Xie, L. X., Ning, A. M. & Li, X. (2009). J. Coord. Chem. 62, 1604-1612.]). For the isostructural manganese(II) complex of the same ligand, see: Ding & Tong (2010[Ding, D.-G. & Tong, Y. (2010). Acta Cryst. E66, m517.]).

[Scheme 1]

Experimental

Crystal data

  • [Zn(C8H6N5O4)2(H2O)2]

  • Mr = 573.76

  • Monoclinic, P 21 /n

  • a = 7.7020 (15) Å

  • b = 14.678 (3) Å

  • c = 9.2912 (19) Å

  • β = 96.22 (3)°

  • V = 1044.2 (4) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 1.26 mm−1

  • T = 293 K

  • 0.15 × 0.15 × 0.10 mm
Data collection

  • Rigaku Mercury CCD diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2000[Rigaku (2000). CrystalClear. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.834, Tmax = 0.884

  • 8121 measured reflections

  • 2048 independent reflections

  • 1783 reflections with I > 2σ(I)

  • Rint = 0.038
Refinement

  • R[F2 > 2σ(F2)] = 0.045

  • wR(F2) = 0.095

  • S = 1.11

  • 2048 reflections

  • 177 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.31 e Å−3

  • Δρmin = −0.28 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N5—H5A⋯N3i 0.86 1.95 2.801 (4) 170
O3—H3C⋯O2 0.85 1.65 2.493 (3) 173
O5—H5B⋯O4ii 0.73 (5) 2.04 (5) 2.764 (4) 168 (5)
O5—H5C⋯N2iii 0.78 (5) 2.23 (5) 2.896 (4) 143 (5)
Symmetry codes: (i) [x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]; (ii) x, y, z+1; (iii) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: CrystalClear (Rigaku, 2000[Rigaku (2000). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; 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.]); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S160053681104387X/su2331sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681104387X/su2331Isup2.hkl

checkCIF report


Comment top

The assembly of multifunctional ligands with metal ions is currently of great interest due to their use in constructing two- and three-dimensional compounds with special properties (Eddaoudi et al., 2001). So far, most of these multi-dimensional coordination compounds are formed with N-containing ligands, such as, 4,4-bipyridine, polycarboxylic, and triazoles (Chang et al., 2010). Triazole derivatives have been studied as anti-inflammatory drug candidates and have also been used as ligands for binding Pt and Ru to form antitumor metal complexes (Komeda et al., 2002).

A system taking advantage of the presence of both a carboxylate and a triazol group for coordintaion to silver(I) has been reported on by (Xie et al., 2009). The isostructural manganese(II) complex of the title ligand, 2-(1H-1,2,4-triazol-1-yl)methyl]-1H- imidazole-4,5-dicarboxylic acid, has been reported on by (Ding & Tong, 2010). Herein, we report on the synthesis and crystal structure of the title zinc(II) complex.

In the title compound, the zincII atom is located on an inversion center and is six-coordinated, by two imidazole nitrogen atoms (N4 and N4A) and two carboxylate oxygen atoms (O1 and O1A) of two deprotonated 2-((1H-1,2,4-triazol-1-yl)methyl)-1H-imidazole-4,5-dicarboxylic acid ligands, in the equitorial plane, and by two water molecules in axial positions (Fig. 1). The coordination Zn–N bond lengths are 2.110 (2) Å, while the Zn—O bond lengths are 2.115 (2) Å in the equitorial plane and 2.154 (3) Å in axial positions. The coordination geometry around the ZnII ion can be described as distorted octahedral because the O–Zn–N and O–Zn–O coordination angles range from 79.48 (8)° to 100.52 (8)°. There is an intramolecular O—H···O hydrogen bond in each ligand (Table 1). This geometry is very smilar to that in the isostructural manganese(II) complex mentioned above.

In the crystal, molecules are linked via intermolecular O—H···O, O—H···N and N—H···N hydrogen-bonds, to form a three-dimensional structure (Table 1).

Related literature top

For the assembly of multi-functional ligands with metal ions in the construction of two- and three-dimensional compounds with special [special in what way?] properties, see: Eddaoudi et al. (2001). For metal complexes with N-containing ligands, such as 4,4-bipyridine, polycarboxylic, and triazoles, see: Chang et al. (2010). For triazole derivatives complexed with Pt and Ru to form antitumor metal complexes, see: Komeda et al. (2002). For a silver(I) complex with a ligand containing both a carboxylate and a triazole group, see: Xie et al. (2009). For the isostructural manganese(II) complex of the same ligand, see: Ding & Tong (2010).

Experimental top

For the synthesis of title compound, a solution of [2-(1H-1,2,4-triazol-1-yl)methyl]-1H- imidazole-4,5-dicarboxylic acid)(1.0 mmol), Zn(NO3)2.6H2O (0.5 mmol) and NaOH (0.1 mmol) in 10 ml water was stirred for 30 min and then filtered. The filtrate was left to evaporate slowly at room temperature. After two days colourless single crystals, suitable for X-ray analysis, were obtained. Anal. Calcd(%) for C16H16ZnN10O10: C, 33.49; H, 2.81; N, 24.41. Found: C, 33.22; H, 2.60; N, 25.50.

Refinement top

The water H atoms were located in difference Fourier maps and were freely refined. The remaining H atoms were fixed geometrically and treated as riding atoms: O–H = 0.85 Å, N–H = 0.86 Å, and C–H = 0.93 and 0.97 Å for CH and CH2 atoms, respectively, with Uiso(H) = 1.2Ueq(parent O, N, or C atom).

Structure description top

The assembly of multifunctional ligands with metal ions is currently of great interest due to their use in constructing two- and three-dimensional compounds with special properties (Eddaoudi et al., 2001). So far, most of these multi-dimensional coordination compounds are formed with N-containing ligands, such as, 4,4-bipyridine, polycarboxylic, and triazoles (Chang et al., 2010). Triazole derivatives have been studied as anti-inflammatory drug candidates and have also been used as ligands for binding Pt and Ru to form antitumor metal complexes (Komeda et al., 2002).

A system taking advantage of the presence of both a carboxylate and a triazol group for coordintaion to silver(I) has been reported on by (Xie et al., 2009). The isostructural manganese(II) complex of the title ligand, 2-(1H-1,2,4-triazol-1-yl)methyl]-1H- imidazole-4,5-dicarboxylic acid, has been reported on by (Ding & Tong, 2010). Herein, we report on the synthesis and crystal structure of the title zinc(II) complex.

In the title compound, the zincII atom is located on an inversion center and is six-coordinated, by two imidazole nitrogen atoms (N4 and N4A) and two carboxylate oxygen atoms (O1 and O1A) of two deprotonated 2-((1H-1,2,4-triazol-1-yl)methyl)-1H-imidazole-4,5-dicarboxylic acid ligands, in the equitorial plane, and by two water molecules in axial positions (Fig. 1). The coordination Zn–N bond lengths are 2.110 (2) Å, while the Zn—O bond lengths are 2.115 (2) Å in the equitorial plane and 2.154 (3) Å in axial positions. The coordination geometry around the ZnII ion can be described as distorted octahedral because the O–Zn–N and O–Zn–O coordination angles range from 79.48 (8)° to 100.52 (8)°. There is an intramolecular O—H···O hydrogen bond in each ligand (Table 1). This geometry is very smilar to that in the isostructural manganese(II) complex mentioned above.

In the crystal, molecules are linked via intermolecular O—H···O, O—H···N and N—H···N hydrogen-bonds, to form a three-dimensional structure (Table 1).

For the assembly of multi-functional ligands with metal ions in the construction of two- and three-dimensional compounds with special [special in what way?] properties, see: Eddaoudi et al. (2001). For metal complexes with N-containing ligands, such as 4,4-bipyridine, polycarboxylic, and triazoles, see: Chang et al. (2010). For triazole derivatives complexed with Pt and Ru to form antitumor metal complexes, see: Komeda et al. (2002). For a silver(I) complex with a ligand containing both a carboxylate and a triazole group, see: Xie et al. (2009). For the isostructural manganese(II) complex of the same ligand, see: Ding & Tong (2010).

Computing details top

Data collection: CrystalClear (Rigaku, 2000); cell refinement: CrystalClear (Rigaku, 2000); data reduction: CrystalClear (Rigaku, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the crystallographic numbering scheme [symmetry code: (A) 1 - x, 2 - y, 2 - z].
Diaquabis{5-carboxy-2-[(1H-1,2,4-triazol-1-yl)methyl]-1H- imidazole-4-carboxylato}zinc top
Crystal data top
[Zn(C8H6N5O4)2(H2O)2]F(000) = 584
Mr = 573.76Dx = 1.825 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2869 reflections
a = 7.7020 (15) Åθ = 2.2–30.8°
b = 14.678 (3) ŵ = 1.26 mm−1
c = 9.2912 (19) ÅT = 293 K
β = 96.22 (3)°Blocky, colourless
V = 1044.2 (4) Å30.15 × 0.15 × 0.10 mm
Z = 2
Data collection top
Rigaku Mercury CCD
diffractometer		2048 independent reflections
Radiation source: fine-focus sealed tube1783 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.038
ω scansθmax = 26.0°, θmin = 2.6°
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2000)		h = −9→8
Tmin = 0.834, Tmax = 0.884k = −18→18
8121 measured reflectionsl = −11→11
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) = 0.095H atoms treated by a mixture of independent and constrained refinement
S = 1.11 w = 1/[σ2(Fo2) + (0.0395P)2 + 0.6397P]
where P = (Fo2 + 2Fc2)/3
2048 reflections(Δ/σ)max < 0.001
177 parametersΔρmax = 0.31 e Å−3
0 restraintsΔρmin = −0.28 e Å−3
Crystal data top
[Zn(C8H6N5O4)2(H2O)2]V = 1044.2 (4) Å3
Mr = 573.76Z = 2
Monoclinic, P21/nMo Kα radiation
a = 7.7020 (15) ŵ = 1.26 mm−1
b = 14.678 (3) ÅT = 293 K
c = 9.2912 (19) Å0.15 × 0.15 × 0.10 mm
β = 96.22 (3)°
Data collection top
Rigaku Mercury CCD
diffractometer		2048 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2000)		1783 reflections with I > 2σ(I)
Tmin = 0.834, Tmax = 0.884Rint = 0.038
8121 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0450 restraints
wR(F2) = 0.095H atoms treated by a mixture of independent and constrained refinement
S = 1.11Δρmax = 0.31 e Å−3
2048 reflectionsΔρmin = −0.28 e Å−3
177 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
C10.4693 (4)0.6509 (2)0.7392 (3)0.0374 (8)
H10.52210.60680.68670.045*
C20.4094 (4)0.7314 (2)0.9126 (3)0.0335 (7)
H20.40720.75731.00370.040*
C30.1835 (4)0.8324 (2)0.7795 (3)0.0324 (7)
H3A0.14650.84560.87380.039*
H3B0.08160.81310.71640.039*
C40.2560 (4)0.91683 (19)0.7197 (3)0.0238 (6)
C50.4032 (4)1.03992 (19)0.6977 (3)0.0227 (6)
C60.5302 (4)1.1118 (2)0.7490 (3)0.0270 (6)
C70.3112 (4)1.02311 (19)0.5658 (3)0.0223 (6)
C80.2953 (4)1.0733 (2)0.4267 (3)0.0252 (6)
N10.3107 (3)0.75838 (17)0.7936 (3)0.0283 (6)
N20.3478 (3)0.70673 (18)0.6789 (3)0.0352 (6)
N30.5109 (3)0.66274 (18)0.8832 (3)0.0348 (6)
N40.3662 (3)0.97318 (16)0.7941 (2)0.0242 (5)
N50.2194 (3)0.94454 (16)0.5827 (2)0.0250 (5)
H5A0.15050.91780.51680.030*
O10.5950 (3)1.10733 (15)0.8783 (2)0.0345 (5)
O20.5641 (3)1.17290 (14)0.6601 (2)0.0338 (5)
O30.3923 (3)1.14527 (14)0.4209 (2)0.0350 (5)
H3C0.45371.15870.49960.042*
O40.1948 (3)1.04696 (16)0.3247 (2)0.0363 (5)
O50.2866 (4)1.0846 (2)1.0514 (3)0.0512 (8)
H5B0.266 (6)1.082 (3)1.127 (5)0.081 (18)*
H5C0.272 (6)1.133 (3)1.017 (5)0.080 (18)*
Zn10.50001.00001.00000.03113 (18)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0402 (19)0.0351 (19)0.0368 (19)0.0051 (15)0.0033 (15)−0.0006 (14)
C20.0437 (19)0.0294 (17)0.0254 (16)−0.0050 (14)−0.0058 (13)−0.0005 (13)
C30.0290 (16)0.0310 (17)0.0362 (18)−0.0006 (13)−0.0008 (13)0.0056 (13)
C40.0250 (14)0.0256 (15)0.0203 (14)0.0018 (12)0.0004 (11)0.0021 (11)
C50.0253 (15)0.0226 (14)0.0208 (14)0.0033 (12)0.0054 (11)0.0002 (11)
C60.0279 (16)0.0260 (16)0.0273 (16)0.0006 (12)0.0040 (12)−0.0058 (12)
C70.0236 (14)0.0243 (15)0.0189 (14)0.0034 (11)0.0020 (11)0.0014 (11)
C80.0278 (15)0.0261 (15)0.0222 (15)0.0066 (12)0.0050 (12)0.0020 (12)
N10.0325 (14)0.0270 (14)0.0250 (13)−0.0020 (11)0.0004 (10)0.0035 (10)
N20.0417 (15)0.0376 (16)0.0256 (14)0.0011 (13)−0.0005 (11)−0.0016 (11)
N30.0368 (15)0.0339 (15)0.0314 (14)0.0013 (12)−0.0060 (11)0.0046 (11)
N40.0283 (13)0.0260 (13)0.0181 (12)−0.0002 (10)0.0013 (10)0.0006 (9)
N50.0254 (12)0.0279 (14)0.0204 (12)0.0009 (10)−0.0038 (10)−0.0012 (10)
O10.0425 (13)0.0377 (13)0.0225 (11)−0.0097 (10)0.0000 (9)−0.0058 (9)
O20.0404 (12)0.0284 (12)0.0328 (12)−0.0072 (10)0.0050 (9)0.0021 (9)
O30.0446 (13)0.0335 (13)0.0268 (11)−0.0012 (10)0.0026 (10)0.0074 (9)
O40.0393 (13)0.0472 (14)0.0207 (11)0.0009 (10)−0.0044 (9)0.0056 (10)
O50.0620 (18)0.068 (2)0.0239 (14)0.0243 (15)0.0062 (12)0.0123 (13)
Zn10.0372 (3)0.0384 (3)0.0165 (3)−0.0026 (2)−0.0028 (2)0.0000 (2)
Geometric parameters (Å, º) top
C1—N21.322 (4)C6—O21.265 (3)
C1—N31.353 (4)C7—N51.371 (4)
C1—H10.9300C7—C81.482 (4)
C2—N31.322 (4)C8—O41.220 (3)
C2—N11.332 (4)C8—O31.298 (3)
C2—H20.9300N1—N21.363 (3)
C3—N11.459 (4)N4—Zn12.110 (2)
C3—C41.491 (4)N5—H5A0.8600
C3—H3A0.9700O1—Zn12.115 (2)
C3—H3B0.9700O3—H3C0.8500
C4—N41.325 (4)O5—Zn12.154 (3)
C4—N51.337 (3)O5—H5B0.73 (5)
C5—C71.370 (4)O5—H5C0.78 (5)
C5—N41.377 (3)Zn1—N4i2.110 (2)
C5—C61.482 (4)Zn1—O1i2.115 (2)
C6—O11.252 (3)Zn1—O5i2.154 (3)
N2—C1—N3114.9 (3)N2—N1—C3122.6 (2)
N2—C1—H1122.6C1—N2—N1102.2 (2)
N3—C1—H1122.6C2—N3—C1102.7 (3)
N3—C2—N1110.6 (3)C4—N4—C5105.7 (2)
N3—C2—H2124.7C4—N4—Zn1144.30 (19)
N1—C2—H2124.7C5—N4—Zn1109.97 (18)
N1—C3—C4112.2 (2)C4—N5—C7107.9 (2)
N1—C3—H3A109.2C4—N5—H5A126.1
C4—C3—H3A109.2C7—N5—H5A126.1
N1—C3—H3B109.2C6—O1—Zn1115.28 (18)
C4—C3—H3B109.2C8—O3—H3C115.0
H3A—C3—H3B107.9Zn1—O5—H5B115 (4)
N4—C4—N5111.3 (2)Zn1—O5—H5C121 (4)
N4—C4—C3124.7 (2)H5B—O5—H5C114 (5)
N5—C4—C3124.0 (3)N4—Zn1—N4i180.000 (1)
C7—C5—N4109.3 (2)N4—Zn1—O1i100.52 (8)
C7—C5—C6132.5 (3)N4i—Zn1—O1i79.48 (8)
N4—C5—C6118.3 (2)N4—Zn1—O179.48 (8)
O1—C6—O2125.1 (3)N4i—Zn1—O1100.52 (8)
O1—C6—C5116.8 (3)O1i—Zn1—O1180.00 (8)
O2—C6—C5118.1 (3)N4—Zn1—O5i90.04 (10)
C5—C7—N5105.8 (2)N4i—Zn1—O5i89.96 (10)
C5—C7—C8132.6 (3)O1i—Zn1—O5i90.32 (11)
N5—C7—C8121.6 (2)O1—Zn1—O5i89.68 (11)
O4—C8—O3123.1 (3)N4—Zn1—O589.96 (10)
O4—C8—C7120.4 (3)N4i—Zn1—O590.04 (10)
O3—C8—C7116.6 (3)O1i—Zn1—O589.68 (11)
C2—N1—N2109.5 (3)O1—Zn1—O590.32 (11)
C2—N1—C3127.8 (3)O5i—Zn1—O5180.000 (1)
N1—C3—C4—N4−76.1 (4)C3—C4—N4—Zn1−3.2 (5)
N1—C3—C4—N5102.9 (3)C7—C5—N4—C41.0 (3)
C7—C5—C6—O1−178.8 (3)C6—C5—N4—C4−177.7 (2)
N4—C5—C6—O1−0.6 (4)C7—C5—N4—Zn1−178.12 (17)
C7—C5—C6—O21.6 (5)C6—C5—N4—Zn13.2 (3)
N4—C5—C6—O2179.9 (2)N4—C4—N5—C70.3 (3)
N4—C5—C7—N5−0.8 (3)C3—C4—N5—C7−178.8 (3)
C6—C5—C7—N5177.6 (3)C5—C7—N5—C40.3 (3)
N4—C5—C7—C8177.3 (3)C8—C7—N5—C4−178.0 (2)
C6—C5—C7—C8−4.3 (5)O2—C6—O1—Zn1177.0 (2)
C5—C7—C8—O4−175.5 (3)C5—C6—O1—Zn1−2.5 (3)
N5—C7—C8—O42.3 (4)C4—N4—Zn1—N4i−159 (100)
C5—C7—C8—O34.4 (5)C5—N4—Zn1—N4i20 (100)
N5—C7—C8—O3−177.8 (2)C4—N4—Zn1—O1i−1.8 (3)
N3—C2—N1—N2−0.6 (3)C5—N4—Zn1—O1i176.69 (17)
N3—C2—N1—C3−179.2 (3)C4—N4—Zn1—O1178.2 (3)
C4—C3—N1—C299.6 (3)C5—N4—Zn1—O1−3.31 (17)
C4—C3—N1—N2−78.8 (3)C4—N4—Zn1—O5i88.5 (3)
N3—C1—N2—N10.5 (4)C5—N4—Zn1—O5i−93.0 (2)
C2—N1—N2—C10.1 (3)C4—N4—Zn1—O5−91.5 (3)
C3—N1—N2—C1178.8 (3)C5—N4—Zn1—O587.0 (2)
N1—C2—N3—C10.9 (3)C6—O1—Zn1—N43.3 (2)
N2—C1—N3—C2−0.9 (4)C6—O1—Zn1—N4i−176.7 (2)
N5—C4—N4—C5−0.8 (3)C6—O1—Zn1—O1i−136 (100)
C3—C4—N4—C5178.3 (3)C6—O1—Zn1—O5i93.4 (2)
N5—C4—N4—Zn1177.7 (2)C6—O1—Zn1—O5−86.6 (2)
Symmetry code: (i) −x+1, −y+2, −z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N5—H5A···N3ii0.861.952.801 (4)170
O3—H3C···O20.851.652.493 (3)173
O5—H5B···O4iii0.73 (5)2.04 (5)2.764 (4)168 (5)
O5—H5C···N2iv0.78 (5)2.23 (5)2.896 (4)143 (5)
Symmetry codes: (ii) x−1/2, −y+3/2, z−1/2; (iii) x, y, z+1; (iv) −x+1/2, y+1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula[Zn(C8H6N5O4)2(H2O)2]
Mr573.76
Crystal system, space groupMonoclinic, P21/n
Temperature (K)293
a, b, c (Å)7.7020 (15), 14.678 (3), 9.2912 (19)
β (°) 96.22 (3)
V (Å3)1044.2 (4)
Z2
Radiation typeMo Kα
µ (mm−1)1.26
Crystal size (mm)0.15 × 0.15 × 0.10
Data collection
DiffractometerRigaku Mercury CCD
Absorption correctionMulti-scan
(CrystalClear; Rigaku, 2000)
Tmin, Tmax0.834, 0.884
No. of measured, independent and
observed [I > 2σ(I)] reflections		8121, 2048, 1783
Rint0.038
(sin θ/λ)max (Å−1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.095, 1.11
No. of reflections2048
No. of parameters177
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.31, −0.28

Computer programs: CrystalClear (Rigaku, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N5—H5A···N3i0.861.952.801 (4)170
O3—H3C···O20.851.652.493 (3)173
O5—H5B···O4ii0.73 (5)2.04 (5)2.764 (4)168 (5)
O5—H5C···N2iii0.78 (5)2.23 (5)2.896 (4)143 (5)
Symmetry codes: (i) x−1/2, −y+3/2, z−1/2; (ii) x, y, z+1; (iii) −x+1/2, y+1/2, −z+3/2.
 

Acknowledgements

This work was sponsored by the Natural Science Foundation of Henan Province (No. 200510469005).

References

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 First citationRigaku (2000). CrystalClear. Rigaku Corporation, Tokyo, Japan.  Google Scholar
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 First citationXie, L. X., Ning, A. M. & Li, X. (2009). J. Coord. Chem. 62, 1604–1612.  Web of Science CSD CrossRef CAS Google Scholar

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ISSN: 2056-9890
Volume 67| Part 12| December 2011| Pages m1645-m1646
https://doi.org/10.1107/S160053681104387X
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