Diaqua-bis-{5-carb-oxy-2-[(1H-1,2,4-triazol-1-yl)meth-yl]-1H-imidazole-4-carboxyl-ato}zinc.

In the title compound, [Zn(C(8)H(6)N(5)O(4))(2)(H(2)O)(2)], the six-coordinate Zn(II) ion, which is located on an inversion center, has a distorted octa-hedral configuration. Each 5-carb-oxy-2-[(1H-1,2,4-triazol-1-yl)meth-yl]-1H-imidazole-4-carboxyl-ate ligand chelates to the Zn(II) ion through a triazole N atom and a carboxyl-ate O atom in the equatorial plane. The coordination sphere is completed by two water mol-ecules in axial positions. There is an intra-molecular O-H⋯O hydrogen bond in the ligand. In the crystal, mol-ecules are linked via inter-molecular 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 ▶). For metal complexes with N-containing ligands, such as 4,4-bipyridine and triazoles, see: Chang et al. (2010 ▶). For triazole derivatives complexed to 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

Crystal data

[Zn(C8H6N5O4)2(H2O)2]

M = 573.76

Monoclinic,

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 ▶) T min = 0.834, T max = 0.884

8121 measured reflections

2048 independent reflections

1783 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 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

Data collection: CrystalClear (Rigaku, 2000 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681104387X/su2331sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681104387X/su2331Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Zn(C8H6N5O4)2(H2O)2]	F(000) = 584
Mr = 573.76	Dx = 1.825 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2869 reflections
a = 7.7020 (15) Å	θ = 2.2–30.8°
b = 14.678 (3) Å	µ = 1.26 mm−1
c = 9.2912 (19) Å	T = 293 K
β = 96.22 (3)°	Blocky, colourless
V = 1044.2 (4) Å3	0.15 × 0.15 × 0.10 mm
Z = 2

Rigaku Mercury CCD diffractometer	2048 independent reflections
Radiation source: fine-focus sealed tube	1783 reflections with I > 2σ(I)
graphite	Rint = 0.038
ω scans	θmax = 26.0°, θmin = 2.6°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2000)	h = −9→8
Tmin = 0.834, Tmax = 0.884	k = −18→18
8121 measured reflections	l = −11→11

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.095	H 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 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.28 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	0.4693 (4)	0.6509 (2)	0.7392 (3)	0.0374 (8)
H1	0.5221	0.6068	0.6867	0.045*
C2	0.4094 (4)	0.7314 (2)	0.9126 (3)	0.0335 (7)
H2	0.4072	0.7573	1.0037	0.040*
C3	0.1835 (4)	0.8324 (2)	0.7795 (3)	0.0324 (7)
H3A	0.1465	0.8456	0.8738	0.039*
H3B	0.0816	0.8131	0.7164	0.039*
C4	0.2560 (4)	0.91683 (19)	0.7197 (3)	0.0238 (6)
C5	0.4032 (4)	1.03992 (19)	0.6977 (3)	0.0227 (6)
C6	0.5302 (4)	1.1118 (2)	0.7490 (3)	0.0270 (6)
C7	0.3112 (4)	1.02311 (19)	0.5658 (3)	0.0223 (6)
C8	0.2953 (4)	1.0733 (2)	0.4267 (3)	0.0252 (6)
N1	0.3107 (3)	0.75838 (17)	0.7936 (3)	0.0283 (6)
N2	0.3478 (3)	0.70673 (18)	0.6789 (3)	0.0352 (6)
N3	0.5109 (3)	0.66274 (18)	0.8832 (3)	0.0348 (6)
N4	0.3662 (3)	0.97318 (16)	0.7941 (2)	0.0242 (5)
N5	0.2194 (3)	0.94454 (16)	0.5827 (2)	0.0250 (5)
H5A	0.1505	0.9178	0.5168	0.030*
O1	0.5950 (3)	1.10733 (15)	0.8783 (2)	0.0345 (5)
O2	0.5641 (3)	1.17290 (14)	0.6601 (2)	0.0338 (5)
O3	0.3923 (3)	1.14527 (14)	0.4209 (2)	0.0350 (5)
H3C	0.4537	1.1587	0.4996	0.042*
O4	0.1948 (3)	1.04696 (16)	0.3247 (2)	0.0363 (5)
O5	0.2866 (4)	1.0846 (2)	1.0514 (3)	0.0512 (8)
H5B	0.266 (6)	1.082 (3)	1.127 (5)	0.081 (18)*
H5C	0.272 (6)	1.133 (3)	1.017 (5)	0.080 (18)*
Zn1	0.5000	1.0000	1.0000	0.03113 (18)

	U11	U22	U33	U12	U13	U23
C1	0.0402 (19)	0.0351 (19)	0.0368 (19)	0.0051 (15)	0.0033 (15)	−0.0006 (14)
C2	0.0437 (19)	0.0294 (17)	0.0254 (16)	−0.0050 (14)	−0.0058 (13)	−0.0005 (13)
C3	0.0290 (16)	0.0310 (17)	0.0362 (18)	−0.0006 (13)	−0.0008 (13)	0.0056 (13)
C4	0.0250 (14)	0.0256 (15)	0.0203 (14)	0.0018 (12)	0.0004 (11)	0.0021 (11)
C5	0.0253 (15)	0.0226 (14)	0.0208 (14)	0.0033 (12)	0.0054 (11)	0.0002 (11)
C6	0.0279 (16)	0.0260 (16)	0.0273 (16)	0.0006 (12)	0.0040 (12)	−0.0058 (12)
C7	0.0236 (14)	0.0243 (15)	0.0189 (14)	0.0034 (11)	0.0020 (11)	0.0014 (11)
C8	0.0278 (15)	0.0261 (15)	0.0222 (15)	0.0066 (12)	0.0050 (12)	0.0020 (12)
N1	0.0325 (14)	0.0270 (14)	0.0250 (13)	−0.0020 (11)	0.0004 (10)	0.0035 (10)
N2	0.0417 (15)	0.0376 (16)	0.0256 (14)	0.0011 (13)	−0.0005 (11)	−0.0016 (11)
N3	0.0368 (15)	0.0339 (15)	0.0314 (14)	0.0013 (12)	−0.0060 (11)	0.0046 (11)
N4	0.0283 (13)	0.0260 (13)	0.0181 (12)	−0.0002 (10)	0.0013 (10)	0.0006 (9)
N5	0.0254 (12)	0.0279 (14)	0.0204 (12)	0.0009 (10)	−0.0038 (10)	−0.0012 (10)
O1	0.0425 (13)	0.0377 (13)	0.0225 (11)	−0.0097 (10)	0.0000 (9)	−0.0058 (9)
O2	0.0404 (12)	0.0284 (12)	0.0328 (12)	−0.0072 (10)	0.0050 (9)	0.0021 (9)
O3	0.0446 (13)	0.0335 (13)	0.0268 (11)	−0.0012 (10)	0.0026 (10)	0.0074 (9)
O4	0.0393 (13)	0.0472 (14)	0.0207 (11)	0.0009 (10)	−0.0044 (9)	0.0056 (10)
O5	0.0620 (18)	0.068 (2)	0.0239 (14)	0.0243 (15)	0.0062 (12)	0.0123 (13)
Zn1	0.0372 (3)	0.0384 (3)	0.0165 (3)	−0.0026 (2)	−0.0028 (2)	0.0000 (2)

C1—N2	1.322 (4)	C6—O2	1.265 (3)
C1—N3	1.353 (4)	C7—N5	1.371 (4)
C1—H1	0.9300	C7—C8	1.482 (4)
C2—N3	1.322 (4)	C8—O4	1.220 (3)
C2—N1	1.332 (4)	C8—O3	1.298 (3)
C2—H2	0.9300	N1—N2	1.363 (3)
C3—N1	1.459 (4)	N4—Zn1	2.110 (2)
C3—C4	1.491 (4)	N5—H5A	0.8600
C3—H3A	0.9700	O1—Zn1	2.115 (2)
C3—H3B	0.9700	O3—H3C	0.8500
C4—N4	1.325 (4)	O5—Zn1	2.154 (3)
C4—N5	1.337 (3)	O5—H5B	0.73 (5)
C5—C7	1.370 (4)	O5—H5C	0.78 (5)
C5—N4	1.377 (3)	Zn1—N4i	2.110 (2)
C5—C6	1.482 (4)	Zn1—O1i	2.115 (2)
C6—O1	1.252 (3)	Zn1—O5i	2.154 (3)
N2—C1—N3	114.9 (3)	N2—N1—C3	122.6 (2)
N2—C1—H1	122.6	C1—N2—N1	102.2 (2)
N3—C1—H1	122.6	C2—N3—C1	102.7 (3)
N3—C2—N1	110.6 (3)	C4—N4—C5	105.7 (2)
N3—C2—H2	124.7	C4—N4—Zn1	144.30 (19)
N1—C2—H2	124.7	C5—N4—Zn1	109.97 (18)
N1—C3—C4	112.2 (2)	C4—N5—C7	107.9 (2)
N1—C3—H3A	109.2	C4—N5—H5A	126.1
C4—C3—H3A	109.2	C7—N5—H5A	126.1
N1—C3—H3B	109.2	C6—O1—Zn1	115.28 (18)
C4—C3—H3B	109.2	C8—O3—H3C	115.0
H3A—C3—H3B	107.9	Zn1—O5—H5B	115 (4)
N4—C4—N5	111.3 (2)	Zn1—O5—H5C	121 (4)
N4—C4—C3	124.7 (2)	H5B—O5—H5C	114 (5)
N5—C4—C3	124.0 (3)	N4—Zn1—N4i	180.000 (1)
C7—C5—N4	109.3 (2)	N4—Zn1—O1i	100.52 (8)
C7—C5—C6	132.5 (3)	N4i—Zn1—O1i	79.48 (8)
N4—C5—C6	118.3 (2)	N4—Zn1—O1	79.48 (8)
O1—C6—O2	125.1 (3)	N4i—Zn1—O1	100.52 (8)
O1—C6—C5	116.8 (3)	O1i—Zn1—O1	180.00 (8)
O2—C6—C5	118.1 (3)	N4—Zn1—O5i	90.04 (10)
C5—C7—N5	105.8 (2)	N4i—Zn1—O5i	89.96 (10)
C5—C7—C8	132.6 (3)	O1i—Zn1—O5i	90.32 (11)
N5—C7—C8	121.6 (2)	O1—Zn1—O5i	89.68 (11)
O4—C8—O3	123.1 (3)	N4—Zn1—O5	89.96 (10)
O4—C8—C7	120.4 (3)	N4i—Zn1—O5	90.04 (10)
O3—C8—C7	116.6 (3)	O1i—Zn1—O5	89.68 (11)
C2—N1—N2	109.5 (3)	O1—Zn1—O5	90.32 (11)
C2—N1—C3	127.8 (3)	O5i—Zn1—O5	180.000 (1)
N1—C3—C4—N4	−76.1 (4)	C3—C4—N4—Zn1	−3.2 (5)
N1—C3—C4—N5	102.9 (3)	C7—C5—N4—C4	1.0 (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—O2	1.6 (5)	C6—C5—N4—Zn1	3.2 (3)
N4—C5—C6—O2	179.9 (2)	N4—C4—N5—C7	0.3 (3)
N4—C5—C7—N5	−0.8 (3)	C3—C4—N5—C7	−178.8 (3)
C6—C5—C7—N5	177.6 (3)	C5—C7—N5—C4	0.3 (3)
N4—C5—C7—C8	177.3 (3)	C8—C7—N5—C4	−178.0 (2)
C6—C5—C7—C8	−4.3 (5)	O2—C6—O1—Zn1	177.0 (2)
C5—C7—C8—O4	−175.5 (3)	C5—C6—O1—Zn1	−2.5 (3)
N5—C7—C8—O4	2.3 (4)	C4—N4—Zn1—N4i	−159 (100)
C5—C7—C8—O3	4.4 (5)	C5—N4—Zn1—N4i	20 (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—O1i	176.69 (17)
N3—C2—N1—C3	−179.2 (3)	C4—N4—Zn1—O1	178.2 (3)
C4—C3—N1—C2	99.6 (3)	C5—N4—Zn1—O1	−3.31 (17)
C4—C3—N1—N2	−78.8 (3)	C4—N4—Zn1—O5i	88.5 (3)
N3—C1—N2—N1	0.5 (4)	C5—N4—Zn1—O5i	−93.0 (2)
C2—N1—N2—C1	0.1 (3)	C4—N4—Zn1—O5	−91.5 (3)
C3—N1—N2—C1	178.8 (3)	C5—N4—Zn1—O5	87.0 (2)
N1—C2—N3—C1	0.9 (3)	C6—O1—Zn1—N4	3.3 (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—C5	178.3 (3)	C6—O1—Zn1—O5i	93.4 (2)
N5—C4—N4—Zn1	177.7 (2)	C6—O1—Zn1—O5	−86.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5A···N3ii	0.86	1.95	2.801 (4)	170
O3—H3C···O2	0.85	1.65	2.493 (3)	173
O5—H5B···O4iii	0.73 (5)	2.04 (5)	2.764 (4)	168 (5)
O5—H5C···N2iv	0.78 (5)	2.23 (5)	2.896 (4)	143 (5)

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) ; (ii) ; (iii) .