Diaqua-bis-(1H-imidazole-4-carboxyl-ato-κN,O)zinc.

In the title compound, [Zn(C(4)H(3)N(2)O(2))(2)(H(2)O)(2)], the Zn(II) ion is situated on a twofold rotation axis and exhibits a distorted octa-hedral coordination configuration. The equatorial plane contains two cis-oriented bidentate 1H-imidazole-4-carboxyl-ate ligands and the axial positions are occupied by two coordinated water mol-ecules. In the crystal structure, inter-molecular O-H⋯O and N-H⋯O hydrogen bonds link the mol-ecules into a three-dimensional supra-molecular network. There are π-π inter-actions between the imidazole rings, with a centroid-to-centroid distance of 3.504 (3) Å.

Related literature

For general background, see: Yin et al. (2009 ▶); Zheng et al. (2011) ▶; Alkordi et al. (2009 ▶); Lu et al. (2009 ▶). For related structures, see: Haggag (2005 ▶); Starosta & Leciejewicz (2006 ▶); Gryz et al. (2007 ▶); Yin et al. (2009 ▶).

Experimental

Crystal data

[Zn(C4H3N2O2)2(H2O)2]

M = 323.57

Orthorhombic,

a = 7.1399 (19) Å

b = 11.757 (3) Å

c = 13.508 (4) Å

V = 1133.9 (5) Å3

Z = 4

Mo Kα radiation

μ = 2.20 mm−1

T = 298 K

0.35 × 0.32 × 0.30 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.513, T max = 0.558

5336 measured reflections

1037 independent reflections

913 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.023

wR(F 2) = 0.066

S = 1.08

1037 reflections

95 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.29 e Å−3

Δρmin = −0.33 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811020800/cv5098sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811020800/cv5098Isup2.hkl

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

[Zn(C4H3N2O2)2(H2O)2]	Dx = 1.895 Mg m−3
Mr = 323.57	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pccn	Cell parameters from 2272 reflections
a = 7.1399 (19) Å	θ = 3.3–27.3°
b = 11.757 (3) Å	µ = 2.20 mm−1
c = 13.508 (4) Å	T = 298 K
V = 1133.9 (5) Å3	Block, colourless
Z = 4	0.35 × 0.32 × 0.30 mm
F(000) = 656

Bruker SMART APEXII CCD area-detector diffractometer	1037 independent reflections
Radiation source: fine-focus sealed tube	913 reflections with I > 2σ(I)
graphite	Rint = 0.021
φ and ω scans	θmax = 25.2°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→8
Tmin = 0.513, Tmax = 0.558	k = −8→14
5336 measured reflections	l = −14→16

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)] = 0.023	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.066	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.0338P)2 + 0.618P] where P = (Fo2 + 2Fc2)/3
1037 reflections	(Δ/σ)max < 0.001
95 parameters	Δρmax = 0.29 e Å−3
2 restraints	Δρmin = −0.33 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
Zn1	1.2500	0.7500	0.37215 (2)	0.02665 (15)
N1	1.0565 (2)	0.81059 (14)	0.47393 (11)	0.0263 (4)
N2	0.8608 (2)	0.87069 (15)	0.58685 (12)	0.0318 (4)
H2	0.8123	0.8836	0.6440	0.038*
C2	0.9100 (3)	0.86538 (16)	0.42860 (13)	0.0229 (4)
C1	0.9084 (3)	0.87026 (16)	0.31884 (14)	0.0229 (4)
C3	0.7885 (3)	0.90319 (19)	0.49823 (15)	0.0291 (4)
H3	0.6781	0.9433	0.4875	0.035*
C4	1.0207 (3)	0.81514 (18)	0.56937 (14)	0.0322 (5)
H4	1.0966	0.7838	0.6182	0.039*
O1	1.04760 (19)	0.82909 (12)	0.27495 (9)	0.0304 (3)
O2	0.76821 (19)	0.91520 (13)	0.27745 (10)	0.0303 (4)
O1W	1.0979 (2)	0.59370 (14)	0.34656 (12)	0.0356 (4)
H1WA	1.150 (4)	0.550 (2)	0.3077 (18)	0.062 (9)*
H1WB	0.989 (3)	0.595 (3)	0.328 (2)	0.072 (10)*

	U11	U22	U33	U12	U13	U23
Zn1	0.0242 (2)	0.0358 (2)	0.0200 (2)	0.00824 (13)	0.000	0.000
N1	0.0267 (9)	0.0336 (10)	0.0187 (8)	0.0059 (7)	0.0010 (7)	0.0021 (7)
N2	0.0338 (10)	0.0426 (11)	0.0189 (8)	0.0024 (8)	0.0070 (7)	−0.0012 (7)
C2	0.0220 (10)	0.0252 (10)	0.0214 (10)	0.0008 (8)	0.0003 (8)	0.0002 (8)
C1	0.0246 (10)	0.0238 (10)	0.0205 (9)	−0.0028 (8)	−0.0016 (8)	0.0009 (8)
C3	0.0254 (10)	0.0344 (11)	0.0275 (11)	0.0040 (9)	0.0007 (9)	−0.0018 (9)
C4	0.0344 (12)	0.0421 (13)	0.0203 (10)	0.0044 (9)	−0.0009 (9)	0.0046 (9)
O1	0.0283 (8)	0.0434 (9)	0.0194 (7)	0.0063 (6)	0.0021 (6)	−0.0011 (6)
O2	0.0249 (8)	0.0433 (9)	0.0227 (7)	0.0044 (6)	−0.0045 (6)	0.0051 (6)
O1W	0.0264 (8)	0.0386 (9)	0.0417 (9)	0.0049 (7)	−0.0033 (7)	−0.0108 (7)

Zn1—N1	2.0751 (16)	N2—H2	0.8600
Zn1—N1i	2.0751 (16)	C2—C3	1.354 (3)
Zn1—O1	2.1626 (14)	C2—C1	1.484 (3)
Zn1—O1i	2.1626 (14)	C1—O1	1.255 (2)
Zn1—O1Wi	2.1623 (17)	C1—O2	1.262 (2)
Zn1—O1W	2.1623 (17)	C3—H3	0.9300
N1—C4	1.315 (2)	C4—H4	0.9300
N1—C2	1.373 (2)	O1W—H1WA	0.828 (17)
N2—C4	1.336 (3)	O1W—H1WB	0.818 (18)
N2—C3	1.358 (3)
N1—Zn1—N1i	97.01 (9)	C4—N2—H2	126.1
N1—Zn1—O1	79.04 (6)	C3—N2—H2	126.1
N1i—Zn1—O1	174.10 (5)	C3—C2—N1	109.40 (16)
N1—Zn1—O1i	174.10 (5)	C3—C2—C1	132.55 (17)
N1i—Zn1—O1i	79.04 (6)	N1—C2—C1	118.02 (15)
O1—Zn1—O1i	105.24 (7)	O1—C1—O2	125.47 (17)
N1—Zn1—O1Wi	98.53 (7)	O1—C1—C2	116.81 (15)
N1i—Zn1—O1Wi	93.64 (7)	O2—C1—C2	117.71 (16)
O1—Zn1—O1Wi	82.71 (6)	C2—C3—N2	106.05 (18)
O1i—Zn1—O1Wi	86.15 (6)	C2—C3—H3	127.0
N1—Zn1—O1W	93.64 (7)	N2—C3—H3	127.0
N1i—Zn1—O1W	98.54 (7)	N1—C4—N2	111.05 (18)
O1—Zn1—O1W	86.15 (6)	N1—C4—H4	124.5
O1i—Zn1—O1W	82.71 (6)	N2—C4—H4	124.5
O1Wi—Zn1—O1W	161.60 (9)	C1—O1—Zn1	114.11 (11)
C4—N1—C2	105.65 (16)	Zn1—O1W—H1WA	114 (2)
C4—N1—Zn1	142.45 (15)	Zn1—O1W—H1WB	121 (2)
C2—N1—Zn1	111.89 (12)	H1WA—O1W—H1WB	104 (3)
C4—N2—C3	107.84 (17)
N1i—Zn1—N1—C4	−5.0 (2)	C3—C2—C1—O2	−1.8 (3)
O1—Zn1—N1—C4	179.4 (3)	N1—C2—C1—O2	176.18 (18)
O1i—Zn1—N1—C4	42.6 (7)	N1—C2—C3—N2	−0.3 (2)
O1Wi—Zn1—N1—C4	−99.8 (2)	C1—C2—C3—N2	177.80 (19)
O1W—Zn1—N1—C4	94.1 (3)	C4—N2—C3—C2	0.0 (2)
N1i—Zn1—N1—C2	175.82 (16)	C2—N1—C4—N2	−0.6 (2)
O1—Zn1—N1—C2	0.25 (13)	Zn1—N1—C4—N2	−179.84 (17)
O1i—Zn1—N1—C2	−136.6 (5)	C3—N2—C4—N1	0.4 (3)
O1Wi—Zn1—N1—C2	81.05 (14)	O2—C1—O1—Zn1	−176.15 (15)
O1W—Zn1—N1—C2	−85.11 (14)	C2—C1—O1—Zn1	3.9 (2)
C4—N1—C2—C3	0.6 (2)	N1—Zn1—O1—C1	−2.39 (14)
Zn1—N1—C2—C3	−179.92 (14)	N1i—Zn1—O1—C1	−50.7 (6)
C4—N1—C2—C1	−177.86 (17)	O1i—Zn1—O1—C1	173.43 (15)
Zn1—N1—C2—C1	1.6 (2)	O1Wi—Zn1—O1—C1	−102.60 (14)
C3—C2—C1—O1	178.1 (2)	O1W—Zn1—O1—C1	92.07 (14)
N1—C2—C1—O1	−3.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2ii	0.86	1.93	2.784 (2)	174.
O1W—H1WA···O2iii	0.83 (2)	2.04 (2)	2.850 (2)	167 (3)
O1W—H1WB···O2iv	0.82 (2)	1.96 (2)	2.778 (2)	175 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2i	0.86	1.93	2.784 (2)	174
O1W—H1WA⋯O2ii	0.83 (2)	2.04 (2)	2.850 (2)	167 (3)
O1W—H1WB⋯O2iii	0.82 (2)	1.96 (2)	2.778 (2)	175 (3)

Symmetry codes: (i) ; (ii) ; (iii) .