Poly[bis-[μ(2)-2-(1H-1,2,4-triazol-1-yl)acetato]zinc(II)].

In the title compound, [Zn(C(4)H(4)N(3)O(2))(2)](n), the Zn(II) atom is coordinated by two O atoms [Zn-O = 1.969 (2) and 1.997 (2) Å] and two N atoms [Zn-N = 2.046 (2) and 2.001 (2) Å] in a distorted tetra-hedral geometry. Non-classical inter-molecular C-H⋯O hydrogen bonds link the complex into a three-dimensional supra-molecular framework.

Related literature

For related structures, see: Dixon et al. (2000 ▶); Fujita et al. (1998 ▶); Ouellette et al. (2006 ▶); Xie et al. (2009 ▶); Zhou et al. (2009 ▶). For the preparation of 2-(1H-1,2,4-triazol-1-yl)acetic acid, see: Zaderenko et al. (1994 ▶).

Experimental

Crystal data

[Zn(C4H4N3O2)2]

M = 317.57

Monoclinic,

a = 8.791 (1) Å

b = 13.514 (2) Å

c = 10.006 (1) Å

β = 99.458 (1)°

V = 1172.6 (2) Å3

Z = 4

Mo Kα radiation

μ = 2.12 mm−1

T = 293 K

0.38 × 0.20 × 0.11 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ▶) T min = 0.609, T max = 0.792

8509 measured reflections

2286 independent reflections

1956 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.024

wR(F 2) = 0.057

S = 1.04

2286 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.29 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; 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, 1998 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680904001X/lx2113sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680904001X/lx2113Isup2.hkl

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

[Zn(C4H4N3O2)2]	F(000) = 640
Mr = 317.57	Dx = 1.799 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3281 reflections
a = 8.791 (1) Å	θ = 2.6–26.5°
b = 13.514 (2) Å	µ = 2.12 mm−1
c = 10.006 (1) Å	T = 293 K
β = 99.458 (1)°	Block, colorless
V = 1172.6 (2) Å3	0.38 × 0.20 × 0.11 mm
Z = 4

Bruker SMART APEXII CCD diffractometer	2286 independent reflections
Radiation source: fine-focus sealed tube	1956 reflections with I > 2σ(I)
graphite	Rint = 0.022
φ and ω scans	θmax = 26.0°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	h = −10→10
Tmin = 0.609, Tmax = 0.792	k = −16→16
8509 measured reflections	l = −12→12

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)] = 0.024	Hydrogen site location: difference Fourier map
wR(F2) = 0.057	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0228P)2 + 0.7046P] where P = (Fo2 + 2Fc2)/3
2286 reflections	(Δ/σ)max = 0.001
172 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
Zn	0.70429 (3)	0.049976 (17)	0.14839 (2)	0.02917 (9)
O1	1.19552 (19)	0.45868 (11)	0.46359 (16)	0.0407 (4)
O2	1.1138 (2)	0.37002 (13)	0.27788 (17)	0.0499 (5)
O3	0.3598 (2)	−0.34549 (11)	0.49053 (16)	0.0418 (4)
O4	0.4781 (2)	−0.29890 (13)	0.32459 (18)	0.0585 (5)
N1	0.9991 (2)	0.22447 (13)	0.41958 (18)	0.0335 (4)
N2	1.0940 (2)	0.14488 (15)	0.4250 (2)	0.0470 (5)
N3	0.8718 (2)	0.11702 (12)	0.28465 (18)	0.0321 (4)
N4	0.4890 (2)	−0.10956 (12)	0.41086 (17)	0.0306 (4)
N5	0.3571 (2)	−0.06552 (14)	0.3463 (2)	0.0416 (5)
N6	0.5619 (2)	−0.01888 (12)	0.25474 (17)	0.0294 (4)
C1	1.0113 (3)	0.08183 (18)	0.3430 (2)	0.0429 (6)
H1	1.0456	0.0186	0.3266	0.052*
C2	0.8698 (3)	0.20781 (16)	0.3354 (2)	0.0344 (5)
H2	0.7893	0.2528	0.3147	0.041*
C3	1.0519 (3)	0.31596 (17)	0.4896 (2)	0.0401 (6)
H3A	1.1255	0.3003	0.5701	0.048*
H3B	0.9649	0.3492	0.5181	0.048*
C4	1.1271 (2)	0.38505 (16)	0.3997 (2)	0.0333 (5)
C5	0.4076 (3)	−0.01127 (17)	0.2543 (2)	0.0369 (5)
H5	0.3435	0.0289	0.1940	0.044*
C6	0.6078 (3)	−0.08246 (16)	0.3545 (2)	0.0320 (5)
H6	0.7085	−0.1045	0.3805	0.038*
C7	0.4817 (3)	−0.18783 (16)	0.5093 (2)	0.0370 (5)
H7A	0.4055	−0.1714	0.5656	0.044*
H7B	0.5810	−0.1945	0.5674	0.044*
C8	0.4383 (3)	−0.28544 (16)	0.4351 (2)	0.0333 (5)

	U11	U22	U33	U12	U13	U23
Zn	0.03301 (15)	0.02428 (14)	0.02973 (14)	−0.00137 (10)	0.00366 (10)	0.00331 (10)
O1	0.0491 (10)	0.0311 (9)	0.0414 (9)	−0.0133 (7)	0.0059 (8)	−0.0041 (7)
O2	0.0666 (12)	0.0483 (11)	0.0364 (10)	−0.0205 (9)	0.0128 (8)	−0.0035 (8)
O3	0.0579 (11)	0.0291 (8)	0.0379 (9)	−0.0138 (8)	0.0059 (8)	−0.0029 (7)
O4	0.0943 (15)	0.0394 (10)	0.0484 (11)	−0.0108 (10)	0.0309 (11)	−0.0129 (8)
N1	0.0381 (11)	0.0292 (10)	0.0333 (10)	−0.0092 (8)	0.0060 (8)	−0.0011 (8)
N2	0.0451 (13)	0.0363 (11)	0.0531 (13)	0.0013 (9)	−0.0113 (10)	−0.0015 (10)
N3	0.0319 (10)	0.0281 (9)	0.0354 (10)	−0.0043 (7)	0.0032 (8)	−0.0007 (8)
N4	0.0375 (11)	0.0251 (9)	0.0291 (9)	−0.0064 (7)	0.0054 (8)	−0.0006 (7)
N5	0.0344 (11)	0.0418 (12)	0.0494 (12)	−0.0002 (9)	0.0096 (9)	0.0028 (9)
N6	0.0322 (10)	0.0240 (9)	0.0311 (9)	−0.0026 (7)	0.0030 (8)	0.0035 (7)
C1	0.0427 (15)	0.0323 (12)	0.0493 (14)	0.0039 (10)	−0.0059 (11)	−0.0013 (11)
C2	0.0300 (12)	0.0313 (12)	0.0422 (13)	−0.0029 (9)	0.0064 (10)	−0.0008 (10)
C3	0.0503 (15)	0.0370 (13)	0.0336 (12)	−0.0152 (11)	0.0087 (11)	−0.0082 (10)
C4	0.0310 (12)	0.0282 (11)	0.0402 (13)	−0.0029 (9)	0.0044 (10)	0.0000 (9)
C5	0.0328 (13)	0.0354 (12)	0.0414 (13)	0.0032 (10)	0.0027 (10)	0.0053 (10)
C6	0.0306 (12)	0.0299 (11)	0.0347 (12)	−0.0035 (9)	0.0028 (9)	0.0027 (9)
C7	0.0543 (15)	0.0306 (12)	0.0269 (11)	−0.0139 (10)	0.0092 (10)	−0.0012 (9)
C8	0.0421 (13)	0.0273 (11)	0.0288 (11)	−0.0007 (9)	0.0003 (10)	0.0006 (9)

Zn—O1i	1.9693 (15)	N4—C6	1.318 (3)
Zn—O3ii	1.9970 (15)	N4—N5	1.367 (3)
Zn—N6	2.0010 (17)	N4—C7	1.454 (3)
Zn—N3	2.0463 (17)	N5—C5	1.310 (3)
O1—C4	1.278 (3)	N6—C6	1.328 (3)
O1—Zniii	1.9693 (15)	N6—C5	1.359 (3)
O2—C4	1.223 (3)	C1—H1	0.9300
O3—C8	1.252 (3)	C2—H2	0.9300
O3—Zniv	1.9970 (15)	C3—C4	1.520 (3)
O4—C8	1.227 (3)	C3—H3A	0.9700
N1—C2	1.318 (3)	C3—H3B	0.9700
N1—N2	1.357 (3)	C5—H5	0.9300
N1—C3	1.459 (3)	C6—H6	0.9300
N2—C1	1.316 (3)	C7—C8	1.531 (3)
N3—C2	1.329 (3)	C7—H7A	0.9700
N3—C1	1.355 (3)	C7—H7B	0.9700
O1i—Zn—O3ii	98.54 (6)	N1—C2—H2	125.1
O1i—Zn—N6	112.87 (7)	N3—C2—H2	125.1
O3ii—Zn—N6	124.72 (7)	N1—C3—C4	111.80 (18)
O1i—Zn—N3	108.45 (7)	N1—C3—H3A	109.3
O3ii—Zn—N3	103.90 (7)	C4—C3—H3A	109.3
N6—Zn—N3	107.23 (7)	N1—C3—H3B	109.3
C4—O1—Zniii	114.91 (14)	C4—C3—H3B	109.3
C8—O3—Zniv	105.24 (14)	H3A—C3—H3B	107.9
C2—N1—N2	110.52 (18)	O2—C4—O1	126.0 (2)
C2—N1—C3	128.6 (2)	O2—C4—C3	120.6 (2)
N2—N1—C3	120.51 (19)	O1—C4—C3	113.40 (19)
C1—N2—N1	102.41 (18)	N5—C5—N6	114.1 (2)
C2—N3—C1	103.11 (19)	N5—C5—H5	122.9
C2—N3—Zn	127.61 (15)	N6—C5—H5	122.9
C1—N3—Zn	129.27 (15)	N4—C6—N6	109.70 (19)
C6—N4—N5	110.29 (18)	N4—C6—H6	125.2
C6—N4—C7	128.2 (2)	N6—C6—H6	125.2
N5—N4—C7	120.56 (18)	N4—C7—C8	109.48 (17)
C5—N5—N4	102.52 (18)	N4—C7—H7A	109.8
C6—N6—C5	103.36 (18)	C8—C7—H7A	109.8
C6—N6—Zn	124.11 (15)	N4—C7—H7B	109.8
C5—N6—Zn	132.40 (15)	C8—C7—H7B	109.8
N2—C1—N3	114.2 (2)	H7A—C7—H7B	108.2
N2—C1—H1	122.9	O4—C8—O3	124.2 (2)
N3—C1—H1	122.9	O4—C8—C7	118.7 (2)
N1—C2—N3	109.7 (2)	O3—C8—C7	117.06 (19)
C2—N1—N2—C1	−1.5 (3)	C1—N3—C2—N1	−0.7 (2)
C3—N1—N2—C1	−175.3 (2)	Zn—N3—C2—N1	−179.62 (14)
O1i—Zn—N3—C2	148.06 (18)	C2—N1—C3—C4	−82.7 (3)
O3ii—Zn—N3—C2	43.95 (19)	N2—N1—C3—C4	89.9 (2)
N6—Zn—N3—C2	−89.77 (19)	Zniii—O1—C4—O2	−3.3 (3)
O1i—Zn—N3—C1	−30.5 (2)	Zniii—O1—C4—C3	179.67 (15)
O3ii—Zn—N3—C1	−134.6 (2)	N1—C3—C4—O2	13.0 (3)
N6—Zn—N3—C1	91.6 (2)	N1—C3—C4—O1	−169.84 (19)
C6—N4—N5—C5	−1.4 (2)	N4—N5—C5—N6	0.9 (3)
C7—N4—N5—C5	−171.21 (18)	C6—N6—C5—N5	0.0 (3)
O1i—Zn—N6—C6	66.44 (18)	Zn—N6—C5—N5	−175.96 (16)
O3ii—Zn—N6—C6	−174.32 (15)	N5—N4—C6—N6	1.5 (2)
N3—Zn—N6—C6	−52.92 (18)	C7—N4—C6—N6	170.30 (18)
O1i—Zn—N6—C5	−118.3 (2)	C5—N6—C6—N4	−0.9 (2)
O3ii—Zn—N6—C5	0.9 (2)	Zn—N6—C6—N4	175.46 (13)
N3—Zn—N6—C5	122.3 (2)	C6—N4—C7—C8	−88.3 (3)
N1—N2—C1—N3	1.0 (3)	N5—N4—C7—C8	79.5 (2)
C2—N3—C1—N2	−0.2 (3)	Zniv—O3—C8—O4	−7.6 (3)
Zn—N3—C1—N2	178.63 (16)	Zniv—O3—C8—C7	170.28 (16)
N2—N1—C2—N3	1.4 (3)	N4—C7—C8—O4	30.4 (3)
C3—N1—C2—N3	174.63 (19)	N4—C7—C8—O3	−147.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O4ii	0.93	2.62	3.212 (3)	122
C5—H5···O1v	0.93	2.46	3.265 (3)	145
C7—H7A···O4vi	0.97	2.60	3.165 (3)	118

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O4i	0.93	2.62	3.212 (3)	122
C5—H5⋯O1ii	0.93	2.46	3.265 (3)	145
C7—H7A⋯O4iii	0.97	2.60	3.165 (3)	118

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