catena-Poly[iron(II)-bis-{μ-5-carb-oxy-2-[(1H-1,2,4-triazol-1-yl)meth-yl]-1H-imidazole-4-carboxyl-ato}].

In the title coordination polymer, [Fe(C(8)H(6)N(5)O(4))(2)](n) {or [FeL(2)](n),where HL = 2-[(1H-1,2,4-triazol-1-yl) meth-yl]-1H-imidazole-4,5-dicarb-oxy-lic acid)}, the Fe(II) ion, located on an inversion centre, is six-coordinated by two O atoms and four N atoms from two L(-) ligands in a distorted octa-hedral geometry [Fe-O = 2.1452 (13), Fe-N = 2.1316 (14) and 2.2484 (15) Å]. There is an intra-molecular O-H⋯O hydrogen bond in each L(-) ligand. Being an effective tridentate bridging ligand, the deprotonated L(-) anions link two Fe(II) atoms, yielding a chain-like polymer propagating along [100]. In the crystal, these polymer chains are linked via N-H⋯N hydrogen bonds, forming a two-dimensional network.

Related literature

For the design and self-assembly of metal-organic coordination polymers (MOCP’s), see: Batten & Robson (1998 ▶); Eddaoudi et al. (2001 ▶). For related structures, see: Wang et al. (2008 ▶); Meng et al. (2009 ▶); Zhang, Li et al. (2010 ▶); Zhang, Ma et al. (2010 ▶); Feng et al. 2010 ▶); Li et al. (2010 ▶); Chen et al. (2010 ▶); Jing et al. (2010 ▶).

Experimental

Crystal data

[Fe(C8H6N5O4)2]

M = 528.21

Monoclinic,

a = 7.1790 (14) Å

b = 13.490 (3) Å

c = 10.129 (2) Å

β = 99.11 (3)°

V = 968.6 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.85 mm−1

T = 293 K

0.30 × 0.15 × 0.10 mm

Data collection

Rigaku Mercury CCD diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2000 ▶) T min = 0.784, T max = 0.919

10179 measured reflections

1900 independent reflections

1847 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.073

S = 1.08

1900 reflections

160 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.25 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/S1600536811036026/su2292sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811036026/su2292Isup2.hkl

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

[Fe(C8H6N5O4)2]	F(000) = 536
Mr = 528.21	Dx = 1.811 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3321 reflections
a = 7.1790 (14) Å	θ = 2.0–31.1°
b = 13.490 (3) Å	µ = 0.85 mm−1
c = 10.129 (2) Å	T = 293 K
β = 99.11 (3)°	Prism, yellow
V = 968.6 (3) Å3	0.30 × 0.15 × 0.10 mm
Z = 2

Rigaku Mercury CCD diffractometer	1900 independent reflections
Radiation source: fine-focus sealed tube	1847 reflections with I > 2σ(I)
graphite	Rint = 0.020
ω scans	θmax = 26.0°, θmin = 2.5°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2000)	h = −8→8
Tmin = 0.784, Tmax = 0.919	k = −16→16
10179 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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.073	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0398P)2 + 0.4416P] where P = (Fo2 + 2Fc2)/3
1900 reflections	(Δ/σ)max < 0.001
160 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.25 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

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
Fe1	0.00000	0.00000	0.00000	0.0218 (1)
O1	0.06876 (16)	0.10364 (9)	−0.14553 (12)	0.0289 (3)
O2	−0.00859 (18)	0.15001 (9)	−0.35930 (13)	0.0354 (4)
O3	−0.19925 (18)	0.08021 (10)	−0.56865 (12)	0.0349 (4)
O4	−0.38127 (18)	−0.05047 (10)	−0.62554 (12)	0.0351 (4)
N1	−0.51150 (18)	−0.17230 (10)	−0.08531 (13)	0.0226 (4)
N2	−0.5674 (2)	−0.23038 (11)	0.01037 (16)	0.0345 (5)
N3	−0.75834 (19)	−0.09910 (10)	−0.02990 (14)	0.0261 (4)
N4	−0.16330 (18)	−0.05447 (9)	−0.17946 (13)	0.0217 (4)
N5	−0.32936 (18)	−0.11788 (10)	−0.36005 (13)	0.0235 (4)
C1	−0.7157 (3)	−0.18384 (14)	0.0396 (2)	0.0361 (6)
C2	−0.6267 (2)	−0.09475 (12)	−0.10846 (16)	0.0248 (5)
C3	−0.3469 (2)	−0.20523 (12)	−0.14359 (18)	0.0272 (5)
C4	−0.2792 (2)	−0.12666 (11)	−0.22693 (16)	0.0216 (4)
C5	−0.1404 (2)	0.00355 (11)	−0.28705 (16)	0.0217 (5)
C6	−0.0165 (2)	0.09232 (12)	−0.26313 (16)	0.0245 (4)
C7	−0.2437 (2)	−0.03540 (12)	−0.40038 (16)	0.0228 (5)
C8	−0.2797 (2)	−0.00276 (12)	−0.54165 (17)	0.0259 (5)
H1A	−0.78580	−0.20710	0.10290	0.0430*
H2A	−0.61660	−0.04490	−0.17040	0.0300*
H3A	−0.13760	0.10250	−0.50000	0.0520*
H3B	−0.38060	−0.26360	−0.19810	0.0330*
H3C	−0.24600	−0.22340	−0.07230	0.0330*
H5A	−0.40260	−0.15730	−0.41090	0.0280*

	U11	U22	U33	U12	U13	U23
Fe1	0.0216 (2)	0.0231 (2)	0.0203 (2)	0.0023 (1)	0.0022 (1)	−0.0003 (1)
O1	0.0284 (6)	0.0284 (6)	0.0293 (6)	−0.0064 (5)	0.0031 (5)	−0.0015 (5)
O2	0.0361 (7)	0.0321 (7)	0.0375 (7)	−0.0095 (5)	0.0041 (5)	0.0108 (5)
O3	0.0412 (7)	0.0376 (7)	0.0263 (6)	−0.0011 (6)	0.0069 (5)	0.0070 (5)
O4	0.0399 (7)	0.0399 (7)	0.0240 (6)	0.0047 (6)	0.0009 (5)	−0.0041 (5)
N1	0.0236 (7)	0.0206 (7)	0.0247 (7)	0.0014 (5)	0.0070 (5)	0.0047 (5)
N2	0.0359 (8)	0.0312 (8)	0.0406 (9)	0.0099 (7)	0.0191 (7)	0.0174 (7)
N3	0.0258 (7)	0.0249 (7)	0.0282 (7)	0.0049 (5)	0.0061 (6)	0.0023 (6)
N4	0.0217 (6)	0.0217 (7)	0.0224 (6)	−0.0002 (5)	0.0053 (5)	0.0006 (5)
N5	0.0236 (7)	0.0229 (7)	0.0241 (7)	−0.0025 (5)	0.0045 (5)	−0.0039 (5)
C1	0.0365 (10)	0.0333 (10)	0.0435 (11)	0.0095 (8)	0.0214 (8)	0.0130 (8)
C2	0.0284 (8)	0.0225 (8)	0.0238 (8)	0.0040 (6)	0.0051 (6)	0.0035 (6)
C3	0.0268 (8)	0.0215 (8)	0.0360 (9)	0.0023 (6)	0.0132 (7)	0.0023 (7)
C4	0.0204 (7)	0.0205 (7)	0.0250 (8)	0.0016 (6)	0.0073 (6)	−0.0006 (6)
C5	0.0207 (8)	0.0229 (8)	0.0224 (8)	0.0007 (6)	0.0062 (6)	0.0021 (6)
C6	0.0210 (7)	0.0248 (8)	0.0289 (8)	0.0003 (6)	0.0073 (6)	0.0010 (6)
C7	0.0214 (8)	0.0248 (8)	0.0232 (8)	0.0014 (6)	0.0069 (6)	−0.0002 (6)
C8	0.0243 (8)	0.0310 (9)	0.0236 (8)	0.0079 (6)	0.0077 (7)	0.0015 (6)

Fe1—O1	2.1452 (13)	N3—C2	1.330 (2)
Fe1—N4	2.1316 (14)	N3—C1	1.352 (2)
Fe1—N3i	2.2484 (15)	N4—C4	1.321 (2)
Fe1—N3ii	2.2484 (15)	N4—C5	1.373 (2)
Fe1—O1iii	2.1452 (13)	N5—C7	1.365 (2)
Fe1—N4iii	2.1316 (14)	N5—C4	1.345 (2)
O1—C6	1.259 (2)	N5—H5A	0.8600
O2—C6	1.255 (2)	C3—C4	1.484 (2)
O3—C8	1.308 (2)	C5—C6	1.489 (2)
O4—C8	1.213 (2)	C5—C7	1.369 (2)
O3—H3A	0.8200	C7—C8	1.480 (2)
N1—C2	1.331 (2)	C1—H1A	0.9300
N1—C3	1.471 (2)	C2—H2A	0.9300
N1—N2	1.356 (2)	C3—H3B	0.9700
N2—C1	1.310 (3)	C3—H3C	0.9700
O1—Fe1—N4	78.11 (6)	C7—N5—H5A	126.00
O1—Fe1—N3i	91.64 (6)	N2—C1—N3	114.38 (18)
O1—Fe1—N3ii	88.36 (6)	N1—C2—N3	109.91 (14)
O1—Fe1—O1iii	180.00	N1—C3—C4	111.65 (13)
O1—Fe1—N4iii	101.89 (6)	N5—C4—C3	125.00 (14)
N3i—Fe1—N4	90.69 (6)	N4—C4—N5	110.69 (14)
N3ii—Fe1—N4	89.31 (6)	N4—C4—C3	124.31 (15)
O1iii—Fe1—N4	101.89 (6)	N4—C5—C7	109.26 (14)
N4—Fe1—N4iii	180.00	N4—C5—C6	118.24 (14)
N3i—Fe1—N3ii	180.00	C6—C5—C7	132.51 (15)
O1iii—Fe1—N3i	88.36 (6)	O1—C6—O2	125.73 (15)
N3i—Fe1—N4iii	89.31 (6)	O1—C6—C5	116.10 (14)
O1iii—Fe1—N3ii	91.64 (6)	O2—C6—C5	118.15 (15)
N3ii—Fe1—N4iii	90.69 (6)	C5—C7—C8	133.23 (15)
O1iii—Fe1—N4iii	78.11 (6)	N5—C7—C5	105.78 (14)
Fe1—O1—C6	116.15 (11)	N5—C7—C8	120.92 (14)
C8—O3—H3A	109.00	O3—C8—O4	122.94 (16)
N2—N1—C3	117.39 (13)	O3—C8—C7	116.19 (14)
C2—N1—C3	133.07 (14)	O4—C8—C7	120.86 (15)
N2—N1—C2	109.52 (13)	N2—C1—H1A	123.00
N1—N2—C1	103.17 (15)	N3—C1—H1A	123.00
Fe1iv—N3—C1	123.27 (13)	N1—C2—H2A	125.00
Fe1iv—N3—C2	133.72 (11)	N3—C2—H2A	125.00
C1—N3—C2	103.01 (15)	N1—C3—H3B	109.00
Fe1—N4—C5	111.20 (10)	N1—C3—H3C	109.00
C4—N4—C5	106.21 (13)	C4—C3—H3B	109.00
Fe1—N4—C4	142.58 (11)	C4—C3—H3C	109.00
C4—N5—C7	108.07 (13)	H3B—C3—H3C	108.00
C4—N5—H5A	126.00
N4—Fe1—O1—C6	3.33 (11)	Fe1—N4—C4—C3	3.5 (3)
N3i—Fe1—O1—C6	93.69 (12)	C5—N4—C4—N5	0.72 (17)
N3ii—Fe1—O1—C6	−86.31 (12)	C5—N4—C4—C3	−178.19 (14)
N4iii—Fe1—O1—C6	−176.67 (11)	Fe1—N4—C5—C6	−1.63 (17)
O1—Fe1—N4—C4	177.56 (18)	Fe1—N4—C5—C7	178.49 (10)
O1—Fe1—N4—C5	−0.67 (10)	C4—N4—C5—C6	179.49 (13)
N3i—Fe1—N4—C4	86.04 (18)	C4—N4—C5—C7	−0.39 (17)
N3i—Fe1—N4—C5	−92.20 (11)	C7—N5—C4—N4	−0.78 (18)
N3ii—Fe1—N4—C4	−93.96 (18)	C7—N5—C4—C3	178.12 (14)
N3ii—Fe1—N4—C5	87.80 (11)	C4—N5—C7—C5	0.50 (17)
O1iii—Fe1—N4—C4	−2.44 (18)	C4—N5—C7—C8	−176.74 (14)
O1iii—Fe1—N4—C5	179.33 (10)	N1—C3—C4—N4	84.25 (18)
Fe1—O1—C6—O2	173.29 (13)	N1—C3—C4—N5	−94.50 (18)
Fe1—O1—C6—C5	−5.11 (17)	N4—C5—C6—O1	4.6 (2)
C2—N1—N2—C1	0.14 (19)	N4—C5—C6—O2	−173.91 (14)
C3—N1—N2—C1	−178.66 (15)	C7—C5—C6—O1	−175.54 (16)
N2—N1—C2—N3	0.34 (18)	C7—C5—C6—O2	5.9 (3)
C3—N1—C2—N3	178.87 (16)	N4—C5—C7—N5	−0.07 (17)
N2—N1—C3—C4	−169.17 (14)	N4—C5—C7—C8	176.68 (16)
C2—N1—C3—C4	12.4 (2)	C6—C5—C7—N5	−179.92 (15)
N1—N2—C1—N3	−0.6 (2)	C6—C5—C7—C8	−3.2 (3)
C2—N3—C1—N2	0.8 (2)	N5—C7—C8—O3	176.25 (14)
Fe1iv—N3—C1—N2	−178.52 (12)	N5—C7—C8—O4	−2.5 (2)
C1—N3—C2—N1	−0.64 (18)	C5—C7—C8—O3	−0.1 (3)
Fe1iv—N3—C2—N1	178.54 (11)	C5—C7—C8—O4	−178.83 (17)
Fe1—N4—C4—N5	−177.57 (13)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O2	0.82	1.70	2.5175 (19)	179
N5—H5A···N2v	0.86	2.01	2.850 (2)	166

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯O2	0.82	1.70	2.5175 (19)	179
N5—H5A⋯N2i	0.86	2.01	2.850 (2)	166

Symmetry code: (i) .