catena-Poly[[(pyrimidine-2-carb-oxy-lic acid)iron(II)]-μ-oxalato].

In the title complex, [Fe(C(2)O(4))(C(5)H(4)N(2)O(4))](n), the Fe(II) ion is coordinated by two oxalate anions and a pyrimidine-2-carb-oxy-lic acid ligand in a slightly distorted octa-hedral geometry. Each oxalate anion chelates to two Fe(II) ions, forming chains along the a axis. The chains are further connected by O-H⋯O and C-H⋯O hydrogen bonds, stabilizing the structure. An intra-molecular O-H⋯N inter-action results in a five-membered ring.

Related literature

For related structures, see: Zhang et al. (2008 ▶).

Experimental

Crystal data

[Fe(C2O4)(C5H4N2O4)]

M = 267.97

Orthorhombic,

a = 9.0524 (18) Å

b = 9.1578 (18) Å

c = 11.329 (2) Å

V = 939.2 (3) Å3

Z = 4

Mo Kα radiation

μ = 1.62 mm−1

T = 293 K

0.20 × 0.18 × 0.16 mm

Data collection

Rigaku SCXmini diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.780, T max = 1

7603 measured reflections

1658 independent reflections

1503 reflections with I > 2σ(I)

R int = 0.074

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.083

S = 1.11

1658 reflections

145 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.46 e Å−3

Δρmin = −0.30 e Å−3

Absolute structure: Flack (1983 ▶), 783 Friedel pairs

Flack parameter: 0.05 (3)

Data collection: SCXmini Benchtop Crystallography System Software (Rigaku, 2006 ▶); cell refinement: PROCESS-AUTO (Rigaku, 1998 ▶); data reduction: PROCESS-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810030023/pv2297sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810030023/pv2297Isup2.hkl

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

[Fe(C2O4)(C5H4N2O4)]	F(000) = 536
Mr = 267.97	Dx = 1.895 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 8691 reflections
a = 9.0524 (18) Å	θ = 3.2–27.5°
b = 9.1578 (18) Å	µ = 1.62 mm−1
c = 11.329 (2) Å	T = 293 K
V = 939.2 (3) Å3	Block, red
Z = 4	0.2 × 0.18 × 0.16 mm

Rigaku SCXmini diffractometer	1658 independent reflections
Radiation source: fine-focus sealed tube	1503 reflections with I > 2σ(I)
graphite	Rint = 0.074
ω scans	θmax = 25.0°, θmin = 3.2°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −10→10
Tmin = 0.780, Tmax = 1	k = −10→10
7603 measured reflections	l = −13→13

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040	H-atom parameters constrained
wR(F2) = 0.083	w = 1/[σ2(Fo2) + (0.0339P)2 + 0.7762P] where P = (Fo2 + 2Fc2)/3
S = 1.11	(Δ/σ)max = 0.001
1658 reflections	Δρmax = 0.46 e Å−3
145 parameters	Δρmin = −0.30 e Å−3
1 restraint	Absolute structure: Flack (1983), 783 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.05 (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 > 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	0.13566 (6)	−0.08170 (6)	0.71653 (7)	0.02969 (18)
C4	0.1749 (5)	0.2409 (5)	0.7015 (4)	0.0263 (10)
O5	0.2520 (4)	0.0586 (3)	0.8376 (3)	0.0397 (9)
O1	−0.0702 (3)	−0.0924 (3)	0.8009 (3)	0.0293 (7)
N1	0.0989 (4)	0.1349 (4)	0.6452 (4)	0.0307 (9)
O6	0.3406 (5)	0.2878 (5)	0.8630 (4)	0.0624 (12)
H6	0.3456	0.3746	0.8369	0.075*
C3	0.2601 (5)	0.1886 (5)	0.8074 (4)	0.0325 (11)
O3	−0.2731 (3)	−0.2329 (4)	0.8046 (3)	0.0353 (8)
O2	0.0098 (4)	−0.2138 (4)	0.5963 (3)	0.0343 (8)
C7	0.0149 (5)	0.1768 (6)	0.5565 (4)	0.0349 (12)
H7A	−0.0405	0.1072	0.5163	0.042*
O4	−0.1781 (4)	−0.3696 (4)	0.6089 (3)	0.0368 (9)
C5	0.0923 (6)	0.4168 (6)	0.5831 (5)	0.0438 (13)
H5A	0.0916	0.5141	0.5597	0.053*
C6	0.0066 (6)	0.3211 (6)	0.5216 (5)	0.0408 (13)
H6A	−0.0539	0.3511	0.4598	0.049*
N2	0.1764 (5)	0.3806 (4)	0.6738 (4)	0.0350 (11)
C2	−0.1034 (5)	−0.2649 (5)	0.6452 (4)	0.0263 (11)
C1	−0.1539 (5)	−0.1906 (5)	0.7602 (4)	0.0256 (10)

	U11	U22	U33	U12	U13	U23
Fe1	0.0248 (3)	0.0246 (3)	0.0396 (4)	−0.0008 (3)	0.0015 (4)	0.0021 (4)
C4	0.028 (2)	0.028 (2)	0.023 (3)	0.0011 (17)	0.002 (2)	−0.002 (2)
O5	0.053 (2)	0.0245 (19)	0.042 (2)	−0.0094 (17)	−0.0203 (18)	0.0093 (15)
O1	0.0252 (17)	0.0282 (17)	0.0344 (19)	0.0003 (15)	0.0030 (15)	−0.0040 (15)
N1	0.030 (2)	0.034 (2)	0.029 (2)	0.0011 (18)	0.0004 (18)	0.0003 (18)
O6	0.076 (3)	0.049 (3)	0.062 (3)	−0.010 (2)	−0.010 (2)	0.007 (2)
C3	0.033 (3)	0.035 (3)	0.029 (3)	−0.007 (2)	−0.006 (2)	−0.001 (2)
O3	0.0304 (19)	0.0338 (19)	0.042 (2)	−0.0084 (16)	0.0102 (17)	−0.0078 (17)
O2	0.0298 (18)	0.0426 (19)	0.0304 (18)	−0.0060 (16)	0.0071 (16)	−0.0054 (17)
C7	0.033 (3)	0.042 (3)	0.030 (3)	−0.002 (2)	−0.007 (2)	−0.003 (2)
O4	0.0292 (18)	0.041 (2)	0.040 (2)	−0.0042 (16)	0.0069 (17)	−0.0142 (17)
C5	0.053 (3)	0.033 (3)	0.045 (3)	0.010 (3)	−0.001 (3)	0.008 (3)
C6	0.043 (3)	0.043 (3)	0.037 (3)	0.010 (3)	−0.008 (3)	0.002 (2)
N2	0.041 (3)	0.024 (2)	0.039 (3)	−0.0041 (17)	−0.0069 (19)	0.0036 (16)
C2	0.023 (2)	0.030 (3)	0.026 (3)	0.007 (2)	−0.001 (2)	−0.001 (2)
C1	0.021 (2)	0.024 (2)	0.032 (2)	0.003 (2)	0.0027 (19)	0.0036 (18)

Fe1—O1	2.097 (3)	O6—H6	0.8500
Fe1—O4i	2.128 (3)	O3—C1	1.252 (5)
Fe1—O3i	2.136 (3)	O3—Fe1ii	2.136 (3)
Fe1—O2	2.148 (3)	O2—C2	1.255 (6)
Fe1—O5	2.154 (3)	C7—C6	1.382 (7)
Fe1—N1	2.168 (4)	C7—H7A	0.9300
C4—N2	1.318 (6)	O4—C2	1.243 (6)
C4—N1	1.350 (6)	O4—Fe1ii	2.128 (3)
C4—C3	1.504 (7)	C5—N2	1.321 (7)
O5—C3	1.240 (6)	C5—C6	1.362 (8)
O1—C1	1.263 (6)	C5—H5A	0.9300
N1—C7	1.317 (6)	C6—H6A	0.9300
O6—C3	1.325 (6)	C2—C1	1.540 (6)
O1—Fe1—O4i	162.87 (14)	C3—O6—H6	120.4
O1—Fe1—O3i	95.38 (13)	O5—C3—O6	124.0 (4)
O4i—Fe1—O3i	78.16 (13)	O5—C3—C4	119.7 (4)
O1—Fe1—O2	77.96 (12)	O6—C3—C4	116.3 (4)
O4i—Fe1—O2	86.49 (14)	C1—O3—Fe1ii	113.1 (3)
O3i—Fe1—O2	93.08 (14)	C2—O2—Fe1	111.3 (3)
O1—Fe1—O5	99.90 (14)	N1—C7—C6	121.9 (5)
O4i—Fe1—O5	95.90 (15)	N1—C7—H7A	119.1
O3i—Fe1—O5	89.29 (13)	C6—C7—H7A	119.1
O2—Fe1—O5	176.94 (13)	C2—O4—Fe1ii	113.7 (3)
O1—Fe1—N1	94.37 (14)	N2—C5—C6	124.4 (5)
O4i—Fe1—N1	95.72 (14)	N2—C5—H5A	117.8
O3i—Fe1—N1	163.96 (15)	C6—C5—H5A	117.8
O2—Fe1—N1	101.40 (14)	C5—C6—C7	115.9 (5)
O5—Fe1—N1	76.50 (14)	C5—C6—H6A	122.0
N2—C4—N1	126.2 (5)	C7—C6—H6A	122.0
N2—C4—C3	119.6 (4)	C4—N2—C5	115.0 (4)
N1—C4—C3	114.2 (4)	O4—C2—O2	125.8 (5)
C3—O5—Fe1	115.2 (3)	O4—C2—C1	117.4 (4)
C1—O1—Fe1	113.6 (3)	O2—C2—C1	116.8 (4)
C7—N1—C4	116.5 (4)	O3—C1—O1	126.2 (4)
C7—N1—Fe1	129.7 (4)	O3—C1—C2	117.3 (4)
C4—N1—Fe1	113.8 (3)	O1—C1—C2	116.5 (4)
O1—Fe1—O5—C3	−99.7 (4)	N1—C4—C3—O5	−2.3 (6)
O4i—Fe1—O5—C3	86.9 (4)	N2—C4—C3—O6	−4.2 (7)
O3i—Fe1—O5—C3	165.0 (4)	N1—C4—C3—O6	177.7 (4)
N1—Fe1—O5—C3	−7.5 (4)	O1—Fe1—O2—C2	−17.7 (3)
O4i—Fe1—O1—C1	−10.5 (6)	O4i—Fe1—O2—C2	155.1 (3)
O3i—Fe1—O1—C1	−77.3 (3)	O3i—Fe1—O2—C2	77.2 (3)
O2—Fe1—O1—C1	14.7 (3)	N1—Fe1—O2—C2	−109.8 (3)
O5—Fe1—O1—C1	−167.5 (3)	C4—N1—C7—C6	1.0 (7)
N1—Fe1—O1—C1	115.5 (3)	Fe1—N1—C7—C6	−178.9 (4)
N2—C4—N1—C7	−2.3 (7)	N2—C5—C6—C7	−2.2 (9)
C3—C4—N1—C7	175.7 (4)	N1—C7—C6—C5	1.0 (8)
N2—C4—N1—Fe1	177.7 (4)	N1—C4—N2—C5	1.2 (7)
C3—C4—N1—Fe1	−4.3 (5)	C3—C4—N2—C5	−176.7 (4)
O1—Fe1—N1—C7	−74.8 (4)	C6—C5—N2—C4	1.2 (8)
O4i—Fe1—N1—C7	91.3 (4)	Fe1ii—O4—C2—O2	−178.8 (4)
O3i—Fe1—N1—C7	157.9 (5)	Fe1ii—O4—C2—C1	1.0 (5)
O2—Fe1—N1—C7	3.8 (4)	Fe1—O2—C2—O4	−162.4 (4)
O5—Fe1—N1—C7	−174.0 (4)	Fe1—O2—C2—C1	17.8 (5)
O1—Fe1—N1—C4	105.3 (3)	Fe1ii—O3—C1—O1	−173.3 (4)
O4i—Fe1—N1—C4	−88.6 (3)	Fe1ii—O3—C1—C2	6.6 (5)
O3i—Fe1—N1—C4	−22.1 (7)	Fe1—O1—C1—O3	169.6 (4)
O2—Fe1—N1—C4	−176.2 (3)	Fe1—O1—C1—C2	−10.3 (5)
O5—Fe1—N1—C4	6.1 (3)	O4—C2—C1—O3	−5.4 (6)
Fe1—O5—C3—O6	−172.2 (4)	O2—C2—C1—O3	174.4 (4)
Fe1—O5—C3—C4	7.8 (6)	O4—C2—C1—O1	174.4 (4)
N2—C4—C3—O5	175.8 (5)	O2—C2—C1—O1	−5.7 (6)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6A···O3iii	0.93	2.48	3.279 (6)	145
O6—H6···O1iv	0.85	2.17	2.988 (5)	161
O6—H6···N2	0.85	2.40	2.743 (6)	105

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6A⋯O3i	0.93	2.48	3.279 (6)	145
O6—H6⋯O1ii	0.85	2.17	2.988 (5)	161
O6—H6⋯N2	0.85	2.40	2.743 (6)	105

Symmetry codes: (i) ; (ii) .