Diaqua-bis-(5-carb-oxy-1H-imidazole-4-carboxyl-ato-κN,O)iron(II).

In the title compound, [Fe(C(5)H(3)N(2)O(4))(2)(H(2)O)(2)], the Fe(II) ion lies on an inversion centre and is coordinated by two N and two O atoms from two 5-carb-oxy-1H-imidazole-4-carboxyl-ate ligands and two water mol-ecules in a distorted octa-hedral geometry. An intra-molecular O-H⋯O hydrogen bond occurs. In the crystal, inter-molecular N-H⋯O and O-H⋯O hydrogen bonds form a three-dimensional network, which consolidates the packing.

Related literature

For the diversity of coordination architectures of the metal atom in complexes with 4,5-dicarb­oxy­imidazole, see: Shimizu et al. (2004 ▶); Fang & Zhang (2006 ▶). For the closely related crystal structures of the Zn, Mg and Cd complexes, see: Ma et al. (2003 ▶), Liu et al. (2004 ▶) and Zhang et al. (2004 ▶), respectively.

Experimental

Crystal data

[Fe(C5H3N2O4)2(H2O)2]

M = 402.07

Monoclinic,

a = 5.0676 (9) Å

b = 22.769 (4) Å

c = 6.6725 (9) Å

β = 113.733 (10)°

V = 704.8 (2) Å3

Z = 2

Mo Kα radiation

μ = 1.14 mm−1

T = 298 K

0.32 × 0.28 × 0.25 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.712, T max = 0.764

2872 measured reflections

1240 independent reflections

976 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.080

S = 1.05

1240 reflections

116 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811024779/cv5111sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811024779/cv5111Isup2.hkl

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

[Fe(C5H3N2O4)2(H2O)2]	F(000) = 408
Mr = 402.07	Dx = 1.895 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1102 reflections
a = 5.0676 (9) Å	θ = 3.5–23.7°
b = 22.769 (4) Å	µ = 1.14 mm−1
c = 6.6725 (9) Å	T = 298 K
β = 113.733 (10)°	Block, pale-yellow
V = 704.8 (2) Å3	0.32 × 0.28 × 0.25 mm
Z = 2

Bruker SMART APEXII CCD area-detector diffractometer	1240 independent reflections
Radiation source: fine-focus sealed tube	976 reflections with I > 2σ(I)
graphite	Rint = 0.027
φ and ω scans	θmax = 25.2°, θmin = 3.5°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −6→5
Tmin = 0.712, Tmax = 0.764	k = −26→26
2872 measured reflections	l = −4→7

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.080	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0375P)2 + 0.0621P] where P = (Fo2 + 2Fc2)/3
1240 reflections	(Δ/σ)max < 0.001
116 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.25 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	1.2587 (6)	0.86826 (13)	0.4808 (4)	0.0322 (7)
H1	1.4476	0.8718	0.5837	0.039*
C2	0.8201 (6)	0.88774 (11)	0.2661 (4)	0.0265 (6)
C3	0.8639 (6)	0.82984 (12)	0.2373 (4)	0.0279 (6)
C4	0.5611 (5)	0.92523 (12)	0.1742 (4)	0.0268 (6)
C5	0.6789 (7)	0.78182 (14)	0.1066 (5)	0.0369 (7)
Fe1	1.0000	1.0000	0.5000	0.0278 (2)
N1	1.0693 (5)	0.91158 (10)	0.4203 (3)	0.0289 (6)
N2	1.1435 (5)	0.81868 (10)	0.3749 (4)	0.0335 (6)
H2	1.2302	0.7855	0.3906	0.040*
O1	0.5823 (4)	0.97682 (8)	0.2452 (3)	0.0313 (5)
O2	0.3337 (4)	0.90334 (9)	0.0295 (3)	0.0370 (5)
O3	0.4133 (4)	0.79590 (9)	−0.0221 (3)	0.0462 (6)
H3	0.3975	0.8318	−0.0301	0.069*
O4	0.7646 (5)	0.73195 (9)	0.1211 (4)	0.0515 (6)
O1W	0.8685 (4)	0.96305 (9)	0.7355 (3)	0.0392 (5)
H1W	1.0038	0.9508	0.8520	0.059*
H2W	0.7663	0.9851	0.7785	0.059*

	U11	U22	U33	U12	U13	U23
C1	0.0267 (15)	0.0259 (17)	0.0363 (16)	0.0013 (13)	0.0045 (12)	−0.0015 (13)
C2	0.0257 (15)	0.0223 (16)	0.0300 (14)	−0.0002 (12)	0.0098 (12)	0.0011 (12)
C3	0.0274 (16)	0.0224 (16)	0.0320 (15)	0.0013 (13)	0.0101 (12)	0.0011 (12)
C4	0.0259 (16)	0.0258 (18)	0.0268 (14)	0.0010 (12)	0.0088 (12)	0.0022 (12)
C5	0.0379 (18)	0.0283 (18)	0.0430 (18)	−0.0011 (15)	0.0144 (14)	−0.0057 (14)
Fe1	0.0267 (3)	0.0203 (3)	0.0314 (3)	0.0024 (3)	0.0067 (2)	−0.0026 (2)
N1	0.0271 (13)	0.0217 (13)	0.0331 (12)	0.0008 (11)	0.0073 (10)	−0.0030 (10)
N2	0.0316 (14)	0.0218 (14)	0.0432 (14)	0.0079 (11)	0.0110 (11)	0.0020 (11)
O1	0.0282 (11)	0.0220 (11)	0.0375 (11)	0.0047 (9)	0.0068 (9)	−0.0019 (9)
O2	0.0277 (11)	0.0317 (12)	0.0402 (11)	0.0007 (10)	0.0018 (9)	0.0000 (9)
O3	0.0367 (12)	0.0286 (13)	0.0570 (14)	−0.0070 (10)	0.0019 (10)	−0.0073 (11)
O4	0.0512 (15)	0.0258 (13)	0.0703 (16)	−0.0008 (11)	0.0169 (12)	−0.0131 (11)
O1W	0.0346 (12)	0.0437 (14)	0.0385 (11)	0.0168 (10)	0.0140 (9)	0.0092 (10)

C1—N1	1.321 (3)	C5—O3	1.312 (3)
C1—N2	1.335 (3)	Fe1—O1Wi	2.1128 (19)
C1—H1	0.9300	Fe1—O1W	2.1128 (19)
C2—C3	1.363 (4)	Fe1—N1	2.147 (2)
C2—N1	1.379 (3)	Fe1—N1i	2.147 (2)
C2—C4	1.476 (4)	Fe1—O1	2.1801 (18)
C3—N2	1.367 (3)	Fe1—O1i	2.1801 (18)
C3—C5	1.475 (4)	N2—H2	0.8600
C4—O1	1.255 (3)	O3—H3	0.8200
C4—O2	1.270 (3)	O1W—H1W	0.8498
C5—O4	1.206 (3)	O1W—H2W	0.8499
N1—C1—N2	111.1 (2)	O1Wi—Fe1—O1	90.82 (7)
N1—C1—H1	124.4	O1W—Fe1—O1	89.18 (7)
N2—C1—H1	124.4	N1—Fe1—O1	77.53 (8)
C3—C2—N1	109.5 (2)	N1i—Fe1—O1	102.47 (8)
C3—C2—C4	132.0 (2)	O1Wi—Fe1—O1i	89.18 (7)
N1—C2—C4	118.4 (2)	O1W—Fe1—O1i	90.82 (7)
C2—C3—N2	105.6 (2)	N1—Fe1—O1i	102.47 (8)
C2—C3—C5	134.4 (2)	N1i—Fe1—O1i	77.53 (7)
N2—C3—C5	120.0 (2)	O1—Fe1—O1i	179.999 (1)
O1—C4—O2	124.6 (2)	C1—N1—C2	105.6 (2)
O1—C4—C2	117.2 (2)	C1—N1—Fe1	142.71 (18)
O2—C4—C2	118.2 (2)	C2—N1—Fe1	111.22 (17)
O4—C5—O3	121.6 (3)	C1—N2—C3	108.2 (2)
O4—C5—C3	121.9 (3)	C1—N2—H2	125.9
O3—C5—C3	116.5 (3)	C3—N2—H2	125.9
O1Wi—Fe1—O1W	179.998 (1)	C4—O1—Fe1	115.45 (16)
O1Wi—Fe1—N1	93.27 (8)	C5—O3—H3	109.5
O1W—Fe1—N1	86.73 (8)	Fe1—O1W—H1W	115.5
O1Wi—Fe1—N1i	86.73 (8)	Fe1—O1W—H2W	115.7
O1W—Fe1—N1i	93.27 (8)	H1W—O1W—H2W	105.2
N1—Fe1—N1i	179.999 (1)
N1—C2—C3—N2	−0.4 (3)	O1Wi—Fe1—N1—C1	96.8 (3)
C4—C2—C3—N2	−176.4 (3)	O1W—Fe1—N1—C1	−83.2 (3)
N1—C2—C3—C5	176.3 (3)	O1—Fe1—N1—C1	−173.1 (3)
C4—C2—C3—C5	0.3 (5)	O1i—Fe1—N1—C1	6.9 (3)
C3—C2—C4—O1	174.6 (3)	O1Wi—Fe1—N1—C2	−93.03 (18)
N1—C2—C4—O1	−1.1 (4)	O1W—Fe1—N1—C2	86.97 (18)
C3—C2—C4—O2	−5.5 (4)	O1—Fe1—N1—C2	−2.91 (16)
N1—C2—C4—O2	178.8 (2)	O1i—Fe1—N1—C2	177.09 (16)
C2—C3—C5—O4	−174.3 (3)	N1—C1—N2—C3	0.1 (3)
N2—C3—C5—O4	1.9 (5)	C2—C3—N2—C1	0.2 (3)
C2—C3—C5—O3	3.9 (5)	C5—C3—N2—C1	−177.1 (3)
N2—C3—C5—O3	−179.8 (3)	O2—C4—O1—Fe1	178.5 (2)
N2—C1—N1—C2	−0.3 (3)	C2—C4—O1—Fe1	−1.6 (3)
N2—C1—N1—Fe1	170.2 (2)	O1Wi—Fe1—O1—C4	95.72 (19)
C3—C2—N1—C1	0.4 (3)	O1W—Fe1—O1—C4	−84.28 (19)
C4—C2—N1—C1	177.0 (2)	N1—Fe1—O1—C4	2.55 (18)
C3—C2—N1—Fe1	−173.45 (18)	N1i—Fe1—O1—C4	−177.45 (18)
C4—C2—N1—Fe1	3.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O3ii	0.86	2.05	2.897 (3)	169
O3—H3···O2	0.82	1.74	2.525 (3)	160
O1W—H1W···O2iii	0.85	1.94	2.744 (3)	157
O1W—H2W···O1iv	0.85	1.92	2.710 (3)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O3i	0.86	2.05	2.897 (3)	169
O3—H3⋯O2	0.82	1.74	2.525 (3)	160
O1W—H1W⋯O2ii	0.85	1.94	2.744 (3)	157
O1W—H2W⋯O1iii	0.85	1.92	2.710 (3)	155

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