trans-Diaqua-bis[5-carb-oxy-2-(3-pyrid-yl)-1H-imidazole-4-carboxyl-ato-κN,O]iron(II).

In the title complex, [Fe(C(10)H(6)N(3)O(4))(2)(H(2)O)(2)], the Fe(II) atom is located on an inversion centre and is trans-coordinated by two N,O-bidentate 5-carb-oxy-2-(3-pyrid-yl)-1H-imidazole-4-carb-oxy-l-ate ligands and two water mol-ecules, defining a distorted octa-hedral environment. A two-dimensional network of N-H⋯O and O-H⋯O hydrogen bonds extending parallel to (110) helps to stabilize the crystal packing.

Related literature

N-Heterocyclic carboxylic acids are efficient N/O donors exhibiting versatile coordination modes and hydrogen bonding and can be successively deprotonated, resulting in a large diversity of supra­molecular architectures, see: Gu et al. (2007 ▶); Liu et al. (2004 ▶); Maji et al. (2005 ▶); Rajendiran et al. (2003 ▶); Sun et al. (2005 ▶); Zou et al. (2005 ▶).

Experimental

Crystal data

[Fe(C10H6N3O4)2(H2O)2]

M = 556.24

Triclinic,

a = 7.0100 (14) Å

b = 8.6670 (17) Å

c = 9.4110 (19) Å

α = 82.28 (3)°

β = 83.84 (3)°

γ = 70.66 (3)°

V = 533.41 (18) Å3

Z = 1

Mo Kα radiation

μ = 0.78 mm−1

T = 173 K

0.29 × 0.24 × 0.19 mm

Data collection

Rigaku Mercury CCD diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2000 ▶) T min = 0.826, T max = 0.890

4126 measured reflections

2084 independent reflections

1693 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.105

S = 1.04

2084 reflections

172 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.47 e Å−3

Δρmin = −0.55 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 datablocks I, global. DOI: 10.1107/S1600536809027457/bv2118sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809027457/bv2118Isup2.hkl

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

[Fe(C10H6N3O4)2(H2O)2]	Z = 1
Mr = 556.24	F(000) = 284
Triclinic, P1	Dx = 1.732 Mg m−3
a = 7.0100 (14) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.6670 (17) Å	θ = 2.5–28.0°
c = 9.4110 (19) Å	µ = 0.78 mm−1
α = 82.28 (3)°	T = 173 K
β = 83.84 (3)°	Block, yellow
γ = 70.66 (3)°	0.28 × 0.24 × 0.19 mm
V = 533.41 (18) Å3

Rigaku Mercury CCD diffractometer	2084 independent reflections
Radiation source: fine-focus sealed tube	1693 reflections with I > 2σ(I)
graphite	Rint = 0.023
ω scans	θmax = 26.0°, θmin = 2.5°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2000)	h = −8→8
Tmin = 0.826, Tmax = 0.890	k = −10→10
4126 measured reflections	l = −11→11

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0571P)2 + 0.2007P] where P = (Fo2 + 2Fc2)/3
2084 reflections	(Δ/σ)max < 0.001
172 parameters	Δρmax = 0.47 e Å−3
1 restraint	Δρmin = −0.55 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
Fe1	0.5000	0.5000	0.0000	0.03010 (18)
O1	0.4346 (3)	0.7540 (2)	−0.09416 (18)	0.0407 (5)
O2	0.2752 (3)	1.0178 (2)	−0.06408 (18)	0.0410 (5)
O3	0.0627 (3)	1.1808 (2)	0.12660 (19)	0.0408 (5)
O4	−0.0530 (3)	1.1320 (2)	0.35321 (19)	0.0466 (5)
O5	0.7690 (3)	0.5052 (2)	0.07395 (18)	0.0406 (5)
N1	0.3184 (3)	0.6478 (2)	0.17970 (19)	0.0267 (4)
N2	0.1534 (3)	0.7958 (2)	0.3559 (2)	0.0280 (5)
H2A	0.0841	0.8214	0.4319	0.034*
N3	0.2740 (3)	0.3678 (3)	0.6641 (2)	0.0357 (5)
C1	0.3294 (4)	0.8639 (3)	−0.0195 (2)	0.0313 (6)
C2	0.2649 (3)	0.8126 (3)	0.1308 (2)	0.0258 (5)
C3	0.1588 (4)	0.9068 (3)	0.2385 (2)	0.0277 (5)
C4	0.0479 (4)	1.0858 (3)	0.2420 (3)	0.0322 (6)
C5	0.2483 (3)	0.6410 (3)	0.3177 (2)	0.0259 (5)
C6	0.2686 (4)	0.4921 (3)	0.4180 (2)	0.0269 (5)
C7	0.2554 (4)	0.4991 (3)	0.5672 (2)	0.0313 (6)
H3	0.2321	0.6026	0.6011	0.038*
C8	0.3003 (4)	0.3402 (3)	0.3698 (3)	0.0332 (6)
H4	0.3060	0.3303	0.2700	0.040*
C9	0.3234 (4)	0.2031 (3)	0.4700 (3)	0.0379 (6)
H1	0.3486	0.0977	0.4392	0.045*
C10	0.3092 (4)	0.2212 (3)	0.6157 (3)	0.0360 (6)
H2	0.3250	0.1268	0.6833	0.043*
H5A	0.8761	0.4145	0.0835	0.043*
H5B	0.7552	0.5726	0.1339	0.043*
H3A	0.137 (4)	1.128 (3)	0.057 (2)	0.043*

	U11	U22	U33	U12	U13	U23
Fe1	0.0395 (3)	0.0268 (3)	0.0151 (3)	0.0007 (2)	0.00222 (19)	−0.00396 (19)
O1	0.0548 (12)	0.0334 (10)	0.0192 (8)	0.0012 (9)	0.0110 (8)	−0.0027 (7)
O2	0.0584 (12)	0.0293 (10)	0.0224 (9)	−0.0029 (9)	0.0075 (8)	0.0046 (7)
O3	0.0584 (13)	0.0267 (10)	0.0264 (10)	−0.0017 (9)	0.0053 (8)	−0.0029 (7)
O4	0.0665 (14)	0.0351 (10)	0.0239 (9)	0.0033 (9)	0.0048 (9)	−0.0113 (8)
O5	0.0457 (11)	0.0410 (11)	0.0269 (9)	0.0002 (9)	−0.0032 (8)	−0.0112 (8)
N1	0.0350 (11)	0.0254 (10)	0.0140 (9)	−0.0028 (9)	0.0027 (8)	−0.0035 (8)
N2	0.0352 (11)	0.0279 (11)	0.0152 (9)	−0.0039 (9)	0.0064 (8)	−0.0052 (8)
N3	0.0473 (13)	0.0365 (12)	0.0190 (10)	−0.0098 (10)	0.0000 (9)	0.0003 (9)
C1	0.0391 (14)	0.0307 (13)	0.0164 (11)	−0.0024 (11)	0.0023 (10)	−0.0019 (10)
C2	0.0318 (12)	0.0249 (12)	0.0145 (11)	−0.0025 (10)	0.0024 (9)	−0.0013 (9)
C3	0.0342 (13)	0.0276 (13)	0.0182 (11)	−0.0059 (10)	0.0001 (9)	−0.0030 (9)
C4	0.0385 (14)	0.0304 (13)	0.0225 (12)	−0.0032 (11)	−0.0022 (10)	−0.0054 (10)
C5	0.0304 (12)	0.0266 (12)	0.0165 (11)	−0.0038 (10)	0.0008 (9)	−0.0039 (9)
C6	0.0303 (12)	0.0290 (13)	0.0181 (11)	−0.0064 (10)	0.0021 (9)	−0.0020 (9)
C7	0.0419 (15)	0.0288 (13)	0.0204 (12)	−0.0075 (11)	0.0001 (10)	−0.0046 (10)
C8	0.0447 (15)	0.0312 (14)	0.0198 (11)	−0.0080 (11)	0.0048 (10)	−0.0051 (10)
C9	0.0508 (17)	0.0270 (13)	0.0319 (14)	−0.0079 (12)	0.0008 (12)	−0.0043 (11)
C10	0.0435 (15)	0.0301 (14)	0.0285 (13)	−0.0075 (12)	0.0012 (11)	0.0032 (11)

Fe1—O5i	2.095 (2)	N2—C3	1.369 (3)
Fe1—O5	2.095 (2)	N2—H2A	0.8325
Fe1—O1i	2.1764 (19)	N3—C7	1.338 (3)
Fe1—O1	2.1764 (19)	N3—C10	1.344 (3)
Fe1—N1	2.2719 (19)	C1—C2	1.493 (3)
Fe1—N1i	2.2719 (19)	C2—C3	1.380 (3)
O1—C1	1.244 (3)	C3—C4	1.490 (3)
O2—C1	1.284 (3)	C5—C6	1.469 (3)
O3—C4	1.289 (3)	C6—C8	1.390 (3)
O3—H3A	0.868 (10)	C6—C7	1.405 (3)
O4—C4	1.234 (3)	C7—H3	0.9500
O5—H5A	0.8910	C8—C9	1.390 (3)
O5—H5B	0.8412	C8—H4	0.9500
N1—C5	1.339 (3)	C9—C10	1.390 (4)
N1—C2	1.378 (3)	C9—H1	0.9500
N2—C5	1.364 (3)	C10—H2	0.9500
O5i—Fe1—O5	180.0	O2—C1—C2	118.6 (2)
O5i—Fe1—O1i	90.33 (8)	N1—C2—C3	110.46 (19)
O5—Fe1—O1i	89.67 (8)	N1—C2—C1	119.4 (2)
O5i—Fe1—O1	89.67 (8)	C3—C2—C1	130.1 (2)
O5—Fe1—O1	90.33 (8)	N2—C3—C2	105.0 (2)
O1i—Fe1—O1	180.00 (9)	N2—C3—C4	121.4 (2)
O5i—Fe1—N1	89.91 (7)	C2—C3—C4	133.4 (2)
O5—Fe1—N1	90.09 (7)	O4—C4—O3	124.8 (2)
O1i—Fe1—N1	103.66 (7)	O4—C4—C3	118.2 (2)
O1—Fe1—N1	76.34 (7)	O3—C4—C3	117.0 (2)
O5i—Fe1—N1i	90.09 (7)	N1—C5—N2	110.1 (2)
O5—Fe1—N1i	89.91 (7)	N1—C5—C6	126.8 (2)
O1i—Fe1—N1i	76.34 (7)	N2—C5—C6	123.1 (2)
O1—Fe1—N1i	103.66 (7)	C8—C6—C7	117.7 (2)
N1—Fe1—N1i	180.000 (1)	C8—C6—C5	121.7 (2)
C1—O1—Fe1	117.71 (15)	C7—C6—C5	120.7 (2)
C4—O3—H3A	113 (2)	N3—C7—C6	123.6 (2)
Fe1—O5—H5A	121.1	N3—C7—H3	118.2
Fe1—O5—H5B	115.7	C6—C7—H3	118.2
H5A—O5—H5B	115.2	C9—C8—C6	118.9 (2)
C5—N1—C2	105.66 (18)	C9—C8—H4	120.5
C5—N1—Fe1	145.46 (16)	C6—C8—H4	120.5
C2—N1—Fe1	108.78 (13)	C8—C9—C10	119.5 (2)
C5—N2—C3	108.75 (19)	C8—C9—H1	120.2
C5—N2—H2A	126.9	C10—C9—H1	120.2
C3—N2—H2A	123.4	N3—C10—C9	122.2 (2)
C7—N3—C10	118.1 (2)	N3—C10—H2	118.9
O1—C1—O2	123.7 (2)	C9—C10—H2	118.9
O1—C1—C2	117.7 (2)
O5i—Fe1—O1—C1	87.8 (2)	N1—C2—C3—N2	1.7 (3)
O5—Fe1—O1—C1	−92.2 (2)	C1—C2—C3—N2	−176.4 (3)
O1i—Fe1—O1—C1	−157 (100)	N1—C2—C3—C4	−172.4 (3)
N1—Fe1—O1—C1	−2.2 (2)	C1—C2—C3—C4	9.5 (5)
N1i—Fe1—O1—C1	177.8 (2)	N2—C3—C4—O4	−1.3 (4)
O5i—Fe1—N1—C5	95.8 (3)	C2—C3—C4—O4	172.0 (3)
O5—Fe1—N1—C5	−84.2 (3)	N2—C3—C4—O3	179.7 (2)
O1i—Fe1—N1—C5	5.5 (3)	C2—C3—C4—O3	−7.0 (4)
O1—Fe1—N1—C5	−174.5 (3)	C2—N1—C5—N2	0.0 (3)
N1i—Fe1—N1—C5	−141 (100)	Fe1—N1—C5—N2	175.5 (2)
O5i—Fe1—N1—C2	−88.65 (16)	C2—N1—C5—C6	−179.4 (2)
O5—Fe1—N1—C2	91.35 (16)	Fe1—N1—C5—C6	−3.8 (5)
O1i—Fe1—N1—C2	−178.96 (15)	C3—N2—C5—N1	1.1 (3)
O1—Fe1—N1—C2	1.04 (15)	C3—N2—C5—C6	−179.5 (2)
N1i—Fe1—N1—C2	34 (100)	N1—C5—C6—C8	−23.2 (4)
Fe1—O1—C1—O2	−177.8 (2)	N2—C5—C6—C8	157.6 (2)
Fe1—O1—C1—C2	2.8 (3)	N1—C5—C6—C7	157.2 (2)
C5—N1—C2—C3	−1.0 (3)	N2—C5—C6—C7	−22.1 (4)
Fe1—N1—C2—C3	−178.39 (16)	C10—N3—C7—C6	0.7 (4)
C5—N1—C2—C1	177.3 (2)	C8—C6—C7—N3	0.8 (4)
Fe1—N1—C2—C1	−0.1 (3)	C5—C6—C7—N3	−179.5 (2)
O1—C1—C2—N1	−1.8 (4)	C7—C6—C8—C9	−1.9 (4)
O2—C1—C2—N1	178.8 (2)	C5—C6—C8—C9	178.4 (2)
O1—C1—C2—C3	176.1 (3)	C6—C8—C9—C10	1.6 (4)
O2—C1—C2—C3	−3.3 (4)	C7—N3—C10—C9	−1.1 (4)
C5—N2—C3—C2	−1.7 (3)	C8—C9—C10—N3	−0.1 (4)
C5—N2—C3—C4	173.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O4ii	0.83	2.09	2.852 (3)	152
O5—H5A···O3iii	0.89	2.03	2.899 (3)	165
O5—H5B···N3iv	0.84	2.01	2.780 (3)	152
O3—H3A···O2	0.87 (1)	1.61 (1)	2.479 (3)	176 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O4i	0.83	2.09	2.852 (3)	152
O5—H5A⋯O3ii	0.89	2.03	2.899 (3)	165
O5—H5B⋯N3iii	0.84	2.01	2.780 (3)	152
O3—H3A⋯O2	0.868 (10)	1.613 (11)	2.479 (3)	176 (3)

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