trans-Diaqua-bis[5-carb-oxy-4-carboxyl-ato-2-(4-pyridinio)-1H-imidazol-1-ido-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 a twofold rotation axis and is coordinated by two trans-positioned N,O-bidentate and zwitterionic 5-carboxy-2-(pyridinium-4-yl)-1H-imidazol-1-ide-4-carboxylate H(2)PIDC(-) ligands and two water mol-ecules in a distorted environment. In the crystal packing, a three-dimensional network is constructed via hydrogen-bonding involving the water mol-ecules, uncoordinated imidazole N atom, protonated pyridine N and carboxyl-ate O atoms.

Related literature

For the use of the multifunctional connector 4,5-imidazole­dicarboxylic acid (n class="Chemical">H3IDC) in coordination chemistry, see: Liu et al. (2004 ▶); Maji et al. (2005 ▶); Plieger et al. (2005 ▶); Rajendiran et al. (2003 ▶); Zou et al. (2005 ▶). For the preparation of 2-(pyridin-4-yl)-1H-imidazole-4,5-dicarboxylic acid, see: Sun et al. (2006 ▶).

Experimental

Crystal data

[Fe(C10n class="Species">H6N3O4)2(H2O)2]

M = 556.24

Monoclinic,

a = 21.344 (4) Å

b = 7.3900 (15) Å

c = 13.768 (3) Å

β = 104.70 (3)°

V = 2100.6 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.80 mm−1

T = 173 K

0.25 × 0.15 × 0.12 mm

Data collection

Rigaku Mercury CCD diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2000 ▶) T min = 0.870, T max = 0.921

8952 measured reflections

2386 independent reflections

2083 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.079

S = 1.04

2386 reflections

175 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.37 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 datablocks I, global. DOI: 10.1107/S160053680902337X/kp2221sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680902337X/kp2221Isup2.hkl

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

[Fe(C10H6N3O4)2(H2O)2]	F(000) = 1136
Mr = 556.24	Dx = 1.759 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 21.344 (4) Å	θ = 2.9–28.3°
b = 7.3900 (15) Å	µ = 0.80 mm−1
c = 13.768 (3) Å	T = 173 K
β = 104.70 (3)°	Block, red
V = 2100.6 (7) Å3	0.25 × 0.15 × 0.12 mm
Z = 4

Mercury CCD diffractometer	2386 independent reflections
Radiation source: fine-focus sealed tube	2083 reflections with I > 2σ(I)
graphite	Rint = 0.021
ω scans	θmax = 27.5°, θmin = 2.9°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2000)	h = −27→27
Tmin = 0.870, Tmax = 0.921	k = −9→9
8952 measured reflections	l = −17→17

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.079	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0388P)2 + 2.1264P] where P = (Fo2 + 2Fc2)/3
2386 reflections	(Δ/σ)max < 0.001
175 parameters	Δρmax = 0.37 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
Fe1	0.0000	0.19391 (5)	0.2500	0.02067 (11)
O1	−0.10126 (6)	0.20613 (19)	0.22910 (9)	0.0309 (3)
O2	−0.17764 (6)	0.3056 (2)	0.29923 (10)	0.0391 (4)
O3	−0.18924 (6)	0.3890 (2)	0.46949 (10)	0.0406 (4)
H3B	−0.1867	0.3754	0.3994	0.061*
O4	−0.12932 (7)	0.3875 (2)	0.62503 (10)	0.0452 (4)
O6	0.0000	−0.0877 (3)	0.2500	0.0352 (5)
N1	−0.00912 (6)	0.21688 (19)	0.40741 (10)	0.0203 (3)
N2	−0.01854 (7)	0.2842 (2)	0.56415 (10)	0.0236 (3)
N3	0.21933 (7)	0.1542 (2)	0.63905 (12)	0.0341 (4)
H3	0.2608	0.1397	0.6677	0.051*
C1	0.19580 (9)	0.1005 (3)	0.54346 (14)	0.0334 (4)
H1	0.2237	0.0464	0.5079	0.040*
C2	0.18128 (9)	0.2296 (3)	0.69186 (14)	0.0360 (5)
H2	0.1994	0.2653	0.7595	0.043*
C3	0.11686 (9)	0.2556 (3)	0.64969 (13)	0.0308 (4)
H3A	0.0903	0.3092	0.6877	0.037*
C4	0.13117 (8)	0.1242 (3)	0.49733 (13)	0.0281 (4)
H4	0.1144	0.0871	0.4296	0.034*
C5	0.09009 (8)	0.2030 (2)	0.55010 (12)	0.0220 (3)
C6	0.02077 (8)	0.2333 (2)	0.50603 (12)	0.0210 (3)
C7	−0.07755 (8)	0.3048 (2)	0.49880 (12)	0.0215 (3)
C8	−0.13379 (8)	0.3626 (3)	0.53665 (13)	0.0272 (4)
C9	−0.07183 (7)	0.2631 (2)	0.40239 (12)	0.0205 (3)
C10	−0.11994 (8)	0.2578 (2)	0.30365 (12)	0.0244 (4)
O7	0.0000	0.4810 (3)	0.2500	0.0340 (4)
H6	−0.0101 (12)	−0.153 (3)	0.1969 (18)	0.051*
H7	0.0223 (11)	0.530 (4)	0.2972 (17)	0.051*

	U11	U22	U33	U12	U13	U23
Fe1	0.01809 (17)	0.0276 (2)	0.01644 (17)	0.000	0.00460 (12)	0.000
O1	0.0218 (6)	0.0513 (8)	0.0176 (6)	−0.0004 (6)	0.0017 (5)	−0.0067 (5)
O2	0.0155 (6)	0.0730 (11)	0.0251 (7)	0.0076 (6)	−0.0012 (5)	−0.0053 (6)
O3	0.0198 (6)	0.0712 (10)	0.0312 (7)	0.0084 (6)	0.0071 (5)	−0.0069 (7)
O4	0.0391 (8)	0.0752 (11)	0.0249 (7)	0.0073 (8)	0.0144 (6)	−0.0062 (7)
O6	0.0571 (13)	0.0273 (10)	0.0212 (9)	0.000	0.0096 (9)	0.000
N1	0.0154 (6)	0.0279 (7)	0.0162 (6)	0.0011 (5)	0.0016 (5)	0.0006 (5)
N2	0.0188 (7)	0.0338 (8)	0.0170 (7)	−0.0013 (6)	0.0023 (5)	0.0005 (6)
N3	0.0156 (7)	0.0524 (10)	0.0296 (8)	0.0029 (7)	−0.0026 (6)	0.0055 (7)
C1	0.0236 (9)	0.0457 (11)	0.0315 (10)	0.0055 (8)	0.0079 (7)	0.0021 (8)
C2	0.0238 (9)	0.0558 (13)	0.0231 (9)	−0.0022 (8)	−0.0038 (7)	−0.0021 (8)
C3	0.0217 (9)	0.0473 (11)	0.0215 (9)	−0.0002 (8)	0.0022 (7)	−0.0035 (8)
C4	0.0224 (8)	0.0391 (10)	0.0212 (8)	0.0019 (7)	0.0025 (7)	0.0008 (7)
C5	0.0173 (8)	0.0277 (9)	0.0190 (8)	−0.0009 (6)	0.0013 (6)	0.0039 (6)
C6	0.0179 (8)	0.0274 (8)	0.0161 (7)	−0.0003 (6)	0.0015 (6)	0.0017 (6)
C7	0.0179 (7)	0.0285 (9)	0.0177 (7)	−0.0015 (6)	0.0035 (6)	−0.0004 (6)
C8	0.0230 (8)	0.0360 (10)	0.0235 (8)	−0.0004 (7)	0.0080 (7)	−0.0019 (7)
C9	0.0151 (7)	0.0280 (8)	0.0174 (8)	0.0003 (6)	0.0020 (6)	0.0005 (6)
C10	0.0173 (8)	0.0347 (9)	0.0189 (8)	−0.0013 (7)	0.0004 (6)	−0.0005 (7)
O7	0.0447 (12)	0.0303 (10)	0.0206 (9)	0.000	−0.0033 (8)	0.000

Fe1—O6	2.081 (2)	N3—C2	1.341 (3)
Fe1—O1	2.1087 (13)	N3—C1	1.344 (2)
Fe1—O1i	2.1087 (13)	N3—H3	0.8793
Fe1—O7	2.121 (2)	C1—C4	1.376 (2)
Fe1—N1	2.2311 (14)	C1—H1	0.9500
Fe1—N1i	2.2311 (14)	C2—C3	1.364 (3)
O1—C10	1.251 (2)	C2—H2	0.9500
O2—C10	1.268 (2)	C3—C5	1.400 (2)
O3—C8	1.318 (2)	C3—H3A	0.9500
O3—H3B	0.9857	C4—C5	1.399 (2)
O4—C8	1.210 (2)	C4—H4	0.9500
O6—H6	0.86 (2)	C5—C6	1.467 (2)
N1—C6	1.351 (2)	C7—C9	1.398 (2)
N1—C9	1.366 (2)	C7—C8	1.488 (2)
N2—C6	1.352 (2)	C9—C10	1.482 (2)
N2—C7	1.358 (2)	O7—H7	0.79 (2)
O6—Fe1—O1	92.45 (4)	N3—C2—C3	120.77 (17)
O6—Fe1—O1i	92.45 (4)	N3—C2—H2	119.6
O1—Fe1—O1i	175.09 (8)	C3—C2—H2	119.6
O6—Fe1—O7	180.0	C2—C3—C5	119.65 (18)
O1—Fe1—O7	87.55 (4)	C2—C3—H3A	120.2
O1i—Fe1—O7	87.55 (4)	C5—C3—H3A	120.2
O6—Fe1—N1	94.36 (4)	C1—C4—C5	120.01 (16)
O1—Fe1—N1	77.89 (5)	C1—C4—H4	120.0
O1i—Fe1—N1	101.73 (6)	C5—C4—H4	120.0
O7—Fe1—N1	85.64 (4)	C4—C5—C3	118.05 (15)
O6—Fe1—N1i	94.36 (4)	C4—C5—C6	123.22 (15)
O1—Fe1—N1i	101.73 (6)	C3—C5—C6	118.73 (15)
O1i—Fe1—N1i	77.89 (5)	N1—C6—N2	114.46 (14)
O7—Fe1—N1i	85.64 (4)	N1—C6—C5	124.85 (15)
N1—Fe1—N1i	171.27 (7)	N2—C6—C5	120.68 (14)
C10—O1—Fe1	115.47 (11)	N2—C7—C9	108.34 (14)
C8—O3—H3B	114.1	N2—C7—C8	119.69 (14)
Fe1—O6—H6	124.1 (17)	C9—C7—C8	131.97 (15)
C6—N1—C9	103.60 (13)	O4—C8—O3	120.70 (17)
C6—N1—Fe1	147.96 (11)	O4—C8—C7	122.08 (16)
C9—N1—Fe1	107.20 (10)	O3—C8—C7	117.21 (15)
C6—N2—C7	104.46 (13)	N1—C9—C7	109.12 (14)
C2—N3—C1	121.75 (16)	N1—C9—C10	118.80 (14)
C2—N3—H3	119.1	C7—C9—C10	132.06 (15)
C1—N3—H3	119.2	O1—C10—O2	123.61 (15)
N3—C1—C4	119.76 (17)	O1—C10—C9	118.02 (15)
N3—C1—H1	120.1	O2—C10—C9	118.37 (15)
C4—C1—H1	120.1	Fe1—O7—H7	117.2 (19)
O6—Fe1—O1—C10	108.54 (13)	C7—N2—C6—N1	−0.9 (2)
O1i—Fe1—O1—C10	−71.46 (13)	C7—N2—C6—C5	178.14 (15)
O7—Fe1—O1—C10	−71.46 (13)	C4—C5—C6—N1	−11.1 (3)
N1—Fe1—O1—C10	14.60 (13)	C3—C5—C6—N1	168.70 (17)
N1i—Fe1—O1—C10	−156.48 (13)	C4—C5—C6—N2	169.95 (17)
O6—Fe1—N1—C6	92.7 (2)	C3—C5—C6—N2	−10.3 (3)
O1—Fe1—N1—C6	−175.7 (2)	C6—N2—C7—C9	0.63 (19)
O1i—Fe1—N1—C6	−0.7 (2)	C6—N2—C7—C8	−179.49 (16)
O7—Fe1—N1—C6	−87.3 (2)	N2—C7—C8—O4	−2.2 (3)
N1i—Fe1—N1—C6	−87.3 (2)	C9—C7—C8—O4	177.7 (2)
O6—Fe1—N1—C9	−103.82 (10)	N2—C7—C8—O3	176.82 (16)
O1—Fe1—N1—C9	−12.24 (11)	C9—C7—C8—O3	−3.3 (3)
O1i—Fe1—N1—C9	162.76 (11)	C6—N1—C9—C7	−0.38 (18)
O7—Fe1—N1—C9	76.18 (10)	Fe1—N1—C9—C7	−171.43 (11)
N1i—Fe1—N1—C9	76.18 (10)	C6—N1—C9—C10	−179.12 (15)
C2—N3—C1—C4	0.6 (3)	Fe1—N1—C9—C10	9.83 (18)
C1—N3—C2—C3	−0.4 (3)	N2—C7—C9—N1	−0.2 (2)
N3—C2—C3—C5	0.0 (3)	C8—C7—C9—N1	179.98 (17)
N3—C1—C4—C5	−0.4 (3)	N2—C7—C9—C10	178.35 (17)
C1—C4—C5—C3	0.0 (3)	C8—C7—C9—C10	−1.5 (3)
C1—C4—C5—C6	179.77 (17)	Fe1—O1—C10—O2	166.15 (15)
C2—C3—C5—C4	0.2 (3)	Fe1—O1—C10—C9	−13.9 (2)
C2—C3—C5—C6	−179.60 (18)	N1—C9—C10—O1	1.9 (2)
C9—N1—C6—N2	0.84 (19)	C7—C9—C10—O1	−176.46 (18)
Fe1—N1—C6—N2	164.57 (16)	N1—C9—C10—O2	−178.12 (16)
C9—N1—C6—C5	−178.20 (16)	C7—C9—C10—O2	3.5 (3)
Fe1—N1—C6—C5	−14.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6···N2ii	0.86 (2)	2.04 (2)	2.8806 (18)	169 (3)
N3—H3···O2iii	0.88	1.99	2.707 (2)	138
O3—H3B···O2	0.99	1.53	2.4959 (19)	166

Table 1

Selected bond lengths (Å)

Fe1—O6	2.081 (2)
Fe1—O1	2.1087 (13)
Fe1—O7	2.121 (2)
Fe1—N1	2.2311 (14)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O6—H6⋯N2i	0.86 (2)	2.04 (2)	2.8806 (18)	169 (3)
N3—H3⋯O2ii	0.88	1.99	2.707 (2)	138
O3—H3B⋯O2	0.99	1.53	2.4959 (19)	166

Symmetry codes: (i) ; (ii) .