trans-Diaqua­bis[5-carb­oxy-2-(3-pyrid­yl)-1H-imidazole-4-carboxyl­ato-κ2N3,O4]iron(II)

Liu, W.; Zhang, G.; Li, X.; Wu, B.-L.; Zhang, H.-Y.

doi:10.1107/S1600536809027457

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Pages m938-m939

doi:10.1107/S1600536809027457

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trans-Diaquabis[5-carboxy-2-(3-pyridyl)-1H-imidazole-4-carboxylato-κ²N³,O⁴]iron(II)

Wei Liu,^a Gang Zhang,^a Xia Li,^a ^* Ben-Lai Wu ^b ^* and Hong-Yun Zhang ^b

^aDepartment of Chemistry and Chemical Engineering, Henan University of Urban Construction, Pingdingshan, Henan 467044, People's Republic of China, and ^bDepartment of Chemistry, Zhengzhou University, Zhengzhou, Henan 450052, People's Republic of China
^*Correspondence e-mail: lixia@zzu.edu.cn, wbl@zzu.edu.cn

(Received 10 March 2009; accepted 13 July 2009; online 18 July 2009)

In the title complex, [Fe(C₁₀H₆N₃O₄)₂(H₂O)₂], the Fe^II atom is located on an inversion centre and is trans-coordinated by two N,O-bidentate 5-carboxy-2-(3-pyridyl)-1H-imidazole-4-carboxylate ligands and two water molecules, defining a distorted octahedral 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_r = 556.24
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.038
wR(F²) = 0.105
S = 1.04
2084 reflections
172 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.55 e Å⁻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) -x, -y+2, -z+1; (ii) x+1, y-1, z; (iii) -x+1, -y+1, -z+1.

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809027457/bv2118sup1.cif

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

checkCIF report

Comment top

N-Heterocyclic carboxylic acids, such as imidazole-4,5-dicarboxylic acid (H₃IDC), are recognized as efficient N/O donors exhibiting versatile coordination modes and hydrogen bonding. It can be successively deprotonated to generate various species with different proton numbers (H₂IDC^-, HIDC^2-, and IDC^3-), and hence may result in a large diversity of supramolecular architectures (Sun et al., 2005; Maji et al., 2005; Liu et al., 2004; Zou et al., 2005; Rajendiran et al., 2003; Gu et al., 2007). In contrast to the well studied H₃IDC, 2-(pyridin-4-yl)-1H-imidazole-4,5-dicarboxylate acid (H₃PIDC), a very close analogue of H₃IDC, still remains unexplored till now. We report here the single-crystal structure of a new compound, [Fe(H₂PIDC)₂(H₂O)₂] (I), in which the H₂PIDC monoanion coordinates to the Fe atom, acting as a bidentate ligand.

As shown in Fig. 1, the molecule of (I) is a discrete neutral monomer, in which the Fe atom resides on a crystallographic inversion centre and the asymmetric unit contains one-half of the [Fe(H₂PIDC)₂(H₂O)₂] formula unit. Each Fe atom is six-coordinated by two N and two O atoms from two H₂PIDC ligands and two water molecule in a highly distorted octahedral geometry. In this complex, the carboxylic acid (H₃PIDC) ligand is singly deprotonated and bears a formal charge of -1, and the uncoordinated carboxylate atoms O3 and O2 form an intramolecular hydrogen bond (Table 1). All non-H atoms in the imidazole-4,5-dicarboxyl group are nearly coplanar [the mean deviation is 0.031 (9) Å], and the dihedral angle between imidazole group and pyridine group is 22.6 (1) °. At list in Table 2, a two-dimensional supramolecular layer is constructed via hydrogen-bonding interactions involving the coordinated water molecules, the carboxy O atoms and the protonated imidazole N atoms (Fig.2), and these two-dimensional layers are parallel arranged along b axis (Fig. 3).

Related literature top

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 top

A mixture of Fe(II) sulfate (0.056 g, 0.2 mmol), 2-(pyridin-3-yl)-1H-imidazole-4,5-dicarboxylic acid (0.047 g, 0.2 mmol) and water (10 ml) was sealed into a Teflon-lined stainless autoclave and heated at 433 K for 4 days. The bomb was allowed to cooled to room temperature gradually and red prismatic crystals of (I) were obtained. Analysis calculated for C₂₀H₁₆FeN₆O₁₀: C 43.19, H 2.90, N 15.11; found: C 43.12, H 2.94, N 15.13.

Computing details top

Data collection: CrystalClear (Rigaku, 2000); cell refinement: CrystalClear (Rigaku, 2000); data reduction: CrystalClear (Rigaku, 2000); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. A view of the molecular of (I), showing the atom-labelling scheme and displacement ellipsoids at the 30% probability level.
	Fig. 2. The crystal packing of (I), showing the two-dimensional hydrogen-bonding network, H atoms not involved in hydrogen bonding have been omited.
	Fig. 3. Packing diagram of two-dimensional layers along the b axis.

trans-Diaquabis[5-carboxy-2-(3-pyridyl)-1H-imidazole-4- carboxylato-κ²N³,O⁴]iron(II) top

Crystal data top

[Fe(C₁₀H₆N₃O₄)₂(H₂O)₂]	Z = 1
M_r = 556.24	F(000) = 284
Triclinic, P1	D_x = 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)°	0.29 × 0.24 × 0.19 mm
V = 533.41 (18) Å³

Data collection top

Rigaku Mercury CCD diffractometer	2084 independent reflections
Radiation source: fine-focus sealed tube	1693 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
ω scans	θ_max = 26.0°, θ_min = 2.5°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2000)	h = −8→8
T_min = 0.826, T_max = 0.890	k = −10→10
4126 measured reflections	l = −11→11

Refinement top

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(F_o²) + (0.0571P)² + 0.2007P] where P = (F_o² + 2F_c²)/3
2084 reflections	(Δ/σ)_max < 0.001
172 parameters	Δρ_max = 0.47 e Å⁻³
1 restraint	Δρ_min = −0.55 e Å⁻³

Crystal data top

[Fe(C₁₀H₆N₃O₄)₂(H₂O)₂]	γ = 70.66 (3)°
M_r = 556.24	V = 533.41 (18) Å³
Triclinic, P1	Z = 1
a = 7.0100 (14) Å	Mo Kα radiation
b = 8.6670 (17) Å	µ = 0.78 mm⁻¹
c = 9.4110 (19) Å	T = 173 K
α = 82.28 (3)°	0.29 × 0.24 × 0.19 mm
β = 83.84 (3)°

Data collection top

Rigaku Mercury CCD diffractometer	2084 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2000)	1693 reflections with I > 2σ(I)
T_min = 0.826, T_max = 0.890	R_int = 0.023
4126 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	1 restraint
wR(F²) = 0.105	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.47 e Å⁻³
2084 reflections	Δρ_min = −0.55 e Å⁻³
172 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Symmetry code: (i) −x+1, −y+1, −z.

Hydrogen-bond geometry (Å, º) top

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···N3^iv	0.84	2.01	2.780 (3)	152
O3—H3A···O2	0.87 (1)	1.61 (1)	2.479 (3)	176 (3)

Symmetry codes: (ii) −x, −y+2, −z+1; (iii) x+1, y−1, z; (iv) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[Fe(C₁₀H₆N₃O₄)₂(H₂O)₂]
M_r	556.24
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	7.0100 (14), 8.6670 (17), 9.4110 (19)
α, β, γ (°)	82.28 (3), 83.84 (3), 70.66 (3)
V (Å³)	533.41 (18)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.78
Crystal size (mm)	0.29 × 0.24 × 0.19

Data collection
Diffractometer	Rigaku Mercury CCD diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2000)
T_min, T_max	0.826, 0.890
No. of measured, independent and observed [I > 2σ(I)] reflections	4126, 2084, 1693
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.105, 1.04
No. of reflections	2084
No. of parameters	172
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.47, −0.55

Computer programs: CrystalClear (Rigaku, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O4ⁱ	0.83	2.09	2.852 (3)	152.1
O5—H5A···O3ⁱⁱ	0.89	2.03	2.899 (3)	164.8
O5—H5B···N3ⁱⁱⁱ	0.84	2.01	2.780 (3)	152.1
O3—H3A···O2	0.868 (10)	1.613 (11)	2.479 (3)	176 (3)

Symmetry codes: (i) −x, −y+2, −z+1; (ii) x+1, y−1, z; (iii) −x+1, −y+1, −z+1.

Acknowledgements

This work was supported by the National Natural Science Foundation of China (20771094, 20671083), the Science and Technology Key Task of Henan Province (0524270061) and the China Postdoctoral Science Foundation (20070410877).

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