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

Zhan, Q.-G.

doi:10.1107/S1600536811029618

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page m1186

doi:10.1107/S1600536811029618

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

Qing-Guang Zhan ^a ^*

^aSchool of Chemistry and Environment, South China Normal University, Guangzhou 510006, People's Republic of China, and South China Normal University, Key Laboratory of Technology on Electrochemical Energy Storage and Power Generation in Guangdong Universities, Guangzhou 510006, People's Republic of China
^*Correspondence e-mail: zhanqg2001@yahoo.com.cn

(Received 11 July 2011; accepted 21 July 2011; online 2 August 2011)

In the title complex, [Co(C₁₀H₆N₃O₄)₂(H₂O)₂], the Co^II atom is located on an inversion centre and displays a distorted octahedral coordination geometry defined by two N,O-bidentate ligands in the equatorial plane and two water molecules in the axial positions. The conformation is stabilized by intramolecular O—H⋯O hydrogen bonds. Intermolecular N—H⋯O hydrogen bonds link the molecules into chains, which are further connected by intermolecular O—H⋯O and O—H⋯N hydrogen-bonding interactions, forming a two-dimensional supramolecular network parallel to (110).

Related literature

For general background to the design and synthesis of coordination polymers based on 1H-imidazole-4,5-dicarboxylic acid, see: Gu et al. (2010 ); Wang et al. (2010 ). For related complexes with 5-carboxy-2-(3-pyridyl)-1H-imidazole-4-carboxylate, see: Chen (2008 ); Liu et al. (2009 ); Jing et al. (2010 , 2011 ); Zhou et al. (2011 ).

Experimental

Crystal data

[Co(C₁₀H₆N₃O₄)₂(H₂O)₂]
M_r = 559.32
Triclinic, $[P \overline 1]$
a = 7.0240 (9) Å
b = 8.8770 (12) Å
c = 9.3240 (12) Å
α = 81.598 (2)°
β = 83.290 (2)°
γ = 67.755 (2)°
V = 531.12 (12) Å³
Z = 1
Mo Kα radiation
μ = 0.88 mm⁻¹
T = 298 K
0.32 × 0.28 × 0.26 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.765, T_max = 0.803
2936 measured reflections
2052 independent reflections
1589 reflections with I > 2σ(I)
R_int = 0.017

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.104
S = 1.06
2052 reflections
170 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O2	0.82	1.65	2.465 (3)	176
N2—H2⋯O4ⁱ	0.86	2.00	2.840 (3)	166
O5—H5A⋯O3ⁱⁱ	0.85	2.07	2.918 (3)	173
O5—H5B⋯N3ⁱⁱⁱ	0.85	2.02	2.784 (3)	150
Symmetry codes: (i) -x+1, -y+1, -z+2; (ii) -x+1, -y+1, -z+1; (iii) x, y, z-1.

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811029618/rz2627sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811029618/rz2627Isup2.hkl

checkCIF report

Comment top

In recent years, the design and synthesis of novel metal-organic coordination polymers based on N-heterocyclic carboxylic acids have provoked much attention owing to their structure diversity and their potential applications as functional materials. Particular attention has been paid to the 1H-imidazole-4,5-dicarboxylic acid (H₃IDC) ligand, because it can coordinate with metal ions in diverse coordination fashions to produce a series of complexes with different structures and interesting properties (Gu et al., 2010; Wang et al., 2010). In this work, a very close analogue ligand of H₃IDC, 5-carboxy-2-(3-pyridyl)-1H-imidazole-4-carboxylate (H₃PyIDC), has been chosen to prepare new coordination polymers. Up to now, only two 0D clusters (Chen, 2008; Liu et al., 2009), one 1D chain (Jing et al., 2011), one 2D layer (Zhou et al., 2011), and one 3D network (Jing et al., 2010) constructed by the H₃PyIDC ligand have been reported. For example, Chen (2008) and Liu et al. (2009) have described the structures of the mononuclear complexes [Mn(H₂PyIDC)₂(H₂O)₂] and [Fe(H₂PyIDC)₂(H₂O)₂], in which both the manganese(II) and iron(II) ions show octahedral coordinations with the H₂PyIDC ligands. A new complex [Co(H₂PyIDC)₂(H₂O)₂], (I), which is isostructural with the manganese(II) and iron(II) analogues, is presented in this paper.

As illustrated in Fig. 1, the molecule of (I) is a discrete neutral monomer, with an asymmetric unit that contains one-half of the [Co(H₂PyIDC)₂(H₂O)₂] formula unit. The Co atom lies on an inversion center and is six-coordinated with two nitrogen and two oxygen atoms from two chelating H₂PIDC ligands in the equatorial plane, and two coordinated water molecules in axial positions, forming a slightly distorted octahedral geometry. The Co–N (2.215 (2) Å) and Co–O nond distances (2.061 (2)–2.098 (2)Å) are similar to the M–O and M–N bond lengths ( M = Mn, Fe ) observed in the corresponding isotypic structures. The conformation of the complex is stabilized by intramolecular O—H···O hydrogen bonds. In the crystal structure, intermolecular N–H···O hydrogen bonds (Table 1) link the molecules into one-dimensional chains as shown in Fig. 2. The chains are further connected by two types of hydrogen bonds O–H···O and O–H···N involving the coordinated water molecule, the carboxylate group and the uncoordinated pyridine N atoms, resulting in a two-dimensional supramolecular network (Fig. 3).

Related literature top

For general background to the design and synthesis of coordination polymers based on 1H-imidazole-4,5-dicarboxylic acid, see: Gu et al. (2010); Wang et al. (2010). For related complexes with 5-carboxy-2-(3-pyridyl)-1H-imidazole-4-carboxylate, see: Chen (2008); Liu et al. (2009); Jing et al. (2010, 2011); Zhou et al. (2011).

Experimental top

A mixture of CoCl₂.6H₂O (47.6 mg, 0.2 mmol), H₃PyIDC (46.6 mg, 0.2 mmol), 8 ml H₂O, and 0.1 mL Et₃N was sealed in a 15 mL Teflon-lined stainless steel autoclave, heated at 443 K for 72 h, and then slowly cooled to room temperature at a rate of 5 K h^-1. Brown block-shaped crystals of (I) were obtained with a yield of 28% after washing with distilled water and drying in air.

Computing details top

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

Figures top

	Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level. Unlabelled atoms are related to the labelled atoms by the symmetry operation 2-x, -y, 1-z.
	Fig. 2. Crystal packing of the title compound viewed down the a axis, showing the one-dimensional chain structure. Hydrogen bonds are shown as dashed lines.
	Fig. 3. Crystal packing of the title compound showing the two-dimensional hydrogen-bonding network (dashed lines).

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

Crystal data top

[Co(C₁₀H₆N₃O₄)₂(H₂O)₂]	Z = 1
M_r = 559.32	F(000) = 285
Triclinic, P1	D_x = 1.749 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.0240 (9) Å	Cell parameters from 860 reflections
b = 8.8770 (12) Å	θ = 2.2–24.9°
c = 9.3240 (12) Å	µ = 0.88 mm⁻¹
α = 81.598 (2)°	T = 298 K
β = 83.290 (2)°	Block, brown
γ = 67.755 (2)°	0.32 × 0.28 × 0.26 mm
V = 531.12 (12) Å³

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2052 independent reflections
Radiation source: fine-focus sealed tube	1589 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.017
phi and ω scans	θ_max = 26.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −8→8
T_min = 0.765, T_max = 0.803	k = −10→6
2936 measured reflections	l = −10→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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.104	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0385P)² + 0.3865P] where P = (F_o² + 2F_c²)/3
2052 reflections	(Δ/σ)_max < 0.001
170 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

[Co(C₁₀H₆N₃O₄)₂(H₂O)₂]	γ = 67.755 (2)°
M_r = 559.32	V = 531.12 (12) Å³
Triclinic, P1	Z = 1
a = 7.0240 (9) Å	Mo Kα radiation
b = 8.8770 (12) Å	µ = 0.88 mm⁻¹
c = 9.3240 (12) Å	T = 298 K
α = 81.598 (2)°	0.32 × 0.28 × 0.26 mm
β = 83.290 (2)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2052 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1589 reflections with I > 2σ(I)
T_min = 0.765, T_max = 0.803	R_int = 0.017
2936 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.104	H-atom parameters constrained
S = 1.06	Δρ_max = 0.30 e Å⁻³
2052 reflections	Δρ_min = −0.33 e Å⁻³
170 parameters

Special details top

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 > 2sigma(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
Co1	1.0000	0.0000	0.5000	0.0352 (2)
O3	0.5734 (4)	0.6730 (3)	0.6242 (2)	0.0470 (6)
H3	0.6370	0.6154	0.5601	0.071*
N2	0.6548 (4)	0.2945 (3)	0.8556 (2)	0.0313 (6)
H2	0.5996	0.3198	0.9404	0.038*
O1	0.9299 (4)	0.2412 (3)	0.4017 (2)	0.0432 (6)
N1	0.8176 (4)	0.1439 (3)	0.6778 (2)	0.0310 (6)
O2	0.7771 (4)	0.5056 (3)	0.4308 (2)	0.0463 (6)
O4	0.4586 (4)	0.6330 (3)	0.8526 (2)	0.0511 (7)
C3	0.6630 (5)	0.4031 (4)	0.7370 (3)	0.0309 (7)
C5	0.7482 (5)	0.1401 (4)	0.8172 (3)	0.0295 (7)
O5	0.7336 (3)	−0.0027 (3)	0.4303 (2)	0.0456 (6)
H5A	0.6363	0.0901	0.4178	0.055*
H5B	0.7239	−0.0620	0.3698	0.055*
C4	0.5565 (5)	0.5820 (4)	0.7409 (3)	0.0359 (8)
N3	0.7778 (4)	−0.1290 (3)	1.1669 (3)	0.0395 (7)
C1	0.8292 (5)	0.3538 (4)	0.4769 (3)	0.0358 (8)
C10	0.7591 (5)	−0.0006 (4)	1.0681 (3)	0.0357 (7)
H10	0.7395	0.0988	1.1006	0.043*
C2	0.7669 (5)	0.3071 (4)	0.6286 (3)	0.0307 (7)
C6	0.7672 (5)	−0.0064 (4)	0.9188 (3)	0.0302 (7)
C9	0.8085 (5)	−0.2721 (4)	1.1191 (3)	0.0408 (8)
H9	0.8238	−0.3634	1.1865	0.049*
C8	0.8181 (5)	−0.2887 (4)	0.9732 (3)	0.0413 (8)
H8	0.8411	−0.3901	0.9436	0.050*
C7	0.7934 (5)	−0.1542 (4)	0.8716 (3)	0.0381 (8)
H7	0.7943	−0.1628	0.7732	0.046*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co1	0.0425 (4)	0.0304 (4)	0.0199 (3)	0.0005 (3)	0.0020 (2)	−0.0042 (2)
O3	0.0634 (17)	0.0283 (12)	0.0362 (13)	−0.0031 (12)	0.0034 (12)	−0.0062 (10)
N2	0.0357 (15)	0.0312 (14)	0.0193 (12)	−0.0042 (12)	0.0043 (10)	−0.0056 (10)
O1	0.0519 (15)	0.0365 (13)	0.0219 (11)	0.0020 (11)	0.0086 (10)	−0.0030 (10)
N1	0.0381 (15)	0.0277 (13)	0.0184 (12)	−0.0038 (12)	0.0022 (10)	−0.0016 (10)
O2	0.0629 (16)	0.0325 (13)	0.0277 (12)	−0.0056 (12)	0.0065 (11)	0.0050 (10)
O4	0.0706 (18)	0.0352 (13)	0.0320 (13)	0.0002 (12)	0.0022 (12)	−0.0142 (10)
C3	0.0337 (17)	0.0270 (16)	0.0239 (15)	−0.0026 (13)	0.0012 (12)	−0.0043 (12)
C5	0.0319 (17)	0.0280 (16)	0.0217 (14)	−0.0035 (13)	0.0014 (12)	−0.0047 (12)
O5	0.0465 (14)	0.0443 (14)	0.0339 (12)	−0.0005 (11)	−0.0039 (10)	−0.0109 (10)
C4	0.0436 (19)	0.0300 (17)	0.0261 (16)	−0.0045 (15)	−0.0011 (14)	−0.0043 (14)
N3	0.0473 (17)	0.0373 (16)	0.0261 (13)	−0.0089 (13)	0.0000 (12)	0.0001 (12)
C1	0.0409 (19)	0.0346 (18)	0.0198 (15)	−0.0019 (15)	0.0016 (13)	−0.0014 (13)
C10	0.0412 (19)	0.0343 (18)	0.0261 (15)	−0.0083 (15)	0.0008 (13)	−0.0044 (13)
C2	0.0357 (18)	0.0269 (16)	0.0217 (14)	−0.0036 (14)	0.0010 (12)	−0.0026 (12)
C6	0.0311 (17)	0.0298 (16)	0.0227 (14)	−0.0055 (13)	0.0047 (12)	−0.0025 (12)
C9	0.043 (2)	0.0353 (18)	0.0373 (18)	−0.0102 (16)	−0.0024 (15)	0.0064 (15)
C8	0.050 (2)	0.0316 (18)	0.0390 (19)	−0.0113 (16)	0.0023 (15)	−0.0070 (15)
C7	0.044 (2)	0.0421 (19)	0.0241 (15)	−0.0118 (16)	0.0048 (14)	−0.0074 (14)

Geometric parameters (Å, º) top

Co1—O5ⁱ	2.061 (2)	C3—C2	1.374 (4)
Co1—O5	2.061 (2)	C3—C4	1.481 (4)
Co1—O1	2.098 (2)	C5—C6	1.465 (4)
Co1—O1ⁱ	2.098 (2)	O5—H5A	0.8500
Co1—N1	2.215 (2)	O5—H5B	0.8499
Co1—N1ⁱ	2.215 (2)	N3—C10	1.332 (4)
O3—C4	1.279 (4)	N3—C9	1.339 (4)
O3—H3	0.8200	C1—C2	1.479 (4)
N2—C5	1.358 (4)	C10—C6	1.394 (4)
N2—C3	1.368 (4)	C10—H10	0.9300
N2—H2	0.8600	C6—C7	1.384 (4)
O1—C1	1.243 (4)	C9—C8	1.381 (4)
N1—C5	1.334 (3)	C9—H9	0.9300
N1—C2	1.374 (4)	C8—C7	1.380 (4)
O2—C1	1.276 (4)	C8—H8	0.9300
O4—C4	1.223 (4)	C7—H7	0.9300

O5ⁱ—Co1—O5	180.0	Co1—O5—H5A	115.6
O5ⁱ—Co1—O1	89.88 (10)	Co1—O5—H5B	127.2
O5—Co1—O1	90.12 (10)	H5A—O5—H5B	107.7
O5ⁱ—Co1—O1ⁱ	90.12 (10)	O4—C4—O3	124.5 (3)
O5—Co1—O1ⁱ	89.88 (10)	O4—C4—C3	119.0 (3)
O1—Co1—O1ⁱ	180.0	O3—C4—C3	116.5 (3)
O5ⁱ—Co1—N1	90.05 (9)	C10—N3—C9	117.7 (3)
O5—Co1—N1	89.95 (9)	O1—C1—O2	124.0 (3)
O1—Co1—N1	78.08 (8)	O1—C1—C2	117.3 (3)
O1ⁱ—Co1—N1	101.92 (8)	O2—C1—C2	118.7 (3)
O5ⁱ—Co1—N1ⁱ	89.95 (9)	N3—C10—C6	123.8 (3)
O5—Co1—N1ⁱ	90.05 (9)	N3—C10—H10	118.1
O1—Co1—N1ⁱ	101.92 (8)	C6—C10—H10	118.1
O1ⁱ—Co1—N1ⁱ	78.08 (8)	N1—C2—C3	110.8 (2)
N1—Co1—N1ⁱ	180.00 (7)	N1—C2—C1	119.0 (3)
C4—O3—H3	109.5	C3—C2—C1	130.2 (3)
C5—N2—C3	108.6 (2)	C7—C6—C10	117.7 (3)
C5—N2—H2	125.7	C7—C6—C5	121.9 (3)
C3—N2—H2	125.7	C10—C6—C5	120.4 (3)
C1—O1—Co1	117.58 (19)	N3—C9—C8	122.3 (3)
C5—N1—C2	105.3 (2)	N3—C9—H9	118.9
C5—N1—Co1	146.4 (2)	C8—C9—H9	118.9
C2—N1—Co1	107.94 (17)	C7—C8—C9	119.7 (3)
N2—C3—C2	104.8 (3)	C7—C8—H8	120.1
N2—C3—C4	121.4 (3)	C9—C8—H8	120.1
C2—C3—C4	133.6 (3)	C8—C7—C6	118.7 (3)
N1—C5—N2	110.5 (2)	C8—C7—H7	120.6
N1—C5—C6	126.5 (3)	C6—C7—H7	120.6
N2—C5—C6	123.0 (2)

O5ⁱ—Co1—O1—C1	−88.7 (3)	Co1—O1—C1—C2	−0.4 (4)
O5—Co1—O1—C1	91.3 (3)	C9—N3—C10—C6	0.8 (5)
N1—Co1—O1—C1	1.4 (2)	C5—N1—C2—C3	−1.2 (4)
N1ⁱ—Co1—O1—C1	−178.6 (2)	Co1—N1—C2—C3	−176.6 (2)
O5ⁱ—Co1—N1—C5	−84.2 (4)	C5—N1—C2—C1	178.0 (3)
O5—Co1—N1—C5	95.8 (4)	Co1—N1—C2—C1	2.6 (3)
O1—Co1—N1—C5	−174.0 (4)	N2—C3—C2—N1	1.3 (4)
O1ⁱ—Co1—N1—C5	6.0 (4)	C4—C3—C2—N1	−172.9 (3)
O5ⁱ—Co1—N1—C2	87.8 (2)	N2—C3—C2—C1	−177.8 (3)
O5—Co1—N1—C2	−92.2 (2)	C4—C3—C2—C1	8.0 (6)
O1—Co1—N1—C2	−2.0 (2)	O1—C1—C2—N1	−1.7 (5)
O1ⁱ—Co1—N1—C2	178.0 (2)	O2—C1—C2—N1	178.3 (3)
C5—N2—C3—C2	−0.9 (3)	O1—C1—C2—C3	177.3 (3)
C5—N2—C3—C4	174.2 (3)	O2—C1—C2—C3	−2.7 (6)
C2—N1—C5—N2	0.6 (4)	N3—C10—C6—C7	0.9 (5)
Co1—N1—C5—N2	172.7 (3)	N3—C10—C6—C5	−179.1 (3)
C2—N1—C5—C6	−179.1 (3)	N1—C5—C6—C7	−23.7 (5)
Co1—N1—C5—C6	−7.0 (6)	N2—C5—C6—C7	156.7 (3)
C3—N2—C5—N1	0.2 (4)	N1—C5—C6—C10	156.4 (3)
C3—N2—C5—C6	179.9 (3)	N2—C5—C6—C10	−23.3 (5)
N2—C3—C4—O4	−0.4 (5)	C10—N3—C9—C8	−0.9 (5)
C2—C3—C4—O4	173.0 (4)	N3—C9—C8—C7	−0.7 (5)
N2—C3—C4—O3	−179.9 (3)	C9—C8—C7—C6	2.4 (5)
C2—C3—C4—O3	−6.5 (6)	C10—C6—C7—C8	−2.5 (5)
Co1—O1—C1—O2	179.7 (3)	C5—C6—C7—C8	177.6 (3)

Symmetry code: (i) −x+2, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2	0.82	1.65	2.465 (3)	176
N2—H2···O4ⁱⁱ	0.86	2.00	2.840 (3)	166
O5—H5A···O3ⁱⁱⁱ	0.85	2.07	2.918 (3)	173
O5—H5B···N3^iv	0.85	2.02	2.784 (3)	150

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

Experimental details

Crystal data
Chemical formula	[Co(C₁₀H₆N₃O₄)₂(H₂O)₂]
M_r	559.32
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	7.0240 (9), 8.8770 (12), 9.3240 (12)
α, β, γ (°)	81.598 (2), 83.290 (2), 67.755 (2)
V (Å³)	531.12 (12)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.88
Crystal size (mm)	0.32 × 0.28 × 0.26

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.765, 0.803
No. of measured, independent and observed [I > 2σ(I)] reflections	2936, 2052, 1589
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.104, 1.06
No. of reflections	2052
No. of parameters	170
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.33

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2	0.82	1.65	2.465 (3)	176.0
N2—H2···O4ⁱ	0.86	2.00	2.840 (3)	166.2
O5—H5A···O3ⁱⁱ	0.85	2.07	2.918 (3)	173.0
O5—H5B···N3ⁱⁱⁱ	0.85	2.02	2.784 (3)	149.6

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

Acknowledgements

The authors acknowledge the Young Teacher Training Plan of Guangdong Universities for supporting this work.

References

Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chen, L.-Z. (2008). Acta Cryst. E64, m1286. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gu, Z.-G., Cai, Y.-P., Fang, H.-C., Zhou, Z.-Y., Thallapally, P.-K., Tian, J., Liu, J. & Exarhos, G.-J. (2010). Chem. Commun. 46, 5373–5375. CSD CrossRef CAS Google Scholar
Jing, X.-M., Meng, H., Li, G.-H., Yu, Y., Huo, Q.-S., Eddaoudi, M. & Liu, Y.-L. (2010). Cryst. Growth Des. 10, 3489–3495. Web of Science CSD CrossRef CAS Google Scholar
Jing, X.-M., Zhao, T.-T., Zheng, B., Peng, Y., Yan, Y., Huo, Q.-S. & Liu, Y.-L. (2011). Inorg. Chem. Commun. 14, 22–25. Web of Science CSD CrossRef CAS Google Scholar
Liu, W., Zhang, G., Li, X., Wu, B.-L. & Zhang, H.-Y. (2009). Acta Cryst. E65, m938–m939. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, S., Zhao, T.-T., Li, G.-H., Wojtas, L., Huo, Q.-S., Eddaoudi, M. & Liu, Y.-L. (2010). J. Am. Chem. Soc. 132, 18038–18041. Web of Science CSD CrossRef CAS PubMed Google Scholar
Zhou, R.-S., Song, J.-F., Li, Y.-B., Xu, C.-Y. & Yang, X.-F. (2011). Z. Anorg. Allg. Chem. 637, 251–256. Web of Science CSD CrossRef CAS Google Scholar

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