μ-Pyrazine-bis­[tetra­aqua­cadmium(II)] μ-pyrazine-bis­[tetra­acetato­cadmium(II)]

Fun, H.-K.; Chantrapromma, S.; Marandi, F.

doi:10.1107/S1600536808010994

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 5| May 2008| Pages m736-m737

doi:10.1107/S1600536808010994

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μ-Pyrazine-bis[tetraaquacadmium(II)] μ-pyrazine-bis[tetraacetatocadmium(II)]

Hoong-Kun Fun,^a ^* Suchada Chantrapromma ^b ‡ and Farzin Marandi ^c

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bDepartment of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, and ^cDepartment of Science, Payame Noor University, Zanjan, Iran
^*Correspondence e-mail: hkfun@usm.my

(Received 31 March 2008; accepted 19 April 2008; online 30 April 2008)

In the title dinuclear ionic complex, [Cd₂(C₄H₄N₂)(H₂O)₈][Cd₂(CH₃CO₂)₈(C₄H₄N₂)], the cation and anion are disordered equally over a site with symmetry mmm. The Cd^II ions and the N atoms of the bridging pyrazine ligand lie on the intersection of two crystallographic mirror planes. The C atoms of the bridging pyrazine ligand lie on one of these mirror planes, and the acetate groups and water molecules lie across the intersecting mirror planes. Each Cd^II atom in the cation is five-coordinated by four O atoms from four water molecules and one N atom from the bridging pyrazine ligand, whereas each Cd^II in the anion is nine-coordinated by four pairs of O atoms from the bidentate acetate ligands and one N atom from the bridging pyrazine ligand. In the crystal structure, each anion is surrounded by eight nearest-neighbour cations and vice versa. The crystal structure is stabilized by ionic interactions as well as by C—H⋯O interactions.

Related literature

For bond-length data, see: Allen et al. (1987 ). For Cd^II coordination chemistry, applications and related structures, see: Filipović et al. (2008 ); Inoue et al. (2000 ); Pons et al. (2007 ); Xia et al. (2004 ).

Experimental

Crystal data

[Cd₂(C₄H₄N₂)(H₂O)₈][Cd₂(C₂H₃O₂)₈(C₄H₄N₂)]
M_r = 1226.26
Tetragonal, I 4/m c m
a = 16.7103 (4) Å
c = 7.3533 (2) Å
V = 2053.29 (9) Å³
Z = 2
Mo Kα radiation
μ = 2.13 mm⁻¹
T = 100.0 (1) K
0.58 × 0.08 × 0.05 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.371, T_max = 0.895
12617 measured reflections
1246 independent reflections
1145 reflections with I > 2σ(I)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.016
wR(F²) = 0.034
S = 1.06
1246 reflections
73 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.59 e Å⁻³
Δρ_min = −0.44 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯O2	0.96	2.47	3.0405 (18)	118
C1—H1A⋯O1Wⁱ	0.96	2.56	3.2700 (17)	131
C1—H1A⋯O2ⁱⁱ	0.96	2.47	3.0405 (18)	118
C1—H1A⋯O1Wⁱⁱⁱ	0.96	2.56	3.2700 (17)	131
Symmetry codes: (i) $[-x, y, -z+{\script{1\over 2}}]$ ; (ii) x, y, -z; (iii) $[-x, y, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); 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 and PLATON (Spek, 2003 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808010994/ci2576sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808010994/ci2576Isup2.hkl

checkCIF report

Comment top

The investigations of coordination compounds between cadmium(II) and O and N donors atoms have attracted much attention due to their potential application in a number of areas (Inoue et al., 2000; Pons et al., 2007; Xia et al., 2004), including cytotoxic activities (Filipović et al., 2008). We report herein, the synthesis and crystal structure of the title compound which exhibits a mixed coordination for Cd^II atom i.e nine- and five-coordination mode for Cd^II, which is a rare case.

In the title compound, both [Cd₂(H₂O)₈(C₄H₄N₂)]⁴⁺ cations and [Cd₂(CH₃CO₂)₈(C₄H₄N₂)]^4- anions lie on the site symmetry mmm. The Cd^II and the N atoms of the bridging pyrazine ligand lie on the intersection of two crystallographic mirror planes, one perpenidicular to the c axis (z = 0) and the other parallel to the c axis and passing through the mid points of the a and b axis. The C atoms of the bridging pyrazine ligand lie on the z = 0 mirror plane, and the acetate groups and water molecules lie across the intersecting mirror planes. There are two molecules of the title complex in the unit cell.

In the structure, the cation contains two Cd^II ions, eight water molecules and one bridging pyrazine ligand whereas the anion contains two Cd^II ions, eight acetate and one bridging pyrazine ligands. Each of the Cd^II in the cation is five-coordinated with four O atoms from four water molecules and one N atom from a bridging pyrazine ligand, whereas each Cd^II in the anion is nine-coordinated with four pairs of chelate O atoms from the bidentate acetate ligands and one N atom from the bridging pyrazine ligand. The Cd—O(acetate) bond distances are 2.3458 (14) and 2.5200 (14) Å, and the Cd—O(water) and Cd—N distances are 2.2783 (15) Å and 2.3470 (15) Å, respectively. The O(water)—Cd—O(water) bond angles lie in the range 64.15 (8)°-174.10 (7)°, whereas, the O(acetate)—Cd—O(acetate) bond angles are in the range 53.57 (7)°-158.87 (6)°. The N—Cd—O(water) angle is 92.95 (3)° and N—Cd—O(acetate) angles are 132.77 (3)° and 79.43 (3)°, respectively. The geometric parameters are comparable to those reported for other Cd—O and Cd—N donor complexes (Inoue et al., 2000; Pons et al., 2007; Xia et al., 2004).

In the crystal packing (Fig. 2 and Fig.3), each anion is surrounded by eight nearest neighbour cations and vice-versa. The crystal structure is stablized by ionic interactions as well as by weak C—H···O interactions (Table 1).

Related literature top

For bond length data, see: Allen et al. (1987). For Cd^II coordination chemistry and applications, see: Filipović et al. (2008); Inoue et al. (2000); Pons et al. (2007); Xia et al. (2004). For related structures, see: Inoue et al. (2000); Pons et al. (2007); Xia et al. (2004).

Experimental top

The title compound was synthesized by mixing Cd(CH₃COO)₂ and pyrazine with a 2:1 molar ratio in a hot methanol-water (2:1 v/v) solution and stirred for 10 min at room temperature. The solution was then left at ambient temperature to allow the solvent to slowly evaporate. Colourless crystals of the title compound suitable for X-ray structure determination were obtained after a few weeks.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (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) and PLATON (Spek, 2003).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atomic numbering. The cations and anions occupy the same site with equal occupancy. Symmetry codes for the Cd1A ion: (A) -x, 1 - y, -z. Symmetry codes for aqua and acetate atoms: (A) x, y, -z; (B) 1/2 - y, 1/2 - x, z; (C) 1/2 - y, 1/2 - x, -z; (D) y - 1/2, 1/2 + x, -z; (E) y - 1/2, 1/2 + x, z; (F) -x, 1 - y, -z; (G) -x, 1 - y, z. Symmetry codes for ring C atoms: (A) 1/2 - y, 1/2 - x, z; (B) y - 1/2, 1/2 + x, -z; (C) -x, 1 - y, -z. Symmetry code for the N1 atom: (A) -x, 1 - y, -z.
	Fig. 2. The crystal packing of the title compound, viewed along the c axis, showing a layer of the cations and anions.
	Fig. 3. The crystal packing of the title compound, viewed along the a axis, showing the same layer of cations and anions in Fig. 2.

µ-Pyrazine-bis[tetraaquacadmium(II)] µ-pyrazine-bis[tetraacetatocadmium(II)] top

Crystal data top

[Cd₂(C₄H₄N₂)(H₂O)₈][Cd₂(C₂H₃O₂)₈(C₄H₄N₂)]	D_x = 1.983 Mg m⁻³
M_r = 1226.26	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, I4/mcm	Cell parameters from 1246 reflections
Hall symbol: -I 4 2c	θ = 1.7–35.0°
a = 16.7103 (4) Å	µ = 2.13 mm⁻¹
c = 7.3533 (2) Å	T = 100 K
V = 2053.29 (9) Å³	Needle, colourless
Z = 2	0.58 × 0.08 × 0.05 mm
F(000) = 1208

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	1246 independent reflections
Radiation source: fine-focus sealed tube	1145 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.037
Detector resolution: 8.33 pixels mm^-1	θ_max = 35.0°, θ_min = 1.7°
ω scans	h = −26→26
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −26→26
T_min = 0.371, T_max = 0.895	l = −11→11
12617 measured reflections

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)] = 0.016	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.034	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0089P)² + 1.5621P] where P = (F_o² + 2F_c²)/3
1246 reflections	(Δ/σ)_max = 0.002
73 parameters	Δρ_max = 0.59 e Å⁻³
2 restraints	Δρ_min = −0.44 e Å⁻³

Crystal data top

[Cd₂(C₄H₄N₂)(H₂O)₈][Cd₂(C₂H₃O₂)₈(C₄H₄N₂)]	Z = 2
M_r = 1226.26	Mo Kα radiation
Tetragonal, I4/mcm	µ = 2.13 mm⁻¹
a = 16.7103 (4) Å	T = 100 K
c = 7.3533 (2) Å	0.58 × 0.08 × 0.05 mm
V = 2053.29 (9) Å³

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	1246 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1145 reflections with I > 2σ(I)
T_min = 0.371, T_max = 0.895	R_int = 0.037
12617 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.016	2 restraints
wR(F²) = 0.034	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.59 e Å⁻³
1246 reflections	Δρ_min = −0.44 e Å⁻³
73 parameters

Special details top

Experimental. The data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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	Occ. (<1)
Cd1	0.158218 (5)	0.341782 (5)	0.0000	0.01214 (4)
O1	0.16811 (7)	0.21686 (8)	0.1438 (2)	0.0156 (2)	0.50
O2	0.04830 (8)	0.27097 (9)	0.1708 (2)	0.0183 (3)	0.50
C2	0.09773 (11)	0.21621 (11)	0.2069 (3)	0.0144 (3)	0.50
C3	0.07138 (12)	0.14714 (12)	0.3238 (3)	0.0212 (4)	0.50
H3A	0.0344	0.1659	0.4142	0.036 (9)*	0.50
H3B	0.1172	0.1240	0.3825	0.038 (8)*	0.50
H3C	0.0458	0.1075	0.2493	0.031 (8)*	0.50
O1W	0.11198 (8)	0.28563 (8)	0.2621 (2)	0.0170 (3)	0.50
H1W1	0.0654 (4)	0.2746 (17)	0.262 (4)	0.020 (7)*	0.50
H2W1	0.1447 (16)	0.2523 (16)	0.287 (5)	0.055 (11)*	0.50
N1	0.05890 (6)	0.44110 (6)	0.0000	0.0131 (3)
C1	−0.01905 (7)	0.42237 (7)	0.0000	0.0144 (2)
H1A	−0.0354	0.3673	0.0000	0.017*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cd1	0.00955 (4)	0.00955 (4)	0.01731 (7)	0.00080 (4)	0.000	0.000
O1	0.0119 (5)	0.0133 (5)	0.0216 (7)	0.0003 (4)	0.0008 (5)	0.0015 (5)
O2	0.0137 (6)	0.0151 (6)	0.0260 (8)	0.0028 (5)	0.0007 (6)	0.0037 (5)
C2	0.0131 (7)	0.0118 (7)	0.0181 (8)	−0.0016 (5)	−0.0025 (6)	0.0004 (6)
C3	0.0189 (9)	0.0195 (9)	0.0251 (10)	−0.0014 (7)	0.0006 (7)	0.0074 (8)
O1W	0.0121 (5)	0.0156 (6)	0.0233 (7)	0.0022 (5)	0.0023 (5)	0.0030 (5)
N1	0.0119 (4)	0.0119 (4)	0.0155 (7)	0.0010 (5)	0.000	0.000
C1	0.0122 (5)	0.0113 (5)	0.0196 (6)	0.0004 (4)	0.000	0.000

Geometric parameters (Å, º) top

Cd1—O1W	2.2782 (15)	O1—C2	1.264 (2)
Cd1—O1Wⁱ	2.2783 (15)	O2—C2	1.261 (2)
Cd1—O1Wⁱⁱ	2.2783 (15)	C2—C3	1.505 (3)
Cd1—O1Wⁱⁱⁱ	2.2783 (15)	C3—H3A	0.96
Cd1—O1	2.3458 (14)	C3—H3B	0.96
Cd1—O1ⁱ	2.3458 (14)	C3—H3C	0.96
Cd1—O1ⁱⁱ	2.3458 (14)	O1W—H1W1	0.800 (1)
Cd1—O1ⁱⁱⁱ	2.3458 (14)	O1W—H2W1	0.800 (1)
Cd1—N1	2.3470 (15)	N1—C1ⁱ	1.3396 (15)
Cd1—O2ⁱ	2.5200 (14)	N1—C1	1.3397 (15)
Cd1—O2ⁱⁱ	2.5200 (14)	C1—C1^iv	1.384 (2)
Cd1—O2	2.5200 (14)	C1—H1A	0.96

O1W—Cd1—O1Wⁱ	64.15 (8)	O1ⁱ—Cd1—O2ⁱⁱ	81.84 (5)
O1W—Cd1—O1Wⁱⁱ	174.10 (7)	O1ⁱⁱ—Cd1—O2ⁱⁱ	53.77 (4)
O1Wⁱ—Cd1—O1Wⁱⁱ	115.52 (8)	O1ⁱⁱⁱ—Cd1—O2ⁱⁱ	113.02 (5)
O1W—Cd1—O1Wⁱⁱⁱ	115.51 (8)	N1—Cd1—O2ⁱⁱ	79.43 (3)
O1Wⁱ—Cd1—O1Wⁱⁱⁱ	174.10 (7)	O2ⁱ—Cd1—O2ⁱⁱ	59.77 (8)
O1Wⁱⁱ—Cd1—O1Wⁱⁱⁱ	64.15 (8)	O1—Cd1—O2	53.77 (4)
O1—Cd1—O1ⁱ	70.82 (6)	O1ⁱ—Cd1—O2	113.02 (5)
O1—Cd1—O1ⁱⁱ	94.46 (6)	O1ⁱⁱ—Cd1—O2	147.15 (4)
O1ⁱ—Cd1—O1ⁱⁱ	53.57 (7)	O1ⁱⁱⁱ—Cd1—O2	81.84 (5)
O1—Cd1—O1ⁱⁱⁱ	53.57 (7)	N1—Cd1—O2	79.43 (3)
O1ⁱ—Cd1—O1ⁱⁱⁱ	94.46 (6)	O2ⁱ—Cd1—O2	115.86 (8)
O1ⁱⁱ—Cd1—O1ⁱⁱⁱ	70.82 (6)	O2ⁱⁱ—Cd1—O2	158.87 (6)
O1W—Cd1—N1	92.95 (3)	C2—O1—Cd1	96.17 (11)
O1Wⁱ—Cd1—N1	92.95 (3)	C2—O2—Cd1	88.18 (11)
O1Wⁱⁱ—Cd1—N1	92.95 (3)	O2—C2—O1	121.73 (17)
O1Wⁱⁱⁱ—Cd1—N1	92.95 (3)	O2—C2—C3	119.02 (16)
O1—Cd1—N1	132.77 (3)	O1—C2—C3	119.23 (16)
O1ⁱ—Cd1—N1	132.77 (3)	Cd1—O1W—H1W1	115 (2)
O1ⁱⁱ—Cd1—N1	132.77 (3)	Cd1—O1W—H2W1	104 (3)
O1ⁱⁱⁱ—Cd1—N1	132.77 (3)	H1W1—O1W—H2W1	120 (3)
O1—Cd1—O2ⁱ	113.02 (5)	C1ⁱ—N1—C1	117.01 (15)
O1ⁱ—Cd1—O2ⁱ	53.77 (4)	C1ⁱ—N1—Cd1	121.49 (8)
O1ⁱⁱ—Cd1—O2ⁱ	81.84 (5)	C1—N1—Cd1	121.49 (8)
O1ⁱⁱⁱ—Cd1—O2ⁱ	147.15 (4)	N1—C1—C1^iv	121.50 (8)
N1—Cd1—O2ⁱ	79.43 (3)	N1—C1—H1A	120.0
O1—Cd1—O2ⁱⁱ	147.15 (4)	C1^iv—C1—H1A	118.5

O1ⁱ—Cd1—O1—C2	137.93 (10)	O1Wⁱⁱⁱ—Cd1—N1—C1ⁱ	−122.12 (4)
O1ⁱⁱ—Cd1—O1—C2	−173.19 (14)	O1—Cd1—N1—C1ⁱ	142.13 (5)
O1ⁱⁱⁱ—Cd1—O1—C2	−111.03 (11)	O1ⁱ—Cd1—N1—C1ⁱ	37.87 (5)
N1—Cd1—O1—C2	6.81 (14)	O1ⁱⁱ—Cd1—N1—C1ⁱ	−37.87 (5)
O2ⁱ—Cd1—O1—C2	103.79 (12)	O1ⁱⁱⁱ—Cd1—N1—C1ⁱ	−142.13 (5)
O2ⁱⁱ—Cd1—O1—C2	173.28 (11)	O2ⁱ—Cd1—N1—C1ⁱ	30.46 (4)
O2—Cd1—O1—C2	−2.25 (11)	O2ⁱⁱ—Cd1—N1—C1ⁱ	−30.46 (4)
O1—Cd1—O2—C2	2.24 (11)	O2—Cd1—N1—C1ⁱ	149.54 (4)
O1ⁱ—Cd1—O2—C2	−38.85 (13)	O1W—Cd1—N1—C1	−57.88 (4)
O1ⁱⁱ—Cd1—O2—C2	19.05 (17)	O1Wⁱ—Cd1—N1—C1	−122.12 (4)
O1ⁱⁱⁱ—Cd1—O2—C2	52.55 (12)	O1Wⁱⁱ—Cd1—N1—C1	122.12 (4)
N1—Cd1—O2—C2	−171.01 (12)	O1Wⁱⁱⁱ—Cd1—N1—C1	57.88 (4)
O2ⁱ—Cd1—O2—C2	−98.33 (12)	O1—Cd1—N1—C1	−37.87 (5)
O2ⁱⁱ—Cd1—O2—C2	−171.01 (12)	O1ⁱ—Cd1—N1—C1	−142.13 (5)
Cd1—O2—C2—O1	−3.94 (19)	O1ⁱⁱ—Cd1—N1—C1	142.13 (5)
Cd1—O2—C2—C3	177.83 (17)	O1ⁱⁱⁱ—Cd1—N1—C1	37.87 (5)
Cd1—O1—C2—O2	4.3 (2)	O2ⁱ—Cd1—N1—C1	−149.54 (4)
Cd1—O1—C2—C3	−177.52 (16)	O2ⁱⁱ—Cd1—N1—C1	149.54 (4)
O1W—Cd1—N1—C1ⁱ	122.12 (4)	O2—Cd1—N1—C1	−30.46 (4)
O1Wⁱ—Cd1—N1—C1ⁱ	57.88 (4)	C1ⁱ—N1—C1—C1^iv	0.0
O1Wⁱⁱ—Cd1—N1—C1ⁱ	−57.88 (4)	Cd1—N1—C1—C1^iv	180.0

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···O2	0.96	2.47	3.0405 (18)	118
C1—H1A···O1W^v	0.96	2.56	3.2700 (17)	131
C1—H1A···O2ⁱⁱⁱ	0.96	2.47	3.0405 (18)	118
C1—H1A···O1W^vi	0.96	2.56	3.2700 (17)	131

Symmetry codes: (iii) x, y, −z; (v) −x, y, −z+1/2; (vi) −x, y, z−1/2.

Experimental details

Crystal data
Chemical formula	[Cd₂(C₄H₄N₂)(H₂O)₈][Cd₂(C₂H₃O₂)₈(C₄H₄N₂)]
M_r	1226.26
Crystal system, space group	Tetragonal, I4/mcm
Temperature (K)	100
a, c (Å)	16.7103 (4), 7.3533 (2)
V (Å³)	2053.29 (9)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.13
Crystal size (mm)	0.58 × 0.08 × 0.05

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.371, 0.895
No. of measured, independent and observed [I > 2σ(I)] reflections	12617, 1246, 1145
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.807

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.016, 0.034, 1.06
No. of reflections	1246
No. of parameters	73
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.59, −0.44

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···O2	0.96	2.47	3.0405 (18)	118
C1—H1A···O1Wⁱ	0.96	2.56	3.2700 (17)	131
C1—H1A···O2ⁱⁱ	0.96	2.47	3.0405 (18)	118
C1—H1A···O1Wⁱⁱⁱ	0.96	2.56	3.2700 (17)	131

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

Footnotes

‡Additional correspondence author, e-mail: suchada.c@psu.ac.th.

Acknowledgements

The authors thank the Malaysian Government and Universiti Sains Malaysia for the Scientific Advancement Grant Allocation (SAGA) grant No. 304/PFIZIK/653003/A118. SC thanks Prince of Songkla University for generous support.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–S19. CrossRef Web of Science Google Scholar
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Filipović, N. R., Bacchi, A., Lazić, M., Pelizzi, G., Radulović, S., Sladić, D., Todorović, T. R. & Andelković, K. K. (2008). Inorg. Chem. Commun. 11, 47–50. Google Scholar
Inoue, M. B., Muñoz, I. C., Inoue, M. & Fernando, Q. (2000). Inorg. Chim. Acta, 300–302, 206–211. Web of Science CSD CrossRef CAS Google Scholar
Pons, J., García-Antón, J., Jiménez, R., Solans, X., Font-Bardia, M. & Ros, J. (2007). Inorg. Chem. Commun. 10, 1554–1556. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar
Xia, S.-Q., Hu, S.-M., Dai, J.-C., Wu, X.-T., Fu, Z.-Y., Zhang, J.-J. & Du, W.-X. (2004). Polyhedron, 23, 1003–1009. Web of Science CSD CrossRef CAS Google Scholar

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