catena-Poly[diaqua­(cis-cyclo­hexane-1,2-dicarboxyl­ato)cadmium]

Zhu, X.-H.; Cheng, X.-C.

doi:10.1107/S1600536811044187

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page m1617

doi:10.1107/S1600536811044187

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catena-Poly[diaqua(cis-cyclohexane-1,2-dicarboxylato)cadmium]

Xiao-Hong Zhu ^a ^* and Xiao-Chun Cheng ^a

^aFaculty of Life Science and Chemical Engineering, Huaiyin Institute of Technology, Huaian 223003, People's Republic of China
^*Correspondence e-mail: hgzhuxh@yeah.net

(Received 2 October 2011; accepted 24 October 2011; online 29 October 2011)

In the title polymer, [Cd(C₈H₁₀O₄)(H₂O)₂]_n, the Cd^II cation is coordinated by five carboxylate O atoms from three different cyclohexane-1,2-dicarboxylate anions and two O atoms from two water molecules, displaying a distorted CdO₇ pentagonal–bipyramidal geometry. Each anion acts as a μ₃-bridge, linking symmetry-related Cd^II ions into a layer parallel to (010). In the crystal, numerous O—H⋯O and C—H⋯O hydrogen bonds occur. The coordinated water molecules and carboxylate O atoms act as donors or acceptors in the formation of these hydrogen-bonding interactions.

Related literature

For related structures, see: Thirumurugan et al. (2006 ).

Experimental

Crystal data

[Cd(C₈H₁₀O₄)(H₂O)₂]
M_r = 318.59
Monoclinic, P 2₁ /c
a = 6.0585 (9) Å
b = 23.544 (3) Å
c = 8.3308 (9) Å
β = 118.787 (8)°
V = 1041.5 (2) Å³
Z = 4
Mo Kα radiation
μ = 2.10 mm⁻¹
T = 293 K
0.20 × 0.20 × 0.18 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.678, T_max = 0.703
5908 measured reflections
2250 independent reflections
2214 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.062
wR(F²) = 0.132
S = 1.51
2250 reflections
136 parameters
H-atom parameters constrained
Δρ_max = 1.31 e Å⁻³
Δρ_min = −2.11 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H11⋯O6ⁱ	0.85	2.01	2.828 (8)	164
O5—H12⋯O4ⁱⁱ	0.85	1.89	2.725 (8)	169
O6—H13⋯O3ⁱⁱⁱ	0.85	1.85	2.694 (8)	175
O6—H14⋯O2^iv	0.84	2.49	3.147 (8)	136
O6—H14⋯O4^iv	0.84	2.57	3.016 (8)	115
C3—H3⋯O2	0.97	2.59	3.120 (10)	115
C6—H9⋯O4^v	0.97	2.30	3.257 (10)	169
Symmetry codes: (i) $[x-1, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iii) x+1, y, z; (iv) $[x+1, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (v) x+1, y, z+1.

Data collection: APEX2 (Bruker, 2008 ); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2000 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811044187/pv2458sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811044187/pv2458Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811044187/pv2458Isup3.cdx

checkCIF report

Comment top

cyclohexane-1,2-dicarboxylic acid is often used as organic ligand to synthesize complexes for its variable conformation and coordination modes. Herein, we report the crystal structure of the title polymer. In contrast to the reported cadmium complex with cyclohexane-1,2-dicarboxylate (Thirumurugan et al., 2006), the title complex crystallizes in a different space group, besides different carboxylate coordination modes and different crystal structure. The asymmetric unit of the title complex (Fig. 1) consists of a cadmium ion, a cyclohexane-1,2-dicarboxylate anion, and two coordinated water molecules. The Cd ion is coordinated by five carboxylate O atoms from three different cyclohexane-1,2-dicarboxylate anions, two O atoms from two coordinated water molecules, displaying a distorted CdO₇ decahedral geometry. Each anion acts as a µ₃-bridge, linking different cadmium ions to form a two-dimensional layer. In the crystal structure, there exist abundant O—H···O and C—H···O hydrogen bonds (Table 1, Fig. 1). Coordinated water molecules and carboxylate oxygen atoms act as donors or acceptors in the formation of these hydrogen bonding interactions.

Related literature top

For related structures, see: Thirumurugan et al. (2006).

Experimental top

Reaction mixture of cadmium perchlorate hexahydrate (49.4 mg, 0.1 mmol), cyclohexane-1,2-dicarboxylic acid (17.2 mg, 0.1 mmol) and potassium hydroxide (11.2 mg, 0.2 mmol) in 12 ml H₂O was sealed in a 16 ml Teflon-lined stainless steel container and heated to 393 K for 3 days. After cooling to room temperature, colorless block crystals of the title complex were obtained.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2000); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. : The coordination environment of Cd ion in the title complex with the ellipsoids drawn at the 30% probability level. The hydrogen atoms are omitted for clarity. Symmetry code: A = 1 + x, 3/2 - y, 1/2 + z; B = x, 3/2 - y, 1/2 + z.
	Fig. 2. : The packing diagram of the title complex. Hydrogen bonds are shown in dashed lines.

catena-Poly[diaqua(cis-cyclohexane-1,2-dicarboxylato)cadmium] top

Crystal data top

[Cd(C₈H₁₀O₄)(H₂O)₂]	F(000) = 632
M_r = 318.59	D_x = 2.032 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3464 reflections
a = 6.0585 (9) Å	θ = 2.9–28.3°
b = 23.544 (3) Å	µ = 2.10 mm⁻¹
c = 8.3308 (9) Å	T = 293 K
β = 118.787 (8)°	Block, colorless
V = 1041.5 (2) Å³	0.20 × 0.20 × 0.18 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD diffractometer	2250 independent reflections
Radiation source: fine-focus sealed tube	2214 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
phi and ω scans	θ_max = 27.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→7
T_min = 0.678, T_max = 0.703	k = −30→22
5908 measured reflections	l = −9→10

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.132	H-atom parameters constrained
S = 1.51	w = 1/[σ²(F_o²) + (0.0226P)² + 8.9495P] where P = (F_o² + 2F_c²)/3
2250 reflections	(Δ/σ)_max = 0.001
136 parameters	Δρ_max = 1.31 e Å⁻³
0 restraints	Δρ_min = −2.11 e Å⁻³

Crystal data top

[Cd(C₈H₁₀O₄)(H₂O)₂]	V = 1041.5 (2) Å³
M_r = 318.59	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 6.0585 (9) Å	µ = 2.10 mm⁻¹
b = 23.544 (3) Å	T = 293 K
c = 8.3308 (9) Å	0.20 × 0.20 × 0.18 mm
β = 118.787 (8)°

Data collection top

Bruker SMART APEXII CCD diffractometer	2250 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2214 reflections with I > 2σ(I)
T_min = 0.678, T_max = 0.703	R_int = 0.021
5908 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.062	0 restraints
wR(F²) = 0.132	H-atom parameters constrained
S = 1.51	Δρ_max = 1.31 e Å⁻³
2250 reflections	Δρ_min = −2.11 e Å⁻³
136 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
C1	0.2430 (14)	0.8769 (3)	0.3235 (9)	0.0215 (15)
H1	0.1239	0.8731	0.3710	0.026*
C2	0.0977 (14)	0.9021 (3)	0.1294 (9)	0.0217 (15)
H2	0.0117	0.9360	0.1402	0.026*
C3	0.2681 (16)	0.9226 (4)	0.0541 (11)	0.0306 (18)
H4	0.1677	0.9430	−0.0595	0.037*
H3	0.3423	0.8900	0.0268	0.037*
C4	0.4788 (18)	0.9615 (4)	0.1884 (13)	0.040 (2)
H6	0.5925	0.9702	0.1405	0.048*
H5	0.4067	0.9969	0.2011	0.048*
C5	0.6240 (16)	0.9336 (4)	0.3738 (12)	0.038 (2)
H7	0.7527	0.9594	0.4574	0.046*
H8	0.7071	0.8998	0.3625	0.046*
C6	0.4523 (17)	0.9175 (3)	0.4512 (11)	0.0324 (19)
H10	0.3772	0.9516	0.4694	0.039*
H9	0.5506	0.8994	0.5694	0.039*
C11	0.3489 (12)	0.8179 (3)	0.3255 (9)	0.0172 (13)
C21	−0.1078 (14)	0.8624 (3)	0.0000 (10)	0.0233 (15)
Cd1	0.52611 (10)	0.71211 (2)	0.27582 (7)	0.02114 (18)
O1	0.4616 (10)	0.7907 (2)	0.4755 (7)	0.0292 (12)
O2	0.3166 (11)	0.7961 (2)	0.1782 (7)	0.0286 (12)
O3	−0.2409 (10)	0.8354 (2)	0.0540 (7)	0.0276 (12)
O4	−0.1527 (11)	0.8576 (3)	−0.1638 (7)	0.0306 (13)
O5	0.1442 (11)	0.6699 (3)	0.1849 (8)	0.0420 (16)
H11	0.0396	0.6864	0.0873	0.050*
H12	0.0655	0.6580	0.2390	0.050*
O6	0.8811 (10)	0.7702 (2)	0.3509 (7)	0.0291 (12)
H13	0.8529	0.7914	0.2610	0.035*
H14	0.9968	0.7461	0.3832	0.035*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.026 (4)	0.018 (4)	0.018 (3)	0.002 (3)	0.009 (3)	0.000 (3)
C2	0.024 (4)	0.019 (3)	0.016 (3)	0.003 (3)	0.005 (3)	0.000 (3)
C3	0.034 (4)	0.029 (4)	0.026 (4)	−0.009 (3)	0.012 (3)	0.003 (3)
C4	0.042 (5)	0.034 (5)	0.047 (5)	−0.014 (4)	0.023 (5)	0.002 (4)
C5	0.021 (4)	0.034 (5)	0.041 (5)	−0.001 (3)	0.001 (4)	0.000 (4)
C6	0.039 (5)	0.022 (4)	0.024 (4)	0.002 (3)	0.006 (4)	−0.005 (3)
C11	0.015 (3)	0.016 (3)	0.020 (3)	−0.001 (3)	0.007 (3)	−0.002 (3)
C21	0.020 (3)	0.022 (4)	0.019 (3)	0.004 (3)	0.003 (3)	−0.001 (3)
Cd1	0.0190 (3)	0.0229 (3)	0.0189 (3)	0.0022 (2)	0.0070 (2)	0.0012 (2)
O1	0.031 (3)	0.031 (3)	0.022 (3)	0.006 (2)	0.011 (2)	0.005 (2)
O2	0.031 (3)	0.030 (3)	0.021 (3)	0.006 (2)	0.010 (2)	−0.003 (2)
O3	0.026 (3)	0.030 (3)	0.030 (3)	−0.007 (2)	0.017 (2)	−0.003 (2)
O4	0.029 (3)	0.039 (3)	0.019 (3)	0.000 (3)	0.007 (2)	0.001 (2)
O5	0.030 (3)	0.064 (4)	0.027 (3)	−0.006 (3)	0.010 (3)	0.014 (3)
O6	0.023 (3)	0.034 (3)	0.028 (3)	0.000 (2)	0.010 (2)	0.007 (2)

Geometric parameters (Å, º) top

C1—C11	1.528 (9)	C11—O1	1.271 (9)
C1—C6	1.534 (11)	C21—O4	1.262 (9)
C1—C2	1.540 (10)	C21—O3	1.266 (9)
C1—H1	0.9800	C21—Cd1ⁱ	2.737 (7)
C2—C21	1.515 (10)	Cd1—O2	2.278 (5)
C2—C3	1.522 (11)	Cd1—O5	2.286 (6)
C2—H2	0.9800	Cd1—O3ⁱⁱ	2.337 (5)
C3—C4	1.531 (11)	Cd1—O1ⁱⁱⁱ	2.340 (5)
C3—H4	0.9700	Cd1—O6	2.365 (5)
C3—H3	0.9700	Cd1—O4ⁱⁱ	2.407 (6)
C4—C5	1.512 (12)	Cd1—O1	2.639 (6)
C4—H6	0.9700	Cd1—C21ⁱⁱ	2.737 (7)
C4—H5	0.9700	O1—Cd1^iv	2.340 (5)
C5—C6	1.512 (13)	O3—Cd1ⁱ	2.337 (5)
C5—H7	0.9700	O4—Cd1ⁱ	2.407 (6)
C5—H8	0.9700	O5—H11	0.8466
C6—H10	0.9700	O5—H12	0.8458
C6—H9	0.9700	O6—H13	0.8460
C11—O2	1.256 (9)	O6—H14	0.8404

C11—C1—C6	110.9 (6)	O3—C21—Cd1ⁱ	58.4 (4)
C11—C1—C2	112.8 (6)	C2—C21—Cd1ⁱ	178.1 (5)
C6—C1—C2	110.6 (6)	O2—Cd1—O5	87.6 (2)
C11—C1—H1	107.4	O2—Cd1—O3ⁱⁱ	137.40 (19)
C6—C1—H1	107.4	O5—Cd1—O3ⁱⁱ	98.8 (2)
C2—C1—H1	107.4	O2—Cd1—O1ⁱⁱⁱ	82.2 (2)
C21—C2—C3	113.0 (6)	O5—Cd1—O1ⁱⁱⁱ	90.7 (2)
C21—C2—C1	111.5 (6)	O3ⁱⁱ—Cd1—O1ⁱⁱⁱ	139.2 (2)
C3—C2—C1	113.4 (6)	O2—Cd1—O6	82.6 (2)
C21—C2—H2	106.1	O5—Cd1—O6	170.2 (2)
C3—C2—H2	106.1	O3ⁱⁱ—Cd1—O6	88.65 (19)
C1—C2—H2	106.1	O1ⁱⁱⁱ—Cd1—O6	87.78 (19)
C2—C3—C4	112.4 (7)	O2—Cd1—O4ⁱⁱ	157.3 (2)
C2—C3—H4	109.1	O5—Cd1—O4ⁱⁱ	111.1 (2)
C4—C3—H4	109.1	O3ⁱⁱ—Cd1—O4ⁱⁱ	54.90 (18)
C2—C3—H3	109.1	O1ⁱⁱⁱ—Cd1—O4ⁱⁱ	84.63 (19)
C4—C3—H3	109.1	O6—Cd1—O4ⁱⁱ	78.4 (2)
H4—C3—H3	107.9	O2—Cd1—O1	52.46 (17)
C5—C4—C3	110.9 (7)	O5—Cd1—O1	94.6 (2)
C5—C4—H6	109.5	O3ⁱⁱ—Cd1—O1	84.97 (17)
C3—C4—H6	109.5	O1ⁱⁱⁱ—Cd1—O1	133.97 (13)
C5—C4—H5	109.5	O6—Cd1—O1	79.61 (19)
C3—C4—H5	109.5	O4ⁱⁱ—Cd1—O1	134.15 (17)
H6—C4—H5	108.0	O2—Cd1—C21ⁱⁱ	158.3 (2)
C4—C5—C6	111.3 (7)	O5—Cd1—C21ⁱⁱ	107.8 (2)
C4—C5—H7	109.4	O3ⁱⁱ—Cd1—C21ⁱⁱ	27.5 (2)
C6—C5—H7	109.4	O1ⁱⁱⁱ—Cd1—C21ⁱⁱ	112.0 (2)
C4—C5—H8	109.4	O6—Cd1—C21ⁱⁱ	81.7 (2)
C6—C5—H8	109.4	O4ⁱⁱ—Cd1—C21ⁱⁱ	27.4 (2)
H7—C5—H8	108.0	O1—Cd1—C21ⁱⁱ	109.6 (2)
C5—C6—C1	111.7 (7)	C11—O1—Cd1^iv	143.0 (5)
C5—C6—H10	109.3	C11—O1—Cd1	84.6 (4)
C1—C6—H10	109.3	Cd1^iv—O1—Cd1	130.9 (2)
C5—C6—H9	109.3	C11—O2—Cd1	102.0 (4)
C1—C6—H9	109.3	C21—O3—Cd1ⁱ	94.1 (4)
H10—C6—H9	107.9	C21—O4—Cd1ⁱ	91.0 (5)
O2—C11—O1	120.8 (6)	Cd1—O5—H11	106.8
O2—C11—C1	119.6 (6)	Cd1—O5—H12	135.0
O1—C11—C1	119.6 (6)	H11—O5—H12	108.1
O4—C21—O3	119.8 (7)	Cd1—O6—H13	109.7
O4—C21—C2	119.9 (7)	Cd1—O6—H14	101.8
O3—C21—C2	120.2 (7)	H13—O6—H14	117.6
O4—C21—Cd1ⁱ	61.6 (4)

C11—C1—C2—C21	54.4 (8)	O3ⁱⁱ—Cd1—O1—C11	176.1 (4)
C6—C1—C2—C21	179.2 (6)	O1ⁱⁱⁱ—Cd1—O1—C11	9.9 (6)
C11—C1—C2—C3	−74.6 (8)	O6—Cd1—O1—C11	86.6 (4)
C6—C1—C2—C3	50.2 (9)	O4ⁱⁱ—Cd1—O1—C11	149.0 (4)
C21—C2—C3—C4	−178.5 (7)	C21ⁱⁱ—Cd1—O1—C11	163.8 (4)
C1—C2—C3—C4	−50.3 (9)	O2—Cd1—O1—Cd1^iv	166.6 (4)
C2—C3—C4—C5	53.1 (11)	O5—Cd1—O1—Cd1^iv	83.2 (3)
C3—C4—C5—C6	−57.3 (11)	O3ⁱⁱ—Cd1—O1—Cd1^iv	−15.2 (3)
C4—C5—C6—C1	58.5 (10)	O1ⁱⁱⁱ—Cd1—O1—Cd1^iv	178.65 (11)
C11—C1—C6—C5	71.9 (8)	O6—Cd1—O1—Cd1^iv	−104.7 (3)
C2—C1—C6—C5	−54.0 (9)	O4ⁱⁱ—Cd1—O1—Cd1^iv	−42.3 (4)
C6—C1—C11—O2	−123.1 (7)	C21ⁱⁱ—Cd1—O1—Cd1^iv	−27.5 (4)
C2—C1—C11—O2	1.5 (10)	O1—C11—O2—Cd1	−4.1 (8)
C6—C1—C11—O1	59.1 (9)	C1—C11—O2—Cd1	178.1 (5)
C2—C1—C11—O1	−176.2 (6)	O5—Cd1—O2—C11	99.8 (5)
C3—C2—C21—O4	−12.9 (10)	O3ⁱⁱ—Cd1—O2—C11	−0.5 (6)
C1—C2—C21—O4	−142.0 (7)	O1ⁱⁱⁱ—Cd1—O2—C11	−169.1 (5)
C3—C2—C21—O3	169.7 (7)	O6—Cd1—O2—C11	−80.4 (5)
C1—C2—C21—O3	40.5 (9)	O4ⁱⁱ—Cd1—O2—C11	−113.9 (6)
O2—C11—O1—Cd1^iv	−162.3 (6)	O1—Cd1—O2—C11	2.1 (4)
C1—C11—O1—Cd1^iv	15.5 (12)	C21ⁱⁱ—Cd1—O2—C11	−36.3 (9)
O2—C11—O1—Cd1	3.5 (7)	O4—C21—O3—Cd1ⁱ	4.1 (7)
C1—C11—O1—Cd1	−178.8 (6)	C2—C21—O3—Cd1ⁱ	−178.4 (6)
O2—Cd1—O1—C11	−2.1 (4)	O3—C21—O4—Cd1ⁱ	−4.0 (7)
O5—Cd1—O1—C11	−85.5 (4)	C2—C21—O4—Cd1ⁱ	178.6 (6)

Symmetry codes: (i) x−1, −y+3/2, z−1/2; (ii) x+1, −y+3/2, z+1/2; (iii) x, −y+3/2, z−1/2; (iv) x, −y+3/2, z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H11···O6ⁱ	0.85	2.01	2.828 (8)	164
O5—H12···O4^iv	0.85	1.89	2.725 (8)	169
O6—H13···O3^v	0.85	1.85	2.694 (8)	175
O6—H14···O2ⁱⁱ	0.84	2.49	3.147 (8)	136
O6—H14···O4ⁱⁱ	0.84	2.57	3.016 (8)	115
C3—H3···O2	0.97	2.59	3.120 (10)	115
C6—H9···O4^vi	0.97	2.30	3.257 (10)	169

Symmetry codes: (i) x−1, −y+3/2, z−1/2; (ii) x+1, −y+3/2, z+1/2; (iv) x, −y+3/2, z+1/2; (v) x+1, y, z; (vi) x+1, y, z+1.

Experimental details

Crystal data
Chemical formula	[Cd(C₈H₁₀O₄)(H₂O)₂]
M_r	318.59
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	6.0585 (9), 23.544 (3), 8.3308 (9)
β (°)	118.787 (8)
V (Å³)	1041.5 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.10
Crystal size (mm)	0.20 × 0.20 × 0.18

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.678, 0.703
No. of measured, independent and observed [I > 2σ(I)] reflections	5908, 2250, 2214
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.062, 0.132, 1.51
No. of reflections	2250
No. of parameters	136
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.31, −2.11

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2000), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H11···O6ⁱ	0.85	2.01	2.828 (8)	163.6
O5—H12···O4ⁱⁱ	0.85	1.89	2.725 (8)	169.4
O6—H13···O3ⁱⁱⁱ	0.85	1.85	2.694 (8)	174.5
O6—H14···O2^iv	0.84	2.49	3.147 (8)	136.0
O6—H14···O4^iv	0.84	2.57	3.016 (8)	114.6
C3—H3···O2	0.97	2.59	3.120 (10)	115.0
C6—H9···O4^v	0.97	2.30	3.257 (10)	169.00

Symmetry codes: (i) x−1, −y+3/2, z−1/2; (ii) x, −y+3/2, z+1/2; (iii) x+1, y, z; (iv) x+1, −y+3/2, z+1/2; (v) x+1, y, z+1.

Acknowledgements

The authors gratefully acknowledge the Natural Science Foundation of Jiangsu Province of China (BK2008195) for financial support of this work.

References

Brandenburg, K. (2000). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, wisconsin, USA. Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Thirumurugan, A., Avinash, M. B. & Rao, C. N. R. (2006). Dalton Trans. pp. 221–228. Web of Science CSD CrossRef Google Scholar