Aqua­bis(dichloro­acetato-κO)(1,10-phenanthroline-κ2N,N′)copper(II)

Liu, Y.; Ning, J.; Sun, J.; Zhang, C.

doi:10.1107/S1600536808042578

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 1| January 2009| Page m113

doi:10.1107/S1600536808042578

Open

access

Aquabis(dichloroacetato-κO)(1,10-phenanthroline-κ²N,N′)copper(II)

Yaru Liu,^a Jianzhong Ning,^b Junshan Sun ^c ^* and Chuan Zhang ^c

^aSchool of Science, North University of China, Taiyuan 030051, People's Republic of China, ^bCollege of Chemistry and Food, Zhongzhou University, Zhengzhou 450044, People's Republic of China, and ^cDepartment of Materials Science and Chemical Engineering, Taishan University, 271021 Taian, Shandong, People's Republic of China
^*Correspondence e-mail: xiangyz_2008@163.com

(Received 29 November 2008; accepted 15 December 2008; online 20 December 2008)

In the title complex, [Cu(C₂HCl₂O₂)₂(C₁₂H₈N₂)(H₂O)], the Cu^II ion has a distorted square-pyramidal coordination geometry. The equatorial positions are occupied by two N atoms from a 1,10-phenanthroline ligand [Cu—N = 1.994 (3) and 2.027 (3) Å] and two O atoms from dichloroacetate ligands and a water molecule [Cu—O = 1.971 (2) and 1.939 (2) Å]. One O atom from another dichloroacetate ligand occupies the apical positon [Cu—O = 2.152 (3) Å]. Intermolecular O—H⋯O hydrogen bonds link the molecules into centrosymmetric dimers. The crystal packing also exhibits weak intermolecular C—H⋯O hydrogen bonds, π–π interactions [centroid–centroid distance = 3.734 (2) Å] and short intermolecular Cl⋯Cl contacts [3.306 (2) and 3.278 (2) Å].

Related literature

For applications of dichloroacetic acid derivatives, see: Múdra et al. (2003 ); Lin et al. (2001 ); Zhu & Xiao (2006 ).

Experimental

Crystal data

[Cu(C₂HCl₂O₂)₂(C₁₂H₈N₂)(H₂O)]
M_r = 517.62
Triclinic, $[P \overline 1]$
a = 8.2701 (8) Å
b = 10.8883 (11) Å
c = 12.0125 (12) Å
α = 67.4390 (10)°
β = 77.585 (2)°
γ = 73.776 (2)°
V = 952.02 (16) Å³
Z = 2
Mo Kα radiation
μ = 1.74 mm⁻¹
T = 273 (2) K
0.32 × 0.25 × 0.21 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.606, T_max = 0.711
5043 measured reflections
3346 independent reflections
2539 reflections with I > 2σ(I)
R_int = 0.064

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.106
S = 1.01
3346 reflections
261 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.63 e Å⁻³
Δρ_min = −0.51 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16⋯O2ⁱ	0.98	2.24	3.118 (5)	149
O5—H5B⋯O2ⁱⁱ	0.85 (2)	1.81 (2)	2.654 (3)	174 (3)
O5—H5A⋯O4	0.85 (2)	1.86 (2)	2.673 (4)	159 (3)
Symmetry codes: (i) x-1, y, z; (ii) -x+1, -y+1, -z+1.

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; 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/S1600536808042578/cv2493sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808042578/cv2493Isup2.hkl

checkCIF report

Comment top

Dichloroacetic acid and its derivatives are biologically active compounds which have been widely studied because of their fascinating topologies and potential applications as functional materials (Múdra et al., 2003; Lin et al., 2001; Zhu et al., 2006;). In our study of this field, we selected 1,10-phenanthroline as the co-ligand to continue our exploration to the Cu complexes with the dichloroacetic acid ligand. Herein we report the structure of the title complex (I).

In (I) (Fig. 1), the Cu ion has a distorted square-pyramidal coordination. Two N atoms from 1,10-phenanthroline ligand and two oxygen atoms from a dichloroacetic acid ligand form a basal plane, and an aqua atom occupy the axial apical position. Intermolecular O—H···O hydrogen bonds (Table 2) link the molecules into centrosymmetric dimers. The crystal packing exhibits also weak intermolecular C—H···O hydrogen bonds, π–π interactions and short intermolecular Cl···Cl contacts (Table 1).

Related literature top

For applications of dichloroacetic acid derivatives, see: Múdra et al. (2003); Lin et al. (2001); Zhu et al. (2006).

Experimental top

A mixture of Cu(CH3COO)2*3H2O(204 mg, 1 mmol) and 1,10-phenanthroline (185 mg, 1 mmol) in methanol(30 ml) was placed in a Teflon-lined stainless steel Parr bomb that was heated at 403 K for 48 h. The bomb was then cooled down to the room temperature, the solution was filtered. The solvent was removed from the filtrate under vacuum, and the solid residue was recrystallized from diethyl ether; blue crystals suitable for X-Ray diffraction study were obtained. Yield, 0.760 g, 83%. m.p. 573 K. Analysis, calculated for C₁₆H₁₂Cl₄CuN₂O₅: C 46.73, H 2.94, N 6.81; found: C 46.95, H 2.56, N 7.07%. The elemental analyses were performed with a Perkine Elemer PE2400II instrument.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SMART (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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. The structure of the title complex, showing 30% probability displacement ellipsoids and the atom-numbering scheme. The H atoms are omitted.

Aquabis(dichloroacetato-κO)(1,10-phenanthroline- κ²N,N')copper(II) top

Crystal data top

[Cu(C₂HCl₂O₂)₂(C₁₂H₈N₂)(H₂O)]	Z = 2
M_r = 517.62	F(000) = 518
Triclinic, P1	D_x = 1.806 Mg m⁻³
a = 8.2701 (8) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.8883 (11) Å	Cell parameters from 1923 reflections
c = 12.0125 (12) Å	θ = 2.3–27.1°
α = 67.439 (1)°	µ = 1.74 mm⁻¹
β = 77.585 (2)°	T = 273 K
γ = 73.776 (2)°	Block, colorless
V = 952.02 (16) Å³	0.32 × 0.25 × 0.21 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3346 independent reflections
Radiation source: fine-focus sealed tube	2539 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.064
ϕ and ω scans	θ_max = 25.1°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→8
T_min = 0.606, T_max = 0.711	k = −12→12
5043 measured reflections	l = −14→14

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.106	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.046P)²] where P = (F_o² + 2F_c²)/3
3346 reflections	(Δ/σ)_max < 0.001
261 parameters	Δρ_max = 0.63 e Å⁻³
3 restraints	Δρ_min = −0.51 e Å⁻³

Crystal data top

[Cu(C₂HCl₂O₂)₂(C₁₂H₈N₂)(H₂O)]	γ = 73.776 (2)°
M_r = 517.62	V = 952.02 (16) Å³
Triclinic, P1	Z = 2
a = 8.2701 (8) Å	Mo Kα radiation
b = 10.8883 (11) Å	µ = 1.74 mm⁻¹
c = 12.0125 (12) Å	T = 273 K
α = 67.439 (1)°	0.32 × 0.25 × 0.21 mm
β = 77.585 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3346 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2539 reflections with I > 2σ(I)
T_min = 0.606, T_max = 0.711	R_int = 0.064
5043 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	3 restraints
wR(F²) = 0.106	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.63 e Å⁻³
3346 reflections	Δρ_min = −0.51 e Å⁻³
261 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
Cu1	0.23680 (6)	0.74569 (4)	0.41387 (4)	0.03375 (16)
Cl4	0.12884 (15)	0.83880 (10)	0.01776 (9)	0.0498 (3)
Cl3	0.18005 (19)	0.55281 (11)	0.05837 (10)	0.0653 (4)
Cl1	0.66991 (17)	0.90846 (12)	0.08639 (11)	0.0717 (4)
Cl2	0.5908 (2)	0.69108 (14)	0.04161 (11)	0.0831 (5)
O3	0.1567 (3)	0.7463 (2)	0.2733 (2)	0.0399 (6)
C5	0.2814 (4)	0.9060 (3)	0.5379 (3)	0.0310 (8)
O5	0.1749 (4)	0.5698 (3)	0.5130 (2)	0.0471 (7)
N2	0.1747 (4)	0.9522 (3)	0.3541 (2)	0.0324 (7)
N1	0.3082 (4)	0.7741 (3)	0.5489 (3)	0.0343 (7)
C9	0.0716 (5)	1.1808 (4)	0.2276 (3)	0.0447 (10)
H9	0.0263	1.2392	0.1564	0.054*
O2	0.7530 (4)	0.6097 (3)	0.2708 (2)	0.0586 (8)
C13	0.6067 (5)	0.6806 (4)	0.2683 (3)	0.0344 (8)
C16	0.0957 (5)	0.6794 (3)	0.1249 (3)	0.0340 (8)
H16	−0.0272	0.6861	0.1432	0.041*
C11	0.2127 (6)	1.1856 (4)	0.4993 (4)	0.0471 (10)
H11	0.1873	1.2779	0.4887	0.056*
C15	0.1639 (5)	0.6447 (3)	0.2447 (3)	0.0341 (8)
O4	0.2088 (4)	0.5243 (3)	0.3049 (2)	0.0609 (9)
C14	0.5542 (5)	0.7783 (4)	0.1437 (3)	0.0357 (9)
H14	0.4330	0.8198	0.1536	0.043*
C1	0.3872 (5)	0.6806 (4)	0.6436 (3)	0.0447 (10)
H1	0.4132	0.5893	0.6509	0.054*
C12	0.2859 (6)	1.0935 (4)	0.5985 (4)	0.0510 (11)
H12	0.3130	1.1242	0.6531	0.061*
C8	0.1025 (5)	1.2327 (4)	0.3051 (3)	0.0421 (10)
H8	0.0766	1.3264	0.2879	0.051*
C10	0.1075 (5)	1.0398 (4)	0.2542 (3)	0.0398 (9)
H10	0.0836	1.0063	0.2004	0.048*
C6	0.2062 (5)	1.0040 (3)	0.4314 (3)	0.0306 (8)
C7	0.1742 (5)	1.1436 (4)	0.4118 (3)	0.0368 (9)
C4	0.3223 (5)	0.9501 (4)	0.6208 (3)	0.0390 (9)
C2	0.4306 (6)	0.7160 (4)	0.7297 (4)	0.0506 (11)
H2	0.4810	0.6482	0.7955	0.061*
O1	0.5012 (4)	0.6801 (3)	0.3559 (2)	0.0634 (9)
C3	0.4009 (6)	0.8478 (4)	0.7199 (3)	0.0477 (10)
H3	0.4321	0.8710	0.7779	0.057*
H5A	0.192 (6)	0.535 (3)	0.458 (2)	0.065 (16)*
H5B	0.194 (6)	0.509 (3)	0.5816 (15)	0.068 (15)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0471 (3)	0.0207 (2)	0.0318 (3)	−0.00140 (19)	−0.0107 (2)	−0.00826 (19)
Cl4	0.0728 (8)	0.0307 (5)	0.0416 (6)	−0.0135 (5)	−0.0179 (5)	−0.0005 (4)
Cl3	0.1158 (11)	0.0350 (6)	0.0486 (6)	−0.0027 (6)	−0.0209 (6)	−0.0222 (5)
Cl1	0.0801 (9)	0.0472 (7)	0.0746 (8)	−0.0293 (6)	−0.0338 (7)	0.0168 (6)
Cl2	0.1151 (12)	0.0745 (9)	0.0677 (8)	0.0119 (8)	−0.0340 (8)	−0.0440 (7)
O3	0.0622 (18)	0.0227 (13)	0.0366 (14)	−0.0029 (12)	−0.0151 (13)	−0.0119 (11)
C5	0.034 (2)	0.0258 (19)	0.0303 (18)	−0.0034 (15)	−0.0046 (16)	−0.0087 (15)
O5	0.073 (2)	0.0312 (15)	0.0346 (16)	−0.0132 (15)	−0.0142 (15)	−0.0038 (14)
N2	0.0419 (19)	0.0222 (16)	0.0315 (16)	−0.0044 (13)	−0.0051 (14)	−0.0090 (13)
N1	0.0420 (18)	0.0271 (17)	0.0326 (16)	−0.0042 (14)	−0.0059 (14)	−0.0104 (13)
C9	0.058 (3)	0.026 (2)	0.039 (2)	−0.0008 (18)	−0.014 (2)	−0.0011 (17)
O2	0.0396 (17)	0.0558 (19)	0.0453 (16)	0.0073 (15)	−0.0018 (14)	0.0063 (14)
C13	0.037 (2)	0.029 (2)	0.037 (2)	−0.0090 (17)	−0.0027 (18)	−0.0108 (17)
C16	0.041 (2)	0.0239 (19)	0.0350 (19)	−0.0038 (16)	−0.0062 (17)	−0.0094 (16)
C11	0.066 (3)	0.029 (2)	0.052 (2)	−0.010 (2)	−0.010 (2)	−0.018 (2)
C15	0.041 (2)	0.024 (2)	0.034 (2)	−0.0025 (16)	−0.0069 (17)	−0.0084 (16)
O4	0.113 (3)	0.0235 (15)	0.0449 (16)	0.0005 (16)	−0.0331 (17)	−0.0086 (13)
C14	0.032 (2)	0.030 (2)	0.039 (2)	−0.0029 (16)	−0.0048 (17)	−0.0088 (16)
C1	0.060 (3)	0.024 (2)	0.044 (2)	−0.0006 (19)	−0.018 (2)	−0.0048 (17)
C12	0.072 (3)	0.043 (3)	0.051 (3)	−0.018 (2)	−0.008 (2)	−0.026 (2)
C8	0.051 (3)	0.0200 (19)	0.047 (2)	−0.0035 (17)	−0.007 (2)	−0.0049 (17)
C10	0.051 (2)	0.030 (2)	0.035 (2)	−0.0034 (18)	−0.0145 (18)	−0.0065 (17)
C6	0.034 (2)	0.0242 (19)	0.0298 (18)	−0.0039 (15)	0.0009 (15)	−0.0097 (15)
C7	0.040 (2)	0.0229 (19)	0.042 (2)	−0.0055 (16)	−0.0010 (18)	−0.0088 (17)
C4	0.044 (2)	0.039 (2)	0.036 (2)	−0.0094 (18)	−0.0024 (18)	−0.0149 (18)
C2	0.063 (3)	0.043 (3)	0.040 (2)	−0.005 (2)	−0.020 (2)	−0.006 (2)
O1	0.0491 (19)	0.083 (2)	0.0386 (16)	0.0057 (16)	−0.0020 (15)	−0.0158 (16)
C3	0.057 (3)	0.052 (3)	0.038 (2)	−0.010 (2)	−0.014 (2)	−0.016 (2)

Geometric parameters (Å, º) top

Cu1—O3	1.939 (2)	C13—O1	1.213 (4)
Cu1—O5	1.971 (2)	C13—C14	1.536 (5)
Cu1—N1	1.994 (3)	C16—C15	1.531 (5)
Cu1—N2	2.027 (3)	C16—H16	0.9800
Cu1—O1	2.152 (3)	C11—C12	1.359 (6)
Cl4—C16	1.774 (3)	C11—C7	1.417 (5)
Cl3—C16	1.759 (4)	C11—H11	0.9300
Cl1—C14	1.767 (4)	C15—O4	1.223 (4)
Cl2—C14	1.753 (4)	C14—H14	0.9800
O3—C15	1.261 (4)	C1—C2	1.374 (5)
C5—N1	1.348 (4)	C1—H1	0.9300
C5—C4	1.394 (5)	C12—C4	1.432 (5)
C5—C6	1.444 (5)	C12—H12	0.9300
O5—H5A	0.85 (3)	C8—C7	1.410 (5)
O5—H5B	0.85 (3)	C8—H8	0.9300
N2—C10	1.331 (4)	C10—H10	0.9300
N2—C6	1.355 (4)	C6—C7	1.401 (5)
N1—C1	1.348 (4)	C4—C3	1.411 (5)
C9—C8	1.355 (5)	C2—C3	1.349 (5)
C9—C10	1.399 (5)	C2—H2	0.9300
C9—H9	0.9300	C3—H3	0.9300
O2—C13	1.240 (5)

Cl1···Cl4ⁱ	3.306 (2)	Cg1···Cg2ⁱⁱⁱ	3.734 (2)
Cl2···Cl3ⁱⁱ	3.278 (2)

O3—Cu1—O5	91.06 (10)	O4—C15—O3	127.3 (3)
O3—Cu1—N1	171.76 (11)	O4—C15—C16	117.8 (3)
O5—Cu1—N1	95.86 (11)	O3—C15—C16	114.7 (3)
O3—Cu1—N2	90.28 (11)	C13—C14—Cl2	110.9 (3)
O5—Cu1—N2	149.53 (12)	C13—C14—Cl1	109.3 (2)
N1—Cu1—N2	81.49 (11)	Cl2—C14—Cl1	110.0 (2)
O3—Cu1—O1	95.15 (11)	C13—C14—H14	108.9
O5—Cu1—O1	101.24 (12)	Cl2—C14—H14	108.9
N1—Cu1—O1	87.88 (12)	Cl1—C14—H14	108.9
N2—Cu1—O1	108.94 (12)	N1—C1—C2	122.1 (4)
C15—O3—Cu1	127.3 (2)	N1—C1—H1	118.9
N1—C5—C4	124.2 (3)	C2—C1—H1	119.0
N1—C5—C6	115.7 (3)	C11—C12—C4	121.4 (4)
C4—C5—C6	120.1 (3)	C11—C12—H12	119.3
Cu1—O5—H5A	99 (2)	C4—C12—H12	119.3
Cu1—O5—H5B	137 (3)	C9—C8—C7	119.6 (3)
H5A—O5—H5B	111 (3)	C9—C8—H8	120.2
C10—N2—C6	117.7 (3)	C7—C8—H8	120.2
C10—N2—Cu1	129.8 (3)	N2—C10—C9	121.9 (4)
C6—N2—Cu1	112.5 (2)	N2—C10—H10	119.0
C1—N1—C5	117.1 (3)	C9—C10—H10	119.1
C1—N1—Cu1	128.6 (3)	N2—C6—C7	124.1 (3)
C5—N1—Cu1	114.1 (2)	N2—C6—C5	116.1 (3)
C8—C9—C10	120.4 (4)	C7—C6—C5	119.8 (3)
C8—C9—H9	119.8	C6—C7—C8	116.3 (3)
C10—C9—H9	119.8	C6—C7—C11	118.9 (3)
O1—C13—O2	125.7 (4)	C8—C7—C11	124.7 (3)
O1—C13—C14	117.0 (3)	C5—C4—C3	116.3 (3)
O2—C13—C14	117.3 (3)	C5—C4—C12	118.5 (3)
C15—C16—Cl3	113.0 (3)	C3—C4—C12	125.2 (3)
C15—C16—Cl4	112.4 (2)	C3—C2—C1	120.8 (3)
Cl3—C16—Cl4	109.30 (19)	C3—C2—H2	119.6
C15—C16—H16	107.3	C1—C2—H2	119.6
Cl3—C16—H16	107.3	C13—O1—Cu1	144.6 (3)
Cl4—C16—H16	107.3	C2—C3—C4	119.4 (3)
C12—C11—C7	121.2 (4)	C2—C3—H3	120.3
C12—C11—H11	119.4	C4—C3—H3	120.3
C7—C11—H11	119.4

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16···O2^iv	0.98	2.24	3.118 (5)	149
O5—H5B···O2^v	0.85 (2)	1.81 (2)	2.654 (3)	174 (3)
O5—H5A···O4	0.85 (2)	1.86 (2)	2.673 (4)	159 (3)

Symmetry codes: (iv) x−1, y, z; (v) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[Cu(C₂HCl₂O₂)₂(C₁₂H₈N₂)(H₂O)]
M_r	517.62
Crystal system, space group	Triclinic, P1
Temperature (K)	273
a, b, c (Å)	8.2701 (8), 10.8883 (11), 12.0125 (12)
α, β, γ (°)	67.439 (1), 77.585 (2), 73.776 (2)
V (Å³)	952.02 (16)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.74
Crystal size (mm)	0.32 × 0.25 × 0.21

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.606, 0.711
No. of measured, independent and observed [I > 2σ(I)] reflections	5043, 3346, 2539
R_int	0.064
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.106, 1.01
No. of reflections	3346
No. of parameters	261
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.63, −0.51

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), 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
C16—H16···O2ⁱ	0.98	2.24	3.118 (5)	148.6
O5—H5B···O2ⁱⁱ	0.85 (2)	1.81 (2)	2.654 (3)	174 (3)
O5—H5A···O4	0.85 (2)	1.86 (2)	2.673 (4)	159 (3)

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

Acknowledgements

The authors thank the Postgraduate Foundation of Taishan University for financial support (grant No. Y07–2–15).

References

Lin, M. M., Wei, H. H. & Lee, G. H. (2001). Polyhedron, 20, 3057–3063. Web of Science CSD CrossRef CAS Google Scholar
Múdra, M., Moncol', J., Švorec, J., Melník, M., Lönnecke, P., Glowiak, T. & Kirmse, R. (2003). Inorg. Chem. Commun. 6, 1259–1265. 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
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar
Zhu, L.-G. & Xiao, H.-P. (2006). Acta Cryst. E62, m2061–m2063. Web of Science CSD CrossRef IUCr Journals Google Scholar