Hexaaqua­nickel(II) bis­[4-(2-hydroxy­benzyl­ideneamino)benzene­sulfonate]

Tai, X.-S.; Xu, J.; Feng, Y.-M.; Liang, Z.-P.

doi:10.1107/S1600536808015262

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 7| July 2008| Page m893

doi:10.1107/S1600536808015262

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Hexaaquanickel(II) bis[4-(2-hydroxybenzylideneamino)benzenesulfonate]

Xi-Shi Tai,^a ^* Jun Xu,^b Yi-Min Feng ^a and Zu-Pei Liang ^a

^aDepartment of Chemistry and Chemical Engineering, Weifang University, Weifang 261061, People's Republic of China, and ^bWeifang Institute of Supervision and Inspection, on Product Quality, Weifang 261031, People's Republic of China
^*Correspondence e-mail: taixishi@lzu.edu.cn

(Received 16 May 2008; accepted 21 May 2008; online 7 June 2008)

In the title compound, [Ni(H₂O)₆](C_(C₁₃H₁₀NO₄S)₂, the nickel(II) atom, lying on a center of symmetry, is six-coordinated by six aqua O-atom donors. The dihedral angle between the two benzene rings is 33.1 (3)°. The crystal structure is stabilized by aqua–anion O—H⋯O hydrogen bonds. Intramolecular O—H⋯N and C—H⋯O hydrogen-bonding interactions occur in the anion.

Related literature

For related literature, see: Tai & Feng (2008 ); Tai et al. (2003 , 2008 ); Tai, Yin & Feng (2007 ); Tai, Yin & Hao (2007 ); Tai, Yin, Feng & Kong (2007 ); Wang et al. (2007 ).

Experimental

Crystal data

[Ni(H₂O)₆](C₁₃H₁₀NO₄S)₂
M_r = 719.37
Monoclinic, P 2₁ /c
a = 6.3047 (6) Å
b = 35.193 (3) Å
c = 9.3536 (10) Å
β = 131.822 (2)°
V = 1546.6 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.83 mm⁻¹
T = 298 (2) K
0.43 × 0.38 × 0.25 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.716, T_max = 0.819
7465 measured reflections
2661 independent reflections
2428 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.067
wR(F²) = 0.137
S = 1.28
2661 reflections
205 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −1.00 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4⋯N1	0.82	1.86	2.595 (9)	148
O5—H5A⋯O1ⁱ	0.85	1.96	2.737 (6)	151
O5—H5B⋯O2ⁱⁱ	0.85	1.98	2.751 (6)	150
O6—H6A⋯O3ⁱ	0.85	1.95	2.764 (7)	161
O6—H6B⋯O1ⁱⁱⁱ	0.85	1.97	2.768 (8)	156
O7—H7A⋯O2	0.85	2.00	2.757 (8)	148
O7—H7B⋯O3ⁱⁱ	0.85	2.00	2.769 (7)	150
C2—H2⋯O3	0.93	2.56	2.917 (7)	104
Symmetry codes: (i) x, y, z+1; (ii) x-1, y, z; (iii) x+1, y, z+1.

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); 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 global, I. DOI: 10.1107/S1600536808015262/at2568sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808015262/at2568Isup2.hkl

checkCIF report

Comment top

As part of our ongoing studies of the coordination chemistry of Schiffbase ligands (Tai et al., 2003; (Tai, Yin & Feng, 2007; Tai, Yin, Feng & Kong, 2007; Tai, Yin & Hao, 2007; Wang et al., 2007; Tai et al., 2008; Tai et al., 2008), we now report the synthesis and structure of the title compound, (I), (Fig. 1).

In the molecule of (I), the nickel (II) center is six-coordinate with six O donor of H₂O. The C7—N1 [1.288 (8) Å] is close to double-bond. Otherwise, the geometrical parameters for (I) are normal. The dihedral angle between the two benzene rings is 33.1°. The packing is stabilized by O_water—H···O_anion hydrogen bonds. The intramolecular O—H···N and C—H···O hydrogen bonding interactions occur in the anion. (Table 1).

Related literature top

For related literature, see: Tai & Feng (2008); Tai et al. (2003, 2008); Tai, Yin & Feng (2007); Tai, Yin & Hao (2007); Tai, Yin et al. (2007); Wang et al. (2007).

Experimental top

1 mmol of Ni(CH₃COO)₂.4H₂O was added to a solution of salicylaldehyde-4-aminobenzene sulfonic acid (1 mmol) in 10 ml of 95% ethanol. The mixture was stirred for 2 h at refluxing temperature. Evaporating some ethanol, clear blocks of (I) were obtained after one weeks.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 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. The molecular structure of (I) showing 30% displacement ellipsoids.

Hexaaquanickel(II) bis[4-(2-hydroxybenzylideneamino)benzenesulfonate] top

Crystal data top

[Ni(H₂O)₆](C₁₃H₁₀NO₄S)₂	F(000) = 748
M_r = 719.37	D_x = 1.545 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4537 reflections
a = 6.3047 (6) Å	θ = 2.9–27.7°
b = 35.193 (3) Å	µ = 0.83 mm⁻¹
c = 9.3536 (10) Å	T = 298 K
β = 131.822 (2)°	Block, colourless
V = 1546.6 (3) Å³	0.43 × 0.38 × 0.25 mm
Z = 2

Data collection top

Bruker SMART CCD area-detector diffractometer	2661 independent reflections
Radiation source: fine-focus sealed tube	2428 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −7→5
T_min = 0.716, T_max = 0.819	k = −41→40
7465 measured reflections	l = −9→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)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.137	H-atom parameters constrained
S = 1.28	w = 1/[σ²(F_o²) + (0.0161P)² + 4.8144P] where P = (F_o² + 2F_c²)/3
2661 reflections	(Δ/σ)_max < 0.001
205 parameters	Δρ_max = 0.32 e Å⁻³
0 restraints	Δρ_min = −1.00 e Å⁻³

Crystal data top

[Ni(H₂O)₆](C₁₃H₁₀NO₄S)₂	V = 1546.6 (3) Å³
M_r = 719.37	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 6.3047 (6) Å	µ = 0.83 mm⁻¹
b = 35.193 (3) Å	T = 298 K
c = 9.3536 (10) Å	0.43 × 0.38 × 0.25 mm
β = 131.822 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2661 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	2428 reflections with I > 2σ(I)
T_min = 0.716, T_max = 0.819	R_int = 0.032
7465 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.067	0 restraints
wR(F²) = 0.137	H-atom parameters constrained
S = 1.28	Δρ_max = 0.32 e Å⁻³
2661 reflections	Δρ_min = −1.00 e Å⁻³
205 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
Ni1	0.5000	1.0000	1.0000	0.0310 (2)
N1	0.4029 (11)	0.76969 (14)	0.4874 (8)	0.0565 (13)
O1	0.3354 (7)	0.95021 (11)	0.3248 (5)	0.0486 (10)
O2	0.6843 (8)	0.94957 (11)	0.6726 (5)	0.0462 (9)
O3	0.8302 (7)	0.93929 (10)	0.4933 (5)	0.0392 (8)
O4	0.0669 (10)	0.71618 (13)	0.4256 (8)	0.0767 (14)
H4	0.1257	0.7379	0.4400	0.115*
O5	0.2072 (7)	0.97532 (11)	0.9978 (5)	0.0474 (9)
H5A	0.2819	0.9621	1.0975	0.071*
H5B	0.0852	0.9623	0.8972	0.071*
O6	0.7945 (8)	0.96016 (12)	1.1929 (6)	0.0549 (11)
H6A	0.8124	0.9592	1.2913	0.082*
H6B	0.9559	0.9642	1.2273	0.082*
O7	0.3791 (8)	0.96590 (13)	0.7796 (6)	0.0600 (12)
H7A	0.4709	0.9703	0.7444	0.090*
H7B	0.2009	0.9665	0.6838	0.090*
S1	0.6046 (2)	0.93471 (4)	0.49681 (17)	0.0319 (3)
C1	0.5566 (9)	0.88532 (14)	0.4986 (7)	0.0313 (10)
C2	0.6556 (12)	0.86005 (16)	0.4406 (8)	0.0451 (13)
H2	0.7524	0.8689	0.4039	0.054*
C3	0.6082 (14)	0.82145 (16)	0.4382 (9)	0.0529 (15)
H3	0.6758	0.8042	0.4012	0.063*
C4	0.4623 (12)	0.80853 (16)	0.4899 (9)	0.0483 (14)
C5	0.3614 (13)	0.83417 (16)	0.5454 (9)	0.0509 (15)
H5	0.2614	0.8253	0.5795	0.061*
C6	0.4079 (12)	0.87246 (15)	0.5503 (8)	0.0438 (13)
H6	0.3404	0.8896	0.5878	0.053*
C7	0.5721 (13)	0.74368 (17)	0.5168 (9)	0.0525 (15)
H7	0.7384	0.7507	0.5446	0.063*
C8	0.5084 (15)	0.70327 (16)	0.5074 (9)	0.0527 (14)
C9	0.2544 (14)	0.69149 (18)	0.4569 (9)	0.0589 (17)
C10	0.1982 (16)	0.65268 (18)	0.4407 (9)	0.0643 (18)
H10	0.0295	0.6445	0.4068	0.077*
C11	0.3845 (17)	0.6265 (2)	0.4733 (9)	0.068 (2)
H11	0.3396	0.6008	0.4588	0.082*
C12	0.6424 (19)	0.6376 (2)	0.5281 (11)	0.077 (2)
H12	0.7726	0.6196	0.5549	0.092*
C13	0.7008 (15)	0.67614 (18)	0.5417 (9)	0.0610 (17)
H13	0.8689	0.6840	0.5739	0.073*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0214 (4)	0.0436 (5)	0.0287 (4)	−0.0007 (4)	0.0170 (4)	−0.0012 (4)
N1	0.060 (3)	0.044 (3)	0.061 (3)	−0.010 (2)	0.038 (3)	−0.004 (2)
O1	0.0284 (19)	0.064 (2)	0.048 (2)	0.0099 (18)	0.0234 (19)	0.0211 (19)
O2	0.042 (2)	0.056 (2)	0.051 (2)	−0.0096 (18)	0.035 (2)	−0.0105 (18)
O3	0.0269 (17)	0.055 (2)	0.041 (2)	−0.0029 (16)	0.0250 (16)	0.0003 (17)
O4	0.056 (3)	0.059 (3)	0.094 (4)	−0.008 (2)	0.042 (3)	0.002 (3)
O5	0.0309 (19)	0.074 (3)	0.035 (2)	−0.0104 (19)	0.0206 (17)	−0.0005 (19)
O6	0.038 (2)	0.082 (3)	0.055 (3)	0.018 (2)	0.035 (2)	0.025 (2)
O7	0.036 (2)	0.100 (3)	0.053 (3)	−0.023 (2)	0.033 (2)	−0.033 (2)
S1	0.0229 (6)	0.0420 (7)	0.0311 (6)	−0.0014 (5)	0.0181 (5)	0.0003 (5)
C1	0.021 (2)	0.041 (3)	0.027 (2)	−0.004 (2)	0.014 (2)	−0.002 (2)
C2	0.053 (3)	0.049 (3)	0.047 (3)	−0.003 (3)	0.039 (3)	−0.004 (3)
C3	0.066 (4)	0.046 (3)	0.054 (4)	−0.006 (3)	0.043 (3)	−0.012 (3)
C4	0.041 (3)	0.046 (3)	0.049 (3)	−0.007 (3)	0.026 (3)	0.001 (3)
C5	0.054 (4)	0.046 (3)	0.068 (4)	−0.004 (3)	0.047 (4)	0.001 (3)
C6	0.053 (3)	0.044 (3)	0.053 (3)	−0.004 (3)	0.043 (3)	0.001 (3)
C7	0.050 (4)	0.056 (4)	0.048 (4)	−0.014 (3)	0.031 (3)	−0.009 (3)
C8	0.059 (4)	0.045 (3)	0.047 (3)	−0.008 (3)	0.032 (3)	−0.008 (3)
C9	0.050 (4)	0.049 (4)	0.048 (4)	−0.003 (3)	0.021 (3)	0.002 (3)
C10	0.065 (4)	0.049 (4)	0.055 (4)	−0.014 (3)	0.030 (4)	−0.002 (3)
C11	0.082 (5)	0.050 (4)	0.051 (4)	−0.013 (4)	0.035 (4)	0.000 (3)
C12	0.098 (6)	0.049 (4)	0.079 (5)	0.000 (4)	0.057 (5)	0.002 (4)
C13	0.068 (4)	0.052 (4)	0.063 (4)	−0.007 (3)	0.044 (4)	−0.007 (3)

Geometric parameters (Å, º) top

Ni1—O5ⁱ	2.028 (3)	C1—C2	1.388 (7)
Ni1—O5	2.028 (3)	C2—C3	1.388 (8)
Ni1—O7ⁱ	2.043 (4)	C2—H2	0.9300
Ni1—O7	2.043 (4)	C3—C4	1.371 (8)
Ni1—O6	2.049 (4)	C3—H3	0.9300
Ni1—O6ⁱ	2.049 (4)	C4—C5	1.389 (8)
N1—C7	1.288 (8)	C5—C6	1.373 (8)
N1—C4	1.414 (7)	C5—H5	0.9300
O1—S1	1.458 (4)	C6—H6	0.9300
O2—S1	1.459 (4)	C7—C8	1.465 (8)
O3—S1	1.454 (3)	C7—H7	0.9300
O4—C9	1.333 (8)	C8—C9	1.397 (9)
O4—H4	0.8209	C8—C13	1.402 (9)
O5—H5A	0.8494	C9—C10	1.394 (8)
O5—H5B	0.8492	C10—C11	1.357 (10)
O6—H6A	0.8500	C10—H10	0.9300
O6—H6B	0.8498	C11—C12	1.396 (10)
O7—H7A	0.8497	C11—H11	0.9300
O7—H7B	0.8504	C12—C13	1.387 (9)
S1—C1	1.767 (5)	C12—H12	0.9300
C1—C6	1.387 (7)	C13—H13	0.9300

O5ⁱ—Ni1—O5	180.0 (2)	C3—C2—H2	120.5
O5ⁱ—Ni1—O7ⁱ	90.78 (15)	C1—C2—H2	120.5
O5—Ni1—O7ⁱ	89.22 (15)	C4—C3—C2	120.4 (5)
O5ⁱ—Ni1—O7	89.22 (15)	C4—C3—H3	119.8
O5—Ni1—O7	90.78 (15)	C2—C3—H3	119.8
O7ⁱ—Ni1—O7	180.000 (2)	C3—C4—C5	119.9 (5)
O5ⁱ—Ni1—O6	89.99 (15)	C3—C4—N1	123.2 (6)
O5—Ni1—O6	90.01 (15)	C5—C4—N1	116.9 (5)
O7ⁱ—Ni1—O6	90.23 (18)	C6—C5—C4	120.6 (5)
O7—Ni1—O6	89.77 (18)	C6—C5—H5	119.7
O5ⁱ—Ni1—O6ⁱ	90.01 (15)	C4—C5—H5	119.7
O5—Ni1—O6ⁱ	89.99 (15)	C5—C6—C1	119.1 (5)
O7ⁱ—Ni1—O6ⁱ	89.77 (18)	C5—C6—H6	120.4
O7—Ni1—O6ⁱ	90.23 (18)	C1—C6—H6	120.4
O6—Ni1—O6ⁱ	180.000 (3)	N1—C7—C8	121.5 (6)
C7—N1—C4	120.7 (5)	N1—C7—H7	119.3
C9—O4—H4	109.5	C8—C7—H7	119.3
Ni1—O5—H5A	112.9	C9—C8—C13	119.8 (6)
Ni1—O5—H5B	112.8	C9—C8—C7	121.0 (6)
H5A—O5—H5B	110.6	C13—C8—C7	119.1 (6)
Ni1—O6—H6A	111.7	O4—C9—C8	122.0 (6)
Ni1—O6—H6B	111.9	O4—C9—C10	119.4 (6)
H6A—O6—H6B	109.6	C8—C9—C10	118.6 (7)
Ni1—O7—H7A	113.0	C11—C10—C9	121.4 (7)
Ni1—O7—H7B	112.9	C11—C10—H10	119.3
H7A—O7—H7B	110.5	C9—C10—H10	119.3
O3—S1—O1	111.7 (2)	C10—C11—C12	120.9 (7)
O3—S1—O2	112.3 (2)	C10—C11—H11	119.5
O1—S1—O2	112.5 (2)	C12—C11—H11	119.5
O3—S1—C1	106.6 (2)	C13—C12—C11	118.7 (8)
O1—S1—C1	107.3 (2)	C13—C12—H12	120.6
O2—S1—C1	105.9 (2)	C11—C12—H12	120.6
C6—C1—C2	120.8 (5)	C12—C13—C8	120.5 (7)
C6—C1—S1	119.0 (4)	C12—C13—H13	119.7
C2—C1—S1	120.2 (4)	C8—C13—H13	119.7
C3—C2—C1	119.0 (5)

O3—S1—C1—C6	163.8 (4)	C2—C1—C6—C5	0.6 (8)
O1—S1—C1—C6	−76.3 (5)	S1—C1—C6—C5	177.7 (4)
O2—S1—C1—C6	44.1 (5)	C4—N1—C7—C8	−177.6 (5)
O3—S1—C1—C2	−19.0 (5)	N1—C7—C8—C9	3.2 (10)
O1—S1—C1—C2	100.8 (4)	N1—C7—C8—C13	−179.6 (6)
O2—S1—C1—C2	−138.8 (4)	C13—C8—C9—O4	179.1 (6)
C6—C1—C2—C3	−1.1 (8)	C7—C8—C9—O4	−3.8 (10)
S1—C1—C2—C3	−178.2 (4)	C13—C8—C9—C10	−0.4 (10)
C1—C2—C3—C4	0.8 (9)	C7—C8—C9—C10	176.8 (6)
C2—C3—C4—C5	−0.1 (10)	O4—C9—C10—C11	−179.3 (6)
C2—C3—C4—N1	178.9 (6)	C8—C9—C10—C11	0.2 (10)
C7—N1—C4—C3	29.9 (9)	C9—C10—C11—C12	1.3 (11)
C7—N1—C4—C5	−151.1 (6)	C10—C11—C12—C13	−2.4 (11)
C3—C4—C5—C6	−0.4 (10)	C11—C12—C13—C8	2.2 (10)
N1—C4—C5—C6	−179.5 (6)	C9—C8—C13—C12	−0.8 (10)
C4—C5—C6—C1	0.2 (9)	C7—C8—C13—C12	−178.0 (6)

Symmetry code: (i) −x+1, −y+2, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···N1	0.82	1.86	2.595 (9)	148
O5—H5A···O1ⁱⁱ	0.85	1.96	2.737 (6)	151
O5—H5B···O2ⁱⁱⁱ	0.85	1.98	2.751 (6)	150
O6—H6A···O3ⁱⁱ	0.85	1.95	2.764 (7)	161
O6—H6B···O1^iv	0.85	1.97	2.768 (8)	156
O7—H7A···O2	0.85	2.00	2.757 (8)	148
O7—H7B···O3ⁱⁱⁱ	0.85	2.00	2.769 (7)	150
C2—H2···O3	0.93	2.56	2.917 (7)	104

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

Experimental details

Crystal data
Chemical formula	[Ni(H₂O)₆](C₁₃H₁₀NO₄S)₂
M_r	719.37
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	6.3047 (6), 35.193 (3), 9.3536 (10)
β (°)	131.822 (2)
V (Å³)	1546.6 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.83
Crystal size (mm)	0.43 × 0.38 × 0.25

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.716, 0.819
No. of measured, independent and observed [I > 2σ(I)] reflections	7465, 2661, 2428
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.067, 0.137, 1.28
No. of reflections	2661
No. of parameters	205
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −1.00

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 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
O4—H4···N1	0.82	1.86	2.595 (9)	148
O5—H5A···O1ⁱ	0.85	1.96	2.737 (6)	151
O5—H5B···O2ⁱⁱ	0.85	1.98	2.751 (6)	150
O6—H6A···O3ⁱ	0.85	1.95	2.764 (7)	161
O6—H6B···O1ⁱⁱⁱ	0.85	1.97	2.768 (8)	156
O7—H7A···O2	0.85	2.00	2.757 (8)	148
O7—H7B···O3ⁱⁱ	0.85	2.00	2.769 (7)	150
C2—H2···O3	0.93	2.56	2.917 (7)	104

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

Acknowledgements

The authors thank the National Natural Science Foundation of China (20671073), the Natural Science Foundation of Shandong (Y2007B60), the Science and Technology Foundation of Weifang and Weifang University for research grants.

References

Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tai, X.-S. & Feng, Y.-M. (2008). Acta Cryst. E64, o707. Web of Science CSD CrossRef IUCr Journals Google Scholar
Tai, X.-S., Feng, Y.-M. & Zhang, H.-X. (2008). Acta Cryst. E64, m502. Web of Science CSD CrossRef IUCr Journals Google Scholar
Tai, X. S., Yin, J. & Feng, Y. M. (2007). Z. Kristallogr. New Cryst. Struct. 222, 398–400. CAS Google Scholar
Tai, X. S., Yin, J., Feng, Y. M. & Kong, F. Y. (2007). Chin. J. Inorg. Chem. 23, 1812–1814. CAS Google Scholar
Tai, X.-S., Yin, J. & Hao, M.-Y. (2007). Acta Cryst. E63, m1061–m1062. Web of Science CSD CrossRef IUCr Journals Google Scholar
Tai, X.-S., Yin, X.-H., Tan, M.-Y. & Li, Y.-Z. (2003). Acta Cryst. E59, o681–o682. Web of Science CSD CrossRef IUCr Journals Google Scholar
Wang, L.-H., Yin, J. & Tai, X.-S. (2007). Acta Cryst. E63, m1664. Web of Science CSD CrossRef IUCr Journals Google Scholar