catena-Poly[[[triaqua­copper(II)]-μ-2,2′-bipyridine-3,3′-dicarboxyl­ato-κ3N,N′:O] monohydrate]

Wu, Q.; Wang, F.; Jiang, N.; Cao, L.; Pan, Q.

doi:10.1107/S1600536811046423

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 12| December 2011| Pages m1710-m1711

https://doi.org/10.1107/S1600536811046423

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catena-Poly[[[triaquacopper(II)]-μ-2,2′-bipyridine-3,3′-dicarboxylato-κ³N,N′:O] monohydrate]

Qihui Wu,^a Fuxiang Wang,^a Nanqing Jiang,^a Li Cao ^a and Qinhe Pan ^a ^*

^aDepartment of Materials and Chemical Engineering, Ministry of Education Key Laboratory of Application Technology of Hainan Superior Resources Chemical Materials, Hainan University, Haikou 570228, Hainan Province, People's Republic of China
^*Correspondence e-mail: panqinhe@163.com

(Received 12 October 2011; accepted 3 November 2011; online 9 November 2011)

The title compound, {[Cu(C₁₂H₆N₂O₄)(H₂O)₃]·H₂O}_n, was synthesized under hydrothermal conditions. The Cu²⁺ ion is six-coordinated by three water O atoms, and two N atoms and one O atom of the 2,2′-bipyridine-3,3′-dicarboxylate bridging ligand in a sligthly distorted octahedral environment. The 2,2-bipyridine-3,3′-dicarboxylate bridges link the Cu²⁺ ions into chains along the b-axis direction. These chains are further linked by O—H⋯O hydrogen bonds involving the water solvent molecules, forming a three-dimensional framework.

Related literature

For potential applications of coordination polymers in drug delivery, shape-selective sorption/separation and catalysis, see: Chen & Tong (2007 ); Zeng et al. (2009 ). Their structures vary from one-dimensional to three-dimensional architectures, see: Du & Bu (2009 ); Qiu & Zhu (2009 ). For our recent research on the synthesis of coordination polymers, see: Pan et al. (2010a ,b ,c , 2011 ).

Experimental

Crystal data

[Cu(C₁₂H₆N₂O₄)(H₂O)₃]·H₂O
M_r = 377.79
Monoclinic, P 2₁ /n
a = 9.950 (4) Å
b = 9.161 (4) Å
c = 15.974 (7) Å
β = 96.848 (8)°
V = 1445.7 (10) Å³
Z = 4
Mo Kα radiation
μ = 1.56 mm⁻¹
T = 296 K
0.30 × 0.18 × 0.15 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.722, T_max = 0.792
10263 measured reflections
3585 independent reflections
2268 reflections with I > 2σ(I)
R_int = 0.062

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.153
S = 1.08
3585 reflections
208 parameters
H-atom parameters constrained
Δρ_max = 1.02 e Å⁻³
Δρ_min = −1.13 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5A⋯O1Wⁱ	0.85	1.84	2.669 (5)	167
O5—H5⋯O4ⁱⁱ	0.85	1.86	2.689 (4)	167
O6—H6A⋯O3ⁱⁱⁱ	0.85	1.88	2.715 (5)	169
O6—H6⋯O1ⁱ	0.85	2.43	3.282 (5)	180
O7—H7A⋯O4ⁱ	0.85	1.80	2.642 (4)	170
O7—H7⋯O1ⁱⁱ	0.85	1.95	2.711 (4)	149
O1W—H1WA⋯O1	0.85	2.11	2.850 (5)	146
O1W—H1W⋯O3	0.85	2.01	2.854 (6)	170
Symmetry codes: (i) x-1, y, z; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); 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: https://doi.org/10.1107/S1600536811046423/yk2027sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811046423/yk2027Isup2.hkl

checkCIF report

Comment top

The design and synthesis of coordination polymers have attracted increasing attention in recent years because of their potential applications in drug delivery, shape-selective sorption/separation, and catalysis (Chen et al., 2007 and Zeng et al., 2009). Their structures vary from one-dimensional to three-dimensional architectures (Qiu et al., 2009 and Du et al., 2009). In our recent works, our research interest has been focused on the synthesis of coordination polymers (Pan et al., 2010a,b,c and 2011). Here we present a Cu-containing coordination polymer with one-dimensional chain structure.

As shown in Fig. 1, the asymmetric part of crystal structure of the title compound consists of an Cu atoms, a 2,2'-bipyridine-3,3'-dicarboxylate (bpdc) unit, three coordinated water molecules and one solvate water molecules. The Cu center is six-coordinated by four O atoms and two N atoms. Three of the four O atoms are from three coordination water molecules and the last one is from the carboxylate of the bpdc unit, whereas both N atoms are from the bridging bpdc unit. By this way, the Cu centers and the bpdc units form a chain-like structure, and these chains are further linked by hrydrogen bonds involving the solvent water molecules to from a three-dimensional superamolecular framework (see Table 1).

Related literature top

For potential applications of coordination polymers in drug delivery, shape-selective sorption/separation and catalysis, see: Chen & Tong (2007); Zeng et al. (2009). Their structures vary from one-dimensional to three-dimensional architectures, see: Du & Bu (2009); Qiu & Zhu (2009). For our recent research on the synthesis of coordination polymers, see: Pan et al. (2010a,b,c, 2011).

Experimental top

In a typical synthesis, a mixture of CuSO₄ (0.032 g), bpdc (0.026 g), NaOH (0.008 g), 2,2'-bipyridine (0.016 g) and H₂O (10 ml), was placed into a 25 ml Teflon-lined reactor under autogenous pressure at 100 °C for 3 days.

Structure description top

For potential applications of coordination polymers in drug delivery, shape-selective sorption/separation and catalysis, see: Chen & Tong (2007); Zeng et al. (2009). Their structures vary from one-dimensional to three-dimensional architectures, see: Du & Bu (2009); Qiu & Zhu (2009). For our recent research on the synthesis of coordination polymers, see: Pan et al. (2010a,b,c, 2011).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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. A view of the structure of complex. Ellipsoids are drawn at the 30% probability level. [Symmetry codes: (i) 1/2 - x, -1/2 + y, 1/2 - z; (ii) 1/2 - x, 1/2 - y, 1/2 - z.]

catena-Poly[[[triaquacopper(II)]-µ-2,2'-bipyridine-3,3'-dicarboxylato- κ³N,N':O] monohydrate] top

Crystal data top

[Cu(C₁₂H₆N₂O₄)(H₂O)₃]·H₂O	Z = 4
M_r = 377.79	F(000) = 772
Monoclinic, P2₁/n	D_x = 1.736 Mg m⁻³
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 9.950 (4) Å	θ = 1.0–28.4°
b = 9.161 (4) Å	µ = 1.56 mm⁻¹
c = 15.974 (7) Å	T = 296 K
β = 96.848 (8)°	Rod-like, blue
V = 1445.7 (10) Å³	0.3 × 0.18 × 0.15 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	3585 independent reflections
Radiation source: fine-focus sealed tube	2268 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.062
Detector resolution: 5.00 pixels mm^-1	θ_max = 28.4°, θ_min = 2.3°
phi and ω scans	h = −10→13
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −12→12
T_min = 0.722, T_max = 0.792	l = −21→21
10263 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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.153	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0663P)² + 0.4177P] where P = (F_o² + 2F_c²)/3
3585 reflections	(Δ/σ)_max < 0.001
208 parameters	Δρ_max = 1.02 e Å⁻³
0 restraints	Δρ_min = −1.13 e Å⁻³

Crystal data top

[Cu(C₁₂H₆N₂O₄)(H₂O)₃]·H₂O	V = 1445.7 (10) Å³
M_r = 377.79	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.950 (4) Å	µ = 1.56 mm⁻¹
b = 9.161 (4) Å	T = 296 K
c = 15.974 (7) Å	0.3 × 0.18 × 0.15 mm
β = 96.848 (8)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	3585 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2268 reflections with I > 2σ(I)
T_min = 0.722, T_max = 0.792	R_int = 0.062
10263 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	0 restraints
wR(F²) = 0.153	H-atom parameters constrained
S = 1.08	Δρ_max = 1.02 e Å⁻³
3585 reflections	Δρ_min = −1.13 e Å⁻³
208 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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	−0.03139 (5)	0.32126 (5)	0.24233 (3)	0.02945 (18)
O1	0.5391 (3)	0.5386 (4)	0.1205 (3)	0.0636 (12)
O2	0.4238 (3)	0.6377 (3)	0.21712 (17)	0.0274 (6)
O3	0.4864 (3)	0.2420 (4)	0.2535 (2)	0.0508 (9)
O4	0.6054 (3)	0.4033 (3)	0.3363 (2)	0.0453 (9)
O5	−0.1561 (3)	0.1917 (3)	0.1632 (2)	0.0487 (9)
H5A	−0.2390	0.2119	0.1489	0.058*
H5	−0.1267	0.1045	0.1642	0.058*
O6	−0.1426 (3)	0.5059 (3)	0.19990 (19)	0.0373 (7)
H6A	−0.1026	0.5863	0.2126	0.045*
H6	−0.2252	0.5142	0.1795	0.045*
O7	−0.1432 (3)	0.3074 (3)	0.3421 (2)	0.0375 (7)
H7A	−0.2269	0.3278	0.3398	0.045*
H7	−0.1294	0.2276	0.3689	0.045*
N1	0.1256 (3)	0.4331 (3)	0.31322 (19)	0.0232 (7)
N2	0.1029 (3)	0.3501 (3)	0.1547 (2)	0.0243 (7)
C1	0.0730 (4)	0.3334 (5)	0.0718 (3)	0.0346 (10)
H1	−0.0109	0.2945	0.0514	0.042*
C2	0.1597 (5)	0.3706 (6)	0.0152 (3)	0.0438 (12)
H2	0.1373	0.3541	−0.0422	0.053*
C3	0.2821 (5)	0.4335 (5)	0.0460 (3)	0.0399 (11)
H3	0.3430	0.4599	0.0088	0.048*
C4	0.3149 (4)	0.4575 (4)	0.1313 (2)	0.0264 (8)
C5	0.2231 (4)	0.4074 (4)	0.1854 (2)	0.0225 (8)
C6	0.2437 (4)	0.4159 (4)	0.2795 (2)	0.0230 (8)
C7	0.3662 (4)	0.4059 (4)	0.3308 (2)	0.0261 (9)
C8	0.3664 (4)	0.4325 (5)	0.4164 (3)	0.0370 (10)
H8	0.4477	0.4297	0.4517	0.044*
C9	0.2479 (5)	0.4629 (6)	0.4497 (3)	0.0420 (11)
H9	0.2483	0.4865	0.5063	0.050*
C10	0.1292 (4)	0.4572 (5)	0.3962 (3)	0.0336 (10)
H10	0.0479	0.4707	0.4186	0.040*
C11	0.4367 (4)	0.5507 (5)	0.1593 (3)	0.0335 (10)
C12	0.4963 (4)	0.3469 (4)	0.3029 (3)	0.0304 (9)
O1W	0.5895 (3)	0.2368 (4)	0.0943 (3)	0.0610 (11)
H1WA	0.5835	0.3265	0.0808	0.073*
H1W	0.5492	0.2392	0.1383	0.073*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0221 (3)	0.0281 (3)	0.0382 (3)	−0.0002 (2)	0.0039 (2)	0.0025 (2)
O1	0.054 (2)	0.065 (2)	0.082 (3)	−0.0323 (19)	0.051 (2)	−0.039 (2)
O2	0.0259 (14)	0.0270 (14)	0.0306 (15)	−0.0058 (12)	0.0086 (11)	−0.0046 (12)
O3	0.0329 (17)	0.044 (2)	0.076 (3)	0.0054 (15)	0.0063 (17)	−0.0190 (19)
O4	0.0202 (15)	0.0339 (17)	0.079 (3)	0.0038 (13)	−0.0036 (15)	−0.0010 (17)
O5	0.0301 (17)	0.0296 (17)	0.081 (3)	−0.0008 (13)	−0.0178 (16)	−0.0044 (16)
O6	0.0261 (15)	0.0325 (16)	0.0517 (19)	0.0042 (12)	−0.0018 (13)	0.0067 (14)
O7	0.0219 (14)	0.0347 (17)	0.058 (2)	0.0061 (12)	0.0150 (13)	0.0121 (14)
N1	0.0223 (16)	0.0232 (16)	0.0243 (17)	0.0012 (13)	0.0033 (13)	0.0001 (13)
N2	0.0232 (16)	0.0259 (17)	0.0237 (17)	−0.0036 (13)	0.0018 (13)	−0.0011 (13)
C1	0.034 (2)	0.038 (2)	0.031 (2)	−0.0079 (19)	0.0003 (18)	−0.0036 (19)
C2	0.057 (3)	0.049 (3)	0.026 (2)	−0.006 (2)	0.002 (2)	−0.006 (2)
C3	0.049 (3)	0.043 (3)	0.030 (2)	−0.008 (2)	0.016 (2)	−0.003 (2)
C4	0.027 (2)	0.026 (2)	0.028 (2)	−0.0050 (16)	0.0089 (16)	−0.0048 (16)
C5	0.0226 (18)	0.0193 (18)	0.026 (2)	0.0027 (15)	0.0040 (15)	−0.0014 (15)
C6	0.0201 (18)	0.0187 (18)	0.030 (2)	−0.0027 (15)	0.0026 (15)	−0.0003 (15)
C7	0.0236 (19)	0.0221 (19)	0.031 (2)	−0.0005 (15)	−0.0016 (16)	−0.0004 (16)
C8	0.033 (2)	0.040 (3)	0.034 (2)	−0.003 (2)	−0.0097 (19)	−0.001 (2)
C9	0.045 (3)	0.060 (3)	0.021 (2)	−0.007 (2)	0.0029 (19)	−0.003 (2)
C10	0.034 (2)	0.038 (2)	0.031 (2)	−0.0007 (19)	0.0101 (18)	−0.0053 (19)
C11	0.030 (2)	0.032 (2)	0.040 (3)	−0.0075 (18)	0.0146 (18)	−0.0015 (19)
C12	0.0213 (19)	0.025 (2)	0.044 (3)	0.0033 (16)	0.0005 (17)	0.0032 (18)
O1W	0.040 (2)	0.056 (2)	0.086 (3)	0.0137 (18)	0.0043 (19)	−0.014 (2)

Geometric parameters (Å, º) top

Cu1—O5	2.043 (3)	N2—C5	1.344 (5)
Cu1—O7	2.053 (3)	C1—C2	1.365 (6)
Cu1—O2ⁱ	2.056 (3)	C1—H1	0.9300
Cu1—N2	2.064 (3)	C2—C3	1.383 (6)
Cu1—N1	2.085 (3)	C2—H2	0.9300
Cu1—O6	2.090 (3)	C3—C4	1.380 (6)
O1—C11	1.259 (5)	C3—H3	0.9300
O2—C11	1.239 (5)	C4—C5	1.408 (5)
O2—Cu1ⁱⁱ	2.056 (3)	C4—C11	1.506 (5)
O3—C12	1.241 (5)	C5—C6	1.495 (5)
O4—C12	1.261 (5)	C6—C7	1.388 (5)
O5—H5A	0.8500	C7—C8	1.389 (6)
O5—H5	0.8500	C7—C12	1.518 (5)
O6—H6A	0.8501	C8—C9	1.379 (6)
O6—H6	0.8509	C8—H8	0.9300
O7—H7A	0.8500	C9—C10	1.373 (6)
O7—H7	0.8499	C9—H9	0.9300
N1—C10	1.341 (5)	C10—H10	0.9300
N1—C6	1.359 (5)	O1W—H1WA	0.8500
N2—C1	1.332 (5)	O1W—H1W	0.8500

O5—Cu1—O7	95.69 (14)	C1—C2—C3	117.9 (4)
O5—Cu1—O2ⁱ	88.56 (12)	C1—C2—H2	121.1
O7—Cu1—O2ⁱ	90.86 (11)	C3—C2—H2	121.1
O5—Cu1—N2	92.82 (14)	C4—C3—C2	120.8 (4)
O7—Cu1—N2	171.37 (12)	C4—C3—H3	119.6
O2ⁱ—Cu1—N2	87.91 (12)	C2—C3—H3	119.6
O5—Cu1—N1	169.05 (13)	C3—C4—C5	117.4 (4)
O7—Cu1—N1	92.80 (12)	C3—C4—C11	118.1 (4)
O2ⁱ—Cu1—N1	84.41 (12)	C5—C4—C11	124.1 (3)
N2—Cu1—N1	78.58 (12)	N2—C5—C4	121.2 (3)
O5—Cu1—O6	90.61 (12)	N2—C5—C6	113.4 (3)
O7—Cu1—O6	89.24 (11)	C4—C5—C6	125.4 (3)
O2ⁱ—Cu1—O6	179.16 (12)	N1—C6—C7	121.0 (4)
N2—Cu1—O6	92.12 (12)	N1—C6—C5	112.5 (3)
N1—Cu1—O6	96.42 (12)	C7—C6—C5	126.5 (3)
C11—O2—Cu1ⁱⁱ	131.7 (3)	C6—C7—C8	117.8 (4)
Cu1—O5—H5A	122.6	C6—C7—C12	124.8 (4)
Cu1—O5—H5	110.6	C8—C7—C12	116.7 (4)
H5A—O5—H5	122.0	C9—C8—C7	121.0 (4)
Cu1—O6—H6A	114.2	C9—C8—H8	119.5
Cu1—O6—H6	130.3	C7—C8—H8	119.5
H6A—O6—H6	114.7	C10—C9—C8	117.7 (4)
Cu1—O7—H7A	124.9	C10—C9—H9	121.2
Cu1—O7—H7	111.9	C8—C9—H9	121.2
H7A—O7—H7	108.0	N1—C10—C9	122.8 (4)
C10—N1—C6	119.2 (3)	N1—C10—H10	118.6
C10—N1—Cu1	123.3 (3)	C9—C10—H10	118.6
C6—N1—Cu1	110.8 (2)	O2—C11—O1	125.8 (4)
C1—N2—C5	119.4 (3)	O2—C11—C4	115.8 (3)
C1—N2—Cu1	125.1 (3)	O1—C11—C4	118.3 (4)
C5—N2—Cu1	115.0 (2)	O3—C12—O4	125.9 (4)
N2—C1—C2	123.1 (4)	O3—C12—C7	117.1 (4)
N2—C1—H1	118.4	O4—C12—C7	116.8 (4)
C2—C1—H1	118.4	H1WA—O1W—H1W	99.2

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···O1Wⁱⁱⁱ	0.85	1.84	2.669 (5)	167
O5—H5···O4ⁱ	0.85	1.86	2.689 (4)	167
O6—H6A···O3ⁱⁱ	0.85	1.88	2.715 (5)	169
O6—H6···O1ⁱⁱⁱ	0.85	2.43	3.282 (5)	180
O7—H7A···O4ⁱⁱⁱ	0.85	1.80	2.642 (4)	170
O7—H7···O1ⁱ	0.85	1.95	2.711 (4)	149
O1W—H1WA···O1	0.85	2.11	2.850 (5)	146
O1W—H1W···O3	0.85	2.01	2.854 (6)	170

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

Experimental details

Crystal data
Chemical formula	[Cu(C₁₂H₆N₂O₄)(H₂O)₃]·H₂O
M_r	377.79
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	9.950 (4), 9.161 (4), 15.974 (7)
β (°)	96.848 (8)
V (Å³)	1445.7 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.56
Crystal size (mm)	0.3 × 0.18 × 0.15

Data collection
Diffractometer	Bruker APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.722, 0.792
No. of measured, independent and observed [I > 2σ(I)] reflections	10263, 3585, 2268
R_int	0.062
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.153, 1.08
No. of reflections	3585
No. of parameters	208
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.02, −1.13

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), 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
O5—H5A···O1Wⁱ	0.85	1.84	2.669 (5)	166.5
O5—H5···O4ⁱⁱ	0.85	1.86	2.689 (4)	166.5
O6—H6A···O3ⁱⁱⁱ	0.85	1.88	2.715 (5)	169.4
O6—H6···O1ⁱ	0.85	2.43	3.282 (5)	179.7
O7—H7A···O4ⁱ	0.85	1.80	2.642 (4)	170.0
O7—H7···O1ⁱⁱ	0.85	1.95	2.711 (4)	148.6
O1W—H1WA···O1	0.85	2.11	2.850 (5)	145.7
O1W—H1W···O3	0.85	2.01	2.854 (6)	170.0

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

Acknowledgements

This work was supported by the National Natural Science Foundation of China (No. 21101047), the Natural Science Foundation of Hainan Province (No. 211010) and the Priming Scientific Research Foundation of Hainan University (No. kyqd1051).

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