catena-Poly[[diaqua­nickel(II)]-μ-7-oxabicyclo­[2.2.1]heptane-2,3-di­carboxyl­ato]

Wang, Y.-Y.; Hu, R.-D.; Zhu, W.-Z.; Lin, Q.-Y.

doi:10.1107/S1600536809021771

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 7| July 2009| Page m787

doi:10.1107/S1600536809021771

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catena-Poly[[diaquanickel(II)]-μ-7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylato]

Yun-Yun Wang,^a Rui-Ding Hu,^a Wen-Zhong Zhu ^a and Qiu-Yue Lin ^a ^*

^aZhejiang Key Laboratory for Reactive Chemistry on Solid Surfaces, Institute of Physical Chemistry, Zhejiang Normal University, Jinhua, Zhejiang 321004, People's Republic of China, and, College of Chemistry and Life Science, Zhejiang Normal University, Jinhua 321004, Zhejiang, People's Republic of China
^*Correspondence e-mail: sky51@zjnu.cn

(Received 25 May 2009; accepted 9 June 2009; online 17 June 2009)

In the crystal structure of the title compound, [Ni(C₈H₈O₅)(H₂O)₂]_n, the Ni^II cation is in a Jahn–Teller-distorted octahedral coordination environment binding to two O atoms from water molecules, the bridging O atom of the bicycloheptane unit, two carboxylate O atoms from different carboxylate groups and one carboxylate O atom from a symmetry-related bridging ligand. The crystal structure is made up from layers propagating parallel to the bc plane.

Related literature

For the structure of the Cu(II) analogue, see: Wang et al. (2009 ).

Experimental

Crystal data

[Ni(C₈H₈O₅)(H₂O)₂]
M_r = 278.89
Monoclinic, P 2₁ /c
a = 10.9145 (2) Å
b = 8.6281 (2) Å
c = 10.8581 (2) Å
β = 107.351 (1)°
V = 975.99 (3) Å³
Z = 4
Mo Kα radiation
μ = 2.01 mm⁻¹
T = 296 K
0.27 × 0.20 × 0.10 mm

Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.618, T_max = 0.817
7972 measured reflections
2213 independent reflections
1961 reflections with I > 2σ(I)
R_int = 0.019

Refinement

R[F² > 2σ(F²)] = 0.022
wR(F²) = 0.059
S = 1.02
2213 reflections
157 parameters
6 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WA⋯O2ⁱ	0.841 (15)	2.062 (15)	2.9027 (19)	180 (3)
O1W—H1WB⋯O3ⁱⁱ	0.822 (15)	2.135 (18)	2.7953 (17)	137 (2)
O1W—H1WB⋯O1ⁱⁱⁱ	0.822 (15)	2.366 (19)	3.1013 (17)	149 (2)
O2W—H2WA⋯O4ⁱ	0.824 (16)	1.888 (16)	2.6967 (19)	167 (3)
O2W—H2WB⋯O2ⁱⁱ	0.802 (16)	2.341 (16)	3.135 (2)	170 (2)
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) x, y+1, z.

Data collection: APEX2 (Bruker, 2006 ); cell refinement: SAINT (Bruker, 2006); 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: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809021771/at2793sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809021771/at2793Isup2.hkl

checkCIF report

Comment top

The title compound, (I), is isostructural with the Cu(II) analogue (Wang et al., 2009). In the title compound, each Ni^II ion is six-coordinated by two oxygen atoms from water, one bridge oxygen, two carboxylate oxygen atoms in two different carboxylate groups and one carboxylate oxygen atom in another asymmetric unit. O1, O1W, O5 and O3 lie in the equatorial plane with the torsion angle -1.121 (47)°. O2W and carboxylate oxygen atom O4 are in the axial positions. The bond angle of O2W—Ni1—O4 is 177.144 (52)°, so it forms a distorted octahedral. Owing to the binding of the bridge oxygen atom with Ni, two six-membered rings(Ni1/O4/C8/C6/C5/O5 and Ni1/O3/C7/C1/C2/O5) are created. In addition, a seven-membered ring (Ni1/O3/C7/C1/C6/C8/O4) is formed because of the coordination of carboxylate oxygen atoms O3 and O4. What's more, intermolecular O—H···O hydrogen bonds of the complex make the crystal structure more stable (Table 1).

Related literature top

For the structure of the Cu(II) analogue, see: Wang et al. (2009).

Experimental top

A mixture of 1 mmol norcantharidin, 1 mmol NiCl₂.6H₂O and 15 mL distilled water was sealed in a 25 mL Teflon-lined stainless vessel and heated at 443 K for 3 d, then cooled slowly to room temperature. The solution was filtered and block green crystals were obtained.

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); 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: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. A view of the molecule of (I) showing the atom-labelling scheme with displacement ellipsoids drawn at the 30% probability.

catena-Poly[[diaquanickel(II)]-µ-7-oxabicyclo[2.2.1]heptane-2,3- dicarboxylato] top

Crystal data top

[Ni(C₈H₈O₅)(H₂O)₂]	F(000) = 576
M_r = 278.89	D_x = 1.898 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4375 reflections
a = 10.9145 (2) Å	θ = 2.0–27.5°
b = 8.6281 (2) Å	µ = 2.01 mm⁻¹
c = 10.8581 (2) Å	T = 296 K
β = 107.351 (1)°	Block, green
V = 975.99 (3) Å³	0.27 × 0.20 × 0.10 mm
Z = 4

Data collection top

Bruker APEXII area-detector diffractometer	2213 independent reflections
Radiation source: fine-focus sealed tube	1961 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
ω scans	θ_max = 27.5°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→14
T_min = 0.618, T_max = 0.817	k = −11→6
7972 measured reflections	l = −12→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)] = 0.022	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.059	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.032P)² + 0.4246P] where P = (F_o² + 2F_c²)/3
2213 reflections	(Δ/σ)_max = 0.001
157 parameters	Δρ_max = 0.30 e Å⁻³
6 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

[Ni(C₈H₈O₅)(H₂O)₂]	V = 975.99 (3) Å³
M_r = 278.89	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.9145 (2) Å	µ = 2.01 mm⁻¹
b = 8.6281 (2) Å	T = 296 K
c = 10.8581 (2) Å	0.27 × 0.20 × 0.10 mm
β = 107.351 (1)°

Data collection top

Bruker APEXII area-detector diffractometer	2213 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1961 reflections with I > 2σ(I)
T_min = 0.618, T_max = 0.817	R_int = 0.019
7972 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.022	6 restraints
wR(F²) = 0.059	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.30 e Å⁻³
2213 reflections	Δρ_min = −0.30 e Å⁻³
157 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	0.73787 (15)	−0.1019 (2)	0.71021 (15)	0.0214 (3)
H1A	0.7710	−0.2053	0.7005	0.026*
C2	0.75289 (16)	0.0067 (2)	0.60404 (16)	0.0234 (3)
H2A	0.6816	0.0008	0.5240	0.028*
C3	0.88388 (17)	−0.0131 (2)	0.58426 (19)	0.0329 (4)
H3A	0.8888	0.0402	0.5072	0.039*
H3B	0.9048	−0.1216	0.5789	0.039*
C4	0.97214 (18)	0.0632 (3)	0.7078 (2)	0.0375 (5)
H4A	1.0324	−0.0110	0.7599	0.045*
H4B	1.0192	0.1498	0.6872	0.045*
C5	0.87589 (15)	0.1175 (2)	0.77610 (17)	0.0265 (4)
H5A	0.9073	0.2034	0.8363	0.032*
C6	0.82547 (16)	−0.0207 (2)	0.83620 (16)	0.0234 (3)
H6A	0.8966	−0.0891	0.8805	0.028*
C7	0.59962 (14)	−0.1119 (2)	0.71114 (15)	0.0202 (3)
C8	0.75095 (16)	0.0292 (2)	0.92900 (15)	0.0242 (4)
O1W	0.69190 (12)	0.44064 (15)	0.74994 (13)	0.0289 (3)
H1WA	0.711 (2)	0.473 (3)	0.6846 (18)	0.043*
H1WB	0.643 (2)	0.505 (2)	0.765 (2)	0.043*
O1	0.56501 (12)	−0.23749 (14)	0.74852 (12)	0.0244 (3)
O2W	0.51314 (14)	0.29376 (19)	0.53124 (13)	0.0383 (3)
H2WA	0.557 (2)	0.322 (3)	0.486 (2)	0.057*
H2WB	0.4472 (17)	0.342 (3)	0.512 (2)	0.057*
O2	0.75780 (15)	−0.05131 (17)	1.02529 (12)	0.0389 (3)
O3	0.52811 (11)	0.00446 (14)	0.67765 (13)	0.0272 (3)
O4	0.68270 (12)	0.15134 (16)	0.89954 (11)	0.0302 (3)
O5	0.76514 (11)	0.15762 (14)	0.66735 (11)	0.0236 (3)
Ni1	0.601796 (19)	0.22532 (2)	0.714683 (19)	0.01937 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0213 (8)	0.0212 (8)	0.0245 (8)	0.0010 (6)	0.0109 (6)	−0.0017 (6)
C2	0.0216 (8)	0.0296 (9)	0.0221 (8)	−0.0007 (7)	0.0111 (6)	−0.0032 (7)
C3	0.0287 (9)	0.0413 (11)	0.0364 (10)	0.0019 (8)	0.0217 (8)	−0.0008 (8)
C4	0.0218 (9)	0.0503 (13)	0.0452 (11)	−0.0038 (8)	0.0172 (8)	0.0003 (10)
C5	0.0196 (8)	0.0318 (10)	0.0285 (9)	−0.0051 (7)	0.0080 (7)	−0.0037 (7)
C6	0.0194 (7)	0.0285 (9)	0.0225 (8)	0.0031 (7)	0.0066 (6)	0.0014 (7)
C7	0.0218 (8)	0.0217 (8)	0.0194 (8)	−0.0035 (6)	0.0098 (6)	−0.0058 (6)
C8	0.0240 (8)	0.0299 (9)	0.0181 (8)	−0.0004 (7)	0.0053 (6)	−0.0013 (7)
O1W	0.0290 (7)	0.0249 (7)	0.0357 (7)	0.0008 (5)	0.0145 (6)	−0.0014 (5)
O1	0.0236 (6)	0.0228 (6)	0.0306 (6)	−0.0026 (5)	0.0138 (5)	0.0003 (5)
O2W	0.0377 (8)	0.0566 (10)	0.0238 (7)	0.0112 (7)	0.0144 (6)	0.0103 (6)
O2	0.0555 (9)	0.0399 (8)	0.0258 (7)	0.0123 (7)	0.0187 (6)	0.0097 (6)
O3	0.0220 (6)	0.0209 (6)	0.0421 (7)	−0.0007 (5)	0.0145 (5)	−0.0011 (5)
O4	0.0364 (7)	0.0357 (8)	0.0218 (6)	0.0119 (6)	0.0137 (5)	0.0046 (5)
O5	0.0234 (6)	0.0249 (6)	0.0254 (6)	0.0001 (5)	0.0118 (5)	0.0019 (5)
Ni1	0.02056 (12)	0.02009 (13)	0.01992 (12)	0.00083 (8)	0.00979 (9)	0.00170 (8)

Geometric parameters (Å, º) top

C1—C7	1.514 (2)	C6—H6A	0.9800
C1—C2	1.532 (2)	C7—O1	1.254 (2)
C1—C6	1.580 (2)	C7—O3	1.257 (2)
C1—H1A	0.9800	C8—O2	1.239 (2)
C2—O5	1.460 (2)	C8—O4	1.275 (2)
C2—C3	1.517 (2)	O1W—Ni1	2.0834 (13)
C2—H2A	0.9800	O1W—H1WA	0.841 (15)
C3—C4	1.546 (3)	O1W—H1WB	0.822 (15)
C3—H3A	0.9700	O1—Ni1ⁱ	2.0027 (12)
C3—H3B	0.9700	O2W—Ni1	2.0255 (13)
C4—C5	1.529 (2)	O2W—H2WA	0.824 (16)
C4—H4A	0.9700	O2W—H2WB	0.802 (16)
C4—H4B	0.9700	O3—Ni1	2.0608 (12)
C5—O5	1.457 (2)	O4—Ni1	2.0393 (12)
C5—C6	1.538 (2)	O5—Ni1	2.0809 (11)
C5—H5A	0.9800	Ni1—O1ⁱⁱ	2.0027 (12)
C6—C8	1.533 (2)

C7—C1—C2	111.72 (13)	C1—C6—H6A	110.1
C7—C1—C6	111.48 (13)	O1—C7—O3	124.24 (14)
C2—C1—C6	101.96 (13)	O1—C7—C1	116.61 (15)
C7—C1—H1A	110.5	O3—C7—C1	119.13 (15)
C2—C1—H1A	110.5	O2—C8—O4	123.98 (16)
C6—C1—H1A	110.5	O2—C8—C6	119.16 (16)
O5—C2—C3	102.07 (14)	O4—C8—C6	116.85 (14)
O5—C2—C1	101.93 (12)	Ni1—O1W—H1WA	110.9 (17)
C3—C2—C1	110.77 (14)	Ni1—O1W—H1WB	109.8 (17)
O5—C2—H2A	113.6	H1WA—O1W—H1WB	106.5 (19)
C3—C2—H2A	113.6	C7—O1—Ni1ⁱ	125.62 (11)
C1—C2—H2A	113.6	Ni1—O2W—H2WA	119.0 (17)
C2—C3—C4	101.47 (14)	Ni1—O2W—H2WB	122.3 (17)
C2—C3—H3A	111.5	H2WA—O2W—H2WB	109 (2)
C4—C3—H3A	111.5	C7—O3—Ni1	120.63 (11)
C2—C3—H3B	111.5	C8—O4—Ni1	123.69 (11)
C4—C3—H3B	111.5	C5—O5—C2	96.15 (13)
H3A—C3—H3B	109.3	C5—O5—Ni1	115.54 (9)
C5—C4—C3	102.17 (14)	C2—O5—Ni1	113.69 (9)
C5—C4—H4A	111.3	O1ⁱⁱ—Ni1—O2W	87.33 (6)
C3—C4—H4A	111.3	O1ⁱⁱ—Ni1—O4	90.36 (5)
C5—C4—H4B	111.3	O2W—Ni1—O4	177.14 (6)
C3—C4—H4B	111.3	O1ⁱⁱ—Ni1—O3	82.07 (5)
H4A—C4—H4B	109.2	O2W—Ni1—O3	91.92 (6)
O5—C5—C4	101.75 (14)	O4—Ni1—O3	86.09 (5)
O5—C5—C6	102.27 (13)	O1ⁱⁱ—Ni1—O5	172.30 (5)
C4—C5—C6	110.67 (16)	O2W—Ni1—O5	91.84 (5)
O5—C5—H5A	113.7	O4—Ni1—O5	90.22 (5)
C4—C5—H5A	113.7	O3—Ni1—O5	90.31 (5)
C6—C5—H5A	113.7	O1ⁱⁱ—Ni1—O1W	103.17 (5)
C8—C6—C5	112.87 (15)	O2W—Ni1—O1W	88.95 (6)
C8—C6—C1	113.00 (13)	O4—Ni1—O1W	93.22 (5)
C5—C6—C1	100.21 (13)	O3—Ni1—O1W	174.73 (5)
C8—C6—H6A	110.1	O5—Ni1—O1W	84.46 (5)
C5—C6—H6A	110.1

C7—C1—C2—O5	85.11 (15)	C6—C8—O4—Ni1	28.8 (2)
C6—C1—C2—O5	−34.06 (14)	C4—C5—O5—C2	56.04 (15)
C7—C1—C2—C3	−166.92 (14)	C6—C5—O5—C2	−58.43 (14)
C6—C1—C2—C3	73.92 (16)	C4—C5—O5—Ni1	176.00 (11)
O5—C2—C3—C4	35.96 (17)	C6—C5—O5—Ni1	61.53 (14)
C1—C2—C3—C4	−71.93 (18)	C3—C2—O5—C5	−57.44 (14)
C2—C3—C4—C5	−1.3 (2)	C1—C2—O5—C5	57.12 (13)
C3—C4—C5—O5	−33.65 (19)	C3—C2—O5—Ni1	−178.84 (10)
C3—C4—C5—C6	74.44 (18)	C1—C2—O5—Ni1	−64.27 (13)
O5—C5—C6—C8	−84.19 (16)	C8—O4—Ni1—O1ⁱⁱ	133.87 (14)
C4—C5—C6—C8	168.06 (15)	C8—O4—Ni1—O2W	97.8 (11)
O5—C5—C6—C1	36.27 (15)	C8—O4—Ni1—O3	51.85 (14)
C4—C5—C6—C1	−71.48 (16)	C8—O4—Ni1—O5	−38.45 (14)
C7—C1—C6—C8	−0.2 (2)	C8—O4—Ni1—O1W	−122.91 (14)
C2—C1—C6—C8	119.17 (15)	C7—O3—Ni1—O1ⁱⁱ	−141.13 (13)
C7—C1—C6—C5	−120.54 (14)	C7—O3—Ni1—O2W	131.83 (12)
C2—C1—C6—C5	−1.20 (15)	C7—O3—Ni1—O4	−50.22 (12)
C2—C1—C7—O1	149.60 (15)	C7—O3—Ni1—O5	39.98 (12)
C6—C1—C7—O1	−97.04 (17)	C7—O3—Ni1—O1W	32.4 (6)
C2—C1—C7—O3	−31.8 (2)	C5—O5—Ni1—O1ⁱⁱ	−105.7 (4)
C6—C1—C7—O3	81.59 (18)	C2—O5—Ni1—O1ⁱⁱ	4.1 (4)
C5—C6—C8—O2	−145.66 (17)	C5—O5—Ni1—O2W	170.59 (12)
C1—C6—C8—O2	101.50 (19)	C2—O5—Ni1—O2W	−79.56 (11)
C5—C6—C8—O4	35.8 (2)	C5—O5—Ni1—O4	−11.38 (12)
C1—C6—C8—O4	−77.0 (2)	C2—O5—Ni1—O4	98.46 (11)
O3—C7—O1—Ni1ⁱ	−8.3 (2)	C5—O5—Ni1—O3	−97.47 (11)
C1—C7—O1—Ni1ⁱ	170.29 (10)	C2—O5—Ni1—O3	12.37 (10)
O1—C7—O3—Ni1	145.58 (13)	C5—O5—Ni1—O1W	81.83 (12)
C1—C7—O3—Ni1	−32.95 (18)	C2—O5—Ni1—O1W	−168.33 (11)
O2—C8—O4—Ni1	−149.69 (15)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O2ⁱⁱⁱ	0.84 (2)	2.06 (2)	2.9027 (19)	180 (3)
O1W—H1WB···O3ⁱⁱ	0.82 (2)	2.14 (2)	2.7953 (17)	137 (2)
O1W—H1WB···O1^iv	0.82 (2)	2.37 (2)	3.1013 (17)	149 (2)
O2W—H2WA···O4ⁱⁱⁱ	0.82 (2)	1.89 (2)	2.6967 (19)	167 (3)
O2W—H2WB···O2ⁱⁱ	0.80 (2)	2.34 (2)	3.135 (2)	170 (2)

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

Experimental details

Crystal data
Chemical formula	[Ni(C₈H₈O₅)(H₂O)₂]
M_r	278.89
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	10.9145 (2), 8.6281 (2), 10.8581 (2)
β (°)	107.351 (1)
V (Å³)	975.99 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.01
Crystal size (mm)	0.27 × 0.20 × 0.10

Data collection
Diffractometer	Bruker APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.618, 0.817
No. of measured, independent and observed [I > 2σ(I)] reflections	7972, 2213, 1961
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.022, 0.059, 1.02
No. of reflections	2213
No. of parameters	157
No. of restraints	6
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.30

Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2006), 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
O1W—H1WA···O2ⁱ	0.841 (15)	2.062 (15)	2.9027 (19)	180 (3)
O1W—H1WB···O3ⁱⁱ	0.822 (15)	2.135 (18)	2.7953 (17)	137 (2)
O1W—H1WB···O1ⁱⁱⁱ	0.822 (15)	2.366 (19)	3.1013 (17)	149 (2)
O2W—H2WA···O4ⁱ	0.824 (16)	1.888 (16)	2.6967 (19)	167 (3)
O2W—H2WB···O2ⁱⁱ	0.802 (16)	2.341 (16)	3.135 (2)	170 (2)

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

Acknowledgements

The authors thank the Natural Science Foundation of Zhejiang Province, China (grant No. Y407301) for financial support.

References

Bruker (2006). SAINT and APEX2. 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
Wang, Y.-Y., Hu, R.-D. & Wang, Y.-J. (2009). Acta Cryst. E65, m169. Web of Science CSD CrossRef IUCr Journals Google Scholar

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