Bis(μ-5-nitro-2-oxidobenzoato)bis­[triaqua­zinc(II)]

Li, Q.-S.; Yin, M.; Wei, H.; Zhou, G.-J.

doi:10.1107/S1600536809045607

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page m1516

doi:10.1107/S1600536809045607

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Bis(μ-5-nitro-2-oxidobenzoato)bis[triaquazinc(II)]

Qing-Shan Li,^a ^* Ma Yin,^a Hong Wei ^a and Guang-Ju Zhou ^a

^aKey Laboratory of Metastable Materials Science and Technology, College of Materials Science and Engineering, Yanshan University, Qinhuangdao, Hebei Province 066004, People's Republic of China
^*Correspondence e-mail: qsli@ysu.edu.cn

(Received 14 October 2009; accepted 30 October 2009; online 4 November 2009)

The title complex molecule, [Zn₂(C₇H₃NO₅)₂(H₂O)₆], is a centrosymmetric dimer containing two zinc(II) cations with distorted octahedral geometries provided by the O atoms of three water molecules and the two bridging bidentate 5-nitrosalicylate ligands. The separation between the metal centres in the dimer is 3.1790 (11) Å. The crystal structure is stabilized by O—H⋯O hydrogen bonds, one of which intradimeric, linking the dimers into a three-dimensional network.

Related literature

For examples of bonding modes exhibited by salicylate anions, see: Klug et al. (1958 ); Risannen et al. (1987 ); Charles et al. (1983 ); Jagner et al. (1976 ); Fu et al. (2005 ). For the crystal structures of 5-nitrosalicylate zinc(II) complexes, see: Tahir et al. (1997 ); Morgant et al. (2006 ); Erxleben (2001 ).

Experimental

Crystal data

[Zn₂(C₇H₃NO₅)₂(H₂O)₆]
M_r = 601.04
Monoclinic, P 2₁ /c
a = 10.858 (3) Å
b = 13.645 (3) Å
c = 6.6367 (17) Å
β = 91.887 (4)°
V = 982.7 (4) Å³
Z = 2
Mo Kα radiation
μ = 2.53 mm⁻¹
T = 294 K
0.26 × 0.10 × 0.08 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ) T_min = 0.752, T_max = 0.821
5435 measured reflections
2009 independent reflections
1418 reflections with I > 2σ(I)
R_int = 0.041

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.088
S = 1.03
2009 reflections
154 parameters
H-atom parameters constrained
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.55 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O8—H8B⋯O3ⁱ	0.84	1.81	2.651 (3)	173
O8—H8A⋯O5ⁱⁱ	0.85	2.26	3.038 (4)	153
O7—H7A⋯O8ⁱⁱⁱ	0.85	2.58	3.023 (4)	114
O7—H7B⋯O1^iv	0.85	1.77	2.596 (4)	163
O6—H6B⋯O4^v	0.85	1.87	2.696 (4)	164
O6—H6A⋯O8^vi	0.85	2.30	3.135 (5)	168
Symmetry codes: (i) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (ii) -x+2, -y+1, -z+1; (iii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (iv) -x+1, -y+1, -z+1; (v) x-1, y, z; (vi) x, y, z-1.

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1997); 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/S1600536809045607/rz2375sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809045607/rz2375Isup2.hkl

checkCIF report

Comment top

From a coordination standpoint, salicylate is a versatile ligand displaying a variety of bonding modes. For example, mono-deprotonation of salicylic acid normally leads to complexes containing the coordinated 2-HOC₆H₄CO₂ (salH) anion. This anion is known to bond to metals as a unidentate carboxylate e.g. in [Zn(salH)₂(H₂O)₂] (Klug et al. 1958; Risannen et al., 1987), as a bidentate chelating carboxylate e.g. in [Cd₂(salH)₄(H₂O)₄] (Charles et al. 1983), as a bidentate chelating ligand using one carboxylate oxygen and the hydroxyl oxygen e.g. in [Cu(salH)₂].2H₂O (Jagner et al., 1976). On the other hand, deprotonation of both the hydroxyl and carboxyl protons from the parent acid generates the [OC₆H₄CO₂]^2-(sal^2-) anion, which can be found chelating through the phenolate oxygen and one of the carboxyl O atoms as in [Ti(sal)₃]^2- (Fu, et al., 2005).

Although many complexes which use salicylate as ligand have been synthesized, two structures coming out from the reaction of the 5-nitrosalicylic acid with zinc salt are known to us: a tetrahydrate (Tahir et al., 1997), in an approximately octahedral geometry around the metal surrounding O atoms from four water ligands and two unidentate monoanionic 5-nitrosalicylate ligands using one carboxylate oxygen and a pentahydrate (Morgant, et al., 2006), penta-aqua-(5-nitrosalicylato-O)-zinc(ii) 5-nitrosalicylate monohydrate, in which the metal is coordinated by five water ligands and one carboxylato O-atom from the 5-nitrosalicylato ligand. Interestingly, the title binuclear complex presents a third, different structure, being an hexahydrate dimer with its two zinc(II) atoms bridged by two carboxylate O atoms.

The structure of the title compounds is shown in Fig. 1. The distorted octahedral environment of each zinc(II) cation is defined by three O atoms from three water molecules, another two (the phenolate and a carboxylate one) from a chelating 5-nitrosalicylate and the centrosymmetric image of the latter. These two carboxylate O atoms bridge neighbouring zinc cations into a planar, four-membered matallacycle resulting in a Zn1···Zn1ⁱ (see Fig 1 for symmetry codes) separation of 3.1790 (11) Å. It is the shortest of separation of Zn···Zn as reported previously in binuclear and tetranuclear zinc complex with salicylate ligands (Erxleben, 2001) It is worth mentioning that the use of a carboxylate oxygen as a bridging atom in salicylate metal complexes is rare; the title binuclear complex appears to be the first example of this behaviour in zinc complexes.

The carboxy group C1/O1/O2 as well as the nitro group N1/O4/O5 are effectively coplanar to the aromatic ring in the ligand as well as to the central Zn1/O2/C1/C2/C7/O3 six-membered ring generated upon coordination. The centrosymmetric character of the binuclear unit results in a large planar group composed of the two almost planar chelating ligands, the two zinc atoms and two O atoms from two aqua; the O atoms atoms from the remaining four aqua present Zn—O bonds almost orthogonal to this plane.

There are a number O—H···O hydrogen bonds stabilizing the structure (Table 1). The interaction involving O7—H7B and O1ⁱ is intradimeric and coplanar to the dimer mean plane. The remainig ones define a three-dimensional framework.

Related literature top

For examples of bonding modes exhibited by salicylate anions, see: Klug et al. (1958); Risannen et al. (1987); Charles et al. (1983); Jagner et al. (1976); Fu, et al. (2005). For the crystal structures of 5-nitrosalicylate zinc(II) complexes, see: Tahir et al. (1997); Morgant et al. (2006); Erxleben (2001).

Experimental top

The title complex was prepared by digesting a mixture of 5-nitrosalicylic acid (5 mmol) and fresh zinc hydroxide (10 mmol) in distilled water (30 ml) at 80 °C under stirring for 10 min. After filtration yellow-green crystals grew out of the solution by slow evaporation over a period of three days at room temperature. The starting zinc hydroxide was prepared from 50 ml aqueous solutions of 0.9 g of zinc chloride and 0.5 g of sodium hydroxide.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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 compound, with the atom-numbering scheme, and 30% probability displacement ellipsoids. H atoms are shown as small spheres of arbitrary radii and hydrogen bonds are indicated by dashed lines. [Symmetry code: (i) -x + 1, -y + 1, -z + 1.]

Bis(µ-5-nitro-2-oxidobenzoato)bis[triaquazinc(II)] top

Crystal data top

[Zn₂(C₇H₃NO₅)₂(H₂O)₆]	F(000) = 608
M_r = 601.04	D_x = 2.031 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1942 reflections
a = 10.858 (3) Å	θ = 2.4–25.8°
b = 13.645 (3) Å	µ = 2.53 mm⁻¹
c = 6.6367 (17) Å	T = 294 K
β = 91.887 (4)°	Block, yellow-green
V = 982.7 (4) Å³	0.26 × 0.10 × 0.08 mm
Z = 2

Data collection top

Bruker SMART CCD area-detector diffractometer	2009 independent reflections
Radiation source: fine-focus sealed tube	1418 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.041
ϕ and ω scans	θ_max = 26.4°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	h = −13→13
T_min = 0.752, T_max = 0.821	k = −17→12
5435 measured reflections	l = −8→8

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.088	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0314P)² + 1.0942P] where P = (F_o² + 2F_c²)/3
2009 reflections	(Δ/σ)_max = 0.001
154 parameters	Δρ_max = 0.45 e Å⁻³
0 restraints	Δρ_min = −0.55 e Å⁻³

Crystal data top

[Zn₂(C₇H₃NO₅)₂(H₂O)₆]	V = 982.7 (4) Å³
M_r = 601.04	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.858 (3) Å	µ = 2.53 mm⁻¹
b = 13.645 (3) Å	T = 294 K
c = 6.6367 (17) Å	0.26 × 0.10 × 0.08 mm
β = 91.887 (4)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2009 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	1418 reflections with I > 2σ(I)
T_min = 0.752, T_max = 0.821	R_int = 0.041
5435 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.088	H-atom parameters constrained
S = 1.03	Δρ_max = 0.45 e Å⁻³
2009 reflections	Δρ_min = −0.55 e Å⁻³
154 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
Zn1	0.52129 (4)	0.61159 (3)	0.44189 (8)	0.03665 (16)
O1	0.7644 (3)	0.37686 (19)	0.3938 (5)	0.0555 (9)
O2	0.6145 (2)	0.48166 (16)	0.4439 (4)	0.0310 (6)
O3	0.6603 (2)	0.67583 (17)	0.3118 (4)	0.0364 (6)
O4	1.2058 (2)	0.6122 (2)	0.1104 (5)	0.0506 (8)
O5	1.1653 (2)	0.4656 (2)	0.2105 (4)	0.0393 (7)
O6	0.4498 (3)	0.5753 (2)	0.1270 (5)	0.0564 (8)
H6A	0.4933	0.5848	0.0249	0.068*
H6B	0.3721	0.5766	0.1097	0.068*
O7	0.4029 (3)	0.72837 (19)	0.4384 (5)	0.0507 (8)
H7B	0.3400	0.7042	0.4931	0.061*
H7A	0.3907	0.7724	0.3504	0.061*
O8	0.5896 (3)	0.64083 (19)	0.7437 (4)	0.0493 (8)
H8A	0.6412	0.5961	0.7716	0.059*
H8B	0.6131	0.6997	0.7546	0.059*
N1	1.1340 (3)	0.5505 (2)	0.1763 (5)	0.0333 (7)
C1	0.7233 (3)	0.4611 (2)	0.3858 (5)	0.0271 (8)
C2	0.8053 (3)	0.5409 (2)	0.3128 (5)	0.0242 (7)
C3	0.9258 (3)	0.5143 (3)	0.2764 (5)	0.0273 (8)
H3	0.9503	0.4496	0.2969	0.033*
C4	1.0097 (3)	0.5813 (3)	0.2108 (5)	0.0281 (8)
C5	0.9774 (3)	0.6787 (3)	0.1786 (6)	0.0333 (9)
H5A	1.0350	0.7236	0.1346	0.040*
C6	0.8604 (3)	0.7068 (3)	0.2126 (6)	0.0336 (9)
H6	0.8387	0.7719	0.1905	0.040*
C7	0.7692 (3)	0.6412 (2)	0.2803 (5)	0.0268 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0288 (2)	0.0205 (2)	0.0615 (3)	−0.00197 (18)	0.01434 (19)	−0.0010 (2)
O1	0.0525 (18)	0.0247 (16)	0.092 (2)	0.0100 (12)	0.0359 (17)	0.0158 (15)
O2	0.0268 (13)	0.0184 (12)	0.0483 (17)	−0.0017 (10)	0.0091 (11)	−0.0007 (11)
O3	0.0268 (14)	0.0236 (13)	0.0593 (19)	0.0032 (10)	0.0096 (12)	0.0079 (12)
O4	0.0274 (14)	0.0560 (19)	0.069 (2)	−0.0043 (14)	0.0138 (13)	0.0088 (16)
O5	0.0314 (14)	0.0428 (17)	0.0436 (17)	0.0106 (12)	0.0012 (12)	0.0017 (13)
O6	0.0329 (16)	0.076 (2)	0.060 (2)	−0.0017 (15)	0.0045 (14)	−0.0002 (17)
O7	0.0429 (17)	0.0279 (16)	0.082 (2)	0.0012 (12)	0.0102 (16)	0.0103 (14)
O8	0.064 (2)	0.0238 (14)	0.061 (2)	−0.0075 (13)	0.0134 (15)	−0.0095 (13)
N1	0.0264 (16)	0.044 (2)	0.0293 (18)	−0.0002 (14)	0.0000 (13)	−0.0024 (14)
C1	0.0311 (19)	0.0213 (18)	0.029 (2)	0.0013 (14)	0.0042 (15)	−0.0004 (14)
C2	0.0243 (17)	0.0244 (18)	0.0240 (19)	−0.0004 (13)	0.0021 (14)	0.0008 (14)
C3	0.032 (2)	0.0263 (19)	0.023 (2)	0.0022 (14)	0.0015 (15)	0.0017 (15)
C4	0.0221 (17)	0.039 (2)	0.023 (2)	0.0008 (14)	0.0012 (14)	0.0003 (15)
C5	0.0287 (19)	0.034 (2)	0.037 (2)	−0.0037 (15)	0.0050 (16)	0.0027 (17)
C6	0.035 (2)	0.0226 (19)	0.044 (2)	0.0003 (15)	0.0051 (17)	0.0069 (16)
C7	0.0271 (18)	0.0243 (18)	0.029 (2)	0.0021 (14)	0.0036 (14)	0.0015 (14)

Geometric parameters (Å, º) top

Zn1—O3	1.969 (2)	O7—H7A	0.8457
Zn1—O2	2.041 (2)	O8—H8A	0.8452
Zn1—O7	2.047 (3)	O8—H8B	0.8448
Zn1—O2ⁱ	2.107 (2)	N1—C4	1.440 (4)
Zn1—O8	2.150 (3)	C1—C2	1.497 (5)
Zn1—O6	2.260 (3)	C2—C3	1.386 (5)
O1—C1	1.234 (4)	C2—C7	1.439 (5)
O2—C1	1.285 (4)	C3—C4	1.372 (5)
O3—C7	1.297 (4)	C3—H3	0.9300
O4—N1	1.237 (4)	C4—C5	1.389 (5)
O5—N1	1.226 (4)	C5—C6	1.353 (5)
O6—H6A	0.8486	C5—H5A	0.9300
O6—H6B	0.8486	C6—C7	1.418 (5)
O7—H7B	0.8511	C6—H6	0.9300

O3—Zn1—O2	90.14 (10)	Zn1—O8—H8B	110.5
O3—Zn1—O7	97.96 (11)	H8A—O8—H8B	118.1
O2—Zn1—O7	170.84 (10)	O5—N1—O4	122.3 (3)
O3—Zn1—O2ⁱ	169.08 (10)	O5—N1—C4	120.1 (3)
O2—Zn1—O2ⁱ	79.97 (10)	O4—N1—C4	117.5 (3)
O7—Zn1—O2ⁱ	91.59 (11)	O1—C1—O2	121.7 (3)
O3—Zn1—O8	94.59 (11)	O1—C1—C2	118.2 (3)
O2—Zn1—O8	89.95 (11)	O2—C1—C2	120.1 (3)
O7—Zn1—O8	93.63 (12)	C3—C2—C7	118.5 (3)
O2ⁱ—Zn1—O8	90.07 (10)	C3—C2—C1	116.2 (3)
O3—Zn1—O6	86.38 (11)	C7—C2—C1	125.4 (3)
O2—Zn1—O6	88.33 (11)	C4—C3—C2	121.4 (3)
O7—Zn1—O6	87.93 (12)	C4—C3—H3	119.3
O2ⁱ—Zn1—O6	88.69 (11)	C2—C3—H3	119.3
O8—Zn1—O6	178.03 (11)	C3—C4—C5	121.3 (3)
C1—O2—Zn1	130.4 (2)	C3—C4—N1	119.4 (3)
C1—O2—Zn1ⁱ	129.6 (2)	C5—C4—N1	119.2 (3)
Zn1—O2—Zn1ⁱ	100.03 (10)	C6—C5—C4	118.6 (3)
C7—O3—Zn1	128.7 (2)	C6—C5—H5A	120.7
Zn1—O6—H6A	121.5	C4—C5—H5A	120.7
Zn1—O6—H6B	115.5	C5—C6—C7	122.9 (3)
H6A—O6—H6B	117.7	C5—C6—H6	118.5
Zn1—O7—H7B	101.9	C7—C6—H6	118.5
Zn1—O7—H7A	130.2	O3—C7—C6	118.1 (3)
H7B—O7—H7A	117.4	O3—C7—C2	124.6 (3)
Zn1—O8—H8A	106.0	C6—C7—C2	117.3 (3)

O3—Zn1—O2—C1	2.4 (3)	O2—C1—C2—C7	−6.9 (5)
O2ⁱ—Zn1—O2—C1	177.8 (4)	C7—C2—C3—C4	0.0 (5)
O8—Zn1—O2—C1	−92.1 (3)	C1—C2—C3—C4	−179.4 (3)
O6—Zn1—O2—C1	88.8 (3)	C2—C3—C4—C5	0.1 (6)
O3—Zn1—O2—Zn1ⁱ	−175.34 (12)	C2—C3—C4—N1	179.6 (3)
O2ⁱ—Zn1—O2—Zn1ⁱ	0.0	O5—N1—C4—C3	−2.0 (5)
O8—Zn1—O2—Zn1ⁱ	90.08 (11)	O4—N1—C4—C3	177.5 (3)
O6—Zn1—O2—Zn1ⁱ	−88.96 (12)	O5—N1—C4—C5	177.5 (3)
O2—Zn1—O3—C7	−8.9 (3)	O4—N1—C4—C5	−3.0 (5)
O7—Zn1—O3—C7	175.4 (3)	C3—C4—C5—C6	−0.2 (6)
O2ⁱ—Zn1—O3—C7	−33.9 (7)	N1—C4—C5—C6	−179.7 (3)
O8—Zn1—O3—C7	81.0 (3)	C4—C5—C6—C7	0.2 (6)
O6—Zn1—O3—C7	−97.2 (3)	Zn1—O3—C7—C6	−170.1 (3)
Zn1—O2—C1—O1	−178.2 (3)	Zn1—O3—C7—C2	8.7 (5)
Zn1ⁱ—O2—C1—O1	−1.1 (5)	C5—C6—C7—O3	178.8 (4)
Zn1—O2—C1—C2	3.9 (5)	C5—C6—C7—C2	−0.1 (6)
Zn1ⁱ—O2—C1—C2	−178.9 (2)	C3—C2—C7—O3	−178.8 (3)
O1—C1—C2—C3	−5.5 (5)	C1—C2—C7—O3	0.5 (6)
O2—C1—C2—C3	172.4 (3)	C3—C2—C7—C6	0.0 (5)
O1—C1—C2—C7	175.2 (4)	C1—C2—C7—C6	179.3 (3)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O8—H8B···O3ⁱⁱ	0.84	1.81	2.651 (3)	173
O8—H8A···O5ⁱⁱⁱ	0.85	2.26	3.038 (4)	153
O7—H7A···O8^iv	0.85	2.58	3.023 (4)	114
O7—H7B···O1ⁱ	0.85	1.77	2.596 (4)	163
O6—H6B···O4^v	0.85	1.87	2.696 (4)	164
O6—H6A···O8^vi	0.85	2.30	3.135 (5)	168

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

Experimental details

Crystal data
Chemical formula	[Zn₂(C₇H₃NO₅)₂(H₂O)₆]
M_r	601.04
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	294
a, b, c (Å)	10.858 (3), 13.645 (3), 6.6367 (17)
β (°)	91.887 (4)
V (Å³)	982.7 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.53
Crystal size (mm)	0.26 × 0.10 × 0.08

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2000)
T_min, T_max	0.752, 0.821
No. of measured, independent and observed [I > 2σ(I)] reflections	5435, 2009, 1418
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.088, 1.03
No. of reflections	2009
No. of parameters	154
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.55

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), 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
O8—H8B···O3ⁱ	0.84	1.81	2.651 (3)	172.8
O8—H8A···O5ⁱⁱ	0.85	2.26	3.038 (4)	152.6
O7—H7A···O8ⁱⁱⁱ	0.85	2.58	3.023 (4)	113.7
O7—H7B···O1^iv	0.85	1.77	2.596 (4)	163.4
O6—H6B···O4^v	0.85	1.87	2.696 (4)	164.1
O6—H6A···O8^vi	0.85	2.30	3.135 (5)	168.1

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

Acknowledgements

The authors thank Yanshan University for financial support.

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