Poly[tetra­aqua­(μ6-9,10-dioxo-9,10-dihydro­anthracene-1,4,5,8-tetra­carboxyl­ato)dimanganese(II)]

Xu, R.; Liu, J.-L.

doi:10.1107/S1600536812027158

metal-organic compounds

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Volume 68| Part 7| July 2012| Page m957

https://doi.org/10.1107/S1600536812027158

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Poly[tetraaqua(μ₆-9,10-dioxo-9,10-dihydroanthracene-1,4,5,8-tetracarboxylato)dimanganese(II)]

Rui Xu ^a and Jian-Lan Liu ^a ^*

^aDepartment of Applied Chemistry, College of Science, Nanjing University of Technology, Nanjing 210009, People's Republic of China
^*Correspondence e-mail: zsp200109@126.com

(Received 25 May 2012; accepted 15 June 2012; online 20 June 2012)

The title complex, [Mn₂(C₁₈H₄O₁₀)(H₂O)₄]_n, was synthesized from manganese(II) chloride tetrahydrate and 9,10-dioxo-9,10-dihydroanthracene-1,4,5,8-tetracarboxylic acid (H₄AQTC) in water. The anthraquinone unit is located about a crystallographic center of inversion. Each asymmetric unit therefore contains one Mn^II atom, two water ligands and one half AQTC⁴⁻ anion. The Mn^II atom is coordinated in a distorted octahedral geometry by four O atoms from three AQTC⁴⁻ ligands and two water O atoms. Two of the carboxylate groups coordinate one Mn^II atom in a chelating mode, whereas the others each coordinate two Mn^II atoms. Each AQTC⁴⁻ tetra-anion therefore coordinates six different Mn^II ions and, as a result, a three-dimensional coordination polymer is formed. O—H⋯O hydrogen bonds, some of them bifurcated, between water ligands and neighboring water or anthraquinone ligands are observed in the crystal structure.

Related literature

For general background to metal-organic frameworks, see: Li et al. (1999 , 2012 ); Cheng et al. (2010 ); Hong et al. (2009 ); Miller & Gatteschi (2011 ); Liu et al. (2010 ).

Experimental

Crystal data

[Mn₂(C₁₈H₄O₁₀)(H₂O)₄]
M_r = 562.16
Monoclinic, P 2₁ /c
a = 11.2255 (16) Å
b = 8.4153 (13) Å
c = 9.7252 (14) Å
β = 92.355 (2)°
V = 917.9 (2) Å³
Z = 2
Mo Kα radiation
μ = 1.46 mm⁻¹
T = 273 K
0.46 × 0.32 × 0.26 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.553, T_max = 0.702
4340 measured reflections
1609 independent reflections
1499 reflections with I > 2σ(I)
R_int = 0.065

Refinement

R[F² > 2σ(F²)] = 0.028
wR(F²) = 0.076
S = 1.08
1609 reflections
170 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.41 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O8—H3⋯O2ⁱ	0.78 (3)	2.03 (3)	2.775 (2)	160 (3)
O8—H4⋯O3ⁱⁱ	0.89 (4)	1.86 (4)	2.742 (2)	174 (3)
O8—H4⋯O6ⁱⁱ	0.89 (4)	2.60 (3)	3.159 (2)	121 (3)
O9—H5⋯O8ⁱⁱⁱ	0.81 (1)	2.03 (1)	2.832 (3)	168 (4)
O9—H6⋯O6ⁱⁱ	0.81 (1)	2.38 (2)	3.135 (3)	157 (5)
O9—H6⋯O7ⁱⁱⁱ	0.81 (1)	2.50 (4)	3.031 (3)	124 (4)
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[x-1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iii) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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 I, global. DOI: https://doi.org/10.1107/S1600536812027158/im2383sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812027158/im2383Isup2.hkl

checkCIF report

Comment top

Porous solid materials, such as MOFs (metal-organic frameworks) have been widely studied for their potential applications in gas absorption, separation, catalysis and magnetic materials. Explorations of advanced porous materials for these applications are an intense subject of scientific research (Li et al.,1999; Li et al., 2012; Cheng et al., 2010; Hong et al., 2009; Miller & Gatteschi, 2011; Liu et al., 2010.) Herein we report the crystal structure of the title compound.

The molecular structure of (I) is illustrated in Fig. 1., a summary of the observed hydrogen bonds and the corresponding angles are given in Table 1.

Each asymmetric unit therefore contains one manganese(II) atom, two water ligands and one half AQTC^4- ligand. The coordination sphere around manganese is distorted octahedral due to the coordination of four O atoms from three AQTC^4- ligands and two O atoms from two water molecules. Two of the carboxylate groups coordinate one manganese in a chelating mode whereas the others each coordinate two manganese center. Each AQTC^4-therefore coordinates six different manganese ions and as a result a three-dimensional coordination polymer is formed.

Related literature top

For general background to metal-organic frameworks, see: Li et al. (1999, 2012); Cheng et al. (2010); Hong et al. (2009); Miller & Gatteschi (2011); Liu et al. (2010).

Experimental top

A mixture of 9,10-dioxo-9,10-dihydroanthracene-1,4,5,8-tetracarboxylic acid (H₄AQTC; 0.025 mmol, 9.8 mg) was added to distilled water (4 ml) and ultra-sounded for 10 min. The pH value of the mixture was then adjusted to 7.0 with sodium hydroxide (0.5 mol L^-1), prior to the addition of manganese(II) chloride tetrahydrate (0.05 mmol, 9.9 mg). The reactants were placed in a Teflon-lined stainless steel vessel, heated for 3 days, and then cooled to ambient temperature over 12 h. The solution was exposed to air for three days leading to the precipitation of brown crystals (yield 10%).

Structure description top

The molecular structure of (I) is illustrated in Fig. 1., a summary of the observed hydrogen bonds and the corresponding angles are given in Table 1.

For general background to metal-organic frameworks, see: Li et al. (1999, 2012); Cheng et al. (2010); Hong et al. (2009); Miller & Gatteschi (2011); Liu et al. (2010).

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. One repeating unit of the coordination polymer, showing displacement ellipsoids at the 30% probability level. [Symmetry codes: (#1) x + 1,-y,-z + 1; (#2) x + 1,y + 1/2,-z + 1/2; (#3) x + 1,-y + 1,-z + 1; (#4) x + 1,y - 1/2,-z + 1/2.]
	Fig. 2. A view of the crystal structure of the title compound.

Poly[tetraaqua(µ₆-9,10-dioxo-9,10-dihydroanthracene-1,4,5,8- tetracarboxylato)dimanganese(II)] top

Crystal data top

[Mn₂(C₁₈H₄O₁₀)(H₂O)₄]	F(000) = 564
M_r = 562.16	D_x = 2.034 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5133 reflections
a = 11.2255 (16) Å	θ = 2.2–27.6°
b = 8.4153 (13) Å	µ = 1.46 mm⁻¹
c = 9.7252 (14) Å	T = 273 K
β = 92.355 (2)°	Block, brown
V = 917.9 (2) Å³	0.46 × 0.32 × 0.26 mm
Z = 2

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	1609 independent reflections
Radiation source: fine-focus sealed tube	1499 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.065
phi and ω scans	θ_max = 25.0°, θ_min = 3.0°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −12→13
T_min = 0.553, T_max = 0.702	k = −10→7
4340 measured reflections	l = −11→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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.076	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ²(F_o²) + (0.0357P)² + 0.3487P] where P = (F_o² + 2F_c²)/3
1609 reflections	(Δ/σ)_max < 0.001
170 parameters	Δρ_max = 0.35 e Å⁻³
2 restraints	Δρ_min = −0.41 e Å⁻³

Crystal data top

[Mn₂(C₁₈H₄O₁₀)(H₂O)₄]	V = 917.9 (2) Å³
M_r = 562.16	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.2255 (16) Å	µ = 1.46 mm⁻¹
b = 8.4153 (13) Å	T = 273 K
c = 9.7252 (14) Å	0.46 × 0.32 × 0.26 mm
β = 92.355 (2)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	1609 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	1499 reflections with I > 2σ(I)
T_min = 0.553, T_max = 0.702	R_int = 0.065
4340 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	2 restraints
wR(F²) = 0.076	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	Δρ_max = 0.35 e Å⁻³
1609 reflections	Δρ_min = −0.41 e Å⁻³
170 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	0.32095 (18)	0.3515 (2)	0.3203 (2)	0.0199 (4)
C2	0.44180 (17)	0.2999 (2)	0.37593 (19)	0.0182 (4)
C3	0.47029 (17)	0.1544 (2)	0.43842 (19)	0.0174 (4)
C4	0.58569 (16)	0.1290 (2)	0.49497 (19)	0.0168 (4)
C5	0.67291 (17)	0.2464 (2)	0.4857 (2)	0.0176 (4)
C6	0.64515 (18)	0.3863 (2)	0.4181 (2)	0.0214 (4)
H1	0.7036	0.4632	0.4081	0.026*
C7	0.53093 (18)	0.4128 (2)	0.3654 (2)	0.0214 (4)
H2	0.5133	0.5087	0.3217	0.026*
C8	0.79987 (17)	0.2271 (2)	0.5408 (2)	0.0187 (4)
C9	0.38273 (18)	0.0223 (2)	0.4344 (2)	0.0173 (4)
Mn1	0.14215 (3)	0.50978 (3)	0.21336 (3)	0.02054 (15)
O1	0.31881 (13)	0.4118 (2)	0.20209 (15)	0.0305 (4)
O2	0.23044 (12)	0.35278 (18)	0.39148 (15)	0.0261 (4)
O3	0.87242 (12)	0.15778 (18)	0.46563 (15)	0.0245 (3)
O6	0.82943 (13)	0.28802 (18)	0.65405 (15)	0.0274 (4)
O7	0.28972 (13)	0.03344 (17)	0.36714 (16)	0.0244 (4)
O8	0.09489 (15)	0.2961 (2)	0.08600 (17)	0.0267 (4)
O9	−0.04028 (17)	0.5190 (3)	0.2639 (2)	0.0489 (6)
H3	0.143 (3)	0.273 (4)	0.034 (3)	0.053 (10)*
H4	0.024 (3)	0.306 (4)	0.042 (4)	0.068 (10)*
H5	−0.064 (3)	0.590 (3)	0.312 (3)	0.079 (13)*
H6	−0.091 (3)	0.457 (5)	0.239 (5)	0.114 (17)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0197 (10)	0.0151 (10)	0.0247 (11)	−0.0006 (8)	−0.0031 (8)	0.0011 (8)
C2	0.0176 (10)	0.0206 (10)	0.0166 (10)	0.0002 (8)	0.0007 (7)	0.0003 (8)
C3	0.0157 (9)	0.0201 (10)	0.0163 (10)	0.0020 (8)	0.0004 (7)	−0.0001 (8)
C4	0.0171 (9)	0.0186 (10)	0.0147 (10)	0.0016 (8)	−0.0007 (7)	−0.0010 (7)
C5	0.0172 (10)	0.0191 (10)	0.0163 (10)	0.0015 (8)	−0.0002 (7)	−0.0031 (8)
C6	0.0183 (10)	0.0225 (11)	0.0233 (11)	−0.0042 (8)	0.0000 (8)	0.0011 (8)
C7	0.0223 (10)	0.0191 (10)	0.0225 (10)	0.0012 (8)	−0.0008 (8)	0.0042 (8)
C8	0.0177 (10)	0.0154 (10)	0.0228 (11)	−0.0029 (8)	−0.0027 (8)	0.0029 (8)
C9	0.0158 (10)	0.0183 (10)	0.0178 (10)	0.0016 (8)	0.0002 (8)	−0.0015 (8)
Mn1	0.0173 (2)	0.0225 (2)	0.0215 (2)	0.00180 (12)	−0.00320 (14)	−0.00052 (12)
O1	0.0221 (8)	0.0426 (10)	0.0265 (8)	0.0031 (7)	−0.0023 (6)	0.0113 (7)
O2	0.0205 (8)	0.0280 (8)	0.0299 (8)	0.0030 (6)	0.0035 (6)	0.0038 (6)
O3	0.0166 (7)	0.0319 (8)	0.0247 (8)	0.0000 (6)	−0.0016 (6)	−0.0063 (6)
O6	0.0260 (8)	0.0289 (8)	0.0266 (8)	−0.0003 (7)	−0.0069 (6)	−0.0097 (7)
O7	0.0183 (8)	0.0225 (7)	0.0315 (9)	0.0000 (6)	−0.0105 (6)	0.0041 (6)
O8	0.0185 (8)	0.0339 (9)	0.0276 (9)	0.0005 (7)	−0.0007 (7)	−0.0065 (7)
O9	0.0217 (9)	0.0638 (14)	0.0617 (14)	−0.0095 (9)	0.0059 (9)	−0.0353 (11)

Geometric parameters (Å, º) top

C1—O2	1.253 (3)	C8—O3	1.260 (2)
C1—O1	1.256 (2)	C9—O7	1.212 (2)
C1—C2	1.504 (3)	C9—C4ⁱ	1.483 (3)
C2—C7	1.386 (3)	Mn1—O9	2.1270 (19)
C2—C3	1.398 (3)	Mn1—O3ⁱⁱ	2.1412 (15)
C3—C4	1.403 (3)	Mn1—O6ⁱⁱⁱ	2.1508 (15)
C3—C9	1.483 (3)	Mn1—O1	2.1547 (15)
C4—C5	1.396 (3)	Mn1—O8	2.2350 (16)
C4—C9ⁱ	1.483 (3)	Mn1—O2	2.3637 (15)
C5—C6	1.378 (3)	O3—Mn1^iv	2.1412 (15)
C5—C8	1.511 (3)	O6—Mn1ⁱⁱⁱ	2.1508 (15)
C6—C7	1.379 (3)	O8—H3	0.78 (3)
C6—H1	0.9300	O8—H4	0.89 (4)
C7—H2	0.9300	O9—H5	0.812 (10)
C8—O6	1.247 (2)	O9—H6	0.809 (10)

O2—C1—O1	121.11 (18)	C4ⁱ—C9—C3	119.05 (17)
O2—C1—C2	122.96 (18)	O9—Mn1—O3ⁱⁱ	97.16 (8)
O1—C1—C2	115.40 (17)	O9—Mn1—O6ⁱⁱⁱ	87.31 (7)
C7—C2—C3	118.63 (18)	O3ⁱⁱ—Mn1—O6ⁱⁱⁱ	91.81 (6)
C7—C2—C1	114.76 (17)	O9—Mn1—O1	157.30 (8)
C3—C2—C1	126.59 (18)	O3ⁱⁱ—Mn1—O1	102.77 (5)
C2—C3—C4	119.69 (18)	O6ⁱⁱⁱ—Mn1—O1	102.67 (6)
C2—C3—C9	120.34 (17)	O9—Mn1—O8	87.05 (7)
C4—C3—C9	119.75 (18)	O3ⁱⁱ—Mn1—O8	90.52 (6)
C5—C4—C3	120.36 (18)	O6ⁱⁱⁱ—Mn1—O8	174.13 (6)
C5—C4—C9ⁱ	118.84 (17)	O1—Mn1—O8	82.05 (6)
C3—C4—C9ⁱ	120.80 (17)	O9—Mn1—O2	103.28 (8)
C6—C5—C4	119.34 (17)	O3ⁱⁱ—Mn1—O2	159.49 (5)
C6—C5—C8	116.90 (17)	O6ⁱⁱⁱ—Mn1—O2	87.45 (6)
C4—C5—C8	123.71 (17)	O1—Mn1—O2	57.61 (5)
C5—C6—C7	120.24 (19)	O8—Mn1—O2	92.25 (6)
C5—C6—H1	119.9	C1—O1—Mn1	95.23 (12)
C7—C6—H1	119.9	C1—O2—Mn1	85.71 (12)
C6—C7—C2	121.64 (19)	C8—O3—Mn1^iv	135.36 (13)
C6—C7—H2	119.2	C8—O6—Mn1ⁱⁱⁱ	151.88 (14)
C2—C7—H2	119.2	Mn1—O8—H3	114 (2)
O6—C8—O3	123.22 (18)	Mn1—O8—H4	112 (2)
O6—C8—C5	118.82 (17)	H3—O8—H4	110 (3)
O3—C8—C5	117.82 (17)	Mn1—O9—H5	120 (3)
O7—C9—C4ⁱ	120.01 (18)	Mn1—O9—H6	126 (4)
O7—C9—C3	120.77 (18)	H5—O9—H6	114 (5)

O2—C1—C2—C7	−122.6 (2)	C4—C5—C8—O3	84.0 (2)
O1—C1—C2—C7	49.1 (3)	C2—C3—C9—O7	6.4 (3)
O2—C1—C2—C3	55.6 (3)	C4—C3—C9—O7	−168.17 (19)
O1—C1—C2—C3	−132.7 (2)	C2—C3—C9—C4ⁱ	−178.27 (17)
C7—C2—C3—C4	3.3 (3)	C4—C3—C9—C4ⁱ	7.1 (3)
C1—C2—C3—C4	−174.94 (18)	O2—C1—O1—Mn1	6.2 (2)
C7—C2—C3—C9	−171.33 (17)	C2—C1—O1—Mn1	−165.70 (15)
C1—C2—C3—C9	10.5 (3)	O9—Mn1—O1—C1	−39.0 (2)
C2—C3—C4—C5	−1.8 (3)	O3ⁱⁱ—Mn1—O1—C1	170.17 (12)
C9—C3—C4—C5	172.81 (17)	O6ⁱⁱⁱ—Mn1—O1—C1	75.34 (13)
C2—C3—C4—C9ⁱ	178.11 (17)	O8—Mn1—O1—C1	−101.11 (13)
C9—C3—C4—C9ⁱ	−7.3 (3)	O2—Mn1—O1—C1	−3.32 (11)
C3—C4—C5—C6	−1.2 (3)	O1—C1—O2—Mn1	−5.63 (19)
C9ⁱ—C4—C5—C6	178.86 (18)	C2—C1—O2—Mn1	165.63 (18)
C3—C4—C5—C8	−178.52 (18)	O9—Mn1—O2—C1	169.94 (12)
C9ⁱ—C4—C5—C8	1.6 (3)	O3ⁱⁱ—Mn1—O2—C1	−15.1 (2)
C4—C5—C6—C7	2.8 (3)	O6ⁱⁱⁱ—Mn1—O2—C1	−103.43 (12)
C8—C5—C6—C7	−179.76 (18)	O1—Mn1—O2—C1	3.32 (11)
C5—C6—C7—C2	−1.3 (3)	O8—Mn1—O2—C1	82.44 (12)
C3—C2—C7—C6	−1.8 (3)	O6—C8—O3—Mn1^iv	168.36 (14)
C1—C2—C7—C6	176.64 (19)	C5—C8—O3—Mn1^iv	−15.9 (3)
C6—C5—C8—O6	82.5 (2)	O3—C8—O6—Mn1ⁱⁱⁱ	112.0 (3)
C4—C5—C8—O6	−100.1 (2)	C5—C8—O6—Mn1ⁱⁱⁱ	−63.7 (4)
C6—C5—C8—O3	−93.4 (2)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O8—H3···O2^v	0.78 (3)	2.03 (3)	2.775 (2)	160 (3)
O8—H4···O3^vi	0.89 (4)	1.86 (4)	2.742 (2)	174 (3)
O8—H4···O6^vi	0.89 (4)	2.60 (3)	3.159 (2)	121 (3)
O9—H5···O8^vii	0.81 (1)	2.03 (1)	2.832 (3)	168 (4)
O9—H6···O6^vi	0.81 (1)	2.38 (2)	3.135 (3)	157 (5)
O9—H6···O7^vii	0.81 (1)	2.50 (4)	3.031 (3)	124 (4)

Symmetry codes: (v) x, −y+1/2, z−1/2; (vi) x−1, −y+1/2, z−1/2; (vii) −x, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	[Mn₂(C₁₈H₄O₁₀)(H₂O)₄]
M_r	562.16
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	273
a, b, c (Å)	11.2255 (16), 8.4153 (13), 9.7252 (14)
β (°)	92.355 (2)
V (Å³)	917.9 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.46
Crystal size (mm)	0.46 × 0.32 × 0.26

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.553, 0.702
No. of measured, independent and observed [I > 2σ(I)] reflections	4340, 1609, 1499
R_int	0.065
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.076, 1.08
No. of reflections	1609
No. of parameters	170
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.41

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
O8—H3···O2ⁱ	0.78 (3)	2.03 (3)	2.775 (2)	160 (3)
O8—H4···O3ⁱⁱ	0.89 (4)	1.86 (4)	2.742 (2)	174 (3)
O8—H4···O6ⁱⁱ	0.89 (4)	2.60 (3)	3.159 (2)	121 (3)
O9—H5···O8ⁱⁱⁱ	0.812 (10)	2.033 (13)	2.832 (3)	168 (4)
O9—H6···O6ⁱⁱ	0.809 (10)	2.38 (2)	3.135 (3)	157 (5)
O9—H6···O7ⁱⁱⁱ	0.809 (10)	2.50 (4)	3.031 (3)	124 (4)

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

Acknowledgements

The authors thank the Center of Testing and Analysis, Nanjing University, for support.

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