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ISSN: 2056-9890

Bis(imidazolium) galacta­rate dihydrate

aFaculty of Science and Technology, Queensland University of Technology, GPO Box 2434, Brisbane, Queensland 4001, Australia
*Correspondence e-mail: g.smith@qut.edu.au

(Received 19 August 2010; accepted 19 August 2010; online 25 August 2010)

In the structure of the title salt, 2C3H5N2+·C6H8O82−·2H2O, the galacta­rate dianions have crystallographic inversion symmetry and together with the water mol­ecules of solvation form hydrogen-bonded sheet substructures which extend along (110). The imidazolium cations link these sheets peripherally down c through carboxyl­ate O—H—N and N′—H⋯Ohy­droxy bridges, giving a three-dimensional framework structure.

Related literature

For mention of mucic acid in the Merck Index, see: O'Neil (2001[O'Neil, M. J. (2001). The Merck Index, 13th ed., p. 769. Whitehouse Station, New Jersey: Merck & Co.]). For the structures of imidazolium hydrogen salts of aliphatic dicarb­oxy­lic acids, see: James & Matsushima (1976[James, M. N. G. & Matsushima, M. (1976). Acta Cryst. B32, 1708-1713.]); MacDonald et al. (2001[MacDonald, J. C., Dorrestein, P. C. & Pilley, M. M. (2001). Cryst. Growth Des. 1, 29-35.]); Aakeröy & Hitchcock (1993[Aakeröy, C. B. & Hitchcock, P. B. (1993). Chem. Mater. 3, 1129-1135.]); Fuller et al. (1995[Fuller, J., Carlin, R. T., Simpson, L. J. & Furtak, T. E. (1995). Chem. Mater. 7, 909-919.]); Fukunaga & Ishida (2003[Fukunaga, T. & Ishida, H. (2003). Acta Cryst. E59, o1869-o1871.]); Trivedi et al. (2003[Trivedi, D. R., Ballabh, A. & Dastidar, P. (2003). CrystEngComm, 5, 358-367.]). For the structures of galacta­ric acid, ammonium H galacta­rate, diammonium galacta­rate and copper(II) galacta­rate dihydrate, see: Jeffrey & Wood (1982[Jeffrey, G. A. & Wood, R. A. (1982). Carbohydr. Res. 18, 205-211.]), Bontchev & Moore (2005[Bontchev, R. P. & Moore, R. C. (2005). Carbohydr. Res. 340, 2195-2200.]), Benetollo et al. (1993[Benetollo, F., Bombieri, G., Liang, H., Liao, H., Shi, N. & Wu, J. (1993). J. Crystallogr. Spectrosc. Res. 23, 171-175.]) and Ferrier et al. (1998[Ferrier, F., Avezou, A., Terzian, G. & Benlian, D. (1998). J. Mol. Struct. 442, 281-284.]) respectively. For graph-set analysis, see: Etter et al. (1990[Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.]).

[Scheme 1]

Experimental

Crystal data
  • 2C3H5N2+·C6H8O82−·2H2O

  • Mr = 382.34

  • Triclinic, [P \overline 1]

  • a = 6.9184 (4) Å

  • b = 7.1336 (4) Å

  • c = 9.3652 (5) Å

  • α = 92.000 (5)°

  • β = 100.559 (5)°

  • γ = 109.835 (6)°

  • V = 425.06 (5) Å3

  • Z = 1

  • Mo Kα radiation

  • μ = 0.13 mm−1

  • T = 200 K

  • 0.45 × 0.45 × 0.30 mm

Data collection
  • Oxford Diffraction Gemini-S CCD-detector diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]) Tmin = 0.965, Tmax = 0.980

  • 4949 measured reflections

  • 1657 independent reflections

  • 1431 reflections with I > 2σ(I)

  • Rint = 0.019

Refinement
  • R[F2 > 2σ(F2)] = 0.030

  • wR(F2) = 0.082

  • S = 1.13

  • 1657 reflections

  • 142 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.30 e Å−3

  • Δρmin = −0.20 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N11—H11⋯O21 0.89 (2) 1.84 (2) 2.7311 (15) 175.9 (19)
N31—H31⋯O12i 0.890 (18) 1.795 (19) 2.6810 (14) 174 (2)
O21—H22⋯O1W 0.87 (2) 1.76 (2) 2.6324 (15) 177 (2)
O31—H32⋯O12ii 0.83 (2) 1.89 (2) 2.7104 (13) 170.9 (16)
O1W—H11W⋯O11iii 0.87 (3) 1.82 (3) 2.6799 (14) 170.9 (18)
O1W—H12W⋯O31iv 0.86 (3) 1.94 (3) 2.7763 (15) 164.4 (19)
Symmetry codes: (i) x, y, z-1; (ii) -x+1, -y, -z+2; (iii) x, y+1, z; (iv) x-1, y, z.

Data collection: CrysAlis PRO (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1994[Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) within WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: PLATON.

Supporting information


Comment top

Galactaric acid (mucic acid) (O'Neil, 2001) is the C6 homologue of tartaric acid but differs from it in being achiral and as well has only a small number of representative crystal structures in the CSD, e.g. the acid itself (Jeffrey & Wood, 1982), ammonium hydrogen galactarate (Bontchev & Moore, 2005), diammonium galactarate (Benetollo et al., 1993) and some metal complexes, e.g. copper(II) galactarate dihydrate (a fungicide) (Ferrier et al., 1998). Because the imidazolium cation has proved to be an excellent linking molecule for the generation of supramolecular layered structures particularly with dicarboxylic acids, including hydroxy acids (James & Matsushima, 1976; MacDonald et al., 2001; Aakeröy & Hitchcock, 1993; Fuller et al., 1995; Fukunaga & Ishida, 2003; Trivedi et al., 2003), we carried out a 1:2 stoichiometric reaction of galactaric acid with imidazole in aqueous ethanol and obtained large relatively hard, chemically stable crystals of the title compound, 2(CH6N3+) C6H8O82-. 2H2O (I), and the structure is reported here.

In the structure of (I) (Fig. 1), the galactarate anions lie across crystallographic inversion centres which is also the case in the structure of the parent acid (Jeffrey & Wood, 1982). Hydrogen-bonded anion-water sheets extending across the <100> planes in the unit cell (Fig. 2) are formed through hydroxyl O31–H···O12iiicarboxyl and water-bridging O31···O11ivcarboxyl interactions (for symmetry codes, see Table 1). These include R22(12) and R33(12) cyclic motifs (Etter et al., 1990). The layered substructures are linked peripherally down the c cell direction by the imidazolium cations through carboxyl O···HN,N'—H···O`hydroxyl bridges giving a three-dimensional framework structure (Fig. 3). The structure of (I) differs from those of the anhydrous 1:1 salts of the hydrogen dicarboxylates (MacDonald et al., 2001) in which the bridging imidazolium cations are incorporated within two-dimensional layered structures.

Related literature top

For mention of mucic acid in the Merck Index, see: O'Neil (2001). For the structures of imidazolium hydrogen salts of aliphatic dicarboxylic acids, see: James & Matsushima (1976); MacDonald et al. (2001); Aakeröy & Hitchcock (1993); Fuller et al. (1995); Fukunaga & Ishida (2003); Trivedi et al. (2003). For the structures of galactaric acid, ammonium H galactarate, diammonium galactarate and copper(II) galactarate dihydrate, see: Jeffrey & Wood (1982), Bontchev & Moore (2005), Benetollo et al. (1993) and Ferrier et al. (1998) respectively. For graph-set analysis, see: Etter et al. (1990).

Experimental top

The title compound was synthesized by heating together under reflux for 10 minutes 1 mmol of galactaric acid (mucic acid) and 2 mmol of imidazole in 50 ml of 50% ethanol-water. After concentration to ca 30 ml, partial room temperature evaporation of the hot-filtered solution gave large colourless plates of (I) (m.p. 435 K) from which a suitable analytical specimen was cleaved.

Refinement top

Hydrogen atoms potentially involved in hydrogen-bonding interactions were located by difference methods and their positional and isotropic displacement parameters were refined. Other H atoms were included in the refinement in calculated positions (C–Haromatic = 0.95 Å and others = 1.00 Å) and allowed to ride, with Uiso(H) = 1.2Ueq(C).

Structure description top

Galactaric acid (mucic acid) (O'Neil, 2001) is the C6 homologue of tartaric acid but differs from it in being achiral and as well has only a small number of representative crystal structures in the CSD, e.g. the acid itself (Jeffrey & Wood, 1982), ammonium hydrogen galactarate (Bontchev & Moore, 2005), diammonium galactarate (Benetollo et al., 1993) and some metal complexes, e.g. copper(II) galactarate dihydrate (a fungicide) (Ferrier et al., 1998). Because the imidazolium cation has proved to be an excellent linking molecule for the generation of supramolecular layered structures particularly with dicarboxylic acids, including hydroxy acids (James & Matsushima, 1976; MacDonald et al., 2001; Aakeröy & Hitchcock, 1993; Fuller et al., 1995; Fukunaga & Ishida, 2003; Trivedi et al., 2003), we carried out a 1:2 stoichiometric reaction of galactaric acid with imidazole in aqueous ethanol and obtained large relatively hard, chemically stable crystals of the title compound, 2(CH6N3+) C6H8O82-. 2H2O (I), and the structure is reported here.

In the structure of (I) (Fig. 1), the galactarate anions lie across crystallographic inversion centres which is also the case in the structure of the parent acid (Jeffrey & Wood, 1982). Hydrogen-bonded anion-water sheets extending across the <100> planes in the unit cell (Fig. 2) are formed through hydroxyl O31–H···O12iiicarboxyl and water-bridging O31···O11ivcarboxyl interactions (for symmetry codes, see Table 1). These include R22(12) and R33(12) cyclic motifs (Etter et al., 1990). The layered substructures are linked peripherally down the c cell direction by the imidazolium cations through carboxyl O···HN,N'—H···O`hydroxyl bridges giving a three-dimensional framework structure (Fig. 3). The structure of (I) differs from those of the anhydrous 1:1 salts of the hydrogen dicarboxylates (MacDonald et al., 2001) in which the bridging imidazolium cations are incorporated within two-dimensional layered structures.

For mention of mucic acid in the Merck Index, see: O'Neil (2001). For the structures of imidazolium hydrogen salts of aliphatic dicarboxylic acids, see: James & Matsushima (1976); MacDonald et al. (2001); Aakeröy & Hitchcock (1993); Fuller et al. (1995); Fukunaga & Ishida (2003); Trivedi et al. (2003). For the structures of galactaric acid, ammonium H galactarate, diammonium galactarate and copper(II) galactarate dihydrate, see: Jeffrey & Wood (1982), Bontchev & Moore (2005), Benetollo et al. (1993) and Ferrier et al. (1998) respectively. For graph-set analysis, see: Etter et al. (1990).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) within WinGX (Farrugia, 1999); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular configuration and atom-numbering scheme for the cation, dianion and water species in (I). The galactarate dianion has inversion symmetry [symmetry code: (i) -x + 1, -y + 1, -z + 2]. Non-H atoms are shown as 50% probability ellipsoids and inter-species hydrogen bonds are shown as dashed lines.
[Figure 2] Fig. 2. Hydrogen-bonded anion-water sheet substructures in (I), extending across (110) (imidazolium cations are omitted). For symmetry codes, see Table 1. Hydrogen bonds are shown as dashed lines.
[Figure 3] Fig. 3. The three-dimensional structure of (I) viewed down the approximate a cell direction, showing the imidazolium bridges.
Bis(imidazolium) galactarate dihydrate top
Crystal data top
2C3H5N2+·C6H8O82·2H2OZ = 1
Mr = 382.34F(000) = 202
Triclinic, P1Dx = 1.494 Mg m3
Hall symbol: -P 1Melting point: 435 K
a = 6.9184 (4) ÅMo Kα radiation, λ = 0.71073 Å
b = 7.1336 (4) ÅCell parameters from 3387 reflections
c = 9.3652 (5) Åθ = 3.5–28.7°
α = 92.000 (5)°µ = 0.13 mm1
β = 100.559 (5)°T = 200 K
γ = 109.835 (6)°Plate, colourless
V = 425.06 (5) Å30.45 × 0.45 × 0.30 mm
Data collection top
Oxford Diffraction Gemini-S CCD-detector
diffractometer
1657 independent reflections
Radiation source: Enhance (Mo) X-ray source1431 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.019
ω scansθmax = 26.0°, θmin = 3.5°
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2010)
h = 88
Tmin = 0.965, Tmax = 0.980k = 88
4949 measured reflectionsl = 1111
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.030Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.082H atoms treated by a mixture of independent and constrained refinement
S = 1.13 w = 1/[σ2(Fo2) + (0.0444P)2 + 0.0516P]
where P = (Fo2 + 2Fc2)/3
1657 reflections(Δ/σ)max = 0.001
142 parametersΔρmax = 0.30 e Å3
0 restraintsΔρmin = 0.20 e Å3
Crystal data top
2C3H5N2+·C6H8O82·2H2Oγ = 109.835 (6)°
Mr = 382.34V = 425.06 (5) Å3
Triclinic, P1Z = 1
a = 6.9184 (4) ÅMo Kα radiation
b = 7.1336 (4) ŵ = 0.13 mm1
c = 9.3652 (5) ÅT = 200 K
α = 92.000 (5)°0.45 × 0.45 × 0.30 mm
β = 100.559 (5)°
Data collection top
Oxford Diffraction Gemini-S CCD-detector
diffractometer
1657 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2010)
1431 reflections with I > 2σ(I)
Tmin = 0.965, Tmax = 0.980Rint = 0.019
4949 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0300 restraints
wR(F2) = 0.082H atoms treated by a mixture of independent and constrained refinement
S = 1.13Δρmax = 0.30 e Å3
1657 reflectionsΔρmin = 0.20 e Å3
142 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
xyzUiso*/Ueq
O110.18384 (15)0.07229 (13)0.80626 (9)0.0234 (3)
O120.26773 (14)0.02982 (13)1.04961 (9)0.0207 (3)
O210.19607 (14)0.29951 (14)0.78260 (9)0.0203 (3)
O310.62559 (14)0.35914 (13)0.90945 (10)0.0197 (3)
C10.23436 (18)0.03283 (17)0.92558 (13)0.0154 (3)
C20.25848 (18)0.25478 (17)0.92684 (12)0.0151 (3)
C30.48566 (18)0.38863 (17)0.99549 (13)0.0153 (3)
N110.34766 (19)0.22454 (18)0.54570 (12)0.0261 (4)
N310.35478 (19)0.13600 (18)0.32587 (12)0.0265 (4)
C210.2302 (2)0.1404 (2)0.41585 (14)0.0269 (4)
C410.5588 (2)0.2202 (2)0.40018 (15)0.0302 (5)
C510.5544 (2)0.2764 (2)0.53780 (15)0.0285 (4)
O1W0.02769 (16)0.53271 (15)0.78655 (11)0.0244 (3)
H220.118 (3)0.373 (3)0.7852 (19)0.046 (5)*
H20.163800.280500.987800.0180*
H30.524500.352001.096100.0180*
H320.657 (3)0.260 (3)0.9315 (18)0.040 (5)*
H110.301 (3)0.245 (3)0.625 (2)0.048 (5)*
H210.081000.091500.391600.0320*
H310.318 (3)0.084 (3)0.233 (2)0.044 (5)*
H410.680700.236100.361800.0360*
H510.672400.340100.614800.0340*
H11W0.043 (3)0.660 (4)0.803 (2)0.057 (6)*
H12W0.127 (4)0.500 (3)0.835 (2)0.059 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O110.0320 (5)0.0168 (5)0.0185 (5)0.0058 (4)0.0047 (4)0.0032 (4)
O120.0290 (5)0.0158 (5)0.0174 (4)0.0077 (4)0.0056 (4)0.0024 (3)
O210.0257 (5)0.0230 (5)0.0157 (5)0.0135 (4)0.0032 (4)0.0023 (4)
O310.0214 (5)0.0149 (5)0.0265 (5)0.0079 (4)0.0113 (4)0.0032 (4)
C10.0129 (6)0.0148 (6)0.0174 (6)0.0026 (5)0.0051 (4)0.0001 (5)
C20.0185 (6)0.0143 (6)0.0132 (6)0.0058 (5)0.0049 (5)0.0009 (5)
C30.0185 (6)0.0136 (6)0.0144 (6)0.0052 (5)0.0054 (5)0.0017 (5)
N110.0347 (7)0.0308 (7)0.0175 (6)0.0160 (5)0.0084 (5)0.0031 (5)
N310.0379 (7)0.0260 (6)0.0152 (6)0.0116 (5)0.0044 (5)0.0010 (5)
C210.0273 (7)0.0304 (8)0.0230 (7)0.0104 (6)0.0043 (6)0.0070 (6)
C410.0311 (8)0.0336 (8)0.0301 (8)0.0134 (6)0.0120 (6)0.0064 (6)
C510.0286 (7)0.0294 (8)0.0241 (7)0.0085 (6)0.0007 (6)0.0004 (6)
O1W0.0231 (5)0.0180 (5)0.0325 (6)0.0063 (4)0.0095 (4)0.0005 (4)
Geometric parameters (Å, º) top
O11—C11.2465 (15)N11—H110.89 (2)
O12—C11.2690 (15)N31—H310.890 (18)
O21—C21.4223 (14)C1—C21.5341 (16)
O31—C31.4293 (16)C2—C31.5375 (18)
O21—H220.87 (2)C3—C3i1.5303 (16)
O31—H320.83 (2)C2—H21.0000
O1W—H11W0.87 (3)C3—H31.0000
O1W—H12W0.86 (3)C41—C511.345 (2)
N11—C211.3249 (17)C21—H210.9500
N11—C511.367 (2)C41—H410.9500
N31—C211.3178 (19)C51—H510.9500
N31—C411.369 (2)
C2—O21—H22108.6 (11)O31—C3—C3i107.52 (10)
C3—O31—H32110.6 (13)O21—C2—H2108.00
H11W—O1W—H12W111 (2)C3—C2—H2108.00
C21—N11—C51108.65 (12)C1—C2—H2108.00
C21—N31—C41108.66 (11)O31—C3—H3109.00
C51—N11—H11125.3 (14)C2—C3—H3109.00
C21—N11—H11126.1 (14)C3i—C3—H3109.00
C41—N31—H31123.6 (14)N11—C21—N31108.63 (13)
C21—N31—H31127.7 (14)N31—C41—C51107.15 (13)
O12—C1—C2116.02 (10)N11—C51—C41106.92 (12)
O11—C1—O12124.82 (11)N31—C21—H21126.00
O11—C1—C2119.16 (10)N11—C21—H21126.00
O21—C2—C3111.32 (10)N31—C41—H41126.00
O21—C2—C1110.05 (9)C51—C41—H41126.00
C1—C2—C3110.45 (10)N11—C51—H51127.00
O31—C3—C2109.98 (9)C41—C51—H51127.00
C2—C3—C3i112.11 (10)
C21—N11—C51—C410.42 (16)C1—C2—C3—C3i177.68 (10)
C51—N11—C21—N310.31 (16)C1—C2—C3—O3162.76 (12)
C21—N31—C41—C510.19 (16)O21—C2—C3—C3i59.76 (13)
C41—N31—C21—N110.08 (16)O31—C3—C3i—O31i179.98 (12)
O11—C1—C2—O215.67 (17)C2—C3—C3i—O31i59.01 (12)
O12—C1—C2—O21174.06 (11)C2—C3—C3i—C2i179.98 (12)
O12—C1—C2—C362.63 (14)O31—C3—C3i—C2i59.01 (12)
O11—C1—C2—C3117.63 (13)N31—C41—C51—N110.36 (16)
O21—C2—C3—O3159.81 (13)
Symmetry code: (i) x+1, y+1, z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N11—H11···O210.89 (2)1.84 (2)2.7311 (15)175.9 (19)
N31—H31···O12ii0.890 (18)1.795 (19)2.6810 (14)174 (2)
O21—H22···O1W0.87 (2)1.76 (2)2.6324 (15)177 (2)
O31—H32···O12iii0.83 (2)1.89 (2)2.7104 (13)170.9 (16)
O1W—H11W···O11iv0.87 (3)1.82 (3)2.6799 (14)170.9 (18)
O1W—H12W···O31v0.86 (3)1.94 (3)2.7763 (15)164.4 (19)
C21—H21···O11vi0.952.323.0935 (17)138
C41—H41···O11vii0.952.423.2273 (18)142
C51—H51···O1Wviii0.952.343.2827 (18)173
Symmetry codes: (ii) x, y, z1; (iii) x+1, y, z+2; (iv) x, y+1, z; (v) x1, y, z; (vi) x, y, z+1; (vii) x+1, y, z+1; (viii) x+1, y, z.

Experimental details

Crystal data
Chemical formula2C3H5N2+·C6H8O82·2H2O
Mr382.34
Crystal system, space groupTriclinic, P1
Temperature (K)200
a, b, c (Å)6.9184 (4), 7.1336 (4), 9.3652 (5)
α, β, γ (°)92.000 (5), 100.559 (5), 109.835 (6)
V3)425.06 (5)
Z1
Radiation typeMo Kα
µ (mm1)0.13
Crystal size (mm)0.45 × 0.45 × 0.30
Data collection
DiffractometerOxford Diffraction Gemini-S CCD-detector
Absorption correctionMulti-scan
(CrysAlis PRO; Oxford Diffraction, 2010)
Tmin, Tmax0.965, 0.980
No. of measured, independent and
observed [I > 2σ(I)] reflections
4949, 1657, 1431
Rint0.019
(sin θ/λ)max1)0.616
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.030, 0.082, 1.13
No. of reflections1657
No. of parameters142
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.30, 0.20

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 2008) within WinGX (Farrugia, 1999), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N11—H11···O210.89 (2)1.84 (2)2.7311 (15)175.9 (19)
N31—H31···O12i0.890 (18)1.795 (19)2.6810 (14)174 (2)
O21—H22···O1W0.87 (2)1.76 (2)2.6324 (15)177 (2)
O31—H32···O12ii0.83 (2)1.89 (2)2.7104 (13)170.9 (16)
O1W—H11W···O11iii0.87 (3)1.82 (3)2.6799 (14)170.9 (18)
O1W—H12W···O31iv0.86 (3)1.94 (3)2.7763 (15)164.4 (19)
Symmetry codes: (i) x, y, z1; (ii) x+1, y, z+2; (iii) x, y+1, z; (iv) x1, y, z.
 

Acknowledgements

The authors acknowledge financial support from the Australian Research Committee and the Faculty of Science and Technology, Queensland University of Technology.

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