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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 5| May 2010| Page o1219
https://doi.org/10.1107/S1600536810015321

5,5-Di­hydroxy­barbituric acid 1,4-dioxane hemisolvate

Thomas Gelbrich,a* Denise Rossia and Ulrich J. Griessera

aInstitute of Pharmacy, University of Innsbruck, Innrain 52, 6020 Innsbruck, Austria
*Correspondence e-mail: thomas.gelbrich@uibk.ac.at

(Received 23 April 2010; accepted 26 April 2010; online 30 April 2010)

The asymmetric unit of the title compound,, C4H4N2O5·0.5C4H8O2, contains one molecule of 5,5-dihydroxybarbituric acid with a nearly planar barbiturate ring and half a molecule of 1,4-dioxane. The geometry of the centrosymmetric dioxane molecule is close to an ideal chair conformation. The crystal structure exhibits a complex three-dimensional hydrogen-bonded network. Barbiturate mol­ecules are connected to one another via N—H⋯O=C, O—H⋯O=C and N—H⋯O(hydr­oxy) inter­actions, while the barbituric acid mol­ecule is linked to dioxane by an O—H⋯O contact.

Related literature

For the crystal structure of unsolvated 5,5-dihydroxy­barbituric acid, see: Singh (1965[Singh, C. (1965). Acta Cryst. 19, 759-767.]); Harrowfield et al. (1989[Harrowfield, J. M., Skelton, B. W., Soudi, A. A. & White, A. H. (1989). Aust. J. Chem. 42, 1795-1798.]). For the related monohydrate, see Lewis & Tocher (2004a[Lewis, T. C. & Tocher, D. A. (2004a). Acta Cryst. E60, o1689-o1690.]). For the related trihydrate, see Mootz & Jeffrey (1965[Mootz, D. & Jeffrey, G. A. (1965). Acta Cryst. 19, 717-725.]); Lewis & Tocher (2004b[Lewis, T. C. & Tocher, D. A. (2004b). Acta Cryst. E60, o1748-o1750.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data

  • C4H4N2O5·0.5C4H8O2

  • Mr = 204.14

  • Triclinic, [P \overline 1]

  • a = 6.0232 (3) Å

  • b = 8.3954 (4) Å

  • c = 8.6858 (5) Å

  • α = 106.007 (4)°

  • β = 94.459 (3)°

  • γ = 110.126 (3)°

  • V = 389.09 (3) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.16 mm−1

  • T = 120 K

  • 0.10 × 0.10 × 0.10 mm
Data collection

  • Bruker-Nonius Roper CCD camera on κ-goniostat diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2007[Sheldrick, G. M. (2007). SADABS. University of Göttingen,Germany.]) Tmin = 0.984, Tmax = 0.984

  • 5726 measured reflections

  • 1529 independent reflections

  • 1198 reflections with I > 2σ(I)

  • Rint = 0.049
Refinement

  • R[F2 > 2σ(F2)] = 0.045

  • wR(F2) = 0.131

  • S = 1.01

  • 1529 reflections

  • 148 parameters

  • 4 restraints

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

  • Δρmax = 0.25 e Å−3

  • Δρmin = −0.29 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1N⋯O6i 0.89 (2) 2.39 (3) 3.068 (2) 134 (3)
N1—H1N⋯O7ii 0.89 (2) 2.44 (2) 3.180 (2) 141 (3)
N3—H3N⋯O2iii 0.88 (2) 1.93 (2) 2.810 (2) 172 (2)
O7—H7O⋯O1S 0.87 (2) 1.87 (2) 2.732 (2) 171 (3)
O8—H8O⋯O4iv 0.83 (2) 1.95 (2) 2.751 (2) 162 (3)
Symmetry codes: (i) -x+2, -y+2, -z+1; (ii) x+1, y, z; (iii) -x+1, -y+1, -z; (iv) -x, -y+1, -z+1.

Data collection: COLLECT (Hooft, 1998[Hooft, R. W. W. (1998). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DENZO (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: XP in SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43. Submitted.]).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810015321/jh2150sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810015321/jh2150Isup2.hkl

checkCIF report


Comment top

The crystal structures of an unsolvated form (Singh, 1965; Harrowfield et al., 1989), a monohydrate (Lewis & Tocher, 2004a) and a trihydrate (Mootz & Jeffrey, 1965; Lewis & Tocher, 2004b) of 5,5-dihydroxybarbituric acid have been reported previously. The asymmetric unit of the title structure consists of one molecule of the barbituric acid derivative and one half of a dioxane moiety (Fig. 1). The six-membered C4N2 ring of the former is essentially planar, and its bond distances and angles are in agreement with the parameters observed for the unsolvated and hydrate forms.

This crystal structure is characterized by extensive hydrogen bonding. Each dihydroxybarbituric acid molecule is linked to two molecules of the same kind via two centrosymmetric N—H···O=C double bridges and a double bridge O—H···O=C connects it to a third molecule. Joining these R22(8) and R22(10) motifs (Bernstein et al., 1995) gives a larger ring of six dihydroxybarbituric acid molecules. Two molecules of each such ring are additionally O—H···O bonded to a dioxane molecule which lies in the centre of the ring. Fig. 2 shows the 2-dimensional H-bonded net parallel to (121) which is obtained from these interactions. Additionally, one NH and one OH group of each dihydroxybarbituric acid molecule are engaged as H-bond donor and acceptor, respectively, in N—H···O(hydroxy) interactions. These particular contacts, indicated by arrows in Fig. 2, connect adjacent H-bonded 2D units of the kind discussed above to one another, and an overall three-dimensional hydrogen bonded network is therefore formed. As expected, the two hydrogen bonds in which the N1—H group is involved exhibit a much less favourable geometry than the single hydrogen bond in which the N3—H group is employed.

Related literature top

For the crystal structure of unsolvated 5,5-dihydroxybarbituric acid, see: Singh (1965); Harrowfield et al. (1989). For the related monohydrate, see Lewis & Tocher (2004a). For the related trihydrate, see Mootz & Jeffrey (1965); Lewis & Tocher (2004b). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

A solution of 5,5-dibromobarbituric acid (Sigma-Aldrich) in dioxane was filled into an NMR tube for a crystallisation experiment by slow evaporation of the solvent. After four months, an amber-coloured syrup had formed, indicating decomposition of the original compound. This liquid contained a large colourless crystal that prooved to be composed of the title compound.

Refinement top

All H atoms were identified in a difference map. H atoms bonded to secondary CH2 (C—H = 0.99 Å) carbon atoms were positioned geometrically, and hydrogen atoms attached to N and O were refined with restrained distances [N—H = 0.88 (2) Å, O—H = 0.82 (2) Å]. The Uiso parameters of all hydrogen atoms were refined freely.

Structure description top

The crystal structures of an unsolvated form (Singh, 1965; Harrowfield et al., 1989), a monohydrate (Lewis & Tocher, 2004a) and a trihydrate (Mootz & Jeffrey, 1965; Lewis & Tocher, 2004b) of 5,5-dihydroxybarbituric acid have been reported previously. The asymmetric unit of the title structure consists of one molecule of the barbituric acid derivative and one half of a dioxane moiety (Fig. 1). The six-membered C4N2 ring of the former is essentially planar, and its bond distances and angles are in agreement with the parameters observed for the unsolvated and hydrate forms.

This crystal structure is characterized by extensive hydrogen bonding. Each dihydroxybarbituric acid molecule is linked to two molecules of the same kind via two centrosymmetric N—H···O=C double bridges and a double bridge O—H···O=C connects it to a third molecule. Joining these R22(8) and R22(10) motifs (Bernstein et al., 1995) gives a larger ring of six dihydroxybarbituric acid molecules. Two molecules of each such ring are additionally O—H···O bonded to a dioxane molecule which lies in the centre of the ring. Fig. 2 shows the 2-dimensional H-bonded net parallel to (121) which is obtained from these interactions. Additionally, one NH and one OH group of each dihydroxybarbituric acid molecule are engaged as H-bond donor and acceptor, respectively, in N—H···O(hydroxy) interactions. These particular contacts, indicated by arrows in Fig. 2, connect adjacent H-bonded 2D units of the kind discussed above to one another, and an overall three-dimensional hydrogen bonded network is therefore formed. As expected, the two hydrogen bonds in which the N1—H group is involved exhibit a much less favourable geometry than the single hydrogen bond in which the N3—H group is employed.

For the crystal structure of unsolvated 5,5-dihydroxybarbituric acid, see: Singh (1965); Harrowfield et al. (1989). For the related monohydrate, see Lewis & Tocher (2004a). For the related trihydrate, see Mootz & Jeffrey (1965); Lewis & Tocher (2004b). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Computing details top

Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); data reduction: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); program(s) used to solve structure: SHELXL97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. The molecular structures of (I) with displacement ellipsoids drawn at the 50% probability level. Hydrogen atoms are shown as spheres of arbitrary size. Symmetry code: (i) -x+1, -y+2, -z+2.
[Figure 2] Fig. 2. Portion of a hydrogen bonded sheet parallel to (1-21) showing N—H···O=C and O—H···O=C bonds between barbituric acid molecules and O—H···O bonds between barbituric acid and dioxane. N—H···O(hydroxy) interactions linking to two adjacent sheets are indicated by arrows. Dioxane H atoms are omitted for clarity.
5,5-dihydroxybarbituric acid 1,4-dioxane hemisolvate top
Crystal data top
C4H4N2O5·0.5C4H8O2Z = 2
Mr = 204.14F(000) = 212
Triclinic, P1Dx = 1.742 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.0232 (3) ÅCell parameters from 3190 reflections
b = 8.3954 (4) Åθ = 2.9–26.0°
c = 8.6858 (5) ŵ = 0.16 mm−1
α = 106.007 (4)°T = 120 K
β = 94.459 (3)°Block, colourless
γ = 110.126 (3)°0.10 × 0.10 × 0.10 mm
V = 389.09 (3) Å3
Data collection top
Bruker-Nonius Roper CCD camera on κ-goniostat
diffractometer		1529 independent reflections
Radiation source: Bruker–Nonius FR591 rotating anode1198 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.049
Detector resolution: 9.091 pixels mm-1θmax = 26.0°, θmin = 3.6°
φ & ω scansh = −7→7
Absorption correction: multi-scan
(SADABS; Sheldrick, 2007)		k = −10→10
Tmin = 0.984, Tmax = 0.984l = −10→10
5726 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.131 w = 1/[σ2(Fo2) + (0.0787P)2 + 0.0767P]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max < 0.001
1529 reflectionsΔρmax = 0.25 e Å−3
148 parametersΔρmin = −0.29 e Å−3
4 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.062 (16)
Crystal data top
C4H4N2O5·0.5C4H8O2γ = 110.126 (3)°
Mr = 204.14V = 389.09 (3) Å3
Triclinic, P1Z = 2
a = 6.0232 (3) ÅMo Kα radiation
b = 8.3954 (4) ŵ = 0.16 mm−1
c = 8.6858 (5) ÅT = 120 K
α = 106.007 (4)°0.10 × 0.10 × 0.10 mm
β = 94.459 (3)°
Data collection top
Bruker-Nonius Roper CCD camera on κ-goniostat
diffractometer		1529 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2007)		1198 reflections with I > 2σ(I)
Tmin = 0.984, Tmax = 0.984Rint = 0.049
5726 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0454 restraints
wR(F2) = 0.131H atoms treated by a mixture of independent and constrained refinement
S = 1.01Δρmax = 0.25 e Å−3
1529 reflectionsΔρmin = −0.29 e Å−3
148 parameters
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
xyzUiso*/Ueq
N10.7757 (3)0.7817 (2)0.3822 (2)0.0204 (4)
H1N0.934 (3)0.835 (4)0.398 (4)0.061 (10)*
N30.4114 (3)0.5803 (2)0.2073 (2)0.0175 (4)
H3N0.342 (4)0.506 (3)0.107 (2)0.029 (6)*
O20.7627 (3)0.65461 (19)0.11484 (17)0.0242 (4)
O40.0683 (3)0.4836 (2)0.29980 (18)0.0264 (4)
O60.8029 (3)0.90452 (19)0.65175 (17)0.0265 (4)
O70.3029 (2)0.83394 (18)0.53542 (18)0.0212 (4)
H7O0.360 (6)0.895 (4)0.638 (2)0.064 (10)*
O80.3738 (3)0.60819 (19)0.60882 (17)0.0221 (4)
H8O0.228 (3)0.574 (4)0.615 (4)0.060 (10)*
C20.6555 (4)0.6706 (3)0.2277 (2)0.0189 (5)
C40.2802 (4)0.5806 (3)0.3280 (2)0.0185 (5)
C60.6801 (3)0.8039 (3)0.5200 (2)0.0186 (5)
C50.4070 (3)0.7064 (3)0.5010 (2)0.0178 (5)
O1S0.4460 (2)1.04067 (18)0.85656 (16)0.0201 (4)
C1S0.6766 (4)1.1366 (3)0.9647 (3)0.0218 (5)
H1S10.67421.24501.04570.030 (6)*
H1S20.80271.17550.90140.013 (5)*
C2S0.2647 (3)0.9800 (3)0.9481 (2)0.0213 (5)
H2S10.10660.91130.87330.031 (6)*
H2S20.25301.08481.02870.036 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0145 (9)0.0210 (9)0.0182 (10)0.0021 (8)0.0036 (7)0.0005 (7)
N30.0161 (9)0.0192 (9)0.0127 (9)0.0042 (7)0.0020 (7)0.0019 (7)
O20.0192 (8)0.0258 (8)0.0188 (8)0.0030 (6)0.0070 (6)−0.0003 (6)
O40.0159 (8)0.0307 (8)0.0211 (8)0.0004 (7)0.0042 (6)0.0016 (6)
O60.0191 (8)0.0319 (9)0.0186 (8)0.0056 (7)0.0014 (6)−0.0007 (6)
O70.0190 (8)0.0229 (8)0.0200 (8)0.0092 (6)0.0031 (6)0.0031 (6)
O80.0214 (8)0.0279 (8)0.0202 (8)0.0096 (7)0.0070 (6)0.0116 (6)
C20.0179 (10)0.0165 (10)0.0187 (11)0.0036 (8)0.0040 (9)0.0039 (8)
C40.0170 (10)0.0187 (10)0.0189 (11)0.0056 (8)0.0042 (8)0.0061 (8)
C60.0166 (10)0.0198 (10)0.0180 (11)0.0060 (8)0.0036 (8)0.0053 (8)
C50.0162 (10)0.0199 (10)0.0182 (11)0.0069 (8)0.0054 (8)0.0068 (8)
O1S0.0158 (7)0.0249 (8)0.0162 (8)0.0054 (6)0.0027 (6)0.0044 (6)
C1S0.0152 (10)0.0225 (10)0.0205 (11)0.0019 (8)−0.0004 (8)0.0039 (8)
C2S0.0138 (10)0.0290 (11)0.0182 (11)0.0059 (9)0.0040 (8)0.0060 (9)
Geometric parameters (Å, º) top
N1—C61.362 (3)O8—H8O0.834 (18)
N1—C21.374 (3)C4—C51.532 (3)
N1—H1N0.886 (18)C6—C51.536 (3)
N3—C41.361 (3)O1S—C2S1.435 (2)
N3—C21.373 (3)O1S—C1S1.439 (2)
N3—H3N0.883 (17)C1S—C2Si1.504 (3)
O2—C21.217 (2)C1S—H1S10.9900
O4—C41.216 (2)C1S—H1S20.9900
O6—C61.214 (2)C2S—C1Si1.504 (3)
O7—C51.394 (2)C2S—H2S10.9900
O7—H7O0.867 (18)C2S—H2S20.9900
O8—C51.392 (2)
C6—N1—C2126.66 (17)O8—C5—C4109.42 (16)
C6—N1—H1N115 (2)O7—C5—C4105.53 (15)
C2—N1—H1N118 (2)O8—C5—C6106.79 (16)
C4—N3—C2125.94 (17)O7—C5—C6108.58 (15)
C4—N3—H3N119.4 (16)C4—C5—C6114.24 (16)
C2—N3—H3N114.2 (16)C2S—O1S—C1S109.37 (15)
C5—O7—H7O105 (2)O1S—C1S—C2Si110.63 (16)
C5—O8—H8O107 (2)O1S—C1S—H1S1109.5
O2—C2—N3122.08 (19)C2Si—C1S—H1S1109.5
O2—C2—N1120.85 (18)O1S—C1S—H1S2109.5
N3—C2—N1117.07 (17)C2Si—C1S—H1S2109.5
O4—C4—N3121.06 (19)H1S1—C1S—H1S2108.1
O4—C4—C5120.76 (18)O1S—C2S—C1Si110.95 (16)
N3—C4—C5118.18 (17)O1S—C2S—H2S1109.4
O6—C6—N1121.57 (18)C1Si—C2S—H2S1109.4
O6—C6—C5120.87 (17)O1S—C2S—H2S2109.4
N1—C6—C5117.43 (17)C1Si—C2S—H2S2109.4
O8—C5—O7112.40 (16)H2S1—C2S—H2S2108.0
C4—N3—C2—O2175.20 (18)N3—C4—C5—O7112.76 (19)
C4—N3—C2—N1−5.1 (3)O4—C4—C5—C6173.36 (17)
C6—N1—C2—O2−176.10 (18)N3—C4—C5—C6−6.4 (2)
C6—N1—C2—N34.2 (3)O6—C6—C5—O8−57.3 (2)
C2—N3—C4—O4−173.22 (18)N1—C6—C5—O8126.73 (18)
C2—N3—C4—C56.6 (3)O6—C6—C5—O764.2 (2)
C2—N1—C6—O6179.18 (18)N1—C6—C5—O7−111.85 (19)
C2—N1—C6—C5−4.8 (3)O6—C6—C5—C4−178.39 (17)
O4—C4—C5—O853.7 (2)N1—C6—C5—C45.6 (2)
N3—C4—C5—O8−126.09 (18)C2S—O1S—C1S—C2Si57.5 (2)
O4—C4—C5—O7−67.4 (2)C1S—O1S—C2S—C1Si−57.7 (2)
Symmetry code: (i) −x+1, −y+2, −z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O6ii0.89 (2)2.39 (3)3.068 (2)134 (3)
N1—H1N···O7iii0.89 (2)2.44 (2)3.180 (2)141 (3)
N3—H3N···O2iv0.88 (2)1.93 (2)2.810 (2)172 (2)
O7—H7O···O1S0.87 (2)1.87 (2)2.732 (2)171 (3)
O8—H8O···O4v0.83 (2)1.95 (2)2.751 (2)162 (3)
Symmetry codes: (ii) −x+2, −y+2, −z+1; (iii) x+1, y, z; (iv) −x+1, −y+1, −z; (v) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formulaC4H4N2O5·0.5C4H8O2
Mr204.14
Crystal system, space groupTriclinic, P1
Temperature (K)120
a, b, c (Å)6.0232 (3), 8.3954 (4), 8.6858 (5)
α, β, γ (°)106.007 (4), 94.459 (3), 110.126 (3)
V (Å3)389.09 (3)
Z2
Radiation typeMo Kα
µ (mm−1)0.16
Crystal size (mm)0.10 × 0.10 × 0.10
Data collection
DiffractometerBruker-Nonius Roper CCD camera on κ-goniostat
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2007)
Tmin, Tmax0.984, 0.984
No. of measured, independent and
observed [I > 2σ(I)] reflections		5726, 1529, 1198
Rint0.049
(sin θ/λ)max (Å−1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.131, 1.01
No. of reflections1529
No. of parameters148
No. of restraints4
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.25, −0.29

Computer programs: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2008), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O6i0.886 (18)2.39 (3)3.068 (2)134 (3)
N1—H1N···O7ii0.886 (18)2.44 (2)3.180 (2)141 (3)
N3—H3N···O2iii0.883 (17)1.933 (18)2.810 (2)172 (2)
O7—H7O···O1S0.867 (18)1.873 (19)2.732 (2)171 (3)
O8—H8O···O4iv0.834 (18)1.95 (2)2.751 (2)162 (3)
Symmetry codes: (i) −x+2, −y+2, −z+1; (ii) x+1, y, z; (iii) −x+1, −y+1, −z; (iv) −x, −y+1, −z+1.
 

Acknowledgements

TG acknowledges financial support from the Lise Meitner Program of the Austrian Science Fund (FWF, project LM 1135-N17).

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ISSN: 2056-9890
Volume 66| Part 5| May 2010| Page o1219
https://doi.org/10.1107/S1600536810015321
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