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ISSN: 2056-9890

Bis(melaminium) succinate succinic acid monosolvate dihydrate

aInstitute for Applied Synthetic Chemistry, Vienna University of Technology, Getreidemarkt 9/163, A-1060 Vienna, Austria, and bInstitute for Chemical Technologies and Analytics, Division of Structural Chemistry, Vienna University of Technology, Getreidemarkt 9/164-SC, A-1060 Vienna, Austria
*Correspondence e-mail: mweil@mail.zserv.tuwien.ac.at

(Received 17 July 2012; accepted 20 July 2012; online 25 July 2012)

The asymmetric unit of the solvated title salt, 2C3H7N6+·C4H4O42−·C4H6O4·2H2O, contains one essentially planar melaminium (2,4,6-triamino-1,3,5-triazin-1-ium) cation (r.m.s. deviation of the non-H atoms = 0.0097 Å), one-half of a succinate anion, one-half of a succinic acid solvent mol­ecule and one water molecule of crystallization; full mol­ecules are generated by inversion symmetry. Supra­molecular layers parallel to (12-1) are formed through extensive inter­molecular hydrogen bonding of the types O—H⋯O, N—H⋯N and N—H⋯O between the components.

Related literature

For the use of melaminium salts in polymer science, see: Weinstabl et al. (2001[Weinstabl, A., Binder, W. H., Gruber, H. & Kantner, W. (2001). J. Appl. Polym. Sci. 81, 1654-1661.]). For a list of structurally determined melaminium salts of purely organic carb­oxy­lic acids, see: Froschauer & Weil (2012[Froschauer, B. & Weil, M. (2012). Acta Cryst. E68, o2553-o2554.]).

[Scheme 1]

Experimental

Crystal data
  • 2C3H7N6+·C4H4O42−·C4H6O4·2H2O

  • Mr = 524.48

  • Triclinic, [P \overline 1]

  • a = 7.1193 (7) Å

  • b = 8.1650 (8) Å

  • c = 9.5595 (9) Å

  • α = 88.013 (2)°

  • β = 84.647 (2)°

  • γ = 88.093 (2)°

  • V = 552.68 (9) Å3

  • Z = 1

  • Mo Kα radiation

  • μ = 0.13 mm−1

  • T = 293 K

  • 0.23 × 0.18 × 0.12 mm

Data collection
  • Siemens SMART CCD diffractometer

  • 5533 measured reflections

  • 2719 independent reflections

  • 1545 reflections with I > 2σ(I)

  • Rint = 0.028

Refinement
  • R[F2 > 2σ(F2)] = 0.047

  • wR(F2) = 0.142

  • S = 0.97

  • 2719 reflections

  • 173 parameters

  • 3 restraints

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

  • Δρmax = 0.30 e Å−3

  • Δρmin = −0.26 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N4—H3⋯N2i 0.86 2.10 2.959 (2) 176
N1—H1⋯O1 0.86 2.01 2.844 (2) 164
N5—H4⋯O3ii 0.86 2.13 2.976 (2) 170
N6—H6⋯N3iii 0.86 2.16 3.015 (2) 173
N1—H1⋯O2 0.86 2.50 3.199 (2) 138
N4—H2⋯O3iv 0.86 2.14 2.799 (2) 134
N4—H2⋯O1 0.86 2.56 3.268 (2) 141
N6—H7⋯O2 0.86 1.94 2.782 (2) 166
N5—H5⋯O1Wv 0.86 2.11 2.912 (2) 154
O1W—H1W⋯O4 0.88 (2) 2.35 (2) 3.195 (2) 162 (3)
O1W—H2W⋯O2vi 0.86 (2) 1.89 (2) 2.726 (2) 167 (3)
O4—H12⋯O1iv 1.02 (2) 1.55 (2) 2.5673 (19) 177 (3)
Symmetry codes: (i) -x, -y+2, -z; (ii) x-1, y+1, z; (iii) -x+1, -y+2, -z+1; (iv) -x+1, -y+1, -z; (v) -x, -y+2, -z+1; (vi) x-1, y, z.

Data collection: SMART (Siemens, 1996[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Siemens, 1996[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]) and ATOMS (Dowty, 2006[Dowty, E. (2006). ATOMS. Shape Software, Kingsport, Tennessee, USA.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


Comment top

The potential substitution of melamine through organic melaminium salts for production of melamine urea formaldehyde (MUF) resins (Weinstabl et al., 2001) render the structural investigation of these compounds interesting. A list of already determined structures of purely organic melaminium salts has been compiled recently by Froschauer & Weil (2012).

The pKa values of 4.21 and 5.72 for the first and second deprotonation step of succinic acid (the pKa of the first deprotonation step of melamine is 5.10) led to a doubly deprotonated anion in the title compound, bis-melaminium succinate succinic acid solvate dihydrate, 2(C3H7N6)+.C4H4O4-.C4H6O4.2(H2O). However, besides lattice water, there is also one succinic acid solvent molecule present in the unit cell. The succinic acid molecule and the succinate anion are located with their central C—C bond on inversion centres. As observed for all single protonated melaminium cations, the protonation of melamine takes place at one of the triazine N ring atoms (Fig. 1).

The melaminium cation is essentially planar with a r.m.s. deviation of 0.0097 Å. Likewise, the anion (r.m.s. deviation 0.039 Å) and the succinic acid molecule (r.m.s. deviation 0.060 Å) can be considered as planar. The angles between the least-squares planes of 6.59 (9) ° and 5.76 (12) ° between the anion and the cation and the succinic acid molecule, respectively, lead to the formation of supramolecular layers where cations are arranged in rows alternating with rows of anions, succinic acid solvent and lattice water molecules (Fig. 2). Extensive intermolecular hydrogen bonding of the types O—H···O, N—H···N and N—H···O between the molecular components is present. Details are reported in Table 1. The motif for the hydrogen-bonded assembly of two melaminium cations in such a layer is the same as in the hydrogenmalonate salt and other melaminium salts (Froschauer & Weil, 2012). In the crystal, the supramolecular layers are arranged parallel to (121) (Fig. 3) with an interplanar distance of approximately 3.15 Å.

Related literature top

For the use of melaminium salts in polymer science, see: Weinstabl et al. (2001). For a list of structurally determined melaminium salts of purely organic carboxylic acids, see: Froschauer & Weil (2012).

Experimental top

79.3 mmol melamine was dissolved under refluxing conditions in 200 ml distilled water. The stoichiometric quantity (1:1) of succinic acid was added within five minutes. The mixture was then refluxed for 30 minutes and then cooled to room temperature. The precipitate formed on cooling was separeted by filtration and washed with cold methanol. The crystalline product was then dried in vacuo at 303–313 K. Single crystal growth was accomplished by dissolution of 1 g of the crystalline product under refluxing conditions in an aqueous methanol solution (2:1 v/v) to get a saturated solution. Then the solution was slowly cooled down to room temperature. Suitable crystals were obtained by slow evaporation of the solvents during five days. The crystals were washed with methanol and dried in vacuo at room temperature giving analytical pure samples. CHN analysis (found/calc.): C (32.13/32.10), H (5.50/5.38), N (31.93/32.05). NMR: (solution, DMSO) chemical shift [p.p.m.]: 1H 10.37 (s, 2H), 6.22 (s, 6H), 2.39 (s, 4H); 13C 174.32, 166.43, 29.29.

Refinement top

The proton at the triazine ring of the melaminium cation was clearly discernible from a difference Fourier map (like all other H atoms). For refinement, the H atoms attached to C or N atoms were set in calculated positions and treated as riding on their parent atoms with C—H = 0.97 Å and N—H = 0.86 Å and with Uiso(H) = 1.2Ueq(C,N). The proton of the carboxy group of the succinic acid solvent molecule was refined with a distance restraint O—H = 1.00 (2) Å; H atoms of the water molecule were likewise refined with a distance restraint of O—H = 0.88 (2) Å.

Structure description top

The potential substitution of melamine through organic melaminium salts for production of melamine urea formaldehyde (MUF) resins (Weinstabl et al., 2001) render the structural investigation of these compounds interesting. A list of already determined structures of purely organic melaminium salts has been compiled recently by Froschauer & Weil (2012).

The pKa values of 4.21 and 5.72 for the first and second deprotonation step of succinic acid (the pKa of the first deprotonation step of melamine is 5.10) led to a doubly deprotonated anion in the title compound, bis-melaminium succinate succinic acid solvate dihydrate, 2(C3H7N6)+.C4H4O4-.C4H6O4.2(H2O). However, besides lattice water, there is also one succinic acid solvent molecule present in the unit cell. The succinic acid molecule and the succinate anion are located with their central C—C bond on inversion centres. As observed for all single protonated melaminium cations, the protonation of melamine takes place at one of the triazine N ring atoms (Fig. 1).

The melaminium cation is essentially planar with a r.m.s. deviation of 0.0097 Å. Likewise, the anion (r.m.s. deviation 0.039 Å) and the succinic acid molecule (r.m.s. deviation 0.060 Å) can be considered as planar. The angles between the least-squares planes of 6.59 (9) ° and 5.76 (12) ° between the anion and the cation and the succinic acid molecule, respectively, lead to the formation of supramolecular layers where cations are arranged in rows alternating with rows of anions, succinic acid solvent and lattice water molecules (Fig. 2). Extensive intermolecular hydrogen bonding of the types O—H···O, N—H···N and N—H···O between the molecular components is present. Details are reported in Table 1. The motif for the hydrogen-bonded assembly of two melaminium cations in such a layer is the same as in the hydrogenmalonate salt and other melaminium salts (Froschauer & Weil, 2012). In the crystal, the supramolecular layers are arranged parallel to (121) (Fig. 3) with an interplanar distance of approximately 3.15 Å.

For the use of melaminium salts in polymer science, see: Weinstabl et al. (2001). For a list of structurally determined melaminium salts of purely organic carboxylic acids, see: Froschauer & Weil (2012).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006) and ATOMS (Dowty, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. The molecular components of the title compound drawn with atomic displacement factors at the 90% probability level. H atoms are displayed as spheres with an arbirtary radius. For the centrosymmetric succinate anion and the succinic acid solvent molecule the symmetry-equivalent atoms are not labelled.
[Figure 2] Fig. 2. Supramolecular layer built up through hydrogen bonding interactions (dashed lines) between the molecular components.
[Figure 3] Fig. 3. The assembly of supramolecular layers in the crystal parallel to (121).
Bis(2,4,6-triamino-1,3,5-triazin-1-ium) succinate succinic acid monosolvate dihydrate top
Crystal data top
2C3H7N6+·C4H4O42·C4H6O4·2H2OZ = 1
Mr = 524.48F(000) = 276
Triclinic, P1Dx = 1.576 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.1193 (7) ÅCell parameters from 1570 reflections
b = 8.1650 (8) Åθ = 2.5–28.8°
c = 9.5595 (9) ŵ = 0.13 mm1
α = 88.013 (2)°T = 293 K
β = 84.647 (2)°Parallelepiped, colourless
γ = 88.093 (2)°0.23 × 0.18 × 0.12 mm
V = 552.68 (9) Å3
Data collection top
Siemens SMART CCD
diffractometer
1545 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.028
Graphite monochromatorθmax = 28.3°, θmin = 2.1°
ω scansh = 99
5533 measured reflectionsk = 1010
2719 independent reflectionsl = 1212
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)] = 0.047H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.142 w = 1/[σ2(Fo2) + (0.0791P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.97(Δ/σ)max < 0.001
2719 reflectionsΔρmax = 0.30 e Å3
173 parametersΔρmin = 0.26 e Å3
3 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.010 (4)
Crystal data top
2C3H7N6+·C4H4O42·C4H6O4·2H2Oγ = 88.093 (2)°
Mr = 524.48V = 552.68 (9) Å3
Triclinic, P1Z = 1
a = 7.1193 (7) ÅMo Kα radiation
b = 8.1650 (8) ŵ = 0.13 mm1
c = 9.5595 (9) ÅT = 293 K
α = 88.013 (2)°0.23 × 0.18 × 0.12 mm
β = 84.647 (2)°
Data collection top
Siemens SMART CCD
diffractometer
1545 reflections with I > 2σ(I)
5533 measured reflectionsRint = 0.028
2719 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0473 restraints
wR(F2) = 0.142H atoms treated by a mixture of independent and constrained refinement
S = 0.97Δρmax = 0.30 e Å3
2719 reflectionsΔρmin = 0.26 e Å3
173 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
xyzUiso*/Ueq
N30.3081 (2)1.0330 (2)0.36672 (15)0.0308 (4)
N10.4064 (2)0.8895 (2)0.16163 (15)0.0323 (4)
H10.48940.82790.11600.039*
O10.62741 (19)0.68205 (18)0.02657 (14)0.0385 (4)
O30.6682 (2)0.2996 (2)0.25900 (15)0.0456 (4)
O20.8071 (2)0.6984 (2)0.14806 (15)0.0480 (5)
O40.3997 (2)0.44613 (19)0.26505 (14)0.0431 (4)
C70.5535 (3)0.3930 (3)0.3191 (2)0.0309 (5)
C10.2450 (3)0.9365 (2)0.10469 (19)0.0284 (4)
N20.1121 (2)1.0287 (2)0.17327 (15)0.0305 (4)
C20.1488 (3)1.0729 (2)0.30373 (18)0.0281 (4)
C60.5839 (3)0.4567 (3)0.46117 (19)0.0339 (5)
H6A0.68710.53210.44910.041*
H6B0.62330.36510.52000.041*
N40.2251 (2)0.8874 (2)0.02317 (16)0.0370 (4)
H30.12500.91510.06320.044*
H20.31230.82770.06640.044*
N60.5975 (2)0.8950 (2)0.34112 (18)0.0402 (5)
H60.62260.92420.42280.048*
H70.67780.83560.29090.048*
C30.4365 (3)0.9412 (2)0.29314 (19)0.0301 (5)
C40.7771 (3)0.6435 (2)0.0324 (2)0.0308 (5)
N50.0177 (2)1.1639 (2)0.37353 (17)0.0396 (5)
H50.03471.19590.45610.048*
H40.08481.19120.33650.048*
O1W0.0343 (3)0.6661 (3)0.36216 (18)0.0637 (6)
H1W0.126 (4)0.591 (3)0.353 (3)0.097*
H2W0.024 (4)0.667 (4)0.288 (2)0.097*
H120.385 (4)0.393 (3)0.171 (2)0.097*
C50.9192 (3)0.5292 (3)0.04228 (19)0.0306 (5)
H5A0.97170.58410.12800.037*
H5B0.85430.43410.06900.037*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N30.0277 (9)0.0441 (10)0.0218 (8)0.0109 (8)0.0092 (7)0.0101 (7)
N10.0283 (9)0.0444 (10)0.0248 (8)0.0147 (8)0.0070 (7)0.0131 (7)
O10.0295 (8)0.0537 (10)0.0344 (8)0.0173 (7)0.0150 (6)0.0151 (7)
O30.0392 (9)0.0659 (11)0.0337 (8)0.0230 (8)0.0151 (7)0.0236 (7)
O20.0455 (9)0.0664 (11)0.0351 (8)0.0258 (8)0.0193 (7)0.0285 (8)
O40.0381 (9)0.0635 (11)0.0303 (8)0.0209 (7)0.0178 (6)0.0191 (7)
C70.0278 (10)0.0395 (12)0.0261 (9)0.0081 (9)0.0067 (8)0.0069 (8)
C10.0269 (10)0.0366 (11)0.0222 (9)0.0051 (8)0.0061 (8)0.0061 (8)
N20.0281 (9)0.0428 (10)0.0217 (8)0.0076 (7)0.0085 (7)0.0097 (7)
C20.0250 (10)0.0386 (11)0.0215 (9)0.0063 (8)0.0062 (8)0.0067 (8)
C60.0296 (11)0.0479 (13)0.0257 (10)0.0076 (9)0.0106 (8)0.0085 (9)
N40.0332 (9)0.0548 (12)0.0245 (8)0.0131 (8)0.0107 (7)0.0169 (8)
N60.0330 (10)0.0596 (12)0.0295 (9)0.0231 (9)0.0130 (7)0.0173 (8)
C30.0301 (10)0.0372 (12)0.0243 (9)0.0055 (9)0.0095 (8)0.0070 (8)
C40.0282 (10)0.0357 (11)0.0294 (10)0.0105 (9)0.0083 (8)0.0083 (8)
N50.0322 (9)0.0630 (13)0.0255 (8)0.0174 (9)0.0127 (7)0.0182 (8)
O1W0.0646 (12)0.0902 (15)0.0408 (9)0.0294 (10)0.0287 (8)0.0315 (9)
C50.0299 (10)0.0388 (12)0.0243 (9)0.0108 (9)0.0087 (8)0.0104 (8)
Geometric parameters (Å, º) top
N3—C31.328 (2)C6—H6A0.9700
N3—C21.358 (2)C6—H6B0.9700
N1—C11.356 (2)N4—H30.8600
N1—C31.378 (2)N4—H20.8600
N1—H10.8600N6—C31.313 (2)
O1—C41.277 (2)N6—H60.8600
O3—C71.217 (2)N6—H70.8600
O2—C41.246 (2)C4—C51.500 (3)
O4—C71.309 (2)N5—H50.8600
O4—H121.023 (17)N5—H40.8600
C7—C61.507 (3)O1W—H1W0.882 (17)
C1—N41.321 (2)O1W—H2W0.856 (18)
C1—N21.328 (2)C5—C5ii1.522 (3)
N2—C21.361 (2)C5—H5A0.9700
C2—N51.319 (2)C5—H5B0.9700
C6—C6i1.514 (4)
C3—N3—C2115.93 (15)C1—N4—H2120.0
C1—N1—C3119.48 (16)H3—N4—H2120.0
C1—N1—H1120.3C3—N6—H6120.0
C3—N1—H1120.3C3—N6—H7120.0
C7—O4—H12111.6 (17)H6—N6—H7120.0
O3—C7—O4122.87 (17)N6—C3—N3122.22 (17)
O3—C7—C6121.05 (18)N6—C3—N1116.61 (17)
O4—C7—C6116.07 (17)N3—C3—N1121.17 (17)
N4—C1—N2120.96 (17)O2—C4—O1121.88 (17)
N4—C1—N1117.14 (17)O2—C4—C5120.22 (17)
N2—C1—N1121.90 (16)O1—C4—C5117.90 (16)
C1—N2—C2115.70 (16)C2—N5—H5120.0
N5—C2—N3117.76 (16)C2—N5—H4120.0
N5—C2—N2116.44 (16)H5—N5—H4120.0
N3—C2—N2125.80 (17)H1W—O1W—H2W107 (3)
C7—C6—C6i116.3 (2)C4—C5—C5ii115.00 (19)
C7—C6—H6A108.2C4—C5—H5A108.5
C6i—C6—H6A108.2C5ii—C5—H5A108.5
C7—C6—H6B108.2C4—C5—H5B108.5
C6i—C6—H6B108.2C5ii—C5—H5B108.5
H6A—C6—H6B107.4H5A—C5—H5B107.5
C1—N4—H3120.0
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+2, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H3···N2iii0.862.102.959 (2)176
N1—H1···O10.862.012.844 (2)164
N5—H4···O3iv0.862.132.976 (2)170
N6—H6···N3v0.862.163.015 (2)173
N1—H1···O20.862.503.199 (2)138
N4—H2···O3vi0.862.142.799 (2)134
N4—H2···O10.862.563.268 (2)141
N6—H7···O20.861.942.782 (2)166
N5—H5···O1Wvii0.862.112.912 (2)154
O1W—H1W···O40.88 (2)2.35 (2)3.195 (2)162 (3)
O1W—H2W···O2viii0.86 (2)1.89 (2)2.726 (2)167 (3)
O4—H12···O1vi1.02 (2)1.55 (2)2.5673 (19)177 (3)
Symmetry codes: (iii) x, y+2, z; (iv) x1, y+1, z; (v) x+1, y+2, z+1; (vi) x+1, y+1, z; (vii) x, y+2, z+1; (viii) x1, y, z.

Experimental details

Crystal data
Chemical formula2C3H7N6+·C4H4O42·C4H6O4·2H2O
Mr524.48
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)7.1193 (7), 8.1650 (8), 9.5595 (9)
α, β, γ (°)88.013 (2), 84.647 (2), 88.093 (2)
V3)552.68 (9)
Z1
Radiation typeMo Kα
µ (mm1)0.13
Crystal size (mm)0.23 × 0.18 × 0.12
Data collection
DiffractometerSiemens SMART CCD
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
5533, 2719, 1545
Rint0.028
(sin θ/λ)max1)0.667
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.142, 0.97
No. of reflections2719
No. of parameters173
No. of restraints3
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.30, 0.26

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2006) and ATOMS (Dowty, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H3···N2i0.862.102.959 (2)175.7
N1—H1···O10.862.012.844 (2)164.2
N5—H4···O3ii0.862.132.976 (2)170.0
N6—H6···N3iii0.862.163.015 (2)173.2
N1—H1···O20.862.503.199 (2)138.4
N4—H2···O3iv0.862.142.799 (2)133.5
N4—H2···O10.862.563.268 (2)140.6
N6—H7···O20.861.942.782 (2)165.6
N5—H5···O1Wv0.862.112.912 (2)154.1
O1W—H1W···O40.882 (17)2.35 (2)3.195 (2)162 (3)
O1W—H2W···O2vi0.856 (18)1.886 (19)2.726 (2)167 (3)
O4—H12···O1iv1.023 (17)1.545 (18)2.5673 (19)177 (3)
Symmetry codes: (i) x, y+2, z; (ii) x1, y+1, z; (iii) x+1, y+2, z+1; (iv) x+1, y+1, z; (v) x, y+2, z+1; (vi) x1, y, z.
 

Acknowledgements

The X-ray centre of the Vienna University of Technology is acknowledged for financial support and for providing access to the single-crystal diffractometer.

References

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First citationFroschauer, B. & Weil, M. (2012). Acta Cryst. E68, o2553–o2554.  CSD CrossRef CAS IUCr Journals Google Scholar
First citationMacrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSiemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.  Google Scholar
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First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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