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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 69| Part 11| November 2013| Pages o1674-o1675
doi:10.1107/S1600536813028250

Bis(2,4,6-tri­amino-1,3,5-triazin-1-ium) 2-[bis­­(carboxyl­atometh­yl)aza­nium­yl]acetate trihydrate

Kreshnik Hoxhaa and Timothy J. Priora*

aDepartment of Chemistry, University of Hull, Kingston upon Hull HU6 7RX, England
*Correspondence e-mail: t.prior@hull.ac.uk

(Received 27 August 2013; accepted 14 October 2013; online 19 October 2013)

The title compound, 2C3H7N6+·C6H7NO62−·3H2O, was obtained by mixing melamine and nitrilo­tri­acetic acid in aqueous solution. There is proton transfer from the nitrilo­triacteic acid to melamine to produce two melaminium cations and an inter­nal proton transfer to generate the [HN(CH2COO)]2− zwitterion. The melaminium cations are arranged in hydrogen-bonded tapes formed by N—H⋯N inter­actions. These tapes extend parallel to the [010] direction and are stacked parallel to the a axis at a mean separation of 3.3559 (11) Å. Between these tapes lie the anions and lattice water mol­ecules. Further O—H⋯O and N—H⋯O hydrogen bonds exist between the water mol­ecules, the anions, and the melaminium cations, generating a three-dimensional array. The crystal examined was found to be twinned by a twofold rotation about the direct lattice direction [100]. The two twin components were present in the ratio 0.5918:0.4082 (14).

CCDC reference: 966425

Related literature

For compounds of melamine with simple carb­oxy­lic acid, see, for example: Froschauer & Weil (2012[Froschauer, B. & Weil, M. (2012). Acta Cryst. E68, o2553-o2554.]); Eppel & Bernstein (2009[Eppel, S. & Bernstein, J. (2009). Cryst. Growth Des. 9, 1683-1691.]); Perpétuo & Janczak (2002[Perpétuo, G. J. & Janczak, J. (2002). Acta Cryst. C58, o112-o114.]). For those with tri­carb­oxy­lic acids, see: Eshtiagh-Hosseini et al. (2010[Eshtiagh-Hosseini, H., Mahjobbizadeh, M., Mirzaei, M., Fromm, K. & Crochet, A. (2010). Eur. J. Chem. 1, 179-181.]); Huczynski et al. (2009[Huczynski, A., Janczak, J. & Brzezinski, B. (2009). J. Mol. Struct. 922, 77-82.]); Perpetuo & Janczak (2003[Perpetuo, G. J. & Janczak, J. (2003). Pol. J. Chem. 77, 1323-1328.]). For assignment of protonation on the grounds of bond angle and bond length, see: Childs et al. (2007[Childs, S. L., Stahly, G. P. & Park, A. (2007). Mol. Pharm. 4, 323-338.]) and Hingerty et al. (1981[Hingerty, B. E., Einstein, J. R. & Wei, C. H. (1981). Acta Cryst. B37, 140-147.]), respectively. An introduction to graph-set theory may be found in Etter et al. (1990[Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.]).

[Scheme 1]

Experimental

Crystal data

  • 2C3H7N6+·C6H7NO62−·3H2O

  • Mr = 497.43

  • Triclinic, [P \overline 1]

  • a = 6.7117 (11) Å

  • b = 12.1495 (19) Å

  • c = 13.102 (3) Å

  • α = 82.714 (15)°

  • β = 89.252 (16)°

  • γ = 83.238 (13)°

  • V = 1052.4 (3) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.13 mm−1

  • T = 150 K

  • 0.36 × 0.16 × 0.04 mm
Data collection

  • Stoe IPDS2 diffractometer

  • Absorption correction: analytical (X-RED and X-SHAPE; Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA, X-RED and X-SHAPE. Stoe & Cie, Darmstadt, Germany.]) Tmin = 0.957, Tmax = 0.994

  • 10946 measured reflections

  • 10946 independent reflections

  • 5515 reflections with I > 2σ(I)
Refinement

  • R[F2 > 2σ(F2)] = 0.084

  • wR(F2) = 0.244

  • S = 0.95

  • 10946 reflections

  • 327 parameters

  • 10 restraints

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

  • Δρmax = 0.40 e Å−3

  • Δρmin = −0.48 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N3—H3⋯O5 0.88 2.60 3.296 (4) 136
N3—H3⋯O6 0.88 1.82 2.684 (4) 166
N11—H11A⋯O3i 0.88 2.18 3.042 (4) 166
N11—H11B⋯O1Wii 0.88 2.13 2.989 (4) 164
N12—H12A⋯N21 0.88 2.04 2.915 (4) 174
N12—H12B⋯O2iii 0.88 2.25 2.904 (4) 131
N12—H12B⋯O6 0.88 2.58 3.260 (4) 135
N13—H13A⋯N22iv 0.88 2.13 3.012 (4) 176
N13—H13B⋯O5 0.88 2.03 2.870 (4) 159
N23—H23⋯O2Wv 0.88 1.94 2.793 (4) 164
N31—H31A⋯O3Wvi 0.88 2.06 2.870 (4) 153
N31—H31B⋯O2iii 0.88 2.22 3.048 (4) 157
N32—H32A⋯N1vii 0.88 2.06 2.933 (4) 173
N32—H32B⋯O3viii 0.88 2.11 2.817 (4) 137
N33—H33A⋯N2 0.88 2.09 2.973 (4) 177
N33—H33B⋯O1Wii 0.88 2.19 2.850 (4) 132
N50—H50⋯O1iii 0.93 2.28 2.969 (4) 130
C55—H55A⋯O4ix 0.99 2.55 3.470 (5) 154
O1W—H1AW⋯O1x 0.84 (2) 2.02 (2) 2.856 (4) 172 (4)
O1W—H1BW⋯O2 0.84 (2) 1.98 (3) 2.775 (3) 157 (4)
O2W—H2AW⋯O3xi 0.83 (2) 2.57 (3) 3.265 (4) 143 (4)
O2W—H2AW⋯O4xi 0.83 (2) 2.38 (3) 3.168 (4) 159 (4)
O2W—H2BW⋯O4 0.81 (2) 2.08 (2) 2.812 (4) 150 (4)
O3W—H3AW⋯O4 0.84 (2) 1.95 (3) 2.768 (4) 163 (5)
O3W—H3BW⋯O5xi 0.83 (2) 1.96 (3) 2.773 (4) 165 (5)
Symmetry codes: (i) x, y, z-1; (ii) x+1, y, z-1; (iii) -x+1, -y+1, -z+1; (iv) x, y-1, z; (v) -x+2, -y+1, -z; (vi) -x+2, -y+1, -z+1; (vii) x, y+1, z; (viii) x, y+1, z-1; (ix) x-1, y, z; (x) -x, -y+1, -z+1; (xi) -x+2, -y, -z+1.

Data collection: X-AREA (Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA, X-RED and X-SHAPE. Stoe & Cie, Darmstadt, Germany.]); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA, X-RED and X-SHAPE. Stoe & Cie, Darmstadt, Germany.]); program(s) used to solve structure: SHELXS86 (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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.

Supporting information

CCDC reference: 966425

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536813028250/zl2565sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813028250/zl2565Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813028250/zl2565Isup3.cdx

Supporting information file. DOI: 10.1107/S1600536813028250/zl2565Isup4.cml

checkCIF report


Comment top

Melamine is an organic base with a pronounced tendency to form hydrogen-bonded architectures in combination with carboxylic acids. Many of these compounds display common structural features and normally these are best classed as salts with full proton transfer to form melaminium cations. These melaminium cations then form hydrogen-bonded tapes composed of N–H···N hydrogen bonds. The tapes have a propensity to assemble into π-stacks and between these stacks are located the carboxylates. Several examples with simple alkyl carboxylic acids (see for example Perpétuo & Janczak, 2002) and dicarboxylic acids are known (such as Froschauer and Weil, 2012 & Eppel and Bernstein, 2009). Those with three carboxylic acid groups are less common (Huczynski et al., 2009; Eshtiagh-Hosseini et al., 2010; Perpetuo and Janczak, 2003). We set out to explore the effect of introducing multiple carboxylic acid groups with a flexible geometry through the use of nitrilotriacetic acid, N(CH2COOH)3.

The title compound, 1, crystallizes in the triclinic space group P1. The asymmetric unit (illustrated in Figure 1) contains two crystallographically independent melaminium cations, the nitrilotriacetate anion and three water molecules. The crystal examined was found to be twinned by a 2-fold rotation about [100] corresponding to the twin law (1 0 0 0.422 -1 0 0.051 0 -1). It was possible to index the diffraction images using two twin domains. The integration procedure employed both twin domains. The structure was refined using all observed data using the HKLF5 formalism within SHELXL97. The relative amount of the two components was refined to be 0.5918: 0.4082 (14).

The assignment of hydrogen bonding between different components was greatly facilitated by the identification of hydrogen atoms with final difference Fourier maps. Examination of hydrogen locations reveals that crystallization of this compound is associated with proton migration from acid to the base. All three of the carboxylic acid groups are deprotonated. Two carboxylic protons migrate to one of the endocyclic N atoms in each melamine moiety giving rise to two melaminium cations. The third carboxylic acid proton migrates to the central nitrogen in the nitrilotriacetic acid moiety to generate an anion correctly called 2,2',2''-ammoniotriacetate. As in similar cases full proton transfer means these compounds are best described as salts rather than co-crystals. The assignment of the carboxylates is in line with work of Childs et al. (2007) who noted that a similarity in C—O bond lengths (ΔDC—O < 0.03 Å) is indicative of carboxylate rather than carboxylic acid. For the three COO groups in the anion, the mean C—O bond length is 1.253 (3) Å, but the deviation from equal values for the three pairs of C–O distances are 0.02, 0.008, and 0.003 Å. Similarly, examination of the bond angles in the endocyclic protonated nitrogen in both melamine moieties reveals that there is a marked bond angle increase in the aromatic ring at the protonated nitrogen compared to the unprotonated endocyclic nitrogen atoms. This agrees with the work of Hingerty et al. (1981) who reported an increase in bond angle at the endocyclic nitrogen atoms upon protonation. At the protonated N atoms the bond angles are 119.1 (2) and 119.3 (2) ° compared with the other C—N—C bond angles which have a mean of 115.8 (2) °.

The two melaminium cations form hydrogen bonded tapes sustained by N—H···N interactions, common to many other similar compounds. Pairs of N—H···N interactions between adjacent melaminium cations form embraces with graph set notation R22(8) (Etter et al., 1990). There are two symmetry independent embraces of this type which assemble the melaminium cations into tapes that extend parallel to the crystallographic [010] direction. These tapes are stacked parallel to the a axis at a mean separation of a/2 (3.3559 (11) Å) suggestive of π-stacking. A single tape is illustrated in Figure 2. Between the tapes lie the [HN(CH2COO)3]2- anions and water molecules. Each carboxylate acts as a hydrogen bond acceptor to amino groups of the melaminium cations. In this way the anions are involved in N—H···O hydrogen bonds between different tapes within the same stack and between different stacks. Additional N—H···O and O—H···O hydrogen bonds formed by the water molecules present further help to knit together the cations and anions. Full details of the hydrogen bonds present are contained within Table 1. The crystal packing within 1 is represented in Figure 3.

The crystal structures of melamine with monocarboxylic acids form a well established family of compounds. Similarly linear dicarboxylic acid salts of melamine are well illustrated. These have similar structural features (the π-stacking of tapes of melaminium held together by R22(8) embraces). The structure of 1 shows analogous features to those of simpler carboxylates.

Related literature top

For compounds of melamine with simple carboxylic acid, see, for example: Froschauer & Weil (2012); Eppel & Bernstein (2009); Perpétuo & Janczak (2002). For those with tricarboxylic acids, see: Eshtiagh-Hosseini et al. (2010); Huczynski et al. (2009); Perpetuo & Janczak (2003). For assignment of protonation on the grounds of bond angle and bond length, see: Childs et al. (2007) and Hingerty et al. (1981), respectively. An introduction to graph-set theory may be found in Etter et al. (1990).

Experimental top

Melamine (0.334 g, 2 mmol) and nitrilotriacetic acid (0.249 g,1 mmol) were dissolved in 50:50 ethanol:water (20 ml) and stirred for 15 min. The solution was left unperturbed for slow solvent evaporation in suitably sized vials. After approximately 3 days, colourless needle-shaped crystals were obtained.

Refinement top

The crystal examined was found to be twinned by a 2-fold rotation about [100]. The twinning was apparent in the diffraction images. The twin law was identified by inspection of reciprocal space within X-AREA (Stoe & Cie, 2002). It was possible to index the diffraction images using two twin domains. The integration procedure employed both twin domains. The structure was refined using all observed data using the HKLF5 formalism within SHELXL97. The relative amount of the two components was refined to be 0.5918: 0.4082 (14). Refinement using a single twin domain was not satisfactory as approximately 40% of the spots from the first domain were overlapped by those from the second domain.

Hydrogen atoms were located in difference Fourier maps. Those on the organic components were placed with a riding model with Uiso set to 1.2 times the Ueq of the atom on which they ride. Hydrogen atoms attached to water were refined subject to sensible bond length and bond angle restraints with Uiso values set at 1.5 times the Ueq of the central oxygen atom.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS86 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. ORTEP representation of the assymetric unit of 1 with atoms drawn as 50% thermal ellipsoids. Dashed lines indicate hydrogen bonds.
[Figure 2] Fig. 2. Single hydrogen-bonded tape formed from melaminium cations. Hydrogen bonds are represented as dashed lines. Symmetry equivalent atoms are generated by i = x, 1+y, z..
[Figure 3] Fig. 3. Crystal packing within 1 viewed down [010]. Stacks of hydrogen-bonded tapes are linked by hydrogen bonds to the anion and water. Dashed lines indicate hydrogen bonds.
Bis(2,4,6-triamino-1,3,5-triazin-1-ium) 2-[bis(carboxylatomethyl)azaniumyl]acetate trihydrate top
Crystal data top
2C3H7N6+·C6H7NO62−·3H2OZ = 2
Mr = 497.43F(000) = 524
Triclinic, P1Dx = 1.570 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.7117 (11) ÅCell parameters from 4000 reflections
b = 12.1495 (19) Åθ = 1.7–29.5°
c = 13.102 (3) ŵ = 0.13 mm−1
α = 82.714 (15)°T = 150 K
β = 89.252 (16)°Needle, colourless
γ = 83.238 (13)°0.36 × 0.16 × 0.04 mm
V = 1052.4 (3) Å3
Data collection top
Stoe IPDS2
diffractometer		10946 independent reflections
Radiation source: fine-focus sealed tube5515 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.000
Detector resolution: 6.67 pixels mm-1θmax = 25.3°, θmin = 1.7°
ω scansh = −8→7
Absorption correction: analytical
(X-RED and X-SHAPE; Stoe & Cie, 2002)		k = −14→14
Tmin = 0.957, Tmax = 0.994l = −15→15
10946 measured reflections
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)] = 0.084Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.244H atoms treated by a mixture of independent and constrained refinement
S = 0.95 w = 1/[σ2(Fo2) + (0.1396P)2]
where P = (Fo2 + 2Fc2)/3
10946 reflections(Δ/σ)max < 0.001
327 parametersΔρmax = 0.40 e Å−3
10 restraintsΔρmin = −0.48 e Å−3
Crystal data top
2C3H7N6+·C6H7NO62−·3H2Oγ = 83.238 (13)°
Mr = 497.43V = 1052.4 (3) Å3
Triclinic, P1Z = 2
a = 6.7117 (11) ÅMo Kα radiation
b = 12.1495 (19) ŵ = 0.13 mm−1
c = 13.102 (3) ÅT = 150 K
α = 82.714 (15)°0.36 × 0.16 × 0.04 mm
β = 89.252 (16)°
Data collection top
Stoe IPDS2
diffractometer		10946 independent reflections
Absorption correction: analytical
(X-RED and X-SHAPE; Stoe & Cie, 2002)		5515 reflections with I > 2σ(I)
Tmin = 0.957, Tmax = 0.994Rint = 0.000
10946 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.08410 restraints
wR(F2) = 0.244H atoms treated by a mixture of independent and constrained refinement
S = 0.95Δρmax = 0.40 e Å−3
10946 reflectionsΔρmin = −0.48 e Å−3
327 parameters
Special details top

Experimental. a face indexed abosorption correction was applied. this utilised the Tompa method implmented within Stoe X-Area.

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
C10.7947 (5)0.3396 (3)−0.0788 (3)0.0284 (8)
C20.7256 (5)0.4231 (3)0.0654 (3)0.0282 (8)
C30.7125 (5)0.2304 (3)0.0665 (3)0.0269 (8)
N10.7670 (4)0.2371 (2)−0.0319 (2)0.0288 (7)
N20.7753 (4)0.4355 (2)−0.0339 (2)0.0283 (7)
N30.6891 (4)0.3237 (2)0.1167 (2)0.0308 (7)
H30.65080.31890.18150.037*
N110.8471 (4)0.3485 (2)−0.1770 (2)0.0312 (7)
H11A0.86260.2887−0.20930.037*
H11B0.86650.4140−0.21010.037*
N120.7108 (4)0.5111 (2)0.1170 (2)0.0330 (7)
H12A0.73370.57680.08560.040*
H12B0.67810.50370.18260.040*
N130.6798 (4)0.1346 (2)0.1184 (3)0.0329 (7)
H13A0.69390.07350.08820.039*
H13B0.64380.13140.18340.039*
C210.7361 (5)0.8238 (3)0.0554 (3)0.0282 (8)
C220.7847 (5)0.9412 (3)−0.0907 (3)0.0284 (8)
C230.7972 (5)0.7470 (3)−0.0937 (3)0.0295 (8)
N210.7571 (4)0.7302 (2)0.0062 (2)0.0283 (7)
N220.7439 (4)0.9294 (2)0.0094 (2)0.0298 (7)
N230.8157 (4)0.8499 (2)−0.1437 (2)0.0293 (7)
H230.84720.8584−0.20940.035*
N310.7031 (4)0.8087 (2)0.1552 (2)0.0337 (7)
H31A0.68690.86640.19010.040*
H31B0.69740.74090.18700.040*
N320.7965 (5)1.0404 (2)−0.1423 (2)0.0348 (7)
H32A0.77731.1004−0.11060.042*
H32B0.82371.0467−0.20850.042*
N330.8209 (4)0.6595 (2)−0.1465 (2)0.0309 (7)
H33A0.81000.5920−0.11500.037*
H33B0.84750.6691−0.21270.037*
N500.6450 (4)0.3141 (2)0.5208 (2)0.0274 (6)
H500.60990.37990.47710.033*
C510.5536 (5)0.3342 (3)0.6213 (3)0.0312 (8)
H51A0.64030.37720.65770.037*
H51B0.54470.26180.66410.037*
C520.3453 (5)0.3985 (3)0.6077 (3)0.0310 (8)
C530.8705 (5)0.2958 (3)0.5187 (3)0.0293 (8)
H53A0.92350.36120.54180.035*
H53B0.91490.29110.44690.035*
C540.9599 (5)0.1904 (3)0.5862 (3)0.0306 (8)
C550.5523 (5)0.2261 (3)0.4741 (3)0.0289 (8)
H55A0.41210.22480.49830.035*
H55B0.62710.15210.49700.035*
C560.5540 (5)0.2475 (3)0.3566 (3)0.0321 (8)
O10.2949 (4)0.4461 (2)0.5204 (2)0.0343 (6)
O20.2429 (4)0.4017 (2)0.6894 (2)0.0354 (6)
O30.8994 (4)0.1721 (2)0.6763 (2)0.0393 (7)
O41.0971 (4)0.1308 (2)0.5460 (2)0.0509 (8)
O50.4934 (4)0.1730 (2)0.3111 (2)0.0375 (6)
O60.6089 (4)0.3375 (2)0.3162 (2)0.0366 (6)
O1W−0.1047 (4)0.5512 (2)0.6739 (2)0.0350 (6)
H1AW−0.152 (6)0.546 (4)0.616 (2)0.053*
H1BW0.012 (4)0.520 (3)0.667 (3)0.053*
O2W1.0355 (5)0.0954 (2)0.3413 (2)0.0458 (7)
H2AW1.002 (8)0.032 (2)0.355 (4)0.069*
H2BW1.087 (7)0.117 (4)0.3894 (16)0.069*
O3W1.4067 (5)0.0556 (2)0.6843 (2)0.0460 (7)
H3AW1.302 (5)0.067 (4)0.648 (4)0.069*
H3BW1.455 (7)−0.010 (2)0.679 (4)0.069*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0177 (17)0.0277 (19)0.039 (2)−0.0022 (13)−0.0022 (15)−0.0002 (16)
C20.0198 (17)0.0231 (18)0.041 (2)−0.0033 (13)−0.0019 (15)−0.0003 (15)
C30.0167 (16)0.0252 (18)0.038 (2)−0.0027 (13)−0.0014 (15)−0.0003 (16)
N10.0241 (15)0.0238 (15)0.0374 (18)−0.0041 (12)−0.0017 (13)0.0018 (13)
N20.0287 (15)0.0220 (15)0.0340 (17)−0.0041 (12)−0.0011 (13)−0.0011 (13)
N30.0306 (16)0.0251 (15)0.0363 (18)−0.0063 (12)0.0025 (13)0.0000 (13)
N110.0342 (16)0.0253 (15)0.0340 (18)−0.0061 (12)0.0023 (13)−0.0009 (13)
N120.0413 (18)0.0236 (15)0.0348 (18)−0.0078 (12)0.0050 (14)−0.0033 (13)
N130.0350 (17)0.0230 (15)0.0407 (19)−0.0083 (12)0.0041 (14)0.0005 (14)
C210.0200 (17)0.0247 (18)0.038 (2)−0.0021 (13)−0.0007 (15)0.0027 (16)
C220.0236 (18)0.0228 (18)0.039 (2)−0.0023 (13)−0.0027 (15)−0.0047 (16)
C230.0191 (17)0.0218 (18)0.047 (2)−0.0013 (13)−0.0018 (15)−0.0051 (16)
N210.0263 (15)0.0221 (15)0.0360 (18)−0.0036 (11)0.0008 (13)−0.0011 (13)
N220.0281 (15)0.0254 (16)0.0353 (18)−0.0023 (12)0.0002 (13)−0.0027 (13)
N230.0297 (16)0.0222 (15)0.0354 (17)−0.0043 (12)−0.0018 (13)0.0009 (13)
N310.0356 (17)0.0254 (16)0.0396 (19)−0.0038 (13)0.0031 (14)−0.0029 (14)
N320.0462 (18)0.0241 (16)0.0337 (18)−0.0043 (13)0.0028 (15)−0.0021 (14)
N330.0326 (16)0.0215 (15)0.0373 (18)−0.0020 (12)0.0022 (13)0.0000 (13)
N500.0253 (15)0.0250 (15)0.0314 (16)−0.0067 (11)0.0026 (12)0.0019 (12)
C510.0286 (19)0.0328 (19)0.032 (2)−0.0057 (14)0.0007 (15)−0.0028 (16)
C520.0275 (18)0.0283 (19)0.038 (2)−0.0097 (14)0.0008 (16)−0.0031 (17)
C530.0252 (18)0.0302 (19)0.032 (2)−0.0037 (14)0.0039 (15)−0.0006 (16)
C540.0225 (18)0.0301 (19)0.040 (2)−0.0041 (14)−0.0017 (16)−0.0066 (17)
C550.0293 (18)0.0261 (18)0.031 (2)−0.0056 (14)0.0010 (15)−0.0025 (16)
C560.0263 (19)0.029 (2)0.040 (2)−0.0057 (15)−0.0002 (16)0.0005 (17)
O10.0307 (13)0.0319 (14)0.0381 (16)−0.0018 (10)−0.0008 (11)0.0028 (12)
O20.0302 (14)0.0356 (14)0.0395 (15)−0.0013 (10)0.0061 (12)−0.0041 (12)
O30.0345 (15)0.0348 (15)0.0441 (17)0.0033 (11)0.0022 (13)0.0049 (13)
O40.0479 (17)0.0594 (19)0.0383 (16)0.0229 (14)0.0003 (14)−0.0058 (14)
O50.0387 (15)0.0350 (14)0.0406 (15)−0.0095 (11)0.0011 (12)−0.0068 (12)
O60.0425 (15)0.0343 (14)0.0331 (15)−0.0087 (12)−0.0005 (12)−0.0001 (12)
O1W0.0300 (14)0.0362 (15)0.0379 (15)−0.0015 (11)0.0013 (12)−0.0033 (12)
O2W0.0554 (18)0.0409 (17)0.0435 (17)−0.0172 (14)0.0046 (14)−0.0040 (14)
O3W0.0483 (18)0.0360 (15)0.0522 (19)0.0020 (13)−0.0064 (14)−0.0056 (14)
Geometric parameters (Å, º) top
C1—N111.324 (5)N32—H32B0.8800
C1—N11.350 (4)N33—H33A0.8800
C1—N21.362 (4)N33—H33B0.8800
C2—N121.329 (4)N50—C511.482 (4)
C2—N21.334 (5)N50—C551.496 (4)
C2—N31.353 (4)N50—C531.504 (5)
C3—N131.312 (4)N50—H500.9300
C3—N11.330 (5)C51—C521.520 (5)
C3—N31.373 (4)C51—H51A0.9900
N3—H30.8800C51—H51B0.9900
N11—H11A0.8800C52—O11.247 (5)
N11—H11B0.8800C52—O21.267 (4)
N12—H12A0.8800C53—C541.525 (5)
N12—H12B0.8800C53—H53A0.9900
N13—H13A0.8800C53—H53B0.9900
N13—H13B0.8800C54—O31.246 (5)
C21—N311.317 (5)C54—O41.256 (4)
C21—N221.353 (4)C55—C561.528 (5)
C21—N211.368 (4)C55—H55A0.9900
C22—N321.315 (4)C55—H55B0.9900
C22—N221.329 (5)C56—O61.247 (4)
C22—N231.375 (4)C56—O51.253 (4)
C23—N211.328 (5)O1W—H1AW0.84 (2)
C23—N331.333 (4)O1W—H1BW0.84 (2)
C23—N231.355 (4)O2W—H2AW0.83 (2)
N23—H230.8800O2W—H2BW0.81 (2)
N31—H31A0.8800O3W—H3AW0.84 (2)
N31—H31B0.8800O3W—H3BW0.83 (2)
N32—H32A0.8800
N11—C1—N1117.6 (3)C22—N32—H32B120.0
N11—C1—N2116.6 (3)H32A—N32—H32B120.0
N1—C1—N2125.8 (3)C23—N33—H33A120.0
N12—C2—N2119.4 (3)C23—N33—H33B120.0
N12—C2—N3118.1 (3)H33A—N33—H33B120.0
N2—C2—N3122.5 (3)C51—N50—C55112.0 (3)
N13—C3—N1121.0 (3)C51—N50—C53115.8 (3)
N13—C3—N3118.1 (3)C55—N50—C53112.2 (3)
N1—C3—N3120.9 (3)C51—N50—H50105.2
C3—N1—C1116.5 (3)C55—N50—H50105.2
C2—N2—C1115.0 (3)C53—N50—H50105.2
C2—N3—C3119.2 (3)N50—C51—C52111.3 (3)
C2—N3—H3120.4N50—C51—H51A109.4
C3—N3—H3120.4C52—C51—H51A109.4
C1—N11—H11A120.0N50—C51—H51B109.4
C1—N11—H11B120.0C52—C51—H51B109.4
H11A—N11—H11B120.0H51A—C51—H51B108.0
C2—N12—H12A120.0O1—C52—O2126.5 (3)
C2—N12—H12B120.0O1—C52—C51118.3 (3)
H12A—N12—H12B120.0O2—C52—C51115.1 (3)
C3—N13—H13A120.0N50—C53—C54113.7 (3)
C3—N13—H13B120.0N50—C53—H53A108.8
H13A—N13—H13B120.0C54—C53—H53A108.8
N31—C21—N22118.1 (3)N50—C53—H53B108.8
N31—C21—N21116.6 (3)C54—C53—H53B108.8
N22—C21—N21125.2 (3)H53A—C53—H53B107.7
N32—C22—N22121.2 (3)O3—C54—O4125.1 (3)
N32—C22—N23117.8 (3)O3—C54—C53118.9 (3)
N22—C22—N23121.0 (3)O4—C54—C53115.9 (3)
N21—C23—N33118.9 (3)N50—C55—C56111.5 (3)
N21—C23—N23122.2 (3)N50—C55—H55A109.3
N33—C23—N23119.0 (3)C56—C55—H55A109.3
C23—N21—C21115.6 (3)N50—C55—H55B109.3
C22—N22—C21116.5 (3)C56—C55—H55B109.3
C23—N23—C22119.4 (3)H55A—C55—H55B108.0
C23—N23—H23120.3O6—C56—O5126.9 (4)
C22—N23—H23120.3O6—C56—C55117.4 (3)
C21—N31—H31A120.0O5—C56—C55115.6 (3)
C21—N31—H31B120.0H1AW—O1W—H1BW100 (4)
H31A—N31—H31B120.0H2AW—O2W—H2BW113 (4)
C22—N32—H32A120.0H3AW—O3W—H3BW105 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3···O50.882.603.296 (4)136
N3—H3···O60.881.822.684 (4)166
N11—H11A···O3i0.882.183.042 (4)166
N11—H11B···O1Wii0.882.132.989 (4)164
N12—H12A···N210.882.042.915 (4)174
N12—H12B···O2iii0.882.252.904 (4)131
N12—H12B···O60.882.583.260 (4)135
N13—H13A···N22iv0.882.133.012 (4)176
N13—H13B···O50.882.032.870 (4)159
N23—H23···O2Wv0.881.942.793 (4)164
N31—H31A···O3Wvi0.882.062.870 (4)153
N31—H31B···O2iii0.882.223.048 (4)157
N32—H32A···N1vii0.882.062.933 (4)173
N32—H32B···O3viii0.882.112.817 (4)137
N33—H33A···N20.882.092.973 (4)177
N33—H33B···O1Wii0.882.192.850 (4)132
N50—H50···O1iii0.932.282.969 (4)130
C55—H55A···O4ix0.992.553.470 (5)154
O1W—H1AW···O1x0.84 (2)2.02 (2)2.856 (4)172 (4)
O1W—H1BW···O20.84 (2)1.98 (3)2.775 (3)157 (4)
O2W—H2AW···O3xi0.83 (2)2.57 (3)3.265 (4)143 (4)
O2W—H2AW···O4xi0.83 (2)2.38 (3)3.168 (4)159 (4)
O2W—H2BW···O40.81 (2)2.08 (2)2.812 (4)150 (4)
O3W—H3AW···O40.84 (2)1.95 (3)2.768 (4)163 (5)
O3W—H3BW···O5xi0.83 (2)1.96 (3)2.773 (4)165 (5)
Symmetry codes: (i) x, y, z−1; (ii) x+1, y, z−1; (iii) −x+1, −y+1, −z+1; (iv) x, y−1, z; (v) −x+2, −y+1, −z; (vi) −x+2, −y+1, −z+1; (vii) x, y+1, z; (viii) x, y+1, z−1; (ix) x−1, y, z; (x) −x, −y+1, −z+1; (xi) −x+2, −y, −z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3···O50.882.603.296 (4)136.3
N3—H3···O60.881.822.684 (4)165.7
N11—H11A···O3i0.882.183.042 (4)165.5
N11—H11B···O1Wii0.882.132.989 (4)164.1
N12—H12A···N210.882.042.915 (4)173.9
N12—H12B···O2iii0.882.252.904 (4)130.7
N12—H12B···O60.882.583.260 (4)134.6
N13—H13A···N22iv0.882.133.012 (4)176.3
N13—H13B···O50.882.032.870 (4)159.2
N23—H23···O2Wv0.881.942.793 (4)164.2
N31—H31A···O3Wvi0.882.062.870 (4)153.2
N31—H31B···O2iii0.882.223.048 (4)156.9
N32—H32A···N1vii0.882.062.933 (4)173.3
N32—H32B···O3viii0.882.112.817 (4)137.4
N33—H33A···N20.882.092.973 (4)176.9
N33—H33B···O1Wii0.882.192.850 (4)131.7
N50—H50···O1iii0.932.282.969 (4)130.1
C55—H55A···O4ix0.992.553.470 (5)154.0
O1W—H1AW···O1x0.84 (2)2.02 (2)2.856 (4)172 (4)
O1W—H1BW···O20.84 (2)1.98 (3)2.775 (3)157 (4)
O2W—H2AW···O3xi0.83 (2)2.57 (3)3.265 (4)143 (4)
O2W—H2AW···O4xi0.83 (2)2.38 (3)3.168 (4)159 (4)
O2W—H2BW···O40.81 (2)2.082 (17)2.812 (4)150 (4)
O3W—H3AW···O40.84 (2)1.95 (3)2.768 (4)163 (5)
O3W—H3BW···O5xi0.83 (2)1.96 (3)2.773 (4)165 (5)
Symmetry codes: (i) x, y, z−1; (ii) x+1, y, z−1; (iii) −x+1, −y+1, −z+1; (iv) x, y−1, z; (v) −x+2, −y+1, −z; (vi) −x+2, −y+1, −z+1; (vii) x, y+1, z; (viii) x, y+1, z−1; (ix) x−1, y, z; (x) −x, −y+1, −z+1; (xi) −x+2, −y, −z+1.
 

Acknowledgements

KH thanks the University of Hull for the award of a PhD studentship.

References

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Journal logoCRYSTALLOGRAPHIC
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ISSN: 2056-9890
Volume 69| Part 11| November 2013| Pages o1674-o1675
doi:10.1107/S1600536813028250
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