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Volume 66 
Part 5 
Pages o1125-o1126  
May 2010  

Received 18 March 2010
Accepted 15 April 2010
Online 21 April 2010

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Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.005 Å
R = 0.045
wR = 0.109
Data-to-parameter ratio = 7.3
Details
Open access

(2S*)-2-Ammonio-3-(1H-indol-3-yl)propionate pyridine-2,4-dicarboxylic acid ethanol solvate

Kai Dia*

aCollege of Chemistry and Chemical Engineering, Qiqihar University, Qiqihar 161006, People's Republic of China
Correspondence e-mail: dikai09@sohu.com

In the title compound, C11H12N2O2·C7H5NO4·C2H6O, the (2S*)-2-amino-3-(1H-indol-3-yl)propionic acid is present in the zwitterionic form. In the crystal structure, 2-amino-3-(1H-indol-3-yl)propionic acid molecules and pyridine-2,4-dicarboxylic acid molecules are linked through strong intermolecular O-H...O and N-H...O hydrogen bonds, forming layers parallel to (100). The layers are linked through the ethanol molecules via somewhat weaker intermolecular O-H...O and N-H...O hydrogen bonds, forming thus a three-dimensional network. Weak C-H...O and N-H...N hydrogen bonding and [pi]-[pi] interactions between the aromatic rings are also present.

Related literature

For supramolecular structures with imino, carboxylate and pyridine groups interconnected via intermolecular hydrogen bonds, see: Broker & Tiekink (2010[Broker, G. A. & Tiekink, E. R. T. (2010). Acta Cryst. E66, o705.]); Hemamalini & Fun (2010[Hemamalini, M. & Fun, H.-K. (2010). Acta Cryst. E66, o689-o690.]); Narimani & Yamin (2010[Narimani, L. & Yamin, B. M. (2010). Acta Cryst. E66, o669.]); Pourayoubi et al. (2010[Pourayoubi, M., Toghraee, M., Rheingold, A. L. & Golen, J. A. (2010). Acta Cryst. E66, o844.]). For a description of the Cambridge Structural Database, see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]). For hydrogen bonding, see: Desiraju & Steiner (1999[Desiraju, G. R. & Steiner, T. (1999). The Weak Hydrogen Bond in Structural Chemistry and Biology, IUCr Monographs on Crystallography, Vol. 9, p. 13. Oxford University Press.]).

[Scheme 1]

Experimental

Crystal data

  • C11H12N2O2·C7H5NO4·C2H6O

  • Mr = 417.41

  • Triclinic, P 1

  • a = 7.0320 (14) Å

  • b = 7.7590 (16) Å

  • c = 9.5800 (19) Å

  • [alpha] = 85.44 (3)°

  • [beta] = 81.89 (3)°

  • [gamma] = 71.84 (3)°

  • V = 491.34 (19) Å3

  • Z = 1

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 298 K

  • 0.27 × 0.23 × 0.22 mm
Data collection

  • Bruker SMART 1000 CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.971, Tmax = 0.977

  • 4115 measured reflections

  • 2092 independent reflections

  • 1815 reflections with I > 2[sigma](I)

  • Rint = 0.024
Refinement

  • R[F2 > 2[sigma](F2)] = 0.045

  • wR(F2) = 0.109

  • S = 1.02

  • 2092 reflections

  • 285 parameters

  • 6 restraints

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

  • [Delta][rho]max = 0.18 e Å-3

  • [Delta][rho]min = -0.22 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N3-H3C...N1i 0.89 2.15 3.032 (4) 170
N3-H3B...O7ii 0.89 1.90 2.787 (4) 171
N3-H3A...O3 0.89 2.01 2.894 (4) 170
N2-H2A...O5iii 0.90 (1) 2.06 (2) 2.922 (4) 161 (4)
O7-H7...O5iii 0.86 (1) 1.96 (3) 2.762 (4) 155 (5)
O1-H1...O6iii 0.90 (5) 1.58 (6) 2.479 (3) 177 (5)
O4-H4...O2iv 0.88 (1) 1.79 (2) 2.611 (3) 155 (5)
C20-H20A...O6v 0.97 2.59 3.200 (6) 122
Symmetry codes: (i) x, y-1, z; (ii) x-1, y, z+1; (iii) x, y, z-1; (iv) x, y, z+1; (v) x+1, y, z-1.

Table 2
[pi]-[pi] interactions (Å)

Cg1, Cg2 and Cg3 are the centroids of the N2,C9,C8,C14,C15 (pyrrole), C8-C13 (benzene) and N1,C1-C5 (pyridine) rings, respectively.
Cg1...Cg3i 3.665 (2) Cg2...Cg3i 3.722 (2)
Cg1...Cg3ii 3.683 (2) Cg2...Cg3ii 3.701 (2)
Symmetry codes: (i) 1 + x, -1 + y, z; (ii) x, -1 + y, z.

Data collection: SMART (Bruker, 1998[Bruker (1998). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1998[Bruker (1998). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FB2190 ).

References

Allen, F. H. (2002). Acta Cryst. B58, 380-388.  [ISI] [CrossRef] [details]
Broker, G. A. & Tiekink, E. R. T. (2010). Acta Cryst. E66, o705.  [CrossRef] [details]
Bruker (1998). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.
Desiraju, G. R. & Steiner, T. (1999). The Weak Hydrogen Bond in Structural Chemistry and Biology, IUCr Monographs on Crystallography, Vol. 9, p. 13. Oxford University Press.
Hemamalini, M. & Fun, H.-K. (2010). Acta Cryst. E66, o689-o690.  [CrossRef] [details]
Narimani, L. & Yamin, B. M. (2010). Acta Cryst. E66, o669.  [CrossRef] [details]
Pourayoubi, M., Toghraee, M., Rheingold, A. L. & Golen, J. A. (2010). Acta Cryst. E66, o844.  [CrossRef] [details]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]

Acta Cryst (2010). E66, o1125-o1126   [ doi:10.1107/S1600536810014017 ]

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