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Volume 69 
Part 1 
Page o57  
January 2013  

Received 6 November 2012
Accepted 4 December 2012
Online 8 December 2012

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.002 Å
R = 0.034
wR = 0.090
Data-to-parameter ratio = 11.9
Details
Open access

Glycine-phthalic acid (1/1)

aSchool of Physics, Bharathidasan University, Tiruchirappalli 620 024, India,bDepartment of Physics and Nanotechnology, SRM University, Kattankulathur 603 203, India, and cDepartment of Bioinformatics, School of Chemical and Biotechnology, SASTRA University, Thanjavur 613 401, India
Correspondence e-mail: thamu@scbt.sastra.edu

In the title compound, C2H5NO2·C8H6O4, the glycine molecule exists as a zwitterion (2-azaniumylethanoate) with a positively charged amino group and a negatively charged carboxylate group. In the crystal, N-H...O and O-H...O hydrogen bonds link the components into layers parallel to the ab plane. The central part of each layer is composed of hydrogen-bonded glycine zwitterions, while phthalic acid molecules interact with the zwitterions in such a way that benzene rings protrude up and down from the layer.

Related literature

For related structures, see: Losev et al. (2011[Losev, E. A., Zakharov, B. A., Drebushchak, T. N. & Boldyreva, E. V. (2011). Acta Cryst. C67, o297-o300.]); Herbstein et al. (1981[Herbstein, F. H., Kapon, M., Maor, I. & Reisner, G. M. (1981). Acta Cryst. B37, 136-140.]). For graph-set 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.]). For head-to-tail hydrogen bonds, see: Sharma et al. (2006[Sharma, A., Thamotharan, S., Roy, S. & Vijayan, M. (2006). Acta Cryst. C62, o148-o152.]); Selvaraj et al. (2007[Selvaraj, M., Thamotharan, S., Roy, S. & Vijayan, M. (2007). Acta Cryst. B63, 459-468.]).

[Scheme 1]

Experimental

Crystal data
  • C2H5NO2·C8H6O4

  • Mr = 241.20

  • Orthorhombic, P b c a

  • a = 7.9657 (5) Å

  • b = 11.3470 (7) Å

  • c = 23.513 (2) Å

  • V = 2125.3 (3) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.13 mm-1

  • T = 173 K

  • 0.53 × 0.46 × 0.30 mm

Data collection
  • Stoe IPDS diffractometer

  • 15716 measured reflections

  • 2077 independent reflections

  • 1597 reflections with I > 2[sigma](I)

  • Rint = 0.041

Refinement
  • R[F2 > 2[sigma](F2)] = 0.034

  • wR(F2) = 0.090

  • S = 1.01

  • 2077 reflections

  • 175 parameters

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

  • [Delta][rho]max = 0.22 e Å-3

  • [Delta][rho]min = -0.19 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1A...O5i 0.917 (19) 1.992 (19) 2.8398 (16) 153.0 (16)
N1-H1B...O3ii 0.91 (2) 2.13 (2) 3.0219 (16) 164.6 (17)
N1-H1C...O2iii 0.88 (2) 2.181 (19) 2.8934 (16) 137.4 (15)
N1-H1C...O3iv 0.88 (2) 2.416 (19) 3.0681 (16) 130.9 (15)
O4-H4O...O2i 0.96 (3) 1.58 (3) 2.5383 (14) 175 (2)
O6-H6O...O1v 0.98 (2) 1.56 (2) 2.5337 (13) 171 (2)
Symmetry codes: (i) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]; (ii) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]; (iii) [-x+{\script{3\over 2}}, y+{\script{1\over 2}}, z]; (iv) x+1, y, z; (v) -x+1, -y, -z.

Data collection: EXPOSE in IPDS-I Software (Stoe & Cie, 2000[Stoe & Cie (2000). IPDS-I Software. Stoe & Cie GmbH, Darmstadt, Germany.]); cell refinement: CELL in IPDS-I Software; data reduction: INTEGRATE in IPDS-I Software; 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV5360 ).


Acknowledgements

TB thanks the University Grants Commission (UGC) for the award of a Research Fellowship under the Faculty Improvement Programme (FIP). We are grateful to Professor Helen Stoeckli-Evans, University of Neuchâtel, Switzerland, for measuring the X-ray diffraction data. ST thanks the management of SASTRA University for their encouragement.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Herbstein, F. H., Kapon, M., Maor, I. & Reisner, G. M. (1981). Acta Cryst. B37, 136-140.  [CrossRef] [ISI] [details]
Losev, E. A., Zakharov, B. A., Drebushchak, T. N. & Boldyreva, E. V. (2011). Acta Cryst. C67, o297-o300.  [CSD] [CrossRef] [details]
Selvaraj, M., Thamotharan, S., Roy, S. & Vijayan, M. (2007). Acta Cryst. B63, 459-468.  [ISI] [CSD] [CrossRef] [ChemPort] [details]
Sharma, A., Thamotharan, S., Roy, S. & Vijayan, M. (2006). Acta Cryst. C62, o148-o152.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Stoe & Cie (2000). IPDS-I Software. Stoe & Cie GmbH, Darmstadt, Germany.


Acta Cryst (2013). E69, o57  [ doi:10.1107/S160053681204977X ]

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