Glycine–phthalic acid (1/1)

Balakrishnan, T.; Ramamurthi, K.; Thamotharan, S.

doi:10.1107/S160053681204977X

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 (C-C) = 0.002 Å
R = 0.034
wR = 0.090
Data-to-parameter ratio = 11.9
Details

Glycine-phthalic acid (1/1)

T. Balakrishnan,^a K. Ramamurthi ^b and S. Thamotharan ^c ^*

^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-HO and O-HO 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); Herbstein et al. (1981). For graph-set motifs, see: Bernstein et al. (1995). For head-to-tail hydrogen bonds, see: Sharma et al. (2006); Selvaraj et al. (2007).

Experimental

Crystal data

C₂H₅NO₂·C₈H₆O₄
M_r = 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 radiation
= 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(I)
R_int = 0.041

Refinement

R[F² > 2(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
_max = 0.22 e Å^-3
_min = -0.19 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1AO5ⁱ	0.917 (19)	1.992 (19)	2.8398 (16)	153.0 (16)
N1-H1BO3ⁱⁱ	0.91 (2)	2.13 (2)	3.0219 (16)	164.6 (17)
N1-H1CO2ⁱⁱⁱ	0.88 (2)	2.181 (19)	2.8934 (16)	137.4 (15)
N1-H1CO3^iv	0.88 (2)	2.416 (19)	3.0681 (16)	130.9 (15)
O4-H4OO2ⁱ	0.96 (3)	1.58 (3)	2.5383 (14)	175 (2)
O6-H6OO1^v	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); cell refinement: CELL in IPDS-I Software; data reduction: INTEGRATE in IPDS-I Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009) and ORTEP-3 for Windows (Farrugia, 2012); 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.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Herbstein, F. H., Kapon, M., Maor, I. & Reisner, G. M. (1981). Acta Cryst. B37, 136-140.
Losev, E. A., Zakharov, B. A., Drebushchak, T. N. & Boldyreva, E. V. (2011). Acta Cryst. C67, o297-o300.
Selvaraj, M., Thamotharan, S., Roy, S. & Vijayan, M. (2007). Acta Cryst. B63, 459-468.
Sharma, A., Thamotharan, S., Roy, S. & Vijayan, M. (2006). Acta Cryst. C62, o148-o152.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Stoe & Cie (2000). IPDS-I Software. Stoe & Cie GmbH, Darmstadt, Germany.

organic compounds