l-Asparagine–l-tartaric acid (1/1)

Natarajan, S.; Hema, V.; Sundar, J.K.; Suresh, J.; Lakshman, P.L.N.

doi:10.1107/S1600536810030771

Volume 66
Part 9
Page o2239
September 2010

Received 18 July 2010
Accepted 2 August 2010
Online 11 August 2010

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.009 Å
R = 0.053
wR = 0.226
Data-to-parameter ratio = 6.2
Details

L-Asparagine-L-tartaric acid (1/1)

S. Natarajan,^a V. Hema,^a J. Kalyana Sundar,^a J. Suresh ^b and P. L. Nilantha Lakshman ^c ^*

^aDepartment of Physics, Madurai Kamaraj University, Madurai 625 021, India,^bDepartment of Physics, The Madura College, Madurai 625 011, India, and ^cDepartment of Food Science and Technology, University of Ruhuna, Mapalana, Kamburupitiya (81100), Sri Lanka
Correspondence e-mail: plakshmannilantha@ymail.com

In the title compound, C₄H₈N₂O₃·C₄H₆O₆, the amino acid molecule exists as a zwitterion and the carboxylic acid in an un-ionized state. The tartaric acid molecules are linked into layers parallel to the ab plane by O-HO hydrogen bonds. The amino acid molecules are also linked into layers parallel to the ab plane by N-HO and C-HO hydrogen bonds. The alternating tartaric acid and amino acid layers are linked into a three-dimensional framework by N-HO and O-HO hydrogen bonds.

Related literature

Our interest in the determination of the structure of the title compound is due to recent advances in organic non-linear optical (NLO) materials on account of their widespread potential industrial applications. For studies on organic non-linear optical materials, see: Cole et al. (2000); Ravi et al. (1998); Sarma et al. (1997).

Experimental

Crystal data

C₄H₈N₂O₃·C₄H₆O₆
M_r = 282.21
Monoclinic, P 2₁
a = 5.0860 (4) Å
b = 9.6720 (6) Å
c = 11.8340 (8) Å
= 95.311 (8)°
V = 579.64 (7) Å³
Z = 2
Mo K radiation
= 0.15 mm^-1
T = 293 K
0.28 × 0.23 × 0.21 mm

Data collection

Nonius MACH-3 diffractometer
Absorption correction: scan (North et al., 1968) T_min = 0.959, T_max = 0.969
1339 measured reflections
1073 independent reflections
1015 reflections with I > 2(I)
R_int = 0.095
2 standard reflections every 60 min intensity decay: none

Refinement

R[F² > 2(F²)] = 0.053
wR(F²) = 0.226
S = 1.38
1073 reflections
172 parameters
1 restraint
H-atom parameters constrained
_max = 0.34 e Å^-3
_min = -0.40 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1AO5ⁱ	0.86	2.23	3.053 (8)	160
N1-H1BO3ⁱⁱ	0.86	2.04	2.856 (9)	159
N2-H2AO8ⁱⁱⁱ	0.89	2.19	2.895 (8)	136
N2-H2BO2^iv	0.89	2.28	2.921 (9)	129
N2-H2CO7	0.89	2.06	2.912 (8)	160
N2-H2CO8	0.89	2.30	2.916 (8)	126
O4-H4O1^v	0.82	1.69	2.500 (6)	168
O6-H6O4^vi	0.82	2.19	2.959 (8)	156
O7-H7O6ⁱⁱⁱ	0.82	2.05	2.850 (7)	166
O9-H9O2^vii	0.82	1.75	2.570 (7)	180
C2-H2O2ⁱⁱⁱ	0.98	2.56	3.426 (9)	147
C3-H3AO3ⁱⁱ	0.97	2.40	3.158 (10)	134
Symmetry codes: (i) $[-x, y+{\script{1\over 2}}, -z]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z+1]$ ; (iii) x-1, y, z; (iv) $[-x+1, y-{\script{1\over 2}}, -z+1]$ ; (v) $[-x, y-{\script{1\over 2}}, -z]$ ; (vi) $[-x+1, y+{\script{1\over 2}}, -z]$ ; (vii) $[-x+2, y-{\script{1\over 2}}, -z+1]$ .

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI5134 ).

Acknowledgements

SN thanks the CSIR for the funding provided under the Emeritus Scientist Scheme. JS thanks the management of The Madura College, Madurai, and DST-FIST for funding.

References

Cole, J. M., Wilson, C. C., Howard, J. A. K. & Cruickshank, F. R. (2000). Acta Cryst. B56, 1085-1093.
Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.
Harms, K. & Wocadlo, S. (1996). XCAD4. University of Marburg, Germany.
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.
Ravi, M., Gangopadhyay, P., Rao, D. N., Cohen, S., Agranat, I. & Radhakrishnan, T. P. (1998). Chem. Mater. 10, 2371-2377.
Sarma, J. A. R. P., Allen, F. H., Hoy, V. J., Howard, J. A. K., Thaimattam, R., Biradha, K. & Desiraju, G. R. (1997). J. Chem. Soc. Chem. Commun. pp. 101-102.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds