dl-Asparaginium nitrate

Moussa Slimane, N.; Cherouana, A.; Bendjeddou, L.; Dahaoui, S.; Lecomte, C.

doi:10.1107/S1600536809031730

Volume 65
Part 9
Pages o2180-o2181
September 2009

Received 5 June 2009
Accepted 11 August 2009
Online 19 August 2009

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R = 0.035
wR = 0.087
Data-to-parameter ratio = 16.4
Details

DL-Asparaginium nitrate

Nabila Moussa Slimane,^a Aouatef Cherouana,^a ^* Lamia Bendjeddou,^a Slimane Dahaoui ^b and Claude Lecomte ^b

^aLaboratoire de Chimie Moléculaire, du Contrôle, de l'Environnement et des Mesures Physico-Chimiques, Faculté des Sciences, Département de Chimie, Université Mentouri de Constantine, 25000 Constantine, Algeria, and ^bCristallographie, Résonance Magnétique et Modélisation (CRM2), Université Henri Poincaré, Nancy 1, Faculté des Sciences, BP 70239, 54506 Vandoeuvre lès Nancy CEDEX, France
Correspondence e-mail: c_aouatef@yahoo.fr

In the title compound, C₄H₉N₂O₃⁺·NO₃^-, alternatively called (1RS)-2-carbamoyl-1-carboxyethanaminium nitrate, the asymmetric unit comprises one asparaginium cation and one nitrate anion. The strongest cation-cation O-HO hydrogen bond in the structure, together with other strong cation-cation N-HO hydrogen bonds, generates a succession of infinite chains of R₂²(8) rings along the b axis. Additional cation-cation C-HO hydrogen bonds link these chains into two-dimensional layers formed by alternating R₄⁴(24) and R₄²(12) rings. Connections between these layers are provided by the strong cation-anion N-HO hydrogen bonds, as well as by one weak C-HO interaction, thus forming a three-dimensional network. Some of the cation-anion N-HO hydrogen bonds are bifurcated of the type D-H(A₁,A₂).

Related literature

DL-Asparagine has been used in growth media for bacteria, see: Gerhardt & Wilson (1948); Palleroni et al. (1973); Wagtendonk et al. (1963). For related structures, see Aarthy et al. (2005); Anitha et al. (2005); Arnold et al. (2000); Flaig et al. (2002); Kartha & de Vries (1961); Ramanadham et al. (1972); Smirnova et al. (1990); Verbist et al. (1972); Wang et al. (1985); Weisinger-Lewin et al. (1989); Yamada et al. (2007). For hydrogen bonding, see: Desiraju & Steiner (1999). For hydrogen-bond morifs, see: Bernstein et al. (1995); Etter et al. (1990).

Experimental

Crystal data

C₄H₉N₂O₃⁺·NO₃^-
M_r = 195.14
Monoclinic, P 2₁ /c
a = 7.923 (2) Å
b = 9.608 (2) Å
c = 10.613 (3) Å
= 107.105 (2)°
V = 772.2 (3) Å³
Z = 4
Mo K radiation
= 0.16 mm^-1
T = 100 K
0.30 × 0.20 × 0.09 mm

Data collection

Oxford Diffraction Xcalibur-Sapphire2 CCD diffractometer
Absorption correction: gaussian (CrysAlis RED; Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction, Wroclaw, Poland.]$ ) T_min = 0.966, T_max = 0.991
19446 measured reflections
2236 independent reflections
1804 reflections with I > 2(I)
R_int = 0.036

Refinement

R[F² > 2(F²)] = 0.035
wR(F²) = 0.087
S = 1.07
2236 reflections
136 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.45 e Å^-3
_min = -0.19 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1O3ⁱ	0.845 (16)	1.736 (16)	2.571 (2)	169.0 (17)
N2-H1NO4ⁱⁱ	0.899 (15)	1.962 (15)	2.822 (2)	159.6 (13)
N2-H2NO3	0.907 (15)	2.406 (16)	2.965 (2)	119.9 (12)
N2-H2NO5	0.907 (15)	2.233 (14)	3.024 (2)	145.4 (13)
N2-H2NO6	0.907 (15)	2.474 (15)	3.039 (2)	120.7 (11)
N2-H3NO4ⁱⁱⁱ	0.903 (14)	2.454 (14)	3.157 (2)	135.0 (12)
N2-H3NO6ⁱⁱⁱ	0.903 (14)	2.068 (15)	2.957 (2)	168.3 (14)
N3-H5NO2^iv	0.893 (16)	2.064 (15)	2.924 (2)	161.4 (15)
C3-H3O5^v	0.99	2.36	3.086 (2)	130
C3-H4O2^v	0.99	2.39	3.313 (2)	156
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[-x, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) -x, -y+1, -z+1; (iv) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (v) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction, Wroclaw, Poland.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction, Wroclaw, Poland.]$ ); data reduction: CrysAlis RED; program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Farrugia, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FB2157 ).

Acknowledgements

Technical support (X-ray measurements at SCDRX) from Université Henry Poincaré, Nancy 1, is gratefully acknowledged.

References

Aarthy, A., Anitha, K., Athimoolam, S., Bahadur, S. A. & Rajaram, R. K. (2005). Acta Cryst. E61, o2042-o2044.
Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.
Anitha, K., Athimoolam, S. & Rajaram, R. K. (2005). Acta Cryst. E61, o1463-o1465.
Arnold, W. D., Sanders, L. K., McMahon, M. T., Volkov, A. V., Wu, G., Coppens, P., Wilson, S. R., Godbout, N. & Oldfield, E. (2000). J. Am. Chem. Soc. 122, 4708-4717.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Desiraju, G. R. & Steiner, T. (1999). The Weak Hydrogen Bond in Structural Chemistry and Biology, p. 66. International Union of Crystallography Monographs on Crystallography. New York: Oxford University Press Inc.
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Flaig, R., Koritsanszky, T., Dittrich, B., Wagner, A. & Luger, P. (2002). J. Am. Chem. Soc. 124, 3407-3417.
Gerhardt, P. & Wilson, J. B. (1948). J. Bacteriol. 56, 17-24.
Kartha, G. & de Vries, A. (1961). Nature (London), 192, 862-863.
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.
Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction, Wroclaw, Poland.
Palleroni, N. J., Kunisawa, R., Contopoulou, R. & Doudoroff, M. (1973). Int. J. Syst. Bacteriol. 23, 333-339.
Ramanadham, M., Sikka, S. K. & Chidambaram, R. (1972). Acta Cryst. B28, 3000-3005.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Smirnova, V. I., Sorokina, N. I., Safonov, A. A., Verin, I. A. & Tischenko, G. N. (1990). Kristallografiya, 35, 50-53.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Verbist, J. J., Lehmann, M. S., Koetzle, T. F. & Hamilton, W. C. (1972). Acta Cryst. B28, 3006-3013.
Wagtendonk, W. J. van, Clark, J. A. D. & Godoy, G. A. (1963). Proc. Natl Acad. Sci. USA, 50, 835-838.
Wang, J. L., Berkovitch-Yellin, Z. & Leiserowitz, L. (1985). Acta Cryst. B41, 341-348.
Weisinger-Lewin, Y., Frolow, F., McMullan, R. K., Koetzle, T. F., Lahav, M. & Leiserowitz, L. (1989). J. Am. Chem. Soc. 111, 1035-1040.
Yamada, K., Hashizume, D., Shimizu, T. & Yokoyama, S. (2007). Acta Cryst. E63, o3802-o3803.

organic compounds