dl-Tyrosinium chloride dihydrate

Guenifa, F.; Bendjeddou, L.; Cherouana, A.; Dahaoui, S.; Lecomte, C.

doi:10.1107/S1600536812043899

Volume 68
Part 11
Pages o3227-o3228
November 2012

Received 24 September 2012
Accepted 23 October 2012
Online 27 October 2012

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R = 0.032
wR = 0.084
Data-to-parameter ratio = 20.0
Details

DL-Tyrosinium chloride dihydrate

Fatiha Guenifa,^a Lamia Bendjeddou,^a ^* Aouatef Cherouana,^a Slimane Dahaoui ^b and Claude Lecomte ^b

^aUnité de Recherche Chimie de l'Environnement et Moleculaire Structurale, (CHEMS), Faculté des Sciences Exactes, Campus Chaabet Ersas, 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: Lamiabendjeddou@yahoo.fr

In the title compound, C₉H₁₂NO₃⁺·Cl^-·2H₂O, the cation has a protonated amino group resulting from proton transfer from chloridric acid. The structure displays double layers parallel to the [010] direction held together by N-HO, N-HCl, O-HO and O-HCl hydrogen bonds. These layers are stacked along the c axis at b = 1/2; within each layer, the tyrosinium cations are arranged in an alternating head-to-tail sequence, forming inversion dimers [R₂²(10) motif]. The water molecules allow for the construction of a three-dimensional hydrogen-bonded network formed by centrosymmetric R₆⁶(28) and R₈⁸(34) motifs.

Related literature

For other examples of organic salts of amino acids, see: Zeghouan et al. (2012); Guenifa et al. (2009). For the structure of bis(L-tyrosinium) sulfate monohydrate, see: Sridhar et al. (2002). For other examples of amino acids with non-polar side chains, see: Torii & Iitaka (1973); Harding & Long (1968). For graph-set notation, see: Bernstein et al. (1995).

Experimental

Crystal data

C₉H₁₂NO₃⁺·Cl^-·2H₂O
M_r = 253.68
Triclinic, $[P \overline 1]$
a = 5.3330 (2) Å
b = 10.9634 (5) Å
c = 11.2500 (4) Å
= 113.642 (4)°
= 94.359 (3)°
= 98.465 (3)°
V = 589.34 (5) Å³
Z = 2
Mo K radiation
= 0.33 mm^-1
T = 100 K
0.3 × 0.03 × 0.02 mm

Data collection

Oxford Diffraction Xcalibur Sapphire CCD diffractometer
12044 measured reflections
3445 independent reflections
2780 reflections with I > 2(I)
R_int = 0.034

Refinement

R[F² > 2(F²)] = 0.032
wR(F²) = 0.084
S = 1.02
3445 reflections
172 parameters
11 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.43 e Å^-3
_min = -0.30 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1NCl1	0.90 (1)	2.36 (1)	3.2326 (12)	162 (1)
N1-H2NCl1ⁱ	0.92 (1)	2.44 (1)	3.2872 (12)	154 (1)
N1-H2NO3ⁱ	0.92 (1)	2.40 (2)	2.9574 (15)	119 (1)
N1-H3NCl1ⁱⁱ	0.90 (1)	2.32 (1)	3.2151 (12)	176 (1)
O1-H1Cl1ⁱⁱⁱ	0.84 (2)	2.36 (2)	3.1858 (11)	169 (1)
O2-H2O2Wⁱ	0.89 (1)	1.64 (1)	2.5319 (15)	174 (2)
O1W-H11WO1^iv	0.84 (1)	2.10 (1)	2.9044 (13)	162 (2)
O1W-H12WCl1^v	0.85 (1)	2.33 (1)	3.1784 (11)	172 (2)
O2W-H21WO1Wⁱ	0.83 (1)	1.91 (1)	2.7429 (14)	173 (2)
O2W-H22WO1W^vi	0.85 (2)	2.02 (2)	2.8318 (15)	161 (2)
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) x+1, y, z; (iii) -x+1, -y+1, -z+2; (iv) x, y, z-1; (v) -x, -y+1, -z+1; (vi) x+1, y-1, z.

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 $[Oxford Diffraction. (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction, Wroclaw, Poland.]$ ); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2008 $[Oxford Diffraction. (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction, Wroclaw, Poland.]$ ); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999), PARST97 (Nardelli, 1995), Mercury (Macrae et al., 2006) and POVRay (Persistence of Vision Team, 2004)'.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NK2187 ).

Acknowledgements

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

References

Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Guenifa, F., Bendjeddou, L., Cherouana, A., Dahaoui, S. & Lecomte, C. (2009). Acta Cryst. E65, o2264-o2265.
Harding, M. M. & Long, H. A. (1968). Acta Cryst. B24, 1096-1102.
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.
Nardelli, M. (1995). J. Appl. Cryst. 28, 659.
Oxford Diffraction. (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction, Wroclaw, Poland.
Persistence of Vision Team (2004). POV-RAY. Persistence of Vision Raytracer Pty Ltd, Victoria, Australia. URL: http://www.povray.org/ .
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Sridhar, B., Srinivasan, N. & Rajaram, R. K. (2002). Acta Cryst. E58, o211-o214.
Torii, K. & Iitaka, Y. (1973). Acta Cryst. B29, 2799-2807.
Zeghouan, O., Bendjeddou, L., Cherouana, A., Dahaoui, S. & Lecomte, C. (2012). Acta Cryst. E68, o2959-o2960.

organic compounds