1-Carboxy­methyl-2-ethyl-4-methyl-1H-imidazol-3-ium chloride monohydrate

Chen, C.-Q.; Luo, S.-N.; Lin, J.-G.; Qiu, L.; Xia, Y.-M.

doi:10.1107/S1600536809013403

Volume 65
Part 5
Page o1081
May 2009

Received 27 March 2009
Accepted 9 April 2009
Online 22 April 2009

Key indicators
Single-crystal X-ray study
T = 93 K
Mean (C-C) = 0.002 Å
R = 0.036
wR = 0.099
Data-to-parameter ratio = 17.5
Details

1-Carboxymethyl-2-ethyl-4-methyl-1H-imidazol-3-ium chloride monohydrate

Chuan-Qing Chen,^a Shi-Neng Luo,^b ^* Jian-Guo Lin,^b Ling Qiu ^b and Yong-Mei Xia ^a

^aSchool of Chemical and Materials Engineering, Jiangnan University, Wuxi 214122, People's Republic of China, and ^bThe Key Laboratory of Nuclear Medicine, Ministry of Health, Jiangsu Institute of Nuclear Medicine, Wuxi, 214063, People's Republic of China
Correspondence e-mail: shineng914@yahoo.com.cn

In the title compound, C₈H₁₃N₂O₂⁺·Cl^-·H₂O, the methyl C atom of the ethyl group is slightly out of the imidazole plane, with an N-C(ring)-C-C torsion angle of -15.1 (2)°. In the crystal structure, there are strong intermolecular hydrogen-bonding interactions between the solvent water molecule, the free chloride anion and the organic cation, resulting in a two-dimensional supramolecular network in the ab plane.

Related literature

The title compound is a vital intermediate in the synthesis of bisphosphonic acid, i.e. 2-(2-ethyl-4-methyl-1H-imidazol-1-yl)-1-hydroxyethane-1,1-diyldiphosphonic acid; for a general background on bisphosphonates, see: Dawson (2003); Vasireddy et al. (2003). For related structures, see: Gao et al. (2004); Barczynski et al. (2008). For the synthesis, see: Zederenko et al. (1994).

Experimental

Crystal data

C₈H₁₃N₂O₂⁺·Cl^-·H₂O
M_r = 222.67
Monoclinic, P 2₁ /n
a = 11.077 (2) Å
b = 8.4542 (18) Å
c = 11.938 (3) Å
= 90.265 (3)°
V = 1117.9 (4) Å³
Z = 4
Mo K radiation
= 0.33 mm^-1
T = 93 K
0.40 × 0.40 × 0.35 mm

Data collection

Rigaku SPIDER diffractometer
Absorption correction: multi-scan (RAPID-AUTO; Rigaku, 2004) T_min = 0.880, T_max = 0.894
8869 measured reflections
2532 independent reflections
2203 reflections with I > 2(I)
R_int = 0.031

Refinement

R[F² > 2(F²)] = 0.036
wR(F²) = 0.099
S = 1.00
2532 reflections
145 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
_max = 0.29 e Å^-3
_min = -0.20 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1NCl1	0.881 (17)	2.300 (18)	3.1635 (14)	166.6 (15)
O3-H3ACl1	0.91 (2)	2.20 (2)	3.1062 (14)	177 (2)
O1-H1OO3ⁱ	0.96 (2)	1.60 (2)	2.5557 (16)	170 (2)
O3-H3BCl1ⁱⁱ	0.96 (2)	2.14 (2)	3.0860 (14)	168.2 (19)
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: RAPID-AUTO (Rigaku, 2004); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FJ2205 ).

Acknowledgements

This work was supported by the Wu Jieping Medical Fund (32067500615) and the National Natural Science Foundation of China (No. 20801024).

References

Barczynski, P., Komasa, A., Ratajczak-Sitarz, M., Katrusiak, A., Huczynki, A. & Brzezinski, B. (2008). J. Mol. Struct. 876, 170-176.
Dawson, N. A. (2003). Exp. Opin. Pharmacother. 4, 705-716.
Gao, S., Zhao, H., Huo, L.-H., Gao, J.-S., Zain, S. M. & Ng, S. W. (2004). Acta Cryst. E60, o1391-o1393.
Rigaku (2004). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Vasireddy, S., Talwakar, A., Miller, H., Mehan, H. & David, R. S. (2003). Clin. Rheumatol. 22, 376-380.
Zederenko, P., Gil, M. S. & Ballesteros, P. (1994). J. Org. Chem. 59, 6268-6273.

organic compounds