1-[6-(Hydroxy­meth­yl)-2-pyrid­yl]-3-(2,4,6-trimethyl­benz­yl)-1H-imidazol-3-ium bromide

Zhou, C.; Zhou, X.-G.; Qiu, Y.-P.; Luo, M.-M.

doi:10.1107/S1600536808034764

Volume 64
Part 11
Page o2225
November 2008

Received 18 October 2008
Accepted 24 October 2008
Online 31 October 2008

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.003 Å
R = 0.044
wR = 0.116
Data-to-parameter ratio = 19.0
Details

1-[6-(Hydroxymethyl)-2-pyridyl]-3-(2,4,6-trimethylbenzyl)-1H-imidazol-3-ium bromide

Chuang Zhou,^a Xiang-Ge Zhou,^a Yu-Ping Qiu ^a and Mei-Ming Luo ^a ^*

^aKey Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, People's Republic of China
Correspondence e-mail: luomm@scu.edu.cn

In the title compound, C₁₉H₂₂N₃O⁺·Br^-, the imidazole ring is approximately coplanar with the pyridine ring [dihedral angle = 0.88 (13)°] and nearly perpendicular to the benzene ring [dihedral angle = 81.70 (13)°]. O-HBr and C-HBr hydrogen bonding helps to stabilize the crystal structure.

Related literature

For general background, see: Liddle et al. (2007); Ren et al. (2007); Arnold & Wilson (2007); Chianese & Crabtree (2005); Dyson et al. (2008); Patel et al. (2006). For synthesis, see: Hosseinzadeh et al. (2006).

Experimental

Crystal data

C₁₉H₂₂N₃O⁺·Br^-
M_r = 388.31
Monoclinic, P 2₁ /c
a = 11.2315 (3) Å
b = 11.5390 (3) Å
c = 14.3673 (4) Å
= 100.833 (2)°
V = 1828.82 (9) Å³
Z = 4
Mo K radiation
= 2.26 mm^-1
T = 296 (2) K
0.50 × 0.48 × 0.40 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.320, T_max = 0.405
13818 measured reflections
4184 independent reflections
2287 reflections with I > 2(I)
R_int = 0.048

Refinement

R[F² > 2(F²)] = 0.044
wR(F²) = 0.116
S = 1.01
4184 reflections
220 parameters
H-atom parameters constrained
_max = 0.41 e Å^-3
_min = -0.60 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1ABr1	0.82	2.49	3.227 (2)	151
C7-H7ABr1ⁱ	0.93	2.75	3.598 (2)	152
C8-H8ABr1ⁱⁱ	0.93	2.89	3.745 (2)	154
C10-H10BBr1ⁱ	0.97	2.91	3.813 (2)	155
Symmetry codes: (i) -x, -y, -z; (ii) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2459 ).

Acknowledgements

Financial support of this work by the Natural Science Foundation of Sichuan Province of China is gratefully acknowledged.

References

Arnold, P. L. & Wilson, C. (2007). Inorg. Chim. Acta, 360, 190-196.
Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Chianese, A. R. & Crabtree, R. H. (2005). Organometallics, 24, 4432-4436.
Dyson, G., Frison, J., Simonovic, S., Whitwood, A. C. & Douthwaite, R. E. (2008). Organometallics, 27, 281-288.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Hosseinzadeh, R., Tajbakhsh, M. & Alikarami, M. (2006). Tetrahedron Lett. 47, 5203-5205.
Liddle, S. T., Edworthy, I. S. & Arnold, P. L. (2007). Chem. Soc. Rev. 36, 1732-1744.
Patel, D., Liddle, S. T., Mungur, S. A., Rodden, M., Blake, A. J. & Arnold, P. L. (2006). Chem. Commun. 6, 1124-1126.
Ren, H. P., Yao, P. Y., Xu, S. S., Song, H. B. & Wang, B. Q. (2007). J. Organomet. Chem. 692, 2092-2098.
Sheldrick, G. M. (1996). SADABS. University of Göttinger, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds