1,3-Bis[(6-methyl-2-pyrid­yl)meth­yl]imidazolium bromide

Kim, G.Y.; Park, S.-K.; Lee, D.-H.; Park, G.

doi:10.1107/S1600536809006710

Volume 65
Part 3
Page o637
March 2009

Received 20 January 2009
Accepted 24 February 2009
Online 28 February 2009

Key indicators
Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.004 Å
R = 0.037
wR = 0.094
Data-to-parameter ratio = 19.5
Details

1,3-Bis[(6-methyl-2-pyridyl)methyl]imidazolium bromide

Ga Young Kim,^a Sang-Kyu Park,^a Dong-Heon Lee ^a ^* and Gyungse Park ^b ^*

^aDepartment of Chemistry, Chonbuk National University, Jeonju, Chonbuk 561-756, Republic of Korea, and ^bDepartment of Chemistry, Kunsan National University, Kusan, Chonbuk 573-701, Republic of Korea
Correspondence e-mail: dhl@chonbuk.ac.kr, parkg@kunsan.ac.kr

The title compound, C₁₇H₁₉N₄⁺·Br^-, is built up from 1,3-bis[(6-methyl-2-pyridinyl)methyl]imidazolium cations and bromide anions. Each of two 6-methyl-2-pyridyl rings is rotated out of the imidazole plane, making dihedral angles of 79.90 (9) and 86.40 (9)°. The packing is consolidated by aromatic [pi] - [pi] interactions between the pyridine rings of neighbouring molecules [centroid-centroid distance = 3.554 (2) Å] and by weak C-HN and C-HBr hydrogen bonds.

Related literature

For the synthesis of N-heterocyclic carbenes, see: Arduengo et al. (1991); Enders et al. (1996); Frenzel et al. (1999); Gardiner et al. (1999); Herrmann et al. (1998); McGuinness et al. (1998); Öfele (1968); Wanzlick & Schonherr (1968); Wanzlick & Schönherr (1968); Zhang & Trudell (2000). For related structures, see: Weskamp et al. (1999ab).

Experimental

Crystal data

C₁₇H₁₉N₄⁺·Br^-
M_r = 359.27
Monoclinic, P 2₁ /c
a = 8.2951 (4) Å
b = 12.4992 (5) Å
c = 16.1786 (7) Å
= 95.709 (1)°
V = 1669.11 (13) Å³
Z = 4
Mo K radiation
= 2.47 mm^-1
T = 173 K
0.40 × 0.25 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.439, T_max = 0.709
10482 measured reflections
3923 independent reflections
2861 reflections with I > 2(I)
R_int = 0.070

Refinement

R[F² > 2(F²)] = 0.037
wR(F²) = 0.094
S = 1.00
3923 reflections
201 parameters
H-atom parameters constrained
_max = 0.92 e Å^-3
_min = -0.50 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C7-H7AN4ⁱ	0.99	2.34	3.308 (4)	165
C7-H7BBrⁱⁱ	0.99	2.79	3.660 (3)	147
C9-H9ABr	0.95	2.91	3.695 (3)	141
C10-H10ABrⁱ	0.95	2.68	3.521 (3)	148
C11-H11ABr	0.99	2.93	3.801 (3)	147
C11-H11BBrⁱ	0.99	2.89	3.690 (3)	138
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[-x, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

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: 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: LX2088 ).

References

Arduengo, A. J. III, Harlow, R. L. & Kline, M. (1991). J. Am. Chem. Soc. 113, 361-363.
Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison,Wisconsin, USA.
Enders, D., Gielen, H., Raabe, G., Runsink, J. & Teles, J. H. (1996). Chem. Ber. 129, 1483-1488.
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Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Wanzlick, H.-W. & Schönherr, H.-J. (1968). Angew. Chem. Int. Ed. Engl. 7, 141-142.
Weskamp, T., Böhm, V. P. W. & Herrmann, W. A. (1999a). J. Organomet. Chem. 585, 348-352.
Weskamp, T., Kohl, F. J., Hieringer, W., Gleich, D. W. & Herrmann, W. A. (1999b). Angew. Chem. Int. Ed. 38, 2416-2419.
Zhang, C. & Trudell, M. L. (2000). Tetrahedron Lett. 41, 595-598.

organic compounds