1-[(1-Methyl-1H-imidazol-5-yl)meth­yl]-1H-indole-5-carbonitrile

de Jager, J.J.; Smith, V.J.

doi:10.1107/S1600536812048404

Volume 68
Part 12
Page o3486
December 2012

Received 22 November 2012
Accepted 26 November 2012
Online 30 November 2012

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R = 0.042
wR = 0.113
Data-to-parameter ratio = 20.0
Details

1-[(1-Methyl-1H-imidazol-5-yl)methyl]-1H-indole-5-carbonitrile

Josephus Jacobus de Jager ^a ^* and Vincent J. Smith ^a

^aDepartment of Chemistry and Polymer Science, Stellenbosch University, Private Bag X1, Matieland 7602, South Africa
Correspondence e-mail: jjdj@sun.ac.za

In the title compound, C₁₄H₁₂N₄, the dihedral angle between the indole ring system (r.m.s. deviation = 0.010 Å) and the imidazole ring is 77.70 (6)°. In the crystal, molecules are linked by C-HN hydrogen bonds. One set of hydrogen bonds forms an undulating chain running parallel to the b-axis direction, while the other undulating chain is parallel to the c-axis direction. In combination, (100) sheets result.

Related literature

For background to farnesyl transferase, see: Chakrabarti et al. (2002). For the properties of related compounds, see: Bulbule et al. (2008), van Voorhis et al. (2007); de Ruyck & Wouters (2008).

Experimental

Crystal data

C₁₄H₁₂N₄
M_r = 236.28
Monoclinic, P 2₁ /n
a = 10.9624 (16) Å
b = 7.8687 (12) Å
c = 14.292 (2) Å
= 106.727 (2)°
V = 1180.6 (3) Å³
Z = 4
Mo K radiation
= 0.08 mm^-1
T = 100 K
0.10 × 0.10 × 0.02 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009) T_min = 0.992, T_max = 0.998
36857 measured reflections
3286 independent reflections
2643 reflections with I > 2(I)
R_int = 0.042

Refinement

R[F² > 2(F²)] = 0.042
wR(F²) = 0.113
S = 1.06
3286 reflections
164 parameters
H-atom parameters constrained
_max = 0.32 e Å^-3
_min = -0.21 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C4-H4N4ⁱ	0.95	2.53	3.4588 (18)	167
C13-H13N4ⁱⁱ	0.95	2.57	3.4010 (18)	147
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{5\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001; Atwood et al., 2003); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB7000 ).

Acknowledgements

The authors wish to thank W. A. L. van Otterlo, S. C. Pelly and the National Research Foundation for financial assistance and academic guidance.

References

Atwood, J. L. & Barbour, L. J. (2003). Cryst. Growth Des. 3, 3-8.
Barbour, L. J. (2001). Supramol. Chem. 1, 189-191.
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bulbule, V. J., Rivas, K., Verlinde, C. L. M. J., Van Voorhis, W. C. & Gelb, M. H. (2008). J. Med. Chem. 51, 384-387.
Chakrabarti, D., Da Silva, T., Barger, J., Paquette, S., Patel, H., Patterson, S. & Allen, C. M. (2002). J. Biol. Chem. 277, 42066-42073.
Ruyck, J. de & Wouters, J. (2008). Curr. Protein Pept. Sci. 9, 117-137.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Voorhis, W. C. van, Rivas, K. L., Bendale, P., Nallan, L., Horney, C., Barrett, L. K., Bauer, K. D., Smart, B. P., Ankala, S., Hucke, O., Verlinde, C. L. M. J., Chakrabart, D., Strickland, C., Yokoyama, K., Buckner, F. S., Hamilton, A. D., Williams, D. K., Lombardo, L. J., Floyd, D. & Gelb, H. (2007). Antimicrob. Agents Chemother. 51, 3659-3671.

organic compounds