tert-Butyl 4-formyl-1H-imidazole-1-carboxyl­ate

Kang, J.-T.; Li, Z.-G.; Xu, J.-W.; Wei, Y.

doi:10.1107/S1600536810029247

Volume 66
Part 8
Page o2185
August 2010

Received 20 February 2010
Accepted 22 July 2010
Online 31 July 2010

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.005 Å
R = 0.062
wR = 0.149
Data-to-parameter ratio = 13.6
Details

tert-Butyl 4-formyl-1H-imidazole-1-carboxylate

Jun-Tao Kang,^a Zhi-Gang Li,^a Jing-Wei Xu ^a ^* and Yang Wei ^a ^*

^aThe State Key Laboratory of Electroanalytical Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, People's Republic of China
Correspondence e-mail: jwxu@ciac.jl.cn, yangwei1988@ciac.jl.cn

In the crystal structure of the title compound, C₉H₁₂N₂O₃, weak intermolecular C-HO hydrogen bonds link the molecules into chains. Further weak C-HO hydrogen bonds together with [pi] - [pi] interactions [centroid-centroid distance = 3.672 (4) Å] between neighbouring chains lead to a double-chain structure propagating in [100].

Related literature

For uses of imidazole direvatives, see: Matuszak et al. (1976), Verras et al. (2004). For the synthesis of the title compound, see: Metobo et al. (2006).

Experimental

Crystal data

C₉H₁₂N₂O₃
M_r = 196.21
Triclinic, $[P \overline 1]$
a = 5.972 (3) Å
b = 7.173 (7) Å
c = 12.164 (11) Å
= 79.630 (16)°
= 86.620 (15)°
= 89.326 (15)°
V = 511.7 (8) Å³
Z = 2
Mo K radiation
= 0.10 mm^-1
T = 293 K
0.14 × 0.11 × 0.03 mm

Data collection

Bruker APEX CCD area detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001) T_min = 0.987, T_max = 0.997
2633 measured reflections
1769 independent reflections
915 reflections with I > 2(I)
R_int = 0.022

Refinement

R[F² > 2(F²)] = 0.062
wR(F²) = 0.149
S = 0.99
1769 reflections
130 parameters
H-atom parameters constrained
_max = 0.17 e Å^-3
_min = -0.17 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C2-H2O3ⁱ	0.93	2.36	3.251 (5)	160
C9-H9CO1ⁱⁱ	0.96	2.65	3.531 (5)	153
Symmetry codes: (i) x+1, y, z; (ii) -x+1, -y+1, -z+1.

Data collection: SMART (Bruker, 2007); cell refinement: SAINT-Plus (Bruker, 2007); data reduction: SAINT-Plus; 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: SU2164 ).

Acknowledgements

This work was supported by the State Key Laboratory of Electroanalytical Chemistry, Changchun Institute of Applied Chemistry.

References

Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2007). SMART and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.
Matuszak, C. A. & Matuszak, A. J. (1976). J. Chem. Educ. 53, 280-284.
Metobo, S. E., Jin, H. L., Tsiang, M. & Kim, C. U. (2006). Bioorg. Med. Chem. Lett. 16, 3985-3988.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Verras, A., Kuntz, I. D. & Ortiz de Montellano, P. R. (2004). J. Med. Chem. 47, 3572-3579.

organic compounds