(IUCr) 2-Phenylimidazo[1,2-a]pyridine-3-carbaldehyde

Volume 64
Part 5
Page o927
May 2008

Received 8 April 2008
Accepted 21 April 2008
Online 26 April 2008

Key indicators
Single-crystal X-ray study
T = 120 K
Mean (C-C) = 0.002 Å
R = 0.032
wR = 0.078
Data-to-parameter ratio = 14.3
Details

2-Phenylimidazo[1,2-a]pyridine-3-carbaldehyde

Abderrahman Anaflous,^a Hanane Albay,^a Nour-eddine Benchat,^a Brahim El Bali,^b Michal Dusek ^c and Karla Fejfarová ^c ^*

^aDépartement de Chimie, Faculté des Sciences, BP 717, 60000 Oujda, Morocco,^bLaboratory of Mineral Solid and Analytical Chemistry, `LMSAC', Department of Chemistry, Faculty of Sciences, University Mohamed I, PO Box 717, 60000 Oujda, Morocco, and ^cInstitute of Physics, Na Slovance 2, 182 21 Praha 8, Czech Republic
Correspondence e-mail: fejfarov@fzu.cz

In the title compound, C₁₄H₁₀N₂O, the dihedral angle between the imidazo[1,2-a]pyridine and phenyl rings is 28.61 (4)° The molecules are connected into broad chains parallel to the a axis by weak C-HO and C-HN hydrogen bonds. The linking of the ribbons is provided by [pi] - [pi] stacking interactions between neighbouring pyridine rings, with a centroid-centroid distance of 3.7187 (7) Å.

Related literature

For general background, see Anaflous et al. (2008) and references therein. For related literature, see: Meth-Cohn & Stanforth (1991).

Experimental

Crystal data

C₁₄H₁₀N₂O
M_r = 222.2
Orthorhombic, P b c a
a = 13.0640 (3) Å
b = 7.4162 (2) Å
c = 21.6698 (6) Å
V = 2099.48 (9) Å³
Z = 8
Mo K radiation
= 0.09 mm^-1
T = 120 K
0.57 × 0.40 × 0.24 mm

Data collection

Oxford Diffraction Xcalibur2 diffractometer with Sapphire2 CCD detector
Absorption correction: none
25795 measured reflections
2196 independent reflections
1305 reflections with I > 3(I)
R_int = 0.049

Refinement

R[F² > 2(F²)] = 0.031
wR(F²) = 0.077
S = 1.04
2196 reflections
154 parameters
H-atom parameters constrained
_max = 0.15 e Å^-3
_min = -0.16 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C4-H4N1ⁱ	0.96	2.50	3.4386 (18)	165
C6-H6O1ⁱⁱ	0.96	2.46	3.1856 (16)	133
Symmetry codes: (i) -x+1, -y, -z; (ii) -x, -y, -z.

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); data reduction: CrysAlis RED; program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: JANA2000 (Petrícek et al., 2000); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: JANA2000.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BG2180 ).

Acknowledgements

The Grant Agency of the Czech Republic is acknowledged for grant No 202/05/0757

References

Anaflous, A., Albay, H., Benchat, N., El Bali, B., Dusek, M. & Fejfarova, K. (2008). Acta Cryst. E64, o926.
Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Postfach 1251, D-53002 Bonn, Germany.
Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103.
Meth-Cohn, O. & Stanforth, S. P. (1991). Comp. Org. Synth. 2, 777-794.
Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.
Petrícek, V., Dusek, M. & Palatinus, L. (2000). JANA2000. Institute of Physics, Prague, Czech Republic.

organic compounds