(E)-N-[2-(Biphenyl-4-ylvin­yl)phen­yl]furan-2-carboxamide

Kee, C.H.; Thomas, N.F.; Ariffin, A.; Awang, K.; Ng, S.W.

doi:10.1107/S1600536808034569

Volume 64
Part 11
Page o2210
November 2008

Received 14 October 2008
Accepted 23 October 2008
Online 25 October 2008

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R = 0.039
wR = 0.106
Data-to-parameter ratio = 17.2
Details

(E)-N-[2-(Biphenyl-4-ylvinyl)phenyl]furan-2-carboxamide

Chin Hui Kee,^a Noel F. Thomas,^a Azhar Ariffin,^a Khalijah Awang ^a and Seik Weng Ng ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
Correspondence e-mail: seikweng@um.edu.my

In the title molecule, C₂₅H₁₉NO₂, the furyl ring is twisted by 46.3 (1)° with respect to the phenylene ring bearing the amido group. In the stilbene unit, the two phenylene rings (i.e. the rings connected through the -CH=CH- fragment) are twisted by 59.2 (1)°; in the biphenylene unit, the two benzene rings are twisted by 35.5 (1)°. In the crystal structure, molecules are linked by an N-HO_amido hydrogen bond into a zigzag chain running along the c axis.

Related literature

For the use of radical cations in heterocyclic synthesis, see: Thomas et al. (2004, 2008).

Experimental

Crystal data

C₂₅H₁₉NO₂
M_r = 365.41
Monoclinic, P 2₁ /c
a = 10.9271 (2) Å
b = 19.7960 (4) Å
c = 8.7969 (1) Å
= 92.374 (1)°
V = 1901.25 (6) Å³
Z = 4
Mo K radiation
= 0.08 mm^-1
T = 100 (2) K
0.40 × 0.35 × 0.15 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: none
13179 measured reflections
4356 independent reflections
3681 reflections with I > 2(I)
R_int = 0.022

Refinement

R[F² > 2(F²)] = 0.039
wR(F²) = 0.106
S = 1.04
4356 reflections
253 parameters
H-atom parameters constrained
_max = 0.30 e Å^-3
_min = -0.25 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1O2ⁱ	0.88	2.05	2.903 (1)	163
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); 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); software used to prepare material for publication: publCIF (Westrip, 2008).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH2714 ).

Acknowledgements

We thank the Ministry of Science, Technology & Innovation (MOSTI) for supporting this study; CHK thanks MOSTI for an NSF scholarship.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Thomas, N. F., Kee, C.-H., Ariffin, A., Awang, K., Weber, J.-F. F., Lim, C.-G., Mukhtar, M. R. & Abdul Hadi, A. H. (2008). Heterocycles, 75, 1097-1108.
Thomas, N. F., Velu, S. S., Weber, J.-F. F., Lee, K. C., Abdul Hadi, A. H., Richomme, P., Rondeau, D., Noorbatcha, I. & Awang, K. (2004). Tetrahedron, 51, 11733-11742.
Westrip, S. P. (2008). publCIF. In preparation.

organic compounds