4-(Prop-2-yn-1-yl­oxy)benzaldehyde

Doi, I.; Okuno, T.

doi:10.1107/S1600536812050866

Volume 69
Part 1
Page o125
January 2013

Received 10 December 2012
Accepted 14 December 2012
Online 22 December 2012

Key indicators
Single-crystal X-ray study
T = 93 K
Mean (C-C) = 0.002 Å
R = 0.037
wR = 0.101
Data-to-parameter ratio = 13.0
Details

4-(Prop-2-yn-1-yloxy)benzaldehyde

Ikue Doi ^a and Tsunehisa Okuno ^a ^*

^aDepartment of Material Science and Chemistry, Wakayama University, Sakaedani, Wakayama 640-8510, Japan
Correspondence e-mail: okuno@center.wakayama-u.ac.jp

In the title molecule, C₁₀H₈O₂, all non-H atoms are essentailly coplanar (r.m.s. deviation = 0.0192 Å), indicating an effective conjugation of the carbonyl group, the benzene ring and the lone pair of the propynyloxy O atom. In the crystal, [pi] - [pi] stacking interactions [centroid-centroid distance = 3.5585 (15) Å] connect molecules into inversion dimers which are linked by Csp-HO=C hydrogen bonds, forming a ladder-like structure.

Related literature

For related structures of 4-(prop-2-yn-1-yloxy)benzenes, see: Berscheid et al. (1992); Mohr et al. (2003); Nieger et al. (2004); Ranjith et al. (2010); Zhang et al. (2011).

Experimental

Crystal data

C₁₀H₈O₂
M_r = 160.17
Monoclinic, P 2₁ /n
a = 7.906 (3) Å
b = 7.385 (2) Å
c = 14.036 (5) Å
= 102.025 (5)°
V = 801.5 (5) Å³
Z = 4
Mo K radiation
= 0.09 mm^-1
T = 93 K
0.20 × 0.10 × 0.10 mm

Data collection

Rigaku Saturn724+ diffractometer
Absorption correction: numerical (NUMABS; Rigaku, 1999) T_min = 0.984, T_max = 0.991
6309 measured reflections
1832 independent reflections
1669 reflections with F² > 2(F²)
R_int = 0.044

Refinement

R[F² > 2(F²)] = 0.037
wR(F²) = 0.101
S = 1.06
1831 reflections
141 parameters
H-atom parameters constrained
_max = 0.32 e Å^-3
_min = -0.17 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C10-H10O1ⁱ	0.95	2.23	3.1575 (14)	166
Symmetry code: (i) $[x+{\script{3\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: CrystalClear (Rigaku, 2008); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXD (Schneider & Sheldrick, 2002); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012); software used to prepare material for publication: CrystalStructure (Rigaku, 2010).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5571 ).

Acknowledgements

This work was supported by the Research for Promoting Technological Seeds from the Japan Science and Technology Agency (JST).

References

Berscheid, R., Nieger, M. & Vogtle, F. (1992). Chem. Ber. 125, 2539-2552.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Mohr, F., Eisler, D. J., McArdle, C. P., Atieh, K., Jennings, M. C. & Puddephatt, R. J. (2003). J. Organomet. Chem. 670, 27-36.
Nieger, M., Michel, I. & Vogtle, F. (2004). Private communication (deposition number 246025). CCDC, Cambridge, England.
Ranjith, S., Thirunarayanan, A., Raja, S., Rajakumar, P. & SubbiahPandi, A. (2010). Acta Cryst. E66, o2261-o2262.
Rigaku (1999). NUMABS. Rigaku Corporation, Tokyo, Japan.
Rigaku (2008). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Rigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan.
Schneider, T. R. & Sheldrick, G. M. (2002). Acta Cryst. D58, 1772-1779.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Zhang, C.-H., Zhao, J.-M. & Chen, B.-G. (2011). Acta Cryst. E67, o150.

organic compounds