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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 [sigma](C-C) = 0.002 Å
R = 0.037
wR = 0.101
Data-to-parameter ratio = 13.0
Details
Open access

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

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-H...O=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[Berscheid, R., Nieger, M. & Vogtle, F. (1992). Chem. Ber. 125, 2539-2552.]); Mohr et al. (2003[Mohr, F., Eisler, D. J., McArdle, C. P., Atieh, K., Jennings, M. C. & Puddephatt, R. J. (2003). J. Organomet. Chem. 670, 27-36.]); Nieger et al. (2004[Nieger, M., Michel, I. & Vogtle, F. (2004). Private communication (deposition number 246025). CCDC, Cambridge, England.]); Ranjith et al. (2010[Ranjith, S., Thirunarayanan, A., Raja, S., Rajakumar, P. & SubbiahPandi, A. (2010). Acta Cryst. E66, o2261-o2262.]); Zhang et al. (2011[Zhang, C.-H., Zhao, J.-M. & Chen, B.-G. (2011). Acta Cryst. E67, o150.]).

[Scheme 1]

Experimental

Crystal data
  • C10H8O2

  • Mr = 160.17

  • Monoclinic, P 21 /n

  • a = 7.906 (3) Å

  • b = 7.385 (2) Å

  • c = 14.036 (5) Å

  • [beta] = 102.025 (5)°

  • V = 801.5 (5) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[Rigaku (1999). NUMABS. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.984, Tmax = 0.991

  • 6309 measured reflections

  • 1832 independent reflections

  • 1669 reflections with F2 > 2[sigma](F2)

  • Rint = 0.044

Refinement
  • R[F2 > 2[sigma](F2)] = 0.037

  • wR(F2) = 0.101

  • S = 1.06

  • 1831 reflections

  • 141 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.32 e Å-3

  • [Delta][rho]min = -0.17 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C10-H10...O1i 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[Rigaku (2008). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXD (Schneider & Sheldrick, 2002[Schneider, T. R. & Sheldrick, G. M. (2002). Acta Cryst. D58, 1772-1779.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: CrystalStructure (Rigaku, 2010[Rigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan.]).


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.  [CrossRef] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Mohr, F., Eisler, D. J., McArdle, C. P., Atieh, K., Jennings, M. C. & Puddephatt, R. J. (2003). J. Organomet. Chem. 670, 27-36.  [CrossRef] [ChemPort]
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.  [CSD] [CrossRef] [ChemPort] [details]
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.  [ISI] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Zhang, C.-H., Zhao, J.-M. & Chen, B.-G. (2011). Acta Cryst. E67, o150.  [CrossRef] [details]


Acta Cryst (2013). E69, o125  [ doi:10.1107/S1600536812050866 ]

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