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Volume 70 
Part 1 
Page o24  
January 2014  

Received 18 November 2013
Accepted 30 November 2013
Online 7 December 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.043
wR = 0.130
Data-to-parameter ratio = 17.8
Details
Open access

1-[2-Hy­droxy-4-(prop-2-yn-1-yl­oxy)phen­yl]ethanone

aChemistry Research Centre, National Engineering College, K.R. Nagar, Kovilpatti 628 503, India, and bCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India
Correspondence e-mail: drmaneelakantan@gmail.com

In the title compound, C11H10O3, there is an intra­molecular O-H...O hydrogen bond generating an S(6) ring motif. The O atom of the hy­droxy group deviates by 0.0200 (1) Å from the benzene ring to which it is attached. The propyne group is almost linear, the C-C[triple bond]C angle being 177.83 (15)°, and is almost coplanar with the benzene ring; the C-C-O-C torsion angle being only -1.1 (2)°. In the crystal, mol­ecules are linked via C-H...O hydrogen bonds, forming infinite C(11) chains running parallel to [103]. These chains are linked by a pair of C-H...O hydrogen bonds, enclosing R22(8) inversion dimers, forming a corrugated two-dimensional network lying parallel to (103).

Related literature

For the biological activity of benzaldehyde derivatives, see: Zhao et al. (2007[Zhao, X., Song, D. K., Radbil, A. B. & Radbil, B. A. (2007). Russ. J. Appl. Chem. 80, 1373-1375.]); Ley & Bertram (2001[Ley, J. P. & Bertram, H. J. (2001). Bioorg. Med. Chem. Lett. 9, 1879-1885.]); Delogu et al. (2010[Delogu, G., Podda, G., Corda, M., Fadda, M. B., Fais, A. & Era, B. (2010). Bioorg. Med. Chem. Lett. 20, 6138-6140.]). For a related structure, see: Esakkiammal et al. (2012[Esakkiammal, M., Selvarani, V., Neelakantan, M. A., Silambarasan, V. & Velmurugan, D. (2012). Acta Cryst. E68, o2465.]). For graph-set notation, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C11H10O3

  • Mr = 190.19

  • Monoclinic, P 21 /n

  • a = 4.9975 (2) Å

  • b = 10.4305 (4) Å

  • c = 18.8467 (7) Å

  • [beta] = 97.257 (2)°

  • V = 974.54 (7) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 293 K

  • 0.35 × 0.30 × 0.20 mm

Data collection
  • Bruker SMART APEXII area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.968, Tmax = 0.981

  • 9316 measured reflections

  • 2451 independent reflections

  • 1898 reflections with I > 2[sigma](I)

  • Rint = 0.021

Refinement
  • R[F2 > 2[sigma](F2)] = 0.043

  • wR(F2) = 0.130

  • S = 1.05

  • 2451 reflections

  • 138 parameters

  • 3 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.17 e Å-3

  • [Delta][rho]min = -0.21 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...O2 0.82 1.83 2.5551 (14) 146
C4-H4...O3i 0.93 2.54 3.4609 (16) 172
C11-H11...O2ii 0.93 2.32 3.2337 (18) 168
Symmetry codes: (i) -x+3, -y+2, -z; (ii) [x+{\script{3\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2668 ).


Acknowledgements

The authors thank the TBI X-ray facility and the UGC (SAP) CAS in Crystallography and Biophysics, University of Madras, India, for the data collection and other facilities. TS thanks the DST for an Inspire Fellowship.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [Web of Science]
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Delogu, G., Podda, G., Corda, M., Fadda, M. B., Fais, A. & Era, B. (2010). Bioorg. Med. Chem. Lett. 20, 6138-6140.  [CrossRef] [ChemPort] [PubMed]
Esakkiammal, M., Selvarani, V., Neelakantan, M. A., Silambarasan, V. & Velmurugan, D. (2012). Acta Cryst. E68, o2465.  [CSD] [CrossRef] [IUCr Journals]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Ley, J. P. & Bertram, H. J. (2001). Bioorg. Med. Chem. Lett. 9, 1879-1885.  [CrossRef] [ChemPort]
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Zhao, X., Song, D. K., Radbil, A. B. & Radbil, B. A. (2007). Russ. J. Appl. Chem. 80, 1373-1375.  [Web of Science] [CrossRef] [ChemPort]


Acta Cryst (2014). E70, o24  [ doi:10.1107/S1600536813032613 ]

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