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Volume 69 
Part 1 
Page o64  
January 2013  

Received 16 November 2012
Accepted 3 December 2012
Online 8 December 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.044
wR = 0.132
Data-to-parameter ratio = 17.9
Details
Open access

2-Hydroxy-4-(prop-2-ynyloxy)benzaldehyde

aChemistry Research Centre, National Engineering College, K.R. Nagar, Kovilpatti 628 503, India, and bCAS in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai-25, India
Correspondence e-mail: drmaneelakantan@gmail.com

The asymmetric unit of the title compound, C10H8O3, contains two independent molecules, both of which are almost planar (r.m.s deviations for all non-H atoms of 0.044 and 0.053 Å). The dihedral angles between the benzene ring and the prop-1-yne group are 3.47 (1) and 3.07 (1)° in the two molecules, and the prop-1-yne groups adopt extended conformations. In each molecule, an intramolecular O-H...O hydrogen bond involving the OH and aldehyde substituents forms an S(6) ring. In the crystal, molecules are linked into cyclic centrosymmetric dimers via C-H...O hydrogen bonds, generating R22(14) ring motifs. The crystal structure is further stabilized by aromatic [pi]-[pi] stacking interactions between the benzene rings [centroid-centroid distances = 3.813 (2) and 3.843 (2) Å]

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 standard bond lengths, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]) and for hydrogen-bond motifs, 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
  • C10H8O3

  • Mr = 176.16

  • Triclinic, [P \overline 1]

  • a = 7.0835 (5) Å

  • b = 10.4059 (7) Å

  • c = 12.8461 (8) Å

  • [alpha] = 73.910 (3)°

  • [beta] = 89.756 (4)°

  • [gamma] = 73.436 (4)°

  • V = 869.16 (10) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 293 K

  • 0.20 × 0.20 × 0.20 mm

Data collection
  • Bruker SMART APEXII area-detector diffractometer

  • 15699 measured reflections

  • 4347 independent reflections

  • 2880 reflections with I > 2[sigma](I)

  • Rint = 0.029

Refinement
  • R[F2 > 2[sigma](F2)] = 0.044

  • wR(F2) = 0.132

  • S = 1.05

  • 4347 reflections

  • 243 parameters

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

  • [Delta][rho]max = 0.15 e Å-3

  • [Delta][rho]min = -0.20 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O2-H2...O3 0.82 1.92 2.6387 (16) 146
O5-H5...O6 0.82 1.93 2.6441 (16) 146
C10-H10...O3i 0.86 (2) 2.51 (2) 3.369 (2) 171.4 (2)
C18-H18A...O5ii 0.97 2.45 3.281 (2) 144
C20-H20...O6i 0.91 (2) 2.37 (2) 3.280 (2) 178.8 (2)
Symmetry codes: (i) x, y, z+1; (ii) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2 and SAINT. 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 (Farrugia, 2012)[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]; 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: SJ5285 ).


Acknowledgements

VS and DV thank the TBI X-ray facility, CAS in Crystallography and Biophysics, University of Madras, India, for the data collection and the UGC SAP for the facilities provided to the department.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bruker (2008). APEX2 and SAINT. 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] [details]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Ley, J. P. & Bertram, H. J. (2001). Bioorg. Med. Chem. Lett. 9, 1879-1885.  [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Zhao, X., Song, D. K., Radbil, A. B. & Radbil, B. A. (2007). Russ. J. Appl. Chem. 80, 1373-1375.  [ISI] [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o64  [ doi:10.1107/S1600536812049598 ]

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