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Volume 69 
Part 6 
Page o895  
June 2013  

Received 16 April 2013
Accepted 23 April 2013
Online 15 May 2013

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.002 Å
R = 0.040
wR = 0.107
Data-to-parameter ratio = 12.1
Details
Open access

2-(4-Hydroxyphenyl)-3-methoxy-4H-chromen-4-one

aInstitute of Chemistry, V.N. Karazin National University, Svobody 4, 61077 Kharkiv, Ukraine, and bFaculty of Chemistry, University of Gdansk, J. Sobieskiego 18, 80-952 Gdansk, Poland
Correspondence e-mail: bla@chem.univ.gda.pl

In the title compound, C16H12O4, the substituent benzene ring and methoxy group are twisted relative to the 4H-chromene skeleton by 24.1 (1) and 61.3 (1)°, respectively. In the crystal, molecules are connected by classical O-H...O and weak C-H...O hydrogen bonds, forming chains parallel to [201]. The 4H-chromene ring systems of adjacent molecules are either parallel or inclined at an angle of 28.9 (1)°.

Related literature

For general features of flavones and flavonols (derivatives of 3-hydroxy-2-phenyl-4H-chromen-4-one), see: Demchenko (2009[Demchenko, A. P. (2009). In Introduction to Fluorescence Sensing. The Netherlands: Springer Science and Business Media BV.]); Ma et al. (2012[Ma, J., Liu, Y., Chen, L., Xie, Y., Wang, L.-Y. & Xie, M.-X. (2012). Food Chem. 132, 663-670.]). For related structures, see: Wera et al. (2011a[Wera, M., Pivovarenko, V. G. & Blazejowski, J. (2011a). Acta Cryst. E67, o264-o265.],b[Wera, M., Serdiuk, I. E., Roshal, A. D. & Blazejowski, J. (2011b). Acta Cryst. E67, o440.]). For intermolecular interactions, see: Aakeröy et al. (1992[Aakeröy, C. B., Seddon, K. R. & Leslie, M. (1992). Struct. Chem. 3, 63-65.]); Etter et al. (1990[Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.]); Novoa et al. (2006[Novoa, J. J., Mota, F. & D'Oria, E. (2006). Hydrogen Bonding - New Insights, edited by S. Grabowski, pp. 193-244. The Netherlands: Springer.]). For the synthesis, see: Bader et al. (2003[Bader, A. N., Pivovarenko, V., Demchenko, A. P., Ariese, F. & Gooijer, C. (2003). Spectrochim. Acta Part A, 59, 1593-1603.]); Wera et al. (2011b[Wera, M., Serdiuk, I. E., Roshal, A. D. & Blazejowski, J. (2011b). Acta Cryst. E67, o440.]).

[Scheme 1]

Experimental

Crystal data
  • C16H12O4

  • Mr = 268.26

  • Monoclinic, P 21 /c

  • a = 8.7191 (5) Å

  • b = 8.8978 (4) Å

  • c = 16.706 (1) Å

  • [beta] = 103.801 (6)°

  • V = 1258.65 (12) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 295 K

  • 0.6 × 0.45 × 0.25 mm

Data collection
  • Oxford Diffraction Gemini R Ultra Ruby CCD diffractometer

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.943, Tmax = 0.970

  • 5100 measured reflections

  • 2245 independent reflections

  • 1801 reflections with I > 2[sigma](I)

  • Rint = 0.021

Refinement
  • R[F2 > 2[sigma](F2)] = 0.040

  • wR(F2) = 0.107

  • S = 1.03

  • 2245 reflections

  • 185 parameters

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

  • [Delta][rho]max = 0.14 e Å-3

  • [Delta][rho]min = -0.18 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O20-H20...O12i 0.93 (3) 1.77 (3) 2.648 (2) 157 (2)
C7-H7...O20ii 0.93 2.56 3.337 (3) 141
Symmetry codes: (i) [x+1, -y-{\script{1\over 2}}, z+{\script{1\over 2}}]; (ii) [x-1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: CrysAlis CCD (Oxford Diffraction, 2008[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2008[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); 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.]; 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: XU5696 ).


Acknowledgements

This study was financed by the State Funds for Scientific Research (grant DS/530-8220-D184-3).

References

Aakeröy, C. B., Seddon, K. R. & Leslie, M. (1992). Struct. Chem. 3, 63-65.
Bader, A. N., Pivovarenko, V., Demchenko, A. P., Ariese, F. & Gooijer, C. (2003). Spectrochim. Acta Part A, 59, 1593-1603.
Demchenko, A. P. (2009). In Introduction to Fluorescence Sensing. The Netherlands: Springer Science and Business Media BV.
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.  [CrossRef] [ISI] [details]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Ma, J., Liu, Y., Chen, L., Xie, Y., Wang, L.-Y. & Xie, M.-X. (2012). Food Chem. 132, 663-670.  [ISI] [CrossRef] [ChemPort]
Novoa, J. J., Mota, F. & D'Oria, E. (2006). Hydrogen Bonding - New Insights, edited by S. Grabowski, pp. 193-244. The Netherlands: Springer.
Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]
Wera, M., Pivovarenko, V. G. & Blazejowski, J. (2011a). Acta Cryst. E67, o264-o265.  [CSD] [CrossRef] [ChemPort] [details]
Wera, M., Serdiuk, I. E., Roshal, A. D. & Blazejowski, J. (2011b). Acta Cryst. E67, o440.  [CSD] [CrossRef] [details]


Acta Cryst (2013). E69, o895  [ doi:10.1107/S1600536813010982 ]

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