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Volume 69 
Part 2 
Page o271  
February 2013  

Received 7 October 2012
Accepted 15 January 2013
Online 23 January 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.006 Å
Disorder in main residue
R = 0.086
wR = 0.280
Data-to-parameter ratio = 16.4
Details
Open access

7-Methoxy-2-phenylchroman-4-one

aFaculty of Chemistry, Jagiellonian University, Ingardena 3, 30-060 Krakow, Poland
Correspondence e-mail: agata.piaskowska@uj.edu.pl

In the title compound, C16H14O3, the ring O atom and the two adjacent non-fused C atoms, as well as the attached phenyl ring, exhibit static disorder [occupancy ratio 0.559 (12):0.441 (12)]. The crystal packing features [pi]-[pi] [centroid-centroid distance = 3.912 (1) Å] and C-H...[pi] interactions.

Related literature

For aromatase inhibition of flavanones, see: Hong & Chen (2006[Hong, Y. & Chen, S. (2006). Ann. N. Y. Acad. Sci. 1089, 237-251.]). For the properties of 7-methoxyflavanone, see: Pouget et al. (2001[Pouget, C., Lauthier, F., Simon, A., Fagnere, C., Basly, J.-P., Delage, C. & Chulia, A.-J. (2001). Bioorg. Med. Chem. Lett. 11, 3095-3097.]); Le Bail et al. (1998[Le Bail, J. C., Varnat, F., Nicolas, J. C. & Habrioux, G. (1998). Cancer Lett., 130, 209-216.]); Kostrzewa-Suslow et al. (2010[Kostrzewa-Suslow, E., Dmochowska-Gladysz, J. & Janeczko, T. (2010). Z. Naturforsch. Teil C, 65, 55-60.]). For classification of X-H...[pi] interactions, see: Malone et al. (1997[Malone, J. F., Murray, C. M., Charlton, M. H., Docherty, R. & Lavery, A. J. (1997). J. Chem. Soc. Faraday Trans. 93, 3429-3436.]).

[Scheme 1]

Experimental

Crystal data
  • C16H14O3

  • Mr = 254.27

  • Monoclinic, P 21 /c

  • a = 8.5600 (3) Å

  • b = 6.6320 (2) Å

  • c = 23.4130 (7) Å

  • [beta] = 90.742 (2)°

  • V = 1329.04 (7) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 293 K

  • 0.55 × 0.16 × 0.10 mm

Data collection
  • Nonius KappaCCD diffractometer

  • Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]) Tmin = 0.954, Tmax = 0.991

  • 15170 measured reflections

  • 2710 independent reflections

  • 1765 reflections with I > 2[sigma](I)

  • Rint = 0.072

Refinement
  • R[F2 > 2[sigma](F2)] = 0.086

  • wR(F2) = 0.280

  • S = 1.18

  • 2710 reflections

  • 165 parameters

  • 122 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.65 e Å-3

  • [Delta][rho]min = -0.35 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg3, Cg4 and Cg5 are the centroids of the C5-C10, C11A-C16A and C11B-C16B rings, respectively.

D-H...A D-H H...A D...A D-H...A
C13A-H13A...Cg4i 0.93 2.80 3.598 (11) 144
C13A-H13A...Cg5i 0.93 2.71 3.515 (11) 146
C13B-H13B...Cg4i 0.93 2.82 3.695 (12) 158
C13B-H13B...Cg5i 0.93 2.76 3.639 (13) 157
C19-H19B...Cg4ii 0.96 2.72 3.619 (7) 156
C19-H19B...Cg5ii 0.96 2.76 3.660 (7) 157
C15B-H15B...Cg3iii 0.93 2.65 3.497 (14) 151
Symmetry codes: (i) [-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) -x+1, -y+1, -z; (iii) x-1, y, z.

Data collection: COLLECT (Nonius, 1998[Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: SCALEPACK (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: DENZO (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]) and SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1994[Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.]); 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: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: KJ2213 ).


Acknowledgements

The authors thank the Joint X-ray Laboratory, Faculty of Chemistry, Jagiellonian University, for making the Nonius KappaCCD diffractometer available.

References

Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.  [CrossRef] [details]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Hong, Y. & Chen, S. (2006). Ann. N. Y. Acad. Sci. 1089, 237-251.  [ISI] [CrossRef] [PubMed] [ChemPort]
Kostrzewa-Suslow, E., Dmochowska-Gladysz, J. & Janeczko, T. (2010). Z. Naturforsch. Teil C, 65, 55-60.
Le Bail, J. C., Varnat, F., Nicolas, J. C. & Habrioux, G. (1998). Cancer Lett., 130, 209-216.  [ISI] [CrossRef] [ChemPort] [PubMed]
Malone, J. F., Murray, C. M., Charlton, M. H., Docherty, R. & Lavery, A. J. (1997). J. Chem. Soc. Faraday Trans. 93, 3429-3436.  [CrossRef] [ChemPort]
Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.
Pouget, C., Lauthier, F., Simon, A., Fagnere, C., Basly, J.-P., Delage, C. & Chulia, A.-J. (2001). Bioorg. Med. Chem. Lett. 11, 3095-3097.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o271  [ doi:10.1107/S1600536813001451 ]

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