7-Meth­oxy-2-phenyl­chroman-4-one

Piaskowska, A.; Hodorowicz, M.; Nitek, W.

doi:10.1107/S1600536813001451

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 (C-C) = 0.006 Å
Disorder in main residue
R = 0.086
wR = 0.280
Data-to-parameter ratio = 16.4
Details

7-Methoxy-2-phenylchroman-4-one

Agata Piaskowska,^a ^* Maciej Hodorowicz ^a and Wojciech Nitek ^a

^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). For the properties of 7-methoxyflavanone, see: Pouget et al. (2001); Le Bail et al. (1998); Kostrzewa-Suslow et al. (2010). For classification of X-H [pi] interactions, see: Malone et al. (1997).

Experimental

Crystal data

C₁₆H₁₄O₃
M_r = 254.27
Monoclinic, P 2₁ /c
a = 8.5600 (3) Å
b = 6.6320 (2) Å
c = 23.4130 (7) Å
= 90.742 (2)°
V = 1329.04 (7) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.954, T_max = 0.991
15170 measured reflections
2710 independent reflections
1765 reflections with I > 2(I)
R_int = 0.072

Refinement

R[F² > 2(F²)] = 0.086
wR(F²) = 0.280
S = 1.18
2710 reflections
165 parameters
122 restraints
H-atom parameters constrained
_max = 0.65 e Å^-3
_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-HA	D-H	HA	DA	D-HA
C13A-H13ACg4ⁱ	0.93	2.80	3.598 (11)	144
C13A-H13ACg5ⁱ	0.93	2.71	3.515 (11)	146
C13B-H13BCg4ⁱ	0.93	2.82	3.695 (12)	158
C13B-H13BCg5ⁱ	0.93	2.76	3.639 (13)	157
C19-H19BCg4ⁱⁱ	0.96	2.72	3.619 (7)	156
C19-H19BCg5ⁱⁱ	0.96	2.76	3.660 (7)	157
C15B-H15BCg3ⁱⁱⁱ	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); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012); software used to prepare material for publication: publCIF (Westrip, 2010).

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.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Hong, Y. & Chen, S. (2006). Ann. N. Y. Acad. Sci. 1089, 237-251.
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.
Malone, J. F., Murray, C. M., Charlton, M. H., Docherty, R. & Lavery, A. J. (1997). J. Chem. Soc. Faraday Trans. 93, 3429-3436.
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.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.

organic compounds