7-Meth­oxy-2-phenyl­chroman-4-one

Agata Piaskowska; Maciej Hodorowicz; Wojciech Nitek

doi:10.1107/S1600536813001451

. 2013 Jan 23;69(Pt 2):o271. doi: 10.1107/S1600536813001451

7-Methoxy-2-phenylchroman-4-one

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

PMCID: PMC3569799 PMID: 23424545

Abstract

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 π–π [centroid–centroid distance = 3.912 (1) Å] and C—H⋯π 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-Susłow et al. (2010 ▶). For classification of X—H⋯π interactions, see: Malone et al. (1997 ▶). graphic file with name e-69-0o271-scheme1.jpg

Experimental

Crystal data

C₁₆H₁₄O₃
M _r = 254.27
Monoclinic,
a = 8.5600 (3) Å
b = 6.6320 (2) Å
c = 23.4130 (7) Å
β = 90.742 (2)°
V = 1329.04 (7) Å³
Z = 4
Mo Kα radiation
μ = 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 > 2σ(I)
R _int = 0.072

Refinement

R[F ² > 2σ(F ²)] = 0.086
wR(F ²) = 0.280
S = 1.18
2710 reflections
165 parameters
122 restraints
H-atom parameters constrained
Δρ_max = 0.65 e Å⁻³
Δρ_min = −0.35 e Å⁻³

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 Material

Click here for additional data file.^{(21KB, cif)}

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813001451/kj2213sup1.cif

e-69-0o271-sup1.cif^{(21KB, cif)}

Click here for additional data file.^{(130.4KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813001451/kj2213Isup2.hkl

e-69-0o271-Isup2.hkl^{(130.4KB, hkl)}

Click here for additional data file.^{(5.1KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813001451/kj2213Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

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

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) .

Acknowledgments

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

supplementary crystallographic information

Comment

Flavanones are of interest because of their anticancer effect as the aromatase inhibitors. By competing with androgens for binding with aromatase these compounds prevent the hydroxylation of C18 androgens to aromatic C19 estrogenic steroids (Hong & Chen, 2006). This suppresses the overexpression of aromatase in breast cancer (Pouget et al., 2001).

The heterocyclic ring contains O1, C2 and C3 atoms exhibiting static disorder. This disorder is propagated into the attached phenyl. The dihedral angle between the C5—C10 aromatic ring plane and the phenyl ring plane is 88.6 (1)° for the major disorder component (C11A—C16A) and 87.3 (1)° for the minor component (C11B—C16B). The structure is stabilized by π–π and C—H···π interactions (Table 1). The C5—C10 ring displays a π–π interaction with the C5ⁱ—C10ⁱ ring (Fig. 2 b) with a perpendicular distance of 3.543 (1) Å, a centroid-to-centroid distance of 3.912 (1) Å and a slippage of 1.658 Å [symmetry code: (i) 1 - x, -y, -z]. There are three types of C—H···π interactions: C13A—H13A···Cg4ⁱ (C13B—13B··· Cg4ⁱ in the minor disorder component), C19—H19B··· Cg4ⁱⁱ (Fig. 2a) and C15B—H15B···Cg3ⁱⁱⁱ (Fig. 2 a) [symmetry codes: (i) -x, y+1/2, 1/2-z, (ii) 1 - x, 1 - y, -z, (iii) x - 1, y, z]. The first interaction falls into type III X—H···pi interactions while the rest can be classified as type I according to Malone and coworkers (Malone et al. (1997)).

Experimental

The title compound was purchased from Sigma-Aldrich and used without further purification. Single crystals were obtained by slow evaporation of MeOH solution.