(E)-1-(5-Hy­droxy-2,2-dimethyl-2H-chromen-6-yl)-3-(3,4,5-trimeth­oxy­phen­yl)prop-2-en-1-one

Guang-cheng Wang; Ying-hong Yang

doi:10.1107/S1600536811015236

. 2011 Apr 29;67(Pt 5):o1265. doi: 10.1107/S1600536811015236

(E)-1-(5-Hydroxy-2,2-dimethyl-2H-chromen-6-yl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one

Guang-cheng Wang ^a,^*, Ying-hong Yang ^b

PMCID: PMC3089353 PMID: 21754552

Abstract

The title compound, C₂₃H₂₄O₆, crystallizes with two independent molecules (A and B) in the asymmetric unit. The dihedral angles between the benzopyran ring and the α,β-unsaturated ketone unit and between the α,β-unsaturated ketone group and the benzene ring are 9.4 (10) and 12.96 (13)°, respectively, in molecule A and 1.40 (17) and 4.44 (17)°, respectively, in molecule B. The two methoxy groups at the meta positions of the benzene ring are close to being coplanar with the ring [C—O—C—C = 6.2 (3) and −1.4 (3)° in molecule A and −4.2 (4) and 3.7 (3)° in molecule B], whereas the third methoxy group, at the para position, is (+)-anticlinal with respect to the benzene ring [C—O—C—C = 81.7 (3)°] in molecule A and is (−)-synclinal with respect to the benzene ring [C—O—C—C = −103.2 (3)°] in molecule B. In both independent molecules, the hydroxy group is involved in an intramolecular O—H⋯O hydrogen bond.

Related literature

For the synthesis of related compounds, see: Krohn et al. (2002 ▶). For the biological activity of related compounds, see: Tran et al. (2009 ▶); Nerya et al. (2004 ▶). For related structures, see: Ranjith et al. (2010 ▶); Jasinski et al. (2009 ▶, 2010 ▶); Fun et al.(2010 ▶); Asiri et al.(2010 ▶).

Experimental

Crystal data

C₂₃H₂₄O₆
M _r = 396.42
Triclinic,
a = 9.9470 (9) Å
b = 13.9419 (13) Å
c = 16.1187 (11) Å
α = 72.681 (7)°
β = 89.487 (7)°
γ = 73.173 (8)°
V = 2035.3 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.22 × 0.15 × 0.15 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T _min = 0.952, T _max = 1.0
17082 measured reflections
8314 independent reflections
5047 reflections with I > 2σ(I)
R _int = 0.025

Refinement

R[F ² > 2σ(F ²)] = 0.057
wR(F ²) = 0.148
S = 1.01
8314 reflections
541 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Data collection: CrysAlis PRO (Oxford Diffraction,2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811015236/fl2342sup1.cif

e-67-o1265-sup1.cif^{(29KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811015236/fl2342Isup2.hkl

e-67-o1265-Isup2.hkl^{(406.7KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811015236/fl2342Isup3.cml

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O3	0.91 (3)	1.67 (3)	2.509 (2)	152 (3)
O8—H8⋯O9	0.98 (3)	1.64 (3)	2.536 (2)	149 (3)

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Acknowledgments

The authors thank Mr Zhi-Hua Mao of Sichuan University for the X-ray data collection.

supplementary crystallographic information

Comment

Chalcones (1,3-diaryl-2-propen-1-one) are natural or synthetic flavonoids displaying an impressive array of biological properties (Tran et al., 2009; Nerya et al.,2004). The title compound, (I), is one of our synthetic chalcone derivatives which have shown anti-inflammation activity. The crystal structures of related compounds: (E)-1-[4-(Prop-2-yn-1-yloxy)phenyl]-3- (3,4,5-trimethoxyphenyl)prop-2-en-1-one (Ranjith et al., 2010), (2E)-1-(2-Bromophenyl)-3- (3,4,5-trimethoxyphenyl)prop-2-en-1-one (Jasinski et al., 2010), (E)-1-(2-Furyl)-3- (3,4,5-trimethoxyphenyl)prop-2-en-1-one (Fun et al., 2010), (2E)-1-(4-fluorophenyl)-3- (3,4,5-trimethoxyphenyl)prop-2-en-1-one (Jasinski et al., 2009), and (2E)-1-(2,5-Dimethyl-3- thienyl)-3-(2-methoxyphenyl)prop-2-en-1-one (Asiri et al., 2010) have been reported. We report here the crystal structure of (I), a new chalcone.

(I) crystallizes with two independent molecules (A and B) in the asymmetric unit (Fig. 1). In one molecule, the dihedral angles between the benzopyran ring and the α,β-unsaturated ketone unit and between the α,β-unsaturated ketone group and the benzene ring are 9.42 (99) and 12.96 (13)°. The two methoxy groups at the meta positions of the benzene ring are close to being coplanar with the ring [C—O—C—C = 6.2 (3) and -1.4 (3)°], whereas the third methoxy group, at the para position, is (+)-anticlinal with respect to the benzene ring [C—O—C—C = 81.7 (3)°]. In the second molecule, the dihedral angles between the benzopyran ring and the α,β-unsaturated ketone unit and between the α,β-unsaturated ketone group and the benzene ring are 1.40 (17) and 4.44 (17)°. The two methoxy groups at the meta positions of the benzene ring are also close to being coplanar with the ring [C—O—C—C = -4.2 (4) and 3.7 (3)°], whereas the third methoxy group, at the para position, is (-)-synclinal with respect to the benzene ring [C—O—C—C = -103.2 (3)°]. In both independent molecules, the hydroxy group is involved in an intramolecular O—H···O hydrogen bond.

The crystal packing is shown in Fig. 2.

Experimental

1-(5-hydroxy-2,2-dimethyl-2H-chromen-6-yl)ethanone(2.182 g,10 mmol), 3,4,5-trimethoxybenzaldehyde(1.962 g,10 mmol) in ethanol was added KOH (20% w/v aqueous solution) and the mixture was stirred at 273 K for 10 h. Then the crude product was recrystallized from ethanol to give (I). Single crystals suitable for X-ray structure determination were grown by slow evaporation of an ethyl ether solution of (II)) at room temperature.