4,7,8-Trimethyl-2H-chromen-2-one

Jian-Xin Yang; Xue-Mei Tan; Xiang-Hui Wang; Yin Wang

doi:10.1107/S1600536812009646

. 2012 Mar 10;68(Pt 4):o1014. doi: 10.1107/S1600536812009646

4,7,8-Trimethyl-2H-chromen-2-one

Jian-Xin Yang ^a,^*, Xue-Mei Tan ^a, Xiang-Hui Wang ^b, Yin Wang ^a

PMCID: PMC3343979 PMID: 22589888

Abstract

The molecule of the title compound, C₁₂H₁₂O₂, is essentially planar, with a maximum deviation from the mean plane of all non-H atoms of 0.038 (1) Å for the methyl C atom in the 8-position. The crystal structure is characterized by antiparallel π–π stacking along the c axis, with centroid–centroid distances as short as 3.866 (1) Å. In the crystal, C—H⋯O hydrogen bonds connect the molecules across the stacks into ribbons in the a-axis direction.

Related literature

For general background to the pharmacological activity of coumarin derivatives, see: Xie et al. (2001 ▶); Tanitame et al. (2004 ▶); Shao et al. (1997 ▶); Rendenbach-Müller et al. (1994 ▶); Pochet et al. (1996 ▶). For a related structure, see: Gowda et al. (2010 ▶).

Experimental

Crystal data

C₁₂H₁₂O₂
M _r = 188.22
Monoclinic,
a = 7.276 (3) Å
b = 18.075 (6) Å
c = 7.246 (3) Å
β = 97.055 (5)°
V = 945.8 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 153 K
0.44 × 0.31 × 0.26 mm

Data collection

Rigaku AFC10/Saturn724+ diffractometer
8545 measured reflections
2747 independent reflections
2176 reflections with I > 2σ(I)
R _int = 0.028

Refinement

R[F ² > 2σ(F ²)] = 0.050
wR(F ²) = 0.112
S = 1.00
2747 reflections
130 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Data collection: CrystalClear (Rigaku, 2008 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: SHELXTL and publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812009646/ld2048sup1.cif

e-68-o1014-sup1.cif^{(14.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812009646/ld2048Isup2.hkl

e-68-o1014-Isup2.hkl^{(134.9KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812009646/ld2048Isup3.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
C2—H2⋯O2ⁱ	0.95	2.56	3.460 (2)	159
C10—H10C⋯O2ⁱⁱ	0.98	2.54	3.493 (2)	164

Open in a new tab

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

Acknowledgments

The authors are grateful to the National Natural Science Foundation of China (No. 20962007) and the Creative Talents Plan of the Hainan University 211 Project.

supplementary crystallographic information

Comment

Coumarin derivatives exhibit a wide variety of pharmacological activities including anti-HIV (Xie et al., 2001), antibacterial (Tanitame et al., 2004), antioxidant (Shao et al., 1997), antithrombotic (Rendenbach-Müller et al., 1994) and antiinflammatory (Pochet et al., 1996) activities.

The molecular structure is shown in Fig. 1. In the crystal the molecules are linked by C—H···O hydrogen bonds to form ribbon-like motives (Table 1 and Fig. 2).

Experimental

2,3-Dimethyl phenol (10.50 mmol) was slowly added at 278–288 K to a mixture of para-toluenesulfonic acid (0.5 g) and acetylacetic ester (10.50 mmol) while stirring for 30 min. The reaction mixture was stirred continuously for 12 more hours at room temperature and then poured into ice–water mixture (100 ml). The obtained solid was filtered off, washed with cold water and dried at room temperature. Colorless crystals of the title compound suitable for X-ray structure analysis were obtained by slow evaporation of a solution in the mixture of ethanol/ether over a period of two days.