8-Acetyl-4-methyl-2-oxo-2H-chromen-7-yl acetate

Shu-Ping Yang; Li-Jun Han; Xin-Ran He; Li-Juan Chen

doi:10.1107/S1600536811048835

. 2011 Nov 19;67(Pt 12):o3382. doi: 10.1107/S1600536811048835

8-Acetyl-4-methyl-2-oxo-2H-chromen-7-yl acetate

Shu-Ping Yang ^a,^*, Li-Jun Han ^b, Xin-Ran He ^a, Li-Juan Chen ^a

PMCID: PMC3239025 PMID: 22199873

Abstract

In the title compound, C₁₄H₁₂O₅, the benzopyran-2-one ring system is approximately planar [maximum deviation = 0.018 (1) Å]; the mean plane is oriented at dihedral angles of 52.26 (11) and 72.92 (7)°, respectively, to the acetyl and acetoxy groups. In the crystal, π–π stacking is observed between parallel benzene rings of adjacent molecules, the centroid–centroid distance being 3.6774 (17) Å. Intermolecular weak C—H⋯O hydrogen bonding, and C=O⋯C=O [O⋯C = 3.058 (3) Å] and C=O⋯π [O⋯centroid = 3.328 (2) Å] interactions occur in the crystal structure.

Related literature

For structures of related coumarin derivatives, see: Yang et al. (2006 ▶, 2007 ▶, 2010 ▶).

Experimental

Crystal data

C₁₄H₁₂O₅
M _r = 260.24
Triclinic,
a = 8.198 (3) Å
b = 8.504 (3) Å
c = 9.644 (3) Å
α = 90.213 (4)°
β = 97.761 (4)°
γ = 111.686 (4)°
V = 618.0 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 298 K
0.30 × 0.10 × 0.10 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T _min = 0.969, T _max = 0.989
4891 measured reflections
2292 independent reflections
1572 reflections with I > 2σ(I)
R _int = 0.030

Refinement

R[F ² > 2σ(F ²)] = 0.048
wR(F ²) = 0.150
S = 1.07
2292 reflections
175 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg & Berndt, 1999 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811048835/xu5385sup1.cif

e-67-o3382-sup1.cif^{(21.4KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811048835/xu5385Isup2.hkl

e-67-o3382-Isup2.hkl^{(110.3KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811048835/xu5385Isup3.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
C6—H6⋯O2ⁱ	0.93	2.52	3.324 (3)	145

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Symmetry code: (i) Inline graphic .

Acknowledgments

The project was supported by the Natural Science Foundation of Huaihai Institute of Technology, China (No. Z2009019)

supplementary crystallographic information

Comment

Previous we have reported the crystal structures of some coumarin derivatives (Yang et al., 2006, 2007, 2010). As part of our study of the crystal structures of coumarin derivatives, we decribed here the crystal structure of 8-acetyl-7-acetoxy-4-methyl-2H-1-benzopyran-2-one, (I).

In the molecule (I) (Fig. 1), the benzopyran-2-one ring system is approximately palnar [maximum deviation 0.018 (1) Å]; the mean plane is oriented with respect to the acetyl and acetoxy groups at 52.26 (11) and 72.92 (7)°, respectively.

Molecules are linked together by one weak C—H···O hydrogen bond (Table. 1), two C═O···C═O interactions: C1═O2···C13ⁱⁱ═O4ⁱⁱ [O2···C13ⁱⁱ = 3.101 (3) Å, C1═O2···C13ⁱⁱ = 143.37 (15)°; symmetry code:(ii). x + 1, y + 1, z] and C1═O2···C1ⁱⁱⁱ═ O2ⁱⁱⁱ [O2···C1ⁱⁱⁱ = 3.058 (3) Å, C1═O2···C1ⁱⁱⁱ = 88.63 (13)°; symmetry code: (iii). 1 - x, 2 - y, 2 - z.], one C═ O···π interaction C1═O2···Cg1ⁱⁱⁱ [O2···Cg1ⁱⁱⁱ = 3.328 (2) Å, C1═O2···Cg1ⁱⁱⁱ = 113.74 (14)°, Cg1 is the centroid of the pyran ring] and one π-π stacking interaction Cg2···Cg2^iv [Cg2···Cg2^iv = 3.6774 (17) Å, Cg2 is the centroid of the benzene ring; symmetry code: (iv) -x, 1 - y, 2 - z] and generated a two-dimensional crystal structure by translation and inversion symmetry.

Experimental

To a solution containing 8-acetyl-7-hydroxy- 4-methylcoumarin (2.18 g, 10 mmol) and anhydrous pyridine (10 ml), a solution of acetic anhydride (1.53 g, 15 mmol) was slowly added at 278–283 K, with stirring, then the reaction mixture was stirred at 303 K continuously for 24 h and then poured into ice–water (200 ml). The solid obtained was filtered off, washed with water and dried at room temperature. Colourless crystal suitable for X-ray structure analysis were obtained by recrystallizing the crude product from an ethanol solution [m.p. 484–485K].