7-Hy­droxy-4-methyl-8-(3-methyl­benzo­yl)-2H-chromen-2-one ethanol monosolvate

Shu-Ping Yang; Li-Jun Han; Xiao-Yun Chen; Zhuan Gao

doi:10.1107/S1600536811046630

. 2011 Nov 9;67(Pt 12):o3253. doi: 10.1107/S1600536811046630

7-Hydroxy-4-methyl-8-(3-methylbenzoyl)-2H-chromen-2-one ethanol monosolvate

Shu-Ping Yang ^a,^*, Li-Jun Han ^b, Xiao-Yun Chen ^a, Zhuan Gao ^a

PMCID: PMC3238909 PMID: 22199762

Abstract

In the title compound, C₁₈H₁₄O₄·C₂H₆O, the coumarin ring system is approximately planar with a maximum deviation of 0.037 (3) Å and is nearly perpendicular to the benzene ring, making a dihedral angle of 86.55 (9)°. In the crystal, molecules are linked by classical O—H⋯O hydrogen bonds and weak C—H⋯O interactions.

Related literature

For the biological activity of coumarins, see: Sharma et al. (2005 ▶); Xiao et al. (2010 ▶); Iqbal et al. (2009 ▶); Siddiqui et al. (2009 ▶); Rollinger et al. (2004 ▶); Brühlmann et al. (2001 ▶). For a related structure, see: Yang et al. (2010 ▶).

Experimental

Crystal data

C₁₈H₁₄O₄·C₂H₆O
M _r = 340.36
Monoclinic,
a = 12.4562 (6) Å
b = 10.0341 (5) Å
c = 14.8999 (7) Å
β = 111.980 (3)°
V = 1726.93 (14) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.30 × 0.25 × 0.20 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T _min = 0.972, T _max = 0.982
12216 measured reflections
3021 independent reflections
1762 reflections with I > 2σ(I)
R _int = 0.119

Refinement

R[F ² > 2σ(F ²)] = 0.057
wR(F ²) = 0.188
S = 1.05
3021 reflections
229 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.25 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/S1600536811046630/xu5373sup1.cif

e-67-o3253-sup1.cif^{(25.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811046630/xu5373Isup2.hkl

e-67-o3253-Isup2.hkl^{(145.3KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811046630/xu5373Isup3.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
O3—H3⋯O5ⁱ	0.82	1.82	2.629 (3)	166
O5—H5A⋯O2	0.82	1.95	2.764 (3)	169
C17—H17⋯O2ⁱⁱ	0.93	2.54	3.398 (4)	154
C20—H20B⋯O4ⁱⁱⁱ	0.96	2.53	3.489 (5)	177

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

Acknowledgments

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

supplementary crystallographic information

Comment

Coumarins are very well known for their biological activity, such as antioxidants (Sharma et al., 2005), anticancer activity (Xiao et al., 2010), antiamoebic (Iqbal et al., 2009), anticonvulsant activity (Siddiqui et al., 2009) and inhibitions of acetylcholinesterase and monoamine oxidase (Rollinger et al., 2004; Brühlmann et al., 2001). Previous we have decribed the crystal structure of 8-benzoyl-7-hydroxy-4-methyl coumarin (Yang et al., 2010). As part of our study of the crystal structures of coumarin derivatives with 7-hydroxy, we report here the crystal structure of 8-(3-methylbenzoyl)-7-hydroxy-4-methyl-2H-1-benzopyran-2-one, (I).

In the molecule (I), the asymmetric unit contains one coumarin molecule and one ethanol molecule, and which are linked together by one O—H···O hydrogen bond (Table 1 and Fig. 1). The coumarin moiety (r.m.s deviations 0.0214 Å) and phenyl ring are perpendicular to each other with a dihedral angle of 86.55 (9)° between the plane of the atoms O1—O3/C1—C9 and the plane of C12—C17.

In crystal structure of (I), atom O3 in the molecule at (x, y, z) acts as hydrogen bond donor to atom O5 in the molecule at (x, y - 1, z), forming a C(10) chain running parallel to the [010] direction and generated by translation. Inversionally related molecular chains are linked together by a weak π–π interaction, the ring centroid Cg1[O1/C1—C4/C9] in the molecule at (x, y, z) connects Cg1 in the molecule at (1 - x, 1 - y, 1 - z) [centroid–centroid distance = 3.57278 (17) Å], so forming a doubled chain of R₄⁴(22) ring parallel to the [010] direction (Fig. 2). Neighboring doubled chains are linked into three-dimensional crystal structure by weak C—H···O hydrogen bonds (Table.1).

Experimental

The mixture containing 1.47 g (5 mmol) of dry powdered 7-(3-methylbenzoxy)-4-methylcoumarin and 2.0 g (15 mmol) of anhydrous aluminium chloride was heated for about 2 h at 463 K in an oil bath, then 30 ml of dilute (1:7) hydrochloric acid is added and the mixture is heated on a steam bath for 60 min, the crude products were filtered off, washed with water. Single crystals of (I) suitable for X-ray structure analysis were obtained by recrystallizing the crude product from a 95% ethanol solution, m.p. 503–504 K.