8-Benzoyl-7-hy­droxy-4-methyl-2H-1-benzopyran-2-one monohydrate

Shu-Ping Yang; Li-Jun Han; Da-Qi Wang; Xiao-Yun Chen

doi:10.1107/S1600536810046350

. 2010 Nov 13;66(Pt 12):o3183. doi: 10.1107/S1600536810046350

8-Benzoyl-7-hydroxy-4-methyl-2H-1-benzopyran-2-one monohydrate

Shu-Ping Yang ^a,^*, Li-Jun Han ^b, Da-Qi Wang ^c, Xiao-Yun Chen ^a

PMCID: PMC3011619 PMID: 21589478

Abstract

In the title compound, C₁₇H₁₂O₄·H₂O, the coumarin ring system is approximately planar with a maximum atomic deviation of 0.011 (2) Å, and is nearly perpendicular to the phenyl ring at a dihedral angle of 86.63 (9)°. In the crystal, molecules are linked by classical O—H⋯O and weak C—H⋯O hydrogen bonds. π–π stacking is also present [centroid–centroid distance = 3.6898 (12) Å].

Related literature

For the biological activity of coumarins, see: Sharma et al. (2005 ▶); Iqbal et al. (2009 ▶); Siddiqui et al. (2009 ▶); Vyas et al. (2009 ▶); Rollinger et al. (2004 ▶); Brühlmann et al. (2001 ▶). For related structures, see: Yang et al. (2006 ▶, 2007 ▶, 2008 ▶).

Experimental

Crystal data

C₁₇H₁₂O₄·H₂O
M _r = 298.28
Monoclinic,
a = 14.8912 (15) Å
b = 9.6768 (11) Å
c = 20.644 (2) Å
β = 104.275 (2)°
V = 2882.9 (5) Å³
Z = 8
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 298 K
0.49 × 0.24 × 0.21 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.952, T _max = 0.979
7271 measured reflections
2549 independent reflections
1706 reflections with I > 2σ(I)
R _int = 0.036

Refinement

R[F ² > 2σ(F ²)] = 0.040
wR(F ²) = 0.110
S = 1.05
2549 reflections
255 parameters
All H-atom parameters refined
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810046350/xu5087sup1.cif

e-66-o3183-sup1.cif^{(16.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810046350/xu5087Isup2.hkl

e-66-o3183-Isup2.hkl^{(125.3KB, hkl)}

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	0.93 (3)	1.72 (3)	2.650 (2)	177 (3)
O5—H5A⋯O2	0.91 (4)	2.00 (4)	2.887 (3)	166 (3)
O5—H5B⋯O4ⁱⁱ	0.87 (3)	2.03 (3)	2.875 (2)	162 (3)
C17—H17⋯O2ⁱⁱⁱ	0.95 (2)	2.54 (2)	3.422 (3)	154.7 (16)

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

Acknowledgments

The authors acknowledge the financial support of the Huaihai Institute of Technology Science Foundation (No. KX10019).

supplementary crystallographic information

Comment

Coumarins are very well known for their biological activity, such as antioxidants (Sharma et al., 2005), antiamoebic (Iqbal et al., 2009), anticonvulsant activity (Siddiqui et al., 2009), antimicrobial (Vyas et al., 2009) and inhibitions of acetylcholinesterase and monoamine oxidase (Rollinger et al., 2004; Brühlmann et al., 2001). The crystal structures of some coumarin derivatives (Yang et al., 2006; 2007; 2008) have been decribed. As part of our study of the crystal structures of coumarin derivatives with 7-hydroxy, we report here the crystal structure of 8-Benzoyl-7-hydroxy-4-methyl-2H-1-benzopyran-2-one, (I).

In the molecule(I), the asymmetric unit of (I) contains one coumarin molecule and one hydration water molecules, and which are linked together by one O—H···O hydrogen bond (Table 1 and Fig. 1). The coumarin moiety and phenyl ring (two r.m.s deviations 0.0060 Å) are perpendicular to each other with a dihedral angle of 86.59 (5)° between the plane of the atoms O1—O3/C1—C9 and the plane of C12—C17.

In crystal structure of (I), translationally related molecules are linked together by O3—H3···O5ⁱ [symmetry code: (i)x, 1 + y, z] hydrogen bond, forming C(10) chains parallel to the b axis; inversionally related molecular chains are linked together by O—H···O hydrogen bond O5—H5B···O4ⁱⁱ [symmetry codes: (ii)1/2 - x, 1/2 - y, 1 - z], generating doubled chain of R₅⁶(28)[R₄⁴(20)R₄⁴(16)] ring parallel to the b axis (Table.1 and Fig. 2). Neighboring doubled chains are linked into three-dimensional crystal structure by π–π interaction Cg1···Cg1ⁱⁱⁱ [Where Cg1 is the centroid of O1/C1—C4/C9, Cg1···Cg1ⁱⁱⁱ = 3.6898 (12) Å, symmetry code: (iii) -x, y,1/2 - z].

Experimental

The mixture containing 2.8 g (10 mmol) of dry, powdered 7-benzoxy-4-methylcoumarin and 4.53 g (34 mmol) of anhydrous aluminium chloride was heated at 463 K for 2 h 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 30 min, the crude product was filtered off, washed with water. Colorless crystals of (I) suitable for X-ray structure analysis were obtained by recrystallizing from 95% water-ethanol solution [m.p. 492 K].