4-Methyl-2-oxo-2H-chromen-7-yl 4-methyl­benzene­sulfonate

Jian-Xin Yang; Hong-Yan Liu; Xiang-Hui Wang

doi:10.1107/S1600536812012238

. 2012 Mar 28;68(Pt 4):o1191. doi: 10.1107/S1600536812012238

4-Methyl-2-oxo-2H-chromen-7-yl 4-methylbenzenesulfonate

Jian-Xin Yang ^a,^*, Hong-Yan Liu ^b, Xiang-Hui Wang ^c

PMCID: PMC3344128 PMID: 22606131

Abstract

In the title compound, C₁₇H₁₄O₅S, the coumarin ring system is nearly planar, with a maximum deviation of 0.034 (2) Å from the mean plane. The dihedral angle between the benzene ring and the coumarin ring system is 56.11 (6)°. The crystal packing is stabilized by C—H⋯O hydrogen bonding, which forms a three-dimensional framework.

Related literature

For the biological 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: Yang et al. (2007 ▶).

Experimental

Crystal data

C₁₇H₁₄O₅S
M _r = 330.34
Triclinic,
a = 7.5582 (19) Å
b = 8.024 (2) Å
c = 13.336 (4) Å
α = 88.648 (8)°
β = 87.420 (7)°
γ = 74.341 (4)°
V = 777.9 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 153 K
0.54 × 0.41 × 0.40 mm

Data collection

Rigaku AFC10/Saturn724+ diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T _min = 0.885, T _max = 0.913
8968 measured reflections
4451 independent reflections
3289 reflections with I > 2σ(I)
R _int = 0.037

Refinement

R[F ² > 2σ(F ²)] = 0.042
wR(F ²) = 0.099
S = 1.00
4451 reflections
211 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.47 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 DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: SHELXTL and publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812012238/fy2046sup1.cif

e-68-o1191-sup1.cif^{(19KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812012238/fy2046Isup2.hkl

e-68-o1191-Isup2.hkl^{(218KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812012238/fy2046Isup3.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
C5—H5⋯O4ⁱ	0.95	2.50	3.447 (2)	176
C6—H6⋯O3ⁱⁱ	0.95	2.49	3.380 (2)	156
C11—H11⋯O3ⁱⁱⁱ	0.95	2.50	3.355 (2)	150
C12—H12⋯O2^iv	0.95	2.58	3.506 (2)	165
C15—H15⋯O5^v	0.95	2.41	3.284 (2)	152

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

Acknowledgments

The authors are grateful to the National Natural Science Foundation of China (No. 20962007) and the Creative Talents Plan of 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. The dihedral angle between the coumarin ring system and the phenyl ring is 56.11 (6)°. The terminal S═O bond distances of 1.4215 (11) and 1.4219 (11) Å agree with 1.4207 (19) and 1.4331 (19) Å found in a related compound, 4-methyl-7-phenylsulfonamido-2H-1-benzopyran-2-one (Yang et al., 2007).

In the crystal the molecules are linked by weak C—H···O hydrogen bonding (Table 1 and Fig. 2).

Experimental

To a mixture of para-toluenesulfonic acid (0.5 g) and acetylacetic ester (10.50 mmol), 4-hydroxyphenyl-4-methylbenzenesulfonate (10.50 mmol) was slowly added at 278–288 K with stirring for 30 min. The reaction mixture was stirred continuously for 12 h at room temperature and then poured into ice–water (100 ml). The solid obtained 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 evaporation of an ethanol solution over a period of two days.