4-Methyl-2-oxo-2,3-dihydro-1-benzopyran-7-yl benzene­sulfonate

Shu-Ping Yang; Da-Qi Wang; Li-Jun Han; Yu-Fen Liu

doi:10.1107/S1600536808032005

. 2008 Oct 9;64(Pt 11):o2088. doi: 10.1107/S1600536808032005

4-Methyl-2-oxo-2,3-dihydro-1-benzopyran-7-yl benzenesulfonate

Shu-Ping Yang ^a,^*, Da-Qi Wang ^b, Li-Jun Han ^c, Yu-Fen Liu ^a

PMCID: PMC2959561 PMID: 21580953

Abstract

The title compound, C₁₆H₁₂O₅S, is a derivative of coumarin. The dihedral angle between the coumarin ring system and the phenyl ring is 65.9 (1)°. In the crystal structure, molecules are linked by weak C—H⋯O hydrogen bonding to form molecular ribbons.

Related literature

For general background, see: Xie et al. (2001 ▶); Tanitame et al. (2004 ▶); Shao et al. (1997 ▶); Rendenbach-Müller et al. (1994 ▶); Pochet et al. (1996 ▶); Yang et al. (2007 ▶, 2006 ▶). For a related structure, see: Yang et al. (2007 ▶).

Experimental

Crystal data

C₁₆H₁₂O₅S
M _r = 316.32
Orthorhombic,
a = 23.319 (3) Å
b = 9.0865 (12) Å
c = 13.7280 (17) Å
V = 2908.8 (6) Å³
Z = 8
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 298 (2) K
0.48 × 0.35 × 0.23 mm

Data collection

Siemens SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.892, T _max = 0.946
11238 measured reflections
2557 independent reflections
1340 reflections with I > 2σ(I)
R _int = 0.077

Refinement

R[F ² > 2σ(F ²)] = 0.049
wR(F ²) = 0.164
S = 1.09
2557 reflections
200 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.27 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/S1600536808032005/xu2456sup1.cif

e-64-o2088-sup1.cif^{(18.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808032005/xu2456Isup2.hkl

e-64-o2088-Isup2.hkl^{(125.7KB, 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
C6—H6⋯O4ⁱ	0.93	2.43	3.325 (4)	163
C8—H8⋯O2ⁱⁱ	0.93	2.48	3.293 (5)	145

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

Acknowledgments

The authors acknowledge the financial support of the Technology Science Foundation of Huaihai Institute of Technology, China.

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. We have recently reported the crystal structures of some coumarin derivatives (Yang et al., 2007, 2006). As part of our study of the crystal structures of coumarin derivatives, we report here the crystal structure of the title coumarin derivative.

The molecular structure is shown in Fig. 1. The dihedral angle between the coumarin ring system and the phenyl ring is 65.9 (1)°. The terminal S═O bond distances of 1.411 (3) and 1.421 (3) 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 to form the ribbon structure (Table 1 and Fig. 2).

Experimental

To an anhydrous pyridine solution (10 ml) of 7-hydroxy-4-methyl-coumarin (1.76 g, 10 mmol), a solution of phenylsulfonyl chloride (11 mmol) was slowly added at 278–283 K with stirring for 30 min. The reaction mixture was stirred continuously for 12 h at room temperature and then poured into ice–water (200 ml). The solid obtained was filtered off, washed with 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 one week.