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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 4| April 2012| Page o1191
doi:10.1107/S1600536812012238

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

Jian-Xin Yang,a* Hong-Yan Liub and Xiang-Hui Wangc

aInstitute of Materials and Chemical Engineering, Hainan University, Haikou 570228, People's Republic of China, bSchool of Chemistry and Chemical Engineering, South China University of Technology, GuangZhou 510640, People's Republic of China, and cInstitute of Environmental Science and Engineering, Kunming University of Science and Technology, Kunming 650093, People's Republic of China
*Correspondence e-mail: yangjxmail@sohu.com

(Received 6 February 2012; accepted 21 March 2012; online 28 March 2012)

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[Xie, L., Takeuchi, Y., Cosentino, L. M., McPhail, A. T. & Lee, K. H. (2001). J. Med. Chem. 44, 664-671.]); Tanitame et al. (2004[Tanitame, A., Oyamada, Y., Ofuji, K., Kyoya, Y., Suzuki, K., Ito, H., Kawasaki, M., Nagai, K., Wachi, M. & Yamagishi, J. (2004). J. Med. Chem. 47, 3693-3696.]); Shao et al. (1997[Shao, X., Ekstrand, D. H. L., Bhikhabhai, R., Kallander, C. F. R. & Gronowitz, J. S. (1997). Antivir. Chem. Chemother. 8, 149-159.]); Rendenbach-Müller et al. (1994[Rendenbach-Müller, B., Schelcker, R., Traut, M. & Weifenbach, H. (1994). Bioorg. Med. Chem. Lett. 4, 1195-1198.]); Pochet et al. (1996[Pochet, L., Doucet, C., Schynts, M., Thierry, N., Boggeto, N., Pirotte, B., Jiang, K. Y., Masereel, B., Tulio, P. D., Delarge, J. & Reboud-Ravaux, M. (1996). J. Med. Chem. 39, 2579-2585.]). For a related structure, see: Yang et al. (2007[Yang, S.-P., Han, L.-J. & Wang, D.-Q. (2007). Acta Cryst. E63, o135-o137.]).

[Scheme 1]

Experimental

Crystal data

  • C17H14O5S

  • Mr = 330.34

  • Triclinic, [P \overline 1]

  • 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[Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.885, Tmax = 0.913

  • 8968 measured reflections

  • 4451 independent reflections

  • 3289 reflections with I > 2σ(I)

  • Rint = 0.037
Refinement

  • R[F2 > 2σ(F2)] = 0.042

  • wR(F2) = 0.099

  • S = 1.00

  • 4451 reflections

  • 211 parameters

  • H-atom parameters constrained

  • Δρmax = 0.30 e Å−3

  • Δρmin = −0.47 e Å−3

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⋯O2iv 0.95 2.58 3.506 (2) 165
C15—H15⋯O5v 0.95 2.41 3.284 (2) 152
Symmetry codes: (i) -x, -y+2, -z+1; (ii) x-1, y+1, z; (iii) x-1, y, z; (iv) x, y-1, z; (v) -x, -y+2, -z.

Data collection: CrystalClear (Rigaku, 2008[Rigaku (2008). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and DIAMOND (Brandenburg, 1999[Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXTL and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812012238/fy2046sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812012238/fy2046Isup3.cml

checkCIF report


Comment top

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).

Related literature top

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 top

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.

Refinement top

H atoms were placed in calculated positions with C—H = 0.93 Å (aromatic) and 0.96 Å (methyl), and refined in riding mode with Uiso(H) = 1.2 Ueq(C) (aromatic) and Uiso(H) = 1.5 Ueq(C) (methyl).

Structure description top

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).

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).

Computing details top

Data collection: CrystalClear (Rigaku, 2008); cell refinement: CrystalClear (Rigaku, 2008); data reduction: CrystalClear (Rigaku, 2008); 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 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are presented as a small spheres of arbitrary radius.
[Figure 2] Fig. 2. A view of the C—H···O interactions (dotted lines) in the crystal structure of the title compound.
4-Methyl-2-oxo-2H-chromen-7-yl 4-methylbenzenesulfonate top
Crystal data top
C17H14O5SZ = 2
Mr = 330.34F(000) = 344
Triclinic, P1Dx = 1.410 Mg m−3
a = 7.5582 (19) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.024 (2) ÅCell parameters from 2667 reflections
c = 13.336 (4) Åθ = 2.6–30.0°
α = 88.648 (8)°µ = 0.23 mm−1
β = 87.420 (7)°T = 153 K
γ = 74.341 (4)°Chip, colorless
V = 777.9 (3) Å30.54 × 0.41 × 0.40 mm
Data collection top
Rigaku AFC10/Saturn724+
diffractometer		4451 independent reflections
Radiation source: Rotating Anode3289 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.037
Detector resolution: 28.5714 pixels mm-1θmax = 30.0°, θmin = 2.8°
φ and ω scansh = −10→10
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		k = −11→10
Tmin = 0.885, Tmax = 0.913l = −18→17
8968 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042H-atom parameters constrained
wR(F2) = 0.099 w = 1/[σ2(Fo2) + (0.0315P)2 + 0.119P]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
4451 reflectionsΔρmax = 0.30 e Å−3
211 parametersΔρmin = −0.47 e Å−3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0116 (17)
Crystal data top
C17H14O5Sγ = 74.341 (4)°
Mr = 330.34V = 777.9 (3) Å3
Triclinic, P1Z = 2
a = 7.5582 (19) ÅMo Kα radiation
b = 8.024 (2) ŵ = 0.23 mm−1
c = 13.336 (4) ÅT = 153 K
α = 88.648 (8)°0.54 × 0.41 × 0.40 mm
β = 87.420 (7)°
Data collection top
Rigaku AFC10/Saturn724+
diffractometer		4451 independent reflections
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		3289 reflections with I > 2σ(I)
Tmin = 0.885, Tmax = 0.913Rint = 0.037
8968 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0420 restraints
wR(F2) = 0.099H-atom parameters constrained
S = 1.00Δρmax = 0.30 e Å−3
4451 reflectionsΔρmin = −0.47 e Å−3
211 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S1−0.05701 (5)0.90186 (5)0.20148 (3)0.02605 (11)
O10.63814 (14)0.58774 (12)0.35269 (7)0.0263 (2)
O20.11089 (15)0.98205 (12)0.22320 (7)0.0270 (2)
O30.88672 (15)0.39807 (14)0.40502 (9)0.0362 (3)
O4−0.14270 (15)0.87024 (14)0.29442 (7)0.0324 (3)
O5−0.15830 (17)1.02006 (14)0.13018 (8)0.0384 (3)
C10.7537 (2)0.51511 (19)0.42877 (12)0.0276 (3)
C20.7040 (2)0.58301 (19)0.52862 (12)0.0276 (3)
H20.78140.53390.58190.033*
C30.5524 (2)0.71307 (18)0.54922 (11)0.0240 (3)
C40.43676 (19)0.79009 (17)0.46707 (10)0.0211 (3)
C50.2782 (2)0.92868 (17)0.47851 (11)0.0227 (3)
H50.24480.97950.54260.027*
C60.1701 (2)0.99233 (17)0.39833 (10)0.0237 (3)
H60.06381.08720.40640.028*
C70.2198 (2)0.91503 (17)0.30561 (10)0.0222 (3)
C80.3765 (2)0.78118 (18)0.28978 (10)0.0242 (3)
H80.40940.73190.22530.029*
C90.48388 (19)0.72125 (17)0.37112 (11)0.0218 (3)
C100.0542 (2)0.70422 (18)0.14554 (10)0.0237 (3)
C110.0484 (2)0.55129 (19)0.19411 (12)0.0301 (3)
H11−0.01920.55280.25600.036*
C120.1434 (2)0.3959 (2)0.15060 (13)0.0363 (4)
H120.13840.29020.18280.044*
C130.2454 (2)0.3912 (2)0.06117 (13)0.0367 (4)
C140.2448 (2)0.5469 (2)0.01312 (12)0.0373 (4)
H140.31110.5456−0.04920.045*
C150.1497 (2)0.7033 (2)0.05420 (11)0.0310 (3)
H150.14970.80890.02040.037*
C160.4986 (2)0.7756 (2)0.65416 (11)0.0307 (3)
H16A0.58940.70930.70040.037*
H16B0.37730.75990.67310.037*
H16C0.49380.89870.65750.037*
C170.3556 (3)0.2207 (2)0.01848 (17)0.0579 (6)
H17A0.47120.18060.05330.069*
H17B0.38240.2354−0.05330.069*
H17C0.28490.13510.02760.069*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0268 (2)0.02155 (18)0.0275 (2)−0.00202 (14)−0.00334 (15)−0.00134 (14)
O10.0219 (5)0.0191 (5)0.0340 (6)0.0000 (4)0.0056 (4)−0.0021 (4)
O20.0322 (6)0.0196 (5)0.0294 (5)−0.0069 (4)−0.0047 (4)0.0032 (4)
O30.0241 (6)0.0242 (5)0.0549 (7)0.0013 (5)0.0050 (5)0.0014 (5)
O40.0301 (6)0.0361 (6)0.0309 (6)−0.0090 (5)0.0059 (5)−0.0072 (5)
O50.0431 (7)0.0268 (6)0.0391 (6)0.0033 (5)−0.0153 (5)0.0017 (5)
C10.0197 (7)0.0198 (7)0.0428 (9)−0.0054 (6)0.0024 (6)0.0019 (6)
C20.0213 (7)0.0235 (7)0.0384 (8)−0.0064 (6)−0.0035 (6)0.0024 (6)
C30.0211 (7)0.0207 (7)0.0320 (8)−0.0086 (6)−0.0010 (6)−0.0003 (6)
C40.0191 (7)0.0160 (6)0.0287 (7)−0.0058 (5)0.0022 (6)−0.0026 (5)
C50.0215 (7)0.0186 (6)0.0278 (7)−0.0053 (5)0.0036 (6)−0.0053 (5)
C60.0212 (7)0.0170 (6)0.0320 (8)−0.0036 (5)0.0025 (6)−0.0042 (6)
C70.0248 (7)0.0168 (6)0.0259 (7)−0.0070 (6)−0.0007 (6)0.0010 (5)
C80.0272 (8)0.0197 (7)0.0252 (7)−0.0062 (6)0.0044 (6)−0.0035 (5)
C90.0181 (7)0.0150 (6)0.0312 (7)−0.0035 (5)0.0055 (6)−0.0022 (5)
C100.0254 (7)0.0210 (7)0.0240 (7)−0.0046 (6)−0.0025 (6)−0.0014 (5)
C110.0331 (9)0.0256 (8)0.0317 (8)−0.0080 (7)−0.0019 (7)0.0017 (6)
C120.0378 (10)0.0211 (7)0.0501 (10)−0.0073 (7)−0.0097 (8)0.0008 (7)
C130.0276 (8)0.0295 (8)0.0517 (10)−0.0031 (7)−0.0080 (8)−0.0139 (7)
C140.0322 (9)0.0449 (10)0.0327 (9)−0.0066 (8)0.0051 (7)−0.0129 (7)
C150.0352 (9)0.0282 (8)0.0282 (8)−0.0066 (7)0.0009 (7)0.0013 (6)
C160.0311 (9)0.0295 (8)0.0319 (8)−0.0084 (7)−0.0042 (7)−0.0027 (6)
C170.0407 (11)0.0384 (10)0.0896 (16)0.0010 (9)−0.0060 (11)−0.0315 (10)
Geometric parameters (Å, º) top
S1—O51.4215 (11)C8—C91.3824 (19)
S1—O41.4219 (11)C8—H80.9500
S1—O21.6097 (11)C10—C111.384 (2)
S1—C101.7485 (15)C10—C151.387 (2)
O1—C91.3710 (16)C11—C121.386 (2)
O1—C11.3817 (18)C11—H110.9500
O2—C71.4104 (16)C12—C131.386 (2)
O3—C11.2119 (18)C12—H120.9500
C1—C21.446 (2)C13—C141.389 (2)
C2—C31.348 (2)C13—C171.507 (2)
C2—H20.9500C14—C151.379 (2)
C3—C41.4521 (19)C14—H140.9500
C3—C161.499 (2)C15—H150.9500
C4—C91.3983 (19)C16—H16A0.9800
C4—C51.4028 (19)C16—H16B0.9800
C5—C61.3782 (19)C16—H16C0.9800
C5—H50.9500C17—H17A0.9800
C6—C71.3868 (19)C17—H17B0.9800
C6—H60.9500C17—H17C0.9800
C7—C81.379 (2)
O5—S1—O4120.25 (8)O1—C9—C4121.76 (13)
O5—S1—O2103.06 (6)C8—C9—C4122.18 (13)
O4—S1—O2109.02 (6)C11—C10—C15121.11 (14)
O5—S1—C10110.90 (7)C11—C10—S1119.45 (12)
O4—S1—C10109.26 (7)C15—C10—S1119.43 (11)
O2—S1—C10102.75 (6)C10—C11—C12118.67 (15)
C9—O1—C1121.11 (12)C10—C11—H11120.7
C7—O2—S1117.90 (8)C12—C11—H11120.7
O3—C1—O1116.22 (14)C11—C12—C13121.42 (15)
O3—C1—C2126.26 (15)C11—C12—H12119.3
O1—C1—C2117.51 (13)C13—C12—H12119.3
C3—C2—C1122.73 (14)C12—C13—C14118.46 (15)
C3—C2—H2118.6C12—C13—C17120.29 (17)
C1—C2—H2118.6C14—C13—C17121.25 (17)
C2—C3—C4118.39 (13)C15—C14—C13121.24 (16)
C2—C3—C16121.80 (14)C15—C14—H14119.4
C4—C3—C16119.79 (13)C13—C14—H14119.4
C9—C4—C5117.80 (13)C14—C15—C10119.03 (15)
C9—C4—C3118.45 (13)C14—C15—H15120.5
C5—C4—C3123.74 (13)C10—C15—H15120.5
C6—C5—C4121.12 (13)C3—C16—H16A109.5
C6—C5—H5119.4C3—C16—H16B109.5
C4—C5—H5119.4H16A—C16—H16B109.5
C5—C6—C7118.61 (13)C3—C16—H16C109.5
C5—C6—H6120.7H16A—C16—H16C109.5
C7—C6—H6120.7H16B—C16—H16C109.5
C8—C7—C6122.58 (13)C13—C17—H17A109.5
C8—C7—O2118.74 (12)C13—C17—H17B109.5
C6—C7—O2118.60 (13)H17A—C17—H17B109.5
C7—C8—C9117.65 (13)C13—C17—H17C109.5
C7—C8—H8121.2H17A—C17—H17C109.5
C9—C8—H8121.2H17B—C17—H17C109.5
O1—C9—C8116.05 (12)
O5—S1—O2—C7167.92 (10)C1—O1—C9—C40.17 (19)
O4—S1—O2—C739.08 (11)C7—C8—C9—O1179.78 (12)
C10—S1—O2—C7−76.75 (11)C7—C8—C9—C41.0 (2)
C9—O1—C1—O3−179.83 (12)C5—C4—C9—O1178.86 (12)
C9—O1—C1—C21.12 (19)C3—C4—C9—O1−2.0 (2)
O3—C1—C2—C3−179.45 (15)C5—C4—C9—C8−2.4 (2)
O1—C1—C2—C3−0.5 (2)C3—C4—C9—C8176.75 (12)
C1—C2—C3—C4−1.3 (2)O5—S1—C10—C11−135.28 (13)
C1—C2—C3—C16176.97 (13)O4—S1—C10—C11−0.47 (14)
C2—C3—C4—C92.54 (19)O2—S1—C10—C11115.18 (12)
C16—C3—C4—C9−175.78 (13)O5—S1—C10—C1545.99 (14)
C2—C3—C4—C5−178.39 (13)O4—S1—C10—C15−179.20 (12)
C16—C3—C4—C53.3 (2)O2—S1—C10—C15−63.55 (13)
C9—C4—C5—C61.5 (2)C15—C10—C11—C121.2 (2)
C3—C4—C5—C6−177.61 (13)S1—C10—C11—C12−177.49 (12)
C4—C5—C6—C70.8 (2)C10—C11—C12—C131.1 (2)
C5—C6—C7—C8−2.3 (2)C11—C12—C13—C14−2.6 (2)
C5—C6—C7—O2−178.95 (12)C11—C12—C13—C17176.63 (15)
S1—O2—C7—C892.71 (14)C12—C13—C14—C151.8 (2)
S1—O2—C7—C6−90.55 (13)C17—C13—C14—C15−177.42 (16)
C6—C7—C8—C91.5 (2)C13—C14—C15—C100.4 (2)
O2—C7—C8—C9178.07 (12)C11—C10—C15—C14−2.0 (2)
C1—O1—C9—C8−178.66 (12)S1—C10—C15—C14176.72 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5—H5···O4i0.952.503.447 (2)176
C6—H6···O3ii0.952.493.380 (2)156
C11—H11···O3iii0.952.503.355 (2)150
C12—H12···O2iv0.952.583.506 (2)165
C15—H15···O5v0.952.413.284 (2)152
Symmetry codes: (i) −x, −y+2, −z+1; (ii) x−1, y+1, z; (iii) x−1, y, z; (iv) x, y−1, z; (v) −x, −y+2, −z.

Experimental details

Crystal data
Chemical formulaC17H14O5S
Mr330.34
Crystal system, space groupTriclinic, P1
Temperature (K)153
a, b, c (Å)7.5582 (19), 8.024 (2), 13.336 (4)
α, β, γ (°)88.648 (8), 87.420 (7), 74.341 (4)
V (Å3)777.9 (3)
Z2
Radiation typeMo Kα
µ (mm−1)0.23
Crystal size (mm)0.54 × 0.41 × 0.40
Data collection
DiffractometerRigaku AFC10/Saturn724+
Absorption correctionMulti-scan
(ABSCOR; Higashi, 1995)
Tmin, Tmax0.885, 0.913
No. of measured, independent and
observed [I > 2σ(I)] reflections		8968, 4451, 3289
Rint0.037
(sin θ/λ)max (Å−1)0.704
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.099, 1.00
No. of reflections4451
No. of parameters211
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.30, −0.47

Computer programs: CrystalClear (Rigaku, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1999), SHELXTL (Sheldrick, 2008) and publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5—H5···O4i0.952.503.447 (2)176
C6—H6···O3ii0.952.493.380 (2)156
C11—H11···O3iii0.952.503.355 (2)150
C12—H12···O2iv0.952.583.506 (2)165
C15—H15···O5v0.952.413.284 (2)152
Symmetry codes: (i) −x, −y+2, −z+1; (ii) x−1, y+1, z; (iii) x−1, y, z; (iv) x, y−1, z; (v) −x, −y+2, −z.
 

Acknowledgements

The authors are grateful to the National Natural Science Foundation of China (No. 20962007) and the Creative Talents Plan of Hainan University 211 project.

References

First citationBrandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
 First citationHigashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.  Google Scholar
 First citationPochet, L., Doucet, C., Schynts, M., Thierry, N., Boggeto, N., Pirotte, B., Jiang, K. Y., Masereel, B., Tulio, P. D., Delarge, J. & Reboud-Ravaux, M. (1996). J. Med. Chem. 39, 2579–2585.  CrossRef CAS PubMed Web of Science Google Scholar
 First citationRendenbach-Müller, B., Schelcker, R., Traut, M. & Weifenbach, H. (1994). Bioorg. Med. Chem. Lett. 4, 1195–1198.  CrossRef Web of Science Google Scholar
 First citationRigaku (2008). CrystalClear. Rigaku Corporation, Tokyo, Japan.  Google Scholar
 First citationShao, X., Ekstrand, D. H. L., Bhikhabhai, R., Kallander, C. F. R. & Gronowitz, J. S. (1997). Antivir. Chem. Chemother. 8, 149–159.  CAS Google Scholar
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 First citationTanitame, A., Oyamada, Y., Ofuji, K., Kyoya, Y., Suzuki, K., Ito, H., Kawasaki, M., Nagai, K., Wachi, M. & Yamagishi, J. (2004). J. Med. Chem. 47, 3693–3696.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationXie, L., Takeuchi, Y., Cosentino, L. M., McPhail, A. T. & Lee, K. H. (2001). J. Med. Chem. 44, 664–671.  Web of Science CSD CrossRef PubMed CAS Google Scholar
 First citationYang, S.-P., Han, L.-J. & Wang, D.-Q. (2007). Acta Cryst. E63, o135–o137.  Web of Science CSD CrossRef IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

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ISSN: 2056-9890
Volume 68| Part 4| April 2012| Page o1191
doi:10.1107/S1600536812012238
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