PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2008 November 1; 64(Pt 11): o2088.
Published online 2008 October 9. doi:  10.1107/S1600536808032005
PMCID: PMC2959561

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

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 [triangle]); Tanitame et al. (2004 [triangle]); Shao et al. (1997 [triangle]); Rendenbach-Müller et al. (1994 [triangle]); Pochet et al. (1996 [triangle]); Yang et al. (2007 [triangle], 2006 [triangle]). For a related structure, see: Yang et al. (2007 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o2088-scheme1.jpg

Experimental

Crystal data

  • C16H12O5S
  • M r = 316.32
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-64-o2088-efi6.jpg
  • 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 [triangle]) 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
  • Δρmax = 0.21 e Å−3
  • Δρmin = −0.27 e Å−3

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808032005/xu2456sup1.cif

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

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.

Refinement

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) = 1.2Ueq(C) (aromatic) and Uiso(H) = 1.5Ueq(C) (methyl).

Figures

Fig. 1.
The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level.
Fig. 2.
The crystal structure of the title compound, showing the formation of a hydrogen-bonded R33(18) ribbon along [010]. For clarity, H atoms not involving in H-bonding have been omitted. Dashed lines indicate hydrogen bonds [Symmetry codes: (*) 1/2 - x, 1/2 ...

Crystal data

C16H12O5SDx = 1.445 Mg m3
Mr = 316.32Melting point: 493 K
Orthorhombic, PbcnMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2abCell parameters from 1900 reflections
a = 23.319 (3) Åθ = 2.4–22.8°
b = 9.0865 (12) ŵ = 0.24 mm1
c = 13.7280 (17) ÅT = 298 K
V = 2908.8 (6) Å3Block, colourless
Z = 80.48 × 0.35 × 0.23 mm
F(000) = 1312

Data collection

Siemens SMART CCD area-detector diffractometer2557 independent reflections
Radiation source: fine-focus sealed tube1340 reflections with I > 2σ(I)
graphiteRint = 0.077
[var phi] and ω scansθmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −27→25
Tmin = 0.892, Tmax = 0.946k = −6→10
11238 measured reflectionsl = −16→15

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.164H-atom parameters constrained
S = 1.09w = 1/[σ2(Fo2) + (0.0635P)2 + 1.4P] where P = (Fo2 + 2Fc2)/3
2557 reflections(Δ/σ)max < 0.001
200 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = −0.27 e Å3

Special details

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)

xyzUiso*/Ueq
O10.06623 (10)0.5712 (3)0.1179 (2)0.0475 (7)
O20.01987 (13)0.7814 (3)0.1253 (2)0.0753 (10)
O30.17597 (10)0.1409 (3)0.1092 (2)0.0554 (8)
O40.25437 (12)0.0001 (4)0.0562 (3)0.0813 (11)
O50.15694 (13)−0.0921 (3)0.0244 (2)0.0686 (9)
S10.19688 (4)0.02586 (12)0.02911 (9)0.0554 (4)
C10.01573 (17)0.6497 (5)0.1241 (3)0.0511 (11)
C2−0.03663 (17)0.5658 (5)0.1266 (3)0.0518 (11)
H2−0.07120.61680.12970.062*
C3−0.03837 (15)0.4190 (4)0.1249 (3)0.0443 (10)
C40.01530 (14)0.3395 (4)0.1195 (3)0.0402 (9)
C50.06587 (16)0.4202 (4)0.1156 (3)0.0397 (9)
C60.11874 (15)0.3532 (4)0.1088 (3)0.0430 (10)
H60.15210.40880.10470.052*
C70.12071 (15)0.2032 (4)0.1081 (3)0.0431 (10)
C80.07195 (17)0.1177 (4)0.1123 (3)0.0529 (11)
H80.07430.01550.11160.063*
C90.01984 (17)0.1871 (4)0.1176 (3)0.0514 (11)
H9−0.01340.13060.11990.062*
C10−0.09430 (15)0.3386 (5)0.1251 (3)0.0669 (13)
H10A−0.12510.40790.13170.100*
H10B−0.09510.27080.17870.100*
H10C−0.09850.28550.06510.100*
C110.19416 (16)0.1231 (4)−0.0797 (3)0.0444 (10)
C120.24038 (18)0.2080 (5)−0.1072 (4)0.0699 (14)
H120.27210.2163−0.06650.084*
C130.2393 (3)0.2794 (6)−0.1940 (5)0.0937 (18)
H130.27050.3363−0.21310.112*
C140.1923 (3)0.2683 (6)−0.2538 (4)0.0906 (18)
H140.19190.3175−0.31320.109*
C150.1467 (2)0.1859 (6)−0.2267 (4)0.0723 (14)
H150.11490.1795−0.26750.087*
C160.14680 (18)0.1116 (5)−0.1394 (3)0.0583 (12)
H160.11550.0547−0.12090.070*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0504 (16)0.0403 (16)0.0519 (19)−0.0075 (12)−0.0003 (14)−0.0038 (13)
O20.089 (2)0.0449 (19)0.093 (3)0.0008 (16)−0.0127 (19)−0.0033 (18)
O30.0567 (16)0.0623 (18)0.0473 (19)0.0100 (14)−0.0067 (14)−0.0124 (15)
O40.0632 (18)0.099 (3)0.082 (2)0.0411 (17)−0.0239 (17)−0.0130 (19)
O50.084 (2)0.0457 (17)0.076 (2)−0.0071 (15)0.0033 (18)−0.0047 (16)
S10.0583 (7)0.0514 (6)0.0566 (8)0.0129 (5)−0.0072 (6)−0.0057 (6)
C10.063 (3)0.050 (3)0.041 (3)−0.003 (2)−0.005 (2)−0.003 (2)
C20.050 (2)0.067 (3)0.039 (3)0.007 (2)−0.003 (2)−0.007 (2)
C30.045 (2)0.056 (3)0.032 (2)−0.0075 (19)0.0005 (18)−0.008 (2)
C40.045 (2)0.045 (2)0.030 (2)−0.0130 (18)0.0001 (18)−0.0077 (18)
C50.050 (2)0.037 (2)0.031 (2)−0.0074 (18)−0.0024 (19)−0.0035 (17)
C60.045 (2)0.045 (2)0.039 (2)−0.0116 (18)0.0002 (18)−0.0040 (19)
C70.050 (2)0.045 (2)0.034 (2)0.0005 (19)0.0018 (19)−0.0047 (19)
C80.065 (3)0.037 (2)0.057 (3)−0.007 (2)0.003 (2)−0.003 (2)
C90.053 (3)0.044 (2)0.057 (3)−0.018 (2)0.003 (2)−0.006 (2)
C100.047 (2)0.083 (3)0.071 (4)−0.016 (2)0.003 (2)−0.011 (3)
C110.043 (2)0.043 (2)0.047 (3)0.0069 (19)−0.001 (2)−0.009 (2)
C120.061 (3)0.083 (3)0.066 (4)−0.014 (3)0.003 (3)−0.018 (3)
C130.113 (5)0.099 (4)0.069 (4)−0.029 (4)0.031 (4)−0.004 (4)
C140.146 (6)0.071 (4)0.055 (4)0.016 (4)0.016 (4)0.002 (3)
C150.090 (4)0.073 (3)0.055 (4)0.022 (3)−0.015 (3)−0.007 (3)
C160.054 (3)0.058 (3)0.063 (3)0.003 (2)−0.004 (2)−0.005 (2)

Geometric parameters (Å, °)

O1—C51.373 (4)C7—C81.378 (5)
O1—C11.379 (4)C8—C91.371 (5)
O2—C11.201 (4)C8—H80.9300
O3—C71.407 (4)C9—H90.9300
O3—S11.594 (3)C10—H10A0.9600
O4—S11.411 (3)C10—H10B0.9600
O5—S11.421 (3)C10—H10C0.9600
S1—C111.736 (4)C11—C121.378 (5)
C1—C21.440 (5)C11—C161.379 (5)
C2—C31.334 (5)C12—C131.358 (7)
C2—H20.9300C12—H120.9300
C3—C41.447 (5)C13—C141.372 (7)
C3—C101.495 (5)C13—H130.9300
C4—C91.389 (5)C14—C151.354 (7)
C4—C51.390 (4)C14—H140.9300
C5—C61.378 (5)C15—C161.376 (6)
C6—C71.364 (5)C15—H150.9300
C6—H60.9300C16—H160.9300
C5—O1—C1120.9 (3)C9—C8—H8120.8
C7—O3—S1122.4 (2)C7—C8—H8120.8
O4—S1—O5120.6 (2)C8—C9—C4121.8 (3)
O4—S1—O3102.59 (17)C8—C9—H9119.1
O5—S1—O3109.02 (17)C4—C9—H9119.1
O4—S1—C11110.2 (2)C3—C10—H10A109.5
O5—S1—C11108.70 (19)C3—C10—H10B109.5
O3—S1—C11104.37 (16)H10A—C10—H10B109.5
O2—C1—O1116.6 (4)C3—C10—H10C109.5
O2—C1—C2126.5 (4)H10A—C10—H10C109.5
O1—C1—C2116.9 (3)H10B—C10—H10C109.5
C3—C2—C1123.7 (4)C12—C11—C16120.4 (4)
C3—C2—H2118.2C12—C11—S1119.5 (3)
C1—C2—H2118.2C16—C11—S1120.1 (3)
C2—C3—C4118.3 (3)C13—C12—C11119.5 (5)
C2—C3—C10121.0 (4)C13—C12—H12120.2
C4—C3—C10120.7 (4)C11—C12—H12120.2
C9—C4—C5117.4 (3)C12—C13—C14120.4 (5)
C9—C4—C3124.4 (3)C12—C13—H13119.8
C5—C4—C3118.2 (3)C14—C13—H13119.8
O1—C5—C6115.9 (3)C15—C14—C13120.3 (5)
O1—C5—C4122.1 (3)C15—C14—H14119.9
C6—C5—C4121.9 (3)C13—C14—H14119.9
C7—C6—C5118.2 (3)C14—C15—C16120.5 (5)
C7—C6—H6120.9C14—C15—H15119.7
C5—C6—H6120.9C16—C15—H15119.7
C6—C7—C8122.4 (3)C15—C16—C11118.9 (4)
C6—C7—O3115.6 (3)C15—C16—H16120.6
C8—C7—O3121.9 (3)C11—C16—H16120.6
C9—C8—C7118.3 (4)
C7—O3—S1—O4177.3 (3)C5—C6—C7—O3−174.9 (3)
C7—O3—S1—O5−53.7 (3)S1—O3—C7—C6−125.2 (3)
C7—O3—S1—C1162.3 (3)S1—O3—C7—C858.8 (5)
C5—O1—C1—O2−179.7 (4)C6—C7—C8—C9−0.1 (6)
C5—O1—C1—C2−0.8 (5)O3—C7—C8—C9175.6 (4)
O2—C1—C2—C3179.8 (4)C7—C8—C9—C4−0.6 (6)
O1—C1—C2—C31.1 (6)C5—C4—C9—C80.2 (6)
C1—C2—C3—C4−0.4 (6)C3—C4—C9—C8179.9 (4)
C1—C2—C3—C10−178.4 (4)O4—S1—C11—C12−23.7 (4)
C2—C3—C4—C9179.7 (4)O5—S1—C11—C12−157.9 (3)
C10—C3—C4—C9−2.2 (6)O3—S1—C11—C1285.8 (3)
C2—C3—C4—C5−0.6 (5)O4—S1—C11—C16154.3 (3)
C10—C3—C4—C5177.5 (4)O5—S1—C11—C1620.0 (4)
C1—O1—C5—C6179.6 (3)O3—S1—C11—C16−96.2 (3)
C1—O1—C5—C4−0.1 (5)C16—C11—C12—C13−0.6 (6)
C9—C4—C5—O1−179.5 (3)S1—C11—C12—C13177.4 (4)
C3—C4—C5—O10.8 (5)C11—C12—C13—C140.5 (8)
C9—C4—C5—C60.8 (6)C12—C13—C14—C150.0 (8)
C3—C4—C5—C6−178.9 (3)C13—C14—C15—C16−0.4 (8)
O1—C5—C6—C7178.8 (3)C14—C15—C16—C110.3 (7)
C4—C5—C6—C7−1.5 (6)C12—C11—C16—C150.2 (6)
C5—C6—C7—C81.1 (6)S1—C11—C16—C15−177.8 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C6—H6···O4i0.932.433.325 (4)163
C8—H8···O2ii0.932.483.293 (5)145

Symmetry codes: (i) −x+1/2, y+1/2, z; (ii) x, y−1, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2456).

References

  • 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. [PubMed]
  • Rendenbach-Müller, B., Schelcker, R., Traut, M. & Weifenbach, H. (1994). Bioorg. Med. Chem. Lett.4, 1195–1198.
  • Shao, X., Ekstrand, D. H. L., Bhikhabhai, R., Kallander, C. F. R. & Gronowitz, J. S. (1997). Antivir. Chem. Chemother.8, 149–159.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Siemens (1996). SMART and SAINT Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
  • 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. [PubMed]
  • Xie, L., Takeuchi, Y., Cosentino, L. M., McPhail, A. T. & Lee, K. H. (2001). J. Med. Chem.44, 664–671. [PubMed]
  • Yang, S.-P., Han, L.-J. & Wang, D.-Q. (2007). Acta Cryst. E63, o135–o137.
  • Yang, S.-P., Han, L.-J., Wang, D.-Q. & Xia, H.-T. (2006). Acta Cryst. E62, o4350–o4352.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography