Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Previous article
Next article
Previous article
Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Next article

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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 3| March 2010| Page o706
doi:10.1107/S1600536810006823

5-Chloro-2-(4-chloro­phen­yl)-7-methyl-3-methyl­sulfinyl-1-benzo­furan

Hong Dae Choi,a Pil Ja Seo,a Byeng Wha Sonb and Uk Leeb*

aDepartment of Chemistry, Dongeui University, San 24 Kaya-dong Busanjin-gu, Busan 614-714, Republic of Korea, and bDepartment of Chemistry, Pukyong National University, 599-1 Daeyeon 3-dong, Nam-gu, Busan 608-737, Republic of Korea
*Correspondence e-mail: uklee@pknu.ac.kr

(Received 22 February 2010; accepted 23 February 2010; online 27 February 2010)

In the title compound, C16H12Cl2O2S, the O atom and the methyl group of the methyl­sulfinyl substituent lie on opposite sides of the plane through the benzofuran fragment. The 4-chloro­phenyl ring is rotated out of the benzofuran plane, as indicated by the dihedral angle of 15.91 (4)°. In the crystal, mol­ecules are linked into chains along the b axis by weak inter­molecular C—H⋯O hydrogen bonds.

Related literature

For the crystal structures of similar 2-(4-fluoro­phen­yl)-5-halo-3-methyl­sulfinyl-1-benzofuran derivatives, see: Choi et al. (2009[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2009). Acta Cryst. E65, o2649.], 2010a[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010a). Acta Cryst. E66, o44.],b[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010b). Acta Cryst. E66, o104.]). For the biological activity of benzofuran compounds, see: Aslam et al. (2006[Aslam, S. N., Stevenson, P. C., Phythian, S. J., Veitch, N. C. & Hall, D. R. (2006). Tetrahedron, 62, 4214-4226.]); Galal et al. (2009[Galal, S. A., Abd El-All, A. S., Abdallah, M. M. & El-Diwani, H. I. (2009). Bioorg. Med. Chem. Lett. 19, 2420-2428.]); Khan et al. (2005[Khan, M. W., Alam, M. J., Rashid, M. A. & Chowdhury, R. (2005). Bioorg. Med. Chem. 13, 4796-4805.]). For natural products with benzofuran rings, see: Akgul & Anil (2003[Akgul, Y. Y. & Anil, H. (2003). Phytochemistry, 63, 939-943.]); Soekamto et al. (2003[Soekamto, N. H., Achmad, S. A., Ghisalberti, E. L., Hakim, E. H. & Syah, Y. M. (2003). Phytochemistry, 64, 831-834.]).

[Scheme 1]

Experimental

Crystal data

  • C16H12Cl2O2S

  • Mr = 339.22

  • Triclinic, [P \overline 1]

  • a = 7.538 (2) Å

  • b = 9.734 (2) Å

  • c = 11.277 (3) Å

  • α = 72.525 (2)°

  • β = 88.846 (3)°

  • γ = 70.058 (2)°

  • V = 738.8 (3) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.58 mm−1

  • T = 173 K

  • 0.50 × 0.50 × 0.45 mm
Data collection

  • Bruker SMART APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.760, Tmax = 0.780

  • 6331 measured reflections

  • 3170 independent reflections

  • 2879 reflections with I > 2σ(I)

  • Rint = 0.017
Refinement

  • R[F2 > 2σ(F2)] = 0.031

  • wR(F2) = 0.089

  • S = 1.03

  • 3170 reflections

  • 192 parameters

  • H-atom parameters constrained

  • Δρmax = 0.67 e Å−3

  • Δρmin = −0.33 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C15—H15A⋯O2i 0.96 2.52 3.216 (2) 130
Symmetry code: (i) x, y-1, z.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and DIAMOND (Brandenburg, 1998[Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810006823/hg2648sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810006823/hg2648Isup2.hkl

checkCIF report


Comment top

Compounds containing benzofuran skeleton display significant biological activities such as antifungal (Aslam et al., 2006), antitumor and antiviral (Galal et al., 2009), antimicrobial (Khan et al., 2005) properties. These compounds are widely occurring in nature (Akgul & Anil, 2003; Soekamto et al., 2003). As a part of our ongoing studies of the effect of side chain substituents on the solid state structures of 2-(4-fluorophenyl)-5-halo-3-methylsulfinyl-1-benzofuran analogues (Choi et al., 2009, 2010a,b), we report the crystal structure of the title compound (Fig. 1).

The benzofuran unit is essentially planar, with a mean deviation of 0.013 (1) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle formed by the plane of the benzofuran and the 4-chlorophenyl ring is 15.91 (4)°. The crystal packing (Fig. 2) is stabilized by a weak intermolecular C—H···O hydrogen bond between the methyl H atom and the oxygen of the S═O unit, with a C15—H15A···O2i (Table 1).

Related literature top

For the crystal structures of similar 2-(4-fluorophenyl)-5-halo-3-methylsulfinyl-1-benzofuran derivatives, see: Choi et al. (2009, 2010a,b). For the biological activity of benzofuran compounds, see: Aslam et al. (2006); Galal et al. (2009); Khan et al. (2005). For natural products with benzofuran rings, see: Akgul & Anil (2003); Soekamto et al. (2003).

Experimental top

77% 3-Chloroperoxybenzoic acid (247 mg, 1.1 mmol) was added in small portions to a stirred solution of 5-chloro-2-(4-chlorophenyl)-7-methyl-3-methylsulfanyl-1-benzofuran (323 mg, 1.0 mmol) in dichloromethane (30 mL) at 273 K. After being stirred at room temperature for 4h, the mixture was washed with saturated sodium bicarbonate solution and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated at reduced pressure. The residue was purified by column chromatography (hexane–ethyl acetate, 1:1 v/v) to afford the title compound as a colorless solid [yield 79%, m.p. 456–457 K; Rf = 0.62 (hexane–ethyl acetate, 1:1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in tetrahydrofuran at room temperature.

Refinement top

All H atoms were positioned geometrically and refined using a riding model, with C—H = 0.93 Å for aryl and 0.96 Å for methyl H atoms. Uiso(H) = 1.2Ueq(C) for aryl and 1.5Ueq(C) for methyl H atoms.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 50 % probability level. H atoms are presented as a small spheres of arbitrary radius.
[Figure 2] Fig. 2. C—H···O interactions (dotted lines) in the crystal structure of the title compound. [Symmetry codes: i) x, y - 1, z; ii) x, y + 1, z.]
5-Chloro-2-(4-chlorophenyl)-7-methyl-3-methylsulfinyl-1-benzofuran top
Crystal data top
C16H12Cl2O2SZ = 2
Mr = 339.22F(000) = 348
Triclinic, P1Dx = 1.525 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.538 (2) ÅCell parameters from 5112 reflections
b = 9.734 (2) Åθ = 2.3–27.5°
c = 11.277 (3) ŵ = 0.58 mm−1
α = 72.525 (2)°T = 173 K
β = 88.846 (3)°Block, colourless
γ = 70.058 (2)°0.50 × 0.50 × 0.45 mm
V = 738.8 (3) Å3
Data collection top
Bruker SMART APEXII CCD
diffractometer		3170 independent reflections
Radiation source: Rotating Anode2879 reflections with I > 2σ(I)
Bruker HELIOS graded multilayer optics monochromatorRint = 0.017
Detector resolution: 10.0 pixels mm-1θmax = 27.0°, θmin = 2.3°
ϕ and ω scansh = −9→9
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		k = −12→12
Tmin = 0.760, Tmax = 0.780l = −14→14
6331 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.031Hydrogen site location: difference Fourier map
wR(F2) = 0.089H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0425P)2 + 0.4419P]
where P = (Fo2 + 2Fc2)/3
3170 reflections(Δ/σ)max < 0.001
192 parametersΔρmax = 0.67 e Å−3
0 restraintsΔρmin = −0.33 e Å−3
Crystal data top
C16H12Cl2O2Sγ = 70.058 (2)°
Mr = 339.22V = 738.8 (3) Å3
Triclinic, P1Z = 2
a = 7.538 (2) ÅMo Kα radiation
b = 9.734 (2) ŵ = 0.58 mm−1
c = 11.277 (3) ÅT = 173 K
α = 72.525 (2)°0.50 × 0.50 × 0.45 mm
β = 88.846 (3)°
Data collection top
Bruker SMART APEXII CCD
diffractometer		3170 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		2879 reflections with I > 2σ(I)
Tmin = 0.760, Tmax = 0.780Rint = 0.017
6331 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0310 restraints
wR(F2) = 0.089H-atom parameters constrained
S = 1.03Δρmax = 0.67 e Å−3
3170 reflectionsΔρmin = −0.33 e Å−3
192 parameters
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
Cl10.54735 (6)0.25715 (5)1.03989 (4)0.03540 (12)
Cl2−0.06257 (7)0.78823 (6)−0.05751 (4)0.04700 (14)
S0.19164 (6)0.77859 (5)0.56104 (4)0.03206 (12)
O20.3263 (2)0.78670 (16)0.65093 (15)0.0479 (4)
O10.31330 (15)0.36506 (12)0.52197 (10)0.0257 (2)
C10.2500 (2)0.58258 (17)0.57346 (15)0.0256 (3)
C20.3368 (2)0.45451 (18)0.68431 (15)0.0251 (3)
C30.3874 (2)0.43701 (19)0.80827 (15)0.0276 (3)
H30.36280.52100.83730.033*
C40.4757 (2)0.28803 (19)0.88482 (15)0.0276 (3)
C50.5149 (2)0.15889 (18)0.84399 (15)0.0277 (3)
H50.57610.06130.89980.033*
C60.4640 (2)0.17381 (18)0.72181 (15)0.0259 (3)
C70.3749 (2)0.32444 (18)0.64609 (14)0.0240 (3)
C80.2391 (2)0.52362 (17)0.47881 (15)0.0251 (3)
C90.1655 (2)0.58997 (18)0.34785 (15)0.0260 (3)
C100.0411 (2)0.7420 (2)0.29918 (16)0.0320 (4)
H100.00390.80250.35160.038*
C11−0.0275 (2)0.8040 (2)0.17491 (16)0.0336 (4)
H11−0.10790.90600.14320.040*
C120.0253 (2)0.7123 (2)0.09853 (16)0.0321 (4)
C130.1472 (2)0.5606 (2)0.14326 (17)0.0340 (4)
H130.18080.50030.09050.041*
C140.2181 (2)0.50046 (19)0.26736 (16)0.0295 (3)
H140.30160.39940.29780.035*
C150.4973 (3)0.03952 (19)0.67375 (17)0.0342 (4)
H15A0.38060.02170.66800.051*
H15B0.5895−0.05050.72990.051*
H15C0.54300.06160.59260.051*
C16−0.0290 (3)0.8027 (2)0.63063 (19)0.0402 (4)
H16A−0.00920.72430.70990.060*
H16B−0.11930.79450.57670.060*
H16C−0.07640.90210.64240.060*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0418 (2)0.0380 (2)0.0257 (2)−0.01599 (18)−0.00416 (16)−0.00618 (17)
Cl20.0449 (3)0.0568 (3)0.0281 (2)−0.0095 (2)−0.00846 (19)−0.0063 (2)
S0.0416 (2)0.0211 (2)0.0340 (2)−0.01348 (17)0.00087 (18)−0.00631 (16)
O20.0564 (9)0.0358 (7)0.0589 (9)−0.0222 (6)−0.0092 (7)−0.0175 (7)
O10.0296 (6)0.0221 (5)0.0243 (5)−0.0094 (4)−0.0009 (4)−0.0053 (4)
C10.0278 (7)0.0208 (7)0.0280 (8)−0.0102 (6)0.0006 (6)−0.0052 (6)
C20.0253 (7)0.0227 (7)0.0289 (8)−0.0111 (6)0.0017 (6)−0.0070 (6)
C30.0320 (8)0.0257 (8)0.0276 (8)−0.0131 (6)−0.0001 (6)−0.0082 (6)
C40.0273 (8)0.0315 (8)0.0248 (8)−0.0137 (6)0.0000 (6)−0.0059 (6)
C50.0257 (7)0.0241 (8)0.0296 (8)−0.0088 (6)0.0000 (6)−0.0028 (6)
C60.0244 (7)0.0225 (7)0.0303 (8)−0.0095 (6)0.0019 (6)−0.0061 (6)
C70.0241 (7)0.0250 (7)0.0245 (7)−0.0112 (6)0.0009 (6)−0.0069 (6)
C80.0240 (7)0.0215 (7)0.0289 (8)−0.0091 (6)0.0012 (6)−0.0052 (6)
C90.0247 (7)0.0277 (8)0.0262 (8)−0.0125 (6)0.0020 (6)−0.0057 (6)
C100.0319 (8)0.0309 (8)0.0301 (8)−0.0074 (7)0.0007 (7)−0.0094 (7)
C110.0298 (8)0.0307 (8)0.0325 (9)−0.0066 (7)−0.0017 (7)−0.0031 (7)
C120.0272 (8)0.0420 (10)0.0241 (8)−0.0136 (7)−0.0016 (6)−0.0041 (7)
C130.0346 (9)0.0372 (9)0.0308 (9)−0.0114 (7)0.0008 (7)−0.0128 (7)
C140.0299 (8)0.0272 (8)0.0303 (8)−0.0101 (6)−0.0003 (6)−0.0071 (7)
C150.0419 (9)0.0230 (8)0.0351 (9)−0.0088 (7)0.0016 (7)−0.0082 (7)
C160.0454 (10)0.0299 (9)0.0426 (10)−0.0085 (8)0.0067 (8)−0.0131 (8)
Geometric parameters (Å, º) top
Cl1—C41.7468 (17)C8—C91.457 (2)
Cl2—C121.7358 (17)C9—C101.399 (2)
S—O21.4862 (14)C9—C141.402 (2)
S—C11.7672 (16)C10—C111.380 (2)
S—C161.797 (2)C10—H100.9300
O1—C71.3782 (19)C11—C121.380 (3)
O1—C81.3794 (18)C11—H110.9300
C1—C81.371 (2)C12—C131.387 (3)
C1—C21.444 (2)C13—C141.383 (2)
C2—C71.395 (2)C13—H130.9300
C2—C31.401 (2)C14—H140.9300
C3—C41.380 (2)C15—H15A0.9600
C3—H30.9300C15—H15B0.9600
C4—C51.403 (2)C15—H15C0.9600
C5—C61.389 (2)C16—H16A0.9600
C5—H50.9300C16—H16B0.9600
C6—C71.389 (2)C16—H16C0.9600
C6—C151.504 (2)
O2—S—C1107.20 (8)C10—C9—C8121.71 (15)
O2—S—C16106.67 (10)C14—C9—C8119.94 (14)
C1—S—C1697.03 (8)C11—C10—C9121.30 (16)
C7—O1—C8106.66 (12)C11—C10—H10119.3
C8—C1—C2107.57 (14)C9—C10—H10119.3
C8—C1—S126.90 (12)C10—C11—C12118.87 (16)
C2—C1—S125.25 (12)C10—C11—H11120.6
C7—C2—C3119.54 (14)C12—C11—H11120.6
C7—C2—C1104.68 (14)C11—C12—C13121.64 (16)
C3—C2—C1135.77 (14)C11—C12—Cl2119.29 (14)
C4—C3—C2116.18 (14)C13—C12—Cl2119.07 (14)
C4—C3—H3121.9C14—C13—C12119.06 (16)
C2—C3—H3121.9C14—C13—H13120.5
C3—C4—C5123.34 (15)C12—C13—H13120.5
C3—C4—Cl1118.85 (13)C13—C14—C9120.76 (16)
C5—C4—Cl1117.80 (12)C13—C14—H14119.6
C6—C5—C4121.32 (15)C9—C14—H14119.6
C6—C5—H5119.3C6—C15—H15A109.5
C4—C5—H5119.3C6—C15—H15B109.5
C7—C6—C5114.60 (14)H15A—C15—H15B109.5
C7—C6—C15121.71 (15)C6—C15—H15C109.5
C5—C6—C15123.68 (14)H15A—C15—H15C109.5
O1—C7—C6124.10 (14)H15B—C15—H15C109.5
O1—C7—C2110.89 (13)S—C16—H16A109.5
C6—C7—C2125.01 (15)S—C16—H16B109.5
C1—C8—O1110.18 (14)H16A—C16—H16B109.5
C1—C8—C9134.67 (15)S—C16—H16C109.5
O1—C8—C9115.15 (13)H16A—C16—H16C109.5
C10—C9—C14118.35 (15)H16B—C16—H16C109.5
O2—S—C1—C8−144.91 (15)C1—C2—C7—O1−1.46 (17)
C16—S—C1—C8105.17 (16)C3—C2—C7—C6−1.0 (2)
O2—S—C1—C228.29 (16)C1—C2—C7—C6178.09 (15)
C16—S—C1—C2−81.64 (15)C2—C1—C8—O10.14 (17)
C8—C1—C2—C70.79 (17)S—C1—C8—O1174.32 (11)
S—C1—C2—C7−173.51 (12)C2—C1—C8—C9178.83 (16)
C8—C1—C2—C3179.69 (17)S—C1—C8—C9−7.0 (3)
S—C1—C2—C35.4 (3)C7—O1—C8—C1−1.03 (16)
C7—C2—C3—C40.8 (2)C7—O1—C8—C9180.00 (12)
C1—C2—C3—C4−177.97 (17)C1—C8—C9—C10−16.6 (3)
C2—C3—C4—C50.0 (2)O1—C8—C9—C10162.01 (14)
C2—C3—C4—Cl1178.74 (12)C1—C8—C9—C14163.90 (17)
C3—C4—C5—C6−0.7 (2)O1—C8—C9—C14−17.5 (2)
Cl1—C4—C5—C6−179.45 (12)C14—C9—C10—C11−0.7 (2)
C4—C5—C6—C70.5 (2)C8—C9—C10—C11179.83 (15)
C4—C5—C6—C15−178.23 (15)C9—C10—C11—C121.4 (3)
C8—O1—C7—C6−177.99 (14)C10—C11—C12—C13−1.0 (3)
C8—O1—C7—C21.57 (16)C10—C11—C12—Cl2179.16 (13)
C5—C6—C7—O1179.82 (13)C11—C12—C13—C14−0.3 (3)
C15—C6—C7—O1−1.4 (2)Cl2—C12—C13—C14179.60 (13)
C5—C6—C7—C20.3 (2)C12—C13—C14—C91.1 (3)
C15—C6—C7—C2179.10 (15)C10—C9—C14—C13−0.6 (2)
C3—C2—C7—O1179.43 (13)C8—C9—C14—C13178.90 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C15—H15A···O2i0.962.523.216 (2)130
Symmetry code: (i) x, y−1, z.

Experimental details

Crystal data
Chemical formulaC16H12Cl2O2S
Mr339.22
Crystal system, space groupTriclinic, P1
Temperature (K)173
a, b, c (Å)7.538 (2), 9.734 (2), 11.277 (3)
α, β, γ (°)72.525 (2), 88.846 (3), 70.058 (2)
V (Å3)738.8 (3)
Z2
Radiation typeMo Kα
µ (mm−1)0.58
Crystal size (mm)0.50 × 0.50 × 0.45
Data collection
DiffractometerBruker SMART APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.760, 0.780
No. of measured, independent and
observed [I > 2σ(I)] reflections		6331, 3170, 2879
Rint0.017
(sin θ/λ)max (Å−1)0.639
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.031, 0.089, 1.03
No. of reflections3170
No. of parameters192
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.67, −0.33

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C15—H15A···O2i0.962.523.216 (2)129.5
Symmetry code: (i) x, y−1, z.
 

References

First citationAkgul, Y. Y. & Anil, H. (2003). Phytochemistry, 63, 939–943.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationAslam, S. N., Stevenson, P. C., Phythian, S. J., Veitch, N. C. & Hall, D. R. (2006). Tetrahedron, 62, 4214–4226.  Web of Science CrossRef CAS Google Scholar
 First citationBrandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
 First citationBruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationChoi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2009). Acta Cryst. E65, o2649.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationChoi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010a). Acta Cryst. E66, o44.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationChoi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010b). Acta Cryst. E66, o104.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
 First citationGalal, S. A., Abd El-All, A. S., Abdallah, M. M. & El-Diwani, H. I. (2009). Bioorg. Med. Chem. Lett. 19, 2420–2428.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationKhan, M. W., Alam, M. J., Rashid, M. A. & Chowdhury, R. (2005). Bioorg. Med. Chem. 13, 4796–4805.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSoekamto, N. H., Achmad, S. A., Ghisalberti, E. L., Hakim, E. H. & Syah, Y. M. (2003). Phytochemistry, 64, 831–834.  Web of Science CrossRef PubMed CAS 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.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 3| March 2010| Page o706
doi:10.1107/S1600536810006823
Follow Acta Cryst. E
Sign up for e-alerts
E-alerts
Follow Acta Cryst. on Twitter
Twitter
Follow us on facebook
Facebook
Sign up for RSS feeds
RSS