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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

3-(3-Chloro­phenyl­sulfon­yl)-2,5-di­methyl-1-benzo­furan

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 August 2011; accepted 2 September 2011; online 14 September 2011)

In the title molecule, C16H13ClO3S, the 3-chloro­phenyl ring makes a dihedral angle of 76.30 (5)° with the mean plane of the benzofuran fragment. In the crystal, pairs of inter­molecular C—H⋯π inter­actions link the mol­ecules into inversion dimers.

Related literature

For the pharmacological activity of benzofuran compounds, see: Aslam et al. (2009[Aslam, S. N., Stevenson, P. C., Kokubun, T. & Hall, D. R. (2009). Microbiol. Res. 164, 191-195.]); 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.]). For structural studies of 3-(4-chloro­phenyl­sulfon­yl)-2-methyl-1-benzofuran derivatives, see: Choi et al. (2010[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010). Acta Cryst. E66, o3065.], 2011[Choi, H. D., Seo, P. J. & Lee, U. (2011). Acta Cryst. E67, o1226.]).

[Scheme 1]

Experimental

Crystal data
  • C16H13ClO3S

  • Mr = 320.77

  • Triclinic, [P \overline 1]

  • a = 8.1000 (4) Å

  • b = 8.8622 (5) Å

  • c = 10.6898 (6) Å

  • α = 84.023 (3)°

  • β = 81.514 (3)°

  • γ = 72.378 (3)°

  • V = 721.90 (7) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.42 mm−1

  • T = 173 K

  • 0.28 × 0.27 × 0.19 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 = 0.579, Tmax = 0.746

  • 13538 measured reflections

  • 3622 independent reflections

  • 2951 reflections with I > 2σ(I)

  • Rint = 0.051

Refinement
  • R[F2 > 2σ(F2)] = 0.040

  • wR(F2) = 0.110

  • S = 1.05

  • 3622 reflections

  • 192 parameters

  • H-atom parameters constrained

  • Δρmax = 0.39 e Å−3

  • Δρmin = −0.40 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C2–C7 benzene ring.

D—H⋯A D—H H⋯A DA D—H⋯A
C9—H9CCgi 0.98 2.73 3.663 (2) 159
Symmetry code: (i) -x, -y, -z+1.

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


Comment top

Recently, many compounds containing a benzofuran ring system have drawn much attention owing to their valuable pharmacological properties such as antibacterial and antifungal, antitumor and antiviral, and antimicrobial activities (Aslam et al., 2009, Galal et al., 2009, Khan et al., 2005). These benzofuran derivatives occur in a wide range of natural products (Akgul & Anil, 2003; Soekamto et al., 2003). As a part of our ongoing study of the substituent effect on the solid state structures of 3-(4-chlorophenylsulfonyl)-2-methyl-1-benzofuran analogues (Choi et al., 2010, 2011), we report herein the crystal structure of the title compound.

In the title molecule (Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.004 (1) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle formed by the 3-chlorophenyl ring and the mean plane of the benzofuran fragment is 76.30 (5)° . The crystal packing (Fig.2) is stabilized by intermolecular C—H···π interactions between a methyl H atom and the benzene ring (Table 1; C9—H9C···Cgi, Cg is the centroid of the C2–C7 benzene ring).

Related literature top

For the pharmacological activity of benzofuran compounds, see: Aslam et al. (2009); Galal et al. (2009); Khan et al. (2005). For natural products with benzofuran rings, see: Akgul & Anil (2003); Soekamto et al. (2003). For structural studies of 3-(4-chlorophenylsulfonyl)-2-methyl-1-benzofuran derivatives, see: Choi et al. (2010, 2011).

Experimental top

77% 3-chloroperoxybenzoic acid (514 mg, 2.3 mmol) was added in small portions to a stirred solution of 3-(3-chlorophenylsulfanyl)-2,5-dimethyl-1-benzofuran (317 mg, 1.1 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, 4:1 v/v) to afford the title compound as a colorless solid [yield 68%, m.p. 396–397 K; Rf = 0.75 (hexane–ethyl acetate, 4:1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in acetone at room temperature.

Refinement top

All H atoms were positioned geometrically and refined using a riding model, with C—H = 0.95 Å for aryl and 0.99 Å for methyl H atoms. Uiso(H) = 1.2Ueq(C) for aryl and 1.5Ueq(C) for methyl H atoms.

Structure description top

Recently, many compounds containing a benzofuran ring system have drawn much attention owing to their valuable pharmacological properties such as antibacterial and antifungal, antitumor and antiviral, and antimicrobial activities (Aslam et al., 2009, Galal et al., 2009, Khan et al., 2005). These benzofuran derivatives occur in a wide range of natural products (Akgul & Anil, 2003; Soekamto et al., 2003). As a part of our ongoing study of the substituent effect on the solid state structures of 3-(4-chlorophenylsulfonyl)-2-methyl-1-benzofuran analogues (Choi et al., 2010, 2011), we report herein the crystal structure of the title compound.

In the title molecule (Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.004 (1) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle formed by the 3-chlorophenyl ring and the mean plane of the benzofuran fragment is 76.30 (5)° . The crystal packing (Fig.2) is stabilized by intermolecular C—H···π interactions between a methyl H atom and the benzene ring (Table 1; C9—H9C···Cgi, Cg is the centroid of the C2–C7 benzene ring).

For the pharmacological activity of benzofuran compounds, see: Aslam et al. (2009); Galal et al. (2009); Khan et al. (2005). For natural products with benzofuran rings, see: Akgul & Anil (2003); Soekamto et al. (2003). For structural studies of 3-(4-chlorophenylsulfonyl)-2-methyl-1-benzofuran derivatives, see: Choi et al. (2010, 2011).

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 small spheres of arbitrary radius.
[Figure 2] Fig. 2. A view of the C—H···π interactions (dotted lines) in the crystal structure of the title compound. [Symmetry codes: (i) - x, - y, - z + 1.]
3-(3-Chlorophenylsulfonyl)-2,5-dimethyl-1-benzofuran top
Crystal data top
C16H13ClO3SZ = 2
Mr = 320.77F(000) = 332
Triclinic, P1Dx = 1.476 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.1000 (4) ÅCell parameters from 5186 reflections
b = 8.8622 (5) Åθ = 2.4–27.9°
c = 10.6898 (6) ŵ = 0.42 mm1
α = 84.023 (3)°T = 173 K
β = 81.514 (3)°Block, colourless
γ = 72.378 (3)°0.28 × 0.27 × 0.19 mm
V = 721.90 (7) Å3
Data collection top
Bruker SMART APEXII CCD
diffractometer
3622 independent reflections
Radiation source: rotating anode2951 reflections with I > 2σ(I)
Graphite multilayer monochromatorRint = 0.051
Detector resolution: 10.0 pixels mm-1θmax = 28.4°, θmin = 1.9°
φ and ω scansh = 1010
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
k = 1111
Tmin = 0.579, Tmax = 0.746l = 1414
13538 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)] = 0.040Hydrogen site location: difference Fourier map
wR(F2) = 0.110H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0497P)2 + 0.243P]
where P = (Fo2 + 2Fc2)/3
3622 reflections(Δ/σ)max < 0.001
192 parametersΔρmax = 0.39 e Å3
0 restraintsΔρmin = 0.40 e Å3
Crystal data top
C16H13ClO3Sγ = 72.378 (3)°
Mr = 320.77V = 721.90 (7) Å3
Triclinic, P1Z = 2
a = 8.1000 (4) ÅMo Kα radiation
b = 8.8622 (5) ŵ = 0.42 mm1
c = 10.6898 (6) ÅT = 173 K
α = 84.023 (3)°0.28 × 0.27 × 0.19 mm
β = 81.514 (3)°
Data collection top
Bruker SMART APEXII CCD
diffractometer
3622 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
2951 reflections with I > 2σ(I)
Tmin = 0.579, Tmax = 0.746Rint = 0.051
13538 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0400 restraints
wR(F2) = 0.110H-atom parameters constrained
S = 1.05Δρmax = 0.39 e Å3
3622 reflectionsΔρmin = 0.40 e Å3
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
S10.33167 (5)0.43504 (5)0.29715 (4)0.02475 (13)
Cl10.08568 (7)0.78553 (6)0.04210 (5)0.04248 (16)
O10.49244 (16)0.00637 (14)0.20581 (12)0.0310 (3)
O20.45023 (15)0.49763 (14)0.20924 (13)0.0328 (3)
O30.31247 (17)0.46293 (15)0.42888 (12)0.0324 (3)
C10.3859 (2)0.23236 (19)0.28520 (16)0.0239 (3)
C20.3302 (2)0.12036 (19)0.37751 (16)0.0242 (3)
C30.2342 (2)0.1260 (2)0.49708 (16)0.0272 (4)
H30.18720.22330.53720.033*
C40.2087 (2)0.0133 (2)0.55658 (17)0.0298 (4)
C50.2811 (2)0.1561 (2)0.49675 (19)0.0342 (4)
H50.26260.25050.53890.041*
C60.3782 (2)0.1647 (2)0.3793 (2)0.0341 (4)
H60.42730.26210.33950.041*
C70.3998 (2)0.0244 (2)0.32300 (17)0.0274 (4)
C80.4815 (2)0.1509 (2)0.18512 (17)0.0273 (4)
C90.1031 (3)0.0119 (3)0.68477 (19)0.0404 (5)
H9A0.11400.07300.73190.061*
H9B0.14620.11430.73160.061*
H9C0.01980.00630.67440.061*
C100.5727 (2)0.1939 (2)0.06278 (18)0.0367 (4)
H10A0.53430.30930.04590.055*
H10B0.54550.14260.00520.055*
H10C0.69890.15840.06650.055*
C110.1232 (2)0.51080 (19)0.24554 (15)0.0241 (3)
C120.0193 (2)0.4771 (2)0.31850 (17)0.0287 (4)
H120.00560.41490.39630.034*
C130.1810 (2)0.5353 (2)0.27665 (18)0.0326 (4)
H130.27890.51090.32500.039*
C140.2017 (2)0.6286 (2)0.16502 (17)0.0313 (4)
H140.31330.66830.13620.038*
C150.0585 (2)0.6636 (2)0.09564 (17)0.0290 (4)
C160.1054 (2)0.6038 (2)0.13328 (16)0.0277 (4)
H160.20370.62590.08350.033*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0225 (2)0.0215 (2)0.0316 (2)0.00858 (15)0.00493 (16)0.00078 (16)
Cl10.0428 (3)0.0451 (3)0.0349 (3)0.0092 (2)0.0093 (2)0.0141 (2)
O10.0274 (6)0.0253 (6)0.0376 (7)0.0053 (5)0.0013 (5)0.0050 (5)
O20.0245 (6)0.0294 (7)0.0460 (8)0.0130 (5)0.0032 (5)0.0051 (5)
O30.0383 (7)0.0286 (6)0.0335 (7)0.0114 (5)0.0106 (5)0.0027 (5)
C10.0210 (7)0.0221 (7)0.0294 (8)0.0071 (6)0.0048 (6)0.0008 (6)
C20.0198 (7)0.0225 (8)0.0315 (9)0.0071 (6)0.0072 (6)0.0010 (6)
C30.0259 (8)0.0260 (8)0.0300 (9)0.0075 (6)0.0059 (7)0.0003 (7)
C40.0257 (8)0.0330 (9)0.0325 (9)0.0115 (7)0.0093 (7)0.0067 (7)
C50.0314 (9)0.0254 (9)0.0469 (11)0.0114 (7)0.0093 (8)0.0083 (8)
C60.0310 (9)0.0222 (8)0.0495 (12)0.0075 (7)0.0062 (8)0.0024 (8)
C70.0219 (8)0.0256 (8)0.0343 (9)0.0062 (6)0.0040 (7)0.0008 (7)
C80.0218 (8)0.0256 (8)0.0339 (9)0.0059 (6)0.0053 (7)0.0001 (7)
C90.0420 (11)0.0465 (11)0.0343 (10)0.0199 (9)0.0036 (8)0.0096 (9)
C100.0323 (9)0.0402 (10)0.0331 (10)0.0079 (8)0.0025 (8)0.0003 (8)
C110.0222 (8)0.0223 (8)0.0273 (8)0.0061 (6)0.0024 (6)0.0010 (6)
C120.0264 (8)0.0293 (9)0.0288 (9)0.0083 (7)0.0019 (7)0.0047 (7)
C130.0237 (8)0.0375 (10)0.0349 (10)0.0095 (7)0.0001 (7)0.0023 (8)
C140.0241 (8)0.0338 (9)0.0330 (9)0.0034 (7)0.0054 (7)0.0011 (7)
C150.0307 (9)0.0263 (8)0.0270 (9)0.0046 (7)0.0045 (7)0.0016 (7)
C160.0264 (8)0.0257 (8)0.0298 (9)0.0079 (7)0.0008 (7)0.0012 (7)
Geometric parameters (Å, º) top
S1—O31.4328 (13)C6—H60.9500
S1—O21.4355 (12)C8—C101.478 (2)
S1—C11.7289 (17)C9—H9A0.9800
S1—C111.7659 (17)C9—H9B0.9800
Cl1—C151.7334 (18)C9—H9C0.9800
O1—C81.366 (2)C10—H10A0.9800
O1—C71.383 (2)C10—H10B0.9800
C1—C81.357 (2)C10—H10C0.9800
C1—C21.449 (2)C11—C161.383 (2)
C2—C71.387 (2)C11—C121.387 (2)
C2—C31.392 (2)C12—C131.377 (3)
C3—C41.386 (2)C12—H120.9500
C3—H30.9500C13—C141.380 (3)
C4—C51.401 (3)C13—H130.9500
C4—C91.504 (3)C14—C151.381 (2)
C5—C61.376 (3)C14—H140.9500
C5—H50.9500C15—C161.376 (2)
C6—C71.373 (3)C16—H160.9500
O3—S1—O2119.46 (8)C4—C9—H9A109.5
O3—S1—C1107.56 (8)C4—C9—H9B109.5
O2—S1—C1109.13 (8)H9A—C9—H9B109.5
O3—S1—C11107.49 (8)C4—C9—H9C109.5
O2—S1—C11107.47 (8)H9A—C9—H9C109.5
C1—S1—C11104.80 (8)H9B—C9—H9C109.5
C8—O1—C7106.97 (13)C8—C10—H10A109.5
C8—C1—C2107.83 (15)C8—C10—H10B109.5
C8—C1—S1126.08 (13)H10A—C10—H10B109.5
C2—C1—S1126.02 (12)C8—C10—H10C109.5
C7—C2—C3119.05 (16)H10A—C10—H10C109.5
C7—C2—C1104.37 (15)H10B—C10—H10C109.5
C3—C2—C1136.58 (16)C16—C11—C12121.36 (16)
C4—C3—C2118.71 (16)C16—C11—S1119.09 (12)
C4—C3—H3120.6C12—C11—S1119.55 (13)
C2—C3—H3120.6C13—C12—C11119.07 (16)
C3—C4—C5119.84 (16)C13—C12—H12120.5
C3—C4—C9120.42 (17)C11—C12—H12120.5
C5—C4—C9119.74 (17)C12—C13—C14120.52 (16)
C6—C5—C4122.43 (17)C12—C13—H13119.7
C6—C5—H5118.8C14—C13—H13119.7
C4—C5—H5118.8C13—C14—C15119.29 (17)
C7—C6—C5116.06 (17)C13—C14—H14120.4
C7—C6—H6122.0C15—C14—H14120.4
C5—C6—H6122.0C16—C15—C14121.53 (16)
C6—C7—O1125.54 (16)C16—C15—Cl1119.16 (14)
C6—C7—C2123.90 (16)C14—C15—Cl1119.31 (14)
O1—C7—C2110.56 (15)C15—C16—C11118.19 (16)
C1—C8—O1110.26 (15)C15—C16—H16120.9
C1—C8—C10134.82 (17)C11—C16—H16120.9
O1—C8—C10114.92 (15)
O3—S1—C1—C8151.41 (16)C1—C2—C7—O10.08 (19)
O2—S1—C1—C820.43 (19)C2—C1—C8—O10.2 (2)
C11—S1—C1—C894.41 (17)S1—C1—C8—O1177.39 (12)
O3—S1—C1—C231.89 (17)C2—C1—C8—C10179.7 (2)
O2—S1—C1—C2162.86 (14)S1—C1—C8—C102.5 (3)
C11—S1—C1—C282.29 (16)C7—O1—C8—C10.2 (2)
C8—C1—C2—C70.06 (19)C7—O1—C8—C10179.65 (15)
S1—C1—C2—C7177.27 (13)O3—S1—C11—C16133.45 (14)
C8—C1—C2—C3179.0 (2)O2—S1—C11—C163.68 (16)
S1—C1—C2—C33.8 (3)C1—S1—C11—C16112.32 (14)
C7—C2—C3—C41.3 (3)O3—S1—C11—C1246.03 (16)
C1—C2—C3—C4179.93 (18)O2—S1—C11—C12175.80 (14)
C2—C3—C4—C50.9 (3)C1—S1—C11—C1268.19 (16)
C2—C3—C4—C9178.90 (17)C16—C11—C12—C131.3 (3)
C3—C4—C5—C60.1 (3)S1—C11—C12—C13179.25 (14)
C9—C4—C5—C6179.68 (18)C11—C12—C13—C141.4 (3)
C4—C5—C6—C70.3 (3)C12—C13—C14—C150.2 (3)
C5—C6—C7—O1179.85 (17)C13—C14—C15—C161.9 (3)
C5—C6—C7—C20.1 (3)C13—C14—C15—Cl1178.12 (15)
C8—O1—C7—C6179.81 (18)C14—C15—C16—C112.0 (3)
C8—O1—C7—C20.20 (19)Cl1—C15—C16—C11178.02 (13)
C3—C2—C7—C60.9 (3)C12—C11—C16—C150.4 (3)
C1—C2—C7—C6179.93 (17)S1—C11—C16—C15179.09 (13)
C3—C2—C7—O1179.07 (15)
Hydrogen-bond geometry (Å, º) top
Cg is the centroid of the C2–C7 benzene ring.
D—H···AD—HH···AD···AD—H···A
C9—H9C···Cgi0.982.733.663 (2)159
Symmetry code: (i) x, y, z+1.

Experimental details

Crystal data
Chemical formulaC16H13ClO3S
Mr320.77
Crystal system, space groupTriclinic, P1
Temperature (K)173
a, b, c (Å)8.1000 (4), 8.8622 (5), 10.6898 (6)
α, β, γ (°)84.023 (3), 81.514 (3), 72.378 (3)
V3)721.90 (7)
Z2
Radiation typeMo Kα
µ (mm1)0.42
Crystal size (mm)0.28 × 0.27 × 0.19
Data collection
DiffractometerBruker SMART APEXII CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.579, 0.746
No. of measured, independent and
observed [I > 2σ(I)] reflections
13538, 3622, 2951
Rint0.051
(sin θ/λ)max1)0.670
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.040, 0.110, 1.05
No. of reflections3622
No. of parameters192
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.39, 0.40

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
Cg is the centroid of the C2–C7 benzene ring.
D—H···AD—HH···AD···AD—H···A
C9—H9C···Cgi0.982.733.663 (2)159.1
Symmetry code: (i) x, y, z+1.
 

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., Kokubun, T. & Hall, D. R. (2009). Microbiol. Res. 164, 191–195.  Web of Science CrossRef PubMed 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. & Lee, U. (2011). Acta Cryst. E67, o1226.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationChoi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010). Acta Cryst. E66, o3065.  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
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds