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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

5-Chloro-2-(4-methyl­phen­yl)-3-methyl­sulfinyl-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 20 June 2013; accepted 3 July 2013; online 6 July 2013)

In the title compound, C16H13ClO2S, the dihedral angle between the mean plane [r.m.s. deviation = 0.004 (2) Å] of the benzo­furan ring system and the 4-methyl­phenyl ring is 29.25 (8)°. In the crystal, inversion dimers linked by pairs of weak C—H⋯O interactions generate R22(14) loops.

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 the crystal structures of related compounds, see: Choi et al. (2007[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2007). Acta Cryst. E63, o1291-o1292.], 2009[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2009). Acta Cryst. E65, o2649.]).

[Scheme 1]

Experimental

Crystal data
  • C16H13ClO2S

  • Mr = 304.77

  • Triclinic, [P \overline 1]

  • a = 8.0694 (8) Å

  • b = 8.0763 (8) Å

  • c = 11.4208 (11) Å

  • α = 90.185 (6)°

  • β = 96.280 (6)°

  • γ = 111.701 (6)°

  • V = 686.63 (12) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.43 mm−1

  • T = 173 K

  • 0.35 × 0.34 × 0.10 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 = 0.865, Tmax = 0.958

  • 12808 measured reflections

  • 3423 independent reflections

  • 3021 reflections with I > 2σ(I)

  • Rint = 0.048

Refinement
  • R[F2 > 2σ(F2)] = 0.038

  • wR(F2) = 0.103

  • S = 1.05

  • 3423 reflections

  • 183 parameters

  • H-atom parameters constrained

  • Δρmax = 0.32 e Å−3

  • Δρmin = −0.28 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C14—H14⋯O2i 0.95 2.54 3.436 (2) 158
Symmetry code: (i) -x+1, -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 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) 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

Many compounds having a benzofuran moiety have drawn much attention due 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 continuing study of 5-chloro-3-methylsulfinyl-1-benzofuran derivatives containing phenyl (Choi et al., 2007) and 4-fluorophenyl (Choi et al., 2009) substituents in 2-position, 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 (2) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle between the mean plane of the benzofuran ring system and the 4-methylphenyl ring is 29.25 (8)°. In the crystal structure, molecules are connected by weak C—H···O hydrogen bonds (Table 1), resulting in a three-dimensional network.

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 the crystal structures of related compounds, see: Choi et al. (2007, 2009).

Experimental top

3-Chloroperoxybenzoic acid (77%, 269 mg, 1.2 mmol) was added in small portions to a stirred solution of 5-chloro-2-(4-methylphenyl)-3-methylsulfanyl-1-benzofuran (317 mg, 1.1 mmol) in dichloromethane (40 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 70%, m.p. 459–460 K; Rf = 0.49 (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 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 0.98Å for methyl H atoms. Uiso(H) = 1.2Ueq(C) for aryl and 1.5Ueq(C) for methyl H atoms. The positions of methyl hydrogens were optimized rotationally.

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 for Windows (Farrugia, 2012) 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. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as small spheres of arbitrary radius.
5-Chloro-2-(4-methylphenyl)-3-methylsulfinyl-1-benzofuran top
Crystal data top
C16H13ClO2SZ = 2
Mr = 304.77F(000) = 316
Triclinic, P1Dx = 1.474 Mg m3
Hall symbol: -P 1Melting point = 459–460 K
a = 8.0694 (8) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.0763 (8) ÅCell parameters from 4424 reflections
c = 11.4208 (11) Åθ = 2.7–28.1°
α = 90.185 (6)°µ = 0.43 mm1
β = 96.280 (6)°T = 173 K
γ = 111.701 (6)°Block, colourless
V = 686.63 (12) Å30.35 × 0.34 × 0.10 mm
Data collection top
Bruker SMART APEXII CCD
diffractometer
3423 independent reflections
Radiation source: rotating anode3021 reflections with I > 2σ(I)
Graphite multilayer monochromatorRint = 0.048
Detector resolution: 10.0 pixels mm-1θmax = 28.4°, θmin = 1.8°
ϕ and ω scansh = 1010
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
k = 1010
Tmin = 0.865, Tmax = 0.958l = 1515
12808 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)] = 0.038Hydrogen site location: difference Fourier map
wR(F2) = 0.103H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0432P)2 + 0.3137P]
where P = (Fo2 + 2Fc2)/3
3423 reflections(Δ/σ)max < 0.001
183 parametersΔρmax = 0.32 e Å3
0 restraintsΔρmin = 0.28 e Å3
Crystal data top
C16H13ClO2Sγ = 111.701 (6)°
Mr = 304.77V = 686.63 (12) Å3
Triclinic, P1Z = 2
a = 8.0694 (8) ÅMo Kα radiation
b = 8.0763 (8) ŵ = 0.43 mm1
c = 11.4208 (11) ÅT = 173 K
α = 90.185 (6)°0.35 × 0.34 × 0.10 mm
β = 96.280 (6)°
Data collection top
Bruker SMART APEXII CCD
diffractometer
3423 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
3021 reflections with I > 2σ(I)
Tmin = 0.865, Tmax = 0.958Rint = 0.048
12808 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0380 restraints
wR(F2) = 0.103H-atom parameters constrained
S = 1.05Δρmax = 0.32 e Å3
3423 reflectionsΔρmin = 0.28 e Å3
183 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
Cl10.21613 (6)0.06293 (6)0.00434 (4)0.03430 (13)
S10.79728 (5)0.32171 (5)0.40498 (4)0.02612 (12)
O10.30621 (15)0.15287 (15)0.50057 (10)0.0257 (2)
O20.82257 (18)0.19866 (17)0.31756 (13)0.0401 (3)
C10.5655 (2)0.2423 (2)0.41897 (14)0.0239 (3)
C20.4219 (2)0.1456 (2)0.32835 (14)0.0236 (3)
C30.4092 (2)0.0990 (2)0.20888 (14)0.0259 (3)
H30.51220.13280.16790.031*
C40.2396 (2)0.0014 (2)0.15325 (14)0.0269 (3)
C50.0852 (2)0.0505 (2)0.21040 (15)0.0291 (3)
H50.02840.11790.16800.035*
C60.0970 (2)0.0040 (2)0.32891 (15)0.0282 (3)
H60.00610.03700.36980.034*
C70.2666 (2)0.0929 (2)0.38407 (14)0.0241 (3)
C80.4897 (2)0.2427 (2)0.52001 (14)0.0238 (3)
C90.5607 (2)0.3179 (2)0.63960 (14)0.0238 (3)
C100.7141 (2)0.4725 (2)0.66158 (15)0.0280 (3)
H100.77380.53140.59760.034*
C110.7804 (2)0.5414 (2)0.77602 (15)0.0296 (4)
H110.88620.64580.78980.036*
C120.6930 (2)0.4586 (2)0.87084 (15)0.0282 (3)
C130.5390 (2)0.3061 (2)0.84809 (15)0.0281 (3)
H130.47800.24890.91210.034*
C140.4720 (2)0.2353 (2)0.73466 (14)0.0256 (3)
H140.36610.13090.72130.031*
C150.7646 (3)0.5323 (3)0.99514 (16)0.0390 (4)
H15A0.66530.50051.04360.059*
H15B0.82280.66240.99520.059*
H15C0.85220.48181.02760.059*
C160.8112 (3)0.5192 (2)0.32875 (16)0.0318 (4)
H16A0.93110.57490.30360.048*
H16B0.78960.60310.38150.048*
H16C0.72060.48770.25950.048*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0365 (3)0.0364 (2)0.0259 (2)0.01030 (19)0.00156 (17)0.00172 (16)
S10.0199 (2)0.0253 (2)0.0326 (2)0.00772 (16)0.00336 (15)0.00359 (15)
O10.0207 (6)0.0284 (6)0.0265 (6)0.0073 (5)0.0031 (4)0.0001 (4)
O20.0316 (7)0.0302 (6)0.0614 (9)0.0115 (6)0.0178 (6)0.0034 (6)
C10.0214 (8)0.0241 (7)0.0262 (7)0.0090 (6)0.0017 (6)0.0007 (6)
C20.0218 (8)0.0215 (7)0.0281 (8)0.0091 (6)0.0014 (6)0.0021 (6)
C30.0257 (8)0.0260 (7)0.0269 (8)0.0107 (6)0.0035 (6)0.0021 (6)
C40.0303 (9)0.0243 (7)0.0255 (7)0.0106 (7)0.0008 (6)0.0001 (6)
C50.0252 (8)0.0272 (8)0.0315 (8)0.0076 (7)0.0026 (7)0.0006 (6)
C60.0226 (8)0.0287 (8)0.0329 (8)0.0089 (7)0.0031 (6)0.0024 (6)
C70.0238 (8)0.0237 (7)0.0256 (7)0.0098 (6)0.0021 (6)0.0015 (6)
C80.0201 (8)0.0218 (7)0.0290 (8)0.0073 (6)0.0021 (6)0.0021 (6)
C90.0241 (8)0.0240 (7)0.0258 (7)0.0117 (6)0.0034 (6)0.0014 (6)
C100.0301 (9)0.0248 (7)0.0282 (8)0.0081 (7)0.0072 (7)0.0031 (6)
C110.0297 (9)0.0234 (7)0.0329 (8)0.0065 (7)0.0046 (7)0.0028 (6)
C120.0311 (9)0.0278 (8)0.0275 (8)0.0132 (7)0.0030 (7)0.0024 (6)
C130.0298 (9)0.0296 (8)0.0270 (8)0.0123 (7)0.0075 (7)0.0048 (6)
C140.0228 (8)0.0236 (7)0.0301 (8)0.0081 (6)0.0040 (6)0.0027 (6)
C150.0417 (11)0.0422 (10)0.0295 (9)0.0116 (9)0.0035 (8)0.0084 (7)
C160.0342 (10)0.0272 (8)0.0355 (9)0.0118 (7)0.0087 (7)0.0073 (7)
Geometric parameters (Å, º) top
Cl1—C41.7462 (16)C9—C101.393 (2)
S1—O21.4879 (13)C9—C141.399 (2)
S1—C11.7648 (17)C10—C111.388 (2)
S1—C161.7925 (17)C10—H100.9500
O1—C71.3768 (18)C11—C121.393 (2)
O1—C81.3790 (19)C11—H110.9500
C1—C81.364 (2)C12—C131.387 (2)
C1—C21.445 (2)C12—C151.505 (2)
C2—C71.393 (2)C13—C141.382 (2)
C2—C31.397 (2)C13—H130.9500
C3—C41.381 (2)C14—H140.9500
C3—H30.9500C15—H15A0.9800
C4—C51.396 (2)C15—H15B0.9800
C5—C61.387 (2)C15—H15C0.9800
C5—H50.9500C16—H16A0.9800
C6—C71.378 (2)C16—H16B0.9800
C6—H60.9500C16—H16C0.9800
C8—C91.459 (2)
O2—S1—C1106.64 (7)C10—C9—C8121.45 (14)
O2—S1—C16106.07 (8)C14—C9—C8119.67 (15)
C1—S1—C1697.73 (8)C11—C10—C9120.65 (15)
C7—O1—C8106.62 (12)C11—C10—H10119.7
C8—C1—C2107.24 (14)C9—C10—H10119.7
C8—C1—S1126.49 (13)C10—C11—C12120.54 (16)
C2—C1—S1125.89 (12)C10—C11—H11119.7
C7—C2—C3119.27 (15)C12—C11—H11119.7
C7—C2—C1105.00 (14)C13—C12—C11118.46 (15)
C3—C2—C1135.73 (15)C13—C12—C15120.74 (16)
C4—C3—C2116.75 (15)C11—C12—C15120.80 (16)
C4—C3—H3121.6C14—C13—C12121.65 (16)
C2—C3—H3121.6C14—C13—H13119.2
C3—C4—C5123.29 (15)C12—C13—H13119.2
C3—C4—Cl1118.71 (13)C13—C14—C9119.81 (15)
C5—C4—Cl1118.00 (13)C13—C14—H14120.1
C6—C5—C4120.20 (15)C9—C14—H14120.1
C6—C5—H5119.9C12—C15—H15A109.5
C4—C5—H5119.9C12—C15—H15B109.5
C7—C6—C5116.26 (15)H15A—C15—H15B109.5
C7—C6—H6121.9C12—C15—H15C109.5
C5—C6—H6121.9H15A—C15—H15C109.5
O1—C7—C6125.14 (14)H15B—C15—H15C109.5
O1—C7—C2110.63 (14)S1—C16—H16A109.5
C6—C7—C2124.23 (15)S1—C16—H16B109.5
C1—C8—O1110.51 (14)H16A—C16—H16B109.5
C1—C8—C9133.98 (15)S1—C16—H16C109.5
O1—C8—C9115.51 (13)H16A—C16—H16C109.5
C10—C9—C14118.87 (15)H16B—C16—H16C109.5
O2—S1—C1—C8142.96 (15)C1—C2—C7—C6179.96 (15)
C16—S1—C1—C8107.64 (15)C2—C1—C8—O10.17 (17)
O2—S1—C1—C229.09 (16)S1—C1—C8—O1173.43 (11)
C16—S1—C1—C280.31 (15)C2—C1—C8—C9179.34 (16)
C8—C1—C2—C70.40 (17)S1—C1—C8—C97.4 (3)
S1—C1—C2—C7172.92 (12)C7—O1—C8—C10.68 (17)
C8—C1—C2—C3179.75 (17)C7—O1—C8—C9179.99 (12)
S1—C1—C2—C36.9 (3)C1—C8—C9—C1029.6 (3)
C7—C2—C3—C40.1 (2)O1—C8—C9—C10149.54 (15)
C1—C2—C3—C4179.69 (16)C1—C8—C9—C14151.36 (18)
C2—C3—C4—C50.1 (2)O1—C8—C9—C1429.5 (2)
C2—C3—C4—Cl1179.18 (11)C14—C9—C10—C111.5 (2)
C3—C4—C5—C60.2 (3)C8—C9—C10—C11179.49 (15)
Cl1—C4—C5—C6179.45 (12)C9—C10—C11—C121.0 (3)
C4—C5—C6—C70.4 (2)C10—C11—C12—C130.2 (2)
C8—O1—C7—C6179.86 (15)C10—C11—C12—C15179.82 (16)
C8—O1—C7—C20.94 (16)C11—C12—C13—C140.3 (2)
C5—C6—C7—O1179.43 (14)C15—C12—C13—C14179.38 (16)
C5—C6—C7—C20.3 (2)C12—C13—C14—C90.2 (2)
C3—C2—C7—O1179.29 (13)C10—C9—C14—C131.0 (2)
C1—C2—C7—O10.83 (17)C8—C9—C14—C13179.91 (14)
C3—C2—C7—C60.1 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C14—H14···O2i0.952.543.436 (2)158
Symmetry code: (i) x+1, y, z+1.

Experimental details

Crystal data
Chemical formulaC16H13ClO2S
Mr304.77
Crystal system, space groupTriclinic, P1
Temperature (K)173
a, b, c (Å)8.0694 (8), 8.0763 (8), 11.4208 (11)
α, β, γ (°)90.185 (6), 96.280 (6), 111.701 (6)
V3)686.63 (12)
Z2
Radiation typeMo Kα
µ (mm1)0.43
Crystal size (mm)0.35 × 0.34 × 0.10
Data collection
DiffractometerBruker SMART APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.865, 0.958
No. of measured, independent and
observed [I > 2σ(I)] reflections
12808, 3423, 3021
Rint0.048
(sin θ/λ)max1)0.668
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.103, 1.05
No. of reflections3423
No. of parameters183
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.32, 0.28

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 1998).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C14—H14···O2i0.952.543.436 (2)157.5
Symmetry code: (i) x+1, y, z+1.
 

Acknowledgements

This work was supported by the Blue-Bio Industry Regional Innovation Center (RIC08-06-07) at Dongeui University as an RIC program under the Ministry of Knowledge Economy and Busan city.

References

First citationAkgul, Y. Y. & Anil, H. (2003). Phytochemistry, 63, 939–943.  Web of Science CrossRef PubMed CAS
First citationAslam, S. N., Stevenson, P. C., Kokubun, T. & Hall, D. R. (2009). Microbiol. Res. 164, 191–195.  Web of Science CrossRef PubMed CAS
First citationBrandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany.
First citationBruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationChoi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2007). Acta Cryst. E63, o1291–o1292.  Web of Science CSD CrossRef CAS IUCr Journals
First citationChoi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2009). Acta Cryst. E65, o2649.  Web of Science CSD CrossRef IUCr Journals
First citationFarrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.  Web of Science CrossRef CAS IUCr Journals
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
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
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
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

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