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

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ISSN: 2056-9890

2-(4-Fluoro­phen­yl)-5-iodo-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 30 November 2009; accepted 1 December 2009; online 4 December 2009)

In the title compound, C15H10FIO2S, the O atom and the methyl group of the methyl­sulfinyl substituent are located on opposite sides of the plane through the benzofuran fragment. The 4-fluoro­phenyl ring is rotated out of the benzofuran plane by a dihedral angle of 28.33 (5)°. The crystal structure is stabilized by a weak non-classical inter­molecular C—H⋯O hydrogen bond and an I⋯O halogen interaction [3.211 (1) Å].

Related literature

For the crystal structures of similar 2-(4-fluoro­phen­yl)-3-methyl­sulfinyl-1-benzofuran derivatives, see: Choi et al. (2009a[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2009a). Acta Cryst. E65, o2608.],b[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2009b). Acta Cryst. E65, o2649.]). For natural products with benzofuran ring systems, 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 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.]). For a review of halogen bonding, see: Politzer et al. (2007[Politzer, P., Lane, P., Concha, M. C., Ma, Y. & Murray, J. S. (2007). J. Mol. Model. 13, 305-311.]).

[Scheme 1]

Experimental

Crystal data
  • C15H10FIO2S

  • Mr = 400.19

  • Triclinic, [P \overline 1]

  • a = 8.1045 (2) Å

  • b = 8.2699 (2) Å

  • c = 11.0999 (3) Å

  • α = 94.538 (1)°

  • β = 91.118 (1)°

  • γ = 111.982 (1)°

  • V = 686.73 (3) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 2.49 mm−1

  • T = 173 K

  • 0.32 × 0.31 × 0.30 mm

Data collection
  • Bruker SMART APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). SADABS. APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.504, Tmax = 0.526

  • 12180 measured reflections

  • 3179 independent reflections

  • 3130 reflections with I > 2σ(I)

  • Rint = 0.024

Refinement
  • R[F2 > 2σ(F2)] = 0.018

  • wR(F2) = 0.047

  • S = 1.17

  • 3179 reflections

  • 182 parameters

  • H-atom parameters constrained

  • Δρmax = 0.32 e Å−3

  • Δρmin = −0.90 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C10—H10⋯O2i 0.95 2.53 3.432 (2) 158
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). SADABS. APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). SADABS. APEX2 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

Molecules involving benzofuran moiety have attracted widespread interest owing to their presence in natural products (Akgul & Anil, 2003; Soekamto et al., 2003) and their biological activity (Aslam et al., 2006; Galal et al., 2009). As a part of our continuing studies of the effect of side chain substituents on the solid state structures of 2-(4-fluorophenyl)-3-methylsulfinyl-1-benzofuran analogues (Choi et al., 2009a,b), we report the crystal structure of the title compound (Fig. 1).

The benzofuran unit is essentially planar, with a mean deviation of 0.010 (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-fluorophenyl ring is 28.33 (5)°. The crystal packing (Fig. 2) is stabilized by a weak non-classical intermolecular C—H···O hydrogen bond between the 4-fluorophenyl H atom and the oxygen of the SO unit, with a C10—H10···O2i (Table 1), and an I···O halogen bond between the iodine and the oxygen of the SO unit [I···O2ii = 3.211 (1) Å; C—I···Oii = 170.98 (5)°] (Politzer et al., 2007).

Related literature top

For the crystal structures of similar 2-(4-fluorophenyl)-3-methylsulfinyl-1-benzofuran derivatives, see: Choi et al. (2009a,b). For natural products with benzofuran ring systems, see: Akgul & Anil (2003); Soekamto et al. (2003). For the biological activity of benzofuran compounds, see: Aslam et al. (2006); Galal et al. (2009). For a review of halogen bonding, see: Politzer et al. (2007).

Experimental top

77% 3-Chloroperoxybenzoic acid (247 mg, 1.1 mmol) was added in small portions to a stirred solution of 2-(4-fluorophenyl)-5-iodo-3-methylsulfanyl-1-benzofuran (384 mg, 1.0 mmol) in dichloromethane (20 mL) at 273 K. After being stirred at room temperature for 3h, the mixture was washed with saturated sodium bicarbonate solution and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated in vacuum. The residue was purified by column chromatography (hexane–ethyl acetate, 1:1 v/v) to afford the title compound as a colorless solid [yield 87%, m.p. 485–486 K; Rf = 0.66 (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 chloroforrm at room temperature.

Refinement top

All H atoms were positioned geometrically and refined using a riding model, with C—H = 0.95 Å for aromatic H atoms and 0.98 Å for methyl H atoms, and with Uiso(H) = 1.2Ueq(C) for aromatic H atoms 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 and C—I···O interactions (dotted lines) in the crystal structure of the title compound. [Symmetry codes: (i) - x + 1, - y + 1, - z + 1; (ii) - x + 1, - y + 1, - z; (iii) x, y, z + 1.]
2-(4-Fluorophenyl)-5-iodo-3-methylsulfinyl-1-benzofuran top
Crystal data top
C15H10FIO2SZ = 2
Mr = 400.19F(000) = 388
Triclinic, P1Dx = 1.935 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.1045 (2) ÅCell parameters from 9982 reflections
b = 8.2699 (2) Åθ = 2.7–27.7°
c = 11.0999 (3) ŵ = 2.49 mm1
α = 94.538 (1)°T = 173 K
β = 91.118 (1)°Block, colourless
γ = 111.982 (1)°0.32 × 0.31 × 0.30 mm
V = 686.73 (3) Å3
Data collection top
Bruker SMART APEXII CCD
diffractometer
3179 independent reflections
Radiation source: Rotating Anode3130 reflections with I > 2σ(I)
HELIOS monochromatorRint = 0.024
Detector resolution: 10.0 pixels mm-1θmax = 27.7°, θmin = 1.8°
ϕ and ω scansh = 1010
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
k = 1010
Tmin = 0.504, Tmax = 0.526l = 1314
12180 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)] = 0.018Hydrogen site location: difference Fourier map
wR(F2) = 0.047H-atom parameters constrained
S = 1.17 w = 1/[σ2(Fo2) + (0.0241P)2 + 0.2941P]
where P = (Fo2 + 2Fc2)/3
3179 reflections(Δ/σ)max < 0.001
182 parametersΔρmax = 0.32 e Å3
0 restraintsΔρmin = 0.90 e Å3
Crystal data top
C15H10FIO2Sγ = 111.982 (1)°
Mr = 400.19V = 686.73 (3) Å3
Triclinic, P1Z = 2
a = 8.1045 (2) ÅMo Kα radiation
b = 8.2699 (2) ŵ = 2.49 mm1
c = 11.0999 (3) ÅT = 173 K
α = 94.538 (1)°0.32 × 0.31 × 0.30 mm
β = 91.118 (1)°
Data collection top
Bruker SMART APEXII CCD
diffractometer
3179 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
3130 reflections with I > 2σ(I)
Tmin = 0.504, Tmax = 0.526Rint = 0.024
12180 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0180 restraints
wR(F2) = 0.047H-atom parameters constrained
S = 1.17Δρmax = 0.32 e Å3
3179 reflectionsΔρmin = 0.90 e Å3
182 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
I0.388646 (14)0.197645 (13)0.026745 (9)0.02319 (5)
S0.80967 (5)0.78626 (5)0.39558 (4)0.01979 (9)
F1.07549 (17)0.74121 (17)0.98010 (11)0.0369 (3)
O10.65247 (16)0.31158 (15)0.51009 (11)0.0203 (2)
O20.67539 (17)0.81288 (17)0.31415 (13)0.0269 (3)
C10.7317 (2)0.5608 (2)0.41682 (15)0.0185 (3)
C20.6277 (2)0.4171 (2)0.33021 (15)0.0176 (3)
C30.5720 (2)0.3991 (2)0.20821 (15)0.0195 (3)
H30.60190.49760.16240.023*
C40.4713 (2)0.2317 (2)0.15682 (15)0.0195 (3)
C50.4243 (2)0.0842 (2)0.22213 (16)0.0218 (3)
H50.35370.02800.18340.026*
C60.4802 (2)0.1007 (2)0.34311 (16)0.0217 (3)
H60.45090.00240.38890.026*
C70.5807 (2)0.2682 (2)0.39309 (15)0.0189 (3)
C80.7428 (2)0.4910 (2)0.52316 (15)0.0185 (3)
C90.8296 (2)0.5608 (2)0.64234 (16)0.0189 (3)
C100.7577 (2)0.4728 (2)0.74357 (16)0.0210 (3)
H100.65150.37080.73400.025*
C110.8411 (2)0.5344 (2)0.85731 (17)0.0240 (3)
H110.79350.47520.92620.029*
C120.9944 (2)0.6832 (2)0.86850 (17)0.0247 (4)
C131.0692 (2)0.7737 (2)0.77148 (18)0.0258 (4)
H131.17470.87630.78230.031*
C140.9860 (2)0.7105 (2)0.65755 (17)0.0230 (3)
H141.03600.76970.58910.028*
C150.9920 (3)0.7971 (3)0.3035 (2)0.0335 (4)
H15A0.94740.71590.23040.050*
H15B1.07790.76460.34910.050*
H15C1.05060.91660.28060.050*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I0.03081 (8)0.02065 (7)0.01672 (7)0.00884 (5)0.00240 (5)0.00103 (4)
S0.02125 (19)0.01521 (18)0.0224 (2)0.00624 (15)0.00127 (15)0.00201 (15)
F0.0418 (7)0.0385 (7)0.0225 (6)0.0071 (5)0.0113 (5)0.0010 (5)
O10.0245 (6)0.0177 (6)0.0171 (6)0.0059 (5)0.0003 (5)0.0025 (4)
O20.0258 (6)0.0245 (6)0.0324 (7)0.0108 (5)0.0005 (5)0.0085 (5)
C10.0200 (7)0.0166 (7)0.0185 (8)0.0067 (6)0.0011 (6)0.0009 (6)
C20.0188 (7)0.0157 (7)0.0188 (8)0.0070 (6)0.0021 (6)0.0012 (6)
C30.0235 (8)0.0182 (7)0.0175 (8)0.0086 (6)0.0009 (6)0.0026 (6)
C40.0225 (8)0.0210 (8)0.0159 (8)0.0095 (6)0.0008 (6)0.0001 (6)
C50.0238 (8)0.0190 (8)0.0210 (9)0.0067 (6)0.0021 (6)0.0005 (6)
C60.0256 (8)0.0175 (8)0.0214 (9)0.0067 (6)0.0039 (6)0.0049 (6)
C70.0212 (7)0.0208 (8)0.0154 (8)0.0087 (6)0.0022 (6)0.0023 (6)
C80.0187 (7)0.0168 (7)0.0201 (8)0.0066 (6)0.0021 (6)0.0015 (6)
C90.0200 (7)0.0210 (8)0.0177 (8)0.0102 (6)0.0014 (6)0.0017 (6)
C100.0217 (8)0.0217 (8)0.0203 (8)0.0091 (6)0.0017 (6)0.0020 (6)
C110.0280 (9)0.0263 (9)0.0196 (9)0.0118 (7)0.0022 (7)0.0045 (7)
C120.0276 (9)0.0273 (9)0.0200 (9)0.0122 (7)0.0057 (7)0.0004 (7)
C130.0220 (8)0.0261 (9)0.0257 (9)0.0058 (7)0.0025 (7)0.0006 (7)
C140.0212 (8)0.0247 (8)0.0220 (9)0.0068 (7)0.0014 (6)0.0047 (7)
C150.0265 (9)0.0312 (10)0.0470 (13)0.0128 (8)0.0145 (9)0.0157 (9)
Geometric parameters (Å, º) top
I—C42.096 (2)C6—C71.380 (2)
I—O2i3.211 (1)C6—H60.9500
S—O21.491 (1)C8—C91.455 (2)
S—C11.768 (2)C9—C141.397 (2)
S—C151.792 (2)C9—C101.403 (2)
F—C121.354 (2)C10—C111.385 (3)
O1—C71.376 (2)C10—H100.9500
O1—C81.381 (2)C11—C121.378 (3)
C1—C81.370 (2)C11—H110.9500
C1—C21.444 (2)C12—C131.379 (3)
C2—C71.394 (2)C13—C141.388 (3)
C2—C31.398 (2)C13—H130.9500
C3—C41.385 (2)C14—H140.9500
C3—H30.9500C15—H15A0.9800
C4—C51.401 (2)C15—H15B0.9800
C5—C61.388 (3)C15—H15C0.9800
C5—H50.9500
C4—I—O2i170.98 (5)C1—C8—C9135.10 (16)
O2—S—C1107.38 (8)O1—C8—C9114.45 (14)
O2—S—C15105.67 (9)C14—C9—C10119.35 (16)
C1—S—C1598.36 (9)C14—C9—C8121.35 (16)
C7—O1—C8106.78 (13)C10—C9—C8119.27 (15)
C8—C1—C2107.00 (14)C11—C10—C9120.17 (17)
C8—C1—S125.99 (13)C11—C10—H10119.9
C2—C1—S126.68 (13)C9—C10—H10119.9
C7—C2—C3119.08 (15)C12—C11—C10118.64 (17)
C7—C2—C1105.32 (14)C12—C11—H11120.7
C3—C2—C1135.60 (15)C10—C11—H11120.7
C4—C3—C2117.23 (15)F—C12—C11118.06 (17)
C4—C3—H3121.4F—C12—C13118.91 (17)
C2—C3—H3121.4C11—C12—C13123.02 (17)
C3—C4—C5122.69 (16)C12—C13—C14118.09 (17)
C3—C4—I118.60 (12)C12—C13—H13121.0
C5—C4—I118.71 (13)C14—C13—H13121.0
C6—C5—C4120.44 (16)C13—C14—C9120.72 (17)
C6—C5—H5119.8C13—C14—H14119.6
C4—C5—H5119.8C9—C14—H14119.6
C7—C6—C5116.26 (16)S—C15—H15A109.5
C7—C6—H6121.9S—C15—H15B109.5
C5—C6—H6121.9H15A—C15—H15B109.5
O1—C7—C6125.22 (15)S—C15—H15C109.5
O1—C7—C2110.46 (14)H15A—C15—H15C109.5
C6—C7—C2124.30 (16)H15B—C15—H15C109.5
C1—C8—O1110.43 (14)
O2—S—C1—C8140.15 (15)C1—C2—C7—C6179.85 (16)
C15—S—C1—C8110.45 (17)C2—C1—C8—O10.04 (18)
O2—S—C1—C232.41 (17)S—C1—C8—O1173.80 (12)
C15—S—C1—C276.99 (16)C2—C1—C8—C9178.16 (17)
C8—C1—C2—C70.84 (18)S—C1—C8—C98.1 (3)
S—C1—C2—C7172.87 (13)C7—O1—C8—C10.91 (18)
C8—C1—C2—C3178.44 (18)C7—O1—C8—C9179.46 (13)
S—C1—C2—C37.8 (3)C1—C8—C9—C1428.7 (3)
C7—C2—C3—C40.3 (2)O1—C8—C9—C14149.37 (16)
C1—C2—C3—C4179.47 (17)C1—C8—C9—C10153.29 (19)
C2—C3—C4—C50.3 (2)O1—C8—C9—C1028.6 (2)
C2—C3—C4—I178.89 (11)C14—C9—C10—C110.1 (2)
C3—C4—C5—C60.8 (3)C8—C9—C10—C11178.20 (15)
I—C4—C5—C6178.41 (13)C9—C10—C11—C120.3 (3)
C4—C5—C6—C70.6 (2)C10—C11—C12—F179.46 (16)
C8—O1—C7—C6179.87 (16)C10—C11—C12—C130.2 (3)
C8—O1—C7—C21.47 (18)F—C12—C13—C14178.88 (16)
C5—C6—C7—O1178.21 (15)C11—C12—C13—C140.4 (3)
C5—C6—C7—C20.0 (3)C12—C13—C14—C90.8 (3)
C3—C2—C7—O1177.99 (14)C10—C9—C14—C130.7 (3)
C1—C2—C7—O11.44 (18)C8—C9—C14—C13178.75 (16)
C3—C2—C7—C60.4 (3)
Symmetry code: (i) x+1, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C10—H10···O2ii0.952.533.432 (2)158
Symmetry code: (ii) x+1, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC15H10FIO2S
Mr400.19
Crystal system, space groupTriclinic, P1
Temperature (K)173
a, b, c (Å)8.1045 (2), 8.2699 (2), 11.0999 (3)
α, β, γ (°)94.538 (1), 91.118 (1), 111.982 (1)
V3)686.73 (3)
Z2
Radiation typeMo Kα
µ (mm1)2.49
Crystal size (mm)0.32 × 0.31 × 0.30
Data collection
DiffractometerBruker SMART APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.504, 0.526
No. of measured, independent and
observed [I > 2σ(I)] reflections
12180, 3179, 3130
Rint0.024
(sin θ/λ)max1)0.653
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.018, 0.047, 1.17
No. of reflections3179
No. of parameters182
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.32, 0.90

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
C10—H10···O2i0.952.533.432 (2)157.9
Symmetry code: (i) x+1, y+1, z+1.
 

References

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