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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 o629
doi:10.1107/S1600536810005581

3-Ethyl­sulfinyl-2-(4-fluoro­phen­yl)-5-iodo-7-methyl-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 1 February 2010; accepted 10 February 2010; online 13 February 2010)

In the title compound, C17H14FIO2S, the 4-fluoro­phenyl ring is rotated out of the benzofuran plane, as indicated by the dihedral angle of 15.60 (6)°. The crystal structure exhibits an I⋯O inter­action [3.052 (2) Å].

Related literature

For the crystal structures of similar 3-ethyl­sulfinyl-2-(4-fluoro­phen­yl)-5-halo-1-benzofuran derivatives, see: Choi et al. (2010a[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010a). Acta Cryst. E66, o323.],b[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010b). Acta Cryst. E66, o402.]). For the pharmacological 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.]). 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

  • C17H14FIO2S

  • Mr = 428.24

  • Triclinic, [P \overline 1]

  • a = 7.4681 (5) Å

  • b = 10.3023 (7) Å

  • c = 10.9761 (7) Å

  • α = 76.289 (1)°

  • β = 89.138 (1)°

  • γ = 74.802 (1)°

  • V = 790.73 (9) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 2.17 mm−1

  • T = 273 K

  • 0.50 × 0.25 × 0.25 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 = 0.520, Tmax = 0.582

  • 6867 measured reflections

  • 3386 independent reflections

  • 3261 reflections with I > 2σ(I)

  • Rint = 0.049
Refinement

  • R[F2 > 2σ(F2)] = 0.022

  • wR(F2) = 0.059

  • S = 1.06

  • 3386 reflections

  • 201 parameters

  • H-atom parameters constrained

  • Δρmax = 0.71 e Å−3

  • Δρmin = −0.81 e Å−3

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

Crystal structure: contains datablock I. DOI: 10.1107/S1600536810005581/pb2023sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810005581/pb2023Isup2.hkl

checkCIF report


Comment top

Compounds containing benzofuran skeleton show diverse pharmacological activities such as antifungal (Aslam et al., 2006), antitumor and antiviral (Galal et al., 2009), antimicrobial (Khan et al., 2005) properties. These compounds widely occur 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 3-ethylsulfinyl-2-(4-fluorophenyl)-5-halo-1-benzofuran analogues (Choi et al., 2010a,b), we report the crystal structure of the title compound (Fig. 1).

The benzofuran unit is essentially planar, with a mean deviation of 0.012 (2) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle formed by the benzofuran plane and the 4-fluorophenyl ring is 15.60 (6)°. The crystal packing (Fig. 2) is stabilized by an I···O halogen bond between the iodine and the oxygen of the S═O unit [C4—I···O2i = 3.052 (2) Å; C4—I···O2i = 168.75 (7)°] (Politzer et al., 2007).

Related literature top

For the crystal structures of similar 3-ethylsulfinyl-2-(4-fluorophenyl)-5-halo-1-benzofuran derivatives, see: Choi et al. (2010a,b). For the pharmacological 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). For a review of halogen bonding, see: Politzer et al. (2007).

Experimental top

77% 3-Chloroperoxybenzoic acid (202 mg, 0.9 mmol) was added in small portions to a stirred solution of 3-ethylsulfanyl-2-(4-fluorophenyl)-5-iodo-7-methyl-1-benzofuran (330 mg, 0.8 mmol) in dichloromethane (25 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, 2:1 v/v) to afford the title compound as a colorless solid [yield 82%, m.p. 466–467 K; Rf = 0.54 (hexane–ethyl acetate, 2:1 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 = 0.93 Å for aryl, 0.97 Å for methylene, and 0.96 Å for methyl H atoms. Uiso(H) = 1.2Ueq (C) for aryl and methylene, 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—I···O interactions (dotted lines) in the crystal structure of the title compound. [Symmetry codes: i) - x + 1, - y + 1, - z + 2.]
3-Ethylsulfinyl-2-(4-fluorophenyl)-5-iodo-7-methyl-1-benzofuran top
Crystal data top
C17H14FIO2SZ = 2
Mr = 428.24F(000) = 420
Triclinic, P1Dx = 1.799 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.4681 (5) ÅCell parameters from 6089 reflections
b = 10.3023 (7) Åθ = 2.1–27.4°
c = 10.9761 (7) ŵ = 2.17 mm−1
α = 76.289 (1)°T = 273 K
β = 89.138 (1)°Block, colourless
γ = 74.802 (1)°0.50 × 0.25 × 0.25 mm
V = 790.73 (9) Å3
Data collection top
Bruker SMART APEXII CCD
diffractometer		3386 independent reflections
Radiation source: Rotating Anode3261 reflections with I > 2σ(I)
Bruker HELIOS graded multilayer optics monochromatorRint = 0.049
Detector resolution: 10.0 pixels mm-1θmax = 27.0°, θmin = 2.8°
ϕ and ω scansh = −9→9
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		k = −13→13
Tmin = 0.520, Tmax = 0.582l = −14→13
6867 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)] = 0.022Hydrogen site location: difference Fourier map
wR(F2) = 0.059H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0284P)2 + 0.4222P]
where P = (Fo2 + 2Fc2)/3
3386 reflections(Δ/σ)max < 0.001
201 parametersΔρmax = 0.71 e Å−3
0 restraintsΔρmin = −0.81 e Å−3
Crystal data top
C17H14FIO2Sγ = 74.802 (1)°
Mr = 428.24V = 790.73 (9) Å3
Triclinic, P1Z = 2
a = 7.4681 (5) ÅMo Kα radiation
b = 10.3023 (7) ŵ = 2.17 mm−1
c = 10.9761 (7) ÅT = 273 K
α = 76.289 (1)°0.50 × 0.25 × 0.25 mm
β = 89.138 (1)°
Data collection top
Bruker SMART APEXII CCD
diffractometer		3386 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		3261 reflections with I > 2σ(I)
Tmin = 0.520, Tmax = 0.582Rint = 0.049
6867 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0220 restraints
wR(F2) = 0.059H-atom parameters constrained
S = 1.06Δρmax = 0.71 e Å−3
3386 reflectionsΔρmin = −0.81 e Å−3
201 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
I0.542549 (19)0.247310 (13)1.062688 (11)0.02504 (6)
F−0.0461 (2)0.7492 (2)−0.01911 (13)0.0441 (4)
O10.2937 (2)0.37876 (15)0.50304 (13)0.0214 (3)
O20.3809 (2)0.75140 (17)0.66534 (15)0.0284 (3)
C10.2629 (3)0.5691 (2)0.57785 (18)0.0204 (4)
C20.3398 (3)0.4484 (2)0.67903 (19)0.0201 (4)
C30.3934 (3)0.4255 (2)0.80613 (18)0.0215 (4)
H30.38240.49820.84470.026*
C40.4640 (3)0.2880 (2)0.87108 (18)0.0215 (4)
C50.4839 (3)0.1760 (2)0.8147 (2)0.0243 (4)
H50.53460.08610.86200.029*
C60.4289 (3)0.1976 (2)0.68911 (19)0.0217 (4)
C70.3574 (3)0.3354 (2)0.62726 (18)0.0205 (4)
C80.2388 (3)0.5210 (2)0.47433 (19)0.0205 (4)
C90.1667 (3)0.5850 (2)0.34449 (19)0.0219 (4)
C100.0601 (3)0.7217 (3)0.3068 (2)0.0284 (5)
H100.03530.77570.36520.034*
C11−0.0100 (3)0.7790 (3)0.1840 (2)0.0313 (5)
H11−0.07910.87100.15870.038*
C120.0261 (3)0.6952 (3)0.1005 (2)0.0298 (5)
C130.1322 (3)0.5599 (3)0.1329 (2)0.0303 (5)
H130.15450.50650.07400.036*
C140.2052 (3)0.5048 (2)0.2553 (2)0.0259 (4)
H140.27990.41420.27850.031*
C150.4396 (4)0.0826 (2)0.6251 (2)0.0295 (5)
H15A0.31630.07790.60720.044*
H15B0.5075−0.00380.67910.044*
H15C0.50180.09990.54820.044*
C160.0218 (3)0.7605 (2)0.6731 (2)0.0279 (4)
H16A−0.07830.74640.62690.034*
H16B0.04670.69080.75200.034*
C17−0.0346 (4)0.9043 (3)0.6981 (2)0.0383 (6)
H17A0.06640.91860.74170.057*
H17B−0.14110.91240.74860.057*
H17C−0.06460.97270.61980.057*
S10.22856 (8)0.74390 (5)0.58266 (4)0.02169 (11)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I0.03433 (10)0.02416 (9)0.01561 (8)−0.00848 (6)−0.00381 (5)−0.00178 (5)
F0.0453 (9)0.0628 (11)0.0171 (6)−0.0101 (8)−0.0098 (6)−0.0001 (6)
O10.0293 (7)0.0200 (7)0.0156 (6)−0.0069 (6)−0.0013 (5)−0.0048 (5)
O20.0352 (9)0.0272 (8)0.0266 (8)−0.0114 (7)−0.0022 (6)−0.0101 (6)
C10.0250 (10)0.0188 (9)0.0174 (9)−0.0055 (8)−0.0002 (7)−0.0046 (7)
C20.0234 (10)0.0188 (9)0.0181 (9)−0.0056 (7)0.0007 (7)−0.0046 (7)
C30.0294 (10)0.0200 (9)0.0166 (9)−0.0077 (8)−0.0010 (7)−0.0057 (7)
C40.0274 (10)0.0222 (10)0.0152 (8)−0.0077 (8)−0.0017 (7)−0.0035 (7)
C50.0302 (11)0.0197 (10)0.0219 (10)−0.0064 (8)−0.0010 (8)−0.0029 (8)
C60.0276 (10)0.0193 (10)0.0200 (9)−0.0077 (8)0.0017 (8)−0.0065 (7)
C70.0244 (10)0.0231 (10)0.0158 (9)−0.0089 (8)0.0006 (7)−0.0052 (7)
C80.0230 (10)0.0196 (9)0.0194 (9)−0.0066 (8)0.0009 (7)−0.0042 (7)
C90.0245 (10)0.0268 (10)0.0161 (9)−0.0107 (8)0.0004 (7)−0.0044 (8)
C100.0329 (12)0.0287 (11)0.0216 (10)−0.0056 (9)−0.0029 (8)−0.0052 (8)
C110.0320 (12)0.0311 (12)0.0249 (11)−0.0049 (10)−0.0045 (9)0.0011 (9)
C120.0272 (11)0.0448 (14)0.0164 (9)−0.0126 (10)−0.0034 (8)−0.0019 (9)
C130.0338 (12)0.0415 (13)0.0197 (10)−0.0137 (10)0.0013 (8)−0.0111 (9)
C140.0276 (11)0.0303 (11)0.0211 (10)−0.0085 (9)−0.0005 (8)−0.0078 (8)
C150.0445 (13)0.0200 (10)0.0263 (10)−0.0089 (9)0.0002 (9)−0.0092 (8)
C160.0291 (11)0.0263 (11)0.0258 (10)−0.0035 (9)0.0021 (8)−0.0055 (8)
C170.0466 (15)0.0275 (12)0.0331 (12)0.0036 (11)0.0038 (11)−0.0076 (10)
S10.0315 (3)0.0166 (2)0.0164 (2)−0.00631 (19)−0.00063 (18)−0.00285 (17)
Geometric parameters (Å, º) top
I—C42.106 (2)C9—C141.405 (3)
I—O2i3.052 (2)C10—C111.387 (3)
F—C121.357 (2)C10—H100.9300
O1—C81.373 (2)C11—C121.380 (4)
O1—C71.380 (2)C11—H110.9300
O2—S11.495 (2)C12—C131.376 (4)
C1—C81.374 (3)C13—C141.387 (3)
C1—C21.449 (3)C13—H130.9300
C1—S11.765 (2)C14—H140.9300
C2—C71.389 (3)C15—H15A0.9600
C2—C31.405 (3)C15—H15B0.9600
C3—C41.391 (3)C15—H15C0.9600
C3—H30.9300C16—C171.520 (3)
C4—C51.407 (3)C16—S11.815 (2)
C5—C61.394 (3)C16—H16A0.9700
C5—H50.9300C16—H16B0.9700
C6—C71.385 (3)C17—H17A0.9600
C6—C151.499 (3)C17—H17B0.9600
C8—C91.465 (3)C17—H17C0.9600
C9—C101.391 (3)
C4—I—O2i168.75 (7)C12—C11—H11121.1
C8—O1—C7106.96 (15)C10—C11—H11121.1
C8—C1—C2106.76 (18)F—C12—C13118.6 (2)
C8—C1—S1126.56 (16)F—C12—C11118.3 (2)
C2—C1—S1126.41 (15)C13—C12—C11123.0 (2)
C7—C2—C3119.10 (19)C12—C13—C14118.5 (2)
C7—C2—C1105.34 (17)C12—C13—H13120.7
C3—C2—C1135.56 (19)C14—C13—H13120.7
C4—C3—C2116.33 (18)C13—C14—C9120.4 (2)
C4—C3—H3121.8C13—C14—H14119.8
C2—C3—H3121.8C9—C14—H14119.8
C3—C4—C5123.00 (18)C6—C15—H15A109.5
C3—C4—I117.95 (15)C6—C15—H15B109.5
C5—C4—I119.06 (15)H15A—C15—H15B109.5
C6—C5—C4121.11 (19)C6—C15—H15C109.5
C6—C5—H5119.4H15A—C15—H15C109.5
C4—C5—H5119.4H15B—C15—H15C109.5
C7—C6—C5114.58 (18)C17—C16—S1109.14 (18)
C7—C6—C15121.77 (18)C17—C16—H16A109.9
C5—C6—C15123.63 (19)S1—C16—H16A109.9
O1—C7—C6123.70 (18)C17—C16—H16B109.9
O1—C7—C2110.45 (18)S1—C16—H16B109.9
C6—C7—C2125.85 (18)H16A—C16—H16B108.3
O1—C8—C1110.48 (17)C16—C17—H17A109.5
O1—C8—C9114.21 (17)C16—C17—H17B109.5
C1—C8—C9135.31 (19)H17A—C17—H17B109.5
C10—C9—C14118.92 (19)C16—C17—H17C109.5
C10—C9—C8122.32 (19)H17A—C17—H17C109.5
C14—C9—C8118.8 (2)H17B—C17—H17C109.5
C11—C10—C9121.3 (2)O2—S1—C1107.96 (10)
C11—C10—H10119.4O2—S1—C16106.52 (10)
C9—C10—H10119.4C1—S1—C1697.83 (11)
C12—C11—C10117.9 (2)
C8—C1—C2—C70.4 (2)C2—C1—C8—O10.4 (2)
S1—C1—C2—C7−173.92 (16)S1—C1—C8—O1174.74 (15)
C8—C1—C2—C3−179.2 (2)C2—C1—C8—C9179.1 (2)
S1—C1—C2—C36.5 (4)S1—C1—C8—C9−6.6 (4)
C7—C2—C3—C40.9 (3)O1—C8—C9—C10162.3 (2)
C1—C2—C3—C4−179.6 (2)C1—C8—C9—C10−16.3 (4)
C2—C3—C4—C50.6 (3)O1—C8—C9—C14−17.0 (3)
C2—C3—C4—I−179.02 (15)C1—C8—C9—C14164.4 (2)
C3—C4—C5—C6−1.5 (4)C14—C9—C10—C110.7 (4)
I—C4—C5—C6178.17 (17)C8—C9—C10—C11−178.6 (2)
C4—C5—C6—C70.7 (3)C9—C10—C11—C121.3 (4)
C4—C5—C6—C15−177.5 (2)C10—C11—C12—F178.2 (2)
C8—O1—C7—C6−178.4 (2)C10—C11—C12—C13−2.0 (4)
C8—O1—C7—C21.4 (2)F—C12—C13—C14−179.7 (2)
C5—C6—C7—O1−179.43 (19)C11—C12—C13—C140.5 (4)
C15—C6—C7—O1−1.2 (3)C12—C13—C14—C91.7 (4)
C5—C6—C7—C20.9 (3)C10—C9—C14—C13−2.3 (3)
C15—C6—C7—C2179.1 (2)C8—C9—C14—C13177.1 (2)
C3—C2—C7—O1178.56 (18)C8—C1—S1—O2−139.72 (19)
C1—C2—C7—O1−1.1 (2)C2—C1—S1—O233.5 (2)
C3—C2—C7—C6−1.7 (3)C8—C1—S1—C16110.0 (2)
C1—C2—C7—C6178.6 (2)C2—C1—S1—C16−76.8 (2)
C7—O1—C8—C1−1.1 (2)C17—C16—S1—O265.53 (18)
C7—O1—C8—C9179.96 (18)C17—C16—S1—C1176.96 (16)
Symmetry code: (i) −x+1, −y+1, −z+2.

Experimental details

Crystal data
Chemical formulaC17H14FIO2S
Mr428.24
Crystal system, space groupTriclinic, P1
Temperature (K)273
a, b, c (Å)7.4681 (5), 10.3023 (7), 10.9761 (7)
α, β, γ (°)76.289 (1), 89.138 (1), 74.802 (1)
V (Å3)790.73 (9)
Z2
Radiation typeMo Kα
µ (mm−1)2.17
Crystal size (mm)0.50 × 0.25 × 0.25
Data collection
DiffractometerBruker SMART APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.520, 0.582
No. of measured, independent and
observed [I > 2σ(I)] reflections		6867, 3386, 3261
Rint0.049
(sin θ/λ)max (Å−1)0.639
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.022, 0.059, 1.06
No. of reflections3386
No. of parameters201
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.71, −0.81

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

 

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ISSN: 2056-9890
Volume 66| Part 3| March 2010| Page o629
doi:10.1107/S1600536810005581
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