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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 1| January 2010| Page o104
doi:10.1107/S1600536809052519

5-Bromo-2-(4-fluoro­phen­yl)-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 30 November 2009; accepted 7 December 2009; online 12 December 2009)

In the title compound, C15H10BrFO2S, 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, as indicated by a dihedral angle of 26.23 (5)°. The crystal structure is stabilized by a non-classical inter­molecular C—H⋯O hydrogen bond and a Br⋯O halogen bond [3.163 (2) 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 the pharmacological activity of benzofuran compounds, see: Howlett et al. (1999[Howlett, D. R., Perry, A. E., Godfrey, F., Swatton, J. E., Jennings, K. H., Spitzfaden, C., Wadsworth, H., Wood, S. J. & Markwell, R. E. (1999). Biochem. J. 340, 283-289.]); Twyman & Allsop (1999[Twyman, L. J. & Allsop, D. (1999). Tetrahedron Lett. 40, 9383-9384.]). 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 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

  • C15H10BrFO2S

  • Mr = 353.20

  • Triclinic, [P \overline 1]

  • a = 7.8908 (3) Å

  • b = 8.3434 (3) Å

  • c = 10.8349 (5) Å

  • α = 94.886 (2)°

  • β = 91.995 (2)°

  • γ = 111.760 (2)°

  • V = 658.39 (5) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 3.29 mm−1

  • T = 173 K

  • 0.27 × 0.25 × 0.24 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 = 0.470, Tmax = 0.506

  • 11517 measured reflections

  • 3049 independent reflections

  • 2844 reflections with I > 2σ(I)

  • Rint = 0.023
Refinement

  • R[F2 > 2σ(F2)] = 0.025

  • wR(F2) = 0.068

  • S = 1.06

  • 3049 reflections

  • 182 parameters

  • H-atom parameters constrained

  • Δρmax = 1.46 e Å−3

  • Δρmin = −0.41 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C14—H14⋯O2i 0.93 2.58 3.433 (3) 153
Symmetry code: (i) -x+1, -y+1, -z.

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 datablocks global, I. DOI: 10.1107/S1600536809052519/om2304sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809052519/om2304Isup2.hkl

checkCIF report


Comment top

Molecules including benzofuran moiety are of considerable interest due to a variety of their pharmacological activities (Howlett et al., 1999; Twyman & Allsop, 1999) and these compounds are occurring in natural products (Akgul & Anil, 2003; Soekamto et al., 2003). 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 (2) 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 26.23 (5)Å. The crystal packing (Fig. 2) is stabilized by a non-classical intermolecular C—H···O hydrogen bond between the 4-fluorophenyl H atom and the oxygen of the S═O unit, with a C14—H14···O2i (Table 1), and a Br···O halogen bond between the bromine and the oxygen of the S═O unit [Br···O2ii = 3.163 (2) Å; C—Br···O2ii = 173.37 (7)°] (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 the pharmacological activity of benzofuran compounds, see: Howlett et al. (1999); Twyman & Allsop (1999). For natural products with benzofuran ring systems, 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 (179 mg, 0.8 mmol) was added in small portions to a stirred solution of 5-bromo-2-(4-fluorophenyl)-3-methylsulfanyl-1-benzofuran (270 mg, 0.8 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. 498–499 K; Rf = 0.6 (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 = 0.93 Å for aromatic H atoms and 0.96 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—Br···O interactions (dotted lines) in the crystal structure of the title compound. [Symmetry codes: (i) - x + 1, - y + 1, - z; (ii) - x + 1, - y + 1, - z + 1.]
5-Bromo-2-(4-fluorophenyl)-3-methylsulfinyl-1-benzofuran top
Crystal data top
C15H10BrFO2SZ = 2
Mr = 353.20F(000) = 352
Triclinic, P1Dx = 1.782 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.8908 (3) ÅCell parameters from 8308 reflections
b = 8.3434 (3) Åθ = 2.6–27.6°
c = 10.8349 (5) ŵ = 3.29 mm−1
α = 94.886 (2)°T = 173 K
β = 91.995 (2)°Block, colourless
γ = 111.760 (2)°0.27 × 0.25 × 0.24 mm
V = 658.39 (5) Å3
Data collection top
Bruker SMART APEXII CCD
diffractometer		3049 independent reflections
Radiation source: Rotating Anode2844 reflections with I > 2σ(I)
HELIOS monochromatorRint = 0.023
Detector resolution: 10.0 pixels mm-1θmax = 27.6°, θmin = 1.9°
ϕ and ω scansh = −10→10
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		k = −10→10
Tmin = 0.470, Tmax = 0.506l = −14→13
11517 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)] = 0.025Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.068H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0401P)2 + 0.3987P]
where P = (Fo2 + 2Fc2)/3
3049 reflections(Δ/σ)max < 0.001
182 parametersΔρmax = 1.46 e Å−3
0 restraintsΔρmin = −0.41 e Å−3
Crystal data top
C15H10BrFO2Sγ = 111.760 (2)°
Mr = 353.20V = 658.39 (5) Å3
Triclinic, P1Z = 2
a = 7.8908 (3) ÅMo Kα radiation
b = 8.3434 (3) ŵ = 3.29 mm−1
c = 10.8349 (5) ÅT = 173 K
α = 94.886 (2)°0.27 × 0.25 × 0.24 mm
β = 91.995 (2)°
Data collection top
Bruker SMART APEXII CCD
diffractometer		3049 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		2844 reflections with I > 2σ(I)
Tmin = 0.470, Tmax = 0.506Rint = 0.023
11517 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0250 restraints
wR(F2) = 0.068H-atom parameters constrained
S = 1.06Δρmax = 1.46 e Å−3
3049 reflectionsΔρmin = −0.41 e Å−3
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
Br0.59276 (3)0.78959 (2)0.522986 (16)0.02546 (8)
S0.18837 (6)0.20974 (6)0.09974 (4)0.02096 (11)
F−0.07131 (19)0.23126 (17)−0.50519 (11)0.0366 (3)
O10.33521 (19)0.67998 (17)−0.01307 (12)0.0208 (3)
O20.3267 (2)0.18958 (19)0.18682 (15)0.0317 (3)
C10.2611 (3)0.4325 (2)0.07889 (17)0.0188 (3)
C20.3627 (2)0.5753 (2)0.17069 (17)0.0187 (3)
C30.4185 (3)0.5927 (2)0.29638 (17)0.0203 (4)
H30.39110.49690.34100.024*
C40.5166 (3)0.7593 (2)0.35152 (17)0.0206 (4)
C50.5612 (3)0.9066 (2)0.28757 (18)0.0224 (4)
H50.62871.01570.32870.027*
C60.5049 (3)0.8900 (2)0.16288 (18)0.0222 (4)
H60.53200.98580.11830.027*
C70.4070 (3)0.7241 (2)0.10865 (16)0.0193 (3)
C80.2486 (2)0.5018 (2)−0.02943 (17)0.0194 (3)
C90.1628 (3)0.4294 (2)−0.15344 (16)0.0191 (3)
C100.0112 (3)0.2737 (3)−0.17292 (18)0.0232 (4)
H10−0.03750.2150−0.10530.028*
C11−0.0679 (3)0.2050 (3)−0.29139 (19)0.0251 (4)
H11−0.16760.1002−0.30450.030*
C120.0057 (3)0.2968 (3)−0.38902 (17)0.0250 (4)
C130.1530 (3)0.4522 (3)−0.37401 (18)0.0246 (4)
H130.19810.5111−0.44220.029*
C140.2329 (3)0.5193 (2)−0.25552 (17)0.0213 (4)
H140.33290.6240−0.24360.026*
C15−0.0043 (3)0.1923 (3)0.1874 (2)0.0305 (4)
H15A−0.06110.07550.20820.046*
H15B−0.09080.22140.13890.046*
H15C0.03550.27050.26220.046*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br0.03353 (13)0.02421 (11)0.01639 (11)0.00930 (8)−0.00282 (7)−0.00101 (7)
S0.0236 (2)0.0167 (2)0.0229 (2)0.00744 (17)0.00343 (17)0.00380 (17)
F0.0438 (8)0.0409 (7)0.0172 (6)0.0084 (6)−0.0084 (5)0.0006 (5)
O10.0264 (7)0.0196 (6)0.0153 (6)0.0072 (5)−0.0008 (5)0.0030 (5)
O20.0285 (8)0.0287 (7)0.0405 (9)0.0118 (6)−0.0019 (6)0.0135 (6)
C10.0219 (9)0.0174 (8)0.0172 (8)0.0073 (7)0.0020 (7)0.0022 (6)
C20.0209 (9)0.0181 (8)0.0184 (8)0.0085 (7)0.0022 (7)0.0029 (7)
C30.0251 (9)0.0194 (8)0.0178 (8)0.0095 (7)0.0016 (7)0.0033 (7)
C40.0226 (9)0.0238 (9)0.0154 (8)0.0095 (7)0.0000 (7)0.0000 (7)
C50.0244 (9)0.0186 (8)0.0221 (9)0.0063 (7)0.0013 (7)−0.0008 (7)
C60.0258 (9)0.0188 (8)0.0220 (9)0.0073 (7)0.0036 (7)0.0054 (7)
C70.0220 (9)0.0211 (8)0.0152 (8)0.0085 (7)0.0011 (7)0.0025 (7)
C80.0198 (9)0.0186 (8)0.0194 (8)0.0067 (7)0.0020 (7)0.0021 (7)
C90.0222 (9)0.0216 (9)0.0158 (8)0.0109 (7)0.0014 (7)0.0025 (7)
C100.0233 (9)0.0272 (9)0.0186 (9)0.0081 (8)0.0009 (7)0.0056 (7)
C110.0235 (9)0.0250 (9)0.0233 (9)0.0055 (8)−0.0019 (7)0.0024 (7)
C120.0289 (10)0.0313 (10)0.0158 (9)0.0137 (8)−0.0046 (7)−0.0011 (7)
C130.0298 (10)0.0294 (10)0.0168 (9)0.0126 (8)0.0034 (7)0.0066 (7)
C140.0230 (9)0.0227 (9)0.0185 (9)0.0084 (7)0.0024 (7)0.0033 (7)
C150.0285 (10)0.0310 (10)0.0355 (11)0.0124 (9)0.0119 (9)0.0124 (9)
Geometric parameters (Å, º) top
Br—C41.899 (2)C6—C71.376 (3)
Br—O2i3.163 (2)C6—H60.9300
S—O21.484 (2)C8—C91.457 (3)
S—C11.767 (2)C9—C101.395 (3)
S—C151.788 (2)C9—C141.403 (3)
F—C121.355 (2)C10—C111.385 (3)
O1—C81.379 (2)C10—H100.9300
O1—C71.381 (2)C11—C121.376 (3)
C1—C81.368 (2)C11—H110.9300
C1—C21.445 (2)C12—C131.375 (3)
C2—C31.395 (2)C13—C141.385 (3)
C2—C71.397 (2)C13—H130.9300
C3—C41.385 (3)C14—H140.9300
C3—H30.9300C15—H15A0.9600
C4—C51.399 (3)C15—H15B0.9600
C5—C61.386 (3)C15—H15C0.9600
C5—H50.9300
C4—Br—O2i173.37 (7)C1—C8—C9134.25 (17)
O2—S—C1107.27 (9)O1—C8—C9115.24 (15)
O2—S—C15106.10 (10)C10—C9—C14119.18 (17)
C1—S—C1598.44 (9)C10—C9—C8121.53 (17)
C8—O1—C7106.96 (14)C14—C9—C8119.28 (17)
C8—C1—C2107.05 (16)C11—C10—C9121.04 (18)
C8—C1—S126.79 (14)C11—C10—H10119.5
C2—C1—S125.87 (14)C9—C10—H10119.5
C3—C2—C7118.99 (17)C12—C11—C10117.90 (19)
C3—C2—C1135.57 (17)C12—C11—H11121.0
C7—C2—C1105.44 (15)C10—C11—H11121.0
C4—C3—C2116.87 (16)F—C12—C13118.59 (18)
C4—C3—H3121.6F—C12—C11118.35 (18)
C2—C3—H3121.6C13—C12—C11123.06 (18)
C3—C4—C5123.33 (17)C12—C13—C14118.82 (18)
C3—C4—Br118.36 (14)C12—C13—H13120.6
C5—C4—Br118.31 (14)C14—C13—H13120.6
C6—C5—C4119.97 (17)C13—C14—C9119.98 (18)
C6—C5—H5120.0C13—C14—H14120.0
C4—C5—H5120.0C9—C14—H14120.0
C7—C6—C5116.46 (17)S—C15—H15A109.5
C7—C6—H6121.8S—C15—H15B109.5
C5—C6—H6121.8H15A—C15—H15B109.5
C6—C7—O1125.57 (16)S—C15—H15C109.5
C6—C7—C2124.38 (17)H15A—C15—H15C109.5
O1—C7—C2110.04 (15)H15B—C15—H15C109.5
C1—C8—O1110.50 (16)
O2—S—C1—C8141.05 (17)C1—C2—C7—O11.3 (2)
C15—S—C1—C8−109.09 (18)C2—C1—C8—O1−0.1 (2)
O2—S—C1—C2−31.88 (19)S—C1—C8—O1−174.17 (13)
C15—S—C1—C277.98 (18)C2—C1—C8—C9−178.79 (19)
C8—C1—C2—C3178.7 (2)S—C1—C8—C97.2 (3)
S—C1—C2—C3−7.2 (3)C7—O1—C8—C10.9 (2)
C8—C1—C2—C7−0.7 (2)C7—O1—C8—C9179.87 (15)
S—C1—C2—C7173.40 (14)C1—C8—C9—C1026.6 (3)
C7—C2—C3—C4−0.4 (3)O1—C8—C9—C10−152.03 (17)
C1—C2—C3—C4−179.7 (2)C1—C8—C9—C14−154.2 (2)
C2—C3—C4—C5−0.3 (3)O1—C8—C9—C1427.2 (2)
C2—C3—C4—Br179.24 (13)C14—C9—C10—C111.5 (3)
C3—C4—C5—C60.8 (3)C8—C9—C10—C11−179.23 (18)
Br—C4—C5—C6−178.77 (14)C9—C10—C11—C12−1.1 (3)
C4—C5—C6—C7−0.5 (3)C10—C11—C12—F−179.63 (17)
C5—C6—C7—O1178.50 (17)C10—C11—C12—C130.0 (3)
C5—C6—C7—C2−0.2 (3)F—C12—C13—C14−179.66 (17)
C8—O1—C7—C6179.73 (18)C11—C12—C13—C140.7 (3)
C8—O1—C7—C2−1.4 (2)C12—C13—C14—C9−0.3 (3)
C3—C2—C7—C60.7 (3)C10—C9—C14—C13−0.8 (3)
C1—C2—C7—C6−179.82 (18)C8—C9—C14—C13179.95 (16)
C3—C2—C7—O1−178.21 (16)
Symmetry code: (i) −x+1, −y+1, −z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C14—H14···O2ii0.932.583.433 (3)153
Symmetry code: (ii) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formulaC15H10BrFO2S
Mr353.20
Crystal system, space groupTriclinic, P1
Temperature (K)173
a, b, c (Å)7.8908 (3), 8.3434 (3), 10.8349 (5)
α, β, γ (°)94.886 (2), 91.995 (2), 111.760 (2)
V (Å3)658.39 (5)
Z2
Radiation typeMo Kα
µ (mm−1)3.29
Crystal size (mm)0.27 × 0.25 × 0.24
Data collection
DiffractometerBruker SMART APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.470, 0.506
No. of measured, independent and
observed [I > 2σ(I)] reflections		11517, 3049, 2844
Rint0.023
(sin θ/λ)max (Å−1)0.652
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.025, 0.068, 1.06
No. of reflections3049
No. of parameters182
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)1.46, −0.41

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
C14—H14···O2i0.932.583.433 (3)153.3
Symmetry code: (i) −x+1, −y+1, −z.
 

References

First citationAkgul, Y. Y. & Anil, H. (2003). Phytochemistry, 63, 939–943.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationBrandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
 First citationBruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationChoi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2009a). Acta Cryst. E65, o2608.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationChoi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2009b). Acta Cryst. E65, o2649.  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 citationHowlett, D. R., Perry, A. E., Godfrey, F., Swatton, J. E., Jennings, K. H., Spitzfaden, C., Wadsworth, H., Wood, S. J. & Markwell, R. E. (1999). Biochem. J. 340, 283–289.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationPolitzer, P., Lane, P., Concha, M. C., Ma, Y. & Murray, J. S. (2007). J. Mol. Model. 13, 305–311.  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
 First citationTwyman, L. J. & Allsop, D. (1999). Tetrahedron Lett. 40, 9383–9384.  Web of Science CrossRef CAS Google Scholar

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ISSN: 2056-9890
Volume 66| Part 1| January 2010| Page o104
doi:10.1107/S1600536809052519
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