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

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ISSN: 2056-9890

2-(4-Chloro­phen­yl)-3-ethyl­sulfinyl-5-fluoro-1-benzo­furan

aDepartment of Chemistry, Dongeui University, San 24 Kaya-dong Busanjin-gu, Busan 614-714, Republic of Korea
*Correspondence e-mail: uklee@pknu.ac.kr

(Received 22 February 2010; accepted 3 March 2010; online 6 March 2010)

In the title compound, C16H12ClFO2S, the 4-chloro­phenyl ring is rotated out of the benzofuran plane, as indicated by the dihedral angle of 19.79 (8)°. The crystal structure exhibits weak inter­molecular C—H⋯O hydrogen bonds and C—H⋯π inter­actions.

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.],c[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010c). Acta Cryst. E66, o629.]). 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.]).

[Scheme 1]

Experimental

Crystal data
  • C16H12ClFO2S

  • Mr = 322.77

  • Monoclinic, P 21 /c

  • a = 11.5257 (9) Å

  • b = 7.9655 (6) Å

  • c = 16.395 (1) Å

  • β = 106.518 (1)°

  • V = 1443.07 (18) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.42 mm−1

  • T = 173 K

  • 0.40 × 0.35 × 0.35 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 = 0.850, Tmax = 0.867

  • 12345 measured reflections

  • 3290 independent reflections

  • 2713 reflections with I > 2σ(I)

  • Rint = 0.028

Refinement
  • R[F2 > 2σ(F2)] = 0.034

  • wR(F2) = 0.085

  • S = 1.05

  • 3290 reflections

  • 191 parameters

  • H-atom parameters constrained

  • Δρmax = 0.29 e Å−3

  • Δρmin = −0.27 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C9–C14 4-chloro­phenyl ring.

D—H⋯A D—H H⋯A DA D—H⋯A
C6—H6⋯O2i 0.93 2.52 3.371 (2) 152
C11—H11⋯O2ii 0.93 2.53 3.116 (2) 121
C15—H15ACgii 0.97 2.66 3.560 (2) 155
Symmetry codes: (i) [x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]; (ii) [-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}].

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

Compounds containing benzofuran moiety 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 are widely occurring 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,c), we report the crystal structure of the title compound (Fig. 1).

The benzofuran unit is essentially planar, with a mean deviation of 0.012 (1) 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 19.79 (8)°. The crystal packing (Fig. 2) is stabilized by two different C—H···O hydrogen bonds; the first between the benzene H atom and the oxygen of the SO unit, with a C6—H6···O2i, and the second between the 4-chlorophenyl H atom and the oxygen of the SO unit, with a C11—H11···O2ii, respectively (Table 1). The crystal packing (Fig. 2) is further stabilized by a C—H···π interaction between the methylene H atom and the 4-chlorophenyl ring, with a C15—H15A···Cgii (Table 1; Cg is the centroid of the C9–C14 4-chlorophenyl ring).

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,c). 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).

Experimental top

77% 3-Chloroperoxybenzoic acid (291 mg, 1.3 mmol) was added in small portions to a stirred solution of 2-(4-chlorophenyl)-3-ethylsulfanyl-5-fluoro-1-benzofuran (368 mg, 1.2 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, 1:1 v/v) to afford the title compound as a colorless solid [yield 79%, m.p. 405–406 K; Rf = 0.64 (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 = 0.93 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 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 small spheres of arbitrary radius.
[Figure 2] Fig. 2. C—H···O and C—H···π interactions (dotted lines) in the crystal structure of the title compound. Cg denotes the ring centroid. [Symmetry codes: (i) x, - y + 3/2, z - 1/2; (ii) - x + 1, y - 1/2, - z + 3/2; (iii) x, - y + 3/2, z + 1/2; (iv) - x + 1, y + 1/2, - z + 3/2.]
2-(4-Chlorophenyl)-3-ethylsulfinyl-5-fluoro-1-benzofuran top
Crystal data top
C16H12ClFO2SF(000) = 664
Mr = 322.77Dx = 1.486 Mg m3
Monoclinic, P21/cMelting point = 405–406 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 11.5257 (9) ÅCell parameters from 5508 reflections
b = 7.9655 (6) Åθ = 2.6–27.4°
c = 16.395 (1) ŵ = 0.42 mm1
β = 106.518 (1)°T = 173 K
V = 1443.07 (18) Å3Block, colourless
Z = 40.40 × 0.35 × 0.35 mm
Data collection top
Bruker SMART APEXII CCD
diffractometer
3290 independent reflections
Radiation source: Rotating Anode2713 reflections with I > 2σ(I)
Bruker HELIOS graded multilayer optics monochromatorRint = 0.028
Detector resolution: 10.0 pixels mm-1θmax = 27.5°, θmin = 1.8°
ϕ and ω scansh = 1414
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
k = 1010
Tmin = 0.850, Tmax = 0.867l = 2120
12345 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)] = 0.034Hydrogen site location: difference Fourier map
wR(F2) = 0.085H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0338P)2 + 0.7418P]
where P = (Fo2 + 2Fc2)/3
3290 reflections(Δ/σ)max < 0.001
191 parametersΔρmax = 0.29 e Å3
0 restraintsΔρmin = 0.27 e Å3
0 constraints
Crystal data top
C16H12ClFO2SV = 1443.07 (18) Å3
Mr = 322.77Z = 4
Monoclinic, P21/cMo Kα radiation
a = 11.5257 (9) ŵ = 0.42 mm1
b = 7.9655 (6) ÅT = 173 K
c = 16.395 (1) Å0.40 × 0.35 × 0.35 mm
β = 106.518 (1)°
Data collection top
Bruker SMART APEXII CCD
diffractometer
3290 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
2713 reflections with I > 2σ(I)
Tmin = 0.850, Tmax = 0.867Rint = 0.028
12345 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0340 restraints
wR(F2) = 0.085H-atom parameters constrained
S = 1.05Δρmax = 0.29 e Å3
3290 reflectionsΔρmin = 0.27 e Å3
191 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl1.01429 (4)0.47181 (6)0.72194 (3)0.03651 (13)
S0.37916 (4)0.44605 (5)0.71678 (2)0.02292 (11)
F0.02836 (9)0.79231 (16)0.49298 (7)0.0447 (3)
O10.45081 (10)0.71492 (14)0.53223 (7)0.0262 (3)
O20.30653 (12)0.54333 (16)0.76279 (8)0.0335 (3)
C10.38345 (15)0.56819 (19)0.62737 (10)0.0228 (3)
C20.28142 (15)0.6562 (2)0.57188 (10)0.0242 (3)
C30.15813 (15)0.6723 (2)0.56551 (11)0.0282 (4)
H30.12310.61780.60280.034*
C40.09200 (16)0.7732 (2)0.50110 (12)0.0321 (4)
C50.13881 (17)0.8572 (2)0.44327 (11)0.0328 (4)
H50.08860.92300.40080.039*
C60.26012 (17)0.8427 (2)0.44906 (11)0.0292 (4)
H60.29420.89690.41120.035*
C70.32842 (15)0.7429 (2)0.51444 (10)0.0249 (3)
C80.48285 (15)0.6093 (2)0.60191 (10)0.0233 (3)
C90.61217 (15)0.5719 (2)0.63190 (10)0.0236 (3)
C100.65770 (15)0.4350 (2)0.68435 (11)0.0262 (4)
H100.60450.36280.70020.031*
C110.78105 (15)0.4052 (2)0.71314 (11)0.0274 (4)
H110.81080.31490.74890.033*
C120.85925 (15)0.5115 (2)0.68801 (11)0.0270 (4)
C130.81697 (16)0.6470 (2)0.63528 (11)0.0308 (4)
H130.87060.71660.61830.037*
C140.69410 (16)0.6776 (2)0.60811 (11)0.0288 (4)
H140.66530.76980.57350.035*
C150.28229 (16)0.2801 (2)0.66061 (11)0.0285 (4)
H15A0.25020.21790.70020.034*
H15B0.21460.32870.61770.034*
C160.3499 (2)0.1613 (2)0.61849 (13)0.0414 (5)
H16A0.38080.22230.57860.062*
H16B0.29590.07500.58910.062*
H16C0.41590.11130.66100.062*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl0.0231 (2)0.0483 (3)0.0378 (3)0.00038 (19)0.00815 (18)0.0005 (2)
S0.0255 (2)0.0234 (2)0.0200 (2)0.00029 (16)0.00665 (15)0.00033 (15)
F0.0275 (6)0.0575 (8)0.0458 (7)0.0124 (5)0.0052 (5)0.0073 (6)
O10.0286 (6)0.0259 (6)0.0249 (6)0.0006 (5)0.0091 (5)0.0030 (5)
O20.0433 (8)0.0313 (7)0.0311 (7)0.0041 (6)0.0192 (6)0.0023 (5)
C10.0251 (8)0.0207 (8)0.0223 (8)0.0015 (6)0.0065 (6)0.0010 (6)
C20.0293 (9)0.0213 (8)0.0218 (8)0.0021 (7)0.0072 (7)0.0013 (6)
C30.0279 (9)0.0302 (9)0.0269 (9)0.0025 (7)0.0085 (7)0.0007 (7)
C40.0275 (9)0.0348 (10)0.0315 (9)0.0059 (8)0.0043 (7)0.0031 (8)
C50.0400 (11)0.0291 (9)0.0246 (9)0.0081 (8)0.0017 (8)0.0012 (7)
C60.0407 (10)0.0249 (9)0.0218 (8)0.0019 (7)0.0086 (7)0.0001 (7)
C70.0284 (9)0.0226 (8)0.0240 (8)0.0017 (7)0.0077 (7)0.0024 (6)
C80.0292 (9)0.0191 (8)0.0218 (8)0.0012 (7)0.0077 (7)0.0008 (6)
C90.0254 (8)0.0234 (8)0.0227 (8)0.0014 (6)0.0080 (7)0.0040 (6)
C100.0264 (9)0.0224 (8)0.0322 (9)0.0027 (7)0.0123 (7)0.0007 (7)
C110.0290 (9)0.0233 (8)0.0300 (9)0.0030 (7)0.0086 (7)0.0006 (7)
C120.0221 (8)0.0329 (9)0.0260 (8)0.0008 (7)0.0070 (7)0.0068 (7)
C130.0303 (9)0.0343 (10)0.0298 (9)0.0074 (8)0.0115 (8)0.0017 (8)
C140.0313 (9)0.0293 (9)0.0258 (9)0.0029 (7)0.0082 (7)0.0037 (7)
C150.0308 (9)0.0234 (8)0.0286 (9)0.0050 (7)0.0038 (7)0.0005 (7)
C160.0585 (13)0.0296 (10)0.0344 (11)0.0016 (9)0.0105 (9)0.0066 (8)
Geometric parameters (Å, º) top
Cl—C121.7427 (17)C8—C91.461 (2)
S—O21.4930 (12)C9—C101.395 (2)
S—C11.7717 (16)C9—C141.401 (2)
S—C151.8047 (17)C10—C111.385 (2)
F—C41.364 (2)C10—H100.9300
O1—C71.375 (2)C11—C121.382 (2)
O1—C81.3820 (19)C11—H110.9300
C1—C81.366 (2)C12—C131.382 (2)
C1—C21.447 (2)C13—C141.380 (2)
C2—C71.395 (2)C13—H130.9300
C2—C31.401 (2)C14—H140.9300
C3—C41.373 (2)C15—C161.512 (3)
C3—H30.9300C15—H15A0.9700
C4—C51.389 (3)C15—H15B0.9700
C5—C61.379 (3)C16—H16A0.9600
C5—H50.9300C16—H16B0.9600
C6—C71.386 (2)C16—H16C0.9600
C6—H60.9300
O2—S—C1106.53 (7)C10—C9—C8122.36 (15)
O2—S—C15106.47 (8)C14—C9—C8119.21 (15)
C1—S—C1597.97 (8)C11—C10—C9120.90 (16)
C7—O1—C8106.91 (12)C11—C10—H10119.5
C8—C1—C2107.11 (14)C9—C10—H10119.5
C8—C1—S127.41 (13)C12—C11—C10119.14 (16)
C2—C1—S125.26 (12)C12—C11—H11120.4
C7—C2—C3118.97 (15)C10—C11—H11120.4
C7—C2—C1105.19 (14)C11—C12—C13121.38 (16)
C3—C2—C1135.83 (16)C11—C12—Cl119.38 (14)
C4—C3—C2116.15 (16)C13—C12—Cl119.23 (14)
C4—C3—H3121.9C14—C13—C12119.14 (16)
C2—C3—H3121.9C14—C13—H13120.4
F—C4—C3117.85 (16)C12—C13—H13120.4
F—C4—C5117.48 (16)C13—C14—C9121.00 (16)
C3—C4—C5124.67 (17)C13—C14—H14119.5
C6—C5—C4119.71 (16)C9—C14—H14119.5
C6—C5—H5120.1C16—C15—S111.53 (13)
C4—C5—H5120.1C16—C15—H15A109.3
C5—C6—C7116.30 (16)S—C15—H15A109.3
C5—C6—H6121.8C16—C15—H15B109.3
C7—C6—H6121.8S—C15—H15B109.3
O1—C7—C6125.43 (15)H15A—C15—H15B108.0
O1—C7—C2110.38 (14)C15—C16—H16A109.5
C6—C7—C2124.18 (16)C15—C16—H16B109.5
C1—C8—O1110.38 (14)H16A—C16—H16B109.5
C1—C8—C9135.43 (15)C15—C16—H16C109.5
O1—C8—C9114.16 (14)H16A—C16—H16C109.5
C10—C9—C14118.43 (16)H16B—C16—H16C109.5
O2—S—C1—C8130.71 (15)C2—C1—C8—O11.44 (18)
C15—S—C1—C8119.40 (16)S—C1—C8—O1176.28 (11)
O2—S—C1—C243.25 (16)C2—C1—C8—C9176.59 (17)
C15—S—C1—C266.64 (15)S—C1—C8—C91.8 (3)
C8—C1—C2—C71.33 (18)C7—O1—C8—C10.97 (17)
S—C1—C2—C7176.32 (12)C7—O1—C8—C9177.52 (13)
C8—C1—C2—C3177.60 (19)C1—C8—C9—C1020.4 (3)
S—C1—C2—C32.6 (3)O1—C8—C9—C10161.65 (14)
C7—C2—C3—C40.7 (2)C1—C8—C9—C14158.99 (19)
C1—C2—C3—C4179.52 (18)O1—C8—C9—C1419.0 (2)
C2—C3—C4—F179.86 (15)C14—C9—C10—C110.8 (2)
C2—C3—C4—C50.3 (3)C8—C9—C10—C11178.60 (15)
F—C4—C5—C6179.66 (16)C9—C10—C11—C121.2 (3)
C3—C4—C5—C60.5 (3)C10—C11—C12—C130.4 (3)
C4—C5—C6—C70.3 (3)C10—C11—C12—Cl178.48 (13)
C8—O1—C7—C6179.89 (16)C11—C12—C13—C140.8 (3)
C8—O1—C7—C20.08 (17)Cl—C12—C13—C14179.64 (14)
C5—C6—C7—O1178.60 (15)C12—C13—C14—C91.2 (3)
C5—C6—C7—C21.4 (3)C10—C9—C14—C130.4 (3)
C3—C2—C7—O1178.38 (14)C8—C9—C14—C13179.81 (16)
C1—C2—C7—O10.77 (18)O2—S—C15—C16174.17 (12)
C3—C2—C7—C61.6 (3)C1—S—C15—C1675.90 (14)
C1—C2—C7—C6179.26 (15)
Hydrogen-bond geometry (Å, º) top
Cg is the centroid of the C9–C14 4-chlorophenyl ring.
D—H···AD—HH···AD···AD—H···A
C6—H6···O2i0.932.523.371 (2)152
C11—H11···O2ii0.932.533.116 (2)121
C15—H15A···Cgii0.972.663.560 (2)155
Symmetry codes: (i) x, y+3/2, z1/2; (ii) x+1, y1/2, z+3/2.

Experimental details

Crystal data
Chemical formulaC16H12ClFO2S
Mr322.77
Crystal system, space groupMonoclinic, P21/c
Temperature (K)173
a, b, c (Å)11.5257 (9), 7.9655 (6), 16.395 (1)
β (°) 106.518 (1)
V3)1443.07 (18)
Z4
Radiation typeMo Kα
µ (mm1)0.42
Crystal size (mm)0.40 × 0.35 × 0.35
Data collection
DiffractometerBruker SMART APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.850, 0.867
No. of measured, independent and
observed [I > 2σ(I)] reflections
12345, 3290, 2713
Rint0.028
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.034, 0.085, 1.05
No. of reflections3290
No. of parameters191
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.29, 0.27

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 C9–C14 4-chlorophenyl ring.
D—H···AD—HH···AD···AD—H···A
C6—H6···O2i0.932.523.371 (2)151.9
C11—H11···O2ii0.932.533.116 (2)121.3
C15—H15A···Cgii0.972.663.560 (2)155.4
Symmetry codes: (i) x, y+3/2, z1/2; (ii) x+1, y1/2, z+3/2.
 

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., Phythian, S. J., Veitch, N. C. & Hall, D. R. (2006). Tetrahedron, 62, 4214–4226.  Web of Science CrossRef 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., Son, B. W. & Lee, U. (2010a). Acta Cryst. E66, o323.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationChoi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010b). Acta Cryst. E66, o402.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationChoi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010c). Acta Cryst. E66, o629.  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

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