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ISSN: 2056-9890

2-(4-Bromo­phen­yl)-5-fluoro-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 21 July 2009; accepted 29 July 2009; online 8 August 2009)

In the title compound, C15H10BrFO2S, the O atom and the methyl group of the methyl­sulfinyl substituent lie on opposite sides of the plane through the benzofuran fragment. The 4-bromo­phenyl ring is rotated out of the benzofuran plane [dihedral angle = 38.98 (8)°], while the structure is stabilized by an inter­molecular C—H⋯O hydrogen bond and a Br⋯O halogen bond [3.036 (2) Å] and has an inter­molecular C–H⋯π inter­action between the 4-bromo­phenyl H atom and the benzene ring of an adjacent benzofuran mol­ecule, as well as aromatic ππ inter­actions between the benzene rings of the benzofuran systems [centroid–centroid distance = 3.482 (3) Å].

Related literature

For the crystal structures of similar 2-(4-bromo­phen­yl)-3-methyl­sulfinyl-1-benzofuran derivatives, see: Choi et al. (2007a[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2007a). Acta Cryst. E63, o3295.],b[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2007b). Acta Cryst. E63, o4282.]). 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 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 = 8.6909 (7) Å

  • b = 9.1765 (7) Å

  • c = 10.1308 (8) Å

  • α = 105.989 (1)°

  • β = 114.811 (1)°

  • γ = 99.423 (1)°

  • V = 667.91 (9) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 3.24 mm−1

  • T = 293 K

  • 0.40 × 0.20 × 0.10 mm

Data collection
  • Bruker SMART CCD-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.461, Tmax = 0.720

  • 5792 measured reflections

  • 2861 independent reflections

  • 2589 reflections with I > 2σ(I)

  • Rint = 0.016

Refinement
  • R[F2 > 2σ(F2)] = 0.024

  • wR(F2) = 0.062

  • S = 1.05

  • 2861 reflections

  • 182 parameters

  • H-atom parameters constrained

  • Δρmax = 0.56 e Å−3

  • Δρmin = −0.52 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C15—H15C⋯O2i 0.96 2.36 3.251 (3) 155
C13—H13⋯Cgii 0.93 2.74 3.366 (3) 125
Symmetry codes: (i) -x+2, -y+2, -z+1; (ii) -x+1, -y+1, -z.

Data collection: SMART (Bruker, 2001[Bruker (2001). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SAINT and SMART. 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

Benzofuran derivatives are of considerable interest because of their pharmacological properties (Howlett et al., 1999; Twyman & Allsop, 1999). This present work is related to our communications on the synthesis and structures of 2-(4-bromophenyl)-3-methylsulfinyl-1-benzofuran analogues, viz. 2-(4-bromophenyl)-5-methyl-3-methylsulfinyl-1-benzofuran (Choi et al., 2007a) and 2-(4-bromophenyl)-5,7-dimethyl-3-methylsulfinyl-1-benzofuran (Choi et al., 2007b). Here we report the crystal structure of the title compound (I) (Fig. 1). The benzofuran unit in (I) is essentially planar, with a mean deviation of 0.006 (2) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle formed by the planes of the benzofuran and the 4-bromophenyl rings is 38.98 (8) °. The crystal packing (Fig. 2) is stabilized by an intermolecular C–H···O hydrogen bond between the methyl H atom and the SO unit (Table 1) and a Br···O halogen bond [Br···O2iii, 3.036 (2) Å; C–Br···O, 165.46 (7) °] (symmetry code : (iii) x, y-1, z-1) (Politzer et al., 2007). The crystal packing also has an intermolecular C–H···π interaction between a 4-bromophenyl H atom (C13) and the benzene ring of an adjacent molecule [C–H···Cgii] (Table 1), (where Cg is the centroid of the C2-C7 benzene ring). Further stability comes from aromatic ππ interactions between the benzene rings of the adjacent molecules, with a Cg···Cgiv distance of 3.482 (3) Å [symmetry code: (iv) -x + 1, -y + 1, -z + 1].

Related literature top

For the crystal structures of similar 2-(4-bromophenyl)-3-methylsulfinyl-1-benzofuran derivatives, see: Choi et al. (2007a,b). For the pharmacological activity of benzofuran compounds, see: Howlett et al. (1999); Twyman & Allsop (1999). For a review of halogen bonding, see: Politzer et al. (2007).

Experimental top

3-Chloroperoxybenzoic acid (77%) (291 mg, 1.3 mmol) was added in small portions to a stirred solution of 2-(4-bromophenyl)-5-fluoro-3-methylsulfanyl-1-benzofuran (310 mg, 1.2 mmol) in dichloromethane (30 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 : 2 (v/v)] to afford the title compound as a colorless solid [yield 81%, m.p. 442-443 K; Rf = 0.68 (hexane-ethyl acetate, 1 : 2 (v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in tetrahydrofuran at room temperature.

Refinement top

All H atoms were positioned geometrically and refined using a riding model, with C–H(aromatic) = 0.93 Å C–H (aliphatic) = 0.96 Å. and with Uiso(H) = 1.2Ueq(C) (aromatic) H atoms and 1.5 Ueq(C) (aliphatic).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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.
[Figure 2] Fig. 2. C–H···O, C–Br···O, C–H···π, and ππ interactions (dotted lines) in the crystal structure of title compound. Cg denotes the ring centroid. [Symmetry codes: (i) - x + 2, - y + 2, - z + 1; (ii) - x + 1, - y + 1, - z; (iii) x, y - 1, z - 1; (iv) - x + 1, - y + 1, - z + 1 (v) x, y + 1, z + 1]. For other codes, see Table 1.
2-(4-Bromophenyl)-5-fluoro-3-methylsulfinyl-1-benzofuran top
Crystal data top
C15H10BrFO2SZ = 2
Mr = 353.20F(000) = 352
Triclinic, P1Dx = 1.756 Mg m3
Hall symbol: -P 1Melting point = 442–443 K
a = 8.6909 (7) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.1765 (7) ÅCell parameters from 4045 reflections
c = 10.1308 (8) Åθ = 2.4–27.5°
α = 105.989 (1)°µ = 3.24 mm1
β = 114.811 (1)°T = 293 K
γ = 99.423 (1)°Block, colorless
V = 667.91 (9) Å30.40 × 0.20 × 0.10 mm
Data collection top
Bruker SMART CCD-detector
diffractometer
2861 independent reflections
Radiation source: fine-focus sealed tube2589 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.016
Detector resolution: 10.0 pixels mm-1θmax = 27.0°, θmin = 2.4°
ϕ and ω scansh = 1111
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 1111
Tmin = 0.461, Tmax = 0.720l = 1212
5792 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)] = 0.024Hydrogen site location: difference Fourier map
wR(F2) = 0.062H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0263P)2 + 0.5235P]
where P = (Fo2 + 2Fc2)/3
2861 reflections(Δ/σ)max = 0.001
182 parametersΔρmax = 0.56 e Å3
0 restraintsΔρmin = 0.52 e Å3
Crystal data top
C15H10BrFO2Sγ = 99.423 (1)°
Mr = 353.20V = 667.91 (9) Å3
Triclinic, P1Z = 2
a = 8.6909 (7) ÅMo Kα radiation
b = 9.1765 (7) ŵ = 3.24 mm1
c = 10.1308 (8) ÅT = 293 K
α = 105.989 (1)°0.40 × 0.20 × 0.10 mm
β = 114.811 (1)°
Data collection top
Bruker SMART CCD-detector
diffractometer
2861 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2589 reflections with I > 2σ(I)
Tmin = 0.461, Tmax = 0.720Rint = 0.016
5792 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0240 restraints
wR(F2) = 0.062H-atom parameters constrained
S = 1.05Δρmax = 0.56 e Å3
2861 reflectionsΔρmin = 0.52 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
Br0.87777 (3)0.07461 (3)0.19442 (3)0.03165 (8)
S0.83195 (6)0.75073 (6)0.37122 (6)0.02170 (11)
F0.27524 (19)0.78610 (17)0.54077 (16)0.0402 (3)
O10.44103 (18)0.34213 (15)0.19174 (16)0.0212 (3)
O20.8984 (2)0.83704 (18)0.54254 (17)0.0315 (3)
C10.6353 (2)0.5929 (2)0.3021 (2)0.0194 (4)
C20.4984 (3)0.5994 (2)0.3476 (2)0.0200 (4)
C30.4642 (3)0.7204 (3)0.4402 (2)0.0249 (4)
H30.53910.82600.49100.030*
C40.3134 (3)0.6731 (3)0.4513 (2)0.0278 (4)
C50.1973 (3)0.5170 (3)0.3795 (3)0.0285 (5)
H50.09690.49350.39140.034*
C60.2324 (3)0.3962 (3)0.2896 (2)0.0262 (4)
H60.15860.29030.24100.031*
C70.3836 (3)0.4430 (2)0.2768 (2)0.0210 (4)
C80.5949 (3)0.4379 (2)0.2100 (2)0.0196 (4)
C90.6748 (2)0.3554 (2)0.1231 (2)0.0194 (4)
C100.6747 (3)0.1994 (2)0.1089 (2)0.0236 (4)
H100.63130.15070.16120.028*
C110.7387 (3)0.1167 (2)0.0176 (2)0.0254 (4)
H110.73860.01300.00830.031*
C120.8029 (3)0.1910 (2)0.0596 (2)0.0219 (4)
C130.8077 (3)0.3461 (2)0.0451 (2)0.0217 (4)
H130.85340.39480.09610.026*
C140.7437 (3)0.4286 (2)0.0465 (2)0.0212 (4)
H140.74660.53300.05700.025*
C150.7267 (3)0.8706 (3)0.2720 (3)0.0310 (5)
H15A0.63310.88800.29500.047*
H15B0.67680.81630.16040.047*
H15C0.81380.97180.30750.047*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br0.04037 (14)0.03169 (13)0.03461 (13)0.01806 (10)0.02714 (11)0.01103 (10)
S0.0186 (2)0.0212 (2)0.0202 (2)0.00384 (18)0.00880 (19)0.00360 (19)
F0.0428 (8)0.0511 (9)0.0360 (7)0.0286 (7)0.0263 (7)0.0104 (6)
O10.0217 (7)0.0186 (6)0.0234 (7)0.0064 (5)0.0122 (6)0.0062 (5)
O20.0288 (8)0.0312 (8)0.0212 (7)0.0001 (6)0.0108 (6)0.0005 (6)
C10.0179 (9)0.0206 (9)0.0180 (9)0.0065 (7)0.0077 (7)0.0065 (7)
C20.0199 (9)0.0245 (10)0.0172 (9)0.0102 (8)0.0086 (7)0.0093 (8)
C30.0252 (10)0.0266 (10)0.0199 (10)0.0111 (8)0.0098 (8)0.0053 (8)
C40.0306 (11)0.0392 (12)0.0200 (10)0.0220 (10)0.0137 (9)0.0119 (9)
C50.0233 (10)0.0449 (13)0.0281 (11)0.0186 (9)0.0150 (9)0.0206 (10)
C60.0221 (10)0.0327 (11)0.0276 (10)0.0097 (8)0.0123 (9)0.0160 (9)
C70.0220 (10)0.0253 (10)0.0183 (9)0.0119 (8)0.0096 (8)0.0098 (8)
C80.0192 (9)0.0215 (9)0.0185 (9)0.0068 (7)0.0088 (7)0.0087 (7)
C90.0186 (9)0.0206 (9)0.0165 (9)0.0070 (7)0.0075 (7)0.0053 (7)
C100.0266 (10)0.0231 (10)0.0253 (10)0.0082 (8)0.0153 (9)0.0106 (8)
C110.0298 (11)0.0204 (9)0.0299 (11)0.0106 (8)0.0170 (9)0.0095 (8)
C120.0208 (9)0.0246 (10)0.0199 (9)0.0096 (8)0.0112 (8)0.0050 (8)
C130.0210 (9)0.0238 (10)0.0183 (9)0.0046 (8)0.0095 (8)0.0072 (8)
C140.0229 (10)0.0175 (9)0.0196 (9)0.0060 (7)0.0084 (8)0.0057 (7)
C150.0287 (11)0.0232 (10)0.0358 (12)0.0059 (9)0.0115 (10)0.0121 (9)
Geometric parameters (Å, º) top
Br—C121.897 (2)C6—C71.384 (3)
Br—O2i3.036 (2)C6—H60.9300
S—C11.771 (2)C8—C91.466 (3)
S—C151.796 (2)C9—C141.398 (3)
F—C41.361 (2)C9—C101.398 (3)
O1—C81.383 (2)C10—C111.388 (3)
O1—C71.386 (2)C10—H100.9300
C1—C81.359 (3)C11—C121.387 (3)
C1—C21.449 (3)C11—H110.9300
C2—C71.391 (3)C12—C131.382 (3)
C2—C31.404 (3)C13—C141.388 (3)
C3—C41.373 (3)C13—H130.9300
C3—H30.9300C14—H140.9300
C4—C51.391 (3)C15—H15A0.9600
C5—C61.392 (3)C15—H15B0.9600
C5—H50.9300C15—H15C0.9600
C12—Br—O2i165.46 (7)C1—C8—C9133.66 (18)
O2—S—C1106.07 (9)O1—C8—C9115.03 (16)
O2—S—C15107.01 (10)C14—C9—C10119.19 (18)
C1—S—C1597.48 (10)C14—C9—C8120.39 (17)
C8—O1—C7105.92 (14)C10—C9—C8120.34 (17)
C8—C1—C2106.94 (17)C11—C10—C9120.58 (18)
C8—C1—S125.96 (15)C11—C10—H10119.7
C2—C1—S126.73 (15)C9—C10—H10119.7
C7—C2—C3119.59 (18)C12—C11—C10119.00 (18)
C7—C2—C1105.25 (16)C12—C11—H11120.5
C3—C2—C1135.15 (19)C10—C11—H11120.5
C4—C3—C2115.79 (19)C13—C12—C11121.53 (18)
C4—C3—H3122.1C13—C12—Br119.15 (15)
C2—C3—H3122.1C11—C12—Br119.28 (15)
F—C4—C3117.9 (2)C12—C13—C14119.28 (18)
F—C4—C5117.34 (19)C12—C13—H13120.4
C3—C4—C5124.73 (19)C14—C13—H13120.4
C4—C5—C6119.66 (19)C13—C14—C9120.40 (18)
C4—C5—H5120.2C13—C14—H14119.8
C6—C5—H5120.2C9—C14—H14119.8
C7—C6—C5116.0 (2)S—C15—H15A109.5
C7—C6—H6122.0S—C15—H15B109.5
C5—C6—H6122.0H15A—C15—H15B109.5
C6—C7—O1125.17 (18)S—C15—H15C109.5
C6—C7—C2124.19 (18)H15A—C15—H15C109.5
O1—C7—C2110.64 (16)H15B—C15—H15C109.5
C1—C8—O1111.24 (16)
O2—S—C1—C8132.93 (17)C1—C2—C7—O10.0 (2)
C15—S—C1—C8116.90 (18)C2—C1—C8—O10.0 (2)
O2—S—C1—C239.08 (19)S—C1—C8—O1173.31 (13)
C15—S—C1—C271.09 (18)C2—C1—C8—C9176.90 (19)
C8—C1—C2—C70.0 (2)S—C1—C8—C99.8 (3)
S—C1—C2—C7173.23 (15)C7—O1—C8—C10.0 (2)
C8—C1—C2—C3179.5 (2)C7—O1—C8—C9177.54 (15)
S—C1—C2—C36.3 (3)C1—C8—C9—C1437.8 (3)
C7—C2—C3—C41.2 (3)O1—C8—C9—C14139.07 (18)
C1—C2—C3—C4179.4 (2)C1—C8—C9—C10145.6 (2)
C2—C3—C4—F179.60 (17)O1—C8—C9—C1037.6 (2)
C2—C3—C4—C50.6 (3)C14—C9—C10—C111.3 (3)
F—C4—C5—C6178.56 (18)C8—C9—C10—C11175.46 (18)
C3—C4—C5—C60.4 (3)C9—C10—C11—C120.0 (3)
C4—C5—C6—C70.8 (3)C10—C11—C12—C131.3 (3)
C5—C6—C7—O1179.26 (17)C10—C11—C12—Br176.36 (15)
C5—C6—C7—C20.2 (3)C11—C12—C13—C141.3 (3)
C8—O1—C7—C6179.56 (19)Br—C12—C13—C14176.41 (14)
C8—O1—C7—C20.0 (2)C12—C13—C14—C90.1 (3)
C3—C2—C7—C60.8 (3)C10—C9—C14—C131.3 (3)
C1—C2—C7—C6179.57 (18)C8—C9—C14—C13175.41 (17)
C3—C2—C7—O1179.62 (16)
Symmetry code: (i) x, y1, z1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C15—H15C···O2ii0.962.363.251 (3)155
C13—H13···Cgiii0.932.743.366 (3)125
Symmetry codes: (ii) x+2, y+2, z+1; (iii) x+1, y+1, z.

Experimental details

Crystal data
Chemical formulaC15H10BrFO2S
Mr353.20
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)8.6909 (7), 9.1765 (7), 10.1308 (8)
α, β, γ (°)105.989 (1), 114.811 (1), 99.423 (1)
V3)667.91 (9)
Z2
Radiation typeMo Kα
µ (mm1)3.24
Crystal size (mm)0.40 × 0.20 × 0.10
Data collection
DiffractometerBruker SMART CCD-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.461, 0.720
No. of measured, independent and
observed [I > 2σ(I)] reflections
5792, 2861, 2589
Rint0.016
(sin θ/λ)max1)0.639
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.024, 0.062, 1.05
No. of reflections2861
No. of parameters182
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.56, 0.52

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), 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
C15—H15C···O2i0.962.363.251 (3)155
C13—H13···Cgii0.932.743.366 (3)125
Symmetry codes: (i) x+2, y+2, z+1; (ii) x+1, y+1, z.
 

References

First citationBrandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany.
First citationBruker (2001). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.
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