Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Previous article
Next article
Previous article
Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Next article

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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 69| Part 8| August 2013| Page o1299
doi:10.1107/S1600536813019867

3-(2-Bromo­phenyl­sulfin­yl)-2,5,7-tri­methyl-1-benzo­furan

Hong Dae Choi,a Pil Ja Seoa 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 25 June 2013; accepted 18 July 2013; online 24 July 2013)

In the title compound, C17H15BrO2S, both the benzo­furan and 2-bromo­phenyl rings are virtually planar, with r.m.s. deviations of 0.009 (2) and 0.006 (2) Å, respectively. The dihedral angle between these mean planes is 89.31 (7)°. In the crystal, mol­ecules are linked via pairs of C—H⋯π inter­actions into inversion dimers. These dimers are further linked by C—H⋯π inter­actions into supra­molecular chains running along the b axis. In addition, C—S⋯π inter­actions, with an S-to-ring-centroid distance of 3.50 (2) Å, are observed between inversion-related dimers.

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2010[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010). Acta Cryst. E66, o472.], 2012[Choi, H. D., Seo, P. J. & Lee, U. (2012). Acta Cryst. E68, o482.]).

[Scheme 1]

Experimental

Crystal data

  • C17H15BrO2S

  • Mr = 363.26

  • Triclinic, [P \overline 1]

  • a = 7.540 (3) Å

  • b = 8.415 (3) Å

  • c = 12.722 (4) Å

  • α = 98.933 (19)°

  • β = 105.001 (19)°

  • γ = 93.530 (18)°

  • V = 765.9 (5) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 2.82 mm−1

  • T = 173 K

  • 0.32 × 0.26 × 0.20 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 = 0.522, Tmax = 0.746

  • 12648 measured reflections

  • 3304 independent reflections

  • 2857 reflections with I > 2σ(I)

  • Rint = 0.038
Refinement

  • R[F2 > 2σ(F2)] = 0.033

  • wR(F2) = 0.085

  • S = 1.12

  • 3304 reflections

  • 193 parameters

  • H-atom parameters constrained

  • Δρmax = 0.29 e Å−3

  • Δρmin = −0.54 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C2–C7 benzene ring and the C1/C2/C7/O1/C8 furan ring, respectively.
D—H⋯A D—H H⋯A D⋯A D—H⋯A
C9—H9C⋯Cg1i 0.98 2.92 3.594 (3) 127
C16—H16⋯Cg2ii 0.95 2.78 3.551 (3) 139
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) x, y+1, z.

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 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) 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/S1600536813019867/fj2637sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813019867/fj2637Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813019867/fj2637Isup3.cml

checkCIF report


Comment top

As a part of our oning study of 2,5,7-trimethyl-1-benzofuran derivatives containing 4-fluorophenylsulfinyl (Choi et al., 2010) and 4-bromophenylsulfinyl (Choi et al., 2012) substituents in 3-postion, we report herein the crystal structure of the title compound.

In the title molecule (Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.009 (2) Å from the least-squares plane defined by the nine constituent atoms. The 2-bromophenyl ring is essentially planar, with a mean deviation of 0.006 (2) Å from the least-squares plane defined by the six constituent atoms. The dihedral angle formed by the mean plane of the benzofuran ring system and the mean plane of the 2-bromophenyl ring is 89.31 (7)°. In the crystal packing (Fig. 2), molecules are linked via pairs of C–H···π interactions (Table 1, Cg1 is the centroid of the C2-C7 benzene ring) into inversion dimers. These dimers are further linked by C–H···π interactions (Table 1, Cg2 is the centroid of C1/C2/C7/O1/C8 furan ring) into supramolecular chains running along the b-axis direction. In addition, there are weak intermolecular S···π interactions between the sulfur atom and the centroid of the 2-bromophenyl ring (C12-C17) of an adjacent molecule, with a S1···Cg3iii being 3.508 (2) Å, resulting in inversion-related dimers.

Related literature top

For background information and the crystal structures of related compounds, see: Choi et al. (2010, 2012).

Experimental top

3-Chloroperoxybenzoic acid (77%, 224 mg, 1.0 mmol) was added in small portions to a stirred solution of 3-(2-bromophenylsulfanyl)-2,5,7-trimethyl-1-benzofuran (312 mg, 0.9 mmol) in dichloromethane (40 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 68%, m.p. 457-458 K; Rf = 0.53 (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 ethyl acetate at room temperature.

Refinement top

All H atoms were positioned geometrically and refined using a riding model, with C–H = 0.95 Å for aryl, 0.99 Å for methyl H atoms, respectively. Uiso(H) = 1.2Ueq(C) for aryl and 1.5Ueq(C) for methyl H atoms. The positions of methyl hydrogens were optimized rotationally.

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, 2012) 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. A view of the C–H···π and C–S···π interactions (dotted lines) in the crystal structure of the title compound. H atoms non-participating in hydrogen-bonding were omitted for clarity. [Symmetry codes: (i) - x + 2, - y + 1, - z + 1; (ii) x, y + 1, z; (iii) - x + 1, - y + 1, - z; (iv) x, y - 1, z.]
3-(2-Bromophenylsulfinyl)-2,5,7-trimethyl-1-benzofuran top
Crystal data top
C17H15BrO2SZ = 2
Mr = 363.26F(000) = 368
Triclinic, P1Dx = 1.575 Mg m−3
Hall symbol: -P 1Melting point = 457–458 K
a = 7.540 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.415 (3) ÅCell parameters from 6758 reflections
c = 12.722 (4) Åθ = 2.7–28.3°
α = 98.933 (19)°µ = 2.82 mm−1
β = 105.001 (19)°T = 173 K
γ = 93.530 (18)°Block, colourless
V = 765.9 (5) Å30.32 × 0.26 × 0.20 mm
Data collection top
Bruker SMART APEXII CCD
diffractometer		3304 independent reflections
Radiation source: rotating anode2857 reflections with I > 2σ(I)
Graphite multilayer monochromatorRint = 0.038
Detector resolution: 10.0 pixels mm-1θmax = 27.0°, θmin = 2.5°
ϕ and ω scansh = −9→9
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		k = −9→10
Tmin = 0.522, Tmax = 0.746l = −16→16
12648 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)] = 0.033Hydrogen site location: difference Fourier map
wR(F2) = 0.085H-atom parameters constrained
S = 1.12 w = 1/[σ2(Fo2) + (0.0362P)2 + 0.4612P]
where P = (Fo2 + 2Fc2)/3
3304 reflections(Δ/σ)max = 0.001
193 parametersΔρmax = 0.29 e Å−3
0 restraintsΔρmin = −0.54 e Å−3
Crystal data top
C17H15BrO2Sγ = 93.530 (18)°
Mr = 363.26V = 765.9 (5) Å3
Triclinic, P1Z = 2
a = 7.540 (3) ÅMo Kα radiation
b = 8.415 (3) ŵ = 2.82 mm−1
c = 12.722 (4) ÅT = 173 K
α = 98.933 (19)°0.32 × 0.26 × 0.20 mm
β = 105.001 (19)°
Data collection top
Bruker SMART APEXII CCD
diffractometer		3304 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		2857 reflections with I > 2σ(I)
Tmin = 0.522, Tmax = 0.746Rint = 0.038
12648 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0330 restraints
wR(F2) = 0.085H-atom parameters constrained
S = 1.12Δρmax = 0.29 e Å−3
3304 reflectionsΔρmin = −0.54 e Å−3
193 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
Br10.37567 (4)0.55880 (4)0.20521 (2)0.03750 (11)
S10.60544 (9)0.28866 (8)0.08301 (5)0.02716 (15)
O10.5429 (2)0.1218 (2)0.34388 (13)0.0266 (4)
O20.7458 (3)0.2104 (2)0.03489 (15)0.0389 (5)
C10.6293 (3)0.2361 (3)0.21447 (19)0.0240 (5)
C20.7898 (3)0.2554 (3)0.30929 (19)0.0241 (5)
C30.9721 (3)0.3263 (3)0.3373 (2)0.0261 (5)
H31.01730.37680.28620.031*
C41.0854 (3)0.3215 (3)0.4414 (2)0.0281 (5)
C51.0155 (4)0.2476 (3)0.5162 (2)0.0310 (6)
H51.09560.24660.58720.037*
C60.8355 (4)0.1761 (3)0.4916 (2)0.0291 (5)
C70.7280 (3)0.1826 (3)0.3862 (2)0.0249 (5)
C80.4873 (3)0.1568 (3)0.2387 (2)0.0258 (5)
C91.2833 (4)0.3978 (4)0.4766 (2)0.0370 (6)
H9A1.30710.45370.41870.056*
H9B1.36670.31350.48830.056*
H9C1.30430.47570.54550.056*
C100.7603 (4)0.0990 (4)0.5728 (2)0.0387 (7)
H10A0.65700.15530.58760.058*
H10B0.85780.10650.64190.058*
H10C0.7173−0.01510.54160.058*
C110.2921 (3)0.1021 (4)0.1772 (2)0.0347 (6)
H11A0.26290.14250.10710.052*
H11B0.21100.14420.22150.052*
H11C0.2734−0.01640.16220.052*
C120.6930 (3)0.5004 (3)0.12476 (18)0.0244 (5)
C130.8517 (3)0.5498 (3)0.0974 (2)0.0290 (5)
H130.91790.47120.06650.035*
C140.9149 (4)0.7125 (3)0.1146 (2)0.0350 (6)
H141.02290.74530.09470.042*
C150.8198 (4)0.8273 (3)0.1610 (2)0.0364 (6)
H150.86270.93890.17280.044*
C160.6626 (4)0.7803 (3)0.1903 (2)0.0338 (6)
H160.59920.85900.22350.041*
C170.5983 (3)0.6167 (3)0.17078 (19)0.0267 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.03110 (16)0.04774 (19)0.04011 (17)0.01447 (12)0.01611 (12)0.01220 (13)
S10.0323 (3)0.0273 (3)0.0219 (3)0.0011 (3)0.0082 (3)0.0035 (2)
O10.0258 (8)0.0286 (9)0.0269 (9)0.0010 (7)0.0092 (7)0.0072 (7)
O20.0568 (12)0.0300 (10)0.0380 (10)0.0081 (9)0.0281 (9)0.0033 (8)
C10.0269 (12)0.0210 (12)0.0247 (12)0.0027 (9)0.0074 (10)0.0046 (9)
C20.0271 (12)0.0218 (12)0.0234 (12)0.0027 (10)0.0079 (10)0.0024 (9)
C30.0280 (12)0.0229 (12)0.0298 (13)0.0013 (10)0.0106 (10)0.0074 (10)
C40.0260 (12)0.0253 (12)0.0320 (13)0.0019 (10)0.0070 (10)0.0038 (10)
C50.0332 (13)0.0327 (14)0.0263 (13)0.0063 (11)0.0049 (11)0.0068 (11)
C60.0330 (13)0.0290 (13)0.0273 (13)0.0053 (11)0.0101 (11)0.0073 (10)
C70.0254 (12)0.0240 (12)0.0273 (12)0.0027 (10)0.0103 (10)0.0052 (10)
C80.0269 (12)0.0233 (12)0.0277 (12)0.0033 (10)0.0092 (10)0.0030 (10)
C90.0273 (13)0.0411 (16)0.0398 (15)0.0011 (12)0.0051 (12)0.0061 (12)
C100.0423 (16)0.0457 (17)0.0326 (15)0.0035 (13)0.0128 (13)0.0163 (13)
C110.0268 (13)0.0398 (16)0.0361 (15)−0.0018 (12)0.0071 (11)0.0072 (12)
C120.0269 (12)0.0274 (12)0.0191 (11)0.0046 (10)0.0039 (9)0.0078 (9)
C130.0296 (13)0.0300 (13)0.0296 (13)0.0062 (11)0.0099 (11)0.0077 (10)
C140.0291 (13)0.0376 (15)0.0368 (15)0.0016 (12)0.0046 (11)0.0099 (12)
C150.0379 (15)0.0276 (14)0.0371 (15)−0.0001 (12)−0.0009 (12)0.0060 (11)
C160.0391 (15)0.0277 (14)0.0305 (14)0.0106 (11)0.0027 (11)0.0018 (11)
C170.0245 (12)0.0334 (14)0.0212 (11)0.0076 (10)0.0027 (10)0.0064 (10)
Geometric parameters (Å, º) top
Br1—C171.896 (3)C9—H9A0.9800
S1—O21.4913 (19)C9—H9B0.9800
S1—C11.763 (2)C9—H9C0.9800
S1—C121.809 (3)C10—H10A0.9800
O1—C81.378 (3)C10—H10B0.9800
O1—C71.392 (3)C10—H10C0.9800
C1—C81.354 (3)C11—H11A0.9800
C1—C21.451 (3)C11—H11B0.9800
C2—C71.392 (3)C11—H11C0.9800
C2—C31.397 (3)C12—C131.388 (3)
C3—C41.386 (4)C12—C171.391 (3)
C3—H30.9500C13—C141.387 (4)
C4—C51.405 (4)C13—H130.9500
C4—C91.512 (4)C14—C151.387 (4)
C5—C61.387 (4)C14—H140.9500
C5—H50.9500C15—C161.384 (4)
C6—C71.387 (4)C15—H150.9500
C6—C101.509 (4)C16—C171.393 (4)
C8—C111.483 (3)C16—H160.9500
O2—S1—C1107.88 (11)H9A—C9—H9C109.5
O2—S1—C12105.17 (11)H9B—C9—H9C109.5
C1—S1—C1299.38 (11)C6—C10—H10A109.5
C8—O1—C7106.49 (18)C6—C10—H10B109.5
C8—C1—C2108.3 (2)H10A—C10—H10B109.5
C8—C1—S1121.31 (19)C6—C10—H10C109.5
C2—C1—S1130.28 (18)H10A—C10—H10C109.5
C7—C2—C3119.3 (2)H10B—C10—H10C109.5
C7—C2—C1104.2 (2)C8—C11—H11A109.5
C3—C2—C1136.5 (2)C8—C11—H11B109.5
C4—C3—C2118.5 (2)H11A—C11—H11B109.5
C4—C3—H3120.8C8—C11—H11C109.5
C2—C3—H3120.8H11A—C11—H11C109.5
C3—C4—C5119.9 (2)H11B—C11—H11C109.5
C3—C4—C9120.8 (2)C13—C12—C17119.0 (2)
C5—C4—C9119.3 (2)C13—C12—S1117.37 (18)
C6—C5—C4123.4 (2)C17—C12—S1123.18 (19)
C6—C5—H5118.3C14—C13—C12120.8 (2)
C4—C5—H5118.3C14—C13—H13119.6
C7—C6—C5114.6 (2)C12—C13—H13119.6
C7—C6—C10122.2 (2)C13—C14—C15119.7 (3)
C5—C6—C10123.2 (2)C13—C14—H14120.2
C6—C7—C2124.4 (2)C15—C14—H14120.2
C6—C7—O1124.9 (2)C16—C15—C14120.4 (3)
C2—C7—O1110.7 (2)C16—C15—H15119.8
C1—C8—O1110.3 (2)C14—C15—H15119.8
C1—C8—C11133.8 (2)C15—C16—C17119.5 (2)
O1—C8—C11115.9 (2)C15—C16—H16120.2
C4—C9—H9A109.5C17—C16—H16120.2
C4—C9—H9B109.5C12—C17—C16120.6 (2)
H9A—C9—H9B109.5C12—C17—Br1121.3 (2)
C4—C9—H9C109.5C16—C17—Br1118.05 (19)
O2—S1—C1—C8−121.0 (2)C8—O1—C7—C6178.3 (2)
C12—S1—C1—C8129.6 (2)C8—O1—C7—C20.0 (2)
O2—S1—C1—C254.9 (3)C2—C1—C8—O10.0 (3)
C12—S1—C1—C2−54.5 (2)S1—C1—C8—O1176.70 (16)
C8—C1—C2—C70.0 (3)C2—C1—C8—C11−179.9 (3)
S1—C1—C2—C7−176.30 (19)S1—C1—C8—C11−3.2 (4)
C8—C1—C2—C3−178.6 (3)C7—O1—C8—C10.0 (3)
S1—C1—C2—C35.1 (4)C7—O1—C8—C11179.9 (2)
C7—C2—C3—C40.1 (3)O2—S1—C12—C135.5 (2)
C1—C2—C3—C4178.5 (3)C1—S1—C12—C13117.0 (2)
C2—C3—C4—C5−0.6 (4)O2—S1—C12—C17177.91 (19)
C2—C3—C4—C9−179.4 (2)C1—S1—C12—C17−70.5 (2)
C3—C4—C5—C60.5 (4)C17—C12—C13—C14−0.5 (4)
C9—C4—C5—C6179.3 (2)S1—C12—C13—C14172.26 (19)
C4—C5—C6—C70.1 (4)C12—C13—C14—C150.8 (4)
C4—C5—C6—C10−179.2 (3)C13—C14—C15—C160.1 (4)
C5—C6—C7—C2−0.7 (4)C14—C15—C16—C17−1.3 (4)
C10—C6—C7—C2178.6 (2)C13—C12—C17—C16−0.7 (3)
C5—C6—C7—O1−178.7 (2)S1—C12—C17—C16−173.02 (19)
C10—C6—C7—O10.6 (4)C13—C12—C17—Br1177.67 (18)
C3—C2—C7—C60.6 (4)S1—C12—C17—Br15.3 (3)
C1—C2—C7—C6−178.3 (2)C15—C16—C17—C121.6 (4)
C3—C2—C7—O1178.9 (2)C15—C16—C17—Br1−176.83 (19)
C1—C2—C7—O10.0 (3)
Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of the C2-C7 benzene ring and the C1/C2/C7/O1/C8 furan ring, respectively.
D—H···AD—HH···AD···AD—H···A
C9—H9C···Cg1i0.982.923.594 (3)127
C16—H16···Cg2ii0.952.783.551 (3)139
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) x, y+1, z.
Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of the C2-C7 benzene ring and the C1/C2/C7/O1/C8 furan ring, respectively.
D—H···AD—HH···AD···AD—H···A
C9—H9C···Cg1i0.982.923.594 (3)127
C16—H16···Cg2ii0.952.783.551 (3)139
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) x, y+1, z.
 

Acknowledgements

This work was supported by the Blue-Bio Industry Regional Innovation Center (RIC08-06-07) at Dongeui University as an RIC program under the Ministry of Knowledge Economy and Busan city.

References

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. & Lee, U. (2012). Acta Cryst. E68, o482.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationChoi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010). Acta Cryst. E66, o472.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationFarrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 69| Part 8| August 2013| Page o1299
doi:10.1107/S1600536813019867
Follow Acta Cryst. E
Sign up for e-alerts
E-alerts
Follow Acta Cryst. on Twitter
Twitter
Follow us on facebook
Facebook
Sign up for RSS feeds
RSS