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 70| Part 7| July 2014| Page o829
https://doi.org/10.1107/S1600536814014810

5-Fluoro-2-(2-fluoro­phen­yl)-3-methyl­sulfinyl-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 23 June 2014; accepted 23 June 2014; online 25 June 2014)

In the title compound, C15H10F2O2S, the dihedral angle between the plane of the benzo­furan ring system (r.m.s. deviation = 0.015 Å) and that of the 2-fluoro­phenyl ring is 28.53 (6)°. In the crystal, mol­ecules are linked by C—H⋯O and C—H⋯F hydrogen bonds, and by π–π inter­actions between the furan and benzene rings of neighbouring mol­ecules [centroid–centroid distance = 3.625 (2) Å], forming a three-dimensional network.

Keywords: crystal structure.

CCDC reference: 1009826

Similar articles

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2009a[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2009a). Acta Cryst. E65, o2084.],b[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2009b). Acta Cryst. E65, o2608.], 2012[Choi, H. D., Seo, P. J. & Lee, U. (2012). Acta Cryst. E68, o3338.]).

[Scheme 1]

Experimental

Crystal data

  • C15H10F2O2S

  • Mr = 292.29

  • Monoclinic, P 21 /c

  • a = 8.6184 (2) Å

  • b = 16.8358 (4) Å

  • c = 9.4019 (2) Å

  • β = 111.254 (1)°

  • V = 1271.40 (5) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.28 mm−1

  • T = 173 K

  • 0.55 × 0.27 × 0.24 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 = 0.863, Tmax = 0.937

  • 12086 measured reflections

  • 3118 independent reflections

  • 2650 reflections with I > 2σ(I)

  • Rint = 0.029
Refinement

  • R[F2 > 2σ(F2)] = 0.038

  • wR(F2) = 0.100

  • S = 1.07

  • 3118 reflections

  • 182 parameters

  • H-atom parameters constrained

  • Δρmax = 0.31 e Å−3

  • Δρmin = −0.40 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C5—H5⋯O2i 0.95 2.52 3.343 (2) 145
C12—H12⋯O2ii 0.95 2.39 3.326 (2) 166
C15—H15A⋯F1iii 0.98 2.54 3.419 (2) 149
Symmetry codes: (i) [-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]; (ii) x-1, y, z-1; (iii) -x+2, -y+1, -z+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 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

CCDC reference: 1009826

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S1600536814014810/bt6985sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536814014810/bt6985Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536814014810/bt6985Isup3.cml

checkCIF report


Comment top

As a part of our ongoing project of 5-fluoro-3-methylsulfinyl-1-benzofuran derivatives containing 4-bromophenyl (Choi et al., 2009a), 4-fluorophenyl (Choi et al., 2009b) and 4-methylphenyl (Choi et al., 2012) substituents in 2-position, we report herein on the crystal structure of the title compound.

In the title molecule (Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.015 (1) Å from the least-squares plane defined by the nine constituent atoms. The 2-fluorophenyl ring is essentially planar, with a mean deviation of 0.053 (1) Å from the least-squares plane defined by the six constituent atoms. The dihedral angle formed by the benzofuran ring system and the 2-fluorophenyl ring is 28.53 (6)°. In the crystal structure (Fig. 2), molecules are inked by C—H···O and C—H···F hydrogen bonds (Table 1), and by π–π interactions between the furan and benzene rings of neighbouring molecules, with a Cg1···Cg2iv distance of 3.625 (2) Å and an interplanar distance of 3.295 (2) Å resulting in a slippage of 1.511 (2) Å (Cg1 and Cg2 are the centroids of the C1/C2/C7/O1/C8 furan ring and the C2–C7 benzene ring, respectively), forming a three-dimensional network.

Related literature top

For background information and the crystal structures of related compounds, see: Choi et al. (2009a,b, 2012).

Experimental top

3-Chloroperoxybenzoic acid (77%, 269 mg, 1.2 mmol) was added in small portions to a stirred solution of 5-fluoro-2-(2-fluorophenyl)-3-methylsulfanyl-1-benzofuran (304 mg, 1.1 mmol) in dichloromethane (35 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 73%, m.p. 412–413 K; Rf = 0.46 (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 = 0.95 Å for aryl and 0.98 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 using the SHELXL-97 command AFIX 137 (Sheldrick, 2008).

Structure description top

As a part of our ongoing project of 5-fluoro-3-methylsulfinyl-1-benzofuran derivatives containing 4-bromophenyl (Choi et al., 2009a), 4-fluorophenyl (Choi et al., 2009b) and 4-methylphenyl (Choi et al., 2012) substituents in 2-position, we report herein on the crystal structure of the title compound.

In the title molecule (Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.015 (1) Å from the least-squares plane defined by the nine constituent atoms. The 2-fluorophenyl ring is essentially planar, with a mean deviation of 0.053 (1) Å from the least-squares plane defined by the six constituent atoms. The dihedral angle formed by the benzofuran ring system and the 2-fluorophenyl ring is 28.53 (6)°. In the crystal structure (Fig. 2), molecules are inked by C—H···O and C—H···F hydrogen bonds (Table 1), and by π–π interactions between the furan and benzene rings of neighbouring molecules, with a Cg1···Cg2iv distance of 3.625 (2) Å and an interplanar distance of 3.295 (2) Å resulting in a slippage of 1.511 (2) Å (Cg1 and Cg2 are the centroids of the C1/C2/C7/O1/C8 furan ring and the C2–C7 benzene ring, respectively), forming a three-dimensional network.

For background information and the crystal structures of related compounds, see: Choi et al. (2009a,b, 2012).

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 for Windows (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 molecule with the atom numbering scheme The displacement ellipsoids are drawn at the 50% probability level. The hydrogen atoms are presented as small spheres of arbitrary radius.
[Figure 2] Fig. 2. A view of the C—H···O, C—H···F and π–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 - 1/2, - z + 3/2; (ii) x - 1, y, z -1; (iii) - x + 2, - y + 1, - z + 2; (iv) - x + 2, - y + 1, - z + 1; (v) - x + 1, y + 1/2, - z + 3/2; (vi) x + 1, y, z + 1.]
5-Fluoro-2-(2-fluorophenyl)-3-methylsulfinyl-1-benzofuran top
Crystal data top
C15H10F2O2SF(000) = 600
Mr = 292.29Dx = 1.527 Mg m−3
Monoclinic, P21/cMelting point = 413–412 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 8.6184 (2) ÅCell parameters from 4357 reflections
b = 16.8358 (4) Åθ = 2.4–27.8°
c = 9.4019 (2) ŵ = 0.28 mm−1
β = 111.254 (1)°T = 173 K
V = 1271.40 (5) Å3Block, colourless
Z = 40.55 × 0.27 × 0.24 mm
Data collection top
Bruker SMART APEXII CCD
diffractometer		3118 independent reflections
Radiation source: rotating anode2650 reflections with I > 2σ(I)
Graphite multilayer monochromatorRint = 0.029
Detector resolution: 10.0 pixels mm-1θmax = 28.3°, θmin = 2.4°
φ and ω scansh = −10→11
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		k = −22→19
Tmin = 0.863, Tmax = 0.937l = −12→12
12086 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)] = 0.038Hydrogen site location: difference Fourier map
wR(F2) = 0.100H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0492P)2 + 0.3389P]
where P = (Fo2 + 2Fc2)/3
3118 reflections(Δ/σ)max = 0.001
182 parametersΔρmax = 0.31 e Å−3
0 restraintsΔρmin = −0.40 e Å−3
Crystal data top
C15H10F2O2SV = 1271.40 (5) Å3
Mr = 292.29Z = 4
Monoclinic, P21/cMo Kα radiation
a = 8.6184 (2) ŵ = 0.28 mm−1
b = 16.8358 (4) ÅT = 173 K
c = 9.4019 (2) Å0.55 × 0.27 × 0.24 mm
β = 111.254 (1)°
Data collection top
Bruker SMART APEXII CCD
diffractometer		3118 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		2650 reflections with I > 2σ(I)
Tmin = 0.863, Tmax = 0.937Rint = 0.029
12086 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0380 restraints
wR(F2) = 0.100H-atom parameters constrained
S = 1.07Δρmax = 0.31 e Å−3
3118 reflectionsΔρmin = −0.40 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
S10.71915 (5)0.69054 (2)0.61445 (4)0.02927 (12)
F11.13845 (13)0.42819 (7)0.91201 (11)0.0485 (3)
F20.38183 (11)0.67630 (6)0.41827 (10)0.0374 (2)
O10.67546 (12)0.49850 (6)0.36067 (11)0.0281 (2)
O20.89953 (15)0.70691 (7)0.69905 (14)0.0431 (3)
C10.71116 (17)0.59444 (8)0.53646 (16)0.0234 (3)
C20.82307 (17)0.53035 (9)0.60821 (17)0.0250 (3)
C30.94153 (18)0.51622 (10)0.75344 (17)0.0299 (3)
H30.96320.55340.83440.036*
C41.02416 (19)0.44539 (10)0.77150 (18)0.0336 (4)
C51.0016 (2)0.38969 (10)0.6577 (2)0.0361 (4)
H51.06500.34210.67850.043*
C60.8859 (2)0.40384 (9)0.5134 (2)0.0330 (3)
H60.86810.36730.43200.040*
C70.79767 (17)0.47404 (9)0.49421 (17)0.0267 (3)
C80.62565 (17)0.57246 (9)0.38947 (16)0.0242 (3)
C90.49420 (17)0.60820 (9)0.25958 (16)0.0254 (3)
C100.37363 (18)0.65773 (9)0.27581 (17)0.0271 (3)
C110.24304 (19)0.68798 (10)0.15475 (19)0.0324 (3)
H110.16260.72150.17130.039*
C120.2317 (2)0.66846 (11)0.00904 (19)0.0382 (4)
H120.14260.6886−0.07640.046*
C130.3500 (2)0.61954 (12)−0.01285 (19)0.0417 (4)
H130.34180.6064−0.11360.050*
C140.4797 (2)0.58969 (11)0.10995 (18)0.0351 (4)
H140.56010.55620.09300.042*
C150.6325 (2)0.66632 (12)0.7563 (2)0.0435 (4)
H15A0.69840.62390.82210.065*
H15B0.51730.64840.70600.065*
H15C0.63470.71350.81810.065*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0313 (2)0.0205 (2)0.0279 (2)0.00149 (14)0.00106 (15)−0.00264 (14)
F10.0421 (6)0.0544 (7)0.0399 (6)0.0162 (5)0.0039 (5)0.0204 (5)
F20.0311 (5)0.0469 (6)0.0322 (5)0.0074 (4)0.0092 (4)−0.0046 (4)
O10.0285 (5)0.0232 (5)0.0278 (5)0.0023 (4)0.0045 (4)−0.0042 (4)
O20.0356 (6)0.0315 (7)0.0463 (7)−0.0063 (5)−0.0041 (5)−0.0079 (5)
C10.0240 (7)0.0200 (7)0.0239 (7)−0.0001 (5)0.0060 (5)0.0002 (5)
C20.0239 (7)0.0225 (7)0.0278 (7)0.0003 (5)0.0085 (6)0.0026 (6)
C30.0289 (7)0.0308 (8)0.0271 (8)0.0014 (6)0.0068 (6)0.0047 (6)
C40.0273 (7)0.0373 (9)0.0332 (8)0.0043 (6)0.0073 (6)0.0148 (7)
C50.0333 (8)0.0262 (8)0.0509 (10)0.0080 (6)0.0177 (7)0.0123 (7)
C60.0354 (8)0.0223 (8)0.0426 (9)0.0026 (6)0.0155 (7)0.0013 (7)
C70.0256 (7)0.0234 (7)0.0293 (8)0.0004 (6)0.0079 (6)0.0026 (6)
C80.0233 (7)0.0207 (7)0.0269 (7)−0.0001 (5)0.0071 (6)−0.0013 (6)
C90.0229 (7)0.0235 (7)0.0251 (7)−0.0021 (5)0.0029 (5)−0.0002 (6)
C100.0250 (7)0.0253 (7)0.0277 (7)−0.0033 (6)0.0056 (6)−0.0001 (6)
C110.0247 (7)0.0280 (8)0.0398 (9)0.0000 (6)0.0059 (6)0.0058 (7)
C120.0305 (8)0.0389 (10)0.0333 (9)−0.0031 (7)−0.0027 (7)0.0103 (7)
C130.0409 (9)0.0522 (11)0.0237 (8)−0.0017 (8)0.0020 (7)0.0002 (7)
C140.0332 (8)0.0390 (10)0.0286 (8)0.0031 (7)0.0059 (6)−0.0041 (7)
C150.0510 (11)0.0494 (11)0.0300 (9)0.0126 (9)0.0143 (8)−0.0051 (8)
Geometric parameters (Å, º) top
S1—O21.4930 (12)C6—C71.381 (2)
S1—C11.7675 (14)C6—H60.9500
S1—C151.7952 (18)C8—C91.461 (2)
F1—C41.3623 (18)C9—C101.383 (2)
F2—C101.3521 (17)C9—C141.402 (2)
O1—C81.3757 (17)C10—C111.376 (2)
O1—C71.3772 (18)C11—C121.377 (2)
C1—C81.3606 (19)C11—H110.9500
C1—C21.441 (2)C12—C131.383 (3)
C2—C71.388 (2)C12—H120.9500
C2—C31.397 (2)C13—C141.378 (2)
C3—C41.368 (2)C13—H130.9500
C3—H30.9500C14—H140.9500
C4—C51.383 (3)C15—H15A0.9800
C5—C61.382 (2)C15—H15B0.9800
C5—H50.9500C15—H15C0.9800
O2—S1—C1105.45 (7)C1—C8—C9135.03 (14)
O2—S1—C15106.22 (8)O1—C8—C9114.27 (12)
C1—S1—C1597.82 (8)C10—C9—C14116.59 (14)
C8—O1—C7106.33 (11)C10—C9—C8122.83 (13)
C8—C1—C2107.22 (13)C14—C9—C8120.49 (14)
C8—C1—S1126.55 (11)F2—C10—C11117.86 (14)
C2—C1—S1124.91 (11)F2—C10—C9118.49 (13)
C7—C2—C3119.55 (14)C11—C10—C9123.63 (14)
C7—C2—C1104.98 (13)C10—C11—C12118.45 (15)
C3—C2—C1135.45 (14)C10—C11—H11120.8
C4—C3—C2115.65 (15)C12—C11—H11120.8
C4—C3—H3122.2C11—C12—C13119.99 (15)
C2—C3—H3122.2C11—C12—H12120.0
F1—C4—C3117.82 (15)C13—C12—H12120.0
F1—C4—C5117.12 (14)C14—C13—C12120.69 (16)
C3—C4—C5125.06 (15)C14—C13—H13119.7
C6—C5—C4119.46 (15)C12—C13—H13119.7
C6—C5—H5120.3C13—C14—C9120.65 (16)
C4—C5—H5120.3C13—C14—H14119.7
C7—C6—C5116.30 (15)C9—C14—H14119.7
C7—C6—H6121.9S1—C15—H15A109.5
C5—C6—H6121.9S1—C15—H15B109.5
O1—C7—C6125.31 (14)H15A—C15—H15B109.5
O1—C7—C2110.75 (12)S1—C15—H15C109.5
C6—C7—C2123.93 (14)H15A—C15—H15C109.5
C1—C8—O1110.69 (12)H15B—C15—H15C109.5
O2—S1—C1—C8−131.06 (13)C1—C2—C7—C6177.33 (14)
C15—S1—C1—C8119.65 (14)C2—C1—C8—O1−0.41 (16)
O2—S1—C1—C234.10 (14)S1—C1—C8—O1166.89 (10)
C15—S1—C1—C2−75.19 (14)C2—C1—C8—C9178.28 (15)
C8—C1—C2—C71.30 (15)S1—C1—C8—C9−14.4 (2)
S1—C1—C2—C7−166.26 (11)C7—O1—C8—C1−0.67 (15)
C8—C1—C2—C3179.85 (16)C7—O1—C8—C9−179.65 (12)
S1—C1—C2—C312.3 (2)C1—C8—C9—C10−31.3 (3)
C7—C2—C3—C4−0.5 (2)O1—C8—C9—C10147.36 (14)
C1—C2—C3—C4−178.85 (16)C1—C8—C9—C14152.31 (17)
C2—C3—C4—F1−178.67 (13)O1—C8—C9—C14−29.0 (2)
C2—C3—C4—C51.7 (2)C14—C9—C10—F2179.21 (13)
F1—C4—C5—C6179.35 (14)C8—C9—C10—F22.7 (2)
C3—C4—C5—C6−1.0 (3)C14—C9—C10—C110.7 (2)
C4—C5—C6—C7−0.9 (2)C8—C9—C10—C11−175.83 (14)
C8—O1—C7—C6−177.54 (14)F2—C10—C11—C12−178.95 (14)
C8—O1—C7—C21.55 (16)C9—C10—C11—C12−0.4 (2)
C5—C6—C7—O1−178.87 (14)C10—C11—C12—C130.0 (3)
C5—C6—C7—C22.2 (2)C11—C12—C13—C140.2 (3)
C3—C2—C7—O1179.41 (12)C12—C13—C14—C90.1 (3)
C1—C2—C7—O1−1.76 (16)C10—C9—C14—C13−0.5 (2)
C3—C2—C7—C6−1.5 (2)C8—C9—C14—C13176.09 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5—H5···O2i0.952.523.343 (2)145
C12—H12···O2ii0.952.393.326 (2)166
C15—H15A···F1iii0.982.543.419 (2)149
Symmetry codes: (i) −x+2, y−1/2, −z+3/2; (ii) x−1, y, z−1; (iii) −x+2, −y+1, −z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5—H5···O2i0.952.523.343 (2)145.3
C12—H12···O2ii0.952.393.326 (2)166.4
C15—H15A···F1iii0.982.543.419 (2)149.4
Symmetry codes: (i) −x+2, y−1/2, −z+3/2; (ii) x−1, y, z−1; (iii) −x+2, −y+1, −z+2.
 

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, o3338.  CSD CrossRef IUCr Journals Google Scholar
 First citationChoi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2009a). Acta Cryst. E65, o2084.  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, o2608.  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 70| Part 7| July 2014| Page o829
https://doi.org/10.1107/S1600536814014810
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