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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 67| Part 9| September 2011| Page o2242
doi:10.1107/S160053681103056X

5-(4-Fluoro­phen­yl)-2-methyl-3-methyl­sulfinyl-1-benzo­furan

Pil Ja Seo,a Hong Dae Choi,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 5 July 2011; accepted 29 July 2011; online 2 August 2011)

In the title compound, C16H13FO2S, the 4-fluoro­phenyl ring makes a dihedral angle of 38.75 (8)° with the mean plane of the benzofuran fragment. In the crystal, mol­ecules are linked by weak inter­molecular C—H⋯O hydrogen bonds.

Related literature

For the pharmacological activity of benzofuran compounds, see: Aslam et al. (2009[Aslam, S. N., Stevenson, P. C., Kokubun, T. & Hall, D. R. (2009). Microbiol. Res. 164, 191-195.]); 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.]). For structural studies of related 5-aryl-2-methyl-3-methyl­sulfinyl-1-benzofuran drivatives, see: Choi et al. (2006[Choi, H. D., Seo, P. J., Lee, H. K., Son, B. W. & Lee, U. (2006). Acta Cryst. E62, o4480-o4481.], 2009[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2009). Acta Cryst. E65, o2269.]). For the synthesis of 2-methyl­benzofuran derivatives, see: Choi et al. (1999[Choi, H. D., Seo, P. J. & Son, B. W. (1999). J. Korean Chem. Soc. 43, 237-240.]).

[Scheme 1]

Experimental

Crystal data

  • C16H13FO2S

  • Mr = 288.32

  • Monoclinic, P 21 /c

  • a = 15.101 (5) Å

  • b = 5.3150 (16) Å

  • c = 17.317 (5) Å

  • β = 93.606 (5)°

  • V = 1387.1 (7) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.24 mm−1

  • T = 173 K

  • 0.28 × 0.22 × 0.21 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 = 0.934, Tmax = 0.952

  • 13601 measured reflections

  • 3478 independent reflections

  • 2437 reflections with I > 2σ(I)

  • Rint = 0.055
Refinement

  • R[F2 > 2σ(F2)] = 0.049

  • wR(F2) = 0.137

  • S = 1.05

  • 3478 reflections

  • 183 parameters

  • H-atom parameters constrained

  • Δρmax = 0.32 e Å−3

  • Δρmin = −0.22 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 2.36 3.245 (3) 156
C16—H16B⋯O2ii 0.98 2.43 3.319 (3) 151
Symmetry codes: (i) [x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (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 (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/S160053681103056X/qk2019sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681103056X/qk2019Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681103056X/qk2019Isup3.cml

checkCIF report


Comment top

Recently, many compounds having a benzofuran moiety have drawn much attention owing to their valuable pharmacological properties such as antibacterial and antifungal, antitumor and antiviral, and antimicrobial activities (Aslam et al., 2009, Galal et al., 2009, Khan et al., 2005). These benzofuran derivatives occur in a wide range of natural products (Akgul & Anil, 2003; Soekamto et al., 2003). As a part of our ongoing studies of the substituent effect on the solid state structures of 5-aryl-2-methyl-3-methylsulfinyl-1-benzofuran analogues, see: Choi et al. (2006, 2009), 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 0.011 (2) Å from the least-squares plane defined by the nine constituent atoms. The diheral angle formed by the 4-fluorophenyl ring and the mean plane of the benzofurn fragment is 38.75 (8)°. In the crystal packing (Fig. 2), molecules are linked by weak intermolecular C—H···O hydrogen bonds; the first one between a benzene H atom and the O atom of the sulfinyl group (Table 1; C5—H5···O2i), the second one between a methyl H atom of the methylsulfinyl group and the O atom of the sulfinyl group (Table 1; C16—H16B···O2ii).

Related literature top

For the pharmacological activity of benzofuran compounds, see: Aslam et al. (2009); Galal et al. (2009); Khan et al. (2005). For natural products with benzofuran rings, see: Akgul & Anil (2003); Soekamto et al. (2003). For structural studies of related 5-aryl-2-methyl-3-methylsulfinyl-1-benzofuran drivatives, see: Choi et al. (2006, 2009). For the synthesis of 2-methylbenzofuran derivatives, see: Choi et al. (1999).

Experimental top

5-(4-Fluorophenyl)-2-methyl-3-methylsulfanyl-1-benzofuran was obtained from 4'-fluoro-1,1'-biphenyl-4-ol and α-chloro-α-(methylsufanyl)acetone (Choi et al., 1999). 77% 3-chloroperoxybenzoic acid (291 mg, 1.3 mmol) was added in small portions to a stirred solution of 5-(4-fluorophenyl)-2-methyl-3-methylsulfanyl-1-benzofuran (326 mg, 1.2 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, 1:1 v/v) to afford the title compound as a colorless solid [yield 70%, m.p. 411–413 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 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 and 0.98 Å for methyl H atoms. Uiso(H) = 1.2Ueq(C) for aryl 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. A view of the C—H···O interactions (dotted lines) in the crystal structure of the title compound. [Symmetry codes: (i) x, - y + 1/2, z + 1/2; (ii) x, y + 1, z; (iii) x, - y +1/2 , z - 1/2; (iv) x, y - 1, z.]
5-(4-Fluorophenyl)-2-methyl-3-methylsulfinyl-1-benzofuran top
Crystal data top
C16H13FO2SF(000) = 600
Mr = 288.32Dx = 1.381 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2591 reflections
a = 15.101 (5) Åθ = 2.6–26.4°
b = 5.3150 (16) ŵ = 0.24 mm−1
c = 17.317 (5) ÅT = 173 K
β = 93.606 (5)°Block, colourless
V = 1387.1 (7) Å30.28 × 0.22 × 0.21 mm
Z = 4
Data collection top
Bruker SMART APEXII CCD
diffractometer		3478 independent reflections
Radiation source: rotating anode2437 reflections with I > 2σ(I)
Graphite multilayer monochromatorRint = 0.055
Detector resolution: 10.0 pixels mm-1θmax = 28.5°, θmin = 1.4°
ϕ and ω scansh = −20→20
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		k = −6→7
Tmin = 0.934, Tmax = 0.952l = −22→22
13601 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)] = 0.049Hydrogen site location: difference Fourier map
wR(F2) = 0.137H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0651P)2 + 0.2344P]
where P = (Fo2 + 2Fc2)/3
3478 reflections(Δ/σ)max < 0.001
183 parametersΔρmax = 0.32 e Å−3
0 restraintsΔρmin = −0.22 e Å−3
Crystal data top
C16H13FO2SV = 1387.1 (7) Å3
Mr = 288.32Z = 4
Monoclinic, P21/cMo Kα radiation
a = 15.101 (5) ŵ = 0.24 mm−1
b = 5.3150 (16) ÅT = 173 K
c = 17.317 (5) Å0.28 × 0.22 × 0.21 mm
β = 93.606 (5)°
Data collection top
Bruker SMART APEXII CCD
diffractometer		3478 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		2437 reflections with I > 2σ(I)
Tmin = 0.934, Tmax = 0.952Rint = 0.055
13601 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0490 restraints
wR(F2) = 0.137H-atom parameters constrained
S = 1.05Δρmax = 0.32 e Å−3
3478 reflectionsΔρmin = −0.22 e Å−3
183 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
S10.17563 (4)0.58042 (10)0.28834 (3)0.04103 (18)
F10.55934 (10)−0.3181 (3)0.63856 (9)0.0799 (5)
O10.06789 (11)0.7798 (3)0.47995 (8)0.0601 (5)
O20.19330 (12)0.3052 (3)0.28237 (8)0.0577 (5)
C10.14479 (13)0.6338 (4)0.38282 (10)0.0361 (4)
C20.18189 (13)0.5179 (4)0.45385 (10)0.0348 (4)
C30.25025 (13)0.3517 (3)0.47389 (10)0.0324 (4)
H30.28430.27940.43530.039*
C40.26806 (13)0.2925 (4)0.55191 (10)0.0348 (4)
C50.21503 (16)0.3959 (4)0.60763 (11)0.0509 (6)
H50.22690.35150.66040.061*
C60.14668 (18)0.5585 (5)0.58852 (12)0.0615 (7)
H60.11120.62730.62670.074*
C70.13179 (15)0.6176 (4)0.51116 (12)0.0490 (6)
C80.07767 (15)0.7839 (4)0.40150 (11)0.0472 (5)
C90.34346 (13)0.1263 (4)0.57592 (10)0.0337 (4)
C100.36519 (15)−0.0773 (4)0.53163 (13)0.0471 (5)
H100.3298−0.11450.48580.056*
C110.43708 (18)−0.2285 (5)0.55224 (15)0.0636 (7)
H110.4510−0.36960.52160.076*
C120.48785 (15)−0.1697 (5)0.61814 (13)0.0506 (6)
C130.46903 (15)0.0255 (5)0.66434 (13)0.0518 (6)
H130.50480.05980.71020.062*
C140.39641 (16)0.1737 (4)0.64317 (12)0.0499 (6)
H140.38220.31120.67520.060*
C150.01636 (16)0.9524 (5)0.35532 (14)0.0584 (7)
H15A0.03041.12800.36820.088*
H15B−0.04490.91620.36720.088*
H15C0.02310.92410.30010.088*
C160.28109 (15)0.7332 (4)0.29579 (13)0.0502 (5)
H16A0.31810.65810.33820.075*
H16B0.27290.91270.30610.075*
H16C0.31020.71280.24720.075*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0546 (3)0.0466 (3)0.0211 (2)0.0092 (2)−0.00313 (19)−0.0005 (2)
F10.0614 (9)0.1015 (12)0.0772 (11)0.0432 (9)0.0076 (8)0.0292 (9)
O10.0642 (10)0.0827 (12)0.0348 (8)0.0421 (9)0.0126 (7)0.0095 (8)
O20.0964 (13)0.0440 (9)0.0328 (8)0.0079 (8)0.0051 (8)−0.0095 (6)
C10.0391 (10)0.0436 (11)0.0250 (9)0.0089 (8)−0.0030 (7)0.0015 (8)
C20.0405 (10)0.0402 (10)0.0236 (9)0.0068 (8)0.0020 (7)−0.0002 (8)
C30.0397 (10)0.0355 (9)0.0221 (8)0.0055 (8)0.0030 (7)−0.0021 (7)
C40.0414 (11)0.0377 (10)0.0255 (9)0.0067 (8)0.0030 (8)0.0034 (8)
C50.0663 (15)0.0639 (14)0.0234 (9)0.0235 (12)0.0089 (9)0.0072 (9)
C60.0748 (17)0.0814 (18)0.0303 (11)0.0408 (14)0.0184 (11)0.0079 (11)
C70.0547 (13)0.0611 (14)0.0318 (10)0.0276 (11)0.0077 (9)0.0044 (9)
C80.0509 (13)0.0587 (14)0.0317 (10)0.0169 (11)0.0019 (9)0.0042 (9)
C90.0413 (10)0.0338 (9)0.0263 (9)0.0012 (8)0.0033 (7)0.0064 (7)
C100.0562 (13)0.0401 (11)0.0437 (12)0.0099 (10)−0.0058 (10)−0.0051 (9)
C110.0757 (18)0.0549 (15)0.0602 (15)0.0304 (13)0.0033 (13)−0.0061 (12)
C120.0417 (12)0.0598 (14)0.0506 (13)0.0160 (10)0.0065 (10)0.0224 (11)
C130.0521 (13)0.0600 (14)0.0416 (12)0.0059 (11)−0.0100 (10)0.0124 (11)
C140.0655 (15)0.0508 (12)0.0319 (11)0.0152 (11)−0.0088 (10)0.0006 (9)
C150.0558 (14)0.0726 (17)0.0465 (13)0.0303 (13)0.0010 (11)0.0111 (11)
C160.0527 (13)0.0530 (13)0.0458 (12)0.0110 (11)0.0107 (10)0.0078 (10)
Geometric parameters (Å, º) top
S1—O21.4915 (17)C8—C151.485 (3)
S1—C11.752 (2)C9—C101.378 (3)
S1—C161.785 (2)C9—C141.393 (3)
F1—C121.365 (2)C10—C111.380 (3)
O1—C81.376 (2)C10—H100.9500
O1—C71.379 (2)C11—C121.370 (3)
C1—C81.345 (3)C11—H110.9500
C1—C21.456 (2)C12—C131.351 (3)
C2—C31.386 (3)C13—C141.381 (3)
C2—C71.390 (3)C13—H130.9500
C3—C41.397 (2)C14—H140.9500
C3—H30.9500C15—H15A0.9800
C4—C51.404 (3)C15—H15B0.9800
C4—C91.480 (3)C15—H15C0.9800
C5—C61.371 (3)C16—H16A0.9800
C5—H50.9500C16—H16B0.9800
C6—C71.380 (3)C16—H16C0.9800
C6—H60.9500
O2—S1—C1106.43 (9)C10—C9—C4121.22 (17)
O2—S1—C16106.77 (11)C14—C9—C4121.19 (18)
C1—S1—C1698.46 (10)C9—C10—C11121.6 (2)
C8—O1—C7106.32 (15)C9—C10—H10119.2
C8—C1—C2107.68 (17)C11—C10—H10119.2
C8—C1—S1124.69 (15)C12—C11—C10118.2 (2)
C2—C1—S1127.56 (15)C12—C11—H11120.9
C3—C2—C7119.61 (17)C10—C11—H11120.9
C3—C2—C1136.24 (18)C13—C12—F1118.8 (2)
C7—C2—C1104.13 (17)C13—C12—C11122.7 (2)
C2—C3—C4118.74 (17)F1—C12—C11118.4 (2)
C2—C3—H3120.6C12—C13—C14118.3 (2)
C4—C3—H3120.6C12—C13—H13120.9
C3—C4—C5119.56 (17)C14—C13—H13120.9
C3—C4—C9120.27 (16)C13—C14—C9121.5 (2)
C5—C4—C9120.16 (16)C13—C14—H14119.2
C6—C5—C4122.28 (18)C9—C14—H14119.2
C6—C5—H5118.9C8—C15—H15A109.5
C4—C5—H5118.9C8—C15—H15B109.5
C5—C6—C7116.87 (19)H15A—C15—H15B109.5
C5—C6—H6121.6C8—C15—H15C109.5
C7—C6—H6121.6H15A—C15—H15C109.5
O1—C7—C6126.15 (19)H15B—C15—H15C109.5
O1—C7—C2110.93 (17)S1—C16—H16A109.5
C6—C7—C2122.92 (19)S1—C16—H16B109.5
C1—C8—O1110.93 (17)H16A—C16—H16B109.5
C1—C8—C15132.98 (19)S1—C16—H16C109.5
O1—C8—C15116.06 (18)H16A—C16—H16C109.5
C10—C9—C14117.57 (19)H16B—C16—H16C109.5
O2—S1—C1—C8−137.1 (2)C1—C2—C7—C6−178.9 (2)
C16—S1—C1—C8112.5 (2)C2—C1—C8—O10.9 (3)
O2—S1—C1—C239.1 (2)S1—C1—C8—O1177.74 (16)
C16—S1—C1—C2−71.2 (2)C2—C1—C8—C15178.8 (3)
C8—C1—C2—C3−179.4 (2)S1—C1—C8—C15−4.3 (4)
S1—C1—C2—C33.8 (4)C7—O1—C8—C1−0.5 (3)
C8—C1—C2—C7−0.9 (3)C7—O1—C8—C15−178.8 (2)
S1—C1—C2—C7−177.67 (17)C3—C4—C9—C10−37.6 (3)
C7—C2—C3—C4−1.3 (3)C5—C4—C9—C10143.6 (2)
C1—C2—C3—C4177.1 (2)C3—C4—C9—C14140.8 (2)
C2—C3—C4—C51.9 (3)C5—C4—C9—C14−38.0 (3)
C2—C3—C4—C9−176.79 (18)C14—C9—C10—C11−0.6 (3)
C3—C4—C5—C6−1.3 (4)C4—C9—C10—C11177.9 (2)
C9—C4—C5—C6177.4 (2)C9—C10—C11—C12−0.7 (4)
C4—C5—C6—C70.0 (4)C10—C11—C12—C131.7 (4)
C8—O1—C7—C6179.3 (3)C10—C11—C12—F1−179.7 (2)
C8—O1—C7—C2−0.2 (3)F1—C12—C13—C14−179.8 (2)
C5—C6—C7—O1−178.8 (2)C11—C12—C13—C14−1.2 (4)
C5—C6—C7—C20.7 (4)C12—C13—C14—C9−0.3 (4)
C3—C2—C7—O1179.45 (19)C10—C9—C14—C131.1 (3)
C1—C2—C7—O10.6 (3)C4—C9—C14—C13−177.4 (2)
C3—C2—C7—C6−0.1 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5—H5···O2i0.952.363.245 (3)156
C16—H16B···O2ii0.982.433.319 (3)151
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) x, y+1, z.

Experimental details

Crystal data
Chemical formulaC16H13FO2S
Mr288.32
Crystal system, space groupMonoclinic, P21/c
Temperature (K)173
a, b, c (Å)15.101 (5), 5.3150 (16), 17.317 (5)
β (°) 93.606 (5)
V (Å3)1387.1 (7)
Z4
Radiation typeMo Kα
µ (mm−1)0.24
Crystal size (mm)0.28 × 0.22 × 0.21
Data collection
DiffractometerBruker SMART APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.934, 0.952
No. of measured, independent and
observed [I > 2σ(I)] reflections		13601, 3478, 2437
Rint0.055
(sin θ/λ)max (Å−1)0.671
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.049, 0.137, 1.05
No. of reflections3478
No. of parameters183
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.32, −0.22

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
C5—H5···O2i0.952.363.245 (3)155.8
C16—H16B···O2ii0.982.433.319 (3)150.7
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) x, y+1, z.
 

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ISSN: 2056-9890
Volume 67| Part 9| September 2011| Page o2242
doi:10.1107/S160053681103056X
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