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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 68| Part 8| August 2012| Page o2477
https://doi.org/10.1107/S1600536812031972

5-Fluoro-3-(3-fluoro­phenyl­sulfon­yl)-2-methyl-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 9 July 2012; accepted 13 July 2012; online 18 July 2012)

In the title compound, C15H10F2O3S, the 3-fluoro­phenyl ring makes a dihedral angle of 79.51 (6)° with the mean plane [r.m.s. deviation = 0.006 (2) Å] of the benzofuran fragment. In the crystal, mol­ecules are linked by weak C—H⋯F and C—H⋯O hydrogen bonds. The crystal structure also exhibits slipped π–π inter­actions between the benzene and furan rings of neighbouring mol­ecules [centroid–centroid distances = 3.563 (3) and 3.820 (3) Å and slippages of 0.358 (3)and 1.551 (3) Å]. In the 3-fluoro­phenyl ring, the F atom is disordered over two positions with site-occupancy factors of 0.887 (3) and 0.113 (3).

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, o1909.], 2012[Choi, H. D., Seo, P. J. & Lee, U. (2012). Acta Cryst. E68, o455.]).

[Scheme 1]

Experimental

Crystal data

  • C15H10F2O3S

  • Mr = 308.29

  • Monoclinic, P 21 /n

  • a = 7.2772 (2) Å

  • b = 11.0972 (3) Å

  • c = 16.5625 (5) Å

  • β = 100.698 (2)°

  • V = 1314.28 (6) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.28 mm−1

  • T = 296 K

  • 0.30 × 0.22 × 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 = 0.663, Tmax = 0.746

  • 12792 measured reflections

  • 3275 independent reflections

  • 2732 reflections with I > 2σ(I)

  • Rint = 0.032
Refinement

  • R[F2 > 2σ(F2)] = 0.037

  • wR(F2) = 0.104

  • S = 1.04

  • 3275 reflections

  • 202 parameters

  • 14 restraints

  • H-atom parameters constrained

  • Δρmax = 0.36 e Å−3

  • Δρmin = −0.31 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C5—H5⋯F2i 0.93 2.45 3.302 (2) 153
C15—H15⋯O3ii 0.93 2.47 3.3754 (19) 165
Symmetry codes: (i) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (ii) [-x+{\script{1\over 2}}, 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

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812031972/pk2432sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812031972/pk2432Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812031972/pk2432Isup3.cml

checkCIF report


Comment top

As a part of our continuing study of 5-fluoro-2-methyl-1-benzofuran derivatives containing 3-(4-fluorophenylsulfonyl) (Choi et al., 2010) and 3-(4-methylphenylsulfonyl) (Choi et al., 2012) substituents, 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 0.006 (2) Å from the least-squares plane defined by the nine constituent atoms. In the 3-fluorophenyl ring, the F atom is disordered over two positions with site-occupancy factors, from refinement of 0.887 (3) (part A) and 0.113 (3) (part B). The dihedral angle between the 3-fluorophenyl ring and the mean plane of the benzofuran ring is 79.51 (6)°. In the crystal structure (Fig. 2), molecules are connected by weak intermolecular C–H···F and C–H···O hydrogen bonds (Table 1). The crystal packing (Fig. 3) also exhibits slipped π–π interactions between the benzene and furan rings of neighbouring molecules, with Cg1···Cg2iii and Cg1···Cg2iv distances of 3.563 (3) Å & 3.820 (3) Å, and interplanar distances of 3.545 (3) Å & 3.491 (3) Å resulting in slippages of 0.358 (3) Å & 1.551 (3) Å (Cg1 and Cg2 are the centroids of the C2-C7 benzene ring and the C1/C2/C7/O1/C8 furan ring, respectively).

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%, 515 mg, 2.3 mmol) was added in small portions to a stirred solution of 5-fluoro-3-(3-fluorophenylsulfanyl)-2-methyl-1-benzofuran (304 mg, 1.1 mmol) in dichloromethane (50 mL) at 273 K. After being stirred at room temperature for 10h, 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 (benzene) to afford the title compound as a colorless solid [yield 73%, m.p. 443-444 K; Rf = 0.66 (benzene)]. 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 = 0.93 Å for aryl and 0.96 Å for methyl H atoms. Uiso(H) = 1.2Ueq(C) for aryl and 1.5Ueq(C) for methyl H atoms. The positions of methyl hydrogens were optimized rotationally. The F2 atom of the 3-fluorophenyl ring is disordered over two positions with site occupancy factors, from refinement of 0.887 (3) (part A) and 0.113 (3) (part B). The distance of equivalent C-F pairs were restrained to 1.330 (5) Å using the SHELXL-97 command DFIX, and displacement ellipsoids of F2 set were restrained using the SHELXL-97 command ISOR.

Structure description top

As a part of our continuing study of 5-fluoro-2-methyl-1-benzofuran derivatives containing 3-(4-fluorophenylsulfonyl) (Choi et al., 2010) and 3-(4-methylphenylsulfonyl) (Choi et al., 2012) substituents, 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 0.006 (2) Å from the least-squares plane defined by the nine constituent atoms. In the 3-fluorophenyl ring, the F atom is disordered over two positions with site-occupancy factors, from refinement of 0.887 (3) (part A) and 0.113 (3) (part B). The dihedral angle between the 3-fluorophenyl ring and the mean plane of the benzofuran ring is 79.51 (6)°. In the crystal structure (Fig. 2), molecules are connected by weak intermolecular C–H···F and C–H···O hydrogen bonds (Table 1). The crystal packing (Fig. 3) also exhibits slipped π–π interactions between the benzene and furan rings of neighbouring molecules, with Cg1···Cg2iii and Cg1···Cg2iv distances of 3.563 (3) Å & 3.820 (3) Å, and interplanar distances of 3.545 (3) Å & 3.491 (3) Å resulting in slippages of 0.358 (3) Å & 1.551 (3) Å (Cg1 and Cg2 are the centroids of the C2-C7 benzene ring and the C1/C2/C7/O1/C8 furan ring, respectively).

For background information and the crystal structures of related compounds, see: Choi et al. (2010, 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 (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 displacement ellipsoids drawn at the 50% probability level. H atoms are presented as small spheres of arbitrary radius. The F atom of the 3-fluorophenyl ring is disordered over two positions with refined site occupancy factors, of 0.887 (3) (part A) and 0.113 (3) (part B).
[Figure 2] Fig. 2. A view of the C–H···F and C–H···O interactions (dotted lines) in the crystal structure of the title compound. H atoms not participating in hydrogen-bonding were omitted for clarity. [Symmetry codes: (i) x - 1/2, - y + 1/2, z - 1/2; (ii) - x + 1/2, y - 1/2, - z + 3/2; (v) x + 1/2, - y + 1/2, z + 1/2; (vi) - x + 1/2, y + 1/2, - z + 3/2.]
[Figure 3] Fig. 3. A view of the π–π interactions (dotted lines) in the crystal structure of the title compound. All H atoms were omitted for clarity. [Symmetry codes: (iii) - x, - y + 1, - z + 1; (iv) - x + 1, - y + 1, - z + 1]
5-Fluoro-3-(3-fluorophenylsulfonyl)-2-methyl-1-benzofuran top
Crystal data top
C15H10F2O3SF(000) = 632
Mr = 308.29Dx = 1.558 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 3933 reflections
a = 7.2772 (2) Åθ = 2.2–28.2°
b = 11.0972 (3) ŵ = 0.28 mm−1
c = 16.5625 (5) ÅT = 296 K
β = 100.698 (2)°Block, colourless
V = 1314.28 (6) Å30.30 × 0.22 × 0.20 mm
Z = 4
Data collection top
Bruker SMART APEXII CCD
diffractometer		3275 independent reflections
Radiation source: rotating anode2732 reflections with I > 2σ(I)
Graphite multilayer monochromatorRint = 0.032
Detector resolution: 10.0 pixels mm-1θmax = 28.3°, θmin = 2.2°
φ and ω scansh = −9→9
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		k = −14→14
Tmin = 0.663, Tmax = 0.746l = −22→22
12792 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037H-atom parameters constrained
wR(F2) = 0.104 w = 1/[σ2(Fo2) + (0.0548P)2 + 0.3108P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
3275 reflectionsΔρmax = 0.36 e Å−3
202 parametersΔρmin = −0.31 e Å−3
14 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0088 (14)
Crystal data top
C15H10F2O3SV = 1314.28 (6) Å3
Mr = 308.29Z = 4
Monoclinic, P21/nMo Kα radiation
a = 7.2772 (2) ŵ = 0.28 mm−1
b = 11.0972 (3) ÅT = 296 K
c = 16.5625 (5) Å0.30 × 0.22 × 0.20 mm
β = 100.698 (2)°
Data collection top
Bruker SMART APEXII CCD
diffractometer		3275 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		2732 reflections with I > 2σ(I)
Tmin = 0.663, Tmax = 0.746Rint = 0.032
12792 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.03714 restraints
wR(F2) = 0.104H-atom parameters constrained
S = 1.04Δρmax = 0.36 e Å−3
3275 reflectionsΔρmin = −0.31 e Å−3
202 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*/UeqOcc. (<1)
S10.21640 (5)0.63440 (3)0.70540 (2)0.03087 (13)
F10.25059 (17)0.17801 (10)0.54399 (7)0.0617 (3)
O10.25258 (16)0.65312 (11)0.47256 (7)0.0437 (3)
O20.13169 (15)0.52825 (10)0.73181 (7)0.0373 (3)
O30.13613 (15)0.75027 (10)0.71521 (7)0.0407 (3)
C10.2307 (2)0.61487 (14)0.60279 (9)0.0324 (3)
C20.24256 (19)0.49996 (14)0.56282 (9)0.0323 (3)
C30.2414 (2)0.37946 (15)0.58555 (10)0.0375 (4)
H30.23320.35590.63870.045*
C40.2532 (2)0.29710 (17)0.52459 (11)0.0437 (4)
C50.2648 (2)0.32726 (19)0.44430 (11)0.0491 (5)
H50.27150.26710.40590.059*
C60.2664 (2)0.44598 (18)0.42199 (10)0.0456 (4)
H60.27450.46880.36870.055*
C70.2553 (2)0.53018 (16)0.48228 (9)0.0369 (4)
C80.2376 (2)0.70287 (16)0.54652 (10)0.0391 (4)
C90.2333 (3)0.83607 (17)0.54796 (12)0.0547 (5)
H9A0.22650.86320.60240.082*
H9B0.12590.86440.51010.082*
H9C0.34490.86710.53240.082*
C100.4518 (2)0.63802 (13)0.75603 (9)0.0298 (3)
C110.5530 (2)0.74450 (14)0.75670 (10)0.0375 (3)
H110.49570.81430.73320.045*
C120.7390 (2)0.74468 (16)0.79277 (11)0.0420 (4)0.887 (3)
H120.80830.81500.79250.050*0.887 (3)
C12'0.7390 (2)0.74468 (16)0.79277 (11)0.0420 (4)0.11
F2'0.8472 (11)0.8379 (6)0.8099 (5)0.042 (3)0.113 (3)
C130.8244 (2)0.64277 (16)0.82925 (10)0.0409 (4)
H130.95040.64340.85350.049*
C140.7198 (2)0.54100 (15)0.82885 (10)0.0402 (4)0.887 (3)
F20.80371 (19)0.44337 (11)0.86633 (8)0.0619 (4)0.887 (3)
C14'0.7198 (2)0.54100 (15)0.82885 (10)0.0402 (4)0.11
H14'0.77700.47260.85460.048*0.113 (3)
C150.5338 (2)0.53388 (14)0.79236 (9)0.0354 (3)
H150.46660.46260.79210.042*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0314 (2)0.0312 (2)0.0326 (2)0.00158 (14)0.01275 (15)−0.00048 (14)
F10.0746 (8)0.0435 (6)0.0622 (7)0.0073 (6)−0.0001 (6)−0.0119 (5)
O10.0432 (7)0.0576 (8)0.0303 (6)−0.0037 (5)0.0070 (5)0.0065 (5)
O20.0380 (6)0.0387 (6)0.0384 (6)−0.0052 (5)0.0158 (5)−0.0007 (5)
O30.0392 (6)0.0379 (6)0.0478 (7)0.0076 (5)0.0157 (5)−0.0022 (5)
C10.0281 (7)0.0384 (8)0.0318 (7)0.0015 (6)0.0084 (6)0.0008 (6)
C20.0227 (7)0.0446 (9)0.0293 (7)0.0015 (6)0.0044 (5)−0.0022 (6)
C30.0337 (8)0.0431 (9)0.0347 (8)0.0026 (6)0.0040 (6)−0.0033 (6)
C40.0373 (9)0.0446 (10)0.0459 (9)0.0041 (7)−0.0007 (7)−0.0090 (7)
C50.0390 (9)0.0659 (13)0.0404 (9)0.0022 (8)0.0023 (7)−0.0205 (9)
C60.0346 (8)0.0720 (13)0.0296 (8)−0.0023 (8)0.0046 (6)−0.0066 (8)
C70.0265 (7)0.0530 (10)0.0306 (7)−0.0012 (6)0.0044 (6)0.0004 (7)
C80.0342 (8)0.0475 (10)0.0360 (8)0.0008 (7)0.0072 (6)0.0050 (7)
C90.0671 (13)0.0459 (11)0.0512 (11)−0.0017 (9)0.0116 (9)0.0113 (8)
C100.0329 (7)0.0301 (7)0.0287 (7)0.0007 (6)0.0117 (6)−0.0034 (5)
C110.0417 (8)0.0307 (8)0.0419 (8)−0.0004 (6)0.0126 (7)0.0003 (6)
C120.0406 (9)0.0416 (9)0.0457 (9)−0.0081 (7)0.0131 (7)−0.0085 (7)
C12'0.0406 (9)0.0416 (9)0.0457 (9)−0.0081 (7)0.0131 (7)−0.0085 (7)
F2'0.038 (4)0.041 (5)0.048 (5)−0.014 (3)0.013 (3)−0.005 (3)
C130.0344 (8)0.0540 (10)0.0345 (8)0.0003 (7)0.0072 (6)−0.0090 (7)
C140.0445 (9)0.0409 (9)0.0348 (8)0.0089 (7)0.0065 (7)0.0014 (7)
F20.0601 (8)0.0469 (8)0.0715 (9)0.0124 (6)−0.0070 (7)0.0121 (6)
C14'0.0445 (9)0.0409 (9)0.0348 (8)0.0089 (7)0.0065 (7)0.0014 (7)
C150.0416 (8)0.0303 (8)0.0355 (8)−0.0009 (6)0.0103 (6)−0.0006 (6)
Geometric parameters (Å, º) top
S1—O31.4339 (11)C6—H60.9300
S1—O21.4349 (11)C8—C91.479 (2)
S1—C11.7354 (15)C9—H9A0.9600
S1—C101.7627 (16)C9—H9B0.9600
F1—C41.361 (2)C9—H9C0.9600
O1—C81.366 (2)C10—C151.386 (2)
O1—C71.374 (2)C10—C111.391 (2)
C1—C81.357 (2)C11—C121.374 (2)
C1—C21.447 (2)C11—H110.9300
C2—C31.390 (2)C12—C131.375 (2)
C2—C71.395 (2)C12—H120.9300
C3—C41.376 (2)C13—C141.361 (2)
C3—H30.9300C13—H130.9300
C4—C51.389 (3)C14—F21.3383 (19)
C5—C61.369 (3)C14—C151.378 (2)
C5—H50.9300C15—H150.9300
C6—C71.381 (2)
O3—S1—O2119.64 (7)C1—C8—O1110.14 (15)
O3—S1—C1108.82 (7)C1—C8—C9134.79 (16)
O2—S1—C1107.65 (7)O1—C8—C9115.07 (15)
O3—S1—C10107.83 (7)C8—C9—H9A109.5
O2—S1—C10107.96 (7)C8—C9—H9B109.5
C1—S1—C10103.84 (7)H9A—C9—H9B109.5
C8—O1—C7107.34 (12)C8—C9—H9C109.5
C8—C1—C2107.87 (13)H9A—C9—H9C109.5
C8—C1—S1126.82 (13)H9B—C9—H9C109.5
C2—C1—S1125.29 (11)C15—C10—C11121.37 (15)
C3—C2—C7119.67 (15)C15—C10—S1119.32 (12)
C3—C2—C1136.08 (14)C11—C10—S1119.29 (12)
C7—C2—C1104.24 (14)C12—C11—C10118.79 (15)
C4—C3—C2115.85 (15)C12—C11—H11120.6
C4—C3—H3122.1C10—C11—H11120.6
C2—C3—H3122.1C11—C12—C13121.22 (16)
F1—C4—C3117.79 (16)C11—C12—H12119.4
F1—C4—C5117.77 (16)C13—C12—H12119.4
C3—C4—C5124.43 (18)C14—C13—C12118.25 (16)
C6—C5—C4119.70 (16)C14—C13—H13120.9
C6—C5—H5120.2C12—C13—H13120.9
C4—C5—H5120.2F2—C14—C13117.58 (16)
C5—C6—C7116.84 (16)F2—C14—C15118.89 (16)
C5—C6—H6121.6C13—C14—C15123.53 (15)
C7—C6—H6121.6C14—C15—C10116.82 (15)
O1—C7—C6126.08 (15)C14—C15—H15121.6
O1—C7—C2110.41 (14)C10—C15—H15121.6
C6—C7—C2123.51 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5—H5···F2i0.932.453.302 (2)153
C15—H15···O3ii0.932.473.3754 (19)165
Symmetry codes: (i) x−1/2, −y+1/2, z−1/2; (ii) −x+1/2, y−1/2, −z+3/2.

Experimental details

Crystal data
Chemical formulaC15H10F2O3S
Mr308.29
Crystal system, space groupMonoclinic, P21/n
Temperature (K)296
a, b, c (Å)7.2772 (2), 11.0972 (3), 16.5625 (5)
β (°) 100.698 (2)
V (Å3)1314.28 (6)
Z4
Radiation typeMo Kα
µ (mm−1)0.28
Crystal size (mm)0.30 × 0.22 × 0.20
Data collection
DiffractometerBruker SMART APEXII CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.663, 0.746
No. of measured, independent and
observed [I > 2σ(I)] reflections		12792, 3275, 2732
Rint0.032
(sin θ/λ)max (Å−1)0.667
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.037, 0.104, 1.04
No. of reflections3275
No. of parameters202
No. of restraints14
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.36, −0.31

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···F2i0.932.453.302 (2)152.6
C15—H15···O3ii0.932.473.3754 (19)165.2
Symmetry codes: (i) x−1/2, −y+1/2, z−1/2; (ii) −x+1/2, y−1/2, −z+3/2.
 

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, o455.  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, o1909.  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 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.

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ISSN: 2056-9890
Volume 68| Part 8| August 2012| Page o2477
https://doi.org/10.1107/S1600536812031972
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