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ISSN: 2056-9890

5-Bromo-3-(4-fluoro­phenyl­sulfin­yl)-2,4,6-tri­methyl-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 13 January 2011; accepted 15 January 2011; online 22 January 2011)

In the title mol­ecule, C17H14BrFO2S, the 4-fluoro­phenyl ring makes a dihedral angle of 75.92 (5)° with the mean plane of the benzofuran fragment. In the crystal, mol­ecules are linked by weak inter­molecular C—H⋯O hydrogen bonds and aromatic ππ inter­actions between the benzene and the furan rings of neighbouring mol­ecules [centroid–centroid distance = 3.556 (1) Å].

Related literature

For the pharmacological activity of benzofuran compounds, see: Aslam et al. (2006[Aslam, S. N., Stevenson, P. C., Phythian, S. J., Veitch, N. C. & Hall, D. R. (2006). Tetrahedron, 62, 4214-4226.]); 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 our previous structural studies of related 5-bromo-3-(4-fluoro­phenyl­sulfin­yl)-2-methyl-1-benzofuran derivatives, see: Choi et al. (2010[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010). Acta Cryst. E66, o1297.], 2011[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2011). Acta Cryst. E67, o351.]).

[Scheme 1]

Experimental

Crystal data
  • C17H14BrFO2S

  • Mr = 381.25

  • Triclinic, [P \overline 1]

  • a = 7.6121 (3) Å

  • b = 8.3551 (3) Å

  • c = 13.0681 (4) Å

  • α = 71.551 (2)°

  • β = 84.206 (2)°

  • γ = 74.850 (2)°

  • V = 760.86 (5) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 2.85 mm−1

  • T = 173 K

  • 0.29 × 0.28 × 0.18 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 = 0.621, Tmax = 0.746

  • 13138 measured reflections

  • 3491 independent reflections

  • 3041 reflections with I > 2σ(I)

  • Rint = 0.020

Refinement
  • R[F2 > 2σ(F2)] = 0.026

  • wR(F2) = 0.070

  • S = 1.03

  • 3491 reflections

  • 202 parameters

  • H-atom parameters constrained

  • Δρmax = 0.37 e Å−3

  • Δρmin = −0.36 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C14—H14⋯O2i 0.95 2.35 3.232 (2) 154
Symmetry code: (i) x-1, y, 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


Comment top

Many compounds containing a benzofuran ring show interesting potent pharmacological properties, such as antifungal, antitumor and antiviral, and antimicrobial activities (Aslam et al., 2006; Galal et al., 2009; Khan et al., 2005). These compounds occur in a wide range of natural products (Akgul & Anil, 2003; Soekamto et al., 2003). As a part of our ongoing study of the substituent effect on the solid state structures of 5-bromo-3-(4-fluorophenylsulfinyl)-2-methyl-1-benzofuran analogues (Choi et al., 2010; 2011), 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 0.004 (1)Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle formed by the mean plane of the benzofuran fragment and the 4-fluorophenyl ring is 75.92 (5)°.

In the crystal the molecular packing (Fig. 2) is stabilized by weak intermolecular C—H···O hydrogen bonds between the 4-fluorophenyl H-atom and the oxygen of the SO unit (Table 1; C14–H14···O2i). The crystal packing (Fig. 2) is further stabilized by aromatic ππ interactions between the benzene and furan rings of the adjacent molecules. The Cg1···Cg2ii distance of 3.556 (1)Å (Cg1 and Cg2 are the centroids of the C2-C7 benzene ring and the C1/C2/C7/O1/C8 furan ring, respectively; symmetry code: (ii) = - x + 2, - y + 1, - z + 1).

Related literature top

For the pharmacological activity of benzofuran compounds, see: Aslam et al. (2006); Galal et al. (2009); Khan et al. (2005). For natural products with benzofuran rings, see: Akgul & Anil (2003); Soekamto et al. (2003). For our previous structural studies of related 5-bromo-3-(4-fluorophenylsulfinyl)-2-methyl-1-benzofuran derivatives, see: Choi et al. (2010, 2011).

Experimental top

77% 3-chloroperoxybenzoic acid (224 mg, 1.0 mmol) was added in small portions to a stirred solution of 5-bromo-3-(4-fluorophenylsulfanyl)-2,4,6-trimethyl-1-benzofuran (329 mg, 0.9 mmol) in dichloromethane (30 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, 4:1 v/v) to afford the title compound as a colorless solid [yield 73%, m.p. 424–425 K; Rf = 0.54 (hexane–ethyl acetate, 4:1 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 the H-atoms were positioned geometrically and refined using a riding model: C–H = 0.95 Å for aryl and 0.98 Å for methyl H-atoms, with 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 and ππ interactions (dotted lines) in the crystal structure of the title compound [Cg1 and Cg2 are the centroids of the C2-C7 benzene ring and the C1/C2/C7/O1/C8 furan ring, respectively; Symmetry codes: (i) x - 1, y, z; (ii) - x + 2, - y + 1, - z + 1; (iii) - x + 1, - y + 1, - z + 1].
5-Bromo-3-(4-fluorophenylsulfinyl)-2,4,6-trimethyl-1-benzofuran top
Crystal data top
C17H14BrFO2SZ = 2
Mr = 381.25F(000) = 384
Triclinic, P1Dx = 1.664 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.6121 (3) ÅCell parameters from 6469 reflections
b = 8.3551 (3) Åθ = 2.7–27.4°
c = 13.0681 (4) ŵ = 2.85 mm1
α = 71.551 (2)°T = 173 K
β = 84.206 (2)°Block, colourless
γ = 74.850 (2)°0.29 × 0.28 × 0.18 mm
V = 760.86 (5) Å3
Data collection top
Bruker SMART APEXII CCD
diffractometer
3491 independent reflections
Radiation source: rotating anode3041 reflections with I > 2σ(I)
Graphite multilayer monochromatorRint = 0.020
Detector resolution: 10.0 pixels mm-1θmax = 27.6°, θmin = 1.6°
ϕ and ω scansh = 99
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
k = 1010
Tmin = 0.621, Tmax = 0.746l = 1616
13138 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)] = 0.026Hydrogen site location: difference Fourier map
wR(F2) = 0.070H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0383P)2 + 0.249P]
where P = (Fo2 + 2Fc2)/3
3491 reflections(Δ/σ)max = 0.001
202 parametersΔρmax = 0.37 e Å3
0 restraintsΔρmin = 0.36 e Å3
Crystal data top
C17H14BrFO2Sγ = 74.850 (2)°
Mr = 381.25V = 760.86 (5) Å3
Triclinic, P1Z = 2
a = 7.6121 (3) ÅMo Kα radiation
b = 8.3551 (3) ŵ = 2.85 mm1
c = 13.0681 (4) ÅT = 173 K
α = 71.551 (2)°0.29 × 0.28 × 0.18 mm
β = 84.206 (2)°
Data collection top
Bruker SMART APEXII CCD
diffractometer
3491 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
3041 reflections with I > 2σ(I)
Tmin = 0.621, Tmax = 0.746Rint = 0.020
13138 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0260 restraints
wR(F2) = 0.070H-atom parameters constrained
S = 1.03Δρmax = 0.37 e Å3
3491 reflectionsΔρmin = 0.36 e Å3
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*/Ueq
Br10.68278 (3)0.91822 (3)0.615760 (17)0.04054 (8)
S10.95005 (6)0.77098 (6)0.16447 (4)0.02943 (11)
F10.29820 (17)1.33971 (15)0.03005 (12)0.0499 (3)
O10.81454 (17)0.38324 (15)0.38631 (10)0.0286 (3)
O21.09273 (18)0.84985 (19)0.18473 (12)0.0412 (3)
C10.8798 (2)0.6334 (2)0.28464 (14)0.0245 (3)
C20.8185 (2)0.6538 (2)0.38953 (14)0.0231 (3)
C30.7943 (2)0.7847 (2)0.43920 (15)0.0255 (4)
C40.7266 (2)0.7438 (2)0.54461 (15)0.0273 (4)
C50.6871 (2)0.5839 (2)0.60321 (15)0.0290 (4)
C60.7165 (2)0.4558 (2)0.55291 (16)0.0299 (4)
H60.69360.34500.58950.036*
C70.7801 (2)0.4951 (2)0.44808 (15)0.0252 (4)
C80.8752 (2)0.4705 (2)0.28794 (15)0.0267 (4)
C90.8414 (3)0.9549 (2)0.38215 (17)0.0351 (4)
H9A0.72981.04490.35730.053*
H9B0.92180.94350.32000.053*
H9C0.90350.98750.43180.053*
C100.6144 (3)0.5493 (3)0.71775 (17)0.0402 (5)
H10A0.60730.42760.74650.060*
H10B0.49270.62560.71910.060*
H10C0.69590.57200.76210.060*
C110.9167 (3)0.3742 (3)0.20722 (17)0.0348 (4)
H11A0.97110.44210.14230.052*
H11B0.80410.35500.18840.052*
H11C1.00240.26180.23760.052*
C120.7454 (2)0.9425 (2)0.13416 (14)0.0257 (4)
C130.5734 (2)0.9108 (2)0.15511 (15)0.0289 (4)
H130.56020.79700.19320.035*
C140.4209 (3)1.0452 (2)0.12041 (15)0.0309 (4)
H140.30191.02610.13430.037*
C150.4475 (3)1.2070 (2)0.06525 (16)0.0334 (4)
C160.6159 (3)1.2419 (2)0.04298 (16)0.0352 (4)
H160.62821.35590.00440.042*
C170.7673 (3)1.1072 (2)0.07804 (15)0.0304 (4)
H170.88581.12750.06370.036*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.04469 (13)0.04331 (13)0.03878 (13)0.00562 (9)0.00095 (9)0.02358 (10)
S10.0305 (2)0.0312 (2)0.0273 (2)0.01179 (18)0.00611 (18)0.00835 (18)
F10.0479 (7)0.0343 (6)0.0595 (8)0.0004 (5)0.0100 (6)0.0080 (6)
O10.0337 (7)0.0233 (6)0.0299 (7)0.0091 (5)0.0026 (5)0.0073 (5)
O20.0314 (7)0.0458 (8)0.0478 (9)0.0209 (6)0.0053 (6)0.0088 (7)
C10.0236 (8)0.0255 (8)0.0251 (9)0.0081 (6)0.0015 (7)0.0065 (7)
C20.0202 (8)0.0248 (8)0.0249 (9)0.0072 (6)0.0015 (7)0.0068 (7)
C30.0239 (8)0.0250 (8)0.0288 (9)0.0073 (7)0.0038 (7)0.0076 (7)
C40.0247 (8)0.0307 (9)0.0285 (9)0.0038 (7)0.0036 (7)0.0132 (8)
C50.0228 (8)0.0370 (9)0.0251 (9)0.0063 (7)0.0024 (7)0.0065 (8)
C60.0293 (9)0.0281 (9)0.0293 (10)0.0095 (7)0.0033 (8)0.0019 (7)
C70.0235 (8)0.0235 (8)0.0285 (9)0.0052 (6)0.0054 (7)0.0067 (7)
C80.0254 (8)0.0273 (8)0.0281 (9)0.0064 (7)0.0037 (7)0.0083 (7)
C90.0463 (11)0.0296 (9)0.0351 (11)0.0175 (8)0.0016 (9)0.0115 (8)
C100.0366 (10)0.0530 (12)0.0297 (10)0.0125 (9)0.0059 (9)0.0113 (9)
C110.0390 (10)0.0322 (9)0.0369 (11)0.0072 (8)0.0012 (9)0.0168 (9)
C120.0334 (9)0.0271 (8)0.0203 (8)0.0123 (7)0.0025 (7)0.0092 (7)
C130.0365 (10)0.0282 (9)0.0242 (9)0.0147 (7)0.0005 (8)0.0057 (7)
C140.0337 (9)0.0361 (10)0.0272 (9)0.0138 (8)0.0008 (8)0.0118 (8)
C150.0414 (10)0.0300 (9)0.0292 (10)0.0052 (8)0.0047 (8)0.0108 (8)
C160.0509 (12)0.0249 (9)0.0321 (10)0.0155 (8)0.0015 (9)0.0065 (8)
C170.0394 (10)0.0314 (9)0.0261 (9)0.0189 (8)0.0031 (8)0.0095 (8)
Geometric parameters (Å, º) top
Br1—C41.9077 (18)C9—H9A0.9800
S1—O21.4922 (14)C9—H9B0.9800
S1—C11.7559 (18)C9—H9C0.9800
S1—C121.7990 (18)C10—H10A0.9800
F1—C151.363 (2)C10—H10B0.9800
O1—C81.364 (2)C10—H10C0.9800
O1—C71.379 (2)C11—H11A0.9800
C1—C81.357 (2)C11—H11B0.9800
C1—C21.450 (2)C11—H11C0.9800
C2—C71.395 (2)C12—C171.384 (2)
C2—C31.404 (2)C12—C131.387 (3)
C3—C41.390 (3)C13—C141.384 (3)
C3—C91.499 (2)C13—H130.9500
C4—C51.406 (3)C14—C151.373 (3)
C5—C61.386 (3)C14—H140.9500
C5—C101.508 (3)C15—C161.371 (3)
C6—C71.372 (3)C16—C171.381 (3)
C6—H60.9500C16—H160.9500
C8—C111.482 (3)C17—H170.9500
O2—S1—C1111.31 (9)H9A—C9—H9C109.5
O2—S1—C12106.48 (8)H9B—C9—H9C109.5
C1—S1—C1299.80 (8)C5—C10—H10A109.5
C8—O1—C7106.59 (13)C5—C10—H10B109.5
C8—C1—C2107.38 (15)H10A—C10—H10B109.5
C8—C1—S1118.89 (14)C5—C10—H10C109.5
C2—C1—S1133.73 (13)H10A—C10—H10C109.5
C7—C2—C3119.38 (16)H10B—C10—H10C109.5
C7—C2—C1104.21 (15)C8—C11—H11A109.5
C3—C2—C1136.40 (16)C8—C11—H11B109.5
C4—C3—C2115.25 (15)H11A—C11—H11B109.5
C4—C3—C9122.91 (16)C8—C11—H11C109.5
C2—C3—C9121.84 (16)H11A—C11—H11C109.5
C3—C4—C5125.19 (17)H11B—C11—H11C109.5
C3—C4—Br1117.61 (13)C17—C12—C13120.84 (17)
C5—C4—Br1117.20 (14)C17—C12—S1116.44 (14)
C6—C5—C4118.23 (17)C13—C12—S1122.38 (13)
C6—C5—C10119.74 (18)C14—C13—C12119.93 (16)
C4—C5—C10122.03 (18)C14—C13—H13120.0
C7—C6—C5117.35 (17)C12—C13—H13120.0
C7—C6—H6121.3C15—C14—C13117.72 (17)
C5—C6—H6121.3C15—C14—H14121.1
C6—C7—O1124.64 (16)C13—C14—H14121.1
C6—C7—C2124.57 (17)F1—C15—C16118.27 (17)
O1—C7—C2110.78 (15)F1—C15—C14118.11 (17)
C1—C8—O1111.03 (16)C16—C15—C14123.61 (18)
C1—C8—C11133.38 (18)C15—C16—C17118.30 (17)
O1—C8—C11115.56 (15)C15—C16—H16120.9
C3—C9—H9A109.5C17—C16—H16120.9
C3—C9—H9B109.5C16—C17—C12119.60 (17)
H9A—C9—H9B109.5C16—C17—H17120.2
C3—C9—H9C109.5C12—C17—H17120.2
O2—S1—C1—C8129.96 (14)C8—O1—C7—C20.00 (18)
C12—S1—C1—C8117.93 (14)C3—C2—C7—C60.9 (3)
O2—S1—C1—C250.88 (19)C1—C2—C7—C6179.68 (17)
C12—S1—C1—C261.23 (18)C3—C2—C7—O1179.17 (14)
C8—C1—C2—C70.43 (18)C1—C2—C7—O10.26 (18)
S1—C1—C2—C7178.79 (15)C2—C1—C8—O10.47 (19)
C8—C1—C2—C3178.85 (19)S1—C1—C8—O1178.89 (11)
S1—C1—C2—C31.9 (3)C2—C1—C8—C11178.42 (19)
C7—C2—C3—C42.0 (2)S1—C1—C8—C110.9 (3)
C1—C2—C3—C4178.83 (18)C7—O1—C8—C10.30 (19)
C7—C2—C3—C9177.13 (16)C7—O1—C8—C11178.65 (15)
C1—C2—C3—C92.1 (3)O2—S1—C12—C1734.56 (16)
C2—C3—C4—C51.8 (3)C1—S1—C12—C17150.39 (14)
C9—C3—C4—C5177.33 (17)O2—S1—C12—C13152.09 (15)
C2—C3—C4—Br1178.05 (12)C1—S1—C12—C1336.26 (17)
C9—C3—C4—Br12.9 (2)C17—C12—C13—C140.5 (3)
C3—C4—C5—C60.3 (3)S1—C12—C13—C14173.54 (14)
Br1—C4—C5—C6179.50 (13)C12—C13—C14—C150.3 (3)
C3—C4—C5—C10179.78 (18)C13—C14—C15—F1179.50 (17)
Br1—C4—C5—C100.4 (2)C13—C14—C15—C160.0 (3)
C4—C5—C6—C70.9 (3)F1—C15—C16—C17179.61 (17)
C10—C5—C6—C7179.00 (17)C14—C15—C16—C170.1 (3)
C5—C6—C7—O1179.30 (15)C15—C16—C17—C120.1 (3)
C5—C6—C7—C20.6 (3)C13—C12—C17—C160.4 (3)
C8—O1—C7—C6179.95 (17)S1—C12—C17—C16173.82 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C14—H14···O2i0.952.353.232 (2)154
Symmetry code: (i) x1, y, z.

Experimental details

Crystal data
Chemical formulaC17H14BrFO2S
Mr381.25
Crystal system, space groupTriclinic, P1
Temperature (K)173
a, b, c (Å)7.6121 (3), 8.3551 (3), 13.0681 (4)
α, β, γ (°)71.551 (2), 84.206 (2), 74.850 (2)
V3)760.86 (5)
Z2
Radiation typeMo Kα
µ (mm1)2.85
Crystal size (mm)0.29 × 0.28 × 0.18
Data collection
DiffractometerBruker SMART APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.621, 0.746
No. of measured, independent and
observed [I > 2σ(I)] reflections
13138, 3491, 3041
Rint0.020
(sin θ/λ)max1)0.651
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.026, 0.070, 1.03
No. of reflections3491
No. of parameters202
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.37, 0.36

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
C14—H14···O2i0.952.353.232 (2)154
Symmetry code: (i) x1, y, z.
 

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