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

Choi, H.D.; Seo, P.J.; Son, B.W.; Lee, U.

doi:10.1107/S1600536811018654

organic compounds

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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Page o1468

doi:10.1107/S1600536811018654

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

Hong Dae Choi,^a Pil Ja Seo,^a Byeng Wha Son ^b and Uk Lee ^b ^*

^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 7 April 2011; accepted 17 May 2011; online 20 May 2011)

In the title compound, C₁₇H₁₅FO₂S, the 3-fluorophenyl ring makes a dihedral angle of 86.89 (4)° with the mean plane of the benzofuran fragment. In the crystal, molecules are linked by weak intermolecular C—H⋯O hydrogen bonds. The crystal structure also exhibits a slipped π–π interaction between the furan rings of neighbouring molecules [centroid–centroid distance = 3.719 (2) Å, interplanar distance = 3.475 (2) Å and slippage = 1.325 Å].

Related literature

For the biological 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 3-(4-fluorophenylsulfinyl)-2,5-dimethyl-1-benzofuran derivatives, see: Choi et al. (2010a ,b ).

Experimental

Crystal data

C₁₇H₁₅FO₂S
M_r = 302.35
Triclinic, $[P \overline 1]$
a = 6.2942 (2) Å
b = 11.1162 (4) Å
c = 11.8021 (6) Å
α = 110.701 (3)°
β = 100.176 (3)°
γ = 103.621 (2)°
V = 719.39 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 296 K
0.29 × 0.25 × 0.21 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.935, T_max = 0.951
12696 measured reflections
3301 independent reflections
2760 reflections with I > 2σ(I)
R_int = 0.122

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.133
S = 1.07
3301 reflections
193 parameters
H-atom parameters constrained
Δρ_max = 0.52 e Å⁻³
Δρ_min = −0.44 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O2ⁱ	0.93	2.51	3.227 (2)	134
Symmetry code: (i) -x+2, -y+1, -z+2.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811018654/ez2242sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811018654/ez2242Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811018654/ez2242Isup3.cml

checkCIF report

Comment top

Many compounds containing a benzofuran ring system exhibit interesting 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 compounds occur in a wide range of natural products (Akgul & Anil, 2003; Soekamto et al., 2003). As a part of our study of the substituent effect on the solid state structures of 3-(4-fluorophenylsulfinyl)-2,5-dimethyl-1-benzofuran analogues (Choi et al., 2010a,b), we report the crystal structure of the title compound.

In the title compound (Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.007 (1) Å from the least-squares plane defined by the nine constituent atoms. The 3-fluorophenyl ring makes a dihedral angle of 86.89 (4)° with the mean plane of the benzofuran fragment. The crystal packing (Fig. 2) is stabilized by weak intermolecular C—H···O hydrogen bonds between a 3-fluorophenyl H atom and the O atom of the sulfinyl group (Table 1; C13—H13···O2ⁱ). The crystal packing (Fig. 2) is further stabilized by a weak slipped π–π interaction between the furan rings of neighbouring molecules, with a Cg···Cgⁱⁱ distance of 3.719 (2) Å and an interplanar distance of 3.475 (2) Å resulting in a slippage of 1.325 Å (Cg is the centroid of the C1/C2/C7/O1/C8 furan ring).

Related literature top

For the biological 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 3-(4-fluorophenylsulfinyl)-2,5-dimethyl-1-benzofuran derivatives, see: Choi et al. (2010a,b).

Experimental top

77% 3-chloroperoxybenzoic acid (291 mg, 1.3 mmol) was added in small portions to a stirred solution of 3-(3-fluorophenylsulfanyl)-2,5,7-trimethyl-1-benzofuran (342 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 75%, m.p. 434–435 K; R_f = 0.72 (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.

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

	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.
	Fig. 2. A view of the C—H···O and π–π interactions (dotted lines) in the crystal structure of the title compound. [Symmetry codes: (i) - x + 2, - y + 1, - z + 2 ; (ii) - x + , - y + 1, - z + 1.]

3-(3-Fluorophenylsulfinyl)-2,5,7-trimethyl-1-benzofuran top

Crystal data top

C₁₇H₁₅FO₂S	Z = 2
M_r = 302.35	F(000) = 316
Triclinic, P1	D_x = 1.396 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.2942 (2) Å	Cell parameters from 5769 reflections
b = 11.1162 (4) Å	θ = 2.2–27.5°
c = 11.8021 (6) Å	µ = 0.24 mm⁻¹
α = 110.701 (3)°	T = 296 K
β = 100.176 (3)°	Block, colourless
γ = 103.621 (2)°	0.29 × 0.25 × 0.21 mm
V = 719.39 (5) Å³

Data collection top

Bruker SMART APEXII CCD diffractometer	3301 independent reflections
Radiation source: rotating anode	2760 reflections with I > 2σ(I)
Graphite multilayer monochromator	R_int = 0.122
Detector resolution: 10.0 pixels mm^-1	θ_max = 27.5°, θ_min = 1.9°
ϕ and ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −14→14
T_min = 0.935, T_max = 0.951	l = −15→15
12696 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.047	Hydrogen site location: difference Fourier map
wR(F²) = 0.133	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0679P)² + 0.086P] where P = (F_o² + 2F_c²)/3
3301 reflections	(Δ/σ)_max < 0.001
193 parameters	Δρ_max = 0.52 e Å⁻³
0 restraints	Δρ_min = −0.44 e Å⁻³

Crystal data top

C₁₇H₁₅FO₂S	γ = 103.621 (2)°
M_r = 302.35	V = 719.39 (5) Å³
Triclinic, P1	Z = 2
a = 6.2942 (2) Å	Mo Kα radiation
b = 11.1162 (4) Å	µ = 0.24 mm⁻¹
c = 11.8021 (6) Å	T = 296 K
α = 110.701 (3)°	0.29 × 0.25 × 0.21 mm
β = 100.176 (3)°

Data collection top

Bruker SMART APEXII CCD diffractometer	3301 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2760 reflections with I > 2σ(I)
T_min = 0.935, T_max = 0.951	R_int = 0.122
12696 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.133	H-atom parameters constrained
S = 1.07	Δρ_max = 0.52 e Å⁻³
3301 reflections	Δρ_min = −0.44 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

	x	y	z	U_iso*/U_eq
S1	0.61779 (7)	0.50213 (4)	0.83763 (4)	0.02605 (15)
O1	0.2342 (2)	0.38830 (12)	0.49387 (10)	0.0275 (3)
O2	0.8652 (2)	0.52089 (14)	0.85568 (12)	0.0361 (3)
F1	0.7099 (2)	0.14993 (13)	1.00630 (12)	0.0517 (4)
C1	0.4798 (3)	0.42715 (17)	0.67501 (15)	0.0249 (3)
C2	0.5132 (3)	0.31895 (16)	0.57616 (15)	0.0250 (3)
C3	0.6547 (3)	0.23900 (18)	0.56868 (17)	0.0303 (4)
H3	0.7618	0.2516	0.6406	0.036*
C4	0.6325 (3)	0.14076 (18)	0.45232 (18)	0.0342 (4)
C5	0.4696 (3)	0.12330 (18)	0.34451 (18)	0.0350 (4)
H5	0.4573	0.0561	0.2670	0.042*
C6	0.3262 (3)	0.20148 (18)	0.34811 (16)	0.0307 (4)
C7	0.3566 (3)	0.29841 (16)	0.46668 (15)	0.0256 (4)
C8	0.3133 (3)	0.46537 (17)	0.62103 (15)	0.0253 (3)
C9	0.7843 (4)	0.0524 (2)	0.4405 (2)	0.0470 (5)
H9A	0.9238	0.0970	0.4290	0.070*
H9B	0.7075	−0.0332	0.3691	0.070*
H9C	0.8177	0.0373	0.5160	0.070*
C10	0.1525 (4)	0.1847 (2)	0.23408 (17)	0.0417 (5)
H10A	0.0034	0.1632	0.2459	0.063*
H10B	0.1568	0.1125	0.1608	0.063*
H10C	0.1863	0.2678	0.2226	0.063*
C11	0.2019 (3)	0.56740 (18)	0.67277 (17)	0.0324 (4)
H11A	0.0490	0.5220	0.6687	0.049*
H11B	0.1982	0.6205	0.6241	0.049*
H11C	0.2863	0.6259	0.7591	0.049*
C12	0.5032 (3)	0.35709 (16)	0.86983 (14)	0.0243 (3)
C13	0.6565 (3)	0.30906 (17)	0.92600 (15)	0.0280 (4)
H13	0.8132	0.3478	0.9441	0.034*
C14	0.5646 (3)	0.20107 (18)	0.95355 (17)	0.0326 (4)
C15	0.3363 (3)	0.14339 (18)	0.93105 (17)	0.0352 (4)
H15	0.2814	0.0706	0.9513	0.042*
C16	0.1877 (3)	0.19579 (19)	0.87727 (18)	0.0352 (4)
H16	0.0313	0.1583	0.8618	0.042*
C17	0.2699 (3)	0.30294 (18)	0.84667 (17)	0.0309 (4)
H17	0.1703	0.3384	0.8110	0.037*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0285 (3)	0.0248 (2)	0.0201 (2)	0.00624 (17)	0.00117 (16)	0.00820 (17)
O1	0.0280 (6)	0.0311 (6)	0.0233 (6)	0.0126 (5)	0.0020 (5)	0.0117 (5)
O2	0.0248 (6)	0.0437 (7)	0.0335 (7)	0.0014 (5)	−0.0012 (5)	0.0196 (6)
F1	0.0560 (8)	0.0466 (7)	0.0606 (8)	0.0225 (6)	0.0038 (6)	0.0334 (7)
C1	0.0251 (8)	0.0269 (8)	0.0228 (8)	0.0100 (6)	0.0033 (6)	0.0111 (7)
C2	0.0256 (8)	0.0249 (8)	0.0247 (8)	0.0080 (7)	0.0053 (6)	0.0115 (7)
C3	0.0283 (9)	0.0320 (9)	0.0349 (9)	0.0141 (7)	0.0078 (7)	0.0163 (8)
C4	0.0365 (10)	0.0290 (9)	0.0430 (11)	0.0148 (8)	0.0173 (8)	0.0159 (8)
C5	0.0454 (11)	0.0257 (8)	0.0300 (9)	0.0093 (8)	0.0147 (8)	0.0067 (8)
C6	0.0352 (9)	0.0274 (8)	0.0255 (8)	0.0058 (7)	0.0078 (7)	0.0098 (7)
C7	0.0267 (8)	0.0248 (8)	0.0250 (8)	0.0091 (7)	0.0059 (7)	0.0104 (7)
C8	0.0267 (8)	0.0264 (8)	0.0222 (8)	0.0084 (7)	0.0040 (6)	0.0110 (7)
C9	0.0534 (13)	0.0413 (11)	0.0591 (13)	0.0285 (10)	0.0272 (11)	0.0216 (11)
C10	0.0533 (12)	0.0370 (10)	0.0235 (9)	0.0065 (9)	0.0003 (8)	0.0101 (8)
C11	0.0341 (10)	0.0335 (9)	0.0336 (9)	0.0173 (8)	0.0086 (8)	0.0148 (8)
C12	0.0290 (8)	0.0238 (8)	0.0164 (7)	0.0082 (6)	0.0034 (6)	0.0058 (6)
C13	0.0275 (8)	0.0291 (8)	0.0241 (8)	0.0100 (7)	0.0031 (7)	0.0088 (7)
C14	0.0439 (10)	0.0287 (8)	0.0261 (8)	0.0176 (8)	0.0051 (8)	0.0109 (7)
C15	0.0465 (11)	0.0263 (9)	0.0292 (9)	0.0071 (8)	0.0104 (8)	0.0104 (7)
C16	0.0306 (9)	0.0335 (9)	0.0360 (10)	0.0046 (8)	0.0098 (8)	0.0116 (8)
C17	0.0270 (8)	0.0339 (9)	0.0292 (9)	0.0107 (7)	0.0038 (7)	0.0116 (8)

Geometric parameters (Å, º) top

S1—O2	1.4876 (13)	C9—H9A	0.9600
S1—C1	1.7527 (16)	C9—H9B	0.9600
S1—C12	1.8017 (17)	C9—H9C	0.9600
O1—C8	1.3639 (19)	C10—H10A	0.9600
O1—C7	1.3851 (19)	C10—H10B	0.9600
F1—C14	1.357 (2)	C10—H10C	0.9600
C1—C8	1.360 (2)	C11—H11A	0.9600
C1—C2	1.437 (2)	C11—H11B	0.9600
C2—C7	1.389 (2)	C11—H11C	0.9600
C2—C3	1.391 (2)	C12—C17	1.386 (2)
C3—C4	1.378 (3)	C12—C13	1.386 (2)
C3—H3	0.9300	C13—C14	1.377 (3)
C4—C5	1.407 (3)	C13—H13	0.9300
C4—C9	1.513 (2)	C14—C15	1.363 (3)
C5—C6	1.389 (3)	C15—C16	1.388 (3)
C5—H5	0.9300	C15—H15	0.9300
C6—C7	1.378 (2)	C16—C17	1.377 (3)
C6—C10	1.499 (2)	C16—H16	0.9300
C8—C11	1.479 (2)	C17—H17	0.9300

O2—S1—C1	108.38 (8)	H9A—C9—H9C	109.5
O2—S1—C12	105.93 (7)	H9B—C9—H9C	109.5
C1—S1—C12	97.25 (7)	C6—C10—H10A	109.5
C8—O1—C7	106.64 (12)	C6—C10—H10B	109.5
C8—C1—C2	107.69 (14)	H10A—C10—H10B	109.5
C8—C1—S1	123.27 (13)	C6—C10—H10C	109.5
C2—C1—S1	129.04 (12)	H10A—C10—H10C	109.5
C7—C2—C3	119.25 (15)	H10B—C10—H10C	109.5
C7—C2—C1	104.76 (13)	C8—C11—H11A	109.5
C3—C2—C1	135.99 (15)	C8—C11—H11B	109.5
C4—C3—C2	118.52 (16)	H11A—C11—H11B	109.5
C4—C3—H3	120.7	C8—C11—H11C	109.5
C2—C3—H3	120.7	H11A—C11—H11C	109.5
C3—C4—C5	119.93 (16)	H11B—C11—H11C	109.5
C3—C4—C9	119.97 (17)	C17—C12—C13	121.95 (16)
C5—C4—C9	120.09 (18)	C17—C12—S1	120.18 (12)
C6—C5—C4	123.21 (17)	C13—C12—S1	117.72 (13)
C6—C5—H5	118.4	C14—C13—C12	116.56 (16)
C4—C5—H5	118.4	C14—C13—H13	121.7
C7—C6—C5	114.34 (16)	C12—C13—H13	121.7
C7—C6—C10	121.75 (17)	F1—C14—C15	118.44 (17)
C5—C6—C10	123.91 (17)	F1—C14—C13	118.02 (17)
C6—C7—O1	124.90 (15)	C15—C14—C13	123.54 (16)
C6—C7—C2	124.74 (15)	C14—C15—C16	118.45 (17)
O1—C7—C2	110.36 (14)	C14—C15—H15	120.8
C1—C8—O1	110.54 (14)	C16—C15—H15	120.8
C1—C8—C11	133.15 (16)	C17—C16—C15	120.52 (17)
O1—C8—C11	116.28 (13)	C17—C16—H16	119.7
C4—C9—H9A	109.5	C15—C16—H16	119.7
C4—C9—H9B	109.5	C16—C17—C12	118.94 (16)
H9A—C9—H9B	109.5	C16—C17—H17	120.5
C4—C9—H9C	109.5	C12—C17—H17	120.5

O2—S1—C1—C8	−138.58 (15)	C1—C2—C7—C6	−178.81 (16)
C12—S1—C1—C8	111.91 (16)	C3—C2—C7—O1	−179.52 (15)
O2—S1—C1—C2	41.89 (18)	C1—C2—C7—O1	0.63 (19)
C12—S1—C1—C2	−67.61 (17)	C2—C1—C8—O1	0.7 (2)
C8—C1—C2—C7	−0.79 (19)	S1—C1—C8—O1	−178.92 (12)
S1—C1—C2—C7	178.79 (14)	C2—C1—C8—C11	178.47 (19)
C8—C1—C2—C3	179.4 (2)	S1—C1—C8—C11	−1.1 (3)
S1—C1—C2—C3	−1.0 (3)	C7—O1—C8—C1	−0.30 (19)
C7—C2—C3—C4	−0.7 (3)	C7—O1—C8—C11	−178.49 (15)
C1—C2—C3—C4	179.12 (19)	O2—S1—C12—C17	−172.33 (13)
C2—C3—C4—C5	0.1 (3)	C1—S1—C12—C17	−60.80 (15)
C2—C3—C4—C9	179.70 (17)	O2—S1—C12—C13	12.06 (14)
C3—C4—C5—C6	0.2 (3)	C1—S1—C12—C13	123.59 (13)
C9—C4—C5—C6	−179.39 (19)	C17—C12—C13—C14	2.3 (2)
C4—C5—C6—C7	0.1 (3)	S1—C12—C13—C14	177.84 (12)
C4—C5—C6—C10	179.67 (18)	C12—C13—C14—F1	178.73 (15)
C5—C6—C7—O1	179.93 (16)	C12—C13—C14—C15	−1.5 (3)
C10—C6—C7—O1	0.3 (3)	F1—C14—C15—C16	179.91 (16)
C5—C6—C7—C2	−0.7 (3)	C13—C14—C15—C16	0.1 (3)
C10—C6—C7—C2	179.67 (17)	C14—C15—C16—C17	0.5 (3)
C8—O1—C7—C6	179.21 (16)	C15—C16—C17—C12	0.3 (3)
C8—O1—C7—C2	−0.23 (19)	C13—C12—C17—C16	−1.8 (3)
C3—C2—C7—C6	1.0 (3)	S1—C12—C17—C16	−177.22 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O2ⁱ	0.93	2.51	3.227 (2)	134

Symmetry code: (i) −x+2, −y+1, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₅FO₂S
M_r	302.35
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	6.2942 (2), 11.1162 (4), 11.8021 (6)
α, β, γ (°)	110.701 (3), 100.176 (3), 103.621 (2)
V (Å³)	719.39 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.29 × 0.25 × 0.21

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.935, 0.951
No. of measured, independent and observed [I > 2σ(I)] reflections	12696, 3301, 2760
R_int	0.122
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.133, 1.07
No. of reflections	3301
No. of parameters	193
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.52, −0.44

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···A	D—H	H···A	D···A	D—H···A
C13—H13···O2ⁱ	0.93	2.51	3.227 (2)	134

Symmetry code: (i) −x+2, −y+1, −z+2.

References

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Volume 67| Part 6| June 2011| Page o1468

doi:10.1107/S1600536811018654

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