3-Ethyl­sulfinyl-5-fluoro-2-(4-iodo­phen­yl)-1-benzofuran

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

doi:10.1107/S1600536810024736

organic compounds

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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1862

doi:10.1107/S1600536810024736

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3-Ethylsulfinyl-5-fluoro-2-(4-iodophenyl)-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 23 June 2010; accepted 24 June 2010; online 30 June 2010)

In the title compound, C₁₆H₁₂FIO₂S, the 4-iodophenyl ring is rotated slightly out of the benzofuran plane, as indicated by the dihedral angle of 11.41 (7)°. The crystal structure is stabilized by an intermolecular π–π interaction between the benzene and 4-iodophenyl rings [centroid–centroid distance = 3.757 (3) Å]. The crystal structure also exhibits a weak intermolecular C—H⋯O hydrogen bond and a short I⋯O [3.2575 (16) Å] contact.

Related literature

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 structures of related 3-ethylsulfinyl-2-(4-fluorophenyl)-5-halo-1-benzofuran derivatives, see: Choi et al. (2010a ,b ,c ). For a review of halogen bonding, see: Politzer et al. (2007 ).

Experimental

Crystal data

C₁₆H₁₂FIO₂S
M_r = 414.22
Monoclinic, P 2₁ /n
a = 7.5384 (4) Å
b = 9.4104 (5) Å
c = 20.3049 (9) Å
β = 96.298 (2)°
V = 1431.72 (12) Å³
Z = 4
Mo Kα radiation
μ = 2.39 mm⁻¹
T = 173 K
0.24 × 0.18 × 0.16 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.658, T_max = 0.680
12915 measured reflections
3265 independent reflections
3061 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.024
wR(F²) = 0.062
S = 1.13
3265 reflections
191 parameters
H-atom parameters constrained
Δρ_max = 0.53 e Å⁻³
Δρ_min = −0.78 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9B⋯O2ⁱ	0.97	2.59	3.337 (3)	134
Symmetry code: (i) -x, -y+2, -z+1.

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/S1600536810024736/is2566sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810024736/is2566Isup2.hkl

checkCIF report

Comment top

Compounds involving a benzofuran moiety show potent pharmacological properties such as antifungal (Aslam et al., 2006), antitumor and antiviral (Galal et al., 2009), antimicrobial (Khan et al., 2005) activities. These compounds occur widely in nature (Akgul & Anil, 2003; Soekamto et al., 2003). As a part of our ongoing studies of the substituent effect on the solid state structures of 3-ethylsulfinyl-2-(4-fluorophenyl)-5-halo-1-benzofuran analogues (Choi et al., 2010a,b,c), we report the crystal structure of the title compound (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 dihedral angle formed by the benzofuran plane and the 4-iodophenyl ring is 11.41 (7)°. The crystal packing (Fig. 2) is stabilized by aromatic π–π interactions between the benzene and the 4-iodophenyl rings of the neighbouring molecules, with a Cg1···Cg2ⁱⁱⁱ distance of 3.757 (3) Å (Cg1 and Cg2 are the centroids of the C2–C7 benzene ring and the C11–C16 4-iodophenyl ring, respectively). The molecular packing (Fig. 2) is further stabilized by a weak intermolecular C—H···O hydrogen bond between the methylene H atom of the ethyl group and the oxygen of the S═O unit, with a C9—H9B···O2ⁱ (Table 1). The crystal packing (Fig. 2) also exhibits an I···O halogen bonding between the iodine and the oxygen of the S═O unit [I···O2ⁱⁱ = 3.2575 (16) Å; C14—I···O2ⁱⁱ = 153.53 (6)°] (Politzer et al., 2007).

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 structures of related 3-ethylsulfinyl-2-(4-fluorophenyl)-5-halo-1-benzofuran derivatives, see: Choi et al. (2010a,b,c). For a review of halogen bonding, see: Politzer et al. (2007).

Experimental top

77% 3-Chloroperoxybenzoic acid (202 mg, 0.9 mmol) was added in small portions to a stirred solution of 3-ethylsulfanyl-5-fluoro-2-(4-iodophenyl)-1-benzofuran (318 mg, 0.8 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 78%, m.p. 434–435 K; R_f = 0.59 (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 tetrahydrofuran 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. π–π, C—H···O, and I···O interactions (dotted lines) in the crystal structure of the title compound. Cg1 and Cg2 denote the ring centroids. [Symmetry codes: (i) - x, - y + 2, - z + 1; (ii) x + 1/2, - y + 1/2, z - 1/2; (iii) - x, - y +1, - z + 1; (iv) - x + 1, - y + 1, - z + 1; (v) x - 1/2, - y + 3/2, z + 1/2.]

3-Ethylsulfinyl-5-fluoro-2-(4-iodophenyl)-1-benzofuran top

Crystal data top

C₁₆H₁₂FIO₂S	F(000) = 808
M_r = 414.22	D_x = 1.922 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 8330 reflections
a = 7.5384 (4) Å	θ = 2.4–27.5°
b = 9.4104 (5) Å	µ = 2.39 mm⁻¹
c = 20.3049 (9) Å	T = 173 K
β = 96.298 (2)°	Block, colourless
V = 1431.72 (12) Å³	0.24 × 0.18 × 0.16 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD diffractometer	3265 independent reflections
Radiation source: rotating anode	3061 reflections with I > 2σ(I)
Graphite multilayer monochromator	R_int = 0.030
Detector resolution: 10.0 pixels mm^-1	θ_max = 27.5°, θ_min = 2.0°
ϕ and ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −11→12
T_min = 0.658, T_max = 0.680	l = −26→26
12915 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)] = 0.024	Hydrogen site location: difference Fourier map
wR(F²) = 0.062	H-atom parameters constrained
S = 1.13	w = 1/[σ²(F_o²) + (0.0234P)² + 1.1834P] where P = (F_o² + 2F_c²)/3
3265 reflections	(Δ/σ)_max = 0.001
191 parameters	Δρ_max = 0.53 e Å⁻³
0 restraints	Δρ_min = −0.78 e Å⁻³

Crystal data top

C₁₆H₁₂FIO₂S	V = 1431.72 (12) Å³
M_r = 414.22	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.5384 (4) Å	µ = 2.39 mm⁻¹
b = 9.4104 (5) Å	T = 173 K
c = 20.3049 (9) Å	0.24 × 0.18 × 0.16 mm
β = 96.298 (2)°

Data collection top

Bruker SMART APEXII CCD diffractometer	3265 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3061 reflections with I > 2σ(I)
T_min = 0.658, T_max = 0.680	R_int = 0.030
12915 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.024	0 restraints
wR(F²) = 0.062	H-atom parameters constrained
S = 1.13	Δρ_max = 0.53 e Å⁻³
3265 reflections	Δρ_min = −0.78 e Å⁻³
191 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
I	0.410489 (19)	0.499975 (13)	0.189463 (7)	0.02345 (7)
S	0.10698 (7)	0.80859 (5)	0.50166 (2)	0.01980 (11)
F	0.07034 (19)	0.56507 (16)	0.76127 (6)	0.0317 (3)
O1	0.27247 (19)	0.40664 (15)	0.52431 (7)	0.0203 (3)
O2	−0.0186 (2)	0.85501 (17)	0.54905 (8)	0.0283 (3)
C1	0.1851 (3)	0.6367 (2)	0.52771 (10)	0.0183 (4)
C2	0.1707 (3)	0.5743 (2)	0.59203 (10)	0.0184 (4)
C3	0.1180 (3)	0.6214 (2)	0.65229 (10)	0.0210 (4)
H3	0.0824	0.7147	0.6583	0.025*
C4	0.1218 (3)	0.5224 (2)	0.70199 (11)	0.0227 (4)
C5	0.1728 (3)	0.3806 (2)	0.69609 (11)	0.0246 (4)
H5	0.1710	0.3185	0.7316	0.030*
C6	0.2257 (3)	0.3339 (2)	0.63685 (11)	0.0234 (4)
H6	0.2605	0.2403	0.6311	0.028*
C7	0.2246 (3)	0.4326 (2)	0.58651 (10)	0.0191 (4)
C8	0.2457 (3)	0.5318 (2)	0.48905 (10)	0.0181 (4)
C9	0.3111 (3)	0.9094 (2)	0.52147 (11)	0.0242 (4)
H9A	0.4062	0.8643	0.5006	0.029*
H9B	0.2944	1.0041	0.5030	0.029*
C10	0.3674 (3)	0.9214 (3)	0.59512 (11)	0.0296 (5)
H10A	0.2726	0.9633	0.6164	0.044*
H10B	0.4720	0.9799	0.6025	0.044*
H10C	0.3934	0.8285	0.6132	0.044*
C11	0.2883 (3)	0.5241 (2)	0.42083 (11)	0.0185 (4)
C12	0.3152 (3)	0.3921 (2)	0.39142 (10)	0.0215 (4)
H12	0.3078	0.3092	0.4159	0.026*
C13	0.3528 (3)	0.3837 (2)	0.32607 (11)	0.0229 (4)
H13	0.3720	0.2957	0.3072	0.028*
C14	0.3616 (3)	0.5066 (2)	0.28903 (11)	0.0199 (4)
C15	0.3361 (3)	0.6385 (2)	0.31721 (11)	0.0233 (4)
H15	0.3432	0.7209	0.2923	0.028*
C16	0.3001 (3)	0.6469 (2)	0.38255 (11)	0.0234 (4)
H16	0.2834	0.7354	0.4013	0.028*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I	0.02965 (10)	0.02541 (10)	0.01641 (9)	−0.00231 (5)	0.00756 (6)	−0.00183 (4)
S	0.0218 (2)	0.0183 (2)	0.0192 (2)	0.00129 (18)	0.00201 (18)	0.00248 (18)
F	0.0415 (8)	0.0402 (8)	0.0148 (6)	0.0028 (6)	0.0099 (5)	0.0013 (5)
O1	0.0263 (7)	0.0193 (7)	0.0158 (7)	0.0016 (6)	0.0041 (6)	0.0012 (5)
O2	0.0297 (8)	0.0282 (8)	0.0282 (8)	0.0049 (7)	0.0091 (7)	0.0018 (7)
C1	0.0197 (9)	0.0178 (9)	0.0173 (9)	0.0000 (7)	0.0016 (7)	0.0018 (7)
C2	0.0177 (9)	0.0188 (10)	0.0184 (9)	−0.0002 (7)	0.0012 (7)	0.0009 (8)
C3	0.0220 (10)	0.0239 (10)	0.0173 (9)	0.0010 (8)	0.0034 (8)	−0.0009 (8)
C4	0.0232 (10)	0.0305 (11)	0.0149 (10)	−0.0011 (8)	0.0050 (8)	−0.0007 (8)
C5	0.0273 (10)	0.0264 (11)	0.0200 (10)	−0.0012 (9)	0.0022 (8)	0.0078 (8)
C6	0.0264 (10)	0.0206 (10)	0.0230 (10)	0.0005 (8)	0.0018 (8)	0.0033 (8)
C7	0.0196 (9)	0.0204 (10)	0.0175 (9)	−0.0008 (8)	0.0026 (8)	−0.0007 (8)
C8	0.0177 (9)	0.0187 (9)	0.0177 (10)	−0.0010 (7)	0.0010 (8)	0.0023 (8)
C9	0.0254 (10)	0.0225 (10)	0.0252 (11)	−0.0049 (8)	0.0048 (9)	0.0014 (8)
C10	0.0294 (11)	0.0307 (12)	0.0283 (12)	−0.0051 (9)	0.0015 (9)	−0.0041 (9)
C11	0.0165 (9)	0.0230 (10)	0.0163 (10)	0.0000 (7)	0.0026 (7)	−0.0002 (8)
C12	0.0264 (10)	0.0209 (10)	0.0179 (10)	0.0010 (8)	0.0055 (8)	0.0017 (8)
C13	0.0278 (10)	0.0201 (10)	0.0211 (10)	0.0022 (8)	0.0042 (8)	−0.0021 (8)
C14	0.0206 (10)	0.0249 (11)	0.0144 (10)	−0.0008 (7)	0.0026 (8)	−0.0017 (7)
C15	0.0314 (11)	0.0201 (10)	0.0189 (10)	−0.0003 (8)	0.0050 (8)	0.0030 (8)
C16	0.0321 (11)	0.0199 (10)	0.0192 (10)	0.0009 (8)	0.0067 (8)	−0.0023 (8)

Geometric parameters (Å, º) top

I—C14	2.095 (2)	C6—H6	0.9300
I—O2ⁱ	3.2575 (16)	C8—C11	1.458 (3)
S—O2	1.4876 (17)	C9—C10	1.513 (3)
S—C1	1.782 (2)	C9—H9A	0.9700
S—C9	1.815 (2)	C9—H9B	0.9700
F—C4	1.365 (3)	C10—H10A	0.9600
O1—C7	1.373 (2)	C10—H10B	0.9600
O1—C8	1.381 (2)	C10—H10C	0.9600
C1—C8	1.370 (3)	C11—C16	1.401 (3)
C1—C2	1.447 (3)	C11—C12	1.403 (3)
C2—C3	1.399 (3)	C12—C13	1.389 (3)
C2—C7	1.402 (3)	C12—H12	0.9300
C3—C4	1.372 (3)	C13—C14	1.385 (3)
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.397 (3)	C14—C15	1.389 (3)
C5—C6	1.380 (3)	C15—C16	1.385 (3)
C5—H5	0.9300	C15—H15	0.9300
C6—C7	1.380 (3)	C16—H16	0.9300

C14—I—O2ⁱ	153.53 (6)	C10—C9—H9A	108.9
O2—S—C1	106.72 (9)	S—C9—H9A	108.9
O2—S—C9	106.71 (10)	C10—C9—H9B	108.9
C1—S—C9	99.45 (10)	S—C9—H9B	108.9
C7—O1—C8	106.66 (15)	H9A—C9—H9B	107.7
C8—C1—C2	106.71 (18)	C9—C10—H10A	109.5
C8—C1—S	127.16 (16)	C9—C10—H10B	109.5
C2—C1—S	125.55 (15)	H10A—C10—H10B	109.5
C3—C2—C7	118.95 (18)	C9—C10—H10C	109.5
C3—C2—C1	135.82 (19)	H10A—C10—H10C	109.5
C7—C2—C1	105.23 (17)	H10B—C10—H10C	109.5
C4—C3—C2	116.3 (2)	C16—C11—C12	118.3 (2)
C4—C3—H3	121.9	C16—C11—C8	121.35 (19)
C2—C3—H3	121.9	C12—C11—C8	120.38 (19)
F—C4—C3	117.6 (2)	C13—C12—C11	120.73 (19)
F—C4—C5	117.6 (2)	C13—C12—H12	119.6
C3—C4—C5	124.7 (2)	C11—C12—H12	119.6
C6—C5—C4	119.2 (2)	C14—C13—C12	119.9 (2)
C6—C5—H5	120.4	C14—C13—H13	120.1
C4—C5—H5	120.4	C12—C13—H13	120.1
C5—C6—C7	116.9 (2)	C13—C14—C15	120.4 (2)
C5—C6—H6	121.5	C13—C14—I	121.53 (15)
C7—C6—H6	121.5	C15—C14—I	118.10 (15)
O1—C7—C6	125.48 (19)	C16—C15—C14	119.7 (2)
O1—C7—C2	110.53 (17)	C16—C15—H15	120.1
C6—C7—C2	123.98 (19)	C14—C15—H15	120.1
C1—C8—O1	110.86 (18)	C15—C16—C11	121.0 (2)
C1—C8—C11	134.61 (19)	C15—C16—H16	119.5
O1—C8—C11	114.53 (18)	C11—C16—H16	119.5
C10—C9—S	113.40 (16)

O2—S—C1—C8	153.69 (18)	C2—C1—C8—O1	−0.4 (2)
C9—S—C1—C8	−95.6 (2)	S—C1—C8—O1	−171.94 (14)
O2—S—C1—C2	−16.3 (2)	C2—C1—C8—C11	−179.9 (2)
C9—S—C1—C2	94.44 (18)	S—C1—C8—C11	8.6 (4)
C8—C1—C2—C3	−179.7 (2)	C7—O1—C8—C1	1.0 (2)
S—C1—C2—C3	−8.0 (3)	C7—O1—C8—C11	−179.43 (17)
C8—C1—C2—C7	−0.3 (2)	O2—S—C9—C10	42.74 (19)
S—C1—C2—C7	171.38 (15)	C1—S—C9—C10	−68.02 (18)
C7—C2—C3—C4	−0.6 (3)	C1—C8—C11—C16	11.3 (4)
C1—C2—C3—C4	178.7 (2)	O1—C8—C11—C16	−168.10 (19)
C2—C3—C4—F	−179.70 (18)	C1—C8—C11—C12	−167.4 (2)
C2—C3—C4—C5	−0.4 (3)	O1—C8—C11—C12	13.2 (3)
F—C4—C5—C6	−179.96 (19)	C16—C11—C12—C13	0.1 (3)
C3—C4—C5—C6	0.8 (4)	C8—C11—C12—C13	178.88 (19)
C4—C5—C6—C7	0.0 (3)	C11—C12—C13—C14	−0.9 (3)
C8—O1—C7—C6	177.8 (2)	C12—C13—C14—C15	1.1 (3)
C8—O1—C7—C2	−1.2 (2)	C12—C13—C14—I	−178.22 (16)
C5—C6—C7—O1	−179.99 (19)	C13—C14—C15—C16	−0.6 (4)
C5—C6—C7—C2	−1.1 (3)	I—C14—C15—C16	178.77 (17)
C3—C2—C7—O1	−179.52 (17)	C14—C15—C16—C11	−0.2 (3)
C1—C2—C7—O1	1.0 (2)	C12—C11—C16—C15	0.4 (3)
C3—C2—C7—C6	1.4 (3)	C8—C11—C16—C15	−178.3 (2)
C1—C2—C7—C6	−178.09 (19)

Symmetry code: (i) x+1/2, −y+3/2, z−1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9B···O2ⁱⁱ	0.97	2.59	3.337 (3)	134

Symmetry code: (ii) −x, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₂FIO₂S
M_r	414.22
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	173
a, b, c (Å)	7.5384 (4), 9.4104 (5), 20.3049 (9)
β (°)	96.298 (2)
V (Å³)	1431.72 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.39
Crystal size (mm)	0.24 × 0.18 × 0.16

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.658, 0.680
No. of measured, independent and observed [I > 2σ(I)] reflections	12915, 3265, 3061
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.024, 0.062, 1.13
No. of reflections	3265
No. of parameters	191
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.53, −0.78

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
C9—H9B···O2ⁱ	0.97	2.59	3.337 (3)	133.8

Symmetry code: (i) −x, −y+2, −z+1.

References

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Volume 66| Part 7| July 2010| Page o1862

doi:10.1107/S1600536810024736

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