3-(3-Fluoro­phenyl­sulfin­yl)-2,4,6-trimethyl-1-benzofuran

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

doi:10.1107/S1600536811043716

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page o3113

doi:10.1107/S1600536811043716

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3-(3-Fluorophenylsulfinyl)-2,4,6-trimethyl-1-benzofuran

Pil Ja Seo,^a Hong Dae Choi,^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 18 October 2011; accepted 21 October 2011; online 29 October 2011)

In the title compound, C₁₇H₁₅FO₂S, the 3-fluorophenyl ring makes a dihedral angle of 78.38 (4)° with the mean plane of the benzofuran fragment. In the crystal, molecules are linked by weak C—H⋯O and C—H⋯π interactions. The crystal structure also exhibits a slipped π–π interaction between the furan and benzene rings of neighbouring molecules [centroid–centroid distances = 3.628 (2) Å, interplanar distance = 3.417 (2) Å and slippage = 1.219 (2) Å].

Related literature

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 the crystal structures of related compounds, see: Choi et al. (2010a ,b ).

Experimental

Crystal data

C₁₇H₁₅FO₂S
M_r = 302.35
Triclinic, $[P \overline 1]$
a = 6.8561 (2) Å
b = 8.0705 (2) Å
c = 13.9069 (3) Å
α = 103.719 (1)°
β = 91.280 (1)°
γ = 106.973 (1)°
V = 711.50 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 173 K
0.36 × 0.20 × 0.17 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.919, T_max = 0.960
12726 measured reflections
3257 independent reflections
2971 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.098
S = 1.06
3257 reflections
193 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C2–C7 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11B⋯O2ⁱ	0.98	2.30	3.2727 (18)	172
C10—H10A⋯Cg2ⁱⁱ	0.98	2.74	3.655 (2)	155
Symmetry codes: (i) x+1, y, z; (ii) -x+1, -y+1, -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/S1600536811043716/mw2033sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811043716/mw2033Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811043716/mw2033Isup3.cml

checkCIF report

Comment top

Substituted benzofuran derivatives have drawn much attention due 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 study of benzofuran derivatives containing either 3-(4-fluorophenylsulfinyl) (Choi et al., 2010a) or 3-(4-chlorophenylsufinyl) (Choi et al., 2010b) 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 0.019 (1) ° from the least-squares plane defined by the nine constituent atoms. The dihedral angle between the 3-fluorophenyl ring and the mean plane of the benzofuran fragment is 78.38 (4)°. The crystal packing (Fig. 2) is stabilized by weak intermolecular C–H···O and C–H···π interactions (Table 1) as well as by a weak slipped π–π interaction between the furan and benzene rings of adjacent molecules with a Cg1···Cg2ⁱⁱⁱ distance of 3.628 (2) Å and an interplanar distance of 3.417 (2) Å resulting in a slippage of 1.219 (2) Å (Cg1 and Cg2 are the centroids of the C1/C2/C7/O1/C8 furan ring and the C2-C7 benzene ring, respectively).

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 the crystal structures of related compounds, 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)-2,4,6-trimethyl 1-benzofuran (343 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, 2:1 v/v) to afford the title compound as a colorless solid [yield 76%, m.p. 406-407 K; R_f = 0.55 (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 benzene 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 small spheres of arbitrary radius.
	Fig. 2. A view of the C–H···O, C–H···π and π–π interactions (dottedlines) in the crystal structure of the title compound. H atoms non-participating in hydrogen-bonding were omitted for clarity. [Symmetry codes: (i) x + 1 , y, z; (ii) - x + 1, - y + 1, - z + 1; (iii) -x + 1, - y + 2, - z + 1.]

3-(3-Fluorophenylsulfinyl)-2,4,6-trimethyl-1-benzofuran top

Crystal data top

C₁₇H₁₅FO₂S	Z = 2
M_r = 302.35	F(000) = 316
Triclinic, P1	D_x = 1.411 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.8561 (2) Å	Cell parameters from 7579 reflections
b = 8.0705 (2) Å	θ = 2.7–27.5°
c = 13.9069 (3) Å	µ = 0.24 mm⁻¹
α = 103.719 (1)°	T = 173 K
β = 91.280 (1)°	Block, colourless
γ = 106.973 (1)°	0.36 × 0.20 × 0.17 mm
V = 711.50 (3) Å³

Data collection top

Bruker SMART APEXII CCD diffractometer	3257 independent reflections
Radiation source: rotating anode	2971 reflections with I > 2σ(I)
Graphite multilayer monochromator	R_int = 0.023
Detector resolution: 10.0 pixels mm^-1	θ_max = 27.5°, θ_min = 1.5°
ϕ and ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −10→10
T_min = 0.919, T_max = 0.960	l = −16→18
12726 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)] = 0.035	Hydrogen site location: difference Fourier map
wR(F²) = 0.098	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0509P)² + 0.2693P] where P = (F_o² + 2F_c²)/3
3257 reflections	(Δ/σ)_max = 0.001
193 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₁₇H₁₅FO₂S	γ = 106.973 (1)°
M_r = 302.35	V = 711.50 (3) Å³
Triclinic, P1	Z = 2
a = 6.8561 (2) Å	Mo Kα radiation
b = 8.0705 (2) Å	µ = 0.24 mm⁻¹
c = 13.9069 (3) Å	T = 173 K
α = 103.719 (1)°	0.36 × 0.20 × 0.17 mm
β = 91.280 (1)°

Data collection top

Bruker SMART APEXII CCD diffractometer	3257 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2971 reflections with I > 2σ(I)
T_min = 0.919, T_max = 0.960	R_int = 0.023
12726 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.098	H-atom parameters constrained
S = 1.06	Δρ_max = 0.31 e Å⁻³
3257 reflections	Δρ_min = −0.29 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	0.41807 (5)	0.81791 (4)	0.16087 (2)	0.02634 (11)
F1	0.65786 (15)	0.26222 (13)	0.09940 (8)	0.0430 (2)
O1	0.81464 (14)	0.96033 (13)	0.39233 (7)	0.0267 (2)
O2	0.21185 (17)	0.84474 (15)	0.16213 (8)	0.0370 (3)
C1	0.5371 (2)	0.86225 (17)	0.28116 (10)	0.0233 (3)
C2	0.4752 (2)	0.79696 (17)	0.36835 (9)	0.0225 (3)
C3	0.2935 (2)	0.70147 (17)	0.40006 (10)	0.0249 (3)
C4	0.3090 (2)	0.67041 (18)	0.49378 (10)	0.0272 (3)
H4	0.1881	0.6052	0.5167	0.033*
C5	0.4919 (2)	0.72936 (18)	0.55638 (10)	0.0275 (3)
C6	0.6698 (2)	0.82929 (18)	0.52602 (10)	0.0276 (3)
H6	0.7961	0.8739	0.5670	0.033*
C7	0.6540 (2)	0.86042 (17)	0.43328 (10)	0.0240 (3)
C8	0.7386 (2)	0.95919 (17)	0.30056 (10)	0.0250 (3)
C9	0.0898 (2)	0.6369 (2)	0.33833 (12)	0.0338 (3)
H9A	0.0765	0.5220	0.2909	0.051*
H9B	0.0813	0.7251	0.3019	0.051*
H9C	−0.0209	0.6216	0.3819	0.051*
C10	0.4951 (2)	0.6840 (2)	0.65539 (11)	0.0337 (3)
H10A	0.5080	0.5635	0.6458	0.051*
H10B	0.3676	0.6880	0.6849	0.051*
H10C	0.6119	0.7710	0.6998	0.051*
C11	0.8879 (2)	1.0612 (2)	0.24364 (12)	0.0327 (3)
H11A	0.8162	1.0663	0.1831	0.049*
H11B	0.9924	1.0016	0.2255	0.049*
H11C	0.9535	1.1832	0.2847	0.049*
C12	0.3746 (2)	0.57927 (18)	0.12654 (9)	0.0239 (3)
C13	0.1800 (2)	0.4675 (2)	0.08789 (11)	0.0309 (3)
H13	0.0697	0.5155	0.0843	0.037*
C14	0.1480 (2)	0.2839 (2)	0.05441 (12)	0.0365 (3)
H14	0.0148	0.2062	0.0282	0.044*
C15	0.3083 (2)	0.2136 (2)	0.05897 (11)	0.0342 (3)
H15	0.2871	0.0883	0.0368	0.041*
C16	0.4994 (2)	0.33028 (19)	0.09652 (10)	0.0291 (3)
C17	0.5392 (2)	0.51277 (18)	0.13067 (10)	0.0257 (3)
H17	0.6733	0.5897	0.1559	0.031*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.03275 (19)	0.02625 (19)	0.02560 (18)	0.01438 (14)	0.00475 (13)	0.01027 (13)
F1	0.0476 (5)	0.0378 (5)	0.0512 (6)	0.0265 (4)	0.0033 (4)	0.0091 (4)
O1	0.0243 (5)	0.0270 (5)	0.0291 (5)	0.0065 (4)	0.0055 (4)	0.0090 (4)
O2	0.0390 (6)	0.0406 (6)	0.0410 (6)	0.0246 (5)	0.0023 (5)	0.0131 (5)
C1	0.0275 (6)	0.0211 (6)	0.0243 (6)	0.0105 (5)	0.0065 (5)	0.0072 (5)
C2	0.0275 (6)	0.0191 (6)	0.0230 (6)	0.0103 (5)	0.0058 (5)	0.0053 (5)
C3	0.0268 (6)	0.0205 (6)	0.0282 (6)	0.0084 (5)	0.0064 (5)	0.0059 (5)
C4	0.0308 (7)	0.0228 (6)	0.0296 (7)	0.0083 (5)	0.0102 (5)	0.0087 (5)
C5	0.0380 (7)	0.0230 (6)	0.0245 (6)	0.0132 (6)	0.0081 (5)	0.0065 (5)
C6	0.0309 (7)	0.0260 (7)	0.0256 (6)	0.0098 (5)	0.0022 (5)	0.0049 (5)
C7	0.0260 (6)	0.0198 (6)	0.0266 (6)	0.0076 (5)	0.0069 (5)	0.0056 (5)
C8	0.0288 (6)	0.0222 (6)	0.0275 (6)	0.0116 (5)	0.0081 (5)	0.0077 (5)
C9	0.0266 (7)	0.0377 (8)	0.0364 (8)	0.0053 (6)	0.0041 (6)	0.0140 (6)
C10	0.0457 (8)	0.0340 (8)	0.0269 (7)	0.0167 (6)	0.0083 (6)	0.0119 (6)
C11	0.0302 (7)	0.0338 (8)	0.0402 (8)	0.0117 (6)	0.0134 (6)	0.0179 (6)
C12	0.0294 (6)	0.0253 (6)	0.0199 (6)	0.0108 (5)	0.0045 (5)	0.0082 (5)
C13	0.0278 (7)	0.0373 (8)	0.0286 (7)	0.0108 (6)	0.0026 (5)	0.0096 (6)
C14	0.0326 (7)	0.0347 (8)	0.0353 (8)	0.0009 (6)	0.0028 (6)	0.0075 (6)
C15	0.0463 (9)	0.0246 (7)	0.0302 (7)	0.0073 (6)	0.0076 (6)	0.0081 (6)
C16	0.0370 (7)	0.0313 (7)	0.0257 (6)	0.0176 (6)	0.0061 (5)	0.0105 (6)
C17	0.0280 (6)	0.0276 (7)	0.0230 (6)	0.0103 (5)	0.0025 (5)	0.0072 (5)

Geometric parameters (Å, º) top

S1—O2	1.4914 (11)	C9—H9A	0.9800
S1—C1	1.7542 (14)	C9—H9B	0.9800
S1—C12	1.8023 (14)	C9—H9C	0.9800
F1—C16	1.3567 (16)	C10—H10A	0.9800
O1—C8	1.3648 (16)	C10—H10B	0.9800
O1—C7	1.3839 (15)	C10—H10C	0.9800
C1—C8	1.3584 (19)	C11—H11A	0.9800
C1—C2	1.4573 (17)	C11—H11B	0.9800
C2—C7	1.3947 (19)	C11—H11C	0.9800
C2—C3	1.4019 (18)	C12—C13	1.385 (2)
C3—C4	1.3918 (19)	C12—C17	1.3897 (18)
C3—C9	1.5059 (19)	C13—C14	1.392 (2)
C4—C5	1.401 (2)	C13—H13	0.9500
C4—H4	0.9500	C14—C15	1.383 (2)
C5—C6	1.388 (2)	C14—H14	0.9500
C5—C10	1.5075 (18)	C15—C16	1.375 (2)
C6—C7	1.3790 (19)	C15—H15	0.9500
C6—H6	0.9500	C16—C17	1.377 (2)
C8—C11	1.4851 (18)	C17—H17	0.9500

O2—S1—C1	112.14 (6)	H9A—C9—H9C	109.5
O2—S1—C12	106.48 (7)	H9B—C9—H9C	109.5
C1—S1—C12	97.57 (6)	C5—C10—H10A	109.5
C8—O1—C7	106.56 (10)	C5—C10—H10B	109.5
C8—C1—C2	107.30 (12)	H10A—C10—H10B	109.5
C8—C1—S1	118.53 (10)	C5—C10—H10C	109.5
C2—C1—S1	133.60 (10)	H10A—C10—H10C	109.5
C7—C2—C3	118.64 (12)	H10B—C10—H10C	109.5
C7—C2—C1	104.16 (11)	C8—C11—H11A	109.5
C3—C2—C1	137.13 (12)	C8—C11—H11B	109.5
C4—C3—C2	116.41 (12)	H11A—C11—H11B	109.5
C4—C3—C9	120.70 (12)	C8—C11—H11C	109.5
C2—C3—C9	122.88 (12)	H11A—C11—H11C	109.5
C3—C4—C5	124.05 (12)	H11B—C11—H11C	109.5
C3—C4—H4	118.0	C13—C12—C17	121.50 (13)
C5—C4—H4	118.0	C13—C12—S1	118.67 (10)
C6—C5—C4	119.25 (12)	C17—C12—S1	119.56 (10)
C6—C5—C10	120.47 (13)	C12—C13—C14	119.16 (13)
C4—C5—C10	120.28 (13)	C12—C13—H13	120.4
C7—C6—C5	116.58 (13)	C14—C13—H13	120.4
C7—C6—H6	121.7	C15—C14—C13	120.62 (14)
C5—C6—H6	121.7	C15—C14—H14	119.7
C6—C7—O1	124.21 (12)	C13—C14—H14	119.7
C6—C7—C2	124.97 (12)	C16—C15—C14	118.08 (14)
O1—C7—C2	110.81 (11)	C16—C15—H15	121.0
C1—C8—O1	111.15 (11)	C14—C15—H15	121.0
C1—C8—C11	133.60 (13)	F1—C16—C15	118.27 (13)
O1—C8—C11	115.25 (12)	F1—C16—C17	118.10 (13)
C3—C9—H9A	109.5	C15—C16—C17	123.62 (13)
C3—C9—H9B	109.5	C16—C17—C12	117.01 (13)
H9A—C9—H9B	109.5	C16—C17—H17	121.5
C3—C9—H9C	109.5	C12—C17—H17	121.5

O2—S1—C1—C8	−136.09 (11)	C1—C2—C7—C6	−179.12 (12)
C12—S1—C1—C8	112.63 (11)	C3—C2—C7—O1	−176.35 (11)
O2—S1—C1—C2	53.83 (14)	C1—C2—C7—O1	1.16 (14)
C12—S1—C1—C2	−57.46 (13)	C2—C1—C8—O1	1.05 (15)
C8—C1—C2—C7	−1.32 (14)	S1—C1—C8—O1	−171.44 (8)
S1—C1—C2—C7	169.56 (11)	C2—C1—C8—C11	−178.84 (14)
C8—C1—C2—C3	175.47 (15)	S1—C1—C8—C11	8.7 (2)
S1—C1—C2—C3	−13.7 (2)	C7—O1—C8—C1	−0.33 (14)
C7—C2—C3—C4	−2.87 (18)	C7—O1—C8—C11	179.58 (11)
C1—C2—C3—C4	−179.32 (14)	O2—S1—C12—C13	13.52 (12)
C7—C2—C3—C9	176.19 (13)	C1—S1—C12—C13	129.35 (11)
C1—C2—C3—C9	−0.3 (2)	O2—S1—C12—C17	−172.39 (10)
C2—C3—C4—C5	0.5 (2)	C1—S1—C12—C17	−56.55 (11)
C9—C3—C4—C5	−178.63 (13)	C17—C12—C13—C14	1.4 (2)
C3—C4—C5—C6	1.8 (2)	S1—C12—C13—C14	175.37 (11)
C3—C4—C5—C10	−177.97 (12)	C12—C13—C14—C15	−0.4 (2)
C4—C5—C6—C7	−1.44 (19)	C13—C14—C15—C16	−0.6 (2)
C10—C5—C6—C7	178.32 (12)	C14—C15—C16—F1	−178.79 (12)
C5—C6—C7—O1	178.58 (12)	C14—C15—C16—C17	0.7 (2)
C5—C6—C7—C2	−1.1 (2)	F1—C16—C17—C12	179.73 (11)
C8—O1—C7—C6	179.71 (12)	C15—C16—C17—C12	0.3 (2)
C8—O1—C7—C2	−0.57 (14)	C13—C12—C17—C16	−1.32 (19)
C3—C2—C7—C6	3.4 (2)	S1—C12—C17—C16	−175.24 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11B···O2ⁱ	0.98	2.30	3.2727 (18)	172
C10—H10A···Cg2ⁱⁱ	0.98	2.74	3.655 (2)	155

Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₅FO₂S
M_r	302.35
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	6.8561 (2), 8.0705 (2), 13.9069 (3)
α, β, γ (°)	103.719 (1), 91.280 (1), 106.973 (1)
V (Å³)	711.50 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.36 × 0.20 × 0.17

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.919, 0.960
No. of measured, independent and observed [I > 2σ(I)] reflections	12726, 3257, 2971
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.098, 1.06
No. of reflections	3257
No. of parameters	193
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.29

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
C11—H11B···O2ⁱ	0.98	2.30	3.2727 (18)	172.2
C10—H10A···Cg2ⁱⁱ	0.98	2.74	3.655 (2)	155.3

Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y+1, −z+1.

References

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Volume 67| Part 11| November 2011| Page o3113

doi:10.1107/S1600536811043716

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