5-Bromo-3-cyclo­hexyl­sulfinyl-2,7-dimethyl-1-benzofuran

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

doi:10.1107/S1600536811011354

organic compounds

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ISSN: 2056-9890

Volume 67| Part 5| May 2011| Page o1039

doi:10.1107/S1600536811011354

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5-Bromo-3-cyclohexylsulfinyl-2,7-dimethyl-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 21 March 2011; accepted 27 March 2011; online 7 April 2011)

In the title compound, C₁₆H₁₉BrO₂S, the cyclohexyl ring adopts a chair conformation. In the crystal, molecules are linked by a Br⋯Br [3.5994 (5) Å] contact and a C—H⋯π interaction involving the phenyl ring of the benzofuran. The crystal structure also exhibits a slipped π–π interaction between the furan rings of neighbouring molecules [centroid–centroid distance = 3.767 (1) Å and interplanar distance of 3.452 (1) Å with a slippage of 1.508 Å].

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 structural studies of the related 5-bromo-3-cyclohexylsulfinyl-2-methyl-1-benzofuran, see: Choi et al. (2011 ).

Experimental

Crystal data

C₁₆H₁₉BrO₂S
M_r = 355.28
Triclinic, $[P \overline 1]$
a = 6.3957 (2) Å
b = 11.2576 (3) Å
c = 12.0384 (3) Å
α = 104.726 (2)°
β = 101.426 (1)°
γ = 106.380 (1)°
V = 769.53 (4) Å³
Z = 2
Mo Kα radiation
μ = 2.81 mm⁻¹
T = 173 K
0.19 × 0.17 × 0.09 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.660, T_max = 0.746
14554 measured reflections
3887 independent reflections
3165 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.077
S = 1.03
3887 reflections
183 parameters
H-atom parameters constrained
Δρ_max = 0.46 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the phenyl ring of the benzofuran.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10B⋯Cg1ⁱ	0.98	2.97	3.717 (2)	134
Symmetry code: (i) -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/S1600536811011354/dn2669sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811011354/dn2669Isup2.hkl

checkCIF report

Comment top

Many compounds having a benzofuran skeleton have attracted interesting 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 3-cyclohexylsulfinyl-5-halo-2-methyl-1-benzofuran analogues (Choi et al., 2011), 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 0.010 (1) Å from the least-squares plane defined by the nine constituent atoms. The crystal packing (Fig. 2) is stabilized by an intermolecular Br1···Br1ⁱ contact at 3.5994 (5) Å, and by a weak intermolecular C—H···π interaction (Table 1, Cg1 is the centroid of the C2–C7 phenyl ring of the benzofuran). The crystal packing (Fig. 2) is further stabilized by a weak slippest π···π interaction between the furan rings of neighbouring molecules, with a Cg2···Cg2ⁱⁱ distance of 3.767 (1) Å and an interplanar distance of 3.452 (1) Å resulting in a slippage of 1.508 Å (Cg2 is the centroid of the C1/C2/C7/O1/C8 furan ring).

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 structural studies of the related 5-bromo-3-cyclohexylsulfinyl-2-methyl-1-benzofuran, see: Choi et al. (2011).

Experimental top

77% 3-chloroperoxybenzoic acid (269 mg, 1.2 mmol) was added in small portions to a stirred solution of 5-bromo-3-cyclohexylsulfanyl-2,7-dimethyl-1-benzofuran (373 mg, 1.1 mmol) in dichloromethane (40 mL) at 273 K. After being stirred at room temperature for 3h, 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 75%, m.p. 415–416 K; R_f = 0.61 (hexane–ethyl acetate, 2:1 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.

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

5-Bromo-3-cyclohexylsulfinyl-2,7-dimethyl-1-benzofuran top

Crystal data top

C₁₆H₁₉BrO₂S	Z = 2
M_r = 355.28	F(000) = 364
Triclinic, P1	D_x = 1.533 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.3957 (2) Å	Cell parameters from 5547 reflections
b = 11.2576 (3) Å	θ = 3.1–28.1°
c = 12.0384 (3) Å	µ = 2.81 mm⁻¹
α = 104.726 (2)°	T = 173 K
β = 101.426 (1)°	Block, colourless
γ = 106.380 (1)°	0.19 × 0.17 × 0.09 mm
V = 769.53 (4) Å³

Data collection top

Bruker SMART APEXII CCD diffractometer	3887 independent reflections
Radiation source: rotating anode	3165 reflections with I > 2σ(I)
Graphite multilayer monochromator	R_int = 0.032
Detector resolution: 10.0 pixels mm^-1	θ_max = 28.6°, θ_min = 1.8°
ϕ and ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −15→15
T_min = 0.660, T_max = 0.746	l = −15→16
14554 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)] = 0.030	Hydrogen site location: difference Fourier map
wR(F²) = 0.077	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0379P)² + 0.1985P] where P = (F_o² + 2F_c²)/3
3887 reflections	(Δ/σ)_max < 0.001
183 parameters	Δρ_max = 0.46 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₁₆H₁₉BrO₂S	γ = 106.380 (1)°
M_r = 355.28	V = 769.53 (4) Å³
Triclinic, P1	Z = 2
a = 6.3957 (2) Å	Mo Kα radiation
b = 11.2576 (3) Å	µ = 2.81 mm⁻¹
c = 12.0384 (3) Å	T = 173 K
α = 104.726 (2)°	0.19 × 0.17 × 0.09 mm
β = 101.426 (1)°

Data collection top

Bruker SMART APEXII CCD diffractometer	3887 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3165 reflections with I > 2σ(I)
T_min = 0.660, T_max = 0.746	R_int = 0.032
14554 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	0 restraints
wR(F²) = 0.077	H-atom parameters constrained
S = 1.03	Δρ_max = 0.46 e Å⁻³
3887 reflections	Δρ_min = −0.30 e Å⁻³
183 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
Br1	−0.29117 (3)	0.05949 (2)	0.42781 (2)	0.04566 (9)
S1	0.59311 (8)	0.44037 (4)	0.82300 (4)	0.02878 (11)
O1	0.6631 (2)	0.39267 (13)	0.49722 (12)	0.0317 (3)
O2	0.3652 (2)	0.44013 (15)	0.83380 (13)	0.0419 (3)
C1	0.5706 (3)	0.40074 (17)	0.66863 (16)	0.0274 (4)
C2	0.3721 (3)	0.31269 (17)	0.57099 (16)	0.0267 (4)
C3	0.1515 (3)	0.23721 (17)	0.56098 (17)	0.0292 (4)
H3	0.0991	0.2367	0.6295	0.035*
C4	0.0127 (3)	0.16314 (18)	0.44627 (18)	0.0326 (4)
C5	0.0853 (3)	0.16066 (19)	0.34375 (18)	0.0348 (4)
H5	−0.0172	0.1066	0.2670	0.042*
C6	0.3041 (3)	0.23572 (19)	0.35242 (17)	0.0328 (4)
C7	0.4401 (3)	0.31112 (18)	0.46765 (17)	0.0294 (4)
C8	0.7373 (3)	0.44626 (17)	0.62025 (17)	0.0291 (4)
C9	0.3937 (4)	0.2351 (2)	0.24595 (18)	0.0441 (5)
H9A	0.2719	0.1783	0.1722	0.066*
H9B	0.5203	0.2021	0.2532	0.066*
H9C	0.4472	0.3245	0.2430	0.066*
C10	0.9769 (3)	0.53593 (19)	0.67278 (19)	0.0356 (4)
H10A	1.0015	0.5858	0.7568	0.053*
H10B	1.0100	0.5967	0.6276	0.053*
H10C	1.0781	0.4848	0.6688	0.053*
C11	0.6185 (3)	0.28811 (17)	0.84033 (16)	0.0272 (4)
H11	0.4882	0.2124	0.7792	0.033*
C12	0.6042 (5)	0.2884 (2)	0.96458 (19)	0.0467 (5)
H12A	0.4538	0.2901	0.9724	0.056*
H12B	0.7234	0.3675	1.0260	0.056*
C13	0.6374 (6)	0.1651 (3)	0.9844 (2)	0.0619 (7)
H13A	0.6342	0.1671	1.0667	0.074*
H13B	0.5101	0.0867	0.9272	0.074*
C14	0.8601 (5)	0.1549 (2)	0.9674 (2)	0.0578 (7)
H14A	0.9883	0.2295	1.0288	0.069*
H14B	0.8736	0.0728	0.9784	0.069*
C15	0.8734 (4)	0.1555 (2)	0.8440 (2)	0.0482 (6)
H15A	0.7550	0.0757	0.7831	0.058*
H15B	1.0239	0.1537	0.8364	0.058*
C16	0.8397 (4)	0.2765 (2)	0.8201 (2)	0.0447 (5)
H16A	0.9689	0.3559	0.8741	0.054*
H16B	0.8369	0.2704	0.7362	0.054*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.02694 (11)	0.03510 (12)	0.06310 (16)	0.00642 (8)	0.00168 (9)	0.01043 (10)
S1	0.0298 (2)	0.0258 (2)	0.0286 (2)	0.01108 (18)	0.00634 (18)	0.00554 (17)
O1	0.0329 (7)	0.0338 (7)	0.0342 (7)	0.0138 (6)	0.0130 (6)	0.0160 (6)
O2	0.0401 (8)	0.0503 (8)	0.0411 (8)	0.0274 (7)	0.0152 (7)	0.0090 (7)
C1	0.0263 (8)	0.0269 (8)	0.0303 (9)	0.0115 (7)	0.0074 (7)	0.0099 (7)
C2	0.0288 (9)	0.0240 (8)	0.0294 (9)	0.0135 (7)	0.0068 (7)	0.0089 (7)
C3	0.0280 (9)	0.0283 (8)	0.0352 (10)	0.0139 (7)	0.0104 (7)	0.0116 (7)
C4	0.0255 (8)	0.0260 (8)	0.0441 (11)	0.0116 (7)	0.0042 (8)	0.0096 (8)
C5	0.0378 (10)	0.0302 (9)	0.0336 (10)	0.0172 (8)	0.0015 (8)	0.0066 (8)
C6	0.0414 (10)	0.0326 (9)	0.0301 (10)	0.0215 (8)	0.0085 (8)	0.0120 (8)
C7	0.0321 (9)	0.0291 (8)	0.0324 (10)	0.0153 (8)	0.0099 (8)	0.0135 (7)
C8	0.0302 (9)	0.0273 (8)	0.0327 (10)	0.0126 (7)	0.0077 (7)	0.0129 (7)
C9	0.0583 (14)	0.0483 (12)	0.0298 (10)	0.0230 (11)	0.0128 (10)	0.0147 (9)
C10	0.0286 (9)	0.0327 (9)	0.0464 (12)	0.0095 (8)	0.0109 (8)	0.0156 (9)
C11	0.0284 (9)	0.0241 (8)	0.0285 (9)	0.0093 (7)	0.0093 (7)	0.0070 (7)
C12	0.0718 (16)	0.0448 (12)	0.0364 (11)	0.0302 (12)	0.0247 (11)	0.0171 (10)
C13	0.107 (2)	0.0588 (15)	0.0489 (14)	0.0436 (16)	0.0409 (15)	0.0349 (13)
C14	0.0807 (19)	0.0438 (12)	0.0458 (13)	0.0323 (13)	−0.0038 (12)	0.0149 (10)
C15	0.0461 (12)	0.0492 (13)	0.0619 (15)	0.0308 (11)	0.0163 (11)	0.0229 (11)
C16	0.0388 (11)	0.0510 (12)	0.0653 (15)	0.0273 (10)	0.0260 (11)	0.0325 (11)

Geometric parameters (Å, º) top

Br1—C4	1.8987 (19)	C9—H9C	0.9800
Br1—Br1ⁱ	3.5994 (5)	C10—H10A	0.9800
S1—O2	1.4885 (14)	C10—H10B	0.9800
S1—C1	1.7634 (19)	C10—H10C	0.9800
S1—C11	1.8259 (18)	C11—C12	1.516 (3)
O1—C8	1.374 (2)	C11—C16	1.517 (3)
O1—C7	1.378 (2)	C11—H11	1.0000
C1—C8	1.352 (3)	C12—C13	1.530 (3)
C1—C2	1.443 (2)	C12—H12A	0.9900
C2—C3	1.390 (3)	C12—H12B	0.9900
C2—C7	1.395 (3)	C13—C14	1.510 (4)
C3—C4	1.379 (3)	C13—H13A	0.9900
C3—H3	0.9500	C13—H13B	0.9900
C4—C5	1.399 (3)	C14—C15	1.507 (3)
C5—C6	1.383 (3)	C14—H14A	0.9900
C5—H5	0.9500	C14—H14B	0.9900
C6—C7	1.381 (3)	C15—C16	1.526 (3)
C6—C9	1.503 (3)	C15—H15A	0.9900
C8—C10	1.479 (3)	C15—H15B	0.9900
C9—H9A	0.9800	C16—H16A	0.9900
C9—H9B	0.9800	C16—H16B	0.9900

C4—Br1—Br1ⁱ	147.22 (6)	H10A—C10—H10C	109.5
O2—S1—C1	106.24 (8)	H10B—C10—H10C	109.5
O2—S1—C11	107.06 (9)	C12—C11—C16	112.33 (17)
C1—S1—C11	97.42 (8)	C12—C11—S1	107.98 (13)
C8—O1—C7	106.57 (14)	C16—C11—S1	109.89 (13)
C8—C1—C2	107.53 (16)	C12—C11—H11	108.9
C8—C1—S1	126.17 (14)	C16—C11—H11	108.9
C2—C1—S1	126.30 (14)	S1—C11—H11	108.9
C3—C2—C7	119.63 (17)	C11—C12—C13	109.28 (18)
C3—C2—C1	135.63 (18)	C11—C12—H12A	109.8
C7—C2—C1	104.75 (16)	C13—C12—H12A	109.8
C4—C3—C2	116.39 (18)	C11—C12—H12B	109.8
C4—C3—H3	121.8	C13—C12—H12B	109.8
C2—C3—H3	121.8	H12A—C12—H12B	108.3
C3—C4—C5	123.19 (18)	C14—C13—C12	111.7 (2)
C3—C4—Br1	117.98 (15)	C14—C13—H13A	109.3
C5—C4—Br1	118.83 (14)	C12—C13—H13A	109.3
C6—C5—C4	120.99 (18)	C14—C13—H13B	109.3
C6—C5—H5	119.5	C12—C13—H13B	109.3
C4—C5—H5	119.5	H13A—C13—H13B	107.9
C7—C6—C5	115.22 (18)	C15—C14—C13	110.68 (19)
C7—C6—C9	121.3 (2)	C15—C14—H14A	109.5
C5—C6—C9	123.49 (19)	C13—C14—H14A	109.5
O1—C7—C6	125.06 (17)	C15—C14—H14B	109.5
O1—C7—C2	110.37 (16)	C13—C14—H14B	109.5
C6—C7—C2	124.55 (18)	H14A—C14—H14B	108.1
C1—C8—O1	110.78 (16)	C14—C15—C16	111.53 (19)
C1—C8—C10	133.19 (18)	C14—C15—H15A	109.3
O1—C8—C10	116.00 (16)	C16—C15—H15A	109.3
C6—C9—H9A	109.5	C14—C15—H15B	109.3
C6—C9—H9B	109.5	C16—C15—H15B	109.3
H9A—C9—H9B	109.5	H15A—C15—H15B	108.0
C6—C9—H9C	109.5	C11—C16—C15	110.72 (18)
H9A—C9—H9C	109.5	C11—C16—H16A	109.5
H9B—C9—H9C	109.5	C15—C16—H16A	109.5
C8—C10—H10A	109.5	C11—C16—H16B	109.5
C8—C10—H10B	109.5	C15—C16—H16B	109.5
H10A—C10—H10B	109.5	H16A—C16—H16B	108.1
C8—C10—H10C	109.5

O2—S1—C1—C8	146.51 (16)	C9—C6—C7—C2	−177.25 (17)
C11—S1—C1—C8	−103.24 (17)	C3—C2—C7—O1	179.67 (15)
O2—S1—C1—C2	−34.29 (17)	C1—C2—C7—O1	−0.58 (19)
C11—S1—C1—C2	75.95 (16)	C3—C2—C7—C6	−1.8 (3)
C8—C1—C2—C3	−179.44 (19)	C1—C2—C7—C6	177.92 (17)
S1—C1—C2—C3	1.2 (3)	C2—C1—C8—O1	−0.9 (2)
C8—C1—C2—C7	0.88 (19)	S1—C1—C8—O1	178.45 (12)
S1—C1—C2—C7	−178.44 (13)	C2—C1—C8—C10	−178.65 (19)
C7—C2—C3—C4	0.6 (2)	S1—C1—C8—C10	0.7 (3)
C1—C2—C3—C4	−179.02 (18)	C7—O1—C8—C1	0.51 (19)
C2—C3—C4—C5	0.7 (3)	C7—O1—C8—C10	178.71 (15)
C2—C3—C4—Br1	−179.46 (12)	O2—S1—C11—C12	−61.81 (16)
Br1ⁱ—Br1—C4—C3	−6.1 (2)	C1—S1—C11—C12	−171.38 (15)
Br1ⁱ—Br1—C4—C5	173.74 (9)	O2—S1—C11—C16	175.35 (14)
C3—C4—C5—C6	−1.0 (3)	C1—S1—C11—C16	65.79 (15)
Br1—C4—C5—C6	179.16 (14)	C16—C11—C12—C13	−55.8 (3)
C4—C5—C6—C7	−0.1 (3)	S1—C11—C12—C13	−177.09 (19)
C4—C5—C6—C9	178.64 (18)	C11—C12—C13—C14	56.7 (3)
C8—O1—C7—C6	−178.41 (17)	C12—C13—C14—C15	−57.4 (3)
C8—O1—C7—C2	0.08 (19)	C13—C14—C15—C16	55.9 (3)
C5—C6—C7—O1	179.78 (16)	C12—C11—C16—C15	55.2 (2)
C9—C6—C7—O1	1.0 (3)	S1—C11—C16—C15	175.44 (16)
C5—C6—C7—C2	1.5 (3)	C14—C15—C16—C11	−54.6 (3)

Symmetry code: (i) −x−1, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the phenyl ring of the benzofuran.

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10B···Cg1ⁱⁱ	0.98	2.97	3.717 (2)	134

Symmetry code: (ii) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₉BrO₂S
M_r	355.28
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	6.3957 (2), 11.2576 (3), 12.0384 (3)
α, β, γ (°)	104.726 (2), 101.426 (1), 106.380 (1)
V (Å³)	769.53 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.81
Crystal size (mm)	0.19 × 0.17 × 0.09

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.660, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	14554, 3887, 3165
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.672

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.077, 1.03
No. of reflections	3887
No. of parameters	183
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.46, −0.30

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

Cg1 is the centroid of the phenyl ring of the benzofuran.

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10B···Cg1ⁱ	0.98	2.97	3.717 (2)	134

Symmetry code: (i) −x+1, −y+1, −z+1.

References

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Volume 67| Part 5| May 2011| Page o1039

doi:10.1107/S1600536811011354

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