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

Choi, H.D.; Seo, P.J.; Lee, U.

doi:10.1107/S1600536812001547

organic compounds

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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Page o456

doi:10.1107/S1600536812001547

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

Hong Dae Choi,^a Pil Ja Seo ^a 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 3 January 2012; accepted 13 January 2012; online 18 January 2012)

In the title compound, C₁₇H₁₅BrO₂S, the 4-bromophenyl ring makes a dihedral angle of 87.12 (6)° with the mean plane of the benzofuran fragment. In the crystal, molecules are linked by weak C—H⋯O and C—H⋯π interactions.

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

C₁₇H₁₅BrO₂S
M_r = 363.26
Orthorhombic, P n a 2₁
a = 12.0911 (3) Å
b = 19.4713 (3) Å
c = 6.4482 (1) Å
V = 1518.10 (5) Å³
Z = 4
Mo Kα radiation
μ = 2.85 mm⁻¹
T = 173 K
0.33 × 0.29 × 0.19 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.456, T_max = 0.611
8258 measured reflections
3190 independent reflections
2797 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.078
S = 1.03
3190 reflections
194 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.55 e Å⁻³
Absolute structure: Flack (1983 ), 1131 Friedel pairs
Flack parameter: 0.014 (12)

Table 1
Hydrogen-bond geometry (Å, °)

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11C⋯O2ⁱ	0.98	2.59	3.343 (3)	134
C17—H17⋯O2ⁱ	0.95	2.56	3.432 (3)	153
C4—H4⋯Cgⁱⁱ	0.95	2.89	3.724 (3)	147
C11—H11A⋯Cgⁱⁱⁱ	0.98	2.98	3.917 (3)	161
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z]$ ; (ii) $[-x+1, -y, z+{\script{1\over 2}}]$ ; (iii) x, y, 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/S1600536812001547/pk2381sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812001547/pk2381Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812001547/pk2381Isup3.cml

checkCIF report

Comment top

Many compounds involving benzofuran skeleton have drawn much attention owing to their valuable biological 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 2,4,6-trimethyl-1-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 0.009 (2) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle between the 4-bromophenyl ring and the mean plane of the benzofurn fragment is 87.12 (6)°. The crystal packing (Fig. 2) is stabilized by weak intermolecular C—H···O hydrogen bonds (see Table 1; first & second entry). The crystal packing (Fig. 3) is further stabilized by intermolecular C—H···π interactions (see Table 1; third & fourth entry, Cg is the centroid of the C2–C7 benzene ring).

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 (224 mg, 1.0 mmol) was added in small portions to a stirred solution of 3-(4-bromophenylsulfanyl)-2, 4, 6-trimethyl 1-benzofuran (312 mg, 0.9 mmol) in dichloromethane (40 mL) at 273 K. After being stirred at room temperature for 5h, 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 73%, m.p. 459–461 K; R_f = 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 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. 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 interactions (dotted lines) in the crystal structure of the title compound. H atoms not participating in hydrogen-bonding were omitted for clarity. [Symmetry codes: (i) x - 1/2, - y + 1/2, z; (iv) x + 1/2, - y + 1/2, z.]
	Fig. 3. A view of the C—H···π interactions (dotted lines) in the crystal structure of the title compound. H atoms not participating in hydrogen-bonding were omitted for clarity. [Symmetry codes: (ii) - x + 1, - y, z + 1/2; (iii) x, y, z - 1; (v) - x + 1, - y, z - 1/2; (vi) x, y, z + 1.]

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

Crystal data top

C₁₇H₁₅BrO₂S	F(000) = 736
M_r = 363.26	D_x = 1.589 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 3220 reflections
a = 12.0911 (3) Å	θ = 2.7–27.0°
b = 19.4713 (3) Å	µ = 2.85 mm⁻¹
c = 6.4482 (1) Å	T = 173 K
V = 1518.10 (5) Å³	Block, colourless
Z = 4	0.33 × 0.29 × 0.19 mm

Data collection top

Bruker SMART APEXII CCD diffractometer	3190 independent reflections
Radiation source: rotating anode	2797 reflections with I > 2σ(I)
Multilayer monochromator	R_int = 0.030
Detector resolution: 10.0 pixels mm^-1	θ_max = 28.3°, θ_min = 2.0°
ϕ and ω scans	h = −11→16
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −25→21
T_min = 0.456, T_max = 0.611	l = −8→7
8258 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.032	H-atom parameters constrained
wR(F²) = 0.078	w = 1/[σ²(F_o²) + (0.0362P)²] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
3190 reflections	Δρ_max = 0.24 e Å⁻³
194 parameters	Δρ_min = −0.55 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1131 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.014 (12)

Crystal data top

C₁₇H₁₅BrO₂S	V = 1518.10 (5) Å³
M_r = 363.26	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 12.0911 (3) Å	µ = 2.85 mm⁻¹
b = 19.4713 (3) Å	T = 173 K
c = 6.4482 (1) Å	0.33 × 0.29 × 0.19 mm

Data collection top

Bruker SMART APEXII CCD diffractometer	3190 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2797 reflections with I > 2σ(I)
T_min = 0.456, T_max = 0.611	R_int = 0.030
8258 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	H-atom parameters constrained
wR(F²) = 0.078	Δρ_max = 0.24 e Å⁻³
S = 1.03	Δρ_min = −0.55 e Å⁻³
3190 reflections	Absolute structure: Flack (1983), 1131 Friedel pairs
194 parameters	Absolute structure parameter: 0.014 (12)
1 restraint

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	0.50103 (3)	0.448031 (17)	0.95844 (11)	0.04606 (11)
S1	0.59546 (5)	0.24377 (3)	0.19734 (12)	0.02620 (14)
O1	0.32864 (13)	0.13364 (8)	0.1240 (3)	0.0271 (4)
O2	0.70481 (13)	0.21095 (9)	0.2396 (3)	0.0337 (4)
C1	0.48796 (18)	0.18334 (13)	0.2236 (4)	0.0232 (5)
C2	0.4617 (2)	0.13067 (12)	0.3768 (4)	0.0218 (5)
C3	0.50764 (18)	0.10532 (15)	0.5613 (5)	0.0244 (6)
C4	0.4501 (2)	0.05337 (12)	0.6611 (4)	0.0280 (6)
H4	0.4799	0.0352	0.7859	0.034*
C5	0.3494 (2)	0.02600 (13)	0.5871 (5)	0.0300 (6)
C6	0.3051 (2)	0.05052 (12)	0.4044 (4)	0.0286 (6)
H6	0.2382	0.0327	0.3488	0.034*
C7	0.3631 (2)	0.10222 (12)	0.3065 (4)	0.0249 (5)
C8	0.4063 (2)	0.18286 (12)	0.0785 (4)	0.0244 (5)
C9	0.6138 (2)	0.13299 (14)	0.6532 (4)	0.0326 (6)
H9A	0.5976	0.1742	0.7350	0.049*
H9B	0.6653	0.1447	0.5413	0.049*
H9C	0.6472	0.0980	0.7428	0.049*
C10	0.2906 (2)	−0.02817 (14)	0.7122 (6)	0.0449 (7)
H10A	0.2119	−0.0282	0.6764	0.067*
H10B	0.2992	−0.0182	0.8603	0.067*
H10C	0.3225	−0.0733	0.6814	0.067*
C11	0.3837 (2)	0.22527 (13)	−0.1055 (4)	0.0290 (6)
H11A	0.3762	0.1956	−0.2275	0.043*
H11B	0.4449	0.2575	−0.1271	0.043*
H11C	0.3149	0.2510	−0.0846	0.043*
C12	0.5641 (2)	0.29687 (12)	0.4160 (4)	0.0246 (6)
C13	0.6479 (2)	0.31154 (13)	0.5558 (4)	0.0286 (6)
H13	0.7185	0.2908	0.5399	0.034*
C14	0.6288 (2)	0.35637 (12)	0.7187 (5)	0.0289 (6)
H14	0.6851	0.3657	0.8175	0.035*
C15	0.5266 (2)	0.38710 (13)	0.7346 (4)	0.0279 (6)
C16	0.4426 (2)	0.37384 (13)	0.5940 (5)	0.0306 (6)
H16	0.3728	0.3958	0.6080	0.037*
C17	0.4610 (2)	0.32882 (13)	0.4347 (5)	0.0299 (6)
H17	0.4041	0.3193	0.3373	0.036*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.05193 (19)	0.04310 (18)	0.04315 (19)	0.00241 (13)	0.00636 (14)	−0.01494 (17)
S1	0.0258 (3)	0.0285 (3)	0.0242 (3)	−0.0055 (2)	0.0024 (3)	0.0003 (3)
O1	0.0254 (9)	0.0279 (9)	0.0280 (10)	−0.0048 (8)	−0.0047 (8)	0.0031 (7)
O2	0.0234 (9)	0.0374 (10)	0.0401 (12)	−0.0016 (8)	0.0040 (8)	−0.0042 (8)
C1	0.0229 (12)	0.0234 (12)	0.0232 (14)	−0.0018 (9)	0.0018 (10)	−0.0029 (11)
C2	0.0216 (11)	0.0222 (12)	0.0216 (12)	0.0010 (10)	0.0030 (11)	−0.0001 (10)
C3	0.0229 (13)	0.0268 (14)	0.0234 (14)	0.0040 (9)	0.0016 (10)	0.0001 (11)
C4	0.0285 (13)	0.0277 (13)	0.0277 (16)	0.0068 (10)	−0.0001 (12)	0.0049 (10)
C5	0.0267 (13)	0.0230 (12)	0.0404 (16)	0.0036 (11)	0.0075 (12)	0.0047 (12)
C6	0.0218 (11)	0.0246 (12)	0.0395 (18)	0.0004 (9)	0.0007 (11)	0.0017 (11)
C7	0.0257 (12)	0.0244 (12)	0.0245 (14)	0.0041 (10)	−0.0008 (10)	0.0001 (10)
C8	0.0253 (12)	0.0246 (12)	0.0233 (13)	−0.0021 (10)	0.0010 (11)	−0.0020 (10)
C9	0.0289 (13)	0.0396 (14)	0.0293 (16)	0.0010 (12)	−0.0054 (12)	0.0023 (12)
C10	0.0357 (15)	0.0394 (15)	0.060 (2)	0.0003 (12)	0.0032 (17)	0.0258 (16)
C11	0.0296 (13)	0.0332 (13)	0.0241 (14)	0.0005 (11)	−0.0020 (11)	0.0012 (11)
C12	0.0255 (12)	0.0219 (12)	0.0264 (15)	−0.0037 (9)	−0.0003 (10)	0.0040 (10)
C13	0.0239 (13)	0.0287 (13)	0.0331 (15)	−0.0002 (11)	−0.0022 (11)	0.0003 (11)
C14	0.0261 (13)	0.0315 (13)	0.0293 (14)	−0.0018 (10)	−0.0050 (13)	0.0006 (12)
C15	0.0355 (13)	0.0219 (12)	0.0262 (15)	−0.0044 (10)	0.0030 (12)	−0.0001 (11)
C16	0.0258 (13)	0.0277 (14)	0.0382 (16)	0.0026 (11)	0.0022 (12)	0.0032 (12)
C17	0.0272 (12)	0.0281 (13)	0.0346 (15)	−0.0017 (11)	−0.0083 (14)	0.0042 (12)

Geometric parameters (Å, º) top

Br1—C15	1.894 (3)	C9—H9A	0.9800
S1—O2	1.4935 (18)	C9—H9B	0.9800
S1—C1	1.761 (2)	C9—H9C	0.9800
S1—C12	1.789 (3)	C10—H10A	0.9800
O1—C8	1.373 (3)	C10—H10B	0.9800
O1—C7	1.390 (3)	C10—H10C	0.9800
C1—C8	1.360 (4)	C11—H11A	0.9800
C1—C2	1.459 (4)	C11—H11B	0.9800
C2—C7	1.390 (4)	C11—H11C	0.9800
C2—C3	1.403 (4)	C12—C13	1.386 (3)
C3—C4	1.386 (4)	C12—C17	1.398 (4)
C3—C9	1.513 (3)	C13—C14	1.385 (4)
C4—C5	1.412 (4)	C13—H13	0.9500
C4—H4	0.9500	C14—C15	1.377 (4)
C5—C6	1.380 (4)	C14—H14	0.9500
C5—C10	1.506 (4)	C15—C16	1.386 (4)
C6—C7	1.380 (3)	C16—C17	1.369 (4)
C6—H6	0.9500	C16—H16	0.9500
C8—C11	1.471 (4)	C17—H17	0.9500

O2—S1—C1	110.48 (11)	H9A—C9—H9C	109.5
O2—S1—C12	106.92 (11)	H9B—C9—H9C	109.5
C1—S1—C12	98.85 (12)	C5—C10—H10A	109.5
C8—O1—C7	106.43 (19)	C5—C10—H10B	109.5
C8—C1—C2	107.6 (2)	H10A—C10—H10B	109.5
C8—C1—S1	118.3 (2)	C5—C10—H10C	109.5
C2—C1—S1	134.1 (2)	H10A—C10—H10C	109.5
C7—C2—C3	118.4 (2)	H10B—C10—H10C	109.5
C7—C2—C1	104.2 (2)	C8—C11—H11A	109.5
C3—C2—C1	137.3 (2)	C8—C11—H11B	109.5
C4—C3—C2	116.8 (2)	H11A—C11—H11B	109.5
C4—C3—C9	120.2 (3)	C8—C11—H11C	109.5
C2—C3—C9	122.9 (2)	H11A—C11—H11C	109.5
C3—C4—C5	123.5 (2)	H11B—C11—H11C	109.5
C3—C4—H4	118.3	C13—C12—C17	120.3 (2)
C5—C4—H4	118.3	C13—C12—S1	118.47 (19)
C6—C5—C4	119.5 (2)	C17—C12—S1	120.92 (19)
C6—C5—C10	121.1 (3)	C14—C13—C12	120.1 (2)
C4—C5—C10	119.4 (3)	C14—C13—H13	119.9
C7—C6—C5	116.5 (2)	C12—C13—H13	119.9
C7—C6—H6	121.8	C15—C14—C13	118.7 (3)
C5—C6—H6	121.8	C15—C14—H14	120.7
C6—C7—O1	123.8 (2)	C13—C14—H14	120.7
C6—C7—C2	125.2 (2)	C14—C15—C16	121.9 (3)
O1—C7—C2	111.0 (2)	C14—C15—Br1	118.4 (2)
C1—C8—O1	110.8 (2)	C16—C15—Br1	119.7 (2)
C1—C8—C11	133.3 (2)	C17—C16—C15	119.4 (2)
O1—C8—C11	115.9 (2)	C17—C16—H16	120.3
C3—C9—H9A	109.5	C15—C16—H16	120.3
C3—C9—H9B	109.5	C16—C17—C12	119.6 (3)
H9A—C9—H9B	109.5	C16—C17—H17	120.2
C3—C9—H9C	109.5	C12—C17—H17	120.2

O2—S1—C1—C8	−136.6 (2)	C1—C2—C7—C6	−179.0 (2)
C12—S1—C1—C8	111.5 (2)	C3—C2—C7—O1	179.3 (2)
O2—S1—C1—C2	45.2 (3)	C1—C2—C7—O1	0.0 (3)
C12—S1—C1—C2	−66.7 (3)	C2—C1—C8—O1	−0.3 (3)
C8—C1—C2—C7	0.2 (3)	S1—C1—C8—O1	−179.02 (17)
S1—C1—C2—C7	178.6 (2)	C2—C1—C8—C11	176.7 (3)
C8—C1—C2—C3	−178.9 (3)	S1—C1—C8—C11	−2.0 (4)
S1—C1—C2—C3	−0.6 (5)	C7—O1—C8—C1	0.4 (3)
C7—C2—C3—C4	−0.3 (4)	C7—O1—C8—C11	−177.2 (2)
C1—C2—C3—C4	178.7 (3)	O2—S1—C12—C13	13.9 (2)
C7—C2—C3—C9	−179.3 (2)	C1—S1—C12—C13	128.6 (2)
C1—C2—C3—C9	−0.3 (5)	O2—S1—C12—C17	−172.8 (2)
C2—C3—C4—C5	−0.4 (4)	C1—S1—C12—C17	−58.1 (2)
C9—C3—C4—C5	178.6 (2)	C17—C12—C13—C14	2.0 (4)
C3—C4—C5—C6	1.1 (4)	S1—C12—C13—C14	175.40 (19)
C3—C4—C5—C10	−177.2 (3)	C12—C13—C14—C15	−1.8 (4)
C4—C5—C6—C7	−1.1 (4)	C13—C14—C15—C16	0.7 (4)
C10—C5—C6—C7	177.2 (2)	C13—C14—C15—Br1	179.7 (2)
C5—C6—C7—O1	−178.5 (2)	C14—C15—C16—C17	0.2 (4)
C5—C6—C7—C2	0.4 (4)	Br1—C15—C16—C17	−178.9 (2)
C8—O1—C7—C6	178.8 (2)	C15—C16—C17—C12	0.0 (4)
C8—O1—C7—C2	−0.2 (3)	C13—C12—C17—C16	−1.1 (4)
C3—C2—C7—C6	0.3 (4)	S1—C12—C17—C16	−174.3 (2)

Hydrogen-bond geometry (Å, º) top

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

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11C···O2ⁱ	0.98	2.59	3.343 (3)	134
C17—H17···O2ⁱ	0.95	2.56	3.432 (3)	153
C4—H4···Cgⁱⁱ	0.95	2.89	3.724 (3)	147
C11—H11A···Cgⁱⁱⁱ	0.98	2.98	3.917 (3)	161

Symmetry codes: (i) x−1/2, −y+1/2, z; (ii) −x+1, −y, z+1/2; (iii) x, y, z−1.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₅BrO₂S
M_r	363.26
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	173
a, b, c (Å)	12.0911 (3), 19.4713 (3), 6.4482 (1)
V (Å³)	1518.10 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.85
Crystal size (mm)	0.33 × 0.29 × 0.19

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.456, 0.611
No. of measured, independent and observed [I > 2σ(I)] reflections	8258, 3190, 2797
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.078, 1.03
No. of reflections	3190
No. of parameters	194
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.55
Absolute structure	Flack (1983), 1131 Friedel pairs
Absolute structure parameter	0.014 (12)

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

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

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11C···O2ⁱ	0.98	2.59	3.343 (3)	134.0
C17—H17···O2ⁱ	0.95	2.56	3.432 (3)	152.8
C4—H4···Cgⁱⁱ	0.95	2.89	3.724 (3)	146.7
C11—H11A···Cgⁱⁱⁱ	0.98	2.98	3.917 (3)	161.0

Symmetry codes: (i) x−1/2, −y+1/2, z; (ii) −x+1, −y, z+1/2; (iii) x, y, z−1.

Acknowledgements

This work was supported by the Blue-Bio Industry Regional Innovation Center (RIC08-06-07) at Dongeui University as an RIC program under the Ministry of Knowledge Economy and Busan City.

References

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