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

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

doi:10.1107/S160053681200027X

organic compounds

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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Page o374

doi:10.1107/S160053681200027X

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3-(3-Chlorophenylsulfinyl)-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 29 December 2011; accepted 4 January 2012; online 14 January 2012)

In the title compound, C₁₇H₁₅ClO₂S, the 3-chlorophenyl ring makes a dihedral angle of 71.46 (4)° with the mean plane of the benzofuran fragment. In the crystal, molecules are linked by weak C—H⋯O hydrogen bonds and a slipped π–π interaction between the 3-chlorophenyl rings of adjacent molecules [centroid–centroid distance = 3.630 (2) Å, interplanar distance = 3.375 (2) Å and slippage = 1.337 (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. (2010 ); Seo et al. (2011 ).

Experimental

Crystal data

C₁₇H₁₅ClO₂S
M_r = 318.80
Triclinic, $[P \overline 1]$
a = 6.7900 (2) Å
b = 8.1288 (3) Å
c = 14.6813 (5) Å
α = 76.763 (2)°
β = 84.145 (2)°
γ = 73.241 (2)°
V = 754.73 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.39 mm⁻¹
T = 173 K
0.28 × 0.25 × 0.21 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.675, T_max = 0.746
14017 measured reflections
3704 independent reflections
3182 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.105
S = 1.05
3704 reflections
193 parameters
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.42 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11B⋯O2ⁱ	0.98	2.30	3.249 (2)	163
Symmetry code: (i) x-1, y, z.

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/S160053681200027X/pv2502sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681200027X/pv2502Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681200027X/pv2502Isup3.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-chlorophenylsulfinyl) (Choi et al. , 2010) or 3-(3-fluorophenylsufinyl) (Seo et al. , 2011) 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 0.005 (1) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle between the 3-chlorophenyl ring and the mean plane of the benzofurn fragment is 71.46 (4)°. The crystal packing (Fig. 2) is stabilized by weak intermolecular C–H···O hydrogen bonds (Table 1). The crystal packing (Fig. 2) is further stabilized by a weak slipped π–π interaction between the 3-chlorophenyl rings of adjacent molecules, with a Cg···Cgⁱⁱ distance of 3.630 (2) Å and an interplanar distance of 3.375 (2) Å resulting in a slippage of 1.337 (2) Å (Cg is the centroid of the C12-C17 3-chlorophenyl 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. (2010); Seo et al. (2011).

Experimental top

77% 3-Chloroperoxybenzoic acid (269 mg, 1.3 mmol) was added in small portions to a stirred solution of 3-(3-chlorophenylsulfanyl)-2,4,6-trimethyl 1-benzofuran (333 mg, 1.1 mmol) in dichloromethane (40 mL) at 273 K. After being stirred at room temperature for 5 h, 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. 402–403 K; R_f = 0.53 (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 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 radius.
	Fig. 2. A view of the C—H···O and π–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: (i) x - 1, y, z; (ii) - x + 1, - y + 1, - z + 2; (iii) x + 1, y, z.]

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

Crystal data top

C₁₇H₁₅ClO₂S	Z = 2
M_r = 318.80	F(000) = 332
Triclinic, P1	D_x = 1.403 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.7900 (2) Å	Cell parameters from 6373 reflections
b = 8.1288 (3) Å	θ = 2.7–28.1°
c = 14.6813 (5) Å	µ = 0.39 mm⁻¹
α = 76.763 (2)°	T = 173 K
β = 84.145 (2)°	Block, colourless
γ = 73.241 (2)°	0.28 × 0.25 × 0.21 mm
V = 754.73 (4) Å³

Data collection top

Bruker SMART APEXII CCD diffractometer	3704 independent reflections
Radiation source: rotating anode	3182 reflections with I > 2σ(I)
Graphite multilayer monochromator	R_int = 0.030
Detector resolution: 10.0 pixels mm^-1	θ_max = 28.3°, θ_min = 1.4°
ϕ and ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −10→10
T_min = 0.675, T_max = 0.746	l = −19→19
14017 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)] = 0.037	Hydrogen site location: difference Fourier map
wR(F²) = 0.105	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0546P)² + 0.219P] where P = (F_o² + 2F_c²)/3
3704 reflections	(Δ/σ)_max = 0.001
193 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.42 e Å⁻³

Crystal data top

C₁₇H₁₅ClO₂S	γ = 73.241 (2)°
M_r = 318.80	V = 754.73 (4) Å³
Triclinic, P1	Z = 2
a = 6.7900 (2) Å	Mo Kα radiation
b = 8.1288 (3) Å	µ = 0.39 mm⁻¹
c = 14.6813 (5) Å	T = 173 K
α = 76.763 (2)°	0.28 × 0.25 × 0.21 mm
β = 84.145 (2)°

Data collection top

Bruker SMART APEXII CCD diffractometer	3704 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3182 reflections with I > 2σ(I)
T_min = 0.675, T_max = 0.746	R_int = 0.030
14017 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.105	H-atom parameters constrained
S = 1.05	Δρ_max = 0.33 e Å⁻³
3704 reflections	Δρ_min = −0.42 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
Cl1	0.98398 (6)	0.23182 (6)	0.99982 (3)	0.04624 (14)
S1	0.46056 (6)	0.83926 (5)	0.83535 (3)	0.03407 (12)
O1	0.14598 (16)	0.96772 (15)	0.61039 (8)	0.0363 (3)
O2	0.65568 (19)	0.88857 (16)	0.83626 (9)	0.0443 (3)
C1	0.3829 (2)	0.8720 (2)	0.72075 (11)	0.0312 (3)
C2	0.4775 (2)	0.80409 (19)	0.63819 (10)	0.0300 (3)
C3	0.6724 (2)	0.7063 (2)	0.61075 (11)	0.0336 (3)
C4	0.6909 (2)	0.6719 (2)	0.52105 (12)	0.0368 (3)
H4	0.8208	0.6054	0.5009	0.044*
C5	0.5309 (3)	0.7288 (2)	0.45904 (11)	0.0367 (3)
C6	0.3406 (3)	0.8309 (2)	0.48513 (11)	0.0375 (3)
H6	0.2289	0.8745	0.4442	0.045*
C7	0.3229 (2)	0.8653 (2)	0.57378 (11)	0.0325 (3)
C8	0.1876 (2)	0.9692 (2)	0.69925 (11)	0.0336 (3)
C9	0.8536 (3)	0.6437 (3)	0.67277 (13)	0.0448 (4)
H9A	0.8515	0.5309	0.7141	0.067*
H9B	0.8462	0.7303	0.7106	0.067*
H9C	0.9813	0.6291	0.6340	0.067*
C10	0.5634 (3)	0.6788 (3)	0.36442 (12)	0.0464 (4)
H10A	0.5396	0.5633	0.3706	0.070*
H10B	0.7047	0.6741	0.3408	0.070*
H10C	0.4667	0.7665	0.3205	0.070*
C11	0.0176 (3)	1.0752 (2)	0.75130 (13)	0.0432 (4)
H11A	0.0667	1.0788	0.8111	0.065*
H11B	−0.0972	1.0217	0.7630	0.065*
H11C	−0.0288	1.1950	0.7141	0.065*
C12	0.5290 (2)	0.6027 (2)	0.86348 (10)	0.0302 (3)
C13	0.7090 (2)	0.5182 (2)	0.91058 (10)	0.0317 (3)
H13	0.7954	0.5830	0.9234	0.038*
C14	0.7601 (2)	0.3376 (2)	0.93850 (11)	0.0326 (3)
C15	0.6376 (2)	0.2399 (2)	0.92032 (11)	0.0339 (3)
H15	0.6762	0.1155	0.9394	0.041*
C16	0.4574 (3)	0.3280 (2)	0.87360 (11)	0.0355 (3)
H16	0.3716	0.2629	0.8606	0.043*
C17	0.4002 (2)	0.5095 (2)	0.84550 (11)	0.0339 (3)
H17	0.2753	0.5690	0.8145	0.041*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0373 (2)	0.0353 (2)	0.0654 (3)	−0.00594 (17)	−0.00790 (18)	−0.01169 (19)
S1	0.0379 (2)	0.0264 (2)	0.0417 (2)	−0.00941 (16)	0.00082 (15)	−0.01471 (16)
O1	0.0268 (5)	0.0343 (6)	0.0432 (6)	−0.0021 (4)	0.0024 (4)	−0.0087 (5)
O2	0.0469 (7)	0.0333 (6)	0.0612 (8)	−0.0190 (5)	−0.0072 (6)	−0.0144 (6)
C1	0.0296 (7)	0.0248 (7)	0.0394 (8)	−0.0070 (6)	0.0034 (6)	−0.0094 (6)
C2	0.0298 (7)	0.0223 (7)	0.0373 (7)	−0.0073 (6)	0.0040 (6)	−0.0072 (6)
C3	0.0305 (7)	0.0252 (7)	0.0434 (8)	−0.0060 (6)	0.0043 (6)	−0.0085 (6)
C4	0.0348 (8)	0.0281 (8)	0.0443 (8)	−0.0054 (6)	0.0103 (6)	−0.0105 (6)
C5	0.0432 (9)	0.0302 (8)	0.0367 (8)	−0.0127 (7)	0.0082 (6)	−0.0083 (6)
C6	0.0379 (8)	0.0339 (9)	0.0378 (8)	−0.0083 (7)	−0.0003 (6)	−0.0043 (6)
C7	0.0286 (7)	0.0254 (7)	0.0401 (8)	−0.0048 (6)	0.0045 (6)	−0.0061 (6)
C8	0.0307 (7)	0.0277 (8)	0.0417 (8)	−0.0075 (6)	0.0055 (6)	−0.0094 (6)
C9	0.0308 (8)	0.0460 (10)	0.0539 (10)	0.0006 (7)	0.0003 (7)	−0.0179 (8)
C10	0.0565 (11)	0.0459 (11)	0.0392 (9)	−0.0175 (9)	0.0098 (8)	−0.0144 (8)
C11	0.0331 (8)	0.0382 (9)	0.0551 (10)	−0.0038 (7)	0.0090 (7)	−0.0161 (8)
C12	0.0358 (7)	0.0257 (7)	0.0325 (7)	−0.0109 (6)	0.0039 (6)	−0.0124 (6)
C13	0.0338 (7)	0.0301 (8)	0.0365 (8)	−0.0126 (6)	0.0022 (6)	−0.0139 (6)
C14	0.0315 (7)	0.0315 (8)	0.0360 (7)	−0.0069 (6)	0.0035 (6)	−0.0137 (6)
C15	0.0429 (8)	0.0262 (8)	0.0358 (7)	−0.0111 (6)	0.0057 (6)	−0.0139 (6)
C16	0.0432 (8)	0.0341 (8)	0.0381 (8)	−0.0196 (7)	0.0034 (6)	−0.0161 (6)
C17	0.0367 (8)	0.0353 (8)	0.0348 (7)	−0.0139 (7)	−0.0002 (6)	−0.0130 (6)

Geometric parameters (Å, º) top

Cl1—C14	1.7412 (16)	C9—H9A	0.9800
S1—O2	1.4928 (12)	C9—H9B	0.9800
S1—C1	1.7534 (16)	C9—H9C	0.9800
S1—C12	1.8009 (15)	C10—H10A	0.9800
O1—C8	1.3661 (19)	C10—H10B	0.9800
O1—C7	1.3863 (18)	C10—H10C	0.9800
C1—C8	1.360 (2)	C11—H11A	0.9800
C1—C2	1.459 (2)	C11—H11B	0.9800
C2—C7	1.389 (2)	C11—H11C	0.9800
C2—C3	1.406 (2)	C12—C13	1.384 (2)
C3—C4	1.394 (2)	C12—C17	1.389 (2)
C3—C9	1.502 (2)	C13—C14	1.380 (2)
C4—C5	1.393 (2)	C13—H13	0.9500
C4—H4	0.9500	C14—C15	1.384 (2)
C5—C6	1.390 (2)	C15—C16	1.386 (2)
C5—C10	1.513 (2)	C15—H15	0.9500
C6—C7	1.379 (2)	C16—C17	1.386 (2)
C6—H6	0.9500	C16—H16	0.9500
C8—C11	1.486 (2)	C17—H17	0.9500

O2—S1—C1	111.41 (7)	H9A—C9—H9C	109.5
O2—S1—C12	106.01 (7)	H9B—C9—H9C	109.5
C1—S1—C12	98.39 (7)	C5—C10—H10A	109.5
C8—O1—C7	106.59 (12)	C5—C10—H10B	109.5
C8—C1—C2	107.12 (14)	H10A—C10—H10B	109.5
C8—C1—S1	118.56 (12)	C5—C10—H10C	109.5
C2—C1—S1	134.08 (12)	H10A—C10—H10C	109.5
C7—C2—C3	118.49 (14)	H10B—C10—H10C	109.5
C7—C2—C1	104.44 (13)	C8—C11—H11A	109.5
C3—C2—C1	137.02 (14)	C8—C11—H11B	109.5
C4—C3—C2	116.22 (15)	H11A—C11—H11B	109.5
C4—C3—C9	121.02 (14)	C8—C11—H11C	109.5
C2—C3—C9	122.75 (14)	H11A—C11—H11C	109.5
C5—C4—C3	124.16 (15)	H11B—C11—H11C	109.5
C5—C4—H4	117.9	C13—C12—C17	121.25 (14)
C3—C4—H4	117.9	C13—C12—S1	116.72 (11)
C6—C5—C4	119.45 (15)	C17—C12—S1	121.85 (12)
C6—C5—C10	120.21 (16)	C14—C13—C12	118.42 (13)
C4—C5—C10	120.34 (15)	C14—C13—H13	120.8
C7—C6—C5	116.27 (15)	C12—C13—H13	120.8
C7—C6—H6	121.9	C13—C14—C15	121.98 (15)
C5—C6—H6	121.9	C13—C14—Cl1	118.34 (12)
C6—C7—O1	123.93 (14)	C15—C14—Cl1	119.67 (12)
C6—C7—C2	125.32 (14)	C14—C15—C16	118.42 (14)
O1—C7—C2	110.75 (13)	C14—C15—H15	120.8
C1—C8—O1	111.09 (13)	C16—C15—H15	120.8
C1—C8—C11	133.38 (16)	C17—C16—C15	121.11 (14)
O1—C8—C11	115.53 (14)	C17—C16—H16	119.4
C3—C9—H9A	109.5	C15—C16—H16	119.4
C3—C9—H9B	109.5	C16—C17—C12	118.80 (15)
H9A—C9—H9B	109.5	C16—C17—H17	120.6
C3—C9—H9C	109.5	C12—C17—H17	120.6

O2—S1—C1—C8	−127.62 (13)	C1—C2—C7—C6	−178.73 (15)
C12—S1—C1—C8	121.46 (13)	C3—C2—C7—O1	−176.29 (13)
O2—S1—C1—C2	58.83 (17)	C1—C2—C7—O1	1.51 (16)
C12—S1—C1—C2	−52.10 (16)	C2—C1—C8—O1	1.05 (17)
C8—C1—C2—C7	−1.54 (16)	S1—C1—C8—O1	−174.11 (10)
S1—C1—C2—C7	172.54 (13)	C2—C1—C8—C11	−177.87 (17)
C8—C1—C2—C3	175.63 (17)	S1—C1—C8—C11	7.0 (3)
S1—C1—C2—C3	−10.3 (3)	C7—O1—C8—C1	−0.11 (17)
C7—C2—C3—C4	−2.9 (2)	C7—O1—C8—C11	179.01 (13)
C1—C2—C3—C4	−179.79 (16)	O2—S1—C12—C13	22.00 (13)
C7—C2—C3—C9	176.05 (15)	C1—S1—C12—C13	137.22 (12)
C1—C2—C3—C9	−0.8 (3)	O2—S1—C12—C17	−162.87 (12)
C2—C3—C4—C5	0.4 (2)	C1—S1—C12—C17	−47.65 (13)
C9—C3—C4—C5	−178.61 (16)	C17—C12—C13—C14	0.9 (2)
C3—C4—C5—C6	1.9 (2)	S1—C12—C13—C14	176.04 (11)
C3—C4—C5—C10	−177.54 (15)	C12—C13—C14—C15	0.3 (2)
C4—C5—C6—C7	−1.5 (2)	C12—C13—C14—Cl1	−178.73 (11)
C10—C5—C6—C7	177.93 (14)	C13—C14—C15—C16	−0.8 (2)
C5—C6—C7—O1	178.59 (14)	Cl1—C14—C15—C16	178.26 (12)
C5—C6—C7—C2	−1.1 (2)	C14—C15—C16—C17	0.1 (2)
C8—O1—C7—C6	179.30 (15)	C15—C16—C17—C12	1.1 (2)
C8—O1—C7—C2	−0.93 (16)	C13—C12—C17—C16	−1.6 (2)
C3—C2—C7—C6	3.5 (2)	S1—C12—C17—C16	−176.51 (12)

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	3.249 (2)	163

Symmetry code: (i) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₅ClO₂S
M_r	318.80
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	6.7900 (2), 8.1288 (3), 14.6813 (5)
α, β, γ (°)	76.763 (2), 84.145 (2), 73.241 (2)
V (Å³)	754.73 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.39
Crystal size (mm)	0.28 × 0.25 × 0.21

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.675, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	14017, 3704, 3182
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.105, 1.05
No. of reflections	3704
No. of parameters	193
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.42

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	3.249 (2)	162.8

Symmetry code: (i) x−1, y, z.

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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