2,4,6,7-Tetra­methyl-3-phenyl­sulfinyl-1-benzofuran

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

doi:10.1107/S1600536808015031

organic compounds

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ISSN: 2056-9890

Volume 64| Part 6| June 2008| Page o1143

doi:10.1107/S1600536808015031

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2,4,6,7-Tetramethyl-3-phenylsulfinyl-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 11 April 2008; accepted 18 May 2008; online 24 May 2008)

In the title compound, C₁₈H₁₈O₂S, the O atom and the phenyl group of the phenylsulfinyl substituent lie on opposite sides of the planar benzofuran fragment. The phenyl ring is nearly perpendicular to the benzofuran system [88.56 (7)°] and is tilted slightly towards it. Molecules form pseudo-helices along the a axis. The crystal structure is stabilized by a C—H⋯π interaction between a methyl H atom and the phenyl ring of the phenylsulfinyl substituent, and by intra- and intermolecular C—H⋯O interactions.

Related literature

For details of the pharmacological properties of benzofuran compounds, see: Howlett et al. (1999 ); Ward (1997 ). For the structures of other benzofuran derivatives, see: Choi et al. (2007 , 2008 ).

Experimental

Crystal data

C₁₈H₁₈O₂S
M_r = 298.38
Orthorhombic, P n a 2₁
a = 12.0402 (6) Å
b = 19.673 (1) Å
c = 6.4399 (3) Å
V = 1525.40 (13) Å³
Z = 4
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 173 (2) K
0.40 × 0.40 × 0.30 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: none
9082 measured reflections
2486 independent reflections
2339 reflections with I > 2σ(I)
R_int = 0.102

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.138
S = 1.08
2486 reflections
194 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.51 e Å⁻³
Δρ_min = −0.43 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17A⋯Cgⁱ	0.98	2.68	3.565 (5)	151
C10—H10⋯O2ⁱ	0.95	2.48	3.306 (4)	146
C15—H15B⋯O2	0.98	2.38	3.248 (4)	147
Symmetry code: (i) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z]$ . Cg is the centroid of the C9–C14 phenyl ring.

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); 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/S1600536808015031/fl2196sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808015031/fl2196Isup2.hkl

checkCIF report

Comment top

Benzofuran ring systems have attracted considerable interest because of their various pharmacological properties (Howlett et al., 1999; Ward, 1997). This work is related to earlier communications on the synthesis and structure of similar benzofuran analogues (Choi et al., 2007, 2008)

In the title commmpound, the benzofuran unit is essentially planar, with a mean deviation of 0.008 Å from the least-squares plane defined by the nine constituent atoms (Fig. 1). The phenyl ring (C9-C14) is almost perpendicular to the plane of the benzofuran system [88.56 (7)°] and is tilted slightly towards it.

The title commpound crystallized in the non-centrosymmetric space group Pna21 in spite of having no asymmetric carbon atoms. The space group was caused by a right handed pseudo-helix along the a axis. In addition, the molecular packing (Fig. 2) is stabilized by a C—H···π interaction between a methyl H atom and the phenyl ring of the phenylsulfinyl substituent, with a C17—17A···Cgⁱ separation of 3.565 (5) Å (Fig. 2 and Table1; Cg is the centroid of C9-C14 phenyl ring). The molecular packing is further stabilized by intra- and intermolecular C—H···O interactions (Fig. 2 and Table 1: symmetry code as in Fig. 2).

Related literature top

For details of the pharmacological properties of benzofuran compounds, see: Howlett et al. (1999); Ward (1997). For the structures of other benzofuran derivatives, see: Choi et al. (2007, 2008). Cg is the centroid of the C9–C14 phenyl ring.

Experimental top

3-Chloroperoxybenzoic acid (77%, 190 mg, 0.85 mmol) was added in small portions to a stirred solution of 2,4,6,7-tetramethyl-3-phenylsulfanyl-1-benzofuran (226 mg, 0.8 mmol) in dichloromethane (20 ml) at 273 K. After being stirred at room temperature for 2h, the mixture was washed with a saturated soution of sodium bicarbonate and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated in vacuum. The residue was purified by column chromatography (hexane-ethyl acetate, 2:1 v/v) to afford the title compound as a colorless solid [yield 80%, m.p. 407-408 K; R_f = 0.54 (hexane-ethyl acetate, 2:1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation from acetone at room temperature. Spectroscopic analysis: ¹H NMR (CDCl₃, 400 MHz) δ 2.13 (s, 3H), 2.29 (s, 3H), 2.37 (s, 3H), 2.71 (s, 3H), 6.77 (s, 1H), 7.39-7.45 (m, 3H), 7.48-7.51 (m, 2H); EI-MS 298 [M⁺].

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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, showing displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. View of the structure projected on the ab plane. C—H···π and C—H···O interactions are shown as dotted lines. Cg denotes the ring centroid. [Symmetry code: (i)x-1/2, -y+3/2, z; (ii) x+1/2, -y+3/2, z; (iii) -x+1, -y+1, z+1/2; (iv) -x+3/2, y-1/2, z-1/2; (iv) -x+1/2, y-1/2, z+1/2.]

2,4,6,7-Tetramethyl-3-phenylsulfinyl-1-benzofuran top

Crystal data top

C₁₈H₁₈O₂S	F(000) = 632
M_r = 298.38	D_x = 1.299 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: p_2c_-2n	Cell parameters from 5414 reflections
a = 12.0402 (6) Å	θ = 2.7–28.2°
b = 19.673 (1) Å	µ = 0.21 mm⁻¹
c = 6.4399 (3) Å	T = 173 K
V = 1525.40 (13) Å³	Block, colorless
Z = 4	0.40 × 0.40 × 0.30 mm

Data collection top

Bruker SMART CCD diffractometer	2339 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.102
Graphite monochromator	θ_max = 27.0°, θ_min = 2.7°
Detector resolution: 10.0 pixels mm^-1	h = −14→15
ϕ and ω scans	k = −25→24
9082 measured reflections	l = −8→4
2486 independent 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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.138	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0864P)² + 0.5202P] where P = (F_o² + 2F_c²)/3
2486 reflections	(Δ/σ)_max < 0.001
194 parameters	Δρ_max = 0.51 e Å⁻³
1 restraint	Δρ_min = −0.43 e Å⁻³

Crystal data top

C₁₈H₁₈O₂S	V = 1525.40 (13) Å³
M_r = 298.38	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 12.0402 (6) Å	µ = 0.21 mm⁻¹
b = 19.673 (1) Å	T = 173 K
c = 6.4399 (3) Å	0.40 × 0.40 × 0.30 mm

Data collection top

Bruker SMART CCD diffractometer	2339 reflections with I > 2σ(I)
9082 measured reflections	R_int = 0.102
2486 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	1 restraint
wR(F²) = 0.138	H-atom parameters constrained
S = 1.09	Δρ_max = 0.51 e Å⁻³
2486 reflections	Δρ_min = −0.43 e Å⁻³
194 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
S	0.60317 (5)	0.74039 (3)	0.74685 (15)	0.0220 (2)
O1	0.33116 (17)	0.63540 (10)	0.8280 (4)	0.0229 (5)
O2	0.71121 (16)	0.70681 (11)	0.6963 (4)	0.0308 (6)
C1	0.4924 (2)	0.68198 (13)	0.7252 (5)	0.0200 (6)
C2	0.4634 (2)	0.63018 (13)	0.5731 (5)	0.0199 (6)
C3	0.5073 (3)	0.60387 (14)	0.3879 (6)	0.0237 (6)
C4	0.4461 (3)	0.55262 (15)	0.2916 (5)	0.0274 (7)
H4	0.4744	0.5336	0.1668	0.033*
C5	0.3448 (3)	0.52741 (14)	0.3689 (6)	0.0277 (7)
C6	0.3011 (2)	0.55259 (14)	0.5539 (6)	0.0245 (7)
C7	0.3638 (2)	0.60360 (14)	0.6471 (5)	0.0207 (6)
C8	0.4118 (2)	0.68331 (14)	0.8720 (5)	0.0205 (6)
C9	0.5685 (2)	0.79514 (14)	0.5322 (5)	0.0204 (6)
C10	0.4647 (3)	0.82691 (15)	0.5279 (6)	0.0274 (7)
H10	0.4101	0.8171	0.6300	0.033*
C11	0.4437 (3)	0.87313 (16)	0.3706 (7)	0.0339 (8)
H11	0.3734	0.8950	0.3640	0.041*
C12	0.5237 (3)	0.88799 (16)	0.2224 (7)	0.0344 (8)
H12	0.5081	0.9202	0.1163	0.041*
C13	0.6266 (3)	0.85595 (15)	0.2287 (7)	0.0290 (7)
H13	0.6811	0.8658	0.1264	0.035*
C14	0.6494 (2)	0.80925 (14)	0.3858 (6)	0.0235 (7)
H14	0.7196	0.7874	0.3923	0.028*
C15	0.6131 (3)	0.62939 (17)	0.2903 (6)	0.0281 (8)
H15A	0.6436	0.5943	0.1986	0.042*
H15B	0.6672	0.6400	0.3994	0.042*
H15C	0.5975	0.6705	0.2095	0.042*
C16	0.2833 (3)	0.47364 (15)	0.2454 (9)	0.0399 (9)
H16A	0.2898	0.4297	0.3160	0.060*
H16B	0.3156	0.4703	0.1061	0.060*
H16C	0.2047	0.4862	0.2344	0.060*
C17	0.1937 (3)	0.52894 (17)	0.6488 (7)	0.0337 (8)
H17A	0.1314	0.5521	0.5812	0.051*
H17B	0.1935	0.5396	0.7975	0.051*
H17C	0.1862	0.4797	0.6296	0.051*
C18	0.3902 (3)	0.72565 (17)	1.0569 (6)	0.0270 (7)
H18A	0.4556	0.7536	1.0868	0.041*
H18B	0.3743	0.6963	1.1761	0.041*
H18C	0.3262	0.7552	1.0304	0.041*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S	0.0194 (3)	0.0245 (3)	0.0222 (4)	−0.0027 (2)	−0.0002 (3)	−0.0011 (4)
O1	0.0215 (10)	0.0254 (10)	0.0219 (12)	−0.0032 (8)	0.0032 (9)	0.0003 (9)
O2	0.0200 (10)	0.0354 (11)	0.0369 (16)	0.0011 (8)	−0.0010 (10)	0.0046 (10)
C1	0.0186 (12)	0.0206 (12)	0.0208 (17)	−0.0016 (9)	−0.0004 (12)	0.0020 (13)
C2	0.0207 (14)	0.0170 (12)	0.0219 (16)	0.0013 (10)	−0.0010 (13)	0.0037 (12)
C3	0.0248 (14)	0.0217 (14)	0.0245 (17)	0.0062 (10)	0.0002 (13)	0.0007 (13)
C4	0.0332 (16)	0.0252 (14)	0.0239 (19)	0.0066 (11)	−0.0020 (14)	−0.0058 (12)
C5	0.0322 (17)	0.0164 (12)	0.034 (2)	0.0029 (11)	−0.0089 (15)	−0.0041 (14)
C6	0.0234 (14)	0.0177 (12)	0.0323 (19)	0.0013 (10)	−0.0036 (14)	0.0047 (13)
C7	0.0201 (12)	0.0185 (12)	0.0234 (17)	0.0022 (10)	0.0002 (13)	0.0037 (12)
C8	0.0194 (13)	0.0212 (13)	0.0210 (16)	−0.0017 (10)	0.0018 (13)	0.0036 (12)
C9	0.0205 (13)	0.0170 (13)	0.0237 (16)	0.0009 (10)	−0.0002 (12)	−0.0011 (12)
C10	0.0232 (15)	0.0250 (14)	0.0340 (19)	−0.0003 (11)	0.0061 (14)	−0.0015 (13)
C11	0.0251 (16)	0.0282 (16)	0.048 (2)	0.0039 (11)	0.0034 (16)	0.0082 (16)
C12	0.0428 (18)	0.0261 (14)	0.034 (2)	−0.0007 (12)	0.0011 (17)	0.0064 (16)
C13	0.0305 (15)	0.0271 (14)	0.029 (2)	−0.0045 (11)	0.0062 (17)	0.0021 (16)
C14	0.0204 (14)	0.0217 (12)	0.0282 (18)	0.0002 (10)	0.0054 (13)	−0.0048 (13)
C15	0.0266 (15)	0.0333 (15)	0.025 (2)	0.0041 (11)	0.0058 (14)	−0.0023 (13)
C16	0.0422 (18)	0.0277 (15)	0.050 (2)	−0.0004 (12)	−0.007 (2)	−0.012 (2)
C17	0.0294 (16)	0.0307 (16)	0.041 (2)	−0.0080 (12)	−0.0016 (16)	0.0059 (16)
C18	0.0251 (16)	0.0323 (15)	0.0236 (18)	−0.0001 (12)	0.0020 (14)	−0.0031 (14)

Geometric parameters (Å, º) top

S—O2	1.495 (2)	C10—H10	0.9500
S—C1	1.766 (3)	C11—C12	1.387 (5)
S—C9	1.801 (3)	C11—H11	0.9500
O1—C7	1.379 (4)	C12—C13	1.391 (5)
O1—C8	1.383 (3)	C12—H12	0.9500
C1—C8	1.355 (4)	C13—C14	1.394 (5)
C1—C2	1.456 (4)	C13—H13	0.9500
C2—C7	1.393 (4)	C14—H14	0.9500
C2—C3	1.403 (5)	C15—H15A	0.9800
C3—C4	1.394 (4)	C15—H15B	0.9800
C3—C15	1.507 (4)	C15—H15C	0.9800
C4—C5	1.408 (5)	C16—H16A	0.9800
C4—H4	0.9500	C16—H16B	0.9800
C5—C6	1.393 (5)	C16—H16C	0.9800
C5—C16	1.516 (5)	C17—H17A	0.9800
C6—C7	1.392 (4)	C17—H17B	0.9800
C6—C17	1.504 (5)	C17—H17C	0.9800
C8—C18	1.476 (5)	C18—H18A	0.9800
C9—C14	1.383 (5)	C18—H18B	0.9800
C9—C10	1.398 (4)	C18—H18C	0.9800
C10—C11	1.385 (5)

O2—S—C1	110.63 (13)	C10—C11—H11	119.5
O2—S—C9	107.37 (15)	C12—C11—H11	119.5
C1—S—C9	98.84 (14)	C11—C12—C13	120.2 (3)
C7—O1—C8	106.4 (2)	C11—C12—H12	119.9
C8—C1—C2	108.1 (2)	C13—C12—H12	119.9
C8—C1—S	118.2 (2)	C12—C13—C14	119.7 (3)
C2—C1—S	133.6 (2)	C12—C13—H13	120.2
C7—C2—C3	118.5 (3)	C14—C13—H13	120.2
C7—C2—C1	103.8 (3)	C9—C14—C13	119.2 (3)
C3—C2—C1	137.7 (3)	C9—C14—H14	120.4
C4—C3—C2	116.5 (3)	C13—C14—H14	120.4
C4—C3—C15	120.1 (3)	C3—C15—H15A	109.5
C2—C3—C15	123.4 (3)	C3—C15—H15B	109.5
C3—C4—C5	123.7 (3)	H15A—C15—H15B	109.5
C3—C4—H4	118.1	C3—C15—H15C	109.5
C5—C4—H4	118.1	H15A—C15—H15C	109.5
C6—C5—C4	120.3 (3)	H15B—C15—H15C	109.5
C6—C5—C16	120.8 (3)	C5—C16—H16A	109.5
C4—C5—C16	118.9 (3)	C5—C16—H16B	109.5
C7—C6—C5	114.9 (3)	H16A—C16—H16B	109.5
C7—C6—C17	120.9 (3)	C5—C16—H16C	109.5
C5—C6—C17	124.2 (3)	H16A—C16—H16C	109.5
O1—C7—C6	122.5 (3)	H16B—C16—H16C	109.5
O1—C7—C2	111.3 (3)	C6—C17—H17A	109.5
C6—C7—C2	126.2 (3)	C6—C17—H17B	109.5
C1—C8—O1	110.3 (3)	H17A—C17—H17B	109.5
C1—C8—C18	134.4 (3)	C6—C17—H17C	109.5
O1—C8—C18	115.2 (3)	H17A—C17—H17C	109.5
C14—C9—C10	121.7 (3)	H17B—C17—H17C	109.5
C14—C9—S	118.7 (2)	C8—C18—H18A	109.5
C10—C9—S	119.3 (3)	C8—C18—H18B	109.5
C11—C10—C9	118.1 (3)	H18A—C18—H18B	109.5
C11—C10—H10	120.9	C8—C18—H18C	109.5
C9—C10—H10	120.9	H18A—C18—H18C	109.5
C10—C11—C12	121.0 (3)	H18B—C18—H18C	109.5

O2—S—C1—C8	138.4 (2)	C5—C6—C7—C2	−0.3 (4)
C9—S—C1—C8	−109.2 (3)	C17—C6—C7—C2	−179.2 (3)
O2—S—C1—C2	−43.7 (3)	C3—C2—C7—O1	−179.1 (2)
C9—S—C1—C2	68.7 (3)	C1—C2—C7—O1	0.4 (3)
C8—C1—C2—C7	−0.5 (3)	C3—C2—C7—C6	−0.4 (5)
S—C1—C2—C7	−178.5 (2)	C1—C2—C7—C6	179.2 (3)
C8—C1—C2—C3	179.0 (3)	C2—C1—C8—O1	0.3 (3)
S—C1—C2—C3	0.9 (6)	S—C1—C8—O1	178.72 (19)
C7—C2—C3—C4	0.2 (4)	C2—C1—C8—C18	−176.4 (3)
C1—C2—C3—C4	−179.2 (3)	S—C1—C8—C18	2.0 (5)
C7—C2—C3—C15	178.8 (3)	C7—O1—C8—C1	0.0 (3)
C1—C2—C3—C15	−0.6 (6)	C7—O1—C8—C18	177.4 (3)
C2—C3—C4—C5	0.6 (5)	O2—S—C9—C14	−13.1 (3)
C15—C3—C4—C5	−178.0 (3)	C1—S—C9—C14	−128.1 (3)
C3—C4—C5—C6	−1.4 (5)	O2—S—C9—C10	172.6 (2)
C3—C4—C5—C16	177.4 (3)	C1—S—C9—C10	57.6 (3)
C4—C5—C6—C7	1.2 (4)	C14—C9—C10—C11	0.5 (5)
C16—C5—C6—C7	−177.6 (3)	S—C9—C10—C11	174.7 (3)
C4—C5—C6—C17	−180.0 (3)	C9—C10—C11—C12	−0.6 (5)
C16—C5—C6—C17	1.3 (5)	C10—C11—C12—C13	0.6 (6)
C8—O1—C7—C6	−179.1 (3)	C11—C12—C13—C14	−0.6 (5)
C8—O1—C7—C2	−0.3 (3)	C10—C9—C14—C13	−0.5 (5)
C5—C6—C7—O1	178.3 (3)	S—C9—C14—C13	−174.7 (2)
C17—C6—C7—O1	−0.6 (5)	C12—C13—C14—C9	0.6 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17A···Cgⁱ	0.98	2.68	3.565 (5)	151
C10—H10···O2ⁱ	0.95	2.48	3.306 (4)	146
C15—H15B···O2	0.98	2.38	3.248 (4)	147

Symmetry code: (i) x−1/2, −y+3/2, z.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₈O₂S
M_r	298.38
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	173
a, b, c (Å)	12.0402 (6), 19.673 (1), 6.4399 (3)
V (Å³)	1525.40 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.40 × 0.40 × 0.30

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	9082, 2486, 2339
R_int	0.102
(sin θ/λ)_max (Å⁻¹)	0.638

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.138, 1.09
No. of reflections	2486
No. of parameters	194
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.51, −0.43

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), 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
C17—H17A···Cgⁱ	0.98	2.68	3.565 (5)	151.1
C10—H10···O2ⁱ	0.95	2.48	3.306 (4)	145.8
C15—H15B···O2	0.98	2.38	3.248 (4)	147.3

Symmetry code: (i) x−1/2, −y+3/2, z.

References

Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2001). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2007). Acta Cryst. E63, o4042. Web of Science CSD CrossRef IUCr Journals Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2008). Acta Cryst. E64, o486. Web of Science CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Howlett, D. R., Perry, A. E., Godfrey, F., Swatton, J. E., Jennings, K. H., Spitzfaden, C., Wadsworth, H., Wood, S. J. & Markwell, R. E. (1999). Biochem. J. 340, 283–289. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Ward, R. S. (1997). Nat. Prod. Rep. 14, 43–74. CrossRef CAS Web of Science Google Scholar

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Volume 64| Part 6| June 2008| Page o1143

doi:10.1107/S1600536808015031

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