2,5,7-Trimethyl-3-phenyl­sulfonyl-1-benzofuran

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

doi:10.1107/S1600536808008477

organic compounds

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ISSN: 2056-9890

Volume 64| Part 5| May 2008| Page o794

doi:10.1107/S1600536808008477

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2,5,7-Trimethyl-3-phenylsulfonyl-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 2008; accepted 29 March 2008; online 2 April 2008)

The title compound, C₁₇H₁₆O₃S, was prepared by the oxidation of 2,5,7-trimethyl-3-phenylsulfanyl-1-benzofuran with 3-chloroperoxybenzoic acid. The phenyl ring exhibits a dihedral angle of 81.16 (4)° with the plane of the benzofuran fragment. The crystal structure is stabilized by π–π interactions between the furan and benzene rings of neighbouring molecules [centroid–centroid distance = 3.874 (2) Å] and by C—H⋯π interactions between a phenyl H atom of the phenylsulfonyl substituent and the furan ring of adjacent molecules. In addition, the crystal structure exhibits intra- and intermolecular C—H⋯O interactions.

Related literature

For the crystal structures of similar substituted benzofuran compounds, see: Choi et al. (2007a ,b ).

Experimental

Crystal data

C₁₇H₁₆O₃S
M_r = 300.36
Monoclinic, P 2₁ /n
a = 9.2468 (7) Å
b = 8.4238 (7) Å
c = 18.963 (2) Å
β = 91.535 (2)°
V = 1476.6 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 173 (2) K
0.40 × 0.40 × 0.10 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: none
8704 measured reflections
3212 independent reflections
2544 reflections with I > 2σ(I)
R_int = 0.041

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.104
S = 1.03
3212 reflections
193 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯Cg1ⁱ	0.95	2.81	3.747 (3)	169
C16—H16C⋯O3ⁱⁱ	0.98	2.48	3.403 (2)	158
C17—H17A⋯O2	0.98	2.42	3.135 (3)	129
Symmetry codes: (i) -x+1, -y+2, -z; (ii) -x+2, -y+1, -z. Cg1 is the centroid of the O1/C8/C1/C2/C7 furan 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/S1600536808008477/zl2106sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808008477/zl2106Isup2.hkl

checkCIF report

Comment top

This work is related to earlier communications on the synthesis and structure of substituted benzofuran analogues, viz. 2,5-dimethyl-3-methylsulfinyl-1-benzofuran (Choi et al., 2007a) and 2,5-dimethyl-3-phenylsulfinyl-1-benzofuran (Choi et al., 2007b). Herein we report the molecular and crystal structure of the title compound, 2,5,7-trimethyl-3-phenylsulfonyl-1-benzofuran (Fig. 1).

The benzofuran unit is almost planar, with a mean deviation of 0.009 Å from the least-squares plane defined by the nine constituent atoms. The phenyl ring (C9—C14) is almost perpendicular to the plane of the benzofuran ring system [81.16 (4) °] and is tilted slightly towards it. The crystal packing (Fig. 2) is stabilized by aromatic π—π stacking interactions between the furan and the benzene rings from neighbouring molecules. The Cg1···Cg2ⁱⁱ distance is 3.874 (2)Å (Cg1 and Cg2 are the centroids of the O1/C8/C1/C2/C7 furan ring and the C2—C7 benzene ring, respectively, symmetry code as in Fig. 2). The molecular packing is further stabilized by C—H···π interactions between a phenyl H atom of the phenylsulfonyl substituent and the furan ring of the benzofuran unit, with a C12—H12···Cgⁱ separation of 2.81 Å (Fig. 2 and Table 1; Cg1 is the centroid of the O1/C8/C1/C2/C7 furan ring, symmetry code as in Fig. 2). Additionally, intra- and intermolecular C—H···O interactions in the structure were observed (Fig. 2 and Table 1; symmetry code as in Fig. 2).

Related literature top

For the crystal structures of similar substituted benzofuran compounds, see: Choi et al. (2007a,b).

Experimental top

3-Chloroperoxybenzoic acid (77%, 471 mg, 2.1 mmol) was added in small portions to a stirred solution of 2,5,7-trimethyl-3-phenylsulfanyl-1-benzofuran (268 mg, 1.0 mmol) in dichloromethane (30 ml) at 273 K. After being stirred for 4 h at room temperature, the mixture was washed with saturated sodium bicarbonate solution 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 81%, m.p. 399–400 K; R_f = 0.61 (hexane-ethyl acetate, 2:1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by evaporation of a solution of the title compound in benzene at room temperature. Spectroscopic analysis: ¹H NMR (CDCl₃, 400 MHz) δ 2.41 (s, 6H), 2.80 (s, 3H), 6.92 (s, 1H), 7.47–7.52 (m, 4H), 8.01 (d, J = 7.68 Hz, 2H); EI—MS 300 [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 ellipsoides drawn at the 50% probability level.
	Fig. 2. π—π, C—H···π and C—H···O interactions (dotted lines) in the title compound. Cg denotes the ring centroid. [Symmetry code: (i) -x + 1, -y + 2, -z; (ii) -x + 2, -y + 1, -z.]

2,5,7-Trimethyl-3-phenylsulfonyl-1-benzofuran top

Crystal data top

C₁₇H₁₆O₃S	F(000) = 632
M_r = 300.36	D_x = 1.351 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -p 2yn	Cell parameters from 4291 reflections
a = 9.2468 (7) Å	θ = 2.5–28.3°
b = 8.4238 (7) Å	µ = 0.23 mm⁻¹
c = 18.963 (2) Å	T = 173 K
β = 91.535 (2)°	Block, colorless
V = 1476.6 (2) Å³	0.40 × 0.40 × 0.10 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	2544 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.041
Graphite monochromator	θ_max = 27.0°, θ_min = 2.5°
Detector resolution: 10.0 pixels mm^-1	h = −11→11
ϕ and ω scans	k = −7→10
8704 measured reflections	l = −24→23
3212 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)] = 0.037	Hydrogen site location: difference Fourier map
wR(F²) = 0.104	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0467P)² + 0.6422P] where P = (F_o² + 2F_c²)/3
3212 reflections	(Δ/σ)_max < 0.001
193 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.38 e Å⁻³

Crystal data top

C₁₇H₁₆O₃S	V = 1476.6 (2) Å³
M_r = 300.36	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.2468 (7) Å	µ = 0.23 mm⁻¹
b = 8.4238 (7) Å	T = 173 K
c = 18.963 (2) Å	0.40 × 0.40 × 0.10 mm
β = 91.535 (2)°

Data collection top

Bruker SMART CCD diffractometer	2544 reflections with I > 2σ(I)
8704 measured reflections	R_int = 0.041
3212 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.104	H-atom parameters constrained
S = 1.04	Δρ_max = 0.30 e Å⁻³
3212 reflections	Δρ_min = −0.38 e Å⁻³
193 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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	0.71396 (5)	0.59940 (5)	0.11202 (2)	0.02746 (13)
O1	1.04792 (13)	0.77976 (15)	0.01610 (7)	0.0331 (3)
O2	0.77401 (15)	0.57958 (16)	0.18201 (6)	0.0386 (3)
O3	0.63915 (14)	0.46890 (14)	0.07823 (7)	0.0346 (3)
C1	0.84920 (18)	0.6601 (2)	0.05599 (9)	0.0270 (4)
C2	0.84265 (18)	0.6499 (2)	−0.02041 (9)	0.0260 (4)
C3	0.74772 (19)	0.5861 (2)	−0.07118 (9)	0.0290 (4)
H3	0.6625	0.5321	−0.0579	0.035*
C4	0.7809 (2)	0.6035 (2)	−0.14184 (9)	0.0330 (4)
C5	0.9071 (2)	0.6844 (2)	−0.16049 (10)	0.0346 (4)
H5	0.9266	0.6957	−0.2092	0.042*
C6	1.00483 (19)	0.7488 (2)	−0.11156 (10)	0.0328 (4)
C7	0.96763 (19)	0.7270 (2)	−0.04190 (9)	0.0291 (4)
C8	0.97377 (19)	0.7376 (2)	0.07465 (9)	0.0304 (4)
C9	0.59363 (18)	0.7624 (2)	0.11293 (9)	0.0263 (4)
C10	0.48964 (19)	0.7768 (2)	0.05910 (9)	0.0318 (4)
H10	0.4830	0.7005	0.0223	0.038*
C11	0.3956 (2)	0.9051 (2)	0.06032 (11)	0.0402 (5)
H11	0.3232	0.9165	0.0242	0.048*
C12	0.4063 (2)	1.0159 (2)	0.11345 (12)	0.0450 (5)
H12	0.3416	1.1035	0.1137	0.054*
C13	0.5111 (2)	1.0004 (2)	0.16670 (11)	0.0428 (5)
H13	0.5180	1.0776	0.2032	0.051*
C14	0.6058 (2)	0.8729 (2)	0.16692 (10)	0.0329 (4)
H14	0.6777	0.8615	0.2033	0.040*
C15	0.6791 (2)	0.5378 (3)	−0.19827 (10)	0.0461 (5)
H15A	0.6497	0.4301	−0.1853	0.069*
H15B	0.7282	0.5348	−0.2434	0.069*
H15C	0.5934	0.6058	−0.2027	0.069*
C16	1.1407 (2)	0.8345 (2)	−0.13129 (12)	0.0438 (5)
H16A	1.1486	0.9339	−0.1046	0.066*
H16B	1.1370	0.8581	−0.1819	0.066*
H16C	1.2249	0.7675	−0.1202	0.066*
C17	1.0431 (2)	0.7849 (2)	0.14286 (10)	0.0398 (5)
H17A	0.9787	0.7586	0.1814	0.060*
H17B	1.0614	0.8994	0.1427	0.060*
H17C	1.1348	0.7278	0.1495	0.060*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S	0.0317 (2)	0.0259 (2)	0.0248 (2)	0.00101 (17)	0.00055 (16)	0.00232 (17)
O1	0.0278 (6)	0.0313 (7)	0.0401 (7)	−0.0011 (5)	0.0010 (5)	−0.0019 (6)
O2	0.0440 (8)	0.0429 (8)	0.0287 (7)	0.0047 (6)	−0.0027 (6)	0.0058 (6)
O3	0.0403 (7)	0.0252 (6)	0.0383 (7)	−0.0040 (5)	0.0022 (6)	−0.0008 (5)
C1	0.0264 (8)	0.0274 (9)	0.0273 (8)	0.0029 (7)	−0.0003 (6)	−0.0001 (7)
C2	0.0276 (8)	0.0229 (8)	0.0276 (8)	0.0051 (7)	0.0019 (6)	0.0015 (7)
C3	0.0301 (9)	0.0280 (9)	0.0289 (9)	0.0026 (7)	0.0005 (7)	0.0000 (7)
C4	0.0383 (10)	0.0317 (9)	0.0289 (9)	0.0091 (8)	−0.0003 (7)	0.0010 (8)
C5	0.0430 (10)	0.0332 (10)	0.0281 (9)	0.0124 (8)	0.0082 (8)	0.0045 (8)
C6	0.0334 (10)	0.0260 (9)	0.0395 (10)	0.0081 (7)	0.0098 (8)	0.0050 (8)
C7	0.0287 (8)	0.0238 (8)	0.0348 (9)	0.0043 (7)	0.0007 (7)	−0.0003 (7)
C8	0.0294 (9)	0.0274 (9)	0.0343 (9)	0.0047 (7)	−0.0008 (7)	−0.0013 (7)
C9	0.0253 (8)	0.0252 (8)	0.0286 (8)	−0.0030 (7)	0.0045 (7)	0.0023 (7)
C10	0.0320 (9)	0.0308 (9)	0.0324 (9)	−0.0035 (7)	0.0006 (7)	0.0012 (8)
C11	0.0303 (10)	0.0424 (11)	0.0480 (12)	0.0021 (8)	0.0011 (8)	0.0113 (9)
C12	0.0404 (11)	0.0350 (11)	0.0605 (13)	0.0097 (9)	0.0177 (10)	0.0049 (10)
C13	0.0488 (12)	0.0338 (10)	0.0465 (12)	0.0003 (9)	0.0147 (9)	−0.0076 (9)
C14	0.0339 (9)	0.0345 (10)	0.0307 (9)	−0.0040 (8)	0.0066 (7)	−0.0033 (8)
C15	0.0492 (12)	0.0601 (14)	0.0285 (10)	0.0059 (11)	−0.0055 (8)	−0.0026 (9)
C16	0.0401 (11)	0.0361 (11)	0.0561 (13)	0.0031 (9)	0.0161 (10)	0.0097 (9)
C17	0.0359 (10)	0.0416 (11)	0.0413 (11)	0.0006 (9)	−0.0096 (8)	−0.0055 (9)

Geometric parameters (Å, º) top

S—O2	1.4346 (13)	C9—C10	1.389 (2)
S—O3	1.4401 (13)	C10—C11	1.388 (3)
S—C1	1.7394 (17)	C10—H10	0.9500
S—C9	1.7674 (17)	C11—C12	1.375 (3)
O1—C8	1.367 (2)	C11—H11	0.9500
O1—C7	1.384 (2)	C12—C13	1.387 (3)
C1—C8	1.363 (2)	C12—H12	0.9500
C1—C2	1.451 (2)	C13—C14	1.386 (3)
C2—C3	1.393 (2)	C13—H13	0.9500
C2—C7	1.396 (2)	C14—H14	0.9500
C3—C4	1.390 (2)	C15—H15A	0.9800
C3—H3	0.9500	C15—H15B	0.9800
C4—C5	1.405 (3)	C15—H15C	0.9800
C4—C15	1.511 (3)	C16—H16A	0.9800
C5—C6	1.388 (3)	C16—H16B	0.9800
C5—H5	0.9500	C16—H16C	0.9800
C6—C7	1.386 (2)	C17—H17A	0.9800
C6—C16	1.505 (3)	C17—H17B	0.9800
C8—C17	1.483 (2)	C17—H17C	0.9800
C9—C14	1.386 (2)

O2—S—O3	119.48 (8)	C11—C10—C9	118.54 (17)
O2—S—C1	109.43 (8)	C11—C10—H10	120.7
O3—S—C1	107.29 (8)	C9—C10—H10	120.7
O2—S—C9	108.03 (8)	C12—C11—C10	120.53 (19)
O3—S—C9	107.59 (8)	C12—C11—H11	119.7
C1—S—C9	103.94 (8)	C10—C11—H11	119.7
C8—O1—C7	106.96 (13)	C11—C12—C13	120.35 (19)
C8—C1—C2	107.46 (15)	C11—C12—H12	119.8
C8—C1—S	126.78 (14)	C13—C12—H12	119.8
C2—C1—S	125.53 (13)	C14—C13—C12	120.26 (19)
C3—C2—C7	119.27 (16)	C14—C13—H13	119.9
C3—C2—C1	136.18 (16)	C12—C13—H13	119.9
C7—C2—C1	104.55 (15)	C13—C14—C9	118.66 (18)
C4—C3—C2	118.31 (17)	C13—C14—H14	120.7
C4—C3—H3	120.8	C9—C14—H14	120.7
C2—C3—H3	120.8	C4—C15—H15A	109.5
C3—C4—C5	119.98 (17)	C4—C15—H15B	109.5
C3—C4—C15	119.65 (18)	H15A—C15—H15B	109.5
C5—C4—C15	120.36 (17)	C4—C15—H15C	109.5
C6—C5—C4	123.47 (17)	H15A—C15—H15C	109.5
C6—C5—H5	118.3	H15B—C15—H15C	109.5
C4—C5—H5	118.3	C6—C16—H16A	109.5
C7—C6—C5	114.32 (17)	C6—C16—H16B	109.5
C7—C6—C16	122.04 (18)	H16A—C16—H16B	109.5
C5—C6—C16	123.64 (17)	C6—C16—H16C	109.5
O1—C7—C6	124.99 (16)	H16A—C16—H16C	109.5
O1—C7—C2	110.38 (15)	H16B—C16—H16C	109.5
C6—C7—C2	124.63 (17)	C8—C17—H17A	109.5
C1—C8—O1	110.64 (15)	C8—C17—H17B	109.5
C1—C8—C17	134.26 (17)	H17A—C17—H17B	109.5
O1—C8—C17	115.10 (15)	C8—C17—H17C	109.5
C14—C9—C10	121.66 (17)	H17A—C17—H17C	109.5
C14—C9—S	119.35 (14)	H17B—C17—H17C	109.5
C10—C9—S	118.98 (13)

O2—S—C1—C8	−24.52 (19)	C3—C2—C7—O1	−179.24 (14)
O3—S—C1—C8	−155.54 (16)	C1—C2—C7—O1	0.79 (18)
C9—S—C1—C8	90.68 (17)	C3—C2—C7—C6	1.4 (3)
O2—S—C1—C2	161.63 (14)	C1—C2—C7—C6	−178.60 (16)
O3—S—C1—C2	30.61 (17)	C2—C1—C8—O1	0.6 (2)
C9—S—C1—C2	−83.18 (16)	S—C1—C8—O1	−174.20 (12)
C8—C1—C2—C3	179.23 (19)	C2—C1—C8—C17	−179.81 (19)
S—C1—C2—C3	−5.9 (3)	S—C1—C8—C17	5.4 (3)
C8—C1—C2—C7	−0.81 (19)	C7—O1—C8—C1	−0.07 (19)
S—C1—C2—C7	174.03 (13)	C7—O1—C8—C17	−179.78 (15)
C7—C2—C3—C4	−0.7 (2)	O2—S—C9—C14	20.07 (16)
C1—C2—C3—C4	179.30 (18)	O3—S—C9—C14	150.32 (14)
C2—C3—C4—C5	−0.3 (3)	C1—S—C9—C14	−96.11 (15)
C2—C3—C4—C15	−179.10 (17)	O2—S—C9—C10	−160.35 (13)
C3—C4—C5—C6	0.8 (3)	O3—S—C9—C10	−30.10 (15)
C15—C4—C5—C6	179.52 (17)	C1—S—C9—C10	83.47 (15)
C4—C5—C6—C7	−0.1 (3)	C14—C9—C10—C11	−0.5 (3)
C4—C5—C6—C16	179.55 (17)	S—C9—C10—C11	179.95 (13)
C8—O1—C7—C6	178.91 (16)	C9—C10—C11—C12	0.5 (3)
C8—O1—C7—C2	−0.48 (18)	C10—C11—C12—C13	−0.2 (3)
C5—C6—C7—O1	179.76 (15)	C11—C12—C13—C14	−0.1 (3)
C16—C6—C7—O1	0.1 (3)	C12—C13—C14—C9	0.2 (3)
C5—C6—C7—C2	−0.9 (3)	C10—C9—C14—C13	0.1 (3)
C16—C6—C7—C2	179.37 (16)	S—C9—C14—C13	179.70 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···Cg1ⁱ	0.95	2.81	3.747 (3)	169
C16—H16C···O3ⁱⁱ	0.98	2.48	3.403 (2)	158
C17—H17A···O2	0.98	2.42	3.135 (3)	129

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

Experimental details

Crystal data
Chemical formula	C₁₇H₁₆O₃S
M_r	300.36
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	173
a, b, c (Å)	9.2468 (7), 8.4238 (7), 18.963 (2)
β (°)	91.535 (2)
V (Å³)	1476.6 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.40 × 0.40 × 0.10

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	8704, 3212, 2544
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.104, 1.04
No. of reflections	3212
No. of parameters	193
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.38

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
C12—H12···Cg1ⁱ	0.95	2.81	3.747 (3)	168.7
C16—H16C···O3ⁱⁱ	0.98	2.48	3.403 (2)	157.9
C17—H17A···O2	0.98	2.42	3.135 (3)	129.4

Symmetry codes: (i) −x+1, −y+2, −z; (ii) −x+2, −y+1, −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. (2007a). Acta Cryst. E63, o1823–o1824. Web of Science CSD CrossRef IUCr Journals Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2007b). Acta Cryst. E63, o4042. Web of Science CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 64| Part 5| May 2008| Page o794

doi:10.1107/S1600536808008477

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