5-Ethyl-2-methyl-3-phenyl­sulfonyl-1-benzofuran

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

doi:10.1107/S1600536808012877

organic compounds

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ISSN: 2056-9890

Volume 64| Part 6| June 2008| Page o1016

doi:10.1107/S1600536808012877

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5-Ethyl-2-methyl-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 3 April 2008; accepted 1 May 2008; online 7 May 2008)

The title compound, C₁₇H₁₆O₃S, was prepared by the oxidation of 5-ethyl-2-methyl-3-phenylsulfanyl-1-benzofuran with 3-chloroperoxybenzoic acid. The phenyl ring makes a dihedral angle of 75.94 (8)° with the plane of the benzofuran fragment. The crystal structure is stabilized by π–π interactions between the furan rings of neighbouring molecules [centroid–centroid distance = 3.620 (4) Å]. In addition, the crystal structure exhibits C—H⋯π interactions.

Related literature

For the crystal structures of similar 3-phenylsulfonyl-1-benzofuran compounds, see: Choi et al. (2008a ,b ).

Experimental

Crystal data

C₁₇H₁₆O₃S
M_r = 300.36
Monoclinic, P 2₁ /n
a = 8.7009 (4) Å
b = 8.2019 (4) Å
c = 20.682 (1) Å
β = 97.301 (1)°
V = 1463.98 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 173 (2) K
0.40 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: none
8693 measured reflections
3194 independent reflections
2264 reflections with I > 2σ(I)
R_int = 0.048

Refinement

R[F² > 2σ(F²)] = 0.056
wR(F²) = 0.148
S = 1.03
3194 reflections
192 parameters
H-atom parameters constrained
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.49 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15C⋯Cg2ⁱ	0.98	2.80	3.592 (4)	139
C16—H16B⋯Cg2ⁱⁱ	0.98	3.21	3.903 (4)	128
Symmetry codes: (i) -x+1, -y+2, -z; (ii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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/S1600536808012877/cf2194sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808012877/cf2194Isup2.hkl

checkCIF report

Comment top

As a part of our ongoing studies on the synthesis and structure of 3-phenyl-sulfonyl-1-benzofuran analogues, the crystal structure of 5-bromo-2-methyl-3-phenylsulfonyl-1-benzofuran (Choi et al., 2008a) and 2,5,7-trimethyl-3-phenylsulfonyl-1-benzofuran (Choi et al., 2008b) have been described in the literature. Here we report the crystal structure of the title compound, 5-ethyl-2-methyl-3-phenylsulfonyl-1-benzofuran (Fig. 1).

The benzofuran unit is essentially planar, with a mean deviation of 0.007 Å from the least-squares plane defined by the nine constituent atoms. The phenyl ring (C9—C14) makes a dihedral angle of 75.94 (8)° with the plane of the benzofuran fragment. The crystal packing (Fig. 2) is stabilized by aromatic π-π stacking interactions between the furan rings of neighbouring molecules. The Cg1···Cg1ⁱ distance is 3.620 (4) Å (Cg1 is the centroid of the O1/C8/C1/C2/C7 furan ring, symmetry code as in Fig. 2). The molecular packing is further stabilized by C—H···π interactions (Table 1 and Fig. 2); one between a methyl H atom and the benzene ring of the benzofuran unit, i.e. C15—H15C···Cg2ⁱ, a second between a methylene H atom of the ethyl group and the benzene ring of the benzofuran unit, i.e. C16—H16B···Cg2ⁱⁱ, respectively. In both cases the benzene ring (Cg2) is involved (Cg2 is the centroid of the C2–7 benzene ring, symmetry code as in Fig. 2).

Related literature top

For the crystal structures of similar 3-phenylsulfonyl-1-benzofuran compounds, see: Choi et al. (2008a,b).

Experimental top

3-Chloroperoxybenzoic acid (77%, 471 mg, 2.1 mmol) was added in small portions to a stirred solution of 5-ethyl-2-methyl-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 80%, m.p. 396- 397 K; R_f = 0.66 (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 1.26 (t, J = 7.68 Hz, 3H), 2.74 (q, J = 7.72 Hz, 2H), 2.79 (s, 3H), 7.14 (d, J = 8.44 Hz and 1.48 Hz, 1H), 7.32 (d, J = 8.44 Hz, 1H), 7.48–7.61 (m, 3H), 7.69 (s, 1H), 8.01 (d, J = 6.96 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 ellipsoids drawn at the 50% probability level.
	Fig. 2. π—π and C—H···π interactions (dotted lines) in the title compound. Cg denotes the ring centroids. [Symmetry code: (i) -x + 1, -y + 2, -z: (ii) -x + 3/2, y + 1/2, -z + 1/2; (iii) -x + 3/2, y - 1/2, -z + 1/2.]

5-Ethyl-2-methyl-3-phenylsulfonyl-1-benzofuran top

Crystal data top

C₁₇H₁₆O₃S	F(000) = 632
M_r = 300.36	D_x = 1.363 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P_2yn	Cell parameters from 2779 reflections
a = 8.7009 (4) Å	θ = 2.4–27.9°
b = 8.2019 (4) Å	µ = 0.23 mm⁻¹
c = 20.682 (1) Å	T = 173 K
β = 97.301 (1)°	Block, colorless
V = 1463.98 (12) Å³	0.40 × 0.20 × 0.20 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	2264 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.048
Graphite monochromator	θ_max = 27.0°, θ_min = 2.4°
Detector resolution: 10.0 pixels mm^-1	h = −8→11
ϕ and ω scans	k = −8→10
8693 measured reflections	l = −24→26
3194 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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.148	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0725P)² + 0.989P] where P = (F_o² + 2F_c²)/3
3194 reflections	(Δ/σ)_max < 0.001
192 parameters	Δρ_max = 0.42 e Å⁻³
0 restraints	Δρ_min = −0.49 e Å⁻³

Crystal data top

C₁₇H₁₆O₃S	V = 1463.98 (12) Å³
M_r = 300.36	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.7009 (4) Å	µ = 0.23 mm⁻¹
b = 8.2019 (4) Å	T = 173 K
c = 20.682 (1) Å	0.40 × 0.20 × 0.20 mm
β = 97.301 (1)°

Data collection top

Bruker SMART CCD diffractometer	2264 reflections with I > 2σ(I)
8693 measured reflections	R_int = 0.048
3194 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	0 restraints
wR(F²) = 0.148	H-atom parameters constrained
S = 1.03	Δρ_max = 0.42 e Å⁻³
3194 reflections	Δρ_min = −0.49 e Å⁻³
192 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	0.22072 (7)	0.75221 (8)	0.07999 (3)	0.01957 (19)
O1	0.6098 (2)	0.7989 (3)	0.00433 (10)	0.0340 (5)
O2	0.1125 (2)	0.7474 (2)	0.02135 (9)	0.0302 (5)
O3	0.1953 (2)	0.8653 (2)	0.13092 (9)	0.0256 (4)
C1	0.4056 (3)	0.7908 (3)	0.06010 (12)	0.0206 (6)
C2	0.5331 (3)	0.8631 (3)	0.10261 (13)	0.0219 (6)
C3	0.5561 (3)	0.9250 (3)	0.16565 (13)	0.0253 (6)
H3	0.4738	0.9264	0.1918	0.030*
C4	0.7023 (3)	0.9852 (4)	0.18992 (15)	0.0318 (7)
C5	0.8208 (3)	0.9848 (4)	0.15001 (17)	0.0362 (8)
H5	0.9195	1.0266	0.1671	0.043*
C6	0.8006 (3)	0.9267 (4)	0.08721 (16)	0.0361 (8)
H6	0.8817	0.9286	0.0605	0.043*
C7	0.6548 (3)	0.8648 (4)	0.06503 (14)	0.0286 (6)
C8	0.4583 (3)	0.7531 (3)	0.00219 (13)	0.0283 (6)
C9	0.2322 (3)	0.5547 (3)	0.11444 (12)	0.0184 (5)
C10	0.3091 (3)	0.5341 (3)	0.17728 (13)	0.0246 (6)
H10	0.3552	0.6245	0.2010	0.030*
C11	0.3172 (3)	0.3800 (4)	0.20437 (13)	0.0280 (6)
H11	0.3697	0.3637	0.2470	0.034*
C12	0.2487 (3)	0.2487 (3)	0.16934 (14)	0.0294 (6)
H12	0.2542	0.1429	0.1882	0.035*
C13	0.1722 (3)	0.2713 (3)	0.10688 (14)	0.0280 (6)
H13	0.1255	0.1809	0.0833	0.034*
C14	0.1637 (3)	0.4242 (3)	0.07899 (13)	0.0236 (6)
H14	0.1119	0.4400	0.0362	0.028*
C15	0.3901 (4)	0.6744 (4)	−0.05890 (14)	0.0389 (8)
H15A	0.2823	0.6446	−0.0556	0.058*
H15B	0.4494	0.5762	−0.0664	0.058*
H15C	0.3933	0.7503	−0.0953	0.058*
C16	0.7384 (4)	1.0484 (5)	0.25879 (18)	0.0546 (10)
H16A	0.8332	0.9924	0.2791	0.066*
H16B	0.7639	1.1657	0.2561	0.066*
C17	0.6211 (5)	1.0323 (6)	0.30328 (18)	0.0597 (11)
H17A	0.5272	1.0912	0.2855	0.090*
H17B	0.6612	1.0782	0.3459	0.090*
H17C	0.5965	0.9168	0.3083	0.090*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S	0.0181 (3)	0.0187 (3)	0.0212 (3)	0.0015 (2)	−0.0004 (2)	0.0000 (3)
O1	0.0302 (11)	0.0407 (13)	0.0338 (12)	0.0061 (9)	0.0137 (9)	0.0073 (10)
O2	0.0274 (10)	0.0313 (11)	0.0295 (10)	0.0013 (8)	−0.0058 (8)	0.0035 (9)
O3	0.0231 (10)	0.0222 (10)	0.0323 (11)	0.0004 (8)	0.0063 (8)	−0.0056 (8)
C1	0.0222 (13)	0.0177 (13)	0.0225 (13)	0.0017 (10)	0.0049 (10)	0.0029 (11)
C2	0.0177 (13)	0.0195 (13)	0.0289 (14)	0.0024 (10)	0.0045 (11)	0.0070 (11)
C3	0.0202 (14)	0.0259 (15)	0.0299 (15)	−0.0016 (11)	0.0037 (11)	0.0014 (12)
C4	0.0241 (15)	0.0291 (16)	0.0404 (17)	−0.0061 (12)	−0.0025 (12)	0.0039 (13)
C5	0.0175 (14)	0.0372 (18)	0.052 (2)	−0.0044 (12)	−0.0009 (13)	0.0117 (16)
C6	0.0208 (15)	0.0384 (18)	0.051 (2)	0.0047 (12)	0.0116 (14)	0.0179 (16)
C7	0.0264 (15)	0.0277 (15)	0.0329 (15)	0.0067 (12)	0.0082 (12)	0.0084 (13)
C8	0.0306 (15)	0.0293 (15)	0.0256 (14)	0.0069 (12)	0.0058 (12)	0.0089 (13)
C9	0.0171 (12)	0.0192 (13)	0.0191 (13)	−0.0002 (10)	0.0037 (10)	−0.0006 (10)
C10	0.0263 (14)	0.0255 (15)	0.0212 (13)	−0.0015 (11)	−0.0001 (11)	−0.0037 (11)
C11	0.0324 (16)	0.0306 (16)	0.0198 (13)	0.0005 (12)	−0.0008 (11)	0.0012 (12)
C12	0.0373 (16)	0.0208 (14)	0.0317 (15)	0.0006 (12)	0.0104 (13)	0.0044 (13)
C13	0.0333 (15)	0.0224 (15)	0.0289 (15)	−0.0044 (11)	0.0062 (12)	−0.0055 (12)
C14	0.0258 (14)	0.0239 (14)	0.0209 (13)	−0.0016 (11)	0.0023 (11)	−0.0019 (11)
C15	0.052 (2)	0.0423 (19)	0.0232 (15)	0.0102 (16)	0.0090 (14)	−0.0009 (14)
C16	0.0393 (19)	0.066 (3)	0.058 (2)	−0.0246 (18)	0.0013 (17)	−0.017 (2)
C17	0.059 (2)	0.077 (3)	0.042 (2)	−0.018 (2)	−0.0003 (18)	−0.019 (2)

Geometric parameters (Å, º) top

S—O2	1.4386 (19)	C9—C10	1.395 (3)
S—O3	1.4417 (19)	C10—C11	1.381 (4)
S—C1	1.740 (3)	C10—H10	0.950
S—C9	1.767 (3)	C11—C12	1.389 (4)
O1—C8	1.367 (3)	C11—H11	0.950
O1—C7	1.377 (4)	C12—C13	1.388 (4)
C1—C8	1.371 (4)	C12—H12	0.950
C1—C2	1.451 (4)	C13—C14	1.379 (4)
C2—C3	1.390 (4)	C13—H13	0.950
C2—C7	1.391 (4)	C14—H14	0.950
C3—C4	1.397 (4)	C15—H15A	0.980
C3—H3	0.950	C15—H15B	0.980
C4—C5	1.400 (4)	C15—H15C	0.980
C4—C16	1.511 (5)	C16—C17	1.464 (5)
C5—C6	1.374 (5)	C16—H16A	0.990
C5—H5	0.950	C16—H16B	0.990
C6—C7	1.389 (4)	C17—H17A	0.980
C6—H6	0.950	C17—H17B	0.980
C8—C15	1.474 (4)	C17—H17C	0.980
C9—C14	1.388 (4)

O2—S—O3	119.24 (12)	C11—C10—C9	118.9 (2)
O2—S—C1	109.38 (12)	C11—C10—H10	120.6
O3—S—C1	106.76 (12)	C9—C10—H10	120.6
O2—S—C9	108.19 (12)	C10—C11—C12	120.1 (3)
O3—S—C9	107.54 (11)	C10—C11—H11	119.9
C1—S—C9	104.81 (12)	C12—C11—H11	119.9
C8—O1—C7	107.4 (2)	C11—C12—C13	120.3 (3)
C8—C1—C2	107.9 (2)	C11—C12—H12	119.8
C8—C1—S	126.0 (2)	C13—C12—H12	119.8
C2—C1—S	126.13 (19)	C14—C13—C12	120.3 (3)
C3—C2—C7	119.4 (2)	C14—C13—H13	119.9
C3—C2—C1	136.5 (2)	C12—C13—H13	119.9
C7—C2—C1	104.1 (2)	C13—C14—C9	118.9 (2)
C2—C3—C4	118.8 (3)	C13—C14—H14	120.5
C2—C3—H3	120.6	C9—C14—H14	120.5
C4—C3—H3	120.6	C8—C15—H15A	109.5
C3—C4—C5	119.5 (3)	C8—C15—H15B	109.5
C3—C4—C16	122.0 (3)	H15A—C15—H15B	109.5
C5—C4—C16	118.4 (3)	C8—C15—H15C	109.5
C6—C5—C4	122.9 (3)	H15A—C15—H15C	109.5
C6—C5—H5	118.6	H15B—C15—H15C	109.5
C4—C5—H5	118.6	C17—C16—C4	118.9 (3)
C5—C6—C7	116.2 (3)	C17—C16—H16A	107.6
C5—C6—H6	121.9	C4—C16—H16A	107.6
C7—C6—H6	121.9	C17—C16—H16B	107.6
O1—C7—C6	125.9 (3)	C4—C16—H16B	107.6
O1—C7—C2	110.9 (2)	H16A—C16—H16B	107.0
C6—C7—C2	123.2 (3)	C16—C17—H17A	109.5
O1—C8—C1	109.7 (2)	C16—C17—H17B	109.5
O1—C8—C15	115.4 (2)	H17A—C17—H17B	109.5
C1—C8—C15	134.8 (3)	C16—C17—H17C	109.5
C14—C9—C10	121.5 (2)	H17A—C17—H17C	109.5
C14—C9—S	119.7 (2)	H17B—C17—H17C	109.5
C10—C9—S	118.85 (19)

O2—S—C1—C8	−26.7 (3)	C1—C2—C7—C6	179.3 (3)
O3—S—C1—C8	−157.0 (2)	C7—O1—C8—C1	0.8 (3)
C9—S—C1—C8	89.1 (3)	C7—O1—C8—C15	−178.2 (2)
O2—S—C1—C2	155.7 (2)	C2—C1—C8—O1	−1.1 (3)
O3—S—C1—C2	25.4 (3)	S—C1—C8—O1	−179.00 (19)
C9—S—C1—C2	−88.5 (2)	C2—C1—C8—C15	177.7 (3)
C8—C1—C2—C3	−179.7 (3)	S—C1—C8—C15	−0.2 (5)
S—C1—C2—C3	−1.8 (5)	O2—S—C9—C14	10.3 (2)
C8—C1—C2—C7	0.9 (3)	O3—S—C9—C14	140.3 (2)
S—C1—C2—C7	178.8 (2)	C1—S—C9—C14	−106.4 (2)
C7—C2—C3—C4	−1.0 (4)	O2—S—C9—C10	−169.12 (19)
C1—C2—C3—C4	179.6 (3)	O3—S—C9—C10	−39.1 (2)
C2—C3—C4—C5	1.3 (4)	C1—S—C9—C10	74.3 (2)
C2—C3—C4—C16	−177.6 (3)	C14—C9—C10—C11	0.2 (4)
C3—C4—C5—C6	−0.3 (5)	S—C9—C10—C11	179.6 (2)
C16—C4—C5—C6	178.6 (3)	C9—C10—C11—C12	−0.4 (4)
C4—C5—C6—C7	−0.9 (5)	C10—C11—C12—C13	0.2 (4)
C8—O1—C7—C6	−179.9 (3)	C11—C12—C13—C14	0.1 (4)
C8—O1—C7—C2	−0.2 (3)	C12—C13—C14—C9	−0.3 (4)
C5—C6—C7—O1	−179.2 (3)	C10—C9—C14—C13	0.1 (4)
C5—C6—C7—C2	1.2 (4)	S—C9—C14—C13	−179.2 (2)
C3—C2—C7—O1	−179.9 (2)	C3—C4—C16—C17	5.8 (6)
C1—C2—C7—O1	−0.4 (3)	C5—C4—C16—C17	−173.1 (3)
C3—C2—C7—C6	−0.3 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15C···Cg2ⁱ	0.98	2.80	3.592 (4)	139
C16—H16B···Cg2ⁱⁱ	0.98	3.21	3.903 (4)	128

Symmetry codes: (i) −x+1, −y+2, −z; (ii) −x+3/2, y+1/2, −z+1/2.

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)	8.7009 (4), 8.2019 (4), 20.682 (1)
β (°)	97.301 (1)
V (Å³)	1463.98 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.40 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	8693, 3194, 2264
R_int	0.048
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.148, 1.03
No. of reflections	3194
No. of parameters	192
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.42, −0.49

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
C15—H15C···Cg2ⁱ	0.98	2.80	3.592 (4)	139.0
C16—H16B···Cg2ⁱⁱ	0.98	3.21	3.903 (4)	128.0

Symmetry codes: (i) −x+1, −y+2, −z; (ii) −x+3/2, y+1/2, −z+1/2.

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. (2008a). Acta Cryst. E64, o793. Web of Science CSD CrossRef IUCr Journals Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2008b). Acta Cryst. E64, o794. 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 6| June 2008| Page o1016

doi:10.1107/S1600536808012877

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