2,4,6-Trimethyl-3-phenyl­sulfinyl-1-benzofuran

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

doi:10.1107/S1600536808021090

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 8| August 2008| Page o1476

doi:10.1107/S1600536808021090

Open

access

2,4,6-Trimethyl-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 1 July 2008; accepted 8 July 2008; online 12 July 2008)

The title compound, C₁₇H₁₆O₂S, was prepared by the oxidation of 2,4,6-trimethyl-3-phenylsulfanyl-1-benzofuran with 3-chloroperoxybenzoic acid. 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 plane of the benzofuran unit [89.88 (8)°] and is tilted slightly towards it. The crystal structure is stabilized by C—H⋯π interactions between a phenyl H atoms and the phenyl and furan rings of neighbouring molecules. In addition, the crystal structure exhibits intermolecular C—H⋯O interactions.

Related literature

For the crystal structures of similar 3-phenylsulfinyl-1-benzofuran derivatives, see: Choi et al. (2007 , 2008 ).

Experimental

Crystal data

C₁₇H₁₆O₂S
M_r = 284.36
Monoclinic, P 2₁ /c
a = 13.493 (2) Å
b = 6.0154 (8) Å
c = 17.269 (2) Å
β = 90.909 (3)°
V = 1401.5 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 173 (2) K
0.40 × 0.40 × 0.30 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: none
7482 measured reflections
2731 independent reflections
2291 reflections with I > 2σ(I)
R_int = 0.067

Refinement

R[F² > 2σ(F²)] = 0.065
wR(F²) = 0.151
S = 1.18
2731 reflections
184 parameters
H-atom parameters constrained
Δρ_max = 0.76 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
C12—H12⋯Cg1ⁱ	0.95	2.88	3.673 (5)	142
C13—H13⋯Cg2ⁱⁱ	0.95	2.95	3.882 (5)	168
C16—H16C⋯O2ⁱⁱⁱ	0.98	2.40	3.366 (4)	167
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) -x+1, -y+1, -z+1; (iii) -x, -y+1, -z+1. Cg1 and Cg2 are the centroids of the C9–C14 phenyl ring and the C1/C2/C7/O1/C8 furan ring, respectively.

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/S1600536808021090/bx2157sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808021090/bx2157Isup2.hkl

checkCIF report

Comment top

This work is related to our communications on the synthesis and structures of 3-phenylsulfinyl-1-benzofuran analogues, viz. 2,5-dimethyl-3-phenylsulfinyl-1-benzofuran (Choi et al., 2007) and 2,4,6,7-tetramethyl-3-phenylsulfinyl-1-benzofuran (Choi et al., 2008). Here we report the crystal structure of the title compound, 2,4,6-trimethyl-3-phenylsulfinyl-1-benzofuran (Fig. 1).

The benzofuran unit is essentially planar, with a mean deviation of 0.013 (2) 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 system [89.88 (8)°] and is tilted slightly towards it. The molecular packing (Fig. 2) is stabilized by two different C—H···π interactions; one between a phenyl H atom and the phenyl ring of the phenylsulfinyl substituent, with a C12—H12···Cg1ⁱ separation of 2.88 Å, and a second between a phenyl H atom and the furan ring of the benzofuran unit, with a C13—H13···Cg2ⁱⁱ separation of 2.95 Å (Fig. 2 and Table 1; Cg1 and Cg2 are the centroids of the C9—C14 phenyl ring and the C1/C2/C7/O1/C8 furan ring, respectively, symmetry code as in Fig. 2). Additionally, 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 3-phenylsulfinyl-1-benzofuran derivatives, see: Choi et al. (2007, 2008). Cg1 and Cg2 are the centroids of the C9–C14 phenyl ring and the C1/C2/C7/O1/C8 furan ring, respectively.

Experimental top

77% 3-Chloroperoxybenzoic acid (247 mg, 1.1 mmol) was added in small portions to a stirred solution of 2,4,6-trimethyl-3-phenylsulfanyl-1-benzofuran (268 mg, 1.0 mmol) in dichloromethane (20 ml) at 273 K. After being stirred at room temperature for 3 h, the mixture was washed with saturated sodium bicarbonate solution and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated under vacuum. The residue was purified by column chromatography (hexane-ethyl acetate, 1:1 v/v) to afford the title compound as a colorless solid [yield 79%, m.p. 404–405 K; R_f = 0.68 (hexane-ethyl acetate, 1:1 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. Spectroscopic analysis: ¹H NMR (CDCl₃, 400 MHz) δ 2.17 (s, 3H), 2.37 (s, 3H), 2.69 (s, 3H), 6.77 (s, 1H), 7.09 (s, 1H), 7.40–7.47 (m, 3H), 7.48–7.52 (m, 2H); EI—MS 284 [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. C—H···π and C—H···O interactions (dotted lines) in the title compound. [Symmetry code: (i) -x + 1, y + 1/2, -z + 3/2; (ii) -x + 1, -y + 1, -z + 1; (iii) -x, -y + 1, -z + 1.]

2,4,6-Trimethyl-3-phenylsulfinyl-1-benzofuran top

Crystal data top

C₁₇H₁₆O₂S	F(000) = 600
M_r = 284.36	D_x = 1.348 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P_2ybc	Cell parameters from 3769 reflections
a = 13.493 (2) Å	θ = 2.4–28.3°
b = 6.0154 (8) Å	µ = 0.23 mm⁻¹
c = 17.269 (2) Å	T = 173 K
β = 90.909 (3)°	Block, colorless
V = 1401.5 (3) Å³	0.40 × 0.40 × 0.30 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	2291 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.067
Graphite monochromator	θ_max = 26.0°, θ_min = 1.5°
Detector resolution: 10.0 pixels mm^-1	h = −16→13
ϕ and ω scans	k = −7→7
7482 measured reflections	l = −21→21
2731 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)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.151	H-atom parameters constrained
S = 1.18	w = 1/[σ²(F_o²) + (0.044P)² + 2.2792P] where P = (F_o² + 2F_c²)/3
2731 reflections	(Δ/σ)_max < 0.001
184 parameters	Δρ_max = 0.76 e Å⁻³
0 restraints	Δρ_min = −0.43 e Å⁻³

Crystal data top

C₁₇H₁₆O₂S	V = 1401.5 (3) Å³
M_r = 284.36	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.493 (2) Å	µ = 0.23 mm⁻¹
b = 6.0154 (8) Å	T = 173 K
c = 17.269 (2) Å	0.40 × 0.40 × 0.30 mm
β = 90.909 (3)°

Data collection top

Bruker SMART CCD diffractometer	2291 reflections with I > 2σ(I)
7482 measured reflections	R_int = 0.067
2731 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.065	0 restraints
wR(F²) = 0.151	H-atom parameters constrained
S = 1.18	Δρ_max = 0.76 e Å⁻³
2731 reflections	Δρ_min = −0.43 e Å⁻³
184 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	0.27007 (6)	0.17129 (13)	0.60901 (4)	0.0260 (2)
O1	0.25645 (15)	0.1919 (3)	0.38328 (11)	0.0233 (5)
O2	0.17960 (18)	0.1863 (4)	0.65645 (13)	0.0381 (6)
C1	0.2432 (2)	0.2412 (5)	0.51168 (16)	0.0207 (6)
C2	0.1875 (2)	0.4202 (5)	0.47392 (15)	0.0187 (6)
C3	0.1297 (2)	0.6036 (5)	0.49618 (16)	0.0195 (6)
C4	0.0910 (2)	0.7354 (5)	0.43702 (16)	0.0205 (6)
H4	0.0517	0.8599	0.4508	0.025*
C5	0.1066 (2)	0.6950 (5)	0.35773 (16)	0.0220 (6)
C6	0.1615 (2)	0.5103 (5)	0.33600 (15)	0.0210 (6)
H6	0.1720	0.4754	0.2831	0.025*
C7	0.1998 (2)	0.3805 (5)	0.39487 (16)	0.0199 (6)
C8	0.2813 (2)	0.1107 (5)	0.45543 (18)	0.0228 (6)
C9	0.3464 (2)	0.4068 (5)	0.63557 (16)	0.0235 (7)
C10	0.3202 (2)	0.5406 (6)	0.69695 (17)	0.0310 (8)
H10	0.2594	0.5171	0.7227	0.037*
C11	0.3838 (3)	0.7098 (6)	0.7205 (2)	0.0384 (9)
H11	0.3653	0.8069	0.7612	0.046*
C12	0.4737 (3)	0.7374 (6)	0.6850 (2)	0.0415 (9)
H12	0.5176	0.8516	0.7019	0.050*
C13	0.5001 (3)	0.5990 (6)	0.6247 (2)	0.0361 (8)
H13	0.5624	0.6179	0.6006	0.043*
C14	0.4362 (2)	0.4331 (6)	0.59928 (18)	0.0278 (7)
H14	0.4539	0.3389	0.5576	0.033*
C15	0.1085 (2)	0.6565 (6)	0.57950 (16)	0.0269 (7)
H15A	0.1651	0.7359	0.6026	0.040*
H15B	0.0974	0.5181	0.6080	0.040*
H15C	0.0492	0.7500	0.5821	0.040*
C16	0.0615 (2)	0.8484 (6)	0.29790 (18)	0.0300 (7)
H16A	0.0769	0.7938	0.2460	0.045*
H16B	0.0889	0.9982	0.3047	0.045*
H16C	−0.0105	0.8530	0.3041	0.045*
C17	0.3438 (3)	−0.0921 (6)	0.4550 (2)	0.0342 (8)
H17A	0.3529	−0.1465	0.5081	0.051*
H17B	0.4084	−0.0567	0.4331	0.051*
H17C	0.3112	−0.2070	0.4235	0.051*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S	0.0282 (4)	0.0237 (4)	0.0258 (4)	−0.0067 (3)	−0.0038 (3)	0.0092 (3)
O1	0.0217 (10)	0.0217 (11)	0.0265 (11)	−0.0011 (9)	0.0024 (8)	−0.0063 (9)
O2	0.0366 (13)	0.0508 (16)	0.0271 (12)	−0.0123 (12)	0.0029 (10)	0.0099 (11)
C1	0.0198 (14)	0.0202 (15)	0.0221 (14)	−0.0066 (12)	−0.0014 (11)	0.0027 (11)
C2	0.0188 (14)	0.0197 (15)	0.0176 (13)	−0.0042 (12)	0.0001 (11)	0.0010 (11)
C3	0.0194 (14)	0.0218 (15)	0.0174 (14)	−0.0064 (12)	0.0015 (11)	−0.0033 (11)
C4	0.0179 (14)	0.0205 (15)	0.0232 (15)	−0.0012 (12)	0.0013 (11)	−0.0014 (11)
C5	0.0194 (14)	0.0253 (16)	0.0212 (14)	−0.0043 (12)	−0.0005 (11)	0.0019 (12)
C6	0.0216 (15)	0.0283 (16)	0.0130 (13)	−0.0039 (13)	−0.0002 (11)	−0.0012 (12)
C7	0.0184 (14)	0.0182 (15)	0.0231 (14)	−0.0036 (11)	0.0001 (11)	−0.0049 (11)
C8	0.0192 (14)	0.0164 (15)	0.0329 (17)	−0.0061 (11)	0.0003 (12)	0.0008 (12)
C9	0.0267 (16)	0.0241 (16)	0.0193 (14)	−0.0033 (13)	−0.0073 (12)	0.0055 (12)
C10	0.0309 (17)	0.041 (2)	0.0210 (15)	0.0025 (15)	−0.0058 (13)	0.0047 (14)
C11	0.050 (2)	0.035 (2)	0.0296 (18)	0.0064 (17)	−0.0146 (16)	−0.0049 (15)
C12	0.047 (2)	0.033 (2)	0.044 (2)	−0.0130 (17)	−0.0219 (17)	0.0051 (16)
C13	0.0270 (17)	0.041 (2)	0.0399 (19)	−0.0118 (15)	−0.0070 (14)	0.0100 (16)
C14	0.0233 (16)	0.0304 (17)	0.0297 (16)	−0.0012 (14)	−0.0025 (13)	0.0007 (14)
C15	0.0338 (17)	0.0292 (17)	0.0179 (14)	−0.0005 (14)	0.0023 (12)	−0.0054 (13)
C16	0.0267 (16)	0.0355 (19)	0.0277 (16)	−0.0005 (14)	−0.0034 (13)	0.0086 (14)
C17	0.0304 (18)	0.0227 (17)	0.050 (2)	0.0015 (14)	0.0054 (15)	0.0032 (15)

Geometric parameters (Å, º) top

S—O2	1.484 (2)	C9—C14	1.382 (4)
S—C1	1.765 (3)	C10—C11	1.388 (5)
S—C9	1.806 (3)	C10—H10	0.9500
O1—C8	1.375 (4)	C11—C12	1.378 (6)
O1—C7	1.385 (4)	C11—H11	0.9500
C1—C8	1.356 (4)	C12—C13	1.384 (5)
C1—C2	1.461 (4)	C12—H12	0.9500
C2—C7	1.398 (4)	C13—C14	1.385 (5)
C2—C3	1.407 (4)	C13—H13	0.9500
C3—C4	1.389 (4)	C14—H14	0.9500
C3—C15	1.506 (4)	C15—H15A	0.9800
C4—C5	1.410 (4)	C15—H15B	0.9800
C4—H4	0.9500	C15—H15C	0.9800
C5—C6	1.390 (4)	C16—H16A	0.9800
C5—C16	1.506 (4)	C16—H16B	0.9800
C6—C7	1.376 (4)	C16—H16C	0.9800
C6—H6	0.9500	C17—H17A	0.9800
C8—C17	1.483 (4)	C17—H17B	0.9800
C9—C10	1.382 (5)	C17—H17C	0.9800

O2—S—C1	110.69 (14)	C9—C10—H10	120.4
O2—S—C9	106.44 (15)	C11—C10—H10	120.4
C1—S—C9	99.35 (13)	C12—C11—C10	120.1 (3)
C8—O1—C7	106.7 (2)	C12—C11—H11	119.9
C8—C1—C2	107.8 (2)	C10—C11—H11	119.9
C8—C1—S	118.0 (2)	C11—C12—C13	120.1 (3)
C2—C1—S	134.2 (2)	C11—C12—H12	119.9
C7—C2—C3	118.4 (3)	C13—C12—H12	119.9
C7—C2—C1	104.0 (2)	C12—C13—C14	120.3 (3)
C3—C2—C1	137.6 (3)	C12—C13—H13	119.8
C4—C3—C2	116.7 (3)	C14—C13—H13	119.8
C4—C3—C15	120.5 (3)	C9—C14—C13	119.0 (3)
C2—C3—C15	122.8 (3)	C9—C14—H14	120.5
C3—C4—C5	123.8 (3)	C13—C14—H14	120.5
C3—C4—H4	118.1	C3—C15—H15A	109.5
C5—C4—H4	118.1	C3—C15—H15B	109.5
C6—C5—C4	119.2 (3)	H15A—C15—H15B	109.5
C6—C5—C16	121.0 (3)	C3—C15—H15C	109.5
C4—C5—C16	119.7 (3)	H15A—C15—H15C	109.5
C7—C6—C5	116.7 (3)	H15B—C15—H15C	109.5
C7—C6—H6	121.6	C5—C16—H16A	109.5
C5—C6—H6	121.6	C5—C16—H16B	109.5
C6—C7—O1	124.0 (3)	H16A—C16—H16B	109.5
C6—C7—C2	125.1 (3)	C5—C16—H16C	109.5
O1—C7—C2	110.8 (2)	H16A—C16—H16C	109.5
C1—C8—O1	110.7 (3)	H16B—C16—H16C	109.5
C1—C8—C17	134.5 (3)	C8—C17—H17A	109.5
O1—C8—C17	114.7 (3)	C8—C17—H17B	109.5
C10—C9—C14	121.2 (3)	H17A—C17—H17B	109.5
C10—C9—S	120.0 (2)	C8—C17—H17C	109.5
C14—C9—S	118.4 (2)	H17A—C17—H17C	109.5
C9—C10—C11	119.2 (3)	H17B—C17—H17C	109.5

O2—S—C1—C8	−135.5 (2)	C3—C2—C7—C6	1.5 (4)
C9—S—C1—C8	112.9 (2)	C1—C2—C7—C6	−178.8 (3)
O2—S—C1—C2	45.8 (3)	C3—C2—C7—O1	−178.6 (2)
C9—S—C1—C2	−65.8 (3)	C1—C2—C7—O1	1.0 (3)
C8—C1—C2—C7	−1.3 (3)	C2—C1—C8—O1	1.1 (3)
S—C1—C2—C7	177.5 (2)	S—C1—C8—O1	−177.90 (18)
C8—C1—C2—C3	178.3 (3)	C2—C1—C8—C17	179.6 (3)
S—C1—C2—C3	−2.9 (5)	S—C1—C8—C17	0.6 (5)
C7—C2—C3—C4	−1.5 (4)	C7—O1—C8—C1	−0.5 (3)
C1—C2—C3—C4	179.0 (3)	C7—O1—C8—C17	−179.3 (2)
C7—C2—C3—C15	177.6 (3)	O2—S—C9—C10	7.6 (3)
C1—C2—C3—C15	−1.9 (5)	C1—S—C9—C10	122.5 (3)
C2—C3—C4—C5	−0.1 (4)	O2—S—C9—C14	−179.8 (2)
C15—C3—C4—C5	−179.3 (3)	C1—S—C9—C14	−64.9 (3)
C3—C4—C5—C6	1.8 (4)	C14—C9—C10—C11	2.5 (5)
C3—C4—C5—C16	−179.9 (3)	S—C9—C10—C11	174.8 (2)
C4—C5—C6—C7	−1.8 (4)	C9—C10—C11—C12	−2.6 (5)
C16—C5—C6—C7	179.9 (3)	C10—C11—C12—C13	1.2 (5)
C5—C6—C7—O1	−179.6 (3)	C11—C12—C13—C14	0.5 (5)
C5—C6—C7—C2	0.2 (4)	C10—C9—C14—C13	−0.8 (5)
C8—O1—C7—C6	179.4 (3)	S—C9—C14—C13	−173.3 (2)
C8—O1—C7—C2	−0.4 (3)	C12—C13—C14—C9	−0.7 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···Cg1ⁱ	0.95	2.88	3.673 (5)	142
C13—H13···Cg2ⁱⁱ	0.95	2.95	3.882 (5)	168
C16—H16C···O2ⁱⁱⁱ	0.98	2.40	3.366 (4)	167

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

Experimental details

Crystal data
Chemical formula	C₁₇H₁₆O₂S
M_r	284.36
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	13.493 (2), 6.0154 (8), 17.269 (2)
β (°)	90.909 (3)
V (Å³)	1401.5 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
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	7482, 2731, 2291
R_int	0.067
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.065, 0.151, 1.18
No. of reflections	2731
No. of parameters	184
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.76, −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
C12—H12···Cg1ⁱ	0.95	2.88	3.673 (5)	141.9
C13—H13···Cg2ⁱⁱ	0.95	2.95	3.882 (5)	167.7
C16—H16C···O2ⁱⁱⁱ	0.98	2.40	3.366 (4)	167.4

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

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, o1143. 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

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 8| August 2008| Page o1476

doi:10.1107/S1600536808021090

Open

access