5-Chloro-3-cyclo­hexyl­sulfonyl-2-methyl-1-benzofuran

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

doi:10.1107/S1600536811008270

organic compounds

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ISSN: 2056-9890

Volume 67| Part 4| April 2011| Page o828

doi:10.1107/S1600536811008270

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5-Chloro-3-cyclohexylsulfonyl-2-methyl-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 17 February 2011; accepted 4 March 2011; online 9 March 2011)

In the title compound, C₁₅H₁₇ClO₃S, the cyclohexyl ring adopts a chair conformation. In the crystal, molecules are linked through weak intermolecular C—H⋯O and C—H⋯π interactions.

Related literature

For the pharmacological activity of benzofuran compounds, see: Aslam et al. (2006 ); Galal et al. (2009 ); Khan et al. (2005 ). For natural products with benzofuran rings, see: Akgul & Anil (2003 ); Soekamto et al. (2003 ). For structural studies of related 3-arylsulfonyl-5-chloro-2-methyl-1-benzofuran derivatives, see: Choi et al. (2008 , 2010 ).

Experimental

Crystal data

C₁₅H₁₇ClO₃S
M_r = 312.80
Monoclinic, P 2₁ /c
a = 14.3135 (2) Å
b = 9.2829 (2) Å
c = 11.3433 (2) Å
β = 107.566 (1)°
V = 1436.91 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.42 mm⁻¹
T = 173 K
0.29 × 0.18 × 0.11 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.891, T_max = 0.954
13251 measured reflections
3287 independent reflections
2856 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.093
S = 1.07
3287 reflections
182 parameters
H-atom parameters constrained
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O3ⁱ	0.95	2.54	3.2630 (19)	133
C10—H10⋯O2ⁱⁱ	1.00	2.42	3.3899 (19)	162
C9—H9C⋯Cgⁱⁱⁱ	0.98	2.69	3.577 (2)	151
Symmetry codes: (i) x, y-1, z; (ii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (iii) -x+1, -y+1, -z+1.

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/S1600536811008270/bh2340sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811008270/bh2340Isup2.hkl

checkCIF report

Comment top

Many compounds containing a benzofuran ring exhibit interesting pharmacological properties such as antifungal, antitumor and antiviral, and antimicrobial activities (Aslam et al., 2006; Galal et al., 2009; Khan et al., 2005). These compounds occur in a wide range of natural products (Akgul & Anil, 2003; Soekamto et al., 2003). As a part of our ongoing study of the substituent effect on the solid state structures of 3-arylsulfonyl-5-chloro-2-methyl-1-benzofuran analogues (Choi et al., 2008, 2010), 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 0.009 (1) Å from the least-squares plane defined by the nine constituent atoms. The cyclohexyl ring is in the chair form. The molecular packing (Fig. 2) is stabilized by weak intermolecular C–H···O hydrogen bonds; the first one between a benzene H atom and the O atom of the sulfonyl unit (Table 1: C6–H6···O3ⁱ), and the second one between a cyclohexyl H atom and the O atom of the sulfonyl unit (Table 1: C10–H10···O2ⁱⁱ). The crystal packing (Fig. 2) is further stabilized by intermolecular C–H···π interactions between a methyl H atoms and the benzene rings (Table 1: C9–H9C···Cgⁱⁱⁱ, Cg is the centroid of the C2···C7 benzene ring).

Related literature top

For the pharmacological activity of benzofuran compounds, see: Aslam et al. (2006); Galal et al. (2009); Khan et al. (2005). For natural products with benzofuran rings, see: Akgul & Anil (2003); Soekamto et al. (2003). For structural studies of related 3-arylsulfonyl-5-chloro-2-methyl-1-benzofuran derivatives, see: Choi et al. (2008, 2010).

Experimental top

77% 3-chloroperoxybenzoic acid (515 mg, 2.3 mmol) was added in small portions to a stirred solution of 5-chloro-3-cyclohexylsulfanyl-2-methyl-1-benzofuran (389 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, 4:1 v/v) to afford the title compound as a colorless solid [yield 73%, m.p. 440-441 K; R_f = 0.63 (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 ethyl acetate 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. Displacement ellipsoids are drawn at the 50% probability level and H atoms are presented as small spheres of arbitrary radius.
	Fig. 2. A view of the C–H···O and C–H···π interactions (dotted lines) in the crystal structure of the title compound [Symmetry codes: (i) x, y-1, z; (ii) x, -y+3/2, z-1/2; (iii) -x+1, -y+1, -z+1; (iv) x, -y+3/2, z+1/2; (v) x, y+1, z].

5-Chloro-3-cyclohexylsulfonyl-2-methyl-1-benzofuran top

Crystal data top

C₁₅H₁₇ClO₃S	F(000) = 656
M_r = 312.80	D_x = 1.446 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 440 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 14.3135 (2) Å	Cell parameters from 5109 reflections
b = 9.2829 (2) Å	θ = 2.7–27.5°
c = 11.3433 (2) Å	µ = 0.42 mm⁻¹
β = 107.566 (1)°	T = 173 K
V = 1436.91 (4) Å³	Block, colourless
Z = 4	0.29 × 0.18 × 0.11 mm

Data collection top

Bruker SMART APEXII CCD diffractometer	3287 independent reflections
Radiation source: rotating anode	2856 reflections with I > 2σ(I)
Graphite multilayer monochromator	R_int = 0.027
Detector resolution: 10.0 pixels mm^-1	θ_max = 27.5°, θ_min = 1.5°
ϕ and ω scans	h = −18→18
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −12→10
T_min = 0.891, T_max = 0.954	l = −14→14
13251 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)] = 0.034	Hydrogen site location: difference Fourier map
wR(F²) = 0.093	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0479P)² + 0.5583P] where P = (F_o² + 2F_c²)/3
3287 reflections	(Δ/σ)_max = 0.001
182 parameters	Δρ_max = 0.49 e Å⁻³
0 restraints	Δρ_min = −0.37 e Å⁻³
0 constraints

Crystal data top

C₁₅H₁₇ClO₃S	V = 1436.91 (4) Å³
M_r = 312.80	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.3135 (2) Å	µ = 0.42 mm⁻¹
b = 9.2829 (2) Å	T = 173 K
c = 11.3433 (2) Å	0.29 × 0.18 × 0.11 mm
β = 107.566 (1)°

Data collection top

Bruker SMART APEXII CCD diffractometer	3287 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2856 reflections with I > 2σ(I)
T_min = 0.891, T_max = 0.954	R_int = 0.027
13251 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.093	H-atom parameters constrained
S = 1.07	Δρ_max = 0.49 e Å⁻³
3287 reflections	Δρ_min = −0.37 e Å⁻³
182 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S	0.31521 (3)	0.72877 (4)	0.40822 (3)	0.02105 (11)
Cl	0.18841 (3)	0.20832 (5)	0.64837 (4)	0.03919 (13)
O2	0.28307 (9)	0.73602 (12)	0.51704 (10)	0.0298 (3)
O1	0.43749 (7)	0.36827 (12)	0.34930 (10)	0.0255 (2)
O3	0.38824 (8)	0.82960 (12)	0.39699 (11)	0.0320 (3)
C1	0.35822 (10)	0.55463 (15)	0.40040 (13)	0.0208 (3)
C2	0.33118 (10)	0.42681 (15)	0.45538 (13)	0.0209 (3)
C3	0.27018 (10)	0.39605 (17)	0.52741 (14)	0.0242 (3)
H3	0.2347	0.4694	0.5537	0.029*
C4	0.26403 (11)	0.25316 (18)	0.55855 (15)	0.0266 (3)
C5	0.31494 (11)	0.14251 (17)	0.52184 (15)	0.0294 (3)
H5	0.3075	0.0459	0.5452	0.035*
C6	0.37639 (11)	0.17320 (17)	0.45146 (15)	0.0284 (3)
H6	0.4125	0.1000	0.4260	0.034*
C7	0.38230 (10)	0.31567 (16)	0.42022 (14)	0.0230 (3)
C8	0.42122 (10)	0.51346 (16)	0.33784 (13)	0.0226 (3)
C9	0.47360 (11)	0.59044 (18)	0.26251 (15)	0.0292 (3)
H9A	0.4262	0.6427	0.1956	0.044*
H9B	0.5091	0.5208	0.2272	0.044*
H9C	0.5201	0.6588	0.3148	0.044*
C10	0.21039 (10)	0.74609 (15)	0.27476 (13)	0.0208 (3)
H10	0.2316	0.7276	0.1998	0.025*
C11	0.13094 (11)	0.63719 (17)	0.27601 (15)	0.0285 (3)
H11A	0.1104	0.6511	0.3511	0.034*
H11B	0.1570	0.5382	0.2778	0.034*
C12	0.04281 (12)	0.6570 (2)	0.16061 (17)	0.0362 (4)
H12A	0.0626	0.6364	0.0859	0.043*
H12B	−0.0094	0.5880	0.1628	0.043*
C13	0.00340 (12)	0.8095 (2)	0.15363 (18)	0.0367 (4)
H13A	−0.0523	0.8209	0.0773	0.044*
H13B	−0.0209	0.8278	0.2253	0.044*
C14	0.08265 (12)	0.91795 (19)	0.15367 (16)	0.0338 (4)
H14A	0.0561	1.0166	0.1522	0.041*
H14B	0.1027	0.9049	0.0781	0.041*
C15	0.17212 (11)	0.90049 (16)	0.26764 (15)	0.0274 (3)
H15A	0.2241	0.9684	0.2627	0.033*
H15B	0.1539	0.9231	0.3431	0.033*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S	0.02279 (18)	0.01684 (18)	0.02228 (19)	0.00067 (12)	0.00493 (14)	−0.00147 (13)
Cl	0.0382 (2)	0.0426 (3)	0.0397 (3)	−0.00341 (17)	0.01619 (19)	0.01558 (19)
O2	0.0390 (6)	0.0287 (6)	0.0215 (5)	0.0062 (5)	0.0088 (5)	−0.0033 (4)
O1	0.0275 (5)	0.0225 (5)	0.0282 (6)	0.0036 (4)	0.0111 (4)	−0.0011 (4)
O3	0.0265 (5)	0.0208 (5)	0.0445 (7)	−0.0038 (4)	0.0044 (5)	0.0007 (5)
C1	0.0219 (6)	0.0188 (7)	0.0213 (7)	0.0000 (5)	0.0057 (5)	0.0003 (5)
C2	0.0213 (6)	0.0183 (7)	0.0206 (7)	0.0006 (5)	0.0027 (5)	0.0004 (5)
C3	0.0239 (7)	0.0243 (7)	0.0241 (7)	0.0019 (6)	0.0068 (6)	0.0015 (6)
C4	0.0235 (7)	0.0300 (8)	0.0246 (7)	−0.0025 (6)	0.0047 (6)	0.0063 (6)
C5	0.0329 (8)	0.0203 (7)	0.0302 (8)	−0.0011 (6)	0.0025 (6)	0.0050 (6)
C6	0.0305 (8)	0.0197 (7)	0.0318 (8)	0.0037 (6)	0.0045 (6)	−0.0012 (6)
C7	0.0226 (7)	0.0221 (7)	0.0227 (7)	0.0011 (5)	0.0045 (5)	−0.0011 (6)
C8	0.0220 (6)	0.0221 (7)	0.0220 (7)	−0.0001 (5)	0.0039 (5)	−0.0005 (6)
C9	0.0282 (7)	0.0339 (9)	0.0274 (8)	−0.0029 (6)	0.0114 (6)	0.0012 (7)
C10	0.0214 (7)	0.0206 (7)	0.0196 (7)	0.0007 (5)	0.0052 (5)	0.0002 (5)
C11	0.0274 (7)	0.0225 (7)	0.0326 (8)	−0.0035 (6)	0.0047 (6)	0.0011 (6)
C12	0.0282 (8)	0.0351 (9)	0.0387 (10)	−0.0083 (7)	0.0000 (7)	−0.0002 (8)
C13	0.0231 (8)	0.0417 (10)	0.0403 (10)	0.0006 (7)	0.0022 (7)	0.0053 (8)
C14	0.0286 (8)	0.0321 (9)	0.0363 (9)	0.0039 (6)	0.0030 (7)	0.0096 (7)
C15	0.0264 (7)	0.0211 (7)	0.0319 (8)	0.0014 (6)	0.0046 (6)	0.0030 (6)

Geometric parameters (Å, º) top

S—O3	1.4372 (11)	C9—H9B	0.9800
S—O2	1.4431 (12)	C9—H9C	0.9800
S—C1	1.7416 (15)	C10—C11	1.525 (2)
S—C10	1.7882 (14)	C10—C15	1.528 (2)
Cl—C4	1.7461 (16)	C10—H10	1.0000
O1—C8	1.3673 (18)	C11—C12	1.530 (2)
O1—C7	1.3760 (18)	C11—H11A	0.9900
C1—C8	1.360 (2)	C11—H11B	0.9900
C1—C2	1.447 (2)	C12—C13	1.517 (3)
C2—C7	1.391 (2)	C12—H12A	0.9900
C2—C3	1.393 (2)	C12—H12B	0.9900
C3—C4	1.382 (2)	C13—C14	1.516 (2)
C3—H3	0.9500	C13—H13A	0.9900
C4—C5	1.394 (2)	C13—H13B	0.9900
C5—C6	1.384 (2)	C14—C15	1.529 (2)
C5—H5	0.9500	C14—H14A	0.9900
C6—C7	1.378 (2)	C14—H14B	0.9900
C6—H6	0.9500	C15—H15A	0.9900
C8—C9	1.480 (2)	C15—H15B	0.9900
C9—H9A	0.9800

O3—S—O2	118.27 (7)	C11—C10—C15	111.46 (12)
O3—S—C1	108.80 (7)	C11—C10—S	111.72 (10)
O2—S—C1	107.20 (7)	C15—C10—S	108.96 (10)
O3—S—C10	108.26 (7)	C11—C10—H10	108.2
O2—S—C10	108.50 (7)	C15—C10—H10	108.2
C1—S—C10	105.04 (7)	S—C10—H10	108.2
C8—O1—C7	107.10 (11)	C10—C11—C12	109.68 (13)
C8—C1—C2	107.48 (13)	C10—C11—H11A	109.7
C8—C1—S	126.00 (11)	C12—C11—H11A	109.7
C2—C1—S	126.49 (11)	C10—C11—H11B	109.7
C7—C2—C3	119.53 (13)	C12—C11—H11B	109.7
C7—C2—C1	104.62 (13)	H11A—C11—H11B	108.2
C3—C2—C1	135.84 (13)	C13—C12—C11	110.76 (14)
C4—C3—C2	116.49 (14)	C13—C12—H12A	109.5
C4—C3—H3	121.8	C11—C12—H12A	109.5
C2—C3—H3	121.8	C13—C12—H12B	109.5
C3—C4—C5	123.47 (15)	C11—C12—H12B	109.5
C3—C4—Cl	118.45 (13)	H12A—C12—H12B	108.1
C5—C4—Cl	118.08 (12)	C14—C13—C12	110.68 (14)
C6—C5—C4	120.08 (15)	C14—C13—H13A	109.5
C6—C5—H5	120.0	C12—C13—H13A	109.5
C4—C5—H5	120.0	C14—C13—H13B	109.5
C7—C6—C5	116.40 (14)	C12—C13—H13B	109.5
C7—C6—H6	121.8	H13A—C13—H13B	108.1
C5—C6—H6	121.8	C13—C14—C15	111.43 (14)
O1—C7—C6	125.55 (14)	C13—C14—H14A	109.3
O1—C7—C2	110.42 (13)	C15—C14—H14A	109.3
C6—C7—C2	124.03 (14)	C13—C14—H14B	109.3
C1—C8—O1	110.38 (13)	C15—C14—H14B	109.3
C1—C8—C9	134.19 (14)	H14A—C14—H14B	108.0
O1—C8—C9	115.43 (13)	C10—C15—C14	109.85 (13)
C8—C9—H9A	109.5	C10—C15—H15A	109.7
C8—C9—H9B	109.5	C14—C15—H15A	109.7
H9A—C9—H9B	109.5	C10—C15—H15B	109.7
C8—C9—H9C	109.5	C14—C15—H15B	109.7
H9A—C9—H9C	109.5	H15A—C15—H15B	108.2
H9B—C9—H9C	109.5

O3—S—C1—C8	−29.39 (15)	C3—C2—C7—C6	0.5 (2)
O2—S—C1—C8	−158.38 (13)	C1—C2—C7—C6	−178.90 (14)
C10—S—C1—C8	86.33 (14)	C2—C1—C8—O1	−0.51 (16)
O3—S—C1—C2	152.86 (12)	S—C1—C8—O1	−178.61 (10)
O2—S—C1—C2	23.87 (14)	C2—C1—C8—C9	179.31 (15)
C10—S—C1—C2	−91.41 (13)	S—C1—C8—C9	1.2 (3)
C8—C1—C2—C7	0.17 (16)	C7—O1—C8—C1	0.64 (16)
S—C1—C2—C7	178.26 (11)	C7—O1—C8—C9	−179.21 (12)
C8—C1—C2—C3	−179.09 (16)	O3—S—C10—C11	177.11 (11)
S—C1—C2—C3	−1.0 (2)	O2—S—C10—C11	−53.37 (12)
C7—C2—C3—C4	−0.6 (2)	C1—S—C10—C11	61.01 (12)
C1—C2—C3—C4	178.57 (15)	O3—S—C10—C15	−59.29 (12)
C2—C3—C4—C5	0.0 (2)	O2—S—C10—C15	70.23 (12)
C2—C3—C4—Cl	−179.83 (11)	C1—S—C10—C15	−175.40 (10)
C3—C4—C5—C6	0.7 (2)	C15—C10—C11—C12	57.47 (17)
Cl—C4—C5—C6	−179.44 (12)	S—C10—C11—C12	179.64 (12)
C4—C5—C6—C7	−0.8 (2)	C10—C11—C12—C13	−57.59 (19)
C8—O1—C7—C6	178.58 (14)	C11—C12—C13—C14	57.6 (2)
C8—O1—C7—C2	−0.52 (16)	C12—C13—C14—C15	−56.9 (2)
C5—C6—C7—O1	−178.78 (14)	C11—C10—C15—C14	−56.53 (17)
C5—C6—C7—C2	0.2 (2)	S—C10—C15—C14	179.73 (11)
C3—C2—C7—O1	179.63 (12)	C13—C14—C15—C10	55.92 (19)
C1—C2—C7—O1	0.21 (16)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O3ⁱ	0.95	2.54	3.2630 (19)	133
C10—H10···O2ⁱⁱ	1.00	2.42	3.3899 (19)	162
C9—H9C···Cgⁱⁱⁱ	0.98	2.69	3.577 (2)	151

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₇ClO₃S
M_r	312.80
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	14.3135 (2), 9.2829 (2), 11.3433 (2)
β (°)	107.566 (1)
V (Å³)	1436.91 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.42
Crystal size (mm)	0.29 × 0.18 × 0.11

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.891, 0.954
No. of measured, independent and observed [I > 2σ(I)] reflections	13251, 3287, 2856
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.093, 1.07
No. of reflections	3287
No. of parameters	182
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.49, −0.37

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

Cg is the centroid of the benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O3ⁱ	0.95	2.54	3.2630 (19)	133
C10—H10···O2ⁱⁱ	1.00	2.42	3.3899 (19)	162
C9—H9C···Cgⁱⁱⁱ	0.98	2.69	3.577 (2)	151

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

References

Akgul, Y. Y. & Anil, H. (2003). Phytochemistry, 63, 939–943. Web of Science CrossRef PubMed CAS Google Scholar
Aslam, S. N., Stevenson, P. C., Phythian, S. J., Veitch, N. C. & Hall, D. R. (2006). Tetrahedron, 62, 4214–4226. Web of Science CrossRef CAS Google Scholar
Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2008). Acta Cryst. E64, o1190. Web of Science CSD CrossRef IUCr Journals Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010). Acta Cryst. E66, o2350. Web of Science CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Galal, S. A., Abd El-All, A. S., Abdallah, M. M. & El-Diwani, H. I. (2009). Bioorg. Med. Chem. Lett. 19, 2420–2428. Web of Science CrossRef PubMed CAS Google Scholar
Khan, M. W., Alam, M. J., Rashid, M. A. & Chowdhury, R. (2005). Bioorg. Med. Chem. 13, 4796–4805. 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
Soekamto, N. H., Achmad, S. A., Ghisalberti, E. L., Hakim, E. H. & Syah, Y. M. (2003). Phytochemistry, 64, 831–834. Web of Science CrossRef PubMed CAS Google Scholar

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Volume 67| Part 4| April 2011| Page o828

doi:10.1107/S1600536811008270

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