Crystal structure of 2,5-dimethyl-3-(3-methyl­phenyl­sulfon­yl)-1-benzo­furan

Choi, H.D.; Lee, U.

doi:10.1107/S1600536814019369

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 70| Part 9| September 2014| Pages o1073-o1074

doi:10.1107/S1600536814019369

Open

access

Crystal structure of 2,5-dimethyl-3-(3-methylphenylsulfonyl)-1-benzofuran

Hong Dae Choi ^a 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

Edited by L. Fabian, University of East Anglia, England (Received 7 August 2014; accepted 27 August 2014; online 30 August 2014)

In the title compound, C₁₇H₁₆O₃S, the dihedral angle between the plane of the benzofuran ring system [r.m.s. deviation = 0.010 (1) Å] and that of the 3-methylphenyl ring is 79.09 (5)°. Intramolecular C—H⋯O hydrogen bonds are observed. In the crystal, molecules are connected into a chain along the c-axis direction by two different pairs of inversion-generated interactions: C—H⋯π hydrogen bonds between the methyl groups and the benzene rings of the 3-methylphenyl fragments and π–π interactions between the benzene and furan rings of neighbouring molecules [centroid–centroid distance = 3.673 (2) Å].

Keywords: crystal structure; benzofuran; 3-methylphenyl; C—H⋯π hydrogen bonds; π–π interactions.

CCDC reference: 1021292

1. Related literature

For the pharmacological properties of compounds containing a benzofuran moiety, see: Aslam et al. (2009 ); Galal et al. (2009 ); Howlett et al. (1999 ); Khan et al. (2005 ); Ono et al. (2002 ). For natural products with a benzofuran ring, see: Akgul & Anil (2003 ); Soekamto et al. (2003 ). For the synthesis of the starting material, 2,5-dimethyl-3-(3-methylphenylsulfanyl)-1-benzofuran, see: Choi et al. (1999 ). For a related structure, see: Choi et al. (2013 ).

2. Experimental

2.1. Crystal data

C₁₇H₁₆O₃S
M_r = 300.36
Monoclinic, P 2₁ /n
a = 9.8769 (2) Å
b = 11.3190 (2) Å
c = 13.1320 (2) Å
β = 101.951 (1)°
V = 1436.29 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 173 K
0.33 × 0.29 × 0.23 mm

2.1.2. Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.927, T_max = 0.947
13810 measured reflections
3589 independent reflections
2861 reflections with I > 2σ(I)
R_int = 0.035

2.1.3. Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.128
S = 1.08
3589 reflections
193 parameters
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C11–C16 3-methylphenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10C⋯O3	0.98	2.34	3.078 (3)	131
C17—H17B⋯Cg1ⁱ	0.98	2.88	3.478 (2)	121
Symmetry code: (i) -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 for Windows (Farrugia, 2012 ) and DIAMOND (Brandenburg, 1998 ); software used to prepare material for publication: SHELXL97.

Supporting information

CCDC reference: 1021292

Crystal structure: contains datablock I. DOI: 10.1107/S1600536814019369/fy2118sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814019369/fy2118Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814019369/fy2118Isup3.cml

checkCIF report

Comment top

Molecules containing a benzofuran ring show interesting pharmacological properties such as antibacterial and antifungal, antitumor and antiviral, antimicrobial activities (Aslam et al. 2009, Galal et al., 2009, Khan et al., 2005), and they are potential inhibitors of β-amyloid aggregation (Howlett et al., 1999, Ono et al., 2002). These benzofuran compounds are widely occurring in nature (Akgul & Anil, 2003; Soekamto et al., 2003). As a part of our ongoing program of 3-arylsulfonyl-2,5-dimethyl-1-benzofuran derivatives containing 4-methylphenylsulfonyl substituent in 3-position (Choi et al., 2013), we report herein on the crystal structure of the title compound.

In the title molecule (Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.010 (1) Å from the least-squares plane defined by the nine constituent atoms. The 3-methylphenyl ring is essentially planar, with a mean deviation of 0.005 (1) Å from the least-squares plane defined by the six constituent atoms. The dihedral angle formed by the benzofuran ring system and the 3-methylphenyl ring is 79.09 (5)°. In the crystal structure (Fig. 2), molecules are linked along the c-axis direction by two different inversion-generated pairs of C–H···π hydrogen bonds (Table 1, Cg1 is the centroid of the C11-C16 3-methylphenyl ring), and π–π interactions between the benzene and furan rings of neighbouring molecules, with a Cg2···Cg3ⁱⁱ distance of 3.673 (2) Å and an interplanar distance of 3.570 (2) Å resulting in a slippage of 0.864 (2) Å (Cg2 and Cg3 are the centroids of the C2-C7 benzene ring and the C1/C2/C7/O1/C8 furan ring, respectively). In addition, intramolecular C–H···O hydrogen bonds (Table 1) are observed .

Related literature top

For the pharmacological properties of compounds containing a benzofuran moiety, see: Aslam et al. (2009); Galal et al. (2009); Howlett et al. (1999); Khan et al. (2005); Ono et al. (2002). For natural products with a benzofuran ring, see: Akgul & Anil (2003); Soekamto et al. (2003). For the synthesis of the starting material, 2,5-dimethyl-3-(3-methylphenylsulfanyl)-1-benzofuran, see: Choi et al. (1999). For a related structure, see: Choi et al. (2013).

Experimental top

The starting material 2,5-dimethyl-3-(3-methylphenylsulfanyl)-1-benzofuran was prepared by literature method (Choi et al. 1999). 3-Chloroperoxybenzoic acid (77%, 515 mg, 2.3 mmol) was added in small portions to a stirred solution of 2,5-dimethyl-3-(3-methylphenylsulfanyl)-1-benzofuran (295 mg, 1.1 mmol) in dichloromethane (30 mL) at 273 K. After being stirred at room temperature for 8h, the mixture was washed with saturated sodium bicarbonate solution (2 X 20 mL) 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% (241 mg); m.p. 378-379 K; R_f = 0.43 (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 (28 mg) in acetone (15 mL) 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 for Windows (Farrugia, 2012) 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 with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as small spheres of arbitrary radius.
	Fig. 2. A view of the C–H···O, C–H···π and π–π interactions (dotted lines) in the crystal structure of the title compound. H atoms non-participating in hydrogen-bonding were omitted for clarity. [Symmetry codes: (i) - x + 1, - y + 1, - z + 1; (ii) - x + 1, - y + 1, - z.]

2,5-Dimethyl-3-(3-methylphenylsulfonyl)-1-benzofuran top

Crystal data top

C₁₇H₁₆O₃S	F(000) = 632
M_r = 300.36	D_x = 1.389 Mg m⁻³
Monoclinic, P2₁/n	Melting point = 378–379 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 9.8769 (2) Å	Cell parameters from 3458 reflections
b = 11.3190 (2) Å	θ = 2.4–25.7°
c = 13.1320 (2) Å	µ = 0.23 mm⁻¹
β = 101.951 (1)°	T = 173 K
V = 1436.29 (4) Å³	Block, colourless
Z = 4	0.33 × 0.29 × 0.23 mm

Data collection top

Bruker SMART APEXII CCD diffractometer	3589 independent reflections
Radiation source: rotating anode	2861 reflections with I > 2σ(I)
Graphite multilayer monochromator	R_int = 0.035
Detector resolution: 10.0 pixels mm^-1	θ_max = 28.4°, θ_min = 2.4°
ϕ and ω scans	h = −13→12
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −14→15
T_min = 0.927, T_max = 0.947	l = −17→17
13810 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)] = 0.045	Hydrogen site location: difference Fourier map
wR(F²) = 0.128	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0639P)² + 0.4013P] where P = (F_o² + 2F_c²)/3
3589 reflections	(Δ/σ)_max < 0.001
193 parameters	Δρ_max = 0.35 e Å⁻³
0 restraints	Δρ_min = −0.39 e Å⁻³

Crystal data top

C₁₇H₁₆O₃S	V = 1436.29 (4) Å³
M_r = 300.36	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.8769 (2) Å	µ = 0.23 mm⁻¹
b = 11.3190 (2) Å	T = 173 K
c = 13.1320 (2) Å	0.33 × 0.29 × 0.23 mm
β = 101.951 (1)°

Data collection top

Bruker SMART APEXII CCD diffractometer	3589 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2861 reflections with I > 2σ(I)
T_min = 0.927, T_max = 0.947	R_int = 0.035
13810 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.128	H-atom parameters constrained
S = 1.08	Δρ_max = 0.35 e Å⁻³
3589 reflections	Δρ_min = −0.39 e Å⁻³
193 parameters

Special details top

Experimental. ¹H NMR (δ p.p.m., CDCl3, 400 Hz): 7.77-7.83 (m, 2H), 7.67 (s, 1H), 7.34-7.41 (m, 2H), 7.29 (d, J = 8.56 Hz, 1H), 7.10 (dd, J = 8.56 Hz and 1.72 Hz, 1H), 2.78 (s, 3H), 2.45 (s, 3H), 2.40 (s, 3H).

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
S1	0.29608 (4)	0.36272 (4)	0.17488 (3)	0.02967 (14)
O1	0.66012 (13)	0.37182 (11)	0.09943 (10)	0.0345 (3)
O2	0.20801 (13)	0.46348 (11)	0.14867 (10)	0.0366 (3)
O3	0.24998 (14)	0.24951 (11)	0.13176 (10)	0.0384 (3)
C1	0.45457 (18)	0.39515 (16)	0.14324 (12)	0.0287 (4)
C2	0.52013 (17)	0.51022 (15)	0.14998 (12)	0.0273 (4)
C3	0.48710 (18)	0.62452 (15)	0.17608 (13)	0.0297 (4)
H3	0.4006	0.6408	0.1940	0.036*
C4	0.58250 (19)	0.71390 (16)	0.17537 (13)	0.0306 (4)
C5	0.70909 (19)	0.68878 (18)	0.14708 (14)	0.0356 (4)
H5	0.7734	0.7511	0.1468	0.043*
C6	0.74318 (19)	0.57618 (17)	0.11965 (14)	0.0361 (4)
H6	0.8287	0.5597	0.1003	0.043*
C7	0.64635 (19)	0.48979 (16)	0.12196 (13)	0.0306 (4)
C8	0.54295 (19)	0.31645 (16)	0.11373 (13)	0.0315 (4)
C9	0.5504 (2)	0.83842 (17)	0.20414 (15)	0.0385 (4)
H9A	0.4861	0.8749	0.1458	0.058*
H9B	0.6362	0.8845	0.2199	0.058*
H9C	0.5082	0.8367	0.2654	0.058*
C10	0.5398 (2)	0.18729 (17)	0.09586 (16)	0.0410 (5)
H10A	0.6052	0.1485	0.1523	0.062*
H10B	0.5660	0.1704	0.0293	0.062*
H10C	0.4463	0.1574	0.0941	0.062*
C11	0.33565 (18)	0.34750 (15)	0.31193 (14)	0.0293 (4)
C12	0.3862 (2)	0.24005 (16)	0.35446 (15)	0.0350 (4)
H12	0.3997	0.1762	0.3107	0.042*
C13	0.4166 (2)	0.22735 (18)	0.46169 (15)	0.0405 (5)
H13	0.4527	0.1549	0.4922	0.049*
C14	0.3941 (2)	0.32033 (18)	0.52383 (15)	0.0383 (4)
H14	0.4147	0.3104	0.5973	0.046*
C15	0.34268 (18)	0.42744 (16)	0.48270 (14)	0.0321 (4)
C16	0.31430 (18)	0.44131 (16)	0.37446 (14)	0.0306 (4)
H16	0.2806	0.5146	0.3441	0.037*
C17	0.3154 (2)	0.52658 (18)	0.55131 (15)	0.0387 (4)
H17A	0.2158	0.5323	0.5488	0.058*
H17B	0.3486	0.6009	0.5270	0.058*
H17C	0.3641	0.5114	0.6230	0.058*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0298 (2)	0.0263 (2)	0.0322 (2)	−0.00279 (17)	0.00464 (17)	−0.00376 (16)
O1	0.0356 (7)	0.0348 (7)	0.0345 (6)	0.0044 (5)	0.0105 (5)	−0.0018 (5)
O2	0.0326 (7)	0.0328 (7)	0.0437 (7)	0.0038 (5)	0.0062 (6)	0.0015 (6)
O3	0.0415 (8)	0.0308 (7)	0.0403 (7)	−0.0082 (6)	0.0027 (6)	−0.0085 (6)
C1	0.0305 (9)	0.0286 (9)	0.0259 (8)	−0.0005 (7)	0.0036 (7)	−0.0013 (6)
C2	0.0276 (8)	0.0302 (9)	0.0230 (7)	0.0000 (7)	0.0026 (6)	0.0015 (6)
C3	0.0278 (9)	0.0307 (9)	0.0301 (8)	−0.0001 (7)	0.0050 (7)	−0.0002 (7)
C4	0.0318 (9)	0.0306 (9)	0.0272 (8)	−0.0003 (7)	0.0008 (7)	0.0040 (7)
C5	0.0327 (9)	0.0371 (11)	0.0367 (9)	−0.0059 (8)	0.0066 (7)	0.0085 (8)
C6	0.0315 (9)	0.0431 (11)	0.0355 (9)	0.0018 (8)	0.0109 (7)	0.0062 (8)
C7	0.0340 (9)	0.0333 (10)	0.0247 (8)	0.0047 (8)	0.0064 (7)	0.0024 (7)
C8	0.0349 (9)	0.0317 (10)	0.0268 (8)	0.0014 (8)	0.0035 (7)	−0.0018 (7)
C9	0.0408 (11)	0.0325 (10)	0.0415 (10)	−0.0034 (8)	0.0066 (8)	0.0004 (8)
C10	0.0458 (11)	0.0337 (11)	0.0427 (10)	0.0065 (9)	0.0075 (9)	−0.0075 (8)
C11	0.0277 (9)	0.0279 (9)	0.0330 (8)	−0.0063 (7)	0.0078 (7)	−0.0021 (7)
C12	0.0384 (10)	0.0289 (10)	0.0391 (9)	−0.0042 (8)	0.0112 (8)	−0.0014 (8)
C13	0.0472 (12)	0.0335 (11)	0.0416 (10)	−0.0008 (9)	0.0115 (9)	0.0056 (8)
C14	0.0392 (10)	0.0424 (11)	0.0348 (9)	−0.0034 (9)	0.0110 (8)	0.0037 (8)
C15	0.0263 (8)	0.0358 (10)	0.0357 (9)	−0.0053 (7)	0.0098 (7)	−0.0051 (8)
C16	0.0282 (9)	0.0282 (9)	0.0359 (9)	−0.0032 (7)	0.0079 (7)	−0.0016 (7)
C17	0.0403 (11)	0.0411 (11)	0.0363 (9)	−0.0004 (9)	0.0115 (8)	−0.0036 (8)

Geometric parameters (Å, º) top

S1—O2	1.4324 (13)	C9—H9B	0.9800
S1—O3	1.4364 (13)	C9—H9C	0.9800
S1—C1	1.7399 (18)	C10—H10A	0.9800
S1—C11	1.7693 (18)	C10—H10B	0.9800
O1—C8	1.363 (2)	C10—H10C	0.9800
O1—C7	1.380 (2)	C11—C16	1.385 (2)
C1—C8	1.359 (2)	C11—C12	1.387 (3)
C1—C2	1.449 (2)	C12—C13	1.385 (3)
C2—C7	1.390 (2)	C12—H12	0.9500
C2—C3	1.394 (2)	C13—C14	1.378 (3)
C3—C4	1.384 (2)	C13—H13	0.9500
C3—H3	0.9500	C14—C15	1.381 (3)
C4—C5	1.405 (3)	C14—H14	0.9500
C4—C9	1.510 (3)	C15—C16	1.399 (2)
C5—C6	1.385 (3)	C15—C17	1.498 (3)
C5—H5	0.9500	C16—H16	0.9500
C6—C7	1.372 (3)	C17—H17A	0.9800
C6—H6	0.9500	C17—H17B	0.9800
C8—C10	1.480 (3)	C17—H17C	0.9800
C9—H9A	0.9800

O2—S1—O3	119.24 (8)	C4—C9—H9C	109.5
O2—S1—C1	107.84 (8)	H9A—C9—H9C	109.5
O3—S1—C1	108.75 (9)	H9B—C9—H9C	109.5
O2—S1—C11	108.50 (8)	C8—C10—H10A	109.5
O3—S1—C11	107.42 (8)	C8—C10—H10B	109.5
C1—S1—C11	104.08 (8)	H10A—C10—H10B	109.5
C8—O1—C7	106.93 (14)	C8—C10—H10C	109.5
C8—C1—C2	107.54 (16)	H10A—C10—H10C	109.5
C8—C1—S1	126.36 (15)	H10B—C10—H10C	109.5
C2—C1—S1	125.99 (13)	C16—C11—C12	121.31 (17)
C7—C2—C3	119.19 (17)	C16—C11—S1	119.99 (14)
C7—C2—C1	104.37 (15)	C12—C11—S1	118.70 (13)
C3—C2—C1	136.45 (16)	C13—C12—C11	118.97 (17)
C4—C3—C2	118.84 (17)	C13—C12—H12	120.5
C4—C3—H3	120.6	C11—C12—H12	120.5
C2—C3—H3	120.6	C14—C13—C12	119.69 (19)
C3—C4—C5	119.88 (17)	C14—C13—H13	120.2
C3—C4—C9	120.16 (17)	C12—C13—H13	120.2
C5—C4—C9	119.95 (17)	C13—C14—C15	122.04 (18)
C6—C5—C4	122.18 (17)	C13—C14—H14	119.0
C6—C5—H5	118.9	C15—C14—H14	119.0
C4—C5—H5	118.9	C14—C15—C16	118.42 (17)
C7—C6—C5	116.23 (17)	C14—C15—C17	121.33 (17)
C7—C6—H6	121.9	C16—C15—C17	120.24 (17)
C5—C6—H6	121.9	C11—C16—C15	119.54 (17)
C6—C7—O1	125.76 (17)	C11—C16—H16	120.2
C6—C7—C2	123.67 (18)	C15—C16—H16	120.2
O1—C7—C2	110.56 (16)	C15—C17—H17A	109.5
C1—C8—O1	110.60 (16)	C15—C17—H17B	109.5
C1—C8—C10	134.37 (18)	H17A—C17—H17B	109.5
O1—C8—C10	115.02 (16)	C15—C17—H17C	109.5
C4—C9—H9A	109.5	H17A—C17—H17C	109.5
C4—C9—H9B	109.5	H17B—C17—H17C	109.5
H9A—C9—H9B	109.5

O2—S1—C1—C8	−150.31 (15)	C1—C2—C7—O1	−0.07 (18)
O3—S1—C1—C8	−19.69 (18)	C2—C1—C8—O1	−0.81 (19)
C11—S1—C1—C8	94.58 (16)	S1—C1—C8—O1	−177.28 (12)
O2—S1—C1—C2	33.86 (17)	C2—C1—C8—C10	178.18 (19)
O3—S1—C1—C2	164.48 (14)	S1—C1—C8—C10	1.7 (3)
C11—S1—C1—C2	−81.25 (16)	C7—O1—C8—C1	0.77 (18)
C8—C1—C2—C7	0.53 (18)	C7—O1—C8—C10	−178.44 (15)
S1—C1—C2—C7	177.01 (12)	O2—S1—C11—C16	−16.89 (17)
C8—C1—C2—C3	−179.26 (19)	O3—S1—C11—C16	−147.04 (14)
S1—C1—C2—C3	−2.8 (3)	C1—S1—C11—C16	97.75 (15)
C7—C2—C3—C4	−1.3 (2)	O2—S1—C11—C12	162.26 (14)
C1—C2—C3—C4	178.44 (18)	O3—S1—C11—C12	32.11 (17)
C2—C3—C4—C5	1.0 (3)	C1—S1—C11—C12	−83.10 (15)
C2—C3—C4—C9	−179.47 (15)	C16—C11—C12—C13	−0.5 (3)
C3—C4—C5—C6	−0.2 (3)	S1—C11—C12—C13	−179.62 (15)
C9—C4—C5—C6	−179.74 (17)	C11—C12—C13—C14	1.1 (3)
C4—C5—C6—C7	−0.2 (3)	C12—C13—C14—C15	−0.5 (3)
C5—C6—C7—O1	−178.79 (16)	C13—C14—C15—C16	−0.7 (3)
C5—C6—C7—C2	−0.1 (3)	C13—C14—C15—C17	178.39 (19)
C8—O1—C7—C6	178.39 (17)	C12—C11—C16—C15	−0.7 (3)
C8—O1—C7—C2	−0.41 (18)	S1—C11—C16—C15	178.42 (13)
C3—C2—C7—C6	0.9 (3)	C14—C15—C16—C11	1.3 (3)
C1—C2—C7—C6	−178.90 (16)	C17—C15—C16—C11	−177.82 (16)
C3—C2—C7—O1	179.76 (14)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C11–C16 3-methylphenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10C···O3	0.98	2.34	3.078 (3)	131
C17—H17B···Cg1ⁱ	0.98	2.88	3.478 (2)	121

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C11–C16 3-methylphenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10C···O3	0.98	2.34	3.078 (3)	131.2
C17—H17B···Cg1ⁱ	0.98	2.88	3.478 (2)	121.2

Symmetry code: (i) −x+1, −y+1, −z+1.

Acknowledgements

The X-ray centre of the Gyeongsang National University is acknowledged for providing access to the single-crystal diffractometer.

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., Kokubun, T. & Hall, D. R. (2009). Microbiol. Res. 164, 191–195. Web of Science CrossRef PubMed 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. & Lee, U. (2013). Acta Cryst. E69, o817. CSD CrossRef IUCr Journals Google Scholar
Choi, H. D., Seo, P. J. & Son, B. W. (1999). J. Korean Chem. Soc. 43, 606–608. CAS Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS 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
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
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
Ono, M., Kung, M. P., Hou, C. & Kung, H. F. (2002). Nucl. Med. Biol. 29, 633–642. 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

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 70| Part 9| September 2014| Pages o1073-o1074

doi:10.1107/S1600536814019369

Open

access