Methyl 2-[5-(4-hydroxy­phen­yl)-3-methyl­sulfanyl-1-benzofuran-2-yl]acetate

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

doi:10.1107/S1600536809037763

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 10| October 2009| Page o2529

doi:10.1107/S1600536809037763

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Methyl 2-[5-(4-hydroxyphenyl)-3-methylsulfanyl-1-benzofuran-2-yl]acetate

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 15 September 2009; accepted 18 September 2009; online 26 September 2009)

In the title compound, C₁₈H₁₆O₄S, the 4-hydroxyphenyl ring is rotated out of the benzofuran plane, making a dihedral angle of 34.52 (6)°. The methyl group of the methylsulfanyl substituent is almost perpendicular to the plane of the benzofuran fragment [100.90 (8)°] and is slightly tilted towards it. The crystal structure is stabilized by intermolecular O—H⋯O hydrogen bonds, and by intermolecular C—H⋯π interactions between a methyl H atom of the methylsulfanyl substituent and the 4-hydroxyphenyl ring.

Related literature

For the crystal structures of similar alkyl 2-[5-(4-hydroxyphenyl)-3-methylsulfanyl-1-benzofuran-2-yl]acetate derivatives, see: Choi et al. (2006 , 2009 ). For the pharmacological activity of benzofuran compounds, see: Howlett et al. (1999 ); Twyman & Allsop (1999 ). For natural products involving a benzofuran ring, see: Akgul & Anil (2003 ); von Reuss & König (2004 ).

Experimental

Crystal data

C₁₈H₁₆O₄S
M_r = 328.37
Monoclinic, P 2₁ /c
a = 13.6661 (6) Å
b = 7.6643 (3) Å
c = 15.6344 (7) Å
β = 95.4731 (6)°
V = 1630.10 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 173 K
0.45 × 0.25 × 0.25 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ) T_min = 0.940, T_max = 0.961
13917 measured reflections
3703 independent reflections
2894 reflections with I > 2σ(I)
R_int = 0.046

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.097
S = 1.08
3703 reflections
213 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4⋯O3ⁱ	0.81 (3)	1.97 (3)	2.7826 (18)	177 (2)
C18—H18C⋯Cgⁱⁱ	0.96	2.88	3.762 (2)	153
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) -x+1, -y+1, -z+1. Cg is the centroid of the C12–C17 phenyl 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/S1600536809037763/si2201sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809037763/si2201Isup2.hkl

checkCIF report

Comment top

Benzofuran ring systems have received considerable interest in view of their pharmacological properties (Howlett et al., 1999; Twyman & Allsop, 1999), and these compounds are occurring in natural products (Akgul & Anil, 2003; von Reuss & König, 2004). As a part of our ongoing studies of the effect of side chain substituents on the solid state structures of alkyl 2-[5-(4-hydroxyphenyl)-3-methylsulfanyl-1-benzofuran-2-yl]acetate analogues (Choi et al., 2006, 2009), we report the crystal structure of the title compound (Fig. 1).

The benzofuran unit is essentially planar, with a mean deviation of 0.005 (1) Å from the least-squares plane defined by the nine constituent atoms. The 4-hydroxyphenyl ring is rotated out of the benzofuran plane, making a dihedral angle of 34.52 (6)°. The methyl group of the methylsulfanyl substituent is tilted towards the plane of the benzofuran unit [100.90 (8)°]. The molecular packing (Fig. 2) is stabilized by intermolecular O—H···O hydrogen bonds between the hydroxy H atom and the oxygen of the C═O unit, with a O4—H4···O3ⁱ (Table 1). The crystal packing (Fig. 2) is further stabilized by intermolecular C—H···π interactions between the methyl H atom of the methylsulfanyl substituent and the 4-hydroxyphenyl ring, with a C18—H18C···Cgⁱⁱ (Table 1; Cg is the centroid of the C12–C17 phenyl ring).

Related literature top

For the crystal structures of similar alkyl 2-[5-(4-hydroxyphenyl)-3-methylsulfanyl-1-benzofuran-2-yl]acetate derivatives, see: Choi et al. (2006, 2009). For the pharmacological activity of benzofuran compounds, see: Howlett et al. (1999); Twyman & Allsop (1999). For natural products involving a benzofuran ring, see: Akgul & Anil (2003); von Reuss & König (2004). Cg is the centroid of the C12–C17 phenyl ring.

Experimental top

2-[5-(4-Hydroxyphenyl)-3-methylsulfanyl-1-benzofuran-2-yl]acetic acid (471 mg, 1.5 mmol) was added to a solution of concentrated sulfuric acid (3 drops) in methanol (20 ml), and the mixture was refluxed for 6h, then cooled. The solvent was evaporated and the residue was poured into water. The mixture was extracted with dichloromethane, dried over magnesium sulfate, filtered and concentrated under vacuum. The residue was purified by column chromatography (benzene–acetone, 9 : 1 v/v) to afford the title compound as a colorless solid [yield 88%, m.p. 446–447 K; R_f = 0.49 (benzene–acetone, 9 : 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.

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 with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as a small cycles of arbitrary radius.
	Fig. 2. O–H···O and C—H···π interactions (dotted lines) in the title compound. Cg denotes the ring centroid. [Symmetry codes: (i) - x + 1, y + 1, - z + 3/2; (ii) - x + 1, - y + 1, - z + 1; (iii) - x + 1, y - 1/2, - z + 3/2.]

Methyl 2-[5-(4-hydroxyphenyl)-3-methylsulfanyl-1-benzofuran-2-yl]acetate top

Crystal data top

C₁₈H₁₆O₄S	F(000) = 688
M_r = 328.37	D_x = 1.338 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6226 reflections
a = 13.6661 (6) Å	θ = 2.6–27.3°
b = 7.6643 (3) Å	µ = 0.22 mm⁻¹
c = 15.6344 (7) Å	T = 173 K
β = 95.4731 (6)°	Block, colorless
V = 1630.10 (12) Å³	0.45 × 0.25 × 0.25 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	3703 independent reflections
Radiation source: fine-focus sealed tube	2894 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.046
Detector resolution: 10.0 pixels mm^-1	θ_max = 27.5°, θ_min = 1.5°
ϕ and ω scans	h = −17→17
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	k = −9→9
T_min = 0.940, T_max = 0.961	l = −20→20
13917 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)] = 0.035	Hydrogen site location: difference Fourier map
wR(F²) = 0.097	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ²(F_o²) + (0.038P)² + 0.664P] where P = (F_o² + 2F_c²)/3
3703 reflections	(Δ/σ)_max < 0.001
213 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₁₈H₁₆O₄S	V = 1630.10 (12) Å³
M_r = 328.37	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.6661 (6) Å	µ = 0.22 mm⁻¹
b = 7.6643 (3) Å	T = 173 K
c = 15.6344 (7) Å	0.45 × 0.25 × 0.25 mm
β = 95.4731 (6)°

Data collection top

Bruker SMART CCD diffractometer	3703 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	2894 reflections with I > 2σ(I)
T_min = 0.940, T_max = 0.961	R_int = 0.046
13917 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.097	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	Δρ_max = 0.30 e Å⁻³
3703 reflections	Δρ_min = −0.25 e Å⁻³
213 parameters

Special details top

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	0.69956 (3)	0.01335 (5)	0.51042 (3)	0.02878 (12)
O1	0.80580 (8)	0.44720 (15)	0.62041 (7)	0.0290 (3)
O2	1.05303 (8)	0.08785 (16)	0.60370 (7)	0.0330 (3)
O3	0.94920 (8)	0.15452 (18)	0.70121 (8)	0.0379 (3)
O4	0.09318 (9)	0.48769 (18)	0.64861 (9)	0.0377 (3)
H4	0.0789 (17)	0.535 (3)	0.6922 (17)	0.061 (8)*
C1	0.72205 (11)	0.2164 (2)	0.55937 (9)	0.0244 (3)
C2	0.65254 (11)	0.33024 (19)	0.59592 (9)	0.0227 (3)
C3	0.55110 (11)	0.3275 (2)	0.60033 (9)	0.0229 (3)
H3	0.5133	0.2362	0.5759	0.027*
C4	0.50698 (11)	0.4634 (2)	0.64192 (9)	0.0236 (3)
C5	0.56623 (11)	0.6008 (2)	0.67804 (10)	0.0277 (3)
H5	0.5365	0.6911	0.7057	0.033*
C6	0.66711 (12)	0.6063 (2)	0.67373 (10)	0.0291 (3)
H6	0.7054	0.6977	0.6974	0.035*
C7	0.70754 (11)	0.4684 (2)	0.63246 (10)	0.0254 (3)
C8	0.81116 (11)	0.2933 (2)	0.57520 (10)	0.0268 (3)
C9	0.91070 (11)	0.2406 (2)	0.55381 (10)	0.0289 (3)
H9A	0.9450	0.3428	0.5354	0.035*
H9B	0.9040	0.1591	0.5062	0.035*
C10	0.97139 (11)	0.1573 (2)	0.62834 (10)	0.0266 (3)
C11	1.11920 (14)	0.0120 (3)	0.67179 (13)	0.0460 (5)
H11A	1.0857	−0.0787	0.6997	0.055*
H11B	1.1403	0.1006	0.7129	0.055*
H11C	1.1754	−0.0362	0.6478	0.055*
C12	0.39861 (11)	0.46601 (19)	0.64631 (10)	0.0227 (3)
C13	0.33451 (11)	0.4013 (2)	0.57879 (10)	0.0246 (3)
H13	0.3604	0.3531	0.5312	0.030*
C14	0.23358 (12)	0.4071 (2)	0.58084 (10)	0.0272 (3)
H14	0.1925	0.3618	0.5354	0.033*
C15	0.19364 (11)	0.4809 (2)	0.65104 (10)	0.0267 (3)
C16	0.25574 (12)	0.5440 (2)	0.71976 (10)	0.0289 (3)
H16	0.2296	0.5919	0.7673	0.035*
C17	0.35686 (12)	0.5352 (2)	0.71715 (10)	0.0273 (3)
H17	0.3979	0.5765	0.7637	0.033*
C18	0.62715 (13)	0.0771 (2)	0.41243 (12)	0.0365 (4)
H18A	0.5645	0.1201	0.4260	0.055*
H18B	0.6176	−0.0220	0.3750	0.055*
H18C	0.6610	0.1671	0.3843	0.055*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0320 (2)	0.0222 (2)	0.0323 (2)	0.00435 (16)	0.00399 (16)	−0.00155 (16)
O1	0.0219 (5)	0.0333 (6)	0.0313 (6)	0.0002 (5)	0.0002 (4)	−0.0056 (5)
O2	0.0240 (6)	0.0455 (7)	0.0299 (6)	0.0094 (5)	0.0041 (4)	0.0007 (5)
O3	0.0297 (6)	0.0546 (8)	0.0309 (6)	0.0048 (6)	0.0105 (5)	0.0091 (6)
O4	0.0244 (6)	0.0501 (8)	0.0394 (7)	−0.0021 (5)	0.0082 (5)	−0.0150 (6)
C1	0.0250 (8)	0.0242 (7)	0.0241 (7)	0.0036 (6)	0.0028 (6)	0.0005 (6)
C2	0.0246 (7)	0.0218 (7)	0.0218 (7)	0.0030 (6)	0.0023 (6)	0.0008 (6)
C3	0.0238 (7)	0.0210 (7)	0.0239 (7)	0.0001 (6)	0.0020 (6)	−0.0002 (6)
C4	0.0253 (7)	0.0241 (8)	0.0212 (7)	0.0030 (6)	0.0011 (6)	0.0011 (6)
C5	0.0279 (8)	0.0268 (8)	0.0277 (8)	0.0059 (6)	−0.0004 (6)	−0.0059 (6)
C6	0.0299 (8)	0.0275 (8)	0.0289 (8)	−0.0013 (7)	−0.0031 (6)	−0.0064 (6)
C7	0.0210 (7)	0.0300 (8)	0.0246 (8)	0.0020 (6)	−0.0006 (6)	−0.0003 (6)
C8	0.0259 (8)	0.0305 (8)	0.0240 (7)	0.0033 (6)	0.0019 (6)	−0.0001 (6)
C9	0.0227 (8)	0.0370 (9)	0.0274 (8)	0.0022 (7)	0.0039 (6)	0.0001 (7)
C10	0.0204 (7)	0.0295 (8)	0.0304 (8)	−0.0025 (6)	0.0055 (6)	−0.0002 (6)
C11	0.0311 (9)	0.0670 (14)	0.0392 (10)	0.0158 (9)	0.0007 (8)	0.0111 (10)
C12	0.0255 (7)	0.0190 (7)	0.0238 (7)	0.0035 (6)	0.0033 (6)	0.0010 (6)
C13	0.0290 (8)	0.0223 (7)	0.0232 (7)	0.0026 (6)	0.0061 (6)	−0.0021 (6)
C14	0.0279 (8)	0.0276 (8)	0.0257 (8)	−0.0010 (6)	0.0006 (6)	−0.0038 (6)
C15	0.0240 (7)	0.0268 (8)	0.0299 (8)	0.0001 (6)	0.0057 (6)	−0.0007 (6)
C16	0.0311 (8)	0.0314 (8)	0.0252 (8)	0.0018 (7)	0.0080 (6)	−0.0054 (7)
C17	0.0295 (8)	0.0284 (8)	0.0239 (8)	0.0017 (6)	0.0015 (6)	−0.0039 (6)
C18	0.0385 (10)	0.0337 (9)	0.0361 (9)	0.0017 (8)	−0.0020 (7)	−0.0023 (7)

Geometric parameters (Å, º) top

S1—C1	1.7488 (16)	C8—C9	1.487 (2)
S1—C18	1.8099 (18)	C9—C10	1.506 (2)
O1—C8	1.3810 (19)	C9—H9A	0.9700
O1—C7	1.3833 (18)	C9—H9B	0.9700
O2—C10	1.3260 (18)	C11—H11A	0.9600
O2—C11	1.451 (2)	C11—H11B	0.9600
O3—C10	1.2067 (19)	C11—H11C	0.9600
O4—C15	1.3708 (19)	C12—C13	1.397 (2)
O4—H4	0.81 (3)	C12—C17	1.398 (2)
C1—C8	1.354 (2)	C13—C14	1.383 (2)
C1—C2	1.447 (2)	C13—H13	0.9300
C2—C7	1.390 (2)	C14—C15	1.392 (2)
C2—C3	1.395 (2)	C14—H14	0.9300
C3—C4	1.395 (2)	C15—C16	1.391 (2)
C3—H3	0.9300	C16—C17	1.388 (2)
C4—C5	1.413 (2)	C16—H16	0.9300
C4—C12	1.489 (2)	C17—H17	0.9300
C5—C6	1.387 (2)	C18—H18A	0.9600
C5—H5	0.9300	C18—H18B	0.9600
C6—C7	1.380 (2)	C18—H18C	0.9600
C6—H6	0.9300

C1—S1—C18	100.90 (8)	O3—C10—O2	124.16 (15)
C8—O1—C7	105.64 (12)	O3—C10—C9	124.63 (14)
C10—O2—C11	115.50 (13)	O2—C10—C9	111.21 (13)
C15—O4—H4	108.3 (17)	O2—C11—H11A	109.5
C8—C1—C2	106.18 (14)	O2—C11—H11B	109.5
C8—C1—S1	125.76 (12)	H11A—C11—H11B	109.5
C2—C1—S1	127.94 (12)	O2—C11—H11C	109.5
C7—C2—C3	119.49 (14)	H11A—C11—H11C	109.5
C7—C2—C1	105.79 (13)	H11B—C11—H11C	109.5
C3—C2—C1	134.71 (14)	C13—C12—C17	117.36 (14)
C2—C3—C4	119.18 (14)	C13—C12—C4	121.01 (13)
C2—C3—H3	120.4	C17—C12—C4	121.63 (14)
C4—C3—H3	120.4	C14—C13—C12	121.72 (14)
C3—C4—C5	119.09 (14)	C14—C13—H13	119.1
C3—C4—C12	120.49 (14)	C12—C13—H13	119.1
C5—C4—C12	120.41 (13)	C13—C14—C15	119.89 (14)
C6—C5—C4	122.50 (14)	C13—C14—H14	120.1
C6—C5—H5	118.8	C15—C14—H14	120.1
C4—C5—H5	118.8	O4—C15—C16	122.95 (14)
C7—C6—C5	116.33 (15)	O4—C15—C14	117.44 (14)
C7—C6—H6	121.8	C16—C15—C14	119.61 (14)
C5—C6—H6	121.8	C17—C16—C15	119.76 (14)
C6—C7—O1	126.20 (14)	C17—C16—H16	120.1
C6—C7—C2	123.41 (14)	C15—C16—H16	120.1
O1—C7—C2	110.39 (13)	C16—C17—C12	121.63 (15)
C1—C8—O1	111.98 (13)	C16—C17—H17	119.2
C1—C8—C9	131.83 (15)	C12—C17—H17	119.2
O1—C8—C9	116.18 (14)	S1—C18—H18A	109.5
C8—C9—C10	112.89 (13)	S1—C18—H18B	109.5
C8—C9—H9A	109.0	H18A—C18—H18B	109.5
C10—C9—H9A	109.0	S1—C18—H18C	109.5
C8—C9—H9B	109.0	H18A—C18—H18C	109.5
C10—C9—H9B	109.0	H18B—C18—H18C	109.5
H9A—C9—H9B	107.8

C18—S1—C1—C8	−114.97 (15)	S1—C1—C8—C9	3.7 (3)
C18—S1—C1—C2	69.48 (15)	C7—O1—C8—C1	−0.77 (17)
C8—C1—C2—C7	−0.71 (17)	C7—O1—C8—C9	179.94 (13)
S1—C1—C2—C7	175.53 (12)	C1—C8—C9—C10	−99.8 (2)
C8—C1—C2—C3	178.91 (17)	O1—C8—C9—C10	79.33 (18)
S1—C1—C2—C3	−4.8 (3)	C11—O2—C10—O3	−2.6 (2)
C7—C2—C3—C4	−0.4 (2)	C11—O2—C10—C9	176.96 (15)
C1—C2—C3—C4	−179.96 (16)	C8—C9—C10—O3	−10.1 (2)
C2—C3—C4—C5	0.4 (2)	C8—C9—C10—O2	170.26 (14)
C2—C3—C4—C12	178.85 (13)	C3—C4—C12—C13	−34.2 (2)
C3—C4—C5—C6	0.1 (2)	C5—C4—C12—C13	144.26 (15)
C12—C4—C5—C6	−178.41 (14)	C3—C4—C12—C17	146.78 (15)
C4—C5—C6—C7	−0.5 (2)	C5—C4—C12—C17	−34.8 (2)
C5—C6—C7—O1	179.75 (14)	C17—C12—C13—C14	0.8 (2)
C5—C6—C7—C2	0.5 (2)	C4—C12—C13—C14	−178.21 (14)
C8—O1—C7—C6	−179.09 (15)	C12—C13—C14—C15	0.8 (2)
C8—O1—C7—C2	0.28 (17)	C13—C14—C15—O4	178.18 (15)
C3—C2—C7—C6	0.0 (2)	C13—C14—C15—C16	−1.8 (2)
C1—C2—C7—C6	179.65 (15)	O4—C15—C16—C17	−178.96 (16)
C3—C2—C7—O1	−179.43 (13)	C14—C15—C16—C17	1.0 (2)
C1—C2—C7—O1	0.26 (17)	C15—C16—C17—C12	0.8 (3)
C2—C1—C8—O1	0.92 (18)	C13—C12—C17—C16	−1.7 (2)
S1—C1—C8—O1	−175.42 (11)	C4—C12—C17—C16	177.40 (15)
C2—C1—C8—C9	−179.93 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O3ⁱ	0.81 (3)	1.97 (3)	2.7826 (18)	177 (2)
C18—H18C···Cgⁱⁱ	0.96	2.88	3.762 (2)	153

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

Experimental details

Crystal data
Chemical formula	C₁₈H₁₆O₄S
M_r	328.37
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	13.6661 (6), 7.6643 (3), 15.6344 (7)
β (°)	95.4731 (6)
V (Å³)	1630.10 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.45 × 0.25 × 0.25

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2000)
T_min, T_max	0.940, 0.961
No. of measured, independent and observed [I > 2σ(I)] reflections	13917, 3703, 2894
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.097, 1.08
No. of reflections	3703
No. of parameters	213
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.25

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
O4—H4···O3ⁱ	0.81 (3)	1.97 (3)	2.7826 (18)	177 (2)
C18—H18C···Cgⁱⁱ	0.96	2.88	3.762 (2)	152.6

Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) −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
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Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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Volume 65| Part 10| October 2009| Page o2529

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