Isopropyl 2-(4,6-dimethyl-3-methyl­sulfinyl-1-benzofuran-2-yl)acetate

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

doi:10.1107/S1600536808034466

organic compounds

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ISSN: 2056-9890

Volume 64| Part 11| November 2008| Page o2203

doi:10.1107/S1600536808034466

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Isopropyl 2-(4,6-dimethyl-3-methylsulfinyl-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 20 October 2008; accepted 22 October 2008; online 25 October 2008)

Molecules of title compound, C₁₆H₂₀O₄S, which was synthesized by the oxidation of isopropyl 2-(4,6-dimethyl-3-methylsulfanyl-1-benzofuran-2-yl)acetate, interact through C—H⋯π interactions between a methylene H atom and the aromatic carbon ring of the benzofuran ring system, and by C—H⋯O hydrogen bonds. Adjacent stacked molecules exhibit a carbonyl–carbonyl interaction [3.295 (2) Å]. The O atom of the methylsulfinyl group is disordered over two positions with site-occupancy factors of 0.9 and 0.1.

Related literature

For the crystal structures of similar alkyl 2-(3-methylsulfinyl-1-benzofuran- 2-yl)acetate derivatives, see: Choi et al. (2007 , 2008 ). For a review of carbonyl–carbonyl interactions, see: Allen et al. (1998 ).

Experimental

Crystal data

C₁₆H₂₀O₄S
M_r = 308.38
Triclinic, $[P \overline 1]$
a = 6.308 (1) Å
b = 11.340 (2) Å
c = 11.506 (2) Å
α = 81.403 (3)°
β = 77.205 (3)°
γ = 83.167 (4)°
V = 790.4 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 298 (2) K
0.40 × 0.30 × 0.10 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: none
4195 measured reflections
2760 independent reflections
2270 reflections with I > 2σ(I)
R_int = 0.044

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.126
S = 1.05
2760 reflections
202 parameters
7 restraints
H-atom parameters constrained
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9B⋯Cgⁱ	0.97	2.99	3.646 (4)	126
C14—H14A⋯O4Aⁱⁱ	0.96	2.57	3.504 (3)	165
C15—H15C⋯O4Bⁱⁱⁱ	0.96	2.54	3.343 (5)	142
C16—H16A⋯O4A^iv	0.96	2.39	3.333 (3)	168
C16—H16A⋯O4A^iv	0.96	2.39	3.333 (3)	168
Symmetry codes: (i) x-1, y, z; (ii) x+1, y, z; (iii) -x+1, -y+1, -z; (iv) -x, -y+1, -z+1. Cg is the centroid of C2–C7 benzene 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/S1600536808034466/ng2503sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808034466/ng2503Isup2.hkl

checkCIF report

Comment top

This work is related to our previous communications on the synthesis and structure of alkyl 2-(3-methylsulfinyl-1-benzofuran-2-yl)acetate analogues, viz. ethyl 2-(5-methyl-3-methylsulfinyl-1-benzofuran-2-yl)acetate (Choi et al., 2007) and isopropyl 2-(5-methyl-3-methylsulfinyl-1-benzofuran-2-yl) acetate (Choi et al., 2008). Here we report the crystal structure of the title compound, isopropyl 2-(4,6-dimethyl-3-methylsulfinyl-1-benzofuran-2-yl) acetate (Fig. 1).

The benzofuran unit is essentially planar, with a mean deviation of 0.011 (2) Å from the least-squares plane defined by the nine constituent atoms. The O4 atom of the methylsulfinyl group is disordered over two positions with site-occupancy factors fixed at 0.9 (for atom O4A) and 0.1 (for atom O4B) in Fig. 1. The molecular packing (Fig. 2) is stabilized by C—H···π interactions between the hydrogen of 9-methylene group and a benzene ring of benzofuran unit, with a C9—H9B···Cgⁱ separation of 2.99 Å (Fig. 2 & Table 1) (Cg is the centroid of C2–C7 benzene ring, symmetry code as in Fig. 2). The molecular packing is further stabilized by intermolecular C—H···O hydrogen bonds (Table 1). In addition, the crystal packing exhibits a type-II carbonyl–carbonyl interaction (Allen et al., 1998), with C10···O3 ⁱⁱ and O3···C10ⁱⁱ distance of 3.295 (2) Å (symmetry code as in Fig. 2).

Related literature top

For the crystal structures of similar alkyl 2-(3-methylsulfinyl-1-benzofuran- 2-yl)acetate derivatives, see: Choi et al. (2007, 2008). For a review of carbonyl–carbonyl interactions, see: Allen et al. (1998). Cg is the centroid of C2–C7 benzene ring.

Experimental top

77% 3-chloroperoxybenzoic acid (314 mg, 1.40 mmol) was added in small portions to a stirred solution of isopropyl 2-(4,6-dimethyl-3-methylsulfanyl-1-benzofuran-2-yl)acetate (380 mg, 1.30 mmol) in dichloromethane (40 ml) at 273 K. After being stirred for 3 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-ethylcetate, 1:2 v/v) to afford the title compound as a colorless solid [yield 84%, m.p. 357–358 K; R_f = 0.77 (hexane-ethyl acetate, 1;2 v/v)]. Single crystals suitable for X-ray diffraction were prepared by evaporation of a solution of the title compound in acetone at room temperature. Spectroscopic analysis: ¹H NMR (CDCl₃, 400 MHz) δ 1.26 (d, J = 6.24 Hz, 6H), 2.42 (s, 3H), 2.62 (s, 3H), 2.99 (s, 3H), 4.34 (s, 2H), 5.00–5.08 (m, 1H), 6.93 (s, 1H), 7.13 (s, 1H); EI—MS 308 [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 30% probability level.
	Fig. 2. C—H···π and C···O interactions (dotted lines) in the title compound. Cg denotes ring centroid. [Symmetry code: (i) x - 1, y, z; (ii) -x, -y, -z + 1; (iii) x + 1, y, z.]

Isopropyl 2-(4,6-dimethyl-3-methylsulfinyl-1-benzofuran-2-yl)acetate top

Crystal data top

C₁₆H₂₀O₄S	Z = 2
M_r = 308.38	F(000) = 328
Triclinic, P1	D_x = 1.296 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.308 (1) Å	Cell parameters from 2459 reflections
b = 11.340 (2) Å	θ = 2.4–28.0°
c = 11.506 (2) Å	µ = 0.22 mm⁻¹
α = 81.403 (3)°	T = 298 K
β = 77.205 (3)°	Block, colorless
γ = 83.167 (4)°	0.40 × 0.30 × 0.10 mm
V = 790.4 (2) Å³

Data collection top

Bruker SMART CCD diffractometer	2270 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.044
Graphite monochromator	θ_max = 25.0°, θ_min = 2.4°
Detector resolution: 10.0 pixels mm^-1	h = −6→7
ϕ and ω scans	k = −8→13
4195 measured reflections	l = −13→13
2760 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)] = 0.043	Hydrogen site location: difference Fourier map
wR(F²) = 0.126	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0676P)² + 0.1659P] where P = (F_o² + 2F_c²)/3
2760 reflections	(Δ/σ)_max < 0.001
202 parameters	Δρ_max = 0.40 e Å⁻³
7 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₁₆H₂₀O₄S	γ = 83.167 (4)°
M_r = 308.38	V = 790.4 (2) Å³
Triclinic, P1	Z = 2
a = 6.308 (1) Å	Mo Kα radiation
b = 11.340 (2) Å	µ = 0.22 mm⁻¹
c = 11.506 (2) Å	T = 298 K
α = 81.403 (3)°	0.40 × 0.30 × 0.10 mm
β = 77.205 (3)°

Data collection top

Bruker SMART CCD diffractometer	2270 reflections with I > 2σ(I)
4195 measured reflections	R_int = 0.044
2760 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	7 restraints
wR(F²) = 0.126	H-atom parameters constrained
S = 1.06	Δρ_max = 0.40 e Å⁻³
2760 reflections	Δρ_min = −0.27 e Å⁻³
202 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	Occ. (<1)
S	0.14112 (9)	0.43525 (5)	0.31658 (6)	0.0639 (2)
O1	0.2743 (2)	0.14311 (12)	0.15511 (12)	0.0528 (4)
O2	−0.2895 (2)	0.15214 (13)	0.49041 (11)	0.0503 (4)
O3	0.0716 (2)	0.13761 (14)	0.48320 (14)	0.0612 (4)
O4A	−0.0855 (3)	0.41447 (18)	0.37312 (18)	0.0742 (5)	0.90
O4B	0.082 (3)	0.5555 (7)	0.2602 (15)	0.086 (5)	0.10
C1	0.2493 (3)	0.31729 (18)	0.22999 (17)	0.0471 (5)
C2	0.4558 (3)	0.30687 (18)	0.14521 (17)	0.0480 (5)
C3	0.6322 (3)	0.3783 (2)	0.10060 (19)	0.0573 (5)
C4	0.8036 (4)	0.3295 (3)	0.0188 (2)	0.0697 (7)
H4	0.9231	0.3739	−0.0118	0.084*
C5	0.8091 (4)	0.2190 (3)	−0.0207 (2)	0.0705 (7)
C6	0.6334 (3)	0.1514 (2)	0.0214 (2)	0.0634 (6)
H6	0.6307	0.0778	−0.0044	0.076*
C7	0.4621 (3)	0.19809 (19)	0.10351 (17)	0.0504 (5)
C8	0.1482 (3)	0.21824 (18)	0.23284 (17)	0.0478 (5)
C9	−0.0638 (3)	0.1747 (2)	0.30051 (18)	0.0538 (5)
H9A	−0.0826	0.1005	0.2732	0.065*
H9B	−0.1814	0.2330	0.2825	0.065*
C10	−0.0808 (3)	0.15375 (17)	0.43450 (18)	0.0461 (4)
C11	−0.3372 (3)	0.13159 (19)	0.62208 (17)	0.0523 (5)
H11	−0.2126	0.0850	0.6498	0.063*
C12	−0.3741 (5)	0.2506 (2)	0.6681 (2)	0.0836 (8)
H12A	−0.4951	0.2967	0.6402	0.100*
H12B	−0.2455	0.2927	0.6393	0.100*
H12C	−0.4055	0.2389	0.7543	0.100*
C13	−0.5315 (4)	0.0596 (2)	0.6574 (2)	0.0671 (6)
H13A	−0.4967	−0.0144	0.6234	0.080*
H13B	−0.6524	0.1041	0.6280	0.080*
H13C	−0.5699	0.0430	0.7434	0.080*
C14	0.6363 (4)	0.4994 (2)	0.1375 (2)	0.0748 (7)
H14A	0.7017	0.4908	0.2065	0.112*
H14B	0.4898	0.5360	0.1571	0.112*
H14C	0.7199	0.5488	0.0725	0.112*
C15	1.0074 (4)	0.1738 (4)	−0.1096 (3)	0.1018 (11)
H15A	0.9817	0.0989	−0.1311	0.153*
H15B	1.1329	0.1626	−0.0735	0.153*
H15C	1.0327	0.2313	−0.1804	0.153*
C16	0.3028 (4)	0.3962 (2)	0.4279 (2)	0.0661 (6)
H16A	0.2627	0.4515	0.4863	0.099*
H16B	0.4543	0.3996	0.3905	0.099*
H16C	0.2784	0.3166	0.4669	0.099*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S	0.0584 (4)	0.0639 (4)	0.0712 (4)	0.0072 (3)	−0.0154 (3)	−0.0215 (3)
O1	0.0453 (8)	0.0637 (9)	0.0494 (8)	−0.0128 (6)	0.0000 (6)	−0.0156 (6)
O2	0.0364 (7)	0.0699 (9)	0.0424 (7)	−0.0089 (6)	−0.0025 (6)	−0.0057 (6)
O3	0.0408 (8)	0.0785 (10)	0.0620 (9)	−0.0078 (7)	−0.0115 (7)	0.0015 (7)
O4A	0.0467 (10)	0.0921 (14)	0.0844 (13)	0.0064 (9)	−0.0059 (9)	−0.0346 (10)
O4B	0.088 (9)	0.086 (8)	0.088 (9)	−0.014 (7)	−0.012 (7)	−0.027 (7)
C1	0.0400 (10)	0.0573 (12)	0.0441 (10)	−0.0055 (8)	−0.0075 (8)	−0.0074 (8)
C2	0.0408 (10)	0.0620 (12)	0.0406 (10)	−0.0089 (9)	−0.0087 (8)	−0.0012 (9)
C3	0.0474 (11)	0.0727 (14)	0.0510 (12)	−0.0190 (10)	−0.0111 (9)	0.0069 (10)
C4	0.0452 (12)	0.108 (2)	0.0529 (13)	−0.0264 (12)	−0.0032 (10)	0.0042 (13)
C5	0.0440 (12)	0.116 (2)	0.0469 (12)	−0.0070 (12)	0.0000 (10)	−0.0109 (13)
C6	0.0504 (12)	0.0878 (17)	0.0509 (12)	−0.0058 (11)	−0.0005 (10)	−0.0202 (11)
C7	0.0400 (10)	0.0681 (13)	0.0420 (10)	−0.0106 (9)	−0.0043 (8)	−0.0051 (9)
C8	0.0392 (10)	0.0619 (12)	0.0413 (10)	−0.0055 (9)	−0.0033 (8)	−0.0102 (9)
C9	0.0402 (10)	0.0725 (14)	0.0492 (11)	−0.0129 (9)	−0.0039 (9)	−0.0116 (10)
C10	0.0363 (10)	0.0491 (11)	0.0521 (11)	−0.0078 (8)	−0.0054 (8)	−0.0065 (8)
C11	0.0484 (11)	0.0654 (13)	0.0408 (10)	−0.0062 (9)	−0.0055 (8)	−0.0045 (9)
C12	0.118 (2)	0.0786 (18)	0.0577 (15)	−0.0077 (16)	−0.0186 (15)	−0.0185 (13)
C13	0.0555 (13)	0.0899 (17)	0.0500 (12)	−0.0156 (12)	0.0016 (10)	−0.0021 (11)
C14	0.0683 (15)	0.0767 (17)	0.0809 (17)	−0.0326 (13)	−0.0162 (13)	0.0071 (13)
C15	0.0542 (15)	0.168 (3)	0.0741 (18)	−0.0068 (17)	0.0147 (13)	−0.0319 (19)
C16	0.0635 (14)	0.0744 (15)	0.0670 (14)	−0.0040 (11)	−0.0174 (11)	−0.0257 (12)

Geometric parameters (Å, º) top

C10—O3ⁱ	3.295 (2)	C8—C9	1.490 (3)
S—O4B	1.463 (2)	C9—C10	1.506 (3)
S—O4A	1.464 (2)	C9—H9A	0.9700
S—C1	1.769 (2)	C9—H9B	0.9700
S—C16	1.783 (2)	C11—C12	1.497 (3)
O1—C7	1.378 (2)	C11—C13	1.501 (3)
O1—C8	1.382 (2)	C11—H11	0.9800
O2—C10	1.332 (2)	C12—H12A	0.9600
O2—C11	1.466 (2)	C12—H12B	0.9600
O3—C10	1.199 (2)	C12—H12C	0.9600
C1—C8	1.349 (3)	C13—H13A	0.9600
C1—C2	1.448 (3)	C13—H13B	0.9600
C2—C7	1.382 (3)	C13—H13C	0.9600
C2—C3	1.412 (3)	C14—H14A	0.9600
C3—C4	1.387 (3)	C14—H14B	0.9600
C3—C14	1.502 (4)	C14—H14C	0.9600
C4—C5	1.389 (4)	C15—H15A	0.9600
C4—H4	0.9300	C15—H15B	0.9600
C5—C6	1.380 (3)	C15—H15C	0.9600
C5—C15	1.521 (3)	C16—H16A	0.9600
C6—C7	1.379 (3)	C16—H16B	0.9600
C6—H6	0.9300	C16—H16C	0.9600

O4B—S—O4A	93.2 (8)	O2—C10—C9	109.90 (16)
O4B—S—C1	121.5 (7)	O3—C10—O3ⁱ	79.52 (13)
O4A—S—C1	107.56 (10)	O2—C10—O3ⁱ	83.17 (11)
O4B—S—C16	127.3 (7)	C9—C10—O3ⁱ	107.38 (13)
O4A—S—C16	108.31 (12)	O2—C11—C12	108.31 (17)
C1—S—C16	97.44 (10)	O2—C11—C13	105.86 (16)
C7—O1—C8	106.29 (15)	C12—C11—C13	114.3 (2)
C10—O2—C11	117.50 (15)	O2—C11—H11	109.4
C8—C1—C2	107.41 (17)	C12—C11—H11	109.4
C8—C1—S	124.50 (15)	C13—C11—H11	109.4
C2—C1—S	128.08 (16)	C11—C12—H12A	109.5
C7—C2—C3	119.24 (19)	C11—C12—H12B	109.5
C7—C2—C1	104.92 (17)	H12A—C12—H12B	109.5
C3—C2—C1	135.8 (2)	C11—C12—H12C	109.5
C4—C3—C2	115.5 (2)	H12A—C12—H12C	109.5
C4—C3—C14	121.5 (2)	H12B—C12—H12C	109.5
C2—C3—C14	123.0 (2)	C11—C13—H13A	109.5
C3—C4—C5	124.5 (2)	C11—C13—H13B	109.5
C3—C4—H4	117.7	H13A—C13—H13B	109.5
C5—C4—H4	117.7	C11—C13—H13C	109.5
C6—C5—C4	119.4 (2)	H13A—C13—H13C	109.5
C6—C5—C15	120.6 (3)	H13B—C13—H13C	109.5
C4—C5—C15	120.0 (3)	C3—C14—H14A	109.5
C7—C6—C5	116.9 (2)	C3—C14—H14B	109.5
C7—C6—H6	121.6	H14A—C14—H14B	109.5
C5—C6—H6	121.6	C3—C14—H14C	109.5
O1—C7—C6	124.8 (2)	H14A—C14—H14C	109.5
O1—C7—C2	110.74 (16)	H14B—C14—H14C	109.5
C6—C7—C2	124.4 (2)	C5—C15—H15A	109.5
C1—C8—O1	110.62 (16)	C5—C15—H15B	109.5
C1—C8—C9	134.01 (18)	H15A—C15—H15B	109.5
O1—C8—C9	115.37 (17)	C5—C15—H15C	109.5
C8—C9—C10	113.33 (16)	H15A—C15—H15C	109.5
C8—C9—H9A	108.9	H15B—C15—H15C	109.5
C10—C9—H9A	108.9	S—C16—H16A	109.5
C8—C9—H9B	108.9	S—C16—H16B	109.5
C10—C9—H9B	108.9	H16A—C16—H16B	109.5
H9A—C9—H9B	107.7	S—C16—H16C	109.5
O3—C10—O2	125.19 (18)	H16A—C16—H16C	109.5
O3—C10—C9	124.88 (17)	H16B—C16—H16C	109.5

O4B—S—C1—C8	−114.6 (9)	C5—C6—C7—O1	−179.9 (2)
O4A—S—C1—C8	−9.3 (2)	C5—C6—C7—C2	0.2 (3)
C16—S—C1—C8	102.6 (2)	C3—C2—C7—O1	−178.61 (17)
O4B—S—C1—C2	65.6 (9)	C1—C2—C7—O1	0.9 (2)
O4A—S—C1—C2	170.83 (18)	C3—C2—C7—C6	1.4 (3)
C16—S—C1—C2	−77.2 (2)	C1—C2—C7—C6	−179.1 (2)
C8—C1—C2—C7	−0.5 (2)	C2—C1—C8—O1	−0.2 (2)
S—C1—C2—C7	179.39 (15)	S—C1—C8—O1	179.98 (13)
C8—C1—C2—C3	179.0 (2)	C2—C1—C8—C9	179.6 (2)
S—C1—C2—C3	−1.2 (4)	S—C1—C8—C9	−0.2 (3)
C7—C2—C3—C4	−1.7 (3)	C7—O1—C8—C1	0.7 (2)
C1—C2—C3—C4	179.0 (2)	C7—O1—C8—C9	−179.11 (17)
C7—C2—C3—C14	177.9 (2)	C1—C8—C9—C10	−62.5 (3)
C1—C2—C3—C14	−1.5 (4)	O1—C8—C9—C10	117.28 (19)
C2—C3—C4—C5	0.6 (3)	C11—O2—C10—O3	1.4 (3)
C14—C3—C4—C5	−179.0 (2)	C11—O2—C10—C9	179.47 (16)
C3—C4—C5—C6	0.9 (4)	C11—O2—C10—O3ⁱ	73.42 (14)
C3—C4—C5—C15	−179.2 (2)	C8—C9—C10—O3	−21.3 (3)
C4—C5—C6—C7	−1.3 (3)	C8—C9—C10—O2	160.60 (17)
C15—C5—C6—C7	178.8 (2)	C8—C9—C10—O3ⁱ	−110.50 (16)
C8—O1—C7—C6	179.0 (2)	C10—O2—C11—C12	92.1 (2)
C8—O1—C7—C2	−1.0 (2)	C10—O2—C11—C13	−144.89 (18)

Symmetry code: (i) −x, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9B···Cgⁱⁱ	0.97	2.99	3.646 (4)	126
C14—H14A···O4Aⁱⁱⁱ	0.96	2.57	3.504 (3)	165
C15—H15C···O4B^iv	0.96	2.54	3.343 (5)	142
C16—H16A···O4A^v	0.96	2.39	3.333 (3)	168
C16—H16A···O4A^v	0.96	2.39	3.333 (3)	168

Symmetry codes: (ii) x−1, y, z; (iii) x+1, y, z; (iv) −x+1, −y+1, −z; (v) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₆H₂₀O₄S
M_r	308.38
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	6.308 (1), 11.340 (2), 11.506 (2)
α, β, γ (°)	81.403 (3), 77.205 (3), 83.167 (4)
V (Å³)	790.4 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.40 × 0.30 × 0.10

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	4195, 2760, 2270
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.126, 1.06
No. of reflections	2760
No. of parameters	202
No. of restraints	7
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.27

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
C9—H9B···Cgⁱ	0.97	2.99	3.646 (4)	126.3
C14—H14A···O4Aⁱⁱ	0.96	2.57	3.504 (3)	165.1
C15—H15C···O4Bⁱⁱⁱ	0.96	2.54	3.343 (5)	141.8
C16—H16A···O4A^iv	0.96	2.39	3.333 (3)	167.7
C16—H16A···O4A^iv	0.96	2.39	3.333 (3)	167.7

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

References

Allen, F. H., Baalham, C. A., Lommerse, J. P. M. & Raithby, P. R. (1998). Acta Cryst. B54, 320–329. Web of Science CrossRef CAS IUCr Journals Google Scholar
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, o3839. Web of Science CSD CrossRef IUCr Journals Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2008). Acta Cryst. E64, o2079. 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 11| November 2008| Page o2203

doi:10.1107/S1600536808034466

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