Monoclinic polymorph of 2,5-dide­oxy-2,5-epithio-1,3:4,6-bis-O-[(R)-phenyl­methyl­ene]-l-iditol

Gibson, J.G.; Cho, J.Y.; Fronczek, F.R.; Watkins, S.F.

doi:10.1107/S1600536812034514

organic compounds

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ISSN: 2056-9890

Volume 68| Part 9| September 2012| Pages o2668-o2669

doi:10.1107/S1600536812034514

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Monoclinic polymorph of 2,5-dideoxy-2,5-epithio-1,3:4,6-bis-O-[(R)-phenylmethylene]-L-iditol †

Jerrell G. Gibson,^a Jung Young Cho,^a Frank R. Fronczek ^a ^* and Steven F. Watkins ^a

^aDepartment of Chemistry, Louisiana State University, Baton Rouge, LA 70803-1804, USA
^*Correspondence e-mail: ffroncz@lsu.edu

(Received 27 July 2012; accepted 2 August 2012; online 11 August 2012)

The title compound C₂₀H₂₀O₄S, is polymorphic. In the tetragonal form, the molecule lies on a crystallographic twofold axis, while the monoclinic form has only approximate C₂ molecular symmetry. The greatest excursion from C₂ symmetry is in the orientation of the two phenyl rings; at 100 K, one of the rings is rotated −37.2 (3)° and the other by 46.9 (3)° from their symmetric (tetragonal) positions. There are only minor differences in the three-ring nucleus; the best molecular fit of the tetragonal and monoclinic forms, both at 100 K and excluding phenyl rings and H atoms, shows an r.m.s. deviation of 0.066 Å. Both forms have the same absolute configuration.

Related literature

For details of the synthesis, see: Rao et al. (1988 ). For the structure of the tetragonal form at 295 K (CCDC refcode WAMRAD), see: Rao et al. (1993 ); and at 100 K (CCDC refcode 851380), see: Gibson et al. (2011 ). For a preliminary report of the structures of both polymorphs at room temperature, see: Fronczek et al. (2002 ). For a description of the Cambridge Structural Database, see: Allen (2002 ). For the determination of the absolute configuration from Bijvoet pairs, see: Hooft et al. (2008 ); Flack (1983 ). For details of the molecular mechanics software used, see: Cambridgesoft (2010 ); Winn & Goodman (2001 ).

Experimental

Crystal data

C₂₀H₂₀O₄S
M_r = 356.42
Monoclinic, P 2₁
a = 6.158 (1) Å
b = 9.223 (2) Å
c = 15.407 (4) Å
β = 95.785 (8)°
V = 870.6 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 100 K
0.25 × 0.22 × 0.10 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997 ) T_min = 0.950, T_max = 0.980
6225 measured reflections
6225 independent reflections
5648 reflections with I > 2σ(I)

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.088
S = 1.05
6225 reflections
227 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.23 e Å⁻³
Absolute structure: Flack (1983), 2730 Bijvoet pairs
Flack parameter: 0.02 (5)

Data collection: COLLECT (Nonius, 2000 ); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SHELXS86 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and IDEAL (Gould et al., 1988 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812034514/mw2079sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812034514/mw2079Isup2.hkl

checkCIF report

Comment top

The tetragonal form of the title compound (I), C₂₀H₂₀O₄S, was determined at 295 K (Rao et al., 1993, hereinafter P4₂₉₅). We re-examined the tetragonal form at 100 K in our laboratory (hereinafter P4₁₀₀) and determined the absolute configuration. These data are deposited at the Cambridge Crystallographic Data Centre (Allen, 2002), CCDC 851380 (Gibson et al., 2011). There is a 2.8% volume decrease upon lowering the temperature from 295 K to 100 K but the molecular symmetry is C₂ at both temperatures and there is no significant change in molecular structure. The best molecular fit (Gould et al., 1988) of all non-H atoms in P4₂₉₅ and P4₁₀₀ yields δ_r.m.s. = 0.022 Å, while excluding the phenyl groups yields δ_r.m.s. = 0.011 Å.

In the monoclinic form at 100 K (P2₁₀₀) the molecular symmetry is C₁. The molecular volume of P2₁₀₀ (435.2 (3) Å³/molecule) is greater than P4₁₀₀ (433.6 (1) Å³/molecule). The thirteen non-H atoms of the three central rings in P2₁₀₀ and P4₁₀₀ are arranged similarly with best molecular fit δ_r.m.s. = 0.066 Å. The most pronounced structural difference between P2₁₀₀ and P4₁₀₀ is in the orientation of the phenyl rings. In P4₁₀₀, two equivalent O—C—C—C torsions of -14.5 (3)° become +32.4 (2)° and -51.7 (2)° in P2₁₀₀. The global minimum conformation of this molecule has been calculated using MM2 (Winn & Goodman, 2001) and confirmed by us (Cambridgesoft, 2010). Like the tetragonal form, the minimum conformation has C₂ symmetry, but the two equivalent O—C—C—C torsions representing the orientation of the phenyl rings are -56°.

Based on the Flack parameter x = 0.02 (5) (Flack, 1983) and Hooft parameters y = 0.00 (3) and P2(true) = 1.000 for 2730 Bijvoet pairs (Hooft et al., 2008), the absolute configurations of the tetragonal and monoclinic forms are identical at 100 K, with stereochemical specification (2R,4aS,5aS,8R,9aS,9bS)-2,8-diphenylhexahydrothieno[3,2 - d:4,5 - d'] bis([1,3]dioxine).

Related literature top

For details of the synthesis, see: Rao et al. (1988). For the structure of the tetragonal form at 295 K (CCDC refcode WAMRAD), see: Rao et al. (1993); and at 100 K (CCDC refcode 851380), see: Gibson et al. (2011). For a preliminary report of the structures of both polymorphs at room temperature, see: Fronczek et al. (2002). For a description of the Cambridge Structural Database, see: Allen (2002). For the determination of the absolute configuration from Bijvoet pairs, see: Hooft et al. (2008); Flack (1983). For details of the ,olecular mechanics software used, see: Cambridgesoft (2010); Winn & Goodman (2001).

Experimental top

The title compound was prepared by Dr. Ronald Voll according to the scheme reported by Rao et al. (1988). A suitable single-crystal was obtained by recrystallization from ethanol.

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS86 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999) and IDEAL (Gould et al., 1988).

Figures top

Fig. 1. View of (I) (50% probability displacement ellipsoids).

2,5-dideoxy-2,5-epithio-1,3:4,6-bis-O-[(R)-phenylmethylene]- L-iditol top

Crystal data top

C₂₀H₂₀O₄S	F(000) = 376
M_r = 356.42	D_x = 1.36 Mg m⁻³
Monoclinic, P2₁	Melting point: 481.5(5) K
Hall symbol: P 2yb	Mo Kα radiation, λ = 0.71073 Å
a = 6.158 (1) Å	Cell parameters from 3254 reflections
b = 9.223 (2) Å	θ = 2.5–33.1°
c = 15.407 (4) Å	µ = 0.21 mm⁻¹
β = 95.785 (8)°	T = 100 K
V = 870.6 (3) Å³	Lath, colorless
Z = 2	0.25 × 0.22 × 0.10 mm

Data collection top

Nonius KappaCCD diffractometer	6225 independent reflections
Radiation source: sealed tube	5648 reflections with I > 2σ(I)
Horizonally mounted graphite crystal monochromator	R_int = 0
Detector resolution: 9 pixels mm^-1	θ_max = 33.1°, θ_min = 2.6°
ω and ϕ scans	h = −9→9
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997)	k = −14→13
T_min = 0.950, T_max = 0.980	l = 0→23
6225 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.037	H-atom parameters constrained
wR(F²) = 0.088	w = 1/[σ²(F_o²) + (0.0366P)² + 0.1562P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
6225 reflections	Δρ_max = 0.29 e Å⁻³
227 parameters	Δρ_min = −0.23 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 2730 Bijvoet pairs
0 constraints	Absolute structure parameter: 0.02 (5)
Primary atom site location: structure-invariant direct methods

Crystal data top

C₂₀H₂₀O₄S	V = 870.6 (3) Å³
M_r = 356.42	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 6.158 (1) Å	µ = 0.21 mm⁻¹
b = 9.223 (2) Å	T = 100 K
c = 15.407 (4) Å	0.25 × 0.22 × 0.10 mm
β = 95.785 (8)°

Data collection top

Nonius KappaCCD diffractometer	6225 independent reflections
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997)	5648 reflections with I > 2σ(I)
T_min = 0.950, T_max = 0.980	R_int = 0
6225 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	H-atom parameters constrained
wR(F²) = 0.088	Δρ_max = 0.29 e Å⁻³
S = 1.05	Δρ_min = −0.23 e Å⁻³
6225 reflections	Absolute structure: Flack (1983), 2730 Bijvoet pairs
227 parameters	Absolute structure parameter: 0.02 (5)
1 restraint

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.

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

	x	y	z	U_iso*/U_eq
C1	0.7808 (2)	0.62050 (15)	0.17832 (8)	0.0169 (2)
H1	0.7275	0.5554	0.1288	0.02*
C2	0.6502 (2)	0.76146 (15)	0.17125 (8)	0.0163 (2)
H2	0.4915	0.7418	0.1554	0.02*
C3	0.7424 (2)	0.85423 (15)	0.10263 (8)	0.0161 (2)
H3	0.681	0.9546	0.1024	0.019*
C4	0.9911 (2)	0.85639 (15)	0.12534 (8)	0.0168 (2)
H4	1.0276	0.9279	0.1734	0.02*
C5	1.1053 (2)	0.90189 (16)	0.04642 (9)	0.0212 (3)
H5A	1.086	1.0075	0.0369	0.025*
H5B	1.2636	0.8822	0.058	0.025*
C6	0.7929 (2)	0.84807 (15)	−0.04585 (8)	0.0167 (2)
H6	0.7622	0.9546	−0.0476	0.02*
C7	0.7107 (2)	0.78161 (14)	−0.13235 (8)	0.0172 (2)
C8	0.4961 (2)	0.73435 (15)	−0.14903 (9)	0.0198 (2)
H8	0.3999	0.7395	−0.1047	0.024*
C9	0.4225 (2)	0.67920 (18)	−0.23124 (8)	0.0229 (2)
H9	0.2771	0.6445	−0.2422	0.027*
C10	0.5608 (2)	0.67481 (19)	−0.29699 (8)	0.0259 (3)
H10	0.509	0.6391	−0.3531	0.031*
C11	0.7744 (3)	0.72253 (17)	−0.28063 (9)	0.0279 (3)
H11	0.8695	0.7192	−0.3255	0.033*
C12	0.8496 (2)	0.77535 (16)	−0.19836 (9)	0.0232 (3)
H12	0.9964	0.8073	−0.1872	0.028*
C13	0.7489 (2)	0.54497 (15)	0.26421 (8)	0.0197 (2)
H13A	0.5992	0.5049	0.2613	0.024*
H13B	0.853	0.4633	0.2733	0.024*
C14	0.6415 (2)	0.76351 (14)	0.32492 (8)	0.0161 (2)
H14	0.4857	0.7313	0.3201	0.019*
C15	0.6900 (2)	0.85965 (15)	0.40299 (8)	0.0168 (2)
C16	0.5382 (2)	0.87628 (16)	0.46339 (9)	0.0204 (3)
H16	0.4012	0.8282	0.4547	0.025*
C17	0.5876 (3)	0.96367 (17)	0.53664 (9)	0.0252 (3)
H17	0.4838	0.9756	0.5777	0.03*
C18	0.7877 (3)	1.03315 (17)	0.54964 (9)	0.0255 (3)
H18	0.8216	1.0916	0.5999	0.031*
C19	0.9390 (2)	1.01740 (18)	0.48917 (9)	0.0263 (3)
H19	1.0756	1.0658	0.4979	0.032*
C20	0.8902 (2)	0.93077 (17)	0.41595 (9)	0.0225 (3)
H20	0.9937	0.92	0.3746	0.027*
O1	1.02017 (15)	0.82585 (11)	−0.03065 (6)	0.01980 (19)
O2	0.68339 (15)	0.78354 (10)	0.02114 (5)	0.01686 (18)
O3	0.68371 (15)	0.84402 (11)	0.24980 (6)	0.01752 (18)
O4	0.78222 (15)	0.64292 (10)	0.33617 (6)	0.01824 (19)
S1	1.06220 (5)	0.67372 (4)	0.16652 (2)	0.01900 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0184 (6)	0.0173 (6)	0.0159 (5)	−0.0023 (4)	0.0049 (4)	−0.0009 (4)
C2	0.0156 (6)	0.0206 (6)	0.0127 (5)	0.0006 (4)	0.0016 (4)	−0.0001 (4)
C3	0.0186 (5)	0.0169 (6)	0.0130 (5)	0.0019 (5)	0.0022 (4)	0.0002 (4)
C4	0.0191 (5)	0.0158 (6)	0.0153 (5)	−0.0015 (5)	0.0009 (4)	0.0016 (4)
C5	0.0204 (6)	0.0236 (7)	0.0196 (6)	−0.0057 (5)	0.0024 (5)	0.0012 (5)
C6	0.0190 (5)	0.0181 (6)	0.0135 (5)	−0.0011 (5)	0.0035 (4)	0.0022 (4)
C7	0.0232 (6)	0.0146 (6)	0.0139 (5)	−0.0006 (5)	0.0029 (4)	0.0016 (4)
C8	0.0241 (6)	0.0181 (6)	0.0176 (5)	−0.0016 (5)	0.0036 (5)	0.0002 (5)
C9	0.0290 (6)	0.0186 (6)	0.0203 (5)	−0.0035 (6)	−0.0009 (5)	−0.0014 (5)
C10	0.0401 (7)	0.0211 (6)	0.0165 (5)	−0.0059 (7)	0.0020 (5)	−0.0034 (6)
C11	0.0402 (8)	0.0282 (8)	0.0168 (6)	−0.0065 (6)	0.0107 (5)	−0.0039 (5)
C12	0.0278 (7)	0.0255 (7)	0.0175 (6)	−0.0051 (5)	0.0073 (5)	−0.0010 (5)
C13	0.0287 (7)	0.0148 (6)	0.0164 (5)	−0.0010 (5)	0.0070 (5)	−0.0002 (4)
C14	0.0169 (5)	0.0195 (6)	0.0123 (5)	0.0018 (4)	0.0037 (4)	−0.0004 (4)
C15	0.0203 (6)	0.0174 (6)	0.0127 (5)	0.0036 (5)	0.0009 (4)	0.0010 (4)
C16	0.0218 (6)	0.0214 (7)	0.0187 (6)	0.0012 (5)	0.0048 (5)	−0.0010 (5)
C17	0.0307 (7)	0.0272 (8)	0.0184 (6)	0.0033 (6)	0.0067 (5)	−0.0028 (5)
C18	0.0309 (7)	0.0258 (7)	0.0190 (6)	0.0045 (6)	−0.0013 (5)	−0.0060 (5)
C19	0.0222 (7)	0.0315 (8)	0.0244 (7)	−0.0006 (6)	−0.0018 (5)	−0.0061 (6)
C20	0.0200 (6)	0.0290 (7)	0.0189 (6)	0.0003 (5)	0.0032 (5)	−0.0045 (5)
O1	0.0184 (4)	0.0243 (5)	0.0173 (4)	−0.0027 (4)	0.0045 (3)	−0.0002 (3)
O2	0.0193 (4)	0.0209 (5)	0.0107 (4)	−0.0027 (3)	0.0031 (3)	0.0004 (3)
O3	0.0244 (5)	0.0167 (4)	0.0119 (4)	0.0027 (4)	0.0038 (3)	0.0003 (3)
O4	0.0243 (4)	0.0164 (5)	0.0139 (4)	0.0029 (3)	0.0017 (3)	−0.0001 (3)
S1	0.01709 (13)	0.01938 (15)	0.02103 (13)	0.00212 (12)	0.00436 (10)	0.00274 (12)

Geometric parameters (Å, º) top

C1—C13	1.5256 (18)	C9—H9	0.95
C1—C2	1.5266 (19)	C10—C11	1.386 (2)
C1—S1	1.8279 (13)	C10—H10	0.95
C1—H1	1	C11—C12	1.3928 (19)
C2—O3	1.4271 (15)	C11—H11	0.95
C2—C3	1.5144 (18)	C12—H12	0.95
C2—H2	1	C13—O4	1.4287 (16)
C3—O2	1.4288 (15)	C13—H13A	0.99
C3—C4	1.5360 (18)	C13—H13B	0.99
C3—H3	1	C14—O4	1.4100 (15)
C4—C5	1.5236 (19)	C14—O3	1.4211 (15)
C4—S1	1.8376 (14)	C14—C15	1.5000 (17)
C4—H4	1	C14—H14	1
C5—O1	1.4322 (16)	C15—C16	1.3925 (18)
C5—H5A	0.99	C15—C20	1.3928 (19)
C5—H5B	0.99	C16—C17	1.3952 (19)
C6—O1	1.4103 (16)	C16—H16	0.95
C6—O2	1.4195 (15)	C17—C18	1.386 (2)
C6—C7	1.5073 (18)	C17—H17	0.95
C6—H6	1	C18—C19	1.390 (2)
C7—C8	1.3907 (19)	C18—H18	0.95
C7—C12	1.3945 (19)	C19—C20	1.390 (2)
C8—C9	1.3974 (18)	C19—H19	0.95
C8—H8	0.95	C20—H20	0.95
C9—C10	1.3879 (19)

C13—C1—C2	109.75 (11)	C11—C10—C9	119.92 (12)
C13—C1—S1	114.52 (9)	C11—C10—H10	120
C2—C1—S1	105.18 (9)	C9—C10—H10	120
C13—C1—H1	109.1	C10—C11—C12	119.93 (13)
C2—C1—H1	109.1	C10—C11—H11	120
S1—C1—H1	109.1	C12—C11—H11	120
O3—C2—C3	104.97 (10)	C11—C12—C7	120.40 (14)
O3—C2—C1	111.34 (10)	C11—C12—H12	119.8
C3—C2—C1	107.41 (11)	C7—C12—H12	119.8
O3—C2—H2	111	O4—C13—C1	111.31 (11)
C3—C2—H2	111	O4—C13—H13A	109.4
C1—C2—H2	111	C1—C13—H13A	109.4
O2—C3—C2	105.99 (10)	O4—C13—H13B	109.4
O2—C3—C4	111.45 (10)	C1—C13—H13B	109.4
C2—C3—C4	106.47 (10)	H13A—C13—H13B	108
O2—C3—H3	110.9	O4—C14—O3	110.58 (10)
C2—C3—H3	110.9	O4—C14—C15	107.30 (10)
C4—C3—H3	110.9	O3—C14—C15	107.83 (11)
C5—C4—C3	110.57 (10)	O4—C14—H14	110.4
C5—C4—S1	114.52 (10)	O3—C14—H14	110.4
C3—C4—S1	105.32 (9)	C15—C14—H14	110.4
C5—C4—H4	108.8	C16—C15—C20	119.77 (12)
C3—C4—H4	108.8	C16—C15—C14	120.53 (12)
S1—C4—H4	108.8	C20—C15—C14	119.69 (12)
O1—C5—C4	111.54 (11)	C15—C16—C17	119.85 (14)
O1—C5—H5A	109.3	C15—C16—H16	120.1
C4—C5—H5A	109.3	C17—C16—H16	120.1
O1—C5—H5B	109.3	C18—C17—C16	120.16 (14)
C4—C5—H5B	109.3	C18—C17—H17	119.9
H5A—C5—H5B	108	C16—C17—H17	119.9
O1—C6—O2	110.77 (10)	C17—C18—C19	120.07 (13)
O1—C6—C7	109.08 (11)	C17—C18—H18	120
O2—C6—C7	109.30 (11)	C19—C18—H18	120
O1—C6—H6	109.2	C18—C19—C20	119.97 (14)
O2—C6—H6	109.2	C18—C19—H19	120
C7—C6—H6	109.2	C20—C19—H19	120
C8—C7—C12	119.57 (12)	C19—C20—C15	120.17 (13)
C8—C7—C6	121.27 (12)	C19—C20—H20	119.9
C12—C7—C6	119.06 (12)	C15—C20—H20	119.9
C7—C8—C9	119.79 (12)	C6—O1—C5	109.91 (10)
C7—C8—H8	120.1	C6—O2—C3	110.49 (10)
C9—C8—H8	120.1	C14—O3—C2	112.91 (10)
C10—C9—C8	120.36 (13)	C14—O4—C13	111.41 (9)
C10—C9—H9	119.8	C1—S1—C4	94.89 (6)
C8—C9—H9	119.8

C13—C1—C2—O3	47.28 (14)	O3—C14—C15—C16	129.50 (12)
S1—C1—C2—O3	−76.39 (11)	O4—C14—C15—C20	67.48 (15)
C13—C1—C2—C3	161.68 (10)	O3—C14—C15—C20	−51.66 (15)
S1—C1—C2—C3	38.02 (11)	C20—C15—C16—C17	−0.2 (2)
O3—C2—C3—O2	−172.01 (9)	C14—C15—C16—C17	178.65 (12)
C1—C2—C3—O2	69.39 (12)	C15—C16—C17—C18	−0.4 (2)
O3—C2—C3—C4	69.21 (12)	C16—C17—C18—C19	0.8 (2)
C1—C2—C3—C4	−49.39 (13)	C17—C18—C19—C20	−0.6 (2)
O2—C3—C4—C5	45.85 (15)	C18—C19—C20—C15	0.0 (2)
C2—C3—C4—C5	160.99 (11)	C16—C15—C20—C19	0.4 (2)
O2—C3—C4—S1	−78.37 (11)	C14—C15—C20—C19	−178.47 (13)
C2—C3—C4—S1	36.77 (11)	O2—C6—O1—C5	−66.02 (13)
C3—C4—C5—O1	−46.70 (16)	C7—C6—O1—C5	173.64 (10)
S1—C4—C5—O1	72.07 (13)	C4—C5—O1—C6	56.52 (14)
O1—C6—C7—C8	153.67 (12)	O1—C6—O2—C3	65.43 (13)
O2—C6—C7—C8	32.42 (17)	C7—C6—O2—C3	−174.35 (10)
O1—C6—C7—C12	−30.07 (16)	C2—C3—O2—C6	−170.15 (10)
O2—C6—C7—C12	−151.31 (12)	C4—C3—O2—C6	−54.71 (13)
C12—C7—C8—C9	0.9 (2)	O4—C14—O3—C2	60.93 (13)
C6—C7—C8—C9	177.15 (13)	C15—C14—O3—C2	177.96 (10)
C7—C8—C9—C10	−1.7 (2)	C3—C2—O3—C14	−169.74 (10)
C8—C9—C10—C11	1.4 (3)	C1—C2—O3—C14	−53.83 (13)
C9—C10—C11—C12	−0.3 (2)	O3—C14—O4—C13	−62.23 (13)
C10—C11—C12—C7	−0.5 (2)	C15—C14—O4—C13	−179.58 (10)
C8—C7—C12—C11	0.2 (2)	C1—C13—O4—C14	57.33 (14)
C6—C7—C12—C11	−176.16 (13)	C13—C1—S1—C4	−134.53 (10)
C2—C1—C13—O4	−49.24 (15)	C2—C1—S1—C4	−13.96 (9)
S1—C1—C13—O4	68.77 (13)	C5—C4—S1—C1	−134.60 (10)
O4—C14—C15—C16	−111.36 (13)	C3—C4—S1—C1	−12.90 (9)

Experimental details

Crystal data
Chemical formula	C₂₀H₂₀O₄S
M_r	356.42
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	100
a, b, c (Å)	6.158 (1), 9.223 (2), 15.407 (4)
β (°)	95.785 (8)
V (Å³)	870.6 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.25 × 0.22 × 0.10

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (SCALEPACK; Otwinowski & Minor, 1997)
T_min, T_max	0.950, 0.980
No. of measured, independent and observed [I > 2σ(I)] reflections	6225, 6225, 5648
R_int	0
(sin θ/λ)_max (Å⁻¹)	0.769

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.088, 1.05
No. of reflections	6225
No. of parameters	227
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.23
Absolute structure	Flack (1983), 2730 Bijvoet pairs
Absolute structure parameter	0.02 (5)

Computer programs: COLLECT (Nonius, 2000), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SHELXS86 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999) and IDEAL (Gould et al., 1988).

Footnotes

†CAS: 151061-72-2.

Acknowledgements

Purchase of the diffractometer was made possible by grant No. LEQSF(1999–2000)-ENH-TR-13, administered by the Louisiana Board of Regents. We thank Dr Ronald Voll for providing the sample.

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