Dimethyl 2,2'-[butane-1,4-diylbis(sul-fanediyl)]dibenzoate.

The title compound, C(20)H(22)O(4)S(2), was synthesized by the reaction of 1,4-dibromo-butene with methyl thio-salicylate. The aliphatic segment of this ligand is in an all-trans conformation. The bridging chain, -S-(CH(2))(4)-S-, is almost planar (r.m.s. deviation for all non-H atoms: 0.056 Å) and its mean plane forms dihedral angles of 16.60 (7) and 5.80 (2)° with the aromatic rings. In the crystal, the mol-ecules are linked by weak C-H⋯O inter-actions into chains with graph-set notation C(14) along [0 0 1]. The crystal studied was a racemic twin, the ratio of the twin components being 0.27 (9):0.73 (9).

Related literature

For the potential of coordination polymers based on multi­topic bridging ligands and metal centers as functional mat­erials, see: Guo et al. (2002 ▶); Melcer et al. (2001 ▶). For the use of flexible ligands in such structures, see: Bu et al. (2001 ▶); Withersby et al. (1997 ▶). For our studies on the synthesis and structural characterization of divalent sulfur compounds, see: Brito et al. (2004 ▶, 2005 ▶, 2006 ▶). For a related compound, see: Awaleh et al. (2005 ▶). For graph-set notation of hydrogen bonds, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C20H22O4S2

M = 390.5

Orthorhombic,

a = 7.4027 (7) Å

b = 14.2976 (11) Å

c = 17.7396 (13) Å

V = 1877.6 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.31 mm−1

T = 173 K

0.28 × 0.25 × 0.23 mm

Data collection

STOE IPDS II two-circle-diffractometer

Absorption correction: multi-scan (MULABS; Spek, 2003 ▶; Blessing, 1995 ▶) T min = 0.919, T max = 0.933

8050 measured reflections

3437 independent reflections

2244 reflections with I > 2σ(I)

R int = 0.069

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.065

S = 0.73

3437 reflections

239 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.27 e Å−3

Absolute structure: Flack (1983 ▶), 1430 Friedel pairs

Flack parameter: 0.27 (9)

Data collection: X-AREA (Stoe & Cie, 2001 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP (Sheldrick, 2008 ▶) and PLATON (Spek, 2003 ▶; software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809042846/om2290sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809042846/om2290Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C20H22O4S2	F(000) = 824
Mr = 390.5	Dx = 1.381 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4482 reflections
a = 7.4027 (7) Å	θ = 3.4–25.9°
b = 14.2976 (11) Å	µ = 0.31 mm−1
c = 17.7396 (13) Å	T = 173 K
V = 1877.6 (3) Å3	Block, colourless
Z = 4	0.28 × 0.25 × 0.23 mm

STOE IPDS II two-circle-diffractometer	2244 reflections with I > 2σ(I)
graphite	Rint = 0.069
ω scans	θmax = 25.6°, θmin = 3.3°
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995)	h = −8→7
Tmin = 0.919, Tmax = 0.933	k = −17→13
8050 measured reflections	l = −21→20
3437 independent reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.039	w = 1/[σ2(Fo2) + (0.0001P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.065	(Δ/σ)max < 0.001
S = 0.73	Δρmax = 0.16 e Å−3
3437 reflections	Δρmin = −0.27 e Å−3
239 parameters	Extinction correction: SHELXL
0 restraints	Extinction coefficient: 0.0030 (3)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1430 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.27 (9)

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.

	x	y	z	Uiso*/Ueq
S1	0.26565 (13)	0.29690 (6)	0.42902 (3)	0.0257 (2)
S2	0.30831 (13)	0.20540 (6)	0.80343 (4)	0.0292 (2)
O1	0.2673 (5)	0.41362 (15)	0.30785 (10)	0.0449 (8)
O2	0.2727 (4)	0.37231 (15)	0.18638 (9)	0.0340 (6)
O3	0.3720 (4)	0.08601 (17)	0.91935 (11)	0.0359 (7)
O4	0.4816 (4)	0.12269 (18)	1.03289 (10)	0.0369 (7)
C1	0.2650 (6)	0.2191 (2)	0.51027 (13)	0.0249 (8)
H1A	0.1554	0.1794	0.5099	0.03*
H1B	0.3725	0.1779	0.5092	0.03*
C2	0.2678 (6)	0.2809 (2)	0.58124 (13)	0.0264 (8)
H2A	0.3754	0.322	0.5799	0.032*
H2B	0.1591	0.3211	0.5819	0.032*
C3	0.2725 (6)	0.2212 (2)	0.65279 (13)	0.0261 (9)
H3A	0.1607	0.1834	0.6561	0.031*
H3B	0.3766	0.1779	0.6506	0.031*
C4	0.2885 (6)	0.2832 (2)	0.72250 (13)	0.0280 (9)
H4A	0.1803	0.3234	0.7276	0.034*
H4B	0.3964	0.3238	0.7187	0.034*
C11	0.2723 (5)	0.2174 (2)	0.35190 (13)	0.0232 (9)
C12	0.2798 (6)	0.2517 (2)	0.27679 (15)	0.0244 (9)
C13	0.2887 (5)	0.1872 (2)	0.21715 (14)	0.0288 (9)
H13	0.2957	0.2098	0.1669	0.035*
C14	0.2875 (6)	0.0934 (2)	0.22956 (15)	0.0350 (10)
H14	0.2954	0.0511	0.1883	0.042*
C15	0.2747 (6)	0.0593 (2)	0.30303 (15)	0.0339 (9)
H15	0.2696	−0.0061	0.3121	0.041*
C16	0.2695 (6)	0.1219 (2)	0.36288 (14)	0.0282 (9)
H16	0.2638	0.0983	0.4129	0.034*
C17	0.2741 (6)	0.3527 (2)	0.26050 (14)	0.0276 (9)
C18	0.2495 (7)	0.4698 (2)	0.16715 (15)	0.0389 (10)
H18A	0.3472	0.5066	0.1897	0.058*
H18B	0.1331	0.4919	0.1864	0.058*
H18C	0.2525	0.477	0.1122	0.058*
C21	0.3729 (5)	0.2822 (3)	0.87713 (15)	0.0249 (9)
C22	0.4253 (6)	0.2465 (3)	0.94829 (16)	0.0266 (9)
C23	0.4802 (5)	0.3083 (3)	1.00471 (16)	0.0308 (9)
H23	0.5158	0.2841	1.0523	0.037*
C24	0.4840 (6)	0.4036 (3)	0.99282 (17)	0.0349 (10)
H24	0.5217	0.4446	1.0319	0.042*
C25	0.4321 (5)	0.4390 (2)	0.92306 (17)	0.0319 (9)
H25	0.435	0.5045	0.914	0.038*
C26	0.3758 (6)	0.3778 (3)	0.86655 (16)	0.0294 (10)
H26	0.3385	0.4027	0.8194	0.035*
C27	0.4227 (5)	0.1458 (3)	0.96319 (16)	0.0287 (9)
C28	0.4834 (6)	0.0230 (3)	1.04913 (17)	0.0392 (11)
H28A	0.5551	−0.0095	1.0108	0.059*
H28B	0.3594	−0.001	1.0485	0.059*
H28C	0.5368	0.0125	1.099	0.059*

	U11	U22	U33	U12	U13	U23
S1	0.0329 (6)	0.0275 (4)	0.0166 (3)	−0.0011 (5)	−0.0012 (4)	−0.0023 (3)
S2	0.0443 (6)	0.0259 (5)	0.0175 (3)	−0.0023 (5)	−0.0008 (3)	0.0001 (4)
O1	0.084 (3)	0.0299 (14)	0.0212 (9)	−0.0002 (16)	−0.0042 (15)	−0.0037 (9)
O2	0.0500 (19)	0.0330 (13)	0.0189 (9)	0.0006 (14)	0.0028 (12)	0.0030 (9)
O3	0.053 (2)	0.0289 (15)	0.0253 (11)	−0.0018 (13)	−0.0031 (12)	−0.0013 (10)
O4	0.047 (2)	0.0387 (16)	0.0253 (10)	0.0049 (14)	−0.0123 (11)	0.0070 (11)
C1	0.028 (2)	0.0275 (19)	0.0195 (12)	−0.0018 (19)	0.0011 (14)	0.0010 (12)
C2	0.033 (2)	0.027 (2)	0.0193 (12)	0.0011 (19)	−0.0009 (16)	−0.0032 (12)
C3	0.029 (3)	0.027 (2)	0.0224 (14)	−0.002 (2)	−0.0004 (14)	0.0007 (11)
C4	0.035 (2)	0.031 (2)	0.0182 (12)	0.005 (2)	−0.0012 (14)	0.0028 (13)
C11	0.019 (2)	0.032 (2)	0.0186 (13)	0.001 (2)	−0.0006 (14)	−0.0067 (12)
C12	0.026 (2)	0.0257 (18)	0.0211 (13)	0.0007 (18)	0.0009 (15)	−0.0021 (12)
C13	0.033 (3)	0.034 (2)	0.0190 (12)	0.001 (2)	0.0014 (14)	−0.0066 (13)
C14	0.045 (3)	0.034 (2)	0.0265 (14)	0.002 (2)	−0.0003 (18)	−0.0135 (14)
C15	0.039 (3)	0.0284 (18)	0.0339 (14)	0.0011 (19)	0.0039 (19)	−0.0061 (13)
C16	0.039 (3)	0.0237 (19)	0.0223 (13)	0.000 (2)	−0.0014 (16)	0.0005 (12)
C17	0.028 (3)	0.034 (2)	0.0207 (14)	−0.003 (2)	−0.0004 (16)	0.0007 (13)
C18	0.049 (3)	0.038 (2)	0.0294 (14)	−0.002 (2)	−0.0001 (18)	0.0080 (13)
C21	0.029 (2)	0.027 (2)	0.0190 (13)	0.0006 (18)	0.0024 (13)	−0.0059 (14)
C22	0.026 (3)	0.030 (2)	0.0235 (16)	0.0050 (17)	0.0031 (14)	0.0010 (13)
C23	0.028 (2)	0.036 (2)	0.0275 (15)	0.0040 (18)	−0.0051 (15)	−0.0031 (17)
C24	0.039 (3)	0.036 (2)	0.0298 (16)	−0.0001 (19)	−0.0028 (17)	−0.0144 (17)
C25	0.035 (3)	0.026 (2)	0.0343 (16)	−0.0007 (17)	0.0052 (19)	−0.0028 (16)
C26	0.038 (3)	0.029 (2)	0.0214 (14)	−0.0001 (19)	0.0012 (15)	0.0031 (15)
C27	0.030 (3)	0.036 (2)	0.0202 (14)	0.005 (2)	0.0016 (15)	0.0023 (15)
C28	0.050 (3)	0.035 (2)	0.0326 (18)	0.005 (2)	−0.0053 (17)	0.0124 (15)

S1—C11	1.780 (3)	C13—C14	1.360 (5)
S1—C1	1.821 (3)	C13—H13	0.95
S2—C21	1.773 (3)	C14—C15	1.395 (4)
S2—C4	1.822 (3)	C14—H14	0.95
O1—C17	1.211 (4)	C15—C16	1.389 (4)
O2—C17	1.344 (3)	C15—H15	0.95
O2—C18	1.445 (4)	C16—H16	0.95
O3—C27	1.215 (4)	C18—H18A	0.98
O4—C27	1.352 (4)	C18—H18B	0.98
O4—C28	1.454 (4)	C18—H18C	0.98
C1—C2	1.538 (4)	C21—C26	1.380 (5)
C1—H1A	0.99	C21—C22	1.416 (4)
C1—H1B	0.99	C22—C23	1.395 (4)
C2—C3	1.529 (3)	C22—C27	1.465 (5)
C2—H2A	0.99	C23—C24	1.379 (5)
C2—H2B	0.99	C23—H23	0.95
C3—C4	1.526 (4)	C24—C25	1.392 (4)
C3—H3A	0.99	C24—H24	0.95
C3—H3B	0.99	C25—C26	1.395 (5)
C4—H4A	0.99	C25—H25	0.95
C4—H4B	0.99	C26—H26	0.95
C11—C16	1.379 (5)	C28—H28A	0.98
C11—C12	1.421 (4)	C28—H28B	0.98
C12—C13	1.404 (4)	C28—H28C	0.98
C12—C17	1.474 (4)
C11—S1—C1	102.59 (14)	C16—C15—H15	120.3
C21—S2—C4	102.96 (15)	C14—C15—H15	120.3
C17—O2—C18	115.6 (2)	C11—C16—C15	122.0 (3)
C27—O4—C28	115.1 (3)	C11—C16—H16	119
C2—C1—S1	107.3 (2)	C15—C16—H16	119
C2—C1—H1A	110.3	O1—C17—O2	121.9 (3)
S1—C1—H1A	110.3	O1—C17—C12	124.8 (2)
C2—C1—H1B	110.3	O2—C17—C12	113.3 (3)
S1—C1—H1B	110.3	O2—C18—H18A	109.5
H1A—C1—H1B	108.5	O2—C18—H18B	109.5
C3—C2—C1	111.1 (2)	H18A—C18—H18B	109.5
C3—C2—H2A	109.4	O2—C18—H18C	109.5
C1—C2—H2A	109.4	H18A—C18—H18C	109.5
C3—C2—H2B	109.4	H18B—C18—H18C	109.5
C1—C2—H2B	109.4	C26—C21—C22	118.3 (3)
H2A—C2—H2B	108	C26—C21—S2	121.2 (2)
C4—C3—C2	110.5 (2)	C22—C21—S2	120.5 (3)
C4—C3—H3A	109.5	C23—C22—C21	119.4 (3)
C2—C3—H3A	109.5	C23—C22—C27	119.8 (3)
C4—C3—H3B	109.5	C21—C22—C27	120.8 (3)
C2—C3—H3B	109.5	C24—C23—C22	121.4 (3)
H3A—C3—H3B	108.1	C24—C23—H23	119.3
C3—C4—S2	106.9 (2)	C22—C23—H23	119.3
C3—C4—H4A	110.3	C23—C24—C25	119.4 (3)
S2—C4—H4A	110.3	C23—C24—H24	120.3
C3—C4—H4B	110.3	C25—C24—H24	120.3
S2—C4—H4B	110.3	C24—C25—C26	119.5 (3)
H4A—C4—H4B	108.6	C24—C25—H25	120.2
C16—C11—C12	118.3 (3)	C26—C25—H25	120.2
C16—C11—S1	121.6 (2)	C21—C26—C25	121.9 (3)
C12—C11—S1	120.1 (3)	C21—C26—H26	119
C13—C12—C11	118.8 (3)	C25—C26—H26	119
C13—C12—C17	119.8 (3)	O3—C27—O4	120.9 (3)
C11—C12—C17	121.4 (3)	O3—C27—C22	125.5 (3)
C14—C13—C12	121.7 (3)	O4—C27—C22	113.6 (3)
C14—C13—H13	119.2	O4—C28—H28A	109.5
C12—C13—H13	119.2	O4—C28—H28B	109.5
C13—C14—C15	119.8 (3)	H28A—C28—H28B	109.5
C13—C14—H14	120.1	O4—C28—H28C	109.5
C15—C14—H14	120.1	H28A—C28—H28C	109.5
C16—C15—C14	119.4 (3)	H28B—C28—H28C	109.5
C11—S1—C1—C2	177.5 (3)	C13—C12—C17—O2	2.0 (6)
S1—C1—C2—C3	−178.5 (3)	C11—C12—C17—O2	−176.6 (4)
C1—C2—C3—C4	176.1 (4)	C4—S2—C21—C26	7.4 (4)
C2—C3—C4—S2	−176.2 (3)	C4—S2—C21—C22	−171.7 (3)
C21—S2—C4—C3	168.3 (3)	C26—C21—C22—C23	−0.9 (6)
C1—S1—C11—C16	2.2 (4)	S2—C21—C22—C23	178.2 (3)
C1—S1—C11—C12	−178.1 (4)	C26—C21—C22—C27	179.2 (4)
C16—C11—C12—C13	−1.6 (7)	S2—C21—C22—C27	−1.6 (5)
S1—C11—C12—C13	178.7 (3)	C21—C22—C23—C24	0.3 (6)
C16—C11—C12—C17	177.0 (4)	C27—C22—C23—C24	−179.9 (4)
S1—C11—C12—C17	−2.7 (6)	C22—C23—C24—C25	−0.1 (6)
C11—C12—C13—C14	1.0 (7)	C23—C24—C25—C26	0.5 (6)
C17—C12—C13—C14	−177.6 (4)	C22—C21—C26—C25	1.3 (6)
C12—C13—C14—C15	0.9 (7)	S2—C21—C26—C25	−177.8 (3)
C13—C14—C15—C16	−2.2 (7)	C24—C25—C26—C21	−1.2 (6)
C12—C11—C16—C15	0.3 (7)	C28—O4—C27—O3	1.6 (5)
S1—C11—C16—C15	−180.0 (3)	C28—O4—C27—C22	−179.1 (3)
C14—C15—C16—C11	1.6 (7)	C23—C22—C27—O3	177.5 (3)
C18—O2—C17—O1	−4.3 (6)	C21—C22—C27—O3	−2.7 (7)
C18—O2—C17—C12	174.2 (4)	C23—C22—C27—O4	−1.8 (6)
C13—C12—C17—O1	−179.6 (4)	C21—C22—C27—O4	178.1 (3)
C11—C12—C17—O1	1.8 (7)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O2	0.95	2.36	2.705 (4)	101
C23—H23···O4	0.95	2.35	2.701 (5)	101
C15—H15···O3i	0.95	2.45	3.123 (5)	127

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15⋯O3i	0.95	2.45	3.123 (5)	127

Symmetry code: (i) .