Dimethyl 2,2'-[ethane-1,2-diylbis(sulfanedi-yl)]dibenzoate.

The title compound, C(18)H(18)O(4)S(2), was synthesized by the reaction of 1,2-dibromo-ethane with methyl thio-salicylate. The complete molecule is generated by crystallographic twofold symmetry: two methyl benzoate units are linked by an -S-(CH(2))(2)-S- bridging chain with a gauche S-CH(2)-CH(2)-S torsion angle [72.88 (16)°]. The two aromatic rings form a dihedral angle of 79.99 (6)°. In the crystal, adjacent mol-ecules are linked into a three-dimensional network by non-classical C-H⋯O hydrogen bonds.

Related literature

For the potential use of dithiodibenzoates in the construction of diverse frameworks with tailored properties and functions, see: Humphrey et al. (2004 ▶); Li et al. (2007 ▶); Murugavel et al. (2001 ▶); Wang et al. (2004 ▶); Zhou et al. (2009 ▶).

Experimental

Crystal data

C18H18O4S2

M = 362.44

Monoclinic,

a = 15.077 (3) Å

b = 5.3913 (10) Å

c = 12.495 (2) Å

β = 120.662 (2)°

V = 873.6 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.32 mm−1

T = 296 K

0.52 × 0.32 × 0.22 mm

Data collection

Bruker SMART APEXII diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2006 ▶) T min = 0.850, T max = 0.932

3836 measured reflections

1948 independent reflections

1864 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.082

S = 1.08

1948 reflections

110 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.15 e Å−3

Absolute structure: Flack (1983 ▶), 834 Friedel pairs

Flack parameter: −0.02 (7)

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg, 2000 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810022403/jh2166sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810022403/jh2166Isup2.hkl

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

C18H18O4S2	F(000) = 380
Mr = 362.44	Dx = 1.378 Mg m−3
Monoclinic, C2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2y	Cell parameters from 2178 reflections
a = 15.077 (3) Å	θ = 2.7–27.4°
b = 5.3913 (10) Å	µ = 0.32 mm−1
c = 12.495 (2) Å	T = 296 K
β = 120.662 (2)°	Block, colourless
V = 873.6 (3) Å3	0.52 × 0.32 × 0.22 mm
Z = 2

Bruker SMART APEXII diffractometer	1948 independent reflections
Radiation source: fine-focus sealed tube	1864 reflections with I > 2σ(I)
graphite	Rint = 0.023
ω scans	θmax = 27.5°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2006)	h = −19→18
Tmin = 0.850, Tmax = 0.932	k = −6→6
3836 measured reflections	l = −16→16

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)] = 0.032	H-atom parameters constrained
wR(F2) = 0.082	w = 1/[σ2(Fo2) + (0.0441P)2 + 0.1272P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max < 0.001
1948 reflections	Δρmax = 0.23 e Å−3
110 parameters	Δρmin = −0.15 e Å−3
1 restraint	Absolute structure: Flack (1983), 834 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.02 (7)

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
C1	0.24609 (11)	0.0317 (4)	0.17607 (14)	0.0440 (3)
C2	0.31876 (12)	0.1986 (4)	0.26461 (15)	0.0455 (4)
C3	0.42223 (14)	0.1865 (5)	0.29514 (18)	0.0590 (5)
H3	0.4700	0.2970	0.3530	0.071*
C4	0.45387 (16)	0.0121 (6)	0.2402 (2)	0.0689 (7)
H4	0.5224	0.0062	0.2606	0.083*
C5	0.38363 (18)	−0.1516 (5)	0.1556 (2)	0.0694 (7)
H5	0.4051	−0.2695	0.1192	0.083*
C6	0.28109 (16)	−0.1440 (4)	0.12343 (19)	0.0577 (5)
H6	0.2348	−0.2574	0.0660	0.069*
C7	0.28831 (13)	0.3846 (4)	0.32683 (16)	0.0478 (4)
C8	0.05804 (14)	−0.2095 (4)	0.02558 (17)	0.0525 (4)
H8A	0.0717	−0.1916	−0.0420	0.063*
H8B	0.0879	−0.3649	0.0679	0.063*
C9	0.3458 (2)	0.6901 (7)	0.4813 (3)	0.0898 (8)
H9A	0.2859	0.7821	0.4230	0.135*
H9B	0.4035	0.8008	0.5233	0.135*
H9C	0.3330	0.6119	0.5411	0.135*
O1	0.36822 (11)	0.5052 (4)	0.41658 (15)	0.0793 (5)
O2	0.20111 (11)	0.4248 (3)	0.30111 (15)	0.0675 (4)
S1	0.11495 (3)	0.04719 (7)	0.13359 (4)	0.04790 (14)

	U11	U22	U33	U12	U13	U23
C1	0.0394 (7)	0.0510 (9)	0.0398 (7)	0.0110 (9)	0.0188 (6)	0.0069 (9)
C2	0.0355 (8)	0.0578 (11)	0.0388 (8)	0.0087 (7)	0.0157 (7)	0.0098 (7)
C3	0.0380 (9)	0.0805 (14)	0.0535 (10)	0.0051 (9)	0.0198 (8)	0.0137 (10)
C4	0.0461 (10)	0.100 (2)	0.0675 (12)	0.0304 (14)	0.0340 (9)	0.0303 (14)
C5	0.0659 (14)	0.0845 (17)	0.0697 (14)	0.0365 (12)	0.0433 (12)	0.0199 (12)
C6	0.0567 (11)	0.0623 (12)	0.0551 (11)	0.0187 (10)	0.0292 (9)	0.0041 (9)
C7	0.0387 (9)	0.0555 (11)	0.0409 (8)	−0.0024 (8)	0.0143 (7)	0.0010 (8)
C8	0.0529 (10)	0.0413 (9)	0.0474 (10)	0.0051 (8)	0.0141 (8)	−0.0028 (7)
C9	0.0861 (18)	0.0898 (19)	0.0753 (16)	−0.0203 (16)	0.0279 (14)	−0.0349 (16)
O1	0.0477 (7)	0.1046 (15)	0.0671 (8)	−0.0113 (9)	0.0159 (6)	−0.0323 (10)
O2	0.0418 (7)	0.0789 (10)	0.0765 (9)	−0.0027 (7)	0.0264 (7)	−0.0284 (8)
S1	0.03542 (19)	0.0520 (2)	0.0488 (2)	0.0033 (2)	0.01601 (15)	−0.0082 (2)

C1—C6	1.401 (3)	C6—H6	0.9300
C1—C2	1.413 (3)	C7—O2	1.203 (2)
C1—S1	1.7685 (15)	C7—O1	1.324 (2)
C2—C3	1.406 (2)	C8—C8i	1.527 (4)
C2—C7	1.478 (3)	C8—S1	1.8143 (19)
C3—C4	1.384 (4)	C8—H8A	0.9700
C3—H3	0.9300	C8—H8B	0.9700
C4—C5	1.370 (4)	C9—O1	1.429 (3)
C4—H4	0.9300	C9—H9A	0.9600
C5—C6	1.386 (3)	C9—H9B	0.9600
C5—H5	0.9300	C9—H9C	0.9600
C6—C1—C2	118.08 (15)	O2—C7—O1	122.42 (19)
C6—C1—S1	121.47 (16)	O2—C7—C2	124.88 (16)
C2—C1—S1	120.44 (14)	O1—C7—C2	112.71 (16)
C3—C2—C1	119.52 (18)	C8i—C8—S1	108.52 (12)
C3—C2—C7	119.22 (18)	C8i—C8—H8A	110.0
C1—C2—C7	121.26 (14)	S1—C8—H8A	110.0
C4—C3—C2	120.8 (2)	C8i—C8—H8B	110.0
C4—C3—H3	119.6	S1—C8—H8B	110.0
C2—C3—H3	119.6	H8A—C8—H8B	108.4
C5—C4—C3	119.61 (18)	O1—C9—H9A	109.5
C5—C4—H4	120.2	O1—C9—H9B	109.5
C3—C4—H4	120.2	H9A—C9—H9B	109.5
C4—C5—C6	120.9 (2)	O1—C9—H9C	109.5
C4—C5—H5	119.5	H9A—C9—H9C	109.5
C6—C5—H5	119.5	H9B—C9—H9C	109.5
C5—C6—C1	121.0 (2)	C7—O1—C9	116.51 (17)
C5—C6—H6	119.5	C1—S1—C8	102.68 (10)
C1—C6—H6	119.5
C6—C1—C2—C3	1.1 (3)	S1—C1—C6—C5	178.76 (16)
S1—C1—C2—C3	−178.69 (15)	C3—C2—C7—O2	173.83 (19)
C6—C1—C2—C7	−178.26 (18)	C1—C2—C7—O2	−6.8 (3)
S1—C1—C2—C7	1.9 (2)	C3—C2—C7—O1	−6.6 (3)
C1—C2—C3—C4	−0.4 (3)	C1—C2—C7—O1	172.80 (18)
C7—C2—C3—C4	178.97 (18)	O2—C7—O1—C9	−0.9 (3)
C2—C3—C4—C5	−0.4 (3)	C2—C7—O1—C9	179.6 (2)
C3—C4—C5—C6	0.5 (3)	C6—C1—S1—C8	2.60 (18)
C4—C5—C6—C1	0.3 (3)	C2—C1—S1—C8	−177.58 (15)
C2—C1—C6—C5	−1.1 (3)	C8i—C8—S1—C1	−176.60 (15)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1	0.93	2.34	2.679 (3)	101
C4—H4···O2ii	0.93	2.51	3.435 (2)	171

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O2i	0.93	2.51	3.435 (2)	171

Symmetry code: (i) .