Bis[2-(1,3-benzothia-zol-2-ylsulfan-yl)eth-yl] ether.

The complete molecule of title compound, C(18)H(16)N(2)OS(4), is generated by crystallographic twofold symmetry, with the O atom lying on the rotation axis. The dihedral angle between the ring systems is 80.91 (2)°. In the crystal, adjacent mol-ecules are connected through π-π stacking inter-actions [centroid-centroid distance = 3.882 (2) Å], forming a three-dimensional network.

Related literature

For coordination polymers in supra­molecular chemistry and crystal engineering, see: Robinson & Zaworotko (1995 ▶); Yaghi & Li (1996 ▶); Fujita et al. (1995 ▶); Tong et al. (2000 ▶); Bu et al. (2003 ▶); Long et al. (2004 ▶); Massue et al. (2007 ▶); Zou et al. (2004 ▶).

Experimental

Crystal data

C18H16N2OS4

M = 404.57

Monoclinic,

a = 24.617 (3) Å

b = 4.7085 (3) Å

c = 17.7866 (15) Å

β = 116.571 (13)°

V = 1843.9 (3) Å3

Z = 4

Cu Kα radiation

μ = 4.81 mm−1

T = 293 K

0.18 × 0.15 × 0.07 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2005 ▶) T min = 0.765, T max = 1.000

2930 measured reflections

1682 independent reflections

1353 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.129

S = 1.05

1682 reflections

114 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.25 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2005 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2005 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809052301/ng2684sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809052301/ng2684Isup2.hkl

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

C18H16N2OS4	F(000) = 840
Mr = 404.57	Dx = 1.457 Mg m−3
Monoclinic, C2/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -C 2yc	Cell parameters from 1595 reflections
a = 24.617 (3) Å	θ = 2.8–68.1°
b = 4.7085 (3) Å	µ = 4.81 mm−1
c = 17.7866 (15) Å	T = 293 K
β = 116.571 (13)°	Block, colourless
V = 1843.9 (3) Å3	0.18 × 0.15 × 0.07 mm
Z = 4

Oxford Diffraction Xcalibur Sapphire3 diffractometer	1682 independent reflections
Radiation source: Enhance (Cu) X-ray Source	1353 reflections with I > 2σ(I)
graphite	Rint = 0.020
Detector resolution: 16.0855 pixels mm-1	θmax = 68.1°, θmin = 2.8°
ω scans	h = −29→25
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2005)	k = −5→3
Tmin = 0.765, Tmax = 1.000	l = −21→19
2930 measured reflections

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: inferred from neighbouring sites
wR(F2) = 0.129	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0876P)2] where P = (Fo2 + 2Fc2)/3
1682 reflections	(Δ/σ)max = 0.001
114 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.25 e Å−3

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	0.17154 (13)	0.1689 (5)	1.11310 (16)	0.0505 (6)
C2	0.18584 (15)	−0.0249 (6)	1.17798 (17)	0.0608 (7)
H2	0.2256	−0.0860	1.2098	0.073*
C3	0.13924 (18)	−0.1235 (7)	1.1936 (2)	0.0701 (8)
H3	0.1474	−0.2568	1.2359	0.084*
C4	0.08011 (16)	−0.0269 (8)	1.1470 (2)	0.0702 (8)
H4	0.0494	−0.0954	1.1591	0.084*
C5	0.06625 (15)	0.1676 (6)	1.0837 (2)	0.0614 (7)
H5	0.0266	0.2328	1.0534	0.074*
C6	0.11236 (12)	0.2665 (6)	1.06519 (15)	0.0489 (6)
C7	0.15597 (12)	0.4948 (6)	0.99910 (14)	0.0483 (6)
C8	0.09486 (13)	0.8627 (6)	0.86818 (16)	0.0532 (6)
H8C	0.0791	0.9199	0.9070	0.064*
H8B	0.0995	1.0323	0.8406	0.064*
C9	0.05001 (13)	0.6678 (5)	0.80325 (17)	0.0552 (6)
H9A	0.0683	0.5769	0.7712	0.066*
H9B	0.0370	0.5215	0.8300	0.066*
N1	0.10483 (10)	0.4522 (5)	1.00023 (13)	0.0507 (5)
S1	0.21965 (3)	0.32443 (16)	1.07717 (4)	0.0560 (2)
S2	0.16852 (3)	0.69930 (17)	0.92661 (4)	0.0592 (3)
O1	0.0000	0.8363 (5)	0.7500	0.0501 (6)

	U11	U22	U33	U12	U13	U23
C1	0.0535 (14)	0.0516 (13)	0.0422 (12)	−0.0026 (11)	0.0176 (11)	−0.0037 (10)
C2	0.0671 (18)	0.0625 (16)	0.0465 (14)	0.0052 (13)	0.0197 (13)	0.0058 (12)
C3	0.094 (2)	0.0659 (17)	0.0546 (16)	−0.0017 (16)	0.0364 (17)	0.0077 (13)
C4	0.081 (2)	0.076 (2)	0.0661 (18)	−0.0114 (16)	0.0442 (17)	−0.0024 (15)
C5	0.0579 (16)	0.0686 (18)	0.0606 (17)	−0.0045 (13)	0.0290 (14)	−0.0061 (13)
C6	0.0530 (15)	0.0504 (13)	0.0395 (12)	−0.0021 (11)	0.0171 (11)	−0.0063 (10)
C7	0.0454 (13)	0.0524 (13)	0.0387 (11)	−0.0023 (10)	0.0112 (10)	−0.0007 (10)
C8	0.0561 (15)	0.0484 (13)	0.0442 (13)	0.0012 (11)	0.0127 (11)	0.0024 (10)
C9	0.0528 (15)	0.0482 (13)	0.0482 (13)	0.0051 (11)	0.0078 (12)	−0.0003 (11)
N1	0.0460 (11)	0.0559 (12)	0.0427 (10)	−0.0030 (9)	0.0132 (9)	−0.0023 (9)
S1	0.0438 (4)	0.0679 (5)	0.0484 (4)	0.0033 (3)	0.0136 (3)	0.0090 (3)
S2	0.0450 (4)	0.0713 (5)	0.0519 (4)	−0.0050 (3)	0.0132 (3)	0.0131 (3)
O1	0.0485 (14)	0.0462 (13)	0.0436 (12)	0.000	0.0099 (11)	0.000

C1—C2	1.387 (4)	C7—N1	1.284 (4)
C1—C6	1.396 (4)	C7—S2	1.744 (3)
C1—S1	1.739 (3)	C7—S1	1.755 (3)
C2—C3	1.376 (5)	C8—C9	1.501 (4)
C2—H2	0.9300	C8—S2	1.810 (3)
C3—C4	1.390 (5)	C8—H8C	0.9700
C3—H3	0.9300	C8—H8B	0.9700
C4—C5	1.372 (5)	C9—O1	1.414 (3)
C4—H4	0.9300	C9—H9A	0.9700
C5—C6	1.395 (4)	C9—H9B	0.9700
C5—H5	0.9300	O1—C9i	1.414 (3)
C6—N1	1.394 (4)
C2—C1—C6	122.1 (3)	N1—C7—S1	116.8 (2)
C2—C1—S1	128.4 (2)	S2—C7—S1	116.50 (15)
C6—C1—S1	109.5 (2)	C9—C8—S2	112.65 (19)
C3—C2—C1	117.7 (3)	C9—C8—H8C	109.1
C3—C2—H2	121.1	S2—C8—H8C	109.1
C1—C2—H2	121.1	C9—C8—H8B	109.1
C2—C3—C4	121.0 (3)	S2—C8—H8B	109.1
C2—C3—H3	119.5	H8C—C8—H8B	107.8
C4—C3—H3	119.5	O1—C9—C8	107.0 (2)
C5—C4—C3	121.1 (3)	O1—C9—H9A	110.3
C5—C4—H4	119.4	C8—C9—H9A	110.3
C3—C4—H4	119.4	O1—C9—H9B	110.3
C4—C5—C6	119.1 (3)	C8—C9—H9B	110.3
C4—C5—H5	120.4	H9A—C9—H9B	108.6
C6—C5—H5	120.4	C7—N1—C6	110.1 (2)
N1—C6—C5	125.7 (2)	C1—S1—C7	88.23 (13)
N1—C6—C1	115.3 (2)	C7—S2—C8	101.30 (13)
C5—C6—C1	118.9 (3)	C9—O1—C9i	111.7 (3)
N1—C7—S2	126.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O1ii	0.93	2.71	3.358 (3)	128