1,4-Bis[2-(1,3-benzothia-zol-2-yl)phen-oxy]butane.

The mol-ecule of the title compound, C(30)H(24)N(2)O(2)S(2), adopts a transoid conformation consistent with the inversion centre located at the mid-point of the central C-C single bond, resulting in one half mol-ecule in the asymmetric unit. The dihedral angle between the coplanar benzothia-zole ring system and the benzene ring is 11.06 (7)°. In the crystal structure, mol-ecules are linked by weak inter-molecular π-π inter-actions between thia-zole and benzene rings to form a three-dimensional network.

Related literature

For general background, see: Delmas et al. (2002 ▶); Karalı et al. (2004 ▶); Weinstock et al. (1987 ▶); Chopade et al. (2002 ▶); Di Nunno et al. (2000 ▶); Gökhan et al. (2004 ▶). For related structures, see: Sieroń et al. (1999 ▶); Usman et al. (2003 ▶). For related literature, see: Temel et al. (2008 ▶).

Experimental

Crystal data

C30H24N2O2S2

M = 508.63

Monoclinic,

a = 14.3251 (13) Å

b = 4.8992 (3) Å

c = 17.4954 (17) Å

β = 102.522 (7)°

V = 1198.65 (18) Å3

Z = 2

Mo Kα radiation

μ = 0.26 mm−1

T = 296 K

0.80 × 0.36 × 0.08 mm

Data collection

Stoe IPDSII diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.442, T max = 0.936

14397 measured reflections

2339 independent reflections

1456 reflections with I > 2σ(I)

R int = 0.075

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.069

S = 0.84

2339 reflections

163 parameters

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.19 e Å−3

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); program(s) used to solve structure: SHELXS97 (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 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808002705/hk2423sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808002705/hk2423Isup2.hkl

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

C30H24N2O2S2	F000 = 532
Mr = 508.63	Dx = 1.409 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 14397 reflections
a = 14.3251 (13) Å	θ = 1.7–28.0º
b = 4.8992 (3) Å	µ = 0.26 mm−1
c = 17.4954 (17) Å	T = 296 K
β = 102.522 (7)º	Thin long plate, colorless
V = 1198.65 (18) Å3	0.80 × 0.36 × 0.08 mm
Z = 2

Stoe IPDSII diffractometer	2339 independent reflections
Radiation source: fine-focus sealed tube	1456 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.075
Detector resolution: 6.67 pixels mm-1	θmax = 26.0º
T = 296 K	θmin = 2.4º
ω scans	h = −16→17
Absorption correction: integration(X-RED32; Stoe & Cie, 2002)	k = −6→6
Tmin = 0.442, Tmax = 0.936	l = −21→21
14397 measured reflections

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)] = 0.034	H-atom parameters constrained
wR(F2) = 0.069	w = 1/[σ2(Fo2) + (0.0302P)2] where P = (Fo2 + 2Fc2)/3
S = 0.84	(Δ/σ)max = 0.001
2339 reflections	Δρmax = 0.14 e Å−3
163 parameters	Δρmin = −0.19 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Experimental. 322 frames, detector distance = 100 mm

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	0.15719 (4)	0.95193 (10)	0.66141 (3)	0.05013 (15)
O1	0.18060 (9)	0.6078 (3)	0.54404 (7)	0.0548 (4)
N1	0.33188 (11)	1.0657 (3)	0.72790 (8)	0.0474 (4)
C1	0.17643 (14)	1.1896 (4)	0.73578 (10)	0.0449 (5)
C2	0.11011 (15)	1.3333 (4)	0.76826 (11)	0.0558 (5)
H2	0.0448	1.3057	0.7506	0.067*
C3	0.14437 (17)	1.5159 (4)	0.82685 (12)	0.0610 (6)
H3	0.1015	1.6124	0.8495	0.073*
C4	0.24200 (17)	1.5602 (4)	0.85322 (11)	0.0593 (5)
H4	0.2634	1.6883	0.8923	0.071*
C5	0.30670 (15)	1.4168 (4)	0.82207 (11)	0.0546 (5)
H5	0.3719	1.4453	0.8402	0.066*
C6	0.27417 (14)	1.2284 (4)	0.76311 (10)	0.0454 (5)
C7	0.28134 (13)	0.9108 (4)	0.67424 (10)	0.0420 (4)
C8	0.32640 (13)	0.7109 (4)	0.63100 (10)	0.0421 (4)
C9	0.42400 (14)	0.6654 (4)	0.65603 (11)	0.0524 (5)
H9	0.4582	0.7634	0.6985	0.063*
C10	0.47127 (14)	0.4785 (4)	0.61944 (12)	0.0596 (6)
H10	0.5365	0.4496	0.6375	0.071*
C11	0.42174 (16)	0.3352 (4)	0.55621 (12)	0.0599 (6)
H11	0.4537	0.2111	0.5308	0.072*
C12	0.32498 (16)	0.3741 (4)	0.53009 (11)	0.0545 (5)
H12	0.2917	0.2754	0.4874	0.065*
C13	0.27700 (13)	0.5594 (4)	0.56711 (10)	0.0453 (4)
C14	0.12712 (14)	0.4466 (4)	0.48140 (10)	0.0518 (5)
H14A	0.1321	0.2546	0.4953	0.062*
H14B	0.1517	0.4722	0.4344	0.062*
C15	0.02453 (14)	0.5376 (4)	0.46736 (11)	0.0556 (5)
H15A	−0.0104	0.4565	0.4190	0.067*
H15B	0.0221	0.7342	0.4607	0.067*

	U11	U22	U33	U12	U13	U23
S1	0.0431 (3)	0.0516 (3)	0.0532 (3)	−0.0016 (3)	0.0050 (2)	−0.0062 (2)
O1	0.0427 (8)	0.0624 (9)	0.0539 (8)	0.0000 (6)	−0.0010 (6)	−0.0175 (7)
N1	0.0471 (10)	0.0445 (9)	0.0480 (9)	−0.0022 (8)	0.0044 (7)	−0.0040 (8)
C1	0.0494 (13)	0.0390 (11)	0.0462 (11)	−0.0003 (9)	0.0103 (9)	0.0044 (8)
C2	0.0520 (13)	0.0539 (13)	0.0614 (13)	0.0044 (10)	0.0122 (10)	−0.0004 (10)
C3	0.0730 (16)	0.0560 (14)	0.0575 (12)	0.0126 (11)	0.0215 (10)	−0.0008 (10)
C4	0.0809 (17)	0.0459 (11)	0.0496 (11)	0.0013 (12)	0.0104 (11)	−0.0067 (10)
C5	0.0599 (14)	0.0488 (12)	0.0516 (11)	−0.0042 (10)	0.0041 (9)	−0.0043 (10)
C6	0.0525 (13)	0.0387 (11)	0.0426 (10)	−0.0012 (9)	0.0053 (9)	0.0018 (8)
C7	0.0425 (11)	0.0426 (11)	0.0392 (9)	−0.0024 (9)	0.0053 (8)	0.0031 (8)
C8	0.0421 (12)	0.0410 (11)	0.0421 (10)	−0.0013 (9)	0.0065 (8)	0.0019 (8)
C9	0.0444 (12)	0.0537 (12)	0.0557 (12)	−0.0011 (10)	0.0034 (9)	−0.0036 (9)
C10	0.0443 (12)	0.0659 (15)	0.0670 (13)	0.0061 (11)	0.0087 (10)	−0.0047 (11)
C11	0.0583 (15)	0.0610 (14)	0.0635 (13)	0.0095 (11)	0.0197 (11)	−0.0063 (11)
C12	0.0565 (14)	0.0574 (13)	0.0483 (11)	−0.0001 (10)	0.0087 (9)	−0.0087 (9)
C13	0.0425 (12)	0.0474 (11)	0.0446 (10)	0.0007 (9)	0.0060 (8)	0.0021 (9)
C14	0.0518 (12)	0.0559 (12)	0.0440 (10)	−0.0085 (10)	0.0024 (8)	−0.0065 (9)
C15	0.0510 (13)	0.0652 (13)	0.0452 (11)	−0.0105 (10)	−0.0012 (8)	0.0023 (10)

C1—S1	1.7231 (19)	C9—C10	1.376 (3)
C1—C2	1.398 (3)	C9—H9	0.9300
C1—C6	1.391 (3)	C10—C11	1.371 (3)
C2—C3	1.369 (3)	C10—H10	0.9300
C2—H2	0.9300	C11—C12	1.375 (3)
C3—C4	1.391 (3)	C11—H11	0.9300
C3—H3	0.9300	C12—C13	1.382 (3)
C4—C5	1.367 (3)	C12—H12	0.9300
C4—H4	0.9300	C13—O1	1.373 (2)
C5—C6	1.387 (3)	C14—O1	1.431 (2)
C5—H5	0.9300	C14—C15	1.504 (3)
C6—N1	1.385 (2)	C14—H14A	0.9700
C7—S1	1.7552 (18)	C14—H14B	0.9700
C7—N1	1.299 (2)	C15—C15i	1.511 (4)
C7—C8	1.469 (2)	C15—H15A	0.9700
C8—C9	1.390 (3)	C15—H15B	0.9700
C8—C13	1.399 (2)
C6—C1—C2	120.89 (18)	C11—C10—C9	119.68 (19)
C6—C1—S1	109.65 (14)	C11—C10—H10	120.2
C2—C1—S1	129.46 (16)	C9—C10—H10	120.2
C3—C2—C1	117.9 (2)	C10—C11—C12	120.33 (19)
C3—C2—H2	121.0	C10—C11—H11	119.8
C1—C2—H2	121.0	C12—C11—H11	119.8
C2—C3—C4	121.45 (19)	C11—C12—C13	120.22 (19)
C2—C3—H3	119.3	C11—C12—H12	119.9
C4—C3—H3	119.3	C13—C12—H12	119.9
C5—C4—C3	120.5 (2)	O1—C13—C12	123.13 (17)
C5—C4—H4	119.8	O1—C13—C8	116.46 (16)
C3—C4—H4	119.8	C12—C13—C8	120.41 (18)
C4—C5—C6	119.4 (2)	O1—C14—C15	107.66 (15)
C4—C5—H5	120.3	O1—C14—H14A	110.2
C6—C5—H5	120.3	C15—C14—H14A	110.2
N1—C6—C5	125.23 (18)	O1—C14—H14B	110.2
N1—C6—C1	114.94 (16)	C15—C14—H14B	110.2
C5—C6—C1	119.82 (18)	H14A—C14—H14B	108.5
N1—C7—C8	121.55 (17)	C14—C15—C15i	113.7 (2)
N1—C7—S1	114.57 (13)	C14—C15—H15A	108.8
C8—C7—S1	123.83 (13)	C15i—C15—H15A	108.8
C9—C8—C13	117.81 (17)	C14—C15—H15B	108.8
C9—C8—C7	117.97 (16)	C15i—C15—H15B	108.8
C13—C8—C7	124.20 (17)	H15A—C15—H15B	107.7
C10—C9—C8	121.54 (18)	C7—N1—C6	111.40 (16)
C10—C9—H9	119.2	C13—O1—C14	117.86 (14)
C8—C9—H9	119.2	C1—S1—C7	89.39 (9)
C6—C1—C2—C3	0.9 (3)	C10—C11—C12—C13	0.4 (3)
S1—C1—C2—C3	−179.08 (15)	C11—C12—C13—O1	−179.97 (18)
C1—C2—C3—C4	0.5 (3)	C11—C12—C13—C8	0.6 (3)
C2—C3—C4—C5	−1.4 (3)	C9—C8—C13—O1	179.64 (16)
C3—C4—C5—C6	0.8 (3)	C7—C8—C13—O1	0.9 (3)
C4—C5—C6—N1	−178.41 (18)	C9—C8—C13—C12	−0.9 (3)
C4—C5—C6—C1	0.7 (3)	C7—C8—C13—C12	−179.58 (17)
C2—C1—C6—N1	177.62 (16)	O1—C14—C15—C15i	−69.4 (3)
S1—C1—C6—N1	−2.4 (2)	C8—C7—N1—C6	−177.23 (15)
C2—C1—C6—C5	−1.6 (3)	S1—C7—N1—C6	0.4 (2)
S1—C1—C6—C5	178.43 (14)	C5—C6—N1—C7	−179.52 (17)
N1—C7—C8—C9	8.4 (3)	C1—C6—N1—C7	1.3 (2)
S1—C7—C8—C9	−168.92 (14)	C12—C13—O1—C14	3.6 (3)
N1—C7—C8—C13	−172.87 (18)	C8—C13—O1—C14	−176.95 (16)
S1—C7—C8—C13	9.8 (2)	C15—C14—O1—C13	179.99 (15)
C13—C8—C9—C10	0.2 (3)	C6—C1—S1—C7	2.04 (14)
C7—C8—C9—C10	179.00 (18)	C2—C1—S1—C7	−177.94 (18)
C8—C9—C10—C11	0.8 (3)	N1—C7—S1—C1	−1.44 (14)
C9—C10—C11—C12	−1.1 (3)	C8—C7—S1—C1	176.08 (15)

Cg-Cgi	dcentroids	dperpendicular
Cg1-Cg2i	3.775 (11)	3.515
Cg1-Cg3i	3.7934 (12)	3.59

Table 1

The observed π–π interaction distances (Å) for the title compound.

Cg—Cgi	dcentroids	dperpendicular
Cg1—Cg2i	3.775 (11)	3.515
Cg1—Cg3i	3.7934 (12)	3.59

Cg1, Cg2 and Cg3 are the centroids of atoms S1/N1/C1/C6/C7, (C1–C6) and (C8–C13) rings, respectively. Symmetry code: (i) .