N-(2-Thienylmethyl­ene)-2-(2-{[2-(2-thienylmethyl­eneamino)phen­yl]sulfan­yl}ethyl­sulfan­yl)aniline

Ali Kakanejadifard; Vahid Amani

doi:10.1107/S1600536809024404

. 2009 Jun 27;65(Pt 7):o1712. doi: 10.1107/S1600536809024404

N-(2-Thienylmethylene)-2-(2-{[2-(2-thienylmethyleneamino)phenyl]sulfanyl}ethylsulfanyl)aniline

Ali Kakanejadifard ^a,^*, Vahid Amani ^b

PMCID: PMC2969378 PMID: 21582963

Abstract

The asymmetric unit of the title compound, C₂₄H₂₀N₂S₄, contains one half-molecule: a crystallographic centre of inversion is located at the mid-point of the two central C atoms. The thiophene ring is oriented at a dihedral angle of 60.64 (3)° with respect to the benzene ring. In the crystal structure, π–π contacts between thiophene rings [centroid–centroid distance = 3.581 (1) Å] may stabilize the structure. A weak C—H⋯π interaction is also present.

Related literature

For related structures, see: Dharaa et al. (2005 ▶); Gok & Demirbas (1989 ▶); Kakanejadifard et al. (2007 ▶); Kakanejadifard & Amani (2008 ▶); Morshedi et al. (2009 ▶); Rajsekhar et al. (2002 ▶, 2004 ▶); Taylor et al. (2008 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₂₄H₂₀N₂S₄
M _r = 464.66
Monoclinic,
a = 11.179 (5) Å
b = 7.730 (4) Å
c = 12.608 (6) Å
β = 91.899 (12)°
V = 1088.9 (9) Å³
Z = 2
Mo Kα radiation
μ = 0.45 mm⁻¹
T = 100 K
0.30 × 0.20 × 0.15 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.895, T _max = 0.930
12880 measured reflections
2899 independent reflections
2569 reflections with I > 2/s(I)
R _int = 0.029

Refinement

R[F ² > 2σ(F ²)] = 0.029
wR(F ²) = 0.079
S = 1.00
2899 reflections
136 parameters
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809024404/hk2716sup1.cif

e-65-o1712-sup1.cif^{(15.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809024404/hk2716Isup2.hkl

e-65-o1712-Isup2.hkl^{(142.3KB, hkl)}

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10A⋯Cg1ⁱ	0.95	2.80	3.740 (3)	171

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Symmetry code: (i) Inline graphic . Cg1 is centroid of the ring C2–C7 ring.

Acknowledgments

We are grateful to the Research Grant Council of Lorestan University for financial support.

supplementary crystallographic information

Comment

There are several examples of N₂S₂ Schiff bases type of adducts which exist as anti configuration. For 2-[2-(2-aminophenylthio)benzeneamine] adduct see: (Gok & Demirbas, 1989; Dharaa et al., 2005; Kakanejadifard et al., 2007; Kakanejadifard & Amani, 2008). For N₂S₂ Schiff bases adduct see: (Rajsekhar et al., 2002; Taylor et al., 2008; Morshedi et al., 2009). For N₂O₂S₂ Schiff bases adduct see: (Rajsekhar et al., 2004). We report herein the synthesis and crystal structure of the title compound.

The asymmetric unit of the title compound, (Fig. 1), contains one-half molecule. A crystallographic centre of inversion is located at the midpoint between the two central C atoms. The bond lengths (Allen et al., 1987) and angles are within normal ranges. Rings A (C2-C7) and B (S2/C9-C12) are, of course, planar and they are oriented at a dihedral angle of 60.64 (3)°.

In the crystal structure, the π–π contact between the thiophene rings, Cg2—Cg2ⁱ, [symmetry code: (i) -x, -y, 1 - z, where Cg2 is centroid of the ring B (S2/C9-C12)] may stabilize the structure, with centroid-centroid distance of 3.581 (1) Å. There also exits a weak C—H···π interaction (Table 1).

Experimental

For the preparation of the title compound, a solution of thiophencarbaldehyde (20 mmol) was added dropwise to a solution of 2-[2-(2-aminophenylthio)benzeneamine] (2.76 g, 10 mmol) in absolute ethanol (25 ml) with stirring in 10 min at room temperature. The mixture was stirred and heated to reflux for 5 h. The product was filtered and crystallized from CH₃CN (yield; 45%, m.p. 398-399 K).