(1Z,2E)-1-(3,4-Diphenyl-2,3-di­hydro-1,3-thia­zol-2-yl­idene)-2-(1-p-tolyl­ethyl­idene)hydrazine

Shaaban K Mohamed; Joel T Mague; Mehmet Akkurt; Alaa A Hassan; Mustafa R Albayati

doi:10.1107/S1600536813020254

. 2013 Jul 27;69(Pt 8):o1324. doi: 10.1107/S1600536813020254

(1Z,2E)-1-(3,4-Diphenyl-2,3-dihydro-1,3-thiazol-2-ylidene)-2-(1-p-tolylethylidene)hydrazine

Shaaban K Mohamed ^a,^b, Joel T Mague ^c, Mehmet Akkurt ^d, Alaa A Hassan ^b, Mustafa R Albayati ^e,^*

PMCID: PMC3793809 PMID: 24109396

Abstract

In the title compound, C₂₄H₂₁N₃S, the thiazole ring makes dihedral angles of 52.03 (6), 62.63 (6) and 12.35 (6)°, respectively, with the two phenyl rings and the benzene ring. In the crystal, weak C—H⋯π interactions occur between inversion-related molecules.

Related literature

For the syntheses and bioactivity of thiazole-containing compounds, see: Siddiqui et al. (2009 ▶); Ramla et al. (2006 ▶); Popsavin et al. (2007 ▶); Kumar et al. (2007 ▶); Pandeya et al. (1999 ▶); Narayana et al. (2004 ▶); Shiradkar et al. (2007 ▶); Amin et al. (2008 ▶); Shih & Ying (2004 ▶); Andreani et al. (1987 ▶). graphic file with name e-69-o1324-scheme1.jpg

Experimental

Crystal data

C₂₄H₂₁N₃S
M _r = 383.51
Triclinic,
a = 7.9370 (8) Å
b = 10.7587 (11) Å
c = 11.9325 (13) Å
α = 94.922 (2)°
β = 97.436 (2)°
γ = 95.383 (2)°
V = 1000.95 (18) Å³
Z = 2
Mo Kα radiation
μ = 0.18 mm⁻¹
T = 150 K
0.30 × 0.15 × 0.12 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2013 ▶) T _min = 0.83, T _max = 0.98
17908 measured reflections
4870 independent reflections
4287 reflections with I > 2σ(I)
R _int = 0.034

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.119
S = 1.06
4870 reflections
255 parameters
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Data collection: APEX2 (Bruker, 2013 ▶); cell refinement: SAINT (Bruker, 2013 ▶); data reduction: SAINT; 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, 2012 ▶) and DIAMOND (Brandenburg & Putz, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813020254/xu5722sup1.cif

e-69-o1324-sup1.cif^{(28.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813020254/xu5722Isup2.hkl

e-69-o1324-Isup2.hkl^{(267KB, hkl)}

Click here for additional data file.^{(7.7KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813020254/xu5722Isup3.cml

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

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

Cg4 is the centroid of the C18–C23 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15⋯Cg4ⁱ	0.95	2.71	3.6170 (16)	160
C16—H16A⋯Cg4ⁱⁱ	0.98	2.77	3.5984 (16)	143

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

Manchester Metropolitan University, Tulane University and Erciyes University are gratefully acknowledged for supporting this study.

supplementary crystallographic information

Comment

1,3-Thiazole containing compounds are a great class of sulfur heterocyclic molecules due to their vital interest in pharmaceutical and industrial chemistry. Numerous of synthesized active thiazole scaffold molecules having diverse of biologically activities have been reported (Ramla et al., 2006; Popsavin et al., 2007; Kumar et al., 2007; Pandeya et al., 1999; Narayana et al., 2004; Shiradkar et al., 2007; Amin et al., 2008; Shih & Ying, 2004; Andreani et al., 1987). In addition, thiazole compounds have not only found in natural molecules such as Thiamin (vitamin B1) but also have been found in many drugs such as Abafungin (antifungal drug), Bleomycine and Tiazofurin (antineoplastic drug), Ritonavir (antiretroviral drug) and Sulfathiazol (antimicrobial drug) (Siddiqui et al., 2009).

In the title compound (I), (Fig. 1), the (S1/N1/C1–C3) thiazole ring is essentially planar with a maximum deviation of -0.006 (1) Å for C2. The dihedral angles between the thiazole ring, and the phenyl rings (C4–C9 and C10–C15) and the benzene ring (C18—C23) are 52.03 (6), 62.63 (6) and 12.35 (6)°, respectively.

In the crystal structure, the title molecules pack in a layer structure with the layers approximately parallel to [101] and held together by a combination of C—H···S hydrogen bonds (Table 1 and Fig. 2) and C—H···π interactions (Fig. 3: H15···Cg1 = 2.71 Å; C15—H15···Cg1 = 160° and H16a···Cg2 = 2.77 Å; C16—H16a···Cg2 = 143° where Cg1 is the centroid of the ring C18–C23 at 1 - x, 1 - y, 1 - z and Cg2 is the centroid of the ring C18–C23 at 2 - x, 1 - y, 1 - z).

Experimental

A solution of 283 mg (1 mmol) (2E)-2-[1-(4-methylphenyl)ethylidene]-N-phenylhydrazinecarbothioamide in 15 ml e thanol was added dropwise to a solution of 199 mg (1 mmol) 2-bromo-1-phenylethanone in 20 ml e thanol and few drops of piperidine. The reaction mixture was stirred and refluxed for 6 h. On cooling the solid product was precipitated, filtered off and recrystallized from ethanol to furnish translucent yellow blocks (M.p. 509 - 511 K) suitable for X-ray diffraction.

IR [ν, cm^-1,KBr]: 3052 (Ar—CH), 2941, 2863 (Ali – CH), 1594 (Ar—C=C), 1350(C=S); ¹H– NMR [δ, p.p.m., CDCl₃]: 1.26, 1.65, 1.94 and 2.20 (10H, cyclohexane – CH₂), 7.707,7.51, 7.55 (SH, Ar –H); ¹³C–NMR [δ, p.p.m., CDCl₃]: 23.58, 24.52 and 33.90 (cyclohexane- CH₂), 112.19 (spiro Cx b), 127.81, 129.87, 130.22 (Ar- CH), 135.07 (Ar-c), 187.83 (C=S).