(E)-4-(2-Chloro­benzyl­ideneamino)-3-(2-chloro­phen­yl)-1H-1,2,4-triazole-5(4H)-thione–(E)-1,5-bis­(2-chloro­benzyl­idene)thio­carbonohydrazide–methanol (1/1/1)

Qingliang Guo

doi:10.1107/S1600536809053203

. 2009 Dec 16;66(Pt 1):o141. doi: 10.1107/S1600536809053203

(E)-4-(2-Chlorobenzylideneamino)-3-(2-chlorophenyl)-1H-1,2,4-triazole-5(4H)-thione–(E)-1,5-bis(2-chlorobenzylidene)thiocarbonohydrazide–methanol (1/1/1)

Qingliang Guo ^a,^*

PMCID: PMC2980177 PMID: 21580033

Abstract

In the title compound, C₁₅H₁₂Cl₂N₄S·C₁₅H₁₀Cl₂N₄S·C₂H₆O, the two chlorophenyl rings of the triazole derivative form dihedral angles of 65.7 (2) and 44.2 (2)° with the triazole ring. In the thiocarbonohydrazide derivative, the dihedral angle between the two chlorophenyl rings is 5.4 (2)°. In the crystal, the triazole, thiocarbonohydrazide and methanol molecules are linked by N—H⋯O, N—H⋯S and O—H⋯S hydrogen bonds, forming a hexameric unit.

Related literature

For general background to Schiff bases, see: Ren et al. (1999 ▶); Yang et al. (2005 ▶); Sen et al. (1998 ▶); Xia et al. (2007 ▶). For the biological activity of Schiff bases, see: Liang (2003 ▶); Bacci et al. (2005 ▶).

Experimental

Crystal data

C₁₅H₁₀Cl₂N₄S·C₁₅H₁₂Cl₂N₄S·C₂H₆O
M _r = 746.54
Triclinic,
a = 7.7086 (6) Å
b = 10.9999 (9) Å
c = 20.9827 (16) Å
α = 94.678 (1)°
β = 92.083 (1)°
γ = 99.851 (1)°
V = 1744.8 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.50 mm⁻¹
T = 293 K
0.35 × 0.26 × 0.23 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.845, T _max = 0.894
9324 measured reflections
6154 independent reflections
3724 reflections with I > 2σ(I)
R _int = 0.026

Refinement

R[F ² > 2σ(F ²)] = 0.046
wR(F ²) = 0.111
S = 1.01
6154 reflections
425 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Data collection: SMART (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; 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: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809053203/ci2984sup1.cif

e-66-0o141-sup1.cif^{(26.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809053203/ci2984Isup2.hkl

e-66-0o141-Isup2.hkl^{(301.2KB, 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
N2—H2⋯O1	0.86	2.20	2.978 (4)	150
N6—H6⋯S1ⁱ	0.86	2.41	3.261 (3)	170
N3—H3⋯S2ⁱⁱ	0.86	2.56	3.410 (2)	169
O1—H1⋯S1ⁱⁱⁱ	0.82	2.65	3.413 (3)	156

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

Acknowledgments

The author thanks the Postgraduate Foundation of Taishan University for financial support (grant No. Y06-2-10).

supplementary crystallographic information

Comment

The synthesis and structural investigation of Schiff base compounds have attracted much attention due to their interesting structures and potential applications. Some of them have biological activities (Liang, 2003; Bacci et al., 2005). They also play an important role in the development of coordination chemistry as well as inorganic biochemistry, catalysis and optical materials (Ren et al., 1999; Yang et al. 2005; Sen et al. 1998).

The triazole ring forms dihedral angles of 65.7 (2) and 44.2 (2)°, respectively, with the C16-C21 and C25-C30 rings. The dihedral angle between the C1-C6 and C10-C15 rings is 5.4 (2)°. Two triazole, two thiocarbonohydrazide and two methanol molecules are linked by N—H···O, N—H···S and O—H···S hydrogen bonds to form a hexamer.

Experimental

The Schiff base compound was synthesized according to the modified method of Xia et al. (2007). A mixture of (2-chlorophenyl)methanamine and thiourea in methanol (30 ml) was refluxed for 3 h and filtered. The filtrate was placed for sevaral days yielding colourless block-shaped crystals. (yield 79%). Elemental analysis: Calculated for C₃₂H₂₈Cl₄N₈OS₂: C 51.48, H 3.78, N 15.01; found: C 51.51, H 3.49, N 15.13.