3-[3-Methyl-4-(3-nitro­benzyl­idene­amino)-5-sulfanyl­idene-4,5-dihydro-1H-1,2,4-triazol-1-yl]-1,3-diphenyl­propan-1-one

Yan Gao; Yan Dong

doi:10.1107/S1600536811033587

. 2011 Aug 27;67(Pt 9):o2482. doi: 10.1107/S1600536811033587

3-[3-Methyl-4-(3-nitrobenzylideneamino)-5-sulfanylidene-4,5-dihydro-1H-1,2,4-triazol-1-yl]-1,3-diphenylpropan-1-one

Yan Gao ^a, Yan Dong ^a,^*

PMCID: PMC3200841 PMID: 22059037

Abstract

In the title molecule, C₂₅H₂₁N₅O₃S, the triazole ring forms dihedral angles of 21.4 (2), 61.4 (2) and 102.4 (2)° with the nitrophenyl and two phenyl rings, respectively. In the crystal, weak C—H⋯O hydrogen bonds and π–π interactions between the benzene rings from neighbouring molecules [with a centroid–centroid distance of 3.571 (3) Å] consolidate the crystal packing.

Related literature

For the crystal structures of related 1,2,4-triazole-5(4H)-thione derivatives, see: Al-Tamimi et al. (2010 ▶); Fun et al. (2009 ▶); Gao et al. (2011 ▶); Tan et al. (2010 ▶); Wang et al. (2011 ▶); Zhao et al. (2010 ▶).

Experimental

Crystal data

C₂₅H₂₁N₅O₃S
M _r = 471.53
Triclinic,
a = 9.0991 (10) Å
b = 11.8026 (15) Å
c = 12.0649 (16) Å
α = 70.92 (1)°
β = 73.042 (12)°
γ = 85.883 (13)°
V = 1170.9 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.18 mm⁻¹
T = 113 K
0.20 × 0.18 × 0.10 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T _min = 0.966, T _max = 0.983
15096 measured reflections
5553 independent reflections
3889 reflections with I > 2σ(I)
R _int = 0.031

Refinement

R[F ² > 2σ(F ²)] = 0.034
wR(F ²) = 0.090
S = 0.98
5553 reflections
308 parameters
H-atom parameters constrained
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXTL.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811033587/cv5140sup1.cif

e-67-o2482-sup1.cif^{(23.1KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811033587/cv5140Isup2.hkl

e-67-o2482-Isup2.hkl^{(271.9KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811033587/cv5140Isup3.cml

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
C3—H3⋯O1ⁱ	1.00	2.57	3.4922 (15)	154
C4—H4B⋯O3ⁱⁱ	0.99	2.59	3.5002 (16)	153
C17—H17⋯O1ⁱ	0.95	2.47	3.3076 (15)	147
C25—H25B⋯O3ⁱⁱⁱ	0.98	2.57	3.5310 (18)	168

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

supplementary crystallographic information

Comment

In continuation of structural study of Mannich bases derivatives synthesized by reactions of the amino heterocycles and aromatic aldehydes in our group (Wang et al., 2011), we present here the crystal structure of the title compound, (I).

The bond lengths and angles in (I) (Fig. 1) are normal and comparable with those reported for the related 1,2,4-triazole- 5(4H)-thione derivatives (Al-Tamimi et al., 2010; Fun et al. (2009); Tan et al. (2010); Wang et al., 2011;). The C1 and C2 atoms in the 1,2,4-triazole ring show distorted C_sp² hybridization states with the bond angles of 102.22 (9)° (N1—C1—N3), 129.64 (9)° (N3—C1—S1), 110.56 (10)° (N2—C2—N3) and 126.08 (11) ° (N2—C2—C25), which are in a good agreement with the literature (Zhao et al., 2010; Gao et al., 2011). The 1,2,4-triazole ring makes the dihedral angles of 102.4 (2), 61.4 (2) and 21.4 (2)° with phenyl rings (C6—C11 and C12—C17) and nitrophenyl ring (C19—C24), respectively.

In the crystal structure, weak intermolecular C—H···O hydrogen bonds (Table 1) and π—π interactions between the benzene rings from the neighbouring molecules with the centroid-centroid distance of 3.571 (3) Å consolidate the crystal packing.

Experimental

The title compound was synthesized by the reaction of 3-nitrobenzaldehyde (2.0 mmol) and 3-(4-amino-3-methyl-5-thioxo-4,5- dihydro-1H-1,2,4-triazol-1-yl)-1,3-diphenylpropan-1-one(2.0 mmol) by refluxing in ethnol. The reaction progress was monitored via TLC. The resulting precipitate was filtered off, washed with cold ethanol, dried and purified to give the target product as colourless solid in 75% yield. Crystals of (I) suitable for single-crystal X-ray analysis were grown by slow evaporation of a solution in chloroform-ethanol (1:1).