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

Wei Wang; Wei-Min Jia; Chao Xu; Wen-Peng Wu; Qing-Lei Liu

doi:10.1107/S1600536811043777

. 2011 Oct 29;67(Pt 11):o3135. doi: 10.1107/S1600536811043777

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

Wei Wang ^a,^b,^*, Wei-Min Jia ^a, Chao Xu ^b, Wen-Peng Wu ^b, Qing-Lei Liu ^a

PMCID: PMC3247519 PMID: 22220137

Abstract

In the title compound, C₂₅H₂₁N₅O₃S·CH₂Cl₂, the dichloromethane solvent molecule is disordered over four positions, with an occupancy ratio of 0.271 (3):0.3884 (18):0.298 (2):0.0424 (15). The 1,2,4-triazole ring makes dihedral angles of 47.3 (2)/87.3 (2) and 3.6 (2)° with the phenyl and nitrophenyl rings, respectively. An intramolecular C—H⋯S hydrogen bond results in the formation of an almost planar six-membered ring [r.m.s. derivation = 0.0051 (2) Å]. Intermolecular C—H⋯O hydrogen bonding consolidates the structure.

Related literature

For crystal structures related to 1,2,4-triazole-5(4H)-thione, 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·CH₂Cl₂
M _r = 556.45
Triclinic,
a = 8.9880 (13) Å
b = 11.4440 (15) Å
c = 14.8604 (18) Å
α = 70.212 (11)°
β = 88.973 (13)°
γ = 67.020 (9)°
V = 1312.6 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.37 mm⁻¹
T = 113 K
0.26 × 0.24 × 0.20 mm

Data collection

Rigaku Saturn CCD diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T _min = 0.911, T _max = 0.931
16932 measured reflections
6203 independent reflections
4100 reflections with I > 2σ(I)
R _int = 0.035

Refinement

R[F ² > 2σ(F ²)] = 0.052
wR(F ²) = 0.159
S = 1.07
6203 reflections
396 parameters
91 restraints
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.41 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: CrystalStructure (Rigaku/MSC, 2007 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811043777/zk2024sup1.cif

e-67-o3135-sup1.cif^{(27.1KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811043777/zk2024Isup2.hkl

e-67-o3135-Isup2.hkl^{(303.6KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811043777/zk2024Isup3.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
C19—H19⋯S1	0.95	2.43	3.199 (3)	137
C18—H18B⋯O1ⁱ	0.98	2.55	3.443 (4)	152
C22—H22⋯O1ⁱⁱ	0.95	2.34	3.202 (3)	151

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

Acknowledgments

The authors gratefully acknowledge support of this project by the Key Laboratory Project of Liaoning Province (grant No. 2008S127) and by the Doctor Starting Foundation of Liaoning Province (grant No. 20071103).

supplementary crystallographic information

Comment

In continuation of our structural studies of derivatives of Mannich bases synthesized from amino heterocycles and aromatic aldehydes in our group (Wang et al., 2011), we present here the crystal structure of the title compound named 3-[4-(4-Nitrobenzylideneamino)-5-thioxo-3-(4-tolyl)-4,5- dihydro-1H-1,2,4-triazol-1-yl]-1,3-diphenylpropan-1-one.

The bond lengths and angles in title compound are found to have normal values comparable with those reported in 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). An intramolecular C—H···S hydrogen bond results in the formation of a planar [an r.m.s. deviation of 0.0051 (2) Å] six-membered ring (Table 1) and the maxmium deviation of 0.0088 (2) Å for atom N4. The 1,2,4-triazole ring is almost planar with an r.m.s. deviation of 0.0039 (2) Å and the maxmium deviation of 0.0061 (2) Å for atom N1. The 1,2,4-triazole ring mean plane forms the dihedral angles of 47.3 (2), 87.3 (2) and 3.6 (2)° with two phenyl rings (C1–C6 and C10–C15) and nitrophenyl ring, respectively. Two C atoms in the 1,2,4-triazole ring show distorted Csp² hybridization states with the bond angles of 101.95 (16)° (N1—C16—N3), 130.44 (15)° (N3—C16—S1), 110.44 (18)° (N2—C17—N3) and 25.88 (19)° (N3—C17—C18), which are similar to those of similar reported triazole derivatives (Zhao et al., 2010; Gao et al., 2011).

In the crystal structure, weak intermolecular C—H···O hydrogen bonds (Table 1) are observed and consolidate the crystal structure.

Experimental

The title compound was synthesized with the reaction of 4-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 ethanol. 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 a colorless solid in 74% yield. Crystals of title compound suitable for single-crystal X-ray analysis were grown by slow evaporation of a solution in dichloromethanle–ethanol (1:1).