Crystal structure of (E)-3-[4-(benzyl­idene­amino)-5-sulfanyl­idene-3-(p-tol­yl)-4,5-di­hydro-1H-1,2,4-triazol-1-yl]-3-(4-meth­oxy­phen­yl)-1-phenyl­propan-1-one

Hewen Wang

doi:10.1107/S2056989015023804

. 2015 Dec 24;71(Pt 12):o1080–o1081. doi: 10.1107/S2056989015023804

Crystal structure of (E)-3-[4-(benzylideneamino)-5-sulfanylidene-3-(p-tolyl)-4,5-dihydro-1H-1,2,4-triazol-1-yl]-3-(4-methoxyphenyl)-1-phenylpropan-1-one

Hewen Wang ^a,^*

PMCID: PMC4719989 PMID: 26870508

Abstract

The title compound, C₃₂H₂₈N₄O₂S, crystallizes as a racemate. In the molecule, the bond-angle sum at the C atom of the sulfanylidene entity bound to the triazole ring is 360°, with an annular N—C—N bond angle of 102.6 (2)° and two larger N—C—S angles of 127.3 (2) and 130.1 (2)°. The essentially planar 1,2,4-triazole ring (r.m.s. deviation = 0.013 Å) is nearly perpendicular to the phenylpropanone and methoxyphenyl rings , making dihedral angles of 76.9 (2) and 85.2 (2)°, respectively and subtends dihedral angles of 17.6 (2) and 40.3 (2)° with the tolyl and benzylideneamino rings, respectively. There is no π–π stacking between the molecules. The crystal packing is dominated by weak C—H⋯O and C—H⋯N interactions, leading to a three-dimensional network structure. An intramolecular C—H⋯S interaction also occurs.

Keywords: crystal structure; 1,2,4-triazole derivative; Mannich reaction

Related literature

Mannich base derivatives are used in numerous applications, e.g. in agrochemistry, pharmacy and polymer chemistry. Synthesis and crystal structures of such compounds were reported recently (Wang et al., 2011 ▸; Shams et al., 2011 ▸). Bond lengths and angles of the title compound are comparable with related 1,2,4-triazole-5(4H)-thione derivatives (Al-Tamimi et al., 2010 ▸; Fun et al., 2009 ▸; Tan et al., 2010 ▸). For the crystal structures of other triazole derivatives, see: Zhao et al. (2010 ▸); Gao et al. (2011 ▸). graphic file with name e-71-o1080-scheme1.jpg

Experimental

Crystal data

C₃₂H₂₈N₄O₂S
M _r = 532.64
Triclinic,
a = 6.2343 (6) Å
b = 14.6968 (14) Å
c = 15.0540 (17) Å
α = 90.234 (9)°
β = 92.612 (13)°
γ = 99.497 (10)°
V = 1358.9 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.16 mm⁻¹
T = 113 K
0.20 × 0.18 × 0.12 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▸) T _min = 0.969, T _max = 0.982
11718 measured reflections
4778 independent reflections
3450 reflections with I > 2σ(I)
R _int = 0.057

Refinement

R[F ² > 2σ(F ²)] = 0.065
wR(F ²) = 0.126
S = 1.08
4778 reflections
354 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.25 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, 2005 ▸).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015023804/wm5250sup1.cif

e-71-o1080-sup1.cif^{(25KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015023804/wm5250Isup2.hkl

e-71-o1080-Isup2.hkl^{(234KB, hkl)}

Click here for additional data file.^{(10.3KB, cml)}

Supporting information file. DOI: 10.1107/S2056989015023804/wm5250Isup3.cml

Click here for additional data file.^{(1.3MB, tif)}

. DOI: 10.1107/S2056989015023804/wm5250fig1.tif

View of the title molecule showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.

CCDC reference: 1441814

Additional supporting information: crystallographic information; 3D view; checkCIF report

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯N2	0.95	2.60	3.250 (4)	126
C20—H20⋯N4	0.95	2.39	2.990 (4)	121
C24—H24⋯O1ⁱ	0.95	2.58	3.464 (4)	156
C26—H26⋯S1	0.95	2.71	3.188 (3)	112

Open in a new tab

Symmetry code: (i) Inline graphic .

supplementary crystallographic information

S1. Experimental

The title compound was synthesized by the reaction of benzaldehyde (2.0 mmol) and 3-(4-amino-5-thioxo-3-(p-tolyl)-4,5-dihydro-1H-1,2,4-triazol-1-yl)-3-(4-methoxyphenyl)-1-phenylpropan-1-one (2.0 mmol) under reflux 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 75% yield. Crystals of the title compound suitable for single-crystal X-ray analysis were grown by slow evaporation of a chloroform-ethanol (1:1, v/v) mixture.