1-Anilino-2-hexylsulfanyl-4,4-dimethyl-1<i>H</i>-imidazol-5(4<i>H</i>)-one

The racemic title compound, C(17)H(23)N(3)O(3), isolated from the reaction of L-(-)-tyrosine hydrazide with triethyl orthopropionate in the presence of a catalytic quantity of p-toluenesulfonic acid (p-TsOH), crystallizes with Z' = 1 in a centrosymmetric monoclinic unit cell. The molecule contains two planar fragments, viz. the benzene and imidazole rings, linked by two C-C single bonds. The dihedral angle between the two planes is 59.54 (5)° and the molecule adopts a synclinal conformation. The HOMA (harmonic oscillator model of aromaticity) index, calculated for the benzene ring, demonstrates no substantial interaction between the two π-electron delocalization regions in the molecule. In the crystal structure, there is an O-H...N hydrogen bond that links the molecules along the c axis.

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1-[(1-Ethoxypropylidene)amino]-2-ethyl-4-(4-hydroxybenzyl)imidazol-5(4H)-one

Ejsmont

Kudelko

Zieliński

2012

Acta Crystallogr C

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1-Anilino-2-hexylsulfanyl-4,4-dimethyl-1H-imidazol-5(4H)-one

Abstract: Key indicators: single-crystal X-ray study; T = 292 K; mean (C-C) = 0.003 Å; disorder in main residue; R factor = 0.053; wR factor = 0.157; data-to-parameter ratio = 18.2.

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1-[(1-Ethoxypropylidene)amino]-2-ethyl-4-(4-hydroxybenzyl)imidazol-5(4H)-one

1-[(1-Ethoxypropylidene)amino]-2-ethyl-4-(4-hydroxybenzyl)imidazol-5(4H)-one

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