Abstract
Two independent mol-ecules (A and B) comprise the asymmetric unit of the title compound, C18H21N3O3. The urea moiety is disubstituted with one amine being linked to a phenyl ring, which is twisted out of the plane of the CN2O urea core [dihedral angles = 25.57 (11) (A) and 29.13 (10)° (B)]. The second amine is connected to an imine (E conformation), which is linked in turn to an ethane bridge that links a disubstituted benzene ring. Intra-molecular amine-N-H⋯N(imine) and hydroxyl-O-H⋯O(meth-oxy) hydrogen bonds close S(5) loops in each case. The mol-ecules have twisted conformations with the dihedral angles between the outer rings being 38.64 (81) (A) and 48.55 (7)° (B). In the crystal, amide-N-H⋯O(amide) hydrogen bonds link the mol-ecules A and B via an eight-membered {⋯HNCO}2 synthon. Further associations between mol-ecules, leading to supra-molecular layers in the ac plane, are hydrogen bonds of the type hydroxyl-O-H⋯N(imine) and phenyl-amine-N-H⋯O(meth-oxy). Connections between layers, leading to a three-dimensional architecture, comprise benzene-C-H⋯O(hy-droxy) inter-actions. A detailed analysis of the calculated Hirshfeld surfaces shows mol-ecules A and B participate in very similar inter-molecular inter-actions and that any variations relate to conformational differences between the mol-ecules.
Highlights
O6—H6OÁ Á ÁO5 O3—H3OÁ Á ÁN6i O6—H6OÁ Á ÁN3ii N2—H2NÁ Á ÁO4iii N4—H4NÁ Á ÁO2i N5—H5NÁ Á ÁO1iv C33—H33Á Á ÁO6v C15—H15Á Á ÁO3vi C33—H33Á Á ÁO6i C10—H10AÁ Á ÁCg1vii C18—H18AÁ Á ÁCg2ii C28—H28BÁ Á ÁCg3viii
Each molecule features a disubstituted urea molecule with one amine group connected to a phenyl ring and the other linked to a disubstituted imine group, with the longer side-chain carrying an ethane chain terminating with a disubstituted benzene ring
The hydroxyl-O3—HÁ Á ÁN6(imine) interaction is incorporated within a 10-membered {Á Á ÁHOC2OÁ Á ÁHNCNN} heterosynthon owing to the formation of a relatively weak phenylamineN4—HÁ Á ÁO2(methoxy) hydrogen bond
Summary
Semicarbazones belong to the general class of molecules termed Schiff bases and are prepared from condensation of semicarbazides with aldehydes/ketones They have attracted considerable attention due to their wide spectrum of biological activities, including anti-convulsant (Pandey & Srivastava, 2010), anti-tubercular (Sriram et al, 2004), anti-cancer (Ali et al, 2012) and anti-microbial (Beraldo & Gambino, 2004). The crystal structures of related chalcone-derived thiosemicarbazones and their transition metal complexes have been reported (Tan et al, 2015, 2017). In this contribution, aryl semicarbazide is introduced with vanillylacetone, which led to the formation of the title compound. Àx þ 32; y þ 12; Àz þ 12; (iv) Àx þ 32; y À 12; Àz þ 12; (v) Àx þ 1; Ày À 1; Àz þ 1; (vi) Àx; Ày þ 2; Àz; (vii) x; y þ 1; z; (viii) x; y À 1; z
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