(E)-N-(4-{[1-(Prop-2-en-1-yl)-1H-1,2,3-triazol-4-yl]methoxy}benzylidene)morpholin-4-amine

The asymmetric unit of the title compound, C17H21N5O2, contains two crystallographically independent molecules, which are linked by a C—H⋯N hydrogen bond. The morpholine rings of both molecules adopt distorted chair conformations. The dihedral angles between the triazole and benzene rings are 12.8 (3)° in the first independent molecule in which the –N=C– group between the morpholine and benzene rings is disordered [site-occupancy ratio = 0.576 (7):0.424 (7)] and 88.1 (2)° in the second independent molecule. In the crystal, molecules are linked by C—H⋯N hydrogen bonds along the [100] direction. In addition, one weak C—H⋯π interaction and two weak π–π stacking interactions [centroid–centroid distances = 3.840 (3) and 3.823 (2) Å] between the triazole rings of adjacent molecules are observed. The atoms of the terminal propenyl groups in both molecules are disordered over two sets of sites [site-occupancy ratios = 0.691 (10):0.309 (10) and 0.705 (15):0.295 (15)].

The asymmetric unit of the title compound, C 17 H 21 N 5 O 2 , contains two crystallographically independent molecules, which are linked by a C-HÁ Á ÁN hydrogen bond. The morpholine rings of both molecules adopt distorted chair conformations. The dihedral angles between the triazole and benzene rings are 12.8 (3) in the first independent molecule in which the -N C-group between the morpholine and benzene rings is disordered [site-occupancy ratio = 0.576 (7):0.424 (7)] and 88.1 (2) in the second independent molecule. In the crystal, molecules are linked by C-HÁ Á ÁN hydrogen bonds along the [100] direction. In addition, one weak C-HÁ Á Á interaction and two weakstacking interactions [centroid-centroid distances = 3.840 (3) and 3.823 (2) Å ] between the triazole rings of adjacent molecules are observed. The atoms of the terminal propenyl groups in both molecules are disordered over two sets of sites [siteoccupancy ratios = 0.691 (10):0.309 (10) and 0.705 (15): 0.295 (15)].

Comment
Schiff bases are present in various natural, semi-synthetic, and synthetic compounds and have been demonstrated to be essential for their biological activities (Bringmann et al., 2004). Triazoles constitute an important class of heterocycles because of their varied biological activities (Singh et al., 2012). 1,2,3-Triazoles are attractive constructs, because of their unique chemical properties and they find many applications in organic and medicinal chemistry (Nithinchandra et al., 2013). They are found to be potent antimicrobial and antiviral agents (Sherement et al., 2004). The morpholine moiety has been utilized extensively by the pharmaceutical industry in drug design, often because of the improvement in pharmacokinetic properties it can confer. The biological utility of molecules containing the morpholine moiety is wideranging (Nelson et al., 2004). Therefore, compound (I), which has the triazole and the morpholine moieties in one molecule, has beeb synthesized and its X-ray studies is reported here. Fig. 1 shows two crystallographically independent molecules in the asymmetric unit of the title compound. The morpholine rings of both molecules adopts distorted chair conformations [puckering parameters (Cremer & Pople, 1975) are Q T = 0.415 (6) Å, θ = 4.2 (7)°, φ = 5(10)° and Q T = 0.519 (6) Å, θ = 173.1 (7)°, φ = 169 (6)°, respectively]. The dihedral angles between the triazole and benzene rings of both molecules are 12.8 (3) and 88.1 (2) °, respectively. All bond lengths and bond angles in (I) are normal and comparable to those given for the similar compounds (Akkurt et al., 2013a,b).

Refinement
H atoms were located geometrically and were refined using a riding model with U iso (H) = 1.2U eq (C). The atoms of the terminal propenyl groups of the two molecules in the asymmetric unit are disordered over two sets of sites, with the siteoccupancy ratios of 0.691 (10): 0.309 (10) and 0.705 (15): 0.295 (15), respectively. The -N2═C5-group between the morpholine and benzene rings of the one molecule is also disordered over two positions [site-occupancy ratio = 0.576 (7): 0.424 (7)]. The small proportion of reflections observed is a result of the rather poor quality of the very thin crystals obtained.

Figure 1
The title molecule (I) with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 30% probability level. Only major disorder component is shown.

(E)-N-(4-{[1-(Prop-2-en-1-yl)-1H-1,2,3-triazol-4-yl]methoxy}benzylidene)morpholin-4-amine
Special details Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles Refinement. Refinement on F 2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The observed criterion of F 2 > σ(F 2 ) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.