1-[(Z)-2-Phenyl­hydrazin-1-yl­idene]-1-(piperidin-1-yl)propan-2-one

Hatem A Abdel-Aziz; Seik Weng Ng; Edward R T Tiekink

doi:10.1107/S1600536811029680

. 2011 Jul 30;67(Pt 8):o2172. doi: 10.1107/S1600536811029680

1-[(Z)-2-Phenylhydrazin-1-ylidene]-1-(piperidin-1-yl)propan-2-one

Hatem A Abdel-Aziz ^a,^‡, Seik Weng Ng ^c,^b, Edward R T Tiekink ^b,^*

PMCID: PMC3213607 PMID: 22091184

Abstract

A Z configuration about the imine bond [1.3025 (18) Å] in the title compound, C₁₄H₁₉N₃O, allows for the formation of an intramoleclar N—H⋯N hydrogen bond between the hydrazone H and piperidine N atoms; the carbonyl group is disposed to lie over the piperidine residue, which is in a chair form. A twist between the terminal benzene ring and the hydrazine residue is seen [N—N—C—C torsion angle = 163.81 (12)°]. Helical supramolecular chains along the c axis mediated by N—H⋯O hydrogen bonds are the most prominent feature of the crystal packing. The chains are connected into layers lying in the ac plane by weak C—H⋯π contacts involving two methylene H atoms and an adjacent benzene ring.

Related literature

For background to the biological activity of amidrazones, see: Frohberg et al. (2006 ▶); Abdel-Aziz & Mekawey (2009 ▶); Abdel-Aziz et al. (2010 ▶). For the synthesis, see: Frohberg et al. (1995 ▶).

Experimental

Crystal data

C₁₄H₁₉N₃O
M _r = 245.32
Orthorhombic,
a = 9.1195 (2) Å
b = 11.9614 (2) Å
c = 12.0393 (2) Å
V = 1313.27 (4) Å³
Z = 4
Cu Kα radiation
μ = 0.64 mm⁻¹
T = 100 K
0.25 × 0.10 × 0.05 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T _min = 0.857, T _max = 0.969
5335 measured reflections
2589 independent reflections
2482 reflections with I > 2σ(I)
R _int = 0.021

Refinement

R[F ² > 2σ(F ²)] = 0.033
wR(F ²) = 0.080
S = 1.05
2589 reflections
168 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.12 e Å⁻³
Δρ_min = −0.20 e Å⁻³
Absolute structure: Flack (1983 ▶), 1077 Friedel pairs
Flack parameter: −0.1 (3)

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811029680/hb6327sup1.cif

e-67-o2172-sup1.cif^{(18.1KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811029680/hb6327Isup2.hkl

e-67-o2172-Isup2.hkl^{(127.2KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811029680/hb6327Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

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

Cg1 is the centroid of the C9–C14 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯O1ⁱ	0.88 (2)	2.47 (2)	3.2317 (15)	145.6 (17)
N3—H3⋯N1	0.88 (2)	2.242 (19)	2.6340 (16)	106.8 (15)
C2—H2b⋯Cg1ⁱⁱ	0.99	2.77	3.5535 (16)	137
C3—H3a⋯Cg1ⁱⁱⁱ	0.99	2.98	3.9473 (16)	167

Open in a new tab

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

Acknowledgments

The authors thank King Saud University and the University of Malaya for supporting this study.

supplementary crystallographic information

Comment

The title compound (I) and related amidrazone derivatives are known to possess biological activity (Frohberg et al., 2006), the motivation for on-going studies in this area (Abdel-Aziz & Mekawey, 2009; Abdel-Aziz et al., 2010). In the molecule of (I), Fig. 1, the configuration about the imine N2═C6 bond [1.3025 (18) Å] is Z. This places the hydrazone-N3—H in close proximity to the piperidinyl-N1 enabling the formation of an intramolecular N—H···N hydrogen bond (Table 1). The carbonyl group is disposed to lie over the piperidinyl group which adopts a chair conformation. The benzene group is twisted out of the plane through the hydrazine residue to which it is connected as seen in the value of the N2—N3—C9—C10 torsion angle of 163.81 (12) °. The piperidinyl group is disposed to be almost normal to the rest of the molecule so that the dihedral plane formed through its least-squares plane and that through the O1,N2,N3,C6,C7,C9 atoms is 85.26 (6) °.

In the crystal, molecules are connected into a helical supramolecular chain mediated by N—H···O hydrogen bonds (Table 1). Chains are orientated along the c axis and are connected into a supramolecular array in the ac plane by C—H···π interactions involving methylene-H atoms associated with the bifurcated benzene ring (Table 1 and Fig. 2).

Experimental

This compound was prepared by the reaction of 2-oxo-N'-phenylpropanehydrazonoyl chloride with piperidine (Frohberg et al., 1995). The yellow prisms of (I) were isolated from its ethanol solution by slow evaporation at room temperature.