N′-(Adamantan-2-yl­idene)benzo­hydrazide

Maha S Almutairi; Ali A El-Emam; Nasser R El-Brollosy; Mohammed Said-Abdelbaky; Santiago García-Granda

doi:10.1107/S1600536812028644

. 2012 Jun 30;68(Pt 7):o2247–o2248. doi: 10.1107/S1600536812028644

N′-(Adamantan-2-ylidene)benzohydrazide

Maha S Almutairi ^a, Ali A El-Emam ^a,^‡, Nasser R El-Brollosy ^a, Mohammed Said-Abdelbaky ^b, Santiago García-Granda ^b,^*

PMCID: PMC3394036 PMID: 22798901

Abstract

The title molecule, C₁₇H₂₀N₂O, is a functionalized hydrazine with benzoyl and adamantyl substituents attached to the two hydrazine N atoms. In the crystal, molecules are linked via N—H⋯N hydrogen bonds, forming chains propagating along the a-axis direction. There are also C—H⋯O, C—H⋯N and C—H⋯π interactions present within the chains.

Related literature

For the biological activity of adamantane derivatives, see: Togo et al. (1968 ▶); Kadi et al. (2007 ▶, 2010 ▶); Al-Deeb et al. (2006 ▶); El-Emam et al. (2004 ▶). For the biological activity of hydrazone derivatives, see: Zheng et al. (2009 ▶); Moldovan et al. (2011 ▶). For related adamantane structures, see: Almutairi et al. (2012 ▶); Rouchal et al. (2010 ▶); El-Emam et al. (2012 ▶). For related cyclic ketone hydrazone structures, see: Sankar et al. (2010 ▶); El-Emam & Ibrahim (1991 ▶); Kia et al. (2009 ▶); Kadi et al. (2011 ▶).

Experimental

Crystal data

C₁₇H₂₀N₂O
M _r = 268.35
Orthorhombic,
a = 7.9698 (3) Å
b = 17.5466 (8) Å
c = 20.1350 (8) Å
V = 2815.7 (2) Å³
Z = 8
Cu Kα radiation
μ = 0.62 mm⁻¹
T = 120 K
0.26 × 0.08 × 0.02 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010 ▶) T _min = 0.942, T _max = 0.988
7280 measured reflections
2634 independent reflections
1859 reflections with I > 2σ(I)
R _int = 0.052

Refinement

R[F ² > 2σ(F ²)] = 0.051
wR(F ²) = 0.139
S = 1.03
2634 reflections
185 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Data collection: CrysAlis CCD (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2010 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812028644/su2467sup1.cif

e-68-o2247-sup1.cif^{(20.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812028644/su2467Isup2.hkl

e-68-o2247-Isup2.hkl^{(126.8KB, hkl)}

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

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

Cg1 is the centroid of the C2–C7 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯N2ⁱ	0.95 (2)	2.17 (2)	3.087 (2)	162 (2)
C3—H3⋯O1ⁱ	0.93	2.47	3.381 (3)	167
C9—H9⋯O1ⁱ	0.98	2.33	3.210 (3)	149
C9—H9⋯N2ⁱ	0.98	2.55	3.402 (3)	145
C15—H15A⋯Cg1ⁱⁱ	0.97	2.57	3.519 (3)	164

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

Acknowledgments

The financial support of the Deanship of Scientific Research and the Research Center for Female Scientific and Medical Colleges, King Saud University, is greatly appreciated. Financial support from the Spanish Ministerio de Economía y Competitividad (MAT2010–15094, MAT2006–01997, Factoría de Cristalización – Consolider Ingenio 2010, and FPI grant BES-2011–046948 to MSM-A) and FEDER are gratefully acknowledged.

supplementary crystallographic information

Comment

Derivatives of adamantane have long been known for their diverse biological activities including antiviral activity against the influenza (Togo et al., 1968) and HIV viruses (El-Emam et al., 2004). Moreover, adamantane derivatives were reported to exhibit marked antibacterial and anti-inflammatory activities (Kadi et al., 2007, 2010; El-Emam & Ibrahim, 1991). In continuation to our interest in the chemical and pharmacological properties of adamantane derivatives (Almutairi et al., 2012; El-Emam et al., 2012), we synthesized the title compound as a precursor for potential chemotherapeutic agents. Herein, we report on the synthesis and crystal structure of the title compound.

The title molecule, Fig. 1, is a functionalized hydrazine with benzoyl and adamantyl substituents attached to the two hydrazine nitrogen atoms, N1 and N2.

In the crystal, molecules are linked via N-H···N hydrogen bonds forming chains propagating along the a axis direction. There are also C-H···O, C-H···N and C-H···π interactions present within the chains (Table 1).

Experimental

A mixture of benzohydrazide (1.36 g, 0.01 mol), 2-adamantanone (1.5 g, 0.01 mol), in ethanol (10 ml) was heated under reflux with stirring for 4 h. On cooling, the precipitated crystalline solid was filtered, dried and recrystallized from ethanol to yield 2.52 g (94%) of the title compound as colourless needle crystals [M.p. 517-519 K]. Spectroscopic data for the title compound are given in the archived CIF.