2-[(Anilino)(2-nitro­phen­yl)meth­yl]cyclo­hexa­none

Bagher Eftekhari-Sis; Sahar Mohajer; Orhan Büyükgüngör

doi:10.1107/S1600536812036859

. 2012 Sep 1;68(Pt 10):o2829. doi: 10.1107/S1600536812036859

2-[(Anilino)(2-nitrophenyl)methyl]cyclohexanone

Bagher Eftekhari-Sis ^a,^*, Sahar Mohajer ^a, Orhan Büyükgüngör ^b

PMCID: PMC3470191 PMID: 23125635

Abstract

In the title compound, C₁₉H₂₀N₂O₃, the cyclohexanone ring adopts a chair conformation with the aminomethyl group is positioned equatorially. An intramolecular N—H⋯O hydrogen bond occurs. In the crystal, molecules are linked by N—H⋯O hydrogen bonds.

Related literature

For the synthesis of the title compound and related compounds, see: Eftekhari-Sis et al. (2012a ▶,b ▶). For the biological activity of β-amino ketones, see: Arend et al. (1998 ▶). For the anti-inflammatory and antimicrobial activity of β-amino ketones, see: Jadhav et al. (2008 ▶) and Kalluraya et al. (2001 ▶), respectively. For information on the Mannich reaction, see: Eftekhari-Sis et al. (2006 ▶); Samet et al. (2009 ▶); Azizi et al. (2006 ▶); Cordova (2004 ▶). For related structures, see: Eftekhari-Sis et al. (2012b ▶); Yuan et al. (2007 ▶); Fun et al. (2009 ▶).

Experimental

Crystal data

C₁₉H₂₀N₂O₃
M _r = 324.37
Monoclinic,
a = 9.0535 (8) Å
b = 11.9947 (7) Å
c = 17.2267 (15) Å
β = 117.355 (6)°
V = 1661.5 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.62 × 0.43 × 0.21 mm

Data collection

Stoe IPDS 2 diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T _min = 0.784, T _max = 0.958
10888 measured reflections
3434 independent reflections
2210 reflections with I > 2σ(I)
R _int = 0.043

Refinement

R[F ² > 2σ(F ²)] = 0.054
wR(F ²) = 0.160
S = 0.97
3434 reflections
221 parameters
16 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.79 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2–8); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812036859/fj2593sup1.cif

e-68-o2829-sup1.cif^{(25.4KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812036859/fj2593Isup2.hkl

e-68-o2829-Isup2.hkl^{(165KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812036859/fj2593Isup3.mol

Supplementary material file. DOI: 10.1107/S1600536812036859/fj2593Isup4.cml

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

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1	0.85 (2)	2.31 (2)	2.906 (3)	127.0 (18)
N1—H1A⋯O2ⁱ	0.85 (2)	2.48 (2)	3.246 (3)	150.2 (19)

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Symmetry code: (i) Inline graphic .

Acknowledgments

The research council of the University of Maragheh is acknowledged for financial support.

supplementary crystallographic information

Comment

β-amino ketones are widely found in natural and un-natural products, which exhibit anti-inflammatory (Jadhav et al., 2008) and antimicrobial (Kalluraya et al., 2001) activities. Mannich reaction (Eftekhari-Sis et al., 2006; Samet et al., 2009; Azizi et al., 2006; Cordova, 2004) is one of the most important basic reactions in organic chemistry for its use in synthesis of β-Amino ketones. We have synthesized the title compound and report its structure here, Fig 1. The cyclohexanone ring adopts chair conformation, and aminomethyl moiety is positioned equatorially on ring at C1.

Experimental

The title compound was obtained by adding of 0.04 g of Laponite-HMPC nano composite (Eftekhari-Sis et al., 2012a,b) to a mixture of 0.5 mmol of 2-nitrobenzaldehyde, 0.5 mmol of aniline and 3 equiv. of cyclohexanone and stirring at room temperature for 24 h. After completion of the reaction, 5 ml EtOH was added and catalyst was removed by filtration, and filtrate was concentrated under reduced pressure. The obtained crud product was recrystallized from EtOH to afford title compound in 62% yield. Colorless crystals suitable for crystal structure determination were grown from EtOH.