2-[Anilino(phen­yl)meth­yl]cyclo­heptan­one

Bagher Eftekhari-Sis; Sahar Mohajer; Maryam Zirak; Sakineh Mozaffarnia; Orhan Büyükgüngör

doi:10.1107/S1600536812050659

. 2012 Dec 19;69(Pt 1):o109. doi: 10.1107/S1600536812050659

2-[Anilino(phenyl)methyl]cycloheptanone

Bagher Eftekhari-Sis ^a,^*, Sahar Mohajer ^a, Maryam Zirak ^b, Sakineh Mozaffarnia ^a, Orhan Büyükgüngör ^c

PMCID: PMC3588277 PMID: 23476371

Abstract

In the title compound, C₂₀H₂₃NO, the cycloheptanone ring adopts a twist-chair conformation, with the aminomethyl substituent in an equatorial position. The relative configuration of the two stereocenters is R,R. In the crystal, molecules are linked by N—H⋯O hydrogen bonds into chains along [100].

Related literature

For the synthesis of title compound and related compounds, see: Eftekhari-Sis et al. (2013 ▶). For the biological activity of β-amino ketones, see: Arend et al. (1998 ▶); Jadhav et al. (2008 ▶); Kalluraya et al. (2001 ▶). For information on the Mannich reaction, see, for example: Eftekhari-Sis et al. (2006 ▶); Azizi et al. (2006 ▶); Cordova (2004 ▶). For the crystal structures of related compounds, see: Eftekhari-Sis et al. (2012 ▶); Yuan et al. (2007 ▶); Fun et al. (2009 ▶). For puckering parameters, see: Evans & Boeyens (1989 ▶). graphic file with name e-69-0o109-scheme1.jpg

Experimental

Crystal data

C₂₀H₂₃NO
M _r = 293.39
Monoclinic,
a = 5.7534 (4) Å
b = 16.1336 (8) Å
c = 18.1980 (13) Å
β = 99.371 (6)°
V = 1666.65 (19) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 296 K
0.72 × 0.56 × 0.27 mm

Data collection

Stoe IPDS 2 diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T _min = 0.965, T _max = 0.985
10757 measured reflections
3449 independent reflections
2170 reflections with I > 2σ(I)
R _int = 0.041

Refinement

R[F ² > 2σ(F ²)] = 0.048
wR(F ²) = 0.136
S = 1.01
3449 reflections
203 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.13 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, 2008) ▶; molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Supplementary Material

Click here for additional data file.^{(19.5KB, cif)}

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812050659/fy2069sup1.cif

e-69-0o109-sup1.cif^{(19.5KB, cif)}

Click here for additional data file.^{(165.8KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812050659/fy2069Isup2.hkl

e-69-0o109-Isup2.hkl^{(165.8KB, hkl)}

Click here for additional data file.^{(4.5KB, mol)}

Supplementary material file. DOI: 10.1107/S1600536812050659/fy2069Isup3.mol

Click here for additional data file.^{(6.3KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536812050659/fy2069Isup4.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⋯O1ⁱ	0.879 (19)	2.23 (2)	3.065 (2)	158.4 (16)

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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

Mannich reaction (Eftekhari-Sis et al., 2006; Azizi et al., 2006; Cordova, 2004) is one of the most important basic reactions in organic chemistry for its use in natural product and pharmaceutical syntheses due to formation of C—C and C—N bonds, simultaneously, to furnish β-amino ketones, which exhibit biological activity such as anti-inflammatory (Jadhav et al., 2008) and antimicrobial (Kalluraya et al., 2001) activities. We have synthesized the title compound and report its structure here, Fig 1. The cycloheptanone ring adopts twist-chair conformation, with puckering parameters of Q(2) = 0.539 (2) Å, Φ(2) = 41.7 (2)° and Q(3) = 0.644 (2) Å, Φ(3) = 319.2 (2)° (Evans & Boeyens, 1989). The aminomethyl moiety is positioned equatorially on the ring at C1.

Experimental

The title compound was obtained by adding of 0.04 g of Laponite-HPMC nano composite (Eftekhari-Sis et al., 2013) to a mixture of 0.5 mmol of benzaldehyde, 0.5 mmol of aniline and 3 equiv. of cycloheptanone and stirring at room temperature for 24 h. After completion of the reaction, 5 ml EtOH was added and the catalyst was removed by filtration. The filtrate was concentrated under reduced pressure. The obtained crude product was recrystallized from EtOH to afford the title compound in 60% yield. Colorless crystals suitable for crystal structure determination were grown from 96% EtOH.