1,2-Diphenyl-2-(m-tolyl­amino)ethanoneDedicated to the memory of Professor José Manuel Concellón.

Meroño, R.M.; Esculary, F.N.; Taboada, L.M.; García-Granda, S.

doi:10.1107/S1600536810013371

Volume 66
Part 5
Page o1107
May 2010

Received 19 March 2010
Accepted 11 April 2010
Online 17 April 2010

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R = 0.043
wR = 0.137
Data-to-parameter ratio = 13.3
Details

1,2-Diphenyl-2-(m-tolylamino)ethanone¹

Rafael Mendoza Meroño,^a Felix Nápoles Esculary,^b Laura Menéndez Taboada ^a and Santiago García-Granda ^a ^*

^aDepartamento de Química Física y Analítica, Facultad de Química, Universidad de Oviedo, C/ Julián Clavería, 8, 33006 Oviedo, Spain, and ^bDepartamento de Química, Facultad de Ciencias Naturales, Universidad de Oriente, Santiago de Cuba, Cuba
Correspondence e-mail: sgg@uniovi.es

The title compound, C₂₁H₁₉NO, belongs to the family of [alpha] -aminoketones. The structure contains three benzene rings, two of which [the phenyl ring in the 1-position (B) and the methylaniline ring (A)] are nearly coplanar [dihedral angle = 5.4 (1)°], whereas the phenyl ring in the 2-position (C) is nearly normal to them [dihedral angles = 81.8 (1) and 87.0 (1)° for A/C and B/C, respectively]. The conformation of the N-H bond is syn to the C=O bond, favouring the formation of a centrosymmetric dimer of molecules in the crystal structure. The molecular packing is consolidated by this N-HO hydrogen-bonding network.

Related literature

For the structure of alpha-aminoketones, see: Batsanov et al. (2006). For the crystal structure of 1,2-diphenyl-2-(p-tolylamino)ethanone, see: Au & Tafeenko (1986).

Experimental

Crystal data

C₂₁H₁₉NO
M_r = 301.37
Triclinic, $[P \overline 1]$
a = 6.0510 (3) Å
b = 11.5745 (4) Å
c = 12.9458 (7) Å
= 112.542 (5)°
= 97.396 (4)°
= 99.960 (4)°
V = 805.62 (8) Å³
Z = 2
Cu K radiation
= 0.59 mm^-1
T = 293 K
0.34 × 0.12 × 0.07 mm

Data collection

Oxford Diffraction Xcalibur Gemini S diffractometer
Absorption correction: refined from F [cubic fit to sin(theta)/lambda - 24 parameters; Parkin et al. (1995)] T_min = 0.919, T_max = 0.960
8027 measured reflections
2833 independent reflections
2174 reflections with I > 2(I)
R_int = 0.027

Refinement

R[F² > 2(F²)] = 0.043
wR(F²) = 0.137
S = 1.09
2833 reflections
213 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.25 e Å^-3
_min = -0.16 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H22O1ⁱ	0.859 (17)	2.660 (17)	3.3913 (17)	143.8 (15)
Symmetry code: (i) -x+1, -y+1, -z.

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); data reduction: CrysAlis RED; 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: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2170 ).

Acknowledgements

Financial support by the Agencia Española de Cooperación Internacional y Desarrollo (AECID), FEDER funding, the Spanish MICINN (MAT2006-01997 and Factoría de Cristalización Consolider Ingenio 2010) and the Gobierno del Principado de Asturias (PCTI) is acknowledged. Special acknowledgements go to Professor José Manuel Concellón for his support and scientific advice.

References

Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.
Au, O. & Tafeenko, V. (1986). Rev. Cubana Quim. 2, 65-74.
Batsanov, A. S., Goeta, A. E., Howard, J. A. K., Soto, B. & Au-Alvarez, O. (2006). Acta Cryst. C62, o304-o306.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.
Parkin, S., Moezzi, B. & Hope, H. (1995). J. Appl. Cryst. 28, 53-56.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds

1,2-Diphenyl-2-(m-tolylamino)ethanone1