2-[2-(4-Acetyl­phen­yl)hydrazinyl­idene]-1,3-diphenyl­propane-1,3-dione

Bustos, C.; Barría, D.; Alvarez-Thon, L.; Cárcamo, J.-G.; Garland, M.T.

doi:10.1107/S1600536811027590

Volume 67
Part 8
Pages o2048-o2049
August 2011

Received 8 July 2011
Accepted 9 July 2011
Online 16 July 2011

Key indicators
Single-crystal X-ray study
T = 297 K
Mean (C-C) = 0.002 Å
R = 0.042
wR = 0.117
Data-to-parameter ratio = 15.0
Details

2-[2-(4-Acetylphenyl)hydrazinylidene]-1,3-diphenylpropane-1,3-dione

Carlos Bustos,^a Daniela Barría,^a Luis Alvarez-Thon,^b ^* Juan-Guillermo Cárcamo ^c and Maria Teresa Garland ^d

^aInstituto de Ciencias Químicas, Universidad Austral de Chile, Avda. Los Robles s/n, Campus Isla Teja, Casilla 567, Valdivia, Chile,^bDepartamento de Ciencias Físicas, Universidad Andres Bello, Avda. República 220, Santiago de Chile, Chile,^cInstituto de Ciencias Moleculares y Microbiología, Universidad Austral de Chile, Avda. Los Robles s/n, Campus Isla Teja, Casilla 567, Valdivia, Chile, and ^dLaboratorio de Cristalografía, Departamento de Física, Facultad de Ciencias Físicas y Matemáticas, Universidad de Chile, Av. Blanco Encalada 2008, Santiago de Chile, Chile
Correspondence e-mail: lalvarez@unab.cl

In the title compound, C₂₃H₁₈N₂O₃, the interplanar angle between the benzoyl units is 80.51 (6)° while the dihedral angles between the hydrazinylidene and benzoyl groups are 43.43 (6) and 54.16 (6)°. In the crystal, a strong resonance-assisted intramolecular N-HO hydrogen bond is observed. The molecules form an inversion dimer via a pair of weak C-HO hydrogen bonds and a [pi] - [pi] interaction [centroid-centroid distance of 3.5719 (10) Å]. These dimers are linked via weak C-HO contacts, forming chains along the b axis.

Related literature

For details of the synthesis, see: Yao (1964). For resonance-assisted hydrogen bonds and related structures see: Bertolasi et al. (1993); Bustos, Alvarez-Thon, Barría, Cárcamo & Garland (2011); Bustos, Alvarez-Thon, Barría, Garland & Sánchez (2011); Bustos, Alvarez-Thon, Cárcamo, Garland & Sánchez (2011); Bustos, Alvarez-Thon, Cárcamo, Ibañez & Sánchez (2011); Gilli et al. (1993).

Experimental

Crystal data

C₂₃H₁₈N₂O₃
M_r = 370.39
Monoclinic, P 2₁ /n
a = 12.6026 (15) Å
b = 11.0138 (13) Å
c = 14.9701 (18) Å
= 114.447 (2)°
V = 1891.6 (4) Å³
Z = 4
Mo K radiation
= 0.09 mm^-1
T = 297 K
0.53 × 0.23 × 0.20 mm

Data collection

Bruker D8 Discover with SMART CCD area-detector diffractometer
14867 measured reflections
3869 independent reflections
2580 reflections with I > 2(I)
R_int = 0.047

Refinement

R[F² > 2(F²)] = 0.042
wR(F²) = 0.117
S = 0.97
3869 reflections
258 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.23 e Å^-3
_min = -0.14 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H1O2	0.888 (15)	1.965 (15)	2.6496 (16)	132.8 (15)
C15-H15O3ⁱ	0.93	2.38	3.2503 (19)	156
C21-H21O1ⁱⁱ	0.93	2.67	3.2983 (18)	125
Symmetry codes: (i) -x+2, -y+1, -z; (ii) -x+2, -y, -z.

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL-PC (Sheldrick, 2008); software used to prepare material for publication: PLATON (Spek, 2009) and Mercury (Macrae et al., 2008).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FJ2443 ).

Acknowledgements

The authors thank the Fondo Nacional de Desarrollo Científico y Tecnológico (FONDECYT; grant Nos. 11100446 and 1080269) and the Universidad Andrés Bello (grant No. DI-06-10-R) for financial assistance.

References

Bertolasi, V., Ferretti, V., Gilli, P., Gilli, G., Issa, Y. M. & Sherif, O. E. (1993). J. Chem. Soc. Perkin Trans. 2, pp. 2223-2228.
Bruker (2000). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2001). SMART. Bruker AXS Inc., Madison, Wisconsin, USA.
Bustos, C., Alvarez-Thon, L., Barría, D., Cárcamo, J.-G. & Garland, M. T. (2011). Acta Cryst. E67, o1830-o1831.
Bustos, C., Alvarez-Thon, L., Barría, D., Garland, M. T. & Sánchez, C. (2011). Acta Cryst. E67, o1587.
Bustos, C., Alvarez-Thon, L., Cárcamo, J.-G., Garland, M. T. & Sánchez, C. (2011). Acta Cryst. E67, o1426.
Bustos, C., Alvarez-Thon, L., Cárcamo, J.-G., Ibañez, A. & Sánchez, C. (2011). Acta Cryst. E67, o1450-o1451.
Gilli, G., Bertolasi, V., Ferretti, V. & Gilli, P. (1993). Acta Cryst. B49, 564-576.
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Yao, H. C. (1964). J. Org. Chem. 29, 2959-2962.

organic compounds