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Volume 68 
Part 11 
Page o3143  
November 2012  

Received 11 August 2012
Accepted 2 October 2012
Online 20 October 2012

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.002 Å
R = 0.044
wR = 0.121
Data-to-parameter ratio = 13.7
Details
Open access

[(E)-1-(Naphthalen-2-yl)ethylidene](naphthalen-1-ylmethyl)amine

aDepartment of Chemistry, University of Aveiro, CICECO, 3810-193, Aveiro, Portugal
Correspondence e-mail: filipe.paz@ua.pt

The title compound, C23H19N, was obtained unexpectedly from the reaction of [Eu(nta)3(PzPy)] {Hnta = 1-(2-naphthoyl)-3,3,3-trifluoroacetone and PzPy = 2-[3(5)-pyrazolyl]pyridine} with 1-naphthylmethylamine. The 1- and 2-naphthyl groups are essentially planar [r.m.s. deviations of 0.007 and 0.011 Å, respectively] and subtend angles of 38.69 (11) and 16.50 (11)°, respectively, with the central CH3-C=N-CH2 unit, which is also almost planar [r.m.s. deviation = 0.002 Å]. In the crystal, the molecules are disposed in zigzag-type fashion, forming layers perpendicular to [100]. Weak supramolecular C-H...[pi] interactions contribute to the packing forces.

Related literature

For general background to aldimidines and ketimines, see: Norton et al. (1954[Norton, D. G., Haury, V. E., Davis, F. C., Mitchell, L. J. & Ballard, S. A. (1954). J. Org. Chem. 19, 1054-1066.]); Hampe et al. (2004[Hampe, D., Günther, W., Görls, H. & Anders, E. (2004). Eur. J. Org. Chem. pp. 4357-4372.]) and references cited therein; Kumar et al. (2008[Kumar, A., Agarwal, M. & Singh, A. K. (2008). Polyhedron, 27, 485-492.]). For general background to [beta]-diketonates, see: Bruno et al. (2008[Bruno, S. M., Ferreira, R. A. S., Carlos, L. D., Pillinger, M., Ribeiro-Claro, P. & Gonçalves, I. S. (2008). Microporous Mesoporous Mater. 113, 453-462.]). Filyakova et al. (1996[Filyakova, V. I., Ratner, V. G., Karpenko, N. S. & Pashkevich, K. I. (1996). Russ. Chem. Bull. 45, 2278-2284.]).

[Scheme 1]

Experimental

Crystal data
  • C23H19N

  • Mr = 309.39

  • Triclinic, [P \overline 1]

  • a = 6.6304 (5) Å

  • b = 7.7772 (5) Å

  • c = 16.7587 (9) Å

  • [alpha] = 77.655 (3)°

  • [beta] = 87.969 (2)°

  • [gamma] = 85.734 (3)°

  • V = 841.69 (9) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.07 mm-1

  • T = 296 K

  • 0.17 × 0.07 × 0.04 mm

Data collection
  • Bruker X8 Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1998[Sheldrick, G. M. (1998). SADABS. Bruker AXS, Inc. Madison, Wisconsin, USA.]) Tmin = 0.988, Tmax = 0.997

  • 14750 measured reflections

  • 2986 independent reflections

  • 2021 reflections with I > 2[sigma](I)

  • Rint = 0.045

Refinement
  • R[F2 > 2[sigma](F2)] = 0.044

  • wR(F2) = 0.121

  • S = 1.02

  • 2986 reflections

  • 218 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.13 e Å-3

  • [Delta][rho]min = -0.16 e Å-3

Table 1
Selected short distance interactions (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the C18-C23, C3-C8 and C6-C12 rings, respectively,

D-H...A D-H H...A D...A D-H...A
C9-H9...Cg1i 0.93 3.00 3.5739 (18) 122
C16-H16...Cg2ii 0.93 2.84 3.5147 (18) 130
C17-H17...Cg3ii 0.93 2.84 3.5626 (19) 135
Symmetry codes: (i) -x, -y+1, -z+1; (ii) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2006[Bruker (2006). APEX2. Bruker AXS, Delft, The Netherlands.]); cell refinement: SAINT-Plus (Bruker, 2005[Bruker (2005). SAINT-Plus. Bruker AXS, Inc. Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg, 2009[Brandenburg, K. (2009). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NR2032 ).


Acknowledgements

We are grateful to the Fundação para a Ciência e a Tecnologia (FCT, Portugal), the European Union, QREN, FEDER, COMPETE and the Laboratório Associado Centro de Investigação em Materiais Cerâmicos e Compósitos, CICECO (PEst-C/CTM/LA0011/2011), for their general financial support. We further wish to thank the FCT for funding the R&D project PTDC/QUI-QUI/098098/2008 (FCOMP-01-0124-FEDER-010785), and for the post-doctoral research grants Nos. SFRH/BPD/63736/2009 (to JAF) and SFRH/BPD/46473/2008 (to SMB). Thanks are also due to the FCT for specific funding toward the purchase of the single-crystal diffractometer.

References

Brandenburg, K. (2009). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2005). SAINT-Plus. Bruker AXS, Inc. Madison, Wisconsin, USA.
Bruker (2006). APEX2. Bruker AXS, Delft, The Netherlands.
Bruno, S. M., Ferreira, R. A. S., Carlos, L. D., Pillinger, M., Ribeiro-Claro, P. & Gonçalves, I. S. (2008). Microporous Mesoporous Mater. 113, 453-462.  [ISI] [CrossRef] [ChemPort]
Filyakova, V. I., Ratner, V. G., Karpenko, N. S. & Pashkevich, K. I. (1996). Russ. Chem. Bull. 45, 2278-2284.  [CrossRef] [ISI]
Hampe, D., Günther, W., Görls, H. & Anders, E. (2004). Eur. J. Org. Chem. pp. 4357-4372.  [CSD] [CrossRef]
Kumar, A., Agarwal, M. & Singh, A. K. (2008). Polyhedron, 27, 485-492.  [ISI] [CSD] [CrossRef] [ChemPort]
Norton, D. G., Haury, V. E., Davis, F. C., Mitchell, L. J. & Ballard, S. A. (1954). J. Org. Chem. 19, 1054-1066.  [CrossRef]
Sheldrick, G. M. (1998). SADABS. Bruker AXS, Inc. Madison, Wisconsin, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2012). E68, o3143  [ doi:10.1107/S1600536812041414 ]

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