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Volume 69 
Part 8 
Page o1289  
August 2013  

Received 8 July 2013
Accepted 16 July 2013
Online 20 July 2013

Key indicators
Single-crystal X-ray study
T = 125 K
Mean [sigma](C-C) = 0.002 Å
Disorder in main residue
R = 0.047
wR = 0.127
Data-to-parameter ratio = 21.9
Details
Open access

(E)-Benzyl(1-phenylethylidene)amine

aDepartment of Chemistry, Vassar College, Poughkeepsie, NY 12604, USA
Correspondence e-mail: jotanski@vassar.edu

The title compound, C15H15N, represents an E isomer. The molecule exhibits a minor [9.1 (2)%] disorder with methylbenzylidene and benzyl groups interchanging their positions. The C=N bond length is 1.292 (2) Å. The molecular geometry is essentially planar, with the maximal twist of 8.5 (3)° for the benzyl group. The herringbone packing arrangement does not exhibit any [pi]-stacking interactions.

Related literature

For information on the synthesis of (E)-benzyl(1-phenylethylidene)amine, see: Guthrie et al. (1973[Guthrie, R. D., Burdon, L. G. & Lovell, F. L. Jr (1973). J. Org. Chem. 38, 3114-3119.]); Willoughby & Buchwald (1994[Willoughby, C. A. & Buchwald, S. L. (1994). J. Am. Chem. Soc. 116, 8952-8965.]). For the crystal structures of similar imines, see: Bruno et al. (2012[Bruno, S. M., Fernandes, J. A., Gonçalves, I. S. & Almeida Paz, F. A. (2012). Acta Cryst. E68, o3143.]); Filarowski et al. (1999[Filarowski, A., Glowiaka, T. & Koll, A. (1999). J. Mol. Struct. 484, 75-89.]); Liu et al. (1997[Liu, Q., Ding, M., Lin, Y. & Xing, Y. (1997). J. Organomet. Chem. 548, 139-142.]).

[Scheme 1]

Experimental

Crystal data
  • C15H15N

  • Mr = 209.28

  • Monoclinic, P 21 /n

  • a = 5.4633 (4) Å

  • b = 10.4173 (8) Å

  • c = 20.2426 (15) Å

  • [beta] = 97.308 (1)°

  • V = 1142.71 (15) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.07 mm-1

  • T = 125 K

  • 0.32 × 0.21 × 0.03 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: empirical (using intensity measurements) (SADABS; Bruker, 2007[Bruker (2007). SAINT, SADABS and APEX2. Bruxer AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.978, Tmax = 0.998

  • 18404 measured reflections

  • 3496 independent reflections

  • 2509 reflections with I > 2[sigma](I)

  • Rint = 0.042

Refinement
  • R[F2 > 2[sigma](F2)] = 0.047

  • wR(F2) = 0.127

  • S = 1.03

  • 3496 reflections

  • 160 parameters

  • 105 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.34 e Å-3

  • [Delta][rho]min = -0.20 e Å-3

Data collection: APEX2 (Bruker, 2007[Bruker (2007). SAINT, SADABS and APEX2. Bruxer AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). SAINT, SADABS and APEX2. Bruxer AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL, OLEX2 (Dolomanov, et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]) and Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LD2110 ).


Acknowledgements

This work was supported by Vassar College. X-ray facilities were provided by the US National Science Foundation (grant No. 0521237 to JMT).

References

Bruker (2007). SAINT, SADABS and APEX2. Bruxer AXS Inc., Madison, Wisconsin, USA.
Bruno, S. M., Fernandes, J. A., Gonçalves, I. S. & Almeida Paz, F. A. (2012). Acta Cryst. E68, o3143.  [CSD] [CrossRef] [IUCr Journals]
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Filarowski, A., Glowiaka, T. & Koll, A. (1999). J. Mol. Struct. 484, 75-89.  [Web of Science] [CrossRef] [ChemPort]
Guthrie, R. D., Burdon, L. G. & Lovell, F. L. Jr (1973). J. Org. Chem. 38, 3114-3119.  [CrossRef] [ChemPort]
Liu, Q., Ding, M., Lin, Y. & Xing, Y. (1997). J. Organomet. Chem. 548, 139-142.  [CrossRef] [ChemPort]
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Willoughby, C. A. & Buchwald, S. L. (1994). J. Am. Chem. Soc. 116, 8952-8965.  [CrossRef] [ChemPort] [Web of Science]


Acta Cryst (2013). E69, o1289  [ doi:10.1107/S1600536813019636 ]

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