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Volume 69 
Part 6 
Page o905  
June 2013  

Received 29 April 2013
Accepted 7 May 2013
Online 18 May 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.004 Å
R = 0.061
wR = 0.187
Data-to-parameter ratio = 16.1
Details
Open access

N-[4-(Dimethylamino)benzylidene]-4-methylaniline

aCentre for Crystal Growth, School of Advanced Sciences, VIT University, Vellore 632 014, India,bSophisticated Test and Instrumentation Centre (STIC), Cochin University PO, Cochin 682 022, Kerala, and cDepartment of Physics, Bangladesh University of Engineering and Technology, Dhaka 1000, Bangladesh
Correspondence e-mail: jpodder59@gmail.com

The molecules of the title compound, C16H18N2, exists in a trans conformation with respect to the C=N bond [1.270 (3) Å]. The least-squares plane of the dimethylamino group makes a dihedral angle of 1.3 (2)° with the ring to which it is attached. The dihedral angle between the two aromatic rings is 11.70 (2)°. The crystal structure features weak C-H...[pi] interactions.

Related literature

For the uses and biological importance of diketones, see: Xia et al. (2009[Xia, D.-G., Ye, Y.-F. & Lei, K.-W. (2009). Acta Cryst. E65, o3168.]); Shah et al. (1992[Shah, S., Vyas, R. & Mehta, R. H. (1992). J. Indian Chem. Soc. 69, 590-590.]); Ünver et al. (2004[Ünver, H., Karakas, A. & Elmali, A. (2004). J. Mol. Struct. 702, 49-54.]). For related structures, see: Fun et al. (2011[Fun, H.-K., Quah, C. K., Huang, C. & Yu, H. (2011). Acta Cryst. E67, o1273-o1274.]); Khalaji & Simpson (2009[Khalaji, A. D. & Simpson, J. (2009). Acta Cryst. E65, o553.]).

[Scheme 1]

Experimental

Crystal data
  • C16H18N2

  • Mr = 238.32

  • Orthorhombic, P b c a

  • a = 10.4814 (10) Å

  • b = 8.0528 (8) Å

  • c = 32.571 (3) Å

  • V = 2749.1 (4) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.07 mm-1

  • T = 296 K

  • 0.30 × 0.25 × 0.20 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2004[Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.980, Tmax = 0.987

  • 17121 measured reflections

  • 2692 independent reflections

  • 1737 reflections with I > 2[sigma](I)

  • Rint = 0.041

Refinement
  • R[F2 > 2[sigma](F2)] = 0.061

  • wR(F2) = 0.187

  • S = 1.08

  • 2692 reflections

  • 167 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.21 e Å-3

  • [Delta][rho]min = -0.16 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C11-H11...Cg1i 0.93 2.94 3.670 (2) 137
Symmetry code: (i) [x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT (Bruker, 2004[Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT and XPREP (Bruker, 2004[Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to solve structure: SIR92 (Altomare et al., 1993[Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT6904 ).


Acknowledgements

The author acknowledges the STIC, Cochin 682 022, for the single-crystal XRD facility. The authors also thank Mr P. Narayanan and Dr K·Sethusankar, RKM Vivekananda College (Autonomous), Chennai 600 004, and VIT University for providing the excellent research facilities.

References

Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.  [CrossRef] [ISI] [details]
Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Fun, H.-K., Quah, C. K., Huang, C. & Yu, H. (2011). Acta Cryst. E67, o1273-o1274.  [CSD] [CrossRef] [ChemPort] [details]
Khalaji, A. D. & Simpson, J. (2009). Acta Cryst. E65, o553.  [CSD] [CrossRef] [details]
Shah, S., Vyas, R. & Mehta, R. H. (1992). J. Indian Chem. Soc. 69, 590-590.  [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]
Ünver, H., Karakas, A. & Elmali, A. (2004). J. Mol. Struct. 702, 49-54.
Xia, D.-G., Ye, Y.-F. & Lei, K.-W. (2009). Acta Cryst. E65, o3168.  [CSD] [CrossRef] [details]


Acta Cryst (2013). E69, o905  [ doi:10.1107/S160053681301249X ]

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