[Journal logo]

Volume 69 
Part 5 
Page o780  
May 2013  

Received 2 April 2013
Accepted 18 April 2013
Online 24 April 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.050
wR = 0.152
Data-to-parameter ratio = 23.3
Details
Open access

(Z)-3-(2-Aminoanilino)-1-phenylbut-2-en-1-one

aCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India, and bDepartment of Inorganic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India
Correspondence e-mail: shirai2011@gmail.com

In the title compound, C16H16N2O, the phenyl and 2-aminophenyl rings are almost perpendicular to one another, with a dihedral angle of 82.77 (8)°. There is an intramolecular N-H...O hydrogen bond in the molecule. In the crystal, molecules are linked via N-H...O hydrogen bonds forming chains along [001]. There are also C-H...[pi] interactions present, linking the chains to form a three-dimensional structure.

Related literature

For the biological activity of chalcones, see: Di Carlo et al. (1999[Di Carlo, G., Mascolo, N., Izzo, A. A. & Capasso, F. (1999). Life Sci. 65, 337-353.]); Lin et al. (2002[Lin, Y. M., Zhou, Y., Flavin, M. T., Zhou, L. M., Nie, W. & Chen, F. C. (2002). Bioorg. Med. Chem. 10, 2795-2802.]). For a related chalcone structure, see: Ranjith et al. (2010[Ranjith, S., Thirunarayanan, A., Raja, S., Rajakumar, P. & SubbiahPandi, A. (2010). Acta Cryst. E66, o2261-o2262.]).

[Scheme 1]

Experimental

Crystal data
  • C16H16N2O

  • Mr = 252.31

  • Monoclinic, C 2/c

  • a = 15.489 (5) Å

  • b = 16.422 (5) Å

  • c = 11.684 (5) Å

  • [beta] = 110.646 (5)°

  • V = 2781.1 (17) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 293 K

  • 0.30 × 0.25 × 0.20 mm

Data collection
  • Bruker SMART APEXII area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.977, Tmax = 0.985

  • 18172 measured reflections

  • 4023 independent reflections

  • 2805 reflections with I > 2[sigma](I)

  • Rint = 0.028

Refinement
  • R[F2 > 2[sigma](F2)] = 0.050

  • wR(F2) = 0.152

  • S = 1.01

  • 4023 reflections

  • 173 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.30 e Å-3

  • [Delta][rho]min = -0.22 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of ring C1-C6.

D-H...A D-H H...A D...A D-H...A
N2-H2A...O1 0.86 1.95 2.6311 (19) 135
N1-H1A...O1i 0.86 2.28 3.001 (2) 142
N1-H1B...O1ii 0.86 2.18 3.034 (2) 174
C14-H14...Cg1iii 0.93 2.96 3.773 (3) 147
Symmetry codes: (i) [-x+2, y, -z+{\script{1\over 2}}]; (ii) [x, -y, z+{\script{1\over 2}}]; (iii) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker 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: 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: SU2583 ).


Acknowledgements

TS and DV thank the TBI X-ray facility, CAS in Crystallography and Biophysics, University of Madras, India, for data collection and UGC (SAP-CAS) is acknowledged for departmental facilities. TS thanks DST for the Inspire Fellowship.

References

Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Di Carlo, G., Mascolo, N., Izzo, A. A. & Capasso, F. (1999). Life Sci. 65, 337-353.  [ISI] [CrossRef] [PubMed] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Lin, Y. M., Zhou, Y., Flavin, M. T., Zhou, L. M., Nie, W. & Chen, F. C. (2002). Bioorg. Med. Chem. 10, 2795-2802.  [CrossRef] [PubMed] [ChemPort]
Ranjith, S., Thirunarayanan, A., Raja, S., Rajakumar, P. & SubbiahPandi, A. (2010). Acta Cryst. E66, o2261-o2262.  [CSD] [CrossRef] [ChemPort] [details]
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]


Acta Cryst (2013). E69, o780  [ doi:10.1107/S160053681301060X ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.