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Volume 69 
Part 12 
Pages o1816-o1817  
December 2013  

Received 8 November 2013
Accepted 18 November 2013
Online 23 November 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.046
wR = 0.143
Data-to-parameter ratio = 17.0
Details
Open access

6-(4-Amino­phen­yl)-2-meth­oxy-4-phenyl­nicotino­nitrile

aDepartment of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, and bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
Correspondence e-mail: suchada.c@psu.ac.th

In the structure of the title nicotino­nitrile derivative, C19H15N3O, the pyridine ring makes dihedral angles of 11.50 (7) and 43.36 (8)° with the 4-amino­phenyl and phenyl rings, respectively, and the dihedral angle between the phenyl rings is 36.28°. In the crystal, mol­ecules are linked by N-H...N hydrogen bonds into wave-like sheets parallel to (10-2). These sheets are stacked by [pi]-[pi] inter­actions between the 4-amino­phenyl rings of adjacent sheets, with centroid-centroid distances of 3.7499 (9) Å. C-H...[pi] inter­actions are also present.

Related literature

For the synthesis and applications of nicotino­nitrile derivatives, see: Al-Jaber et al. (2012[Al-Jaber, N. A., Bougasim, A. S. A. & Karah, M. M. S. (2012). J. Saudi Chem. Soc. 16, 45-53.]); Brandt et al. (2010[Brandt, W., Mologni, L., Preu, L., Lemcke, T., Gambacorti-Passerini, C. & Kunick, C. (2010). Eur. J. Med. Chem. 45, 2919-2927.]); El-Sayed et al. (2011[El-Sayed, H. A., Moustafa, A. H., Haikal, A. E.-F. Z., Abu-El-Halawa, R. & Ashry, E. S. H. E. (2011). Eur. J. Med. Chem. 46, 2948-2954.]); Ji et al. (2007[Ji, J., Bunnelle, W. H., Anderson, D. J., Faltynek, C., Dyhring, T., Ahring, P. K., Rueter, L. E., Curzon, P., Buckley, M. J., Marsh, K. C., Kempf-Grote, A. & Meyer, M. D. (2007). Biochem. Pharmacol. 74, 1253-1262.]); Kim et al. (2005[Kim, K.-R., Rhee, S.-D., Kim, H. Y., Jung, W. H., Yang, S.-D., Kim, S. S., Ahn, J. H. & Cheon, H. G. (2005). Eur. J. Pharmacol. 518, 63-70.]); Koner et al. (2012[Koner, R. R., Sinha, S., Kumar, S., Nandi, C. K. & Ghosh, S. (2012). Tetrahedron Lett. 53, 2302-2307.]); Raghukumar et al. (2003[Raghukumar, V., Thirumalai, D., Ramakrishnan, V. T., Karunakara, V. & Ramamurthy, P. (2003). Tetrahedron, 59, 3761-3768.]); Zhou et al. (2006[Zhou, W.-J., Ji, S.-J. & Shen, Z.-L. (2006). J. Organomet. Chem. 691, 1356-1360.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). For related structures, see: Chantrapromma et al. (2013[Chantrapromma, S., Suwunwong, T., Ruanwas, P., Quah, C. K. & Fun, H.-K. (2013). Acta Cryst. E69, o1500-o1501.]); Suwunwong et al. (2012[Suwunwong, T., Chantrapromma, S. & Fun, H.-K. (2012). Acta Cryst. E68, o2812-o2813.], 2013[Suwunwong, T., Chantrapromma, S. & Fun, H.-K. (2013). J. Chem. Crystallogr. 43, 538-543.]).

[Scheme 1]

Experimental

Crystal data
  • C19H15N3O

  • Mr = 301.34

  • Monoclinic, P 21 /c

  • a = 10.9448 (12) Å

  • b = 18.960 (2) Å

  • c = 7.4738 (8) Å

  • [beta] = 94.743 (2)°

  • V = 1545.6 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 100 K

  • 0.56 × 0.17 × 0.06 mm

Data collection
  • Bruker APEX DUO CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.955, Tmax = 0.995

  • 14200 measured reflections

  • 3696 independent reflections

  • 2689 reflections with I > 2[sigma](I)

  • Rint = 0.051

Refinement
  • R[F2 > 2[sigma](F2)] = 0.046

  • wR(F2) = 0.143

  • S = 1.07

  • 3696 reflections

  • 217 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.30 e Å-3

  • [Delta][rho]min = -0.28 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 and Cg3 are the centroids of the C1-C6 and C10-C15 rings, respectively.

D-H...A D-H H...A D...A D-H...A
N1-H2N1...N3i 0.915 (19) 2.338 (19) 3.2416 (18) 169.5 (19)
N1-H1N1...N3ii 0.91 (2) 2.28 (2) 3.1773 (19) 168 (2)
C11-H11A...Cg3iii 0.95 2.87 3.7667 (17) 158
C19-H19C...Cg2iv 0.98 2.69 3.5156 (17) 142
Symmetry codes: (i) [x+1, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (ii) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) [x, -y-{\script{1\over 2}}, z-{\script{1\over 2}}]; (iv) [x, -y-{\script{1\over 2}}, z-{\script{3\over 2}}].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: SHELXTL; software used to prepare material for publication: SHELXTL, PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]), 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.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ5368 ).


Acknowledgements

TS and SC thank the Thailand Research Fund through the Royal Golden Jubilee PhD Program (grant No. PHD/0257/2553) for financial support. The authors extend their appreciation to the Prince of Songkla University and the Universiti Sains Malaysia for the APEX DE2012 grant No. 1002/PFIZIK/910323.

References

Al-Jaber, N. A., Bougasim, A. S. A. & Karah, M. M. S. (2012). J. Saudi Chem. Soc. 16, 45-53.  [ChemPort]
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Brandt, W., Mologni, L., Preu, L., Lemcke, T., Gambacorti-Passerini, C. & Kunick, C. (2010). Eur. J. Med. Chem. 45, 2919-2927.  [Web of Science] [CrossRef] [ChemPort] [PubMed]
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Chantrapromma, S., Suwunwong, T., Ruanwas, P., Quah, C. K. & Fun, H.-K. (2013). Acta Cryst. E69, o1500-o1501.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
El-Sayed, H. A., Moustafa, A. H., Haikal, A. E.-F. Z., Abu-El-Halawa, R. & Ashry, E. S. H. E. (2011). Eur. J. Med. Chem. 46, 2948-2954.  [Web of Science] [ChemPort] [PubMed]
Ji, J., Bunnelle, W. H., Anderson, D. J., Faltynek, C., Dyhring, T., Ahring, P. K., Rueter, L. E., Curzon, P., Buckley, M. J., Marsh, K. C., Kempf-Grote, A. & Meyer, M. D. (2007). Biochem. Pharmacol. 74, 1253-1262.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Kim, K.-R., Rhee, S.-D., Kim, H. Y., Jung, W. H., Yang, S.-D., Kim, S. S., Ahn, J. H. & Cheon, H. G. (2005). Eur. J. Pharmacol. 518, 63-70.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Koner, R. R., Sinha, S., Kumar, S., Nandi, C. K. & Ghosh, S. (2012). Tetrahedron Lett. 53, 2302-2307.  [Web of Science] [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]
Raghukumar, V., Thirumalai, D., Ramakrishnan, V. T., Karunakara, V. & Ramamurthy, P. (2003). Tetrahedron, 59, 3761-3768.  [Web of Science] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Suwunwong, T., Chantrapromma, S. & Fun, H.-K. (2012). Acta Cryst. E68, o2812-o2813.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Suwunwong, T., Chantrapromma, S. & Fun, H.-K. (2013). J. Chem. Crystallogr. 43, 538-543.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Zhou, W.-J., Ji, S.-J. & Shen, Z.-L. (2006). J. Organomet. Chem. 691, 1356-1360.  [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o1816-o1817   [ doi:10.1107/S1600536813031437 ]

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