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Volume 69 
Part 10 
Pages o1500-o1501  
October 2013  

Received 2 August 2013
Accepted 26 August 2013
Online 4 September 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.042
wR = 0.116
Data-to-parameter ratio = 20.2
Details
Open access

6-Methoxy-4-(2,4,5-trimethoxyphenyl)-2,2'-bipyridine-5-carbonitrile

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 title 3-cyanopyridine derivative, C21H19N3O4, the 3-cyano-substituted pyridine ring forms dihedral angles of 2.35 (5) and 41.60 (5)° with the unsubstituted pyridine and 2,4,5-trimethoxy-substituted benzene rings, respectively. The dihedral angle between the unsubstituted pyridine and benzene rings is 39.84 (5)°. The methoxy groups form Cmethyl-O-C-(C,N) torsion angles in the range 0.80 (15)-11.45 (15)°. In the crystal, molecules related by 21 screw axes are linked by weak C-H...N hydrogen bonds along [010]. In addition, weak C-H...[pi] interactions and [pi]-[pi] stacking interactions between pyridine rings, with a centroid-centroid distance of 3.6448 (6) Å, are observed.

Related literature

For the synthesis and applications of 3-cyanopyridine 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.]); Suwunwong et al. (2011[Suwunwong, T., Chantrapromma, S. & Fun, H.-K. (2011). Chem. Pap. 65, 890-897.]); Zhou et al. (2006[Zhou, W.-J., Ji, S.-J. & Shen, Z.-L. (2006). J. Organomet. Chem. 691, 1356-1360.]). For related structures, see: Chantrapromma et al. (2010[Chantrapromma, S., Fun, H.-K., Suwunwong, T., Padaki, M. & Isloor, A. M. (2010). Acta Cryst. E66, o79-o80.]); Suwunwong et al. (2012[Suwunwong, T., Chantrapromma, S. & Fun, H.-K. (2012). Acta Cryst. E68, o2812-o2813.]). For standard 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.]).

[Scheme 1]

Experimental

Crystal data
  • C21H19N3O4

  • Mr = 377.39

  • Monoclinic, P 21 /c

  • a = 14.9967 (3) Å

  • b = 7.4039 (2) Å

  • c = 17.5795 (4) Å

  • [beta] = 114.080 (1)°

  • V = 1782.06 (7) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 100 K

  • 0.60 × 0.29 × 0.23 mm

Data collection
  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.943, Tmax = 0.977

  • 20323 measured reflections

  • 5182 independent reflections

  • 4386 reflections with I > 2[sigma](I)

  • Rint = 0.030

Refinement
  • R[F2 > 2[sigma](F2)] = 0.042

  • wR(F2) = 0.116

  • S = 1.03

  • 5182 reflections

  • 257 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.40 e Å-3

  • [Delta][rho]min = -0.31 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C11-C16 ring.

D-H...A D-H H...A D...A D-H...A
C20-H20C...N3i 0.98 2.59 3.3774 (17) 138
C1-H1A...Cg3ii 0.95 2.89 3.7062 (13) 145
Symmetry codes: (i) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). 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: LH5641 ).


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 thank 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 (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Chantrapromma, S., Fun, H.-K., Suwunwong, T., Padaki, M. & Isloor, A. M. (2010). Acta Cryst. E66, o79-o80.  [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]
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. (2011). Chem. Pap. 65, 890-897.  [CSD] [CrossRef] [ChemPort]
Suwunwong, T., Chantrapromma, S. & Fun, H.-K. (2012). Acta Cryst. E68, o2812-o2813.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
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, o1500-o1501   [ doi:10.1107/S1600536813023891 ]

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