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Volume 69 
Part 5 
Page o717  
May 2013  

Received 27 February 2013
Accepted 9 April 2013
Online 13 April 2013

Key indicators
Single-crystal X-ray study
T = 190 K
Mean [sigma](C-C) = 0.002 Å
R = 0.047
wR = 0.124
Data-to-parameter ratio = 16.5
Details
Open access

3-Acetyl-2-methyl-4-(pyridin-3-yl)-1,4-dihydroindeno[1,2-b]pyridin-5-one

aLatvian Institute of Organic Synthesis, 21 Aizkraukles street, Riga LV-1006, Latvia
Correspondence e-mail: mishnevs@osi.lv

In the title compound, C20H16N2O2, the condensed tricyclic fragment is near to planar, with an r.m.s. deviation of 0.0531 Å. The 1,4-dihydropyridine (1,4-DHP) ring adopts a slightly puckered boat-like conformation. The N and opposite C atoms deviate from the least-squares plane of the four other ring atoms by 0.039 (3) and 0.141 (3) Å, respectively. The C=O group located at the tricyclic fragment is fixed in an s-trans orientation, while the second C=O group adopts an s-cis orientation with respect to the double bonds of the 1,4-DHP ring. The pyridine ring has a pseudo-axial orientation with respect to the 1,4-DHP ring. The dihedral angle between the tricyclic system and the pyridine ring is 77.3 (3)°. In the crystal, the pyridine N atom accepts a hydrogen bond from the N-H group of the 1,4-DHP ring. The hydrogen bonds link the molecules into infinite C(8) chains along the b-axis direction.

Related literature

For general information on the relationship between 1,4-dihydropyridine ring substituents and pharmaceutical effects, see: Christopher et al. (2010[Christopher, G. E., Umesh, K. J., Leah, N. M., Dickey, A. C. & Gestwicki, J. E. (2010). Chem. Commun. 47, 529-531.]); Bisenieks et al. (1987[Bisenieks, E. A., Uldrikis, J. R., Duburs, G. J., Kozuhov, A. N., Neimane, D. U., Ivanov, E. B. & Merkusev, G. N. (1987). USSR Inventors Certif. No. 1324260.], 1995[Bisenieks, E. A., Uldrikis, J. R., Duburs, G. J., Tirzitis, G. D., Dauvarte, A. D., Zidermane, A. A. & Ponomareva, A. B. (1995). USSR Inventors Certif. No. 1050261.]); Ivanov et al. (1989[Ivanov, E. I., Ponamareva, T. V., Merkushev, G. N., Duburs, G. J., Bisenieks, E. A., Uldrikis, J. R. & Makarova, N. V. (1989). Abstract Book of the IXth Soviet-Indian Symposium on the Chemistry of Natural Products, Riga, May 15-18, 1989, pp. 87-88.]). For the synthesis of 1,4-DHP-containing tricyclic derivatives, see: Bisenieks et al. (1982[Bisenieks, E. A., Uldrikis, J. R., Kirule, I. E., Tirzitis, G. D. & Duburs, G. J. (1982). Chem. Heterocycl. Compd, 18, 1187-1189.]).

[Scheme 1]

Experimental

Crystal data
  • C20H16N2O2

  • Mr = 316.35

  • Triclinic, [P \overline 1]

  • a = 8.4361 (3) Å

  • b = 8.8812 (3) Å

  • c = 11.2582 (4) Å

  • [alpha] = 87.692 (2)°

  • [beta] = 71.022 (2)°

  • [gamma] = 89.210 (2)°

  • V = 797.00 (5) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 190 K

  • 0.30 × 0.28 × 0.13 mm

Data collection
  • Nonius KappaCCD diffractometer

  • 5442 measured reflections

  • 3615 independent reflections

  • 2753 reflections with I > 2[sigma](I)

  • Rint = 0.020

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

  • wR(F2) = 0.124

  • S = 1.04

  • 3615 reflections

  • 219 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.23 e Å-3

  • [Delta][rho]min = -0.23 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1A...N22i 0.86 2.06 2.916 (2) 175
Symmetry code: (i) x, y+1, z.

Data collection: COLLECT (Hooft, 1998[Hooft, R. (1998). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: SCALEPACK (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: DENZO (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]) and SCALEPACK; 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.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FY2091 ).


Acknowledgements

The study was supported by the Latvian National Research Programme 2010-2013: "Development of prevention, treatment, diagnostic means, practices and biomedicine technologies for improvement of public health".

References

Bisenieks, E. A., Uldrikis, J. R., Duburs, G. J., Kozuhov, A. N., Neimane, D. U., Ivanov, E. B. & Merkusev, G. N. (1987). USSR Inventors Certif. No. 1324260.
Bisenieks, E. A., Uldrikis, J. R., Duburs, G. J., Tirzitis, G. D., Dauvarte, A. D., Zidermane, A. A. & Ponomareva, A. B. (1995). USSR Inventors Certif. No. 1050261.
Bisenieks, E. A., Uldrikis, J. R., Kirule, I. E., Tirzitis, G. D. & Duburs, G. J. (1982). Chem. Heterocycl. Compd, 18, 1187-1189.  [CrossRef]
Christopher, G. E., Umesh, K. J., Leah, N. M., Dickey, A. C. & Gestwicki, J. E. (2010). Chem. Commun. 47, 529-531.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Hooft, R. (1998). COLLECT. Nonius BV, Delft, The Netherlands.
Ivanov, E. I., Ponamareva, T. V., Merkushev, G. N., Duburs, G. J., Bisenieks, E. A., Uldrikis, J. R. & Makarova, N. V. (1989). Abstract Book of the IXth Soviet-Indian Symposium on the Chemistry of Natural Products, Riga, May 15-18, 1989, pp. 87-88.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o717  [ doi:10.1107/S1600536813009719 ]

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