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Volume 69 
Part 6 
Page o956  
June 2013  

Received 18 April 2013
Accepted 20 May 2013
Online 25 May 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.005 Å
R = 0.060
wR = 0.119
Data-to-parameter ratio = 17.0
Details
Open access

2-(4-Bromophenyl)-4-(4-methoxyphenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine

aDepartment of Physics, Faculty of Sciences, Cumhuriyet University, 58140 Sivas, Turkey,bDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey,cDepartment of Physics, Faculty of Arts and Sciences, Gaziosmanpasa University, 60240 Tokat, Turkey, and dDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayis University, 55139 Samsun, Turkey
Correspondence e-mail: icelik@cumhuriyet.edu.tr

In the title compound, C23H22BrNO, the cycloheptane ring adopts a chair conformation. The pyridine ring makes dihedral angles of 58.63 (15) and 8.27 (16)° with the benzene rings. The dihedral angle between the benzene rings is 56.68 (17)°. The crystal packing features C-Br...[pi] interactions [Br...centroid distances= 3.813 (2) and 3.839 (2) Å; C-Br...centroid = 126.25 (10) and 138.31 (10)°, respectively, forming a three dimensional supramolecular architecture.

Related literature

For the biological and pharmacological properties of pyridine-based heterocycles, see: Aida et al. (2009[Aida, W., Ohtsuki, T., Li, X. & Ishibashi, M. (2009). Tetrahedron, 65, 369-373.]); Ceylan & Gezegen (2008[Ceylan, N. M. & Gezegen, H. (2008). Turk. J. Chem. 32, 55-61.]); Cundy et al. (1997[Cundy, D. J., Holan, G., Otaegui, M. & Simpson, G. W. (1997). Bioorg. Med. Chem. Lett. 7, 669-674.]); El-borai et al. (2012[El-borai, M. A., Rizk, H. F., Abd-Aal, M. F. & El-Deeb, I. Y. (2012). Eur. J. Med. Chem. 48, 92-96.]); Gezegen et al. (2010[Gezegen, H., Dingil, A. & Ceylan, M. (2010). J. Heterocycl. Chem. 47, 1017-1024.]); Girgis et al. (2007[Girgis, A. S., Mishriky, N., Ellithey, M., Hosni, H. M. & Farag, H. (2007). Bioorg. Med. Chem. 15, 2403-2413.]); Hatanaka et al. (2005[Hatanaka, M., Takahashi, K., Nakamura, S. & Mashino, T. (2005). Bioorg. Med. Chem. 13, 6763-6770.]); Khidre et al. (2011[Khidre, R. E., Abu-Hashem, A. A. & El-Shazly, M. (2011). Eur. J. Med. Chem. 46, 5057-5064.]); Laine-Cessac et al. (1997[Laine-Cessac, P., Cailleux, A. & Allain, P. (1997). Biochem. Pharmacol. 54, 863-870.]); Menegatti et al. (2006[Menegatti, R., Silva, G. M. S., Zapata-Sudo, G., Raimundo, J. M., Sudo, R. T., Barreiro, E. J. & Fraga, C. A. M. (2006). Bioorg. Med. Chem. 14, 632-640.]); Musiol et al. (2007[Musiol, R., Jampilek, J., Kralova, K., Richardson, D. R., Kalinowski, D., Podeszwa, B., Finster, J., Niedbala, H., Palka, A. & Polanski, J. (2007). Bioorg. Med. Chem. 105, 1280-1288.]); Rajanarendar et al. (2012[Rajanarendar, E., Raju, S., Reddy, M. N., Krishna, S. R., Kiran, L. H., Reddy, A. R. N. & Reddy, Y. N. (2012). Eur. J. Med. Chem. 50, 274-279.]). For ring conformation analysis, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C23H22BrNO

  • Mr = 408.32

  • Monoclinic, P 21 /c

  • a = 10.409 (5) Å

  • b = 10.054 (5) Å

  • c = 18.428 (5) Å

  • [beta] = 94.850 (5)°

  • V = 1921.6 (14) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 2.15 mm-1

  • T = 296 K

  • 0.58 × 0.42 × 0.26 mm

Data collection
  • Stoe IPDS 2 diffractometer

  • Absorption correction: integration (X-RED32; Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]) Tmin = 0.355, Tmax = 0.572

  • 28207 measured reflections

  • 3986 independent reflections

  • 3083 reflections with I > 2[sigma](I)

  • Rint = 0.178

Refinement
  • R[F2 > 2[sigma](F2)] = 0.060

  • wR(F2) = 0.119

  • S = 1.12

  • 3986 reflections

  • 235 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.67 e Å-3

  • [Delta][rho]min = -0.42 e Å-3

Data collection: X-AREA (Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]); 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: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) 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: RZ5059 ).


Acknowledgements

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayis University, Turkey, for the use of the Stoe IPDS 2 diffractometer (purchased under grant F.279 of the University Research Fund).

References

Aida, W., Ohtsuki, T., Li, X. & Ishibashi, M. (2009). Tetrahedron, 65, 369-373.  [ISI] [CrossRef] [ChemPort]
Ceylan, N. M. & Gezegen, H. (2008). Turk. J. Chem. 32, 55-61.  [ChemPort]
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Cundy, D. J., Holan, G., Otaegui, M. & Simpson, G. W. (1997). Bioorg. Med. Chem. Lett. 7, 669-674.  [CrossRef] [ChemPort]
El-borai, M. A., Rizk, H. F., Abd-Aal, M. F. & El-Deeb, I. Y. (2012). Eur. J. Med. Chem. 48, 92-96.  [ISI] [ChemPort] [PubMed]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Gezegen, H., Dingil, A. & Ceylan, M. (2010). J. Heterocycl. Chem. 47, 1017-1024.  [CrossRef] [ChemPort]
Girgis, A. S., Mishriky, N., Ellithey, M., Hosni, H. M. & Farag, H. (2007). Bioorg. Med. Chem. 15, 2403-2413.  [CSD] [CrossRef] [PubMed] [ChemPort]
Hatanaka, M., Takahashi, K., Nakamura, S. & Mashino, T. (2005). Bioorg. Med. Chem. 13, 6763-6770.  [CrossRef] [PubMed] [ChemPort]
Khidre, R. E., Abu-Hashem, A. A. & El-Shazly, M. (2011). Eur. J. Med. Chem. 46, 5057-5064.  [ISI] [CrossRef] [ChemPort] [PubMed]
Laine-Cessac, P., Cailleux, A. & Allain, P. (1997). Biochem. Pharmacol. 54, 863-870.  [ChemPort] [PubMed] [ISI]
Menegatti, R., Silva, G. M. S., Zapata-Sudo, G., Raimundo, J. M., Sudo, R. T., Barreiro, E. J. & Fraga, C. A. M. (2006). Bioorg. Med. Chem. 14, 632-640.  [CrossRef] [PubMed] [ChemPort]
Musiol, R., Jampilek, J., Kralova, K., Richardson, D. R., Kalinowski, D., Podeszwa, B., Finster, J., Niedbala, H., Palka, A. & Polanski, J. (2007). Bioorg. Med. Chem. 105, 1280-1288.  [CrossRef]
Rajanarendar, E., Raju, S., Reddy, M. N., Krishna, S. R., Kiran, L. H., Reddy, A. R. N. & Reddy, Y. N. (2012). Eur. J. Med. Chem. 50, 274-279.  [ISI] [CrossRef] [ChemPort] [PubMed]
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]
Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.


Acta Cryst (2013). E69, o956  [ doi:10.1107/S1600536813013913 ]

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