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Volume 69 
Part 11 
Pages o1651-o1652  
November 2013  

Received 30 August 2013
Accepted 10 October 2013
Online 16 October 2013

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.004 Å
R = 0.065
wR = 0.226
Data-to-parameter ratio = 13.3
Details
Open access

(E)-2-[2-(3-Nitro­phen­yl)ethen­yl]quinolin-8-ol

aInstitut für Organische Chemie, TU Bergakademie Freiberg, Leipziger Strasse 29, D-09596 Freiberg/Sachsen, Germany
Correspondence e-mail: edwin.weber@chemie.tu-freiberg.de

In the title compound, C17H12N2O3, the mean planes of the benzene ring and the quinoline moiety are inclined to one another by 11.0 (1)°. The nitro substituent is twisted at an angle of 7.9 (2)° with respect to the attached benzene ring. Intra­molecular O-H...N and C-H...N hydrogen bonds occur. The crystal is constructed of mol­ecular stacks without involvement of [pi]-stacking inter­actions, but showing inter­stack association via O-H...O and C-H...O hydrogen bonding. Thus, the supramolecular architecture of the crystal results from stacked molecules stabilized by hydrogen bonding between the stacks.

Related literature

For uses of quinolin-8-ol and derivatives as complexants and pharmaceuticals, see: Albrecht et al. (2008[Albrecht, M., Fiege, M. & Osetska, O. (2008). Coord. Chem. Rev. 252, 812-824.]); Cacciatore et al. (2013[Cacciatore, I., Fornasari, E., Baldassarre, L., Cornacchia, C., Fulle, S., Di Filippo, E. S., Pietrangelo, T. & Pinnen, F. (2013). Pharmaceuticals, 6, 54-69.]); Desvignes & Leguen (1963[Desvignes, A. & Leguen, P. (1963). Ann. Pharm. Fr. 21, 803-808.]); McMaster & Bruner (1935[McMaster, L. & Bruner, W. M. (1935). J. Am. Chem. Soc. 57, 1997-1998.]); Vögtle & Weber (1979[Vögtle, F. & Weber, E. (1979). Angew. Chem. Int. Ed. 18, 753-776.]); Weber & Vögtle (1975[Weber, E. & Vögtle, F. (1975). Tetrahedron Lett. pp. 2415-2418.]). For applications of stilbene and derivatives, see: Butkovic et al. (2011[Butkovic, K., Marinic, Z., Molcanov, K., Kojic-Prodic, B. & Sindler-Kulyk, M. (2011). Beilstein J. Org. Chem. 7, 1663-1670.]); Ho et al. (2000[Ho, T.-J., Ho, J.-H. & Wu, J. Y. (2000). J. Am. Chem. Soc. 122, 8575-8576.]); Navadiya et al. (2008[Navadiya, H. D., Undavia, N. K. & Patwa, B. S. (2008). Int. J. Chem. Sci. 6, 2224-2232.]); Ravikrishnan et al. (2012[Ravikrishnan, A., Sudhakara, P. & Kannan, P. (2012). J. Mater. Sci. 45, 435-442.]); Waibel et al. (2009[Waibel, M., De Angelis, M., Stossi, F., Kieser, K. J., Carlson, K. E., Katzenellenbogen, B. S. & Katzenellenbogen, J. A. (2009). Eur. J. Med. Chem. 44, 3412-3424.]); Zhu et al. (2013[Zhu, Y.-C., Lu, H.-X., He, D. H. & Yang, Z.-R. (2013). J. Photochem. Photobiol. B, 125, 8-12.]). For the preparative method used for the synthesis of the title compound, see: Yuan et al. (2012[Yuan, G.-Z., Rong, L.-L., Huo, Y.-P., Nie, X.-L. & Fang, X.-M. (2012). Inorg. Chem. Commun. 23, 90-94.]). For non-classical hydrogen bonds, see: Desiraju & Steiner (1999[Desiraju, G. R. & Steiner, T. (1999). The Weak Hydrogen Bond in Structural Chemistry and Biology, ch. 2. Oxford University Press.]). For related structures, including intra­molecular hydrogen bonding of quinolin-8-ol, see: Faza­eli et al. (2008[Fazaeli, Y., Amini, M. M., Gao, S. & Ng, S. W. (2008). Acta Cryst. E64, o97.]); Malecki et al. (2010[Malecki, G., Nycz, J. E., Ryrych, E., Pomikiewski, L., Nowak, M., Kusz, J. & Pikies, J. (2010). J. Mol. Struct. 969, 130-138.]); Yoneda et al. (2002[Yoneda, S., Ohfuchi, S., Hashimoto, A. & Kitamura, C. (2002). Kenkyu Hokuku Himeji Kogyo Daigaku, 54, 60-67.]); Zeng et al. (2007[Zeng, H.-P., Wang, T.-T., Xu, D.-F., Cai, Y.-P. & Chen, D.-F. (2007). J. Appl. Cryst. 40, 471-475.]).

[Scheme 1]

Experimental

Crystal data
  • C17H12N2O3

  • Mr = 292.29

  • Monoclinic, P 21 /c

  • a = 20.3346 (7) Å

  • b = 4.7167 (1) Å

  • c = 15.5674 (6) Å

  • [beta] = 109.255 (2)°

  • V = 1409.58 (8) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 298 K

  • 0.54 × 0.24 × 0.06 mm

Data collection
  • Bruker X8 APEXII CCD detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2007[Bruker (2007). SAINT-NT, SMART and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.950, Tmax = 0.994

  • 22418 measured reflections

  • 2655 independent reflections

  • 1768 reflections with I > 2[sigma](I)

  • Rint = 0.028

Refinement
  • R[F2 > 2[sigma](F2)] = 0.065

  • wR(F2) = 0.226

  • S = 1.03

  • 2655 reflections

  • 200 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.42 e Å-3

  • [Delta][rho]min = -0.24 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...N1 0.82 2.19 2.657 (3) 117
O1-H1...O2i 0.82 2.53 3.180 (5) 137
C10-H10...O1ii 0.93 2.51 3.400 (3) 160
C11-H11...N1 0.93 2.53 2.857 (4) 101
Symmetry codes: (i) [x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]; (ii) [x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}].

Data collection: SMART (Bruker, 2007[Bruker (2007). SAINT-NT, SMART and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-NT (Bruker, 2007[Bruker (2007). SAINT-NT, SMART and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-NT; 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RN2119 ).


References

Albrecht, M., Fiege, M. & Osetska, O. (2008). Coord. Chem. Rev. 252, 812-824.  [Web of Science] [CrossRef] [ChemPort]
Bruker (2007). SAINT-NT, SMART and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Butkovic, K., Marinic, Z., Molcanov, K., Kojic-Prodic, B. & Sindler-Kulyk, M. (2011). Beilstein J. Org. Chem. 7, 1663-1670.  [ChemPort] [PubMed]
Cacciatore, I., Fornasari, E., Baldassarre, L., Cornacchia, C., Fulle, S., Di Filippo, E. S., Pietrangelo, T. & Pinnen, F. (2013). Pharmaceuticals, 6, 54-69.  [CrossRef] [ChemPort]
Desiraju, G. R. & Steiner, T. (1999). The Weak Hydrogen Bond in Structural Chemistry and Biology, ch. 2. Oxford University Press.
Desvignes, A. & Leguen, P. (1963). Ann. Pharm. Fr. 21, 803-808.  [PubMed] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Fazaeli, Y., Amini, M. M., Gao, S. & Ng, S. W. (2008). Acta Cryst. E64, o97.  [CSD] [CrossRef] [IUCr Journals]
Ho, T.-J., Ho, J.-H. & Wu, J. Y. (2000). J. Am. Chem. Soc. 122, 8575-8576.  [Web of Science] [CrossRef] [ChemPort]
Malecki, G., Nycz, J. E., Ryrych, E., Pomikiewski, L., Nowak, M., Kusz, J. & Pikies, J. (2010). J. Mol. Struct. 969, 130-138.  [Web of Science] [CrossRef] [ChemPort]
McMaster, L. & Bruner, W. M. (1935). J. Am. Chem. Soc. 57, 1997-1998.  [CrossRef]
Navadiya, H. D., Undavia, N. K. & Patwa, B. S. (2008). Int. J. Chem. Sci. 6, 2224-2232.  [ChemPort]
Ravikrishnan, A., Sudhakara, P. & Kannan, P. (2012). J. Mater. Sci. 45, 435-442.  [Web of Science] [CrossRef]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Vögtle, F. & Weber, E. (1979). Angew. Chem. Int. Ed. 18, 753-776.
Waibel, M., De Angelis, M., Stossi, F., Kieser, K. J., Carlson, K. E., Katzenellenbogen, B. S. & Katzenellenbogen, J. A. (2009). Eur. J. Med. Chem. 44, 3412-3424.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Weber, E. & Vögtle, F. (1975). Tetrahedron Lett. pp. 2415-2418.  [CrossRef]
Yoneda, S., Ohfuchi, S., Hashimoto, A. & Kitamura, C. (2002). Kenkyu Hokuku Himeji Kogyo Daigaku, 54, 60-67.
Yuan, G.-Z., Rong, L.-L., Huo, Y.-P., Nie, X.-L. & Fang, X.-M. (2012). Inorg. Chem. Commun. 23, 90-94.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Zeng, H.-P., Wang, T.-T., Xu, D.-F., Cai, Y.-P. & Chen, D.-F. (2007). J. Appl. Cryst. 40, 471-475.  [Web of Science] [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Zhu, Y.-C., Lu, H.-X., He, D. H. & Yang, Z.-R. (2013). J. Photochem. Photobiol. B, 125, 8-12.  [Web of Science] [CrossRef] [ChemPort] [PubMed]


Acta Cryst (2013). E69, o1651-o1652   [ doi:10.1107/S1600536813027815 ]

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