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Volume 69 
Part 8 
Page o1319  
August 2013  

Received 22 July 2013
Accepted 22 July 2013
Online 27 July 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.003 Å
R = 0.058
wR = 0.167
Data-to-parameter ratio = 15.6
Details
Open access

(2E)-3-(6-Chloro-2-methoxyquinolin-3-yl)-1-(2-methyl-4-phenylquinolin-3-yl)prop-2-en-1-one acetone monosolvate

aDepartment of Chemistry, BITS, Pilani - K. K. Birla Goa Campus, Goa 403 726, India,bCentre for Organic and Medicinal Chemistry, VIT University, Vellore 632 014, India,cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and dChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
Correspondence e-mail: edward.tiekink@gmail.com

In the title solvate, C29H21ClN2O2·C3H6O, a prop-2-en-1-one bridge links two quinolinyl residues; the latter are almost perpendicular [dihedral angle = 78.27 (6)°]. The dihedral angle between the quinonyl ring system and its pendant phenyl group is 59.78 (8)°. A small twist in the bridging prop-2-en-1-one group is noted [O=C-C=C torsion angle = -10.6 (3)°]. In the crystal, a three-dimensional architecture arises as a result of C-H...O and [pi]-[pi] stacking [centroid-centroid distances = 3.5504 (12)-3.6623 (12) Å].

Related literature

For background details and the biological applications of quinolinyl derivatives, see: Joshi et al. (2011[Joshi, R. S., Mandhane, P. G., Khan, W. & Gill, C. H. (2011). J. Heterocycl. Chem. 48, 872-876.]); Prasath et al. (2013a[Prasath, R., Bhavana, P., Ng, S. W. & Tiekink, E. R. T. (2013a). J. Organomet. Chem. 726, 62-70.]). For a related structure, see: Prasath et al. (2013b[Prasath, R., Sarveswari, S., Ng, S. W. & Tiekink, E. R. T. (2013b). Acta Cryst. E69, o1274.]).

[Scheme 1]

Experimental

Crystal data
  • C29H21ClN2O2·C3H6O

  • Mr = 523.01

  • Monoclinic, P 21 /c

  • a = 17.1714 (3) Å

  • b = 10.7099 (2) Å

  • c = 14.5248 (2) Å

  • [beta] = 100.021 (2)°

  • V = 2630.42 (8) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 1.58 mm-1

  • T = 100 K

  • 0.30 × 0.25 × 0.20 mm

Data collection
  • Agilent SuperNova Dual diffractometer with an Atlas detector

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013[Agilent (2013). CrysAlis PRO. Agilent Technologies Inc., Santa Clara, CA, USA.]) Tmin = 0.665, Tmax = 1.000

  • 11367 measured reflections

  • 5408 independent reflections

  • 4574 reflections with I > 2[sigma](I)

  • Rint = 0.032

Refinement
  • R[F2 > 2[sigma](F2)] = 0.058

  • wR(F2) = 0.167

  • S = 1.03

  • 5408 reflections

  • 346 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 1.47 e Å-3

  • [Delta][rho]min = -0.46 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C26-H26...O2i 0.95 2.47 3.319 (3) 149
C30-H30A...O1i 0.98 2.52 3.373 (4) 146
C28-H28...O3 0.95 2.57 3.467 (3) 158
Symmetry code: (i) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: CrysAlis PRO (Agilent, 2013[Agilent (2013). CrysAlis PRO. Agilent Technologies Inc., Santa Clara, CA, USA.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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.]) and DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: 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: HG5334 ).


Acknowledgements

RP gratefully acknowledges the Council of Scientific and Industrial Research (CSIR), India, for a Senior Research Fellowship (09/919/(0014)/2012 EMR-I). We also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR-MOHE/SC/03).

References

Agilent (2013). CrysAlis PRO. Agilent Technologies Inc., Santa Clara, CA, USA.
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Joshi, R. S., Mandhane, P. G., Khan, W. & Gill, C. H. (2011). J. Heterocycl. Chem. 48, 872-876.  [CrossRef] [ChemPort]
Prasath, R., Bhavana, P., Ng, S. W. & Tiekink, E. R. T. (2013a). J. Organomet. Chem. 726, 62-70.  [CSD] [CrossRef] [ChemPort]
Prasath, R., Sarveswari, S., Ng, S. W. & Tiekink, E. R. T. (2013b). Acta Cryst. E69, o1274.  [CrossRef] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1319  [ doi:10.1107/S1600536813020217 ]

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