(E)-3-[4-(Dimethyl­amino)­phen­yl]-1-(2-methyl-4-phenyl­quinolin-3-yl)prop-2-en-1-one 0.7-hydrate

Loh, W.-S.; Fun, H.-K.; Sarveswari, S.; Vijayakumar, V.; Prasath, R.

doi:10.1107/S1600536811019088

Volume 67
Part 6
Pages o1521-o1522
June 2011

Received 5 May 2011
Accepted 19 May 2011
Online 25 May 2011

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
Disorder in solvent or counterion
R = 0.051
wR = 0.158
Data-to-parameter ratio = 30.6
Details

(E)-3-[4-(Dimethylamino)phenyl]-1-(2-methyl-4-phenylquinolin-3-yl)prop-2-en-1-one 0.7-hydrate

Wan-Sin Loh,^a ⁺ Hoong-Kun Fun,^a ^*⁺⁺ S. Sarveswari,^b V. Vijayakumar ^b and R. Prasath ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bOrganic Chemistry Division, School of Advanced Sciences, VIT University, Vellore 632 014, India
Correspondence e-mail: hkfun@usm.my

In the title compound, C₂₇H₂₄N₂O·0.7H₂O, the quinoline ring system is approximately planar, with a maximum deviation of 0.011 (1) Å, and forms dihedral angles of 74.70 (4) and 80.14 (4)° with the phenyl and benzene rings, respectively. In the crystal, the molecules are linked to the water molecules via intermolecular O-HN hydrogen bonds and further stabilized by C-H [pi] interactions involving the centroid of the benzene ring of the quinoline group. This benzene ring is observed to form a [pi] - [pi] interaction with an adjacent pyridine ring [centroid-centroid distance = 3.7120 (6) Å].

Related literature

For background to chalcone derivatives, see: Sarveswari & Vijayakumar (2011); Sarveswari et al. (2010); Loh et al. (2010b); Shahani et al. (2010). For related structures, see: Fun et al. (2009); Loh et al. (2010a). For bond-length data, see: Allen et al. (1987). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental

Crystal data

C₂₇H₂₄N₂O·0.7H₂O
M_r = 405.09
Triclinic, $[P \overline 1]$
a = 9.2653 (2) Å
b = 10.6076 (2) Å
c = 12.2347 (2) Å
= 66.409 (1)°
= 87.758 (1)°
= 80.308 (1)°
V = 1085.70 (4) Å³
Z = 2
Mo K radiation
= 0.08 mm^-1
T = 100 K
0.47 × 0.31 × 0.22 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009) T_min = 0.964, T_max = 0.983
28425 measured reflections
8843 independent reflections
6883 reflections with I > 2(I)
R_int = 0.024

Refinement

R[F² > 2(F²)] = 0.051
wR(F²) = 0.158
S = 1.05
8843 reflections
289 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.45 e Å^-3
_min = -0.25 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1-C6 ring.

D-HA	D-H	HA	DA	D-HA
O1W-H1W1N1ⁱ	0.85 (2)	2.01 (2)	2.8650 (17)	176 (2)
C14-H14ACg1ⁱⁱ	0.95	2.81	3.6395 (14)	147
Symmetry codes: (i) x, y+1, z; (ii) -x+1, -y+1, -z.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ2594 ).

Acknowledgements

HKF and WSL thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). WSL also thanks the Malaysian Government and USM for the award of a Research Fellowship. VV is grateful to the DST-India for funding through the Young Scientist Scheme (Fast Track Proposal).

References

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.
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.
Fun, H.-K., Loh, W.-S., Sarveswari, S., Vijayakumar, V. & Reddy, B. P. (2009). Acta Cryst. E65, o2688-o2689.
Loh, W.-S., Fun, H.-K., Sarveswari, S., Vijayakumar, V. & Reddy, B. P. (2010a). Acta Cryst. E66, o91-o92.
Loh, W.-S., Fun, H.-K., Sarveswari, S., Vijayakumar, V. & Reddy, B. P. (2010b). Acta Cryst. E66, o353-o354.
Sarveswari, S. & Vijayakumar, V. (2011). Arab. J. Chem. doi:10.1016/j.arabjc.2011.01.032.
Sarveswari, S., Vijayakumar, V., Prasath, R., Narasimhamurthy, T. & Tiekink, E. R. T. (2010). Acta Cryst. E66, o3284.
Shahani, T., Fun, H.-K., Sarveswari, S., Vijayakumar, V. & Ragavan, R. V. (2010). Acta Cryst. E66, o374.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds