Crystal structure of 1-{4-hydroxy-3-[(pyrrolidin-1-yl)methyl]phenyl}-3-phenylprop-2-en-1-one

In the title compound, the pyrrolidine ring adopts an envelope conformation, which may be correlated with the intramolecular O—H⋯N hydrogen bond.


Chemical context
Mannich bases are a group of compounds having various biological activities such as cytotoxic (Bilginer et al., 2013), anti-inflammatory (Sahin et al., 2010) and anticonvulsant (Gul et al., 2004) activities. ,-Unsaturated ketones present in the chemical structure of Mannich bases themselves or those produced from them by deamination processes are responsible for their cytotoxicity.

Supramolecular features
The only directional interaction present in the crystal of (I) is a very weak C-HÁ Á Á bond (Table 1).

Semi-empirical quantum-mechanical calculations
A theoretical calculation was carried out using the semiempirical quantum-mechanical CNDO/2 (Complete Neglect of Differential Overlap) method (Pople & Beveridge, 1970). The spatial view of the single molecule, with atomic labels, calculated as a closed-shell in a vacuum is shown in Fig. 3. The charges at atoms O1, O2 and N1 are À0.337, À0.271 and À0.159 e À , respectively. The calculated dipole moment is 2.760 Debye.

Biological activity
Compound (I) was tested against human hepatoma (Huh7) and breast cancer cell (T47D) lines in terms of its cytotoxic activities, and showed activities against both cell lines used, especially against the T47D cell line. The compound studied here may serve as a model compound for designing new anticancer compounds for further studies (Yerdelen, 2009).
Cg3 is the centroid of the C10-C15 ring.

Figure 2
The molecular packing and hydrogen bonding viewed down the a axis.

Figure 3
The conformation of the title compound, calculated using the CNDO method.

Figure 1
View of the molecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level.

Special details
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles Refinement. Refinement on F 2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The observed criterion of F 2 > 2sigma(F 2 ) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.