Abstract
The title com-pound, C14H10N2O, crystallizes in the monoclinic space group P21/c with four mol-ecules in the unit cell. All 17 non-H atoms of one mol-ecule lie essentially in one plane. In the unit cell, two pairs of mol-ecules are exactly coplanar, while the angle between these two orientations is close to perfectly perpendicular at 87.64 (6)°. In the crystal, mol-ecules adopt a 50:50 crisscross arrangement, which is held together by two nonclassical and two classical inter-molecular hydrogen bonds. The hydrogen-bonding network together with off-centre π-π stacking inter-actions between the pyridine and outermost benzene rings, stack the mol-ecules along the b-axis direction.
Highlights
The title compound, C14H10N2O, crystallizes in the monoclinic space group P21/c with four molecules in the unit cell
By UV radiation, (E)-5-styrylnicotinamide was transformed to its Z isomer as envisioned, but underwent photocyclization and successive oxidation, yielding two isomeric benzoquinoline derivatives; the identity of one of these was determined to be the benzo[h]quinoline derivative and its crystal structure is reported here
Benzo[h]quinoline-3-carboxamide consists of a nicotinamide unit being fused with a benzo[h]quinoline moiety, while the pyridine ring is shared between these two common structural building blocks (Fig. 1)
Summary
Quinoline and benzoquinoline scaffolds are common structural motifs in artificial, as well as natural products, and many of these compounds are of enormous value for pharmacotherapy. Their multifaceted biological efficacy is outstanding and ranges from cardiovascular (Ferlin et al, 2002; Abouzid et al, 2008) and anti-inflammatory effects (Kumar et al, 2009; Hussaini, 2016) to antimicrobial (El Shehry et al, 2018), as well as anticancer activity (Abdelsalam et al, 2019; Haiba et al, 2019; Jafari et al, 2019; Musiol, 2017; Marzaro et al, 2016). Symmetry codes: (i) Àx þ 1; y À 12; Àz þ 12; (ii) Àx þ 1; Ày À 1; Àz þ 1; (iii) x; Ày þ 12; z À 12
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