4-(4-Bromo­phen­yl)-2-oxo-1,2,5,6-tetra­hydro­benzo[h]quinoline-3-carbonitrile

Abdullah M Asiri; Hassan M Faidallah; Abdulrahman O Al-Youbi; Khalid A Alamry; Seik Weng Ng

doi:10.1107/S1600536811033885

. 2011 Aug 27;67(Pt 9):o2469. doi: 10.1107/S1600536811033885

4-(4-Bromophenyl)-2-oxo-1,2,5,6-tetrahydrobenzo[h]quinoline-3-carbonitrile

Abdullah M Asiri ^a, Hassan M Faidallah ^a, Abdulrahman O Al-Youbi ^a, Khalid A Alamry ^a, Seik Weng Ng ^b,^a,^*

PMCID: PMC3200630 PMID: 22064644

Abstract

In the molecule of the title compound, C₂₀H₁₃BrN₂O, the tetrahydrobenzo[h]quinoline fused-ring system is buckled owing to the ethylene –CH₂CH₂– fragment, the benzene ring and the pyridine ring being twisted by 17.7 (1)°. The 4-substituted aromatic ring is bent away from the pyridine ring by 82.3 (1)° in order to avoid crowding the cyanide substituent. Two molecules are linked by a pair of N—H⋯O hydrogen bonds to form a centrosymmetric dimer.

Related literature

For background to the anticancer properties of this class of compounds, see: Rostom et al. (2011 ▶).

Experimental

Crystal data

C₂₀H₁₃BrN₂O
M _r = 377.23
Monoclinic,
a = 22.6906 (5) Å
b = 8.5060 (2) Å
c = 17.6112 (5) Å
β = 106.498 (3)°
V = 3259.13 (14) Å³
Z = 8
Cu Kα radiation
μ = 3.50 mm⁻¹
T = 100 K
0.30 × 0.25 × 0.20 mm

Data collection

Agilent SuperNova Dual diffractometer with Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T _min = 0.420, T _max = 0.541
6063 measured reflections
3244 independent reflections
3132 reflections with I > 2σ(I)
R _int = 0.022

Refinement

R[F ² > 2σ(F ²)] = 0.032
wR(F ²) = 0.094
S = 1.06
3244 reflections
221 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.56 e Å⁻³
Δρ_min = −0.57 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811033885/xu5291sup1.cif

e-67-o2469-sup1.cif^{(18.4KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811033885/xu5291Isup2.hkl

e-67-o2469-Isup2.hkl^{(159.2KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811033885/xu5291Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.86 (3)	1.96 (3)	2.807 (2)	172 (3)

Open in a new tab

Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank King Abdulaziz University and the University of Malaya for supporting this study.

supplementary crystallographic information

Comment

The compound (Scheme I) belongs to a series of cyano-pyridinones that have been evaluated for their anticancer properties (Rostom et al., 2011). The tetrahydrobenzo[h]quinoline fused-ring system is buckled owing to the ethylene –CH₂CH₂– fragment, the benzene ring and the pyridine ring being twisted by 17.7 (1)°. The 4-subsituted aromatic ring is bent away from the pyridine ring by 83.2 (1) ° in order to avoid crowding the cyanide substituent (Fig. 1). Two molecules are linked by an N—H···O hydrogen bonds to form a centrosymmetric dimer (Table 1).

Experimental

A mixture of p-bromobenzaldehyde (1.85 g, 10 mmol), 1-tetralone (1.46 g, 10 mmol), ethyl cyanoacetate (1.1 g, 10 mmol) and ammonium acetate (6.2 g, 80 mmol) in absolute ethanol (50 ml) was refluxed for 6 h. The reaction mixture was allowed to cool, and the orange precipitate that formed was filtered, washed with water, dried and recrystallized from ethanol; m.p. >630 K.