2-(4-Methyl­phen­yl)-1-phenyl­sulfonyl-3-nitro-1,2-dihydro­quinoline

J Kanchanadevi; G Anbalagan; V Saravanan; A K Mohanakrishnan; V Manivannan

doi:10.1107/S1600536811030455

. 2011 Aug 2;67(Pt 9):o2225. doi: 10.1107/S1600536811030455

2-(4-Methylphenyl)-1-phenylsulfonyl-3-nitro-1,2-dihydroquinoline

J Kanchanadevi ^a, G Anbalagan ^b, V Saravanan ^c, A K Mohanakrishnan ^c, V Manivannan ^d,^*

PMCID: PMC3200724 PMID: 22058902

Abstract

In the title compound, C₂₂H₁₈N₂O₄S, the dihedral angle between the phenylsulfonyl ring and the methylphenyl ring is 67.78 (7)°. In the crystal, molecules are linked by weak intermolecular C—H⋯O interactions into a zigzag chain along the [101] direction.

Related literature

For the biological activity of quinoline derivatives, see: Franck et al. (2004 ▶); Zouhiri et al. (2005 ▶); Paul et al. (1969 ▶). For a related structure, see: Xu et al. (2011 ▶).

Experimental

Crystal data

C₂₂H₁₈N₂O₄S
M _r = 406.44
Monoclinic,
a = 9.7349 (5) Å
b = 17.0241 (9) Å
c = 12.1068 (6) Å
β = 90.240 (2)°
V = 2006.42 (18) Å³
Z = 4
Mo Kα radiation
μ = 0.19 mm⁻¹
T = 295 K
0.35 × 0.30 × 0.25 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.945, T _max = 0.955
26473 measured reflections
5485 independent reflections
3224 reflections with I > 2σ(I)
R _int = 0.028

Refinement

R[F ² > 2σ(F ²)] = 0.048
wR(F ²) = 0.151
S = 1.03
5485 reflections
263 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Data collection: APEX2 (Bruker, 2003 ▶); cell refinement: SAINT (Bruker, 2003 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) global. DOI: 10.1107/S1600536811030455/is2758sup1.cif

e-67-o2225-sup1.cif^{(20.4KB, cif)}

Supplementary material file. DOI: 10.1107/S1600536811030455/is2758globalsup2.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
C4—H4⋯O4ⁱ	0.93	2.60	3.418 (4)	148

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Symmetry code: (i) Inline graphic .

supplementary crystallographic information

Comment

The quinoline and its derivatives have received much scientific attention during recent years, because of their wide spectrum of pharmacological activities (Franck et al., 2004; Zouhiri et al., 2005). In addition, the nitroquinoline derivatives possess a potent mutagenic, carcinogenic and carcinostatic agent (Paul et al., 1969).

The geometric parameters of the title molecule (Fig. 1) agree well with a reported similar structure (Xu et al., 2011). The phenylsulfonly ring and the methylphenyl ring are oriented at an angle of 67.78 (7)°. The sum of bond angles around N1 [352.34 (13)°] and N2 [359.95 (2)°] indicates the sp² hybridization state of atoms N1 and N2 in the molecule. The crystal packing is controlled by a weak intermolecular C—H···O interaction.

Experimental

To a solution of N-(2-formylphenyl) benzenesulfonamide (0.50 g, 1.91 mmol) in dry benzene (20 ml), DABACO (0.10 g, 0.95 mmol) and 1-methyl-4-(2-nitrovinyl)benzene (0.41 g, 2.29 mmol) were added. The reaction mixture was stirred at reflux condition for 24 hrs under N₂ atmosphere. The reaction mass was quenched with ice water (50 ml), extracted with chloroform (3 × 10 ml) and dried (Na₂SO₄). The solvent was removed under reduced pressure. Then the column chromatographic purification of crude product afforded pure dihydro nitroquinoline 18 as pale yellow solid with a yield of 82% and a melting point of 451 K.