(E)-1-[2-(4-Fluoro-2-nitro­styr­yl)-1-phenyl­sulfonyl-1H-indol-3-yl]propan-1-one

M Umadevi; V Saravanan; R Yamuna; A K Mohanakrishnan; G Chakkaravarthi

doi:10.1107/S1600536813030961

. 2013 Nov 16;69(Pt 12):o1780. doi: 10.1107/S1600536813030961

(E)-1-[2-(4-Fluoro-2-nitrostyryl)-1-phenylsulfonyl-1H-indol-3-yl]propan-1-one

M Umadevi ^a, V Saravanan ^b, R Yamuna ^c,^*, A K Mohanakrishnan ^b, G Chakkaravarthi ^d,^*

PMCID: PMC3885049 PMID: 24454225

Abstract

In the title compound, C₂₅H₁₉FN₂O₅S, the substituted phenyl ring makes a dihedral angle of 12.26 (9)° with the indole ring system. The nitro group is twisted at an angle of 26.92 (8)° out of the plane of the ring to which it is attached. The molecular structure is stabilized by weak C—H⋯O hydrogen bonds. In the crystal, weak C—H⋯O, C—H⋯F and π–π [centroid–centroid distance = 3.6645 (11) Å] interactions link the molecules, forming a three-dimensional network.

Related literature

For the biological activity of indole derivatives, see: Pomarnacka & Kozlarska-Kedra (2003 ▶); Srivastava et al. (2011 ▶). For related structures, see: Chakkaravarthi et al. (2008 ▶, 2010 ▶). For details of the configuration at the S atom, see: Bassindale (1984 ▶). For details of N-atom hybridization, see: Beddoes et al. (1986 ▶). graphic file with name e-69-o1780-scheme1.jpg

Experimental

Crystal data

C₂₅H₁₉FN₂O₅S
M _r = 478.48
Triclinic,
a = 8.2615 (3) Å
b = 10.7624 (5) Å
c = 13.2432 (6) Å
α = 68.606 (2)°
β = 80.554 (3)°
γ = 81.012 (2)°
V = 1075.53 (8) Å³
Z = 2
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 295 K
0.30 × 0.24 × 0.20 mm

Data collection

Bruker APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.942, T _max = 0.961
27388 measured reflections
8185 independent reflections
5506 reflections with I > 2σ(I)
R _int = 0.028

Refinement

R[F ² > 2σ(F ²)] = 0.055
wR(F ²) = 0.176
S = 1.03
8185 reflections
308 parameters
H-atom parameters constrained
Δρ_max = 0.96 e Å⁻³
Δρ_min = −0.61 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); 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) I, global. DOI: 10.1107/S1600536813030961/bt6945sup1.cif

e-69-o1780-sup1.cif^{(31.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813030961/bt6945Isup2.hkl

e-69-o1780-Isup2.hkl^{(392.3KB, hkl)}

Click here for additional data file.^{(8.3KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813030961/bt6945Isup3.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
C8—H8⋯O1	0.93	2.33	2.913 (3)	120
C11—H11⋯O3	0.93	2.40	2.905 (3)	114
C16—H16A⋯F1ⁱ	0.97	2.54	3.192 (2)	124
C22—H22⋯O4ⁱⁱ	0.93	2.52	3.438 (2)	170

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

The authors wish to acknowledge the SAIF, IIT, Madras, for the data collection.

supplementary crystallographic information

1. Comment

Indole derivatives are known to exhibit antimicrobial, antibiotic, analgesic, anticancer and anti-HIV (Pomarnacka & Kozlarska-Kedra, 2003; Srivastava et al., 2011) activities. In continuation of our studies on indole derivatives, we determined the crystal structure of the title compound (I). The geometric parameters of (I) (Fig. 1) are agree well with the reported structures (Chakkaravarthi et al., 2008; 2010).

Due to Thorpe-Ignold effect (Bassindale, 1984), bond angles around atom S1 show significant deviation from ideal tetrahedral value, with significant deviations in angles O1—S1—O2 [120.42 (8)°] and N1—S1—C1 [104.66 (7)°]. The phenyl ring (C1—C6) makes the dihedral angle of 85.05 (8)° with the indole ring system. The phenyl ring (C1—C6) and the benzene ring (C20—C25) are inclined at an angle of 12.26 (9)°. The nitro group is twisted at an angle of 26.92 (8)° with the attached benzene ring (C20—C25). The sum of the bond angles around N1 (358.26°) indicates the sp² hybridization of N1 atom (Beddoes et al., 1986).

The molecular structure is stabilized by weak intramolecular C—H···O hydrogen bonds (Table 1). The crystal structure exhibit weak intermolecular C—H···O, C—H···F (Table 1 & Fig. 2) and π···π [Cg4···Cg4ⁱ = 3.6645 (11) Å; (i) 1 - x, -1 - y, 2 - z; Cg4 is the centroid of the ring (C20—C25)] interactions.

2. Experimental

A solution of 1-(2-(bromomethyl)-1-(phenylsulfonyl)-1H-indol-3-yl) propan-1-one (5 g, 12.31 mmol) and triphenylphosphine (3.5 g, 13.54 mmol) in dry THF (100 ml) was refluxed for 6 h. After consumption of the starting material, the solvent was removed under vacuo and the solid was washed with diethyl ether to give the phosphonium salt. Then, the mixture of phosphonium salt (8 g, 11.97 mmol), 4-fluoro-2-nitrobenzaldehyde (2.24 g, 13.17 mmol) and K₂CO₃ (3.30 g, 23.95 mmol) in DCM (70 ml) was stirred at room temperature for 22 h. After completion of the reaction (monitored by TLC), it was diluted using DCM (30 ml), washed with water (2 x 100 ml) and dried (Na₂SO₄). Removal of solvent in vacuo followed by trituration of the crude product with MeOH (20 ml) afforded the title compound suitable for X-ray diffraction quality.