Crystal structure of 3-(2-nitro­phen­yl)-1-(1-phenyl­sulfonyl-1H-indol-3-yl)propan-1-one

M Umadevi; Potharaju Raju; R Yamuna; Arasambattu K Mohanakrishnan; G Chakkaravarthi

doi:10.1107/S2056989015020162

. 2015 Oct 31;71(Pt 11):o892–o893. doi: 10.1107/S2056989015020162

Crystal structure of 3-(2-nitrophenyl)-1-(1-phenylsulfonyl-1H-indol-3-yl)propan-1-one

M Umadevi ^a,^b, Potharaju Raju ^c, R Yamuna ^d,^*, Arasambattu K Mohanakrishnan ^c, G Chakkaravarthi ^e,^*

PMCID: PMC4645035 PMID: 26594584

Abstract

In the title compound, C₂₃H₁₈N₂O₅S, the phenyl and benzene rings subtend dihedral angles of 78.18 (10) and 30.18 (9)°, respectively, with the indole ring system (r.m.s. deviation = 0.022 Å). The crystal structure features weak C—H⋯O and C—H⋯π interactions, which link the molecules into a three-dimensional network.

Keywords: crystal structure, indole, hydrogen bonding, C—H⋯π interactions

Related literature

For the biological activity of indole derivatives, see: Andreev et al. (2015 ▸); Kolocouris et al. (1994 ▸). For related structures, see: Chakkaravarthi et al. (2007 ▸, 2008 ▸).

Experimental

Crystal data

C₂₃H₁₈N₂O₅S
M _r = 434.45
Monoclinic,
a = 9.0224 (7) Å
b = 15.4581 (10) Å
c = 15.1347 (10) Å
β = 106.349 (2)°
V = 2025.5 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 295 K
0.26 × 0.24 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▸) T _min = 0.950, T _max = 0.961
29555 measured reflections
6149 independent reflections
4060 reflections with I > 2σ(I)
R _int = 0.033

Refinement

R[F ² > 2σ(F ²)] = 0.058
wR(F ²) = 0.144
S = 1.09
6149 reflections
280 parameters
3 restraints
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.32 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 and PLATON.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015020162/hb7524sup1.cif

e-71-0o892-sup1.cif^{(29.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015020162/hb7524Isup2.hkl

e-71-0o892-Isup2.hkl^{(294.9KB, hkl)}

Click here for additional data file.^{(7.6KB, cml)}

Supporting information file. DOI: 10.1107/S2056989015020162/hb7524Isup3.cml

Click here for additional data file.^{(1.2MB, tif)}

. DOI: 10.1107/S2056989015020162/hb7524fig1.tif

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

Click here for additional data file.^{(1.7MB, tif)}

. DOI: 10.1107/S2056989015020162/hb7524fig2.tif

The crystal packing of the title compound, viewed along the a axis. The C—H⋯O hydrogen bonds are shown as dashed lines (see Table 1). H atoms not involved in these interactions have been omitted for clarity.

CCDC reference: 1433093

Additional supporting information: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (, ).

Cg3 is the centroid of the C7C12 ring.

DHA	DH	HA	D A	DHA
C9H9O2ⁱ	0.93	2.54	3.328(2)	143
C22H22O3ⁱⁱ	0.93	2.42	3.319(3)	163
C23H23O5ⁱⁱⁱ	0.93	2.36	3.247(3)	160
C16H16A Cg3^iv	0.97	2.73	3.565(2)	144

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

Acknowledgments

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

supplementary crystallographic information

S1. Structural commentary

Indole derivatives are known to exhibit anti-hepatitis C virus (Andreev et al., 2015) and antiviral activity (Kolocouris et al., 1994). We herein report the crystal structure of (I) (Fig. 1). The ORTEP diagram of the title compound (I) is shown in Fig. 1. The geometric parameters of (I) are comparable with similar structures (Chakkaravarthi et al. 2007, 2008).

The phenyl ring (C1—C6) and benzene ring (C18—C23) make the dihedral angles of 78.18 (10)° and 30.18 (9)°, respectively with the indole ring system. The phenyl (C1—C6) and benzene (C18—C23) rings are inclined at angle of 69.93 (12)°. In the crystal structure, the intermolecular weak C—H···O and C—H···π (Fig. 2 & Table 1) interactions form a three dimensional network.

S2. Synthesis and crystallization

To a solution of 1-(phenylsulfonyl)-1H-indole (0.5 g, 1.94 mmol) in dry DCM 3-(2-nitrophenyl)propanoyl chloride (0.62 g, 2.92 mmol) and SnCl₄ (0.76 g, 2.92 mmol) were added slowly at 273 K under nitrogen atmosphere and the resulting mixture was stirred at room temperature for 30 min after completion of starting material (monitored by TLC), the reaction mass was poured over ice water containing Conc. HCl (3 ml) and extracted with DCM (20 ml). The combined organic extracts were washed with water (30 ml), brine solution (10 ml) and dried Na₂SO₄. Removal of solvent followed by recrystallization of the crude product from methanol (3 ml) solution afforded the title compound as colourless blocks.

S3. Refinement

H atoms were positioned geometrically and refined using riding model, with C—H = 0.93 Å and U_iso(H) = 1.2Ueq(C) for C—H and C—H = 0.97 Å and U_iso(H) = 1.2Ueq(C) for CH₂. The reflection (0 1 1) is omitted during refinement which is owing poor agreement.