Crystal structure of (E)-diethyl 2-[(1-phenyl­sulfonyl-1H-indol-3-yl)methyl­idene]succinate

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

doi:10.1107/S2056989015023075

. 2015 Dec 9;71(Pt 12):o1029–o1030. doi: 10.1107/S2056989015023075

Crystal structure of (E)-diethyl 2-[(1-phenylsulfonyl-1H-indol-3-yl)methylidene]succinate

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

PMCID: PMC4719962 PMID: 26870481

Abstract

In the title compound, C₂₃H₂₃NO₆S, the phenyl ring is perpendicular [dihedral angle = 89.34 (9)°] to the indole ring system. In the molecule, the ethoxy groups are each disordered over two sets of sites with occupancy ratios of 0.671 (6):0.329 (6) and 0.75 (3):0.25 (3). The molecular conformation is consolidated by a weak C—H⋯O interaction, which generates an S(6) graph–set motif. The packing of the molecules in the crystal structure features weak C—H⋯π interactions.

Keywords: crystal structure, indole derivative, hydrogen bonding

Related literature

For the biological activity of indole derivatives, see: Andreani et al. (2001 ▸); Kolocouris et al. (1994 ▸). For the structures of closely related compounds, see: Chakkaravarthi et al. (2007 ▸, 2008 ▸).

Experimental

Crystal data

C₂₃H₂₃NO₆S
M _r = 441.48
Monoclinic,
a = 8.3458 (8) Å
b = 24.657 (2) Å
c = 10.9448 (9) Å
β = 91.121 (3)°
V = 2251.8 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.18 mm⁻¹
T = 295 K
0.30 × 0.24 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▸) T _min = 0.947, T _max = 0.965
31225 measured reflections
4631 independent reflections
2889 reflections with I > 2σ(I)
R _int = 0.045

Refinement

R[F ² > 2σ(F ²)] = 0.049
wR(F ²) = 0.139
S = 1.03
4631 reflections
322 parameters
5 restraints
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.35 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) global, I. DOI: 10.1107/S2056989015023075/rk2433sup1.cif

e-71-o1029-sup1.cif^{(34.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015023075/rk2433Isup2.hkl

e-71-o1029-Isup2.hkl^{(222.3KB, hkl)}

Click here for additional data file.^{(8.1KB, cml)}

Supporting information file. DOI: 10.1107/S2056989015023075/rk2433Isup3.cml

Click here for additional data file.^{(1.5MB, tif)}

. DOI: 10.1107/S2056989015023075/rk2433fig1.tif

The molecular structure of title compound, with atom labels. Displacement ellipsoids are drawn at 30% probability level. The H atoms are presented as a small spheres of arbitrary radius. The minor components of the disordered ethyl groups are omitted for clarity.

CCDC reference: 1439879

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

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

Cg2 is the centroid of C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O1	0.93	2.44	3.012 (4)	120
C12—H12⋯Cg2ⁱ	0.93	2.80	3.561 (4)	140

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Symmetry code: (i) Inline graphic .

Acknowledgments

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

supplementary crystallographic information

S1. Structural commentary

Indole derivatives exhibit antitumour (Andreani et al., 2001) and antiviral (Kolocouris et al., 1994) activities. The molecular structure of the title compound is illustrated in (Fig. 1). The geometric parameters of the title molecule agree well with the reported similar structures (Chakkaravarthi et al. 2007, 2008).

The phenyl ring (C1–C6) is perpendicular [dihedral angle of 89.34 (9)°] to indole ring (N1/C7–C14) system in the molecule. In the terminal site, the ethoxy group is disordered over two positions with site occupancies of 0.671 (6) for major component (O4/C19/C20) and 0.329 (6) for minor component (O4A/C19A/C20A). The other ethoxy group is also disordered over two positions with site occupancies of 0.75 (3) for major component (O6/C23/C24) and 0.25 (3) for minor component (O6A/C23A/C24A). The torsion angles O1—S1—N1—C14 and O2—S1—N1—C7 [39.9 (2)° and −32.8 (2)°, respectively] indicate the syn–conformation of the sulfonyl moiety. The molecular structure is stabilized by weak non–classical C—H···O hydrogen bond which generates S(6) graph–set (Table 1 & Fig. 1) motif. The crystal structure is influenced by weak C—H···π (Table 1) interactions in a three–dimensional network.

S2. Synthesis and crystallization

To a solution of 1–(phenylsulfonyl)–1H–indole–3–carboxaldehyde (0.5 g, 1.84 mmol) and phosphorous ylide (C₂₆H₂₇O₄P) (0.96 g, 2.21 mmol) [prepared from (carbethoxymethylene)triphenylphosphorane and ethyl bromoacetate] in dry toluene (10 ml) was refluxed for 24 h. Then the solvent was removed under reduced pressure. The solid obtained was recrystallized from methanol (3 ml) to afford the title compound as a colourless crystal suitable for X–Ray diffraction analysis.

S3. Refinement

The H atoms were positioned geometrically and refined using riding model, with C—H = 0.93 Å and U_iso(H) = 1.2U_eq(C) for aromatic H, C—H = 0.97 Å and U_iso(H) = 1.2U_eq(C) for methylene H and C—H = 0.96 Å and U_iso(H) = 1.5U_eq(C) for methyl H.

The reflections [1 2 2], [0 2 0] and [0 1 1] were omitted during refinement which were owing poor agreement. The bond distances (C19—C20), (C19A—C20A), (C22—C23) and (C22A—C23A) were restraint to 1.54 (1) Å. The anisotropic displacement parameters of terminal site disordered atoms were equalized for the major and minor components with EADP instruction for C20 & C20A and C19 & C19A. The anisotropic displacement parameters in the direction of S1 and O2 were restraint within 0.001 using DELU instruction in SHELXL refinement.