1-(4-{2-[(E)-3-(4-Chloro­phen­yl)-3-oxo­prop-1-en-1-yl]phen­oxy}but­yl)-1H-indole-3-carbaldehyde

S Paramasivam; Santhanagopalan Purushothaman; P R Seshadri; Raghavachary Raghunathan

doi:10.1107/S1600536813002456

. 2013 Jan 31;69(Pt 2):o314–o315. doi: 10.1107/S1600536813002456

1-(4-{2-[(E)-3-(4-Chlorophenyl)-3-oxoprop-1-en-1-yl]phenoxy}butyl)-1H-indole-3-carbaldehyde

S Paramasivam ^a, Santhanagopalan Purushothaman ^b, P R Seshadri ^a,^*, Raghavachary Raghunathan ^b

PMCID: PMC3569833 PMID: 23424579

Abstract

In the title compound, C₂₈H₂₄ClNO₃, the dihedral angles between the central benzene ring and the indole ring system and the chlorobenzene ring are 70.81 (5) and 78.62 (5)°, respectively. The molecular structure is stabilized by a weak intramolecular C—H⋯O interaction. In the crystal, pairs of C—H⋯O hydrogen bonds link the molecules into inversion dimers with an R ₂ ²(14) motif.

Related literature

For the biological activity of indole derivatives, see: Olgen & Coban (2003 ▶); Ho et al. (1986 ▶); Joshi & Chand (1982 ▶); Rodriguez et al. (1985 ▶); Okabe & Adachi (1998 ▶); Merck (1973 ▶). For N-atom hybridization, see: Beddoes et al. (1986 ▶). For a related structure, see: Paramasivam et al. (2012 ▶). For graph-set notation see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₂₈H₂₄ClNO₃
M _r = 457.93
Monoclinic,
a = 8.7126 (3) Å
b = 19.1311 (6) Å
c = 13.9338 (4) Å
β = 93.198 (2)°
V = 2318.89 (13) Å³
Z = 4
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 298 K
0.20 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEXII area-detector diffractometer
22253 measured reflections
5782 independent reflections
4060 reflections with I > 2σ(I)
R _int = 0.026

Refinement

R[F ² > 2σ(F ²)] = 0.049
wR(F ²) = 0.145
S = 1.03
5782 reflections
298 parameters
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.46 e Å⁻³

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windowa (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97, PLATON and publCIF (Westrip, 2010 ▶).

Supplementary Material

Click here for additional data file.^{(31.6KB, cif)}

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813002456/kp2444sup1.cif

e-69-0o314-sup1.cif^{(31.6KB, cif)}

Click here for additional data file.^{(277.4KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813002456/kp2444Isup2.hkl

e-69-0o314-Isup2.hkl^{(277.4KB, hkl)}

Click here for additional data file.^{(8.6KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813002456/kp2444Isup3.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⋯O2	0.93	2.26	2.850 (2)	121
C20—H20⋯O1ⁱ	0.93	2.52	3.374 (2)	152

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors acknowledge the Technology Business Incubator (TBI), CAS in Crystallography, University of Madras, Chennai 600 025, India, for the data collection.

supplementary crystallographic information

Comment

Indole derivatives exhibit antioxidant (Olgen & Coban, 2003), central nervous system depressant and muscle relaxant properties (Ho et al., 1986), antifungicidal (Joshi & Chand, 1982), antimicrobial, antiinflammatory and antiimplantation (Rodriguez et al., 1985), antibacterial (Okabe & Adachi, 1998) and antihypertensive (Merck, 1973) activities. Against this background, the title compound was chosen for X-ray structure analysis (Fig. 1).

The indole ring is planar and it makes the dihedral angle with the chlorophenyl ring of 78.62 (05)°.

The sum of the bond angles around N1 [359.94 (44)°] indicates sp² hybridization (Beddoes et al., 1986). The geometric parameters of the title molecule (Fig. 1) agree well with reported similar structure (Paramasivam et al., 2012).

The molecular structure is stabilised by a weak C—H···O intramolecular interaction and the crystal packing reveals a weak C—H···O hydrogen bonds (Fig. 2). In the crystal structure, the molecules at (x, y, z) and (- x, - y + 1, - z + 2) are linked by C20—H20···O1 hydrogen bond, generating a centrosymmetric dimeric ring motif R₂²(14) (Bernstein et al., 1995).

Experimental

2 g (13.7 mmol) of 1H-indole-3-carbaldehyde in 25 mL dry DMF and anhydrous potassium carbonate (2 g, 13.7 mmol) were stirred for 15 min at room temperature followed by addition of 5.4 g (13.7 mmol) of (E)-3-(2-(4-bromobutoxy)phenyl)-1-(4-chlorophenyl)prop-2-en-1-one in 30 mL dry DMF with continued stirring for about 3 h at room temperature. After the completion of the reaction as evidenced from TLC, the solvent was filtered into crushed ice and extracted with chloroform. The organic extract was dried over Na2SO4 and concentrated under reduced pressure. Chromatography of the residue eluting with hexane/ethyl acetate mixture (8:2) gave pure (E)-1-(4-(2-(3-(4-chlorophenyl)-3-oxoprop-1-enyl)phenoxy)butyl)-1H-indole-3-carbaldehyde in good yield.