5-Meth­oxy-3-[(5-meth­oxy-1H-indol-3-yl)(phen­yl)meth­yl]-1H-indole

P Narayanan; K Sethusankar; K Ramachandiran; P T Perumal

doi:10.1107/S1600536811045491

. 2011 Nov 5;67(Pt 12):o3196. doi: 10.1107/S1600536811045491

5-Methoxy-3-[(5-methoxy-1H-indol-3-yl)(phenyl)methyl]-1H-indole

P Narayanan ^a, K Sethusankar ^a,^*, K Ramachandiran ^b, P T Perumal ^b

PMCID: PMC3238863 PMID: 22199716

Abstract

In the title compound, C₂₅H₂₂N₂O₂, the indole rings are individually almost planar [with maximum deviations of 0.0116 (19) and 0.0113 (18) Å] and are almost orthogonal to each other, making a dihedral angle of 84.49 (6)°. The benzene ring is inclined at 72.83 (9) and 80.85 (9)° with respect to the indole rings. In the crystal, molecules are linked by N—H⋯O interactions into chains running parallel to the c axis. The crystal structure is further stabilized by C—H⋯π interactions.

Related literature

For the biological activity and uses of indole derivatives, see: Bell et al. (1994 ▶); Ge et al. (1996 ▶). For related structures, see: Zhang et al. (2006 ▶, 2007 ▶).

Experimental

Crystal data

C₂₅H₂₂N₂O₂
M _r = 382.45
Monoclinic,
a = 9.1545 (4) Å
b = 10.5954 (6) Å
c = 21.1668 (13) Å
β = 93.679 (2)°
V = 2048.86 (19) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.25 × 0.20 × 0.15 mm

Data collection

Bruker APEXII KappaCCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T _min = 0.981, T _max = 0.988
16790 measured reflections
3087 independent reflections
2317 reflections with I > 2σ(I)
R _int = 0.034
θ_max = 23.7°

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.119
S = 1.03
3087 reflections
264 parameters
H-atom parameters constrained
Δρ_max = 0.12 e Å⁻³
Δρ_min = −0.18 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 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811045491/pv2461sup1.cif

e-67-o3196-sup1.cif^{(22.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811045491/pv2461Isup2.hkl

e-67-o3196-Isup2.hkl^{(148.4KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811045491/pv2461Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

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

Cg2, Cg3, Cg4 and Cg5 are the centroids of the N2/C17–C20, C1–C6, C10–C15 and C19–C24 rings, respectively

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2ⁱ	0.86	2.09	2.904 (2)	158
C25—H25B⋯Cg2ⁱⁱ	0.96	2.95	3.515 (3)	119
C16—H16C⋯Cg3ⁱⁱⁱ	0.96	2.90	3.508 (3)	122
N2—H2A⋯Cg4^iv	0.86	2.49	3.3149 (19)	160
C3—H3⋯Cg5^v	0.93	2.60	3.470 (2)	157

Open in a new tab

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

Acknowledgments

PN and KS thank Dr Babu Varghese, Senior Scientific Officer, SAIF, IIT, Chennai, India, for the X-ray intensity data collection and Dr V. Murugan, Head of the Department of Physics, for providing facilities in the department to carry out this work.

supplementary crystallographic information

Comment

The synthesis of bis-indolylalkanes (BIAs) has been of considerable interest because of their occurance in various natural products posessing biological activities and usefulness in drug design (Bell, et al. 1994). These compounds also inhibit the proliferation of both estrogen dependent and independent cultured breast tumor cells (Ge, et al. 1996). In this paper, we present the synthesis and crystal structure of the title bis-indolylalkane derivative.

The title compound (Fig. 1) comprises a benzene ring and two methoxy indole rings connected through a carbon atom C7. The bicyclic indole rings, are individually planar with maximum deviations of 0.0116 (19)Å for C10 atom, in ring A (N1/C8–C15) and -0.0113 (18)Å for N2 atom, in ring B (N2/C17–C24). The indole rings are almost orthogonal to each other, with a dihedral angle of 84.49 (6)°. The deviations of methoxy group carbon atoms C16 and C25 from the rings A & B, are -0.118 (3)Å and -0.100 (3) Å, respectively.

The benzene ring (C1–C6) is inclined at 72.83 (9)° and 80.85 (9)°, with the indole rings A & B, respectively. The angles around atom C7 [C8–C7–C17 = 113.07 (14)°, C8–C7–C6 = 112.52 (14)° and C17–C7–C6 = 111.53 (15)°] deviate significantly from the ideal tetrahedral values which may be a result of steric interactions between benzene ring and the indole rings.

In the crystal packing, the molecules are linked by N—H···O intermolecular interactions into infinite chains running parallel to the c axis (Fig. 2). The crystal structure is further stabilized by C—H···Cg interactions where Cg2, Cg3, Cg4 and Cg5 are the centers of gravity of rings (N2/C17–C20), (C1–C6), (C10–C15) and (C19–C24), respectively (Table 1).

Experimental

To benzaldehyde (1 mmol) in CH₂Cl₂ (10 ml) was added KHSO₄ (30 mol%) and the mixture was stirred for 5 min. Methoxyindole (2 mmol) was added to the mixture and the stirring was continued following the progress of the reaction by TLC. After completion of the reaction, the reaction mixture was extracted with ethyl acetate (3 x 10 ml), dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure and the residue was column chromatographed over silica gel using EtOAc/Petroleum ether (1:19) as eluent to get the pure product, the title compound, which was re-crystallized by slow evaporation of its solution in ethyl acetate, resulting in single crystals, suitable for XRD studies.