1-(2-Methyl­benz­yl)-1H-indole-3-carbaldehyde

Yang Wu; Wen Ren; Qiang Wang; Gu He

doi:10.1107/S1600536812010306

. 2012 Mar 24;68(Pt 4):o1151. doi: 10.1107/S1600536812010306

1-(2-Methylbenzyl)-1H-indole-3-carbaldehyde

Yang Wu ^a, Wen Ren ^b, Qiang Wang ^b, Gu He ^c,^*

PMCID: PMC3344094 PMID: 22606097

Abstract

In the title compound, C₁₇H₁₅NO, the benzene ring and the indole system are almost perpendicular, making a dihedral angle of 87.82 (6)°. The crystal packing is stabilized by C—H⋯O and π–π stacking interactions with centroid–centroid distances of 3.592 (4) Å between the pyrrole and the benzene rings in the indole systems of neighboring molecules.

Related literature

For general background to the chemistry and anti-inflammatory activity of carboxylic acid derivatives, see: Andreani et al. (1994 ▶).

Experimental

Crystal data

C₁₇H₁₅NO
M _r = 249.30
Monoclinic,
a = 10.5251 (3) Å
b = 15.4352 (5) Å
c = 8.2335 (2) Å
β = 99.214 (3)°
V = 1320.33 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.28 × 0.25 × 0.20 mm

Data collection

Agilent Xcalibur Eos diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T _min = 0.981, T _max = 1.000
5468 measured reflections
2699 independent reflections
1928 reflections with I > 2σ(I)
R _int = 0.016

Refinement

R[F ² > 2σ(F ²)] = 0.047
wR(F ²) = 0.117
S = 1.04
2699 reflections
173 parameters
H-atom parameters constrained
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov, 2009 ▶); software used to prepare material for publication: OLEX2.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812010306/bt5840sup1.cif

e-68-o1151-sup1.cif^{(21.4KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812010306/bt5840Isup2.hkl

e-68-o1151-Isup2.hkl^{(132.6KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812010306/bt5840Isup3.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
C16—H16⋯O1ⁱ	0.93	2.56	3.418 (2)	154

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Symmetry code: (i) Inline graphic .

Acknowledgments

We thank the Analytical and Testing Center of Sichuan University for the X-ray measurements.

supplementary crystallographic information

Comment

1-(2-Methyl-benzyl)-1H-indole-3-carbaldehyde is of great importance owing to its wide biological properties (Andreani et al., 1994). The title compound is one of the key intermediates in our synthetic investigations of antibacterial drugs. We report here its crystal structure.

In the title compound, C₁₇H₁₅NO, as shown in Fig 1, the benzene ring with the methyl group in ortho position and the indole system are almost perpendicular, making dihedral angle of 87.82 (6)°. A combination of intermolecular C-H···O and π–π packing interaction plays an important role in the connection of neighbouring molecules. The centroid-centroid distance between the pyrrole ring and the benzene ring in the indole system of the neighbouring molecule is 3.592 (4) Å (symmetry operator: -x, -y, -z).

Experimental

1H-indole-3-carbaldehyde(14 mmol) was dissolved in dry DMF(25 ml)and treated portionwise,under stirring, with 20 mmol NaH. The mixture was stirred at room temperature for 10 min and treated with 20 mmol of 1-chloromethyl-2-methyl-benzene. After 1 h at 90°C under stirring, the mixture was poured onto ice. The resulting precipitate was collected by filtration and crystallized from ethanol with a yield of 70%. Crystals suitable for X-ray analysis were obtained by slow evaporation from a solution of dichloromethane.