2-Chloro-7,8,9,10-tetra­hydro­cyclo­hepta­[b]indol-6(5H)-one

R Archana; E Yamuna; K J Rajendra Prasad; A Thiruvalluvar; R J Butcher; Sushil K Gupta; Sema Öztürk Yildirim

doi:10.1107/S1600536812022945

. 2012 May 26;68(Pt 6):o1887. doi: 10.1107/S1600536812022945

2-Chloro-7,8,9,10-tetrahydrocyclohepta[b]indol-6(5H)-one

R Archana ^a, E Yamuna ^b, K J Rajendra Prasad ^b, A Thiruvalluvar ^a,^*, R J Butcher ^c, Sushil K Gupta ^d, Sema Öztürk Yildirim ^e,^f

PMCID: PMC3379447 PMID: 22719645

Abstract

In the title molecule, C₁₃H₁₂ClNO, the dihedral angle between the benzene and pyrrole rings is 1.38 (9)°. The cycloheptene ring adopts a distorted twist chair and sofa conformation. Intermolecular N—H⋯O hydrogen bonds form an R ₂ ²(10) loop in the crystal packing. Further, weak C—H⋯O and C—H⋯π (involving the benzene ring) interactions are found in the crystal structure.

Related literature

For the biological activity of indole derivatives, see: Gribble (2000 ▶); Knölker & Reddy (2002 ▶); Kawasaki & Higuchi (2005 ▶); Bennasar et al. (1993 ▶); Hong et al. (2006 ▶); Lacoume et al. (1972 ▶); Joseph et al. (1998 ▶, 2000 ▶). For related crystallographic studies of cyclohept[b]indoles, see: Archana et al. (2010 ▶, 2011 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). graphic file with name e-68-o1887-scheme1.jpg

Experimental

Crystal data

C₁₃H₁₂ClNO
M _r = 233.69
Monoclinic,
a = 11.6354 (4) Å
b = 6.3798 (2) Å
c = 14.4513 (5) Å
β = 92.767 (3)°
V = 1071.49 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.33 mm⁻¹
T = 150 K
0.40 × 0.30 × 0.30 mm

Data collection

Agilent Xcalibur Ruby Gemini diffractometer
Absorption correction: multi-scan CrysAlis PRO (Agilent, 2011 ▶) T _min = 0.879, T _max = 0.907
4977 measured reflections
2274 independent reflections
1836 reflections with I > 2σ(I)
R _int = 0.026

Refinement

R[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 0.096
S = 1.04
2274 reflections
149 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.26 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: ORTEP-3 (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: PLATON.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812022945/tk5099sup1.cif

e-68-o1887-sup1.cif^{(17.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812022945/tk5099Isup2.hkl

e-68-o1887-Isup2.hkl^{(109.5KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812022945/tk5099Isup3.cdx

Supplementary material file. DOI: 10.1107/S1600536812022945/tk5099Isup4.cml

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

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

Cg2 is the centroid of the C1–C4,C4A,C10B ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N5—H5⋯O6ⁱ	0.837 (19)	2.13 (2)	2.904 (2)	153.2 (19)
C9—H9A⋯O6ⁱⁱ	0.99	2.55	3.228 (2)	125
C7—H7A⋯Cg2ⁱⁱⁱ	0.99	2.95	3.7969 (19)	144

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

Acknowledgments

RJB acknowledges the NSF MRI program (grant No. CHE-0619278) for funds to purchase an X-ray diffractometer.

supplementary crystallographic information

Comment

An indole nucleus coupled with prenylated indoles, carbazoles, indoloquinoline and cyclohept[b]indole alkaloids show high levels of biological activities including anti-fungal, anti-bacterial, anti-tumour and anti-HIV activities, as well as DNA interaction properties (Gribble, 2000; Knölker & Reddy, 2002; Kawasaki & Higuchi, 2005; Bennasar et al., 1993; Hong et al., 2006; Lacoume et al., 1972; Joseph et al., 1998; Joseph et al., 2000). Recently, we reported related crystallographic studies for some cyclohept[b]indoles from our laboratory (Archana et al., 2010; Archana et al., 2011).

In the title molecule, Fig. 1, the dihedral angle between the benzene and pyrrole rings is 1.38 (9)°. The cycloheptene ring adopts a distorted twist chair and sofa conformation. Intermolecular N5—H5···O6 hydrogen bonds form a R²₂(10) (Bernstein et al., 1995) rings in the crystal structure. A weak C9—H9A···O6 intermolecular hydrogen bond along with a C7—H7A···π interaction, involving the benzene (C1–C4,C4A,C10B) ring, are also found in the crystal structure, Fig. 2 and Table 1.

Experimental

A solution of 2-(2-(4-chlorophenyl)hydrazono)cycloheptanone (0.486 g, 0.001 mol) in a mixture of acetic acid (20 ml) and hydrochloric acid (5 ml) was refluxed on an oil bath pre-heated to 398 K for 2 h. The contents were then cooled and poured onto cold water with stirring. The brown solid which was separated by passing through a column of silica gel and eluted with (98:2, v/v) petroleum ether-ethyl acetate mixture yielded the title compound (0.167 g, 72%). This was recrystallized from ethanol.