(E)-6-Chloro-2-(furan-2-yl­methyl­idene)-2,3,4,9-tetra­hydro-1H-carbazol-1-one

R Archana; E Yamuna; K J Rajendra Prasad; A Thiruvalluvar; R J Butcher

doi:10.1107/S1600536810046714

. 2010 Nov 17;66(Pt 12):o3198. doi: 10.1107/S1600536810046714

(E)-6-Chloro-2-(furan-2-ylmethylidene)-2,3,4,9-tetrahydro-1H-carbazol-1-one

R Archana ^a, E Yamuna ^b, K J Rajendra Prasad ^b, A Thiruvalluvar ^a,^*, R J Butcher ^c

PMCID: PMC3011405 PMID: 21589492

Abstract

In the title compound, C₁₇H₁₂ClNO₂, the carbazole unit is nearly planar [maximum deviation = 0.052 (1) Å]. The pyrrole ring makes dihedral angles of 1.92 (8) and 4.71 (11)° with the benzene and furan rings, respectively. Intermolecular N—H⋯O hydrogen bonds form R ₂ ²(10) rings in the crystal structure.

Related literature

For the pharmaceutical interest of heteroaryl annulated derivatives of carbazoles, see: Knölker & Reddy (2002 ▶, 2008 ▶). For the preparation of various hetero-annulated carbazoles, see: Sridharan et al. (2008 ▶); Danish & Rajendra Prasad (2004 ▶, 2005 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₇H₁₂ClNO₂
M _r = 297.73
Monoclinic,
a = 15.0985 (2) Å
b = 6.1553 (1) Å
c = 15.3887 (2) Å
β = 104.319 (1)°
V = 1385.73 (3) Å³
Z = 4
Cu Kα radiation
μ = 2.47 mm⁻¹
T = 295 K
0.48 × 0.34 × 0.12 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T _min = 0.389, T _max = 1.000
8660 measured reflections
2834 independent reflections
2676 reflections with I > 2σ(I)
R _int = 0.026

Refinement

R[F ² > 2σ(F ²)] = 0.047
wR(F ²) = 0.139
S = 1.10
2834 reflections
194 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); 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 datablocks global, I. DOI: 10.1107/S1600536810046714/bq2253sup1.cif

e-66-o3198-sup1.cif^{(21KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810046714/bq2253Isup2.hkl

e-66-o3198-Isup2.hkl^{(136.3KB, hkl)}

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
N9—H9⋯O1ⁱ	0.88 (2)	1.94 (2)	2.7935 (17)	164 (2)

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Symmetry code: (i) Inline graphic .

Acknowledgments

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

supplementary crystallographic information

Comment

Aryl and heteroarylcarbazoles are important classes of biologically active compounds that include notable alkaloids of pharmaceutical interest (Knölker & Reddy (2002, 2008)) and heteroaryl annulated derivatives of carbazole. From our laboratory, we have reported the synthesis of 2-benzylidene-2,3,4,9-tetrahydrocarbazoles from the precursors of the 2,3,4,9-tetrahydro-1H-carbazol-1-one type and these synthons were utilized to prepare many heteroannulated carbazoles (Sridharan et al., (2008); Danish & Rajendra Prasad (2004, 2005)).

In the title molecule (Fig. 1), C₁₇H₁₂ClNO₂, the carbazole unit is nearly planar [maximum deviation = 0.052 (1) Å for C1]. The pyrrole ring makes dihedral angles of 1.92 (8)° and 4.71 (11)° with the benzene and the furan rings, respectively. Intermolecular N9—H9···O1 hydrogen bonds form a R₂²(10) (Bernstein et al., 1995) ring in the crystal structure (Table 1, Fig. 2).

Experimental

An equimolar mixture of 6-chloro-2,3,4,9-tetrahydro-1H-carbazol-1-one (1.095 g, 0.005 mol) and furan-2-carbaldehyde (0.41 ml, 0.005 mol) was treated with 25 ml of a 5% ethanolic potassium hydroxide solution and stirred for 6 h at room temperature. The product precipitated as a yellow crystalline mass, was filtered off and washed with 50% ethanol. A further crop of condensation product was obtained on neutralization with acetic acid and dilution with water. The product was recrystallized from methanol to yield 90% (1.336 g) of the title compound. The pure compound was recrystallized from EtOAc.