(E)-2-[(Furan-2-yl)methyl­idene]-7-methyl-2,3,4,9-tetra­hydro-1H-carbazol-1-one

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

doi:10.1107/S1600536812051203

. 2013 Jan 4;69(Pt 2):o150. doi: 10.1107/S1600536812051203

(E)-2-[(Furan-2-yl)methylidene]-7-methyl-2,3,4,9-tetrahydro-1H-carbazol-1-one

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

PMCID: PMC3569219 PMID: 23424442

Abstract

In the title molecule, C₁₈H₁₅NO₂, the atoms in the carbazole unit deviate from planarity [maximum deviation from mean plane = 0.1317 (12) Å]. The pyrrole ring makes dihedral angles of 1.01 (8) and 18.56 (10)° with the benzene and furan rings, respectively. The cyclohexene ring adopts a half-chair conformation. In the crystal, pairs of N—H⋯O hydrogen bonds form an R ₂ ²(10) ring. Molecules are further linked by C—H⋯O and C—H⋯π interactions, forming a three-dimensional network.

Related literature

For a related structure and the synthesis and applications of carbazole derivatives, see: Archana et al. (2010 ▶). For ring conformations, see: Cremer & Pople (1975 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). graphic file with name e-69-0o150-scheme1.jpg

Experimental

Crystal data

C₁₈H₁₅NO₂
M _r = 277.31
Triclinic,
a = 6.3925 (3) Å
b = 7.9880 (4) Å
c = 13.8629 (8) Å
α = 83.151 (5)°
β = 81.649 (4)°
γ = 78.921 (4)°
V = 684.28 (6) Å³
Z = 2
Cu Kα radiation
μ = 0.70 mm⁻¹
T = 123 K
0.34 × 0.26 × 0.12 mm

Data collection

Agilent Xcalibur Ruby Gemini diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ▶) T _min = 0.816, T _max = 1.000
4371 measured reflections
2724 independent reflections
2382 reflections with I > 2σ(I)
R _int = 0.021

Refinement

R[F ² > 2σ(F ²)] = 0.047
wR(F ²) = 0.132
S = 1.05
2724 reflections
199 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS86 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97 and PLATON.

Supplementary Material

Click here for additional data file.^{(19.9KB, cif)}

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812051203/tk5183sup1.cif

e-69-0o150-sup1.cif^{(19.9KB, cif)}

Click here for additional data file.^{(131KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812051203/tk5183Isup2.hkl

e-69-0o150-Isup2.hkl^{(131KB, hkl)}

Click here for additional data file.^{(3.7KB, cdx)}

Supplementary material file. DOI: 10.1107/S1600536812051203/tk5183Isup3.cdx

Click here for additional data file.^{(5.8KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536812051203/tk5183Isup4.cml

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

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

Cg2 and Cg1 are the centroids of the pyrrole (N9/C9A/C4A/C4B/C8A) and furan (O11/C12–C15)rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N9—H9⋯O1ⁱ	0.867 (18)	1.961 (18)	2.8069 (17)	164.9 (17)
C14—H14⋯O1ⁱⁱ	0.95	2.55	3.250 (2)	130
C4—H4B⋯Cg2ⁱⁱⁱ	0.99	2.60	3.5176 (16)	154
C17—H17B⋯Cg1ⁱⁱⁱ	0.98	2.89	3.807 (2)	156

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

Acknowledgments

RJB acknowledges the NSF–MRI program (grant No. CHE0619278) for funds to purchase the X-ray diffractometer. SKG wishes to thank the USIEF for the award of a Fulbright–Nehru Senior Fellowship.

supplementary crystallographic information

Comment

As part of our research (Archana et al., 2010), we have synthesized the title compound (I), and report its crystal structure here.

In the title molecule (Fig. 1), C₁₈H₁₅NO₂, the carbazole unit is not planar. Maximum deviation from carbazole mean plane = -0.1317 (12) Å for atom C4. All bond lengths and angles in (I) are normal and comparable with those observed in the related (E)-2-(furan-2-ylmethylidene)-8-methyl-2,3,4,9-tetrahydro-1H- carbazol-1-one (Archana et al., 2010). The pyrrole ring makes dihedral angles of 1.01 (8) and 18.56 (10)° with the benzene and the furan rings, respectively. The cyclohexene ring adopts a half-chair conformation. The puckering parameters (Cremer & Pople, 1975) are q2 = 0.1372 (15) Å, q3 = 0.1060 (15) Å, Q = 0.1734 (15) Å, θ = 52.3 (5)° and φ = 143.0 (6)°. Intermolecular N9—H9···O1 hydrogen bonds form a R²₂(10) (Bernstein et al., 1995) ring motif in the crystal structure (Table 1, Fig. 2). Further, molecules are linked by intermolecular C14—H14···O1, C4—H4B···π, involving the pyrrole (N9/C9A/C4A/C4B/C8A) ring, and C17—H17B···π, involving the furan (O11/C12—C15) ring, interaction to form a three-dimensional architecture (Table 1, Figs 2 & 3).

Experimental

An equimolar mixture of 7-methyl-2,3,4,9-tetrahydro-1H-carbazol-1-one (0.995 g, 0.005 mol) and furan-2-carbaldehyde (0.414 g, 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 95% (1.315 g) of the title compound. The pure compound was recrystallized from EtOAc and ethanol.