

Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807034307/ww2091sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536807034307/ww2091Isup2.hkl |
CCDC reference: 657788
The mixture of 2,3,4,9-tetrahydro-1H-carbazol-1-one (185 mg, 0.001 mol), methyl iodide (1 ml) and ignited potassium carbonate (276 mg, 0.002 mol) in dry acetone (20 ml) was refluxed on a steam bath for 3 h. The reaction was monitored by TLC. After completion of the reaction, the solvent was removed by distillation and the mixture was poured into crushed ice. The solid obtained was filtered, washed with water and dried. It was purified by column chromatography over silica gel (60–120 mesh) using petroleum ether/ethyl acetate (98:2) as eluant to get the pure title compound (106 mg, 54%). It was recrystallized from petroleum ether/ethylacetate (90:10).
Owing to the absence of any anomalous scatterers in the molecule, the Friedel pairs were merged. The absolute structure in the present model have been chosen arbitrarily. H atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H = 0.94–0.98 Å and Uiso(H) = 1.2–1.5 times Ueq(C). The methyl group was treated as an idealized disordered methyl group over two positions; coordinates riding with C—H = 0.97 Å and Uiso(H) = 1.5times Ueq(C9).
Indole and its various substituted products have long been known for their interesting chemical and biological activities (Chandrakantha et al., 1992). The indole ring system is present in a number of natural products, many of which are found to possess pharmacological properties like anti-microbial, anti-inflammatory and anti-implantation activities (Rodriguez et al., 1985; Ebenezer Martin & Rajendra Prasad, 2006; Balamurali & Rajendra Prasad, 2001). Carbazoles formed by the fusion of indole ring with aromatic six-membered ring, are also widely used in many areas in biological sciences. The structures of these derivatives are analogous to that of ellipticine, a plant alkaloid having pronounced anti-tumour activity and are found to have DNA intercalating properties (Courseille et al., 1974). Synthetic approaches to substituted carbazoles are of special interest and contemporary importance since the growing variety of carbazole alkaloids isolated show anti-microbial, anti-viral (Tubingensin A) and cytotoxic properties (Tubingensin B: a cytotoxic Carbazole alkaloid) against consumption of the sclerotia by insects (Govindasamy et al., 2003). Benzo- and pyrido-annulated carbazoles are pharmacologically interesting since such compounds have potential for the development of compounds with anti-tumor activity. From the above findings it is concluded that the title compound can act as an important synthon to derive such active carbazoles.
Gunaseelan et al. (2007a,b) have reported crystal structures of substituted carbazole derivatives, wherein the carbazole units are not planar. The molecular structure of the title compound, with atomic numbering scheme, is shown in Fig. 1. The carbazole unit is not planar. The dihedral angle between the benzene ring and the fused pyrrole ring is 2.5 (1)°. The cyclohexene ring is in envelope form. There is an intramolecular C9—H9A···O1 hydrogen bond.
Several authors (Chandrakantha et al., 1992; Rodriguez et al., 1985; Ebenezer Martin & Rajendra Prasad, 2006; Balamurali & Rajendra Prasad, 2001; Courseille et al., 1974; Govindasamy et al., 2003; Gunaseelan et al., 2007a,b) have reported crystal structures of substituted carbazole derivatives, wherein the carbazole units are not planar.
Data collection: CrysAlis CCD (Oxford Diffraction, 2007); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2003).
C13H13NO | Dx = 1.312 Mg m−3 |
Mr = 199.24 | Melting point: 453(1) K |
Orthorhombic, Pna21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2n | Cell parameters from 2548 reflections |
a = 7.4974 (5) Å | θ = 4.7–30.4° |
b = 14.9690 (11) Å | µ = 0.08 mm−1 |
c = 8.9885 (10) Å | T = 203 K |
V = 1008.77 (15) Å3 | Block, light-brown |
Z = 4 | 0.39 × 0.37 × 0.28 mm |
F(000) = 424 |
Oxford Diffraction Gemini diffractometer | 1464 independent reflections |
Radiation source: fine-focus sealed tube | 1056 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.052 |
Detector resolution: 10.5081 pixels mm-1 | θmax = 30.5°, θmin = 5.3° |
φ and ω scans | h = 0→10 |
Absorption correction: multi-scan (CrysAlis CCD or RED?; Oxford Diffraction, 2007) | k = 0→19 |
Tmin = 0.798, Tmax = 1.000 | l = 0→12 |
4884 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.044 | H-atom parameters constrained |
wR(F2) = 0.106 | w = 1/[σ2(Fo2) + (0.0626P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max < 0.001 |
1464 reflections | Δρmax = 0.21 e Å−3 |
136 parameters | Δρmin = −0.30 e Å−3 |
1 restraint | Absolute structure: see Refinement section in supplementary materials |
Primary atom site location: structure-invariant direct methods |
C13H13NO | V = 1008.77 (15) Å3 |
Mr = 199.24 | Z = 4 |
Orthorhombic, Pna21 | Mo Kα radiation |
a = 7.4974 (5) Å | µ = 0.08 mm−1 |
b = 14.9690 (11) Å | T = 203 K |
c = 8.9885 (10) Å | 0.39 × 0.37 × 0.28 mm |
Oxford Diffraction Gemini diffractometer | 1464 independent reflections |
Absorption correction: multi-scan (CrysAlis CCD or RED?; Oxford Diffraction, 2007) | 1056 reflections with I > 2σ(I) |
Tmin = 0.798, Tmax = 1.000 | Rint = 0.052 |
4884 measured reflections |
R[F2 > 2σ(F2)] = 0.044 | 1 restraint |
wR(F2) = 0.106 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.21 e Å−3 |
1464 reflections | Δρmin = −0.30 e Å−3 |
136 parameters | Absolute structure: see Refinement section in supplementary materials |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
N9 | 0.2382 (2) | 0.25379 (10) | 0.0201 (2) | 0.0289 (4) | |
C4B | 0.2697 (2) | 0.39912 (14) | −0.0453 (3) | 0.0260 (5) | |
C4A | 0.1978 (3) | 0.39569 (13) | 0.1011 (3) | 0.0250 (5) | |
C9A | 0.1816 (3) | 0.30606 (12) | 0.1380 (3) | 0.0259 (5) | |
C5 | 0.3245 (3) | 0.46894 (13) | −0.1400 (3) | 0.0308 (6) | |
H5 | 0.3115 | 0.5289 | −0.1109 | 0.037* | |
C8A | 0.2933 (3) | 0.30931 (14) | −0.0925 (3) | 0.0283 (5) | |
O1 | 0.1064 (2) | 0.19597 (10) | 0.3163 (2) | 0.0496 (5) | |
C1 | 0.1188 (3) | 0.27520 (13) | 0.2818 (3) | 0.0310 (5) | |
C4 | 0.1455 (3) | 0.46920 (13) | 0.2044 (3) | 0.0300 (6) | |
H4A | 0.0222 | 0.4874 | 0.1846 | 0.036* | |
H4B | 0.2231 | 0.5211 | 0.1888 | 0.036* | |
C8 | 0.3655 (3) | 0.28846 (14) | −0.2314 (3) | 0.0358 (6) | |
H8 | 0.3780 | 0.2288 | −0.2625 | 0.043* | |
C7 | 0.4178 (3) | 0.35812 (15) | −0.3211 (3) | 0.0389 (6) | |
H7 | 0.4681 | 0.3457 | −0.4147 | 0.047* | |
C6 | 0.3975 (3) | 0.44756 (15) | −0.2758 (3) | 0.0370 (6) | |
H6 | 0.4346 | 0.4937 | −0.3397 | 0.044* | |
C9 | 0.2415 (3) | 0.15656 (12) | 0.0102 (4) | 0.0390 (6) | |
H9A | 0.1977 | 0.1312 | 0.1026 | 0.058* | 0.50 |
H9B | 0.3628 | 0.1366 | −0.0070 | 0.058* | 0.50 |
H9C | 0.1662 | 0.1373 | −0.0714 | 0.058* | 0.50 |
H9D | 0.2867 | 0.1388 | −0.0865 | 0.058* | 0.50 |
H9E | 0.1216 | 0.1334 | 0.0231 | 0.058* | 0.50 |
H9F | 0.3183 | 0.1327 | 0.0875 | 0.058* | 0.50 |
C2 | 0.0641 (3) | 0.34836 (14) | 0.3883 (3) | 0.0376 (6) | |
H2A | 0.0856 | 0.3279 | 0.4903 | 0.045* | |
H2B | −0.0643 | 0.3589 | 0.3777 | 0.045* | |
C3 | 0.1626 (3) | 0.43645 (15) | 0.3643 (3) | 0.0384 (6) | |
H3A | 0.1139 | 0.4817 | 0.4318 | 0.046* | |
H3B | 0.2890 | 0.4284 | 0.3885 | 0.046* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0612 (10) | 0.0345 (8) | 0.0532 (13) | −0.0010 (7) | 0.0077 (11) | 0.0149 (8) |
N9 | 0.0321 (8) | 0.0220 (7) | 0.0327 (9) | −0.0002 (7) | −0.0026 (8) | 0.0005 (9) |
C1 | 0.0236 (9) | 0.0336 (11) | 0.0358 (15) | −0.0005 (8) | −0.0037 (10) | 0.0056 (9) |
C2 | 0.0394 (11) | 0.0390 (11) | 0.0345 (14) | −0.0025 (9) | 0.0046 (11) | 0.0026 (10) |
C3 | 0.0478 (12) | 0.0348 (12) | 0.0327 (15) | −0.0042 (10) | −0.0016 (12) | −0.0029 (10) |
C4 | 0.0314 (10) | 0.0261 (10) | 0.0326 (16) | −0.0001 (7) | 0.0009 (11) | −0.0024 (9) |
C4A | 0.0230 (9) | 0.0243 (9) | 0.0277 (13) | 0.0002 (8) | −0.0048 (10) | 0.0011 (9) |
C4B | 0.0223 (8) | 0.0253 (10) | 0.0304 (12) | 0.0017 (7) | −0.0043 (10) | 0.0019 (9) |
C5 | 0.0274 (9) | 0.0273 (10) | 0.0377 (16) | 0.0027 (8) | −0.0016 (11) | 0.0077 (10) |
C6 | 0.0334 (10) | 0.0410 (11) | 0.0366 (16) | 0.0035 (9) | 0.0007 (12) | 0.0140 (11) |
C7 | 0.0355 (12) | 0.0545 (14) | 0.0267 (13) | 0.0091 (9) | 0.0027 (11) | 0.0002 (11) |
C8 | 0.0345 (10) | 0.0374 (12) | 0.0355 (16) | 0.0041 (9) | −0.0041 (11) | −0.0101 (11) |
C8A | 0.0243 (9) | 0.0283 (10) | 0.0321 (15) | 0.0018 (8) | −0.0059 (10) | −0.0016 (9) |
C9 | 0.0431 (11) | 0.0213 (9) | 0.0526 (16) | 0.0018 (9) | −0.0100 (12) | −0.0033 (11) |
C9A | 0.0219 (9) | 0.0274 (10) | 0.0285 (14) | 0.0003 (8) | −0.0045 (9) | 0.0013 (9) |
O1—C1 | 1.229 (3) | C2—H2A | 0.9800 |
N9—C8A | 1.373 (3) | C2—H2B | 0.9800 |
N9—C9 | 1.458 (2) | C3—H3A | 0.9800 |
N9—C9A | 1.384 (3) | C3—H3B | 0.9800 |
C1—C2 | 1.511 (3) | C4—H4A | 0.9800 |
C1—C9A | 1.451 (4) | C4—H4B | 0.9800 |
C2—C3 | 1.527 (3) | C5—H5 | 0.9400 |
C3—C4 | 1.524 (4) | C6—H6 | 0.9400 |
C4—C4A | 1.492 (3) | C7—H7 | 0.9400 |
C4A—C4B | 1.423 (4) | C8—H8 | 0.9400 |
C4A—C9A | 1.387 (3) | C9—H9A | 0.9700 |
C4B—C5 | 1.409 (3) | C9—H9B | 0.9700 |
C4B—C8A | 1.421 (3) | C9—H9C | 0.9700 |
C5—C6 | 1.376 (4) | C9—H9D | 0.9700 |
C6—C7 | 1.408 (3) | C9—H9E | 0.9700 |
C7—C8 | 1.375 (3) | C9—H9F | 0.9700 |
C8—C8A | 1.396 (4) | ||
O1···N9 | 2.969 (3) | H3A···H9Dv | 2.4700 |
O1···C9 | 2.991 (4) | H3B···C7x | 2.9800 |
O1···H9A | 2.2600 | H3B···C9A | 3.0100 |
O1···H9E | 2.8000 | H3B···H7x | 2.5400 |
O1···H9F | 2.7700 | H4A···H3Axii | 2.5300 |
O1···H5i | 2.6600 | H4A···H9Fiv | 2.5200 |
O1···H2Bii | 2.6600 | H4B···C6xiii | 2.9000 |
O1···H7iii | 2.7000 | H4B···H6xiii | 2.5900 |
N9···O1 | 2.969 (3) | H5···H2Bxii | 2.5000 |
C8A···C9ii | 3.522 (3) | H5···O1vi | 2.6600 |
C9···O1 | 2.991 (4) | H6···H4Bvii | 2.5900 |
C9···C9Aii | 3.538 (3) | H6···C9vi | 3.0800 |
C9···C8Aiv | 3.522 (3) | H6···H9Avi | 2.3400 |
C9A···C9iv | 3.538 (3) | H6···H9Evi | 2.4700 |
C1···H9A | 2.7600 | H7···H3Bviii | 2.5400 |
C3···H9Dv | 3.0900 | H7···O1xiv | 2.7000 |
C4···H9Fiv | 3.0700 | H8···C9 | 2.8700 |
C4A···H9Biv | 2.7400 | H8···H9D | 2.1900 |
C4A···H9Fiv | 2.8800 | H9A···O1 | 2.2600 |
C4B···H9Eii | 2.7500 | H9A···C1 | 2.7600 |
C4B···H9Cii | 3.0300 | H9A···C6i | 3.0400 |
C5···H9Cii | 3.0800 | H9A···H6i | 2.3400 |
C5···H9Eii | 3.0800 | H9B···C8 | 3.0400 |
C6···H9Avi | 3.0400 | H9B···H3Aix | 2.3900 |
C6···H4Bvii | 2.9000 | H9B···C4Aii | 2.7400 |
C6···H9Cii | 3.0100 | H9B···C9Aii | 2.8500 |
C7···H3Bviii | 2.9800 | H9C···C8 | 3.0700 |
C7···H9Cii | 2.9200 | H9C···C4Biv | 3.0300 |
C7···H2Aviii | 3.0500 | H9C···C5iv | 3.0800 |
C8···H9Cii | 2.9000 | H9C···C6iv | 3.0100 |
C8···H9C | 3.0700 | H9C···C7iv | 2.9200 |
C8···H9D | 2.6600 | H9C···C8iv | 2.9000 |
C8···H9B | 3.0400 | H9C···C8Aiv | 2.9100 |
C8A···H9Eii | 2.8100 | H9D···C8 | 2.6600 |
C8A···H9Cii | 2.9100 | H9D···H8 | 2.1900 |
C9···H6i | 3.0800 | H9D···C3ix | 3.0900 |
C9···H3Aix | 2.9200 | H9D···H3Aix | 2.4700 |
C9···H8 | 2.8700 | H9E···O1 | 2.8000 |
C9A···H3B | 3.0100 | H9E···H6i | 2.4700 |
C9A···H9Biv | 2.8500 | H9E···C4Biv | 2.7500 |
C9A···H9Fiv | 2.9100 | H9E···C5iv | 3.0800 |
H2A···C7x | 3.0500 | H9E···C8Aiv | 2.8100 |
H2B···H5xi | 2.5000 | H9F···O1 | 2.7700 |
H2B···O1iv | 2.6600 | H9F···C4ii | 3.0700 |
H3A···H4Axi | 2.5300 | H9F···C4Aii | 2.8800 |
H3A···C9v | 2.9200 | H9F···C9Aii | 2.9100 |
H3A···H9Bv | 2.3900 | H9F···H4Aii | 2.5200 |
C8A—N9—C9 | 123.7 (2) | C3—C4—H4A | 110.00 |
C8A—N9—C9A | 108.33 (16) | C3—C4—H4B | 110.00 |
C9—N9—C9A | 128.0 (2) | C4A—C4—H4A | 110.00 |
O1—C1—C2 | 121.3 (2) | C4A—C4—H4B | 110.00 |
O1—C1—C9A | 123.8 (2) | H4A—C4—H4B | 108.00 |
C2—C1—C9A | 114.93 (18) | C4B—C5—H5 | 121.00 |
C1—C2—C3 | 113.9 (2) | C6—C5—H5 | 121.00 |
C2—C3—C4 | 111.7 (2) | C5—C6—H6 | 119.00 |
C3—C4—C4A | 109.12 (18) | C7—C6—H6 | 119.00 |
C4—C4A—C4B | 130.42 (19) | C6—C7—H7 | 119.00 |
C4—C4A—C9A | 122.8 (2) | C8—C7—H7 | 119.00 |
C4B—C4A—C9A | 106.8 (2) | C7—C8—H8 | 121.00 |
C4A—C4B—C5 | 134.1 (2) | C8A—C8—H8 | 121.00 |
C4A—C4B—C8A | 106.8 (2) | N9—C9—H9A | 109.00 |
C5—C4B—C8A | 119.0 (2) | N9—C9—H9B | 109.00 |
C4B—C5—C6 | 118.7 (2) | N9—C9—H9C | 109.00 |
C5—C6—C7 | 121.4 (2) | N9—C9—H9D | 109.00 |
C6—C7—C8 | 121.4 (2) | N9—C9—H9E | 109.00 |
C7—C8—C8A | 117.7 (2) | N9—C9—H9F | 109.00 |
N9—C8A—C4B | 108.4 (2) | H9A—C9—H9B | 109.00 |
N9—C8A—C8 | 129.8 (2) | H9A—C9—H9C | 109.00 |
C4B—C8A—C8 | 121.8 (2) | H9A—C9—H9D | 141.00 |
N9—C9A—C1 | 126.99 (17) | H9A—C9—H9E | 56.00 |
N9—C9A—C4A | 109.7 (2) | H9A—C9—H9F | 56.00 |
C1—C9A—C4A | 123.3 (2) | H9B—C9—H9C | 109.00 |
C1—C2—H2A | 109.00 | H9B—C9—H9D | 56.00 |
C1—C2—H2B | 109.00 | H9B—C9—H9E | 141.00 |
C3—C2—H2A | 109.00 | H9B—C9—H9F | 56.00 |
C3—C2—H2B | 109.00 | H9C—C9—H9D | 56.00 |
H2A—C2—H2B | 108.00 | H9C—C9—H9E | 56.00 |
C2—C3—H3A | 109.00 | H9C—C9—H9F | 141.00 |
C2—C3—H3B | 109.00 | H9D—C9—H9E | 109.00 |
C4—C3—H3A | 109.00 | H9D—C9—H9F | 109.00 |
C4—C3—H3B | 109.00 | H9E—C9—H9F | 109.00 |
H3A—C3—H3B | 108.00 | ||
C9—N9—C8A—C4B | 179.30 (19) | C4—C4A—C4B—C8A | −179.6 (2) |
C9—N9—C8A—C8 | −2.2 (4) | C9A—C4A—C4B—C5 | −176.2 (2) |
C9A—N9—C8A—C4B | −0.4 (2) | C9A—C4A—C4B—C8A | 0.5 (2) |
C9A—N9—C8A—C8 | 178.1 (2) | C4—C4A—C9A—N9 | 179.3 (2) |
C8A—N9—C9A—C1 | −177.6 (2) | C4—C4A—C9A—C1 | −2.4 (4) |
C8A—N9—C9A—C4A | 0.7 (3) | C4B—C4A—C9A—N9 | −0.7 (3) |
C9—N9—C9A—C1 | 2.7 (4) | C4B—C4A—C9A—C1 | 177.6 (2) |
C9—N9—C9A—C4A | −179.0 (2) | C4A—C4B—C5—C6 | 176.9 (2) |
O1—C1—C2—C3 | 152.8 (2) | C8A—C4B—C5—C6 | 0.6 (3) |
C9A—C1—C2—C3 | −28.5 (3) | C4A—C4B—C8A—N9 | 0.0 (2) |
O1—C1—C9A—N9 | −0.9 (4) | C4A—C4B—C8A—C8 | −178.7 (2) |
O1—C1—C9A—C4A | −178.9 (2) | C5—C4B—C8A—N9 | 177.21 (18) |
C2—C1—C9A—N9 | −179.5 (2) | C5—C4B—C8A—C8 | −1.5 (3) |
C2—C1—C9A—C4A | 2.4 (3) | C4B—C5—C6—C7 | 0.1 (3) |
C1—C2—C3—C4 | 54.6 (3) | C5—C6—C7—C8 | 0.0 (4) |
C2—C3—C4—C4A | −51.8 (2) | C6—C7—C8—C8A | −0.8 (3) |
C3—C4—C4A—C4B | −152.8 (2) | C7—C8—C8A—N9 | −176.8 (2) |
C3—C4—C4A—C9A | 27.2 (3) | C7—C8—C8A—C4B | 1.5 (3) |
C4—C4A—C4B—C5 | 3.8 (4) |
Symmetry codes: (i) −x+1/2, y−1/2, z+1/2; (ii) x+1/2, −y+1/2, z; (iii) x−1/2, −y+1/2, z+1; (iv) x−1/2, −y+1/2, z; (v) −x+1/2, y+1/2, z+1/2; (vi) −x+1/2, y+1/2, z−1/2; (vii) −x+1, −y+1, z−1/2; (viii) x, y, z−1; (ix) −x+1/2, y−1/2, z−1/2; (x) x, y, z+1; (xi) −x, −y+1, z+1/2; (xii) −x, −y+1, z−1/2; (xiii) −x+1, −y+1, z+1/2; (xiv) x+1/2, −y+1/2, z−1. |
Experimental details
Crystal data | |
Chemical formula | C13H13NO |
Mr | 199.24 |
Crystal system, space group | Orthorhombic, Pna21 |
Temperature (K) | 203 |
a, b, c (Å) | 7.4974 (5), 14.9690 (11), 8.9885 (10) |
V (Å3) | 1008.77 (15) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.39 × 0.37 × 0.28 |
Data collection | |
Diffractometer | Oxford Diffraction Gemini |
Absorption correction | Multi-scan (CrysAlis CCD or RED?; Oxford Diffraction, 2007) |
Tmin, Tmax | 0.798, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4884, 1464, 1056 |
Rint | 0.052 |
(sin θ/λ)max (Å−1) | 0.714 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.106, 1.02 |
No. of reflections | 1464 |
No. of parameters | 136 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.21, −0.30 |
Absolute structure | See Refinement section in supplementary materials |
Computer programs: CrysAlis CCD (Oxford Diffraction, 2007), CrysAlis CCD, CrysAlis RED (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2003).
Indole and its various substituted products have long been known for their interesting chemical and biological activities (Chandrakantha et al., 1992). The indole ring system is present in a number of natural products, many of which are found to possess pharmacological properties like anti-microbial, anti-inflammatory and anti-implantation activities (Rodriguez et al., 1985; Ebenezer Martin & Rajendra Prasad, 2006; Balamurali & Rajendra Prasad, 2001). Carbazoles formed by the fusion of indole ring with aromatic six-membered ring, are also widely used in many areas in biological sciences. The structures of these derivatives are analogous to that of ellipticine, a plant alkaloid having pronounced anti-tumour activity and are found to have DNA intercalating properties (Courseille et al., 1974). Synthetic approaches to substituted carbazoles are of special interest and contemporary importance since the growing variety of carbazole alkaloids isolated show anti-microbial, anti-viral (Tubingensin A) and cytotoxic properties (Tubingensin B: a cytotoxic Carbazole alkaloid) against consumption of the sclerotia by insects (Govindasamy et al., 2003). Benzo- and pyrido-annulated carbazoles are pharmacologically interesting since such compounds have potential for the development of compounds with anti-tumor activity. From the above findings it is concluded that the title compound can act as an important synthon to derive such active carbazoles.
Gunaseelan et al. (2007a,b) have reported crystal structures of substituted carbazole derivatives, wherein the carbazole units are not planar. The molecular structure of the title compound, with atomic numbering scheme, is shown in Fig. 1. The carbazole unit is not planar. The dihedral angle between the benzene ring and the fused pyrrole ring is 2.5 (1)°. The cyclohexene ring is in envelope form. There is an intramolecular C9—H9A···O1 hydrogen bond.