(4,9-Dimethyl-9H-carbazol-3-yl)meth­anol

Serkan Öncüoğlu; Nefise Dilek; Yavuz Ergün; Tuncer Hökelek

doi:10.1107/S1600536814003845

. 2014 Feb 22;70(Pt 3):o346–o347. doi: 10.1107/S1600536814003845

(4,9-Dimethyl-9H-carbazol-3-yl)methanol

Serkan Öncüoğlu ^a, Nefise Dilek ^b, Yavuz Ergün ^a, Tuncer Hökelek ^c,^*

PMCID: PMC3998416 PMID: 24765037

Abstract

In the title compound, C₁₅H₁₅NO, the carbazole skeleton includes a methanol group at the 3-position. The indole ring system is almost planar [maximum deviation = 0.045 (2) Å]. In the crystal, O—H⋯O hydrogen bonds link the molecules into zigzag chains along the b-axis direction. There are weak C—H⋯π interactions within the chains and linking neighbouring chains forming sheets lying parallel to (001).

Related literature

For biological activity of carbazole alkaloids, see: Chakraborty (1977 ▶). For antibiotic, antifungal and cytotoxic properties of carbazole alkaloids, see: Chakraborty et al. (1965 ▶); Chakraborty et al. (1978 ▶). For the use of carbazole derivatives as precursor compounds for the syntheses of pyridocarbazole alkaloids, see: Karmakar et al. (1991 ▶). For related structures, see: Hökelek et al. (1994 ▶); Patır et al. (1997 ▶); Öncüoğlu et al. (2014 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₅H₁₅NO
M _r = 225.28
Monoclinic,
a = 14.4728 (4) Å
b = 5.4554 (3) Å
c = 15.0906 (4) Å
β = 95.453 (4)°
V = 1186.08 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 296 K
0.45 × 0.36 × 0.13 mm

Data collection

Bruker SMART BREEZE CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T _min = 0.965, T _max = 0.990
11615 measured reflections
11615 independent reflections
9784 reflections with I > 2σ(I)
R _int = 0.032

Refinement

R[F ² > 2σ(F ²)] = 0.079
wR(F ²) = 0.214
S = 1.16
11615 reflections
161 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536814003845/su2701sup1.cif

e-70-0o346-sup1.cif^{(22.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814003845/su2701Isup2.hkl

e-70-0o346-Isup2.hkl^{(556.5KB, hkl)}

Click here for additional data file.^{(5KB, cml)}

Supporting information file. DOI: 10.1107/S1600536814003845/su2701Isup3.cml

CCDC reference: http://scripts.iucr.org/cgi-bin/cr.cgi?rm=csd&csdid=987850

Additional supporting information: crystallographic information; 3D view; checkCIF report

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

Cg1 and Cg2 are the centroids of rings 9a/C1-C4/C4a/ and C5a/C5-C8/C8a, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯O1ⁱ	0.88 (3)	2.13 (3)	2.919 (2)	149 (3)
C10—H10A⋯Cg2ⁱⁱ	0.96	2.85	3.697 (2)	148
C10—H10B⋯Cg1ⁱⁱⁱ	0.96	2.64	3.531 (2)	154
C11—H11A⋯Cg2^iv	0.96	2.77	3.617 (2)	147

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

Acknowledgments

The authors acknowledge the Aksaray University, Science and Technology Application and Research Center, Aksaray, Turkey, for the use of the Bruker SMART BREEZE CCD diffractometer (purchased under grant No. 2010K120480 of the State of Planning Organization).

supplementary crystallographic information

1. Comment

Carbazole alkaloids, which have their richest source in species of the genus Murraya, are of great interest because of their unique structures and important biological activities (Chakraborty, 1977). They also exhibits antibiotic, antifungal and cytotoxic properties (Chakraborty et al., 1965; Chakraborty et al., 1978). Carbazole derivatives are also used as precursor compounds for the syntheses of pyridocarbazole alkaloids (Karmakar et al., 1991). The present study was undertaken to ascertain the crystal structure of the title compound which was first synthesized by (Karmakar et al., 1991).

The molecule of the title compound contains a carbazole skeleton with a methanol group at the 3 position, Fig. 1. The bond lengths are close to standard values (Allen et al., 1987) and generally agree with those in previously reported compounds (Hökelek et al., 1994; Patır et al., 1997; Öncüoğlu et al., 2014). In all structures atom N9 is substituted.

An examination of the deviations from the mean planes through individual rings shows that rings A (C1—C4/C4a/c9a), B (C4a/C5a/C8a/N9/C9a) and C (C5a/C5—C8/C8a) are nearly coplanar [with a maximum deviation of 0.045 (2) Å for atom C7] with dihedral angles of A/B = 0.76 (5), A/C = 2.33 (4) and B/C = 1.57 (5) °. Atoms C10, C11 and C12 are displaced by 0.070 (2), 0.004 (2) and -0.025 (2) Å from the adjacent ring planes.

In the crystal, O—H···O hydrogen bonds link the molecules into zigzag chains along the b-axis direction (Table 1 and Fig. 2). There are weak C—H···π interactions within the chains and linking neighbouring chains forming two-dimensional networks lying parallel to (001); see Table 1.

2. Experimental

The title compound was synthesized according to the literature method (Karmakar et al., 1991). A solution of ethyl 4,9-dimethyl-9H-carbazole-3 -carboxylate (4.00 g, 15 mmol) in anhydrous tetrahydrofurane (50 ml) was added drop wise to a stirred solution of lithium aluminium hydride (1.20 g, 31 mmol) in tetrahydrofurane at room temperature. The reaction mixture was refluxed for 5 h under a nitrogen atmosphere, and then cooled and the excess of lithium aluminium hydride was destroyed with water and extracted with ethyl acetate. The organic phase was dried with anhydrous magnesium sulfate, and the solvent was evaporated. The crude product was recrystallized from ether (Yield; 95%, M.p. 475 K), giving block-like colourless crystals suitable for X-ray diffraction analysis.