5-Chloro-N′-cyclo­hexyl­idene-3-methyl-1H-indole-2-carbohydrazide

Mehmet Akkurt; Muhammet Zopun; Gültaze Çapan; Orhan Büyükgüngör

doi:10.1107/S1600536813016899

. 2013 Jun 22;69(Pt 7):o1137. doi: 10.1107/S1600536813016899

5-Chloro-N′-cyclohexylidene-3-methyl-1H-indole-2-carbohydrazide

Mehmet Akkurt ^a,^*, Muhammet Zopun ^b, Gültaze Çapan ^b, Orhan Büyükgüngör ^c

PMCID: PMC3770403 PMID: 24046688

Abstract

In the title compound, C₁₆H₁₈ClN₃O, the cyclohexane ring adopts a distorted chair conformation. In the crystal, pairs of molecules are linked by N—H⋯O hydrogen bonds into inversion dimers, forming R ₂ ²(10) ring motifs. These dimers are connected through C—H⋯N hydrogen bonds into chains along the a axis, forming layers parallel to (101).

Related literature

For the design, synthesis and characterization of some bioactive indole derivatives, see: Akkurt et al. (2009 ▶, 2010 ▶); Cihan-Üstündağ & Çapan (2012 ▶); Güzel et al. (2006 ▶); Kaynak et al. (2005 ▶). For puckering analysis, see: Cremer & Pople (1975 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₆H₁₈ClN₃O
M _r = 303.78
Triclinic,
a = 5.2727 (5) Å
b = 9.7977 (9) Å
c = 15.2380 (15) Å
α = 102.229 (7)°
β = 95.732 (8)°
γ = 92.332 (7)°
V = 763.94 (13) Å³
Z = 2
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 296 K
0.76 × 0.36 × 0.02 mm

Data collection

Stoe IPDS 2 diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T _min = 0.831, T _max = 0.995
7177 measured reflections
2929 independent reflections
1684 reflections with I > 2σ(I)
R _int = 0.065

Refinement

R[F ² > 2σ(F ²)] = 0.053
wR(F ²) = 0.129
S = 1.01
2929 reflections
195 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); 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 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813016899/sj5335sup1.cif

e-69-o1137-sup1.cif^{(25.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813016899/sj5335Isup2.hkl

e-69-o1137-Isup2.hkl^{(143.7KB, hkl)}

Click here for additional data file.^{(5.9KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813016899/sj5335Isup3.cml

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
N1—H1⋯O1ⁱ	0.86	2.03	2.826 (3)	153
C12—H12B⋯N3ⁱⁱ	0.97	2.59	3.476 (4)	152

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

Acknowledgments

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDS 2 diffractometer (purchased under grant F.279 of the University Research Fund). This work was supported in part by the Scientific Research Projects Coordination Unit of Istanbul University (project No. 20867).

supplementary crystallographic information

Comment

Cyclohexylidenehydrazides are of interest, both as potential intermediates for the synthesis of novel heterocyclic systems and as pharmacologically active agents. We have recently reported on the synthesis, antitituberculosis and anticancer properties of cyclohexylidenehydrazides and spirothiazolidinones with an indole core (Cihan-Üstündağ & Çapan, 2012). As a continuation of our program directed towards the design, synthesis and characterization of bioactive indole derivatives (Akkurt et al., 2009, 2010; Güzel et al., 2006; Kaynak et al., 2005), we report here the synthesis, spectral and analytical data and crystal structure of the title compound.

In the title compound (I), (Fig. 1), the nine-membered 1H-indole ring (N1/C1–C8) is essentially planar with maximum deviations of 0.019 (3) Å for C3, 0.017 (3) Å for C7 and -0.017 (3) Å for C1]. The cyclohexane ring (C11–C16) of (I) adopts a distorted chair conformation [the puckering parameters (Cremer & Pople, 1975) are Q_T = 0.508 (4) Å, θ = 10.2 (5)° and φ = 193 (2) °]. The C7–C8–C10–N2, C7–C8–C10–O1, N1–C8–C10–O1, N1–C8–C10–N2, C8–C10–N2–N3 and C10–N2–N3–C11 torsion angles are -19.5 (5), 158.3 (3), -14.4 (4), 167.7 (3), -179.6 (2) and -172.8 (3)°, respectively.

In the crystal, pairs of N—H···O hydrogen bonds link molecules into inversion dimers, with the R²₂(10) ring motifs (Table 1, Fig. 2; Bernstein et al., 1995). These dimers connect to each other through C—H···N hydrogen bonds as chains along the a axis, forming layers parallel to the (101) plane. In the crystal structure, π-π and C—H···π interactions were not observed.

Experimental

A mixture of 5-chloro-3-methyl-1H-indole-2-carbohydrazide (0.005 mol) and cyclohexanone (0.006 mol) in 15 ml of absolute ethanol was heated under reflux for 3 h. The crude product obtained on cooling was filtered and purified by recrystallization from ethanol. [Yield: 91.4%, m.p.: 505–507 K].