rac-5-Acetyl-6-hy­droxy-3,6-dimethyl-4-phenyl-2H-4,5,6,7-tetra­hydro­indazol-1-ium chloride

Abel M Maharramov; Arif I Ismiyev; Bahruz A Rashidov; Rizvan K Askerov; Victor N Khrustalev

doi:10.1107/S1600536810024281

. 2010 Jun 26;66(Pt 7):o1848. doi: 10.1107/S1600536810024281

rac-5-Acetyl-6-hydroxy-3,6-dimethyl-4-phenyl-2H-4,5,6,7-tetrahydroindazol-1-ium chloride

Abel M Maharramov ^a, Arif I Ismiyev ^a, Bahruz A Rashidov ^a,^*, Rizvan K Askerov ^a, Victor N Khrustalev ^b

PMCID: PMC3006733 PMID: 21588046

Abstract

The structure of the title compound, C₁₇H₂₁N₂O₂ ⁺·Cl⁻, is of interest with respect to its biological activity. The title compound comprises an organic cation and a chloride anion in the asymmetric unit. The positive charge is localized in a pyrazole moiety forming a pyrazolium cation. The structure displays intermolecular O—H⋯Cl and N—H⋯Cl hydrogen bonding.

Related literature

For general background, see: Raptis et al. (1993 ▶); Rabe (1904 ▶).

Experimental

Crystal data

C₁₇H₂₁N₂O₂ ⁺·Cl⁻
M _r = 320.81
Triclinic,
a = 6.9661 (3) Å
b = 8.3527 (4) Å
c = 15.6739 (7) Å
α = 88.145 (1)°
β = 87.385 (1)°
γ = 67.882 (1)°
V = 843.89 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 296 K
0.30 × 0.30 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T _min = 0.933, T _max = 0.955
9861 measured reflections
4188 independent reflections
3279 reflections with I > 2σ(I)
R _int = 0.015

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.130
S = 1.00
4188 reflections
199 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810024281/kp2265sup1.cif

e-66-o1848-sup1.cif^{(19.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810024281/kp2265Isup2.hkl

e-66-o1848-Isup2.hkl^{(205.2KB, 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
O1—H1A⋯Cl	0.82	2.39	3.2110 (14)	176
N2—H2B⋯Cl	0.86	2.21	3.0620 (14)	171
N1—H1B⋯Cl	0.86	2.25	3.0280 (15)	150

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Acknowledgments

We thank Professor Abel M. Maharramov for fruitful discussions and help with this work.

supplementary crystallographic information

Comment

(rac)-5-Acetyl-6-hydroxy-3,6-dimethyl-4-phenyl-2H-4,5,6,7- tetrahyroindazolium chloride (I) have good antibacterial and biological properties. We have synthesised the title compound, (I), and its structure is reported here (Fig. 1). The two [(C2(R),C4(R)] of three stereogenic centres of tetrahydroindazole moiety are of the same chirality. As the crystal crystallises in the centrosymmetric space group, the racemate (1:1) is present. The crystal structure involves O—H···Cl, and N—H···C intermolecular hydrogen bonds (Table 1 and Fig. 2).

Experimental

2,4-Diacetyl-5-hydroxy-5-methyl-3-phenylcyclohexanon (20 mmol)and hydrazine hydrate (20 mmol) were dissolved in 20 ml ethanol. The mixture was stirred at 340 K within 10 h. Through suspension in absolute toluene a flow of dry gaseous hydrogen chloride was used at 278-283 K. From a solution a white solid was obtained. A crude product was filtered and washed with ethanol. Then, the crude product was dissolved in ethanol (50 ml) and recrystallised to yield colourless block-shaped crystals of (I).