3-Acetyl-6-chloro-2-methyl-4-phenyl­quinolinium perchlorate

Tara Shahani; Hoong-Kun Fun; S Sarveswari; V Vijayakumar; B Palakshi Reddy

doi:10.1107/S1600536810012900

. 2010 Apr 28;66(Pt 5):o1192–o1193. doi: 10.1107/S1600536810012900

3-Acetyl-6-chloro-2-methyl-4-phenylquinolinium perchlorate

Tara Shahani ^a, Hoong-Kun Fun ^a,^*,^‡, S Sarveswari ^b, V Vijayakumar ^b, B Palakshi Reddy ^b

PMCID: PMC2979191 PMID: 21579229

Abstract

In the title molecular salt, C₁₈H₁₅ClNO⁺·ClO₄ ⁻, the quinolinium ring system is approximately planar, with a maximum deviation of 0.027 (1) Å. The dihedral angle formed between the mean planes of the quinolinium ring system and the benzene ring is 78.46 (3)°. In the crystal structure, intermolecular N—H⋯O and C—H⋯O hydrogen bonds link the cations and anions into a three-dimensional network. The crystal structure is further consolidated by C—H⋯π interactions.

Related literature

For natural products containing quinolines, see: Michael (1997 ▶); Morimoto et al. (1991 ▶). For the biological activities of quinolines, see: Campbell et al. (1988 ▶); Markees et al. (1970 ▶). For the physiological activities of quinolines, see: Katritzky & Arend (1998 ▶); Jiang & Si (2002 ▶). For related structures, see: Shahani et al. (2010 ▶); Fun et al. (2009 ▶); Loh et al. (2010 ▶). For bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C₁₈H₁₅ClNO⁺·ClO₄ ⁻
M _r = 396.21
Triclinic,
a = 7.3862 (1) Å
b = 8.8519 (2) Å
c = 13.3378 (3) Å
α = 92.477 (1)°
β = 91.903 (1)°
γ = 99.550 (1)°
V = 858.44 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.41 mm⁻¹
T = 100 K
0.58 × 0.54 × 0.27 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.797, T _max = 0.898
27967 measured reflections
7482 independent reflections
6933 reflections with I > 2σ(I)
R _int = 0.019

Refinement

R[F ² > 2σ(F ²)] = 0.031
wR(F ²) = 0.108
S = 1.09
7482 reflections
295 parameters
All H-atom parameters refined
Δρ_max = 0.69 e Å⁻³
Δρ_min = −1.00 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; 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 and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810012900/hb5397sup1.cif

e-66-o1192-sup1.cif^{(20.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810012900/hb5397Isup2.hkl

e-66-o1192-Isup2.hkl^{(366KB, hkl)}

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

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

Cg1 is the centroid of the C10–C15 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O3ⁱ	0.832 (18)	1.896 (18)	2.7177 (10)	169 (2)
C3—H3A⋯O2ⁱⁱ	0.955 (16)	2.583 (16)	3.3010 (11)	132.2 (12)
C15—H15A⋯O5	0.951 (16)	2.512 (16)	3.3716 (12)	150.4 (13)
C18—H18B⋯O5ⁱⁱⁱ	0.97 (2)	2.53 (2)	3.3266 (13)	139.5 (14)
C12—H12A⋯Cg1^iv	0.981 (17)	2.694 (17)	3.5810 (10)	150.6 (13)

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

Acknowledgments

TSH and HKF thank the Universiti Sains Malaysia (USM) for Research University Golden Goose grant No. 1001/PFIZIK/811012. VV is grateful to the DST, India, for funding through the Young Scientist Scheme (Fast Track Proposal).

supplementary crystallographic information

Comment

Quinolines and their derivatives are very important compounds because of their wide occurrence in natural products (Morimoto et al., 1991; Michael, 1997), and biologically active compounds (Markees et al., 1970 ; Campbell et al., 1988). A large variety of quinolines have interesting physiological activities and found attractive applications as pharmaceuticals, agrochemicals and as synthetic building blocks, due to their great importance, the synthesis of new derivatives of quinoline remains an active research area (Katritzky & Arend, 1998; Jiang & Si, 2002).

In the title compound (Fig. 1), the asymmetric unit consists one perchlorate anion and one 3-acetyl-6-chloro-2-methyl-4-phenlquineline-1-ium cation. The quinolinium ring system (C1/N1/C2–C9) is approximately planar, with a maximum deviation of 0.027 (1) Å at atom C1. The dihedral angle formed between quinolinium ring system and benzene ring (C10–C15) is 78.46 (3)°. Bond lengths (Allen et al., 1987) and angles are normal and comparable to those related structures (Shahani et al., 2010; Fun et al., 2009; Loh et al., 2010).

In the crystal packing (Fig. 2), intermolecular N1—H1N1···O3, C3—H3A···O2, C15—H15A···O5 and C18—H18B···O5 hydrogen bonds (Table 1) link the molecules into three-dimensional network. This crystal structure is further consolidated by C—H···π interactions involving C10–C15 benzene ring (centroid Cg1).

Experimental

A mixture of 3-acetyl-6-chloro-2-methyl-4-phenylquinoline and a catalytic amount of nickel chloride in acid medium was refluxed for about an hour and resultant compound was recrystallized from 3:1 ethanol water to yield colourless blocks of (I).