4-Methyl-1-phenyl­quinolin-2(1H)-one

Petar Yotov Petrov; Malinka Stoyanova; Boris Shivachev

doi:10.1107/S1600536807061727

. 2007 Dec 6;64(Pt 1):o72. doi: 10.1107/S1600536807061727

4-Methyl-1-phenylquinolin-2(1H)-one

Petar Yotov Petrov ^a, Malinka Stoyanova ^b, Boris Shivachev ^c,^*

PMCID: PMC2915029 PMID: 21200949

Abstract

In the title compound, C₁₆H₁₃NO, the molecules are connected three-dimensionally through non-classical C—H⋯O and C—H⋯π interactions of 3.272 (3), 3.380 (3) and 3.382 (4) Å. Classical hydrogen bonds are not observed. The dihedral angle between the benzyl and quinolin-2(1H)-one mean planes is 87.15 (7)°

Related literature

For related literature, see: Bondensgaard & Jacobsen (1999 ▶); Fürstenberg et al. (2006 ▶); Kovalska et al. (2006 ▶); Martínez & Chacón-García (2005 ▶); Perekalin & Lerner (1951 ▶); Rajnikant et al. (2002 ▶); Schenkel & Aeberli (1957 ▶); Shishkina et al. (2005 ▶); Staerk et al. (1997 ▶); Vasilev et al. (2005 ▶); Vincente et al. (2005 ▶); Zipper et al. (2004 ▶); Sheldrick & Morr (1981 ▶).

Experimental

Crystal data

C₁₆H₁₃NO
M _r = 235.27
Monoclinic,
a = 8.984 (2) Å
b = 14.194 (4) Å
c = 10.1785 (16) Å
β = 106.631 (15)°
V = 1243.7 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 290 (2) K
0.31 × 0.31 × 0.31 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: none
6212 measured reflections
2991 independent reflections
1351 reflections with I > 2σ(I)
R _int = 0.053
3 standard reflections frequency: 120 min intensity decay: none

Refinement

R[F ² > 2σ(F ²)] = 0.055
wR(F ²) = 0.160
S = 0.97
2991 reflections
164 parameters
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); Mercury (Bruno et al., 2002 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807061727/pr2017sup1.cif

e-64-00o72-sup1.cif^{(16.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807061727/pr2017Isup2.hkl

e-64-00o72-Isup2.hkl^{(143.8KB, hkl)}

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

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

Cg1 is the centroid of the C11–C16 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14⋯O1ⁱ	1.13	2.37	3.272 (3)	135
C4—H4⋯O1ⁱⁱ	1.09	2.63	3.380 (3)	125
C8—H8A⋯Cg1ⁱⁱⁱ	1.11	2.73	3.382 (4)	165

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

Acknowledgments

The authors thank the National Research Fund of Bulgaria for financial support (grant No. BYX 03.05).

supplementary crystallographic information

Comment

DNA intercalation is one of the interactions of nucleic acids with small organic molecules, through which effective antitumor agents can be designed (Martínez et al., 2005). A relevant area of research is the finding of fluorescent markers for highly sensitive DNA detection (Staerk et al., 1997; Bondensgaard et al., 1999). For the latter application, few cyanine dyes containing quinoline end-groups are established (Zipper et al., 2004), and new representatives with similar and even better efficiency were recently synthesized (Vasilev et al., 2005; Kovalska et al., 2006; Fürstenberg et al., 2006). Herein, we report the structure of (I) which is an oxo-substituted fragment of these dyes – a long known molecule (Perekalin et al., 1951).

In the unit cell of (I), only one independent molecule is present. The bond distances and angles in the benzyl and quinolin-2(1H)-one moieties are comparable to those observed in other quinolinone derivatives (Rajnikant et al., 2002; Vincente et al., 2005; Shishkina et al., 2005). The molecule posses two nearly planar ring systems [r.m.s. deviation of 0.004 (5)Å and 0.021 (4) Å for the benzyl and quinolin-2(1H)-one fragments respectively] which are capable of intercalation, attached to each other in a conformationally fluxional way. The dihedral angle between the benzyl and quinolinone mean planes is 87.15 (7) °.

In the crystal structure of (I), the molecules are connected through non-classical C—H···O hydrogen bonds and CH₃-π interactions between methyl and benzyl fragments C8—H8A···Cg1ⁱ; Cg1 is the centroid of the 1-Phenyl derivative [symmetry code (i): 1 - x, -1/2 + y, 3/2 - z]. The carbonyl O atom forms a bifurcated hydrogen bond. A head-to-tail C4—H4···O1ⁱ [symmetry code (i): x - 1,y,z] interaction between quinolinone fragments build up straight chains along a axis. A side-to-side C14—H14···O1ⁱ [symmetry code (i): 2 - x, 1/2 + y, 3/2 - z] interaction forms zigzag chains along b.

Experimental

The title compound was synthesized by dehydro-cyclization (Perekalin et al., 1951) of the respective acetoacetamide (Schenkel et al., 1957). Crystals of (I) suitable for X-ray diffraction were obtained by slow evaporation from toluene.