8,8-Dimethyl-8,9-dihydro-7H-chromeno[2,3-b]quinoline-10,12-dione

Thothadri Srinivasan; Panneerselvam Yuvaraj; Boreddy S R Reddy; Devadasan Velmurugan

doi:10.1107/S1600536813001050

. 2013 Jan 19;69(Pt 2):o254. doi: 10.1107/S1600536813001050

8,8-Dimethyl-8,9-dihydro-7H-chromeno[2,3-b]quinoline-10,12-dione

Thothadri Srinivasan ^a, Panneerselvam Yuvaraj ^b, Boreddy S R Reddy ^b, Devadasan Velmurugan ^a,^*

PMCID: PMC3569786 PMID: 23424532

Abstract

In the title compound, C₁₈H₁₅NO₃, the fused benzopyran and pyridine rings are essentially coplanar [r.m.s. deviation = 0.0533 Å with a maximum deviation of 0.080 (1) Å for a benzene C atom]. The cyclohexanone ring adopts an envelope conformation with the dimethyl-substituted C atom 0.660 (2) Å out of the plane formed by the remaining ring atoms (r.m.s. deviation = 0.0305 Å). The dihedral angle between the mean planes of the pyran and cyclohexanone rings is 12.95 (6)°. In the crystal, molecules are linked via C—H⋯O hydrogen bonds, leading to chains running along [011].

Related literature

For the uses and biological importance of diketones, see: Bennett et al. (1999 ▶); Sato et al. (2008 ▶). For a related structure, see: Öztürk Yildirim et al. (2012) ▶.

Experimental

Crystal data

C₁₈H₁₅NO₃
M _r = 293.31
Triclinic,
a = 7.4426 (6) Å
b = 10.5117 (9) Å
c = 10.6887 (9) Å
α = 60.939 (4)°
β = 88.107 (5)°
γ = 77.546 (5)°
V = 711.22 (10) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.30 × 0.25 × 0.20 mm

Data collection

Bruker SMART APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T _min = 0.972, T _max = 0.982
10655 measured reflections
2949 independent reflections
2427 reflections with I > 2σ(I)
R _int = 0.031

Refinement

R[F ² > 2σ(F ²)] = 0.040
wR(F ²) = 0.118
S = 1.05
2949 reflections
201 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); 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 (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Supplementary Material

Click here for additional data file.^{(19.3KB, cif)}

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813001050/pv2617sup1.cif

e-69-0o254-sup1.cif^{(19.3KB, cif)}

Click here for additional data file.^{(141.8KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813001050/pv2617Isup2.hkl

e-69-0o254-Isup2.hkl^{(141.8KB, hkl)}

Click here for additional data file.^{(6KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813001050/pv2617Isup3.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
C15—H15⋯O2ⁱ	0.93	2.43	3.250 (2)	147

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank the TBI X-ray facility, CAS in Crystallography and Biophysics, University of Madras, India, for the data collection. TS also thanks the DST for an Inspire fellowship.

supplementary crystallographic information

Comment

Diketones are key intermediates in the preparation of various heterocyclic compounds (Sato et al., 2008) and are popular in organic synthesis for their applications in biology and medicine. They are known to exhibit antioxidant, antitumour and antibacterial activities (Bennett et al., 1999).

The bond distances and angles in the title compound (Fig. 1) agree very well with the corresponding bond distances and angles reported in a closely related compound (Öztürk Yildirim et al., 2012). The dihedral angle between the pyran ring (O3/C1/C2/C10/C11/C12) and the pyridine ring (N1/C2/C3/C4/C9/C10) is 3.08 (6)°. The dihedral angle between the pyran ring and the benzene ring (C11-C16) is 2.70 (6)°. Moreover, pyridine ring makes a diheral angle of 5.78 (6)° with the benzene ring (C11-C16). The dihedral angle between the pyran ring and the cyclohexanone ring is 12.95 (6)°. In the crystal, molecules are linked via C15–H15···O2 hydrogen bonding interactions leading to chains running along the b-axis (Table 1 & Fig. 2).

Experimental

2-Amino-4-oxo-4H-chromene-3-carbaldehyde (100 mg, 1.0 mmol) was reacted with 5,5-dimethylcyclohexane-1,3-dione (88 mg, 1.2 mmol) in the presence of yeterbium triflate (Yb(oft)3) (98 mg, 0.3 mmol) after stirring. All these reactants were dissolved in xylene (5 ml). The reaction mixture was refluxed at 398 K for 12 hours. The reaction mixture was extracted with ethyl acetate/hexane (40:60 v/v). The completion of the reaction was monitored by TLC. The end product was the title compound which was purified by column chromatography (ethyl acetate/hexane, 40:60), the yield being 80%. Single crystals suitable for X-ray diffraction were obtained by slow evaporation of a solution of the title compound in ethyl acetate at room temperature.