4-(4-Fluoro­phen­yl)-2-oxo-1,2,5,6-tetra­hydro­benzo[h]quinoline-3-carbonitrile

Jinpeng Zhang; Jie Ding; Shu Yan; Liangce Rong; Lichun Xu

doi:10.1107/S1600536809017991

. 2009 May 20;65(Pt 6):o1354. doi: 10.1107/S1600536809017991

4-(4-Fluorophenyl)-2-oxo-1,2,5,6-tetrahydrobenzo[h]quinoline-3-carbonitrile

Jinpeng Zhang ^a, Jie Ding ^b, Shu Yan ^b, Liangce Rong ^b, Lichun Xu ^a,^*

PMCID: PMC2969758 PMID: 21583205

Abstract

In the molecule of the title compound, C₂₀H₁₃FN₂O, the fluorophenyl ring is oriented at a dihedral angle of 72.76 (3)° with respect to the fused benzene ring. In the crystal structure, intermolecular N—H⋯O, C—H⋯O and C—H⋯F interactions link the molecules into chains. π–π contacts between the quinoline and benzene rings [centroid–centroid distance = 3.918 (3) Å] may further stabilize the structure. A weak C—H⋯π interaction is also present. The O atom and two of the CH₂ groups of the quinoline ring system are disordered over two positions. The O atom was refined with occupancies of 0.489 (17) and 0.511 (17), while C and H atoms were refined with occupancies of 0.435 (13) and 0.565 (13).

Related literature

For general background to substituted six-membered lactams, see: Daly (1998 ▶); Plunkett (1994 ▶); Robertson et al. (1986 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₂₀H₁₃FN₂O
M _r = 316.32
Triclinic,
a = 8.116 (10) Å
b = 9.278 (12) Å
c = 11.263 (14) Å
α = 98.674 (19)°
β = 105.095 (17)°
γ = 104.846 (18)°
V = 769.7 (16) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.48 × 0.35 × 0.33 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.956, T _max = 0.970
3950 measured reflections
2656 independent reflections
1399 reflections with I > 2σ(I)
R _int = 0.020

Refinement

R[F ² > 2σ(F ²)] = 0.048
wR(F ²) = 0.144
S = 1.00
2656 reflections
240 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); 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 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809017991/hk2684sup1.cif

e-65-o1354-sup1.cif^{(18.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809017991/hk2684Isup2.hkl

e-65-o1354-Isup2.hkl^{(130.4KB, 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
N1—H1⋯O1ⁱ	0.86	2.08	2.883 (3)	155
C7—H7⋯O1ⁱ	0.93	2.35	3.223 (3)	157
C12—H12B⋯O1ⁱⁱ	0.97	2.21	2.863 (3)	124
C13—H13B⋯F1ⁱⁱⁱ	0.97	2.42	3.270 (3)	147
C15—H15⋯Cg3^iv	0.93	2.90	3.671 (3)	141

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

Acknowledgments

The authors thank the National Natural Science Foundation of China (grant No. 30872143) and the Foundation of Xuzhou Medical College (grant No. 08 K J50) for financial support.

supplementary crystallographic information

Comment

Substituted six-membered lactams have attracted the attention of synthetic organic chemists for many years because these structural features are found in a wide variety of naturally occurring alkaloids (Daly, 1998; Plunkett, 1994). Since compounds with these scaffolds have been shown to exhibit significant pharmacological properties, medicinal chemists often incorporate these motifs in the design of novel biologically active molecules. For example, compounds Arnrinone 1 and Milrinone 2 are the cardiotonic drugs (Robertson et al., 1986) and that have been found to display effective activities on therapy of miocardial infarction. Development of a general and efficient synthetic strategy to synthesize those compounds is still desired. We report herein the crystal structure of the title compound.

In the molecule of the title compound (Fig. 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. Rings A (N1/C1-C5), C (C6-C11) and D (C14-C19) are, of course, planar and they are oriented at dihedral angles of A/C = 3.57 (3), A/D = 76.11 (3) and C/D = 72.76 (3) °. Ring B (C4-C6/C11-C13) is not planar, and adopts twisted conformation.

In the crystal structure, intermolecular N-H···O, C-H···O and C-H···F interactions (Table 1) link the molecules into chains (Fig. 2), in which they may be effective in the stabilization of the structure. The π···π contact between the quinoline and the benzene rings, Cg1—Cg3ⁱ [symmetry code: (i) 1 - x, -y, 1 - z, where Cg1 and Cg3 are centroids of the rings A (N1/C1-C5) and C (C6-C11), respectively] may further stabilize the structure, with centroid-centroid distance of 3.918 (3) Å. There also exists a weak C-H···π interaction (Table 1).

Experimental

The title compound was prepared by the reaction of 3,4-dihydronaphthalen-1(2H) -one (2 mmol), aromatic aldehydes (2 mmol), malononitrile (3 mmol) and NaOH (2 mmol) under solvent-free conditions using heating method.