N-(Quinolin-8-yl)quinoline-2-carbox­amide

Yanfeng Li; Hongbo Zhou; Xiaoping Shen

doi:10.1107/S1600536812020144

. 2012 May 12;68(Pt 6):o1688. doi: 10.1107/S1600536812020144

N-(Quinolin-8-yl)quinoline-2-carboxamide

Yanfeng Li ^a, Hongbo Zhou ^a, Xiaoping Shen ^a,^*

PMCID: PMC3379284 PMID: 22719482

Abstract

In the title compound, C₁₉H₁₃N₃O, the dihedral angle between the two quinoline systems is 11.54 (3)°. The molecular conformation is stabilized by intramolecular N—H⋯N and C—H⋯O hydrogen bonds, with N—H⋯N being bifurcated towards the two N atoms of the two quinoline rings. In the crystal, there are weak intermolecular π–π interactions present involving the quinoline rings [centroid–centroid distance 3.7351 (14) Å].

Related literature

For the synthesis of the title compound and related structures, see: Kim et al. (2009 ▶). For applications of the title compound and background to the synthesis, see: Wang et al. (2011 ▶).

Experimental

Crystal data

C₁₉H₁₃N₃O
M _r = 299.32
Orthorhombic,
a = 6.3651 (13) Å
b = 11.475 (2) Å
c = 19.861 (4) Å
V = 1450.6 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 173 K
0.25 × 0.15 × 0.15 mm

Data collection

Rigaku Saturn 724 CCD diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T _min = 0.978, T _max = 0.987
6769 measured reflections
1553 independent reflections
1442 reflections with I > 2σ(I)
R _int = 0.036

Refinement

R[F ² > 2σ(F ²)] = 0.035
wR(F ²) = 0.082
S = 1.06
1553 reflections
208 parameters
H-atom parameters constrained
Δρ_max = 0.10 e Å⁻³
Δρ_min = −0.13 e Å⁻³

Data collection: CrystalClear (Rigaku, 2008 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812020144/zl2476sup1.cif

e-68-o1688-sup1.cif^{(20.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812020144/zl2476Isup2.hkl

e-68-o1688-Isup2.hkl^{(76.6KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812020144/zl2476Isup3.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
N2—H2A⋯N1	0.88	2.27	2.693 (2)	109
N2—H2A⋯N3	0.88	2.27	2.684 (2)	109
C12—H12⋯O1	0.95	2.25	2.867 (2)	122

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Acknowledgments

The authors thank the National Natural Science Foundation of China for financial support (grant No. 51072071).

supplementary crystallographic information

Comment

The title compound (Hqcq) can act as a tridentate ligand, and has been incorporated into the cyanometalate building block [Fe(qcq)(CN)₃]^- {qcq = 8-(2-quinolinecarboxamido)quinoline anion}, in which the Fe^III ion is coordinated by three carbon atoms of cyanide groups and three N-donors from the qcq ligand in a mer-arrangement (Kim et al., 2009). Through replacement of the cyanide ligands the Fe(qcq) fragment can coordinate to transition metal ions to form various polynuclear and one-dimensional structures with fascinating magnetic properties such as single molecular magnets and single-chain magnets (Kim et al., 2009; Wang et al., 2011). Herein, the crystal structure of the tridentate ligand of Hqcq is presented.

The molecular structure of the title compound is shown in Fig. 1. The quinoline rings are essentially planar, with a maximum deviation of 0.046 (1) Å for atom C8 in the (N1/C1-C9) ring and 0.016 (1) Å for atom C14 in the (N3/C11-C19) ring. The dihedral angle between the two quinoline rings is 11.54 (3)°. The amide (N2/C10/O1) plane forms dihedral angles of 14.1 (1)° and 4.2 (1)° with the quinoline rings of (N1/C1-C9) and (N3/C11-C19), respectively. The bond lengths of the title molecule are slightly different from those reported for [Fe(qcq)(CN)₃]^- (Kim et al., 2009), probably owing to the coordination effect to the tridentate ligand. There are intramolecular hydrogen-bonding interactions between the amido N atom and the N atoms of the quinoline rings, and between the O atom of amide group and the C atom of the quinoline ring. The amido N atom (N2) forms bifurcated hydrogen bonds towards the two N atoms (N1, N3) of the two quinoline rings (Table 1).

In the crystal structure, no significant intermolecular hydrogen bonds are observed. The crystal structure features intermolecular π-π interactions between different types of quinoline rings with a distance of ca. 3.735 Å between the centroids of the respective rings (Fig. 2), and the adjacent rings tilted against each other.

Experimental

The compound of 8-(2-quinolinecarboxamido)quinoline (Hqcq) was preparecd according to a literature method (Kim et al., 2009). Then, 0.3 mmol of Hqcq was added to MeCN (20 mL) with stirring. The resulting solution was filtered and the filtrate was left for slow evaporation in the dark at room temperature. Yellow block-shaped crystals of the title compound suitable for single-crystal X-ray diffraction were obtained after two weeks. Melting point = 429.6-430.5 K. IR (KBr, cm^-1): 3314(s), 3044(m), 1678(vs), 1523(vs), 1488(s), 1427(s), 1325(s), 1126(m), 913(s), 834(s), 764(vs), 611(m), 588(m).