Quinoline-2-carbaldehyde

William M Motswainyana; Martin O Onani

doi:10.1107/S1600536811035653

. 2011 Sep 14;67(Pt 10):o2573. doi: 10.1107/S1600536811035653

Quinoline-2-carbaldehyde

William M Motswainyana ^a, Martin O Onani ^a,^*

PMCID: PMC3201271 PMID: 22058739

Abstract

The title compound, C₁₀H₇NO, crystallizes with two almost planar molecules (A and B) in the asymmetric unit (r.m.s. deviations = 0.018 and 0.020 Å). In the crystal, the A molecules are linked by weak C—H⋯O interactions, thereby generating C(9) [001] chains. The B molecules do not exhibit any directional bonding interactions.

Related literature

For the synthesis of the title compound, see: Cooper & Cohen (1932 ▶). For its use in the synthesis of Schiff base ligands and imino-quinolyl-based transition metal complexes, see: Amandola & Mangano (2003 ▶); Prema & Wiznycia (2007 ▶); Ramos Silva et al. (2007 ▶); Ardizzoia et al. (2009 ▶). For its catalytic properties, see: Zhou et al. (2008 ▶).

Experimental

Crystal data

C₁₀H₇NO
M _r = 157.17
Monoclinic,
a = 7.0639 (7) Å
b = 21.564 (2) Å
c = 10.698 (1) Å
β = 107.884 (2)°
V = 1550.9 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 173 K
0.16 × 0.09 × 0.06 mm

Data collection

Bruker Kappa DUO APEXII diffractometer
17618 measured reflections
3887 independent reflections
2379 reflections with I > 2σ(I)
R _int = 0.055

Refinement

R[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 0.117
S = 1.00
3887 reflections
217 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); Atwood & Barbour, 2003 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811035653/hb6393sup1.cif

e-67-o2573-sup1.cif^{(18.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811035653/hb6393Isup2.hkl

e-67-o2573-Isup2.hkl^{(190.6KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811035653/hb6393Isup3.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
C4A—H4A⋯O1Aⁱ	0.95	2.53	3.424 (2)	158

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors acknowledge financial support from the NRF–Thuthuka division and the University of the Western Cape Senate Research.

supplementary crystallographic information

Comment

As part of our investigation of bimetallic complexes as catalysts for C—C coupling reactions, we attempted to synthesize palladium (II) complexes of a bis(imino-quinolyl) ligand. The binucleating ligand brings two metal centers into closer proximity and the resultant bimetallic complex possesses unique reactivity patterns and unusual catalytic properties (Zhou et al. 2008). In an attempt to prepare a bis(imino-quinolyl) palladium (II) complex, the title compound, (I), waas indavertantly obtained (Fig. 1). Dimensions are available in the archived CIF.

Experimental

Single crystals of 2-quinolinecarboxaldehyde were obtained as a result of the decomposition of bis(imino-quinolyl) chloromethyl palladium (II) complex. The bis-palladium (II) complex was prepared from the reaction of a bis(imino-quinolyl) ligand with 2 equimolar PdClMe(cod) in CH₂Cl₂. Orange needles of the title compound were grown by slow diffusion of hexane into the CH₂Cl₂ solution of the complex.