Crystal structure of ethyl 2-chloro-5,8-di­meth­oxy­quinoline-3-carboxyl­ate

Hasna Hayour; Abdelmalek Bouraiou; Sofiane Bouacida; Saida Benzerka; Ali Belfaitah

doi:10.1107/S1600536814017309

. 2014 Aug 1;70(Pt 9):o964–o965. doi: 10.1107/S1600536814017309

Crystal structure of ethyl 2-chloro-5,8-dimethoxyquinoline-3-carboxylate

Hasna Hayour ^a, Abdelmalek Bouraiou ^a, Sofiane Bouacida ^b,^c,^*, Saida Benzerka ^b, Ali Belfaitah ^a

PMCID: PMC4186085 PMID: 25309282

Abstract

In the title compound, C₁₄H₁₄ClNO₄, the dihedral angle between the quinoline ring system (r.m.s. deviation = 0.0142 Å) and ester planes is 18.99 (3)°. The C—O—C—C_m (m = methyl) torsion angle is −172.08 (10)°, indicating a trans conformation. In the crystal, the molecules are linked by C—H⋯O and C—H⋯N interactions, generating layers lying parallel to (101). Aromatic π-π stacking [centroid–centroid distances = 3.557 (2) and 3.703 (2)Å] links the layers into a three-dimensional network.

Keywords: crystal structure, quinoline derivatives, ester, hydrogen bonding, π–π stacking

Related literature

For the synthesis and applications of quinoline derivatives, see: Wang et al. (2011 ▶); Benzerka et al. (2012 ▶); Valdez et al. (2009 ▶). For our previous work, see: Bouraiou et al. (2012 ▶); Hayour et al. (2014 ▶); Benzerka et al. (2012 ▶).

Experimental

Crystal data

C₁₄H₁₄ClNO₄
M _r = 295.71
Triclinic,
a = 7.512 (4) Å
b = 9.759 (5) Å
c = 9.811 (5) Å
α = 76.071 (10)°
β = 72.021 (10)°
γ = 86.037 (10)°
V = 664.0 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.30 mm⁻¹
T = 150 K
0.25 × 0.14 × 0.12 mm

Data collection

Bruker APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2002 ▶) T _min = 0.690, T _max = 0.747
10769 measured reflections
5204 independent reflections
4090 reflections with I > 2σ(I)
R _int = 0.024

Refinement

R[F ² > 2σ(F ²)] = 0.036
wR(F ²) = 0.103
S = 1.04
5204 reflections
184 parameters
H-atom parameters constrained
Δρ_max = 0.5 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SIR2002 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and DIAMOND (Brandenburg & Berndt, 2001 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814017309/hg5402sup1.cif

e-70-0o964-sup1.cif^{(23.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814017309/hg5402Isup2.hkl

e-70-0o964-Isup2.hkl^{(249.7KB, hkl)}

Click here for additional data file.^{(5.4KB, cml)}

Supporting information file. DOI: 10.1107/S1600536814017309/hg5402Isup3.cml

Click here for additional data file.^{(1.8MB, tif)}

. DOI: 10.1107/S1600536814017309/hg5402fig1.tif

(Farrugia, 2012) the structure of the title compound with the atomic labelling scheme. Displacement are drawn at the 50% probability level.

Click here for additional data file.^{(1.3MB, tif)}

b . DOI: 10.1107/S1600536814017309/hg5402fig2.tif

(Brandenburg & Berndt, 2001) A diagram of the layered crystal packing of (I) viewed down the b axis and showing hydrogen bond [C—H⋯O in red and C—H⋯N in black] as dashed line.

CCDC reference: 1016211

Additional supporting information: crystallographic information; 3D view; checkCIF report

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10⋯O3ⁱ	0.93	2.56	3.482 (2)	173
C14—H14C⋯N1ⁱⁱ	0.96	2.61	3.476 (2)	150

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

Acknowledgments

We are grateful to all personnel of the PHYSYNOR Laboratory, Universite Constantine 1, Algeria, for their assistance. Thanks are due to the MESRS (Ministére de l’Enseignement Supérieur et de la Recherche Scientifique - Algérie) for financial support.

supplementary crystallographic information

S1. Comment

Quinolines have attracted considerable interest for many years due to their presence in the skeleton of a large number of bioactive compounds and natural products (Wang, et al. 2011), such as antibacterial (Benzerka, et al.2012). in going with our investigation, recently, we have reported the synthesis and structure determination of some new quinoline compounds (Hayour, et al., 2014; Bouraiou, et al. 2012). In this paper, we describe the synthesis and the structure determination of ethyl 2-chloro-5,8-dimethoxyquinoline-3-carboxylate (I) which obtained in one step, by addition of NaCN in presence of manganese dioxide in absolute ethanol to 2-chloro-5,8-dimethoxyquinoline-3-carbaldehyde. The molecular geometry and the atom-numbering scheme of (I) are shown in Fig. 1. In the asymmetric unit of title compound the quinoline ring is four time substituted by two methoxy, one chlore and one ethyl carboxylate. The two rings of quinolyl moiety are fused in an axial fashion and form dihedral angle of 1.75 (3) Å. The crystal packing can be described as double layers parallel to (101) plane, along the b axis (Fig. 2). It is stabilized by intermolecular hydrogen bond (N—H···O and C—H···O) and strong π–π stacking, resulting in the formation of infinite a three-dimensional network linking these layers together and reinforces cohesion of the structure (Fig. 2). Hydrogen-bonding parameters are listed in Table 1.

S2. Experimental

To a cold solution of NaCN (3 mmol) in absolute ethanol (15 mL), a mixture of 2-chloro-5,8-dimethoxy quinolin-3-carbaldehyde (1 mmol) and manganese dioxide (6.7 mmol) was added at 0°C, then the reaction mixture was stirred at 25°C during 3 h. After complexion, the title compound was obtained by simple filtration through a small column packed with 4 cm of celite and 3 cm of silica gel using CH₂Cl₂ as eluant (Valdez, et al. 2009).