Methyl 4,6-dichloro­pyridine-3-carboxyl­ate

Yi Ma; Jun Liu

doi:10.1107/S1600536808011914

. 2008 May 3;64(Pt 6):o995. doi: 10.1107/S1600536808011914

Methyl 4,6-dichloropyridine-3-carboxylate

Yi Ma ^a,^*, Jun Liu ^b

PMCID: PMC2961487 PMID: 21202720

Abstract

The title compound, C₇H₅Cl₂NO₂, crystallizes with two independent molecules in the asymmetric unit. The bond lengths and angles in both molecules are within normal ranges. In the crystal structure, weak intermolecular C—H⋯O hydrogen bonds link the molecules into layers parallel to the [010] plane.

Related literature

For details of the biological activity of the title compound, see: Wallace et al. (2006 ▶); Bondinell et al. (2002 ▶). For a related structure, see: McArdle et al. (1982 ▶).

Experimental

Crystal data

C₇H₅Cl₂NO₂
M _r = 206.02
Monoclinic,
a = 8.033 (4) Å
b = 18.974 (9) Å
c = 11.240 (6) Å
β = 95.224 (8)°
V = 1705.9 (15) Å³
Z = 8
Mo Kα radiation
μ = 0.71 mm⁻¹
T = 298 (2) K
0.45 × 0.19 × 0.06 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T _min = 0.739, T _max = 0.958
8532 measured reflections
3012 independent reflections
2289 reflections with I > 2σ(I)
R _int = 0.035

Refinement

R[F ² > 2σ(F ²)] = 0.052
wR(F ²) = 0.135
S = 1.08
3012 reflections
217 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and local programs.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808011914/hg2396sup1.cif

e-64-0o995-sup1.cif^{(17.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808011914/hg2396Isup2.hkl

e-64-0o995-Isup2.hkl^{(147.8KB, 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
C6—H6A⋯O3ⁱ	0.93	2.41	3.309 (4)	162
C11—H11A⋯O2ⁱⁱ	0.93	2.60	3.513 (4)	168

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

supplementary crystallographic information

Comment

Methyl 4,6-dichloropyridine-3-carboxylate is a useful intermediate for the synthesis of different kinase inhibitors (Wallace et al., 2006; Bondinell et al., 2002). In this paper, we report the crystal structure of the title compound (I).

Compound (I) crystallizes with two independent molecules in the asymmetric unit (Fig. 1), all bond lengths and angles are normal and in a good agreement with those reported previously (McArdle et al., 1982). The dihedral angles between the planes of the methoxycarbonyl group (C1/C2/O1/O2; C8/C9/O3/O4) and pyridine rings in the two independent molecules are 10.9 (2) and 8.1 (4)°. In the crystal structure, weak intermolecular C—H···O hydrogen bonds link the molecules into layers parallel to the b axis.

Experimental

Methyl 4, 6-dichloropyridine-3-carboxylate was synthesized from Methyl 4, 6-dihydroxypyridine-3-carboxylate via chlorination with POCl₃. The desired compound was obtained as a low melting yellow solid in 89% yield. Crystals suitable for X-ray diffraction analysis were obtained by slow evaporation of a solution in a hexane/dichloromethane mixture (1: 4 v/v) at room temperature over a period of one week.