Methyl 2-[2-(6-chloro­pyrimidin-4-yl­oxy)phen­yl]-3,3-dimethoxy­propanoate

Chao Sheng; Qing-Bing Xu; Yuan-Yuan Liu; Hong-Jun Zhu

doi:10.1107/S1600536809030736

. 2009 Aug 8;65(Pt 9):o2117. doi: 10.1107/S1600536809030736

Methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3,3-dimethoxypropanoate

Chao Sheng ^a, Qing-Bing Xu ^a, Yuan-Yuan Liu ^a, Hong-Jun Zhu ^a,^*

PMCID: PMC2970010 PMID: 21577532

Abstract

In the title compound, C₁₆H₁₇ClN₂O₅, the dihedral angle between the aromatic rings is 77.36 (4)°. An intramolecular C—H⋯O interaction results in the formation of a planar [r.m.s. deviation = 0.103 (2) Å] five-membered ring, which is oriented at a dihedral angle of 4.84 (4)° with respect to the adjacent benzene ring. In the crystal structure, weak intermolecular C—H⋯π interactions are found.

Related literature

For a related structure, see: Bowden & Brown (1996 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₆H₁₇ClN₂O₅
M _r = 352.77
Triclinic,
a = 9.5030 (19) Å
b = 10.051 (2) Å
c = 11.162 (2) Å
α = 101.24 (3)°
β = 108.47 (3)°
γ = 113.42 (3)°
V = 862.6 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 294 K
0.20 × 0.20 × 0.05 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ▶) T _min = 0.952, T _max = 0.988
3346 measured reflections
3140 independent reflections
1427 reflections with I > 2σ(I)
R _int = 0.035
3 standard reflections frequency: 120 min intensity decay: 1%

Refinement

R[F ² > 2σ(F ²)] = 0.078
wR(F ²) = 0.173
S = 1.07
3140 reflections
211 parameters
H-atom parameters constrained
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.45 e Å⁻³

Data collection: CAD-4 Software (Enraf–Nonius, 1985 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809030736/hk2749sup1.cif

e-65-o2117-sup1.cif^{(19.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809030736/hk2749Isup2.hkl

e-65-o2117-Isup2.hkl^{(154KB, 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⋯O5	0.98	2.25	2.777 (6)	113
C1—H1B⋯Cg2ⁱ	0.96	2.97	3.696 (5)	134
C16—H16A⋯Cg1ⁱ	0.93	2.85	3.661 (4)	146

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Symmetry code: (i) Inline graphic . Cg1 and Cg2 are centroids of the C7–C12 and N1/N2/C13–C16 rings, respectively.

Acknowledgments

The authors thank the Center of Testing and Analysis, Nanjing University, for support.

supplementary crystallographic information

Comment

The title compound can be used as an intermediate in the preparation of azoxystrobin, which is an important fungicide (Bowden & Brown, 1996). We report herein the crystal structure of the title compound, which is of interest to us in the field.

In the molecule of the title compound (Fig. 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. Rings A (C7-C12) and B (N1/N2/C13-C16) are, of course, planar and the dihedral angle between them is A/B = 77.36 (4)°. Intramolecular C-H···O interaction (Table 1) results in the formation of a planar five-membered ring C (O5/C6-C8/H6A), which is oriented with respect to the adjacent ring A at a dihedral angle of A/C = 4.84 (4)°.

In the crystal structure, weak C—H···π interactions (Table 1) are found.

Experimental

The title compound was prepared acording to a literature method (Bowden & Brown, 1996). Crystals suitable for X-ray analysis were obtained by dissolving the title compound in methanol and evaporating the solvent slowly at room temperature for 8 d.