N-Cyclo­hexyl-N-{[3-(4,6-dimeth­oxy­pyrimidin-2-yl­oxy)pyridin-2-yl]meth­yl}4,6-dimeth­oxy­pyrimidin-2-amine

De-Cai Wang; Yu-Jing Wang; Jun-Song Song; Ping Wei; Ping-Kai Ou-yang

doi:10.1107/S1600536812013104

. 2012 Mar 31;68(Pt 4):o1272. doi: 10.1107/S1600536812013104

N-Cyclohexyl-N-{[3-(4,6-dimethoxypyrimidin-2-yloxy)pyridin-2-yl]methyl}4,6-dimethoxypyrimidin-2-amine

De-Cai Wang ^a,^*, Yu-Jing Wang ^a, Jun-Song Song ^a, Ping Wei ^a, Ping-Kai Ou-yang ^a

PMCID: PMC3344196 PMID: 22606199

Abstract

In the title compound, C₂₄H₃₀N₆O₅, the cyclohexyl ring adopts a chair conformation, while the remainder of the molecule adopts a U-shape. The dihedral angles between the pyridine ring and the pendant pyrimidine rings are 69.04 (12) and 75.99 (9)°. The two pyrimidine rings, however, are nearly parallel to one another, with a dihedral angle of 8.56 (15)° between them. They are also involved in an intramolecular π–π stacking interaction with a distance of 3.6627 (18) Å between the ring centroids. In the crystal, C—H⋯O contacts link the molecules into chains along the b axis.

Related literature

For the synthesis and applications of the title compound, see: Yang & Lu (2010 ▶).

Experimental

Crystal data

C₂₄H₃₀N₆O₅
M _r = 482.54
Triclinic,
a = 7.0260 (14) Å
b = 10.624 (2) Å
c = 17.084 (3) Å
α = 72.95 (3)°
β = 84.18 (3)°
γ = 79.56 (3)°
V = 1197.4 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.972, T _max = 0.991
4410 measured reflections
4410 independent reflections
2478 reflections with I > 2σ(I)
R _int = 0.000
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F ² > 2σ(F ²)] = 0.063
wR(F ²) = 0.178
S = 1.00
4410 reflections
316 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; 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.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812013104/sj5221sup1.cif

e-68-o1272-sup1.cif^{(25KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812013104/sj5221Isup2.hkl

e-68-o1272-Isup2.hkl^{(216KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812013104/sj5221Isup3.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
C18—H18B⋯O3ⁱ	0.96	2.69	3.477 (4)	140

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Symmetry code: (i) Inline graphic .

Acknowledgments

The work was supported by the Center for Testing and Analysis, Nanjing University.

supplementary crystallographic information

Comment

The title compound is an important organic intermediate for the synthesis of pyrimidine-oxy-N-aryl benzyl amine derivatives, important compounds for use as new pesticides Yang & Lu (2010). In the process of synthesizing one such derivative, we obtained crystals of the intermediate and we report its crystal structure herein.

As shown in Fig.1, the cyclohexyl ring(C19—C24) adopts a chair conformation, while the remainder of the molecule is U shaped. The dihedral angles between the central pyridyl ring(C1—C5/N1) and the pendant pyrimidine rings (C6—C9/N2/N3 and C13—C16/N5/N6) are 69.04 (12) and 75.99 (9)°, respectively. The the two pyrimidine rings are nearly parallel to each other, with a dihedral angle of 8.56 (15)° between them. An intramolecular π-π stacking interaction also occurs with a distance of 3.6627 (18)Å between the (C6—C9/N2/N3) and (C13—C16/N5/N6) ring centroids. In the crystal, molecules are linked by weak C18—H18B···O hydrogen-bonds forming chains along b.

Experimental

The title compound was synthesized according to a published procedure (Yang & Lu, 2010). The product (0.3 g) was crystallized in methanol (15ml) at room temperature to give colorless crystals that were used for data collection.