4,6-Dichloro-5-(2-meth­oxy­phen­oxy)-2,2′-bipyrimidine

Tian-tian Ren; Zhong Zhang; Cong-cong Zhong; Zhong-zhi Yang; Zhan-wang Shi

doi:10.1107/S160053681101419X

. 2011 May 7;67(Pt 6):o1334. doi: 10.1107/S160053681101419X

4,6-Dichloro-5-(2-methoxyphenoxy)-2,2′-bipyrimidine

Tian-tian Ren ^a, Zhong Zhang ^a, Cong-cong Zhong ^a, Zhong-zhi Yang ^a, Zhan-wang Shi ^a,^*

PMCID: PMC3120620 PMID: 21754730

Abstract

In the title compound, C₁₅H₁₀Cl₂N₄O₂, the dichloropyrimidine and methoxyphenoxy parts are approximately perpendicular [dihedral angle = 89.9 (9)°]. The dihedral angle between the two pyrimidine rings is 36.3 (4)° In the crystal, there are no hydrogen bonds but the molecules are held together by short intermolecular C⋯N [3.206 (3) Å] contacts and C—H⋯π interactions.

Related literature

For the use of 2,2′-bipyrimidine as a ligand in inorganic and organometallic chemistry, see: Fabrice et al. (2008 ▶); Hunziker & Ludi (1977 ▶). It was first synthesized by Bly and Mellon (1962 ▶) utilizing the Ullmann coupling of 2-bromopyrimidine in the presence of metallic copper.

Experimental

Crystal data

C₁₅H₁₀Cl₂N₄O₂
M _r = 349.17
Monoclinic,
a = 10.716 (2) Å
b = 8.1112 (18) Å
c = 18.601 (5) Å
β = 106.486 (3)°
V = 1550.3 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.43 mm⁻¹
T = 296 K
0.22 × 0.20 × 0.18 mm

Data collection

Siemens SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.911, T _max = 0.926
8106 measured reflections
2733 independent reflections
2319 reflections with I > 2σ(I)
R _int = 0.027

Refinement

R[F ² > 2σ(F ²)] = 0.042
wR(F ²) = 0.114
S = 1.08
2733 reflections
209 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.54 e Å⁻³

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAINT; 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 datablocks I, global. DOI: 10.1107/S160053681101419X/fl2331sup1.cif

e-67-o1334-sup1.cif^{(16.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053681101419X/fl2331Isup2.hkl

e-67-o1334-Isup2.hkl^{(134.2KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. C—H⋯π interactions (Å, °).

Cg is the centroid of the C9–C14 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯Cgⁱ	0.93	2.87	3.760 (3)	161

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors gratefully acknowledge financial support provided by the National Natural Science Foundation of China (20761002), the Natural Science Foundation of Guangxi (No. 0832080) and the Innovation Project of Guangxi University for Nationlities (No. gxun-chx2010080).

supplementary crystallographic information

Comment

2,2'-Bipyrimidine has been used as a ligand in inorganic and organometallic chemistry (Hunziker & Ludi, 1977; Fabrice et al., 2008) and exhibits remarkable stability in acidic medium. It was first synthesized by Bly and Mellon (1962) utilizing the Ullmann coupling of 2-bromopyrimidine in the presence of metallic copper. As part of our studies on the synthesis and characterization of these compounds, we report here the crystal structure of (I).

In (I) the dichloropyrimidine and the methoxyphenoxy are approximately perpendicular (dihedral angle of 89.90 (91) °). The dihedral angle between the two pyrimidine rings is 36.25 (38)° (Fig. 1).

The molecules are linked by intermolecular C—H···N , C—H···C and C···N short contacts. C12—H12···N4, C12···N4=3.639 (3), H12···N4=2.728 (3), and C12—H12···N4=166.49; C8···N2=3.206 (3); C1—H1···C12, C1···C12=3.725 (3), H1···C12=2.814 (3), and C1—H1···C12=166.14; C10—H10···C13, C10···C13=3.694 (3)), H10···C13=2.886 (3), and C13—H10···C10=146.05.

Experimental

A solution of 4,6-Dichloro-5-(2-methoxyphenoxy)-2,2'-bipyrimidine (10 mmol) in 50ml toluene was refluxed for 1h with stirring then filtered, washed several times with ethanol and dried in vacuo, to produce a powder of the title compound. The powder was added to 50ml toluene with stirring until completely dissolved. Finally, colourless crystals suitable for data collection were obtained by slow evaporation of the toluene at room temperature. Elemental analysis calculate: Elemental analysis: found: C, 51.60; H, 2.89; N, 16.05; calc. for C₁₅H₁₀Cl₂N₄O₂: C,51.53; H, 2.93; N, 16.11.