4-Methyl-6-phenyl­pyrimidin-2-amine

Zhen-Jiang Li; Jun-E Huang; A-Lan Meng

doi:10.1107/S1600536808008003

. 2008 Mar 29;64(Pt 4):o759. doi: 10.1107/S1600536808008003

4-Methyl-6-phenylpyrimidin-2-amine

Zhen-Jiang Li ^a,^*, Jun-E Huang ^a, A-Lan Meng ^a

PMCID: PMC2960917 PMID: 21202148

Abstract

The title compound, C₁₁H₁₁N₃, was synthesized as part of our research into functionalized pyrimidines. It crystallizes with two independent molecules in the asymmetric unit that differ only in the twist between the two aromatic rings; the torsion angles between the rings are 29.9 (2) and 45.1 (2)°. The crystal packing is dominated by intermolecular N—H⋯N hydrogen bonds between independent and equivalent molecules, forming an infinite three-dimensional network.

Related literature

For biological activity, see: Zhu & Yang (2005 ▶); Sherrington & Taskinen (2001 ▶); Ligthart et al. (2005 ▶). For a similar structure, see: Fun et al. (2006 ▶).

Experimental

Crystal data

C₁₁H₁₁N₃
M _r = 185.23
Monoclinic,
a = 14.0558 (11) Å
b = 9.3808 (7) Å
c = 18.5227 (12) Å
β = 125.950 (4)°
V = 1977.1 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 273 (2) K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART 1K CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T _min = 0.977, T _max = 0.985
17472 measured reflections
3619 independent reflections
2760 reflections with I > 2σ(I)
R _int = 0.033

Refinement

R[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 0.113
S = 1.04
3619 reflections
256 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SMART; data reduction: SAINT (Bruker, 2001 ▶); 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 h-1, I. DOI: 10.1107/S1600536808008003/fl2182sup1.cif

e-64-0o759-sup1.cif^{(20.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808008003/fl2182Isup2.hkl

e-64-0o759-Isup2.hkl^{(177.5KB, 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
N1—H1A⋯N3ⁱ	0.86	2.38	3.1918 (18)	157
N1—H1B⋯N6ⁱ	0.86	2.35	3.2095 (18)	175
N4—H4C⋯N2ⁱ	0.86	2.29	3.1474 (19)	176
N4—H4B⋯N5ⁱⁱ	0.86	2.24	3.0834 (18)	166

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

Acknowledgments

The authors thank the Natural Science Foundation of Shandong Province (grant No. Y2005F08).

supplementary crystallographic information

Comment

Pyrimidines are broadly used in the preparation of pesticides and medications (Zhu & Yang, 2005). Functionalized pyrimidines are important for the synthesis of purine- and pteridine-related compounds and also for multiple hydrogen-bonding interactions that play a role in molecular recognition and supramolecular chemistry (Sherrington & Taskinen, 2001; Ligthart et al., 2005). In the title compound, (I), (fig. 1) there are two molecules per asymmetric unit that differ only in the twist between the two aromatic rings with dihedral angles between the phenyl and pyrimidine rings of 29.41 (2)° 46.32 (3)°. Bond lengths and angles for (I) are generally normal (Fun et al., 2006).

In the packing there are intermolecular N—H···N hydrogen bonds that link each independent molecule to related self molecules as well as to the second molecule in the asymmetric unit to create an infinite network of hydrogen bonded molecules (Table 1, Fig. 2).

Experimental

The single crystals of the title compound were obtained by reaction of 1-phenylbutane-1,3-dione(0.2 mmol) with guanidine nitrate(0.2 mmol) by refluxing in DMF(50 ml). The product (yied 89%) was stirred in the DMF and single crystals of the title compound suitable for X-ray measurements were obtained by recrystallization from DMF at room temperature.