Tert-Butyl 4-{[2-amino-4-(2-hydroxyphenyl)pyrimidin-5-yl]methyl}piperazine-1-carboxylate

Nilesh N Gajera,Edward R T Tiekink,Mukesh C Patel,Mukesh M Jotani

doi:10.1107/s1600536813025774

Nilesh N Gajera, Edward R T Tiekink + Show 2 more

Open Access

https://doi.org/10.1107/s1600536813025774

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Abstract

In the title compound, C20H27N5O3, the central piperazine ring adopts a chair conformation, with the N-bound carboxylate and methylene substituents occupying bisectional and equatorial orientations, respectively. A twist is evident between the aromatic rings [dihedral angle = 25.61 (9)°] but an intramolecular O—H⋯N hydrogen bond persists between these. Supramolecular tapes along [1-10] are formed in the crystal packing through N(amino)—H⋯O(hydroxyl) and N(amino)—H⋯N(pyrimidinyl) hydrogen bonds, and these are linked into layers in the ab plane by π–π interactions [inter-centroid distance between pyrimidinyl rings = 3.5919 (9) Å].

Highlights

In the title compound, C20H27N5O3, the central piperazine ring adopts a chair conformation, with the N-bound carboxylate and methylene substituents occupying bisectional and equatorial orientations, respectively
A twist is evident between the aromatic rings [dihedral angle = 25.61 (9) ] but an intramolecular O—H N hydrogen bond persists between these
N(amino)—H N(pyrimidinyl) hydrogen bonds, and these are linked into layers in the ab plane by – interactions

Summary

Data collection

V. Campus, Kadi, Gujarat, 382 715, India, bDepartment of Physics, Bhavan’s Sheth R. A. College of Science, Ahmedabad, Gujarat, 380 001, India, and cDepartment of Chemistry, University of Malaya, 50603. R factor = 0.050; wR factor = 0.141; data-to-parameter ratio = 18.8. C20H27N5O3, the central piperazine ring adopts a chair conformation, with the N-bound carboxylate and methylene substituents occupying bisectional and equatorial orientations, respectively. A twist is evident between the aromatic rings [dihedral angle = 25.61 (9) ] but an intramolecular O—H N hydrogen bond persists between these. N(amino)—H N(pyrimidinyl) hydrogen bonds, and these are linked into layers in the ab plane by – interactions [inter-centroid distance between pyrimidinyl rings =

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