Molecular and Crystal Structure of 7,7-Dimethyl-2-pyridin-4-yl-6,7-dihydro-1,2,4-triazolo[1,5-a][1,3,5]triazin-5-amine [1]

doi:10.3390/cryst1030136

This article is

freely available
re-usable

Crystals 2011, 1(3), 136-144; doi:10.3390/cryst1030136

Article

Molecular and Crystal Structure of 7,7-Dimethyl-2-pyridin-4-yl-6,7-dihydro-1,2,4-triazolo[1,5-a][1,3,5]triazin-5-amine [1]

Anton V. Dolzhenko^1,* , Geok Kheng Tan², Lip Lin Koh², Anna V. Dolzhenko³ and Wai Keung Chui⁴

¹ School of Pharmacy, Faculty of Health Sciences, Curtin University of Technology, GPO Box U1987, Perth 6845, Western Australia, Australia ² Department of Chemistry, Faculty of Science, National University of Singapore, 3 Science Drive 3, Singapore 117543, Singapore ³ Perm State Pharmaceutical Academy, 2 Polevaya Street, Perm 614990, Russia ⁴ Department of Pharmacy, Faculty of Science, National University of Singapore, 18 Science Drive 4, Singapore 117543, Singapore

* Author to whom correspondence should be addressed.

Received: 13 July 2011; in revised form: 10 August 2011 / Accepted: 11 August 2011 / Published: 11 August 2011

Download PDF Full-Text [372 KB, uploaded 11 August 2011 15:44 CEST]

Abstract: When crystallized from ethanol, 7,7-dimethyl-2-pyridin-4-yl-6,7-dihydro-1,2,4-triazolo[1,5-a][1,3,5]triazin-5-amine forms crystals which have monoclinic (P2₁/n) symmetry with unit cell dimensions a = 7.3326(5) Å, b = 19.4897(14) Å, c = 8.6586(6) Å, α = 90°, β = 106.069(2)°, γ = 90°, V = 1189.06(14) Å³, Z = 4. The triazine ring in the molecule has a flattened boat conformation with gem-dimethyl groups as flagpole and bowsprit at the bow. The puckering parameters for the ring are: Q = 0.2996(14) Å, θ = 111.7(3)° and φ = 124.1(3)°. In the crystal, molecules are arranged in the three types of chains generated by the intermolecular NH···N hydrogen bonds. The extended chains with the C(11) graph-set motif running along a [010] axis are formed by the amino group hydrogen atom and the pyridine nitrogen atom of another molecule. The C(4)C(6) chains with the R²₂(8) binary graph-set motif running along a [101] direction are formed by linking the amino group hydrogen atom and the hydrogen atom at the triazine nitrogen atom with the triazole and triazine nitrogen atoms of another molecule, respectively. The centrosymmetric inverted dimers are formed via the C-H···π interactions between the methyl group hydrogen and the pyridine ring of the pair molecule.

Keywords: riazoles; triazines; 5-azapurines; hydrogen bonds; CH···π interactions

Supplementary Files

Supplementary File 1:
CIF-Document (CIF, 18 KB)

Article Statistics

Click here to load and display the download statistics.

Cite This Article

MDPI and ACS Style

Dolzhenko, A.V.; Tan, G.K.; Koh, L.L.; Dolzhenko, A.V.; Chui, W.K. Molecular and Crystal Structure of 7,7-Dimethyl-2-pyridin-4-yl-6,7-dihydro-1,2,4-triazolo[1,5-a][1,3,5]triazin-5-amine [1]. Crystals 2011, 1, 136-144.

AMA Style

Dolzhenko AV, Tan GK, Koh LL, Dolzhenko AV, Chui WK. Molecular and Crystal Structure of 7,7-Dimethyl-2-pyridin-4-yl-6,7-dihydro-1,2,4-triazolo[1,5-a][1,3,5]triazin-5-amine [1]. Crystals. 2011; 1(3):136-144.

Chicago/Turabian Style

Dolzhenko, Anton V.; Tan, Geok Kheng; Koh, Lip Lin; Dolzhenko, Anna V.; Chui, Wai Keung. 2011. "Molecular and Crystal Structure of 7,7-Dimethyl-2-pyridin-4-yl-6,7-dihydro-1,2,4-triazolo[1,5-a][1,3,5]triazin-5-amine [1]." Crystals 1, no. 3: 136-144.

Crystals EISSN 2073-4352 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert