Document Type

Article

Publication Date

Fall 9-18-2007

Abstract

The synthesis of heterocyclic thioureas from heterocyclic amines with phenyl- or methylisothiocyanate or CS2 is described. Seven new X-ray crystal structures are reported: In N-(3-pyridyl)-N'-phenylthiourea (Pna2(1), a = 10.1453(3), b = 17.6183(5), c = 6.4787(2), V = 1158.02(6), Z = 4) hydrogen-bonding results in formation of a 3D network consisting of helices, which form channels parallel to the c-axis. In N-(4-pyridyl)-N'-phenylthiourea (P2(1)/c, a = 16.9314(3), b = 10.3554(2), c = 13.5152(3), beta= 106.5080(10), V = 2271.96(8), Z = 4, two independent molecules) hydrogen-bonding results in N-H center dot center dot center dot S bridged dimers and N-H center dot center dot center dot Py chains, forming a 2D sheet network. In N-(2-pyrimidyl)-N'-phenylthiourea (P2(1)/c, a = 5.45900(10), b = 13.8559(2), c = 14.3356(3), beta= 94.9800(10), V = 1080.24(3), Z = 4) and N-(2-pyrimidyl)-N'-methylthiourea (P2(1)/c, a = 8.8159(5), b = 11.2386(5), c = 7.7156(4), beta= 95.629(2), V = 760.76(7), Z = 4) pairs of intra- and intermolecular N-H center dot center dot center dot N interactions produce dimers. Dimer formation through N-H center dot center dot center dot S occurs for N-(2-thiazolyl)-N'-methylthiourea (C2/c, a = 17.9308(3), b = 7.78260(10), c = 10.8686(2), beta= 105.3740(10), V = 1462.42(4), Z = 8). Two symmetrically disubstituted thioureas were examined: N,N'-bis(2-pyridyl)thiourea (Fdd2, a = 15.1859(2), b = 30.1654(3), c = 9.44130(10), V = 4324.95(8), Z = 16) forms intra- and intermolecular N-H center dot center dot center dot Py hydrogen-bonds, forming a 1D zigzag chain and N,N'-bis(3-pyridyl)thiourea (P2(1)/c, a = 13.2461(2), b = 6.26170(10), c = 12.3503(2), beta= 96.0160(10), V = 1018.73(3), Z = 4) forms intermolecular N-H center dot center dot center dot Py hydrogen-bonds, resulting in 2D sheets.

Journal Title

JOURNAL OF CHEMICAL CRYSTALLOGRAPHY

DOI

10.1007/s10870-007-9246-1

Volume

37

Issue

11

First Page

755

Publisher Statement

This is a post-peer-review, pre-copyedit version of an article published in Journal of Chemical Crystallography. The final authenticated version is available online at: 10.1007/s10870-007-9246-1.

Share

COinS