The title compound, 1,5,9,13-tetraazacyclohexadecane (I), has been prepared in 60% yield on both a 0.01- and a 0.2-mol scale by the condensation of the ditosylate of 1,3-propanediol with the disodium salt of N,N',N'',N'''-tetra-p-toluene-sulfonyl-N,N'-bis(3-aminopropyl)-1,3-propanediamine, followed by the removal of the tosylate groups in 98% sulfuric acid. The crystal structure of I was determined from x-ray diffraction data collected by countermethods. The overall symmetry of the molecule, excluding the nitrogen hydrogen atoms is D/sub 2d/. That the amine hydrogens on adjacent nitrogens are trans lowers the molecular symmetry to S/sub 4/, which is obeyed within experimental error. The four nitrogens form a square with an average edge length of 2.925 (4) A. The trimethylene groups are in chair configurations with adjacent groups folding toward opposite sides of the nitrogen plane. Refinement on F/sup 2/ using all 1866 measured independent reflections by full-matrix least-squares led to an R factor of 6.6%. Unit cell dimensions in the space group P2/sub 1//n are a = 12.764 (6), b = 12.201 (6), c = 9.579 (4) A; ..beta.. = 108.13 (3)/sup 0/; and the calculated density is 1.07 g cm/sup -3/ for z = 4. 3 tables, 4 figures, 64 references.

中文翻译：

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1,5,9,13-四氮杂环十六烷（[16]aneN4）的高产合成及晶体结构

标题化合物 1,5,9,13-四氮杂环十六烷 (I) 通过 1,3-丙二醇的二甲苯磺酸酯与二钠缩合，以 0.01- 和 0.2-mol 的规模以 60% 的收率制备N,N',N'',N'''-四对甲苯磺酰基-N,N'-双(3-氨基丙基)-1,3-丙二胺的盐，然后去除甲苯磺酸酯基团在 98% 的硫酸中。I 的晶体结构是由反方法收集的 X 射线衍射数据确定的。除氮氢原子外，分子的整体对称性为 D/sub 2d/。相邻氮原子上的胺氢是反式将分子对称性降低到 S/sub 4/，这是在实验误差内遵守的。四个氮形成一个正方形，平均边长为 2.925 (4) A。三亚甲基呈椅式结构，相邻基团向氮平面的相对侧折叠。通过全矩阵最小二乘法使用所有 1866 次测量的独立反射对 F/sup 2/ 进行细化，导致 R 因子为 6.6%。空间群 P2/sub 1//n 中的晶胞维数为 a = 12.764 (6), b = 12.201 (6), c = 9.579 (4) A；..beta.. = 108.13 (3)/sup 0/; 并且计算的密度为 1.07 g cm/sup -3/ for z = 4。3 个表格，4 个数字，64 个参考文献。