Synthesis and X-ray structural investigations of 2-amino-7-methyl-4-(1-naphthyl)-5-oxo4H,5H-pyrano[4,3-b]pyran-3-carbonitrile and 2-amino-4-(1-naphthyl)-5-oxo-4H,5Hpyrano[3,2-c]chromene-3-carbonitrile
Synthesis and X-ray structural investigations of 2-amino-7-methyl-4-(1-naphthyl)-5-oxo4H,5H-pyrano[4,3-b]pyran-3-carbonitrile and 2-amino-4-(1-naphthyl)-5-oxo-4H,5Hpyrano[3,2-c]chromene-3-carbonitrile
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2-氨基-7-甲基-4-(1-萘基)-5-氧代4H,5H-吡喃并[4,3-b]吡喃-3-甲腈和2-氨基-4-的合成和X射线结构研究
DOI：
10.1007/s10870-005-5174-y
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发表时间：
2005
影响因子：
0.8
通讯作者：
L. Daniels
中科院分区：
文献类型：
--
作者：
V. Nesterov;David J. Wiedenfeld;S. Nesterova;L. Daniels
对两个标题化合物 C20H14N2O3 (4) 和 C23H14N2O3⋅C2H3N (5) 进行了合成和 X 射线结构研究。化合物 4 在单斜空间群 P21/n 中结晶，a = 7.0542(5)，b = 8.822(1)，c = 24.833(2) Å，β = 94.30(4)∘，V = 1541.0(4) Å3，Z = 4。化合物 5 用乙腈溶剂分子在单斜空间群P21/n，a = 11.075(1)，b = 7.854(1)，c = 22.703(2) Å，β = 90.67(1)∘，V = 1974.5(3) Å3，Z = 4。在这两个分子中，4H-吡喃环均采用扁平船构象。萘取代基占据假轴位置，与吡喃环平坦部分的二面角等于 4 中的 94.6(3) 和 5 中的 76.8(3)∘。这些片段的相互取向和杂环的平坦度导致 H⋅sH 分子内空间相互作用：4 和 2.11 中的 H4A⋅sH18A 1.98 Å 5 中的 Å。在 4 的晶体中，分子间氢键 N–H⋅sO 和 C–H⋅sN 将分子沿 b 轴连接成无限带。在 5 的晶体中，分子间氢键 N–H⋅sO 和 C–H⋅sN 将分子连接成平行于 bc 平面的无限层。在每种情况下，C–H⋅sN 相互作用都可以被认为是弱氢键。乙腈分子通过分子间弱 C–H⋅sN 氢键连接，沿 b 轴形成无限链。
Synthesis and X-ray structural investigations have been carried out for the two title compounds C20H14N2O3 (4) and C23H14N2O3⋅C2H3N (5). Compound 4 crystallizes in the monoclinic space group P21/n, with a = 7.0542(5), b = 8.822(1), c = 24.833(2) Å, β = 94.30(4)∘, V = 1541.0(4) Å3, and Z = 4. Compound 5 crystallizes with an acetonitrile solvent molecule in the monoclinic space group P21/n, with a = 11.075(1), b = 7.854(1), c = 22.703(2) Å, β = 90.67(1)∘, V = 1974.5(3) Å3, and Z = 4. In both molecules, the 4H-pyran ring adopts a flattened-boat conformation. The naphthalene substituent occupies a pseudo-axial position and the dihedral angle with the flat part of the pyran ring is equal to 94.6(3) in 4 and 76.8(3)∘ in 5. The mutual orientation of these fragments and the flatness of the heterocyclic rings lead to H⋅sH intramolecular steric interactions: H4A⋅sH18A 1.98 Å in 4 and 2.11 Å in 5. In the crystal of 4, intermolecular hydrogen bonds N–H⋅sO and C–H⋅sN link molecules into infinite tapes along the b axis. In the crystals of 5, intermolecular hydrogen bonds N–H⋅sO and C–H⋅sN link molecules into infinite layers parallel to the bc plane. In each case, the C–H⋅sN interaction can be considered to be a weak hydrogen bond. The acetonitrile molecules link via intermolecular weak C–H⋅sN hydrogen bonds to form infinite chains along the b axes.