Marciniak Bernard, Rozycka-Sokolowska Ewa
Institute of Chemistry and Environmental Protection, Jan Dlugosz University, al. Armii Krajowej 13/15, 42-200 Czestochowa, Poland.
Acta Crystallogr C. 2009 Dec;65(Pt 12):o630-4. doi: 10.1107/S0108270109047556. Epub 2009 Nov 18.
The structure of 4-methoxy-1-naphthol, C(11)H(10)O(2), (I), contains an intermolecular O-H...O hydrogen bond which links the molecules into a simple C(2) chain running parallel to the shortest crystallographic b axis. This chain is reinforced by intermolecular pi-pi stacking interactions. Comparisons are drawn between the crystal structure of (I) and those of several of its simple analogues, including 1-naphthol and some monosubstituted derivatives, and that of its isomer 7-methoxy-2-naphthol. This comparison shows a close similarity in the packing of the molecules of its simple analogues that form pi-stacks along the shortest crystallographic axes. A substantial spatial overlap is observed between adjacent molecules in such stacks. In this group of monosubstituted naphthols, the overlap depends mainly on the position of the substituents carried by the naphthalene moiety, and the extent of the overlap depends on the substituent type. By contrast with (I), in the crystal structure of the isomeric 7-methoxy-2-naphthol there are no O-H...O hydrogen bonds or pi-pi stacking interactions, and sheets are formed by O-H...pi and C-H...pi interactions.
4-甲氧基-1-萘酚（C₁₁H₁₀O₂，(I)）的结构包含一个分子间O-H...O氢键，该氢键将分子连接成一条平行于最短晶体学b轴的简单C₂链。这条链通过分子间π-π堆积相互作用得到加强。对(I)的晶体结构与其几种简单类似物（包括1-萘酚和一些单取代衍生物）以及其异构体7-甲氧基-2-萘酚的晶体结构进行了比较。这种比较表明，其简单类似物的分子堆积沿着最短晶体学轴形成π-堆积，具有密切的相似性。在这种堆积中，相邻分子之间观察到大量的空间重叠。在这组单取代萘酚中，重叠主要取决于萘部分所携带取代基的位置，重叠程度取决于取代基类型。与(I)相反，在异构体7-甲氧基-2-萘酚的晶体结构中，不存在O-H...O氢键或π-π堆积相互作用，而是通过O-H...π和C-H...π相互作用形成片层。
