Synthesis and Crystal Structure of 5-[2-(6-bromonaphthalenyloxymethyl)]-3-(4-morpholinomethyl)-1,3,4-oxadiazole-2(3H)-thione
Synthesis and Crystal Structure of 5-[2-(6-bromonaphthalenyloxymethyl)]-3-(4-morpholinomethyl)-1,3,4-oxadiazole-2(3H)-thione
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5-[2-(6-溴萘氧基甲基)]-3-(4-吗啉代甲基)-1,3,4-恶二唑-2(3H)-硫酮的合成及晶体结构
DOI：
10.1007/s10870-009-9570-8
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发表时间：
2009
影响因子：
0.8
通讯作者：
B. Sarojini
中科院分区：
文献类型：
--
作者：
J. Jasinski;R. Butcher;A. N. Mayekar;H. Yathirajan;B. Narayana;B. Sarojini
标题化合物 C18H18BrN3O3S，1,3,4-恶二唑的衍生物，在三斜空间群 P-1 中结晶，晶胞参数 a = 6.8731(3)、b = 8.9994(4)、c = 15.7099(6) Å、α = 92.779(3)°， β=130.575(3)°，γ=107.868(4)°，Z=2。平面萘环和吗啉(椅)环与平面恶二唑环的平均平面之间的二面角分别为50.1(8)和76.8(6)°。平面萘环与吗啉环的平均平面扭转52.2(5)°。在晶胞中紧密堆积的萘基、吗啉和羟甲基的溴原子和氢原子之间观察到一组四个分子间紧密接触。这些分子相互作用与萘基团的两个 6 元环的重心之间发生的一系列额外的 π-π 堆积相互作用相结合，影响这三个基团中每一个的扭转角。 MOPAC AM1 计算晶体结构的构象能 [226.0128(9) kcal] 与几何优化后的最小能量结构 [29.9744(1) kcal] 相比，发现值显着降低。 AM1计算后，上述三组扭转角也发生变化，这支持了分子间C–H·Br短程相互作用和Cg π–π堆积相互作用对这些角度的影响，从而起到稳定晶体堆积的作用。图解摘要晶体结构报道了 5-{[(6-溴萘-2-基)氧基]甲基}-3-(吗啉-4-基甲基)-1,3,4-恶二唑-2(3H)-硫酮，C18H18BrN3O3S，描述了其几何和堆积参数，并与 MOPAC 计算计算进行了比较。
The title compound, C18H18BrN3O3S, a derivative of 1,3,4-oxadiazole, crystallizes in the triclinic space group P-1 with unit cell parameters a = 6.8731(3), b = 8.9994(4), c = 15.7099(6) Å, α = 92.779(3)°, β = 130.575(3)°, γ = 107.868(4)°, Z = 2. The dihedral angle between the mean planes of the planar naphthyl and morpholine (chair) rings with the planar oxadiazol ring is 50.1(8) and 76.8(6)°, respectively. The planar naphthyl ring is twisted 52.2(5)° with the mean plane of the morpholine ring. A group of four intermolecular close contacts are observed between a bromine atom and hydrogen atoms from the closely packed naphthyl, morpholine and oxy–methyl groups in the unit cell. These molecular interactions in concert with an additional series of π–π stacking interactions that occur between the center of gravity of the two 6-membered rings of the naphthalene group influence the twist angles of each of these three groups. A MOPAC AM1 calculation of the conformation energy of the crystal structure [226.0128(9) kcal] compared to that of the minimum energy structure after geometry optimization [29.9744(1) kcal] reveals a significantly reduced value. The twist angles of the three groups above also change after the AM1 calculation giving support to the influence of both intermolecular C–H···Br short-range interactions and Cg π–π stacking interactions on these angles which therefore play a role in stabilizing crystal packing.Graphical AbstractCrystal structure of 5-{[(6-bromonaphthalen-2-yl)oxy]methyl}-3-(morpholin-4-ylmethyl)-1,3,4-oxadiazole-2(3H)-thione, C18H18BrN3O3S, is reported and its geometric and packing parameters described and compared to a MOPAC computational calculation.