Pseudo-polymorphism and crystal engineering: hydrogen-bonded supramolecular networks in trimethoprim m-chlorobenzoate and trimethoprim m-chlorobenzoate dihydrate
Pseudo-polymorphism and crystal engineering: hydrogen-bonded supramolecular networks in trimethoprim m-chlorobenzoate and trimethoprim m-chlorobenzoate dihydrate
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DOI：
10.1039/b211312k
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发表时间：
2003-01
期刊：
影响因子：
3.1
通讯作者：
S. B. Raj;P. Muthiah;U. Rychlewska;B. Warżajtis
中科院分区：
文献类型：
--
作者：
S. B. Raj;P. Muthiah;U. Rychlewska;B. Warżajtis
本文研究了甲氧苄氨苄间氯苯酸酯(1)和二水合甲氧苄氨苄间氯苯酸酯(2)两种拟多晶型的晶体结构。在这两种结构中，甲氧苄啶的嘧啶部分在其中一个环氮上被质子化。在这两种形式中，羧酸基与质子化嘧啶环相互作用形成环状氢键双分子基序。这些基序进一步自组织成两个不同的氢键网络。在化合物1中，两个中心对称相关基序通过氢键形成互补的四重氢键模式DDAA （D为氢键供体，a为氢键受体）阵列。在化合物2中，两个反转相关基序通过一对涉及2-氨基和N3原子的N - h⋯N氢键配对。除了配对之外，一个水分子在配对的两侧连接一个基序的4-氨基和另一个基序的羧酸氧，从而形成互补的线性氢键阵列。
This manuscript deals with the crystal structures of two pseudo-polymorphic forms, namely, trimethoprim m-chlorobenzoate (1) and trimethoprim m-chlorobenzoate dihydrate (2). In both the structures, the pyrimidine moieties of trimethoprim are protonated at one of the ring nitrogens. In both the forms, the carboxylate group interacts with the protonated pyrimidine ring to form the cyclic hydrogen-bonded bimolecular motif. These motifs are further self-organized into two different hydrogen-bonded networks. In compound 1, two of the centrosymmetrically-related motifs are hydrogen-bonded to give a complementary DDAA (D refers to the hydrogen bond donor and A refers to the hydrogen bond acceptor) array of quadruple hydrogen bonding pattern. In compound 2, two of the inversion-related motifs are paired through a pair of N–H⋯N hydrogen bonds involving the 2-amino group and the N3 atom. In addition to the pairing, one water molecule bridges the 4-amino group of one motif and the carboxylate oxygen of another motif on both sides of the pairing, leading to a complementary linear array of hydrogen bonds.