Succinic, fumaric, adipic and oxalic acid cocrystals of promethazine hydrochloride
Succinic, fumaric, adipic and oxalic acid cocrystals of promethazine hydrochloride
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DOI：
10.1107/s2053229618017904
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发表时间：
2019-02-01
影响因子：
0.8
通讯作者：
Bende, Attila
中科院分区：
文献类型：
--
作者：
Borodi, Gheorghe;Turza, Alexandru;Bende, Attila
盐酸异丙嗪[ PTZ-Cl;系统名称：N，N-二甲基-1-（10 H-吩噻嗪-10-基）丙烷-2-氯化铵]与琥珀酸（PTZ-Cl-琥珀酸，C17 H21 N2 S+中心点Cl-中心点0.5C（4）H（6）O（4）），富马酸（PTZ-Cl-富马酸，C17 H21 N2 S+中心点Cl-中心点0.5C（4）H（4）O（4））和己二酸（PTZ-Cl-己二酸，C17 H21 N2 S+中心点Cl-中心点0.5C（6）H（10）O（4））通过溶剂滴磨和从乙腈溶液中缓慢蒸发来制备，沿着在四氢呋喃（草酸半溶剂化物，PTZ-Cl-草酸，C17 H21 N2 S+中心点Cl-中心点0.5C（2）H2 O（4））和硝基甲烷（草酸氢盐，PTZ-草酸，C17 H21 N2 S+中心点C2 HO 4-）中制备的两种草酸共晶。通过从四氢呋喃和乙腈中结晶获得的晶体结构包括晶格结构中的Cl-离子，而通过从硝基甲烷（PTZ-草酸）中结晶获得的晶体结构中缺少Cl-离子。为了解释草酸形成的两种超分子构型，计算了两种溶剂存在下的分子间相互作用能，并利用密度泛函理论（DFT）确定了平衡构型.用X射线衍射、红外光谱和差示扫描量热法对共晶进行了研究。此外，还考察了特殊条件下的稳定性和水溶性。结晶的PTZ-Cl琥珀酸、PTZ-Cl富马酸和PTZ-Cl己二酸具有相似的晶格参数值，并显示2：1的PTZ-Cl与二羧酸的化学计量比。PTZ-Cl-草酸以2：1的化学计量比结晶，而缺少Cl原子的结构具有1：1的化学计量比。所有获得的晶体都显示PTZ中心点Cl中心点（二羧酸）中心点Cl中心点PTZ类型的氢键，除了PTZ-草酸盐，其在草酸氢盐和异丙嗪鎓离子之间形成分叉键，沿着在草酸氢盐阴离子之间形成无限氢键链。
Novel cocrystals of promethazine hydrochloride [ PTZ-Cl; systematic name: N, N-dimethyl-1-(10H-phenothiazin-10-yl) propan-2-aminium chloride] with succinic acid (PTZ-Cl-succinic, C17H21N2S+center dot Cl-center dot 0.5C(4)H(6)O(4)), fumaric acid (PTZ-Cl-fumaric, C17H21N2S+center dot Cl-center dot 0.5C(4)H(4)O(4)) and adipic acid (PTZ-Cl-adipic, C17H21N2S+center dot Cl-center dot 0.5C(6)H(10)O(4)) were prepared by solvent drop grinding and slow evaporation from acetonitrile solution, along with two oxalic acid cocrystals which were prepared in tetrahydrofuran (the oxalic acid hemisolvate, PTZ-Cl-oxalic, C17H21N2S+center dot Cl-center dot 0.5C(2)H(2)O(4)) and nitromethane (the hydrogen oxalate salt, PTZ-oxalic, C17H21N2S+center dot C2HO4-). The crystal structures obtained by crystallization from tetrahydrofuran and acetonitrile include the Cl- ion in the lattice structures, while the Cl- ion is missing from the crystal structure obtained by crystallization from nitromethane (PTZ-oxalic). In order to explain the formation of the two types of supramolecular configurations with oxalic acid, the intermolecular interaction energies were calculated in the presence of the two solvents and the equilibrium configurations were determined using density functional theory (DFT). The cocrystals were studied by X-ray diffraction, IR spectroscopy and differential scanning calorimetry. Additionally, a stability test under special conditions and water solubility were also investigated. PTZ-Clsuccinic, PTZ-Cl-fumaric and PTZ-Cl-adipic crystallized having similar lattice parameter values, and showed a 2:1 PTZ-Cl to dicarboxylic acid stoichiometry. PTZ-Cl-oxalic crystallized in a 2:1 stoichiometric ratio, while the structure lacking the Cl atom belongs has a 1:1 stoichiometry. All the obtained crystals exhibit hydrogen bonds of the type PTZ center dot center dot center dot Cl center dot center dot center dot(dicarboxylic acid)center dot center dot center dot Cl center dot center dot center dot PTZ, except for PTZ-oxalic, which forms bifurcated bonds between the hydrogen oxalate and promethazinium ions, along with an infinite hydrogen-bonded chain between the hydrogen oxalate anions.