间硝基苯甲酸/8-羟基喹啉(1/1)共晶体结构解析与Rietveld精修
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摘要
通过溶液冷却结晶法制备出间硝基苯甲酸/8-羟基喹啉(1/1)共晶体。利用粉末X线衍射技术及傅里叶红外光谱技术采集该共晶体的粉末衍射数据及红外光谱数据。对该共晶体粉末衍射数据进行指标化及晶体结构解析,并参照红外分析结果对该共晶体的晶体结构进行了Rietveld精修,最终测定了间硝基苯甲酸/8-羟基喹啉(1/1)共晶体的晶体结构。该共晶体的一个不对称单元中包含一个间硝基苯甲酸分子(去质子化的)和一个8-羟基喹啉分子(质子化的)。8-羟基喹啉上的酚羟基和芳香N原子与间硝基苯甲酸上的羧基通过O—H…O氢键、N—H…O氢键形成二聚体,沿b轴方向相互平行的二聚体之间存在着π…π堆砌作用。
An organic cocrystal of m-nitrobenzoic acid/8-hydroxyquinoline( 1/1) was obtained through crystallization. Powder X-ray diffraction data and infrared spectroscopy data were collected and the indexing and crystallographic structural analyses of the cocrystal were carried out followed by Rietveld refinement. Proton transfer from m-nitrobenzoic acid to 8-hydroxyquinoline was revealed via fourier transform infrared spectroscopy. The asymmetric unit of the crystal structure had one deprotonated mnitrobenzoic acid and one protonized 8-hydroxyquinoline.The phenol group and the aromatic N atom in 8-hydroxyquinoline were involved in hydrogen bonding with carboxylic group in m-nitrobenzoic acid,resulting in a dimmer of m-nitrobenzoic acid/8-hydroxyquinoline.The π…π stacking interactions between the dimmers along the b-axis were observed. The hydrogen bonding and π…π stacking interactions were analyzed and their role in crystal packing was investigated.
An organic cocrystal of m-nitrobenzoic acid/8-hydroxyquinoline( 1/1) was obtained through crystallization. Powder X-ray diffraction data and infrared spectroscopy data were collected and the indexing and crystallographic structural analyses of the cocrystal were carried out followed by Rietveld refinement. Proton transfer from m-nitrobenzoic acid to 8-hydroxyquinoline was revealed via fourier transform infrared spectroscopy. The asymmetric unit of the crystal structure had one deprotonated mnitrobenzoic acid and one protonized 8-hydroxyquinoline.The phenol group and the aromatic N atom in 8-hydroxyquinoline were involved in hydrogen bonding with carboxylic group in m-nitrobenzoic acid,resulting in a dimmer of m-nitrobenzoic acid/8-hydroxyquinoline.The π…π stacking interactions between the dimmers along the b-axis were observed. The hydrogen bonding and π…π stacking interactions were analyzed and their role in crystal packing was investigated.
引文
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[6]HIENDRAWAN S,VERIANSYAH B,WIDJOJOKUSUMO E,et al.Physicochemical and mechanical properties of paracetamol cocrystal with 5-nitroisophthalic acid[J].International journal of pharmaceutics,2016,497(1/2):106.
[7]DING X H,LI Y H,WANG S,et al.Proton-transfer supramolecular salts of D-/L-tartaric acid and 1-(2-pyrimidyl)piperazine[J].Journal of molecular structure,2014,1062:61.
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[9]JIN S W,LU X H,WANG D Q,et al.Crystal and molecular structure of four 1∶1 adducts from 2-methylquinoline and different acidic components[J].Journal of molecular structure,2012,1010:17.
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[11]TREMAYNE M.The impact of powder diffraction on the structural characterization of organic crystalline materials[J].Philosophical transactions of the royal society A:mathematical physical&engineering sciences,2004,362:2691.
[12]董水超,陶亚秋,沈晓冬,等.粉末X线衍射测定间氨基苯甲酸/富马酸(2/1)有机盐晶体结构[J].南京工业大学学报(自然科学版),2014,36(2):83.
[13]ACCELRYS.Materials studio[CP].San Diego:Accelrys Inc,2011.
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[15]BALLABH A.Hydrogen bonded supramolecular network in organic salts:crystal structures of acid:base salts of dicarboxylic acids and amines[J].Crystengcomm,2002,4:135.