Citation: Shu-Wang GE, Bai-Wang SUN. Synthesis, Crystal Structure, Spectroscopy and Hirshfeld Analysis of 4, 6-Diamino-2-cyclopropylaminopyrimidine-5-carbonitrile with Different Solvents: N, N-dimethylformamide, Methanol and Water[J]. Chinese Journal of Structural Chemistry, ;2022, 41(3): 220327. doi: 10.14102/j.cnki.0254-5861.2011-3359 shu

Synthesis, Crystal Structure, Spectroscopy and Hirshfeld Analysis of 4, 6-Diamino-2-cyclopropylaminopyrimidine-5-carbonitrile with Different Solvents: N, N-dimethylformamide, Methanol and Water

Shu-Wang GE ,
Bai-Wang SUN ^,

School of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, China

Author Bio: Ge Shu-Wang. E-mail: geshuwang1@126.com
Corresponding author: Bai-Wang SUN, chmsunbw@seu.edu.cn
Received Date: 9 September 2021
Accepted Date: 18 November 2021

Fund Project: the National Natural Science Foundation of China 21371031the National Natural Science Foundation of China 21628101

Figures(11)

Three new solvates of 4, 6-diamino-2-cyclopropylamino-5-pyrimidine carbonitrile (DCL): crystal 1 (DCL with N, N-dimethylformamide (DMF)), crystal 2 (DCL with methanol) and crystal 3 (DCL with water) were synthesized and characterized by single-crystal X-ray diffraction, thermal behaviour, Hirshfeld surface and powder X-ray powder diffraction (PXRD). ¹H and ¹³C NMR spectra confirm solvent molecules existing in the crystal lattice. Crystal 1 forms a 1:1 DCL: DMF crystal; crystal 2 gives a 1:0.5 DCL: methanol crystal and crystal 3 gets a 1:1.5 DCL: H₂O crystal. The three crystals are all primarily stabilized by a strong N–H⋅⋅⋅N hydrogen bonding interaction between DCL and the solvents. The structures are stabilized by H⋅⋅⋅H, N–H⋅⋅⋅O, N–H⋅⋅⋅N and O–H⋅⋅⋅O intermolecular interactions. When crystal 2 is dried at 150 ℃, the new polymorph with no solvate is obtained.
- dicyclanil,
- crystal,
- spectroscopy,
- Hirshfeld surfaces
1. [1]
  Krivoshein, A. V. Molecular pharmaceutics and solid-state chemistry of drugs. Curr. Pharm. Des. 2016, 22, 4881–4882. doi: 10.2174/1381612822666160826115401
2. [2]
  Morissette, S. L.; Soukasene, S.; Levinson, D.; Cima, M. J.; Almarsson, O. Elucidation of crystal form diversity of the HIV protease inhibitor ritonavir by high-throughput crystallization. PNAS 2003, 100, 2180–2184. doi: 10.1073/pnas.0437744100
3. [3]
  Trotta, J. T.; Zeidan, T. A.; Tilak, P. A.; Foxman, B. M.; Almarsson, O.; Oliveira, M. A.; Chiarella, R. A.; Hickey, M. B.; Remenar, J. F. Aripiprazole and dehydro-aripiprazole solid solutions: crystalline combinations of drug and active metabolite in tailored compositions. Cryst. Growth Des. 2020, 20, 3944–3956. doi: 10.1021/acs.cgd.0c00263
4. [4]
  Springuel, G.; Leyssens, T. Innovative chiral resolution using enantiospecific co-crystallization in solution. Cryst. Growth Des. 2012, 12, 3374–3378.
5. [5]
  Alieva, A.; Boyes, M.; Vetter, T.; Casiraghi, C. Selective polymorphism of alpha-glycine by acoustic levitation. CrystEngComm. 2020, 22, 7075–7081. doi: 10.1039/D0CE00856G
6. [6]
  Luo, Y. H.; Sun, B. W. Co-crystallization of pyridine-2-carboxamide with a series of alkyl dicarboxylic acids with different carbon chain: crystal structure, spectroscopy and Hirshfeld analysis. Spectrochimi. Acta A 2014, 120, 228–236. doi: 10.1016/j.saa.2013.09.144
7. [7]
  Safari, F.; Olejniczak, A.; Katrusiak, A. Pressure-promoted solvation of resorcinol. Cryst. Growth Des. 2020, 20, 3112–3118. doi: 10.1021/acs.cgd.9b01732
8. [8]
  Bucar, D. K.; Lancaster, R. W.; Bernstein, J. Disappearing polymorphs revisited. Angew. Chem. Int. Ed. 2015, 54, 6972–6993.
9. [9]
  Wawrzycka-Gorczyca, I.; Borowski, P.; Osypiuk-Tomasik, J.; Mazur, L.; Koziol, A. E. Crystal structure of olanzapine and solvates. Part 3. Two and three-component solvates with water, ethanol, butan-2-ol and dichloromethane. J. Mol. Struct. 2007, 830, 188–197. doi: 10.1016/j.molstruc.2006.07.017
10. [10]
  Food safety commission of Japan. Dicyclanil. Food Safety 2018, 6, 136–138.
11. [11]
  Matthew, W.; Richard, W. Evaluation of dicyclanil (CLiKZiN^®) treatment for the early-season protection of ewes against blowfly strike. Vet Parasitol. 2012, 188, 200–202. doi: 10.1016/j.vetpar.2012.03.016
12. [12]
  Luo, Y. H.; Wang, J. W.; Li, Y. J.; Chen, C.; An, P. J.; Wang, S. L.; You, C. Q.; Sun, B. W. Selective separation of aqueous sulphate anions via crystallization of sulphate-water clusters. CrystEngComm. 2017, 19, 3362–3369.
13. [13]
  Marti, E.; Oechslein, W.; Geoffroy, A. J. Dicyclanil polmorphs and hydrates and their prepration. Patent WO99/10333. 1998-08-25.
14. [14]
  Lau, K. K. Vetrinary compsiton. Patent. AU2010100438. 2010-05-07.
15. [15]
  Rigaku. Anonymous. X-ray Spectrom. 2002, 30, 195–195.
16. [16]
  Sheldrick, G. M. SHELXS97: Programs for Crystal Structure Analysis. University of Göttingen. Germany 1997.
17. [17]
  Wang, J. W.; Zhang, Y. W.; Wang, M. X.; Luo, Y. H.; Sun, B. W. Assembly of 6-aminonicotinic acid and inorganic anions into different dimensionalities: crystal structure, absorption properties and Hirshfeld surface analysis. Polyhedron 2017, 124, 243–250.
18. [18]
  Mercury 2.3 Supplied with Cambridge Structural Database, CCDC: Cambridge, U. K.
19. [19]
  Brandenburg, K. DIAMOND: Crystal and Molecular Structure Visualization. Version 3.1b. Crystal Impact GbR. Bonn. Germany 2006.
20. [20]
  Wolff, S. K.; Grimwood, D. J.; McKinnon, J. J.; Jayatilaka, D.; Spackman, M. A. Crystal Explorer 1.5, University of Western Australia, Perth, Australia.
21. [21]
  Luo, Y. H.; Sun, B. W. Pharmaceutical Co-crystals of pyrazinecarboxamide (PZA) with various carboxylic acids: crystallography, Hhirshfeld surfaces, and dissolution study. Cryst. Growth Des. 2013, 13, 2098–2106.
22. [22]
  Fabbiani, F. P. A.; Byrne, L. T.; McKinnon, J. J.; Spackman, M. A. Solvent inclusion in the structural voids of form II carbamazepine: single-crystal X-ray diffraction, NMR spectroscopy and Hirshfeld surface analysis. CrystEngComm. 2007, 9, 728–731.
23. [23]
  Parkin, A.; Barr, G.; Dong, W.; Gilmore, C. J.; Jayatilaka, D.; McKinnon, J. J.; Spackman, M. A.; Wilson, C. C. Comparing entire crystal structures: structural genetic fingerprinting. CrystEngComm. 2007, 9, 648–652.
24. [24]
  Luo, Y. H.; Zhang, C. G.; Xu, B.; Sun, B. W. A cocrystal strategy for the precipitation of liquid 2, 3-dimethyl pyrazine with hydroxyl substituted benzoic acid and a Hirshfeld surfaces analysis of them. CrystEngComm. 2012, 14, 6860–6868.
25. [25]
  Luo, Y. H.; Wang, Y.; Zhao, J.; Wang, Y. H. A thermally labile copper(II) complex with hetero N- and O-donor ligands: crystal structure, Hirshfeld surfaces, thermal and luminescent properties. Spectrochimi. Acta A 2014, 122, 246–252.
1. [1]
  Ling-Hao Zhao , Hai-Wei Yan , Jian-Shuang Jiang , Xu Zhang , Xiang Yuan , Ya-Nan Yang , Pei-Cheng Zhang . Effective assignment of positional isomers in dimeric shikonin and its analogs by ¹H NMR spectroscopy. Chinese Chemical Letters, 2024, 35(5): 108863-. doi: 10.1016/j.cclet.2023.108863
2. [2]
  Chengde Wang , Liping Huang , Shanshan Wang , Lihao Wu , Yi Wang , Jun Dong . A distinction of gliomas at cellular and tissue level by surface-enhanced Raman scattering spectroscopy. Chinese Chemical Letters, 2024, 35(5): 109383-. doi: 10.1016/j.cclet.2023.109383
3. [3]
  Jiakun Bai , Junhui Jia , Aisen Li . An elastic organic crystal with piezochromic luminescent behavior. Chinese Journal of Structural Chemistry, 2024, 43(6): 100323-100323. doi: 10.1016/j.cjsc.2024.100323
4. [4]
  Peng Meng , Qian-Cheng Luo , Aidan Brock , Xiaodong Wang , Mahboobeh Shahbazi , Aaron Micallef , John McMurtrie , Dongchen Qi , Yan-Zhen Zheng , Jingsan Xu . Molar ratio induced crystal transformation from coordination complex to coordination polymers. Chinese Chemical Letters, 2024, 35(4): 108542-. doi: 10.1016/j.cclet.2023.108542
5. [5]
  Jun Lu , Jinrui Yan , Yaohao Guo , Junjie Qiu , Shuangliang Zhao , Bo Bao . Controlling solid form and crystal habit of triphenylmethanol by antisolvent crystallization in a microfluidic device. Chinese Chemical Letters, 2024, 35(4): 108876-. doi: 10.1016/j.cclet.2023.108876
6. [6]
  Ce Liang , Qiuhui Sun , Adel Al-Salihy , Mengxin Chen , Ping Xu . Recent advances in crystal phase induced surface-enhanced Raman scattering. Chinese Chemical Letters, 2024, 35(9): 109306-. doi: 10.1016/j.cclet.2023.109306
7. [7]
  Xiumei LI , Yanju HUANG , Bo LIU , Yaru PAN . Syntheses, crystal structures, and quantum chemistry calculation of two Ni(Ⅱ) coordination polymers. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 2031-2039. doi: 10.11862/CJIC.20240109
8. [8]
  Fengyu Zhang , Yali Liang , Zhangran Ye , Lei Deng , Yunna Guo , Ping Qiu , Peng Jia , Qiaobao Zhang , Liqiang Zhang . Enhanced electrochemical performance of nanoscale single crystal NMC811 modification by coating LiNbO₃. Chinese Chemical Letters, 2024, 35(5): 108655-. doi: 10.1016/j.cclet.2023.108655
9. [9]
  Na Wang , Wang Luo , Huaiyi Shen , Huakai Li , Zejiang Xu , Zhiyuan Yue , Chao Shi , Hengyun Ye , Leping Miao . Crystal engineering regulation achieving inverse temperature symmetry breaking ferroelasticity in a cationic displacement type hybrid perovskite system. Chinese Chemical Letters, 2024, 35(5): 108696-. doi: 10.1016/j.cclet.2023.108696
10. [10]
  Zhijia Zhang , Shihao Sun , Yuefang Chen , Yanhao Wei , Mengmeng Zhang , Chunsheng Li , Yan Sun , Shaofei Zhang , Yong Jiang . Epitaxial growth of Cu_2-xSe on Cu (220) crystal plane as high property anode for sodium storage. Chinese Chemical Letters, 2024, 35(7): 108922-. doi: 10.1016/j.cclet.2023.108922
11. [11]
  Min Chen , Boyu Peng , Xuyun Guo , Ye Zhu , Hanying Li . Polyethylene interfacial dielectric layer for organic semiconductor single crystal based field-effect transistors. Chinese Chemical Letters, 2024, 35(4): 109051-. doi: 10.1016/j.cclet.2023.109051
12. [12]
  Zhi-Yuan Yue , Hua-Kai Li , Na Wang , Shan-Shan Liu , Le-Ping Miao , Heng-Yun Ye , Chao Shi . Dehydration-triggered structural phase transition-associated ferroelectricity in a hybrid perovskite-type crystal. Chinese Chemical Letters, 2024, 35(10): 109355-. doi: 10.1016/j.cclet.2023.109355
13. [13]
  Chao LIU , Jiang WU , Zhaolei JIN . Synthesis, crystal structures, and antibacterial activities of two zinc(Ⅱ) complexes bearing 5-phenyl-1H-pyrazole group. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1986-1994. doi: 10.11862/CJIC.20240153
14. [14]
  Zhenghua ZHAO , Qin ZHANG , Yufeng LIU , Zifa SHI , Jinzhong GU . Syntheses, crystal structures, catalytic and anti-wear properties of nickel(Ⅱ) and zinc(Ⅱ) coordination polymers based on 5-(2-carboxyphenyl)nicotinic acid. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 621-628. doi: 10.11862/CJIC.20230342
15. [15]
  Lu LIU , Huijie WANG , Haitong WANG , Ying LI . Crystal structure of a two-dimensional Cd(Ⅱ) complex and its fluorescence recognition of p-nitrophenol, tetracycline, 2, 6-dichloro-4-nitroaniline. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1180-1188. doi: 10.11862/CJIC.20230489
16. [16]
  Weizhong LING , Xiangyun CHEN , Wenjing LIU , Yingkai HUANG , Yu LI . Syntheses, crystal structures, and catalytic properties of three zinc(Ⅱ), cobalt(Ⅱ) and nickel(Ⅱ) coordination polymers constructed from 5-(4-carboxyphenoxy)nicotinic acid. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1803-1810. doi: 10.11862/CJIC.20240068
17. [17]
  Kaimin WANG , Xiong GU , Na DENG , Hongmei YU , Yanqin YE , Yulu MA . Synthesis, structure, fluorescence properties, and Hirshfeld surface analysis of three Zn(Ⅱ)/Cu(Ⅱ) complexes based on 5-(dimethylamino) isophthalic acid. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1397-1408. doi: 10.11862/CJIC.20240009
18. [18]
  Xinting XIONG , Zhiqiang XIONG , Panlei XIAO , Xuliang NIE , Xiuying SONG , Xiuguang YI . Synthesis, crystal structures, Hirshfeld surface analysis, and antifungal activity of two complexes Na(Ⅰ)/Cd(Ⅱ) assembled by 5-bromo-2-hydroxybenzoic acid ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1661-1670. doi: 10.11862/CJIC.20240145
19. [19]
  Liyang ZHANG , Dongdong YANG , Ning LI , Yuanyu YANG , Qi MA . Crystal structures, luminescent properties and Hirshfeld surface analyses of three cadmium(Ⅱ) complexes based on 2-(3-(pyridin-2-yl)-1H-pyrazol-1-yl)benzoate. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1943-1952. doi: 10.11862/CJIC.20240079

Get Citation

PDF

XML

Metrics

PDF Downloads(5)
Abstract views(471)
HTML views(74)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142