Synthesis, crystal structure and Hirshfeld surface analysis of (3Z)-4-[(4-amino-1,2,5-oxadiazol-3-yl)-amino]-3-bromo-1,1,1-trifluorobut-3-en-2-one

被引:0
作者
Guseinov, Firudin I. [1 ,2 ]
Celikesir, Sevim Turktekin [3 ]
Akkurt, Mehmet [3 ]
Ovsyannikov, Viacheslav O. [2 ,4 ]
Ugrak, Bogdan I. [2 ]
Lavrova, Oksana M. [2 ]
Samigullina, Aida I. [2 ]
Bhattarai, Ajaya [5 ]
机构
[1] Kosygin State Univ Russia, Moscow 117997, Russia
[2] Russian Acad Sci, ND Zelinsky Inst Organ Chem, Moscow 119991, Russia
[3] Erciyes Univ, Dept Phys, Fac Sci, TR-38039 Kayseri, Turkiye
[4] Russian Technol Univ, Lomonosov Inst Fine Chem Technol, MIREA, Moscow 119571, Russia
[5] MMAMC Tribhuvan Univ, Dept Chem, Biratnagar, Nepal
来源
ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS | 2024年 / 80卷
关键词
crystal structure; alpha-haloketone; diaminofurazan; non-covalent interactions; oxadiazole ring; disorder; Hirshfeld surface analysis; COPPER(II) COMPLEXES; ARYLHYDRAZONE; IRON(III); CATALYSTS;
D O I
10.1107/S2056989024004080
中图分类号
O7 [晶体学];
学科分类号
0702 ; 070205 ; 0703 ; 080501 ;
摘要
In the title compound, C6H4BrF3N4O2, the oxadiazole ring is essentially planar with a maximum deviation of 0.003 (2) angstrom. In the crystal, molecular pairs are connected by N-H center dot center dot center dot N hydrogen bonds, forming dimers with an R-2(2)(8) motif. The dimers are linked into layers parallel to the (104) plane by N-H center dot center dot center dot O hydrogen bonds. In addition, C-O center dot center dot center dot pi and C-Br center dot center dot center dot pi interactions connect the molecules, forming a three-dimensional network. The F atoms of the trifluoromethyl group are disordered over two sites in a 0.515 (6): 0.485 (6) ratio. The intermolecular interactions in the crystal structure were investigated and quantified using Hirshfeld surface analysis.
引用
收藏
页码:582 / +
页数:8
相关论文
共 33 条
[1]   PATTERNS IN HYDROGEN BONDING - FUNCTIONALITY AND GRAPH SET ANALYSIS IN CRYSTALS [J].
BERNSTEIN, J ;
DAVIS, RE ;
SHIMONI, L ;
CHANG, NL .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1995, 34 (15) :1555-1573
[2]   Fluorine-a small magic bullet atom in the drug development: perspective to FDA approved and COVID-19 recommended drugs [J].
Chandra, Girish ;
Singh, Durg Vijay ;
Mahato, Gopal Kumar ;
Patel, Samridhi .
CHEMICAL PAPERS, 2023, 77 (08) :4085-4106
[3]   Iodine-containing furazan compounds: a promising approach to high-performance energetic biocidal agents [J].
Chang, Jinjie ;
Hu, Lu ;
Pang, Siping ;
He, Chunlin .
JOURNAL OF MATERIALS CHEMISTRY A, 2023, 11 (29) :15979-15985
[4]   Design, synthesis, and characterization of oxadiazolopyrazine analogs with application as anticancer agents [J].
Chen, Wei-Chia ;
Chen, Chia-Ling ;
Chang, Tzu-Ting ;
Hsieh, Feng-Chun ;
Chen, Wei-Sheng ;
Li, Wen-Shan .
JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 2022, 69 (02) :375-387
[5]   Structure-activity relationship studies of [1,2,5]oxadiazolo[3,4-b] pyrazine-containing polymyxin-selective resistance-modifying agents [J].
Dutta, Somnath ;
Liu, Nianzi ;
Gao, Yuefeng ;
Beck, Lily ;
Wang, Xiang .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2022, 72
[6]   WinGX and ORTEP for Windows: an update [J].
Farrugia, Louis J. .
JOURNAL OF APPLIED CRYSTALLOGRAPHY, 2012, 45 :849-854
[7]   The Cambridge Structural Database [J].
Groom, Colin R. ;
Bruno, Ian J. ;
Lightfoot, Matthew P. ;
Ward, Suzanna C. .
ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE CRYSTAL ENGINEERING AND MATERIALS, 2016, 72 :171-179
[8]   Chalcogen and Hydrogen Bonds at the Periphery of Arylhydrazone Metal Complexes [J].
Gurbanov, Atash, V ;
Kuznetsov, Maxim L. ;
Resnati, Giuseppe ;
Mahmudov, Kamran T. ;
Pombeiro, Armando J. L. .
CRYSTAL GROWTH & DESIGN, 2022, 22 (06) :3932-3940
[9]   Halogen bonding in cadmium(II) MOFs: its influence on the structure and on the nitroaldol reaction in aqueous medium [J].
Gurbanov, Atash, V ;
Kuznetsov, Maxim L. ;
Karmakar, Anirban ;
Aliyeva, Vusala A. ;
Mahmudov, Kamran T. ;
Pombeiro, Armando J. L. .
DALTON TRANSACTIONS, 2022, 51 (03) :1019-1031
[10]   Resonance Assisted Chalcogen Bonding as a New Synthon in the Design of Dyes [J].
Gurbanov, Atash, V ;
Kuznetsov, Maxim L. ;
Mahmudov, Kamran T. ;
Pombeiro, Armando J. L. ;
Resnati, Giuseppe .
CHEMISTRY-A EUROPEAN JOURNAL, 2020, 26 (65) :14833-14837