Crystal structure of 1-(adamantan-1-yl)-3-(4-bromophenyl)thiourea, C₁₇H₂₁BrN₂S

Abstract

C17H 21 BrN 2 S, orthorhombic, Pbca (No. 61), a = 17.0675(7) Å, CCDC no.: 1449483The asymmetric unit of the crystal structure is shown in the gure. Tables 1 and 2 contain details of the measurement method and a list of the atoms including atomic coordinates and displacement parameters. Source of materialTo a solution of 1-adamantylamine (1.51 g, 0.01 mol) in ethanol (15 mL), 4-bromophenyl isothiocyanate (2.14 g, 0.01 mol) was added and the mixture was heated under re ux for three hours. On cooling, the precipitated crude product was ltered, dried and crystallized from ethanol to yield 3.36 g (92%) of the title compound (C17H 21 BrN 2 S) as transparent block crystals. M.P.:

Probing the Effect of Halogen Substituents (Br, Cl, and F) on the Non-covalent Interactions in 1-(Adamantan-1-yl)-3-arylthiourea Derivatives: A Theoretical Study

“…The investigated 1-(adamantan-1-yl)-3-arylthiourea derivatives 1 – 4 were synthesized in almost quantitative yields by condensation of adamantan-1-yl isothiocyanate A with the appropriate primary aromatic amine B via stirring in dichloromethane at room temperature (Scheme ). The synthesis of compounds 1 , 2 , 3 , and 4 was previously reported via the reaction of adamantan-1-ylamine with the corresponding aryl isothiocyanate in ethanol in 76, 88, 85, and 92% yields, respectively. − …”

“…On the other hand, thiourea derivatives were proved to possess diverse chemotherapeutic properties including anticancer, − antiviral, − antituberculosis, and antimalarial activities . In addition to diverse biological activities, thiourea derivatives are utilized as precursors for biologically active derivatives. − In view of the above, we prepared 1-(adamantan-1-yl)-3-arylthiourea derivatives, and brief structural reports were described earlier. − The reported structures revealed that the thiourea moiety adopted two different conformations such as anti–anti and anti–syn conformations. The bromo and chloro derivatives adopted the anti–anti conformation, whereas the unsubstituted derivative and the p -fluoro derivative exhibited the anti–syn conformation.…”

“…The previous structural studies of the title 1-(adamantan-1-yl)-3-arylthiourea derivatives did not provide details on the halogen substituent effect and conformational importance of anti–anti and anti–syn conformations of the thiourea unit present in them. To obtain a better understanding of the molecular conformation, the role of non-covalent interactions to the crystal packing, and the effect of different halogen substituents, we have performed different theoretical analyses using the reported 3D structures of 1-(adamantan-1-yl)-3-arylthiourea derivatives. − Moreover, a complete understating of weak non-covalent forces is vital to generate a new application in different disciplines. The molecular properties of crystalline solids primarily depend on the molecular arrangement, and various non-covalent forces control this arrangement.…”