Crystal structure of 1-(adamantan-1-yl)-3-(3-chlorophenyl)thiourea, C17H21ClN2S

Al-Omary, Fatmah A. M.; Al-Rasheed, Lamees S.; Ghabbour, Hazem A.; El-Emam, Ali A.

doi:10.1515/ncrs-2016-0117

Cited by 5 publications

(5 citation statements)

References 25 publications

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“…The anti–anti conformation is observed in the parent and the fluoro derivatives, while the anti–syn conformation is preferred by the bromo and chloro derivatives. The same anti–syn conformation was also observed in a related structure in which chlorine is attached at the meta position of the phenyl ring (CSD refcode: RAPNOO ) …”

Section: Results and Discussionsupporting

confidence: 67%

“…The same anti− syn conformation was also observed in a related structure in which chlorine is attached at the meta position of the phenyl ring (CSD refcode: RAPNOO). 29 In order to obtain the conformational landscape of title molecules, we carried out a relaxed potential energy surface (PES) scan around C−N bonds (dihedral angles T1 and T2) of the thiourea unit. Figure 3 shows the energy change as a function of the C−N bond rotation.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…Similar features are also noted when the chlorine substituent is attached at the meta position of the phenyl ring (3-Cl, csd refcode: RAPNOO). 29 We can see from Figure 5 the large and intense red areas shown for the N−H•••S interaction, suggesting its vital role in the stabilization.…”

Section: The Dissociation Energies For C−h•••s and N−h•••c(π) Interac...mentioning

confidence: 85%

“…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.…”

Section: Introductionmentioning

confidence: 99%

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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

et al. 2021

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The effect of halogen substituents (X = Br, Cl, and F) on the crystal packing and intra-and intermolecular interactions in four adamantane−thiourea hybrid derivatives is investigated using different theoretical tools. The bromo and chloro derivatives exhibit 3D isostructurality as evident from lattice parameters, molecular conformation, and crystal packing. The density functional theory study suggests that the molecular conformation of the parent (unsubstituted) and fluoro derivatives exhibits a stable low energy anti−syn conformation. In contrast, bromo and chloro derivatives adopt stable and relatively high energy minima on their potential energy surfaces. Hirshfeld surface analysis reveals the effect of halogen substituents on the intermolecular contacts. The halogen atoms mainly reduce the contribution of H•••H contacts toward crystal packing. PIXEL energy analysis indicates the strong dimer formed by N−H•••S hydrogen bonds in all four structures. It also revealed that a vast number of H•••H contacts observed in different dimers of these structures either presented along with other conventional interactions or solely stabilize the dimeric topology. The topological parameters for intermolecular interactions in these structures suggest an intermediate bonding character between shared and closed-shell interactions for N−H•••S hydrogen bonds in the parent and chloro derivatives. In contrast, the N−H•••S hydrogen bond in other structures is of a closed-shell interaction. Among four derivatives, the fluoro derivative is weakly packed in the solid state based on the PIXEL method's lattice energy calculation.

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Section: Results and Discussionsupporting

confidence: 67%

Section: ■ Results and Discussionmentioning

confidence: 99%

Section: The Dissociation Energies For C−h•••s and N−h•••c(π) Interac...mentioning

confidence: 85%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

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

et al. 2021

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“…The adamantyl isothiourea derivatives 1 and 2 were synthesized via condensation of 1-adamantylamine A with phenyl isothiocyanate or 3-chlorophenyl isothiocyanate to yield the corresponding 1-(adamantan-1-yl)-3-arylthiourea derivatives B (Al-Wahaibi et al, 2016) and C (Al-Omary et al, 2017), which were reacted with 4-bromobenzyl bromide in the presence of potassium carbonate to yield the target compounds 1 and 2 (Scheme 1).…”

Section: Synthesis and Crystallizationmentioning

confidence: 99%

X-ray and theoretical investigation of (Z)-3-(adamantan-1-yl)-1-(phenyl or 3-chlorophenyl)-S-(4-bromobenzyl)isothioureas: an exploration involving weak non-covalent interactions, chemotherapeutic activities and QM/MM binding energy

Al-Omary

Gude

Al-Rasheed

et al. 2020

Journal of Biomolecular Structure and Dynamics

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A detailed exploration of crystal packing of two adamantane-isothiourea hybrid derivatives along with a known closely related structure has been performed to delineate the effect of halogen substituents and the role of weak intermolecular interactions in their supramolecular architectures. The adamantane-isothiourea hybrid derivatives used in the present study are (Z)-3-(Adamantan-1-yl)-S-(4-bromobenzyl)-1-phenylisothiourea (1), C 24 H 27 BrN 2 S and (Z)-3-(Adamantan-1-yl)-S-(4-bromobenzyl)-1-(3chlorophenyl)isothiourea (2), C 24 H 26 BrClN 2 S, characterized by X-ray crystallography. The X-ray structures revealed that the molecular conformation of 1 and 2 are different and stabilized by intramolecular C-HÁÁÁN interactions. In addition, a short intramolecular HÁÁÁH contact is formed in 2. The Hirshfeld surface analysis was used to delineate the nature of different intermolecular interactions and their contributions toward crystal packing. The quantitative analysis of strengths of molecular dimers existed in 1 and 2 has been performed using the PIXEL method. The electrostatic potential map clearly revealed nature and strength of r-holes at Br and Cl atoms. The topological analysis was used to characterize the nature and the strength of various intermolecular interactions including the type I BrÁÁÁBr contact. Interestingly, all the H-H bonding observed in 1 and 2 show closed-shell in nature. Further, an in-vitro antimicrobial activity studies suggest that the title compounds exhibited potent antibacterial activity against all the tested Gram-positive bacterial strains and Gram-negative Escherichia coli. Compound 2 showed marked anti-proliferative activity against MCF-7 and HeLa cell lines.

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Synthesis, physical properties, and computational biological activity of N-{[(3(4)-halophenyl)amino]carbonothioyl}adamantane-1-carboxamides

Kuznetsov,

Ilyina,

Butov

et al. 2023

Russ Chem Bull

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Crystal structure of 1-(adamantan-1-yl)-3-(3-chlorophenyl)thiourea, C₁₇H₂₁ClN₂S

Abstract: CCDC no.: 1482683The asymmetric unit of the title 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.

Cited by 5 publications

References 25 publications

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

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

X-ray and theoretical investigation of (Z)-3-(adamantan-1-yl)-1-(phenyl or 3-chlorophenyl)-S-(4-bromobenzyl)isothioureas: an exploration involving weak non-covalent interactions, chemotherapeutic activities and QM/MM binding energy

Synthesis, physical properties, and computational biological activity of N-{[(3(4)-halophenyl)amino]carbonothioyl}adamantane-1-carboxamides

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