Crystal structure of (Z)-3-(adamantan-1-yl)-1-(3-chlorophenyl)-S-benzylisothiourea, C₂₄H₂₇ClN₂S

Abstract

C 24 H 27 ClN 2 S, triclinic P1 (no. 2), a = 7.1670(3) Å, b = 12.2734(6) Å, c = 13.1560(6) Å, α = 109.605(2)°, β = 96.515(2)°, γ = 97.312(2)°, V = 1066.08(8) Å 3 , Z = 2, The asymmetric unit of the title crystal structure is shown in the figure. Tables 1 and 2 contain details on crystal structure and measurement conditions and a list of the atoms including atomic coordinates and displacement parameters. Source of materialBenzyl bromide (342 mg, 2.0 mmol) and anhydrous potassium carbonate (277 mg, 2.0 mmol) were added to a solution 1-(adamantan-1-yl)-3-(3-chlorophenyl)thiourea (642 mg, 2.0 mmol), in acetone (10 mL), and the mixture was heated under reflux for 3 h. The solvent was distilled off in vacuo, and the residue was washed with water, dried and recrystallized from ethanol to yield 625 mg (76%) of the title compound as transparent block crystals. M.P.: 367-369 K. Single crystals were obtained by slow evaporation of a EtOH/CHCl 3 (1:1) solution at room temperature.

Novel Adamantane-Linked Isothiourea Derivatives as Potential Chemotherapeutic Agents: Synthesis, Structural Insights, and Antimicrobial/Anti-Proliferative Profiles

“…Details are included in Figures S1–S4. Data support a double-bond character for N2–C11, whereas a simple bond character is evidenced for the N1–C11 bond, in agreement with similar structures previously reported. , Together with the residual density found near the N1 atom, it confirms that N1 is protonated in both structures.…”

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

“…Another two torsion angles s 4 and s 5 which define the rotation of methylene phenyl moiety are different in molecule 2 compared to other molecules (Figure 1(c)). Four fused six-membered rings constitute the adamantane moiety and the Cremer and Pople puckering parameters (Cremer & Pople, 1975) indicates that each of these six-membered ring exhibits chair conformation as observed in related adamantane structures (Al-Wahaibi et al 2018;El-Emam et al, 2017;. In 1-3, the molecular conformation is found to be stabilized with two intramolecular C-HÁÁÁN (involving two protons of adamantane and N2 of thiourea moiety) except in molecule 2 wherein only one intramolecular C-HÁÁÁN interaction.…”

“…The molecular structures of 1 and 2 that differ with respect to the chlorine substituent on C16 (ring A). In closely-related reported structure namely (Z)-3-(adamantan-1-yl)-1-(3-chlorophenyl)-S-benzylisothiourea (3), the bromine substituent is absent (El-Emam et al, 2017). The compound 1 crystallizes in the triclinic P-1 space group with two crystallographically independent molecules in the asymmetric unit.…”

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

“…Further, the adamantane moiety contains four fused six-membered rings, and these rings adopt a chair conformation as observed in related adamantane structures. − The chair conformation is confirmed by the Cremer and Pople puckering parameters …”