1,3-Dibenzyl­imidazolidine-2-thione

Anna Mietlarek-Kropidłowska; Jaroslaw Chojnacki; Barbara Becker

doi:10.1107/S1600536812032655

. 2012 Jul 21;68(Pt 8):o2521. doi: 10.1107/S1600536812032655

1,3-Dibenzylimidazolidine-2-thione

Anna Mietlarek-Kropidłowska ^a,^*, Jaroslaw Chojnacki ^a, Barbara Becker ^a

PMCID: PMC3414971 PMID: 22904958

Abstract

In the title compound, C₁₇H₁₈N₂S, the imidazolidine ring adopts a twisted conformation. In the crystal, molecules are linked by slipped π–π interactions between the benzene rings of neighbouring molecules [centroid-to-centroid distance = 3.903 (2) Å].

Related literature

For background information and the synthesis of related compounds, see: Savjani & Gajjar (2011 ▶); Wazeer et al. (2007 ▶); Zhivotova et al. (2006 ▶); Jayaram et al. (2008 ▶). For ring-puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C₁₇H₁₈N₂S
M _r = 282.39
Monoclinic,
a = 14.8492 (8) Å
b = 10.2284 (5) Å
c = 10.1314 (6) Å
β = 107.131 (6)°
V = 1470.53 (14) Å³
Z = 4
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 120 K
0.45 × 0.15 × 0.03 mm

Data collection

Oxford Xcalibur Sapphire2 diffractometer
Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T _min = 0.938, T _max = 0.993
5840 measured reflections
2890 independent reflections
2148 reflections with I > 2σ(I)
R _int = 0.020

Refinement

R[F ² > 2σ(F ²)] = 0.037
wR(F ²) = 0.092
S = 0.94
2890 reflections
181 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812032655/lx2257sup1.cif

e-68-o2521-sup1.cif^{(22.4KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812032655/lx2257Isup2.hkl

e-68-o2521-Isup2.hkl^{(139KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812032655/lx2257Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The research was supported by grants from the Polish Ministry of Education and Science (grant Nos. NN204 543339 and NN204 150237).

supplementary crystallographic information

Comment

2-Imidazolidinethione derivatives exhibit applications in diverse therapeutic areas such as antimicrobial activity (Wazeer et al., 2007). Moreover, 2-imidazolidinethiones are also used as a chiral auxiliary and ligands for asymmetric catalysis (Savjani & Gajjar, 2011). Herein, we report the crystal structure of the title compound.

In the title molecule (Fig. 1), the imidazolidine ring has twisted (T, i.e. half-chair) conformation. In the crystal structure (Fig. 2), molecules are connected by slipped π–π interactions between the benzene rings of neighbouring molecules, with a Cg–Cgⁱ distance of 3.903 (2) Å and an interplanar distance of 3.595 (2) Å resulting in a slippage of 1.519 Å (Cg is the centroid of the C5–C10 benzene ring).

The volume 1470.53 (14) Å³ as well as the number of molecules in the elemental cell (Z = 4) of 1,3-dibenzylimidazolidine-2-thione match the values determined for closely related 1,3-dibenzyl-1H-imidazole-2(3H)-thione (Jayaram et al., 2008). These molecules differ in their 5-membered ring being either aromatic or aliphatic. Nevertheless any closer comparison of the bond lengths and angles between these two compounds is difficult due to the lack of atomic coordinates for 1,3-dibenzyl-1H-imidazole-2(3H)-thione either in the above mentioned paper or in Cambridge Structural Database. The 5-membered imidazolidine ring in the present structure adopts the conformation which is most closely described as half-chair or twisted (T) on C2—C3. Parameter Q₂ (Cremer & Pople, 1975), which specifies the puckering amplitude and thus differentiate planar from non-planar systems, is significantly greater than zero 0.1565 (16) Å and φ₂ parameter is 301.2 (6)° pointing to the mentioned T type of pucker.

Experimental

The title compound was synthesized according to the procedure reported by Zhivotova et al. (2006). The reaction was carried out between N,N'-dibenzylethylenediamine and carbon disulfide in the presence of KOH (molar ratio 1:1:1) in methanol. The mixture was stirred 50 min, filtered and then left for crystallization at 278 K. After a week yellowish needle-like crystals were appeared. These were filtered off and dried. The melting point was determined to be 393 K.