Diphenyl­methyl isothio­cyanate

Pei-Hua Zhao; Jun-Jie Liu; Mei Zhang; Gui-Zhe Zhao; Ya-Qing Liu

doi:10.1107/S1600536812000888

. 2012 Jan 14;68(Pt 2):o388. doi: 10.1107/S1600536812000888

Diphenylmethyl isothiocyanate

Pei-Hua Zhao ^a,^*, Jun-Jie Liu ^a, Mei Zhang ^a, Gui-Zhe Zhao ^a, Ya-Qing Liu ^a

PMCID: PMC3275065 PMID: 22347010

Abstract

The asymmetric unit of the title compound, C₁₄H₁₁NS, contains two molecules in which the dihedral angles between the phenyl rings are 77.23 (7) and 86.30 (7)°. No aromatic π–π stacking interactions are observed.

Related literature

For the synthetic applications of isothiocyanates, see: Fernandez et al. (1995 ▶); Mukerjee & Ashare (1991 ▶); Stephensen & Zaragosa (1997 ▶).

Experimental

Crystal data

C₁₄H₁₁NS
M _r = 225.30
Triclinic,
a = 9.635 (5) Å
b = 10.222 (6) Å
c = 11.974 (7) Å
α = 98.491 (13)°
β = 95.296 (15)°
γ = 93.573 (6)°
V = 1157.9 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 113 K
0.24 × 0.20 × 0.18 mm

Data collection

Rigaku Saturn724 CCD diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T _min = 0.943, T _max = 0.957
12035 measured reflections
5430 independent reflections
3169 reflections with I > 2σ(I)
R _int = 0.042

Refinement

R[F ² > 2σ(F ²)] = 0.034
wR(F ²) = 0.079
S = 0.89
5430 reflections
289 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812000888/hb6596sup1.cif

e-68-0o388-sup1.cif^{(22.1KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812000888/hb6596Isup2.hkl

e-68-0o388-Isup2.hkl^{(265.8KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812000888/hb6596Isup3.cml

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

Acknowledgments

This work was supported financially by the Start-up Foundation and the Youth Foundation of North University of China.

supplementary crystallographic information

Experimental

Diphenylamine (44.0 mmol) was dissolved in absolute ethanol (50.0 ml). Carbon disulfide (440.0 mmol) and triethylamine (44.0 mmol) were added while stirring. The reaction mixture was stirred for 0.5 h at room temperature and then cooled on an ice bath. Di-tert butyl dicarbonate (43.6 mmol) dissolved in absolute ethanol (10.0 ml), was added followed by the immediate addition of a catalytic amount of 1,4-diazabicyclo-[2.2.2]octane (0.88 mmol) in absolute ethanol (10.0 ml). The reaction mixture was kept in the ice bath for 5 min, and was then allowed to room temperature. After the reaction was completed, the solvents were evporated thoroughly in vacuo. The residue obtained was taken up in ether and filtered off, and the filtrate was evaporated in vacuo to afford the crude. The crude was separated through column chromatography on silica gel eluting with petroleum ether- dichloromethane (30:1 v/v) to give the white product. Colourless prisms of the title compound were obtained by slow evaporation of the dichloromethane/n-hexane solutions at room temperature. ¹H-NMR(400 MHz, CDCl₃, TMS): 6.02 (s, 1H, CH), 7.33–7.42 (m, 10H, Ph—H) p.p.m.. ¹³C-NMR(100 MHz,CDCl₃, TMS): 64.6 (CH), 126.7, 128.4, 129.0, 139.3 (Ph—CH and Ph—C) p.p.m..