Crystal structure of N-(propan-2-yl­carbamo­thio­yl)benzamide

Jerry P Jasinski; Mehmet Akkurt; Shaaban K Mohamed; Mohamed A Gad; Mustafa R Albayati

doi:10.1107/S2056989014027133

. 2015 Jan 1;71(Pt 1):o56–o57. doi: 10.1107/S2056989014027133

Crystal structure of N-(propan-2-ylcarbamothioyl)benzamide

Jerry P Jasinski ^a, Mehmet Akkurt ^b, Shaaban K Mohamed ^c,^d, Mohamed A Gad ^e, Mustafa R Albayati ^f,^*

PMCID: PMC4331893 PMID: 25705507

Abstract

In the crystal structure of the title compound, C₁₁H₁₄N₂OS, the six atoms of the central C₂N₂OS residue are coplanar (r.m.s. deviation = 0.002 Å), which facilitates the formation of an intramolecular N—H⋯O hydrogen bond, which closes an S(6) loop. The terminal phenyl ring is inclined with respect to the central plane [dihedral angle = 42.10 (6)°]. The most prominent feature of the crystal packing is the formation of {⋯HNCS}₂ synthons resulting in centrosymmetric dimers.

Keywords: crystal structure, thiourea, conformation, hydrogen bonding

Related literature

For use of thioureas as building blocks in the synthesis of various organic compounds, see: Burgeson et al. (2012 ▸); Vega-Pérez et al. (2012 ▸); Yao et al. (2012 ▸); Shantharam et al. (2013 ▸); Yang et al. (2013 ▸). For use of thiourea-containing compounds in medicinal applications, see: Rodriguez-Fernandez et al. (2005 ▸); Rauf et al. (2012 ▸). graphic file with name e-71-00o56-scheme1.jpg

Experimental

Crystal data

C₁₁H₁₄N₂OS
M _r = 222.30
Monoclinic,
a = 11.2147 (4) Å
b = 5.3988 (2) Å
c = 19.6834 (7) Å
β = 102.031 (4)°
V = 1165.57 (7) Å³
Z = 4
Cu Kα radiation
μ = 2.27 mm⁻¹
T = 293 K
0.28 × 0.22 × 0.18 mm

Data collection

Agilent Xcalibur, Eos, Gemini diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014 ▸) T _min = 0.828, T _max = 1.000
3844 measured reflections
2189 independent reflections
1944 reflections with I > 2σ(I)
R _int = 0.025

Refinement

R[F ² > 2σ(F ²)] = 0.049
wR(F ²) = 0.146
S = 1.08
2189 reflections
146 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2014 ▸); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS2014 (Gruene et al., 2014 ▸); program(s) used to refine structure: SHELXL2014 (Gruene et al., 2014 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸); software used to prepare material for publication: PLATON (Spek, 2009 ▸).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989014027133/tk5351sup1.cif

e-71-00o56-sup1.cif^{(20.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989014027133/tk5351Isup2.hkl

e-71-00o56-Isup2.hkl^{(120.4KB, hkl)}

Click here for additional data file.^{(4.2KB, cml)}

Supporting information file. DOI: 10.1107/S2056989014027133/tk5351Isup3.cml

Click here for additional data file.^{(1.1MB, tif)}

. DOI: 10.1107/S2056989014027133/tk5351fig1.tif

Perspective view of the title molecule with atom labeling scheme and 50% probability ellipsoids.

Click here for additional data file.^{(2.5MB, tif)}

b . DOI: 10.1107/S2056989014027133/tk5351fig2.tif

Packing viewed down the b axis showing stacks of pairs of molecules connected by N—H⋯S interactions.

CCDC reference: 1038725

Additional supporting information: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (, ).

DHA	DH	HA	D A	DHA
N1H1NS1ⁱ	0.81(2)	2.66(2)	3.4439(19)	165(2)
N2H2NO1	0.87(2)	2.00(3)	2.662(2)	132(2)

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Symmetry code: (i) Inline graphic .

Acknowledgments

JPJ acknowledges the NSF–MRI program (grant No. CHE-1039027) for funds to purchase the X-ray diffractometer. SKM would like to thank Keene State College for providing the X-ray data and Manchester Metropolitan University for supporting this study.

supplementary crystallographic information

S1. Structural commentary

Compounds containing thiourea linkage are very useful building blocks for the synthesis of a wide range of multiheterocyclic and macromolecular compounds. Thioureas have proved to be useful substances in drug research in recent years (Burgeson et al., 2012; Vega-Pérez et al., 2012; Yao et al., 2012; Shantharam et al., 2013; Yang et al., 2013). Symmetrical and unsymmetrical thioureas have shown anti-fungal activity against the plant pathogens like Penicillium expansum and Fusarium oxysporum (Rodriguez-Fernandez et al., 2005). Also, 1,3-dialkyl or diaryl thioureas exhibited significant anti-fungal activity against Pyricularia oryzae and Drechslera oryzae (Rauf et al., 2012). In light of this, and following to our on-going study in synthesis of bio-active molecules, we report here the synthesis and crystal structure of the title compound.

In the structure of the title compound, Fig. 1, intramolecular N—H···O and intermolecular N—H···S interactions are noted (Table 1).

S2. Synthesis and crystallization

Freshly prepared benzoyl chloride 5 ml (0.043 mol) was added drop wise to a solution of 3.2 g (0.042 mol) of ammonium thiocyanate in 20 ml dry acetone with stirring. The reaction mixture was refluxed for 3 h. The obtained solid precipitate ammonium chloride was filtered off. The formed benzoyl isothiocyanate in the filtrate was added to a solution of 3.1 ml (0.0425 mol) of 2-amino-isopropane in 20 ml dry acetone. The reaction mixture was heated under reflux for 5 h, then poured into a beaker containing some ice cubes. The resulting precipitate was collected by filtration, washed several times with cold ethanol/water and purified by recrystallization from ethanol/dichloromethane mixture (1:1). Yield (63%); colourless solid, m.p 418 K.

S3. Refinement

Carbon-bound H-atoms were placed in calculated positions (C—H = 0.93 to 0.98 Å) and were included in the refinement in the riding model approximation, with U_iso(H) = 1.2–1.5U_eq(C). The hydrogen atoms attached to N1 and N2 were found from difference Fourier maps and were refined with the distance contratin N—H = 0.86±0.02 Å with unrestrained U_iso.