1-[(Cyclo­hexyl­idene)amino]-3-(prop-2-en-1-yl)thio­urea

Shaaban K Mohamed; Joel T Mague; Mehmet Akkurt; Alaa A Hassan; Mustafa R Albayati

doi:10.1107/S1600536814014834

. 2014 Jun 25;70(Pt 7):o827–o828. doi: 10.1107/S1600536814014834

1-[(Cyclohexylidene)amino]-3-(prop-2-en-1-yl)thiourea

Shaaban K Mohamed ^a,^b, Joel T Mague ^c, Mehmet Akkurt ^d, Alaa A Hassan ^b, Mustafa R Albayati ^e,^*

PMCID: PMC4120545 PMID: 25161602

Abstract

The asymmetric unit of the title compound, C₁₀H₁₇N₃S, consists of three symmetry-independent molecules with distinctly different conformations, as indicated for example by the C—N—C—C torsion angles of −155.9 (3), 89.9 (3) and 81.1 (4)° along the bond between thiourea and allyl units. In the crystal, molecules are connected via N—H⋯N and N—H⋯S hydrogen bonds into chains extending along [110] that are further associated through C—H⋯N interactions into layers parallel to (001). The allyl group in one of the independent molecules is disordered over two sets of sites with an occupancy ratio of 0.853 (6):0.147 (6).

Keywords: crystal structure

Related literature

For the use of thiosemicarbazides as intermediates in the synthesis of different heterocyclic compounds, see: Mague et al. (2014 ▶); Mohamed et al. (2014 ▶); Akkurt et al. (2014a ▶). For the bioactivity of thiosemicarbazones, see: Bahat et al. (2006 ▶); Qandil et al. (2006 ▶); Singh et al. (2001 ▶; Kalyoncuoğlu et al. (1992 ▶) Bahadur & Goel (1976 ▶). For the synthesis of the title compound, see: Akkurt et al. (2014b ▶). graphic file with name e-70-0o827-scheme1.jpg

Experimental

Crystal data

C₁₀H₁₇N₃S
M _r = 211.32
Triclinic,
a = 8.4772 (15) Å
b = 11.180 (2) Å
c = 19.766 (4) Å
α = 77.864 (3)°
β = 82.777 (3)°
γ = 74.879 (3)°
V = 1763.0 (5) Å³
Z = 6
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 150 K
0.26 × 0.15 × 0.10 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2013 ▶) T _min = 0.65, T _max = 0.98
31443 measured reflections
8701 independent reflections
5402 reflections with I > 2σ(I)
R _int = 0.080

Refinement

R[F ² > 2σ(F ²)] = 0.072
wR(F ²) = 0.217
S = 1.04
8701 reflections
383 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.70 e Å⁻³
Δρ_min = −0.60 e Å⁻³

Data collection: APEX2 (Bruker, 2013 ▶); cell refinement: SAINT (Bruker, 2013 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXT (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2012 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536814014834/gk2613sup1.cif

e-70-0o827-sup1.cif^{(930.1KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814014834/gk2613Isup2.hkl

e-70-0o827-Isup2.hkl^{(476.5KB, hkl)}

Click here for additional data file.^{(4.5KB, cml)}

Supporting information file. DOI: 10.1107/S1600536814014834/gk2613Isup3.cml

CCDC reference: 1009841

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N8—H8⋯S1ⁱ	0.91	2.47	3.356 (2)	164
N1—H1A⋯N6	0.91	2.40	3.185 (3)	145
N2—H2A⋯S3ⁱⁱ	0.91	2.42	3.290 (2)	161
C10—H10B⋯N9ⁱⁱⁱ	0.99	2.67	3.590 (4)	155
N4—H4A⋯N3	0.91	2.15	2.979 (3)	152
N5—H5A⋯N9	0.91	2.24	3.153 (3)	176
C16—H16B⋯N9	0.99	2.42	3.410 (4)	177
N7—H7⋯S2	0.91	2.51	3.363 (2)	155
C26—H26A⋯N2^iv	0.99	2.67	3.626 (4)	163
C26—H26A⋯N3^iv	0.99	2.60	3.499 (4)	152

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) .

Acknowledgments

JTM thanks Tulane University for support of the Tulane Crystallography Laboratory.

supplementary crystallographic information

S1. Comment

It is well known that thiosemicarbazides are the key intermediates used in the synthesis of many heterocyclic compounds such as thiazolidinones (Mague et al., 2014), triazols (Mohamed et al., 2014) and thiazoles (Akkurt et al., 2014a). Thiosemicarbazone derivatives have displayed various pharmacological properties such as analgesic (Bahat et al., 2006), anti-bacterial (Qandil et al., 2006), anti-fungal, anti-tumoral (Singh et al., 2001; Kalyoncuoğlu et al., 1992) and anti-tubercular (Bahadur & Goel, 1976) activities. In view of these findings and as part of ongoing research in the domain of heterocyclic compounds of the 1,2,4-triazole class with expected biological activity we report the synthesis and crystal structure of the title compound.

The asymmetric unit consists of three independent molecules having distinctly different conformations as indicated by the torsion angles C4–N1–C3–C2 (-155.9 (3)°), C14–N4–C13–C12 (89.9 (3)°) and C24–N7–C23–C22 (81.1 (4)°) for the allyl group. These molecules are associated via N—H···N hydrogen bonds (Fig. 1 and Table 1).

The packing consists of layers parallel to (001) formed by molecules joined via N—H···N hydrogen bonds, N—H···S and C—H···N interactions (Fig. 2 and Table 1).

S2. Experimental

The title compound was prepared according to our previously reported method (Akkurt et al., 2014b). Colourless crystals suitable for X-ray diffraction were obtained by crystallization from ethanol (m.p. 438 K).