Crystal structure of 3-benzyl-1-[(1,2,3,4-tetra­hydro­naphthalen-1-yl­idene)amino]­thio­urea

Shaaban K Mohamed; Joel T Mague; Mehmet Akkurt; Alaa A Hassan; Ahmed T Abdel-Aziz; Mustafa R Albayati

doi:10.1107/S2056989015021064

. 2015 Nov 21;71(Pt 12):o974–o975. doi: 10.1107/S2056989015021064

Crystal structure of 3-benzyl-1-[(1,2,3,4-tetrahydronaphthalen-1-ylidene)amino]thiourea

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

PMCID: PMC4719930 PMID: 26870558

Abstract

In the title compound, C₁₈H₁₉N₃S, the dihedral angle between the planes of the benzene rings is 58.63 (8)°. The six-membered ring bonded to the thiosemicarbazide group (r.m.s. deviation = 0.038 Å) adopts a sofa conformation, with one of the methylene-group C atoms as the flap. A short intramolecular N—H⋯N contact is observed. In the crystal, molecules are linked by weak N—H⋯S interactions to generate C(4) chains propagating in the [010] direction, with adjacent molecules related by glide symmetry.

Keywords: crystal structure, thiosemicarabazides, antiproliferative agents

Related literature

For the antitumour activities of thiosemicarbazides, see: Vandresen et al. (2014 ▸); Xie et al. (2014 ▸); Gan et al. (2014 ▸). For the synthesis of the title compound, see: Mague et al. (2014 ▸)

Experimental

Crystal data

C₁₈H₁₉N₃S
M _r = 309.42
Orthorhombic,
a = 11.9129 (5) Å
b = 9.6914 (4) Å
c = 27.8220 (11) Å
V = 3212.1 (2) Å³
Z = 8
Cu Kα radiation
μ = 1.77 mm⁻¹
T = 150 K
0.22 × 0.18 × 0.05 mm

Data collection

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2014 ▸) T _min = 0.84, T _max = 0.91
61936 measured reflections
3155 independent reflections
2795 reflections with I > 2σ(I)
R _int = 0.050

Refinement

R[F ² > 2σ(F ²)] = 0.035
wR(F ²) = 0.098
S = 1.06
3155 reflections
199 parameters
H-atom parameters constrained
Δρ_max = 0.56 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Data collection: APEX2 (Bruker, 2014 ▸); cell refinement: SAINT (Bruker, 2014 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXT (Bruker, 2014 ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ▸); molecular graphics: DIAMOND (Brandenburg & Putz, 2012 ▸); software used to prepare material for publication: SHELXTL (Bruker, 2014 ▸).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015021064/hb7536sup1.cif

e-71-0o974-sup1.cif^{(1.9MB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015021064/hb7536Isup2.hkl

e-71-0o974-Isup2.hkl^{(252.4KB, hkl)}

Click here for additional data file.^{(6.2KB, cml)}

Supporting information file. DOI: 10.1107/S2056989015021064/hb7536Isup3.cml

Click here for additional data file.^{(1.2MB, tif)}

. DOI: 10.1107/S2056989015021064/hb7536fig1.tif

The title molecule with 50% probability displacement ellipsoids.

Click here for additional data file.^{(1.4MB, tif)}

b . DOI: 10.1107/S2056989015021064/hb7536fig2.tif

Packing viewed down the b axis. N—H⋯S interactions are shown by dotted lines.

CCDC reference: 1435397

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
N1—H1A⋯N3	0.91	2.20	2.6219 (16)	108
N1—H1A⋯S1ⁱ	0.91	2.85	3.5790 (13)	138

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Symmetry code: (i) Inline graphic .

Acknowledgments

The support of NSF–MRI Grant No. 1228232 for the purchase of the diffractometer and Tulane University for support of the Tulane Crystallography Laboratory are gratefully acknowledged.

supplementary crystallographic information

S1. Comment

Recently, several kinds of thiosemicarbazone derivatives were synthesized and their antitumor activities were also reported (Vandresen et al., 2014; Xie et al., 2014; Gan et al., 2014). As part of our studies in this area, we report here the synthesis and crystal structural determination of the title compound.

In the title molecule (Fig. 1), the dihedral angle between the phenyl ring (C1–C6) and the aromatic portion of the tetrahydronaphthylidene unit (C13–C18) is 58.64 (5)°. A Cremer-Pople analysis of the conformation of the C9–C13,C18 ring gave puckering parameters Q = 0.434 (2) Å, θ = 126.2 (2)° and φ = 305.1 (2)°. The molecules pack in chains running parallel to the b axis assisted by weak N1—H1A···S1ⁱ (i: 1/2 - x, -1/2 + y, z) interactions (Table 1, Fig. 2).

S2. Experimental

The title compound was prepared according to our recently reported method (Mague et al., 2014). The product was recrystallized from ethanol solution to afford colorless tablets (90% yield) M.p. 413 - 414 K.