Crystal structure of (E)-2-[(4-chloro-2H-chromen-3-yl)methyl­idene]-N-cyclo­hexyl­hydrazinecarbo­thio­amide

Rajeswari Gangadharan; Jebiti Haribabu; Ramasamy Karvembu; K Sethusankar

doi:10.1107/S1600536814018509

. 2014 Aug 23;70(Pt 9):o1039–o1040. doi: 10.1107/S1600536814018509

Crystal structure of (E)-2-[(4-chloro-2H-chromen-3-yl)methylidene]-N-cyclohexylhydrazinecarbothioamide

Rajeswari Gangadharan ^a, Jebiti Haribabu ^b, Ramasamy Karvembu ^b, K Sethusankar ^c,^*

PMCID: PMC4186115 PMID: 25309214

Abstract

In the title compound, C₁₇H₂₀ClN₃OS, the mean plane of the central thiourea core makes dihedral angles of 26.56 (9) and 47.62 (12)° with the mean planes of the chromene moiety and the cyclohexyl ring, respectively. The cyclohexyl ring adopts a chair conformation. The N–H atoms of the thiourea unit adopt an anti conformation. The chromene group is positioned trans, whereas the cyclohexyl ring lies in the cis position to the thione S atom, with respect to the thiourea C—N bond. In the crystal, molecules are linked by N—H⋯S hydrogen bonds, forming inversion dimers enclosing R ² ₂(8) ring motifs. The dimers are linked by C—H⋯Cl hydrogen bonds, enclosing R ⁶ ₆(44) ring motifs, forming sheets lying parallel to (010).

Keywords: crystal structure, chromene, hydrazine, thioamide, cyclohexyl, hydrogen bonds

Related literature

For the biological properties of thiosemicarbazones, see: Prabhakaran et al. (2007 ▶); Kelly et al. (1996 ▶); West et al. (1993 ▶); Pérez et al. (1999 ▶). For their optical properties and applications, see: Tian et al. (1997 ▶); Uesugi et al. (1994 ▶). For a related structure, see: Jayakumar et al. (2011 ▶). graphic file with name e-70-o1039-scheme1.jpg

Experimental

Crystal data

C₁₇H₂₀ClN₃OS
M _r = 349.87
Orthorhombic,
a = 12.2857 (12) Å
b = 15.3082 (16) Å
c = 18.5241 (18) Å
V = 3483.9 (6) Å³
Z = 8
Mo Kα radiation
μ = 0.35 mm⁻¹
T = 296 K
0.30 × 0.25 × 0.20 mm

Data collection

Bruker SMART APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T _min = 0.901, T _max = 0.933
18568 measured reflections
4291 independent reflections
2762 reflections with I > 2σ(I)
R _int = 0.033

Refinement

R[F ² > 2σ(F ²)] = 0.050
wR(F ²) = 0.152
S = 1.02
4291 reflections
208 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814018509/su2769sup1.cif

e-70-o1039-sup1.cif^{(20.1KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814018509/su2769Isup2.hkl

e-70-o1039-Isup2.hkl^{(210.4KB, hkl)}

Click here for additional data file.^{(6.5KB, cml)}

Supporting information file. DOI: 10.1107/S1600536814018509/su2769Isup3.cml

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

. DOI: 10.1107/S1600536814018509/su2769fig1.tif

The molecular structure of the title molecule, with atom labelling. The displacement ellipsoids are drawn at the 30% probability level.

Click here for additional data file.^{(1.3MB, tif)}

a . DOI: 10.1107/S1600536814018509/su2769fig2.tif

The crystal packing of the title compound viewed along the a axis. The hydrogen bonds are shown as dashed lines (see Table 1 for details; H atoms not involved in hydrogen bonding have been omitted for clarity).

CCDC reference: 1016441

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
N2—H2A⋯S1ⁱ	0.86	2.73	3.507 (2)	151
C12—H12⋯Cl1ⁱⁱ	0.98	2.83	3.689 (2)	147

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

Acknowledgments

The authors thank Professors D. Velmurugan and T. Srinivasan of the Centre for Advanced Study in Crystallography and Biophysics, University of Madras, Chennai, India, for the data collection.

supplementary crystallographic information

S1. Experimental

An ethanol solution of N-cyclohexylhydrazinecarbothioamide (1.736 g, 0.01 mole) was added to a ethanol solution (50 cm³) of 4-chloro-2H-chromene-3-carbaldehyde (1.94 g, 0.01 mole). The mixture was refluxed for 2 h during which time a yellow precipitate separated out. The reaction mixture was then cooled to room temperature and the precipitate was filtered off. It was then washed with ethanol and dried under vacuum (Yield: 85%). Crystals of the title compound were obtained by slow evaporation of a solution in ethanol.