Crystal structure of methyl (2Z)-2-[(2Z)-2-(2-cyclo­pentyl­idenehydrazin-1-yl­idene)-4-oxo-3-phenyl-1,3-thia­zolidin-5-yl­idene]ethano­ate

Mehmet Akkurt; Victoria A Smolenski; Shaaban K Mohamed; Jerry P Jasinski; Alaa A Hassan; Mustafa R Albayati

doi:10.1107/S2056989015017454

. 2015 Sep 26;71(Pt 10):o776–o777. doi: 10.1107/S2056989015017454

Crystal structure of methyl (2Z)-2-[(2Z)-2-(2-cyclopentylidenehydrazin-1-ylidene)-4-oxo-3-phenyl-1,3-thiazolidin-5-ylidene]ethanoate

Mehmet Akkurt ^a, Victoria A Smolenski ^b, Shaaban K Mohamed ^c,^d, Jerry P Jasinski ^b, Alaa A Hassan ^d, Mustafa R Albayati ^e,^*

PMCID: PMC4647441 PMID: 26594474

Abstract

In the title compound, C₁₇H₁₇N₃O₃S, the cyclopentane ring is disordered over two sets of sites with an occupancy ratio of 0.775 (8):0.225 (8) for the affected atoms. The thiazolidinyl ring is planar (r.m.s. deviation = 0.024 Å) and forms a dihedral angle of 65.13 (8)° with the attached phenyl ring. The molecular packing is stabilized by C—H⋯O and C—H⋯π interactions, forming a three-dimensional structure.

Keywords: crystal structure, thiazolidinyl ring, disorder, hydrogen bonding, C—H⋯π interactions

Related literature

For biological properties of thiazole-containing compounds, see: Quiroga et al. (2002 ▸); Hutchinson et al. (2002 ▸); Hargrave et al. (1983 ▸); Patt et al. (1992 ▸); Sharma et al. (2009 ▸); Jaen et al. (1990 ▸); Tsuji & Ishikawa (1994 ▸); Bell et al. (1995 ▸): Ergenc et al. (1999 ▸); Carter et al. (1999 ▸); Badorc et al. (1997 ▸); Rudolph et al. (2001 ▸).

Experimental

Crystal data

C₁₇H₁₇N₃O₃S
M _r = 343.40
Monoclinic,
a = 5.5215 (3) Å
b = 16.1299 (8) Å
c = 18.7112 (9) Å
β = 93.980 (5)°
V = 1662.42 (15) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 296 K
0.28 × 0.08 × 0.04 mm

Data collection

Agilent Xcalibur, Eos, Gemini diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014 ▸) T _min = 0.850, T _max = 1.000
11300 measured reflections
5503 independent reflections
3958 reflections with I > 2σ(I)
R _int = 0.036

Refinement

R[F ² > 2σ(F ²)] = 0.050
wR(F ²) = 0.135
S = 1.02
5503 reflections
222 parameters
H-atom parameters constrained
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2014 ▸); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS2014 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ▸; 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/S2056989015017454/tk5388sup1.cif

e-71-0o776-sup1.cif^{(27.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015017454/tk5388Isup2.hkl

e-71-0o776-Isup2.hkl^{(301.7KB, hkl)}

Click here for additional data file.^{(6.7KB, cml)}

Supporting information file. DOI: 10.1107/S2056989015017454/tk5388Isup3.cml

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

. DOI: 10.1107/S2056989015017454/tk5388fig1.tif

View of the title compound showing only the major component of the disorder. Displacement ellipsoids for non-H atoms are drawn at the 50% probability level.

Click here for additional data file.^{(2.9MB, tif)}

a . DOI: 10.1107/S2056989015017454/tk5388fig2.tif

The molecular packing viewed down a axis. The C—H⋯O interactions are shown as dotted lines with non-participating H atoms omitted for clarity.

CCDC reference: 1425685

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

Table 1. Hydrogen-bond geometry (, ).

Cg4 is the centroid of the C9C14 ring.

DHA	DH	HA	D A	DHA
C13H13O2ⁱ	0.93	2.35	3.245(2)	163
C15H15O3ⁱⁱ	0.93	2.56	3.485(2)	172
C17H17AO1ⁱⁱ	0.96	2.42	3.269(2)	147
C3AH3A2Cg4ⁱⁱⁱ	0.97	2.96	3.914(3)	169

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

Acknowledgments

JPJ acknowledges the NSF–MRI program (grant No. CHE-1039027) for funds to purchase the X-ray diffractometer.

supplementary crystallographic information

S1. Comment

Thiazoles are important class of heterocyclic compounds, found in many potent biologically active molecules such as sulfathiazol (antimicrobial drug), Ritonavir (antiretroviral drug), Abafungin (antifungal drug), with trade name Abasol cream, and Bleomycine and Tiazofurin (antineoplastic drug). It has been noted over the years that interesting biological activities (Quiroga et al., 2002; Hutchinson et al., 2002) were associated with thiazole derivatives. Applications of thiazoles were found in drug development for the treatment of allergies (Hargrave et al., 1983), hypertension (Patt et al., 1992), inflammation (Sharma et al., 2009), schizophrenia (Jaen et al., 1990), bacteria infection (Tsuji & Ishikawa, 1994), HIV infection (Bell et al., 1995), hypnotics (Ergenc et al., 1999) and for the treatment of pain (Carter et al., 1999), as fibrinogen receptor antagonists with antithrombotic activity (Badorc et al., 1997) and as new inhibitors of bacterial DNA gyrase B (Rudolph et al., 2001). In this context we report in this study the synthesis and crystal structure of the title compound.

The molecular structure of the title compound is shown in Fig. 1. The major and minor components of the disordered cyclopentane ring [0.775 (8):0.225 (8)] adopt an envelope conformations with atoms C2A and C2B as the flap in each component. The puckering parameters are Q(2) 0.274 (3) Å, φ (2) = 42.7 (6)° for major component, and Q(2) 0.253 (8) Å, φ (2) = 209.6 (16)° for minor component. The central 1,3-thiazolidine ring (S1/N3C6–C8) makes a dihedral angle of 65.13 (8)° with the phenyl ring (C9–C14).

In the crystal, C—H···O and C—H···π interactions stabilize the molecular packing, forming a three-dimensional network, Fig. 2 and Table 1.

S2. Experimental

A mixture of 2-cyclopentylidene-N-phenylhydrazinecarbothioamide (1 mmol, 233 mg) and dimethyl but-2-ynedioate (1 mmol, 142 mg) in ethylacetate (10 ml) was stirred and refluxed at 350 K. The reaction progress was monitored by TLC until completion. On cooling, a solid yellow product was precipitated, filtered off, dried under vacuum and recrystallized from ethanol to afford yellow crystals.