Crystal structure of (Z)-2-hy­droxy-4-methyl-N′-(4-oxo-1,3-thia­zolidin-2-yl­idene)benzohydrazide trihydrate

Peijuan Li; Zizhen Kang; Xin Fan; Longfei Jin

doi:10.1107/S1600536814023356

. 2014 Oct 29;70(Pt 11):o1199. doi: 10.1107/S1600536814023356

Crystal structure of (Z)-2-hydroxy-4-methyl-N′-(4-oxo-1,3-thiazolidin-2-ylidene)benzohydrazide trihydrate

Peijuan Li ^a, Zizhen Kang ^a, Xin Fan ^a, Longfei Jin ^a,^*

PMCID: PMC4257310 PMID: 25484827

Abstract

In the title compound, C₁₁H₁₁N₃O₃S·3H₂O, the non-H atoms of the main molecule are approximately planar, with an r.m.s. deviation of 0.030 Å. There is a bifurcated intramolecular N—H⋯(O,S) hydrogen bond present forming S(6) and S(5) ring motifs. In the crystal, O—H⋯O and N—H⋯O hydrogen bonds link the molecules into a three-dimensional network.

Keywords: crystal structure; benzohydrazide; 1,3-thiazolidene; hydrogen bonding; biological activity

Related literature

For the biological activities of thiazolidin-4-one compounds, see: Jain et al. (2012 ▶); Verma & Saraf (2008 ▶); Singh et al. (1981 ▶). For the synthesis, see: Brown (1961 ▶). graphic file with name e-70-o1199-scheme1.jpg

Experimental

Crystal data

C₁₁H₁₁N₃O₃S·3H₂O
M _r = 319.33
Triclinic,
a = 7.3739 (12) Å
b = 8.5110 (13) Å
c = 12.493 (2) Å
α = 103.047 (2)°
β = 101.385 (2)°
γ = 92.532 (2)°
V = 745.5 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 296 K
0.21 × 0.20 × 0.18 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.950, T _max = 0.957
5460 measured reflections
2731 independent reflections
2266 reflections with I > 2σ(I)
R _int = 0.020

Refinement

R[F ² > 2σ(F ²)] = 0.052
wR(F ²) = 0.154
S = 1.10
2731 reflections
191 parameters
H-atom parameters constrained
Δρ_max = 0.53 e Å⁻³
Δρ_min = −0.44 e Å⁻³

Data collection: APEX2 (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814023356/lh5733sup1.cif

e-70-o1199-sup1.cif^{(256.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814023356/lh5733Isup2.hkl

e-70-o1199-Isup2.hkl^{(150.1KB, hkl)}

Click here for additional data file.^{(5.8KB, cml)}

Supporting information file. DOI: 10.1107/S1600536814023356/lh5733Isup3.cml

Click here for additional data file.^{(25.7KB, tif)}

. DOI: 10.1107/S1600536814023356/lh5733fig1.tif

The molecular structure of (I), showing 30% probability displacement ellipsoids. The solvent water molecules have been omitted for clarity. Dashed lines indicate hydrogen bonds.

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

. DOI: 10.1107/S1600536814023356/lh5733fig2.tif

Part of the crystal structure of (I) showing hydrogen bonds as dashed lines.

CCDC reference: 1030606

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

Table 1. Hydrogen-bond geometry (, ).

DHA	DH	HA	D A	DHA
O1H1OO5ⁱ	0.84	1.83	2.655(3)	167
N1H1AS1	0.86	2.51	2.941(2)	112
N1H1AO1	0.86	1.92	2.609(3)	137
N3H3BO4	0.86	1.89	2.739(4)	170
O4H4OAO3ⁱⁱ	0.84	2.10	2.813(4)	143
O4H4OBO6	0.81	1.81	2.587(4)	161
O5H5OAO2ⁱⁱⁱ	0.84	2.02	2.864(3)	178
O5H5OBO4	0.84	2.40	3.239(6)	180
O6H6OAO2^iv	0.84	2.11	2.947(4)	180
O6H6OBO2	0.84	2.02	2.862(3)	180

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

Acknowledgments

This work was supported by the Key Project of the Natural Science Foundation of Hubei Province, China (grant No. 2008CDA067) and the Students Science and Technology Innovation Funds of the South-Central University for Nationalities.

supplementary crystallographic information

S1. Comment

4-Thiazolidinones are compounds which have a sulfur atom at position 1, a nitrogen atom at position 3 and a carbonyl group at position 4. Derivatives of 4-thiazolidinone exhibit prominent biological activites such as antibacterial, antifungal, antitubercular, anticancer, antiinflammtory, analgesic, anticonvulsant, antidepressant, antiviral/anti-HIV, antidiabetic, muscarinic receptor 1 agonist, FSH receptor agonist, trypanocidal (anti-epimastigote) and antiarrhythmic activity (Jain, et al., 2012; Verma & Saraf, 2008; Singh et al., 1981). Several hydrogen bond acceptor sites exist in these compounds, which could potentially lead to the formation of supermolecular structures. As part of our ongoing studies, the preparation and X-ray structure determination of the title compound, (I), was undertaken.

In the title molecule (Fig. 1) the bond lengths show normal ranges of values. The non-hydrogen atoms of the main molecule are approximately planar with an r.m.s. deviation of 0.030Å. There is a bifurcated intramolecular N—H···(O,S) hydrogen bond present forming S(6) and S(5) ring motifs. In the crystal, O—H···O and N—H···O hydrogen bonds form a three-dimensional network (Fig. 2).

S2. Experimental

The synthesis followed the prodecures of Brown (1961). 4-(4-Methyl salicyloyl) thiosemicarbazide (2.25 g, 0.01 mol), ethyl bromoacetate (3.34 g, 0.02 mol) and 50 ml of ethyl alcohol were added to a round-bottom flask. The mixture was stirred for 10 minutes, then slowly warmed to boiling and stirred for 8 h. After cooling to room temperature, 40 ml of water were added and the reaction mixture was left for 12 h. The resulting precipitate was filtered and recrystallized with ethyl alcohol to give 2.30 g of the title compound. Single crystals suitable for X-ray diffraction analysis were growned by slow evaporation of a solution of the title compound in methanol/water/ether (20:7:5) at room temperature.