organic compounds
(Z)-3-(2-Hydroxyethyl)-2-(phenylimino)-1,3-thiazolidin-4-one
aChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, bChemistry Department, Faculty of Science, Sohag University, Sohag 82524, Egypt, and cDepartment of Chemistry, University of Otago, PO Box 56, Dunedin, New Zealand
*Correspondence e-mail: jsimpson@alkali.otago.ac.nz
In the title compound, C11H12N2O2S, the thiazole and phenyl rings are inclined at 56.99 (6)° to one another. The thiazole ring is planar with an r.m.s. deviation for the five ring atoms of 0.0274 Å. The presence of the phenylimine substituent is confirmed with the C=N distance to the thiazole ring of 1.2638 (19) Å. The molecule adopts a Z conformation with respect to this bond. The –OH group of the hydroxyethyl substituent is disordered over two positions with relative occupancies 0.517 (4) and 0.483 (4). In the crystal, O—H⋯O hydrogen bonds, augmented by C—H⋯N contacts, form dimers with R22(11) rings and generate chains along the b axis. Parallel chains are linked in an obverse fashion by weak C—H⋯S hydrogen bonds. C—H⋯O hydrogen bonds together with C—H⋯π contacts further consolidate the structure, stacking molecules along the b axis.
Related literature
For pharmaceutical background to thiazolidinone compounds, see: Shah & Desai (2007); Subudhi et al. (2007); Kuecuekguezel et al. (2006); Mehta et al. (2006); Srivastava et al. (2006); Zhou et al. (2008). For our recent work on the synthesis of bio-selective molecules, see: Mohamed et al. (2012). For related structures, see: Bally & Mornon (1973); Moghaddam & Hojabri (2007); Yella et al. (2008); Abdel-Aziz et al. (2012). For standard bond distances, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995).
Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2011); cell APEX2 and SAINT (Bruker, 2011); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008) and TITAN (Hunter & Simpson, 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) and TITAN; molecular graphics: SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97, enCIFer (Allen et al., 2004), PLATON (Spek, 2009) and publCIF (Westrip, 2010).
Supporting information
https://doi.org/10.1107/S1600536812030243/tk5126sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812030243/tk5126Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536812030243/tk5126Isup3.cml
To a well stirred mixture of 135 mg (1 mmol) phenylisothiocyanate and 61 mg (1 mmol) 2-aminoethanol in 50 ml dioxane, 167 mg (1 mmol) of bromo ethylacetate was added. The reaction mixture was refluxed and monitored by TLC until completion after 3 h. A solid product was deposited on cooling to room temperature and collected by filtration. The crude product was recrystallized from ethanol to give a high quality crystals (M.p. 327 K) suitable for X-ray analysis in an excellent yield (92%).
The OH group of the hydroxyethyl substituent is disordered over two positions O2 and O3 with relative occupancies that converged to 0.517 (4) and 0.483 (4). Displacement parameters for the C13 atom bound to the disordered OH groups were slightly higher than normal but a suitable additional disorder model could not be found. All H-atoms bound to carbon were refined using a riding model with d(C—H) = 0.95 Å for aromatic and 0.99 Å for CH2 H atoms, and with Uiso = 1.2Ueq (C). For the disordered O—H atoms d(O—H) = 0.84 Å, with Uiso = 1.5Ueq (O).
Compounds incorporating the thiazolidinone core structure are of great interest to chemists and biologists due to their extensive bioactivities (Shah & Desai, 2007). These include anti-microbial (Subudhi et al., 2007), anti-mycobacterial (Kuecuekguezel et al., 2006), anti-inflammatory (Srivastava et al., 2006), anti-fungal (Mehta et al., 2006) and anti-cancer effects (Zhou et al., 2008). In this context and following our on-going study of the synthesis of bio-selective molecules we were interested in investigating the microbial inhibiting effect of a newly synthesized series of compounds incorporating thiazolidinone ring systems. The synthesis of such compounds was carried out via a three component reaction technique using amino
as precursors (Mohamed et al., 2012). In this study, the determination of the title compound (I) was undertaken to investigate the relationship between its structure and anti-bacterial activity.The title compound (I), a phenylimino-thiazolidinone derivative, crystallizes with the S1/C1/C2/N1/C4 thiazole and C6···C11 phenyl rings inclined at 56.99 (6) ° to one another. The thiazole ring is planar with an r.m.s. deviation for the five ring atoms of 0.0274 Å. The C4═N5 distance, 1.2638 (19) Å, confirms this as a double bond and the molecule adopts a Z conformation with respect to this bond. The OH group of the hydroxyethyl substituent is disordered over two positions with relative occupancies 0.517 (4) for O2–H2 and 0.483 (4) for O3–H3. Bond distances (Allen et al., 1987) and angles in the molecule are normal and similar to those found in related structures (Bally & Mornon, 1973; Moghaddam & Hojabri, 2007; Yella et al., 2008; Abdel-Aziz et al., 2012).
In the π contacts further consolidate the structure forming stacks along b, Fig. 3.
head to tail dimers are formed from O2–H2···O1 hydrogen bonds, bolstered by weaker C1–H1B···N1 interactions, Table 1, forming R22(11) rings (Bernstein et al., 1995). These also link pairs of molecules into chains along b. Weak C12–H1B···S1 contacts join each chain to an equivalent one progressing in the opposite direction, Fig. 2. Two additional C–H···O hydrogen bonds together with C9–H9···For pharmaceutical background to thiazolidinone compounds, see: Shah & Desai (2007); Subudhi et al. (2007); Kuecuekguezel et al. (2006); Mehta et al. (2006); Srivastava et al. (2006); Zhou et al. (2008). For our recent work on the synthesis of bio-selective molecules, see: Mohamed et al. (2012). For related structures, see: Bally & Mornon (1973); Moghaddam & Hojabri (2007); Yella et al. (2008); Abdel-Aziz et al. (2012). For standard bond distances, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995).
Data collection: APEX2 (Bruker, 2011); cell
APEX2 and SAINT (Bruker, 2011); data reduction: SAINT (Bruker, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008) and TITAN (Hunter & Simpson, 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) and TITAN (Hunter & Simpson, 1999); molecular graphics: SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008), enCIFer (Allen et al., 2004), PLATON (Spek, 2009) and publCIF (Westrip, 2010).Fig. 1. The structure of I with ellipsoids drawn at the 50% probability level. Only the major disorder component is shown. | |
Fig. 2. A view of the packing along the a axis showing chains of molecules linked by C–H···S hydrogen bonds. Hydrogen bonds are drawn as dashed lines and only the major disorder component is shown. | |
Fig. 3. Overall packing for (1) viewed along the b axis showing a representative C–H···π contact as a dotted line. The red sphere represents the centroid of the C6···C11 phenyl ring. Hydrogen bonds are drawn as dashed lines and only the major disorder component is shown. |
C11H12N2O2S | F(000) = 496 |
Mr = 236.29 | Dx = 1.436 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 5327 reflections |
a = 11.9612 (6) Å | θ = 3.3–27.6° |
b = 6.9478 (3) Å | µ = 0.28 mm−1 |
c = 13.1554 (6) Å | T = 91 K |
β = 91.244 (2)° | Irregular block, yellow |
V = 1093.01 (9) Å3 | 0.40 × 0.26 × 0.11 mm |
Z = 4 |
Bruker APEXII CCD area-detector diffractometer | 2547 independent reflections |
Radiation source: fine-focus sealed tube | 2150 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.038 |
φ and ω scans | θmax = 27.7°, θmin = 3.1° |
Absorption correction: multi-scan (SADABS; Bruker, 2011) | h = −15→15 |
Tmin = 0.693, Tmax = 0.746 | k = −9→9 |
17811 measured reflections | l = −17→15 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.100 | H-atom parameters constrained |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0373P)2 + 0.9645P] where P = (Fo2 + 2Fc2)/3 |
2547 reflections | (Δ/σ)max < 0.001 |
157 parameters | Δρmax = 0.79 e Å−3 |
6 restraints | Δρmin = −0.68 e Å−3 |
C11H12N2O2S | V = 1093.01 (9) Å3 |
Mr = 236.29 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 11.9612 (6) Å | µ = 0.28 mm−1 |
b = 6.9478 (3) Å | T = 91 K |
c = 13.1554 (6) Å | 0.40 × 0.26 × 0.11 mm |
β = 91.244 (2)° |
Bruker APEXII CCD area-detector diffractometer | 2547 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2011) | 2150 reflections with I > 2σ(I) |
Tmin = 0.693, Tmax = 0.746 | Rint = 0.038 |
17811 measured reflections |
R[F2 > 2σ(F2)] = 0.041 | 6 restraints |
wR(F2) = 0.100 | H-atom parameters constrained |
S = 1.08 | Δρmax = 0.79 e Å−3 |
2547 reflections | Δρmin = −0.68 e Å−3 |
157 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
S1 | 0.27696 (4) | 0.19764 (7) | 0.90742 (4) | 0.02132 (14) | |
C1 | 0.18673 (18) | 0.0254 (3) | 0.96766 (16) | 0.0261 (4) | |
H1A | 0.1232 | −0.0083 | 0.9216 | 0.031* | |
H1B | 0.2287 | −0.0937 | 0.9843 | 0.031* | |
C2 | 0.14480 (17) | 0.1172 (3) | 1.06312 (15) | 0.0248 (4) | |
O1 | 0.08555 (15) | 0.0341 (2) | 1.12382 (12) | 0.0393 (4) | |
N1 | 0.17971 (13) | 0.3030 (2) | 1.07448 (12) | 0.0204 (3) | |
C4 | 0.24668 (14) | 0.3775 (3) | 0.99792 (13) | 0.0172 (4) | |
N5 | 0.28128 (12) | 0.5494 (2) | 1.00068 (11) | 0.0180 (3) | |
C6 | 0.34388 (14) | 0.6235 (3) | 0.91831 (14) | 0.0171 (4) | |
C7 | 0.29991 (15) | 0.6270 (3) | 0.81901 (14) | 0.0196 (4) | |
H7 | 0.2298 | 0.5682 | 0.8039 | 0.023* | |
C8 | 0.35896 (16) | 0.7167 (3) | 0.74242 (15) | 0.0213 (4) | |
H8 | 0.3292 | 0.7179 | 0.6749 | 0.026* | |
C9 | 0.46134 (17) | 0.8049 (3) | 0.76381 (15) | 0.0234 (4) | |
H9 | 0.5014 | 0.8661 | 0.7113 | 0.028* | |
C10 | 0.50430 (16) | 0.8025 (3) | 0.86274 (15) | 0.0233 (4) | |
H10 | 0.5742 | 0.8623 | 0.8777 | 0.028* | |
C11 | 0.44593 (15) | 0.7135 (3) | 0.94010 (14) | 0.0201 (4) | |
H11 | 0.4755 | 0.7139 | 1.0077 | 0.024* | |
C12 | 0.14901 (17) | 0.4171 (3) | 1.16360 (15) | 0.0255 (4) | |
H12A | 0.2113 | 0.5057 | 1.1812 | 0.031* | |
H12B | 0.1393 | 0.3292 | 1.2220 | 0.031* | |
C13 | 0.0447 (2) | 0.5319 (4) | 1.14846 (19) | 0.0439 (6) | |
H13A | −0.0167 | 0.4364 | 1.1469 | 0.053* | |
H13B | 0.0363 | 0.6054 | 1.2123 | 0.053* | |
O2 | 0.0188 (2) | 0.6593 (4) | 1.0724 (2) | 0.0241 (8) | 0.517 (4) |
H2 | 0.0483 | 0.7663 | 1.0856 | 0.036* | 0.517 (4) |
O3 | −0.0418 (2) | 0.4527 (5) | 1.1267 (2) | 0.0316 (9) | 0.483 (4) |
H3 | −0.0409 | 0.4168 | 1.0658 | 0.047* | 0.483 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0221 (2) | 0.0226 (3) | 0.0195 (2) | 0.00206 (18) | 0.00538 (17) | −0.00315 (18) |
C1 | 0.0326 (10) | 0.0206 (10) | 0.0254 (10) | −0.0003 (8) | 0.0066 (8) | −0.0018 (8) |
C2 | 0.0280 (10) | 0.0244 (10) | 0.0221 (10) | −0.0040 (8) | 0.0038 (8) | −0.0013 (8) |
O1 | 0.0548 (10) | 0.0346 (9) | 0.0292 (8) | −0.0195 (8) | 0.0170 (7) | −0.0056 (7) |
N1 | 0.0211 (8) | 0.0236 (8) | 0.0166 (8) | −0.0037 (6) | 0.0043 (6) | −0.0034 (6) |
C4 | 0.0140 (8) | 0.0230 (9) | 0.0146 (8) | 0.0029 (7) | −0.0001 (6) | −0.0010 (7) |
N5 | 0.0161 (7) | 0.0229 (8) | 0.0150 (7) | 0.0014 (6) | 0.0010 (6) | −0.0006 (6) |
C6 | 0.0181 (8) | 0.0163 (8) | 0.0170 (9) | 0.0037 (7) | 0.0029 (7) | −0.0007 (7) |
C7 | 0.0197 (8) | 0.0203 (9) | 0.0187 (9) | 0.0040 (7) | 0.0008 (7) | −0.0016 (7) |
C8 | 0.0280 (9) | 0.0186 (9) | 0.0172 (9) | 0.0058 (7) | 0.0014 (7) | 0.0014 (7) |
C9 | 0.0302 (10) | 0.0182 (9) | 0.0220 (10) | 0.0017 (8) | 0.0066 (8) | 0.0043 (8) |
C10 | 0.0221 (9) | 0.0205 (9) | 0.0272 (10) | −0.0028 (7) | 0.0018 (8) | 0.0020 (8) |
C11 | 0.0223 (9) | 0.0191 (9) | 0.0187 (9) | 0.0009 (7) | −0.0014 (7) | 0.0013 (7) |
C12 | 0.0322 (10) | 0.0290 (10) | 0.0157 (9) | −0.0098 (8) | 0.0084 (8) | −0.0067 (8) |
C13 | 0.0564 (10) | 0.0410 (10) | 0.0346 (9) | 0.0164 (8) | 0.0045 (8) | −0.0037 (8) |
O2 | 0.0295 (15) | 0.0209 (14) | 0.0217 (15) | −0.0021 (11) | −0.0001 (11) | −0.0017 (11) |
O3 | 0.0208 (15) | 0.054 (2) | 0.0197 (16) | 0.0020 (14) | 0.0030 (11) | −0.0044 (15) |
S1—C4 | 1.7689 (19) | C8—H8 | 0.9500 |
S1—C1 | 1.806 (2) | C9—C10 | 1.389 (3) |
C1—C2 | 1.504 (3) | C9—H9 | 0.9500 |
C1—H1A | 0.9900 | C10—C11 | 1.392 (3) |
C1—H1B | 0.9900 | C10—H10 | 0.9500 |
C2—O1 | 1.224 (2) | C11—H11 | 0.9500 |
C2—N1 | 1.364 (3) | C12—C13 | 1.490 (3) |
N1—C4 | 1.400 (2) | C12—H12A | 0.9900 |
N1—C12 | 1.469 (2) | C12—H12B | 0.9900 |
C4—N5 | 1.264 (2) | C13—O3 | 1.202 (4) |
N5—C6 | 1.427 (2) | C13—O2 | 1.367 (4) |
C6—C11 | 1.396 (3) | C13—H13A | 0.9900 |
C6—C7 | 1.398 (3) | C13—H13B | 0.9900 |
C7—C8 | 1.391 (3) | O2—H2 | 0.8400 |
C7—H7 | 0.9500 | O3—H3 | 0.8400 |
C8—C9 | 1.393 (3) | ||
C4—S1—C1 | 92.29 (9) | C10—C9—C8 | 119.34 (18) |
C2—C1—S1 | 107.38 (14) | C10—C9—H9 | 120.3 |
C2—C1—H1A | 110.2 | C8—C9—H9 | 120.3 |
S1—C1—H1A | 110.2 | C9—C10—C11 | 120.61 (18) |
C2—C1—H1B | 110.2 | C9—C10—H10 | 119.7 |
S1—C1—H1B | 110.2 | C11—C10—H10 | 119.7 |
H1A—C1—H1B | 108.5 | C10—C11—C6 | 119.96 (17) |
O1—C2—N1 | 123.72 (18) | C10—C11—H11 | 120.0 |
O1—C2—C1 | 123.58 (19) | C6—C11—H11 | 120.0 |
N1—C2—C1 | 112.69 (17) | N1—C12—C13 | 113.91 (18) |
C2—N1—C4 | 116.73 (16) | N1—C12—H12A | 108.8 |
C2—N1—C12 | 121.13 (16) | C13—C12—H12A | 108.8 |
C4—N1—C12 | 122.13 (16) | N1—C12—H12B | 108.8 |
N5—C4—N1 | 121.38 (16) | C13—C12—H12B | 108.8 |
N5—C4—S1 | 127.96 (14) | H12A—C12—H12B | 107.7 |
N1—C4—S1 | 110.59 (13) | O3—C13—O2 | 86.7 (3) |
C4—N5—C6 | 119.74 (16) | O3—C13—C12 | 120.0 (3) |
C11—C6—C7 | 119.60 (17) | O2—C13—C12 | 128.4 (2) |
C11—C6—N5 | 118.48 (16) | O2—C13—H13A | 105.2 |
C7—C6—N5 | 121.54 (16) | C12—C13—H13A | 105.2 |
C8—C7—C6 | 119.88 (17) | O3—C13—H13B | 109.6 |
C8—C7—H7 | 120.1 | O2—C13—H13B | 105.2 |
C6—C7—H7 | 120.1 | C12—C13—H13B | 105.2 |
C7—C8—C9 | 120.61 (18) | H13A—C13—H13B | 105.9 |
C7—C8—H8 | 119.7 | C13—O2—H2 | 109.5 |
C9—C8—H8 | 119.7 | C13—O3—H3 | 109.5 |
Cg2 is the centroid of the C6–C11 phenyl ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O1i | 0.84 | 1.98 | 2.802 (3) | 168 |
C13—H13B···O1ii | 0.99 | 2.67 | 3.407 (3) | 131 |
C1—H1A···O1iii | 0.99 | 2.56 | 3.472 (3) | 153 |
C12—H12B···S1iv | 0.99 | 2.92 | 3.613 (2) | 128 |
C1—H1B···N5v | 0.99 | 2.57 | 3.519 (3) | 162 |
C9—H9···Cg2vi | 0.95 | 2.77 | 3.5731 (16) | 142 |
Symmetry codes: (i) x, y+1, z; (ii) −x, y+1/2, −z+5/2; (iii) −x, −y, −z+2; (iv) x, −y+1/2, z+1/2; (v) x, y−1, z; (vi) −x+1, y−1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C11H12N2O2S |
Mr | 236.29 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 91 |
a, b, c (Å) | 11.9612 (6), 6.9478 (3), 13.1554 (6) |
β (°) | 91.244 (2) |
V (Å3) | 1093.01 (9) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.28 |
Crystal size (mm) | 0.40 × 0.26 × 0.11 |
Data collection | |
Diffractometer | Bruker APEXII CCD area-detector |
Absorption correction | Multi-scan (SADABS; Bruker, 2011) |
Tmin, Tmax | 0.693, 0.746 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 17811, 2547, 2150 |
Rint | 0.038 |
(sin θ/λ)max (Å−1) | 0.654 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.041, 0.100, 1.08 |
No. of reflections | 2547 |
No. of parameters | 157 |
No. of restraints | 6 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.79, −0.68 |
Computer programs: APEX2 (Bruker, 2011), APEX2 and SAINT (Bruker, 2011), SAINT (Bruker, 2011), SHELXS97 (Sheldrick, 2008) and TITAN (Hunter & Simpson, 1999), SHELXL97 (Sheldrick, 2008) and TITAN (Hunter & Simpson, 1999), SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2008), SHELXL97 (Sheldrick, 2008), enCIFer (Allen et al., 2004), PLATON (Spek, 2009) and publCIF (Westrip, 2010).
Cg2 is the centroid of the C6–C11 phenyl ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O1i | 0.84 | 1.98 | 2.802 (3) | 168 |
C13—H13B···O1ii | 0.99 | 2.67 | 3.407 (3) | 131 |
C1—H1A···O1iii | 0.99 | 2.56 | 3.472 (3) | 153 |
C12—H12B···S1iv | 0.99 | 2.92 | 3.613 (2) | 128 |
C1—H1B···N5v | 0.99 | 2.57 | 3.519 (3) | 162 |
C9—H9···Cg2vi | 0.95 | 2.77 | 3.5731 (16) | 142 |
Symmetry codes: (i) x, y+1, z; (ii) −x, y+1/2, −z+5/2; (iii) −x, −y, −z+2; (iv) x, −y+1/2, z+1/2; (v) x, y−1, z; (vi) −x+1, y−1/2, −z+1/2. |
Acknowledgements
The financial support of the Egyptian Higher Education authority is gratefully acknowledged. We extend also our thanks to Manchester Metropolitan University for supporting this study and the University of Otago for the purchase of the diffractometer.
References
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Compounds incorporating the thiazolidinone core structure are of great interest to chemists and biologists due to their extensive bioactivities (Shah & Desai, 2007). These include anti-microbial (Subudhi et al., 2007), anti-mycobacterial (Kuecuekguezel et al., 2006), anti-inflammatory (Srivastava et al., 2006), anti-fungal (Mehta et al., 2006) and anti-cancer effects (Zhou et al., 2008). In this context and following our on-going study of the synthesis of bio-selective molecules we were interested in investigating the microbial inhibiting effect of a newly synthesized series of compounds incorporating thiazolidinone ring systems. The synthesis of such compounds was carried out via a three component reaction technique using amino alcohols as precursors (Mohamed et al., 2012). In this study, the crystal structure determination of the title compound (I) was undertaken to investigate the relationship between its structure and anti-bacterial activity.
The title compound (I), a phenylimino-thiazolidinone derivative, crystallizes with the S1/C1/C2/N1/C4 thiazole and C6···C11 phenyl rings inclined at 56.99 (6) ° to one another. The thiazole ring is planar with an r.m.s. deviation for the five ring atoms of 0.0274 Å. The C4═N5 distance, 1.2638 (19) Å, confirms this as a double bond and the molecule adopts a Z conformation with respect to this bond. The OH group of the hydroxyethyl substituent is disordered over two positions with relative occupancies 0.517 (4) for O2–H2 and 0.483 (4) for O3–H3. Bond distances (Allen et al., 1987) and angles in the molecule are normal and similar to those found in related structures (Bally & Mornon, 1973; Moghaddam & Hojabri, 2007; Yella et al., 2008; Abdel-Aziz et al., 2012).
In the crystal structure head to tail dimers are formed from O2–H2···O1 hydrogen bonds, bolstered by weaker C1–H1B···N1 interactions, Table 1, forming R22(11) rings (Bernstein et al., 1995). These also link pairs of molecules into chains along b. Weak C12–H1B···S1 contacts join each chain to an equivalent one progressing in the opposite direction, Fig. 2. Two additional C–H···O hydrogen bonds together with C9–H9···π contacts further consolidate the structure forming stacks along b, Fig. 3.