organic compounds
Methyl 2-((2Z,5Z)-2-{(E)-2-[1-(4-hydroxyphenyl)ethylidene]hydrazin-1-ylidene}-4-oxo-3-phenyl-1,3-thiazolidin-5-ylidene)acetate
aChemistry and Environmental Division, Manchester Metropolitan University, Manchester, M1 5GD, England, bChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt, cDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA, dDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, and eKirkuk University, College of Science, Department of Chemistry, Kirkuk, Iraq
*Correspondence e-mail: shaabankamel@yahoo.com
In the title compound, C20H17N3O4S, all non-H atoms, except those of the phenyl ring, are approximately coplanar [maximum deviation = 0.2214 (1) Å], and the dihedral angle between their best plane and the benzene ring is 53.13 (1)°. A short intramolecular O⋯S contact of 2.838 (1) Å is formed between the ester carbonyl O atom and the S atom of the thiazolidine ring. In the crystal, molecules associated via O—H⋯O, C—H⋯O and C—H⋯S hydrogen bonds form layers parallel to (010), with only C—H⋯O-type short contacts between the molecules in adjacent layers.
CCDC reference: 960697
Related literature
For the biological activity of 4-thiazolidinones, see: Dayam et al. (2006); Srivastava et al. (2005), Look et al. (1996), Barreca et al. (2001); Diurno et al. (1992).
Experimental
Crystal data
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Data collection: APEX2 (Bruker, 2013); cell SAINT (Bruker, 2013); data reduction: SAINT; program(s) used to solve structure: SHELXT (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).
Supporting information
CCDC reference: 960697
10.1107/S1600536813025270/gk2589sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536813025270/gk2589Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536813025270/gk2589Isup3.cml
A mixture of 283 mg (1 mmol) (2Z)-2-[1-(4-methylphenyl)ethylidene]-N-phenylhydrazinecarbothioamide and 142 mg (1 mmol) dimethyl but-2-ynedioate in 50 ml of ethanol was refluxed and monitored by TLC until completion of the reaction. The excess solvent was evaporated under vacuum and the solid obtained was recrystallized from ethanol to afford clear yellow plates (M.p. 541–543 K) of X-ray quality.
The hydroxyl H atom was found from a difference Fourier map [O4—H4O = 0.84 (2) Å] and refined freely. H atoms bonded to C were placed in geometrically idealized positions and constrained to ride on their parent atoms C—H = 0.95 Å (aromatic H) and 0.98 Å (methyl H), with Uiso(H) = 1.5 Uiso(C) for methyl H atoms and Uiso(H) = 1.2 Uiso(C) for other H atoms.
Data collection: APEX2 (Bruker, 2013); cell
SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXT (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).Fig. 1. Perspective view of the title molecule with 50% probability displacement ellipsoids. | |
Fig. 2. View of the crystal packing down the a-axis showing the layer structure and O-H···O hydrogen bonding interactions as dotted lines. |
C20H17N3O4S | F(000) = 824 |
Mr = 395.42 | Dx = 1.385 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 8755 reflections |
a = 9.5049 (9) Å | θ = 2.3–28.6° |
b = 20.656 (2) Å | µ = 0.20 mm−1 |
c = 10.1364 (10) Å | T = 150 K |
β = 107.637 (1)° | Plate, clear yellow |
V = 1896.6 (3) Å3 | 0.19 × 0.11 × 0.05 mm |
Z = 4 |
Bruker SMART APEX CCD diffractometer | 4582 independent reflections |
Radiation source: fine-focus sealed tube | 3740 reflections with i > 2σ(i) |
Graphite monochromator | Rint = 0.039 |
Detector resolution: 8.3660 pixels mm-1 | θmax = 28.7°, θmin = 2.0° |
ϕ and ω scans | h = −12→12 |
Absorption correction: multi-scan (SADABS; Bruker, 2013) | k = −27→27 |
Tmin = 0.82, Tmax = 0.99 | l = −13→13 |
16907 measured reflections |
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)] = 0.044 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.118 | W = 1/[Σ2(FO2) + (0.0643P)2 + 0.3949P] WHERE P = (FO2 + 2FC2)/3 |
S = 1.06 | (Δ/σ)max = 0.001 |
4582 reflections | Δρmax = 0.34 e Å−3 |
259 parameters | Δρmin = −0.44 e Å−3 |
0 restraints |
C20H17N3O4S | V = 1896.6 (3) Å3 |
Mr = 395.42 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 9.5049 (9) Å | µ = 0.20 mm−1 |
b = 20.656 (2) Å | T = 150 K |
c = 10.1364 (10) Å | 0.19 × 0.11 × 0.05 mm |
β = 107.637 (1)° |
Bruker SMART APEX CCD diffractometer | 4582 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2013) | 3740 reflections with i > 2σ(i) |
Tmin = 0.82, Tmax = 0.99 | Rint = 0.039 |
16907 measured reflections |
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.118 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | Δρmax = 0.34 e Å−3 |
4582 reflections | Δρmin = −0.44 e Å−3 |
259 parameters |
Experimental. The diffraction data were collected in three sets of 606 frames (0.3° width in ω) at ϕ = 0, 120 and 240°. A scan time of 40 sec/frame was used. |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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 | ||
S1 | 1.01222 (4) | 0.18869 (2) | 0.39033 (4) | 0.0203 (1) | |
O1 | 1.40358 (11) | 0.26023 (5) | 0.52637 (11) | 0.0240 (3) | |
O2 | 1.09079 (13) | 0.05575 (6) | 0.42140 (13) | 0.0347 (4) | |
O3 | 1.32263 (14) | 0.02111 (6) | 0.52834 (14) | 0.0378 (4) | |
O4 | 0.14035 (12) | 0.15348 (6) | 0.10230 (13) | 0.0285 (3) | |
N1 | 1.16412 (13) | 0.29748 (6) | 0.43935 (12) | 0.0189 (3) | |
N2 | 0.90771 (13) | 0.31123 (6) | 0.34670 (13) | 0.0222 (4) | |
N3 | 0.77907 (13) | 0.27335 (6) | 0.30473 (13) | 0.0219 (4) | |
C1 | 1.27118 (16) | 0.25046 (7) | 0.47990 (15) | 0.0190 (4) | |
C2 | 1.20296 (16) | 0.18459 (7) | 0.45802 (14) | 0.0193 (4) | |
C3 | 1.01955 (15) | 0.27395 (7) | 0.38850 (14) | 0.0190 (4) | |
C4 | 1.28646 (17) | 0.13149 (7) | 0.49043 (16) | 0.0229 (4) | |
C5 | 1.22088 (18) | 0.06672 (8) | 0.47422 (16) | 0.0260 (5) | |
C6 | 1.2661 (3) | −0.04389 (9) | 0.5273 (3) | 0.0553 (8) | |
C7 | 1.20015 (15) | 0.36539 (7) | 0.44261 (16) | 0.0206 (4) | |
C8 | 1.29110 (17) | 0.39165 (8) | 0.56415 (17) | 0.0275 (5) | |
C9 | 1.3342 (2) | 0.45594 (9) | 0.5655 (2) | 0.0368 (5) | |
C10 | 1.2839 (2) | 0.49351 (8) | 0.4477 (2) | 0.0384 (6) | |
C11 | 1.1899 (2) | 0.46687 (8) | 0.32791 (19) | 0.0347 (5) | |
C12 | 1.14814 (18) | 0.40248 (8) | 0.32417 (16) | 0.0272 (5) | |
C13 | 0.65717 (16) | 0.30559 (7) | 0.27572 (15) | 0.0196 (4) | |
C14 | 0.64599 (17) | 0.37782 (8) | 0.28058 (17) | 0.0260 (5) | |
C15 | 0.52047 (15) | 0.26621 (7) | 0.23315 (15) | 0.0187 (4) | |
C16 | 0.52602 (16) | 0.19872 (7) | 0.23265 (17) | 0.0241 (4) | |
C17 | 0.39928 (17) | 0.16202 (8) | 0.18891 (18) | 0.0267 (5) | |
C18 | 0.26171 (16) | 0.19204 (7) | 0.14442 (15) | 0.0207 (4) | |
C19 | 0.25339 (16) | 0.25898 (7) | 0.14520 (16) | 0.0227 (4) | |
C20 | 0.38175 (16) | 0.29540 (7) | 0.18934 (16) | 0.0221 (4) | |
H4 | 1.39070 | 0.13580 | 0.52480 | 0.0270* | |
H4O | 0.066 (2) | 0.1774 (11) | 0.077 (2) | 0.046 (6)* | |
H6A | 1.19470 | −0.04490 | 0.57960 | 0.0830* | |
H6B | 1.34780 | −0.07350 | 0.56990 | 0.0830* | |
H6C | 1.21740 | −0.05730 | 0.43150 | 0.0830* | |
H8 | 1.32360 | 0.36600 | 0.64560 | 0.0330* | |
H9 | 1.39860 | 0.47420 | 0.64770 | 0.0440* | |
H10 | 1.31370 | 0.53750 | 0.44900 | 0.0460* | |
H11 | 1.15380 | 0.49300 | 0.24760 | 0.0420* | |
H12 | 1.08480 | 0.38410 | 0.24160 | 0.0330* | |
H14A | 0.74530 | 0.39660 | 0.31100 | 0.0390* | |
H14B | 0.59250 | 0.38990 | 0.34570 | 0.0390* | |
H14C | 0.59280 | 0.39420 | 0.18820 | 0.0390* | |
H16 | 0.61910 | 0.17760 | 0.26310 | 0.0290* | |
H17 | 0.40570 | 0.11610 | 0.18910 | 0.0320* | |
H19 | 0.16000 | 0.27990 | 0.11560 | 0.0270* | |
H20 | 0.37500 | 0.34130 | 0.18970 | 0.0260* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0149 (2) | 0.0209 (2) | 0.0233 (2) | −0.0034 (1) | 0.0030 (1) | −0.0019 (1) |
O1 | 0.0134 (5) | 0.0242 (6) | 0.0308 (6) | −0.0009 (4) | 0.0011 (4) | 0.0019 (4) |
O2 | 0.0316 (7) | 0.0275 (6) | 0.0427 (7) | −0.0071 (5) | 0.0078 (5) | −0.0030 (5) |
O3 | 0.0387 (7) | 0.0198 (6) | 0.0525 (8) | 0.0051 (5) | 0.0104 (6) | 0.0035 (5) |
O4 | 0.0159 (5) | 0.0239 (6) | 0.0441 (7) | −0.0016 (5) | 0.0067 (5) | −0.0074 (5) |
N1 | 0.0131 (6) | 0.0191 (6) | 0.0222 (6) | −0.0025 (5) | 0.0017 (5) | −0.0002 (5) |
N2 | 0.0141 (6) | 0.0247 (7) | 0.0252 (7) | −0.0007 (5) | 0.0022 (5) | −0.0009 (5) |
N3 | 0.0137 (6) | 0.0252 (7) | 0.0250 (7) | −0.0005 (5) | 0.0030 (5) | 0.0008 (5) |
C1 | 0.0158 (7) | 0.0215 (7) | 0.0187 (7) | −0.0012 (5) | 0.0036 (5) | 0.0005 (5) |
C2 | 0.0180 (7) | 0.0220 (7) | 0.0172 (7) | −0.0034 (6) | 0.0043 (5) | −0.0011 (5) |
C3 | 0.0147 (7) | 0.0220 (7) | 0.0186 (7) | −0.0026 (5) | 0.0025 (5) | −0.0012 (5) |
C4 | 0.0193 (7) | 0.0236 (8) | 0.0242 (7) | 0.0000 (6) | 0.0044 (6) | −0.0009 (6) |
C5 | 0.0294 (8) | 0.0222 (8) | 0.0273 (8) | 0.0005 (6) | 0.0101 (7) | −0.0014 (6) |
C6 | 0.0658 (15) | 0.0195 (9) | 0.0817 (17) | 0.0013 (9) | 0.0238 (13) | 0.0051 (10) |
C7 | 0.0153 (6) | 0.0181 (7) | 0.0273 (8) | −0.0001 (5) | 0.0050 (6) | −0.0002 (6) |
C8 | 0.0230 (8) | 0.0242 (8) | 0.0296 (8) | 0.0001 (6) | −0.0005 (6) | 0.0014 (6) |
C9 | 0.0334 (9) | 0.0251 (9) | 0.0423 (10) | −0.0044 (7) | −0.0031 (8) | −0.0061 (7) |
C10 | 0.0401 (10) | 0.0182 (8) | 0.0524 (12) | −0.0038 (7) | 0.0071 (9) | 0.0001 (7) |
C11 | 0.0408 (10) | 0.0246 (8) | 0.0354 (9) | 0.0018 (7) | 0.0066 (8) | 0.0074 (7) |
C12 | 0.0283 (8) | 0.0242 (8) | 0.0251 (8) | −0.0008 (6) | 0.0023 (6) | −0.0004 (6) |
C13 | 0.0157 (7) | 0.0239 (8) | 0.0185 (7) | 0.0017 (6) | 0.0041 (5) | 0.0016 (5) |
C14 | 0.0198 (7) | 0.0224 (8) | 0.0344 (9) | 0.0006 (6) | 0.0060 (6) | −0.0006 (6) |
C15 | 0.0143 (7) | 0.0228 (7) | 0.0190 (7) | 0.0009 (5) | 0.0051 (5) | 0.0017 (5) |
C16 | 0.0151 (7) | 0.0232 (8) | 0.0334 (8) | 0.0042 (6) | 0.0065 (6) | 0.0029 (6) |
C17 | 0.0206 (8) | 0.0191 (7) | 0.0409 (9) | 0.0027 (6) | 0.0099 (7) | −0.0003 (6) |
C18 | 0.0162 (7) | 0.0234 (8) | 0.0230 (7) | −0.0013 (6) | 0.0069 (6) | −0.0028 (6) |
C19 | 0.0147 (7) | 0.0249 (8) | 0.0270 (8) | 0.0044 (6) | 0.0041 (6) | 0.0003 (6) |
C20 | 0.0171 (7) | 0.0195 (7) | 0.0289 (8) | 0.0032 (6) | 0.0059 (6) | 0.0015 (6) |
S1—C2 | 1.7352 (16) | C13—C15 | 1.482 (2) |
S1—C3 | 1.7628 (15) | C15—C20 | 1.394 (2) |
O1—C1 | 1.2195 (19) | C15—C16 | 1.395 (2) |
O2—C5 | 1.211 (2) | C16—C17 | 1.378 (2) |
O3—C5 | 1.343 (2) | C17—C18 | 1.393 (2) |
O3—C6 | 1.445 (2) | C18—C19 | 1.385 (2) |
O4—C18 | 1.360 (2) | C19—C20 | 1.387 (2) |
O4—H4O | 0.84 (2) | C4—H4 | 0.9500 |
N1—C1 | 1.376 (2) | C6—H6A | 0.9800 |
N1—C7 | 1.4420 (19) | C6—H6B | 0.9800 |
N1—C3 | 1.4003 (19) | C6—H6C | 0.9800 |
N2—N3 | 1.4046 (18) | C8—H8 | 0.9500 |
N2—C3 | 1.2766 (19) | C9—H9 | 0.9500 |
N3—C13 | 1.291 (2) | C10—H10 | 0.9500 |
C1—C2 | 1.495 (2) | C11—H11 | 0.9500 |
C2—C4 | 1.335 (2) | C12—H12 | 0.9500 |
C4—C5 | 1.464 (2) | C14—H14A | 0.9800 |
C7—C12 | 1.383 (2) | C14—H14B | 0.9800 |
C7—C8 | 1.384 (2) | C14—H14C | 0.9800 |
C8—C9 | 1.389 (3) | C16—H16 | 0.9500 |
C9—C10 | 1.382 (3) | C17—H17 | 0.9500 |
C10—C11 | 1.385 (3) | C19—H19 | 0.9500 |
C11—C12 | 1.385 (2) | C20—H20 | 0.9500 |
C13—C14 | 1.498 (2) | ||
C2—S1—C3 | 90.75 (7) | O4—C18—C17 | 117.69 (13) |
C5—O3—C6 | 115.39 (17) | O4—C18—C19 | 122.83 (14) |
C18—O4—H4O | 107.9 (15) | C17—C18—C19 | 119.48 (14) |
C1—N1—C3 | 114.79 (12) | C18—C19—C20 | 119.81 (14) |
C3—N1—C7 | 123.08 (12) | C15—C20—C19 | 121.51 (13) |
C1—N1—C7 | 122.05 (13) | C2—C4—H4 | 119.00 |
N3—N2—C3 | 108.99 (12) | C5—C4—H4 | 119.00 |
N2—N3—C13 | 114.87 (12) | O3—C6—H6A | 109.00 |
O1—C1—C2 | 123.95 (14) | O3—C6—H6B | 109.00 |
N1—C1—C2 | 110.48 (13) | O3—C6—H6C | 109.00 |
O1—C1—N1 | 125.57 (14) | H6A—C6—H6B | 110.00 |
S1—C2—C4 | 127.54 (12) | H6A—C6—H6C | 109.00 |
C1—C2—C4 | 120.83 (14) | H6B—C6—H6C | 109.00 |
S1—C2—C1 | 111.63 (11) | C7—C8—H8 | 120.00 |
S1—C3—N2 | 125.07 (12) | C9—C8—H8 | 120.00 |
N1—C3—N2 | 122.57 (13) | C8—C9—H9 | 120.00 |
S1—C3—N1 | 112.36 (10) | C10—C9—H9 | 120.00 |
C2—C4—C5 | 121.46 (15) | C9—C10—H10 | 120.00 |
O2—C5—O3 | 124.20 (16) | C11—C10—H10 | 120.00 |
O2—C5—C4 | 124.31 (15) | C10—C11—H11 | 120.00 |
O3—C5—C4 | 111.46 (14) | C12—C11—H11 | 120.00 |
N1—C7—C12 | 119.94 (14) | C7—C12—H12 | 121.00 |
C8—C7—C12 | 121.22 (14) | C11—C12—H12 | 121.00 |
N1—C7—C8 | 118.80 (13) | C13—C14—H14A | 109.00 |
C7—C8—C9 | 119.12 (15) | C13—C14—H14B | 109.00 |
C8—C9—C10 | 120.31 (17) | C13—C14—H14C | 109.00 |
C9—C10—C11 | 119.78 (16) | H14A—C14—H14B | 110.00 |
C10—C11—C12 | 120.59 (16) | H14A—C14—H14C | 109.00 |
C7—C12—C11 | 118.95 (15) | H14B—C14—H14C | 109.00 |
N3—C13—C15 | 115.50 (13) | C15—C16—H16 | 119.00 |
C14—C13—C15 | 119.45 (13) | C17—C16—H16 | 119.00 |
N3—C13—C14 | 125.05 (14) | C16—C17—H17 | 120.00 |
C13—C15—C20 | 121.09 (13) | C18—C17—H17 | 120.00 |
C16—C15—C20 | 117.65 (14) | C18—C19—H19 | 120.00 |
C13—C15—C16 | 121.25 (14) | C20—C19—H19 | 120.00 |
C15—C16—C17 | 121.37 (15) | C15—C20—H20 | 119.00 |
C16—C17—C18 | 120.18 (15) | C19—C20—H20 | 119.00 |
C3—S1—C2—C1 | 0.49 (11) | S1—C2—C4—C5 | −1.6 (2) |
C3—S1—C2—C4 | 179.93 (14) | C1—C2—C4—C5 | 177.79 (14) |
C2—S1—C3—N1 | −0.41 (11) | C2—C4—C5—O2 | 6.1 (3) |
C2—S1—C3—N2 | 179.83 (13) | C2—C4—C5—O3 | −172.43 (14) |
C6—O3—C5—O2 | −3.4 (3) | N1—C7—C8—C9 | 175.77 (15) |
C6—O3—C5—C4 | 175.15 (17) | C12—C7—C8—C9 | −2.0 (3) |
C3—N1—C1—O1 | 179.63 (14) | N1—C7—C12—C11 | −176.95 (15) |
C3—N1—C1—C2 | 0.14 (17) | C8—C7—C12—C11 | 0.8 (3) |
C7—N1—C1—O1 | 2.8 (2) | C7—C8—C9—C10 | 1.5 (3) |
C7—N1—C1—C2 | −176.72 (12) | C8—C9—C10—C11 | 0.1 (3) |
C1—N1—C3—S1 | 0.22 (15) | C9—C10—C11—C12 | −1.3 (3) |
C1—N1—C3—N2 | 179.98 (14) | C10—C11—C12—C7 | 0.9 (3) |
C7—N1—C3—S1 | 177.05 (11) | N3—C13—C15—C16 | 3.4 (2) |
C7—N1—C3—N2 | −3.2 (2) | N3—C13—C15—C20 | −175.24 (14) |
C1—N1—C7—C8 | −52.6 (2) | C14—C13—C15—C16 | −177.37 (14) |
C1—N1—C7—C12 | 125.14 (16) | C14—C13—C15—C20 | 4.0 (2) |
C3—N1—C7—C8 | 130.78 (15) | C13—C15—C16—C17 | −177.90 (15) |
C3—N1—C7—C12 | −51.5 (2) | C20—C15—C16—C17 | 0.8 (2) |
C3—N2—N3—C13 | 172.11 (13) | C13—C15—C20—C19 | 177.96 (14) |
N3—N2—C3—S1 | 0.83 (17) | C16—C15—C20—C19 | −0.7 (2) |
N3—N2—C3—N1 | −178.90 (12) | C15—C16—C17—C18 | −0.3 (3) |
N2—N3—C13—C14 | 1.6 (2) | C16—C17—C18—O4 | 179.96 (15) |
N2—N3—C13—C15 | −179.18 (12) | C16—C17—C18—C19 | −0.3 (2) |
O1—C1—C2—S1 | −179.96 (13) | O4—C18—C19—C20 | −179.92 (14) |
O1—C1—C2—C4 | 0.6 (2) | C17—C18—C19—C20 | 0.4 (2) |
N1—C1—C2—S1 | −0.45 (15) | C18—C19—C20—C15 | 0.1 (2) |
N1—C1—C2—C4 | −179.95 (15) |
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4O···O1i | 0.84 (2) | 1.96 (2) | 2.7901 (16) | 174.8 (19) |
C8—H8···S1ii | 0.95 | 2.82 | 3.7272 (17) | 160 |
C10—H10···O4iii | 0.95 | 2.52 | 3.452 (2) | 167 |
C14—H14A···N2 | 0.98 | 2.30 | 2.742 (2) | 106 |
C19—H19···O1i | 0.95 | 2.47 | 3.200 (2) | 133 |
Symmetry codes: (i) x−3/2, −y+1/2, z−1/2; (ii) x+1/2, −y+1/2, z+1/2; (iii) −x+3/2, y+1/2, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4O···O1i | 0.84 (2) | 1.96 (2) | 2.7901 (16) | 174.8 (19) |
C8—H8···S1ii | 0.95 | 2.82 | 3.7272 (17) | 160 |
C10—H10···O4iii | 0.95 | 2.52 | 3.452 (2) | 167 |
C19—H19···O1i | 0.95 | 2.47 | 3.200 (2) | 133 |
Symmetry codes: (i) x−3/2, −y+1/2, z−1/2; (ii) x+1/2, −y+1/2, z+1/2; (iii) −x+3/2, y+1/2, −z+1/2. |
Acknowledgements
Manchester Metropolitan University, Tulane University and Erciyes University are gratefully acknowledged for supporting this study.
References
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Thiazolidinone scaffold compounds have received much attention from organic and medicinal chemists due to their therapeutic diversity coupled with their commercial viability. Recently, 4-thiazolidinones have exhibited many interesting bio-activity profiles such as anti-cancer (Dayam et al., 2006) and anti-mycobacterial agents (Srivastava et al., 2005), COX-1 inhibitors (Look et al. 1996), non-nucleoside inhibitors of HIV-RT (Barreca et al., 2001) and anti-histaminic agents (Diurno et al., 1992). In view of these properties the title compound has been synthesized among a series of other 4-thiazolidinones to investigate the relationship between their crystal structures and their antibacterial activity.
In the title compound (Fig. 1), all non-H atoms, except the phenyl group (C7–C12), are approximately coplanar, with the maximum deviations of -0.2214 (1) Å for C6, -0.2097 (1) Å for C14, 0.1651 (1) Å for O2 and -0.1009 (1) Å for O3, and the benzene ring (C7–C12) makes a dihedral angle of 53.13 (1)° with this plane. Molecular conformation is stabilized by a short intramolecular O···S contact of 2.838 (1) Å.
The title compound crystallizes in a layer structure with the layers parallel to the (010) plane (Fig. 2). Molecules within the layers are associated via O—H···O, C—H···O and C—H···S hydrogen bonding (Table 1, Fig. 2). One of the C—H···O contacts (C10—H10···O4) in Table 1 is between the layers. The interlayer regions are occupied by the N-phenyl and ester groups between which there are no significant interactions.