Alaa A. Hassan

Barreca

Dayam

Diurno

Farrugia

Joel T. Mague

Look

Mehmet Akkurt

Mustafa R. Albayati

Shaaban K. Mohamed

Sheldrick

Spek

Srivastava

Acta Crystallographica Section E

Crossref

Methyl 2-((2Z,5Z)-2-{(E)-2-[1-(4-hydroxy-phenyl)ethylidene]hydrazin-1-ylidene}-4-oxo-3-phenyl-1,3-thiazolidin-5-ylidene)-acetateShaaban K. Mohamed,a,b Joel T. Mague,c Mehmet Akkurt,dAlaa A. Hassanb and Mustafa R. Albayatie*aChemistry and Environmental Division, Manchester Metropolitan University,Manchester, M1 5GD, England, bChemistry Department, Faculty of Science, MiniaUniversity, 61519 El-Minia, Egypt, cDepartment of Chemistry, Tulane University,New Orleans, LA 70118, USA, dDepartment of Physics, Faculty of Sciences, ErciyesUniversity, 38039 Kayseri, Turkey, and eKirkuk University, College of Science,Department of Chemistry, Kirkuk, IraqCorrespondence e-mail: shaabankamel@yahoo.comReceived 29 July 2013; accepted 11 September 2013Key indicators: single-crystal X-ray study; T = 150 K; mean (C–C) = 0.002 A˚;R factor = 0.044; wR factor = 0.118; data-to-parameter ratio = 17.7.In the title compound, C20H17N3O4S, all non-H atoms, exceptthose of the phenyl ring, are approximately coplanar[maximum deviation = 0.2214 (1) A˚], and the dihedral anglebetween their best plane and the benzene ring is 53.13 (1). Ashort intramolecular O  S contact of 2.838 (1) A˚ is formedbetween the ester carbonyl O atom and the S atom of thethiazolidine ring. In the crystal, molecules associated via O—H  O, C—H  O and C—H  S hydrogen bonds form layersparallel to (010), with only C—H  O-type short contactsbetween the molecules in adjacent layers.Related literatureFor the biological activity of 4-thiazolidinones, see: Dayam etal. (2006); Srivastava et al. (2005), Look et al. (1996), Barrecaet al. (2001); Diurno et al. (1992).ExperimentalCrystal dataC20H17N3O4SMr = 395.42Monoclinic, P21=na = 9.5049 (9) A˚b = 20.656 (2) A˚c = 10.1364 (10) A˚ = 107.637 (1)V = 1896.6 (3) A˚3Z = 4Mo K radiation = 0.20 mm1T = 150 K0.19  0.11  0.05 mmData collectionBruker SMART APEX CCDdiffractometerAbsorption correction: multi-scan(SADABS; Bruker, 2013)Tmin = 0.82, Tmax = 0.9916907 measured reflections4582 independent reflections3740 reflections with i > 2(i)Rint = 0.039RefinementR[F 2 > 2(F 2)] = 0.044wR(F 2) = 0.118S = 1.064582 reflections259 parametersH atoms treated by a mixture ofindependent and constrainedrefinementmax = 0.34 e A˚3min = 0.44 e A˚3Table 1Hydrogen-bond geometry (A˚, ).D—H  A D—H H  A D  A D—H  AO4—H4O  O1i 0.84 (2) 1.96 (2) 2.7901 (16) 174.8 (19)C8—H8  S1ii 0.95 2.82 3.7272 (17) 160C10—H10  O4iii 0.95 2.52 3.452 (2) 167C19—H19  O1i 0.95 2.47 3.200 (2) 133Symmetry codes: (i) x 32;yþ 12; z  12; (ii) xþ 12;yþ 12; zþ 12; (iii)x þ 32; yþ 12;zþ 12.Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT(Bruker, 2013); data reduction: SAINT; program(s) used to solvestructure: SHELXT (Sheldrick, 2008); program(s) used to refinestructure: SHELXL2013 (Sheldrick, 2008); molecular graphics:ORTEP-3 for Windows (Farrugia, 2012); software used to preparematerial for publication: WinGX (Farrugia, 2012) and PLATON(Spek, 2009).Manchester Metropolitan University, Tulane University andErciyes University are gratefully acknowledged for supportingthis study.Supplementary data and figures for this paper are available from theIUCr electronic archives (Reference: GK2589).ReferencesBarreca, M. L., Chimirri, A., Luca, L. D., Monforte, A., Monforte, P., Rao, A.,Zappala, M., Balzarini, J., De Clercq, E., Pannecouque, C. & Witvrouw, M.(2001). Bioorg. Med. Chem. Lett. pp. 1793–1796.Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison,Wisconsin, USA.Dayam, R., Aiello, F., Deng, J., Wu, Y., Garofalo, A., Chen, X. & Neamati, N.(2006). J. Med. Chem. 49, 4526–4534.Diurno, M. V., Mazzoni, O., Calignano, P. E., Giordano, F. & Bolognese, A.(1992). J. Med. Chem. 35, 2910–2912.Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.organic compoundsActa Cryst. (2013). E69, o1553–o1554 doi:10.1107/S1600536813025270 Mohamed et al. o1553Acta Crystallographica Section EStructure ReportsOnlineISSN 1600-5368Look, G. C., Schullek, J. R., Homes, C. P., Chinn, J. P., Gordon, E. M. & Gallop,M. A. (1996). Bioorg. Med. Chem. Lett. 6, 707–712.Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.Spek, A. L. (2009). Acta Cryst. D65, 148–155.Srivastava, T., Gaikwad, A. K., Haq, W., Sinha, S. & Katti, S. B. (2005).ARKIVOC, ii, 120–130.organic compoundso1554 Mohamed et al.  C20H17N3O4S Acta Cryst. (2013). E69, o1553–o1554supporting informationsup-1Acta Cryst. (2013). E69, o1553–o1554    supporting informationActa Cryst. (2013). E69, o1553–o1554    [doi:10.1107/S1600536813025270]Methyl 2-((2Z,5Z)-2-{(E)-2-[1-(4-hydroxyphenyl)ethylidene]hydrazin-1-yl-idene}-4-oxo-3-phenyl-1,3-thiazolidin-5-ylidene)acetateShaaban K. Mohamed, Joel T. Mague, Mehmet Akkurt, Alaa A. Hassan and Mustafa R. AlbayatiS1. Comment 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.S2. Experimental 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.S3. Refinement 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.supporting informationsup-2Acta Cryst. (2013). E69, o1553–o1554    Figure 1Perspective view of the title molecule with 50% probability displacement ellipsoids. Figure 2View of the crystal packing down the a-axis showing the layer structure and O-H···O hydrogen bonding interactions as dotted lines. supporting informationsup-3Acta Cryst. (2013). E69, o1553–o1554    Methyl 2-((2Z,5Z)-2-{(E)-2-[1-(4-hydroxyphenyl)ethylidene]hydrazin-1-ylidene}-4-oxo-3-phenyl-1,3-thiazolidin-5-ylidene)acetate Crystal data C20H17N3O4SMr = 395.42Monoclinic, P21/nHall symbol: -P 2yna = 9.5049 (9) Åb = 20.656 (2) Åc = 10.1364 (10) Åβ = 107.637 (1)°V = 1896.6 (3) Å3Z = 4F(000) = 824Dx = 1.385 Mg m−3Mo Kα radiation, λ = 0.71073 ÅCell parameters from 8755 reflectionsθ = 2.3–28.6°µ = 0.20 mm−1T = 150 KPlate, clear yellow0.19 × 0.11 × 0.05 mmData collection Bruker SMART APEX CCD diffractometerRadiation source: fine-focus sealed tubeGraphite monochromatorDetector resolution: 8.3660 pixels mm-1φ and ω scansAbsorption correction: multi-scan (SADABS; Bruker, 2013)Tmin = 0.82, Tmax = 0.9916907 measured reflections4582 independent reflections3740 reflections with i > 2σ(i)Rint = 0.039θmax = 28.7°, θmin = 2.0°h = −12→12k = −27→27l = −13→13Refinement Refinement on F2Least-squares matrix: fullR[F2 > 2σ(F2)] = 0.044wR(F2) = 0.118S = 1.064582 reflections259 parameters0 restraintsPrimary atom site location: structure-invariant direct methodsSecondary atom site location: difference Fourier mapH atoms treated by a mixture of independent and constrained refinementW = 1/[Σ2(FO2) + (0.0643P)2 + 0.3949P] WHERE P = (FO2 + 2FC2)/3(Δ/σ)max = 0.001Δρmax = 0.34 e Å−3Δρmin = −0.44 e Å−3Special details 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 anglesRefinement. 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.Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) x y z Uiso*/UeqS1 1.01222 (4) 0.18869 (2) 0.39033 (4) 0.0203 (1)supporting informationsup-4Acta Cryst. (2013). E69, o1553–o1554    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*supporting informationsup-5Acta Cryst. (2013). E69, o1553–o1554    Atomic displacement parameters (Å2) U11 U22 U33 U12 U13 U23S1 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)Geometric parameters (Å, º) 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 0.9500N1—C1 1.376 (2) C6—H6A 0.9800N1—C7 1.4420 (19) C6—H6B 0.9800N1—C3 1.4003 (19) C6—H6C 0.9800N2—N3 1.4046 (18) C8—H8 0.9500N2—C3 1.2766 (19) C9—H9 0.9500N3—C13 1.291 (2) C10—H10 0.9500supporting informationsup-6Acta Cryst. (2013). E69, o1553–o1554    C1—C2 1.495 (2) C11—H11 0.9500C2—C4 1.335 (2) C12—H12 0.9500C4—C5 1.464 (2) C14—H14A 0.9800C7—C12 1.383 (2) C14—H14B 0.9800C7—C8 1.384 (2) C14—H14C 0.9800C8—C9 1.389 (3) C16—H16 0.9500C9—C10 1.382 (3) C17—H17 0.9500C10—C11 1.385 (3) C19—H19 0.9500C11—C12 1.385 (2) C20—H20 0.9500C13—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 119.00N3—N2—C3 108.99 (12) C5—C4—H4 119.00N2—N3—C13 114.87 (12) O3—C6—H6A 109.00O1—C1—C2 123.95 (14) O3—C6—H6B 109.00N1—C1—C2 110.48 (13) O3—C6—H6C 109.00O1—C1—N1 125.57 (14) H6A—C6—H6B 110.00S1—C2—C4 127.54 (12) H6A—C6—H6C 109.00C1—C2—C4 120.83 (14) H6B—C6—H6C 109.00S1—C2—C1 111.63 (11) C7—C8—H8 120.00S1—C3—N2 125.07 (12) C9—C8—H8 120.00N1—C3—N2 122.57 (13) C8—C9—H9 120.00S1—C3—N1 112.36 (10) C10—C9—H9 120.00C2—C4—C5 121.46 (15) C9—C10—H10 120.00O2—C5—O3 124.20 (16) C11—C10—H10 120.00O2—C5—C4 124.31 (15) C10—C11—H11 120.00O3—C5—C4 111.46 (14) C12—C11—H11 120.00N1—C7—C12 119.94 (14) C7—C12—H12 121.00C8—C7—C12 121.22 (14) C11—C12—H12 121.00N1—C7—C8 118.80 (13) C13—C14—H14A 109.00C7—C8—C9 119.12 (15) C13—C14—H14B 109.00C8—C9—C10 120.31 (17) C13—C14—H14C 109.00C9—C10—C11 119.78 (16) H14A—C14—H14B 110.00C10—C11—C12 120.59 (16) H14A—C14—H14C 109.00C7—C12—C11 118.95 (15) H14B—C14—H14C 109.00N3—C13—C15 115.50 (13) C15—C16—H16 119.00C14—C13—C15 119.45 (13) C17—C16—H16 119.00N3—C13—C14 125.05 (14) C16—C17—H17 120.00C13—C15—C20 121.09 (13) C18—C17—H17 120.00C16—C15—C20 117.65 (14) C18—C19—H19 120.00C13—C15—C16 121.25 (14) C20—C19—H19 120.00C15—C16—C17 121.37 (15) C15—C20—H20 119.00C16—C17—C18 120.18 (15) C19—C20—H20 119.00supporting informationsup-7Acta Cryst. (2013). E69, o1553–o1554    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)Hydrogen-bond geometry (Å, º) D—H···A D—H H···A D···A D—H···AO4—H4O···O1i 0.84 (2) 1.96 (2) 2.7901 (16) 174.8 (19)C8—H8···S1ii 0.95 2.82 3.7272 (17) 160C10—H10···O4iii 0.95 2.52 3.452 (2) 167C14—H14A···N2 0.98 2.30 2.742 (2) 106C19—H19···O1i 0.95 2.47 3.200 (2) 133Symmetry 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.

Acta Crystallographica Section E Structure Reports Online

Methyl 2-((2Z,5Z)-2-{(E)-2-[1-(4-hydroxyphenyl)ethylidene]hydrazin-1-ylidene}-4-oxo-3-phenyl-1,3-thiazolidin-5-ylidene)acetate

http://journals.iucr.org/e/issues/2013/10/00/gk2589/gk2589.pdf

Methyl 2-((2
                    Z

Methyl 2-((2 Z

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