Altomare

Bharti

Bhimashankar M. Halasangi

Farrugia

G. N. Anil Kumar

Kondratieva

Nardelli

Prema S. Badami

Sadık

Sangamesh A. Patil

Sheldrick

Spek

Acta Crystallographica Section E

In the title molecule, C17H12N4OS, the thiazole ring forms a dihedral angle of 10.8 (2)° with the phenyl ring and an angle of 3.1 (3)° with the indole ring system [which has a maximum deviation of 0.035 (2) Å]. The dihedral angle between the planes of the phenyl ring and the indole ring system is 11.5 (1)°. An intramolecular N—H...O hydrogen bond is observed. In the crystal, pairs of N—H...O hydrogen bonds form inversion dimers with anR22(8) graph-set motif.</jats:p

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Crystal structure of 3-[(E)-2-(4-phenyl-1,3-thiazol-2-yl)hydrazin-1-ylidene]-indolin-2-oneBhimashankar M. Halasangi,a Prema S. Badami,bSangamesh A. Patila and G. N. Anil Kumarc*aDepartment of Chemistry, Karnatak University, Dharwad, India, bDepartment ofChemistry, Shri Sharanabasaveshwar College of Science, Gulbarga 585 102, India,and cDepartment of Physics, M S Ramaiah Institute of Technology, Bangalore560 054, Karnataka, India. *Correspondence e-mail: anilgn@msrit.eduReceived 4 October 2014; accepted 16 October 2014Edited by A. J. Lough, University of Toronto, CanadaIn the title molecule, C17H12N4OS, the thiazole ring forms adihedral angle of 10.8 (2) with the phenyl ring and an angle of3.1 (3) with the indole ring system [which has a maximumdeviation of 0.035 (2) A˚]. The dihedral angle between theplanes of the phenyl ring and the indole ring system is11.5 (1). An intramolecular N—H  O hydrogen bond isobserved. In the crystal, pairs of N—H  O hydrogen bondsform inversion dimers with an R22(8) graph-set motif.Keywords: crystal structure; indolinone; hydrazine; 1,3-thiazole;hydrogen bonding; biological activity.CCDC reference: 10294981. Related literatureFor the biological activities of substituted thiazoles, see: Ali etal. (2011); Bharti et al. (2010); Kondratieva et al. (2007). For arelated structure, see: Sadık et al. (2004).2. Experimental2.1. Crystal dataC17H12N4OSMr = 320.37Monoclinic, P21=ca = 17.7108 (8) A˚b = 5.1411 (2) A˚c = 15.9065 (6) A˚ = 94.706 (3)V = 1443.45 (10) A˚3Z = 4Mo K radiation = 0.23 mm1T = 296 K0.35  0.31  0.25 mm2.2. Data collectionBruker SMART CCD area-detectordiffractometerAbsorption correction: multi-scan(SADABS; Sheldrick, 1996)Tmin = 0.887, Tmax = 0.93411530 measured reflections3142 independent reflections2124 reflections with I > 2(I)Rint = 0.0392.3. RefinementR[F 2 > 2(F 2)] = 0.046wR(F 2) = 0.109S = 1.093142 reflections208 parametersH-atom parameters constrainedmax = 0.20 e A˚3min = 0.25 e A˚3Table 1Hydrogen-bond geometry (A˚, ).D—H  A D—H H  A D  A D—H  AN2—H2  O1 0.86 2.12 2.771 (2) 133N4—H4  O1i 0.86 2.11 2.922 (2) 158Symmetry code: (i) x;y;z þ 1.Data collection: SMART (Bruker, 1998); cell refinement: SAINT(Bruker, 1998); data reduction: SAINT; program(s) used to solvestructure: SIR92 (Altomare et al., 1994); program(s) used to refinestructure: SHELXL97 (Sheldrick, 2008); molecular graphics:ORTEP-3 for Windows (Farrugia, 2012) and CAMERON (Watkin etal., 1993); software used to prepare material for publication: PARST(Nardelli, 1995) and PLATON (Spek, 2009).AcknowledgementsUSIC, Karnatak University, Dharwad, is greatly acknowl-edged for the single-crystal XRD data collection. BMH isgrateful to the UGC for financial support in the form of anRFSMS scholarship.Supporting information for this paper is available from the IUCrelectronic archives (Reference: LH5732).ReferencesAli, M. A., Mirza, A. H., Bakar, H. J. H. A. & Bernhardt, P. V. (2011).Polyhedron, 30, 556–564.Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C.,Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.Bharti, S. K., Nath, G., Tilak, R. & Singh, S. K. (2010). Eur. J. Med. Chem. 45,651–660.Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin,USA.Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.Kondratieva, M. L., Pepeleva, A. V., Belskaia, N. P., Koksharov, A. V.,Groundwater, P. V., Robeyns, K., Van Meervelt, L., Dehaen, W., Fan, Z. J. &Bakulev, V. A. (2007). Tetrahedron, 63, 3042–3048.Nardelli, M. (1995). J. Appl. Cryst. 28, 659.Sadık, G., Necmi, D., Ibrahim, Y., Alaaddin, C¸. & Dinc¸er, M. (2004). ActaCryst. E60, o889–o891.Sheldrick, G. M. (1996). SADABS. University of Go¨ttingen, Germany.data reportsActa Cryst. (2014). E70, o1177–o1178 doi:10.1107/S1600536814022715 Halasangi et al. o1177ISSN 1600-5368Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.Spek, A. L. (2009). Acta Cryst. D65, 148–155.Watkin, D. M., Pearce, L. & Prout, C. K. (1993). CAMERON. ChemicalCrystallography Laboratory, University of Oxford, England.data reportso1178 Halasangi et al.  C17H12N4OS Acta Cryst. (2014). E70, o1177–o1178supporting informationsup-1Acta Cryst. (2014). E70, o1177–o1178    supporting informationActa Cryst. (2014). E70, o1177–o1178    [doi:10.1107/S1600536814022715]Crystal structure of 3-[(E)-2-(4-phenyl-1,3-thiazol-2-yl)hydrazin-1-yl-idene]indolin-2-oneBhimashankar M. Halasangi, Prema S. Badami, Sangamesh A. Patil and G. N. Anil KumarS1. Experimental S1.1. Synthesis and crystallization An ethanolic solution of 1.81g (0.01 M) of 2-hydrazino-4-phenylthiazole was added drop wise to an etanolic solution of 1.47g (0.01 M) of isatin with constant stirring. After the complete addition, the reaction mixture was stirred further for 8-9 hrs until the solid separated out from the reaction mixture. The separated solid was filtered and washed with cold alcohol, dried and recrystallized from DMF (Yield: 95 %. MP: 443-446K). Block-shaped colourless crystals were obtained by slow evaporation of a solution of the title compound at room temperature in DMF:water in the ratio 2:1. S1.2. Refinement H atoms were placed in idealized positions and refined using a riding-model approximation with N—H = 0.86 Å, C—H = 0.93 Å and with Uiso(H) = 1.2Ueq(N,C). S2. Comment Isatin derivatives and compounds containing a thiazole ring are class of organic compounds which have fascinated many synthetic researchers due to their wide range of biological activity ( Ali et al., 2011; Bharti et al., 2010; Kondratieva et al., 2007).The molecular structure of the title compound is shown in Fig. 1. An intramolecular N—H···O hydrogen bond is observed. The thiazole ring is essentially planar with a maximum deviation of 0.005 (2) Å for atom N1. The thiazole ring (S1/C9/N1/C7/C8) forms dihedral angles of 10.8 (2)° with the phenyl ring (C1–C6) and 3.1 (3)° with the indole ring system (C10—C16/N4/C17, with a maximum deviation of 0.035 (2)Å for atom C17). The dihedral angle between the phenyl ring and the indole ring system is 11.5 (1)Å. In the crystal, pairs of N—H···O hydrogen bonds form inversion dimers (Fig. 2). A closely related structure appears in the literature (Sadik, et al., 2004). supporting informationsup-2Acta Cryst. (2014). E70, o1177–o1178    Figure 1The molecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level. The dashed line indicates an intramolecular N—H···N bond Figure 2Part of the crystal structure with hydrogen bonds indicated as dotted lines 3-[(E)-2-(4-Phenyl-1,3-thiazol-2-yl)hydrazin-1-ylidene]indolin-2-one Crystal data C17H12N4OSMr = 320.37Monoclinic, P21/cHall symbol: -P 2ybca = 17.7108 (8) Åb = 5.1411 (2) Åc = 15.9065 (6) Åβ = 94.706 (3)°V = 1443.45 (10) Å3Z = 4supporting informationsup-3Acta Cryst. (2014). E70, o1177–o1178    F(000) = 664Dx = 1.474 Mg m−3Mo Kα radiation, λ = 0.71073 Åµ = 0.23 mm−1T = 296 KBlock, colourless0.35 × 0.31 × 0.25 mmData collection Bruker SMART CCD area-detector diffractometerGraphite monochromatorφ and ω scansAbsorption correction: multi-scan (SADABS; Sheldrick, 1996)Tmin = 0.887, Tmax = 0.93411530 measured reflections3142 independent reflections2124 reflections with I > 2σ(I)Rint = 0.039θmax = 27.1°, θmin = 2.3°h = −22→22k = −6→6l = −20→20Refinement Refinement on F2Least-squares matrix: fullR[F2 > 2σ(F2)] = 0.046wR(F2) = 0.109S = 1.093142 reflections208 parameters0 restraintsPrimary atom site location: structure-invariant direct methodsSecondary atom site location: difference Fourier mapHydrogen site location: inferred from neighbouring sitesH-atom parameters constrainedw = 1/[σ2(Fo2) + (0.0451P)2 + 0.0098P] where P = (Fo2 + 2Fc2)/3(Δ/σ)max < 0.001Δρmax = 0.20 e Å−3Δρmin = −0.25 e Å−3Special details 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.Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) x y z Uiso*/UeqS1 0.33816 (3) 0.66660 (12) 0.39879 (3) 0.04097 (19)O1 0.08908 (8) 0.2212 (3) 0.51706 (8) 0.0481 (4)N1 0.28727 (8) 0.7985 (3) 0.54037 (9) 0.0325 (4)N2 0.21944 (9) 0.4599 (3) 0.46996 (9) 0.0369 (4)H2 0.1873 0.4489 0.5075 0.044*N3 0.21516 (9) 0.3013 (3) 0.40283 (9) 0.0341 (4)N4 0.05982 (9) −0.1170 (3) 0.42364 (9) 0.0387 (5)H4 0.0225 −0.1842 0.4474 0.046*C1 0.43038 (11) 1.3281 (4) 0.58140 (12) 0.0359 (5)H1 0.4504 1.335 0.5292 0.043*C2 0.45583 (11) 1.5006 (4) 0.64372 (12) 0.0419 (5)H2A 0.4931 1.6214 0.6335 0.05*C3 0.42631 (12) 1.4945 (4) 0.72089 (12) 0.0410 (5)supporting informationsup-4Acta Cryst. (2014). E70, o1177–o1178    H3 0.4433 1.6113 0.7629 0.049*C4 0.37150 (12) 1.3150 (4) 0.73568 (12) 0.0415 (5)H4A 0.3512 1.3113 0.7877 0.05*C5 0.34649 (11) 1.1406 (4) 0.67384 (12) 0.0376 (5)H5 0.3098 1.0188 0.6849 0.045*C6 0.37525 (10) 1.1438 (4) 0.59528 (11) 0.0304 (5)C7 0.34960 (10) 0.9552 (4) 0.52935 (11) 0.0309 (5)C8 0.38282 (11) 0.9102 (4) 0.45680 (11) 0.0367 (5)H8 0.4247 1.0007 0.4406 0.044*C9 0.27677 (11) 0.6406 (4) 0.47676 (11) 0.0314 (5)C10 0.16106 (11) 0.1315 (4) 0.39588 (11) 0.0319 (5)C11 0.14763 (10) −0.0560 (4) 0.32827 (11) 0.0317 (5)C12 0.18154 (11) −0.1039 (4) 0.25430 (12) 0.0409 (5)H12 0.222 −0.003 0.2397 0.049*C13 0.15406 (12) −0.3045 (4) 0.20274 (12) 0.0451 (6)H13 0.1762 −0.3386 0.1528 0.054*C14 0.09393 (12) −0.4556 (4) 0.22454 (12) 0.0422 (6)H14 0.0768 −0.5912 0.1893 0.051*C15 0.05887 (11) −0.4091 (4) 0.29754 (12) 0.0392 (5)H15 0.0183 −0.51 0.312 0.047*C16 0.08638 (10) −0.2078 (4) 0.34775 (11) 0.0319 (5)C17 0.10069 (11) 0.0896 (4) 0.45404 (12) 0.0362 (5)Atomic displacement parameters (Å2) U11 U22 U33 U12 U13 U23S1 0.0424 (3) 0.0466 (4) 0.0351 (3) −0.0080 (3) 0.0099 (2) −0.0052 (2)O1 0.0479 (9) 0.0568 (11) 0.0417 (8) −0.0142 (8) 0.0156 (7) −0.0154 (8)N1 0.0296 (9) 0.0333 (11) 0.0350 (8) −0.0022 (8) 0.0050 (7) −0.0018 (8)N2 0.0329 (10) 0.0424 (12) 0.0363 (9) −0.0091 (9) 0.0080 (7) −0.0058 (8)N3 0.0328 (9) 0.0359 (11) 0.0335 (8) −0.0026 (9) 0.0026 (7) −0.0024 (8)N4 0.0354 (10) 0.0422 (12) 0.0400 (9) −0.0129 (9) 0.0112 (7) −0.0035 (8)C1 0.0343 (11) 0.0375 (14) 0.0362 (10) −0.0027 (10) 0.0056 (8) 0.0039 (10)C2 0.0377 (12) 0.0398 (15) 0.0478 (12) −0.0074 (11) 0.0010 (9) −0.0001 (11)C3 0.0436 (13) 0.0342 (14) 0.0442 (12) −0.0026 (11) −0.0030 (9) −0.0071 (10)C4 0.0454 (13) 0.0432 (15) 0.0366 (11) −0.0002 (12) 0.0078 (9) −0.0046 (10)C5 0.0359 (12) 0.0366 (14) 0.0411 (11) −0.0069 (11) 0.0085 (9) −0.0020 (10)C6 0.0291 (11) 0.0275 (12) 0.0343 (10) 0.0043 (10) 0.0010 (8) 0.0020 (9)C7 0.0289 (10) 0.0285 (12) 0.0354 (10) −0.0006 (10) 0.0026 (8) 0.0023 (9)C8 0.0345 (11) 0.0377 (14) 0.0385 (11) −0.0086 (10) 0.0071 (9) −0.0001 (10)C9 0.0290 (11) 0.0309 (13) 0.0344 (10) −0.0004 (10) 0.0026 (8) 0.0012 (9)C10 0.0282 (11) 0.0341 (13) 0.0334 (10) −0.0010 (10) 0.0025 (8) 0.0010 (9)C11 0.0275 (10) 0.0331 (13) 0.0342 (10) 0.0012 (10) 0.0016 (8) −0.0001 (9)C12 0.0326 (12) 0.0505 (15) 0.0404 (11) −0.0049 (11) 0.0080 (9) −0.0022 (11)C13 0.0370 (12) 0.0588 (17) 0.0398 (11) 0.0042 (12) 0.0047 (9) −0.0104 (11)C14 0.0381 (12) 0.0428 (15) 0.0445 (12) 0.0027 (11) −0.0042 (9) −0.0094 (11)C15 0.0343 (12) 0.0387 (14) 0.0442 (11) −0.0016 (11) 0.0013 (9) −0.0029 (10)C16 0.0279 (11) 0.0358 (13) 0.0321 (10) 0.0026 (10) 0.0026 (8) −0.0003 (9)supporting informationsup-5Acta Cryst. (2014). E70, o1177–o1178    C17 0.0322 (11) 0.0398 (14) 0.0368 (11) −0.0016 (11) 0.0040 (9) −0.0008 (10)Geometric parameters (Å, º) S1—C8 1.711 (2) C4—C5 1.377 (3)S1—C9 1.7203 (19) C4—H4A 0.93O1—C17 1.240 (2) C5—C6 1.388 (2)N1—C9 1.299 (2) C5—H5 0.93N1—C7 1.389 (2) C6—C7 1.472 (3)N2—N3 1.341 (2) C7—C8 1.358 (2)N2—C9 1.374 (2) C8—H8 0.93N2—H2 0.86 C10—C11 1.449 (3)N3—C10 1.294 (2) C10—C17 1.486 (3)N4—C17 1.352 (2) C11—C12 1.386 (2)N4—C16 1.411 (2) C11—C16 1.392 (3)N4—H4 0.86 C12—C13 1.381 (3)C1—C2 1.378 (3) C12—H12 0.93C1—C6 1.391 (3) C13—C14 1.385 (3)C1—H1 0.93 C13—H13 0.93C2—C3 1.373 (3) C14—C15 1.382 (3)C2—H2A 0.93 C14—H14 0.93C3—C4 1.373 (3) C15—C16 1.372 (3)C3—H3 0.93 C15—H15 0.93C8—S1—C9 87.69 (9) C7—C8—S1 111.71 (15)C9—N1—C7 109.19 (15) C7—C8—H8 124.1N3—N2—C9 117.83 (15) S1—C8—H8 124.1N3—N2—H2 121.1 N1—C9—N2 122.80 (17)C9—N2—H2 121.1 N1—C9—S1 117.03 (15)C10—N3—N2 118.11 (16) N2—C9—S1 120.17 (14)C17—N4—C16 111.08 (16) N3—C10—C11 125.96 (17)C17—N4—H4 124.5 N3—C10—C17 127.60 (18)C16—N4—H4 124.5 C11—C10—C17 106.44 (17)C2—C1—C6 121.10 (18) C12—C11—C16 119.27 (18)C2—C1—H1 119.5 C12—C11—C10 133.79 (19)C6—C1—H1 119.5 C16—C11—C10 106.93 (16)C3—C2—C1 120.2 (2) C13—C12—C11 118.73 (19)C3—C2—H2A 119.9 C13—C12—H12 120.6C1—C2—H2A 119.9 C11—C12—H12 120.6C2—C3—C4 119.63 (19) C12—C13—C14 120.71 (19)C2—C3—H3 120.2 C12—C13—H13 119.6C4—C3—H3 120.2 C14—C13—H13 119.6C3—C4—C5 120.37 (19) C15—C14—C13 121.4 (2)C3—C4—H4A 119.8 C15—C14—H14 119.3C5—C4—H4A 119.8 C13—C14—H14 119.3C4—C5—C6 121.01 (19) C16—C15—C14 117.20 (19)C4—C5—H5 119.5 C16—C15—H15 121.4C6—C5—H5 119.5 C14—C15—H15 121.4supporting informationsup-6Acta Cryst. (2014). E70, o1177–o1178    C5—C6—C1 117.73 (18) C15—C16—C11 122.65 (18)C5—C6—C7 121.26 (18) C15—C16—N4 128.34 (18)C1—C6—C7 121.00 (17) C11—C16—N4 109.01 (17)C8—C7—N1 114.38 (17) O1—C17—N4 126.73 (19)C8—C7—C6 126.00 (18) O1—C17—C10 126.84 (19)N1—C7—C6 119.59 (16) N4—C17—C10 106.42 (17)C9—N2—N3—C10 −179.69 (17) N2—N3—C10—C17 0.7 (3)C6—C1—C2—C3 −0.6 (3) N3—C10—C11—C12 −3.6 (4)C1—C2—C3—C4 0.2 (3) C17—C10—C11—C12 176.1 (2)C2—C3—C4—C5 0.4 (3) N3—C10—C11—C16 177.11 (18)C3—C4—C5—C6 −0.7 (3) C17—C10—C11—C16 −3.2 (2)C4—C5—C6—C1 0.3 (3) C16—C11—C12—C13 −1.0 (3)C4—C5—C6—C7 179.04 (18) C10—C11—C12—C13 179.7 (2)C2—C1—C6—C5 0.3 (3) C11—C12—C13—C14 −0.2 (3)C2—C1—C6—C7 −178.37 (17) C12—C13—C14—C15 0.9 (3)C9—N1—C7—C8 0.9 (2) C13—C14—C15—C16 −0.3 (3)C9—N1—C7—C6 −177.30 (17) C14—C15—C16—C11 −0.9 (3)C5—C6—C7—C8 −167.50 (19) C14—C15—C16—N4 178.32 (18)C1—C6—C7—C8 11.2 (3) C12—C11—C16—C15 1.6 (3)C5—C6—C7—N1 10.4 (3) C10—C11—C16—C15 −178.92 (17)C1—C6—C7—N1 −170.89 (17) C12—C11—C16—N4 −177.75 (17)N1—C7—C8—S1 −0.5 (2) C10—C11—C16—N4 1.7 (2)C6—C7—C8—S1 177.49 (15) C17—N4—C16—C15 −178.68 (18)C9—S1—C8—C7 0.06 (16) C17—N4—C16—C11 0.7 (2)C7—N1—C9—N2 179.57 (17) C16—N4—C17—O1 176.05 (19)C7—N1—C9—S1 −0.8 (2) C16—N4—C17—C10 −2.7 (2)N3—N2—C9—N1 −178.05 (17) N3—C10—C17—O1 4.6 (3)N3—N2—C9—S1 2.4 (2) C11—C10—C17—O1 −175.10 (19)C8—S1—C9—N1 0.48 (16) N3—C10—C17—N4 −176.72 (18)C8—S1—C9—N2 −179.92 (16) C11—C10—C17—N4 3.6 (2)N2—N3—C10—C11 −179.72 (16)Hydrogen-bond geometry (Å, º) D—H···A D—H H···A D···A D—H···AN2—H2···O1 0.86 2.12 2.771 (2) 133N4—H4···O1i 0.86 2.11 2.922 (2) 158Symmetry code: (i) −x, −y, −z+1.

Acta Crystallographica Section E Structure Reports Online

Crystal structure of 3-[(<i>E</i>)-2-(4-phenyl-1,3-thiazol-2-yl)hydrazin-1-ylidene]indolin-2-one

http://journals.iucr.org/e/issues/2014/11/00/lh5732/lh5732.pdf

Crystal structure of 3-[(
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Crystal structure of 3-[( E

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