A. SubbiahPandi

Farrugia

G. Vimala

Ishikawa

J. Govindaraj

J. Haribabu

Kelly

Khan

R. Karvembu

Sheldrick

Spek

Acta Crystallographica Section E

In the title compound, C12H11N3O2S, the dihedral angle between the 4H-chromen-4-one ring system and the –CH=N—NH—CS—NH– unit is 6.22 (1)°. In the crystal, inversion dimers linked by pairs of N—H...O hydrogen bonds generateR22(14) loops. The dimers are reinforced by a pair of C—H...O interactions, which generateR22(10) loops.</jats:p

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Crystal structure of (2E)-N-methyl-2-[(4-oxo-4H-chromen-3-yl)methylidene]-hydrazinecarbothioamideG. Vimala,a J. Govindaraj,b J. Haribabu,c R. Karvembudand A. SubbiahPandia*aDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India,bDepartment of Physics, Pachaiyappa’s College for Men, Kancheepuram 631 501,India, cDepartment of Chemistry, National Institute of Technology, Trichy 620 015,India, and dDeparment of Chemistry, National Institute of Technology, Trichy620 015, India. *Correspondence e-mail: aspandian59@gmail.comReceived 20 September 2014; accepted 1 October 2014Edited by W. T. A. Harrison, University of Aberdeen, ScotlandIn the title compound, C12H11N3O2S, the dihedral anglebetween the 4H-chromen-4-one ring system and the–CH N—NH—CS—NH– unit is 6.22 (1). In the crystal,inversion dimers linked by pairs of N—H  O hydrogen bondsgenerate R22(14) loops. The dimers are reinforced by a pair ofC—H  O interactions, which generate R22(10) loops.Keywords: crystal structure; hydrazinecarbothioamide; 4H-chromen-4-one; biological properties; hydrogen bonding.CCDC reference: 10271561. Related literatureFor the biological properties of related compounds, see: Khanet al. (2009); Tu et al. (2013); Kelly et al. (1996). For a relatedstructure, see: Ishikawa & Watanabe (2014).2. Experimental2.1. Crystal dataC12H11N3O2S Mr = 261.30Monoclinic, P21=na = 6.3702 (7) A˚b = 20.647 (2) A˚c = 9.2717 (10) A˚ = 98.365 (3)V = 1206.5 (2) A˚3Z = 4Mo K radiation = 0.27 mm1T = 293 K0.30  0.25  0.20 mm2.2. Data collectionBruker SMART APEXII CCDdiffractometerAbsorption correction: multi-scan(SADABS; Bruker, 2008)Tmin = 0.924, Tmax = 0.94817429 measured reflections3560 independent reflections2257 reflections with I > 2(I)Rint = 0.0312.3. RefinementR[F 2 > 2(F 2)] = 0.043wR(F 2) = 0.131S = 1.063560 reflections164 parametersH-atom parameters constrainedmax = 0.22 e A˚3min = 0.24 e A˚3Table 1Hydrogen-bond geometry (A˚, ).D—H  A D—H H  A D  A D—H  AN2—H2A  O2i 0.86 2.11 2.897 (2) 152C10—H10  O2i 0.93 2.44 3.219 (2) 141Symmetry code: (i) x þ 1;y;z.Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT(Bruker, 2008); data reduction: SAINT; program(s) used to solvestructure: SHELXS97 (Sheldrick, 2008); program(s) used to refinestructure: SHELXL97 (Sheldrick, 2008); molecular graphics:ORTEP-3 for Windows (Farrugia, 2012); software used to preparematerial for publication: SHELXL97 and PLATON (Spek, 2009).AcknowledgementsThe authors thank Dr Babu Varghese, SAIF, IIT, Chennai,India, for the data collection.Supporting information for this paper is available from the IUCrelectronic archives (Reference: HB7287).ReferencesBruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin,USA.Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.Ishikawa, Y. & Watanabe, K. (2014). Acta Cryst. E70, o472.Kelly, P. F., Slawin, A. M. Z. & Soriano-Rama, A. (1996). J. Chem. Soc. DaltonTrans. pp. 53–59.Khan, K. M., Ambreen, N., Hussain, S., Perveen, S. & Choudhary, M. I. (2009).Bioorg. Med. Chem. 17, 2983–2988.Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.Spek, A. L. (2009). Acta Cryst. D65, 148–155.Tu, Q. D., Li, D., Sun, Y., Han, X. Y., Yi, F., Sha, Y., Ren, Y. L., Ding, M. W.,Feng, L. L. & Wan, J. (2013). Bioorg. Med. Chem. 21, 2826–2831.data reportsActa Cryst. (2014). E70, o1151 doi:10.1107/S1600536814021667 Vimala et al. o1151ISSN 1600-5368supporting informationsup-1Acta Cryst. (2014). E70, o1151 supporting informationActa Cryst. (2014). E70, o1151 [doi:10.1107/S1600536814021667]Crystal structure of (2E)-N-methyl-2-[(4-oxo-4H-chromen-3-yl)methyl-idene]hydrazinecarbothioamideG. Vimala, J. Govindaraj, J. Haribabu, R. Karvembu and A. SubbiahPandiS1. Comment Thiosemicarbazones are of considerable interest because of their versatile chemistry and various biological activites such as antitumor, antibacterial, antiviral, antiamoebic and antimalarial (Kelly et al., 1996). Schiff bases derived from 3-formylchromones have attracted much attention due to their biological functions such as enzyme inhibition (Khan et al., 2009; Tu et al., 2013).The structure of the title compound (Figure 1) shows that the atoms of both 4H-chromen-4-one and the –CH=N—NH—CS—NH– segments are roughly planar and the largest deviations are -0.144 (2) and -0.114 (2) Å for O2 and C12 respectively. The dihedral angles between 4H-chromen-4-one and –CH=N—NH—CS—NH—C– unit and the benzene ring of 4H-chromen-4-one and –CH=N—NH—CS—NH—C– unit are 6.22 (1) and 7.12 (1)°, respectively.In the crystal, inversion dimers linked by pairs of N—H···O hydrogen bonds generate R22(14) loops. The dimers are reinforced by a pair of C—H···O interactions, which generate R22(10) loops.S2. Experimental 1.05 g (0.01 mol) of N-methylhydrazinecarbothioamide was dissolved in 20 ml of hot ethanol and to this 1.74 g of 4-oxo-4H-Chromene-3-carbaldehydein 10 ml of ethanol was added and continuously stirred for a period of 10 min with continuous stirring. The reaction mixture was refluxed for 2 h and allowed to cool whereby shining white was filtered and washed thoroughly with ethanol and then dried in vaccum. The compound was recrystallized from hot ethanol to yield colourless blocks in 92% yield.S3. Refinement All H atoms were fixed geometrically and allowed to ride on their parent C atoms, with C—H distances fixed in the range 0.93–0.97 Å with Uiso(H) = 1.5Ueq(C) for methyl H atoms and 1.2Ueq(C) for all other H atoms.supporting informationsup-2Acta Cryst. (2014). E70, o1151 Figure 1The molecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level. Figure 2The packing of the title compound with hydrogen bonds represented by dashed lines. Hydrogen atoms not involved in these bonds are omitted for clarity. supporting informationsup-3Acta Cryst. (2014). E70, o1151 (2E)-N-Methyl-2-[(4-oxo-4H-chromen-3-yl)methylidene]hydrazinecarbothioamide Crystal data C12H11N3O2SMr = 261.30Monoclinic, P21/nHall symbol: -P 2yna = 6.3702 (7) Åb = 20.647 (2) Åc = 9.2717 (10) Åβ = 98.365 (3)°V = 1206.5 (2) Å3Z = 4F(000) = 544Dx = 1.439 Mg m−3Mo Kα radiation, λ = 0.71073 Åµ = 0.27 mm−1T = 293 KBlock, colourless0.30 × 0.25 × 0.20 mmData collection Bruker SMART APEXII CCD diffractometerRadiation source: fine-focus sealed tubeGraphite monochromatorω and φ scansAbsorption correction: multi-scan (SADABS; Bruker, 2008)Tmin = 0.924, Tmax = 0.94817429 measured reflections3560 independent reflections2257 reflections with I > 2σ(I)Rint = 0.031θmax = 30.2°, θmin = 2.0°h = −8→8k = −28→28l = −12→12Refinement Refinement on F2Least-squares matrix: fullR[F2 > 2σ(F2)] = 0.043wR(F2) = 0.131S = 1.063560 reflections164 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) + (0.056P)2 + 0.3687P] where P = (Fo2 + 2Fc2)/3(Δ/σ)max < 0.001Δρmax = 0.22 e Å−3Δρmin = −0.24 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*/UeqC1 1.1216 (3) −0.01086 (8) −0.30947 (18) 0.0402 (4)C2 1.2628 (3) −0.03414 (11) −0.3973 (2) 0.0536 (5)H2 1.3795 −0.0097 −0.4138 0.064*C3 1.2268 (4) −0.09395 (12) −0.4591 (2) 0.0615 (6)H3 1.3198 −0.1102 −0.5187 0.074*supporting informationsup-4Acta Cryst. (2014). E70, o1151 C4 1.0550 (4) −0.13046 (11) −0.4344 (2) 0.0590 (6)H4 1.0321 −0.1708 −0.4784 0.071*C5 0.9167 (3) −0.10774 (9) −0.3453 (2) 0.0485 (5)H5 0.8020 −0.1329 −0.3279 0.058*C6 0.9493 (3) −0.04658 (8) −0.28081 (17) 0.0359 (4)C7 0.8095 (3) −0.02066 (8) −0.18335 (17) 0.0353 (4)C8 0.8552 (3) 0.04523 (7) −0.13502 (17) 0.0336 (3)C9 1.0264 (3) 0.07560 (8) −0.1711 (2) 0.0429 (4)H9 1.0518 0.1177 −0.1376 0.051*C10 0.7153 (3) 0.07618 (8) −0.04415 (18) 0.0373 (4)H10 0.5918 0.0552 −0.0274 0.045*C11 0.6662 (3) 0.21399 (7) 0.16614 (18) 0.0367 (4)C12 0.9249 (4) 0.30201 (10) 0.2112 (3) 0.0619 (6)H12A 0.8427 0.3380 0.1689 0.093*H12B 1.0703 0.3075 0.1976 0.093*H12C 0.9158 0.2998 0.3136 0.093*N1 0.7607 (2) 0.13156 (6) 0.01244 (15) 0.0367 (3)N2 0.6206 (2) 0.15691 (6) 0.09629 (16) 0.0400 (3)H2A 0.5048 0.1368 0.1046 0.048*N3 0.8432 (3) 0.24283 (7) 0.14142 (18) 0.0456 (4)H3A 0.9141 0.2252 0.0797 0.055*O1 1.1633 (2) 0.04988 (6) −0.25169 (15) 0.0482 (3)O2 0.6644 (2) −0.05230 (6) −0.14399 (16) 0.0550 (4)S1 0.49924 (9) 0.24309 (2) 0.27366 (6) 0.05253 (18)Atomic displacement parameters (Å2) U11 U22 U33 U12 U13 U23C1 0.0460 (10) 0.0399 (9) 0.0355 (9) 0.0073 (7) 0.0089 (7) 0.0057 (7)C2 0.0545 (12) 0.0624 (12) 0.0470 (11) 0.0127 (10) 0.0180 (9) 0.0078 (9)C3 0.0724 (15) 0.0678 (14) 0.0469 (12) 0.0299 (12) 0.0167 (10) 0.0005 (10)C4 0.0805 (16) 0.0484 (11) 0.0468 (11) 0.0189 (11) 0.0050 (11) −0.0096 (9)C5 0.0583 (12) 0.0403 (9) 0.0451 (10) 0.0052 (8) 0.0011 (9) −0.0057 (8)C6 0.0422 (9) 0.0336 (8) 0.0307 (8) 0.0050 (7) 0.0018 (7) 0.0015 (6)C7 0.0365 (9) 0.0348 (8) 0.0339 (8) −0.0016 (6) 0.0024 (7) −0.0008 (6)C8 0.0377 (9) 0.0302 (7) 0.0328 (8) −0.0005 (6) 0.0052 (7) 0.0005 (6)C9 0.0517 (11) 0.0329 (8) 0.0463 (10) −0.0033 (7) 0.0147 (8) 0.0002 (7)C10 0.0397 (9) 0.0353 (8) 0.0375 (9) −0.0028 (7) 0.0080 (7) −0.0028 (7)C11 0.0430 (10) 0.0274 (7) 0.0401 (9) 0.0026 (6) 0.0072 (7) 0.0012 (6)C12 0.0564 (13) 0.0406 (10) 0.0913 (17) −0.0104 (9) 0.0190 (12) −0.0151 (10)N1 0.0445 (8) 0.0310 (7) 0.0357 (7) 0.0011 (6) 0.0097 (6) −0.0006 (5)N2 0.0427 (8) 0.0328 (7) 0.0469 (8) −0.0036 (6) 0.0150 (7) −0.0058 (6)N3 0.0500 (9) 0.0330 (7) 0.0578 (10) −0.0036 (6) 0.0213 (8) −0.0072 (6)O1 0.0510 (8) 0.0410 (7) 0.0572 (8) −0.0043 (5) 0.0233 (6) 0.0007 (6)O2 0.0539 (8) 0.0445 (7) 0.0712 (10) −0.0181 (6) 0.0241 (7) −0.0158 (6)S1 0.0572 (3) 0.0399 (3) 0.0659 (4) 0.0015 (2) 0.0269 (3) −0.0093 (2)supporting informationsup-5Acta Cryst. (2014). E70, o1151 Geometric parameters (Å, º) C1—O1 1.374 (2) C8—C10 1.460 (2)C1—C6 1.380 (2) C9—O1 1.338 (2)C1—C2 1.384 (3) C9—H9 0.9300C2—C3 1.367 (3) C10—N1 1.274 (2)C2—H2 0.9300 C10—H10 0.9300C3—C4 1.375 (3) C11—N3 1.324 (2)C3—H3 0.9300 C11—N2 1.356 (2)C4—C5 1.375 (3) C11—S1 1.6715 (17)C4—H4 0.9300 C12—N3 1.444 (2)C5—C6 1.400 (2) C12—H12A 0.9600C5—H5 0.9300 C12—H12B 0.9600C6—C7 1.459 (2) C12—H12C 0.9600C7—O2 1.230 (2) N1—N2 1.3695 (18)C7—C8 1.449 (2) N2—H2A 0.8600C8—C9 1.342 (2) N3—H3A 0.8600O1—C1—C6 121.78 (15) O1—C9—C8 124.97 (16)O1—C1—C2 116.17 (17) O1—C9—H9 117.5C6—C1—C2 122.05 (17) C8—C9—H9 117.5C3—C2—C1 118.5 (2) N1—C10—C8 120.64 (15)C3—C2—H2 120.8 N1—C10—H10 119.7C1—C2—H2 120.8 C8—C10—H10 119.7C2—C3—C4 121.0 (2) N3—C11—N2 115.89 (15)C2—C3—H3 119.5 N3—C11—S1 124.97 (13)C4—C3—H3 119.5 N2—C11—S1 119.14 (13)C5—C4—C3 120.5 (2) N3—C12—H12A 109.5C5—C4—H4 119.7 N3—C12—H12B 109.5C3—C4—H4 119.7 H12A—C12—H12B 109.5C4—C5—C6 119.8 (2) N3—C12—H12C 109.5C4—C5—H5 120.1 H12A—C12—H12C 109.5C6—C5—H5 120.1 H12B—C12—H12C 109.5C1—C6—C5 118.20 (16) C10—N1—N2 116.71 (14)C1—C6—C7 119.82 (15) C11—N2—N1 119.45 (14)C5—C6—C7 121.97 (16) C11—N2—H2A 120.3O2—C7—C8 122.21 (15) N1—N2—H2A 120.3O2—C7—C6 122.79 (15) C11—N3—C12 124.28 (16)C8—C7—C6 115.00 (14) C11—N3—H3A 117.9C9—C8—C7 119.72 (15) C12—N3—H3A 117.9C9—C8—C10 121.73 (15) C9—O1—C1 118.35 (14)C7—C8—C10 118.52 (14)O1—C1—C2—C3 −179.09 (17) C6—C7—C8—C9 −5.2 (2)C6—C1—C2—C3 1.2 (3) O2—C7—C8—C10 −4.0 (2)C1—C2—C3—C4 −0.3 (3) C6—C7—C8—C10 176.46 (14)C2—C3—C4—C5 −0.8 (3) C7—C8—C9—O1 0.6 (3)C3—C4—C5—C6 0.9 (3) C10—C8—C9—O1 178.80 (16)supporting informationsup-6Acta Cryst. (2014). E70, o1151 O1—C1—C6—C5 179.29 (15) C9—C8—C10—N1 −5.1 (3)C2—C1—C6—C5 −1.0 (3) C7—C8—C10—N1 173.16 (15)O1—C1—C6—C7 −1.8 (2) C8—C10—N1—N2 −179.90 (14)C2—C1—C6—C7 177.85 (16) N3—C11—N2—N1 3.0 (2)C4—C5—C6—C1 −0.1 (3) S1—C11—N2—N1 −177.53 (12)C4—C5—C6—C7 −178.91 (17) C10—N1—N2—C11 176.29 (15)C1—C6—C7—O2 −173.71 (17) N2—C11—N3—C12 −176.58 (18)C5—C6—C7—O2 5.1 (3) S1—C11—N3—C12 4.0 (3)C1—C6—C7—C8 5.8 (2) C8—C9—O1—C1 3.8 (3)C5—C6—C7—C8 −175.36 (16) C6—C1—O1—C9 −3.1 (2)O2—C7—C8—C9 174.28 (17) C2—C1—O1—C9 177.22 (16)Hydrogen-bond geometry (Å, º) D—H···A D—H H···A D···A D—H···AN2—H2A···O2i 0.86 2.11 2.897 (2) 152C10—H10···O2i 0.93 2.44 3.219 (2) 141Symmetry code: (i) −x+1, −y, −z.

Acta Crystallographica Section E Structure Reports Online

Crystal structure of (2E)-N-methyl-2-[(4-oxo-4H-chromen-3-yl)methylidene]hydrazinecarbothioamide

http://journals.iucr.org/e/issues/2014/11/00/hb7287/hb7287.pdf

Crystal structure of (2
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Crystal structure of (2 E

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