In the crystal of the title compound, C8H8ClN3S, mol­ecules are connected by N—H⋯S hydrogen bonds into strips parallel to the (112) planes and running along [10]. One of the amino H atoms is not involved in a classical hydrogen bond. In addition, there is a rather short inter­molecular Cl⋯S distance of 3.3814 (5) Å

Aamer Saeed

Abdul Rauf

Blessing

Chohan

Hamaker

Michael Bolte

Mirkhani

Mobinikhaledi

Mohammad Subhan

Shams-ul Mahmood

Sheldrick

Spek

Thangadurai

Zhang

Acta Crystallographica Section E

English

PubMed

In the crystal of the title compound, C8H8ClN3S, mol­ecules are connected by N—H[cdots, three dots, centered]S hydrogen bonds into strips parallel to the (112) planes and running along [110]. One of the amino H atoms is not involved in a classical hydrogen bond. In addition, there is a rather short inter­molecular Cl ... S distance of 3.3814 (5) Å

Saeed, Aamer

Mahmood, Shams-ul

Bolte, Michael

Rauf, Abdul

Subhan, Mohammad

Hochschulschriftenserver - Universität Frankfurt am Main

(E)-1-(4-Chlorobenzylidene)thiosemi-carbazideAamer Saeed,a* Shams-ul Mahmood,a Michael Bolte,bAbdul Raufc and Mohammad SubhandaDepartment of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan,bInstitut fu ¨r Anorganische Chemie, J. W. Goethe-Universita ¨t Frankfurt, Max-von-Laue-Strasse 7, 60438 Frankfurt/Main, Germany,cDepartment of Chemistry, IslamiaIslamia College University, Peshawar, Pakistan, anddDepartment of Chemistry,Islamia University, Bahawalpur, PakistanCorrespondence e-mail: aamersaeed@yahoo.comReceived 20 January 2011; accepted 2 February 2011Key indicators: single-crystal X-ray study; T = 173 K; mean  (C–C) = 0.002 A ˚;R factor = 0.029; wR factor = 0.079; data-to-parameter ratio = 16.6.In the crystal of the title compound, C8H8ClN3S, molecules areconnected by N—H   S hydrogen bonds into strips parallel tothe (112) planes and running along [110]. One of the amino Hatoms is not involved in a classical hydrogen bond. In addition,there is a rather short intermolecular Cl   S distance of3.3814 (5) A ˚ .Related literatureFor background to Schiff bases, see: Mobinikhaledi et al.(2010); Hamaker et al. (2010); Mirkhani et al. (2010); Than-gadurai et al. (2002). Ji & Lu (2010a,b); Lu ¨ et al. (2008). For arelated structure, see: Zhang & Li (2008). For bioactivity, see:Chohan et al. (2004).ExperimentalCrystal dataC8H8ClN3SMr = 213.68Triclinic, P1a = 5.7611 (5) A ˚b = 7.8329 (7) A ˚c = 11.2016 (10) A ˚  = 83.852 (7)   = 75.373 (7)   = 76.353 (7) V = 474.69 (7) A ˚ 3Z =2Mo K  radiation  = 0.58 mm 1T = 173 K0.38   0.35   0.27 mmData collectionStoe IPDS II two-circlediffractometerAbsorption correction: multi-scan(MULABS; Spek, 2009; Blessing,1995)Tmin = 0.811, Tmax = 0.8608657 measured reﬂections2179 independent reﬂections2054 reﬂections with I >2  (I)Rint = 0.055ReﬁnementR[F2 >2  (F2)] = 0.029wR(F2) = 0.079S = 1.102179 reﬂections131 parametersH atoms treated by a mixture ofindependent and constrainedreﬁnement max = 0.39 e A ˚  3 min =  0.27 e A ˚  3Table 1Hydrogen-bond geometry (A ˚ ,  ).D—H   AD —H H   AD    AD —H   AN2—H2   S1i 0.863 (19) 2.628 (19) 3.4288 (12) 154.7 (16)N3—H3A   S1ii 0.877 (19) 2.65 (2) 3.5119 (12) 170.1 (17)Symmetry codes: (i)  x þ 3; y þ 1; z; (ii)  x þ 4; y; z.Data collection: X-AREA (Stoe & Cie, 2001); cell reﬁnement: X-AREA; data reduction: X-AREA; program(s) used to solve structure:SHELXS97 (Sheldrick, 2008); program(s) used to reﬁne structure:SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Sheldrick,2008); software used to prepare material for publication:SHELXL97.Supplementary data and ﬁgures for this paper are available from theIUCr electronic archives (Reference: BG2386).ReferencesBlessing, R. H. (1995). Acta Cryst. A51, 33–38.Chohan, Z. H., Pervez, H., Rauf, A., Khan, K. M., Maharvi, G. M. & Supuran,C. T. (2004). J. Enzyme Inhib. Med. Chem. 19, 161–168.Hamaker, C. G., Maryashina, O. S., Daley, D. K. & Wadler, A. L. (2010). J.Chem. Crystallogr. 40, 34–39.Ji, X.-H. & Lu, J.-F. (2010a). Acta Cryst. E66, m881.Ji, X.-H. & Lu, J.-F. (2010b). Acta Cryst. E66, m883–m884.Lu ¨, X., Wong, W.-Y. & Wong, W.-K. (2008). Eur. J. Inorg. Chem. pp. 523–528.Mirkhani, V., Kia, R., Milic, D., Vartooni, A. R. & Matkovic-Calogovic, D.(2010). Transition Met. Chem. 35, 81–87.Mobinikhaledi, A., Forughifar, N. & Kalhor, M. (2010). Turk. J. Chem. 34,367–373.Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.Spek, A. L. (2009). Acta Cryst. D65, 148–155.Stoe & Cie (2001). X-AREA. Stoe & Cie, Darmstadt, Germany.Thangadurai, T. D., Gowri, M. & Natarajan, K. (2002). Synth. Reac. Inorg. Met.Org. Chem. 32, 329–343.Zhang, X. & Li, Z. (2008). Acta Cryst. E64, o1159.organic compoundsActa Cryst. (2011). E67, o649 doi:10.1107/S1600536811004120 Saeed et al. o649Acta Crystallographica Section EStructure ReportsOnlineISSN 1600-5368supplementary materialssupplementary materialssup-1Acta Cryst. (2011). E67, o649    [ doi:10.1107/S1600536811004120 ](E)-1-(4-Chlorobenzylidene)thiosemicarbazideA. Saeed, S. Mahmood, M. Bolte, A. Rauf and M. SubhanCommentSchiff bases derived from semicarbazide and aromatic aldehydes are an important class of organic compounds becauseof their applications in many fields including inorganic, biological, and analytical chemistry (Mobinikhaledi et al., 2010;Thangadurai et al., 2002). Schiff bases are known to be versatile ligands in coordination chemistry (Ji & Lu, 2010a,2010b;Hamaker et al., 2010; Mirkhani et al., 2010). Shiff bases and their complexes are also important in material science applic-ations like organic light emitting diodes (Lü et al., 2008).The title compound features an essentially planar molecule: the largest deviation of a torsion angle from 0 or 180Å is13.02 (19)° for N1—C1—C11—C12. Bond lengths and angles do not show any unusual values. In the crystal, the moleculesare connected by N—H···S hydrogen bonds into strips parallel to the (1 1 2) planes and running along [1 1 0]. One of theamino H atoms is not involved in a classical hydrogen bond. In addition there is a rather short intermolecular Cl···Si distanceof 3.3814 (5)Å (symmetry operator (i): x - 2, y, z + 1).ExperimentalSemicarbazide, 0.137 g (1 mmol) dissolved in 5 ml e thanol was added dropwise to a solution of 4-chlorobenzaldehyde,0.122 g (1.1 mmol) in 10 ml e thanol at room temperature with continuous stirring. The reaction mixture was refluxed for4 h and completion monitored by TLC. The reaction mixture was concentrated and the resulting product was separated.Colourless single crystals of the compound, suitable for X-ray crystallography, were grown by slow evaporation from a(2:1) ethyl acetate-ethanol solution. Anal.: calcd. for C8H8N3SCl: C, 44.95; H, 3.74; N, 19.66; S, 14.98%; found: C, 45.01;H, 3.61; N, 19.81; S, 14.83%.RefinementH atoms bonded to N were freely refined. H atoms bonded to C were geometrically positioned and refined using a ridingmodel with C—H = 0.95Å and U(H) set to 1.2Ueq(C).FiguresFig. 1. Molecular structure of title compound. Displacement ellipsoids are drawn at the 50%probability level.Fig. 2. Crystal packing with intermolecular hydrogen bonds indicated as dashed lines.supplementary materialssup-2(E)-1-(4-Chlorobenzylidene)thiosemicarbazideCrystal dataC8H8ClN3S Z = 2Mr = 213.68 F(000) = 220Triclinic, P1 Dx = 1.495 Mg m−3Hall symbol: -P 1 Mo Kα radiation, λ = 0.71073 Åa = 5.7611 (5) Å Cell parameters from 7492 reflectionsb = 7.8329 (7) Å θ = 3.4–27.8°c = 11.2016 (10) Å µ = 0.58 mm−1α = 83.852 (7)° T = 173 Kβ = 75.373 (7)° Block, colourlessγ = 76.353 (7)° 0.38 × 0.35 × 0.27 mmV = 474.69 (7) Å3Data collectionStoe IPDS II two-circlediffractometer2179 independent reflectionsRadiation source: fine-focus sealed tube 2054 reflections with I > 2σ(I)graphite Rint = 0.055ω scans θmax = 27.7°, θmin = 3.4°Absorption correction: multi-scan(MULABS; Spek, 2009; Blessing, 1995) h = −7→7Tmin = 0.811, Tmax = 0.860 k = −10→108657 measured reflections l = −14→14RefinementRefinement on F2 Secondary atom site location: difference Fourier mapLeast-squares matrix: fullHydrogen site location: inferred from neighbouringsitesR[F2 > 2σ(F2)] = 0.029H atoms treated by a mixture of independent andconstrained refinementwR(F2) = 0.079w = 1/[σ2(Fo2) + (0.0425P)2 + 0.1107P]where P = (Fo2 + 2Fc2)/3S = 1.10 (Δ/σ)max = 0.0012179 reflections Δρmax = 0.39 e Å−3131 parameters Δρmin = −0.27 e Å−30 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008),Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4Primary atom site location: structure-invariant directmethodsExtinction coefficient: 0.061 (7)supplementary materialssup-3Special detailsGeometry. 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 mat-rix. 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; correlationsbetween e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment ofcell 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, convention-al 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 largeas 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*/UeqCl1 0.16691 (5) 0.24404 (4) 0.64870 (3) 0.02702 (12)S1 1.79101 (5) 0.26359 (4) −0.06509 (3) 0.02625 (12)N1 1.18834 (19) 0.23473 (14) 0.18778 (10) 0.0215 (2)N2 1.35359 (19) 0.28547 (14) 0.08531 (10) 0.0220 (2)H2 1.322 (3) 0.392 (3) 0.0550 (17) 0.033 (4)*N3 1.6366 (2) 0.03361 (14) 0.11273 (11) 0.0256 (2)H3A 1.787 (3) −0.030 (3) 0.0942 (17) 0.037 (5)*H3B 1.529 (4) 0.002 (2) 0.1674 (19) 0.037 (5)*C1 0.9739 (2) 0.33723 (16) 0.20735 (11) 0.0206 (2)H1 0.9408 0.4333 0.1503 0.025*C2 1.5844 (2) 0.18669 (15) 0.05230 (11) 0.0200 (2)C11 0.7791 (2) 0.30948 (15) 0.31550 (11) 0.0194 (2)C12 0.8261 (2) 0.19449 (17) 0.41513 (12) 0.0258 (3)H12 0.9887 0.1297 0.4129 0.031*C13 0.6388 (2) 0.17389 (17) 0.51702 (12) 0.0275 (3)H13 0.6721 0.0962 0.5847 0.033*C14 0.4012 (2) 0.26838 (16) 0.51905 (11) 0.0209 (2)C15 0.3492 (2) 0.38356 (16) 0.42174 (11) 0.0221 (2)H15 0.1859 0.4470 0.4241 0.027*C16 0.5394 (2) 0.40491 (16) 0.32075 (11) 0.0216 (2)H16 0.5060 0.4855 0.2544 0.026*Atomic displacement parameters (Å2)U11 U22 U33 U12 U13 U23Cl1 0.02137 (17) 0.02970 (19) 0.02380 (18) −0.00376 (12) 0.00323 (12) 0.00098 (12)S1 0.01985 (17) 0.02394 (18) 0.02535 (18) 0.00043 (12) 0.00505 (12) 0.00406 (12)N1 0.0187 (5) 0.0228 (5) 0.0206 (5) −0.0050 (4) 0.0009 (4) −0.0024 (4)N2 0.0171 (5) 0.0214 (5) 0.0217 (5) −0.0008 (4) 0.0018 (4) 0.0005 (4)N3 0.0193 (5) 0.0236 (5) 0.0260 (5) 0.0001 (4) 0.0024 (4) 0.0035 (4)C1 0.0185 (5) 0.0218 (5) 0.0206 (5) −0.0041 (4) −0.0026 (4) −0.0023 (4)C2 0.0192 (5) 0.0212 (5) 0.0177 (5) −0.0023 (4) −0.0021 (4) −0.0023 (4)supplementary materialssup-4C11 0.0165 (5) 0.0190 (5) 0.0215 (6) −0.0035 (4) −0.0016 (4) −0.0040 (4)C12 0.0167 (5) 0.0248 (6) 0.0298 (6) 0.0024 (4) −0.0023 (5) 0.0017 (5)C13 0.0223 (6) 0.0259 (6) 0.0278 (6) 0.0011 (5) −0.0031 (5) 0.0064 (5)C14 0.0173 (5) 0.0216 (5) 0.0209 (5) −0.0031 (4) 0.0003 (4) −0.0032 (4)C15 0.0148 (5) 0.0260 (6) 0.0233 (6) −0.0005 (4) −0.0034 (4) −0.0027 (5)C16 0.0183 (5) 0.0248 (6) 0.0201 (5) −0.0016 (4) −0.0047 (4) −0.0010 (4)Geometric parameters (Å, °)Cl1—C14 1.7435 (12) C11—C16 1.3967 (16)S1—C2 1.6992 (12) C11—C12 1.3972 (18)N1—C1 1.2853 (16) C12—C13 1.3835 (18)N1—N2 1.3824 (14) C12—H12 0.9500N2—C2 1.3530 (15) C13—C14 1.3898 (17)N2—H2 0.863 (19) C13—H13 0.9500N3—C2 1.3211 (16) C14—C15 1.3851 (17)N3—H3A 0.877 (19) C15—C16 1.3886 (17)N3—H3B 0.82 (2) C15—H15 0.9500C1—C11 1.4648 (16) C16—H16 0.9500C1—H1 0.9500C1—N1—N2 114.01 (10) C13—C12—C11 120.82 (11)C2—N2—N1 120.12 (10) C13—C12—H12 119.6C2—N2—H2 119.3 (12) C11—C12—H12 119.6N1—N2—H2 118.7 (12) C12—C13—C14 119.15 (12)C2—N3—H3A 118.9 (13) C12—C13—H13 120.4C2—N3—H3B 119.0 (13) C14—C13—H13 120.4H3A—N3—H3B 122.1 (18) C15—C14—C13 121.30 (11)N1—C1—C11 121.62 (11) C15—C14—Cl1 119.81 (9)N1—C1—H1 119.2 C13—C14—Cl1 118.88 (10)C11—C1—H1 119.2 C14—C15—C16 119.00 (11)N3—C2—N2 117.92 (11) C14—C15—H15 120.5N3—C2—S1 123.29 (9) C16—C15—H15 120.5N2—C2—S1 118.78 (9) C15—C16—C11 120.85 (11)C16—C11—C12 118.86 (11) C15—C16—H16 119.6C16—C11—C1 118.86 (11) C11—C16—H16 119.6C12—C11—C1 122.26 (10)C1—N1—N2—C2 −178.33 (11) C11—C12—C13—C14 0.5 (2)N2—N1—C1—C11 −176.64 (10) C12—C13—C14—C15 −0.6 (2)N1—N2—C2—N3 6.86 (18) C12—C13—C14—Cl1 −179.11 (10)N1—N2—C2—S1 −173.83 (8) C13—C14—C15—C16 −0.29 (19)N1—C1—C11—C16 −168.81 (11) Cl1—C14—C15—C16 178.22 (9)N1—C1—C11—C12 13.02 (19) C14—C15—C16—C11 1.31 (18)C16—C11—C12—C13 0.53 (19) C12—C11—C16—C15 −1.43 (18)C1—C11—C12—C13 178.70 (12) C1—C11—C16—C15 −179.66 (11)Hydrogen-bond geometry (Å, °)D—H···A D—H H···A D···A D—H···AN2—H2···S1i 0.863 (19) 2.628 (19) 3.4288 (12) 154.7 (16)supplementary materialssup-5N3—H3A···S1ii 0.877 (19) 2.65 (2) 3.5119 (12) 170.1 (17)Symmetry codes: (i) −x+3, −y+1, −z; (ii) −x+4, −y, −z.Fig. 1supplementary materialssup-6Fig. 2

Acta Cryst. E64, o1159. organic compounds Acta Cryst.

Crystal packing with intermolecular hydrogen bonds indicated as dashed lines.supplementary materials sup-2 (E)-1-(4-Chlorobenzylidene)thiosemicarbazide Crystal data

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) x y z Uiso*/Ueq Cl1

(E)-1-(4-Chlorobenzylidene)thiosemicarbazide

Abstract

Similar works

Full text

Available Versions

Hochschulschriftenserver - Universität Frankfurt am Main

Crossref

(E)-1-(4-Chloro­benzyl­idene)thio­semi­carbazide

Abstract

Similar works

Full text

Available Versions

Hochschulschriftenserver - Universität Frankfurt am Main

Crossref

(E)-1-(4-Chlorobenzylidene)thiosemicarbazide