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Belay, Yonas H.

Kinfe, Henok H.

Muller, Alfred

English

University of Johannesburg Institutional Repository

S-Phenyl benzothioateYonas H. Belay, Henok H. Kinfe and Alfred Muller*Research Centre for Synthesis and Catalysis, Department of Chemistry, University ofJohannesburg (APK Campus), PO Box 524, Auckland Park, Johannesburg, 2006,South AfricaCorrespondence e-mail: mullera@uj.ac.zaReceived 22 August 2012; accepted 28 August 2012Key indicators: single-crystal X-ray study; T = 100 K; mean (C–C) = 0.002 A˚;R factor = 0.032; wR factor = 0.082; data-to-parameter ratio = 12.9.In the title compound, C13H10OS, the phenyl rings are inclinedto one another by 51.12 (8). There is a short C—H  Scontact in the molecule.In the crystal, molecules are linked viaC—H  O hydrogen bonds forming chains along the a axis.Molecules are also linked by C—H   and weak –interactions [centroid–centroid distance = 3.9543 (10) A˚].Related literatureThe title compound was obtained by the reaction of thio-phenolyate and benzoyl chloride in an alkaline medium. Forbackground to the title compound, see: Reddy et al. (2010);Katritzky et al. (2007). For details of the Cambridge StructuralDatabase, see: Allen (2002).ExperimentalCrystal dataC13H10OSMr = 214.27Monoclinic, P21=ca = 5.7203 (1) A˚b = 15.1315 (3) A˚c = 12.0606 (3) A˚ = 96.867 (1)V = 1036.44 (4) A˚3Z = 4Cu K radiation = 2.49 mm1T = 100 K0.25  0.12  0.12 mmData collectionBruker APEX DUO 4K-CCDdiffractometerAbsorption correction: multi-scan(SADABS; Bruker, 2008)Tmin = 0.575, Tmax = 0.7549164 measured reflections1759 independent reflections1702 reflections with I > 2(I)Rint = 0.022RefinementR[F 2 > 2(F 2)] = 0.032wR(F 2) = 0.082S = 1.041759 reflections136 parametersH-atom parameters constrainedmax = 0.35 e A˚3min = 0.26 e A˚3Table 1Hydrogen-bond geometry (A˚, ).Cg1 and Cg2 are the centroids of the C2–C7 and C8–C13 rings, respectively.D—H  A D—H H  A D  A D—H  AC7—H7  S1 0.95 2.52 2.9592 (16) 109C13—H13  O1i 0.95 2.56 3.4889 (18) 167C10—H10  Cg1ii 0.95 2.97 3.506 (2) 117C5—H5  Cg2iii 0.95 2.73 3.5915 (19) 152Symmetry codes: (i) x  1; y; z; (ii) xþ 2;yþ 1;z; (iii) xþ 2; yþ 12;zþ 12.Data collection: APEX2 (Bruker, 2011); cell refinement: SAINT(Bruker, 2008); data reduction: SAINT and XPREP (Bruker, 2008);program(s) used to solve structure: SIR97 (Altomare et al., 1999);program(s) used to refine structure: SHELXL97 (Sheldrick, 2008);molecular graphics: DIAMOND (Brandenburg & Putz, 2005); soft-ware used to prepare material for publication: WinGX (Farrugia,1999).Research funds of the University of Johannesburg and theResearch Center for Synthesis and Catalysis are gratefullyacknowledged. Mrs Z. H. Phasha is thanked for the datacollection.Supplementary data and figures for this paper are available from theIUCr electronic archives (Reference: DS2217).ReferencesAllen, F. H. (2002). Acta Cryst. B58, 380–388.Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C.,Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J.Appl. Cryst. 32, 115–119.Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn,Germany.Bruker (2008). SADABS, SAINT and XPREP. BrukerAXS Inc., Madison,Wisconsin, USA.Bruker (2011). APEX2. BrukerAXS Inc., Madison, Wisconsin, USA.Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.Katritzky, A. R., Shestopalov, A. A. & Suzuki, K. (2007). Synthesis, 11, 1806–1813.Reddy, M. V. R., Pallela, V. R., Cosenza, S. C., Mallireddigari, M. R., Patti, R.,Bonagura, M., Truongcao, M., Akula, B., Jatiani, S. S. & Reddy, E. P. (2010).Bioorg. Med. Chem. 18, Issue 6, 2317–2326.Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.organic compoundsActa Cryst. (2012). E68, o2825 doi:10.1107/S1600536812037142 Belay et al. o2825Acta Crystallographica Section EStructure ReportsOnlineISSN 1600-5368supplementary materialssup-1Acta Cryst. (2012). E68, o2825    supplementary materialsActa Cryst. (2012). E68, o2825    [doi:10.1107/S1600536812037142]S-Phenyl benzothioateYonas H. Belay, Henok H. Kinfe and Alfred MullerComment Reaction of thiophenolyate and benzyol chloride in alkaline medium was described previously by Reddy et al., 2010. We have repeated the preparation of this compound to be used as starting material in some of our research. Benzoylation of thiophenol afforded colorless crystals of the title compound (see scheme and Figure 1) suitable for single crystal X-ray analysis of which the structure is reported herein. Molecules of the title compound crystalizes in the P21/c (Z=4) space group. All bond lengths are within their normal ranges (Allen, 2002). In the crystal packing several C—H···O/S/π interactions (see table 1, Fig. 2) as well as π-π stacking are observed (centroid to centroid distance = 3.9543 (10) Å, ring slippage = 1.366 Å).Experimental A mixture of sodium hydroxide (344 mg, 8.61 mmol) and thiophenol (0.9 ml, 8.61 mmol) were dissolved in methanol (22 ml) for about 10 minutes. Benzoyl chloride (1 ml) was added to it. The reaction mixture was stirred overnight and then poured into ice-cold water. Afterwards it was filtered and dried to afford the title compound as white crystals in 63% yield.Refinement All hydrogen atoms were positioned in geometrically idealized positions with C—H = 0.95 Å and were allowed to ride on their parent atoms with Uiso(H) = 1.2Ueq. A discrepant reflection (1 3 2) was removed in the final stages of refinementComputing details Data collection: APEX2 (Bruker, 2011); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT and XPREP (Bruker, 2008); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: WinGX (Farrugia, 1999).supplementary materialssup-2Acta Cryst. (2012). E68, o2825    Figure 1A view of (1). Displacement ellipsoids are drawn at the 50% probability level. Figure 2Packing diagram of (1) showing the C—H···O/S/π interactions as well as the π-π stacking. S-Phenyl benzothioate Crystal data C13H10OSMr = 214.27Monoclinic, P21/cHall symbol: -P 2ybca = 5.7203 (1) Åb = 15.1315 (3) Åc = 12.0606 (3) Åβ = 96.867 (1)°V = 1036.44 (4) Å3Z = 4F(000) = 448Dx = 1.373 Mg m−3supplementary materialssup-3Acta Cryst. (2012). E68, o2825    Cu Kα radiation, λ = 1.54178 ÅCell parameters from 6683 reflectionsθ = 4.7–65.8°µ = 2.49 mm−1T = 100 KRectangular, colourless0.25 × 0.12 × 0.12 mmData collection Bruker APEX DUO 4K-CCD diffractometerRadiation source: Incoatec IµS microfocus X-ray sourceIncoatec Quazar Multilayer Mirror monochromatorDetector resolution: 8.4 pixels mm-1φ and ω scansAbsorption correction: multi-scan (SADABS; Bruker, 2008)Tmin = 0.575, Tmax = 0.7549164 measured reflections1759 independent reflections1702 reflections with I > 2σ(I)Rint = 0.022θmax = 66.4°, θmin = 4.7°h = −2→6k = −17→17l = −14→13Refinement Refinement on F2Least-squares matrix: fullR[F2 > 2σ(F2)] = 0.032wR(F2) = 0.082S = 1.041759 reflections136 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) + (0.0364P)2 + 0.7558P] where P = (Fo2 + 2Fc2)/3(Δ/σ)max = 0.001Δρmax = 0.35 e Å−3Δρmin = −0.26 e Å−3Special details Experimental. The intensity data was collected on a Bruker Apex DUO 4 K CCD diffractometer using an exposure time of 5 s/frame. A total of 2274 frames were collected with a frame width of 1° covering up to θ = 66.38° with 96.3% completeness accomplished.Analytical data: mp: 53–55 °C (Lit. 54–55 °C; Katritzky et al., 2007); 1H NMR (CDCl3, 400 MHz): d 8.03 (d, J = 0.8 Hz, 1H), 8.01(d, J = 1.2 Hz, 1H), 7.62–7.58 (m, 1H), 7.52–7.44 (m, 7H), 13C NMR (CDCl3, 400 MHz): d 190.1, 136.6, 135.1, 133.6, 129.5, 129.2, 128.7, 127.5, 127.3.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 0.66521 (7) 0.44609 (2) 0.09450 (3) 0.02499 (16)O1 1.05856 (19) 0.36323 (7) 0.17500 (9) 0.0242 (3)C1 0.9304 (3) 0.42516 (10) 0.18525 (12) 0.0180 (3)C2 0.9751 (3) 0.49420 (10) 0.27395 (12) 0.0174 (3)C3 1.1950 (3) 0.49605 (10) 0.33797 (13) 0.0210 (3)H3 1.3106 0.4531 0.3262 0.025*supplementary materialssup-4Acta Cryst. (2012). E68, o2825    C4 1.2443 (3) 0.56059 (11) 0.41871 (14) 0.0237 (4)H4 1.3943 0.5619 0.462 0.028*C5 1.0767 (3) 0.62332 (11) 0.43703 (13) 0.0234 (3)H5 1.1117 0.6673 0.4928 0.028*C6 0.8580 (3) 0.62174 (11) 0.37383 (13) 0.0239 (4)H6 0.7429 0.6647 0.3863 0.029*C7 0.8067 (3) 0.55781 (11) 0.29258 (13) 0.0214 (3)H7 0.6566 0.5571 0.2493 0.026*C8 0.6486 (3) 0.35922 (10) −0.00504 (12) 0.0182 (3)C9 0.8130 (3) 0.35150 (10) −0.08087 (13) 0.0211 (3)H9 0.9497 0.3877 −0.0737 0.025*C10 0.7749 (3) 0.29047 (11) −0.16688 (13) 0.0231 (4)H10 0.8871 0.2843 −0.2184 0.028*C11 0.5735 (3) 0.23835 (10) −0.17811 (13) 0.0221 (3)H11 0.5472 0.1972 −0.2378 0.027*C12 0.4107 (3) 0.24634 (10) −0.10217 (13) 0.0210 (3)H12 0.2734 0.2105 −0.1097 0.025*C13 0.4483 (3) 0.30674 (10) −0.01499 (12) 0.0192 (3)H13 0.3376 0.312 0.0374 0.023*Atomic displacement parameters (Å2) U11 U22 U33 U12 U13 U23S1 0.0287 (3) 0.0191 (2) 0.0243 (2) 0.00622 (15) −0.00893 (16) −0.00571 (15)O1 0.0236 (6) 0.0242 (6) 0.0242 (6) 0.0056 (5) 0.0007 (4) −0.0028 (5)C1 0.0190 (7) 0.0164 (7) 0.0181 (8) −0.0014 (6) 0.0004 (6) 0.0032 (6)C2 0.0203 (7) 0.0174 (8) 0.0146 (7) −0.0018 (6) 0.0027 (6) 0.0027 (6)C3 0.0211 (8) 0.0189 (8) 0.0224 (8) 0.0007 (6) 0.0002 (6) 0.0032 (6)C4 0.0235 (8) 0.0246 (8) 0.0215 (8) −0.0034 (6) −0.0043 (6) 0.0024 (6)C5 0.0298 (8) 0.0226 (8) 0.0174 (7) −0.0044 (6) 0.0015 (6) −0.0019 (6)C6 0.0245 (8) 0.0247 (8) 0.0233 (8) 0.0008 (6) 0.0055 (6) −0.0040 (7)C7 0.0188 (8) 0.0259 (9) 0.0191 (8) 0.0003 (6) 0.0010 (6) −0.0019 (6)C8 0.0223 (8) 0.0148 (7) 0.0161 (7) 0.0031 (6) −0.0030 (6) 0.0010 (6)C9 0.0203 (8) 0.0205 (8) 0.0220 (8) −0.0013 (6) 0.0006 (6) 0.0060 (6)C10 0.0248 (8) 0.0272 (9) 0.0181 (8) 0.0047 (6) 0.0054 (6) 0.0048 (6)C11 0.0285 (8) 0.0196 (8) 0.0171 (8) 0.0045 (6) −0.0021 (6) −0.0021 (6)C12 0.0195 (7) 0.0187 (8) 0.0242 (8) −0.0010 (6) −0.0005 (6) −0.0006 (6)C13 0.0202 (8) 0.0191 (8) 0.0184 (7) 0.0030 (6) 0.0024 (6) 0.0010 (6)Geometric parameters (Å, º) S1—C8 1.7751 (15) C6—H6 0.95S1—C1 1.7894 (15) C7—H7 0.95O1—C1 1.2054 (19) C8—C13 1.387 (2)C1—C2 1.495 (2) C8—C9 1.393 (2)C2—C3 1.395 (2) C9—C10 1.386 (2)C2—C7 1.399 (2) C9—H9 0.95C3—C4 1.384 (2) C10—C11 1.390 (2)C3—H3 0.95 C10—H10 0.95C4—C5 1.385 (2) C11—C12 1.387 (2)supplementary materialssup-5Acta Cryst. (2012). E68, o2825    C4—H4 0.95 C11—H11 0.95C5—C6 1.385 (2) C12—C13 1.390 (2)C5—H5 0.95 C12—H12 0.95C6—C7 1.383 (2) C13—H13 0.95C8—S1—C1 104.81 (7) C6—C7—H7 119.9O1—C1—C2 124.23 (13) C2—C7—H7 119.9O1—C1—S1 123.81 (12) C13—C8—C9 120.70 (14)C2—C1—S1 111.96 (10) C13—C8—S1 117.35 (12)C3—C2—C7 119.34 (14) C9—C8—S1 121.36 (12)C3—C2—C1 118.40 (13) C10—C9—C8 119.29 (14)C7—C2—C1 122.24 (13) C10—C9—H9 120.4C4—C3—C2 119.85 (15) C8—C9—H9 120.4C4—C3—H3 120.1 C9—C10—C11 120.34 (14)C2—C3—H3 120.1 C9—C10—H10 119.8C3—C4—C5 120.60 (15) C11—C10—H10 119.8C3—C4—H4 119.7 C12—C11—C10 120.02 (15)C5—C4—H4 119.7 C12—C11—H11 120C6—C5—C4 119.80 (15) C10—C11—H11 120C6—C5—H5 120.1 C11—C12—C13 120.09 (14)C4—C5—H5 120.1 C11—C12—H12 120C7—C6—C5 120.21 (15) C13—C12—H12 120C7—C6—H6 119.9 C8—C13—C12 119.54 (14)C5—C6—H6 119.9 C8—C13—H13 120.2C6—C7—C2 120.20 (14) C12—C13—H13 120.2C8—S1—C1—O1 −0.46 (15) C3—C2—C7—C6 −0.1 (2)C8—S1—C1—C2 178.75 (10) C1—C2—C7—C6 −178.42 (14)O1—C1—C2—C3 10.8 (2) C1—S1—C8—C13 122.78 (12)S1—C1—C2—C3 −168.42 (11) C1—S1—C8—C9 −66.00 (14)O1—C1—C2—C7 −170.86 (15) C13—C8—C9—C10 −0.1 (2)S1—C1—C2—C7 9.93 (18) S1—C8—C9—C10 −171.00 (11)C7—C2—C3—C4 −0.1 (2) C8—C9—C10—C11 0.8 (2)C1—C2—C3—C4 178.26 (14) C9—C10—C11—C12 −0.9 (2)C2—C3—C4—C5 0.3 (2) C10—C11—C12—C13 0.3 (2)C3—C4—C5—C6 −0.2 (2) C9—C8—C13—C12 −0.5 (2)C4—C5—C6—C7 0.0 (2) S1—C8—C13—C12 170.75 (11)C5—C6—C7—C2 0.2 (2) C11—C12—C13—C8 0.4 (2)Hydrogen-bond geometry (Å, º) Cg1 and Cg2 are the centroids of the C2–C7 and C8–C13 rings, respectively.D—H···A D—H H···A D···A D—H···AC7—H7···S1 0.95 2.52 2.9592 (16) 109C13—H13···O1i 0.95 2.56 3.4889 (18) 167C10—H10···Cg1ii 0.95 2.97 3.506 (2) 117C5—H5···Cg2iii 0.95 2.73 3.5915 (19) 152Symmetry codes: (i) x−1, y, z; (ii) −x+2, −y+1, −z; (iii) −x+2, y+1/2, −z+1/2.

S-Phenyl benzothioate

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S-Phenyl benzothioate

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