The structure of the title compound, C6H4O3S, displays inter­molecular hydrogen-bonding dimers. The structure exhibits a thienyl-ring flip disorder of the main mol­ecule [occupancy ratio = 91.3 (2):8.7 (2)]

Bernstein

Crundwell

Farrugia

Guy Crundwell

Sheldrick

Spek

English

PubMed

The structure of the title compound, C6H4O3S, displays intermolecular hydrogen-bonding dimers. The structure exhibits a thienyl-ring flip disorder of the main molecule [occupancy ratio = 91.3&amp;#8197;(2):8.7&amp;#8197;(2)]

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Acta Crystallographica Section E Structure Reports Online

2-Oxo-2-(2-thienyl)acetic acid

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2-Oxo-2-(2-thienyl)acetic acidGuy CrundwellDepartment of Chemistry and Biochemistry, Central Connecticut State University,1619 Stanley Street, New Britain, CT 06053, USACorrespondence e-mail: crundwellg@ccsu.eduReceived 13 October 2010; accepted 27 October 2010Key indicators: single-crystal X-ray study; T = 293 K; mean (C–C) = 0.002 A˚;disorder in main residue; R factor = 0.037; wR factor = 0.106; data-to-parameterratio = 18.5.The structure of the title compound, C6H4O3S, displaysintermolecular hydrogen-bonding dimers. The structure exhi-bits a thienyl-ring flip disorder of the main molecule[occupancy ratio = 91.3 (2):8.7 (2)].Related literatureFor a discussion of ring-flip disorder in unsubstituted 2- and 3-thienyl rings, see: Crundwell et al. (2003). For information onsimple O—H  O interactions, see: Bernstein et al. (1995).ExperimentalCrystal dataC6H4O3SMr = 156.15Monoclinic, P21=ca = 3.7481 (10) A˚b = 15.314 (3) A˚c = 10.727 (3) A˚ = 93.30 (2)V = 614.7 (3) A˚3Z = 4Mo K radiation = 0.46 mm1T = 293 K0.34  0.21  0.11 mmData collectionOxford Diffraction XcaliburSapphire3 diffractometerAbsorption correction: multi-scan(CrysAlis PRO; OxfordDiffraction, 2009)Tmin = 0.944, Tmax = 1.0006475 measured reflections1927 independent reflections1512 reflections with I > 2(I)Rint = 0.032RefinementR[F 2 > 2(F 2)] = 0.037wR(F 2) = 0.106S = 1.091927 reflections104 parameters12 restraintsH-atom parameters constrainedmax = 0.51 e A˚3min = 0.29 e A˚3Table 1Hydrogen-bond geometry (A˚, ).D—H  A D—H H  A D  A D—H  AO1—H1  O2i 0.82 1.82 2.637 (2) 176Symmetry code: (i) x þ 1;yþ 2;zþ 1.Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cellrefinement: CrysAlis PRO; data reduction: CrysAlis PRO;program(s) used to solve structure: SHELXS97 (Sheldrick, 2008);program(s) used to refine structure: SHELXL97 (Sheldrick, 2008);molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek,2009); software used to prepare material for publication: SHELXTL(Sheldrick, 2008).This work was funded by a CSU-AAUP Faculty ResearchGrant.Supplementary data and figures for this paper are available from theIUCr electronic archives (Reference: BX2317).ReferencesBernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem.Int. Ed. Engl. 34, 1555–1573.Crundwell, G., Sullivan, J., Pelto, R. & Kantardjieff, K. (2003). J. Chem.Crystallogr. 33, 239–244.Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton,Oxfordshire, England.Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.Spek, A. L. (2009). Acta Cryst. D65, 148–155.organic compoundso3056 Guy Crundwell doi:10.1107/S160053681004403X Acta Cryst. (2010). E66, o3056Acta Crystallographica Section EStructure ReportsOnlineISSN 1600-5368supporting informationsup-1Acta Cryst. (2010). E66, o3056    supporting informationActa Cryst. (2010). E66, o3056    [https://doi.org/10.1107/S160053681004403X]2-Oxo-2-(2-thienyl)acetic acidGuy CrundwellS1. Comment The structure of 2-oxo-2-(2-thienyl)acetic acid, C6H4O3S, has monoclinic (P21/c) symmetry. The structure displays intermolecular hydrogen bonding dimers. The structure exhibits a thienyl-ring flip disorder of the main molecule.The structure of the title compound displays centrosymmetric R22(8) dimers by a simple O—H···O interactions (Bernstein et al., 1995). The structure exhibits a thienyl-ring flip disorder of the main molecule with occupancy ratios of 91.3 (2)% to 8.7 (2)%.S2. Experimental The title compound was purchased as 2-thiopheneglyoxylic acid from Aldrich (95% purity). Crystals for this x-ray diffraction study were harvested from methanol during routine recrystallization.S3. Refinement During refinement, the thienyl ring showed evidence of ring-flip disorder which is common for unsubstituted 2- and 3-thienyl rings (Crundwell et al., 2003). After finding three of the flipped disordered atoms in the difference map, the rest of the ring was generated and modeled. The final model suggested that the thienyl ring disorder was 8.7 (2)%.Hydrogen atoms on carbons were included in calculated positions with a C—H distance of 0.93 Å and were included in the refinement in riding motion approximation with Uiso = 1.2Ueq of the carrier atom.The hydroxyl hydrogen was included in a calculated position with a O—H distance of 0.82 Å and was included in the refinement in riding motion approximation with Uiso = 1.2Ueq of the carrier atom.Figure 1A view of the title compound (Farrugia, 1997). Displacement ellipsoids are drawn at the 50% probability level. supporting informationsup-2Acta Cryst. (2010). E66, o3056    2-Oxo-2-(2-thienyl)acetic acid Crystal data C6H4O3SMr = 156.15Monoclinic, P21/cHall symbol: -P 2ybca = 3.7481 (10) Åb = 15.314 (3) Åc = 10.727 (3) Åβ = 93.30 (2)°V = 614.7 (3) Å3Z = 4F(000) = 320Dx = 1.687 Mg m−3Melting point: 361 KMo Kα radiation, λ = 0.71073 ÅCell parameters from 6632 reflectionsθ = 3.8–32.0°µ = 0.46 mm−1T = 293 KPlate, yellow0.34 × 0.21 × 0.11 mmData collection Oxford Diffraction Xcalibur Sapphire3 diffractometerRadiation source: Enhance (Mo) X-ray SourceGraphite monochromatorDetector resolution: 16.1790 pixels mm-1ω scansAbsorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)Tmin = 0.944, Tmax = 1.0006475 measured reflections1927 independent reflections1512 reflections with I > 2σ(I)Rint = 0.032θmax = 32.0°, θmin = 3.8°h = −5→5k = −22→16l = −15→15Refinement Refinement on F2Least-squares matrix: fullR[F2 > 2σ(F2)] = 0.037wR(F2) = 0.106S = 1.091927 reflections104 parameters12 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) + (0.0678P)2 + 0.018P] where P = (Fo2 + 2Fc2)/3(Δ/σ)max = 0.002Δρmax = 0.51 e Å−3Δρmin = −0.29 e Å−3Special details Experimental. Hydrogen atoms on carbons were included in calculated positions with a C—H distance of 0.93 Å and were included in the refinement in riding motion approximation with Uiso = 1.2Ueq of the carrier atom.The hydroxyl hydrogen was included in a calculated position with a O—H distance of 0.82 Å and was included in the refinement in riding motion approximation with Uiso = 1.2Ueq of the carrier atom.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.supporting informationsup-3Acta Cryst. (2010). E66, o3056    Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) x y z Uiso*/Ueq Occ. (<1)O1 0.1858 (3) 0.98317 (6) 0.36658 (10) 0.0261 (3)H1 0.2759 1.0208 0.4128 0.039*O2 0.5095 (3) 0.89316 (7) 0.49326 (9) 0.0207 (2)C1 0.2916 (4) 0.90590 (8) 0.40596 (12) 0.0167 (3)C2 0.1123 (4) 0.83170 (8) 0.32857 (12) 0.0156 (3)O3 −0.0839 (3) 0.85113 (7) 0.23733 (9) 0.0207 (2)C3 0.1813 (3) 0.74199 (8) 0.36784 (12) 0.0153 (3) 0.9131 (17)C4 0.3362 (8) 0.70703 (19) 0.4767 (2) 0.0176 (4) 0.9131 (17)H4 0.4368 0.7412 0.5413 0.021* 0.9131 (17)C5 0.3282 (10) 0.61491 (14) 0.4812 (2) 0.0158 (3) 0.9131 (17)H5 0.4176 0.5815 0.5484 0.019* 0.9131 (17)C6 0.1687 (5) 0.58091 (10) 0.37166 (15) 0.0158 (3) 0.9131 (17)H6 0.1417 0.5214 0.3564 0.019* 0.9131 (17)S1 0.02766 (10) 0.65987 (2) 0.26826 (3) 0.01633 (14) 0.9131 (17)C3B 0.1813 (3) 0.74199 (8) 0.36784 (12) 0.0153 (3) 0.0869 (17)C4B 0.057 (4) 0.6842 (10) 0.2959 (14) 0.01633 (14) 0.0869 (17)H4B −0.0609 0.6947 0.2187 0.020* 0.0869 (17)C5B 0.122 (6) 0.5982 (11) 0.350 (2) 0.0158 (3) 0.0869 (17)H5B 0.0539 0.5454 0.3127 0.019* 0.0869 (17)C6B 0.303 (13) 0.6081 (13) 0.464 (3) 0.0158 (3) 0.0869 (17)H6B 0.3739 0.5612 0.5151 0.019* 0.0869 (17)S1B 0.384 (3) 0.7158 (6) 0.5057 (7) 0.0176 (4) 0.0869 (17)Atomic displacement parameters (Å2) U11 U22 U33 U12 U13 U23O1 0.0349 (6) 0.0124 (4) 0.0291 (6) 0.0006 (4) −0.0140 (4) −0.0003 (4)O2 0.0264 (5) 0.0153 (5) 0.0193 (5) 0.0004 (4) −0.0080 (4) −0.0003 (4)C1 0.0180 (6) 0.0151 (6) 0.0170 (6) −0.0003 (5) 0.0004 (5) −0.0007 (5)C2 0.0166 (6) 0.0150 (6) 0.0152 (6) 0.0009 (5) −0.0005 (4) −0.0003 (5)O3 0.0245 (5) 0.0203 (5) 0.0166 (5) 0.0016 (4) −0.0060 (4) 0.0009 (4)C3 0.0159 (6) 0.0132 (6) 0.0165 (6) 0.0006 (5) −0.0005 (5) −0.0015 (5)C4 0.0204 (11) 0.0172 (9) 0.0147 (13) −0.0002 (7) −0.0017 (9) −0.0020 (9)C5 0.0181 (9) 0.0144 (7) 0.0147 (10) 0.0001 (6) −0.0009 (7) −0.0009 (6)C6 0.0160 (8) 0.0128 (7) 0.0184 (8) 0.0012 (6) −0.0017 (6) 0.0023 (6)S1 0.0178 (2) 0.0142 (2) 0.0167 (2) −0.00080 (14) −0.00148 (14) −0.00162 (13)C3B 0.0159 (6) 0.0132 (6) 0.0165 (6) 0.0006 (5) −0.0005 (5) −0.0015 (5)C4B 0.0178 (2) 0.0142 (2) 0.0167 (2) −0.00080 (14) −0.00148 (14) −0.00162 (13)C5B 0.0160 (8) 0.0128 (7) 0.0184 (8) 0.0012 (6) −0.0017 (6) 0.0023 (6)C6B 0.0181 (9) 0.0144 (7) 0.0147 (10) 0.0001 (6) −0.0009 (7) −0.0009 (6)S1B 0.0204 (11) 0.0172 (9) 0.0147 (13) −0.0002 (7) −0.0017 (9) −0.0020 (9)supporting informationsup-4Acta Cryst. (2010). E66, o3056    Geometric parameters (Å, º) O1—C1 1.3102 (16) C5—C6 1.389 (2)O1—H1 0.8200 C5—H5 0.9300O2—C1 1.2223 (16) C6—S1 1.7041 (15)C1—C2 1.5387 (19) C6—H6 0.9300C2—O3 1.2265 (17) C4B—C5B 1.452 (16)C2—C3 1.4558 (18) C4B—H4B 0.9300C3—C4 1.382 (3) C5B—C6B 1.380 (17)C3—S1 1.7272 (13) C5B—H5B 0.9300C4—C5 1.412 (3) C6B—S1B 1.730 (18)C4—H4 0.9300 C6B—H6B 0.9300C1—O1—H1 109.5 C6—C5—H5 124.6O2—C1—O1 124.58 (12) C4—C5—H5 124.6O2—C1—C2 123.18 (12) C5—C6—S1 112.77 (15)O1—C1—C2 112.23 (11) C5—C6—H6 123.6O3—C2—C3 123.25 (12) S1—C6—H6 123.6O3—C2—C1 118.33 (12) C6—S1—C3 91.96 (7)C3—C2—C1 118.42 (11) C5B—C4B—H4B 124.7C4—C3—C2 132.00 (15) C6B—C5B—C4B 108.5 (16)C4—C3—S1 110.46 (14) C6B—C5B—H5B 125.8C2—C3—S1 117.44 (10) C4B—C5B—H5B 125.8C3—C4—C5 114.04 (18) C5B—C6B—S1B 113.7 (16)C3—C4—H4 123.0 C5B—C6B—H6B 123.1C5—C4—H4 123.0 S1B—C6B—H6B 123.1C6—C5—C4 110.76 (18)Hydrogen-bond geometry (Å, º) D—H···A D—H H···A D···A D—H···AO1—H1···O2i 0.82 1.82 2.637 (2) 176Symmetry code: (i) −x+1, −y+2, −z+1.

Acta Cryst. D65, 148–155. organic compounds o3056 Guy Crundwell doi:10.1107/S160053681004403X Acta Cryst.

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

The hydroxyl hydrogen was included in a calculated position with a O—H distance of 0.82 Å and was included in the refinement in riding motion approximation with Uiso = 1.2Ueq of the carrier atom. Figures Fig. 1. A view of the title compound (Farrugia,

The structure of the title compound displays centrosymmetric R2 2(8) dimers by a simple O—H···O interactions (Bernstein et al.,

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2-Oxo-2-(2-thien­yl)acetic acid

2-Oxo-2-(2-thienyl)acetic acid

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2-Oxo-2-(2-thien­yl)acetic acid

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2-Oxo-2-(2-thienyl)acetic acid