In the title compound, C15H14O2, the terminal rings form a dihedral angle of 52.39(4)°. The mean plane of the central ester group [r.m.s. deviation = 0.0488Å] is twisted away from the benzene and phenyl rings by 60.10(4) and 8.67(9)°, respectively. In the crystal, molecules are linked by weak C - HO hydrogen bonds, forming C(6) chains which run along [100]

Kennedy, A.R.

Moreno-Fuquen, R.

Rendón, M.

Acta Crystallographica Section E

English

PubMed

University of Strathclyde Institutional Repository

Strathprints Institutional RepositoryMoreno-Fuquen, R. and Rendón, M. and Kennedy, A.R. (2014) 3,4-dimethylphenyl benzoate. ActaCrystallographica Section E: Structure Reports, 70 (2). o194. ISSN 1600-5368Strathprints is designed to allow users to access the research output of the University of Strathclyde.Copyright c© and Moral Rights for the papers on this site are retained by the individual authorsand/or other copyright owners. You may not engage in further distribution of the material for anyprofitmaking activities or any commercial gain. You may freely distribute both the url (http://strathprints.strath.ac.uk/) and the content of this paper for research or study, educational, ornot-for-profit purposes without prior permission or charge.Any correspondence concerning this service should be sent to Strathprints administrator:mailto:strathprints@strath.ac.ukhttp://strathprints.strath.ac.uk/3,4-Dimethylphenyl benzoateRodolfo Moreno-Fuquen,a* Mauricio Rendo´na and Alan R.KennedybaDepartamento de Quı´mica - Facultad de Ciencias, Universidad del Valle, Apartado25360, Santiago de Cali, Colombia, and bWestCHEM, Department of Pure andApplied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow G1 1XL,ScotlandCorrespondence e-mail: rodimo26@yahoo.esReceived 16 January 2014; accepted 17 January 2014Key indicators: single-crystal X-ray study; T = 123 K; mean (C–C) = 0.002 A˚;R factor = 0.048; wR factor = 0.112; data-to-parameter ratio = 19.0.In the title compound, C15H14O2, the terminal rings form adihedral angle of 52.39 (4). The mean plane of the centralester group [r.m.s. deviation = 0.0488 A˚] is twisted away fromthe benzene and phenyl rings by 60.10 (4) and 8.67 (9),respectively. In the crystal, molecules are linked by weak C—H  O hydrogen bonds, forming C(6) chains which run along[100].Related literatureFor similar structures, see: Gowda et al. (2008a,b). Forhydrogen-bonding information, see: Nardelli (1995) and forhydrogen-bond motifs, see: Etter et al. (1990).ExperimentalCrystal dataC15H14O2Mr = 226.26Triclinic, P1a = 6.0293 (4) A˚b = 7.8506 (3) A˚c = 13.1163 (9) A˚ = 88.592 (4) = 77.020 (5) = 77.680 (4)V = 590.87 (6) A˚3Z = 2Mo K radiation = 0.08 mm1T = 123 K0.33  0.25  0.06 mmData collectionOxford Diffraction Xcalibur EdiffractometerAbsorption correction: multi-scan(CrysAlis PRO; Oxford Diffrac-tion, 2010)Tmin = 0.977, Tmax = 1.0005782 measured reflections2965 independent reflections2196 reflections with I > 2(I)Rint = 0.021RefinementR[F 2 > 2(F 2)] = 0.048wR(F 2) = 0.112S = 1.042965 reflections156 parametersH-atom parameters constrainedmax = 0.28 e A˚3min = 0.24 e A˚3Table 1Hydrogen-bond geometry (A˚, ).D—H  A D—H H  A D  A D—H  AC2—H2  O8i 0.95 2.47 3.3710 (18) 157Symmetry code: (i) x 1; y; z.Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cellrefinement: CrysAlis PRO; data reduction: CrysAlis PRO;program(s) used to solve structure: SHELXS97 (Sheldrick, 2008);program(s) used to refine structure: SHELX97 (Sheldrick, 2008);molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) andMercury (Macrae et al., 2006); software used to prepare material forpublication: WinGX (Farrugia, 2012).RMF thanks the Universidad del Valle, Colombia, forpartial financial support.Supporting information for this paper is available from the IUCrelectronic archives (Reference: TK5288).ReferencesEtter, M. (1990). Acc. Chem. Res. 23, 120–126.Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.Gowda, B. T., Foro, S., Babitha, K. S. & Fuess, H. (2008a). Acta Cryst. E64,o844.Gowda, B. T., Tokarcˇı´k, M., Kozˇı´sˇek, J., Babitha, K. S. & Fuess, H. (2008b).Acta Cryst. E64, o1280.Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor,R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457.Nardelli, M. (1995). J. Appl. Cryst. 28, 659.Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton,England.Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.organic compoundso194 Moreno-Fuquen et al. doi:10.1107/S1600536814001299 Acta Cryst. (2014). E70, o194Acta Crystallographica Section EStructure ReportsOnlineISSN 1600-5368supplementary materialssup-1Acta Cryst. (2014). E70, o194    supplementary materialsActa Cryst. (2014). E70, o194    [doi:10.1107/S1600536814001299]3,4-Dimethylphenyl benzoateRodolfo Moreno-Fuquen, Mauricio Rendón and Alan R. Kennedy1. Introduction 2. Experimental 2.1. Synthesis and crystallization The reagents and solvents for the synthesis were obtained from Aldrich Chemical Co., and were used without additional purification. The title molecule was synthesized using equimolar quantities of 3,4-dimethylphenol and benzoyl chloride. 3,4-Dimethylphenol (0.50 g, 4.10 mmol) was added to a solution of anhydrous aluminum chloride (0.40 g, 3.00 mmol) in anhydrous dichloromethane (25 mL). The resulting solution was cooled and benzoyl chloride (0.57 g) was added slowly at 0-5°. After complete addition, the mixture was left under stirring at room temperature for 0.5 h, and then it was heated (reflux) to 50° C for 1 h. The reaction mixture was poured onto ice (100 g). The crude product was isolated by extraction with dichloromethane, and it was separated. The solution was dried over Na2SO4 and it was evaporated at room temperature. The obtained amorphous product was dissolved in methanol and the solution was left to slow evaporation. Colourless crystals of good quality were obtained with M.pt = 322 (1) K. 2.2. Refinement All H-atoms were positioned at geometrically idealized positions with C—H distance of 0.95–0.98 Å, and with Uiso(H) = 1.2–1.5Ueq of the C-atoms to which they were bonded. 3. Results and discussion In order to obtain more detailed information about the effect of substitution of the methyl groups on the structure of benzoate system, the structure determination of 3,4-dimethyl phenyl benzoate (I) has been carried out. Two very similar molecular structures, 2,3-dimethylphenyl benzoate, DMPB1 (Gowda et al., 2008a), and 2,4-dimethylphenyl benzoate, DMPB2 (Gowda et al., 2008b), were taken for comparison with the structure (I). The rings of (I), Fig. 1, form a dihedral angle of 52.39 (4)° while in DMPB1 and DMPB2 they form dihedral angles of 87.36 (6)° and 80.25 (5)°, respectively. The other bond lengths and bond angles of DMPB1 and DMPB2 are close to the title system. The central ester moiety (C1—O7—C7(O8)—C8) is twisted away from the dimethyl-substituted benzeneand phenyl rings by 60.10 (4) and 8.67 (9)°, respectively. The crystal packing shows no classical hydrogen bonds and it is stabilized by weak C—H···O intermolecular hydrogen bonds, forming C(6) chains (Etter, 1990) along [100] (see Fig. 2). The C2 atom acts as hydrogen-bond donor to O1 atom at (x-1, +y, +z) (Nardelli, 1995); see Table 1. Computing details Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELX97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows supplementary materialssup-2Acta Cryst. (2014). E70, o194    (Farrugia, 2012) and Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 2012).Figure 1Molecular conformation and atom numbering scheme for the title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as spheres of arbitrary radius. Figure 2Part of the crystal structure of (I), showing the formation of chains which running along [100]. Symmetry code: (i) x-1, +y, +z. 3,4-Dimethylphenyl benzoate Crystal data C15H14O2Mr = 226.26Triclinic, P1Hall symbol: -P 1a = 6.0293 (4) Åb = 7.8506 (3) Åc = 13.1163 (9) Åα = 88.592 (4)°β = 77.020 (5)°γ = 77.680 (4)°supplementary materialssup-3Acta Cryst. (2014). E70, o194    V = 590.87 (6) Å3Z = 2F(000) = 240Dx = 1.272 Mg m−3Melting point: 322(1) KMo Kα radiation, λ = 0.71073 ÅCell parameters from 2013 reflectionsθ = 3.1–29.6°µ = 0.08 mm−1T = 123 KPlate, colourless0.33 × 0.25 × 0.06 mmData collection Oxford Diffraction Xcalibur E diffractometerRadiation source: fine-focus sealed tubeGraphite monochromatorω scansAbsorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)Tmin = 0.977, Tmax = 1.0005782 measured reflections2965 independent reflections2196 reflections with I > 2σ(I)Rint = 0.021θmax = 29.8°, θmin = 3.1°h = −8→8k = −10→10l = −18→18Refinement Refinement on F2Least-squares matrix: fullR[F2 > 2σ(F2)] = 0.048wR(F2) = 0.112S = 1.042965 reflections156 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) + (0.0425P)2 + 0.1253P] where P = (Fo2 + 2Fc2)/3(Δ/σ)max < 0.001Δρmax = 0.28 e Å−3Δρmin = −0.24 e Å−3Special details Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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*/UeqO7 0.50750 (18) 0.19314 (11) 0.74671 (8) 0.0239 (2)O8 0.74671 (18) 0.27031 (12) 0.83880 (8) 0.0262 (3)C1 0.4447 (2) 0.36566 (16) 0.71295 (11) 0.0202 (3)C2 0.2126 (2) 0.44540 (17) 0.74124 (11) 0.0227 (3)H2 0.1032 0.3888 0.7848 0.027*C3 0.1425 (3) 0.61121 (18) 0.70426 (11) 0.0236 (3)H3 −0.0171 0.6682 0.7231 0.028*C4 0.3009 (3) 0.69544 (17) 0.64030 (11) 0.0218 (3)C5 0.5366 (2) 0.61144 (17) 0.61281 (11) 0.0213 (3)C6 0.6075 (2) 0.44503 (17) 0.64949 (11) 0.0211 (3)H6 0.7665 0.3865 0.6310 0.025*supplementary materialssup-4Acta Cryst. (2014). E70, o194    C7 0.6508 (2) 0.16320 (16) 0.81492 (10) 0.0184 (3)C8 0.6695 (2) −0.01620 (16) 0.85620 (10) 0.0182 (3)C9 0.8327 (2) −0.07177 (17) 0.91616 (11) 0.0226 (3)H9 0.9322 0.0019 0.9267 0.027*C10 0.8508 (3) −0.23504 (18) 0.96080 (12) 0.0257 (3)H10 0.9613 −0.2727 1.0025 0.031*C11 0.7073 (3) −0.34264 (17) 0.94426 (11) 0.0252 (3)H11 0.7192 −0.4542 0.9748 0.030*C12 0.5461 (3) −0.28836 (17) 0.88330 (11) 0.0241 (3)H12 0.4495 −0.3635 0.8716 0.029*C13 0.5251 (2) −0.12484 (16) 0.83937 (11) 0.0205 (3)H13 0.4135 −0.0872 0.7982 0.025*C14 0.2186 (3) 0.87556 (18) 0.60106 (13) 0.0314 (4)H14A 0.0507 0.9147 0.6291 0.047*H14B 0.2509 0.8716 0.5244 0.047*H14C 0.3010 0.9570 0.6242 0.047*C15 0.7122 (3) 0.6999 (2) 0.54453 (12) 0.0292 (3)H15A 0.8692 0.6291 0.5400 0.044*H15B 0.7010 0.8151 0.5748 0.044*H15C 0.6807 0.7130 0.4743 0.044*Atomic displacement parameters (Å2) U11 U22 U33 U12 U13 U23O7 0.0319 (6) 0.0159 (4) 0.0298 (6) −0.0087 (4) −0.0163 (5) 0.0063 (4)O8 0.0332 (6) 0.0197 (5) 0.0327 (6) −0.0133 (4) −0.0150 (5) 0.0059 (4)C1 0.0273 (8) 0.0157 (6) 0.0211 (7) −0.0066 (5) −0.0112 (6) 0.0045 (5)C2 0.0236 (7) 0.0247 (7) 0.0220 (7) −0.0100 (6) −0.0057 (6) 0.0049 (6)C3 0.0222 (7) 0.0248 (7) 0.0240 (7) −0.0035 (6) −0.0071 (6) 0.0014 (6)C4 0.0283 (8) 0.0189 (6) 0.0206 (7) −0.0050 (6) −0.0111 (6) 0.0028 (5)C5 0.0256 (8) 0.0232 (7) 0.0181 (7) −0.0097 (6) −0.0074 (6) 0.0033 (5)C6 0.0204 (7) 0.0226 (7) 0.0207 (7) −0.0041 (5) −0.0058 (6) 0.0001 (5)C7 0.0194 (7) 0.0174 (6) 0.0188 (7) −0.0051 (5) −0.0043 (5) 0.0016 (5)C8 0.0216 (7) 0.0147 (6) 0.0175 (7) −0.0042 (5) −0.0025 (5) −0.0001 (5)C9 0.0261 (8) 0.0196 (6) 0.0249 (7) −0.0067 (5) −0.0097 (6) 0.0012 (6)C10 0.0303 (8) 0.0225 (7) 0.0241 (7) −0.0013 (6) −0.0098 (6) 0.0030 (6)C11 0.0322 (8) 0.0147 (6) 0.0251 (8) −0.0034 (6) −0.0012 (6) 0.0034 (5)C12 0.0278 (8) 0.0183 (6) 0.0264 (8) −0.0094 (6) −0.0024 (6) −0.0003 (6)C13 0.0217 (7) 0.0182 (6) 0.0225 (7) −0.0053 (5) −0.0056 (6) 0.0002 (5)C14 0.0376 (9) 0.0237 (7) 0.0361 (9) −0.0062 (6) −0.0161 (7) 0.0080 (6)C15 0.0323 (9) 0.0324 (8) 0.0270 (8) −0.0145 (7) −0.0087 (7) 0.0101 (6)Geometric parameters (Å, º) O7—C7 1.3609 (16) C8—C13 1.3950 (18)O7—C1 1.4145 (15) C9—C10 1.3892 (19)O8—C7 1.2008 (16) C9—H9 0.9500C1—C2 1.3755 (19) C10—C11 1.384 (2)C1—C6 1.383 (2) C10—H10 0.9500C2—C3 1.3909 (19) C11—C12 1.386 (2)supplementary materialssup-5Acta Cryst. (2014). E70, o194    C2—H2 0.9500 C11—H11 0.9500C3—C4 1.391 (2) C12—C13 1.3867 (18)C3—H3 0.9500 C12—H12 0.9500C4—C5 1.402 (2) C13—H13 0.9500C4—C14 1.5133 (18) C14—H14A 0.9800C5—C6 1.3943 (19) C14—H14B 0.9800C5—C15 1.504 (2) C14—H14C 0.9800C6—H6 0.9500 C15—H15A 0.9800C7—C8 1.4871 (17) C15—H15B 0.9800C8—C9 1.3872 (19) C15—H15C 0.9800C7—O7—C1 117.97 (10) C8—C9—H9 120.0C2—C1—C6 122.09 (13) C10—C9—H9 120.0C2—C1—O7 116.62 (12) C11—C10—C9 119.75 (14)C6—C1—O7 121.17 (12) C11—C10—H10 120.1C1—C2—C3 118.16 (13) C9—C10—H10 120.1C1—C2—H2 120.9 C10—C11—C12 120.31 (13)C3—C2—H2 120.9 C10—C11—H11 119.8C2—C3—C4 121.48 (14) C12—C11—H11 119.8C2—C3—H3 119.3 C11—C12—C13 120.32 (13)C4—C3—H3 119.3 C11—C12—H12 119.8C3—C4—C5 119.23 (12) C13—C12—H12 119.8C3—C4—C14 120.13 (13) C12—C13—C8 119.38 (13)C5—C4—C14 120.64 (13) C12—C13—H13 120.3C6—C5—C4 119.46 (13) C8—C13—H13 120.3C6—C5—C15 120.11 (13) C4—C14—H14A 109.5C4—C5—C15 120.43 (13) C4—C14—H14B 109.5C1—C6—C5 119.57 (13) H14A—C14—H14B 109.5C1—C6—H6 120.2 C4—C14—H14C 109.5C5—C6—H6 120.2 H14A—C14—H14C 109.5O8—C7—O7 123.50 (12) H14B—C14—H14C 109.5O8—C7—C8 125.00 (13) C5—C15—H15A 109.5O7—C7—C8 111.50 (11) C5—C15—H15B 109.5C9—C8—C13 120.17 (12) H15A—C15—H15B 109.5C9—C8—C7 117.48 (12) C5—C15—H15C 109.5C13—C8—C7 122.32 (12) H15A—C15—H15C 109.5C8—C9—C10 120.06 (13) H15B—C15—H15C 109.5C7—O7—C1—C2 −115.77 (14) C1—O7—C7—O8 −8.5 (2)C7—O7—C1—C6 67.97 (17) C1—O7—C7—C8 170.72 (11)C6—C1—C2—C3 −0.1 (2) O8—C7—C8—C9 −8.7 (2)O7—C1—C2—C3 −176.31 (12) O7—C7—C8—C9 172.01 (12)C1—C2—C3—C4 0.1 (2) O8—C7—C8—C13 169.10 (14)C2—C3—C4—C5 −0.2 (2) O7—C7—C8—C13 −10.15 (18)C2—C3—C4—C14 179.75 (13) C13—C8—C9—C10 −0.8 (2)C3—C4—C5—C6 0.4 (2) C7—C8—C9—C10 177.06 (13)C14—C4—C5—C6 −179.59 (13) C8—C9—C10—C11 0.7 (2)C3—C4—C5—C15 −179.47 (13) C9—C10—C11—C12 0.1 (2)C14—C4—C5—C15 0.6 (2) C10—C11—C12—C13 −0.8 (2)supplementary materialssup-6Acta Cryst. (2014). E70, o194    C2—C1—C6—C5 0.3 (2) C11—C12—C13—C8 0.7 (2)O7—C1—C6—C5 176.31 (12) C9—C8—C13—C12 0.1 (2)C4—C5—C6—C1 −0.4 (2) C7—C8—C13—C12 −177.65 (12)C15—C5—C6—C1 179.46 (13)Hydrogen-bond geometry (Å, º) D—H···A D—H H···A D···A D—H···AC2—H2···O8i 0.95 2.47 3.3710 (18) 157Symmetry code: (i) x−1, y, z.

Acta Cryst. A64, 112–122. organic compounds o194 Moreno-Fuquen et al. doi:10.1107/S1600536814001299 Acta Cryst.

CrysAlis PRO. Oxford Diffraction Ltd,

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) xy zU iso*/Ueq O7

Tokarc ˇı ´k, M., Koz ˇı ´s

3,4-dimethylphenyl benzoate

In the title compound, C15H14O2, the terminal rings form a dihedral angle of 52.39 (4)°. The mean plane of the central ester group [r.m.s. deviation = 0.0488 Å] is twisted away from the benzene and phenyl rings by 60.10 (4) and 8.67 (9)°, respectively. In the crystal, molecules are linked by weak C—H...O hydrogen bonds, forming C(6) chains which run along [100]

Rodolfo Moreno-Fuquen

Mauricio Rendón

Alan R. Kennedy

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3,4-Dimethylphenyl benzoate

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3,4-dimethylphenyl benzoate

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