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Acta Crystallogr Sect E Struct Rep Online. 2010 January 1; 66(Pt 1): o39.
Published online 2009 December 4. doi:  10.1107/S1600536809051514
PMCID: PMC2980190

2-Mesitylacetic acid

Abstract

In the title compound, C11H14O2, the dihedral angle between the CCOO carboxyl unit and the benzene ring is 85.37 (7)°. In the crystal, the mol­ecules are linked into inversion dimers by pairs of O—H(...)O hydrogen bonds.

Related literature

For background to carboxylic acids as supra­molecular synthons, see: Thalladi et al. (1996 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-00o39-scheme1.jpg

Experimental

Crystal data

  • C11H14O2
  • M r = 178.22
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-00o39-efi1.jpg
  • a = 8.2312 (16) Å
  • b = 15.366 (3) Å
  • c = 7.5708 (15) Å
  • β = 92.74 (3)°
  • V = 956.4 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 113 K
  • 0.32 × 0.18 × 0.12 mm

Data collection

  • Rigaku Saturn CCD diffractometer
  • Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 [triangle]) T min = 0.974, T max = 0.990
  • 6163 measured reflections
  • 1681 independent reflections
  • 1259 reflections with I > 2σ(I)
  • R int = 0.040

Refinement

  • R[F 2 > 2σ(F 2)] = 0.035
  • wR(F 2) = 0.104
  • S = 1.03
  • 1681 reflections
  • 123 parameters
  • H-atom parameters constrained
  • Δρmax = 0.20 e Å−3
  • Δρmin = −0.18 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 [triangle]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809051514/hb5261sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809051514/hb5261Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

supplementary crystallographic information

Comment

Carboxylic acid is a supramolecular synthon, widely used to construct supramolecular array with one to three different dimensions via hydrogen bonds (Thalladi et al., 1996). Herein the structure of the title compound (I) is reported.

In the title molecule, (Fig 1), the carbonyl moiety C1/C2/O1/O2 forms an angle of 85.3797) with the benzene ring. In the crystal packing, molecules are linked into dimers by strong O—H···O H-bonding (Table 1 & Fig 2).

Experimental

The title compound was available from Hunan institute of Chemical Industry, received without further purification. Colourless blocks of (I) were obtained by evaporation from its solution of ethyl acetate/petroleum ether 1/4 (v/v).

Refinement

All H atoms were positioned geometrically and constrained to ride on their parent atoms [C—H distances are 0.93 and 0.97Å with Uiso(H) = 1.2 Ueq(C) for aromatic and CH2 H atoms, 0.82 and 0.96Å with Uiso = 1.5Ueq (O and C) for OH and CH3 H atoms].

Figures

Fig. 1.
The molecule of (I) showing displacement ellipsoids drawn at the 50% probability level.
Fig. 2.
The dimer formed via intermolecular O—H···O hydrogen bonding.

Crystal data

C11H14O2F(000) = 384
Mr = 178.22Dx = 1.238 Mg m3
Monoclinic, P21/cMelting point: 440-442 K K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 8.2312 (16) ÅCell parameters from 2789 reflections
b = 15.366 (3) Åθ = 2.5–27.9°
c = 7.5708 (15) ŵ = 0.08 mm1
β = 92.74 (3)°T = 113 K
V = 956.4 (3) Å3Block, colourless
Z = 40.32 × 0.18 × 0.12 mm

Data collection

Rigaku Saturn CCD diffractometer1681 independent reflections
Radiation source: rotating anode1259 reflections with I > 2σ(I)
confocalRint = 0.040
Detector resolution: 7.31 pixels mm-1θmax = 25.0°, θmin = 2.5°
ω and [var phi] scansh = −9→7
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)k = −18→15
Tmin = 0.974, Tmax = 0.990l = −8→8
6163 measured reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.035H-atom parameters constrained
wR(F2) = 0.104w = 1/[σ2(Fo2) + (0.0648P)2] where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
1681 reflectionsΔρmax = 0.20 e Å3
123 parametersΔρmin = −0.17 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.109 (9)

Special 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)

xyzUiso*/Ueq
O10.36719 (12)0.93504 (6)0.08273 (12)0.0294 (3)
O20.48038 (12)1.05038 (6)0.21730 (12)0.0262 (3)
H20.52441.05480.12280.039*
C10.38084 (16)0.98320 (8)0.21106 (17)0.0190 (3)
C20.29007 (17)0.97161 (8)0.37622 (17)0.0232 (4)
H2A0.25681.02840.41730.028*
H2B0.36320.94670.46690.028*
C30.14180 (16)0.91442 (8)0.35423 (16)0.0189 (3)
C40.14441 (17)0.82764 (8)0.41446 (17)0.0205 (3)
C50.00572 (17)0.77723 (8)0.38957 (18)0.0229 (4)
H50.00760.72010.43030.027*
C6−0.13609 (17)0.80882 (8)0.30596 (17)0.0231 (4)
C7−0.13687 (17)0.89545 (8)0.25041 (17)0.0235 (4)
H7−0.23130.91830.19630.028*
C8−0.00110 (17)0.94838 (8)0.27356 (16)0.0198 (3)
C9−0.00882 (18)1.04182 (8)0.21213 (18)0.0270 (4)
H9A−0.11391.05330.15660.040*
H9B0.07361.05180.12890.040*
H9C0.00901.07980.31190.040*
C100.29354 (18)0.78874 (10)0.50715 (19)0.0316 (4)
H10A0.27260.72910.53600.047*
H10B0.31980.82070.61360.047*
H10C0.38320.79160.43080.047*
C11−0.28185 (19)0.75097 (9)0.2738 (2)0.0340 (4)
H11A−0.26060.71000.18210.051*
H11B−0.37460.78580.23820.051*
H11C−0.30350.72020.38050.051*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0363 (7)0.0287 (6)0.0241 (6)−0.0128 (5)0.0107 (5)−0.0080 (4)
O20.0285 (6)0.0279 (6)0.0229 (6)−0.0113 (4)0.0080 (4)−0.0047 (4)
C10.0194 (8)0.0168 (6)0.0207 (7)0.0004 (6)−0.0010 (6)0.0015 (5)
C20.0284 (9)0.0236 (7)0.0178 (8)−0.0039 (6)0.0027 (6)−0.0005 (5)
C30.0243 (8)0.0199 (7)0.0130 (7)−0.0031 (6)0.0064 (6)−0.0029 (5)
C40.0250 (8)0.0212 (7)0.0159 (7)0.0019 (6)0.0061 (6)−0.0016 (5)
C50.0330 (9)0.0159 (6)0.0206 (7)−0.0011 (6)0.0102 (6)−0.0005 (5)
C60.0259 (9)0.0253 (7)0.0188 (7)−0.0049 (6)0.0094 (6)−0.0048 (5)
C70.0228 (8)0.0295 (8)0.0185 (8)0.0030 (6)0.0044 (6)−0.0018 (5)
C80.0270 (8)0.0190 (7)0.0141 (7)0.0001 (6)0.0073 (6)−0.0014 (5)
C90.0343 (9)0.0233 (7)0.0237 (8)0.0029 (6)0.0055 (7)0.0014 (5)
C100.0317 (9)0.0294 (8)0.0336 (9)0.0033 (6)0.0022 (7)0.0032 (6)
C110.0329 (10)0.0366 (9)0.0332 (9)−0.0109 (7)0.0080 (7)−0.0040 (6)

Geometric parameters (Å, °)

O1—C11.2222 (15)C6—C111.5037 (18)
O2—C11.3174 (15)C7—C81.3865 (18)
O2—H20.8200C7—H70.9300
C1—C21.4976 (19)C8—C91.5096 (18)
C2—C31.5067 (17)C9—H9A0.9600
C2—H2A0.9700C9—H9B0.9600
C2—H2B0.9700C9—H9C0.9600
C3—C81.4000 (18)C10—H10A0.9600
C3—C41.4089 (18)C10—H10B0.9600
C4—C51.3850 (18)C10—H10C0.9600
C4—C101.5080 (19)C11—H11A0.9600
C5—C61.3885 (18)C11—H11B0.9600
C5—H50.9300C11—H11C0.9600
C6—C71.3959 (19)
C1—O2—H2109.5C8—C7—H7119.0
O1—C1—O2122.43 (13)C6—C7—H7119.0
O1—C1—C2124.14 (12)C7—C8—C3119.45 (11)
O2—C1—C2113.42 (10)C7—C8—C9119.81 (12)
C1—C2—C3114.26 (10)C3—C8—C9120.73 (12)
C1—C2—H2A108.7C8—C9—H9A109.5
C3—C2—H2A108.7C8—C9—H9B109.5
C1—C2—H2B108.7H9A—C9—H9B109.5
C3—C2—H2B108.7C8—C9—H9C109.5
H2A—C2—H2B107.6H9A—C9—H9C109.5
C8—C3—C4119.57 (12)H9B—C9—H9C109.5
C8—C3—C2119.34 (11)C4—C10—H10A109.5
C4—C3—C2121.09 (12)C4—C10—H10B109.5
C5—C4—C3119.05 (12)H10A—C10—H10B109.5
C5—C4—C10119.27 (12)C4—C10—H10C109.5
C3—C4—C10121.68 (13)H10A—C10—H10C109.5
C4—C5—C6122.41 (11)H10B—C10—H10C109.5
C4—C5—H5118.8C6—C11—H11A109.5
C6—C5—H5118.8C6—C11—H11B109.5
C5—C6—C7117.54 (12)H11A—C11—H11B109.5
C5—C6—C11120.94 (12)C6—C11—H11C109.5
C7—C6—C11121.52 (13)H11A—C11—H11C109.5
C8—C7—C6121.95 (13)H11B—C11—H11C109.5
O1—C1—C2—C3−18.70 (18)C4—C5—C6—C7−1.7 (2)
O2—C1—C2—C3162.26 (11)C4—C5—C6—C11177.16 (12)
C1—C2—C3—C8−77.82 (15)C5—C6—C7—C81.3 (2)
C1—C2—C3—C4102.58 (14)C11—C6—C7—C8−177.55 (12)
C8—C3—C4—C51.12 (19)C6—C7—C8—C30.3 (2)
C2—C3—C4—C5−179.28 (12)C6—C7—C8—C9−179.59 (12)
C8—C3—C4—C10−178.12 (12)C4—C3—C8—C7−1.50 (19)
C2—C3—C4—C101.48 (19)C2—C3—C8—C7178.89 (11)
C3—C4—C5—C60.5 (2)C4—C3—C8—C9178.36 (12)
C10—C4—C5—C6179.77 (13)C2—C3—C8—C9−1.24 (19)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O2—H2···O1i0.821.842.6564 (15)177

Symmetry codes: (i) −x+1, −y+2, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5261).

References

  • Rigaku/MSC (2005). CrystalClear Rigaku Corporation, Tokyo, Japan.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Thalladi, V. R., Goud, B. S., Hoy, V. J., Allen, F. H., Howard, J. A. K. & Desiraju, G. R. (1996). Chem. Commun. pp. 401–402.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography