2-Mesitylacetic acid

Li, J.-S.; He, Q.-X.; Li, P.-Y.

doi:10.1107/S1600536809051514

organic compounds

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Volume 66| Part 1| January 2010| Page o39

doi:10.1107/S1600536809051514

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2-Mesitylacetic acid

Jiang-Sheng Li,^a ^* Qi-Xi He ^b and Peng-Yu Li ^a

^aSchool of Chemistry and Biological Engineering, Changsha University of Science & Technology, Changsha 410004, People's Republic of China, and ^bCollege of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, People's Republic of China
^*Correspondence e-mail: js_li@yahoo.com.cn

(Received 27 November 2009; accepted 30 November 2009; online 4 December 2009)

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 ).

Experimental

Crystal data

C₁₁H₁₄O₂
M_r = 178.22
Monoclinic, P 2₁ /c
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 ) 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[F² > 2σ(F²)] = 0.035
wR(F²) = 0.104
S = 1.03
1681 reflections
123 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1ⁱ	0.82	1.84	2.6564 (15)	177
Symmetry code: (i) -x+1, -y+2, -z.

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

Supporting information

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

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

checkCIF report

Comment top

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).

Related literature top

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

Experimental top

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).

Computing details top

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

Figures top

	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.

2-Mesitylacetic acid top

Crystal data top

C₁₁H₁₄O₂	F(000) = 384
M_r = 178.22	D_x = 1.238 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 440-442 K K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 8.2312 (16) Å	Cell parameters from 2789 reflections
b = 15.366 (3) Å	θ = 2.5–27.9°
c = 7.5708 (15) Å	µ = 0.08 mm⁻¹
β = 92.74 (3)°	T = 113 K
V = 956.4 (3) Å³	Block, colourless
Z = 4	0.32 × 0.18 × 0.12 mm

Data collection top

Rigaku Saturn CCD diffractometer	1681 independent reflections
Radiation source: rotating anode	1259 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.040
Detector resolution: 7.31 pixels mm^-1	θ_max = 25.0°, θ_min = 2.5°
ω and ϕ scans	h = −9→7
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −18→15
T_min = 0.974, T_max = 0.990	l = −8→8
6163 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.035	H-atom parameters constrained
wR(F²) = 0.104	w = 1/[σ²(F_o²) + (0.0648P)²] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
1681 reflections	Δρ_max = 0.20 e Å⁻³
123 parameters	Δρ_min = −0.18 e Å⁻³
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.109 (9)

Crystal data top

C₁₁H₁₄O₂	V = 956.4 (3) Å³
M_r = 178.22	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.2312 (16) Å	µ = 0.08 mm⁻¹
b = 15.366 (3) Å	T = 113 K
c = 7.5708 (15) Å	0.32 × 0.18 × 0.12 mm
β = 92.74 (3)°

Data collection top

Rigaku Saturn CCD diffractometer	1681 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	1259 reflections with I > 2σ(I)
T_min = 0.974, T_max = 0.990	R_int = 0.040
6163 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.104	H-atom parameters constrained
S = 1.03	Δρ_max = 0.20 e Å⁻³
1681 reflections	Δρ_min = −0.18 e Å⁻³
123 parameters

Special details top

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) top

	x	y	z	U_iso*/U_eq
O1	0.36719 (12)	0.93504 (6)	0.08273 (12)	0.0294 (3)
O2	0.48038 (12)	1.05038 (6)	0.21730 (12)	0.0262 (3)
H2	0.5244	1.0548	0.1228	0.039*
C1	0.38084 (16)	0.98320 (8)	0.21106 (17)	0.0190 (3)
C2	0.29007 (17)	0.97161 (8)	0.37622 (17)	0.0232 (4)
H2A	0.2568	1.0284	0.4173	0.028*
H2B	0.3632	0.9467	0.4669	0.028*
C3	0.14180 (16)	0.91442 (8)	0.35423 (16)	0.0189 (3)
C4	0.14441 (17)	0.82764 (8)	0.41446 (17)	0.0205 (3)
C5	0.00572 (17)	0.77723 (8)	0.38957 (18)	0.0229 (4)
H5	0.0076	0.7201	0.4303	0.027*
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	−0.2313	0.9183	0.1963	0.028*
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	−0.1139	1.0533	0.1566	0.040*
H9B	0.0736	1.0518	0.1289	0.040*
H9C	0.0090	1.0798	0.3119	0.040*
C10	0.29354 (18)	0.78874 (10)	0.50715 (19)	0.0316 (4)
H10A	0.2726	0.7291	0.5360	0.047*
H10B	0.3198	0.8207	0.6136	0.047*
H10C	0.3832	0.7916	0.4308	0.047*
C11	−0.28185 (19)	0.75097 (9)	0.2738 (2)	0.0340 (4)
H11A	−0.2606	0.7100	0.1821	0.051*
H11B	−0.3746	0.7858	0.2382	0.051*
H11C	−0.3035	0.7202	0.3805	0.051*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0363 (7)	0.0287 (6)	0.0241 (6)	−0.0128 (5)	0.0107 (5)	−0.0080 (4)
O2	0.0285 (6)	0.0279 (6)	0.0229 (6)	−0.0113 (4)	0.0080 (4)	−0.0047 (4)
C1	0.0194 (8)	0.0168 (6)	0.0207 (7)	0.0004 (6)	−0.0010 (6)	0.0015 (5)
C2	0.0284 (9)	0.0236 (7)	0.0178 (8)	−0.0039 (6)	0.0027 (6)	−0.0005 (5)
C3	0.0243 (8)	0.0199 (7)	0.0130 (7)	−0.0031 (6)	0.0064 (6)	−0.0029 (5)
C4	0.0250 (8)	0.0212 (7)	0.0159 (7)	0.0019 (6)	0.0061 (6)	−0.0016 (5)
C5	0.0330 (9)	0.0159 (6)	0.0206 (7)	−0.0011 (6)	0.0102 (6)	−0.0005 (5)
C6	0.0259 (9)	0.0253 (7)	0.0188 (7)	−0.0049 (6)	0.0094 (6)	−0.0048 (5)
C7	0.0228 (8)	0.0295 (8)	0.0185 (8)	0.0030 (6)	0.0044 (6)	−0.0018 (5)
C8	0.0270 (8)	0.0190 (7)	0.0141 (7)	0.0001 (6)	0.0073 (6)	−0.0014 (5)
C9	0.0343 (9)	0.0233 (7)	0.0237 (8)	0.0029 (6)	0.0055 (7)	0.0014 (5)
C10	0.0317 (9)	0.0294 (8)	0.0336 (9)	0.0033 (6)	0.0022 (7)	0.0032 (6)
C11	0.0329 (10)	0.0366 (9)	0.0332 (9)	−0.0109 (7)	0.0080 (7)	−0.0040 (6)

Geometric parameters (Å, º) top

O1—C1	1.2222 (15)	C6—C11	1.5037 (18)
O2—C1	1.3174 (15)	C7—C8	1.3865 (18)
O2—H2	0.8200	C7—H7	0.9300
C1—C2	1.4976 (19)	C8—C9	1.5096 (18)
C2—C3	1.5067 (17)	C9—H9A	0.9600
C2—H2A	0.9700	C9—H9B	0.9600
C2—H2B	0.9700	C9—H9C	0.9600
C3—C8	1.4000 (18)	C10—H10A	0.9600
C3—C4	1.4089 (18)	C10—H10B	0.9600
C4—C5	1.3850 (18)	C10—H10C	0.9600
C4—C10	1.5080 (19)	C11—H11A	0.9600
C5—C6	1.3885 (18)	C11—H11B	0.9600
C5—H5	0.9300	C11—H11C	0.9600
C6—C7	1.3959 (19)

C1—O2—H2	109.5	C8—C7—H7	119.0
O1—C1—O2	122.43 (13)	C6—C7—H7	119.0
O1—C1—C2	124.14 (12)	C7—C8—C3	119.45 (11)
O2—C1—C2	113.42 (10)	C7—C8—C9	119.81 (12)
C1—C2—C3	114.26 (10)	C3—C8—C9	120.73 (12)
C1—C2—H2A	108.7	C8—C9—H9A	109.5
C3—C2—H2A	108.7	C8—C9—H9B	109.5
C1—C2—H2B	108.7	H9A—C9—H9B	109.5
C3—C2—H2B	108.7	C8—C9—H9C	109.5
H2A—C2—H2B	107.6	H9A—C9—H9C	109.5
C8—C3—C4	119.57 (12)	H9B—C9—H9C	109.5
C8—C3—C2	119.34 (11)	C4—C10—H10A	109.5
C4—C3—C2	121.09 (12)	C4—C10—H10B	109.5
C5—C4—C3	119.05 (12)	H10A—C10—H10B	109.5
C5—C4—C10	119.27 (12)	C4—C10—H10C	109.5
C3—C4—C10	121.68 (13)	H10A—C10—H10C	109.5
C4—C5—C6	122.41 (11)	H10B—C10—H10C	109.5
C4—C5—H5	118.8	C6—C11—H11A	109.5
C6—C5—H5	118.8	C6—C11—H11B	109.5
C5—C6—C7	117.54 (12)	H11A—C11—H11B	109.5
C5—C6—C11	120.94 (12)	C6—C11—H11C	109.5
C7—C6—C11	121.52 (13)	H11A—C11—H11C	109.5
C8—C7—C6	121.95 (13)	H11B—C11—H11C	109.5

O1—C1—C2—C3	−18.70 (18)	C4—C5—C6—C7	−1.7 (2)
O2—C1—C2—C3	162.26 (11)	C4—C5—C6—C11	177.16 (12)
C1—C2—C3—C8	−77.82 (15)	C5—C6—C7—C8	1.3 (2)
C1—C2—C3—C4	102.58 (14)	C11—C6—C7—C8	−177.55 (12)
C8—C3—C4—C5	1.12 (19)	C6—C7—C8—C3	0.3 (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—C10	1.48 (19)	C2—C3—C8—C7	178.89 (11)
C3—C4—C5—C6	0.5 (2)	C4—C3—C8—C9	178.36 (12)
C10—C4—C5—C6	179.77 (13)	C2—C3—C8—C9	−1.24 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1ⁱ	0.82	1.84	2.6564 (15)	177

Symmetry code: (i) −x+1, −y+2, −z.

Experimental details

Crystal data
Chemical formula	C₁₁H₁₄O₂
M_r	178.22
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	113
a, b, c (Å)	8.2312 (16), 15.366 (3), 7.5708 (15)
β (°)	92.74 (3)
V (Å³)	956.4 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.32 × 0.18 × 0.12

Data collection
Diffractometer	Rigaku Saturn CCD diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2005)
T_min, T_max	0.974, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	6163, 1681, 1259
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.104, 1.03
No. of reflections	1681
No. of parameters	123
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.18

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1ⁱ	0.82	1.84	2.6564 (15)	177

Symmetry code: (i) −x+1, −y+2, −z.

References

Rigaku/MSC (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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. CSD CrossRef Web of Science Google Scholar

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CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 1| January 2010| Page o39

doi:10.1107/S1600536809051514

Open

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