(4-tert-Butyl­phenyl)­acetic acid

Liu, B.-X.; Yu, Y.-P.; Xu, D.-J.

doi:10.1107/S160053680802802X

organic compounds

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Volume 64| Part 10| October 2008| Page o1971

doi:10.1107/S160053680802802X

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(4-tert-Butylphenyl)acetic acid

Bing-Xin Liu,^a Yan-Ping Yu ^a and Duan-Jun Xu ^b ^*

^aDepartment of Chemistry, Shanghai University, People's Republic of China, and ^bDepartment of Chemistry, Zhejiang University, People's Republic of China
^*Correspondence e-mail: xudj@mail.hz.zj.cn

(Received 17 July 2008; accepted 2 September 2008; online 20 September 2008)

In the title compound, C₁₂H₁₆O₂, the plane of the carboxylic acid group is almost perpendicular to the benzene ring [dihedral angle 80.9 (3)°] and the tert-butyl unit is disordered over two sets of sites in a 0.503 (6):0.497 (6) ratio. In the crystal structure, centrosymmetric dimers arise from pairs of O—H⋯O hydrogen bonds involving the carboxylic acid groups.

Related literature

For general background, see: Liu et al. (2006 ). For a related structure, see: van Koningsveld (1982 ).

Experimental

Crystal data

C₁₂H₁₆O₂
M_r = 192.25
Monoclinic, C 2/c
a = 11.209 (2) Å
b = 12.442 (3) Å
c = 17.250 (5) Å
β = 104.625 (12)°
V = 2327.8 (10) Å³
Z = 8
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 295 (2) K
0.30 × 0.23 × 0.16 mm

Data collection

Bruker APEX CCD diffractometer
Absorption correction: none
5829 measured reflections
2047 independent reflections
1375 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.074
wR(F²) = 0.220
S = 1.06
2047 reflections
131 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2ⁱ	0.92	1.74	2.659 (3)	176
Symmetry code: (i) $[-x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]$ .

Data collection: SMART (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680802802X/hb2766sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680802802X/hb2766Isup2.hkl

checkCIF report

Comment top

As part of investigation on the nature of aromatic stacking (Liu et al., 2006), the title compound, (I), has recently been prepared in Prof. Liu's laboratory by the hydrolization reaction of 2-(4-tert-butylphenyl)-1-morpholinoethanethione. Herein we present its X-ray structure (Fig. 1).

The C8—O1 bond distance of 1.309 (3) Å is significantly longer than the C8—O2 bond distance of 1.191 (3) Å. The carboxyl group is nearly perpendicular to the benzene plane, the dihedral angle being 80.9 (3)°. The adjacent molecules are linked together via O—H···O hydrogen bonding (Table 1) to form a centrosymmetric supramolecular dimer as shown in Fig. 2, which is comparable to that found in 4-tert-butylbenzoic acid (van Koningsveld, 1982).

Related literature top

For general background, see: Liu et al. (2006). For a related structure, see: van Koningsveld (1982).

Experimental top

The title compound was prepared by a hydrolization reaction of 2-(4-tert-butylphenyl)-1-morpholinoethanethione (55 g) in a solution containing CH₃COOH (150 ml), H₂SO₄ (25 ml, 98%) and water (30 ml) at 390 K until the reaction mixture changed colour to dark-green. After cooling to room temperature, the solid product was separated from the reaction mixture, and colourless prisms of (I) were obtained by recrystallization of the solid product from an ethanol–water solution (1:1 v/v) after 2 months.

Computing details top

Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular structure of (I) with 30% probability displacement ellipsoids (arbitrary spheres for H atoms). Double dashed lines indicate one of disordered components.
	Fig. 2. The unit cell packing diagram showing the supra-molecular dimeric structure linked by the hydrogen bonding (dashed lines).

(4-tert-Butylphenyl)acetic acid top

Crystal data top

C₁₂H₁₆O₂	F(000) = 832
M_r = 192.25	D_x = 1.097 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2180 reflections
a = 11.209 (2) Å	θ = 2.8–25.0°
b = 12.442 (3) Å	µ = 0.07 mm⁻¹
c = 17.250 (5) Å	T = 295 K
β = 104.625 (12)°	Prism, colourless
V = 2327.8 (10) Å³	0.30 × 0.23 × 0.16 mm
Z = 8

Data collection top

Bruker APEXII CCD diffractometer	1375 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.025
Graphite monochromator	θ_max = 25.0°, θ_min = 2.4°
Detector resolution: 10 pixels mm^-1	h = −13→12
ϕ and ω scans	k = −11→14
5829 measured reflections	l = −20→17
2047 independent reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.075	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.220	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0943P)² + 2.2585P] where P = (F_o² + 2F_c²)/3
2047 reflections	(Δ/σ)_max = 0.003
131 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₁₂H₁₆O₂	V = 2327.8 (10) Å³
M_r = 192.25	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 11.209 (2) Å	µ = 0.07 mm⁻¹
b = 12.442 (3) Å	T = 295 K
c = 17.250 (5) Å	0.30 × 0.23 × 0.16 mm
β = 104.625 (12)°

Data collection top

Bruker APEXII CCD diffractometer	1375 reflections with I > 2σ(I)
5829 measured reflections	R_int = 0.025
2047 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.075	0 restraints
wR(F²) = 0.220	H-atom parameters constrained
S = 1.06	Δρ_max = 0.30 e Å⁻³
2047 reflections	Δρ_min = −0.25 e Å⁻³
131 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	Occ. (<1)
O1	0.3924 (2)	0.7974 (2)	0.56682 (15)	0.1086 (10)
H1	0.3088	0.7959	0.5607	0.163*
O2	0.35115 (18)	0.70221 (19)	0.45614 (13)	0.0801 (7)
C1	0.6042 (2)	0.6780 (3)	0.45859 (19)	0.0733 (9)
C2	0.6468 (3)	0.5756 (3)	0.4707 (2)	0.0904 (11)
H2	0.6448	0.5403	0.5179	0.108*
C3	0.6930 (3)	0.5233 (3)	0.41409 (19)	0.0838 (10)
H3	0.7216	0.4532	0.4244	0.101*
C4	0.6984 (2)	0.5702 (2)	0.34325 (15)	0.0582 (7)
C5	0.6512 (3)	0.6719 (3)	0.33048 (18)	0.0714 (9)
H5	0.6498	0.7060	0.2823	0.086*
C6	0.6056 (3)	0.7253 (3)	0.3870 (2)	0.0819 (10)
H6	0.5753	0.7948	0.3764	0.098*
C7	0.5608 (3)	0.7390 (4)	0.5219 (2)	0.1051 (14)
H7A	0.5971	0.7062	0.5735	0.126*
H7B	0.5917	0.8120	0.5237	0.126*
C8	0.4244 (3)	0.7432 (3)	0.51024 (17)	0.0653 (8)
C9	0.7547 (3)	0.5128 (3)	0.28348 (18)	0.0732 (9)
C10A	0.8271 (11)	0.6028 (9)	0.2430 (6)	0.1125 (15)	0.497 (6)
H10A	0.8575	0.5698	0.2015	0.169*	0.497 (6)
H10B	0.8950	0.6315	0.2833	0.169*	0.497 (6)
H10C	0.7713	0.6598	0.2207	0.169*	0.497 (6)
C11A	0.8538 (13)	0.4343 (11)	0.3166 (9)	0.1125 (15)	0.497 (6)
H11A	0.8187	0.3714	0.3344	0.169*	0.497 (6)
H11B	0.9124	0.4660	0.3611	0.169*	0.497 (6)
H11C	0.8944	0.4147	0.2759	0.169*	0.497 (6)
C12A	0.6605 (9)	0.4711 (9)	0.2153 (6)	0.1125 (15)	0.497 (6)
H12A	0.6206	0.5299	0.1829	0.169*	0.497 (6)
H12B	0.6006	0.4309	0.2344	0.169*	0.497 (6)
H12C	0.6985	0.4251	0.1838	0.169*	0.497 (6)
C10B	0.7561 (11)	0.5733 (9)	0.2101 (6)	0.1125 (15)	0.503 (6)
H10D	0.7923	0.5297	0.1761	0.169*	0.503 (6)
H10E	0.8037	0.6377	0.2243	0.169*	0.503 (6)
H10F	0.6732	0.5917	0.1823	0.169*	0.503 (6)
C11B	0.8802 (13)	0.4692 (11)	0.3269 (8)	0.1125 (15)	0.503 (6)
H11D	0.8717	0.4232	0.3698	0.169*	0.503 (6)
H11E	0.9342	0.5279	0.3482	0.169*	0.503 (6)
H11F	0.9142	0.4289	0.2900	0.169*	0.503 (6)
C12B	0.6679 (9)	0.4091 (9)	0.2531 (6)	0.1125 (15)	0.503 (6)
H12D	0.5836	0.4318	0.2348	0.169*	0.503 (6)
H12E	0.6756	0.3592	0.2965	0.169*	0.503 (6)
H12F	0.6931	0.3750	0.2099	0.169*	0.503 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0599 (14)	0.172 (3)	0.0991 (17)	−0.0057 (14)	0.0303 (12)	−0.0708 (17)
O2	0.0532 (12)	0.1151 (18)	0.0758 (14)	−0.0020 (11)	0.0231 (10)	−0.0310 (12)
C1	0.0408 (15)	0.112 (3)	0.0682 (19)	0.0018 (15)	0.0160 (13)	−0.0220 (18)
C2	0.098 (3)	0.114 (3)	0.068 (2)	0.007 (2)	0.0381 (19)	0.0096 (19)
C3	0.105 (3)	0.078 (2)	0.078 (2)	0.0180 (19)	0.0417 (19)	0.0145 (17)
C4	0.0506 (15)	0.0689 (17)	0.0574 (15)	0.0100 (13)	0.0178 (12)	0.0069 (13)
C5	0.0659 (18)	0.084 (2)	0.0675 (18)	0.0235 (16)	0.0221 (14)	0.0174 (15)
C6	0.064 (2)	0.086 (2)	0.094 (2)	0.0292 (16)	0.0180 (17)	−0.0029 (18)
C7	0.0542 (19)	0.171 (4)	0.091 (2)	0.003 (2)	0.0214 (17)	−0.053 (3)
C8	0.0546 (17)	0.086 (2)	0.0594 (16)	0.0042 (14)	0.0218 (14)	−0.0110 (15)
C9	0.0687 (19)	0.091 (2)	0.0630 (17)	0.0215 (16)	0.0231 (15)	0.0022 (16)
C10A	0.116 (3)	0.136 (4)	0.098 (3)	0.029 (3)	0.050 (3)	−0.008 (2)
C11A	0.116 (3)	0.136 (4)	0.098 (3)	0.029 (3)	0.050 (3)	−0.008 (2)
C12A	0.116 (3)	0.136 (4)	0.098 (3)	0.029 (3)	0.050 (3)	−0.008 (2)
C10B	0.116 (3)	0.136 (4)	0.098 (3)	0.029 (3)	0.050 (3)	−0.008 (2)
C11B	0.116 (3)	0.136 (4)	0.098 (3)	0.029 (3)	0.050 (3)	−0.008 (2)
C12B	0.116 (3)	0.136 (4)	0.098 (3)	0.029 (3)	0.050 (3)	−0.008 (2)

Geometric parameters (Å, º) top

O1—C8	1.309 (3)	C9—C11B	1.517 (15)
O1—H1	0.9169	C9—C12B	1.621 (11)
O2—C8	1.191 (3)	C9—C10A	1.639 (11)
C1—C2	1.358 (5)	C10A—H10A	0.9600
C1—C6	1.371 (5)	C10A—H10B	0.9600
C1—C7	1.508 (4)	C10A—H10C	0.9600
C2—C3	1.379 (4)	C11A—H11A	0.9600
C2—H2	0.9300	C11A—H11B	0.9600
C3—C4	1.369 (4)	C11A—H11C	0.9600
C3—H3	0.9300	C12A—H12A	0.9600
C4—C5	1.368 (4)	C12A—H12B	0.9600
C4—C9	1.517 (4)	C12A—H12C	0.9600
C5—C6	1.381 (4)	C10B—H10D	0.9600
C5—H5	0.9300	C10B—H10E	0.9600
C6—H6	0.9300	C10B—H10F	0.9600
C7—C8	1.491 (4)	C11B—H11D	0.9600
C7—H7A	0.9700	C11B—H11E	0.9600
C7—H7B	0.9700	C11B—H11F	0.9600
C9—C12A	1.463 (10)	C12B—H12D	0.9600
C9—C10B	1.476 (10)	C12B—H12E	0.9600
C9—C11A	1.480 (15)	C12B—H12F	0.9600

C8—O1—H1	111.6	C10B—C9—C12B	105.3 (5)
C2—C1—C6	117.3 (3)	C4—C9—C12B	106.0 (4)
C2—C1—C7	121.7 (3)	C11B—C9—C12B	106.3 (6)
C6—C1—C7	121.0 (4)	C12A—C9—C10A	103.5 (6)
C1—C2—C3	120.9 (3)	C11A—C9—C10A	102.2 (7)
C1—C2—H2	119.5	C4—C9—C10A	107.7 (4)
C3—C2—H2	119.5	C9—C10A—H10A	109.5
C4—C3—C2	122.7 (3)	C9—C10A—H10B	109.5
C4—C3—H3	118.7	C9—C10A—H10C	109.5
C2—C3—H3	118.7	C9—C11A—H11A	109.5
C5—C4—C3	115.8 (3)	C9—C11A—H11B	109.5
C5—C4—C9	122.4 (3)	C9—C11A—H11C	109.5
C3—C4—C9	121.7 (3)	C9—C12A—H12A	109.5
C4—C5—C6	121.9 (3)	C9—C12A—H12B	109.5
C4—C5—H5	119.0	C9—C12A—H12C	109.5
C6—C5—H5	119.0	C9—C10B—H10D	109.5
C1—C6—C5	121.3 (3)	C9—C10B—H10E	109.5
C1—C6—H6	119.4	H10D—C10B—H10E	109.5
C5—C6—H6	119.4	C9—C10B—H10F	109.5
C8—C7—C1	115.3 (3)	H10D—C10B—H10F	109.5
C8—C7—H7A	108.5	H10E—C10B—H10F	109.5
C1—C7—H7A	108.5	C9—C11B—H11D	109.5
C8—C7—H7B	108.5	C9—C11B—H11E	109.5
C1—C7—H7B	108.5	H11D—C11B—H11E	109.5
H7A—C7—H7B	107.5	C9—C11B—H11F	109.5
O2—C8—O1	122.7 (3)	H11D—C11B—H11F	109.5
O2—C8—C7	124.9 (3)	H11E—C11B—H11F	109.5
O1—C8—C7	112.4 (3)	C9—C12B—H12D	109.5
C12A—C9—C11A	113.3 (6)	C9—C12B—H12E	109.5
C12A—C9—C4	112.0 (4)	H12D—C12B—H12E	109.5
C10B—C9—C4	116.0 (4)	C9—C12B—H12F	109.5
C11A—C9—C4	116.6 (6)	H12D—C12B—H12F	109.5
C10B—C9—C11B	113.3 (7)	H12E—C12B—H12F	109.5
C4—C9—C11B	109.0 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱ	0.92	1.74	2.659 (3)	176

Symmetry code: (i) −x+1/2, −y+3/2, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₂H₁₆O₂
M_r	192.25
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	295
a, b, c (Å)	11.209 (2), 12.442 (3), 17.250 (5)
β (°)	104.625 (12)
V (Å³)	2327.8 (10)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.30 × 0.23 × 0.16

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	5829, 2047, 1375
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.075, 0.220, 1.06
No. of reflections	2047
No. of parameters	131
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.25

Computer programs: SMART (Bruker, 2004), SAINT (Bruker, 2004), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱ	0.92	1.74	2.659 (3)	176

Symmetry code: (i) −x+1/2, −y+3/2, −z+1.

Acknowledgements

This project was supported by the Educational Development Foundation of Shanghai Educational Committee, China (No. AB0448).

References

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