1-(3-tert-Butyl-4-hy­droxy­phen­yl)ethanone

Miao, H.-M.; Zhao, G.-L.; Shao, H.; Wang, J.-W.

doi:10.1107/S1600536810027339

organic compounds

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Volume 66| Part 8| August 2010| Page o2037

https://doi.org/10.1107/S1600536810027339

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1-(3-tert-Butyl-4-hydroxyphenyl)ethanone

Hua-Ming Miao,^a Gui-Long Zhao,^b Hua Shao ^b and Jian-Wu Wang ^a ^*

^aSchool of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, People's Republic of China, and ^bTianjin Key Laboratory of Molecular Design and Drug Discovery, Tianjin Institute of Pharmaceutical Research, Tianjin 300193, People's Republic of China
^*Correspondence e-mail: yugp2005@yahoo.com.cn

(Received 7 July 2010; accepted 9 July 2010; online 17 July 2010)

The title compound, C₁₂H₁₆O₂, is approximately planar (r.m.s. deviation = 0.030 Å), apart from two methyl groups of the tert-butyl unit [deviations of the C atoms = 1.140 (2) and −1.367 (1) Å]. In the crystal, intermolecular O—H⋯O hydrogen bonds link the molecules into hexameric rings with R₆⁶(48) graph-set motifs.

Related literature

For details of the biological activity of the PAR-1 antagonist, see: Chackalamannil (2006 ); Shimomura et al. (2006 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₂H₁₆O₂
M_r = 192.25
Trigonal, $[R \overline 3]$
a = 24.019 (3) Å
c = 9.999 (2) Å
V = 4995.8 (14) Å³
Z = 18
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 113 K
0.20 × 0.18 × 0.14 mm

Data collection

Rigaku Saturn CCD diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.985, T_max = 0.989
12180 measured reflections
1950 independent reflections
1733 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.110
S = 1.03
1950 reflections
133 parameters
H-atom parameters constrained
Δρ_max = 0.24 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
O1—H1⋯O2ⁱ	0.84	1.83	2.6624 (12)	171
Symmetry code: (i) y, -x+y+1, -z+2.

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

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810027339/hb5546sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810027339/hb5546Isup2.hkl

checkCIF report

Comment top

PAR-1 antagonist is a kind of new anti-platelet agents in the antithrombotic area for the treat of artery coronary syndrome (Chackalamannil, 2006). The title compound is prepared when the well established PAR-1 antagonist E-5555 was synthesized as positive control during the development of our own PAR-1 antagonists (Shimomura et al., 2006).

In title compound, C₁₂H₁₆O₂, bond lengths are normal ((Allen et al., 1987)). Intermolecular interactions O—H···O hydrogen bonds link the moleculars into hexamer.

Related literature top

For details of the biological activity of the PAR-1 antagonist, see: Chackalamannil (2006); Shimomura et al. (2006). For bond-length data, see: Allen et al. (1987).

Experimental top

A dried 500-ml round-bottomed flask was charged with 21.33 g (0.160 mol, 1.2 eq) of anhydrous aluminium chloride and 400 ml of dried toluene, and the resulting yellow slurry was stirred and cooled to -35°C followed by dropwise addition of 20.0 g (0.133 mol, 1.0 eq) of 2-(tert-butyl)phenol dissolved in 20 ml of dried toluene. To the yellow clear solution obtained above was added dropwise 12.56 g (0.160 mol, 1.2 eq) of acetyl chloride dissolved in 20 ml of dried toluene, and after addition the resulting mixture (a yellow clear solution) was stirred at this temperature until all the starting material was consumed almost completely as indicated by TLC analysis (typical 2–3 h). The reaction mixture was slowly poured into 500 ml of stirred ice-water with great care, and the resulting mixture was stirred. The organic phase was separated and the aqueous phase was exacted with three 100-ml portions of ethyl acetate. The combined exacts were washed with brine to pH = 7, dried over sodium sulfate and evaporated on a rotary evaporator to afford the crude product as colorless crystals, which was triturated with ethyl acetate/petroleum ether (1/30) to afford the pure product as colorless crystals. Colourless blocks of (I) were obtained via slow evaporation at room temperature of a solution of the pure title compound in ethyl acetate/petroleum ether (1/30).

Structure description top

In title compound, C₁₂H₁₆O₂, bond lengths are normal ((Allen et al., 1987)). Intermolecular interactions O—H···O hydrogen bonds link the moleculars into hexamer.

For details of the biological activity of the PAR-1 antagonist, see: Chackalamannil (2006); Shimomura et al. (2006). For bond-length data, see: Allen et al. (1987).

Computing details top

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

Figures top

	Fig. 1. View of (I), with displacement ellipsoids drawn at the 40% probability level.
	Fig. 2. View of the hexameric ring in the crystal of (I).

1-(3-tert-Butyl-4-hydroxyphenyl)ethanone top

Crystal data top

C₁₂H₁₆O₂	D_x = 1.150 Mg m⁻³
M_r = 192.25	Mo Kα radiation, λ = 0.71073 Å
Trigonal, R3	Cell parameters from 5019 reflections
Hall symbol: -R 3	θ = 2.3–27.9°
a = 24.019 (3) Å	µ = 0.08 mm⁻¹
c = 9.999 (2) Å	T = 113 K
V = 4995.8 (14) Å³	Block, colorless
Z = 18	0.20 × 0.18 × 0.14 mm
F(000) = 1872

Data collection top

Rigaku Saturn CCD diffractometer	1950 independent reflections
Radiation source: rotating anode	1733 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.034
Detector resolution: 7.31 pixels mm^-1	θ_max = 25.0°, θ_min = 1.7°
ω and φ scans	h = −21→28
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −28→28
T_min = 0.985, T_max = 0.989	l = −11→11
12180 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)] = 0.039	H-atom parameters constrained
wR(F²) = 0.110	w = 1/[σ²(F_o²) + (0.0723P)² + 1.6812P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.002
1950 reflections	Δρ_max = 0.24 e Å⁻³
133 parameters	Δρ_min = −0.18 e Å⁻³
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0080 (7)

Crystal data top

C₁₂H₁₆O₂	Z = 18
M_r = 192.25	Mo Kα radiation
Trigonal, R3	µ = 0.08 mm⁻¹
a = 24.019 (3) Å	T = 113 K
c = 9.999 (2) Å	0.20 × 0.18 × 0.14 mm
V = 4995.8 (14) Å³

Data collection top

Rigaku Saturn CCD diffractometer	1950 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	1733 reflections with I > 2σ(I)
T_min = 0.985, T_max = 0.989	R_int = 0.034
12180 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.110	H-atom parameters constrained
S = 1.03	Δρ_max = 0.24 e Å⁻³
1950 reflections	Δρ_min = −0.18 e Å⁻³
133 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	0.57494 (4)	0.80946 (4)	0.95585 (9)	0.0304 (3)
H1	0.6049	0.8470	0.9716	0.046*
O2	0.72860 (4)	0.66048 (4)	0.99295 (9)	0.0296 (3)
C1	0.59747 (6)	0.76811 (5)	0.96507 (12)	0.0230 (3)
C2	0.66314 (6)	0.79128 (5)	0.98477 (12)	0.0248 (3)
H2	0.6918	0.8362	0.9924	0.030*
C3	0.68665 (6)	0.74960 (6)	0.99315 (11)	0.0241 (3)
H3	0.7315	0.7658	1.0036	0.029*
C4	0.64445 (5)	0.68348 (5)	0.98621 (11)	0.0215 (3)
C5	0.57896 (5)	0.66128 (5)	0.96739 (11)	0.0214 (3)
H5	0.5504	0.6162	0.9639	0.026*
C6	0.55354 (5)	0.70158 (5)	0.95352 (11)	0.0213 (3)
C7	0.48199 (6)	0.67589 (6)	0.92360 (13)	0.0272 (3)
C8	0.45154 (6)	0.69730 (7)	1.03216 (15)	0.0386 (4)
H8A	0.4588	0.6840	1.1201	0.058*
H8B	0.4052	0.6773	1.0159	0.058*
H8C	0.4711	0.7442	1.0299	0.058*
C9	0.47547 (7)	0.70091 (7)	0.78650 (14)	0.0395 (4)
H9A	0.4980	0.7480	0.7879	0.059*
H9B	0.4299	0.6843	0.7666	0.059*
H9C	0.4943	0.6864	0.7175	0.059*
C10	0.44439 (6)	0.60217 (6)	0.91906 (15)	0.0373 (4)
H10A	0.4622	0.5871	0.8489	0.056*
H10B	0.3991	0.5872	0.8997	0.056*
H10C	0.4479	0.5851	1.0057	0.056*
C11	0.67018 (6)	0.63918 (6)	0.99456 (11)	0.0236 (3)
C12	0.62460 (6)	0.56802 (6)	1.00527 (13)	0.0297 (3)
H12A	0.6491	0.5459	1.0191	0.045*
H12B	0.5995	0.5524	0.9227	0.045*
H12C	0.5955	0.5593	1.0811	0.045*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0294 (5)	0.0171 (4)	0.0472 (6)	0.0134 (4)	−0.0021 (4)	0.0000 (4)
O2	0.0260 (5)	0.0321 (5)	0.0356 (5)	0.0182 (4)	−0.0016 (4)	0.0001 (4)
C1	0.0287 (7)	0.0206 (6)	0.0224 (6)	0.0144 (5)	0.0003 (5)	0.0014 (5)
C2	0.0263 (6)	0.0177 (6)	0.0270 (6)	0.0083 (5)	−0.0023 (5)	−0.0010 (5)
C3	0.0223 (6)	0.0261 (6)	0.0230 (6)	0.0113 (5)	−0.0026 (5)	−0.0003 (5)
C4	0.0251 (6)	0.0224 (6)	0.0186 (6)	0.0131 (5)	−0.0005 (4)	0.0003 (4)
C5	0.0249 (6)	0.0184 (6)	0.0210 (6)	0.0109 (5)	0.0003 (5)	0.0004 (4)
C6	0.0240 (6)	0.0200 (6)	0.0204 (6)	0.0115 (5)	0.0008 (5)	0.0002 (4)
C7	0.0230 (6)	0.0218 (6)	0.0385 (7)	0.0126 (5)	−0.0013 (5)	−0.0007 (5)
C8	0.0294 (7)	0.0303 (7)	0.0577 (9)	0.0163 (6)	0.0115 (6)	0.0026 (6)
C9	0.0362 (8)	0.0395 (8)	0.0461 (8)	0.0215 (7)	−0.0152 (6)	−0.0038 (6)
C10	0.0220 (7)	0.0252 (7)	0.0626 (9)	0.0102 (6)	−0.0031 (6)	−0.0050 (6)
C11	0.0271 (7)	0.0288 (7)	0.0188 (6)	0.0169 (5)	−0.0015 (5)	−0.0003 (5)
C12	0.0310 (7)	0.0257 (7)	0.0385 (7)	0.0188 (6)	−0.0017 (5)	0.0013 (5)

Geometric parameters (Å, º) top

O1—C1	1.3512 (14)	C7—C10	1.5343 (17)
O1—H1	0.8400	C7—C9	1.5359 (19)
O2—C11	1.2299 (14)	C8—H8A	0.9800
C1—C2	1.3995 (17)	C8—H8B	0.9800
C1—C6	1.4121 (16)	C8—H8C	0.9800
C2—C3	1.3761 (17)	C9—H9A	0.9800
C2—H2	0.9500	C9—H9B	0.9800
C3—C4	1.3944 (17)	C9—H9C	0.9800
C3—H3	0.9500	C10—H10A	0.9800
C4—C5	1.3983 (16)	C10—H10B	0.9800
C4—C11	1.4762 (16)	C10—H10C	0.9800
C5—C6	1.3857 (16)	C11—C12	1.5034 (17)
C5—H5	0.9500	C12—H12A	0.9800
C6—C7	1.5372 (16)	C12—H12B	0.9800
C7—C8	1.5342 (18)	C12—H12C	0.9800

C1—O1—H1	109.5	C7—C8—H8B	109.5
O1—C1—C2	120.22 (10)	H8A—C8—H8B	109.5
O1—C1—C6	118.61 (10)	C7—C8—H8C	109.5
C2—C1—C6	121.16 (10)	H8A—C8—H8C	109.5
C3—C2—C1	120.68 (10)	H8B—C8—H8C	109.5
C3—C2—H2	119.7	C7—C9—H9A	109.5
C1—C2—H2	119.7	C7—C9—H9B	109.5
C2—C3—C4	119.76 (10)	H9A—C9—H9B	109.5
C2—C3—H3	120.1	C7—C9—H9C	109.5
C4—C3—H3	120.1	H9A—C9—H9C	109.5
C3—C4—C5	118.66 (10)	H9B—C9—H9C	109.5
C3—C4—C11	119.35 (10)	C7—C10—H10A	109.5
C5—C4—C11	121.96 (10)	C7—C10—H10B	109.5
C6—C5—C4	123.49 (10)	H10A—C10—H10B	109.5
C6—C5—H5	118.3	C7—C10—H10C	109.5
C4—C5—H5	118.3	H10A—C10—H10C	109.5
C5—C6—C1	116.18 (10)	H10B—C10—H10C	109.5
C5—C6—C7	122.26 (10)	O2—C11—C4	120.07 (11)
C1—C6—C7	121.54 (10)	O2—C11—C12	120.31 (10)
C8—C7—C10	107.67 (10)	C4—C11—C12	119.62 (10)
C8—C7—C9	109.96 (11)	C11—C12—H12A	109.5
C10—C7—C9	107.98 (11)	C11—C12—H12B	109.5
C8—C7—C6	110.64 (10)	H12A—C12—H12B	109.5
C10—C7—C6	111.33 (10)	C11—C12—H12C	109.5
C9—C7—C6	109.21 (10)	H12A—C12—H12C	109.5
C7—C8—H8A	109.5	H12B—C12—H12C	109.5

O1—C1—C2—C3	−179.44 (11)	C2—C1—C6—C7	−176.33 (11)
C6—C1—C2—C3	0.13 (18)	C5—C6—C7—C8	122.54 (12)
C1—C2—C3—C4	−2.04 (18)	C1—C6—C7—C8	−59.10 (15)
C2—C3—C4—C5	1.59 (17)	C5—C6—C7—C10	2.85 (16)
C2—C3—C4—C11	179.67 (10)	C1—C6—C7—C10	−178.79 (11)
C3—C4—C5—C6	0.82 (18)	C5—C6—C7—C9	−116.30 (12)
C11—C4—C5—C6	−177.21 (10)	C1—C6—C7—C9	62.07 (14)
C4—C5—C6—C1	−2.62 (17)	C3—C4—C11—O2	−7.86 (17)
C4—C5—C6—C7	175.82 (11)	C5—C4—C11—O2	170.15 (11)
O1—C1—C6—C5	−178.30 (10)	C3—C4—C11—C12	172.03 (10)
C2—C1—C6—C5	2.13 (17)	C5—C4—C11—C12	−9.95 (17)
O1—C1—C6—C7	3.25 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱ	0.84	1.83	2.6624 (12)	171

Symmetry code: (i) y, −x+y+1, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₂H₁₆O₂
M_r	192.25
Crystal system, space group	Trigonal, R3
Temperature (K)	113
a, c (Å)	24.019 (3), 9.999 (2)
V (Å³)	4995.8 (14)
Z	18
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.20 × 0.18 × 0.14

Data collection
Diffractometer	Rigaku Saturn CCD
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.985, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections	12180, 1950, 1733
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.110, 1.03
No. of reflections	1950
No. of parameters	133
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.18

Computer programs: CrystalClear (Rigaku, 2005), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱ	0.84	1.83	2.6624 (12)	171

Symmetry code: (i) y, −x+y+1, −z+2.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CSD CrossRef Web of Science Google Scholar
Chackalamannil, S. (2006). J. Med. Chem. 49, 5389–5403. Web of Science CrossRef PubMed CAS Google Scholar
Rigaku. (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
Shimomura, N., Sasho, M., Kayano, A., Yoshizawa, K., Tsujii, M., Kuroda, H. & Furukawa, K. (2006). US Patent 20060058370. Google Scholar

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CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 8| August 2010| Page o2037

https://doi.org/10.1107/S1600536810027339

Open

access