4-(4-Hy­droxy­phen­yl)butan-2-one

Wang, J.-G.

doi:10.1107/S1600536811017272

organic compounds

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Volume 67| Part 6| June 2011| Page o1411

doi:10.1107/S1600536811017272

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4-(4-Hydroxyphenyl)butan-2-one

Jian-Guo Wang ^a ^*

^aSchool of Chemistry & Chemical Engineering, Jiujiang University, Jiujiang 332005, People's Republic of China
^*Correspondence e-mail: jgwang117@163.com

(Received 28 April 2011; accepted 7 May 2011; online 14 May 2011)

In the title compound, C₁₀H₁₂O₂, the substituted benzene ring is inclined at a dihedral angle of 75.9 (1)° to the almost planar butan-2-one substituent (r.m.s. deviation = 0.02 Å). In the crystal, intermolecular O—H⋯O hydrogen bonds link the molecules into chains along the a axis.

Related literature

For the odour threshold of the title compound, see: Larsen & Poll (1990 ); Tang (2006 ). For a related structure, see: Kosjek et al. (2003 ). For the synthesis, see: Smith (1996 ).

Experimental

Crystal data

C₁₀H₁₂O₂
M_r = 164.20
Orthorhombic, P n a 2₁
a = 14.0242 (13) Å
b = 12.4450 (12) Å
c = 5.2706 (5) Å
V = 919.88 (15) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 298 K
0.23 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
5687 measured reflections
1797 independent reflections
1678 reflections with I > 2σ(I)
R_int = 0.101

Refinement

R[F² > 2σ(F²)] = 0.064
wR(F²) = 0.173
S = 1.06
1797 reflections
113 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2ⁱ	0.91 (5)	1.97 (5)	2.842 (4)	161 (5)
Symmetry code: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-1]$ .

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; 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: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811017272/sj5132sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811017272/sj5132Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811017272/sj5132Isup3.cml

checkCIF report

Comment top

The title compound, known as raspberry ketone, was originally extracted from raspberry and possesses the flavour of raspberries (Larsen & Poll 1990). However, the content of raspberry ketone in raspberry is very low (Tang, 2006).

The asymmetric unit of (I) contains one independent molecule (Fig. 1). The bond lengths and angles are normal and similar to those in a related structure (Kosjek et al., 2003; Smith, 1996). The hydroxy substituted C1···C6 benzene ring is inclined at a dihedral angle of 75.9 (1)° from the planar C7···C10(O2) butan-2-one substituent (rms deviation 0.02Å). In the crystal structure, a one-dimensional network structure (Fig. 2) is formed by intermolecular O—H···O hydrogen bonds (Table 1).

Related literature top

For the odour threshold of the title compound, see: Larsen & Poll (1990); Tang (2006). For a related structure, see: Kosjek et al. (2003). For the synthesis, see: Smith (1996).

Experimental top

The title compound was synthesized according to a reported procedure from the corresponding p-hydroxybenzaldehyde (Smith, 1996). After recrystallisation from ethanol, the title compound was dissolved in dilute aqeous NaOH. Hydrochloric acid 1:1 (v/v) was slowly added to adjust to pH = 5. The mixture was left for a week after which colourless block-like crystals were obtained.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. View of the molecule of (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. The crystal packing for (I), with O—H···O interactions shown as dashed lines.

4-(4-Hydroxyphenyl)butan-2-one top

Crystal data top

C₁₀H₁₂O₂	F(000) = 352
M_r = 164.20	D_x = 1.186 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 2580 reflections
a = 14.0242 (13) Å	θ = 2.2–24.5°
b = 12.4450 (12) Å	µ = 0.08 mm⁻¹
c = 5.2706 (5) Å	T = 298 K
V = 919.88 (15) Å³	Block, colourless
Z = 4	0.23 × 0.20 × 0.20 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	1678 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.101
Graphite monochromator	θ_max = 26.0°, θ_min = 2.2°
ϕ and ω scans	h = −16→17
5687 measured reflections	k = −12→15
1797 independent reflections	l = −6→6

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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.173	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.1055P)² + 0.082P] where P = (F_o² + 2F_c²)/3
1797 reflections	(Δ/σ)_max < 0.001
113 parameters	Δρ_max = 0.21 e Å⁻³
1 restraint	Δρ_min = −0.15 e Å⁻³

Crystal data top

C₁₀H₁₂O₂	V = 919.88 (15) Å³
M_r = 164.20	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 14.0242 (13) Å	µ = 0.08 mm⁻¹
b = 12.4450 (12) Å	T = 298 K
c = 5.2706 (5) Å	0.23 × 0.20 × 0.20 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	1678 reflections with I > 2σ(I)
5687 measured reflections	R_int = 0.101
1797 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.064	1 restraint
wR(F²) = 0.173	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.21 e Å⁻³
1797 reflections	Δρ_min = −0.15 e Å⁻³
113 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
C1	0.38120 (16)	0.29404 (19)	0.1522 (5)	0.0521 (6)
C2	0.38140 (19)	0.3629 (2)	0.3552 (6)	0.0627 (7)
H2	0.3252	0.3966	0.4048	0.075*
C3	0.46513 (19)	0.3825 (2)	0.4863 (5)	0.0622 (7)
H3	0.4644	0.4300	0.6224	0.075*
C4	0.54959 (17)	0.33317 (19)	0.4198 (5)	0.0532 (6)
C5	0.54753 (17)	0.2641 (2)	0.2135 (6)	0.0604 (7)
H5	0.6035	0.2298	0.1648	0.072*
C6	0.46503 (18)	0.2445 (2)	0.0779 (6)	0.0577 (6)
H6	0.4658	0.1987	−0.0614	0.069*
C7	0.6424 (2)	0.3537 (2)	0.5558 (5)	0.0639 (7)
H7A	0.6750	0.2860	0.5835	0.077*
H7B	0.6293	0.3854	0.7203	0.077*
C8	0.70702 (18)	0.4287 (2)	0.4049 (5)	0.0573 (6)
H8A	0.7130	0.4007	0.2338	0.069*
H8B	0.6764	0.4984	0.3933	0.069*
C9	0.80525 (18)	0.4441 (2)	0.5120 (5)	0.0622 (7)
C10	0.8711 (2)	0.5121 (3)	0.3595 (8)	0.0852 (11)
H10A	0.9327	0.5135	0.4389	0.128*
H10B	0.8462	0.5839	0.3495	0.128*
H10C	0.8768	0.4828	0.1917	0.128*
O1	0.29729 (13)	0.27805 (18)	0.0238 (5)	0.0713 (6)
H1	0.303 (3)	0.230 (4)	−0.105 (10)	0.107*
O2	0.82901 (17)	0.4040 (2)	0.7093 (5)	0.0906 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0400 (11)	0.0505 (12)	0.0657 (15)	−0.0032 (9)	−0.0021 (10)	0.0083 (11)
C2	0.0480 (12)	0.0688 (15)	0.0715 (16)	0.0096 (11)	0.0080 (11)	0.0007 (13)
C3	0.0634 (15)	0.0657 (14)	0.0576 (13)	0.0022 (12)	0.0011 (12)	−0.0075 (12)
C4	0.0509 (12)	0.0542 (12)	0.0544 (13)	−0.0026 (10)	−0.0061 (10)	0.0062 (10)
C5	0.0419 (11)	0.0611 (13)	0.0782 (17)	0.0042 (10)	−0.0035 (11)	−0.0084 (13)
C6	0.0481 (13)	0.0537 (13)	0.0714 (15)	−0.0009 (10)	−0.0056 (11)	−0.0101 (11)
C7	0.0652 (16)	0.0635 (14)	0.0629 (16)	−0.0026 (13)	−0.0180 (13)	0.0059 (12)
C8	0.0547 (14)	0.0560 (13)	0.0612 (14)	−0.0002 (10)	−0.0136 (11)	−0.0033 (12)
C9	0.0554 (13)	0.0494 (12)	0.0818 (18)	0.0059 (11)	−0.0183 (14)	−0.0129 (13)
C10	0.0637 (18)	0.0765 (19)	0.115 (3)	−0.0186 (14)	−0.0073 (17)	−0.014 (2)
O1	0.0410 (9)	0.0783 (13)	0.0947 (15)	−0.0026 (8)	−0.0109 (10)	−0.0017 (12)
O2	0.0806 (16)	0.0855 (14)	0.1056 (18)	−0.0036 (12)	−0.0449 (14)	0.0113 (14)

Geometric parameters (Å, º) top

C1—C2	1.371 (4)	C7—C8	1.525 (4)
C1—O1	1.372 (3)	C7—H7A	0.9700
C1—C6	1.384 (4)	C7—H7B	0.9700
C2—C3	1.384 (4)	C8—C9	1.501 (3)
C2—H2	0.9300	C8—H8A	0.9700
C3—C4	1.379 (4)	C8—H8B	0.9700
C3—H3	0.9300	C9—O2	1.200 (4)
C4—C5	1.386 (4)	C9—C10	1.489 (5)
C4—C7	1.508 (3)	C10—H10A	0.9600
C5—C6	1.382 (4)	C10—H10B	0.9600
C5—H5	0.9300	C10—H10C	0.9600
C6—H6	0.9300	O1—H1	0.91 (5)

C2—C1—O1	118.5 (2)	C8—C7—H7A	109.3
C2—C1—C6	119.8 (2)	C4—C7—H7B	109.3
O1—C1—C6	121.6 (2)	C8—C7—H7B	109.3
C1—C2—C3	120.1 (2)	H7A—C7—H7B	108.0
C1—C2—H2	120.0	C9—C8—C7	115.3 (2)
C3—C2—H2	120.0	C9—C8—H8A	108.5
C4—C3—C2	121.6 (2)	C7—C8—H8A	108.5
C4—C3—H3	119.2	C9—C8—H8B	108.5
C2—C3—H3	119.2	C7—C8—H8B	108.5
C3—C4—C5	117.2 (2)	H8A—C8—H8B	107.5
C3—C4—C7	123.0 (2)	O2—C9—C10	122.1 (3)
C5—C4—C7	119.7 (2)	O2—C9—C8	121.9 (3)
C6—C5—C4	122.2 (2)	C10—C9—C8	116.0 (3)
C6—C5—H5	118.9	C9—C10—H10A	109.5
C4—C5—H5	118.9	C9—C10—H10B	109.5
C5—C6—C1	119.1 (2)	H10A—C10—H10B	109.5
C5—C6—H6	120.4	C9—C10—H10C	109.5
C1—C6—H6	120.4	H10A—C10—H10C	109.5
C4—C7—C8	111.6 (2)	H10B—C10—H10C	109.5
C4—C7—H7A	109.3	C1—O1—H1	113 (3)

O1—C1—C2—C3	−178.8 (3)	C2—C1—C6—C5	1.2 (4)
C6—C1—C2—C3	−0.3 (4)	O1—C1—C6—C5	179.6 (3)
C1—C2—C3—C4	−0.7 (4)	C3—C4—C7—C8	−102.6 (3)
C2—C3—C4—C5	0.9 (4)	C5—C4—C7—C8	75.6 (3)
C2—C3—C4—C7	179.1 (3)	C4—C7—C8—C9	−173.6 (2)
C3—C4—C5—C6	0.0 (4)	C7—C8—C9—O2	−3.5 (4)
C7—C4—C5—C6	−178.3 (3)	C7—C8—C9—C10	176.7 (2)
C4—C5—C6—C1	−1.0 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱ	0.91 (5)	1.97 (5)	2.842 (4)	161 (5)

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

Experimental details

Crystal data
Chemical formula	C₁₀H₁₂O₂
M_r	164.20
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	298
a, b, c (Å)	14.0242 (13), 12.4450 (12), 5.2706 (5)
V (Å³)	919.88 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.23 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	5687, 1797, 1678
R_int	0.101
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.064, 0.173, 1.06
No. of reflections	1797
No. of parameters	113
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.15

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), 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
O1—H1···O2ⁱ	0.91 (5)	1.97 (5)	2.842 (4)	161 (5)

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

Acknowledgements

The author thanks Professor Xianggao Meng at Hua-Zhong Normal University for the X-ray crystallographic determination and some helpful discussion and theoretical analysis.

References

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