4-(4-Hy­droxy­phen­yl)butan-2-one

Abstract

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,

• a = 14.0242 (13) Å

• b = 12.4450 (12) Å

• c = 5.2706 (5) Å

• V = 919.88 (15) ų

• 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[F ² > 2σ(F ²)] = 0.064

• wR(F ²) = 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

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.

Supplementary Material

Supplementary material file. DOI: 10.1107/S1600536811017272/sj5132Isup3.cml

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

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) .

supplementary crystallographic information

Comment

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).

Experimental

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.

Refinement

All the carbon-bounded hydrogen atoms were located at their ideal positions with the C—H=0.93 Å,C—H=0.96 Å, C—H=0.97 Å, and U_iso(H)=1.2U_eq(C). The hydrogen atom bonded to the oxygen atom was located from the difference map and refined with the restraints of O—H = 0.91 (5)Å and U_iso(H)=1.5U_eq(O).

Figures

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.

Crystal data

C10H12O2	F(000) = 352
Mr = 164.20	Dx = 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

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

Refinement

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(Fo2) + (0.1055P)2 + 0.082P] where P = (Fo2 + 2Fc2)/3
1797 reflections	(Δ/σ)max < 0.001
113 parameters	Δρmax = 0.21 e Å−3
1 restraint	Δρmin = −0.15 e Å−3

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 (Ų)

	x	y	z	Uiso*/Ueq
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 (Ų)

	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, °)

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, °)

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 codes: (i) x−1/2, −y+1/2, z−1.