organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

4-(4-Hy­dr­oxy­phen­yl)butan-2-one

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[Larsen, M. & Poll, L. (1990). Z. Lebensm. Unters. Forsch. 191, 129-131.]); Tang (2006[Tang, J. (2006). Technol. Dev. Chem. Ind. 35, 21-23.]). For a related structure, see: Kosjek et al. (2003[Kosjek, B., Stampfer, W., van Deursen, R., Faber, K. & Kroutil, W. (2003). Tetrahedron, 59, 9517-9521.]). For the synthesis, see: Smith (1996[Smith, L. R. (1996). Chem. Educator, 1, 1-18]).

[Scheme 1]

Experimental

Crystal data
  • C10H12O2

  • Mr = 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)

  • Rint = 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

  • Δρmax = 0.21 e Å−3

  • Δρmin = −0.15 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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[Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1997[Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


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.

Refinement top

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 Uiso(H)=1.2Ueq(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 Uiso(H)=1.5Ueq(O).

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
[Figure 1] Fig. 1. View of the molecule of (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] 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
C10H12O2F(000) = 352
Mr = 164.20Dx = 1.186 Mg m3
Orthorhombic, Pna21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 2580 reflections
a = 14.0242 (13) Åθ = 2.2–24.5°
b = 12.4450 (12) ŵ = 0.08 mm1
c = 5.2706 (5) ÅT = 298 K
V = 919.88 (15) Å3Block, colourless
Z = 40.23 × 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 tubeRint = 0.101
Graphite monochromatorθmax = 26.0°, θmin = 2.2°
ϕ and ω scansh = 1617
5687 measured reflectionsk = 1215
1797 independent reflectionsl = 66
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.064Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.173H 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 parametersΔρmax = 0.21 e Å3
1 restraintΔρmin = 0.15 e Å3
Crystal data top
C10H12O2V = 919.88 (15) Å3
Mr = 164.20Z = 4
Orthorhombic, Pna21Mo Kα radiation
a = 14.0242 (13) ŵ = 0.08 mm1
b = 12.4450 (12) ÅT = 298 K
c = 5.2706 (5) Å0.23 × 0.20 × 0.20 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
1678 reflections with I > 2σ(I)
5687 measured reflectionsRint = 0.101
1797 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0641 restraint
wR(F2) = 0.173H atoms treated by a mixture of independent and constrained refinement
S = 1.06Δρmax = 0.21 e Å3
1797 reflectionsΔρmin = 0.15 e Å3
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
xyzUiso*/Ueq
C10.38120 (16)0.29404 (19)0.1522 (5)0.0521 (6)
C20.38140 (19)0.3629 (2)0.3552 (6)0.0627 (7)
H20.32520.39660.40480.075*
C30.46513 (19)0.3825 (2)0.4863 (5)0.0622 (7)
H30.46440.43000.62240.075*
C40.54959 (17)0.33317 (19)0.4198 (5)0.0532 (6)
C50.54753 (17)0.2641 (2)0.2135 (6)0.0604 (7)
H50.60350.22980.16480.072*
C60.46503 (18)0.2445 (2)0.0779 (6)0.0577 (6)
H60.46580.19870.06140.069*
C70.6424 (2)0.3537 (2)0.5558 (5)0.0639 (7)
H7A0.67500.28600.58350.077*
H7B0.62930.38540.72030.077*
C80.70702 (18)0.4287 (2)0.4049 (5)0.0573 (6)
H8A0.71300.40070.23380.069*
H8B0.67640.49840.39330.069*
C90.80525 (18)0.4441 (2)0.5120 (5)0.0622 (7)
C100.8711 (2)0.5121 (3)0.3595 (8)0.0852 (11)
H10A0.93270.51350.43890.128*
H10B0.84620.58390.34950.128*
H10C0.87680.48280.19170.128*
O10.29729 (13)0.27805 (18)0.0238 (5)0.0713 (6)
H10.303 (3)0.230 (4)0.105 (10)0.107*
O20.82901 (17)0.4040 (2)0.7093 (5)0.0906 (8)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0400 (11)0.0505 (12)0.0657 (15)0.0032 (9)0.0021 (10)0.0083 (11)
C20.0480 (12)0.0688 (15)0.0715 (16)0.0096 (11)0.0080 (11)0.0007 (13)
C30.0634 (15)0.0657 (14)0.0576 (13)0.0022 (12)0.0011 (12)0.0075 (12)
C40.0509 (12)0.0542 (12)0.0544 (13)0.0026 (10)0.0061 (10)0.0062 (10)
C50.0419 (11)0.0611 (13)0.0782 (17)0.0042 (10)0.0035 (11)0.0084 (13)
C60.0481 (13)0.0537 (13)0.0714 (15)0.0009 (10)0.0056 (11)0.0101 (11)
C70.0652 (16)0.0635 (14)0.0629 (16)0.0026 (13)0.0180 (13)0.0059 (12)
C80.0547 (14)0.0560 (13)0.0612 (14)0.0002 (10)0.0136 (11)0.0033 (12)
C90.0554 (13)0.0494 (12)0.0818 (18)0.0059 (11)0.0183 (14)0.0129 (13)
C100.0637 (18)0.0765 (19)0.115 (3)0.0186 (14)0.0073 (17)0.014 (2)
O10.0410 (9)0.0783 (13)0.0947 (15)0.0026 (8)0.0109 (10)0.0017 (12)
O20.0806 (16)0.0855 (14)0.1056 (18)0.0036 (12)0.0449 (14)0.0113 (14)
Geometric parameters (Å, º) top
C1—C21.371 (4)C7—C81.525 (4)
C1—O11.372 (3)C7—H7A0.9700
C1—C61.384 (4)C7—H7B0.9700
C2—C31.384 (4)C8—C91.501 (3)
C2—H20.9300C8—H8A0.9700
C3—C41.379 (4)C8—H8B0.9700
C3—H30.9300C9—O21.200 (4)
C4—C51.386 (4)C9—C101.489 (5)
C4—C71.508 (3)C10—H10A0.9600
C5—C61.382 (4)C10—H10B0.9600
C5—H50.9300C10—H10C0.9600
C6—H60.9300O1—H10.91 (5)
C2—C1—O1118.5 (2)C8—C7—H7A109.3
C2—C1—C6119.8 (2)C4—C7—H7B109.3
O1—C1—C6121.6 (2)C8—C7—H7B109.3
C1—C2—C3120.1 (2)H7A—C7—H7B108.0
C1—C2—H2120.0C9—C8—C7115.3 (2)
C3—C2—H2120.0C9—C8—H8A108.5
C4—C3—C2121.6 (2)C7—C8—H8A108.5
C4—C3—H3119.2C9—C8—H8B108.5
C2—C3—H3119.2C7—C8—H8B108.5
C3—C4—C5117.2 (2)H8A—C8—H8B107.5
C3—C4—C7123.0 (2)O2—C9—C10122.1 (3)
C5—C4—C7119.7 (2)O2—C9—C8121.9 (3)
C6—C5—C4122.2 (2)C10—C9—C8116.0 (3)
C6—C5—H5118.9C9—C10—H10A109.5
C4—C5—H5118.9C9—C10—H10B109.5
C5—C6—C1119.1 (2)H10A—C10—H10B109.5
C5—C6—H6120.4C9—C10—H10C109.5
C1—C6—H6120.4H10A—C10—H10C109.5
C4—C7—C8111.6 (2)H10B—C10—H10C109.5
C4—C7—H7A109.3C1—O1—H1113 (3)
O1—C1—C2—C3178.8 (3)C2—C1—C6—C51.2 (4)
C6—C1—C2—C30.3 (4)O1—C1—C6—C5179.6 (3)
C1—C2—C3—C40.7 (4)C3—C4—C7—C8102.6 (3)
C2—C3—C4—C50.9 (4)C5—C4—C7—C875.6 (3)
C2—C3—C4—C7179.1 (3)C4—C7—C8—C9173.6 (2)
C3—C4—C5—C60.0 (4)C7—C8—C9—O23.5 (4)
C7—C4—C5—C6178.3 (3)C7—C8—C9—C10176.7 (2)
C4—C5—C6—C11.0 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O2i0.91 (5)1.97 (5)2.842 (4)161 (5)
Symmetry code: (i) x1/2, y+1/2, z1.

Experimental details

Crystal data
Chemical formulaC10H12O2
Mr164.20
Crystal system, space groupOrthorhombic, Pna21
Temperature (K)298
a, b, c (Å)14.0242 (13), 12.4450 (12), 5.2706 (5)
V3)919.88 (15)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.23 × 0.20 × 0.20
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
5687, 1797, 1678
Rint0.101
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.064, 0.173, 1.06
No. of reflections1797
No. of parameters113
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
O1—H1···O2i0.91 (5)1.97 (5)2.842 (4)161 (5)
Symmetry code: (i) x1/2, y+1/2, z1.
 

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

First citationBruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationKosjek, B., Stampfer, W., van Deursen, R., Faber, K. & Kroutil, W. (2003). Tetrahedron, 59, 9517–9521.  CrossRef CAS Google Scholar
First citationLarsen, M. & Poll, L. (1990). Z. Lebensm. Unters. Forsch. 191, 129–131.  CrossRef CAS Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSmith, L. R. (1996). Chem. Educator, 1, 1–18  Google Scholar
First citationTang, J. (2006). Technol. Dev. Chem. Ind. 35, 21–23.  CAS Google Scholar

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