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Acta Crystallogr Sect E Struct Rep Online. 2008 August 1; 64(Pt 8): o1465.
Published online 2008 July 12. doi:  10.1107/S1600536808020886
PMCID: PMC2962095

4-Hydr­oxy-4,4-diphenyl­butan-2-one

Abstract

The mol­ecules of the title compound, C16H16O2, display an intra­molecular O—H(...)O hydrogen bond between the hydroxyl donor and the ketone acceptor. Inter­molecular C—H(...)π inter­actions connect adjacent mol­ecules into chains that propagate parallel to the ac diagonal. The chains are arranged in sheets, and mol­ecules in adjacent sheets inter­act via inter­molecular O—H(...)O hydrogen bonds.

Related literature

For related literature, see: Rivett (1980 [triangle]); Paulson et al. (1973 [triangle]).

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Object name is e-64-o1465-scheme1.jpg

Experimental

Crystal data

  • C16H16O2
  • M r = 240.29
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1465-efi1.jpg
  • a = 9.8619 (2) Å
  • b = 9.2015 (2) Å
  • c = 14.3720 (3) Å
  • β = 102.098 (2)°
  • V = 1275.21 (5) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 150 (2) K
  • 0.35 × 0.30 × 0.20 mm

Data collection

  • Oxford Diffraction Gemini diffractometer
  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 [triangle]) T min = 0.933, T max = 0.984
  • 7361 measured reflections
  • 2935 independent reflections
  • 2144 reflections with I > 2σ(I)
  • R int = 0.021

Refinement

  • R[F 2 > 2σ(F 2)] = 0.036
  • wR(F 2) = 0.066
  • S = 1.01
  • 2935 reflections
  • 167 parameters
  • 1 restraint
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.22 e Å−3
  • Δρmin = −0.20 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2007 [triangle]); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 [triangle]); data reduction: CrysAlis RED; program(s) used to solve structure: SIR97 (Altomare et al. 1999 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 (Farrugia, 1997 [triangle]) and CrystalMaker (CrystalMaker, 2006 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2008 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808020886/hg2422sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808020886/hg2422Isup2.hkl

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

Acknowledgments

The authors gratefully acknowledge the Synthesis and Molecular Recognition Program, Faculty of Science, Queensland University of Technology, for financial support.

supplementary crystallographic information

Comment

The molecular stucture of the title compound, (I), is illustrated in Fig. 1. There is an intramolecular hydrogen bond between the hydroxyl moiety and the ketone oxygen. The molecules are arranged in chains that propagate parallel to the ac diagonal via intermolecular CH···π interactions. There are two such interactions; the aromatic ring comprising C5—C10 is the CH donor and the ring comprising C11—C16 is the acceptor in both cases. Geometric parameters for the two interactions are as follows; C6—H6···C11—C16plane distance 2.731 Å with C5—C10plane···C11—C16plane dihedral angle 78.67° and C8—H8···C11—C16plane distance 2.947 Å with C5—C10plane···C11—C16plane dihedral angle 83.52°. The chains stack to form two-dimensional sheets in the crystal structure (Fig. 2). Intermolecular hydrogen bonds connect pairs of molecules from contiguous two-dimensional sheets. The pairwise intermolecular H-bond interactions and the intramolecular H-bond interactions are illustrated in Fig. 3.

Experimental

The title compound was prepared according to the procedure described by Rivett (1980) which is an adaptation of the method reported earlier by Paulson et al. (1973). Large colourless prismatic crystals of the compound were obtained by crystallization from an evaporating dichloromethane/methanol solution.

Refinement

C-bound H atoms were included in idealized positions and refined using a riding model approximation with methylene, methyl and aromatic bond lengths fixed at 0.99, 0.98 and 0.95 Å, respectively. Uiso(H) values were fixed at 1.2Ueq of the parent C atoms for methylene and aromatic H atoms and 1.5Ueq of the parent C atoms for methyl H atoms. The hydroxy H atom was located in a Fourier difference map and refined with an O—H bond length restraint of 0.98 Å and with Uiso fixed at 1.5Ueq of the parent O atom.

Figures

Fig. 1.
ORTEP depiction of the molecular structure with atom numbering scheme. Ellipsoids are drawn at the 50% probability level.
Fig. 2.
(a) The molecules are arranged in sheets. Within the sheets the molecules are linked in one-dimensional chains by CH···π interactions between phenyl rings. Once such chain is highlighted with alternating molecules coloured ...
Fig. 3.
Molecules in adjacent two-dimensional sheets are connected by intermolecular hydrogen bonds. The arrangement of these hydrogen bonds between a pair of molecules is illustrated (red/white dashed contact). The intramolecular hydrogen bonds are also shown ...

Crystal data

C16H16O2F000 = 512
Mr = 240.29Dx = 1.252 Mg m3
Monoclinic, P21/nMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 3618 reflections
a = 9.8619 (2) Åθ = 2.9–28.7º
b = 9.2015 (2) ŵ = 0.08 mm1
c = 14.3720 (3) ÅT = 150 (2) K
β = 102.098 (2)ºPrism, colourless
V = 1275.21 (5) Å30.35 × 0.30 × 0.20 mm
Z = 4

Data collection

Oxford Diffraction Gemini diffractometer2935 independent reflections
Radiation source: Enhance (Mo) X-ray Source2144 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.021
Detector resolution: 16.0774 pixels mm-1θmax = 28.8º
T = 150(2) Kθmin = 2.9º
ω scansh = −11→12
Absorption correction: multi-scan(CrysAlis RED; Oxford Diffraction, 2007)k = −12→12
Tmin = 0.933, Tmax = 0.984l = −19→19
7361 measured reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.066  w = 1/[σ2(Fo2) + (0.01P)2 + 0.4P] where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.001
2935 reflectionsΔρmax = 0.22 e Å3
167 parametersΔρmin = −0.20 e Å3
1 restraintExtinction correction: none
Primary atom site location: structure-invariant direct methods

Special details

Experimental. Crystal cleaved from larger prism.Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.
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)

xyzUiso*/Ueq
C10.55546 (14)0.14657 (15)0.76771 (9)0.0373 (3)
H1A0.60470.05380.76940.056*
H1B0.62240.22660.77500.056*
H1C0.48960.15620.70670.056*
C20.47849 (12)0.15136 (14)0.84736 (8)0.0276 (3)
C30.42255 (12)0.29752 (13)0.86860 (8)0.0256 (3)
H3A0.38020.34490.80760.031*
H3B0.50120.35890.90040.031*
C40.31411 (11)0.29285 (13)0.93164 (7)0.0224 (2)
C50.27448 (11)0.44508 (13)0.95954 (8)0.0227 (2)
C60.30596 (13)0.57091 (14)0.91585 (8)0.0294 (3)
H60.35610.56480.86630.035*
C70.26527 (13)0.70651 (14)0.94343 (9)0.0328 (3)
H70.28750.79200.91270.039*
C80.19261 (12)0.71662 (14)1.01542 (8)0.0311 (3)
H80.16490.80891.03450.037*
C90.16028 (13)0.59169 (15)1.05965 (9)0.0330 (3)
H90.11000.59831.10910.040*
C100.20081 (13)0.45708 (14)1.03224 (8)0.0291 (3)
H100.17830.37191.06320.035*
C110.18229 (11)0.21520 (13)0.87881 (7)0.0221 (2)
C120.10703 (12)0.27142 (14)0.79318 (8)0.0282 (3)
H120.13790.35760.76770.034*
C13−0.01221 (13)0.20283 (15)0.74497 (8)0.0336 (3)
H13−0.06270.24230.68690.040*
C14−0.05786 (13)0.07704 (15)0.78118 (9)0.0344 (3)
H14−0.13900.02940.74770.041*
C150.01500 (13)0.02096 (15)0.86617 (9)0.0341 (3)
H15−0.0165−0.06500.89150.041*
C160.13418 (12)0.08994 (14)0.91473 (8)0.0281 (3)
H160.18340.05080.97330.034*
O10.46398 (10)0.04232 (10)0.89213 (6)0.0388 (2)
O20.37110 (8)0.22230 (9)1.01953 (5)0.02635 (19)
H2O0.4104 (14)0.1379 (14)1.0054 (9)0.040*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0371 (8)0.0363 (8)0.0426 (7)0.0045 (6)0.0178 (6)−0.0073 (6)
C20.0246 (6)0.0290 (7)0.0283 (6)0.0047 (5)0.0030 (5)−0.0038 (5)
C30.0260 (6)0.0247 (6)0.0271 (6)0.0035 (5)0.0077 (5)−0.0001 (5)
C40.0258 (6)0.0221 (6)0.0196 (5)0.0044 (5)0.0057 (4)0.0023 (5)
C50.0219 (6)0.0225 (6)0.0230 (5)0.0026 (5)0.0032 (4)−0.0014 (5)
C60.0337 (7)0.0256 (7)0.0315 (6)0.0036 (5)0.0127 (5)0.0010 (6)
C70.0379 (7)0.0221 (6)0.0391 (7)0.0039 (6)0.0099 (6)0.0023 (6)
C80.0316 (7)0.0245 (7)0.0360 (6)0.0080 (6)0.0042 (5)−0.0057 (6)
C90.0348 (7)0.0341 (7)0.0331 (6)0.0062 (6)0.0141 (5)−0.0043 (6)
C100.0336 (7)0.0259 (7)0.0304 (6)0.0016 (5)0.0126 (5)0.0008 (5)
C110.0247 (6)0.0227 (6)0.0200 (5)0.0055 (5)0.0074 (4)−0.0024 (5)
C120.0318 (6)0.0310 (7)0.0227 (6)0.0070 (6)0.0078 (5)0.0012 (5)
C130.0318 (7)0.0444 (8)0.0230 (6)0.0105 (6)0.0018 (5)−0.0046 (6)
C140.0257 (6)0.0414 (8)0.0354 (7)0.0009 (6)0.0049 (5)−0.0143 (6)
C150.0333 (7)0.0308 (7)0.0396 (7)−0.0031 (6)0.0110 (6)−0.0035 (6)
C160.0307 (7)0.0270 (7)0.0268 (6)0.0027 (5)0.0063 (5)0.0007 (5)
O10.0515 (6)0.0275 (5)0.0405 (5)0.0123 (4)0.0166 (4)0.0030 (4)
O20.0320 (5)0.0241 (5)0.0214 (4)0.0077 (4)0.0021 (3)0.0016 (4)

Geometric parameters (Å, °)

C1—C21.5009 (16)C8—C91.3828 (18)
C1—H1A0.9800C8—H80.9500
C1—H1B0.9800C9—C101.3839 (17)
C1—H1C0.9800C9—H90.9500
C2—O11.2165 (15)C10—H100.9500
C2—C31.5089 (16)C11—C161.3866 (16)
C3—C41.5403 (15)C11—C121.3965 (15)
C3—H3A0.9900C12—C131.3855 (17)
C3—H3B0.9900C12—H120.9500
C4—O21.4266 (13)C13—C141.3826 (19)
C4—C51.5301 (16)C13—H130.9500
C4—C111.5373 (16)C14—C151.3808 (18)
C5—C61.3830 (16)C14—H140.9500
C5—C101.3964 (15)C15—C161.3884 (17)
C6—C71.3934 (17)C15—H150.9500
C6—H60.9500C16—H160.9500
C7—C81.3795 (17)O2—H2O0.910 (12)
C7—H70.9500
C2—C1—H1A109.5C6—C7—H7120.0
C2—C1—H1B109.5C7—C8—C9119.65 (12)
H1A—C1—H1B109.5C7—C8—H8120.2
C2—C1—H1C109.5C9—C8—H8120.2
H1A—C1—H1C109.5C8—C9—C10120.33 (11)
H1B—C1—H1C109.5C8—C9—H9119.8
O1—C2—C1120.90 (12)C10—C9—H9119.8
O1—C2—C3122.65 (11)C9—C10—C5120.69 (12)
C1—C2—C3116.44 (11)C9—C10—H10119.7
C2—C3—C4114.99 (10)C5—C10—H10119.7
C2—C3—H3A108.5C16—C11—C12118.42 (11)
C4—C3—H3A108.5C16—C11—C4121.49 (10)
C2—C3—H3B108.5C12—C11—C4120.09 (11)
C4—C3—H3B108.5C13—C12—C11120.70 (12)
H3A—C3—H3B107.5C13—C12—H12119.6
O2—C4—C5105.04 (8)C11—C12—H12119.6
O2—C4—C11111.18 (9)C14—C13—C12120.15 (11)
C5—C4—C11108.60 (9)C14—C13—H13119.9
O2—C4—C3109.89 (9)C12—C13—H13119.9
C5—C4—C3112.06 (10)C15—C14—C13119.72 (12)
C11—C4—C3110.00 (9)C15—C14—H14120.1
C6—C5—C10118.35 (11)C13—C14—H14120.1
C6—C5—C4123.61 (10)C14—C15—C16120.17 (12)
C10—C5—C4118.03 (10)C14—C15—H15119.9
C5—C6—C7121.00 (11)C16—C15—H15119.9
C5—C6—H6119.5C11—C16—C15120.84 (11)
C7—C6—H6119.5C11—C16—H16119.6
C8—C7—C6119.97 (12)C15—C16—H16119.6
C8—C7—H7120.0C4—O2—H2O107.4 (8)
O1—C2—C3—C4−15.52 (17)C6—C5—C10—C90.08 (18)
C1—C2—C3—C4165.07 (10)C4—C5—C10—C9−179.04 (11)
C2—C3—C4—O257.09 (13)O2—C4—C11—C16−2.22 (14)
C2—C3—C4—C5173.47 (9)C5—C4—C11—C16−117.30 (11)
C2—C3—C4—C11−65.63 (12)C3—C4—C11—C16119.73 (11)
O2—C4—C5—C6133.63 (11)O2—C4—C11—C12177.02 (10)
C11—C4—C5—C6−107.35 (12)C5—C4—C11—C1261.94 (13)
C3—C4—C5—C614.36 (15)C3—C4—C11—C12−61.03 (13)
O2—C4—C5—C10−47.29 (13)C16—C11—C12—C13−0.53 (17)
C11—C4—C5—C1071.72 (12)C4—C11—C12—C13−179.79 (11)
C3—C4—C5—C10−166.56 (10)C11—C12—C13—C14−0.24 (18)
C10—C5—C6—C7−0.05 (18)C12—C13—C14—C150.74 (18)
C4—C5—C6—C7179.02 (11)C13—C14—C15—C16−0.48 (19)
C5—C6—C7—C80.10 (19)C12—C11—C16—C150.79 (17)
C6—C7—C8—C9−0.17 (19)C4—C11—C16—C15−179.96 (11)
C7—C8—C9—C100.21 (19)C14—C15—C16—C11−0.29 (18)
C8—C9—C10—C5−0.16 (19)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O2—H2O···O10.910 (12)2.016 (12)2.7636 (12)138.5 (11)
O2—H2O···O1i0.910 (12)2.385 (13)3.0530 (12)130.3 (10)

Symmetry codes: (i) −x+1, −y, −z+2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG2422).

References

  • Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst.32, 115–119.
  • CrystalMaker (2006). CrystalMaker CrystalMaker Software, Yarnton, Oxfordshire, UK.
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.
  • Paulson, D. R., Hartwig, A. L. & Moran, G. F. (1973). J. Chem. Educ.50, 216–217.
  • Rivett, E. E. A. (1980). J. Chem. Educ.57, 751.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2008). publCIF. In preparation.

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