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Acta Crystallogr Sect E Struct Rep Online. 2009 July 1; 65(Pt 7): o1717.
Published online 2009 June 27. doi:  10.1107/S1600536809024027
PMCID: PMC2969281

4-(4-Pentyl­cyclo­hexyl)phenol

Abstract

In the title compound, C17H26O, the cyclo­hexyl ring adopts a chair conformation with the C-atom substituents in equatorial sites. The H atom of the O—H group is disordered over two positions of equal occupancy. In the crystal, O—H(...)O hydrogen bonds lead to [010] chains.

Related literature

For a related structure, see: Wang et al. (2006 [triangle]). For applications of phenol derivatives, see: Eidenschink et al. (1978 [triangle]); Hu et al. (2003 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o1717-scheme1.jpg

Experimental

Crystal data

  • C17H26O
  • M r = 246.38
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1717-efi1.jpg
  • a = 21.002 (4) Å
  • b = 5.3281 (11) Å
  • c = 13.389 (3) Å
  • β = 105.87 (3)°
  • V = 1441.2 (5) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.07 mm−1
  • T = 113 K
  • 0.24 × 0.20 × 0.10 mm

Data collection

  • Rigaku Saturn CCD diffractometer
  • Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 [triangle]) T min = 0.984, T max = 0.993
  • 10687 measured reflections
  • 2827 independent reflections
  • 2314 reflections with I > 2σ(I)
  • R int = 0.040

Refinement

  • R[F 2 > 2σ(F 2)] = 0.056
  • wR(F 2) = 0.151
  • S = 1.11
  • 2827 reflections
  • 170 parameters
  • 2 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.19 e Å−3
  • Δρmin = −0.25 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 [triangle]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809024027/hb5011sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809024027/hb5011Isup2.hkl

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

supplementary crystallographic information

Comment

For a related structure, see Wang et al. (2006); for uses of phenol derivatives, see Eidenschink et al., 1978; Hu et al., 2003). In the title compound, (I), the H atom of O—H bond was found disordered in two orientation. The crystal structure is stabilized by O—H···O hydrogen bonds (Table 1).

Refinement

The H atoms of O—H were located in a difference map and their positions were freely refined. All H other atoms were positioned geometrically and refined using a riding model, in the range of 0.93–0.98 Å, with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C).

Figures

Fig. 1.
The molecular structure of (I). Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radius. Only one orientation of the O—H group is shown.

Crystal data

C17H26OF(000) = 544
Mr = 246.38Dx = 1.136 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3895 reflections
a = 21.002 (4) Åθ = 1.6–27.9°
b = 5.3281 (11) ŵ = 0.07 mm1
c = 13.389 (3) ÅT = 113 K
β = 105.87 (3)°Block, colourless
V = 1441.2 (5) Å30.24 × 0.20 × 0.10 mm
Z = 4

Data collection

Rigaku Saturn CCD diffractometer2827 independent reflections
Radiation source: rotating anode2314 reflections with I > 2σ(I)
confocalRint = 0.040
Detector resolution: 7.31 pixels mm-1θmax = 26.0°, θmin = 2.0°
ω and [var phi] scansh = −25→22
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)k = −6→6
Tmin = 0.984, Tmax = 0.993l = −16→15
10687 measured reflections

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.151H atoms treated by a mixture of independent and constrained refinement
S = 1.11w = 1/[σ2(Fo2) + (0.0738P)2 + 0.2552P] where P = (Fo2 + 2Fc2)/3
2827 reflections(Δ/σ)max = 0.001
170 parametersΔρmax = 0.19 e Å3
2 restraintsΔρmin = −0.25 e Å3

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 (Å2)

xyzUiso*/UeqOcc. (<1)
O10.48580 (6)0.2525 (2)0.02646 (9)0.0245 (3)
H1A0.4889 (19)0.399 (5)−0.001 (3)0.037*0.50
H1B0.4982 (19)0.107 (5)0.018 (3)0.037*0.50
C10.41419 (7)0.0832 (3)0.23796 (11)0.0186 (3)
H10.4178−0.04660.28780.022*
C20.45317 (7)0.0725 (3)0.16908 (11)0.0195 (3)
H20.4833−0.06210.17230.023*
C30.44742 (7)0.2600 (3)0.09596 (11)0.0189 (3)
C40.40401 (7)0.4582 (3)0.09173 (11)0.0199 (4)
H40.40060.58760.04170.024*
C50.36564 (7)0.4663 (3)0.16100 (11)0.0197 (4)
H50.33570.60180.15760.024*
C60.36995 (7)0.2801 (3)0.23555 (11)0.0180 (3)
C70.32602 (7)0.2816 (3)0.30842 (11)0.0183 (4)
H70.34290.14910.36210.022*
C80.32710 (7)0.5321 (3)0.36579 (11)0.0205 (4)
H8A0.37290.56790.40740.025*
H8B0.31320.66850.31420.025*
C90.28151 (7)0.5298 (3)0.43741 (11)0.0211 (4)
H9A0.28200.69770.46940.025*
H9B0.29850.40700.49390.025*
C100.20997 (7)0.4612 (3)0.37901 (11)0.0196 (4)
H100.19290.59330.32530.024*
C110.20944 (8)0.2107 (3)0.32292 (12)0.0215 (4)
H11A0.22400.07590.37510.026*
H11B0.16360.17220.28200.026*
C120.25437 (7)0.2132 (3)0.25071 (12)0.0208 (4)
H12A0.23720.33620.19440.025*
H12B0.25360.04550.21860.025*
C130.16400 (8)0.4506 (3)0.44966 (12)0.0227 (4)
H13A0.12140.37580.41010.027*
H13B0.18380.33690.50840.027*
C140.14968 (8)0.7019 (3)0.49357 (12)0.0238 (4)
H14A0.19170.77370.53660.029*
H14B0.13150.81910.43540.029*
C150.10106 (8)0.6811 (3)0.55919 (12)0.0258 (4)
H15A0.05960.60380.51670.031*
H15B0.12000.56760.61840.031*
C160.08453 (8)0.9309 (3)0.60091 (13)0.0273 (4)
H16A0.12621.01500.63860.033*
H16B0.06211.03950.54170.033*
C170.04046 (9)0.9051 (4)0.67340 (14)0.0402 (5)
H17A−0.00060.81940.63710.060*
H17B0.03011.07210.69530.060*
H17C0.06350.80710.73450.060*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0299 (7)0.0234 (6)0.0256 (7)0.0001 (5)0.0169 (5)−0.0007 (5)
C10.0216 (8)0.0165 (7)0.0183 (8)−0.0007 (6)0.0064 (6)0.0006 (6)
C20.0201 (7)0.0172 (7)0.0217 (8)0.0017 (6)0.0065 (6)−0.0008 (6)
C30.0194 (8)0.0214 (8)0.0168 (8)−0.0025 (6)0.0066 (6)−0.0024 (6)
C40.0239 (8)0.0181 (7)0.0172 (8)−0.0014 (6)0.0051 (6)0.0009 (6)
C50.0223 (8)0.0174 (7)0.0196 (8)0.0027 (6)0.0059 (6)−0.0005 (6)
C60.0194 (8)0.0189 (8)0.0152 (8)−0.0010 (6)0.0038 (6)−0.0020 (6)
C70.0204 (8)0.0183 (8)0.0170 (8)0.0013 (6)0.0063 (6)0.0015 (6)
C80.0206 (8)0.0209 (8)0.0205 (8)−0.0013 (6)0.0066 (6)−0.0026 (6)
C90.0226 (8)0.0220 (8)0.0200 (8)0.0013 (6)0.0083 (7)−0.0022 (6)
C100.0223 (8)0.0192 (8)0.0183 (8)0.0000 (6)0.0074 (6)0.0010 (6)
C110.0222 (8)0.0217 (8)0.0218 (8)−0.0030 (6)0.0081 (7)−0.0015 (6)
C120.0237 (8)0.0189 (8)0.0210 (8)−0.0009 (6)0.0079 (7)−0.0017 (6)
C130.0246 (8)0.0229 (8)0.0230 (8)−0.0007 (6)0.0105 (7)0.0006 (6)
C140.0248 (8)0.0254 (9)0.0240 (9)−0.0008 (6)0.0112 (7)−0.0006 (6)
C150.0282 (9)0.0278 (9)0.0249 (9)0.0001 (7)0.0134 (7)0.0007 (7)
C160.0257 (9)0.0326 (10)0.0260 (9)−0.0005 (7)0.0112 (7)−0.0052 (7)
C170.0337 (10)0.0584 (13)0.0346 (11)−0.0006 (9)0.0193 (9)−0.0108 (9)

Geometric parameters (Å, °)

O1—C31.3883 (17)C10—C131.5264 (19)
O1—H1A0.87 (2)C10—C111.530 (2)
O1—H1B0.84 (2)C10—H101.0000
C1—C21.3918 (19)C11—C121.5245 (19)
C1—C61.396 (2)C11—H11A0.9900
C1—H10.9500C11—H11B0.9900
C2—C31.381 (2)C12—H12A0.9900
C2—H20.9500C12—H12B0.9900
C3—C41.386 (2)C13—C141.525 (2)
C4—C51.3856 (19)C13—H13A0.9900
C4—H40.9500C13—H13B0.9900
C5—C61.393 (2)C14—C151.5222 (19)
C5—H50.9500C14—H14A0.9900
C6—C71.5151 (19)C14—H14B0.9900
C7—C121.536 (2)C15—C161.520 (2)
C7—C81.5373 (19)C15—H15A0.9900
C7—H71.0000C15—H15B0.9900
C8—C91.5291 (19)C16—C171.520 (2)
C8—H8A0.9900C16—H16A0.9900
C8—H8B0.9900C16—H16B0.9900
C9—C101.536 (2)C17—H17A0.9800
C9—H9A0.9900C17—H17B0.9800
C9—H9B0.9900C17—H17C0.9800
C3—O1—H1A112 (3)C9—C10—H10107.9
C3—O1—H1B112 (3)C12—C11—C10112.39 (12)
H1A—O1—H1B135 (4)C12—C11—H11A109.1
C2—C1—C6121.60 (13)C10—C11—H11A109.1
C2—C1—H1119.2C12—C11—H11B109.1
C6—C1—H1119.2C10—C11—H11B109.1
C3—C2—C1119.14 (13)H11A—C11—H11B107.9
C3—C2—H2120.4C11—C12—C7111.98 (12)
C1—C2—H2120.4C11—C12—H12A109.2
C2—C3—C4120.62 (14)C7—C12—H12A109.2
C2—C3—O1120.02 (13)C11—C12—H12B109.2
C4—C3—O1119.36 (13)C7—C12—H12B109.2
C5—C4—C3119.51 (13)H12A—C12—H12B107.9
C5—C4—H4120.2C14—C13—C10115.56 (12)
C3—C4—H4120.2C14—C13—H13A108.4
C4—C5—C6121.46 (13)C10—C13—H13A108.4
C4—C5—H5119.3C14—C13—H13B108.4
C6—C5—H5119.3C10—C13—H13B108.4
C5—C6—C1117.67 (13)H13A—C13—H13B107.5
C5—C6—C7121.73 (13)C15—C14—C13113.12 (13)
C1—C6—C7120.52 (13)C15—C14—H14A109.0
C6—C7—C12111.11 (11)C13—C14—H14A109.0
C6—C7—C8113.45 (12)C15—C14—H14B109.0
C12—C7—C8109.63 (12)C13—C14—H14B109.0
C6—C7—H7107.5H14A—C14—H14B107.8
C12—C7—H7107.5C16—C15—C14113.88 (13)
C8—C7—H7107.5C16—C15—H15A108.8
C9—C8—C7112.35 (12)C14—C15—H15A108.8
C9—C8—H8A109.1C16—C15—H15B108.8
C7—C8—H8A109.1C14—C15—H15B108.8
C9—C8—H8B109.1H15A—C15—H15B107.7
C7—C8—H8B109.1C17—C16—C15113.29 (14)
H8A—C8—H8B107.9C17—C16—H16A108.9
C8—C9—C10112.06 (12)C15—C16—H16A108.9
C8—C9—H9A109.2C17—C16—H16B108.9
C10—C9—H9A109.2C15—C16—H16B108.9
C8—C9—H9B109.2H16A—C16—H16B107.7
C10—C9—H9B109.2C16—C17—H17A109.5
H9A—C9—H9B107.9C16—C17—H17B109.5
C13—C10—C11110.54 (12)H17A—C17—H17B109.5
C13—C10—C9112.94 (12)C16—C17—H17C109.5
C11—C10—C9109.41 (12)H17A—C17—H17C109.5
C13—C10—H10107.9H17B—C17—H17C109.5
C11—C10—H10107.9
C6—C1—C2—C3−0.6 (2)C12—C7—C8—C954.21 (15)
C1—C2—C3—C40.8 (2)C7—C8—C9—C10−55.74 (16)
C1—C2—C3—O1−179.92 (12)C8—C9—C10—C13178.39 (12)
C2—C3—C4—C5−0.7 (2)C8—C9—C10—C1154.80 (16)
O1—C3—C4—C5−179.99 (12)C13—C10—C11—C12179.57 (12)
C3—C4—C5—C60.4 (2)C9—C10—C11—C12−55.45 (16)
C4—C5—C6—C1−0.3 (2)C10—C11—C12—C756.67 (16)
C4—C5—C6—C7−177.26 (13)C6—C7—C12—C11179.35 (11)
C2—C1—C6—C50.4 (2)C8—C7—C12—C11−54.44 (15)
C2—C1—C6—C7177.41 (13)C11—C10—C13—C14−168.57 (13)
C5—C6—C7—C1272.10 (17)C9—C10—C13—C1468.48 (17)
C1—C6—C7—C12−104.78 (16)C10—C13—C14—C15177.28 (12)
C5—C6—C7—C8−51.96 (18)C13—C14—C15—C16−178.21 (14)
C1—C6—C7—C8131.16 (14)C14—C15—C16—C17−175.27 (14)
C6—C7—C8—C9179.08 (12)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1B···O1i0.84 (2)2.06 (2)2.886 (2)170 (4)
O1—H1A···O1ii0.87 (2)1.99 (2)2.836 (2)165 (4)

Symmetry codes: (i) −x+1, −y, −z; (ii) −x+1, −y+1, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5011).

References

  • Eidenschink, R., Krause, J. & Pohl, L. (1978). US Patent No. 4 130 502.
  • Hu, B. H., Xia, Y. T., Zhou, Y. B., Meng, F. M., Chen, X. & Fu, W. G. (2003). Chinese Patent No. 1 463 961.
  • Rigaku/MSC (2005). CrystalClear and CrystalStructure Rigaku/MSC, The Woodlands, Texas, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Wang, H.-F., Guo, Y., Zhang, H., Zeng, T. & Li, H.-B. (2006). Acta Cryst. E62, o3721–o3722.

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