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

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ISSN: 2056-9890

4-(4-Pentyl­cyclo­hexyl)phenol

aSchool of Chemical Engineering and Technology, Hebei University of Technology, Tianjin 300131, People's Republic of China, and bCNOOC Tianjin Research and Design Institute of Chemical Industry, Tianjin 300131, People's Republic of China
*Correspondence e-mail: whf0618@163.com

(Received 19 June 2009; accepted 23 June 2009; online 27 June 2009)

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[Wang, H.-F., Guo, Y., Zhang, H., Zeng, T. & Li, H.-B. (2006). Acta Cryst. E62, o3721-o3722.]). For applications of phenol derivatives, see: Eidenschink et al. (1978[Eidenschink, R., Krause, J. & Pohl, L. (1978). US Patent No. 4 130 502.]); Hu et al. (2003[Hu, B. H., Xia, Y. T., Zhou, Y. B., Meng, F. M., Chen, X. & Fu, W. G. (2003). Chinese Patent No. 1 463 961.]).

[Scheme 1]

Experimental

Crystal data
  • C17H26O

  • Mr = 246.38

  • Monoclinic, P 21 /c

  • 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[Rigaku/MSC (2005). CrystalClear and CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.]) Tmin = 0.984, Tmax = 0.993

  • 10687 measured reflections

  • 2827 independent reflections

  • 2314 reflections with I > 2σ(I)

  • Rint = 0.040

Refinement
  • R[F2 > 2σ(F2)] = 0.056

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1B⋯O1i 0.84 (2) 2.06 (2) 2.886 (2) 170 (4)
O1—H1A⋯O1ii 0.87 (2) 1.99 (2) 2.836 (2) 165 (4)
Symmetry codes: (i) -x+1, -y, -z; (ii) -x+1, -y+1, -z.

Data collection: CrystalClear (Rigaku/MSC, 2005[Rigaku/MSC (2005). CrystalClear and CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.]); cell refinement: CrystalClear; data reduction: CrystalClear; 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

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).

Related literature top

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

Refinement top

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).

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); 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. 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.
4-(4-Pentylcyclohexyl)phenol top
Crystal data top
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 top
Rigaku Saturn CCD
diffractometer
2827 independent reflections
Radiation source: rotating anode2314 reflections with I > 2σ(I)
Confocal monochromatorRint = 0.040
Detector resolution: 7.31 pixels mm-1θmax = 26.0°, θmin = 2.0°
ω and ϕ scansh = 2522
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2005)
k = 66
Tmin = 0.984, Tmax = 0.993l = 1615
10687 measured reflections
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)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.151H atoms treated by a mixture of independent and constrained refinement
S = 1.11 w = 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
Crystal data top
C17H26OV = 1441.2 (5) Å3
Mr = 246.38Z = 4
Monoclinic, P21/cMo Kα radiation
a = 21.002 (4) ŵ = 0.07 mm1
b = 5.3281 (11) ÅT = 113 K
c = 13.389 (3) Å0.24 × 0.20 × 0.10 mm
β = 105.87 (3)°
Data collection top
Rigaku Saturn CCD
diffractometer
2827 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2005)
2314 reflections with I > 2σ(I)
Tmin = 0.984, Tmax = 0.993Rint = 0.040
10687 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0562 restraints
wR(F2) = 0.151H atoms treated by a mixture of independent and constrained refinement
S = 1.11Δρmax = 0.19 e Å3
2827 reflectionsΔρmin = 0.25 e Å3
170 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*/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)
H10.41780.04660.28780.022*
C20.45317 (7)0.0725 (3)0.16908 (11)0.0195 (3)
H20.48330.06210.17230.023*
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)
H17A0.00060.81940.63710.060*
H17B0.03011.07210.69530.060*
H17C0.06350.80710.73450.060*
Atomic displacement parameters (Å2) top
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, º) top
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—C30.6 (2)C12—C7—C8—C954.21 (15)
C1—C2—C3—C40.8 (2)C7—C8—C9—C1055.74 (16)
C1—C2—C3—O1179.92 (12)C8—C9—C10—C13178.39 (12)
C2—C3—C4—C50.7 (2)C8—C9—C10—C1154.80 (16)
O1—C3—C4—C5179.99 (12)C13—C10—C11—C12179.57 (12)
C3—C4—C5—C60.4 (2)C9—C10—C11—C1255.45 (16)
C4—C5—C6—C10.3 (2)C10—C11—C12—C756.67 (16)
C4—C5—C6—C7177.26 (13)C6—C7—C12—C11179.35 (11)
C2—C1—C6—C50.4 (2)C8—C7—C12—C1154.44 (15)
C2—C1—C6—C7177.41 (13)C11—C10—C13—C14168.57 (13)
C5—C6—C7—C1272.10 (17)C9—C10—C13—C1468.48 (17)
C1—C6—C7—C12104.78 (16)C10—C13—C14—C15177.28 (12)
C5—C6—C7—C851.96 (18)C13—C14—C15—C16178.21 (14)
C1—C6—C7—C8131.16 (14)C14—C15—C16—C17175.27 (14)
C6—C7—C8—C9179.08 (12)
Hydrogen-bond geometry (Å, º) top
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.

Experimental details

Crystal data
Chemical formulaC17H26O
Mr246.38
Crystal system, space groupMonoclinic, P21/c
Temperature (K)113
a, b, c (Å)21.002 (4), 5.3281 (11), 13.389 (3)
β (°) 105.87 (3)
V3)1441.2 (5)
Z4
Radiation typeMo Kα
µ (mm1)0.07
Crystal size (mm)0.24 × 0.20 × 0.10
Data collection
DiffractometerRigaku Saturn CCD
diffractometer
Absorption correctionMulti-scan
(CrystalClear; Rigaku/MSC, 2005)
Tmin, Tmax0.984, 0.993
No. of measured, independent and
observed [I > 2σ(I)] reflections
10687, 2827, 2314
Rint0.040
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.056, 0.151, 1.11
No. of reflections2827
No. of parameters170
No. of restraints2
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.19, 0.25

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
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.
 

References

First citationEidenschink, R., Krause, J. & Pohl, L. (1978). US Patent No. 4 130 502.
First citationHu, B. H., Xia, Y. T., Zhou, Y. B., Meng, F. M., Chen, X. & Fu, W. G. (2003). Chinese Patent No. 1 463 961.
First citationRigaku/MSC (2005). CrystalClear and CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationWang, H.-F., Guo, Y., Zhang, H., Zeng, T. & Li, H.-B. (2006). Acta Cryst. E62, o3721–o3722.  Web of Science CSD CrossRef IUCr Journals

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ISSN: 2056-9890
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