4-(4-Pentyl­cyclo­hexyl)phenol

Wang, H.-F.; Guo, Y.; Jin, C.-Q.; Le, H.-B.

doi:10.1107/S1600536809024027

organic compounds

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ISSN: 2056-9890

Volume 65| Part 7| July 2009| Page o1717

doi:10.1107/S1600536809024027

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4-(4-Pentylcyclohexyl)phenol

He-Fang Wang,^a ^* Yong Guo,^b Chang-Qing Jin ^a and Hong-Bing Le ^b

^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 ). For applications of phenol derivatives, see: Eidenschink et al. (1978 ); Hu et al. (2003 ).

Experimental

Crystal data

C₁₇H₂₆O
M_r = 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 ) 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[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
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	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); cell refinement: CrystalClear; data reduction: CrystalClear; 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.

Supporting information

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

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

checkCIF report

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).

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

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

C₁₇H₂₆O	F(000) = 544
M_r = 246.38	D_x = 1.136 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3895 reflections
a = 21.002 (4) Å	θ = 1.6–27.9°
b = 5.3281 (11) Å	µ = 0.07 mm⁻¹
c = 13.389 (3) Å	T = 113 K
β = 105.87 (3)°	Block, colourless
V = 1441.2 (5) Å³	0.24 × 0.20 × 0.10 mm
Z = 4

Data collection top

Rigaku Saturn CCD diffractometer	2827 independent reflections
Radiation source: rotating anode	2314 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.040
Detector resolution: 7.31 pixels mm^-1	θ_max = 26.0°, θ_min = 2.0°
ω and ϕ scans	h = −25→22
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −6→6
T_min = 0.984, T_max = 0.993	l = −16→15
10687 measured reflections

Refinement top

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.151	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ²(F_o²) + (0.0738P)² + 0.2552P] where P = (F_o² + 2F_c²)/3
2827 reflections	(Δ/σ)_max = 0.001
170 parameters	Δρ_max = 0.19 e Å⁻³
2 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₁₇H₂₆O	V = 1441.2 (5) Å³
M_r = 246.38	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 21.002 (4) Å	µ = 0.07 mm⁻¹
b = 5.3281 (11) Å	T = 113 K
c = 13.389 (3) Å	0.24 × 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)
T_min = 0.984, T_max = 0.993	R_int = 0.040
10687 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	2 restraints
wR(F²) = 0.151	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	Δρ_max = 0.19 e Å⁻³
2827 reflections	Δρ_min = −0.25 e Å⁻³
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

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.48580 (6)	0.2525 (2)	0.02646 (9)	0.0245 (3)
H1A	0.4889 (19)	0.399 (5)	−0.001 (3)	0.037*	0.50
H1B	0.4982 (19)	0.107 (5)	0.018 (3)	0.037*	0.50
C1	0.41419 (7)	0.0832 (3)	0.23796 (11)	0.0186 (3)
H1	0.4178	−0.0466	0.2878	0.022*
C2	0.45317 (7)	0.0725 (3)	0.16908 (11)	0.0195 (3)
H2	0.4833	−0.0621	0.1723	0.023*
C3	0.44742 (7)	0.2600 (3)	0.09596 (11)	0.0189 (3)
C4	0.40401 (7)	0.4582 (3)	0.09173 (11)	0.0199 (4)
H4	0.4006	0.5876	0.0417	0.024*
C5	0.36564 (7)	0.4663 (3)	0.16100 (11)	0.0197 (4)
H5	0.3357	0.6018	0.1576	0.024*
C6	0.36995 (7)	0.2801 (3)	0.23555 (11)	0.0180 (3)
C7	0.32602 (7)	0.2816 (3)	0.30842 (11)	0.0183 (4)
H7	0.3429	0.1491	0.3621	0.022*
C8	0.32710 (7)	0.5321 (3)	0.36579 (11)	0.0205 (4)
H8A	0.3729	0.5679	0.4074	0.025*
H8B	0.3132	0.6685	0.3142	0.025*
C9	0.28151 (7)	0.5298 (3)	0.43741 (11)	0.0211 (4)
H9A	0.2820	0.6977	0.4694	0.025*
H9B	0.2985	0.4070	0.4939	0.025*
C10	0.20997 (7)	0.4612 (3)	0.37901 (11)	0.0196 (4)
H10	0.1929	0.5933	0.3253	0.024*
C11	0.20944 (8)	0.2107 (3)	0.32292 (12)	0.0215 (4)
H11A	0.2240	0.0759	0.3751	0.026*
H11B	0.1636	0.1722	0.2820	0.026*
C12	0.25437 (7)	0.2132 (3)	0.25071 (12)	0.0208 (4)
H12A	0.2372	0.3362	0.1944	0.025*
H12B	0.2536	0.0455	0.2186	0.025*
C13	0.16400 (8)	0.4506 (3)	0.44966 (12)	0.0227 (4)
H13A	0.1214	0.3758	0.4101	0.027*
H13B	0.1838	0.3369	0.5084	0.027*
C14	0.14968 (8)	0.7019 (3)	0.49357 (12)	0.0238 (4)
H14A	0.1917	0.7737	0.5366	0.029*
H14B	0.1315	0.8191	0.4354	0.029*
C15	0.10106 (8)	0.6811 (3)	0.55919 (12)	0.0258 (4)
H15A	0.0596	0.6038	0.5167	0.031*
H15B	0.1200	0.5676	0.6184	0.031*
C16	0.08453 (8)	0.9309 (3)	0.60091 (13)	0.0273 (4)
H16A	0.1262	1.0150	0.6386	0.033*
H16B	0.0621	1.0395	0.5417	0.033*
C17	0.04046 (9)	0.9051 (4)	0.67340 (14)	0.0402 (5)
H17A	−0.0006	0.8194	0.6371	0.060*
H17B	0.0301	1.0721	0.6953	0.060*
H17C	0.0635	0.8071	0.7345	0.060*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0299 (7)	0.0234 (6)	0.0256 (7)	0.0001 (5)	0.0169 (5)	−0.0007 (5)
C1	0.0216 (8)	0.0165 (7)	0.0183 (8)	−0.0007 (6)	0.0064 (6)	0.0006 (6)
C2	0.0201 (7)	0.0172 (7)	0.0217 (8)	0.0017 (6)	0.0065 (6)	−0.0008 (6)
C3	0.0194 (8)	0.0214 (8)	0.0168 (8)	−0.0025 (6)	0.0066 (6)	−0.0024 (6)
C4	0.0239 (8)	0.0181 (7)	0.0172 (8)	−0.0014 (6)	0.0051 (6)	0.0009 (6)
C5	0.0223 (8)	0.0174 (7)	0.0196 (8)	0.0027 (6)	0.0059 (6)	−0.0005 (6)
C6	0.0194 (8)	0.0189 (8)	0.0152 (8)	−0.0010 (6)	0.0038 (6)	−0.0020 (6)
C7	0.0204 (8)	0.0183 (8)	0.0170 (8)	0.0013 (6)	0.0063 (6)	0.0015 (6)
C8	0.0206 (8)	0.0209 (8)	0.0205 (8)	−0.0013 (6)	0.0066 (6)	−0.0026 (6)
C9	0.0226 (8)	0.0220 (8)	0.0200 (8)	0.0013 (6)	0.0083 (7)	−0.0022 (6)
C10	0.0223 (8)	0.0192 (8)	0.0183 (8)	0.0000 (6)	0.0074 (6)	0.0010 (6)
C11	0.0222 (8)	0.0217 (8)	0.0218 (8)	−0.0030 (6)	0.0081 (7)	−0.0015 (6)
C12	0.0237 (8)	0.0189 (8)	0.0210 (8)	−0.0009 (6)	0.0079 (7)	−0.0017 (6)
C13	0.0246 (8)	0.0229 (8)	0.0230 (8)	−0.0007 (6)	0.0105 (7)	0.0006 (6)
C14	0.0248 (8)	0.0254 (9)	0.0240 (9)	−0.0008 (6)	0.0112 (7)	−0.0006 (6)
C15	0.0282 (9)	0.0278 (9)	0.0249 (9)	0.0001 (7)	0.0134 (7)	0.0007 (7)
C16	0.0257 (9)	0.0326 (10)	0.0260 (9)	−0.0005 (7)	0.0112 (7)	−0.0052 (7)
C17	0.0337 (10)	0.0584 (13)	0.0346 (11)	−0.0006 (9)	0.0193 (9)	−0.0108 (9)

Geometric parameters (Å, º) top

O1—C3	1.3883 (17)	C10—C13	1.5264 (19)
O1—H1A	0.87 (2)	C10—C11	1.530 (2)
O1—H1B	0.84 (2)	C10—H10	1.0000
C1—C2	1.3918 (19)	C11—C12	1.5245 (19)
C1—C6	1.396 (2)	C11—H11A	0.9900
C1—H1	0.9500	C11—H11B	0.9900
C2—C3	1.381 (2)	C12—H12A	0.9900
C2—H2	0.9500	C12—H12B	0.9900
C3—C4	1.386 (2)	C13—C14	1.525 (2)
C4—C5	1.3856 (19)	C13—H13A	0.9900
C4—H4	0.9500	C13—H13B	0.9900
C5—C6	1.393 (2)	C14—C15	1.5222 (19)
C5—H5	0.9500	C14—H14A	0.9900
C6—C7	1.5151 (19)	C14—H14B	0.9900
C7—C12	1.536 (2)	C15—C16	1.520 (2)
C7—C8	1.5373 (19)	C15—H15A	0.9900
C7—H7	1.0000	C15—H15B	0.9900
C8—C9	1.5291 (19)	C16—C17	1.520 (2)
C8—H8A	0.9900	C16—H16A	0.9900
C8—H8B	0.9900	C16—H16B	0.9900
C9—C10	1.536 (2)	C17—H17A	0.9800
C9—H9A	0.9900	C17—H17B	0.9800
C9—H9B	0.9900	C17—H17C	0.9800

C3—O1—H1A	112 (3)	C9—C10—H10	107.9
C3—O1—H1B	112 (3)	C12—C11—C10	112.39 (12)
H1A—O1—H1B	135 (4)	C12—C11—H11A	109.1
C2—C1—C6	121.60 (13)	C10—C11—H11A	109.1
C2—C1—H1	119.2	C12—C11—H11B	109.1
C6—C1—H1	119.2	C10—C11—H11B	109.1
C3—C2—C1	119.14 (13)	H11A—C11—H11B	107.9
C3—C2—H2	120.4	C11—C12—C7	111.98 (12)
C1—C2—H2	120.4	C11—C12—H12A	109.2
C2—C3—C4	120.62 (14)	C7—C12—H12A	109.2
C2—C3—O1	120.02 (13)	C11—C12—H12B	109.2
C4—C3—O1	119.36 (13)	C7—C12—H12B	109.2
C5—C4—C3	119.51 (13)	H12A—C12—H12B	107.9
C5—C4—H4	120.2	C14—C13—C10	115.56 (12)
C3—C4—H4	120.2	C14—C13—H13A	108.4
C4—C5—C6	121.46 (13)	C10—C13—H13A	108.4
C4—C5—H5	119.3	C14—C13—H13B	108.4
C6—C5—H5	119.3	C10—C13—H13B	108.4
C5—C6—C1	117.67 (13)	H13A—C13—H13B	107.5
C5—C6—C7	121.73 (13)	C15—C14—C13	113.12 (13)
C1—C6—C7	120.52 (13)	C15—C14—H14A	109.0
C6—C7—C12	111.11 (11)	C13—C14—H14A	109.0
C6—C7—C8	113.45 (12)	C15—C14—H14B	109.0
C12—C7—C8	109.63 (12)	C13—C14—H14B	109.0
C6—C7—H7	107.5	H14A—C14—H14B	107.8
C12—C7—H7	107.5	C16—C15—C14	113.88 (13)
C8—C7—H7	107.5	C16—C15—H15A	108.8
C9—C8—C7	112.35 (12)	C14—C15—H15A	108.8
C9—C8—H8A	109.1	C16—C15—H15B	108.8
C7—C8—H8A	109.1	C14—C15—H15B	108.8
C9—C8—H8B	109.1	H15A—C15—H15B	107.7
C7—C8—H8B	109.1	C17—C16—C15	113.29 (14)
H8A—C8—H8B	107.9	C17—C16—H16A	108.9
C8—C9—C10	112.06 (12)	C15—C16—H16A	108.9
C8—C9—H9A	109.2	C17—C16—H16B	108.9
C10—C9—H9A	109.2	C15—C16—H16B	108.9
C8—C9—H9B	109.2	H16A—C16—H16B	107.7
C10—C9—H9B	109.2	C16—C17—H17A	109.5
H9A—C9—H9B	107.9	C16—C17—H17B	109.5
C13—C10—C11	110.54 (12)	H17A—C17—H17B	109.5
C13—C10—C9	112.94 (12)	C16—C17—H17C	109.5
C11—C10—C9	109.41 (12)	H17A—C17—H17C	109.5
C13—C10—H10	107.9	H17B—C17—H17C	109.5
C11—C10—H10	107.9

C6—C1—C2—C3	−0.6 (2)	C12—C7—C8—C9	54.21 (15)
C1—C2—C3—C4	0.8 (2)	C7—C8—C9—C10	−55.74 (16)
C1—C2—C3—O1	−179.92 (12)	C8—C9—C10—C13	178.39 (12)
C2—C3—C4—C5	−0.7 (2)	C8—C9—C10—C11	54.80 (16)
O1—C3—C4—C5	−179.99 (12)	C13—C10—C11—C12	179.57 (12)
C3—C4—C5—C6	0.4 (2)	C9—C10—C11—C12	−55.45 (16)
C4—C5—C6—C1	−0.3 (2)	C10—C11—C12—C7	56.67 (16)
C4—C5—C6—C7	−177.26 (13)	C6—C7—C12—C11	179.35 (11)
C2—C1—C6—C5	0.4 (2)	C8—C7—C12—C11	−54.44 (15)
C2—C1—C6—C7	177.41 (13)	C11—C10—C13—C14	−168.57 (13)
C5—C6—C7—C12	72.10 (17)	C9—C10—C13—C14	68.48 (17)
C1—C6—C7—C12	−104.78 (16)	C10—C13—C14—C15	177.28 (12)
C5—C6—C7—C8	−51.96 (18)	C13—C14—C15—C16	−178.21 (14)
C1—C6—C7—C8	131.16 (14)	C14—C15—C16—C17	−175.27 (14)
C6—C7—C8—C9	179.08 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	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.

Experimental details

Crystal data
Chemical formula	C₁₇H₂₆O
M_r	246.38
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	113
a, b, c (Å)	21.002 (4), 5.3281 (11), 13.389 (3)
β (°)	105.87 (3)
V (Å³)	1441.2 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.24 × 0.20 × 0.10

Data collection
Diffractometer	Rigaku Saturn CCD diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2005)
T_min, T_max	0.984, 0.993
No. of measured, independent and observed [I > 2σ(I)] reflections	10687, 2827, 2314
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.151, 1.11
No. of reflections	2827
No. of parameters	170
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	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···A	D—H	H···A	D···A	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.

References

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Volume 65| Part 7| July 2009| Page o1717

doi:10.1107/S1600536809024027

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