4 (2 Phenyl­iso­propyl)­phenol

organic papers

o954

Structure Reports Online

ISSN 1600-5368

4-(2-Phenylisopropyl)phenol

Abdelhak Ettahiri,a_*

Mostafa Abboudi,a

Daphne Merle,b

Monique Perrinb_and

Alain Thozetb

a_{Universite Abdelmalek Essaadi, Faculte des}

Sciences Tetouan, DeÂpartement Chimie, BP 2121 93000 Tetouan, Morocco, andb_{Centre de}

Diffractometrie, Universite Claude Bernard Lyon 1, 43 boulevard du 11 Novembre 1918, 69622 Villeurbanne Cedex, France

Correspondence e-mail: [email protected]

Key indicators

Single-crystal X-ray study

T= 150 K

Mean(C±C) = 0.002 AÊ

Rfactor = 0.049

wRfactor = 0.128

Data-to-parameter ratio = 19.4

For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.

#2004 International Union of Crystallography Printed in Great Britain ± all rights reserved

The structure of 4-cumylphenol, C15H16O, exhibits chains of hydrogen-bonded molecules along thecaxis.

Comment

In the solid state, 4-cumylphenol, (I), crystallizes in space groupR3. The molecules are linked by hydrogen bonds, giving in®nite chains along the c axis; van der Waals interactions between chains have distances of about 3.5 AÊ.p-Cumylphenol was used to synthesize calixarenes with four, six and eight arene units. These macrocycles trap solvent molecules (Gutsche, 1998; Perrinet al., 2003). The conformation of the molecule shows that the two aromatic rings are nearly perpendicular [dihedral angle = 97.71 (5)_{]. Atoms C14 and}

C15 lie 0.204 (3) and ÿ1.588 (3) AÊ, respectively, from the plane of the phenol ring, and 0.708 (1) andÿ0.429 (1) AÊ from the plane of the cumyl ring. The C3ÐC4ÐC7ÐC8 torsion angle value is 47.71 (13)_{. The unit cell contains 18 molecules,}

showing chains around the helicoidal 31 axes. One chain is formed with molecules linked by OÐH O hydrogen bonds as described in Table 1. This type of structure was reported for thymol (2-isopropyl-3-methylphenol; Thozet & Perrin, 1980), and the latter compound crystallized in the same space group. Interactions between chains are found both between phenol rings and between cumyl rings (values 3.51±3.59 AÊ).

Experimental

The title compound was obtained from a (Aldrich) and was dissolved in methanol. Slow evaporation gave single crystals of good quality for X-ray analysis.

Crystal data

C15H16O Mr= 212.28

Rhombohedral,R3

a= 30.989 (4) AÊ

c= 6.500 (1) AÊ

V= 5405.5 (13) AÊ3 Z= 18

Dx= 1.174 Mg mÿ3

MoKradiation Cell parameters from 8097

re¯ections

= 1.0±27.9

= 0.07 mmÿ1 T= 150 (2) K Prism, colorless 0.400.150.15 mm

Data collection

Nonius KappaCCD diffractometer

'scans

Absorption correction: none 15 965 measured re¯ections 2855 independent re¯ections 1948 re¯ections withI> 2(I)

max= 27.9 Rint= 0.075 h=ÿ40!40

k=ÿ40!40

l=ÿ8!8

Re®nement

Re®nement onF2 R[F2_{> 2(F}2_{)] = 0.049} wR(F2_{) = 0.129} S= 0.94 2855 re¯ections 147 parameters

H-atom parameters constrained

w= 1/[2_(F

o2) + (0.0636P)2

+ 5.893P]

whereP= (Fo2+ 2Fc2)/3

(/)max= 0.004

max= 0.17 e AÊÿ3

min=ÿ0.22 e AÊÿ3

Table 1

Hydrogen-bonding geometry (AÊ,_).

DÐH A DÐH H A D A DÐH A

O1ÐH1 O1i _{0.83 1.88 2.710 (1) 173}

Symmetry code: (i)1

3ÿy;xÿyÿ13;zÿ13.

All H atoms were treated as riding on their parent atoms, with CÐ H distances of 0.94 (aromatic) and 0.97 AÊ (methyl), an OÐH distance of 0.83 AÊ, andUiso(H) = 1.2Ueq(Caromatic) and 1.5Ueq(Cmethyl,O).

Data collection:COLLECT(Nonius, 1999); cell re®nement:HKL SCALEPACK(Otwinowski & Minor, 1997); data reduction: HKL SCALEPACK and DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to re®ne structure:SHELXL97 (Sheldrick, 1997); molecular graphics:PLATON(Spek, 1999); software used to prepare material for publication:SHELXL97.

References

Gutsche, C. D. (1998).Calixarenes Revisited, Monographs in Supramolecular Chemistry. London: Royal Society of Chemistry.

Nonius (1999).COLLECT. Nonius BV, Delft, The Netherlands.

Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276,

Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307±326. New York: Academic Press.

Perrin, M., Thozet, A. & Ettahiri, A. (2003).J. Incl. Phenom.47, 11±13. Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of

GoÈttingen, Germany.

Spek, A. L. (1999).PLATON.Utrecht University, The Netherlands. Thozet, A. & Perrin, M. (1980).Acta Cryst.B36, 1444±1445.

Figure 1

supporting information

sup-1 Acta Cryst. (2004). E60, o954–o955

supporting information

Acta Cryst. (2004). E60, o954–o955 [https://doi.org/10.1107/S1600536804010621]

4-(2-Phenylisopropyl)phenol

Abdelhak Ettahiri, Mostafa Abboudi, Daphne Merle, Monique Perrin and Alain Thozet

4-(2-phenylisopropyl)phenol

Crystal data

C15H16O Mr = 212.28 Hexagonal, R3 a = 30.989 (4) Å c = 6.500 (1) Å V = 5405.5 (13) Å3 Z = 18

F(000) = 2052

Dx = 1.174 Mg m−3

Mo Kα radiation, λ = 0.71069 Å Cell parameters from 8097 reflections θ = 1.0–27.9°

µ = 0.07 mm−1 T = 150 K Prism, colorless 0.40 × 0.15 × 0.15 mm

Data collection

KappaCCD diffractometer

Radiation source: fine-focus sealed tube Horizonally mounted graphite crystal

monochromator

Detector resolution: 9 pixels mm-1 CCD scans

2855 measured reflections

2855 independent reflections 1948 reflections with I > 2σ(I) Rint = 0.000

θmax = 27.9°, θmin = 3.5° h = −40→19

k = 0→40 l = 0→8

Refinement

Refinement on F2 Least-squares matrix: full R[F2 _{> 2σ(F}2_{)] = 0.049} wR(F2_{) = 0.129} S = 0.94 2855 reflections 147 parameters 0 restraints

Primary atom site location: structure-invariant direct methods

Secondary atom site location: difference Fourier map

Hydrogen site location: inferred from neighbouring sites

H-atom parameters constrained w = 1/[σ2_(Fo2_{) + (0.0636P)}2 _{+ 5.893P]}

where P = (Fo2 _{+ 2Fc}2_)/3 (Δ/σ)max = 0.004

Δρmax = 0.17 e Å−3 Δρmin = −0.22 e Å−3

Special details

Experimental. Diffractometer equiped with an area detector. phi scans and omega scans during 20 s with 2 ° steps Crystal to detector distance: 30 mm

Refinement. Refinement of F2 _{against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F}2_, conventional R-factors R are based on F, with F set to zero for negative F2_{. The threshold expression of F}2 _{> σ(F}2_{) 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₎

x y z Uiso*/Ueq

O1 0.34804 (4) 0.03489 (4) 0.01722 (16) 0.0336 (3)

H1 0.3351 0.0193 −0.0902 0.050*

C1 0.36952 (5) 0.08549 (6) −0.0195 (2) 0.0268 (3)

C2 0.39345 (6) 0.11810 (6) 0.1415 (2) 0.0287 (4)

H2 0.3958 0.1059 0.2708 0.034*

C3 0.41382 (6) 0.16878 (6) 0.1110 (2) 0.0283 (4)

H3 0.4296 0.1906 0.2218 0.034*

C4 0.41168 (5) 0.18850 (6) −0.0795 (2) 0.0268 (3)

C5 0.38846 (6) 0.15488 (6) −0.2388 (2) 0.0311 (4)

H5 0.3868 0.1670 −0.3696 0.037*

C6 0.36758 (6) 0.10389 (6) −0.2103 (2) 0.0316 (4)

H6 0.3521 0.0819 −0.3210 0.038*

C7 0.43124 (6) 0.24464 (6) −0.1009 (2) 0.0290 (4)

C8 0.48275 (6) 0.27424 (6) −0.0007 (2) 0.0261 (3)

C9 0.52031 (6) 0.26461 (6) −0.0604 (2) 0.0281 (3)

H9 0.5130 0.2388 −0.1547 0.034*

C10 0.56813 (6) 0.29222 (6) 0.0165 (2) 0.0312 (4)

H10 0.5930 0.2852 −0.0262 0.037*

C11 0.57953 (6) 0.33019 (6) 0.1564 (2) 0.0338 (4)

H11 0.6122 0.3494 0.2067 0.041*

C12 0.54276 (7) 0.33956 (6) 0.2211 (2) 0.0363 (4)

H12 0.5501 0.3647 0.3185 0.044*

C13 0.49467 (7) 0.31187 (6) 0.1426 (2) 0.0338 (4)

H13 0.4699 0.3187 0.1873 0.041*

C14 0.43700 (7) 0.26118 (6) −0.3281 (2) 0.0365 (4)

H14A 0.4046 0.2446 −0.3946 0.055*

H14B 0.4592 0.2523 −0.3978 0.055*

H14C 0.4508 0.2970 −0.3347 0.055*

C15 0.39263 (7) 0.25528 (7) 0.0002 (3) 0.0393 (4)

H15A 0.3910 0.2485 0.1465 0.059*

H15B 0.3602 0.2341 −0.0612 0.059*

H15C 0.4023 0.2900 −0.0210 0.059*

Atomic displacement parameters (Å2₎

U11 _U22 _U33 _U12 _U13 _U23

O1 0.0369 (7) 0.0304 (6) 0.0304 (6) 0.0145 (5) −0.0064 (5) 0.0001 (5)

C1 0.0223 (8) 0.0298 (8) 0.0289 (7) 0.0136 (7) −0.0001 (6) 0.0020 (6)

C2 0.0265 (8) 0.0365 (9) 0.0222 (7) 0.0150 (7) −0.0014 (6) 0.0046 (6)

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sup-3 Acta Cryst. (2004). E60, o954–o955

C4 0.0226 (8) 0.0327 (9) 0.0260 (7) 0.0144 (7) 0.0013 (6) 0.0019 (6)

C5 0.0357 (9) 0.0363 (9) 0.0226 (7) 0.0189 (8) −0.0029 (6) 0.0027 (6)

C6 0.0340 (9) 0.0358 (9) 0.0247 (8) 0.0172 (8) −0.0080 (6) −0.0041 (6)

C7 0.0315 (9) 0.0320 (9) 0.0264 (8) 0.0181 (7) −0.0003 (6) 0.0016 (6)

C8 0.0308 (8) 0.0254 (8) 0.0228 (7) 0.0146 (7) 0.0023 (6) 0.0034 (6)

C9 0.0319 (8) 0.0262 (8) 0.0242 (7) 0.0131 (7) 0.0009 (6) −0.0012 (6)

C10 0.0299 (9) 0.0329 (9) 0.0292 (8) 0.0146 (7) 0.0032 (6) 0.0036 (6)

C11 0.0350 (9) 0.0278 (9) 0.0305 (8) 0.0096 (7) −0.0051 (7) 0.0022 (7)

C12 0.0498 (11) 0.0274 (9) 0.0297 (8) 0.0178 (8) −0.0053 (7) −0.0048 (7)

C13 0.0435 (10) 0.0348 (9) 0.0293 (8) 0.0242 (8) 0.0017 (7) −0.0015 (7)

C14 0.0414 (10) 0.0368 (10) 0.0313 (9) 0.0196 (8) −0.0032 (7) 0.0055 (7)

C15 0.0364 (10) 0.0468 (11) 0.0431 (10) 0.0271 (9) 0.0009 (7) 0.0010 (8)

Geometric parameters (Å, º)

O1—C1 1.3838 (18) C8—C9 1.394 (2)

O1—H1 0.8300 C9—C10 1.382 (2)

C1—C6 1.379 (2) C9—H9 0.9400

C1—C2 1.385 (2) C10—C11 1.386 (2)

C2—C3 1.383 (2) C10—H10 0.9400

C2—H2 0.9400 C11—C12 1.375 (2)

C3—C4 1.397 (2) C11—H11 0.9400

C3—H3 0.9400 C12—C13 1.392 (2)

C4—C5 1.388 (2) C12—H12 0.9400

C4—C7 1.536 (2) C13—H13 0.9400

C5—C6 1.388 (2) C14—H14A 0.9700

C5—H5 0.9400 C14—H14B 0.9700

C6—H6 0.9400 C14—H14C 0.9700

C7—C8 1.533 (2) C15—H15A 0.9700

C7—C15 1.538 (2) C15—H15B 0.9700

C7—C14 1.544 (2) C15—H15C 0.9700

C8—C13 1.390 (2)

C1—O1—H1 109.5 C10—C9—C8 121.25 (14)

C6—C1—O1 121.89 (14) C10—C9—H9 119.4

C6—C1—C2 119.75 (15) C8—C9—H9 119.4

O1—C1—C2 118.36 (13) C9—C10—C11 120.13 (15)

C3—C2—C1 119.62 (13) C9—C10—H10 119.9

C3—C2—H2 120.2 C11—C10—H10 119.9

C1—C2—H2 120.2 C12—C11—C10 119.59 (15)

C2—C3—C4 121.95 (14) C12—C11—H11 120.2

C2—C3—H3 119.0 C10—C11—H11 120.2

C4—C3—H3 119.0 C11—C12—C13 120.16 (15)

C5—C4—C3 116.94 (14) C11—C12—H12 119.9

C5—C4—C7 123.08 (13) C13—C12—H12 119.9

C3—C4—C7 119.83 (13) C8—C13—C12 121.06 (15)

C4—C5—C6 121.78 (13) C8—C13—H13 119.5

C6—C5—H5 119.1 C7—C14—H14A 109.5

C1—C6—C5 119.92 (14) C7—C14—H14B 109.5

C1—C6—H6 120.0 H14A—C14—H14B 109.5

C5—C6—H6 120.0 C7—C14—H14C 109.5

C8—C7—C4 110.03 (12) H14A—C14—H14C 109.5

C8—C7—C15 112.26 (13) H14B—C14—H14C 109.5

C4—C7—C15 107.18 (13) C7—C15—H15A 109.5

C8—C7—C14 107.16 (13) C7—C15—H15B 109.5

C4—C7—C14 112.16 (13) H15A—C15—H15B 109.5

C15—C7—C14 108.10 (13) C7—C15—H15C 109.5

C13—C8—C9 117.78 (15) H15A—C15—H15C 109.5

C13—C8—C7 123.17 (14) H15B—C15—H15C 109.5

C9—C8—C7 119.00 (13)

C6—C1—C2—C3 2.0 (2) C3—C4—C7—C14 166.89 (14)

O1—C1—C2—C3 −177.87 (13) C4—C7—C8—C13 −128.63 (15)

C1—C2—C3—C4 −0.9 (2) C15—C7—C8—C13 −9.4 (2)

C2—C3—C4—C5 −0.6 (2) C14—C7—C8—C13 109.18 (16)

C2—C3—C4—C7 175.24 (14) C4—C7—C8—C9 53.86 (17)

C3—C4—C5—C6 1.0 (2) C15—C7—C8—C9 173.13 (14)

C7—C4—C5—C6 −174.70 (15) C14—C7—C8—C9 −68.33 (17)

O1—C1—C6—C5 178.25 (14) C13—C8—C9—C10 −1.4 (2)

C2—C1—C6—C5 −1.7 (2) C7—C8—C9—C10 176.21 (14)

C4—C5—C6—C1 0.1 (2) C8—C9—C10—C11 0.3 (2)

C5—C4—C7—C8 −136.75 (15) C9—C10—C11—C12 1.2 (2)

C3—C4—C7—C8 47.71 (18) C10—C11—C12—C13 −1.6 (2)

C5—C4—C7—C15 100.92 (17) C9—C8—C13—C12 1.1 (2)

C3—C4—C7—C15 −74.61 (17) C7—C8—C13—C12 −176.45 (14)

C5—C4—C7—C14 −17.6 (2) C11—C12—C13—C8 0.4 (2)

Hydrogen-bond geometry (Å, º)

D—H···A D—H H···A D···A D—H···A

O1—H1···O1i _{0.83 1.88 2.710 (1) 173}