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Acta Crystallogr Sect E Struct Rep Online. 2010 August 1; 66(Pt 8): o2136.
Published online 2010 July 31. doi:  10.1107/S1600536810029417
PMCID: PMC3007446

(2-Methyl­phen­yl)(phen­yl)methanol

Abstract

In the title compound, C14H14O, the two benzene rings are almost orthogonal [dihedral angle = 87.78 (8) °]. The hy­droxy group lies approximately in the plane of its attached benzene ring [O—C—C—C torsion angle = −17.47 (17)°], and the hydroxyl and methyl groups lie to the same side of the mol­ecule and are gauche to each other. In the crystal, a hexa­meric aggregate mediated by a ring of six O—H(...)O hydrogen bonds occurs, generating an R 6 6(12) loop.

Related literature

For general background to the use of benzhydrols, see: Ohkuma et al. (2000 [triangle]). For the use of the title compound in the perfume and pharmaceutical industries, see: Meguro et al. (1985 [triangle]). For related diphenyl­methanol structures, see: Ferguson et al. (1995 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o2136-scheme1.jpg

Experimental

Crystal data

  • C14H14O
  • M r = 198.25
  • Trigonal, An external file that holds a picture, illustration, etc.
Object name is e-66-o2136-efi1.jpg
  • a = 23.013 (2) Å
  • c = 10.6067 (11) Å
  • V = 4864.8 (7) Å3
  • Z = 18
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 100 K
  • 0.40 × 0.35 × 0.30 mm

Data collection

  • Bruker SMART APEX CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.971, T max = 0.978
  • 6286 measured reflections
  • 2475 independent reflections
  • 2022 reflections with I > 2σ(I)
  • R int = 0.026

Refinement

  • R[F 2 > 2σ(F 2)] = 0.045
  • wR(F 2) = 0.121
  • S = 1.08
  • 2475 reflections
  • 141 parameters
  • 1 restraint
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.43 e Å−3
  • Δρmin = −0.30 e Å−3

Data collection: APEX2 (Bruker, 2008 [triangle]); cell refinement: SAINT (Bruker, 2008 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 (Farrugia, 1997 [triangle]) and DIAMOND (Brandenburg, 2006 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2010 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks general, I. DOI: 10.1107/S1600536810029417/hb5570sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810029417/hb5570Isup2.hkl

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

Acknowledgments

HSY thanks the University of Mysore for research facilities and for sabbatical leave. BPS thanks R. L. Fine Chemicals for the gift of the title compound. The authors are also grateful to the University of Malaya for support of the crystallographic facility.

supplementary crystallographic information

Comment

Benzhydrols are widely used as intermediates for the synthesis of pharmaceuticals (Ohkuma et al., 2000), including drugs such as diphenhydramine, orphenadrine, diphenidol and phenyltoloxamine. The crystal structures and hydrogen bonding in some diphenylmethanols have been reported (Ferguson et al., 1995). The title compound, phenyl-o-tolyl-methanol, (I), is a derivative of diphenylmethanol and it has use in the perfume and pharmaceutical industries (Meguro et al., 1985).

The molecular structure of (I), Fig. 1, features a tertiary C7 atom connected to benzene and o-tolyl rings. With reference to the benzene ring, the O1 atom is nearly co-planar as seen in the O1–C8–C9–C14 torsion angle of -17.47 (17) °. By contrast, the o-tolyl group is almost orthogonal as seen in the C1–C8–C9–C10 torsion angle of -80.12 (15) °; the dihedral angle formed between the two least-squares planes is 87.78 (8) °. While lying to the same side of the molecule, the hydroxy and methyl groups are gauche.

The crystal packing is dominated by O–H···O hydrogen bonding, Table 1. Almost planar 12-membered rings comprising six O–H···O hydrogen bonds are found, each disposed about a site of symmetry, 3, Fig. 2. The hexameric aggregates stack in columns aligned along the c axis, Fig. 3.

Experimental

The title compound was obtained as a gift from R. L. Fine Chemicals, Bangalore, India. Colourless blocks of (I) were obtained by the slow evaporation of its acetonitrile solution; m.pt. 369–372 K.

Refinement

Carbon-bound H-atoms were placed in calculated positions (C—H 0.95 to 1.00 Å) and were included in the refinement in the riding model approximation, with Uiso(H) set to 1.2 to 1.5Uequiv(C). The O-bound H-atom was located in a difference Fourier map, and was refined with a distance restraint of O–H 0.84±0.01 Å; the Uiso value was freely refined

Figures

Fig. 1.
The molecular structure of (I) showing displacement ellipsoids at the 50% probability level.
Fig. 2.
A hexameric aggregate mediated by O–H···O hydrogen bonds (orange dashed lines) in (I). Non-participating H atoms have been omitted.
Fig. 3.
The unit-cell contents shown in projection down the c axis in (I). The O–H···O hydrogen bonding is shown as orange dashed lines.

Crystal data

C14H14ODx = 1.218 Mg m3
Mr = 198.25Mo Kα radiation, λ = 0.71073 Å
Trigonal, R3Cell parameters from 2551 reflections
Hall symbol: -R 3θ = 2.8–28.3°
a = 23.013 (2) ŵ = 0.08 mm1
c = 10.6067 (11) ÅT = 100 K
V = 4864.8 (7) Å3Block, colourless
Z = 180.40 × 0.35 × 0.30 mm
F(000) = 1908

Data collection

Bruker SMART APEX CCD diffractometer2475 independent reflections
Radiation source: fine-focus sealed tube2022 reflections with I > 2σ(I)
graphiteRint = 0.026
ω scansθmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −28→28
Tmin = 0.971, Tmax = 0.978k = −29→14
6286 measured reflectionsl = −13→13

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)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121H atoms treated by a mixture of independent and constrained refinement
S = 1.08w = 1/[σ2(Fo2) + (0.0533P)2 + 4.2609P] where P = (Fo2 + 2Fc2)/3
2475 reflections(Δ/σ)max < 0.001
141 parametersΔρmax = 0.43 e Å3
1 restraintΔρmin = −0.30 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*/Ueq
O10.13170 (5)0.08915 (5)0.01453 (9)0.0229 (2)
H10.1201 (9)0.0483 (5)0.0010 (18)0.043 (5)*
C10.20865 (7)0.19098 (7)0.11187 (14)0.0237 (3)
C20.18864 (8)0.21209 (7)0.21715 (15)0.0306 (3)
H20.16370.18080.28160.037*
C30.20471 (9)0.27864 (8)0.22928 (18)0.0417 (4)
H30.19110.29300.30180.050*
C40.24081 (9)0.32372 (8)0.1346 (2)0.0495 (5)
H40.25230.36940.14230.059*
C50.26018 (8)0.30288 (8)0.0295 (2)0.0433 (5)
H50.28470.3344−0.03490.052*
C60.24463 (7)0.23669 (7)0.01529 (16)0.0321 (4)
C70.26458 (8)0.21578 (9)−0.10289 (17)0.0422 (4)
H7A0.28780.2545−0.15910.063*
H7B0.22440.1806−0.14500.063*
H7C0.29460.1984−0.08190.063*
C80.18897 (6)0.11780 (6)0.09612 (12)0.0206 (3)
H80.22640.11620.05150.025*
C90.17524 (6)0.07865 (6)0.21775 (12)0.0183 (3)
C100.22851 (7)0.08429 (7)0.28925 (13)0.0247 (3)
H100.27330.11480.26420.030*
C110.21660 (7)0.04561 (7)0.39708 (14)0.0276 (3)
H110.25330.05000.44570.033*
C120.15144 (7)0.00071 (7)0.43395 (13)0.0247 (3)
H120.1433−0.02630.50690.030*
C130.09838 (7)−0.00461 (7)0.36404 (13)0.0229 (3)
H130.0536−0.03500.38940.027*
C140.11032 (7)0.03426 (6)0.25682 (13)0.0207 (3)
H140.07350.03040.20950.025*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0260 (5)0.0200 (5)0.0247 (5)0.0130 (4)−0.0060 (4)−0.0017 (4)
C10.0180 (6)0.0186 (6)0.0340 (8)0.0087 (5)−0.0060 (5)0.0017 (5)
C20.0317 (8)0.0235 (7)0.0397 (9)0.0161 (6)−0.0096 (6)−0.0041 (6)
C30.0449 (10)0.0297 (8)0.0577 (11)0.0241 (8)−0.0221 (8)−0.0149 (8)
C40.0386 (10)0.0164 (7)0.0895 (15)0.0106 (7)−0.0297 (10)−0.0038 (8)
C50.0261 (8)0.0226 (8)0.0717 (13)0.0051 (6)−0.0108 (8)0.0127 (8)
C60.0162 (6)0.0257 (7)0.0487 (10)0.0062 (6)−0.0050 (6)0.0106 (7)
C70.0275 (8)0.0477 (10)0.0491 (10)0.0171 (8)0.0090 (7)0.0230 (8)
C80.0190 (6)0.0213 (6)0.0239 (7)0.0118 (5)−0.0006 (5)0.0022 (5)
C90.0205 (6)0.0158 (6)0.0209 (6)0.0107 (5)−0.0001 (5)−0.0007 (5)
C100.0188 (6)0.0233 (7)0.0301 (7)0.0091 (5)−0.0017 (5)0.0023 (5)
C110.0246 (7)0.0302 (8)0.0289 (8)0.0144 (6)−0.0055 (6)0.0027 (6)
C120.0301 (7)0.0228 (7)0.0234 (7)0.0148 (6)−0.0001 (5)0.0027 (5)
C130.0220 (7)0.0217 (6)0.0237 (7)0.0100 (5)0.0020 (5)−0.0008 (5)
C140.0193 (6)0.0218 (6)0.0230 (7)0.0118 (5)−0.0014 (5)−0.0016 (5)

Geometric parameters (Å, °)

O1—C81.4323 (16)C7—H7B0.9800
O1—H10.852 (9)C7—H7C0.9800
C1—C21.385 (2)C8—C91.5137 (18)
C1—C61.404 (2)C8—H81.0000
C1—C81.5188 (18)C9—C141.3862 (18)
C2—C31.390 (2)C9—C101.3911 (18)
C2—H20.9500C10—C111.390 (2)
C3—C41.383 (3)C10—H100.9500
C3—H30.9500C11—C121.386 (2)
C4—C51.373 (3)C11—H110.9500
C4—H40.9500C12—C131.3806 (19)
C5—C61.388 (2)C12—H120.9500
C5—H50.9500C13—C141.3868 (19)
C6—C71.495 (3)C13—H130.9500
C7—H7A0.9800C14—H140.9500
C8—O1—H1108.5 (13)O1—C8—C9111.77 (10)
C2—C1—C6120.03 (13)O1—C8—C1105.81 (10)
C2—C1—C8120.69 (13)C9—C8—C1115.10 (11)
C6—C1—C8119.20 (13)O1—C8—H8108.0
C1—C2—C3120.59 (16)C9—C8—H8108.0
C1—C2—H2119.7C1—C8—H8108.0
C3—C2—H2119.7C14—C9—C10118.73 (12)
C4—C3—C2119.23 (18)C14—C9—C8121.37 (12)
C4—C3—H3120.4C10—C9—C8119.81 (11)
C2—C3—H3120.4C11—C10—C9120.43 (13)
C5—C4—C3120.38 (15)C11—C10—H10119.8
C5—C4—H4119.8C9—C10—H10119.8
C3—C4—H4119.8C12—C11—C10120.20 (13)
C4—C5—C6121.39 (17)C12—C11—H11119.9
C4—C5—H5119.3C10—C11—H11119.9
C6—C5—H5119.3C13—C12—C11119.60 (13)
C5—C6—C1118.37 (16)C13—C12—H12120.2
C5—C6—C7119.48 (15)C11—C12—H12120.2
C1—C6—C7122.12 (14)C12—C13—C14120.14 (13)
C6—C7—H7A109.5C12—C13—H13119.9
C6—C7—H7B109.5C14—C13—H13119.9
H7A—C7—H7B109.5C9—C14—C13120.89 (12)
C6—C7—H7C109.5C9—C14—H14119.6
H7A—C7—H7C109.5C13—C14—H14119.6
H7B—C7—H7C109.5
C6—C1—C2—C3−1.0 (2)C6—C1—C8—C9157.52 (12)
C8—C1—C2—C3−177.73 (13)O1—C8—C9—C14−17.47 (17)
C1—C2—C3—C40.3 (2)C1—C8—C9—C14103.27 (14)
C2—C3—C4—C50.4 (2)O1—C8—C9—C10159.14 (12)
C3—C4—C5—C6−0.3 (2)C1—C8—C9—C10−80.12 (15)
C4—C5—C6—C1−0.4 (2)C14—C9—C10—C110.6 (2)
C4—C5—C6—C7177.76 (15)C8—C9—C10—C11−176.11 (12)
C2—C1—C6—C51.0 (2)C9—C10—C11—C120.4 (2)
C8—C1—C6—C5177.84 (13)C10—C11—C12—C13−1.0 (2)
C2—C1—C6—C7−177.07 (14)C11—C12—C13—C140.7 (2)
C8—C1—C6—C7−0.3 (2)C10—C9—C14—C13−0.92 (19)
C2—C1—C8—O198.25 (14)C8—C9—C14—C13175.72 (12)
C6—C1—C8—O1−78.54 (14)C12—C13—C14—C90.3 (2)
C2—C1—C8—C9−25.70 (17)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1···O1i0.85 (1)1.85 (1)2.6967 (10)174 (2)

Symmetry codes: (i) y, −x+y, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5570).

References

  • Brandenburg, K. (2006). DIAMOND Crystal Impact GbR, Bonn, Germany.
  • Bruker (2008). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Ferguson, G., Carroll, C. D., Glidewell, C., Zakaria, C. M. & Lough, A. J. (1995). Acta Cryst. B51, 367–377.
  • Meguro, K., Aizawa, M., Sohda, T., Kawamatsu, Y. & Nagaoka, A. (1985). Chem. Pharm. Bull.33, 3787–3797. [PubMed]
  • Ohkuma, T., Koizumi, M., Ikehira, H., Yokozawa, T. & Noyori, R. (2000). Org. Lett.2, 659–662. [PubMed]
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2010). J. Appl. Cryst.43, 920–925.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography