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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 8| August 2010| Page o2136
https://doi.org/10.1107/S1600536810029417

(2-Methyl­phen­yl)(phen­yl)methanol

B. P. Siddaraju,a H. S. Yathirajan,b‡ B. Narayana,c Seik Weng Ngd and Edward R. T. Tiekinkd*

aDepartment of Chemistry, V. V. Puram College of Science, Bangalore 560 004, India, bDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, cDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri, 574 199, India, and dDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: Edward.Tiekink@gmail.com

(Received 21 July 2010; accepted 23 July 2010; online 31 July 2010)

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 R66(12) loop.

Related literature

For general background to the use of benzhydrols, see: Ohkuma et al. (2000[Ohkuma, T., Koizumi, M., Ikehira, H., Yokozawa, T. & Noyori, R. (2000). Org. Lett. 2, 659-662.]). For the use of the title compound in the perfume and pharmaceutical industries, see: Meguro et al. (1985[Meguro, K., Aizawa, M., Sohda, T., Kawamatsu, Y. & Nagaoka, A. (1985). Chem. Pharm. Bull. 33, 3787-3797.]). For related diphenyl­methanol structures, see: Ferguson et al. (1995[Ferguson, G., Carroll, C. D., Glidewell, C., Zakaria, C. M. & Lough, A. J. (1995). Acta Cryst. B51, 367-377.]).

[Scheme 1]

Experimental

Crystal data

  • C14H14O

  • Mr = 198.25

  • Trigonal, [R \overline 3]

  • 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.971, Tmax = 0.978

  • 6286 measured reflections

  • 2475 independent reflections

  • 2022 reflections with I > 2σ(I)

  • Rint = 0.026
Refinement

  • R[F2 > 2σ(F2)] = 0.045

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O1—H1⋯O1i 0.85 (1) 1.85 (1) 2.6967 (10) 174 (2)
Symmetry code: (i) y, -x+y, -z.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810029417/hb5570Isup2.hkl

checkCIF report


Comment top

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.

Related literature top

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

Experimental top

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 top

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

Structure description top

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.

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

Computing details top

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

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) showing displacement ellipsoids at the 50% probability level.
[Figure 2] Fig. 2. A hexameric aggregate mediated by O–H···O hydrogen bonds (orange dashed lines) in (I). Non-participating H atoms have been omitted.
[Figure 3] 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.
(2-Methylphenyl)(phenyl)methanol top
Crystal data top
C14H14ODx = 1.218 Mg m−3
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 mm−1
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 top
Bruker SMART APEX CCD
diffractometer		2475 independent reflections
Radiation source: fine-focus sealed tube2022 reflections with I > 2σ(I)
Graphite monochromatorRint = 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 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)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121H atoms treated by a mixture of independent and constrained refinement
S = 1.08 w = 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 Å−3
1 restraintΔρmin = −0.30 e Å−3
Crystal data top
C14H14OZ = 18
Mr = 198.25Mo Kα radiation
Trigonal, R3µ = 0.08 mm−1
a = 23.013 (2) ÅT = 100 K
c = 10.6067 (11) Å0.40 × 0.35 × 0.30 mm
V = 4864.8 (7) Å3
Data collection top
Bruker SMART APEX CCD
diffractometer		2475 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		2022 reflections with I > 2σ(I)
Tmin = 0.971, Tmax = 0.978Rint = 0.026
6286 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0451 restraint
wR(F2) = 0.121H atoms treated by a mixture of independent and constrained refinement
S = 1.08Δρmax = 0.43 e Å−3
2475 reflectionsΔρmin = −0.30 e Å−3
141 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*/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) top
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, º) top
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, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O1i0.85 (1)1.85 (1)2.6967 (10)174 (2)
Symmetry code: (i) y, −x+y, −z.

Experimental details

Crystal data
Chemical formulaC14H14O
Mr198.25
Crystal system, space groupTrigonal, R3
Temperature (K)100
a, c (Å)23.013 (2), 10.6067 (11)
V (Å3)4864.8 (7)
Z18
Radiation typeMo Kα
µ (mm−1)0.08
Crystal size (mm)0.40 × 0.35 × 0.30
Data collection
DiffractometerBruker SMART APEX CCD
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.971, 0.978
No. of measured, independent and
observed [I > 2σ(I)] reflections		6286, 2475, 2022
Rint0.026
(sin θ/λ)max (Å−1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.121, 1.08
No. of reflections2475
No. of parameters141
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.43, −0.30

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O1i0.852 (9)1.848 (9)2.6967 (10)174.1 (19)
Symmetry code: (i) y, −x+y, −z.
 

Footnotes

‡Additional correspondence author, e-mail: yathirajan@hotmail.com.

Acknowledgements

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.

References

First citationBrandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
 First citationBruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
 First citationFerguson, G., Carroll, C. D., Glidewell, C., Zakaria, C. M. & Lough, A. J. (1995). Acta Cryst. B51, 367–377.  CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
 First citationMeguro, K., Aizawa, M., Sohda, T., Kawamatsu, Y. & Nagaoka, A. (1985). Chem. Pharm. Bull. 33, 3787–3797.  CrossRef CAS PubMed Google Scholar
 First citationOhkuma, T., Koizumi, M., Ikehira, H., Yokozawa, T. & Noyori, R. (2000). Org. Lett. 2, 659–662.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 8| August 2010| Page o2136
https://doi.org/10.1107/S1600536810029417
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