(2-Methyl-phen-yl)(phen-yl)methanol.

Abstract

In the title compound, C(14)H(14)O, the two benzene rings are almost orthogonal [dihedral angle = 87.78 (8) °]. The hy-droxy 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 mol-ecule and are gauche to each other. In the crystal, a hexa-meric aggregate mediated by a ring of six O-H⋯O hydrogen bonds occurs, generating an R(6) (6)(12) loop.

Full text

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(2-Methylphenyl)(phenyl)methanol
B. P. Siddaraju,aH. S. Yathirajan,b‡ B. Narayana,c
Seik Weng Ngdand 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, anddDepartment of Chemistry, University of
Malaya, 50603 Kuala Lumpur, Malaysia
Correspondence e-mail: Edward.Tiekink@gmail.com
Received 21 July 2010; accepted 23 July 2010
Key indicators: single-crystal X-ray study; T = 100 K; mean ?(C–C) = 0.002 A ˚;
R factor = 0.045; wR factor = 0.121; data-to-parameter ratio = 17.6.
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 R6
6(12) loop.
Related literature
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 relateddiphenylmethanol
Ferguson et al. (1995).
structures,see:
Experimental
Crystal data
C14H14O
Mr= 198.25
Trigonal, R3
a = 23.013 (2) A˚
c = 10.6067 (11) A˚
V = 4864.8 (7) A˚3
Z = 18
Mo K? radiation
? = 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)
Tmin= 0.971, Tmax= 0.978
6286 measured reflections
2475 independent reflections
2022 reflections with I > 2?(I)
Rint= 0.026
Refinement
R[F2> 2?(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
??max= 0.43 e A˚?3
??min= ?0.30 e A˚?3
Table 1
Hydrogen-bond geometry (A˚,?).
D—H???A
O1—H1???O1i
Symmetry code: (i) y;?x þ y;?z.
D—HH???AD???AD—H???A
0.85 (1)1.85 (1) 2.6967 (10)174 (2)
Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT
(Bruker, 2008); data reduction: SAINT; program(s) used to solve
structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine
structure: SHELXL97(Sheldrick,
ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006);
software used to prepare material for publication: publCIF (Westrip,
2010).
2008); moleculargraphics:
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 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.
Ohkuma, T., Koizumi, M., Ikehira, H., Yokozawa, T. & Noyori, R. (2000). Org.
Lett. 2, 659–662.
Sheldrick, G. M. (1996). SADABS. University of Go ¨ttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.
organic compounds
o2136
Siddaraju et al.
doi:10.1107/S1600536810029417
Acta Cryst. (2010). E66, o2136
Acta Crystallographica Section E
Structure Reports
Online
ISSN 1600-5368
‡ Additional correspondence author, e-mail: yathirajan@hotmail.com.

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Acta Cryst. (2010). E66, o2136 [ doi:10.1107/S1600536810029417 ]
(2-Methylphenyl)(phenyl)methanol
B. P. Siddaraju, H. S. Yathirajan, B. Narayana, S. W. Ng and E. R. T. Tiekink
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.

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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 hydro-
gen bonding is shown as orange dashed lines.
(2-Methylphenyl)(phenyl)methanol
Crystal data
C14H14O
Dx = 1.218 Mg m−3
Mo Kα radiation, λ = 0.71073 Å
Cell parameters from 2551 reflections
θ = 2.8–28.3°
µ = 0.08 mm−1
T = 100 K
Mr = 198.25
Trigonal, R3
Hall symbol: -R 3
a = 23.013 (2) Å
c = 10.6067 (11) Å
V = 4864.8 (7) Å3
Z = 18
F(000) = 1908
Block, colourless
0.40 × 0.35 × 0.30 mm
Data collection
Bruker SMART APEX CCD
diffractometer
Radiation source: fine-focus sealed tube
graphite
ω scans
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
Tmin = 0.971, Tmax = 0.978
6286 measured reflections
2475 independent reflections
2022 reflections with I > 2σ(I)
Rint = 0.026
θmax = 27.5°, θmin = 1.8°
h = −28→28
k = −29→14
l = −13→13
Refinement
Refinement on F2
Primary atom site location: structure-invariant direct
methods
Secondary atom site location: difference Fourier map
Hydrogen site location: inferred from neighbouring
sites
Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.045

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wR(F2) = 0.121
H atoms treated by a mixture of independent and
constrained refinement
w = 1/[σ2(Fo2) + (0.0533P)2 + 4.2609P]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max < 0.001
Δρmax = 0.43 e Å−3
Δρmin = −0.30 e Å−3
S = 1.08
2475 reflections
141 parameters
1 restraint
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 mat-
rix. 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, convention-
al 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)
x
0.13170 (5)
0.1201 (9)
0.20865 (7)
0.18864 (8)
0.1637
0.20471 (9)
0.1911
0.24081 (9)
0.2523
0.26018 (8)
0.2847
0.24463 (7)
0.26458 (8)
0.2878
0.2244
0.2946
0.18897 (6)
0.2264
0.17524 (6)
0.22851 (7)
0.2733
0.21660 (7)
0.2533
0.15144 (7)
0.1433
y
0.08915 (5)
0.0483 (5)
0.19098 (7)
0.21209 (7)
0.1808
0.27864 (8)
0.2930
0.32372 (8)
0.3694
0.30288 (8)
0.3344
0.23669 (7)
0.21578 (9)
0.2545
0.1806
0.1984
0.11780 (6)
0.1162
0.07865 (6)
0.08429 (7)
0.1148
0.04561 (7)
0.0500
0.00071 (7)
−0.0263
z
0.01453 (9)
0.0010 (18)
0.11187 (14)
0.21715 (15)
0.2816
0.22928 (18)
0.3018
0.1346 (2)
0.1423
0.0295 (2)
−0.0349
0.01529 (16)
−0.10289 (17)
−0.1591
−0.1450
−0.0819
0.09612 (12)
0.0515
0.21775 (12)
0.28925 (13)
0.2642
0.39708 (14)
0.4457
0.43395 (13)
0.5069
Uiso*/Ueq
0.0229 (2)
0.043 (5)*
0.0237 (3)
0.0306 (3)
0.037*
0.0417 (4)
0.050*
0.0495 (5)
0.059*
0.0433 (5)
0.052*
0.0321 (4)
0.0422 (4)
0.063*
0.063*
0.063*
0.0206 (3)
0.025*
0.0183 (3)
0.0247 (3)
0.030*
0.0276 (3)
0.033*
0.0247 (3)
0.030*
O1
H1
C1
C2
H2
C3
H3
C4
H4
C5
H5
C6
C7
H7A
H7B
H7C
C8
H8
C9
C10
H10
C11
H11
C12
H12

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C13
H13
C14
H14
0.09838 (7)
0.0536
0.11032 (7)
0.0735
−0.00461 (7)
−0.0350
0.03426 (6)
0.0304
0.36404 (13)
0.3894
0.25682 (13)
0.2095
0.0229 (3)
0.027*
0.0207 (3)
0.025*
Atomic displacement parameters (Å2)
U11
0.0260 (5)
0.0180 (6)
0.0317 (8)
0.0449 (10)
0.0386 (10)
0.0261 (8)
0.0162 (6)
0.0275 (8)
0.0190 (6)
0.0205 (6)
0.0188 (6)
0.0246 (7)
0.0301 (7)
0.0220 (7)
0.0193 (6)
U22
0.0200 (5)
0.0186 (6)
0.0235 (7)
0.0297 (8)
0.0164 (7)
0.0226 (8)
0.0257 (7)
0.0477 (10)
0.0213 (6)
0.0158 (6)
0.0233 (7)
0.0302 (8)
0.0228 (7)
0.0217 (6)
0.0218 (6)
U33
0.0247 (5)
0.0340 (8)
0.0397 (9)
0.0577 (11)
0.0895 (15)
0.0717 (13)
0.0487 (10)
0.0491 (10)
0.0239 (7)
0.0209 (6)
0.0301 (7)
0.0289 (8)
0.0234 (7)
0.0237 (7)
0.0230 (7)
U12
0.0130 (4)
0.0087 (5)
0.0161 (6)
0.0241 (8)
0.0106 (7)
0.0051 (6)
0.0062 (6)
0.0171 (8)
0.0118 (5)
0.0107 (5)
0.0091 (5)
0.0144 (6)
0.0148 (6)
0.0100 (5)
0.0118 (5)
U13
−0.0060 (4)
−0.0060 (5)
−0.0096 (6)
−0.0221 (8)
−0.0297 (10)
−0.0108 (8)
−0.0050 (6)
0.0090 (7)
−0.0006 (5)
−0.0001 (5)
−0.0017 (5)
−0.0055 (6)
−0.0001 (5)
0.0020 (5)
−0.0014 (5)
U23
−0.0017 (4)
0.0017 (5)
−0.0041 (6)
−0.0149 (8)
−0.0038 (8)
0.0127 (8)
0.0106 (7)
0.0230 (8)
0.0022 (5)
−0.0007 (5)
0.0023 (5)
0.0027 (6)
0.0027 (5)
−0.0008 (5)
−0.0016 (5)
O1
C1
C2
C3
C4
C5
C6
C7
C8
C9
C10
C11
C12
C13
C14
Geometric parameters (Å, °)
O1—C8
O1—H1
C1—C2
C1—C6
C1—C8
C2—C3
C2—H2
C3—C4
C3—H3
C4—C5
C4—H4
C5—C6
C5—H5
C6—C7
C7—H7A
1.4323 (16)
0.852 (9)
1.385 (2)
1.404 (2)
1.5188 (18)
1.390 (2)
0.9500
1.383 (3)
0.9500
1.373 (3)
0.9500
1.388 (2)
0.9500
1.495 (3)
0.9800
C7—H7B
C7—H7C
C8—C9
C8—H8
C9—C14
C9—C10
C10—C11
C10—H10
C11—C12
C11—H11
C12—C13
C12—H12
C13—C14
C13—H13
C14—H14
0.9800
0.9800
1.5137 (18)
1.0000
1.3862 (18)
1.3911 (18)
1.390 (2)
0.9500
1.386 (2)
0.9500
1.3806 (19)
0.9500
1.3868 (19)
0.9500
0.9500
C8—O1—H1
C2—C1—C6
C2—C1—C8
C6—C1—C8
C1—C2—C3
C1—C2—H2
C3—C2—H2
108.5 (13)
120.03 (13)
120.69 (13)
119.20 (13)
120.59 (16)
119.7
119.7
O1—C8—C9
O1—C8—C1
C9—C8—C1
O1—C8—H8
C9—C8—H8
C1—C8—H8
C14—C9—C10
111.77 (10)
105.81 (10)
115.10 (11)
108.0
108.0
108.0
118.73 (12)

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C4—C3—C2
C4—C3—H3
C2—C3—H3
C5—C4—C3
C5—C4—H4
C3—C4—H4
C4—C5—C6
C4—C5—H5
C6—C5—H5
C5—C6—C1
C5—C6—C7
C1—C6—C7
C6—C7—H7A
C6—C7—H7B
H7A—C7—H7B
C6—C7—H7C
H7A—C7—H7C
H7B—C7—H7C
119.23 (18)
120.4
120.4
120.38 (15)
119.8
119.8
121.39 (17)
119.3
119.3
118.37 (16)
119.48 (15)
122.12 (14)
109.5
109.5
109.5
109.5
109.5
109.5
C14—C9—C8
C10—C9—C8
C11—C10—C9
C11—C10—H10
C9—C10—H10
C12—C11—C10
C12—C11—H11
C10—C11—H11
C13—C12—C11
C13—C12—H12
C11—C12—H12
C12—C13—C14
C12—C13—H13
C14—C13—H13
C9—C14—C13
C9—C14—H14
C13—C14—H14
121.37 (12)
119.81 (11)
120.43 (13)
119.8
119.8
120.20 (13)
119.9
119.9
119.60 (13)
120.2
120.2
120.14 (13)
119.9
119.9
120.89 (12)
119.6
119.6
C6—C1—C2—C3
C8—C1—C2—C3
C1—C2—C3—C4
C2—C3—C4—C5
C3—C4—C5—C6
C4—C5—C6—C1
C4—C5—C6—C7
C2—C1—C6—C5
C8—C1—C6—C5
C2—C1—C6—C7
C8—C1—C6—C7
C2—C1—C8—O1
C6—C1—C8—O1
C2—C1—C8—C9
−1.0 (2)
−177.73 (13)
0.3 (2)
0.4 (2)
−0.3 (2)
−0.4 (2)
177.76 (15)
1.0 (2)
177.84 (13)
−177.07 (14)
−0.3 (2)
98.25 (14)
−78.54 (14)
−25.70 (17)
C6—C1—C8—C9
O1—C8—C9—C14
C1—C8—C9—C14
O1—C8—C9—C10
C1—C8—C9—C10
C14—C9—C10—C11
C8—C9—C10—C11
C9—C10—C11—C12
C10—C11—C12—C13
C11—C12—C13—C14
C10—C9—C14—C13
C8—C9—C14—C13
C12—C13—C14—C9
157.52 (12)
−17.47 (17)
103.27 (14)
159.14 (12)
−80.12 (15)
0.6 (2)
−176.11 (12)
0.4 (2)
−1.0 (2)
0.7 (2)
−0.92 (19)
175.72 (12)
0.3 (2)
Hydrogen-bond geometry (Å, °)
D—H···A
O1—H1···O1i
Symmetry codes: (i) y, −x+y, −z.
D—HH···AD···AD—H···A
0.85 (1)1.85 (1) 2.6967 (10)174.(2)

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Fig. 1

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Fig. 2

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Fig. 3