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

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.

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 related diphenyl­methanol structures, see: Ferguson et al. (1995 ▶).

Experimental

Crystal data

C14H14O

M = 198.25

Trigonal,

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 ▶) 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 ▶); 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, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

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

C14H14O	Dx = 1.218 Mg m−3
Mr = 198.25	Mo Kα radiation, λ = 0.71073 Å
Trigonal, R3	Cell parameters from 2551 reflections
Hall symbol: -R 3	θ = 2.8–28.3°
a = 23.013 (2) Å	µ = 0.08 mm−1
c = 10.6067 (11) Å	T = 100 K
V = 4864.8 (7) Å3	Block, colourless
Z = 18	0.40 × 0.35 × 0.30 mm
F(000) = 1908

Bruker SMART APEX CCD diffractometer	2475 independent reflections
Radiation source: fine-focus sealed tube	2022 reflections with I > 2σ(I)
graphite	Rint = 0.026
ω scans	θmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −28→28
Tmin = 0.971, Tmax = 0.978	k = −29→14
6286 measured reflections	l = −13→13

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121	H 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 parameters	Δρmax = 0.43 e Å−3
1 restraint	Δρmin = −0.30 e Å−3

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.

	x	y	z	Uiso*/Ueq
O1	0.13170 (5)	0.08915 (5)	0.01453 (9)	0.0229 (2)
H1	0.1201 (9)	0.0483 (5)	0.0010 (18)	0.043 (5)*
C1	0.20865 (7)	0.19098 (7)	0.11187 (14)	0.0237 (3)
C2	0.18864 (8)	0.21209 (7)	0.21715 (15)	0.0306 (3)
H2	0.1637	0.1808	0.2816	0.037*
C3	0.20471 (9)	0.27864 (8)	0.22928 (18)	0.0417 (4)
H3	0.1911	0.2930	0.3018	0.050*
C4	0.24081 (9)	0.32372 (8)	0.1346 (2)	0.0495 (5)
H4	0.2523	0.3694	0.1423	0.059*
C5	0.26018 (8)	0.30288 (8)	0.0295 (2)	0.0433 (5)
H5	0.2847	0.3344	−0.0349	0.052*
C6	0.24463 (7)	0.23669 (7)	0.01529 (16)	0.0321 (4)
C7	0.26458 (8)	0.21578 (9)	−0.10289 (17)	0.0422 (4)
H7A	0.2878	0.2545	−0.1591	0.063*
H7B	0.2244	0.1806	−0.1450	0.063*
H7C	0.2946	0.1984	−0.0819	0.063*
C8	0.18897 (6)	0.11780 (6)	0.09612 (12)	0.0206 (3)
H8	0.2264	0.1162	0.0515	0.025*
C9	0.17524 (6)	0.07865 (6)	0.21775 (12)	0.0183 (3)
C10	0.22851 (7)	0.08429 (7)	0.28925 (13)	0.0247 (3)
H10	0.2733	0.1148	0.2642	0.030*
C11	0.21660 (7)	0.04561 (7)	0.39708 (14)	0.0276 (3)
H11	0.2533	0.0500	0.4457	0.033*
C12	0.15144 (7)	0.00071 (7)	0.43395 (13)	0.0247 (3)
H12	0.1433	−0.0263	0.5069	0.030*
C13	0.09838 (7)	−0.00461 (7)	0.36404 (13)	0.0229 (3)
H13	0.0536	−0.0350	0.3894	0.027*
C14	0.11032 (7)	0.03426 (6)	0.25682 (13)	0.0207 (3)
H14	0.0735	0.0304	0.2095	0.025*

	U11	U22	U33	U12	U13	U23
O1	0.0260 (5)	0.0200 (5)	0.0247 (5)	0.0130 (4)	−0.0060 (4)	−0.0017 (4)
C1	0.0180 (6)	0.0186 (6)	0.0340 (8)	0.0087 (5)	−0.0060 (5)	0.0017 (5)
C2	0.0317 (8)	0.0235 (7)	0.0397 (9)	0.0161 (6)	−0.0096 (6)	−0.0041 (6)
C3	0.0449 (10)	0.0297 (8)	0.0577 (11)	0.0241 (8)	−0.0221 (8)	−0.0149 (8)
C4	0.0386 (10)	0.0164 (7)	0.0895 (15)	0.0106 (7)	−0.0297 (10)	−0.0038 (8)
C5	0.0261 (8)	0.0226 (8)	0.0717 (13)	0.0051 (6)	−0.0108 (8)	0.0127 (8)
C6	0.0162 (6)	0.0257 (7)	0.0487 (10)	0.0062 (6)	−0.0050 (6)	0.0106 (7)
C7	0.0275 (8)	0.0477 (10)	0.0491 (10)	0.0171 (8)	0.0090 (7)	0.0230 (8)
C8	0.0190 (6)	0.0213 (6)	0.0239 (7)	0.0118 (5)	−0.0006 (5)	0.0022 (5)
C9	0.0205 (6)	0.0158 (6)	0.0209 (6)	0.0107 (5)	−0.0001 (5)	−0.0007 (5)
C10	0.0188 (6)	0.0233 (7)	0.0301 (7)	0.0091 (5)	−0.0017 (5)	0.0023 (5)
C11	0.0246 (7)	0.0302 (8)	0.0289 (8)	0.0144 (6)	−0.0055 (6)	0.0027 (6)
C12	0.0301 (7)	0.0228 (7)	0.0234 (7)	0.0148 (6)	−0.0001 (5)	0.0027 (5)
C13	0.0220 (7)	0.0217 (6)	0.0237 (7)	0.0100 (5)	0.0020 (5)	−0.0008 (5)
C14	0.0193 (6)	0.0218 (6)	0.0230 (7)	0.0118 (5)	−0.0014 (5)	−0.0016 (5)

O1—C8	1.4323 (16)	C7—H7B	0.9800
O1—H1	0.852 (9)	C7—H7C	0.9800
C1—C2	1.385 (2)	C8—C9	1.5137 (18)
C1—C6	1.404 (2)	C8—H8	1.0000
C1—C8	1.5188 (18)	C9—C14	1.3862 (18)
C2—C3	1.390 (2)	C9—C10	1.3911 (18)
C2—H2	0.9500	C10—C11	1.390 (2)
C3—C4	1.383 (3)	C10—H10	0.9500
C3—H3	0.9500	C11—C12	1.386 (2)
C4—C5	1.373 (3)	C11—H11	0.9500
C4—H4	0.9500	C12—C13	1.3806 (19)
C5—C6	1.388 (2)	C12—H12	0.9500
C5—H5	0.9500	C13—C14	1.3868 (19)
C6—C7	1.495 (3)	C13—H13	0.9500
C7—H7A	0.9800	C14—H14	0.9500
C8—O1—H1	108.5 (13)	O1—C8—C9	111.77 (10)
C2—C1—C6	120.03 (13)	O1—C8—C1	105.81 (10)
C2—C1—C8	120.69 (13)	C9—C8—C1	115.10 (11)
C6—C1—C8	119.20 (13)	O1—C8—H8	108.0
C1—C2—C3	120.59 (16)	C9—C8—H8	108.0
C1—C2—H2	119.7	C1—C8—H8	108.0
C3—C2—H2	119.7	C14—C9—C10	118.73 (12)
C4—C3—C2	119.23 (18)	C14—C9—C8	121.37 (12)
C4—C3—H3	120.4	C10—C9—C8	119.81 (11)
C2—C3—H3	120.4	C11—C10—C9	120.43 (13)
C5—C4—C3	120.38 (15)	C11—C10—H10	119.8
C5—C4—H4	119.8	C9—C10—H10	119.8
C3—C4—H4	119.8	C12—C11—C10	120.20 (13)
C4—C5—C6	121.39 (17)	C12—C11—H11	119.9
C4—C5—H5	119.3	C10—C11—H11	119.9
C6—C5—H5	119.3	C13—C12—C11	119.60 (13)
C5—C6—C1	118.37 (16)	C13—C12—H12	120.2
C5—C6—C7	119.48 (15)	C11—C12—H12	120.2
C1—C6—C7	122.12 (14)	C12—C13—C14	120.14 (13)
C6—C7—H7A	109.5	C12—C13—H13	119.9
C6—C7—H7B	109.5	C14—C13—H13	119.9
H7A—C7—H7B	109.5	C9—C14—C13	120.89 (12)
C6—C7—H7C	109.5	C9—C14—H14	119.6
H7A—C7—H7C	109.5	C13—C14—H14	119.6
H7B—C7—H7C	109.5
C6—C1—C2—C3	−1.0 (2)	C6—C1—C8—C9	157.52 (12)
C8—C1—C2—C3	−177.73 (13)	O1—C8—C9—C14	−17.47 (17)
C1—C2—C3—C4	0.3 (2)	C1—C8—C9—C14	103.27 (14)
C2—C3—C4—C5	0.4 (2)	O1—C8—C9—C10	159.14 (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—C11	0.6 (2)
C4—C5—C6—C7	177.76 (15)	C8—C9—C10—C11	−176.11 (12)
C2—C1—C6—C5	1.0 (2)	C9—C10—C11—C12	0.4 (2)
C8—C1—C6—C5	177.84 (13)	C10—C11—C12—C13	−1.0 (2)
C2—C1—C6—C7	−177.07 (14)	C11—C12—C13—C14	0.7 (2)
C8—C1—C6—C7	−0.3 (2)	C10—C9—C14—C13	−0.92 (19)
C2—C1—C8—O1	98.25 (14)	C8—C9—C14—C13	175.72 (12)
C6—C1—C8—O1	−78.54 (14)	C12—C13—C14—C9	0.3 (2)
C2—C1—C8—C9	−25.70 (17)

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)

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) .