2-[(2-Chloro-phen-yl)(hy-droxy)meth-yl]phenol.

In the title compound, C13H11ClO2, the dihedral angle between the mean planes of the 2-chloro-phenyl and phenol rings is 87.4 (9)°. The methyl hy-droxy group lies nearly perpendicular to the plane of its attached benzene ring [O-C-C-C torsion angle = 84.3 (3)°]. The two hy-droxy groups lie on the same side of the mol-ecule and are in a slightly twisted gauche conformation [O-C-C-O torsion angle = 77.1 (8)°] to each other. In the crystal, O-H⋯O hydrogen bonds between nearby methyl-hydroxy groups form dimers in alternating pairs aligned diagonally along the b axis. A view along the c axis reveals a hexa-meric aggregate mediated by a ring of six O-H⋯O hydrogen bonds generating an R 6 (6)(12) motif 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: Betz et al. (2011 ▶); Ferguson et al. (1995 ▶); Siddaraju et al. (2010 ▶).

Experimental

Crystal data

C13H11ClO2

M = 234.67

Trigonal,

a = 23.4627 (8) Å

c = 11.3722 (4) Å

V = 5421.6 (4) Å3

Z = 18

Cu Kα radiation

μ = 2.66 mm−1

T = 173 K

0.46 × 0.38 × 0.24 mm

Data collection

Agilent Xcalibur (Eos, Gemini) diffractometer

Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012 ▶) T min = 0.517, T max = 1.000

11532 measured reflections

2364 independent reflections

2055 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.213

S = 1.07

2364 reflections

151 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.40 e Å−3

Δρmin = −0.62 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012 ▶); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007 ▶); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: OLEX2.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813018667/sj5343sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813018667/sj5343Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813018667/sj5343Isup3.cml

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

C13H11ClO2	Dx = 1.294 Mg m−3
Mr = 234.67	Cu Kα radiation, λ = 1.5418 Å
Trigonal, R3	Cell parameters from 3836 reflections
a = 23.4627 (8) Å	θ = 3.8–72.3°
c = 11.3722 (4) Å	µ = 2.66 mm−1
V = 5421.6 (4) Å3	T = 173 K
Z = 18	Irregular, colourless
F(000) = 2196	0.46 × 0.38 × 0.24 mm

Agilent Xcalibur (Eos, Gemini) diffractometer	2364 independent reflections
Radiation source: Enhance (Cu) X-ray Source	2055 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.047
Detector resolution: 16.0416 pixels mm-1	θmax = 72.5°, θmin = 3.8°
ω scans	h = −28→25
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012)	k = −22→28
Tmin = 0.517, Tmax = 1.000	l = −12→13
11532 measured reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.065	w = 1/[σ2(Fo2) + (0.1357P)2 + 8.799P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.213	(Δ/σ)max = 0.001
S = 1.07	Δρmax = 0.40 e Å−3
2364 reflections	Δρmin = −0.62 e Å−3
151 parameters	Extinction correction: SHELXL2012 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraints	Extinction coefficient: 0.00038 (12)
Primary atom site location: structure-invariant direct methods

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

	x	y	z	Uiso*/Ueq
Cl1	0.66585 (5)	0.59567 (4)	0.59620 (10)	0.0780 (4)
O1	0.64040 (8)	0.41759 (8)	0.77861 (16)	0.0393 (5)
H1	0.6760	0.4335	0.8159	0.059*
O2	0.56637 (10)	0.49236 (11)	0.91391 (16)	0.0436 (5)
H2	0.590 (2)	0.532 (2)	0.888 (4)	0.068 (12)*
C1	0.63717 (10)	0.46886 (11)	0.71725 (19)	0.0295 (5)
H1A	0.6573	0.5090	0.7683	0.035*
C2	0.56447 (11)	0.44658 (11)	0.7019 (2)	0.0310 (5)
C3	0.53051 (12)	0.45681 (12)	0.7923 (2)	0.0370 (6)
C4	0.46358 (14)	0.43543 (14)	0.7772 (3)	0.0480 (7)
H4	0.4400	0.4422	0.8384	0.058*
C5	0.43171 (13)	0.40498 (16)	0.6757 (3)	0.0541 (8)
H5	0.3865	0.3918	0.6661	0.065*
C6	0.46467 (14)	0.39338 (17)	0.5873 (3)	0.0558 (8)
H6	0.4421	0.3711	0.5177	0.067*
C7	0.53144 (13)	0.41460 (14)	0.6004 (2)	0.0446 (7)
H7	0.5544	0.4070	0.5392	0.054*
C8	0.67533 (10)	0.48591 (12)	0.6030 (2)	0.0329 (5)
C9	0.69119 (12)	0.54381 (13)	0.5431 (2)	0.0437 (7)
C10	0.73000 (15)	0.5615 (2)	0.4418 (3)	0.0679 (11)
H10	0.7409	0.6013	0.4021	0.081*
C11	0.75243 (16)	0.5216 (3)	0.3997 (3)	0.0783 (14)
H11	0.7792	0.5339	0.3312	0.094*
C12	0.73624 (15)	0.4639 (2)	0.4566 (3)	0.0695 (12)
H12	0.7513	0.4360	0.4264	0.083*
C13	0.69824 (13)	0.44599 (15)	0.5574 (2)	0.0458 (7)
H13	0.6876	0.4060	0.5961	0.055*

	U11	U22	U33	U12	U13	U23
Cl1	0.0763 (7)	0.0518 (5)	0.1047 (9)	0.0312 (4)	−0.0183 (5)	0.0120 (4)
O1	0.0278 (8)	0.0368 (9)	0.0499 (11)	0.0137 (7)	−0.0014 (7)	0.0132 (7)
O2	0.0534 (11)	0.0509 (12)	0.0340 (9)	0.0318 (10)	0.0080 (8)	−0.0075 (8)
C1	0.0277 (11)	0.0279 (10)	0.0316 (11)	0.0130 (8)	−0.0020 (8)	−0.0008 (8)
C2	0.0282 (11)	0.0317 (11)	0.0341 (11)	0.0158 (9)	0.0014 (8)	0.0026 (9)
C3	0.0403 (13)	0.0361 (12)	0.0416 (13)	0.0243 (10)	0.0078 (10)	0.0066 (10)
C4	0.0406 (14)	0.0513 (16)	0.0607 (17)	0.0294 (12)	0.0158 (12)	0.0136 (13)
C5	0.0283 (12)	0.0592 (18)	0.073 (2)	0.0208 (12)	0.0050 (12)	0.0138 (15)
C6	0.0332 (14)	0.0679 (19)	0.0545 (17)	0.0164 (13)	−0.0109 (12)	−0.0024 (14)
C7	0.0318 (12)	0.0575 (16)	0.0386 (13)	0.0179 (11)	−0.0008 (10)	−0.0053 (11)
C8	0.0229 (10)	0.0350 (12)	0.0339 (12)	0.0093 (9)	−0.0032 (8)	−0.0030 (9)
C9	0.0319 (12)	0.0434 (14)	0.0393 (13)	0.0065 (10)	−0.0076 (10)	0.0084 (10)
C10	0.0386 (15)	0.083 (2)	0.0433 (16)	0.0008 (16)	−0.0057 (13)	0.0225 (16)
C11	0.0346 (15)	0.135 (4)	0.0338 (15)	0.0182 (19)	0.0038 (12)	0.0009 (19)
C12	0.0385 (15)	0.118 (3)	0.0506 (18)	0.0378 (18)	−0.0045 (13)	−0.032 (2)
C13	0.0336 (12)	0.0563 (16)	0.0476 (14)	0.0226 (12)	−0.0031 (10)	−0.0144 (12)

Cl1—C9	1.710 (3)	C5—C6	1.376 (5)
O1—H1	0.8400	C6—H6	0.9500
O1—C1	1.425 (3)	C6—C7	1.394 (4)
O2—H2	0.87 (5)	C7—H7	0.9500
O2—C3	1.617 (3)	C8—C9	1.394 (4)
C1—H1A	1.0000	C8—C13	1.392 (4)
C1—C2	1.524 (3)	C9—C10	1.396 (4)
C1—C8	1.514 (3)	C10—H10	0.9500
C2—C3	1.393 (3)	C10—C11	1.369 (6)
C2—C7	1.383 (4)	C11—H11	0.9500
C3—C4	1.400 (4)	C11—C12	1.372 (7)
C4—H4	0.9500	C12—H12	0.9500
C4—C5	1.367 (5)	C12—C13	1.382 (4)
C5—H5	0.9500	C13—H13	0.9500
C1—O1—H1	109.5	C7—C6—H6	120.2
C3—O2—H2	99 (3)	C2—C7—C6	120.5 (3)
O1—C1—H1A	108.1	C2—C7—H7	119.7
O1—C1—C2	106.83 (17)	C6—C7—H7	119.7
O1—C1—C8	111.67 (19)	C9—C8—C1	120.8 (2)
C2—C1—H1A	108.1	C13—C8—C1	121.2 (2)
C8—C1—H1A	108.1	C13—C8—C9	118.0 (2)
C8—C1—C2	113.87 (18)	C8—C9—Cl1	120.2 (2)
C3—C2—C1	119.7 (2)	C8—C9—C10	120.6 (3)
C7—C2—C1	120.6 (2)	C10—C9—Cl1	119.2 (3)
C7—C2—C3	119.7 (2)	C9—C10—H10	119.9
C2—C3—O2	121.7 (2)	C11—C10—C9	120.1 (3)
C2—C3—C4	118.9 (2)	C11—C10—H10	119.9
C4—C3—O2	119.4 (2)	C10—C11—H11	120.1
C3—C4—H4	119.6	C10—C11—C12	119.9 (3)
C5—C4—C3	120.9 (3)	C12—C11—H11	120.1
C5—C4—H4	119.6	C11—C12—H12	119.7
C4—C5—H5	119.8	C11—C12—C13	120.6 (4)
C4—C5—C6	120.4 (2)	C13—C12—H12	119.7
C6—C5—H5	119.8	C8—C13—H13	119.6
C5—C6—H6	120.2	C12—C13—C8	120.7 (3)
C5—C6—C7	119.6 (3)	C12—C13—H13	119.6
Cl1—C9—C10—C11	178.1 (2)	C3—C2—C7—C6	0.9 (4)
O1—C1—C2—C3	84.3 (3)	C3—C4—C5—C6	1.6 (5)
O1—C1—C2—C7	−93.8 (3)	C4—C5—C6—C7	−1.8 (5)
O1—C1—C8—C9	−165.2 (2)	C5—C6—C7—C2	0.6 (5)
O1—C1—C8—C13	11.7 (3)	C7—C2—C3—O2	178.5 (2)
O2—C3—C4—C5	−179.8 (2)	C7—C2—C3—C4	−1.2 (4)
C1—C2—C3—O2	0.4 (3)	C8—C1—C2—C3	−151.9 (2)
C1—C2—C3—C4	−179.3 (2)	C8—C1—C2—C7	29.9 (3)
C1—C2—C7—C6	179.0 (3)	C8—C9—C10—C11	0.6 (4)
C1—C8—C9—Cl1	−1.7 (3)	C9—C8—C13—C12	0.8 (4)
C1—C8—C9—C10	175.8 (2)	C9—C10—C11—C12	0.6 (5)
C1—C8—C13—C12	−176.3 (2)	C10—C11—C12—C13	−1.0 (5)
C2—C1—C8—C9	73.7 (3)	C11—C12—C13—C8	0.3 (4)
C2—C1—C8—C13	−109.4 (2)	C13—C8—C9—Cl1	−178.72 (19)
C2—C3—C4—C5	0.0 (4)	C13—C8—C9—C10	−1.2 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O1i	0.84	1.84	2.656 (2)	163

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O1i	0.84	1.84	2.656 (2)	163

Symmetry code: (i) .