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Volume 69 
Part 8 
Page o1240  
August 2013  

Received 4 July 2013
Accepted 5 July 2013
Online 13 July 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.005 Å
R = 0.065
wR = 0.213
Data-to-parameter ratio = 15.7
Details
Open access

2-[(2-Chlorophenyl)(hydroxy)methyl]phenol

aDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India,bDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, and cSri Mahadeshwara Government First Grade College, (Affiliated to University of Mysore), Kollegal 571 440, India
Correspondence e-mail: jjasinski@keene.edu

In the title compound, C13H11ClO2, the dihedral angle between the mean planes of the 2-chlorophenyl and phenol rings is 87.4 (9)°. The methyl hydroxy group lies nearly perpendicular to the plane of its attached benzene ring [O-C-C-C torsion angle = 84.3 (3)°]. The two hydroxy groups lie on the same side of the molecule 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 methylhydroxy groups form dimers in alternating pairs aligned diagonally along the b axis. A view along the c axis reveals a hexameric aggregate mediated by a ring of six O-H...O hydrogen bonds generating an R66(12) motif 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: Betz et al. (2011[Betz, R., Gerber, T., Hosten, E., Siddaraju, B. P., Yathirajan, H. S. & Ramesha, A. R. (2011). Acta Cryst. E67, o3302.]); Ferguson et al. (1995[Ferguson, G., Carroll, C. D., Glidewell, C., Zakaria, C. M. & Lough, A. J. (1995). Acta Cryst. B51, 367-377.]); Siddaraju et al. (2010[Siddaraju, B. P., Yathirajan, H. S., Narayana, B., Ng, S. W. & Tiekink, E. R. T. (2010). Acta Cryst. E66, o2136.]).

[Scheme 1]

Experimental

Crystal data
  • C13H11ClO2

  • Mr = 234.67

  • Trigonal, [R \overline 3]

  • a = 23.4627 (8) Å

  • c = 11.3722 (4) Å

  • V = 5421.6 (4) Å3

  • Z = 18

  • Cu K[alpha] radiation

  • [mu] = 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[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]) Tmin = 0.517, Tmax = 1.000

  • 11532 measured reflections

  • 2364 independent reflections

  • 2055 reflections with I > 2[sigma](I)

  • Rint = 0.047

Refinement
  • R[F2 > 2[sigma](F2)] = 0.065

  • wR(F2) = 0.213

  • S = 1.07

  • 2364 reflections

  • 151 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.40 e Å-3

  • [Delta][rho]min = -0.62 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...O1i 0.84 1.84 2.656 (2) 163
Symmetry code: (i) [y+{\script{1\over 3}}, -x+y+{\script{2\over 3}}, -z+{\script{5\over 3}}].

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007[Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790.]); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]) and Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: OLEX2.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ5343 ).


Acknowledgements

GP thanks the UOM for research facilities to complete MSc dissertation work. JPJ acknowledges the NSF-MRI program (grant No. CHE-1039027) for funds to purchase the X-ray diffractometer.

References

Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.
Betz, R., Gerber, T., Hosten, E., Siddaraju, B. P., Yathirajan, H. S. & Ramesha, A. R. (2011). Acta Cryst. E67, o3302.  [CSD] [CrossRef] [IUCr Journals]
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Ferguson, G., Carroll, C. D., Glidewell, C., Zakaria, C. M. & Lough, A. J. (1995). Acta Cryst. B51, 367-377.  [CrossRef] [Web of Science] [IUCr Journals]
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Meguro, K., Aizawa, M., Sohda, T., Kawamatsu, Y. & Nagaoka, A. (1985). Chem. Pharm. Bull. 33, 3787-3797.  [CrossRef] [ChemPort] [PubMed]
Ohkuma, T., Koizumi, M., Ikehira, H., Yokozawa, T. & Noyori, R. (2000). Org. Lett. 2, 659-662.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Siddaraju, B. P., Yathirajan, H. S., Narayana, B., Ng, S. W. & Tiekink, E. R. T. (2010). Acta Cryst. E66, o2136.  [CSD] [CrossRef] [IUCr Journals]


Acta Cryst (2013). E69, o1240  [ doi:10.1107/S1600536813018667 ]

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