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Volume 69 
Part 7 
Page o1149  
July 2013  

Received 6 May 2013
Accepted 12 June 2013
Online 26 June 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.005 Å
R = 0.036
wR = 0.074
Data-to-parameter ratio = 19.5
Details
Open access

1,6-Dibromonaphthalen-2-ol methanol monosolvate

aDepartment of Chemistry, The College of New Jersey, 2000 Pennington Rd, Ewing, NJ 08628, USA
Correspondence e-mail: chan@tcnj.edu

The naphthol-containing molecule of the title compound, C10H6Br2O·CH3OH, crystallized as a methanol monosolvate and is planar to within 0.069 (1) Å for all non-H atoms. In the crystal, molecules are linked by two pairs of O-H...O hydrogen bonds, involving the methanol molecule, forming dimer-like arrangements. The crystal structure is further stabilized by [pi]-[pi] stacking [centroid-centroid distance = 3.676 (2) Å] and Br...Br interactions [3.480 (4) and 3.786 (1) Å], forming a three-dimensional structure.

Related literature

For information on applications of 1,6-dibromo-2-napthol, see: Costa et al. (2012[Costa, B., Irvine, M., Fang, G., Eaves, R., Mayo-Martin, M., Laube, B., Jane, D. & Monaghan, D. (2012). Neuropharmacology, 62, 1730-1736.]); Takeuchi et al. (2000[Takeuchi, Y., Shibata, T. & Shirakami, T. (2000). Jpn. Kokai Tokkyo Koho, 9, 99-105.]); Kalra & Kumar (2005[Kalra, B. & Kumar, A. (2005). US Patent Appl. Publ. 14.]). For related structures, see: Rozycka-Sokolowska & Marciniak (2009[Rozycka-Sokolowska, E. & Marciniak, B. (2009). Acta Cryst. C65, o207-o210.]). For halogen-halogen interactions, see: Zordan & Brammer (2006[Zordan, F. & Brammer, L. (2006). Cryst. Growth Des. 6, 1374-1379.]); Schlueter et al. (2012[Schlueter, J., Park, H., Halder, G., Armand, W., Dunmars, C., Chapman, K., Manson, J., Singleton, J., McDonald, R., Plonczak, A., Kang, J., Lee, C., Whangbo, M., Lancaster, T., Steele, A., Franke, I., Wright, J., Blundell, S., Pratt, F., deGeorge, J., Turnbull, M. & Landee, C. (2012). Inorg. Chem. 51, 2121-2129.]); Desiraju & Parthasarathy (1989[Desiraju, G. & Parthasarathy, R. (1989). J. Am. Chem. Soc. 111, 8725-8726.]).

[Scheme 1]

Experimental

Crystal data
  • C10H6Br2O·CH4O

  • Mr = 334.01

  • Monoclinic, P 21 /n

  • a = 3.9971 (4) Å

  • b = 12.4705 (12) Å

  • c = 22.462 (2) Å

  • [beta] = 92.442 (1)°

  • V = 1118.62 (19) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 7.22 mm-1

  • T = 100 K

  • 0.26 × 0.11 × 0.01 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2011[Bruker (2011). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.521, Tmax = 0.746

  • 12658 measured reflections

  • 2690 independent reflections

  • 2082 reflections with I > 2[sigma](I)

  • Rint = 0.057

Refinement
  • R[F2 > 2[sigma](F2)] = 0.036

  • wR(F2) = 0.074

  • S = 1.02

  • 2690 reflections

  • 138 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 1.31 e Å-3

  • [Delta][rho]min = -0.60 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...O2i 0.84 1.80 2.632 (4) 171
O2-H2...O1ii 0.84 2.01 2.809 (4) 159
Symmetry codes: (i) x+1, y, z; (ii) -x+1, -y+1, -z+2.

Data collection: APEX2 (Bruker, 2011[Bruker (2011). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2011[Bruker (2011). APEX2, SAINT and SADABS. 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: CrystalMaker (CrystalMaker Software, 2009[CrystalMaker Software (2009). CrystalMaker for Windows. CrystalMaker Software Ltd, Oxford, England.]); software used to prepare material for publication: enCIFer (Allen et al., 2004[Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, M. (2004). J. Appl. Cryst. 37, 335-338.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2599 ).


Acknowledgements

The authors gratefully acknowledge The College of New Jersey's School of Science for research funding and the National Science Foundation for major research instrumentation grant (NSF-0922931) for diffractometer acquisition.

References

Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, M. (2004). J. Appl. Cryst. 37, 335-338.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Bruker (2011). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Costa, B., Irvine, M., Fang, G., Eaves, R., Mayo-Martin, M., Laube, B., Jane, D. & Monaghan, D. (2012). Neuropharmacology, 62, 1730-1736.  [Web of Science] [CrossRef] [ChemPort] [PubMed]
CrystalMaker Software (2009). CrystalMaker for Windows. CrystalMaker Software Ltd, Oxford, England.
Desiraju, G. & Parthasarathy, R. (1989). J. Am. Chem. Soc. 111, 8725-8726.  [CrossRef] [ChemPort] [Web of Science]
Kalra, B. & Kumar, A. (2005). US Patent Appl. Publ. 14.
Rozycka-Sokolowska, E. & Marciniak, B. (2009). Acta Cryst. C65, o207-o210.  [CrossRef] [ChemPort] [IUCr Journals]
Schlueter, J., Park, H., Halder, G., Armand, W., Dunmars, C., Chapman, K., Manson, J., Singleton, J., McDonald, R., Plonczak, A., Kang, J., Lee, C., Whangbo, M., Lancaster, T., Steele, A., Franke, I., Wright, J., Blundell, S., Pratt, F., deGeorge, J., Turnbull, M. & Landee, C. (2012). Inorg. Chem. 51, 2121-2129.  [Web of Science] [CSD] [CrossRef] [ChemPort] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Takeuchi, Y., Shibata, T. & Shirakami, T. (2000). Jpn. Kokai Tokkyo Koho, 9, 99-105.
Zordan, F. & Brammer, L. (2006). Cryst. Growth Des. 6, 1374-1379.  [CSD] [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o1149  [ doi:10.1107/S1600536813016371 ]

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