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Volume 69 
Part 11 
Pages o1655-o1656  
November 2013  

Received 19 September 2013
Accepted 28 September 2013
Online 19 October 2013

Key indicators
Single-crystal X-ray study
T = 150 K
Mean [sigma](C-C) = 0.001 Å
R = 0.034
wR = 0.093
Data-to-parameter ratio = 15.2
Details
Open access

1,5-Di­meth­oxy­naphthalene

aDepartment of Chemistry, University of Cape Coast, Cape Coast, Ghana, and bChemical Crystallography, Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, England
Correspondence e-mail: emmanuel_jp@yahoo.com

The title compound, C12H12O2, lies across an inversion centre. The mol­ecular structure suggests that the meth­oxy groups in the 1- and 5-positions of the naphthalene moiety do not significantly distort the planar conformation of the ring system, which has a maximum deviation of 0.0025 (9) Å. In the crystal, mol­ecules pack in a herringbone arrangement in layers parallel to (100) and with chains propagating along [101] formed by very weak C-H...O inter­actions.

Related literature

For details of the uses of 1,5-di­meth­oxy­naphthalene, see: Ashton et al. (1991[Ashton, P. R., Brown, C. L., Chrystal, E. J. T., Goodnow, T. T., Kaifer, A. E., Parry, K. P., Phili, D., Slawin, A. M. Z., Spencer, N., Stoddart, J. F. & Williams, D. J. (1991). J. Chem. Soc. Chem. Commun. pp. 634-639.]); Amabilino & Veciana (2003[Amabilino, D. B. & Veciana, J. (2003). In Magnetism, Molecules to Materials II, edited by J. S. Miller & M. Drillon. New York: John Wiley & Sons, Inc.]); Kim et al. (2008[Kim, Y. K., Jeonmin-dong, Y., Daejeon, L., Hyun, S., Eoeun-dong, Y., Daejeon, R., Mun, C., Jeonmin-dong, Y., Daejeon, C., Yong, S., Banseok-dong, Y., Daejeon, S., Gyu, Y. & Galma-dong, S. (2008). Patent Number WO 2008/18645 A1.]); Kato et al. (2003[Kato, S., Suzuki, D. & Yoshiko, Y. S. (2003). US Patent No. US 6,656,328 B2, 2nd December.]); Rawson et al. (2006[Rawson, J. M., Alberola, A. & Whalley, A. (2006). J. Mater. Chem. 16, 2560-2575.]). For related compounds, see: Allen & Kirby (1984[Allen, F. H. & Kirby, A. J. (1984). J. Am. Chem. Soc. 106, 6197-6200.]); Beintema (1965[Beintema, J. (1965). Acta Cryst. 18, 647-654.]); Belskii et al. (1990[Belskii, V. K., Kharchenko, E. V., Sobolev, A. N., Zavodnik, V. E., Kolomiets, N. A., Prober, G. S. & Oleksenko, L. P. (1990). Zh. Strukt. Khim. 31, 116-121.]); Bolte & Bauch (1998[Bolte, M. & Bauch, C. (1998). Acta Cryst. C54, 1862-1863.]); Cosmo et al. (1990[Cosmo, R., Hambley, T. W. & Sternhell, S. (1990). Acta Cryst. B46, 557-562.]); Cruickshank (1957[Cruickshank, D. W. J. (1957). Acta Cryst. 10, 504-508.]); Gaultier & Hauw (1967[Gaultier, J. & Hauw, C. (1967). Acta Cryst. 23, 1016-1024.]); Pawley & Yeats (1969[Pawley, G. S. & Yeats, E. A. (1969). Acta Cryst. B25, 2009-2013.]); Rozycka-Sokolowska & Marciniak (2009[Rozycka-Sokolowska, E. & Marciniak, B. (2009). Acta Cryst. C65, o565-o568.]); Rozycka-Sokolowska et al. (2004[Rozycka-Sokolowska, E., Marciniak, B. & Pavlyuk, V. (2004). Acta Cryst. E60, o884-o885.], 2005[Rozycka-Sokolowska, E., Marciniak, B. & Pavlyuk, V. (2005). Acta Cryst. E61, o114-o115.]); Wiedenfeld et al. (1999[Wiedenfeld, D., Xiao, W. & Gravelle, P. W. (1999). J. Chem. Crystallogr. 29, 955-959.]); Wilson et al. (1996[Wilson, C. C., Shankland, N. & Florence, A. J. (1996). Chem. Phys. Lett. 253, 103-107.]); Wilson (1997[Wilson, C. C. (1997). Chem Commun. pp. 1281-1282.]). For details of the low-temperature device used, see: Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]). For details of the H-atom treatment, see: Cooper et al. (2010[Cooper, R. I., Thompson, A. L. & Watkin, D. J. (2010). J. Appl. Cryst. 43, 1100-1107.]). For Cambridge Structural Database, see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]).

[Scheme 1]

Experimental

Crystal data
  • C12H12O2

  • Mr = 188.23

  • Monoclinic, P 21 /c

  • a = 7.0412 (3) Å

  • b = 10.1058 (4) Å

  • c = 6.5773 (2) Å

  • [beta] = 95.509 (3)°

  • V = 465.86 (3) Å3

  • Z = 2

  • Cu K[alpha] radiation

  • [mu] = 0.73 mm-1

  • T = 150 K

  • 0.18 × 0.08 × 0.01 mm

Data collection
  • Oxford Diffraction SuperNova diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007[Oxford Diffraction (2007). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]) Tmin = 0.59, Tmax = 1.00

  • 7624 measured reflections

  • 975 independent reflections

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

  • Rint = 0.027

Refinement
  • R[F2 > 2[sigma](F2)] = 0.034

  • wR(F2) = 0.093

  • S = 1.00

  • 971 reflections

  • 64 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.22 e Å-3

  • [Delta][rho]min = -0.18 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C7-H73...O6i 0.98 2.70 3.495 (1) 139
Symmetry code: (i) -x, -y+1, -z+1.

Data collection: SUPERNOVA (Oxford Diffraction, 2007[Oxford Diffraction (2007). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]); cell refinement: CrysAlis PRO (Oxford Diffraction, 2007[Oxford Diffraction (2007). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]); data reduction: CrysAlis PRO; 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: CRYSTALS (Betteridge et al., 2003[Betteridge, P. W., Carruthers, J. R., Cooper, R. I., Prout, K. & Watkin, D. J. (2003). J. Appl. Cryst. 36, 1487.]); molecular graphics: CAMERON (Watkin et al., 1996[Watkin, D. J., Prout, C. K. & Pearce, L. J. (1996). CAMERON. Chemical Crystallography Laboratory, Oxford, England.]); software used to prepare material for publication: CRYSTALS.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5655 ).


Acknowledgements

EMO would like to thank the University of Cape Coast for assistance with travel and the Department of Chemistry, University of Oxford, for support.

References

Allen, F. H. (2002). Acta Cryst. B58, 380-388.  [Web of Science] [CrossRef] [IUCr Journals]
Allen, F. H. & Kirby, A. J. (1984). J. Am. Chem. Soc. 106, 6197-6200.  [CrossRef] [ChemPort] [Web of Science]
Amabilino, D. B. & Veciana, J. (2003). In Magnetism, Molecules to Materials II, edited by J. S. Miller & M. Drillon. New York: John Wiley & Sons, Inc.
Ashton, P. R., Brown, C. L., Chrystal, E. J. T., Goodnow, T. T., Kaifer, A. E., Parry, K. P., Phili, D., Slawin, A. M. Z., Spencer, N., Stoddart, J. F. & Williams, D. J. (1991). J. Chem. Soc. Chem. Commun. pp. 634-639.  [CrossRef] [Web of Science]
Beintema, J. (1965). Acta Cryst. 18, 647-654.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Belskii, V. K., Kharchenko, E. V., Sobolev, A. N., Zavodnik, V. E., Kolomiets, N. A., Prober, G. S. & Oleksenko, L. P. (1990). Zh. Strukt. Khim. 31, 116-121.  [ChemPort]
Betteridge, P. W., Carruthers, J. R., Cooper, R. I., Prout, K. & Watkin, D. J. (2003). J. Appl. Cryst. 36, 1487.  [Web of Science] [CrossRef] [IUCr Journals]
Bolte, M. & Bauch, C. (1998). Acta Cryst. C54, 1862-1863.  [CSD] [CrossRef] [IUCr Journals]
Cooper, R. I., Thompson, A. L. & Watkin, D. J. (2010). J. Appl. Cryst. 43, 1100-1107.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.  [CrossRef] [ChemPort] [Web of Science] [IUCr Journals]
Cosmo, R., Hambley, T. W. & Sternhell, S. (1990). Acta Cryst. B46, 557-562.  [CSD] [CrossRef] [IUCr Journals]
Cruickshank, D. W. J. (1957). Acta Cryst. 10, 504-508.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Gaultier, J. & Hauw, C. (1967). Acta Cryst. 23, 1016-1024.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Kato, S., Suzuki, D. & Yoshiko, Y. S. (2003). US Patent No. US 6,656,328 B2, 2nd December.
Kim, Y. K., Jeonmin-dong, Y., Daejeon, L., Hyun, S., Eoeun-dong, Y., Daejeon, R., Mun, C., Jeonmin-dong, Y., Daejeon, C., Yong, S., Banseok-dong, Y., Daejeon, S., Gyu, Y. & Galma-dong, S. (2008). Patent Number WO 2008/18645 A1.
Oxford Diffraction (2007). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.
Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Pawley, G. S. & Yeats, E. A. (1969). Acta Cryst. B25, 2009-2013.  [CSD] [CrossRef] [IUCr Journals]
Rawson, J. M., Alberola, A. & Whalley, A. (2006). J. Mater. Chem. 16, 2560-2575.  [Web of Science] [CrossRef] [ChemPort]
Rozycka-Sokolowska, E. & Marciniak, B. (2009). Acta Cryst. C65, o565-o568.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Rozycka-Sokolowska, E., Marciniak, B. & Pavlyuk, V. (2004). Acta Cryst. E60, o884-o885.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Rozycka-Sokolowska, E., Marciniak, B. & Pavlyuk, V. (2005). Acta Cryst. E61, o114-o115.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Watkin, D. J., Prout, C. K. & Pearce, L. J. (1996). CAMERON. Chemical Crystallography Laboratory, Oxford, England.
Wiedenfeld, D., Xiao, W. & Gravelle, P. W. (1999). J. Chem. Crystallogr. 29, 955-959.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Wilson, C. C. (1997). Chem Commun. pp. 1281-1282.  [CSD] [CrossRef]
Wilson, C. C., Shankland, N. & Florence, A. J. (1996). Chem. Phys. Lett. 253, 103-107.  [CrossRef] [ChemPort] [Web of Science]


Acta Cryst (2013). E69, o1655-o1656   [ doi:10.1107/S1600536813026731 ]

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