[Journal logo]

Volume 69 
Part 1 
Page o126  
January 2013  

Received 23 November 2012
Accepted 16 December 2012
Online 22 December 2012

Key indicators
Single-crystal X-ray study
T = 190 K
Mean [sigma](C-C) = 0.002 Å
R = 0.043
wR = 0.123
Data-to-parameter ratio = 14.7
Details
Open access

Triclinic polymorph of 4-[4-(4-formylphenoxy)butoxy]benzaldehyde

aDepartment of Chemistry, J. J. Strossmayer University, Osijek, Franje Kuhaca 20, HR-31000 Osijek, Croatia
Correspondence e-mail: tombalic@kemija.unios.hr

The title compound, C18H18O4, is a triclinic polymorph of the previously reported monoclinic polymorph [Han & Zhen (2005[Han, J.-R. & Zhen, X.-L. (2005). Acta Cryst. E61, o4358-o4359.]). Acta Cryst. E61, o4358-o4359]. In the crystal of the triclinic polymorph, molecules are linked by two pairs of C-H...O hydrogen bonds, forming a two-dimensional network parallel to (102), and enclosing loops with graph set motifs of R22(8) and R22(6).

Related literature

For the monoclinic polymorph, see: Han & Zhen (2005[Han, J.-R. & Zhen, X.-L. (2005). Acta Cryst. E61, o4358-o4359.]). For related structures and the synthesis of similar compounds, see: Balic et al. (2012[Balic, T., Markovic, B. & Balic, I. (2012). Acta Cryst. E68, o2664.]); Ma & Cao (2011[Ma, Z. & Cao, Y. (2011). Acta Cryst. E67, o1503.]); Dehno Khalaji et al. (2011[Dehno Khalaji, A., Hafez Ghoran, S., Gotoh, K. & Ishida, H. (2011). Acta Cryst. E67, o2484.]); Narasimha Moorthy et al. (2005[Narasimha Moorthy, J., Natarajan, R. & Venugopalan, P. (2005). J. Mol. Struct. 741, 107-114.]); Ilhan et al. (2007[Ilhan, S., Temel, H., Yilmaz, I. & Kilic, A. (2007). Transition Met. Chem. 32, 344-349.]). For graph-set analysis of hydrogen bonds, see Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C18H18O4

  • Mr = 298.32

  • Triclinic, [P \overline 1]

  • a = 4.4969 (2) Å

  • b = 7.9507 (6) Å

  • c = 11.0679 (8) Å

  • [alpha] = 73.854 (6)°

  • [beta] = 84.788 (5)°

  • [gamma] = 80.903 (5)°

  • V = 374.86 (4) Å3

  • Z = 1

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 190 K

  • 0.59 × 0.35 × 0.21 mm

Data collection
  • Oxford Diffraction Xcalibur Sapphire3 diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.683, Tmax = 1.000

  • 2235 measured reflections

  • 1473 independent reflections

  • 1272 reflections with I > 2[sigma](I)

  • Rint = 0.010

Refinement
  • R[F2 > 2[sigma](F2)] = 0.043

  • wR(F2) = 0.123

  • S = 1.04

  • 1473 reflections

  • 100 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.29 e Å-3

  • [Delta][rho]min = -0.17 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C6-H6...O2i 0.95 2.58 3.4985 (16) 162
C1-H1...O1ii 0.95 2.59 3.3953 (18) 143
Symmetry codes: (i) -x+2, -y, -z+1; (ii) -x, -y-1, -z+2.

Data collection: CrysAlis PRO (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR2004 (Burla et al., 2005[Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381-388.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]), PARST97 (Nardelli, 1995[Nardelli, M. (1995). J. Appl. Cryst. 28, 659.]) 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.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NG5308 ).


Acknowledgements

This work was supported by the Ministry of Science, Education and Sports of the Republic of Croatia (grant No. 119-1193079-1084). The authors wish to thank Professor Dubravka Matkovic-Calogovic for help with the crystallography.

References

Balic, T., Markovic, B. & Balic, I. (2012). Acta Cryst. E68, o2664.  [CrossRef] [details]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381-388.  [ISI] [CrossRef] [ChemPort] [details]
Dehno Khalaji, A., Hafez Ghoran, S., Gotoh, K. & Ishida, H. (2011). Acta Cryst. E67, o2484.  [CSD] [CrossRef] [details]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Han, J.-R. & Zhen, X.-L. (2005). Acta Cryst. E61, o4358-o4359.  [CSD] [CrossRef] [details]
Ilhan, S., Temel, H., Yilmaz, I. & Kilic, A. (2007). Transition Met. Chem. 32, 344-349.  [ISI] [CrossRef] [ChemPort]
Ma, Z. & Cao, Y. (2011). Acta Cryst. E67, o1503.  [CSD] [CrossRef] [details]
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.  [ISI] [CrossRef] [ChemPort] [details]
Narasimha Moorthy, J., Natarajan, R. & Venugopalan, P. (2005). J. Mol. Struct. 741, 107-114.  [ISI] [CSD] [CrossRef]
Nardelli, M. (1995). J. Appl. Cryst. 28, 659.  [CrossRef] [details]
Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2013). E69, o126  [ doi:10.1107/S1600536812050994 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.