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

Balić, T.; Marković, B.; Balić, I.

doi:10.1107/S1600536812050994

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 (C-C) = 0.002 Å
R = 0.043
wR = 0.123
Data-to-parameter ratio = 14.7
Details

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

Tomislav Balic,^a ^* Berislav Markovic ^a and Ivana Balic ^a

^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). Acta Cryst. E61, o4358-o4359]. In the crystal of the triclinic polymorph, molecules are linked by two pairs of C-HO 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). For related structures and the synthesis of similar compounds, see: Balic et al. (2012); Ma & Cao (2011); Dehno Khalaji et al. (2011); Narasimha Moorthy et al. (2005); Ilhan et al. (2007). For graph-set analysis of hydrogen bonds, see Bernstein et al. (1995).

Experimental

Crystal data

C₁₈H₁₈O₄
M_r = 298.32
Triclinic, $[P \overline 1]$
a = 4.4969 (2) Å
b = 7.9507 (6) Å
c = 11.0679 (8) Å
= 73.854 (6)°
= 84.788 (5)°
= 80.903 (5)°
V = 374.86 (4) Å³
Z = 1
Mo K radiation
= 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 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.683, T_max = 1.000
2235 measured reflections
1473 independent reflections
1272 reflections with I > 2(I)
R_int = 0.010

Refinement

R[F² > 2(F²)] = 0.043
wR(F²) = 0.123
S = 1.04
1473 reflections
100 parameters
H-atom parameters constrained
_max = 0.29 e Å^-3
_min = -0.17 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C6-H6O2ⁱ	0.95	2.58	3.4985 (16)	162
C1-H1O1ⁱⁱ	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); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012), PARST97 (Nardelli, 1995) and Mercury (Macrae et al., 2006).

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.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
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.
Dehno Khalaji, A., Hafez Ghoran, S., Gotoh, K. & Ishida, H. (2011). Acta Cryst. E67, o2484.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Han, J.-R. & Zhen, X.-L. (2005). Acta Cryst. E61, o4358-o4359.
Ilhan, S., Temel, H., Yilmaz, I. & Kilic, A. (2007). Transition Met. Chem. 32, 344-349.
Ma, Z. & Cao, Y. (2011). Acta Cryst. E67, o1503.
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.
Narasimha Moorthy, J., Natarajan, R. & Venugopalan, P. (2005). J. Mol. Struct. 741, 107-114.
Nardelli, M. (1995). J. Appl. Cryst. 28, 659.
Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds