4-(4-Octyloxybenzo­yloxy)benzoic acid

Muhammad, K.; Khawar Rauf, M.; Ebihara, M.; Hameed, S.

doi:10.1107/S1600536809003298

Volume 65
Part 2
Page o424
February 2009

Received 22 January 2009
Accepted 27 January 2009
Online 31 January 2009

Key indicators
Single-crystal X-ray study
T = 123 K
Mean (C-C) = 0.003 Å
R = 0.081
wR = 0.138
Data-to-parameter ratio = 17.6
Details

4-(4-Octyloxybenzoyloxy)benzoic acid

Khushi Muhammad,^a M. Khawar Rauf,^a Masahiro Ebihara ^b and Shahid Hameed ^a ^*

^aDepartment of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan, and ^bDepartment of Chemistry, Faculty of Engineering, Gifu University, Yanagido, Gifu 501-1193, Japan
Correspondence e-mail: shameed@qau.edu.pk

The title compound, C₂₂H₂₆O₅, is an important intermediate for the synthesis of side-chain ligands for polymeric liquid crystals. The octyl group is coplanar with the central C₆O moiety, where the maximum deviation of a C atom in the octyl group from the C₆O plane is 0.161 (5) Å. The crystal structure is stabilized by intermolecular O-HO hydrogen bonds.

Related literature

For studies of aromatic carboxylic acids and their applications, see: Naoum et al. (2008); Nazir et al. (2008a,b); Gabert et al. (2006); Aranzazu et al. (2006); Hussain et al. (2005); Shafiq et al. (2005); Ahmad et al. (2003); Ribeiro et al. (2008); Hameed & Rama (2004); For related structures, see: Muhammad et al. (2008); Hartung et al. (1997)

Experimental

Crystal data

C₂₂H₂₆O₅
M_r = 370.43
Monoclinic, P 2₁ /n
a = 13.528 (8) Å
b = 7.245 (4) Å
c = 20.903 (12) Å
= 111.407 (8)°
V = 1907.5 (18) Å³
Z = 4
Mo K radiation
= 0.09 mm^-1
T = 123 K
0.40 × 0.30 × 0.15 mm

Data collection

Rigaku/MSC Mercury CCD diffractometer
Absorption correction: none
14669 measured reflections
4358 independent reflections
3870 reflections with I > 2(I)
R_int = 0.048

Refinement

R[F² > 2(F²)] = 0.081
wR(F²) = 0.138
S = 1.31
4358 reflections
247 parameters
H-atom parameters constrained
_max = 0.28 e Å^-3
_min = -0.19 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O3-H3OO4ⁱ	0.84	1.85	2.659 (3)	161
O4-H4OO3ⁱ	0.84	1.83	2.659 (3)	171
Symmetry code: (i) -x+2, -y+1, -z+1.

Data collection: CrystalClear (Molecular Structure Corporation & Rigaku, 2001); cell refinement: CrystalClear; data reduction: TEXSAN (Molecular Structure Corporation & Rigaku, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97 and TEXSAN.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG2473 ).

Acknowledgements

MKR is grateful to the Higher Education Commission of Pakistan for financial support under the International Support Initiative Programme for a doctoral fellowship at Gifu University, Japan.

References

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organic compounds