2-(4-Isopropyl­benzylidene)propanoic acid

Muhammad, N.; Tahir, M.N.; Ali, S.; Zia-ur-Rehman; Kashmiri, M.A.

doi:10.1107/S1600536808020801

Volume 64
Part 8
Page o1456
August 2008

Received 21 April 2008
Accepted 4 July 2008
Online 12 July 2008

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.004 Å
R = 0.054
wR = 0.158
Data-to-parameter ratio = 20.7
Details

2-(4-Isopropylbenzylidene)propanoic acid

Niaz Muhammad,^a M. Nawaz Tahir,^b ^* Saqib Ali,^a Zia-ur-Rehman ^a and Muhammad Akram Kashmiri ^c

^aDepartment of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan,^bDepartment of Physics, University of Sargodha, Sagrodha, Pakistan, and ^cDepartment of Chemistry, Government College University, Lahore, Pakistan
Correspondence e-mail: dmntahir_uos@yahoo.com

The two molecules in the asymmetric unit of the title compound, C₁₃H₁₆O₂, form dimers through O-HO hydrogen bonding, resulting in R₂²(8) rings. Each carboxyl O atom is involved in interamolecular C-HO hydrogen bonds, forming five-membered rings. There exist dissimilar dihedral angles within the two molecules, for example the carboxylate and isopropyl groups make dihedral angles of 59.6 (4) and 71.7 (3)° in the two molecules. There are no intermolecular [pi] interactions.

Related literature

For related literature, see: Burt (2004); Hertog et al. (1995); Ma & Hayes (2004); Muhammad et al. (2007).

Experimental

Crystal data

C₁₃H₁₆O₂
M_r = 204.26
Triclinic, $[P \overline 1]$
a = 9.8406 (4) Å
b = 10.5739 (4) Å
c = 11.9142 (5) Å
= 96.330 (2)°
= 98.486 (3)°
= 104.497 (2)°
V = 1172.99 (8) Å³
Z = 4
Mo K radiation radiation
= 0.08 mm^-1
T = 296 (2) K
0.30 × 0.18 × 0.12 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005) T_min = 0.977, T_max = 0.986
23066 measured reflections
6000 independent reflections
2803 reflections with I > 3(I)
R_int = 0.033

Refinement

R[F² > 2(F²)] = 0.053
wR(F²) = 0.157
S = 1.04
6000 reflections
290 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.28 e Å^-3
_min = -0.23 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1O4ⁱ	0.94 (4)	1.71 (4)	2.644 (4)	175 (3)
O3-H3AO2ⁱⁱ	0.93 (4)	1.71 (4)	2.631 (3)	169 (3)
C3-H3O1	0.96 (3)	2.35 (2)	2.707 (4)	101.2 (16)
C13-H13AO2	0.96	2.28	2.759 (4)	110
C16-H16O3	0.91 (3)	2.31 (2)	2.698 (4)	105.1 (18)
C26-H26AO4	0.96	2.30	2.770 (4)	110
Symmetry codes: (i) x, y, z+1; (ii) x, y, z-1.

Data collection: APEX2 (Bruker, 2007); cell refinement: APEX2; data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: JH2064 ).

Acknowledgements

The authors acknowledge the Higher Education Commission, Islamabad, Pakistan, for funding the purchase of the diffractometer and for financial support to NM for PhD studies under the Indigenous Scholarship Scheme.

References

Bruker (2005). SADABS. Bruker AXS Inc. Madison, Wisconsin, USA.
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc. Madison, Wisconsin, USA.
Burt, S. (2004). Int. J. Food Microbiol. 94, 223-253.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Hertog, M. G., Kromhout, D., Aravanis, C., Blackburn, H., Buzina, R., Fidanza, F., Giampaoli, S., Jansen, A., Menotti, A. & Nedeljkovic, S. (1995). Arch. Intern. Med. 155, 381-386.
Ma, G. & Hayes, S. E. (2004). J. Labelled Compd Radiopharm. 47, 895-901.
Muhammad, N., Zia-ur-Rehman, , Ali, S. & Meetsma, A. (2007). Acta Cryst. E63, o2174-o2175.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.

organic compounds