2-(4-Isopropyl­benzylidene)propanoic acid

Niaz Muhammad; M Nawaz Tahir; Saqib Ali; Zia-ur-Rehman; Muhammad Akram Kashmiri

doi:10.1107/S1600536808020801

. 2008 Jul 12;64(Pt 8):o1456. doi: 10.1107/S1600536808020801

2-(4-Isopropylbenzylidene)propanoic acid

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

PMCID: PMC2962086 PMID: 21203170

Abstract

The two molecules in the asymmetric unit of the title compound, C₁₃H₁₆O₂, form dimers through O—H⋯O hydrogen bonding, resulting in R ₂ ²(8) rings. Each carboxyl O atom is involved in interamolecular C—H⋯O 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 π 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,
a = 9.8406 (4) Å
b = 10.5739 (4) Å
c = 11.9142 (5) Å
α = 96.330 (2)°
β = 98.486 (3)°
γ = 104.497 (2)°
V = 1172.99 (8) Å³
Z = 4
Mo Kα radiation radiation
μ = 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 > 3σ(I)
R _int = 0.033

Refinement

R[F ² > 2σ(F ²)] = 0.053
wR(F ²) = 0.157
S = 1.04
6000 reflections
290 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.23 e Å⁻³

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 Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808020801/jh2064sup1.cif

e-64-o1456-sup1.cif^{(26.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808020801/jh2064Isup2.hkl

e-64-o1456-Isup2.hkl^{(287.8KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O4ⁱ	0.94 (4)	1.71 (4)	2.644 (4)	175 (3)
O3—H3A⋯O2ⁱⁱ	0.93 (4)	1.71 (4)	2.631 (3)	169 (3)
C3—H3⋯O1	0.96 (3)	2.35 (2)	2.707 (4)	101.2 (16)
C13—H13A⋯O2	0.96	2.28	2.759 (4)	110
C16—H16⋯O3	0.91 (3)	2.31 (2)	2.698 (4)	105.1 (18)
C26—H26A⋯O4	0.96	2.30	2.770 (4)	110

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

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.

supplementary crystallographic information

Comment

Cinnamic acids and their derivatives are widely used chemicals in a variety of fields (Ma & Hayes, 2004). They posses antibacterial, antifungal and parasite fighting abilities (Burt, 2004). A derivative of cinnamic acid is an important pharmaceutical for high blood pressure and stroke prevention and possess antitumour activity (Hertog et al., 1995).

The crystal structure of 3-(4-Bromophenyl)-2-methylacrylic acid (Muhammad et al., 2007) has been reported. The title compound (I) have a replacement of Br-atom with isopropyl at the same position. The ligand has been prepared to synthesize various organotin complexes.

The crystallographic asymmetric unit consists of two ligands. These two ligands form dimers through O—H···O hydrogen bonding with each other by completing a R₂²(8) rings (Table 1, Fig 2). Each O-atom of carboxylate ligands is involved in interamolecular H-bonds of C—H···O type forming five-membered rings. The bond distances in the benzene ring (C4—C9) have values in the range 1.372 (4)–1.390 (4) Å, whereas in (C17—C22) its range is 1.374 (4)–1.384 (4) Å. The bond angle (C11—C10—C12) of isopropyl moiety is 111.2 (3)°, whereas the same for (C24—C23—C25) is 109.8 (3)°. There exist a dissimilar dihedral angles within the two moieties. The dihedral angles of the isopropyl moieties (C10/C11/C12) and (C23/C24/C25) with their adjacent benzene rings (C4—C9) and (C17—C22) have values of 86.80 (13)° and 85.06 (13)°, respectively. The dihedral angles of the moieties (C2/C3/C13) and (C15/C16/C26) with their adjacent carboxylate moities (C1/O1/O2) and (C14/O3/O4) have values of 7.65 (51)° and 7.06 (43)°, respectively, whereas with benzene rings (C4—C9) and (C17—C22), the values of their dihedral angles is 32.18 (23)° and 34.49 (20)°, respectively. The dihedral angle between the benzene rings of two ligands is 83.34 (9)°. There does not exist any kind of π-interaction.

Experimental

Compound (I) was prepared according to the reported procedure in literature (Muhammad et al., 2007). A mixture of 4-isopropylbenzaldehyde (10 mmol, 1.51 ml), methylmalonic acid (2.36 g, 20 mmol) and piperidine (20 mmol, 1.98 ml) in pyridine (12.5 ml) solution was heated on a steam-bath for 24 h. The reaction mixture was cooled and added to a mixture of 25 ml of concentrated HCl and 50 g of ice. The precipitate formed in the acidified mixture was filtered off and washed with ice-cold water. The product was recrystallized from ethanol. The yield was 80%.