3-(4-Ethoxy­benzo­yl)propionic acid

Ali, S.; Hasan, A.; Rama, N.H.; Badshah, A.; Ruzicka, A.

doi:10.1107/S1600536808034429

organic compounds

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ISSN: 2056-9890

Volume 64| Part 11| November 2008| Page o2206

doi:10.1107/S1600536808034429

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3-(4-Ethoxybenzoyl)propionic acid

Sajid Ali,^a Aurangzeb Hasan,^a ^* Nasim Hasan Rama,^a Amir Badshah ^a and Ales Ruczika ^b

^aDepartment of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan, and ^bDepartment of General and Inorganic Chemistry, Faculty of Chemical Technology, University of Pardubice, Nam. Cs. Legii' 565, 53210 Pardubice, Czech Republic
^*Correspondence e-mail: nasimhrama@yahoo.com

(Received 18 October 2008; accepted 21 October 2008; online 25 October 2008)

The title compound, C₁₂H₁₄O₄, is an important intermediate in the synthesis of biologically active heterocyclic compounds. In the crystal structure, intermolecular O—H⋯O and C—H⋯O hydrogen bonds link the molecules. There are also C—H⋯π contacts between the benzene ring and the methylene groups.

Related literature

For general background, see: Hashem et al. (2007 ); Husain et al. (2005 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₂H₁₄O₄
M_r = 222.23
Triclinic, $[P \overline 1]$
a = 7.8371 (3) Å
b = 8.7399 (5) Å
c = 9.8140 (5) Å
α = 106.993 (4)°
β = 107.541 (4)°
γ = 107.142 (4)°
V = 556.34 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 150 (1) K
0.34 × 0.32 × 0.31 mm

Data collection

Bruker–Nonius KappaCCD area-detector diffractometer
Absorption correction: Gaussian (Coppens, 1970 ) T_min = 0.964, T_max = 0.987
8993 measured reflections
2508 independent reflections
2089 reflections with I > 2σ(I)
R_int = 0.059

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.123
S = 1.11
2508 reflections
145 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1ⁱ	0.82	1.85	2.664 (3)	172
C2—H2B⋯O3ⁱⁱ	0.97	2.44	3.386 (3)	165
C11—H11B⋯O3ⁱⁱⁱ	0.97	2.50	3.445 (3)	166
C3—H3B⋯Cg1^iv	0.97	2.66	3.528 (3)	150
C11—H11A⋯Cg1^v	0.97	2.84	3.679 (3)	145
Symmetry codes: (i) -x, -y+1, -z; (ii) -x, -y, -z; (iii) x+1, y, z; (iv) -x+1, -y, -z; (v) -x+2, -y+1, -z+1. Cg1 is the centroid of the phenyl ring.

Data collection: COLLECT (Hooft, 1998 ); cell refinement: COLLECT and DENZO (Otwinowski & Minor, 1997 ); data reduction: COLLECT and DENZO; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808034429/hk2555sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808034429/hk2555Isup2.hkl

checkCIF report

Comment top

Benzoyl propionic acids are important intermediates in heterocyclic chemistry and have been used for the synthesis of various biologically active five -membered heterocyles such as butenolides, pyrrolones (Husain et al., 2005), oxadiazoles and triazoles (Hashem et al., 2007). In view of the versatility of these compounds, we synthesized the title compound and reported herein its crystal structure.

In the title compound (Fig. 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges . O4, C2, C3, C4, C11 and C12 atoms are -0.011 (3), 0.162 (4), 0.189 (4), -0.09 (3), -0.143 (3) and -0.151 (3) Å away from the phenyl plane, respectively.

In the crystal structure, intermolecular O-H···O and C-H···O hydrogen bonds (Table 1) link the molecules (Fig. 2), in which they may be effective in the stabilization of the structure. There also exist C—H···π contacts (Table 1) between the phenyl ring and the methylene groups.

Related literature top

For general background, see: Hashem et al. (2007); Husain et al. (2005). For bond-length data, see: Allen et al. (1987). Cg1 is the centroid of the phenyl ring.

Experimental top

The title compound was synthesized by the condensation of succinic anhydride (2 g, 20 mmol) with 1-ethoxybenzene (10 ml) in the presence of alumium chloride (6 g, 42 mmol). The reaction mixture was refluxed for 4 h. After completion of the reaction, excess solvent (Anisol) was removed by steam distillation. The resultant solid product was purified by dissolving it in sodium hydroxide solution (5%, w/v), filtering followed by addition of hydrochloric acid. The obtained solid mass was filtered, washed with cold water, dried and crystallized from methanol (yield; 67%, m.p. 404-405 K).

Computing details top

Data collection: COLLECT (Hooft, 1998); cell refinement: COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997); data reduction: COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme.
	Fig. 2. A partial packing diagram. Hydrogen bonds are shown as dashed lines.
	Fig. 3. The formation of the title compound.

3-(4-Ethoxybenzoyl)propionic acid top

Crystal data top

C₁₂H₁₄O₄	Z = 2
M_r = 222.23	F(000) = 236
Triclinic, P1	D_x = 1.327 Mg m⁻³
Hall symbol: -P 1	Melting point: 404(1) K
a = 7.8371 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.7399 (5) Å	Cell parameters from 9044 reflections
c = 9.8140 (5) Å	θ = 1–27.5°
α = 106.993 (4)°	µ = 0.10 mm⁻¹
β = 107.541 (4)°	T = 150 K
γ = 107.142 (4)°	Block, colorless
V = 556.34 (6) Å³	0.34 × 0.32 × 0.31 mm

Data collection top

Bruker–Nonius KappaCCD area-detector diffractometer	2508 independent reflections
Radiation source: fine-focus sealed tube	2089 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.059
Detector resolution: 9.091 pixels mm^-1	θ_max = 27.5°, θ_min = 2.4°
ϕ and ω scans	h = −10→10
Absorption correction: gaussian (Coppens, 1970)	k = −11→11
T_min = 0.964, T_max = 0.987	l = −12→12
8993 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.123	H-atom parameters constrained
S = 1.11	w = 1/[σ²(F_o²) + (0.0401P)² + 0.2871P] where P = (F_o² + 2F_c²)/3
2508 reflections	(Δ/σ)_max < 0.001
145 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₂H₁₄O₄	γ = 107.142 (4)°
M_r = 222.23	V = 556.34 (6) Å³
Triclinic, P1	Z = 2
a = 7.8371 (3) Å	Mo Kα radiation
b = 8.7399 (5) Å	µ = 0.10 mm⁻¹
c = 9.8140 (5) Å	T = 150 K
α = 106.993 (4)°	0.34 × 0.32 × 0.31 mm
β = 107.541 (4)°

Data collection top

Bruker–Nonius KappaCCD area-detector diffractometer	2508 independent reflections
Absorption correction: gaussian (Coppens, 1970)	2089 reflections with I > 2σ(I)
T_min = 0.964, T_max = 0.987	R_int = 0.059
8993 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.123	H-atom parameters constrained
S = 1.11	Δρ_max = 0.22 e Å⁻³
2508 reflections	Δρ_min = −0.24 e Å⁻³
145 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.19232 (17)	0.45879 (16)	0.01166 (16)	0.0387 (3)
O2	−0.11942 (17)	0.27131 (16)	−0.14840 (16)	0.0419 (3)
H2	−0.1388	0.3584	−0.1118	0.050*
O3	0.21830 (18)	0.16047 (18)	0.13387 (15)	0.0373 (3)
O4	1.07552 (17)	0.25792 (17)	0.51668 (14)	0.0352 (3)
C1	0.0717 (2)	0.3129 (2)	−0.08709 (19)	0.0287 (3)
C2	0.1221 (2)	0.1655 (2)	−0.15467 (19)	0.0295 (3)
H2A	0.1061	0.1493	−0.2606	0.035*
H2B	0.0308	0.0577	−0.1615	0.035*
C3	0.3310 (2)	0.1968 (2)	−0.05809 (19)	0.0279 (3)
H3A	0.4210	0.3134	−0.0364	0.033*
H3B	0.3658	0.1115	−0.1184	0.033*
C4	0.3542 (2)	0.1827 (2)	0.09544 (18)	0.0261 (3)
C5	0.5470 (2)	0.1981 (2)	0.19915 (18)	0.0258 (3)
C6	0.5593 (2)	0.1507 (2)	0.32477 (19)	0.0302 (4)
H6	0.4458	0.1043	0.3385	0.036*
C7	0.7366 (3)	0.1717 (2)	0.4281 (2)	0.0322 (4)
H7	0.7427	0.1394	0.5111	0.039*
C8	0.9075 (2)	0.2414 (2)	0.40859 (19)	0.0293 (3)
C9	0.8975 (2)	0.2867 (2)	0.2828 (2)	0.0326 (4)
H9	1.0105	0.3314	0.2679	0.039*
C10	0.7176 (2)	0.2637 (2)	0.1798 (2)	0.0306 (4)
H10	0.7107	0.2933	0.0952	0.037*
C11	1.2575 (2)	0.3431 (2)	0.5103 (2)	0.0338 (4)
H11A	1.2781	0.4618	0.5209	0.041*
H11B	1.2554	0.2783	0.4105	0.041*
C12	1.4192 (3)	0.3482 (3)	0.6432 (2)	0.0424 (4)
H12A	1.4192	0.4118	0.7412	0.051*
H12B	1.5439	0.4059	0.6429	0.051*
H12C	1.3981	0.2300	0.6308	0.051*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0274 (6)	0.0308 (6)	0.0479 (8)	0.0141 (5)	0.0076 (5)	0.0101 (6)
O2	0.0270 (6)	0.0365 (7)	0.0490 (8)	0.0156 (5)	0.0077 (6)	0.0076 (6)
O3	0.0318 (6)	0.0519 (8)	0.0351 (7)	0.0193 (6)	0.0182 (5)	0.0212 (6)
O4	0.0299 (6)	0.0454 (7)	0.0319 (6)	0.0157 (5)	0.0100 (5)	0.0213 (6)
C1	0.0257 (8)	0.0316 (8)	0.0305 (8)	0.0125 (7)	0.0099 (7)	0.0170 (7)
C2	0.0294 (8)	0.0327 (8)	0.0249 (8)	0.0138 (7)	0.0094 (6)	0.0116 (6)
C3	0.0294 (8)	0.0308 (8)	0.0278 (8)	0.0166 (7)	0.0129 (7)	0.0130 (7)
C4	0.0292 (8)	0.0233 (7)	0.0267 (8)	0.0121 (6)	0.0132 (6)	0.0091 (6)
C5	0.0297 (8)	0.0256 (7)	0.0248 (8)	0.0144 (6)	0.0118 (6)	0.0110 (6)
C6	0.0321 (8)	0.0338 (8)	0.0308 (8)	0.0157 (7)	0.0172 (7)	0.0155 (7)
C7	0.0369 (9)	0.0364 (9)	0.0290 (8)	0.0169 (7)	0.0154 (7)	0.0178 (7)
C8	0.0311 (8)	0.0295 (8)	0.0272 (8)	0.0151 (7)	0.0095 (7)	0.0122 (7)
C9	0.0293 (8)	0.0389 (9)	0.0347 (9)	0.0145 (7)	0.0156 (7)	0.0197 (8)
C10	0.0322 (8)	0.0382 (9)	0.0286 (8)	0.0170 (7)	0.0146 (7)	0.0192 (7)
C11	0.0305 (8)	0.0383 (9)	0.0297 (9)	0.0135 (7)	0.0103 (7)	0.0141 (7)
C12	0.0325 (9)	0.0505 (11)	0.0374 (10)	0.0138 (8)	0.0088 (8)	0.0196 (9)

Geometric parameters (Å, º) top

O2—H2	0.8200	C5—C10	1.384 (2)
O3—C4	1.2156 (19)	C6—C7	1.373 (2)
O4—C8	1.3552 (19)	C6—H6	0.9300
O4—C11	1.431 (2)	C7—H7	0.9300
C1—O1	1.214 (2)	C8—C7	1.394 (2)
C1—O2	1.3210 (19)	C8—C9	1.390 (2)
C1—C2	1.488 (2)	C9—H9	0.9300
C2—H2A	0.9700	C10—C9	1.381 (2)
C2—H2B	0.9701	C10—H10	0.9300
C3—C2	1.517 (2)	C11—C12	1.500 (2)
C3—C4	1.508 (2)	C11—H11A	0.9700
C3—H3A	0.9700	C11—H11B	0.9700
C3—H3B	0.9700	C12—H12A	0.9599
C5—C4	1.487 (2)	C12—H12B	0.9600
C5—C6	1.397 (2)	C12—H12C	0.9600

C1—O2—H2	109.5	C5—C6—H6	119.6
C8—O4—C11	117.96 (13)	C6—C7—C8	120.05 (15)
O1—C1—O2	122.54 (15)	C6—C7—H7	120.0
O1—C1—C2	124.21 (14)	C8—C7—H7	120.0
O2—C1—C2	113.22 (14)	O4—C8—C9	124.30 (15)
C1—C2—C3	112.93 (14)	O4—C8—C7	115.80 (14)
C1—C2—H2A	109.0	C9—C8—C7	119.89 (15)
C3—C2—H2A	109.0	C10—C9—C8	119.16 (15)
C1—C2—H2B	109.0	C10—C9—H9	120.4
C3—C2—H2B	108.9	C8—C9—H9	120.4
H2A—C2—H2B	107.8	C9—C10—C5	121.76 (15)
C4—C3—C2	111.95 (13)	C9—C10—H10	119.2
C4—C3—H3A	109.1	C5—C10—H10	119.1
C2—C3—H3A	109.1	O4—C11—C12	107.39 (14)
C4—C3—H3B	109.4	O4—C11—H11A	110.2
C2—C3—H3B	109.4	C12—C11—H11A	110.3
H3A—C3—H3B	107.9	O4—C11—H11B	110.3
O3—C4—C5	120.78 (14)	C12—C11—H11B	110.2
O3—C4—C3	120.57 (14)	H11A—C11—H11B	108.5
C5—C4—C3	118.65 (13)	C11—C12—H12A	109.4
C10—C5—C6	118.30 (15)	C11—C12—H12B	109.5
C10—C5—C4	122.60 (14)	H12A—C12—H12B	109.5
C6—C5—C4	119.06 (14)	C11—C12—H12C	109.5
C7—C6—C5	120.82 (15)	H12A—C12—H12C	109.5
C7—C6—H6	119.6	H12B—C12—H12C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1ⁱ	0.82	1.85	2.664 (3)	172
C2—H2B···O3ⁱⁱ	0.97	2.44	3.386 (3)	165
C11—H11B···O3ⁱⁱⁱ	0.97	2.50	3.445 (3)	166
C3—H3B···Cg1^iv	0.97	2.66	3.528 (3)	150
C11—H11A···Cg1^v	0.97	2.84	3.679 (3)	145

Symmetry codes: (i) −x, −y+1, −z; (ii) −x, −y, −z; (iii) x+1, y, z; (iv) −x+1, −y, −z; (v) −x+2, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₂H₁₄O₄
M_r	222.23
Crystal system, space group	Triclinic, P1
Temperature (K)	150
a, b, c (Å)	7.8371 (3), 8.7399 (5), 9.8140 (5)
α, β, γ (°)	106.993 (4), 107.541 (4), 107.142 (4)
V (Å³)	556.34 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.34 × 0.32 × 0.31

Data collection
Diffractometer	Bruker–Nonius KappaCCD area-detector diffractometer
Absorption correction	Gaussian (Coppens, 1970)
T_min, T_max	0.964, 0.987
No. of measured, independent and observed [I > 2σ(I)] reflections	8993, 2508, 2089
R_int	0.059
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.123, 1.11
No. of reflections	2508
No. of parameters	145
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.24

Computer programs: , COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1ⁱ	0.82	1.85	2.664 (3)	172
C2—H2B···O3ⁱⁱ	0.97	2.44	3.386 (3)	165
C11—H11B···O3ⁱⁱⁱ	0.97	2.50	3.445 (3)	166
C3—H3B···Cg1^iv	0.97	2.66	3.528 (3)	150
C11—H11A···Cg1^v	0.97	2.84	3.679 (3)	145

Symmetry codes: (i) −x, −y+1, −z; (ii) −x, −y, −z; (iii) x+1, y, z; (iv) −x+1, −y, −z; (v) −x+2, −y+1, −z+1.

Acknowledgements

The authors gratefully acknowledge funds from the Higher Education Commission, Islamabad, Pakistan.

References

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