2-(2-Chloro­phen­yl)acetic acid

Kant, R.; Gupta, V.K.; Kapoor, K.; Narayana, B.

doi:10.1107/S1600536812023938

organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1940

doi:10.1107/S1600536812023938

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2-(2-Chlorophenyl)acetic acid

Rajni Kant,^a ^* Vivek K. Gupta,^a Kamini Kapoor ^a and B. Narayana ^b

^aX-ray Crystallography Laboratory, Post-Graduate Department of Physics & Electronics, University of Jammu, Jammu Tawi 180 006, India, and ^bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India
^*Correspondence e-mail: rkvk.paper11@gmail.com

(Received 24 May 2012; accepted 25 May 2012; online 31 May 2012)

In the title compound, C₈H₇ClO₂, the carboxyl group forms a dihedral angle of 74.83 (9)° with the benzene ring plane. In the crystal, molecules are linked into inversion dimers by pairs of O—H⋯O hydrogen bonds. The dimers are linked into layers parallel to the bc plane by weak C—H⋯O interactions.

Related literature

For applications of phenylacetic acids, see: Castellari & Ottani (1995 ); Deshpande et al. (2008 ); Hata et al. (1986 ). For the crystal structure of isostructural 2-(2-bromophenyl)acetic acid, see: Kant et al. (2012 ).

Experimental

Crystal data

C₈H₇ClO₂
M_r = 170.59
Monoclinic, P 2₁ /c
a = 9.1473 (7) Å
b = 5.8265 (3) Å
c = 15.4299 (7) Å
β = 101.155 (5)°
V = 806.83 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.42 mm⁻¹
T = 293 K
0.3 × 0.2 × 0.2 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.748, T_max = 1.000
9367 measured reflections
1583 independent reflections
1173 reflections with I > 2σ(I)
R_int = 0.045

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.145
S = 1.06
1583 reflections
100 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O10—H10⋯O9ⁱ	0.82	1.82	2.639 (4)	173
C6—H6⋯O9ⁱⁱ	0.93	2.57	3.469 (4)	163
Symmetry codes: (i) -x+2, -y, -z+1; (ii) $[-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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 ); software used to prepare material for publication: PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536812023938/gk2495sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812023938/gk2495Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812023938/gk2495Isup3.cml

checkCIF report

Comment top

Derivatives of phenyl acetic acids are used as ingredients in perfume to provide honey like odour, for the preparation of a nonsteroidal anti-inflammatory drug like diclofenac (Hata et al., 1986; Castellari & Ottani, 1995), and as intermediate compounds for the synthesis of heterocyclic compounds (Deshpande et al., 2008). In continuation of our work on substituted phenylacetic acid (Kant et al., 2012), we report the crystal structure of a new derivative, 2-(2-chlorophenyl)acetic acid (I). The title compound is closely isostructural with its bromo analogue (Kant et al., 2012).

Related literature top

For applications of phenylacetic acids , see: Castellari & Ottani (1995); Deshpande et al. (2008); Hata et al. (1986). For the crystal structure of isostructural 2-(2-bromophenyl)acetic acid, see: Kant et al. (2012).

Experimental top

The title compound was purchased from the Spectrochem Ltd. and single crystal was grown from ethyl acetate and toluene (1:1) mixture by slow evaporation method (m.p. 366–369 K).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); 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); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. ORTEP view of the molecule with displacement ellipsoids are drawn at the 40% probability level. H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. Projection of the crystal packing along the b axis. Hydrogen atoms are omitted for clarity and hydrogen bonds are shown with dashed lines.

2-(2-Chlorophenyl)acetic acid top

Crystal data top

C₈H₇ClO₂	F(000) = 352
M_r = 170.59	D_x = 1.404 Mg m⁻³
Monoclinic, P2₁/c	Melting point = 369–366 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 9.1473 (7) Å	Cell parameters from 3981 reflections
b = 5.8265 (3) Å	θ = 3.5–29.1°
c = 15.4299 (7) Å	µ = 0.42 mm⁻¹
β = 101.155 (5)°	T = 293 K
V = 806.83 (8) Å³	Block, colourless
Z = 4	0.3 × 0.2 × 0.2 mm

Data collection top

Oxford Diffraction Xcalibur Sapphire3 diffractometer	1583 independent reflections
Radiation source: fine-focus sealed tube	1173 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.045
Detector resolution: 16.1049 pixels mm^-1	θ_max = 26.0°, θ_min = 3.8°
ω scans	h = −11→11
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −7→7
T_min = 0.748, T_max = 1.000	l = −19→19
9367 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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.145	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0608P)² + 0.4607P] where P = (F_o² + 2F_c²)/3
1583 reflections	(Δ/σ)_max = 0.001
100 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

C₈H₇ClO₂	V = 806.83 (8) Å³
M_r = 170.59	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.1473 (7) Å	µ = 0.42 mm⁻¹
b = 5.8265 (3) Å	T = 293 K
c = 15.4299 (7) Å	0.3 × 0.2 × 0.2 mm
β = 101.155 (5)°

Data collection top

Oxford Diffraction Xcalibur Sapphire3 diffractometer	1583 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	1173 reflections with I > 2σ(I)
T_min = 0.748, T_max = 1.000	R_int = 0.045
9367 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.145	H-atom parameters constrained
S = 1.06	Δρ_max = 0.30 e Å⁻³
1583 reflections	Δρ_min = −0.33 e Å⁻³
100 parameters

Special details top

Experimental. CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27–08-2010 CrysAlis171. NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
Cl1	0.58539 (10)	0.25918 (15)	0.57120 (5)	0.0721 (3)
C1	0.7450 (3)	0.0180 (4)	0.70745 (16)	0.0451 (6)
C2	0.6591 (3)	0.2111 (4)	0.68252 (16)	0.0447 (6)
C3	0.6269 (3)	0.3678 (5)	0.74270 (18)	0.0516 (7)
H3	0.5691	0.4962	0.7238	0.062*
C4	0.6811 (4)	0.3324 (5)	0.8313 (2)	0.0599 (8)
H4	0.6599	0.4369	0.8727	0.072*
C5	0.7665 (4)	0.1427 (6)	0.85832 (19)	0.0657 (9)
H5	0.8028	0.1180	0.9182	0.079*
C6	0.7986 (4)	−0.0111 (5)	0.79697 (19)	0.0602 (8)
H6	0.8577	−0.1380	0.8162	0.072*
C7	0.7754 (4)	−0.1586 (5)	0.6417 (2)	0.0604 (8)
H7A	0.8219	−0.2908	0.6740	0.073*
H7B	0.6808	−0.2086	0.6070	0.073*
C8	0.8723 (3)	−0.0803 (5)	0.57996 (18)	0.0527 (7)
O9	0.9496 (2)	0.0930 (4)	0.59199 (13)	0.0672 (6)
O10	0.8700 (3)	−0.2177 (4)	0.51387 (14)	0.0729 (7)
H10	0.9245	−0.1674	0.4820	0.109*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0835 (7)	0.0807 (6)	0.0476 (4)	−0.0019 (4)	0.0015 (4)	0.0124 (4)
C1	0.0496 (16)	0.0395 (13)	0.0501 (14)	−0.0030 (11)	0.0193 (12)	0.0039 (11)
C2	0.0466 (15)	0.0484 (15)	0.0403 (12)	−0.0089 (12)	0.0117 (11)	0.0049 (11)
C3	0.0537 (17)	0.0421 (14)	0.0629 (16)	0.0005 (12)	0.0206 (13)	0.0032 (13)
C4	0.070 (2)	0.0558 (17)	0.0571 (17)	−0.0072 (15)	0.0218 (15)	−0.0096 (14)
C5	0.076 (2)	0.077 (2)	0.0423 (14)	−0.0015 (18)	0.0081 (14)	0.0044 (15)
C6	0.065 (2)	0.0565 (17)	0.0597 (17)	0.0089 (15)	0.0142 (14)	0.0149 (14)
C7	0.076 (2)	0.0430 (15)	0.0692 (18)	−0.0054 (15)	0.0318 (16)	−0.0039 (14)
C8	0.0549 (17)	0.0486 (15)	0.0576 (16)	−0.0054 (14)	0.0184 (13)	−0.0096 (13)
O9	0.0748 (15)	0.0647 (13)	0.0710 (13)	−0.0229 (12)	0.0362 (11)	−0.0244 (11)
O10	0.0876 (17)	0.0699 (14)	0.0708 (14)	−0.0292 (12)	0.0393 (12)	−0.0291 (11)

Geometric parameters (Å, º) top

Cl1—C2	1.742 (3)	C5—C6	1.376 (4)
C1—C2	1.384 (4)	C5—H5	0.9300
C1—C6	1.384 (4)	C6—H6	0.9300
C1—C7	1.508 (4)	C7—C8	1.492 (4)
C2—C3	1.374 (4)	C7—H7A	0.9700
C3—C4	1.377 (4)	C7—H7B	0.9700
C3—H3	0.9300	C8—O9	1.227 (3)
C4—C5	1.370 (5)	C8—O10	1.293 (3)
C4—H4	0.9300	O10—H10	0.8200

C2—C1—C6	116.7 (2)	C6—C5—H5	120.0
C2—C1—C7	122.4 (2)	C5—C6—C1	121.7 (3)
C6—C1—C7	120.8 (3)	C5—C6—H6	119.1
C3—C2—C1	122.5 (2)	C1—C6—H6	119.1
C3—C2—Cl1	117.8 (2)	C8—C7—C1	115.5 (2)
C1—C2—Cl1	119.7 (2)	C8—C7—H7A	108.4
C2—C3—C4	119.2 (3)	C1—C7—H7A	108.4
C2—C3—H3	120.4	C8—C7—H7B	108.4
C4—C3—H3	120.4	C1—C7—H7B	108.4
C5—C4—C3	119.8 (3)	H7A—C7—H7B	107.5
C5—C4—H4	120.1	O9—C8—O10	123.3 (3)
C3—C4—H4	120.1	O9—C8—C7	123.5 (2)
C4—C5—C6	120.1 (3)	O10—C8—C7	113.2 (2)
C4—C5—H5	120.0	C8—O10—H10	109.5

C6—C1—C2—C3	−0.2 (4)	C4—C5—C6—C1	−0.9 (5)
C7—C1—C2—C3	177.6 (3)	C2—C1—C6—C5	0.8 (4)
C6—C1—C2—Cl1	−179.2 (2)	C7—C1—C6—C5	−177.0 (3)
C7—C1—C2—Cl1	−1.4 (4)	C2—C1—C7—C8	68.3 (4)
C1—C2—C3—C4	−0.3 (4)	C6—C1—C7—C8	−114.0 (3)
Cl1—C2—C3—C4	178.8 (2)	C1—C7—C8—O9	15.7 (5)
C2—C3—C4—C5	0.2 (4)	C1—C7—C8—O10	−166.3 (3)
C3—C4—C5—C6	0.4 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O10—H10···O9ⁱ	0.82	1.82	2.639 (4)	173
C6—H6···O9ⁱⁱ	0.93	2.57	3.469 (4)	163

Symmetry codes: (i) −x+2, −y, −z+1; (ii) −x+2, y−1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₈H₇ClO₂
M_r	170.59
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	9.1473 (7), 5.8265 (3), 15.4299 (7)
β (°)	101.155 (5)
V (Å³)	806.83 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.42
Crystal size (mm)	0.3 × 0.2 × 0.2

Data collection
Diffractometer	Oxford Diffraction Xcalibur Sapphire3 diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)
T_min, T_max	0.748, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	9367, 1583, 1173
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.145, 1.06
No. of reflections	1583
No. of parameters	100
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.33

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O10—H10···O9ⁱ	0.82	1.82	2.639 (4)	173
C6—H6···O9ⁱⁱ	0.93	2.57	3.469 (4)	163

Symmetry codes: (i) −x+2, −y, −z+1; (ii) −x+2, y−1/2, −z+3/2.

Acknowledgements

RK acknowledges the Department of Science & Technology for access to the single-crystal X-ray diffractometer sanctioned as a National Facility under project No. SR/S2/CMP-47/2003 and the University of Jammu, Jammu, India, for financial support. BN thanks the UGC for financial assistance through the BSR one-time grant for the purchase of chemicals.

References

Castellari, C. & Ottani, S. (1995). Acta Cryst. C51, 2612–2615. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Deshpande, P. P., Nanduri, V. B., Pullockaran, A., Christie, H., Mueller, R. H. & Patel, R. N. (2008). J. Ind. Microbiol. Biotechnol. 35, 901–906. Web of Science CrossRef PubMed CAS Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Hata, T., Sato, S. & Tamura, C. (1986). Acta Cryst. C42, 452–454. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Kant, R., Kapoor, K. & Narayana, B. (2012). Acta Cryst. E68, o1704. CSD CrossRef IUCr Journals Google Scholar
Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar