2-(2,4-Dichloro­phen­yl)acetic acid

Li, J.-S.; He, Q.-X.; Li, P.-Y.

doi:10.1107/S1600536809052453

organic compounds

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Volume 66| Part 1| January 2010| Page o110

doi:10.1107/S1600536809052453

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2-(2,4-Dichlorophenyl)acetic acid

Jiang-Sheng Li,^a ^* Qi-Xi He ^b and Peng-Yu Li ^a

^aSchool of Chemistry and Biological Engineering, Changsha University of Science & Technology, Changsha 410004, People's Republic of China, and ^bCollege of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, People's Republic of China
^*Correspondence e-mail: js_li@yahoo.com.cn

(Received 4 December 2009; accepted 6 December 2009; online 12 December 2009)

In the title compound, C₈H₆Cl₂O₂, the dihedral angle between the C—C(=O)—OH carboxyl unit and the benzene ring is 70.70 (4)°. In the crystal, molecules are linked into inversion dimers by pairs of O—H⋯O hydrogen bonds. The dimers are linked into chains extending along [001] by weak C—H⋯Cl interactions.

Related literature

For background to carboxylic acids as supramolecular synthons, see: Thalladi et al. (1996 ). For related structures, see: Hodgson & Asplund (1991 ); Li et al. (2010 ).

Experimental

Crystal data

C₈H₆Cl₂O₂
M_r = 205.03
Monoclinic, P 2₁ /n
a = 10.824 (2) Å
b = 5.6061 (11) Å
c = 13.820 (3) Å
β = 91.08 (3)°
V = 838.4 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.72 mm⁻¹
T = 113 K
0.24 × 0.20 × 0.12 mm

Data collection

Rigaku Saturn CCD diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ) T_min = 0.846, T_max = 0.918
5321 measured reflections
1484 independent reflections
1237 reflections with I > 2σ(I)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.027
wR(F²) = 0.075
S = 1.10
1484 reflections
111 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.22 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	2.6689 (16)	175
C4—H4⋯Cl1ⁱⁱ	0.93	2.86	3.731 (2)	156
Symmetry codes: (i) -x+1, -y+1, -z+2; (ii) -x+1, -y, -z+1.

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809052453/hb5271sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809052453/hb5271Isup2.hkl

checkCIF report

Comment top

Carboxylic acid is a supramolecular synthon, widely used to construct supramolecular array with one to three different dimensions via hydrogen bonds (Thalladi et al., 1996). For our continuous research, we herein report the structure of the title compound (I).

In the title molecule, (Fig 1), the O1/O2/C7/C8 carboxyl unit forms an angle of 70.70 (4) A with the benzene ring. In the crystal packing, the molecules are linked into dimers by strong O—H···O H-bonding, which extend down the c axis by the aid of weak C—H···Cl H-bonding (Table 1 & Fig 2). For related structures, see: Hodgson & Asplund (1991) and Li et al. (2010).

Related literature top

For backgroud to carboxylic acids as supramolecular synthons, see: Thalladi et al. (1996). For related structures, see: Hodgson & Asplund (1991); Li et al. (2010).

Experimental top

The title compound was available from Hunan institute of Chemical Industry, received without further purification. Colourless blocks of (I) were obtained by evaporation from its solution of ethyl acetate/petroleum ether 1/2 (v/v).

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I) showing displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. The infinite chain formed via alternative O—H···O and C—H···Cl hydrogen bonding down the c axis.

2-(2,4-Dichlorophenyl)acetic acid top

Crystal data top

C₈H₆Cl₂O₂	F(000) = 416
M_r = 205.03	D_x = 1.624 Mg m⁻³
Monoclinic, P2₁/n	Melting point = 403–405 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 10.824 (2) Å	Cell parameters from 2684 reflections
b = 5.6061 (11) Å	θ = 2.4–27.9°
c = 13.820 (3) Å	µ = 0.72 mm⁻¹
β = 91.08 (3)°	T = 113 K
V = 838.4 (3) Å³	Block, colourless
Z = 4	0.24 × 0.20 × 0.12 mm

Data collection top

Rigaku Saturn CCD diffractometer	1484 independent reflections
Radiation source: rotating anode	1237 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.037
Detector resolution: 7.31 pixels mm^-1	θ_max = 25.0°, θ_min = 2.4°
ω and ϕ scans	h = −12→12
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −6→6
T_min = 0.846, T_max = 0.918	l = −10→16
5321 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.027	H-atom parameters constrained
wR(F²) = 0.075	w = 1/[σ²(F_o²) + (0.0435P)²] where P = (F_o² + 2F_c²)/3
S = 1.10	(Δ/σ)_max = 0.001
1484 reflections	Δρ_max = 0.23 e Å⁻³
111 parameters	Δρ_min = −0.22 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.073 (5)

Crystal data top

C₈H₆Cl₂O₂	V = 838.4 (3) Å³
M_r = 205.03	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.824 (2) Å	µ = 0.72 mm⁻¹
b = 5.6061 (11) Å	T = 113 K
c = 13.820 (3) Å	0.24 × 0.20 × 0.12 mm
β = 91.08 (3)°

Data collection top

Rigaku Saturn CCD diffractometer	1484 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	1237 reflections with I > 2σ(I)
T_min = 0.846, T_max = 0.918	R_int = 0.037
5321 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.027	0 restraints
wR(F²) = 0.075	H-atom parameters constrained
S = 1.10	Δρ_max = 0.23 e Å⁻³
1484 reflections	Δρ_min = −0.22 e Å⁻³
111 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
Cl1	0.71462 (4)	0.15511 (7)	0.45827 (3)	0.02309 (18)
Cl2	0.35390 (4)	0.34376 (7)	0.70900 (3)	0.02349 (18)
O1	0.55180 (10)	0.4443 (2)	0.88848 (8)	0.0230 (3)
O2	0.46215 (12)	0.7778 (2)	0.94126 (8)	0.0266 (3)
H2	0.4593	0.7022	0.9920	0.040*
C1	0.67428 (16)	0.6663 (3)	0.65565 (12)	0.0196 (4)
H1	0.7191	0.7977	0.6777	0.024*
C2	0.72229 (14)	0.5277 (3)	0.58229 (11)	0.0203 (4)
H2A	0.7977	0.5660	0.5551	0.024*
C3	0.65595 (15)	0.3314 (3)	0.55033 (11)	0.0166 (4)
C4	0.54302 (14)	0.2735 (3)	0.58966 (11)	0.0176 (4)
H4	0.4990	0.1408	0.5680	0.021*
C5	0.49744 (14)	0.4168 (3)	0.66162 (11)	0.0165 (4)
C6	0.56134 (14)	0.6155 (3)	0.69727 (11)	0.0155 (4)
C7	0.51115 (15)	0.7662 (3)	0.77720 (11)	0.0188 (4)
H7A	0.5601	0.9107	0.7826	0.023*
H7B	0.4272	0.8125	0.7601	0.023*
C8	0.51103 (15)	0.6439 (3)	0.87375 (12)	0.0173 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0220 (3)	0.0288 (3)	0.0187 (3)	0.00182 (16)	0.00584 (19)	−0.00592 (16)
Cl2	0.0160 (2)	0.0273 (3)	0.0274 (3)	−0.00391 (15)	0.00862 (19)	−0.00387 (17)
O1	0.0288 (6)	0.0256 (7)	0.0146 (6)	0.0115 (5)	0.0033 (5)	−0.0024 (5)
O2	0.0387 (8)	0.0245 (7)	0.0168 (6)	0.0114 (6)	0.0075 (6)	−0.0012 (5)
C1	0.0210 (9)	0.0183 (9)	0.0195 (9)	−0.0041 (6)	0.0008 (8)	0.0001 (7)
C2	0.0158 (8)	0.0250 (9)	0.0203 (9)	−0.0023 (7)	0.0046 (7)	0.0027 (7)
C3	0.0194 (8)	0.0192 (9)	0.0114 (8)	0.0035 (7)	0.0018 (7)	0.0015 (6)
C4	0.0179 (8)	0.0182 (8)	0.0168 (8)	−0.0013 (7)	−0.0004 (7)	−0.0024 (7)
C5	0.0130 (8)	0.0213 (8)	0.0153 (8)	−0.0004 (6)	0.0017 (6)	0.0047 (7)
C6	0.0193 (8)	0.0161 (8)	0.0111 (8)	0.0013 (6)	−0.0003 (7)	0.0028 (6)
C7	0.0210 (8)	0.0163 (8)	0.0191 (9)	0.0007 (7)	0.0004 (7)	−0.0005 (7)
C8	0.0135 (8)	0.0232 (10)	0.0151 (8)	0.0003 (6)	0.0017 (7)	−0.0044 (6)

Geometric parameters (Å, º) top

Cl1—C3	1.7405 (16)	C2—H2A	0.9300
Cl2—C5	1.7460 (16)	C3—C4	1.386 (2)
O1—C8	1.2185 (19)	C4—C5	1.377 (2)
O2—C8	1.316 (2)	C4—H4	0.9300
O2—H2	0.8200	C5—C6	1.396 (2)
C1—C2	1.386 (2)	C6—C7	1.501 (2)
C1—C6	1.390 (2)	C7—C8	1.500 (2)
C1—H1	0.9300	C7—H7A	0.9700
C2—C3	1.382 (2)	C7—H7B	0.9700

C8—O2—H2	109.5	C4—C5—Cl2	117.86 (12)
C2—C1—C6	122.16 (15)	C6—C5—Cl2	119.55 (13)
C2—C1—H1	118.9	C1—C6—C5	116.81 (15)
C6—C1—H1	118.9	C1—C6—C7	121.50 (14)
C3—C2—C1	118.72 (15)	C5—C6—C7	121.68 (15)
C3—C2—H2A	120.6	C8—C7—C6	113.81 (13)
C1—C2—H2A	120.6	C8—C7—H7A	108.8
C2—C3—C4	121.21 (15)	C6—C7—H7A	108.8
C2—C3—Cl1	119.43 (13)	C8—C7—H7B	108.8
C4—C3—Cl1	119.36 (12)	C6—C7—H7B	108.8
C5—C4—C3	118.50 (15)	H7A—C7—H7B	107.7
C5—C4—H4	120.7	O1—C8—O2	123.67 (16)
C3—C4—H4	120.7	O1—C8—C7	124.19 (15)
C4—C5—C6	122.59 (15)	O2—C8—C7	112.14 (13)

C6—C1—C2—C3	−0.6 (2)	C4—C5—C6—C1	0.9 (2)
C1—C2—C3—C4	0.5 (2)	Cl2—C5—C6—C1	−179.10 (11)
C1—C2—C3—Cl1	179.98 (12)	C4—C5—C6—C7	−178.68 (14)
C2—C3—C4—C5	0.2 (2)	Cl2—C5—C6—C7	1.3 (2)
Cl1—C3—C4—C5	−179.22 (11)	C1—C6—C7—C8	−109.95 (17)
C3—C4—C5—C6	−1.0 (2)	C5—C6—C7—C8	69.59 (19)
C3—C4—C5—Cl2	179.02 (11)	C6—C7—C8—O1	2.7 (2)
C2—C1—C6—C5	−0.1 (2)	C6—C7—C8—O2	−177.59 (13)
C2—C1—C6—C7	179.49 (14)

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	2.6689 (16)	175
C4—H4···Cl1ⁱⁱ	0.93	2.86	3.731 (2)	156

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

Experimental details

Crystal data
Chemical formula	C₈H₆Cl₂O₂
M_r	205.03
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	113
a, b, c (Å)	10.824 (2), 5.6061 (11), 13.820 (3)
β (°)	91.08 (3)
V (Å³)	838.4 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.72
Crystal size (mm)	0.24 × 0.20 × 0.12

Data collection
Diffractometer	Rigaku Saturn CCD diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2005)
T_min, T_max	0.846, 0.918
No. of measured, independent and observed [I > 2σ(I)] reflections	5321, 1484, 1237
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.027, 0.075, 1.10
No. of reflections	1484
No. of parameters	111
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.22

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

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	2.6689 (16)	175
C4—H4···Cl1ⁱⁱ	0.93	2.86	3.731 (2)	156

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

References

Hodgson, D. J. & Asplund, R. O. (1991). Acta Cryst. C47, 1986–1987. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Li, J.-S., He, Q.-X. & Li, P.-Y. (2010). Acta Cryst. E66, o39. Web of Science CSD CrossRef IUCr Journals Google Scholar
Rigaku/MSC (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Thalladi, V. R., goud, B. S., Hoy, V. J., Allen, F. H., Howard, J. A. K. & Desiraju, G. R. (1996). Chem. Commun. pp. 401–402. CSD CrossRef Web of Science Google Scholar

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CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 1| January 2010| Page o110

doi:10.1107/S1600536809052453

Open

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