Methyl 2,5-dichloro-benzoate.

In the mol-ecule of the title compound, C(8)H(6)Cl(2)O(2), the benzene ring is oriented with respect to the planar ester group at a dihedral angle of 39.22 (3)°.

Related literature

For general background, see: Zheng et al. (2003 ▶); Al-Talib et al. (1990 ▶); Yousif et al. (1986 ▶); Ahmad et al. (2001 ▶); Al-Soud et al. (2004 ▶); El-Emam et al. (2004 ▶); Weinstock et al. (1991 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶); and of MOGUL, see: Bruno et al. (2004 ▶).

Experimental

Crystal data

C8H6Cl2O2

M = 205.03

Triclinic,

a = 3.8452 (3) Å

b = 7.0158 (4) Å

c = 15.8510 (10) Å

α = 77.189 (6)°

β = 89.130 (7)°

γ = 83.741 (5)°

V = 414.46 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.73 mm−1

T = 150 (1) K

0.68 × 0.11 × 0.06 mm

Data collection

Bruker–Nonius Kappa CCD area-detector diffractometer

Absorption correction: Gaussian (Coppens, 1970 ▶) T min = 0.864, T max = 0.971

5966 measured reflections

1840 independent reflections

1455 reflections with I > 2σ(I)

R int = 0.110

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.146

S = 1.09

1840 reflections

109 parameters

H-atom parameters constrained

Δρmax = 0.44 e Å−3

Δρmin = −0.57 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶)and DENZO (Otwin­owski & Minor, 1997 ▶); cell refinement: DIRAX/LSQ (Duisenberg, 1992) ▶); data reduction: EvalCCD (Duisenberg, 1992) ▶); 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.

Crystal structure: contains datablocks I. DOI: 10.1107/S1600536808029541/hk2533sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808029541/hk2533Isup2.hkl

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

C8H6Cl2O2	Z = 2
Mr = 205.03	F(000) = 208
Triclinic, P1	Dx = 1.643 Mg m−3
Hall symbol: -P 1	Melting point: 319(2) K
a = 3.8452 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.0158 (4) Å	Cell parameters from 6024 reflections
c = 15.851 (1) Å	θ = 1–27.5°
α = 77.189 (6)°	µ = 0.73 mm−1
β = 89.130 (7)°	T = 150 K
γ = 83.741 (5)°	Needle, colorless
V = 414.46 (5) Å3	0.68 × 0.11 × 0.06 mm

Bruker–Nonius KappaCCD area-detector diffractometer	1840 independent reflections
Radiation source: fine-focus sealed tube	1455 reflections with I > 2σ(I)
graphite	Rint = 0.110
Detector resolution: 9.091 pixels mm-1	θmax = 27.5°, θmin = 2.6°
φ and ω scans	h = −4→4
Absorption correction: gaussian (Coppens, 1970)	k = −9→8
Tmin = 0.864, Tmax = 0.971	l = −20→20
5966 measured reflections

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.146	H-atom parameters constrained
S = 1.10	w = 1/[σ2(Fo2) + (0.0527P)2 + 0.5264P] where P = (Fo2 + 2Fc2)/3
1840 reflections	(Δ/σ)max < 0.001
109 parameters	Δρmax = 0.44 e Å−3
0 restraints	Δρmin = −0.57 e Å−3

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.

	x	y	z	Uiso*/Ueq
Cl1	0.6965 (2)	0.52269 (12)	0.70713 (5)	0.0309 (2)
Cl2	1.3585 (2)	−0.28182 (13)	0.92310 (5)	0.0361 (3)
O1	0.6439 (7)	−0.0150 (4)	0.62680 (14)	0.0347 (6)
O2	0.8542 (6)	0.2744 (4)	0.57949 (13)	0.0288 (5)
C1	0.9066 (8)	0.1286 (5)	0.72871 (18)	0.0220 (6)
C2	0.8841 (8)	0.2952 (5)	0.76262 (19)	0.0235 (6)
C3	1.0100 (9)	0.2857 (5)	0.8458 (2)	0.0278 (7)
H3	0.9954	0.3983	0.8680	0.033*
C4	1.1574 (9)	0.1080 (5)	0.89485 (19)	0.0286 (7)
H4	1.2435	0.1006	0.9501	0.034*
C5	1.1755 (8)	−0.0580 (5)	0.8613 (2)	0.0257 (7)
C6	1.0489 (8)	−0.0510 (5)	0.77933 (19)	0.0245 (6)
H6	1.0581	−0.1648	0.7581	0.029*
C7	0.7825 (8)	0.1206 (5)	0.64006 (18)	0.0229 (6)
C8	0.7421 (9)	0.2749 (5)	0.49289 (19)	0.0294 (7)
H8A	0.8509	0.1593	0.4761	0.035*
H8B	0.8089	0.3898	0.4536	0.035*
H8C	0.4924	0.2757	0.4914	0.035*

	U11	U22	U33	U12	U13	U23
Cl1	0.0411 (5)	0.0249 (4)	0.0250 (4)	0.0029 (3)	−0.0044 (3)	−0.0047 (3)
Cl2	0.0429 (5)	0.0328 (5)	0.0276 (4)	0.0027 (4)	−0.0115 (3)	0.0014 (3)
O1	0.0496 (16)	0.0344 (14)	0.0231 (11)	−0.0124 (11)	−0.0066 (10)	−0.0089 (10)
O2	0.0368 (13)	0.0354 (13)	0.0137 (10)	−0.0082 (10)	−0.0056 (8)	−0.0017 (9)
C1	0.0214 (15)	0.0287 (16)	0.0156 (13)	−0.0036 (12)	−0.0005 (10)	−0.0039 (11)
C2	0.0233 (15)	0.0256 (16)	0.0205 (14)	−0.0043 (12)	−0.0010 (11)	−0.0021 (12)
C3	0.0331 (18)	0.0295 (18)	0.0230 (15)	−0.0050 (13)	−0.0007 (12)	−0.0096 (13)
C4	0.0336 (18)	0.0348 (18)	0.0172 (14)	−0.0055 (14)	−0.0045 (12)	−0.0042 (12)
C5	0.0233 (16)	0.0303 (17)	0.0206 (14)	−0.0028 (12)	−0.0014 (11)	0.0003 (12)
C6	0.0302 (17)	0.0236 (16)	0.0205 (14)	−0.0008 (12)	−0.0026 (11)	−0.0073 (12)
C7	0.0257 (15)	0.0265 (16)	0.0166 (13)	0.0004 (12)	−0.0013 (11)	−0.0062 (11)
C8	0.0367 (19)	0.0368 (19)	0.0141 (13)	0.0003 (14)	−0.0047 (12)	−0.0061 (12)

Cl1—C2	1.728 (3)	C3—H3	0.9300
Cl2—C5	1.737 (3)	C4—C3	1.382 (5)
O1—C7	1.199 (4)	C4—C5	1.378 (5)
O2—C7	1.326 (4)	C4—H4	0.9300
O2—C8	1.444 (3)	C5—C6	1.384 (4)
C1—C2	1.385 (5)	C6—H6	0.9301
C1—C6	1.395 (4)	C8—H8A	0.9600
C1—C7	1.505 (4)	C8—H8B	0.9600
C2—C3	1.396 (4)	C8—H8C	0.9600
C7—O2—C8	115.5 (3)	C4—C5—Cl2	119.7 (2)
C2—C1—C6	119.3 (3)	C6—C5—Cl2	118.9 (3)
C2—C1—C7	125.6 (3)	C5—C6—C1	119.3 (3)
C6—C1—C7	115.1 (3)	C5—C6—H6	120.4
C1—C2—Cl1	123.1 (2)	C1—C6—H6	120.2
C1—C2—C3	120.7 (3)	O1—C7—O2	124.7 (3)
C3—C2—Cl1	116.3 (3)	O1—C7—C1	122.4 (3)
C4—C3—C2	119.7 (3)	O2—C7—C1	112.9 (3)
C4—C3—H3	120.1	O2—C8—H8A	109.4
C2—C3—H3	120.3	O2—C8—H8B	109.5
C5—C4—C3	119.5 (3)	H8A—C8—H8B	109.5
C5—C4—H4	120.3	O2—C8—H8C	109.5
C3—C4—H4	120.2	H8A—C8—H8C	109.5
C4—C5—C6	121.4 (3)	H8B—C8—H8C	109.5