Dimethyl 4,5-dichlorobenzene-1,2-dicarboxyl-ate.

In the title compound, C(10)H(8)Cl(2)O(4), the two Cl atoms and one of the meth-oxy-carbonyl groups are almost coplanar [maxi-mum derivation = 0.035 (2) Å] with the benzene plane, and the other meth-oxy-carbonyl group exhibits an almost orthogonal disposition relative to the benzene plane, with a dihedral angle of 84.82 (3)° between the planes. In the crystal, the molecules are connected into a chain propagating along the [011] direction through nonclassical C-H⋯O hydrogen bonds.

Related literature

For the chemical properties and structural nature nature of some related benzene­carboxyl­ate derivatives, see: Galešić et al. (1984 ▶); Liang et al. (2004 ▶); Mallinson et al. (2003 ▶); Rauf et al. (2008 ▶).

Experimental

Crystal data

C10H8Cl2O4

M = 263.06

Triclinic,

a = 7.1906 (14) Å

b = 7.8410 (17) Å

c = 10.6205 (15) Å

α = 97.779 (15)°

β = 109.040 (15)°

γ = 91.864 (18)°

V = 558.95 (19) Å3

Z = 2

Mo Kα radiation

μ = 0.58 mm−1

T = 295 K

0.24 × 0.20 × 0.18 mm

Data collection

Bruker SMART 1000 CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.871, T max = 0.902

3362 measured reflections

1966 independent reflections

1663 reflections with I > 2σ(I)

R int = 0.010

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.092

S = 1.03

1966 reflections

147 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.24 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAINT; 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: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812007167/rk2334sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812007167/rk2334Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812007167/rk2334Isup3.cml

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

C10H8Cl2O4	Z = 2
Mr = 263.06	F(000) = 268
Triclinic, P1	Dx = 1.563 Mg m−3
Hall symbol: -P 1	Melting point: 389 K
a = 7.1906 (14) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.8410 (17) Å	Cell parameters from 1973 reflections
c = 10.6205 (15) Å	θ = 2.4–25.0°
α = 97.779 (15)°	µ = 0.58 mm−1
β = 109.040 (15)°	T = 295 K
γ = 91.864 (18)°	Block, colourless
V = 558.95 (19) Å3	0.24 × 0.20 × 0.18 mm

Bruker SMART 1000 CCD diffractometer	1966 independent reflections
Radiation source: fine-focus sealed tube	1663 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.010
φ and ω scans	θmax = 25.0°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→8
Tmin = 0.871, Tmax = 0.902	k = −9→8
3362 measured reflections	l = −12→12

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.092	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0449P)2 + 0.1781P] where P = (Fo2 + 2Fc2)/3
1966 reflections	(Δ/σ)max < 0.001
147 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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	0.31371 (9)	0.97739 (8)	0.82726 (5)	0.0629 (2)
Cl2	0.25088 (11)	0.57862 (8)	0.71088 (6)	0.0693 (2)
O1	0.3423 (2)	0.70631 (19)	0.21566 (13)	0.0517 (4)
O3	0.2024 (2)	1.05587 (17)	0.22604 (14)	0.0524 (4)
C7	0.1745 (3)	0.7231 (2)	0.24061 (19)	0.0404 (4)
C9	0.2309 (3)	1.1128 (2)	0.3543 (2)	0.0414 (4)
C1	0.2123 (3)	0.7964 (2)	0.38630 (18)	0.0365 (4)
C6	0.2187 (3)	0.6771 (2)	0.47290 (19)	0.0449 (5)
H6	0.2027	0.5596	0.4397	0.054*
C3	0.2674 (3)	1.0250 (2)	0.57299 (19)	0.0401 (4)
H7	0.2835	1.1423	0.6069	0.048*
C2	0.2367 (2)	0.9725 (2)	0.43690 (18)	0.0349 (4)
C4	0.2743 (3)	0.9063 (3)	0.65837 (19)	0.0404 (4)
C5	0.2487 (3)	0.7316 (2)	0.60792 (19)	0.0431 (5)
O2	0.0140 (2)	0.6798 (2)	0.16088 (15)	0.0648 (4)
O4	0.2507 (4)	1.26184 (19)	0.39955 (19)	0.0862 (6)
C10	0.1877 (4)	1.1857 (3)	0.1392 (3)	0.0655 (7)
H13A	0.1488	1.1307	0.0470	0.098*
H13C	0.3134	1.2499	0.1630	0.098*
H13B	0.0910	1.2628	0.1499	0.098*
C8	0.3252 (4)	0.6420 (3)	0.0777 (2)	0.0654 (7)
H14C	0.2624	0.7232	0.0206	0.098*
H14A	0.2476	0.5331	0.0491	0.098*
H14B	0.4544	0.6271	0.0720	0.098*

	U11	U22	U33	U12	U13	U23
Cl1	0.0775 (4)	0.0733 (4)	0.0381 (3)	−0.0010 (3)	0.0256 (3)	−0.0048 (3)
Cl2	0.1004 (5)	0.0595 (4)	0.0460 (3)	−0.0028 (3)	0.0175 (3)	0.0212 (3)
O1	0.0606 (10)	0.0574 (9)	0.0324 (7)	0.0079 (7)	0.0121 (7)	−0.0017 (6)
O3	0.0733 (10)	0.0391 (8)	0.0445 (8)	0.0031 (7)	0.0171 (7)	0.0124 (6)
C7	0.0532 (12)	0.0281 (9)	0.0347 (10)	−0.0003 (8)	0.0077 (9)	0.0049 (7)
C9	0.0407 (11)	0.0328 (10)	0.0472 (11)	0.0020 (8)	0.0104 (9)	0.0056 (8)
C1	0.0370 (10)	0.0335 (9)	0.0339 (10)	0.0009 (7)	0.0062 (8)	0.0027 (7)
C6	0.0580 (13)	0.0320 (10)	0.0392 (11)	−0.0003 (8)	0.0104 (9)	0.0028 (8)
C3	0.0380 (10)	0.0352 (10)	0.0434 (11)	0.0014 (8)	0.0124 (8)	−0.0028 (8)
C2	0.0299 (9)	0.0330 (9)	0.0388 (10)	0.0016 (7)	0.0083 (8)	0.0034 (7)
C4	0.0346 (10)	0.0500 (11)	0.0343 (10)	0.0003 (8)	0.0112 (8)	0.0007 (8)
C5	0.0474 (11)	0.0428 (11)	0.0373 (10)	0.0000 (8)	0.0109 (9)	0.0089 (8)
O2	0.0618 (10)	0.0745 (11)	0.0412 (9)	−0.0148 (8)	0.0007 (8)	−0.0018 (8)
O4	0.159 (2)	0.0288 (8)	0.0697 (12)	0.0046 (9)	0.0378 (12)	0.0052 (8)
C10	0.0815 (17)	0.0585 (14)	0.0626 (15)	0.0099 (12)	0.0233 (13)	0.0313 (12)
C8	0.0928 (19)	0.0670 (15)	0.0366 (11)	0.0110 (13)	0.0243 (12)	0.0006 (10)

Cl1—C4	1.7308 (19)	C6—C5	1.383 (3)
Cl2—C5	1.7260 (19)	C6—H6	0.9300
O1—C7	1.324 (2)	C3—C4	1.376 (3)
O1—C8	1.447 (2)	C3—C2	1.390 (3)
O3—C9	1.321 (2)	C3—H7	0.9300
O3—C10	1.448 (2)	C4—C5	1.385 (3)
C7—O2	1.193 (2)	C10—H13A	0.9600
C7—C1	1.508 (3)	C10—H13C	0.9600
C9—O4	1.187 (2)	C10—H13B	0.9600
C9—C2	1.490 (3)	C8—H14C	0.9600
C1—C6	1.390 (3)	C8—H14A	0.9600
C1—C2	1.396 (3)	C8—H14B	0.9600
C7—O1—C8	116.24 (17)	C1—C2—C9	124.47 (17)
C9—O3—C10	116.45 (16)	C3—C4—C5	119.57 (17)
O2—C7—O1	125.13 (18)	C3—C4—Cl1	119.55 (15)
O2—C7—C1	123.77 (19)	C5—C4—Cl1	120.87 (15)
O1—C7—C1	111.03 (16)	C6—C5—C4	120.08 (17)
O4—C9—O3	123.07 (18)	C6—C5—Cl2	118.90 (15)
O4—C9—C2	123.22 (19)	C4—C5—Cl2	121.02 (15)
O3—C9—C2	113.71 (15)	O3—C10—H13A	109.5
C6—C1—C2	119.35 (17)	O3—C10—H13C	109.5
C6—C1—C7	116.17 (16)	H13A—C10—H13C	109.5
C2—C1—C7	124.47 (16)	O3—C10—H13B	109.5
C5—C6—C1	120.58 (17)	H13A—C10—H13B	109.5
C5—C6—H6	119.7	H13C—C10—H13B	109.5
C1—C6—H6	119.7	O1—C8—H14C	109.5
C4—C3—C2	121.09 (17)	O1—C8—H14A	109.5
C4—C3—H7	119.5	H14C—C8—H14A	109.5
C2—C3—H7	119.5	O1—C8—H14B	109.5
C3—C2—C1	119.31 (17)	H14C—C8—H14B	109.5
C3—C2—C9	116.21 (16)	H14A—C8—H14B	109.5

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O4i	0.93	2.37	3.278 (2)	164

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O4i	0.93	2.37	3.278 (2)	164

Symmetry code: (i) .