3,6-Dichloro-catechol.

The title compound, C(6)H(4)Cl(2)O(2), exhibits a two-dimensional supra-molecular hydrogen-bonded network and forms a three-dimensional network supra-molecular structure via hydrogen bonds and π-π stacking of benzene rings. The π-π inter-actions are between the benzene rings of centrosymmetrically related mol-ecules, with centroid-centroid distances of 3.7676 (13) and 3.7107 (13) Å.

Related literature

For related literature, see: Haigler et al. (1988 ▶); Kirsh & Stan (1994 ▶); Nishizawa & Satoh (1975a ▶,b ▶); Sander et al. (1991 ▶); Schraa et al. (1986 ▶); Spiess et al. (1995 ▶); Spain et al. (1989 ▶).

Experimental

Crystal data

C6H4Cl2O2

M = 178.99

Monoclinic,

a = 7.4411 (7) Å

b = 10.1283 (10) Å

c = 10.6448 (8) Å

β = 119.903 (5)°

V = 695.45 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.86 mm−1

T = 296 K

0.36 × 0.17 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1997 ▶) T min = 0.748, T max = 0.882

3531 measured reflections

1243 independent reflections

1117 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.118

S = 1.01

1243 reflections

93 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.34 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SMART; data reduction: SAINT (Bruker, 1997 ▶); 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 datablocks global, I. DOI: 10.1107/S1600536808025014/bq2078sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808025014/bq2078Isup2.hkl

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

C6H4Cl2O2	F000 = 360
Mr = 178.99	Dx = 1.710 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2193 reflections
a = 7.4411 (7) Å	θ = 2.9–26.4º
b = 10.1283 (10) Å	µ = 0.86 mm−1
c = 10.6448 (8) Å	T = 296 K
β = 119.903 (5)º	Block, colorless
V = 695.45 (11) Å3	0.36 × 0.17 × 0.15 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	1243 independent reflections
Radiation source: fine-focus sealed tube	1117 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.017
T = 296 K	θmax = 25.2º
φ and ω scans	θmin = 3.0º
Absorption correction: multi-scan(SADABS; Bruker, 1997)	h = −8→8
Tmin = 0.748, Tmax = 0.882	k = −9→12
3531 measured reflections	l = −12→12

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)] = 0.030	H-atom parameters constrained
wR(F2) = 0.118	w = 1/[σ2(Fo2) + (0.01P)2] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max = 0.001
1243 reflections	Δρmax = 0.18 e Å−3
93 parameters	Δρmin = −0.34 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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 takeninto account individually in the estimation of e.s.d.'s in distances, anglesand torsion angles; correlations between e.s.d.'s in cell parameters are onlyused 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 andgoodness of fit S are based on F2, conventional R-factors R are basedon F, with F set to zero for negative F2. The threshold expression ofF2 > σ(F2) is used only for calculating R-factors(gt) etc. and isnot relevant to the choice of reflections for refinement. R-factors basedon 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	0.84969 (7)	1.04043 (6)	0.81747 (4)	0.0483 (3)
Cl2	0.64593 (7)	0.99288 (7)	0.17713 (4)	0.0529 (3)
O1	0.8451 (2)	0.79625 (12)	0.66807 (12)	0.0487 (4)
H1	0.8578	0.7331	0.6249	0.073*
O2	0.7560 (2)	0.76889 (12)	0.39645 (12)	0.0490 (4)
H2	0.7570	0.7708	0.3198	0.074*
C1	0.7904 (3)	1.02895 (16)	0.63843 (18)	0.0344 (4)
C2	0.7954 (2)	0.90633 (16)	0.58289 (15)	0.0335 (4)
C3	0.7515 (2)	0.89485 (16)	0.44037 (17)	0.0330 (4)
C4	0.7012 (3)	1.00694 (18)	0.35485 (17)	0.0356 (4)
C5	0.6955 (3)	1.13066 (18)	0.41095 (17)	0.0433 (4)
H5	0.6619	1.2056	0.3530	0.052*
C6	0.7397 (3)	1.14090 (18)	0.55181 (19)	0.0415 (4)
H6	0.7359	1.2230	0.5896	0.050*

	U11	U22	U33	U12	U13	U23
Cl1	0.0647 (4)	0.0507 (4)	0.0356 (4)	−0.00327 (18)	0.0296 (3)	−0.00797 (16)
Cl2	0.0633 (4)	0.0666 (5)	0.0307 (4)	0.0071 (2)	0.0248 (3)	0.00907 (18)
O1	0.0832 (10)	0.0343 (7)	0.0401 (7)	0.0122 (6)	0.0393 (7)	0.0089 (5)
O2	0.0835 (10)	0.0351 (7)	0.0414 (7)	−0.0021 (6)	0.0409 (7)	−0.0039 (5)
C1	0.0382 (9)	0.0370 (9)	0.0307 (8)	−0.0029 (6)	0.0192 (7)	−0.0042 (6)
C2	0.0394 (8)	0.0323 (9)	0.0317 (8)	0.0010 (7)	0.0199 (7)	0.0053 (6)
C3	0.0373 (8)	0.0334 (9)	0.0298 (7)	−0.0025 (6)	0.0177 (6)	−0.0020 (6)
C4	0.0360 (9)	0.0445 (10)	0.0276 (8)	−0.0007 (7)	0.0169 (7)	0.0042 (7)
C5	0.0488 (10)	0.0354 (9)	0.0450 (9)	0.0037 (7)	0.0230 (8)	0.0100 (7)
C6	0.0508 (10)	0.0309 (9)	0.0429 (8)	0.0009 (7)	0.0234 (7)	−0.0003 (7)

O1—H1	0.8200	C3—O2	1.365 (2)
O2—H2	0.8200	C3—C4	1.385 (2)
C1—C2	1.384 (2)	C4—C5	1.398 (2)
C1—C6	1.390 (2)	C4—Cl2	1.7299 (16)
C1—Cl1	1.7326 (17)	C5—C6	1.369 (3)
C2—O1	1.3666 (18)	C5—H5	0.9300
C2—C3	1.388 (2)	C6—H6	0.9300
O1—C2—C1	120.31 (13)	C3—C4—C5	120.65 (15)
O1—C2—C3	119.68 (14)	C3—C4—Cl2	119.36 (13)
O2—C3—C4	125.85 (14)	C4—C3—C2	119.27 (15)
O2—C3—C2	114.84 (14)	C4—C5—H5	120.2
C1—C2—C3	120.02 (14)	C5—C4—Cl2	119.98 (13)
C1—C6—H6	119.9	C5—C6—C1	120.16 (16)
C2—O1—H1	109.5	C5—C6—H6	119.9
C2—C1—C6	120.32 (15)	C6—C5—C4	119.59 (15)
C2—C1—Cl1	118.94 (12)	C6—C1—Cl1	120.75 (13)
C3—O2—H2	109.5	C6—C5—H5	120.2
Cl1—C1—C2—O1	0.4 (2)	C1—C2—C3—C4	−0.5 (2)
Cl1—C1—C2—C3	−179.06 (12)	C2—C1—C6—C5	−0.3 (3)
Cl1—C1—C6—C5	179.23 (13)	C2—C3—C4—C5	0.3 (2)
Cl2—C4—C5—C6	−179.92 (13)	C2—C3—C4—Cl2	−179.90 (12)
O1—C2—C3—O2	2.1 (2)	C3—C4—C5—C6	−0.1 (3)
O1—C2—C3—C4	179.98 (15)	C4—C5—C6—C1	0.2 (3)
O2—C3—C4—C5	177.97 (16)	C6—C1—C2—O1	−179.97 (15)
O2—C3—C4—Cl2	−2.3 (2)	C6—C1—C2—C3	0.5 (2)
C1—C2—C3—O2	−178.41 (15)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.82	2.19	2.6391 (17)	115
O1—H1···Cl1i	0.82	2.76	3.3980 (16)	137
O2—H2···Cl2	0.82	2.61	3.0597 (13)	116
O2—H2···O1ii	0.82	2.13	2.8969 (19)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2	0.82	2.19	2.6391 (17)	115
O1—H1⋯Cl1i	0.82	2.76	3.3980 (16)	137
O2—H2⋯Cl2	0.82	2.61	3.0597 (13)	116
O2—H2⋯O1ii	0.82	2.13	2.8969 (19)	155

Symmetry codes: (i) ; (ii) .