2,4-Dichloro-phenyl 4-bromo-benzene-sulfonate.

In the title mol-ecule, C(12)H(7)BrCl(2)O(3)S, the dihedral angle between the two benzene rings is 55.18 (5)°. The notable inter-molecular contacts include C-H⋯O and π-π inter-actions [centroid-centroid distances = 4.037 (1) and 3.349 (1) Å].

Related literature

For a detailed account of the mol­ecular and supra­molecular architectures of aromatic sulfonates, see Vembu et al. (2007 ▶). For a general background to aromatic sulfonates, see: Yachi et al. (1989 ▶): Spungin et al. (1992 ▶); Tharakan et al. (1992 ▶); Alford et al. (1991 ▶); Jiang et al. (1990 ▶); Narayanan & Krakow (1983 ▶). For the criteria to describe C—H⋯O inter­actions, see: Desiraju & Steiner, (1999 ▶) and for the classification of aromatic stacking inter­actions, see: Spek (2009 ▶).

Experimental

Crystal data

C12H7BrCl2O3S

M = 382.05

Triclinic,

a = 7.2955 (10) Å

b = 8.3955 (11) Å

c = 11.1251 (15) Å

α = 95.737 (8)°

β = 98.645 (7)°

γ = 96.231 (8)°

V = 664.98 (15) Å3

Z = 2

Mo Kα radiation

μ = 3.65 mm−1

T = 90 K

0.17 × 0.10 × 0.07 mm

Data collection

Nonius KappaCCD diffractometer with Oxford Cryostream

Absorption correction: multi-scan (HKL SCALEPACK; Otwinowski & Minor 1997 ▶) T min = 0.576, T max = 0.784

18308 measured reflections

4745 independent reflections

4091 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.074

S = 1.05

4745 reflections

200 parameters

All H-atom parameters refined

Δρmax = 0.42 e Å−3

Δρmin = −0.76 e Å−3

Data collection: COLLECT (Nonius, 2000 ▶); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809042950/om2286sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809042950/om2286Isup2.hkl

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

C12H7BrCl2O3S	Z = 2
Mr = 382.05	F(000) = 376
Triclinic, P1	Dx = 1.908 Mg m−3
Hall symbol: -P 1	Melting point: 398 K
a = 7.2955 (10) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.3955 (11) Å	Cell parameters from 4109 reflections
c = 11.1251 (15) Å	θ = 2.5–33.6°
α = 95.737 (8)°	µ = 3.65 mm−1
β = 98.645 (7)°	T = 90 K
γ = 96.231 (8)°	Prism, colorless
V = 664.98 (15) Å3	0.17 × 0.10 × 0.07 mm

Nonius KappaCCD diffractometer with Oxford Cryostream	4745 independent reflections
Radiation source: fine-focus sealed tube	4091 reflections with I > 2σ(I)
graphite	Rint = 0.025
ω scans with κ offsets	θmax = 33.5°, θmin = 2.9°
Absorption correction: multi-scan (HKLSCALEPACK; Otwinowski & Minor 1997)	h = −10→11
Tmin = 0.576, Tmax = 0.784	k = −12→12
18308 measured reflections	l = −16→17

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)] = 0.031	Hydrogen site location: difference Fourier map
wR(F2) = 0.074	All H-atom parameters refined
S = 1.05	w = 1/[σ2(Fo2) + (0.0284P)2 + 0.6284P] where P = (Fo2 + 2Fc2)/3
4745 reflections	(Δ/σ)max = 0.001
200 parameters	Δρmax = 0.42 e Å−3
0 restraints	Δρmin = −0.76 e Å−3

Geometry. All su's (except the su in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell su's are taken into account individually in the estimation of su's in distances, angles and torsion angles; correlations between su's in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell su's is used for estimating su'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
Br1	0.64701 (3)	0.17437 (2)	0.428948 (18)	0.01931 (6)
Cl1	0.02233 (6)	0.03498 (5)	0.69619 (4)	0.01838 (9)
Cl2	0.36290 (6)	−0.08990 (6)	1.13426 (5)	0.02035 (10)
S1	0.14495 (6)	0.51012 (5)	0.77797 (4)	0.01350 (8)
O1	0.26445 (19)	0.59769 (16)	0.88237 (13)	0.0180 (3)
O2	0.00437 (19)	0.58520 (17)	0.70897 (13)	0.0193 (3)
O3	0.02261 (17)	0.36107 (15)	0.82191 (12)	0.0136 (2)
C1	0.4977 (2)	0.2748 (2)	0.53130 (17)	0.0139 (3)
C2	0.5760 (2)	0.3301 (2)	0.65200 (18)	0.0161 (3)
C3	0.4664 (3)	0.4019 (2)	0.72856 (17)	0.0154 (3)
C4	0.2818 (2)	0.4176 (2)	0.68176 (16)	0.0129 (3)
C5	0.2045 (2)	0.3631 (2)	0.56058 (17)	0.0150 (3)
C6	0.3137 (3)	0.2911 (2)	0.48443 (17)	0.0159 (3)
C7	0.1140 (2)	0.2578 (2)	0.89617 (16)	0.0125 (3)
C8	0.1862 (3)	0.3101 (2)	1.01796 (17)	0.0157 (3)
C9	0.2658 (3)	0.2032 (2)	1.09162 (17)	0.0169 (3)
C10	0.2681 (2)	0.0454 (2)	1.04188 (17)	0.0148 (3)
C11	0.1949 (2)	−0.0090 (2)	0.92034 (17)	0.0145 (3)
C12	0.1179 (2)	0.0995 (2)	0.84746 (16)	0.0129 (3)
H2	0.702 (4)	0.319 (3)	0.682 (2)	0.023 (6)*
H3	0.511 (4)	0.442 (3)	0.811 (2)	0.021 (6)*
H5	0.075 (4)	0.373 (3)	0.533 (2)	0.027 (7)*
H6	0.266 (3)	0.253 (3)	0.405 (2)	0.020 (6)*
H8	0.177 (3)	0.419 (3)	1.050 (2)	0.019 (6)*
H9	0.316 (4)	0.241 (3)	1.174 (3)	0.025 (7)*
H11	0.201 (3)	−0.113 (3)	0.889 (2)	0.014 (6)*

	U11	U22	U33	U12	U13	U23
Br1	0.02086 (9)	0.01838 (10)	0.02144 (10)	0.00506 (7)	0.01007 (7)	0.00289 (7)
Cl1	0.0235 (2)	0.0159 (2)	0.01452 (19)	0.00065 (16)	0.00259 (16)	−0.00138 (15)
Cl2	0.01585 (19)	0.0236 (2)	0.0246 (2)	0.00547 (16)	0.00383 (16)	0.01331 (18)
S1	0.01517 (18)	0.01071 (18)	0.01559 (19)	0.00379 (14)	0.00343 (15)	0.00253 (14)
O1	0.0223 (6)	0.0124 (6)	0.0186 (6)	0.0010 (5)	0.0036 (5)	−0.0010 (5)
O2	0.0210 (6)	0.0179 (7)	0.0223 (7)	0.0101 (5)	0.0054 (5)	0.0071 (5)
O3	0.0125 (5)	0.0132 (6)	0.0159 (6)	0.0027 (4)	0.0023 (4)	0.0044 (5)
C1	0.0160 (7)	0.0112 (7)	0.0168 (8)	0.0032 (6)	0.0072 (6)	0.0034 (6)
C2	0.0134 (7)	0.0167 (8)	0.0192 (8)	0.0030 (6)	0.0024 (6)	0.0054 (7)
C3	0.0146 (7)	0.0158 (8)	0.0150 (8)	0.0010 (6)	0.0002 (6)	0.0024 (6)
C4	0.0139 (7)	0.0104 (7)	0.0151 (8)	0.0026 (6)	0.0035 (6)	0.0021 (6)
C5	0.0136 (7)	0.0158 (8)	0.0151 (8)	0.0022 (6)	0.0002 (6)	0.0024 (6)
C6	0.0167 (8)	0.0167 (8)	0.0138 (8)	0.0010 (6)	0.0013 (6)	0.0029 (6)
C7	0.0123 (7)	0.0120 (7)	0.0146 (7)	0.0025 (6)	0.0043 (6)	0.0035 (6)
C8	0.0185 (8)	0.0141 (8)	0.0145 (8)	0.0021 (6)	0.0031 (6)	0.0008 (6)
C9	0.0166 (8)	0.0188 (9)	0.0148 (8)	0.0004 (7)	0.0017 (6)	0.0028 (7)
C10	0.0110 (7)	0.0163 (8)	0.0191 (8)	0.0032 (6)	0.0038 (6)	0.0088 (6)
C11	0.0136 (7)	0.0124 (8)	0.0192 (8)	0.0033 (6)	0.0053 (6)	0.0040 (6)
C12	0.0123 (7)	0.0137 (8)	0.0128 (7)	0.0010 (6)	0.0035 (6)	0.0005 (6)

Br1—C1	1.8909 (17)	C4—C5	1.392 (2)
Cl1—C12	1.7306 (18)	C5—C6	1.387 (3)
Cl2—C10	1.7361 (18)	C5—H5	0.96 (3)
S1—O1	1.4267 (15)	C6—H6	0.91 (3)
S1—O2	1.4279 (14)	C7—C8	1.386 (2)
S1—O3	1.6163 (13)	C7—C12	1.390 (2)
S1—C4	1.7520 (18)	C8—C9	1.390 (3)
O3—C7	1.407 (2)	C8—H8	0.96 (3)
C1—C2	1.390 (3)	C9—C10	1.387 (3)
C1—C6	1.391 (3)	C9—H9	0.94 (3)
C2—C3	1.391 (3)	C10—C11	1.389 (3)
C2—H2	0.95 (3)	C11—C12	1.387 (2)
C3—C4	1.394 (2)	C11—H11	0.91 (2)
C3—H3	0.94 (3)
O1—S1—O2	120.61 (9)	C5—C6—C1	119.11 (17)
O1—S1—O3	108.71 (8)	C5—C6—H6	120.8 (16)
O2—S1—O3	102.04 (8)	C1—C6—H6	120.0 (16)
O1—S1—C4	109.04 (8)	C8—C7—C12	120.82 (16)
O2—S1—C4	110.81 (9)	C8—C7—O3	120.41 (16)
O3—S1—C4	104.20 (8)	C12—C7—O3	118.60 (16)
C7—O3—S1	119.14 (11)	C7—C8—C9	119.49 (17)
C2—C1—C6	121.93 (16)	C7—C8—H8	119.2 (15)
C2—C1—Br1	118.56 (13)	C9—C8—H8	121.3 (15)
C6—C1—Br1	119.51 (14)	C10—C9—C8	119.06 (17)
C1—C2—C3	119.00 (16)	C10—C9—H9	122.2 (16)
C1—C2—H2	120.7 (16)	C8—C9—H9	118.7 (17)
C3—C2—H2	120.3 (16)	C9—C10—C11	122.05 (17)
C2—C3—C4	119.06 (17)	C9—C10—Cl2	119.28 (15)
C2—C3—H3	123.1 (16)	C11—C10—Cl2	118.66 (14)
C4—C3—H3	117.8 (16)	C12—C11—C10	118.29 (17)
C5—C4—C3	121.71 (16)	C12—C11—H11	121.4 (15)
C5—C4—S1	119.34 (13)	C10—C11—H11	120.2 (15)
C3—C4—S1	118.94 (14)	C11—C12—C7	120.28 (16)
C6—C5—C4	119.18 (16)	C11—C12—Cl1	119.48 (14)
C6—C5—H5	121.9 (17)	C7—C12—Cl1	120.22 (14)
C4—C5—H5	118.9 (16)
O1—S1—O3—C7	−50.31 (14)	C2—C1—C6—C5	−0.6 (3)
O2—S1—O3—C7	−178.76 (13)	Br1—C1—C6—C5	179.19 (14)
C4—S1—O3—C7	65.86 (14)	S1—O3—C7—C8	72.63 (19)
C6—C1—C2—C3	0.8 (3)	S1—O3—C7—C12	−112.06 (16)
Br1—C1—C2—C3	−179.02 (14)	C12—C7—C8—C9	0.9 (3)
C1—C2—C3—C4	−0.5 (3)	O3—C7—C8—C9	176.11 (16)
C2—C3—C4—C5	0.0 (3)	C7—C8—C9—C10	−1.1 (3)
C2—C3—C4—S1	−179.30 (14)	C8—C9—C10—C11	0.6 (3)
O1—S1—C4—C5	−162.54 (14)	C8—C9—C10—Cl2	−178.65 (14)
O2—S1—C4—C5	−27.52 (17)	C9—C10—C11—C12	0.2 (3)
O3—S1—C4—C5	81.53 (15)	Cl2—C10—C11—C12	179.41 (13)
O1—S1—C4—C3	16.82 (17)	C10—C11—C12—C7	−0.4 (3)
O2—S1—C4—C3	151.84 (15)	C10—C11—C12—Cl1	−179.04 (13)
O3—S1—C4—C3	−99.11 (15)	C8—C7—C12—C11	−0.1 (3)
C3—C4—C5—C6	0.1 (3)	O3—C7—C12—C11	−175.43 (15)
S1—C4—C5—C6	179.47 (14)	C8—C7—C12—Cl1	178.50 (14)
C4—C5—C6—C1	0.2 (3)	O3—C7—C12—Cl1	3.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1	0.94 (3)	2.51 (3)	2.919 (2)	106.2 (18)
C2—H2···O3i	0.95 (3)	2.58 (3)	3.482 (2)	160 (2)
C11—H11···O1ii	0.91 (2)	2.52 (2)	3.390 (2)	160 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O3i	0.95 (3)	2.58 (3)	3.482 (2)	160 (2)
C11—H11⋯O1ii	0.91 (2)	2.52 (2)	3.390 (2)	160 (2)

Symmetry codes: (i) ; (ii) .