Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680301208X/ob6251sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680301208X/ob6251Isup2.hkl |
CCDC reference: 217450
4-Toluenesulfonyl chloride (4.7 mmol), dissolved in acetone (4 ml), was added dropwise to 2,4-dichlorophenol (5.5 mol) in aqueous NaOH (2.5 ml, 10%) with constant shaking. The precipitated title compound (3.3 mmol, yield 70%) was filtered off and recrystallized from a 1:1 mixture of petroleum ether and acetone.
All hydrogen atoms were located from a difference Fourier map and their positional coordinates and isotropic displacement paramaters were refined. The C—H bond lengths are in the range 0.91 (3)–0.97 (2) Å, the H—C—H angles for the methyl group are in the range 103 (2)–110 (2)° and the C—C—H angles for the aromatic rings are in the range 117.4 (1)–122.2 (1)°.
Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
C13H10Cl2O3S | F(000) = 324 |
Mr = 317.17 | Dx = 1.598 Mg m−3 |
Triclinic, P1 | Melting point = 373–375 K |
a = 7.7314 (11) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.3724 (11) Å | Cell parameters from 7298 reflections |
c = 10.7055 (15) Å | θ = 2.5–28.4° |
α = 99.079 (2)° | µ = 0.65 mm−1 |
β = 96.119 (2)° | T = 100 K |
γ = 103.134 (2)° | Block, colorless |
V = 659.04 (16) Å3 | 0.55 × 0.50 × 0.40 mm |
Z = 2 |
CCD area detector diffractometer | 3074 independent reflections |
Radiation source: fine-focus sealed tube | 2954 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.015 |
ϕ and ω scans | θmax = 28.4°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −10→9 |
Tmin = 0.716, Tmax = 0.781 | k = −11→10 |
8295 measured reflections | l = −14→14 |
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)] = 0.028 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.077 | All H-atom parameters refined |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0378P)2 + 0.4025P] where P = (Fo2 + 2Fc2)/3 |
3074 reflections | (Δ/σ)max = 0.001 |
212 parameters | Δρmax = 0.39 e Å−3 |
0 restraints | Δρmin = −0.32 e Å−3 |
C13H10Cl2O3S | γ = 103.134 (2)° |
Mr = 317.17 | V = 659.04 (16) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.7314 (11) Å | Mo Kα radiation |
b = 8.3724 (11) Å | µ = 0.65 mm−1 |
c = 10.7055 (15) Å | T = 100 K |
α = 99.079 (2)° | 0.55 × 0.50 × 0.40 mm |
β = 96.119 (2)° |
CCD area detector diffractometer | 3074 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2954 reflections with I > 2σ(I) |
Tmin = 0.716, Tmax = 0.781 | Rint = 0.015 |
8295 measured reflections |
R[F2 > 2σ(F2)] = 0.028 | 0 restraints |
wR(F2) = 0.077 | All H-atom parameters refined |
S = 1.08 | Δρmax = 0.39 e Å−3 |
3074 reflections | Δρmin = −0.32 e Å−3 |
212 parameters |
Experimental. The Tmin and Tmax values obtained from the SIZE instruction are listed above. The absorption correction was applied using SADABS and it gives 0.901603 ratio of min/max transmission" |
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 | ||
S | 0.35514 (5) | 0.00280 (4) | 0.23813 (3) | 0.01748 (10) | |
Cl1 | 0.45681 (5) | 0.49434 (4) | 0.31856 (3) | 0.02440 (10) | |
Cl2 | 0.14177 (5) | 0.52405 (5) | −0.14652 (4) | 0.02600 (10) | |
O1 | 0.47889 (15) | −0.04614 (14) | 0.32349 (11) | 0.0250 (2) | |
O2 | 0.25961 (15) | −0.11069 (13) | 0.12540 (11) | 0.0236 (2) | |
O3 | 0.48113 (13) | 0.16079 (12) | 0.19492 (10) | 0.0174 (2) | |
C1 | −0.1690 (2) | 0.3051 (2) | 0.51223 (18) | 0.0267 (3) | |
C2 | −0.03703 (19) | 0.23010 (17) | 0.44474 (15) | 0.0193 (3) | |
C3 | 0.1225 (2) | 0.21731 (19) | 0.51221 (14) | 0.0205 (3) | |
C4 | 0.2440 (2) | 0.14659 (18) | 0.45074 (14) | 0.0194 (3) | |
C5 | 0.20369 (18) | 0.08855 (17) | 0.31954 (13) | 0.0162 (3) | |
C6 | 0.04635 (19) | 0.10076 (18) | 0.24933 (14) | 0.0184 (3) | |
C7 | −0.07293 (19) | 0.17108 (18) | 0.31323 (15) | 0.0198 (3) | |
C8 | 0.39860 (18) | 0.24500 (17) | 0.11238 (13) | 0.0157 (3) | |
C9 | 0.37926 (18) | 0.40343 (17) | 0.16049 (13) | 0.0165 (3) | |
C10 | 0.30044 (18) | 0.49065 (17) | 0.08087 (14) | 0.0183 (3) | |
C11 | 0.24333 (19) | 0.41690 (18) | −0.04656 (14) | 0.0187 (3) | |
C12 | 0.2659 (2) | 0.26087 (18) | −0.09650 (14) | 0.0206 (3) | |
C13 | 0.34456 (19) | 0.17467 (18) | −0.01564 (14) | 0.0185 (3) | |
H1A | −0.202 (4) | 0.387 (4) | 0.472 (3) | 0.069 (9)* | |
H1B | −0.273 (3) | 0.224 (3) | 0.519 (2) | 0.048 (7)* | |
H1C | −0.126 (4) | 0.354 (4) | 0.595 (3) | 0.066 (8)* | |
H3 | 0.152 (3) | 0.256 (3) | 0.602 (2) | 0.032 (5)* | |
H4 | 0.350 (3) | 0.138 (3) | 0.499 (2) | 0.032 (5)* | |
H6 | 0.022 (2) | 0.063 (2) | 0.1578 (18) | 0.017 (4)* | |
H7 | −0.180 (3) | 0.177 (3) | 0.268 (2) | 0.035 (5)* | |
H10 | 0.286 (3) | 0.599 (2) | 0.1125 (18) | 0.026 (5)* | |
H12 | 0.231 (3) | 0.214 (3) | −0.185 (2) | 0.029 (5)* | |
H13 | 0.356 (2) | 0.064 (2) | −0.0455 (18) | 0.021 (4)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S | 0.01871 (17) | 0.01458 (16) | 0.02211 (18) | 0.00756 (13) | 0.00526 (13) | 0.00569 (13) |
Cl1 | 0.0303 (2) | 0.02017 (18) | 0.02093 (18) | 0.00586 (14) | 0.00299 (14) | −0.00047 (13) |
Cl2 | 0.02321 (19) | 0.0284 (2) | 0.0309 (2) | 0.01036 (15) | 0.00224 (14) | 0.01456 (15) |
O1 | 0.0249 (5) | 0.0269 (6) | 0.0314 (6) | 0.0153 (5) | 0.0077 (5) | 0.0142 (5) |
O2 | 0.0281 (6) | 0.0143 (5) | 0.0279 (6) | 0.0052 (4) | 0.0072 (4) | 0.0007 (4) |
O3 | 0.0155 (4) | 0.0170 (5) | 0.0219 (5) | 0.0060 (4) | 0.0036 (4) | 0.0068 (4) |
C1 | 0.0238 (8) | 0.0249 (8) | 0.0340 (9) | 0.0093 (6) | 0.0108 (7) | 0.0042 (7) |
C2 | 0.0177 (7) | 0.0152 (6) | 0.0265 (7) | 0.0040 (5) | 0.0072 (5) | 0.0060 (5) |
C3 | 0.0220 (7) | 0.0214 (7) | 0.0180 (7) | 0.0048 (6) | 0.0037 (5) | 0.0037 (5) |
C4 | 0.0176 (7) | 0.0212 (7) | 0.0208 (7) | 0.0059 (5) | 0.0011 (5) | 0.0074 (5) |
C5 | 0.0158 (6) | 0.0141 (6) | 0.0201 (7) | 0.0046 (5) | 0.0043 (5) | 0.0045 (5) |
C6 | 0.0174 (6) | 0.0182 (6) | 0.0189 (7) | 0.0029 (5) | 0.0015 (5) | 0.0046 (5) |
C7 | 0.0146 (6) | 0.0208 (7) | 0.0252 (7) | 0.0050 (5) | 0.0016 (5) | 0.0076 (6) |
C8 | 0.0134 (6) | 0.0148 (6) | 0.0206 (7) | 0.0048 (5) | 0.0041 (5) | 0.0056 (5) |
C9 | 0.0153 (6) | 0.0158 (6) | 0.0181 (6) | 0.0029 (5) | 0.0049 (5) | 0.0016 (5) |
C10 | 0.0161 (6) | 0.0141 (6) | 0.0265 (7) | 0.0047 (5) | 0.0071 (5) | 0.0049 (5) |
C11 | 0.0144 (6) | 0.0190 (6) | 0.0250 (7) | 0.0048 (5) | 0.0035 (5) | 0.0093 (6) |
C12 | 0.0217 (7) | 0.0203 (7) | 0.0186 (7) | 0.0032 (6) | 0.0023 (5) | 0.0038 (6) |
C13 | 0.0199 (7) | 0.0151 (6) | 0.0214 (7) | 0.0051 (5) | 0.0056 (5) | 0.0029 (5) |
S—O1 | 1.4242 (11) | C4—C5 | 1.389 (2) |
S—O2 | 1.4262 (11) | C4—H4 | 0.95 (2) |
S—O3 | 1.6174 (10) | C5—C6 | 1.3932 (19) |
S—C5 | 1.7458 (14) | C6—C7 | 1.385 (2) |
Cl1—C9 | 1.7239 (14) | C6—H6 | 0.965 (18) |
Cl2—C11 | 1.7350 (15) | C7—H7 | 0.93 (2) |
O3—C8 | 1.4021 (16) | C8—C13 | 1.382 (2) |
C1—C2 | 1.504 (2) | C8—C9 | 1.3922 (19) |
C1—H1A | 0.93 (3) | C9—C10 | 1.385 (2) |
C1—H1B | 0.94 (3) | C10—C11 | 1.385 (2) |
C1—H1C | 0.91 (3) | C10—H10 | 0.95 (2) |
C2—C7 | 1.392 (2) | C11—C12 | 1.388 (2) |
C2—C3 | 1.396 (2) | C12—C13 | 1.387 (2) |
C3—C4 | 1.388 (2) | C12—H12 | 0.95 (2) |
C3—H3 | 0.95 (2) | C13—H13 | 0.959 (19) |
O1—S—O2 | 120.41 (7) | C7—C6—C5 | 118.66 (13) |
O1—S—O3 | 102.48 (6) | C7—C6—H6 | 120.8 (11) |
O2—S—O3 | 108.04 (6) | C5—C6—H6 | 120.5 (11) |
O1—S—C5 | 111.35 (7) | C6—C7—C2 | 121.18 (13) |
O2—S—C5 | 109.13 (7) | C6—C7—H7 | 119.6 (14) |
O3—S—C5 | 103.91 (6) | C2—C7—H7 | 119.2 (14) |
C8—O3—S | 117.63 (8) | C13—C8—C9 | 120.71 (13) |
C2—C1—H1A | 111.5 (18) | C13—C8—O3 | 120.44 (12) |
C2—C1—H1B | 112.2 (15) | C9—C8—O3 | 118.80 (12) |
H1A—C1—H1B | 110 (2) | C10—C9—C8 | 120.13 (13) |
C2—C1—H1C | 113.6 (18) | C10—C9—Cl1 | 119.45 (11) |
H1A—C1—H1C | 106 (2) | C8—C9—Cl1 | 120.41 (11) |
H1B—C1—H1C | 103 (2) | C9—C10—C11 | 118.45 (13) |
C7—C2—C3 | 118.77 (13) | C9—C10—H10 | 120.9 (12) |
C7—C2—C1 | 120.25 (14) | C11—C10—H10 | 120.6 (12) |
C3—C2—C1 | 120.97 (14) | C10—C11—C12 | 122.01 (13) |
C4—C3—C2 | 121.27 (14) | C10—C11—Cl2 | 118.77 (11) |
C4—C3—H3 | 117.4 (13) | C12—C11—Cl2 | 119.22 (12) |
C2—C3—H3 | 121.3 (13) | C13—C12—C11 | 118.94 (14) |
C3—C4—C5 | 118.46 (13) | C13—C12—H12 | 119.9 (12) |
C3—C4—H4 | 119.4 (13) | C11—C12—H12 | 121.1 (12) |
C5—C4—H4 | 122.2 (13) | C8—C13—C12 | 119.73 (13) |
C4—C5—C6 | 121.66 (13) | C8—C13—H13 | 118.9 (11) |
C4—C5—S | 119.87 (11) | C12—C13—H13 | 121.3 (11) |
C6—C5—S | 118.45 (11) | ||
O1—S—O3—C8 | −177.68 (10) | C3—C2—C7—C6 | 0.0 (2) |
O2—S—O3—C8 | 54.19 (11) | C1—C2—C7—C6 | −179.66 (14) |
C5—S—O3—C8 | −61.64 (11) | S—O3—C8—C13 | −74.50 (15) |
C7—C2—C3—C4 | −0.3 (2) | S—O3—C8—C9 | 108.25 (12) |
C1—C2—C3—C4 | 179.30 (14) | C13—C8—C9—C10 | 1.9 (2) |
C2—C3—C4—C5 | 0.2 (2) | O3—C8—C9—C10 | 179.14 (12) |
C3—C4—C5—C6 | 0.4 (2) | C13—C8—C9—Cl1 | −176.87 (11) |
C3—C4—C5—S | 178.64 (11) | O3—C8—C9—Cl1 | 0.37 (18) |
O1—S—C5—C4 | 18.90 (14) | C8—C9—C10—C11 | −0.4 (2) |
O2—S—C5—C4 | 154.21 (11) | Cl1—C9—C10—C11 | 178.35 (10) |
O3—S—C5—C4 | −90.73 (12) | C9—C10—C11—C12 | −1.2 (2) |
O1—S—C5—C6 | −162.80 (11) | C9—C10—C11—Cl2 | 179.16 (10) |
O2—S—C5—C6 | −27.49 (13) | C10—C11—C12—C13 | 1.4 (2) |
O3—S—C5—C6 | 87.57 (12) | Cl2—C11—C12—C13 | −178.96 (11) |
C4—C5—C6—C7 | −0.7 (2) | C9—C8—C13—C12 | −1.7 (2) |
S—C5—C6—C7 | −179.01 (11) | O3—C8—C13—C12 | −178.89 (12) |
C5—C6—C7—C2 | 0.6 (2) | C11—C12—C13—C8 | 0.0 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C13—H13···O3i | 0.959 (19) | 2.871 (19) | 3.7361 (18) | 150.5 (14) |
C10—H10···O2ii | 0.95 (2) | 2.47 (2) | 3.3876 (18) | 162.0 (16) |
C7—H7···O3iii | 0.93 (2) | 2.62 (2) | 3.5211 (18) | 163.8 (18) |
C7—H7···O1iii | 0.93 (2) | 3.04 (2) | 3.5505 (19) | 116.3 (16) |
C7—H7···Cl2iv | 0.93 (2) | 2.97 (2) | 3.4404 (15) | 112.9 (16) |
C4—H4···O1v | 0.95 (2) | 2.52 (2) | 3.3907 (18) | 153.6 (17) |
C1—H1B···O1vi | 0.94 (3) | 2.81 (3) | 3.644 (2) | 147.7 (19) |
C1—H1B···O1iii | 0.94 (3) | 2.97 (3) | 3.668 (2) | 131.7 (18) |
C4—H4···O1 | 0.95 (2) | 2.66 (2) | 2.9874 (19) | 100.7 (14) |
C6—H6···O2 | 0.965 (18) | 2.605 (18) | 2.9436 (18) | 100.9 (12) |
C13—H13···O2 | 0.959 (19) | 2.583 (19) | 3.0093 (18) | 107.2 (13) |
C6—H6···Cg2 | 0.97 (2) | 3.388 | 3.778 | 106.6 |
Symmetry codes: (i) −x+1, −y, −z; (ii) x, y+1, z; (iii) x−1, y, z; (iv) −x, −y+1, −z; (v) −x+1, −y, −z+1; (vi) −x, −y, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C13H10Cl2O3S |
Mr | 317.17 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 100 |
a, b, c (Å) | 7.7314 (11), 8.3724 (11), 10.7055 (15) |
α, β, γ (°) | 99.079 (2), 96.119 (2), 103.134 (2) |
V (Å3) | 659.04 (16) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.65 |
Crystal size (mm) | 0.55 × 0.50 × 0.40 |
Data collection | |
Diffractometer | CCD area detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.716, 0.781 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8295, 3074, 2954 |
Rint | 0.015 |
(sin θ/λ)max (Å−1) | 0.669 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.028, 0.077, 1.08 |
No. of reflections | 3074 |
No. of parameters | 212 |
H-atom treatment | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 0.39, −0.32 |
Computer programs: SMART (Bruker, 1998), SMART, SAINT (Bruker, 1998), SHELXTL (Sheldrick, 1998), SHELXTL.
S—O1 | 1.4242 (11) | Cl1—C9 | 1.7239 (14) |
S—O2 | 1.4262 (11) | Cl2—C11 | 1.7350 (15) |
S—O3 | 1.6174 (10) | O3—C8 | 1.4021 (16) |
S—C5 | 1.7458 (14) | C1—C2 | 1.504 (2) |
O1—S—O2 | 120.41 (7) | O2—S—C5 | 109.13 (7) |
O1—S—O3 | 102.48 (6) | O3—S—C5 | 103.91 (6) |
O2—S—O3 | 108.04 (6) | C8—O3—S | 117.63 (8) |
O1—S—C5 | 111.35 (7) | ||
C5—S—O3—C8 | −61.64 (11) |
D—H···A | D—H | H···A | D···A | D—H···A |
C13—H13···O3i | 0.959 (19) | 2.871 (19) | 3.7361 (18) | 150.5 (14) |
C10—H10···O2ii | 0.95 (2) | 2.47 (2) | 3.3876 (18) | 162.0 (16) |
C7—H7···O3iii | 0.93 (2) | 2.62 (2) | 3.5211 (18) | 163.8 (18) |
C7—H7···O1iii | 0.93 (2) | 3.04 (2) | 3.5505 (19) | 116.3 (16) |
C7—H7···Cl2iv | 0.93 (2) | 2.97 (2) | 3.4404 (15) | 112.9 (16) |
C4—H4···O1v | 0.95 (2) | 2.52 (2) | 3.3907 (18) | 153.6 (17) |
C1—H1B···O1vi | 0.94 (3) | 2.81 (3) | 3.644 (2) | 147.7 (19) |
C1—H1B···O1iii | 0.94 (3) | 2.97 (3) | 3.668 (2) | 131.7 (18) |
C4—H4···O1 | 0.95 (2) | 2.66 (2) | 2.9874 (19) | 100.7 (14) |
C6—H6···O2 | 0.965 (18) | 2.605 (18) | 2.9436 (18) | 100.9 (12) |
C13—H13···O2 | 0.959 (19) | 2.583 (19) | 3.0093 (18) | 107.2 (13) |
C6—H6···Cg2 | 0.97 (2) | 3.388 | 3.778 | 106.6 |
Symmetry codes: (i) −x+1, −y, −z; (ii) x, y+1, z; (iii) x−1, y, z; (iv) −x, −y+1, −z; (v) −x+1, −y, −z+1; (vi) −x, −y, −z+1. |
p-Toluene sulfonates are used in monitoring the merging of lipids (Yachi et al., 1989), studying membrane fusion during acrosome reaction (Spungin et al., 1992), development of immunoaffinity chromatography for the purification of human coagulation factor (Tharakan et al., 1992), chemical studies on viruses (Alford et al., 1991), development of technology for linking photosensitizer to model monoclonal antibody (Jiang et al., 1990) and chemical modification of sigma sub units of the E-coli RNA polymerase (Narayanan & Krakow, 1983). An X-ray study of the title compound, (I), was undertaken in order to determine its crystal and molecular structure owing to the biological importance of its analogues.
The dihedral angle between the mean planes of 4-tolyl and 2,4-dichlorophenyl rings is 43.92 (4)°. This shows their non-coplanar orientation similar to that found in 2-chlorophenyl 4-toluenesulfonate (Vembu, Nallu, Garrison & Youngs, 2003b), 8-tosyloxyquinoline (Vembu, Nallu, Garrison & Youngs, 2003c) and in contrast to the near coplanar orientation observed in 2,4-dinitrophenyl 4-toluenesulfonate (Vembu, Nallu, Garrison & Youngs, 2003a) and 4-methoxyphenyl 4-toluenesulfonate (Vembu, Nallu, Garrison, Hindi & Youngs, 2003).
The crystal structure of (I) is stabilized by weak C—H···O interactions. The range for the H···O distances (Table 2) agrees with that found for weak C—H···O bonds (Desiraju & Steiner, 1999). The C4—H4···O1 interaction generates a ring of graph set S(5) (Etter, 1990; Bernstein et al., 1995). Another S(5) motif is formed by the C6—H6.·O2 interaction. The C13—H13···O2 interaction generates a S(6) motif. The C6—H6···O2 and C13—H13···O2 interactions constitute a pair of bifurcated acceptor bonds. The C7—H7···O3iii and C7—H7···O1iii (Fig. 2) interactions constitute a pair of bifurcated donor bonds, generating a ring of graph set R21(4). The H7···O3iii and H7···O1iii distances differ by 0.42 (2) Å. The resulting configuration is termed as an unsymmetrical three-centered H-bonded chelated (Desiraju, 1989) which is different from the symmetrical three centered hygrogen-bonded chelate observed in similar structures (Vembu, Nallu, Garrison & Youngs, 2003b,c; Vembu, Nallu, Garrison, Hindi & Youngs, 2003). The C1—H1B···O1iii and C7—H7···O1iii (Fig. 2) interactions constitute a pair of bifurcated acceptor bonds, generating a ring of graph set R12(6). The C7—H7···O3iii and C1—H1B···O1iii (Fig. 2) interactions generate a R22(8) motif which consists of the R21(4) chelate and R12(6) ring motifs. There are several other C—H···O interactions (Fig. 2–4, Table 2) and a C—H···Cl interaction (Fig. 3) which contribute to the supramolecular aggregation. The supramolecular aggregation is completed by the presence of an intramolecular C—H···π interaction (Table 2). The geometry of the C—H···π interaction was obtained from PLATON (Spek, 1998); Cg2 is the centroid of the 2,4-dichlorophenyl ring. In the crystal lattice, the molecules are stacked in layers (Fig. 5) held together by π···π interactions, with a distance of 4.059 Å and 3.672 Å between the centroids of adjacent 4-tolyl rings (Symmetry code: −x, −y, 1 − z) and 2,4-dichlorophenyl rings (Symmetry code: 1 − x, 1 − y, −z), respectively.