Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807054815/at2462sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807054815/at2462Isup2.hkl |
CCDC reference: 672632
The title compound was synthesized by reacting 1-[2-(ethylsulfonyl)phenyldiazenyl]-4-methoxynaphthalene with disodiumtetrachloropalladate in aqueous ethanol medium at room temperature. The product was purified by chromatography. Crystals suitable for X-ray crystallography was obtained by slow diffusion of dichloromethane solution into hexane.
The O-bound H atom was located in a difference Fourier map and its isotropic displacement parameter were freely refined after fixing the coordinates. C-bound H atoms were included at calculated positions as riding atoms with C–H distances of 0.93 Å for aromatic, 0.96 Å for CH3 and 0.97 Å for CH2 H atoms, with Uiso (H) =1.2Ueq (C) (1.5Ueq for methyl groups).
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL (Bruker, 1997).
[Pd(C9H17N2O3S)Cl]·1.5H2O | F(000) = 2104 |
Mr = 522.31 | Dx = 1.729 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 3904 reflections |
a = 21.1870 (18) Å | θ = 1.7–25.9° |
b = 17.1097 (14) Å | µ = 1.19 mm−1 |
c = 13.4827 (11) Å | T = 295 K |
β = 124.824 (1)° | Needle, pink |
V = 4012.2 (6) Å3 | 0.38 × 0.26 × 0.19 mm |
Z = 8 |
Bruker SMART APEX CCD area detector diffractometer | 3904 independent reflections |
Radiation source: fine-focus sealed tube | 3503 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.020 |
phi and ω scans | θmax = 25.9°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −26→26 |
Tmin = 0.694, Tmax = 0.799 | k = −20→20 |
12258 measured reflections | l = −16→16 |
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: inferred from neighbouring sites |
wR(F2) = 0.083 | H-atom parameters constrained |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0445P)2 + 5.4842P] where P = (Fo2 + 2Fc2)/3 |
3904 reflections | (Δ/σ)max = 0.001 |
262 parameters | Δρmax = 1.07 e Å−3 |
0 restraints | Δρmin = −0.68 e Å−3 |
[Pd(C9H17N2O3S)Cl]·1.5H2O | V = 4012.2 (6) Å3 |
Mr = 522.31 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 21.1870 (18) Å | µ = 1.19 mm−1 |
b = 17.1097 (14) Å | T = 295 K |
c = 13.4827 (11) Å | 0.38 × 0.26 × 0.19 mm |
β = 124.824 (1)° |
Bruker SMART APEX CCD area detector diffractometer | 3904 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 3503 reflections with I > 2σ(I) |
Tmin = 0.694, Tmax = 0.799 | Rint = 0.020 |
12258 measured reflections |
R[F2 > 2σ(F2)] = 0.031 | 0 restraints |
wR(F2) = 0.083 | H-atom parameters constrained |
S = 1.08 | Δρmax = 1.07 e Å−3 |
3904 reflections | Δρmin = −0.68 e Å−3 |
262 parameters |
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 | ||
Pd1 | 0.167430 (12) | 0.985070 (13) | 0.74687 (2) | 0.03443 (9) | |
C2 | 0.09189 (15) | 0.90245 (17) | 0.6922 (2) | 0.0331 (6) | |
S1 | 0.22366 (4) | 1.14847 (5) | 0.85771 (7) | 0.04165 (19) | |
Cl1 | 0.27025 (5) | 0.90451 (5) | 0.81104 (9) | 0.0582 (2) | |
N1 | 0.00874 (14) | 1.01220 (14) | 0.6375 (2) | 0.0354 (5) | |
O2 | 0.24220 (12) | 1.08601 (13) | 0.8039 (2) | 0.0455 (5) | |
O3 | 0.27501 (13) | 1.21410 (14) | 0.9014 (2) | 0.0571 (6) | |
C3 | 0.10189 (16) | 0.82172 (18) | 0.6998 (3) | 0.0379 (6) | |
H3 | 0.1507 | 0.8006 | 0.7355 | 0.046* | |
C1 | 0.01766 (15) | 0.93370 (17) | 0.6381 (2) | 0.0330 (6) | |
N2 | 0.07265 (13) | 1.04999 (14) | 0.6875 (2) | 0.0347 (5) | |
C9 | −0.03752 (16) | 0.80271 (17) | 0.5939 (2) | 0.0354 (6) | |
C10 | −0.04846 (16) | 0.88408 (18) | 0.5863 (2) | 0.0345 (6) | |
O1 | 0.04360 (12) | 0.69462 (13) | 0.6603 (2) | 0.0477 (5) | |
C11 | 0.06450 (17) | 1.13260 (17) | 0.6846 (3) | 0.0362 (6) | |
C4 | 0.03909 (16) | 0.77313 (17) | 0.6542 (3) | 0.0370 (6) | |
C8 | −0.12377 (16) | 0.91331 (19) | 0.5259 (3) | 0.0422 (7) | |
H8 | −0.1318 | 0.9670 | 0.5206 | 0.051* | |
C18 | 0.22294 (19) | 1.1079 (2) | 0.9776 (3) | 0.0491 (8) | |
H18A | 0.2187 | 1.1495 | 1.0224 | 0.059* | |
H18B | 0.1785 | 1.0740 | 0.9450 | 0.059* | |
C5 | −0.10186 (17) | 0.7528 (2) | 0.5393 (3) | 0.0429 (7) | |
H5 | −0.0950 | 0.6989 | 0.5432 | 0.051* | |
C12 | 0.12879 (17) | 1.18202 (18) | 0.7525 (3) | 0.0400 (7) | |
C16 | −0.00722 (18) | 1.16709 (19) | 0.6124 (3) | 0.0419 (7) | |
H16 | −0.0506 | 1.1357 | 0.5675 | 0.050* | |
C6 | −0.17412 (17) | 0.7830 (2) | 0.4809 (3) | 0.0492 (8) | |
H6 | −0.2164 | 0.7497 | 0.4445 | 0.059* | |
C7 | −0.18495 (18) | 0.8641 (2) | 0.4754 (3) | 0.0506 (8) | |
H7 | −0.2344 | 0.8844 | 0.4369 | 0.061* | |
C17 | 0.1169 (2) | 0.6590 (2) | 0.7179 (4) | 0.0663 (11) | |
H17A | 0.1409 | 0.6751 | 0.6786 | 0.099* | |
H17B | 0.1112 | 0.6032 | 0.7129 | 0.099* | |
H17C | 0.1484 | 0.6745 | 0.8012 | 0.099* | |
C13 | 0.1196 (2) | 1.26272 (19) | 0.7420 (3) | 0.0505 (8) | |
H13 | 0.1624 | 1.2950 | 0.7850 | 0.061* | |
C15 | −0.0153 (2) | 1.2474 (2) | 0.6061 (3) | 0.0494 (8) | |
H15 | −0.0642 | 1.2694 | 0.5589 | 0.059* | |
C14 | 0.0481 (2) | 1.2949 (2) | 0.6691 (3) | 0.0549 (9) | |
H14 | 0.0424 | 1.3490 | 0.6621 | 0.066* | |
C19 | 0.2955 (2) | 1.0614 (3) | 1.0621 (4) | 0.0700 (11) | |
H19A | 0.2948 | 1.0145 | 1.0223 | 0.105* | |
H19B | 0.2981 | 1.0479 | 1.1335 | 0.105* | |
H19C | 0.3395 | 1.0922 | 1.0840 | 0.105* | |
O4 | 0.4461 (4) | 1.0023 (4) | 1.0164 (7) | 0.180 (3) | |
O5 | 0.0000 | 0.5318 (7) | 0.7500 | 0.221 (5) | |
H5A | −0.0150 | 0.5680 | 0.6840 | 1.0 (3)* | |
H4B | 0.4840 | 0.9970 | 1.0000 | 0.150* | |
H4A | 0.4280 | 0.9480 | 1.0100 | 0.37 (9)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Pd1 | 0.02794 (13) | 0.03781 (15) | 0.03805 (15) | −0.00271 (8) | 0.01914 (11) | −0.00357 (9) |
C2 | 0.0302 (13) | 0.0405 (15) | 0.0278 (13) | −0.0038 (11) | 0.0162 (11) | −0.0027 (11) |
S1 | 0.0362 (4) | 0.0378 (4) | 0.0512 (4) | −0.0080 (3) | 0.0251 (4) | −0.0050 (3) |
Cl1 | 0.0369 (4) | 0.0491 (5) | 0.0855 (6) | 0.0040 (3) | 0.0331 (4) | −0.0021 (4) |
N1 | 0.0319 (12) | 0.0433 (14) | 0.0316 (12) | −0.0012 (10) | 0.0185 (11) | −0.0021 (10) |
O2 | 0.0379 (11) | 0.0475 (13) | 0.0556 (13) | −0.0094 (9) | 0.0295 (11) | −0.0069 (10) |
O3 | 0.0456 (13) | 0.0448 (13) | 0.0768 (17) | −0.0139 (10) | 0.0326 (13) | −0.0100 (12) |
C3 | 0.0291 (14) | 0.0435 (16) | 0.0364 (15) | −0.0001 (12) | 0.0158 (12) | −0.0026 (12) |
C1 | 0.0307 (13) | 0.0403 (16) | 0.0291 (14) | −0.0028 (12) | 0.0177 (12) | −0.0037 (11) |
N2 | 0.0313 (12) | 0.0391 (13) | 0.0345 (12) | −0.0007 (10) | 0.0193 (10) | −0.0010 (10) |
C9 | 0.0327 (14) | 0.0425 (16) | 0.0321 (14) | −0.0028 (12) | 0.0191 (12) | −0.0032 (12) |
C10 | 0.0304 (13) | 0.0448 (16) | 0.0275 (13) | −0.0021 (12) | 0.0161 (11) | −0.0051 (12) |
O1 | 0.0374 (11) | 0.0386 (12) | 0.0606 (14) | 0.0006 (9) | 0.0242 (11) | −0.0002 (10) |
C11 | 0.0405 (15) | 0.0392 (16) | 0.0358 (15) | 0.0003 (12) | 0.0259 (13) | −0.0016 (12) |
C4 | 0.0349 (14) | 0.0399 (16) | 0.0341 (15) | −0.0012 (12) | 0.0185 (13) | −0.0025 (12) |
C8 | 0.0329 (15) | 0.0470 (18) | 0.0415 (16) | 0.0034 (13) | 0.0181 (13) | −0.0056 (13) |
C18 | 0.0490 (18) | 0.0493 (19) | 0.0474 (19) | −0.0071 (15) | 0.0266 (16) | −0.0062 (15) |
C5 | 0.0373 (15) | 0.0453 (18) | 0.0444 (17) | −0.0080 (13) | 0.0223 (14) | −0.0081 (14) |
C12 | 0.0395 (15) | 0.0385 (16) | 0.0462 (17) | −0.0020 (13) | 0.0269 (14) | 0.0002 (13) |
C16 | 0.0420 (16) | 0.0467 (18) | 0.0387 (16) | 0.0039 (13) | 0.0240 (14) | 0.0023 (13) |
C6 | 0.0330 (16) | 0.058 (2) | 0.0501 (19) | −0.0119 (14) | 0.0200 (15) | −0.0139 (16) |
C7 | 0.0279 (15) | 0.063 (2) | 0.0506 (19) | −0.0002 (14) | 0.0161 (14) | −0.0092 (16) |
C17 | 0.0419 (19) | 0.045 (2) | 0.097 (3) | 0.0077 (16) | 0.031 (2) | 0.006 (2) |
C13 | 0.0541 (19) | 0.0381 (17) | 0.061 (2) | −0.0064 (15) | 0.0336 (18) | −0.0025 (15) |
C15 | 0.0516 (19) | 0.052 (2) | 0.0458 (18) | 0.0125 (16) | 0.0286 (16) | 0.0072 (15) |
C14 | 0.069 (2) | 0.0399 (18) | 0.061 (2) | 0.0086 (17) | 0.040 (2) | 0.0069 (16) |
C19 | 0.076 (3) | 0.066 (3) | 0.054 (2) | 0.008 (2) | 0.029 (2) | 0.0016 (19) |
O4 | 0.146 (5) | 0.171 (6) | 0.165 (6) | −0.029 (4) | 0.054 (5) | 0.013 (4) |
O5 | 0.143 (7) | 0.224 (10) | 0.341 (15) | 0.000 | 0.166 (10) | 0.000 |
Pd1—C2 | 1.938 (3) | C18—C19 | 1.514 (5) |
Pd1—N2 | 2.018 (2) | C18—H18A | 0.9700 |
Pd1—O2 | 2.166 (2) | C18—H18B | 0.9700 |
Pd1—Cl1 | 2.2895 (8) | C5—C6 | 1.362 (4) |
C2—C3 | 1.392 (4) | C5—H5 | 0.9300 |
C2—C1 | 1.408 (4) | C12—C13 | 1.390 (5) |
S1—O3 | 1.435 (2) | C16—C15 | 1.381 (5) |
S1—O2 | 1.466 (2) | C16—H16 | 0.9300 |
S1—C18 | 1.768 (3) | C6—C7 | 1.402 (5) |
S1—C12 | 1.768 (3) | C6—H6 | 0.9300 |
N1—N2 | 1.290 (3) | C7—H7 | 0.9300 |
N1—C1 | 1.356 (4) | C17—H17A | 0.9600 |
C3—C4 | 1.380 (4) | C17—H17B | 0.9600 |
C3—H3 | 0.9300 | C17—H17C | 0.9600 |
C1—C10 | 1.433 (4) | C13—C14 | 1.365 (5) |
N2—C11 | 1.422 (4) | C13—H13 | 0.9300 |
C9—C10 | 1.405 (4) | C15—C14 | 1.374 (5) |
C9—C5 | 1.408 (4) | C15—H15 | 0.9300 |
C9—C4 | 1.430 (4) | C14—H14 | 0.9300 |
C10—C8 | 1.405 (4) | C19—H19A | 0.9600 |
O1—C4 | 1.346 (4) | C19—H19B | 0.9600 |
O1—C17 | 1.418 (4) | C19—H19C | 0.9600 |
C11—C16 | 1.384 (4) | O4—H4B | 0.9500 |
C11—C12 | 1.409 (4) | O4—H4A | 0.9900 |
C8—C7 | 1.358 (4) | O5—H5A | 0.9800 |
C8—H8 | 0.9300 | ||
C2—Pd1—N2 | 80.32 (11) | C19—C18—H18A | 109.4 |
C2—Pd1—O2 | 173.86 (10) | S1—C18—H18A | 109.4 |
N2—Pd1—O2 | 93.58 (9) | C19—C18—H18B | 109.4 |
C2—Pd1—Cl1 | 96.06 (9) | S1—C18—H18B | 109.4 |
N2—Pd1—Cl1 | 176.38 (7) | H18A—C18—H18B | 108.0 |
O2—Pd1—Cl1 | 90.04 (6) | C6—C5—C9 | 120.3 (3) |
C3—C2—C1 | 119.5 (2) | C6—C5—H5 | 119.8 |
C3—C2—Pd1 | 129.6 (2) | C9—C5—H5 | 119.8 |
C1—C2—Pd1 | 110.8 (2) | C13—C12—C11 | 120.2 (3) |
O3—S1—O2 | 114.78 (14) | C13—C12—S1 | 115.7 (2) |
O3—S1—C18 | 109.40 (16) | C11—C12—S1 | 124.1 (2) |
O2—S1—C18 | 108.13 (15) | C15—C16—C11 | 121.0 (3) |
O3—S1—C12 | 108.86 (15) | C15—C16—H16 | 119.5 |
O2—S1—C12 | 110.03 (14) | C11—C16—H16 | 119.5 |
C18—S1—C12 | 105.20 (15) | C5—C6—C7 | 120.2 (3) |
N2—N1—C1 | 113.1 (2) | C5—C6—H6 | 119.9 |
S1—O2—Pd1 | 114.10 (11) | C7—C6—H6 | 119.9 |
C4—C3—C2 | 119.8 (3) | C8—C7—C6 | 120.4 (3) |
C4—C3—H3 | 120.1 | C8—C7—H7 | 119.8 |
C2—C3—H3 | 120.1 | C6—C7—H7 | 119.8 |
N1—C1—C2 | 119.3 (2) | O1—C17—H17A | 109.5 |
N1—C1—C10 | 119.3 (2) | O1—C17—H17B | 109.5 |
C2—C1—C10 | 121.3 (3) | H17A—C17—H17B | 109.5 |
N1—N2—C11 | 114.2 (2) | O1—C17—H17C | 109.5 |
N1—N2—Pd1 | 116.19 (19) | H17A—C17—H17C | 109.5 |
C11—N2—Pd1 | 129.48 (19) | H17B—C17—H17C | 109.5 |
C10—C9—C5 | 119.5 (3) | C14—C13—C12 | 120.5 (3) |
C10—C9—C4 | 118.6 (3) | C14—C13—H13 | 119.7 |
C5—C9—C4 | 121.9 (3) | C12—C13—H13 | 119.7 |
C9—C10—C8 | 118.7 (3) | C14—C15—C16 | 120.5 (3) |
C9—C10—C1 | 118.5 (2) | C14—C15—H15 | 119.7 |
C8—C10—C1 | 122.8 (3) | C16—C15—H15 | 119.7 |
C4—O1—C17 | 118.7 (2) | C13—C14—C15 | 119.8 (3) |
C16—C11—C12 | 117.8 (3) | C13—C14—H14 | 120.1 |
C16—C11—N2 | 120.7 (3) | C15—C14—H14 | 120.1 |
C12—C11—N2 | 121.4 (3) | C18—C19—H19A | 109.5 |
O1—C4—C3 | 123.9 (3) | C18—C19—H19B | 109.5 |
O1—C4—C9 | 113.9 (2) | H19A—C19—H19B | 109.5 |
C3—C4—C9 | 122.2 (3) | C18—C19—H19C | 109.5 |
C7—C8—C10 | 120.8 (3) | H19A—C19—H19C | 109.5 |
C7—C8—H8 | 119.6 | H19B—C19—H19C | 109.5 |
C10—C8—H8 | 119.6 | H4B—O4—H4A | 103.0 |
C19—C18—S1 | 111.0 (3) | ||
N2—Pd1—C2—C3 | −176.2 (3) | C17—O1—C4—C3 | 0.7 (5) |
Cl1—Pd1—C2—C3 | 3.6 (3) | C17—O1—C4—C9 | 179.8 (3) |
N2—Pd1—C2—C1 | 3.79 (18) | C2—C3—C4—O1 | −178.2 (3) |
Cl1—Pd1—C2—C1 | −176.32 (18) | C2—C3—C4—C9 | 2.7 (4) |
O3—S1—O2—Pd1 | 177.03 (14) | C10—C9—C4—O1 | 177.8 (2) |
C18—S1—O2—Pd1 | 54.61 (17) | C5—C9—C4—O1 | −4.2 (4) |
C12—S1—O2—Pd1 | −59.78 (17) | C10—C9—C4—C3 | −3.1 (4) |
N2—Pd1—O2—S1 | 38.00 (15) | C5—C9—C4—C3 | 175.0 (3) |
Cl1—Pd1—O2—S1 | −141.84 (13) | C9—C10—C8—C7 | −0.3 (4) |
C1—C2—C3—C4 | 0.1 (4) | C1—C10—C8—C7 | 178.3 (3) |
Pd1—C2—C3—C4 | −179.9 (2) | O3—S1—C18—C19 | −75.3 (3) |
N2—N1—C1—C2 | 1.0 (4) | O2—S1—C18—C19 | 50.3 (3) |
N2—N1—C1—C10 | 179.6 (2) | C12—S1—C18—C19 | 167.9 (3) |
C3—C2—C1—N1 | 176.1 (2) | C10—C9—C5—C6 | −0.9 (4) |
Pd1—C2—C1—N1 | −4.0 (3) | C4—C9—C5—C6 | −178.9 (3) |
C3—C2—C1—C10 | −2.5 (4) | C16—C11—C12—C13 | −2.7 (4) |
Pd1—C2—C1—C10 | 177.5 (2) | N2—C11—C12—C13 | 176.0 (3) |
C1—N1—N2—C11 | 178.1 (2) | C16—C11—C12—S1 | 175.1 (2) |
C1—N1—N2—Pd1 | 2.4 (3) | N2—C11—C12—S1 | −6.2 (4) |
C2—Pd1—N2—N1 | −3.68 (19) | O3—S1—C12—C13 | −7.3 (3) |
O2—Pd1—N2—N1 | 176.99 (19) | O2—S1—C12—C13 | −133.9 (2) |
C2—Pd1—N2—C11 | −178.6 (2) | C18—S1—C12—C13 | 109.8 (3) |
O2—Pd1—N2—C11 | 2.1 (2) | O3—S1—C12—C11 | 174.8 (2) |
C5—C9—C10—C8 | 1.2 (4) | O2—S1—C12—C11 | 48.2 (3) |
C4—C9—C10—C8 | 179.3 (3) | C18—S1—C12—C11 | −68.1 (3) |
C5—C9—C10—C1 | −177.4 (3) | C12—C11—C16—C15 | 0.8 (4) |
C4—C9—C10—C1 | 0.6 (4) | N2—C11—C16—C15 | −177.9 (3) |
N1—C1—C10—C9 | −176.4 (2) | C9—C5—C6—C7 | −0.5 (5) |
C2—C1—C10—C9 | 2.1 (4) | C10—C8—C7—C6 | −1.0 (5) |
N1—C1—C10—C8 | 4.9 (4) | C5—C6—C7—C8 | 1.4 (5) |
C2—C1—C10—C8 | −176.6 (3) | C11—C12—C13—C14 | 2.1 (5) |
N1—N2—C11—C16 | −12.3 (4) | S1—C12—C13—C14 | −175.8 (3) |
Pd1—N2—C11—C16 | 162.7 (2) | C11—C16—C15—C14 | 1.8 (5) |
N1—N2—C11—C12 | 169.0 (3) | C12—C13—C14—C15 | 0.4 (5) |
Pd1—N2—C11—C12 | −16.0 (4) | C16—C15—C14—C13 | −2.4 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···Cl1 | 0.93 | 2.77 | 3.297 (4) | 117 |
C13—H13···O3 | 0.93 | 2.41 | 2.841 (5) | 108 |
C18—H18A···O3i | 0.97 | 2.52 | 3.443 (4) | 158 |
Symmetry code: (i) −x+1/2, −y+5/2, −z+2. |
Experimental details
Crystal data | |
Chemical formula | [Pd(C9H17N2O3S)Cl]·1.5H2O |
Mr | 522.31 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 295 |
a, b, c (Å) | 21.1870 (18), 17.1097 (14), 13.4827 (11) |
β (°) | 124.824 (1) |
V (Å3) | 4012.2 (6) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 1.19 |
Crystal size (mm) | 0.38 × 0.26 × 0.19 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD area detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.694, 0.799 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12258, 3904, 3503 |
Rint | 0.020 |
(sin θ/λ)max (Å−1) | 0.615 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.031, 0.083, 1.08 |
No. of reflections | 3904 |
No. of parameters | 262 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 1.07, −0.68 |
Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997).
Pd1—C2 | 1.938 (3) | Pd1—O2 | 2.166 (2) |
Pd1—N2 | 2.018 (2) | Pd1—Cl1 | 2.2895 (8) |
C2—Pd1—N2 | 80.32 (11) | C2—Pd1—Cl1 | 96.06 (9) |
N2—Pd1—O2 | 93.58 (9) | O2—Pd1—Cl1 | 90.04 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···Cl1 | 0.93 | 2.77 | 3.297 (4) | 117 |
C13—H13···O3 | 0.93 | 2.41 | 2.841 (5) | 108 |
C18—H18A···O3i | 0.97 | 2.52 | 3.443 (4) | 158 |
Symmetry code: (i) −x+1/2, −y+5/2, −z+2. |
Cyclopalladated compounds find numerous applications (Dupont et al., 2005) in organic synthesis, catalysis, photochemistry and metallomesogen chemistry. Although a number of cyclometallated complexes of palladium (Dupont et al., 2005 & Neogi et al., 2006) have been reported in literature, the chemistry of cyclopalladates having sulfonyl ligand framework is not explored much. Against this background, we report here the crystal structure of (I).
The molecular structure of the title compound, (I), is shown in Fig. 1, with the atom numbering scheme. The palladium atom along with donor set of four atoms lie in a plane. Selected bond lengths and bond angles are listed in Table 1. The packing arrangement of (I) is shown in Fig. 2. The N=N bond length is typical of other cyclopalladated azoarenes (Neogi et al., 2006). A hydrophilic environment wrapping the polar portion of the compound is being created by an array of water molecules. Intramolecular C–H···Cl and C–H···O interactions are also present in (I) (Table 2, Fig. 3). The crystal packing is stabilized by a intermolecular C18–H18A···O3i [Symmetry codes: (i) -x + 1/2, -y + 5/2, -z + 2.] interaction (Table 2, Fig. 3) and eight intermolecular π–π interactions (Bagchi et al., 2007); the Cg3-Cg3ii, Cg3-Cg4ii, Cg3—Cg5iii, Cg4—Cg3ii, Cg4—Cg5iii, Cg5—Cg3iii, Cg5—Cg4iii and Cg5—Cg5ii [Symmetry codes: (ii) -x, y, 1/2 - z; (iii) -x, -y, -z.Cg3, Cg4 and Cg5 are the centroids of C1—C10, C5—C9 and C11—C16 rings respectively.] distances are 3.647 (2), 3.6495 (18), 3.8098 (18), 3.6495 (18), 3.740 (2), 3.8098 (18), 3.740 (2) and 3.850 (3) Å (Fig. 4); the corresponding perpendicular distances are 3.396, 3.402, 3.169, 3.464, 3.590, 3.462, 3.434 and 3.480 Å respectively.