Chlorido{1-[2-(ethyl­sulfon­yl)phenyl­diazen­yl]-4-meth­oxy-2-naphthyl-κ³C,N,O}palladium(II) sesquihydrate

In the title compound, [Pd(C₉H₁₇N₂O₃S)Cl]·1.5H₂O, the Pd atom is tetra­coordinated by a naphthyl C, a diazene N, a Cl and a sulfonyl O atom in an approximate square-planar geometry; the asymmetric unit also contains 1.5 molecules of water, one molecule lying on a twofold rotation axis. A hydro­philic environment wrapping the polar portion of the compound is created by an array of water mol­ecules. The crystal packing is stabilized by an inter­molecular C—H...O inter­action and eight inter­molecular π–π inter­actions; the centroid–centroid distances range from 3.647 (2)–3.8098 (18) Å, with perpendicular interplanar distances between 3.169 and 3.590 Å.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.031
• wR factor = 0.083
• Data-to-parameter ratio = 14.9

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT417_ALERT_2_B Short Inter D-H..H-D       H4A    ..  H5A     ..       1.95 Ang.
PLAT420_ALERT_2_B D-H Without Acceptor       O4     -   H4A    ...          ?

Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............       0.50 Ratio
PLAT245_ALERT_2_C U(iso) H4B     Smaller than U(eq) O4      by ...       0.03 AngSq

Alert level G
PLAT794_ALERT_5_G Check Predicted Bond Valency for Pd1         (2)       2.03

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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S1. Comment

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.

Related literature

For related literature, see: Bagchi et al. (2007); Dupont et al. (2005); Neogi et al. (2006); Ersanlı, Albayrak, Odabaşoğlu & Kazak (2005); Ghedini et al. (1991); Lanfredi et al. (1984).

S2. Experimental

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.

S3. Refinement

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 U_iso (H) =1.2U_eq (C) (1.5U_eq for methyl groups).

Computing details

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).

Figures

	Fig. 1. The asymmetric unit of (I), with displacement ellipsoids drawn at the 50% probability level. Solvent molecules are omited for clarity.
	Fig. 2. The molecular arrangement of (I) in the ac plane.
	Fig. 3. A representation of the intramolecular C—H···O, C—H···Cl (dotted lines), intermolecular C—H···O (dashed lines) interactions of (I) [symmetry code: (i) -x + 1/2, -y + 5/2, -z + 2.]. Solvent molecules are omited for clarity.
	Fig. 4. The inter molecular π—π interaction for (I), indicated by the dotted line. [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.]

Chlorido{1-[2-(ethylsulfonyl)phenyldiazenyl]-4-methoxy-2-naphthyl- κ³C,N,O}palladium(II) sesquihydrate

Crystal data

[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) Å^3	0.38 × 0.26 × 0.19 mm
Z = 8

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.083	H-atom parameters constrained
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0445P)^2 + 5.4842P] where P = (Fo^2 + 2Fc^2)/3
3904 reflections	(Δ/σ)max = 0.001
262 parameters	Δρmax = 1.07 e Å^−3
0 restraints	Δρmin = −0.68 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	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)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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

Geometric parameters (Å, º)

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)

Hydrogen-bond geometry (Å, º)

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···O3^i	0.97	2.52	3.443 (4)	158

Symmetry code: (i) −x+1/2, −y+5/2, −z+2.