catena-Poly[[bis­(p-toluene­sulfonato-κO)palladium(II)]bis­(μ-1,3-di-4-pyridylpropane-κ2N:N′)]

Wang, S.; Yang, T.; Li, Z.; Yu, X.

doi:10.1107/S1600536809032760

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 9| September 2009| Page m1116

doi:10.1107/S1600536809032760

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catena-Poly[[bis(p-toluenesulfonato-κO)palladium(II)]bis(μ-1,3-di-4-pyridylpropane-κ²N:N′)]

Suwen Wang,^a Tianyu Yang,^b Zhongfang Li ^a ^* and Xianjin Yu ^a

^aCollege of Chemical Engineering, Shandong University of Technology, Zibo 255049, People's Republic of China, and ^bThe College of Life Sciences, Northwest University, Xi-an 710069, People's Republic of China
^*Correspondence e-mail: zhfli_sdut@yahoo.cn

(Received 25 July 2009; accepted 17 August 2009; online 22 August 2009)

In the title compound, [Pd(C₇H₇O₃S)₂(C₁₃H₁₄N₂)₂]_n, the metal ion, located on a twofold rotation axis, exhibits a slightly distorted octahedral coordination environment, with bond angles that deviate by at most 2.2° from an ideal geometry, completed by two O atoms from two deprotonated p-toluenesulfonic acid ligands and four N atoms from four 1,3-di-4-pyridylpropane ligands. One of the sulfonate O atoms is disordered over two positions [ratio 0.70 (5):0.30 (5)].

Related literature

For the potential applications of metal-organic frameworks, see: Jia et al. (2007 ); Li et al. (1996 ); Seo et al. (2000 ); Hagrman et al. (1999 ); Yaghi et al. (1998 ); Kortz et al. (2003 ); Liu et al. (2007 ); Wang et al. (2007 ). 1,3-Di(4-pyridyl)propane has versatile coordination modes with transition metal centers, see: Xu et al. (2004 ); Zhu et al. (2002 ); Mock & Morsch (2001 ).

Experimental

Crystal data

[Pd(C₇H₇O₃S)₂(C₁₃H₁₄N₂)₂]
M_r = 845.3
Orthorhombic, P n n a
a = 23.818 (2) Å
b = 17.4359 (10) Å
c = 9.3341 (10) Å
V = 3876.3 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.64 mm⁻¹
T = 273 K
0.12 × 0.08 × 0.01 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.927, T_max = 0.994
18799 measured reflections
3374 independent reflections
2761 reflections with I > 2σ(I)
R_int = 0.068

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.091
S = 1.08
3374 reflections
251 parameters
H-atom parameters not refined
Δρ_max = 0.61 e Å⁻³
Δρ_min = −0.67 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809032760/bx2229sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809032760/bx2229Isup2.hkl

checkCIF report

Comment top

Design and construction of metal-organic frameworks (MOFs) have attracted considerable attention in recent years, not only for their intriguing structural motifs but also for their potential applications in the areas of catalysis, separation, gas absorption, molecular recognition, nonlinear optics, and magnetochemistry (Jia et al. (2007); Li et al. (1996); Seo et al. (2000); Hagrman et al. (1999); Yaghi et al. (1998); Kortz et al. (2003); Liu et al. (2007); Wang et al. (2007)). A successful strategy for the design and synthesis of predictable MOFs is the assembly reaction between metal ions and well designed organic ligands. 1,3-di(4-pyridyl)proane is a very good choice for preparing such MOFs because of its versatile coordination modes with transition metal centers (Xu et al. (2004); Zhu et al. (2002); Mock et al. (2001)). We report here the crystal and molecular structure of the title compound, (I).

In the asymmetric unit of complex (I), exhibit one 1,3-di(4-pyridyl)propane ligand, one depronated p-toluenesulfonic acid, and one Pd(II) ion, figure 1.The metal exhibits an octahedral coordination environment with bond angles that do not exceed 2.2° from the ideal geometry completed by two oxygen atoms from two depronated p-Toluenesulfonic acid and four nitrogen atoms from four 3-(2-pyridyl)pyrazole ligand.The bond distances of Pd—O and Pd—N are in the range of 2.326 (2)–2.339 (2) and 2.338 (2) Å, respectively.The O1 atom is disordered over two positions [0.70 (5)/0.30 (5)].

Related literature top

For the potential applications of metal-organic frameworks, see: Jia et al. (2007); Li et al. (1996); Seo et al. (2000); Hagrman et al. (1999); Yaghi et al. (1998); Kortz et al. (2003); Liu et al. (2007); Wang et al. (2007). 1,3-Di(4-pyridyl)proane has versatile coordination modes with transition metal centers, see: Xu et al. (2004); Zhu et al. (2002); Mock et al. (2001).

Experimental top

A mixture of Pd(II) chloride (1 mmoL), p-Toluenesulfonic acid (1 mmoL), and 1,3-di(4-pyridyl)proane (1 mmoL) in 10 ml distilled water sealed in a 25 ml Teflon-lined stainless steel autoclave was kept at 433 K for three days. Colorless crystals suitable for the X-ray experiment were obtained. Anal. Calc. for C₄₀H₄₂N₄O₆PdS₂: C 56.78, H 4.97, N 6.62%; Found: C 56.35, H 4.78, N 6.52%.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); 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 (Sheldrick, 2008).

Figures top

Fig. 1. A view of (I) with the unique atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. Minor component of disordered O1 atom as well as H atoms have been omitted. Unlabeled atoms are related to labeled atoms by the symmetry code (x, 1/2 - y, 1/2 - z)

catena-Poly[[bis(p-toluenesulfonato- κO)palladium(II)]bis(µ-1,3-di-4-pyridylpropane- κ²N:N')] top

Crystal data top

[Pd(C₇H₇O₃S)₂(C₁₃H₁₄N₂)₂]	F(000) = 1744
M_r = 845.3	D_x = 1.448 Mg m⁻³
Orthorhombic, Pnna	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2a 2bc	Cell parameters from 7795 reflections
a = 23.818 (2) Å	θ = 2.4–28.2°
b = 17.4359 (10) Å	µ = 0.64 mm⁻¹
c = 9.3341 (10) Å	T = 273 K
V = 3876.3 (6) Å³	Block, colorless
Z = 4	0.12 × 0.08 × 0.01 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	3374 independent reflections
Radiation source: fine-focus sealed tube	2761 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.068
ϕ and ω scans	θ_max = 25°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −28→26
T_min = 0.927, T_max = 0.994	k = −20→20
18799 measured reflections	l = −11→9

Refinement top

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.091	H-atom parameters not refined
S = 1.08	w = 1/[σ²(F_o²) + (0.0492P)² + 0.7971P] where P = (F_o² + 2F_c²)/3
3374 reflections	(Δ/σ)_max = 0.047
251 parameters	Δρ_max = 0.61 e Å⁻³
0 restraints	Δρ_min = −0.67 e Å⁻³

Crystal data top

[Pd(C₇H₇O₃S)₂(C₁₃H₁₄N₂)₂]	V = 3876.3 (6) Å³
M_r = 845.3	Z = 4
Orthorhombic, Pnna	Mo Kα radiation
a = 23.818 (2) Å	µ = 0.64 mm⁻¹
b = 17.4359 (10) Å	T = 273 K
c = 9.3341 (10) Å	0.12 × 0.08 × 0.01 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	3374 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2761 reflections with I > 2σ(I)
T_min = 0.927, T_max = 0.994	R_int = 0.068
18799 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.091	H-atom parameters not refined
S = 1.08	Δρ_max = 0.61 e Å⁻³
3374 reflections	Δρ_min = −0.67 e Å⁻³
251 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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 (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Pd1	0.405803 (9)	0.25	0.25	0.02547 (12)
S1	0.38959 (4)	0.12445 (5)	0.56888 (8)	0.0569 (2)
O1A	0.453 (3)	0.1210 (9)	0.624 (7)	0.110 (16)	0.30 (5)
O1B	0.4230 (9)	0.1297 (6)	0.6913 (16)	0.095 (4)	0.70 (5)
O2	0.40587 (9)	0.15978 (13)	0.4355 (3)	0.0623 (6)
O3	0.33358 (13)	0.15336 (15)	0.6086 (3)	0.1029 (11)
N1	0.47636 (8)	0.18031 (12)	0.1367 (2)	0.0352 (5)
N2	0.33394 (8)	0.17892 (12)	0.1424 (3)	0.0383 (5)
C1	0.3609 (3)	−0.2217 (3)	0.4820 (7)	0.144 (2)
H1A	0.3825	−0.2462	0.5559	0.216*
H1B	0.3744	−0.2378	0.3899	0.216*
H1C	0.3221	−0.2357	0.4918	0.216*
C2	0.3669 (2)	−0.1344 (2)	0.4956 (4)	0.0741 (11)
C3	0.32559 (17)	−0.0900 (2)	0.5550 (4)	0.0739 (11)
H3	0.2924	−0.1132	0.5847	0.089*
C4	0.33176 (13)	−0.01173 (19)	0.5722 (3)	0.0561 (8)
H4	0.3027	0.0166	0.6125	0.067*
C5	0.37985 (12)	0.02464 (16)	0.5309 (3)	0.0405 (6)
C6	0.42192 (14)	−0.0190 (2)	0.4681 (3)	0.0520 (8)
H6	0.4549	0.0043	0.4371	0.062*
C7	0.41461 (17)	−0.0978 (2)	0.4516 (4)	0.0663 (10)
H7	0.4431	−0.1264	0.4093	0.08*
C8	0.48162 (10)	0.16862 (16)	−0.0055 (3)	0.0386 (6)
H8	0.4599	0.1982	−0.067	0.046*
C9	0.51733 (10)	0.11541 (16)	−0.0644 (3)	0.0389 (6)
H9	0.519	0.1092	−0.1632	0.047*
C10	0.50992 (12)	0.13828 (18)	0.2226 (3)	0.0408 (7)
H10	0.5079	0.1461	0.321	0.049*
C11	0.54674 (10)	0.08471 (16)	0.1715 (3)	0.0410 (7)
H11	0.5691	0.0572	0.2351	0.049*
C12	0.55099 (10)	0.07100 (14)	0.0245 (3)	0.0339 (6)
C13	0.58962 (10)	0.01068 (17)	−0.0364 (4)	0.0442 (7)
H13A	0.5701	−0.0172	−0.1113	0.053*
H13B	0.5993	−0.0256	0.0385	0.053*
C14	0.64305 (10)	0.04495 (15)	−0.0976 (3)	0.0398 (6)
H14A	0.662	0.0064	−0.1547	0.048*
H14B	0.6332	0.0871	−0.1605	0.048*
C15	0.32321 (11)	0.17269 (16)	0.0008 (3)	0.0402 (6)
H15	0.3494	0.1923	−0.0634	0.048*
C16	0.29563 (12)	0.15034 (19)	0.2325 (3)	0.0423 (7)
H16	0.3019	0.1544	0.3306	0.051*
C17	0.24731 (11)	0.11523 (15)	0.1860 (3)	0.0413 (6)
H17	0.2221	0.0952	0.2523	0.05*
C18	0.27591 (11)	0.13906 (16)	−0.0530 (3)	0.0419 (7)
H18	0.2705	0.136	−0.1516	0.05*
C19	0.23581 (10)	0.10944 (14)	0.0402 (3)	0.0341 (6)
C20	0.18311 (10)	0.07391 (16)	−0.0165 (3)	0.0380 (6)
H20A	0.1932	0.0314	−0.0783	0.046*
H20B	0.1637	0.1115	−0.0748	0.046*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pd1	0.01639 (17)	0.02857 (17)	0.03145 (18)	0	0	−0.00186 (10)
S1	0.0873 (6)	0.0455 (4)	0.0379 (4)	−0.0102 (4)	−0.0087 (4)	0.0075 (3)
O1A	0.17 (3)	0.066 (7)	0.09 (3)	−0.003 (9)	−0.09 (2)	0.001 (8)
O1B	0.157 (9)	0.075 (3)	0.051 (5)	−0.031 (4)	−0.053 (6)	−0.004 (4)
O2	0.0648 (14)	0.0570 (14)	0.0652 (15)	−0.0050 (10)	0.0055 (11)	0.0284 (12)
O3	0.131 (3)	0.0669 (17)	0.111 (2)	0.0160 (17)	0.070 (2)	−0.0008 (16)
N1	0.0283 (11)	0.0425 (12)	0.0347 (12)	0.0029 (9)	−0.0016 (9)	−0.0028 (10)
N2	0.0273 (11)	0.0437 (13)	0.0438 (14)	−0.0045 (9)	0.0016 (10)	−0.0048 (11)
C1	0.238 (7)	0.055 (3)	0.139 (5)	−0.016 (4)	−0.024 (5)	−0.015 (3)
C2	0.112 (3)	0.050 (2)	0.060 (2)	−0.011 (2)	−0.016 (2)	0.0012 (18)
C3	0.074 (2)	0.067 (2)	0.081 (3)	−0.027 (2)	−0.007 (2)	0.012 (2)
C4	0.0464 (17)	0.061 (2)	0.061 (2)	−0.0019 (15)	0.0018 (15)	0.0076 (17)
C5	0.0437 (16)	0.0474 (16)	0.0304 (14)	0.0013 (13)	−0.0044 (12)	0.0069 (12)
C6	0.0503 (17)	0.070 (2)	0.0361 (16)	0.0020 (16)	−0.0016 (14)	0.0063 (15)
C7	0.092 (3)	0.065 (2)	0.0421 (19)	0.029 (2)	−0.0071 (19)	−0.0055 (17)
C8	0.0314 (14)	0.0502 (16)	0.0342 (14)	0.0048 (12)	0.0004 (12)	0.0043 (12)
C9	0.0332 (14)	0.0546 (16)	0.0291 (14)	0.0025 (12)	0.0021 (11)	−0.0025 (12)
C10	0.0342 (15)	0.0593 (18)	0.0290 (14)	0.0092 (14)	−0.0006 (11)	−0.0013 (12)
C11	0.0300 (14)	0.0534 (17)	0.0397 (17)	0.0118 (12)	−0.0016 (12)	0.0052 (13)
C12	0.0199 (12)	0.0379 (14)	0.0438 (16)	−0.0053 (10)	0.0046 (11)	−0.0043 (12)
C13	0.0272 (14)	0.0428 (16)	0.063 (2)	−0.0035 (11)	0.0099 (13)	−0.0097 (15)
C14	0.0245 (13)	0.0457 (16)	0.0491 (17)	−0.0017 (11)	0.0087 (12)	−0.0088 (13)
C15	0.0341 (14)	0.0463 (16)	0.0402 (16)	−0.0064 (12)	0.0046 (12)	−0.0023 (13)
C16	0.0328 (15)	0.0582 (19)	0.0359 (16)	−0.0070 (14)	−0.0038 (12)	0.0000 (13)
C17	0.0299 (14)	0.0512 (17)	0.0430 (16)	−0.0085 (12)	−0.0003 (13)	0.0016 (14)
C18	0.0399 (15)	0.0504 (17)	0.0353 (15)	−0.0053 (13)	−0.0007 (12)	−0.0038 (13)
C19	0.0298 (13)	0.0329 (13)	0.0395 (15)	0.0017 (10)	−0.0011 (11)	−0.0022 (11)
C20	0.0276 (14)	0.0416 (15)	0.0448 (16)	−0.0018 (11)	−0.0062 (12)	−0.0023 (13)

Geometric parameters (Å, º) top

Pd1—N1ⁱ	2.328 (2)	C7—H7	0.93
Pd1—N1	2.328 (2)	C8—C9	1.373 (4)
Pd1—O2	2.339 (2)	C8—H8	0.93
Pd1—O2ⁱ	2.339 (2)	C9—C12	1.389 (4)
Pd1—N2	2.340 (2)	C9—H9	0.93
Pd1—N2ⁱ	2.340 (2)	C10—C11	1.367 (4)
S1—O1B	1.396 (6)	C10—H10	0.93
S1—O2	1.442 (2)	C11—C12	1.397 (4)
S1—O3	1.473 (3)	C11—H11	0.93
S1—O1A	1.59 (4)	C12—C13	1.508 (4)
S1—C5	1.791 (3)	C13—C14	1.517 (3)
N1—C8	1.348 (3)	C13—H13A	0.97
N1—C10	1.349 (3)	C13—H13B	0.97
N2—C16	1.338 (3)	C14—C20ⁱⁱ	1.516 (4)
N2—C15	1.350 (4)	C14—H14A	0.97
C1—C2	1.535 (5)	C14—H14B	0.97
C1—H1A	0.96	C15—C18	1.366 (4)
C1—H1B	0.96	C15—H15	0.93
C1—H1C	0.96	C16—C17	1.374 (4)
C2—C7	1.367 (5)	C16—H16	0.93
C2—C3	1.369 (6)	C17—C19	1.392 (4)
C3—C4	1.382 (5)	C17—H17	0.93
C3—H3	0.93	C18—C19	1.392 (4)
C4—C5	1.365 (4)	C18—H18	0.93
C4—H4	0.93	C19—C20	1.496 (3)
C5—C6	1.388 (4)	C20—C14ⁱⁱⁱ	1.516 (4)
C6—C7	1.394 (5)	C20—H20A	0.97
C6—H6	0.93	C20—H20B	0.97

N1ⁱ—Pd1—N1	87.57 (10)	C2—C7—C6	122.1 (3)
N1ⁱ—Pd1—O2	90.82 (8)	C2—C7—H7	119
N1—Pd1—O2	89.13 (8)	C6—C7—H7	119
N1ⁱ—Pd1—O2ⁱ	89.13 (8)	N1—C8—C9	123.6 (3)
N1—Pd1—O2ⁱ	90.82 (8)	N1—C8—H8	118.2
O2—Pd1—O2ⁱ	179.93 (11)	C9—C8—H8	118.2
N1ⁱ—Pd1—N2	178.41 (7)	C8—C9—C12	119.7 (3)
N1—Pd1—N2	93.24 (8)	C8—C9—H9	120.2
O2—Pd1—N2	87.83 (8)	C12—C9—H9	120.2
O2ⁱ—Pd1—N2	92.23 (8)	N1—C10—C11	123.0 (2)
N1ⁱ—Pd1—N2ⁱ	93.24 (8)	N1—C10—H10	118.5
N1—Pd1—N2ⁱ	178.41 (7)	C11—C10—H10	118.5
O2—Pd1—N2ⁱ	92.23 (8)	C10—C11—C12	120.4 (2)
O2ⁱ—Pd1—N2ⁱ	87.83 (8)	C10—C11—H11	119.8
N2—Pd1—N2ⁱ	85.97 (10)	C12—C11—H11	119.8
O1B—S1—O2	121.7 (8)	C9—C12—C11	116.7 (2)
O1B—S1—O3	106.7 (11)	C9—C12—C13	121.1 (3)
O2—S1—O3	108.33 (16)	C11—C12—C13	122.2 (3)
O2—S1—O1A	92 (2)	C12—C13—C14	112.3 (2)
O3—S1—O1A	142 (2)	C12—C13—H13A	109.2
O1B—S1—C5	107.4 (4)	C14—C13—H13A	109.2
O2—S1—C5	106.20 (14)	C12—C13—H13B	109.2
O3—S1—C5	105.37 (15)	C14—C13—H13B	109.2
O1A—S1—C5	98.6 (8)	H13A—C13—H13B	107.9
S1—O2—Pd1	157.82 (15)	C20ⁱⁱ—C14—C13	113.3 (2)
C8—N1—C10	116.6 (2)	C20ⁱⁱ—C14—H14A	108.9
C8—N1—Pd1	126.37 (17)	C13—C14—H14A	108.9
C10—N1—Pd1	116.20 (17)	C20ⁱⁱ—C14—H14B	108.9
C16—N2—C15	117.2 (2)	C13—C14—H14B	108.9
C16—N2—Pd1	115.22 (18)	H14A—C14—H14B	107.7
C15—N2—Pd1	126.96 (18)	N2—C15—C18	123.4 (3)
C2—C1—H1A	109.5	N2—C15—H15	118.3
C2—C1—H1B	109.5	C18—C15—H15	118.3
H1A—C1—H1B	109.5	N2—C16—C17	122.6 (3)
C2—C1—H1C	109.5	N2—C16—H16	118.7
H1A—C1—H1C	109.5	C17—C16—H16	118.7
H1B—C1—H1C	109.5	C16—C17—C19	120.4 (3)
C7—C2—C3	117.1 (3)	C16—C17—H17	119.8
C7—C2—C1	121.0 (5)	C19—C17—H17	119.8
C3—C2—C1	121.9 (5)	C15—C18—C19	119.7 (3)
C2—C3—C4	121.9 (3)	C15—C18—H18	120.2
C2—C3—H3	119	C19—C18—H18	120.2
C4—C3—H3	119	C17—C19—C18	116.7 (2)
C5—C4—C3	121.0 (3)	C17—C19—C20	122.7 (2)
C5—C4—H4	119.5	C18—C19—C20	120.5 (2)
C3—C4—H4	119.5	C19—C20—C14ⁱⁱⁱ	114.7 (2)
C4—C5—C6	118.1 (3)	C19—C20—H20A	108.6
C4—C5—S1	120.3 (2)	C14ⁱⁱⁱ—C20—H20A	108.6
C6—C5—S1	121.5 (2)	C19—C20—H20B	108.6
C5—C6—C7	119.8 (3)	C14ⁱⁱⁱ—C20—H20B	108.6
C5—C6—H6	120.1	H20A—C20—H20B	107.6
C7—C6—H6	120.1

O1B—S1—O2—Pd1	−103.6 (11)	O3—S1—C5—C6	169.7 (2)
O3—S1—O2—Pd1	20.5 (5)	O1A—S1—C5—C6	−40 (3)
O1A—S1—O2—Pd1	−127.1 (14)	C4—C5—C6—C7	−1.3 (4)
C5—S1—O2—Pd1	133.3 (4)	S1—C5—C6—C7	174.4 (2)
N1ⁱ—Pd1—O2—S1	91.8 (4)	C3—C2—C7—C6	1.1 (5)
N1—Pd1—O2—S1	179.3 (4)	C1—C2—C7—C6	−177.4 (4)
N2—Pd1—O2—S1	−87.4 (4)	C5—C6—C7—C2	0.0 (5)
N2ⁱ—Pd1—O2—S1	−1.5 (4)	C10—N1—C8—C9	2.2 (4)
N1ⁱ—Pd1—N1—C8	−127.0 (2)	Pd1—N1—C8—C9	−166.94 (19)
O2—Pd1—N1—C8	142.2 (2)	N1—C8—C9—C12	−0.9 (4)
O2ⁱ—Pd1—N1—C8	−37.9 (2)	C8—N1—C10—C11	−1.7 (4)
O2—Pd1—N1—C10	−27.1 (2)	Pd1—N1—C10—C11	168.6 (2)
O2ⁱ—Pd1—N1—C10	152.9 (2)	N1—C10—C11—C12	−0.2 (4)
N2—Pd1—N1—C10	−114.83 (19)	C8—C9—C12—C11	−1.0 (4)
N1—Pd1—N2—C16	128.3 (2)	C8—C9—C12—C13	178.5 (2)
O2ⁱ—Pd1—N2—C16	−140.8 (2)	C10—C11—C12—C9	1.5 (4)
N2ⁱ—Pd1—N2—C16	−53.09 (18)	C10—C11—C12—C13	−178.0 (3)
N1—Pd1—N2—C15	−61.2 (2)	C9—C12—C13—C14	78.7 (3)
O2—Pd1—N2—C15	−150.2 (2)	C11—C12—C13—C14	−101.9 (3)
O2ⁱ—Pd1—N2—C15	29.7 (2)	C12—C13—C14—C20ⁱⁱ	72.0 (3)
N2ⁱ—Pd1—N2—C15	117.4 (2)	C16—N2—C15—C18	−0.1 (4)
C7—C2—C3—C4	−0.9 (6)	Pd1—N2—C15—C18	−170.4 (2)
C1—C2—C3—C4	177.5 (4)	C15—N2—C16—C17	0.6 (4)
C2—C3—C4—C5	−0.4 (6)	Pd1—N2—C16—C17	172.0 (2)
C3—C4—C5—C6	1.5 (5)	N2—C16—C17—C19	−1.3 (5)
C3—C4—C5—S1	−174.3 (3)	N2—C15—C18—C19	0.3 (4)
O1B—S1—C5—C4	98.9 (12)	C16—C17—C19—C18	1.4 (4)
O2—S1—C5—C4	−129.5 (2)	C16—C17—C19—C20	−178.2 (3)
O3—S1—C5—C4	−14.7 (3)	C15—C18—C19—C17	−0.9 (4)
O1A—S1—C5—C4	136 (3)	C15—C18—C19—C20	178.6 (2)
O1B—S1—C5—C6	−76.7 (12)	C17—C19—C20—C14ⁱⁱⁱ	0.2 (4)
O2—S1—C5—C6	54.9 (3)	C18—C19—C20—C14ⁱⁱⁱ	−179.3 (2)

Symmetry codes: (i) x, −y+1/2, −z+1/2; (ii) x+1/2, y, −z; (iii) x−1/2, y, −z.

Experimental details

Crystal data
Chemical formula	[Pd(C₇H₇O₃S)₂(C₁₃H₁₄N₂)₂]
M_r	845.3
Crystal system, space group	Orthorhombic, Pnna
Temperature (K)	273
a, b, c (Å)	23.818 (2), 17.4359 (10), 9.3341 (10)
V (Å³)	3876.3 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.64
Crystal size (mm)	0.12 × 0.08 × 0.01

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.927, 0.994
No. of measured, independent and observed [I > 2σ(I)] reflections	18799, 3374, 2761
R_int	0.068
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.091, 1.08
No. of reflections	3374
No. of parameters	251
H-atom treatment	H-atom parameters not refined
Δρ_max, Δρ_min (e Å⁻³)	0.61, −0.67

Computer programs: APEX2 (Bruker, 2004), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

The authors thank the NSFC (grant No. 20776081) and the Natural Science Foundation of Shandong Province (grant No. Y2006B37).

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