[μ-N,N,N′,N′-Tetra­kis(diphenyl­phosphino­meth­yl)benzene-1,4-diamine-κ4P,P′:P′′,P′′′]bis­[bis­(nitrato-κO)palladium(II)]

Jiang, X.-F.; Lian, H.-C.; Min, Z.; Wang, X.-J.; Lin, J.-H.

doi:10.1107/S160053680901486X

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 5| May 2009| Pages m597-m598

doi:10.1107/S160053680901486X

Open

access

[μ-N,N,N′,N′-Tetrakis(diphenylphosphinomethyl)benzene-1,4-diamine-κ⁴P,P′:P′′,P′′′]bis[bis(nitrato-κO)palladium(II)]

Xuan-Feng Jiang,^a Heng-Chi Lian,^a Zhong Min,^a Xiu-Jian Wang ^a ^* and Jia-Huang Lin ^a

^aSchool of Chemistry and Chemical Engineering, Guangxi Normal University, Guilin 541004, People's Republic of China
^*Correspondence e-mail: wang1_xj@yahoo.com.cn

(Received 26 March 2009; accepted 22 April 2009; online 30 April 2009)

The asymmetric unit of the title complex, [Pd₂(NO₃)₄(C₅₈H₅₂N₂P₄)], contains one half-molecule, in which the central benzene ring is located on a crystallographic centre of inversion. The Pd atom has a distorted square-planar coordination consisting of two P and two O atoms. In the crystal structure, intermolecular C—H⋯O interactions link the molecules into chains, and π–π contacts between the phenyl rings [centroid–centroid distance = 3.928 (3) Å] may further stabilize the structure.

Related literature

For related structures, see: Aucott et al. (2002 ); Ganesamoorthy et al. (2008 ); Wang et al. (2008 ). For bond-length data, see: Allen et al. (1987 ). For ring-puckering parameters, see: Cremer & Pople (1975 ).

Experimental

Crystal data

[Pd₂(NO₃)₄(C₅₈H₅₂N₂P₄)]
M_r = 1361.74
Monoclinic, P 2₁ /n
a = 8.0715 (2) Å
b = 21.3419 (7) Å
c = 16.0283 (5) Å
β = 92.937 (3)°
V = 2757.43 (14) Å³
Z = 2
Mo Kα radiation
μ = 0.84 mm⁻¹
T = 294 K
0.40 × 0.15 × 0.15 mm

Data collection

Oxford Diffraction Gemini S Untra diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.773, T_max = 0.882
13871 measured reflections
6838 independent reflections
3511 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.072
S = 0.80
6838 reflections
370 parameters
H-atom parameters constrained
Δρ_max = 1.04 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Pd1—P1	2.2198 (7)
Pd1—P2	2.2087 (9)
Pd1—O3	2.144 (2)
Pd1—O6	2.1377 (17)

P2—Pd1—P1	92.34 (3)
O3—Pd1—P1	89.72 (5)
O3—Pd1—P2	177.92 (5)
O3—Pd1—O6	91.77 (8)
O6—Pd1—P1	173.04 (6)
O6—Pd1—P2	86.15 (6)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4B⋯O5ⁱ	0.97	2.31	3.248 (3)	163
Symmetry code: (i) x-1, y, z.

Data collection: CrysAlis CCD (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); data reduction: CrysAlis RED; 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680901486X/hk2653sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680901486X/hk2653Isup2.hkl

checkCIF report

Comment top

The potential applications as catalysts of palladium(II) complexes, containing phosphine ligands, had been extensively studied so far. A lot of analogs were reported (Aucott et al., 2002; Ganesamoorthy et al., 2008; Wang et al., 2008), and some of them are catalytically active in homogeneous hydrogenations and in other organic reactions. We report herein the crystal structure of the title complex.

The asymmetric unit of the title complex contains one-half molecule (Fig. 1), in which the central benzene ring is located on a crystallographic centre of inversion. The Pd atom is in a distorted square-planar coordination by two P and two O atoms. The Pd-P and Pd-O bond lengths (Allen et al., 1987) and angles (Table 1) are within normal ranges. Rings A (C5-C10), B (C11-C16), C (C18-C23) and D (C24-C29) are, of course, planar and they are oriented at dihedral angles of A/B = 64.08 (3), A/C = 17.77 (3), A/D = 78.70 (3), B/C = 64.54 (3) and B/D = 27.80 (3) °. Ring E (Pd1/P1/P2/N1/C4/C17) is not planar, having total puckering amplitude, Q_T, of 2.670 (2) Å and twisted conformation [ϕ = -88.23 (3) and θ = 100.40 (3) °] (Cremer & Pople, 1975).

In the crystal structure, intermolecular C-H···O interactions (Table 2) link the molecules into chains, in which they may be effective in the stabilization of the structure. The π–π contact between the phenyl rings, Cg2—Cg4ⁱ [symmetry code: (i) 1/2 + x, 1/2 - y, z + 1/2, where Cg2 and Cg4 are centroids of the rings B (C11-C16) and D (C24-C29), respectively] may further stabilize the structure, with centroid-centroid distance of 3.928 (3) Å.

Related literature top

For related structures, see: Aucott et al. (2002); Ganesamoorthy et al. (2008); Wang et al. (2008). For bond-length data, see: Allen et al. (1987). For ring-puckering parameters, see: Cremer & Pople (1975).

Experimental top

For the preparation of the title complex, PdCl₂(0.0350 g, 0.2 mmol) in CH₃CN (10 ml) was stirred at 348-353 K for 4 h, until the solid palladium salt was dissolved completely to give a yellow solution. Then, the liquor was cooled to about 277 K for a few hours, and the yellow precipitate, Pd(CH₃CN)₂Cl₂, was collected by filtration. Then, Pd(CH₃CN)₂Cl₂ (0.0265 g, 0.1 mmol) in CH₃CN (5 ml) was stirred at room temperature for 20 min, and AgNO₃ (0.0345 g, 0.2 mmol) in DMF (5 ml) was added dropwise with stirring. A pale precipitate of AgCl formed and the solution was filtered, The phosphine ligand, (L), (0.0450 g, 0.05 mmol) was added until the color of solution turned to red, and then the stirring is continued for 2 h. After filtration, diffusion of diethyl ether at room temperature into the solution the yellow crystals of the title complex, [Pd₂(L)(NO₃)₄], were obtained.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2007); cell refinement: CrysAlis RED (Oxford Diffraction, 2007); data reduction: CrysAlis RED (Oxford Diffraction, 2007); 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 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme [symmetry code ('): -x, -y, -z].

[µ-N,N,N',N'-Tetrakis(diphenylphosphinomethyl)benzene- 1,4-diamine-κ⁴P/i>,P/i>':P/i>'',P/i>''']bis[bis(nitrato- κO)palladium(II)] top

Crystal data top

[Pd₂(NO₃)₄(C₅₈H₅₂N₂P₄)]	F(000) = 1380
M_r = 1361.74	D_x = 1.640 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4249 reflections
a = 8.0715 (2) Å	θ = 11.3–28.6°
b = 21.3419 (7) Å	µ = 0.84 mm⁻¹
c = 16.0283 (5) Å	T = 294 K
β = 92.937 (3)°	Block, yellow
V = 2757.43 (14) Å³	0.4 × 0.15 × 0.15 mm
Z = 2

Data collection top

Gemini S Untra diffractometer	6838 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3511 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
Detector resolution: 16.0855 pixels mm^-1	θ_max = 30.2°, θ_min = 2.8°
ω scans	h = −11→9
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	k = −28→27
T_min = 0.773, T_max = 0.882	l = −22→21
13871 measured reflections

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.072	H-atom parameters constrained
S = 0.80	w = 1/[σ²(F_o²) + (0.0313P)²] where P = (F_o² + 2F_c²)/3
6838 reflections	(Δ/σ)_max = 0.004
370 parameters	Δρ_max = 1.04 e Å⁻³
0 restraints	Δρ_min = −0.37 e Å⁻³

Crystal data top

[Pd₂(NO₃)₄(C₅₈H₅₂N₂P₄)]	V = 2757.43 (14) Å³
M_r = 1361.74	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.0715 (2) Å	µ = 0.84 mm⁻¹
b = 21.3419 (7) Å	T = 294 K
c = 16.0283 (5) Å	0.4 × 0.15 × 0.15 mm
β = 92.937 (3)°

Data collection top

Gemini S Untra diffractometer	6838 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	3511 reflections with I > 2σ(I)
T_min = 0.773, T_max = 0.882	R_int = 0.035
13871 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.072	H-atom parameters constrained
S = 0.80	Δρ_max = 1.04 e Å⁻³
6838 reflections	Δρ_min = −0.37 e Å⁻³
370 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
Pd1	1.39486 (3)	1.789182 (12)	0.214196 (13)	0.02504 (8)
P1	1.22599 (9)	1.78487 (4)	0.10059 (4)	0.02366 (18)
P2	1.30017 (9)	1.88209 (4)	0.24940 (5)	0.02471 (19)
O1	1.4811 (3)	1.60188 (12)	0.22173 (15)	0.0613 (8)
O2	1.3721 (3)	1.67330 (12)	0.29761 (14)	0.0461 (6)
O3	1.4938 (2)	1.69934 (10)	0.18353 (12)	0.0311 (5)
O4	1.8332 (3)	1.83114 (12)	0.33338 (14)	0.0518 (7)
O5	1.7301 (3)	1.81444 (13)	0.20792 (14)	0.0486 (7)
O6	1.5755 (2)	1.80091 (10)	0.31524 (11)	0.0298 (5)
N1	1.0910 (3)	1.90013 (12)	0.11125 (14)	0.0271 (6)
N2	1.4459 (3)	1.65651 (15)	0.23480 (18)	0.0391 (7)
N3	1.7185 (3)	1.81587 (13)	0.28399 (18)	0.0372 (7)
C1	0.9830 (3)	1.93941 (14)	−0.02623 (17)	0.0299 (8)
H1A	0.9729	1.8985	−0.0457	0.036*
C2	1.0433 (3)	1.94993 (14)	0.05573 (16)	0.0240 (7)
C3	1.0617 (3)	2.01198 (14)	0.07878 (18)	0.0286 (8)
H3A	1.1061	2.0212	0.1320	0.034*
C4	1.0437 (3)	1.83578 (14)	0.09201 (17)	0.0264 (7)
H4A	0.9936	1.8335	0.0358	0.032*
H4B	0.9624	1.8217	0.1304	0.032*
C5	1.3384 (3)	1.80561 (14)	0.00986 (17)	0.0264 (7)
C6	1.5000 (4)	1.82739 (15)	0.0189 (2)	0.0352 (8)
H6A	1.5527	1.8304	0.0717	0.042*
C7	1.5828 (4)	1.84462 (17)	−0.0511 (2)	0.0417 (9)
H7A	1.6916	1.8589	−0.0451	0.050*
C8	1.5067 (4)	1.84081 (16)	−0.1282 (2)	0.0390 (8)
H8A	1.5637	1.8523	−0.1748	0.047*
C9	1.3461 (4)	1.82008 (16)	−0.1380 (2)	0.0378 (9)
H9A	1.2945	1.8180	−0.1911	0.045*
C10	1.2609 (4)	1.80238 (15)	−0.06993 (18)	0.0321 (8)
H10A	1.1520	1.7883	−0.0769	0.039*
C11	1.1447 (3)	1.70636 (15)	0.08770 (17)	0.0249 (7)
C12	1.2026 (4)	1.66574 (15)	0.02931 (19)	0.0305 (8)
H12A	1.2794	1.6793	−0.0081	0.037*
C13	1.1461 (5)	1.60480 (16)	0.0265 (2)	0.0422 (9)
H13A	1.1848	1.5774	−0.0132	0.051*
C14	1.0363 (4)	1.58451 (16)	0.0802 (2)	0.0438 (9)
H14A	0.9999	1.5432	0.0776	0.053*
C15	0.9767 (5)	1.62465 (18)	0.1396 (2)	0.0497 (10)
H15A	0.8998	1.6104	0.1765	0.060*
C16	1.0314 (4)	1.68549 (16)	0.1437 (2)	0.0387 (9)
H16A	0.9928	1.7126	0.1839	0.046*
C17	1.1050 (3)	1.91098 (15)	0.20009 (16)	0.0267 (7)
H17A	1.0131	1.8906	0.2258	0.032*
H17B	1.0963	1.9556	0.2105	0.032*
C18	1.4595 (4)	1.93885 (15)	0.23045 (18)	0.0279 (7)
C19	1.4731 (4)	1.96391 (15)	0.15109 (19)	0.0353 (8)
H19A	1.3939	1.9545	0.1088	0.042*
C20	1.6040 (4)	2.00260 (17)	0.1352 (2)	0.0411 (9)
H20A	1.6123	2.0196	0.0822	0.049*
C21	1.7229 (4)	2.01633 (16)	0.1973 (2)	0.0404 (9)
H21A	1.8105	2.0429	0.1863	0.048*
C22	1.7118 (4)	1.99062 (17)	0.2755 (2)	0.0398 (9)
H22A	1.7926	1.9995	0.3172	0.048*
C23	1.5816 (4)	1.95192 (15)	0.29200 (19)	0.0348 (8)
H23A	1.5752	1.9344	0.3448	0.042*
C24	1.2525 (3)	1.88447 (15)	0.35784 (17)	0.0258 (7)
C25	1.2340 (4)	1.83006 (16)	0.40314 (18)	0.0320 (8)
H25A	1.2617	1.7917	0.3802	0.038*
C26	1.1751 (4)	1.83253 (18)	0.4817 (2)	0.0410 (9)
H26A	1.1623	1.7957	0.5117	0.049*
C27	1.1346 (4)	1.8891 (2)	0.5166 (2)	0.0490 (10)
H27A	1.0932	1.8903	0.5696	0.059*
C28	1.1551 (4)	1.9432 (2)	0.4734 (2)	0.0479 (10)
H28A	1.1301	1.9814	0.4976	0.058*
C29	1.2133 (4)	1.94164 (17)	0.39349 (19)	0.0374 (8)
H29A	1.2260	1.9787	0.3639	0.045*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pd1	0.02445 (13)	0.02725 (13)	0.02345 (13)	0.00320 (13)	0.00145 (9)	0.00167 (13)
P1	0.0258 (4)	0.0238 (4)	0.0215 (4)	0.0005 (4)	0.0019 (3)	0.0011 (4)
P2	0.0240 (4)	0.0260 (5)	0.0242 (4)	0.0002 (4)	0.0017 (3)	0.0016 (4)
O1	0.092 (2)	0.0341 (16)	0.0588 (17)	0.0263 (16)	0.0099 (14)	0.0110 (14)
O2	0.0473 (15)	0.0508 (17)	0.0411 (15)	0.0053 (13)	0.0123 (12)	0.0066 (13)
O3	0.0336 (12)	0.0306 (13)	0.0294 (12)	0.0073 (11)	0.0068 (9)	0.0021 (11)
O4	0.0329 (14)	0.0729 (19)	0.0481 (15)	−0.0094 (14)	−0.0126 (11)	0.0088 (14)
O5	0.0395 (14)	0.078 (2)	0.0293 (13)	−0.0059 (14)	0.0083 (10)	0.0091 (13)
O6	0.0195 (11)	0.0434 (15)	0.0266 (11)	0.0012 (11)	0.0019 (8)	0.0020 (10)
N1	0.0311 (15)	0.0222 (14)	0.0275 (14)	0.0011 (13)	−0.0017 (11)	−0.0015 (12)
N2	0.0383 (17)	0.044 (2)	0.0356 (18)	0.0165 (16)	0.0058 (13)	0.0134 (17)
N3	0.0301 (17)	0.0392 (17)	0.0421 (18)	0.0000 (14)	−0.0012 (14)	0.0075 (15)
C1	0.0334 (18)	0.0218 (17)	0.0339 (18)	0.0022 (15)	−0.0028 (14)	−0.0037 (15)
C2	0.0243 (17)	0.0253 (17)	0.0226 (17)	0.0047 (15)	0.0042 (13)	0.0035 (15)
C3	0.0331 (18)	0.0288 (19)	0.0235 (16)	0.0015 (16)	−0.0044 (13)	−0.0022 (15)
C4	0.0241 (17)	0.0296 (18)	0.0258 (17)	0.0001 (15)	0.0036 (13)	0.0042 (15)
C5	0.0266 (17)	0.0259 (18)	0.0268 (17)	0.0001 (14)	0.0038 (13)	0.0016 (14)
C6	0.035 (2)	0.035 (2)	0.0363 (19)	0.0006 (18)	0.0026 (15)	0.0065 (17)
C7	0.035 (2)	0.050 (2)	0.040 (2)	−0.0088 (19)	0.0065 (16)	0.0088 (19)
C8	0.042 (2)	0.044 (2)	0.0331 (19)	−0.0032 (19)	0.0169 (15)	0.0040 (17)
C9	0.048 (2)	0.034 (2)	0.0313 (19)	0.0001 (19)	0.0014 (16)	0.0023 (17)
C10	0.0289 (17)	0.036 (2)	0.0320 (18)	−0.0045 (16)	0.0041 (14)	0.0015 (16)
C11	0.0276 (17)	0.0246 (17)	0.0222 (15)	0.0014 (16)	−0.0017 (13)	0.0026 (16)
C12	0.0293 (18)	0.0280 (19)	0.0346 (18)	0.0013 (16)	0.0043 (14)	0.0048 (17)
C13	0.063 (3)	0.024 (2)	0.039 (2)	0.0072 (19)	0.0000 (18)	−0.0046 (18)
C14	0.064 (3)	0.0213 (19)	0.045 (2)	−0.0073 (19)	−0.0067 (19)	0.0044 (18)
C15	0.066 (3)	0.043 (2)	0.042 (2)	−0.018 (2)	0.0138 (18)	0.008 (2)
C16	0.049 (2)	0.032 (2)	0.035 (2)	−0.0066 (18)	0.0085 (16)	0.0010 (17)
C17	0.0216 (16)	0.0277 (18)	0.0310 (18)	0.0059 (15)	0.0035 (13)	0.0050 (15)
C18	0.0253 (17)	0.0257 (18)	0.0328 (18)	0.0046 (15)	0.0016 (13)	−0.0034 (15)
C19	0.0320 (19)	0.033 (2)	0.041 (2)	−0.0028 (17)	0.0057 (15)	0.0012 (17)
C20	0.038 (2)	0.041 (2)	0.045 (2)	0.0015 (19)	0.0106 (16)	0.0052 (18)
C21	0.037 (2)	0.029 (2)	0.056 (2)	−0.0055 (17)	0.0153 (17)	−0.0056 (19)
C22	0.0274 (19)	0.039 (2)	0.054 (2)	−0.0034 (17)	0.0044 (15)	−0.0153 (19)
C23	0.040 (2)	0.034 (2)	0.0301 (18)	0.0011 (17)	0.0053 (15)	−0.0023 (17)
C24	0.0182 (16)	0.0330 (19)	0.0260 (16)	−0.0040 (15)	0.0005 (12)	0.0046 (16)
C25	0.0304 (18)	0.039 (2)	0.0266 (18)	−0.0057 (17)	0.0020 (14)	−0.0024 (17)
C26	0.042 (2)	0.048 (3)	0.032 (2)	−0.017 (2)	0.0028 (16)	0.0041 (19)
C27	0.044 (2)	0.072 (3)	0.032 (2)	−0.018 (2)	0.0144 (16)	−0.014 (2)
C28	0.044 (2)	0.055 (3)	0.046 (2)	−0.002 (2)	0.0145 (17)	−0.013 (2)
C29	0.038 (2)	0.039 (2)	0.036 (2)	−0.0014 (18)	0.0014 (15)	0.0011 (18)

Geometric parameters (Å, º) top

Pd1—P1	2.2198 (7)	C10—H10A	0.9300
Pd1—P2	2.2087 (9)	C11—C12	1.375 (4)
Pd1—O3	2.144 (2)	C11—C16	1.388 (4)
Pd1—O6	2.1377 (17)	C12—C13	1.378 (4)
P1—C4	1.829 (3)	C12—H12A	0.9300
P1—C5	1.808 (3)	C13—C14	1.338 (5)
P1—C11	1.807 (3)	C13—H13A	0.9300
P2—C17	1.833 (3)	C14—C15	1.385 (5)
P2—C18	1.803 (3)	C14—H14A	0.9300
P2—C24	1.800 (3)	C15—C16	1.372 (5)
O1—N2	1.221 (4)	C15—H15A	0.9300
O2—N2	1.248 (3)	C16—H16A	0.9300
O3—N2	1.301 (3)	C17—H17A	0.9700
O4—N3	1.231 (3)	C17—H17B	0.9700
O5—N3	1.228 (3)	C18—C19	1.389 (4)
O6—N3	1.320 (3)	C18—C23	1.387 (4)
N1—C2	1.426 (3)	C19—C20	1.375 (4)
N1—C4	1.454 (4)	C19—H19A	0.9300
N1—C17	1.441 (3)	C20—C21	1.378 (4)
C1—C2	1.396 (4)	C20—H20A	0.9300
C1—C3ⁱ	1.373 (4)	C21—C22	1.376 (4)
C1—H1A	0.9300	C21—H21A	0.9300
C2—C3	1.381 (4)	C22—C23	1.373 (4)
C3—C1ⁱ	1.373 (4)	C22—H22A	0.9300
C3—H3A	0.9300	C23—H23A	0.9300
C4—H4A	0.9700	C24—C25	1.381 (4)
C4—H4B	0.9700	C24—C29	1.391 (4)
C5—C6	1.386 (4)	C25—C26	1.370 (4)
C5—C10	1.396 (4)	C25—H25A	0.9300
C6—C7	1.384 (4)	C26—C27	1.376 (5)
C6—H6A	0.9300	C26—H26A	0.9300
C7—C8	1.354 (4)	C27—C28	1.360 (5)
C7—H7A	0.9300	C27—H27A	0.9300
C8—C9	1.371 (4)	C28—C29	1.387 (4)
C8—H8A	0.9300	C28—H28A	0.9300
C9—C10	1.372 (4)	C29—H29A	0.9300
C9—H9A	0.9300

P2—Pd1—P1	92.34 (3)	C9—C10—H10A	120.2
O3—Pd1—P1	89.72 (5)	C12—C11—P1	121.9 (2)
O3—Pd1—P2	177.92 (5)	C12—C11—C16	119.8 (3)
O3—Pd1—O6	91.77 (8)	C16—C11—P1	118.1 (2)
O6—Pd1—P1	173.04 (6)	C11—C12—C13	119.6 (3)
O6—Pd1—P2	86.15 (6)	C11—C12—H12A	120.2
C4—P1—Pd1	119.67 (10)	C13—C12—H12A	120.2
C5—P1—Pd1	109.72 (9)	C12—C13—H13A	119.5
C5—P1—C4	103.24 (13)	C14—C13—C12	120.9 (3)
C11—P1—Pd1	109.65 (9)	C14—C13—H13A	119.5
C11—P1—C4	104.84 (13)	C13—C14—C15	120.4 (3)
C11—P1—C5	109.21 (14)	C13—C14—H14A	119.8
C17—P2—Pd1	119.53 (10)	C15—C14—H14A	119.8
C18—P2—Pd1	107.51 (10)	C14—C15—H15A	120.1
C18—P2—C17	107.81 (14)	C16—C15—C14	119.8 (3)
C24—P2—Pd1	111.46 (11)	C16—C15—H15A	120.1
C24—P2—C17	100.67 (13)	C11—C16—H16A	120.2
C24—P2—C18	109.47 (14)	C15—C16—C11	119.6 (3)
N2—O3—Pd1	110.94 (18)	C15—C16—H16A	120.2
N3—O6—Pd1	108.45 (16)	P2—C17—H17A	108.9
C2—N1—C4	120.8 (2)	P2—C17—H17B	108.9
C2—N1—C17	120.1 (2)	N1—C17—P2	113.2 (2)
C17—N1—C4	111.6 (2)	N1—C17—H17A	108.9
O1—N2—O2	122.5 (3)	N1—C17—H17B	108.9
O1—N2—O3	118.9 (3)	H17A—C17—H17B	107.7
O2—N2—O3	118.5 (3)	C19—C18—P2	120.2 (2)
O4—N3—O5	123.5 (3)	C23—C18—P2	120.1 (2)
O4—N3—O6	117.6 (3)	C23—C18—C19	119.1 (3)
O5—N3—O6	118.9 (2)	C18—C19—H19A	120.0
C2—C1—H1A	119.2	C20—C19—C18	119.9 (3)
C3ⁱ—C1—C2	121.6 (3)	C20—C19—H19A	120.0
C3ⁱ—C1—H1A	119.2	C19—C20—C21	120.5 (3)
C1—C2—N1	122.5 (3)	C19—C20—H20A	119.8
C3—C2—C1	115.7 (3)	C21—C20—H20A	119.8
C3—C2—N1	121.7 (2)	C20—C21—H21A	120.1
C1ⁱ—C3—C2	122.6 (3)	C22—C21—C20	119.8 (3)
C1ⁱ—C3—H3A	118.7	C22—C21—H21A	120.1
C2—C3—H3A	118.7	C21—C22—H22A	119.9
P1—C4—H4A	109.6	C23—C22—C21	120.1 (3)
P1—C4—H4B	109.6	C23—C22—H22A	119.9
N1—C4—P1	110.08 (19)	C18—C23—H23A	119.8
N1—C4—H4A	109.6	C22—C23—C18	120.5 (3)
N1—C4—H4B	109.6	C22—C23—H23A	119.8
H4A—C4—H4B	108.2	C25—C24—C29	119.3 (3)
C6—C5—P1	120.5 (2)	C25—C24—P2	121.2 (2)
C6—C5—C10	119.2 (3)	C29—C24—P2	119.1 (2)
C10—C5—P1	120.3 (2)	C24—C25—H25A	119.9
C5—C6—H6A	120.1	C26—C25—C24	120.2 (3)
C7—C6—C5	119.7 (3)	C26—C25—H25A	119.9
C7—C6—H6A	120.1	C25—C26—C27	120.5 (4)
C6—C7—H7A	119.7	C25—C26—H26A	119.8
C8—C7—C6	120.5 (3)	C27—C26—H26A	119.8
C8—C7—H7A	119.7	C26—C27—H27A	120.0
C7—C8—C9	120.4 (3)	C28—C27—C26	120.0 (3)
C7—C8—H8A	119.8	C28—C27—H27A	120.0
C9—C8—H8A	119.8	C27—C28—C29	120.4 (4)
C8—C9—C10	120.5 (3)	C27—C28—H28A	119.8
C8—C9—H9A	119.7	C29—C28—H28A	119.8
C10—C9—H9A	119.7	C24—C29—H29A	120.2
C5—C10—H10A	120.2	C28—C29—C24	119.7 (3)
C9—C10—C5	119.7 (3)	C28—C29—H29A	120.2

Symmetry code: (i) −x+2, −y+4, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4B···O5ⁱⁱ	0.97	2.31	3.248 (3)	163

Symmetry code: (ii) x−1, y, z.

Experimental details

Crystal data
Chemical formula	[Pd₂(NO₃)₄(C₅₈H₅₂N₂P₄)]
M_r	1361.74
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	294
a, b, c (Å)	8.0715 (2), 21.3419 (7), 16.0283 (5)
β (°)	92.937 (3)
V (Å³)	2757.43 (14)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.84
Crystal size (mm)	0.4 × 0.15 × 0.15

Data collection
Diffractometer	Gemini S Untra diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2007)
T_min, T_max	0.773, 0.882
No. of measured, independent and observed [I > 2σ(I)] reflections	13871, 6838, 3511
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.708

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.072, 0.80
No. of reflections	6838
No. of parameters	370
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.04, −0.37

Computer programs: CrysAlis CCD (Oxford Diffraction, 2007), CrysAlis RED (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Selected geometric parameters (Å, º) top

Pd1—P1	2.2198 (7)	Pd1—O3	2.144 (2)
Pd1—P2	2.2087 (9)	Pd1—O6	2.1377 (17)

P2—Pd1—P1	92.34 (3)	O3—Pd1—O6	91.77 (8)
O3—Pd1—P1	89.72 (5)	O6—Pd1—P1	173.04 (6)
O3—Pd1—P2	177.92 (5)	O6—Pd1—P2	86.15 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4B···O5ⁱ	0.97	2.31	3.248 (3)	163.00

Symmetry code: (i) x−1, y, z.

Acknowledgements

This work was supported by the Innovation Project of Guangxi Graduate Education, China (grant No. 2008106020703M246).

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Aucott, S. M., Slawin, A. M. Z. & Woollins, J. D. (2002). Eur. J. Inorg. Chem. pp. 2408–2418. CrossRef Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Ganesamoorthy, C., Balakrishna, M. S., Mague, J. T. & Tuononen, H. M. (2008). Inorg. Chem. 47 7035–7047. Web of Science CSD CrossRef PubMed CAS Google Scholar
Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, X.-J., Gui, L.-C., Ni, Q.-L., Liao, Y.-F., Jiang, X.-F., Tang, L.-H., Zhang, Z. & Wu, Q. (2008). CrystEngComm, 10, 1003–1010. Web of Science CSD CrossRef CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.