(Ethane 1,2 di­amine)dinitratopalladium(II)

metal-organic papers

m1940

2H8N4O6Pd doi:10.1107/S1600536805027224 Acta Cryst.(2005). E61, m1940–m1942 Acta Crystallographica Section E

Structure Reports

Online

ISSN 1600-5368

(Ethane-1,2-diamine)dinitratopalladium(II)

David J. Bray,a,bJack K. Clegg,b* Li-Ling Liao,c,bLeonard F. Lindoy,b John C. McMurtrie,d,b David Schilter,bGang Weia,band Tae-Jin Wonb

a_{CSIRO, Industrial Physics, Bradfield Road,}

West Lindfield, New South Wales 2070, Australia,bCentre for Heavy Metals Research, School of Chemistry, F11, The University of Sydney, NSW 2006, Australia,cSchool of Physics and Chemistry, Guizhou Normal University, Guiyang, Guizhou, People’s Republic of China, andd_{School of Physical and}

Chemical Sciences, Queensland University of Technology, Queensland 4001, Australia

Correspondence e-mail: [email protected]

Key indicators

Single-crystal X-ray study

T= 150 K

Mean(C–C) = 0.002 A˚

Rfactor = 0.016

wRfactor = 0.043

Data-to-parameter ratio = 15.0

For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.

#2005 International Union of Crystallography Printed in Great Britain – all rights reserved

The title compound, [Pd(NO3)2(C2H8N2)], forms an infinite

two-dimensional sheet-like motif, propagated by inter-molecular hydrogen bonds between the amino groups of the ethane-1,2-diamine ligands and the nitrate O atoms. There are two complex molecules in the asymmetric unit.

Comment

Our group has long been interested in the use of metal complexes as components for the construction of large supramolecular architectures (Lindoy & Atkinson, 2000). In particular, we are interested in the construction and chemistry of metallocyclic systems (Clegg et al., 2004, 2005). The title compound, (I), has found extensive use as a precursor in the preparation of cyclic metallo-supramolecular structures (Fujita et al., 2005). Crystals suitable for this study were obtained in the course of our investigation into the inter-actions of N-donor ligand systems (Brayet al., 2005) with (I).

An ORTEP(Farrugia, 1997) representation of (I) is given in Fig. 1. As expected, each PdIIion has a geometry close to an ideal square-plane (Table 1). The N donor atoms of the bidentate ethane-1,2-diamine ligand (en) occupy two coordi-nation sites in a typical five-membered chelate arrangment. The remaining coordination sites are occupied by nitrate O atoms of two nitrate ligands.

The asymmetric unit contains two of these complexes, which pack via intermolecular hydrogen bonds between the NH2

groups of the en ligands and the O atoms of the nitrate ligands. Hydrogen-bond details are provided in Table 2.

The intermolecular hydrogen bonds propagate in two dimensions, forming an infinite sheet-like motif that lies parallel to thebcplane (Fig. 2). Each of the N donor atoms forms hydrogen bonds to (at least) two O acceptor atoms, with only atoms O5 and O8 not involved in close interactions. The sheets stack along theaaxis, as shown in the crystal packing diagram (Fig. 3).

Experimental

The title compound was prepared fromcis-[Pd(en)Cl2] and identified as the desired product by comparison with literature data (Fujitaet al., 1996; Tercero-Morenoet al., 1996). Crystals of (I) suitable for the X-ray diffraction study were isolated from methanol after several days of slow evaporation. All reagents were purchased from Sigma– Aldrich.

Crystal data

C2H8N4O6Pd

Mr= 290.52

Monoclinic,P21=c

a= 16.8478 (6) A˚

b= 7.7746 (3) A˚

c= 13.0702 (5) A˚

= 109.816 (1)

V= 1610.62 (10) A˚3

Z= 8

Dx= 2.396 Mg m

3

MoKradiation

Cell parameters from 10524 reflections

= 2.4–28.3

= 2.32 mm1

T= 150 (2) K Block, colourless 0.510.300.16 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer

!scans

Absorption correction: multi-scan (SADABS; Sheldrick, 1999)

3881 independent reflections 3554 reflections withI> 2(I)

Rint= 0.019

max= 28.3

h=22!22 Figure 1

A representation of the asymmetric unit of (I), shown with 50% probability displacement ellipsoids.

Figure 2

Figure 3

Refinement

Refinement onF2 R[F2_{> 2(F}2_{)] = 0.016}

wR(F2) = 0.043

S= 1.03 3881 reflections 259 parameters

H atoms treated by a mixture of independent and constrained refinement

w= 1/[2

(Fo2) + (0.0236P)2 + 0.7251P]

whereP= (Fo2+ 2Fc2)/3 (/)max= 0.002

max= 1.08 e A˚ 3

min=0.40 e A˚ 3

Table 1

Selected geometric parameters (A˚ ,_).

N1—Pd1 2.0032 (14)

N2—Pd1 2.0231 (14)

N5—Pd2 2.0102 (15)

N6—Pd2 2.0150 (14)

O3—Pd1 2.0326 (12)

O4—Pd1 2.0492 (11)

O9—Pd2 2.0465 (12)

O12—Pd2 2.0426 (11)

N1—Pd1—N2 83.84 (6)

N1—Pd1—O3 172.80 (6)

N2—Pd1—O3 94.62 (5)

N1—Pd1—O4 90.81 (5)

N2—Pd1—O4 173.19 (5)

O3—Pd1—O4 90.16 (5)

N5—Pd2—N6 83.82 (6)

N5—Pd2—O12 95.14 (5)

N6—Pd2—O12 173.68 (5)

N5—Pd2—O9 173.01 (5)

N6—Pd2—O9 91.35 (5)

O12—Pd2—O9 89.11 (5)

Table 2

Hydrogen-bond geometry (A˚ ,_).

D—H A D—H H A D A D—H A

N2—H3 O7 0.90 (2) 2.23 (2) 2.9167 (19) 134 (2) N2—H3 O11i

0.90 (2) 2.45 (2) 3.0911 (19) 129 (2)

N2—H4 O1 0.89 (2) 2.49 (2) 3.009 (2) 118 (2)

N2—H4 O9ii

0.89 (2) 2.58 (2) 3.415 (2) 158 (2) N5—H6 O4 0.88 (2) 2.45 (2) 3.2837 (19) 160 (2) N5—H6 O4 0.88 (2) 2.45 (2) 3.2837 (19) 160 (2) N1—H2 O11ii

0.86 (2) 2.35 (2) 3.199 (2) 167 (2) N1—H2 O12ii

0.86 (2) 2.46 (2) 3.1177 (19) 133 (2) N1—H1 O9iii

0.88 (2) 2.24 (2) 3.0642 (18) 157 (2) N6—H7 O3 0.88 (2) 2.39 (2) 2.9550 (18) 122 (2) N6—H7 O10i

0.88 (2) 2.50 (2) 3.1324 (19) 130 (2)

N6—H7 O2 0.88 (2) 2.58 (2) 3.363 (2) 149 (2)

N6—H8 O4i 0.88 (2) 2.38 (2) 3.1695 (18) 150 (2) N6—H8 O6i

0.88 (2) 2.40 (2) 3.1628 (19) 145 (2)

Symmetry codes: (i)x;yþ3 2;z

1

2; (ii)x;y1;z; (iii)x;yþ 3 2;zþ

1 2.

C-bound H atoms were included in idealized positions and refined using a riding-model approximation, with methylene C—H bond lengths fixed at 0.99 A˚ . N-bound H atoms were located in a difference Fourier map and refined with bond-length restraints of 0.90 (2) A˚ . Uiso(H) values were fixed at 1.2Ueq(C) and 1.5Ueq(N). The maximum residual electron-density peak is located 0.86 A˚ from atom Pd2.

Data collection:SMART(Bruker, 1995); cell refinement:SAINT (Bruker, 1995); data reduction:SAINTandXPREP(Bruker, 1995); program(s) used to solve structure:SIR97 (Altomare et al., 1999); program(s) used to refine structure:SHELXL97(Sheldrick, 1997); molecular graphics: ORTEP3 (Farrugia, 1997) and WinGX32 (Farrugia, 1999); software used to prepare material for publication: enCIFer(Allenet al., 2004).

The authors gratefully acknowledge the Australian Research Council for financial support.

References

Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, M. (2004).J. Appl. Cryst.37, 335–338.

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999).J. Appl. Cryst.32, 115–119.

Bray, D. J., Liao, L.-L., Antonioli, B., Gloe, K., Lindoy, L. F., McMurtrie, J. C., Wei, G. & Zhang, X.-Y. (2005).Dalton Trans.pp. 2082–2083.

Bruker (1995).SMART(Version 5.054),SAINT(Version 6.45) andXPREP

(Version 6.02). Bruker AXS Inc., Madison, Wisconsin, USA.

Clegg, J. K., Lindoy, L. F., McMurtrie, J. C., Moubaraki, B. & Murray, K. (2004).Dalton Trans.pp. 2417–2423.

Clegg, J. K., Lindoy, L. F., McMurtrie, J. C. & Schilter, D. (2005).Dalton Trans.

pp. 857–864.

Farrugia, L. J. (1997).J. Appl. Cryst.30, 565. Farrugia, L. J. (1999).J. Appl. Cryst.32, 837–838.

Fujita, M., Aoyagi, M. & Ogura, K. (1996).Inorg. Chim. Acta,246, 53–57. Fujita, M., Tominaga, M., Hori, A. & Therrien, B. (2005).Acc. Chem. Res.38,

369–378.

Lindoy, L. F. & Atkinson, I. M. (2000).Self-Assembly in Supramolecular Systems. Monographs in Supramolecular Chemistry, Series Editor J. F. Stoddart. Cambridge: Royal Society of Chemistry.

Sheldrick, G. M. (1997).SHELXL97. University of Go¨ttingen, Germany. Sheldrick, G. M. (1999).SADABS. University of Go¨ttingen, Germany. Tercero-Moreno, A. M.-H. J. M., Gorza´lez-Garcia´, S. & Niclo´s-Gutie´rrez, J.

(1996).Inorg. Chim. Acta,253, 23–29.

metal-organic papers

m1942

supporting information

Acta Cryst. (2005). E₆₁, m1940–m1942 [doi:10.1107/S1600536805027224]

(Ethane-1,2-diamine)dinitratopalladium(II)

David J. Bray, Jack K. Clegg, Li-Ling Liao, Leonard F. Lindoy, John C. McMurtrie, David Schilter,

Gang Wei and Tae-Jin Won

S1. Comment

Our group has long been interested in the use of metal complexes as components for the construction of large

supramolecular architectures (Lindoy & Atkinson, 2000). In particular, we are interested in the construction and

chemistry of metallocyclic systems (Clegg et al., 2004, 2005). The title compound, (I), has found extensive use as a

precursor in the preparation of cyclic metallo-supramolecular structures (Fujita et al., 2005). Crystals suitable for this

study were obtained in the course of our investigation into the interactions of N-donor ligand systems (Bray et al., 2005)

with (I).

An ORTEP (Farrugia, 1997) representation of (I) is given in Fig. 1. As expected, each PdII _{ion has a geometry close to}

an ideal square-plane (Table 1). The N donor atoms of the bidentate ethane-1,2-diamine ligand (en) occupy two

coordination sites in a typical five-membered chelate arrangment. The remaining coordination sites are occupied by

nitrate O atoms of two nitrate ligands.

The asymmetric unit contains two of these complexes, which pack via intermolecular hydrogen bonds between the NH2

groups of the en ligands and the O atoms of the nitrate ligands. Hydrogen-bond details are provided in Table 2.

The intermolecular hydrogen bonds propagate in two dimensions, forming an infinite sheet-like motif that lies parallel

to the bc plane (Fig. 2). Each of the N donor atoms forms hydrogen bonds to (at least) two O acceptor atoms, with only

atoms O5 and O8 not involved in close interactions. The sheets stack along the a axis, as shown in the crystal packing

diagram (Fig. 3).

S2. Experimental

The title compound was prepared from cis-[Pd(en)Cl2] and identified as the desired product by comparison with literature

data (Fujita et al., 1996; Tercero-Moreno et al., 1996). Crystals of (I) suitable for the X-ray diffraction study were

isolated from methanol after several days of slow evaporation. All reagents were purchased from Sigma–Aldrich.

S3. Refinement

C-bound H atoms were included in idealized positions and refined using a riding-model approximation, with methylene C

—H bond lengths fixed at 0.99 Å. N-bound H atoms were located in the difference Fourier map and refined with

supporting information

sup-2

Acta Cryst. (2005). E61, m1940–m1942 Figure 1

Figure 2

A view of part of one of the two-dimensional sheets formed by hydrogen bonding. The sheets extend infinitely in the bc

supporting information

sup-4

Acta Cryst. (2005). E61, m1940–m1942 Figure 3

A view of (I), along the b axis. Alternate two-dimensional sheets are shown in red and green. There are no

hydrogen-bonding interactions connecting adjacent layers. Blue arrows indicate ?

(Ethane-1,2-diamine)dinitratopalladium(II)

Crystal data

C2H8N4O6Pd Mr = 290.52 Monoclinic, P21/c

Hall symbol: -P2ybc a = 16.8478 (6) Å b = 7.7746 (3) Å c = 13.0702 (5) Å β = 109.816 (1)°

V = 1610.62 (10) Å3 Z = 8

F(000) = 1136 Dx = 2.396 Mg m−3

Mo Kα radiation, λ = 0.71073 Å Cell parameters from 10524 reflections θ = 2.4–28.3°

T = 150 K Needle, colourless

0.51 × 0.30 × 0.16 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer

Radiation source: sealed tube Graphite monochromator ω scans

Absorption correction: multi-scan (SADABS; Sheldrick, 1999) Tmin = 0.514, Tmax = 0.690

15349 measured reflections 3881 independent reflections 3554 reflections with I > 2σ(I) Rint = 0.019

θmax = 28.3°, θmin = 3.1° h = −22→22

k = −10→10 l = −17→16

Refinement

Refinement on F2

Least-squares matrix: full R[F2 _{> 2σ(F}2_{)] = 0.016} wR(F2_{) = 0.043} S = 1.03 3881 reflections 259 parameters 8 restraints

Primary atom site location: structure-invariant direct methods

Secondary atom site location: difference Fourier map

Hydrogen site location: inferred from neighbouring sites

H atoms treated by a mixture of independent and constrained refinement

w = 1/[σ2_(F

o2) + (0.0236P)2 + 0.7251P]

where P = (Fo2 + 2Fc2)/3

(Δ/σ)max = 0.002

Δρmax = 1.08 e Å−3

Δρmin = −0.40 e Å−3

Special details

Experimental. The crystal was coated in Exxon Paratone N hydrocarbon oil and mounted on a thin mohair fibre attached

to a copper pin. Upon mounting on the diffractometer, the crystal was quenched to 150(K) under a cold nitrogen gas stream supplied by an Oxford Cryosystems Crystream and data were collected at this temperature. 234 standard

reflections were obtained by recollecting the first 50 CCD frames at the end of data collection. They were then used for a decay correction, giving an overall decay of 0.33%.

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 F}2_,

conventional R-factors R are based on F, with F set to zero for negative F2_{. The threshold expression of F}2 _{> σ(F}2_{) 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₎

x y z Uiso*/Ueq

supporting information

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Acta Cryst. (2005). E61, m1940–m1942

C4 0.42840 (10) 0.8026 (2) 0.23646 (14) 0.0201 (3) H7A 0.4702 0.8251 0.2000 0.024* H7B 0.4325 0.6800 0.2582 0.024* N1 0.16543 (9) 0.38548 (19) 0.39314 (12) 0.0183 (3) H1 0.1764 (13) 0.454 (3) 0.4501 (15) 0.027* H2 0.1697 (13) 0.280 (2) 0.4141 (17) 0.027* N2 0.13345 (9) 0.35657 (19) 0.17776 (12) 0.0196 (3) H3 0.1183 (14) 0.447 (2) 0.1329 (17) 0.029* H4 0.1420 (13) 0.265 (2) 0.1422 (17) 0.029* N3 0.31257 (9) 0.38063 (18) 0.13002 (12) 0.0193 (3) N4 0.40206 (9) 0.39355 (17) 0.47206 (12) 0.0189 (3) N5 0.37339 (10) 0.89330 (19) 0.37507 (12) 0.0194 (3) H5 0.3772 (13) 0.969 (3) 0.4257 (16) 0.029* H6 0.3761 (13) 0.791 (2) 0.4044 (17) 0.029* N6 0.34149 (9) 0.84238 (18) 0.16138 (11) 0.0180 (3) H7 0.3219 (12) 0.749 (2) 0.1230 (16) 0.027* H8 0.3493 (14) 0.919 (2) 0.1163 (17) 0.027* N7 0.10544 (9) 0.83412 (18) 0.08766 (11) 0.0199 (3) N8 0.18726 (9) 0.92392 (16) 0.41271 (12) 0.0186 (3) O1 0.28288 (8) 0.23489 (15) 0.12090 (11) 0.0277 (3) O2 0.34835 (9) 0.44032 (19) 0.06988 (11) 0.0310 (3) O3 0.30658 (8) 0.48244 (15) 0.20513 (10) 0.0236 (3) O4 0.33690 (7) 0.49827 (14) 0.43624 (9) 0.0197 (2) O5 0.40964 (8) 0.27554 (15) 0.41420 (11) 0.0260 (3) O6 0.45183 (8) 0.42377 (15) 0.56363 (11) 0.0270 (3) O7 0.10879 (8) 0.72811 (16) 0.15929 (11) 0.0274 (3) O8 0.04821 (8) 0.84143 (17) 0.00052 (11) 0.0300 (3) O9 0.16642 (7) 0.94747 (15) 0.10590 (10) 0.0196 (2) O10 0.21827 (8) 0.78038 (15) 0.43498 (11) 0.0268 (3) O11 0.14757 (8) 0.99788 (17) 0.46451 (10) 0.0286 (3) O12 0.19575 (7) 1.00942 (15) 0.33215 (9) 0.0209 (2) Pd1 0.239096 (8) 0.419159 (14) 0.302404 (10) 0.01465 (4) Pd2 0.266618 (7) 0.911995 (14) 0.246167 (10) 0.01437 (4)

Atomic displacement parameters (Å2₎

U11 _U22 _U33 _U12 _U13 _U23

N8 0.0196 (7) 0.0197 (7) 0.0163 (7) −0.0032 (5) 0.0059 (6) −0.0010 (5) O1 0.0347 (7) 0.0199 (6) 0.0305 (7) −0.0016 (5) 0.0137 (6) −0.0052 (5) O2 0.0287 (7) 0.0449 (8) 0.0258 (7) 0.0027 (6) 0.0174 (6) 0.0089 (6) O3 0.0315 (7) 0.0203 (6) 0.0252 (6) −0.0074 (5) 0.0177 (5) −0.0049 (5) O4 0.0174 (5) 0.0187 (5) 0.0206 (6) 0.0016 (4) 0.0033 (5) −0.0043 (4) O5 0.0310 (7) 0.0203 (6) 0.0286 (7) 0.0035 (5) 0.0125 (6) −0.0060 (5) O6 0.0240 (7) 0.0294 (7) 0.0223 (6) 0.0010 (5) 0.0008 (5) −0.0024 (5) O7 0.0306 (7) 0.0239 (6) 0.0277 (7) −0.0027 (5) 0.0097 (6) 0.0063 (5) O8 0.0239 (7) 0.0352 (7) 0.0239 (6) 0.0011 (5) −0.0011 (5) −0.0016 (6) O9 0.0180 (6) 0.0219 (5) 0.0183 (6) −0.0011 (5) 0.0055 (5) 0.0039 (5) O10 0.0335 (7) 0.0197 (6) 0.0281 (6) 0.0026 (5) 0.0116 (6) 0.0069 (5) O11 0.0320 (7) 0.0343 (7) 0.0263 (6) −0.0002 (6) 0.0186 (6) −0.0047 (6) O12 0.0272 (6) 0.0196 (6) 0.0196 (6) 0.0043 (5) 0.0129 (5) 0.0036 (5) Pd1 0.01615 (7) 0.01443 (7) 0.01398 (7) −0.00212 (4) 0.00591 (5) −0.00176 (4) Pd2 0.01580 (7) 0.01446 (7) 0.01336 (7) 0.00110 (4) 0.00559 (5) 0.00127 (4)

Geometric parameters (Å, º)

C1—N1 1.482 (2) N3—O2 1.2319 (19) C1—C2 1.505 (2) N3—O3 1.2914 (19) C1—H2A 0.9900 N4—O5 1.2230 (18) C1—H2B 0.9900 N4—O6 1.2289 (19) C2—N2 1.486 (2) N4—O4 1.3185 (17) C2—H3A 0.9900 N5—Pd2 2.0102 (15) C2—H3B 0.9900 N5—H5 0.873 (15) C3—N5 1.489 (2) N5—H6 0.875 (15) C3—C4 1.504 (2) N6—Pd2 2.0150 (14) C3—H6A 0.9900 N6—H7 0.880 (15) C3—H6B 0.9900 N6—H8 0.881 (15) C4—N6 1.493 (2) N7—O8 1.2189 (19) C4—H7A 0.9900 N7—O7 1.2341 (19) C4—H7B 0.9900 N7—O9 1.3126 (18) N1—Pd1 2.0032 (14) N8—O10 1.2248 (18) N1—H1 0.882 (15) N8—O11 1.2422 (19) N1—H2 0.863 (15) N8—O12 1.2935 (18) N2—Pd1 2.0231 (14) O3—Pd1 2.0326 (12) N2—H3 0.897 (15) O4—Pd1 2.0492 (11) N2—H4 0.886 (15) O9—Pd2 2.0465 (12) N3—O1 1.2279 (19) O12—Pd2 2.0426 (11)

supporting information

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Acta Cryst. (2005). E61, m1940–m1942

C1—C2—H3A 110.1 Pd2—N5—H6 109.3 (14) N2—C2—H3B 110.1 H5—N5—H6 108 (2) C1—C2—H3B 110.1 C4—N6—Pd2 110.58 (10) H3A—C2—H3B 108.4 C4—N6—H7 107.4 (14) N5—C3—C4 106.87 (13) Pd2—N6—H7 110.6 (14) N5—C3—H6A 110.3 C4—N6—H8 104.2 (14) C4—C3—H6A 110.3 Pd2—N6—H8 116.6 (14) N5—C3—H6B 110.3 H7—N6—H8 106.9 (19) C4—C3—H6B 110.3 O8—N7—O7 123.94 (15) H6A—C3—H6B 108.6 O8—N7—O9 117.45 (14) N6—C4—C3 107.43 (13) O7—N7—O9 118.61 (14) N6—C4—H7A 110.2 O10—N8—O11 123.87 (15) C3—C4—H7A 110.2 O10—N8—O12 120.38 (14) N6—C4—H7B 110.2 O11—N8—O12 115.74 (13) C3—C4—H7B 110.2 N3—O3—Pd1 122.12 (10) H7A—C4—H7B 108.5 N4—O4—Pd1 116.72 (9) C1—N1—Pd1 107.22 (11) N7—O9—Pd2 115.43 (9) C1—N1—H1 108.2 (14) N8—O12—Pd2 120.26 (10) Pd1—N1—H1 115.3 (14) N1—Pd1—N2 83.84 (6) C1—N1—H2 108.2 (14) N1—Pd1—O3 172.80 (6) Pd1—N1—H2 108.1 (14) N2—Pd1—O3 94.62 (5) H1—N1—H2 110 (2) N1—Pd1—O4 90.81 (5) C2—N2—Pd1 110.66 (10) N2—Pd1—O4 173.19 (5) C2—N2—H3 108.3 (14) O3—Pd1—O4 90.16 (5) Pd1—N2—H3 108.4 (14) N5—Pd2—N6 83.82 (6) C2—N2—H4 108.0 (14) N5—Pd2—O12 95.14 (5) Pd1—N2—H4 111.1 (14) N6—Pd2—O12 173.68 (5) H3—N2—H4 110 (2) N5—Pd2—O9 173.01 (5) O1—N3—O2 123.85 (15) N6—Pd2—O9 91.35 (5) O1—N3—O3 120.34 (14) O12—Pd2—O9 89.11 (5)

Hydrogen-bond geometry (Å, º)

D—H···A D—H H···A D···A D—H···A

N2—H3···O7 0.90 (2) 2.23 (2) 2.9167 (19) 134 (2) N2—H3···O11i _{0.90 (2) 2.45 (2) 3.0911 (19) 129 (2)}

N2—H4···O1 0.89 (2) 2.49 (2) 3.009 (2) 118 (2) N2—H4···O9ii _{0.89 (2) 2.58 (2) 3.415 (2) 158 (2)}

N5—H6···O4 0.88 (2) 2.45 (2) 3.2837 (19) 160 (2) N5—H6···O4 0.88 (2) 2.45 (2) 3.2837 (19) 160 (2) N1—H2···O11ii _{0.86 (2) 2.35 (2) 3.199 (2) 167 (2)}

N1—H2···O12ii _{0.86 (2) 2.46 (2) 3.1177 (19) 133 (2)}

N1—H1···O9iii _{0.88 (2) 2.24 (2) 3.0642 (18) 157 (2)}

N6—H7···O3 0.88 (2) 2.39 (2) 2.9550 (18) 122 (2) N6—H7···O10i _{0.88 (2) 2.50 (2) 3.1324 (19) 130 (2)}

N6—H7···O2 0.88 (2) 2.58 (2) 3.363 (2) 149 (2) N6—H8···O4i _{0.88 (2) 2.38 (2) 3.1695 (18) 150 (2)}

N6—H8···O6i _{0.88 (2) 2.40 (2) 3.1628 (19) 145 (2)}