Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Previous article
Next article
Previous article
Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Next article

metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 6| June 2010| Pages m638-m639
https://doi.org/10.1107/S1600536810016533

Di­chlorido(4,7-di­aza-1-azonia­cyclo­nonane-κ2N4,N7)palladium(II) p-toluene­sulfonate

Timothy A. Anthony,a Hadi D. Armana* and Judith A. Walmsleya*

aDepartment of Chemistry, The University of Texas at San Antonio, One UTSA Circle, San Antonio, Texas 78249-0698, USA
*Correspondence e-mail: hadi.arman@utsa.edu, judith.walmsley@utsa.edu

(Received 23 April 2010; accepted 5 May 2010; online 12 May 2010)

The title compound, [PdCl2(C6H16N3)](C7H7SO3), consists of a PdII atom bonded to two N atoms of the 1,4,7-triaza­cyclo­nonane (TACN) ligand and two chloride ions, which define a distorted square-planar geometry. The third N atom of the TACN ligand is protonated and hydrogen bonds to the p-toluene­sulfonate anion. The Cl—Pd—Cl angle is larger than the N—Pd—N angle. The packing is dominated by layers, which are formed by the criss-crossing of two different hydrogen-bonded chains. One chain is composed of hydrogen-bonded Pd(TACNH)Cl2+ cations, while the second is formed through hydrogen bonding between the p-toluene­sulfonate anion and the Pd(TACNH)Cl2+ cation.

Related literature

For background to complexes of PdII and PtII with 1,4,7-triaza­cyclo­nonane (TACN), see: McAuley & Whitcombe (1988[McAuley, A. & Whitcombe, T. W. (1988). Inorg. Chem. 27, 3090-3099.]); Blake et al. (1988[Blake, A. J., Gordon, L. M., Holder, A. J., Hyde, T. I., Reid, G. & Schröder, M. (1988). J. Chem. Soc. Chem. Commun. pp. 1452-1454..], 1993[Blake, A. J., Holder, A. J., Roberts, Y. V. & Schroder, M. (1993). J. Chem. Soc. Chem. Commun. pp. 260-262.]); Margulis & Zompa (1992[Margulis, T. N. & Zompa, L. J. (1992). Inorg. Chim. Acta, 201, 61-67.]); Hunter et al. (1988[Hunter, G., McAuley, A. & Whitcombe, T. W. (1988). Inorg. Chem. 27, 2634-2639.]); Davies et al. (2000[Davies, M. S., Fenton, R. R., Huq, F., Ling, E. C. H. & Hambley, T. W. (2000). Aust. J. Chem. 53, 451-456.]). For the synthesis of TACN, see: Kang & Jo (2003[Kang, J. & Jo, J. H. (2003). Bull. Korean Chem. Soc. 24, 1403-1406.]). For Pd—N and Pd—Cl bond distances in Pd(en)Cl2, see: Iball et al. (1975[Iball, J., MacDougall, M. & Scrimgeour, S. (1975). Acta Cryst. B31, 1672-1674.]).

[Scheme 1]

Experimental

Crystal data

  • [PdCl2(C6H16N3)](C7H7O3S)

  • Mr = 478.70

  • Triclinic, [P \overline 1]

  • a = 6.6663 (11) Å

  • b = 7.0023 (11) Å

  • c = 19.646 (3) Å

  • α = 92.149 (3)°

  • β = 92.301 (3)°

  • γ = 103.084 (4)°

  • V = 891.5 (2) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 1.47 mm−1

  • T = 98 K

  • 0.39 × 0.25 × 0.14 mm
Data collection

  • Rigaku AFC12 Kappa goniometer diffractometer

  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995[Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.839, Tmax = 1.000

  • 6224 measured reflections

  • 3998 independent reflections

  • 3941 reflections with I > 2σ(I)

  • Rint = 0.018
Refinement

  • R[F2 > 2σ(F2)] = 0.029

  • wR(F2) = 0.067

  • S = 1.00

  • 3998 reflections

  • 220 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.62 e Å−3

  • Δρmin = −0.98 e Å−3

Table 1
Selected geometric parameters (Å, °)

Pd1—N1 2.030 (2)
Pd1—N2 2.060 (2)
Pd1—Cl1 2.3053 (8)
Pd1—Cl2 2.3115 (7)
N1—Pd1—N2 82.71 (9)
Cl1—Pd1—Cl2 94.02 (3)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1a⋯O1i 0.82 (6) 2.05 (6) 2.833 (3) 159 (6)
N2—H2a⋯Cl1ii 0.79 (5) 2.66 (6) 3.365 (2) 149 (5)
N3—H3a⋯O2 0.75 (6) 2.04 (6) 2.743 (3) 156 (6)
N3—H3d⋯Cl2iii 0.84 (5) 2.31 (6) 3.136 (3) 171 (5)
Symmetry codes: (i) x+1, y+1, z; (ii) x-1, y, z; (iii) x, y-1, z.

Data collection: CrystalClear (Rigaku/MSC, 2005[Rigaku/MSC (2005). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEPII (Johnson, 1976[Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43. Submitted.]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810016533/tk2666sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810016533/tk2666Isup2.hkl

checkCIF report


Comment top

Complexes of PdII and PtII with 1,4,7,-triazacyclononane (TACN) have been reported in which the metal ion is coordinated to all three of the TACN nitrogen atoms (McAuley & Whitcombe, 1988) or to only two of the N atoms (Blake et al., 1988; Blake et al., 1993; Margulis & Zompa, 1992; Hunter et al., 1988). In the latter case, under acidic conditions, the non-Pd bonded N atom becomes protonated. As a result, hydrogen bonding networks can be formed in the presence of an acceptor site. A similar type of complex has been reported for PtII (Davies et al., 2000).

The title salt is comprised of a protonated Pd(TACNH)Cl2+ cation and a p-toluenesulfonate ion, Fig. 1. The Pd—N and Pd—Cl bond distances, Table 1, are similar to the bond distances observed in Pd(en)Cl2 of 1.9798 (7) and 2.3084 (8) Å for Pd—N and Pd—Cl bonds, respectively (Iball et al., 1975). The geometry about the PdIIatom is essentially square planar, but with the Cl1—Pd—Cl2 bond angle larger than the N1—Pd—N2 bond angle., Table 1 The dimer associates into a supramolecular chain via a nine member, ···O1—S1—O2···H3a—N3—C—C—N1—H1a···, synthon, Fig 2. A second hydrogen bonded chain is observed that is formed between protonated Pd(TACNH)Cl2+ cations. These chains are composed of a seven member, ···Cl2—Pd—N1—C—C—N3—H3d···, repeat unit involving the protonated N atom, Fig 3. Hydrogen bonding distances are given in Table 1. These two hydrogen bonded chains are situated approximately perpendicular to one another which allows for the formation of 2-D hydrogen bonded layers, Fig 4.

Related literature top

For background to complexes of PdII and PtII with 1,4,7,-triazacyclononane (TACN), see: McAuley & Whitcombe (1988); Blake et al. (1988, 1993); Margulis & Zompa (1992); Hunter et al. (1988); Davies et al. (2000). For the synthesis of TACN, see: Kang & Jo (2003). For Pd—N and Pd—Cl bond distances in Pd(en)Cl2, see: Iball et al. (1975).

Experimental top

The ligand (TACN) was prepared according to the procedure reported in the literature (Kang & Jo, 2003). K2PdCl4 (0.126 g, 0.387 mmol) was dissolved in deionized H2O (20 ml) and heated to 343 K. TACN (0.0500 g, 0.387 mmol) was dissolved in 50% 2-propanol/50% water solution (20 ml) and heated to 343 K. The two hot solutions were combined, removed from the heat and allowed to stir for 48 h. Yellow-brown crystals precipitated and were isolated by suction filtration. These were recrystallized from a 50% 2-propanol/50% water mixture to obtain crystals suitable for X-ray analysis.

Refinement top

Carbon-bound H-atoms were placed in calculated positions(C—H 0.93 - 0.97 Å) and were included in the refinement in the riding model approximation with Uiso(H) set to 1.2-1.5 Ueq(C). The nitrogen-bound H-atoms were located in a difference Fourier map and were refined with Uiso(H) = 1.2Ueq(N).

Structure description top

Complexes of PdII and PtII with 1,4,7,-triazacyclononane (TACN) have been reported in which the metal ion is coordinated to all three of the TACN nitrogen atoms (McAuley & Whitcombe, 1988) or to only two of the N atoms (Blake et al., 1988; Blake et al., 1993; Margulis & Zompa, 1992; Hunter et al., 1988). In the latter case, under acidic conditions, the non-Pd bonded N atom becomes protonated. As a result, hydrogen bonding networks can be formed in the presence of an acceptor site. A similar type of complex has been reported for PtII (Davies et al., 2000).

The title salt is comprised of a protonated Pd(TACNH)Cl2+ cation and a p-toluenesulfonate ion, Fig. 1. The Pd—N and Pd—Cl bond distances, Table 1, are similar to the bond distances observed in Pd(en)Cl2 of 1.9798 (7) and 2.3084 (8) Å for Pd—N and Pd—Cl bonds, respectively (Iball et al., 1975). The geometry about the PdIIatom is essentially square planar, but with the Cl1—Pd—Cl2 bond angle larger than the N1—Pd—N2 bond angle., Table 1 The dimer associates into a supramolecular chain via a nine member, ···O1—S1—O2···H3a—N3—C—C—N1—H1a···, synthon, Fig 2. A second hydrogen bonded chain is observed that is formed between protonated Pd(TACNH)Cl2+ cations. These chains are composed of a seven member, ···Cl2—Pd—N1—C—C—N3—H3d···, repeat unit involving the protonated N atom, Fig 3. Hydrogen bonding distances are given in Table 1. These two hydrogen bonded chains are situated approximately perpendicular to one another which allows for the formation of 2-D hydrogen bonded layers, Fig 4.

For background to complexes of PdII and PtII with 1,4,7,-triazacyclononane (TACN), see: McAuley & Whitcombe (1988); Blake et al. (1988, 1993); Margulis & Zompa (1992); Hunter et al. (1988); Davies et al. (2000). For the synthesis of TACN, see: Kang & Jo (2003). For Pd—N and Pd—Cl bond distances in Pd(en)Cl2, see: Iball et al. (1975).

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot (50% probability) of the asymmetric unit of the title salt. Carbon bound hydrogen atoms are removed for clarity.
[Figure 2] Fig. 2. Hydrogen bonded chain formed between the protonated Pd(TACNH)Cl2+ cation and the p-toluenesulfonate anion; non-participating hydrogen atoms have been removed for clarity. Thermal ellipsoids are shown at 50% probability.
[Figure 3] Fig. 3. Hydrogen bonded chain formed between protonated Pd(TACNH)Cl2+ ions; non- participating hydrogen atoms have been removed for clarity. Thermal ellipsoids are shown at 50% probability.
[Figure 4] Fig. 4. Illustration of the hydrogen bonded layer (view down the c axis); non-participating hydrogen atoms have been removed for clarity. Thermal ellipsoids are shown at 50% probability.
Dichlorido(4,7-diaza-1-azoniacyclononane- κ2N4,N7)palladium(II) p-toluenesulfonate top
Crystal data top
[PdCl2(C6H16N3)](C7H7O3S)Z = 2
Mr = 478.70F(000) = 484
Triclinic, P1Dx = 1.783 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.6663 (11) ÅCell parameters from 4441 reflections
b = 7.0023 (11) Åθ = 3.0–40.2°
c = 19.646 (3) ŵ = 1.47 mm−1
α = 92.149 (3)°T = 98 K
β = 92.301 (3)°Prism, orange
γ = 103.084 (4)°0.39 × 0.25 × 0.14 mm
V = 891.5 (2) Å3
Data collection top
Rigaku AFC12 Kappa goniometer
diffractometer		3998 independent reflections
Radiation source: sealed tube3941 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.018
Detector resolution: 14.286 pixels mm-1θmax = 27.5°, θmin = 3.0°
ω scansh = −8→8
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		k = −9→8
Tmin = 0.839, Tmax = 1.000l = −25→24
6224 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.029Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.067H atoms treated by a mixture of independent and constrained refinement
S = 1.00 w = 1/[σ2(Fo2) + (0.007P)2 + 4.1P]
where P = (Fo2 + 2Fc2)/3
3998 reflections(Δ/σ)max = 0.001
220 parametersΔρmax = 0.62 e Å−3
0 restraintsΔρmin = −0.98 e Å−3
Crystal data top
[PdCl2(C6H16N3)](C7H7O3S)γ = 103.084 (4)°
Mr = 478.70V = 891.5 (2) Å3
Triclinic, P1Z = 2
a = 6.6663 (11) ÅMo Kα radiation
b = 7.0023 (11) ŵ = 1.47 mm−1
c = 19.646 (3) ÅT = 98 K
α = 92.149 (3)°0.39 × 0.25 × 0.14 mm
β = 92.301 (3)°
Data collection top
Rigaku AFC12 Kappa goniometer
diffractometer		3998 independent reflections
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		3941 reflections with I > 2σ(I)
Tmin = 0.839, Tmax = 1.000Rint = 0.018
6224 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0290 restraints
wR(F2) = 0.067H atoms treated by a mixture of independent and constrained refinement
S = 1.00Δρmax = 0.62 e Å−3
3998 reflectionsΔρmin = −0.98 e Å−3
220 parameters
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
xyzUiso*/Ueq
Pd10.97009 (3)1.13904 (3)0.126918 (10)0.00972 (6)
Cl20.84514 (10)1.25666 (9)0.02940 (3)0.01338 (13)
Cl11.31092 (10)1.25684 (10)0.10367 (3)0.01477 (13)
N11.0477 (4)1.0307 (3)0.21612 (12)0.0107 (4)
N20.6749 (3)1.0232 (3)0.15540 (12)0.0119 (4)
N30.8065 (4)0.6217 (4)0.12108 (13)0.0131 (5)
C51.0277 (4)0.7097 (4)0.14512 (15)0.0135 (5)
H5A1.09020.79780.11100.016*
H5B1.10000.60420.14650.016*
C40.6940 (4)0.7353 (4)0.07501 (14)0.0133 (5)
H4A0.60680.64280.04220.016*
H4B0.79540.82250.04970.016*
C61.0657 (4)0.8215 (4)0.21375 (14)0.0125 (5)
H6A0.96930.75110.24490.015*
H6B1.20320.81870.23110.015*
C30.5617 (4)0.8563 (4)0.10909 (15)0.0139 (5)
H3B0.48580.90820.07390.017*
H3C0.46160.77000.13520.017*
C20.6799 (4)0.9703 (4)0.22882 (14)0.0150 (5)
H2B0.65670.82900.23150.018*
H2C0.57151.01370.25220.018*
C10.8864 (4)1.0674 (4)0.26239 (14)0.0143 (5)
H1B0.89751.20730.26940.017*
H1C0.90361.01280.30630.017*
S10.48600 (10)0.43932 (10)0.28213 (3)0.01295 (14)
O10.3964 (3)0.2362 (3)0.29720 (10)0.0153 (4)
O20.6622 (3)0.4531 (3)0.23865 (10)0.0162 (4)
O30.3348 (4)0.5425 (3)0.25768 (12)0.0240 (5)
C70.5938 (5)0.5596 (4)0.36084 (15)0.0168 (6)
C80.7933 (5)0.5552 (5)0.38198 (17)0.0244 (7)
H8A0.87250.49370.35450.029*
C90.8743 (6)0.6442 (5)0.44501 (18)0.0316 (8)
H9A1.00870.64220.45900.038*
C120.4771 (6)0.6539 (5)0.40103 (18)0.0286 (7)
H12A0.34470.66020.38610.034*
C110.5605 (6)0.7399 (6)0.4645 (2)0.0373 (9)
H11A0.48110.80140.49190.045*
C100.7584 (6)0.7355 (5)0.48716 (17)0.0329 (9)
C130.8478 (8)0.8282 (7)0.55589 (19)0.0492 (13)
H13A0.74740.88420.57810.074*
H13B0.96860.92930.54960.074*
H13C0.88420.72990.58360.074*
H1A1.158 (8)1.102 (8)0.230 (3)0.059*
H2A0.624 (8)1.114 (8)0.151 (3)0.059*
H3A0.742 (8)0.592 (8)0.151 (3)0.059*
H3D0.809 (8)0.516 (8)0.100 (3)0.059*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Pd10.00972 (10)0.00856 (10)0.01090 (11)0.00177 (7)0.00143 (7)0.00151 (7)
Cl20.0159 (3)0.0127 (3)0.0122 (3)0.0043 (2)0.0012 (2)0.0019 (2)
Cl10.0111 (3)0.0167 (3)0.0161 (3)0.0015 (2)0.0024 (2)0.0038 (2)
N10.0111 (11)0.0110 (11)0.0091 (11)0.0001 (8)0.0017 (8)0.0009 (8)
N20.0092 (10)0.0109 (11)0.0162 (12)0.0035 (8)0.0025 (8)0.0011 (9)
N30.0149 (11)0.0112 (11)0.0130 (12)0.0024 (9)0.0021 (9)0.0012 (9)
C50.0099 (12)0.0132 (13)0.0180 (14)0.0033 (10)0.0018 (10)0.0020 (10)
C40.0147 (13)0.0126 (12)0.0118 (13)0.0019 (10)−0.0008 (10)0.0000 (10)
C60.0120 (12)0.0114 (12)0.0145 (13)0.0032 (10)0.0009 (10)0.0030 (10)
C30.0103 (12)0.0135 (13)0.0171 (14)0.0009 (10)0.0007 (10)0.0006 (10)
C20.0159 (13)0.0154 (13)0.0140 (13)0.0032 (11)0.0049 (10)0.0028 (10)
C10.0167 (13)0.0149 (13)0.0117 (13)0.0043 (11)0.0049 (10)−0.0007 (10)
S10.0134 (3)0.0117 (3)0.0133 (3)0.0020 (2)0.0007 (2)0.0011 (2)
O10.0175 (10)0.0135 (9)0.0128 (10)−0.0013 (8)0.0019 (8)0.0007 (7)
O20.0141 (10)0.0204 (10)0.0132 (10)0.0018 (8)0.0024 (7)0.0027 (8)
O30.0238 (11)0.0224 (11)0.0288 (12)0.0118 (9)−0.0025 (9)0.0027 (9)
C70.0227 (15)0.0121 (13)0.0132 (13)−0.0012 (11)0.0032 (11)0.0002 (10)
C80.0283 (17)0.0235 (16)0.0201 (16)0.0042 (13)−0.0022 (13)−0.0014 (12)
C90.0343 (19)0.0331 (19)0.0211 (17)−0.0046 (15)−0.0055 (14)0.0012 (14)
C120.0277 (17)0.0256 (17)0.0291 (18)−0.0008 (14)0.0098 (14)−0.0090 (14)
C110.046 (2)0.0320 (19)0.0274 (19)−0.0054 (17)0.0191 (17)−0.0105 (15)
C100.047 (2)0.0265 (17)0.0144 (16)−0.0148 (15)0.0065 (14)−0.0030 (13)
C130.068 (3)0.044 (2)0.0176 (18)−0.024 (2)0.0062 (18)−0.0074 (16)
Geometric parameters (Å, º) top
Pd1—N12.030 (2)C2—C11.504 (4)
Pd1—N22.060 (2)C2—H2B0.9700
Pd1—Cl12.3053 (8)C2—H2C0.9700
Pd1—Cl22.3115 (7)C1—H1B0.9700
N1—C11.495 (3)C1—H1C0.9700
N1—C61.495 (3)S1—O31.444 (2)
N1—H1A0.82 (5)S1—O11.459 (2)
N2—C31.493 (3)S1—O21.468 (2)
N2—C21.504 (4)S1—C71.777 (3)
N2—H2A0.79 (5)C7—C121.381 (4)
N3—C41.511 (4)C7—C81.385 (5)
N3—C51.512 (4)C8—C91.396 (5)
N3—H3A0.76 (6)C8—H8A0.9300
N3—H3D0.83 (6)C9—C101.388 (6)
C5—C61.516 (4)C9—H9A0.9300
C5—H5A0.9700C12—C111.400 (5)
C5—H5B0.9700C12—H12A0.9300
C4—C31.512 (4)C11—C101.383 (6)
C4—H4A0.9700C11—H11A0.9300
C4—H4B0.9700C10—C131.515 (5)
C6—H6A0.9700C13—H13A0.9600
C6—H6B0.9700C13—H13B0.9600
C3—H3B0.9700C13—H13C0.9600
C3—H3C0.9700
N1—Pd1—N282.71 (9)N2—C3—H3C108.4
N1—Pd1—Cl192.14 (7)C4—C3—H3C108.4
N2—Pd1—Cl1174.84 (7)H3B—C3—H3C107.4
N1—Pd1—Cl2173.69 (7)N2—C2—C1109.3 (2)
N2—Pd1—Cl291.14 (7)N2—C2—H2B109.8
Cl1—Pd1—Cl294.02 (3)C1—C2—H2B109.8
C1—N1—C6112.8 (2)N2—C2—H2C109.8
C1—N1—Pd1103.19 (17)C1—C2—H2C109.8
C6—N1—Pd1116.87 (17)H2B—C2—H2C108.3
C1—N1—H1A108 (4)N1—C1—C2107.4 (2)
C6—N1—H1A109 (4)N1—C1—H1B110.2
Pd1—N1—H1A106 (4)C2—C1—H1B110.2
C3—N2—C2112.6 (2)N1—C1—H1C110.2
C3—N2—Pd1113.10 (17)C2—C1—H1C110.2
C2—N2—Pd1109.76 (17)H1B—C1—H1C108.5
C3—N2—H2A109 (4)O3—S1—O1113.12 (13)
C2—N2—H2A110 (4)O3—S1—O2113.98 (13)
Pd1—N2—H2A101 (4)O1—S1—O2111.41 (12)
C4—N3—C5119.6 (2)O3—S1—C7106.63 (14)
C4—N3—H3A108 (4)O1—S1—C7106.18 (13)
C5—N3—H3A110 (4)O2—S1—C7104.72 (13)
C4—N3—H3D107 (4)C12—C7—C8120.5 (3)
C5—N3—H3D105 (4)C12—C7—S1119.9 (3)
H3A—N3—H3D105 (5)C8—C7—S1119.7 (2)
N3—C5—C6117.7 (2)C7—C8—C9119.3 (3)
N3—C5—H5A107.9C7—C8—H8A120.3
C6—C5—H5A107.9C9—C8—H8A120.3
N3—C5—H5B107.9C10—C9—C8121.4 (4)
C6—C5—H5B107.9C10—C9—H9A119.3
H5A—C5—H5B107.2C8—C9—H9A119.3
N3—C4—C3116.7 (2)C7—C12—C11119.3 (4)
N3—C4—H4A108.1C7—C12—H12A120.4
C3—C4—H4A108.1C11—C12—H12A120.4
N3—C4—H4B108.1C10—C11—C12121.4 (3)
C3—C4—H4B108.1C10—C11—H11A119.3
H4A—C4—H4B107.3C12—C11—H11A119.3
N1—C6—C5117.5 (2)C11—C10—C9118.1 (3)
N1—C6—H6A107.9C11—C10—C13121.3 (4)
C5—C6—H6A107.9C9—C10—C13120.6 (4)
N1—C6—H6B107.9C10—C13—H13A109.5
C5—C6—H6B107.9C10—C13—H13B109.5
H6A—C6—H6B107.2H13A—C13—H13B109.5
N2—C3—C4115.6 (2)C10—C13—H13C109.5
N2—C3—H3B108.4H13A—C13—H13C109.5
C4—C3—H3B108.4H13B—C13—H13C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1a···O1i0.82 (6)2.05 (6)2.833 (3)159 (6)
N2—H2a···Cl1ii0.79 (5)2.66 (6)3.365 (2)149 (5)
N3—H3a···O20.75 (6)2.04 (6)2.743 (3)156 (6)
N3—H3d···Cl2iii0.84 (5)2.31 (6)3.136 (3)171 (5)
Symmetry codes: (i) x+1, y+1, z; (ii) x−1, y, z; (iii) x, y−1, z.

Experimental details

Crystal data
Chemical formula[PdCl2(C6H16N3)](C7H7O3S)
Mr478.70
Crystal system, space groupTriclinic, P1
Temperature (K)98
a, b, c (Å)6.6663 (11), 7.0023 (11), 19.646 (3)
α, β, γ (°)92.149 (3), 92.301 (3), 103.084 (4)
V (Å3)891.5 (2)
Z2
Radiation typeMo Kα
µ (mm−1)1.47
Crystal size (mm)0.39 × 0.25 × 0.14
Data collection
DiffractometerRigaku AFC12 Kappa goniometer
Absorption correctionMulti-scan
(ABSCOR; Higashi, 1995)
Tmin, Tmax0.839, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections		6224, 3998, 3941
Rint0.018
(sin θ/λ)max (Å−1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.029, 0.067, 1.00
No. of reflections3998
No. of parameters220
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.62, −0.98

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPII (Johnson, 1976), publCIF (Westrip, 2010).

Selected geometric parameters (Å, º) top
Pd1—N12.030 (2)Pd1—Cl12.3053 (8)
Pd1—N22.060 (2)Pd1—Cl22.3115 (7)
N1—Pd1—N282.71 (9)Cl1—Pd1—Cl294.02 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1a···O1i0.82 (6)2.05 (6)2.833 (3)159 (6)
N2—H2a···Cl1ii0.79 (5)2.66 (6)3.365 (2)149 (5)
N3—H3a···O20.75 (6)2.04 (6)2.743 (3)156 (6)
N3—H3d···Cl2iii0.84 (5)2.31 (6)3.136 (3)171 (5)
Symmetry codes: (i) x+1, y+1, z; (ii) x−1, y, z; (iii) x, y−1, z.
Bond distances and angles for hydrogen-bonding interactions (Å, °) top
D···OX—D···AS=O···D
C1,C6—N1···O1i2.833 (3)97.42 (16), 104.83 (15)
N1—H1a···O1i2.05 (5)159 (5)
C4,C5—N3···O22.743 (3)125.55 (18), 99.40 (17)
N3—H3a···O22.04 (6)156 (6)
N3—H3d···Cl2ii2.31 (6)171 (5)
C4,C5—N3···Cl2ii3.136 (3)104.10 (16), 102.66 (16)
Pd—Cl2—H3diii85 (1)
Pd—Cl2—N3iii86.58 (5)
S1—O1···N1iv118.00 (12)
S1—O1···H1aiv113.3 (15)
S1—O2···N3139.70 (12)
S1—O2···H3a133.4 (16)
Symmetry codes: (i) 1+x, 1+y, z; (ii) x, -1+y, z; (iii) x, 1+y, z; (iv) -1+x, -1+y, z.
 

Acknowledgements

Support from the Department of Chemistry at The University of Texas is gratefully acknowledged.

References

First citationBlake, A. J., Gordon, L. M., Holder, A. J., Hyde, T. I., Reid, G. & Schröder, M. (1988). J. Chem. Soc. Chem. Commun. pp. 1452–1454..  CrossRef Web of Science Google Scholar
 First citationBlake, A. J., Holder, A. J., Roberts, Y. V. & Schroder, M. (1993). J. Chem. Soc. Chem. Commun. pp. 260–262.  CrossRef Web of Science Google Scholar
 First citationDavies, M. S., Fenton, R. R., Huq, F., Ling, E. C. H. & Hambley, T. W. (2000). Aust. J. Chem. 53, 451–456.  Web of Science CSD CrossRef CAS Google Scholar
 First citationHigashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.  Google Scholar
 First citationHunter, G., McAuley, A. & Whitcombe, T. W. (1988). Inorg. Chem. 27, 2634–2639.  CSD CrossRef CAS Web of Science Google Scholar
 First citationIball, J., MacDougall, M. & Scrimgeour, S. (1975). Acta Cryst. B31, 1672–1674.  CSD CrossRef CAS IUCr Journals Web of Science Google Scholar
 First citationJohnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA.  Google Scholar
 First citationKang, J. & Jo, J. H. (2003). Bull. Korean Chem. Soc. 24, 1403–1406.  CAS Google Scholar
 First citationMargulis, T. N. & Zompa, L. J. (1992). Inorg. Chim. Acta, 201, 61–67.  CSD CrossRef CAS Web of Science Google Scholar
 First citationMcAuley, A. & Whitcombe, T. W. (1988). Inorg. Chem. 27, 3090–3099.  CrossRef CAS Web of Science Google Scholar
 First citationRigaku/MSC (2005). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationWestrip, S. P. (2010). J. Appl. Cryst. 43. Submitted.  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.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 6| June 2010| Pages m638-m639
https://doi.org/10.1107/S1600536810016533
Follow Acta Cryst. E
Sign up for e-alerts
E-alerts
Follow Acta Cryst. on Twitter
Twitter
Follow us on facebook
Facebook
Sign up for RSS feeds
RSS