Syntheses, characterization and x-ray structures of the first copper(I) and silver(I) complexes with ATT (ATT = 6-Aza-2-thiothymine)

Article abstract of DOI:10.1002/zaac.200300362

The reaction of copper(I) chloride with 6-aza-2-thiothymine (ATT, 1) and triphenylphosphane in methanol/chloroform gives [(ATT)CuCl(PPh₃)] (2) as a neutral complex. [(ATT)Ag(NO₃)-(PPh₃) ₂]·MeOH (3) can be obtained by the reaction of 1 with silver(I) nitrate and triphenylphosphane in methanol/chloroform in excellent yields and the single crystals of 3 can be obtained from acetonitril solution. Both complexes were characterized by infrared spectroscopy, elemental analyses as well as by X-ray diffraction studies. Crystal data for 2 at -80°C: space group 12/a with a = 1859.3(1), b = 1143.2(1), c = 2208.2(1) pm, β = 104.84(1)°, Z = 8, R₁ = 0.0355 and for 3 at -80°C: space group P2₁/c with a = 1344.1(1), b = 1553.6(1), c = 1977,3(3) pm, β = 105.26(1)°, Z = 4, R₁ = 0.0436.

Full text of DOI:10.1002/zaac.200300362

Syntheses, Characterization and X-Ray Structures of the first Copper(I) and
Silver(I) Complexes with ATT (ATT ؍ 6-Aza-2-thiothymine)
Mitra Ghassemzadeh*,a, Mostafa Mohammad Pooraminib, Maasoomeh Tabatabaeec, and Majid M. Heravid
Tehran/Iran, a Chemistry Chemical Engineering Research Center of Iran, b Islamic Azad University, Science and Research Campus,
c Shahid Beheshty University, d Azzahra University, School of Sciences
Bernhard Neumüller
Marburg, Fachbereich Chemie der Universität
Received November 11th, 2003.
Abstract. The reaction of copper(I) chloride with 6-aza-2-thiothym-
ine (ATT, 1) and triphenylphosphane in methanol/chloroform gives
[(ATT)CuCl(PPh3)] (2) as a neutral complex. [(ATT)Ag(NO3)-
(PPh3)2]·MeOH (3) can be obtained by the reaction of 1 with
silver(I) nitrate and triphenylphosphane in methanol/chloroform in
excellent yields and the single crystals of 3 can be obtained from
acetonitril solution.
data for 2 at Ϫ80°C: space group I2/a with a ϭ 1859.3(1), b ϭ
1143.2(1), c ϭ 2208.2(1) pm, β ϭ 104.84(1)°, Z ϭ 8, R1 ϭ 0.0355
and for 3 at Ϫ80°C: space group P21/c with a ϭ 1344.1(1), b ϭ
1553.6(1), c ϭ 1977,3(3) pm, β ϭ 105.26(1)°, Z ϭ 4, R1 ϭ 0.0436.
Keywords: Copper; Silver; Thiothymine complexes; Crystal struc-
Both complexes were characterized by infrared spectroscopy,
elemental analyses as well as by X-ray diffraction studies. Crystal
tures
Synthesen und Bestimmung der ersten Kupfer(I)- and Silber(I)-Komplexe mit ATT
(ATT ؍ 6-Aza-2-thiothymin)
Inhaltsübersicht. Die Reaktion von Kupfer(I)chlorid mit 6-Aza-2-
thiothymin (ATT, 1) und Triphenylphosphan in Methanol/Chloro-
form ergibt den Neutralkomplex [(ATT)CuCl(PPh3)] (2).
[(ATT)Ag(NO3)(PPh3)2]·MeOH (3) kann in sehr guter Ausbeute
erhalten werden, wenn Silber(I)nitrat mit ATT und Triphenylphos-
phan in Methanol/Chloroform umgesetzt wird. Geeignete Einkris-
talle für die Röntgenstrukturanalyse wurden aus der Acetonitril-
Lösung von 3 erhalten. Die Komplexe wurden mittels IR-Spektro-
skopie, Elementaranalysen und Röntgenstrukturanalysen charakte-
risiert. Kristalldaten für 2 bei Ϫ80°C: Raumgruppe I2/a mit a ϭ
1859,3(1), b ϭ 1143,2(1), c ϭ 2208,2(1) pm, β ϭ 104,84(1)°, Z ϭ
8, R1 ϭ 0,0355 und für 3 at Ϫ 80°C: Raumgruppe P21/c mit a ϭ
1344,1(1), b ϭ 1553,6(1), c ϭ 1977,3(3) pm, β ϭ 105,26(1)°, Z ϭ
4, R1 ϭ 0,0436.
1 Introduction
gous CuI and CuII ions and found that the AMTTO reacts
with CuI as a monodetate in ratio 2:1, while it reacts with
CuII as a bidentate one in a ratio of 1:1. In the latter com-
plex the ligand occupied two equatorial positions in the
Jahn-Teller distorted stretched octahedron [4c]. We have
studied also the behavior of the synthesized complexes
against the nucleophile PPh3. As part of our continuing
interest in the syntheses and characterization of heterocyclic
thione complexes of transition metals, specially silver(I), we
reported on further thione argentanacycles [5].
There is considerable interest in the coordination chemistry
of chelating ligands containing mixed functionalities [1].
Our group has previously synthesized and characterized the
AMTTO-complexes of PdII-, PtII-, AgI-, CuI- and CuII-ions
(AMTTO ϭ 4-amino-6-methyl-1,2,4-triazin-thione-5-one).
In our investigations in the coordination chemistry of hy-
drazine family, we have shown that the AMTTO reacts with
palladium(II) halides such as chloride, bromide and iodide
as a S,N-chelating ligand [2] and with silver(I) nitrate ac-
cording to the “Pearson Principles” [3] as a unidentate one
via its sulfur atom with a weak Ag···N interaction, which
leads to a 2ϩ2 coordination on the silver atom [4]. We have
also studied the behavior of the AMTTO to the homolo-
In this communication we wish to report the synthesis,
characterization and crystal structure of copper(I) and
silver(I) complexes containing another representative of
hydrazine family, namely ATT.
2 Syntheses and Characterization of 2 and 3
* Dr. M. Ghassemzadeh
Chemistry and Chemical Engineering Research Center of Iran
P.O. Box 14335-186
Tehran/Iran
2 can be prepared by the reaction of CuCl, PPh3 and 1 in
a molar ratio 1:1:1 in methanol/chloroform according to
equation (1).
Z. Anorg. Allg. Chem. 2004, 630, 403Ϫ406
DOI: 10.1002/zaac.200300362
 2004 WILEY-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim
403

M. Ghassemzadeh, M. M. Pooramini, M. Tabatabaee, M. M. Heravi
MeOH/CHCl3
coordinated CuI, which caused a reduction of the other two
selected angles at the metal site with 114.86(3)°
(P1ϪCu1ϪS1) and 117.62(3)° (S1ϪCu1ϪCl1).
1 ϩ CuCl ϩ PPh3
Ǟ [(ATT)CuCl(PPh3)]
(1)
2
The CuϪP bond distance with 220.42(6) pm is shorter
than those observed in [(Ph3P)2CuCl]·0.5THF (average
226.2 pm) [7] and [(Ph3P)2CuCl]·0.5C6H6 [average 226.6
pm] [10] and is slightly longer than those observed in the
binuclear CuI complex [(Ph3P)2CuCl2Cu(PPh3)] containing
three and four coordinated copper moieties. (CuϪP: C.N.
3: 218.1(1) pm) and is shorter than those in four coordi-
nated copper in the same complex (average 223.55 pm) [7].
Similar CuϪCl distances, here 223.32(6) pm, have been
observed in complexes with three coordinated CuI such as
[(Ph3P)2CuCl]·0.5THF (221.4(1) pm) and [(Ph3P)2CuCl2Cu-
(PPh3)] (225.0(1) pm) [7] and it is slightly shorter than the
distances observed in the complexes with four coordinated
copper complexes like [Cu(AMTTO)2(PPh3)2Cl] (236.7(2)
pm) and [(C4H4N3SON(ϭCMe2)Cu(PPh3)2Cl] (238.0(1)
pm) [4b, 4c].
The CuϪS bond distance of 226.50(6) pm is consistent
with the distances usually found for trigonally coordinated
copper(I) ions containing S-donor ligands.
The complexes in 2 are connected by strong hydrogen
bonds (N1ϪH1···O1a): 282.0(2) pm) to each other, forming
centrosymmetrical dimers. In addition, a medium strong in-
tramolecular hydrogen bonding links the NH group to the
halide atom (N3ϪH2···Cl1: 311.3(2) pm). The dihedral
angle between the “best planes” of the ligand and the
CuClPS-moiety is 17° (see Fig 1).
The silver complex, 3, consists in contrast to the similar
silver complex containing AMTTO, which is an ionic com-
plex [(AMTTO)Ag(PPh3)2]NO3 [11], of neutral molecules
and possesses only C1-symmetry (Fig. 2). The ATT ligand
acts here as monodentate one and coordinates to the silver
atom through its sulfur atom. The silver atom is also sur-
rounded by two triphenylphosphane molecules and the co-
ordination of the nitrate ion completes the distorted tetra-
hedral coordination around it. This arrangement is con-
siderable distorted since the P angle at the metal site,
P1ϪAg1ϪP2 with a value of 128.24(3)°, is close to trig-
3 can be obtained by the reaction of AgNO3, PPh3 and
1 in a molar ratio 1:2:1 in methanol/chloroform [eq. (2)].
MeOH/CHCl3
1 ϩ AgNO3 ϩ 2 PPh3
Ǟ [(ATT)Ag(PPh3)2(NO3)] (2)
3
Both complexes are colorless compounds. The absorp-
tions νCuS and νCuCl of complex 2 can be observed at 340
and 284 cmϪ1, respectively. In the IR spectra of 3 a band
at 295 and 322 cmϪ1 can be assigned to νAgS and νAgO
[6]. The CϭO and CϭN functions cause two vibrations at
1687 and 1543 cmϪ1 for 2 and 1684 and 1552 cmϪ1 for 3,
respectively. PϪC vibrations of the moiety PPh3 are found
in the range 748Ϫ696 cmϪ1 for 2 and at 761Ϫ696 cmϪ1 for
3. The NO3Ϫ-moiety presents its NϪO asymmetric stretch-
ing mode at 1378 cmϪ1. For NϪH stretching vibrations two
broad weak absorptions could be found at 3477 (2) and
3490 (3) cmϪ1, a result of hydrogen bonding. Consistent
with the structures of 2 and 3, only one sharp singlet reson-
ance at Ϫ3.14 ppm and at 8.6 ppm were observed in each
of the 31P{1H] NMR spectra. The value for 2 is in good
agreement with the resonances of [Cu(PPh3)2Cl]
(Ϫ3.7 ppm) [7] and [Cu(PPh3)3][NO3] (Ϫ2.9 ppm) [8]. In
general, the coordination of the triphenylphosphane to cop-
per(I) causes no large shifts of the signal of the uncoordi-
nated phosphane at Ϫ6.0 ppm.[9]
3 Results and Discussion
The copper(I) complex consists of neutral molecules
(Fig. 1). The molecule of 2 posseses C1-symmetry. The co-
ordination around the metal atom is distorted trigonal
planar with one P atom of the phosphane molecule, one S
atom of the thione and one Cl atom. This arrangement is
considerable distorted since the angle P1ϪCu1ϪCl1 with a
value of 127.02(3)° is somewhat larger than the trigonally
Fig. 1 Structure of two molecules of 2 dimerized by hydrogen bonds (most of the H atoms are omitted for clarity; thermal ellipsoids
40% probability).
404
 2004 WILEY-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim
zaac.wiley-vch.de
Z. Anorg. Allg. Chem. 2004, 630, 403Ϫ406

Copper(I) and Silver(I) Complexes with ATT (ATT ϭ 6-Aza-2-thiothymine)
4 Experimental Section
The following chemicals were purchased and used without further
purification: CuCl, AgNO3, MeOH, CHCl3 and PPh3. 1 was pre-
pared according to the literature procedures [14]. The IR spectra
were obtained on a Bruker IFS-88 (nujol mulls: CsI discs of the
range 4000Ϫ500 cmϪ1; polyethylen discs for the range 500Ϫ100
cmϪ1).
The 31P NMR spectrum was measured on a Bruker instrument
AX-200 with 85% aqueous H3PO4 (external) as standard (δ ϭ 0.0
ppm)
[(ATT)CuCl(PPh3)] (2). Copper(I) chloride (0.12 g, 1 mmol) was
added to a solution of 1 (0.14 g, 1 mmol) in 10 mL of methanol
and stirred for 5 hrs at room temperature. To this solution was
added a solution of triphenylphosphane (0.26 g, 1 mmol) in 5 mL
of chloroform and stirred for further 2 hrs at room temperature.
The resulted crude was filtered and washed with cold methanol and
chloroform. Suitable single crystals for X-ray diffraction could be
obtained from the acetonitril solution of 2.
Yield: 0.45 g (90%)
Elemental analysis: C22H20ClCuN3OPS (504.44): calcd C 52.38, H
3.99, N 8.33, Cu 12.59, P 6.13, S 6.35; found C 51.98, H 3.88, N
8.30, Cu 12.33, P 6.01, S 6.28%.
Fig. 2 Molecular structure of 3 (most of the H atoms are omitted
for clarity; the phenyl rings are representated as thin lines only;
thermal ellipsoids 40% probability).
IR (Nujol; cmϪ1): 3477 vw (νNH, br), 1716 s, 1687 s (νCϭO), 1605 s, 1543
s (νCϭN, triazine), 1478 m, 1434 s, 1378 m, 1326 m, 1270 w, 1226 s, 1096 s,
748 s (νPPh3), 695 s (νPPh3), 579 s, 521 s, 502 s, 416 s, 340 s (νCuS), 285 s,
200 m (νCuCl), 175 (νCuP) m, 134 m.
31P NMR (d6-DMSO): Ϫ3.14 ppm.
onally coordinated AgI, while three other selected angles in
the AgP2SN group with 108.97(8)°(S1ϪAg1ϪO3),
109.47(3)°(S1ϪAg1ϪP2) and 108.2(1)°(P1ϪAg1ϪO3) are
nearly to those of a regular tetrahedron. The tetrahedral
distortion can be accounted for the steric hindrance in-
duced by the two bulky phosphane molecules and was ob-
served in analogous silver complexes such as
[(AMTTO)Ag(PPh3)2]NO3·0.5MeOH·0.5H2O [P1ϪAg1ϪP2:
126.95(3)°] [11] and [(C4H4N3SON(ϭCMe2)Ag(PPh3)2]-
NO3 (P1ϪAg1ϪP2: 124.33(6)°) [4b]. The AgϪP distances
mean 244.75 pm, are within the range observed in com-
plexes with four coordinated AgI containing two phos-
phanes (242.6Ϫ250.4 pm) [12]. The AgϪS bond lengths of
262.11(9) pm is significantly longer than the distance found
in [(AMTTO)2Ag]NO3 (243.50(8) pm], possessing a 2ϩ2
coordination around the Agϩ center and lies in the range
observed in [(AMTTO)Ag(PPh3)2]NO3·0.5MeOH·0.5H2O
(264.40(8) pm) [11] and [(C4H4N3SON(ϭCMe2)Ag(PPh3)2]-
NO3·0.5MeOH (262.9(2) pm) with four coordinated silver
atoms [4b]. The AgϪO distance of 256.0(3) pm lies in the
range observed in [Ag2(NO3)2(Ph2AsCH2CH2AsPh2)] [13].
The existence of a medium strong intramolecular hydro-
gen bond between the NH-group of the ligand and an oxy-
gen atom of the nitrate moiety [N1···O4: 285.0(5) pm] and
an intermolecular hydrogen bond between the other oxygen
atom of the nitrate molecule and the coordinated solvate
molecule (MeOH) [O3···O6: 277.7(4) pm)] also contribute
to the angular distortion about the silver atom and the ni-
trogen atom of the nitrate moiety. There is also a medium
strong intermolecular hydrogen bond between the NH-
group of the ligand and the oxygen atom of the solvate
molecule leading to chains along [010].
[(ATT)Ag(NO3)(PPh3)2]·MeOH (3). Silver nitrate (0.17 g, 1 mmol)
was added to a solution of 1 (0.14 g, 1 mmol) in 10 mL of methanol
and stirred for 3 hrs at room temperature. A solution of tri-
phenylphosphane (0.52 g, 2 mmol) in 10 mL of chloroform was
added dropwise to the reaction mixture and stirred for further 5
hrs at room temperature. The solvent was evaporated to a small
volume, the formed crude was filtered and washed with cold meth-
anol. The clear solution was kept at 4°C to give colorless crystals
of 3.
Yield: 0.71 g (85%)
Elemental analysis: C41H39AgN4O5P2S (869.64): calcd C 56.62, H
4.52, N 6.44, Ag 12.40, P 7.12, S 3.68; found C 55.89, H 4.43, N
6.35, Ag 12.29, P 7.00, S 3.59%.
IR (Nujol; cmϪ1): 3490 vw (νNH, br), 3183 s, 3132 s, 1717 s, 1684 s
(νCϭO), 1601 s, 1552 s (νCϭN, triazine), 1453 m, 1426 s, 1378 m, 1347 m,
1269 w, 1133 s, 1038 s, 791 s, 767 s (νPPh3), 721 s (νPPh3), 694 s (νPPh3),
582 s, 551 s, 446 s, 417 s, 409 s, 322 s (νAgO), 295 s (νAgS), 277 s.
31P NMR (d6-DMSO): 8.6 ppm.
Crystal structure analyses of 2 and 3
The crystals of 2 and 3 were covered with a perfluorinated oil and
mounted on the top of a glass capillary under a flow of cold gase-
ous nitrogen. The orientation matrix and preliminary unit cell di-
mensions were determined from ca. 1000 (2, 3; Stoe IPDS) reflec-
tions (graphite-monochromated Mo-Kα radiation (λ ϭ 71.073 pm)
for both complexes. The final cell parameters were determined from
15000 for 2 and from 20000 for 3. The intensities were corrected
for Lorentz and polarization effects. In addition, absorption correc-
tions were applied for 2 and 3 (numerical). The structures were
solved by the direct methods for 2 and 3 (SHELXS-97 [15] ) and
refined against F2 by full-matrix least-squares using the program
SHELXL-97 [16]. The hydrogen atoms (CϪH) in 2 and 3 were cal-
Z. Anorg. Allg. Chem. 2004, 630, 403Ϫ406
zaac.wiley-vch.de
 2004 WILEY-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim
405

M. Ghassemzadeh, M. M. Pooramini, M. Tabatabaee, M. M. Heravi
in 2 and H1 and H2 in 3). Programs used were SHELXTL-Plus
[17], SHELXL-97 [16], ORTEP [18], and PLATON [19, 20].
Table 1 Crystallographic data for 2 and 3
Compound
2
3
References
Empirical formula
Formula mass
Crystal size (mm)
Crystal system
Space group
a/pm
C22H20ClCuN3OPS C41H39AgN4O5P2S
[1] C.S. Stone, D.A. Weinberger, C.A. Mirkin, Prog. Inorg. Chem.
1999, 48, 223.
504.46
869.66
0.43 ϫ 0.21 ϫ 0.15
monoclinic
I2/a
0.48 ϫ 0.3 ϫ 0.21
monoclinic
P21/c
[2] a) M. Ghassemzadeh, K. Aghapoor, M.M. Heravi, B.
Neumüller, Z. Anorg. Allg. Chem. 1998, 624 1969; b) B. Neu-
müller, M.M. Heravi, M. Ghassemzadeh, Z. Anorg. Allg. Chem.
1999, 625, 1908; c) M. Ghassemzadeh, M. Boulortchian, S.
Chitsaz, B. Neumüller, M.M. Heravi, Eur. J. Inorg. Chem.
2000, 1877.
[3] R.G. Pearson, J. Am. Chem. Soc. 1963, 85, 3533.
[4] a) F. Adhami, M. Ghassemzadeh, M.M. Heravi, A. Taeb, B.
Neumüller, Z. Anorg. Allg. Chem. 1999, 625, 1411; b) M.
Ghassemzadeh, F. Adhami, M.M. Heravi, A. Taeb, S. Chitsaz,
B. Neumüller, Z. Anorg. Allg. Chem. 2001, 627, 815; c) M.
Ghassemzadeh, F. Adhami, M.M. Heravi, A. Taeb, S. Chitsaz,
B. Neumüller, Z. Anorg. Allg. Chem. 2002, 628, 2887.
[5] M. Ghassemzadeh, A. Sharifi, J. Malakootikhah, B. Neu-
müller, E. Iravani, submitted to Inorg. Chim. Acta, 2003.
[6] J. Weidlein, U. Müller, K. Dehnicke, Schwingungsfrequen-
zen II, 2. Aufl., G. Thieme Verlag, Stuttgart, 1986.
[7] T. Kräuter, B. Neumüller, Polyhedron 1996, 15, 2851
[8] P.F. Baron, J.C. Dyason, L.M. Engelhardt, P.C. Healy, A.H.
White, Aust. J. Chem.1985, 38, 261.
1159.3(1)
1143.2(1)
2208.2(1)
104.84(1)
4537.1(5)
8
1344.1(1)
1553.6(1)
1977,3(3)
105.26(1)
2330.7(4)
4
b/pm
c/pm
β/°
Volume/pm3·106
Z
dcalcd/g·cmϪ3
Absorption correction
µ/cmϪ1
1.477
1.45
numerical
12.6 (Mo-Kα)
193
numerical
6.9 (Mo-Kα)
193
Temperature/K
2θmax/°
52.58
52.61
Index range
h
k
l
Ϫ23 Ǟ 22
Ϫ14 Ǟ 14
Ϫ27 Ǟ 27
32256
Ϫ16 Ǟ 16
Ϫ19 Ǟ 19
Ϫ24 Ǟ 24
57206
8043 (0.0711)
6097
Reflections collected
Unique reflections (Rint
Reflections with Fo > 4 σ(Fo) 3735
Parameters
)
4571 (0.0606)
282
503
R1
0.0355
0.0959a
0.51
0.0436
wR2 (all data)
Max. electron density
/(e·pmϪ3)·10Ϫ6
0.1214[b]
0.98
a w ϭ 1/[σ2 (Fo)2 ϩ (0.0657·P)2 ϩ (4.39·P)], b w ϭ 1/[σ2 (Fo)2 ϩ (0.0847·P)2];
P ϭ [max (Fo2, 0) ϩ 2·Fc2]/3
[9] S. Berger, S. Braun, H.-O. Kalinowski, NMR-Spektroskopie
von Nichtmetallen, Vol. 3: 31P-NMR-Spektroskopie, Thieme,
Stuttgart 1993.
[10] G.A. Bowmaker, J.C. Dyason, P.C. Healy, L.M. Engelhardt,
C. Pakawatchai, A.H. White, J. Chem. Soc., Dalton Trans
1987, 1089 and references cited therein.
Table 2 Selected bond lengths/pm and angles/° of 2 and 3
2
[11] unpublished results.
Cu1ϪCl1
Cu1ϪS1
Cu1ϪP1
S1ϪC1
222.32(6)
226.50(6)
220.42(6)
168.2(2)
136.3(3)
137.2(3)
133.0(3)
136.7(3)
122.1(3)
Cl1ϪCu1ϪS1
Cl1ϪCu1ϪP1
S1ϪCu1ϪP1
Cu1ϪS1ϪC1
N3ϪC1ϪN1
117.62(3)
127.02(3)
114.86(3)
108.21(8)
115.6(2)
[12] a) D. Coucouvanis, N.C. Baenzinger, S.M. Johnson, Inorg.
Chem. 1974, 13, 1191; b) F.J. Hollander, D. Coucouvanis,
Inorg. Chem. 1974, 13, 2381; c) D.D. Heinrich, J.P. Fackler
(Jr.), P. Lahuerta, Inorg. Chim. Acta 1986, 116, 15; d) R. Ales-
sio, D. Belli Dell’Amico, F. Calderazzo, U. Englert, Gazz.
Chim. Ital. 1993, 123, 719.
C1ϪN1
N1ϪC2
C1ϪN3
N3ϪN2
C2ϪO1
[13] C. Pelizzi, G. Pelizzi, P. Tarasconi, J. Org. Chem. 1985, 281,
403.
[14] J. Gut, Collect. Czech. Chem. Commun. 1957, 51, 1947.
[15] G.M. Sheldrick, SHELXS-97, Universität Göttingen, 1997.
[16] G.M. Sheldrick, SHELXL-97, Göttingen, 1997.
[17] G.M. Sheldrick, SHELXTL-Plus, Release 4.2 for Siemens R3
Crystallographic Systems Analytical X-Ray Instruments Inc.,
Madison, WI, 1996.
3
Ag1ϪS1
Ag1ϪP1
Ag1ϪP2
Ag1ϪO3
S1ϪC1
C1ϪN1
C1ϪN3
N1ϪC2
N3ϪN2
C2ϪO1
262.11(9)
244.35(8)
245.16(8)
256.0(3)
168.5(3)
134.4(4)
133.0(4)
137.5(5)
137.3(4)
121.9(4)
S1ϪAg1ϪP1
S1ϪAg1ϪP2
S1ϪAg1ϪO3
O3ϪAg1ϪP1
Ag1ϪS1ϪC1
P1ϪAg1ϪP2
N1ϪC1ϪN3
O3ϪN4ϪO4
O3ϪN4ϪO5
O4ϪN4ϪO5
106.55(3)
109.47(3)
108.97(8)
108.2(1)
101.3(1)
128.24(3)
115.7(3)
115.3(3)
125.3(4)
119.3(4)
[18] C.K. Johnson, ORTEP, ORNL-3794, Oak Ridge National
Laboratory, Tennessee, 1965.
[19] A.L Spek, PLATON-98, Universiteit Utrecht, 1998.
[20] Further details can be obtained free of charge on application
to the Cambridge Crystallographic Data Center, 12 Union
Road, Cambridge CB2 1EZ, U.K. [Fax: (internat.) ϩ44
(0)1223 336033; E-mail: deposite@ccdc.cam.ac.uk] quoting
the depository nos. CCDC 224103 (2) and CCDC 224104 (3).
culated in ideal positions (CϪH: 95 pm; refinement with a common
displacement parameter for all H atoms except for H1, H2 and H3
406
 2004 WILEY-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim
zaac.wiley-vch.de
Z. Anorg. Allg. Chem. 2004, 630, 403Ϫ406