The hydrogen-bonded dimers of N,N′,N″-tricyclohexylphosphoric triamide in new tin(IV) and copper(II) complexes

Article abstract of DOI:10.1107/S010827011101403X

In the new tin(IV) and copper(II) complexes, cis-dichlorido-trans-dimethyl- cis-bis-(N,N′,N″-tricyclo-hexyl-phospho-ric triam-ide-κO) tin(IV), [Sn(CH₃)₂C₁₂(C₁₈H ₃₆N₃OP)₂], (I), and trans-diaqua-bis-(N, N′,N″-tricyclohexylphosphoric triamide-O)copper(II) dinitrate-N,N′,N″-tricyclohexylphosphoric triamide (1/2), [Cu(C ₁₈H₃₆N₃OP)₂(H₂O) ₂](NO₃)₂·2C₁₈H ₃₆N₃OP, (II), the N,N′,N″- tricyclohexylphospho-ric triamide (PTA) ligands exist as hydrogen-bonded dimers via P=O...H - N inter-actions around the metal center. The asymmetric unit in (I) consists of one complete complex mol-ecule located on a general position. The Sn^IV coordination geometry is octa-hedral with two cis hydrogen-bonded PTA ligands, two cis chloride ligands and two trans methyl groups. The asymmetric unit in (II) contains one half of a [Cu(PTA) ₂(H₂O)₂]²⁺ dication on a special position (site symmetry for the Cu atom), one nitrate anion and one free PTA mol-ecule, both on general positions. The complex adopts a square-planar trans-[CuO₂O₂] coordination geometry, with the Cu ^II ion coordinated by two PTA ligands and two water mol-ecules. Each of the noncoordinated PTA mol-ecules is hydrogen bonded to a neighboring coordinated PTA molecule and an adjacent water mol-ecule; the phosphoryl O atom acts as a double-H-atom acceptor. The P atoms in the PTA ligands of both complexes and in the noncoordinated hydrogen-bonded mol-ecules in (II) adopt a slightly distorted tetra-hedral environment.

Full text of DOI:10.1107/S010827011101403X

metal-organic compounds
Acta Crystallographica Section C
Crystal Structure
Communications
P
Oꢀ ꢀ ꢀM bond (Gholivand et al., 2006). Here we discuss two
cases where this type of hydrogen bond remains in a coordi-
nated phosphoric triamide ligand in two new complexes and
consider its possible role in the coordination mode of the
ligand.
ISSN 0108-2701
The hydrogen-bonded dimers of
N,N0,N00-tricyclohexylphosphoric
triamide in new tin(IV) and copper(II)
complexes
Mehrdad Pourayoubi,a* James A. Golen,b Mahnaz
Rostami Chaijan,a Vladimir Divjakovic,c Monireh Negaria
and Arnold L. Rheingoldb
aDepartment of Chemistry, Ferdowsi University of Mashhad, Mashhad 91779, Iran,
bDepartment of Chemistry, University of California, San Diego, 9500 Gilman Drive,
La Jolla, CA 92093, USA, and cDepartment of Physics, Faculty of Sciences,
University of Novi Sad, Trg D. Obradovica 3, 21000 Novi Sad, Serbia
Correspondence e-mail: mehrdad_pourayoubi@yahoo.com
Received 2 January 2011
Accepted 13 April 2011
Online 28 April 2011
In the new tin(IV) and copper(II) complexes, cis-dichlorido-
trans-dimethyl-cis-bis(N,N0,N00-tricyclohexylphosphoric triam-
ide-ꢀO)tin(IV), [Sn(CH3)2Cl2(C18H36N3OP)2], (I), and trans-
diaquabis(N,N0,N00-tricyclohexylphosphoric triamide-ꢀO)cop-
per(II) dinitrate–N,N0,N00-tricyclohexylphosphoric triamide
(1/2), [Cu(C18H36N3OP)2(H2O)2](NO3)2ꢀ2C18H36N3OP, (II),
the N,N0,N00-tricyclohexylphosphoric triamide (PTA) ligands
exist as hydrogen-bonded dimers via P Oꢀ ꢀ ꢀH—N inter-
actions around the metal center. The asymmetric unit in (I)
consists of one complete complex molecule located on a
general position. The SnIV coordination geometry is octa-
hedral with two cis hydrogen-bonded PTA ligands, two cis
chloride ligands and two trans methyl groups. The asymmetric
unit in (II) contains one half of a [Cu(PTA)2(H2O)2]2+
dication on a special position (site symmetry 1 for the Cu
atom), one nitrate anion and one free PTA molecule, both on
general positions. The complex adopts a square-planar trans-
[CuO2O2] coordination geometry, with the CuII ion coordi-
nated by two PTA ligands and two water molecules. Each of
the noncoordinated PTA molecules is hydrogen bonded to a
neighboring coordinated PTA molecule and an adjacent water
molecule; the phosphoryl O atom acts as a double-H-atom
acceptor. The P atoms in the PTA ligands of both complexes
and in the noncoordinated hydrogen-bonded molecules in (II)
adopt a slightly distorted tetrahedral environment.
Organotin(IV) complexes, particularly those with organo-
phosphorus ligands, have attracted attention because of their
versatile biological properties (Gholivand et al., 2010). Similar
to organophosphorus ligands, phosphoramides are suitable for
reacting with organotin(IV) compounds. In this series, a few
organotin(IV)–phosphoramide compounds have been re-
ported with some phosphoramide ligands. A search of the
Cambridge Structural Database (CSD, Version 5.32, Novem-
ber 2010 update; Allen, 2002) shows that in all reported
dialkyltin(IV) dihalide tris(alkylamido)phosphate com-
pounds, the phosphoramide ligands adopt a trans arrange-
ment. We present here the first structure of this class of
organotin(IV) complexes with two phosphoric triamide
ligands in cis positions (Fig. 1). The Sn coordination geometry
in cis-dichlorido-trans-dimethyl-cis-bis(N,N0,N00-tricyclohexyl-
phosphoric triamide-ꢀO)tin(IV), (I), is octahedral with the
N,N0,N00-tricyclohexylphosphoric triamide (PTA) and chloride
ligands cis, but with the methyl groups trans (Fig. 1 and
Table 1). The P atoms in the PTA ligands adopt a slightly
distorted tetrahedral environment. The Sn—O—P angles are
both slightly greater than 140ꢁ. These geometric parameters
are consistent with those observed in related structures:
[(Me2N)3PO]2X2Me2Sn, with X = Br (CSD refcode BDMSAP;
Aslanov et al., 1977), Cl (CDMSAP01; Rheingold et al., 1984);
[(Me2N)3PO]2X2Et2Sn, with X = I (DUCJAM; Tursina et al.,
Comment
The P Oꢀ ꢀ ꢀH—N hydrogen bond exists in the structures of
phosphoramide compounds containing the P(O)NH moiety.
In the process of coordination to a metal cation (M), one
would anticipate that this interaction would be replaced with a
m160 # 2011 International Union of Crystallography
doi:10.1107/S010827011101403X
Acta Cryst. (2011). C67, m160–m164

metal-organic compounds
The two symmetry-independent PTA ligands in (I) are
involved in an intramolecular N2—H2Nꢀ ꢀ ꢀO2—P2 hydrogen
bond (Table 2) in which the amide group of one ligand (P1)
interacts with the phosphoryl O atom of the other ligand. This
hydrogen bond may be considered as a factor helping to
stabilize the previously unobserved cis geometry. The P2—O2
bond length is a little longer than the P1—O1 bond length, the
latter O atom not serving as a hydrogen-bond acceptor. An
intramolecular N5—H5Nꢀ ꢀ ꢀCl2 hydrogen bond is also found
in the structure. The environment of each N atom in the PTA
ligands is almost planar and it does not form any hydrogen
bonds as an acceptor, showing its low Lewis-base character. In
previously reported phosphoramide compounds and their
dialkyl dichloride tin(IV)–phosphoramide complexes (Gholi-
vand et al., 2004, 2006; Gholivand & Shariatinia, 2006), the
N—Hꢀ ꢀ ꢀO hydrogen bonds which appear in the structures of
the free phosphoramide molecules are replaced by N—Hꢀ ꢀ ꢀCl
hydrogen bonds in the complexes, as the phosphoryl O atoms
are involved in Sn—O covalent bonds in the latter. This fact
may be supported by IR spectroscopy in which the N—H
stretching frequencies in the tin complexes are higher than in
the free molecules as they are involved in weaker N—Hꢀ ꢀ ꢀCl
hydrogen bonds.
Figure 1
The molecular structure and atom-labeling scheme for (I), with
displacement ellipsoids drawn at the 50% probability level. Intra-
molecular hydrogen bonds are shown as thin dotted lines.
The two-dimensional hydrogen-bonded network in (I) is
produced via some different weak N—Hꢀ ꢀ ꢀCl hydrogen bonds
between the complex and three neighboring complexes in the
crystal (Fig. 2). In this case, the Cl1 and Cl2 atoms are,
respectively, involved in N6—H6Nꢀ ꢀ ꢀCl1ii and N4—H4Nꢀ ꢀ ꢀ
1985), Br (FILCIM and FILCIM01; Tursina et al., 1987); [R2-
{PhC(O)NH}PO]2Cl2Me2Sn (Gholivand & Shariatinia, 2006),
with R = t-BuNH (YERGEI), C4H8N (YERGIM), C5H10N
(YERGOS) and (Me)(Cy)N (Cy is cyclohexyl; YERGUY);
{(C5H10N)2[(p-F-Ph)C(O)NH]PO}2Cl2Me2Sn (LEHWIF; Gholi-
vand et al., 2006).
ii
1
2
1
2
Cl2 interactions [symmetry code: (ii) x ꢂ , ꢂy + 12, z ꢂ ] to
build an R22(8) ring (Etter et al., 1990; Bernstein et al., 1995).
Figure 2
A view of the crystal packing of (I). Hydrogen bonds are shown as thin dotted lines. H atoms on C atoms are not shown for clarity. [Symmetry codes: (i)
1
2
1
2
1
2
ꢂx + 2, ꢂy, ꢂz + 1; (ii) x ꢂ , ꢂy + , z ꢂ .]
ꢃ
Acta Cryst. (2011). C67, m160–m164
Pourayoubi et al.
[Sn(CH3)2Cl2(PTA)2] and [Cu(PTA)2(H2O)2](NO3)2ꢀ2PTA m161

metal-organic compounds
Copper complexes have been of interest as the interface
between biochemistry and coordination chemistry (Collinson
& Fenton, 1996; Hossain et al., 1996; Tarafder et al., 2002). The
PTA ligand was also used to prepare a new copper(II)
phosphoramidate complex, namely trans-diaquabis(N,N0,N00-
tricyclohexylphosphoric triamide-ꢀO)copper(II) dinitrate–
N,N0,N00-tricyclohexylphosphoric triamide (1/2), (II) (Fig. 3).
The asymmetric unit contains one half of a [Cu(PTA)2-
(H2O)2]2+ dication, one nitrate anion and one free PTA mol-
ecule. The CuII ion is located on a crystallographic inversion
center. The complex thus adopts a square-planar trans-
[CuO2O2] coordination geometry, with the CuII ion coordi-
nated by two PTA ligands and two water molecules. The
phosphoryl O atom makes a shorter Cu—O bond than the
water O atom (Table 3). The P atoms in the PTA ligands adopt
a
slightly distorted tetrahedral environment and the
Cu—O—P angle is a little under 140ꢁ. These geometric
parameters are consistent with those in related structures:
[Cu4OCl6{(O)P(NHtBu)3}4] (LIDNIW; Fu & Chivers, 2007),
[Cu(ONO2)2{(O)P(NHtBu)3}2] (LIDPAQ; Fu & Chivers,
2007) and [CuCl2(NHC4H8O){(O)P(NMe2)3} (YIBZEP; Xie
et al., 2007).
Figure 3
The molecular structure of (II), with displacement ellipsoids drawn at the
50% probability level. Hydrogen bonds are shown as thin dotted lines.
[Symmetry code: (i) ꢂx + 1, ꢂy + 1, ꢂz + 1.]
Each of the noncoordinated PTA molecules is hydrogen
bonded to a neighboring coordinated PTA molecule via an
N2—H2Nꢀ ꢀ ꢀO3i hydrogen bond [Table 4; symmetry code: (i)
ꢂx + 1, ꢂy + 1, ꢂz + 1] and to an adjacent water molecule via
an O2—H2WBꢀ ꢀ ꢀO3 hydrogen bond. The noncoordinated
PTA phosphoryl O atom thus acts as a double-H-atom
acceptor (Steiner, 2002). Atom O5 of the nitrate anion co-
The Cl2 atom is also involved in an intramolecular N—Hꢀ ꢀ ꢀCl
hydrogen bond, which has been noted earlier, while the Cl1
atom co-operates in another intermolecular N3—H3Nꢀ ꢀ ꢀCl1i
hydrogen bond [symmetry code: (i) ꢂx + 2, ꢂy, ꢂz + 1]
(Table 2).
Figure 4
A view of the centrosymmetric hydrogen-bonded pentamer containing one [Cu(PTA)2(H2O)2]2+ dication (green in the electronic version of the paper),
two PTA molecules (red) and two nitrate anions (blue); the two other nitrate anions in the top right and bottom left of the figure, which co-operate in two
weak N5—H5Nꢀ ꢀ ꢀO4ii and N5—H5Nꢀ ꢀ ꢀO6ii hydrogen bonds, assemble neighboring pentamers in a two-dimensional array. Hydrogen bonds are shown
1
1
1
as thin dotted lines. [Symmetry codes: (i) ꢂx + 1, ꢂy + 1, ꢂz + 1; (ii) x ꢂ , ꢂy + , z ꢂ .]
2
2
2
ꢃ
m162 Pourayoubi et al. [Sn(CH3)2Cl2(PTA)2] and [Cu(PTA)2(H2O)2](NO3)2ꢀ2PTA
Acta Cryst. (2011). C67, m160–m164

metal-organic compounds
DMSO-d6, 300.0 K, TMS): ꢁ 1.02 (s, 6H, CH3), 1.13 (m, 30H), 1.49 (m,
6H), 1.63 (m, 12H), 1.79 (m, 12H), 2.80 (m, 6H, CH), 3.49 (b, 6H,
NH). 13C NMR (125.75 MHz, DMSO-d6, 300.0 K, TMS): ꢁ 22.95 (s,
3
CH3), 25.01 (s), 25.23 (s), 35.48 [d, J(P,C) = 4.7 Hz], 49.48 (s).
For the synthesis of [Cu(PTA)2(H2O)2](NO3)2ꢀ2PTA, (II), a
solution of copper(II) nitrate trihydrate (0.547 g, 2.26 mmol) in
CH3CN (5 ml) was added dropwise to a solution of PTA (1.423 g,
4.17 mmol) in ethanol (10 ml). The resulting clear solution was stirred
for 2 h at room temperature. Single crystals were obtained from a
mixture of dimethylformamide/ethanol after slow evaporation at
room temperature (yield: approximately 30%). IR (KBr, cmꢂ1): 3345,
3273, 2925, 2847, 1650, 1432, 1394, 1232, 1101, 1028, 950, 882, 828. 13C
NMR (125.75 MHz, DMSO-d6, 300.0 K, TMS): ꢁ 26.13 (s), 37.02 (s),
41.96 (b), 49.29 (s).
Compound (I)
Crystal data
3
˚
[Sn(CH3)2Cl2(C18H36N3OP)2]
Mr = 902.59
V = 4550.0 (4) A
Z = 4
Monoclinic, P21=n
Mo Kꢃ radiation
ꢄ = 0.79 mmꢂ1
T = 100 K
0.35 ꢄ 0.25 ꢄ 0.25 mm
˚
a = 12.0882 (6) A
˚
b = 25.1607 (13) A
˚
c = 15.8103 (8) A
ꢂ = 108.879 (1)ꢁ
Figure 5
The two-dimensional arrangement of molecules in the structure of (II)
viewed along the (101) plane.
Data collection
Bruker SMART APEXII CCD
area-detector diffractometer
Absorption correction: multi-scan
(APEX2; Bruker, 2005)
71686 measured reflections
12101 independent reflections
10758 reflections with I > 2ꢅ(I)
Rint = 0.030
operates in O2—H2WAꢀ ꢀ ꢀO5, N3—H3Nꢀ ꢀ ꢀO5 and N4—
H4Nꢀ ꢀ ꢀO5 hydrogen bonds, respectively, with neighboring
coordinated water, and coordinated and noncoordinated PTA
molecules (Fig. 4 and Table 4). Moreover, atom O4 of the
nitrate anion co-operates in hydrogen-bonding interactions
with N1—H1N and N3—H3N groups of the adjacent coordi-
nated PTA. These interactions make a centrosymmetric
hydrogen-bonded pentamer containing one dication, two PTA
molecules and two nitrate anions. The N5—H5N group of free
PTA molecules is involved in two weak hydrogen bonds, viz.
N5—H5Nꢀ ꢀ ꢀO4ii and N5—H5Nꢀ ꢀ ꢀO6ii [symmetry code: (ii)
Tmin = 0.772, Tmax = 0.825
Refinement
R[F2 > 2ꢅ(F2)] = 0.024
wR(F2) = 0.080
S = 1.00
462 parameters
H-atom parameteꢂrs3 constrained
˚
Áꢆmax = 0.84 e A
Áꢆmin = ꢂ0.48 e A
ꢂ3
˚
12101 reflections
Compound (II)
1
2
1
2
x ꢂ , ꢂy + 12, z ꢂ ] (Fig. 4). These hydrogen bonds assemble
Crystal data
[Cu(C18H36N3OP)2(H2O)2](NO3)2ꢀ-
ꢂ = 116.656 (1)ꢁ
˚
V = 4264.5 (6) A
Z = 2
the centrosymmetric pentamers in
arrangement along the (101) plane (Fig. 5).
a two-dimensional
3
2C18H36N3OP
Mr = 1589.46
Monoclinic, P21=n
Mo Kꢃ radiation
ꢄ = 0.39 mmꢂ1
T = 100 K
0.24 ꢄ 0.20 ꢄ 0.18 mm
˚
a = 15.4495 (12) A
˚
b = 18.6924 (14) A
Experimental
˚
c = 16.5229 (12) A
N,N0,N00-Tricyclohexylphosphoric triamide (PTA) was prepared
according to the procedure reported by Audrieth & Toy (1942). IR
(KBr, cmꢂ1): 3272 (NH), 2930, 2852, 2667, 1659, 1440, 1296, 1237,
1145, 1111, 1004, 926, 882. For the synthesis of [Sn(CH3)2Cl2(PTA)2],
(I), a solution of dimethyltin(IV) dichloride (0.253 g, 1.15 mmol) in
chloroform (5 ml) was added dropwise to a solution of PTA (0.787 g,
2.30 mmol) in chloroform (15 ml). The clear solution was stirred for
5 h. Colorless crystals were obtained after a few days in a refrigerator
(at 278 K). An effort to prepare the trans complex under reflux
conditions (24 h) in CH3OH was not successful and led to the cis
complex, which was confirmed by X-ray crystallography (yield:
approximately 80%). IR (KBr, cmꢂ1): 3285 (NH), 2921, 2852, 1444,
1301, 1242, 1112, 1023, 936, 792. 31P{1H} NMR (202.45 MHz, DMSO-
d6, 300.0 K, H3PO4 external): ꢁ 12.83 (s). 1H NMR (500.13 MHz,
Data collection
Bruker APEXII CCD
diffractometer
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
Tmin = 0.911, Tmax = 0.932
32668 measured reflections
9496 independent reflections
7117 reflections with I > 2ꢅ(I)
Rint = 0.054
Refinement
R[F2 > 2ꢅ(F2)] = 0.043
wR(F2) = 0.106
S = 1.04
9496 reflections
490 parameters
9 restraints
H atoms treated by a mixture of
independent and constrained
refinement
ꢂ3
˚
Áꢆmax = 0.47 e A
ꢂ3
˚
Áꢆmin = ꢂ0.51 e A
ꢃ
Acta Cryst. (2011). C67, m160–m164
Pourayoubi et al.
[Sn(CH3)2Cl2(PTA)2] and [Cu(PTA)2(H2O)2](NO3)2ꢀ2PTA m163

metal-organic compounds
˚
were normalized at standard values of 0.98–1.00 A, depending on the
Table 1
Selected geometric parameters (A, ) for (I).
ꢁ
˚
hybridization. All the H atoms were treated as riding atoms with their
Uiso(H) parameters equal to 1.5Ueq(C) for methyl H atoms and
1.2Ueq(C) otherwise. For (II), H atoms on N and O atoms were found
in difference Fourier maps and were allowed to refine with N—H =
Sn1—C38
Sn1—O1
Sn1—Cl1
2.1114 (16)
2.2281 (11)
2.5479 (4)
P1—O1
P1—N1
P2—O2
1.5032 (11)
1.6397 (14)
1.5116 (11)
˚
˚
˚
0.86 (1) A, O—H = 0.84 (1) A and H2WAꢀ ꢀ ꢀH2WB = 1.20 (2) A, and
with isotropic displacement parameters fixed at 1.2Ueq of the parent
atom. All other H atoms were placed in calculated positions and
C38—Sn1—C37
C38—Sn1—O1
O1—Sn1—O2
C38—Sn1—Cl1
O2—Sn1—Cl1
O1—P1—N3
176.31 (6)
90.69 (6)
87.31 (4)
90.83 (5)
176.07 (3)
117.82 (7)
106.76 (7)
117.89 (7)
O2—P2—N6
P1—O1—Sn1
P2—O2—Sn1
C1—N1—P1
C7—N2—P1
C13—N3—P1
C19—N4—P2
C25—N5—P2
107.63 (6)
142.63 (7)
144.10 (6)
128.23 (11)
123.14 (10)
120.32 (10)
124.77 (10)
122.46 (11)
˚
included as riding atoms, with C—H = 1.00 (CH) or 0.99 A (CH2) and
Uiso(H) = 1.2Ueq(C).
For both compounds, data collection: APEX2 (Bruker, 2005). Cell
refinement: APEX2 for (I); SAINT (Bruker, 2008) for (II). Data
reduction: APEX2 for (I); SAINT for (II). Program(s) used to solve
structure: SHELXTL (Sheldrick, 2008) for (I); SHELXS97 (Shel-
drick, 2008) for (II). Program(s) used to refine structure: SHELXTL
for (I); SHELXL97 (Sheldrick, 2008) for (II). For both compounds,
molecular graphics: Mercury (Macrae et al., 2008); software used to
prepare material for publication: SHELXTL.
O1—P1—N2
O2—P2—N4
Table 2
Hydrogen-bond geometry (A, ) for (I).
ꢁ
˚
D—Hꢀ ꢀ ꢀA
D—H
Hꢀ ꢀ ꢀA
Dꢀ ꢀ ꢀA
D—Hꢀ ꢀ ꢀA
Support of this investigation by the Ferdowsi University of
Mashhad is gratefully acknowledged.
N2—H2Nꢀ ꢀ ꢀO2
N3—H3Nꢀ ꢀ ꢀCl1i
N4—H4Nꢀ ꢀ ꢀCl2ii
N5—H5Nꢀ ꢀ ꢀCl2
N6—H6Nꢀ ꢀ ꢀCl1ii
0.86
0.92
0.88
0.83
0.87
2.16
2.61
2.46
2.51
2.53
2.9900 (16)
3.4403 (13)
3.3296 (12)
3.3135 (15)
3.3736 (14)
161
151
169
162
165
Supplementary data for this paper are available from the IUCr electronic
archives (Reference: SQ3282). Services for accessing these data are
described at the back of the journal.
1
2
1
1
Symmetry codes: (i) ꢂx þ 2; ꢂy; ꢂz þ 1; (ii) x ꢂ ; ꢂy þ ; z ꢂ .
2
2
Table 3
Selected geometric parameters (A, ) for (II).
ꢁ
˚
References
Allen, F. H. (2002). Acta Cryst. B58, 380–388.
Aslanov, L. A., Ionov, V. M., Attiya, V. M., Permin, A. B. & Petrosyan, V. S.
(1977). Zh. Strukt. Khim. 18, 1103–1113.
Audrieth, L. F. & Toy, A. D. F. (1942). J. Am. Chem. Soc. 64, 1553–1555.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem.
Int. Ed. Engl. 34, 1555–1573.
P1—O1
P1—N2
P1—N3
P1—N1
Cu1—O1
1.5090 (14)
1.6240 (17)
1.6274 (18)
1.6372 (17)
1.8888 (12)
Cu1—O2
P2—O3
P2—N5
P2—N6
P2—N4
1.9229 (15)
1.5024 (15)
1.6288 (16)
1.6348 (17)
1.6495 (17)
Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2008). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2009). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Collinson, S. R. & Fenton, D. E. (1996). Coord. Chem. Rev. 148, 19–40.
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256–
262.
Fu, Z. & Chivers, T. (2007). Can. J. Chem. 85, 358–365.
Gholivand, K., Farshadian, S., Hosseini, Z., Khajeh, K. & Akbari, N. (2010).
Appl. Organomet. Chem. 24, 700–707.
O1—P1—N2
O1—P1—N3
N2—P1—N3
O1—P1—N1
N2—P1—N1
N3—P1—N1
O1—Cu1—O2
103.41 (8)
118.43 (9)
106.46 (9)
111.53 (8)
115.45 (9)
102.03 (9)
91.42 (6)
P1—O1—Cu1
O3—P2—N5
O3—P2—N6
N5—P2—N6
O3—P2—N4
N5—P2—N4
N6—P2—N4
139.13 (9)
106.71 (8)
114.77 (9)
107.65 (8)
116.43 (8)
110.75 (9)
100.25 (8)
Gholivand, K., Pourayoubi, M. & Mostaanzadeh, H. (2004). Anal. Sci. 20, x51–
x52.
Gholivand, K. & Shariatinia, Z. (2006). J. Organomet. Chem. 691, 4215–
4224.
Gholivand, K., Shariatinia, Z. & Pourayoubi, M. (2006). Polyhedron, 25, 711–
721.
Hossain, M. E., Alam, M. N., Begum, J., Akbar Ali, M., Nazimuddin, M.,
Smith, F. E. & Hynes, R. C. (1996). Inorg. Chim. Acta, 249, 207–213.
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P.,
Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P.
A. (2008). J. Appl. Cryst. 41, 466–470.
Rheingold, A. L., Ng, S. W. & Zuckerman, J. J. (1984). Inorg. Chim. Acta, 86,
179–183.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Steiner, T. (2002). Angew. Chem. Int. Ed. 41, 48–76.
Tarafder, M. T. H., Jin, K. T., Crouse, K. A., Ali, A. M., Yamin, B. M. & Fun,
H.-K. (2002). Polyhedron, 21, 2547–2554.
Table 4
Hydrogen-bond geometry (A, ) for (II).
ꢁ
˚
D—Hꢀ ꢀ ꢀA
D—H
Hꢀ ꢀ ꢀA
Dꢀ ꢀ ꢀA
D—Hꢀ ꢀ ꢀA
N1—H1Nꢀ ꢀ ꢀO4
N3—H3Nꢀ ꢀ ꢀO5
N3—H3Nꢀ ꢀ ꢀO4
O2—H2WAꢀ ꢀ ꢀO5
O2—H2WBꢀ ꢀ ꢀO3
N2—H2Nꢀ ꢀ ꢀO3i
N4—H4Nꢀ ꢀ ꢀO5
N5—H5Nꢀ ꢀ ꢀO6ii
N5—H5Nꢀ ꢀ ꢀO4ii
N6—H6Nꢀ ꢀ ꢀO6
0.85 (1)
0.85 (1)
0.85 (1)
0.82 (1)
0.83 (1)
0.85 (1)
0.85 (1)
0.84 (1)
0.84 (1)
0.84 (1)
2.28 (1)
2.45 (1)
2.47 (1)
1.99 (1)
1.77 (1)
2.18 (1)
2.23 (1)
2.43 (1)
2.73 (2)
2.46 (1)
3.064 (2)
3.199 (2)
3.232 (2)
2.811 (2)
2.5926 (19)
2.983 (2)
3.050 (2)
3.244 (2)
3.359 (2)
3.258 (2)
154 (2)
148 (2)
149 (2)
175 (2)
170 (2)
159 (2)
163 (2)
164 (2)
133 (2)
159 (2)
Tursina, A. I., Aslanov, L. A., Chernyshev, V. V., Medvedev, S. V. & Yatsenko,
A. V. (1985). Koord. Khim. 11, 696–701.
1
2
1
2
1
2
Symmetry codes: (i) ꢂx þ 1; ꢂy þ 1; ꢂz þ 1; (ii) x ꢂ ; ꢂy þ ; z ꢂ .
Tursina, A. I., Medvedev, S. V., Yatsenko, A. V. & Aslanov, L. A. (1987). Zh.
Strukt. Khim. 28, 90–97.
Xie, D.-M., Ma, X.-J., Feng, W.-J., Shu, Z. & Jin, Z.-M. (2007). Acta Cryst. E63,
m1473–m1475.
For (I), N-bonded H atoms were found in difference Fourier maps.
C-bonded H-atom positions were calculated, and the C—H distances
ꢃ
m164 Pourayoubi et al. [Sn(CH3)2Cl2(PTA)2] and [Cu(PTA)2(H2O)2](NO3)2ꢀ2PTA
Acta Cryst. (2011). C67, m160–m164