Regio- and stereoselective addition of imides to ethyl 3-phenyl-2- propynoate in the presence of triphenylphosphine. Single crystal X-ray structure of ethyl (Z)-2-(1,3-dioxo-1,3,3a,4,7,7a-hexahydro-2H-isoindol2-yl)-3-phenyl-2- propenoate

Article abstract of DOI:10.1515/znb-2007-0612

A one-pot synthesis of sterically congested N-vinyl imides in fairly high yields by the reaction of ethyl 3-phenyl-2-propynoate, imides and triphenylphosphine is reported. The structures of these compounds were confirmed by IR, ¹H, and ^13<

Full text of DOI:10.1515/znb-2007-0612

Regio- and Stereoselective Addition of Imides to Ethyl 3-Phenyl-2-
propynoate in the Presence of Triphenylphosphine. Single Crystal X-Ray
Structure of Ethyl (Z)-2-(1,3-Dioxo-1,3,3a,4,7,7a-hexahydro-2H-isoindol-
2-yl)-3-phenyl-2-propenoate
Amir Tofangchi Mahyaria, Nahid Shajaria,b, Ali Reza Kazemizadeha,b
Katarzyna Slepokura , Tadeusz Lis , and Ali Ramazani
,
c
c
a
´
a Department of Chemistry, the University of Zanjan, P O Box 45195-313, Zanjan, Iran
b Department of Chemistry, Islamic Azad University–Zanjan Branch, P O Box 49195-467, Zanjan,
Iran
c Faculty of Chemistry, University of Wrocław, 14 Joliot-Curie St., 50-383 Wrocław, Poland
Reprint requests to Dr. A. Ramazani. Fax: +98 241 5283100. E-mail: aliramazani@yahoo.com
Z. Naturforsch. 2007, 62b, 829 – 834; received February 1, 2007
A one-pot synthesis of sterically congested N-vinyl imides in fairly high yields by the reaction
of ethyl 3-phenyl-2-propynoate, imides and triphenylphosphine is reported. The structures of these
compounds were confirmed by IR, 1H, and 13C NMR spectroscopy, and by a single crystal X-ray
structure determination. The structural analysis of the products indicated that the reaction is regio-
and stereoselective.
Key words: Phosphorus Ylide, Ethyl 3-Phenyl-2-propynoate, Vinyltriphenylphosphonium Salts,
Crystal Structure, N-Vinyl Imide
Introduction
from a phosphine and an alkyl halide. Phosphonium
salts are also prepared by Michael addition of phos-
phorus nucleophiles to activated olefins and in other
ways [4]. The phosphonium salts are most often con-
verted to the ylide by treatment with a strong base,
though weaker bases can be used if the salt is acidic
enough. In recent years, we have established a one-
pot method for the synthesis of stabilized ylides [5 – 8].
In this paper, we wish to describe the preparation and
– for one example – the single crystal X-ray structure
of sterically congested N-vinyl imides from the ethyl
3-phenyl-2-propynoate and imides in the presence of
triphenylphosphine in fairly high yields.
β-Additions of nucleophiles to the vinyl group of
vinylic phosphonium salts leading to the formation
of new alkylidenephosphoranes has attracted much at-
tention as a very convenient and synthetically useful
method in organic synthesis [1]. Organophosphorus
compounds have been extensively used in organic syn-
thesis as useful reagents as well as important ligands
in a number of transition metal catalysts [2]. Phospho-
rus ylides are a special type of zwitterions, which bear
a strongly nucleophilic, electron-rich carbanion-like
function adjacent to a phosphonium center. The elec-
tron distribution around the P+–C− bond and its con-
sequent chemical implications have been probed and
assessed through theoretical, spectroscopic and crys-
tallographic investigations [1]. The nucleophilicity at
Results and Discussion
Compound 5 may result from initial addition of
the ylidic carbon is a factor of essential mechanistic triphenylphosphine (1) to ethyl 3-phenyl-2-propynoate
importance in the use of phosphorus ylides as Wittig (2) and concomitant protonation of the 1 : 1 adduct 3,
reagents. These are important reagents in synthetic or- followed by the attack of the NH-acidic anion on the
ganic chemistry, especially in the synthesis of natu- vinyltriphenylphosphonium cation to form the phos-
rally occurring products, compounds with biological phorane 6 (Scheme 1) which undergoes intramolecular
and pharmacological activity [3]. These ylides are usu- proton transfer leading to the formation of sterically
ally prepared by treatment of a phosphonium salt with congested N-vinyl imides 8 via the zwitterionic inter-
a base, and phosphonium salts are usually obtained mediate 7. In this reaction triphenylphosphine acts as
0932–0776 / 07 / 0600–0829 $ 06.00 © 2007 Verlag der Zeitschrift fu¨r Naturforschung, Tu¨bingen · http://znaturforsch.com
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A. T. Mahyari et al. · Addition of Imides to Ethyl 3-Phenyl-2-propynoate in the Presence of Triphenylphosphine
Scheme 1.
a catalyst. We reduced the amount of triphenylphos-
phine to 50 % molar ratio. In all cases where we have
used triphenylphosphine as a catalyst in the range of
50 % to 100 % molar ratio, the reaction time amounted
to 48 h. In all cases where we have used triphenylphos-
phine as a catalyst in a molar ratio below 50 %, the
reaction time was longer than 48 h. In the absence
of triphenylphosphine no product formation was ob-
served. The NMR spectra indicated that solutions of
compounds 8a – b (CDCl3 as solvent) contained only
the Z isomer. However, in the case of 8c the NMR spec-
tra indicated that solutions of the compound (CDCl3 as
solvent) contained two isomers (E and Z). The relative
percentages of rotamers of 8c in CDCl3 were deter-
mined from the 1H NMR spectra. The structures 8a – c
were deduced from their IR, 1H and 13C NMR spectra.
Fig. 1. The molecular structure of compound 8c showing
the atom numbering scheme and the intramolecular C(5)–
H(5)···O(2) and C(7)–H(7)···N(1) contacts forming S(5)
and S(6) motifs, respectively (dotted lines). Displacement el-
lipsoids are shown at the 50 % probability level.
Description of the crystal and molecular structure
of 8c
˚
2 with r.m.s. = 0.060 A]. The atoms which deviate
the most from these planes are C(7) [being displaced
Crystals of 8c are built up from molecules the struc-
ture of which is shown in Fig. 1. Table 1 contains a
summary of the crystallographic data. Two well de-
fined planes (with the atom C(4) being common) may
be distinguished in the molecule of 8c. These are ethyl
(2Z)-2-amino-3-phenylacrylate [forming plane 1 with
˚
by 0.148(1) A from plane 1] and N(1) [deviating by
˚
0.138(1) A from plane 2]. The dihedral angle between
the least-squares plane 1 and plane 2 is 83.8(1)◦, so the
two planes are almost perpendicular to each other.
The molecule adopts a Z geometry with respect to
˚
a r.m.s. deviation of fitted atoms of 0.085 A] and the the C(4)–C(5) double bond, which is reflected in the
five-membered pyrrolidine-2,5-dione part of the tetra- value of the torsion angle N(1)–C(4)–C(5)–C(6) of
hydrophthalimidemoiety [along with atom C(4); plane −0.2(2)◦ (Table 2). The carbonyl atom O(1) of the
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A. T. Mahyari et al. · Addition of Imides to Ethyl 3-Phenyl-2-propynoate in the Presence of Triphenylphosphine
831
˚
Table 1. Crystal data and structure refinement details for 8c.
Crystal data:
Table 2. Selected interatomic distances (A), valence angles
(deg) and torsion angles (deg) in 8c.
Empirical formula
C19H19NO4
325.35
O(1)–C(3)
O(2)–C(2)
O(2)–C(3)
O(3)–C(12)
O(4)–C(13)
N(1)–C(4)
1.2146(10) N(1)–C(12)
1.4554(9) N(1)–C(13)
1.3336(9) C(3)–C(4)
1.2133(9) C(4)–C(5)
1.2113(9) C(5)–C(6)
1.4278(9) C(17)–C(18)
1.3980(10)
1.4026(10)
1.4911(10)
1.3461(11)
1.4675(10)
1.3363(12)
Formula weight [g mol−1
]
Crystal system, space group
monoclinic, P21/c
10.004(3)
11.786(3)
14.197(3)
106.57(3)
1604.4(7)
4
1.347
0.095
688
˚
a [A]
˚
b [A]
˚
c [A]
β [deg]
C(12)–N(1)–C(4)
C(13)–N(1)–C(4)
C(12)–N(1)–C(13) 112.13(6) C(12)–C(15)–C(16) 110.30(6)
C(4)–C(5)–C(6) 131.77(7) C(14)–C(15)–C(16) 115.21(6)
C(13)–C(14)–C(15) 104.86(6) C(18)–C(17)–C(16) 120.08(7)
C(13)–C(14)–C(19) 110.70(6) C(17)–C(18)–C(19) 120.44(7)
122.48(6) C(19)–C(14)–C(15) 115.04(6)
122.43(6) C(12)–C(15)–C(14) 104.97(6)
3
˚
V [A ]
Z
Dcalc [g cm−3
]
µ [mm−1
]
F(000) [e]
Crystal size [mm3]
Crystal color and form
Data collection:
0.46×0.40×0.28
C(3)–O(2)–C(2)–C(1)
C(2)–O(2)–C(3)–C(4)
C(12)–N(1)–C(4)–C(5)
C(13)–N(1)–C(4)–C(5)
O(2)–C(3)–C(4)–C(5)
O(2)–C(3)–C(4)–N(1)
N(1)–C(4)–C(5)–C(6)
C(4)–C(5)–C(6)–C(7)
N(1)–C(12)–C(15)–C(16)
N(1)–C(13)–C(14)–C(19)
C(19)–C(14)–C(15)–C(12)
C(13)–C(14)–C(15)–C(16)
C(19)–C(14)–C(15)–C(16)
C(16)–C(17)–C(18)–C(19)
179.8(1)
176.1(1)
−93.2(1)
107.8(1)
−4.5(1)
177.3(1)
−0.2(2)
9.2(2)
−118.4(1)
121.2(1)
−123.6(1)
119.8(1)
−2.0(1)
−0.8(1)
colorless block
Diffractometer
Data collection method
Monochromator
Radiation type, λ [A]
T [K]
Kuma KM4CCD
ω scans
graphite
MoKα , 0.71073
100(2)
3.40 – 36.61
−16 ≤ h ≤ 13, −19 ≤ k ≤ 19,
−23 ≤ l ≤ 23
25999
˚
θ Range [deg]
h, k, l Ranges
Measured reflections
Independent reflections
Observed refl. [I ≥ 2σ(I)]
Completeness to θ = 30.00◦
Refinement:
7391
5775
0.991
Refinement on
F2
Data/restraints/parameters
7391/0/293
2
R [Fo ≤ 2σ(Fo2)]
R1 = 0.0420, wR2 = 0.1126
R1 = 0.0576, wR2 = 0.1179
1.070
R (all data)
GooF = S
Weighting parame−te3r a/b
0.0715/0.0362
0.56/−0.23
˚
∆ρmax/∆ρmin [e A
]
ꢀ
R1 = ΣꢀFo| − |Fcꢀ/Σ|Fo|; wR2 = Σ[w(Fo −Fc2)2]/Σ[w(Fo2)2];
2
Weighting scheme: w = 1/[σ2(Fo2)+(aP)2 +bP] where P = (Fo
2Fc2)/3.
+
2
ester group is in antiperiplanar conformation in re-
lation to the vinyl atom C(5). The short intramolecu-
lar contacts C(5)···O(2) and C(7)···N(1) may indicate
the presence of weak intramolecular hydrogen inter-
actions C(5)–H(5)···O(2) and C(7)–H(7)···N(1), giving
rise to five-membered S(5) and six-membered S(6) mo-
tifs, respectively. Both of them are formed in plane 1
and stabilize the molecular structure of 8c. It is to
note here, that a search of the Cambridge Structural
Database [9] revealed fourteen hits for compounds
of related structures, i. e. those bearing different sub-
stituents at nitrogen and different ester groups (usually
–C(O)OMe and –C(O)OEt), with most of them exist-
ing in the Z rather than E isomeric form (only two hits
for the latter). Most of the Z geometrical isomers also
show some deviations from the planarity of the frag-
Fig. 2. The centrosymmetric molecular dimer formed by
the adjacent molecules joined by C(14)–H(14)···O(1)iii and
C(15)–H(15)···O(1)iii hydrogen bonds (dashed lines). In-
tramolecular C(5)–H(5)···O(2) and C(7)–H(7)···N(1) close
contacts are shown with dotted lines. Symmetry codes are
as given in Table 3.
ment defined here as plane 1, usually the phenyl group
being slightly twisted. Most of the compounds, except
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A. T. Mahyari et al. · Addition of Imides to Ethyl 3-Phenyl-2-propynoate in the Presence of Triphenylphosphine
Table 3. Geometry of proposed hy-
˚
˚
˚
˚
D–H···A
D–H (A) H···A (A) D···A (A) D–H···A (deg) Offset (A)
drogen bonds and C–H···O/N/π close
C(1)–H(1C)···O(3)i
C(5)–H(5)···O(2)
0.99(2)
0.96(1)
0.96(1)
1.00(2)
0.97(1)
1.00(1)
0.99(1)
0.98(1)
0.99(1)
0.99(1)
2.56(2)
2.28(1)
2.52(1)
2.52(2)
2.64(1)
2.51(1)
2.42(1)
2.62(1)
2.73(1)
2.83(2)
3.424(2)
2.720(1)
3.398(1)
3.138(2)
3.514(2)
3.233(2)
3.202(2)
3.574(2)
3.541(2)
3.627(2)
147(1)
107(1)
151(1)
120(1)
150(1)
130(1)
135(1)
166(1)
140(1)
139(1)
–
–
˚
contacts for 8c (A, deg).
C(5)–H(5)···O(4)ii
C(7)–H(7)···N(1)
–
–
–
–
–
–
0.21
0.13
i
Symmetry codes: −x + 1, y − 1/2, −z +
3/2; ii −x+1, −y+1, −z+1; iii −x, −y+
1, −z+1; iv x, −y+3/2, z−1/2. Cg(1) is
the centroid of the phenyl ring [C(6)–C(7)–
C(8)–C(9)–C(10)–C(11)].
C(11)–H(11)···O(4)ii
C(14)–H(14)···O(1)iii
C(15)–H(15)···O(1)iii
C(19)–H(19A)···O(3)iv
C(2)–H(2A)···Cg(1)ii
C(2)–H(2B)···Cg(1)i
Fig. 3. The arrangement of the
molecules within the ribbons paral-
lel to a axis. Intermolecular C–H···O
contacts are shown with dashed lines,
and intramolecular C–H···O/N and in-
termolecular C–H···π contacts – with
dotted lines. Symmetry codes are as
given in Table 3.
for two metal complexes, also have the carbonyl O
Adjacent, symmetry-related dimers are joined to
atom oriented antiperiplanarly in relation to the vinylic each other by the hydrogen contacts of C–H···O
C–H bond. Short C···O and C···N intramolecular con- and C–H···π-type, the geometrical parameters of
tacts, similar to that observed in 8c, may also be found which are given in Table 3. First of all, adjacent
in the compounds described so far, usually in those of dimers arranged along the a axis are linked by
them, which were shown to have the fragment defined centrosymmetric three-centered, bifurcated contacts:
as plane 1 close to planar.
C(5)–H(5)···O(4)ii, C(11)–H(11)···O(4)ii (dashed lines
in Figs. 3 and 4) and by centrosymmetric C(2)–
H(2A)···π[Cg(1)ii] interactions (shown with dotted
lines). That gives rise to ribbons parallel to the a
axis (see Fig. 3). Every ribbon is joined to four
adjacent ones by the interactions of C–H···O and
C–H···π-type: bifurcated C(1)–H(1C)···O(3)i, C(19)–
H(19A)···O(3)iv contacts and C(2)–H(2B)···π[Cg(1)i]
interactions, which is easy to see in Fig. 4. The com-
bination of all these C–H···O, C–H···N and C–H···π
interactions observed in the crystal of compound 8c
results in a three-dimensional network of hydrogen
bonds.
The overall geometry of the tetrahydrophthalim-
ide moiety in 8c is identical to that observed in free
tetrahydrophthalimide [10]. Atoms H(14) and H(15)
at the fused five-membered ring and the partially hy-
drogenated six-membered ring junction have a mutual
cis orientation. Cremer & Pople [11] puckering pa-
˚
rameters for the cyclohexene ring of Q = 0.555(1) A,
Θ = 89.3(1)◦ and Φ = 301.7(1)◦ indicate a boat
conformation. The dihedral angles between the least-
squares plane through the atoms C(14)/C(15)/C(16)/
C(19) and the planes defined by C(16)/C(17)/C(18)/
C(19) and N(1)/C(12)/C(13)/C(14)/C(15) are 41.8(1)◦
and 60.3(1)◦, respectively.
Atoms C(14) and C(15) of every two adjacent
molecules are involved in bifurcated, three-centered
C(14)–H(14)···O(1)iii and C(15)–H(15)···O(1)iii hy-
Conclusions
In conclusion, we have developed a convenient, one-
drogen bonds. That gives rise to centrosymmetric pot regio- and stereoselective method for preparing
molecular dimers as it is shown in Fig. 2.
sterically congested N-vinyl imides (8a– c) utilizing
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A. T. Mahyari et al. · Addition of Imides to Ethyl 3-Phenyl-2-propynoate in the Presence of Triphenylphosphine
833
dichloromethane (5 mL) was added dropwise a mixture of
ethyl 3-phenyl-2-propynoate (0.17 mL, 1 mmol) in dichloro-
◦
methane (2 mL) at −10 C over 15 min. The mixture was
allowed to warm up to r. t. and stirred for 48 h at r. t. The
solvent was removed under reduced pressure and the viscous
residue was purified by flash column chromatography (silica
gel; petroleum ether-ethyl acetate). The solvent was removed
under reduced pressure to leave the product as a light yellow
oil. Yield: 0.286 g (97 %). – IR (neat): ν = 2984, 1723, 1653,
1407, 1269 cm−1. – 1H NMR (CDCl3): δ = 1.31 (t, 3H, 3J =
7.0 Hz, CH3), 2.73 – 2.87 (2 m, 2H, 2 CH3), 4.25 (q, 2H,
3J =7.0 Hz, OCH2), 7.33 (m, 5H, arom), 8.02 (s, 1H, =CH). –
13C NMR (CDCl3): δ = 14.14 (CH3), 28.72 (2 CH2), 62.10
(OCH2), 121.07 (=CH), 128.94, 129.00 and 130.54 (5 CH),
132.13 and 142.10 (2C), 162.73 (C=O ester), 175.74 (2 C=O
of imide). – C15H15NO4 (273.29): calcd. C 65.93, H 5.53,
N 5.13; found C 65.75, H 5.40, N 5.04.
Selected data for ethyl (Z)-2-(1,3-dioxo-1,3-dihydro-2H-
isoindol-2-yl)-3-phenyl-2-propenoate 8b: White crystals.
Yield: 0.31 g (97 %); m. p. 104.0 – 108.0 ◦C. – IR (KBr):
ν = 2930, 1715, 1653, 1407, 1276 cm−1. – 1H NMR
(CDCl3): δ = 1.28 (t, 3H,3J = 7.0 Hz, CH3), 4.27 (q,
2H,3J = 7.0 Hz, OCH2), 7.22 – 4.40 (m, 5H, arom), 7.74 –
7.91 (m, 4H, arom), 8.10 (s, 1H, =CH). – 13C NMR (CDCl3):
δ = 14.17 (CH3), 62.04 (OCH2), 120.39 (=CH), 123.99,
128.92, 129.38, 130.52 and 134.50 (9CH), 132.13, 132.39
and 142.72 (4C), 163.36 (C=O of ester), 169.86 (2 C=O
of imide). – C19H15NO4 (321.33): calcd. C 71.02, H 4.70,
N 4.36; found C 71.13, H 4.64, N 4.29.
Fig. 4. The arrangement of the adjacent ribbons in the crystal
lattice of 8c, viewed down the ribbon and the a axis. Inter-
molecular C–H···O contacts are shown with dashed lines,
and intramolecular C–H···O/N and intermolecular C–H···π
contacts with dotted lines. Symmetry codes are given in Ta-
ble 3.
Selected data for ethyl 2-(1,3-dioxo-1,3,3a,4,7,7a-hexa-
hydro-2H-isoindol-2-yl)-3-phenyl-2-propenoate 8c: Color-
less crystals. Yield: 0.32 g (97 %); m. p. 96.0 – 100.0 ◦C. – IR
(KBr): ν = 2953, 1715, 1661, 1407, 1269 cm−1. – 1H NMR
(CDCl3, %E = 33 and %Z = 67) for Z: δ = 1.31 (t, 3H,
the in situ generation of the phosphonium salts. Other
aspects of this process are under investigation. The
X-ray structure of 8c (in its Z isomeric form) revealed
that in the solid state the tetrahydrophthalimide moiety
exists in a boat conformation and is almost perpendic- 3J = 7.0 Hz, CH3), 2.28 and 2.63 (2m, 4H, 2 CH2), 3.12 and
3.27 (2m, 2H, 2 CH), 4.26 (q, 2H,3J = 7.0 Hz, OCH2), 5.95
ular to the plane defined by the remaining atoms of the
molecule. The crystal structure of 8c is stabilized by
extensive C–H···O/N/π interactions.
(m, 2H, HC=CH), 7.31 (m, 5H, arom), 7.98 (s, 1H, =CH). –
13C NMR (CDCl3) for Z: δ = 14.15 (CH3), 23.34 (2CH2),
39.70 (2CH), 62.03 (OCH2), 120.99 (=CH), 127.23, 128.19,
128,61 and 129.66 (7CH), 131.93 and 142.10 (2C), 162.77
(C=O of ester), 178.60 (2C=O of imide). – 1H NMR (CDCl3,
E : Z = 33 : 67) for E: δ = 1.25 (t, 3H, 3J = 7 Hz, CH3), 2.22
and 2.58 (2 m, 4H, 2CH2), 3.13 and 3.26 (2m, 2H, 2CH),
4.19 (q, 2H, 3J = 7 Hz, OCH2), 5.91 (m, 2H, HC=CH), 7.24
(s, 1H, =CH), 7.30 (s, 5H, arom). – 13C NMR (CDCl3) for
E: δ = 23.09 (2CH2), 39.51 (2CH), 62.92 (OCH2), 121.40
(=CH), 127.23, 128.85, 128.97 and 130.40 (7CH), 132.38
and 141.93 (2C), 162.77 (C=O of ester), 178.6 (2C=O of
imide). – C19H19NO4 (325.36): calcd. C 70.14, H 5.89,
N 4.30; found C 70.31, H 5.99, N 4.21.
Experimental Section
Melting points were measured on an Electrothermal 9100
apparatus and are uncorrected. Elemental analyses were per-
formed using a Heraeus CHN-O-Rapid analyzer. IR spectra
1
were recorded on a Shimadzu IR-460 spectrometer. H and
13C NMR spectra were measured with a Bruker Spectrospin
spectrometer at 250 and 62.5 MHz, respectively.
Preparation of ethyl (Z)-2-(2,5-dioxo-2,5-dihydro-1-pyrrol-
1-yl)-3-phenyl-2-propenoate (8a).
General procedure
Preparation of single crystals of ethyl (Z)-2-(1,3-di-
To a magnetically stirred solution of triphenylphosphine oxo-1,3,3a,4,7,7a-hexahydro-2H-isoindol-2-yl)-3-phenyl-2-
(0.262 g, 1 mmol) and succinimide (0.099 g, 1 mmol) in propenoate 8c: Single crystals of the title compound were
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A. T. Mahyari et al. · Addition of Imides to Ethyl 3-Phenyl-2-propynoate in the Presence of Triphenylphosphine
prepared using the branch tube method [12] with light by full-matrix least-squares techniques with anisotropic ther-
◦
petroleum ether at 60 C during 24 h. The colorless crystals mal parameters for non-H atoms using SHELXL-97 [15]. All
were filtered off, washed with cold light petroleum ether H atoms were found in difference Fourier maps and were re-
(3 mL) and dried at r. t.
fined isotropically. All figures were made using the program
XP [16]. Cremer & Pople [11] puckering parameters were
calculated using the program PLATON [17].
Crystal structure determination of 8c
The crystallographic measurement was performed on a
κ-geometry Kuma KM4CCD automated four-circle diffrac-
tometer with graphite-monochromatized MoKα radiation.
The data for the crystal were collected at 100(2) K using the
Oxford Cryosystems cooler. A summary of the conditions
for the data collection and the structure refinement parame-
ters are given in Table 1. The data were corrected for Lorentz
and polarization effects. Data collection, cell refinement,
and data reduction and analysis were carried out with the
KM4CCD software (Oxford Diffraction Poland): CrysAlis
CCD and CrysAlis RED, respectively [13]. The structure was
solved by Direct Methods using SHELXS-97 [14] and refined
Supplementary material
CCDC 635253 contains the supplementary crystallo-
graphic data for this paper. These data can be obtained free
of charge from The Cambridge Crystallographic Data Centre
via www.ccdc.cam.ac.uk/data request/cif.
Acknowledgement
The Iranian authors are thankful to the Research Council
of the Zanjan Islamic Azad University for partial support of
this work.
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Unauthenticated
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