Cobalt (II) and copper (I) complexes of rigid bidentate [N-(2, 6-diisopropyl-phenyl)imino]acenapthenone ligand: Synthesis and structural studies

Article abstract of DOI:10.1002/zaac.201200189

The cobalt(II) complex [CoCl₂(2, 6-iPrC₆H ₃-BIAO)]₂ (1) of rigid unsymmetrical imine, carbonyl mixed ligand [N-(2, 6-diisopropylphenyl)-imino]acenapthenone] (2, 6-iPrC ₆H₃-BIAO) (L1) can be achieved by the reaction of CoCl₂ and neutral [N-(2, 6-diisopropylphenyl)-imino]acenapthenone] ligand. When ligand L1 reacted with CuCl in dichloromethane solution, only nitrogen coordinated copper complex [CuCl(2, 6-iPrC₆H ₃-BIAO)] (2) was obtained. In the solid-state structure, compound 1 is dimeric through the chelating two μ₂ chlorine atoms and each cobalt atom adopts either a distorted trigonal bipyramidal or a distorted square pyramidal arrangement. In contrast, the molecular structure of compound 2 reveals that copper is coordinated by imino nitrogen and adopts a linear arrangement around the central metal atom. The crystal structure of the rigid bidentate mixed nitrogen and oxygen ligand (2, 6-iPrC₆H ₃-BIAO) (L1) is also reported. Copyright

Full text of DOI:10.1002/zaac.201200189

ARTICLE
DOI: 10.1002/zaac.201200189
Cobalt (II) and Copper (I) Complexes of Rigid Bidentate [N-(2,6-
Diisopropyl-phenyl)imino]acenapthenone Ligand: Synthesis and Structural
Studies
Srinivas Anga,[a] Mitali Paul,[a] Kishor Naktode,[a] Ravi K. Kottalanka,[a] and
Tarun K. Panda*[a]
Keywords: Acenapthenone; Cobalt; Copper; Metallacycles; Chelating ligands; Steric crowding
Abstract. The cobalt(II) complex [CoCl2(2,6-iPrC6H3-BIAO)]2 (1) of state structure, compound 1 is dimeric through the chelating two μ2
rigid unsymmetrical imine, carbonyl mixed ligand [N-(2,6-diisoprop- chlorine atoms and each cobalt atom adopts either a distorted trigonal
ylphenyl)-imino]acenapthenone] (2,6-iPrC6H3-BIAO) (L1) can be bipyramidal or a distorted square pyramidal arrangement. In contrast,
achieved by the reaction of CoCl2 and neutral [N-(2,6-diisoprop- the molecular structure of compound 2 reveals that copper is coordi-
ylphenyl)-imino]acenapthenone] ligand. When ligand L1 reacted with
CuCl in dichloromethane solution, only nitrogen coordinated copper
complex [CuCl(2,6-iPrC6H3-BIAO)] (2) was obtained. In the solid-
nated by imino nitrogen and adopts a linear arrangement around the
central metal atom. The crystal structure of the rigid bidentate mixed
nitrogen and oxygen ligand (2,6-iPrC6H3-BIAO) (L1) is also reported.
presence of one exocyclic carbonyl group in place of second
exocyclic imine group, the σ-donating and π-accepting capa-
bilities will be reduced in comparison with (Ar-BIAN) ligand.
The absence of the second 2,6-diisopropylphenyl group also
significantly decrease the steric bulk. Thus it is very interesting
to see how the moderate difference in electronic and steric
environment will impact on the central metal atom like cobalt
and copper and subsequent effect on catalytic behavior.
Introduction
In the post metallocene era, chelating nitrogen ligands with
bulky substituents are being explored as alternatives to η5-cy-
clopentadienyl ligands for the design of olefin polymerization
catalysts based on early and late transition metal complexes.[1–
6]
The use of bidentate and tridentate ligands received signifi-
cant attention by many research groups due to their wide appli-
cation as auxiliary ligands in catalysis.[7–11] To improve the
catalytic activity of the metal complexes, proper ligand design
is most important. Very recently, the rigid bidentate nitrogen
based di-imine ligand bis(N-arylimino)acenaphthene (Ar-
BIAN), which was first introduced by van Asselt and Elsevier
in the early 1990s,[12] was used in various catalytic processes
in transition metal chemistry .[13–17] The presence of two exo-
cyclic imines to the heteroaromatic ring system lead to better Scheme 1. Synthesis of (Ar-BIAO, L1) and (Ar-BIAN).
σ-donating and better π-accepting properties than that of 2,2Ј-
Herein we present the synthesis and structural studies of two
bipyridine and 1,10-phenanthroline ligands.[18–20] In addition,
transition metal complexes of cobalt(II) and copper(I) with Ar-
the rigid acenaphthene backbone prevents rotation around the
BIAO ligand, [CoCl2(2,6-iPrC6H3-BIAO)]2 (1) and CuCl(2,6-
iPrC6H3-BIAO) (2). In addition we report the solid-state struc-
ture of the ligand Ar-BIAO.
imine carbon–carbon bond and forces the imine nitrogen atoms
to remain in a fixed cis orientation, favoring chelating coordi-
nation to a central metal atom.[18] Considering the rigid un-
symmetrical imine, carbonyl mixed ligand [N-(2,6-diisoprop-
ylphenyl)-imino]acenapthenone (Ar-BIAO, L1), which can be
obtained as the major product by the single condensation of
amine to one of the carbonyl group (Scheme 1)[20] of the acen-
Results and Discussion
Ligand
aphthenequinone, the situation is quite different. Due to the
The ligand L1 was prepared according to a literature pro-
* Prof. Dr. T. K. Panda
cedure[20a] and the spectroscopic data are in accordance with
Fax: + 91-40-23016032
the reported values. The solid-state structure of compound L1
was established by single crystal X-ray diffraction analysis.
Compound L1 crystallizes in the orthorhombic space group
P212121 having four molecules and a molecule of dichloro-
E-Mail: tpanda@iith.ac.in
[a] Department of Chemistry
Indian Institute of Technology Hyderabad
Ordnance Factory Estate
Yeddumailaram 502205, Andhra Pradesh, India
Z. Anorg. Allg. Chem. 2012, 638, (9), 1311–1315
© 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
1311

T. K. Panda et al.
ARTICLE
methane in the unit cell. The molecular structure of compound
L1 is shown in Figure 1. In compound L1, the C–O bond
length of 1.220(4) Å is within the range of typical carbonyl
C=O bond, the C–N bond length of 1.282(4) Å is in the range
of imines bond lengths and the C1–C2 bond length is
1.539(5) Å and shows a C–C single bond. In the similar com-
pounds (3,5-xylyl-BIAO), (4-Cl-BIAO), and (2,6-xylyl-BIAO)
reported by Jones and co-workers, similar N–C bond lengths
[1.2763(14), 1.2742(15), and 1.2777(9) Å, respectively] and
similar C–O bond lengths [1.2217(13), 1.2131(14), and
1.2149(9) Å, respectively] are observed.[22c] The carbonyl car-
bon as well as the imine carbon atoms are sp2 hybridized and
coplanar with the acenapthene moity. The plane containing the
acenapthene moity and oxygen and nitrogen makes a dihedral
angle of 79.69° with the phenyl ring plane attached to the im-
ine nitrogen atom. The deviation of the dihedral angle from
the orthogonal arrangement of the two planes are observed and
can be attributed due to steric crowding of the ligand.
Scheme 2. Synthesis of cobalt and copper complex of L1.
The cobalt complex 1 is paramagnetic, which makes it in-
1
adequate for H and 13C{1H} NMR studies. The melting point
of compound 1 is 175 °C. In the FT-IR spectrum, compound 1
shows a similar absorption to the ligand L1 and no significant
observation can be obtained. The solid-state structure of com-
pound 1 was solved by X-ray diffraction analysis and the struc-
tural parameters are given in Table 1. Compound 1 crystallizes
in the monoclinic space group P21/n with two molecules in the
unit cell. One dichloromethane solvent molecule is also present
in the asymmetric unit. The cobalt complex is dimeric and two
cobalt atoms are bridged by two chlorine atoms (Figure 2).
The cobalt complex is centrosymmetric due the presence of an
inversion center. Two five membered metallacycles Co1–O1–
C2–C1–N1 and Co1i–O1i–C2i–C1i–N1i are formed by the two
ligand moieties and two cobalt atoms. Each cobalt atom is lig-
ated through the lone pairs on neutral carbonyl oxygen and the
imine nitrogen atoms. The arrangement around each cobalt
atom is best described either as distorted square pyramidal
having N1, O1, Cl1, Cl1i atoms in the basal position and Cl2
in the axial position or as distorted trigonal bipyramidal having
N1, Cl1, Cl2 atoms are in the equatorial position and O1, Cl1i
atoms are in the axial position. The Co–O distance is
2.382(4) Å, which is in good agreement with the cobalt oxygen
coordination bond rather than a covalent bond [Co–O
2.095(2) Å for covalent bond[21]] and the Co(1)–N(1) distance
(2.062(5) Å) is in the range of other cobalt nitrogen coordina-
tion bonds since similar Co–N distances are observed for
Figure 1. Solid state structure of compound L1. Selected bond
lengths /Å and bond angles /° are given: O(1)–C(2) 1.220(4), N(1)–
C(1) 1.282(4), N(1)–C(13) 1.427(4), C(1)–C(2) 1.539(5), C(1)–N(1)–
C(13) 120.7(3), N(1)–C(1)–C(11) 133.7(3), N(1)–C(1)–C(2) 119.8(3),
O(1)–C(2)–C(3) 128.5(4), O(1)–C(2)–C(1) 125.2(3).
Metal Complexes
To a suspension of cobalt (II) chloride in dichloromethane, DippDADCoCl2 (2.050(3) Å, DippDAD = 2,6 diisopropyl 1,4-
a solution of ligand L1 was added dropwise in a 1:1 molar diaza-1,3-butadiene) and CoCl2(2.4.6-Me3C6H2(BIAN)
ratio, an immediate color change from blue to brown was no- (2.0753(12) Å).[22] The three different Co–Cl distances
ticed. The reaction mixture was stirred overnight at room tem- [2.3012(17), 2.4106(15), Co(1)–Cl(2)
Co(1)–Cl(1)i
perature for further 12 h. The reaction solution was filtered in 2.2277(18) Å] point to an asymmetric attachment of the chlo-
an inert atmosphere and the filtrate was evaporated under re- rine atoms to the cobalt atoms. One chlorine (Cl2) atom is
duced pressure. The solid residue was washed with dry petro- purely covalently bonded, whereas Cl1 is bonded covalently
leum ether. The title compound [CoCl2(2,6-iPrC6H3-BIAO)]2 as well as in a bridging mode with an elongated Co–Cl dis-
(1) was recrystallized from dichloromethane (Scheme 2). In a tance of 2.3012(17) Å, the third chlorine atom Cl(1i) is coordi-
similar fashion the copper complex CuCl(2,6-iPrC6H3-BIAO) natively bonded with a Co–Cl distance of 2.4106(15) Å. A
(2) was obtained by the reaction of copper(I) chloride with Ar- similar situation is observed for the second cobalt atom as
BIAO in dichloromethane solution (Scheme 2). The diamag- well. Only the C–O [1.228(7) vs. 1.214(8) Å], and the C–N
netic complex 2 was characterized by spectroscopic techniques bond lengths [1.292(7) vs. 1.288(8) Å], in compound 1 are un-
and combustion analysis. The solid-state structures of both the perturbed due to the higher electronegativity of oxygen and
complexes were established by single crystal X-ray diffraction nitrogen, the C1–C2 bond lengths [1.512(8) vs. 1.556(9) Å]
analysis.
are slightly shorter due to chelation with cobalt compared to
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© 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Z. Anorg. Allg. Chem. 2012, 1311–1315

Cobalt (II) and Copper (I) Complexes of Rigid Bidentate [N-(2,6-Diisopropyl-phenyl)imino]acenapthenone Ligand
Table 1. Crystallographic details of (2,6-iPrC6H3-BIAO) (L1), [CoCl2(2,6-iPrC6H3-BIAO)]2 (1) and [CuCl(2,6-iPrC6H3-BIAO)] (2).a).
L1·(CH2Cl2)
1·(CH2Cl2)
2
Formula
Formula weight
Space group
a /Å
b /Å
c /Å
C25H25Cl2NO
426.36
P212121
9.5786(5)
15.0627(8)
15.6115(9)
C50H50Cl8Co2N2O2
1112.38
P21/n
11.9988(17)
13.209(2)
16.561(3)
95.312(14)
2613.5(7)
2
C24H23ClCuNO
440.43
P21/n
10.6867(15)
13.0589(12)
15.6764(18)
107.827
2082.7(4)
4
β /°
V /Å3
2252.4(2)
4
1.257
Z
Density /mg·m–3
T /K
1.414
150(2)
1.405
150(2)
150(2)
Radiation
Mo-Kα
Cu-Kα
Cu-Kα
(λ = 0.71073 Å)
0.304
(λ = 1.54184 Å)
9.045
(λ = 1.54182 Å)
2.758
μ /mm–1
Absorption correction
Reflections collected
Unique reflections
Observed reflections
R1; wR2
Empirical
5918
3699 [Rint = 0.0385]
3699
Empirical
9472
4956 [Rint = 0.0497]
4956
Empirical
7292
3576[Rint = 0.0418]
3576
0.0575; 0.1554
0.0859; 0.02621
0.0450; 0.1154
a) Programs used: SHELXS-97[23] and SHELXL-97[24]
.
the bond length in the ligand L1. The distance between two absorption at 1655 cm–1 can be assigned for C=N bond stretch-
1
cobalt atoms is 3.334 Å, which suggests no interaction be-
tween the atoms. Each cobalt atom is placed 0.414 Å above
the plane containing acenapthene and the donor oxygen and
nitrogen atoms. The dihedral angle between the acenapthene
plane and the plane containing the nitrogen, oxygen, and cobalt
atoms is 13.62°. However, the phenyl rings on the nitrogen
atoms have a dihedral angle of 82.70° with the acenapthene
plane containing nitrogen and oxygen atoms as well.
ing. In the H NMR spectrum of the diamagnetic compound
2, two doublet signals at δ = 0.82 ppm and 1.16 ppm in 1:1
ratio are obtained. They can be assigned as the methyl protons
attached to isopropyl groups on the aromatic ring. The septet
signal at δ = 2.91 ppm, which is slightly downfield shifted
compared to that of L, corresponds to the resonance of the CH
proton present in the isopropyl groups. The resonance of the
protons attached to the acenapthene moiety and the phenyl ring
are in the expected regions. In the 13C{1H} NMR spectrum of
compound 2, the carbonyl carbon is mostly deshielded and
appears at δ = 187.2 ppm, further the signals of the imine car-
bon atom at δ = 161.3 ppm, and the phenyl carbon attached to
nitrogen atom at δ = 142.5 ppm, which is slightly highfield
shifted upon coordination with copper, are observed.
The molecular structure of the copper complex 2 was solved
by single-crystal X-ray diffraction analysis and the structural
parameters are given in Table 1. In the solid state, compound
2 crystallizes in the monoclinic space group P21/n with four
molecules in the unit cell. The CuI atom is coordinated by one
imine nitrogen atom and one chloride ion to adopt a linear
arrangement. The Cu–N1 bond length of 1.900(3) Å is in the
range of Cu–N coordination bond. The angle formed by the
chlorine, copper, and nitrogen atoms, N1–Cu–Cl1, is
173.64(9)° which indicates almost linear arrangement of the
copper atom. The non coordination of the oxygen atom to the
copper atom can be attributed by the higher electronegativity
of oxygen and lower positive charge over copper, which pre-
vents any interaction between copper and oxygen atoms. The
C2–O1 distance [1.220(4) vs. 1.214(8) Å] remains almost un-
changed to that in the ligand L1. The copper atom is in the
same plane containing acenapthene and the donor atom nitro-
gen, but the oxygen is 0.127 Å above the plane. This plane
also has a dihedral angle of 79.09° to the plane containing the
Figure 2. Solid-state structure of 1 showing the atom labeling scheme,
hydrogen atoms are omitted for clarity. Selected distances /Å and
angles /°: Co(1)–N(1) 2.062(5), Co(1)–Cl(2) 2.2277(18), Co(1)–Cl(1)
2.3012(17), Co(1)–O(1) 2.382(4), Co(1)–Cl(1i) 2.4106(15), Cl(1)–
Co(1i) 2.4106(15), O(1)–C(2) 1.228(7), N(1)–C(1), 1.292(7), N(1)–
C(13) Cl(3)–C(25) 1.667(10), Cl(4)–C(25) 1.798(12). N(1)–Co(1)–
Cl(2) 109.53(15), N(1)–Co(1)–Cl(1) 127.46(15), Cl(2)–Co(1)–Cl(1)
118.46(7), N(1)–Co(1)–O(1) 76.04(16), Cl(2)–Co(1)–O(1) 86.01(12),
Cl(1)–Co(1)–O(1) 86.83(12), N(1)–Co(1)–Cl(1i) 97.59(13), Cl(2)–
Co(1)–Cl(1i) 104.94(7), Cl(1)–Co(1)–Cl(1i) 89.95(6), O(1)–Co(1)–
Cl(1i) 168.78(12), Co(1)–Cl(1)–Co(1i) 90.05(6), C(2)–O(1)–Co(1)
106.2(4), C(1)–N(1)–C(13) 118.2(5), C(1)–N(1)–Co(1) 116.7(4),
C(13)–N(1)–Co(1) 124.1(3).
In the FT-IR spectrum of compound 2 a strong absorption
at 1724 cm–1 for the C=O stretching can be observed, and the phenyl ring on the imine nitrogen atom (Figure 3).
Z. Anorg. Allg. Chem. 2012, 1311–1315
© 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
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1313

T. K. Panda et al.
ARTICLE
CoCl2(Ar-BIAO)(CH2Cl2) (1): A blue suspension of CoCl2 (52 mg,
0.41 mmol) in CH2Cl2 (5 mL) was treated with a red solution of [(2,6-
diisopropylphenyl)imino]acenapthenone (140 mg, 0.41 mmol) in
CH2Cl2 (5 mL). The reaction mixture turned to brown color and it was
stirred overnight. The reaction mixture was filtered and the solvent
was evaporated to dryness. The brown solid residue was washed with
petroleum ether and finally re-crystallized from CH2Cl2. Yield: 30%
(68 mg), M.p. 175 °C. C50H50Cl8Co2N2O2 (1112.38): calcd. C 53.96,
H 4.53, N 2.52%; found, C 53.56, H 4.34, N 2.22%.
CuCl(Ar-BIAO) (2): To a stirred solution of CuCl (50 mg, 0.5 mmol)
in CH2Cl2 (2 mL) was added ligand L1 (172 mg, 0.5 mmol) in CH2Cl2
(3 mL). The reaction mixture was kept stirring overnight, and finally
filtered. The solvent was evaporated from the clear solution under high
vacuum to give a red colored powder. The compound was re-crys-
tallized from CH2Cl2 at –4 °C. Yield is 65.6% (145 mg), M.p. 170 °C.
C24H23ClCuNO (440.43): calcd. C 65.43, H 5.27, N 3.18%; found C
65.17, H 5.15, N 3.22%. FT-IR: ν˜ = 3056, 2960, 1724, 1655, 1587,
Figure 3. Solid-state structure of 2 showing the atom labeling scheme.
Selected distances /Å and angles /°: Cu–Cl 2.1099(10), Cu–N1
1.900(3), N1–C1 1.281(4), N1–C13 1.451(4), O1–C2 1.220(4); N1–
Cu–Cl1 173.64(9), C1–N1–C13 118.8(3), C1–N1–Cu 122.3 (2), C1–
C2–O1 123.2(3), C11–C1–C2 107.1(3).
1
1258, 1017, 795, 779 cm–1. H NMR (CDCl3, 400 MHz): δ = 8.22–
8.30 (m, 2 H, ArH), 8.07–8.09 (d, 1 H, J = 8.00 Hz, ArH), 7.84–7.87(t,
1 H, J = 8.00 Hz, ArH), 7.35–7.43 (m, 3 H, ArH), 7.17–7.18(d, 1 H,
J = 4.00 Hz ArH), 6.68–6.69(t, 1 H, J = 1.2 Hz), 2.90–2.91 (m, 2 H,
CHMe2), 1.15–18(d, 6 H, J = 12.00 Hz, CHMe2), 0.82(br.,s, 6 H,
CHMe2) ppm. 13C{1H} NMR (CDCl3, 100 MHz): δ = 187.2 (C=O),
161.3 (C=N), 142.5, 131.7, 131.5, 130.3, 129.0, 127.6, 122.6, 122.5,
122.4, 121.8, 30.2, 28.8, 27.2, 23.0, 22.8 ppm.
Conclusions
Cobalt and copper complexes with the rigid unsymmetrical
imine, carbonyl mixed ligand [N-(2,6-diisopropylphenyl)-imi-
no]acenapthenone] (L1) were prepared. Both complexes are
potentially active for polymerization of ethylene and further
studies are in progress.
X-ray Crystallographic Analyses: Single crystals of compound L1,
1, and 2 were grown from a solution of CH2Cl2 in an argon atmosphere
at a temperature of –4 °C. In each case a crystal of suitable dimensions
was mounted on a CryoLoop (Hampton Research Corp.) with a layer
of light mineral oil and placed in a nitrogen stream at 150(2) K. All
measurements were made with a Oxford Supernova X-calibur Eos
CCD detector with graphite-monochromatic Cu-Kα (1.54184 Å) or
Mo-Kα (0.71073 Å) radiation. Crystal data and structure refinement
parameters are summarized in the Table 1. The structures were solved
by direct methods (SIR92)[23] and refined on F2 by full-matrix least-
squares methods; using SHELXL-97.[24] Non-hydrogen atoms were
anisotropically refined. Hydrogen atoms were included in the refine-
ment on calculated positions riding on their carrier atoms. The function
Experimental Section
General: All manipulations involving air- and moisture-sensitive orga-
nometallic compounds were carried out in a argon atmosphere using
the standard Schlenk technique or argon-filled glove box. Dichloro-
methane and petroleum ether were dried with P2O5 followed by distil-
lation and kept under molecular sieves prior to use. 1H NMR
(400 MHz) and 13C{1H} NMR (100 MHz) spectra were recorded with
a BRUKER AVANCE III-400 spectrometer. BRUKER ALPHA FT-IR
was used for FT-IR measurement. HRMS was measured with an Ag-
ilent Technology Q-TOF instrument. Elemental analyses were per-
formed with a BRUKER EURO EA at the Indian Institute of Technol-
ogy Hyderabad. CoCl2 and CuCl were purchased from Sigma Aldrich
and used as such.
minimized was [Σw(Fo – Fc ) ] (w = 1 / [σ2 (Fo ) + (aP)2 + bP]),
2
2 2
2
2
where P = [Max(Fo2,0) + 2Fc2] / 3 with σ2(Fo ) from counting statis-
tics. The function R1 and wR2 were (Σ||Fo| – |Fc||) / Σ|Fo| and [Σw(Fo
Fc ) / Σ(wFo4)]1/2, respectively. The ORTEP-3 program was used to
2
–
2 2
draw the molecule.
Synthesis of [N-(2,6-Diisopropylphenyl)imino]-acenaphthenone
(L1)[20a]: Acenaphthenequinone (1 g, 5.48 mmol) and Na2SO4 (5 g)
were stirred at 45 °C in methanol (100 mL). 2,6-Diisopropylaniline
(0.97 g, 5.48 mmol) and acetic acid (0.60 mL) in methanol (100 mL)
were added dropwise to the acenaphthenequinone solution for 2 h.
After 10 h, the solvent was removed by a rotary evaporator. The crude
product was purified by column chromatography (hexane, silica gel)
to afford a red-orange solid. The compound was re-crystallized from
dichloromethane. Yield: 80%. M.p. 180 °C. 1H NMR (400 MHz,
CDCl3): δ = 8.13 (d, 2 H, An H), 7.9 (d, 1 H, An H), 7.77 (t, 1 H, An
H), 7.35 (t, 1 H, An H), 7.18 (m, 3 H, Ar H), 6.5 (d, 1 H, An H), 2.8
[sept, 2 H, CH(CH3)2], 1.1, 0.8 [2d, 12 H, CH(CH3)2] ppm. 13C NMR
(100 MHz, CDCl3, selected resonances): δ = 189.5 (C=O), 160.4
(C=N), 146.5, 143.0, 135.2, 132.1, 131.0, 130.0, 129.3, 128.3, 128.1,
127.7, 125.0, 123.5, 123.3, 122.2, 28.4 [CH(CH3)2], 23.4 [CH(CH3)2.
Crystallographic data (excluding structure factors) for the structures in
this paper have been deposited with the Cambridge Crystallographic
Data Centre, CCDC, 12 Union Road, Cambridge CB21EZ, UK. Copies
of the data can be obtained free of charge on quoting the depository
numbers CCDC-876799 (L1), CCDC-876797 (1), and CCDC-876798
(2) (Fax: +44-1223-336-033; E-Mail: deposit@ccdc.cam.ac.uk,
http://www.ccdc.cam.ac.uk).
Acknowledgements
This work was supported by the Department of Science and Technol-
ogy India (DST) under the SERC fast-trak Scheme (SR/FT/CS-74/
2010). S.A. thanks to CSIR, K.N. and R.K. thanks UGC, India for
HRMS: calcd. for C24H23NO (Mw: 341.18), [M + H]+ calculated their PhD fellowship. Generous supports from K. Mashima of Osaka
342.1813.
University, Japan are gratefully acknowledged.
1314
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© 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Z. Anorg. Allg. Chem. 2012, 1311–1315

Cobalt (II) and Copper (I) Complexes of Rigid Bidentate [N-(2,6-Diisopropyl-phenyl)imino]acenapthenone Ligand
[16] J. H. Groen, M. J. M. Vlaar, P. W. N. M. van Leeuwen, K. Vrieze,
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Received: April 23, 2012
Published Online: July 10, 2012
Z. Anorg. Allg. Chem. 2012, 1311–1315
© 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
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