¨
480
Unver and Durlu
Experimental
C34H22N2O2Cl2Cu; C, 77.42; H, 4.84; N, 11.29
(all values are given as percentages). Crystals suit-
able for X-ray diffraction were obtained by slow
evaporation from a saturated ethanol solution.
Synthesis of 1
N-(2-chloro)-naphthaldimine was prepared
by condensation of naphthaldehyde (0.861 g,
0.005 mol) and 2-chloroaniline (0.638 g,
0.005 mol) in 100 mL of ethanol. The reac-
tion mixture was stirred for 4 h and then placed
in a freezer for 18 h. The yellow precipitate
was collected by filtration and then washed with
cold ethanol. m.p. 137 C, 1.325 g (88%) yields.
Found: C, 72.32; H, 4.32; N, 4.9, C17H12NOCl;
C, 72.47; H, 4.29; N, 4.97 (all values are
Reagents and techniques
2-Hydroxy-1-naphthaldehyde, 2-chloroani-
line, methanol, and CDCl3 were purchased from
Merck (Germany). Ethanol and acetonitrile were
purchased from Aldrich Chemicals. The melting
point was measured on a Gallonkamp appara-
tus using a capillary tube. The elemental analy-
ses were performed on a LECO CHNS-932 C-,
H-, N-analyzer. Infrared absorption spectra were
obtained from a Mattson 1000 FTIR spectrom-
1
given as percentages). IR (KBr, cm ): (Ar H)
3072m, (C N)1621s, (C C)1600s, (C O)
1422 s, 1381 s. 1H NMR (CDCl3);
ppm,
1
eter in KBr discs and reported in cm . Proton
15.22 (s, 1H, OH); 9.18 (d, 1H, CH N, 3 JNHCH
=
(400 MHz) NMR spectra were recorded with a
Bruker DPX FT-NMR spectrometer (CDCl3 as in-
ternal standard).
7.32 Hz); 8.22–6.90 (m, 12H, Ar H). After re-
crystallization, yellow crystals were harvested and
dried in vacuo. [Cu(CH3COO)2] H2O (0.199 g,
0.001 mol) in methanol (50 mL) and N-(2-chloro)-
naphthaldiminato (0.564 g, 0.002 mol) in acetoni-
trile (75 mL) were mixed and heated at 333 K
for 1 h. The solution was filtered and the fil-
trate kept in a beaker at 277 K for crystallization.
Blackcrystalsstartedappearingafter3–4daysand
were then collected by filtration, 0.689 g (90%)
yields (Fig. 1). Found: C, 76.88; H, 4.90; N, 11.23,
The X-ray data collection was performed
on a Rigaku AFC7-S diffractometer employing
graphite-monochromatizedMoK radiation( =
10
˚
0.71073 A). The details of the X-ray data collec-
tion, structure solution, and structure refinement
were given in Table 1 and the fractional atomic co-
ordinates of all nonhydrogen atoms were refined
with anisotropic atomic displacement parame-
ters. Data reduction and corrections for absorption
and crystal decomposition (1.2%) were carried
out using the TEXAN Single Crystal Structure
Analysis Software.11 The structure was solved by
SHELXS-9712 and refined with SHELXL-97.13
The positions of H atoms bonded to C atoms were
˚
calculated (C H distance 0.93 A), and included
in the structure factor calculation using a riding
model. The final fractional atomic coordinates and
thermal parameters were given in Table 2. Bond
distances and angles are listed in Table 3 and an
ORTEP view of the molecular structure is given
in Fig. 2.14
Results and discussion
Recently, the crystal structures of bis
Fig. 1. Reaction scheme.
[N-(2-bromo-4-methylphenyl)-naphthaldiminato]
Uenver
