Synthesis of 1-substituted benzimidazole metal complexes and structural characterization of dichlorobis(1-phenyl- 1H-benzimidazole-kN 3)cobalt(II) and dichlorobis (1-phenyl-1H-benzimidazole-kN 3)zinc(II)

Article abstract of DOI:10.1080/00958972.2011.584620

The Co(II), Zn(II), Ni(II), Cu(II), and Fe(II) complexes of 1-phenylbenzimidazole were synthesized and characterized by NMR and elemental analyses. The crystal structures of dichlorobis(1-phenyl-1H-benzimidazole-N ³)cobalt(II) and dichlorobis(1-phenyl-1H-benzimidazole- kN ³)zinc(II) have been determined by single-crystal X-ray diffraction.

Full text of DOI:10.1080/00958972.2011.584620

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Synthesis of 1-substituted
benzimidazole metal complexes
and structural characterization
of dichlorobis(1-phenyl-1 H -
benzimidazole- κN 3)cobalt(II)
and dichlorobis (1-phenyl-1 H -
benzimidazole- κN 3)zinc(II)
a
Nıhat Şırecı , Ülkü Yilmaz b , Hasan Küçükbay a b , Mehmet
Akkurt c , Zelıha Baktir c , Sevım Türktekın c & Orhan Büyükgüngör
d
a Faculty of Education, Adıyaman University, 02040 Adıyaman,
Turkey
b Department of Chemistry, Faculty of Arts and Sciences, ınönü
University, 44280 Malatya, Turkey
c Department of Physics, Faculty of Arts and Sciences, Erciyes
University, 38039 Kayseri, Turkey
d Department of Physics, Faculty of Arts and Sciences, Ondokuz
Mayis University, 55139 Samsun, Turkey
Version of record first published: 23 May 2011.
To cite this article: Nıhat Şırecı , Ülkü Yilmaz , Hasan Küçükbay , Mehmet Akkurt , Zelıha Baktir ,
Sevım Türktekın & Orhan Büyükgüngör (2011): Synthesis of 1-substituted benzimidazole metal
complexes and structural characterization of dichlorobis(1-phenyl-1 H -benzimidazole- κN
3)cobalt(II) and dichlorobis (1-phenyl-1 H -benzimidazole- κN 3)zinc(II), Journal of Coordination
Chemistry, 64:11, 1894-1902
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Journal of Coordination Chemistry
Vol. 64, No. 11, 10 June 2011, 1894–1902
Synthesis of 1-substituted benzimidazole metal complexes
and structural characterization of dichlorobis(1-phenyl-
1H-benzimidazole-jN3)cobalt(II) and dichlorobis
(1-phenyl-1H-benzimidazole-jN3)zinc(II)
_
_
_
¨
¨
¨
¨
¸
NIHAT S
ꢀ
IRECIy, ULKU YILMAZz, HASAN KUCUKBAY*z,
_ _ _
¨
MEHMET AKKURTx, ZELIHA BAKTIRx, SEVIM TURKTEKINx
¨
¨
¨
¨
and ORHAN BUYUKGUNGOR{
yFaculty of Education, Ad|yaman University, 02040 Ad|yaman, Turkey
_
zDepartment of Chemistry, Faculty of Arts and Sciences, Inonu University,
¨
¨
44280 Malatya, Turkey
xDepartment of Physics, Faculty of Arts and Sciences, Erciyes University,
38039 Kayseri, Turkey
{Department of Physics, Faculty of Arts and Sciences, Ondokuz Mayis University,
55139 Samsun, Turkey
(Received 30 December 2010; in final form 5 April 2011)
The Co(II), Zn(II), Ni(II), Cu(II), and Fe(II) complexes of 1-phenylbenzimidazole were
synthesized and characterized by NMR and elemental analyses. The crystal structures of
dichlorobis(1-phenyl-1 H-benzimidazole-ꢀN3)cobalt(II) and dichlorobis(1-phenyl-1 H-benz-
imidazole-ꢀN3)zinc(II) have been determined by single-crystal X-ray diffraction.
Keywords: Benzimidazole metal complexes; Transition metal complexes; Coordination com-
pounds; Crystal structure
1. Introduction
Nitrogen-containing heterocyclic compounds play an important role in biological
systems and in many industrial fields. Benzimidazoles display a wide range of
pharmacological activities, and are used for therapeutic purposes as antifungal,
antibacterial, antihelmintic, hypotensive, vasodilator, spasmolytic, and antiulcer
activities. In addition to their biological importance, benzimidazoles form stable
complexes with various transition metals [1]. The transition metal complexes of
benzimidazoles are used to model important bioinorganic systems due to their
promising therapeutic potential [2–4]; most works carried out on these classes of
compounds are connected with their medicinal properties [5–7]. If the ring substituents
change, the electron distribution and coordination ability are affected [8, 9].
*Corresponding author. Email: hkucukbay@inonu.edu.tr
Journal of Coordination Chemistry
ISSN 0095-8972 print/ISSN 1029-0389 online ꢁ 2011 Taylor & Francis
DOI: 10.1080/00958972.2011.584620

1-substituted benzimidazole metal complexes
1895
There are many reports of benzimidazole transition metal complexes including
mono-, bi-, and tri-dentate benzimidazoles. Some consist of 2-substituted benzimid-
azole and the others consist of benzimidazole-based mixed ligands [10–14]. Recently, we
reported on the structural and chemical properties of some trimethylsilyl-substituted
benzimidazole derivatives [15, 16].
Most of the studies utilize alkyl-substituted benzimidazole; there is no example
containing 1-phenyl-substituted benzimidazole metal complex in the literature. For this
reason, we focused on the synthesis and characterization of 1-aryl-substituted
benzimidazole-based transition metal complexes.
We report herein the preparation and characterization of cobalt(II),
zinc(II), nickel(II), copper(II), and iron(II) coordination compounds with 1-phenyl-
benzimidazole. The crystal structures of dichlorobis(1-phenylbenzimidazole-1
H-benzimidazole-ꢀN3)cobalt(II) (1) and dichlorobis(1-phenylbenzimidazole-1 H-benzi-
midazole-ꢀN3)zinc(II) (2) were determined by single-crystal X-ray diffraction.
2. Experimental
All preparations were carried out in an atmosphere of purified argon using standard
Schlenk techniques. Starting materials and reagents used in reactions were supplied
commercially from Aldrich or Merck Chemical Co. Solvents were dried according to
standard methods and freshly distilled prior to use. 1H-NMR (300 MHz) and 13C-NMR
(75 MHz) spectra were recorded using a Bruker DPX-300 high performance digital FT
NMR spectrometer. Because of the paramagnetic cobalt, nickel, copper, and iron,
1H-NMR spectra of these complexes were recorded as broad peaks through diluted
sample solutions with doubling of scans. Infrared (IR) spectra were recorded using an
ATR unit from 4000 to 200 cmꢀ1 on a Perkin-Elmer FT-IR spectrophotometer.
Elemental analyses were performed with a LECO CHNS-932 elemental analyzer at the
_
Scientific and Technological Research Centre of Inonu University (Malatya-Turkey).
¨
¨
UV-Vis spectra were measured on a Perkin-Elmer Lambda 35 spectrophotometer.
Melting points were recorded using an electrothermal-9200 melting point apparatus and
are uncorrected. Magnetic measurements were carried out on a Sherwood Scientific
apparatus at room temperature by Gouy’s method using CuSO4 ꢁ 5H2O as calibrant
and were corrected for diamagnetism by applying Pascal’s constants.
1-Phenylbenzimidazole was synthesized according to the literature procedure [17, 18].
Compounds 1–5 were synthesized from 1-phenylbenzimidazole with cobalt(II), zinc(II),
nickel(II), copper(II), and iron(II) chloride in DMF (scheme 1).
2.1. Preparation of dichlorobis(1-phenylbenzimidazole-1 H-benzimidazole-
ꢀN3)cobalt(II) (1)
A solution of 1-phenylbenzimidazole (1.75 g, 9.00 mmol) and cobalt(II) chloride (0.58 g,
4.50 mmol) in DMF (4 cm3) was heated under reflux for 2 h. The mixture was then
cooled to room temperature, after which solvent was removed from the filtrate in vacuo.
The precipitate was then crystallized from EtOH/DMF (2 : 1). Yield: 2.06 g (88%); m.p.:

1896
N. Sꢀ |rec| et al.
MX2 = CoCl2
MX2 = ZnCl2
1
2
3
4
5
X
M
X
N
N
N
MX2
DMF
N
N
N
MX2 = NiCl2
MX2 = CuCl2
MX2 = FeCl2
Scheme 1. Synthesis of 1-phenylbenzimidazoles metal complexes.
207–208ꢂC. Anal. Calcd for C26H20N4CoCl2 (%): C, 60.25; H, 3.89; N, 10.81. Found
(%): C, 60.21; H, 3.85; N, 10.80. ꢁ(N¼C): 1481 cmꢀ1
Similarly, 2–5 were obtained by the reaction of 1-phenylbenzimidazole with zinc
chloride, nickel chloride, copper chloride, and iron chloride, respectively.
.
2.2. Dichlorobis(1-phenylbenzimidazole-1 H-benzimidazole-ꢀN3)zinc(II) (2)
Yield: 2.16 g, 91%; m.p.: 223–224ꢂC. Anal. Calcd for C26H20N4ZnCl2 (%): C, 59.51;
H, 3.84; N, 10.68. Found (%): C, 59.45; H, 3.82; N, 10.63. ꢁ(N¼C): 1481 cmꢀ1. 1H NMR
(DMSO-d6): ꢂ 8.74 (s, 2 H, NCHN), 7.97–7.37 (m, 18 H, C6H4 and C6H5). 13C NMR
(DMSO-d6): ꢂ 144.1 (NCHN), 142.6, 135.9, 133.4, 130.6, 128.8, 124.6, 123.6, 119.9,
111.5 (C6H4 and C6H5).
2.3. Dichlorobis(1-phenylbenzimidazole-1 H-benzimidazole-ꢀN3)nickel(II) (3)
Yield: 1.99 g, 85%; m.p.: 102–103ꢂC. Anal. Calcd for C26H20N4NiCl2 (%): C, 60.28;
H, 3.89; N, 10.81. Found (%): C, 60.24; H, 3.88; N, 10.80. ꢁ(N¼C): 1481 cmꢀ1. 1H NMR
(DMSO-d6): ꢂ 8.12 (br s, 2 H, NCHN), 7.77–7.03 (m, 18 H, C6H4 and C6H5).
2.4. Dichlorobis(1-phenylbenzimidazole-1 H-benzimidazole-ꢀN3)copper(II) (4)
Yield: 2.13 g, 90%; m.p.: 209–210ꢂC. Anal. Calcd for C26H20N4CuCl2 (%): C, 59.72;
H, 3.86; N, 10.71. Found (%): C, 59.61; H, 3.81; N, 10.62. ꢁ(N¼C): 1481 cmꢀ1. 1H NMR
(ꢂ, DMSO-d6): ꢂ 8.00 (br s, 2 H, NCHN), 7.70–6.69 (m, 18 H, C6H4 and C6H5).
2.5. Dichlorobis(1-phenylbenzimidazole-1 H-benzimidazole-ꢀN3)iron(II) (5)
Yield: 2.02 g, 87%; m.p.: 217–218ꢂC. Anal. Calcd for C26H20N4FeCl2 (%): C, 60.61;
H, 3.91; N, 10.87. Found (%): C, 60.58; H, 3.86; N, 10.83. ꢁ(N¼C): 1480 cmꢀ1. 1H NMR
(ꢂ, DMSO-d6): ꢂ 8.64 (br s, 2 H, NCHN), 7.20–7.80 (m, 18 H, C6H4 and C6H5).

1-substituted benzimidazole metal complexes
1897
Figure 1. (a) View of 1, with the atom numbering scheme. Displacement ellipsoids for non-H atoms are
drawn at the 30% probability level. (Symmetry code: (a) 1 ꢀ x, y, 1 ꢀ z). (b) View of 2, with the atom
numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 50% probability level.
2.6. Crystal structure determinations of 1 and 2
Crystallographic data for 1 and 2 were collected at 296(2) K on a STOE IPDS 2
˚
diffractometer with Mo-Ka radiation (ꢃ ¼ 0.71073 A); crystal structures were solved by
direct methods using SIR97 structure solution program [19]. Refinement was performed
by the difference-Fourier method of SHELXL97 [20]. All hydrogens were positioned
geometrically and refined using a riding model. ORTEP [21] representations of 1 and 2
are in figure 1(a) and (b). Table 1 lists cell information, data collection parameters, and
refinement data. Selected bond lengths and angles are given in table 2.

1898
N. Sꢀ |rec| et al.
Table 1. Crystallographic data and structure refinements for 1 and 2.
Compound
1
26H20Cl2CoN4
2
C26H20Cl2N4Zn
524.75
296(2)
Triclinic
Empirical formula
Formula weight
Temperature (K)
Crystal system
Space group
C
518.29
296(2)
Monoclinic
C2
Cell parameters from
18,464 reflections
20.0470(12)
6.0254(2)
12.1069(7)
–
126.060(4)
–
1182.21(12), 2
1.456
0.97
ꢀ
P1
ꢂ
˚
Unit cell dimensions (A,
)
Cell parameters from
15,925 reflections
7.3346(5)
10.1589(7)
16.9840(11)
77.161(5)
85.537(5)
78.869(5)
1209.85(14), 2
1.441
a
b
c
ꢄ
ꢅ
ꢆ
3
˚
Volume (A ), Z
Calculated density, Dx (Mg mꢀ3
)
Absorption coefficient (mmꢀ1
Crystal size (mm3)
F(000)
)
1.26
0.24 ꢃ 0.38 ꢃ 0.62
0.52 ꢃ 0.62 ꢃ 0.68
530
536
2.1–27.2
ꢇ range (ꢂ)
2.1–28.0
9045
2459
2431
152
1.067
0.021, 0.056
ꢀ0.16, 0.25
Number of reflections measured
Number of unique reflections
Number of observed reflections I 4 2ꢈ(I)
Number of refined parameters
Goodness of fit on F2
14,247
3666
2862
298
1.174
0.045, 0.153
ꢀ0.34, 0.28
R[F2 4 2ꢈ(F2)], wR2
ꢀ3
˚
Residual density (e A
)
ꢂ
˚
Table 2. Selected bond lengths (A) and angles ( ) for 1 and 2.
1
2
Co(1)–Cl(1)
Co(1)–N(1)
N(1)–C(12)
N(1)–C(13)
N(2)–C(1)
N(2)–C(7)
N(2)–C(13)
C(7)–C(12)
2.2403(6)
2.0313(13)
1.4037(19)
1.307(3)
1.428(3)
1.391(2)
1.352(2)
1.388(3)
Zn(1)–Cl(1)
Zn(1)–Cl(2)
Zn(1)–N(1)
Zn(1)–N(3)
N(1)–C(1)
N(1)–C(13)
N(3)–C(14)
N(3)–C(26)
2.2243(14)
2.2360(14)
2.027(4)
2.022(3)
1.403(6)
1.307(6)
1.399(6)
1.311(6)
Cl(1)–Co(1)–N(1)
Cl(1)–Co(1)–Cl(1)a
Cl(1)–Co(1)–N(1)a
Cl(1)a–Co(1)–N(1)
N(1)–Co(1)–N(1)a
Cl(1)a–Co(1)–N(1)a
Co(1)–N(1)–C(12)
Co1–N1–C13
109.12(4)
116.53(2)
109.34(5)
109.34(5)
102.46(5)
109.12(4)
132.33(12)
122.39(11)
Cl(1)–Zn(1)–Cl(2)
Cl(1)–Zn(1)–N(1)
Cl(1)–Zn(1)–N(3)
Cl(2)–Zn(1)–N(1)
Cl(2)–Zn(1)–N(3)
N(1)–Zn(1)–N(3)
Zn(1)–N(1)–C(1)
Zn(1)–N(1)–C(13)
121.20(6)
102.43(12)
112.36(12)
109.52(12)
102.13(11)
108.97(15)
128.2(3)
125.4(3)
Symmetry code: (a) 1 ꢀ x, y, 1 ꢀ z.
3. Results and discussion
1-Phenylbenzimidazole was synthesized from N-phenyl-1,2-diaminobenzene and formic
acid in 4N HCl according to Phillips’ method [17, 18]. The cobalt(II), zinc(II),
nickel(II), copper(II), and iron(II) coordination compounds of 1-phenylbenzimidazole

1-substituted benzimidazole metal complexes
1899
Table 3. Electronic absorption spectral bands and magnetic moments of 1-phenylbenzimidazole and their
complexes 1–5.
Electronic absorption bandsa, ꢃmax (nm)
Intraligand and charge
transfer bands
Magnetic moment,
ꢊeff (B.M.)
Compound
d–d Bands
1-Phenylbenzimidazole
295, 245
470, 294, 212
292, 232, 223
273, 252, 237
286, 244, 233
280, 224, 215
–
675
–
453
439
–
–
4.13
Diamagnetic
2.88
1.71
1
2
3
4
5
2.40
aDMSO used as a solvent.
were obtained through reflux in DMF. The complexes were crystallized from an
EtOH/DMF mixture. The IR spectra of 1–5 are closely related to that of free
1-phenylbenzimidazole.
IR spectra of complexes show that the strong ꢁ(C¼N) in free 1-phenylbenzimidazoles
at 1500 cmꢀ1 shifts to 1481 cmꢀ1 for Co(II), Zn(II), Ni(II), and Cu(II) complexes and to
1480 cmꢀ1 for Fe(II) complex. The red shift indicates that the tertiary nitrogen is
coordinated. Such coordination of benzimidazoles to metal has been reported in the
literature [4, 6, 8, 22–25]. In the far-IR spectrum a few new bands with respect to the
1-phenylbenzimidazole are observed. Bands at 330 and 251 cmꢀ1 for 1 correspond to
ꢁ(Co–Cl) and ꢁ(Co–Nbenzimidazole), respectively. These bands are also observed at
311 cmꢀ1, ꢁ(Zn–Cl) and 265 cmꢀ1, ꢁ(Zn–Nbenzimidazole) for 2, 347 cmꢀ1, ꢁ(Ni–Cl) and
226 cmꢀ1, ꢁ(Ni–Nbenzimidazole) for 3, 345 cmꢀ1, ꢁ(Cu–Cl) and 243 cmꢀ1, ꢁ(Cu–
N
benzimidazole) for 4, and 344 cmꢀ1, ꢁ(Fe–Cl) and 241 cmꢀ1, ꢁ(Fe–Nbenzimidazole) for 5.
1
As expected, coordination to Zn(II) and Fe(II) shifts the H NMR signals of the
complexes downfield from those of the free ligand (Dꢂ ¼ 0.59 and 0.49 ppm, respec-
tively) for the proton on 2-position of imidazole ring. The aromatic protons in Zn(II)
complex were not shifted significantly downfield (Dꢂ ꢄ 0.07 ppm). But in Co(II), Ni(II),
and Cu(II) complexes, unexpected upfield shifts were observed for the proton on the
2-position of imidazole ring and aromatic protons about 0.03–0.35 and 0.12–0.33 ppm.
Aromatic protons of Fe(II) also showed upfield shifts of 0.10 ppm. These results
arise from paramagnetic properties of Co(II), Ni(II), Cu(II), and Fe(II) atoms; the
proton NMR of Co(II), Ni(II), Cu(II), and Fe(II) were recorded as broad peaks in
diluted solvents with more scans. Even with these conditions, we could not
observe carbon signals for these paramagnetic complexes. Similar broad 1H-NMR
peaks were also reported for paramagnetic complexes in the literature [16, 22]. The
carbon peak on 2-position of imidazole ring of the ligand was shifted downfield about
1.83 ppm after coordination to Zn(II), which is very low compared to similar complexes
containing alkyl-substituted benzimidazole complexes [16]. This unexpected shift
probably arises from ꢉ-electron pushing of the phenyl group to the imidazole ring
through space.
UV-Vis spectra of 1-phenylbenzimidazole and its complexes (1, 2, 3, 4, and 5) were
determined from 190 to 800 nm in DMSO (table 3). 1-Phenylbenzimidazole has
absorption maxima at 245 and 295 nm, attributed to ꢉ–ꢉ* and n–ꢉ* transitions,
respectively. In the complexes, these peaks shift to shorter wavelengths by 1–22 and

1900
N. Sꢀ |rec| et al.
8–33 nm, respectively. The d–d bands for the cobalt(II), nickel(II), and copper(II)
ꢀ1 ꢀ1 cmꢀ1), 453 nm
ꢀ1 ꢀ1 cmꢀ1), respectively. The
complexes 1, 3, and 4 were observed as 675 nm (" ¼ 489 (mol L
)
(" ¼ 724 (mol L
)
benzimidazole complexes studied here show tetrahedral geometry.
ꢀ1 ꢀ1 cmꢀ1), and 439 nm (" ¼ 771 (mol L
)
Co(II), Ni(II), Cu(II), and Fe(II) complexes (1, 3, 4, and 5) are paramagnetic with
magnetic susceptibilities of 4.13, 2.88, 1.77, and 2.40 B.M., respectively.
3.1. Description of the crystal structure
A half of 1 connects on its other half by a two-fold rotation axis (symmetry code: (a)
1 ꢀ x, y, 1 ꢀ z) which passes through the cobalt and along the b-direction. The CoII is
four-coordinate with two chlorides and two benzimidazoles. The coordination
geometry is distorted tetrahedral with the Cl–Co–Cl angle, 116.53(2)ꢂ, being signifi-
cantly larger than the Cl–Co–N angles (average 109.23 (5)ꢂ) and the N–Co–N angle
(102.46 (5)ꢂ).
In 1, the average values of Co–N and Co–Cl bond lengths (2.0313(13) and
˚
2.2403(6) A) are nearly equal to the corresponding lengths in similar compounds [15, 26,
27]. The benzimidazole ring system (N(1)/N(2)/C(7)–C(13)) is almost planar, with
˚
˚
˚
maximum deviations of ꢀ0.017(2) A for C(7), ꢀ0.015(2) A for C(12), and 0.010(2) A for
C(10). The dihedral angle between the benzimidazole and phenyl rings (C(1)–C(6)) is
47.77(8)ꢂ [28]
In the crystal structure of 1, molecular packing is stabilized by van der Waals
interactions. Molecular conformation of 1 is stabilized by intramolecular C(11)–
ꢂ
˚
H(11) ꢁ ꢁ ꢁ Cl(1) interaction (C(11) ꢁ ꢁ ꢁ Cl(1) ¼ 3.5482(19) A, C(11)–H(11) ꢁ ꢁ ꢁ Cl(1) ¼ 142 ).
The molecular packing of 1 is shown in figure 2(a).
The central zinc in 2 is four-coordinate with two chlorides and two benzimidazoles in
distorted tetrahedral geometry, Cl(1)–Zn(1)–Cl(2) ¼ 121.20(6)ꢂ ((Cl–Zn–N)average
¼
106.61(12)ꢂ and N(1)–Zn(1)–N(3) ¼ 108.97(15)ꢂ). The Zn–N and Zn–Cl bond lengths
˚
(2.0313(13) and 2.2403(6) A) are similar to those in similar compounds [21–23, 28].
The two benzimidazole rings in 1 are almost planar, with puckering parameters
Q(2) ¼ 0.026(5) A, ꢋ(2) ¼ 269(11)ꢂ for N(1)/N(2)/C(1)–C(6)/C(13) and Q(2) ¼
˚
ꢂ
˚
0.009(5) A, ꢋ(2) ¼ 249(33) for N(3)/N(4)/C(14)–C(19)/C(26). The dihedral angle
between them is 64.82(17)ꢂ. The phenyl rings with benzimidazole rings attached to
them make dihedral angles of 54.5(2)ꢂ for (C(7)–C(12))phenyl and 49.1(2)ꢂ for (C(20)–
C(25))phenyl, while the phenyl rings form a dihedral angle of 51.8(3)ꢂ with each other.
In the crystal structure of 2, molecular packing is stabilized by weak ꢉ–ꢉ stacking
i
i
˚
˚
interactions [Cg2 ꢁ ꢁ ꢁ Cg5 ¼ 3.947(3) A and Cg5 ꢁ ꢁ ꢁ Cg5 ¼ 3.728(3) A; symmetry code: (i)
1 ꢀ x, 1 ꢀ y, 2 ꢀ z, where Cg2 and Cg5 are centroids of the N(3)/N(4)/C(14)/C(19)/C(26)
1 H-imidazole ring and the C(14)–C(19) benzene ring, respectively] and van der Waals
interactions. The molecular packing of 2 is shown in figure 2(b).
4. Conclusion
We have synthesized Co(II), Zn(II), Ni(II), Cu(II), and Fe(II) complexes of 1-phenyl
benzimidazole, the first example of 1-phenyl-substituted benzimidazole

1-substituted benzimidazole metal complexes
1901
Figure 2. (a) The packing of 1 in the unit cell viewed down the b-axis. All hydrogens have been omitted for
clarity. (b) The packing of 2 in the unit cell viewed down the b-axis. All hydrogens have been omitted for
clarity.
metal complexes. X-ray diffraction analysis of dichlorobis(1-phenylbenzimidazole-
1 H-benzimidazole-ꢀN3)cobalt(II) and dichlorobis(1-phenylbenzimidazole-1 H-benzimi-
dazole-ꢀN3)zinc(II) show that cobalt and zinc are coordinated tetrahedrally by two
chlorides and two nitrogens from two benzimidazole rings.
Supplementary material
Crystallographic data for the structures in this article have been deposited with the
Cambridge Crystallographic Data Centre with supplementary publication CCDC

1902
N. Sꢀ |rec| et al.
Nos. 805619 (1) and 805620 (2). These data can be obtained free of charge via http://
www.ccdc.cam.ac.uk/conts/retrieving.html, or from the Cambridge Crystallographic
Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; Fax: (þ44) 1223-336-033; or
E-mail: deposit@ccdc.cam.ac.uk.
Acknowledgments
This work was financially supported the Ad|yaman University Research Fund
¨
(ADYUBAP-EFBAP 2010-0005).
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