6
26
Zhao et al.
2C
¡
2
Table 5. Antibacterial activities of AMB¢2HCl, AEB¢2HCl and [H APB ][Cl ] ¢2H O.
2
2
Inhibition zone diameter (mm)
¡
1
Compounds
Dose (ug·mL
)
S. aureus
E. coli
AMB¢2HCl
125
¡
16
19
18
21
25
¡
¡
¡
¡
¡
¡
¡
¡
¡
¡
¡
2
5
50
00
AEB¢2HCl
125
2
5
50
00
2
C
¡
2
[
H APB ][Cl ] ¢2H O
125
2
2
2
5
50
00
¡
11
¡
DMSO
A.R.
that the only increase in lipophilicity does not result in
enhancing antimicrobial activity for the homologous family.
Some highly lipophilic compounds may have low antibacte-
rial activity because the time needed for the diffusion into the
bacterial cell might be too long compared to their biological
half-life. So, we believe that the difference in antibacterial
activity of the three compounds maybe due to differences in
lipophilicity of the compounds.
3. Millward, A. R.; Yaghi, O. M. Metal–organic frameworks with
exceptionally high capacity for storage of carbon dioxide at room
temperature. J. Am. Chem. Soc. 2005, 127, 17998–17999.
4
. Rowsell, J. L. C.; Yaghi, O. M. Effects of functionalization, cate-
nation, and variation of the metal oxide and organic linking units
on the low-pressure hydrogen adsorption properties of metal-
[
34]
¡
organic frameworks. J. Am. Chem. Soc. 2006, 128, 1304–1315.
5. Agnihotri, P.; Eringathodi, E.; Paul, P.; Ghosh, P. K. Synthesis,
crystal structures, cation-binding properties and the influence of
intramolecular C–H¢¢¢O Interactions on the complexation behav-
iour of a family of cone p-tert-Butylcalix[4]arene-crown-5 com-
pounds. Eur. J. Inorg. Chem. 2006, 17, 3369–3381.
Conclusions
6
. Kumar; D. K.; Das, A.; Dastidar, P. Metalloporphyrin-based inclu-
sion materials: exploiting ligating topologies and hydrogen-bond-
ing backbones in generating new supramolecular architectures.
Inorg. Chem. 2007, 46, 7351–7361.
We have synthesized and structurally characterized the title
2
C
¡
compound [H APB ][Cl ] ¢2H O. X-ray crystallography
2
2
2
reveals that the benzimidazole and amine nitrogen atoms are
protonated. The [H APB ] ions are linked into a 3D frame-
7. Stahly, G. P. Diversity in single- and multiple-component crystals.
The search for and prevalence of polymorphs and cocrystals. Cryst.
Growth Des. 2007, 7, 1007–1026.
2
C
2
work by chloride ions and two water molecules via
N ꢀꢀ H¢¢¢O, N ꢀꢀ H¢¢¢Cl, O ꢀꢀ H¢¢¢O and O ꢀꢀ H¢¢¢Cl hydrogen
bonds, C ꢀꢀ H¢¢¢p and p-p packing interactions between adja-
8
. Vogt, F. G.; Clawson, J. S.; Strohmeier, M.; Edwards, A. J.; Pham,
T. N.; Watson, S. A. Solid-state NMR analysis of organic cocrys-
tals and complexes. Cryst. Growth Des. 2009, 9, 921–937.
2
C
¡
2
cent benzimidazole rings. [H APB ][Cl ] ¢2H O exhibited
9. Wang, W.-H.; Xi, P.-H.; Su, X.-Y.; Lan, J.-B.; Mao, Z.-H.; You, J.-
S.; Xie, R.-G. Supramolecular assemblies of multifunctional diimi-
dazole and dicarboxylic acids via various hydrogen bonds and X¢¢¢p
2
2
lower antibacterial activity against S. aureus than the familiar
compounds, AMB¢2HCl and AEB¢2HCl.
(
X D p, CH) interactions. Cryst. Growth Des. 2007, 7, 741–746.
1
0. Zaworotko, M. J. Design and construction of coordination poly-
mers. J. Am. Chem. Soc. 2010, 132, 7821–7821.
Supplementary Materials
1
1. Zhang, J. J.; Wojtas, L.; Larsen, R. W.; Eddaoudi, M.; Zaworotko,
M. J. Temperature and concentration control over interpenetration
in a metal¡organic material. J. Am. Chem. Soc. 2009, 131, 17040.
CCDC 930400 contains the supplementary crystallographic
vates with interacting Ni atoms. Cryst. Growth Des. 2009, 9, 1194–
1
200.
1
3. Branzea, D. G.; Guerri, A.; Fabelo, O.; Ruiz-Perez, C.; Chamor-
eau, L.-M.; Sangregorio, C.; Caneschi, A.; Andruh, M. Heterobinu-
clear complexes as tectons in designing coordination polymers.
Cryst. Growth Des. 2008, 8, 941–949.
1
1
1
1
4. Gogoi, A.; Das, G. Charge-assisted complexation of anions of dif-
ferent dimensionality by benzimidazole-based receptors bearing
References
-OH functionality. Cryst. Growth Des. 2012, 12, 4012–4021.
5. Sundberg, R. J.; Yilmaz, I.; Mente, D. C. Coordination chemistry
of imidazole derivatives. A search for carbon-bound chelates with
first-row transition metal ions. Inorg. Chem. 1977, 16, 1470–1476.
6. Santoro, S. W.; Joyce, G. F.; Sakthivel, K.; Gramatikova, S.; Bar-
bas, C. F. RNA cleavage by a DNA enzyme with extended chemi-
cal functionality. J. Am. Chem. Soc. 2000, 122, 2433–2439.
1
. Nouar, F.; Eubank, J. F.; Bousquet, T.; Wojtas, L.; Zaworotko, M.
J.; Eddaoudi, M. Supermolecular building blocks (SBBs) for the
design and synthesis of highly porous metal-organic frameworks. J.
Am. Chem. Soc. 2008, 130, 1833–1835.
2
. Uemura, K.; Saito, K.; Kitagawa, S.; Kita, H. Hydrogen-bonded
porous coordination polymers: structural transformation, sorption
properties, and particle size from kinetic studies. J. Am. Chem. Soc.
7. Arrowsmith, J.; Jennings, S. A.; Clark, A. S.; Stevens, M. F. G.
1
Antitumor imidazotetrazines. 41. Conjugation of the antitumor
2
006, 128, 16122–16130.