Ternary inclusion system of chair conformation of 4,6,10,12,16,18,22,24-octahydroxy-2,8,14,20-tetraphenyl-resorcin[4]arene: Selective green synthesis, supramolecular behavior, and biological activity

Article abstract of DOI:10.1080/15421406.2014.905011

Calix[4]resorcinarenes form different types of structural conformations. When their methylene carbons are substituted by four phenyl groups, the molecule can adopt both chair and cone conformations depending on the reaction temperature. The solvent-free s

Full text of DOI:10.1080/15421406.2014.905011

This article was downloaded by: [UQ Library]
On: 15 June 2015, At: 09:28
Publisher: Taylor & Francis
Informa Ltd Registered in England and Wales Registered Number: 1072954 Registered
office: Mortimer House, 37-41 Mortimer Street, London W1T 3JH, UK
Molecular Crystals and Liquid Crystals
Publication details, including instructions for authors and
subscription information:
http://www.tandfonline.com/loi/gmcl20
Ternary Inclusion System of Chair
Conformation of 4,6,10,12,16,18,22,24-
Octahydroxy-2,8,14,20-tetraphenyl-
resorcin[4]arene: Selective Green
Synthesis, Supramolecular Behavior, and
Biological Activity
Solhe F. Alshahateeta, Salah A. Al-Trawneha, Wael A. Al-Zereinib &
Ahmad S. Eldouhaibic
a Department of Chemistry, Mutah University, P.O. Box 7, Mutah,
Alkarak, Jordan
Click for updates
b Department of Biological Sciences, Mutah University, P.O. Box 7,
Mutah, Alkarak, Jordan
c Department of Chemistry, Lebanese University 3rd Branch, Tripoli,
Lebanon
Published online: 15 Dec 2014.
To cite this article: Solhe F. Alshahateet, Salah A. Al-Trawneh, Wael A. Al-Zereini & Ahmad S.
Eldouhaibi (2014) Ternary Inclusion System of Chair Conformation of 4,6,10,12,16,18,22,24-
Octahydroxy-2,8,14,20-tetraphenyl-resorcin[4]arene: Selective Green Synthesis, Supramolecular
Behavior, and Biological Activity, Molecular Crystals and Liquid Crystals, 605:1, 206-215, DOI:
10.1080/15421406.2014.905011
To link to this article: http://dx.doi.org/10.1080/15421406.2014.905011
PLEASE SCROLL DOWN FOR ARTICLE
Taylor & Francis makes every effort to ensure the accuracy of all the information (the
“Content”) contained in the publications on our platform. However, Taylor & Francis,
our agents, and our licensors make no representations or warranties whatsoever as to
the accuracy, completeness, or suitability for any purpose of the Content. Any opinions
and views expressed in this publication are the opinions and views of the authors,
and are not the views of or endorsed by Taylor & Francis. The accuracy of the Content
should not be relied upon and should be independently verified with primary sources
of information. Taylor and Francis shall not be liable for any losses, actions, claims,
proceedings, demands, costs, expenses, damages, and other liabilities whatsoever or

howsoever caused arising directly or indirectly in connection with, in relation to or arising
out of the use of the Content.
This article may be used for research, teaching, and private study purposes. Any
substantial or systematic reproduction, redistribution, reselling, loan, sub-licensing,
systematic supply, or distribution in any form to anyone is expressly forbidden. Terms &
Conditions of access and use can be found at http://www.tandfonline.com/page/terms-
and-conditions

Mol. Cryst. Liq. Cryst., Vol. 605: pp. 206–215, 2014
Copyright © Taylor & Francis Group, LLC
ISSN: 1542-1406 print/1563-5287 online
DOI: 10.1080/15421406.2014.905011
Ternary Inclusion System of Chair Conformation
of 4,6,10,12,16,18,22,24-Octahydroxy-2,8,14,20-
tetraphenyl-resorcin[4]arene: Selective Green
Synthesis, Supramolecular Behavior,
and Biological Activity
SOLHE F. ALSHAHATEET,1,∗ SALAH A. AL-TRAWNEH,1
WAEL A. AL-ZEREINI,2 AND AHMAD S. ELDOUHAIBI3
1Department of Chemistry, Mutah University, P.O. Box 7, Mutah, Alkarak,
Jordan
2Department of Biological Sciences, Mutah University, P.O. Box 7, Mutah,
Alkarak, Jordan
3Department of Chemistry, Lebanese University 3rd Branch, Tripoli, Lebanon
Calix[4]resorcinarenes form different types of structural conformations. When
their methylene carbons are substituted by four phenyl groups, the molecule can
adopt both chair and cone conformations depending on the reaction temperature.
The solvent-free synthesis of 4,6,10,12,16,18,22,24-octahydroxy-2,8,14,20-tetraphenyl-
resorcin[4]arene led to the formation of chair conformer (C2h) rather than the cone
conformer forming a ternary inclusion complex upon crystallization from wet DMSO.
The solid state structure of the ternary inclusion system was determined by single-
crystal X-ray diffraction and proved that the host has adopted the chair conformation.
The supramolecular interactions in the crystal structure of the solvated compound were
carefully investigated. Studies on antimicrobial activities showed that the compound
inhibited the growth of Gram-positive bacteria.
Keywords 4,6,10,12,16,18,22,24-octahydroxy-2,8,14,20-tetraphenyl-resorcin[4]
arene; biological activity; chair-conformation; cone-conformation; DMSO-H2O solvate;
green synthesis; solid-state structure; supramolecular interactions
Introduction
Understanding the self-assembly and the supramolecular interactions of single- and multi-
components crystalline solids is of great interest to chemists due to their interesting applica-
tions and uses. Generally, a careful examination of molecular arrangement and intermolec-
ular interactions in the crystal structure of a given solid compound is helpful to rationalize
the physicochemical properties [1–10].
∗Address correspondence to Dr. Solhe F. Alshahateet, Department of Chemistry, Mutah Univer-
sity, P.O. Box 7, Mutah 61710, Alkarak, Jordan. Tel.: +962–3–2372380. Fax.: +962–3–2375540;
E-mail: solhe alshahateet@yahoo.com
Color versions of one or more of the figures in the article can be found online at
www.tandfonline.com/gmcl.
206

Ternary Inclusion System of Chair Conformation
207
Calixarenes have extensive applications in the biological and pharmaceutical area [11].
Due to their excellent organizing behavior, these classes of synthetic macrocycles have many
functionalities [12] and have often been employed as carriers and spatial organizers of var-
ious kinds of active substituents [13]. They present well-defined conformational properties
and cavities with molecular dimensions that enable them to encapsulate guest drugs [14].
Though most of the calixarene components have been reported for their efficacy against few
microorganism species [15–17], some calixarenes have shown interesting activities against
cancerous cells [14, 18].
Our research group has been interested in designing and preparing different types
of host molecules, and investigating their ability to form host–guest complexes with dif-
ferent guests’ functionalities [19–32]. Herein, we describe the selective synthesis, struc-
tural conformation, supramolecularity, and bioactivity of the chair conformation of 4,6,10,
12,16,18,22,24-octahydroxy-2,8,14,20-tetraphenyl-resorcin[4]arene host 3 (Scheme 1) and
its DMSO-H2O ternary inclusion system, as part of an ongoing project aiming to design,
synthesize, and investigate new calix [4] arenes compounds [33, 34]. The current biologi-
cal study is performed as a baseline for investigation, in our group, for planned calixarene
derivatives synthesis and a structure–activity relationship deduction.
Scheme 1. Synthetic route for 4,6,10,12,16,18,22,24-octahydroxy-2,8,14,20-tetraphenyl-calix[4]
arene host 3.
Experimental Details
Single-crystal X-ray Data Collection and Structure Determination
X-ray quality crystals of compound 3 were obtained by dissolving 30 mg of 3 in 1 mL of
dimethylsulfoxide. Slow evaporation of the resulted solution led to X-ray quality crystals
which were examined under microscope to select a crystal for single-crystal X-ray crystal-
lography. Single-crystal X-ray diffraction data were collected on a Bruker SMART APEX
1000 diffractometer equipped with a CCD detector and MoKα sealed tube at 223(2) K.
SMART [35] was used for collecting frame data, indexing reflection, and determination
of lattice parameters. SAINT [35] was used for integration of intensity of reflections and
scaling. SADABS [36] was used for adsorption correction and SHELXTL [37] was used
for space group, structure determination, and least-square refinements on F2. All hydrogen
atoms were placed in calculated positions for the purpose of structure factor calculations.
All nonhydrogen atoms were refined anisotropically [37], and all hydrogen atoms were
included in calculated positions with isotropic thermal motion linked to that of the bonded

208
S. F. Alshahateet et al.
Table 1. Crystal data and structure refinement for (3)·(DMSO)8·(H2O)3 lattice inclusion
compound
Empirical formula
C68 H94 O19 S8
Formula weight
Temperature
1471.91 g/mol
223(2) K
Wavelength
0.71073 Å
Crystal system
Space group
Unit cell dimensions
Monoclinic
P2(1)/c
a = 23.2700(10) Å
b = 16.1224(6) Å
c = 20.9495(8) Å
7687.9(5) Å3
4
α = 90◦
β = 101.9960(10)◦
γ = 90◦
Volume
Z
Density (calculated)
Absorption coefficient
F(000)
1.272 Mg/m3
0.297 mm−1
3128
Crystal size
Theta range for data collection
Index ranges
0.34 × 0.16 × 0.14 mm3
1.55◦–25.00◦
−25 ≤ h ≤ 27, −19 ≤ k ≤ 19,
−23 ≤ l ≤ 24
43810
Reflections collected
Independent reflections
Completeness to theta
= 25.00◦
13542 [R(int) = 0.0658]
100.0%
Absorption correction
Max. and min. transmission
Refinement method
Sadabs (Sheldrick 2001)
0.9596 and 0.9057
Full-matrix least-squares on
F2
Data/restraints/parameters
Goodness-of-fit on F2
13542/25/914
1.030
Final R indices [I > 2 σ(I)]
R indices (all data)
Largest diff. peak and hole
R1 = 0.0825, wR2 = 0.1875
R1 = 0.1355, wR2 = 0.2131
0.878 and −0.607 e3
atom. The numerical details, data processing, and refinement of the X-ray structure of
(3).(DMSO)8.(H2O)3 lattice inclusion compound are listed in Table 1.
Materials and Physical Measurements
All solvents were used as analytical reagent grade and used as purchased. Melting point
was measured on a Stuart scientific melting point apparatus in open capillary tubes. The
infrared spectrum was recorded over the range 4000–500 cm−1, on a Maltson 5000 FTIR
spectrophotometer. The 1H-NMR and 13C-NMR experiments were conducted on a Bruker
500 MHz at the University of Jordan. Chemical shifts were referenced to TMS as the internal
standard and deuterated dimethylsulfoxide (DMSO-d6) as the solvent. X-ray single crystal

Ternary Inclusion System of Chair Conformation
209
structure determination was carried out at Department of Chemistry, National University
of Singapore.
Preparation of the 4,6,10,12,16,18,22,24-octahydroxy-2,8,14,
20-tetraphenyl-resorcin[4]arene 3
Synthesis of the chair conformation of compound 3 was selectively achieved by using
solvent-free procedure that was published by Scott et al. [38]. Benzaldehyde and resorcinol
(1:1) were mixed together in the presence of catalytic amount of p-toluenesulfonic acid (ca.
5%). The mixture was removed into small mortar and ground manually until it produced a
gummy material which solidified after 2 hr. The crude mixture was reground again, washed
with water, filtered, and dried to give compound 3. IR (KBr), cm−1: 3393, 1614, 1508, 1429,
1280, 1207, 1080, 931, 700, 551; 1H-NMR (500 MHz, DMSO), δ (ppm): 5.64 (s, 4H), 6.33
(s, 4H), 6.74–6.76 (m, 8H), 6.92–7.00 (m, 12 H), 8.58 (bs, 8H); 13C-NMR (125 MHz,
DMSO), δ (ppm): 60.71, 101.96, 102.42, 106.15, 120.24, 124.48, 127.10, 128.52–133.24,
145.68, 152.50, 158.40.
In vitro Antimicrobial Activity
The antibacterial activity of compound 3 was determined by measuring the inhibition zones
in agar diffusion test according to the National Committee for Clinical Laboratory Standards
(NCCLS) [39] using three different concentrations (100, 300, and 500 μg /disk) of the test
sample. In addition, the minimum inhibitory concentration (MIC) was calculated by serial
dilution assay using microtiter plates with 1 mg/mL of the test sample and 100 μg/mL of the
positive control (Chloramphenicol) as starting concentrations. It was performed as follows
[40]: test organisms were incubated overnight (16 hr) prior to the assay. Test samples
(100 μL) were diluted serially in 96 well plates and each microbial strain suspension
(100 μL of 2 × 106 cell/mL) was added in each well. All prepared cultures were incubated
for 24–48 hr. The minimum inhibitory concentration is defined as the lowest concentration
of the substance that inhibited the growth (visible turbidity) of the test microorganisms. The
type of inhibition, bacteriostatic or bactericidal, was determined by platting the preparations
in which there were no visible growths on agar plates with incubation for 24 hr. The test
microorganisms used in this study were Bacillus subtilis (ATCC 6633), Staphylococcus
aureus (ATCC 43300), Escherichia coli (ATCC 25922), Enterobacter aerogenes (ATCC
13048), and Micrococcus luteus (ATCC 10240).
Results and Discussion
Calix[4]resorcinarenes have been prepared in different methods and conditions, both in
the solid state (neat) [38, 41] and in solution [42–45]. Mattay et al. [42] studied the
acid-catalyzed condensation reaction of 2-hydroxyresorcinol with aldehydes in aqueous
media under reflux conditions and at room temperature. The product obtained under room
temperature exhibited the chair-conformation, while the product obtained under reflux
conditions exhibited the cone-conformation.
In the present work, the chair conformation of 4,6,10,12,16,18,22,24-octahydroxy-
2,8,14,20-tetraphenyl-resorcin[4]arene host 3 was selectively prepared in high yield and
purity by direct reaction of resorcinol and benzaldehyde in the presence of catalytic amount
of solid p-toluenesulfonic at room temperature under solvent-free conditions [38]. FTIR,
1H-NMR, 13C-NMR, MS of the prepared compound were in full agreement with what have
been previously reported by Cram et al. [43].

210
S. F. Alshahateet et al.
Figure 1. ORTEP plot of chair conformation of compound 3 showing 50% probability ellipsoids.
Crystallization of
3 from dimethylsulfoxide led to inclusion crystals of
(3).(DMSO)8.(H2O)3 in a monoclinic system with P2(1)/c space group. The asymmet-
ric unit contains one molecule of compound 3, eight DMSO molecules and three water
molecules. Five of the eight DMSO molecules showed disorder of the positions of S, this
is quite usual for DMSO. The crystal structure consists of extensive network of hydrogen
bonds. Hydrogen atoms of the compound 3 and the DMSO molecules were put at calculated
positions. The hydrogen atoms of the water molecules were located from different maps
and refined with restrains in bond lengths and thermal parameters. Compound 3 adopted the
chair-conformation with approximate C2h symmetry. Morales-Morales et al. have reported
on the formation of the cone-conformation of 3 with approximate C2v symmetry [46]. Like
its chair-conformation, the cone-conformation of 3 formed a ternary inclusion complex
with the same space group but with different formula; (3) (DMSO)9 · (H2O). The molecu-
lar structure of 3 including thermal displacement ellipses with 50% probability is illustrated
in Fig. 1. Hydrogen bonding was observed between various phenolic OH groups of the host
molecule 3 and the oxygen atoms of the DMSO and water molecules. Intramolecular
hydrogen bonding does not exist since the shortest distance between hydroxyl groups is
3.82 Å (Fig. 2). However, all hydrogen donor–acceptor components (solvent and water) are
involved in very interesting set of intermolecular hydrogen bonding with different motifs as
presented in Table 2. The completely hydrogen-bonded, solvated structure of molecule 3 is
shown in Fig. 3. Packing of compound 3 as ternary inclusion system ((3).(DMSO)8.(H2O))
is presented in Fig. 4.

Ternary Inclusion System of Chair Conformation
211
Figure 2. Shortest distance between hydroxyl groups of one molecule of compound 3.
Table 2. Hydrogen bond lengths (Å) and angles (◦) for (3)·(DMSO)8·(H2O)3
D-H . . . A
d(D-H)
d(H . . . A)
d(D . . . A)
<(DHA)
O(1)-H(1) . . . O(2S)
O(1)-H(1) . . . S(2)
0.83
0.83
0.83
0.83
0.83
0.83
0.83
0.83
0.83
0.83
0.83
0.83
0.899(10)
0.897(10)
0.897(10)
0.901(10)
0.900(10)
0.900(10)
0.895(10)
0.895(10)
0.895(10)
0.897(10)
1.90
2.95
1.85
1.90
2.80
1.74
1.95
2.80
1.85
2.81
1.90
1.85
1.959(14)
1.834(18)
2.86(4)
1.874(14)
1.95(2)
2.98(5)
1.84(2)
2.85(3)
2.99(3)
1.840(15)
2.709(4)
3.630(3)
2.649(5)
2.724(4)
3.548(3)
2.567(11)
2.723(7)
3.561(5)
2.672(4)
3.501(3)
2.715(5)
2.669(5)
2.853(5)
2.720(6)
3.639(5)
2.773(6)
2.828(6)
3.730(5)
2.705(6)
3.690(4)
3.840(19)
2.730(7)
165.4
140.6
161.3
172.7
151.4
172.3
155.0
153.4
171.7
141.6
168.6
169.6
173(6)
169(7)
146(5)
175(8)
165(8)
142(7)
162(6)
156(5)
159(5)
171(6)
O(3)-H(3) . . . O(3W)#1
O(4)-H(4) . . . O(3S)#2
O(4)-H(4) . . . S(3)#2
O(5)-H(5) . . . O(8SA)#1
O(5)-H(5) . . . O(8S)#1
O(5)-H(5) . . . S(8A)#1
O(6)-H(6) . . . O(1S)#1
O(6)-H(6) . . . S(1)#1
O(7)-H(7) . . . O(1W)
O(8)-H(8) . . . O(7S)#1
O(1W)-H(1WA) . . . O(2S)#3
O(1W)-H(1W) . . . O(6S)
O(1W)-H(1W) . . . S(6)
O(2W)-H(2W) . . . O(3S)
O(2W)-H(2WA) . . . O(1S)#3
O(2W)-H(2WA) . . . S(1)#3
O(3W)-H(3W) . . . O(4S)
O(3W)-H(3W) . . . S(4)
O(3W)-H(3W) . . . S(4A)
O(3W)-H(3WA) . . . O(2W)#4
Notes. Symmetry transformations used to generate equivalent atoms:
#1: x, y+1, z; #2: x−1, y, z; #3: −x+1, y+1/2, −z+1/2; #4: x−1, y−1, z.

212
S. F. Alshahateet et al.
Figure 3. Intermolecular hydrogen bonding present between 3, water, and DMSO.
In Vitro Antimicrobial Activity
The antibacterial activity of 4,6,10,12,16,18,22,24-octahydroxy-2,8,14,20-tetraphenyl-
resorcin[4]arene 3 is presented in Table 3. It was active only against two Gram-positive
bacteria, namely S. aureus and M. luteus at concentrations ≥ 300 μg/disk. Gram-negative
Figure 4. Crystal structure packing of (3)·(DMSO)8·(H2O). All hydrogen atoms were omitted for
clarity.

Ternary Inclusion System of Chair Conformation
213
Table 3. Inhibition zone (mm) caused by chair conformation of compound 3 in agar
diffusion test
Inhibition zone (mm)
Organisms
300 μg/disk
500 μg/disk
Staphylococcus aureus
Micrococcus luteus
10
10
11
13
bacteria were resistant to all tested concentrations. The MIC value of compound 3 against
the susceptible bacteria in serial dilution assay was 250 μg/mL and 125 μg/mL for M.
luteus and S. aureus with biostatic effect, respectively. Chloramphenicol was 100–200 fold
more active than the tested compound in microtiter plate. Similar results were obtained
previously in our group [40] as well as by Abosadiya and his co-researcher [17]. It was
found that Gram-positive bacteria were more susceptible than Gram-negative test strains
at concentrations comparable to the used ones in this work or even higher. In these pre-
vious works the tested Calix[4]resorcinarenes bore para- or ortho- and meta-substituted
phenyl groups at their methylene carbons and the MIC values were larger than those in this
study, indicating the effect of substitution and type of substituent on the bioactivity of these
calixarenes.
Conclusions
Green Chemistry attracted many chemists so that practical methods and reaction conditions
for the preparation of compounds with low environment-damage cost have been devel-
oped. In this paper, a solvent-free route was used to successfully and selectively prepare
4,6,10,12,16,18,22,24-octahydroxy-2,8,14,20-tetraphenyl-resorcin[4]arene 3 with a chair
conformation rather than its boat conformation. The crystal structure of the obtained chair
conformation was determined, analyzed and compared to the boat conformation which
was reported previously. Compound 3 showed a moderate antimicrobial activity against
Gram-positive bacteria. It caused formation of inhibition zones 10–13 mm and has MIC
values 125–250 μg/mL.
Acknowledgments
The authors would like to thank Mutah University, the University of Jordan, and the National
University of Singapore for conducting the experiments needed to complete this work.
Supplementary Material
Crystallographic data (cif) for (3)·(DMSO)8·(H2O)3 have been deposited in the Cambridge
Structural Data Centre (CCDC) with reference number (917787). This data can be obtained
free of charge at http://www.ccdc.cam.ac.uk/conts/retrieving.html [or from the Cambridge
Crystallographic Data Centre (CCDC), 12 Union Road, Cambridge CB2 1EZ, UK; Fax:
+44(0)1223–336033; Email: deposit@ccdc.cam.ac.uk].

214
S. F. Alshahateet et al.
References
[1] Karami, B., Khodabakhshi, S., & Arami, A. (2012). Bull. Korean Chem. Soc., 33, 123.
[2] Hasenknop, B., Lehn, J. M., Kneisel, B. O., Baum, G., & Fenske, D. (1996). Angew Chem. Int.
Ed., 35, 1838.
[3] Day, A. I. (2002). Angew. Chem. Int. Ed., 41, 275.
[4] Qureshi, I., & Memon, S. (2012). Appl Water Sci., 2, 177.
[5] Anderson, S., Anderson, H. L., Bashall, A., McPartlin, M., & Sanders, J. K. M. (1995). Angew.
Chem. Int. Ed., 34, 1096.
[6] Freeman, W. A. (1984). Acta Crystallogr. B, 40, 382.
[7] Schmitt, J.-L., Stadler, A.-M., Kyritsakas, N., & Lehn, J. M. (2003). Helv. Chim. Acta, 86, 1598.
[8] Lehn, J. M. (1993). Science, 260, 1762.
[9] Lehn, J. M. (1995). Supramolecular Chemistry, New York: Wiley-VCH (ISBN
978–3527293117).
[10] Gennady, V., Oshovsky David, N. R., & Willem, V. (2007). Angew Chem. Int. Ed., 46, 2366.
[11] Soomro, A. M., Oad, R. K., Memon, Sh., & Qureshi, I. (2012). Pak J. Anal. Environ. Chem.,
13, 36.
[12] Grare, M., et al. (2007). J. Antimicrob. Chemother., 60, 575.
[13] Salem, A., & Regnouf-de-Vains, J.-B. (2001). Tetrahedron Lett., 42, 7033.
[14] Mokhtari, B., & Pourabdollah, K. (2012). J. Incl. Phenom. Macrocycl. Chem., 73, 1.
[15] Casnati, A., et al. (1996). Bioorg. Med. Chem. Lett., 6, 2699.
[16] Lamartine, R., Tsukada, M., Wilson, D., & Shirata, A. (2002). C. R. Chim., 5, 163.
[17] Abosadiya, H. M., et al. (2013). Molecules, 18, 13369.
[18] Mourer, M., Psychogios, N., Laumond, G., Aubertin, A. M., & Regnouf-de-Vains, J. B. (2010).
Bioorg. Med. Chem., 18, 36.
[19] Alshahateet, S. F., Bishop, R., Craig, D. C., & Scudder, M. L. (2011). Cryst. Growth Des., 11,
4474.
[20] Alshahateet, S. F., Rahman, A. N. M. M., Bishop, R., Craig, D. C., & Scudder, M. L. (2002).
Cryst. Eng. Commun., 4, 585.
[21] Alshahateet, S. F., Bishop, R., Craig, D. C., & Scudder, M. L. (2001). Cryst. Eng. Commun., 3,
225.
[22] Alshahateet, S. F., Bishop, R., Craig, D. C., & Scudder, M. L. (2004). Cryst. Growth Des., 4,
837.
[23] Ghalib, R. M., et al. (2012). J. Chem. Crystallogr., 42, 783.
[24] Ghalib, R. M., et al. (2011). J. Molec. Struct., 1005, 152.
[25] Bishop, R., Scudder, M. L., Craig, D. C., Rahman, A. N. M. M., & Alshahateet, S. F. (2005).
Mol. Cryst. Liq. Cryst., 440, 173.
[26] Alshahateet, S. F., Bishop, R., Craig, D. C., & Scudder, M. L. (2001). Cryst. Eng. Commun.,
3(25), 107.
[27] Alshahateet, S. F., Bishop, R., Craig, D. C., & Scudder, M. L. (2010). Cryst. Growth Des., 10,
1842.
[28] Alshahateet, S. F., et al. (2005). Cryst. Eng. Commun., 7, 139.
[29] Alshahateet, S. F., Bishop, R., Craig, D. C., & Scudder, M. L. (2001). Cryst. Eng. Commun., 3,
264.
[30] Alshahateet, S. F., Bishop, R., Craig, D. C., Kooli, F., & Scudder, M. L. (2008). Cryst. Eng.
Commun., 10, 297.
[31] Alshahateet, S. F., Ong, T. T., Bishop, R., Kooli, F., & Messali, M. (2006). Cryst. Growth Des.,
6, 1676.
[32] Alshahateet, S. F., Bishop, R., Craig, D. C., & Scudder, M. L. (2003). Cryst. Eng. Commun., 5,
417.
[33] Alshahateet, S. F. (2010). J. Chem. Crystallogr., 40, 191.
[34] Alshahateet, S. F., Kooli, F., Messali, M., Judeh, Z. M. A., & AlDouhaibi, A. S. (2007). Mol.
Cryst. Liq. Cryst., 474, 89.

Ternary Inclusion System of Chair Conformation
215
[35] SMART and SAINT. (1996). Software Reference Manual, Version 4.0, Madison, WI: Siemens
Energy and Automation, Inc., Analytical Instrumentation.
[36] Sheldrick, M. (1996). SADABS. Software for Empirical Absorption Correction, Germany:
University of Go¨ttingen.
[37] SHELXTL Reference Manuals. (1996). Semens Energy and Automation, Inc.,Version 5.03,
Madison, WI: Analytical Instrumentation.
[38] Roberts, B. A., Cave, G. W. V., Raston, C. L., & Scott, J. L. (2001). Green Chemistry, 3, 280.
[39] National Committee for Clinical Laboratory Standards (NCCLS). (2004). Performance Stan-
dards for Antimicrobial Susceptibility Testing; Fourteenth Informational Supplement NCCLS
documents M100-S14, NCCLS, Wayne, Pennsylvania.
[40] Alshahateet, S. F., Al-Trawneh, S. A., Al-Zereini, W. A., & Al-Sarhan, S. S. (2013). Arabian J.
Chem., submitted.
[41] Karami, B., Khodabakhshi, S., Safikhani, N., & Arami, A. (2012). Bull. Korean Chem. Soc., 33,
123.
[42] Gerkensmeier, T., et al. (1999). Eur. J. Org. Chem., 1999, 2257.
[43] Tunstad, L. M., Tucker, J. A., Dalcanale, E., Wieser, J., Bryant, J. A., Sherman, J. C., Helgeson,
R. C., Knobler, C. B., & Cram, D. J. (1989). J. Org. Chem., 54, 1305.
[44] Funk, M., Guest, D. P., & Cave, G. W. V. (2010). Tetrahedron Letters, 51, 6399.
[45] Karami, B., Hoseini, S. J., Nikoseresht, S., & Khodabakhshi, S. (2012). Chinese Chem. Lett.,
23, 173.
[46] Gomez-Benitze, V., Toscano, R. A., & Morales-Morales, D. (2004). J. Incl. Phenom. Macrocycl.
Chem., 50, 199.