A facile approach for the synthesis of indenoimidazole derivatives and their supramolecular study

Article abstract of DOI:10.1007/s12039-016-1181-2

The structures of the title Indeno-imidazole compounds, have been determined by FTIR, NMR, mass and single crystal X-ray diffraction. 3a,8a-Dihydroxy-1-phenyl-1,3,3a,8a-tetrahydro-indeno[1,2-d]imidazole-2,8-dione (1) crystallizes in the monoclinic, space group P2₁/c with a = 12.0913(7) ?, b = 5.7204(3) ?, c = 19.8168(11) ?, α= 90.00 ^°, β= 103.6650(10) ^°, γ= 90.00 ^°, V = 1331.87(13) ? ³, Z = 4; while 3a,8a-Dihydroxy-1-phenyl-2-thioxo-2,3,3a,8a-tetrahydro-1H-indeno[1,2-d]imidazol-8-one (2) crystallizes in the monoclinic, space group P2₁/c with a = 11.0101(5) ?, b = 6.8421(3) ?, c = 21.1243(9) ?, α= 90.00 ^°, β= 110.771(2) ^°, γ= 90.00 ^°, V = 1487.91(11) ? ³, Z = 4. Solid-state crystal structures of compounds 1 and 2 are presented here in terms of crystal engineering and supramolecular chemistry. Replacement of oxygen atom of compound 1 by sulfur atom in compound 2 forced compound 2 to hold water molecules and formed the hydrated form. [Figure not available: see fulltext.]

Full text of DOI:10.1007/s12039-016-1181-2

c
J. Chem. Sci. ꢀ Indian Academy of Sciences.
DOI 10.1007/s12039-016-1181-2
A facile approach for the synthesis of indenoimidazole derivatives and
their supramolecular study
RAZA MURAD GHALIBa,c,∗, SAYED HASAN MEHDIb, ROKIAH HASHIMc,
SOLHE F ALSHAHATEETd and OTHMAN SULAIMANc
aDepartment of Chemistry, Faculty of Sciences and Arts–Khulais, University of Jeddah, P.O. Box-355,
Postal Code-21921, Jeddah, Kingdom of Saudi Arabia
bDepartment of Chemistry, S P G College, University of Lucknow, Lucknow, Uttar Pradesh 226 020, India
cSchool of Industrial Technology, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
dDepartment of Chemistry, Mutah University, P.O. BOX 7, Mutah 61710, Karak, Jordan
e-mail: raza2005communications@gmail.com
MS received 15 September 2015; revised 17 July 2016; accepted 17 September 2016
Abstract. The structures of the title Indeno-imidazole compounds, have been determined by FTIR,
NMR, mass and single crystal X-ray diffraction. 3a,8a-Dihydroxy-1-phenyl-1,3,3a,8a-tetrahydro-indeno[1,2-
d]imidazole-2,8-dione (1) crystallizes in the monoclinic, space group P21/c with a = 12.0913(7) Å, b =
5.7204(3) Å, c = 19.8168(11) Å, α = 90.00◦, β = 103.6650(10)◦, γ = 90.00◦, V = 1331.87(13) Å3, Z = 4;
while 3a,8a-Dihydroxy-1-phenyl-2-thioxo-2,3,3a,8a-tetrahydro-1H-indeno[1,2-d]imidazol-8-one (2) crys-
tallizes in the monoclinic, space group P21/c with a = 11.0101(5) Å, b = 6.8421(3) Å, c = 21.1243(9) Å,
α = 90.00◦, β = 110.771(2)◦, γ = 90.00◦, V = 1487.91(11) Å3, Z = 4. Solid-state crystal structures of com-
pounds 1 and 2 are presented here in terms of crystal engineering and supramolecular chemistry. Replacement
of oxygen atom of compound 1 by sulfur atom in compound 2 forced compound 2 to hold water molecules and
formed the hydrated form.
Keywords. Supramolecular assemblies; hydrated structure; intermolecular non-covalent interactions.
1. Introduction
emphasizing their potential role as a source for ratio-
nal design of potent anti-proliferative agents.4 Devi in
2012 synthesized ninhydrin guanidinium chloride as
3a,8b-dihydroxy-4-oxo-1H,2H,3H,3aH,4H,8bH-indeno
[1,2-d]imidazolidin-2-iminium chloride. The structure
was confirmed by single crystal X-ray and spectral
analysis.5 Shapiro reported cyclization reactions of
ninhydrin with aromatic amines and ureas to give
indanoimidazole derivatives.6 Hossaini in 2013 intro-
duced a facile, green and efficient method for synthesis
of new class of imidazole derivatives via one-pot
condensation of primary amines with trichloroacetoni-
trile and ninhydrin in water.7 In an important study,
Chatterjie reported the synthesis of imidazole deriva-
tives with strong anticonvulsive activity against seizures
induced by pentylenetetrazole and low toxicity, by
the cyclocondensation of ninhydrin with 1-propyl-
1-alkyl-, 1-butyl-, 1-phenylurea, 6-aminouracil, and
1,3-dimethyl-6-aminouracil.8 Our previous studies,
reported synthesis, crystal structures, supramolecular-
ity of several indenoimidazoles with antimicrobial and
cholinesterase enzymes inhibitory activities.9,20,22 The
title adducts have been synthesized in minimum time
(15 min) with maximum yields (95%).
Ninhydrin (1,2,3-indanetrione monohydrate) has a
versatile role in organic synthesis. C-2 position of ninhydrin
is more reactive towards nucleophiles and undergoes
acid catalyzed cyclization reactions with various urea
derivatives to give indano-imidazoles. Indano-imida-
zoles are heterocyclic organic compounds of wide
biological importance.1,2 Chen et al., synthesized a
series of novel hybrid Indeno[5,6-b]furan-imidazole
compounds by the reactions of tricyclic indeno[5,6-
b]furan and imidazole and evaluated toxicity in vitro
against a panel of human tumor cell lines. Their
results suggest that the existence of benzimidazole ring
and substitution of the imidazolyl-3-position with a
naphthylacyl group were vital for modulating cytotoxic
activity.3 Sarkarzadeh et al., synthesized imidazole-
based indeno[1,2-b]quinoline-9,11-dione derivatives and
evaluated antiproliferative activity by using MTT assay.
Their results suggested that some of the imidazole-
substituted indeno[1,2-b]quinoline-9,11-dione com-
pounds may act as efficient anticancer agents in vitro,
∗For correspondence

Raza Murad Ghalib et al.
Nowadays, supramolecular chemists are interested in
design, synthesis, and characterization of supramole-
cular assemblies, which have the ability to work as
functional materials. Understanding the intermolecular
non-covalent interactions that are present in the crys-
tal structure of a given solid compound will lead to a
greater understanding of its useful properties.10 18 This
understanding is important and crucial to understand,
hopefully, biological processes.19 34 In this paper, com-
pounds 1 and 2 were prepared by the cyclocondensation
of ninhydrin with 1-phenylurea and 1-phenyl thiourea.
Furthermore, their solid-state structures and the
supramolecular behavior were determined, analyzed
and presented in terms of supramolecular chemistry and
crystal engineering concepts.
3
O
O
2
N
HO
4
7
Phenylurea/AcOH
heat, 15 Minutes
OH
OH
5
1NH
OH
8
6
O
O
Ninhydrin
1
Phenylthiourea/AcOH
heat, 15 Minutes
3
N
S
2
HO
4
7
2. Experimental
1NH
OH
5
8
6
2.1 Instrument and chemicals
O
Ninhydrin, 1-phenylurea and 1-phenylthiourea were
purchased from Aldrich (Germany) and used as
received. Chloroform, ethanol and glacial acetic acid
were obtained from Merck (Germany) and used with-
out further purification. All other reagents used were
of analytical grade. The melting points were taken
on Thermo Fisher digital melting point apparatus of
IA9000 series and are uncorrected. FTIR spectra were
measured by direct transmittance by means of the KBr
pellet technique using a Nicolet Impact 400 FTIR
spectrometer equipped with a DTGS detector. High
resolution ESI-MS were recorded on a Finnigan TSQ
Quantum Ultra AM Thermo Electron. 1H NMR spectra
were recorded on Bruker Avance 500 MHz with TMS
as an internal standard and 125 MHz for 13C NMR.
Spectra were recorded in DMSO-d6. Elemental ana-
lysis was performed on a Perkin Elmer 2400 Series II
Elemental CHNS analyzer.
2
Scheme 1. Synthetic route for derivatives 1 and 2.
844, 763, 729, 693, 653 cm−1. H NMR (DMSO-d6,
500 MHz): δ 3.40 (br s, 1 H, N–H), 7.02 (br s, 1 H,
–O–H), 6.80–7.83 (m, 9H, Aromatic), 8.55 (br s, 1
H, –O–H) ppm (Figure S1 in Supplementary Informa-
tion). 13C NMR (DMSO-d6, 125 MHz): δ 85.2, 90.1,
123.8, 124.8, 126.5, 128.1 (2C), 128.4 (2C), 130.4,
132.3, 135.9, 136.1, 149.2, 154.7 (C=O), 197.5 (C=O)
ppm (Figure S2 in SI). HR ESI (MS): m/z 297.1341
[M+H]+, 12.6%; 296.0368 [M]+, 61%. Elemental anal.
Calcd. (%) for C16H12N2O4: C, 64.86; H, 4.08; N, 9.46;
O, 21.60. Found (%): C, 64.73; H, 4.05; N, 9.41; O,
21.51.
1
2.3 Synthesis of 3a,8a-Dihydroxy-1-phenyl-2-thioxo-2,
3,3a,8a-tetrahydro-1H-indeno[1,2-d]imidazol-8-one (2)
2.2 Synthesis of 3a,8a-Dihydroxy-1-phenyl-1,3,3a,8a-
tetrahydro-indeno[1,2-d]imidazole-2,8-dione (1)
Compound 2 was synthesized by following above-
mentioned method except that phenylthiourea (1.52 g)
A mixture of ninhydrin (1.78 g) and phenylurea (1.36 g) was used in place of phenylurea (Scheme 1). The reac-
in molar ratio 1:1 were well-dissolved in acetic acid tion mixture was dried by using rotary evaporator at
and then heated at 100◦C over water bath for 15 min. low pressure to give the solid product which was then
The solvent was removed by using rotary evaporator recrystallized from alcohol-chloroform (1:1 v/v) mix-
at low pressure to give the solid product, which was ture to give transparent crystals of the title compound
then crystallized from ethanol–chloroform (1:1 v/v) 2 (Scheme 1). Yield: 95%, M.p. 256–268◦C. IR (KBr):
mixture to give the translucent crystals of title com- νmax 3582, 3408, 3051, 2000, 1963, 1732, 1600, 1459,
pound (Scheme 1). Yield: 95%, M.p. 215–217◦C. IR 1212, 1112, 1019, 968, 927, 902, 809, 749, 729, 711,
(KBr): νmax 3481, 3260, 3062, 1961, 1722, 1685, 1596, 697, 658 cm−1. 1H NMR (DMSO-d6, 500 MHz): δ 3.40
1495, 1422, 1290, 1211, 1178, 1135, 1055, 932, 905, (br s, 1 H, N–H), 6.69–7.96 (m, 9H, aromatic), 10.13

A facile approach for indenoimidazoles
(br s, 1 H, –O–H), 10.38 (br s, 1 H, –O–H) ppm titled compounds 1 and 2 have been deposited with
(Figure S3). 13C NMR (DMSO-d6, 125 MHz): δ 88.4, the Cambridge Structural Data Centre (CCDC) with
92.2, 123.8, 125.2, 127.2, 128.2 (2C), 130.9 (2C), reference numbers (1042090, 1042091). The crystallo-
132.4, 136.4, 137.1, 148.5, 150.6, 178.6 (C=S), 195.3 graphic parameters of crystal structure of 1 and 2 are
(C=O) ppm (Figure S4). HR ESI (MS): m/z 313.1242 presented in Table 1.
[M+H]+, 12.3%; 312.0459 [M]+, 60.9%. Elemental
anal. Calcd (%) for C16H12N2O3S: C, 61.53; H, 3.87; N,
2.5 Refinement special details
8.97; O, 15.37; S, 10.27. Found (%): C, 61.46; H, 3.69;
Refinement of F2 was performed against all reflections.
The weighted R-factor (wR) and goodness of fit S are
based on F2, conventional R-factor (R) are based on F,
with F set to zero for negative F2. The threshold expres-
sion of F2 >2sigma(F2) is used only for calculating
R-factors (gt), etc., and is not relevant to the choice of
reflections for refinement. R-factors based on F2 are sta-
tistically about twice as large as those based on F, and
R-factors based on all data will be even larger.
N, 8.83; O, 15.34; S, 10.19.
2.4 Crystal structure determination
Reflection data were measured at 293 K with a
Bruker APEX2 CCD diffractometer in θ/2θ scan mode
using graphite monochromated molybdenum radiation
(λ 0.7107 A◦). SMART was used for collecting frame
data, indexing reflection, and determination of lat-
tice parameters.35 SAINT was used for integration of
intensity of reflections and scaling.35 A semi-empirical
absorption correction was applied using the program
SADABS.36 The structure was solved by direct meth-
ods using the program SHELXS.37 The refinement
and all further calculations were carried out using
3. Results and Discussion
3.1 Structural Study of 3a,8a-Dihydroxy-1-phenyl-1,3,
3a,8a-tetrahydro-indeno[1,2-d]imidazole-2,8-dione (1)
the program SHELXL.37 The H-atoms were included X-ray quality crystals of compound 1 were obtained
in calculated positions and treated as riding atoms by direct crystallization of 1 from ethanol–chloroform
using SHELXL default parameters. The non-H atoms (1:1 v/v) solvent mixture. Slow evaporation of the sol-
were refined anisotropically, using weighted full-matrix vent has led to nice block-colorless crystals. Compound
least-squares on F2. Crystallographic data (cif) of the 1 crystallizes in the monoclinic space group P21/c
Table 1. Numerical details of the solution and refinement of the crystal structures
of compounds 1 and 2.
Compound
1
2
Formula
Formula mass
Space group
a/Å
C16H12N2O4
296.28
(C16H12N2O3S).(H2O)
330.35
P21/c
P21/c
12.0913(7)
5.7204(3)
19.8168(11)
90
103.6650(10)
90
11.0101(5)
6.8421(3)
21.1243(9)
90
110.771(2)
90
b/Å
c/Å
α/◦◦
γ/
β/◦
V/Å3
1331.87(13)
293(2)
1487.91(11)
293(2)
T/Kꢁ
Z, Z
4,0
4,0
F000
616
1.478
MoKα, 0.7107
θ/2θ
3.04–32.61
I/σ(I) >2
0.0457
688
1.475
MoKα, 0.7107
θ/2θ
1.98–36.78
I/σ(I) >2
0.0471
Dcalc./g cm−3
Radiation, λ/Å
Scan mode
2θμmin − 2θμmax
◦
/
Criterion for obs. ref.
ꢀ
ꢀ
m
m
R =
|ꢀF|/
|Fo|
ꢁ
ꢂ
ꢀ
ꢀ
1/2
m
m
2
2
Rw =
w|ꢀF| /
w|Fo|
0.1240
1.034
0.1347
1.056
ꢁ
ꢂ
ꢀ
1/2
m
2
s =
w|ꢀF| /(m − n)

Raza Murad Ghalib et al.
with four molecules in the asymmetric unit. Labeled bond. Centrosymmetric dimer is formed between two
molecules of 1 in which oxygen atom (O4) of the cyclic
ketone carbonyl group of one molecule is bifurcating
with the hydrogen atoms of the two hydroxyl groups of
another molecule of 1 (H1O3 and H1O2) with a con-
tact distances of 1.874 Å and 2.234 Å, respectively as
shown in Figure 2.
molecular structure of 1 including thermal displacement
ellipses (50% probability) is shown in Figure 1.
Molecular structure of 1 contains two different types
of carbonyl groups; cyclic amide (lactam) and aro-
matic cyclic ketone. Both groups are totally different in
terms of bond length, strength, and angle. Shorter and
stronger carbon-oxygen double bond (C3-O1=1.209 Å
and C2-C3-C4 bond angle of 108.04◦) is detected for
the cyclic ketone compared to the cyclic amide (C1-
O4=1.240 Å and N1-C1-N2 bond angle of 109.04◦).
Strong intermolecular non-covalent interactions are
observed between molecules of 1 such as hydrogen
´
´
Another edge-edge motif interaction is observed in
the crystal packing of 1, in which two molecules are
interacting through O4 and H1N2 of each molecule to
form hydrogen-bonded centrosymmetric dimer with a
´
contact distance of 2.161 Å as shown in Figure 3.
In addition to the above two centrosymmetric dimers,
strong hydrogen bonds are connected between two
Figure 3. Edge-edge hydrogen-bonded centrosymmetric
dimer of two molecules of 1 with a contact distance of
2.161 Å.
Figure 1. Molecular structure of 1. Thermal ellipsoids are
presented in 50% probability.
´
Figure 4. Hydrogen-bonded centrosymmetric dimer
between two molecules of 1 with a contact distance of
1.874 Å.
Figure 2. Strong hydrogen bonding which led to cen-
trosymmetric dimer constructed from two molecules of 1.
´

A facile approach for indenoimidazoles
molecules of 1 to produce a centrosymmetric dimer displacement ellipses (50% probability) is shown in
through the interactions between H1O3 and O4 with
Figure 5. In addition, the asymmetric unit contains four
molecules of 2 and four water molecules as shown in
Figure 6.
´
a contact distance of 1.874 Å (Figure 4). Other types
of intermolecular non-covalent interactions such as,
´
Normally, any slight change in the molecular struc-
ture of a given solid compound will lead to a great
change in its supramolecular behavior. In our case, the
only difference in the molecular structure between 1
and 2 is that sulfur atom is replaced by oxygen atom
of the carbonyl group of the cyclic amide (lactam)
to produce a thia-lactam derivative. This replacement
has forced compound 2 to include water molecules
into its crystal structure to form a host-guest complex
(hydrate). Crystal structure analyses of compound 2
revealed that longer and weaker carbon-oxygen double
nitrogen-nitrogen (3.443 Å), nitrogen-hydrogen (2.993
´
´
Å), nitrogen-oxygen (2.972 Å), and oxygen-oxygen
´
(2.808 Å) were observed and proved to have strong
influence on crystal packing of compound 1.
3.2 Structural Study of 3a,8a-Dihydroxy-1-phenyl-2-
thioxo-2,3,3a,8a-tetrahydro-1H-indeno[1,2-d]imidazol-
8-one (2)
X-ray quality crystals of compound were obtained by
direct crystallization of 2 from, ethanol–chloroform
(1:1 v/v) solvent mixture. Slow evaporation of the sol-
vent has led to nice plates of colorless crystals. Com-
pound 2 crystallizes in the monoclinic space group
P21/c to produce a hydrated crystal structure with a
molecular formula of (C16H12N2O3S).(H2O). Labeled
´
bond (C2-O1=1.223 Å and C1-C2-C3 bond angle of
107.99◦) exists in the molecular structure of 2 compared
to 1. As expected, lactam carbon-sulfur double bond
´
has longer and weaker bond (C10-S1=1.673 Å and
N1-C10-N2 bond angle of 108.74◦) than the lactam
hydrated molecular structure of 2 including thermal carbon-oxygen double bond of 1. Different types of
Figure 5. ORTEP plot of the hydrated crystal structure of compound 2 showing 50% probability ellipsoids.
Figure 6. The asymmetric unit of 2. Four molecules of the titled compound together with four water molecules.

Raza Murad Ghalib et al.
Figure 7. Two molecules of 2 interact through sulfur-hydrogen interaction to produce centrosymmetric dimer.
bridges two molecules of 2 by acting as hydrogen-bond
donor and acceptor at the same time. Oxygen atom
of one water molecule (O1W) is strongly hydrogen-
bonded to an acidic hydrogen of 2 (H1O2) with a
´
contact distance of 1.797 Å. In the same structure,
hydrogen atom of the same water molecule (H1W1)
is strongly hydrogen-bonded to an oxygen atom of
another molecule of 2 (O2) with a contact distance of
´
1.807 Å as shown in Figure 8. Weaker intermolecu-
lar non-covalent interactions are existed in the crys-
tal structure of the hydrated form of 2 such as, S. . .S
´
´
´
(4.495 Å), S. . .N (3.346 Å), S. . .O (4.4 and 4.36 Å),
´
´
´
N. . .N (4.093 Å), N. . .H (3.443 Å), N. . .O (3.782 Å),
´
and O. . .O (2.789 Å).
4. Conclusions
Figure 8. Water molecule acts as both hydrogen bond
donor and acceptor as bridge between two molecules of 2.
Solid-state crystal structures of compounds 1 and 2
were successfully determined, analyzed and presented
in terms of crystal engineering and supramolecular
chemistry. Any slight change in the molecular structure
of any given solid compound will lead to a great change
in its supramolecularity. In this paper, we replaced oxy-
gen atom of compound 1 by sulfur atom to produce
compound 2. This replacement forced compound 2 to
include water molecules and formed the hydrated form.
Different types of intermolecular non-covalent interac-
strong intermolecular non-covalent interactions were
observed in the crystal structure of the hydrated form
of 2. Sulfur atom of the lactam part of one molecule
(S1) is interacting with hydrogen atom attached to
the nitrogen atom of the lactam part of another molecule
(H1N2) to produce a centrosymmetric dimer with a
´
contact distance of 2.505 Å (Figure 7).
Water molecules play an important role in stabilizing tions were observed and compared for both 1 and 2. It is
the crystal packing of 2 due to its strong ability to form still very difficult to predict the crystal structure and the
a hydrogen bond with both hydrogen-bond donor and supramolecular behavior even if we know the molecu-
acceptor. In the crystal structure of 2, water molecule lar structure. More work need to done in this area to

A facile approach for indenoimidazoles
13. Anderson S, Anderson H L, Bashall A, McPartlin M
enhance our knowledge and to increase the possibi-
lity to predict at least a little bit of the supramolecular
behavior of a solid compound in its crystalline form.
and Sanders J K M 1995 Angew Chem. Int. Ed. 34
1096
14. Freeman W A 1984 Acta Cryst. Sect. B 40 382
15. Schmitt J-L, Stadler A-M, Kyritsakas N and Lehn J-M
2003 Helv. Chim. Acta 86 1598
Supplementary Information (SI)
16. Lehn J-M 1993 Science 260 1762
17. Lehn J-M 1995 In Supramolecular Chemistry (Wein-
heim: Wiley-VCH Verlag GmbH)
18. Gennady V, Oshovsky David N R and Willem V 2007
Angew. Chem. Int. Ed. 46 2366
19. Alshahateet S F, Bishop R, Craig D C and Scudder M L
2011 Cryst. Growth Des. 11 4474
20. Ghalib R M, Hashim R, Alshahateet S F, Mehdi S H,
Sulaiman O, Chan K-L, Murugaiyah V and Jawad A
2012 J. Chem. Crystallogr. 42 783
21. MacNicol D D and Downing G R 1996 In Sym-
metry in the evolution of host design, in Compre-
hensive Supramolecular Chemistry, Vol. 6 Solid-state
Supramolecular Chemistry: Crystal Engineering D
MacNicol, F Toda and R Bishop (Eds.) (Oxford: Perga-
mon Press) Ch. 14 pp. 421–464
Scanned copies of 1H and 13C spectra of 1 and
2 are given in electronic Supporting Information
available at www.ias.ac.in/chemsci. CCDC-1042090
and 1042091 contain the supplementary crystallo-
graphic data for 1 and 2. This data can be obtained
free of charge at http://www.ccdc.cam.ac.uk/conts/
retrieving.html [or from the Cambridge Crystallo-
graphic Data Centre (CCDC), 12 Union Road, Cam-
bridge CB2 1EZ, UK; fax: +44(0)1223-336033; email:
deposit@ccdc.cam.ac.uk].
22. Ghalib R M, Hashim R, Alshahateet S F, Mehdi S H,
Sulaiman O, Murugaiyah V and Aruldass C A 2011 J.
Mol. Struct. 1005 152
23. Alshahateet S F, Al-Zereini W A and Alghezawi N M
2011 J. Chem. Crystallogr. 41 1807
24. Kooli F, Hian P C, Weirong Q, Alshahateet S F and
Chen F 2006 J. Porous Mat. 13 319
Acknowledgements
Authors would like to acknowledge University of Jed-
dah, KSA and Universiti Sains Malaysia (USM) for the
research facilities.
25. Alshahateet S F, Bishop R, Craig D C and Scudder M L
2003 CrystEngComm 3 417
26. Alshahateet S F, Bishop R, Craig D C and Scudder M L
2010 Cryst. Growth Des. 10 1842
27. Alshahateet S F, Bishop R, Scudder M L, Hu C Y, Lau
E H E, Kooli F, Judeh Z M A, Chow P S and Tan R B H
2005 CrystEngComm 7 139
28. Kooli F, Mainhui L, Alshahateet S F, Chen F and
Yinghuai Z 2006 J. Phys. Chem. Solids 67 926
29. Alshahateet S F, Bishop R, Craig D C, Kooli F and
Scudder M L 2008 CrystEngComm 10 297
30. Alshahateet S F, Ong T T, Bishop R, Kooli and Messali
M 2006 Cryst. Growth Des. 6 1676
31. Alshahateet S F, Bishop R, Craig D C, Scudder M L and
Ung A T 2001 Struct. Chem. 12 251
32. Alshahateet S F, Bhadbhade M M, Bishop R and
Scudder M L 2015 CrystEngComm 17 877
33. Alshahateet S F, Bhadbhade M M, Bishop R, Craig D C
and Scudder M L 2015 CrystEngComm 17 9111
34. Alshahateet S F 2015 Mol. Cryst. Liq. Cryst. 607 169
35. SMART and SAINT 1996 Software Reference Manu-
als Version 4.0 (Siemens Energy and Automation, Inc.,
Analytical Instrumentation: Madison, WI)
36. Sheldrick G M 1996 In SADABS (Germany: University
of Göttingen)
37. Sheldrick G M 2008 SHELXS and SHELXL Acta Crys-
tallogr. A 64 112
References
1. Roberts L R, Bryans J, Conlon K, McMurray G, Stobie
A and Whitlock G A 2008 Bioorg. Med. Chem. Lett. 18
6437
2. Sarra J D and Stephani R A 2000 Med. Chem. Res. 10 81
3. Chen W, Yang L-J, Li Y, Wang X-Q, Wang S-J, Wan
W-C, Zhang H-B and Yang X-D 2013 Lett. Drug Des.
Discov. 10 561
4. Sarkarzadeh H, Miri R, Firuzi O, Amini M, Razzaghi-
Asl N, Edraki N and Shafiee A 2013 Arch. Pharm. Res.
36 436
5. Devi T U, Priya S, Selvanayagam S, Ravikumar K
and Anitha K 2012 Spectrochim. Acta Mol. Biomol.
Spectros. 97 1063
6. Shapiro R and Chatterjie N 1970 J. Org. Chem. 35 447
7. Hossaini Z, Seyfi S, Rostami-Charati F and Ghambarian
M 2013 Comb. Chem. High T. Scr. 16 788
8. Chatterjie N, Sinha B and Alexander G J 1983 Res.
Commun. Chem. Pathol. Pharmacol. 39 333
9. Ghalib R M, Hashim R, Mehdi S H, Quah C K and Fun
H-K 2011 Acta Cryst. E 67 o1525
10. Hasenknopf B, Lehn J-M, Kneisel B O, Baum G and
Fenske D 1996 Angew Chem. Int. Ed. 35 1838
11. Day A I 2002 Angew. Chem. Int. Ed. 41 275
12. Bravo J A 1998 Eur. J. Org. Chem. 1998 2565