Hydrogen-bonded structures from adamantane-based catechols

Article abstract of DOI:10.1016/j.molstruc.2018.03.011

Adamantane-based bis- and tris-catechols were synthesized to examine the effect of hydrogen bonds on the arrangement and packing of the components in the crystalline state. Single-crystal X-ray crystallographic analysis revealed that hydrogen bonds formed

Full text of DOI:10.1016/j.molstruc.2018.03.011

Journal of Molecular Structure 1164 (2018) 116e122
Contents lists available at ScienceDirect
Journal of Molecular Structure
journal homepage: http://www.elsevier.com/locate/molstruc
Hydrogen-bonded structures from adamantane-based catechols
,
,
Masatoshi Kawahata a *, Miku Matsuura a, Masahide Tominaga a **, Kosuke Katagiri b,
,
***
Kentaro Yamaguchi a
a Faculty of Pharmaceutical Sciences at Kagawa Campus, Tokushima Bunri University, 1314-1 Shido, Sanuki, Kagawa 769-2193, Japan
b Department of Chemistry, Faculty of Science and Engineering, Konan University, 8-9-1 Okamoto, Higashinada-ku, Kobe, Hyogo 658-8501, Japan
a r t i c l e i n f o
a b s t r a c t
Article history:
Adamantane-based bis- and tris-catechols were synthesized to examine the effect of hydrogen bonds on
the arrangement and packing of the components in the crystalline state. Single-crystal X-ray crystallo-
graphic analysis revealed that hydrogen bonds formed by the hydroxyl groups of catechol groups play
essential roles in the production of various types of unique structures. 1,3-Bis(3,4-dihydroxyphenyl)
adamantane (1) provided hydrogen-bonded network structures composed of helical chains in crystal
from chloroform/methanol, and layer structures in crystal from ethyl acetate/hexane. The complexation
of 1 with 1,3,5-trinitrobenzene or 1,2,4,5-tetracyanobenzene resulted in the formation of co-crystals,
respectively. One-dimensional hydrogen-bonded structures were constructed from the adamantane-
based molecules, which participated in charge-transfer interactions with guests. 1,3,5-Tris(3,4-
dihydroxyphenyl)adamantane also afforded crystal, and the components were assembled into infinite
polymers.
Received 10 November 2017
Received in revised form
1 March 2018
Accepted 5 March 2018
Available online 14 March 2018
Keywords:
Supramolecular chemistry
Molecular recognition
Crystal structure
Hydrogen bond
Charge-transfer interaction
© 2018 Published by Elsevier B.V.
1. Introduction
broadly utilized as a scaffold for the preparation of supramolecular
materials [32,33]. Several catechol-containing molecules were
Catechol and its derivatives have elicited much attention in the
areas of material science, supramolecular chemistry, and bio-
mimetic chemistry [1‒4] because they are easily available and
useful key units for the development of polymers that contribute to
the adhesion property of mussels [5‒8], as well as porous network
polymers and covalent organic frameworks for the adsorption and
inclusion of gas and small molecules [9‒13]. Catechol-containing
molecules have been exploited as ligands for the construction of
discrete metal-mediated complexes [14‒19] and as building blocks
for functional molecules with boronate esters [20‒24] and spi-
roborates [25e28]. Compounds possessing two catechol moieties
include 3,3ʹ,4,4ʹ-tetrahydroxybiphenyl, 2,2ʹ,3,3ʹ-tetrahydroxy-1,1ʹ-
designed by connecting spacer parts and catechol groups. The
spacer units used were phenylene, diethynylphenylene, azo-
benzene, and others [34e39].
In crystal engineering, diverse hydrogen-bonded crystalline
materials are created by utilizing the multiple hydrogen bonds of
hydroxyl groups in phenol-containing molecules [40e43]. In
contrast, reports of the preparation of crystalline materials from
catechol-containing molecules are rare.
Previously, we described the synthesis and structure analysis of
a series of adamantane-based molecules having phenol derivatives,
which were used in the generation of hydrogen-bonded crystalline
solids with cavities and channels where solvents and small organic
molecules were accommodated [44e48].
binaphthyl,
5,5ʹ,6,6ʹ-tetrahydroxy-3,3,3ʹ,3ʹ-tetramethyl-1,1ʹ-spi-
robisindane, and dimethyl tetrahydroxytriptycene [29e31]. Cyclo-
tricatechylene, a cyclic trimer composed of catechol groups linked
by methylene groups, is a cyclic compound and its derivatives are
Adamantane has a symmetrical and spherical skeleton with
aliphatic characteristics. Therefore, adamantane-based molecules
possessing
a few catechol groups may provide fascinating
hydrogen-bonded network structures that show inclusion ability
for small organic molecules in the crystalline state.
In this work, we report the preparation and the crystal struc-
tures of 1,3-bis(3,4-dihydroxyphenyl)adamantane (1) and 1,3,5-
tris(3,4-dihydroxyphenyl)adamantane (2). The disubstituted ada-
mantane compound having catechol groups yielded two kinds of
* Corresponding author.
** Corresponding author.
*** Corresponding author.
E-mail addresses: kawahatam@kph.bunri-u.ac.jp (M. Kawahata), tominagam@
kph.bunri-u.ac.jp (M. Tominaga), kyamaguchi@kph.bunri-u.ac.jp (K. Yamaguchi).
https://doi.org/10.1016/j.molstruc.2018.03.011
0022-2860/© 2018 Published by Elsevier B.V.

M. Kawahata et al. / Journal of Molecular Structure 1164 (2018) 116e122
117
crystals depending on the recrystallization solvent, namely, a
mixture of chloroform and methanol or ethyl acetate and hexane,
where hydrogen-bonded network structures made up of helical
chains or layer structures consisting of cyclic frameworks were
formed, respectively. Further, the co-crystallization of 1 with 1,3,5-
trinitrobenzene (3) or 1,2,4,5-tetracyanobenzene (4) as guest mol-
ecules in methanol or a mixture of water and ethanol resulted in
the formation of charge-transfer co-crystals where their network
structures were different from that of the crystal structures without
the guest molecules. The trisubstituted adamantane compound
gave one-dimensional (1D) polymers consisting of cyclic frame-
works from methanol.
methanol solution of the resulting solids afforded the title com-
pound as a white solid (3.05 g, 8.65 mmol) in 72% yield. M.p.
210e211 ꢀC. FT-IR (ATR, cmꢁ1): 3499, 2913, 2846, 1603, 1520, 1464,
1326, 1266, 1190, 1106, 943, 940, 916, 866, 797, 783. 1H NMR
(400 MHz, DMSO-d6)
d
8.61 (s, 2H), 8.57 (s, 2H), 6.76 (d, J ¼ 2.0 Hz,
2H), 6.65 (d, J ¼ 8.4 Hz, 2H), 6.60 (dd, J ¼ 8.4, 2.0 Hz, 2H), 2.18 (br s,
2H), 1.77 (br d, J ¼ 2.8 Hz, 10H), 1.69 (br s, 2H). 13C NMR (100 MHz,
DMSO-d6) d 144.6, 142.8, 141.8, 115.13, 115.06, 112.3, 49.2, 42.1, 35.9,
35.4, 29.0. HRMS (ESI, m/z) Calcd for C22H23O4 [M ꢁ H]ꢁ 351.1602,
found 351.1606.
2.3. 1,3,5-Tris(3,4-dihydroxyphenyl)adamantane (2)
The title compound was synthesized in 42% yield as a white
solid in a manner similar to the preparation of 1,3-bis(3,4-
dihydroxyphenyl)adamantane (1), where 1,3,5-adamantanetriol
was used instead of 1,3-adamantanediol. M.p. 271e272 ꢀC. FT-IR
(ATR, cmꢁ1): 3312, 2897, 2847, 1602, 1517, 1430, 1340, 1255, 1193,
2. Experimental section
2.1. General
All reagents and solvents were obtained from commercial sup-
pliers and used as received. Melting points were determined using
an ATM-01. IR spectra were recorded on a Jasco FT/IR-6300. 1H and
13C NMR spectra were recorded on a Bruker AV400 spectrometer at
298 K in DMSO-d6 with tetramethylsilane as reference. X-ray crystal
structure data were collected using a Bruker D8 VENTURE diffrac-
1108, 942, 870, 807, 782. 1H NMR (400 MHz, DMSO-d6)
d
8.65 (br s,
6H), 6.86 (s, 3H), 6.72 (s, 6H), 2.41 (br s, 1H) 1.85 (br d, J ¼ 7.6 Hz,
12H). 13C NMR (100 MHz, DMSO-d6)
144.5, 142.8, 141.4, 115.2,
d
115.1, 112.4, 48.3, 41.2, 36.9, 29.6. HRMS (ESI, m/z) Calcd for
C
28H27O6 [MꢁH]ꢁ 459.1813, found 459.1821.
tometer with Cu Ka radiation. Column chromatography was per-
formed on a Wakogel C200, and thin-layer chromatography was
carried out on 2.0-mm Merck precoated silica gel glass plates. High-
resolution mass spectrometric measurements were carried out on
an Exactive (Thermo Fisher Scientific) consisting of an Orbitrap
analyzer and an electrospray ionization (ESI) source.
2.4. Crystallization
Crystal 1a was obtained from the slow evaporation of a
chloroform-methanol mixture of 1. Co-crystal 1b was obtained
from the vapor diffusion of hexane into an ethyl acetate solution of
1. Co-crystals 1c and 1d were generated from the slow evaporation
of a methanol solution of 1 with 1,3,5-trinitrobenzene (3) or a
mixture of water and ethanol of 1 with 1,2,4,5-tetracyanobenzene
(4) in a 1:1 ratio. Co-crystal 2a was formed from the slow evapo-
ration of a methanol solution of 2.
Caution! 1,3,5-Trinitrobenzene is highly explosive and should be
handled carefully even in small amounts.
2.2. 1,3-Bis(3,4-dihydroxyphenyl)adamantane (1)
A mixture of 1,3-adamantanediol (2.02 g, 12.0 mmol) and cate-
chol (3.96 g, 36.0 mmol) in methanesulfonic acid (10 mL) was stir-
red at 80 ꢀC for 3 h under an argon atmosphere. After cooling to
room temperature, the reaction mixture was poured into ice water
and then added to ethyl acetate. The organic layers were separated
and the aqueous layer was extracted with ethyl acetate. The com-
bined organic layers were washed with water, brine, and dried over
sodium sulfate. The filtrate was evaporated under reduced pressure
and the residue was purified by silica gel column chromatography
(eluent: chloroform:methanol ¼ 10:1, v/v). Recrystallization from a
2.5. Single-crystal X-ray crystallography
The diffraction experiment was performed on a Bruker D8
VENTURE system (PHOTON-100 CMOS detector, CuKa:
l
¼ 1.54178 Å). Absorption correction was performed by an empir-
ical method implemented in SADABS [49]. Structure solution and
refinement were performed by using SHELXT-2014/5 [50] and
SHELXL-2016/6 [51]. Summarized crystal data are shown in Table 1.
CCDC
1555041e1555045
contain
the
supplementary
Table 1
Crystal data for the five crystals.
Crystal
1a
1b
1c
1d
2a
Chemical Formula
Formula weight
Recryst. Solvent
Crystal system
Space group
a (Å)
C22H24O4
352.41
CHCl3/MeOH
monoclinic
P21/c
10.9394(8)
10.8640(8)
14.4447(10)
90.00
91.965(2)
90.00
C24H28O5
396.46
n-Hexane/AcOEt
triclinic
C34H30N6O16
778.64
MeOH
orthorhombic
Pbcn
28.177(4)
12.7023(18)
9.1916(13)
90.00
90.00
90.00
3289.8(8)
4
1.572
C32H31.35N4O6.68
578.85
EtOH/Water
triclinic
C29.74H34.98O7.74
516.36
MeOH
triclinic
P-1
9.8257(10)
9.9510(11)
13.0464(14)
79.263(3)
76.480(2)
86.219(3)
1218.2(2)
2
P-1
P-1
6.4112(13)
12.948(3)
13.432(3)
63.383(5)
79.063(5)
84.763(5)
978.7(3)
2
6.4290(7)
13.6973(16)
14.0150(16)
81.905(3)
78.031(3)
79.259(3)
1179.5(2)
2
b (Å)
c (Å)
a
b
g
(ꢀ)
(ꢀ)
(ꢀ)
V (Å3)
1715.7(2)
4
1.364
Z
Dcalc (Mg/m3)
T (K)
1.345
100
1.379
100
1.408
100
100
100
R1, wR2 [I > 2
R1, wR2 (all data)
CCDC No.
s
(I)]
0.0513, 0.2015
0.0549, 0.2026
1555041
0.0368, 0.1018
0.0386, 0.1035
1555042
0.0415, 0.1188
0.0468, 0.1209
1555043
0.0409, 0.1101
0.0441, 0.1134
1555044
0.0821, 0.2057
0.0832, 0.2067
1555045

118
M. Kawahata et al. / Journal of Molecular Structure 1164 (2018) 116e122
Table 3
Geometrical Parameters of 2 in Co-crystal 2a.
Crystal
2a
Torsion Angle (deg)
C1eC2eC3eC4
C4eC5eC6eC7
C8eC9eC10eC11
Dihedral Angle (deg)
P1eP2
ꢁ62.5
176.8
ꢁ62.6
75.9
66.9
69.1
Scheme 1. Synthesis of Two Adamantane-Based Molecules with Catechol Groups.
P2eP3
P3eP1
crystallographic data. These data can be obtained free of charge via
www.ccdc.cam.ac.uk/data_request/cif, or by emailing data_
request@ccdc.cam.ac.uk, or by contacting The Cambridge Crystal-
lographic Data Center, 12 Union Road, Cambridge CB2 1EZ, UK;
fax: þ44 1223 336033.
3. Results and discussion
We synthesized adamantane-based molecules (1, 2) by per-
forming the coupling reaction of catechol and 1,3-adamantanediol
or 1,3,5-adamantanetriol in methanesulfonic acid in 72 and 42%
yields, respectively (Scheme 1). Both compounds were character-
ized by 1H and 13C NMR spectroscopy and high-resolution mass
spectrometry. Crystal data and conformational parameters of all the
crystals are indicated in Fig.1 and Tables 1e3. Two or three catechol
rings in 1 or 2 of all crystals exhibited a bent and twisted confor-
mation (Fig. 1). The torsion angles between specific CeC bonds of
adamantane units and CeC bonds of the catechol units in the
formed crystals and co-crystals are shown in Tables 2 and 3 These
values range from ꢁ117.6e177.4ꢀ.
Fig. 1. Thermal ellipsoidal models (50% probability) of the crystal structures of
adamantane-based catechols. (a) Crystal 1a, (b) co-crystal 1b, (c) co-crystal 1c, (d) co-
crystal 1d, and (e) co-crystal 2a. Solvent, guest molecules, and some disordered atoms
are omitted for charity.
Crystal 1a crystallized in the monoclinic system and the space
group P21/c, and included one molecule of 1 in the asymmetric unit.
Molecule 1 is assembled into helical chains with one pitch of two
Table 2
Geometrical parameters of 1 in crystal 1a and Co-crystal 1be1d.
Crystal
1a
1b
1c
1d
Torsion Angle (deg)
C1eC2eC3eC4
C4eC5eC6eC7
Dihedral Angle (deg)
P1eP2
177.4
80.9
ꢁ58.6
ꢁ73.0
ꢁ117.6
ꢁ117.6
ꢁ66.8
ꢁ54.4
84.3
86.5
89.3
84.2

M. Kawahata et al. / Journal of Molecular Structure 1164 (2018) 116e122
119
molecules of 1 via hydrogen bonds between the hydroxyl groups in
the catechol groups, where the distance between the oxygen atoms
is 2.67 Å (Fig. 2a). In single helical chains, the centroidꢁcentroid
distance between adamantane parts is 10.86 Å. Further, one of the
planes of the catechol rings is parallel and the other is perpendic-
ular to the axis of the helical structures. The helical chains form
layers and their network structures through the hydrogen bonds
between the hydroxyl groups, where the distances between the
oxygen atoms are 2.77e2.85 Å (Fig. 2b and c).
Co-crystal 1b crystallized in the triclinic system and the space
group P-1, and included one molecule of 1 and one molecule of
ethyl acetate in the asymmetric unit. The cyclic structures are
constructed from two molecules of 1 through the hydrogen bonds
between the hydroxyl groups (the distance between the oxygen
atoms is 2.81 Å), where the centroidꢁcentroid distance between
the adamantane parts is 11.42 Å (Fig. 3b and c). The cyclic frame-
works are extended along the c axis via the hydrogen bonds be-
tween the hydroxyl groups (the distance between the oxygen
atoms is 2.85 Å), resulting in the formation of 1D structures. 1D
polymers consisting of cyclic frameworks are directed into the
layers through the hydrogen bonds between the hydroxyl groups
(the distance between the oxygen atoms is 2.71 Å, Fig. 3a). Thus,
there are channels in the crystalline lattices, which are filled with
Fig. 3. Packing diagram of 1 in co-crystal 1b. (a) Side and (b) top views of network
structures. (c) Top view of network structures in a space-filling model. Hydrogen bonds
are indicated by red dotted lines. Solvent molecules are omitted for clarity. (For
interpretation of the references to color in this figure legend, the reader is referred to
the Web version of this article.)
Fig. 2. Packing diagram of 1 in crystal 1a. (a) Layer structures composed of helical
chains from the side view. (b) Top and (c) side views of network structures. Hydrogen
bonds are indicated by red dotted lines. (For interpretation of the references to color in
this figure legend, the reader is referred to the Web version of this article.)

120
M. Kawahata et al. / Journal of Molecular Structure 1164 (2018) 116e122
Fig. 4. Packing diagram of 1 and 3 in co-crystal 1c. (a) Top and (b) side views of the
network structures. Hydrogen bonds are indicated by red dotted lines. (For interpre-
tation of the references to color in this figure legend, the reader is referred to the Web
version of this article.)
Fig. 5. Packing diagram of 1 and 4 in co-crystal 1d. (a) Top and (b) side views of
network structures. Hydrogen bonds are indicated by red dotted lines. Solvent mole-
cules are omitted for clarity. (For interpretation of the references to color in this figure
legend, the reader is referred to the Web version of this article.)
ethyl acetate. Individual layers are assembled into the network
structures via CH$$$p interactions between the catechol rings and
the adamantane parts, where the distance between the carbon
atoms of adamantane units and the center of catechol rings is
3.83 Å.
The catechol group is electron-rich and thus its derivatives can
interact with electron-deficient molecules as an acceptor to form
complexes through charge-transfer interactions, which display
signature color in the visible region. Therefore, we examined the
trinitrobenzene (3) as the representative acceptor molecule
[52e59]. Reddish brown co-crystals 1c were considerably different
in color from both components in the solid state. Co-crystal 1c
crystallized in the orthorhombic system and the space group Pbcn,
and included a half molecule of 1 and one molecule of 3 in the
asymmetric unit. Therefore, the arrangement of 1 was notably
changed in the presence of the guest molecule. Molecule 1 is
preparation of charge-transfer co-crystals from
1 and 1,3,5-

M. Kawahata et al. / Journal of Molecular Structure 1164 (2018) 116e122
121
assembled into 1D polymers consisting of cyclic frameworks
derived from two molecules of 1 via the hydrogen bonds between
the hydroxyl groups along the c axis, where the distance between
the oxygen atoms of them is 2.96 Å (Fig. 4 and S3). In a single
polymer, the centroidꢁcentroid distance between adamantane
parts is 9.49 Å. Further, hydrogen bonds between the hydroxyl
groups of the catechol groups and the oxygen atoms of 3 were
observed, and the distance between the oxygen atoms was 2.89 Å.
The catechol groups in the components also interacted with guest
molecules via charge-transfer interactions to form the network
structures (the centroidꢁcentroid distance of aromatic rings and
the dihedral angle between the planes of aromatic rings are 3.66 Å
and 11.3ꢀ, respectively).
Another acceptor molecule for the development of organic
charge-transfer complexes, 1,2,4,5-tetracyanobenzene (4) [60,61],
was also utilized. Similarly, reddish brown co-crystals 1d were
obtained. Co-crystal 1d crystallized in the triclinic system and the
space group P-1, and included one molecule of 1, a half molecule of
4, and three molecules of water in the asymmetric unit. Molecule 1
is directed into infinite polymers via the hydrogen bonds between
the hydroxyl groups along the c axis, where the distance between
the oxygen atoms is 2.72 Å (Fig. 5b). One catechol group in the
components interacts with 4 via charge-transfer interactions to
form the layer structures (the centroidꢁcentroid distance of aro-
matic rings and the dihedral angle between the planes of aromatic
rings are 3.84 Å and 13.3ꢀ, respectively). Further, the oxygen atoms
of the catechol groups interact with the hydrogen atoms of 4
through CH/O interactions (the distance between the oxygen
atom and the carbon atom is 3.28 Å), resulting in the generation of
network structures. Additionally, CH$$$p interactions between the
catechol rings and adamantane parts (the distances between the
carbon atoms of adamantane parts and the center of catechol rings
are 3.90 and 3.91 Å) were observed. The guest molecules are ar-
ranged in a 1D array along the a axis in the crystalline state (Fig. 5a).
Co-crystal 2a consisting of tripodal molecule 2 crystallized in
the triclinic system and the space group P-1, and included one
molecule of 2 and three molecules of methanol in the asymmetric
unit. Two molecules of 2 are assembled into the cyclic structures
and these structures are induced into infinite polymers via the
hydrogen bonds between the hydroxyl groups. The distances be-
tween the oxygen atoms are 2.77 and 2.82 Å (Fig. 6). The 1D
structures are guided into the network structures through the
multiple hydrogen bonds between the catechol groups. Methanol
molecules binding with catechol groups via hydrogen bonds were
observed in the crystalline lattices.
4. Conclusion
In conclusion, we have designed adamantane-based bis- and
tris-catechols as novel key compounds for the construction of the
hydrogen-bonded organic frameworks of helical chains, polymers,
layers, and network structures in the solid state. Adamantane-
based catechols bearing electron-rich parts interact with 1,3,5-
trinitrobenzene or 1,2,4,5-tetracyanobenzene as electron-acceptor
guest molecules via charge-transfer interactions, generating co-
crystals. Therefore, adamantane-based bis- and tris-catechols are
versatile building blocks and supramolecular synthons for crystal
engineering and solid-state chemistry. The synthesis of
adamantane-based molecules having other phenol derivatives,
such as resorcinol, hydroquinone, and pyrogallol, and their struc-
tural analysis and applications are under investigation.
Acknowledgements
This work was partly supported by JSPS KAKENHI Grant Number
JP16K05801 and JP16K08214. HRMS measurement was performed
at the Center for Analytical Instrumentation, Chiba University.
Appendix A. Supplementary data
Supplementary data related to this article can be found at
https://doi.org/10.1016/j.molstruc.2018.03.011.
References
Fig. 6. Packing diagram of 2 in co-crystal 2a. (a) Top and (b) side views of 1D polymers
composed of cyclic structures. Hydrogen bonds are indicated by red dotted lines.
Solvent molecules are omitted for clarity. (For interpretation of the references to color
in this figure legend, the reader is referred to the Web version of this article.)
[1] J.H. Waite, Ann. N. Y. Acad. Sci. 875 (1999) 301e309.
[2] N.B. McKeown, P.M. Budd, K.J. Msayib, B.S. Ghanem, H.J. Kingston,
C.E. Tattershall, S. Makhseed, K.J. Reynolds, D. Fritsch, Chem. Eur. J. 11 (2005)

122
M. Kawahata et al. / Journal of Molecular Structure 1164 (2018) 116e122
223e230.
2610e2620.
[3] R. Nishiyabu, Y. Kubo, T.D. James, J.S. Fossey, Chem. Commun. 47 (2011)
1124e1150.
[4] X. Feng, X. Ding, D. Jiang, Chem. Soc. Rev. 41 (2012) 6010e6022.
[5] M. Yu, T.J. Deming, Macromolecules 31 (1998) 4739e4745.
[6] M.J. Harrington, A. Masic, N. Holten-Andersen, J.H. Waite, P. Fratzl, Science 328
(2010) 216e220.
[31] N.G. White, M.J. MacLachlan, Chem. Sci. 6 (2015) 6245e6249.
[32] M.J. Hardie, Chem. Soc. Rev. 39 (2010) 516e527.
[33] J.A. Hyatt, E.N. Duesler, D.Y. Curtin, I.C. Paul, J. Org. Chem. 45 (1980)
5074e5079.
[34] A. Caneschi, A. Dei, H. Lee, D.A. Shultz, L. Sorace, Inorg. Chem. 40 (2001)
408e411.
[7] D. Ling, W. Park, Y.I. Park, N. Lee, F. Li, C. Song, S.G. Yang, S.H. Choi, K. Na,
T. Hyeon, Angew. Chem. Int. Ed. 50 (2011) 11360e11365.
[8] H. Xu, J. Nishida, W. Ma, H. Wu, M. Kobayashi, H. Otsuka, A. Takahara, ACS
Macro Lett. 1 (2012) 457e460.
[35] M.K. Smith, N.E. Powers-Riggs, B.H. Northrop, Chem. Commun. 49 (2013)
6167e6169.
[36] M. Yamamura, Y. Okazaki, T. Nabeshima, Chem. Commun. 48 (2012)
5724e5726.
[9] N.B. McKeown, S. Hanif, K. Msayib, C.E. Tattershall, P.M. Budd, Chem. Com-
mun. (2002) 2782e2783.
[37] S. Greatorex, M.A. Halcrow, CrystEngComm 18 (2016) 4695e4698.
[38] R. Sekiya, Y. Yamasaki, S. Katayama, H. Shio, T. Haino, CrystEngComm 13
(2013) 8404e8407.
[10] B.S. Ghanem, K.J. Msayib, N.B. McKeown, K.D.M. Harris, Z. Pan, P.M. Budd,
A. Butler, J. Selbie, D. Book, A. Walton, Chem. Commun. (2007) 67e69.
[11] S. Makhseed, J. Samuel, Chem. Commun. (2008) 4342e4344.
[12] M. Mastalerz, Angew. Chem. Int. Ed. 47 (2008) 445e447.
[13] J. Jiang, Y. Zhao, O.M. Yaghi, J. Am. Chem. Soc. 138 (2016) 3255e3265.
[14] B.F. Abrahams, N.J. FitzGerald, R. Robson, Angew. Chem. Int. Ed. 46 (2007)
8640e8643.
[39] P. Satha, G. Illa, C.S. Purohit, Cryst. Growth Des. 13 (2013) 2636e2641.
[40] R.J. Sarma, J.B. Baruah, Cryst. Growth Des. 7 (2007) 989e1000.
[41] B.K. Saha, S. Bhattacharya, CrystEngComm 12 (2010) 2369e2373.
ꢀ
[42] S. Aitipamula, P.K. Thallapally, R. Thaimattam, M. Jaskolski, G.R. Desiraju, Org.
Lett. 4 (2002) 921e924.
[43] S. Aitipamula, G.R. Desiraju, M. Jaskolski, A. Nangia, R. Thaimattam, Crys-
ꢀ
[15] B.F. Abrahams, N.J. FitzGerald, R. Robson, Inorg. Chem. 49 (2010) 5953e5956.
[16] B.F. Abrahams, B.A. Boughton, N.J. FitzGerald, J.L. Holmes, R. Robson, Chem.
Commun. 47 (2011) 7404e7406.
[17] M. Albrecht, I. Janser, R. Frohlich, Chem. Commun. (2005) 157e165.
[18] M.D. Pluth, R.G. Bergman, K.N. Raymond, Acc. Chem. Res. 42 (2009)
1650e1659.
[19] C.J. Brown, F.D. Toste, R.G. Bergman, K.N. Raymond, Chem. Rev. 115 (2015)
3012e3035.
[20] N. Nishimura, K. Kobayashi, Angew. Chem. Int. Ed. 47 (2008) 6255e6258.
[21] K. Kataoka, S. Okuyama, T. Minami, T.D. James, Y. Kubo, Chem. Commun.
(2009) 1682e1684.
tEngComm 5 (2003) 447e450.
[44] M. Tominaga, K. Katagiri, I. Azumaya, Cryst. Growth Des. 9 (2009) 3692e3696.
[45] M. Tominaga, K. Katagiri, I. Azumaya, CrystEngComm 12 (2010) 1164e1170.
[46] M. Tominaga, H. Masu, I. Azumaya, Cryst. Growth Des. 11 (2011) 542e546.
[47] M. Tominaga, H. Masu, I. Azumaya, CrystEngComm 13 (2011) 5299e5302.
[48] H. Masu, M. Tominaga, I. Azumaya, Cryst. Growth Des. 13 (2013) 752e758.
€
€
[49] G.M. Sheldrick, SADABS, University of Gottingen, Germany, 1996.
[50] G.M. Sheldrick, Acta Crystallogr. A71 (2015) 3e8.
[51] G.M. Sheldrick, Acta Crystallogr. C71 (2015) 3e8.
[52] K. Biradha, A. Nangia, G.R. Desiraju, C.J. Carrell, H.L. Carrell, J. Mater. Chem. 7
(1997) 1111e1122.
[22] K. Severin, Dalton Trans. (2009) 5254e5264.
[23] B. Icli, E. Solari, B. Kilbas, R. Scopelliti, K. Severin, Chem. Eur. J. 18 (2012)
14867e14874.
[53] P.K. Thallapally, A.K. Katz, H.L. Carrell, G.R. Desiraju, CrystEngComm 5 (2003)
87e92.
[54] R.K.R. Jetti, R. Boese, P.K. Thallapally, G.R. Desiraju, Cryst. Growth Des. 3 (2003)
1033e1040.
[55] P.K. Thallapally, R.K.R. Jetti, A.K. Katz, H.L. Carrell, K. Singh, K. Lahiri, S. Kotha,
R. Boese, G.R. Desiraju, Angew. Chem. Int. Ed. 43 (2004) 1149e1155.
[24] A. Wilson, G. Gasparini, S. Matile, Chem. Soc. Rev. 43 (2014) 1948e1962.
[25] B.F. Abrahams, D.J. Price, R. Robson, Angew. Chem. Int. Ed. 45 (2006) 806e810.
[26] H. Danjo, K. Hirata, S. Yoshigai, I. Azumaya, K. Yamaguchi, J. Am. Chem. Soc.
131 (2009) 1638e1639.
[27] H. Danjo, K. Hirata, M. Noda, S. Uchiyama, K. Fukui, M. Kawahata, I. Azumaya,
K. Yamaguchi, T. Miyazawa, J. Am. Chem. Soc. 132 (2010) 15556e15568.
[28] H. Danjo, Y. Hashimoto, Y. Kidena, A. Nogamine, K. Katagiri, M. Kawahata,
T. Miyazawa, K. Yamaguchi, Org. Lett. 17 (2015) 2154e2157.
[29] J. Best, I.V. Sazanovich, H. Adams, R.D. Bennett, E.S. Davies, A.J.H.M. Meijer,
M. Towrie, S.A. Tikhomirov, O.V. Bouganov, M.D. Ward, J.A. Weinstein, Inorg.
Chem. 49 (2010) 10041e10056.
ꢀ~
ꢀ
[56] Y. Salinas, R. Martínez-Manez, M.D. Marcos, F. Sancenon, A.M. Costero,
M. Parra, S. Gil, Chem. Soc. Rev. 41 (2012) 1261e1296.
[57] A. Das, S. Ghosh, Angew. Chem. Int. Ed. 53 (2014) 2038e2054.
[58] Z. Hu, B.J. Deibert, J. Li, Chem. Soc. Rev. 43 (2014) 5815e5840.
[59] X. Sun, Y. Wang, Y. Lei, Chem. Soc. Rev. 44 (2015) 8019e8061.
[60] R.O. Al-Kaysi, A.M. Müller, R.J. Frisbee, C.J. Bardeen, Cryst. Growth Des. 9
(2009) 1780e1785.
[61] A. Khan, M. Wang, R. Usman, H. Sun, M. Du, C. Xu, Cryst. Growth Des. 17
(2017) 1251e1257.
[30] J.A. Bjork, M.L. Brostrom, D.R. Whitcomb, J. Chem. Crystallogr. 27 (1997)