Hydrogen-Bonded 1D Chains Formed from Adamantane-Based

Article pubs.acs.org/crystal

Hydrogen-Bonded 1D Chains Formed from Adamantane-Based Bisphenols and Bispyridines: Influences of Substitution Groups on Phenol Ring Hyuma Masu,‡ Masahide Tominaga,*,† and Isao Azumaya*,† †

Faculty of Pharmaceutical Sciences at Kagawa Campus, Tokushima Bunri University, 1314-1 Shido, Sanuki, Kagawa 769-2193, Japan Chemical Analysis Center, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, Japan

‡

S Supporting Information *

ABSTRACT: Eight cocrystals were formed from three adamantane-based bisphenols with structurally analogous skeletons and three bispyridines. Various 1D chains were constructed through intermolecular OH/N hydrogen bonds. Two crystals containing nonsubstituted bisphenols showed the formation of 1D zigzag chains, which were generated from two bisphenols and two bispyridines in one pitch of the 1D chain. Three crystals including chlorine-substituted bisphenols indicated the generation of 1D zigzag chains, and the pitches of these chains were longer than that of 1D chains composed of nonsubstituted bisphenols. Three crystals containing bromine-substituted bisphenols exhibited different shapes of 1D chains from other crystals, which were consisted of one bisphenol and one bispyridine in one pitch. These 1D chains assembled via intermolecular CH/O and/or CH/π interactions. The halogen substituents on the adamantane-based bisphenols influence on not only the shapes of 1D chains, but also 2D and 3D structures mainly due to steric hindrances.

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INTRODUCTION One-dimensional polymeric chains are simple and basic structures in organic crystals. They can assemble into more highly-ordered two- and three-dimensional molecular networks. A variety of 1D chains including linear, zigzag, and helical structures have been produced from diverse organic molecules with noncovalent bonds between each component of a 1D chain and cooperative interactions between each 1D chain.1,2 In the field of crystal engineering,3 the rational and precise design of 1D chains is important for predicting molecular packing and association of individual components in the solid states.4−7 However, the examples systematically examined for the creation of 1D chains by a series of structurally related organic components concerning molecular shapes, steric hindrances, and modes of weak interactions have been restricted to date. Adamantane-based molecules bearing various functional groups are versatile candidates for the component of the infinite 1D chains because of their rigid skeleton and geometrically directional interactions sites.8 Recently, we have demonstrated that several adamantane-based bisphenols construct various organic networks involving channels and cavities via hydrogen bonds between phenol groups.9 The adamantane-based bisphenols composed of ortho-substituted phenol groups and a bulky adamantane spacer have two V-directional hydrogenbonding sites. Thus, we applied a series of the adamantane-based bisphenols to generate the 1D polymeric chains to investigate effects of shapes and bulkiness of component molecules on the © XXXX American Chemical Society

association and alignment of the 1D chains in the crystalline state. Several 1D chains composed of various adamantane-based molecules such as 1,3-adamantanedicarboxylic acid, 1,3adamantanediacetic acid, and 1,3-bis(4-hydroxyphenyl)adamantane with bispyridine derivatives and N-oxide compounds in cocrystals have been reported.8b,e Thus, we utilized a cocrystallization method to generate the 1D chains10 and chose bispyridine derivatives as partners with the bisphenols. The combination of the components is well-known as supramolecular synthons, and provides predictable assemblies and solids due to directional and strong hydrogen bonding.11,12 Various halogen atoms were used as the ortho-substituents of the bisphenols. The comparison of crystal structures between a set of cocrystals built from the analogical components should aid to understand the effect of shapes and bulkiness of the components. Here we report on the design and structural analysis of eight cocrystals involving diverse 1D chains by the crystallization of the adamantane-based bisphenols, 1,3-bis(4-hydroxyphenyl)adamantane (1), 1,3-bis(3chloro-4-hydroxyphenyl)adamantane (2), 1,3-bis(3-bromo-4hydroxyphenyl)adamantane (3), and bispyridine derivatives, 4,4′-bipyridine (a), 1,2-bis(4-pyridyl)ethane (b), and 1,2-di(4pyridyl)ethylene (c) (Chart 1). Single crystals suitable for diffraction analysis were obtained by the slow evaporation of an Received: October 6, 2012 Revised: December 18, 2012

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dx.doi.org/10.1021/cg301462v | Cryst. Growth Des. XXXX, XXX, XXX−XXX

Crystal Growth & Design

Article

room temperature, colorless single crystals of 1a−b, 2a−c, and 3a−c were obtained by slow evaporation of the solvent after a week. Measurement. Single crystal X-ray diffraction data of the crystals were collected on a Bruker ApexII CCD diffractometer with graphite monochromated Mo Kα (λ = 0.71073 Å) radiation. Data collections were carried out at low temperature (100−200 K) using liquid nitrogen. The crystal structure was solved by direct methods SHELXS-97 and refined by full-matrix least-squares SHELXL-97.14 All non-hydrogen atoms were anisotropically refined. Positions of hydrogen atoms were calculated based on geometrical adequacy. The geometrical parameters for hydrogen bonds (Tables S1−S8 of the Supporting Information, SI) are calculated by PLATON program.15 Crystal data are shown in Table 1.

Chart 1. Adamantane-Based Bisphenols and Bispyridines

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ethanol solution of 1−3 and a−c at a ratio of 1:1, respectively. Xray diffraction experiments evidenced the formation of various types of 1D chains via intermolecular OH/N hydrogen bonds for cocrystals 1a, 1b, 1c,13 2a, 2b, 2c, 3a, 3b, and 3c.

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RESULTS AND DISCUSSION In all of the crystals, the adamantane-based bisphenols connect to the bispyridine derivatives alternately through OH/N hydrogen bonds between the hydroxy groups of the phenol moieties and the nitrogen atoms of the bispyridines at a ratio of 1:1 (Tables S1−8 in Supporting Information). Thus, they form the 1D chain structures. Two phenyl rings in bisphenols 1−3 of all crystals showed a bent and twist conformation (Figure 1). Dihedral angles between two phenyl planes are about 63−89° (φ1 in Table 2). Moreover,

EXPERIMENTAL SECTION

Preparation of Compounds. Adamantane-based bisphenols 1−3 were synthesized by previous reported manner.9b Bispyridine derivatives a−c were used from commercial reagents. Crystallization. A mixture of bisphenols (0.1 mmol) and bispyridines (0.1 mmol) in ethanol (10.0 mL) were stirred for 1 h at

Table 1. Crystal Data for the Measured Eight Co-Crystals crystal

1a

1b

2a

2b

formula formula weight crystal system space group a (Å) b (Å) c (Å) α (°) β (°) γ (°) V (Å3) Z Dcalc (Mg/m3) T (K) R1, wR2 [I > 2σ(I)] R1, wR2 (all data) CCDC No. crystal

C22H24O2·C10H8N2 476.60 orthorhombic Pca21 12.076(3) 6.3815(16) 32.010(8) 90.00 90.00 90.00 2466.9(11) 4 1.283 150 0.0317, 0.0726 0.0372, 0.0760 904318 2c

C22H24O2·C12H12N2 504.65 orthorhombic Pbcn 6.2857(19) 12.624(4) 32.881(10) 90.00 90.00 90.00 2609.2(14) 4 1.285 120 0.0395, 0.1023 0.0468, 0.1074 904319 3a

C22H22O2Cl2·C10H8N2 545.48 monoclinic P21/c 9.893(12) 7.770(9) 35.39(4) 90.00 96.781(13) 90.00 2701(5) 4 1.341 200 0.0703, 0.2301 0.1028, 0.2833 904320 3b

C22H22O2Cl2·C12H12N2 573.53 monoclinic C2/c 7.7044(15) 11.564(2) 32.152(7) 90.00 96.560(2) 90.00 2845.9(10) 4 1.339 200 0.0390, 0.1005 0.0444, 0.1042 904321 3c

formula formula weight crystal system space group a (Å) b (Å) c (Å) α (°) β (°) γ (°) V (Å3) Z Dcalc (Mg/m3) T (K) R1, wR2 [I > 2s(I)] R1, wR2 (all data) CCDC No.

C22H22O2Cl2·C12H10N2 571.52 monoclinic C2/c 7.6272(14) 11.462(2) 32.491(6) 90.00 96.602(2) 90.00 2821.7(9) 4 1.345 200 0.0331, 0.0843 0.0413, 0.0893 904322

C22H22O2Br2·C10H8N2 634.40 monoclinic P21/c 19.233(2) 7.2860(10) 21.471(2) 90.00 116.647(8) 90.00 2689.2(5) 4 1.567 200 0.0309, 0.0695 0.0477, 0.0758 904323 B

C22H22O2Br2·C12H12N2·O 678.45 triclinic P-1 9.6666(14) 10.5148(15) 16.003(2) 79.171(2) 82.682(2) 73.440(2) 1526.6(4) 2 1.476 200 0.0303, 0.0784 0.0368, 0.0820 904324

C22H22O2Br2·C12H10N2 660.44 monoclinic Cc 33.810(13) 11.423(4) 7.647(3) 90.00 101.221(4) 90.00 2897(2) 4 1.514 120 0.0355, 0.0882 0.0383, 0.0898 904325



Article

Figure 1. Crystal structures of the cocrystals. (a) Crystal 1a, (b) crystal 1b, (c) crystal 1c,8b (d) crystal 2a, (e) crystal 2b, (f) crystal 2c, (g) crystal 3a, (h) crystal 3b, and (i) crystal 3c. Included solvent molecules or disordered atoms were omitted for clarity.

Table 2. Geometrical Parameters of the Co-Crystals

1a 1b 1c8b 2a 2b 2c 3a 3b 3c

θ1 (deg)

θ2 (deg)

φ1 (deg)

φ2 (deg)

61.3(2) 56.05(12) 55.92(14) 9.7(4) 119.03(14) 59.65(15) 62.2(3) 4.1(3) 56.9(8)

63.4(2) 56.05(12) 55.92(14) 68.9(4) 119.03(14) 59.65(15) −68.0(3) 61.9(2) 59.8(9)

81.76(8) 71.56(10) 73.58(7) 77.43(16) 89.10(8) 88.90(7) 85.31(12) 63.40(11) 87.3(3)

27.71(9) 0.00 0.00 31.9(2) 0.00 0.00 31.76(13) 41.77(15) 5.1(4)

in the crystals 1b, 1c, 2b, and 2c, two torsion angles of bonds between the phenyl ring and the adamantane core (θ1 and θ2 in Table 2) are equivalent and have same direction of twist (rightor left-hand). It means that the adamantane-based bisphenols have proper C2 symmetry. This symmetry is related to the conformations of each bispyridine derivative. In these crystals, two pyridine planes of the b or c are parallel (φ2 in Table 2). Other crystals have lower symmetry, where the pyridine planes are not parallel. Thus, it suggested that the twist of bispyridine derivatives influences on the twist conformations of the bisphenols. The crystals 1a and 1b indicated orthorhombic crystal lattices with a Pca21 space group for 1a and a Pbcn space group for 1b. In intermolecular hydrogen bonds, the distances of the O···N atoms are about 2.72 and 2.76 Å for 1a and 2.77 Å for 1b. In the crystal 1a, the twist (asymmetric) bisphenol components and twist a components construct a helical 1D chain structure along the c axis (Figure 2a). A pitch of the helix is about 32.0 Å and generated from two bisphenols and two bispyridines. The shape of the helix

Figure 2. Crystal structure of 1a. (a) A hydrogen-bonded 1D chain from front view and side view. (b) A view along the a axis of the chains. (c) A packing structure from a view along the b axis. Some molecular chains are colored in cyan for clarity. Hydrogen bonds are indicated by black dotted lines.

is considerably flat. The helical 1D chains line up along the b axis and form a layer structure (Figure 2b), which assembled into a 3D network structure in the crystal along the a axis via CH/O interactions (the distance of the C···O atoms between bispyridine and phenol group was 3.30 Å) and CH/π interactions (the distances between the carbon atoms of the bispyridine and the ring centers of the phenol groups were 3.66 and 3.67 Å) C



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(Figure 2c). Neighbor layers are formed from the opposite helixes each other. Thus, the crystal structure of 1a is achiral. However, each 1D chains in the crystal 1b are constructed with right- and left-handed twist bisphenols 1 and b. As a result, the 1D chain is not helix but zigzag structure (Figure 3a). A pitch of

Figure 4. Crystal structure of 2a. (a) A hydrogen-bonded 1D chain from front view and side view. (b) A view along the a axis of the chains. (c) A packing structure from a view along the b axis.

the b axis and form a layer structure via CH/π interactions (the distance between the carbon atom and the ring center of the bispyridine was 3.67 Å) (Figure 4b), which aggregate in the crystal along the a axis (Figure 4c). The crystal structures of 2b and 2c were mostly similar each other (Figures 5 and 6). The pitches of these zigzag 1D chains are

Figure 3. Crystal structure of 1b. (a) A hydrogen-bonded 1D chain from front view and side view. (b) A view along the b axis of the chains. (c) A packing structure from a view along the a axis.

the 1D chain is about 35.2 Å for 1b. However, a trend of layerstacking in the crystal 1b is similar to that in 1a (Figure 3b,c). Intermolecular CH/π interactions (the distance between the carbon atom of the bispyridine and the ring center of the phenol group was 3.44 Å) was also observed in the crystal 1b. The crystal structure of 1c is very similar to that of 1b.8b Crystal 2a−c showed monoclinic crystal lattices with a P21/c space group for 2a and C2/c space groups for 2b and 2c. In intermolecular hydrogen bonds, the distances of the O···N atoms were about 2.72 and 2.73 Å for 2a, 2.68 Å for 2b, and 2.68 Å for 2c. The effect of substituents on the bisphenol for the structures of the 1D chains was shown in crystal 2a−c. Because of the steric hindrances of chlorine substituents, the dihedral angles between two phenyl planes of the bisphenol 2 were relatively large (about 77−89°, φ1 in Table 2). It causes an expanding of the pitch and shrinking of the width in the 1D chains as shown in the crystal structure of 2a (Figure 4a). A pitch of the 1D chain is about 42.5 Å for 2a in contrast to about 32.0 Å for 1a. Although the conformations of each component were similar to 1a, the 1D chains in 2a had a zigzag structure. The 1D chains line up along

Figure 5. Crystal structure of 2b. (a) A hydrogen-bonded 1D chain from front view and side view. (b) A view along the c axis of the chains. (c) A packing structure from a view along the a axis. D



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Figure 7. Crystal structure of 3a. (a) One pair of two hydrogen-bonded 1D chains from front view and side view. (b) A view along the c axis of the chains. (c) A packing structure from a view along the b axis. Some molecular chains are colored in cyan or magenta for clarity.

Figure 6. Crystal structure of 2c. (a) A hydrogen-bonded 1D chain from front view and side view. (b) A view along the c axis of the chains. (c) A packing structure from a view along the a axis.

structure mainly through CH/O interactions (the distance of the C···O atoms between bispyridine and phenol group was 3.41 Å) (Figure 8b), which aggregate along the b axis (Figure 8c). It is expected that bulky substituents allow a void space in the crystals. Actually, a channel structure including water molecules was formed in crystal 3b (Figure 8c). In the crystalline lattices, a pair of two opposing 1D chains having a long pitch provided a channel-shaped structure along the a axis. Alternatively, crystal 3c had a packing structure unlike crystals 3a and 3b. The hydrogen-bonded 1D chain exhibited a 1D zigzag structure with a pitch of about 24.1 Å similar to that of crystal 3b (Figure 9a). However, the void space including solvent molecules was not constructed. The 1D chains line up along the b axis and form a layer via CH/π interactions (the distances between the carbon atoms of the bispyridine or phenol groups and the ring center of the phenol group was 3.62 and 3.56 Å), which aggregate alternately to fill each of the void spaces (Figure 9b,c). In this work, we succeeded in the construction of eight cocrystals by the combination of three adamantane-based bisphenol molecules bearing different ortho-substituents on the phenol ring and three bispyridine derivatives. The hydroxy groups of phenol moieties interacted with nitrogen atoms of the bispyridine derivatives due to intermolecular hydrogen bonds to direct into infinite 1D chains in all crystals. The substituents on the bisphenols play a significant role in producing a wide variety of 1D chains, 2D, and 3D aggregation due to steric hindrances mainly. Studies on the production of 2D and 3D hydrogenbonded networks built from tri- and tetra-substituted adamantanes bearing functionalized phenol parts and the bispyridine derivatives are under investigation.

very close and much long than that of 2a and corresponding 1b, c (Figures 5a and 6a). The pitches of the 1D chains are about 47.3 Å for 2b and 47.2 Å for 2c. The 1D chains form a 2D layer along the ac plane, which are tightly arranged along the b axis mainly through CH/O interactions (the distances of the C···O atoms between bispyridines and phenol groups are 3.51 Å for 2b and 2c) (Figures 5b, 5c, 6b, and 6c). Crystals 3a and 3c indicated monoclinic crystal lattices with a P21/c space group for 3a and a Cc space group for 3c. Crystal 3b showed a triclinic crystal lattice with a P-1 space group. In intermolecular hydrogen bonds, the distances of the O···N atoms were about 2.70 and 2.72 Å for 3a, 2.67 and 2.70 Å for 3b, 2.72 and 2.80 Å for 3c. The bromine substituents of the bisphenols gave rise to more large change of the crystal structures relative to non- and chlorine-substituted bisphenols. The symmetries of the bisphenol 3 and bispyridine components were reduced (Table 2). The hydrogen-bonded 1D chain in crystal 3a exhibited a different zigzag structure from that in crystals 1a−c and 2a−c. A pitch of the 1D chain is about 21.5 Å and generated from one bisphenol and one bispyridine (Figure 7a). The 1D chains line up along the b axis and form a layer structure (Figure 7b), which provided network structures along the c axis through CH/O interactions (the distances of the C···O atoms between bispyridines and phenol groups were 3.39−3.51 Å) and CH/π interactions (the distances between the carbon atoms of the bispyridine and the ring centers of the phenol groups were 3.61 Å) (Figure 7c). Crystal 3b indicated the formation of 1D zigzag chains with a pitch of about 24.3 Å in common with that of crystal 3a (Figure 8a). The 1D chains line up along the a axis and form a layer E



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Figure 8. Crystal structure of 3b. (a) One pair of two hydrogen-bonded 1D chains f from front view and side view. (b) A view along the b axis of the chains. (c) A packing structure containing water molecules from a view along the a axis. Some molecular chains are colored in cyan or magenta for clarity. Hydrogen atoms of the water molecules are not indicated.

Figure 9. Crystal structure of 3c. (a) A hydrogen-bonded 1D chain from front view and side view. (b) A view along the c axis of the chains. (c) A packing structure from a view along the b axis.

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Shimon, L. J. W.; Gupta, T.; Martin, J. M. L.; van der Boom, M. E. Cryst. Growth Des. 2008, 8, 3066−3072. (d) Du, M.; Zhang, Z.-H.; Guo, W.; Fu, X.-J. Cryst. Growth Des. 2009, 9, 1655−1657. (e) Perkins, C.; Libri, S.; Adams, H.; Brammer, L. CrystEngComm 2012, 14, 3033−3038. (2) (a) Yue, W.; Bishop, R.; Craig, D. C.; Scudder, M. L. CrystEngComm 2002, 4, 591−595. (b) Muthu, S.; Vittal, J. J. Cryst. Growth Des. 2004, 4, 1181−1184. (c) Lü, J.; Han, L.-W.; Lin, J.-X.; Liu, T.-F.; Cao, R. Cryst. Growth Des. 2010, 10, 4217−4220. (d) Hisaki, I.; Shizuki, N.; Sasaki, T.; Ito, Y.; Tohnai, N.; Miyata, M. Cryst. Growth Des. 2010, 10, 5262−5269. (e) Sun, D.; Li, Y.-H.; Hao, H.-J.; Liu, F.-J.; Wen, Y.-M.; Huang, R.-B.; Zheng, L.-S. Cryst. Growth Des. 2011, 11, 3323− 3327. (3) (a) Desiraju, G. R. Angew. Chem., Int. Ed. 1995, 34, 2311−2327. (b) Sommerdijk, N. A. J. M. Angew. Chem., Int. Ed. 2003, 42, 3572− 3574. (c) Braga, D.; Desiraju, G. R.; Miller, J. S.; Orpen, A. G.; Price, S. L. CrystEngComm 2002, 4, 500−509. (d) Moulton, B.; Zaworotko, M. J. Chem. Rev. 2001, 101, 1629−1658. (e) Sarma, R. J.; Baruah, J. B. Cryst. Growth Des. 2007, 7, 989−1000. (4) (a) Metrangolo, P.; Neukirch, H.; Pilati, T.; Resnati, G. Acc. Chem. Res. 2005, 38, 386−395. (b) Morimoto, M.; Irie, M. Chem.−Eur. J. 2006, 12, 4275−4282. (c) Shirota, Y.; Kageyama, H. Chem. Rev. 2007, 107, 953−1010. (d) Ye, Q.; You, X.; Zou, G.; Yu, X.; Zhang, Q. J. Mater. Chem. 2008, 18, 2775−2780. (e) Cariati, E.; Cavallo, G.; Forni, A.; Leem, G.; Metrangolo, P.; Meyer, F.; Pilati, T.; Resnati, G.; Righetto, S.; Terraneo, G.; Tordin, E. Cryst. Growth Des. 2011, 11, 5642−5648.

ASSOCIATED CONTENT

S Supporting Information *

The crystallographic data and crystallographic information files (CIF) for crystals 1a−b, 2a−c, and 3a−c. This material is available free of charge via the Internet at http://pubs.acs.org.

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AUTHOR INFORMATION

Corresponding Author

*Tel: +81-87-894-5111 ext. 6305; fax: +81-87-894-0181; e-mail: [email protected] (M.T.), [email protected]. ac.jp (I.A.). Notes

The authors declare no competing financial interest.

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ACKNOWLEDGMENTS This work was supported by a Grant-in-Aid for Scientific Research (C) Grant Number 23590002 from Japan Society for the Promotion of Science (JSPS).

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REFERENCES

(1) (a) Aakeröy, C. B.; Desper, J.; Leonard, B.; Urbina, J. F. Cryst. Growth Des. 2005, 5, 865−877. (b) Han, B.; Lu, J.; Kochi, J. K. Cryst. Growth Des. 2008, 8, 1327−1334. (c) Shirman, T.; Lamere, J.-F.; F



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(5) (a) Matsumoto, A.; Tanaka, T.; Tsubouchi, T.; Tashiro, K.; Saragai, S.; Nakamoto, S. J. Am. Chem. Soc. 2002, 124, 8891−8902. (b) Hoang, T.; Lauher, J. W.; Fowler, F. W. J. Am. Chem. Soc. 2002, 124, 10656− 10657. (c) Takahashi, S.; Miura, H.; Kasai, H.; Okada, S.; Oikawa, H.; Nakanishi, H. J. Am. Chem. Soc. 2002, 124, 10944−10945. (d) Gao, X.; Frišcǐ ć, T.; MacGillivray, L. R. Angew. Chem., Int. Ed. 2004, 43, 232−236. (e) Nomura, S.; Itoh, T.; Nakasho, H.; Uno, T.; Kubo, M.; Sada, K.; Inoue, K.; Miyata, M. J. Am. Chem. Soc. 2004, 126, 2035−2041. (f) Itoh, T.; Suzuki, T.; Uno, T.; Kubo, M.; Tohnai, N.; Miyata, M. Angew. Chem., Int. Ed. 2011, 50, 2253−2256. (6) (a) Sozzani, P.; Bracco, S.; Comotti, A.; Ferretti, L.; Simonutti, R. Angew. Chem., Int. Ed. 2005, 44, 1816−1820. (b) Afonso, R. V.; Durão, J.; Mendes, A.; Damas, A. M.; Gales, L. Angew. Chem., Int. Ed. 2010, 49, 3034−3036. (c) Rajput, L.; Chernyshev, V. V.; Biradha, K. Chem. Commun. 2010, 6530−6532. (d) He, Y.; Xiang, S.; Chen, B. J. Am. Chem. Soc. 2011, 133, 14570−14573. (e) Mastalerz, M.; Oppel, I. M. Angew. Chem., Int. Ed. 2012, 51, 5252−5255. (7) (a) Sozzani, P.; Comotti, A.; Bracco, S.; Simonutti, R. Angew. Chem., Int. Ed. 2004, 43, 2792−2797. (b) Frišcǐ ć, T.; Lancaster, R. W.; Fábián, L.; Karamertzanis, P. G. Proc. Natl. Acad. Sci. U.S.A. 2010, 107, 13216−13221. (c) Hisaki, I.; Murai, T.; Yabuguchi, H.; Shigemitsu, H.; Tohnai, N.; Miyata, M. Cryst. Growth Des. 2011, 11, 4652−4659. (d) Hinoue, T.; Miyata, M.; Hisaki, I.; Tohnai, N. Angew. Chem., Int. Ed. 2012, 51, 155−158. (8) (a) Fleischman, S. G.; Kuduva, S. S.; McMahon, J. A.; Moulton, B.; Bailey Walsh, R. D.; Rodríguez-Hornedo, N.; Zaworotko, M. J. Cryst. Growth Des. 2003, 5, 909−919. (b) Zeng, Q.; Wu, D.; Ma, H.; Shu, C.; Li, Y.; Wang, C. CrystEngComm 2006, 8, 189−201. (c) Men, Y.-B.; Sun, J.; Huang, Z.-T.; Zheng, Q.-Y. Angew. Chem., Int. Ed. 2009, 48, 2873− 2876. (d) Men, Y.-B.; Sun, J.; Huang, Z.-T.; Zheng, Q.-Y. Chem. Commun. 2010, 6299−6301. (e) Manjare, Y.; Pedireddi, V. R. Cryst. Growth Des. 2011, 11, 5079−5086. (9) (a) Tominaga, M.; Katagiri, K.; Azymaya, I. Cryst. Growth Des. 2009, 9, 3692−3696. (b) Tominaga, M.; Masu, H.; Azymaya, I. Cryst. Growth Des. 2011, 11, 542−546. (10) (a) Ma, B.-Q.; Coppens, P. Chem. Commun. 2003, 2290−2291. (b) Remenar, J. F.; Morissette, S. L.; Peterson, M. L.; Moulton, B.; MacPhee, J. M.; Guzman, H. R.; Almarsson, Ö . J. Am. Chem. Soc. 2003, 125, 8456−8457. (c) Sada, K.; Inoue, K.; Tanaka, T.; Epergyes, A.; Tanaka, A.; Tohnai, N.; Matsumoto, A.; Miyata, M. Angew. Chem., Int. Ed. 2005, 44, 7059−7062. (d) Bis, J. A.; Vishweshwar, P.; Middleton, R. A.; Zaworotko, M. J. Cryst. Growth Des. 2006, 6, 1048−1053. (e) Yan, D.; Delori, A.; Lloyd, G. O.; Frišcǐ ć, T.; Day, G. M.; Jones, W.; Lu, J.; Wei, M.; Evans, D. G.; Duan, X. Angew. Chem., Int. Ed. 2011, 50, 12483− 12486. (11) (a) Ma, B.-Q.; Coppens, P. Chem. Commun. 2003, 412−413. (b) Bhogala, B. R.; Nangia, A. Cryst. Growth Des. 2003, 3, 547−554. (c) Bhogala, B. R.; Basavoju, S.; Nangia, A. Cryst. Growth Des. 2005, 5, 1683−1686. (d) Zeng, Q.; Wu, D.; Wang, C.; Ma, H.; Lu, J.; Liu, C.; Xu, S.; Li, Y.; Bai, C. Cryst. Growth Des. 2005, 5, 1889−1896. (e) Hisamatsu, S.; Masu, H.; Azumaya, I.; Takahashi, M.; Kishikawa, K.; Kohmoto, S. Cryst. Growth Des. 2011, 11, 1453−1457. (12) (a) Aitipamula, S.; Desiraju, G. R.; Jaskólski, M.; Nangia, A.; Thaimattam, R. CrystEngComm 2003, 5, 447−450. (b) Vangala, V. R.; Mondal, R.; Broder, C. K.; Howard, J. A. K.; Desiraju, G. R. Cryst. Growth Des. 2005, 5, 99−104. (c) Aitipamula, S.; Nangia, A. Chem. Commun. 2005, 3159−3161. (d) Sarma, R. J.; Baruah, J. B. CrystEngComm 2005, 7, 706−710. (13) Crystal 1c has been reported previously in ref 8b. (14) Sheldrick, G. M. A short history of SHELX. Acta Crystallogr. 2008, A64, 112−122. (15) Spek, A. L. J. Appl. Crystallogr. 2003, 36, 7−13.

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Hydrogen-Bonded 1D Chains Formed from Adamantane-Based

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