Citation: LI Wei-Dong, FANG Xu, QIAO Rui, CHEN Shui-Sheng. Non-covalent Bonded 3D Supramolecular Architectures Based on Acid-base Adducts[J]. Chinese Journal of Structural Chemistry, ;2016, 35(1): 46-54. doi: 10.14102/j.cnki.0254-5861.2011-0805 shu

Non-covalent Bonded 3D Supramolecular Architectures Based on Acid-base Adducts

1.
College of Chemistry & Chemical Engineering, Fuyang Normal College, Fuyang 236041, China

Received Date: 1 May 2015
Available Online: 24 September 2015
Fund Project:

Two novel acid-base adducts, [H₂L₁²⁺](Hpbda)₂ (1, L₁ = 1,4-di(1H-imidazol-4-yl) benzene, H₂pbda = 1,4-benzenedicarboxylic acid) and [H₂L₂²⁺](NO₃)₂ (2, L₂ = 1,4-di(1-carboxy- methyl-imidazol-4-yl)benzene), have been prepared and characterized by single-crystal X-ray diffraction, IR spectroscopy and elemental analysis. Compound 1 crystallizes in monoclinic, space group P2₁/n with a = 5.3525(11), b = 9.1471(19), c = 19.314(4) Å, β = 92.342(3)°, V = 944.8(3) Å³, Z = 2, C₁₆H₁₆N₆O₁₀, M_r = 452.35, D_c = 1.590 g/cm³, μ = 0.135 mm^-1, S = 1.058, F(000) = 468, the final R = 0.0661 and wR = 0.1887 for 2298 observed reflections (I > 2σ(I)). Compound 2 crystallizes in monoclinic, space group P2₁/c with a = 9.6923(10), b = 17.2950(17), c = 7.1880(7) Å, β = 94.801(2)°, V = 1200.7(2) Å³, Z = 2, C₂₈H₂₂N₄O₈, M_r = 542.50, D_c = 1.501 g/cm³, μ = 0.112 mm^-1, S = 1.060, F(000) = 564, the final R = 0.0394 and wR = 0.1017 for 2768 observed reflections (I > 2σ(I)). In the title compounds, both of L₁ and L₂ ligands act as weak base to accept protons to exhibit diprotonated H₂L₁²⁺ and H₂L₂²⁺ form, which can effectively employ as hydrogen bonding donors to combine anion moieties to form binary adducts respectively. In the crystal packing diagram of two polymers, there exist extensive noncovalent interactions including charge-transfer interactions, C(N)-H…π and N-H…O, C-H…O, O-H…O hydrogen bonding interactions between co-crystal moieties which consolidate the structures of supramolecular polymers, thus generating three-dimensional (3D) frameworks.
- synthesis,
- acid-base adducts,
- crystal structure,
- noncovalent interactions
1. [1]
  (1) Han, L. L.; Li, Z. H.; Chen, J. S.; Wang, X. P.; Sun, D. Solution and mechanochemical syntheses of two novel cocrystals: ligand length modulated
2. [2]
  (1) 1)interpenetration of hydrogen-bonded 2D 6³- hcb networks based on a robust trimeric heterosynthon. Cryst. Growth Des. 2014, 14, 1221-1226.
3. [3]
  (2) Wang, L.; Wen, X.; Li, P.; Wang, J.; Yang, P.; Zhang, H.; Deng, Z. 2:1 5-Fluorocytosine-acesulfame CAB cocrystal and 1:1 5-fluorocytosine-acesulfame salt hydrate with enhanced stability against hydration. CrystEngComm. 2014, 16, 8537-8545.
4. [4]
  (3) Wu, X.; Wang, M.; Du, M.; Lu, J.; Chen, J.; Khan, A.; Usman, R.; Wei, X.; Feng, Q.; Xu, C. Reversible accommodation and desorption of aromatics on a charge transfer cocrystal involving an anthracene derivative and TCNQ. Cryst. Growth Des. 2015, 15, 434-441.
5. [5]
  (4) Chen, J. M.; Li, S.; Lu, T. B. Pharmaceutical cocrystals of ribavirin with reduced release rates. Cryst. Growth Des. 2014, 14, 6399-6408.
6. [6]
  (5) Chen, S. S.; Wang, P.; Takamizawa, S.; Okamura, T. A.; Chen, M.; Sun, W. Y. Zinc(II) and cadmium(II) metal-organic frameworks with 4-imidazole containing tripodal ligand: sorption and anion exchange properties. Dalton Trans. 2014, 43, 6012-6020.
7. [7]
  (6) Song, W. C.; Pan, Q.; Song, P. C.; Zhao, Q.; Zeng, Y. F.; Hu, T. L.; Bu, X. H. Two unprecedented 10-connected bct topological metal-organic frameworks constructed from cadmium clusters. Chem. Commun. 2010, 46, 4890-4892.
8. [8]
  (7) Chen, S. S.; Zhang, S. P.; Li, H. Q.; Shao, S. C. Synthesis, structure and spectral properties of a novel triaryl substituted triazole and its Co(II) complex. Chin. J. Struct. Chem. 2010, 29, 341-346.
9. [9]
  (8) Chen, S. S.; Chen, M.; Takamizawa, S.; Wang, P.; Lv, G. C.; Sun, W. Y. Porous cobalt(II)-imidazolate supramolecular isomeric frameworks with selective gas sorption property. Chem. Commun. 2011, 47, 4902-4904.
10. [10]
  (9) Chen, Q. Y.; Zheng, F. K.; Li, Y.; Zou, W. Q.; Chen, H. F.; Ding, T. Y.; Guo, G. C.; Wu, A. Q. Crystal structures and photoluminescence of two new tetrazole-based complexes. Chin. J. Struct. Chem. 2009, 28, 195-199.
11. [11]
  (10) Ouellette, W.; Jones, S.; Zubieta, J. Solid state coordination chemistry of metal-1,2,4-triazolates and the related metal-4-pyridyltetrazolates. CrystEngComm. 2011, 13, 4457-4485.
12. [12]
  (11) Chen, S. S.; Lv, G. C.; Okamura, T. A.; Chen, M.; Sun, W. Y. Entangled coordination frameworks with 1,4-di(1H-imidazol-4-yl)benzene. Cryst. Growth Des. 2011, 11, 1082-1090.
13. [13]
  (12) Chen, S. S.; Chen, M.; Takamizawa, S.; Chen, M. S.; Su, Z.; Sun, W. Y. Temperature dependent selective gas sorption of the microporous metal-imidazolate framework [Cu(L)] (H₂L = 1,4-di(1H-imidazol-4-yl)benzene). Chem. Commun. 2011, 47, 752-754.
14. [14]
  (13) Jin, S.; Yan, P.; Wang, D.; Xu, Y.; Jiang, Y.; Hu, L. Salt and co-crystal formation from 6-bromobenzo[d]thiazol-2-amine and different carboxylic acid derivatives. J. Mol. Struct. 2012, 1016, 55-63.
15. [15]
  (14) Wei, L. H.; Wang, Z. L.; Li, M. X. Crystal structure, hirshfeld surface analysis and quantum mechanical study of a cocrystal based on 1,3-di(4-pyridyl)propane and 3-((4'-carboxybenzyl)oxy)benzoic acid. Chin. J. Struct. Chem. 2013, 32, 1367-1373.
16. [16]
  (15) Zeng, Q.; Wu, D.; Ma, H.; Shu, C.; Wang, C. Polymeric hydrogen-bonded supramolecules by self-assembling of adamantane derivatives with bipyridines. CrystEngComm. 2006, 8, 189-201.
17. [17]
  (16) Pan, Y.; Li, K.; Bi, W.; Li, J. Cocrystallization of adamantane-1,3-dicarboxylic acid and 4,4'-bipyridine. Acta Crystallogr., Sect. C 2008, 64, o41.
18. [18]
  (17) Bolton, O.; Simke, L. R.; Pagoria, P. F.; Matzger, A. J. High power explosive with good sensitivity: a 2:1 cocrystal of CL-20:HMX. Cryst. Growth Des. 2012, 12, 4311-4314.
19. [19]
  (18) Sarfraz, A.; Simo, A.; Fenger, R.; Christen, W.; Rademann, K.; Panne, U.; Emmerling, F. Morphological diversity of caffeine on surfaces: needles and hexagons. Cryst. Growth Des. 2012, 12, 583-588.
20. [20]
  (19) Chen, S. S.; Fan, J.; Okamura, T. A.; Chen, M. S.; Su, Z.; Sun, W. Y.; Ueyama, N. Synthesis, crystal structure, and photoluminescence of a series of zinc(II) coordination polymers with 1,4-di(1H-imidazol-4-yl)benzene and varied carboxylate ligands. Cryst. Growth Des. 2009, 10, 812-822.
21. [21]
  (20) Sheldrick, G. M. SHELXS-97, Programm for the Solution of Crystal Structure. University of Göttingen 1997.
22. [22]
  (21) Sheldrick, G. M. SHELXL-97, Programm for the Refinement of Crystal Structure. University of Göttingen 1997.
23. [23]
  (22) Roy, S.; Biradha, K. Exploration of salts and cocrystals of 2,2',6,6'-tetracarboxybiphenyl with acetic acid, monobasic and dibasic N-heterocycles, and N^- oxides. Cryst. Growth Des. 2013, 13, 1342-1349.
24. [24]
  (23) Chen, S. S.; Qiao, R.; Sheng, L. Q.; Yang, S. A new three-dimensional supramolecular polymer built from non-covalent bonding interactions. Chin. J. Struct. Chem. 2014, 33, 557-562.
25. [25]
  (24) Duan, J.; Guo, P.; Pan, Q. Q.; Wu, Y.; Wu, X. Q.; Li, H. Crystal structure and characterization of salicylic acid-benzene azimide cocrystal. Chin. J. Struct. Chem. 2013, 32, 289-295.
26. [26]
  (25) Li, X. F.; Cao, R. A series of mononuclear complexes constructed from transition metals and amino acid derived ligands: syntheses, structures and photoluminescence. Chin. J. Struct. Chem. 2009, 28, 1439-1447.
27. [27]
  (26) Chen, S. S.; Liu, Q.; Zhao, Y.; Qiao, R.; Sheng, L. Q.; Liu, Z. D.; Yang, S.; Song, C. F. New metal-organic frameworks constructed from the 4-imidazole-carboxylate ligand: structural diversities, luminescence, and gas adsorption properties. Cryst. Growth Des. 2014, 14, 3727-3741.
28. [28]
  (27) Wu, G.; Wang, X. F.; Okamura, T. A.; Sun, W. Y.; Ueyama, N. Syntheses, structures, and photoluminescence properties of metal(II) halide complexes with pyridine-containing flexible tripodal ligands. Inorg. Chem. 2006, 45, 8523-8532.
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