J = 8.1 Hz), 5.07 (t, J = 27.6 Hz), 2.36 (s). 13C NMR (101
MHz, MeOD) d 162.22, 156.88, 148.48, 142.63, 129.82, 127.89,
126.83, 125.79, 125.57, 125.20, 125.00, 118.28, 118.07, 51.83,
helpful discussions, Sabine Stempfhuber and Dr Manfred Zabel
for the X-ray single crystal analysis.
11.28. ESI-MS(+) (in CH3CN): m/z 100% [12Zn24++ClO4 ]3+
-
Notes and references
- 440.3, 20% [1Zn2+–H+]+ - 608.3, 10% [12Zn24++2ClO4 ]2+
-
1 P. J. Stang, J. Org. Chem., 2009, 74, 2–20.
710.3.
2 M. D. Ward, Chem. Commun., 2009, 4487–4499.
3 S. L. James, Chem. Soc. Rev., 2009, 38, 1744–1758.
4 E. Zangrando, M. Casanova and E. Alessio, Chem. Rev., 2008, 108,
4979–5013.
X-ray structure determination
5 B. Linton and A. D. Hamilton, Chem. Rev., 1997, 97, 1669–1680.
6 P. Mal, B. Breiner, K. Rissanen and J. R. Nitschke, Science, 2009, 324,
1697–1699.
7 R. Warmuth, Angew. Chem., Int. Ed. Engl., 1997, 36, 1347–1350.
8 R. Warmuth and M. A. Marvel, Angew. Chem., Int. Ed., 2000, 39,
1117–1119.
9 M. Yoshizawa, J. K. Klosterman and M. Fujita, Angew. Chem., Int.
Ed., 2009, 48, 3418–3438.
10 B. Olenyuk, J. A. Whiteford, A. Fechtenkotter and P. J. Stang, Nature,
1999, 398, 796–799.
11 M. D. Levin and P. J. Stang, J. Am. Chem. Soc., 2000, 122, 7428–7429.
12 D. T. de Lill, D. J. Bozzuto and C. L. Cahill, Dalton Trans., 2005,
2111–2115.
13 Q. R. Fang, G. S. Zhu, M. Xue, Z. P. Wang, J. Y. Sun and S. L. Qiu,
Cryst. Growth Des., 2008, 8, 319–329.
14 L. Q. Ma and W. B. Lin, J. Am. Chem. Soc., 2008, 130,
13834–13835.
15 X. Y. Zhao, D. D. Liang, S. X. Liu, C. Y. Sun, R. G. Cao, C. Y. Gao, Y.
H. Ren and Z. M. Su, Inorg. Chem., 2008, 47, 7133–7138.
16 D. K. Bocar, G. S. Papaefstathiou, T. D. Hamilton, Q. L. Chu, I. G.
Georgiev and L. R. MaeGillivray, Eur. J. Inorg. Chem., 2007, 4559–
4568.
Crystal data for C71H80N14O27Zn2Cl4, CCDC 771310 M = 1844.15
-1
¯
˚
˚
g mol , triclinic, P1, a = 14.7024(4) A, b = 15.6663(3) A, c ◦=
◦
◦
˚
19.1867(5) A, a = 87.631(2) , b = 77.559(2) , g = 89.732(2) ,
3
˚
V = 4311.81(19) A , Z = 2, 21330 reflections measured, 14378
independent (Rint = 0.0239), which were used in all calculations.
The final wR2 was 0.1729 (all data). Intensity data were collected
˚
with a graphite-monochromated Mo-Ka radiation (l = 1.54184 A)
at 123 K on a Goniometer Xcalibur, detector: Ruby (Gemini
ultra Mo). Data collection, structure solution and refinement
used programs: SHELXL,46 PLATON47 and SQUEEZE. R1 is
calculated for observed data and wR2 for all data.
Crystal data for 2 (C32H31N7O2·CH4O), CCDC 789485 M =
-1
˚
1123.32 g mol , orthorhombic, Fdd2, a = 24.4639(7) A, b =
3
˚
˚
˚
26.8690(8) A, c = 17.3167(4) A, V = 11382.6(5) A , Z = 8, 15515
reflections measured, 4860 independent (Rint = 0.0327), which
were used in all calculations. The final wR2 was 0.1151 (all data).
Intensity data were collected with a graphite-monochromated Mo-
17 Q. Shi, Y. T. Sun, L. Z. Sheng, K. F. Ma, M. L. Hu, X. G. Hu and S.
M. Huang, Cryst. Growth Des., 2008, 8, 3401–3407.
18 R. Vilar, Eur. J. Inorg. Chem., 2008, 357–367.
19 M. Yoshizawa, J. Nakagawa, K. Kurnazawa, M. Nagao, M. Kawano,
T. Ozeki and M. Fujita, Angew. Chem., Int. Ed., 2005, 44, 1810–1813.
20 M. Yoshizawa, M. Nagao, K. Kumazawa and M. Fujita, J. Organomet.
Chem., 2005, 690, 5383–5388.
21 M. A. Galindo, S. Galli, J. A. R. Navarro and M. A. Romero, Dalton
Trans., 2004, 2780–2785.
22 J. Y. Zhang, P. W. Miller, M. Nieuwenhuyzen and S. L. James, Chem.–
Eur. J., 2006, 12, 2448–2453.
˚
Ka radiation (l = 1.54184 A) at 123 K on a Goniometer Xcalibur,
detector: Ruby (Gemini ultra Mo).
DFT calculations
Molecular modeling calculations were performed using the DFT
program “PRIRODA”. A PBE functional which includes electron
density gradient was used. TZ2p-atomic basis sets of grouped
Gaussian functions were used to solve the Kohn–Sham equations.
The criterion for convergence was a difference below 0.01 kcal
23 Z. Grote, R. Scopelliti and K. Severin, Eur. J. Inorg. Chem., 2007,
694–700.
mol-1
-1 in the energy between two sequential structures. Various
˚
A
24 K. Uehara, K. Kasai and N. Mizuno, Inorg. Chem., 2010, 49, 2008–
2015.
stationary points on potential energy surface (PES) were deter-
mined from analytical calculations of second energy derivatives
(Hessian matrixes).
25 E. Hollo-Sitkei, G. Tarkanyi, L. Parkanyi, T. Megyes and G. Besenyei,
Eur. J. Inorg. Chem., 2008, 1573–1583.
26 S. Derossl, M. Casanova, E. Iengo, E. Zangrando, M. Stener and E.
Alessio, Inorg. Chem., 2007, 46, 11243–11253.
27 P. S. Mukherjee, K. S. Min, A. M. Arif and P. J. Stang, Inorg. Chem.,
2004, 43, 6345–6350.
28 X. F. Huang, K. Nakanishi and N. Berova, Chirality, 2000, 12, 237–255.
29 P. Ballester, A. I. Oliva, A. Costa, P. M. Deya, A. Frontera, R. M.
Gomila and C. A. Hunter, J. Am. Chem. Soc., 2006, 128, 5560–
5569.
30 A. W. Kleij, M. Kuil, D. M. Tooke, M. Lutz, A. L. Spek and J. N. H.
Reek, Chem.–Eur. J., 2005, 11, 4743–4750.
31 A. D. Cort, L. Mandolini, C. Pasquini, K. Rissanen, L. Russo and L.
Schiaffino, New J. Chem., 2007, 31, 1633–1638.
32 B. Ko¨nig and J. Svoboda, in Macrocyclic Chemistry: Current Trends
and Future Perspectives, ed. G. Karsten, pp. 87–103.
33 V. Amendola, L. Fabbrizzi, P. Pallavicini, L. Parodi and A. Perotti, J.
Chem. Soc., Dalton Trans., 1998, 2053–2057.
34 V. Amendola, C. Brusoni, L. Fabbrizzi, C. Mangano, H. Miller, P.
Pallavicini, A. Perotti and A. Taglietti, J. Chem. Soc., Dalton Trans.,
2001, 3528–3533.
NMR measurements
NMR spectra were recorded at 300 K on a Bruker Avance
DRX 600 (600.13 MHz) and on a Bruker Avance III 600
(600.25 MHz), equipped with a broadband triple-resonance probe
and a TCI cryoprobe, respectively. The maximum Z-gradient
field strength of both probes was 53.5 G cm-1. For the NMR
diffusion measurements (PFGSE), a stimulated echo sequence
using bipolar gradients was applied. NMR data were processed
and evaluated with Bruker’s TOPSPIN 2.1. and the included
t1/t2 software package was used for the calculation of diffusion
coefficients.
35 K. Navakhun, P. A. Gale, S. Camiolo, M. E. Light and M. B.
Hursthouse, Chem. Commun., 2002, 2084–2085.
36 G. W. Bates, P. A. Gale, M. E. Light, M. I. Ogden and C. N. Warriner,
Dalton Trans., 2008, 4106–4112.
37 C. J. Nyman, E. W. Murbach and G. B. Millard, J. Am. Chem. Soc.,
1955, 77, 4194–4197.
Acknowledgements
This work was supported by the Humboldt Foundation. We
gratefully acknowledge Prof. Burkhard Ko¨nig for support and
This journal is
The Royal Society of Chemistry 2011
Dalton Trans., 2011, 40, 2778–2786 | 2785
©