Paper
Dalton Transactions
filtration, the volume of the filtrate was reduced and ethyl
ether was added. After 2 h, a needle-shaped light brown-
coloured crystalline product 1 suitable for X-ray analysis was
isolated. Yield: 70%. Mp 240–242 °C. IR (KBr pellet) 2968,
2927, 2877, 1745, 1701, 1655, 1638, 1601, 1561, 1491, 1459,
1400, 1378, 1342, 1320, 1295, 1249, 1222, 1102, 1030, 961, 897,
829, 792, 750 cm−1. Anal. Calcd for [C33H37CuI3NO3S2]: C,
39.48; H, 3.71; N, 1.40; S, 6.39. Found: C, 39.74; H, 3.55; N,
1.64; S, 6.41. MS (ESI) m/z: 548.36 [Cu(L1)]+.
1990, 29, 4723; (d) M. J. MacLachlan, M. K. Park and
L. K. Thompson, Inorg. Chem., 1996, 35, 5492;
(e) S. Brooker, Coord. Chem. Rev., 2001, 222, 33; (f) D. J. de
Geest, A. Noble, B. Moubaraki, K. S. Murray, D. S. Larsen
and S. Brooker, Dalton Trans., 2007, 467; (g) S. A. Cameron
and S. Brooker, Inorg. Chem., 2011, 50, 3697.
2 (a) H.-S. Kim, I.-C. Kwon and J.-H. Choi, J. Heterocycl.
Chem., 1999, 36, 1285; (b) Y. Habata, J. Seo, S. Otawa,
F. Osaka, K. Noto and S. S. Lee, Dalton Trans., 2006, 2202.
3 (a) D. Jung, R. Chamura, Y. Habata and S. S. Lee, Inorg.
Chem., 2011, 50, 8392; (b) S.-G. Lee, K.-M. Park, Y. Habata
and S. S. Lee, Inorg. Chem., 2013, 52, 8416; (c) S. Kim,
L. F. Lindoy and S. S. Lee, Coord. Chem. Rev., 2014, 280,
176–202.
Preparation of 2a, [(Cu2I2)2(L2)2]·2toluene·2CH3CN. Toluene
(2.6 mL) was added to a dichloromethane (0.2 mL) solution of
L2 (2.0 mg, 0.004 mmol); then CuI (0.4 mg, 0.002 mmol) in
acetonitrile (0.2 mL) was layered on the toluene phase; the
(layered) mixture afforded a block-shaped colourless crystalline
product 2a suitable for X-ray analysis. Mp 223–225 °C. IR (KBr,
pellet): 3022, 2925, 1719, 1702, 1674, 1654, 1638, 1627, 1544,
1509, 1492, 1449, 1336, 1245, 1106, 1560, 1106, 1060, 992, 851,
751 cm−1. Anal. Calcd for [C67H65Cu2I2N3O4S4]: C, 54.17; H,
4.41; N, 2.83; S, 8.63. Found: C, 54.39; H, 4.36; N, 2.51; S, 8.77.
MS (ESI) m/z: 1033.25 [Cu(L2)]+.
4 Y. Habata, J. Seo, S. Otawa, F. Osaka, K. Noto and S. S. Lee,
Dalton Trans., 2006, 2202.
5 (a) Y. Jin, I. Yoon, J. Seo, J.-E. Lee, S.-T. Moon, J. Kim,
S. W. Han, K.-M. Park, L. F. Lindoy and S. S. Lee, Dalton
Trans., 2005, 788; (b) J.-E. Lee, Y. Jin, J. Seo, I. Yoon,
M. R. Song, S. Y. Lee, K.-M. Park and S. S. Lee, Bull. Korean
Chem. Soc., 2006, 27, 203; (c) J. Seo, S. Park, S. S. Lee,
M. Fainerman-Melnikova and L. F. Lindoy, Inorg. Chem.,
2009, 48, 2770.
X-ray crystallographic analysis
Crystal data for 1, 2a and 2b were collected using a Bruker
SMART APEX II ULTRA diffractometer equipped with graphite
monochromated Mo Kα radiation (λ = 0.71073 Å) generated by
a rotating anode. The cell parameters for the compounds were
obtained from a least-squares refinement of the spot (from 36
collected frames). Data collection, data reduction, and semi-
empirical absorption correction were carried out using the
software package of APEX2.12 All of the calculations for the
structure determination were carried out using the SHELXTL
package.13 In all cases, all non-hydrogen atoms except in the
toluene and acetonitrile molecules were refined anisotropically
and all hydrogen atoms were placed in idealized positions and
refined isotropically in a riding manner along with their
respective parent atoms. 2a and 2b show high R1 values
because of the solvent loss and the structural rearrangement.
Since the lattice solvent molecules in 2a and 2b are highly dis-
ordered, the contribution of solvent electron density was
removed by the SQUEEZE routine in PLATON.14 The relevant
crystal data collection and refinement data for the crystal struc-
tures of 1, 2a and 2b are summarised in Table S1.†
6 (a) J. Y. Lee, J. Kwon, C. S. Park, J.-E. Lee, W. Sim, J. S. Kim,
J. Seo, I. Yoon, J. H. Jung and S. S. Lee, Org. Lett., 2007, 9,
493; (b) J. Y. Lee, H. J. Kim, J. H. Jung, W. Sim and S. S. Lee,
J. Am. Chem. Soc., 2008, 130, 13838; (c) J. Y. Lee, H. J. Kim,
C. S. Park, W. Sim and S. S. Lee, Chem. – Eur. J., 2009, 15,
8989.
7 (a) R. J. A. Janssen, L. F. Lindoy, O. A. Matthews,
A. N. Sobolev and A. H. J. White, J. Chem. Soc., Chem.
Commun., 1995, 735; (b) A. H. M. Elwahy and A. A. Abbas,
Tetrahedron, 2000, 56, 885; (c) K. F. Sultana, S. Y. Lee,
J.-E. Lee, J. Seo and S. S. Lee, Inorg. Chem. Commun., 2007,
10, 1496.
8 A. W. Addison, T. N. Rao, J. Reedijk, J. van Rijn and
G. C. Verschoor, J. Chem. Soc., Dalton Trans., 1984, 1349.
9 (a) H. J. Kim, Y. Jin, J. Seo, J.-E. Lee, J. Y. Lee and S. S. Lee,
Inorg. Chem. Commun., 2006, 9, 1040; (b) K.-M. Park,
I. Yoon, J. Seo, J.-E. Lee, J. Kim, K. S. Choi, O.-S. Jung and
S. S. Lee, Cryst. Growth Des., 2005, 5, 1707; (c) M. Heller and
W. S. Sheldrick, Z. Anorg. Allg. Chem., 2003, 629, 1589;
(d) N. R. Brooks, A. J. Brake, N. R. Champness, P. A. Cooke,
P. Hubberstey, D. M. Proserpio, C. Wilson and M. Schröder,
J. Chem. Soc., Dalton Trans., 2001, 456; (e) D. P. Danks,
N. R. Champness and M. Schröder, Coord. Chem. Rev.,
1998, 174, 417; (f) M. Munakata, L. P. Wu, T. Kuroda-Sowa,
M. Maekawa, Y. Suenaga and S. Nakagawa, J. Chem. Soc.,
Dalton Trans., 1996, 1525; (g) L. Chen, L. K. Thompson and
J. N. Bridson, Can. J. Chem., 1992, 70, 2709.
Acknowledgements
This work was supported by NRF (2012R1A4A1027750 and
2013R1A2A2A01067771).
10 E. C. Constable, G. Zhang, C. E. Housecroft, M. Neuburger
and J. A. Zampese, CrystEngComm, 2010, 12, 1764.
Notes and references
1 (a) N. H. Pilkington and R. Robson, Aust. J. Chem., 1970, 11 (a) E.-J. Kang, S. Y. Lee, H. Lee and S. S. Lee, Inorg. Chem.,
23, 2225; (b) A. H. Alberts, J.-M. Lehn and D. Parker,
J. Chem. Soc., Dalton Trans., 1985, 2311; (c) R. Menif,
A. E. Martell, P. J. Squattrito and A. Clearfield, Inorg. Chem.,
2010, 49, 7510; (b) Y. Jin, H. J. Kim, J. Y. Lee, S. Y. Lee,
W. J. Shim, S. H. Hong and S. S. Lee, Inorg. Chem., 2010,
49, 10241; (c) I.-H. Park and S. S. Lee, CrystEngComm, 2011,
4532 | Dalton Trans., 2016, 45, 4528–4533
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