Paper
NJC
Table 2 Crystallographic data and structure refinement details for 1–3
1
2
3
Empirical formula
fw
l (Å)
Temperature (K)
Cryst. syst.
Space group
a (Å)
b (Å)
c (Å)
C
14
H
12Cl18MnN
9
OS
C
16
H
18Cl18FeN
9
O
2
S
2
C
16 9 2 2
H18Cl18CoN O S
1047.43
0.71073
100(2)
Triclinic
P1
14.257(2)
16.101(2)
19.044(3)
104.391(2)
102.766(2)
111.467(2)
3697.2(9)
4
1126.48
0.71073
296(2)
Triclinic
P1%
10.0591(4)
13.5688(5)
16.6349(6)
79.4670(10)
76.0640(10)
75.1320(10)
2112.09(14)
2
1129.54
0.71073
296(2)
Triclinic
P1%
10.171(3)
13.499(4)
16.468(5)
79.309(6)
76.007(6)
74.967(6)
2100.6(10)
2
a (1)
b (1)
g (1)
V (Å )
3
Z
Density
1.882
1.002
0.0722
0.1074
1.771
1.005
0.0749
0.1718
1.786
1.004
0.0770
0.1981
GOOF
a
R
1
(I Z 2s)
(I Z 2s)
b
wR
2
a
b
2
o
2 2
2 2 1/2
R
1
= SJF
o
| ꢂ |F
c
J/S|F
o
|. wR
2
= [S[w(F
ꢂ F
c
) ]/S[w(F
o
) ]]
.
Acknowledgements
3 (a) N. Q. Shixaliyev, A. M. Maharramov, A. V. Gurbanov,
V. G. Nenajdenko, V. M. Muzalevskiy, K. T. Mahmudov and
M. N. Kopylovich, Catal. Today, 2013, 217, 76; (b) N. Q.
Shixaliyev, A. M. Maharramov, A. V. Gurbanov, N. V.
Gurbanova, V. G. Nenajdenko, V. M. Muzalevskiy, K. T.
Mahmudov and M. N. Kopylovich, J. Mol. Struct., 2013,
This work has been partially supported by the Foundation for
Science and Technology (FCT), Portugal [PEst-OE/QUI/UI0100/
2013 and ‘‘Investigador 2013’’ programs], as well as by the Baku
State University, Azerbaijan. K.T.M. and M.N.K. express grati-
tude to FCT for the post-doc fellowship and working contract.
The authors acknowledge the Portuguese NMR Network of
mass-spectrometry (Dr Conceiç ˜a o Oliveira) for the ESI-MS
measurements.
1041, 213.
4
(a) P. Metrangolo, H. Neukirch, T. Pilati and G. Resnati, Acc.
Chem. Res., 2005, 38, 386; (b) P. Metrangolo and G. Resnati,
Halogen Bonding: Fundamentals and Applications, Springer,
Berlin, Germany, 2008; (c) A. Priimagi, G. Cavallo, P. Metrangolo
and G. Resnati, Acc. Chem. Res., 2013, 46, 2686; (d) G. Cavallo,
P. Metrangolo, T. Pilati, G. Resnati, M. Sansotera and G. Terraneo,
Chem. Soc. Rev., 2010, 39, 3772; (e) E. Parisini, P. Metrangolo,
T. Pilati, G. Resnati and G. Terraneo, Chem. Soc. Rev., 2011,
40, 2267.
References
1
Hydrogen bonding in organic synthesis, ed. P. M. Pihko,
Wiley-VCH, Weinheim, 2009.
2
(a) G. Gilli and P. Gilli, The Nature of the Hydrogen Bond:
Outline of a Comprehensive Hydrogen Bond Theory, Oxford
University Press, Oxford, 2009; (b) G. Gilli, F. Bellucci,
V. Ferretti and V. Bertolasi, J. Am. Chem. Soc., 1989,
5 M. N. Kopylovich and A. J. L. Pombeiro, Coord. Chem. Rev.,
2011, 255, 339.
6 (a) J. A. Flores, Y. Kobayashi and H. V. R. Dias, Dalton Trans.,
2011, 40, 10351; (b) H. V. R. Dias, J. A. Flores, M. Pellei,
B. Morresi, G. G. Lobbia, S. Singh, Y. Kobayashi,
M. Yousufuddin and C. Santini, Dalton Trans., 2011,
40, 8569; (c) J. A. Flores and H. V. R. Dias, Inorg. Chem.,
2008, 47, 4448; (d) H. V. R. Dias and S. Singh, Dalton Trans.,
2006, 1995; (e) H. V. R. Dias, S. Singh and T. R. Cundari,
Angew. Chem., Int. Ed., 2005, 44, 4907; ( f ) H. V. R. Dias and
S. Singh, Inorg. Chem., 2004, 43, 7396; (g) H. V. R. Dias and
S. Singh, Inorg. Chem., 2004, 43, 5786; (h) K. Suematsu,
Chem. Pharm. Bull., 1984, 32, 291.
7 (a) G. Tojo and M. Fernandez, Oxidation of Alcohols to
Aldehydes and Ketones, Springer, Berlin, Germany, 2006,
pp. 1–97; (b) M. Hudlicky, Oxidations in Organic Chemistry,
ACS, Washington, DC, 1990, pp. 60–64; (c) J. E. Backwall,
Modern Oxidation Methods, Wiley-VCH, New York, 2004,
pp. 83–118; (d) A. M. Kirillov and G. B. Shul’pin, Coord.
Chem. Rev., 2013, 257, 732; (e) Y. Y. Karabach,
1
11, 1023; (c) M. N. Kopylovich, K. T. Mahmudov, A. Mizar
and A. J. L. Pombeiro, Chem. Commun., 2011, 47, 7248;
d) M. N. Kopylovich, T. C. O. Mac Leod, M. Haukka,
(
G. I. Amanullayeva, K. T. Mahmudov and A. J. L.
Pombeiro, J. Inorg. Biochem., 2012, 115, 72; (e) M. N.
Kopylovich, M. J. Gajewska, K. T. Mahmudov, M. F. C.
Guedes da Silva, M. V. Kirillova, P. J. Figiel, J. Sanchiz and
A. J. L. Pombeiro, New J. Chem., 2012, 36, 1646; ( f ) K. T.
Mahmudov, M. N. Kopylovich and A. J. L. Pombeiro, Coord.
Chem. Rev., 2013, 257, 1244; (g) K. T. Mahmudov,
M. N. Kopylovich, A. M. Maharramov, M. M. Kurbanova,
A. V. Gurbanov and A. J. L. Pombeiro, Coord. Chem. Rev.,
2014, 265, 1; (h) M. N. Kopylovich, K. T. Mahmudov,
M. F. C. Guedes da Silva, A. M. Kirillov and A. J. L.
Pombeiro, Dalton Trans., 2011, 40, 12472; (i) M. N. Kopylovich,
K. T. Mahmudov, M. Haukka, K. V. Luzyanin and
A. J. L. Pombeiro, Inorg. Chim. Acta, 2011, 374, 175.
4
814 | New J. Chem., 2014, 38, 4807--4815
This journal is ©The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2014