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Volume 68 
Part 12 
Pages m1480-m1481  
December 2012  

Received 16 August 2012
Accepted 8 November 2012
Online 14 November 2012

Key indicators
Single-crystal X-ray study
T = 120 K
Mean [sigma](C-C) = 0.005 Å
R = 0.053
wR = 0.147
Data-to-parameter ratio = 18.0
Details
Open access

Bis{(E)-3-[2-(hydroxyimino)propanamido]-2,2-dimethylpropan-1-aminium} bis[[mu]-(E)-N-(3-amino-2,2-dimethylpropyl)-2-(hydroxyimino)propanamido(2-)]bis{[(E)-N-(3-amino-2,2-dimethylpropyl)-2-(hydroxyimino)propanamide]copper(II)} bis((E)-{3-[2-(hydroxyimino)propanamido]-2,2-dimethylpropyl}carbamate) acetonitrile disolvate

aDepartment of Chemistry, Kiev National Taras Shevchenko University, Volodymyrska str. 62, Kiev 01601, Ukraine, and bUniversity of Joensuu, Department of Chemistry, PO Box 111, FI-80101 Joensuu, Finland
Correspondence e-mail: annpavlis@ukr.net

The reaction between copper(II) nitrate and (E)-N-(3-amino-2,2-dimethylpropyl)-2-(hydroxyimino)propanamide led to the formation of the dinuclear centrosymmetric copper(II) title complex, (C8H18N3O2)2[Cu2(C8H15N3O2)2(C8H17N3O2)2](C9H16N3O4)2·2CH3CN, in which an inversion center is located at the midpoint of the Cu2 unit in the center of the neutral [Cu2(C8H15N3O2)2(C8H17N3O2)2] complex fragment. The Cu2+ ions are connected by two N-O bridging groups [Cu...Cu separation = 4.0608 (5) Å] while the CuII ions are five-coordinated in a square-pyramidal N4O coordination environment. The complex molecule co-crystallizes with two molecules of acetonitrile, two molecules of the protonated ligand (E)-3-[2-(hydroxyimino)propanamido]-2,2-dimethylpropan-1-aminium and two negatively charged (E)-{3-[2-(hydroxyimino)propanamido]-2,2-dimethylpropyl}carbamate anions, which were probably formed as a result of condensation between (E)-N-(3-amino-2,2-dimethylpropyl)-2-(hydroxyimino)propanamide and hydrogencarbonate anions. In the crystal, the complex fragment [Cu2(C8H15N3O2)2(C8H17N3O2)2] and the ion pair C8H18N3O2+.C9H16N3O4- are connected via an extended system of hydrogen bonds.

Related literature

For properties of polynuclear complexes, see: Krämer & Fritsky (2000[Krämer, R. & Fritsky, I. O. (2000). Eur. J. Org. Chem. pp. 3505-3510.]); Fritsky et al. (2001[Fritsky, I. O., Ott, R., Pritzkow, H. & Krämer, R. (2001). Chem. Eur. J. 7, 1221-1231.], 2003[Fritsky, I. O., Ott, R., Pritzkow, H. & Krämer, R. (2003). Inorg. Chim. Acta, 346, 111-118.]); Thompson (2002[Thompson, L. K. (2002). Coord. Chem. Rev. 233-234, 193-206.]); Wörl et al. (2005[Wörl, S., Pritzkow, H., Fritsky, I. O. & Krämer, R. (2005). Dalton Trans. pp. 27-29.]); Bauer-Siebenlist et al. (2005[Bauer-Siebenlist, B., Meyer, F., Farkas, E., Vidovic, D. & Dechert, S. (2005). Chem. Eur. J. 15, 4349-4360.]); Thallapally et al. (2010[Thallapally, P. K., Fernandez, C. A., Motkuri, R. K., Nune, S. K., Liub, J. & Pedenb, C. H. F. (2010). Dalton Trans. 39, 1692-1694.]); Cui et al. (2012[Cui, Y., Yue, Y., Qian, G. & Chen, B. (2012). Chem. Rev. 112, 1126-1162.]); Beauvais et al. (2000[Beauvais, L. G., Shores, M. P. & Long, J. R. (2000). J. Am. Chem. Soc. 122, 2763-2772.]). For studies of dinuclear copper(II) catecholase activity, see: Demmin et al. (1991[Demmin, T. R., Swerdloff, M. D. & Rogic, M. M. (1991). J. Am. Chem. Soc. 103, 5795-5804.]); Monzani et al. (1998[Monzani, E., Quinti, L., Perotti, A., Casella, L., Gulotti, M., Randaccio, L., Geremia, S., Nardin, G., Faleschini, P. & Tabbi, G. (1998). Inorg. Chem. 37, 553-562.]). For use of 2-hydroxyiminopropanoic acid derivatives as versatile ligands, see: Fritsky et al. (1998[Fritsky, I. O., Kozlowski, H., Sadler, P. J., Yefetova, O. P., Swiatek-Kozlowska, J., Kalibabchuk, V. A. & Glowiak, T. (1998). J. Chem. Soc. Dalton Trans. pp. 3269-3274.], 2006[Fritsky, I. O., Kozlowski, H., Kanderal, O. M., Haukka, M., Swiatek-Kozlowska, J., Gumienna-Kontecka, E. & Meyer, F. (2006). Chem. Commun. pp. 4125-4127.]); Kanderal et al. (2005[Kanderal, O. M., Kozlowski, H., Dobosz, A., Swiatek-Kozlowska, J., Meyer, F. & Fritsky, I. O. (2005). Dalton Trans. pp. 1428-1437.]); Moroz et al. (2008[Moroz, Y. S., Kulon, K., Haukka, M., Gumienna-Kontecka, E., Kozlowski, H., Meyer, F. & Fritsky, I. O. (2008). Inorg. Chem. 47, 5656-5665.], 2010[Moroz, Y. S., Szyrweil, L., Demeshko, S., Kozlowski, H., Meyer, F. & Fritsky, I. O. (2010). Inorg. Chem. 49, 4750-4752.], 2012[Moroz, Y. S., Demeshko, S., Haukka, M., Mokhir, A., Mitra, U., Stocker, M., Müller, P., Meyer, F. & Fritsky, I. O. (2012). Inorg. Chem. 51, 7445-7447.]); For the [tau] parameter, see: Addison et al. (1984[Addison, A. W., Rao, T. N., Reedijk, J., van Rijn, J. & Verschoor, G. C. (1984). J. Chem. Soc. Dalton Trans. pp. 1349-1356.]). For related structures, see: Duda et al. (1997[Duda, A. M., Karaczyn, A., Kozlowski, H., Fritsky, I. O., Glowiak, T., Prisyazhnaya, E. V., Sliva, T. Yu. & Swiatek-Kozlowska, J. (1997). J. Chem. Soc. Dalton Trans. pp. 3853-3859.]); Dobosz et al. (1999[Dobosz, A., Dudarenko, N. M., Fritsky, I. O., Glowiak, T., Karaczyn, A., Kozlowski, H., Sliva, T. Yu. & Swiatek-Kozlowska, J. (1999). J. Chem. Soc. Dalton Trans. pp. 743-749.]); Mokhir et al. (2002[Mokhir, A. A., Gumienna-Kontecka, E. S., Swiatek-Kozlowska, J., Petkova, E. G., Fritsky, I. O., Jerzykiewicz, L., Kapshuk, A. A. & Sliva, T. Yu. (2002). Inorg. Chim. Acta, 329, 113-121.]); Onindo et al. (1995[Onindo, C. O., Sliva, T. Yu., Kowalik-Jankowska, T., Fritsky, I. O., Buglyo, P., Pettit, L. D., Kozlowski, H. & Kiss, T. (1995). J. Chem. Soc. Dalton Trans. pp. 3911-3915.]); Petrusenko et al. (1997[Petrusenko, S. R., Kokozay, V. N. & Fritsky, I. O. (1997). Polyhedron, 16, 267-274.]); Sliva et al. (1997[Sliva, T. Yu., Kowalik-Jankowska, T., Amirkhanov, V. M., Glowiak, T., Onindo, C. O., Fritsky, I. O. & Kozlowski, H. (1997). J. Inorg. Biochem. 65, 287-294.]); Dvorkin et al. (1990a[Dvorkin, A. A., Fritskii, I. O., Simonov, I. A., Lampeka, R. D., Mazus, M. D. & Malinovskii, T. I. (1990a). Dokl. Akad. Nauk SSSR, 310, 87-90.],b[Dvorkin, A. A., Simonov, I. A., Skopenko, V. V., Fritskii, I. O. & Lampeka, R. D. (1990b). Dokl. Akad. Nauk SSSR, 313, 98-101.]); Lampeka et al. (1989[Lampeka, R. D., Dvorkin, A. A., Simonov, Y. A., Fritsky, I. O. & Skopenko, V. V. (1989). Ukr. Khim. Zh. 55, 458-461.]); Skopenko et al. (1990[Skopenko, V. V., Lampeka, R. D. & Fritskii, I. O. (1990). Dokl. Akad. Nauk SSSR, 312, 123-128.]). For carbon dioxide capture, see: Kovbasyuk et al. (1997[Kovbasyuk, L. A., Fritsky, I. O., Kokozay, V. N. & Iskenderov, T. S. (1997). Polyhedron, 16, 1723-1729.]); Pavlishchuk et al. (2002[Pavlishchuk, V., Birkelbach, F., Weyhermüller, T., Wieghardt, K. & Chaudhuri, P. (2002). Inorg. Chem. 41, 4405-4416.]); Nanda et al. (2006[Nanda, P. K., Bera, M., Aromí, G. & Ray, D. (2006). Polyhedron, 25, 2791-2799.]).

[Scheme 1]

Experimental

Crystal data
  • (C8H18N3O2)2[Cu2(C8H15N3O2)2(C8H17N3O2)2] (C9H16N3O4)2·2C2H3N

  • Mr = 1791.14

  • Triclinic, [P \overline 1]

  • a = 9.3077 (3) Å

  • b = 12.9458 (6) Å

  • c = 19.8381 (6) Å

  • [alpha] = 107.875 (1)°

  • [beta] = 98.461 (2)°

  • [gamma] = 92.718 (2)°

  • V = 2239.34 (14) Å3

  • Z = 1

  • Mo K[alpha] radiation

  • [mu] = 0.55 mm-1

  • T = 120 K

  • 0.17 × 0.14 × 0.11 mm

Data collection
  • Nonius KappaCCD diffractometer

  • Absorption correction: multi-scan (SORTAV; Blessing, 1995[Blessing, R. H. (1995). Acta Cryst. A51, 33-38.]) Tmin = 0.911, Tmax = 0.944

  • 32405 measured reflections

  • 9811 independent reflections

  • 7089 reflections with I > 2[sigma](I)

  • Rint = 0.074

Refinement
  • R[F2 > 2[sigma](F2)] = 0.053

  • wR(F2) = 0.147

  • S = 1.05

  • 9811 reflections

  • 545 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.78 e Å-3

  • [Delta][rho]min = -0.70 e Å-3

Table 1
Selected bond lengths (Å)

Cu1-N1 1.984 (2)
Cu1-N2 1.957 (2)
Cu1-N3 2.000 (2)
Cu1-N4 2.041 (2)
Cu1-O1i 2.441 (2)
Symmetry code: (i) -x+2, -y, -z+1.

Table 2
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O4-H4O...O2i 1.00 1.67 2.574 (3) 150
O6-H6O...O1ii 0.91 1.71 2.613 (3) 174
N3-H3A...O1ii 0.86 2.45 2.938 (3) 116
N3-H3B...O3 0.90 2.16 2.978 (3) 151
N4-H4C...O3 0.93 2.09 2.908 (3) 145
N4-H4D...O1 0.92 2.47 2.967 (3) 115
N4-H4D...N1ii 0.92 2.50 3.123 (3) 126
N7-H7D...O5iii 0.79 2.29 3.002 (3) 149
N7-H7D...O5 0.79 2.60 3.109 (3) 123
N7-H7E...O7iii 0.87 1.84 2.705 (3) 172
N7-H7F...O8iv 1.05 1.82 2.859 (3) 169
N7-H7F...O7iv 1.05 2.43 2.981 (3) 112
N10-H10N...N13v 0.98 2.27 3.107 (5) 143
N11-H11N...O7 0.90 1.95 2.773 (3) 151
O10-H10O...O8vi 0.86 1.77 2.626 (3) 169
Symmetry codes: (i) x, y+1, z; (ii) -x+2, -y, -z+1; (iii) -x+2, -y, -z; (iv) x+1, y, z; (v) -x+1, -y+1, -z; (vi) -x+1, -y, -z.

Data collection: COLLECT (Nonius, 2002[Nonius (2002). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: DENZO/SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: DIAMOND (Brandenburg, 2009[Brandenburg, K. (2009). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GG2096 ).


Acknowledgements

This work was supported by the Russian Fund for Basic Research (grants11-03-00262 and 11-03-90417), the Federal Targeted Program Scientific and Scientific-Pedagogical Personnel of Innovative Russia in 2009-2013 (contract P1294 from 09/06/2010) and the State Fund for Fundamental Research of Ukraine (grant No. F40.3/041). Financial support from the Visby Program through the Swedish Institute is gratefully acknowledged.

References

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Bauer-Siebenlist, B., Meyer, F., Farkas, E., Vidovic, D. & Dechert, S. (2005). Chem. Eur. J. 15, 4349-4360.
Beauvais, L. G., Shores, M. P. & Long, J. R. (2000). J. Am. Chem. Soc. 122, 2763-2772.  [ISI] [CrossRef] [ChemPort]
Blessing, R. H. (1995). Acta Cryst. A51, 33-38.  [CrossRef] [details]
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Cui, Y., Yue, Y., Qian, G. & Chen, B. (2012). Chem. Rev. 112, 1126-1162.  [ISI] [CrossRef] [ChemPort] [PubMed]
Demmin, T. R., Swerdloff, M. D. & Rogic, M. M. (1991). J. Am. Chem. Soc. 103, 5795-5804.  [CrossRef] [ISI]
Dobosz, A., Dudarenko, N. M., Fritsky, I. O., Glowiak, T., Karaczyn, A., Kozlowski, H., Sliva, T. Yu. & Swiatek-Kozlowska, J. (1999). J. Chem. Soc. Dalton Trans. pp. 743-749.  [CSD] [CrossRef]
Duda, A. M., Karaczyn, A., Kozlowski, H., Fritsky, I. O., Glowiak, T., Prisyazhnaya, E. V., Sliva, T. Yu. & Swiatek-Kozlowska, J. (1997). J. Chem. Soc. Dalton Trans. pp. 3853-3859.  [CSD] [CrossRef]
Dvorkin, A. A., Fritskii, I. O., Simonov, I. A., Lampeka, R. D., Mazus, M. D. & Malinovskii, T. I. (1990a). Dokl. Akad. Nauk SSSR, 310, 87-90.  [ChemPort]
Dvorkin, A. A., Simonov, I. A., Skopenko, V. V., Fritskii, I. O. & Lampeka, R. D. (1990b). Dokl. Akad. Nauk SSSR, 313, 98-101.  [ChemPort]
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Fritsky, I. O., Kozlowski, H., Sadler, P. J., Yefetova, O. P., Swiatek-Kozlowska, J., Kalibabchuk, V. A. & Glowiak, T. (1998). J. Chem. Soc. Dalton Trans. pp. 3269-3274.  [CSD] [CrossRef]
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Fritsky, I. O., Ott, R., Pritzkow, H. & Krämer, R. (2003). Inorg. Chim. Acta, 346, 111-118.  [ISI] [CSD] [CrossRef] [ChemPort]
Kanderal, O. M., Kozlowski, H., Dobosz, A., Swiatek-Kozlowska, J., Meyer, F. & Fritsky, I. O. (2005). Dalton Trans. pp. 1428-1437.  [CrossRef]
Kovbasyuk, L. A., Fritsky, I. O., Kokozay, V. N. & Iskenderov, T. S. (1997). Polyhedron, 16, 1723-1729.  [CrossRef] [ChemPort] [ISI]
Krämer, R. & Fritsky, I. O. (2000). Eur. J. Org. Chem. pp. 3505-3510.
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Moroz, Y. S., Kulon, K., Haukka, M., Gumienna-Kontecka, E., Kozlowski, H., Meyer, F. & Fritsky, I. O. (2008). Inorg. Chem. 47, 5656-5665.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
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Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.
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Petrusenko, S. R., Kokozay, V. N. & Fritsky, I. O. (1997). Polyhedron, 16, 267-274.  [CrossRef] [ChemPort] [ISI]
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Acta Cryst (2012). E68, m1480-m1481   [ doi:10.1107/S160053681204620X ]

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