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Volume 68 
Part 12 
Pages m1568-m1569  
December 2012  

Received 16 November 2012
Accepted 24 November 2012
Online 30 November 2012

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.004 Å
Disorder in main residue
R = 0.030
wR = 0.074
Data-to-parameter ratio = 12.9
Details
Open access

Diammine{N-[2-(hydroxyimino)propionyl]-N'-[2-(oxidoimino)propionyl]propane-1,3-diaminido-[kappa]4N,N',N'',N'''}iron(III)

aDepartment of Chemistry, National Taras Shevchenko University of Kyiv, Volodymyrska Street 64, 01601 Kyiv, Ukraine, and bDepartment of Chemistry, University of Jyvãskylã, PO Box 35, FI-40014, Finland
Correspondence e-mail: stefania.tomyn@gmail.com

In the title compound, [Fe(C9H13N4O4)(NH3)2], the FeIII atom, lying on a mirror plane, is coordinated by four N atoms of a triply deprotonated tetradentate N-[2-(hydroxyimino)propionyl]-N'-[2-(oxidoimino)propionyl]propane-1,3-diaminide ligand in the equatorial plane and two N atoms of two ammonia molecules at the axial positions in a distorted octahedral geometry. A short intramolecular O-H...O hydrogen bond between the cis-disposed oxime O atoms stabilizes the pseudo-macrocyclic configuration of the ligand. In the crystal, molecules are linked by N-H...O hydrogen bonds into a three-dimensional network. The ligand has a mirror-plane symmetry. One of the methylene groups of the propane bridge is disordered over two sets of sites with equal occupancy factors.

Related literature

For oximes as potential bridging ligands, see: 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.]); Skopenko et al. (1990[Skopenko, V. V., Lampeka, R. D. & Fritskii, I. O. (1990). Dokl. Akad. Nauk SSSR, 312, 123-128.]). For oximes stabilizing high oxidation states of metal ions, 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.]). For the coordination chemistry of tetradentate open-chain ligands derived from oximes and amides, 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.]); Fritsky et al. (2004[Fritsky, I. O., Swiatek-Kozlowska, J., Dobosz, A., Sliva, T. Y. & Dudarenko, N. M. (2004). Inorg. Chim. Acta, 357, 3746-3752.]); Kufelnicki et al. (2010[Kufelnicki, A., Tomyn, S. V., Nedelkov, R. V., Haukka, M., Jaciubek-Rosinska, J., Pajak, M., Jaszczak, J., Swiatek, M. & Fritsky, I. O. (2010). Inorg. Chim. Acta, 363, 2996-3003.]). For related structures, see: 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.]); Mokhir et al. (2002[Mokhir, A. A., Gumienna-Kontecka, E., 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.]); Sliva et al. (1997a[Sliva, T. Yu., Duda, A. M., Glowiak, T., Fritsky, I. O., Amirkhanov, V. M., Mokhir, A. A. & Kozlowski, H. (1997a). J. Chem. Soc. Dalton Trans. pp. 273-276.],b[Sliva, T. Yu., Kowalik-Jankowska, T., Amirkhanov, V. M., Glowiak, T., Onindo, C. O., Fritsky, I. O. & Kozlowski, H. (1997b). J. Inorg. Biochem. 65, 287-294.]).

[Scheme 1]

Experimental

Crystal data
  • [Fe(C9H13N4O4)(NH3)2]

  • Mr = 331.15

  • Monoclinic, P 21 /m

  • a = 8.9111 (3) Å

  • b = 7.2255 (3) Å

  • c = 10.6194 (4) Å

  • [beta] = 108.994 (2)°

  • V = 646.52 (4) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 1.19 mm-1

  • T = 100 K

  • 0.20 × 0.09 × 0.04 mm

Data collection
  • Nonius KappaCCD diffractometer

  • Absorption correction: multi-scan (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.]) Tmin = 0.795, Tmax = 0.954

  • 12359 measured reflections

  • 1599 independent reflections

  • 1361 reflections with I > 2[sigma](I)

  • Rint = 0.047

Refinement
  • R[F2 > 2[sigma](F2)] = 0.030

  • wR(F2) = 0.074

  • S = 1.04

  • 1599 reflections

  • 124 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.58 e Å-3

  • [Delta][rho]min = -0.46 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1O...O4 0.98 1.54 2.508 (3) 168
N5-H5D...O4i 0.91 2.15 3.015 (2) 158
N5-H5E...O2ii 0.91 2.11 2.979 (2) 160
N5-H5F...O3iii 0.91 2.10 2.969 (2) 160
Symmetry codes: (i) [-x+2, y+{\script{1\over 2}}, -z+1]; (ii) [-x+2, y+{\script{1\over 2}}, -z+2]; (iii) [-x+1, y+{\script{1\over 2}}, -z+1].

Data collection: COLLECT (Nonius, 2000[Nonius (2000). 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: XP in SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HY2607 ).


Acknowledgements

Financial support from the State Fund for Fundamental Researches of Ukraine (grant No. F40.3/041) is gratefully acknowledged.

References

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]
Fritsky, I. O., Kozlowski, H., Kanderal, O. M., Haukka, M., Swiatek-Kozlowska, J., Gumienna-Kontecka, E. & Meyer, F. (2006). Chem. Commun. pp. 4125-4127.  [CSD] [CrossRef]
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]
Fritsky, I. O., Swiatek-Kozlowska, J., Dobosz, A., Sliva, T. Y. & Dudarenko, N. M. (2004). Inorg. Chim. Acta, 357, 3746-3752.  [CrossRef] [ChemPort]
Kanderal, O. M., Kozlowski, H., Dobosz, A., Swiatek-Kozlowska, J., Meyer, F. & Fritsky, I. O. (2005). Dalton Trans. pp. 1428-1437.  [CrossRef]
Kufelnicki, A., Tomyn, S. V., Nedelkov, R. V., Haukka, M., Jaciubek-Rosinska, J., Pajak, M., Jaszczak, J., Swiatek, M. & Fritsky, I. O. (2010). Inorg. Chim. Acta, 363, 2996-3003.  [CrossRef] [ChemPort]
Lampeka, R. D., Dvorkin, A. A., Simonov, Y. A., Fritsky, I. O. & Skopenko, V. V. (1989). Ukr. Khim. Zh. 55, 458-461.  [ChemPort]
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.  [ISI] [CrossRef] [ChemPort] [details]
Mokhir, A. A., Gumienna-Kontecka, E., Swiatek-Kozlowska, J., Petkova, E. G., Fritsky, I. O., Jerzykiewicz, L., Kapshuk, A. A. & Sliva, T. Yu. (2002). Inorg. Chim. Acta, 329, 113-121.  [ISI] [CSD] [CrossRef] [ChemPort]
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]
Moroz, Y. S., Szyrweil, L., Demeshko, S., Kozlowski, H., Meyer, F. & Fritsky, I. O. (2010). Inorg. Chem. 49, 4750-4752.  [ISI] [CSD] [CrossRef] [ChemPort] [PubMed]
Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands.
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.  [CrossRef]
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.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Skopenko, V. V., Lampeka, R. D. & Fritskii, I. O. (1990). Dokl. Akad. Nauk SSSR, 312, 123-128.  [ChemPort]
Sliva, T. Yu., Duda, A. M., Glowiak, T., Fritsky, I. O., Amirkhanov, V. M., Mokhir, A. A. & Kozlowski, H. (1997a). J. Chem. Soc. Dalton Trans. pp. 273-276.  [CrossRef]
Sliva, T. Yu., Kowalik-Jankowska, T., Amirkhanov, V. M., Glowiak, T., Onindo, C. O., Fritsky, I. O. & Kozlowski, H. (1997b). J. Inorg. Biochem. 65, 287-294.  [CrossRef] [ChemPort] [ISI]


Acta Cryst (2012). E68, m1568-m1569   [ doi:10.1107/S160053681204826X ]

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