Diammine{N-[2-(hy­droxy­imino)­propion­yl]-N′-[2-(oxidoimino)­propion­yl]propane-1,3-diaminido-κ4N,N′,N′′,N′′′}iron(III)

Tomyn, S.; Haukka, M.; Nedelkov, R.

doi:10.1107/S160053681204826X

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 12| December 2012| Pages m1568-m1569

doi:10.1107/S160053681204826X

Open

access

Diammine{N-[2-(hydroxyimino)propionyl]-N′-[2-(oxidoimino)propionyl]propane-1,3-diaminido-κ⁴N,N′,N′′,N′′′}iron(III)

Stefania Tomyn,^a ^* Matti Haukka ^b and Ruslan Nedelkov ^a

^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

(Received 16 November 2012; accepted 24 November 2012; online 30 November 2012)

In the title compound, [Fe(C₉H₁₃N₄O₄)(NH₃)₂], the Fe^III 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 , 2010 ); Skopenko et al. (1990 ). For oximes stabilizing high oxidation states of metal ions, see: Fritsky et al. (1998 , 2006 ); Kanderal et al. (2005 ). For the coordination chemistry of tetradentate open-chain ligands derived from oximes and amides, see: Duda et al. (1997 ); Fritsky et al. (2004 ); Kufelnicki et al. (2010 ). For related structures, see: Dvorkin et al. (1990a ,b ); Lampeka et al. (1989 ); Mokhir et al. (2002 ); Onindo et al. (1995 ); Sliva et al. (1997a ,b ).

Experimental

Crystal data

[Fe(C₉H₁₃N₄O₄)(NH₃)₂]
M_r = 331.15
Monoclinic, P 2₁ /m
a = 8.9111 (3) Å
b = 7.2255 (3) Å
c = 10.6194 (4) Å
β = 108.994 (2)°
V = 646.52 (4) Å³
Z = 2
Mo Kα radiation
μ = 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 ) T_min = 0.795, T_max = 0.954
12359 measured reflections
1599 independent reflections
1361 reflections with I > 2σ(I)
R_int = 0.047

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.074
S = 1.04
1599 reflections
124 parameters
H-atom parameters constrained
Δρ_max = 0.58 e Å⁻³
Δρ_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 ); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO/SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2006 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681204826X/hy2607sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681204826X/hy2607Isup2.hkl

checkCIF report

Comment top

Polydentate oxime ligands containing both oxime and other donor functions (e.g. carboxylic, amide, hydroxamic) draw considerable attention during past two decades due to their potential for the bridging mode of coordination and mediation of strong magnetic exchange interactions between metal ions (Moroz et al., 2008, 2010; Skopenko et al., 1990) and for the preparation of metal complexes with efficient stabilization of unusually high oxidation states of 3d-metal ions (Fritsky et al., 1998, 2006; Kanderal et al., 2005). The open-chain tetradentate oxime-and-amide ligands were the subjects of several studies carried out in our group, and a series of mono- and polynuclear complexes of copper(III), nickel(II) and cobalt(III) have been reported within past 15 years (Duda et al., 1997; Fritsky et al., 2004, 2006; Kanderal et al., 2005; Kufelnicki et al., 2010). As a part of our research study of open-chain tetradentate oxime-and-amide ligands, we present the structure of the title compound containing iron(III) as a central atom.

In the title compound, Fe^III ion, lying on a mirror plane, is coordinated by four N atoms of a triply deprotonated tetradentate ligand, N,N'-bis(2-hydroxyiminopropionyl)propane-1,3-diamine, in the equatorial plane and by two N atoms of two ammonia molecules at the axial postions in a distorted octahedral geometry (Fig. 1). The tetradentate ligand coordinates the Fe^III atom in a planar fashion, forming three condensed 5-, 6- and 5-membered chelate rings. All angles around the Fe^III atom deviate insignificantly from 90°. There are no alternating deviations for N(oxime) and N(amide) atoms from the N1, N2, N3 and N4 plane. The values of Fe—N(amide) and Fe—N(oxime) bond lengths in the equatorial plane are in the range of 1.909 (2)–1.917 (2) Å. The distance between the Fe^III atom and the two axial N atom is 1.993 (3) Å. Bond lengths of N—C and C═O of the amide groups are 1.323 (3)–1.327 (3) and 1.252 (3)–1.255 (3) Å, respectively, and are typical for the deprotonated amide groups (Dvorkin et al., 1990a, b; Lampeka et al., 1989; Onindo et al., 1995). The bond lengths N—O and C═N of the oxime groups are 1.349 (3)–1.364 (3) and 1.291 (3)–1.292 (3) Å, respectively, that is typical for the amide derivatives of 2-hydroxypropanoic acid (Duda et al., 1997; Mokhir et al., 2002; Onindo et al., 1995; Sliva et al., 1997a, b). In the crystal, the complex molecules are linked by intermolecular N—H···O hydrogen bonds formed between the coordinated ammonia molecules and O atoms of the ligand into a three-dimensional network (Fig. 2). An intramolecular O—H···O hydrogen bond is also present. One of the methylene groups of the propane bridge is disordered in a 0.5:0.5 ratio.

Related literature top

For oximes as potential bridging ligands, see: Moroz et al. (2008, 2010); Skopenko et al. (1990). For oximes stabilizing high oxidation states of metal ions, see: Fritsky et al. (1998, 2006); Kanderal et al. (2005). For coordination chemistry of tetradentate oxime-and-amide open-chain ligands, see: Duda et al. (1997); Fritsky et al. (2004); Kufelnicki et al. (2010). For related structures, see: Dvorkin et al. (1990a,b); Lampeka et al. (1989); Mokhir et al. (2002); Onindo et al. (1995); Sliva et al. (1997a,b).

Experimental top

Fe(ClO₄).6H₂O (0.363 g, 1 mmol) was dissolved in 5 ml of DMSO and added to a solution of N,N'-bis(2-hydroxyiminopropionyl)propane-1,3-diamine (0.246 g, 1 mmol) in 10 ml of DMSO. The resulting deep orange mixture was stirred for 15 min at room temperature, filtered off and set aside for crystallization at ambient conditions in an ammonia atmosphere. Red insoluble crystals of the title compound suitable for X-ray analysis were obtained in 24 h (yield: 0.227 g, 68%). Analysis, calculated for C₉H₁₉FeN₆O₄: C 39.27, H 6.96, N 30.53%; found: C 39.59, H 7.02, N 30.84%.

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO/SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level. C5 atom and all C-bound H atoms are disordered over two sets of sites across the mirror plane with equal occupancies. [Symmetry code: (i) x, 3/2-y, z.]
	Fig. 2. A packing diagram of the title compound. Hydrogen bonds are indicated by dashed lines. H atoms not involved in hydrogen bonds have been omitted for clarity.

Diammine{N-[2-(hydroxyimino)propionyl]-N'-[2- (oxidoimino)propionyl]propane-1,3-diaminido- κ⁴N,N',N'',N'''}iron(III) top

Crystal data top

[Fe(C₉H₁₃N₄O₄)(NH₃)₂]	F(000) = 346.0
M_r = 331.15	D_x = 1.701 Mg m⁻³
Monoclinic, P2₁/m	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yb	Cell parameters from 2700 reflections
a = 8.9111 (3) Å	θ = 1.0–27.5°
b = 7.2255 (3) Å	µ = 1.19 mm⁻¹
c = 10.6194 (4) Å	T = 100 K
β = 108.994 (2)°	Block, red
V = 646.52 (4) Å³	0.20 × 0.09 × 0.04 mm
Z = 2

Data collection top

Nonius KappaCCD diffractometer	1599 independent reflections
Radiation source: fine-focus sealed tube	1361 reflections with I > 2σ(I)
Horizontally mounted graphite crystal monochromator	R_int = 0.047
Detector resolution: 9 pixels mm^-1	θ_max = 27.5°, θ_min = 2.4°
ϕ and ω scans with κ offset	h = −11→11
Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997)	k = −9→9
T_min = 0.795, T_max = 0.954	l = −13→13
12359 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.074	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.028P)² + 0.7141P] where P = (F_o² + 2F_c²)/3
1599 reflections	(Δ/σ)_max < 0.001
124 parameters	Δρ_max = 0.58 e Å⁻³
0 restraints	Δρ_min = −0.46 e Å⁻³

Crystal data top

[Fe(C₉H₁₃N₄O₄)(NH₃)₂]	V = 646.52 (4) Å³
M_r = 331.15	Z = 2
Monoclinic, P2₁/m	Mo Kα radiation
a = 8.9111 (3) Å	µ = 1.19 mm⁻¹
b = 7.2255 (3) Å	T = 100 K
c = 10.6194 (4) Å	0.20 × 0.09 × 0.04 mm
β = 108.994 (2)°

Data collection top

Nonius KappaCCD diffractometer	1599 independent reflections
Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997)	1361 reflections with I > 2σ(I)
T_min = 0.795, T_max = 0.954	R_int = 0.047
12359 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	0 restraints
wR(F²) = 0.074	H-atom parameters constrained
S = 1.04	Δρ_max = 0.58 e Å⁻³
1599 reflections	Δρ_min = −0.46 e Å⁻³
124 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Fe1	0.84000 (4)	0.7500	0.68148 (4)	0.01316 (12)
O1	1.1762 (2)	0.7500	0.72129 (19)	0.0199 (4)
H1O	1.1180	0.7500	0.6258	0.030*
O2	0.9831 (2)	0.7500	1.07989 (18)	0.0220 (4)
O3	0.4412 (2)	0.7500	0.36943 (19)	0.0196 (4)
O4	0.9952 (2)	0.7500	0.48443 (18)	0.0162 (4)
N5	0.85135 (18)	1.0255 (2)	0.67972 (15)	0.0151 (3)
H5D	0.9063	1.0618	0.6252	0.023*
H5E	0.9016	1.0674	0.7637	0.023*
H5F	0.7514	1.0730	0.6494	0.023*
N1	1.0616 (3)	0.7500	0.7808 (2)	0.0148 (4)
N2	0.8273 (3)	0.7500	0.8580 (2)	0.0149 (4)
N3	0.6183 (3)	0.7500	0.5839 (2)	0.0146 (4)
N4	0.8536 (2)	0.7500	0.5050 (2)	0.0135 (4)
C1	1.1043 (3)	0.7500	0.9092 (3)	0.0166 (5)
C2	1.2708 (3)	0.7500	0.9983 (3)	0.0243 (6)
H2A	1.2741	0.7215	1.0894	0.036*	0.50
H2B	1.3177	0.8722	0.9964	0.036*	0.50
H2C	1.3310	0.6563	0.9681	0.036*	0.50
C3	0.9631 (3)	0.7500	0.9576 (3)	0.0162 (5)
C4	0.6775 (3)	0.7500	0.8870 (3)	0.0191 (6)
H4A	0.6940	0.8119	0.9736	0.023*	0.50
H4B	0.6456	0.6205	0.8952	0.023*	0.50
C5	0.5460 (4)	0.8461 (6)	0.7819 (4)	0.0181 (8)	0.50
H5A	0.5811	0.9733	0.7708	0.022*	0.50
H5B	0.4534	0.8564	0.8136	0.022*	0.50
C6	0.4926 (3)	0.7500	0.6449 (3)	0.0187 (6)
H6A	0.4618	0.6207	0.6555	0.022*	0.50
H6B	0.3981	0.8145	0.5852	0.022*	0.50
C7	0.5789 (3)	0.7500	0.4522 (3)	0.0152 (5)
C8	0.7221 (3)	0.7500	0.4066 (3)	0.0152 (5)
C9	0.7113 (3)	0.7500	0.2641 (3)	0.0229 (6)
H9A	0.7349	0.8742	0.2386	0.034*	0.50
H9B	0.6038	0.7142	0.2092	0.034*	0.50
H9C	0.7880	0.6616	0.2505	0.034*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe1	0.01225 (19)	0.0146 (2)	0.01244 (19)	0.000	0.00372 (14)	0.000
O1	0.0132 (9)	0.0290 (11)	0.0181 (10)	0.000	0.0062 (8)	0.000
O2	0.0250 (10)	0.0279 (11)	0.0107 (9)	0.000	0.0027 (8)	0.000
O3	0.0121 (9)	0.0254 (11)	0.0183 (10)	0.000	0.0006 (7)	0.000
O4	0.0119 (8)	0.0212 (10)	0.0174 (9)	0.000	0.0073 (7)	0.000
N5	0.0155 (7)	0.0153 (8)	0.0139 (7)	0.0005 (6)	0.0041 (6)	0.0013 (6)
N1	0.0135 (10)	0.0150 (11)	0.0162 (11)	0.000	0.0052 (8)	0.000
N2	0.0150 (10)	0.0172 (11)	0.0131 (10)	0.000	0.0052 (8)	0.000
N3	0.0128 (10)	0.0175 (11)	0.0142 (11)	0.000	0.0053 (8)	0.000
N4	0.0120 (10)	0.0139 (11)	0.0153 (11)	0.000	0.0053 (8)	0.000
C1	0.0172 (13)	0.0147 (13)	0.0147 (12)	0.000	0.0007 (10)	0.000
C2	0.0201 (14)	0.0317 (17)	0.0174 (14)	0.000	0.0011 (11)	0.000
C3	0.0201 (13)	0.0128 (12)	0.0134 (12)	0.000	0.0025 (10)	0.000
C4	0.0181 (13)	0.0229 (14)	0.0181 (13)	0.000	0.0086 (11)	0.000
C5	0.0158 (17)	0.020 (2)	0.0206 (19)	0.0000 (15)	0.0091 (15)	0.0001 (15)
C6	0.0135 (12)	0.0250 (15)	0.0187 (13)	0.000	0.0067 (10)	0.000
C7	0.0147 (12)	0.0127 (12)	0.0174 (12)	0.000	0.0042 (10)	0.000
C8	0.0153 (12)	0.0157 (12)	0.0146 (12)	0.000	0.0048 (10)	0.000
C9	0.0190 (14)	0.0350 (17)	0.0124 (13)	0.000	0.0022 (11)	0.000

Geometric parameters (Å, º) top

Fe1—N3	1.909 (2)	N4—O4ⁱ	1.349 (3)
Fe1—N1	1.912 (2)	C1—C2	1.478 (4)
Fe1—N2	1.914 (2)	C1—C3	1.506 (4)
Fe1—N4	1.917 (2)	C2—H2A	0.9800
Fe1—N5	1.9932 (16)	C2—H2B	0.9800
O1—N1	1.364 (3)	C2—H2C	0.9800
O1—H1O	0.9769	C4—C5	1.500 (4)
O2—C3	1.252 (3)	C4—H4A	0.9900
O3—C7	1.255 (3)	C4—H4B	0.9900
O4—O4ⁱ	0.000 (4)	C5—C6	1.541 (4)
O4—N4	1.349 (3)	C5—H5A	0.9900
N5—H5D	0.9100	C5—H5B	0.9900
N5—H5E	0.9100	C6—H6A	0.9900
N5—H5F	0.9100	C6—H6B	0.9900
N1—C1	1.291 (3)	C7—C8	1.505 (4)
N2—C3	1.323 (3)	C8—C9	1.485 (4)
N2—C4	1.464 (3)	C9—H9A	0.9800
N3—C7	1.327 (3)	C9—H9B	0.9800
N3—C6	1.465 (3)	C9—H9C	0.9800
N4—C8	1.292 (3)

N3—Fe1—N1	179.44 (10)	C1—C2—H2A	109.5
N3—Fe1—N2	98.66 (9)	C1—C2—H2B	109.5
N1—Fe1—N2	80.78 (9)	H2A—C2—H2B	109.5
N3—Fe1—N4	81.55 (9)	C1—C2—H2C	109.5
N1—Fe1—N4	99.01 (9)	H2A—C2—H2C	109.5
N2—Fe1—N4	179.79 (9)	H2B—C2—H2C	109.5
N3—Fe1—N5	92.39 (4)	O2—C3—N2	127.8 (3)
N1—Fe1—N5	87.63 (5)	O2—C3—C1	120.1 (2)
N2—Fe1—N5	91.64 (5)	N2—C3—C1	112.0 (2)
N4—Fe1—N5	88.35 (5)	N2—C4—C5	112.9 (2)
N3—Fe1—N5ⁱ	92.39 (5)	N2—C4—H4A	109.0
N1—Fe1—N5ⁱ	87.63 (4)	C5—C4—H4A	109.0
N2—Fe1—N5ⁱ	91.64 (5)	N2—C4—H4B	109.0
N4—Fe1—N5ⁱ	88.35 (5)	C5—C4—H4B	109.0
N5—Fe1—N5ⁱ	173.75 (9)	H4A—C4—H4B	107.8
N1—O1—H1O	104.8	C4—C5—C6	114.8 (3)
Fe1—N5—H5D	109.5	C4—C5—H5A	108.6
Fe1—N5—H5E	109.5	C6—C5—H5A	108.6
H5D—N5—H5E	109.5	C4—C5—H5B	108.6
Fe1—N5—H5F	109.5	C6—C5—H5B	108.6
H5D—N5—H5F	109.5	H5A—C5—H5B	107.5
H5E—N5—H5F	109.5	N3—C6—C5	111.8 (2)
C1—N1—O1	118.8 (2)	N3—C6—H6A	109.3
C1—N1—Fe1	118.60 (18)	C5—C6—H6A	109.3
O1—N1—Fe1	122.60 (16)	N3—C6—H6B	109.3
C3—N2—C4	119.4 (2)	C5—C6—H6B	109.3
C3—N2—Fe1	116.91 (18)	H6A—C6—H6B	107.9
C4—N2—Fe1	123.68 (17)	O3—C7—N3	127.0 (2)
C7—N3—C6	119.2 (2)	O3—C7—C8	120.8 (2)
C7—N3—Fe1	116.37 (17)	N3—C7—C8	112.2 (2)
C6—N3—Fe1	124.43 (17)	N4—C8—C9	124.4 (2)
C8—N4—O4ⁱ	121.3 (2)	N4—C8—C7	112.4 (2)
C8—N4—O4	121.3 (2)	C9—C8—C7	123.2 (2)
C8—N4—Fe1	117.49 (18)	C8—C9—H9A	109.5
O4ⁱ—N4—Fe1	121.24 (16)	C8—C9—H9B	109.5
O4—N4—Fe1	121.24 (16)	H9A—C9—H9B	109.5
N1—C1—C2	124.4 (3)	C8—C9—H9C	109.5
N1—C1—C3	111.7 (2)	H9A—C9—H9C	109.5
C2—C1—C3	123.9 (2)	H9B—C9—H9C	109.5

N5—Fe1—N1—C1	92.04 (4)	N5—Fe1—N4—C8	−92.66 (4)
N5ⁱ—Fe1—N1—C1	−92.04 (4)	N5ⁱ—Fe1—N4—C8	92.66 (4)
N5—Fe1—N1—O1	−87.96 (4)	N5—Fe1—N4—O4ⁱ	87.34 (4)
N5ⁱ—Fe1—N1—O1	87.96 (4)	N5ⁱ—Fe1—N4—O4ⁱ	−87.34 (4)
N5—Fe1—N2—C3	−87.34 (4)	N5—Fe1—N4—O4	87.34 (4)
N5ⁱ—Fe1—N2—C3	87.34 (4)	N5ⁱ—Fe1—N4—O4	−87.34 (4)
N5—Fe1—N2—C4	92.66 (4)	C3—N2—C4—C5	149.83 (18)
N5ⁱ—Fe1—N2—C4	−92.66 (4)	Fe1—N2—C4—C5	−30.17 (18)
N5—Fe1—N3—C7	87.98 (5)	N2—C4—C5—C6	66.1 (3)
N5ⁱ—Fe1—N3—C7	−87.98 (5)	C7—N3—C6—C5	−150.96 (17)
N5—Fe1—N3—C6	−92.02 (5)	Fe1—N3—C6—C5	29.04 (17)
N5ⁱ—Fe1—N3—C6	92.02 (5)	C4—C5—C6—N3	−65.3 (3)

Symmetry code: (i) x, −y+3/2, z.

Hydrogen-bond geometry (Å, º) top

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···O4ⁱⁱ	0.91	2.15	3.015 (2)	158
N5—H5E···O2ⁱⁱⁱ	0.91	2.11	2.979 (2)	160
N5—H5F···O3^iv	0.91	2.10	2.969 (2)	160

Symmetry codes: (ii) −x+2, y+1/2, −z+1; (iii) −x+2, y+1/2, −z+2; (iv) −x+1, y+1/2, −z+1.

Experimental details

Crystal data
Chemical formula	[Fe(C₉H₁₃N₄O₄)(NH₃)₂]
M_r	331.15
Crystal system, space group	Monoclinic, P2₁/m
Temperature (K)	100
a, b, c (Å)	8.9111 (3), 7.2255 (3), 10.6194 (4)
β (°)	108.994 (2)
V (Å³)	646.52 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.19
Crystal size (mm)	0.20 × 0.09 × 0.04

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997)
T_min, T_max	0.795, 0.954
No. of measured, independent and observed [I > 2σ(I)] reflections	12359, 1599, 1361
R_int	0.047
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.074, 1.04
No. of reflections	1599
No. of parameters	124
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.58, −0.46

Computer programs: COLLECT (Nonius, 2000), DENZO/SCALEPACK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2006).

Hydrogen-bond geometry (Å, º) top

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+1/2, −z+1; (ii) −x+2, y+1/2, −z+2; (iii) −x+1, y+1/2, −z+1.

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., Kozłowski, H., Fritsky, I. O., Głowiak, T., Prisyazhnaya, E. V., Sliva, T. Yu. & Świątek-Kozłowska, J. (1997). J. Chem. Soc. Dalton Trans. pp. 3853–3859. CSD CrossRef Web of Science Google Scholar
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. CAS Google Scholar
Dvorkin, A. A., Simonov, I. A., Skopenko, V. V., Fritskii, I. O. & Lampeka, R. D. (1990b). Dokl. Akad. Nauk SSSR, 313, 98–101. CAS Google Scholar
Fritsky, I. O., Kozłowski, H., Kanderal, O. M., Haukka, M., Świątek-Kozłowska, J., Gumienna-Kontecka, E. & Meyer, F. (2006). Chem. Commun. pp. 4125–4127. Web of Science CSD CrossRef Google Scholar
Fritsky, I. O., Kozłowski, H., Sadler, P. J., Yefetova, O. P., Świątek-Kozłowska, J., Kalibabchuk, V. A. & Głowiak, T. (1998). J. Chem. Soc. Dalton Trans. pp. 3269–3274. Web of Science CSD CrossRef Google Scholar
Fritsky, I. O., Świątek-Kozłowska, J., Dobosz, A., Sliva, T. Y. & Dudarenko, N. M. (2004). Inorg. Chim. Acta, 357, 3746–3752. Web of Science CSD CrossRef CAS Google Scholar
Kanderal, O. M., Kozłowski, H., Dobosz, A., Świątek-Kozłowska, J., Meyer, F. & Fritsky, I. O. (2005). Dalton Trans. pp. 1428–1437. Web of Science CrossRef PubMed Google Scholar
Kufelnicki, A., Tomyn, S. V., Nedelkov, R. V., Haukka, M., Jaciubek-Rosińska, J., Pająk, M., Jaszczak, J., Świątek, M. & Fritsky, I. O. (2010). Inorg. Chim. Acta, 363, 2996–3003. Web of Science CSD CrossRef CAS Google Scholar
Lampeka, R. D., Dvorkin, A. A., Simonov, Y. A., Fritsky, I. O. & Skopenko, V. V. (1989). Ukr. Khim. Zh. 55, 458–461. CAS Google Scholar
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. Web of Science CrossRef CAS IUCr Journals Google Scholar
Mokhir, A. A., Gumienna-Kontecka, E., Świątek-Kozłowska, J., Petkova, E. G., Fritsky, I. O., Jerzykiewicz, L., Kapshuk, A. A. & Sliva, T. Yu. (2002). Inorg. Chim. Acta, 329, 113–121. Web of Science CSD CrossRef CAS Google Scholar
Moroz, Y. S., Kulon, K., Haukka, M., Gumienna-Kontecka, E., Kozłowski, H., Meyer, F. & Fritsky, I. O. (2008). Inorg. Chem. 47, 5656–5665. Web of Science CSD CrossRef PubMed CAS Google Scholar
Moroz, Y. S., Szyrweil, L., Demeshko, S., Kozłowski, H., Meyer, F. & Fritsky, I. O. (2010). Inorg. Chem. 49, 4750–4752. Web of Science CSD CrossRef CAS PubMed Google Scholar
Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands. Google Scholar
Onindo, C. O., Sliva, T. Yu., Kowalik-Jankowska, T., Fritsky, I. O., Buglyo, P., Pettit, L. D., Kozłowski, H. & Kiss, T. (1995). J. Chem. Soc. Dalton Trans. pp. 3911–3915. CrossRef Web of Science Google Scholar
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. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Skopenko, V. V., Lampeka, R. D. & Fritskii, I. O. (1990). Dokl. Akad. Nauk SSSR, 312, 123–128. CAS Google Scholar
Sliva, T. Yu., Duda, A. M., Głowiak, T., Fritsky, I. O., Amirkhanov, V. M., Mokhir, A. A. & Kozłowski, H. (1997a). J. Chem. Soc. Dalton Trans. pp. 273–276. CSD CrossRef Web of Science Google Scholar
Sliva, T. Yu., Kowalik-Jankowska, T., Amirkhanov, V. M., Głowiak, T., Onindo, C. O., Fritsky, I. O. & Kozłowski, H. (1997b). J. Inorg. Biochem. 65, 287–294. CSD CrossRef CAS Web of Science Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.