Crystal structure of tetra­aqua­[2-(pyridin-2-yl)-1H-imidazole-κ2N2,N3]iron(II) sulfate

Setifi, Z.; Setifi, F.; Francuski, B.M.; Novaković, S.B.; Merazig, H.

doi:10.1107/S2056989015004417

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Volume 71| Part 4| April 2015| Pages 346-349

doi:10.1107/S2056989015004417

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Crystal structure of tetraaqua[2-(pyridin-2-yl)-1H-imidazole-κ²N²,N³]iron(II) sulfate

Zouaoui Setifi,^a,^b Fatima Setifi,^a ^* Bojana M. Francuski,^c Sladjana B. Novaković ^c and Hocine Merazig ^b

^aLaboratoire de Chimie, Ingénierie Moléculaire et Nanostructures (LCIMN), Université Ferhat Abbas Sétif 1, Sétif 19000, Algeria, ^bUnité de Recherche de Chimie de l'Environnement et Moléculaire Structurale (CHEMS), Université Constantine 1, Constantine 25000, Algeria, and ^cVinča Institute of Nuclear Sciences, Laboratory of Theoretical Physics and Condensed Matter Physics, PO Box 522, University of Belgrade, 11001 Belgrade, Serbia
^*Correspondence e-mail: fat_setifi@yahoo.fr

Edited by M. Weil, Vienna University of Technology, Austria (Received 25 February 2015; accepted 3 March 2015; online 11 March 2015)

In the title compound, [Fe(C₈H₇N₃)(H₂O)₄]SO₄, the central Fe^II ion is octahedrally coordinated by two N atoms from the bidentate 2-(pyridin-2-yl)-1H-imidazole ligand and by four O atoms of the aqua ligands. The largest deviation from the ideal octahedral geometry is reflected by the small N—Fe—N bite angle of 76.0 (1)°. The Fe—N coordination bonds have markedly different lengths [2.1361 (17) and 2.243 (2) Å], with the shorter one to the pyrimidine N atom. The four Fe—O coordination bond lengths vary from 2.1191 (18) to 2.1340 (17) Å. In the crystal, the cations and anions are arranged by means of medium-strength O—H⋯O hydrogen bonds into layers parallel to the ab plane. Neighbouring layers further interconnect by N—H⋯O hydrogen bonds involving the imidazole fragment as donor group to one sulfate O atom as an acceptor. The resulting three-dimensional network is consolidated by C—H⋯O, C—H⋯π and π–π interactions.

Keywords: crystal structure; 2-(pyridin-2-yl)-1H-imidazole; iron(II) complex; hydrogen bonding; C—H⋯π interactions; π–π interactions.

CCDC reference: 1051905

1. Chemical context

Polynitrile anions have recently received considerable attention in the fields of coordination chemistry and molecular materials (Benmansour et al., 2010 ). These organic anions are of interest due to their ability to act towards metal atoms with various coordination modes and for their high degree of electronic delocalization (Miyazaki et al., 2003 ; Atmani et al., 2008 ; Benmansour et al., 2008 , 2012 ; Setifi et al., 2002 , 2013 , 2014 ; Addala et al., 2015 ).

We are interested in using these anionic ligands in combination with other neutral bridging co-ligands to explore their structural features and properties relevant to the field of molecular materials exhibiting the spin crossover (SCO) phenomenon (Dupouy et al., 2008 , 2009 ). In an attempt to prepare such an iron(II) complex using hydrothermal synthesis, we obtained instead the title compound [Fe(pyim)(H₂O)₄]SO₄, (I), where pyim is 2-(pyridin-2-yl)-1H-imidazole.

2. Structural commentary

Fig. 1 shows the asymmetric unit of (I). The main building units in the crystal structure of (I) are octahedral [Fe(pyim)(H₂O)₄]²⁺ complex cations and [SO₄]²⁻ anions. The distorted octahedral environment of the central Fe^II ion is defined by two N donor atoms of the pyim ligand and by the O atoms of two water molecules in the equatorial plane, while the two remaining water molecules coordinate at the axial sites. The bite angle N1—Fe—N2 of 76.04 (7)° shows the most significant deviation from the ideal octahedral geometry, with the other coordination angles deviating by 0.21 (7) to 11.91 (7)°.

Figure 1
The molecular structure of (I)

, with atom labels and displacement ellipsoids at the 50% probability level. Hydrogen bonds are shown as double dashed lines.

The Fe—N coordination bonds with the chelate ligand have markedly different lengths, Fe—N1 = 2.243 (2) and Fe—N2 = 2.1361 (17) Å, which are also dissimilar to those in the previously reported [Fe(dmbpy)(H₂O)₄]SO₄ complex where dmbpy is 5,5′-dimethyl-2,2′-bipyridine (Belamri et al., 2014 .) comprising a nearly symmetrical dipyridyl ligand [Fe—N = 2.176 (3) Å on average]. The torsion angles within the approximately planar five-membered chelate ring of (I) vary from 0.6 (3) to −5.2 (2)° and reflect a more pronounced deviation from planarity in comparison with the dmbpy Fe^II complex that exhibits a maximal torsion angle of 2.0 (3)°. The dihedral angle of 5.5 (1) ° between the aromatic rings of the pyim ligand is within the range of the values reported for the eight independent molecules in the crystal structure of the non-coordinating ligand [1(1) to 17 (1)°; Tinant et al., 2010 ]. In the present complex, all four Fe—O bond lengths, ranging from 2.1191 (18) to 2.1340 (17) Å, are longer than the corresponding ones in the [Fe(dmbpy)(H₂O)₄]SO₄ complex, which range from 2.079 (2) to 2.110 (2) Å.

3. Supramolecular features

The crystal packing of (I) is stabilized by a complex hydrogen-bonding network involving the coordinating water molecules and the imidazole fragment as donors to the O acceptors atoms of the sulfate anion. Each cationic [Fe(pyim)(H₂O)₄]²⁺ unit is surrounded by five [SO₄]²⁻ anions. Similarly to the crystal structure of [Fe(dmbpy)(H₂O)₄]SO₄, pairs of axially and equatorially coordinating water molecules bind to pairs of O acceptor atoms from the same [SO₄]²⁻ group, forming eight medium-strength interactions (Table 1). These hydrogen bonds arrange the complex molecules into layers parallel to the ab plane (Fig. 2). Additional N—H⋯O and C—H⋯O hydrogen bonds involving the donors from the aromatic ligand interconnect adjacent layers into a three-dimensional arrangement (Fig. 3). The vicinity of aromatic rings in the inter-layer region gives rise to C—H⋯π [H3⋯Cg1ⁱ = 3.033 Å; C3—H3⋯Cg1ⁱ = 117°; symmetry code: (i) = −x + $[{1\over 2}]$ , y + $[{1\over 2}]$ , z; Cg1 is the centroid of the imidazole ring] and weak π–π interactions [Cg1⋯Cg2ⁱⁱ = 3.821 Å, the shortest interatomic distance N3⋯C2ⁱⁱ = 3.325 (1) Å; symmetry code: (ii) = −x + 1, −y + 1, −z + 1; Cg1 and Cg2 are the centroids of the imidazole and pyridine rings, respectively]. C—H⋯O interactions are also observed (Table 1).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H1O5⋯O3ⁱ	0.78 (3)	2.00 (3)	2.785 (3)	175 (3)
O5—H2O5⋯O1ⁱⁱ	0.85 (4)	2.00 (3)	2.845 (3)	172 (4)
O6—H1O6⋯O1	0.71 (3)	2.15 (3)	2.857 (3)	170 (3)
O6—H2O6⋯O3ⁱⁱⁱ	0.89 (3)	1.85 (3)	2.736 (3)	175 (3)
O7—H1O7⋯O1ⁱⁱⁱ	0.64 (4)	2.17 (3)	2.809 (3)	173 (4)
O7—H2O7⋯O4ⁱⁱ	0.90 (4)	1.83 (3)	2.720 (3)	168 (4)
O8—H1O8⋯O4ⁱ	0.76 (3)	1.96 (3)	2.722 (3)	178 (4)
O8—H2O8⋯O2	0.84 (3)	1.90 (3)	2.737 (3)	175 (3)
N3—H3N⋯O2^iv	0.93 (3)	1.93 (3)	2.858 (3)	178 (3)
C4—H4⋯O2^iv	0.93	2.40	3.287 (3)	160
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, z]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[x-{\script{1\over 2}}, y, -z+{\script{1\over 2}}]$ ; (iv) -x+1, -y+1, -z+1.

Figure 2
O—H⋯O interactions (dashed lines) connect cationic and anionic units into layers parallel to the ab plane (view of a single layer down the c axis). H atoms not involved in hydrogen bonding have been omitted for the sake of clarity.

Figure 3
The three-dimensional packing of (I)

viewed down the b axis.

4. Synthesis and crystallization

The title compound was obtained under hydrothermal conditions from a mixture of iron(II) sulfate heptahydrate (28 mg, 0.1 mmol), 2-(pyridin-2-yl)-1H-imidazole (15 mg, 0.1 mmol) and potassium tricyanomethanide KC(CN)₃ (26 mg, 0.2 mmol) in water-ethanol (4:1 v/v, 20 ml). The mixture was transferred to a Teflon-lined autoclave and heated at 423 K for 48 h. The autoclave was then allowed to cool to ambient temperature. Block-like yellow crystals of (I) were collected by filtration, washed with water and dried in air (yield 58%).

5. Refinement details

Crystal data, data collection and structure refinement details are summarized in Table 2. H atoms bonded to C atoms were placed at geometrically calculated positions and refined using a riding model. C—H distances were fixed to 0.93 Å for aromatic C atoms, with U_iso(H) = 1.2U_eq(C). The H atoms attached to O and N atoms were located in a difference Fourier map and were refined isotropically.

Table 2
Experimental details

Crystal data
Chemical formula	[Fe(C₈H₇N₃)(H₂O)₄]SO₄
M_r	369.14
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	293
a, b, c (Å)	12.476 (5), 11.741 (5), 20.313 (7)
V (Å³)	2975.5 (19)
Z	8
Radiation type	Mo Kα
μ (mm⁻¹)	1.19
Crystal size (mm)	0.34 × 0.20 × 0.11

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2009 )
T_min, T_max	0.802, 0.871
No. of measured, independent and observed [I > 2σ(I)] reflections	20168, 4417, 3008
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.715

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.091, 1.08
No. of reflections	4417
No. of parameters	226
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.47, −0.41
Computer programs: APEX2 and SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008 ), SHELXL2014 (Sheldrick, 2015 ), ORTEP-3 for Windows and WinGX(Farrugia, 2012 ), Mercury (Macrae, 2006 ) and PARST (Nardelli, 1995 ).

Supporting information

CCDC reference: 1051905

Crystal structure: contains datablocks global, I. DOI: 10.1107/S2056989015004417/wm5132sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989015004417/wm5132Isup2.hkl

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: APEX2 and SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae, 2006); software used to prepare material for publication: WinGX (Farrugia, 2012) and PARST (Nardelli, 1995).

Tetraaqua[2-(pyridin-2-yl)-1H-imidazole-κ²N²,N³]iron(II) sulfate top

Crystal data top

[Fe(C₈H₇N₃)(H₂O)₄]SO₄	F(000) = 1520
M_r = 369.14	D_x = 1.648 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 9606 reflections
a = 12.476 (5) Å	θ = 2.5–30.0°
b = 11.741 (5) Å	µ = 1.19 mm⁻¹
c = 20.313 (7) Å	T = 293 K
V = 2975.5 (19) Å³	Block, yellow
Z = 8	0.34 × 0.20 × 0.11 mm

Data collection top

Bruker APEXII CCD diffractometer	4417 independent reflections
Radiation source: fine-focus sealed tube	3008 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
φ & ω scans	θ_max = 30.5°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −17→17
T_min = 0.802, T_max = 0.871	k = −14→16
20168 measured reflections	l = −28→27

Refinement top

Refinement on F²	226 parameters
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.036	w = 1/[σ²(F_o²) + (0.041P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.091	(Δ/σ)_max < 0.001
S = 1.08	Δρ_max = 0.47 e Å⁻³
4417 reflections	Δρ_min = −0.41 e Å⁻³

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.

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

	x	y	z	U_iso*/U_eq
Fe1	0.45016 (2)	0.72203 (3)	0.35060 (2)	0.02305 (9)
S1	0.74974 (4)	0.47721 (5)	0.30259 (2)	0.02198 (11)
O1	0.69197 (10)	0.52744 (13)	0.24568 (6)	0.0295 (3)
O2	0.69268 (12)	0.50603 (15)	0.36361 (7)	0.0378 (4)
O3	0.85850 (11)	0.52416 (15)	0.30581 (7)	0.0368 (4)
O4	0.75368 (13)	0.35340 (15)	0.29605 (7)	0.0441 (4)
O5	0.45617 (15)	0.89924 (16)	0.33077 (10)	0.0416 (4)
O6	0.50247 (15)	0.66267 (16)	0.25674 (7)	0.0336 (4)
O7	0.29469 (14)	0.71843 (19)	0.30864 (8)	0.0322 (4)
O8	0.61694 (12)	0.72412 (17)	0.37388 (8)	0.0314 (4)
N1	0.42117 (13)	0.54515 (16)	0.38829 (7)	0.0274 (4)
N2	0.40687 (14)	0.74690 (16)	0.45132 (8)	0.0294 (4)
N3	0.35709 (14)	0.6734 (2)	0.54639 (8)	0.0353 (5)
C1	0.42985 (17)	0.4458 (2)	0.35520 (10)	0.0357 (5)
H1	0.4548	0.4477	0.3121	0.043*
C2	0.40365 (18)	0.3420 (2)	0.38200 (11)	0.0405 (6)
H2	0.4107	0.2753	0.3577	0.049*
C3	0.36666 (19)	0.3396 (2)	0.44581 (12)	0.0438 (6)
H3	0.3484	0.2707	0.4654	0.053*
C4	0.35690 (17)	0.4400 (2)	0.48053 (11)	0.0387 (6)
H4	0.3314	0.4397	0.5235	0.046*
C5	0.38537 (15)	0.5406 (2)	0.45065 (9)	0.0279 (5)
C6	0.38177 (14)	0.6510 (2)	0.48286 (9)	0.0283 (5)
C7	0.36954 (17)	0.7871 (2)	0.55631 (11)	0.0398 (6)
H7	0.3593	0.8266	0.5955	0.048*
C8	0.40013 (17)	0.8319 (2)	0.49715 (10)	0.0362 (5)
H8	0.4142	0.9085	0.4893	0.043*
H1O5	0.510 (2)	0.932 (2)	0.3248 (13)	0.049 (8)*
H2O5	0.408 (3)	0.933 (3)	0.3090 (15)	0.084 (12)*
H1O6	0.5519 (19)	0.632 (2)	0.2580 (12)	0.036 (8)*
H2O6	0.453 (2)	0.617 (3)	0.2387 (13)	0.062 (9)*
H1O7	0.273 (2)	0.672 (3)	0.2986 (13)	0.045 (11)*
H2O7	0.286 (2)	0.770 (3)	0.2761 (16)	0.066 (10)*
H1O8	0.652 (2)	0.760 (2)	0.3515 (11)	0.038 (8)*
H2O8	0.644 (2)	0.658 (3)	0.3708 (13)	0.050 (9)*
H3N	0.3399 (19)	0.615 (2)	0.5753 (13)	0.054 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe1	0.02282 (15)	0.02469 (18)	0.02163 (14)	−0.00077 (12)	0.00178 (10)	0.00238 (11)
S1	0.0206 (2)	0.0222 (3)	0.0231 (2)	0.00159 (19)	−0.00054 (17)	0.00183 (18)
O1	0.0279 (7)	0.0296 (9)	0.0309 (7)	0.0009 (6)	−0.0064 (5)	0.0067 (6)
O2	0.0427 (9)	0.0408 (11)	0.0300 (7)	0.0072 (8)	0.0144 (6)	0.0084 (7)
O3	0.0214 (7)	0.0493 (12)	0.0397 (8)	−0.0045 (7)	−0.0021 (6)	0.0095 (7)
O4	0.0598 (10)	0.0226 (10)	0.0500 (9)	0.0088 (8)	−0.0224 (8)	−0.0042 (7)
O5	0.0300 (9)	0.0299 (11)	0.0649 (11)	−0.0052 (8)	−0.0073 (8)	0.0177 (8)
O6	0.0263 (8)	0.0449 (12)	0.0296 (8)	0.0023 (9)	0.0008 (6)	−0.0053 (7)
O7	0.0292 (8)	0.0304 (11)	0.0370 (9)	−0.0006 (8)	−0.0061 (6)	−0.0014 (8)
O8	0.0250 (8)	0.0322 (11)	0.0372 (8)	−0.0020 (8)	−0.0001 (6)	0.0057 (8)
N1	0.0290 (9)	0.0306 (11)	0.0226 (8)	−0.0024 (8)	−0.0005 (6)	0.0035 (7)
N2	0.0272 (9)	0.0343 (12)	0.0267 (9)	0.0011 (8)	0.0019 (7)	−0.0027 (7)
N3	0.0344 (10)	0.0474 (14)	0.0241 (9)	−0.0006 (9)	0.0072 (7)	0.0031 (8)
C1	0.0399 (12)	0.0366 (15)	0.0305 (11)	0.0023 (11)	−0.0040 (9)	−0.0014 (9)
C2	0.0422 (13)	0.0323 (15)	0.0470 (13)	−0.0037 (12)	−0.0076 (10)	−0.0068 (11)
C3	0.0430 (14)	0.0397 (17)	0.0486 (14)	−0.0108 (12)	−0.0005 (10)	0.0068 (11)
C4	0.0341 (12)	0.0483 (17)	0.0338 (11)	−0.0112 (11)	0.0032 (9)	0.0090 (10)
C5	0.0209 (9)	0.0370 (14)	0.0257 (9)	−0.0040 (9)	−0.0015 (7)	0.0048 (8)
C6	0.0211 (9)	0.0413 (15)	0.0227 (9)	−0.0017 (9)	0.0033 (7)	0.0050 (8)
C7	0.0352 (12)	0.0516 (18)	0.0326 (11)	0.0047 (11)	0.0045 (9)	−0.0049 (10)
C8	0.0353 (12)	0.0340 (15)	0.0395 (12)	0.0010 (11)	0.0022 (9)	−0.0073 (10)

Geometric parameters (Å, º) top

Fe1—O7	2.1191 (18)	N1—C1	1.351 (3)
Fe1—O5	2.121 (2)	N2—C6	1.333 (3)
Fe1—O6	2.1323 (15)	N2—C8	1.368 (3)
Fe1—O8	2.1340 (17)	N3—C6	1.353 (2)
Fe1—N2	2.1361 (17)	N3—C7	1.359 (3)
Fe1—N1	2.243 (2)	N3—H3N	0.93 (3)
S1—O4	1.4605 (19)	C1—C2	1.373 (4)
S1—O3	1.4661 (16)	C1—H1	0.9300
S1—O2	1.4688 (14)	C2—C3	1.376 (3)
S1—O1	1.4844 (14)	C2—H2	0.9300
O5—H1O5	0.78 (3)	C3—C4	1.379 (4)
O5—H2O5	0.85 (3)	C3—H3	0.9300
O6—H1O6	0.71 (2)	C4—C5	1.374 (3)
O6—H2O6	0.89 (3)	C4—H4	0.9300
O7—H1O7	0.64 (3)	C5—C6	1.453 (3)
O7—H2O7	0.90 (3)	C7—C8	1.366 (3)
O8—H1O8	0.76 (3)	C7—H7	0.9300
O8—H2O8	0.84 (3)	C8—H8	0.9300
N1—C5	1.344 (2)

O7—Fe1—O5	88.60 (8)	C5—N1—C1	117.44 (19)
O7—Fe1—O6	85.07 (7)	C5—N1—Fe1	114.36 (15)
O5—Fe1—O6	98.06 (8)	C1—N1—Fe1	128.10 (14)
O7—Fe1—O8	169.08 (6)	C6—N2—C8	105.96 (18)
O5—Fe1—O8	89.79 (7)	C6—N2—Fe1	113.84 (14)
O6—Fe1—O8	84.46 (7)	C8—N2—Fe1	140.12 (17)
O7—Fe1—N2	99.00 (7)	C6—N3—C7	107.85 (19)
O5—Fe1—N2	93.25 (8)	C6—N3—H3N	120.6 (17)
O6—Fe1—N2	168.09 (7)	C7—N3—H3N	131.4 (17)
O8—Fe1—N2	91.87 (7)	N1—C1—C2	123.3 (2)
O7—Fe1—N1	88.35 (7)	N1—C1—H1	118.3
O5—Fe1—N1	168.26 (7)	C2—C1—H1	118.3
O6—Fe1—N1	92.97 (7)	C1—C2—C3	118.2 (2)
O8—Fe1—N1	95.29 (7)	C1—C2—H2	120.9
N2—Fe1—N1	76.04 (7)	C3—C2—H2	120.9
O4—S1—O3	110.31 (10)	C2—C3—C4	119.5 (2)
O4—S1—O2	108.80 (10)	C2—C3—H3	120.2
O3—S1—O2	108.93 (9)	C4—C3—H3	120.2
O4—S1—O1	109.93 (9)	C5—C4—C3	119.1 (2)
O3—S1—O1	109.55 (9)	C5—C4—H4	120.5
O2—S1—O1	109.29 (9)	C3—C4—H4	120.5
Fe1—O5—H1O5	123 (2)	N1—C5—C4	122.4 (2)
Fe1—O5—H2O5	122 (2)	N1—C5—C6	113.50 (18)
H1O5—O5—H2O5	108 (3)	C4—C5—C6	124.04 (19)
Fe1—O6—H1O6	113.3 (19)	N2—C6—N3	110.3 (2)
Fe1—O6—H2O6	110.5 (17)	N2—C6—C5	122.02 (17)
H1O6—O6—H2O6	108 (3)	N3—C6—C5	127.6 (2)
Fe1—O7—H1O7	122 (3)	N3—C7—C8	106.2 (2)
Fe1—O7—H2O7	113.1 (18)	N3—C7—H7	126.9
H1O7—O7—H2O7	106 (3)	C8—C7—H7	126.9
Fe1—O8—H1O8	115.5 (19)	C7—C8—N2	109.6 (2)
Fe1—O8—H2O8	111.1 (18)	C7—C8—H8	125.2
H1O8—O8—H2O8	104 (3)	N2—C8—H8	125.2

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H1O5···O3ⁱ	0.78 (3)	2.00 (3)	2.785 (3)	175 (3)
O5—H2O5···O1ⁱⁱ	0.85 (4)	2.00 (3)	2.845 (3)	172 (4)
O6—H1O6···O1	0.71 (3)	2.15 (3)	2.857 (3)	170 (3)
O6—H2O6···O3ⁱⁱⁱ	0.89 (3)	1.85 (3)	2.736 (3)	175 (3)
O7—H1O7···O1ⁱⁱⁱ	0.64 (4)	2.17 (3)	2.809 (3)	173 (4)
O7—H2O7···O4ⁱⁱ	0.90 (4)	1.83 (3)	2.720 (3)	168 (4)
O8—H1O8···O4ⁱ	0.76 (3)	1.96 (3)	2.722 (3)	178 (4)
O8—H2O8···O2	0.84 (3)	1.90 (3)	2.737 (3)	175 (3)
N3—H3N···O2^iv	0.93 (3)	1.93 (3)	2.858 (3)	178 (3)
C4—H4···O2^iv	0.93	2.40	3.287 (3)	160

Symmetry codes: (i) −x+3/2, y+1/2, z; (ii) −x+1, y+1/2, −z+1/2; (iii) x−1/2, y, −z+1/2; (iv) −x+1, −y+1, −z+1.

Acknowledgements

SZ, SF and MH acknowledge the Algerian Ministry of Higher Education and Scientific Research, the Algerian Directorate General for Scientific Research and Technological Development and Ferhat Abbas Sétif 1 University for financial support. BMF and SBN thank the Ministry of Education and Science of the Republic of Serbia for financial support (project Nos. 172014 and 172035).

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