fac-Bis[bis­(pyridin-2-yl)methanamine]­iron(II) bis­(1,1,3,3-tetra­cyano-2-eth­oxy­propenide) dihydrate

Setifi, Z.; Bernès, S.; Setifi, F.; Kaur, M.; Jasinski, J.P.

doi:10.1107/S2414314617010070

metal-organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 2| Part 7| July 2017| x171007

https://doi.org/10.1107/S2414314617010070

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fac-Bis[bis(pyridin-2-yl)methanamine]iron(II) bis(1,1,3,3-tetracyano-2-ethoxypropenide) dihydrate

Zouaoui Setifi,^a,^b Sylvain Bernès,^c ^* Fatima Setifi,^b ^* Manpreet Kaur ^d and Jerry P. Jasinski ^d

^aDépartement de Technologie, Faculté de Technologie, Université 20 Août 1955-Skikda, BP 26, Route d'El-Hadaiek, Skikda 21000, Algeria, ^bLaboratoire de Chimie, Ingénierie Moléculaire et Nanostructures (LCIMN), Université Ferhat Abbas Sétif 1, Sétif 19000, Algeria, ^cInstituto de Física, Benemérita Universidad Autónoma de Puebla, Av. San Claudio y 18 Sur, 72570 Puebla, Pue., Mexico, and ^dDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435, USA
^*Correspondence e-mail: sylvain_bernes@hotmail.com, fat_setifi@yahoo.fr

Edited by M. Weil, Vienna University of Technology, Austria (Received 27 June 2017; accepted 6 July 2017; online 18 July 2017)

The hydrated complex [Fe(DIPA)₂](tcnoet)₂·2H₂O [DIPA is bis(pyridin-2-yl)methanamine, C₁₁H₁₁N₃, and tcnoet is the anion 1,1,3,3-tetracyano-2-ethoxypropenide, C₉H₅N₄O⁻], crystallizes with the [Fe(DIPA)₂]²⁺ cation located on an inversion centre. The coordination geometry for Fe^II is strongly distorted from octahedral, as a consequence of the bite angles formed by the tridentate DIPA ligand. The water molecules included in the voids left by the cations and anions form hydrogen bonds with the cyano and amine groups.

Keywords: crystal structure; iron; amine ligand; hydrogen bond.

CCDC reference: 1560707

Structure description

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 (Yuste et al., 2009 ; Atmani et al., 2008 ; Benmansour et al., 2008 , 2012 ; Miyazaki et al., 2003 ; Setifi, Domasevitch et al., 2013 ; Setifi, Charles et al., 2013 ; Setifi, Milin et al., 2014 ; Setifi, Lehchili et al., 2014 ; Setifi, Setifi et al., 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 phenomenon. In an attempt to prepare such an iron(II) complex using hydrothermal synthesis, we obtained instead the title compound.

In the title compound, the complex cation lies on an inversion centre, while the organic anion and the lattice water molecule are in general positions, giving the chemical formula [Fe(DIPA)₂](tcnoet)₂·2H₂O, where DIPA is the tridentate amine ligand bis(pyridin-2-yl)methanamine and tcnoet is the anion 1,1,3,3-tetracyano-2-ethoxypropenide (Fig. 1). The triamine ligand displays a butterfly conformation, imposed by the sp³ hybridization of the central C atom C6, giving a dihedral angle between the pyridyl rings of 75.87 (8)°. The three N donors coordinate in a facial arrangement, with very similar Fe—N bond lengths [range: 1.9904 (18)–2.0106 (19) Å]. However, the octahedral coordination geometry for the metal is strongly distorted as a consequence of the steric strain originating from the bite angles formed by the ligand in the five-membered metalacycles: N1—Fe1—N2 = 80.28 (8)° and N2—Fe1—N3 = 80.95 (8)°. Such a distortion has been observed in other octahedral complexes featuring this ligand with different transition metals (Fe^II, Co^III, Ni^II, Cu^II: Bernhardt et al., 1992 ; Fe^III: Renz et al., 1999 ; Mn^II: Bräuer et al., 2011 ). Regarding the free anion tcnoet, its twisted conformation, characterized by a dihedral angle of 29.8 (2)° between the dicyano C(CN)₂ mean planes, is not uncommon, and is indeed comparable to that observed in the 2,2′-bipyridin-1-ium salt (Setifi et al., 2015 ; dihedral angle: 22.4°).

Figure 1
The structures of the molecular components in the title compound, with displacement ellipsoids drawn at the 30% probability level. Non-labelled atoms in the cation are generated by the symmetry operation 1 − x, 1 − y, 1 − z.

The water molecule behaves both as donor and acceptor for hydrogen bonding, stabilizing the crystal structure with three weak hydrogen bonds involving two symmetry-related tcnoet anions and the central amine group of the DIPA ligand (Table 1 and Fig. 2).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N15ⁱ	0.86 (4)	2.12 (4)	2.976 (3)	172 (3)
O1—H2⋯N17	0.84 (4)	2.09 (4)	2.921 (3)	175 (4)
N2—H2B⋯O1ⁱⁱ	0.91	2.25	3.065 (3)	149
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) -x+1, -y+2, -z+1.

Figure 2
Part of the crystal structure, showing the hydrogen bonds formed by the water molecule (dashed lines). [Symmetry codes: i 1 − x, 2 − y, 1 − z; ii 1 − x, $[{1\over 2}]$ + y, $[{3\over 2}]$ − z.]

Synthesis and crystallization

The salt K(tcnoet) was prepared using the published method (Middleton et al., 1958 ). The title compound was synthesized hydrothermally under autogenous pressure from a mixture of FeSO₄·7H₂O (28 mg, 0.1 mmol), DIPA (19 mg, 0.1 mmol) and K(tcnoet) (45 mg, 0.2 mmol) in water–methanol (4:1 v/v, 20 cm³). This mixture was sealed in a Teflon-lined autoclave and held at 423 K for 3 days, and then cooled to ambient temperature at a rate of 10 K h⁻¹ (yield: 23%). Red prisms of the title compound suitable for single-crystal X-ray diffraction were selected directly from the synthesized product.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. Two reflections ( $[\overline{1}]$ 9 1, $[\overline{2}]$ 9 1) were omitted because of poor agreement between calculated and observed intensities.

Table 2
Experimental details

Crystal data
Chemical formula	[Fe(C₁₁H₁₁N₃)₂](C₉H₅N₄O)₂·2H₂O
M_r	832.68
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	11.8904 (3), 7.5824 (3), 22.5912 (7)
β (°)	102.648 (3)
V (Å³)	1987.35 (11)
Z	2
Radiation type	Cu Kα
μ (mm⁻¹)	3.55
Crystal size (mm)	0.12 × 0.08 × 0.07

Data collection
Diffractometer	Agilent Xcalibur
Absorption correction	Multi-scan (CrysAlis PRO; Rigaku OD, 2015 )
T_min, T_max	0.843, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	8154, 3799, 3393
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.615

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.115, 1.07
No. of reflections	3799
No. of parameters	275
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.32
Computer programs: CrysAlis PRO (Rigaku OD, 2015), SHELXT2014 (Sheldrick, 2015a ), SHELXL2016 (Sheldrick, 2015b ), XP in SHELXTL-Plus (Sheldrick, 2008 ) and Mercury (Macrae et al., 2008 ).

Structural data

CCDC reference: 1560707

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S2414314617010070/wm4052sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617010070/wm4052Isup2.hkl

checkCIF report

Computing details top

Data collection: CrysAlis PRO (Rigaku OD, 2015); cell refinement: CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015b); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 2008) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2016 (Sheldrick, 2015b).

fac-Bis[bis(pyridin-2-yl)methanamine]iron(II) bis(1,1,3,3-tetracyano-2-ethoxypropenide) dihydrate top

Crystal data top

[Fe(C₁₁H₁₁N₃)₂](C₉H₅N₄O)₂·2H₂O	F(000) = 864
M_r = 832.68	D_x = 1.391 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54184 Å
a = 11.8904 (3) Å	Cell parameters from 3092 reflections
b = 7.5824 (3) Å	θ = 4.9–71.4°
c = 22.5912 (7) Å	µ = 3.55 mm⁻¹
β = 102.648 (3)°	T = 173 K
V = 1987.35 (11) Å³	Prism, red
Z = 2	0.12 × 0.08 × 0.07 mm

Data collection top

Agilent Xcalibur diffractometer	3799 independent reflections
Radiation source: Enhance (Cu) X-ray Source	3393 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
Detector resolution: 16.0416 pixels mm^-1	θ_max = 71.5°, θ_min = 3.8°
ω scans	h = −8→14
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015)	k = −9→9
T_min = 0.843, T_max = 1.000	l = −27→26
8154 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)] = 0.045	Hydrogen site location: mixed
wR(F²) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ²(F_o²) + (0.0542P)² + 1.1004P] where P = (F_o² + 2F_c²)/3
3799 reflections	(Δ/σ)_max < 0.001
275 parameters	Δρ_max = 0.45 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³
0 constraints

Special details top

Refinement. H atoms for the water molecule, H1 and H2, were found in a difference map and refined freely, while other H atoms were placed in calculated positions.

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

	x	y	z	U_iso*/U_eq
Fe1	0.500000	0.500000	0.500000	0.02633 (14)
N1	0.47707 (16)	0.5225 (2)	0.41019 (8)	0.0283 (4)
N2	0.58098 (16)	0.7306 (3)	0.49521 (8)	0.0303 (4)
H2B	0.530419	0.819642	0.481911	0.036*
H2C	0.627271	0.760881	0.531435	0.036*
N3	0.65696 (15)	0.4086 (3)	0.50006 (8)	0.0287 (4)
C1	0.3948 (2)	0.4541 (3)	0.36576 (11)	0.0349 (5)
H1A	0.334845	0.386283	0.376208	0.042*
C2	0.3951 (2)	0.4799 (4)	0.30524 (11)	0.0428 (6)
H2A	0.336248	0.429819	0.274536	0.051*
C3	0.4821 (2)	0.5793 (4)	0.28976 (11)	0.0448 (6)
H3A	0.484164	0.597059	0.248387	0.054*
C4	0.5656 (2)	0.6523 (4)	0.33527 (11)	0.0381 (5)
H4A	0.625319	0.722921	0.325822	0.046*
C5	0.56069 (18)	0.6207 (3)	0.39475 (10)	0.0300 (5)
C6	0.64886 (19)	0.6820 (3)	0.44945 (10)	0.0317 (5)
H6A	0.697765	0.781002	0.440069	0.038*
C7	0.71790 (19)	0.5212 (3)	0.47388 (10)	0.0305 (5)
C8	0.82888 (19)	0.4864 (3)	0.46739 (11)	0.0339 (5)
H8A	0.869537	0.569249	0.448410	0.041*
C9	0.8789 (2)	0.3285 (4)	0.48920 (11)	0.0374 (5)
H9A	0.955088	0.300655	0.485800	0.045*
C10	0.8163 (2)	0.2115 (4)	0.51606 (11)	0.0389 (5)
H10A	0.848966	0.101461	0.530923	0.047*
C11	0.7063 (2)	0.2551 (3)	0.52122 (10)	0.0344 (5)
H11A	0.664212	0.174451	0.540237	0.041*
C12	0.09125 (19)	0.7045 (3)	0.67459 (10)	0.0304 (5)
C13	0.21113 (19)	0.6807 (3)	0.69238 (10)	0.0337 (5)
C14	0.2614 (2)	0.5841 (4)	0.74535 (11)	0.0397 (6)
N15	0.3030 (2)	0.5080 (4)	0.78845 (11)	0.0539 (7)
C16	0.28834 (19)	0.7605 (3)	0.66036 (10)	0.0343 (5)
N17	0.35231 (17)	0.8214 (3)	0.63518 (10)	0.0431 (5)
C18	0.03496 (19)	0.8350 (3)	0.63568 (10)	0.0319 (5)
C19	−0.0856 (2)	0.8176 (3)	0.61052 (11)	0.0359 (5)
N20	−0.18179 (19)	0.8052 (3)	0.58885 (11)	0.0495 (6)
C21	0.0890 (2)	0.9891 (3)	0.61936 (13)	0.0406 (6)
N22	0.1294 (2)	1.1153 (4)	0.60585 (15)	0.0630 (8)
O23	0.01861 (14)	0.5995 (2)	0.69608 (8)	0.0359 (4)
C24	0.0371 (2)	0.4105 (4)	0.70181 (12)	0.0420 (6)
H24A	0.066260	0.377862	0.744869	0.050*
H24B	0.093996	0.372397	0.678350	0.050*
C25	−0.0772 (3)	0.3253 (4)	0.67742 (14)	0.0521 (7)
H25A	−0.069029	0.196912	0.681080	0.078*
H25B	−0.104317	0.357179	0.634632	0.078*
H25C	−0.132936	0.365979	0.700568	0.078*
O1	0.54085 (17)	0.9789 (3)	0.58946 (8)	0.0392 (4)
H1	0.591 (3)	0.990 (4)	0.6229 (18)	0.059*
H2	0.487 (3)	0.928 (5)	0.6009 (16)	0.059*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe1	0.0235 (2)	0.0339 (3)	0.0221 (2)	−0.0020 (2)	0.00606 (17)	−0.0021 (2)
N1	0.0273 (9)	0.0310 (10)	0.0267 (9)	0.0039 (7)	0.0060 (7)	0.0008 (7)
N2	0.0303 (9)	0.0317 (10)	0.0284 (9)	−0.0034 (8)	0.0053 (7)	−0.0018 (8)
N3	0.0269 (8)	0.0354 (10)	0.0237 (8)	−0.0022 (8)	0.0051 (7)	−0.0026 (8)
C1	0.0321 (11)	0.0411 (13)	0.0302 (11)	0.0022 (10)	0.0040 (9)	−0.0021 (10)
C2	0.0405 (13)	0.0561 (17)	0.0284 (12)	0.0081 (12)	0.0005 (10)	−0.0026 (11)
C3	0.0489 (14)	0.0619 (18)	0.0246 (11)	0.0167 (13)	0.0101 (10)	0.0075 (11)
C4	0.0367 (12)	0.0447 (14)	0.0349 (12)	0.0072 (11)	0.0118 (10)	0.0113 (11)
C5	0.0308 (10)	0.0299 (11)	0.0305 (11)	0.0066 (9)	0.0096 (9)	0.0051 (9)
C6	0.0316 (10)	0.0313 (12)	0.0333 (11)	−0.0043 (9)	0.0098 (9)	0.0015 (9)
C7	0.0294 (11)	0.0352 (12)	0.0261 (10)	−0.0040 (9)	0.0041 (9)	0.0004 (9)
C8	0.0277 (11)	0.0425 (14)	0.0309 (11)	−0.0053 (10)	0.0050 (9)	−0.0002 (10)
C9	0.0280 (10)	0.0495 (15)	0.0331 (12)	0.0044 (10)	0.0035 (9)	−0.0044 (11)
C10	0.0408 (12)	0.0390 (13)	0.0334 (12)	0.0058 (11)	0.0004 (10)	0.0033 (10)
C11	0.0390 (12)	0.0353 (13)	0.0282 (10)	−0.0003 (10)	0.0058 (9)	0.0045 (10)
C12	0.0309 (10)	0.0350 (12)	0.0272 (10)	−0.0021 (9)	0.0101 (9)	−0.0021 (9)
C13	0.0310 (11)	0.0423 (14)	0.0287 (11)	0.0007 (10)	0.0085 (9)	0.0036 (10)
C14	0.0297 (11)	0.0538 (16)	0.0372 (13)	0.0040 (11)	0.0109 (10)	0.0052 (12)
N15	0.0409 (12)	0.0785 (19)	0.0416 (13)	0.0115 (12)	0.0074 (10)	0.0193 (13)
C16	0.0280 (10)	0.0444 (14)	0.0284 (11)	−0.0005 (10)	0.0013 (9)	−0.0008 (10)
N17	0.0291 (9)	0.0625 (15)	0.0378 (11)	−0.0054 (10)	0.0074 (9)	0.0055 (10)
C18	0.0286 (10)	0.0354 (13)	0.0329 (11)	−0.0019 (9)	0.0093 (9)	0.0031 (10)
C19	0.0368 (13)	0.0357 (13)	0.0354 (12)	0.0031 (10)	0.0084 (10)	0.0055 (10)
N20	0.0375 (12)	0.0540 (15)	0.0526 (13)	−0.0038 (10)	0.0006 (10)	0.0110 (12)
C21	0.0349 (12)	0.0391 (14)	0.0515 (15)	0.0061 (11)	0.0174 (11)	0.0070 (12)
N22	0.0562 (14)	0.0428 (14)	0.102 (2)	0.0016 (12)	0.0435 (15)	0.0168 (15)
O23	0.0346 (8)	0.0367 (9)	0.0398 (9)	0.0000 (7)	0.0156 (7)	0.0070 (7)
C24	0.0467 (14)	0.0387 (14)	0.0432 (14)	−0.0013 (11)	0.0156 (11)	0.0057 (11)
C25	0.0606 (17)	0.0489 (17)	0.0465 (15)	−0.0134 (14)	0.0112 (13)	−0.0009 (13)
O1	0.0429 (10)	0.0412 (10)	0.0338 (9)	−0.0055 (8)	0.0094 (8)	0.0029 (8)

Geometric parameters (Å, º) top

Fe1—N3ⁱ	1.9904 (18)	C8—H8A	0.9500
Fe1—N3	1.9904 (18)	C9—C10	1.380 (4)
Fe1—N1ⁱ	1.9944 (18)	C9—H9A	0.9500
Fe1—N1	1.9944 (18)	C10—C11	1.379 (3)
Fe1—N2ⁱ	2.0106 (19)	C10—H10A	0.9500
Fe1—N2	2.0106 (19)	C11—H11A	0.9500
N1—C1	1.343 (3)	C12—O23	1.341 (3)
N1—C5	1.348 (3)	C12—C18	1.393 (3)
N2—C6	1.490 (3)	C12—C13	1.405 (3)
N2—H2B	0.9100	C13—C14	1.418 (3)
N2—H2C	0.9100	C13—C16	1.423 (3)
N3—C7	1.338 (3)	C14—N15	1.147 (3)
N3—C11	1.343 (3)	C16—N17	1.142 (3)
C1—C2	1.382 (3)	C18—C21	1.420 (3)
C1—H1A	0.9500	C18—C19	1.428 (3)
C2—C3	1.385 (4)	C19—N20	1.145 (3)
C2—H2A	0.9500	C21—N22	1.142 (4)
C3—C4	1.379 (4)	O23—C24	1.451 (3)
C3—H3A	0.9500	C24—C25	1.496 (4)
C4—C5	1.379 (3)	C24—H24A	0.9900
C4—H4A	0.9500	C24—H24B	0.9900
C5—C6	1.508 (3)	C25—H25A	0.9800
C6—C7	1.506 (3)	C25—H25B	0.9800
C6—H6A	1.0000	C25—H25C	0.9800
C7—C8	1.385 (3)	O1—H1	0.86 (4)
C8—C9	1.379 (4)	O1—H2	0.84 (4)

N3ⁱ—Fe1—N3	180.0	N2—C6—H6A	112.9
N3ⁱ—Fe1—N1ⁱ	87.13 (7)	C7—C6—H6A	112.9
N3—Fe1—N1ⁱ	92.87 (7)	C5—C6—H6A	112.9
N3ⁱ—Fe1—N1	92.88 (7)	N3—C7—C8	123.1 (2)
N3—Fe1—N1	87.13 (7)	N3—C7—C6	111.96 (19)
N1ⁱ—Fe1—N1	180.0	C8—C7—C6	124.8 (2)
N3ⁱ—Fe1—N2ⁱ	80.95 (8)	C9—C8—C7	118.3 (2)
N3—Fe1—N2ⁱ	99.05 (8)	C9—C8—H8A	120.9
N1ⁱ—Fe1—N2ⁱ	80.28 (8)	C7—C8—H8A	120.9
N1—Fe1—N2ⁱ	99.72 (8)	C8—C9—C10	118.9 (2)
N3ⁱ—Fe1—N2	99.05 (8)	C8—C9—H9A	120.5
N3—Fe1—N2	80.95 (8)	C10—C9—H9A	120.5
N1ⁱ—Fe1—N2	99.72 (8)	C11—C10—C9	119.7 (2)
N1—Fe1—N2	80.27 (8)	C11—C10—H10A	120.1
N2ⁱ—Fe1—N2	180.0	C9—C10—H10A	120.1
C1—N1—C5	118.5 (2)	N3—C11—C10	121.7 (2)
C1—N1—Fe1	129.96 (16)	N3—C11—H11A	119.1
C5—N1—Fe1	111.50 (15)	C10—C11—H11A	119.1
C6—N2—Fe1	99.26 (13)	O23—C12—C18	113.05 (19)
C6—N2—H2B	111.9	O23—C12—C13	120.9 (2)
Fe1—N2—H2B	111.9	C18—C12—C13	126.1 (2)
C6—N2—H2C	111.9	C12—C13—C14	121.4 (2)
Fe1—N2—H2C	111.9	C12—C13—C16	121.8 (2)
H2B—N2—H2C	109.6	C14—C13—C16	116.7 (2)
C7—N3—C11	118.26 (19)	N15—C14—C13	179.0 (3)
C7—N3—Fe1	112.10 (16)	N17—C16—C13	178.3 (3)
C11—N3—Fe1	129.63 (16)	C12—C18—C21	124.5 (2)
N1—C1—C2	121.7 (2)	C12—C18—C19	119.2 (2)
N1—C1—H1A	119.1	C21—C18—C19	116.4 (2)
C2—C1—H1A	119.1	N20—C19—C18	178.1 (3)
C1—C2—C3	119.4 (2)	N22—C21—C18	178.0 (3)
C1—C2—H2A	120.3	C12—O23—C24	121.45 (18)
C3—C2—H2A	120.3	O23—C24—C25	106.6 (2)
C4—C3—C2	119.1 (2)	O23—C24—H24A	110.4
C4—C3—H3A	120.5	C25—C24—H24A	110.4
C2—C3—H3A	120.5	O23—C24—H24B	110.4
C5—C4—C3	118.6 (2)	C25—C24—H24B	110.4
C5—C4—H4A	120.7	H24A—C24—H24B	108.6
C3—C4—H4A	120.7	C24—C25—H25A	109.5
N1—C5—C4	122.7 (2)	C24—C25—H25B	109.5
N1—C5—C6	112.21 (19)	H25A—C25—H25B	109.5
C4—C5—C6	125.1 (2)	C24—C25—H25C	109.5
N2—C6—C7	106.29 (18)	H25A—C25—H25C	109.5
N2—C6—C5	105.05 (17)	H25B—C25—H25C	109.5
C7—C6—C5	106.01 (19)	H1—O1—H2	102 (3)

C5—N1—C1—C2	1.0 (3)	C5—C6—C7—N3	−71.4 (2)
Fe1—N1—C1—C2	−177.85 (19)	N2—C6—C7—C8	−143.5 (2)
N1—C1—C2—C3	−0.3 (4)	C5—C6—C7—C8	105.0 (2)
C1—C2—C3—C4	−0.8 (4)	N3—C7—C8—C9	−0.2 (4)
C2—C3—C4—C5	1.2 (4)	C6—C7—C8—C9	−176.3 (2)
C1—N1—C5—C4	−0.6 (3)	C7—C8—C9—C10	0.5 (3)
Fe1—N1—C5—C4	178.47 (18)	C8—C9—C10—C11	−0.7 (4)
C1—N1—C5—C6	−177.8 (2)	C7—N3—C11—C10	−0.5 (3)
Fe1—N1—C5—C6	1.2 (2)	Fe1—N3—C11—C10	178.39 (17)
C3—C4—C5—N1	−0.5 (4)	C9—C10—C11—N3	0.8 (4)
C3—C4—C5—C6	176.3 (2)	O23—C12—C13—C14	−18.8 (4)
Fe1—N2—C6—C7	−55.23 (17)	C18—C12—C13—C14	159.7 (3)
Fe1—N2—C6—C5	56.87 (17)	O23—C12—C13—C16	165.0 (2)
N1—C5—C6—N2	−40.1 (2)	C18—C12—C13—C16	−16.5 (4)
C4—C5—C6—N2	142.7 (2)	O23—C12—C18—C21	162.7 (2)
N1—C5—C6—C7	72.2 (2)	C13—C12—C18—C21	−15.9 (4)
C4—C5—C6—C7	−105.0 (3)	O23—C12—C18—C19	−16.3 (3)
C11—N3—C7—C8	0.3 (3)	C13—C12—C18—C19	165.1 (2)
Fe1—N3—C7—C8	−178.85 (18)	C18—C12—O23—C24	139.3 (2)
C11—N3—C7—C6	176.80 (19)	C13—C12—O23—C24	−42.0 (3)
Fe1—N3—C7—C6	−2.3 (2)	C12—O23—C24—C25	−135.0 (2)
N2—C6—C7—N3	40.0 (2)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N15ⁱⁱ	0.86 (4)	2.12 (4)	2.976 (3)	172 (3)
O1—H2···N17	0.84 (4)	2.09 (4)	2.921 (3)	175 (4)
N2—H2B···O1ⁱⁱⁱ	0.91	2.25	3.065 (3)	149
N2—H2C···N20^iv	0.91	2.38	3.184 (3)	148
N2—H2C···O1	0.91	2.47	2.958 (3)	114

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

Acknowledgements

JPJ acknowledges the NSF–MRI program (grant No. CHE-1039027) for funds to purchase the X-ray diffractometer.

Funding information

FS gratefully acknowledges the Algerian DGRSDT (Direction Générale de la Recherche Scientifique et du Développement Technologique) and Université Ferhat Abbas Sétif 1 for financial support.

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