metal-organic compounds
fac-Bis[bis(pyridin-2-yl)methanamine]iron(II) bis(1,1,3,3-tetracyano-2-ethoxypropenide) dihydrate
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
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 FeII 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 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 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 (FeII, CoIII, NiII, CuII: Bernhardt et al., 1992; FeIII: Renz et al., 1999; MnII: 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°).
The water molecule behaves both as donor and acceptor for hydrogen bonding, stabilizing the and Fig. 2).
with three weak hydrogen bonds involving two symmetry-related tcnoet anions and the central amine group of the DIPA ligand (Table 1Synthesis 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 . Two reflections ( 9 1, 9 1) were omitted because of poor agreement between calculated and observed intensities.
details are summarized in Table 2Structural data
CCDC reference: 1560707
https://doi.org/10.1107/S2414314617010070/wm4052sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617010070/wm4052Isup2.hkl
Data collection: CrysAlis PRO (Rigaku OD, 2015); cell
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).[Fe(C11H11N3)2](C9H5N4O)2·2H2O | F(000) = 864 |
Mr = 832.68 | Dx = 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 |
Agilent Xcalibur diffractometer | 3799 independent reflections |
Radiation source: Enhance (Cu) X-ray Source | 3393 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.025 |
Detector resolution: 16.0416 pixels mm-1 | θmax = 71.5°, θmin = 3.8° |
ω scans | h = −8→14 |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015) | k = −9→9 |
Tmin = 0.843, Tmax = 1.000 | l = −27→26 |
8154 measured reflections |
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(Fo2) + (0.0542P)2 + 1.1004P] where P = (Fo2 + 2Fc2)/3 |
3799 reflections | (Δ/σ)max < 0.001 |
275 parameters | Δρmax = 0.45 e Å−3 |
0 restraints | Δρmin = −0.32 e Å−3 |
0 constraints |
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. |
x | y | z | Uiso*/Ueq | ||
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* |
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) |
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. |
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···N20iv | 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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