trans-Bis{2-[bis(1H-pyrazol-1-yl)methyl]-1-methyl-1H-benzimidazole}­iron(II) bis(perchlorate) aceto­nitrile disolvate

Kumar, A.; Faizi, M.S.H.; Javed, S.; Siddiqui, N.; Iskenderov, T.

doi:10.1107/S2414314619000506

metal-organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 4| Part 1| January 2019| x190050

https://doi.org/10.1107/S2414314619000506

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trans-Bis{2-[bis(1H-pyrazol-1-yl)methyl]-1-methyl-1H-benzimidazole}iron(II) bis(perchlorate) acetonitrile disolvate

Akhilesh Kumar,^a Md. Serajul Haque Faizi,^b ^* Saleem Javed,^c Nazia Siddiqui ^c and Turganbay Iskenderov ^d ^*

^aDepartment of Chemistry, Indian Institute of Technology Kanpur 208016, UP, India, ^bDepartment of Chemistry, Langat Singh College, B. R. A. Bihar University, Muzaffarpur, Bihar 842001, India, ^cDepartment of Chemistry, IHS, Khandari, Dr. Bhimrao Ambedkar University, Agra 208016, India, and ^dNational Taras Shevchenko University, Department of Chemistry, Volodymyrska str. 64, 01601 Kyiv, Ukraine
^*Correspondence e-mail: faizichemiitg@gmail.com, tiskenderov@ukr.net

Edited by W. Imhof, University Koblenz-Landau, Germany (Received 26 December 2018; accepted 9 January 2019; online 15 January 2019)

In the structure of the title complex, [Fe(C₁₅H₁₄N₆)₂](ClO₄)₂·2C₂H₃N, the asymmetric unit contains one complete ligand molecule, one perchlorate and one acetonitrile solvent molecule. The iron(II) atom, situated on an inversion centre, is surrounded by six nitrogen atoms from two ligands in an octahedral coordination sphere in which the two benzimidazole units adopt a trans-configuration. The crystal structure is stablized by extensive weak C—H⋯O and C—H⋯N interactions.

Keywords: crystal structure; nitrogen heterocyclic compounds; benzimidazole; pyrazole; iron(II) complex.

CCDC reference: 1886880

Structure description

Spin-crossover (SCO) complexes are an important class of compounds with respect to new molecular materials and nanoscience research. Moreover, SCO complexes exhibit electronic transitions that involve a change of the spin state at the metal ion in a material, causing changes in a number of its physical properties including its colour, magnetism and conductivity (Guionneau, 2014 ; Kahn & Martinez, 1998 ; Matsuda & Tajima, 2007 ). The present work is part of an ongoing structural study of heterocyclic compounds (Faizi et al., 2016 ) and their utilization in the synthesis of metal complexes (Faizi & Prisyazhnaya, 2015 ), excited-state proton-transfer compounds and fluorescent chemosensors (Faizi et al., 2018 ; Kumar et al., 2018 ; Mukherjee et al., 2018 ). Herein we report the synthesis and crystal structure of a new Fe^II complex with 2-(di-pyrazol-1-yl-methyl)-1-methyl-1H-benzo[d]imidazole ligands.

The title compound (Fig. 1) crystallizes in the monoclinic space group P2₁/c. The asymmetric unit contains one complete ligand molecule, one perchlorate and one acetonitrile solvent molecule. As the iron(II) atom is situated on a crystallographic centre of inversion, another ligand, the second perchlorate and another solvent molecule are observed as symmetry equivalents. The iron(II) atom is surrounded by six nitrogen atoms from two ligands in an octahedral coordination sphere in which the two benzimidazole units adopt a trans-configuration. The non-coordinating perchlorate counter-ions and solvent molecules connect the complex molecules through weak C—H⋯O and C—H⋯N hydrogen-bonding interactions (Table 1, Fig. 2).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯N7ⁱ	0.95	2.57	3.494 (3)	164
C4—H4⋯O1ⁱⁱ	0.95	2.42	3.308 (3)	155
C5—H5⋯O3ⁱⁱⁱ	0.95	2.60	3.449 (3)	149
C7—H7⋯O4ⁱⁱ	1.00	2.32	3.308 (3)	170
C16—H16A⋯O1^iv	0.98	2.40	3.300 (3)	152
C16—H16B⋯O3	0.98	2.47	3.303 (3)	143
Symmetry codes: (i) -x+1, -y, -z+1; (ii) -x, -y+1, -z+1; (iii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iv) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Figure 1
The molecular structure of the title compound, showing the atom-labelling scheme and displacement ellipsoids at the 40% probability level for non-H atoms. H atoms are omitted for the sake of clarity. [Symmetry code: (′) −x + 1, −y + 1, −z + 1.].

Figure 2
A view along the a axis, emphasizing the weak C—H⋯O and C—H⋯N interactions which promote the crystal packing in the unit cell of the title compound. Only H atoms involved in these interactions are shown.

Synthesis and crystallization

To a stirred solution of 2-(di-pyrazol-1-yl-methyl)-1-methyl-1H-benzo[d]imidazole (100 mg, 0.36 mmol) in methanol (3 ml) solid [Fe^II(H₂O)₆](ClO₄)₂ (65 mg, 0.18 mmol) was added in small portions under nitrogen. The colour of the solution turned from light yellow to dark yellow without any observed precipitation. After 15 min of stirring, 3 ml of diethyl ether was added, leading to a bright-yellow precipitate that was collected by filtration, washed with 2 ml of methanol/diethyl ether (1:5) and dried in vacuo (yield: 110 mg, 78%). The title compound was recrystallized from an acetonitrile/toluene/diethyl ether (4:1:1) mixture (yield: 75 mg, 53%).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	[Fe(C₁₅H₁₄N₆)₂](ClO₄)₂·2C₂H₃N
M_r	893.50
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	11.3128 (5), 11.7818 (5), 14.1459 (6)
β (°)	99.965 (1)
V (Å³)	1856.99 (14)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.62
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Bruker SMART APEX CCD area detector
No. of measured, independent and observed [I > 2σ(I)] reflections	23607, 3638, 3137
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.076, 1.06
No. of reflections	3638
No. of parameters	270
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.43
Computer programs: APEX and SMART (Bruker, 2007 ), SAINT-Plus (Bruker, 2007), SHELXT2014/5 (Sheldrick, 2015a ), SHELXL2018/3 (Sheldrick, 2015b ) and ORTEP-3 for Windows and WinGX publication routines (Farrugia, 2012 ).

Structural data

CCDC reference: 1886880

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314619000506/im4002sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314619000506/im4002Isup2.hkl

checkCIF report

Computing details top

Data collection: APEX (Bruker, 2007); cell refinement: SMART (Bruker, 2007); data reduction: SAINT-Plus (Bruker, 2007); program(s) used to solve structure: SHELXT2014/5 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX publication routines (Farrugia, 2012).

trans-Bis{2-[bis(1H-pyrazol-1-yl)methyl]-1-methyl-1H-benzimidazole}iron(II) bis(perchlorate) acetonitrile disolvate top

Crystal data top

[Fe(C₃₀H₂₈N₁₂)](ClO₄)₂·2C₂H₃N	F(000) = 920
M_r = 893.50	D_x = 1.598 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.3128 (5) Å	Cell parameters from 819 reflections
b = 11.7818 (5) Å	θ = 2.4–20.7°
c = 14.1459 (6) Å	µ = 0.62 mm⁻¹
β = 99.965 (1)°	T = 100 K
V = 1856.99 (14) Å³	Prism, brown
Z = 2	0.3 × 0.25 × 0.2 mm

Data collection top

Bruker SMART APEX CCD area detector diffractometer	3137 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.042
Graphite monochromator	θ_max = 26.0°, θ_min = 2.9°
phi and ω scans	h = −13→13
23607 measured reflections	k = −14→14
3638 independent reflections	l = −17→17

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.035	H-atom parameters constrained
wR(F²) = 0.076	w = 1/[σ²(F_o²) + (0.0168P)² + 2.7931P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
3638 reflections	Δρ_max = 0.41 e Å⁻³
270 parameters	Δρ_min = −0.42 e Å⁻³

Special details top

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

Refinement. All non-hydrogen atoms were refined anisotropically. All H atoms were placed in calculated positions with d(C—H) = 0.95 Å for aromatic, 0.99 for CH and 0.98 Å for CH₃ hydrogen atoms. The U_iso values were constrained to be 1.5U_eq of the carrier atom for methyl H atoms and 1.2U_eq for the remaining H atoms. A rotating group model was used for the methyl groups.

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	0.00973 (11)
Cl1	0.05039 (5)	0.27781 (5)	0.40185 (4)	0.01701 (13)
O3	0.12532 (15)	0.19176 (15)	0.37156 (12)	0.0279 (4)
O4	−0.03438 (16)	0.22572 (16)	0.45362 (13)	0.0321 (4)
N1	0.37147 (15)	0.69590 (15)	0.54879 (12)	0.0125 (4)
N5	0.17075 (15)	0.58282 (15)	0.35199 (12)	0.0132 (4)
N3	0.29224 (15)	0.52189 (14)	0.59044 (12)	0.0119 (4)
N2	0.48187 (15)	0.65942 (15)	0.53656 (12)	0.0119 (4)
N6	0.35795 (15)	0.52172 (14)	0.40051 (12)	0.0115 (4)
N4	0.39132 (15)	0.45709 (15)	0.58812 (12)	0.0120 (4)
O2	0.12218 (17)	0.35829 (16)	0.46189 (13)	0.0358 (5)
C2	0.4930 (2)	0.83730 (19)	0.59389 (15)	0.0172 (5)
H2	0.524998	0.908882	0.616231	0.021*
C9	0.32286 (18)	0.49076 (17)	0.30497 (14)	0.0131 (4)
C11	0.3218 (2)	0.41027 (18)	0.15131 (15)	0.0186 (5)
H11	0.360895	0.370447	0.107091	0.022*
C1	0.3762 (2)	0.80282 (18)	0.58468 (15)	0.0160 (4)
H1	0.311041	0.845477	0.600384	0.019*
C12	0.2026 (2)	0.44547 (19)	0.12219 (15)	0.0195 (5)
H12	0.162356	0.427008	0.059441	0.023*
N7	0.3653 (2)	−0.19358 (19)	0.32491 (16)	0.0336 (5)
C10	0.3839 (2)	0.43188 (18)	0.24239 (15)	0.0160 (5)
H10	0.464626	0.407797	0.261703	0.019*
C14	0.20482 (19)	0.52798 (17)	0.27436 (15)	0.0135 (4)
C3	0.55583 (19)	0.74560 (18)	0.56368 (15)	0.0150 (4)
H3	0.639584	0.745042	0.562708	0.018*
C17	0.2894 (2)	−0.1444 (2)	0.34915 (16)	0.0214 (5)
C6	0.38856 (19)	0.37666 (18)	0.65344 (15)	0.0148 (4)
H6	0.447066	0.318586	0.668362	0.018*
C4	0.22846 (18)	0.48295 (18)	0.65559 (14)	0.0138 (4)
H4	0.156295	0.514501	0.669858	0.017*
C8	0.26536 (18)	0.57538 (17)	0.42446 (15)	0.0117 (4)
C5	0.28718 (19)	0.38935 (18)	0.69738 (15)	0.0156 (4)
H5	0.264205	0.342743	0.745928	0.019*
C13	0.1422 (2)	0.50623 (19)	0.18237 (15)	0.0173 (5)
H13	0.062226	0.531874	0.162153	0.021*
C7	0.27116 (18)	0.61768 (18)	0.52547 (14)	0.0124 (4)
H7	0.194396	0.656411	0.532181	0.015*
C15	0.05201 (19)	0.6289 (2)	0.35561 (16)	0.0196 (5)
H15A	0.001099	0.621263	0.292431	0.029*
H15B	0.059185	0.709316	0.373456	0.029*
H15C	0.015932	0.587172	0.403368	0.029*
C16	0.1912 (2)	−0.0816 (2)	0.37885 (17)	0.0266 (6)
H16A	0.118696	−0.090154	0.330248	0.040*
H16B	0.212640	−0.001088	0.385914	0.040*
H16C	0.176149	−0.111334	0.440372	0.040*
O1	−0.01354 (18)	0.33506 (17)	0.31901 (13)	0.0409 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe1	0.0089 (2)	0.0101 (2)	0.0108 (2)	0.00113 (16)	0.00303 (15)	0.00068 (17)
Cl1	0.0179 (3)	0.0173 (3)	0.0160 (3)	0.0022 (2)	0.0032 (2)	−0.0024 (2)
O3	0.0238 (9)	0.0270 (9)	0.0349 (10)	0.0101 (7)	0.0110 (8)	−0.0015 (8)
O4	0.0296 (10)	0.0327 (10)	0.0387 (11)	−0.0091 (8)	0.0191 (8)	−0.0085 (9)
N1	0.0120 (9)	0.0127 (9)	0.0134 (9)	0.0026 (7)	0.0038 (7)	−0.0003 (7)
N5	0.0110 (9)	0.0147 (9)	0.0140 (9)	0.0001 (7)	0.0026 (7)	0.0017 (7)
N3	0.0108 (8)	0.0124 (9)	0.0132 (8)	0.0011 (7)	0.0040 (7)	−0.0005 (7)
N2	0.0098 (8)	0.0138 (9)	0.0127 (8)	0.0019 (7)	0.0035 (7)	0.0016 (7)
N6	0.0122 (9)	0.0111 (9)	0.0119 (8)	0.0005 (7)	0.0037 (7)	−0.0004 (7)
N4	0.0092 (8)	0.0132 (9)	0.0137 (9)	0.0019 (7)	0.0025 (7)	−0.0001 (7)
O2	0.0447 (11)	0.0334 (11)	0.0293 (10)	−0.0195 (9)	0.0058 (8)	−0.0111 (8)
C2	0.0213 (12)	0.0139 (11)	0.0157 (11)	−0.0021 (9)	0.0011 (9)	−0.0026 (9)
C9	0.0157 (10)	0.0106 (10)	0.0131 (10)	−0.0031 (9)	0.0023 (8)	0.0017 (8)
C11	0.0309 (13)	0.0124 (11)	0.0134 (10)	0.0001 (10)	0.0068 (9)	−0.0006 (9)
C1	0.0214 (11)	0.0134 (10)	0.0133 (10)	0.0040 (9)	0.0033 (9)	0.0000 (9)
C12	0.0298 (13)	0.0156 (11)	0.0120 (10)	−0.0055 (10)	0.0004 (9)	−0.0001 (9)
N7	0.0341 (13)	0.0322 (13)	0.0373 (13)	0.0105 (11)	0.0144 (10)	0.0127 (11)
C10	0.0208 (11)	0.0115 (10)	0.0168 (11)	−0.0002 (9)	0.0060 (9)	0.0019 (9)
C14	0.0159 (11)	0.0106 (10)	0.0150 (10)	−0.0017 (8)	0.0055 (8)	0.0015 (8)
C3	0.0156 (11)	0.0161 (11)	0.0128 (10)	−0.0017 (9)	0.0010 (8)	0.0022 (8)
C17	0.0261 (13)	0.0195 (12)	0.0186 (11)	0.0007 (10)	0.0037 (10)	0.0073 (10)
C6	0.0164 (11)	0.0127 (10)	0.0149 (10)	0.0001 (9)	0.0014 (8)	0.0010 (9)
C4	0.0120 (10)	0.0174 (11)	0.0136 (10)	−0.0020 (8)	0.0062 (8)	−0.0022 (9)
C8	0.0111 (10)	0.0104 (10)	0.0139 (10)	0.0005 (8)	0.0028 (8)	0.0024 (8)
C5	0.0169 (11)	0.0156 (11)	0.0152 (10)	−0.0028 (9)	0.0056 (8)	0.0009 (9)
C13	0.0175 (11)	0.0155 (11)	0.0177 (11)	−0.0042 (9)	−0.0006 (9)	0.0040 (9)
C7	0.0102 (10)	0.0131 (10)	0.0140 (10)	0.0011 (8)	0.0025 (8)	0.0012 (8)
C15	0.0120 (11)	0.0216 (12)	0.0241 (12)	0.0021 (9)	0.0003 (9)	−0.0010 (10)
C16	0.0309 (14)	0.0284 (14)	0.0217 (12)	0.0078 (11)	0.0076 (10)	0.0022 (10)
O1	0.0475 (12)	0.0425 (12)	0.0287 (10)	0.0233 (10)	−0.0045 (9)	0.0034 (9)

Geometric parameters (Å, º) top

Fe1—N6ⁱ	1.9610 (17)	C9—C14	1.401 (3)
Fe1—N6	1.9610 (17)	C11—C10	1.380 (3)
Fe1—N4ⁱ	1.9626 (17)	C11—C12	1.403 (3)
Fe1—N4	1.9626 (17)	C11—H11	0.9500
Fe1—N2	1.9683 (17)	C1—H1	0.9500
Fe1—N2ⁱ	1.9683 (17)	C12—C13	1.380 (3)
Cl1—O2	1.4287 (18)	C12—H12	0.9500
Cl1—O3	1.4338 (17)	N7—C17	1.136 (3)
Cl1—O1	1.4346 (18)	C10—H10	0.9500
Cl1—O4	1.4407 (17)	C14—C13	1.393 (3)
N1—C1	1.356 (3)	C3—H3	0.9500
N1—N2	1.360 (2)	C17—C16	1.456 (3)
N1—C7	1.455 (3)	C6—C5	1.404 (3)
N5—C8	1.351 (3)	C6—H6	0.9500
N5—C14	1.385 (3)	C4—C5	1.368 (3)
N5—C15	1.458 (3)	C4—H4	0.9500
N3—C4	1.346 (3)	C8—C7	1.504 (3)
N3—N4	1.361 (2)	C5—H5	0.9500
N3—C7	1.449 (3)	C13—H13	0.9500
N2—C3	1.329 (3)	C7—H7	1.0000
N6—C8	1.317 (3)	C15—H15A	0.9800
N6—C9	1.390 (3)	C15—H15B	0.9800
N4—C6	1.328 (3)	C15—H15C	0.9800
C2—C1	1.367 (3)	C16—H16A	0.9800
C2—C3	1.400 (3)	C16—H16B	0.9800
C2—H2	0.9500	C16—H16C	0.9800
C9—C10	1.398 (3)

N6ⁱ—Fe1—N6	180.0	N1—C1—H1	126.7
N6ⁱ—Fe1—N4ⁱ	87.92 (7)	C2—C1—H1	126.7
N6—Fe1—N4ⁱ	92.08 (7)	C13—C12—C11	121.7 (2)
N6ⁱ—Fe1—N4	92.08 (7)	C13—C12—H12	119.2
N6—Fe1—N4	87.93 (7)	C11—C12—H12	119.2
N4ⁱ—Fe1—N4	180.0	C11—C10—C9	117.1 (2)
N6ⁱ—Fe1—N2	92.62 (7)	C11—C10—H10	121.5
N6—Fe1—N2	87.38 (7)	C9—C10—H10	121.5
N4ⁱ—Fe1—N2	91.51 (7)	N5—C14—C13	131.3 (2)
N4—Fe1—N2	88.49 (7)	N5—C14—C9	106.38 (18)
N6ⁱ—Fe1—N2ⁱ	87.38 (7)	C13—C14—C9	122.3 (2)
N6—Fe1—N2ⁱ	92.62 (7)	N2—C3—C2	110.49 (19)
N4ⁱ—Fe1—N2ⁱ	88.49 (7)	N2—C3—H3	124.8
N4—Fe1—N2ⁱ	91.51 (7)	C2—C3—H3	124.8
N2—Fe1—N2ⁱ	180.0	N7—C17—C16	179.2 (3)
O2—Cl1—O3	110.02 (12)	N4—C6—C5	110.58 (19)
O2—Cl1—O1	109.14 (12)	N4—C6—H6	124.7
O3—Cl1—O1	109.20 (11)	C5—C6—H6	124.7
O2—Cl1—O4	109.90 (11)	N3—C4—C5	107.04 (18)
O3—Cl1—O4	109.31 (11)	N3—C4—H4	126.5
O1—Cl1—O4	109.24 (12)	C5—C4—H4	126.5
C1—N1—N2	111.32 (17)	N6—C8—N5	113.39 (18)
C1—N1—C7	130.72 (18)	N6—C8—C7	119.84 (18)
N2—N1—C7	117.93 (16)	N5—C8—C7	126.74 (18)
C8—N5—C14	106.19 (17)	C4—C5—C6	105.50 (19)
C8—N5—C15	127.69 (18)	C4—C5—H5	127.2
C14—N5—C15	125.87 (18)	C6—C5—H5	127.2
C4—N3—N4	111.51 (17)	C12—C13—C14	116.5 (2)
C4—N3—C7	130.63 (17)	C12—C13—H13	121.8
N4—N3—C7	117.87 (16)	C14—C13—H13	121.8
C3—N2—N1	105.54 (17)	N3—C7—N1	108.26 (16)
C3—N2—Fe1	135.70 (15)	N3—C7—C8	108.66 (17)
N1—N2—Fe1	118.35 (13)	N1—C7—C8	109.23 (16)
C8—N6—C9	105.67 (17)	N3—C7—H7	110.2
C8—N6—Fe1	117.87 (14)	N1—C7—H7	110.2
C9—N6—Fe1	136.41 (14)	C8—C7—H7	110.2
C6—N4—N3	105.37 (16)	N5—C15—H15A	109.5
C6—N4—Fe1	135.95 (15)	N5—C15—H15B	109.5
N3—N4—Fe1	118.67 (13)	H15A—C15—H15B	109.5
C1—C2—C3	105.95 (19)	N5—C15—H15C	109.5
C1—C2—H2	127.0	H15A—C15—H15C	109.5
C3—C2—H2	127.0	H15B—C15—H15C	109.5
N6—C9—C10	131.1 (2)	C17—C16—H16A	109.5
N6—C9—C14	108.36 (18)	C17—C16—H16B	109.5
C10—C9—C14	120.58 (19)	H16A—C16—H16B	109.5
C10—C11—C12	121.8 (2)	C17—C16—H16C	109.5
C10—C11—H11	119.1	H16A—C16—H16C	109.5
C12—C11—H11	119.1	H16B—C16—H16C	109.5
N1—C1—C2	106.68 (19)

C1—N1—N2—C3	−1.1 (2)	N3—N4—C6—C5	0.4 (2)
C7—N1—N2—C3	−179.34 (17)	Fe1—N4—C6—C5	178.59 (16)
C1—N1—N2—Fe1	172.72 (13)	N4—N3—C4—C5	−0.1 (2)
C7—N1—N2—Fe1	−5.6 (2)	C7—N3—C4—C5	179.51 (19)
C4—N3—N4—C6	−0.1 (2)	C9—N6—C8—N5	−0.1 (2)
C7—N3—N4—C6	−179.84 (17)	Fe1—N6—C8—N5	−177.98 (13)
C4—N3—N4—Fe1	−178.73 (13)	C9—N6—C8—C7	177.93 (18)
C7—N3—N4—Fe1	1.6 (2)	Fe1—N6—C8—C7	0.0 (2)
C8—N6—C9—C10	−179.7 (2)	C14—N5—C8—N6	0.6 (2)
Fe1—N6—C9—C10	−2.4 (4)	C15—N5—C8—N6	175.19 (19)
C8—N6—C9—C14	−0.5 (2)	C14—N5—C8—C7	−177.20 (19)
Fe1—N6—C9—C14	176.79 (15)	C15—N5—C8—C7	−2.6 (3)
N2—N1—C1—C2	1.4 (2)	N3—C4—C5—C6	0.4 (2)
C7—N1—C1—C2	179.36 (19)	N4—C6—C5—C4	−0.5 (2)
C3—C2—C1—N1	−1.1 (2)	C11—C12—C13—C14	−1.7 (3)
C10—C11—C12—C13	1.8 (3)	N5—C14—C13—C12	−178.1 (2)
C12—C11—C10—C9	0.0 (3)	C9—C14—C13—C12	0.1 (3)
N6—C9—C10—C11	177.5 (2)	C4—N3—C7—N1	118.7 (2)
C14—C9—C10—C11	−1.6 (3)	N4—N3—C7—N1	−61.6 (2)
C8—N5—C14—C13	177.5 (2)	C4—N3—C7—C8	−122.7 (2)
C15—N5—C14—C13	2.8 (4)	N4—N3—C7—C8	56.9 (2)
C8—N5—C14—C9	−0.9 (2)	C1—N1—C7—N3	−113.8 (2)
C15—N5—C14—C9	−175.60 (19)	N2—N1—C7—N3	64.1 (2)
N6—C9—C14—N5	0.9 (2)	C1—N1—C7—C8	128.1 (2)
C10—C9—C14—N5	−179.82 (18)	N2—N1—C7—C8	−54.0 (2)
N6—C9—C14—C13	−177.68 (19)	N6—C8—C7—N3	−59.2 (2)
C10—C9—C14—C13	1.6 (3)	N5—C8—C7—N3	118.5 (2)
N1—N2—C3—C2	0.3 (2)	N6—C8—C7—N1	58.7 (2)
Fe1—N2—C3—C2	−171.80 (15)	N5—C8—C7—N1	−123.6 (2)
C1—C2—C3—N2	0.5 (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
C6—H6···N7ⁱⁱ	0.95	2.57	3.494 (3)	164
C4—H4···O1ⁱⁱⁱ	0.95	2.42	3.308 (3)	155
C5—H5···O3^iv	0.95	2.60	3.449 (3)	149
C7—H7···O4ⁱⁱⁱ	1.00	2.32	3.308 (3)	170
C16—H16A···O1^v	0.98	2.40	3.300 (3)	152
C16—H16B···O3	0.98	2.47	3.303 (3)	143

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

Acknowledgements

The authors are grateful to the National Taras Shevchenko University, Department of Chemistry, for financial support. Additional support by the Department of Chemistry, L. S. College, B. R. A. Bihar University, Muzaffarpur, India, and the Department of Chemistry, IHS, Khandari, Dr. Bhimrao Ambedkar University, Agra, India, for providing laboratory facilities is also gratefully acknowledged.

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