Tris(5,6-dimethyl-1,10-phenanthroline-κ(2) N,N')iron(II) bis-(tricyano-methanide).

The title compound, [Fe(C14H12N2)3](C4N3)2, consists of one [Fe(dimephen)3](2+) complex cation (dimephen = 5,6-dimethyl-1,10-phenanthroline) and two uncoordinating tcm anions (tcm = tricyano-methanide). In the complex cation, the Fe(II) atom is coordinated by six N atoms from three chelating dimephen ligands at an average Fe-N distance of 1.963 (4) Å giving a distorted octa-hedral geometry. The crystal structure is stabilized by weak C-H⋯N hydrogen bonds and C N⋯π inter-actions between planar [maximum deviations of 0.024 (3) and 0.015 (3) Å] tcm anions and pyridine rings of dimephen [N2⋯centroid = 3.531 (3) and 3.726 (3) Å; C N⋯centroid = 96.4 (2) and 97.1 (2)°].

Related literature

[Fe(phen)2(n class="Chemical">NCS)2] (phen = 1,10-phenathroline) and [Fe(bpy)2(NCS)2] (bpy = 2,2-bipyridine) are the first known and most extensively studied compounds of iron(II) exhibiting a high spin ←→ low spin transition, see: König & Watson (1970 ▶); Müller et al. (1982 ▶). For [Fe(phen)3]2+complexes, see: Aparici Plaza et al. (2007 ▶); Odoko & Okabe (2004 ▶); Koh et al. (1994 ▶); Uçar et al. (2005 ▶); Li et al. (2008 ▶). For bond lengths and angles in dimephen, see: Toledano-Magaña et al. (2012) ▶ and in tcm ligands, see: Potočňák et al. (2002 ▶); Luo et al. (2009 ▶). For the structure, properties and bonding modes of the tcm anion, see: Golub et al. (1986 ▶); Kohout et al. (2000 ▶). For the crystal and mol­ecular structure of phen, see: Nishigaki et al. (1978 ▶). For similar FeII complexes, see: Váhovská & Potočňák (2012 ▶).

Experimental

Crystal data

[Fe(C14H12N2)3](C4N3)2

M = 860.76

Triclinic,

a = 9.3676 (3) Å

b = 12.7079 (9) Å

c = 18.1998 (9) Å

α = 75.458 (5)°

β = 89.623 (3)°

γ = 82.323 (4)°

V = 2077.52 (19) Å3

Z = 2

Mo Kα radiation

μ = 0.42 mm−1

T = 183 K

0.66 × 0.25 × 0.03 mm

Data collection

Agilent Xcalibur (Sapphire2) diffractometer

Absorption correction: analytical [CrysAlis PRO (Agilent, 2012 ▶), based on expressions derived by Clark & Reid (1995 ▶)] T min = 0.874, T max = 0.986

15408 measured reflections

8167 independent reflections

6309 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.125

S = 1.07

8167 reflections

574 parameters

H-atom parameters constrained

Δρmax = 0.92 e Å−3

Δρmin = −0.40 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2001 ▶); software used to prepare material for publication: SHELXL97.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812046880/bx2428sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812046880/bx2428Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Fe(C14H12N2)3](C4N3)2	Z = 2
Mr = 860.76	F(000) = 892
Triclinic, P1	Dx = 1.376 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.3676 (3) Å	Cell parameters from 5036 reflections
b = 12.7079 (9) Å	θ = 3.0–29.2°
c = 18.1998 (9) Å	µ = 0.42 mm−1
α = 75.458 (5)°	T = 183 K
β = 89.623 (3)°	Needle, dark red
γ = 82.323 (4)°	0.66 × 0.25 × 0.03 mm
V = 2077.52 (19) Å3

Agilent Xcalibur (Sapphire2) diffractometer	8167 independent reflections
Radiation source: fine-focus sealed tube	6309 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
Detector resolution: 8.3438 pixels mm-1	θmax = 26.0°, θmin = 3.0°
ω scans	h = −11→11
Absorption correction: analytical [CrysAlis PRO (Agilent, 2012), based on expressions derived by Clark & Reid (1995)]	k = −15→10
Tmin = 0.874, Tmax = 0.986	l = −22→21
15408 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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0473P)2 + 1.1913P] where P = (Fo2 + 2Fc2)/3
8167 reflections	(Δ/σ)max = 0.001
574 parameters	Δρmax = 0.92 e Å−3
0 restraints	Δρmin = −0.40 e Å−3

Experimental. CrysAlis PRO (Agilent, 2012) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)

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.

	x	y	z	Uiso*/Ueq
Fe1	0.52758 (4)	0.38724 (3)	0.27263 (2)	0.01786 (11)
N10	0.6319 (2)	0.51196 (18)	0.23141 (12)	0.0199 (5)
N20	0.3666 (2)	0.50317 (18)	0.27106 (12)	0.0196 (5)
N30	0.5692 (2)	0.37913 (18)	0.37975 (12)	0.0208 (5)
N40	0.4163 (2)	0.26722 (18)	0.31777 (12)	0.0189 (5)
N50	0.6912 (2)	0.27509 (18)	0.26764 (12)	0.0196 (5)
N60	0.4893 (2)	0.37825 (18)	0.16864 (12)	0.0191 (5)
C11	0.5467 (3)	0.6115 (2)	0.22050 (14)	0.0178 (5)
C12	0.7678 (3)	0.5128 (2)	0.20913 (15)	0.0250 (6)
H12	0.8295	0.4451	0.2168	0.030*
C13	0.8222 (3)	0.6097 (2)	0.17501 (16)	0.0279 (7)
H13	0.9186	0.6070	0.1583	0.034*
C14	0.7372 (3)	0.7085 (2)	0.16549 (16)	0.0273 (7)
H14	0.7750	0.7746	0.1430	0.033*
C15	0.5938 (3)	0.7123 (2)	0.18903 (14)	0.0204 (6)
C16	0.4937 (3)	0.8123 (2)	0.18188 (15)	0.0235 (6)
C17	0.5497 (3)	0.9199 (3)	0.14961 (18)	0.0365 (8)
H17A	0.4687	0.9793	0.1376	0.055*
H17B	0.6020	0.9165	0.1033	0.055*
H17C	0.6148	0.9337	0.1870	0.055*
C21	0.4017 (3)	0.6066 (2)	0.24352 (14)	0.0184 (6)
C22	0.2318 (3)	0.4941 (2)	0.29416 (16)	0.0255 (6)
H22	0.2046	0.4230	0.3132	0.031*
C23	0.1304 (3)	0.5858 (3)	0.29106 (17)	0.0297 (7)
H23	0.0362	0.5767	0.3089	0.036*
C24	0.1652 (3)	0.6885 (3)	0.26263 (16)	0.0284 (7)
H24	0.0952	0.7508	0.2603	0.034*
C25	0.3061 (3)	0.7028 (2)	0.23650 (15)	0.0209 (6)
C26	0.3543 (3)	0.8075 (2)	0.20441 (15)	0.0245 (6)
C27	0.2448 (3)	0.9083 (3)	0.19628 (19)	0.0389 (8)
H27A	0.2917	0.9740	0.1775	0.058*
H27B	0.2035	0.9090	0.2458	0.058*
H27C	0.1680	0.9073	0.1602	0.058*
C31	0.5127 (3)	0.2963 (2)	0.42907 (14)	0.0201 (6)
C32	0.6471 (3)	0.4402 (2)	0.40944 (16)	0.0257 (6)
H32	0.6869	0.4988	0.3763	0.031*
C33	0.6717 (3)	0.4202 (3)	0.48748 (17)	0.0326 (7)
H33	0.7272	0.4652	0.5067	0.039*
C34	0.6164 (3)	0.3365 (3)	0.53644 (17)	0.0320 (7)
H34	0.6342	0.3228	0.5896	0.038*
C35	0.5328 (3)	0.2702 (2)	0.50797 (15)	0.0266 (6)
C36	0.4690 (3)	0.1787 (3)	0.55442 (16)	0.0300 (7)
C37	0.4985 (3)	0.1533 (3)	0.63885 (17)	0.0434 (9)
H37A	0.4570	0.0871	0.6641	0.065*
H37B	0.4548	0.2151	0.6582	0.065*
H37C	0.6027	0.1411	0.6491	0.065*
C41	0.4288 (2)	0.2355 (2)	0.39481 (14)	0.0187 (6)
C42	0.3382 (3)	0.2126 (2)	0.28329 (16)	0.0256 (6)
H42	0.3264	0.2345	0.2296	0.031*
C43	0.2731 (3)	0.1237 (2)	0.32412 (18)	0.0301 (7)
H43	0.2195	0.0855	0.2978	0.036*
C44	0.2859 (3)	0.0914 (2)	0.40121 (17)	0.0293 (7)
H44	0.2412	0.0310	0.4285	0.035*
C45	0.3654 (3)	0.1477 (2)	0.44031 (16)	0.0243 (6)
C46	0.3868 (3)	0.1207 (2)	0.52172 (16)	0.0286 (7)
C47	0.3141 (3)	0.0276 (3)	0.56809 (19)	0.0422 (9)
H47A	0.3495	0.0093	0.6210	0.063*
H47B	0.3361	−0.0368	0.5475	0.063*
H47C	0.2097	0.0499	0.5659	0.063*
C51	0.6892 (3)	0.2399 (2)	0.20271 (15)	0.0188 (6)
C52	0.7946 (3)	0.2252 (2)	0.31962 (15)	0.0239 (6)
H52	0.7994	0.2494	0.3648	0.029*
C53	0.8950 (3)	0.1397 (2)	0.31027 (16)	0.0278 (7)
H53	0.9671	0.1066	0.3486	0.033*
C54	0.8910 (3)	0.1025 (2)	0.24603 (17)	0.0277 (7)
H54	0.9586	0.0426	0.2403	0.033*
C55	0.7863 (3)	0.1536 (2)	0.18851 (15)	0.0216 (6)
C56	0.7733 (3)	0.1236 (2)	0.11727 (16)	0.0258 (6)
C57	0.8814 (3)	0.0306 (3)	0.10493 (19)	0.0368 (8)
H57A	0.8544	0.0109	0.0587	0.055*
H57B	0.8824	−0.0332	0.1485	0.055*
H57C	0.9774	0.0537	0.0996	0.055*
C61	0.5799 (3)	0.2973 (2)	0.14812 (14)	0.0192 (6)
C62	0.3875 (3)	0.4362 (2)	0.11791 (15)	0.0232 (6)
H62	0.3234	0.4930	0.1307	0.028*
C63	0.3724 (3)	0.4158 (2)	0.04676 (16)	0.0289 (7)
H63	0.3001	0.4597	0.0117	0.035*
C64	0.4609 (3)	0.3332 (2)	0.02716 (16)	0.0272 (6)
H64	0.4491	0.3188	−0.0210	0.033*
C65	0.5700 (3)	0.2695 (2)	0.07885 (15)	0.0214 (6)
C66	0.6681 (3)	0.1789 (2)	0.06461 (16)	0.0252 (6)
C67	0.6472 (3)	0.1516 (3)	−0.00986 (18)	0.0382 (8)
H67A	0.7072	0.0823	−0.0100	0.057*
H67B	0.6751	0.2103	−0.0513	0.057*
H67C	0.5457	0.1444	−0.0169	0.057*
C1	0.0574 (3)	0.2816 (3)	0.04263 (18)	0.0358 (8)
C2	0.0526 (3)	0.3207 (3)	0.1087 (2)	0.0436 (9)
C3	−0.0500 (3)	0.3222 (3)	−0.0146 (2)	0.0438 (9)
C4	0.1662 (3)	0.1985 (3)	0.03535 (18)	0.0338 (7)
C5	0.9633 (3)	0.7346 (3)	0.44900 (18)	0.0325 (7)
C6	0.9720 (3)	0.6902 (3)	0.5285 (2)	0.0413 (8)
C7	1.0418 (3)	0.8197 (3)	0.41576 (19)	0.0348 (7)
C8	0.8731 (3)	0.6955 (3)	0.4037 (2)	0.0374 (8)
N2	0.0493 (3)	0.3516 (3)	0.1633 (2)	0.0640 (10)
N3	−0.1365 (3)	0.3538 (3)	−0.0629 (2)	0.0624 (10)
N4	0.2554 (3)	0.1297 (2)	0.02865 (17)	0.0470 (7)
N6	0.9798 (3)	0.6547 (3)	0.5933 (2)	0.0670 (10)
N7	1.1049 (3)	0.8905 (2)	0.38654 (18)	0.0482 (8)
N8	0.7995 (3)	0.6636 (3)	0.36574 (19)	0.0508 (8)

	U11	U22	U33	U12	U13	U23
Fe1	0.01556 (18)	0.0189 (2)	0.0196 (2)	−0.00280 (14)	0.00151 (14)	−0.00547 (16)
N10	0.0156 (10)	0.0235 (13)	0.0207 (12)	−0.0017 (9)	0.0029 (8)	−0.0062 (10)
N20	0.0175 (10)	0.0233 (13)	0.0196 (12)	−0.0040 (9)	0.0034 (9)	−0.0076 (10)
N30	0.0171 (10)	0.0223 (13)	0.0242 (12)	−0.0025 (9)	0.0005 (9)	−0.0084 (10)
N40	0.0183 (10)	0.0186 (12)	0.0201 (12)	−0.0026 (9)	0.0005 (9)	−0.0053 (10)
N50	0.0179 (11)	0.0215 (13)	0.0194 (12)	−0.0052 (9)	0.0005 (9)	−0.0037 (10)
N60	0.0160 (10)	0.0191 (12)	0.0212 (12)	−0.0028 (9)	0.0024 (8)	−0.0031 (10)
C11	0.0196 (13)	0.0199 (15)	0.0146 (13)	−0.0021 (11)	−0.0009 (10)	−0.0061 (11)
C12	0.0175 (13)	0.0281 (17)	0.0293 (16)	−0.0011 (11)	0.0047 (11)	−0.0085 (13)
C13	0.0206 (14)	0.0351 (18)	0.0301 (16)	−0.0108 (13)	0.0078 (11)	−0.0084 (14)
C14	0.0287 (15)	0.0288 (17)	0.0254 (15)	−0.0153 (13)	0.0050 (12)	−0.0029 (13)
C15	0.0255 (13)	0.0234 (15)	0.0139 (13)	−0.0084 (11)	−0.0018 (10)	−0.0048 (11)
C16	0.0327 (15)	0.0222 (16)	0.0160 (14)	−0.0067 (12)	−0.0026 (11)	−0.0039 (12)
C17	0.0437 (18)	0.0239 (17)	0.0416 (19)	−0.0100 (14)	0.0025 (14)	−0.0050 (15)
C21	0.0198 (13)	0.0200 (15)	0.0161 (13)	−0.0027 (11)	−0.0002 (10)	−0.0061 (11)
C22	0.0199 (13)	0.0304 (17)	0.0282 (15)	−0.0060 (12)	0.0048 (11)	−0.0098 (13)
C23	0.0180 (13)	0.0391 (19)	0.0336 (17)	−0.0033 (12)	0.0059 (12)	−0.0125 (15)
C24	0.0200 (13)	0.0308 (18)	0.0341 (17)	0.0050 (12)	0.0018 (12)	−0.0119 (14)
C25	0.0223 (13)	0.0220 (15)	0.0184 (14)	0.0012 (11)	−0.0027 (10)	−0.0075 (12)
C26	0.0306 (15)	0.0230 (16)	0.0192 (14)	−0.0007 (12)	−0.0018 (11)	−0.0056 (12)
C27	0.0429 (18)	0.0287 (19)	0.0399 (19)	0.0068 (14)	0.0013 (14)	−0.0050 (15)
C31	0.0177 (12)	0.0223 (15)	0.0195 (14)	0.0006 (11)	0.0032 (10)	−0.0055 (12)
C32	0.0221 (13)	0.0271 (16)	0.0314 (16)	−0.0032 (12)	−0.0009 (11)	−0.0140 (13)
C33	0.0304 (15)	0.0380 (19)	0.0353 (18)	−0.0009 (13)	−0.0075 (13)	−0.0220 (15)
C34	0.0325 (16)	0.043 (2)	0.0219 (15)	0.0045 (14)	−0.0036 (12)	−0.0161 (15)
C35	0.0224 (14)	0.0332 (18)	0.0221 (15)	0.0061 (12)	−0.0005 (11)	−0.0084 (13)
C36	0.0256 (14)	0.0362 (19)	0.0209 (15)	0.0083 (13)	0.0044 (11)	−0.0006 (13)
C37	0.0424 (18)	0.057 (2)	0.0242 (17)	0.0025 (16)	0.0032 (14)	−0.0024 (16)
C41	0.0139 (12)	0.0195 (15)	0.0215 (14)	0.0005 (10)	0.0032 (10)	−0.0042 (11)
C42	0.0232 (14)	0.0291 (17)	0.0254 (15)	−0.0065 (12)	−0.0005 (11)	−0.0071 (13)
C43	0.0246 (14)	0.0270 (17)	0.0424 (19)	−0.0093 (12)	−0.0004 (12)	−0.0123 (14)
C44	0.0245 (14)	0.0219 (16)	0.0405 (18)	−0.0087 (12)	0.0082 (12)	−0.0033 (14)
C45	0.0180 (13)	0.0234 (16)	0.0286 (15)	0.0001 (11)	0.0050 (11)	−0.0029 (13)
C46	0.0231 (14)	0.0311 (17)	0.0254 (16)	0.0039 (12)	0.0060 (11)	0.0002 (13)
C47	0.0385 (17)	0.041 (2)	0.0369 (19)	−0.0039 (15)	0.0125 (14)	0.0073 (16)
C51	0.0170 (12)	0.0196 (14)	0.0216 (14)	−0.0074 (10)	0.0051 (10)	−0.0062 (11)
C52	0.0221 (13)	0.0296 (17)	0.0197 (14)	−0.0034 (12)	−0.0018 (11)	−0.0054 (12)
C53	0.0190 (13)	0.0322 (18)	0.0287 (16)	0.0007 (12)	−0.0032 (11)	−0.0029 (14)
C54	0.0201 (13)	0.0227 (16)	0.0393 (18)	0.0016 (11)	0.0034 (12)	−0.0082 (14)
C55	0.0177 (12)	0.0201 (15)	0.0276 (15)	−0.0054 (11)	0.0044 (11)	−0.0053 (12)
C56	0.0227 (14)	0.0236 (16)	0.0350 (17)	−0.0060 (11)	0.0085 (12)	−0.0132 (13)
C57	0.0303 (16)	0.038 (2)	0.049 (2)	−0.0019 (14)	0.0074 (14)	−0.0248 (17)
C61	0.0202 (13)	0.0167 (14)	0.0211 (14)	−0.0073 (10)	0.0056 (10)	−0.0033 (11)
C62	0.0221 (13)	0.0220 (15)	0.0246 (15)	−0.0028 (11)	−0.0002 (11)	−0.0040 (12)
C63	0.0287 (15)	0.0292 (17)	0.0256 (16)	−0.0056 (13)	−0.0060 (12)	−0.0001 (13)
C64	0.0330 (15)	0.0312 (17)	0.0190 (14)	−0.0096 (13)	−0.0005 (11)	−0.0064 (13)
C65	0.0235 (13)	0.0227 (15)	0.0200 (14)	−0.0095 (11)	0.0028 (10)	−0.0059 (12)
C66	0.0263 (14)	0.0258 (16)	0.0279 (16)	−0.0109 (12)	0.0076 (12)	−0.0113 (13)
C67	0.0456 (18)	0.041 (2)	0.0348 (18)	−0.0060 (15)	0.0022 (14)	−0.0212 (16)
C1	0.0270 (15)	0.0319 (19)	0.044 (2)	−0.0007 (13)	0.0069 (14)	−0.0022 (16)
C2	0.0298 (17)	0.040 (2)	0.056 (2)	0.0020 (15)	0.0137 (16)	−0.0059 (18)
C3	0.0318 (17)	0.032 (2)	0.056 (2)	−0.0013 (14)	0.0117 (16)	0.0075 (17)
C4	0.0314 (16)	0.0288 (18)	0.0372 (18)	−0.0050 (14)	0.0032 (13)	−0.0004 (15)
C5	0.0263 (15)	0.0321 (18)	0.0421 (19)	−0.0075 (13)	0.0061 (13)	−0.0132 (15)
C6	0.0290 (16)	0.043 (2)	0.054 (2)	−0.0148 (15)	0.0125 (15)	−0.0121 (18)
C7	0.0269 (15)	0.0275 (18)	0.051 (2)	−0.0034 (13)	0.0056 (14)	−0.0123 (16)
C8	0.0278 (16)	0.0316 (19)	0.055 (2)	−0.0055 (14)	0.0107 (15)	−0.0153 (17)
N2	0.055 (2)	0.069 (3)	0.074 (3)	−0.0022 (17)	0.0231 (18)	−0.032 (2)
N3	0.0396 (17)	0.061 (2)	0.068 (2)	0.0018 (15)	0.0005 (16)	0.0144 (19)
N4	0.0468 (17)	0.0364 (18)	0.0525 (19)	0.0050 (14)	0.0044 (14)	−0.0071 (15)
N6	0.059 (2)	0.088 (3)	0.055 (2)	−0.033 (2)	0.0127 (17)	−0.009 (2)
N7	0.0428 (16)	0.0360 (18)	0.066 (2)	−0.0129 (14)	0.0066 (14)	−0.0097 (16)
N8	0.0401 (16)	0.052 (2)	0.070 (2)	−0.0119 (14)	0.0044 (15)	−0.0304 (18)

Fe1—N20	1.957 (2)	C36—C37	1.508 (4)
Fe1—N10	1.959 (2)	C37—H37A	0.9800
Fe1—N60	1.963 (2)	C37—H37B	0.9800
Fe1—N30	1.965 (2)	C37—H37C	0.9800
Fe1—N50	1.967 (2)	C41—C45	1.411 (4)
Fe1—N40	1.968 (2)	C42—C43	1.399 (4)
N10—C12	1.334 (3)	C42—H42	0.9500
N10—C11	1.372 (3)	C43—C44	1.361 (4)
N20—C22	1.339 (3)	C43—H43	0.9500
N20—C21	1.368 (3)	C44—C45	1.406 (4)
N30—C32	1.339 (3)	C44—H44	0.9500
N30—C31	1.365 (3)	C45—C46	1.443 (4)
N40—C42	1.331 (3)	C46—C47	1.510 (4)
N40—C41	1.359 (3)	C47—H47A	0.9800
N50—C52	1.335 (3)	C47—H47B	0.9800
N50—C51	1.365 (3)	C47—H47C	0.9800
N60—C62	1.337 (3)	C51—C55	1.404 (4)
N60—C61	1.369 (3)	C51—C61	1.420 (4)
C11—C15	1.394 (4)	C52—C53	1.383 (4)
C11—C21	1.423 (3)	C52—H52	0.9500
C12—C13	1.393 (4)	C53—C54	1.369 (4)
C12—H12	0.9500	C53—H53	0.9500
C13—C14	1.366 (4)	C54—C55	1.408 (4)
C13—H13	0.9500	C54—H54	0.9500
C14—C15	1.406 (4)	C55—C56	1.450 (4)
C14—H14	0.9500	C56—C66	1.369 (4)
C15—C16	1.454 (4)	C56—C57	1.511 (4)
C16—C26	1.371 (4)	C57—H57A	0.9800
C16—C17	1.507 (4)	C57—H57B	0.9800
C17—H17A	0.9800	C57—H57C	0.9800
C17—H17B	0.9800	C61—C65	1.399 (4)
C17—H17C	0.9800	C62—C63	1.394 (4)
C21—C25	1.394 (4)	C62—H62	0.9500
C22—C23	1.392 (4)	C63—C64	1.367 (4)
C22—H22	0.9500	C63—H63	0.9500
C23—C24	1.360 (4)	C64—C65	1.413 (4)
C23—H23	0.9500	C64—H64	0.9500
C24—C25	1.419 (4)	C65—C66	1.449 (4)
C24—H24	0.9500	C66—C67	1.501 (4)
C25—C26	1.443 (4)	C67—H67A	0.9800
C26—C27	1.506 (4)	C67—H67B	0.9800
C27—H27A	0.9800	C67—H67C	0.9800
C27—H27B	0.9800	C1—C4	1.397 (4)
C27—H27C	0.9800	C1—C3	1.402 (5)
C31—C35	1.398 (4)	C1—C2	1.411 (5)
C31—C41	1.419 (4)	C2—N2	1.155 (5)
C32—C33	1.394 (4)	C3—N3	1.156 (4)
C32—H32	0.9500	C4—N4	1.155 (4)
C33—C34	1.363 (4)	C5—C7	1.398 (4)
C33—H33	0.9500	C5—C8	1.403 (5)
C34—C35	1.411 (4)	C5—C6	1.413 (5)
C34—H34	0.9500	C6—N6	1.151 (4)
C35—C36	1.453 (4)	C7—N7	1.157 (4)
C36—C46	1.367 (4)	C8—N8	1.157 (4)
N20—Fe1—N10	82.89 (9)	C34—C35—C36	124.8 (3)
N20—Fe1—N60	94.50 (9)	C46—C36—C35	120.5 (3)
N10—Fe1—N60	89.17 (9)	C46—C36—C37	123.2 (3)
N20—Fe1—N30	89.92 (9)	C35—C36—C37	116.3 (3)
N10—Fe1—N30	95.52 (9)	C36—C37—H37A	109.5
N60—Fe1—N30	173.92 (9)	C36—C37—H37B	109.5
N20—Fe1—N50	176.49 (9)	H37A—C37—H37B	109.5
N10—Fe1—N50	94.93 (9)	C36—C37—H37C	109.5
N60—Fe1—N50	82.70 (9)	H37A—C37—H37C	109.5
N30—Fe1—N50	93.03 (9)	H37B—C37—H37C	109.5
N20—Fe1—N40	94.31 (9)	N40—C41—C45	124.1 (2)
N10—Fe1—N40	176.56 (9)	N40—C41—C31	115.8 (2)
N60—Fe1—N40	93.05 (9)	C45—C41—C31	120.1 (2)
N30—Fe1—N40	82.45 (9)	N40—C42—C43	121.7 (3)
N50—Fe1—N40	87.97 (9)	N40—C42—H42	119.1
C12—N10—C11	117.2 (2)	C43—C42—H42	119.1
C12—N10—Fe1	129.55 (19)	C44—C43—C42	120.6 (3)
C11—N10—Fe1	113.15 (15)	C44—C43—H43	119.7
C22—N20—C21	117.6 (2)	C42—C43—H43	119.7
C22—N20—Fe1	129.00 (19)	C43—C44—C45	119.8 (3)
C21—N20—Fe1	113.43 (16)	C43—C44—H44	120.1
C32—N30—C31	117.4 (2)	C45—C44—H44	120.1
C32—N30—Fe1	129.23 (19)	C44—C45—C41	115.9 (2)
C31—N30—Fe1	113.32 (17)	C44—C45—C46	124.7 (3)
C42—N40—C41	117.8 (2)	C41—C45—C46	119.3 (3)
C42—N40—Fe1	129.02 (18)	C36—C46—C45	120.4 (3)
C41—N40—Fe1	113.08 (17)	C36—C46—C47	122.3 (3)
C52—N50—C51	117.3 (2)	C45—C46—C47	117.4 (3)
C52—N50—Fe1	129.58 (19)	C46—C47—H47A	109.5
C51—N50—Fe1	112.98 (17)	C46—C47—H47B	109.5
C62—N60—C61	117.4 (2)	H47A—C47—H47B	109.5
C62—N60—Fe1	129.68 (19)	C46—C47—H47C	109.5
C61—N60—Fe1	112.91 (17)	H47A—C47—H47C	109.5
N10—C11—C15	124.3 (2)	H47B—C47—H47C	109.5
N10—C11—C21	115.3 (2)	N50—C51—C55	124.1 (2)
C15—C11—C21	120.5 (2)	N50—C51—C61	115.4 (2)
N10—C12—C13	122.2 (3)	C55—C51—C61	120.5 (2)
N10—C12—H12	118.9	N50—C52—C53	122.5 (3)
C13—C12—H12	118.9	N50—C52—H52	118.7
C14—C13—C12	120.2 (2)	C53—C52—H52	118.7
C14—C13—H13	119.9	C54—C53—C52	120.3 (3)
C12—C13—H13	119.9	C54—C53—H53	119.8
C13—C14—C15	119.9 (2)	C52—C53—H53	119.8
C13—C14—H14	120.1	C53—C54—C55	119.7 (3)
C15—C14—H14	120.1	C53—C54—H54	120.2
C11—C15—C14	116.3 (3)	C55—C54—H54	120.2
C11—C15—C16	119.0 (2)	C51—C55—C54	116.1 (3)
C14—C15—C16	124.8 (2)	C51—C55—C56	119.0 (2)
C26—C16—C15	120.5 (2)	C54—C55—C56	124.9 (3)
C26—C16—C17	122.1 (3)	C66—C56—C55	120.5 (3)
C15—C16—C17	117.4 (2)	C66—C56—C57	122.9 (3)
C16—C17—H17A	109.5	C55—C56—C57	116.7 (3)
C16—C17—H17B	109.5	C56—C57—H57A	109.5
H17A—C17—H17B	109.5	C56—C57—H57B	109.5
C16—C17—H17C	109.5	H57A—C57—H57B	109.5
H17A—C17—H17C	109.5	C56—C57—H57C	109.5
H17B—C17—H17C	109.5	H57A—C57—H57C	109.5
N20—C21—C25	124.5 (2)	H57B—C57—H57C	109.5
N20—C21—C11	115.2 (2)	N60—C61—C65	124.4 (2)
C25—C21—C11	120.3 (2)	N60—C61—C51	115.6 (2)
N20—C22—C23	121.8 (3)	C65—C61—C51	120.1 (2)
N20—C22—H22	119.1	N60—C62—C63	122.0 (3)
C23—C22—H22	119.1	N60—C62—H62	119.0
C24—C23—C22	120.5 (2)	C63—C62—H62	119.0
C24—C23—H23	119.8	C64—C63—C62	120.4 (3)
C22—C23—H23	119.8	C64—C63—H63	119.8
C23—C24—C25	120.0 (3)	C62—C63—H63	119.8
C23—C24—H24	120.0	C63—C64—C65	119.7 (3)
C25—C24—H24	120.0	C63—C64—H64	120.1
C21—C25—C24	115.7 (2)	C65—C64—H64	120.1
C21—C25—C26	119.6 (2)	C61—C65—C64	116.1 (3)
C24—C25—C26	124.7 (3)	C61—C65—C66	119.5 (2)
C16—C26—C25	120.2 (3)	C64—C65—C66	124.4 (3)
C16—C26—C27	122.8 (3)	C56—C66—C65	120.3 (3)
C25—C26—C27	117.1 (2)	C56—C66—C67	123.4 (3)
C26—C27—H27A	109.5	C65—C66—C67	116.3 (3)
C26—C27—H27B	109.5	C66—C67—H67A	109.5
H27A—C27—H27B	109.5	C66—C67—H67B	109.5
C26—C27—H27C	109.5	H67A—C67—H67B	109.5
H27A—C27—H27C	109.5	C66—C67—H67C	109.5
H27B—C27—H27C	109.5	H67A—C67—H67C	109.5
N30—C31—C35	124.3 (3)	H67B—C67—H67C	109.5
N30—C31—C41	115.2 (2)	C4—C1—C3	119.6 (3)
C35—C31—C41	120.5 (2)	C4—C1—C2	119.9 (3)
N30—C32—C33	121.9 (3)	C3—C1—C2	120.4 (3)
N30—C32—H32	119.0	N2—C2—C1	179.3 (4)
C33—C32—H32	119.0	N3—C3—C1	178.1 (4)
C34—C33—C32	120.4 (3)	N4—C4—C1	179.2 (4)
C34—C33—H33	119.8	C7—C5—C8	120.0 (3)
C32—C33—H33	119.8	C7—C5—C6	119.8 (3)
C33—C34—C35	119.8 (3)	C8—C5—C6	120.2 (3)
C33—C34—H34	120.1	N6—C6—C5	179.5 (4)
C35—C34—H34	120.1	N7—C7—C5	178.3 (4)
C31—C35—C34	116.1 (3)	N8—C8—C5	179.3 (4)
C31—C35—C36	119.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C52—H52···N30	0.95	2.59	3.070 (3)	112
C22—H22···N40	0.95	2.59	3.089 (4)	113
C32—H32···N8	0.95	2.43	3.266 (4)	146
C42—H42···N60	0.95	2.57	3.056 (3)	112
C22—H22···N6i	0.95	2.54	3.271 (4)	134
C12—H12···N2ii	0.95	2.55	3.352 (4)	142
C62—H62···N3iii	0.95	2.51	3.266 (4)	137
C44—H44···N7iv	0.95	2.59	3.312 (4)	133

Table 1

Selected bond lengths (Å)

Fe1—N20	1.957 (2)
Fe1—N10	1.959 (2)
Fe1—N60	1.963 (2)
Fe1—N30	1.965 (2)
Fe1—N50	1.967 (2)
Fe1—N40	1.968 (2)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C52—H52⋯N30	0.95	2.59	3.070 (3)	112
C22—H22⋯N40	0.95	2.59	3.089 (4)	113
C32—H32⋯N8	0.95	2.43	3.266 (4)	146
C42—H42⋯N60	0.95	2.57	3.056 (3)	112
C22—H22⋯N6i	0.95	2.54	3.271 (4)	134
C12—H12⋯N2ii	0.95	2.55	3.352 (4)	142
C62—H62⋯N3iii	0.95	2.51	3.266 (4)	137
C44—H44⋯N7iv	0.95	2.59	3.312 (4)	133

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .