[2,2'-(2,6,9,13-Tetra-azatetra-decane-1,14-di-yl)diphenolato]iron(III) iodide.

The title Fe(III) complex, [Fe(C(22)H(32)N(4)O(2))]I, contains a six-coordinate FeN(4)O(2) cation in which the ligand is a reduced Schiff base resulting from the NaBH(4) reduction of the condensation product between salicylaldehyde and 1,5,8,12-tetra-azadodecane. In spite of the increased flexibility of the saturated backbone of the ligand compared to the Schiff base from which it was synthesized, the complex adopts a cis-FeN(4)O(2) conformation for the phenolic O-atom donors, which contrasts with the trans conformation adopted by the analogous ClO(4) (-) salt [Yisgedu et al. (2009 ▶). J. Chem. Crystallogr.39, 315-319]. In addition to extensive N-H⋯I hydrogen bonding between the amine H atoms and the anion there is a weak C-H⋯I inter-action.

Related literature

For early literature related to hexa­dentate ligands, see: Dwyer & Lions (1947 ▶); Das Sarma & Bailar (1955 ▶). For geometric changes from cis to trans, see: Bera et al. (2005 ▶); Boinnard et al. (1994 ▶); Dorbes et al. (2005 ▶); Floquet et al. (2004 ▶); Hayami et al. (1997 ▶); Ito et al. (1983 ▶); Maeda et al. (1991 ▶); McPartlin et al. (1978 ▶); Nishida et al. (1987 ▶); Salmon et al. (1999 ▶); Sinn et al. (1978 ▶). For complexes of reduced Schiff bases, see: Harpstrite et al. (2003 ▶). For the analogous ClO4 − salt, see: Yisgedu et al. (2009 ▶).

Experimental

Crystal data

[Fe(C22H32N4O2)]I

M = 567.27

Orthorhombic,

a = 9.3958 (1) Å

b = 13.0509 (1) Å

c = 19.4047 (3) Å

V = 2379.48 (5) Å3

Z = 4

Mo Kα radiation

μ = 1.96 mm−1

T = 200 K

0.51 × 0.47 × 0.39 mm

Data collection

Oxford Diffraction Gemini R diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T min = 0.428, T max = 0.466

43714 measured reflections

9836 independent reflections

7672 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.066

S = 0.94

9836 reflections

271 parameters

H-atom parameters constrained

Δρmax = 1.32 e Å−3

Δρmin = −0.45 e Å−3

Absolute structure: Flack (1983 ▶), 4113 Friedel pairs

Flack parameter: −0.018 (11)

Data collection: CrysAlis CCD (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810018787/zl2278sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810018787/zl2278Isup2.hkl

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

[Fe(C22H32N4O2)]I	F(000) = 1148
Mr = 567.27	Dx = 1.583 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 18399 reflections
a = 9.3958 (1) Å	θ = 4.6–34.7°
b = 13.0509 (1) Å	µ = 1.96 mm−1
c = 19.4047 (3) Å	T = 200 K
V = 2379.48 (5) Å3	Chunk, dark brown-red
Z = 4	0.51 × 0.47 × 0.39 mm

Oxford Diffraction Gemini R diffractometer	9836 independent reflections
Radiation source: fine-focus sealed tube	7672 reflections with I > 2σ(I)
graphite	Rint = 0.036
Detector resolution: 10.5081 pixels mm-1	θmax = 34.8°, θmin = 4.7°
φ and ω scans	h = −14→14
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	k = −20→20
Tmin = 0.428, Tmax = 0.466	l = −30→31
43714 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.033	H-atom parameters constrained
wR(F2) = 0.066	w = 1/[σ2(Fo2) + (0.0354P)2] where P = (Fo2 + 2Fc2)/3
S = 0.94	(Δ/σ)max = 0.001
9836 reflections	Δρmax = 1.32 e Å−3
271 parameters	Δρmin = −0.45 e Å−3
0 restraints	Absolute structure: Flack (1983), 4113 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.018 (11)

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. 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
I	0.773383 (17)	−0.160323 (12)	0.264361 (9)	0.04200 (5)
Fe	0.82534 (3)	0.15269 (2)	0.131418 (12)	0.01814 (5)
O1A	0.79828 (16)	0.08061 (11)	0.04737 (7)	0.0277 (3)
O1B	0.71110 (15)	0.26909 (10)	0.11418 (7)	0.0254 (3)
N1A	0.64230 (16)	0.07176 (12)	0.17734 (8)	0.0203 (3)
H1AA	0.6763	0.0195	0.2054	0.024*
N2A	0.86624 (18)	0.20378 (12)	0.23797 (9)	0.0247 (3)
H2AA	0.9344	0.2551	0.2342	0.030*
N1B	1.01197 (16)	0.23195 (12)	0.09118 (8)	0.0199 (3)
H1BA	1.0639	0.2579	0.1281	0.024*
N2B	0.97740 (18)	0.03588 (13)	0.16943 (9)	0.0250 (3)
H2BA	0.9218	−0.0207	0.1805	0.030*
C1A	0.7469 (2)	−0.01336 (15)	0.03747 (10)	0.0243 (4)
C2A	0.8057 (3)	−0.07758 (19)	−0.01269 (12)	0.0385 (5)
H2AB	0.8846	−0.0551	−0.0393	0.046*
C3A	0.7485 (3)	−0.17422 (19)	−0.02343 (14)	0.0450 (6)
H3AA	0.7890	−0.2178	−0.0574	0.054*
C4A	0.6331 (3)	−0.20817 (18)	0.01467 (13)	0.0447 (6)
H4AA	0.5944	−0.2744	0.0068	0.054*
C5A	0.5753 (3)	−0.14535 (17)	0.06366 (11)	0.0352 (5)
H5AA	0.4969	−0.1691	0.0902	0.042*
C6A	0.6286 (2)	−0.04757 (15)	0.07560 (10)	0.0253 (4)
C7A	0.5530 (2)	0.02586 (16)	0.12218 (10)	0.0250 (4)
H7AA	0.5130	0.0819	0.0938	0.030*
H7AB	0.4722	−0.0104	0.1440	0.030*
C8A	0.5495 (2)	0.14035 (17)	0.21940 (11)	0.0293 (4)
H8AA	0.4621	0.1025	0.2322	0.035*
H8AB	0.5206	0.1996	0.1908	0.035*
C9A	0.6201 (3)	0.17974 (17)	0.28458 (11)	0.0327 (5)
H9AA	0.5473	0.2158	0.3124	0.039*
H9AB	0.6530	0.1201	0.3117	0.039*
C10A	0.7452 (2)	0.25153 (15)	0.27417 (10)	0.0305 (4)
H10A	0.7129	0.3118	0.2475	0.037*
H10B	0.7780	0.2762	0.3197	0.037*
C11A	0.9351 (3)	0.12131 (18)	0.27913 (12)	0.0338 (5)
H11A	0.8624	0.0716	0.2948	0.041*
H11B	0.9814	0.1512	0.3203	0.041*
C1B	0.74548 (19)	0.36819 (14)	0.10896 (9)	0.0226 (4)
C2B	0.6501 (2)	0.44332 (17)	0.13160 (11)	0.0310 (4)
H2BB	0.5632	0.4239	0.1529	0.037*
C3B	0.6827 (3)	0.54589 (17)	0.12298 (12)	0.0352 (5)
H3BA	0.6161	0.5965	0.1371	0.042*
C4B	0.8109 (2)	0.57591 (16)	0.09400 (12)	0.0329 (5)
H4BA	0.8326	0.6466	0.0887	0.040*
C5B	0.9073 (2)	0.50167 (15)	0.07286 (11)	0.0273 (4)
H5BA	0.9963	0.5219	0.0540	0.033*
C6B	0.8749 (2)	0.39720 (14)	0.07890 (10)	0.0216 (4)
C7B	0.9688 (2)	0.31914 (15)	0.04574 (10)	0.0247 (4)
H7BA	1.0560	0.3539	0.0291	0.030*
H7BB	0.9189	0.2910	0.0050	0.030*
C8B	1.1072 (2)	0.16359 (18)	0.04945 (10)	0.0285 (4)
H8BA	1.1804	0.2063	0.0266	0.034*
H8BB	1.0498	0.1306	0.0129	0.034*
C9B	1.1806 (2)	0.08143 (18)	0.09064 (12)	0.0332 (5)
H9BA	1.2307	0.1142	0.1297	0.040*
H9BB	1.2534	0.0487	0.0611	0.040*
C10B	1.0824 (2)	−0.00223 (16)	0.11913 (12)	0.0315 (5)
H10C	1.0311	−0.0347	0.0803	0.038*
H10D	1.1413	−0.0557	0.1414	0.038*
C11B	1.0443 (2)	0.06764 (17)	0.23547 (12)	0.0322 (4)
H11C	1.1252	0.1143	0.2262	0.039*
H11D	1.0810	0.0067	0.2601	0.039*

	U11	U22	U33	U12	U13	U23
I	0.03535 (8)	0.03358 (7)	0.05708 (10)	−0.00127 (7)	−0.00778 (7)	0.01797 (7)
Fe	0.01560 (10)	0.02019 (11)	0.01862 (11)	0.00004 (10)	0.00055 (9)	0.00102 (10)
O1A	0.0264 (8)	0.0351 (7)	0.0216 (7)	−0.0061 (6)	0.0031 (5)	−0.0040 (5)
O1B	0.0174 (6)	0.0267 (6)	0.0321 (7)	0.0016 (5)	0.0029 (5)	0.0081 (5)
N1A	0.0186 (7)	0.0219 (7)	0.0203 (7)	−0.0002 (6)	0.0024 (6)	0.0010 (6)
N2A	0.0264 (8)	0.0245 (7)	0.0233 (8)	−0.0040 (6)	−0.0009 (7)	0.0012 (6)
N1B	0.0131 (7)	0.0245 (7)	0.0219 (7)	0.0000 (6)	0.0008 (6)	0.0021 (6)
N2B	0.0220 (8)	0.0217 (7)	0.0314 (9)	−0.0003 (6)	−0.0027 (7)	0.0021 (6)
C1A	0.0229 (10)	0.0284 (9)	0.0215 (8)	0.0018 (7)	−0.0041 (7)	−0.0035 (7)
C2A	0.0375 (13)	0.0475 (13)	0.0305 (11)	0.0073 (10)	−0.0024 (9)	−0.0118 (9)
C3A	0.0488 (16)	0.0396 (12)	0.0466 (13)	0.0141 (11)	−0.0102 (11)	−0.0189 (10)
C4A	0.0655 (18)	0.0248 (10)	0.0439 (14)	0.0010 (11)	−0.0180 (13)	−0.0027 (9)
C5A	0.0441 (13)	0.0296 (11)	0.0318 (11)	−0.0085 (10)	−0.0093 (9)	0.0050 (9)
C6A	0.0268 (10)	0.0275 (9)	0.0217 (9)	−0.0018 (8)	−0.0071 (7)	0.0017 (7)
C7A	0.0169 (8)	0.0316 (9)	0.0264 (10)	−0.0027 (7)	0.0000 (7)	0.0002 (7)
C8A	0.0231 (9)	0.0333 (11)	0.0314 (10)	0.0005 (8)	0.0099 (7)	−0.0013 (8)
C9A	0.0370 (12)	0.0345 (11)	0.0267 (10)	−0.0021 (9)	0.0115 (8)	−0.0040 (8)
C10A	0.0400 (13)	0.0268 (9)	0.0246 (9)	−0.0037 (8)	0.0064 (8)	−0.0060 (7)
C11A	0.0376 (12)	0.0371 (11)	0.0267 (11)	−0.0007 (9)	−0.0071 (9)	0.0059 (8)
C1B	0.0217 (10)	0.0257 (8)	0.0204 (8)	0.0031 (6)	−0.0008 (6)	0.0043 (6)
C2B	0.0251 (10)	0.0347 (10)	0.0331 (10)	0.0072 (8)	0.0044 (9)	0.0054 (9)
C3B	0.0404 (12)	0.0304 (10)	0.0350 (12)	0.0141 (9)	−0.0024 (10)	−0.0017 (9)
C4B	0.0372 (13)	0.0243 (9)	0.0373 (12)	0.0035 (9)	−0.0072 (9)	0.0026 (8)
C5B	0.0262 (10)	0.0298 (10)	0.0260 (10)	−0.0022 (8)	−0.0030 (8)	0.0049 (8)
C6B	0.0206 (9)	0.0242 (8)	0.0201 (9)	0.0007 (7)	−0.0009 (7)	0.0041 (7)
C7B	0.0211 (9)	0.0297 (10)	0.0233 (9)	0.0015 (7)	0.0028 (7)	0.0083 (7)
C8B	0.0195 (8)	0.0346 (10)	0.0315 (10)	0.0057 (9)	0.0086 (7)	0.0007 (9)
C9B	0.0188 (9)	0.0382 (11)	0.0427 (13)	0.0100 (9)	0.0023 (9)	−0.0006 (9)
C10B	0.0285 (11)	0.0273 (10)	0.0388 (12)	0.0089 (8)	−0.0002 (9)	0.0005 (8)
C11B	0.0325 (11)	0.0343 (10)	0.0296 (11)	0.0014 (8)	−0.0115 (9)	0.0047 (9)

Fe—O1B	1.8898 (13)	C8A—H8AA	0.9900
Fe—O1A	1.8999 (14)	C8A—H8AB	0.9900
Fe—N1B	2.1805 (15)	C9A—C10A	1.517 (3)
Fe—N1A	2.2062 (15)	C9A—H9AA	0.9900
Fe—N2A	2.2062 (17)	C9A—H9AB	0.9900
Fe—N2B	2.2158 (17)	C10A—H10A	0.9900
O1A—C1A	1.332 (2)	C10A—H10B	0.9900
O1B—C1B	1.337 (2)	C11A—C11B	1.504 (3)
N1A—C7A	1.486 (2)	C11A—H11A	0.9900
N1A—C8A	1.493 (2)	C11A—H11B	0.9900
N1A—H1AA	0.9300	C1B—C2B	1.399 (3)
N2A—C10A	1.475 (3)	C1B—C6B	1.401 (3)
N2A—C11A	1.488 (3)	C2B—C3B	1.383 (3)
N2A—H2AA	0.9300	C2B—H2BB	0.9500
N1B—C7B	1.496 (2)	C3B—C4B	1.386 (3)
N1B—C8B	1.501 (2)	C3B—H3BA	0.9500
N1B—H1BA	0.9300	C4B—C5B	1.388 (3)
N2B—C10B	1.474 (3)	C4B—H4BA	0.9500
N2B—C11B	1.486 (3)	C5B—C6B	1.402 (3)
N2B—H2BA	0.9300	C5B—H5BA	0.9500
C1A—C2A	1.398 (3)	C6B—C7B	1.493 (3)
C1A—C6A	1.408 (3)	C7B—H7BA	0.9900
C2A—C3A	1.387 (3)	C7B—H7BB	0.9900
C2A—H2AB	0.9500	C8B—C9B	1.505 (3)
C3A—C4A	1.385 (4)	C8B—H8BA	0.9900
C3A—H3AA	0.9500	C8B—H8BB	0.9900
C4A—C5A	1.368 (4)	C9B—C10B	1.533 (3)
C4A—H4AA	0.9500	C9B—H9BA	0.9900
C5A—C6A	1.390 (3)	C9B—H9BB	0.9900
C5A—H5AA	0.9500	C10B—H10C	0.9900
C6A—C7A	1.497 (3)	C10B—H10D	0.9900
C7A—H7AA	0.9900	C11B—H11C	0.9900
C7A—H7AB	0.9900	C11B—H11D	0.9900
C8A—C9A	1.518 (3)
O1B—Fe—O1A	99.79 (6)	C9A—C8A—H8AB	108.8
O1B—Fe—N1B	90.69 (6)	H8AA—C8A—H8AB	107.7
O1A—Fe—N1B	92.02 (6)	C10A—C9A—C8A	115.90 (17)
O1B—Fe—N1A	90.78 (6)	C10A—C9A—H9AA	108.3
O1A—Fe—N1A	90.31 (6)	C8A—C9A—H9AA	108.3
N1B—Fe—N1A	177.01 (6)	C10A—C9A—H9AB	108.3
O1B—Fe—N2A	91.25 (6)	C8A—C9A—H9AB	108.3
O1A—Fe—N2A	167.81 (6)	H9AA—C9A—H9AB	107.4
N1B—Fe—N2A	92.99 (6)	N2A—C10A—C9A	113.59 (16)
N1A—Fe—N2A	84.37 (6)	N2A—C10A—H10A	108.8
O1B—Fe—N2B	168.01 (6)	C9A—C10A—H10A	108.8
O1A—Fe—N2B	91.80 (6)	N2A—C10A—H10B	108.8
N1B—Fe—N2B	85.82 (6)	C9A—C10A—H10B	108.8
N1A—Fe—N2B	92.22 (6)	H10A—C10A—H10B	107.7
N2A—Fe—N2B	77.50 (6)	N2A—C11A—C11B	109.34 (17)
C1A—O1A—Fe	128.92 (12)	N2A—C11A—H11A	109.8
C1B—O1B—Fe	130.83 (12)	C11B—C11A—H11A	109.8
C7A—N1A—C8A	107.79 (15)	N2A—C11A—H11B	109.8
C7A—N1A—Fe	110.01 (11)	C11B—C11A—H11B	109.8
C8A—N1A—Fe	112.91 (12)	H11A—C11A—H11B	108.3
C7A—N1A—H1AA	108.7	O1B—C1B—C2B	119.97 (17)
C8A—N1A—H1AA	108.7	O1B—C1B—C6B	120.18 (16)
Fe—N1A—H1AA	108.7	C2B—C1B—C6B	119.82 (17)
C10A—N2A—C11A	112.66 (17)	C3B—C2B—C1B	119.9 (2)
C10A—N2A—Fe	116.09 (13)	C3B—C2B—H2BB	120.0
C11A—N2A—Fe	111.11 (13)	C1B—C2B—H2BB	120.0
C10A—N2A—H2AA	105.3	C2B—C3B—C4B	121.0 (2)
C11A—N2A—H2AA	105.3	C2B—C3B—H3BA	119.5
Fe—N2A—H2AA	105.3	C4B—C3B—H3BA	119.5
C7B—N1B—C8B	107.20 (15)	C3B—C4B—C5B	119.31 (19)
C7B—N1B—Fe	110.74 (11)	C3B—C4B—H4BA	120.3
C8B—N1B—Fe	112.99 (12)	C5B—C4B—H4BA	120.3
C7B—N1B—H1BA	108.6	C4B—C5B—C6B	120.9 (2)
C8B—N1B—H1BA	108.6	C4B—C5B—H5BA	119.6
Fe—N1B—H1BA	108.6	C6B—C5B—H5BA	119.6
C10B—N2B—C11B	112.46 (17)	C1B—C6B—C5B	119.06 (18)
C10B—N2B—Fe	116.31 (13)	C1B—C6B—C7B	120.53 (17)
C11B—N2B—Fe	111.58 (12)	C5B—C6B—C7B	119.96 (18)
C10B—N2B—H2BA	105.1	C6B—C7B—N1B	115.16 (15)
C11B—N2B—H2BA	105.1	C6B—C7B—H7BA	108.5
Fe—N2B—H2BA	105.1	N1B—C7B—H7BA	108.5
O1A—C1A—C2A	120.62 (19)	C6B—C7B—H7BB	108.5
O1A—C1A—C6A	120.15 (17)	N1B—C7B—H7BB	108.5
C2A—C1A—C6A	119.18 (19)	H7BA—C7B—H7BB	107.5
C3A—C2A—C1A	119.8 (2)	N1B—C8B—C9B	114.22 (16)
C3A—C2A—H2AB	120.1	N1B—C8B—H8BA	108.7
C1A—C2A—H2AB	120.1	C9B—C8B—H8BA	108.7
C4A—C3A—C2A	120.9 (2)	N1B—C8B—H8BB	108.7
C4A—C3A—H3AA	119.5	C9B—C8B—H8BB	108.7
C2A—C3A—H3AA	119.5	H8BA—C8B—H8BB	107.6
C5A—C4A—C3A	119.3 (2)	C8B—C9B—C10B	115.07 (18)
C5A—C4A—H4AA	120.3	C8B—C9B—H9BA	108.5
C3A—C4A—H4AA	120.3	C10B—C9B—H9BA	108.5
C4A—C5A—C6A	121.5 (2)	C8B—C9B—H9BB	108.5
C4A—C5A—H5AA	119.2	C10B—C9B—H9BB	108.5
C6A—C5A—H5AA	119.2	H9BA—C9B—H9BB	107.5
C5A—C6A—C1A	119.21 (19)	N2B—C10B—C9B	113.66 (17)
C5A—C6A—C7A	121.14 (19)	N2B—C10B—H10C	108.8
C1A—C6A—C7A	119.29 (17)	C9B—C10B—H10C	108.8
N1A—C7A—C6A	115.14 (16)	N2B—C10B—H10D	108.8
N1A—C7A—H7AA	108.5	C9B—C10B—H10D	108.8
C6A—C7A—H7AA	108.5	H10C—C10B—H10D	107.7
N1A—C7A—H7AB	108.5	N2B—C11B—C11A	109.10 (17)
C6A—C7A—H7AB	108.5	N2B—C11B—H11C	109.9
H7AA—C7A—H7AB	107.5	C11A—C11B—H11C	109.9
N1A—C8A—C9A	113.79 (17)	N2B—C11B—H11D	109.9
N1A—C8A—H8AA	108.8	C11A—C11B—H11D	109.9
C9A—C8A—H8AA	108.8	H11C—C11B—H11D	108.3
N1A—C8A—H8AB	108.8
O1B—Fe—O1A—C1A	−121.63 (16)	C6A—C1A—C2A—C3A	−1.0 (3)
N1B—Fe—O1A—C1A	147.32 (16)	C1A—C2A—C3A—C4A	0.3 (4)
N1A—Fe—O1A—C1A	−30.79 (16)	C2A—C3A—C4A—C5A	−0.2 (4)
N2A—Fe—O1A—C1A	33.1 (4)	C3A—C4A—C5A—C6A	0.8 (4)
N2B—Fe—O1A—C1A	61.45 (16)	C4A—C5A—C6A—C1A	−1.5 (3)
O1A—Fe—O1B—C1B	−116.70 (15)	C4A—C5A—C6A—C7A	171.5 (2)
N1B—Fe—O1B—C1B	−24.54 (15)	O1A—C1A—C6A—C5A	178.97 (18)
N1A—Fe—O1B—C1B	152.85 (15)	C2A—C1A—C6A—C5A	1.6 (3)
N2A—Fe—O1B—C1B	68.47 (16)	O1A—C1A—C6A—C7A	5.8 (3)
N2B—Fe—O1B—C1B	48.3 (4)	C2A—C1A—C6A—C7A	−171.55 (19)
O1B—Fe—N1A—C7A	82.12 (12)	C8A—N1A—C7A—C6A	−178.68 (16)
O1A—Fe—N1A—C7A	−17.68 (12)	Fe—N1A—C7A—C6A	57.82 (18)
N2A—Fe—N1A—C7A	173.30 (13)	C5A—C6A—C7A—N1A	127.69 (19)
N2B—Fe—N1A—C7A	−109.49 (12)	C1A—C6A—C7A—N1A	−59.3 (2)
O1B—Fe—N1A—C8A	−38.34 (13)	C7A—N1A—C8A—C9A	170.82 (17)
O1A—Fe—N1A—C8A	−138.14 (13)	Fe—N1A—C8A—C9A	−67.46 (19)
N2A—Fe—N1A—C8A	52.85 (13)	N1A—C8A—C9A—C10A	66.2 (2)
N2B—Fe—N1A—C8A	130.06 (13)	C11A—N2A—C10A—C9A	−66.6 (2)
O1B—Fe—N2A—C10A	38.47 (13)	Fe—N2A—C10A—C9A	63.1 (2)
O1A—Fe—N2A—C10A	−116.6 (3)	C8A—C9A—C10A—N2A	−62.7 (3)
N1B—Fe—N2A—C10A	129.23 (13)	C10A—N2A—C11A—C11B	172.73 (16)
N1A—Fe—N2A—C10A	−52.18 (13)	Fe—N2A—C11A—C11B	40.5 (2)
N2B—Fe—N2A—C10A	−145.72 (14)	Fe—O1B—C1B—C2B	−146.23 (16)
O1B—Fe—N2A—C11A	168.93 (14)	Fe—O1B—C1B—C6B	35.7 (2)
O1A—Fe—N2A—C11A	13.8 (4)	O1B—C1B—C2B—C3B	−176.72 (19)
N1B—Fe—N2A—C11A	−100.31 (14)	C6B—C1B—C2B—C3B	1.3 (3)
N1A—Fe—N2A—C11A	78.27 (14)	C1B—C2B—C3B—C4B	−2.0 (3)
N2B—Fe—N2A—C11A	−15.27 (14)	C2B—C3B—C4B—C5B	0.6 (3)
O1B—Fe—N1B—C7B	−20.81 (13)	C3B—C4B—C5B—C6B	1.6 (3)
O1A—Fe—N1B—C7B	79.02 (13)	O1B—C1B—C6B—C5B	178.81 (17)
N2A—Fe—N1B—C7B	−112.10 (12)	C2B—C1B—C6B—C5B	0.8 (3)
N2B—Fe—N1B—C7B	170.67 (13)	O1B—C1B—C6B—C7B	6.5 (3)
O1B—Fe—N1B—C8B	−141.09 (13)	C2B—C1B—C6B—C7B	−171.54 (18)
O1A—Fe—N1B—C8B	−41.26 (13)	C4B—C5B—C6B—C1B	−2.2 (3)
N2A—Fe—N1B—C8B	127.62 (12)	C4B—C5B—C6B—C7B	170.12 (19)
N2B—Fe—N1B—C8B	50.39 (13)	C1B—C6B—C7B—N1B	−56.4 (2)
O1B—Fe—N2B—C10B	−122.7 (3)	C5B—C6B—C7B—N1B	131.38 (19)
O1A—Fe—N2B—C10B	42.58 (14)	C8B—N1B—C7B—C6B	−178.95 (16)
N1B—Fe—N2B—C10B	−49.31 (14)	Fe—N1B—C7B—C6B	57.38 (19)
N1A—Fe—N2B—C10B	132.95 (14)	C7B—N1B—C8B—C9B	170.13 (18)
N2A—Fe—N2B—C10B	−143.31 (15)	Fe—N1B—C8B—C9B	−67.59 (19)
O1B—Fe—N2B—C11B	8.1 (4)	N1B—C8B—C9B—C10B	68.4 (2)
O1A—Fe—N2B—C11B	173.41 (14)	C11B—N2B—C10B—C9B	−69.6 (2)
N1B—Fe—N2B—C11B	81.52 (14)	Fe—N2B—C10B—C9B	60.8 (2)
N1A—Fe—N2B—C11B	−96.21 (13)	C8B—C9B—C10B—N2B	−63.9 (3)
N2A—Fe—N2B—C11B	−12.48 (13)	C10B—N2B—C11B—C11A	170.70 (16)
Fe—O1A—C1A—C2A	−141.17 (18)	Fe—N2B—C11B—C11A	37.91 (19)
Fe—O1A—C1A—C6A	41.5 (2)	N2A—C11A—C11B—N2B	−51.6 (2)
O1A—C1A—C2A—C3A	−178.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1AA···I	0.93	2.77	3.6800 (16)	168
N2A—H2AA···Ii	0.93	2.96	3.8227 (17)	155
N1B—H1BA···Ii	0.93	2.80	3.7285 (16)	178
N2B—H2BA···I	0.93	2.81	3.6911 (17)	158
C11B—H11C···Ii	0.99	3.10	3.942 (2)	144

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1A—H1AA⋯I	0.93	2.77	3.6800 (16)	168
N2A—H2AA⋯Ii	0.93	2.96	3.8227 (17)	155
N1B—H1BA⋯Ii	0.93	2.80	3.7285 (16)	178
N2B—H2BA⋯I	0.93	2.81	3.6911 (17)	158
C11B—H11C⋯Ii	0.99	3.10	3.942 (2)	144

Symmetry code: (i) .