[Fe(C₁₂H₈N₃O₂)Cl₂(ROH)], with R = Me and Et

The title octahedral complexes, [bis(pyridine-2-carbonyl)­amin­ate]­di­chloro­(methanol)­iron(III), [Fe(C₁₂H₈N₃O₂)­Cl₂-(CH₄O)], and [bis­(pyri­dine-2-carbonyl)­amin­ate]­di­chloro-(ethanol)­iron(III), [Fe­(C₁₂H₈N₃O₂)Cl₂(C₂H₆O)], both crystallize in space group and have similar structures. Mono­anionic bpca^- [bis(pyridine-2-carbonyl)­amin­ate] acts as a planar tridentate ligand in both cases. Coordination bond distances are in the range typical of high-spin Fe^III complexes. Carbon-oxygen distances are typical of a C=O double bond suggesting the negative charge of the bpca^- ligand is localized on the central N atom.

S1. Comment

It is known that bpca⁻ [bis(pyridine-2-carbonyl)aminate], formed upon deprotonation of Hbpca, acts as a tridentate N-donor rigid ligand and coordinates to transition metal ions such as Fe^II and Fe^III (Wocadlo et al., 1993), Mn^II (Marcos et al., 1990), Cu^II and Zn^II (Marcos et al., 1989), and Rh^III (Paul et al., 1998). The resulting [M(bpca)₂]ⁿ⁺ complex cation contains two sets of free β-diketone groups which can coordinate to other metal ions in a chelating mode. We demonstrated that this type of complex acts as a bridging complex ligand to give multi-metal-centered complexes (Kajiwara et al., 1998). With Cu^II and Fe^III ions, this ligand also forms other types of complexes formulated as [Cu(bpca)X(H₂O)_n] (Folgado et al., 1988, 1989) and [Fe(bpca)Cl₂(H₂O)] (Wocadlo et al., 1993). The latter contains high-spin Fe^III, whereas the Fe^III ions in [Fe(bpca)₂]X are in a low-spin or medium-spin state depending on X. Such high-spin complexes can be excellent complexing ligands in the construction of multi-metal complexes with a large high-spin ground state. We report here two novel Fe^III complexes, namely [bis(pyridine-2-carbonyl)aminate]dichloro(methanol)iron(III), (I), and [bis(pyridine-2-carbonyl)aminate]dichloro(ethanol)iron(III), (II), which are promising high-spin complexing ligands.

The reaction of Hbpca in nitromethane with FeCl₃ in methanol or ethanol affords yellow crystals of (I) and (II), respectively. The molecular structures of (I) and (II) are very similar to each other except for the coordinating alcohol molecules. The hexacoordination of the Fe^III ion in each compound is achieved by three N atoms from the planar bpca⁻ ligand, two Cl ligands cis to each other and the O atom of the alcohol. Iron–ligand distances are all in the range expected for high-spin Fe^III complexes (Wocadlo et al., 1993). The O3–Fe–L angles (L = N1, N2 and N3) are significantly smaller than 90°. Atoms N1, N2, N3 and Cl1 are practically coplanar, and the Fe atom deviates by 0.203 (1) and 0.1979 (7) Å from their best mean planes in (I) and (II), respectively. The C═O distances [1.223 (3) and 1.218 (3) Å in (I), and 1.222 (2) and 1.214 (2) Å in (II)] are in the usual range for a C═O double bond (Etter et al., 1991), suggesting that the negative charge of bpca⁻ is localized mainly on the amide N atom of the O—C—N—C—O moiety.

S2. Experimental

Solutions of Hbpca (113 mg, 0.5 mmol) in nitromethane (5 ml) and FeCl₃ (81 mg, 0.05 mmol) in methyl alcohol or ethyl alcohol (5 ml) were mixed with stirring. From the resulting yellow–orange solutions, yellow compounds crystallized after a few days.

S3. Refinement

H atoms were refined and the resulting O—H and C—H dimensions are (I) O—H 0.69 (4) and C—H 0.90 (3)–1.02 (4) Å; (II) O—H 0.69 (2) and C—H 0.84 (2)–1.16 (4) Å.

Computing details

For both compounds, data collection: SMART (Bruker, 1998); cell refinement: SMART and SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: TEXSAN (Molecular Structure Corporation & Rigaku Corporation, 1998); software used to prepare material for publication: SHELXL97.

Figures

	Fig. 1. The molecular structure of (1) showing 50% probability displacement ellipsoids.
	Fig. 2. The molecular structure of (2) showing 50% probability displacement ellipsoids.

(I)

Crystal data

[Fe(C12H8N3O2)Cl2(CH4O)]	Z = 2
Mr = 385.01	F(000) = 390
Triclinic, P1	Dx = 1.696 Mg m^−3
a = 8.3695 (11) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.5208 (11) Å	Cell parameters from 2034 reflections
c = 11.7567 (16) Å	θ = 1.8–26.0°
α = 101.532 (2)°	µ = 1.37 mm^−1
β = 97.517 (2)°	T = 223 K
γ = 109.958 (3)°	Prismatic, yellow
V = 753.91 (17) Å^3	0.25 × 0.24 × 0.18 mm

Data collection

Bruker CCD area-detector diffractometer	2795 independent reflections
Radiation source: fine-focus sealed tube	2247 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.057
ω scans	θmax = 26.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→7
Tmin = 0.582, Tmax = 0.801	k = −5→10
3890 measured reflections	l = −14→14

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.090	All H-atom parameters refined
S = 0.99	w = 1/[σ^2(Fo^2) + (0.0478P)^2] where P = (Fo^2 + 2Fc^2)/3
2795 reflections	(Δ/σ)max = 0.001
247 parameters	Δρmax = 0.39 e Å^−3
0 restraints	Δρmin = −0.63 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Fe1	0.67363 (5)	0.30928 (5)	0.71699 (3)	0.02223 (14)
Cl1	0.62848 (10)	0.32589 (11)	0.52714 (6)	0.0369 (2)
Cl2	0.40061 (9)	0.11938 (10)	0.71164 (6)	0.03317 (19)
O1	0.8151 (3)	0.5097 (3)	1.08622 (16)	0.0302 (5)
O2	0.9078 (3)	0.2231 (3)	1.02267 (17)	0.0346 (5)
O3	0.9461 (3)	0.4890 (3)	0.73200 (18)	0.0271 (5)
N1	0.6293 (3)	0.5291 (3)	0.80433 (19)	0.0241 (5)
N2	0.7718 (3)	0.3386 (3)	0.89498 (18)	0.0209 (5)
N3	0.7841 (3)	0.1191 (3)	0.7087 (2)	0.0249 (5)
C1	0.5505 (4)	0.6172 (4)	0.7509 (3)	0.0308 (7)
C2	0.5200 (4)	0.7541 (4)	0.8151 (3)	0.0367 (8)
C3	0.5703 (4)	0.8007 (4)	0.9372 (3)	0.0392 (8)
C4	0.6513 (4)	0.7105 (4)	0.9932 (3)	0.0310 (7)
C5	0.6779 (3)	0.5755 (3)	0.9235 (2)	0.0229 (6)
C6	0.7636 (3)	0.4699 (3)	0.9783 (2)	0.0214 (6)
C7	0.8510 (3)	0.2302 (3)	0.9238 (2)	0.0231 (6)
C8	0.8619 (3)	0.1106 (3)	0.8139 (2)	0.0229 (6)
C9	0.9448 (4)	−0.0035 (4)	0.8204 (3)	0.0318 (7)
C10	0.9462 (4)	−0.1118 (4)	0.7174 (3)	0.0400 (8)
C11	0.8640 (5)	−0.1061 (4)	0.6100 (3)	0.0410 (8)
C12	0.7835 (4)	0.0119 (4)	0.6083 (3)	0.0329 (7)
C13	1.0563 (5)	0.4632 (6)	0.6531 (3)	0.0425 (9)
H1	0.525 (4)	0.585 (4)	0.671 (3)	0.025 (8)*
H2	0.466 (5)	0.805 (4)	0.771 (3)	0.050 (10)*
H3A	0.553 (4)	0.895 (4)	0.982 (3)	0.036 (9)*
H3B	0.992 (5)	0.516 (5)	0.790 (3)	0.049 (12)*
H4	0.682 (4)	0.736 (4)	1.076 (3)	0.034 (8)*
H9	0.997 (4)	−0.004 (4)	0.897 (3)	0.034 (9)*
H10	0.995 (5)	−0.193 (5)	0.718 (3)	0.059 (11)*
H11	0.855 (4)	−0.188 (4)	0.532 (3)	0.044 (9)*
H12	0.729 (4)	0.021 (4)	0.540 (3)	0.030 (8)*
H13A	0.993 (5)	0.413 (5)	0.574 (4)	0.059 (11)*
H13B	1.130 (5)	0.580 (5)	0.642 (3)	0.060 (12)*
H13C	1.138 (6)	0.417 (6)	0.690 (4)	0.090 (15)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe1	0.0254 (2)	0.0262 (2)	0.0169 (2)	0.01305 (19)	0.00087 (15)	0.00605 (16)
Cl1	0.0365 (4)	0.0544 (5)	0.0210 (3)	0.0184 (4)	0.0002 (3)	0.0146 (3)
Cl2	0.0274 (4)	0.0356 (4)	0.0298 (4)	0.0073 (3)	0.0041 (3)	0.0038 (3)
O1	0.0355 (12)	0.0344 (12)	0.0195 (10)	0.0152 (10)	0.0015 (8)	0.0034 (8)
O2	0.0448 (13)	0.0416 (13)	0.0261 (11)	0.0245 (11)	0.0027 (9)	0.0164 (9)
O3	0.0268 (12)	0.0332 (12)	0.0196 (11)	0.0102 (10)	0.0014 (9)	0.0074 (9)
N1	0.0218 (12)	0.0261 (13)	0.0272 (12)	0.0114 (11)	0.0029 (10)	0.0105 (10)
N2	0.0245 (13)	0.0224 (12)	0.0178 (10)	0.0128 (11)	0.0009 (9)	0.0053 (9)
N3	0.0258 (13)	0.0254 (13)	0.0254 (12)	0.0121 (11)	0.0045 (10)	0.0073 (10)
C1	0.0261 (16)	0.0313 (17)	0.0388 (18)	0.0126 (14)	0.0023 (13)	0.0176 (14)
C2	0.0284 (17)	0.0321 (18)	0.058 (2)	0.0171 (15)	0.0094 (15)	0.0208 (16)
C3	0.0355 (19)	0.0266 (17)	0.061 (2)	0.0167 (16)	0.0167 (16)	0.0100 (15)
C4	0.0270 (17)	0.0287 (16)	0.0347 (17)	0.0086 (14)	0.0097 (13)	0.0041 (13)
C5	0.0174 (14)	0.0242 (15)	0.0275 (14)	0.0068 (12)	0.0069 (11)	0.0083 (11)
C6	0.0159 (13)	0.0251 (15)	0.0209 (13)	0.0046 (12)	0.0019 (10)	0.0078 (11)
C7	0.0214 (15)	0.0231 (14)	0.0249 (14)	0.0070 (13)	0.0031 (11)	0.0101 (11)
C8	0.0220 (14)	0.0184 (14)	0.0296 (14)	0.0069 (12)	0.0056 (11)	0.0101 (11)
C9	0.0288 (17)	0.0296 (16)	0.0440 (18)	0.0141 (14)	0.0094 (14)	0.0187 (14)
C10	0.040 (2)	0.0296 (17)	0.059 (2)	0.0204 (16)	0.0166 (17)	0.0131 (16)
C11	0.045 (2)	0.0311 (18)	0.047 (2)	0.0173 (16)	0.0143 (16)	0.0010 (15)
C12	0.0374 (19)	0.0324 (17)	0.0268 (16)	0.0150 (15)	0.0063 (14)	0.0005 (13)
C13	0.036 (2)	0.068 (3)	0.0259 (17)	0.019 (2)	0.0116 (15)	0.0154 (16)

Geometric parameters (Å, º)

Fe1—N1	2.122 (2)	N3—C12	1.339 (4)
Fe1—N2	2.078 (2)	N3—C8	1.349 (3)
Fe1—N3	2.115 (2)	C1—C2	1.377 (4)
Fe1—O3	2.232 (2)	C2—C3	1.377 (5)
Fe1—Cl1	2.2554 (8)	C3—C4	1.388 (4)
Fe1—Cl2	2.2894 (9)	C4—C5	1.375 (4)
O1—C6	1.223 (3)	C5—C6	1.513 (4)
O2—C7	1.218 (3)	C7—C8	1.511 (4)
O3—C13	1.428 (4)	C8—C9	1.382 (4)
N1—C5	1.343 (3)	C9—C10	1.372 (5)
N1—C1	1.346 (3)	C10—C11	1.375 (5)
N2—C6	1.359 (3)	C11—C12	1.390 (4)
N2—C7	1.375 (3)
N2—Fe1—N1	77.24 (8)	C12—N3—Fe1	124.90 (19)
N2—Fe1—N3	77.30 (8)	C8—N3—Fe1	115.77 (17)
N3—Fe1—N1	153.99 (9)	N1—C1—C2	121.7 (3)
N1—Fe1—O3	86.84 (8)	C1—C2—C3	119.0 (3)
N2—Fe1—O3	81.22 (8)	C2—C3—C4	119.8 (3)
N3—Fe1—O3	84.13 (8)	C5—C4—C3	118.1 (3)
N1—Fe1—Cl1	100.57 (6)	N1—C5—C4	122.5 (2)
N2—Fe1—Cl1	166.55 (7)	N1—C5—C6	116.3 (2)
N3—Fe1—Cl1	102.95 (7)	C4—C5—C6	121.1 (2)
N1—Fe1—Cl2	93.91 (7)	O1—C6—N2	128.8 (2)
N2—Fe1—Cl2	95.44 (7)	O1—C6—C5	119.1 (2)
N3—Fe1—Cl2	93.69 (7)	N2—C6—C5	112.1 (2)
O3—Fe1—Cl1	85.43 (6)	O2—C7—N2	127.7 (2)
O3—Fe1—Cl2	176.34 (6)	O2—C7—C8	120.8 (2)
Cl1—Fe1—Cl2	97.95 (3)	N2—C7—C8	111.5 (2)
C13—O3—Fe1	125.2 (2)	N3—C8—C9	121.5 (3)
C5—N1—C1	118.9 (2)	N3—C8—C7	116.5 (2)
C5—N1—Fe1	115.46 (17)	C9—C8—C7	122.1 (2)
C1—N1—Fe1	125.6 (2)	C10—C9—C8	119.2 (3)
C6—N2—Fe1	118.79 (16)	C9—C10—C11	119.6 (3)
C7—N2—Fe1	118.81 (16)	C10—C11—C12	119.0 (3)
C6—N2—C7	122.3 (2)	N3—C12—C11	121.5 (3)
C12—N3—C8	119.3 (2)

(II)

Crystal data

[Fe(C12H8N3O2)Cl2(C2H6O)]	Z = 2
Mr = 399.03	F(000) = 406
Triclinic, P1	Dx = 1.675 Mg m^−3
a = 8.5609 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.5998 (6) Å	Cell parameters from 3161 reflections
c = 12.0245 (9) Å	θ = 1.8–26.0°
α = 99.744 (1)°	µ = 1.31 mm^−1
β = 99.944 (1)°	T = 193 K
γ = 110.483 (1)°	Prismatic, yellow
V = 791.13 (10) Å^3	0.32 × 0.28 × 0.15 mm

Data collection

Bruker CCD area-detector diffractometer	3059 independent reflections
Radiation source: fine-focus sealed tube	2691 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
ω scans	θmax = 26.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→9
Tmin = 0.688, Tmax = 0.862	k = −10→10
4571 measured reflections	l = −9→14

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.075	All H-atom parameters refined
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0389P)^2 + 0.2465P] where P = (Fo^2 + 2Fc^2)/3
3059 reflections	(Δ/σ)max = 0.003
264 parameters	Δρmax = 0.37 e Å^−3
0 restraints	Δρmin = −0.28 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Fe1	0.66512 (3)	0.31533 (3)	0.72254 (2)	0.02057 (10)
Cl1	0.61903 (7)	0.33115 (7)	0.53504 (4)	0.03560 (14)
Cl2	0.39447 (6)	0.12413 (6)	0.71313 (4)	0.03126 (13)
O1	0.81567 (19)	0.51071 (19)	1.08479 (11)	0.0297 (3)
O2	0.9072 (2)	0.2308 (2)	1.02608 (13)	0.0349 (4)
O3	0.93087 (18)	0.49660 (18)	0.74288 (12)	0.0236 (3)
N1	0.6237 (2)	0.5311 (2)	0.80573 (14)	0.0224 (3)
N2	0.7669 (2)	0.3437 (2)	0.89801 (13)	0.0203 (3)
N3	0.7688 (2)	0.1246 (2)	0.71827 (14)	0.0241 (3)
C1	0.5478 (3)	0.6206 (3)	0.7515 (2)	0.0292 (4)
C2	0.5196 (3)	0.7554 (3)	0.8131 (2)	0.0366 (5)
C3	0.5696 (3)	0.7984 (3)	0.9332 (2)	0.0388 (5)
C4	0.6484 (3)	0.7079 (3)	0.9902 (2)	0.0304 (5)
C5	0.6730 (2)	0.5747 (2)	0.92283 (16)	0.0219 (4)
C6	0.7603 (2)	0.4718 (2)	0.97891 (16)	0.0222 (4)
C7	0.8471 (2)	0.2374 (2)	0.92870 (17)	0.0234 (4)
C8	0.8532 (2)	0.1199 (2)	0.82211 (17)	0.0238 (4)
C9	0.9402 (3)	0.0123 (3)	0.8312 (2)	0.0325 (5)
C10	0.9365 (3)	−0.0954 (3)	0.7306 (2)	0.0428 (6)
C11	0.8453 (3)	−0.0958 (3)	0.6254 (2)	0.0433 (6)
C12	0.7623 (3)	0.0165 (3)	0.6212 (2)	0.0329 (5)
C13	1.0426 (3)	0.5283 (3)	0.66527 (19)	0.0325 (5)
C14	1.0974 (4)	0.3882 (3)	0.6272 (2)	0.0442 (6)
H1	0.518 (3)	0.590 (3)	0.678 (2)	0.030 (6)*
H2	0.460 (4)	0.814 (4)	0.770 (2)	0.054 (8)*
H3A	0.550 (3)	0.889 (3)	0.979 (2)	0.040 (7)*
H3B	0.985 (3)	0.519 (3)	0.798 (2)	0.030 (7)*
H4	0.685 (3)	0.733 (3)	1.075 (2)	0.031 (6)*
H9	0.993 (4)	0.010 (3)	0.902 (2)	0.051 (8)*
H10	0.996 (3)	−0.172 (3)	0.731 (2)	0.047 (7)*
H11	0.841 (3)	−0.166 (3)	0.552 (2)	0.046 (7)*
H12	0.704 (3)	0.025 (3)	0.554 (2)	0.027 (6)*
H13A	0.979 (3)	0.552 (3)	0.599 (2)	0.037 (6)*
H13B	1.135 (3)	0.639 (3)	0.701 (2)	0.039 (7)*
H14A	1.161 (4)	0.361 (3)	0.703 (3)	0.050 (8)*
H14B	1.191 (4)	0.424 (4)	0.574 (3)	0.072 (10)*
H14C	0.986 (5)	0.268 (5)	0.564 (3)	0.088 (11)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe1	0.02427 (16)	0.02205 (16)	0.01501 (15)	0.01079 (12)	0.00068 (10)	0.00417 (10)
Cl1	0.0370 (3)	0.0436 (3)	0.0188 (2)	0.0099 (2)	−0.0020 (2)	0.0109 (2)
Cl2	0.0260 (3)	0.0311 (3)	0.0314 (3)	0.0077 (2)	0.0048 (2)	0.0042 (2)
O1	0.0347 (8)	0.0350 (8)	0.0162 (7)	0.0142 (7)	0.0015 (6)	0.0016 (6)
O2	0.0450 (9)	0.0415 (9)	0.0251 (8)	0.0238 (8)	0.0036 (7)	0.0160 (7)
O3	0.0238 (7)	0.0287 (7)	0.0158 (7)	0.0101 (6)	0.0008 (6)	0.0041 (6)
N1	0.0198 (8)	0.0220 (8)	0.0258 (8)	0.0091 (6)	0.0023 (6)	0.0081 (6)
N2	0.0237 (8)	0.0220 (8)	0.0164 (7)	0.0115 (7)	0.0022 (6)	0.0051 (6)
N3	0.0267 (8)	0.0194 (8)	0.0244 (8)	0.0092 (7)	0.0044 (7)	0.0024 (6)
C1	0.0243 (10)	0.0284 (10)	0.0358 (12)	0.0111 (8)	0.0026 (9)	0.0138 (9)
C2	0.0262 (11)	0.0273 (11)	0.0612 (16)	0.0132 (9)	0.0093 (10)	0.0191 (11)
C3	0.0333 (12)	0.0246 (11)	0.0632 (16)	0.0146 (9)	0.0200 (11)	0.0075 (10)
C4	0.0276 (11)	0.0247 (10)	0.0374 (13)	0.0090 (8)	0.0115 (9)	0.0028 (9)
C5	0.0197 (9)	0.0208 (9)	0.0236 (10)	0.0064 (7)	0.0052 (7)	0.0042 (7)
C6	0.0209 (9)	0.0231 (9)	0.0212 (10)	0.0071 (8)	0.0045 (7)	0.0060 (7)
C7	0.0213 (9)	0.0238 (9)	0.0246 (10)	0.0077 (8)	0.0035 (8)	0.0095 (8)
C8	0.0222 (9)	0.0184 (9)	0.0290 (10)	0.0063 (8)	0.0042 (8)	0.0072 (8)
C9	0.0303 (11)	0.0270 (11)	0.0445 (13)	0.0150 (9)	0.0078 (10)	0.0133 (9)
C10	0.0387 (13)	0.0286 (12)	0.0659 (17)	0.0201 (11)	0.0146 (12)	0.0070 (11)
C11	0.0482 (14)	0.0292 (12)	0.0506 (15)	0.0180 (11)	0.0163 (12)	−0.0052 (11)
C12	0.0361 (12)	0.0279 (11)	0.0290 (12)	0.0104 (9)	0.0061 (9)	−0.0012 (9)
C13	0.0292 (11)	0.0432 (13)	0.0241 (10)	0.0120 (10)	0.0070 (9)	0.0104 (9)
C14	0.0499 (15)	0.0454 (14)	0.0414 (14)	0.0193 (12)	0.0195 (12)	0.0113 (11)

Geometric parameters (Å, º)

Fe1—N1	2.1269 (16)	N3—C8	1.345 (3)
Fe1—N2	2.0767 (15)	N3—C12	1.343 (3)
Fe1—N3	2.1187 (16)	C1—C2	1.386 (3)
Fe1—O3	2.2051 (15)	C2—C3	1.378 (4)
Fe1—Cl1	2.2564 (6)	C3—C4	1.385 (3)
Fe1—Cl2	2.2946 (6)	C4—C5	1.388 (3)
O1—C6	1.222 (2)	C5—C6	1.512 (3)
O2—C7	1.214 (2)	C7—C8	1.513 (3)
O3—C13	1.440 (3)	C8—C9	1.382 (3)
N1—C1	1.347 (2)	C9—C10	1.382 (3)
N1—C5	1.344 (2)	C10—C11	1.366 (4)
N2—C6	1.365 (2)	C11—C12	1.388 (3)
N2—C7	1.381 (2)	C13—C14	1.471 (3)
N2—Fe1—N1	77.00 (6)	C12—N3—Fe1	125.16 (15)
N2—Fe1—N3	77.37 (6)	C8—N3—Fe1	115.62 (12)
N3—Fe1—N1	154.07 (6)	N1—C1—C2	121.7 (2)
N1—Fe1—O3	86.00 (6)	C3—C2—C1	119.1 (2)
N2—Fe1—O3	80.23 (6)	C2—C3—C4	119.8 (2)
N3—Fe1—O3	85.88 (6)	C3—C4—C5	118.0 (2)
N1—Fe1—Cl1	101.72 (5)	N1—C5—C4	122.66 (18)
N2—Fe1—Cl1	166.05 (5)	N1—C5—C6	116.37 (16)
N3—Fe1—Cl1	102.18 (5)	C4—C5—C6	120.96 (18)
O3—Fe1—Cl1	85.83 (4)	O1—C6—N2	128.79 (18)
N1—Fe1—Cl2	93.93 (5)	O1—C6—C5	119.43 (17)
N2—Fe1—Cl2	96.11 (5)	N2—C6—C5	111.77 (16)
N3—Fe1—Cl2	92.62 (5)	O2—C7—N2	127.85 (18)
Cl1—Fe1—Cl2	97.84 (2)	O2—C7—C8	120.83 (17)
O3—Fe1—Cl2	176.26 (4)	N2—C7—C8	111.33 (16)
C13—O3—Fe1	133.77 (13)	N3—C8—C9	121.75 (19)
C5—N1—C1	118.71 (18)	N3—C8—C7	116.62 (16)
C5—N1—Fe1	115.58 (12)	C9—C8—C7	121.63 (19)
C1—N1—Fe1	125.66 (15)	C10—C9—C8	118.7 (2)
C6—N2—Fe1	119.18 (12)	C11—C10—C9	119.7 (2)
C7—N2—Fe1	118.74 (12)	C10—C11—C12	119.1 (2)
C6—N2—C7	122.00 (15)	N3—C12—C11	121.5 (2)
C12—N3—C8	119.15 (18)	O3—C13—C14	114.76 (19)