Chloro(2,3,7,8,12,13,17,18-octaethyl­porphyrinato)­iron(III)

The molecular structure of the title compound, [Fe(C₃₆H₄₄N₄)Cl], was determined by single-crystal X-ray diffraction at 130 K. The compound is characterized by an average Fe-N bond length of 2.071 (2) Å and an Fe-Cl bond length of 2.231 (1) Å.

Key indicators

• Single-crystal X-ray study
• T = 126 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.048
• wR factor = 0.137
• Data-to-parameter ratio = 18.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.99 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.45 Ratio

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: P3 (Siemens, 1995); cell refinement: P3; data reduction: XDISK (Siemens, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1995); software used to prepare material for publication: SHELXL97.

Chloro(2,3,7,8,12,13,17,18-octaethylporphyrinato)iron(III)

Crystal data

[Fe(C36H44N4)Cl]	F(000) = 1324
Mr = 624.05	Dx = 1.298 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 15.045 (9) Å	Cell parameters from 42 reflections
b = 22.154 (12) Å	θ = 18–22°
c = 9.972 (5) Å	µ = 0.59 mm^−1
β = 106.05 (4)°	T = 126 K
V = 3194 (3) Å^3	Parallelepiped, blue
Z = 4	0.53 × 0.30 × 0.25 mm

Data collection

Siemens R3m/V diffractometer	5419 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.032
Graphite monochromator	θmax = 27.5°, θmin = 1.4°
ω scans	h = −19→18
Absorption correction: part of the refinement model (ΔF) (XABS2; Parkin et al., 1995)	k = 0→28
Tmin = 0.787, Tmax = 0.867	l = 0→12
7953 measured reflections	2 standard reflections every 198 reflections
7331 independent reflections	intensity decay: none

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.137	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0678P)^2 + 1.2711P] where P = (Fo^2 + 2Fc^2)/3
7331 reflections	(Δ/σ)max = 0.001
387 parameters	Δρmax = 0.41 e Å^−3
0 restraints	Δρmin = −0.77 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. Hydrogen atoms were placed in geometrical positions and refined using a riding model. Higher thermal motion was observed for some of the methyl groups.

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

	x	y	z	Uiso*/Ueq
Fe	0.75737 (2)	0.044079 (16)	0.24840 (4)	0.01908 (11)
Cl1	0.78494 (5)	0.10084 (3)	0.44035 (7)	0.02525 (15)
N21	0.79461 (14)	−0.04256 (9)	0.3213 (2)	0.0180 (4)
N22	0.62083 (14)	0.01625 (10)	0.2117 (2)	0.0197 (4)
N23	0.70982 (14)	0.10724 (9)	0.0926 (2)	0.0174 (4)
N24	0.88426 (14)	0.04923 (9)	0.2064 (2)	0.0168 (4)
C1	0.88364 (17)	−0.06467 (11)	0.3672 (3)	0.0185 (5)
C2	0.88514 (17)	−0.12138 (11)	0.4391 (3)	0.0196 (5)
C21	0.97013 (19)	−0.15909 (12)	0.4970 (3)	0.0269 (6)
H21A	0.9574	−0.1891	0.5629	0.032*
H21B	1.0210	−0.1328	0.5497	0.032*
C22	1.0009 (2)	−0.19209 (14)	0.3827 (4)	0.0355 (7)
H22A	0.9487	−0.2150	0.3243	0.053*
H22B	1.0515	−0.2198	0.4256	0.053*
H22C	1.0221	−0.1626	0.3251	0.053*
C3	0.79580 (17)	−0.13355 (11)	0.4366 (3)	0.0205 (5)
C31	0.75974 (19)	−0.18780 (12)	0.4942 (3)	0.0282 (6)
H31A	0.7084	−0.1752	0.5322	0.034*
H31B	0.8096	−0.2044	0.5723	0.034*
C32	0.7253 (2)	−0.23725 (14)	0.3871 (4)	0.0456 (9)
H32A	0.6747	−0.2216	0.3106	0.068*
H32B	0.7030	−0.2714	0.4313	0.068*
H32C	0.7760	−0.2507	0.3503	0.068*
C4	0.74011 (17)	−0.08438 (11)	0.3639 (3)	0.0187 (5)
C5	0.64446 (17)	−0.07927 (11)	0.3396 (3)	0.0206 (5)
H5	0.6144	−0.1108	0.3749	0.025*
C6	0.58879 (17)	−0.03287 (11)	0.2691 (3)	0.0200 (5)
C7	0.48928 (17)	−0.02939 (12)	0.2442 (3)	0.0204 (5)
C71	0.43052 (18)	−0.07455 (12)	0.2917 (3)	0.0229 (5)
H71A	0.4590	−0.1150	0.2938	0.028*
H71B	0.3689	−0.0759	0.2227	0.028*
C72	0.4179 (2)	−0.06114 (14)	0.4348 (3)	0.0331 (7)
H72A	0.4780	−0.0630	0.5051	0.050*
H72B	0.3761	−0.0911	0.4570	0.050*
H72C	0.3914	−0.0207	0.4346	0.050*
C8	0.46162 (17)	0.02246 (12)	0.1707 (3)	0.0218 (5)
C81	0.36580 (18)	0.04863 (13)	0.1224 (3)	0.0287 (6)
H81A	0.3199	0.0163	0.1196	0.034*
H81B	0.3553	0.0646	0.0266	0.034*
C82	0.3514 (2)	0.09908 (14)	0.2180 (4)	0.0367 (7)
H82A	0.3579	0.0828	0.3117	0.055*
H82B	0.2893	0.1161	0.1811	0.055*
H82C	0.3977	0.1307	0.2229	0.055*
C9	0.54368 (17)	0.05025 (12)	0.1505 (3)	0.0199 (5)
C10	0.54424 (17)	0.10292 (12)	0.0755 (3)	0.0215 (5)
H10	0.4867	0.1230	0.0405	0.026*
C11	0.62062 (17)	0.12913 (11)	0.0465 (3)	0.0197 (5)
C12	0.61788 (18)	0.18179 (11)	−0.0402 (3)	0.0206 (5)
C121	0.53164 (19)	0.21684 (13)	−0.1103 (3)	0.0254 (6)
H12A	0.4798	0.1882	−0.1443	0.030*
H12B	0.5413	0.2381	−0.1925	0.030*
C122	0.5051 (3)	0.26268 (17)	−0.0151 (4)	0.0502 (10)
H12C	0.4908	0.2417	0.0630	0.075*
H12D	0.4507	0.2853	−0.0677	0.075*
H12E	0.5567	0.2906	0.0210	0.075*
C13	0.70646 (17)	0.19151 (11)	−0.0467 (3)	0.0190 (5)
C131	0.74112 (19)	0.23819 (12)	−0.1284 (3)	0.0263 (6)
H13A	0.7949	0.2591	−0.0656	0.032*
H13B	0.6920	0.2686	−0.1636	0.032*
C132	0.7698 (2)	0.21168 (15)	−0.2514 (3)	0.0390 (8)
H13C	0.8181	0.1813	−0.2174	0.058*
H13D	0.7936	0.2439	−0.2992	0.058*
H13E	0.7160	0.1928	−0.3167	0.058*
C14	0.76315 (17)	0.14534 (11)	0.0386 (3)	0.0189 (5)
C15	0.85867 (17)	0.14137 (11)	0.0654 (3)	0.0192 (5)
H15	0.8881	0.1719	0.0262	0.023*
C16	0.91568 (17)	0.09703 (11)	0.1443 (3)	0.0181 (5)
C17	1.01524 (17)	0.09338 (11)	0.1687 (3)	0.0201 (5)
C171	1.07408 (18)	0.13723 (12)	0.1167 (3)	0.0255 (6)
H17A	1.1329	0.1433	0.1902	0.031*
H17B	1.0419	0.1766	0.0993	0.031*
C172	1.0956 (3)	0.11656 (19)	−0.0165 (3)	0.0510 (10)
H17C	1.1301	0.0785	0.0010	0.076*
H17D	1.1329	0.1474	−0.0464	0.076*
H17E	1.0377	0.1105	−0.0899	0.076*
C18	1.04390 (16)	0.04315 (11)	0.2469 (3)	0.0172 (5)
C181	1.13968 (17)	0.01782 (12)	0.2968 (3)	0.0216 (5)
H18A	1.1509	0.0045	0.3948	0.026*
H18B	1.1849	0.0500	0.2946	0.026*
C182	1.15547 (19)	−0.03535 (13)	0.2086 (3)	0.0288 (6)
H18C	1.1117	−0.0677	0.2117	0.043*
H18D	1.2189	−0.0503	0.2457	0.043*
H18E	1.1460	−0.0222	0.1119	0.043*
C19	0.96202 (16)	0.01597 (11)	0.2711 (2)	0.0170 (5)
C20	0.96147 (17)	−0.03623 (11)	0.3465 (3)	0.0181 (5)
H20	1.0197	−0.0545	0.3884	0.022*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe	0.01857 (19)	0.01953 (19)	0.0193 (2)	0.00117 (14)	0.00550 (14)	0.00112 (15)
Cl1	0.0293 (3)	0.0241 (3)	0.0224 (3)	0.0001 (3)	0.0072 (3)	−0.0025 (3)
N21	0.0176 (10)	0.0169 (10)	0.0196 (11)	0.0012 (8)	0.0053 (8)	0.0017 (8)
N22	0.0176 (10)	0.0221 (11)	0.0187 (11)	0.0021 (8)	0.0040 (8)	0.0010 (9)
N23	0.0159 (10)	0.0179 (10)	0.0175 (10)	0.0009 (8)	0.0032 (8)	0.0030 (8)
N24	0.0171 (10)	0.0174 (10)	0.0159 (10)	0.0020 (8)	0.0044 (8)	0.0026 (8)
C1	0.0209 (12)	0.0177 (11)	0.0174 (12)	0.0025 (9)	0.0061 (10)	0.0016 (10)
C2	0.0223 (12)	0.0171 (12)	0.0191 (12)	0.0011 (10)	0.0054 (10)	0.0016 (10)
C21	0.0241 (13)	0.0244 (14)	0.0318 (15)	0.0020 (11)	0.0069 (12)	0.0086 (12)
C22	0.0303 (15)	0.0268 (15)	0.050 (2)	0.0085 (12)	0.0118 (14)	0.0013 (14)
C3	0.0230 (13)	0.0184 (12)	0.0202 (13)	0.0013 (10)	0.0061 (10)	0.0006 (10)
C31	0.0239 (13)	0.0220 (13)	0.0384 (16)	0.0000 (11)	0.0078 (12)	0.0082 (12)
C32	0.0402 (18)	0.0232 (15)	0.068 (2)	−0.0069 (13)	0.0055 (17)	−0.0036 (16)
C4	0.0213 (12)	0.0170 (11)	0.0185 (12)	−0.0009 (9)	0.0064 (10)	0.0003 (10)
C5	0.0199 (12)	0.0177 (12)	0.0251 (13)	−0.0014 (9)	0.0081 (10)	−0.0008 (10)
C6	0.0197 (12)	0.0229 (13)	0.0186 (13)	−0.0029 (10)	0.0076 (10)	−0.0049 (10)
C7	0.0166 (12)	0.0250 (13)	0.0198 (12)	−0.0016 (10)	0.0056 (10)	−0.0060 (10)
C71	0.0181 (12)	0.0226 (13)	0.0288 (14)	−0.0041 (10)	0.0076 (11)	−0.0055 (11)
C72	0.0360 (16)	0.0349 (16)	0.0311 (16)	−0.0108 (13)	0.0136 (13)	−0.0054 (13)
C8	0.0165 (12)	0.0267 (13)	0.0218 (13)	−0.0014 (10)	0.0048 (10)	−0.0043 (11)
C81	0.0169 (12)	0.0340 (15)	0.0345 (16)	0.0003 (11)	0.0057 (11)	0.0060 (13)
C82	0.0253 (15)	0.0361 (17)	0.053 (2)	0.0082 (12)	0.0171 (14)	0.0039 (15)
C9	0.0164 (11)	0.0243 (13)	0.0184 (12)	0.0008 (10)	0.0038 (10)	−0.0034 (10)
C10	0.0171 (12)	0.0285 (13)	0.0177 (12)	0.0051 (10)	0.0029 (10)	0.0021 (11)
C11	0.0212 (12)	0.0225 (13)	0.0147 (12)	0.0024 (10)	0.0039 (10)	−0.0012 (10)
C12	0.0243 (13)	0.0217 (12)	0.0140 (12)	0.0040 (10)	0.0021 (10)	−0.0017 (10)
C121	0.0242 (13)	0.0290 (14)	0.0217 (13)	0.0080 (11)	0.0041 (11)	0.0069 (11)
C122	0.049 (2)	0.048 (2)	0.047 (2)	0.0279 (17)	0.0029 (16)	−0.0108 (17)
C13	0.0238 (12)	0.0172 (12)	0.0142 (12)	0.0028 (9)	0.0024 (10)	−0.0006 (10)
C131	0.0267 (14)	0.0205 (13)	0.0299 (15)	0.0015 (10)	0.0048 (12)	0.0060 (11)
C132	0.0475 (19)	0.0403 (18)	0.0340 (17)	0.0092 (15)	0.0192 (15)	0.0152 (14)
C14	0.0218 (12)	0.0182 (12)	0.0162 (12)	0.0018 (9)	0.0044 (10)	−0.0016 (10)
C15	0.0212 (12)	0.0158 (11)	0.0202 (13)	−0.0018 (9)	0.0051 (10)	0.0019 (10)
C16	0.0184 (12)	0.0168 (11)	0.0189 (12)	0.0012 (9)	0.0049 (10)	−0.0015 (10)
C17	0.0188 (12)	0.0191 (12)	0.0225 (13)	−0.0026 (9)	0.0060 (10)	−0.0019 (10)
C171	0.0193 (12)	0.0213 (13)	0.0350 (16)	−0.0007 (10)	0.0057 (11)	0.0063 (11)
C172	0.050 (2)	0.076 (3)	0.0285 (17)	−0.0317 (19)	0.0139 (15)	0.0024 (17)
C18	0.0165 (11)	0.0182 (11)	0.0168 (12)	−0.0007 (9)	0.0043 (9)	−0.0017 (10)
C181	0.0163 (12)	0.0211 (12)	0.0271 (14)	−0.0002 (10)	0.0053 (10)	0.0002 (11)
C182	0.0229 (13)	0.0298 (15)	0.0348 (16)	0.0032 (11)	0.0097 (12)	−0.0054 (12)
C19	0.0164 (11)	0.0190 (12)	0.0154 (12)	0.0009 (9)	0.0040 (9)	−0.0028 (10)
C20	0.0161 (11)	0.0192 (12)	0.0189 (12)	0.0024 (9)	0.0049 (9)	−0.0008 (10)

Geometric parameters (Å, º)

Fe—N23	2.066 (2)	C81—H81B	0.9900
Fe—N24	2.067 (2)	C82—H82A	0.9800
Fe—N21	2.074 (2)	C82—H82B	0.9800
Fe—N22	2.078 (2)	C82—H82C	0.9800
Fe—Cl1	2.2312 (12)	C9—C10	1.387 (4)
N21—C4	1.380 (3)	C10—C11	1.387 (4)
N21—C1	1.380 (3)	C10—H10	0.9500
N22—C9	1.377 (3)	C11—C12	1.446 (4)
N22—C6	1.377 (3)	C12—C13	1.369 (4)
N23—C14	1.373 (3)	C12—C121	1.508 (4)
N23—C11	1.381 (3)	C121—C122	1.518 (4)
N24—C16	1.375 (3)	C121—H12A	0.9900
N24—C19	1.382 (3)	C121—H12B	0.9900
C1—C20	1.394 (3)	C122—H12C	0.9800
C1—C2	1.444 (3)	C122—H12D	0.9800
C2—C3	1.364 (4)	C122—H12E	0.9800
C2—C21	1.503 (4)	C13—C14	1.448 (3)
C21—C22	1.529 (4)	C13—C131	1.497 (4)
C21—H21A	0.9900	C131—C132	1.526 (4)
C21—H21B	0.9900	C131—H13A	0.9900
C22—H22A	0.9800	C131—H13B	0.9900
C22—H22B	0.9800	C132—H13C	0.9800
C22—H22C	0.9800	C132—H13D	0.9800
C3—C4	1.442 (3)	C132—H13E	0.9800
C3—C31	1.497 (4)	C14—C15	1.390 (3)
C31—C32	1.517 (4)	C15—C16	1.395 (3)
C31—H31A	0.9900	C15—H15	0.9500
C31—H31B	0.9900	C16—C17	1.452 (3)
C32—H32A	0.9800	C17—C18	1.359 (4)
C32—H32B	0.9800	C17—C171	1.500 (3)
C32—H32C	0.9800	C171—C172	1.522 (4)
C4—C5	1.396 (3)	C171—H17A	0.9900
C5—C6	1.388 (4)	C171—H17B	0.9900
C5—H5	0.9500	C172—H17C	0.9800
C6—C7	1.450 (3)	C172—H17D	0.9800
C7—C8	1.364 (4)	C172—H17E	0.9800
C7—C71	1.496 (4)	C18—C19	1.450 (3)
C71—C72	1.521 (4)	C18—C181	1.497 (3)
C71—H71A	0.9900	C181—C182	1.527 (4)
C71—H71B	0.9900	C181—H18A	0.9900
C72—H72A	0.9800	C181—H18B	0.9900
C72—H72B	0.9800	C182—H18C	0.9800
C72—H72C	0.9800	C182—H18D	0.9800
C8—C9	1.443 (3)	C182—H18E	0.9800
C8—C81	1.504 (4)	C19—C20	1.381 (3)
C81—C82	1.523 (4)	C20—H20	0.9500
C81—H81A	0.9900
N23—Fe—N24	87.57 (9)	C81—C82—H82B	109.5
N23—Fe—N21	153.41 (8)	H82A—C82—H82B	109.5
N24—Fe—N21	86.95 (8)	C81—C82—H82C	109.5
N23—Fe—N22	87.06 (9)	H82A—C82—H82C	109.5
N24—Fe—N22	154.68 (9)	H82B—C82—H82C	109.5
N21—Fe—N22	86.86 (9)	N22—C9—C10	124.7 (2)
N23—Fe—Cl1	101.94 (8)	N22—C9—C8	110.7 (2)
N24—Fe—Cl1	100.34 (7)	C10—C9—C8	124.6 (2)
N21—Fe—Cl1	104.64 (7)	C11—C10—C9	126.4 (2)
N22—Fe—Cl1	104.98 (7)	C11—C10—H10	116.8
C4—N21—C1	105.3 (2)	C9—C10—H10	116.8
C4—N21—Fe	127.11 (17)	N23—C11—C10	124.7 (2)
C1—N21—Fe	126.02 (16)	N23—C11—C12	110.3 (2)
C9—N22—C6	105.5 (2)	C10—C11—C12	125.0 (2)
C9—N22—Fe	125.93 (18)	C13—C12—C11	106.7 (2)
C6—N22—Fe	127.14 (17)	C13—C12—C121	128.4 (2)
C14—N23—C11	105.8 (2)	C11—C12—C121	124.9 (2)
C14—N23—Fe	126.37 (17)	C12—C121—C122	113.3 (2)
C11—N23—Fe	126.22 (16)	C12—C121—H12A	108.9
C16—N24—C19	105.6 (2)	C122—C121—H12A	108.9
C16—N24—Fe	125.83 (16)	C12—C121—H12B	108.9
C19—N24—Fe	125.88 (16)	C122—C121—H12B	108.9
N21—C1—C20	124.7 (2)	H12A—C121—H12B	107.7
N21—C1—C2	110.7 (2)	C121—C122—H12C	109.5
C20—C1—C2	124.6 (2)	C121—C122—H12D	109.5
C3—C2—C1	106.4 (2)	H12C—C122—H12D	109.5
C3—C2—C21	128.8 (2)	C121—C122—H12E	109.5
C1—C2—C21	124.7 (2)	H12C—C122—H12E	109.5
C2—C21—C22	112.4 (2)	H12D—C122—H12E	109.5
C2—C21—H21A	109.1	C12—C13—C14	106.5 (2)
C22—C21—H21A	109.1	C12—C13—C131	128.7 (2)
C2—C21—H21B	109.1	C14—C13—C131	124.8 (2)
C22—C21—H21B	109.1	C13—C131—C132	113.0 (2)
H21A—C21—H21B	107.9	C13—C131—H13A	109.0
C21—C22—H22A	109.5	C132—C131—H13A	109.0
C21—C22—H22B	109.5	C13—C131—H13B	109.0
H22A—C22—H22B	109.5	C132—C131—H13B	109.0
C21—C22—H22C	109.5	H13A—C131—H13B	107.8
H22A—C22—H22C	109.5	C131—C132—H13C	109.5
H22B—C22—H22C	109.5	C131—C132—H13D	109.5
C2—C3—C4	107.0 (2)	H13C—C132—H13D	109.5
C2—C3—C31	127.7 (2)	C131—C132—H13E	109.5
C4—C3—C31	125.3 (2)	H13C—C132—H13E	109.5
C3—C31—C32	113.5 (3)	H13D—C132—H13E	109.5
C3—C31—H31A	108.9	N23—C14—C15	124.8 (2)
C32—C31—H31A	108.9	N23—C14—C13	110.6 (2)
C3—C31—H31B	108.9	C15—C14—C13	124.6 (2)
C32—C31—H31B	108.9	C14—C15—C16	126.5 (2)
H31A—C31—H31B	107.7	C14—C15—H15	116.7
C31—C32—H32A	109.5	C16—C15—H15	116.7
C31—C32—H32B	109.5	N24—C16—C15	124.2 (2)
H32A—C32—H32B	109.5	N24—C16—C17	110.4 (2)
C31—C32—H32C	109.5	C15—C16—C17	125.4 (2)
H32A—C32—H32C	109.5	C18—C17—C16	106.9 (2)
H32B—C32—H32C	109.5	C18—C17—C171	127.2 (2)
N21—C4—C5	124.3 (2)	C16—C17—C171	125.9 (2)
N21—C4—C3	110.5 (2)	C17—C171—C172	113.3 (2)
C5—C4—C3	125.2 (2)	C17—C171—H17A	108.9
C6—C5—C4	126.6 (2)	C172—C171—H17A	108.9
C6—C5—H5	116.7	C17—C171—H17B	108.9
C4—C5—H5	116.7	C172—C171—H17B	108.9
N22—C6—C5	124.3 (2)	H17A—C171—H17B	107.7
N22—C6—C7	110.5 (2)	C171—C172—H17C	109.5
C5—C6—C7	125.2 (2)	C171—C172—H17D	109.5
C8—C7—C6	106.5 (2)	H17C—C172—H17D	109.5
C8—C7—C71	127.9 (2)	C171—C172—H17E	109.5
C6—C7—C71	125.6 (2)	H17C—C172—H17E	109.5
C7—C71—C72	113.9 (2)	H17D—C172—H17E	109.5
C7—C71—H71A	108.8	C17—C18—C19	106.6 (2)
C72—C71—H71A	108.8	C17—C18—C181	128.4 (2)
C7—C71—H71B	108.8	C19—C18—C181	125.0 (2)
C72—C71—H71B	108.8	C18—C181—C182	112.7 (2)
H71A—C71—H71B	107.7	C18—C181—H18A	109.0
C71—C72—H72A	109.5	C182—C181—H18A	109.0
C71—C72—H72B	109.5	C18—C181—H18B	109.0
H72A—C72—H72B	109.5	C182—C181—H18B	109.0
C71—C72—H72C	109.5	H18A—C181—H18B	107.8
H72A—C72—H72C	109.5	C181—C182—H18C	109.5
H72B—C72—H72C	109.5	C181—C182—H18D	109.5
C7—C8—C9	106.8 (2)	H18C—C182—H18D	109.5
C7—C8—C81	128.3 (2)	C181—C182—H18E	109.5
C9—C8—C81	124.9 (2)	H18C—C182—H18E	109.5
C8—C81—C82	111.9 (2)	H18D—C182—H18E	109.5
C8—C81—H81A	109.2	C20—C19—N24	124.7 (2)
C82—C81—H81A	109.2	C20—C19—C18	124.9 (2)
C8—C81—H81B	109.2	N24—C19—C18	110.5 (2)
C82—C81—H81B	109.2	C19—C20—C1	126.2 (2)
H81A—C81—H81B	107.9	C19—C20—H20	116.9
C81—C82—H82A	109.5	C1—C20—H20	116.9
N23—Fe—N21—C4	−95.6 (3)	C6—C7—C8—C81	−177.7 (3)
N24—Fe—N21—C4	−174.0 (2)	C71—C7—C8—C81	2.1 (5)
N22—Fe—N21—C4	−18.6 (2)	C7—C8—C81—C82	100.0 (3)
Cl1—Fe—N21—C4	86.1 (2)	C9—C8—C81—C82	−77.6 (3)
N23—Fe—N21—C1	100.6 (3)	C6—N22—C9—C10	−177.4 (2)
N24—Fe—N21—C1	22.2 (2)	Fe—N22—C9—C10	15.4 (4)
N22—Fe—N21—C1	177.6 (2)	C6—N22—C9—C8	0.6 (3)
Cl1—Fe—N21—C1	−77.7 (2)	Fe—N22—C9—C8	−166.66 (17)
N23—Fe—N22—C9	−22.3 (2)	C7—C8—C9—N22	−0.5 (3)
N24—Fe—N22—C9	−100.3 (3)	C81—C8—C9—N22	177.5 (2)
N21—Fe—N22—C9	−176.4 (2)	C7—C8—C9—C10	177.4 (2)
Cl1—Fe—N22—C9	79.3 (2)	C81—C8—C9—C10	−4.5 (4)
N23—Fe—N22—C6	173.2 (2)	N22—C9—C10—C11	1.8 (4)
N24—Fe—N22—C6	95.2 (3)	C8—C9—C10—C11	−175.9 (2)
N21—Fe—N22—C6	19.1 (2)	C14—N23—C11—C10	178.7 (2)
Cl1—Fe—N22—C6	−85.2 (2)	Fe—N23—C11—C10	−14.9 (4)
N24—Fe—N23—C14	−19.0 (2)	C14—N23—C11—C12	0.8 (3)
N21—Fe—N23—C14	−97.3 (3)	Fe—N23—C11—C12	167.19 (16)
N22—Fe—N23—C14	−174.3 (2)	C9—C10—C11—N23	−2.1 (4)
Cl1—Fe—N23—C14	81.0 (2)	C9—C10—C11—C12	175.5 (3)
N24—Fe—N23—C11	177.3 (2)	N23—C11—C12—C13	0.2 (3)
N21—Fe—N23—C11	99.1 (2)	C10—C11—C12—C13	−177.6 (2)
N22—Fe—N23—C11	22.1 (2)	N23—C11—C12—C121	179.0 (2)
Cl1—Fe—N23—C11	−82.6 (2)	C10—C11—C12—C121	1.1 (4)
N23—Fe—N24—C16	23.1 (2)	C13—C12—C121—C122	−98.5 (3)
N21—Fe—N24—C16	177.1 (2)	C11—C12—C121—C122	83.0 (4)
N22—Fe—N24—C16	101.0 (3)	C11—C12—C13—C14	−1.2 (3)
Cl1—Fe—N24—C16	−78.6 (2)	C121—C12—C13—C14	−179.8 (2)
N23—Fe—N24—C19	−178.2 (2)	C11—C12—C13—C131	176.6 (2)
N21—Fe—N24—C19	−24.3 (2)	C121—C12—C13—C131	−2.1 (4)
N22—Fe—N24—C19	−100.4 (3)	C12—C13—C131—C132	−108.6 (3)
Cl1—Fe—N24—C19	80.1 (2)	C14—C13—C131—C132	68.8 (3)
C4—N21—C1—C20	−179.9 (2)	C11—N23—C14—C15	176.6 (2)
Fe—N21—C1—C20	−13.2 (4)	Fe—N23—C14—C15	10.2 (4)
C4—N21—C1—C2	0.3 (3)	C11—N23—C14—C13	−1.6 (3)
Fe—N21—C1—C2	166.94 (16)	Fe—N23—C14—C13	−167.91 (16)
N21—C1—C2—C3	0.0 (3)	C12—C13—C14—N23	1.7 (3)
C20—C1—C2—C3	−179.9 (2)	C131—C13—C14—N23	−176.1 (2)
N21—C1—C2—C21	177.2 (2)	C12—C13—C14—C15	−176.4 (2)
C20—C1—C2—C21	−2.6 (4)	C131—C13—C14—C15	5.7 (4)
C3—C2—C21—C22	102.3 (3)	N23—C14—C15—C16	3.6 (4)
C1—C2—C21—C22	−74.4 (3)	C13—C14—C15—C16	−178.5 (2)
C1—C2—C3—C4	−0.2 (3)	C19—N24—C16—C15	178.9 (2)
C21—C2—C3—C4	−177.3 (3)	Fe—N24—C16—C15	−18.9 (3)
C1—C2—C3—C31	178.4 (3)	C19—N24—C16—C17	0.8 (3)
C21—C2—C3—C31	1.3 (5)	Fe—N24—C16—C17	162.93 (17)
C2—C3—C31—C32	−94.3 (3)	C14—C15—C16—N24	1.0 (4)
C4—C3—C31—C32	84.1 (3)	C14—C15—C16—C17	178.9 (2)
C1—N21—C4—C5	179.5 (2)	N24—C16—C17—C18	−0.3 (3)
Fe—N21—C4—C5	13.0 (4)	C15—C16—C17—C18	−178.5 (2)
C1—N21—C4—C3	−0.4 (3)	N24—C16—C17—C171	179.7 (2)
Fe—N21—C4—C3	−166.87 (17)	C15—C16—C17—C171	1.6 (4)
C2—C3—C4—N21	0.4 (3)	C18—C17—C171—C172	82.5 (4)
C31—C3—C4—N21	−178.3 (2)	C16—C17—C171—C172	−97.5 (3)
C2—C3—C4—C5	−179.5 (2)	C16—C17—C18—C19	−0.2 (3)
C31—C3—C4—C5	1.8 (4)	C171—C17—C18—C19	179.7 (2)
N21—C4—C5—C6	0.7 (4)	C16—C17—C18—C181	177.9 (2)
C3—C4—C5—C6	−179.4 (3)	C171—C17—C18—C181	−2.1 (4)
C9—N22—C6—C5	179.0 (2)	C17—C18—C181—C182	−100.9 (3)
Fe—N22—C6—C5	−14.0 (4)	C19—C18—C181—C182	76.9 (3)
C9—N22—C6—C7	−0.4 (3)	C16—N24—C19—C20	179.9 (2)
Fe—N22—C6—C7	166.63 (17)	Fe—N24—C19—C20	17.7 (3)
C4—C5—C6—N22	−0.2 (4)	C16—N24—C19—C18	−0.9 (3)
C4—C5—C6—C7	179.1 (2)	Fe—N24—C19—C18	−163.06 (16)
N22—C6—C7—C8	0.1 (3)	C17—C18—C19—C20	179.9 (2)
C5—C6—C7—C8	−179.3 (2)	C181—C18—C19—C20	1.7 (4)
N22—C6—C7—C71	−179.7 (2)	C17—C18—C19—N24	0.7 (3)
C5—C6—C7—C71	0.9 (4)	C181—C18—C19—N24	−177.5 (2)
C8—C7—C71—C72	−89.4 (3)	N24—C19—C20—C1	1.7 (4)
C6—C7—C71—C72	90.3 (3)	C18—C19—C20—C1	−177.4 (2)
C6—C7—C8—C9	0.3 (3)	N21—C1—C20—C19	−4.1 (4)
C71—C7—C8—C9	−180.0 (2)	C2—C1—C20—C19	175.8 (2)