metal-organic compounds
(1-Methyl-1H-imidazole-κN3)(1-methyl-2-nitrosobenzene-κN)(5,10,15,20-tetraphenylporphyrinato-κ4N)iron(II) dichloromethane monosolvate
aDepartment of Chemistry and Biochemistry, University of Oklahoma, 101 Stephenson Pkwy, Norman, OK 73019, USA
*Correspondence e-mail: grichteraddo@ou.edu
The solvated title compound, [Fe(C44H28N4)(C4H6N2)(C7H7NO)]·CH2Cl2, is a porphyrin complex containing an octahedrally coordinated FeII atom with 1-methylimidazole [Fe—N = 2.0651 (17) Å] and o-nitrosotoluene ligands at the axial positions. The o-nitrosotoluene ligand is N-bound to iron(II) [Fe—N = 1.8406 (18)Å and Fe—N—O = 122.54 (14)°]. The axial N—Fe—N linkage is almost linear, with a bond angle of 177.15 (7)°. One phenyl group of the porphyrin ligand is disordered over two orientations in a 0.710 (3):0.290 (3) ratio. The dichloromethane solvent molecule was severely disordered and its contribution to the scattering was removed with the SQUEEZE routine [van der Sluis & Spek (1990). Acta Cryst. A46, 194–201].
CCDC reference: 981329
Related literature
; Hirota & Itano, 1978; Murayama, 1960; Gibson, 1960; Yi et al., 2013). For the syntheses and crystal structures of related compounds, see: Wang et al. (1996); Godbout et al. (1999); Sohl et al. (2004). For a review on the interactions of C-nitroso compounds with metalloporphyrins, see: Lee et al. (2002). For the preparation of (TPP)FeCl (TPPH2 is 5,10,15,20-tetraphenylporphyrin), see: Adler et al. (1970). For the use of SQUEEZE, see: van der Sluis & Spek (1990).
are known to bind the Fe centers of many heme proteins including the blood protein hemoglobin (Keilin & Hartree, 1943Experimental
Crystal data
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Data collection: SMART (Bruker, 2007); cell SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013; molecular graphics: SHELXL2013; software used to prepare material for publication: SHELXL2013.
Supporting information
CCDC reference: 981329
10.1107/S160053681400083X/hb7178sup1.cif
contains datablocks I, New_Global_Publ_Block. DOI:Structure factors: contains datablock I. DOI: 10.1107/S160053681400083X/hb7178Isup2.hkl
To a Schlenk tube equipped with a magnetic stirrer was added (TPP)FeCl (61 mg, 0.09 mmol) and THF (15 ml). Zn(Hg) (60 mg, 0.9 mmol in Zn) was added and the mixture stirred for 2 h. The resulting solution was filtered into a clean Schlenk tube and the THF removed under vacuum and the residue subsequently dried. The purple (TPP)FeII solid obtained was dissolved in 15 ml of CH2Cl2, treated with 2-nitrosotoluene (50 mg, 0.4 mmol), and stirred for 12 h. The solution was reduced to 5 ml, and 10 ml hexane was added. The resulting solid was collected by filtration. The IR (KBr) spectrum showed the νNO band at 1350 cm-1, comparable with the 1353 cm-1 νNO band observed for (TPP)Fe(PhNO)2 (Wang et al., 1996). The (TPP)Fe(o-tolNO)2 obtained was then treated with 0.5 equivalent of 1-methylimidazole (purchased from Aldrich Chemical Company and used as received) and stirred for 30 min during which time the color of the solution changed from red-purple to brown-green. The solution was filtered and dried in vacuo. The IR (KBr) spectrum of the (TPP)Fe(o-tolNO)(1-MeIm) product showed the νNO band at 1366 cm-1. A suitable purple-needle shaped crystal was grown by slow evaporation of a CH2Cl2-hexane (1:1) solution of the complex at room temperature under N2.
H atoms were located geometrically and treated as riding on their parent atoms with C–H = 0.95 Å for aromatic and 0.98 Å for methyl, and with Uiso(H) = 1.2 (1.5 for methyl) times Ueq(C). Restraints on the 1–2 (e.s.d. = 0.004Å) and 1–3 (e.s.d. = 0.008Å) contacts as well as planarity (e.s.d = 0.008Å) of the disordered phenyl groups were required. The displacement parameters of the disordered atoms were restrained to have similar values along bonded connections (e.s.d. = 0.003Å2).
Nitroso compounds are known to bind the Fe centers of many heme proteins including the blood protein hemoglobin (Keilin & Hartree, 1943; Hirota & Itano, 1978; Murayama, 1960; Gibson, 1960; Yi et al., 2013). The synthetic bis-nitrosoarene iron porphyrin, (TPP)Fe(PhNO)2, was prepared and structurally characterized by X-ray crystallography (Wang et al., 1996). We report the κN3)(1-methyl-2-nitrosobenzene-κN)(5,10,15,20-tetraphenylporphyrinato-κ4N)iron(II) dichloromethane monosolvate compound, (TPP)Fe(o-tolNO)(1-MeIm), (I). For the syntheses and crystal structures of related compounds, see: Wang et al. (1996); Godbout et al. (1999); Sohl et al. (2004). For a review, see: Lee et al. (2002). The molecular structure of (I) is shown in Fig. 1. The Fe—N(por) bond lengths are in the 2.0159 (16)–1.9992 (17) Å range. The Fe—N(1-MeIm) and Fe—N(o-tolNO) bond lengths are 2.0651 (17) and 1.8406 (18) Å, respectively. The axial N—Fe—N linkage shows a near linear geometry with a bond angle of 177.15 (7)°.
of the six-coordinate (1-methyl-1H-imidazole-Nitroso compounds are known to bind the Fe centers of many heme proteins including the blood protein hemoglobin (Keilin & Hartree, 1943; Hirota & Itano, 1978; Murayama, 1960; Gibson, 1960; Yi et al., 2013). For the syntheses and crystal structures of related compounds, see: Wang et al. (1996); Godbout et al. (1999); Sohl et al. (2004). For a review on the interactions of C-nitroso compounds with metalloporphyrins, see: Lee et al. (2002). For the preparation of (TPP)FeCl (TPPH2 is 5,10,15,20-tetraphenylporphyrin), see: Adler et al. (1970). For the use of SQUEEZE, see: van der Sluis & Spek (19901).
Data collection: SMART (Bruker, 2007); cell
SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXL2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: SHELXL2013 (Sheldrick, 2008); software used to prepare material for publication: SHELXL2013 (Sheldrick, 2008).Fig. 1. The molecular structure of (TPP)Fe(o-tolNO)(1-MeIm) with displacement ellipsoids drawn at the 50% probability level. H atoms and the dichloromethane solvent molecule are omitted for clarity. |
[Fe(C44H28N4)(C4H6N2)(C7H7NO)]·CH2Cl2 | Z = 2 |
Mr = 956.72 | F(000) = 992 |
Triclinic, P1 | Dx = 1.357 Mg m−3 |
a = 12.1749 (12) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 13.4571 (13) Å | Cell parameters from 8531 reflections |
c = 15.0439 (15) Å | θ = 2.3–28.3° |
α = 107.450 (2)° | µ = 0.49 mm−1 |
β = 94.800 (2)° | T = 100 K |
γ = 90.987 (2)° | Needle, purple |
V = 2340.8 (4) Å3 | 0.54 × 0.15 × 0.08 mm |
Bruker APEX CCD diffractometer | 8649 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.044 |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | θmax = 28.4°, θmin = 1.4° |
Tmin = 0.779, Tmax = 0.962 | h = −16→16 |
43417 measured reflections | k = −17→17 |
11596 independent reflections | l = −20→20 |
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)] = 0.056 | Hydrogen site location: mixed |
wR(F2) = 0.173 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.117P)2] where P = (Fo2 + 2Fc2)/3 |
11596 reflections | (Δ/σ)max = 0.001 |
632 parameters | Δρmax = 1.12 e Å−3 |
353 restraints | Δρmin = −0.44 e Å−3 |
[Fe(C44H28N4)(C4H6N2)(C7H7NO)]·CH2Cl2 | γ = 90.987 (2)° |
Mr = 956.72 | V = 2340.8 (4) Å3 |
Triclinic, P1 | Z = 2 |
a = 12.1749 (12) Å | Mo Kα radiation |
b = 13.4571 (13) Å | µ = 0.49 mm−1 |
c = 15.0439 (15) Å | T = 100 K |
α = 107.450 (2)° | 0.54 × 0.15 × 0.08 mm |
β = 94.800 (2)° |
Bruker APEX CCD diffractometer | 11596 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | 8649 reflections with I > 2σ(I) |
Tmin = 0.779, Tmax = 0.962 | Rint = 0.044 |
43417 measured reflections |
R[F2 > 2σ(F2)] = 0.056 | 353 restraints |
wR(F2) = 0.173 | H-atom parameters constrained |
S = 1.00 | Δρmax = 1.12 e Å−3 |
11596 reflections | Δρmin = −0.44 e Å−3 |
632 parameters |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Fe1 | 0.27912 (2) | 0.33446 (2) | 0.73638 (2) | 0.01878 (10) | |
O1 | 0.28119 (13) | 0.22468 (12) | 0.55162 (10) | 0.0307 (3) | |
N1 | 0.32161 (14) | 0.19079 (13) | 0.73360 (11) | 0.0206 (3) | |
N2 | 0.42828 (13) | 0.36153 (12) | 0.69803 (11) | 0.0187 (3) | |
N3 | 0.23961 (13) | 0.48146 (13) | 0.74402 (11) | 0.0191 (3) | |
N4 | 0.13367 (14) | 0.31196 (13) | 0.78213 (11) | 0.0212 (3) | |
N5 | 0.33989 (13) | 0.38736 (13) | 0.87552 (12) | 0.0213 (3) | |
N6 | 0.35960 (14) | 0.48117 (14) | 1.02497 (12) | 0.0231 (4) | |
N7 | 0.22530 (14) | 0.28062 (13) | 0.61269 (12) | 0.0249 (4) | |
C1 | 0.25682 (18) | 0.11657 (15) | 0.75314 (15) | 0.0252 (4) | |
C2 | 0.31521 (18) | 0.02104 (16) | 0.73937 (16) | 0.0274 (5) | |
H2 | 0.2887 | −0.0417 | 0.7483 | 0.033* | |
C3 | 0.41421 (18) | 0.03794 (16) | 0.71148 (15) | 0.0260 (4) | |
H3 | 0.4707 | −0.0106 | 0.6973 | 0.031* | |
C4 | 0.41839 (17) | 0.14389 (15) | 0.70712 (13) | 0.0208 (4) | |
C5 | 0.50755 (16) | 0.18962 (15) | 0.67927 (13) | 0.0198 (4) | |
C6 | 0.51086 (16) | 0.29226 (15) | 0.67560 (13) | 0.0190 (4) | |
C7 | 0.60498 (17) | 0.34018 (15) | 0.64984 (14) | 0.0216 (4) | |
H7 | 0.6720 | 0.3084 | 0.6318 | 0.026* | |
C8 | 0.57892 (16) | 0.43990 (15) | 0.65640 (13) | 0.0204 (4) | |
H8 | 0.6244 | 0.4912 | 0.6438 | 0.024* | |
C9 | 0.46861 (16) | 0.45290 (15) | 0.68625 (13) | 0.0179 (4) | |
C10 | 0.41329 (16) | 0.54554 (14) | 0.70135 (13) | 0.0180 (4) | |
C11 | 0.30580 (16) | 0.55733 (15) | 0.72738 (13) | 0.0194 (4) | |
C12 | 0.24626 (17) | 0.65065 (16) | 0.73692 (15) | 0.0247 (4) | |
H12 | 0.2728 | 0.7132 | 0.7275 | 0.030* | |
C13 | 0.14504 (17) | 0.63272 (16) | 0.76183 (15) | 0.0246 (4) | |
H13 | 0.0876 | 0.6805 | 0.7739 | 0.029* | |
C14 | 0.14132 (16) | 0.52730 (15) | 0.76648 (13) | 0.0207 (4) | |
C15 | 0.05222 (16) | 0.48178 (16) | 0.79508 (13) | 0.0214 (4) | |
C16 | 0.05021 (16) | 0.38091 (16) | 0.80217 (14) | 0.0221 (4) | |
C17 | −0.04337 (18) | 0.33265 (17) | 0.82872 (16) | 0.0306 (5) | |
H17 | −0.1110 | 0.3639 | 0.8457 | 0.037* | |
C18 | −0.01645 (19) | 0.23438 (17) | 0.82475 (17) | 0.0330 (5) | |
H18 | −0.0617 | 0.1835 | 0.8383 | 0.040* | |
C19 | 0.09441 (17) | 0.22134 (16) | 0.79584 (15) | 0.0251 (4) | |
C20 | 0.15014 (17) | 0.12930 (16) | 0.78117 (15) | 0.0280 (5) | |
C21 | 0.60513 (16) | 0.12444 (15) | 0.65022 (14) | 0.0218 (4) | |
C22 | 0.67985 (18) | 0.10442 (16) | 0.71722 (15) | 0.0278 (5) | |
H22 | 0.6699 | 0.1330 | 0.7818 | 0.033* | |
C23 | 0.76924 (18) | 0.04261 (17) | 0.69030 (17) | 0.0304 (5) | |
H23 | 0.8199 | 0.0294 | 0.7366 | 0.036* | |
C24 | 0.78457 (18) | 0.00025 (17) | 0.59626 (17) | 0.0314 (5) | |
H24 | 0.8454 | −0.0420 | 0.5780 | 0.038* | |
C25 | 0.71019 (19) | 0.02015 (17) | 0.52882 (16) | 0.0297 (5) | |
H25 | 0.7202 | −0.0087 | 0.4643 | 0.036* | |
C26 | 0.62130 (18) | 0.08223 (16) | 0.55575 (15) | 0.0258 (4) | |
H26 | 0.5712 | 0.0960 | 0.5094 | 0.031* | |
C27 | 0.47130 (16) | 0.63681 (14) | 0.68413 (14) | 0.0197 (4) | |
C28 | 0.51245 (18) | 0.72280 (16) | 0.75862 (15) | 0.0252 (4) | |
H28 | 0.5013 | 0.7253 | 0.8210 | 0.030* | |
C29 | 0.57002 (19) | 0.80518 (17) | 0.74160 (17) | 0.0305 (5) | |
H29 | 0.5985 | 0.8631 | 0.7925 | 0.037* | |
C30 | 0.58573 (18) | 0.80257 (16) | 0.65035 (17) | 0.0298 (5) | |
H30 | 0.6255 | 0.8581 | 0.6388 | 0.036* | |
C31 | 0.54309 (19) | 0.71878 (18) | 0.57686 (16) | 0.0310 (5) | |
H31 | 0.5529 | 0.7169 | 0.5144 | 0.037* | |
C32 | 0.48549 (18) | 0.63668 (16) | 0.59382 (15) | 0.0267 (4) | |
H32 | 0.4556 | 0.5798 | 0.5425 | 0.032* | |
C33 | −0.04463 (16) | 0.54815 (16) | 0.82277 (14) | 0.0233 (4) | |
C34 | −0.05881 (18) | 0.59595 (17) | 0.91690 (15) | 0.0272 (4) | |
H34 | −0.0092 | 0.5831 | 0.9640 | 0.033* | |
C35 | −0.14542 (18) | 0.66269 (17) | 0.94277 (16) | 0.0296 (5) | |
H35 | −0.1544 | 0.6947 | 1.0071 | 0.035* | |
C36 | −0.21769 (17) | 0.68183 (16) | 0.87467 (16) | 0.0287 (5) | |
H36 | −0.2754 | 0.7283 | 0.8921 | 0.034* | |
C37 | −0.20617 (17) | 0.63337 (17) | 0.78090 (16) | 0.0285 (5) | |
H37 | −0.2570 | 0.6457 | 0.7343 | 0.034* | |
C38 | −0.12001 (17) | 0.56641 (17) | 0.75463 (15) | 0.0269 (4) | |
H38 | −0.1127 | 0.5332 | 0.6902 | 0.032* | |
C39 | 0.08236 (15) | 0.03490 (17) | 0.78418 (19) | 0.0339 (6) | 0.710 (3) |
C40 | 0.0490 (2) | 0.0299 (2) | 0.8685 (2) | 0.0446 (6) | 0.710 (3) |
H40 | 0.0687 | 0.0854 | 0.9241 | 0.054* | 0.710 (3) |
C41 | −0.0130 (3) | −0.0561 (2) | 0.8718 (2) | 0.0488 (7) | 0.710 (3) |
H41 | −0.0361 | −0.0592 | 0.9297 | 0.059* | 0.710 (3) |
C42 | −0.0411 (3) | −0.1370 (2) | 0.7912 (2) | 0.0431 (7) | 0.710 (3) |
H42 | −0.0829 | −0.1961 | 0.7938 | 0.052* | 0.710 (3) |
C43 | −0.0086 (2) | −0.1324 (2) | 0.7066 (2) | 0.0386 (6) | 0.710 (3) |
H43 | −0.0288 | −0.1879 | 0.6510 | 0.046* | 0.710 (3) |
C44 | 0.0535 (2) | −0.04654 (19) | 0.7032 (2) | 0.0327 (6) | 0.710 (3) |
H44 | 0.0764 | −0.0435 | 0.6452 | 0.039* | 0.710 (3) |
C39' | 0.1044 (3) | 0.0379 (3) | 0.8102 (4) | 0.0386 (8) | 0.290 (3) |
C40' | 0.1286 (5) | 0.0217 (4) | 0.8966 (4) | 0.0430 (8) | 0.290 (3) |
H40' | 0.1770 | 0.0698 | 0.9431 | 0.052* | 0.290 (3) |
C41' | 0.0830 (6) | −0.0638 (5) | 0.9157 (4) | 0.0474 (9) | 0.290 (3) |
H41' | 0.1013 | −0.0749 | 0.9746 | 0.057* | 0.290 (3) |
C42' | 0.0109 (5) | −0.1329 (4) | 0.8489 (5) | 0.0452 (9) | 0.290 (3) |
H42' | −0.0226 | −0.1902 | 0.8627 | 0.054* | 0.290 (3) |
C43' | −0.0128 (5) | −0.1189 (5) | 0.7619 (5) | 0.0414 (8) | 0.290 (3) |
H43' | −0.0609 | −0.1674 | 0.7154 | 0.050* | 0.290 (3) |
C44' | 0.0340 (5) | −0.0336 (5) | 0.7431 (4) | 0.0393 (7) | 0.290 (3) |
H44' | 0.0177 | −0.0240 | 0.6834 | 0.047* | 0.290 (3) |
C45 | 0.31048 (16) | 0.47243 (16) | 0.93911 (14) | 0.0224 (4) | |
H45 | 0.2610 | 0.5210 | 0.9257 | 0.027* | |
C46 | 0.42338 (17) | 0.39635 (17) | 1.01665 (15) | 0.0257 (4) | |
H46 | 0.4677 | 0.3807 | 1.0654 | 0.031* | |
C47 | 0.41053 (16) | 0.33881 (16) | 0.92439 (14) | 0.0240 (4) | |
H47 | 0.4449 | 0.2752 | 0.8979 | 0.029* | |
C48 | 0.34210 (18) | 0.56187 (18) | 1.11202 (15) | 0.0293 (5) | |
H48A | 0.3083 | 0.6213 | 1.0974 | 0.044* | |
H48B | 0.4131 | 0.5848 | 1.1491 | 0.044* | |
H48C | 0.2932 | 0.5335 | 1.1479 | 0.044* | |
C49 | 0.11486 (18) | 0.29409 (18) | 0.57262 (15) | 0.0296 (5) | |
C50 | 0.1022 (2) | 0.36033 (19) | 0.51683 (16) | 0.0344 (5) | |
C51 | −0.0039 (2) | 0.3676 (2) | 0.4774 (2) | 0.0464 (7) | |
H51 | −0.0151 | 0.4120 | 0.4391 | 0.056* | |
C52 | −0.0943 (2) | 0.3112 (2) | 0.4925 (2) | 0.0501 (7) | |
H52 | −0.1659 | 0.3190 | 0.4658 | 0.060* | |
C53 | −0.0798 (2) | 0.2441 (2) | 0.54629 (19) | 0.0438 (6) | |
H53 | −0.1409 | 0.2050 | 0.5560 | 0.053* | |
C54 | 0.0256 (2) | 0.23475 (19) | 0.58583 (17) | 0.0350 (5) | |
H54 | 0.0369 | 0.1880 | 0.6218 | 0.042* | |
C55 | 0.2007 (2) | 0.4181 (2) | 0.49696 (18) | 0.0395 (6) | |
H55A | 0.2423 | 0.3694 | 0.4511 | 0.059* | |
H55B | 0.2484 | 0.4483 | 0.5551 | 0.059* | |
H55C | 0.1750 | 0.4738 | 0.4719 | 0.059* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Fe1 | 0.02012 (16) | 0.01441 (15) | 0.02301 (16) | −0.00056 (11) | 0.00536 (11) | 0.00665 (11) |
O1 | 0.0399 (9) | 0.0239 (8) | 0.0262 (7) | 0.0005 (7) | 0.0085 (7) | 0.0030 (6) |
N1 | 0.0235 (8) | 0.0148 (8) | 0.0236 (8) | −0.0022 (6) | 0.0039 (7) | 0.0057 (6) |
N2 | 0.0221 (8) | 0.0136 (7) | 0.0201 (8) | 0.0002 (6) | 0.0014 (6) | 0.0047 (6) |
N3 | 0.0195 (8) | 0.0184 (8) | 0.0203 (8) | 0.0002 (6) | 0.0026 (6) | 0.0070 (6) |
N4 | 0.0241 (8) | 0.0170 (8) | 0.0210 (8) | −0.0035 (6) | 0.0020 (7) | 0.0039 (6) |
N5 | 0.0200 (8) | 0.0183 (8) | 0.0275 (9) | −0.0019 (6) | 0.0051 (7) | 0.0091 (7) |
N6 | 0.0206 (8) | 0.0251 (9) | 0.0234 (8) | −0.0040 (7) | 0.0029 (7) | 0.0073 (7) |
N7 | 0.0256 (9) | 0.0180 (8) | 0.0302 (9) | −0.0028 (7) | 0.0065 (7) | 0.0051 (7) |
C1 | 0.0319 (11) | 0.0155 (9) | 0.0283 (10) | −0.0027 (8) | 0.0071 (9) | 0.0059 (8) |
C2 | 0.0339 (12) | 0.0158 (10) | 0.0353 (11) | −0.0008 (8) | 0.0058 (9) | 0.0112 (9) |
C3 | 0.0306 (11) | 0.0144 (9) | 0.0332 (11) | −0.0001 (8) | 0.0018 (9) | 0.0079 (8) |
C4 | 0.0265 (10) | 0.0140 (9) | 0.0207 (9) | −0.0011 (7) | 0.0008 (8) | 0.0038 (7) |
C5 | 0.0226 (9) | 0.0149 (9) | 0.0201 (9) | 0.0000 (7) | 0.0000 (7) | 0.0029 (7) |
C6 | 0.0205 (9) | 0.0167 (9) | 0.0197 (9) | −0.0004 (7) | 0.0015 (7) | 0.0053 (7) |
C7 | 0.0222 (10) | 0.0167 (9) | 0.0254 (10) | −0.0007 (7) | 0.0051 (8) | 0.0050 (8) |
C8 | 0.0202 (9) | 0.0172 (9) | 0.0235 (9) | −0.0010 (7) | 0.0037 (8) | 0.0052 (8) |
C9 | 0.0203 (9) | 0.0157 (9) | 0.0172 (8) | −0.0022 (7) | 0.0010 (7) | 0.0043 (7) |
C10 | 0.0218 (9) | 0.0148 (9) | 0.0172 (8) | −0.0015 (7) | 0.0020 (7) | 0.0045 (7) |
C11 | 0.0238 (10) | 0.0168 (9) | 0.0180 (9) | 0.0007 (7) | 0.0021 (7) | 0.0056 (7) |
C12 | 0.0248 (10) | 0.0211 (10) | 0.0305 (10) | 0.0027 (8) | 0.0057 (8) | 0.0105 (8) |
C13 | 0.0253 (10) | 0.0214 (10) | 0.0299 (10) | 0.0056 (8) | 0.0053 (8) | 0.0110 (8) |
C14 | 0.0217 (10) | 0.0192 (9) | 0.0215 (9) | 0.0028 (7) | 0.0000 (8) | 0.0073 (8) |
C15 | 0.0180 (9) | 0.0242 (10) | 0.0194 (9) | 0.0020 (8) | 0.0005 (7) | 0.0031 (8) |
C16 | 0.0186 (9) | 0.0225 (10) | 0.0222 (9) | −0.0027 (8) | 0.0027 (8) | 0.0023 (8) |
C17 | 0.0244 (11) | 0.0263 (11) | 0.0369 (12) | −0.0063 (9) | 0.0106 (9) | 0.0016 (9) |
C18 | 0.0296 (11) | 0.0222 (11) | 0.0431 (13) | −0.0070 (9) | 0.0171 (10) | 0.0002 (9) |
C19 | 0.0263 (10) | 0.0190 (10) | 0.0280 (10) | −0.0070 (8) | 0.0075 (8) | 0.0033 (8) |
C20 | 0.0361 (12) | 0.0168 (10) | 0.0299 (11) | −0.0071 (9) | 0.0098 (9) | 0.0040 (8) |
C21 | 0.0222 (10) | 0.0125 (9) | 0.0303 (10) | −0.0010 (7) | 0.0027 (8) | 0.0061 (8) |
C22 | 0.0293 (11) | 0.0213 (10) | 0.0295 (11) | 0.0019 (8) | −0.0021 (9) | 0.0040 (8) |
C23 | 0.0257 (11) | 0.0215 (10) | 0.0401 (12) | −0.0002 (8) | −0.0058 (9) | 0.0060 (9) |
C24 | 0.0241 (11) | 0.0203 (10) | 0.0462 (13) | 0.0039 (8) | 0.0046 (10) | 0.0040 (10) |
C25 | 0.0317 (11) | 0.0222 (11) | 0.0326 (11) | 0.0030 (9) | 0.0065 (9) | 0.0032 (9) |
C26 | 0.0272 (11) | 0.0208 (10) | 0.0284 (10) | 0.0014 (8) | 0.0018 (9) | 0.0060 (8) |
C27 | 0.0208 (9) | 0.0135 (9) | 0.0261 (10) | 0.0011 (7) | 0.0047 (8) | 0.0071 (7) |
C28 | 0.0324 (11) | 0.0179 (10) | 0.0266 (10) | 0.0003 (8) | 0.0008 (9) | 0.0091 (8) |
C29 | 0.0333 (12) | 0.0163 (10) | 0.0396 (12) | −0.0045 (9) | −0.0050 (10) | 0.0077 (9) |
C30 | 0.0291 (11) | 0.0172 (10) | 0.0465 (13) | −0.0027 (8) | 0.0046 (10) | 0.0147 (9) |
C31 | 0.0384 (13) | 0.0277 (11) | 0.0317 (11) | −0.0008 (9) | 0.0102 (10) | 0.0145 (9) |
C32 | 0.0345 (11) | 0.0190 (10) | 0.0256 (10) | −0.0049 (8) | 0.0055 (9) | 0.0047 (8) |
C33 | 0.0200 (9) | 0.0225 (10) | 0.0262 (10) | −0.0005 (8) | 0.0036 (8) | 0.0051 (8) |
C34 | 0.0269 (11) | 0.0274 (11) | 0.0259 (10) | 0.0007 (9) | 0.0042 (9) | 0.0053 (9) |
C35 | 0.0277 (11) | 0.0270 (11) | 0.0304 (11) | −0.0017 (9) | 0.0106 (9) | 0.0012 (9) |
C36 | 0.0219 (10) | 0.0204 (10) | 0.0443 (13) | 0.0012 (8) | 0.0107 (9) | 0.0085 (9) |
C37 | 0.0210 (10) | 0.0266 (11) | 0.0371 (12) | 0.0006 (8) | 0.0003 (9) | 0.0089 (9) |
C38 | 0.0241 (10) | 0.0287 (11) | 0.0261 (10) | 0.0025 (8) | 0.0025 (8) | 0.0053 (9) |
C39 | 0.0362 (12) | 0.0202 (10) | 0.0475 (14) | −0.0028 (10) | 0.0134 (11) | 0.0115 (10) |
C40 | 0.0508 (13) | 0.0324 (11) | 0.0524 (13) | −0.0122 (11) | 0.0136 (12) | 0.0136 (11) |
C41 | 0.0549 (13) | 0.0363 (12) | 0.0594 (14) | −0.0140 (11) | 0.0163 (12) | 0.0188 (11) |
C42 | 0.0425 (13) | 0.0271 (11) | 0.0641 (15) | −0.0055 (11) | 0.0141 (12) | 0.0184 (11) |
C43 | 0.0350 (13) | 0.0198 (11) | 0.0596 (15) | −0.0010 (10) | 0.0105 (12) | 0.0088 (12) |
C44 | 0.0293 (12) | 0.0187 (10) | 0.0510 (14) | −0.0003 (9) | 0.0112 (11) | 0.0098 (10) |
C39' | 0.0400 (15) | 0.0239 (14) | 0.0525 (16) | −0.0055 (13) | 0.0152 (14) | 0.0101 (13) |
C40' | 0.0490 (16) | 0.0297 (14) | 0.0531 (16) | −0.0082 (14) | 0.0167 (15) | 0.0139 (14) |
C41' | 0.0541 (17) | 0.0339 (16) | 0.0570 (17) | −0.0093 (16) | 0.0170 (16) | 0.0154 (15) |
C42' | 0.0477 (17) | 0.0308 (16) | 0.0609 (18) | −0.0076 (15) | 0.0172 (16) | 0.0169 (15) |
C43' | 0.0413 (15) | 0.0258 (13) | 0.0603 (16) | −0.0052 (12) | 0.0136 (14) | 0.0156 (14) |
C44' | 0.0388 (13) | 0.0240 (12) | 0.0568 (15) | −0.0051 (12) | 0.0115 (13) | 0.0133 (12) |
C45 | 0.0204 (9) | 0.0237 (10) | 0.0246 (10) | −0.0008 (8) | 0.0037 (8) | 0.0093 (8) |
C46 | 0.0225 (10) | 0.0301 (11) | 0.0282 (10) | −0.0010 (8) | 0.0022 (8) | 0.0146 (9) |
C47 | 0.0214 (10) | 0.0231 (10) | 0.0303 (11) | 0.0012 (8) | 0.0059 (8) | 0.0116 (9) |
C48 | 0.0293 (11) | 0.0315 (12) | 0.0242 (10) | −0.0047 (9) | 0.0036 (9) | 0.0042 (9) |
C49 | 0.0302 (11) | 0.0294 (11) | 0.0261 (10) | −0.0020 (9) | −0.0002 (9) | 0.0043 (9) |
C50 | 0.0375 (13) | 0.0360 (13) | 0.0301 (11) | −0.0008 (10) | −0.0006 (10) | 0.0117 (10) |
C51 | 0.0398 (14) | 0.0577 (17) | 0.0471 (15) | −0.0045 (13) | −0.0084 (12) | 0.0275 (14) |
C52 | 0.0325 (14) | 0.0608 (19) | 0.0584 (18) | −0.0022 (13) | −0.0091 (12) | 0.0238 (15) |
C53 | 0.0361 (14) | 0.0482 (16) | 0.0430 (14) | −0.0152 (12) | −0.0041 (11) | 0.0108 (12) |
C54 | 0.0352 (12) | 0.0334 (13) | 0.0340 (12) | −0.0082 (10) | 0.0006 (10) | 0.0077 (10) |
C55 | 0.0421 (14) | 0.0446 (15) | 0.0370 (13) | −0.0018 (11) | −0.0013 (11) | 0.0220 (11) |
Fe1—N7 | 1.8406 (18) | C27—C32 | 1.383 (3) |
Fe1—N1 | 1.9992 (17) | C27—C28 | 1.398 (3) |
Fe1—N4 | 2.0030 (17) | C28—C29 | 1.400 (3) |
Fe1—N2 | 2.0105 (16) | C28—H28 | 0.9500 |
Fe1—N3 | 2.0159 (16) | C29—C30 | 1.392 (3) |
Fe1—N5 | 2.0651 (17) | C29—H29 | 0.9500 |
O1—N7 | 1.257 (2) | C30—C31 | 1.378 (3) |
N1—C1 | 1.376 (2) | C30—H30 | 0.9500 |
N1—C4 | 1.378 (3) | C31—C32 | 1.396 (3) |
N2—C6 | 1.376 (2) | C31—H31 | 0.9500 |
N2—C9 | 1.382 (2) | C32—H32 | 0.9500 |
N3—C14 | 1.377 (2) | C33—C34 | 1.395 (3) |
N3—C11 | 1.383 (2) | C33—C38 | 1.398 (3) |
N4—C16 | 1.379 (3) | C34—C35 | 1.401 (3) |
N4—C19 | 1.380 (3) | C34—H34 | 0.9500 |
N5—C45 | 1.330 (3) | C35—C36 | 1.380 (3) |
N5—C47 | 1.381 (3) | C35—H35 | 0.9500 |
N6—C45 | 1.348 (3) | C36—C37 | 1.385 (3) |
N6—C46 | 1.372 (3) | C36—H36 | 0.9500 |
N6—C48 | 1.463 (3) | C37—C38 | 1.399 (3) |
N7—C49 | 1.464 (3) | C37—H37 | 0.9500 |
C1—C20 | 1.396 (3) | C38—H38 | 0.9500 |
C1—C2 | 1.448 (3) | C39—C40 | 1.383 (3) |
C2—C3 | 1.346 (3) | C39—C44 | 1.387 (3) |
C2—H2 | 0.9500 | C40—C41 | 1.387 (3) |
C3—C4 | 1.447 (3) | C40—H40 | 0.9500 |
C3—H3 | 0.9500 | C41—C42 | 1.378 (3) |
C4—C5 | 1.393 (3) | C41—H41 | 0.9500 |
C5—C6 | 1.399 (3) | C42—C43 | 1.382 (3) |
C5—C21 | 1.505 (3) | C42—H42 | 0.9500 |
C6—C7 | 1.441 (3) | C43—C44 | 1.386 (3) |
C7—C8 | 1.361 (3) | C43—H43 | 0.9500 |
C7—H7 | 0.9500 | C44—H44 | 0.9500 |
C8—C9 | 1.448 (3) | C39'—C44' | 1.387 (3) |
C8—H8 | 0.9500 | C39'—C40' | 1.389 (3) |
C9—C10 | 1.394 (3) | C40'—C41' | 1.385 (3) |
C10—C11 | 1.395 (3) | C40'—H40' | 0.9500 |
C10—C27 | 1.505 (3) | C41'—C42' | 1.383 (3) |
C11—C12 | 1.437 (3) | C41'—H41' | 0.9500 |
C12—C13 | 1.356 (3) | C42'—C43' | 1.385 (3) |
C12—H12 | 0.9500 | C42'—H42' | 0.9500 |
C13—C14 | 1.441 (3) | C43'—C44' | 1.386 (3) |
C13—H13 | 0.9500 | C43'—H43' | 0.9500 |
C14—C15 | 1.396 (3) | C44'—H44' | 0.9500 |
C15—C16 | 1.393 (3) | C45—H45 | 0.9500 |
C15—C33 | 1.502 (3) | C46—C47 | 1.366 (3) |
C16—C17 | 1.444 (3) | C46—H46 | 0.9500 |
C17—C18 | 1.353 (3) | C47—H47 | 0.9500 |
C17—H17 | 0.9500 | C48—H48A | 0.9800 |
C18—C19 | 1.450 (3) | C48—H48B | 0.9800 |
C18—H18 | 0.9500 | C48—H48C | 0.9800 |
C19—C20 | 1.390 (3) | C49—C50 | 1.398 (3) |
C20—C39 | 1.517 (3) | C49—C54 | 1.400 (3) |
C20—C39' | 1.534 (4) | C50—C51 | 1.392 (3) |
C21—C22 | 1.391 (3) | C50—C55 | 1.516 (3) |
C21—C26 | 1.396 (3) | C51—C52 | 1.398 (4) |
C22—C23 | 1.394 (3) | C51—H51 | 0.9500 |
C22—H22 | 0.9500 | C52—C53 | 1.387 (4) |
C23—C24 | 1.388 (3) | C52—H52 | 0.9500 |
C23—H23 | 0.9500 | C53—C54 | 1.392 (4) |
C24—C25 | 1.392 (3) | C53—H53 | 0.9500 |
C24—H24 | 0.9500 | C54—H54 | 0.9500 |
C25—C26 | 1.391 (3) | C55—H55A | 0.9800 |
C25—H25 | 0.9500 | C55—H55B | 0.9800 |
C26—H26 | 0.9500 | C55—H55C | 0.9800 |
N7—Fe1—N1 | 88.22 (7) | C25—C26—H26 | 119.7 |
N7—Fe1—N4 | 92.86 (7) | C21—C26—H26 | 119.7 |
N1—Fe1—N4 | 90.81 (7) | C32—C27—C28 | 118.70 (18) |
N7—Fe1—N2 | 90.38 (7) | C32—C27—C10 | 120.36 (18) |
N1—Fe1—N2 | 89.75 (7) | C28—C27—C10 | 120.94 (17) |
N4—Fe1—N2 | 176.73 (6) | C27—C28—C29 | 120.2 (2) |
N7—Fe1—N3 | 93.95 (7) | C27—C28—H28 | 119.9 |
N1—Fe1—N3 | 177.80 (7) | C29—C28—H28 | 119.9 |
N4—Fe1—N3 | 89.48 (7) | C30—C29—C28 | 120.3 (2) |
N2—Fe1—N3 | 89.84 (7) | C30—C29—H29 | 119.9 |
N7—Fe1—N5 | 177.15 (7) | C28—C29—H29 | 119.9 |
N1—Fe1—N5 | 89.01 (7) | C31—C30—C29 | 119.5 (2) |
N4—Fe1—N5 | 86.52 (6) | C31—C30—H30 | 120.3 |
N2—Fe1—N5 | 90.27 (6) | C29—C30—H30 | 120.3 |
N3—Fe1—N5 | 88.83 (7) | C30—C31—C32 | 120.3 (2) |
C1—N1—C4 | 106.02 (16) | C30—C31—H31 | 119.9 |
C1—N1—Fe1 | 126.48 (14) | C32—C31—H31 | 119.9 |
C4—N1—Fe1 | 127.41 (13) | C27—C32—C31 | 121.0 (2) |
C6—N2—C9 | 105.32 (16) | C27—C32—H32 | 119.5 |
C6—N2—Fe1 | 127.36 (13) | C31—C32—H32 | 119.5 |
C9—N2—Fe1 | 127.29 (13) | C34—C33—C38 | 118.70 (19) |
C14—N3—C11 | 105.59 (16) | C34—C33—C15 | 120.68 (18) |
C14—N3—Fe1 | 127.36 (13) | C38—C33—C15 | 120.57 (18) |
C11—N3—Fe1 | 127.05 (13) | C33—C34—C35 | 120.8 (2) |
C16—N4—C19 | 105.71 (17) | C33—C34—H34 | 119.6 |
C16—N4—Fe1 | 127.68 (14) | C35—C34—H34 | 119.6 |
C19—N4—Fe1 | 126.55 (14) | C36—C35—C34 | 119.9 (2) |
C45—N5—C47 | 105.31 (17) | C36—C35—H35 | 120.1 |
C45—N5—Fe1 | 126.23 (14) | C34—C35—H35 | 120.1 |
C47—N5—Fe1 | 128.22 (14) | C35—C36—C37 | 120.1 (2) |
C45—N6—C46 | 107.23 (17) | C35—C36—H36 | 119.9 |
C45—N6—C48 | 126.44 (18) | C37—C36—H36 | 119.9 |
C46—N6—C48 | 126.20 (18) | C36—C37—C38 | 120.2 (2) |
O1—N7—C49 | 111.42 (17) | C36—C37—H37 | 119.9 |
O1—N7—Fe1 | 122.54 (14) | C38—C37—H37 | 119.9 |
C49—N7—Fe1 | 126.03 (14) | C33—C38—C37 | 120.3 (2) |
N1—C1—C20 | 125.95 (19) | C33—C38—H38 | 119.9 |
N1—C1—C2 | 109.86 (18) | C37—C38—H38 | 119.9 |
C20—C1—C2 | 124.18 (19) | C40—C39—C44 | 119.6 (2) |
C3—C2—C1 | 107.11 (18) | C40—C39—C20 | 119.7 (2) |
C3—C2—H2 | 126.4 | C44—C39—C20 | 120.6 (2) |
C1—C2—H2 | 126.4 | C39—C40—C41 | 120.1 (2) |
C2—C3—C4 | 107.19 (19) | C39—C40—H40 | 119.9 |
C2—C3—H3 | 126.4 | C41—C40—H40 | 119.9 |
C4—C3—H3 | 126.4 | C42—C41—C40 | 120.0 (2) |
N1—C4—C5 | 126.01 (18) | C42—C41—H41 | 120.0 |
N1—C4—C3 | 109.82 (17) | C40—C41—H41 | 120.0 |
C5—C4—C3 | 124.17 (19) | C41—C42—C43 | 120.2 (2) |
C4—C5—C6 | 123.69 (18) | C41—C42—H42 | 119.9 |
C4—C5—C21 | 118.14 (17) | C43—C42—H42 | 119.9 |
C6—C5—C21 | 118.17 (17) | C42—C43—C44 | 119.8 (2) |
N2—C6—C5 | 125.63 (18) | C42—C43—H43 | 120.1 |
N2—C6—C7 | 111.00 (16) | C44—C43—H43 | 120.1 |
C5—C6—C7 | 123.34 (18) | C43—C44—C39 | 120.2 (2) |
C8—C7—C6 | 106.51 (17) | C43—C44—H44 | 119.9 |
C8—C7—H7 | 126.7 | C39—C44—H44 | 119.9 |
C6—C7—H7 | 126.7 | C44'—C39'—C40' | 118.7 (3) |
C7—C8—C9 | 106.94 (17) | C44'—C39'—C20 | 115.9 (4) |
C7—C8—H8 | 126.5 | C40'—C39'—C20 | 125.4 (4) |
C9—C8—H8 | 126.5 | C41'—C40'—C39' | 120.8 (3) |
N2—C9—C10 | 125.88 (17) | C41'—C40'—H40' | 119.6 |
N2—C9—C8 | 110.22 (16) | C39'—C40'—H40' | 119.6 |
C10—C9—C8 | 123.90 (17) | C42'—C41'—C40' | 119.7 (3) |
C9—C10—C11 | 124.00 (18) | C42'—C41'—H41' | 120.1 |
C9—C10—C27 | 117.87 (17) | C40'—C41'—H41' | 120.1 |
C11—C10—C27 | 118.07 (17) | C41'—C42'—C43' | 120.2 (3) |
N3—C11—C10 | 125.90 (17) | C41'—C42'—H42' | 119.9 |
N3—C11—C12 | 110.10 (17) | C43'—C42'—H42' | 119.9 |
C10—C11—C12 | 123.95 (18) | C42'—C43'—C44' | 119.6 (3) |
C13—C12—C11 | 107.15 (18) | C42'—C43'—H43' | 120.2 |
C13—C12—H12 | 126.4 | C44'—C43'—H43' | 120.2 |
C11—C12—H12 | 126.4 | C43'—C44'—C39' | 120.9 (3) |
C12—C13—C14 | 106.88 (18) | C43'—C44'—H44' | 119.5 |
C12—C13—H13 | 126.6 | C39'—C44'—H44' | 119.5 |
C14—C13—H13 | 126.6 | N5—C45—N6 | 111.56 (18) |
N3—C14—C15 | 125.67 (18) | N5—C45—H45 | 124.2 |
N3—C14—C13 | 110.25 (17) | N6—C45—H45 | 124.2 |
C15—C14—C13 | 123.99 (18) | C47—C46—N6 | 106.35 (18) |
C16—C15—C14 | 123.85 (18) | C47—C46—H46 | 126.8 |
C16—C15—C33 | 118.98 (18) | N6—C46—H46 | 126.8 |
C14—C15—C33 | 117.14 (18) | C46—C47—N5 | 109.54 (18) |
N4—C16—C15 | 125.80 (18) | C46—C47—H47 | 125.2 |
N4—C16—C17 | 110.35 (18) | N5—C47—H47 | 125.2 |
C15—C16—C17 | 123.81 (19) | N6—C48—H48A | 109.5 |
C18—C17—C16 | 106.94 (19) | N6—C48—H48B | 109.5 |
C18—C17—H17 | 126.5 | H48A—C48—H48B | 109.5 |
C16—C17—H17 | 126.5 | N6—C48—H48C | 109.5 |
C17—C18—C19 | 107.05 (19) | H48A—C48—H48C | 109.5 |
C17—C18—H18 | 126.5 | H48B—C48—H48C | 109.5 |
C19—C18—H18 | 126.5 | C50—C49—C54 | 121.5 (2) |
N4—C19—C20 | 125.71 (19) | C50—C49—N7 | 119.3 (2) |
N4—C19—C18 | 109.94 (19) | C54—C49—N7 | 119.0 (2) |
C20—C19—C18 | 124.31 (19) | C51—C50—C49 | 117.2 (2) |
C19—C20—C1 | 124.37 (19) | C51—C50—C55 | 121.6 (2) |
C19—C20—C39 | 115.73 (15) | C49—C50—C55 | 121.2 (2) |
C1—C20—C39 | 119.39 (15) | C50—C51—C52 | 121.8 (2) |
C19—C20—C39' | 120.97 (16) | C50—C51—H51 | 119.1 |
C1—C20—C39' | 113.99 (16) | C52—C51—H51 | 119.1 |
C22—C21—C26 | 119.05 (19) | C53—C52—C51 | 120.2 (2) |
C22—C21—C5 | 120.38 (18) | C53—C52—H52 | 119.9 |
C26—C21—C5 | 120.57 (18) | C51—C52—H52 | 119.9 |
C21—C22—C23 | 120.4 (2) | C52—C53—C54 | 119.1 (2) |
C21—C22—H22 | 119.8 | C52—C53—H53 | 120.5 |
C23—C22—H22 | 119.8 | C54—C53—H53 | 120.5 |
C24—C23—C22 | 120.3 (2) | C53—C54—C49 | 120.1 (2) |
C24—C23—H23 | 119.8 | C53—C54—H54 | 119.9 |
C22—C23—H23 | 119.8 | C49—C54—H54 | 119.9 |
C23—C24—C25 | 119.6 (2) | C50—C55—H55A | 109.5 |
C23—C24—H24 | 120.2 | C50—C55—H55B | 109.5 |
C25—C24—H24 | 120.2 | H55A—C55—H55B | 109.5 |
C26—C25—C24 | 120.1 (2) | C50—C55—H55C | 109.5 |
C26—C25—H25 | 120.0 | H55A—C55—H55C | 109.5 |
C24—C25—H25 | 120.0 | H55B—C55—H55C | 109.5 |
C25—C26—C21 | 120.6 (2) | ||
N1—Fe1—N7—O1 | −50.99 (16) | N1—C1—C20—C39 | 169.7 (2) |
N4—Fe1—N7—O1 | −141.71 (16) | C2—C1—C20—C39 | −9.6 (3) |
N2—Fe1—N7—O1 | 38.74 (16) | N1—C1—C20—C39' | −172.4 (3) |
N3—Fe1—N7—O1 | 128.61 (16) | C2—C1—C20—C39' | 8.3 (4) |
N1—Fe1—N7—C49 | 127.69 (17) | C4—C5—C21—C22 | −76.4 (2) |
N4—Fe1—N7—C49 | 36.97 (17) | C6—C5—C21—C22 | 104.5 (2) |
N2—Fe1—N7—C49 | −142.57 (17) | C4—C5—C21—C26 | 102.9 (2) |
N3—Fe1—N7—C49 | −52.70 (17) | C6—C5—C21—C26 | −76.3 (2) |
C4—N1—C1—C20 | −178.8 (2) | C26—C21—C22—C23 | −0.3 (3) |
Fe1—N1—C1—C20 | −1.9 (3) | C5—C21—C22—C23 | 178.93 (19) |
C4—N1—C1—C2 | 0.6 (2) | C21—C22—C23—C24 | −0.1 (3) |
Fe1—N1—C1—C2 | 177.43 (14) | C22—C23—C24—C25 | 0.2 (3) |
N1—C1—C2—C3 | −0.2 (2) | C23—C24—C25—C26 | 0.1 (3) |
C20—C1—C2—C3 | 179.2 (2) | C24—C25—C26—C21 | −0.5 (3) |
C1—C2—C3—C4 | −0.3 (2) | C22—C21—C26—C25 | 0.6 (3) |
C1—N1—C4—C5 | 178.72 (19) | C5—C21—C26—C25 | −178.62 (19) |
Fe1—N1—C4—C5 | 1.9 (3) | C9—C10—C27—C32 | 71.9 (2) |
C1—N1—C4—C3 | −0.8 (2) | C11—C10—C27—C32 | −105.4 (2) |
Fe1—N1—C4—C3 | −177.57 (13) | C9—C10—C27—C28 | −107.7 (2) |
C2—C3—C4—N1 | 0.7 (2) | C11—C10—C27—C28 | 75.1 (2) |
C2—C3—C4—C5 | −178.82 (19) | C32—C27—C28—C29 | −2.1 (3) |
N1—C4—C5—C6 | 0.8 (3) | C10—C27—C28—C29 | 177.46 (19) |
C3—C4—C5—C6 | −179.79 (19) | C27—C28—C29—C30 | 0.7 (3) |
N1—C4—C5—C21 | −178.29 (18) | C28—C29—C30—C31 | 0.7 (3) |
C3—C4—C5—C21 | 1.1 (3) | C29—C30—C31—C32 | −0.6 (3) |
C9—N2—C6—C5 | 178.61 (18) | C28—C27—C32—C31 | 2.3 (3) |
Fe1—N2—C6—C5 | −2.9 (3) | C10—C27—C32—C31 | −177.3 (2) |
C9—N2—C6—C7 | 0.4 (2) | C30—C31—C32—C27 | −0.9 (3) |
Fe1—N2—C6—C7 | 178.86 (13) | C16—C15—C33—C34 | 77.4 (3) |
C4—C5—C6—N2 | −0.3 (3) | C14—C15—C33—C34 | −100.5 (2) |
C21—C5—C6—N2 | 178.81 (17) | C16—C15—C33—C38 | −105.0 (2) |
C4—C5—C6—C7 | 177.76 (18) | C14—C15—C33—C38 | 77.1 (3) |
C21—C5—C6—C7 | −3.1 (3) | C38—C33—C34—C35 | −1.3 (3) |
N2—C6—C7—C8 | −0.2 (2) | C15—C33—C34—C35 | 176.3 (2) |
C5—C6—C7—C8 | −178.53 (18) | C33—C34—C35—C36 | −0.1 (3) |
C6—C7—C8—C9 | 0.0 (2) | C34—C35—C36—C37 | 1.4 (3) |
C6—N2—C9—C10 | −179.75 (18) | C35—C36—C37—C38 | −1.3 (3) |
Fe1—N2—C9—C10 | 1.8 (3) | C34—C33—C38—C37 | 1.5 (3) |
C6—N2—C9—C8 | −0.4 (2) | C15—C33—C38—C37 | −176.1 (2) |
Fe1—N2—C9—C8 | −178.86 (12) | C36—C37—C38—C33 | −0.2 (3) |
C7—C8—C9—N2 | 0.2 (2) | C19—C20—C39—C40 | −70.3 (2) |
C7—C8—C9—C10 | 179.63 (18) | C1—C20—C39—C40 | 117.5 (2) |
N2—C9—C10—C11 | −2.7 (3) | C39'—C20—C39—C40 | 42.0 (5) |
C8—C9—C10—C11 | 177.99 (18) | C19—C20—C39—C44 | 109.7 (2) |
N2—C9—C10—C27 | −179.73 (17) | C1—C20—C39—C44 | −62.4 (2) |
C8—C9—C10—C27 | 1.0 (3) | C39'—C20—C39—C44 | −137.9 (5) |
C14—N3—C11—C10 | −179.38 (18) | C44—C39—C40—C41 | −0.1 (2) |
Fe1—N3—C11—C10 | 0.4 (3) | C20—C39—C40—C41 | 179.96 (18) |
C14—N3—C11—C12 | −1.8 (2) | C39—C40—C41—C42 | 0.3 (4) |
Fe1—N3—C11—C12 | 178.00 (13) | C40—C41—C42—C43 | −0.7 (4) |
C9—C10—C11—N3 | 1.6 (3) | C41—C42—C43—C44 | 0.8 (4) |
C27—C10—C11—N3 | 178.59 (17) | C42—C43—C44—C39 | −0.5 (4) |
C9—C10—C11—C12 | −175.72 (19) | C40—C39—C44—C43 | 0.2 (3) |
C27—C10—C11—C12 | 1.3 (3) | C20—C39—C44—C43 | −179.88 (17) |
N3—C11—C12—C13 | 1.6 (2) | C19—C20—C39'—C44' | 89.8 (4) |
C10—C11—C12—C13 | 179.29 (19) | C1—C20—C39'—C44' | −99.1 (3) |
C11—C12—C13—C14 | −0.8 (2) | C39—C20—C39'—C44' | 13.4 (5) |
C11—N3—C14—C15 | −175.27 (18) | C19—C20—C39'—C40' | −90.7 (3) |
Fe1—N3—C14—C15 | 5.0 (3) | C1—C20—C39'—C40' | 80.3 (3) |
C11—N3—C14—C13 | 1.3 (2) | C39—C20—C39'—C40' | −167.1 (5) |
Fe1—N3—C14—C13 | −178.49 (13) | C44'—C39'—C40'—C41' | −0.4 (3) |
C12—C13—C14—N3 | −0.3 (2) | C20—C39'—C40'—C41' | −179.8 (2) |
C12—C13—C14—C15 | 176.31 (19) | C39'—C40'—C41'—C42' | −1.2 (5) |
N3—C14—C15—C16 | −1.9 (3) | C40'—C41'—C42'—C43' | 2.3 (6) |
C13—C14—C15—C16 | −178.01 (19) | C41'—C42'—C43'—C44' | −1.7 (6) |
N3—C14—C15—C33 | 175.84 (18) | C42'—C43'—C44'—C39' | 0.0 (6) |
C13—C14—C15—C33 | −0.3 (3) | C40'—C39'—C44'—C43' | 1.0 (4) |
C19—N4—C16—C15 | −177.98 (19) | C20—C39'—C44'—C43' | −179.5 (3) |
Fe1—N4—C16—C15 | −0.8 (3) | C47—N5—C45—N6 | 0.9 (2) |
C19—N4—C16—C17 | −0.2 (2) | Fe1—N5—C45—N6 | 175.57 (12) |
Fe1—N4—C16—C17 | 177.06 (14) | C46—N6—C45—N5 | −0.7 (2) |
C14—C15—C16—N4 | −0.3 (3) | C48—N6—C45—N5 | −176.69 (18) |
C33—C15—C16—N4 | −178.01 (18) | C45—N6—C46—C47 | 0.3 (2) |
C14—C15—C16—C17 | −177.84 (19) | C48—N6—C46—C47 | 176.25 (18) |
C33—C15—C16—C17 | 4.5 (3) | N6—C46—C47—N5 | 0.3 (2) |
N4—C16—C17—C18 | 0.0 (2) | C45—N5—C47—C46 | −0.7 (2) |
C15—C16—C17—C18 | 177.9 (2) | Fe1—N5—C47—C46 | −175.24 (13) |
C16—C17—C18—C19 | 0.1 (3) | O1—N7—C49—C50 | −74.2 (2) |
C16—N4—C19—C20 | 178.1 (2) | Fe1—N7—C49—C50 | 107.0 (2) |
Fe1—N4—C19—C20 | 0.8 (3) | O1—N7—C49—C54 | 101.4 (2) |
C16—N4—C19—C18 | 0.2 (2) | Fe1—N7—C49—C54 | −77.4 (2) |
Fe1—N4—C19—C18 | −177.01 (14) | C54—C49—C50—C51 | 2.1 (4) |
C17—C18—C19—N4 | −0.2 (3) | N7—C49—C50—C51 | 177.6 (2) |
C17—C18—C19—C20 | −178.1 (2) | C54—C49—C50—C55 | −175.3 (2) |
N4—C19—C20—C1 | 2.3 (4) | N7—C49—C50—C55 | 0.2 (3) |
C18—C19—C20—C1 | 179.9 (2) | C49—C50—C51—C52 | 0.0 (4) |
N4—C19—C20—C39 | −169.4 (2) | C55—C50—C51—C52 | 177.4 (3) |
C18—C19—C20—C39 | 8.1 (3) | C50—C51—C52—C53 | −1.4 (5) |
N4—C19—C20—C39' | 172.4 (3) | C51—C52—C53—C54 | 0.8 (4) |
C18—C19—C20—C39' | −10.1 (4) | C52—C53—C54—C49 | 1.2 (4) |
N1—C1—C20—C19 | −1.7 (4) | C50—C49—C54—C53 | −2.7 (4) |
C2—C1—C20—C19 | 179.0 (2) | N7—C49—C54—C53 | −178.3 (2) |
Fe1—N7 | 1.8406 (18) | Fe1—N2 | 2.0105 (16) |
Fe1—N1 | 1.9992 (17) | Fe1—N3 | 2.0159 (16) |
Fe1—N4 | 2.0030 (17) | Fe1—N5 | 2.0651 (17) |
Acknowledgements
The authors wish to thank the National Science Foundation (CHE-1213674 and CHE-0130835) and the University of Oklahoma for funds to support this research and to acquire the diffractometer and computers used in this work.
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Nitroso compounds are known to bind the Fe centers of many heme proteins including the blood protein hemoglobin (Keilin & Hartree, 1943; Hirota & Itano, 1978; Murayama, 1960; Gibson, 1960; Yi et al., 2013). The synthetic bis-nitrosoarene iron porphyrin, (TPP)Fe(PhNO)2, was prepared and structurally characterized by X-ray crystallography (Wang et al., 1996). We report the crystal structure of the six-coordinate (1-methyl-1H-imidazole-κN3)(1-methyl-2-nitrosobenzene-κN)(5,10,15,20-tetraphenylporphyrinato-κ4N)iron(II) dichloromethane monosolvate compound, (TPP)Fe(o-tolNO)(1-MeIm), (I). For the syntheses and crystal structures of related compounds, see: Wang et al. (1996); Godbout et al. (1999); Sohl et al. (2004). For a review, see: Lee et al. (2002). The molecular structure of (I) is shown in Fig. 1. The Fe—N(por) bond lengths are in the 2.0159 (16)–1.9992 (17) Å range. The Fe—N(1-MeIm) and Fe—N(o-tolNO) bond lengths are 2.0651 (17) and 1.8406 (18) Å, respectively. The axial N—Fe—N linkage shows a near linear geometry with a bond angle of 177.15 (7)°.