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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 71| Part 2| February 2015| Pages m42-m43
doi:10.1107/S205698901500153X

Crystal structure of chlorido­{5,10,15,20-tetra­kis­[2-(2,2-di­methyl­propanamido)­phen­yl]porphyrinato-κ4N}iron(III)

Dennis Awasabisah,a* Douglas R. Powella and George B. Richter-Addoa

aDepartment of Chemistry and Biochemistry, University of Oklahoma, 101 Stephenson Pkwy, Norman, OK 73019, USA
*Correspondence e-mail: dawas@ou.edu

Edited by E. R. T. Tiekink, University of Malaya, Malaysia (Received 2 January 2015; accepted 23 January 2015; online 31 January 2015)

The title compound, [Fe(C64H64N8O4)Cl], is a five-coordinate square-pyramidal porphyrin complex with a chloride ion in the axial position, being coordinated from the protected side of the porphyrin; the FeIII atom is displaced by 0.474 (5) Å from the 24-atom mean plane of the porphyrin core towards the chloride. The porphyrin moiety is a `picket-fence' 5,10,15,20-tetra­kis­[2-(2,2-di­methyl­propanamido)­phen­yl]porph­yrinate (por) group. The Fe—Cl bond length is 2.221 (2) Å and the Fe—N(por) bond lengths are in the range 2.043 (5)–2.063 (5) Å. The supra­molecular architecture of the crystal is sustained by C—H⋯O inter­actions between the pyrrolic and phenyl H atoms of one mol­ecule and the carbonyl O atoms of the 2,2-di­methyl­propanamido groups of adjacent mol­ecules. The methyl groups of three of the four tert-butyl substituents exhibited rotational disorder over two positions. The investigated crystal was twinned by a twofold rotation about the (001) axis with a refined twin ratio of 0.4086 (16).

CCDC reference: 1045127

1. Related literature

For the synthesis of (TpivPP)FeCl (piv = ortho-pivalamido), see: Collman et al. (1975[Collman, J. P., Gagne, R. R., Reed, C. A., Halbert, T. R., Lang, G. & Robinson, W. T. (1975). J. Am. Chem. Soc. 97, 1427-1439.]). For the crystal structures of other neutral and anionic (TpivPP)FeCl complexes, see: Dhifet et al. (2011[Dhifet, M., Belkhiria, M. S., Daran, J.-C. & Nasri, H. (2011). Acta Cryst. E67, m460-m461.]); Schappacher et al. (1983[Schappacher, M., Ricard, L., Weiss, R., Montiel-Montoya, R., Gonser, U., Bill, E. & Trautwein, A. (1983). Inorg. Chim. Acta, 78, L9-L12.]). For related synthetic applications of the title compound, see: Cheng et al. (2000[Cheng, L., Khan, M. A., Richter-Addo, G. B. & Powell, D. R. (2000). Chem. Commun. pp. 2301-2302.]); Nasri et al. (1997[Nasri, H., Ellison, M. K., Chen, S., Huynh, B. H. & Scheidt, W. R. (1997). J. Am. Chem. Soc. 119, 6274-6283.]); Bominaar et al. (1992[Bominaar, E. L., Ding, X. Q., Gismelseed, A., Bill, E., Winkler, H., Trautwein, A. X., Nasri, H., Fischer, J. & Weiss, R. (1992). J. Am. Chem. Soc. 31, 1845-1854.]); Gismelseed et al. (1990[Gismelseed, A., Bominaar, E. L., Bill, E., Trautwein, A. X., Winkler, H., Nasri, H., Doppelt, P., Mandon, D., Fischer, J. & Weiss, R. (1990). Inorg. Chem. 29, 2741-2749.]).

[Scheme 1]

2. Experimental

2.1. Crystal data

  • [Fe(C64H64N8O4)Cl]

  • Mr = 1100.53

  • Monoclinic, P 21 /n

  • a = 17.763 (3) Å

  • b = 17.652 (3) Å

  • c = 20.145 (4) Å

  • β = 110.570 (4)°

  • V = 5913.8 (18) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.35 mm−1

  • T = 100 K

  • 0.41 × 0.24 × 0.11 mm

2.2. Data collection

  • Bruker APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2002[Bruker (2002). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.869, Tmax = 0.962

  • 69995 measured reflections

  • 18970 independent reflections

  • 9442 reflections with I > 2σ(I)

  • Rint = 0.077

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.092

  • wR(F2) = 0.280

  • S = 1.01

  • 18970 reflections

  • 788 parameters

  • 279 restraints

  • H-atom parameters constrained

  • Δρmax = 1.25 e Å−3

  • Δρmin = −0.45 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C2—H2⋯O1i 0.95 2.43 3.310 (8) 154
C7—H7⋯O2ii 0.95 2.35 3.228 (8) 154
C12—H12⋯O3iii 0.95 2.30 3.223 (8) 163
C17—H17⋯O4iv 0.95 2.32 3.251 (8) 168
C25—H25⋯O1 0.95 2.29 2.884 (12) 120
C36—H36⋯O2 0.95 2.34 2.932 (11) 120
C47—H47⋯O3 0.95 2.24 2.847 (11) 121
C58—H58⋯O4 0.95 2.32 2.909 (11) 119
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+1, -y, -z+1; (iii) -x, -y, -z+1; (iv) -x, -y+1, -z+1.

Data collection: SMART (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]); molecular graphics: XP in SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL2014.

Supporting information

CCDC reference: 1045127

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S205698901500153X/tk5357sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S205698901500153X/tk5357Isup2.hkl

checkCIF report


Comment top

The iron(III) porphyrin complex (TpivPP)FeCl has been used as a precursor for the preparation of several (TpivPP)Fe derivatives in our laboratory (Cheng et al., 2000) and those of several research groups (Nasri et al., 1997; Bominaar et al., 1992; Gismelseed et al., 1990). The molecular structure of the title compound is shown in Fig. 1. The complex (TpivPP)FeCl is square pyramidal and has the chloride atom bonded to iron at the axial position. The chloride ion is coordinated at the protecting 2,2-dimethylpropanamido side of the porphyrin, in contrast to a similar structure reported (Dhifet et al., 2011) where the chloride ligand was on the opposite side of the protecting group. The Fe–Cl bond length is 2.221 (2) Å and the Fe–N(por) bond lengths are in the 2.043 (5)-2.063 (5) Å range. The iron(III) atom is displaced by 0.474 (5) Å from the 24-atom mean plane of the porphyrin core. An Fe–Cl bond length of 2.301 (2) Å and a mean Fe–N(por) distance of 2.108 (±0.015) Å were observed in the related anionic [(TpivPP)FeCl]– compound (Schappacher et al. 1983). Similarly, Dhifet and coworkers (Dhifet et al., 2011) determined an Fe–N(por) distance of 2.065 (2) Å, an Fe–Cl distance of 2.207 (2) and an iron displacement of 0.420 (4) Å from the 24 atom mean plane of the porphyrin macrocycle.

Related literature top

For the synthesis of (TpivPP)FeCl [piv = (please define)], see: Collman et al. (1975). For the crystal structures of other neutral and anionic (TpivPP)FeCl complexes, see: Dhifet et al. (2011); Schappacher et al. (1983). For related synthetic applications of the title compound, see: Cheng et al. (2000); Nasri et al. (1997); Bominaar et al. (1992); Gismelseed et al. (1990).

Experimental top

The (TpivPP)FeCl complex with the chloride ion coordinated to iron at the protected side of the porphyrin was obtained serendipitously as follows: To a Schlenk tube equipped with a magnetic stirrer was added (TpivPP)FeCl (Collman et al., 1975) (50 mg, 0.045 mmol) and toluene (10 mL). p-Fluorophenylmagnesium bromide in THF (0.05 mL, 0.05 mmol) was then added drop-wise and the mixture stirred under N2 in the dark for 24 h. The resulting red solution was filtered into a clean Schlenk tube and the toluene solution reduced to ca 3 mL under vacuum. Hexane (10 mL) was added to the solution and placed in a -20 °C freezer overnight. The solid obtained was collected by filtration and dried in vacuo to give a black microcrystalline product. The IR (KBr) spectrum of the product shows a strong νCO band at 1694 cm-1. X-ray quality crystals were obtained from slow evaporation of dichloromethane/ hexane solution of the complex at room temperature under N2. We are unsure if the title complex with the chloride in the protected porphyrin cavity was present as a component of our bulk starting reagent (TpivPP)FeCl.

Refinement top

H atoms were located geometrically and refined using a riding model on their parent atoms, with C—H = 0.95 Å for aromatic and 0.98 Å for aliphatic, with Uiso(H) = 1.2–1.5Ueq(C). The selected crystal was twinned by a 2-fold rotation about the (0 0 1) axis with a refined twin ratio of 0.4086 (16). The methyl groups of three of the t-butyl substituents were disordered: the occupancies of atoms C29 – C31 were refined to 0.759 (13) and 0.241 (13) for the unprimed and primed atoms; the occupancies of atoms C40 – C42 refined to 0.894 (9) and 0.106 (9) for the unprimed and primed atoms; and the occupancies for atoms C62 – C64 refined to 0.807 (9) and 0.192 (9) for the unprimed and primed atoms. The 1–2 and 1–3 distances of the carbons of the disordered methyl groups were set to approximately equal. The displacement parameters of the disordered carbons were restrained to be approximately equal along bonds. Two reflections, i.e. (-4 1 1) and (-5 6 4), were omitted from the final refinement owing to poor agreement. A single large (1.25 e Å3) peak was observed in the difference map about half way between the Fe and Cl

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound (I), showing the atom-labelling scheme and displacement ellipsoids drawn at the 50% probability level. Disordered groups and H atoms have been omitted for clarity.
[Figure 2] Fig. 2. The packing arrangement of molecules of the title compound (I).
Chlorido{5,10,15,20-tetrakis[2-(2,2-dimethylpropanamido)phenyl]porphyrinato-κ4N}iron(III) top
Crystal data top
[Fe(C64H64N8O4)Cl]F(000) = 2316
Mr = 1100.53Dx = 1.236 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 17.763 (3) ÅCell parameters from 5492 reflections
b = 17.652 (3) Åθ = 2.2–23.8°
c = 20.145 (4) ŵ = 0.35 mm−1
β = 110.570 (4)°T = 100 K
V = 5913.8 (18) Å3Plate, black
Z = 40.41 × 0.24 × 0.11 mm
Data collection top
Bruker APEX CCD
diffractometer		9442 reflections with I > 2σ(I)
ϕ and ω scansRint = 0.077
Absorption correction: multi-scan
(SADABS; Bruker, 2002)		θmax = 26.0°, θmin = 1.7°
Tmin = 0.869, Tmax = 0.962h = −21→19
69995 measured reflectionsk = 0→21
18970 independent reflectionsl = 0→24
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.092Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.280H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.150P)2]
where P = (Fo2 + 2Fc2)/3
18970 reflections(Δ/σ)max = 0.005
788 parametersΔρmax = 1.25 e Å−3
279 restraintsΔρmin = −0.45 e Å−3
Crystal data top
[Fe(C64H64N8O4)Cl]V = 5913.8 (18) Å3
Mr = 1100.53Z = 4
Monoclinic, P21/nMo Kα radiation
a = 17.763 (3) ŵ = 0.35 mm−1
b = 17.652 (3) ÅT = 100 K
c = 20.145 (4) Å0.41 × 0.24 × 0.11 mm
β = 110.570 (4)°
Data collection top
Bruker APEX CCD
diffractometer		18970 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2002)		9442 reflections with I > 2σ(I)
Tmin = 0.869, Tmax = 0.962Rint = 0.077
69995 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.092279 restraints
wR(F2) = 0.280H-atom parameters constrained
S = 1.01Δρmax = 1.25 e Å−3
18970 reflectionsΔρmin = −0.45 e Å−3
788 parameters
Special details top

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. Refined as a 2-component twin. Twinned about (0 0 1) with twin ratio of

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Fe10.28128 (5)0.24482 (5)0.58789 (6)0.0518 (3)
Cl10.24722 (12)0.24555 (12)0.47072 (11)0.0795 (6)
O10.5890 (4)0.3629 (3)0.4317 (4)0.101 (2)
O20.3379 (3)−0.1138 (3)0.4215 (3)0.0749 (17)
O3−0.1459 (3)0.1483 (3)0.3801 (3)0.0772 (17)
O40.1158 (3)0.6157 (3)0.4189 (3)0.0829 (17)
N10.3581 (3)0.3363 (3)0.6157 (3)0.0481 (15)
N20.3815 (3)0.1779 (3)0.6188 (3)0.0492 (15)
N30.2198 (3)0.1531 (3)0.6065 (3)0.0459 (15)
N40.1959 (3)0.3119 (3)0.6070 (3)0.0461 (14)
N50.5293 (4)0.3116 (4)0.5038 (5)0.080 (2)
H5N0.48330.29260.50320.096*
N60.3134 (3)−0.0315 (3)0.4977 (4)0.0672 (19)
H6N0.29700.01530.49960.081*
N7−0.0328 (3)0.1885 (3)0.4671 (4)0.0624 (17)
H7N0.01680.20310.47450.075*
N80.1891 (4)0.5272 (3)0.4954 (4)0.0695 (19)
H8N0.20900.48140.49680.083*
C10.3360 (4)0.4114 (3)0.6154 (4)0.0470 (18)
C20.4011 (4)0.4596 (4)0.6177 (4)0.063 (2)
H20.40040.51350.61740.076*
C30.4639 (4)0.4154 (3)0.6202 (4)0.065 (2)
H30.51590.43170.62290.078*
C40.4360 (4)0.3372 (3)0.6180 (4)0.059 (2)
C50.4847 (4)0.2743 (3)0.6208 (4)0.054 (2)
C60.4583 (4)0.1992 (3)0.6222 (4)0.0494 (18)
C70.5074 (4)0.1332 (3)0.6258 (4)0.060 (2)
H70.56150.13270.62730.072*
C80.4617 (4)0.0720 (4)0.6265 (4)0.058 (2)
H80.47810.02050.62960.070*
C90.3844 (4)0.0992 (3)0.6216 (4)0.0451 (17)
C100.3208 (4)0.0526 (3)0.6185 (4)0.0504 (19)
C110.2430 (4)0.0783 (3)0.6108 (4)0.0466 (18)
C120.1769 (4)0.0300 (4)0.6064 (4)0.057 (2)
H120.1773−0.02380.60710.068*
C130.1142 (4)0.0750 (3)0.6010 (4)0.056 (2)
H130.06230.05830.59830.067*
C140.1383 (4)0.1522 (4)0.6002 (4)0.0510 (19)
C150.0918 (4)0.2151 (4)0.5979 (4)0.0476 (18)
C160.1186 (4)0.2891 (3)0.6015 (4)0.0500 (19)
C170.0720 (4)0.3562 (4)0.6020 (4)0.065 (2)
H170.01720.35690.59820.078*
C180.1189 (4)0.4168 (4)0.6086 (4)0.064 (2)
H180.10400.46810.61120.077*
C190.1968 (4)0.3895 (3)0.6112 (4)0.0523 (19)
C200.2623 (4)0.4376 (3)0.6168 (4)0.0529 (19)
C210.5717 (4)0.2871 (4)0.6281 (5)0.063 (2)
C220.6307 (5)0.2797 (4)0.6937 (5)0.076 (3)
H220.61670.26450.73310.091*
C230.7124 (5)0.2945 (4)0.7030 (6)0.084 (3)
H230.75380.29020.74810.100*
C240.7288 (5)0.3154 (4)0.6437 (6)0.085 (3)
H240.78310.32600.64910.102*
C250.6720 (5)0.3218 (4)0.5778 (6)0.078 (3)
H250.68670.33610.53860.093*
C260.5915 (5)0.3069 (4)0.5689 (6)0.069 (2)
C270.5277 (6)0.3408 (4)0.4410 (6)0.094 (3)
C280.4473 (6)0.3423 (4)0.3827 (5)0.107 (3)
C290.4548 (7)0.3817 (7)0.3172 (5)0.108 (4)0.759 (13)
H29A0.40210.38270.27910.162*0.759 (13)
H29B0.47390.43380.32960.162*0.759 (13)
H29C0.49310.35400.30130.162*0.759 (13)
C300.3895 (6)0.3901 (8)0.4075 (6)0.126 (4)0.759 (13)
H30A0.33650.39170.36990.189*0.759 (13)
H30B0.38470.36730.45020.189*0.759 (13)
H30C0.41060.44180.41830.189*0.759 (13)
C310.4144 (7)0.2624 (5)0.3636 (7)0.135 (4)0.759 (13)
H31A0.36190.26480.32530.203*0.759 (13)
H31B0.45170.23270.34780.203*0.759 (13)
H31C0.40850.23820.40530.203*0.759 (13)
C29'0.4340 (13)0.4169 (10)0.3415 (14)0.119 (5)0.241 (13)
H29D0.38110.41620.30370.179*0.241 (13)
H29E0.43670.45920.37370.179*0.241 (13)
H29F0.47580.42300.32050.179*0.241 (13)
C30'0.3798 (7)0.330 (2)0.4128 (10)0.125 (4)0.241 (13)
H30D0.32760.33160.37400.187*0.241 (13)
H30E0.38690.28140.43690.187*0.241 (13)
H30F0.38180.37100.44670.187*0.241 (13)
C31'0.4430 (13)0.2764 (14)0.3310 (12)0.118 (5)0.241 (13)
H31D0.39050.27690.29260.177*0.241 (13)
H31E0.48560.28230.31110.177*0.241 (13)
H31F0.45000.22820.35660.177*0.241 (13)
C320.3354 (4)−0.0323 (4)0.6227 (4)0.0540 (19)
C330.3485 (4)−0.0700 (4)0.6847 (5)0.067 (2)
H330.3467−0.04330.72510.080*
C340.3646 (4)−0.1474 (4)0.6894 (5)0.074 (2)
H340.3747−0.17320.73300.089*
C350.3660 (4)−0.1858 (4)0.6316 (5)0.071 (3)
H350.3779−0.23850.63540.085*
C360.3503 (4)−0.1501 (4)0.5671 (5)0.065 (2)
H360.3509−0.17780.52680.078*
C370.3334 (4)−0.0706 (4)0.5620 (5)0.059 (2)
C380.3143 (4)−0.0517 (4)0.4325 (5)0.062 (2)
C390.2854 (3)0.0083 (4)0.3748 (4)0.083 (2)
C400.3472 (5)0.0736 (4)0.3936 (5)0.094 (3)0.894 (9)
H40A0.32970.11290.35700.140*0.894 (9)
H40B0.35140.09520.43960.140*0.894 (9)
H40C0.39980.05410.39620.140*0.894 (9)
C410.2019 (5)0.0379 (5)0.3702 (5)0.094 (3)0.894 (9)
H41A0.18370.07650.33300.141*0.894 (9)
H41B0.1635−0.00420.35890.141*0.894 (9)
H41C0.20550.06010.41580.141*0.894 (9)
C420.2797 (6)−0.0275 (5)0.3032 (4)0.113 (3)0.894 (9)
H42A0.26110.01070.26560.170*0.894 (9)
H42B0.3328−0.04610.30620.170*0.894 (9)
H42C0.2415−0.06980.29230.170*0.894 (9)
C40'0.3565 (12)0.033 (2)0.352 (2)0.095 (4)0.106 (9)
H40D0.33820.07120.31500.143*0.106 (9)
H40E0.39960.05340.39310.143*0.106 (9)
H40F0.3765−0.01160.33390.143*0.106 (9)
C41'0.254 (3)0.0775 (14)0.4042 (13)0.090 (5)0.106 (9)
H41D0.23530.11630.36720.135*0.106 (9)
H41E0.20920.06180.41890.135*0.106 (9)
H41F0.29730.09820.44500.135*0.106 (9)
C42'0.217 (2)−0.0251 (14)0.3105 (13)0.103 (5)0.106 (9)
H42D0.19860.01340.27320.154*0.106 (9)
H42E0.2377−0.06910.29230.154*0.106 (9)
H42F0.1726−0.04080.32520.154*0.106 (9)
C430.0049 (4)0.2034 (4)0.5921 (5)0.059 (2)
C44−0.0138 (4)0.2080 (5)0.6522 (5)0.077 (3)
H440.02670.21930.69650.093*
C45−0.0948 (5)0.1956 (5)0.6477 (6)0.094 (3)
H45−0.10870.19700.68910.113*
C46−0.1506 (5)0.1820 (4)0.5847 (6)0.078 (3)
H46−0.20450.17460.58200.094*
C47−0.1336 (4)0.1781 (3)0.5224 (5)0.063 (2)
H47−0.17490.16820.47820.075*
C48−0.0542 (4)0.1890 (3)0.5265 (4)0.0477 (18)
C49−0.0750 (5)0.1693 (4)0.4000 (5)0.065 (2)
C50−0.0348 (5)0.1766 (4)0.3439 (5)0.070 (2)
C510.0565 (5)0.1964 (6)0.3764 (5)0.112 (4)
H51A0.08470.15660.40990.168*
H51B0.07890.19990.33850.168*
H51C0.06320.24500.40140.168*
C52−0.0396 (6)0.1008 (5)0.3067 (5)0.114 (4)
H52A−0.01230.06200.34170.171*
H52B−0.09610.08660.28320.171*
H52C−0.01350.10490.27140.171*
C53−0.0760 (6)0.2391 (5)0.2927 (5)0.104 (3)
H53A−0.07160.28680.31870.155*
H53B−0.05030.24460.25710.155*
H53C−0.13290.22630.26900.155*
C540.2511 (4)0.5210 (4)0.6223 (5)0.0521 (19)
C550.2753 (4)0.5551 (4)0.6882 (5)0.071 (2)
H550.29980.52530.72940.085*
C560.2645 (4)0.6327 (4)0.6953 (5)0.073 (2)
H560.28130.65610.74070.088*
C570.2291 (4)0.6736 (4)0.6352 (6)0.073 (3)
H570.22230.72650.63970.088*
C580.2028 (4)0.6427 (4)0.5688 (5)0.064 (2)
H580.17720.67330.52840.077*
C590.2144 (4)0.5641 (4)0.5614 (5)0.059 (2)
C600.1412 (4)0.5483 (4)0.4319 (5)0.070 (2)
C610.1164 (4)0.4912 (4)0.3733 (5)0.085 (2)
C620.0623 (6)0.4316 (5)0.3889 (6)0.110 (3)0.807 (9)
H62A0.04600.39420.35050.166*0.807 (9)
H62B0.09180.40630.43380.166*0.807 (9)
H62C0.01440.45630.39230.166*0.807 (9)
C630.0711 (7)0.5290 (5)0.3027 (4)0.107 (3)0.807 (9)
H63A0.05540.49070.26510.160*0.807 (9)
H63B0.02280.55380.30530.160*0.807 (9)
H63C0.10570.56690.29230.160*0.807 (9)
C640.1900 (5)0.4507 (5)0.3677 (5)0.092 (3)0.807 (9)
H64A0.17270.41360.32920.138*0.807 (9)
H64B0.22580.48780.35800.138*0.807 (9)
H64C0.21870.42470.41250.138*0.807 (9)
C62'0.0261 (6)0.4756 (18)0.3494 (15)0.104 (4)0.193 (9)
H62D0.01110.43820.31110.155*0.193 (9)
H62E0.01290.45600.38950.155*0.193 (9)
H62F−0.00360.52280.33240.155*0.193 (9)
C63'0.134 (2)0.5210 (12)0.3090 (9)0.101 (4)0.193 (9)
H63D0.11770.48310.27100.151*0.193 (9)
H63E0.10430.56800.29230.151*0.193 (9)
H63F0.19190.53080.32250.151*0.193 (9)
C64'0.1605 (18)0.4161 (8)0.3960 (10)0.099 (5)0.193 (9)
H64D0.14290.38020.35630.149*0.193 (9)
H64E0.21860.42450.40980.149*0.193 (9)
H64F0.14850.39540.43630.149*0.193 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.0358 (6)0.0378 (5)0.0886 (8)0.0041 (4)0.0304 (6)0.0061 (6)
Cl10.0761 (15)0.0817 (14)0.0813 (15)−0.0009 (11)0.0281 (12)0.0111 (13)
O10.083 (4)0.071 (4)0.176 (7)0.002 (3)0.077 (5)0.028 (4)
O20.070 (3)0.048 (3)0.136 (5)0.005 (3)0.072 (4)−0.006 (3)
O30.047 (3)0.047 (3)0.127 (5)−0.008 (2)0.017 (3)0.005 (3)
O40.062 (4)0.060 (3)0.132 (5)0.012 (3)0.042 (4)0.021 (3)
N10.036 (3)0.032 (3)0.086 (5)0.004 (2)0.034 (3)0.004 (3)
N20.033 (3)0.032 (3)0.084 (5)0.002 (2)0.023 (3)−0.002 (3)
N30.031 (3)0.028 (3)0.081 (4)0.003 (2)0.023 (3)0.009 (3)
N40.034 (3)0.034 (3)0.079 (4)0.003 (2)0.031 (3)0.006 (3)
N50.060 (5)0.076 (5)0.131 (7)−0.007 (4)0.067 (5)0.007 (5)
N60.062 (4)0.035 (3)0.104 (6)0.010 (3)0.028 (4)−0.005 (4)
N70.036 (4)0.061 (4)0.088 (5)−0.013 (3)0.018 (4)0.005 (4)
N80.069 (5)0.048 (4)0.090 (6)0.027 (3)0.027 (4)0.021 (4)
C10.037 (4)0.030 (3)0.085 (6)0.009 (3)0.035 (4)0.007 (3)
C20.044 (4)0.033 (4)0.126 (7)0.007 (3)0.045 (5)0.005 (4)
C30.046 (4)0.039 (4)0.125 (7)−0.007 (3)0.050 (5)−0.004 (4)
C40.041 (4)0.033 (4)0.115 (7)0.003 (3)0.041 (4)0.000 (4)
C50.041 (4)0.034 (3)0.096 (6)0.005 (3)0.035 (4)−0.002 (4)
C60.035 (4)0.038 (4)0.080 (6)0.006 (3)0.026 (4)−0.005 (4)
C70.036 (4)0.035 (4)0.111 (7)0.004 (3)0.028 (4)−0.009 (4)
C80.043 (4)0.030 (4)0.098 (6)0.001 (3)0.021 (4)−0.009 (4)
C90.027 (3)0.033 (3)0.074 (5)−0.002 (3)0.016 (3)−0.003 (3)
C100.033 (4)0.037 (4)0.077 (5)0.008 (3)0.015 (4)−0.002 (4)
C110.034 (4)0.033 (3)0.076 (5)−0.003 (3)0.023 (4)0.006 (3)
C120.040 (4)0.038 (4)0.098 (6)0.002 (3)0.030 (4)0.008 (4)
C130.030 (4)0.041 (4)0.101 (6)−0.004 (3)0.029 (4)0.015 (4)
C140.035 (4)0.043 (4)0.079 (6)−0.002 (3)0.025 (4)0.009 (4)
C150.030 (4)0.046 (4)0.071 (5)0.001 (3)0.023 (4)0.010 (3)
C160.030 (4)0.040 (4)0.085 (6)0.015 (3)0.026 (4)0.017 (4)
C170.041 (4)0.048 (4)0.119 (7)0.008 (3)0.044 (5)0.008 (4)
C180.051 (5)0.042 (4)0.117 (7)0.011 (3)0.053 (5)0.012 (4)
C190.032 (4)0.040 (4)0.092 (6)0.008 (3)0.032 (4)0.013 (4)
C200.044 (4)0.035 (4)0.085 (6)0.006 (3)0.030 (4)0.010 (4)
C210.044 (5)0.033 (4)0.117 (8)0.009 (3)0.034 (5)−0.015 (4)
C220.051 (5)0.053 (4)0.125 (8)0.007 (4)0.034 (6)−0.015 (5)
C230.052 (5)0.062 (5)0.151 (10)−0.013 (4)0.054 (6)−0.032 (6)
C240.044 (5)0.053 (5)0.169 (11)0.001 (4)0.050 (7)−0.022 (6)
C250.043 (5)0.062 (5)0.147 (9)−0.004 (4)0.057 (6)−0.006 (5)
C260.047 (5)0.044 (4)0.131 (9)0.004 (4)0.049 (6)−0.010 (5)
C270.088 (8)0.064 (5)0.164 (11)0.018 (5)0.085 (8)0.022 (6)
C280.082 (7)0.102 (6)0.145 (9)0.012 (5)0.051 (7)0.027 (5)
C290.112 (8)0.086 (7)0.140 (8)−0.003 (6)0.060 (6)0.006 (6)
C300.097 (7)0.140 (8)0.159 (9)0.028 (6)0.068 (6)0.048 (7)
C310.107 (8)0.113 (6)0.171 (10)−0.022 (6)0.029 (7)0.033 (6)
C29'0.111 (9)0.109 (7)0.151 (10)0.013 (8)0.063 (8)0.032 (7)
C30'0.092 (9)0.129 (10)0.164 (10)0.009 (8)0.058 (7)0.045 (8)
C31'0.103 (9)0.103 (8)0.151 (10)−0.015 (8)0.048 (8)0.019 (7)
C320.032 (4)0.043 (4)0.083 (6)−0.004 (3)0.016 (4)−0.004 (4)
C330.048 (5)0.051 (4)0.092 (7)0.003 (3)0.014 (4)0.008 (4)
C340.063 (5)0.044 (4)0.110 (8)0.008 (4)0.023 (5)0.011 (5)
C350.050 (5)0.031 (4)0.129 (8)0.005 (3)0.027 (5)0.003 (5)
C360.029 (4)0.036 (4)0.123 (8)0.003 (3)0.018 (4)−0.012 (4)
C370.029 (4)0.041 (4)0.103 (7)0.004 (3)0.018 (4)−0.003 (5)
C380.040 (4)0.060 (5)0.098 (7)−0.001 (4)0.038 (5)−0.012 (5)
C390.078 (5)0.080 (5)0.105 (6)0.024 (4)0.048 (5)0.005 (5)
C400.088 (6)0.092 (6)0.113 (7)0.012 (4)0.051 (5)0.028 (5)
C410.072 (5)0.097 (6)0.112 (7)0.034 (5)0.031 (5)0.010 (5)
C420.111 (7)0.125 (7)0.102 (6)0.051 (6)0.034 (5)−0.002 (5)
C40'0.092 (8)0.107 (9)0.104 (9)0.028 (7)0.056 (7)0.016 (8)
C41'0.080 (8)0.089 (8)0.111 (9)0.032 (7)0.047 (7)0.011 (7)
C42'0.088 (8)0.112 (9)0.106 (9)0.034 (8)0.032 (8)0.003 (7)
C430.051 (5)0.039 (4)0.098 (7)0.016 (3)0.040 (5)0.023 (4)
C440.042 (5)0.099 (7)0.092 (7)−0.007 (4)0.025 (5)0.020 (5)
C450.054 (6)0.133 (8)0.111 (9)0.003 (6)0.049 (6)0.032 (7)
C460.041 (5)0.073 (6)0.126 (9)−0.006 (4)0.035 (6)0.024 (6)
C470.039 (4)0.043 (4)0.109 (7)0.002 (3)0.029 (5)0.014 (4)
C480.036 (4)0.039 (4)0.073 (6)0.000 (3)0.024 (4)0.010 (4)
C490.051 (5)0.036 (4)0.108 (8)−0.003 (4)0.029 (5)0.003 (4)
C500.057 (5)0.052 (5)0.097 (7)−0.008 (4)0.021 (5)−0.013 (5)
C510.075 (7)0.148 (10)0.135 (9)−0.003 (6)0.064 (7)−0.003 (7)
C520.137 (9)0.073 (6)0.152 (10)0.000 (6)0.077 (8)−0.022 (6)
C530.108 (8)0.081 (6)0.131 (9)0.012 (6)0.052 (7)0.018 (6)
C540.039 (4)0.036 (4)0.092 (6)0.008 (3)0.036 (4)0.007 (4)
C550.056 (5)0.051 (5)0.109 (8)0.015 (4)0.033 (5)0.005 (5)
C560.063 (5)0.045 (4)0.115 (7)0.021 (4)0.035 (5)0.012 (5)
C570.050 (5)0.044 (4)0.135 (9)0.004 (4)0.043 (6)−0.010 (5)
C580.050 (5)0.034 (4)0.117 (8)0.011 (3)0.041 (5)0.013 (4)
C590.045 (4)0.039 (4)0.102 (7)0.002 (3)0.037 (5)0.007 (5)
C600.054 (5)0.052 (5)0.122 (8)0.001 (4)0.053 (6)0.005 (5)
C610.066 (5)0.080 (5)0.115 (6)0.015 (4)0.040 (5)0.011 (5)
C620.087 (6)0.092 (7)0.149 (8)−0.017 (5)0.037 (6)−0.004 (6)
C630.099 (7)0.089 (6)0.122 (7)0.034 (5)0.024 (6)0.006 (5)
C640.105 (6)0.095 (7)0.093 (7)0.044 (5)0.057 (5)0.016 (5)
C62'0.078 (6)0.089 (9)0.138 (10)0.004 (7)0.029 (7)0.003 (8)
C63'0.102 (9)0.098 (9)0.109 (8)0.028 (8)0.045 (7)0.013 (7)
C64'0.097 (8)0.087 (8)0.119 (9)0.026 (7)0.046 (9)0.009 (7)
Geometric parameters (Å, º) top
Fe1—N22.043 (5)C31'—H31F0.9800
Fe1—N12.060 (5)C32—C331.361 (10)
Fe1—N32.060 (5)C32—C371.387 (10)
Fe1—N42.063 (5)C33—C341.393 (9)
Fe1—Cl12.221 (2)C33—H330.9500
O1—C271.231 (9)C34—C351.355 (11)
O2—C381.221 (7)C34—H340.9500
O3—C491.237 (8)C35—C361.382 (11)
O4—C601.267 (8)C35—H350.9500
N1—C41.370 (7)C36—C371.431 (9)
N1—C11.382 (7)C36—H360.9500
N2—C91.391 (7)C38—C391.522 (11)
N2—C61.392 (7)C39—C401.544 (6)
N3—C111.377 (7)C39—C41'1.545 (7)
N3—C141.407 (7)C39—C42'1.545 (7)
N4—C191.372 (7)C39—C411.545 (6)
N4—C161.398 (7)C39—C40'1.545 (7)
N5—C271.358 (10)C39—C421.546 (6)
N5—C261.389 (11)C40—H40A0.9800
N5—H5N0.8800C40—H40B0.9800
N6—C381.366 (9)C40—H40C0.9800
N6—C371.399 (9)C41—H41A0.9800
N6—H6N0.8800C41—H41B0.9800
N7—C491.339 (9)C41—H41C0.9800
N7—C481.377 (9)C42—H42A0.9800
N7—H7N0.8800C42—H42B0.9800
N8—C601.317 (9)C42—H42C0.9800
N8—C591.404 (9)C40'—H40D0.9800
N8—H8N0.8800C40'—H40E0.9800
C1—C201.397 (8)C40'—H40F0.9800
C1—C21.425 (8)C41'—H41D0.9800
C2—C31.348 (8)C41'—H41E0.9800
C2—H20.9500C41'—H41F0.9800
C3—C41.462 (8)C42'—H42D0.9800
C3—H30.9500C42'—H42E0.9800
C4—C51.394 (8)C42'—H42F0.9800
C5—C61.410 (8)C43—C441.366 (10)
C5—C211.518 (9)C43—C481.391 (10)
C6—C71.442 (8)C44—C451.427 (10)
C7—C81.354 (8)C44—H440.9500
C7—H70.9500C45—C461.329 (11)
C8—C91.425 (8)C45—H450.9500
C8—H80.9500C46—C471.391 (11)
C9—C101.380 (8)C46—H460.9500
C10—C111.410 (8)C47—C481.395 (9)
C10—C321.518 (9)C47—H470.9500
C11—C121.428 (8)C49—C501.539 (11)
C12—C131.341 (8)C50—C531.512 (10)
C12—H120.9500C50—C521.521 (10)
C13—C141.431 (8)C50—C511.561 (10)
C13—H130.9500C51—H51A0.9800
C14—C151.375 (8)C51—H51B0.9800
C15—C161.384 (8)C51—H51C0.9800
C15—C431.521 (9)C52—H52A0.9800
C16—C171.447 (8)C52—H52B0.9800
C17—C181.334 (9)C52—H52C0.9800
C17—H170.9500C53—H53A0.9800
C18—C191.448 (8)C53—H53B0.9800
C18—H180.9500C53—H53C0.9800
C19—C201.413 (8)C54—C551.381 (10)
C20—C541.494 (8)C54—C591.397 (10)
C21—C221.374 (11)C55—C561.397 (9)
C21—C261.400 (11)C55—H550.9500
C22—C231.422 (10)C56—C571.359 (11)
C22—H220.9500C56—H560.9500
C23—C241.376 (12)C57—C581.366 (11)
C23—H230.9500C57—H570.9500
C24—C251.360 (12)C58—C591.419 (9)
C24—H240.9500C58—H580.9500
C25—C261.403 (9)C60—C611.497 (11)
C25—H250.9500C61—C631.520 (7)
C27—C281.498 (13)C61—C64'1.525 (7)
C28—C311.524 (7)C61—C641.528 (7)
C28—C29'1.529 (8)C61—C62'1.529 (7)
C28—C30'1.537 (8)C61—C621.529 (7)
C28—C291.537 (7)C61—C63'1.530 (7)
C28—C301.543 (7)C62—H62A0.9800
C28—C31'1.544 (8)C62—H62B0.9800
C29—H29A0.9800C62—H62C0.9800
C29—H29B0.9800C63—H63A0.9800
C29—H29C0.9800C63—H63B0.9800
C30—H30A0.9800C63—H63C0.9800
C30—H30B0.9800C64—H64A0.9800
C30—H30C0.9800C64—H64B0.9800
C31—H31A0.9800C64—H64C0.9800
C31—H31B0.9800C62'—H62D0.9800
C31—H31C0.9800C62'—H62E0.9800
C29'—H29D0.9800C62'—H62F0.9800
C29'—H29E0.9800C63'—H63D0.9800
C29'—H29F0.9800C63'—H63E0.9800
C30'—H30D0.9800C63'—H63F0.9800
C30'—H30E0.9800C64'—H64D0.9800
C30'—H30F0.9800C64'—H64E0.9800
C31'—H31D0.9800C64'—H64F0.9800
C31'—H31E0.9800
N2—Fe1—N187.0 (2)C34—C35—H35119.3
N2—Fe1—N387.23 (19)C36—C35—H35119.3
N1—Fe1—N3155.4 (2)C35—C36—C37118.9 (8)
N2—Fe1—N4153.4 (2)C35—C36—H36120.6
N1—Fe1—N487.7 (2)C37—C36—H36120.6
N3—Fe1—N486.90 (19)C32—C37—N6119.7 (6)
N2—Fe1—Cl1102.12 (17)C32—C37—C36118.4 (8)
N1—Fe1—Cl1101.06 (17)N6—C37—C36121.9 (8)
N3—Fe1—Cl1103.51 (17)O2—C38—N6121.9 (8)
N4—Fe1—Cl1104.53 (17)O2—C38—C39122.1 (7)
C4—N1—C1105.8 (5)N6—C38—C39116.0 (6)
C4—N1—Fe1125.7 (4)C38—C39—C40108.2 (5)
C1—N1—Fe1126.2 (4)C38—C39—C41'109.2 (6)
C9—N2—C6104.3 (5)C38—C39—C42'109.2 (7)
C9—N2—Fe1127.2 (4)C41'—C39—C42'109.9 (6)
C6—N2—Fe1126.4 (4)C38—C39—C41109.9 (5)
C11—N3—C14105.7 (5)C40—C39—C41110.3 (5)
C11—N3—Fe1126.8 (4)C38—C39—C40'109.1 (6)
C14—N3—Fe1125.9 (4)C41'—C39—C40'109.7 (6)
C19—N4—C16106.3 (5)C42'—C39—C40'109.7 (6)
C19—N4—Fe1126.3 (4)C38—C39—C42108.8 (5)
C16—N4—Fe1125.8 (4)C40—C39—C42110.0 (5)
C27—N5—C26130.7 (8)C41—C39—C42109.6 (5)
C27—N5—H5N114.7C39—C40—H40A109.5
C26—N5—H5N114.7C39—C40—H40B109.5
C38—N6—C37132.6 (6)H40A—C40—H40B109.5
C38—N6—H6N113.7C39—C40—H40C109.5
C37—N6—H6N113.7H40A—C40—H40C109.5
C49—N7—C48130.7 (6)H40B—C40—H40C109.5
C49—N7—H7N114.6C39—C41—H41A109.5
C48—N7—H7N114.6C39—C41—H41B109.5
C60—N8—C59132.2 (7)H41A—C41—H41B109.5
C60—N8—H8N113.9C39—C41—H41C109.5
C59—N8—H8N113.9H41A—C41—H41C109.5
N1—C1—C20125.8 (5)H41B—C41—H41C109.5
N1—C1—C2110.3 (5)C39—C42—H42A109.5
C20—C1—C2123.9 (5)C39—C42—H42B109.5
C3—C2—C1107.9 (6)H42A—C42—H42B109.5
C3—C2—H2126.1C39—C42—H42C109.5
C1—C2—H2126.1H42A—C42—H42C109.5
C2—C3—C4106.2 (6)H42B—C42—H42C109.5
C2—C3—H3126.9C39—C40'—H40D109.5
C4—C3—H3126.9C39—C40'—H40E109.5
N1—C4—C5126.6 (6)H40D—C40'—H40E109.5
N1—C4—C3109.8 (5)C39—C40'—H40F109.5
C5—C4—C3123.5 (6)H40D—C40'—H40F109.5
C4—C5—C6122.9 (6)H40E—C40'—H40F109.5
C4—C5—C21118.8 (6)C39—C41'—H41D109.5
C6—C5—C21118.1 (5)C39—C41'—H41E109.5
N2—C6—C5125.4 (5)H41D—C41'—H41E109.5
N2—C6—C7110.4 (5)C39—C41'—H41F109.5
C5—C6—C7124.2 (6)H41D—C41'—H41F109.5
C8—C7—C6106.9 (6)H41E—C41'—H41F109.5
C8—C7—H7126.6C39—C42'—H42D109.5
C6—C7—H7126.6C39—C42'—H42E109.5
C7—C8—C9107.3 (6)H42D—C42'—H42E109.5
C7—C8—H8126.3C39—C42'—H42F109.5
C9—C8—H8126.3H42D—C42'—H42F109.5
C10—C9—N2125.2 (5)H42E—C42'—H42F109.5
C10—C9—C8123.8 (6)C44—C43—C48121.0 (7)
N2—C9—C8111.0 (5)C44—C43—C15118.7 (8)
C9—C10—C11124.6 (6)C48—C43—C15120.3 (7)
C9—C10—C32117.7 (5)C43—C44—C45119.2 (8)
C11—C10—C32117.7 (5)C43—C44—H44120.4
N3—C11—C10125.1 (5)C45—C44—H44120.4
N3—C11—C12110.3 (5)C46—C45—C44119.0 (9)
C10—C11—C12124.6 (6)C46—C45—H45120.5
C13—C12—C11107.0 (6)C44—C45—H45120.5
C13—C12—H12126.5C45—C46—C47123.0 (8)
C11—C12—H12126.5C45—C46—H46118.5
C12—C13—C14108.7 (6)C47—C46—H46118.5
C12—C13—H13125.6C46—C47—C48118.3 (8)
C14—C13—H13125.6C46—C47—H47120.8
C15—C14—N3125.5 (6)C48—C47—H47120.8
C15—C14—C13126.2 (6)N7—C48—C43118.6 (6)
N3—C14—C13108.2 (5)N7—C48—C47121.9 (7)
C14—C15—C16124.6 (6)C43—C48—C47119.4 (7)
C14—C15—C43118.3 (6)O3—C49—N7123.2 (8)
C16—C15—C43117.0 (5)O3—C49—C50118.0 (8)
C15—C16—N4126.0 (5)N7—C49—C50118.8 (7)
C15—C16—C17125.8 (6)C53—C50—C52112.1 (8)
N4—C16—C17108.2 (5)C53—C50—C49108.9 (7)
C18—C17—C16108.6 (6)C52—C50—C49109.1 (7)
C18—C17—H17125.7C53—C50—C51107.8 (7)
C16—C17—H17125.7C52—C50—C51105.9 (7)
C17—C18—C19106.9 (6)C49—C50—C51113.0 (7)
C17—C18—H18126.5C50—C51—H51A109.5
C19—C18—H18126.5C50—C51—H51B109.5
N4—C19—C20126.5 (5)H51A—C51—H51B109.5
N4—C19—C18109.9 (5)C50—C51—H51C109.5
C20—C19—C18123.6 (6)H51A—C51—H51C109.5
C1—C20—C19123.4 (6)H51B—C51—H51C109.5
C1—C20—C54118.6 (5)C50—C52—H52A109.5
C19—C20—C54118.0 (6)C50—C52—H52B109.5
C22—C21—C26120.6 (8)H52A—C52—H52B109.5
C22—C21—C5119.1 (8)C50—C52—H52C109.5
C26—C21—C5120.4 (8)H52A—C52—H52C109.5
C21—C22—C23120.5 (9)H52B—C52—H52C109.5
C21—C22—H22119.7C50—C53—H53A109.5
C23—C22—H22119.7C50—C53—H53B109.5
C24—C23—C22116.9 (10)H53A—C53—H53B109.5
C24—C23—H23121.6C50—C53—H53C109.5
C22—C23—H23121.6H53A—C53—H53C109.5
C25—C24—C23124.0 (8)H53B—C53—H53C109.5
C25—C24—H24118.0C55—C54—C59119.9 (7)
C23—C24—H24118.0C55—C54—C20119.8 (7)
C24—C25—C26118.9 (9)C59—C54—C20120.3 (7)
C24—C25—H25120.6C54—C55—C56121.3 (8)
C26—C25—H25120.6C54—C55—H55119.4
N5—C26—C21117.7 (7)C56—C55—H55119.4
N5—C26—C25123.1 (9)C57—C56—C55117.8 (9)
C21—C26—C25119.2 (9)C57—C56—H56121.1
O1—C27—N5122.2 (10)C55—C56—H56121.1
O1—C27—C28121.7 (8)C56—C57—C58123.5 (7)
N5—C27—C28116.1 (7)C56—C57—H57118.2
C27—C28—C31111.0 (6)C58—C57—H57118.2
C27—C28—C29'111.3 (7)C57—C58—C59118.8 (8)
C27—C28—C30'110.4 (7)C57—C58—H58120.6
C29'—C28—C30'109.8 (7)C59—C58—H58120.6
C27—C28—C29109.6 (6)C54—C59—N8118.4 (6)
C31—C28—C29110.1 (6)C54—C59—C58118.7 (8)
C27—C28—C30108.3 (6)N8—C59—C58122.9 (8)
C31—C28—C30110.4 (6)O4—C60—N8121.9 (8)
C29—C28—C30107.4 (6)O4—C60—C61119.0 (7)
C27—C28—C31'108.9 (7)N8—C60—C61119.2 (6)
C29'—C28—C31'108.7 (7)C60—C61—C63110.7 (6)
C30'—C28—C31'107.6 (7)C60—C61—C64'111.8 (7)
C28—C29—H29A109.5C60—C61—C64110.5 (6)
C28—C29—H29B109.5C63—C61—C64108.9 (6)
H29A—C29—H29B109.5C60—C61—C62'110.7 (7)
C28—C29—H29C109.5C64'—C61—C62'108.1 (7)
H29A—C29—H29C109.5C60—C61—C62109.4 (6)
H29B—C29—H29C109.5C63—C61—C62109.2 (6)
C28—C30—H30A109.5C64—C61—C62108.0 (6)
C28—C30—H30B109.5C60—C61—C63'110.2 (7)
H30A—C30—H30B109.5C64'—C61—C63'108.4 (7)
C28—C30—H30C109.5C62'—C61—C63'107.5 (7)
H30A—C30—H30C109.5C61—C62—H62A109.5
H30B—C30—H30C109.5C61—C62—H62B109.5
C28—C31—H31A109.5H62A—C62—H62B109.5
C28—C31—H31B109.5C61—C62—H62C109.5
H31A—C31—H31B109.5H62A—C62—H62C109.5
C28—C31—H31C109.5H62B—C62—H62C109.5
H31A—C31—H31C109.5C61—C63—H63A109.5
H31B—C31—H31C109.5C61—C63—H63B109.5
C28—C29'—H29D109.5H63A—C63—H63B109.5
C28—C29'—H29E109.5C61—C63—H63C109.5
H29D—C29'—H29E109.5H63A—C63—H63C109.5
C28—C29'—H29F109.5H63B—C63—H63C109.5
H29D—C29'—H29F109.5C61—C64—H64A109.5
H29E—C29'—H29F109.5C61—C64—H64B109.5
C28—C30'—H30D109.5H64A—C64—H64B109.5
C28—C30'—H30E109.5C61—C64—H64C109.5
H30D—C30'—H30E109.5H64A—C64—H64C109.5
C28—C30'—H30F109.5H64B—C64—H64C109.5
H30D—C30'—H30F109.5C61—C62'—H62D109.5
H30E—C30'—H30F109.5C61—C62'—H62E109.5
C28—C31'—H31D109.5H62D—C62'—H62E109.5
C28—C31'—H31E109.5C61—C62'—H62F109.5
H31D—C31'—H31E109.5H62D—C62'—H62F109.5
C28—C31'—H31F109.5H62E—C62'—H62F109.5
H31D—C31'—H31F109.5C61—C63'—H63D109.5
H31E—C31'—H31F109.5C61—C63'—H63E109.5
C33—C32—C37120.9 (7)H63D—C63'—H63E109.5
C33—C32—C10120.3 (7)C61—C63'—H63F109.5
C37—C32—C10118.8 (7)H63D—C63'—H63F109.5
C32—C33—C34120.5 (8)H63E—C63'—H63F109.5
C32—C33—H33119.8C61—C64'—H64D109.5
C34—C33—H33119.8C61—C64'—H64E109.5
C35—C34—C33119.9 (8)H64D—C64'—H64E109.5
C35—C34—H34120.1C61—C64'—H64F109.5
C33—C34—H34120.1H64D—C64'—H64F109.5
C34—C35—C36121.4 (7)H64E—C64'—H64F109.5
C4—N1—C1—C20−176.7 (7)C26—N5—C27—O17.1 (13)
Fe1—N1—C1—C2020.1 (11)C26—N5—C27—C28−174.9 (7)
C4—N1—C1—C2−0.2 (8)O1—C27—C28—C31115.9 (9)
Fe1—N1—C1—C2−163.3 (5)N5—C27—C28—C31−62.0 (9)
N1—C1—C2—C3−0.7 (9)O1—C27—C28—C29'−44.0 (17)
C20—C1—C2—C3175.9 (8)N5—C27—C28—C29'138.0 (16)
C1—C2—C3—C41.2 (9)O1—C27—C28—C30'−166.3 (17)
C1—N1—C4—C5178.3 (8)N5—C27—C28—C30'15.8 (17)
Fe1—N1—C4—C5−18.4 (12)O1—C27—C28—C29−5.9 (9)
C1—N1—C4—C30.9 (9)N5—C27—C28—C29176.2 (8)
Fe1—N1—C4—C3164.2 (5)O1—C27—C28—C30−122.7 (9)
C2—C3—C4—N1−1.4 (9)N5—C27—C28—C3059.3 (8)
C2—C3—C4—C5−178.9 (8)O1—C27—C28—C31'75.8 (17)
N1—C4—C5—C6−0.4 (13)N5—C27—C28—C31'−102.2 (16)
C3—C4—C5—C6176.7 (7)C9—C10—C32—C33100.6 (8)
N1—C4—C5—C21−175.8 (8)C11—C10—C32—C33−80.2 (9)
C3—C4—C5—C211.3 (12)C9—C10—C32—C37−80.7 (8)
C9—N2—C6—C5179.8 (7)C11—C10—C32—C3798.5 (8)
Fe1—N2—C6—C515.5 (10)C37—C32—C33—C343.5 (11)
C9—N2—C6—C71.1 (8)C10—C32—C33—C34−177.8 (6)
Fe1—N2—C6—C7−163.2 (5)C32—C33—C34—C35−1.1 (11)
C4—C5—C6—N22.1 (13)C33—C34—C35—C36−1.0 (12)
C21—C5—C6—N2177.5 (7)C34—C35—C36—C370.7 (11)
C4—C5—C6—C7−179.4 (8)C33—C32—C37—N6174.9 (6)
C21—C5—C6—C7−4.0 (12)C10—C32—C37—N6−3.8 (9)
N2—C6—C7—C8−1.6 (9)C33—C32—C37—C36−3.8 (10)
C5—C6—C7—C8179.7 (7)C10—C32—C37—C36177.5 (5)
C6—C7—C8—C91.4 (9)C38—N6—C37—C32172.5 (7)
C6—N2—C9—C10−178.7 (7)C38—N6—C37—C36−8.9 (11)
Fe1—N2—C9—C10−14.6 (10)C35—C36—C37—C321.7 (10)
C6—N2—C9—C8−0.2 (8)C35—C36—C37—N6−177.0 (6)
Fe1—N2—C9—C8163.9 (5)C37—N6—C38—O2−2.4 (11)
C7—C8—C9—C10177.8 (7)C37—N6—C38—C39178.6 (6)
C7—C8—C9—N2−0.8 (9)O2—C38—C39—C40−111.1 (7)
N2—C9—C10—C111.0 (12)N6—C38—C39—C4068.0 (7)
C8—C9—C10—C11−177.3 (8)O2—C38—C39—C41'176 (2)
N2—C9—C10—C32−179.8 (7)N6—C38—C39—C41'−5 (2)
C8—C9—C10—C321.9 (11)O2—C38—C39—C42'56 (2)
C14—N3—C11—C10−179.3 (7)N6—C38—C39—C42'−125 (2)
Fe1—N3—C11—C1014.5 (10)O2—C38—C39—C41128.4 (7)
C14—N3—C11—C120.8 (8)N6—C38—C39—C41−52.5 (7)
Fe1—N3—C11—C12−165.5 (5)O2—C38—C39—C40'−64 (2)
C9—C10—C11—N3−1.1 (12)N6—C38—C39—C40'115 (2)
C32—C10—C11—N3179.8 (7)O2—C38—C39—C428.4 (8)
C9—C10—C11—C12178.9 (7)N6—C38—C39—C42−172.5 (6)
C32—C10—C11—C12−0.3 (11)C14—C15—C43—C4499.1 (9)
N3—C11—C12—C13−1.4 (9)C16—C15—C43—C44−80.1 (9)
C10—C11—C12—C13178.6 (8)C14—C15—C43—C48−81.6 (8)
C11—C12—C13—C141.4 (9)C16—C15—C43—C4899.2 (8)
C11—N3—C14—C15176.5 (7)C48—C43—C44—C451.9 (12)
Fe1—N3—C14—C15−17.1 (10)C15—C43—C44—C45−178.7 (7)
C11—N3—C14—C130.1 (8)C43—C44—C45—C46−1.9 (13)
Fe1—N3—C14—C13166.5 (5)C44—C45—C46—C471.0 (14)
C12—C13—C14—C15−177.4 (7)C45—C46—C47—C48−0.1 (12)
C12—C13—C14—N3−1.0 (9)C49—N7—C48—C43172.7 (7)
N3—C14—C15—C160.1 (12)C49—N7—C48—C47−9.4 (11)
C13—C14—C15—C16175.9 (7)C44—C43—C48—N7177.0 (6)
N3—C14—C15—C43−179.1 (7)C15—C43—C48—N7−2.3 (9)
C13—C14—C15—C43−3.3 (12)C44—C43—C48—C47−1.0 (10)
C14—C15—C16—N40.8 (12)C15—C43—C48—C47179.7 (5)
C43—C15—C16—N4180.0 (7)C46—C47—C48—N7−177.9 (6)
C14—C15—C16—C17−177.4 (7)C46—C47—C48—C430.1 (10)
C43—C15—C16—C171.7 (11)C48—N7—C49—O30.9 (12)
C19—N4—C16—C15−178.1 (7)C48—N7—C49—C50178.4 (6)
Fe1—N4—C16—C1515.3 (10)O3—C49—C50—C5365.4 (8)
C19—N4—C16—C170.4 (8)N7—C49—C50—C53−112.3 (8)
Fe1—N4—C16—C17−166.2 (5)O3—C49—C50—C52−57.3 (9)
C15—C16—C17—C18177.6 (8)N7—C49—C50—C52125.1 (7)
N4—C16—C17—C18−0.9 (9)O3—C49—C50—C51−174.8 (7)
C16—C17—C18—C191.0 (9)N7—C49—C50—C517.5 (10)
C16—N4—C19—C20−179.4 (7)C1—C20—C54—C55−86.1 (9)
Fe1—N4—C19—C20−12.9 (11)C19—C20—C54—C5595.7 (8)
C16—N4—C19—C180.2 (8)C1—C20—C54—C5995.4 (8)
Fe1—N4—C19—C18166.7 (5)C19—C20—C54—C59−82.8 (8)
C17—C18—C19—N4−0.8 (9)C59—C54—C55—C56−0.5 (11)
C17—C18—C19—C20178.8 (8)C20—C54—C55—C56−179.0 (6)
N1—C1—C20—C19−7.0 (12)C54—C55—C56—C570.1 (11)
C2—C1—C20—C19176.9 (7)C55—C56—C57—C580.9 (12)
N1—C1—C20—C54174.9 (7)C56—C57—C58—C59−1.6 (11)
C2—C1—C20—C54−1.2 (11)C55—C54—C59—N8−178.7 (6)
N4—C19—C20—C13.1 (12)C20—C54—C59—N8−0.2 (9)
C18—C19—C20—C1−176.4 (8)C55—C54—C59—C58−0.2 (10)
N4—C19—C20—C54−178.7 (7)C20—C54—C59—C58178.3 (6)
C18—C19—C20—C541.7 (11)C60—N8—C59—C54165.6 (7)
C4—C5—C21—C22100.0 (9)C60—N8—C59—C58−12.9 (12)
C6—C5—C21—C22−75.6 (9)C57—C58—C59—C541.1 (10)
C4—C5—C21—C26−79.3 (9)C57—C58—C59—N8179.6 (6)
C6—C5—C21—C26105.0 (8)C59—N8—C60—O49.3 (12)
C26—C21—C22—C232.1 (10)C59—N8—C60—C61−171.3 (6)
C5—C21—C22—C23−177.2 (6)O4—C60—C61—C637.3 (8)
C21—C22—C23—C24−0.7 (11)N8—C60—C61—C63−172.2 (7)
C22—C23—C24—C25−0.6 (12)O4—C60—C61—C64'172.8 (16)
C23—C24—C25—C260.4 (12)N8—C60—C61—C64'−6.6 (17)
C27—N5—C26—C21167.8 (7)O4—C60—C61—C64128.0 (7)
C27—N5—C26—C25−11.4 (13)N8—C60—C61—C64−51.4 (8)
C22—C21—C26—N5178.5 (6)O4—C60—C61—C62'−66.6 (16)
C5—C21—C26—N5−2.2 (10)N8—C60—C61—C62'113.9 (17)
C22—C21—C26—C25−2.3 (10)O4—C60—C61—C62−113.1 (7)
C5—C21—C26—C25177.0 (6)N8—C60—C61—C6267.4 (8)
C24—C25—C26—N5−179.8 (7)O4—C60—C61—C63'52.3 (16)
C24—C25—C26—C211.1 (11)N8—C60—C61—C63'−127.2 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O1i0.952.433.310 (8)154
C7—H7···O2ii0.952.353.228 (8)154
C12—H12···O3iii0.952.303.223 (8)163
C17—H17···O4iv0.952.323.251 (8)168
C25—H25···O10.952.292.884 (12)120
C36—H36···O20.952.342.932 (11)120
C47—H47···O30.952.242.847 (11)121
C58—H58···O40.952.322.909 (11)119
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y, −z+1; (iii) −x, −y, −z+1; (iv) −x, −y+1, −z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O1i0.952.433.310 (8)154
C7—H7···O2ii0.952.353.228 (8)154
C12—H12···O3iii0.952.303.223 (8)163
C17—H17···O4iv0.952.323.251 (8)168
C25—H25···O10.952.292.884 (12)120
C36—H36···O20.952.342.932 (11)120
C47—H47···O30.952.242.847 (11)121
C58—H58···O40.952.322.909 (11)119
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y, −z+1; (iii) −x, −y, −z+1; (iv) −x, −y+1, −z+1.
 

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.

References

First citationBominaar, E. L., Ding, X. Q., Gismelseed, A., Bill, E., Winkler, H., Trautwein, A. X., Nasri, H., Fischer, J. & Weiss, R. (1992). J. Am. Chem. Soc. 31, 1845–1854.  Google Scholar
 First citationBruker (2002). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationBruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationCheng, L., Khan, M. A., Richter-Addo, G. B. & Powell, D. R. (2000). Chem. Commun. pp. 2301–2302.  Google Scholar
 First citationCollman, J. P., Gagne, R. R., Reed, C. A., Halbert, T. R., Lang, G. & Robinson, W. T. (1975). J. Am. Chem. Soc. 97, 1427–1439.  Google Scholar
 First citationDhifet, M., Belkhiria, M. S., Daran, J.-C. & Nasri, H. (2011). Acta Cryst. E67, m460–m461.  Google Scholar
 First citationGismelseed, A., Bominaar, E. L., Bill, E., Trautwein, A. X., Winkler, H., Nasri, H., Doppelt, P., Mandon, D., Fischer, J. & Weiss, R. (1990). Inorg. Chem. 29, 2741–2749.  CSD CrossRef CAS Web of Science Google Scholar
 First citationNasri, H., Ellison, M. K., Chen, S., Huynh, B. H. & Scheidt, W. R. (1997). J. Am. Chem. Soc. 119, 6274–6283.  Google Scholar
 First citationSchappacher, M., Ricard, L., Weiss, R., Montiel-Montoya, R., Gonser, U., Bill, E. & Trautwein, A. (1983). Inorg. Chim. Acta, 78, L9–L12.  CrossRef CAS Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSheldrick, G. M. (2015). Acta Cryst. C71, 3–8.  Web of Science CrossRef IUCr Journals Google Scholar

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ISSN: 2056-9890
Volume 71| Part 2| February 2015| Pages m42-m43
doi:10.1107/S205698901500153X
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