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The title complex, (diethyl 3,4,8,15,19,20-hexa­methyl-21,22,23,24-tetraazopenta­cyclo­[16.2.1.12,5.17,11.114,17]­tetracosa-1(20),2(22),3,5,7,9,11,13(24),14,16,18-undecaene-9,14-dicarb­oxyl­ate-κ4N)­iodo­iron(III) chloro­form solvate, [Fe(C32H32­N4O4)I]·­CHCl3, shows an almost planar arrangement of the corrphycene moiety with a slightly distorted trapezoid pyramidal core; the FeIII atom is 0.416 (1) Å from the plane of the C20N4 system. The Fe—N distances are 2.049 (3), 2.044 (3), 2.079 (3) and 2.075 (3) Å. The solvated chloro­form forms a C—H...O hydrogen bond [C...O 3.107 (10) Å] to an adjacent carbonyl O atom. This is the first X-ray structure analysis of a corrphycenatoiron(III) derivative.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270101003985/fg1624sup1.cif
Contains datablocks I, [Fe(6MeCn)I]

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270101003985/fg1624Isup2.hkl
Contains datablock I

CCDC reference: 166968

Comment top

Corrphycene is one of the porphyrin family and it is transcribed as [18]porphyrin-(2.1.0.1). Although the structure of various metallocorrphycenes has been reported (Sessler et al., 2000), little is known on the structure of iron corrphycene. In this paper, we describe the first example of an X-ray crystallographic analysis of iron(III) corrphycene complex, (I). \sch

The molecular structure of (I) with numbering is shown in Fig. 1. One of the ethoxycarbonyl groups is disordered. On the other hand, another ethoxycarbonyl group takes ordered structure because of the hydrogen bonding with an adjacent chloroform molecule. [C—H.·O hydrogen bonding; C33···O2 3.119 (11) Å] The corrphycene ring exhibits almost planar structure where the shifts of peripheral 24 atoms from the least-squares plane of the C20N4 corrphycenato core are within 0.059 (4) Å. The central N4 cavity shows trapezoidal geometry with N1···N2 2.464 (4), N2···N3 2.805 (5), N3···N4 3.308 (5), and N4···N1 2.811 (5) Å. Thus, the surface area within the N4 coordinating core is 8.015 Å2, which is smaller than the corresponding area of iron porphyrins; 8.123 Å2 in both [Fe(OEP)Cl] and [Fe(TPP)I] (OEP: dianion of 2,3,7,8,12,13,17,18-octaethylporphyrin (Cambridge Structural Database reference code TOYRUU; Senge, 1997; TPP: dianion of meso-tetraphenylporphyrin; Hatano & Scheidt, 1979). The axial Fe—I bond distance is 2.600 (1) Å, which is longer than that reported for [Fe(TPP)I], 2.55 Å. The Fe—N bond distances for direct-linked pyrroles, 2.044 (3) and 2.049 (3) Å, are slightly shorter than those for etheno-bridged pyrroles, 2.080 (3) and 2.075 (3) Å; the average Fe—N bond distance is 2.07 Å in both [Fe(OEP)Cl] and [Fe(TPP)I]. The deviation of the central iron(III) atom from the least-squares plane of the C20N4, 0.416 (1) Å, is significantly smaller than that of [Fe(TPP)I], 0.526 Å. These results clearly demonstrate the difference in cavity geometry between iron(III) corrphycene and iron(III) porphyrin complexes.

One of the two ethoxycarbonyl groups is disordered over two orientations; the other is not diordered and is locked in the conformation found in the crystal by a C—H···O hydrogen bond (see Fig. 1 and Table 2) with the chloroform of solvation.

Related literature top

For related literature, see: Adler et al. (1970); Hatano & Scheidt (1979); Maricondi et al. (1969); Neya et al. (1998); Senge (1997); Sessler et al. (2000).

Experimental top

12,17-Bis(ethoxycarbonyl)-2,3,6,7,11,18-hexamethylcorrphycene was synthesized according to the reported method (Neya et al., 1998). Insertion of iron was carried out after Adler (Adler et al., 1970). The chloro iron(III) complex thus obtained was converted to the title complex by cleaving of the µ-oxo-bridged dimers (Maricondi et al., 1969). The solid was recrystallized from chloroform solution.

Refinement top

There is a disorder in one of the two ethoxycarbonyl groups. The site occupation factor for disordered groups (A and B) are A:B = 0.50:0.50. H atoms were refined using a riding model. The positional parameters of H atoms were constrained to have the C—H distances of 0.96 Å for primary, 0.97 Å for secondary, and 0.93 Å for aromatic. Hydrogen U values constrained to 1.2 times the equivalent isotropic U of the atoms to which they are attached (1.5 for methyl groups).

Computing details top

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1992a); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: MSC/AFC Diffractometer Control Software and TEXSAN (Molecular Structure Corporation, 1992b); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SV (Nemoto & Ohashi, 1993); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. The molecular structure (ORTEP; Johnson, 1965) of the title compound with atomic numbering. Displacement ellipsoids are shown at the 30% probability level. Hydrogen atoms are omitted for clarity.
(I) top
Crystal data top
[Fe(C32H32N4O4)I]·CHCl3Z = 2
Mr = 838.73F(000) = 842
Triclinic, P1Dx = 1.608 Mg m3
a = 8.538 (2) ÅMo Kα radiation, λ = 0.71069 Å
b = 14.114 (2) ÅCell parameters from 25 reflections
c = 15.648 (4) Åθ = 15.1–17.0°
α = 106.040 (14)°µ = 1.60 mm1
β = 93.59 (2)°T = 298 K
γ = 104.964 (16)°Prismatic, purple
V = 1732.5 (7) Å30.5 × 0.4 × 0.1 mm
Data collection top
RIGAKU AFC7
diffractometer
5539 reflections with I > 2σ(I)
Radiation source: rotating anodeRint = 0.020
Graphite monochromatorθmax = 27.5°, θmin = 2.5°
ω/2θ scansh = 011
Absorption correction: ψ scan
(North et al., 1968)
k = 1817
Tmin = 0.474, Tmax = 0.852l = 2020
8460 measured reflections3 standard reflections every 100 reflections
7927 independent reflections intensity decay: 0.9%
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)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.150H-atom parameters constrained
S = 1.09Calculated w = 1/[σ2(Fo2) + (0.0825P)2 + 0.6822P]
where P = (Fo2 + 2Fc2)/3
7927 reflections(Δ/σ)max < 0.001
432 parametersΔρmax = 0.88 e Å3
16 restraintsΔρmin = 0.76 e Å3
Crystal data top
[Fe(C32H32N4O4)I]·CHCl3γ = 104.964 (16)°
Mr = 838.73V = 1732.5 (7) Å3
Triclinic, P1Z = 2
a = 8.538 (2) ÅMo Kα radiation
b = 14.114 (2) ŵ = 1.60 mm1
c = 15.648 (4) ÅT = 298 K
α = 106.040 (14)°0.5 × 0.4 × 0.1 mm
β = 93.59 (2)°
Data collection top
RIGAKU AFC7
diffractometer
5539 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)
Rint = 0.020
Tmin = 0.474, Tmax = 0.8523 standard reflections every 100 reflections
8460 measured reflections intensity decay: 0.9%
7927 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.04816 restraints
wR(F2) = 0.150H-atom parameters constrained
S = 1.09Δρmax = 0.88 e Å3
7927 reflectionsΔρmin = 0.76 e Å3
432 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. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
I10.81293 (4)0.85284 (2)0.18885 (2)0.05948 (13)
Fe10.56588 (7)0.86650 (4)0.09197 (4)0.03837 (14)
Cl10.3088 (8)1.3740 (4)0.5315 (4)0.289 (3)
Cl20.5752 (7)1.3062 (5)0.4842 (4)0.294 (3)
Cl30.4321 (8)1.2793 (4)0.6387 (2)0.240 (2)
O10.2120 (6)0.9080 (4)0.4548 (3)0.0870 (13)
O20.2729 (9)1.0548 (4)0.4253 (4)0.131 (2)
N20.4342 (4)0.7163 (2)0.0296 (2)0.0438 (7)
N30.3986 (4)0.8645 (3)0.1829 (2)0.0430 (7)
N40.6543 (4)1.0193 (2)0.0960 (2)0.0417 (7)
N10.6237 (4)0.8314 (2)0.0356 (2)0.0429 (7)
C50.4705 (5)0.6647 (3)0.0507 (3)0.0443 (9)
C60.3854 (6)0.5566 (3)0.0736 (3)0.0526 (10)
C70.2961 (5)0.5456 (3)0.0054 (4)0.0536 (11)
C80.3278 (5)0.6462 (3)0.0591 (3)0.0468 (9)
C90.2629 (5)0.6763 (3)0.1361 (3)0.0521 (10)
H90.19000.62460.15190.063*
C100.2945 (5)0.7765 (3)0.1936 (3)0.0495 (10)
C110.2261 (6)0.8021 (4)0.2751 (3)0.0558 (11)
C120.2891 (6)0.9037 (4)0.3142 (3)0.0547 (11)
C130.3976 (5)0.9442 (3)0.2569 (3)0.0464 (9)
C140.4830 (6)1.0487 (4)0.2793 (3)0.0547 (11)
H140.46141.08480.33450.066*
C150.5881 (6)1.1128 (3)0.2443 (3)0.0557 (11)
H150.61901.18010.28230.067*
C160.6627 (5)1.1051 (3)0.1663 (3)0.0461 (9)
C170.7696 (6)1.1946 (3)0.1492 (3)0.0524 (10)
C180.8242 (5)1.1629 (3)0.0708 (3)0.0481 (10)
C190.7517 (5)1.0531 (3)0.0364 (3)0.0419 (8)
C200.7831 (5)0.9936 (3)0.0440 (3)0.0457 (9)
H200.85081.02810.07680.055*
C10.7230 (5)0.8885 (3)0.0793 (3)0.0439 (9)
C20.7439 (6)0.8217 (4)0.1627 (3)0.0507 (10)
C30.6535 (6)0.7236 (4)0.1691 (3)0.0530 (10)
C40.5789 (5)0.7316 (3)0.0885 (3)0.0448 (9)
C230.3882 (7)0.4708 (3)0.1553 (4)0.0680 (14)
H23A0.32640.40620.14950.102*
H23B0.49940.47010.16060.102*
H23C0.34070.48130.20800.102*
C240.1883 (7)0.4487 (3)0.0045 (4)0.0684 (14)
H24A0.12330.40750.05230.103*
H24B0.11750.46520.04810.103*
H24C0.25470.41100.02400.103*
C250.0980 (8)0.7238 (5)0.3044 (4)0.0792 (17)
H25A0.15090.70090.34750.119*
H25B0.04400.66600.25300.119*
H25C0.01870.75550.33110.119*
C220.6363 (9)0.6265 (4)0.2469 (4)0.0818 (18)
H22A0.69030.64490.29440.123*
H22B0.52230.59240.26870.123*
H22C0.68540.58130.22630.123*
C210.8471 (7)0.8558 (4)0.2296 (3)0.0615 (12)
H21A0.95810.85670.21380.092*
H21B0.84430.92360.22870.092*
H21C0.80460.80870.28860.092*
C320.9379 (6)1.2245 (3)0.0233 (4)0.0612 (12)
H32A0.88661.27020.00510.092*
H32B0.96211.17870.02870.092*
H32C1.03771.26380.06320.092*
C260.2616 (8)0.9659 (5)0.4032 (4)0.0712 (15)
C270.1924 (10)0.9597 (6)0.5467 (4)0.093 (2)
H27A0.13331.01000.54720.111*
H27B0.29830.99440.58360.111*
C280.0979 (11)0.8768 (8)0.5805 (5)0.115 (3)
H28A0.01100.84880.54780.173*
H28B0.09260.90460.64320.173*
H28C0.15110.82340.57230.173*
O3A0.9583 (10)1.3614 (6)0.2133 (7)0.099 (2)0.502 (5)
O4A0.7218 (11)1.3304 (6)0.2598 (7)0.096 (2)0.502 (5)
C29A0.8220 (6)1.3025 (3)0.2094 (4)0.0732 (16)0.502 (5)
C30A1.0039 (18)1.4641 (7)0.2818 (7)0.107 (4)0.502 (5)
H30A0.91881.49680.27550.128*0.502 (5)
H30B1.10441.50610.26990.128*0.502 (5)
C31A1.0284 (15)1.4618 (8)0.3770 (6)0.145 (4)0.502 (5)
H31A1.07281.53120.41690.217*0.502 (5)
H31B1.10671.42390.38340.217*0.502 (5)
H31C0.92751.42970.39330.217*0.502 (5)
O3B0.8193 (13)1.3230 (6)0.2927 (5)0.099 (2)0.498 (5)
O4B0.8818 (14)1.3700 (6)0.1740 (6)0.096 (2)0.498 (5)
C29B0.8220 (6)1.3025 (3)0.2094 (4)0.0732 (16)0.498 (5)
C30B0.8511 (16)1.4321 (7)0.3468 (8)0.107 (4)0.498 (5)
H30C0.82431.47310.31060.128*0.498 (5)
H30D0.78991.43850.39730.128*0.498 (5)
C31B1.0284 (15)1.4618 (8)0.3770 (6)0.145 (4)0.498 (5)
H31D1.06091.40450.38610.217*0.498 (5)
H31E1.05811.51760.43230.217*0.498 (5)
H31F1.08811.48430.33190.217*0.498 (5)
C330.4069 (11)1.2867 (6)0.5335 (6)0.108 (3)
H330.33321.22010.49680.129*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.05369 (19)0.0609 (2)0.0673 (2)0.01455 (14)0.00409 (14)0.02766 (16)
Fe10.0407 (3)0.0312 (3)0.0427 (3)0.0046 (2)0.0113 (2)0.0147 (2)
Cl10.351 (7)0.207 (4)0.326 (7)0.156 (5)0.063 (6)0.065 (4)
Cl20.218 (5)0.304 (6)0.252 (5)0.029 (4)0.116 (4)0.010 (5)
Cl30.421 (8)0.247 (4)0.105 (2)0.170 (5)0.057 (3)0.067 (3)
O10.120 (4)0.101 (3)0.055 (2)0.041 (3)0.043 (2)0.033 (2)
O20.214 (7)0.091 (4)0.105 (4)0.054 (4)0.101 (5)0.030 (3)
N20.0459 (18)0.0314 (15)0.0506 (19)0.0025 (13)0.0119 (15)0.0138 (14)
N30.0439 (18)0.0436 (17)0.0455 (18)0.0104 (14)0.0143 (14)0.0202 (15)
N40.0419 (17)0.0351 (16)0.0479 (19)0.0057 (13)0.0085 (14)0.0170 (14)
N10.0469 (18)0.0348 (16)0.0455 (18)0.0045 (13)0.0131 (15)0.0151 (14)
C50.048 (2)0.0305 (18)0.052 (2)0.0068 (16)0.0104 (18)0.0126 (17)
C60.051 (2)0.034 (2)0.067 (3)0.0046 (17)0.000 (2)0.0146 (19)
C70.047 (2)0.034 (2)0.075 (3)0.0004 (17)0.003 (2)0.020 (2)
C80.042 (2)0.0371 (19)0.060 (3)0.0017 (16)0.0064 (18)0.0222 (18)
C90.048 (2)0.047 (2)0.063 (3)0.0032 (18)0.014 (2)0.027 (2)
C100.045 (2)0.053 (2)0.059 (3)0.0109 (18)0.0173 (19)0.031 (2)
C110.051 (2)0.073 (3)0.053 (3)0.016 (2)0.018 (2)0.033 (2)
C120.054 (3)0.066 (3)0.054 (3)0.020 (2)0.025 (2)0.029 (2)
C130.050 (2)0.051 (2)0.045 (2)0.0195 (18)0.0161 (18)0.0182 (18)
C140.062 (3)0.053 (2)0.052 (2)0.021 (2)0.021 (2)0.012 (2)
C150.069 (3)0.040 (2)0.054 (3)0.013 (2)0.011 (2)0.0083 (19)
C160.046 (2)0.0365 (19)0.053 (2)0.0071 (16)0.0035 (18)0.0148 (17)
C170.051 (2)0.034 (2)0.068 (3)0.0072 (17)0.003 (2)0.0143 (19)
C180.042 (2)0.0337 (19)0.070 (3)0.0054 (16)0.003 (2)0.0241 (19)
C190.0412 (19)0.0382 (19)0.049 (2)0.0061 (15)0.0082 (17)0.0222 (17)
C200.043 (2)0.046 (2)0.052 (2)0.0051 (17)0.0134 (18)0.0258 (18)
C10.042 (2)0.046 (2)0.045 (2)0.0090 (16)0.0108 (17)0.0190 (17)
C20.055 (2)0.054 (2)0.051 (2)0.019 (2)0.018 (2)0.022 (2)
C30.057 (3)0.054 (2)0.051 (2)0.019 (2)0.015 (2)0.017 (2)
C40.049 (2)0.039 (2)0.046 (2)0.0105 (17)0.0105 (18)0.0146 (17)
C230.076 (3)0.036 (2)0.076 (3)0.005 (2)0.000 (3)0.005 (2)
C240.062 (3)0.036 (2)0.103 (4)0.001 (2)0.015 (3)0.027 (3)
C250.074 (4)0.083 (4)0.088 (4)0.012 (3)0.037 (3)0.041 (3)
C220.111 (5)0.058 (3)0.069 (3)0.021 (3)0.039 (3)0.005 (3)
C210.068 (3)0.070 (3)0.056 (3)0.024 (2)0.028 (2)0.026 (2)
C320.059 (3)0.040 (2)0.081 (3)0.003 (2)0.008 (2)0.029 (2)
C260.092 (4)0.078 (4)0.058 (3)0.037 (3)0.036 (3)0.026 (3)
C270.105 (5)0.124 (6)0.053 (3)0.033 (4)0.032 (3)0.028 (4)
C280.113 (6)0.164 (8)0.073 (4)0.025 (6)0.043 (4)0.051 (5)
O3A0.105 (6)0.053 (3)0.089 (5)0.016 (4)0.000 (4)0.018 (3)
O4A0.120 (6)0.042 (3)0.091 (5)0.011 (4)0.009 (4)0.004 (3)
C29A0.081 (4)0.040 (3)0.089 (4)0.018 (3)0.013 (3)0.009 (3)
C30A0.111 (8)0.051 (5)0.129 (9)0.003 (5)0.020 (7)0.003 (5)
C31A0.179 (11)0.128 (8)0.097 (6)0.035 (7)0.006 (7)0.001 (6)
O3B0.105 (6)0.053 (3)0.089 (5)0.016 (4)0.000 (4)0.018 (3)
O4B0.120 (6)0.042 (3)0.091 (5)0.011 (4)0.009 (4)0.004 (3)
C29B0.081 (4)0.040 (3)0.089 (4)0.018 (3)0.013 (3)0.009 (3)
C30B0.111 (8)0.051 (5)0.129 (9)0.003 (5)0.020 (7)0.003 (5)
C31B0.179 (11)0.128 (8)0.097 (6)0.035 (7)0.006 (7)0.001 (6)
C330.133 (7)0.085 (5)0.101 (6)0.029 (5)0.035 (5)0.020 (4)
Geometric parameters (Å, º) top
I1—Fe12.600 (1)C20—H200.9300
Fe1—N12.044 (3)C1—C21.435 (6)
Fe1—N22.049 (3)C2—C31.373 (7)
Fe1—N42.075 (3)C2—C211.509 (6)
Fe1—N32.079 (3)C3—C41.438 (6)
Cl1—C331.665 (9)C3—C221.526 (7)
Cl2—C331.670 (9)C23—H23A0.9600
Cl3—C331.681 (9)C23—H23B0.9600
O1—C261.314 (7)C23—H23C0.9600
O1—C271.464 (7)C24—H24A0.9600
O2—C261.182 (7)C24—H24B0.9600
N2—C81.362 (5)C24—H24C0.9600
N2—C51.365 (5)C25—H25A0.9600
N3—C131.375 (5)C25—H25B0.9600
N3—C101.388 (5)C25—H25C0.9600
N4—C161.374 (5)C22—H22A0.9600
N4—C191.388 (5)C22—H22B0.9600
N1—C41.361 (5)C22—H22C0.9600
N1—C11.363 (5)C21—H21A0.9600
C5—C41.423 (5)C21—H21B0.9600
C5—C61.441 (5)C21—H21C0.9600
C6—C71.370 (7)C32—H32A0.9600
C6—C231.506 (7)C32—H32B0.9600
C7—C81.444 (6)C32—H32C0.9600
C7—C241.492 (6)C27—C281.485 (10)
C8—C91.364 (6)C27—H27A0.9700
C9—C101.397 (7)C27—H27B0.9700
C9—H90.9300C28—H28A0.9600
C10—C111.430 (6)C28—H28B0.9600
C11—C121.341 (7)C28—H28C0.9600
C11—C251.531 (7)O3A—C29A1.230 (7)
C12—C131.450 (6)O3A—C30A1.483 (8)
C12—C261.496 (7)O4A—C29A1.263 (7)
C13—C141.399 (6)C30A—C31A1.502 (9)
C14—C151.357 (7)C30A—H30A0.9700
C14—H140.9300C30A—H30B0.9700
C15—C161.403 (6)C31A—H31A0.9700
C15—H150.9300C31A—H31B0.9700
C16—C171.457 (6)C31A—H31D0.9600
C17—C181.342 (7)C31A—H31E0.9600
C17—C29A1.487 (6)C31A—H31F0.9600
C18—C191.441 (5)O3B—C30B1.482 (8)
C18—C321.504 (6)C30B—H30C0.9700
C19—C201.390 (6)C30B—H30D0.9700
C20—C11.374 (6)C33—H330.9800
N1—Fe1—N274.0 (1)N1—C4—C5112.6 (4)
N1—Fe1—N486.1 (1)N1—C4—C3109.9 (4)
N2—Fe1—N4152.6 (1)C5—C4—C3137.5 (4)
N1—Fe1—N3152.1 (1)C6—C23—H23A109.5
N2—Fe1—N385.6 (1)C6—C23—H23B109.5
N4—Fe1—N3105.6 (1)H23A—C23—H23B109.5
N1—Fe1—I1103.92 (10)C6—C23—H23C109.5
N2—Fe1—I1103.80 (10)H23A—C23—H23C109.5
N4—Fe1—I199.01 (10)H23B—C23—H23C109.5
N3—Fe1—I199.26 (10)C7—C24—H24A109.5
C26—O1—C27117.5 (5)C7—C24—H24B109.5
C8—N2—C5107.7 (3)H24A—C24—H24B109.5
C8—N2—Fe1131.9 (3)C7—C24—H24C109.5
C5—N2—Fe1119.5 (3)H24A—C24—H24C109.5
C13—N3—C10106.2 (3)H24B—C24—H24C109.5
C13—N3—Fe1126.8 (3)C11—C25—H25A109.5
C10—N3—Fe1125.2 (3)C11—C25—H25B109.5
C16—N4—C19106.6 (3)H25A—C25—H25B109.5
C16—N4—Fe1127.4 (3)C11—C25—H25C109.5
C19—N4—Fe1124.4 (3)H25A—C25—H25C109.5
C4—N1—C1107.6 (3)H25B—C25—H25C109.5
C4—N1—Fe1119.7 (3)C3—C22—H22A109.5
C1—N1—Fe1132.0 (3)C3—C22—H22B109.5
N2—C5—C4112.2 (3)H22A—C22—H22B109.5
N2—C5—C6109.9 (4)C3—C22—H22C109.5
C4—C5—C6137.8 (4)H22A—C22—H22C109.5
C7—C6—C5106.0 (4)H22B—C22—H22C109.5
C7—C6—C23125.3 (4)C2—C21—H21A109.5
C5—C6—C23128.7 (4)C2—C21—H21B109.5
C6—C7—C8107.5 (4)H21A—C21—H21B109.5
C6—C7—C24127.8 (5)C2—C21—H21C109.5
C8—C7—C24124.7 (5)H21A—C21—H21C109.5
N2—C8—C9121.0 (4)H21B—C21—H21C109.5
N2—C8—C7108.9 (4)C18—C32—H32A109.5
C9—C8—C7130.0 (4)C18—C32—H32B109.5
C8—C9—C10126.8 (4)H32A—C32—H32B109.5
C8—C9—H9116.6C18—C32—H32C109.5
C10—C9—H9116.6H32A—C32—H32C109.5
N3—C10—C9126.2 (4)H32B—C32—H32C109.5
N3—C10—C11109.9 (4)O2—C26—O1122.2 (5)
C9—C10—C11123.9 (4)O2—C26—C12126.2 (5)
C12—C11—C10107.1 (4)O1—C26—C12111.5 (5)
C12—C11—C25129.4 (5)O1—C27—C28105.5 (6)
C10—C11—C25123.5 (5)O1—C27—H27A110.6
C11—C12—C13108.0 (4)C28—C27—H27A110.6
C11—C12—C26127.2 (4)O1—C27—H27B110.6
C13—C12—C26124.8 (5)C28—C27—H27B110.6
N3—C13—C14129.2 (4)H27A—C27—H27B108.8
N3—C13—C12108.8 (4)C27—C28—H28A109.5
C14—C13—C12121.9 (4)C27—C28—H28B109.5
C15—C14—C13138.7 (4)H28A—C28—H28B109.5
C15—C14—H14110.7C27—C28—H28C109.5
C13—C14—H14110.7H28A—C28—H28C109.5
C14—C15—C16137.3 (4)H28B—C28—H28C109.5
C14—C15—H15111.4C29A—O3A—C30A117.9 (8)
C16—C15—H15111.4O3A—C29A—O4A120.9 (6)
N4—C16—C15129.3 (4)O3A—C29A—C17122.3 (6)
N4—C16—C17108.5 (4)O4A—C29A—C17116.7 (5)
C15—C16—C17122.1 (4)O3A—C30A—C31A114.4 (9)
C18—C17—C16108.3 (4)O3A—C30A—H30A108.7
C18—C17—C29A124.2 (4)C31A—C30A—H30A108.7
C16—C17—C29A127.4 (4)O3A—C30A—H30B108.7
C17—C18—C19106.7 (4)C31A—C30A—H30B108.7
C17—C18—C32129.4 (4)H30A—C30A—H30B107.6
C19—C18—C32123.8 (4)C30A—C31A—H31A109.7 (10)
N4—C19—C20127.5 (3)C30A—C31A—H31B109.8 (11)
N4—C19—C18109.8 (4)H31A—C31A—H31B107.8 (10)
C20—C19—C18122.7 (4)C30A—C31A—H31C110.4 (10)
C1—C20—C19125.9 (4)H31A—C31A—H31C109.9 (11)
C1—C20—H20117.1H31B—C31A—H31C109.2 (11)
C19—C20—H20117.1O3B—C30B—H31C95.5 (10)
N1—C1—C20121.3 (4)O3B—C30B—H30C111.4
N1—C1—C2109.1 (4)O3B—C30B—H30D111.4
C20—C1—C2129.6 (4)H30C—C30B—H30D109.3
C3—C2—C1107.4 (4)Cl1—C33—Cl2111.3 (6)
C3—C2—C21127.5 (4)Cl1—C33—Cl3109.3 (5)
C1—C2—C21125.2 (4)Cl2—C33—Cl3116.4 (7)
C2—C3—C4106.0 (4)Cl1—C33—H33106.4
C2—C3—C22126.5 (4)Cl2—C33—H33106.4
C4—C3—C22127.5 (4)Cl3—C33—H33106.4
N1—Fe1—N2—C8179.7 (4)C11—C12—C13—N30.2 (5)
N4—Fe1—N2—C8135.5 (4)C26—C12—C13—N3177.0 (5)
N3—Fe1—N2—C819.6 (4)C11—C12—C13—C14179.9 (4)
I1—Fe1—N2—C878.9 (4)C26—C12—C13—C142.7 (8)
N1—Fe1—N2—C512.5 (3)N3—C13—C14—C151.8 (10)
N4—Fe1—N2—C557.3 (5)C12—C13—C14—C15178.6 (6)
N3—Fe1—N2—C5173.3 (3)C13—C14—C15—C160.6 (12)
I1—Fe1—N2—C588.3 (3)C19—N4—C16—C15179.2 (5)
N1—Fe1—N3—C13138.3 (3)Fe1—N4—C16—C1513.4 (7)
N2—Fe1—N3—C13179.1 (4)C19—N4—C16—C170.2 (4)
N4—Fe1—N3—C1326.3 (4)Fe1—N4—C16—C17165.6 (3)
I1—Fe1—N3—C1375.8 (3)C14—C15—C16—N43.0 (10)
N1—Fe1—N3—C1059.4 (5)C14—C15—C16—C17178.1 (6)
N2—Fe1—N3—C1016.8 (3)N4—C16—C17—C180.2 (5)
N4—Fe1—N3—C10171.4 (3)C15—C16—C17—C18178.9 (4)
I1—Fe1—N3—C1086.5 (3)N4—C16—C17—C29A176.2 (4)
N1—Fe1—N4—C16179.7 (4)C15—C16—C17—C29A2.9 (7)
N2—Fe1—N4—C16137.5 (4)C16—C17—C18—C190.5 (5)
N3—Fe1—N4—C1626.1 (4)C29A—C17—C18—C19176.6 (4)
I1—Fe1—N4—C1676.3 (3)C16—C17—C18—C32179.6 (4)
N1—Fe1—N4—C1916.3 (3)C29A—C17—C18—C323.5 (8)
N2—Fe1—N4—C1959.1 (5)C16—N4—C19—C20178.9 (4)
N3—Fe1—N4—C19170.5 (3)Fe1—N4—C19—C2012.6 (6)
I1—Fe1—N4—C1987.2 (3)C16—N4—C19—C180.6 (4)
N2—Fe1—N1—C412.0 (3)Fe1—N4—C19—C18165.8 (3)
N4—Fe1—N1—C4173.1 (3)C17—C18—C19—N40.7 (5)
N3—Fe1—N1—C456.6 (5)C32—C18—C19—N4179.5 (4)
I1—Fe1—N1—C488.6 (3)C17—C18—C19—C20179.1 (4)
N2—Fe1—N1—C1178.5 (4)C32—C18—C19—C201.0 (7)
N4—Fe1—N1—C117.5 (4)N4—C19—C20—C10.5 (7)
N3—Fe1—N1—C1133.9 (4)C18—C19—C20—C1177.7 (4)
I1—Fe1—N1—C180.8 (4)C4—N1—C1—C20177.4 (4)
C8—N2—C5—C4178.7 (4)Fe1—N1—C1—C2012.2 (6)
Fe1—N2—C5—C411.3 (5)C4—N1—C1—C20.9 (5)
C8—N2—C5—C60.7 (5)Fe1—N1—C1—C2169.5 (3)
Fe1—N2—C5—C6169.3 (3)C19—C20—C1—N10.5 (7)
N2—C5—C6—C70.8 (5)C19—C20—C1—C2177.5 (4)
C4—C5—C6—C7178.4 (5)N1—C1—C2—C30.9 (5)
N2—C5—C6—C23180.0 (5)C20—C1—C2—C3177.3 (5)
C4—C5—C6—C230.8 (9)N1—C1—C2—C21179.2 (4)
C5—C6—C7—C80.5 (5)C20—C1—C2—C212.7 (8)
C23—C6—C7—C8179.8 (4)C1—C2—C3—C40.4 (5)
C5—C6—C7—C24178.9 (5)C21—C2—C3—C4179.6 (5)
C23—C6—C7—C241.8 (8)C1—C2—C3—C22179.2 (5)
C5—N2—C8—C9176.6 (4)C21—C2—C3—C220.7 (9)
Fe1—N2—C8—C915.1 (6)C1—N1—C4—C5178.3 (4)
C5—N2—C8—C70.4 (5)Fe1—N1—C4—C59.9 (5)
Fe1—N2—C8—C7167.9 (3)C1—N1—C4—C30.7 (5)
C6—C7—C8—N20.1 (5)Fe1—N1—C4—C3171.1 (3)
C24—C7—C8—N2178.6 (4)N2—C5—C4—N10.9 (5)
C6—C7—C8—C9176.8 (5)C6—C5—C4—N1179.9 (5)
C24—C7—C8—C94.8 (8)N2—C5—C4—C3177.7 (5)
N2—C8—C9—C100.8 (7)C6—C5—C4—C31.5 (10)
C7—C8—C9—C10177.1 (5)C2—C3—C4—N10.1 (5)
C13—N3—C10—C9177.3 (4)C22—C3—C4—N1179.8 (5)
Fe1—N3—C10—C912.0 (6)C2—C3—C4—C5178.5 (5)
C13—N3—C10—C110.7 (5)C22—C3—C4—C51.2 (9)
Fe1—N3—C10—C11166.1 (3)C27—O1—C26—O28.4 (10)
C8—C9—C10—N30.0 (8)C27—O1—C26—C12175.3 (5)
C8—C9—C10—C11177.8 (5)C11—C12—C26—O2155.0 (8)
N3—C10—C11—C120.9 (5)C13—C12—C26—O228.3 (10)
C9—C10—C11—C12177.2 (5)C11—C12—C26—O121.0 (8)
N3—C10—C11—C25176.1 (5)C13—C12—C26—O1155.7 (5)
C9—C10—C11—C255.7 (8)C26—O1—C27—C28166.2 (6)
C10—C11—C12—C130.7 (5)C30A—O3A—C29A—O4A2.8 (13)
C25—C11—C12—C13176.1 (5)C30A—O3A—C29A—C17174.2 (9)
C10—C11—C12—C26176.5 (5)C18—C17—C29A—O3A29.6 (8)
C25—C11—C12—C266.7 (9)C16—C17—C29A—O3A145.8 (8)
C10—N3—C13—C14179.3 (5)C18—C17—C29A—O4A153.3 (7)
Fe1—N3—C13—C1414.3 (7)C16—C17—C29A—O4A31.3 (8)
C10—N3—C13—C120.3 (5)C29A—O3A—C30A—C31A68.9 (16)
Fe1—N3—C13—C12165.4 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C33—H33···O20.982.203.107 (10)154

Experimental details

Crystal data
Chemical formula[Fe(C32H32N4O4)I]·CHCl3
Mr838.73
Crystal system, space groupTriclinic, P1
Temperature (K)298
a, b, c (Å)8.538 (2), 14.114 (2), 15.648 (4)
α, β, γ (°)106.040 (14), 93.59 (2), 104.964 (16)
V3)1732.5 (7)
Z2
Radiation typeMo Kα
µ (mm1)1.60
Crystal size (mm)0.5 × 0.4 × 0.1
Data collection
DiffractometerRIGAKU AFC7
diffractometer
Absorption correctionψ scan
(North et al., 1968)
Tmin, Tmax0.474, 0.852
No. of measured, independent and
observed [I > 2σ(I)] reflections
8460, 7927, 5539
Rint0.020
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.048, 0.150, 1.09
No. of reflections7927
No. of parameters432
No. of restraints16
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.88, 0.76

Computer programs: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1992a), MSC/AFC Diffractometer Control Software and TEXSAN (Molecular Structure Corporation, 1992b), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 1997), SV (Nemoto & Ohashi, 1993), SHELXL97.

Selected geometric parameters (Å, º) top
I1—Fe12.600 (1)Fe1—N42.075 (3)
Fe1—N12.044 (3)Fe1—N32.079 (3)
Fe1—N22.049 (3)
N1—Fe1—N274.0 (1)N1—Fe1—N3152.1 (1)
N1—Fe1—N486.1 (1)N2—Fe1—N385.6 (1)
N2—Fe1—N4152.6 (1)N4—Fe1—N3105.6 (1)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C33—H33···O20.982.203.107 (10)153.8
 

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