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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 68| Part 2| February 2012| Page m180
doi:10.1107/S1600536812001766

All­yl(ferrocenylmeth­yl)di­methyl­ammonium perchlorate

Ying-Chun Wanga*

aCollege of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China
*Correspondence e-mail: wangyc33@yahoo.com.cn

(Received 8 January 2012; accepted 14 January 2012; online 21 January 2012)

The asymmetric unit of the title complex, [Fe(C5H5)(C11H17N)]ClO4, contains two independent all­yl(ferro­cenyl­meth­yl)dimethyl­ammonium cations and two ClO4− anions. The anions are disordered each over two sets of sites, with an occupancy ratio of 0.617 (6):0.383 (6). The distances from the Fe atoms to the centroids of the unsubstituted and substituted cyclo­penta­dienyl (Cp) rings are 1.645 (1)/1.657 (1) and 1.644 (1)/1.647 (1) Å. The dihedral angles between the two Cp rings are 2.49 (3) and 1.45 (4)° in the two ferrocenyl groups of the cations.

Related literature

For the ferroelectric properties of related amino derivatives, see: Fu et al. (2007[Fu, D.-W., Song, Y.-M., Wang, G.-X., Ye, Q., Xiong, R.-G., Akutagawa, T., Nakamura, T., Chan, P. W. H. & Huang, S. P. D. (2007). J. Am. Chem. Soc. 129, 5346-5347.], 2008[Fu, D.-W., Zhang, W. & Xiong, R.-G. (2008). Cryst. Growth Des. 8, 3461-3464.], 2009[Fu, D.-W., Ge, J.-Z., Dai, J., Ye, H.-Y. & Qu, Z.-R. (2009). Inorg. Chem. Commun. 12, 994-997.], 2011a[Fu, D.-W., Zhang, W., Cai, H.-L., Ge, J.-Z., Zhang, Y. & Xiong, R.-G. (2011a). Adv. Mater. 23, 5658-5662.],b[Fu, D.-W., Zhang, W., Cai, H.-L., Zhang, Y., Ge, J.-Z., Xiong, R.-G. & Huang, S. P. D. (2011b). J. Am. Chem. Soc. 133, 12780-12786.],c[Fu, D.-W., Zhang, W., Cai, H.-L., Zhang, Y., Ge, J.-Z., Xiong, R.-G., Huang, S. P. D. & Nakamura, T. (2011c). Angew. Chem. Int. Ed. 50, 11947-11951.]); Fu & Xiong (2008[Fu, D.-W. & Xiong, R.-G. (2008). Dalton Trans. pp. 3946-3948.]). For a related compound, see: Chen et al. (2010[Chen, H., Miao, J., Zhu, P., Wang, D. & Nie, Y. (2010). Acta Cryst. E66, m22.]).

[Scheme 1]

Experimental

Crystal data

  • [Fe(C5H5)(C11H17N)]ClO4

  • Mr = 383.65

  • Monoclinic, P 21 /c

  • a = 15.165 (3) Å

  • b = 10.858 (2) Å

  • c = 25.976 (8) Å

  • β = 123.84 (2)°

  • V = 3552.7 (17) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 1.02 mm−1

  • T = 298 K

  • 0.10 × 0.03 × 0.03 mm
Data collection

  • Rigaku Mercury2 CCD diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2005[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.910, Tmax = 1.000

  • 35474 measured reflections

  • 8130 independent reflections

  • 4317 reflections with I > 2σ(I)

  • Rint = 0.097
Refinement

  • R[F2 > 2σ(F2)] = 0.065

  • wR(F2) = 0.167

  • S = 1.01

  • 8130 reflections

  • 500 parameters

  • 18 restraints

  • H-atom parameters constrained

  • Δρmax = 0.38 e Å−3

  • Δρmin = −0.32 e Å−3

Data collection: CrystalClear (Rigaku, 2005[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: XP in SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812001766/hy2506sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812001766/hy2506Isup2.hkl

checkCIF report


Comment top

Simple organic salts containing amino cations have attracted attention as materials, which display ferroelectric-paraelectric phase transitions (Fu et al., 2011a, b, c). With the purpose of obtaining phase transition crystals of amino compounds, various amines have been studied and a series of new materials with this kind of organic molecules have been elaborated (Fu et al. 2007, 2008, 2009; Fu & Xiong 2008). Herein we present the crystal structure of the title compound, which can be used as a cation in organic salts.

The asymmetric unit of the title compound contains two independent allyl(ferrocenylmethyl)dimethylammonium cations and two ClO4- anions. The anions are disordered each over two sets of sites, with an occupancy ratio of 0.617 (6):0.383 (6) (Fig. 1). The distances from the Fe atoms to the centroids of the unsubstituted and substituted cyclopentadienyl (Cp) rings are 1.645 (1) [1.657 (1) for another ferrocenyl group] and 1.644 (1) [1.647 (1)] Å. The dihedral angles between the two Cp rings are 2.49 (3) and 1.45 (4)° for the two ferrocenyl groups, respectively. The two Cp rings are almost eclipsed with the torsion angles of the two Cp rings (C—Cg1—Cg2—C and C—Cg3—Cg4—C) are in a range of 0.35 (5) to 1.69 (6) and 11.76 (7) to 14.49 (7)°, respectively. All bond lengths and angles are normal and comparable with those in a reported compound (Chen et al., 2010).

Related literature top

For the ferroelectric properties of related amino derivatives, see: Fu et al. (2007, 2008, 2009, 2011a,b,c); Fu & Xiong (2008). For a related compound, see: Chen et al. (2010).

Experimental top

A mixture of commercial allyl(ferrocenylmethyl)dimethylamine (0.4 mmol) and HClO4 (0.4 mmol) were dissolved in EtOH/distilled water (1:1 v/v). The solution was slowly evaporated in air, affording red block-shaped crystals of the title compound suitable for X-ray analysis.

The dielectric constant of title compound as a function of temperature indicates that the permittivity is basically temperature-independent, suggesting that this compound should not be a real ferroelectrics or there may be no distinct phase transition occurred within the measured temperature range. Similarly, below the melting point (423 K) of the compound, the dielectric constant as a function of temperature also goes smoothly, and there is no dielectric anomaly observed (dielectric constant ranging from 3.9 to 11.2).

Refinement top

H atoms attached to C atoms were positioned geometrically and treated as riding, with C—H = 0.97 (methylene), 0.98 (ferrocenyl), 0.93 (allyl) and 0.96 (methyl) Å and with Uiso(H) = 1.2(1.5 for methyl)Ueq(C). The ClO4- anions are each disordered over two sets of sites, with an occupancy ratio of 0.617 (6):0.383 (6) for both anions.

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level. H atoms and minor disordered atoms of the perchlorate anions have been omitted for clarity.
Allyl(ferrocenylmethyl)dimethylammonium perchlorate top
Crystal data top
[Fe(C5H5)(C11H17N)]ClO4F(000) = 1600
Mr = 383.65Dx = 1.434 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 8130 reflections
a = 15.165 (3) Åθ = 3.0–27.5°
b = 10.858 (2) ŵ = 1.02 mm−1
c = 25.976 (8) ÅT = 298 K
β = 123.84 (2)°Block, red
V = 3552.7 (17) Å30.10 × 0.03 × 0.03 mm
Z = 8
Data collection top
Rigaku Mercury2 CCD
diffractometer		8130 independent reflections
Radiation source: fine-focus sealed tube4317 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.097
Detector resolution: 13.6612 pixels mm-1θmax = 27.5°, θmin = 3.0°
ω scansh = −19→19
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)		k = −14→14
Tmin = 0.910, Tmax = 1.000l = −33→33
35474 measured reflections
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)] = 0.065Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.167H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0573P)2 + 1.691P]
where P = (Fo2 + 2Fc2)/3
8130 reflections(Δ/σ)max < 0.001
500 parametersΔρmax = 0.38 e Å−3
18 restraintsΔρmin = −0.32 e Å−3
Crystal data top
[Fe(C5H5)(C11H17N)]ClO4V = 3552.7 (17) Å3
Mr = 383.65Z = 8
Monoclinic, P21/cMo Kα radiation
a = 15.165 (3) ŵ = 1.02 mm−1
b = 10.858 (2) ÅT = 298 K
c = 25.976 (8) Å0.10 × 0.03 × 0.03 mm
β = 123.84 (2)°
Data collection top
Rigaku Mercury2 CCD
diffractometer		8130 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)		4317 reflections with I > 2σ(I)
Tmin = 0.910, Tmax = 1.000Rint = 0.097
35474 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.06518 restraints
wR(F2) = 0.167H-atom parameters constrained
S = 1.01Δρmax = 0.38 e Å−3
8130 reflectionsΔρmin = −0.32 e Å−3
500 parameters
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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)
Fe10.20107 (4)0.03124 (5)0.11383 (3)0.0524 (2)
N10.3530 (3)0.4015 (3)0.15949 (17)0.0648 (10)
C10.2102 (3)0.1552 (4)0.05836 (19)0.0578 (11)
H1A0.15230.20790.02730.069*
C20.2355 (4)0.0381 (5)0.0479 (2)0.0740 (14)
H2A0.1974−0.00600.00830.089*
C30.3226 (4)−0.0066 (4)0.1035 (3)0.0770 (15)
H3A0.3558−0.08740.10940.092*
C40.3540 (3)0.0827 (4)0.1504 (2)0.0666 (12)
H4A0.41340.07590.19390.080*
C50.2837 (3)0.1849 (4)0.12223 (19)0.0521 (10)
C60.1263 (6)0.0664 (6)0.1571 (4)0.0907 (17)
H6A0.13070.14370.17790.109*
C70.1932 (5)−0.0324 (7)0.1845 (2)0.0884 (17)
H7A0.2526−0.03800.22800.106*
C80.1604 (5)−0.1253 (5)0.1394 (4)0.0961 (18)
H8A0.1914−0.20750.14540.115*
C90.0727 (5)−0.0770 (7)0.0848 (3)0.097 (2)
H9A0.0314−0.11960.04490.116*
C100.0531 (4)0.0401 (7)0.0968 (3)0.0938 (19)
H10A−0.00430.09460.06680.113*
C110.2828 (3)0.2957 (4)0.1554 (2)0.0610 (11)
H11A0.30590.27190.19710.073*
H11B0.21040.32520.13460.073*
C120.3459 (4)0.5026 (5)0.1963 (3)0.0912 (17)
H12A0.38880.57090.19950.137*
H12B0.37090.47300.23710.137*
H12C0.27340.52880.17600.137*
C130.4665 (4)0.3602 (5)0.1931 (2)0.0823 (15)
H13A0.51010.42800.19650.124*
H13B0.47240.29440.17050.124*
H13C0.48960.33190.23380.124*
C140.3194 (4)0.4453 (5)0.0961 (2)0.0828 (15)
H14A0.37070.50520.10050.099*
H14B0.32080.37590.07300.099*
C150.2127 (6)0.5015 (7)0.0600 (3)0.116 (2)
H15A0.15540.45140.04980.140*
C160.1935 (7)0.6173 (7)0.0427 (3)0.145 (3)
H16A0.24870.67040.05200.174*
H16B0.12400.64600.02060.174*
Fe20.31426 (5)0.66103 (5)0.38832 (3)0.0577 (2)
N20.1454 (3)0.3021 (3)0.34554 (17)0.0661 (10)
C170.3271 (7)0.8145 (6)0.3495 (5)0.110 (2)
H17A0.28920.89220.34270.131*
C180.4220 (7)0.7851 (9)0.3991 (3)0.109 (2)
H18A0.46450.83780.43560.131*
C190.4507 (6)0.6724 (9)0.3925 (4)0.118 (3)
H19A0.51740.63020.42240.141*
C200.2927 (6)0.7162 (9)0.3082 (3)0.111 (2)
H20A0.22640.71200.26700.133*
C210.3704 (9)0.6271 (6)0.3356 (5)0.116 (3)
H21A0.36980.54760.31760.140*
C220.2254 (6)0.6969 (6)0.4232 (4)0.103 (2)
H22A0.20000.77840.42560.124*
C230.1718 (4)0.6162 (5)0.3733 (3)0.0792 (14)
H23A0.10230.63090.33500.095*
C240.2357 (3)0.5088 (4)0.3871 (2)0.0569 (11)
C250.3212 (6)0.6439 (6)0.4686 (3)0.102 (2)
H25A0.37460.68170.50840.123*
C260.3300 (4)0.5263 (5)0.4473 (2)0.0731 (13)
H26A0.38930.46840.46980.088*
C270.2137 (3)0.4046 (4)0.34492 (19)0.0584 (11)
H27A0.28090.36940.35590.070*
H27B0.17860.43610.30300.070*
C280.1349 (4)0.2021 (4)0.3024 (2)0.0844 (15)
H28A0.09280.13600.30250.127*
H28B0.20410.17170.31600.127*
H28C0.10100.23460.26120.127*
C290.0382 (4)0.3502 (5)0.3243 (3)0.107 (2)
H29A−0.00700.28300.31950.161*
H29B0.00820.39150.28530.161*
H29C0.04430.40710.35440.161*
C300.1952 (4)0.2503 (5)0.4106 (2)0.0807 (15)
H30A0.20620.31750.43820.097*
H30B0.14550.19340.41010.097*
C310.2962 (5)0.1868 (6)0.4359 (3)0.0953 (17)
H31A0.35220.23220.44060.114*
C320.3117 (6)0.0703 (6)0.4520 (3)0.128 (2)
H32A0.25750.02190.44800.154*
H32B0.37830.03620.46770.154*
Cl20.4518 (6)0.2080 (7)0.3465 (4)0.0600 (15)0.617 (6)
Cl10.0269 (7)0.4646 (9)0.1473 (4)0.141 (3)0.617 (6)
O50.5299 (16)0.220 (2)0.3347 (10)0.154 (7)0.617 (6)
O60.5069 (7)0.1523 (16)0.4056 (4)0.139 (4)0.617 (6)
O70.3739 (13)0.1372 (19)0.3074 (7)0.191 (8)0.617 (6)
O80.4272 (13)0.3283 (8)0.3485 (12)0.167 (7)0.617 (6)
O10.0203 (8)0.3776 (10)0.1042 (4)0.173 (4)0.617 (6)
O20.1362 (6)0.4198 (13)0.1996 (3)0.153 (4)0.617 (6)
O30.0544 (18)0.579 (2)0.166 (2)0.311 (8)0.617 (6)
O4−0.0535 (12)0.435 (2)0.1584 (13)0.192 (6)0.617 (6)
Cl2'0.4528 (16)0.2164 (19)0.3435 (11)0.108 (5)*0.383 (6)
Cl1'0.0375 (7)0.4629 (7)0.1546 (3)0.0577 (16)*0.383 (6)
O3'−0.0217 (13)0.5417 (16)0.0974 (5)0.154 (7)0.383 (6)
O8'0.3523 (15)0.276 (3)0.2971 (6)0.145 (7)0.383 (6)
O6'0.4711 (15)0.281 (3)0.3921 (9)0.162 (11)0.383 (6)
O7'0.408 (3)0.101 (2)0.341 (2)0.225 (19)0.383 (6)
O4'−0.014 (2)0.468 (4)0.180 (2)0.192 (6)0.383 (6)
O5'0.511 (2)0.199 (3)0.3184 (12)0.121 (11)0.383 (6)
O1'0.104 (3)0.547 (4)0.178 (3)0.311 (8)0.383 (6)
O2'0.0743 (17)0.3640 (18)0.1613 (10)0.175 (4)0.383 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.0552 (4)0.0534 (4)0.0562 (4)−0.0074 (3)0.0356 (3)−0.0046 (3)
N10.077 (2)0.061 (2)0.079 (3)−0.0210 (19)0.057 (2)−0.023 (2)
C10.059 (3)0.070 (3)0.054 (3)−0.009 (2)0.037 (2)0.001 (2)
C20.085 (4)0.078 (4)0.085 (4)−0.025 (3)0.063 (3)−0.029 (3)
C30.076 (3)0.057 (3)0.122 (5)0.002 (2)0.070 (4)−0.015 (3)
C40.049 (2)0.069 (3)0.080 (3)−0.006 (2)0.035 (2)−0.001 (3)
C50.053 (2)0.057 (3)0.059 (3)−0.0115 (19)0.039 (2)−0.009 (2)
C60.114 (5)0.090 (4)0.121 (5)−0.018 (4)0.098 (5)−0.013 (4)
C70.091 (4)0.112 (5)0.062 (3)−0.025 (4)0.042 (3)0.013 (3)
C80.123 (5)0.057 (3)0.146 (6)−0.009 (3)0.099 (5)0.014 (4)
C90.099 (5)0.129 (6)0.077 (4)−0.063 (4)0.058 (4)−0.034 (4)
C100.063 (3)0.126 (6)0.107 (5)0.003 (3)0.057 (4)0.042 (4)
C110.068 (3)0.060 (3)0.077 (3)−0.018 (2)0.054 (3)−0.017 (2)
C120.119 (4)0.077 (3)0.115 (4)−0.033 (3)0.088 (4)−0.043 (3)
C130.066 (3)0.095 (4)0.093 (4)−0.025 (3)0.048 (3)−0.019 (3)
C140.106 (4)0.070 (3)0.085 (4)−0.014 (3)0.062 (4)−0.008 (3)
C150.127 (6)0.091 (5)0.117 (5)−0.010 (4)0.059 (5)0.008 (4)
C160.171 (7)0.113 (6)0.117 (6)0.015 (5)0.058 (5)0.013 (5)
Fe20.0790 (5)0.0511 (4)0.0594 (4)−0.0075 (3)0.0487 (4)−0.0040 (3)
N20.076 (2)0.065 (2)0.080 (3)−0.0181 (19)0.058 (2)−0.023 (2)
C170.157 (7)0.065 (4)0.153 (7)0.006 (4)0.114 (6)0.031 (5)
C180.118 (6)0.139 (7)0.094 (5)−0.065 (5)0.073 (5)−0.030 (5)
C190.109 (5)0.143 (7)0.149 (8)0.033 (5)0.101 (6)0.056 (6)
C200.132 (6)0.142 (7)0.057 (4)−0.030 (5)0.052 (4)0.021 (4)
C210.228 (9)0.070 (4)0.155 (7)−0.037 (5)0.171 (7)−0.021 (5)
C220.153 (6)0.073 (4)0.153 (6)−0.025 (4)0.128 (6)−0.038 (4)
C230.079 (3)0.069 (3)0.111 (4)−0.004 (3)0.065 (3)−0.006 (3)
C240.069 (3)0.052 (3)0.069 (3)−0.008 (2)0.050 (3)−0.008 (2)
C250.164 (6)0.105 (5)0.073 (4)−0.072 (5)0.088 (4)−0.040 (4)
C260.090 (4)0.076 (3)0.053 (3)−0.020 (3)0.040 (3)0.003 (2)
C270.068 (3)0.057 (3)0.067 (3)−0.011 (2)0.048 (2)−0.009 (2)
C280.109 (4)0.074 (3)0.087 (4)−0.034 (3)0.065 (3)−0.041 (3)
C290.070 (3)0.107 (5)0.165 (6)−0.017 (3)0.078 (4)−0.027 (4)
C300.124 (5)0.063 (3)0.090 (4)−0.025 (3)0.081 (4)−0.021 (3)
C310.105 (5)0.088 (4)0.091 (4)−0.010 (4)0.054 (4)−0.003 (3)
C320.159 (6)0.087 (5)0.121 (5)−0.006 (4)0.068 (5)−0.003 (4)
Cl20.0578 (19)0.0518 (16)0.083 (3)0.0009 (10)0.0474 (18)−0.0096 (13)
Cl10.085 (3)0.143 (4)0.182 (6)0.034 (3)0.066 (3)−0.020 (3)
O50.139 (10)0.120 (9)0.28 (2)−0.016 (7)0.168 (13)−0.030 (10)
O60.143 (8)0.191 (10)0.073 (5)0.042 (8)0.054 (5)0.005 (6)
O70.175 (10)0.200 (18)0.118 (8)−0.128 (12)0.032 (8)−0.051 (9)
O80.148 (13)0.057 (5)0.33 (2)0.018 (6)0.157 (16)−0.008 (10)
O10.170 (8)0.194 (8)0.130 (7)0.023 (6)0.069 (7)−0.057 (7)
O20.086 (5)0.290 (13)0.072 (5)0.042 (7)0.036 (4)−0.015 (6)
O30.19 (2)0.130 (13)0.61 (3)0.012 (11)0.22 (2)−0.067 (16)
O40.106 (12)0.175 (13)0.35 (2)−0.039 (7)0.159 (15)−0.067 (10)
O3'0.172 (14)0.171 (14)0.074 (8)0.100 (12)0.041 (8)0.045 (9)
O8'0.109 (11)0.23 (2)0.095 (10)0.066 (12)0.057 (9)0.005 (11)
O6'0.100 (12)0.26 (3)0.092 (11)−0.018 (16)0.035 (10)−0.080 (15)
O7'0.39 (4)0.082 (11)0.41 (5)−0.058 (18)0.35 (5)−0.02 (2)
O4'0.106 (12)0.175 (13)0.35 (2)−0.037 (8)0.160 (15)−0.067 (10)
O5'0.16 (2)0.15 (2)0.123 (11)0.078 (17)0.123 (13)0.053 (13)
O1'0.19 (2)0.130 (13)0.61 (3)0.012 (11)0.22 (2)−0.067 (16)
O2'0.171 (8)0.194 (8)0.133 (7)0.024 (7)0.068 (7)−0.056 (8)
Geometric parameters (Å, º) top
Fe1—C52.024 (4)Fe2—C222.036 (5)
Fe1—C92.026 (5)Fe2—C252.038 (5)
Fe1—C72.026 (5)N2—C291.490 (6)
Fe1—C62.029 (5)N2—C281.503 (5)
Fe1—C12.032 (4)N2—C301.523 (6)
Fe1—C102.034 (5)N2—C271.527 (5)
Fe1—C42.035 (4)C17—C181.329 (9)
Fe1—C82.042 (5)C17—C201.393 (9)
Fe1—C32.046 (4)C17—H17A0.9800
Fe1—C22.051 (4)C18—C191.343 (9)
N1—C121.500 (5)C18—H18A0.9800
N1—C131.501 (6)C19—C211.379 (10)
N1—C141.505 (6)C19—H19A0.9800
N1—C111.528 (5)C20—C211.377 (9)
C1—C21.398 (6)C20—H20A0.9800
C1—C51.428 (5)C21—H21A0.9800
C1—H1A0.9800C22—C251.388 (8)
C2—C31.394 (7)C22—C231.390 (7)
C2—H2A0.9800C22—H22A0.9800
C3—C41.415 (6)C23—C241.428 (6)
C3—H3A0.9800C23—H23A0.9800
C4—C51.426 (6)C24—C261.428 (6)
C4—H4A0.9800C24—C271.478 (5)
C5—C111.484 (5)C25—C261.428 (7)
C6—C101.354 (8)C25—H25A0.9800
C6—C71.372 (8)C26—H26A0.9800
C6—H6A0.9800C27—H27A0.9700
C7—C81.410 (7)C27—H27B0.9700
C7—H7A0.9800C28—H28A0.9600
C8—C91.397 (8)C28—H28B0.9600
C8—H8A0.9800C28—H28C0.9600
C9—C101.380 (8)C29—H29A0.9600
C9—H9A0.9800C29—H29B0.9600
C10—H10A0.9800C29—H29C0.9600
C11—H11A0.9700C30—C311.460 (7)
C11—H11B0.9700C30—H30A0.9700
C12—H12A0.9600C30—H30B0.9700
C12—H12B0.9600C31—C321.312 (7)
C12—H12C0.9600C31—H31A0.9301
C13—H13A0.9600C32—H32A0.9301
C13—H13B0.9600C32—H32B0.9299
C13—H13C0.9600Cl2—O71.296 (13)
C14—C151.477 (8)Cl2—O81.367 (12)
C14—H14A0.9700Cl2—O51.386 (18)
C14—H14B0.9700Cl2—O61.412 (13)
C15—C161.313 (8)Cl1—O31.31 (3)
C15—H15A0.9299Cl1—O11.426 (11)
C16—H16A0.9300Cl1—O41.44 (2)
C16—H16B0.9300Cl1—O21.523 (11)
Fe2—C212.009 (14)Cl2'—O6'1.33 (2)
Fe2—C202.009 (5)Cl2'—O5'1.37 (3)
Fe2—C182.013 (6)Cl2'—O7'1.42 (3)
Fe2—C172.013 (5)Cl2'—O8'1.47 (2)
Fe2—C192.015 (6)Cl1'—O2'1.18 (2)
Fe2—C242.027 (4)Cl1'—O1'1.24 (5)
Fe2—C232.029 (5)Cl1'—O4'1.28 (4)
Fe2—C262.034 (4)Cl1'—O3'1.503 (15)
C5—Fe1—C9158.0 (3)C18—Fe2—C24166.4 (4)
C5—Fe1—C7121.9 (2)C17—Fe2—C24152.5 (3)
C9—Fe1—C767.0 (2)C19—Fe2—C24128.9 (3)
C5—Fe1—C6106.8 (2)C21—Fe2—C23129.4 (3)
C9—Fe1—C666.3 (2)C20—Fe2—C23109.3 (3)
C7—Fe1—C639.5 (2)C18—Fe2—C23151.9 (4)
C5—Fe1—C141.23 (16)C17—Fe2—C23119.5 (3)
C9—Fe1—C1123.5 (2)C19—Fe2—C23167.6 (4)
C7—Fe1—C1158.4 (2)C24—Fe2—C2341.21 (17)
C6—Fe1—C1123.2 (2)C21—Fe2—C26117.7 (3)
C5—Fe1—C10121.8 (2)C20—Fe2—C26151.4 (3)
C9—Fe1—C1039.7 (2)C18—Fe2—C26129.1 (3)
C7—Fe1—C1066.3 (2)C17—Fe2—C26165.8 (3)
C6—Fe1—C1038.9 (2)C19—Fe2—C26108.5 (2)
C1—Fe1—C10108.5 (2)C24—Fe2—C2641.17 (17)
C5—Fe1—C441.14 (16)C23—Fe2—C2668.8 (2)
C9—Fe1—C4160.4 (3)C21—Fe2—C22167.2 (4)
C7—Fe1—C4107.3 (2)C20—Fe2—C22129.6 (4)
C6—Fe1—C4122.2 (2)C18—Fe2—C22119.8 (3)
C1—Fe1—C468.86 (18)C17—Fe2—C22109.7 (3)
C10—Fe1—C4157.2 (3)C19—Fe2—C22151.5 (4)
C5—Fe1—C8158.8 (3)C24—Fe2—C2268.56 (19)
C9—Fe1—C840.2 (2)C23—Fe2—C2240.0 (2)
C7—Fe1—C840.6 (2)C26—Fe2—C2268.4 (2)
C6—Fe1—C867.2 (2)C21—Fe2—C25151.8 (4)
C1—Fe1—C8159.2 (3)C20—Fe2—C25166.7 (4)
C10—Fe1—C867.3 (2)C18—Fe2—C25110.1 (2)
C4—Fe1—C8123.3 (2)C17—Fe2—C25128.6 (3)
C5—Fe1—C368.33 (17)C19—Fe2—C25119.0 (3)
C9—Fe1—C3125.7 (3)C24—Fe2—C2568.71 (19)
C7—Fe1—C3124.2 (3)C23—Fe2—C2567.5 (2)
C6—Fe1—C3158.8 (3)C26—Fe2—C2541.1 (2)
C1—Fe1—C367.58 (19)C22—Fe2—C2539.8 (2)
C10—Fe1—C3161.1 (3)C29—N2—C28109.6 (4)
C4—Fe1—C340.59 (18)C29—N2—C30107.8 (4)
C8—Fe1—C3109.4 (2)C28—N2—C30110.0 (4)
C5—Fe1—C268.27 (17)C29—N2—C27110.3 (4)
C9—Fe1—C2110.5 (2)C28—N2—C27108.0 (3)
C7—Fe1—C2160.0 (3)C30—N2—C27111.1 (3)
C6—Fe1—C2159.5 (3)C18—C17—C20107.6 (6)
C1—Fe1—C240.06 (17)C18—C17—Fe270.7 (4)
C10—Fe1—C2125.4 (2)C20—C17—Fe269.6 (3)
C4—Fe1—C268.03 (19)C18—C17—H17A126.2
C8—Fe1—C2124.4 (2)C20—C17—H17A126.2
C3—Fe1—C239.77 (19)Fe2—C17—H17A126.2
C12—N1—C13108.3 (4)C17—C18—C19110.3 (7)
C12—N1—C14111.5 (4)C17—C18—Fe270.7 (3)
C13—N1—C14108.0 (4)C19—C18—Fe270.6 (4)
C12—N1—C11107.5 (3)C17—C18—H18A124.8
C13—N1—C11110.2 (3)C19—C18—H18A124.8
C14—N1—C11111.3 (3)Fe2—C18—H18A124.8
C2—C1—C5108.0 (4)C18—C19—C21107.9 (7)
C2—C1—Fe170.7 (3)C18—C19—Fe270.5 (4)
C5—C1—Fe169.1 (2)C21—C19—Fe269.7 (4)
C2—C1—H1A126.0C18—C19—H19A126.1
C5—C1—H1A126.0C21—C19—H19A126.1
Fe1—C1—H1A126.0Fe2—C19—H19A126.1
C3—C2—C1108.6 (4)C21—C20—C17107.1 (6)
C3—C2—Fe169.9 (3)C21—C20—Fe269.9 (3)
C1—C2—Fe169.2 (2)C17—C20—Fe269.9 (3)
C3—C2—H2A125.7C21—C20—H20A126.4
C1—C2—H2A125.7C17—C20—H20A126.4
Fe1—C2—H2A125.7Fe2—C20—H20A126.4
C2—C3—C4108.9 (4)C20—C21—C19107.1 (6)
C2—C3—Fe170.3 (3)C20—C21—Fe270.0 (7)
C4—C3—Fe169.3 (2)C19—C21—Fe270.2 (7)
C2—C3—H3A125.5C20—C21—H21A126.4
C4—C3—H3A125.5C19—C21—H21A126.4
Fe1—C3—H3A125.5Fe2—C21—H21A126.4
C3—C4—C5107.1 (4)C25—C22—C23108.8 (5)
C3—C4—Fe170.1 (3)C25—C22—Fe270.1 (3)
C5—C4—Fe169.0 (2)C23—C22—Fe269.7 (3)
C3—C4—H4A126.5C25—C22—H22A125.6
C5—C4—H4A126.5C23—C22—H22A125.6
Fe1—C4—H4A126.5Fe2—C22—H22A125.6
C4—C5—C1107.3 (4)C22—C23—C24108.6 (5)
C4—C5—C11125.3 (4)C22—C23—Fe270.3 (3)
C1—C5—C11127.1 (4)C24—C23—Fe269.3 (2)
C4—C5—Fe169.8 (2)C22—C23—H23A125.7
C1—C5—Fe169.7 (2)C24—C23—H23A125.7
C11—C5—Fe1121.7 (2)Fe2—C23—H23A125.7
C10—C6—C7109.2 (6)C23—C24—C26106.9 (4)
C10—C6—Fe170.7 (3)C23—C24—C27126.8 (4)
C7—C6—Fe170.1 (3)C26—C24—C27126.0 (4)
C10—C6—H6A125.4C23—C24—Fe269.5 (2)
C7—C6—H6A125.4C26—C24—Fe269.7 (2)
Fe1—C6—H6A125.4C27—C24—Fe2121.6 (3)
C6—C7—C8108.2 (5)C22—C25—C26108.7 (5)
C6—C7—Fe170.3 (3)C22—C25—Fe270.0 (3)
C8—C7—Fe170.3 (3)C26—C25—Fe269.3 (3)
C6—C7—H7A125.9C22—C25—H25A125.6
C8—C7—H7A125.9C26—C25—H25A125.6
Fe1—C7—H7A125.9Fe2—C25—H25A125.6
C9—C8—C7105.6 (5)C25—C26—C24106.9 (5)
C9—C8—Fe169.3 (3)C25—C26—Fe269.6 (3)
C7—C8—Fe169.1 (3)C24—C26—Fe269.2 (2)
C9—C8—H8A127.2C25—C26—H26A126.5
C7—C8—H8A127.2C24—C26—H26A126.5
Fe1—C8—H8A127.2Fe2—C26—H26A126.5
C10—C9—C8108.7 (5)C24—C27—N2115.1 (3)
C10—C9—Fe170.4 (3)C24—C27—H27A108.5
C8—C9—Fe170.5 (3)N2—C27—H27A108.5
C10—C9—H9A125.6C24—C27—H27B108.5
C8—C9—H9A125.6N2—C27—H27B108.5
Fe1—C9—H9A125.6H27A—C27—H27B107.5
C6—C10—C9108.3 (6)N2—C28—H28A109.5
C6—C10—Fe170.3 (3)N2—C28—H28B109.5
C9—C10—Fe169.8 (3)H28A—C28—H28B109.5
C6—C10—H10A125.8N2—C28—H28C109.5
C9—C10—H10A125.8H28A—C28—H28C109.5
Fe1—C10—H10A125.8H28B—C28—H28C109.5
C5—C11—N1114.8 (3)N2—C29—H29A109.5
C5—C11—H11A108.6N2—C29—H29B109.5
N1—C11—H11A108.6H29A—C29—H29B109.5
C5—C11—H11B108.6N2—C29—H29C109.5
N1—C11—H11B108.6H29A—C29—H29C109.5
H11A—C11—H11B107.6H29B—C29—H29C109.5
N1—C12—H12A109.5C31—C30—N2114.9 (4)
N1—C12—H12B109.5C31—C30—H30A108.5
H12A—C12—H12B109.5N2—C30—H30A108.5
N1—C12—H12C109.5C31—C30—H30B108.5
H12A—C12—H12C109.5N2—C30—H30B108.5
H12B—C12—H12C109.5H30A—C30—H30B107.5
N1—C13—H13A109.5C32—C31—C30123.8 (6)
N1—C13—H13B109.5C32—C31—H31A118.7
H13A—C13—H13B109.5C30—C31—H31A117.5
N1—C13—H13C109.5C31—C32—H32A121.2
H13A—C13—H13C109.5C31—C32—H32B118.8
H13B—C13—H13C109.5H32A—C32—H32B120.0
C15—C14—N1114.1 (4)O7—Cl2—O8116.6 (11)
C15—C14—H14A108.7O7—Cl2—O5113.6 (13)
N1—C14—H14A108.7O8—Cl2—O5101.6 (11)
C15—C14—H14B108.7O7—Cl2—O6109.1 (9)
N1—C14—H14B108.7O8—Cl2—O6112.2 (9)
H14A—C14—H14B107.6O5—Cl2—O6102.8 (10)
C16—C15—C14124.7 (7)O3—Cl1—O1141 (2)
C16—C15—H15A117.9O3—Cl1—O4105.6 (16)
C14—C15—H15A117.4O1—Cl1—O4108.4 (11)
C15—C16—H16A120.6O3—Cl1—O290.6 (14)
C15—C16—H16B119.4O1—Cl1—O293.1 (7)
H16A—C16—H16B120.0O4—Cl1—O2111.9 (13)
C21—Fe2—C2040.1 (3)O6'—Cl2'—O5'132 (2)
C21—Fe2—C1866.3 (3)O6'—Cl2'—O7'111 (2)
C20—Fe2—C1866.2 (3)O5'—Cl2'—O7'107 (2)
C21—Fe2—C1767.3 (3)O6'—Cl2'—O8'96.7 (17)
C20—Fe2—C1740.5 (3)O5'—Cl2'—O8'108.5 (19)
C18—Fe2—C1738.6 (3)O7'—Cl2'—O8'96 (2)
C21—Fe2—C1940.1 (3)O2'—Cl1'—O1'114.1 (17)
C20—Fe2—C1966.9 (3)O2'—Cl1'—O4'110 (2)
C18—Fe2—C1938.9 (3)O1'—Cl1'—O4'107 (3)
C17—Fe2—C1966.0 (3)O2'—Cl1'—O3'129.6 (12)
C21—Fe2—C24107.9 (2)O1'—Cl1'—O3'86 (3)
C20—Fe2—C24118.1 (3)O4'—Cl1'—O3'107 (2)
C5—Fe1—C1—C2119.0 (4)C21—Fe2—C17—C18−80.0 (5)
C9—Fe1—C1—C2−82.2 (4)C20—Fe2—C17—C18−118.1 (6)
C7—Fe1—C1—C2164.3 (5)C19—Fe2—C17—C18−36.2 (4)
C6—Fe1—C1—C2−163.9 (3)C24—Fe2—C17—C18−165.4 (5)
C10—Fe1—C1—C2−123.6 (4)C23—Fe2—C17—C18156.3 (5)
C4—Fe1—C1—C280.6 (3)C26—Fe2—C17—C1833.7 (12)
C8—Fe1—C1—C2−49.1 (7)C22—Fe2—C17—C18113.4 (5)
C3—Fe1—C1—C236.7 (3)C25—Fe2—C17—C1872.7 (6)
C9—Fe1—C1—C5158.8 (3)C21—Fe2—C17—C2038.1 (4)
C7—Fe1—C1—C545.3 (6)C18—Fe2—C17—C20118.1 (6)
C6—Fe1—C1—C577.1 (3)C19—Fe2—C17—C2081.9 (5)
C10—Fe1—C1—C5117.5 (3)C24—Fe2—C17—C20−47.3 (7)
C4—Fe1—C1—C5−38.4 (2)C23—Fe2—C17—C20−85.6 (5)
C8—Fe1—C1—C5−168.1 (5)C26—Fe2—C17—C20151.8 (9)
C3—Fe1—C1—C5−82.2 (3)C22—Fe2—C17—C20−128.5 (5)
C2—Fe1—C1—C5−119.0 (4)C25—Fe2—C17—C20−169.2 (5)
C5—C1—C2—C30.3 (5)C20—C17—C18—C19−0.5 (7)
Fe1—C1—C2—C3−59.0 (3)Fe2—C17—C18—C1959.7 (5)
C5—C1—C2—Fe159.2 (3)C20—C17—C18—Fe2−60.1 (4)
C5—Fe1—C2—C381.8 (3)C21—Fe2—C18—C1782.8 (5)
C9—Fe1—C2—C3−121.7 (4)C20—Fe2—C18—C1738.8 (4)
C7—Fe1—C2—C3−42.9 (7)C19—Fe2—C18—C17120.9 (7)
C6—Fe1—C2—C3161.5 (6)C24—Fe2—C18—C17150.2 (8)
C1—Fe1—C2—C3120.2 (4)C23—Fe2—C18—C17−47.9 (7)
C10—Fe1—C2—C3−163.9 (4)C26—Fe2—C18—C17−169.9 (4)
C4—Fe1—C2—C337.3 (3)C22—Fe2—C18—C17−84.6 (5)
C8—Fe1—C2—C3−78.9 (4)C25—Fe2—C18—C17−127.4 (5)
C5—Fe1—C2—C1−38.4 (3)C21—Fe2—C18—C19−38.1 (5)
C9—Fe1—C2—C1118.1 (4)C20—Fe2—C18—C19−82.1 (5)
C7—Fe1—C2—C1−163.0 (5)C17—Fe2—C18—C19−120.9 (7)
C6—Fe1—C2—C141.3 (7)C24—Fe2—C18—C1929.3 (12)
C10—Fe1—C2—C176.0 (4)C23—Fe2—C18—C19−168.8 (5)
C4—Fe1—C2—C1−82.9 (3)C26—Fe2—C18—C1969.2 (6)
C8—Fe1—C2—C1161.0 (3)C22—Fe2—C18—C19154.5 (5)
C3—Fe1—C2—C1−120.2 (4)C25—Fe2—C18—C19111.7 (6)
C1—C2—C3—C4−0.1 (5)C17—C18—C19—C210.2 (7)
Fe1—C2—C3—C4−58.7 (3)Fe2—C18—C19—C2159.9 (4)
C1—C2—C3—Fe158.5 (3)C17—C18—C19—Fe2−59.7 (4)
C5—Fe1—C3—C2−81.6 (3)C21—Fe2—C19—C18118.6 (6)
C9—Fe1—C3—C279.0 (4)C20—Fe2—C19—C1880.2 (5)
C7—Fe1—C3—C2163.7 (3)C17—Fe2—C19—C1835.8 (4)
C6—Fe1—C3—C2−162.1 (6)C24—Fe2—C19—C18−171.5 (4)
C1—Fe1—C3—C2−37.0 (3)C23—Fe2—C19—C18154.8 (10)
C10—Fe1—C3—C244.5 (8)C26—Fe2—C19—C18−130.1 (5)
C4—Fe1—C3—C2−120.2 (4)C22—Fe2—C19—C18−51.5 (8)
C8—Fe1—C3—C2120.9 (3)C25—Fe2—C19—C18−86.5 (5)
C5—Fe1—C3—C438.6 (3)C20—Fe2—C19—C21−38.4 (4)
C9—Fe1—C3—C4−160.8 (3)C18—Fe2—C19—C21−118.6 (6)
C7—Fe1—C3—C4−76.1 (4)C17—Fe2—C19—C21−82.7 (5)
C6—Fe1—C3—C4−41.9 (7)C24—Fe2—C19—C2169.9 (5)
C1—Fe1—C3—C483.2 (3)C23—Fe2—C19—C2136.2 (14)
C10—Fe1—C3—C4164.7 (6)C26—Fe2—C19—C21111.3 (5)
C8—Fe1—C3—C4−118.9 (4)C22—Fe2—C19—C21−170.0 (6)
C2—Fe1—C3—C4120.2 (4)C25—Fe2—C19—C21155.0 (5)
C2—C3—C4—C5−0.1 (5)C18—C17—C20—C210.6 (7)
Fe1—C3—C4—C5−59.4 (3)Fe2—C17—C20—C21−60.3 (4)
C2—C3—C4—Fe159.3 (3)C18—C17—C20—Fe260.8 (4)
C5—Fe1—C4—C3−118.2 (4)C18—Fe2—C20—C2181.0 (5)
C9—Fe1—C4—C352.9 (7)C17—Fe2—C20—C21117.9 (6)
C7—Fe1—C4—C3122.7 (4)C19—Fe2—C20—C2138.3 (4)
C6—Fe1—C4—C3163.4 (4)C24—Fe2—C20—C21−84.7 (5)
C1—Fe1—C4—C3−79.8 (3)C23—Fe2—C20—C21−129.0 (5)
C10—Fe1—C4—C3−167.3 (5)C26—Fe2—C20—C21−48.1 (7)
C8—Fe1—C4—C381.1 (4)C22—Fe2—C20—C21−169.2 (4)
C2—Fe1—C4—C3−36.6 (3)C25—Fe2—C20—C21157.3 (11)
C9—Fe1—C4—C5171.1 (5)C21—Fe2—C20—C17−117.9 (6)
C7—Fe1—C4—C5−119.0 (3)C18—Fe2—C20—C17−36.9 (4)
C6—Fe1—C4—C5−78.3 (4)C19—Fe2—C20—C17−79.5 (5)
C1—Fe1—C4—C538.5 (2)C24—Fe2—C20—C17157.4 (4)
C10—Fe1—C4—C5−49.1 (6)C23—Fe2—C20—C17113.1 (5)
C8—Fe1—C4—C5−160.7 (3)C26—Fe2—C20—C17−166.0 (5)
C3—Fe1—C4—C5118.2 (4)C22—Fe2—C20—C1772.9 (5)
C2—Fe1—C4—C581.7 (3)C25—Fe2—C20—C1739.4 (13)
C3—C4—C5—C10.2 (4)C17—C20—C21—C19−0.4 (7)
Fe1—C4—C5—C1−59.9 (3)Fe2—C20—C21—C19−60.7 (4)
C3—C4—C5—C11175.3 (4)C17—C20—C21—Fe260.3 (4)
Fe1—C4—C5—C11115.2 (4)C18—C19—C21—C200.2 (7)
C3—C4—C5—Fe160.1 (3)Fe2—C19—C21—C2060.6 (4)
C2—C1—C5—C4−0.3 (4)C18—C19—C21—Fe2−60.4 (4)
Fe1—C1—C5—C459.9 (3)C18—Fe2—C21—C20−80.6 (5)
C2—C1—C5—C11−175.2 (4)C17—Fe2—C21—C20−38.5 (4)
Fe1—C1—C5—C11−115.0 (4)C19—Fe2—C21—C20−117.6 (6)
C2—C1—C5—Fe1−60.3 (3)C24—Fe2—C21—C20112.6 (5)
C9—Fe1—C5—C4−172.0 (5)C23—Fe2—C21—C2071.8 (5)
C7—Fe1—C5—C479.6 (3)C26—Fe2—C21—C20156.2 (4)
C6—Fe1—C5—C4120.1 (3)C22—Fe2—C21—C2040.5 (12)
C1—Fe1—C5—C4−118.3 (3)C25—Fe2—C21—C20−169.2 (5)
C10—Fe1—C5—C4159.8 (3)C20—Fe2—C21—C19117.6 (6)
C8—Fe1—C5—C450.0 (6)C18—Fe2—C21—C1937.1 (4)
C3—Fe1—C5—C4−38.1 (3)C17—Fe2—C21—C1979.1 (5)
C2—Fe1—C5—C4−81.0 (3)C24—Fe2—C21—C19−129.8 (5)
C9—Fe1—C5—C1−53.7 (6)C23—Fe2—C21—C19−170.5 (4)
C7—Fe1—C5—C1−162.0 (3)C26—Fe2—C21—C19−86.1 (5)
C6—Fe1—C5—C1−121.6 (3)C22—Fe2—C21—C19158.2 (10)
C10—Fe1—C5—C1−81.9 (3)C25—Fe2—C21—C19−51.5 (7)
C4—Fe1—C5—C1118.3 (3)C21—Fe2—C22—C25158.6 (10)
C8—Fe1—C5—C1168.3 (5)C20—Fe2—C22—C25−168.5 (4)
C3—Fe1—C5—C180.3 (3)C18—Fe2—C22—C25−86.1 (5)
C2—Fe1—C5—C137.3 (3)C17—Fe2—C22—C25−127.3 (5)
C9—Fe1—C5—C1168.1 (6)C19—Fe2—C22—C25−51.6 (7)
C7—Fe1—C5—C11−40.2 (5)C24—Fe2—C22—C2582.1 (4)
C6—Fe1—C5—C110.2 (4)C23—Fe2—C22—C25119.9 (5)
C1—Fe1—C5—C11121.8 (5)C26—Fe2—C22—C2537.7 (3)
C10—Fe1—C5—C1140.0 (5)C21—Fe2—C22—C2338.6 (13)
C4—Fe1—C5—C11−119.8 (5)C20—Fe2—C22—C2371.5 (5)
C8—Fe1—C5—C11−69.9 (7)C18—Fe2—C22—C23154.0 (4)
C3—Fe1—C5—C11−157.9 (4)C17—Fe2—C22—C23112.8 (5)
C2—Fe1—C5—C11159.1 (4)C19—Fe2—C22—C23−171.5 (5)
C5—Fe1—C6—C10120.1 (4)C24—Fe2—C22—C23−37.9 (3)
C9—Fe1—C6—C10−37.6 (4)C26—Fe2—C22—C23−82.3 (4)
C7—Fe1—C6—C10−119.7 (5)C25—Fe2—C22—C23−119.9 (5)
C1—Fe1—C6—C1078.0 (4)C25—C22—C23—C24−0.6 (6)
C4—Fe1—C6—C10162.4 (4)Fe2—C22—C23—C2458.9 (3)
C8—Fe1—C6—C10−81.5 (4)C25—C22—C23—Fe2−59.4 (4)
C3—Fe1—C6—C10−166.7 (5)C21—Fe2—C23—C22−169.6 (5)
C2—Fe1—C6—C1047.5 (8)C20—Fe2—C23—C22−129.2 (5)
C5—Fe1—C6—C7−120.1 (4)C18—Fe2—C23—C22−53.8 (7)
C9—Fe1—C6—C782.1 (4)C17—Fe2—C23—C22−85.9 (5)
C1—Fe1—C6—C7−162.3 (3)C19—Fe2—C23—C22160.8 (11)
C10—Fe1—C6—C7119.7 (5)C24—Fe2—C23—C22119.9 (5)
C4—Fe1—C6—C7−77.8 (4)C26—Fe2—C23—C2281.3 (4)
C8—Fe1—C6—C738.2 (3)C25—Fe2—C23—C2236.9 (4)
C3—Fe1—C6—C7−47.0 (7)C21—Fe2—C23—C2470.5 (5)
C2—Fe1—C6—C7167.2 (5)C20—Fe2—C23—C24110.9 (4)
C10—C6—C7—C8−0.2 (6)C18—Fe2—C23—C24−173.6 (5)
Fe1—C6—C7—C8−60.4 (4)C17—Fe2—C23—C24154.3 (4)
C10—C6—C7—Fe160.2 (4)C19—Fe2—C23—C2441.0 (13)
C5—Fe1—C7—C677.3 (4)C26—Fe2—C23—C24−38.6 (3)
C9—Fe1—C7—C6−80.0 (4)C22—Fe2—C23—C24−119.9 (5)
C1—Fe1—C7—C643.8 (7)C25—Fe2—C23—C24−82.9 (3)
C10—Fe1—C7—C6−36.6 (4)C22—C23—C24—C260.4 (5)
C4—Fe1—C7—C6120.0 (4)Fe2—C23—C24—C2659.9 (3)
C8—Fe1—C7—C6−118.7 (5)C22—C23—C24—C27−174.2 (4)
C3—Fe1—C7—C6161.4 (4)Fe2—C23—C24—C27−114.8 (4)
C2—Fe1—C7—C6−166.9 (5)C22—C23—C24—Fe2−59.5 (4)
C5—Fe1—C7—C8−164.0 (3)C21—Fe2—C24—C23−130.1 (5)
C9—Fe1—C7—C838.7 (4)C20—Fe2—C24—C23−87.7 (4)
C6—Fe1—C7—C8118.7 (5)C18—Fe2—C24—C23167.1 (9)
C1—Fe1—C7—C8162.5 (5)C17—Fe2—C24—C23−54.9 (6)
C10—Fe1—C7—C882.1 (4)C19—Fe2—C24—C23−169.6 (4)
C4—Fe1—C7—C8−121.3 (4)C26—Fe2—C24—C23118.1 (4)
C3—Fe1—C7—C8−79.9 (4)C22—Fe2—C24—C2336.8 (3)
C2—Fe1—C7—C8−48.2 (7)C25—Fe2—C24—C2379.7 (4)
C6—C7—C8—C90.4 (6)C21—Fe2—C24—C26111.9 (5)
Fe1—C7—C8—C9−60.0 (3)C20—Fe2—C24—C26154.2 (4)
C6—C7—C8—Fe160.4 (4)C18—Fe2—C24—C2649.1 (10)
C5—Fe1—C8—C9157.2 (5)C17—Fe2—C24—C26−173.0 (5)
C7—Fe1—C8—C9116.9 (5)C19—Fe2—C24—C2672.4 (5)
C6—Fe1—C8—C979.6 (4)C23—Fe2—C24—C26−118.1 (4)
C1—Fe1—C8—C9−44.9 (7)C22—Fe2—C24—C26−81.3 (3)
C10—Fe1—C8—C937.3 (3)C25—Fe2—C24—C26−38.4 (3)
C4—Fe1—C8—C9−165.8 (4)C21—Fe2—C24—C27−8.7 (5)
C3—Fe1—C8—C9−122.8 (4)C20—Fe2—C24—C2733.7 (5)
C2—Fe1—C8—C9−81.1 (4)C18—Fe2—C24—C27−71.5 (10)
C5—Fe1—C8—C740.2 (7)C17—Fe2—C24—C2766.4 (6)
C9—Fe1—C8—C7−116.9 (5)C19—Fe2—C24—C27−48.2 (5)
C6—Fe1—C8—C7−37.3 (3)C23—Fe2—C24—C27121.4 (5)
C1—Fe1—C8—C7−161.8 (5)C26—Fe2—C24—C27−120.6 (5)
C10—Fe1—C8—C7−79.6 (4)C22—Fe2—C24—C27158.1 (5)
C4—Fe1—C8—C777.3 (4)C25—Fe2—C24—C27−159.0 (5)
C3—Fe1—C8—C7120.3 (4)C23—C22—C25—C260.5 (6)
C2—Fe1—C8—C7162.0 (4)Fe2—C22—C25—C26−58.7 (3)
C7—C8—C9—C10−0.4 (6)C23—C22—C25—Fe259.2 (4)
Fe1—C8—C9—C10−60.4 (4)C21—Fe2—C25—C22−170.1 (5)
C7—C8—C9—Fe159.9 (3)C20—Fe2—C25—C2241.6 (12)
C5—Fe1—C9—C10−38.8 (7)C18—Fe2—C25—C22112.8 (5)
C7—Fe1—C9—C1080.1 (4)C17—Fe2—C25—C2273.5 (5)
C6—Fe1—C9—C1036.9 (3)C19—Fe2—C25—C22154.7 (5)
C1—Fe1—C9—C10−78.4 (4)C24—Fe2—C25—C22−81.6 (4)
C4—Fe1—C9—C10156.9 (6)C23—Fe2—C25—C22−37.1 (3)
C8—Fe1—C9—C10119.1 (5)C26—Fe2—C25—C22−120.1 (5)
C3—Fe1—C9—C10−163.4 (4)C21—Fe2—C25—C26−50.0 (7)
C2—Fe1—C9—C10−121.3 (4)C20—Fe2—C25—C26161.7 (10)
C5—Fe1—C9—C8−158.0 (5)C18—Fe2—C25—C26−127.1 (5)
C7—Fe1—C9—C8−39.0 (4)C17—Fe2—C25—C26−166.4 (4)
C6—Fe1—C9—C8−82.3 (4)C19—Fe2—C25—C26−85.2 (5)
C1—Fe1—C9—C8162.5 (3)C24—Fe2—C25—C2638.5 (3)
C10—Fe1—C9—C8−119.1 (5)C23—Fe2—C25—C2683.0 (3)
C4—Fe1—C9—C837.8 (8)C22—Fe2—C25—C26120.1 (5)
C3—Fe1—C9—C877.5 (4)C22—C25—C26—C24−0.2 (6)
C2—Fe1—C9—C8119.6 (4)Fe2—C25—C26—C24−59.4 (3)
C7—C6—C10—C9−0.1 (6)C22—C25—C26—Fe259.1 (4)
Fe1—C6—C10—C959.7 (4)C23—C24—C26—C25−0.1 (5)
C7—C6—C10—Fe1−59.8 (4)C27—C24—C26—C25174.6 (4)
C8—C9—C10—C60.4 (6)Fe2—C24—C26—C2559.7 (3)
Fe1—C9—C10—C6−60.1 (4)C23—C24—C26—Fe2−59.8 (3)
C8—C9—C10—Fe160.4 (4)C27—C24—C26—Fe2114.9 (4)
C5—Fe1—C10—C6−76.9 (4)C21—Fe2—C26—C25155.9 (5)
C9—Fe1—C10—C6119.1 (5)C20—Fe2—C26—C25−171.3 (6)
C7—Fe1—C10—C637.1 (4)C18—Fe2—C26—C2574.9 (5)
C1—Fe1—C10—C6−120.4 (4)C17—Fe2—C26—C2548.5 (11)
C4—Fe1—C10—C6−41.1 (7)C19—Fe2—C26—C25113.2 (5)
C8—Fe1—C10—C681.4 (4)C24—Fe2—C26—C25−118.3 (5)
C3—Fe1—C10—C6165.1 (6)C23—Fe2—C26—C25−79.7 (4)
C2—Fe1—C10—C6−161.5 (4)C22—Fe2—C26—C25−36.6 (3)
C5—Fe1—C10—C9164.0 (3)C21—Fe2—C26—C24−85.9 (4)
C7—Fe1—C10—C9−82.0 (4)C20—Fe2—C26—C24−53.1 (6)
C6—Fe1—C10—C9−119.1 (5)C18—Fe2—C26—C24−166.8 (4)
C1—Fe1—C10—C9120.5 (4)C17—Fe2—C26—C24166.7 (9)
C4—Fe1—C10—C9−160.2 (5)C19—Fe2—C26—C24−128.5 (4)
C8—Fe1—C10—C9−37.7 (3)C23—Fe2—C26—C2438.6 (3)
C3—Fe1—C10—C945.9 (8)C22—Fe2—C26—C2481.7 (3)
C2—Fe1—C10—C979.3 (4)C25—Fe2—C26—C24118.3 (5)
C4—C5—C11—N191.1 (5)C23—C24—C27—N2−87.9 (5)
C1—C5—C11—N1−94.8 (5)C26—C24—C27—N298.4 (5)
Fe1—C5—C11—N1177.8 (3)Fe2—C24—C27—N2−174.8 (3)
C12—N1—C11—C5−177.8 (4)C29—N2—C27—C2462.5 (5)
C13—N1—C11—C5−60.0 (5)C28—N2—C27—C24−177.7 (4)
C14—N1—C11—C559.9 (5)C30—N2—C27—C24−57.0 (5)
C12—N1—C14—C15−54.8 (6)C29—N2—C30—C31173.5 (4)
C13—N1—C14—C15−173.7 (4)C28—N2—C30—C3154.0 (5)
C11—N1—C14—C1565.2 (5)C27—N2—C30—C31−65.5 (5)
N1—C14—C15—C16115.3 (7)N2—C30—C31—C32−118.9 (6)

Experimental details

Crystal data
Chemical formula[Fe(C5H5)(C11H17N)]ClO4
Mr383.65
Crystal system, space groupMonoclinic, P21/c
Temperature (K)298
a, b, c (Å)15.165 (3), 10.858 (2), 25.976 (8)
β (°) 123.84 (2)
V (Å3)3552.7 (17)
Z8
Radiation typeMo Kα
µ (mm−1)1.02
Crystal size (mm)0.10 × 0.03 × 0.03
Data collection
DiffractometerRigaku Mercury2 CCD
diffractometer
Absorption correctionMulti-scan
(CrystalClear; Rigaku, 2005)
Tmin, Tmax0.910, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections		35474, 8130, 4317
Rint0.097
(sin θ/λ)max (Å−1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.065, 0.167, 1.01
No. of reflections8130
No. of parameters500
No. of restraints18
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.38, −0.32

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

 

Acknowledgements

This work was supported by the Doctoral Foundation of Southeast University, People's Republic of China.

References

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 First citationFu, D.-W., Zhang, W., Cai, H.-L., Zhang, Y., Ge, J.-Z., Xiong, R.-G., Huang, S. P. D. & Nakamura, T. (2011c). Angew. Chem. Int. Ed. 50, 11947–11951.  Web of Science CSD CrossRef CAS Google Scholar
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ISSN: 2056-9890
Volume 68| Part 2| February 2012| Page m180
doi:10.1107/S1600536812001766
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