PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2009 August 1; 65(Pt 8): m874.
Published online 2009 July 4. doi:  10.1107/S1600536809025057
PMCID: PMC2977100

(R,R)-N,N′-Bis(ferrocenylmeth­yl)cyclo­hexane-1,2-diamine

Abstract

In the structure of the title compound, [Fe2(C5H5)2(C18H24N2)], the cyclo­hexane ring has a chair configuration and the two ferrocenemethyl­amino groups are bonded to it equatorially, as expected. The configuration of the two ferrocence nuclei may be due to intra­molecular N—H(...)N hydrogen bonding involving the two NH groups.

Related literature

For the applications of ferrocene derivatives, see: Yang et al. (2002 [triangle]); Roberto et al. (2000 [triangle]); Beer (1998 [triangle]). For the crystal structures of related compounds, see: Hess et al. (1999 [triangle]); Base et al. (2002 [triangle]). For the synthetic strategy, see: Cho et al. (1999 [triangle]); Sutcliffe (2002 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0m874-scheme1.jpg

Experimental

Crystal data

  • [Fe2(C5H5)2(C18H24N2)]
  • M r = 510.27
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0m874-efi1.jpg
  • a = 5.9384 (7) Å
  • b = 10.5310 (11) Å
  • c = 19.173 (3) Å
  • β = 90.989 (10)°
  • V = 1198.9 (3) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 1.23 mm−1
  • T = 293 K
  • 0.15 × 0.12 × 0.10 mm

Data collection

  • Rigaku SCXmini diffractometer
  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 [triangle]) T min = 0.856, T max = 1.000 (expected range = 0.757–0.884)
  • 12081 measured reflections
  • 5474 independent reflections
  • 4717 reflections with I > 2σ(I)
  • R int = 0.044

Refinement

  • R[F 2 > 2σ(F 2)] = 0.042
  • wR(F 2) = 0.087
  • S = 1.06
  • 5474 reflections
  • 290 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.27 e Å−3
  • Δρmin = −0.45 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 2571 Friedel pairs
  • Flack parameter: 0.035 (19)

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809025057/su2124sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809025057/su2124Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

This work was supported by a start-up grant from Southeast University.

supplementary crystallographic information

Comment

The chemistry of ferrocene has received much attention as both ferrocene and its derivatives have applications in many fields. For example, ferrocene has been employed as a marker for the electrochemical detection of amino acids in selective anion sensors (Beer et al., 1998). It also has applications in catalysis (Yang et al., 2002), non-linear optical (NLO) materials (Roberto et al., 2000) and medicinal materials. As part of our continuing studies on new ferrocene compounds, we report herein on the crystal structure of the title compound,

R,R)—N1,N2-Cyclohexane-1,2-\ bis((ferrocenylmethylene)amine, (I).

The molecular structure of the title compound is illustrated in Fig. 1. It consists of (1R,2R)-cyclohexane-1,2-diamine units, in which the hydrogen atoms of the two amine groups have been substituted by ferrocenylmethyl units. The cyclohexane ring has a chair conformation and the two ferrocenemethylamino groups are equatorially bonded to it, with torsion angles C1—C11—N1—C12 and C19—C18—N2—C17 being 178.4 (3) and 168.3 (3)°, respectively. The bond lengths and angles and the conformation of the ferrocenyl group, are similar to those observed in other ferrocenemethylamino derivatives (Hess et al., 1999; Base et al., 2002). The Cp ring planes (C6—C10 and C19—C23), are inclined to one another by 48.84 (15)°. The intramolecular Fe—Fe distance is 7.6054 (11) Å, while the nearest intermolecular Fe—Fe separation is 5.9384 (7) Å. The orientation of the two ferrocence nuclei is probably due to the presence of the intramolecular N1—H1···N22 hydrogen bond (Table 1).

The crystal packing of the title compound is illustrated in Fig. 2.

Experimental

The title compound was synthesized by reducing the corresponding Schiff base (R,R)—N1,N2-Cyclohexane-1,2-bis((ferrocenylmethylene)) (5 mmol) (Cho et al., 1999), with sodium borohydride (40 mmol) in methanol, in an ice bath. 40 ml NaOH solution (1 mol.L-1) was added and the mixture was stirred at rt for an 1 h (Sutcliffe et al., 2002)). The mixture was extracted with CHCl3 and the solvent removed under vacumn. The crude product was purified by recrystalization from acetone. Red crystals, suitable for X-ray diffraction analysis, were obtained by slow evaporation of a methanol solution after 3 days.

Refinement

The H-atoms were included in calculated positions and treated as riding atoms: N—H = 0.86 Å, C—H = 0.93 - 0.97 Å, with Uiso(H) = 1.2Ueq(parent N- or C-atom).

Figures

Fig. 1.
A view of the molecular structure of the title compound, with the displacement ellipsoids were drawn at the 30% probability level.
Fig. 2.
A crystal packing diagram of the title compound, viewed along the a axis.

Crystal data

[Fe2(C5H5)2(C18H24N2)]F(000) = 536
Mr = 510.27Dx = 1.413 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 3140 reflections
a = 5.9384 (7) Åθ = 3.2–27.5°
b = 10.5310 (11) ŵ = 1.23 mm1
c = 19.173 (3) ÅT = 293 K
β = 90.989 (10)°Block, yellow
V = 1198.9 (3) Å30.15 × 0.12 × 0.10 mm
Z = 2

Data collection

Rigaku SCXmini diffractometer5474 independent reflections
Radiation source: fine-focus sealed tube4717 reflections with I > 2σ(I)
graphiteRint = 0.044
Detector resolution: 13.6612 pixels mm-1θmax = 27.5°, θmin = 3.2°
ω scansh = −7→7
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)k = −13→13
Tmin = 0.856, Tmax = 1.000l = −24→24
12081 measured reflections

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.042w = 1/[σ2(Fo2) + (0.0266P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.087(Δ/σ)max = 0.005
S = 1.06Δρmax = 0.27 e Å3
5474 reflectionsΔρmin = −0.45 e Å3
290 parametersExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraintExtinction coefficient: 0.0039 (6)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), 2567 Friedel pairs
Secondary atom site location: difference Fourier mapFlack parameter: 0.035 (19)

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles
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)

xyzUiso*/Ueq
Fe1−0.30550 (8)0.14014 (4)0.41771 (2)0.0319 (2)
Fe20.31701 (8)0.05780 (4)0.07731 (2)0.0359 (2)
N1−0.1496 (5)0.4290 (3)0.33760 (15)0.0420 (10)
N20.1430 (5)0.3628 (3)0.22723 (15)0.0424 (10)
C1−0.2745 (6)0.3278 (3)0.44519 (18)0.0346 (10)
C2−0.2197 (6)0.2484 (3)0.50262 (18)0.0379 (11)
C3−0.4105 (7)0.1713 (4)0.5177 (2)0.0439 (12)
C4−0.5809 (6)0.2026 (4)0.4685 (2)0.0455 (11)
C5−0.4994 (6)0.2994 (3)0.42391 (19)0.0392 (11)
C6−0.0664 (6)0.0033 (3)0.40032 (19)0.0433 (11)
C7−0.2839 (6)−0.0511 (3)0.4033 (2)0.0482 (11)
C8−0.4153 (7)0.0049 (4)0.3496 (2)0.0527 (14)
C9−0.2840 (7)0.0948 (4)0.3144 (2)0.0484 (14)
C10−0.0653 (6)0.0945 (3)0.34622 (18)0.0403 (11)
C11−0.1262 (6)0.4267 (3)0.41367 (18)0.0421 (11)
C12−0.0144 (7)0.5256 (3)0.30284 (19)0.0412 (11)
C13−0.1359 (8)0.6533 (4)0.3064 (2)0.0589 (14)
C14−0.0159 (9)0.7556 (4)0.2652 (2)0.069 (2)
C150.0105 (10)0.7148 (4)0.1895 (2)0.0685 (16)
C160.1400 (8)0.5900 (4)0.1867 (2)0.0578 (14)
C170.0245 (7)0.4849 (4)0.2277 (2)0.0427 (11)
C180.1208 (6)0.2940 (4)0.16031 (19)0.0484 (12)
C190.2803 (6)0.1851 (3)0.15736 (18)0.0363 (11)
C200.2432 (6)0.0588 (4)0.18120 (17)0.0405 (11)
C210.4394 (7)−0.0130 (4)0.1695 (2)0.0498 (12)
C220.5983 (6)0.0673 (4)0.13930 (18)0.0508 (13)
C230.5017 (6)0.1894 (4)0.13173 (19)0.0418 (11)
C240.0702 (7)0.0889 (4)0.0051 (2)0.0582 (14)
C250.0701 (7)−0.0383 (4)0.0239 (2)0.0531 (16)
C260.2822 (8)−0.0894 (5)0.0087 (2)0.0665 (17)
C270.4131 (7)0.0072 (7)−0.0203 (2)0.080 (2)
C280.2810 (9)0.1171 (6)−0.0231 (2)0.077 (2)
H1A−0.107200.352500.321400.0500*
H2A−0.074500.246200.527700.0450*
H2C0.290100.377600.235800.0510*
H3A−0.420600.107800.554900.0530*
H4A−0.731200.164300.465700.0550*
H5A−0.583200.339300.385300.0470*
H6A0.06100−0.017000.431500.0520*
H7A−0.33290−0.117000.435800.0580*
H8A−0.57340−0.015000.338800.0640*
H9A−0.333700.147800.275000.0580*
H10A0.062600.147500.332900.0480*
H11A−0.165200.509400.432200.0500*
H11B0.029500.409400.426600.0500*
H12A0.131500.532900.327200.0490*
H13A−0.288100.643500.288000.0710*
H13B−0.145300.679600.354700.0710*
H14A0.131400.771300.286100.0830*
H14B−0.101500.833900.267000.0830*
H15A−0.136800.704200.167600.0820*
H15B0.091000.779800.164100.0820*
H16A0.290800.602900.205700.0690*
H16B0.153400.563700.138400.0690*
H17A−0.123900.471200.205800.0510*
H18A0.150400.351900.122200.0580*
H18B−0.032200.263000.154600.0580*
H20A0.104100.026900.201700.0480*
H21A0.46100−0.102900.180800.0600*
H22A0.750800.043000.125800.0610*
H23A0.575500.264000.111900.0500*
H24A−0.056100.148100.009600.0700*
H25A−0.05550−0.084300.044600.0640*
H26A0.33020−0.177200.016900.0800*
H27A0.56820−0.00110−0.036400.0960*
H28A0.327800.19970−0.041300.0920*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Fe10.0361 (3)0.0313 (3)0.0283 (3)0.0006 (2)0.0029 (2)−0.0026 (2)
Fe20.0349 (3)0.0429 (3)0.0298 (3)0.0027 (3)−0.0002 (2)−0.0080 (2)
N10.063 (2)0.0298 (15)0.0337 (17)−0.0066 (14)0.0129 (14)−0.0055 (13)
N20.0559 (19)0.0376 (16)0.0339 (16)0.0043 (14)0.0064 (14)−0.0109 (13)
C10.0415 (18)0.0341 (18)0.0285 (18)0.0034 (15)0.0058 (14)−0.0078 (14)
C20.046 (2)0.041 (2)0.0267 (18)−0.0007 (17)0.0006 (15)−0.0047 (14)
C30.057 (2)0.043 (2)0.032 (2)−0.0020 (19)0.0139 (17)−0.0036 (16)
C40.0378 (18)0.049 (2)0.050 (2)−0.0018 (17)0.0097 (17)−0.0082 (18)
C50.0350 (17)0.0418 (19)0.041 (2)0.0060 (15)0.0048 (15)−0.0042 (16)
C60.049 (2)0.0328 (17)0.048 (2)0.0058 (16)0.0003 (17)−0.0036 (16)
C70.061 (2)0.0311 (19)0.053 (2)−0.0061 (17)0.013 (2)0.0020 (17)
C80.046 (2)0.054 (2)0.058 (3)−0.004 (2)−0.002 (2)−0.025 (2)
C90.066 (3)0.050 (2)0.0290 (19)0.016 (2)−0.0021 (17)−0.0073 (17)
C100.0485 (19)0.0336 (17)0.0393 (19)0.0017 (16)0.0127 (16)−0.0028 (15)
C110.053 (2)0.0363 (18)0.037 (2)−0.0050 (17)0.0055 (16)−0.0060 (15)
C120.060 (2)0.0322 (19)0.0317 (19)−0.0089 (17)0.0062 (17)−0.0033 (15)
C130.096 (3)0.039 (2)0.042 (2)0.005 (2)0.014 (2)−0.001 (2)
C140.130 (5)0.030 (2)0.047 (3)−0.006 (3)0.015 (3)−0.0015 (19)
C150.130 (4)0.035 (2)0.041 (2)−0.003 (3)0.019 (3)0.003 (2)
C160.089 (3)0.043 (2)0.042 (2)−0.010 (2)0.021 (2)0.0010 (18)
C170.057 (2)0.0331 (19)0.038 (2)−0.0017 (18)0.0055 (17)−0.0046 (16)
C180.057 (2)0.047 (2)0.041 (2)0.0072 (19)−0.0060 (19)−0.0137 (18)
C190.0371 (18)0.0406 (19)0.0314 (19)−0.0026 (16)0.0031 (15)−0.0064 (15)
C200.0461 (18)0.046 (2)0.0297 (17)−0.0076 (19)0.0055 (14)−0.0043 (17)
C210.061 (2)0.044 (2)0.044 (2)0.013 (2)−0.0119 (19)−0.0073 (18)
C220.0384 (18)0.075 (3)0.039 (2)0.011 (2)−0.0018 (15)−0.011 (2)
C230.0385 (18)0.050 (2)0.037 (2)−0.0132 (17)0.0007 (15)−0.0054 (16)
C240.061 (2)0.064 (3)0.049 (2)0.014 (2)−0.019 (2)−0.012 (2)
C250.049 (2)0.057 (3)0.053 (3)−0.006 (2)−0.0048 (18)−0.015 (2)
C260.069 (3)0.069 (3)0.061 (3)0.020 (3)−0.012 (3)−0.038 (3)
C270.042 (2)0.157 (6)0.041 (3)−0.008 (3)0.008 (2)−0.037 (3)
C280.102 (4)0.097 (4)0.030 (2)−0.041 (4)−0.013 (2)0.010 (2)

Geometric parameters (Å, °)

Fe1—C12.053 (3)C18—C191.489 (5)
Fe1—C22.045 (3)C19—C201.425 (5)
Fe1—C32.053 (4)C19—C231.412 (5)
Fe1—C42.028 (4)C20—C211.410 (6)
Fe1—C52.039 (3)C21—C221.400 (6)
Fe1—C62.054 (3)C22—C231.414 (6)
Fe1—C72.037 (3)C24—C281.404 (7)
Fe1—C82.032 (4)C24—C251.387 (6)
Fe1—C92.044 (4)C25—C261.405 (6)
Fe1—C102.052 (4)C26—C271.401 (8)
Fe2—C192.052 (3)C27—C281.399 (9)
Fe2—C202.047 (3)C2—H2A0.9800
Fe2—C212.041 (4)C3—H3A0.9800
Fe2—C222.036 (4)C4—H4A0.9800
Fe2—C232.043 (4)C5—H5A0.9800
Fe2—C242.025 (4)C6—H6A0.9800
Fe2—C252.042 (4)C7—H7A0.9800
Fe2—C262.041 (5)C8—H8A0.9800
Fe2—C272.037 (4)C9—H9A0.9800
Fe2—C282.032 (4)C10—H10A0.9800
N1—C111.463 (4)C11—H11A0.9700
N1—C121.464 (5)C11—H11B0.9700
N2—C171.466 (5)C12—H12A0.9800
N2—C181.477 (5)C13—H13A0.9700
N1—H1A0.9000C13—H13B0.9700
N2—H2C0.9000C14—H14A0.9700
C1—C51.422 (5)C14—H14B0.9700
C1—C111.498 (5)C15—H15A0.9700
C1—C21.416 (5)C15—H15B0.9700
C2—C31.428 (5)C16—H16A0.9700
C3—C41.411 (5)C16—H16B0.9700
C4—C51.421 (5)C17—H17A0.9800
C6—C101.414 (5)C18—H18A0.9700
C6—C71.415 (5)C18—H18B0.9700
C7—C81.410 (5)C20—H20A0.9800
C8—C91.406 (6)C21—H21A0.9800
C9—C101.425 (5)C22—H22A0.9800
C12—C171.525 (5)C23—H23A0.9800
C12—C131.528 (6)C24—H24A0.9800
C13—C141.521 (6)C25—H25A0.9800
C14—C151.524 (6)C26—H26A0.9800
C15—C161.524 (6)C27—H27A0.9800
C16—C171.527 (6)C28—H28A0.9800
C1—Fe1—C240.43 (13)N1—C12—C17109.2 (3)
C1—Fe1—C368.51 (15)C12—C13—C14112.0 (4)
C1—Fe1—C468.52 (15)C13—C14—C15110.6 (4)
C1—Fe1—C540.66 (14)C14—C15—C16109.7 (3)
C1—Fe1—C6131.14 (14)C15—C16—C17112.1 (4)
C1—Fe1—C7168.82 (15)N2—C17—C12109.5 (3)
C1—Fe1—C8150.00 (15)N2—C17—C16114.4 (3)
C1—Fe1—C9117.83 (15)C12—C17—C16111.1 (3)
C1—Fe1—C10109.67 (13)N2—C18—C19111.3 (3)
C2—Fe1—C340.78 (15)Fe2—C19—C18127.4 (3)
C2—Fe1—C468.20 (15)Fe2—C19—C2069.46 (19)
C2—Fe1—C568.17 (14)C20—C19—C23107.0 (3)
C2—Fe1—C6110.91 (14)C18—C19—C23125.8 (3)
C2—Fe1—C7130.07 (14)Fe2—C19—C2369.5 (2)
C2—Fe1—C8167.21 (15)C18—C19—C20127.2 (3)
C2—Fe1—C9152.01 (15)Fe2—C20—C2169.6 (2)
C2—Fe1—C10119.72 (14)C19—C20—C21108.5 (3)
C3—Fe1—C440.44 (16)Fe2—C20—C1969.86 (19)
C3—Fe1—C568.48 (16)Fe2—C21—C2070.1 (2)
C3—Fe1—C6119.06 (16)Fe2—C21—C2269.7 (2)
C3—Fe1—C7107.79 (16)C20—C21—C22107.9 (4)
C3—Fe1—C8127.81 (16)Fe2—C22—C2170.1 (2)
C3—Fe1—C9165.40 (17)Fe2—C22—C2370.0 (2)
C3—Fe1—C10152.51 (15)C21—C22—C23108.5 (3)
C4—Fe1—C540.90 (15)Fe2—C23—C2269.4 (2)
C4—Fe1—C6150.58 (15)C19—C23—C22108.3 (3)
C4—Fe1—C7116.05 (16)Fe2—C23—C1970.2 (2)
C4—Fe1—C8106.47 (16)C25—C24—C28108.0 (4)
C4—Fe1—C9127.28 (16)Fe2—C24—C2570.7 (2)
C4—Fe1—C10166.52 (15)Fe2—C24—C2870.0 (2)
C5—Fe1—C6168.25 (14)Fe2—C25—C2669.8 (3)
C5—Fe1—C7149.10 (14)C24—C25—C26108.2 (4)
C5—Fe1—C8116.02 (16)Fe2—C25—C2469.4 (2)
C5—Fe1—C9107.07 (16)Fe2—C26—C2569.9 (3)
C5—Fe1—C10129.14 (14)Fe2—C26—C2769.7 (3)
C6—Fe1—C740.46 (14)C25—C26—C27108.0 (4)
C6—Fe1—C867.61 (15)Fe2—C27—C2670.1 (2)
C6—Fe1—C967.91 (16)Fe2—C27—C2869.7 (3)
C6—Fe1—C1040.27 (14)C26—C27—C28107.5 (4)
C7—Fe1—C840.56 (16)Fe2—C28—C2770.1 (3)
C7—Fe1—C968.44 (16)C24—C28—C27108.3 (5)
C7—Fe1—C1068.39 (14)Fe2—C28—C2469.5 (2)
C8—Fe1—C940.37 (16)Fe1—C2—H2A126.00
C8—Fe1—C1068.02 (15)C1—C2—H2A126.00
C9—Fe1—C1040.73 (15)C3—C2—H2A126.00
C19—Fe2—C2040.68 (15)Fe1—C3—H3A126.00
C19—Fe2—C2168.39 (15)C2—C3—H3A126.00
C19—Fe2—C2268.16 (15)C4—C3—H3A126.00
C19—Fe2—C2340.35 (14)Fe1—C4—H4A126.00
C19—Fe2—C24108.70 (15)C3—C4—H4A126.00
C19—Fe2—C25127.88 (15)C5—C4—H4A126.00
C19—Fe2—C26165.27 (16)Fe1—C5—H5A126.00
C19—Fe2—C27153.3 (2)C1—C5—H5A126.00
C19—Fe2—C28119.8 (2)C4—C5—H5A126.00
C20—Fe2—C2140.36 (16)Fe1—C6—H6A126.00
C20—Fe2—C2267.60 (14)C7—C6—H6A126.00
C20—Fe2—C2367.76 (15)C10—C6—H6A126.00
C20—Fe2—C24119.99 (15)Fe1—C7—H7A126.00
C20—Fe2—C25109.06 (15)C6—C7—H7A126.00
C20—Fe2—C26127.59 (17)C8—C7—H7A126.00
C20—Fe2—C27164.5 (2)Fe1—C8—H8A126.00
C20—Fe2—C28154.1 (2)C7—C8—H8A125.00
C21—Fe2—C2240.17 (16)C9—C8—H8A125.00
C21—Fe2—C2368.00 (16)Fe1—C9—H9A126.00
C21—Fe2—C24153.37 (17)C8—C9—H9A126.00
C21—Fe2—C25119.68 (16)C10—C9—H9A126.00
C21—Fe2—C26108.14 (17)Fe1—C10—H10A126.00
C21—Fe2—C27126.8 (2)C6—C10—H10A126.00
C21—Fe2—C28164.40 (19)C9—C10—H10A126.00
C22—Fe2—C2340.58 (16)N1—C11—H11A109.00
C22—Fe2—C24165.45 (17)N1—C11—H11B109.00
C22—Fe2—C25153.11 (17)C1—C11—H11A109.00
C22—Fe2—C26119.11 (18)C1—C11—H11B109.00
C22—Fe2—C27108.01 (15)H11A—C11—H11B108.00
C22—Fe2—C28127.59 (19)N1—C12—H12A109.00
C23—Fe2—C24127.97 (16)C13—C12—H12A109.00
C23—Fe2—C25165.20 (16)C17—C12—H12A109.00
C23—Fe2—C26153.11 (17)C12—C13—H13A109.00
C23—Fe2—C27119.36 (19)C12—C13—H13B109.00
C23—Fe2—C28108.8 (2)C14—C13—H13A109.00
C24—Fe2—C2539.88 (17)C14—C13—H13B109.00
C24—Fe2—C2667.56 (18)H13A—C13—H13B108.00
C24—Fe2—C2767.98 (17)C13—C14—H14A109.00
C24—Fe2—C2840.49 (19)C13—C14—H14B109.00
C25—Fe2—C2640.25 (18)C15—C14—H14A110.00
C25—Fe2—C2767.65 (18)C15—C14—H14B110.00
C25—Fe2—C2867.3 (2)H14A—C14—H14B108.00
C26—Fe2—C2740.2 (2)C14—C15—H15A110.00
C26—Fe2—C2867.4 (2)C14—C15—H15B110.00
C27—Fe2—C2840.2 (2)C16—C15—H15A110.00
C11—N1—C12115.0 (3)C16—C15—H15B110.00
C17—N2—C18113.6 (3)H15A—C15—H15B108.00
C11—N1—H1A108.00C15—C16—H16A109.00
C12—N1—H1A108.00C15—C16—H16B109.00
C17—N2—H2C108.00C17—C16—H16A109.00
C18—N2—H2C108.00C17—C16—H16B109.00
C2—C1—C11126.6 (3)H16A—C16—H16B108.00
C5—C1—C11125.9 (3)N2—C17—H17A107.00
Fe1—C1—C569.15 (18)C12—C17—H17A107.00
Fe1—C1—C11128.1 (2)C16—C17—H17A107.00
Fe1—C1—C269.48 (18)N2—C18—H18A109.00
C2—C1—C5107.5 (3)N2—C18—H18B109.00
Fe1—C2—C170.09 (19)C19—C18—H18A109.00
Fe1—C2—C369.9 (2)C19—C18—H18B109.00
C1—C2—C3108.7 (3)H18A—C18—H18B108.00
Fe1—C3—C269.3 (2)Fe2—C20—H20A126.00
Fe1—C3—C468.8 (2)C19—C20—H20A126.00
C2—C3—C4107.1 (3)C21—C20—H20A126.00
Fe1—C4—C570.0 (2)Fe2—C21—H21A126.00
C3—C4—C5108.8 (3)C20—C21—H21A126.00
Fe1—C4—C370.7 (2)C22—C21—H21A126.00
C1—C5—C4107.8 (3)Fe2—C22—H22A126.00
Fe1—C5—C469.1 (2)C21—C22—H22A126.00
Fe1—C5—C170.19 (19)C23—C22—H22A126.00
Fe1—C6—C769.12 (19)Fe2—C23—H23A126.00
C7—C6—C10108.7 (3)C19—C23—H23A126.00
Fe1—C6—C1069.79 (19)C22—C23—H23A126.00
Fe1—C7—C869.5 (2)Fe2—C24—H24A126.00
C6—C7—C8107.2 (3)C25—C24—H24A126.00
Fe1—C7—C670.42 (19)C28—C24—H24A126.00
Fe1—C8—C769.9 (2)Fe2—C25—H25A126.00
Fe1—C8—C970.3 (2)C24—C25—H25A126.00
C7—C8—C9109.1 (4)C26—C25—H25A126.00
Fe1—C9—C869.4 (2)Fe2—C26—H26A126.00
C8—C9—C10107.6 (3)C25—C26—H26A126.00
Fe1—C9—C1070.0 (2)C27—C26—H26A126.00
Fe1—C10—C669.9 (2)Fe2—C27—H27A126.00
Fe1—C10—C969.3 (2)C26—C27—H27A126.00
C6—C10—C9107.5 (3)C28—C27—H27A126.00
N1—C11—C1111.6 (3)Fe2—C28—H28A126.00
C13—C12—C17111.7 (3)C24—C28—H28A126.00
N1—C12—C13109.2 (3)C27—C28—H28A126.00
C2—Fe1—C1—C5−119.1 (3)C26—Fe2—C21—C20−127.3 (3)
C2—Fe1—C1—C11121.0 (4)C26—Fe2—C21—C22113.9 (3)
C3—Fe1—C1—C237.6 (2)C27—Fe2—C21—C20−167.9 (3)
C3—Fe1—C1—C5−81.6 (2)C27—Fe2—C21—C2273.3 (3)
C3—Fe1—C1—C11158.5 (4)C19—Fe2—C22—C2181.9 (2)
C4—Fe1—C1—C281.2 (2)C19—Fe2—C22—C23−37.4 (2)
C4—Fe1—C1—C5−37.9 (2)C20—Fe2—C22—C2137.9 (2)
C4—Fe1—C1—C11−157.9 (3)C20—Fe2—C22—C23−81.5 (2)
C5—Fe1—C1—C2119.1 (3)C21—Fe2—C22—C23−119.4 (3)
C5—Fe1—C1—C11−119.9 (4)C23—Fe2—C22—C21119.4 (3)
C6—Fe1—C1—C2−72.9 (3)C25—Fe2—C22—C21−50.3 (4)
C6—Fe1—C1—C5168.0 (2)C25—Fe2—C22—C23−169.7 (3)
C6—Fe1—C1—C1148.1 (4)C26—Fe2—C22—C21−83.8 (3)
C8—Fe1—C1—C2167.0 (3)C26—Fe2—C22—C23156.8 (2)
C8—Fe1—C1—C547.9 (4)C27—Fe2—C22—C21−126.3 (3)
C8—Fe1—C1—C11−72.0 (5)C27—Fe2—C22—C23114.4 (3)
C9—Fe1—C1—C2−156.9 (2)C28—Fe2—C22—C21−166.5 (3)
C9—Fe1—C1—C584.0 (2)C28—Fe2—C22—C2374.1 (3)
C9—Fe1—C1—C11−36.0 (4)C19—Fe2—C23—C22119.4 (3)
C10—Fe1—C1—C2−113.1 (2)C20—Fe2—C23—C19−38.4 (2)
C10—Fe1—C1—C5127.8 (2)C20—Fe2—C23—C2281.1 (2)
C10—Fe1—C1—C117.9 (3)C21—Fe2—C23—C19−82.1 (2)
C1—Fe1—C2—C3119.7 (3)C21—Fe2—C23—C2237.3 (2)
C3—Fe1—C2—C1−119.7 (3)C22—Fe2—C23—C19−119.4 (3)
C4—Fe1—C2—C1−82.0 (2)C24—Fe2—C23—C1973.1 (3)
C4—Fe1—C2—C337.7 (2)C24—Fe2—C23—C22−167.5 (2)
C5—Fe1—C2—C1−37.8 (2)C26—Fe2—C23—C19−169.0 (3)
C5—Fe1—C2—C381.9 (2)C26—Fe2—C23—C22−49.6 (4)
C6—Fe1—C2—C1129.6 (2)C27—Fe2—C23—C19157.0 (3)
C6—Fe1—C2—C3−110.7 (2)C27—Fe2—C23—C22−83.6 (3)
C7—Fe1—C2—C1171.6 (2)C28—Fe2—C23—C19114.2 (2)
C7—Fe1—C2—C3−68.7 (3)C28—Fe2—C23—C22−126.4 (2)
C9—Fe1—C2—C147.6 (4)C19—Fe2—C24—C25−127.3 (2)
C9—Fe1—C2—C3167.3 (3)C19—Fe2—C24—C28114.3 (3)
C10—Fe1—C2—C185.9 (2)C20—Fe2—C24—C25−84.1 (3)
C10—Fe1—C2—C3−154.4 (2)C20—Fe2—C24—C28157.5 (3)
C1—Fe1—C3—C2−37.3 (2)C21—Fe2—C24—C25−48.4 (5)
C1—Fe1—C3—C481.7 (3)C21—Fe2—C24—C28−166.8 (4)
C2—Fe1—C3—C4118.9 (3)C23—Fe2—C24—C25−168.1 (2)
C4—Fe1—C3—C2−118.9 (3)C23—Fe2—C24—C2873.5 (3)
C5—Fe1—C3—C2−81.1 (2)C25—Fe2—C24—C28−118.4 (4)
C5—Fe1—C3—C437.8 (2)C26—Fe2—C24—C2537.5 (2)
C6—Fe1—C3—C288.9 (2)C26—Fe2—C24—C28−80.9 (3)
C6—Fe1—C3—C4−152.2 (2)C27—Fe2—C24—C2581.0 (3)
C7—Fe1—C3—C2131.5 (2)C27—Fe2—C24—C28−37.4 (4)
C7—Fe1—C3—C4−109.5 (2)C28—Fe2—C24—C25118.4 (4)
C8—Fe1—C3—C2172.0 (2)C19—Fe2—C25—C2472.7 (3)
C8—Fe1—C3—C4−69.1 (3)C19—Fe2—C25—C26−167.8 (2)
C10—Fe1—C3—C254.3 (4)C20—Fe2—C25—C24114.3 (2)
C10—Fe1—C3—C4173.2 (3)C20—Fe2—C25—C26−126.2 (3)
C1—Fe1—C4—C3−81.7 (2)C21—Fe2—C25—C24157.3 (2)
C1—Fe1—C4—C537.7 (2)C21—Fe2—C25—C26−83.2 (3)
C2—Fe1—C4—C3−38.0 (2)C22—Fe2—C25—C24−167.9 (3)
C2—Fe1—C4—C581.4 (2)C22—Fe2—C25—C26−48.3 (4)
C3—Fe1—C4—C5119.4 (3)C24—Fe2—C25—C26119.5 (3)
C5—Fe1—C4—C3−119.4 (3)C26—Fe2—C25—C24−119.5 (3)
C6—Fe1—C4—C356.2 (4)C27—Fe2—C25—C24−82.0 (3)
C6—Fe1—C4—C5175.6 (3)C27—Fe2—C25—C2637.6 (3)
C7—Fe1—C4—C387.2 (3)C28—Fe2—C25—C24−38.3 (3)
C7—Fe1—C4—C5−153.4 (2)C28—Fe2—C25—C2681.3 (3)
C8—Fe1—C4—C3129.7 (2)C20—Fe2—C26—C2574.2 (3)
C8—Fe1—C4—C5−110.9 (2)C20—Fe2—C26—C27−166.7 (3)
C9—Fe1—C4—C3169.0 (2)C21—Fe2—C26—C25114.8 (3)
C9—Fe1—C4—C5−71.6 (3)C21—Fe2—C26—C27−126.1 (3)
C1—Fe1—C5—C4−119.1 (3)C22—Fe2—C26—C25157.2 (2)
C2—Fe1—C5—C137.6 (2)C22—Fe2—C26—C27−83.6 (3)
C2—Fe1—C5—C4−81.5 (2)C23—Fe2—C26—C25−168.2 (3)
C3—Fe1—C5—C181.7 (2)C23—Fe2—C26—C27−49.1 (5)
C3—Fe1—C5—C4−37.4 (2)C24—Fe2—C26—C25−37.1 (2)
C4—Fe1—C5—C1119.1 (3)C24—Fe2—C26—C2782.0 (3)
C7—Fe1—C5—C1170.6 (3)C25—Fe2—C26—C27119.1 (4)
C7—Fe1—C5—C451.5 (4)C27—Fe2—C26—C25−119.1 (4)
C8—Fe1—C5—C1−155.6 (2)C28—Fe2—C26—C25−81.1 (3)
C8—Fe1—C5—C485.3 (2)C28—Fe2—C26—C2738.0 (3)
C9—Fe1—C5—C1−113.1 (2)C19—Fe2—C27—C26−168.9 (3)
C9—Fe1—C5—C4127.8 (2)C19—Fe2—C27—C28−50.5 (5)
C10—Fe1—C5—C1−73.6 (3)C21—Fe2—C27—C2673.6 (3)
C10—Fe1—C5—C4167.3 (2)C21—Fe2—C27—C28−168.0 (3)
C1—Fe1—C6—C7169.5 (2)C22—Fe2—C27—C26114.1 (3)
C1—Fe1—C6—C10−70.2 (3)C22—Fe2—C27—C28−127.5 (3)
C2—Fe1—C6—C7127.9 (2)C23—Fe2—C27—C26156.9 (3)
C2—Fe1—C6—C10−111.7 (2)C23—Fe2—C27—C28−84.7 (3)
C3—Fe1—C6—C783.5 (3)C24—Fe2—C27—C26−80.8 (3)
C3—Fe1—C6—C10−156.1 (2)C24—Fe2—C27—C2837.6 (3)
C4—Fe1—C6—C745.5 (4)C25—Fe2—C27—C26−37.6 (3)
C4—Fe1—C6—C10165.8 (3)C25—Fe2—C27—C2880.8 (3)
C7—Fe1—C6—C10120.4 (3)C26—Fe2—C27—C28118.4 (4)
C8—Fe1—C6—C7−38.5 (2)C28—Fe2—C27—C26−118.4 (4)
C8—Fe1—C6—C1082.0 (2)C19—Fe2—C28—C24−84.2 (3)
C9—Fe1—C6—C7−82.2 (2)C19—Fe2—C28—C27156.4 (3)
C9—Fe1—C6—C1038.2 (2)C20—Fe2—C28—C24−49.4 (6)
C10—Fe1—C6—C7−120.4 (3)C20—Fe2—C28—C27−168.8 (4)
C2—Fe1—C7—C6−74.5 (3)C22—Fe2—C28—C24−168.4 (2)
C2—Fe1—C7—C8167.7 (2)C22—Fe2—C28—C2772.2 (4)
C3—Fe1—C7—C6−114.2 (2)C23—Fe2—C28—C24−127.0 (3)
C3—Fe1—C7—C8128.0 (2)C23—Fe2—C28—C27113.6 (3)
C4—Fe1—C7—C6−157.1 (2)C24—Fe2—C28—C27−119.4 (5)
C4—Fe1—C7—C885.1 (3)C25—Fe2—C28—C2437.7 (3)
C5—Fe1—C7—C6168.2 (3)C25—Fe2—C28—C27−81.7 (3)
C5—Fe1—C7—C850.3 (4)C26—Fe2—C28—C2481.5 (3)
C6—Fe1—C7—C8−117.9 (3)C26—Fe2—C28—C27−38.0 (3)
C8—Fe1—C7—C6117.9 (3)C27—Fe2—C28—C24119.4 (5)
C9—Fe1—C7—C680.8 (2)C11—N1—C12—C13−81.2 (4)
C9—Fe1—C7—C8−37.1 (2)C11—N1—C12—C17156.6 (3)
C10—Fe1—C7—C636.9 (2)C12—N1—C11—C1178.4 (3)
C10—Fe1—C7—C8−81.0 (2)C18—N2—C17—C12160.1 (3)
C1—Fe1—C8—C7173.5 (3)C18—N2—C17—C16−74.6 (4)
C1—Fe1—C8—C953.4 (4)C17—N2—C18—C19168.3 (3)
C3—Fe1—C8—C7−71.8 (3)C11—C1—C2—Fe1−122.8 (3)
C3—Fe1—C8—C9168.1 (2)C11—C1—C2—C3177.7 (3)
C4—Fe1—C8—C7−111.0 (2)C5—C1—C2—C3−0.5 (4)
C4—Fe1—C8—C9128.9 (2)C11—C1—C5—C4−178.3 (3)
C5—Fe1—C8—C7−153.9 (2)Fe1—C1—C11—N149.8 (4)
C5—Fe1—C8—C986.0 (3)C2—C1—C11—N1141.3 (3)
C6—Fe1—C8—C738.4 (2)C5—C1—C11—N1−40.8 (5)
C6—Fe1—C8—C9−81.8 (3)Fe1—C1—C5—C459.1 (2)
C7—Fe1—C8—C9−120.1 (3)Fe1—C1—C2—C3−59.4 (3)
C9—Fe1—C8—C7120.1 (3)C5—C1—C2—Fe158.9 (2)
C10—Fe1—C8—C782.0 (2)C2—C1—C5—C40.0 (4)
C10—Fe1—C8—C9−38.1 (2)C11—C1—C5—Fe1122.6 (3)
C1—Fe1—C9—C8−153.0 (2)C2—C1—C5—Fe1−59.1 (2)
C1—Fe1—C9—C1088.3 (2)C1—C2—C3—Fe159.5 (2)
C2—Fe1—C9—C8174.2 (3)C1—C2—C3—C40.9 (4)
C2—Fe1—C9—C1055.5 (4)Fe1—C2—C3—C4−58.6 (3)
C4—Fe1—C9—C8−69.8 (3)C2—C3—C4—C5−0.9 (4)
C4—Fe1—C9—C10171.5 (2)C2—C3—C4—Fe159.0 (3)
C5—Fe1—C9—C8−110.3 (2)Fe1—C3—C4—C5−59.9 (3)
C5—Fe1—C9—C10131.0 (2)Fe1—C4—C5—C1−59.7 (2)
C6—Fe1—C9—C881.0 (2)C3—C4—C5—C10.6 (4)
C6—Fe1—C9—C10−37.8 (2)C3—C4—C5—Fe160.3 (3)
C7—Fe1—C9—C837.2 (2)Fe1—C6—C10—C9−59.4 (3)
C7—Fe1—C9—C10−81.5 (2)C7—C6—C10—Fe158.3 (2)
C8—Fe1—C9—C10−118.7 (3)C7—C6—C10—C9−1.1 (4)
C10—Fe1—C9—C8118.7 (3)C10—C6—C7—C81.4 (4)
C1—Fe1—C10—C6131.2 (2)Fe1—C6—C7—C860.1 (3)
C1—Fe1—C10—C9−110.2 (2)C10—C6—C7—Fe1−58.7 (2)
C2—Fe1—C10—C687.8 (2)Fe1—C7—C8—C959.5 (3)
C2—Fe1—C10—C9−153.6 (2)C6—C7—C8—C9−1.2 (4)
C3—Fe1—C10—C650.2 (4)C6—C7—C8—Fe1−60.7 (2)
C3—Fe1—C10—C9168.8 (3)C7—C8—C9—Fe1−59.3 (3)
C5—Fe1—C10—C6172.8 (2)C7—C8—C9—C100.5 (4)
C5—Fe1—C10—C9−68.6 (3)Fe1—C8—C9—C1059.8 (3)
C6—Fe1—C10—C9118.6 (3)C8—C9—C10—Fe1−59.4 (3)
C7—Fe1—C10—C6−37.0 (2)Fe1—C9—C10—C659.8 (2)
C7—Fe1—C10—C981.6 (2)C8—C9—C10—C60.4 (4)
C8—Fe1—C10—C6−80.9 (2)N1—C12—C13—C14−174.5 (3)
C8—Fe1—C10—C937.8 (2)C17—C12—C13—C14−53.7 (5)
C9—Fe1—C10—C6−118.6 (3)N1—C12—C17—N2−59.7 (4)
C20—Fe2—C19—C18−121.8 (4)N1—C12—C17—C16173.0 (3)
C20—Fe2—C19—C23118.2 (3)C13—C12—C17—N2179.5 (3)
C21—Fe2—C19—C18−159.0 (4)C13—C12—C17—C1652.3 (5)
C21—Fe2—C19—C20−37.2 (2)C12—C13—C14—C1556.5 (5)
C21—Fe2—C19—C2381.0 (2)C13—C14—C15—C16−57.8 (6)
C22—Fe2—C19—C18157.6 (3)C14—C15—C16—C1757.7 (5)
C22—Fe2—C19—C20−80.6 (2)C15—C16—C17—N2−179.5 (3)
C22—Fe2—C19—C2337.6 (2)C15—C16—C17—C12−55.1 (5)
C23—Fe2—C19—C18120.0 (4)N2—C18—C19—Fe2179.3 (2)
C23—Fe2—C19—C20−118.2 (3)N2—C18—C19—C2087.8 (4)
C24—Fe2—C19—C18−7.2 (3)N2—C18—C19—C23−90.3 (4)
C24—Fe2—C19—C20114.6 (2)Fe2—C19—C20—C2159.1 (3)
C24—Fe2—C19—C23−127.2 (2)C18—C19—C20—Fe2122.0 (4)
C25—Fe2—C19—C18−47.5 (4)C18—C19—C20—C21−179.0 (3)
C25—Fe2—C19—C2074.3 (3)C23—C19—C20—Fe2−59.6 (2)
C25—Fe2—C19—C23−167.5 (2)C23—C19—C20—C21−0.6 (4)
C27—Fe2—C19—C1870.8 (5)Fe2—C19—C23—C22−59.2 (3)
C27—Fe2—C19—C20−167.4 (3)C18—C19—C23—Fe2−122.0 (4)
C27—Fe2—C19—C23−49.2 (4)C18—C19—C23—C22178.8 (3)
C28—Fe2—C19—C1835.8 (4)C20—C19—C23—Fe259.6 (2)
C28—Fe2—C19—C20157.6 (2)C20—C19—C23—C220.4 (4)
C28—Fe2—C19—C23−84.2 (3)Fe2—C20—C21—C2259.7 (3)
C19—Fe2—C20—C21−119.8 (3)C19—C20—C21—Fe2−59.2 (2)
C21—Fe2—C20—C19119.8 (3)C19—C20—C21—C220.5 (4)
C22—Fe2—C20—C1982.1 (2)Fe2—C21—C22—C2359.7 (3)
C22—Fe2—C20—C21−37.7 (2)C20—C21—C22—Fe2−59.9 (3)
C23—Fe2—C20—C1938.0 (2)C20—C21—C22—C23−0.3 (4)
C23—Fe2—C20—C21−81.7 (3)Fe2—C22—C23—C1959.7 (3)
C24—Fe2—C20—C19−84.1 (2)C21—C22—C23—Fe2−59.8 (3)
C24—Fe2—C20—C21156.2 (2)C21—C22—C23—C19−0.1 (4)
C25—Fe2—C20—C19−126.5 (2)Fe2—C24—C25—C26−59.3 (3)
C25—Fe2—C20—C21113.7 (2)C28—C24—C25—Fe260.4 (3)
C26—Fe2—C20—C19−167.6 (2)C28—C24—C25—C261.1 (5)
C26—Fe2—C20—C2172.6 (3)Fe2—C24—C28—C2759.6 (3)
C28—Fe2—C20—C19−49.4 (5)C25—C24—C28—Fe2−60.8 (3)
C28—Fe2—C20—C21−169.1 (4)C25—C24—C28—C27−1.2 (5)
C19—Fe2—C21—C2037.5 (2)Fe2—C25—C26—C27−59.5 (3)
C19—Fe2—C21—C22−81.3 (2)C24—C25—C26—Fe259.0 (3)
C20—Fe2—C21—C22−118.8 (3)C24—C25—C26—C27−0.5 (5)
C22—Fe2—C21—C20118.8 (3)Fe2—C26—C27—C28−59.9 (3)
C23—Fe2—C21—C2081.1 (2)C25—C26—C27—Fe259.7 (3)
C23—Fe2—C21—C22−37.7 (2)C25—C26—C27—C28−0.2 (5)
C24—Fe2—C21—C20−51.3 (5)Fe2—C27—C28—C24−59.2 (3)
C24—Fe2—C21—C22−170.1 (3)C26—C27—C28—Fe260.1 (3)
C25—Fe2—C21—C20−84.8 (3)C26—C27—C28—C240.9 (5)
C25—Fe2—C21—C22156.4 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1A···N20.902.362.848 (4)114

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2124).

References

  • Base, T., Cisarova, I. & Stepnicka, P. (2002). Inorg. Chem. Commun. 5, 46-50.
  • Beer, P. D. (1998). Acc. Chem. Res.31, 71–80.
  • Cho, D.-J., Jeon, S.-J., Kim, H.-S., Cho, C.-S., Shim, S.-C. & Kim, T.-J. (1999). Tetrahedron Asymmetry, 10, 3833–3848.
  • Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  • Hess, A., Brosch, O., Weyhermuller, T. & Metzler-Nolte, N. (1999). J. Organomet. Chem.589, 75–84.
  • Rigaku (2005). CrystalClear Rigaku Corporation, Tokyo, Japan.
  • Roberto, D., Ugo, R., Bruni, S., Cariati, E., Cariati, F., Fantucci, P., Invernizzi, I., Quici, S., Ledoux, I. & Zyss, J. (2000). Organometallics, 19, 1775–1788.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Sutcliffe, O. B., Bryce, M. R. & Batsanov, A. S. (2002). J. Organomet. Chem.656, 211–216.
  • Yang, J.-X., Tian, Y.-P., Liu, Q.-L., Xie, Y.-S., Fun, H.-K., Chantrapromma, S. & Razak, I. A. (2002). Acta Cryst. C58, m43–m44. [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography