PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2008 November 1; 64(Pt 11): m1423.
Published online 2008 October 18. doi:  10.1107/S1600536808032698
PMCID: PMC2959581

Penta­carbonyl-1κ2 C,2κ3 C-(ferrocenyl­diphenyl­phosphine-1κP)[μ-2-(4-methyl­phen­yl)-2-aza­propane-1,3-dithiol­ato-1:2κ4 S,S′:S,S′]diiron(I)(FeFe)

Abstract

The title compound, [Fe2(C9H11NS2){Fe(C5H5)(C17H14P)}(CO)5], was prepared as an aza­dithiol­ato–iron model for the iron-only hydrogenase active site. The Fe2S2 unit exhibits a butterfly conformation and the ferrocenyldiphenyl­phosphine ligand is trans to the Fe—Fe bond. The Fe—Fe distance of 2.5160 (8) Å is longer than found in related model structures. Intra­molecular C—H(...)S and inter­molecular C—H(...)O hydrogen bonds are observed.

Related literature

For general background, see: Cammack (1999 [triangle]); Evans & Pickett (2003 [triangle]); Nicolet et al. (1999 [triangle]); Peters et al. (1998 [triangle]). For related structures, see: Hou et al. (2006 [triangle]); Lawrence et al. (2001 [triangle]); Ott et al. (2004 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-m1423-scheme1.jpg

Experimental

Crystal data

  • [Fe3(C5H5)(C9H11NS2)(C17H14P)(CO)5]
  • M r = 819.25
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-m1423-efi1.jpg
  • a = 13.600 (2) Å
  • b = 10.8964 (19) Å
  • c = 23.396 (4) Å
  • β = 94.741 (3)°
  • V = 3455.2 (11) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 1.45 mm−1
  • T = 298 (2) K
  • 0.20 × 0.20 × 0.10 mm

Data collection

  • Bruker SMART APEX CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 1997 [triangle]) T min = 0.760, T max = 0.868
  • 21457 measured reflections
  • 8202 independent reflections
  • 4258 reflections with I > 2σ(I)
  • R int = 0.070

Refinement

  • R[F 2 > 2σ(F 2)] = 0.048
  • wR(F 2) = 0.079
  • S = 0.80
  • 8202 reflections
  • 434 parameters
  • H-atom parameters constrained
  • Δρmax = 0.66 e Å−3
  • Δρmin = −0.39 e Å−3

Data collection: SMART (Bruker, 1997 [triangle]); cell refinement: SAINT-Plus (Bruker, 2001 [triangle]); data reduction: SAINT-Plus; 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: SHELXL97.

Table 1
Selected bond lengths (Å)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808032698/ci2685sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808032698/ci2685Isup2.hkl

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

Acknowledgments

The authors thank the Science Foundation of Nantong Municipality (grant No. K2007011), the Science Foundation of Nantong University (grant Nos. 06Z017 and 06Z022) and the National Natural Science Foundation of China (grant No. 20276009) for financial support.

supplementary crystallographic information

Comment

The iron-only hydrogenases are enzymes that can efficiently catalyze the reversible reaction of hydrogen production (Cammack, 1999; Evans & Pickett, 2003). The active site at which this reaction takes place is composed of a butterfly shaped Fe2S2 unit covalently linked to a conventional Fe4S4 cluster by a bridged cysteinyl thioether (Peters et al., 1998; Nicolet et al., 1999). We have prepared the title complex as a structural model for the iron-only hydrogenases active site. Herein we report its crystal structure.

The molecular structure of the title complex is shown in Fig.1 and selected bond distances are listed in Table 1. In the Fe2S2 unit, the Fe—Fe distance of 2.5160 (8) Å is slightly longer than those observed in related complexes (Lawrence et al., 2001; Ott et al., 2004). The FcPPh2 (Fc is ferrocenyl and Ph is phenyl) ligand is in apical position (trans to Fe—Fe bond), with an Fe—P distance of 2.2565 (10) Å. The Fe1—C([equivalent]O) distances are ~0.04 Å shorter than those found in a related complex (Hou et al., 2006), consistent with an increase in the charge of Fe1 because one of the CO ligands was replaced by the FcPPh2 ligand. The ferrocene unit is covalently linked to the Fe2S2 unit via the bridged diphenyl P atom, with an Fe1—P1—C23 angle of 118.32 (12)°. The N1 atom is displaced from the C5/C8/C9 plane by 0.168 (3) Å, and the sum of angles around N1 is 355.8°.

Intramolecular C—H···S and intermolecular C—H···O hydrogen bonds are observed.

Experimental

The starting material [Fe2(µ-SCH2)2(4-CH3C6H4N)(CO)6] was obtained in 50% yield according to the literature method (Hou et al., 2006). The solution of Me3NO (120 mg, 1.06 mmol) was added to a red solution of [Fe2(µ-SCH2)2(4-CH3C6H4N)(CO)6] (0.50 g, 1.05 mmol) with FcPPh2 (0.39 g, 1.05 mmol) in CH3CN (100 ml) via syringe under a nitrogen atmosphere. The reaction mixture was stirred at ambient temperature until the TLC indicated there was no remaining carbonyl complex of starting material. The solvent was removed under vacuum and the resulted dark red residue was purified by column chromatography on silica gel eluting with CH2Cl2-hexane (1:5 v/v). A dark red solid was obtained from recrystallization in n-pentane-CH2Cl2. Single crystals of the title compound for X-ray analysis were grown from a CH2Cl2-hexane (1:5 v/v) solution by slow evaporation at ambient temperature.

Refinement

H atoms were placed in geometrically calculated positions (C—H = 0.93–0.98 Å) and refined as riding, with Uiso(H) = 1.2Ueq(C) and 1.5Ueq(Cmethyl)

Figures

Fig. 1.
The molecular structure of the title complex, with displacement ellipsoids drawn at the 30% probability level.

Crystal data

[Fe3(C5H5)(C9H11NS2)(C17H14P)(CO)5]F(000) = 1672
Mr = 819.25Dx = 1.575 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2549 reflections
a = 13.600 (2) Åθ = 2.4–22.0°
b = 10.8964 (19) ŵ = 1.45 mm1
c = 23.396 (4) ÅT = 298 K
β = 94.741 (3)°Block, red
V = 3455.2 (11) Å30.20 × 0.20 × 0.10 mm
Z = 4

Data collection

Bruker SMART APEX CCD area-detector diffractometer8202 independent reflections
Radiation source: fine-focus sealed tube4258 reflections with I > 2σ(I)
graphiteRint = 0.070
[var phi] and ω scansθmax = 28.4°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 1997)h = −17→18
Tmin = 0.760, Tmax = 0.868k = −9→14
21457 measured reflectionsl = −31→30

Refinement

Refinement on F20 restraints
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.048w = 1/[σ2(Fo2) + (0.0157P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.079(Δ/σ)max = 0.001
S = 0.80Δρmax = 0.66 e Å3
8202 reflectionsΔρmin = −0.38 e Å3
434 parameters

Special details

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 F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > σ(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ 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
Fe10.20737 (4)0.18453 (5)0.30929 (2)0.03252 (14)
Fe20.20176 (4)0.09491 (5)0.40808 (2)0.03988 (16)
Fe30.08083 (4)0.09519 (5)0.11522 (2)0.04244 (16)
S10.34466 (7)0.12772 (9)0.36528 (4)0.0387 (2)
S20.15575 (7)−0.00994 (9)0.32718 (4)0.0382 (2)
P10.26239 (7)0.19707 (9)0.22109 (4)0.0316 (2)
O10.2115 (2)−0.1033 (3)0.49363 (13)0.0791 (11)
O20.2652 (3)0.3021 (3)0.48103 (14)0.1006 (13)
O3−0.0037 (2)0.1481 (3)0.42412 (14)0.0962 (12)
O40.2502 (2)0.4345 (2)0.34576 (12)0.0634 (9)
O50.0021 (2)0.2479 (3)0.27912 (12)0.0661 (9)
N10.3407 (2)−0.1259 (3)0.34951 (12)0.0409 (8)
C10.4517 (4)−0.3802 (4)0.56016 (18)0.0874 (16)
H1A0.4496−0.46710.55350.131*
H1B0.4066−0.35920.58810.131*
H1C0.5173−0.35660.57410.131*
C20.4224 (3)−0.3132 (4)0.50438 (17)0.0536 (11)
C30.3533 (3)−0.3595 (4)0.46376 (18)0.0529 (11)
H30.3241−0.43480.47060.063*
C40.3255 (3)−0.2992 (4)0.41345 (16)0.0459 (10)
H40.2792−0.33460.38700.055*
C50.3662 (3)−0.1853 (4)0.40172 (16)0.0394 (9)
C60.4364 (3)−0.1384 (4)0.44210 (17)0.0485 (11)
H60.4658−0.06340.43530.058*
C70.4635 (3)−0.2009 (4)0.49226 (17)0.0579 (12)
H70.5107−0.16670.51860.069*
C80.2455 (3)−0.1362 (3)0.31877 (16)0.0479 (11)
H8A0.2156−0.21210.33040.057*
H8B0.2551−0.14360.27830.057*
C90.3917 (3)−0.0175 (3)0.33541 (15)0.0448 (10)
H9A0.3883−0.01030.29400.054*
H9B0.4606−0.02660.34900.054*
C100.2131 (3)−0.0291 (4)0.45986 (18)0.0539 (12)
C110.2391 (3)0.2194 (4)0.45270 (18)0.0651 (14)
C120.0758 (3)0.1262 (4)0.41723 (17)0.0561 (12)
C130.2339 (3)0.3362 (4)0.32971 (15)0.0385 (10)
C140.0838 (3)0.2218 (3)0.28947 (16)0.0431 (10)
C150.0207 (4)0.2515 (5)0.0789 (2)0.0749 (15)
H150.05680.31960.06300.090*
C16−0.0165 (4)0.1463 (5)0.0488 (2)0.0738 (15)
H16−0.01010.12870.00810.089*
C17−0.0633 (3)0.0727 (5)0.0861 (2)0.0736 (15)
H17−0.0958−0.00580.07660.088*
C18−0.0557 (3)0.1293 (5)0.1406 (2)0.0686 (14)
H18−0.08260.09790.17540.082*
C19−0.0044 (3)0.2407 (4)0.1355 (2)0.0662 (14)
H190.01150.29990.16640.079*
C200.1400 (3)−0.0774 (4)0.12177 (17)0.0518 (11)
H200.1039−0.15460.11520.062*
C210.1848 (3)−0.0097 (4)0.08032 (18)0.0551 (12)
H210.1854−0.03120.03970.066*
C220.2278 (3)0.0960 (4)0.10657 (15)0.0440 (10)
H220.26380.15980.08740.053*
C230.2103 (2)0.0944 (3)0.16603 (14)0.0331 (9)
C240.1549 (3)−0.0139 (3)0.17502 (16)0.0429 (10)
H240.1310−0.04010.21150.051*
C250.3951 (2)0.1685 (3)0.22119 (14)0.0303 (8)
C260.4591 (3)0.2380 (3)0.25719 (15)0.0380 (9)
H260.43380.29980.27910.046*
C270.5593 (3)0.2175 (4)0.26120 (16)0.0471 (11)
H270.60110.26500.28570.056*
C280.5975 (3)0.1257 (4)0.22858 (17)0.0483 (11)
H280.66500.11030.23150.058*
C290.5357 (3)0.0582 (3)0.19212 (16)0.0455 (11)
H290.5618−0.00150.16930.055*
C300.4351 (3)0.0770 (3)0.18864 (15)0.0370 (9)
H300.39370.02830.16450.044*
C310.2548 (3)0.3488 (3)0.18691 (15)0.0343 (9)
C320.3189 (3)0.3814 (3)0.14616 (16)0.0477 (11)
H320.36770.32660.13710.057*
C330.3115 (3)0.4942 (4)0.11883 (17)0.0577 (12)
H330.35440.51410.09130.069*
C340.2412 (3)0.5761 (4)0.13229 (18)0.0591 (12)
H340.23640.65190.11400.071*
C350.1777 (3)0.5472 (4)0.17249 (18)0.0547 (12)
H350.13010.60340.18170.066*
C360.1843 (3)0.4339 (3)0.19954 (15)0.0427 (10)
H360.14050.41480.22670.051*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Fe10.0317 (3)0.0340 (3)0.0323 (3)−0.0013 (3)0.0052 (2)−0.0022 (2)
Fe20.0415 (4)0.0483 (4)0.0305 (3)−0.0029 (3)0.0065 (3)−0.0030 (3)
Fe30.0349 (3)0.0523 (4)0.0393 (3)0.0000 (3)−0.0020 (3)−0.0046 (3)
S10.0357 (6)0.0427 (6)0.0374 (6)−0.0044 (5)0.0019 (5)0.0000 (5)
S20.0405 (6)0.0395 (6)0.0343 (6)−0.0058 (5)0.0014 (5)0.0002 (4)
P10.0296 (5)0.0336 (6)0.0319 (6)0.0006 (5)0.0038 (4)−0.0019 (4)
O10.103 (3)0.087 (3)0.051 (2)0.012 (2)0.0248 (19)0.0228 (18)
O20.138 (3)0.099 (3)0.067 (3)−0.033 (3)0.026 (2)−0.042 (2)
O30.055 (2)0.151 (4)0.084 (3)0.020 (2)0.018 (2)−0.018 (2)
O40.067 (2)0.046 (2)0.079 (2)−0.0107 (16)0.0131 (17)−0.0186 (16)
O50.0356 (18)0.080 (2)0.083 (2)0.0090 (16)0.0092 (17)0.0150 (17)
N10.049 (2)0.038 (2)0.036 (2)0.0013 (16)0.0032 (17)0.0055 (15)
C10.098 (4)0.094 (4)0.067 (4)−0.003 (3)−0.013 (3)0.034 (3)
C20.056 (3)0.057 (3)0.047 (3)0.001 (2)0.002 (2)0.018 (2)
C30.055 (3)0.047 (3)0.058 (3)−0.009 (2)0.010 (2)0.012 (2)
C40.049 (3)0.044 (3)0.043 (3)−0.006 (2)−0.002 (2)−0.001 (2)
C50.041 (2)0.040 (3)0.037 (2)0.004 (2)0.0059 (19)0.0015 (19)
C60.042 (3)0.049 (3)0.054 (3)−0.007 (2)−0.001 (2)0.014 (2)
C70.050 (3)0.062 (3)0.059 (3)−0.004 (2)−0.011 (2)0.008 (2)
C80.063 (3)0.035 (3)0.044 (3)0.001 (2)−0.006 (2)−0.0051 (19)
C90.044 (2)0.046 (3)0.046 (3)0.012 (2)0.014 (2)0.009 (2)
C100.045 (3)0.080 (4)0.039 (3)0.002 (2)0.016 (2)−0.006 (2)
C110.072 (3)0.083 (4)0.043 (3)−0.010 (3)0.022 (3)−0.013 (3)
C120.056 (3)0.074 (3)0.039 (3)0.002 (3)0.005 (2)−0.006 (2)
C130.032 (2)0.044 (3)0.040 (2)0.004 (2)0.0056 (18)−0.004 (2)
C140.045 (3)0.037 (3)0.050 (3)−0.006 (2)0.012 (2)0.0042 (19)
C150.073 (4)0.067 (4)0.082 (4)0.013 (3)−0.011 (3)0.016 (3)
C160.065 (4)0.094 (5)0.058 (3)0.017 (3)−0.021 (3)−0.009 (3)
C170.038 (3)0.087 (4)0.093 (4)−0.001 (3)−0.016 (3)−0.020 (3)
C180.035 (3)0.098 (4)0.073 (4)0.004 (3)0.005 (2)−0.013 (3)
C190.045 (3)0.071 (4)0.080 (4)0.020 (3)−0.012 (3)−0.021 (3)
C200.055 (3)0.042 (3)0.056 (3)−0.001 (2)−0.011 (2)−0.013 (2)
C210.047 (3)0.076 (3)0.042 (3)0.003 (2)0.002 (2)−0.024 (2)
C220.038 (2)0.058 (3)0.036 (2)−0.005 (2)0.0070 (19)−0.006 (2)
C230.030 (2)0.037 (2)0.032 (2)0.0003 (18)0.0013 (17)−0.0005 (18)
C240.046 (3)0.045 (3)0.036 (2)−0.002 (2)−0.001 (2)−0.0014 (19)
C250.030 (2)0.032 (2)0.030 (2)0.0019 (17)0.0070 (17)0.0068 (16)
C260.037 (2)0.036 (2)0.042 (2)−0.0003 (19)0.010 (2)−0.0054 (18)
C270.036 (2)0.052 (3)0.052 (3)−0.010 (2)−0.003 (2)0.001 (2)
C280.025 (2)0.059 (3)0.061 (3)0.006 (2)0.004 (2)0.009 (2)
C290.039 (3)0.046 (3)0.053 (3)0.012 (2)0.015 (2)0.000 (2)
C300.037 (2)0.036 (2)0.038 (2)0.0036 (18)0.0033 (18)0.0005 (18)
C310.032 (2)0.035 (2)0.036 (2)0.0001 (17)0.0041 (18)0.0048 (17)
C320.042 (3)0.049 (3)0.053 (3)0.013 (2)0.007 (2)0.014 (2)
C330.053 (3)0.065 (3)0.057 (3)0.006 (3)0.014 (2)0.027 (2)
C340.060 (3)0.050 (3)0.067 (3)0.008 (2)−0.001 (3)0.023 (2)
C350.054 (3)0.045 (3)0.065 (3)0.021 (2)0.004 (2)0.009 (2)
C360.036 (2)0.050 (3)0.043 (2)0.008 (2)0.0061 (19)0.001 (2)

Geometric parameters (Å, °)

Fe1—C131.750 (4)C7—H70.93
Fe1—C141.754 (4)C8—H8A0.97
Fe1—P12.2565 (10)C8—H8B0.97
Fe1—S12.2762 (11)C9—H9A0.97
Fe1—S22.2818 (11)C9—H9B0.97
Fe1—Fe22.5160 (8)C15—C191.399 (5)
Fe2—C111.761 (5)C15—C161.417 (6)
Fe2—C121.777 (5)C15—H150.98
Fe2—C101.813 (5)C16—C171.379 (6)
Fe2—S22.2546 (11)C16—H160.98
Fe2—S12.2867 (11)C17—C181.413 (6)
Fe3—C222.025 (4)C17—H170.98
Fe3—C182.030 (4)C18—C191.410 (5)
Fe3—C162.034 (4)C18—H180.98
Fe3—C172.036 (4)C19—H190.98
Fe3—C242.038 (4)C20—C211.398 (5)
Fe3—C212.040 (4)C20—C241.425 (5)
Fe3—C232.041 (3)C20—H200.98
Fe3—C192.043 (4)C21—C221.409 (5)
Fe3—C152.044 (4)C21—H210.98
Fe3—C202.047 (4)C22—C231.431 (4)
S1—C91.864 (3)C22—H220.98
S2—C81.860 (4)C23—C241.425 (4)
P1—C231.806 (3)C24—H240.98
P1—C251.832 (3)C25—C261.385 (4)
P1—C311.836 (3)C25—C301.392 (4)
O1—C101.132 (4)C26—C271.376 (5)
O2—C111.157 (4)C26—H260.93
O3—C121.132 (4)C27—C281.385 (5)
O4—C131.151 (4)C27—H270.93
O5—C141.153 (4)C28—C291.363 (5)
N1—C51.400 (4)C28—H280.93
N1—C91.421 (4)C29—C301.380 (5)
N1—C81.433 (4)C29—H290.93
C1—C21.519 (5)C30—H300.93
C1—H1A0.96C31—C361.382 (4)
C1—H1B0.96C31—C321.391 (4)
C1—H1C0.96C32—C331.386 (5)
C2—C31.376 (5)C32—H320.93
C2—C71.385 (5)C33—C341.363 (5)
C3—C41.374 (5)C33—H330.93
C3—H30.93C34—C351.364 (5)
C4—C51.396 (5)C34—H340.93
C4—H40.93C35—C361.386 (4)
C5—C61.384 (5)C35—H350.93
C6—C71.381 (5)C36—H360.93
C6—H60.93
C13—Fe1—C1491.41 (17)N1—C8—S2117.6 (2)
C13—Fe1—P196.67 (12)N1—C8—H8A107.9
C14—Fe1—P197.31 (12)S2—C8—H8A107.9
C13—Fe1—S187.66 (12)N1—C8—H8B107.9
C14—Fe1—S1159.67 (12)S2—C8—H8B107.9
P1—Fe1—S1102.97 (4)H8A—C8—H8B107.2
C13—Fe1—S2152.46 (12)N1—C9—S1115.4 (2)
C14—Fe1—S287.77 (12)N1—C9—H9A108.4
P1—Fe1—S2110.75 (4)S1—C9—H9A108.4
S1—Fe1—S283.80 (4)N1—C9—H9B108.4
C13—Fe1—Fe297.87 (12)S1—C9—H9B108.4
C14—Fe1—Fe2103.39 (12)H9A—C9—H9B107.5
P1—Fe1—Fe2154.30 (4)O1—C10—Fe2173.4 (4)
S1—Fe1—Fe256.73 (3)O2—C11—Fe2178.3 (4)
S2—Fe1—Fe255.80 (3)O3—C12—Fe2178.3 (4)
C11—Fe2—C1290.8 (2)O4—C13—Fe1176.7 (3)
C11—Fe2—C10100.0 (2)O5—C14—Fe1176.7 (4)
C12—Fe2—C1095.26 (18)C19—C15—C16107.3 (5)
C11—Fe2—S2159.16 (15)C19—C15—Fe369.9 (3)
C12—Fe2—S289.71 (14)C16—C15—Fe369.3 (3)
C10—Fe2—S2100.70 (14)C19—C15—H15126.3
C11—Fe2—S185.74 (13)C16—C15—H15126.4
C12—Fe2—S1152.32 (14)Fe3—C15—H15126.4
C10—Fe2—S1112.39 (13)C17—C16—C15108.7 (5)
S2—Fe2—S184.18 (4)C17—C16—Fe370.3 (3)
C11—Fe2—Fe1102.51 (14)C15—C16—Fe370.0 (3)
C12—Fe2—Fe197.99 (13)C17—C16—H16125.6
C10—Fe2—Fe1153.62 (13)C15—C16—H16125.7
S2—Fe2—Fe156.83 (3)Fe3—C16—H16125.6
S1—Fe2—Fe156.34 (3)C16—C17—C18108.3 (5)
C22—Fe3—C18164.24 (18)C16—C17—Fe370.1 (3)
C22—Fe3—C16120.53 (19)C18—C17—Fe369.5 (2)
C18—Fe3—C1667.69 (19)C16—C17—H17126.0
C22—Fe3—C17153.86 (18)C18—C17—H17125.7
C18—Fe3—C1740.67 (16)Fe3—C17—H17125.8
C16—Fe3—C1739.61 (17)C19—C18—C17107.4 (4)
C22—Fe3—C2468.59 (15)C19—C18—Fe370.2 (2)
C18—Fe3—C24108.54 (17)C17—C18—Fe369.9 (2)
C16—Fe3—C24159.7 (2)C19—C18—H18126.3
C17—Fe3—C24124.54 (19)C17—C18—H18126.3
C22—Fe3—C2140.55 (13)Fe3—C18—H18126.3
C18—Fe3—C21154.22 (19)C15—C19—C18108.4 (4)
C16—Fe3—C21106.06 (18)C15—C19—Fe370.0 (2)
C17—Fe3—C21118.59 (18)C18—C19—Fe369.3 (2)
C24—Fe3—C2168.17 (16)C15—C19—H19125.9
C22—Fe3—C2341.20 (12)C18—C19—H19125.8
C18—Fe3—C23126.57 (17)Fe3—C19—H19126.0
C16—Fe3—C23157.2 (2)C21—C20—C24108.1 (4)
C17—Fe3—C23162.63 (19)C21—C20—Fe369.8 (2)
C24—Fe3—C2340.89 (12)C24—C20—Fe369.3 (2)
C21—Fe3—C2368.77 (14)C21—C20—H20125.8
C22—Fe3—C19127.14 (18)C24—C20—H20126.0
C18—Fe3—C1940.50 (15)Fe3—C20—H20126.1
C16—Fe3—C1967.59 (18)C20—C21—C22108.5 (4)
C17—Fe3—C1967.78 (18)C20—C21—Fe370.2 (2)
C24—Fe3—C19123.45 (18)C22—C21—Fe369.1 (2)
C21—Fe3—C19162.4 (2)C20—C21—H21125.9
C23—Fe3—C19110.29 (16)C22—C21—H21125.6
C22—Fe3—C15108.63 (18)Fe3—C21—H21125.7
C18—Fe3—C1567.97 (19)C21—C22—C23108.5 (3)
C16—Fe3—C1540.67 (16)C21—C22—Fe370.3 (2)
C17—Fe3—C1567.7 (2)C23—C22—Fe370.00 (19)
C24—Fe3—C15158.38 (19)C21—C22—H22125.9
C21—Fe3—C15124.6 (2)C23—C22—H22125.6
C23—Fe3—C15122.80 (18)Fe3—C22—H22125.7
C19—Fe3—C1540.03 (16)C24—C23—C22106.6 (3)
C22—Fe3—C2068.06 (16)C24—C23—P1126.1 (3)
C18—Fe3—C20120.63 (19)C22—C23—P1126.8 (3)
C16—Fe3—C20122.40 (18)C24—C23—Fe369.4 (2)
C17—Fe3—C20106.01 (18)C22—C23—Fe368.8 (2)
C24—Fe3—C2040.84 (13)P1—C23—Fe3132.96 (18)
C21—Fe3—C2040.00 (14)C23—C24—C20108.2 (3)
C23—Fe3—C2068.76 (14)C23—C24—Fe369.7 (2)
C19—Fe3—C20157.4 (2)C20—C24—Fe369.9 (2)
C15—Fe3—C20159.8 (2)C23—C24—H24125.9
C9—S1—Fe1107.79 (13)C20—C24—H24125.9
C9—S1—Fe2111.20 (12)Fe3—C24—H24125.9
Fe1—S1—Fe266.93 (3)C26—C25—C30118.0 (3)
C8—S2—Fe2108.94 (12)C26—C25—P1118.5 (3)
C8—S2—Fe1116.93 (13)C30—C25—P1123.4 (3)
Fe2—S2—Fe167.37 (3)C27—C26—C25121.5 (3)
C23—P1—C25102.96 (16)C27—C26—H26119.3
C23—P1—C31104.03 (16)C25—C26—H26119.3
C25—P1—C31100.01 (15)C26—C27—C28119.6 (4)
C23—P1—Fe1118.32 (12)C26—C27—H27120.2
C25—P1—Fe1112.95 (11)C28—C27—H27120.2
C31—P1—Fe1116.22 (12)C29—C28—C27119.7 (4)
C5—N1—C9119.7 (3)C29—C28—H28120.2
C5—N1—C8123.4 (3)C27—C28—H28120.2
C9—N1—C8112.7 (3)C28—C29—C30120.9 (4)
C2—C1—H1A109.5C28—C29—H29119.5
C2—C1—H1B109.5C30—C29—H29119.5
H1A—C1—H1B109.5C29—C30—C25120.3 (4)
C2—C1—H1C109.5C29—C30—H30119.9
H1A—C1—H1C109.5C25—C30—H30119.9
H1B—C1—H1C109.5C36—C31—C32117.4 (3)
C3—C2—C7116.6 (4)C36—C31—P1121.7 (3)
C3—C2—C1122.2 (4)C32—C31—P1120.8 (3)
C7—C2—C1121.2 (4)C33—C32—C31121.1 (4)
C4—C3—C2122.7 (4)C33—C32—H32119.4
C4—C3—H3118.7C31—C32—H32119.4
C2—C3—H3118.7C34—C33—C32120.0 (4)
C3—C4—C5120.6 (4)C34—C33—H33120.0
C3—C4—H4119.7C32—C33—H33120.0
C5—C4—H4119.7C33—C34—C35120.3 (4)
C6—C5—C4117.1 (4)C33—C34—H34119.9
C6—C5—N1122.2 (4)C35—C34—H34119.9
C4—C5—N1120.6 (4)C34—C35—C36120.0 (4)
C7—C6—C5121.3 (4)C34—C35—H35120.0
C7—C6—H6119.4C36—C35—H35120.0
C5—C6—H6119.4C31—C36—C35121.3 (4)
C6—C7—C2121.7 (4)C31—C36—H36119.4
C6—C7—H7119.1C35—C36—H36119.4
C2—C7—H7119.1
C13—Fe1—Fe2—C11−5.79 (19)C20—Fe3—C18—C17−78.6 (3)
C14—Fe1—Fe2—C11−99.1 (2)C16—C15—C19—C180.7 (5)
P1—Fe1—Fe2—C11118.10 (17)Fe3—C15—C19—C18−58.8 (3)
S1—Fe1—Fe2—C1176.16 (16)C16—C15—C19—Fe359.5 (3)
S2—Fe1—Fe2—C11−177.00 (16)C17—C18—C19—C15−1.0 (5)
C13—Fe1—Fe2—C1286.84 (18)Fe3—C18—C19—C1559.3 (3)
C14—Fe1—Fe2—C12−6.51 (19)C17—C18—C19—Fe3−60.3 (3)
P1—Fe1—Fe2—C12−149.28 (16)C22—Fe3—C19—C1573.8 (3)
S1—Fe1—Fe2—C12168.78 (14)C18—Fe3—C19—C15−119.7 (4)
S2—Fe1—Fe2—C12−84.38 (14)C16—Fe3—C19—C15−38.3 (3)
C13—Fe1—Fe2—C10−153.7 (3)C17—Fe3—C19—C15−81.3 (3)
C14—Fe1—Fe2—C10112.9 (3)C24—Fe3—C19—C15161.0 (3)
P1—Fe1—Fe2—C10−29.8 (3)C21—Fe3—C19—C1533.6 (7)
S1—Fe1—Fe2—C10−71.8 (3)C23—Fe3—C19—C15117.2 (3)
S2—Fe1—Fe2—C1035.1 (3)C20—Fe3—C19—C15−159.5 (4)
C13—Fe1—Fe2—S2171.21 (12)C22—Fe3—C19—C18−166.5 (3)
C14—Fe1—Fe2—S277.86 (13)C16—Fe3—C19—C1881.4 (3)
P1—Fe1—Fe2—S2−64.90 (8)C17—Fe3—C19—C1838.4 (3)
S1—Fe1—Fe2—S2−106.84 (4)C24—Fe3—C19—C18−79.2 (3)
C13—Fe1—Fe2—S1−81.95 (12)C21—Fe3—C19—C18153.3 (5)
C14—Fe1—Fe2—S1−175.30 (13)C23—Fe3—C19—C18−123.0 (3)
P1—Fe1—Fe2—S141.94 (8)C15—Fe3—C19—C18119.7 (4)
S2—Fe1—Fe2—S1106.84 (4)C20—Fe3—C19—C18−39.7 (6)
C13—Fe1—S1—C9−152.98 (16)C22—Fe3—C20—C21−37.4 (2)
C14—Fe1—S1—C9119.3 (4)C18—Fe3—C20—C21157.3 (3)
P1—Fe1—S1—C9−56.67 (12)C16—Fe3—C20—C2175.7 (3)
S2—Fe1—S1—C953.25 (12)C17—Fe3—C20—C21115.6 (3)
Fe2—Fe1—S1—C9106.02 (12)C24—Fe3—C20—C21−119.6 (3)
C13—Fe1—S1—Fe2101.00 (11)C23—Fe3—C20—C21−81.9 (2)
C14—Fe1—S1—Fe213.3 (4)C19—Fe3—C20—C21−173.9 (4)
P1—Fe1—S1—Fe2−162.70 (4)C15—Fe3—C20—C2147.0 (6)
S2—Fe1—S1—Fe2−52.78 (3)C22—Fe3—C20—C2482.2 (2)
C11—Fe2—S1—C9150.9 (2)C18—Fe3—C20—C24−83.1 (3)
C12—Fe2—S1—C9−125.5 (3)C16—Fe3—C20—C24−164.7 (3)
C10—Fe2—S1—C951.8 (2)C17—Fe3—C20—C24−124.8 (3)
S2—Fe2—S1—C9−47.37 (13)C21—Fe3—C20—C24119.6 (3)
Fe1—Fe2—S1—C9−101.01 (13)C23—Fe3—C20—C2437.7 (2)
C11—Fe2—S1—Fe1−108.09 (16)C19—Fe3—C20—C24−54.3 (5)
C12—Fe2—S1—Fe1−24.5 (3)C15—Fe3—C20—C24166.6 (5)
C10—Fe2—S1—Fe1152.84 (15)C24—C20—C21—C22−0.1 (5)
S2—Fe2—S1—Fe153.64 (3)Fe3—C20—C21—C2258.7 (3)
C11—Fe2—S2—C8120.3 (4)C24—C20—C21—Fe3−58.8 (3)
C12—Fe2—S2—C8−148.17 (19)C22—Fe3—C21—C20119.9 (4)
C10—Fe2—S2—C8−52.87 (18)C18—Fe3—C21—C20−49.8 (5)
S1—Fe2—S2—C858.87 (13)C16—Fe3—C21—C20−121.6 (3)
Fe1—Fe2—S2—C8112.07 (13)C17—Fe3—C21—C20−80.8 (3)
C11—Fe2—S2—Fe18.2 (4)C24—Fe3—C21—C2037.8 (2)
C12—Fe2—S2—Fe199.76 (14)C23—Fe3—C21—C2081.9 (2)
C10—Fe2—S2—Fe1−164.94 (13)C19—Fe3—C21—C20172.2 (5)
S1—Fe2—S2—Fe1−53.20 (3)C15—Fe3—C21—C20−162.2 (3)
C13—Fe1—S2—C8−119.6 (3)C18—Fe3—C21—C22−169.7 (4)
C14—Fe1—S2—C8151.61 (18)C16—Fe3—C21—C22118.5 (3)
P1—Fe1—S2—C854.64 (14)C17—Fe3—C21—C22159.3 (3)
S1—Fe1—S2—C8−46.91 (14)C24—Fe3—C21—C22−82.1 (3)
Fe2—Fe1—S2—C8−100.52 (14)C23—Fe3—C21—C22−38.0 (2)
C13—Fe1—S2—Fe2−19.1 (3)C19—Fe3—C21—C2252.3 (7)
C14—Fe1—S2—Fe2−107.87 (12)C15—Fe3—C21—C2277.9 (3)
P1—Fe1—S2—Fe2155.17 (4)C20—Fe3—C21—C22−119.9 (4)
S1—Fe1—S2—Fe253.61 (3)C20—C21—C22—C230.4 (5)
C13—Fe1—P1—C23−153.80 (18)Fe3—C21—C22—C2359.8 (3)
C14—Fe1—P1—C23−61.51 (18)C20—C21—C22—Fe3−59.4 (3)
S1—Fe1—P1—C23117.07 (13)C18—Fe3—C22—C21163.4 (6)
S2—Fe1—P1—C2328.86 (14)C16—Fe3—C22—C21−78.7 (3)
Fe2—Fe1—P1—C2382.08 (15)C17—Fe3—C22—C21−44.7 (5)
C13—Fe1—P1—C2585.87 (17)C24—Fe3—C22—C2181.0 (3)
C14—Fe1—P1—C25178.16 (17)C23—Fe3—C22—C21119.3 (3)
S1—Fe1—P1—C25−3.25 (13)C19—Fe3—C22—C21−162.5 (3)
S2—Fe1—P1—C25−91.46 (13)C15—Fe3—C22—C21−121.8 (3)
Fe2—Fe1—P1—C25−38.24 (16)C20—Fe3—C22—C2136.9 (2)
C13—Fe1—P1—C31−28.89 (18)C18—Fe3—C22—C2344.1 (7)
C14—Fe1—P1—C3163.40 (18)C16—Fe3—C22—C23162.0 (2)
S1—Fe1—P1—C31−118.01 (13)C17—Fe3—C22—C23−164.0 (4)
S2—Fe1—P1—C31153.78 (13)C24—Fe3—C22—C23−38.3 (2)
Fe2—Fe1—P1—C31−153.00 (13)C21—Fe3—C22—C23−119.3 (3)
C7—C2—C3—C40.1 (6)C19—Fe3—C22—C2378.2 (3)
C1—C2—C3—C4179.4 (4)C15—Fe3—C22—C23118.9 (3)
C2—C3—C4—C5−0.9 (6)C20—Fe3—C22—C23−82.4 (2)
C3—C4—C5—C61.4 (5)C21—C22—C23—C24−0.6 (4)
C3—C4—C5—N1177.6 (3)Fe3—C22—C23—C2459.4 (2)
C9—N1—C5—C63.7 (5)C21—C22—C23—P1171.5 (3)
C8—N1—C5—C6−151.7 (3)Fe3—C22—C23—P1−128.5 (3)
C9—N1—C5—C4−172.3 (3)C21—C22—C23—Fe3−60.0 (3)
C8—N1—C5—C432.3 (5)C25—P1—C23—C24109.2 (3)
C4—C5—C6—C7−1.1 (6)C31—P1—C23—C24−146.8 (3)
N1—C5—C6—C7−177.2 (3)Fe1—P1—C23—C24−16.1 (4)
C5—C6—C7—C20.3 (6)C25—P1—C23—C22−61.3 (3)
C3—C2—C7—C60.2 (6)C31—P1—C23—C2242.6 (4)
C1—C2—C7—C6−179.0 (4)Fe1—P1—C23—C22173.3 (3)
C5—N1—C8—S298.7 (4)C25—P1—C23—Fe3−155.9 (2)
C9—N1—C8—S2−58.1 (4)C31—P1—C23—Fe3−51.9 (3)
Fe2—S2—C8—N1−20.0 (3)Fe1—P1—C23—Fe378.7 (3)
Fe1—S2—C8—N153.6 (3)C22—Fe3—C23—C24−118.2 (3)
C5—N1—C9—S1−84.2 (4)C18—Fe3—C23—C2475.4 (3)
C8—N1—C9—S173.6 (3)C16—Fe3—C23—C24−161.7 (4)
Fe1—S1—C9—N1−79.0 (3)C17—Fe3—C23—C2437.8 (6)
Fe2—S1—C9—N1−7.5 (3)C21—Fe3—C23—C24−80.8 (2)
C22—Fe3—C15—C19−126.1 (3)C19—Fe3—C23—C24118.1 (2)
C18—Fe3—C15—C1937.5 (3)C15—Fe3—C23—C24161.0 (2)
C16—Fe3—C15—C19118.4 (4)C20—Fe3—C23—C24−37.7 (2)
C17—Fe3—C15—C1981.6 (3)C18—Fe3—C23—C22−166.4 (3)
C24—Fe3—C15—C19−47.4 (6)C16—Fe3—C23—C22−43.4 (5)
C21—Fe3—C15—C19−168.2 (3)C17—Fe3—C23—C22156.0 (5)
C23—Fe3—C15—C19−82.8 (3)C24—Fe3—C23—C22118.2 (3)
C20—Fe3—C15—C19157.0 (5)C21—Fe3—C23—C2237.5 (2)
C22—Fe3—C15—C16115.5 (3)C19—Fe3—C23—C22−123.7 (3)
C18—Fe3—C15—C16−80.9 (3)C15—Fe3—C23—C22−80.8 (3)
C17—Fe3—C15—C16−36.9 (3)C20—Fe3—C23—C2280.5 (2)
C24—Fe3—C15—C16−165.8 (4)C22—Fe3—C23—P1121.1 (4)
C21—Fe3—C15—C1673.3 (4)C18—Fe3—C23—P1−45.3 (4)
C23—Fe3—C15—C16158.8 (3)C16—Fe3—C23—P177.7 (5)
C19—Fe3—C15—C16−118.4 (4)C17—Fe3—C23—P1−82.9 (6)
C20—Fe3—C15—C1638.6 (7)C24—Fe3—C23—P1−120.7 (3)
C19—C15—C16—C17−0.1 (5)C21—Fe3—C23—P1158.6 (3)
Fe3—C15—C16—C1759.8 (3)C19—Fe3—C23—P1−2.6 (3)
C19—C15—C16—Fe3−59.9 (3)C15—Fe3—C23—P140.3 (3)
C22—Fe3—C16—C17157.2 (3)C20—Fe3—C23—P1−158.4 (3)
C18—Fe3—C16—C17−37.8 (3)C22—C23—C24—C200.5 (4)
C24—Fe3—C16—C1745.4 (6)P1—C23—C24—C20−171.6 (3)
C21—Fe3—C16—C17115.7 (3)Fe3—C23—C24—C2059.5 (3)
C23—Fe3—C16—C17−171.0 (3)C22—C23—C24—Fe3−59.0 (2)
C19—Fe3—C16—C17−81.8 (3)P1—C23—C24—Fe3128.9 (3)
C15—Fe3—C16—C17−119.5 (4)C21—C20—C24—C23−0.2 (4)
C20—Fe3—C16—C1775.3 (4)Fe3—C20—C24—C23−59.4 (3)
C22—Fe3—C16—C15−83.3 (3)C21—C20—C24—Fe359.1 (3)
C18—Fe3—C16—C1581.7 (3)C22—Fe3—C24—C2338.56 (19)
C17—Fe3—C16—C15119.5 (4)C18—Fe3—C24—C23−124.9 (2)
C24—Fe3—C16—C15164.9 (4)C16—Fe3—C24—C23159.4 (5)
C21—Fe3—C16—C15−124.8 (3)C17—Fe3—C24—C23−167.2 (2)
C23—Fe3—C16—C15−51.5 (6)C21—Fe3—C24—C2382.3 (2)
C19—Fe3—C16—C1537.7 (3)C19—Fe3—C24—C23−82.6 (3)
C20—Fe3—C16—C15−165.2 (3)C15—Fe3—C24—C23−48.1 (5)
C15—C16—C17—C18−0.6 (5)C20—Fe3—C24—C23119.3 (3)
Fe3—C16—C17—C1859.1 (3)C22—Fe3—C24—C20−80.8 (2)
C15—C16—C17—Fe3−59.7 (3)C18—Fe3—C24—C20115.7 (3)
C22—Fe3—C17—C16−49.2 (6)C16—Fe3—C24—C2040.1 (6)
C18—Fe3—C17—C16119.5 (5)C17—Fe3—C24—C2073.5 (3)
C24—Fe3—C17—C16−162.6 (3)C21—Fe3—C24—C20−37.0 (2)
C21—Fe3—C17—C16−80.5 (4)C23—Fe3—C24—C20−119.3 (3)
C23—Fe3—C17—C16168.3 (5)C19—Fe3—C24—C20158.0 (3)
C19—Fe3—C17—C1681.2 (3)C15—Fe3—C24—C20−167.4 (5)
C15—Fe3—C17—C1637.8 (3)C23—P1—C25—C26176.8 (3)
C20—Fe3—C17—C16−121.8 (3)C31—P1—C25—C2669.7 (3)
C22—Fe3—C17—C18−168.7 (4)Fe1—P1—C25—C26−54.5 (3)
C16—Fe3—C17—C18−119.5 (5)C23—P1—C25—C30−6.0 (3)
C24—Fe3—C17—C1877.9 (3)C31—P1—C25—C30−113.1 (3)
C21—Fe3—C17—C18160.0 (3)Fe1—P1—C25—C30122.8 (3)
C23—Fe3—C17—C1848.8 (7)C30—C25—C26—C27−0.3 (5)
C19—Fe3—C17—C18−38.3 (3)P1—C25—C26—C27177.1 (3)
C15—Fe3—C17—C18−81.7 (3)C25—C26—C27—C280.1 (6)
C20—Fe3—C17—C18118.6 (3)C26—C27—C28—C291.2 (6)
C16—C17—C18—C191.0 (5)C27—C28—C29—C30−2.2 (6)
Fe3—C17—C18—C1960.5 (3)C28—C29—C30—C252.1 (6)
C16—C17—C18—Fe3−59.6 (3)C26—C25—C30—C29−0.8 (5)
C22—Fe3—C18—C1943.4 (8)P1—C25—C30—C29−178.0 (3)
C16—Fe3—C18—C19−81.1 (3)C23—P1—C31—C36104.2 (3)
C17—Fe3—C18—C19−118.0 (4)C25—P1—C31—C36−149.6 (3)
C24—Fe3—C18—C19120.2 (3)Fe1—P1—C31—C36−27.7 (3)
C21—Fe3—C18—C19−161.8 (4)C23—P1—C31—C32−74.4 (3)
C23—Fe3—C18—C1978.3 (3)C25—P1—C31—C3231.8 (3)
C15—Fe3—C18—C19−37.1 (3)Fe1—P1—C31—C32153.6 (3)
C20—Fe3—C18—C19163.4 (3)C36—C31—C32—C33−0.8 (6)
C22—Fe3—C18—C17161.4 (6)P1—C31—C32—C33177.8 (3)
C16—Fe3—C18—C1736.9 (3)C31—C32—C33—C340.9 (6)
C24—Fe3—C18—C17−121.8 (3)C32—C33—C34—C35−0.2 (7)
C21—Fe3—C18—C17−43.8 (6)C33—C34—C35—C36−0.4 (7)
C23—Fe3—C18—C17−163.8 (3)C32—C31—C36—C350.2 (6)
C19—Fe3—C18—C17118.0 (4)P1—C31—C36—C35−178.5 (3)
C15—Fe3—C18—C1780.9 (3)C34—C35—C36—C310.4 (6)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C22—H22···O2i0.982.533.224 (5)128
C24—H24···S20.982.723.561 (4)144

Symmetry codes: (i) x, −y+1/2, z−1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2685).

References

  • Bruker (1997). SMART and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Bruker (2001). SAINT-Plus Bruker AXS Inc., Madison, Wisconsin, USA.
  • Cammack, R. (1999). Nature (London), 297, 214–215. [PubMed]
  • Evans, D. J. & Pickett, C. J. (2003). Chem. Soc. Rev.32, 268–275. [PubMed]
  • Hou, J., Peng, X. J., Liu, J. F., Gao, Y. L., Zhao, X., Gao, S. & Han, K. L. (2006). Eur. J. Inorg. Chem. pp. 4679–4686.
  • Lawrence, J. D., Li, H., Rauchfuss, T. B., Bénard, M. & Rohmer, M.-M. (2001). Angew. Chem. Int. Ed.113, 1818–1821.
  • Nicolet, Y., Piras, C., Legrand, P. C., Hatchikian, E. & Fontecilla-Camps, J. C. (1999). Structure, 7, 13–23. [PubMed]
  • Ott, S., Borgström, M., Kritikos, M., Lomoth, R., Bergquist, J., Åkermark, B., Hammarström, L. & Sun, L. (2004). Inorg. Chem.43, 4683–4692. [PubMed]
  • Peters, J. W., Lanzilotta, W. N., Lemon, B. J. & Seefeldt, L. C. (1998). Science, 282, 1853–1858. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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