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In the adduct ferrocene-1,1'-diyl­bis­(di­phenyl­methanol)-1,2-bis(4-pyridyl)­ethene (1/1), [Fe(C18H15O)2]·C12H10N2, there is an intramolecular O-H...O hydrogen bond in the ferro­cene­diol component and a single O-H...N hydrogen bond linking the diol to the di­amine, which is disordered over two sets of sites, so forming a finite monomeric adduct. In the adduct ferrocene-1,1'-diyl­bis­(di­phenyl­methanol)-1,6-di­amino­hexane (2/1), 2[Fe(C18H15O)2]·C6H16N2, the amine lies across a centre of inversion in space group P\overline 1. There is an intramolecular O-H...O hydrogen bond in the ferrocenediol, and the molecular components are linked by O-H...N and N-H...O hydrogen bonds, one of each type, into a C_3^3(13)[R_6^6(12)] chain of rings.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270101017152/sk1515sup1.cif
Contains datablocks global, I, II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270101017152/sk1515Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270101017152/sk1515IIsup3.hkl
Contains datablock II

CCDC references: 180123; 180124

Comment top

The organometallic diol ferrocene-1,1'-diylbis(diphenylmethanol), [Fe(C5H4CPh2OH)2], forms a 1: 1 hydrogen-bonded adduct with 4,4'-bipyridyl in which only half of the bipyridyl molecules are involved in the supramolecular aggregation; this takes the form of a finite centrosymmetric three-component aggregate diol–diamine–diol, while the remainder of the bipyridyl molecules occupy isolated sites within the structure (Glidewell et al., 1994). By contrast, the 1:1 adduct formed by this diol with 1,2-bis(4-pyridyl)ethane crystallizes as a finite monomeric adduct in which one of the N atoms plays no part in the hydrogen bonding (Zakaria et al., 2001). The 1:1 adduct formed by the ferrocenediol with 1,2-diaminoethane, by contrast, exhibits a much more complex structure, in the form of two independent four-molecule aggregates, (diol)2.(diamine)2, both of which are centrosymmetric, but which exhibit different patterns of hydrogen bonds (Zakaria et al., 2001). Continuing this theme, we have now synthesized and structurally characterized two further adducts with related diamines, the 1:1 adduct with trans-1,2-bis(4-pyridyl)ethene, [Fe(C18H15O)2]·C12H10N2, (I), and the 2:1 adduct with 1,6-diaminohexane, 2[Fe(C18H15O)2]·C6H16N2, (II).

Compound (I) consists of finite 1:1 aggregates (Fig. 1); in addition to an intermolecular O—H···O hydrogen bond within the diol (Table 2), there is an O—H···N hydrogen bond linking the molecular components. By contrast with the fully ordered diamine in the analogous 1,2-bis(4-pyridyl)ethane adduct, in (I), the 1,2-bis(4-pyridyl)ethene molecules exhibit orientational disorder over two sets of sites, of a type previously observed in the 1:1 adduct of this diamine with 4,4'-sulfonyldiphenol (Ferguson et al., 1999). The two sets of sites, whose refined site-occupation factors are 0.601 (5) and 0.399 (5), can be most simply envisaged as resulting from a 180° rotation about a line which approximates to the N···N vector, so that the heteroaromatic ring position are similar in the two orientations, but the two central CC bonds are nearly orthogonal. In neither orientation of the diamine does the remote N act as a hydrogen-bond acceptor.

In compound (II), the 1,6-diaminohexane component lies across a centre of inversion in space group P1, selected for the sake of convenience as that at (1/2, 1/2, 1/2), while the ferrocenediol lies in a general position. There is the usual intramolecular O—H···O hydrogen bond within the ferrocenediol, and the free hydroxyl group forms an O—H···N hydrogen bond with the amine (Table 4); a centrosymmetric three-molecule diol–diamine–diol aggregate thus results. In addition, the amino N1 atom at (x, y, z), which is a component of the three-molecule aggregate centred at (1/2, 1/2, 1/2), acts as a hydrogen-bond donor, via H1A, to O1 at (2 - x, 1 - y, 1 - z), which is a component of the aggregate centred at (1.5, 1/2, 1/2); N1 at (2 - x, 1 - y, 1 - z), in turn, acts as donor to O1 at (x, y, z), producing a centrosymmetric R66(12) ring centred at (1, 1/2, 1/2). The symmetry-related N1 atom in the aggregate centred at (1/2, 1/2, 1/2) is at (1 - x, 1 - y, 1 - z), and this acts as a hydrogen-bond donor to O1 at (-1 + x, y, z), part of the aggregate centred at (-0.5, 1/2, 1/2). Propagation of this N—H···O hydrogen bond thus generates a C33(13)[R66(12)] chain of rings running parallel to the [100] direction; in this chain, the R66(12) rings are centred at (n, 1/2, 1/2) (n = zero or integer), while the diamines linking the R66(12) rings are centred at (n + 1/2, 1/2, 1/2) (n = zero or integer) (Fig. 3). The second H atom of the amino group, H1B, plays no role in the hydrogen bonding.

The pairwise linking of the ferrocenediol molecules into centrosymmetric R66(12) rings by pairs of X—H units, which can act as both donors and acceptors of hydrogen bonds, observed here for X = N, has also been observed in the finite 1:1 adduct formed between the ferrocenediol and methanol, when X = O (Ferguson et al., 1993). The overall ribbon-like structure of (II) has the hydrogen-bonded rings along the centre of the ribbon, with the ferrocenyl and phenyl units on the periphery. This arrangement effectively precludes the formation of any hydrogen bonds, hard or soft, between adjacent chains, and thus possibly accounts for the non-participation in the hydrogen bonding of H1B. In much the same way, in the finite zero-dimensional aggregates formed in the adduct of the ferrocenediol with 1,2-diaminoethane, the polar hydrogen-bonded core of each aggregate is prevented by the lipophilic organic substituents from interaction with the polar cores of adjacent aggregates.

In compound (I), both components of the amine are significantly non-planar (Table 1), and in compound (II), the terminal N—C—C—C fragment of the amine does not adopt the trans-planar conformation observed for the C—C–C—-C fragments (Table 3). The bond lengths and angles show no unexpected features.

Experimental top

For each adduct, equimolar quantities of the ferrocenediol and the appropriate diamine were separately dissolved in methanol. The component solutions were mixed and the mixtures were set aside to crystallize, producing analytically pure (I) and (II). Analyses, compound (I): found C 78.7, H 5.3, N 3.7%; C48H40FeN2O2 requires C 78.7, H 5.5, N 3.8%; compound (II): found C 76.4, H 6.4, N 2.3%; C78H76Fe2N2O4 requires C 77.0, H 6.3, N 2.3%. Crystals suitable for single-crystal X-ray diffraction were selected directly from the analytical samples.

Refinement top

Compounds (I) and (II) both crystallize in the triclinic system; for each, space group P1 was assumed and subsequently confirmed by the analysis. In compound (I), the amine component is disordered over two sets of sites; the minor component was refined with a common isotropic displacement parameter for all the C and N atoms. All H atoms were treated as riding, with C—H = 0.95–0.99 Å, N—H = 0.91 Å and O—H = 0.84 Å.

Computing details top

For both compounds, data collection: KappaCCD Server Software (Nonius, 1997); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2001); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997) and PRPKAPPA (Ferguson, 1999).

Figures top
[Figure 1] Fig. 1. The molecular aggregate in (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. For the sake of clarity, only the major orientation of the diamine is shown.
[Figure 2] Fig. 2. The molecular components of (II), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 3] Fig. 3. Part of the crystal structure of (II) showing the formation of a C33(13)[R66(12)] chain of rings along [100]. For the sake of clarity, H atoms bonded to C atoms have been omitted. Atoms marked with an asterisk (*) or hash (#) are at the symmetry positions (2 - x, 1 - y, 1 - z) and (1 - x, 1 - y, 1 - z), respectively.
(I) Ferrocene-1,1'-diylbis(diphenylmethanol)–1,2-bis(4'-pyridyl)ethene (1/1) top
Crystal data top
[Fe(C18H15O)2]·C12H10N2Z = 2
Mr = 732.67F(000) = 768
Triclinic, P1Dx = 1.332 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.6393 (4) ÅCell parameters from 6061 reflections
b = 11.4219 (5) Åθ = 2.6–25.0°
c = 17.7338 (10) ŵ = 0.46 mm1
α = 76.7680 (18)°T = 150 K
β = 87.4580 (17)°Block, orange
γ = 74.064 (3)°0.23 × 0.16 × 0.14 mm
V = 1827.24 (15) Å3
Data collection top
KappaCCD
diffractometer
6460 independent reflections
Radiation source: fine-focus sealed X-ray tube4709 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.060
ϕ scans, and ω scans with κ offsetsθmax = 25.0°, θmin = 2.6°
Absorption correction: multi-scan
(DENZO-SMN; Otwinowski & Minor, 1997)
h = 011
Tmin = 0.902, Tmax = 0.939k = 1213
16969 measured reflectionsl = 2021
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.050H-atom parameters constrained
wR(F2) = 0.125 w = 1/[σ2(Fo2) + (0.0328P)2 + 1.2945P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
6460 reflectionsΔρmax = 0.55 e Å3
526 parametersΔρmin = 0.48 e Å3
64 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0044 (10)
Crystal data top
[Fe(C18H15O)2]·C12H10N2γ = 74.064 (3)°
Mr = 732.67V = 1827.24 (15) Å3
Triclinic, P1Z = 2
a = 9.6393 (4) ÅMo Kα radiation
b = 11.4219 (5) ŵ = 0.46 mm1
c = 17.7338 (10) ÅT = 150 K
α = 76.7680 (18)°0.23 × 0.16 × 0.14 mm
β = 87.4580 (17)°
Data collection top
KappaCCD
diffractometer
6460 independent reflections
Absorption correction: multi-scan
(DENZO-SMN; Otwinowski & Minor, 1997)
4709 reflections with I > 2σ(I)
Tmin = 0.902, Tmax = 0.939Rint = 0.060
16969 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.05064 restraints
wR(F2) = 0.125H-atom parameters constrained
S = 1.03Δρmax = 0.55 e Å3
6460 reflectionsΔρmin = 0.48 e Å3
526 parameters
Special details top

Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm] Fox, G·C. & Holmes, K·C. (1966). Acta Cryst. 20, 886–891] which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Fe10.58624 (4)0.72258 (4)0.81709 (2)0.02481 (15)
O10.5773 (2)0.4707 (2)0.73149 (12)0.0306 (5)
O20.3278 (2)0.66740 (19)0.69347 (11)0.0268 (5)
C10.7158 (3)0.4598 (3)0.76479 (18)0.0284 (7)
C110.6947 (3)0.5387 (3)0.82439 (17)0.0265 (7)
C120.5780 (3)0.5494 (3)0.87751 (17)0.0284 (7)
C130.5986 (3)0.6217 (3)0.92872 (18)0.0312 (7)
C140.7287 (3)0.6560 (3)0.90870 (17)0.0302 (7)
C150.7882 (3)0.6049 (3)0.84492 (17)0.0285 (7)
C20.2741 (3)0.7655 (3)0.73402 (16)0.0234 (6)
C210.4007 (3)0.8128 (3)0.75196 (17)0.0240 (7)
C220.4134 (3)0.8753 (3)0.81122 (18)0.0275 (7)
C230.5449 (3)0.9119 (3)0.80049 (19)0.0307 (7)
C240.6126 (3)0.8723 (3)0.73557 (18)0.0314 (7)
C250.5257 (3)0.8115 (3)0.70495 (17)0.0274 (7)
C310.7682 (3)0.3196 (3)0.80226 (19)0.0296 (7)
C320.7704 (3)0.2725 (3)0.8817 (2)0.0357 (8)
C330.7966 (3)0.1445 (3)0.9128 (2)0.0395 (8)
C340.8236 (3)0.0621 (3)0.8644 (2)0.0380 (8)
C350.8293 (3)0.1063 (3)0.7853 (2)0.0397 (8)
C360.8018 (3)0.2339 (3)0.7548 (2)0.0350 (8)
C410.8173 (3)0.4988 (3)0.70036 (18)0.0298 (7)
C420.7654 (3)0.5625 (3)0.62633 (19)0.0345 (8)
C430.8581 (4)0.5985 (3)0.5686 (2)0.0428 (9)
C441.0041 (4)0.5698 (3)0.5850 (2)0.0454 (9)
C451.0576 (4)0.5061 (3)0.6580 (2)0.0424 (9)
C460.9654 (3)0.4701 (3)0.7156 (2)0.0352 (8)
C510.1590 (3)0.8709 (3)0.68255 (16)0.0254 (7)
C520.1677 (3)0.9924 (3)0.66032 (19)0.0359 (8)
C530.0621 (4)1.0847 (3)0.6122 (2)0.0446 (9)
C540.0529 (3)1.0549 (3)0.58558 (19)0.0409 (9)
C550.0630 (3)0.9329 (3)0.60755 (18)0.0366 (8)
C560.0408 (3)0.8416 (3)0.65594 (17)0.0309 (7)
C610.2069 (3)0.7107 (3)0.80876 (16)0.0232 (6)
C620.2243 (3)0.5828 (3)0.83339 (17)0.0266 (7)
C630.1710 (3)0.5339 (3)0.90432 (18)0.0311 (7)
C640.0995 (3)0.6124 (3)0.95085 (18)0.0329 (8)
C650.0752 (3)0.7401 (3)0.92526 (17)0.0307 (7)
C660.1271 (3)0.7898 (3)0.85407 (17)0.0283 (7)
N710.3676 (7)0.7351 (6)0.53449 (17)0.0402 (16)0.601 (5)
C720.4124 (5)0.8394 (5)0.5108 (3)0.0446 (17)0.601 (5)
C730.4835 (6)0.8597 (5)0.4412 (2)0.0390 (16)0.601 (5)
C740.5088 (8)0.7760 (5)0.3929 (4)0.0359 (17)0.601 (5)
C750.4566 (7)0.6713 (6)0.4150 (3)0.0359 (16)0.601 (5)
C760.3889 (10)0.6565 (8)0.4861 (3)0.0307 (15)0.601 (5)
C770.5887 (5)0.8000 (4)0.31690 (19)0.0370 (15)0.601 (5)
N810.7652 (5)0.8689 (6)0.0404 (3)0.0402 (14)0.601 (5)
C820.6355 (6)0.8445 (7)0.0431 (3)0.0438 (19)0.601 (5)
C830.5804 (7)0.7959 (7)0.11334 (15)0.0354 (15)0.601 (5)
C840.6463 (4)0.7841 (6)0.1839 (2)0.0309 (14)0.601 (5)
C850.7778 (4)0.8131 (5)0.1786 (2)0.0251 (13)0.601 (5)
C860.8357 (6)0.8535 (7)0.10747 (18)0.0359 (15)0.601 (5)
C870.5802 (4)0.7417 (4)0.26059 (15)0.0331 (14)0.601 (5)
N71A0.4009 (11)0.7434 (11)0.5397 (2)0.0297 (10)*0.399 (5)
C72A0.4710 (8)0.8256 (8)0.5011 (4)0.0297 (10)*0.399 (5)
C73A0.5226 (10)0.8304 (9)0.4264 (4)0.0297 (10)*0.399 (5)
C74A0.4971 (15)0.7452 (12)0.3876 (8)0.0297 (10)*0.399 (5)
C75A0.4243 (14)0.6614 (14)0.4280 (6)0.0297 (10)*0.399 (5)
C76A0.3781 (19)0.6581 (15)0.5036 (6)0.0297 (10)*0.399 (5)
C77A0.5395 (7)0.7481 (7)0.3036 (3)0.0297 (10)*0.399 (5)
N81A0.7340 (10)0.8570 (10)0.0263 (6)0.0297 (10)*0.399 (5)
C82A0.6172 (12)0.8216 (10)0.0569 (5)0.0297 (10)*0.399 (5)
C83A0.5900 (13)0.7940 (12)0.1357 (4)0.0297 (10)*0.399 (5)
C84A0.6884 (9)0.8008 (12)0.1884 (6)0.0297 (10)*0.399 (5)
C85A0.8115 (10)0.8345 (11)0.1590 (4)0.0297 (10)*0.399 (5)
C86A0.8251 (12)0.8656 (12)0.0791 (4)0.0297 (10)*0.399 (5)
C87A0.6540 (7)0.7869 (7)0.2746 (3)0.0297 (10)*0.399 (5)
H10.52480.54420.72700.046*
H20.33420.69870.64620.040*
H120.49960.51370.87820.034*
H130.53650.64360.96940.037*
H140.76880.70470.93370.036*
H150.87540.61320.82000.034*
H220.34610.89010.85110.033*
H230.57990.95530.83180.037*
H240.70190.88430.71540.038*
H250.54670.77600.66090.033*
H320.75370.32830.91560.043*
H330.79600.11400.96730.047*
H340.83820.02480.88550.046*
H350.85200.04970.75200.048*
H360.80590.26360.70040.042*
H420.66520.58180.61480.041*
H430.82120.64260.51820.051*
H441.06760.59420.54580.055*
H451.15800.48660.66910.051*
H461.00330.42560.76570.042*
H520.24701.01380.67800.043*
H530.06961.16800.59790.054*
H540.12461.11720.55250.049*
H550.14200.91180.58920.044*
H560.03180.75870.67110.037*
H620.27310.52840.80160.032*
H630.18380.44630.92080.037*
H640.06710.57871.00030.039*
H650.02280.79430.95640.037*
H660.10830.87780.83630.034*
H720.39530.89930.54190.053*0.601 (5)
H730.51570.93300.42610.047*0.601 (5)
H750.46660.61300.38320.043*0.601 (5)
H760.35450.58440.50200.037*0.601 (5)
H770.64560.85750.30950.044*0.601 (5)
H820.58150.86070.00340.053*0.601 (5)
H830.49490.76980.11320.042*0.601 (5)
H850.82930.80520.22480.030*0.601 (5)
H860.92690.87080.10600.043*0.601 (5)
H870.53440.67610.26850.040*0.601 (5)
H72A0.48640.88510.52720.036*0.399 (5)
H73A0.57320.88950.40270.036*0.399 (5)
H75A0.40490.60290.40240.036*0.399 (5)
H76A0.33150.59720.52940.036*0.399 (5)
H77A0.48370.72210.27110.036*0.399 (5)
H82A0.54880.81510.02220.036*0.399 (5)
H83A0.50490.77060.15340.036*0.399 (5)
H85A0.88450.83620.19270.036*0.399 (5)
H86A0.90550.89560.06000.036*0.399 (5)
H87A0.71480.80600.30810.036*0.399 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.0211 (2)0.0260 (3)0.0252 (3)0.00347 (17)0.00008 (17)0.00507 (19)
O10.0255 (11)0.0264 (12)0.0386 (13)0.0024 (9)0.0046 (9)0.0096 (11)
O20.0272 (11)0.0287 (12)0.0231 (11)0.0050 (9)0.0031 (9)0.0067 (9)
C10.0222 (15)0.0264 (17)0.0346 (18)0.0021 (12)0.0020 (13)0.0079 (14)
C110.0238 (15)0.0230 (17)0.0271 (16)0.0006 (12)0.0025 (12)0.0008 (13)
C120.0250 (16)0.0262 (17)0.0303 (17)0.0043 (13)0.0030 (13)0.0014 (14)
C130.0285 (17)0.0328 (19)0.0271 (17)0.0008 (14)0.0016 (13)0.0053 (15)
C140.0241 (16)0.0335 (19)0.0308 (18)0.0041 (13)0.0051 (13)0.0064 (15)
C150.0235 (15)0.0311 (18)0.0279 (17)0.0037 (13)0.0027 (13)0.0046 (14)
C20.0216 (14)0.0227 (16)0.0232 (16)0.0021 (12)0.0005 (12)0.0045 (13)
C210.0213 (15)0.0206 (16)0.0261 (16)0.0019 (12)0.0002 (12)0.0019 (13)
C220.0247 (15)0.0257 (17)0.0294 (17)0.0027 (13)0.0020 (13)0.0063 (14)
C230.0277 (16)0.0256 (18)0.0385 (19)0.0059 (13)0.0021 (14)0.0075 (15)
C240.0239 (16)0.0307 (18)0.0368 (19)0.0080 (13)0.0003 (14)0.0012 (15)
C250.0231 (15)0.0293 (18)0.0246 (16)0.0021 (13)0.0019 (12)0.0022 (14)
C310.0206 (15)0.0253 (17)0.0395 (19)0.0016 (12)0.0017 (13)0.0055 (15)
C320.0320 (17)0.0283 (19)0.043 (2)0.0001 (14)0.0064 (15)0.0086 (16)
C330.0340 (18)0.033 (2)0.043 (2)0.0027 (15)0.0057 (15)0.0017 (17)
C340.0259 (17)0.0259 (19)0.057 (2)0.0020 (14)0.0038 (15)0.0051 (17)
C350.0313 (18)0.031 (2)0.056 (2)0.0032 (14)0.0010 (16)0.0154 (18)
C360.0305 (17)0.0293 (19)0.042 (2)0.0041 (14)0.0019 (14)0.0066 (16)
C410.0306 (17)0.0243 (17)0.0344 (18)0.0029 (13)0.0020 (14)0.0123 (15)
C420.0352 (18)0.0335 (19)0.0367 (19)0.0061 (14)0.0036 (15)0.0160 (16)
C430.052 (2)0.042 (2)0.035 (2)0.0144 (17)0.0102 (16)0.0103 (17)
C440.049 (2)0.047 (2)0.045 (2)0.0171 (18)0.0199 (18)0.0214 (19)
C450.0318 (18)0.042 (2)0.057 (2)0.0089 (16)0.0106 (17)0.0226 (19)
C460.0309 (17)0.0333 (19)0.042 (2)0.0051 (14)0.0042 (15)0.0137 (16)
C510.0239 (15)0.0292 (18)0.0197 (15)0.0025 (13)0.0012 (12)0.0042 (13)
C520.0331 (18)0.033 (2)0.0383 (19)0.0090 (14)0.0051 (15)0.0010 (16)
C530.044 (2)0.032 (2)0.047 (2)0.0045 (16)0.0053 (17)0.0064 (17)
C540.0340 (19)0.046 (2)0.0294 (19)0.0043 (16)0.0034 (15)0.0009 (17)
C550.0273 (17)0.050 (2)0.0281 (18)0.0009 (15)0.0062 (13)0.0114 (16)
C560.0291 (16)0.0331 (19)0.0290 (17)0.0049 (14)0.0003 (13)0.0080 (15)
C610.0178 (14)0.0286 (17)0.0219 (15)0.0059 (12)0.0016 (12)0.0032 (13)
C620.0217 (15)0.0303 (18)0.0261 (16)0.0060 (13)0.0012 (12)0.0036 (14)
C630.0240 (15)0.0338 (19)0.0318 (18)0.0104 (14)0.0026 (13)0.0036 (15)
C640.0234 (16)0.047 (2)0.0248 (17)0.0096 (14)0.0013 (13)0.0007 (16)
C650.0210 (15)0.040 (2)0.0257 (17)0.0027 (13)0.0026 (12)0.0051 (15)
C660.0232 (15)0.0296 (18)0.0283 (17)0.0034 (13)0.0007 (13)0.0034 (14)
N710.046 (4)0.037 (3)0.036 (3)0.009 (3)0.007 (2)0.008 (2)
C720.035 (4)0.055 (4)0.037 (3)0.005 (3)0.001 (3)0.007 (3)
C730.046 (4)0.028 (4)0.045 (4)0.009 (3)0.001 (3)0.011 (3)
C740.038 (3)0.032 (5)0.034 (4)0.012 (3)0.006 (3)0.005 (3)
C750.032 (5)0.033 (4)0.039 (4)0.002 (3)0.001 (3)0.009 (3)
C760.037 (3)0.036 (3)0.018 (4)0.007 (3)0.003 (3)0.007 (3)
C770.035 (3)0.038 (4)0.040 (4)0.011 (3)0.002 (3)0.011 (3)
N810.032 (3)0.061 (4)0.032 (3)0.016 (3)0.002 (3)0.014 (3)
C820.044 (4)0.076 (6)0.028 (4)0.040 (4)0.023 (3)0.019 (4)
C830.031 (3)0.043 (4)0.028 (4)0.003 (3)0.005 (3)0.008 (4)
C840.020 (3)0.031 (4)0.039 (4)0.002 (3)0.008 (3)0.010 (3)
C850.014 (3)0.033 (3)0.019 (3)0.000 (2)0.008 (2)0.005 (2)
C860.034 (3)0.042 (4)0.024 (3)0.007 (3)0.001 (3)0.003 (4)
C870.030 (3)0.035 (3)0.034 (3)0.006 (2)0.010 (2)0.013 (3)
Geometric parameters (Å, º) top
Fe1—C242.038 (3)C54—C551.387 (5)
Fe1—C142.040 (3)C54—H540.95
Fe1—C132.040 (3)C55—C561.385 (4)
Fe1—C222.041 (3)C55—H550.95
Fe1—C232.041 (3)C56—H560.95
Fe1—C122.044 (3)C61—C621.390 (4)
Fe1—C252.044 (3)C61—C661.396 (4)
Fe1—C152.046 (3)C62—C631.392 (4)
Fe1—C112.050 (3)C62—H620.95
Fe1—C212.054 (3)C63—C641.382 (4)
O1—C11.447 (3)C63—H630.95
O1—H10.84C64—C651.381 (5)
O2—C21.435 (3)C64—H640.95
O2—H20.84C65—C661.392 (4)
C1—C111.512 (4)C65—H650.95
C1—C311.536 (4)C66—H660.95
C1—C411.539 (4)N71—C721.3492 (10)
C11—C151.431 (4)N71—C761.3496 (10)
C11—C121.432 (4)C72—C731.3882 (10)
C12—C131.413 (4)C72—H720.95
C12—H120.95C73—C741.3917 (10)
C13—C141.420 (4)C73—H730.95
C13—H130.95C74—C751.3911 (10)
C14—C151.417 (4)C74—C771.529 (5)
C14—H140.95C75—C761.3895 (10)
C15—H150.95C75—H750.95
C2—C611.528 (4)C76—H760.95
C2—C211.535 (4)C77—C871.3376 (10)
C2—C511.538 (4)C77—H770.95
C21—C221.426 (4)N81—C861.3493 (10)
C21—C251.433 (4)N81—C821.3497 (10)
C22—C231.431 (4)C82—C831.3887 (10)
C22—H220.95C82—H820.95
C23—C241.402 (4)C83—C841.3909 (10)
C23—H230.95C83—H830.95
C24—C251.419 (4)C84—C851.3899 (10)
C24—H240.95C84—C871.511 (4)
C25—H250.95C85—C861.3890 (10)
C31—C321.388 (4)C85—H850.95
C31—C361.396 (4)C86—H860.95
C32—C331.394 (5)C87—H870.95
C32—H320.95N71A—C72A1.3496 (10)
C33—C341.380 (5)N71A—C76A1.3498 (10)
C33—H330.95C72A—C73A1.3896 (10)
C34—C351.382 (5)C72A—H72A0.95
C34—H340.95C73A—C74A1.3907 (10)
C35—C361.387 (5)C73A—H73A0.95
C35—H350.95C74A—C75A1.3907 (10)
C36—H360.95C74A—C77A1.522 (10)
C41—C421.387 (4)C75A—C76A1.3896 (10)
C41—C461.398 (4)C75A—H75A0.95
C42—C431.395 (5)C76A—H76A0.95
C42—H420.95C77A—C87A1.3390 (10)
C43—C441.382 (5)C77A—H77A0.95
C43—H430.95N81A—C86A1.3493 (10)
C44—C451.376 (5)N81A—C82A1.3495 (10)
C44—H440.95C82A—C83A1.3896 (10)
C45—C461.389 (5)C82A—H82A0.95
C45—H450.95C83A—C84A1.3904 (10)
C46—H460.95C83A—H83A0.95
C51—C521.377 (4)C84A—C85A1.3900 (10)
C51—C561.401 (4)C84A—C87A1.531 (8)
C52—C531.397 (4)C85A—C86A1.3894 (10)
C52—H520.95C85A—H85A0.95
C53—C541.376 (5)C86A—H86A0.95
C53—H530.95C87A—H87A0.95
C1—O1—H1109.5C55—C56—H56119.9
C2—O2—H2109.5C51—C56—H56119.9
O1—C1—C11109.4 (2)C62—C61—C66118.8 (3)
O1—C1—C31102.4 (2)C62—C61—C2121.4 (3)
C11—C1—C31111.8 (2)C66—C61—C2119.7 (3)
O1—C1—C41109.9 (2)C61—C62—C63120.5 (3)
C11—C1—C41111.7 (2)C61—C62—H62119.7
C31—C1—C41111.3 (2)C63—C62—H62119.7
C15—C11—C12106.7 (3)C64—C63—C62120.1 (3)
C15—C11—C1129.0 (3)C64—C63—H63119.9
C12—C11—C1124.0 (3)C62—C63—H63119.9
C13—C12—C11108.7 (3)C65—C64—C63119.8 (3)
C13—C12—H12125.6C65—C64—H64120.1
C11—C12—H12125.6C63—C64—H64120.1
C12—C13—C14107.9 (3)C64—C65—C66120.3 (3)
C12—C13—H13126.0C64—C65—H65119.8
C14—C13—H13126.0C66—C65—H65119.8
C15—C14—C13108.1 (3)C65—C66—C61120.2 (3)
C15—C14—H14125.9C65—C66—H66119.9
C13—C14—H14125.9C61—C66—H66119.9
C14—C15—C11108.5 (3)C72—N71—C76117.0 (4)
C14—C15—H15125.8N71—C72—C73120.4 (5)
C11—C15—H15125.8N71—C72—H72119.8
O2—C2—C61107.6 (2)C73—C72—H72119.8
O2—C2—C21108.6 (2)C72—C73—C74122.0 (6)
C61—C2—C21110.8 (2)C72—C73—H73119.0
O2—C2—C51108.6 (2)C74—C73—H73119.0
C61—C2—C51110.2 (2)C75—C74—C73117.9 (7)
C21—C2—C51111.0 (2)C75—C74—C77121.1 (3)
C22—C21—C25106.8 (3)C73—C74—C77120.9 (3)
C22—C21—C2128.6 (3)C76—C75—C74116.6 (7)
C25—C21—C2124.3 (3)C76—C75—H75121.7
C21—C22—C23108.4 (3)C74—C75—H75121.7
C21—C22—H22125.8N71—C76—C75126.0 (7)
C23—C22—H22125.8N71—C76—H76117.0
C24—C23—C22107.8 (3)C75—C76—H76117.0
C24—C23—H23126.1C87—C77—C74121.4 (3)
C22—C23—H23126.1C87—C77—H77119.3
C23—C24—C25108.7 (3)C74—C77—H77119.3
C23—C24—H24125.7C86—N81—C82118.8 (6)
C25—C24—H24125.7N81—C82—C83120.7 (6)
C24—C25—C21108.2 (3)N81—C82—H82119.7
C24—C25—H25125.9C83—C82—H82119.7
C21—C25—H25125.9C82—C83—C84122.1 (6)
C32—C31—C36117.6 (3)C82—C83—H83119.0
C32—C31—C1122.9 (3)C84—C83—H83119.0
C36—C31—C1119.1 (3)C85—C84—C83115.1 (5)
C31—C32—C33121.1 (3)C85—C84—C87122.6 (3)
C31—C32—H32119.5C83—C84—C87122.3 (3)
C33—C32—H32119.5C86—C85—C84121.6 (5)
C34—C33—C32120.1 (3)C86—C85—H85119.2
C34—C33—H33119.9C84—C85—H85119.2
C32—C33—H33119.9N81—C86—C85121.4 (5)
C33—C34—C35119.8 (3)N81—C86—H86119.3
C33—C34—H34120.1C85—C86—H86119.3
C35—C34—H34120.1C77—C87—C84117.3 (3)
C34—C35—C36119.7 (3)C77—C87—H87121.3
C34—C35—H35120.2C84—C87—H87121.3
C36—C35—H35120.2C72A—N71A—C76A118.1 (7)
C35—C36—C31121.6 (3)N71A—C72A—C73A125.4 (8)
C35—C36—H36119.2N71A—C72A—H72A117.3
C31—C36—H36119.2C73A—C72A—H72A117.3
C42—C41—C46118.4 (3)C72A—C73A—C74A117.3 (11)
C42—C41—C1121.4 (3)C72A—C73A—H73A121.4
C46—C41—C1120.2 (3)C74A—C73A—H73A121.4
C41—C42—C43120.9 (3)C75A—C74A—C73A116.6 (14)
C41—C42—H42119.5C75A—C74A—C77A121.6 (7)
C43—C42—H42119.5C73A—C74A—C77A121.7 (7)
C44—C43—C42119.7 (3)C76A—C75A—C74A123.9 (16)
C44—C43—H43120.1C76A—C75A—H75A118.0
C42—C43—H43120.1C74A—C75A—H75A118.0
C45—C44—C43120.1 (3)N71A—C76A—C75A118.6 (13)
C45—C44—H44119.9N71A—C76A—H76A120.7
C43—C44—H44119.9C75A—C76A—H76A120.7
C44—C45—C46120.2 (3)C87A—C77A—C74A121.1 (5)
C44—C45—H45119.9C87A—C77A—H77A119.5
C46—C45—H45119.9C74A—C77A—H77A119.5
C45—C46—C41120.6 (3)C86A—N81A—C82A114.2 (12)
C45—C46—H46119.7N81A—C82A—C83A124.6 (12)
C41—C46—H46119.7N81A—C82A—H82A117.7
C52—C51—C56118.4 (3)C83A—C82A—H82A117.7
C52—C51—C2123.2 (3)C82A—C83A—C84A119.5 (12)
C56—C51—C2118.4 (3)C82A—C83A—H83A120.3
C51—C52—C53121.3 (3)C84A—C83A—H83A120.3
C51—C52—H52119.4C85A—C84A—C83A117.5 (11)
C53—C52—H52119.4C85A—C84A—C87A121.0 (5)
C54—C53—C52120.0 (3)C83A—C84A—C87A121.1 (6)
C54—C53—H53120.0C86A—C85A—C84A118.3 (10)
C52—C53—H53120.0C86A—C85A—H85A120.8
C53—C54—C55119.3 (3)C84A—C85A—H85A120.8
C53—C54—H54120.4N81A—C86A—C85A125.7 (11)
C55—C54—H54120.4N81A—C86A—H86A117.1
C56—C55—C54120.7 (3)C85A—C86A—H86A117.1
C56—C55—H55119.6C77A—C87A—C84A120.9 (5)
C54—C55—H55119.6C77A—C87A—H87A119.5
C55—C56—C51120.3 (3)C84A—C87A—H87A119.5
O1—C1—C11—C15147.2 (3)C51—C52—C53—C540.6 (5)
C31—C1—C11—C15100.1 (3)C52—C53—C54—C550.6 (5)
C41—C1—C11—C1525.3 (4)C53—C54—C55—C560.2 (5)
O1—C1—C11—C1239.6 (4)C54—C55—C56—C510.9 (5)
C31—C1—C11—C1273.1 (3)C52—C51—C56—C550.9 (4)
C41—C1—C11—C12161.5 (3)C2—C51—C56—C55178.0 (3)
C15—C11—C12—C130.7 (3)O2—C2—C61—C6210.1 (3)
C1—C11—C12—C13175.1 (3)C21—C2—C61—C62108.5 (3)
C11—C12—C13—C140.5 (3)C51—C2—C61—C62128.3 (3)
C12—C13—C14—C150.1 (3)O2—C2—C61—C66170.6 (2)
C13—C14—C15—C110.3 (3)C21—C2—C61—C6670.9 (3)
C12—C11—C15—C140.6 (3)C51—C2—C61—C6652.3 (3)
C1—C11—C15—C14174.7 (3)C66—C61—C62—C634.0 (4)
O2—C2—C21—C22156.5 (3)C2—C61—C62—C63175.4 (2)
C61—C2—C21—C2238.6 (4)C61—C62—C63—C640.3 (4)
C51—C2—C21—C2284.2 (4)C62—C63—C64—C652.9 (4)
O2—C2—C21—C2530.0 (4)C63—C64—C65—C662.4 (4)
C61—C2—C21—C25147.9 (3)C64—C65—C66—C611.4 (4)
C51—C2—C21—C2589.3 (3)C62—C61—C66—C654.5 (4)
C25—C21—C22—C230.0 (3)C2—C61—C66—C65174.9 (2)
C2—C21—C22—C23174.4 (3)C76—N71—C72—C733.1 (8)
C21—C22—C23—C240.1 (3)N71—C72—C73—C741.2 (8)
C22—C23—C24—C250.2 (3)C72—C73—C74—C752.0 (11)
C23—C24—C25—C210.1 (3)C72—C73—C74—C77179.4 (5)
C22—C21—C25—C240.1 (3)C73—C74—C75—C763.0 (12)
C2—C21—C25—C24174.8 (3)C77—C74—C75—C76178.3 (8)
O1—C1—C31—C32106.4 (3)C72—N71—C76—C752.0 (12)
C11—C1—C31—C3210.6 (4)C74—C75—C76—N711.1 (14)
C41—C1—C31—C32136.2 (3)C73—C74—C77—C87161.5 (6)
O1—C1—C31—C3667.0 (3)C75—C74—C77—C8717.1 (10)
C11—C1—C31—C36176.0 (2)C86—N81—C82—C834.6 (9)
C41—C1—C31—C3650.4 (3)N81—C82—C83—C847.8 (9)
C36—C31—C32—C333.8 (4)C82—C83—C84—C855.9 (9)
C1—C31—C32—C33169.7 (3)C82—C83—C84—C87174.7 (6)
C31—C32—C33—C341.2 (5)C83—C84—C85—C861.4 (10)
C32—C33—C34—C352.2 (5)C87—C84—C85—C86179.2 (6)
C33—C34—C35—C362.7 (5)C82—N81—C86—C850.2 (10)
C34—C35—C36—C310.0 (5)C84—C85—C86—N811.4 (11)
C32—C31—C36—C353.2 (4)C74—C77—C87—C84172.0 (5)
C1—C31—C36—C35170.6 (3)C83—C84—C87—C77139.5 (6)
O1—C1—C41—C4214.2 (4)C85—C84—C87—C7741.2 (8)
C11—C1—C41—C42107.4 (3)C76A—N71A—C72A—C73A0.0 (13)
C31—C1—C41—C42126.9 (3)N71A—C72A—C73A—C74A1.4 (13)
O1—C1—C41—C46165.7 (3)C72A—C73A—C74A—C75A1.1 (19)
C11—C1—C41—C4672.7 (4)C72A—C73A—C74A—C77A175.6 (9)
C31—C1—C41—C4652.9 (4)C73A—C74A—C75A—C76A1 (3)
C46—C41—C42—C430.8 (5)C77A—C74A—C75A—C76A177.3 (14)
C1—C41—C42—C43179.3 (3)C72A—N71A—C76A—C75A2 (2)
C41—C42—C43—C440.4 (5)C74A—C75A—C76A—N71A2 (3)
C42—C43—C44—C450.1 (5)C73A—C74A—C77A—C87A31.1 (18)
C43—C44—C45—C460.1 (5)C75A—C74A—C77A—C87A152.3 (13)
C44—C45—C46—C410.5 (5)C86A—N81A—C82A—C83A0.8 (13)
C42—C41—C46—C450.8 (5)N81A—C82A—C83A—C84A0.8 (13)
C1—C41—C46—C45179.3 (3)C82A—C83A—C84A—C85A0.6 (18)
O2—C2—C51—C52122.8 (3)C82A—C83A—C84A—C87A172.4 (9)
C61—C2—C51—C52119.6 (3)C83A—C84A—C85A—C86A3 (2)
C21—C2—C51—C523.5 (4)C87A—C84A—C85A—C86A169.6 (11)
O2—C2—C51—C5656.1 (3)C82A—N81A—C86A—C85A4 (2)
C61—C2—C51—C5661.5 (3)C84A—C85A—C86A—N81A6 (2)
C21—C2—C51—C56175.4 (2)C74A—C77A—C87A—C84A174.5 (10)
C56—C51—C52—C530.2 (5)C83A—C84A—C87A—C77A10.8 (16)
C2—C51—C52—C53178.7 (3)C85A—C84A—C87A—C77A176.5 (11)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O20.842.052.787 (3)147
O2—H2···N710.841.962.786 (4)168
(II) Ferrocene-1,1'-diylbis(diphenylmethanol)–1,6-diaminohexane top
Crystal data top
[Fe(C18H15O)2]2·C6H16N2Z = 1
Mr = 1217.11F(000) = 642
Triclinic, P1Dx = 1.307 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.2027 (2) ÅCell parameters from 6769 reflections
b = 11.7067 (2) Åθ = 3.0–27.6°
c = 14.6172 (3) ŵ = 0.52 mm1
α = 84.9780 (9)°T = 150 K
β = 70.2454 (8)°Block, orange
γ = 70.3612 (8)°0.40 × 0.30 × 0.28 mm
V = 1546.88 (5) Å3
Data collection top
KappaCCD
diffractometer
7106 independent reflections
Radiation source: fine-focus sealed X-ray tube6398 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
ϕ scans, and ω scans with κ offsetsθmax = 27.6°, θmin = 3.0°
Absorption correction: multi-scan
(DENZO-SMN; Otwinowski & Minor, 1997)
h = 013
Tmin = 0.818, Tmax = 0.867k = 1315
23031 measured reflectionsl = 1719
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)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.082H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0288P)2 + 0.7055P]
where P = (Fo2 + 2Fc2)/3
7106 reflections(Δ/σ)max = 0.002
391 parametersΔρmax = 0.30 e Å3
0 restraintsΔρmin = 0.49 e Å3
Crystal data top
[Fe(C18H15O)2]2·C6H16N2γ = 70.3612 (8)°
Mr = 1217.11V = 1546.88 (5) Å3
Triclinic, P1Z = 1
a = 10.2027 (2) ÅMo Kα radiation
b = 11.7067 (2) ŵ = 0.52 mm1
c = 14.6172 (3) ÅT = 150 K
α = 84.9780 (9)°0.40 × 0.30 × 0.28 mm
β = 70.2454 (8)°
Data collection top
KappaCCD
diffractometer
7106 independent reflections
Absorption correction: multi-scan
(DENZO-SMN; Otwinowski & Minor, 1997)
6398 reflections with I > 2σ(I)
Tmin = 0.818, Tmax = 0.867Rint = 0.032
23031 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0320 restraints
wR(F2) = 0.082H-atom parameters constrained
S = 1.03Δρmax = 0.30 e Å3
7106 reflectionsΔρmin = 0.49 e Å3
391 parameters
Special details top

Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm [Fox, G·C. & Holmes, K·C. (1966). Acta Cryst. 20, 886–891] which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Fe11.102756 (19)0.603013 (16)0.118594 (13)0.01850 (6)
O11.22021 (12)0.38833 (9)0.28265 (7)0.0288 (2)
O21.07938 (10)0.61792 (8)0.37540 (7)0.02193 (19)
C111.23957 (14)0.42780 (11)0.11478 (9)0.0199 (2)
C121.32152 (14)0.50991 (12)0.09818 (10)0.0238 (3)
C131.30528 (15)0.57778 (13)0.01473 (11)0.0272 (3)
C141.21479 (16)0.53766 (12)0.02141 (10)0.0256 (3)
C151.17368 (15)0.44508 (12)0.04011 (9)0.0217 (3)
C161.23792 (14)0.33436 (12)0.19344 (10)0.0214 (3)
C211.00859 (14)0.71657 (11)0.24063 (9)0.0198 (2)
C221.01670 (16)0.78399 (12)0.15362 (10)0.0246 (3)
C230.93524 (16)0.74973 (13)0.10425 (11)0.0286 (3)
C240.87772 (15)0.66159 (14)0.15982 (11)0.0281 (3)
C250.92310 (14)0.64044 (12)0.24339 (10)0.0231 (3)
C261.06110 (14)0.72875 (11)0.32413 (9)0.0193 (2)
C311.38735 (15)0.23218 (12)0.16780 (11)0.0232 (3)
C321.47966 (16)0.20220 (13)0.07243 (12)0.0311 (3)
C331.61345 (18)0.10722 (15)0.05239 (14)0.0412 (4)
C341.65518 (18)0.04294 (15)0.12717 (16)0.0433 (4)
C351.56311 (19)0.07138 (14)0.22220 (15)0.0404 (4)
C361.42965 (17)0.16554 (13)0.24287 (12)0.0313 (3)
C411.11510 (15)0.27965 (12)0.20722 (10)0.0241 (3)
C421.12952 (17)0.19521 (13)0.13971 (11)0.0291 (3)
C431.0161 (2)0.14910 (15)0.15039 (13)0.0387 (4)
C440.8879 (2)0.18578 (18)0.22908 (16)0.0489 (5)
C450.8743 (2)0.26717 (19)0.29748 (17)0.0539 (5)
C460.98691 (18)0.31386 (15)0.28673 (13)0.0379 (4)
C510.94642 (14)0.83301 (11)0.39521 (10)0.0210 (3)
C520.82726 (17)0.91660 (13)0.37523 (11)0.0303 (3)
C530.72539 (18)1.00727 (15)0.44409 (12)0.0376 (4)
C540.74232 (18)1.01431 (14)0.53279 (12)0.0364 (4)
C550.86129 (19)0.93061 (15)0.55342 (11)0.0348 (3)
C560.96293 (17)0.84131 (13)0.48512 (11)0.0286 (3)
C611.20986 (14)0.75042 (12)0.28661 (9)0.0210 (3)
C621.21892 (15)0.86237 (12)0.24903 (10)0.0246 (3)
C631.35396 (17)0.88200 (14)0.21146 (11)0.0304 (3)
C641.48202 (17)0.79038 (15)0.21195 (12)0.0348 (3)
C651.47408 (16)0.67947 (15)0.25065 (12)0.0339 (3)
C661.33900 (15)0.65931 (13)0.28788 (11)0.0270 (3)
N10.81471 (13)0.60480 (11)0.50091 (9)0.0276 (3)
C20.67658 (16)0.68502 (13)0.48746 (11)0.0287 (3)
C30.54495 (16)0.63958 (14)0.53022 (12)0.0317 (3)
C40.56871 (16)0.51897 (14)0.48401 (12)0.0320 (3)
H11.16960.46200.28540.043*
H20.99720.61740.41420.033*
H121.37730.51780.13630.029*
H131.34760.63920.01210.033*
H141.18650.56730.07690.031*
H151.11320.40240.03280.026*
H221.06720.84140.13230.029*
H230.92210.78080.04450.034*
H240.81910.62340.14400.034*
H250.90050.58500.29280.028*
H321.45170.24650.02060.037*
H331.67580.08690.01300.049*
H341.74690.02070.11350.052*
H351.59120.02630.27370.048*
H361.36710.18450.30840.038*
H421.21780.16890.08580.035*
H431.02680.09230.10350.046*
H440.80970.15530.23610.059*
H450.78710.29140.35230.065*
H460.97600.36980.33430.045*
H520.81440.91240.31430.036*
H530.64401.06440.42960.045*
H540.67311.07600.57940.044*
H550.87320.93450.61470.042*
H561.04480.78510.49960.034*
H621.13160.92600.24910.029*
H631.35850.95840.18540.036*
H641.57450.80340.18600.042*
H651.56150.61670.25180.041*
H661.33490.58300.31430.032*
H1A0.81280.61610.56220.041*
H1B0.82420.52610.49190.041*
H2A0.69380.69620.41690.034*
H2B0.65120.76550.51760.034*
H3A0.45670.70130.52090.038*
H3B0.52580.62980.60100.038*
H4A0.60160.52550.41240.038*
H4B0.64840.45490.50110.038*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.01683 (10)0.01760 (10)0.01911 (10)0.00334 (7)0.00503 (7)0.00244 (7)
O10.0383 (6)0.0212 (5)0.0238 (5)0.0009 (4)0.0143 (4)0.0038 (4)
O20.0215 (4)0.0191 (4)0.0229 (5)0.0048 (4)0.0064 (4)0.0015 (4)
C110.0167 (6)0.0180 (6)0.0204 (6)0.0017 (5)0.0034 (5)0.0037 (5)
C120.0161 (6)0.0224 (6)0.0291 (7)0.0040 (5)0.0040 (5)0.0043 (5)
C130.0223 (6)0.0235 (7)0.0278 (7)0.0070 (5)0.0016 (5)0.0012 (5)
C140.0290 (7)0.0235 (6)0.0182 (6)0.0047 (5)0.0034 (5)0.0020 (5)
C150.0233 (6)0.0198 (6)0.0197 (6)0.0043 (5)0.0058 (5)0.0042 (5)
C160.0215 (6)0.0192 (6)0.0217 (6)0.0033 (5)0.0074 (5)0.0022 (5)
C210.0169 (6)0.0183 (6)0.0212 (6)0.0014 (5)0.0056 (5)0.0045 (5)
C220.0285 (7)0.0173 (6)0.0256 (7)0.0016 (5)0.0113 (6)0.0024 (5)
C230.0290 (7)0.0253 (7)0.0273 (7)0.0043 (6)0.0152 (6)0.0062 (5)
C240.0172 (6)0.0338 (7)0.0307 (7)0.0012 (5)0.0083 (6)0.0131 (6)
C250.0166 (6)0.0259 (6)0.0234 (7)0.0048 (5)0.0029 (5)0.0060 (5)
C260.0197 (6)0.0173 (6)0.0200 (6)0.0044 (5)0.0068 (5)0.0006 (5)
C310.0204 (6)0.0176 (6)0.0334 (7)0.0051 (5)0.0113 (6)0.0024 (5)
C320.0261 (7)0.0245 (7)0.0366 (8)0.0032 (6)0.0071 (6)0.0026 (6)
C330.0271 (8)0.0307 (8)0.0524 (11)0.0008 (6)0.0027 (7)0.0079 (7)
C340.0260 (8)0.0256 (8)0.0745 (13)0.0020 (6)0.0202 (8)0.0063 (8)
C350.0381 (9)0.0271 (8)0.0630 (12)0.0023 (7)0.0336 (9)0.0014 (7)
C360.0333 (8)0.0253 (7)0.0388 (8)0.0052 (6)0.0199 (7)0.0008 (6)
C410.0226 (6)0.0212 (6)0.0269 (7)0.0063 (5)0.0082 (5)0.0059 (5)
C420.0311 (7)0.0295 (7)0.0295 (7)0.0134 (6)0.0112 (6)0.0051 (6)
C430.0460 (10)0.0366 (8)0.0461 (10)0.0237 (7)0.0233 (8)0.0118 (7)
C440.0371 (9)0.0474 (10)0.0700 (13)0.0274 (8)0.0172 (9)0.0157 (9)
C450.0319 (9)0.0516 (11)0.0645 (13)0.0195 (8)0.0068 (9)0.0016 (9)
C460.0315 (8)0.0334 (8)0.0395 (9)0.0115 (7)0.0012 (7)0.0008 (7)
C510.0203 (6)0.0191 (6)0.0217 (6)0.0066 (5)0.0034 (5)0.0028 (5)
C520.0304 (7)0.0270 (7)0.0274 (7)0.0004 (6)0.0097 (6)0.0044 (6)
C530.0343 (8)0.0294 (8)0.0364 (9)0.0045 (6)0.0086 (7)0.0073 (6)
C540.0376 (8)0.0280 (7)0.0313 (8)0.0041 (6)0.0001 (7)0.0109 (6)
C550.0420 (9)0.0355 (8)0.0242 (7)0.0103 (7)0.0077 (7)0.0085 (6)
C560.0301 (7)0.0286 (7)0.0264 (7)0.0066 (6)0.0104 (6)0.0040 (6)
C610.0207 (6)0.0228 (6)0.0195 (6)0.0064 (5)0.0063 (5)0.0037 (5)
C620.0240 (7)0.0226 (6)0.0271 (7)0.0067 (5)0.0085 (6)0.0022 (5)
C630.0303 (7)0.0290 (7)0.0334 (8)0.0142 (6)0.0078 (6)0.0004 (6)
C640.0236 (7)0.0399 (9)0.0410 (9)0.0139 (6)0.0062 (6)0.0024 (7)
C650.0209 (7)0.0360 (8)0.0418 (9)0.0054 (6)0.0101 (6)0.0002 (7)
C660.0235 (7)0.0258 (7)0.0309 (7)0.0058 (5)0.0102 (6)0.0001 (6)
N10.0270 (6)0.0301 (6)0.0263 (6)0.0112 (5)0.0084 (5)0.0027 (5)
C20.0256 (7)0.0280 (7)0.0292 (7)0.0079 (6)0.0057 (6)0.0004 (6)
C30.0247 (7)0.0320 (8)0.0340 (8)0.0086 (6)0.0039 (6)0.0028 (6)
C40.0257 (7)0.0330 (8)0.0361 (8)0.0101 (6)0.0071 (6)0.0026 (6)
Geometric parameters (Å, º) top
Fe1—C232.0301 (13)C35—H350.95
Fe1—C222.0390 (13)C36—H360.95
Fe1—C152.0419 (12)C41—C461.387 (2)
Fe1—C242.0454 (14)C41—C421.395 (2)
Fe1—C142.0458 (13)C42—C431.392 (2)
Fe1—C112.0498 (12)C42—H420.95
Fe1—C132.0517 (14)C43—C441.382 (3)
Fe1—C252.0540 (13)C43—H430.95
Fe1—C122.0567 (13)C44—C451.383 (3)
Fe1—C212.0665 (12)C44—H440.95
O1—C161.4284 (15)C45—C461.389 (3)
O1—H10.84C45—H450.95
O2—C261.4288 (15)C46—H460.95
O2—H20.84C51—C521.3824 (19)
C11—C121.4298 (19)C51—C561.3957 (19)
C11—C151.4319 (18)C52—C531.399 (2)
C11—C161.5159 (18)C52—H520.95
C12—C131.423 (2)C53—C541.377 (2)
C12—H120.95C53—H530.95
C13—C141.420 (2)C54—C551.386 (2)
C13—H130.95C54—H540.95
C14—C151.428 (2)C55—C561.385 (2)
C14—H140.95C55—H550.95
C15—H150.95C56—H560.95
C16—C311.5369 (17)C61—C661.3937 (18)
C16—C411.5386 (19)C61—C621.3961 (19)
C21—C221.4298 (19)C62—C631.390 (2)
C21—C251.4315 (18)C62—H620.95
C21—C261.5235 (17)C63—C641.386 (2)
C22—C231.4327 (19)C63—H630.95
C22—H220.95C64—C651.387 (2)
C23—C241.417 (2)C64—H640.95
C23—H230.95C65—C661.393 (2)
C24—C251.421 (2)C65—H650.95
C24—H240.95C66—H660.95
C25—H250.95N1—C21.4738 (18)
C26—C611.5299 (18)N1—H1A0.91
C26—C511.5422 (17)N1—H1B0.91
C31—C321.389 (2)C2—C31.527 (2)
C31—C361.394 (2)C2—H2A0.99
C32—C331.397 (2)C2—H2B0.99
C32—H320.95C3—C41.528 (2)
C33—C341.378 (3)C3—H3A0.99
C33—H330.95C3—H3B0.99
C34—C351.383 (3)C4—C4i1.523 (3)
C34—H340.95C4—H4A0.99
C35—C361.390 (2)C4—H4B0.99
C16—O1—H1109.5C44—C43—H43120.0
C26—O2—H2109.5C42—C43—H43120.0
C12—C11—C15107.41 (12)C43—C44—C45119.44 (16)
C12—C11—C16123.97 (12)C43—C44—H44120.3
C15—C11—C16128.43 (12)C45—C44—H44120.3
C13—C12—C11108.35 (12)C44—C45—C46120.60 (18)
C13—C12—H12125.8C44—C45—H45119.7
C11—C12—H12125.8C46—C45—H45119.7
C14—C13—C12108.09 (12)C41—C46—C45120.63 (17)
C14—C13—H13126.0C41—C46—H46119.7
C12—C13—H13126.0C45—C46—H46119.7
C13—C14—C15108.14 (12)C52—C51—C56118.63 (12)
C13—C14—H14125.9C52—C51—C26123.48 (12)
C15—C14—H14125.9C56—C51—C26117.87 (12)
C14—C15—C11108.02 (12)C51—C52—C53120.47 (14)
C14—C15—H15126.0C51—C52—H52119.8
C11—C15—H15126.0C53—C52—H52119.8
O1—C16—C11109.85 (10)C54—C53—C52120.44 (15)
O1—C16—C31105.48 (10)C54—C53—H53119.8
C11—C16—C31110.30 (11)C52—C53—H53119.8
O1—C16—C41110.49 (11)C53—C54—C55119.40 (14)
C11—C16—C41111.26 (11)C53—C54—H54120.3
C31—C16—C41109.31 (10)C55—C54—H54120.3
C22—C21—C25107.19 (11)C56—C55—C54120.29 (14)
C22—C21—C26129.21 (12)C56—C55—H55119.9
C25—C21—C26123.22 (12)C54—C55—H55119.9
C21—C22—C23107.99 (13)C55—C56—C51120.77 (14)
C21—C22—H22126.0C55—C56—H56119.6
C23—C22—H22126.0C51—C56—H56119.6
C24—C23—C22108.21 (12)C66—C61—C62118.54 (13)
C24—C23—H23125.9C66—C61—C26121.19 (12)
C22—C23—H23125.9C62—C61—C26120.26 (11)
C23—C24—C25107.97 (12)C63—C62—C61120.92 (13)
C23—C24—H24126.0C63—C62—H62119.5
C25—C24—H24126.0C61—C62—H62119.5
C24—C25—C21108.63 (13)C64—C63—C62120.12 (14)
C24—C25—H25125.7C64—C63—H63119.9
C21—C25—H25125.7C62—C63—H63119.9
O2—C26—C21108.43 (10)C63—C64—C65119.47 (14)
O2—C26—C61107.96 (10)C63—C64—H64120.3
C21—C26—C61111.27 (11)C65—C64—H64120.3
O2—C26—C51108.67 (10)C64—C65—C66120.55 (14)
C21—C26—C51110.63 (10)C64—C65—H65119.7
C61—C26—C51109.79 (10)C66—C65—H65119.7
C32—C31—C36119.04 (13)C65—C66—C61120.38 (14)
C32—C31—C16122.26 (12)C65—C66—H66119.8
C36—C31—C16118.68 (13)C61—C66—H66119.8
C31—C32—C33120.31 (15)C2—N1—H1A109.5
C31—C32—H32119.8C2—N1—H1B109.5
C33—C32—H32119.8H1A—N1—H1B109.5
C34—C33—C32120.21 (17)N1—C2—C3114.98 (12)
C34—C33—H33119.9N1—C2—H2A108.5
C32—C33—H33119.9C3—C2—H2A108.5
C33—C34—C35119.80 (14)N1—C2—H2B108.5
C33—C34—H34120.1C3—C2—H2B108.5
C35—C34—H34120.1H2A—C2—H2B107.5
C34—C35—C36120.42 (16)C2—C3—C4112.94 (12)
C34—C35—H35119.8C2—C3—H3A109.0
C36—C35—H35119.8C4—C3—H3A109.0
C35—C36—C31120.21 (16)C2—C3—H3B109.0
C35—C36—H36119.9C4—C3—H3B109.0
C31—C36—H36119.9H3A—C3—H3B107.8
C46—C41—C42118.45 (14)C4i—C4—C3113.48 (16)
C46—C41—C16120.72 (13)C4i—C4—H4A108.9
C42—C41—C16120.84 (13)C3—C4—H4A108.9
C43—C42—C41120.77 (15)C4i—C4—H4B108.9
C43—C42—H42119.6C3—C4—H4B108.9
C41—C42—H42119.6H4A—C4—H4B107.7
C44—C43—C42120.08 (17)
C15—C11—C12—C130.49 (14)C31—C16—C41—C46133.38 (14)
C16—C11—C12—C13175.90 (11)O1—C16—C41—C42162.76 (12)
C11—C12—C13—C140.55 (15)C11—C16—C41—C4274.95 (15)
C12—C13—C14—C150.40 (15)C31—C16—C41—C4247.10 (17)
C13—C14—C15—C110.09 (15)C46—C41—C42—C431.9 (2)
C12—C11—C15—C140.25 (14)C16—C41—C42—C43177.65 (13)
C16—C11—C15—C14175.38 (12)C41—C42—C43—C440.7 (2)
C12—C11—C16—O145.02 (16)C42—C43—C44—C450.9 (3)
C15—C11—C16—O1140.59 (13)C43—C44—C45—C461.2 (3)
C12—C11—C16—C3170.83 (15)C42—C41—C46—C451.5 (2)
C15—C11—C16—C31103.56 (15)C16—C41—C46—C45178.03 (16)
C12—C11—C16—C41167.69 (12)C44—C45—C46—C410.0 (3)
C15—C11—C16—C4117.92 (18)O2—C26—C51—C52130.03 (14)
C25—C21—C22—C230.54 (14)C21—C26—C51—C5211.09 (18)
C26—C21—C22—C23172.45 (12)C61—C26—C51—C52112.09 (15)
C21—C22—C23—C240.25 (15)O2—C26—C51—C5648.62 (16)
C22—C23—C24—C250.15 (15)C21—C26—C51—C56167.55 (12)
C23—C24—C25—C210.49 (15)C61—C26—C51—C5669.26 (15)
C22—C21—C25—C240.64 (14)C56—C51—C52—C530.2 (2)
C26—C21—C25—C24172.87 (11)C26—C51—C52—C53178.47 (14)
C22—C21—C26—O2159.11 (12)C51—C52—C53—C540.1 (3)
C25—C21—C26—O228.89 (16)C52—C53—C54—C550.0 (3)
C22—C21—C26—C6140.52 (17)C53—C54—C55—C560.5 (3)
C25—C21—C26—C61147.48 (12)C54—C55—C56—C510.9 (2)
C22—C21—C26—C5181.81 (16)C52—C51—C56—C550.7 (2)
C25—C21—C26—C5190.19 (14)C26—C51—C56—C55178.05 (14)
O1—C16—C31—C32144.88 (13)O2—C26—C61—C6612.33 (16)
C11—C16—C31—C3226.32 (17)C21—C26—C61—C66106.54 (14)
C41—C16—C31—C3296.30 (15)C51—C26—C61—C66130.65 (13)
O1—C16—C31—C3636.75 (16)O2—C26—C61—C62168.48 (11)
C11—C16—C31—C36155.31 (12)C21—C26—C61—C6272.65 (15)
C41—C16—C31—C3682.07 (15)C51—C26—C61—C6250.17 (16)
C36—C31—C32—C330.5 (2)C66—C61—C62—C631.5 (2)
C16—C31—C32—C33178.90 (14)C26—C61—C62—C63177.67 (12)
C31—C32—C33—C340.3 (3)C61—C62—C63—C640.8 (2)
C32—C33—C34—C351.1 (3)C62—C63—C64—C650.4 (2)
C33—C34—C35—C360.9 (3)C63—C64—C65—C660.7 (2)
C34—C35—C36—C310.1 (2)C64—C65—C66—C610.1 (2)
C32—C31—C36—C350.7 (2)C62—C61—C66—C651.2 (2)
C16—C31—C36—C35179.09 (13)C26—C61—C66—C65178.01 (13)
O1—C16—C41—C4617.73 (18)N1—C2—C3—C461.89 (18)
C11—C16—C41—C46104.57 (15)C2—C3—C4—C4i172.22 (16)
Symmetry code: (i) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O20.842.092.8021 (13)142
O2—H2···N10.841.912.7499 (16)176
N1—H1A···O1ii0.912.183.0669 (16)166
Symmetry code: (ii) x+2, y+1, z+1.

Experimental details

(I)(II)
Crystal data
Chemical formula[Fe(C18H15O)2]·C12H10N2[Fe(C18H15O)2]2·C6H16N2
Mr732.671217.11
Crystal system, space groupTriclinic, P1Triclinic, P1
Temperature (K)150150
a, b, c (Å)9.6393 (4), 11.4219 (5), 17.7338 (10)10.2027 (2), 11.7067 (2), 14.6172 (3)
α, β, γ (°)76.7680 (18), 87.4580 (17), 74.064 (3)84.9780 (9), 70.2454 (8), 70.3612 (8)
V3)1827.24 (15)1546.88 (5)
Z21
Radiation typeMo KαMo Kα
µ (mm1)0.460.52
Crystal size (mm)0.23 × 0.16 × 0.140.40 × 0.30 × 0.28
Data collection
DiffractometerKappaCCD
diffractometer
KappaCCD
diffractometer
Absorption correctionMulti-scan
(DENZO-SMN; Otwinowski & Minor, 1997)
Multi-scan
(DENZO-SMN; Otwinowski & Minor, 1997)
Tmin, Tmax0.902, 0.9390.818, 0.867
No. of measured, independent and
observed [I > 2σ(I)] reflections
16969, 6460, 4709 23031, 7106, 6398
Rint0.0600.032
(sin θ/λ)max1)0.5960.651
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.050, 0.125, 1.03 0.032, 0.082, 1.03
No. of reflections64607106
No. of parameters526391
No. of restraints640
H-atom treatmentH-atom parameters constrainedH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.55, 0.480.30, 0.49

Computer programs: KappaCCD Server Software (Nonius, 1997), DENZO-SMN (Otwinowski & Minor, 1997), DENZO-SMN, SHELXS97 (Sheldrick, 1997), PLATON (Spek, 2001), SHELXL97 (Sheldrick, 1997) and PRPKAPPA (Ferguson, 1999).

Selected torsion angles (º) for (I) top
C73—C74—C77—C87161.5 (6)C73A—C74A—C77A—C87A31.1 (18)
C75—C74—C77—C8717.1 (10)C75A—C74A—C77A—C87A152.3 (13)
C83—C84—C87—C77139.5 (6)C83A—C84A—C87A—C77A10.8 (16)
C85—C84—C87—C7741.2 (8)C85A—C84A—C87A—C77A176.5 (11)
Hydrogen-bond geometry (Å, º) for (I) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O20.842.052.787 (3)147
O2—H2···N710.841.962.786 (4)168
Selected torsion angles (º) for (II) top
N1—C2—C3—C461.89 (18)C2—C3—C4—C4i172.22 (16)
Symmetry code: (i) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) for (II) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O20.842.092.8021 (13)142
O2—H2···N10.841.912.7499 (16)176
N1—H1A···O1ii0.912.183.0669 (16)166
Symmetry code: (ii) x+2, y+1, z+1.
 

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