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In the title compound, 2[Fe(C5H5)(C6H5O2)]·C6H12N2, the molecular components are linked into finite three-component aggregates by strong O-H...N hydrogen bonds [O...N 2.578 (4) and 2.604 (5) Å; O-H...N 170 (5) and 174 (6)°]; these aggregates are further linked by C-H...O hydrogen bonds [C...O 3.327 (5)-3.401 (5) Å; C-H...O 149-157°] into continuous sheets in the form of (6,3) nets.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270101004978/sk1469sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270101004978/sk1469Isup2.hkl
Contains datablock I

CCDC reference: 166964

Comment top

The trigonally trisubstituted acid 3,5-dinitrobenzoic acid forms adducts with a wide range of ditertiary amines having stoichiometry (acid)2.(base) (Burchell, Glidewell et al., 2001). In each of these adducts, where proton transfer from acid to amine is complete to give salts, the basic structural motif is a three-component centrosymmetric aggregate, anion-cation-anion, in which the components are linked by N—H···O hydrogen bonds. Since there is an excess of hydrogen-bond acceptors, in the form of the four nitro groups per aggregate, over hard hydrogen-bond donors, C—H···O hydrogen bonds are formed which link the finite three-component aggregates into continuous arrays, which can be one-, two- or three-dimensional, as exemplified by the adducts formed by N,N,N',N'-tetramethyl-1,2-diaminoethane (Me2NCH2CH2NMe2), 1,4-diazabicyclo[2.2.2]octane [N(CH2CH2)3N] and N,N'-dimethylpiperazine [MeN(CH2CH2)2NMe], respectively.

Seeking to develop analogous systems in which the acid component contains instead an excess of soft hydrogen-bond donors over acceptors, we have now turned to ferrocenecarboxylic acid [FcCOOH = (C5H5)Fe(C5H4COOH)] as the acid component, and we report here the structure of its 2:1 adduct, (I), with 1,4-diazabicyclo[2.2.2]octane (DABCO). \sch

Co-crystallization of FcCOOH with DABCO provides the 2:1 adduct (C11H10FeO2)2·(C6H12N2), as expected, in which the three-molecular components within the asymmetric unit (Fig. 1) are linked by two O—H···N hydrogen bonds, rather than by N—H···O hydrogen bonds as in the corresponding adduct formed by 3,5-dinitrobenzoic acid (Burchell, Glidewell et al., 2001). These two hydrogen bonds both have very short O···N distances, associated with nearly linear O—H···N arrays (Table 2): it may thus be deduced that these hydrogen bonds are strong for their types. Consistent with the short O···N distances, the O—H distances (Table 2) are somewhat longer than those normally found in carboxylic acids: in general, short D···A distances are associated with long D—H distances, culminating in very short D···A distances having approximately centred H atoms (Emsley, 1980; Aakeröy & Seddon, 1993). The marked difference between the C—O and CO bond lengths is consistent with the neutral character of all the molecular components.

Apart from the C and H atoms of the DABCO, the three-component aggregate (Fig. 1) is close to being centrosymmetric: indeed the ferrocene units alone form an almost centrosymmetric array, corresponding to a P21/c structure whose unit cell can be generated from the observed cell by the transformation (0.5 0 0.5/0 1 0/-1 0 0). The fully ordered nature of the DABCO unit in (I) precludes the occurrence of any additional symmetry. It is, however, necessary to note here that DABCO has been observed (Ferguson et al., 1998) disordered across a centre of inversion in the 1:1 adduct with 4,4'-biphenol. It is possible that in that adduct, the disordered model deduced from the X-ray diffraction data is, in fact, a static representation of a dynamic system, where the C atom sites correspond to local minima in the rotation of the DABCO unit around its N···N vector. Such a motion, consisting of 60° jumps, would be prevented in compound (I) by the C—H···O hydrogen bonds formed by the DABCO component (see below).

In the FcCOOH components, there are no significant differences in either the Fe—C distances or in the ring C—C distances, either between the two independent units or between the two types of ring, substituted and unsubstituted. In each FcCOOH molecule, the two rings are almost fully eclipsed: the mean values of the C—Cg(A)—Cg(B) C torsion angles [where Cg(A) and Cg(B) represent the centroids of the two rings in that molecule] are 2.1 (2)° in molecule 1 (containing Fe1) and 0.4 (2)° in molecule 2 (containing Fe2): the corresponding Cg—Fe—Cg angles are 177.65 (11) and 178.36 (10)°. In each molecule, the carboxyl substituent is essentially coplanar with the adjacent ring with these groups twisted out of the plane of the adjacent ring by 3.3 (2) and 6.3 (2)° in molecules 1 and 2, respectively. The DABCO component shows the usual twist (Table 1) from idealized D3 h (-6m2) symmetry to D3 (32) consequent upon the eclipsing of the C—H bonds which is required in the D3 h conformation. Despite the shortness of the O—H···N hydrogen bonds discussed earlier, the C—N distances, mean value 1.477 (5) Å, are typical of those in unprotonated DABCO units. For comparison, in the two independent monoprotonated [H(DABCO)]+ units in the 3,5-dihydroxybenzoate salt (Burchell, Ferguson et al., 2001), the C—N bonds at the unprotonated N have mean value 1.473 (3) Å, with range 1.466 (3)–1.480 (2) Å, while those at the protonated N have mean value 1.493 (3) Å, with range 1.486 (2)–1.498 (2) Å.

The three-component aggregates are linked into continuous sheets by means of C—H···O hydrogen bonds (Table 2), in which the carbonyl O atoms O12 and O22 (Fig. 1) act as the acceptors. Ferrocene C13 at (-x, 0.5 + y, 1.5 - z) acts as hydrogen-bond donor to O22 at (x, y, z), while C13 at (x, y, z) in turn acts as hydrogen-bond donor to O22 at (-x, -0.5 + y, 1.5 - z), so generating a C33(15) spiral chain around the 21 screw axis along (0, y, 3/4) (Fig. 2). A second spiral chain of this type, related to the first by the centres of inversion and thus running anti-parallel to it, lies around the 21 axis along (0, y, 1/4). These spiral chains are linked to form sheets by paired C—H···O hydrogen bonds. Atoms C42 and C52 in the DABCO unit at (x, y, z) both act as hydrogen-bond donors, via H42A and H52Bl, respectively, to O12 at (-x, 1 - y, 1 - z): these two hydrogen bonds thus generate a local R12(6) rings, and propagation by the centre of inversion at (0, 1/2, 1/2) generates an R44(16) ring containing two FcCOOH and two DABCO units (Fig. 3). Each three-component aggregate is thus linked to three other such aggregates, two within a spiral chain along [010] and the third within the R44(16) ring: the combination of the C33(15) and R44(16) motifs thus generates a sheet parallel to (100) in the form of a (6,3) net (Batten & Robson, 1998) (Fig. 4).

Related literature top

For related literature, see: Aakeröy & Seddon (1993); Batten & Robson (1998); Burchell, Ferguson, Lough, Gregson & Glidewell (2001); Burchell, Glidewell, Lough & Ferguson (2001); Emsley (1980); Ferguson et al. (1998).

Experimental top

Stoichiometric quantities of FcCOOH and DABCO were separately dissolved in methanol; the solutions were mixed and the mixture was set aside to crystallize, producing analytically pure (I). Analysis: found C 58.6, H 5.4, N 4.4%; C28H32Fe2N2O4 requires C 58.8, H 5.6, N 4.9%. Crystals suitable for single-crystal X-ray diffraction were selected directly from the analytical sample.

Refinement top

Compound (I) crystallized in the monoclinic system; space group P21/c was uniquely assigned from the systematic absences. H atoms bonded to C were treated as riding atoms with C—H 0.95 Å (FcCOOH) and 0.99 Å (DABCO). Hydroxy H atoms H1 and H2 were refined isotropically.

Computing details top

Data collection: Kappa-CCD 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 and PRPKAPPA (Ferguson, 1999).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. Part of the crystal structure of (I) showing formation of a C33(15) spiral parallel to [010]. For the sake of clarity, H atoms not participating in the motif shown are omitted. The atoms marked with a star (*) or hash (#) are at the symmetry positions (-x, -1/2 + y, 3/2 - z) and (-x, 1/2 + y, 3/2 - z), respectively.
[Figure 3] Fig. 3. Part of the crystal structure of (I) showing formation of a centrosymmetric R44(16) ring with R12(6) rings embedded. For the sake of clarity, H atoms not participating in the motif shown are omitted. The atoms marked with a star (*) are at the symmetry position (-x, 1 - y, 1 - z).
[Figure 4] Fig. 4. Part of the crystal structure of (I) showing formation of a (6,3) net parallel to (100).
Ferrocenecarboxylic acid–1,4-diazabicyclo[2.2.2]octane (2/1) top
Crystal data top
[Fe(C5H5)(C6H5O2)]2·C6H12N2F(000) = 1192
Mr = 572.26Dx = 1.522 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 11.3900 (2) ÅCell parameters from 4385 reflections
b = 21.2256 (6) Åθ = 2.8–25.0°
c = 11.7248 (3) ŵ = 1.20 mm1
β = 118.2144 (12)°T = 150 K
V = 2497.79 (10) Å3Needle, orange
Z = 40.18 × 0.07 × 0.06 mm
Data collection top
Kappa-CCD
diffractometer
4385 independent reflections
Radiation source: fine-focus sealed X-ray tube2722 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.10
ϕ scans, and ω scans with κ offsetsθmax = 25.0°, θmin = 2.8°
Absorption correction: multi-scan
(DENZO-SMN; Otwinowski & Minor, 1997)
h = 013
Tmin = 0.813, Tmax = 0.932k = 025
4527 measured reflectionsl = 1312
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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104H atoms treated by a mixture of independent and constrained refinement
S = 0.99 w = 1/[σ2(Fo2) + (0.0334P)2]
where P = (Fo2 + 2Fc2)/3
4385 reflections(Δ/σ)max = 0.001
333 parametersΔρmax = 0.37 e Å3
0 restraintsΔρmin = 0.44 e Å3
Crystal data top
[Fe(C5H5)(C6H5O2)]2·C6H12N2V = 2497.79 (10) Å3
Mr = 572.26Z = 4
Monoclinic, P21/cMo Kα radiation
a = 11.3900 (2) ŵ = 1.20 mm1
b = 21.2256 (6) ÅT = 150 K
c = 11.7248 (3) Å0.18 × 0.07 × 0.06 mm
β = 118.2144 (12)°
Data collection top
Kappa-CCD
diffractometer
4385 independent reflections
Absorption correction: multi-scan
(DENZO-SMN; Otwinowski & Minor, 1997)
2722 reflections with I > 2σ(I)
Tmin = 0.813, Tmax = 0.932Rint = 0.10
4527 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.104H atoms treated by a mixture of independent and constrained refinement
S = 0.99Δρmax = 0.37 e Å3
4385 reflectionsΔρmin = 0.44 e Å3
333 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.

Geometry. Mean-plane data from the final SHELXL97 refinement run:-

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Fe10.30212 (5)0.32894 (2)0.73618 (6)0.02281 (17)
C110.1448 (3)0.30944 (18)0.7054 (4)0.0216 (9)
C120.2636 (3)0.28326 (18)0.6059 (4)0.0242 (9)
C130.3145 (4)0.23996 (18)0.6632 (4)0.0269 (10)
C140.2277 (4)0.23994 (18)0.7988 (4)0.0277 (10)
C150.1232 (4)0.28267 (18)0.8256 (4)0.0240 (9)
C160.3229 (4)0.4241 (2)0.7275 (5)0.0396 (11)
C170.4399 (4)0.3956 (2)0.6308 (4)0.0377 (11)
C180.4901 (4)0.3558 (2)0.6939 (4)0.0367 (11)
C190.4051 (4)0.3596 (2)0.8286 (4)0.0394 (12)
C1100.3007 (4)0.4020 (2)0.8501 (5)0.0422 (12)
C1110.0636 (4)0.35888 (18)0.6869 (4)0.0239 (9)
O110.0382 (2)0.37875 (13)0.7952 (3)0.0273 (7)
O120.0882 (2)0.37755 (13)0.5786 (3)0.0335 (7)
Fe20.80577 (5)0.68571 (2)0.77234 (6)0.02123 (17)
C210.6405 (4)0.70488 (18)0.7895 (4)0.0214 (9)
C220.6289 (4)0.73248 (17)0.6728 (4)0.0228 (9)
C230.7354 (4)0.77554 (18)0.7087 (4)0.0268 (10)
C240.8144 (4)0.77451 (18)0.8457 (4)0.0267 (10)
C250.7561 (3)0.73115 (18)0.8960 (4)0.0240 (9)
C260.8185 (4)0.59010 (19)0.7716 (4)0.0343 (11)
C270.8109 (4)0.6153 (2)0.6564 (4)0.0378 (11)
C280.9213 (4)0.65610 (19)0.6923 (4)0.0298 (10)
C290.9959 (4)0.65638 (19)0.8285 (4)0.0290 (10)
C2100.9332 (4)0.61524 (19)0.8782 (4)0.0326 (10)
C2110.5560 (3)0.65521 (18)0.8020 (4)0.0226 (9)
O210.4630 (3)0.63272 (13)0.6895 (3)0.0285 (7)
O220.5702 (2)0.63807 (12)0.9071 (2)0.0289 (7)
N10.1798 (3)0.45997 (14)0.7505 (3)0.0220 (7)
N20.3182 (3)0.54638 (15)0.7207 (3)0.0247 (8)
C310.3133 (4)0.4624 (2)0.8640 (4)0.0429 (12)
C320.4001 (4)0.5109 (2)0.8408 (4)0.0365 (11)
C410.1140 (4)0.52135 (18)0.7351 (4)0.0339 (11)
C420.2021 (4)0.57453 (17)0.7257 (4)0.0279 (9)
C510.1942 (4)0.4470 (2)0.6341 (4)0.0351 (11)
C520.2686 (4)0.50188 (18)0.6096 (4)0.0286 (10)
H120.30240.29310.51630.029*
H130.39280.21530.61880.032*
H140.23830.21530.86090.033*
H150.05140.29200.90860.029*
H160.26820.45320.71270.047*
H170.47770.40200.54010.045*
H180.56820.33070.65260.044*
H190.41600.33750.89350.047*
H1100.22910.41360.93160.051*
H10.091 (5)0.411 (2)0.767 (5)0.095 (18)*
H220.56200.72350.58710.027*
H230.75160.80090.65080.032*
H240.89250.79870.89490.032*
H250.78800.72120.98480.029*
H260.75720.56130.77660.041*
H270.74400.60640.57070.045*
H280.94160.67930.63450.036*
H291.07460.68010.87830.035*
H2100.96270.60610.96690.039*
H20.406 (6)0.602 (3)0.704 (6)0.13 (2)*
H31A0.35550.42030.87930.051*
H31B0.30550.47440.94180.051*
H32A0.44040.54030.91490.044*
H32B0.47310.48900.83370.044*
H41A0.09830.52920.81000.041*
H41B0.02670.52100.65580.041*
H42A0.14970.60000.64690.033*
H42B0.23280.60260.80190.033*
H51A0.10510.44180.55820.042*
H51B0.24450.40730.64610.042*
H52A0.34450.48530.59960.034*
H52B0.20770.52410.52880.034*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.0205 (3)0.0217 (3)0.0289 (4)0.0001 (3)0.0139 (3)0.0002 (3)
C110.021 (2)0.022 (2)0.023 (2)0.0014 (17)0.0119 (18)0.0012 (18)
C120.023 (2)0.026 (2)0.024 (2)0.0016 (17)0.0120 (19)0.0021 (19)
C130.027 (2)0.023 (2)0.037 (3)0.0050 (18)0.020 (2)0.005 (2)
C140.035 (2)0.022 (2)0.035 (3)0.0001 (18)0.024 (2)0.001 (2)
C150.020 (2)0.028 (3)0.025 (2)0.0019 (17)0.0111 (19)0.0038 (19)
C160.039 (3)0.019 (2)0.067 (4)0.003 (2)0.030 (3)0.001 (2)
C170.032 (3)0.037 (3)0.046 (3)0.010 (2)0.020 (2)0.004 (2)
C180.026 (2)0.030 (3)0.055 (3)0.0034 (19)0.020 (2)0.001 (2)
C190.045 (3)0.039 (3)0.052 (3)0.015 (2)0.037 (3)0.009 (2)
C1100.031 (3)0.044 (3)0.047 (3)0.009 (2)0.014 (2)0.019 (3)
C1110.020 (2)0.022 (2)0.032 (3)0.0046 (17)0.013 (2)0.003 (2)
O110.0256 (15)0.0288 (18)0.0278 (17)0.0067 (12)0.0128 (14)0.0010 (13)
O120.0287 (16)0.042 (2)0.0294 (18)0.0053 (13)0.0136 (14)0.0095 (14)
Fe20.0201 (3)0.0205 (3)0.0253 (4)0.0013 (2)0.0126 (3)0.0018 (3)
C210.023 (2)0.018 (2)0.031 (2)0.0001 (16)0.0189 (19)0.0009 (18)
C220.025 (2)0.021 (2)0.026 (2)0.0021 (17)0.0149 (19)0.0006 (18)
C230.032 (2)0.026 (2)0.033 (3)0.0015 (18)0.024 (2)0.0004 (19)
C240.029 (2)0.024 (2)0.031 (3)0.0077 (18)0.017 (2)0.0095 (19)
C250.024 (2)0.024 (2)0.023 (2)0.0001 (17)0.0104 (19)0.0006 (18)
C260.033 (2)0.019 (2)0.056 (3)0.0040 (19)0.026 (2)0.004 (2)
C270.034 (3)0.039 (3)0.040 (3)0.014 (2)0.017 (2)0.011 (2)
C280.032 (2)0.031 (3)0.036 (3)0.004 (2)0.023 (2)0.001 (2)
C290.021 (2)0.028 (3)0.037 (3)0.0020 (18)0.013 (2)0.002 (2)
C2100.034 (2)0.032 (3)0.030 (3)0.006 (2)0.014 (2)0.003 (2)
C2110.018 (2)0.021 (2)0.030 (3)0.0053 (17)0.0114 (19)0.0042 (19)
O210.0252 (16)0.0312 (18)0.0270 (17)0.0073 (13)0.0107 (14)0.0003 (14)
O220.0298 (16)0.0315 (18)0.0276 (17)0.0074 (12)0.0152 (14)0.0019 (14)
N10.0216 (17)0.0140 (18)0.026 (2)0.0003 (13)0.0081 (16)0.0002 (15)
N20.0162 (17)0.022 (2)0.030 (2)0.0030 (14)0.0055 (15)0.0006 (16)
C310.030 (2)0.042 (3)0.043 (3)0.008 (2)0.006 (2)0.019 (2)
C320.025 (2)0.035 (3)0.034 (3)0.0050 (19)0.001 (2)0.014 (2)
C410.035 (2)0.021 (2)0.052 (3)0.0031 (19)0.026 (2)0.001 (2)
C420.035 (2)0.016 (2)0.035 (3)0.0036 (19)0.019 (2)0.002 (2)
C510.040 (2)0.034 (3)0.039 (3)0.012 (2)0.024 (2)0.006 (2)
C520.034 (2)0.023 (2)0.035 (3)0.0018 (19)0.022 (2)0.003 (2)
Geometric parameters (Å, º) top
Fe1—C112.031 (3)C21—C251.432 (5)
Fe1—C122.025 (4)C21—C2111.481 (5)
Fe1—C132.051 (4)C22—C231.415 (5)
Fe1—C142.059 (4)C22—H220.95
Fe1—C152.049 (4)C23—C241.423 (5)
Fe1—C162.030 (4)C23—H230.95
Fe1—C172.038 (4)C24—C251.416 (5)
Fe1—C182.038 (4)C24—H240.95
Fe1—C192.044 (4)C25—H250.95
Fe1—C1102.042 (4)C26—C271.417 (6)
C11—C121.417 (5)C26—C2101.417 (5)
C11—C151.430 (5)C26—H260.95
C11—C1111.481 (5)C27—C281.418 (5)
C12—C131.414 (5)C27—H270.95
C12—H120.95C28—C291.410 (5)
C13—C141.421 (5)C28—H280.95
C13—H130.95C29—C2101.417 (5)
C14—C151.409 (5)C29—H290.95
C14—H140.95C210—H2100.95
C15—H150.95N1—C311.474 (5)
C16—C171.414 (6)N1—C411.471 (5)
C16—C1101.415 (6)N1—C511.476 (5)
C16—H160.95N1—H11.52 (5)
C17—C181.409 (5)C211—O221.220 (4)
C17—H170.95C211—O211.330 (4)
C18—C191.412 (6)O21—H20.99 (7)
C18—H180.95N2—C321.477 (5)
C19—C1101.417 (6)N2—C421.477 (4)
C19—H190.95N2—C521.487 (5)
C110—H1100.95C31—C321.538 (5)
C111—O121.229 (4)C31—H31A0.99
C111—O111.320 (4)C31—H31B0.99
O11—H11.06 (6)C32—H32A0.99
Fe2—C212.027 (3)C32—H32B0.99
Fe2—C222.045 (4)C41—C421.548 (5)
Fe2—C232.066 (4)C41—H41A0.99
Fe2—C242.055 (4)C41—H41B0.99
Fe2—C252.032 (4)C42—H42A0.99
Fe2—C262.035 (4)C42—H42B0.99
Fe2—C272.040 (4)C51—C521.546 (5)
Fe2—C282.044 (3)C51—H51A0.99
Fe2—C292.040 (4)C51—H51B0.99
Fe2—C2102.045 (4)C52—H52A0.99
C21—C221.436 (5)C52—H52B0.99
C12—C11—C15108.0 (3)C27—C28—H28125.9
C12—C11—C111125.2 (3)C28—C29—C210108.2 (4)
C15—C11—C111126.7 (4)C28—C29—H29125.9
C13—C12—C11108.1 (3)C210—C29—H29125.9
C13—C12—H12126.0C29—C210—C26107.6 (4)
C11—C12—H12126.0C29—C210—H210126.2
C12—C13—C14107.9 (3)C26—C210—H210126.2
C12—C13—H13126.1O22—C211—O21123.9 (3)
C14—C13—H13126.1O22—C211—C21122.0 (4)
C15—C14—C13108.5 (3)O21—C211—C21114.0 (3)
C15—C14—H14125.7C211—O21—H2110 (3)
C13—C14—H14125.7C41—N1—C31109.1 (3)
C14—C15—C11107.6 (3)C41—N1—C51109.0 (3)
C14—C15—H15126.2C31—N1—C51108.9 (3)
C11—C15—H15126.2C41—N1—H1106.9 (18)
C17—C16—C110108.7 (4)C31—N1—H1111.9 (19)
C17—C16—H16125.6C51—N1—H1111.0 (19)
C110—C16—H16125.6C32—N2—C42110.0 (3)
C18—C17—C16107.3 (4)C32—N2—C52108.6 (3)
C18—C17—H17126.3C42—N2—C52108.4 (3)
C16—C17—H17126.3N1—C31—C32109.8 (3)
C17—C18—C19108.6 (4)N1—C31—H31A109.7
C17—C18—H18125.7C32—C31—H31A109.7
C19—C18—H18125.7N1—C31—H31B109.7
C18—C19—C110107.9 (4)C32—C31—H31B109.7
C18—C19—H19126.0H31A—C31—H31B108.2
C110—C19—H19126.0N2—C32—C31109.9 (3)
C16—C110—C19107.3 (4)N2—C32—H32A109.7
C16—C110—H110126.3C31—C32—H32A109.7
C19—C110—H110126.3N2—C32—H32B109.7
O12—C111—O11124.0 (3)C31—C32—H32B109.7
O12—C111—C11121.8 (4)H32A—C32—H32B108.2
O11—C111—C11114.2 (3)N1—C41—C42110.2 (3)
C111—O11—H1106 (3)N1—C41—H41A109.6
C25—C21—C22107.7 (3)C42—C41—H41A109.6
C25—C21—C211124.3 (3)N1—C41—H41B109.6
C22—C21—C211127.9 (3)C42—C41—H41B109.6
C23—C22—C21107.5 (3)H41A—C41—H41B108.1
C23—C22—H22126.2N2—C42—C41109.3 (3)
C21—C22—H22126.2N2—C42—H42A109.8
C22—C23—C24108.7 (3)C41—C42—H42A109.8
C22—C23—H23125.6N2—C42—H42B109.8
C24—C23—H23125.6C41—C42—H42B109.8
C25—C24—C23108.0 (3)H42A—C42—H42B108.3
C25—C24—H24126.0N1—C51—C52110.0 (3)
C23—C24—H24126.0N1—C51—H51A109.7
C24—C25—C21108.0 (3)C52—C51—H51A109.7
C24—C25—H25126.0N1—C51—H51B109.7
C21—C25—H25126.0C52—C51—H51B109.7
C27—C26—C210108.3 (4)H51A—C51—H51B108.2
C27—C26—H26125.9N2—C52—C51109.3 (3)
C210—C26—H26125.9N2—C52—H52A109.8
C26—C27—C28107.6 (4)C51—C52—H52A109.8
C26—C27—H27126.2N2—C52—H52B109.8
C28—C27—H27126.2C51—C52—H52B109.8
C29—C28—C27108.2 (4)H52A—C52—H52B108.3
C29—C28—H28125.9
C12—C11—C111—O11175.8 (4)N1—C31—C32—N28.0 (5)
C12—C11—C111—O126.5 (7)C31—N1—C41—C4255.6 (4)
C15—C11—C111—O110.1 (6)C51—N1—C41—C4263.1 (4)
C15—C11—C111—O12177.8 (4)C32—N2—C42—C4162.1 (4)
C22—C21—C211—O213.2 (6)C52—N2—C42—C4156.4 (4)
C22—C21—C211—O22175.3 (4)N1—C41—C42—N26.2 (5)
C25—C21—C211—O21172.7 (4)C41—N1—C51—C5255.0 (4)
C25—C21—C211—O228.8 (7)C31—N1—C51—C5263.9 (4)
C41—N1—C31—C3263.8 (4)C32—N2—C52—C5155.1 (4)
C51—N1—C31—C3255.0 (5)C42—N2—C52—C5164.4 (4)
C42—N2—C32—C3154.3 (4)N1—C51—C52—N27.5 (4)
C52—N2—C32—C3164.2 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O11—H1···N11.06 (6)1.53 (5)2.578 (4)170 (5)
O21—H2···N20.99 (7)1.62 (7)2.604 (5)174 (6)
C13—H13···O22i0.952.513.401 (5)157
C42—H42A···O12ii0.992.443.327 (5)149
C52—H52B···O12ii0.992.493.369 (5)149
Symmetry codes: (i) x, y1/2, z+3/2; (ii) x, y+1, z+1.

Experimental details

Crystal data
Chemical formula[Fe(C5H5)(C6H5O2)]2·C6H12N2
Mr572.26
Crystal system, space groupMonoclinic, P21/c
Temperature (K)150
a, b, c (Å)11.3900 (2), 21.2256 (6), 11.7248 (3)
β (°) 118.2144 (12)
V3)2497.79 (10)
Z4
Radiation typeMo Kα
µ (mm1)1.20
Crystal size (mm)0.18 × 0.07 × 0.06
Data collection
DiffractometerKappa-CCD
diffractometer
Absorption correctionMulti-scan
(DENZO-SMN; Otwinowski & Minor, 1997)
Tmin, Tmax0.813, 0.932
No. of measured, independent and
observed [I > 2σ(I)] reflections
4527, 4385, 2722
Rint0.10
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.104, 0.99
No. of reflections4385
No. of parameters333
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.37, 0.44

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

Selected geometric parameters (Å, º) top
C111—O121.229 (4)C211—O221.220 (4)
C111—O111.320 (4)C211—O211.330 (4)
N1—C311.474 (5)N2—C321.477 (5)
N1—C411.471 (5)N2—C421.477 (4)
N1—C511.476 (5)N2—C521.487 (5)
C12—C11—C111—O11175.8 (4)N1—C31—C32—N28.0 (5)
C12—C11—C111—O126.5 (7)N1—C41—C42—N26.2 (5)
C22—C21—C211—O213.2 (6)N1—C51—C52—N27.5 (4)
C22—C21—C211—O22175.3 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O11—H1···N11.06 (6)1.53 (5)2.578 (4)170 (5)
O21—H2···N20.99 (7)1.62 (7)2.604 (5)174 (6)
C13—H13···O22i0.952.513.401 (5)157
C42—H42A···O12ii0.992.443.327 (5)149
C52—H52B···O12ii0.992.493.369 (5)149
Symmetry codes: (i) x, y1/2, z+3/2; (ii) x, y+1, z+1.
 

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