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In p-ferrocenylaniline, [Fe(C5H5)(C11H10N)], an easily synthesized alternative for ferrocenylamine, the orientation of the amine H atoms allows for conjugation of the nitro­gen lone pair with the π electrons of the benzene and cyclo­penta­dienyl rings. No hydrogen-bonding or π–π stacking inter­actions are present in the solid state.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680702764X/lh2417sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680702764X/lh2417Isup2.hkl
Contains datablock I

CCDC reference: 654738

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.044
  • wR factor = 0.095
  • Data-to-parameter ratio = 16.5

checkCIF/PLATON results

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Alert level C PLAT420_ALERT_2_C D-H Without Acceptor N1 - H1A ... ? PLAT420_ALERT_2_C D-H Without Acceptor N1 - H1B ... ?
Alert level G PLAT794_ALERT_5_G Check Predicted Bond Valency for Fe1 (3) 3.85
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check

Comment top

Ferrocene-containing dimers have received considerable interest over the years due to their potential applications in electrocatalysis (Togni & Hayashi, 1995; Sawamura & Ito, 1992; Nicolosi et al., 1994), ferromagnetism (Miller et al., 1996), chemical and biochemical sensing (Navarro et al., 2005; Brown et al., 2005; Okochi et al., 2005; Hickman et al., 1991) and self-assembled monolayer chemistry (Chidsey et al., 1990; Creager & Rowe, 1997). They are also of growing interest due to their unique structural, electrochemical and electronic structural properties. The production of dimeric ferrocenylamides has been hampered by the tedious synthesis of aminoferrocene, as it is difficult to produce in high enough yields to be useful in multi-step syntheses. In addition, the production of 1,1'-diaminoferrocene as the major product of most reaction pathways is a serious drawback. Although this compound can be purchased commercially, it is extremely expensive. Its phenyl derivative, the title compound p-ferrocenylaniline (I), on the other hand, can be easily produced in a two step synthesis from ferrocene by reaction with diazotated p-nitroaniline (Hu et al., 2001a), followed by the reduction of the resulting p-nitrophenylferrocene with Sn/HCl to produce the title compound p-ferrocenylaniline (Hu et al., 2001b). This paper presents the single-crystal structure of the title compound.

p-Ferrocenylaniline crystallizes in the orthorhombic space group Pbca with 8 molecules per unit cell (Figure 1). The conformation of the two Cp rings towards each other is close to eclipsed, and the substituted Cp and the phenyl ring are basically coplanar with a dihedral angle between the planes defined by C6 to C10 and C11 to C16 of 8.7 (2)°, a value not too different to that found for p-nitrophenylferrocene (13.5 (2)°, Zeller et al., 2004; see also: Roberts et al., 1988, Gallagher et al., 1997).

The hybridization of the amino group shows a tendency towards sp3 hybridization with angles between 114 and 117° (Table 1). The nitrogen atom is located slightly above the plane of the phenyl ring by 0.074 (3) Å. Together with the orientation of the amino hydrogen atoms, which are located below the phenyl plane by 0.11 (4) and 0.23 (4) Å, this allows for a conjugation of the nitrogen lone pair with the π electrons of the aromatic ring. This is in agreement with the 1H NMR spectral values, which are typical for ferrocenyl compounds with electron donating substituents: The cyclopentadienyl and phenyl protons have been shifted upfield from TMS, thus further conforming extensive π-overlap and electronic communication along the unsaturated backbone.

In contrast to aminoferrocene (Perrine et al., 2005) and also 1,1'-diaminoferrocene (Shafir et al., 2000), but similar to other structurally analyzed ferrocenyl amines (Rogers et al. 1998, Sunkel et al., 2000, Takaki et al., 1959) the title compound does not form hydrogen bonds in the solid state. Also no π-π stacking interactions are found in the structure: neighboring molecules are roughly perpendicular to each other with the C—H groups pointing towards the π-electrons of neighboring Cp and aromatic units (but at distances larger than the sum of the van-der-Waals radii). The packing and the lattice energy thus seems to be soley based on weak disperion interactions.

Related literature top

For the synthesis of p-ferrocenylaniline, see: Hu et al. (2001a,b). For related structures, see: Perrine et al. (2005); Shafir et al. (2000); Rogers et al. (1988); Sunkel et al. (2000); Takaki et al. (1959); Roberts et al. (1988); Gallagher et al. (1997); Zeller et al. (2004). For applications of ferrocene-containing dimers in electrocatalysis, see: Togni & Hayashi (1995); Sawamura & Ito (1992); Nicolosi et al. (1994); in ferromagnetism, see: Miller et al. (1988); in chemical and biochemical sensing, see: Navarro et al. (2005); Brown et al. (2005); Okochi et al. (2005); Hickman et al. (1991); and in self-assembled monolayer chemistry, see: Chidsey et al. (1990); Creager & Rowe (1997).

For related literature, see: Herbstein (2000); Rogers et al. (1988).

Experimental top

p-Nitrophenylferrocene was prepared by the method of Hu et al. (2001a). The crude product was purified using activated silica as the stationary phase and 95:5 hexanes:ethyl acetate as the eluent (yield 48%). 1H NMR (400 MHz, CDCl3): 4.067 (s, 5H, C5H5), 4.487 (pt, 2H, C5H4), 4.751 (pt, 2H, C5H4), 7.710 (d, 2H, C6H4), 8.150 (d, 2H, C6H4). MS: calculated for (M+) 307 m/z, found 307 m/z. p-Nitrophenylferrocene was also analyzed by single-crystal diffraction (Zeller et al., 2004) confirming the previously reported structure (Roberts et al., 1988, Gallagher et al., 1997). p-Ferrocenylaniline was prepared via the method of Hu et al. (2001b) from p-nitrophenylferrocene. The product was purified via column chromatography using activated silica as the stationary phase and 70:30 hexanes:ethyl acetate as the eluent (yield 88%). 1H NMR: 3.620 (s, 2H, NH2), 4.045 (s, 5H, C5H5), 4.249 (pt, 2H, C5H4), 4.552 (pt, 2H, C5H4), 6.651 (d, 2H, C6H4), 7.303 (d, 2H, C6H4). MS: calculated for (M+) 277 m/z, found 277 m/z.

X-ray quality single crystals of p-ferrocenylaniline were prepared via kinetically controlled solvent evaporation from 70:30 hexanes:ethyl acetate solutions to give yellow platelets.

Refinement top

Cp and aromatic H atoms were placed in calculated positions [C—H = 0.95 Å] and were refined with Uiso(H) = 1.2 Ueq(C) of the adjacent carbon atom. Amine hydrogen atom positions and isotropic displacement parameters were freely refined.

The s.u. values of the cell parameters are taken from the software recognizing that the values are unreasonably small (Herbstein, 2000).

Structure description top

Ferrocene-containing dimers have received considerable interest over the years due to their potential applications in electrocatalysis (Togni & Hayashi, 1995; Sawamura & Ito, 1992; Nicolosi et al., 1994), ferromagnetism (Miller et al., 1996), chemical and biochemical sensing (Navarro et al., 2005; Brown et al., 2005; Okochi et al., 2005; Hickman et al., 1991) and self-assembled monolayer chemistry (Chidsey et al., 1990; Creager & Rowe, 1997). They are also of growing interest due to their unique structural, electrochemical and electronic structural properties. The production of dimeric ferrocenylamides has been hampered by the tedious synthesis of aminoferrocene, as it is difficult to produce in high enough yields to be useful in multi-step syntheses. In addition, the production of 1,1'-diaminoferrocene as the major product of most reaction pathways is a serious drawback. Although this compound can be purchased commercially, it is extremely expensive. Its phenyl derivative, the title compound p-ferrocenylaniline (I), on the other hand, can be easily produced in a two step synthesis from ferrocene by reaction with diazotated p-nitroaniline (Hu et al., 2001a), followed by the reduction of the resulting p-nitrophenylferrocene with Sn/HCl to produce the title compound p-ferrocenylaniline (Hu et al., 2001b). This paper presents the single-crystal structure of the title compound.

p-Ferrocenylaniline crystallizes in the orthorhombic space group Pbca with 8 molecules per unit cell (Figure 1). The conformation of the two Cp rings towards each other is close to eclipsed, and the substituted Cp and the phenyl ring are basically coplanar with a dihedral angle between the planes defined by C6 to C10 and C11 to C16 of 8.7 (2)°, a value not too different to that found for p-nitrophenylferrocene (13.5 (2)°, Zeller et al., 2004; see also: Roberts et al., 1988, Gallagher et al., 1997).

The hybridization of the amino group shows a tendency towards sp3 hybridization with angles between 114 and 117° (Table 1). The nitrogen atom is located slightly above the plane of the phenyl ring by 0.074 (3) Å. Together with the orientation of the amino hydrogen atoms, which are located below the phenyl plane by 0.11 (4) and 0.23 (4) Å, this allows for a conjugation of the nitrogen lone pair with the π electrons of the aromatic ring. This is in agreement with the 1H NMR spectral values, which are typical for ferrocenyl compounds with electron donating substituents: The cyclopentadienyl and phenyl protons have been shifted upfield from TMS, thus further conforming extensive π-overlap and electronic communication along the unsaturated backbone.

In contrast to aminoferrocene (Perrine et al., 2005) and also 1,1'-diaminoferrocene (Shafir et al., 2000), but similar to other structurally analyzed ferrocenyl amines (Rogers et al. 1998, Sunkel et al., 2000, Takaki et al., 1959) the title compound does not form hydrogen bonds in the solid state. Also no π-π stacking interactions are found in the structure: neighboring molecules are roughly perpendicular to each other with the C—H groups pointing towards the π-electrons of neighboring Cp and aromatic units (but at distances larger than the sum of the van-der-Waals radii). The packing and the lattice energy thus seems to be soley based on weak disperion interactions.

For the synthesis of p-ferrocenylaniline, see: Hu et al. (2001a,b). For related structures, see: Perrine et al. (2005); Shafir et al. (2000); Rogers et al. (1988); Sunkel et al. (2000); Takaki et al. (1959); Roberts et al. (1988); Gallagher et al. (1997); Zeller et al. (2004). For applications of ferrocene-containing dimers in electrocatalysis, see: Togni & Hayashi (1995); Sawamura & Ito (1992); Nicolosi et al. (1994); in ferromagnetism, see: Miller et al. (1988); in chemical and biochemical sensing, see: Navarro et al. (2005); Brown et al. (2005); Okochi et al. (2005); Hickman et al. (1991); and in self-assembled monolayer chemistry, see: Chidsey et al. (1990); Creager & Rowe (1997).

For related literature, see: Herbstein (2000); Rogers et al. (1988).

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT-Plus (Bruker, 2003); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The molecular structure with the atomic numbering scheme. Thermal displacement parameters are at the 50% probabilty level, dotted lines represent the Fe-πCp bonds.
[Figure 2] Fig. 2. Scheme of the synthesis of I starting with ferrocene (Hu et al., 2001a,b).
p-Ferrocenylaniline top
Crystal data top
[Fe(C5H5)(C11H10N)]F(000) = 1152
Mr = 277.14Dx = 1.504 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 8682 reflections
a = 9.6762 (7) Åθ = 2.5–30.5°
b = 8.0284 (6) ŵ = 1.21 mm1
c = 31.515 (2) ÅT = 100 K
V = 2448.2 (3) Å3Plate, yellow
Z = 80.41 × 0.19 × 0.03 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
2821 independent reflections
Radiation source: fine-focus sealed tube2679 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.030
φ and ω scansθmax = 27.5°, θmin = 1.3°
Absorption correction: multi-scan
(SADABS in SAINT-Plus; Bruker, 2003)
h = 1212
Tmin = 0.712, Tmax = 0.960k = 1010
22095 measured reflectionsl = 4040
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: difference Fourier map
wR(F2) = 0.095H atoms treated by a mixture of independent and constrained refinement
S = 1.31 w = 1/[σ2(Fo2) + (0.0245P)2 + 5.1787P]
where P = (Fo2 + 2Fc2)/3
2821 reflections(Δ/σ)max = 0.001
171 parametersΔρmax = 0.57 e Å3
0 restraintsΔρmin = 0.34 e Å3
Crystal data top
[Fe(C5H5)(C11H10N)]V = 2448.2 (3) Å3
Mr = 277.14Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 9.6762 (7) ŵ = 1.21 mm1
b = 8.0284 (6) ÅT = 100 K
c = 31.515 (2) Å0.41 × 0.19 × 0.03 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
2821 independent reflections
Absorption correction: multi-scan
(SADABS in SAINT-Plus; Bruker, 2003)
2679 reflections with I > 2σ(I)
Tmin = 0.712, Tmax = 0.960Rint = 0.030
22095 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.095H atoms treated by a mixture of independent and constrained refinement
S = 1.31Δρmax = 0.57 e Å3
2821 reflectionsΔρmin = 0.34 e Å3
171 parameters
Special details top

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 F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.5396 (3)0.0175 (3)0.61108 (8)0.0200 (5)
H10.48750.06520.63360.024*
C20.6406 (3)0.1104 (3)0.61509 (8)0.0193 (5)
H20.66770.16320.64080.023*
C30.6937 (2)0.1451 (3)0.57415 (8)0.0191 (5)
H30.76290.22500.56760.023*
C40.6253 (2)0.0393 (3)0.54461 (8)0.0180 (5)
H40.64040.03640.51480.022*
C50.5305 (2)0.0611 (3)0.56757 (8)0.0185 (5)
H50.47110.14320.55580.022*
C60.4561 (2)0.4356 (3)0.57041 (7)0.0155 (5)
H60.52640.51810.57090.019*
C70.4063 (2)0.3527 (3)0.53379 (8)0.0164 (5)
H70.43710.37050.50550.020*
C80.3022 (2)0.2383 (3)0.54663 (7)0.0159 (5)
H80.25140.16620.52850.019*
C90.2876 (2)0.2508 (3)0.59135 (8)0.0150 (4)
H90.22530.18800.60830.018*
C100.3826 (2)0.3742 (3)0.60670 (8)0.0140 (4)
C110.3971 (2)0.4271 (3)0.65136 (7)0.0148 (5)
C120.3038 (3)0.3733 (3)0.68236 (8)0.0176 (5)
H120.23240.29790.67470.021*
C130.3132 (3)0.4273 (3)0.72402 (8)0.0207 (5)
H130.24850.38880.74440.025*
C140.4174 (3)0.5385 (3)0.73622 (8)0.0221 (5)
C150.5119 (3)0.5911 (3)0.70560 (8)0.0223 (5)
H150.58420.66520.71340.027*
C160.5018 (3)0.5370 (3)0.66416 (8)0.0194 (5)
H160.56720.57490.64390.023*
Fe10.48564 (3)0.18548 (4)0.575918 (10)0.01213 (11)
N10.4219 (3)0.5988 (4)0.77774 (8)0.0317 (6)
H1A0.495 (4)0.645 (5)0.7857 (12)0.034 (10)*
H1B0.384 (4)0.535 (5)0.7961 (12)0.041 (11)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0177 (11)0.0187 (12)0.0237 (13)0.0051 (10)0.0035 (10)0.0087 (10)
C20.0168 (11)0.0213 (12)0.0197 (12)0.0043 (10)0.0037 (9)0.0002 (10)
C30.0095 (10)0.0178 (11)0.0301 (14)0.0018 (9)0.0012 (9)0.0032 (10)
C40.0154 (11)0.0195 (12)0.0190 (12)0.0069 (9)0.0033 (9)0.0001 (10)
C50.0152 (11)0.0114 (10)0.0288 (13)0.0033 (9)0.0011 (9)0.0019 (10)
C60.0150 (11)0.0119 (10)0.0198 (12)0.0004 (9)0.0023 (9)0.0018 (9)
C70.0183 (11)0.0164 (11)0.0144 (11)0.0056 (9)0.0002 (9)0.0021 (9)
C80.0142 (10)0.0165 (11)0.0168 (11)0.0052 (9)0.0032 (9)0.0019 (9)
C90.0109 (10)0.0144 (10)0.0196 (11)0.0019 (9)0.0001 (9)0.0011 (9)
C100.0118 (10)0.0127 (10)0.0175 (11)0.0018 (9)0.0011 (9)0.0008 (9)
C110.0144 (11)0.0140 (11)0.0161 (11)0.0038 (9)0.0010 (9)0.0002 (9)
C120.0160 (11)0.0173 (11)0.0196 (12)0.0005 (9)0.0013 (9)0.0011 (10)
C130.0213 (12)0.0232 (12)0.0176 (12)0.0021 (10)0.0028 (10)0.0029 (10)
C140.0261 (13)0.0228 (13)0.0175 (12)0.0046 (11)0.0040 (10)0.0010 (10)
C150.0222 (12)0.0220 (13)0.0229 (13)0.0025 (11)0.0037 (10)0.0046 (10)
C160.0175 (11)0.0191 (12)0.0216 (12)0.0019 (10)0.0008 (9)0.0003 (10)
Fe10.00978 (17)0.01245 (17)0.01414 (17)0.00071 (12)0.00034 (12)0.00026 (13)
N10.0414 (15)0.0375 (15)0.0163 (11)0.0077 (12)0.0016 (11)0.0064 (11)
Geometric parameters (Å, º) top
C1—C51.418 (4)C8—C91.420 (3)
C1—C21.423 (4)C8—Fe12.045 (2)
C1—Fe12.039 (2)C8—H80.9500
C1—H10.9500C9—C101.435 (3)
C2—C31.417 (4)C9—Fe12.045 (2)
C2—Fe12.034 (2)C9—H90.9500
C2—H20.9500C10—C111.477 (3)
C3—C41.423 (4)C10—Fe12.057 (2)
C3—Fe12.040 (2)C11—C121.399 (3)
C3—H30.9500C11—C161.402 (3)
C4—C51.420 (3)C12—C131.386 (3)
C4—Fe12.044 (2)C12—H120.9500
C4—H40.9500C13—C141.400 (4)
C5—Fe12.043 (2)C13—H130.9500
C5—H50.9500C14—C151.395 (4)
C6—C71.417 (3)C14—N11.396 (3)
C6—C101.434 (3)C15—C161.380 (4)
C6—Fe12.036 (2)C15—H150.9500
C6—H60.9500C16—H160.9500
C7—C81.422 (3)N1—H1A0.84 (4)
C7—Fe12.038 (2)N1—H1B0.86 (4)
C7—H70.9500
C5—C1—C2107.8 (2)C13—C12—C11121.5 (2)
C5—C1—Fe169.84 (14)C13—C12—H12119.2
C2—C1—Fe169.36 (14)C11—C12—H12119.2
C5—C1—H1126.1C12—C13—C14120.5 (2)
C2—C1—H1126.1C12—C13—H13119.8
Fe1—C1—H1126.3C14—C13—H13119.8
C3—C2—C1108.1 (2)C15—C14—N1121.5 (3)
C3—C2—Fe169.88 (14)C15—C14—C13118.4 (2)
C1—C2—Fe169.73 (14)N1—C14—C13120.1 (3)
C3—C2—H2126.0C16—C15—C14120.8 (2)
C1—C2—H2126.0C16—C15—H15119.6
Fe1—C2—H2126.0C14—C15—H15119.6
C2—C3—C4108.0 (2)C15—C16—C11121.5 (2)
C2—C3—Fe169.42 (14)C15—C16—H16119.3
C4—C3—Fe169.74 (13)C11—C16—H16119.3
C2—C3—H3126.0C2—Fe1—C6116.61 (10)
C4—C3—H3126.0C2—Fe1—C7150.28 (11)
Fe1—C3—H3126.4C6—Fe1—C740.70 (9)
C5—C4—C3107.8 (2)C2—Fe1—C140.91 (10)
C5—C4—Fe169.66 (13)C6—Fe1—C1150.55 (10)
C3—C4—Fe169.46 (14)C7—Fe1—C1167.68 (11)
C5—C4—H4126.1C2—Fe1—C340.70 (10)
C3—C4—H4126.1C6—Fe1—C3107.04 (10)
Fe1—C4—H4126.4C7—Fe1—C3117.30 (10)
C1—C5—C4108.2 (2)C1—Fe1—C368.61 (10)
C1—C5—Fe169.51 (14)C2—Fe1—C568.56 (10)
C4—C5—Fe169.69 (14)C6—Fe1—C5167.00 (10)
C1—C5—H5125.9C7—Fe1—C5129.35 (10)
C4—C5—H5125.9C1—Fe1—C540.65 (10)
Fe1—C5—H5126.5C3—Fe1—C568.48 (10)
C7—C6—C10108.6 (2)C2—Fe1—C468.61 (10)
C7—C6—Fe169.75 (14)C6—Fe1—C4128.19 (10)
C10—C6—Fe170.29 (13)C7—Fe1—C4108.23 (10)
C7—C6—H6125.7C1—Fe1—C468.54 (10)
C10—C6—H6125.7C3—Fe1—C440.80 (10)
Fe1—C6—H6125.9C5—Fe1—C440.65 (10)
C6—C7—C8108.2 (2)C2—Fe1—C8167.25 (10)
C6—C7—Fe169.55 (13)C6—Fe1—C868.60 (10)
C8—C7—Fe169.89 (13)C7—Fe1—C840.76 (10)
C6—C7—H7125.9C1—Fe1—C8129.28 (10)
C8—C7—H7125.9C3—Fe1—C8151.31 (10)
Fe1—C7—H7126.3C5—Fe1—C8109.07 (10)
C9—C8—C7107.9 (2)C4—Fe1—C8118.36 (10)
C9—C8—Fe169.70 (13)C2—Fe1—C9128.50 (10)
C7—C8—Fe169.35 (13)C6—Fe1—C968.64 (10)
C9—C8—H8126.1C7—Fe1—C968.47 (10)
C7—C8—H8126.1C1—Fe1—C9108.39 (10)
Fe1—C8—H8126.5C3—Fe1—C9166.38 (10)
C8—C9—C10108.7 (2)C5—Fe1—C9118.54 (10)
C8—C9—Fe169.68 (13)C4—Fe1—C9151.82 (10)
C10—C9—Fe169.95 (13)C8—Fe1—C940.62 (9)
C8—C9—H9125.7C2—Fe1—C10106.83 (10)
C10—C9—H9125.7C6—Fe1—C1041.02 (9)
Fe1—C9—H9126.3C7—Fe1—C1068.87 (10)
C6—C10—C9106.6 (2)C1—Fe1—C10117.16 (10)
C6—C10—C11127.9 (2)C3—Fe1—C10127.48 (10)
C9—C10—C11125.5 (2)C5—Fe1—C10151.29 (10)
C6—C10—Fe168.69 (13)C4—Fe1—C10166.22 (10)
C9—C10—Fe169.09 (13)C8—Fe1—C1068.86 (9)
C11—C10—Fe1127.96 (17)C9—Fe1—C1040.96 (9)
C12—C11—C16117.4 (2)C14—N1—H1A117 (3)
C12—C11—C10121.0 (2)C14—N1—H1B114 (3)
C16—C11—C10121.6 (2)H1A—N1—H1B115 (4)

Experimental details

Crystal data
Chemical formula[Fe(C5H5)(C11H10N)]
Mr277.14
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)100
a, b, c (Å)9.6762 (7), 8.0284 (6), 31.515 (2)
V3)2448.2 (3)
Z8
Radiation typeMo Kα
µ (mm1)1.21
Crystal size (mm)0.41 × 0.19 × 0.03
Data collection
DiffractometerBruker SMART APEX CCD area-detector
Absorption correctionMulti-scan
(SADABS in SAINT-Plus; Bruker, 2003)
Tmin, Tmax0.712, 0.960
No. of measured, independent and
observed [I > 2σ(I)] reflections
22095, 2821, 2679
Rint0.030
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.095, 1.31
No. of reflections2821
No. of parameters171
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.57, 0.34

Computer programs: SMART (Bruker, 2002), SAINT-Plus (Bruker, 2003), SAINT-Plus, SHELXTL (Bruker, 2000), SHELXTL.

Selected geometric parameters (Å, º) top
C10—C111.477 (3)N1—H1A0.84 (4)
C14—N11.396 (3)N1—H1B0.86 (4)
C14—N1—H1A117 (3)H1A—N1—H1B115 (4)
C14—N1—H1B114 (3)
 

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