(Z)-3-Ferrocenyl-2-phenyl­acrylonitrile

Cao, L.-Y.; Ye, H.-Y.

doi:10.1107/S1600536808014517

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 6| June 2008| Page m822

doi:10.1107/S1600536808014517

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(Z)-3-Ferrocenyl-2-phenylacrylonitrile

Lu-Yang Cao ^a and Heng-Yun Ye ^a ^*

^aOrdered Matter Science Research Center, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China.
^*Correspondence e-mail: hyye@seu.edu.cn

(Received 6 May 2008; accepted 14 May 2008; online 17 May 2008)

In the structure of the title compound, [Fe(C₅H₅)(C₁₄H₁₀N)], the unsubstituted cyclopentadiene (Cp) ring is disordered over two positions, with site-occupancy factors 0.76 (2) and 0.24 (2). The dihedral angles between the substituted Cp ring and the major and the minor components of the disordered ring are 0.9 (5) and 6(2)°, repectively. The plane of the acrylonitrile unit makes dihedral angles of 6.1 (18) and 6.5 (4)° with the substituted Cp ring and the phenyl ring planes, respectively.

Related literature

For background to the chemistry of ferrocene, see: Long (1995 ); Roberto et al. (2000 ); Togni & Hayashi (1995 ). For the stuctures of ferrocene derivatives, see: Base et al. (2002 ); Hess et al. (1999 ). For bond distances in the acrylonitrile unit, see: Allen et al. (1987 ).

Experimental

Crystal data

[Fe(C₅H₅)(C₁₄H₁₀N)]
M_r = 313.17
Monoclinic, P 2₁ /c
a = 6.8255 (14) Å
b = 11.795 (2) Å
c = 19.939 (4) Å
β = 106.786 (16)°
V = 1536.8 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.97 mm⁻¹
T = 293 (2) K
0.18 × 0.06 × 0.05 mm

Data collection

Rigaku, SCXmini diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.892, T_max = 1.00 (expected range = 0.850–0.953)
15093 measured reflections
3523 independent reflections
2520 reflections with I > 2σ(I)
R_int = 0.050

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.126
S = 1.07
3523 reflections
206 parameters
30 restraints
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.40 e Å⁻³

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

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808014517/sj2497sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808014517/sj2497Isup2.hkl

checkCIF report

Comment top

The chemistry of ferrocene has received much attention because of its applications in many fields, such as in catalysis, organic or organometallic synthesis and materials (Togni, et al.(1995)). The use of ferrocene and its derivatives as non-linear optical(NLO) materials has also been reported (Long, 1995; Roberto et al., 2000). As part of our on going studies of the chemistry of ferrocene, we present here the structure of the title compound, (Z)-2-Phenyl-3-(ferrocenyl)acrylonitrile (I).

In I, the unsubstituted cyclopentadienyl (Cp) ring is disordered over two positions, the site occupancy factors are 0.76 (2) and 0.24 (2). The major disorder component is nearly parallel to the substituted Cp ring with a dihedral angle of 0.9 (5)° , and the rings are in an eclipsed configuration with the torsion angle C1-Cg1-Cg2-C10, -5.918 (3)°. The minor component of the disordered Cp ring is tilted slightly, making a dihedral of 6(2)° with C1···C5, and the rings are staggered, C1-Cg1-Cg2'-C9' 44.692 (4)° (Cg(1) denotes the centroid of the C1···C5 Cp ring, Cg(2) and Cg(2)' denote the centroids of the C6···C10 and C6'···C10' rings respectively). Fe-C distances to the substituted Cp ring vary from 2.030 (3) to 2.039 (3)Å, and are in the normal ranges (Hess et al., 1999; Base et al., 2002). Those to the unsubstituted Cp ring cover a wider range from 1.92 (3) to 2.084 (7) Å. The iron-ring centroid distances are Fe–Cg(1), 1.6378 (16) Å, Fe-Cg(2) 1.674 (3) Å and Fe–Cg(2)' 1.594 (13) Å. Within the acrylonitrile unit, bond angles and the C11═C12 double bond distance, 1.345 (3) Å) and C19≡N1 distances, 1.142 (4) Å, are normal (Allen et al. (1987). The plane of acrylonitrile unit makes dihedral angles of 6.13 ( 1.81 )° and 6.52 ( 0.39 )° with the C1···C5 ring and the C13···C18 phenyl ring plane, respectively.

Related literature top

For background to the chemistry of ferrocene, see: Long (1995); Roberto et al. (2000); Togni & Hayashi (1995). For the stuctures of ferrocene derivatives, see: Base et al. (2002); Hess et al. (1999). For bond distances and angles in the acrylonitrile unit, see: Allen et al. (1987).

Experimental top

To a mixture of ferrocenecarboxaldehyde and 2-phenyletonitrile in CH₂Cl₂ was added pyrrolidine and the mixture was heated to reflux temperature for 3 h. The reaction was cooled to room temperature and solvent removed. The crude product was purified by column chromatography on silica gel using ethyl acetate-petroleum ether (v:v, 1:3) as eluent to collect the main yellow band. Red crystals suitable for X-ray analysis were obtained by slow evaporation of a saturated solution of ethyl acetate-petroleum ether (v:v,1:3). BAND YELLOW, CRYSTALS RED. IS THIS CORRECT??

Computing details top

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

Figures top

Fig. 1. The structure of I showing the atom numbering scheme with displacement ellipsoids drawn at the 30% probability level. For clarity only atoms of the major disorder component of the unsubstituted cyclopentadiene ring are included.

(Z)-3-Ferrocenyl-2-phenylacrylonitrile top

Crystal data top

[Fe(C₅H₅)(C₁₄H₁₀N)]	F(000) = 648
M_r = 313.17	D_x = 1.354 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2947 reflections
a = 6.8255 (14) Å	θ = 3.1–27.5°
b = 11.795 (2) Å	µ = 0.97 mm⁻¹
c = 19.939 (4) Å	T = 293 K
β = 106.786 (16)°	Block, red
V = 1536.8 (5) Å³	0.18 × 0.06 × 0.05 mm
Z = 4

Data collection top

Rigaku, SCXmini diffractometer	3523 independent reflections
Radiation source: fine-focus sealed tube	2520 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.050
Detector resolution: 13.6612 pixels mm^-1	θ_max = 27.5°, θ_min = 3.1°
ω scans	h = −8→8
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −15→15
T_min = 0.892, T_max = 1.00	l = −25→25
15093 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.126	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0496P)² + 0.4337P] where P = (F_o² + 2F_c²)/3
3523 reflections	(Δ/σ)_max < 0.001
206 parameters	Δρ_max = 0.22 e Å⁻³
30 restraints	Δρ_min = −0.40 e Å⁻³

Crystal data top

[Fe(C₅H₅)(C₁₄H₁₀N)]	V = 1536.8 (5) Å³
M_r = 313.17	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 6.8255 (14) Å	µ = 0.97 mm⁻¹
b = 11.795 (2) Å	T = 293 K
c = 19.939 (4) Å	0.18 × 0.06 × 0.05 mm
β = 106.786 (16)°

Data collection top

Rigaku, SCXmini diffractometer	3523 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	2520 reflections with I > 2σ(I)
T_min = 0.892, T_max = 1.00	R_int = 0.050
15093 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	30 restraints
wR(F²) = 0.126	H-atom parameters constrained
S = 1.07	Δρ_max = 0.22 e Å⁻³
3523 reflections	Δρ_min = −0.40 e Å⁻³
206 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Fe1	0.27058 (7)	0.42653 (4)	0.29905 (2)	0.06096 (17)
N1	−0.4172 (4)	0.4888 (3)	0.12481 (18)	0.0911 (10)
C1	0.1205 (4)	0.3903 (2)	0.19717 (14)	0.0537 (6)
C2	0.2972 (5)	0.3198 (3)	0.22231 (17)	0.0701 (8)
H2A	0.4135	0.3160	0.2029	0.084*
C3	0.2759 (7)	0.2573 (3)	0.2800 (2)	0.0887 (11)
H3A	0.3752	0.2028	0.3077	0.106*
C4	0.0914 (7)	0.2867 (3)	0.2915 (2)	0.0922 (12)
H4A	0.0394	0.2566	0.3289	0.111*
C5	−0.0077 (5)	0.3694 (3)	0.24149 (17)	0.0714 (8)
H5A	−0.1400	0.4052	0.2377	0.086*
C6	0.2256 (9)	0.5813 (5)	0.3412 (3)	0.0813 (15)	0.764 (8)
H6A	0.0944	0.6208	0.3326	0.098*	0.764 (8)
C7	0.3062 (13)	0.4980 (6)	0.3956 (3)	0.105 (2)	0.764 (8)
H7A	0.2460	0.4729	0.4322	0.125*	0.764 (8)
C8	0.4978 (13)	0.4657 (7)	0.3864 (4)	0.113 (2)	0.764 (8)
H8A	0.5923	0.4107	0.4158	0.136*	0.764 (8)
C9	0.5340 (9)	0.5257 (7)	0.3301 (4)	0.0948 (17)	0.764 (8)
H9A	0.6548	0.5189	0.3133	0.114*	0.764 (8)
C10	0.3661 (11)	0.5945 (6)	0.3021 (4)	0.0794 (17)	0.764 (8)
H10A	0.3473	0.6441	0.2613	0.095*	0.764 (8)
C6'	0.270 (3)	0.5375 (19)	0.3729 (13)	0.0813 (15)	0.236 (8)
H6'A	0.1502	0.5559	0.3885	0.098*	0.236 (8)
C7'	0.421 (5)	0.452 (2)	0.4048 (12)	0.105 (2)	0.236 (8)
H7'A	0.4250	0.4022	0.4445	0.125*	0.236 (8)
C8'	0.562 (4)	0.457 (3)	0.3629 (14)	0.113 (2)	0.236 (8)
H8'A	0.6793	0.4061	0.3681	0.136*	0.236 (8)
C9'	0.488 (4)	0.534 (3)	0.3082 (11)	0.0948 (17)	0.236 (8)
H9'A	0.5544	0.5509	0.2718	0.114*	0.236 (8)
C10'	0.315 (4)	0.588 (3)	0.3162 (16)	0.0794 (17)	0.236 (8)
H10B	0.2395	0.6496	0.2872	0.095*	0.236 (8)
C11	0.1004 (4)	0.4723 (2)	0.14174 (13)	0.0480 (6)
H11A	0.2197	0.4875	0.1297	0.058*
C12	−0.0664 (4)	0.5297 (2)	0.10511 (13)	0.0452 (6)
C13	−0.0704 (4)	0.6196 (2)	0.05293 (13)	0.0483 (6)
C14	−0.2528 (5)	0.6672 (3)	0.01394 (16)	0.0699 (8)
H14A	−0.3752	0.6405	0.0197	0.084*
C15	−0.2574 (6)	0.7535 (3)	−0.03341 (19)	0.0869 (11)
H15A	−0.3820	0.7844	−0.0589	0.104*
C16	−0.0805 (7)	0.7933 (3)	−0.04285 (19)	0.0854 (11)
H16A	−0.0838	0.8524	−0.0740	0.103*
C17	0.1036 (6)	0.7462 (3)	−0.00626 (19)	0.0788 (10)
H17A	0.2244	0.7721	−0.0136	0.095*
C18	0.1093 (5)	0.6603 (3)	0.04146 (16)	0.0636 (7)
H18A	0.2345	0.6293	0.0663	0.076*
C19	−0.2607 (4)	0.5059 (2)	0.11687 (15)	0.0588 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe1	0.0733 (3)	0.0567 (3)	0.0496 (2)	−0.0014 (2)	0.0125 (2)	0.00379 (19)
N1	0.0504 (16)	0.114 (3)	0.110 (3)	−0.0086 (16)	0.0258 (16)	0.017 (2)
C1	0.0581 (16)	0.0510 (14)	0.0512 (15)	−0.0058 (13)	0.0147 (13)	−0.0008 (12)
C2	0.083 (2)	0.0592 (18)	0.0641 (18)	0.0146 (16)	0.0151 (16)	0.0034 (15)
C3	0.118 (3)	0.0534 (19)	0.082 (2)	0.005 (2)	0.009 (2)	0.0107 (17)
C4	0.115 (3)	0.081 (2)	0.077 (2)	−0.029 (2)	0.023 (2)	0.022 (2)
C5	0.0686 (19)	0.082 (2)	0.0657 (19)	−0.0166 (17)	0.0221 (16)	0.0088 (17)
C6	0.121 (4)	0.063 (3)	0.060 (3)	0.006 (3)	0.026 (3)	−0.005 (2)
C7	0.183 (7)	0.075 (4)	0.046 (3)	0.018 (4)	0.020 (4)	0.001 (2)
C8	0.133 (6)	0.107 (4)	0.068 (6)	0.021 (4)	−0.022 (3)	−0.021 (4)
C9	0.070 (4)	0.107 (4)	0.085 (5)	−0.015 (3)	−0.013 (3)	−0.019 (4)
C10	0.089 (5)	0.066 (2)	0.082 (4)	−0.019 (3)	0.023 (3)	−0.008 (2)
C6'	0.121 (4)	0.063 (3)	0.060 (3)	0.006 (3)	0.026 (3)	−0.005 (2)
C7'	0.183 (7)	0.075 (4)	0.046 (3)	0.018 (4)	0.020 (4)	0.001 (2)
C8'	0.133 (6)	0.107 (4)	0.068 (6)	0.021 (4)	−0.022 (3)	−0.021 (4)
C9'	0.070 (4)	0.107 (4)	0.085 (5)	−0.015 (3)	−0.013 (3)	−0.019 (4)
C10'	0.089 (5)	0.066 (2)	0.082 (4)	−0.019 (3)	0.023 (3)	−0.008 (2)
C11	0.0455 (14)	0.0553 (14)	0.0461 (14)	0.0003 (12)	0.0177 (11)	−0.0021 (12)
C12	0.0406 (13)	0.0525 (14)	0.0433 (13)	−0.0017 (11)	0.0135 (11)	−0.0073 (11)
C13	0.0522 (14)	0.0519 (14)	0.0394 (13)	0.0001 (12)	0.0108 (11)	−0.0072 (11)
C14	0.0583 (17)	0.088 (2)	0.0609 (18)	0.0090 (16)	0.0133 (15)	0.0151 (16)
C15	0.082 (2)	0.102 (3)	0.069 (2)	0.023 (2)	0.0105 (19)	0.025 (2)
C16	0.114 (3)	0.076 (2)	0.065 (2)	0.004 (2)	0.025 (2)	0.0182 (18)
C17	0.082 (2)	0.078 (2)	0.077 (2)	−0.0134 (19)	0.0245 (19)	0.0116 (18)
C18	0.0584 (17)	0.0674 (19)	0.0616 (18)	−0.0044 (15)	0.0119 (14)	0.0060 (15)
C19	0.0492 (16)	0.0637 (17)	0.0605 (17)	−0.0033 (14)	0.0112 (13)	0.0009 (14)

Geometric parameters (Å, º) top

Fe1—C9'	1.92 (3)	C8—H8A	0.9800
Fe1—C10'	1.94 (3)	C9—C10	1.383 (7)
Fe1—C6'	1.970 (19)	C9—H9A	0.9800
Fe1—C8	2.023 (7)	C10—H10A	0.9800
Fe1—C5	2.029 (3)	C6'—C10'	1.388 (17)
Fe1—C2	2.030 (3)	C6'—C7'	1.451 (18)
Fe1—C4	2.032 (4)	C6'—H6'A	0.9800
Fe1—C3	2.034 (4)	C7'—C8'	1.445 (19)
Fe1—C1	2.039 (3)	C7'—H7'A	0.9800
Fe1—C7	2.051 (5)	C8'—C9'	1.396 (18)
Fe1—C8'	2.06 (3)	C8'—H8'A	0.9800
Fe1—C6	2.069 (5)	C9'—C10'	1.393 (17)
N1—C19	1.142 (4)	C9'—H9'A	0.9800
C1—C2	1.431 (4)	C10'—H10B	0.9800
C1—C5	1.433 (4)	C11—C12	1.345 (3)
C1—C11	1.445 (4)	C11—H11A	0.9300
C2—C3	1.409 (5)	C12—C19	1.439 (4)
C2—H2A	0.9800	C12—C13	1.480 (4)
C3—C4	1.387 (5)	C13—C14	1.382 (4)
C3—H3A	0.9800	C13—C18	1.396 (4)
C4—C5	1.419 (5)	C14—C15	1.383 (5)
C4—H4A	0.9800	C14—H14A	0.9300
C5—H5A	0.9800	C15—C16	1.359 (5)
C6—C10	1.408 (8)	C15—H15A	0.9300
C6—C7	1.449 (7)	C16—C17	1.375 (5)
C6—H6A	0.9800	C16—H16A	0.9300
C7—C8	1.424 (10)	C17—C18	1.382 (4)
C7—H7A	0.9800	C17—H17A	0.9300
C8—C9	1.408 (10)	C18—H18A	0.9300

C9'—Fe1—C10'	42.3 (7)	C4—C5—Fe1	69.7 (2)
C9'—Fe1—C6'	70.2 (8)	C1—C5—Fe1	69.73 (17)
C10'—Fe1—C6'	41.5 (6)	C4—C5—H5A	126.3
C9'—Fe1—C8	52.3 (7)	C1—C5—H5A	126.3
C10'—Fe1—C8	65.3 (9)	Fe1—C5—H5A	126.3
C6'—Fe1—C8	51.1 (7)	C10—C6—C7	108.5 (5)
C9'—Fe1—C5	147.7 (7)	C10—C6—Fe1	70.6 (4)
C10'—Fe1—C5	119.9 (8)	C7—C6—Fe1	68.8 (3)
C6'—Fe1—C5	116.1 (6)	C10—C6—H6A	125.7
C8—Fe1—C5	157.2 (3)	C7—C6—H6A	125.7
C9'—Fe1—C2	104.1 (8)	Fe1—C6—H6A	125.7
C10'—Fe1—C2	134.2 (8)	C8—C7—C6	104.4 (6)
C6'—Fe1—C2	174.3 (6)	C8—C7—Fe1	68.5 (3)
C8—Fe1—C2	125.3 (3)	C6—C7—Fe1	70.1 (3)
C5—Fe1—C2	68.93 (14)	C8—C7—H7A	127.8
C9'—Fe1—C4	166.9 (9)	C6—C7—H7A	127.8
C10'—Fe1—C4	150.3 (8)	Fe1—C7—H7A	127.8
C6'—Fe1—C4	117.6 (7)	C9—C8—C7	110.3 (7)
C8—Fe1—C4	123.0 (3)	C9—C8—Fe1	72.3 (4)
C5—Fe1—C4	40.89 (14)	C7—C8—Fe1	70.6 (4)
C2—Fe1—C4	67.89 (17)	C9—C8—H8A	124.8
C9'—Fe1—C3	127.5 (9)	C7—C8—H8A	124.8
C10'—Fe1—C3	169.8 (8)	Fe1—C8—H8A	124.8
C6'—Fe1—C3	142.7 (8)	C10—C9—C8	107.5 (6)
C8—Fe1—C3	109.5 (3)	C10—C9—Fe1	70.5 (4)
C5—Fe1—C3	68.47 (16)	C8—C9—Fe1	67.7 (4)
C2—Fe1—C3	40.58 (14)	C10—C9—H9A	126.2
C4—Fe1—C3	39.89 (15)	C8—C9—H9A	126.2
C9'—Fe1—C1	112.6 (6)	Fe1—C9—H9A	126.2
C10'—Fe1—C1	112.9 (8)	C9—C10—C6	109.2 (5)
C6'—Fe1—C1	140.8 (8)	C9—C10—Fe1	70.7 (4)
C8—Fe1—C1	161.0 (3)	C6—C10—Fe1	69.7 (3)
C5—Fe1—C1	41.24 (12)	C9—C10—H10A	125.4
C2—Fe1—C1	41.19 (12)	C6—C10—H10A	125.4
C4—Fe1—C1	68.75 (13)	Fe1—C10—H10A	125.4
C3—Fe1—C1	68.87 (13)	C10'—C6'—C7'	110.9 (15)
C9'—Fe1—C7	76.2 (7)	C10'—C6'—Fe1	68.1 (16)
C10'—Fe1—C7	57.4 (8)	C7'—C6'—Fe1	73.2 (14)
C6'—Fe1—C7	18.4 (6)	C10'—C6'—H6'A	124.6
C8—Fe1—C7	40.9 (3)	C7'—C6'—H6'A	124.6
C5—Fe1—C7	120.3 (3)	Fe1—C6'—H6'A	124.6
C2—Fe1—C7	161.9 (3)	C8'—C7'—C6'	103.2 (14)
C4—Fe1—C7	108.0 (2)	C8'—C7'—Fe1	68.6 (16)
C3—Fe1—C7	125.1 (2)	C6'—C7'—Fe1	64.9 (13)
C1—Fe1—C7	155.6 (3)	C8'—C7'—H7'A	128.4
C9'—Fe1—C8'	40.9 (6)	C6'—C7'—H7'A	128.4
C10'—Fe1—C8'	69.4 (9)	Fe1—C7'—H7'A	128.4
C6'—Fe1—C8'	68.5 (8)	C9'—C8'—C7'	109.1 (16)
C8—Fe1—C8'	20.8 (6)	C9'—C8'—Fe1	64.2 (15)
C5—Fe1—C8'	170.4 (8)	C7'—C8'—Fe1	70.5 (16)
C2—Fe1—C8'	107.0 (7)	C9'—C8'—H8'A	125.2
C4—Fe1—C8'	129.7 (8)	C7'—C8'—H8'A	125.2
C3—Fe1—C8'	102.6 (8)	Fe1—C8'—H8'A	125.2
C1—Fe1—C8'	140.3 (7)	C10'—C9'—C8'	109.5 (16)
C7—Fe1—C8'	61.1 (7)	C10'—C9'—Fe1	69.7 (17)
C9'—Fe1—C6	65.3 (9)	C8'—C9'—Fe1	74.9 (16)
C10'—Fe1—C6	25.6 (7)	C10'—C9'—H9'A	125.2
C6'—Fe1—C6	22.8 (6)	C8'—C9'—H9'A	125.2
C8—Fe1—C6	67.4 (3)	Fe1—C9'—H9'A	125.2
C5—Fe1—C6	107.3 (2)	C6'—C10'—C9'	107.1 (15)
C2—Fe1—C6	155.4 (2)	C6'—C10'—Fe1	70.3 (14)
C4—Fe1—C6	126.1 (2)	C9'—C10'—Fe1	68.0 (17)
C3—Fe1—C6	162.6 (2)	C6'—C10'—H10B	126.5
C1—Fe1—C6	119.9 (2)	C9'—C10'—H10B	126.5
C7—Fe1—C6	41.2 (2)	Fe1—C10'—H10B	126.5
C8'—Fe1—C6	80.0 (7)	C12—C11—C1	129.1 (2)
C2—C1—C5	106.7 (3)	C12—C11—H11A	115.4
C2—C1—C11	122.8 (3)	C1—C11—H11A	115.4
C5—C1—C11	130.3 (3)	C11—C12—C19	119.3 (2)
C2—C1—Fe1	69.07 (17)	C11—C12—C13	125.7 (2)
C5—C1—Fe1	69.03 (17)	C19—C12—C13	115.0 (2)
C11—C1—Fe1	122.09 (19)	C14—C13—C18	117.4 (3)
C3—C2—C1	108.4 (3)	C14—C13—C12	121.1 (2)
C3—C2—Fe1	69.9 (2)	C18—C13—C12	121.5 (2)
C1—C2—Fe1	69.74 (17)	C13—C14—C15	121.5 (3)
C3—C2—H2A	125.8	C13—C14—H14A	119.3
C1—C2—H2A	125.8	C15—C14—H14A	119.3
Fe1—C2—H2A	125.8	C16—C15—C14	120.2 (3)
C4—C3—C2	108.4 (3)	C16—C15—H15A	119.9
C4—C3—Fe1	70.0 (2)	C14—C15—H15A	119.9
C2—C3—Fe1	69.55 (19)	C15—C16—C17	120.0 (3)
C4—C3—H3A	125.8	C15—C16—H16A	120.0
C2—C3—H3A	125.8	C17—C16—H16A	120.0
Fe1—C3—H3A	125.8	C16—C17—C18	120.1 (3)
C3—C4—C5	109.1 (3)	C16—C17—H17A	120.0
C3—C4—Fe1	70.1 (2)	C18—C17—H17A	120.0
C5—C4—Fe1	69.45 (19)	C17—C18—C13	120.9 (3)
C3—C4—H4A	125.4	C17—C18—H18A	119.6
C5—C4—H4A	125.4	C13—C18—H18A	119.6
Fe1—C4—H4A	125.4	N1—C19—C12	178.3 (3)
C4—C5—C1	107.4 (3)

Experimental details

Crystal data
Chemical formula	[Fe(C₅H₅)(C₁₄H₁₀N)]
M_r	313.17
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	6.8255 (14), 11.795 (2), 19.939 (4)
β (°)	106.786 (16)
V (Å³)	1536.8 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.97
Crystal size (mm)	0.18 × 0.06 × 0.05

Data collection
Diffractometer	Rigaku, SCXmini diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.892, 1.00
No. of measured, independent and observed [I > 2σ(I)] reflections	15093, 3523, 2520
R_int	0.050
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.126, 1.07
No. of reflections	3523
No. of parameters	206
No. of restraints	30
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.40

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick,2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

This work was supported by a start-up grant from Southeast University to Professor Ren-Gen Xiong.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–S19. CrossRef Web of Science Google Scholar
Base, T., Cisarova, I. & Stepnicka, P. (2002). Inorg. Chem. Commun. 5, 46–50. Web of Science CSD CrossRef CAS Google Scholar
Hess, A., Brosch, O., Weyhermuller, T. & Metzler-Nolte, N. (1999). J. Organomet. Chem. 589, 75–84. Web of Science CSD CrossRef CAS Google Scholar
Long, N. J. (1995). Angew. Chem. Int. Ed. Engl. 34, 21–75. CrossRef CAS Web of Science Google Scholar
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Roberto, D., Ugo, R., Cariati, S. B. E. & Cariati, F. (2000). Organometallics, 19, 1775–1788. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Togni, A. & Hayashi, T. (1995). Editors. Ferrocenes. Weinheim: VCH. Google Scholar