(Z)-3-Ferrocenyl-2-(3-pyrid­yl)­acrylo­nitrile

Chen, F.; Ye, H.-Y.

doi:10.1107/S1600536808025531

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 9| September 2008| Page m1165

doi:10.1107/S1600536808025531

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(Z)-3-Ferrocenyl-2-(3-pyridyl)acrylonitrile

Fang Chen ^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 4 June 2008; accepted 8 August 2008; online 16 August 2008)

The molecular structure of the title compound, [Fe(C₅H₅)(C₁₃H₉N₂)], (I), is analogous to that of the compound (Z)-3-ferrocenyl-2-phenylacrylonitrile [Cao & Ye (2008). Acta Cryst. E64, m822], (II), with the pyridine ring in (I) replacing the benzene ring in (II). While the corresponding bond distances and angles in the two compounds show no significant differences, the two dihedral angles between the planes through the acrylonitrile group and the two rings attached to it (substituted Cp and pyridine) of 16.8 (4) and 20.1 (4)° in (I) are different from the corresponding dihedral angles [19.6 (3) and 6.5 (4)°] in (II). The unsubstituted ring is disordered over two positions, with site-occupancy factors of 0.70 (1) and 0.30 (1). The major and minor components of the disordered ring are almost coplanar and are also parallel to the substituted cyclopentadiene ring plane, with a dihedral angle of 0.3 (6)°.

Related literature

For background to the chemistry of ferrocene, see: Long (1995 ); Roberto et al. (2000 ); Togni & Hayashi (1995 ). For the structure of an analogous compound, see: Cao & Ye (2008 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

[Fe(C₅H₅)(C₁₃H₉N₂)]
M_r = 314.16
Monoclinic, P 2₁ /c
a = 11.552 (3) Å
b = 9.2557 (15) Å
c = 14.458 (5) Å
β = 111.679 (15)°
V = 1436.6 (7) Å³
Z = 4
Mo Kα radiation
μ = 1.04 mm⁻¹
T = 293 (2) K
0.25 × 0.2 × 0.1 mm

Data collection

Rigaku SCXmini diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.896, T_max = 1.000 (expected range = 0.808–0.901)
14447 measured reflections
3290 independent reflections
2008 reflections with I > 2σ(I)
R_int = 0.084

Refinement

R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.107
S = 0.99
3290 reflections
206 parameters
22 restraints
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.27 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/S1600536808025531/ez2133sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808025531/ez2133Isup2.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 design (Togni & Hayashi, 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 into the chemistry of ferrocene, we report the crystal structure of the title compound (I), Fig. 1.

I is analogous to the compound (Z)-2-Phenyl-3-(ferrocenyl)acrylonitrile (II) (Cao & Ye, 2008), except for the replacement of the benzene ring in II by the pyridine ring in I. The two molecular structures show no significant differences between the corresponding bond distances and angles. Although the two compounds have the same spacegroup (P 2₁/c) their crystal structures are obviously different, since the unit cell parameters differ. This is because the two dihedral angles between the planes through the acrylonitrile group and the two attached rings (the substituted Cp ring, C1–C5, and the pyridine ring, C13–C18) [16.8 (4)°, 20.1 (4)°] in I are different from the corresponding dihedral angles [6(2)°, 6.5 (4)°] in II. The unsubstituted Cp ring is disordered over two positions, with site occupancy factors 0.70 (1) and 0.30 (1). The major (C6–C10) and the minor (C6'–C10') components of the disordered ring are almost coplanar with mean deviations of 0.0239 Å from the planes. Both disordered rings are parallel to the C1–C5 ring plane with dihedral angles of 0.3 (6)°. The major component is in an eclipsed configuration relative to the substituted Cp ring with a C1-Cg1-Cg2-C10 torsion angle of -0.2 (4)°; while the minor component is staggered, with a C1-Cg1-Cg2-C10' torsion angle of 24 (2)° [Cg(1) denotes the centroid of the substituted Cp ligand; Cg(2) denotes the centroid of the unsubstituted Cp ligand]. The iron-ring centroid distances are Fe—Cg(1), 1.638 (2) Å; Fe—Cg(2), 1.6282 (5) Å. Within the acrylonitrile unit, bond distances and angles are normal (Allen et al., 1987).

Related literature top

For background to the chemistry of ferrocene, see: Long (1995); Roberto et al. (2000); Togni & Hayashi (1995). For the structure of an analogous compound, see: Cao & Ye (2008). For bond-length data, see: Allen et al. (1987).

Experimental top

The title compound was prepared by an analogous procedure to that for (Z)-2-Phenyl-3-(ferrocenyl)acrylonitrile (Cao & Ye, 2008). Red crystals suitable for X-ray analysis were obtained by slow evaporation of a saturated ethyl ether solution.

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-(3-pyridyl)acrylonitrile top

Crystal data top

[Fe(C₅H₅)(C₁₃H₉N₂)]	F(000) = 648
M_r = 314.16	D_x = 1.453 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2602 reflections
a = 11.552 (3) Å	θ = 2.7–27.5°
b = 9.2557 (15) Å	µ = 1.04 mm⁻¹
c = 14.458 (5) Å	T = 293 K
β = 111.679 (15)°	Block, red
V = 1436.6 (7) Å³	0.25 × 0.2 × 0.1 mm
Z = 4

Data collection top

Rigaku SCXmini diffractometer	3290 independent reflections
Radiation source: fine-focus sealed tube	2008 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.084
Detector resolution: 13.6612 pixels mm^-1	θ_max = 27.5°, θ_min = 2.7°
ω scans	h = −14→14
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −12→12
T_min = 0.896, T_max = 1.000	l = −18→18
14447 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) = 0.107	H-atom parameters constrained
S = 0.99	w = 1/[σ²(F_o²) + (0.0415P)²] where P = (F_o² + 2F_c²)/3
3290 reflections	(Δ/σ)_max = 0.006
206 parameters	Δρ_max = 0.24 e Å⁻³
22 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

[Fe(C₅H₅)(C₁₃H₉N₂)]	V = 1436.6 (7) Å³
M_r = 314.16	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.552 (3) Å	µ = 1.04 mm⁻¹
b = 9.2557 (15) Å	T = 293 K
c = 14.458 (5) Å	0.25 × 0.2 × 0.1 mm
β = 111.679 (15)°

Data collection top

Rigaku SCXmini diffractometer	3290 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	2008 reflections with I > 2σ(I)
T_min = 0.896, T_max = 1.000	R_int = 0.084
14447 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	22 restraints
wR(F²) = 0.107	H-atom parameters constrained
S = 0.99	Δρ_max = 0.24 e Å⁻³
3290 reflections	Δρ_min = −0.27 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 > 2sigma(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	0.23682 (4)	0.84541 (5)	0.05742 (3)	0.04190 (16)
C1	0.2053 (3)	0.6292 (3)	0.0517 (2)	0.0394 (8)
C2	0.3166 (3)	0.6649 (4)	0.1352 (2)	0.0467 (8)
H2	0.3963	0.6306	0.1463	0.056*
C3	0.2840 (3)	0.7601 (4)	0.1970 (3)	0.0546 (9)
H3	0.3391	0.7994	0.2560	0.065*
C4	0.1550 (4)	0.7868 (4)	0.1557 (3)	0.0541 (9)
H4	0.1103	0.8459	0.1826	0.065*
C5	0.1059 (3)	0.7077 (3)	0.0662 (3)	0.0470 (8)
H5	0.0227	0.7064	0.0236	0.056*
C6	0.3482 (8)	0.9264 (10)	−0.0106 (9)	0.071 (2)	0.699 (7)
H6	0.4200	0.8829	−0.0120	0.085*	0.699 (7)
C7	0.3419 (10)	1.0228 (12)	0.0626 (9)	0.077 (2)	0.699 (7)
H7	0.4092	1.0545	0.1174	0.092*	0.699 (7)
C8	0.2160 (10)	1.0636 (7)	0.0390 (7)	0.0603 (19)	0.699 (7)
H8	0.1857	1.1252	0.0756	0.072*	0.699 (7)
C9	0.1453 (6)	0.9930 (9)	−0.0507 (6)	0.0509 (16)	0.699 (7)
H9	0.0597	1.0014	−0.0840	0.061*	0.699 (7)
C10	0.2262 (10)	0.9071 (8)	−0.0817 (5)	0.0542 (18)	0.699 (7)
H10	0.2033	0.8490	−0.1381	0.065*	0.699 (7)
C10'	0.303 (3)	0.904 (2)	−0.0488 (16)	0.0542 (18)	0.301 (7)
H10'	0.3310	0.8412	−0.0860	0.065*	0.301 (7)
C9'	0.1810 (19)	0.950 (2)	−0.0742 (13)	0.0509 (16)	0.301 (7)
H9'	0.1135	0.9227	−0.1304	0.061*	0.301 (7)
C8'	0.178 (2)	1.039 (2)	−0.0049 (18)	0.0603 (19)	0.301 (7)
H8'	0.1062	1.0863	−0.0065	0.072*	0.301 (7)
C7'	0.298 (3)	1.056 (3)	0.075 (2)	0.077 (2)	0.301 (7)
H7'	0.3194	1.1108	0.1326	0.092*	0.301 (7)
C6'	0.377 (2)	0.967 (3)	0.041 (2)	0.071 (2)	0.301 (7)
H6'	0.4620	0.9543	0.0730	0.085*	0.301 (7)
C11	0.1881 (3)	0.5403 (3)	−0.0341 (2)	0.0403 (8)
H11A	0.1145	0.5558	−0.0882	0.048*
C12	0.2634 (3)	0.4379 (3)	−0.0470 (2)	0.0381 (7)
C13	0.2356 (3)	0.3444 (3)	−0.1358 (2)	0.0396 (7)
C14	0.3280 (3)	0.2680 (4)	−0.1533 (3)	0.0576 (10)
H14A	0.4108	0.2790	−0.1112	0.069*
C15	0.2968 (4)	0.1755 (4)	−0.2333 (3)	0.0660 (11)
H15A	0.3581	0.1237	−0.2463	0.079*
C16	0.1742 (4)	0.1610 (4)	−0.2935 (3)	0.0642 (11)
H16A	0.1539	0.0978	−0.3471	0.077*
C18	0.1149 (3)	0.3232 (4)	−0.2021 (3)	0.0547 (9)
H18A	0.0517	0.3756	−0.1922	0.066*
C19	0.3819 (3)	0.4094 (4)	0.0320 (3)	0.0484 (9)
N1	0.4752 (3)	0.3827 (4)	0.0921 (2)	0.0740 (10)
N17	0.0830 (3)	0.2324 (4)	−0.2791 (2)	0.0676 (9)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe1	0.0474 (3)	0.0360 (3)	0.0422 (3)	−0.0029 (2)	0.0163 (2)	0.0004 (2)
C1	0.0403 (18)	0.0351 (19)	0.0415 (18)	−0.0043 (14)	0.0137 (16)	0.0013 (14)
C2	0.0431 (19)	0.045 (2)	0.0422 (18)	−0.0018 (16)	0.0043 (16)	0.0055 (16)
C3	0.069 (3)	0.053 (2)	0.0353 (18)	−0.010 (2)	0.0118 (19)	0.0001 (17)
C4	0.066 (3)	0.056 (2)	0.048 (2)	−0.0045 (19)	0.029 (2)	−0.0031 (17)
C5	0.045 (2)	0.049 (2)	0.048 (2)	−0.0048 (16)	0.0181 (17)	−0.0001 (16)
C6	0.060 (4)	0.069 (6)	0.089 (7)	−0.006 (4)	0.033 (4)	0.026 (5)
C7	0.082 (7)	0.056 (7)	0.079 (5)	−0.027 (5)	0.015 (5)	0.003 (3)
C8	0.096 (6)	0.028 (3)	0.052 (5)	0.002 (3)	0.021 (4)	−0.007 (3)
C9	0.065 (4)	0.041 (4)	0.050 (4)	0.014 (3)	0.024 (3)	0.004 (3)
C10	0.074 (5)	0.049 (3)	0.053 (4)	0.017 (4)	0.039 (4)	0.016 (3)
C10'	0.074 (5)	0.049 (3)	0.053 (4)	0.017 (4)	0.039 (4)	0.016 (3)
C9'	0.065 (4)	0.041 (4)	0.050 (4)	0.014 (3)	0.024 (3)	0.004 (3)
C8'	0.096 (6)	0.028 (3)	0.052 (5)	0.002 (3)	0.021 (4)	−0.007 (3)
C7'	0.082 (7)	0.056 (7)	0.079 (5)	−0.027 (5)	0.015 (5)	0.003 (3)
C6'	0.060 (4)	0.069 (6)	0.089 (7)	−0.006 (4)	0.033 (4)	0.026 (5)
C11	0.0376 (18)	0.0352 (18)	0.0442 (19)	−0.0051 (14)	0.0104 (16)	0.0011 (14)
C12	0.0364 (17)	0.0347 (18)	0.0397 (18)	−0.0016 (15)	0.0100 (15)	0.0035 (14)
C13	0.0426 (18)	0.0365 (18)	0.0412 (17)	0.0005 (15)	0.0174 (16)	0.0062 (15)
C14	0.050 (2)	0.063 (3)	0.060 (2)	0.0082 (19)	0.019 (2)	−0.002 (2)
C15	0.081 (3)	0.065 (3)	0.059 (2)	0.022 (2)	0.034 (2)	0.000 (2)
C16	0.089 (3)	0.056 (2)	0.048 (2)	0.006 (2)	0.025 (2)	−0.0055 (19)
C18	0.052 (2)	0.062 (3)	0.049 (2)	0.0017 (18)	0.0176 (19)	−0.0116 (18)
C19	0.053 (2)	0.040 (2)	0.051 (2)	0.0033 (17)	0.018 (2)	0.0017 (16)
N1	0.057 (2)	0.080 (3)	0.064 (2)	0.0226 (18)	−0.0024 (18)	0.0045 (18)
N17	0.068 (2)	0.072 (2)	0.056 (2)	0.0028 (18)	0.0149 (18)	−0.0192 (17)

Geometric parameters (Å, º) top

Fe1—C8'	2.009 (18)	C9—C10	1.420 (8)
Fe1—C9'	2.018 (15)	C9—H9	0.9300
Fe1—C5	2.018 (3)	C10—H10	0.9300
Fe1—C7	2.026 (10)	C10'—C9'	1.38 (2)
Fe1—C10'	2.026 (18)	C10'—C6'	1.39 (3)
Fe1—C6	2.029 (8)	C10'—H10'	0.9300
Fe1—C1	2.030 (3)	C9'—C8'	1.31 (2)
Fe1—C2	2.035 (3)	C9'—H9'	0.9300
Fe1—C8	2.040 (6)	C8'—C7'	1.45 (3)
Fe1—C3	2.045 (3)	C8'—H8'	0.9300
Fe1—C4	2.049 (3)	C7'—C6'	1.44 (3)
Fe1—C10	2.050 (6)	C7'—H7'	0.9300
C1—C5	1.439 (4)	C6'—H6'	0.9300
C1—C11	1.440 (4)	C11—C12	1.345 (4)
C1—C2	1.440 (4)	C11—H11A	0.9300
C2—C3	1.401 (5)	C12—C19	1.446 (5)
C2—H2	0.9300	C12—C13	1.482 (4)
C3—C4	1.408 (5)	C13—C14	1.379 (4)
C3—H3	0.9300	C13—C18	1.384 (4)
C4—C5	1.411 (4)	C14—C15	1.377 (5)
C4—H4	0.9300	C14—H14A	0.9300
C5—H5	0.9300	C15—C16	1.368 (5)
C6—C7	1.405 (12)	C15—H15A	0.9300
C6—C10	1.416 (10)	C16—N17	1.323 (4)
C6—H6	0.9300	C16—H16A	0.9300
C7—C8	1.417 (11)	C18—N17	1.334 (4)
C7—H7	0.9300	C18—H18A	0.9300
C8—C9	1.411 (8)	C19—N1	1.134 (4)
C8—H8	0.9300

C8'—Fe1—C9'	37.9 (6)	C4—C5—C1	108.9 (3)
C8'—Fe1—C5	117.0 (7)	C4—C5—Fe1	70.89 (19)
C9'—Fe1—C5	112.2 (5)	C1—C5—Fe1	69.61 (18)
C8'—Fe1—C7	52.6 (7)	C4—C5—H5	125.6
C9'—Fe1—C7	67.9 (6)	C1—C5—H5	125.6
C5—Fe1—C7	164.2 (4)	Fe1—C5—H5	125.5
C8'—Fe1—C10'	65.1 (8)	C7—C6—C10	108.2 (8)
C9'—Fe1—C10'	40.0 (7)	C7—C6—Fe1	69.6 (5)
C5—Fe1—C10'	136.0 (7)	C10—C6—Fe1	70.5 (4)
C7—Fe1—C10'	54.7 (6)	C7—C6—H6	125.9
C8'—Fe1—C6	67.8 (7)	C10—C6—H6	125.9
C9'—Fe1—C6	53.4 (6)	Fe1—C6—H6	125.6
C5—Fe1—C6	152.7 (4)	C6—C7—C8	108.8 (8)
C7—Fe1—C6	40.5 (3)	C6—C7—Fe1	69.8 (5)
C10'—Fe1—C6	18.1 (6)	C8—C7—Fe1	70.1 (5)
C8'—Fe1—C1	146.7 (7)	C6—C7—H7	125.6
C9'—Fe1—C1	116.4 (5)	C8—C7—H7	125.6
C5—Fe1—C1	41.65 (12)	Fe1—C7—H7	126.0
C7—Fe1—C1	153.6 (3)	C9—C8—C7	107.0 (7)
C10'—Fe1—C1	110.3 (6)	C9—C8—Fe1	70.2 (3)
C6—Fe1—C1	118.7 (3)	C7—C8—Fe1	69.1 (5)
C8'—Fe1—C2	171.8 (7)	C9—C8—H8	126.5
C9'—Fe1—C2	146.9 (7)	C7—C8—H8	126.5
C5—Fe1—C2	69.11 (13)	Fe1—C8—H8	125.7
C7—Fe1—C2	120.1 (3)	C8—C9—C10	109.0 (6)
C10'—Fe1—C2	114.8 (7)	C8—C9—Fe1	69.4 (3)
C6—Fe1—C2	109.4 (3)	C10—C9—Fe1	69.7 (3)
C1—Fe1—C2	41.49 (12)	C8—C9—H9	125.5
C8'—Fe1—C8	18.9 (5)	C10—C9—H9	125.5
C9'—Fe1—C8	54.5 (5)	Fe1—C9—H9	126.9
C5—Fe1—C8	125.4 (3)	C6—C10—C9	107.1 (6)
C7—Fe1—C8	40.8 (3)	C6—C10—Fe1	68.9 (4)
C10'—Fe1—C8	72.1 (6)	C9—C10—Fe1	69.8 (3)
C6—Fe1—C8	68.6 (4)	C6—C10—H10	126.5
C1—Fe1—C8	163.7 (3)	C9—C10—H10	126.5
C2—Fe1—C8	153.2 (3)	Fe1—C10—H10	126.5
C8'—Fe1—C3	135.2 (7)	C9'—C10'—C6'	109.4 (18)
C9'—Fe1—C3	172.9 (7)	C9'—C10'—Fe1	69.7 (10)
C5—Fe1—C3	68.07 (14)	C6'—C10'—Fe1	71.3 (13)
C7—Fe1—C3	109.8 (3)	C9'—C10'—H10'	125.3
C10'—Fe1—C3	144.5 (8)	C6'—C10'—H10'	125.3
C6—Fe1—C3	129.4 (3)	Fe1—C10'—H10'	125.3
C1—Fe1—C3	68.78 (13)	C8'—C9'—C10'	107.6 (17)
C2—Fe1—C3	40.17 (13)	C8'—C9'—Fe1	70.7 (10)
C8—Fe1—C3	119.2 (3)	C10'—C9'—Fe1	70.3 (9)
C8'—Fe1—C4	112.4 (6)	C8'—C9'—H9'	126.2
C9'—Fe1—C4	135.5 (7)	C10'—C9'—H9'	126.2
C5—Fe1—C4	40.59 (13)	Fe1—C9'—H9'	124.4
C7—Fe1—C4	127.7 (4)	C9'—C8'—C7'	112.8 (19)
C10'—Fe1—C4	175.1 (8)	C9'—C8'—Fe1	71.4 (10)
C6—Fe1—C4	166.2 (4)	C7'—C8'—Fe1	71.1 (14)
C1—Fe1—C4	69.28 (13)	C9'—C8'—H8'	123.6
C2—Fe1—C4	68.28 (14)	C7'—C8'—H8'	123.6
C8—Fe1—C4	106.9 (2)	Fe1—C8'—H8'	125.5
C3—Fe1—C4	40.22 (13)	C6'—C7'—C8'	102 (2)
C8'—Fe1—C10	54.8 (6)	C6'—C7'—Fe1	69.4 (16)
C9'—Fe1—C10	19.7 (5)	C8'—C7'—Fe1	67.2 (13)
C5—Fe1—C10	117.6 (3)	C6'—C7'—H7'	129.1
C7—Fe1—C10	68.2 (4)	C8'—C7'—H7'	129.1
C10'—Fe1—C10	23.7 (6)	Fe1—C7'—H7'	125.9
C6—Fe1—C10	40.6 (3)	C10'—C6'—C7'	108 (2)
C1—Fe1—C10	106.8 (2)	C10'—C6'—Fe1	68.9 (13)
C2—Fe1—C10	128.4 (3)	C7'—C6'—Fe1	69.7 (17)
C8—Fe1—C10	68.6 (3)	C10'—C6'—H6'	125.9
C3—Fe1—C10	166.7 (3)	C7'—C6'—H6'	125.9
C4—Fe1—C10	151.4 (3)	Fe1—C6'—H6'	127.0
C5—C1—C11	123.4 (3)	C12—C11—C1	129.1 (3)
C5—C1—C2	106.0 (3)	C12—C11—H11A	115.4
C11—C1—C2	130.6 (3)	C1—C11—H11A	115.4
C5—C1—Fe1	68.74 (18)	C11—C12—C19	119.4 (3)
C11—C1—Fe1	124.4 (2)	C11—C12—C13	125.9 (3)
C2—C1—Fe1	69.45 (18)	C19—C12—C13	114.6 (3)
C3—C2—C1	108.2 (3)	C14—C13—C18	116.8 (3)
C3—C2—Fe1	70.3 (2)	C14—C13—C12	121.6 (3)
C1—C2—Fe1	69.06 (17)	C18—C13—C12	121.6 (3)
C3—C2—H2	125.9	C15—C14—C13	119.6 (3)
C1—C2—H2	125.9	C15—C14—H14A	120.2
Fe1—C2—H2	126.3	C13—C14—H14A	120.2
C2—C3—C4	109.4 (3)	C16—C15—C14	118.9 (4)
C2—C3—Fe1	69.54 (19)	C16—C15—H15A	120.5
C4—C3—Fe1	70.06 (19)	C14—C15—H15A	120.5
C2—C3—H3	125.3	N17—C16—C15	123.3 (4)
C4—C3—H3	125.3	N17—C16—H16A	118.3
Fe1—C3—H3	126.7	C15—C16—H16A	118.3
C3—C4—C5	107.6 (3)	N17—C18—C13	124.4 (3)
C3—C4—Fe1	69.7 (2)	N17—C18—H18A	117.8
C5—C4—Fe1	68.52 (19)	C13—C18—H18A	117.8
C3—C4—H4	126.2	N1—C19—C12	177.5 (4)
C5—C4—H4	126.2	C16—N17—C18	117.1 (3)
Fe1—C4—H4	127.1

Experimental details

Crystal data
Chemical formula	[Fe(C₅H₅)(C₁₃H₉N₂)]
M_r	314.16
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	11.552 (3), 9.2557 (15), 14.458 (5)
β (°)	111.679 (15)
V (Å³)	1436.6 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.04
Crystal size (mm)	0.25 × 0.2 × 0.1

Data collection
Diffractometer	Rigaku SCXmini diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.896, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	14447, 3290, 2008
R_int	0.084
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.107, 0.99
No. of reflections	3290
No. of parameters	206
No. of restraints	22
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.27

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

Acknowledgements

This work was supported by a Start-up Grant awarded to H-YY by Southeast University.

References

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