(Z)-3-Ferrocenyl-2-(3-pyrid-yl)-acrylo-nitrile.

The mol-ecular structure of the title compound, [Fe(C(5)H(5))(C(13)H(9)N(2))], (I), is analogous to that of the compound (Z)-3-ferrocenyl-2-phenyl-acrylonitrile [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 cyclo-penta-diene 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 = 314.16

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.107

S = 0.99

3290 reflections

206 parameters

22 restraints

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808025531/ez2133sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808025531/ez2133Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Fe(C5H5)(C13H9N2)]	F000 = 648
Mr = 314.16	Dx = 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 = 2.7–27.5º
b = 9.2557 (15) Å	µ = 1.04 mm−1
c = 14.458 (5) Å	T = 293 (2) K
β = 111.679 (15)º	Block, red
V = 1436.6 (7) Å3	0.25 × 0.2 × 0.1 mm
Z = 4

Rigaku SCXmini diffractometer	3290 independent reflections
Radiation source: fine-focus sealed tube	2008 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.084
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5º
T = 293(2) K	θmin = 2.7º
ω scans	h = −14→14
Absorption correction: Multi-scan(CrystalClear; Rigaku, 2005)	k = −12→12
Tmin = 0.896, Tmax = 1.000	l = −18→18
14447 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.053	H-atom parameters constrained
wR(F2) = 0.107	w = 1/[σ2(Fo2) + (0.0415P)2] where P = (Fo2 + 2Fc2)/3
S = 0.99	(Δ/σ)max = 0.006
3290 reflections	Δρmax = 0.24 e Å−3
206 parameters	Δρmin = −0.27 e Å−3
22 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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.

	x	y	z	Uiso*/Ueq	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)

	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)

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