(Z)-3-Ferrocenyl-2-phenyl-acrylonitrile.

In the structure of the title compound, [Fe(C(5)H(5))(C(14)H(10)N)], the unsubstituted cyclo-penta-diene (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 = 313.17

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.126

S = 1.07

3523 reflections

206 parameters

30 restraints

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −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.

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

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

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

[Fe(C5H5)(C14H10N)]	F000 = 648
Mr = 313.17	Dx = 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 = 3.1–27.5º
b = 11.795 (2) Å	µ = 0.97 mm−1
c = 19.939 (4) Å	T = 293 (2) K
β = 106.786 (16)º	Block, red
V = 1536.8 (5) Å3	0.18 × 0.06 × 0.05 mm
Z = 4

Rigaku, SCXmini diffractometer	3523 independent reflections
Radiation source: fine-focus sealed tube	2520 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.050
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5º
T = 293(2) K	θmin = 3.1º
ω scans	h = −8→8
Absorption correction: Multi-scan(CrystalClear; Rigaku, 2005)	k = −15→15
Tmin = 0.892, Tmax = 1.00	l = −25→25
15093 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) = 0.126	w = 1/[σ2(Fo2) + (0.0496P)2 + 0.4337P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
3523 reflections	Δρmax = 0.22 e Å−3
206 parameters	Δρmin = −0.40 e Å−3
30 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 > 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.

	x	y	z	Uiso*/Ueq	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)

	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)

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)