Ferrocenylbutadiyne.

The title compound, [Fe(C(5)H(5))(C(9)H(5))], crystallizes in a form of a π-π-stacked assembly formed as a result of strong inter-molecular π-π inter-actions between (a) the triple bonds of two neighboring butadiyne substituents overlapping in a 'head-to-tail' fashion [characterized by C⋯C short contacts of 3.622 (5), 3.567 (6) and 3.556 (6) Å] and (b) the triple bonds of the butadiyne substituent and substituted cyclo-pendadiene ring of neighboring mol-ecules [C⋯C = 3.474 (5) and 3.492 (6) Å]. The linear butadiyne substituent has alternating C-C triple and single bonds, while the unsubstituted cyclo-penta-diene ring is slightly positionally disordered (although the structure reported here was solved as non-disordered) and retains a close to eclipsed conformation.

Related literature

For the general synthesis and applications of substituted ferrocenes and related macrocycles, see: Fouda et al. (2007 ▶); Nemykin et al. (2001 ▶, 2007a ▶,b ▶, 2008 ▶); Stepnika (2008 ▶); Osakada et al. (2006 ▶). For the synthesis of the title compound, see: Yuan et al. (1993 ▶); Nemykin et al. (2007c ▶). For examples of the use of the title compound, see Bruce et al. (2004 ▶).

Experimental

Crystal data

[Fe(C5H5)(C9H5)]

M = 234.08

Monoclinic,

a = 7.9438 (16) Å

b = 10.332 (2) Å

c = 12.835 (3) Å

β = 97.01 (3)°

V = 1045.5 (4) Å3

Z = 4

Mo Kα radiation

μ = 1.40 mm−1

T = 298 K

0.45 × 0.30 × 0.25 mm

Data collection

Rigaku AFC-7R diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.58, T max = 0.70

2549 measured reflections

2411 independent reflections

2248 reflections with I > 2σ(I)

R int = 0.052

3 standard reflections every 150 reflections intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.136

S = 1.08

2402 reflections

136 parameters

H-atom parameters constrained

Δρmax = 0.52 e Å−3

Δρmin = −0.47 e Å−3

Data collection: AFC-7R Diffractometer Control Software (Rigaku/MSC, 1997 ▶); cell refinement: WinAFC (Rigaku/MSC, 2000 ▶); data reduction: TEXSAN (Rigaku/MSC, 2004 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003 ▶); molecular graphics: CAMERON (Watkin et al., 1996 ▶); software used to prepare material for publication: CRYSTALS.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809005522/hg2474sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809005522/hg2474Isup2.hkl

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

[Fe(C5H5)(C9H5)]	F(000) = 480
Mr = 234.08	Dx = 1.487 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 7.9438 (16) Å	θ = 15–18°
b = 10.332 (2) Å	µ = 1.40 mm−1
c = 12.835 (3) Å	T = 298 K
β = 97.01 (3)°	Block, brown
V = 1045.5 (4) Å3	0.45 × 0.30 × 0.25 mm
Z = 4

Rigaku AFC-7R diffractometer	Rint = 0.052
graphite	θmax = 27.5°, θmin = 2.5°
ω/2θ scans	h = −10→10
Absorption correction: ψ scan (North et al., 1968)	k = −13→0
Tmin = 0.58, Tmax = 0.70	l = 0→16
2549 measured reflections	3 standard reflections every 150 reflections
2411 independent reflections	intensity decay: 0.00%
2248 reflections with I > 2σ(I)

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.048	H-atom parameters constrained
wR(F2) = 0.136	Method = Modified Sheldrick w = 1/[σ2(F2) + (0.07P)2 + 0.99P], where P = [max(Fo2,0) + 2Fc2]/3
S = 1.08	(Δ/σ)max = 0.0003
2402 reflections	Δρmax = 0.52 e Å−3
136 parameters	Δρmin = −0.47 e Å−3
0 restraints

	x	y	z	Uiso*/Ueq
Fe1	0.29866 (5)	0.10003 (4)	0.31022 (3)	0.0488
C1	0.1074 (4)	0.0794 (3)	0.4007 (3)	0.0518
C2	0.2591 (4)	0.0175 (3)	0.4488 (3)	0.0575
C3	0.3047 (5)	−0.0793 (3)	0.3799 (3)	0.0668
C4	0.1850 (6)	−0.0782 (3)	0.2897 (3)	0.0710
C5	0.0628 (4)	0.0191 (4)	0.3004 (3)	0.0622
C6	0.3496 (7)	0.2904 (4)	0.2979 (5)	0.0866
C7	0.4938 (7)	0.2257 (5)	0.3366 (4)	0.0928
C8	0.5285 (7)	0.1368 (5)	0.2642 (8)	0.1210
C9	0.4034 (14)	0.1459 (8)	0.1794 (5)	0.1336
C10	0.2955 (7)	0.2426 (7)	0.2031 (5)	0.1036
C11	0.0220 (4)	0.1842 (3)	0.4417 (3)	0.0543
C12	−0.0531 (4)	0.2707 (4)	0.4767 (3)	0.0594
C13	−0.1411 (5)	0.3705 (4)	0.5177 (3)	0.0665
C14	−0.2128 (5)	0.4495 (4)	0.5504 (4)	0.0755
H2	0.3169	0.0377	0.5142	0.0693*
H3	0.3970	−0.1349	0.3926	0.0865*
H4	0.1871	−0.1323	0.2320	0.0850*
H5	−0.0298	0.0394	0.2515	0.0744*
H6	0.2992	0.3561	0.3327	0.1061*
H7	0.5582	0.2387	0.4013	0.1128*
H8	0.6195	0.0796	0.2682	0.1788*
H9	0.3901	0.0972	0.1180	0.1600*
H10	0.2000	0.2722	0.1607	0.1248*
H15	−0.2661	0.5084	0.5739	0.0916*

	U11	U22	U33	U12	U13	U23
Fe1	0.0479 (3)	0.0438 (3)	0.0572 (3)	−0.00690 (17)	0.01690 (19)	−0.00211 (17)
C1	0.0481 (15)	0.0538 (16)	0.0560 (16)	−0.0080 (13)	0.0158 (13)	−0.0011 (13)
C2	0.0606 (18)	0.0546 (17)	0.0591 (17)	−0.0015 (15)	0.0146 (14)	0.0087 (14)
C3	0.070 (2)	0.0454 (17)	0.090 (3)	0.0012 (15)	0.029 (2)	0.0067 (17)
C4	0.084 (3)	0.0535 (18)	0.083 (3)	−0.0227 (18)	0.038 (2)	−0.0177 (17)
C5	0.0541 (17)	0.069 (2)	0.0638 (18)	−0.0216 (16)	0.0107 (14)	−0.0091 (16)
C6	0.099 (3)	0.0441 (18)	0.128 (4)	−0.008 (2)	0.060 (3)	0.005 (2)
C7	0.082 (3)	0.099 (4)	0.093 (3)	−0.051 (3)	−0.003 (2)	0.017 (3)
C8	0.085 (4)	0.068 (3)	0.229 (8)	0.006 (3)	0.096 (5)	0.031 (4)
C9	0.206 (8)	0.120 (5)	0.093 (4)	−0.098 (5)	0.095 (5)	−0.043 (4)
C10	0.079 (3)	0.125 (4)	0.103 (4)	−0.035 (3)	−0.005 (3)	0.061 (4)
C11	0.0476 (16)	0.0597 (18)	0.0577 (17)	−0.0082 (14)	0.0149 (13)	0.0007 (14)
C12	0.0527 (17)	0.064 (2)	0.0631 (19)	−0.0020 (15)	0.0138 (14)	−0.0029 (15)
C13	0.058 (2)	0.073 (2)	0.070 (2)	−0.0079 (18)	0.0147 (17)	−0.0011 (18)
C14	0.073 (2)	0.066 (2)	0.091 (3)	0.0128 (19)	0.028 (2)	−0.018 (2)

Fe1—C1	2.032 (3)	C4—C5	1.416 (6)
Fe1—C2	2.031 (3)	C4—H4	0.930
Fe1—C3	2.056 (3)	C5—H5	0.930
Fe1—C4	2.054 (3)	C6—C7	1.366 (7)
Fe1—C5	2.042 (3)	C6—C10	1.335 (8)
Fe1—C6	2.018 (4)	C6—H6	0.930
Fe1—C7	2.019 (4)	C7—C8	1.359 (8)
Fe1—C8	2.023 (4)	C7—H7	0.930
Fe1—C9	2.019 (4)	C8—C9	1.384 (10)
Fe1—C10	2.013 (4)	C8—H8	0.930
C1—C2	1.436 (5)	C9—C10	1.375 (10)
C1—C5	1.435 (5)	C9—H9	0.930
C1—C11	1.413 (5)	C10—H10	0.930
C2—C3	1.412 (5)	C11—C12	1.192 (5)
C2—H2	0.930	C12—C13	1.385 (5)
C3—C4	1.406 (6)	C13—C14	1.107 (5)
C3—H3	0.930	C14—H15	0.820
C1—Fe1—C2	41.37 (14)	Fe1—C2—H2	125.7
C1—Fe1—C3	68.68 (14)	C3—C2—H2	126.0
C2—Fe1—C3	40.40 (15)	C2—C3—Fe1	68.87 (19)
C1—Fe1—C4	68.39 (14)	C2—C3—C4	108.1 (3)
C2—Fe1—C4	67.87 (16)	Fe1—C3—C4	69.9 (2)
C3—Fe1—C4	40.00 (18)	C2—C3—H3	125.8
C1—Fe1—C5	41.25 (13)	Fe1—C3—H3	127.5
C2—Fe1—C5	69.11 (15)	C4—C3—H3	126.1
C3—Fe1—C5	68.30 (16)	C3—C4—Fe1	70.1 (2)
C4—Fe1—C5	40.45 (16)	C3—C4—C5	109.2 (3)
C1—Fe1—C6	108.53 (16)	Fe1—C4—C5	69.31 (19)
C2—Fe1—C6	122.10 (19)	C3—C4—H4	125.2
C3—Fe1—C6	156.7 (2)	Fe1—C4—H4	126.1
C4—Fe1—C6	162.4 (2)	C5—C4—H4	125.6
C5—Fe1—C6	125.9 (2)	C1—C5—C4	107.3 (3)
C1—Fe1—C7	125.7 (2)	C1—C5—Fe1	69.02 (17)
C2—Fe1—C7	108.70 (18)	C4—C5—Fe1	70.2 (2)
C3—Fe1—C7	122.0 (2)	C1—C5—H5	126.5
C4—Fe1—C7	156.2 (2)	C4—C5—H5	126.1
C5—Fe1—C7	162.5 (2)	Fe1—C5—H5	126.4
C1—Fe1—C8	162.0 (3)	Fe1—C6—C7	70.2 (2)
C2—Fe1—C8	125.2 (3)	Fe1—C6—C10	70.4 (3)
C3—Fe1—C8	108.8 (2)	C7—C6—C10	108.2 (5)
C4—Fe1—C8	122.0 (2)	Fe1—C6—H6	124.8
C5—Fe1—C8	156.0 (3)	C7—C6—H6	125.0
C1—Fe1—C9	155.8 (4)	C10—C6—H6	126.7
C2—Fe1—C9	161.8 (4)	C6—C7—Fe1	70.2 (2)
C3—Fe1—C9	125.7 (3)	C6—C7—C8	108.3 (5)
C4—Fe1—C9	108.88 (19)	Fe1—C7—C8	70.5 (3)
C5—Fe1—C9	120.9 (3)	C6—C7—H7	126.8
C1—Fe1—C10	121.2 (2)	Fe1—C7—H7	124.8
C2—Fe1—C10	156.2 (3)	C8—C7—H7	124.9
C3—Fe1—C10	162.7 (3)	Fe1—C8—C7	70.2 (3)
C4—Fe1—C10	126.9 (2)	Fe1—C8—C9	69.8 (3)
C5—Fe1—C10	108.81 (18)	C7—C8—C9	107.8 (5)
C6—Fe1—C7	39.6 (2)	Fe1—C8—H8	126.0
C6—Fe1—C8	66.3 (2)	C7—C8—H8	127.8
C7—Fe1—C8	39.3 (3)	C9—C8—H8	124.4
C6—Fe1—C9	66.4 (2)	C8—C9—Fe1	70.1 (3)
C7—Fe1—C9	66.6 (2)	C8—C9—C10	106.5 (5)
C8—Fe1—C9	40.0 (3)	Fe1—C9—C10	69.8 (3)
C6—Fe1—C10	38.7 (2)	C8—C9—H9	128.7
C7—Fe1—C10	65.8 (2)	Fe1—C9—H9	124.2
C8—Fe1—C10	66.4 (2)	C10—C9—H9	124.8
C9—Fe1—C10	39.9 (3)	C9—C10—Fe1	70.3 (3)
Fe1—C1—C2	69.28 (18)	C9—C10—C6	109.3 (5)
Fe1—C1—C5	69.73 (18)	Fe1—C10—C6	70.9 (3)
C2—C1—C5	107.2 (3)	C9—C10—H10	126.6
Fe1—C1—C11	124.0 (2)	Fe1—C10—H10	125.6
C2—C1—C11	126.6 (3)	C6—C10—H10	124.1
C5—C1—C11	126.1 (3)	C1—C11—C12	178.5 (3)
C1—C2—Fe1	69.34 (18)	C11—C12—C13	179.5 (4)
C1—C2—C3	108.2 (3)	C12—C13—C14	179.3 (5)
Fe1—C2—C3	70.7 (2)	C13—C14—H15	179.3
C1—C2—H2	125.8