2-[(Ferrocen-1-yl)(hy-droxy)meth-yl]prop-2-ene-nitrile.

In the title ferrocene derivative, [Fe(C5H5)(C9H8NO)], the dihedral angle between the ene-nitrile group and the substituted cyclo-penta-dienyl ring is 71.2 (1)°. The cyclopentadienyl rings of the ferrocene moiety are arranged in an eclipsed conformation. The hy-droxy group, and the corresponding methine H atom, are disordered over two sets of sites with site-occupancy factors of 0.744 (4) and 0.256 (4). An intra-molecular C-H⋯O close contact is observed. In the crystal, O-H⋯N hydrogen bonds form a C(6) chain along [100].

Related literature

For general background to ferrocene derivatives, see: Li et al. (2013 ▶); Skiba et al. (2012 ▶); Karolyi et al. (2012 ▶). For related structures, see: Leka et al. (2012a ▶,b ▶).

Experimental

Crystal data

[Fe(C5H5)(C9H8NO)]

M = 267.10

Triclinic,

a = 7.4317 (15) Å

b = 8.0137 (16) Å

c = 10.083 (2) Å

α = 92.09 (3)°

β = 93.81 (3)°

γ = 101.09 (3)°

V = 587.3 (2) Å3

Z = 2

Mo Kα radiation

μ = 1.26 mm−1

T = 292 K

0.22 × 0.20 × 0.18 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

6351 measured reflections

2683 independent reflections

2481 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.112

S = 1.06

2683 reflections

160 parameters

3 restraints

H-atom parameters constrained

Δρmax = 0.78 e Å−3

Δρmin = −0.51 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL2013 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813031218/zq2212sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813031218/zq2212Isup2.hkl

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

[Fe(C5H5)(C9H8NO)]	Z = 2
Mr = 267.10	F(000) = 276
Triclinic, P1	Dx = 1.511 Mg m−3
a = 7.4317 (15) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.0137 (16) Å	Cell parameters from 5048 reflections
c = 10.083 (2) Å	θ = 2.6–24.8°
α = 92.09 (3)°	µ = 1.26 mm−1
β = 93.81 (3)°	T = 292 K
γ = 101.09 (3)°	Block, colourless
V = 587.3 (2) Å3	0.22 × 0.20 × 0.18 mm

Bruker SMART APEX CCD area-detector diffractometer	Rint = 0.028
Radiation source: fine-focus sealed tube	θmax = 28.1°, θmin = 2.0°
ω scans	h = −9→9
6351 measured reflections	k = −10→10
2683 independent reflections	l = −13→13
2481 reflections with I > 2σ(I)

Refinement on F2	3 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041	H-atom parameters constrained
wR(F2) = 0.112	w = 1/[σ2(Fo2) + (0.0721P)2 + 0.143P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.001
2683 reflections	Δρmax = 0.78 e Å−3
160 parameters	Δρmin = −0.51 e Å−3

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
Fe1	0.12344 (3)	0.78280 (3)	0.68844 (3)	0.03652 (14)
O1	0.1780 (3)	1.2232 (3)	0.8242 (3)	0.0630 (7)	0.744 (4)
H1	0.0808	1.1576	0.8334	0.094*	0.744 (4)
O1'	0.3410 (9)	1.0729 (9)	0.9630 (6)	0.0630 (7)	0.256 (4)
H1'	0.4204	1.0145	0.9653	0.094*	0.256 (4)
N1	0.7948 (3)	1.1554 (3)	0.8583 (3)	0.0685 (7)
C1	−0.0590 (3)	0.7684 (3)	0.8309 (2)	0.0469 (5)
H1A	−0.0533	0.8494	0.9070	0.056*
C2	−0.1490 (3)	0.7765 (3)	0.7047 (3)	0.0495 (5)
H2	−0.2169	0.8643	0.6770	0.059*
C3	−0.1239 (4)	0.6360 (4)	0.6253 (3)	0.0580 (7)
H3	−0.1711	0.6094	0.5323	0.070*
C4	−0.0192 (4)	0.5410 (3)	0.7013 (3)	0.0592 (7)
H4	0.0191	0.4364	0.6713	0.071*
C5	0.0208 (4)	0.6227 (3)	0.8283 (3)	0.0529 (6)
H5	0.0925	0.5850	0.9025	0.063*
C6	0.3135 (3)	0.9999 (3)	0.7279 (2)	0.0370 (4)
C7	0.2271 (3)	0.9998 (3)	0.5987 (2)	0.0500 (6)
H7	0.1574	1.0840	0.5659	0.060*
C8	0.2586 (4)	0.8557 (4)	0.5254 (3)	0.0637 (8)
H8	0.2132	0.8225	0.4329	0.076*
C9	0.3633 (4)	0.7675 (4)	0.6070 (3)	0.0597 (7)
H9	0.4043	0.6625	0.5817	0.072*
C10	0.3985 (3)	0.8559 (3)	0.7331 (3)	0.0467 (5)
H10	0.4685	0.8232	0.8104	0.056*
C11	0.3231 (3)	1.1352 (3)	0.8366 (2)	0.0400 (4)
H11	0.3218	1.0822	0.9227	0.048*	0.744 (4)
H11'	0.2147	1.1880	0.8276	0.048*	0.256 (4)
C12	0.4964 (3)	1.2685 (3)	0.8351 (2)	0.0438 (5)
C13	0.6643 (3)	1.2065 (3)	0.8478 (2)	0.0464 (5)
C14	0.5015 (4)	1.4309 (4)	0.8248 (4)	0.0779 (10)
H14A	0.6141	1.5058	0.8257	0.093*
H14B	0.3927	1.4719	0.8165	0.093*

	U11	U22	U33	U12	U13	U23
Fe1	0.02602 (18)	0.0411 (2)	0.03825 (19)	−0.00367 (12)	0.00291 (12)	0.00018 (12)
O1	0.0324 (11)	0.0528 (13)	0.103 (2)	0.0050 (9)	0.0150 (11)	−0.0021 (12)
O1'	0.0324 (11)	0.0528 (13)	0.103 (2)	0.0050 (9)	0.0150 (11)	−0.0021 (12)
N1	0.0404 (12)	0.0762 (16)	0.0859 (17)	0.0112 (11)	−0.0096 (11)	−0.0092 (13)
C1	0.0379 (11)	0.0524 (13)	0.0459 (12)	−0.0047 (10)	0.0120 (9)	0.0006 (9)
C2	0.0257 (10)	0.0587 (14)	0.0610 (14)	−0.0013 (9)	0.0059 (9)	0.0095 (11)
C3	0.0390 (12)	0.0699 (17)	0.0520 (13)	−0.0194 (11)	0.0021 (10)	−0.0081 (12)
C4	0.0482 (14)	0.0414 (12)	0.0826 (18)	−0.0087 (10)	0.0201 (13)	−0.0034 (12)
C5	0.0424 (12)	0.0532 (14)	0.0602 (14)	−0.0018 (10)	0.0081 (10)	0.0183 (11)
C6	0.0262 (9)	0.0397 (10)	0.0420 (10)	−0.0015 (7)	0.0018 (7)	0.0044 (8)
C7	0.0408 (12)	0.0600 (14)	0.0424 (11)	−0.0091 (10)	0.0014 (9)	0.0140 (10)
C8	0.0546 (16)	0.0820 (19)	0.0410 (12)	−0.0224 (14)	0.0153 (11)	−0.0083 (12)
C9	0.0375 (12)	0.0615 (16)	0.0745 (18)	−0.0049 (11)	0.0198 (12)	−0.0197 (13)
C10	0.0261 (9)	0.0467 (12)	0.0640 (14)	0.0007 (8)	0.0004 (9)	−0.0024 (10)
C11	0.0301 (10)	0.0391 (10)	0.0482 (11)	−0.0006 (8)	0.0059 (8)	0.0035 (8)
C12	0.0311 (10)	0.0427 (11)	0.0547 (12)	0.0002 (8)	0.0035 (9)	−0.0022 (9)
C13	0.0321 (11)	0.0499 (12)	0.0521 (12)	−0.0022 (9)	−0.0008 (9)	−0.0052 (9)
C14	0.0422 (14)	0.0460 (15)	0.143 (3)	−0.0022 (12)	0.0181 (17)	0.0090 (17)

Fe1—C6	2.027 (2)	C3—H3	0.9800
Fe1—C5	2.029 (2)	C4—C5	1.404 (4)
Fe1—C8	2.029 (3)	C4—H4	0.9800
Fe1—C10	2.030 (2)	C5—H5	0.9800
Fe1—C1	2.031 (2)	C6—C7	1.414 (3)
Fe1—C3	2.032 (2)	C6—C10	1.419 (3)
Fe1—C7	2.032 (2)	C6—C11	1.501 (3)
Fe1—C2	2.033 (2)	C7—C8	1.413 (4)
Fe1—C9	2.034 (3)	C7—H7	0.9800
Fe1—C4	2.035 (3)	C8—C9	1.397 (5)
O1—C11	1.399 (3)	C8—H8	0.9800
O1—H1	0.8200	C9—C10	1.416 (4)
O1'—C11	1.394 (6)	C9—H9	0.9800
O1'—H1'	0.8200	C10—H10	0.9800
N1—C13	1.124 (3)	C11—C12	1.508 (3)
C1—C2	1.408 (4)	C11—H11	0.9800
C1—C5	1.408 (4)	C11—H11'	0.9800
C1—H1A	0.9800	C12—C14	1.303 (4)
C2—C3	1.406 (4)	C12—C13	1.429 (3)
C2—H2	0.9800	C14—H14A	0.9300
C3—C4	1.402 (4)	C14—H14B	0.9300
C6—Fe1—C5	124.47 (10)	C2—C3—H3	125.8
C6—Fe1—C8	68.46 (10)	Fe1—C3—H3	125.8
C5—Fe1—C8	156.88 (14)	C3—C4—C5	107.7 (2)
C6—Fe1—C10	40.94 (9)	C3—C4—Fe1	69.70 (15)
C5—Fe1—C10	107.84 (11)	C5—C4—Fe1	69.54 (15)
C8—Fe1—C10	68.20 (12)	C3—C4—H4	126.2
C6—Fe1—C1	107.63 (10)	C5—C4—H4	126.2
C5—Fe1—C1	40.59 (11)	Fe1—C4—H4	126.2
C8—Fe1—C1	161.02 (14)	C4—C5—C1	108.4 (2)
C10—Fe1—C1	121.84 (11)	C4—C5—Fe1	70.04 (15)
C6—Fe1—C3	157.18 (12)	C1—C5—Fe1	69.80 (14)
C5—Fe1—C3	67.81 (12)	C4—C5—H5	125.8
C8—Fe1—C3	107.91 (11)	C1—C5—H5	125.8
C10—Fe1—C3	160.59 (12)	Fe1—C5—H5	125.8
C1—Fe1—C3	68.06 (11)	C7—C6—C10	107.8 (2)
C6—Fe1—C7	40.76 (9)	C7—C6—C11	125.7 (2)
C5—Fe1—C7	161.10 (12)	C10—C6—C11	126.4 (2)
C8—Fe1—C7	40.73 (12)	C7—C6—Fe1	69.79 (13)
C10—Fe1—C7	68.59 (11)	C10—C6—Fe1	69.64 (12)
C1—Fe1—C7	124.28 (11)	C11—C6—Fe1	128.96 (15)
C3—Fe1—C7	121.75 (11)	C8—C7—C6	107.6 (2)
C6—Fe1—C2	121.64 (10)	C8—C7—Fe1	69.52 (15)
C5—Fe1—C2	68.07 (11)	C6—C7—Fe1	69.45 (13)
C8—Fe1—C2	124.44 (13)	C8—C7—H7	126.2
C10—Fe1—C2	157.38 (11)	C6—C7—H7	126.2
C1—Fe1—C2	40.53 (10)	Fe1—C7—H7	126.2
C3—Fe1—C2	40.49 (11)	C9—C8—C7	108.8 (2)
C7—Fe1—C2	107.66 (11)	C9—C8—Fe1	70.09 (15)
C6—Fe1—C9	68.68 (10)	C7—C8—Fe1	69.75 (14)
C5—Fe1—C9	121.88 (13)	C9—C8—H8	125.6
C8—Fe1—C9	40.22 (13)	C7—C8—H8	125.6
C10—Fe1—C9	40.79 (10)	Fe1—C8—H8	125.6
C1—Fe1—C9	157.44 (13)	C8—C9—C10	108.0 (2)
C3—Fe1—C9	124.04 (11)	C8—C9—Fe1	69.69 (16)
C7—Fe1—C9	68.38 (12)	C10—C9—Fe1	69.46 (14)
C2—Fe1—C9	160.49 (12)	C8—C9—H9	126.0
C6—Fe1—C4	160.96 (12)	C10—C9—H9	126.0
C5—Fe1—C4	40.42 (12)	Fe1—C9—H9	126.0
C8—Fe1—C4	121.56 (13)	C9—C10—C6	107.8 (2)
C10—Fe1—C4	124.15 (12)	C9—C10—Fe1	69.75 (14)
C1—Fe1—C4	68.23 (11)	C6—C10—Fe1	69.42 (12)
C3—Fe1—C4	40.33 (12)	C9—C10—H10	126.1
C7—Fe1—C4	156.93 (13)	C6—C10—H10	126.1
C2—Fe1—C4	68.13 (12)	Fe1—C10—H10	126.1
C9—Fe1—C4	107.59 (12)	O1'—C11—C6	112.5 (4)
C11—O1—H1	109.5	O1—C11—C6	113.0 (2)
C11—O1'—H1'	109.5	O1'—C11—C12	102.2 (3)
C2—C1—C5	107.7 (2)	O1—C11—C12	105.74 (19)
C2—C1—Fe1	69.80 (13)	C6—C11—C12	111.08 (18)
C5—C1—Fe1	69.61 (14)	O1—C11—H11	109.0
C2—C1—H1A	126.2	C6—C11—H11	109.0
C5—C1—H1A	126.2	C12—C11—H11	109.0
Fe1—C1—H1A	126.2	O1'—C11—H11'	110.3
C3—C2—C1	107.8 (2)	C6—C11—H11'	110.3
C3—C2—Fe1	69.71 (15)	C12—C11—H11'	110.3
C1—C2—Fe1	69.67 (14)	C14—C12—C13	119.6 (2)
C3—C2—H2	126.1	C14—C12—C11	124.9 (2)
C1—C2—H2	126.1	C13—C12—C11	115.5 (2)
Fe1—C2—H2	126.1	N1—C13—C12	178.9 (3)
C4—C3—C2	108.5 (2)	C12—C14—H14A	120.0
C4—C3—Fe1	69.98 (15)	C12—C14—H14B	120.0
C2—C3—Fe1	69.81 (14)	H14A—C14—H14B	120.0
C4—C3—H3	125.8
C5—C1—C2—C3	0.0 (3)	C7—C8—C9—Fe1	59.20 (18)
Fe1—C1—C2—C3	59.52 (17)	C8—C9—C10—C6	0.1 (3)
C5—C1—C2—Fe1	−59.55 (17)	Fe1—C9—C10—C6	−59.20 (16)
C1—C2—C3—C4	0.0 (3)	C8—C9—C10—Fe1	59.25 (18)
Fe1—C2—C3—C4	59.50 (18)	C7—C6—C10—C9	−0.2 (3)
C1—C2—C3—Fe1	−59.49 (16)	C11—C6—C10—C9	−176.6 (2)
C2—C3—C4—C5	0.0 (3)	Fe1—C6—C10—C9	59.40 (17)
Fe1—C3—C4—C5	59.42 (18)	C7—C6—C10—Fe1	−59.58 (16)
C2—C3—C4—Fe1	−59.39 (17)	C11—C6—C10—Fe1	124.0 (2)
C3—C4—C5—C1	0.0 (3)	C7—C6—C11—O1'	153.7 (4)
Fe1—C4—C5—C1	59.47 (17)	C10—C6—C11—O1'	−30.5 (4)
C3—C4—C5—Fe1	−59.51 (18)	Fe1—C6—C11—O1'	61.8 (4)
C2—C1—C5—C4	0.0 (3)	C7—C6—C11—O1	26.2 (3)
Fe1—C1—C5—C4	−59.62 (18)	C10—C6—C11—O1	−158.0 (2)
C2—C1—C5—Fe1	59.66 (16)	Fe1—C6—C11—O1	−65.7 (3)
C10—C6—C7—C8	0.2 (3)	C7—C6—C11—C12	−92.4 (2)
C11—C6—C7—C8	176.7 (2)	C10—C6—C11—C12	83.3 (3)
Fe1—C6—C7—C8	−59.26 (17)	Fe1—C6—C11—C12	175.68 (15)
C10—C6—C7—Fe1	59.49 (15)	O1'—C11—C12—C14	−116.6 (4)
C11—C6—C7—Fe1	−124.1 (2)	O1—C11—C12—C14	0.3 (4)
C6—C7—C8—C9	−0.2 (3)	C6—C11—C12—C14	123.2 (3)
Fe1—C7—C8—C9	−59.41 (19)	O1'—C11—C12—C13	62.6 (4)
C6—C7—C8—Fe1	59.21 (16)	O1—C11—C12—C13	179.5 (2)
C7—C8—C9—C10	0.1 (3)	C6—C11—C12—C13	−57.5 (3)
Fe1—C8—C9—C10	−59.11 (18)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1i	0.82	2.15	2.841 (3)	141
C14—H14B···O1	0.93	2.31	2.648 (4)	101

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1i	0.82	2.15	2.841 (3)	141
C14—H14B⋯O1	0.93	2.31	2.648 (4)	101

Symmetry code: (i) .