3-Ferrocenyl-2-(4-nitro­phen­yl)acrylonitrile

Nyamori, V.O.; Moodley, N.N.

doi:10.1107/S160053681103306X

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page m1293

doi:10.1107/S160053681103306X

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3-Ferrocenyl-2-(4-nitrophenyl)acrylonitrile

Vincent O. Nyamori ^a ^* and Narainamah N. Moodley ^a

^aSchool of Chemistry, University of KwaZulu-Natal, Westville Campus, Private Bag X54001, Durban, 4000, South Africa
^*Correspondence e-mail: nyamori@ukzn.ac.za

(Received 5 July 2011; accepted 15 August 2011; online 27 August 2011)

In the title compound, [Fe(C₅H₅)(C₁₄H₉N₂O₂)], the ferrocenyl rings exhibit an eclipsed conformation with a staggering angle of 15.9°, which is quite large compared to similar compounds.

Related literature

For background to ferrocene chemistry, see: Štěpnička (2008 ); Gooding et al. (1983 ); Togni & Hayashi (1995 ). For related ferrocenylacrylonitrile structures, see: Cao & Ye (2008 ); Imrie et al. (2007 ). For the synthesis of acrylonitriles, see: Liu et al. (2001 ); Jeffery (1999 ); El-Tammany et al. (1983 ); Imrie et al. (2007).

Experimental

Crystal data

[Fe(C₅H₅)(C₁₄H₉N₂O₂)]
M_r = 358.17
Monoclinic, P 2₁ /n
a = 6.7186 (14) Å
b = 28.036 (6) Å
c = 8.4165 (18) Å
β = 90.108 (6)°
V = 1585.3 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.96 mm⁻¹
T = 173 K
0.53 × 0.05 × 0.02 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.629, T_max = 0.981
9108 measured reflections
2672 independent reflections
1437 reflections with I > 2σ(I)
R_int = 0.112

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.114
S = 0.90
2672 reflections
218 parameters
H-atom parameters constrained
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.65 e Å⁻³

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT-Plus (Bruker, 2005); data reduction: SAINT-Plus; 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: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681103306X/gw2107sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681103306X/gw2107Isup2.hkl

checkCIF report

Comment top

The synthesis of acrylonitrile compounds has previously been achieved by the use of Wittig reactions (Liu et al., 2001), Heck reactions (Jeffery et al., 1999) and McMurry coupling reactions (El-Tammany et al., 1983). The growing interest in their synthesis and of their related derivatives, especially those with ferrocenyl moiety incorporated, is due to the fact that they are known to be important substrates for applications in material science (Štěpnička, 2008 and Togni & Hayashi, 1995). One of the major driving forces into their research is due to their ability to generate new materials with large second-order non-linear optical (NLO) features which in turn makes them useful in the field such application as photoactive semiconductors (Gooding, et al. 1983). The solvent-free reaction involved adding equimolar quantities of ferrocenecarboxaldehyde and 4-nitrophenylacetonitrile into a Pyrex tube. A catalytic amount of piperidine was added to act as a base. The reagents were thoroughly mixed, ground and then allowed to dry in the open air before being analysed by use of IR spectroscopy, 1H- and 13 C-NMR spectroscopy to determine the reaction progress. This reaction occurred readily and was characterized by the formation of a dark purple melt. The favourable reaction is due to the strong inductive effect of the nitro group which contributes to the activation of the methylene group taking part in the reaction. This could be explained by the kind of mechanism that operates in the Knoevenagel reaction where the strong electron withdrawing group (NO2 and CN) is expected to stabilize the intermediate. The molecule is characterized by two planes i.e. nitrile-ethylene and nitro-phenyl moieties which are almost coplanar with the torsion angles of C19–C12–C13–C14 being -8.8 (7) while C19–C12–C13–C18 is 6.0 (7)°. The nitro group of the nitrophenyl moiety is slightly twisted from the plane of the phenyl ring, with the torsion angles of C17–C16–N2–O1 and C15–C16–N2–O2 being 6.9 (7) and 6.5 (7) respectively. The ferrocenyl rings have an eclipsed conformation with a staggering angle of 15.9° which is quite large compared to a similar compound such as 3-ferrocenyl-2-(4-cyanophenyl)acrylonitrile (Imrie et al., 2007) with an angle of 1.9°. The single C–C bonds around the ethylene group have a bond distance of 1.427 (7) Å for the C10–C11, which is shorter than C12–C14, 1.475 (7) Å. This difference in bond lengths has also been observed by Cao et al. (2008) and Imrie et al. (2007).

Related literature top

For background to ferrocene chemistry, see: Štěpnička (2008); Gooding et al. (1983); Togni & Hayashi (1995). For related ferrocenylacrylonitrile structures, see: Cao & Ye (2008); Imrie et al. (2007). For the synthesis of acrylonitriles, see: Liu et al. (2001); Jeffery (1999); El-Tammany et al. (1983); Imrie et al. (2007).

Experimental top

Into a Pyrex tube fitted with a ground glass joint, was added an equimolar quantity of ferrocenecarboxaldehyde (200.2 mg, 0.9353 mmol) and 4-nitrophenylacetonitrile (150.7 mg, 0.9294 mmol). The compounds were thoroughly mixed and ground. Thereafter, two drops of piperidine was added to the solid mixture. The reaction mixture rapidly changed into a purple melt which was allowed to dry into a dark purple solid as a crude product. The product was further subjected to column chromatography using hexane/diethyl ether (4:1) as the eluting solvent to achieve purple crystals (330 mg, 99%) m.p. 195°C; IR (KBr cm-1) 3096, 3056, 2218, 1602, 1579, 1511, 1456, 1371, 1253, 1199, 1199, 1049, 1032, 1001, 847, 823, 752, 689; 1H-NMR (CDCl3) 8.29 (2H, d, J 8.9, ArH), 7.77 (2H, d, J 8.9, ArH), 7.61 (1H, s, CH), 5.05 (2H, t, J 1.8, C5H4), 4.68 (2H, t, J 1.8, C5H4), 4.29 (5H, s, C5H5); 13 C-NMR (CDCl3) 147.87, 147.31, 141.35, 125.89, 124.87, 118.77, 104.41, 76.90, 73.21, 71.21, 70.59; m/z (EI) 359 (M+ +1, 12%), 358 (M+, 55%), 312 (7), 191 (6), 190 (12), 165 (6), 121 (25), 56 (6), 32 (19), 28 (100); Anal. Calc for C19H14N2O2Fe: C, 63.7; H, 3.9; N, 7.8; [M+], 358.040467; Found: C, 64.2; H, 4.3; N, 7.5; [M+], 358.040422.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT-Plus (Bruker, 2005); data reduction: SAINT-Plus (Bruker, 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: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. View of (I) (50% probability displacement ellipsoids).

3-Ferrocenyl-2-(4-nitrophenyl)acrylonitrile top

Crystal data top

[Fe(C₅H₅)(C₁₄H₉N₂O₂)]	F(000) = 736
M_r = 358.17	D_x = 1.501 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1007 reflections
a = 6.7186 (14) Å	θ = 2.5–22.0°
b = 28.036 (6) Å	µ = 0.96 mm⁻¹
c = 8.4165 (18) Å	T = 173 K
β = 90.108 (6)°	Needle, brown
V = 1585.3 (6) Å³	0.53 × 0.05 × 0.02 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	1437 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.112
ϕ and ω scans	θ_max = 25°, θ_min = 0.7°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −7→7
T_min = 0.629, T_max = 0.981	k = −24→33
9108 measured reflections	l = −10→9
2672 independent 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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.114	H-atom parameters constrained
S = 0.90	w = 1/[σ²(F_o²) + (0.041P)²] where P = (F_o² + 2F_c²)/3
2672 reflections	(Δ/σ)_max = 0.001
218 parameters	Δρ_max = 0.36 e Å⁻³
0 restraints	Δρ_min = −0.65 e Å⁻³

Crystal data top

[Fe(C₅H₅)(C₁₄H₉N₂O₂)]	V = 1585.3 (6) Å³
M_r = 358.17	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 6.7186 (14) Å	µ = 0.96 mm⁻¹
b = 28.036 (6) Å	T = 173 K
c = 8.4165 (18) Å	0.53 × 0.05 × 0.02 mm
β = 90.108 (6)°

Data collection top

Bruker APEXII CCD diffractometer	2672 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1437 reflections with I > 2σ(I)
T_min = 0.629, T_max = 0.981	R_int = 0.112
9108 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.114	H-atom parameters constrained
S = 0.90	Δρ_max = 0.36 e Å⁻³
2672 reflections	Δρ_min = −0.65 e Å⁻³
218 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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.

The following ALERTS were generated. Each ALERT has the format test-name_ALERT_alert-type_alert-level.

PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ······. 0.962

Noted PLAT220_ALERT_2_C Large Non-Solvent C U_eq(max)/U_eq(min) ··· 3.1 Ratio

No atoms missing from model. Structure complete. R factor = 5%. PLAT241_ALERT_2_C Check High U_eq as Compared to Neighbors for C3 PLAT242_ALERT_2_C Check Low U_eq as Compared to Neighbors for Fe1

Noted. PLAT341_ALERT_3_C Low Bond Precision on C—C Bonds ··············· 0.0081 A ng PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.595 105

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.7532 (9)	0.1921 (2)	0.2707 (7)	0.0432 (16)
H1	0.7278	0.1702	0.1871	0.052*
C2	0.6179 (11)	0.2232 (3)	0.3360 (8)	0.063 (2)
H2	0.4823	0.226	0.3052	0.075*
C3	0.7118 (13)	0.2501 (2)	0.4554 (8)	0.071 (2)
H3	0.6523	0.274	0.5199	0.086*
C4	0.9119 (12)	0.2348 (3)	0.4607 (7)	0.062 (2)
H4	1.0128	0.2471	0.5285	0.074*
C5	0.9355 (9)	0.1985 (2)	0.3497 (7)	0.0461 (17)
H5	1.0544	0.1811	0.3306	0.055*
C6	0.4953 (8)	0.13772 (19)	0.5817 (7)	0.0342 (15)
H6	0.3697	0.135	0.5304	0.041*
C7	0.5441 (9)	0.1706 (2)	0.7033 (7)	0.0426 (16)
H7	0.4561	0.1933	0.7487	0.051*
C8	0.7447 (10)	0.16392 (19)	0.7455 (7)	0.0430 (16)
H8	0.8162	0.1815	0.8234	0.052*
C9	0.8213 (8)	0.1265 (2)	0.6515 (7)	0.0355 (15)
H9	0.9537	0.1147	0.6556	0.043*
C10	0.6672 (7)	0.10918 (18)	0.5490 (6)	0.0276 (14)
C11	0.6982 (7)	0.07124 (18)	0.4387 (6)	0.0244 (13)
H11	0.8338	0.0636	0.4199	0.029*
C12	0.5657 (7)	0.04438 (18)	0.3566 (6)	0.0235 (13)
C13	0.6178 (7)	0.00500 (18)	0.2482 (6)	0.0233 (13)
C14	0.4696 (8)	−0.02564 (19)	0.1894 (6)	0.0285 (14)
H14	0.3345	−0.0199	0.2162	0.034*
C15	0.5161 (8)	−0.0640 (2)	0.0932 (6)	0.0322 (15)
H15	0.4146	−0.0841	0.0519	0.039*
C16	0.7119 (8)	−0.07241 (18)	0.0592 (6)	0.0292 (13)
C17	0.8631 (8)	−0.0431 (2)	0.1144 (7)	0.0391 (16)
H17	0.9981	−0.0497	0.0889	0.047*
C18	0.8141 (7)	−0.0042 (2)	0.2070 (6)	0.0312 (14)
H18	0.9162	0.0166	0.2432	0.037*
C19	0.3559 (8)	0.05321 (19)	0.3775 (7)	0.0304 (14)
N1	0.1881 (7)	0.05873 (18)	0.3927 (6)	0.0506 (15)
N2	0.7683 (9)	−0.11443 (17)	−0.0399 (6)	0.0459 (14)
O1	0.9458 (7)	−0.12327 (16)	−0.0540 (6)	0.0688 (15)
O2	0.6336 (7)	−0.13769 (15)	−0.0995 (5)	0.0585 (13)
Fe1	0.72165 (11)	0.17982 (3)	0.50931 (10)	0.0325 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.061 (4)	0.035 (4)	0.034 (3)	0.000 (4)	0.006 (3)	−0.003 (3)
C2	0.081 (5)	0.059 (5)	0.048 (5)	0.016 (5)	0.008 (4)	0.023 (4)
C3	0.133 (8)	0.034 (4)	0.047 (5)	0.009 (5)	0.038 (6)	0.007 (4)
C4	0.096 (6)	0.061 (5)	0.029 (4)	−0.050 (5)	0.004 (4)	−0.002 (4)
C5	0.050 (4)	0.052 (4)	0.036 (4)	−0.015 (3)	0.007 (3)	0.002 (3)
C6	0.033 (3)	0.030 (4)	0.040 (4)	−0.005 (3)	0.008 (3)	−0.003 (3)
C7	0.057 (4)	0.031 (4)	0.040 (4)	−0.001 (3)	0.022 (3)	−0.005 (3)
C8	0.065 (4)	0.026 (4)	0.038 (4)	−0.014 (3)	−0.004 (4)	−0.005 (3)
C9	0.030 (3)	0.032 (4)	0.044 (4)	−0.005 (3)	−0.007 (3)	0.002 (3)
C10	0.032 (3)	0.024 (3)	0.027 (3)	0.000 (3)	0.006 (3)	−0.005 (3)
C11	0.015 (3)	0.025 (3)	0.032 (3)	0.001 (2)	0.002 (2)	0.002 (3)
C12	0.015 (3)	0.024 (3)	0.032 (3)	−0.004 (2)	0.001 (3)	−0.003 (3)
C13	0.020 (3)	0.023 (3)	0.026 (3)	−0.002 (3)	−0.002 (2)	0.003 (3)
C14	0.022 (3)	0.030 (4)	0.033 (3)	−0.002 (3)	0.002 (3)	−0.002 (3)
C15	0.032 (4)	0.033 (4)	0.032 (3)	−0.008 (3)	−0.006 (3)	0.001 (3)
C16	0.041 (4)	0.021 (3)	0.026 (3)	0.003 (3)	0.001 (3)	0.000 (2)
C17	0.033 (3)	0.049 (4)	0.035 (4)	0.005 (3)	−0.005 (3)	−0.007 (3)
C18	0.020 (3)	0.035 (4)	0.039 (4)	−0.005 (3)	0.003 (3)	−0.015 (3)
C19	0.025 (3)	0.031 (4)	0.035 (3)	−0.004 (3)	0.001 (3)	−0.007 (3)
N1	0.024 (3)	0.055 (4)	0.073 (4)	0.001 (3)	0.001 (3)	−0.025 (3)
N2	0.061 (4)	0.037 (3)	0.040 (4)	0.012 (3)	−0.007 (3)	−0.004 (3)
O1	0.061 (3)	0.072 (4)	0.073 (4)	0.026 (3)	−0.013 (3)	−0.029 (3)
O2	0.075 (3)	0.041 (3)	0.060 (3)	−0.004 (3)	−0.008 (3)	−0.018 (2)
Fe1	0.0451 (5)	0.0244 (4)	0.0280 (4)	−0.0026 (5)	0.0043 (4)	−0.0007 (4)

Geometric parameters (Å, º) top

C1—C2	1.375 (8)	C8—H8	0.95
C1—C5	1.405 (8)	C9—C10	1.431 (7)
C1—Fe1	2.049 (6)	C9—Fe1	2.028 (5)
C1—H1	0.95	C9—H9	0.95
C2—C3	1.405 (9)	C10—C11	1.427 (7)
C2—Fe1	2.022 (6)	C10—Fe1	2.041 (5)
C2—H2	0.95	C11—C12	1.355 (6)
C3—C4	1.412 (9)	C11—H11	0.95
C3—Fe1	2.024 (7)	C12—C19	1.442 (7)
C3—H3	0.95	C12—C13	1.475 (7)
C4—C5	1.390 (8)	C13—C18	1.388 (7)
C4—Fe1	2.044 (6)	C13—C14	1.405 (6)
C4—H4	0.95	C14—C15	1.383 (7)
C5—Fe1	2.037 (6)	C14—H14	0.95
C5—H5	0.95	C15—C16	1.367 (7)
C6—C7	1.414 (7)	C15—H15	0.95
C6—C10	1.433 (7)	C16—C17	1.386 (7)
C6—Fe1	2.020 (5)	C16—N2	1.493 (7)
C6—H6	0.95	C17—C18	1.381 (7)
C7—C8	1.406 (8)	C17—H17	0.95
C7—Fe1	2.040 (6)	C18—H18	0.95
C7—H7	0.95	C19—N1	1.145 (6)
C8—C9	1.412 (7)	N2—O2	1.222 (6)
C8—Fe1	2.043 (6)	N2—O1	1.224 (6)

C2—C1—C5	107.8 (6)	C18—C13—C12	121.4 (4)
C2—C1—Fe1	69.2 (4)	C14—C13—C12	120.5 (4)
C5—C1—Fe1	69.5 (3)	C15—C14—C13	121.4 (5)
C2—C1—H1	126.1	C15—C14—H14	119.3
C5—C1—H1	126.1	C13—C14—H14	119.3
Fe1—C1—H1	126.8	C16—C15—C14	118.4 (5)
C1—C2—C3	109.3 (7)	C16—C15—H15	120.8
C1—C2—Fe1	71.3 (4)	C14—C15—H15	120.8
C3—C2—Fe1	69.7 (4)	C15—C16—C17	122.2 (5)
C1—C2—H2	125.4	C15—C16—N2	119.9 (5)
C3—C2—H2	125.4	C17—C16—N2	118.0 (5)
Fe1—C2—H2	125.2	C18—C17—C16	118.8 (5)
C2—C3—C4	106.6 (7)	C18—C17—H17	120.6
C2—C3—Fe1	69.6 (4)	C16—C17—H17	120.6
C4—C3—Fe1	70.4 (4)	C17—C18—C13	121.0 (5)
C2—C3—H3	126.7	C17—C18—H18	119.5
C4—C3—H3	126.7	C13—C18—H18	119.5
Fe1—C3—H3	124.8	N1—C19—C12	177.8 (6)
C5—C4—C3	108.2 (6)	O2—N2—O1	125.0 (5)
C5—C4—Fe1	69.9 (4)	O2—N2—C16	117.5 (5)
C3—C4—Fe1	68.9 (4)	O1—N2—C16	117.5 (5)
C5—C4—H4	125.9	C6—Fe1—C2	108.1 (3)
C3—C4—H4	125.9	C6—Fe1—C3	127.8 (3)
Fe1—C4—H4	126.9	C2—Fe1—C3	40.7 (3)
C4—C5—C1	108.1 (6)	C6—Fe1—C9	68.8 (2)
C4—C5—Fe1	70.3 (4)	C2—Fe1—C9	169.1 (3)
C1—C5—Fe1	70.3 (3)	C3—Fe1—C9	149.4 (3)
C4—C5—H5	125.9	C6—Fe1—C5	151.8 (2)
C1—C5—H5	125.9	C2—Fe1—C5	67.2 (3)
Fe1—C5—H5	125	C3—Fe1—C5	67.9 (3)
C7—C6—C10	108.4 (5)	C9—Fe1—C5	110.3 (2)
C7—C6—Fe1	70.4 (3)	C6—Fe1—C7	40.8 (2)
C10—C6—Fe1	70.1 (3)	C2—Fe1—C7	116.9 (3)
C7—C6—H6	125.8	C3—Fe1—C7	106.5 (3)
C10—C6—H6	125.8	C9—Fe1—C7	68.1 (2)
Fe1—C6—H6	125.3	C5—Fe1—C7	167.0 (2)
C8—C7—C6	108.5 (5)	C6—Fe1—C10	41.30 (19)
C8—C7—Fe1	70.0 (3)	C2—Fe1—C10	129.8 (3)
C6—C7—Fe1	68.9 (3)	C3—Fe1—C10	167.4 (3)
C8—C7—H7	125.7	C9—Fe1—C10	41.16 (19)
C6—C7—H7	125.7	C5—Fe1—C10	119.0 (2)
Fe1—C7—H7	127	C7—Fe1—C10	68.9 (2)
C7—C8—C9	107.9 (5)	C6—Fe1—C8	68.6 (2)
C7—C8—Fe1	69.8 (3)	C2—Fe1—C8	149.2 (3)
C9—C8—Fe1	69.1 (3)	C3—Fe1—C8	115.7 (3)
C7—C8—H8	126.1	C9—Fe1—C8	40.6 (2)
C9—C8—H8	126.1	C5—Fe1—C8	130.2 (3)
Fe1—C8—H8	126.6	C7—Fe1—C8	40.3 (2)
C8—C9—C10	109.0 (5)	C10—Fe1—C8	69.1 (2)
C8—C9—Fe1	70.3 (3)	C6—Fe1—C4	166.5 (3)
C10—C9—Fe1	69.9 (3)	C2—Fe1—C4	67.5 (3)
C8—C9—H9	125.5	C3—Fe1—C4	40.6 (3)
C10—C9—H9	125.5	C9—Fe1—C4	117.9 (3)
Fe1—C9—H9	125.9	C5—Fe1—C4	39.8 (2)
C11—C10—C9	122.6 (5)	C7—Fe1—C4	128.5 (3)
C11—C10—C6	131.3 (5)	C10—Fe1—C4	151.2 (3)
C9—C10—C6	106.1 (4)	C8—Fe1—C4	108.2 (2)
C11—C10—Fe1	126.2 (4)	C6—Fe1—C1	118.2 (2)
C9—C10—Fe1	68.9 (3)	C2—Fe1—C1	39.5 (2)
C6—C10—Fe1	68.6 (3)	C3—Fe1—C1	67.7 (3)
C12—C11—C10	130.5 (5)	C9—Fe1—C1	131.9 (2)
C12—C11—H11	114.7	C5—Fe1—C1	40.2 (2)
C10—C11—H11	114.7	C7—Fe1—C1	150.2 (3)
C11—C12—C19	118.9 (5)	C10—Fe1—C1	110.0 (2)
C11—C12—C13	125.1 (4)	C8—Fe1—C1	169.3 (2)
C19—C12—C13	115.9 (4)	C4—Fe1—C1	67.1 (2)
C18—C13—C14	118.1 (5)

C5—C1—C2—C3	0.7 (7)	C10—C9—Fe1—C5	−111.2 (3)
Fe1—C1—C2—C3	59.6 (5)	C8—C9—Fe1—C7	−37.4 (3)
C5—C1—C2—Fe1	−58.9 (4)	C10—C9—Fe1—C7	82.6 (3)
C1—C2—C3—C4	0.5 (8)	C8—C9—Fe1—C10	−120.0 (5)
Fe1—C2—C3—C4	61.1 (5)	C10—C9—Fe1—C8	120.0 (5)
C1—C2—C3—Fe1	−60.6 (5)	C8—C9—Fe1—C4	85.8 (4)
C2—C3—C4—C5	−1.6 (7)	C10—C9—Fe1—C4	−154.3 (3)
Fe1—C3—C4—C5	59.0 (4)	C8—C9—Fe1—C1	169.1 (3)
C2—C3—C4—Fe1	−60.6 (5)	C10—C9—Fe1—C1	−70.9 (4)
C3—C4—C5—C1	2.0 (7)	C4—C5—Fe1—C6	167.6 (5)
Fe1—C4—C5—C1	60.4 (4)	C1—C5—Fe1—C6	48.9 (7)
C3—C4—C5—Fe1	−58.4 (5)	C4—C5—Fe1—C2	81.7 (5)
C2—C1—C5—C4	−1.7 (7)	C1—C5—Fe1—C2	−36.9 (4)
Fe1—C1—C5—C4	−60.4 (4)	C4—C5—Fe1—C3	37.6 (4)
C2—C1—C5—Fe1	58.8 (4)	C1—C5—Fe1—C3	−81.0 (4)
C10—C6—C7—C8	1.2 (6)	C4—C5—Fe1—C9	−109.7 (5)
Fe1—C6—C7—C8	−58.9 (4)	C1—C5—Fe1—C9	131.7 (4)
C10—C6—C7—Fe1	60.1 (4)	C4—C5—Fe1—C7	−29.4 (14)
C6—C7—C8—C9	−0.7 (7)	C1—C5—Fe1—C7	−148.0 (10)
Fe1—C7—C8—C9	−58.8 (4)	C4—C5—Fe1—C10	−154.2 (4)
C6—C7—C8—Fe1	58.2 (4)	C1—C5—Fe1—C10	87.2 (4)
C7—C8—C9—C10	−0.1 (6)	C4—C5—Fe1—C8	−68.1 (5)
Fe1—C8—C9—C10	−59.4 (4)	C1—C5—Fe1—C8	173.3 (4)
C7—C8—C9—Fe1	59.2 (4)	C1—C5—Fe1—C4	−118.6 (6)
C8—C9—C10—C11	179.9 (5)	C4—C5—Fe1—C1	118.6 (6)
Fe1—C9—C10—C11	120.3 (5)	C8—C7—Fe1—C6	120.3 (5)
C8—C9—C10—C6	0.9 (6)	C8—C7—Fe1—C2	−152.9 (4)
Fe1—C9—C10—C6	−58.7 (4)	C6—C7—Fe1—C2	86.8 (4)
C8—C9—C10—Fe1	59.6 (4)	C8—C7—Fe1—C3	−110.4 (4)
C7—C6—C10—C11	179.8 (5)	C6—C7—Fe1—C3	129.3 (4)
Fe1—C6—C10—C11	−119.9 (6)	C8—C7—Fe1—C9	37.7 (3)
C7—C6—C10—C9	−1.3 (6)	C6—C7—Fe1—C9	−82.6 (4)
Fe1—C6—C10—C9	58.9 (4)	C8—C7—Fe1—C5	−47.6 (13)
C7—C6—C10—Fe1	−60.2 (4)	C6—C7—Fe1—C5	−167.8 (10)
C9—C10—C11—C12	165.5 (5)	C8—C7—Fe1—C10	82.1 (4)
C6—C10—C11—C12	−15.8 (10)	C6—C7—Fe1—C10	−38.2 (3)
Fe1—C10—C11—C12	−108.0 (6)	C6—C7—Fe1—C8	−120.3 (5)
C10—C11—C12—C19	−0.2 (9)	C8—C7—Fe1—C4	−71.3 (5)
C10—C11—C12—C13	−178.3 (5)	C6—C7—Fe1—C4	168.5 (4)
C11—C12—C13—C18	−7.7 (8)	C8—C7—Fe1—C1	175.8 (4)
C19—C12—C13—C18	174.0 (5)	C6—C7—Fe1—C1	55.6 (6)
C11—C12—C13—C14	169.4 (5)	C11—C10—Fe1—C6	126.2 (6)
C19—C12—C13—C14	−8.8 (7)	C9—C10—Fe1—C6	−118.1 (4)
C18—C13—C14—C15	0.1 (8)	C11—C10—Fe1—C2	55.9 (6)
C12—C13—C14—C15	−177.1 (5)	C9—C10—Fe1—C2	171.5 (4)
C13—C14—C15—C16	1.6 (8)	C6—C10—Fe1—C2	−70.4 (4)
C14—C15—C16—C17	−1.6 (8)	C11—C10—Fe1—C3	92.9 (12)
C14—C15—C16—N2	178.0 (5)	C9—C10—Fe1—C3	−151.5 (11)
C15—C16—C17—C18	0.1 (8)	C6—C10—Fe1—C3	−33.3 (13)
N2—C16—C17—C18	−179.6 (5)	C11—C10—Fe1—C9	−115.7 (6)
C16—C17—C18—C13	1.6 (8)	C6—C10—Fe1—C9	118.1 (4)
C14—C13—C18—C17	−1.7 (8)	C11—C10—Fe1—C5	−27.5 (5)
C12—C13—C18—C17	175.5 (5)	C9—C10—Fe1—C5	88.2 (4)
C11—C12—C19—N1	−154 (17)	C6—C10—Fe1—C5	−153.7 (3)
C13—C12—C19—N1	24 (17)	C11—C10—Fe1—C7	163.9 (5)
C15—C16—N2—O2	6.5 (7)	C9—C10—Fe1—C7	−80.4 (3)
C17—C16—N2—O2	−173.8 (5)	C6—C10—Fe1—C7	37.7 (3)
C15—C16—N2—O1	−172.8 (5)	C11—C10—Fe1—C8	−152.8 (5)
C17—C16—N2—O1	6.9 (7)	C9—C10—Fe1—C8	−37.1 (3)
C7—C6—Fe1—C2	−110.5 (4)	C6—C10—Fe1—C8	81.0 (3)
C10—C6—Fe1—C2	130.4 (4)	C11—C10—Fe1—C4	−62.8 (7)
C7—C6—Fe1—C3	−69.7 (5)	C9—C10—Fe1—C4	52.8 (6)
C10—C6—Fe1—C3	171.2 (4)	C6—C10—Fe1—C4	170.9 (5)
C7—C6—Fe1—C9	80.6 (4)	C11—C10—Fe1—C1	15.8 (5)
C10—C6—Fe1—C9	−38.5 (3)	C9—C10—Fe1—C1	131.5 (3)
C7—C6—Fe1—C5	174.2 (5)	C6—C10—Fe1—C1	−110.4 (3)
C10—C6—Fe1—C5	55.2 (6)	C7—C8—Fe1—C6	−37.3 (3)
C10—C6—Fe1—C7	−119.1 (5)	C9—C8—Fe1—C6	82.1 (3)
C7—C6—Fe1—C10	119.1 (5)	C7—C8—Fe1—C2	52.3 (7)
C7—C6—Fe1—C8	36.9 (3)	C9—C8—Fe1—C2	171.7 (5)
C10—C6—Fe1—C8	−82.2 (3)	C7—C8—Fe1—C3	85.5 (4)
C7—C6—Fe1—C4	−42.0 (12)	C9—C8—Fe1—C3	−155.2 (4)
C10—C6—Fe1—C4	−161.0 (10)	C7—C8—Fe1—C9	−119.4 (5)
C7—C6—Fe1—C1	−152.2 (4)	C7—C8—Fe1—C5	167.4 (4)
C10—C6—Fe1—C1	88.7 (4)	C9—C8—Fe1—C5	−73.2 (4)
C1—C2—Fe1—C6	−112.7 (4)	C9—C8—Fe1—C7	119.4 (5)
C3—C2—Fe1—C6	127.5 (4)	C7—C8—Fe1—C10	−81.7 (4)
C1—C2—Fe1—C3	119.8 (6)	C9—C8—Fe1—C10	37.6 (3)
C1—C2—Fe1—C9	−41.0 (16)	C7—C8—Fe1—C4	128.7 (4)
C3—C2—Fe1—C9	−160.7 (13)	C9—C8—Fe1—C4	−111.9 (4)
C1—C2—Fe1—C5	37.6 (4)	C7—C8—Fe1—C1	−168.7 (12)
C3—C2—Fe1—C5	−82.2 (4)	C9—C8—Fe1—C1	−49.4 (14)
C1—C2—Fe1—C7	−156.0 (4)	C5—C4—Fe1—C6	−154.2 (9)
C3—C2—Fe1—C7	84.2 (5)	C3—C4—Fe1—C6	−34.4 (13)
C1—C2—Fe1—C10	−71.9 (5)	C5—C4—Fe1—C2	−80.9 (4)
C3—C2—Fe1—C10	168.3 (4)	C3—C4—Fe1—C2	38.9 (4)
C1—C2—Fe1—C8	168.9 (4)	C5—C4—Fe1—C3	−119.8 (6)
C3—C2—Fe1—C8	49.2 (7)	C5—C4—Fe1—C9	88.7 (4)
C1—C2—Fe1—C4	80.9 (4)	C3—C4—Fe1—C9	−151.5 (4)
C3—C2—Fe1—C4	−38.9 (4)	C3—C4—Fe1—C5	119.8 (6)
C3—C2—Fe1—C1	−119.8 (6)	C5—C4—Fe1—C7	171.9 (4)
C2—C3—Fe1—C6	−72.6 (5)	C3—C4—Fe1—C7	−68.3 (5)
C4—C3—Fe1—C6	170.4 (4)	C5—C4—Fe1—C10	52.3 (7)
C4—C3—Fe1—C2	−117.0 (6)	C3—C4—Fe1—C10	172.1 (5)
C2—C3—Fe1—C9	173.0 (5)	C5—C4—Fe1—C8	131.7 (4)
C4—C3—Fe1—C9	55.9 (7)	C3—C4—Fe1—C8	−108.4 (4)
C2—C3—Fe1—C5	80.2 (4)	C5—C4—Fe1—C1	−38.0 (4)
C4—C3—Fe1—C5	−36.8 (4)	C3—C4—Fe1—C1	81.8 (4)
C2—C3—Fe1—C7	−112.3 (5)	C2—C1—Fe1—C6	84.4 (5)
C4—C3—Fe1—C7	130.7 (4)	C5—C1—Fe1—C6	−156.2 (4)
C2—C3—Fe1—C10	−45.3 (13)	C5—C1—Fe1—C2	119.5 (6)
C4—C3—Fe1—C10	−162.3 (10)	C2—C1—Fe1—C3	−37.7 (4)
C2—C3—Fe1—C8	−154.5 (4)	C5—C1—Fe1—C3	81.8 (4)
C4—C3—Fe1—C8	88.4 (4)	C2—C1—Fe1—C9	170.4 (4)
C2—C3—Fe1—C4	117.0 (6)	C5—C1—Fe1—C9	−70.1 (5)
C2—C3—Fe1—C1	36.6 (4)	C2—C1—Fe1—C5	−119.5 (6)
C4—C3—Fe1—C1	−80.4 (4)	C2—C1—Fe1—C7	46.7 (7)
C8—C9—Fe1—C6	−81.4 (4)	C5—C1—Fe1—C7	166.2 (5)
C10—C9—Fe1—C6	38.6 (3)	C2—C1—Fe1—C10	129.0 (4)
C8—C9—Fe1—C2	−156.9 (13)	C5—C1—Fe1—C10	−111.6 (4)
C10—C9—Fe1—C2	−36.9 (15)	C2—C1—Fe1—C8	−148.0 (12)
C8—C9—Fe1—C3	48.1 (6)	C5—C1—Fe1—C8	−28.6 (15)
C10—C9—Fe1—C3	168.1 (5)	C2—C1—Fe1—C4	−81.9 (5)
C8—C9—Fe1—C5	128.8 (4)	C5—C1—Fe1—C4	37.6 (4)

Experimental details

Crystal data
Chemical formula	[Fe(C₅H₅)(C₁₄H₉N₂O₂)]
M_r	358.17
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	173
a, b, c (Å)	6.7186 (14), 28.036 (6), 8.4165 (18)
β (°)	90.108 (6)
V (Å³)	1585.3 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.96
Crystal size (mm)	0.53 × 0.05 × 0.02

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.629, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections	9108, 2672, 1437
R_int	0.112
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.114, 0.90
No. of reflections	2672
No. of parameters	218
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.65

Computer programs: APEX2 (Bruker, 2005), SAINT-Plus (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

We thank Dr Manuel Fernandez for the data collection, Dr Benard Owaga for advice during the preparation of the manuscript and the University of KwaZulu-Natal and the NRF for financial support.

References

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