(Z)-1-Ferrocenyl-3-hydroxy-3-(2-pyrid­yl)prop-2-en-1-one

Shi, Y.-C.; Cheng, H.-J.

doi:10.1107/S1600536805030102

(Z)-1-Ferrocenyl-3-hydroxy-3-(2-pyridyl)prop-2-en-1-one

The title compound, [Fe(C₅H₅)(C₁₃H₁₀NO₂)], has been synthesized by the Claisen condensation reaction of acetylferrocene and ethyl picolinate in the presence of sodium ethoxide. The enone structure is stabilized by a strong [OH

O=C] intramolecular hydrogen bond.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805030102/ng6204sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805030102/ng6204Isup2.hkl Contains datablock I

CCDC reference: 287671

checkCIF report

Key indicators

Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.007 Å
R factor = 0.039
wR factor = 0.130
Data-to-parameter ratio = 12.9

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT027_ALERT_3_B _diffrn_reflns_theta_full (too) Low ............      24.98 Deg.

Alert level C
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C2
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         Fe
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

Enaminones are important ligands in coordination chemistry (Doherty et al., 1999; Kim et al., 2001; Li et al., 2004). In continuation of our investigation of the chemistry of ferrocenyl enaminones, we have prepared the title compound, (I), as an intermediate, via the Claisen condensation of acetylferrocene and ethyl picolinate (Shi et al., 2004, 2005).

Ccompound (I) has been shown by ¹H NMR spectroscopy to exist in solution in the enol and not the keto form. IR spectroscopy shows only the enol form in the solid state; this has been further confirmed in the present study of its crystal structure (Fig. 1).

As also noted in the related compound 1-ferrocenyl-3-hydroxylbut-2-en-1-one, (II) (Bell et al., 1992), the O═C—C═C—O fragment of the molecule of (I) is planar. The bond lengths indicate electron delocalization (Gilli et al., 2000). The O═C—C═C—O plane is twisted with respect to the pyridyl and cyclopentadienyl rings by 3.3 (2) and 9.4 (2)°, respectively. The two cyclopentadienyl rings in the ferrocenyl group are parallel [dihedral angle 1.5 (3)°] and adopt a staggered conformation. The C13—C14 bond, which is typical of a single bond (Csp²—Csp²), suggests that the pyridyl ring is not involved in the conjugation of the O═C—C═C—O moiety.

Unlike (II), as well as the intramolecular hydrogen bond [O—H···O═C], intermolecular hydrogen bonds [C—H···O═C] are also present in the crystal structure of (I) (Fig. 2, Table 2).

Experimental top

The title compound was synthesized by refluxing a tetrahydrofuran solution of acetylferrocene and ethyl picolinate in the presence of sodium ethoxide (1:1:1) for 4 h, as described previously (Reference?). Red crystals of (I) were obtained by slow evaporation from a CH₂Cl₂–petroleum ether (Ratio?) solution (m.p. 417.6–418.4 K). Spectroscopic analysis: IR (KBr, ν, cm⁻¹): 3438.84 (m, OH), 3101.12 (s, CH), 1593.7 (vs, O═C), 1546.10 (vs, C═C); ¹H NMR (600 MHz, CDCl₃, δ, p.p.m.): 16.254 (1H, s, OH), 8.731, 8.149, 7.881, 7.440 (4H, 4m, pyridyl), 7.098 (1H, s, CH), 4.993, 4.599 (2H, 2H, 2m, C₅H₄), 4.246 (5H, s, C₅H₅).

Computing details top

Data collection: CAD-4 Software(Enraf–Nonius,1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo,1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.

Figures top

	Fig. 1. The molecular structure of (I). Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. A packing diagram for (I). Dashed lines indicate hydrogen bonds.

(Z)-1-Ferrocenyl-3-hydroxyl-3-[(2-pyridyl)]prop-2-en-1-one top

Crystal data top

[Fe(C₅H₅)(C₁₃H₁₀NO₂)]	F(000) = 688
M_r = 333.16	D_x = 1.509 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.547 (2) Å	Cell parameters from 25 reflections
b = 12.804 (3) Å	θ = 10–13°
c = 11.195 (2) Å	µ = 1.03 mm⁻¹
β = 104.08 (3)°	T = 295 K
V = 1466.4 (5) Å³	Block, red
Z = 4	0.4 × 0.2 × 0.1 mm

Data collection top

Enraf–Nonius CAD4 diffractometer	1949 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.045
Graphite monochromator	θ_max = 25.0°, θ_min = 2.0°
ω/2θ scans	h = 0→12
Absorption correction: empirical (using intensity measurements) via ψ scan (North et al., 1968)	k = 0→15
T_min = 0.773, T_max = 0.901	l = −13→12
2721 measured reflections	3 standard reflections every 200 reflections
2577 independent reflections	intensity decay: 0.1%

Refinement top

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)] = 0.039	H-atom parameters constrained
wR(F²) = 0.130	w = 1/[σ²(F_o²) + (0.0533P)² + 1.5624P] where P = (F_o² + 2F_c²)/3
S = 1.10	(Δ/σ)_max = 0.001
2577 reflections	Δρ_max = 0.44 e Å⁻³
200 parameters	Δρ_min = −0.32 e Å⁻³
6 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0118 (16)

Crystal data top

[Fe(C₅H₅)(C₁₃H₁₀NO₂)]	V = 1466.4 (5) Å³
M_r = 333.16	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.547 (2) Å	µ = 1.03 mm⁻¹
b = 12.804 (3) Å	T = 295 K
c = 11.195 (2) Å	0.4 × 0.2 × 0.1 mm
β = 104.08 (3)°

Data collection top

Enraf–Nonius CAD4 diffractometer	1949 reflections with I > 2σ(I)
Absorption correction: empirical (using intensity measurements) via ψ scan (North et al., 1968)	R_int = 0.045
T_min = 0.773, T_max = 0.901	3 standard reflections every 200 reflections
2721 measured reflections	intensity decay: 0.1%
2577 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	6 restraints
wR(F²) = 0.130	H-atom parameters constrained
S = 1.10	Δρ_max = 0.44 e Å⁻³
2577 reflections	Δρ_min = −0.32 e Å⁻³
200 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.

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

	x	y	z	U_iso*/U_eq
Fe	0.13150 (5)	0.36429 (4)	0.22403 (5)	0.0429 (2)
O1	0.1953 (3)	0.5468 (2)	0.4846 (3)	0.0687 (9)
O2	0.2936 (3)	0.5039 (2)	0.7051 (3)	0.0685 (9)
H2O	0.2439	0.5317	0.6458	0.103*
N	0.5505 (3)	0.3205 (3)	0.7292 (3)	0.0497 (8)
C1	0.0629 (5)	0.2159 (4)	0.1862 (6)	0.0794 (16)
H1	0.1039	0.1603	0.1486	0.095*
C2	0.0854 (6)	0.2382 (5)	0.3135 (6)	0.094 (2)
H2	0.1444	0.2002	0.3806	0.113*
C3	0.0055 (6)	0.3236 (5)	0.3263 (5)	0.0831 (18)
H3	−0.0007	0.3559	0.4041	0.100*
C4	−0.0658 (4)	0.3515 (4)	0.2096 (5)	0.0675 (13)
H4	−0.1293	0.4087	0.1906	0.081*
C5	−0.0297 (4)	0.2876 (4)	0.1246 (5)	0.0685 (14)
H5	−0.0637	0.2917	0.0351	0.082*
C6	0.1893 (5)	0.4713 (4)	0.1117 (4)	0.0658 (13)
H6	0.1400	0.4907	0.0287	0.079*
C7	0.1765 (4)	0.5182 (4)	0.2228 (4)	0.0593 (12)
H7	0.1188	0.5766	0.2301	0.071*
C8	0.2640 (4)	0.4653 (3)	0.3225 (4)	0.0470 (10)
C9	0.3282 (4)	0.3865 (4)	0.2704 (4)	0.0516 (10)
H9	0.3931	0.3373	0.3165	0.062*
C10	0.2820 (4)	0.3902 (4)	0.1407 (4)	0.0641 (13)
H10	0.3086	0.3438	0.0816	0.077*
C11	0.2752 (4)	0.4821 (3)	0.4527 (4)	0.0474 (9)
C12	0.3672 (4)	0.4277 (3)	0.5448 (4)	0.0453 (9)
H12	0.4252	0.3818	0.5216	0.054*
C13	0.3725 (4)	0.4412 (3)	0.6665 (4)	0.0477 (10)
C14	0.4659 (4)	0.3844 (3)	0.7660 (4)	0.0430 (9)
C15	0.4637 (4)	0.3953 (3)	0.8882 (4)	0.0555 (11)
H15	0.4039	0.4402	0.9103	0.067*
C16	0.5502 (5)	0.3395 (4)	0.9772 (4)	0.0599 (12)
H16	0.5504	0.3464	1.0599	0.072*
C17	0.6362 (4)	0.2733 (4)	0.9410 (4)	0.0577 (11)
H17	0.6946	0.2331	0.9984	0.069*
C18	0.6339 (4)	0.2680 (4)	0.8169 (4)	0.0590 (11)
H18	0.6945	0.2249	0.7934	0.071*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe	0.0391 (3)	0.0488 (4)	0.0411 (3)	−0.0027 (2)	0.0105 (2)	0.0049 (3)
O1	0.076 (2)	0.0532 (19)	0.072 (2)	0.0291 (16)	0.0094 (17)	−0.0068 (16)
O2	0.083 (2)	0.061 (2)	0.063 (2)	0.0251 (17)	0.0201 (17)	−0.0087 (16)
N	0.0475 (19)	0.0514 (19)	0.051 (2)	0.0008 (16)	0.0138 (16)	−0.0006 (16)
C1	0.073 (3)	0.052 (3)	0.114 (5)	−0.013 (3)	0.024 (3)	−0.011 (3)
C2	0.081 (4)	0.088 (4)	0.100 (4)	−0.028 (3)	−0.005 (3)	0.046 (3)
C3	0.088 (4)	0.107 (5)	0.064 (3)	−0.043 (4)	0.037 (3)	−0.009 (3)
C4	0.049 (3)	0.088 (4)	0.074 (3)	−0.010 (2)	0.031 (2)	−0.006 (3)
C5	0.048 (3)	0.087 (4)	0.068 (3)	−0.011 (3)	0.010 (2)	−0.026 (3)
C6	0.067 (3)	0.081 (3)	0.048 (3)	−0.012 (3)	0.011 (2)	0.021 (2)
C7	0.055 (2)	0.046 (2)	0.076 (3)	−0.003 (2)	0.015 (2)	0.023 (2)
C8	0.041 (2)	0.042 (2)	0.056 (2)	−0.0081 (17)	0.0070 (18)	0.0024 (18)
C9	0.038 (2)	0.066 (3)	0.052 (2)	−0.0005 (19)	0.0130 (18)	0.004 (2)
C10	0.053 (3)	0.093 (4)	0.051 (3)	−0.007 (3)	0.023 (2)	0.006 (2)
C11	0.048 (2)	0.0346 (19)	0.058 (3)	−0.0023 (17)	0.0099 (19)	0.0016 (18)
C12	0.045 (2)	0.042 (2)	0.047 (2)	0.0026 (17)	0.0071 (17)	−0.0024 (17)
C13	0.049 (2)	0.035 (2)	0.061 (3)	−0.0008 (17)	0.0156 (19)	−0.0059 (18)
C14	0.045 (2)	0.036 (2)	0.047 (2)	−0.0074 (16)	0.0103 (17)	−0.0043 (16)
C15	0.065 (3)	0.049 (2)	0.055 (3)	−0.005 (2)	0.018 (2)	−0.006 (2)
C16	0.070 (3)	0.062 (3)	0.046 (2)	−0.008 (2)	0.011 (2)	0.002 (2)
C17	0.048 (2)	0.059 (3)	0.062 (3)	−0.007 (2)	0.004 (2)	0.008 (2)
C18	0.046 (2)	0.059 (3)	0.067 (3)	0.002 (2)	0.006 (2)	−0.001 (2)

Geometric parameters (Å, º) top

Fe—C2	2.021 (5)	C5—H5	0.9800
Fe—C3	2.022 (5)	C6—C10	1.409 (7)
Fe—C8	2.022 (4)	C6—C7	1.417 (7)
Fe—C7	2.027 (4)	C6—H6	0.9800
Fe—C9	2.032 (4)	C7—C8	1.434 (6)
Fe—C1	2.040 (5)	C7—H7	0.9800
Fe—C5	2.043 (4)	C8—C9	1.417 (6)
Fe—C6	2.050 (4)	C8—C11	1.450 (6)
Fe—C10	2.055 (4)	C9—C10	1.416 (6)
Fe—C4	2.055 (4)	C9—H9	0.9800
O1—C11	1.293 (5)	C10—H10	0.9800
O2—C13	1.303 (5)	C11—C12	1.415 (5)
O2—H2O	0.8200	C12—C13	1.361 (6)
N—C18	1.330 (5)	C12—H12	0.9300
N—C14	1.347 (5)	C13—C14	1.484 (6)
C1—C5	1.394 (7)	C14—C15	1.382 (6)
C1—C2	1.416 (9)	C15—C16	1.376 (6)
C1—H1	0.9800	C15—H15	0.9300
C2—C3	1.408 (9)	C16—C17	1.372 (6)
C2—H2	0.9800	C16—H16	0.9300
C3—C4	1.387 (8)	C17—C18	1.385 (6)
C3—H3	0.9800	C17—H17	0.9300
C4—C5	1.378 (7)	C18—H18	0.9300
C4—H4	0.9800

C2—Fe—C3	40.8 (3)	C5—C4—Fe	69.9 (3)
C2—Fe—C8	117.3 (2)	C3—C4—Fe	68.9 (3)
C3—Fe—C8	108.5 (2)	C5—C4—H4	125.7
C2—Fe—C7	149.8 (3)	C3—C4—H4	125.7
C3—Fe—C7	116.2 (2)	Fe—C4—H4	125.7
C8—Fe—C7	41.46 (17)	C4—C5—C1	109.2 (5)
C2—Fe—C9	109.8 (2)	C4—C5—Fe	70.8 (3)
C3—Fe—C9	131.4 (2)	C1—C5—Fe	69.9 (3)
C8—Fe—C9	40.92 (17)	C4—C5—H5	125.4
C7—Fe—C9	68.89 (18)	C1—C5—H5	125.4
C2—Fe—C1	40.8 (3)	Fe—C5—H5	125.4
C3—Fe—C1	68.2 (2)	C10—C6—C7	108.6 (4)
C8—Fe—C1	150.6 (2)	C10—C6—Fe	70.1 (3)
C7—Fe—C1	167.2 (2)	C7—C6—Fe	68.8 (2)
C9—Fe—C1	118.1 (2)	C10—C6—H6	125.7
C2—Fe—C5	67.5 (2)	C7—C6—H6	125.7
C3—Fe—C5	67.1 (2)	Fe—C6—H6	125.7
C8—Fe—C5	167.82 (19)	C6—C7—C8	107.6 (4)
C7—Fe—C5	129.0 (2)	C6—C7—Fe	70.5 (3)
C9—Fe—C5	150.33 (19)	C8—C7—Fe	69.1 (2)
C1—Fe—C5	39.9 (2)	C6—C7—H7	126.2
C2—Fe—C6	168.9 (3)	C8—C7—H7	126.2
C3—Fe—C6	148.7 (3)	Fe—C7—H7	126.2
C8—Fe—C6	68.79 (18)	C9—C8—C7	107.3 (4)
C7—Fe—C6	40.7 (2)	C9—C8—C11	126.1 (4)
C9—Fe—C6	68.04 (18)	C7—C8—C11	126.3 (4)
C1—Fe—C6	129.7 (2)	C9—C8—Fe	69.9 (2)
C5—Fe—C6	108.6 (2)	C7—C8—Fe	69.5 (2)
C2—Fe—C10	131.3 (3)	C11—C8—Fe	121.3 (3)
C3—Fe—C10	170.2 (2)	C10—C9—C8	108.6 (4)
C8—Fe—C10	68.69 (19)	C10—C9—Fe	70.6 (2)
C7—Fe—C10	68.4 (2)	C8—C9—Fe	69.2 (2)
C9—Fe—C10	40.54 (17)	C10—C9—H9	125.7
C1—Fe—C10	109.3 (2)	C8—C9—H9	125.7
C5—Fe—C10	117.6 (2)	Fe—C9—H9	125.7
C6—Fe—C10	40.1 (2)	C6—C10—C9	107.9 (4)
C2—Fe—C4	67.3 (2)	C6—C10—Fe	69.8 (3)
C3—Fe—C4	39.8 (2)	C9—C10—Fe	68.9 (2)
C8—Fe—C4	130.24 (19)	C6—C10—H10	126.0
C7—Fe—C4	108.1 (2)	C9—C10—H10	126.0
C9—Fe—C4	169.37 (18)	Fe—C10—H10	126.0
C1—Fe—C4	67.0 (2)	O1—C11—C8	118.3 (4)
C5—Fe—C4	39.30 (19)	O1—C11—C12	119.5 (4)
C6—Fe—C4	116.8 (2)	C8—C11—C12	122.2 (4)
C10—Fe—C4	149.0 (2)	C11—C12—C13	121.4 (4)
C13—O2—H2O	109.5	C13—C12—H12	119.3
C18—N—C14	116.7 (4)	C11—C12—H12	119.3
C5—C1—C2	106.9 (5)	O2—C13—C12	122.4 (4)
C5—C1—Fe	70.2 (3)	O2—C13—C14	114.5 (4)
C2—C1—Fe	68.9 (3)	C12—C13—C14	123.2 (4)
C5—C1—H1	126.5	N—C14—C15	122.5 (4)
C2—C1—H1	126.5	N—C14—C13	115.9 (3)
Fe—C1—H1	126.5	C15—C14—C13	121.7 (4)
C3—C2—C1	107.5 (5)	C16—C15—C14	119.7 (4)
C3—C2—Fe	69.7 (3)	C16—C15—H15	120.1
C1—C2—Fe	70.3 (3)	C14—C15—H15	120.1
C3—C2—H2	126.2	C17—C16—C15	118.5 (4)
C1—C2—H2	126.2	C17—C16—H16	120.8
Fe—C2—H2	126.2	C15—C16—H16	120.8
C4—C3—C2	107.8 (5)	C16—C17—C18	118.3 (4)
C4—C3—Fe	71.4 (3)	C16—C17—H17	120.8
C2—C3—Fe	69.6 (3)	C18—C17—H17	120.8
C4—C3—H3	126.1	N—C18—C17	124.3 (4)
C2—C3—H3	126.1	N—C18—H18	117.9
Fe—C3—H3	126.1	C17—C18—H18	117.9
C5—C4—C3	108.6 (5)

C2—Fe—C1—C5	118.1 (5)	C10—C6—C7—Fe	−59.0 (3)
C3—Fe—C1—C5	79.8 (4)	C2—Fe—C7—C6	173.8 (4)
C8—Fe—C1—C5	169.2 (3)	C3—Fe—C7—C6	−152.6 (3)
C7—Fe—C1—C5	−33.0 (11)	C8—Fe—C7—C6	118.6 (4)
C9—Fe—C1—C5	−153.7 (3)	C9—Fe—C7—C6	80.5 (3)
C6—Fe—C1—C5	−69.9 (4)	C1—Fe—C7—C6	−45.2 (10)
C10—Fe—C1—C5	−110.2 (3)	C5—Fe—C7—C6	−71.9 (4)
C4—Fe—C1—C5	36.7 (3)	C10—Fe—C7—C6	36.8 (3)
C3—Fe—C1—C2	−38.3 (4)	C4—Fe—C7—C6	−110.4 (3)
C8—Fe—C1—C2	51.1 (6)	C2—Fe—C7—C8	55.2 (5)
C7—Fe—C1—C2	−151.1 (9)	C3—Fe—C7—C8	88.8 (3)
C9—Fe—C1—C2	88.2 (4)	C9—Fe—C7—C8	−38.2 (2)
C5—Fe—C1—C2	−118.1 (5)	C1—Fe—C7—C8	−163.8 (9)
C6—Fe—C1—C2	172.0 (4)	C5—Fe—C7—C8	169.5 (3)
C10—Fe—C1—C2	131.7 (4)	C6—Fe—C7—C8	−118.6 (4)
C4—Fe—C1—C2	−81.4 (4)	C10—Fe—C7—C8	−81.8 (3)
C5—C1—C2—C3	−0.2 (6)	C4—Fe—C7—C8	131.0 (3)
Fe—C1—C2—C3	60.0 (4)	C6—C7—C8—C9	−0.3 (5)
C5—C1—C2—Fe	−60.1 (4)	Fe—C7—C8—C9	59.9 (3)
C8—Fe—C2—C3	87.1 (4)	C6—C7—C8—C11	−174.7 (4)
C7—Fe—C2—C3	49.4 (6)	Fe—C7—C8—C11	−114.4 (4)
C9—Fe—C2—C3	131.3 (3)	C6—C7—C8—Fe	−60.3 (3)
C1—Fe—C2—C3	−118.3 (5)	C2—Fe—C8—C9	89.3 (4)
C5—Fe—C2—C3	−80.5 (4)	C3—Fe—C8—C9	132.7 (3)
C6—Fe—C2—C3	−152.0 (10)	C7—Fe—C8—C9	−118.4 (4)
C10—Fe—C2—C3	171.9 (3)	C1—Fe—C8—C9	54.4 (5)
C4—Fe—C2—C3	−37.8 (3)	C5—Fe—C8—C9	−160.5 (9)
C3—Fe—C2—C1	118.3 (5)	C6—Fe—C8—C9	−80.5 (3)
C8—Fe—C2—C1	−154.6 (3)	C10—Fe—C8—C9	−37.3 (3)
C7—Fe—C2—C1	167.7 (4)	C4—Fe—C8—C9	171.7 (3)
C9—Fe—C2—C1	−110.5 (3)	C2—Fe—C8—C7	−152.3 (3)
C5—Fe—C2—C1	37.8 (3)	C3—Fe—C8—C7	−108.9 (3)
C6—Fe—C2—C1	−33.7 (13)	C9—Fe—C8—C7	118.4 (4)
C10—Fe—C2—C1	−69.8 (4)	C1—Fe—C8—C7	172.8 (4)
C4—Fe—C2—C1	80.5 (4)	C5—Fe—C8—C7	−42.1 (10)
C1—C2—C3—C4	1.1 (6)	C6—Fe—C8—C7	37.8 (3)
Fe—C2—C3—C4	61.5 (4)	C10—Fe—C8—C7	81.1 (3)
C1—C2—C3—Fe	−60.4 (4)	C4—Fe—C8—C7	−70.0 (4)
C2—Fe—C3—C4	−118.0 (5)	C2—Fe—C8—C11	−31.5 (4)
C8—Fe—C3—C4	131.4 (3)	C3—Fe—C8—C11	11.9 (4)
C7—Fe—C3—C4	87.2 (4)	C7—Fe—C8—C11	120.8 (4)
C9—Fe—C3—C4	171.4 (3)	C9—Fe—C8—C11	−120.8 (4)
C1—Fe—C3—C4	−79.7 (4)	C1—Fe—C8—C11	−66.4 (6)
C5—Fe—C3—C4	−36.4 (3)	C5—Fe—C8—C11	78.7 (10)
C6—Fe—C3—C4	52.0 (6)	C6—Fe—C8—C11	158.7 (4)
C8—Fe—C3—C2	−110.5 (4)	C10—Fe—C8—C11	−158.1 (4)
C7—Fe—C3—C2	−154.8 (3)	C4—Fe—C8—C11	50.8 (4)
C9—Fe—C3—C2	−70.6 (4)	C7—C8—C9—C10	0.1 (5)
C1—Fe—C3—C2	38.3 (3)	C11—C8—C9—C10	174.5 (4)
C5—Fe—C3—C2	81.6 (4)	Fe—C8—C9—C10	59.8 (3)
C6—Fe—C3—C2	170.0 (4)	C7—C8—C9—Fe	−59.7 (3)
C4—Fe—C3—C2	118.0 (5)	C11—C8—C9—Fe	114.7 (4)
C2—C3—C4—C5	−1.6 (6)	C2—Fe—C9—C10	131.2 (4)
Fe—C3—C4—C5	58.7 (4)	C8—Fe—C9—C10	−119.7 (4)
C2—C3—C4—Fe	−60.3 (4)	C7—Fe—C9—C10	−81.0 (3)
C2—Fe—C4—C5	−81.7 (4)	C1—Fe—C9—C10	87.2 (4)
C3—Fe—C4—C5	−120.4 (5)	C5—Fe—C9—C10	52.1 (5)
C8—Fe—C4—C5	171.0 (3)	C6—Fe—C9—C10	−37.2 (3)
C7—Fe—C4—C5	130.2 (3)	C4—Fe—C9—C10	−156.6 (10)
C9—Fe—C4—C5	−158.0 (10)	C2—Fe—C9—C8	−109.1 (3)
C1—Fe—C4—C5	−37.2 (3)	C3—Fe—C9—C8	−68.2 (4)
C6—Fe—C4—C5	87.0 (4)	C7—Fe—C9—C8	38.6 (3)
C10—Fe—C4—C5	52.1 (6)	C1—Fe—C9—C8	−153.1 (3)
C2—Fe—C4—C3	38.7 (4)	C5—Fe—C9—C8	171.8 (4)
C8—Fe—C4—C3	−68.6 (4)	C6—Fe—C9—C8	82.5 (3)
C7—Fe—C4—C3	−109.5 (4)	C10—Fe—C9—C8	119.7 (4)
C9—Fe—C4—C3	−37.6 (12)	C4—Fe—C9—C8	−36.9 (12)
C1—Fe—C4—C3	83.1 (4)	C7—C6—C10—C9	−0.3 (5)
C5—Fe—C4—C3	120.4 (5)	Fe—C6—C10—C9	−58.5 (3)
C6—Fe—C4—C3	−152.7 (4)	C7—C6—C10—Fe	58.2 (3)
C10—Fe—C4—C3	172.5 (4)	C8—C9—C10—C6	0.1 (5)
C3—C4—C5—C1	1.5 (6)	Fe—C9—C10—C6	59.0 (3)
Fe—C4—C5—C1	59.6 (3)	C8—C9—C10—Fe	−58.9 (3)
C3—C4—C5—Fe	−58.1 (4)	C2—Fe—C10—C6	169.9 (3)
C2—C1—C5—C4	−0.8 (6)	C8—Fe—C10—C6	−82.0 (3)
Fe—C1—C5—C4	−60.2 (4)	C7—Fe—C10—C6	−37.2 (3)
C2—C1—C5—Fe	59.3 (4)	C9—Fe—C10—C6	−119.6 (4)
C2—Fe—C5—C4	81.2 (4)	C1—Fe—C10—C6	129.3 (3)
C3—Fe—C5—C4	36.8 (4)	C5—Fe—C10—C6	86.6 (4)
C8—Fe—C5—C4	−34.3 (11)	C4—Fe—C10—C6	52.2 (5)
C7—Fe—C5—C4	−69.1 (4)	C2—Fe—C10—C9	−70.5 (4)
C9—Fe—C5—C4	172.0 (4)	C8—Fe—C10—C9	37.6 (3)
C1—Fe—C5—C4	119.8 (5)	C7—Fe—C10—C9	82.4 (3)
C6—Fe—C5—C4	−109.9 (4)	C1—Fe—C10—C9	−111.1 (3)
C10—Fe—C5—C4	−152.7 (3)	C5—Fe—C10—C9	−153.8 (3)
C2—Fe—C5—C1	−38.6 (4)	C6—Fe—C10—C9	119.6 (4)
C3—Fe—C5—C1	−83.0 (4)	C4—Fe—C10—C9	171.8 (4)
C8—Fe—C5—C1	−154.1 (8)	C9—C8—C11—O1	−169.6 (4)
C7—Fe—C5—C1	171.1 (3)	C7—C8—C11—O1	3.8 (6)
C9—Fe—C5—C1	52.2 (6)	Fe—C8—C11—O1	−82.6 (4)
C6—Fe—C5—C1	130.3 (4)	C9—C8—C11—C12	8.3 (6)
C10—Fe—C5—C1	87.5 (4)	C7—C8—C11—C12	−178.4 (4)
C4—Fe—C5—C1	−119.8 (5)	Fe—C8—C11—C12	95.2 (4)
C2—Fe—C6—C10	−43.4 (12)	O1—C11—C12—C13	0.7 (6)
C8—Fe—C6—C10	81.7 (3)	C8—C11—C12—C13	−177.1 (4)
C7—Fe—C6—C10	120.3 (4)	C11—C12—C13—O2	0.4 (6)
C9—Fe—C6—C10	37.5 (3)	C11—C12—C13—C14	179.0 (4)
C1—Fe—C6—C10	−71.5 (4)	C18—N—C14—C15	−0.4 (6)
C5—Fe—C6—C10	−111.0 (3)	C18—N—C14—C13	−179.2 (3)
C4—Fe—C6—C10	−152.8 (3)	O2—C13—C14—N	−178.7 (3)
C2—Fe—C6—C7	−163.7 (10)	C12—C13—C14—N	2.6 (6)
C3—Fe—C6—C7	52.5 (5)	O2—C13—C14—C15	2.5 (5)
C8—Fe—C6—C7	−38.6 (3)	C12—C13—C14—C15	−176.2 (4)
C9—Fe—C6—C7	−82.7 (3)	N—C14—C15—C16	−0.1 (6)
C1—Fe—C6—C7	168.2 (3)	C13—C14—C15—C16	178.6 (4)
C5—Fe—C6—C7	128.8 (3)	C14—C15—C16—C17	−0.5 (7)
C10—Fe—C6—C7	−120.3 (4)	C15—C16—C17—C18	1.6 (7)
C4—Fe—C6—C7	86.9 (3)	C14—N—C18—C17	1.6 (6)
C10—C6—C7—C8	0.4 (5)	C16—C17—C18—N	−2.3 (7)
Fe—C6—C7—C8	59.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···O1	0.82	1.76	2.495 (5)	148
C4—H4···O2ⁱ	0.98	2.57	3.351 (6)	137

Symmetry code: (i) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[Fe(C₅H₅)(C₁₃H₁₀NO₂)]
M_r	333.16
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	10.547 (2), 12.804 (3), 11.195 (2)
β (°)	104.08 (3)
V (Å³)	1466.4 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.03
Crystal size (mm)	0.4 × 0.2 × 0.1

Data collection
Diffractometer	Enraf–Nonius CAD4 diffractometer
Absorption correction	Empirical (using intensity measurements) via ψ scan (North et al., 1968)
T_min, T_max	0.773, 0.901
No. of measured, independent and observed [I > 2σ(I)] reflections	2721, 2577, 1949
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.130, 1.10
No. of reflections	2577
No. of parameters	200
No. of restraints	6
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.44, −0.32

Computer programs: CAD-4 Software(Enraf–Nonius,1989), CAD-4 Software, XCAD4 (Harms & Wocadlo,1995), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), PLATON.

Selected geometric parameters (Å, º) top

O1—C11	1.293 (5)	C11—C12	1.415 (5)
O2—C13	1.303 (5)	C12—C13	1.361 (6)
C8—C11	1.450 (6)	C13—C14	1.484 (6)

O1—C11—C8	118.3 (4)	O2—C13—C12	122.4 (4)
O1—C11—C12	119.5 (4)	O2—C13—C14	114.5 (4)
C8—C11—C12	122.2 (4)	C12—C13—C14	123.2 (4)
C11—C12—C13	121.4 (4)