2-Ferrocenyl-6-methyl­pyridin-3-ol

Wang, Z.-Q.; Xu, C.; Cen, F.-F.; Li, Y.-F.; Ji, B.-M.

doi:10.1107/S1600536808039597

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page m1633

doi:10.1107/S1600536808039597

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2-Ferrocenyl-6-methylpyridin-3-ol

Zhi-Qiang Wang,^a Chen Xu,^a Fei-Fei Cen,^b Ying-Fei Li ^b and Bao-Ming Ji ^a ^*

^aCollege of Chemistry and Chemical Engineering, Luoyang Normal University, Luoyang 471022, People's Republic of China, and ^bChemical Engineering and Pharmaceutics School, Henan University of Science and Technology, Luoyang 471003, People's Republic of China
^*Correspondence e-mail: lyhxxjbm@126.com

(Received 16 November 2008; accepted 24 November 2008; online 29 November 2008)

In the title compound, [Fe(C₅H₅)(C₁₁H₁₀NO)], the dihedral angle between the pyridyl and substituted cyclopentadienyl rings is 20.4 (3)°. The H atoms of the methyl group are disordered over two positions; their site-occupation factors were fixed at 0.5. The crystal structure is stabilized by well defined intermolecular O—H⋯N and C—H⋯O hydrogen bonds, leading to the formation of a two-dimensional network parallel to (101).

Related literature

For ferrocene and its derivatives, see: Beletskaya et al. (2001 ); Hayashi & Togni (1995 ); Kealy & Pauson (1951 ); Sarhan & Izumi (2003 ); Staveren & Metzler-Nolte (2004 ); Xu et al. (2007 ).

Experimental

Crystal data

[Fe(C₅H₅)(C₁₁H₁₀NO)]
M_r = 293.14
Monoclinic, P 2₁ /n
a = 10.4370 (13) Å
b = 12.7196 (15) Å
c = 10.5424 (13) Å
β = 111.0330 (10)°
V = 1306.3 (3) Å³
Z = 4
Mo Kα radiation
μ = 1.14 mm⁻¹
T = 291 (2) K
0.37 × 0.23 × 0.21 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.675, T_max = 0.793
7569 measured reflections
2422 independent reflections
1970 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.099
S = 1.08
2422 reflections
173 parameters
H-atom parameters constrained
Δρ_max = 0.63 e Å⁻³
Δρ_min = −0.54 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1ⁱ	0.82	1.96	2.774 (3)	169
C7—H7⋯O1	0.98	2.39	2.866 (4)	109
Symmetry code: (i) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; 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/S1600536808039597/fj2173sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808039597/fj2173Isup2.hkl

checkCIF report

Comment top

Since the discovery of ferrocene in the 1950's (Kealy & Pauson, 1951), the fascinating structural properties of ferrocene and its derivatives have been the subject of increasing interest in all fields of organometallic chemistry (Hayashi et al., 1995; Staveren et al., 2004; Xu et al., 2007). Among them, ferrocene-heterocycles are one of the most important ones (Sarhan & Izumi, 2003). Herein we report the crystal structure of the title compound.

A view of the molecular structure of the title compound is given in Fig.1. The hydrogen atoms of methyl groups are disordered; site-occupation factors were fixed at 0.5. The pyridyl and Cp ring form a dihedral angle of 20.4 (3)°. In the crystal of the title compound, intermolecular O—H···N and C—H···O hydrogen bonds are present(Table 1), resulting in a two-dimensional supramolecular architecture(Fig.2).

Related literature top

For ferrocene and its derivatives, see: Beletskaya et al. (2001); Hayashi & Togni (1995); Kealy & Pauson (1951); Sarhan & Izumi (2003); Staveren & Metzler-Nolte (2004); Xu et al. (2007).

Experimental top

The title compound was prepared as described in literature (Beletskaya et al., 2001) and recrystallized from dichloromethane-petroleum ether solution at room temperature to give the desired product as red crystals suitable for single-crystal X-ray diffraction.

Computing details top

Data collection: SMART (Bruker, 2004); cell refinement: SMART (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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. The molecular structure of the title compound with displacement ellipsoids at the 30% probability level. Only one disordered component of the methyl group is shown.
	Fig. 2. Partial view of the crystal packing showing the intermolecular O—H···N and C—H···O hydrogen bonds. One disordered component of the methyl group has been omitted for clarity.

2-Ferrocenyl-6-methylpyridin-3-ol top

Crystal data top

[Fe(C₅H₅)(C₁₁H₁₀NO)]	F(000) = 608
M_r = 293.14	D_x = 1.491 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2766 reflections
a = 10.4370 (13) Å	θ = 2.4–25.0°
b = 12.7196 (15) Å	µ = 1.14 mm⁻¹
c = 10.5424 (13) Å	T = 291 K
β = 111.033 (1)°	Block, red
V = 1306.3 (3) Å³	0.37 × 0.23 × 0.21 mm
Z = 4

Data collection top

Bruker SMART APEX CCD diffractometer	2422 independent reflections
Radiation source: fine-focus sealed tube	1970 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
ϕ and ω scans	θ_max = 25.5°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→12
T_min = 0.675, T_max = 0.794	k = −15→15
7569 measured reflections	l = −12→12

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.099	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.046P)² + 0.7167P] where P = (F_o² + 2F_c²)/3
2422 reflections	(Δ/σ)_max = 0.001
173 parameters	Δρ_max = 0.63 e Å⁻³
0 restraints	Δρ_min = −0.54 e Å⁻³

Crystal data top

[Fe(C₅H₅)(C₁₁H₁₀NO)]	V = 1306.3 (3) Å³
M_r = 293.14	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.4370 (13) Å	µ = 1.14 mm⁻¹
b = 12.7196 (15) Å	T = 291 K
c = 10.5424 (13) Å	0.37 × 0.23 × 0.21 mm
β = 111.033 (1)°

Data collection top

Bruker SMART APEX CCD diffractometer	2422 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1970 reflections with I > 2σ(I)
T_min = 0.675, T_max = 0.794	R_int = 0.021
7569 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.099	H-atom parameters constrained
S = 1.09	Δρ_max = 0.63 e Å⁻³
2422 reflections	Δρ_min = −0.54 e Å⁻³
173 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	Occ. (<1)
Fe1	0.35569 (4)	1.02041 (3)	0.20685 (4)	0.04595 (16)
O1	0.5672 (2)	0.78281 (18)	0.36235 (18)	0.0576 (5)
H1	0.6489	0.7688	0.3993	0.086*
N1	0.3444 (2)	0.74252 (16)	0.0124 (2)	0.0424 (5)
C1	0.3813 (5)	1.1764 (3)	0.1792 (5)	0.0962 (14)
H1A	0.3075	1.2283	0.1454	0.115*
C2	0.4350 (5)	1.1151 (3)	0.0982 (4)	0.0905 (13)
H2	0.4057	1.1177	−0.0011	0.109*
C3	0.5377 (4)	1.0523 (3)	0.1836 (4)	0.0788 (11)
H3	0.5932	1.0019	0.1552	0.095*
C4	0.5481 (4)	1.0718 (3)	0.3185 (4)	0.0827 (11)
H4	0.6125	1.0386	0.4004	0.099*
C5	0.4490 (4)	1.1502 (3)	0.3136 (4)	0.0856 (12)
H5	0.4325	1.1806	0.3918	0.103*
C6	0.3115 (3)	0.8626 (2)	0.1744 (3)	0.0452 (6)
C7	0.3146 (3)	0.8949 (3)	0.3049 (3)	0.0573 (7)
H7	0.3754	0.8666	0.3922	0.069*
C8	0.2150 (3)	0.9752 (3)	0.2872 (4)	0.0693 (9)
H8	0.1948	1.0114	0.3600	0.083*
C9	0.1511 (3)	0.9943 (3)	0.1476 (4)	0.0778 (11)
H9	0.0787	1.0462	0.1061	0.093*
C10	0.2095 (3)	0.9257 (3)	0.0766 (3)	0.0638 (9)
H10	0.1849	0.9227	−0.0222	0.077*
C11	0.3946 (2)	0.78116 (19)	0.1409 (2)	0.0389 (6)
C12	0.5209 (3)	0.7445 (2)	0.2335 (2)	0.0419 (6)
C13	0.5943 (3)	0.6722 (2)	0.1894 (3)	0.0487 (7)
H13	0.6780	0.6472	0.2490	0.058*
C14	0.5436 (3)	0.6372 (2)	0.0573 (3)	0.0489 (6)
H14	0.5936	0.5896	0.0264	0.059*
C15	0.4175 (3)	0.6734 (2)	−0.0295 (3)	0.0455 (6)
C16	0.3599 (3)	0.6378 (3)	−0.1758 (3)	0.0637 (8)
H16A	0.2724	0.6705	−0.2207	0.096*	0.50
H16B	0.3490	0.5628	−0.1790	0.096*	0.50
H16C	0.4217	0.6574	−0.2206	0.096*	0.50
H16D	0.4230	0.5900	−0.1929	0.096*	0.50
H16E	0.3464	0.6977	−0.2345	0.096*	0.50
H16F	0.2737	0.6030	−0.1929	0.096*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe1	0.0494 (3)	0.0480 (3)	0.0396 (2)	0.00711 (17)	0.01483 (18)	−0.00218 (16)
O1	0.0420 (11)	0.0758 (14)	0.0404 (10)	0.0147 (10)	−0.0031 (8)	−0.0069 (9)
N1	0.0351 (11)	0.0414 (12)	0.0407 (11)	−0.0034 (9)	0.0014 (9)	0.0023 (9)
C1	0.143 (4)	0.044 (2)	0.120 (4)	0.011 (2)	0.070 (3)	−0.003 (2)
C2	0.150 (4)	0.059 (2)	0.088 (3)	−0.012 (2)	0.074 (3)	−0.002 (2)
C3	0.080 (3)	0.067 (2)	0.110 (3)	−0.024 (2)	0.058 (2)	−0.031 (2)
C4	0.063 (2)	0.089 (3)	0.092 (3)	−0.021 (2)	0.022 (2)	−0.033 (2)
C5	0.102 (3)	0.076 (2)	0.091 (3)	−0.020 (2)	0.050 (2)	−0.039 (2)
C6	0.0298 (13)	0.0498 (16)	0.0499 (15)	−0.0026 (11)	0.0069 (11)	0.0015 (12)
C7	0.0532 (18)	0.068 (2)	0.0575 (17)	0.0024 (15)	0.0282 (14)	0.0088 (14)
C8	0.0517 (19)	0.085 (2)	0.084 (2)	0.0068 (17)	0.0393 (19)	−0.0064 (18)
C9	0.0382 (17)	0.090 (3)	0.089 (3)	0.0194 (17)	0.0033 (18)	−0.013 (2)
C10	0.0414 (16)	0.071 (2)	0.0606 (18)	0.0121 (15)	−0.0037 (14)	−0.0132 (16)
C11	0.0315 (13)	0.0380 (13)	0.0413 (13)	−0.0045 (10)	0.0060 (11)	0.0036 (10)
C12	0.0370 (14)	0.0419 (14)	0.0375 (13)	−0.0012 (11)	0.0019 (11)	0.0020 (10)
C13	0.0405 (15)	0.0439 (15)	0.0489 (15)	0.0084 (12)	0.0003 (12)	0.0034 (12)
C14	0.0488 (16)	0.0385 (14)	0.0525 (15)	0.0045 (12)	0.0097 (13)	−0.0019 (11)
C15	0.0464 (16)	0.0372 (14)	0.0450 (14)	−0.0056 (12)	0.0067 (12)	−0.0005 (11)
C16	0.063 (2)	0.0625 (19)	0.0502 (17)	0.0023 (16)	0.0019 (15)	−0.0102 (14)

Geometric parameters (Å, º) top

Fe1—C8	2.024 (3)	C6—C7	1.426 (4)
Fe1—C9	2.025 (3)	C6—C10	1.433 (4)
Fe1—C7	2.029 (3)	C6—C11	1.473 (4)
Fe1—C2	2.032 (4)	C7—C8	1.421 (4)
Fe1—C4	2.036 (3)	C7—H7	0.9800
Fe1—C1	2.036 (4)	C8—C9	1.401 (5)
Fe1—C5	2.038 (4)	C8—H8	0.9800
Fe1—C10	2.040 (3)	C9—C10	1.421 (5)
Fe1—C3	2.041 (4)	C9—H9	0.9800
Fe1—C6	2.061 (3)	C10—H10	0.9800
O1—C12	1.358 (3)	C11—C12	1.408 (3)
O1—H1	0.8200	C12—C13	1.381 (4)
N1—C15	1.339 (3)	C13—C14	1.374 (4)
N1—C11	1.357 (3)	C13—H13	0.9300
C1—C5	1.377 (6)	C14—C15	1.385 (4)
C1—C2	1.412 (5)	C14—H14	0.9300
C1—H1A	0.9800	C15—C16	1.509 (4)
C2—C3	1.381 (6)	C16—H16A	0.9600
C2—H2	0.9800	C16—H16B	0.9600
C3—C4	1.408 (5)	C16—H16C	0.9600
C3—H3	0.9800	C16—H16D	0.9600
C4—C5	1.425 (6)	C16—H16E	0.9600
C4—H4	0.9800	C16—H16F	0.9600
C5—H5	0.9800

C8—Fe1—C9	40.49 (16)	C1—C5—Fe1	70.2 (2)
C8—Fe1—C7	41.06 (13)	C4—C5—Fe1	69.5 (2)
C9—Fe1—C7	68.66 (15)	C1—C5—H5	126.2
C8—Fe1—C2	155.18 (17)	C4—C5—H5	126.2
C9—Fe1—C2	121.4 (2)	Fe1—C5—H5	126.2
C7—Fe1—C2	163.08 (15)	C7—C6—C10	106.6 (3)
C8—Fe1—C4	124.23 (16)	C7—C6—C11	128.5 (2)
C9—Fe1—C4	160.47 (16)	C10—C6—C11	124.9 (3)
C7—Fe1—C4	107.62 (16)	C7—C6—Fe1	68.41 (17)
C2—Fe1—C4	67.60 (19)	C10—C6—Fe1	68.77 (17)
C8—Fe1—C1	119.26 (17)	C11—C6—Fe1	127.50 (18)
C9—Fe1—C1	107.08 (18)	C8—C7—C6	108.5 (3)
C7—Fe1—C1	154.37 (15)	C8—C7—Fe1	69.29 (19)
C2—Fe1—C1	40.61 (16)	C6—C7—Fe1	70.80 (16)
C4—Fe1—C1	67.5 (2)	C8—C7—H7	125.7
C8—Fe1—C5	105.90 (16)	C6—C7—H7	125.7
C9—Fe1—C5	123.03 (16)	Fe1—C7—H7	125.7
C7—Fe1—C5	120.16 (16)	C9—C8—C7	108.2 (3)
C2—Fe1—C5	67.68 (17)	C9—C8—Fe1	69.8 (2)
C4—Fe1—C5	40.93 (16)	C7—C8—Fe1	69.66 (17)
C1—Fe1—C5	39.52 (16)	C9—C8—H8	125.9
C8—Fe1—C10	68.53 (15)	C7—C8—H8	125.9
C9—Fe1—C10	40.92 (14)	Fe1—C8—H8	125.9
C7—Fe1—C10	68.58 (14)	C8—C9—C10	108.3 (3)
C2—Fe1—C10	109.16 (17)	C8—C9—Fe1	69.71 (19)
C4—Fe1—C10	157.32 (14)	C10—C9—Fe1	70.09 (18)
C1—Fe1—C10	125.72 (18)	C8—C9—H9	125.8
C5—Fe1—C10	160.69 (16)	C10—C9—H9	125.8
C8—Fe1—C3	162.32 (18)	Fe1—C9—H9	125.8
C9—Fe1—C3	156.78 (18)	C9—C10—C6	108.3 (3)
C7—Fe1—C3	126.37 (16)	C9—C10—Fe1	68.99 (19)
C2—Fe1—C3	39.63 (17)	C6—C10—Fe1	70.33 (16)
C4—Fe1—C3	40.41 (15)	C9—C10—H10	125.9
C1—Fe1—C3	67.29 (18)	C6—C10—H10	125.9
C5—Fe1—C3	67.95 (15)	Fe1—C10—H10	125.9
C10—Fe1—C3	122.69 (14)	N1—C11—C12	120.2 (2)
C8—Fe1—C6	68.91 (13)	N1—C11—C6	116.3 (2)
C9—Fe1—C6	68.94 (13)	C12—C11—C6	123.5 (2)
C7—Fe1—C6	40.79 (11)	O1—C12—C13	122.3 (2)
C2—Fe1—C6	126.58 (13)	O1—C12—C11	118.9 (2)
C4—Fe1—C6	121.60 (15)	C13—C12—C11	118.8 (2)
C1—Fe1—C6	163.36 (16)	C14—C13—C12	119.9 (2)
C5—Fe1—C6	156.22 (16)	C14—C13—H13	120.0
C10—Fe1—C6	40.90 (11)	C12—C13—H13	120.0
C3—Fe1—C6	109.62 (13)	C13—C14—C15	119.4 (3)
C12—O1—H1	109.5	C13—C14—H14	120.3
C15—N1—C11	120.4 (2)	C15—C14—H14	120.3
C5—C1—C2	108.7 (4)	N1—C15—C14	121.3 (2)
C5—C1—Fe1	70.3 (2)	N1—C15—C16	118.0 (2)
C2—C1—Fe1	69.5 (2)	C14—C15—C16	120.7 (3)
C5—C1—H1A	125.7	C15—C16—H16A	109.5
C2—C1—H1A	125.7	C15—C16—H16B	109.5
Fe1—C1—H1A	125.7	H16A—C16—H16B	109.5
C3—C2—C1	108.0 (4)	C15—C16—H16C	109.5
C3—C2—Fe1	70.5 (2)	H16A—C16—H16C	109.5
C1—C2—Fe1	69.9 (2)	H16B—C16—H16C	109.5
C3—C2—H2	126.0	C15—C16—H16D	109.5
C1—C2—H2	126.0	H16A—C16—H16D	141.1
Fe1—C2—H2	126.0	H16B—C16—H16D	56.3
C2—C3—C4	108.5 (4)	H16C—C16—H16D	56.3
C2—C3—Fe1	69.8 (2)	C15—C16—H16E	109.5
C4—C3—Fe1	69.6 (2)	H16A—C16—H16E	56.3
C2—C3—H3	125.8	H16B—C16—H16E	141.1
C4—C3—H3	125.8	H16C—C16—H16E	56.3
Fe1—C3—H3	125.8	H16D—C16—H16E	109.5
C3—C4—C5	107.2 (4)	C15—C16—H16F	109.5
C3—C4—Fe1	70.0 (2)	H16A—C16—H16F	56.3
C5—C4—Fe1	69.6 (2)	H16B—C16—H16F	56.3
C3—C4—H4	126.4	H16C—C16—H16F	141.1
C5—C4—H4	126.4	H16D—C16—H16F	109.5
Fe1—C4—H4	126.4	H16E—C16—H16F	109.5
C1—C5—C4	107.7 (3)

C8—Fe1—C1—C5	79.3 (3)	C8—Fe1—C6—C11	−160.5 (3)
C9—Fe1—C1—C5	121.6 (3)	C9—Fe1—C6—C11	155.9 (3)
C7—Fe1—C1—C5	45.4 (5)	C7—Fe1—C6—C11	−122.7 (3)
C2—Fe1—C1—C5	−119.8 (4)	C2—Fe1—C6—C11	41.8 (3)
C4—Fe1—C1—C5	−38.5 (2)	C4—Fe1—C6—C11	−42.4 (3)
C10—Fe1—C1—C5	162.7 (2)	C1—Fe1—C6—C11	76.9 (6)
C3—Fe1—C1—C5	−82.4 (3)	C5—Fe1—C6—C11	−79.0 (4)
C6—Fe1—C1—C5	−165.0 (4)	C10—Fe1—C6—C11	118.3 (3)
C8—Fe1—C1—C2	−160.9 (3)	C3—Fe1—C6—C11	0.7 (3)
C9—Fe1—C1—C2	−118.6 (3)	C10—C6—C7—C8	0.8 (3)
C7—Fe1—C1—C2	165.3 (3)	C11—C6—C7—C8	−179.3 (3)
C4—Fe1—C1—C2	81.3 (3)	Fe1—C6—C7—C8	59.2 (2)
C5—Fe1—C1—C2	119.8 (4)	C10—C6—C7—Fe1	−58.4 (2)
C10—Fe1—C1—C2	−77.4 (3)	C11—C6—C7—Fe1	121.5 (3)
C3—Fe1—C1—C2	37.4 (3)	C9—Fe1—C7—C8	−37.4 (2)
C6—Fe1—C1—C2	−45.2 (7)	C2—Fe1—C7—C8	−167.0 (5)
C5—C1—C2—C3	−0.9 (5)	C4—Fe1—C7—C8	122.3 (2)
Fe1—C1—C2—C3	−60.5 (3)	C1—Fe1—C7—C8	47.7 (5)
C5—C1—C2—Fe1	59.6 (3)	C5—Fe1—C7—C8	79.3 (3)
C8—Fe1—C2—C3	161.4 (3)	C10—Fe1—C7—C8	−81.5 (2)
C9—Fe1—C2—C3	−162.0 (2)	C3—Fe1—C7—C8	163.0 (2)
C7—Fe1—C2—C3	−39.2 (6)	C6—Fe1—C7—C8	−119.5 (3)
C4—Fe1—C2—C3	37.5 (2)	C8—Fe1—C7—C6	119.5 (3)
C1—Fe1—C2—C3	118.6 (4)	C9—Fe1—C7—C6	82.08 (19)
C5—Fe1—C2—C3	81.9 (3)	C2—Fe1—C7—C6	−47.5 (6)
C10—Fe1—C2—C3	−118.5 (2)	C4—Fe1—C7—C6	−118.27 (18)
C6—Fe1—C2—C3	−76.1 (3)	C1—Fe1—C7—C6	167.2 (4)
C8—Fe1—C2—C1	42.8 (5)	C5—Fe1—C7—C6	−161.19 (19)
C9—Fe1—C2—C1	79.4 (3)	C10—Fe1—C7—C6	37.99 (17)
C7—Fe1—C2—C1	−157.8 (5)	C3—Fe1—C7—C6	−77.6 (2)
C4—Fe1—C2—C1	−81.1 (3)	C6—C7—C8—C9	−0.8 (4)
C5—Fe1—C2—C1	−36.6 (3)	Fe1—C7—C8—C9	59.4 (3)
C10—Fe1—C2—C1	123.0 (3)	C6—C7—C8—Fe1	−60.1 (2)
C3—Fe1—C2—C1	−118.6 (4)	C7—Fe1—C8—C9	−119.4 (3)
C6—Fe1—C2—C1	165.4 (3)	C2—Fe1—C8—C9	51.6 (5)
C1—C2—C3—C4	1.0 (5)	C4—Fe1—C8—C9	163.5 (2)
Fe1—C2—C3—C4	−59.1 (3)	C1—Fe1—C8—C9	82.1 (3)
C1—C2—C3—Fe1	60.1 (3)	C5—Fe1—C8—C9	122.6 (2)
C8—Fe1—C3—C2	−153.9 (4)	C10—Fe1—C8—C9	−37.8 (2)
C9—Fe1—C3—C2	42.0 (5)	C3—Fe1—C8—C9	−170.4 (4)
C7—Fe1—C3—C2	166.8 (2)	C6—Fe1—C8—C9	−81.9 (2)
C4—Fe1—C3—C2	−119.8 (3)	C9—Fe1—C8—C7	119.4 (3)
C1—Fe1—C3—C2	−38.3 (2)	C2—Fe1—C8—C7	171.0 (3)
C5—Fe1—C3—C2	−81.2 (3)	C4—Fe1—C8—C7	−77.1 (3)
C10—Fe1—C3—C2	80.6 (3)	C1—Fe1—C8—C7	−158.5 (2)
C6—Fe1—C3—C2	124.2 (2)	C5—Fe1—C8—C7	−117.9 (2)
C8—Fe1—C3—C4	−34.1 (6)	C10—Fe1—C8—C7	81.6 (2)
C9—Fe1—C3—C4	161.8 (4)	C3—Fe1—C8—C7	−51.0 (6)
C7—Fe1—C3—C4	−73.4 (3)	C6—Fe1—C8—C7	37.56 (19)
C2—Fe1—C3—C4	119.8 (3)	C7—C8—C9—C10	0.4 (4)
C1—Fe1—C3—C4	81.5 (3)	Fe1—C8—C9—C10	59.7 (3)
C5—Fe1—C3—C4	38.6 (3)	C7—C8—C9—Fe1	−59.3 (2)
C10—Fe1—C3—C4	−159.6 (2)	C7—Fe1—C9—C8	37.9 (2)
C6—Fe1—C3—C4	−116.1 (2)	C2—Fe1—C9—C8	−157.3 (2)
C2—C3—C4—C5	−0.7 (4)	C4—Fe1—C9—C8	−44.7 (6)
Fe1—C3—C4—C5	−59.9 (3)	C1—Fe1—C9—C8	−115.3 (2)
C2—C3—C4—Fe1	59.2 (3)	C5—Fe1—C9—C8	−75.0 (3)
C8—Fe1—C4—C3	168.1 (2)	C10—Fe1—C9—C8	119.4 (3)
C9—Fe1—C4—C3	−158.4 (5)	C3—Fe1—C9—C8	172.7 (3)
C7—Fe1—C4—C3	125.9 (3)	C6—Fe1—C9—C8	81.8 (2)
C2—Fe1—C4—C3	−36.8 (2)	C8—Fe1—C9—C10	−119.4 (3)
C1—Fe1—C4—C3	−80.9 (3)	C7—Fe1—C9—C10	−81.5 (2)
C5—Fe1—C4—C3	−118.1 (4)	C2—Fe1—C9—C10	83.3 (3)
C10—Fe1—C4—C3	49.4 (5)	C4—Fe1—C9—C10	−164.1 (5)
C6—Fe1—C4—C3	83.4 (3)	C1—Fe1—C9—C10	125.3 (2)
C8—Fe1—C4—C5	−73.8 (3)	C5—Fe1—C9—C10	165.6 (2)
C9—Fe1—C4—C5	−40.3 (6)	C3—Fe1—C9—C10	53.3 (5)
C7—Fe1—C4—C5	−116.0 (3)	C6—Fe1—C9—C10	−37.6 (2)
C2—Fe1—C4—C5	81.3 (3)	C8—C9—C10—C6	0.1 (4)
C1—Fe1—C4—C5	37.2 (2)	Fe1—C9—C10—C6	59.6 (2)
C10—Fe1—C4—C5	167.5 (4)	C8—C9—C10—Fe1	−59.4 (3)
C3—Fe1—C4—C5	118.1 (4)	C7—C6—C10—C9	−0.6 (4)
C6—Fe1—C4—C5	−158.5 (2)	C11—C6—C10—C9	179.6 (3)
C2—C1—C5—C4	0.5 (5)	Fe1—C6—C10—C9	−58.7 (2)
Fe1—C1—C5—C4	59.6 (3)	C7—C6—C10—Fe1	58.1 (2)
C2—C1—C5—Fe1	−59.1 (3)	C11—C6—C10—Fe1	−121.7 (3)
C3—C4—C5—C1	0.2 (5)	C8—Fe1—C10—C9	37.4 (2)
Fe1—C4—C5—C1	−60.0 (3)	C7—Fe1—C10—C9	81.7 (2)
C3—C4—C5—Fe1	60.2 (2)	C2—Fe1—C10—C9	−116.2 (3)
C8—Fe1—C5—C1	−117.0 (3)	C4—Fe1—C10—C9	166.2 (4)
C9—Fe1—C5—C1	−76.2 (3)	C1—Fe1—C10—C9	−73.9 (3)
C7—Fe1—C5—C1	−159.1 (2)	C5—Fe1—C10—C9	−39.1 (6)
C2—Fe1—C5—C1	37.6 (3)	C3—Fe1—C10—C9	−157.9 (3)
C4—Fe1—C5—C1	118.7 (4)	C6—Fe1—C10—C9	119.6 (3)
C10—Fe1—C5—C1	−46.7 (6)	C8—Fe1—C10—C6	−82.2 (2)
C3—Fe1—C5—C1	80.6 (3)	C9—Fe1—C10—C6	−119.6 (3)
C6—Fe1—C5—C1	169.4 (3)	C7—Fe1—C10—C6	−37.89 (17)
C8—Fe1—C5—C4	124.4 (3)	C2—Fe1—C10—C6	124.2 (2)
C9—Fe1—C5—C4	165.1 (2)	C4—Fe1—C10—C6	46.6 (5)
C7—Fe1—C5—C4	82.2 (3)	C1—Fe1—C10—C6	166.5 (2)
C2—Fe1—C5—C4	−81.1 (3)	C5—Fe1—C10—C6	−158.7 (4)
C1—Fe1—C5—C4	−118.7 (4)	C3—Fe1—C10—C6	82.4 (2)
C10—Fe1—C5—C4	−165.4 (4)	C15—N1—C11—C12	−3.4 (4)
C3—Fe1—C5—C4	−38.1 (3)	C15—N1—C11—C6	175.6 (2)
C6—Fe1—C5—C4	50.7 (4)	C7—C6—C11—N1	160.0 (3)
C8—Fe1—C6—C7	−37.80 (19)	C10—C6—C11—N1	−20.3 (4)
C9—Fe1—C6—C7	−81.3 (2)	Fe1—C6—C11—N1	−109.0 (2)
C2—Fe1—C6—C7	164.5 (2)	C7—C6—C11—C12	−21.1 (4)
C4—Fe1—C6—C7	80.3 (2)	C10—C6—C11—C12	158.7 (3)
C1—Fe1—C6—C7	−160.4 (5)	Fe1—C6—C11—C12	70.0 (3)
C5—Fe1—C6—C7	43.7 (4)	N1—C11—C12—O1	−178.5 (2)
C10—Fe1—C6—C7	−118.9 (3)	C6—C11—C12—O1	2.5 (4)
C3—Fe1—C6—C7	123.4 (2)	N1—C11—C12—C13	2.5 (4)
C8—Fe1—C6—C10	81.1 (2)	C6—C11—C12—C13	−176.4 (2)
C9—Fe1—C6—C10	37.6 (2)	O1—C12—C13—C14	−179.0 (3)
C7—Fe1—C6—C10	118.9 (3)	C11—C12—C13—C14	−0.1 (4)
C2—Fe1—C6—C10	−76.6 (3)	C12—C13—C14—C15	−1.4 (4)
C4—Fe1—C6—C10	−160.8 (2)	C11—N1—C15—C14	1.9 (4)
C1—Fe1—C6—C10	−41.5 (6)	C11—N1—C15—C16	−176.7 (2)
C5—Fe1—C6—C10	162.7 (3)	C13—C14—C15—N1	0.5 (4)
C3—Fe1—C6—C10	−117.7 (2)	C13—C14—C15—C16	179.1 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1ⁱ	0.82	1.96	2.774 (3)	169
C7—H7···O1	0.98	2.39	2.866 (4)	109

Symmetry code: (i) x+1/2, −y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formula	[Fe(C₅H₅)(C₁₁H₁₀NO)]
M_r	293.14
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	291
a, b, c (Å)	10.4370 (13), 12.7196 (15), 10.5424 (13)
β (°)	111.033 (1)
V (Å³)	1306.3 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.14
Crystal size (mm)	0.37 × 0.23 × 0.21

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.675, 0.794
No. of measured, independent and observed [I > 2σ(I)] reflections	7569, 2422, 1970
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.099, 1.09
No. of reflections	2422
No. of parameters	173
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.63, −0.54

Computer programs: SMART (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1ⁱ	0.82	1.96	2.774 (3)	169
C7—H7···O1	0.98	2.39	2.866 (4)	109

Symmetry code: (i) x+1/2, −y+3/2, z+1/2.

Acknowledgements

This work was supported by the Doctoral Foundation of Luoyang Normal University.

References

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