2-Ferrocenyl-6-(3-nitro­phen­yl)quinoline

Yuan, X.-E.; Shi, G.-Q.; Geng, X.; Hao, X.-Q.; Song, M.-P.

doi:10.1107/S1600536814004899

metal-organic compounds

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ISSN: 2056-9890

Volume 70| Part 4| April 2014| Page m129

doi:10.1107/S1600536814004899

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2-Ferrocenyl-6-(3-nitrophenyl)quinoline

Xiao-Er Yuan,^a Guo-Qing Shi,^a,^b Xin Geng,^a Xin-Qi Hao ^a ^* and Mao-Ping Song ^a

^aCollege of Chemistry and Molecular Engineering, Zhengzhou University, Henan, Zhengzhou 450001, People's Republic of China, and ^bSchool of Food and Bioengineering, Zhengzhou, University of Light Industry, Henan, Zhengzhou 450052, People's Republic of China
^*Correspondence e-mail: xqhao@zzu.edu.cn

(Received 10 February 2014; accepted 3 March 2014; online 8 March 2014)

In the title compound, [Fe(C₅H₅)(C₂₀H₁₃N₂O₂)], the substituted cyclopentadienyl ring and quinoline system are approximately coplanar, making a dihedral angle of 5.18 (6)°, while the dihedral angle between the quinoline system and the benzene ring is 28.45 (8)°. There is high thermal motion in the free cyclopentadienyl ring compared with the substituted cyclopentadienyl ring. The conformation of the two cyclopentadienyl rings in the ferrocenyl moiety is eclipsed.

CCDC reference: 989588

Related literature

For ferrocenyl derivatives, see: Staveren & Metzler-Nolte (2004 ); Stepnicka (2008 ); Xu et al. (2010 ). For quinolines, see: Carey et al. (2006 ); Michael (2007 ). For the synthesis, see: Xu et al. (2013 ).

Experimental

Crystal data

[Fe(C₅H₅)(C₂₀H₁₃N₂O₂)]
M_r = 434.26
Monoclinic, P 2₁ /c
a = 12.0523 (15) Å
b = 6.6997 (8) Å
c = 23.918 (3) Å
β = 91.018 (2)°
V = 1931.0 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.81 mm⁻¹
T = 296 K
0.41 × 0.32 × 0.25 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.733, T_max = 0.824
10490 measured reflections
3478 independent reflections
2591 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.092
S = 1.01
3478 reflections
271 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Data collection: APEX2 (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: SHELXL97.

Supporting information

CCDC reference: 989588

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536814004899/fj2663sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814004899/fj2663Isup2.hkl

checkCIF report

Comment top

In recent years, there has been an increasing interest in the design of new ferrocenyl derivatives, owing to their utility in diverse fields of chemistry, such as organic synthesis, catalysis and materials science (Staveren & Metzler-Nolte 2004; Stepnicka 2008; Xu et al., 2010). In addition, quinolines and their derivatives are important natural products (Carey et al., 2006; Michael 2007). Here we report the crystal structure of the title compound, derived from the via A-alkylation and Suzuki reaction of acetylferrocene, (2-amino-5-bromophenyl)methanol and 3-nitrylphenylboronic acid.

A view on the molecular structure of the title compound is given in Fig. 1. The two cyclopentadienyl rings are almost parallel (dihedral angle of 0.94 (3)°). The substituted cyclopentadienyl and quinolinyl ring are approximately coplanar, making dihedral angle of 5.18 (6)°, and the dihedral angle between the quinolinyl and phenyl ring is 28.45 (8)°.

Related literature top

For ferrocenyl derivatives, see: Staveren & Metzler-Nolte (2004); Stepnicka (2008); Xu et al. (2010). For quinolines, see: Carey et al. (2006); Michael (2007). For the synthesis, see: Xu et al. (2013).

Experimental top

The title compound was prepared as described in literature (Xu et al. 2013) and recrystallized from dichloromethane/petroleum ether solution at room temperature to give the desired crystals suitable for single-crystal X-ray diffraction.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (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: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound with displacement ellipsoids at the 30% probability level.

2-Ferrocenyl-6-(3-nitrophenyl)quinoline top

Crystal data top

[Fe(C₅H₅)(C₂₀H₁₃N₂O₂)]	F(000) = 896
M_r = 434.26	D_x = 1.494 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2663 reflections
a = 12.0523 (15) Å	θ = 2.4–24.2°
b = 6.6997 (8) Å	µ = 0.81 mm⁻¹
c = 23.918 (3) Å	T = 296 K
β = 91.018 (2)°	Block, red
V = 1931.0 (4) Å³	0.41 × 0.32 × 0.25 mm
Z = 4

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3478 independent reflections
Radiation source: fine-focus sealed tube	2591 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
phi and ω scans	θ_max = 25.5°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −14→14
T_min = 0.733, T_max = 0.824	k = −7→7
10490 measured reflections	l = −28→28

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) = 0.092	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0347P)² + 1.1805P] where P = (F_o² + 2F_c²)/3
3478 reflections	(Δ/σ)_max = 0.018
271 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

[Fe(C₅H₅)(C₂₀H₁₃N₂O₂)]	V = 1931.0 (4) Å³
M_r = 434.26	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.0523 (15) Å	µ = 0.81 mm⁻¹
b = 6.6997 (8) Å	T = 296 K
c = 23.918 (3) Å	0.41 × 0.32 × 0.25 mm
β = 91.018 (2)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3478 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	2591 reflections with I > 2σ(I)
T_min = 0.733, T_max = 0.824	R_int = 0.029
10490 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.092	H-atom parameters constrained
S = 1.01	Δρ_max = 0.25 e Å⁻³
3478 reflections	Δρ_min = −0.33 e Å⁻³
271 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
Fe1	0.48569 (3)	0.34296 (6)	0.382218 (16)	0.04797 (15)
N1	1.19484 (19)	0.4758 (4)	0.00580 (10)	0.0552 (6)
N2	0.75102 (16)	0.3060 (3)	0.29398 (9)	0.0424 (5)
O1	1.2363 (2)	0.5509 (4)	−0.03524 (9)	0.0823 (7)
O2	1.2073 (2)	0.3023 (4)	0.01888 (10)	0.0812 (7)
C1	1.1192 (2)	0.8036 (4)	0.02870 (12)	0.0511 (7)
H1	1.1580	0.8580	−0.0009	0.061*
C2	1.07022 (19)	0.5188 (4)	0.08508 (10)	0.0407 (6)
H2	1.0780	0.3831	0.0925	0.049*
C3	1.1253 (2)	0.6038 (4)	0.04103 (10)	0.0417 (6)
C4	0.9954 (2)	0.8381 (4)	0.10550 (11)	0.0496 (7)
H4	0.9501	0.9195	0.1268	0.060*
C5	1.0530 (2)	0.9205 (4)	0.06205 (12)	0.0565 (8)
H5	1.0473	1.0567	0.0550	0.068*
C6	1.00316 (19)	0.6358 (4)	0.11839 (10)	0.0381 (6)
C7	0.91613 (19)	0.6649 (4)	0.21141 (10)	0.0399 (6)
H7	0.9433	0.7946	0.2138	0.048*
C8	0.85097 (19)	0.5899 (4)	0.25508 (10)	0.0371 (6)
C9	0.81385 (18)	0.3900 (4)	0.25303 (10)	0.0374 (6)
C10	0.8399 (2)	0.2741 (4)	0.20579 (11)	0.0429 (6)
H10	0.8158	0.1425	0.2035	0.051*
C11	0.9000 (2)	0.3533 (4)	0.16343 (11)	0.0427 (6)
H11	0.9148	0.2749	0.1324	0.051*
C12	0.94044 (18)	0.5517 (4)	0.16546 (10)	0.0375 (6)
C13	0.8167 (2)	0.7074 (4)	0.30100 (11)	0.0446 (6)
H13	0.8384	0.8404	0.3039	0.053*
C14	0.7524 (2)	0.6244 (4)	0.34049 (11)	0.0462 (7)
H14	0.7281	0.7008	0.3703	0.055*
C15	0.72202 (19)	0.4201 (4)	0.33620 (10)	0.0407 (6)
C17	0.65424 (19)	0.3269 (4)	0.37962 (11)	0.0438 (6)
C18	0.6198 (2)	0.4143 (5)	0.43104 (11)	0.0515 (7)
H18	0.6393	0.5482	0.4445	0.062*
C19	0.5526 (2)	0.2750 (5)	0.45884 (12)	0.0619 (8)
H19	0.5170	0.2955	0.4949	0.074*
C20	0.5448 (3)	0.1018 (5)	0.42547 (13)	0.0670 (9)
H20	0.5026	−0.0188	0.4344	0.080*
C21	0.6071 (2)	0.1327 (4)	0.37660 (12)	0.0559 (8)
H21	0.6158	0.0373	0.3459	0.067*
C22	0.3303 (4)	0.4402 (15)	0.3922 (2)	0.126 (2)
H22	0.2929	0.4505	0.4281	0.151*
C23	0.3859 (5)	0.3224 (11)	0.3142 (2)	0.1147 (18)
H23	0.3954	0.2306	0.2827	0.138*
C24	0.3271 (3)	0.2868 (10)	0.3600 (3)	0.1131 (18)
H24	0.2872	0.1627	0.3677	0.136*
C25	0.4280 (3)	0.5081 (14)	0.3183 (3)	0.135 (3)
H25	0.4724	0.5773	0.2904	0.162*
C26	0.3912 (6)	0.5869 (8)	0.3687 (4)	0.147 (3)
H26	0.4040	0.7218	0.3833	0.176*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe1	0.0360 (2)	0.0635 (3)	0.0444 (2)	−0.00707 (19)	0.00264 (16)	0.0053 (2)
N1	0.0543 (14)	0.0625 (18)	0.0490 (14)	0.0005 (13)	0.0113 (11)	0.0034 (13)
N2	0.0354 (11)	0.0452 (13)	0.0466 (13)	−0.0026 (10)	0.0048 (10)	−0.0012 (10)
O1	0.1055 (18)	0.0832 (17)	0.0598 (14)	0.0021 (14)	0.0434 (13)	0.0112 (13)
O2	0.1048 (18)	0.0609 (16)	0.0795 (16)	0.0234 (13)	0.0436 (14)	0.0120 (13)
C1	0.0530 (16)	0.0513 (19)	0.0490 (16)	−0.0093 (14)	0.0012 (13)	0.0103 (14)
C2	0.0420 (14)	0.0371 (15)	0.0431 (14)	0.0007 (11)	−0.0010 (11)	0.0036 (12)
C3	0.0395 (14)	0.0480 (17)	0.0376 (14)	−0.0018 (12)	0.0005 (11)	0.0010 (12)
C4	0.0537 (16)	0.0427 (17)	0.0525 (17)	0.0030 (13)	0.0029 (13)	0.0015 (14)
C5	0.0687 (19)	0.0399 (17)	0.0608 (18)	−0.0014 (14)	0.0010 (15)	0.0088 (14)
C6	0.0359 (13)	0.0386 (15)	0.0397 (13)	−0.0016 (11)	−0.0027 (10)	0.0012 (12)
C7	0.0354 (13)	0.0360 (15)	0.0483 (15)	−0.0029 (11)	0.0000 (11)	−0.0017 (12)
C8	0.0301 (12)	0.0392 (15)	0.0419 (14)	−0.0019 (10)	−0.0017 (10)	−0.0040 (11)
C9	0.0292 (12)	0.0414 (16)	0.0414 (14)	−0.0010 (10)	0.0002 (10)	−0.0017 (11)
C10	0.0439 (14)	0.0329 (15)	0.0520 (16)	−0.0011 (11)	0.0048 (12)	−0.0036 (12)
C11	0.0450 (14)	0.0390 (16)	0.0441 (14)	0.0012 (12)	0.0065 (12)	−0.0069 (12)
C12	0.0314 (12)	0.0400 (15)	0.0411 (14)	0.0027 (11)	−0.0008 (10)	0.0004 (12)
C13	0.0458 (15)	0.0413 (16)	0.0466 (15)	−0.0040 (12)	−0.0003 (12)	−0.0062 (12)
C14	0.0456 (15)	0.0512 (18)	0.0419 (15)	−0.0011 (13)	0.0043 (12)	−0.0073 (13)
C15	0.0305 (12)	0.0496 (17)	0.0421 (14)	0.0006 (11)	0.0007 (11)	0.0001 (12)
C17	0.0336 (13)	0.0534 (18)	0.0444 (15)	0.0022 (12)	−0.0002 (11)	0.0034 (13)
C18	0.0418 (15)	0.070 (2)	0.0424 (15)	−0.0027 (14)	0.0003 (12)	0.0001 (14)
C19	0.0558 (18)	0.084 (2)	0.0461 (17)	−0.0022 (17)	0.0056 (14)	0.0113 (17)
C20	0.072 (2)	0.065 (2)	0.064 (2)	−0.0063 (17)	0.0115 (17)	0.0228 (17)
C21	0.0610 (18)	0.0496 (19)	0.0574 (18)	−0.0014 (14)	0.0090 (14)	0.0073 (14)
C22	0.065 (3)	0.235 (8)	0.078 (3)	0.065 (4)	−0.002 (2)	−0.016 (4)
C23	0.090 (3)	0.187 (6)	0.066 (3)	0.032 (4)	−0.030 (3)	−0.032 (3)
C24	0.052 (2)	0.148 (5)	0.139 (5)	−0.037 (3)	−0.030 (3)	0.041 (4)
C25	0.047 (2)	0.217 (7)	0.140 (5)	−0.007 (4)	−0.012 (3)	0.126 (5)
C26	0.122 (5)	0.073 (3)	0.241 (9)	0.029 (3)	−0.112 (6)	−0.017 (4)

Geometric parameters (Å, º) top

Fe1—C22	2.001 (4)	C8—C13	1.419 (3)
Fe1—C25	2.001 (4)	C9—C10	1.411 (3)
Fe1—C24	2.010 (4)	C10—C11	1.364 (3)
Fe1—C23	2.011 (4)	C10—H10	0.9300
Fe1—C26	2.015 (5)	C11—C12	1.416 (3)
Fe1—C18	2.035 (3)	C11—H11	0.9300
Fe1—C21	2.037 (3)	C13—C14	1.353 (3)
Fe1—C17	2.036 (2)	C13—H13	0.9300
Fe1—C20	2.040 (3)	C14—C15	1.420 (4)
Fe1—C19	2.041 (3)	C14—H14	0.9300
N1—O2	1.213 (3)	C15—C17	1.472 (3)
N1—O1	1.218 (3)	C17—C21	1.421 (4)
N1—C3	1.474 (3)	C17—C18	1.430 (4)
N2—C15	1.319 (3)	C18—C19	1.410 (4)
N2—C9	1.370 (3)	C18—H18	0.9800
C1—C3	1.372 (4)	C19—C20	1.411 (5)
C1—C5	1.382 (4)	C19—H19	0.9800
C1—H1	0.9300	C20—C21	1.416 (4)
C2—C3	1.378 (3)	C20—H20	0.9800
C2—C6	1.388 (3)	C21—H21	0.9800
C2—H2	0.9300	C22—C24	1.284 (7)
C4—C5	1.376 (4)	C22—C26	1.354 (8)
C4—C6	1.393 (3)	C22—H22	0.9800
C4—H4	0.9300	C23—C24	1.337 (7)
C5—H5	0.9300	C23—C25	1.347 (8)
C6—C12	1.479 (3)	C23—H23	0.9800
C7—C12	1.372 (3)	C24—H24	0.9800
C7—C8	1.410 (3)	C25—C26	1.396 (8)
C7—H7	0.9300	C25—H25	0.9800
C8—C9	1.413 (3)	C26—H26	0.9800

C22—Fe1—C25	66.3 (2)	C11—C10—H10	119.7
C22—Fe1—C24	37.3 (2)	C9—C10—H10	119.7
C25—Fe1—C24	65.5 (2)	C10—C11—C12	121.8 (2)
C22—Fe1—C23	64.61 (19)	C10—C11—H11	119.1
C25—Fe1—C23	39.2 (2)	C12—C11—H11	119.1
C24—Fe1—C23	38.8 (2)	C7—C12—C11	117.9 (2)
C22—Fe1—C26	39.4 (2)	C7—C12—C6	121.2 (2)
C25—Fe1—C26	40.7 (2)	C11—C12—C6	120.8 (2)
C24—Fe1—C26	65.0 (2)	C14—C13—C8	119.4 (2)
C23—Fe1—C26	66.3 (2)	C14—C13—H13	120.3
C22—Fe1—C18	126.2 (2)	C8—C13—H13	120.3
C25—Fe1—C18	124.8 (2)	C13—C14—C15	119.8 (2)
C24—Fe1—C18	159.7 (2)	C13—C14—H14	120.1
C23—Fe1—C18	159.8 (2)	C15—C14—H14	120.1
C26—Fe1—C18	110.03 (17)	N2—C15—C14	122.9 (2)
C22—Fe1—C21	155.2 (3)	N2—C15—C17	116.9 (2)
C25—Fe1—C21	124.9 (3)	C14—C15—C17	120.2 (2)
C24—Fe1—C21	122.3 (2)	C21—C17—C18	107.3 (2)
C23—Fe1—C21	108.60 (17)	C21—C17—C15	125.4 (2)
C26—Fe1—C21	162.7 (3)	C18—C17—C15	127.3 (3)
C18—Fe1—C21	68.65 (12)	C21—C17—Fe1	69.60 (15)
C22—Fe1—C17	163.1 (3)	C18—C17—Fe1	69.37 (14)
C25—Fe1—C17	109.82 (14)	C15—C17—Fe1	124.45 (18)
C24—Fe1—C17	157.9 (2)	C19—C18—C17	108.2 (3)
C23—Fe1—C17	123.65 (18)	C19—C18—Fe1	69.99 (17)
C26—Fe1—C17	126.8 (3)	C17—C18—Fe1	69.50 (15)
C18—Fe1—C17	41.13 (10)	C19—C18—H18	125.9
C21—Fe1—C17	40.84 (11)	C17—C18—H18	125.9
C22—Fe1—C20	121.1 (3)	Fe1—C18—H18	125.9
C25—Fe1—C20	159.8 (3)	C20—C19—C18	108.1 (3)
C24—Fe1—C20	107.92 (18)	C20—C19—Fe1	69.75 (18)
C23—Fe1—C20	123.7 (2)	C18—C19—Fe1	69.53 (16)
C26—Fe1—C20	156.2 (3)	C20—C19—H19	125.9
C18—Fe1—C20	68.18 (13)	C18—C19—H19	125.9
C21—Fe1—C20	40.64 (11)	Fe1—C19—H19	125.9
C17—Fe1—C20	68.55 (12)	C19—C20—C21	108.4 (3)
C22—Fe1—C19	108.77 (16)	C19—C20—Fe1	69.79 (18)
C25—Fe1—C19	159.3 (3)	C21—C20—Fe1	69.56 (17)
C24—Fe1—C19	123.70 (19)	C19—C20—H20	125.8
C23—Fe1—C19	158.9 (3)	C21—C20—H20	125.8
C26—Fe1—C19	122.6 (3)	Fe1—C20—H20	125.8
C18—Fe1—C19	40.48 (11)	C20—C21—C17	108.0 (3)
C21—Fe1—C19	68.41 (13)	C20—C21—Fe1	69.81 (18)
C17—Fe1—C19	68.71 (11)	C17—C21—Fe1	69.56 (15)
C20—Fe1—C19	40.45 (13)	C20—C21—H21	126.0
O2—N1—O1	123.6 (3)	C17—C21—H21	126.0
O2—N1—C3	118.6 (2)	Fe1—C21—H21	126.0
O1—N1—C3	117.8 (3)	C24—C22—C26	110.1 (5)
C15—N2—C9	117.8 (2)	C24—C22—Fe1	71.7 (3)
C3—C1—C5	117.3 (3)	C26—C22—Fe1	70.9 (3)
C3—C1—H1	121.4	C24—C22—H22	125.0
C5—C1—H1	121.4	C26—C22—H22	124.9
C3—C2—C6	119.9 (2)	Fe1—C22—H22	125.0
C3—C2—H2	120.0	C24—C23—C25	108.0 (5)
C6—C2—H2	120.0	C24—C23—Fe1	70.5 (2)
C1—C3—C2	122.9 (2)	C25—C23—Fe1	70.0 (3)
C1—C3—N1	118.3 (2)	C24—C23—H23	126.0
C2—C3—N1	118.9 (2)	C25—C23—H23	126.0
C5—C4—C6	121.6 (3)	Fe1—C23—H23	126.0
C5—C4—H4	119.2	C22—C24—C23	109.8 (5)
C6—C4—H4	119.2	C22—C24—Fe1	70.9 (3)
C4—C5—C1	120.9 (3)	C23—C24—Fe1	70.6 (2)
C4—C5—H5	119.6	C22—C24—H24	125.1
C1—C5—H5	119.6	C23—C24—H24	125.1
C2—C6—C4	117.4 (2)	Fe1—C24—H24	125.1
C2—C6—C12	122.2 (2)	C23—C25—C26	106.8 (5)
C4—C6—C12	120.4 (2)	C23—C25—Fe1	70.8 (3)
C12—C7—C8	121.7 (2)	C26—C25—Fe1	70.2 (3)
C12—C7—H7	119.1	C23—C25—H25	126.6
C8—C7—H7	119.1	C26—C25—H25	126.6
C7—C8—C9	119.5 (2)	Fe1—C25—H25	126.6
C7—C8—C13	123.3 (2)	C22—C26—C25	105.4 (5)
C9—C8—C13	117.2 (2)	C22—C26—Fe1	69.7 (3)
N2—C9—C10	118.7 (2)	C25—C26—Fe1	69.1 (3)
N2—C9—C8	122.9 (2)	C22—C26—H26	127.3
C10—C9—C8	118.4 (2)	C25—C26—H26	127.3
C11—C10—C9	120.6 (2)	Fe1—C26—H26	127.3

C5—C1—C3—C2	−1.0 (4)	C23—Fe1—C20—C21	79.2 (3)
C5—C1—C3—N1	179.6 (2)	C26—Fe1—C20—C21	−172.6 (4)
C6—C2—C3—C1	1.4 (4)	C18—Fe1—C20—C21	−82.20 (19)
C6—C2—C3—N1	−179.2 (2)	C17—Fe1—C20—C21	−37.79 (18)
O2—N1—C3—C1	174.6 (3)	C19—Fe1—C20—C21	−119.7 (3)
O1—N1—C3—C1	−5.8 (4)	C19—C20—C21—C17	0.1 (4)
O2—N1—C3—C2	−4.8 (4)	Fe1—C20—C21—C17	59.3 (2)
O1—N1—C3—C2	174.8 (2)	C19—C20—C21—Fe1	−59.2 (2)
C6—C4—C5—C1	1.4 (4)	C18—C17—C21—C20	0.0 (3)
C3—C1—C5—C4	−0.4 (4)	C15—C17—C21—C20	−177.8 (2)
C3—C2—C6—C4	−0.4 (4)	Fe1—C17—C21—C20	−59.4 (2)
C3—C2—C6—C12	178.8 (2)	C18—C17—C21—Fe1	59.39 (18)
C5—C4—C6—C2	−1.0 (4)	C15—C17—C21—Fe1	−118.4 (2)
C5—C4—C6—C12	179.8 (2)	C22—Fe1—C21—C20	−50.9 (5)
C12—C7—C8—C9	3.1 (4)	C25—Fe1—C21—C20	−160.8 (3)
C12—C7—C8—C13	−174.8 (2)	C24—Fe1—C21—C20	−79.8 (3)
C15—N2—C9—C10	−176.1 (2)	C23—Fe1—C21—C20	−120.4 (3)
C15—N2—C9—C8	1.9 (3)	C26—Fe1—C21—C20	169.9 (6)
C7—C8—C9—N2	179.5 (2)	C18—Fe1—C21—C20	81.0 (2)
C13—C8—C9—N2	−2.5 (4)	C17—Fe1—C21—C20	119.3 (3)
C7—C8—C9—C10	−2.5 (3)	C19—Fe1—C21—C20	37.30 (19)
C13—C8—C9—C10	175.4 (2)	C22—Fe1—C21—C17	−170.2 (4)
N2—C9—C10—C11	178.5 (2)	C25—Fe1—C21—C17	79.9 (3)
C8—C9—C10—C11	0.4 (4)	C24—Fe1—C21—C17	160.9 (2)
C9—C10—C11—C12	1.3 (4)	C23—Fe1—C21—C17	120.3 (3)
C8—C7—C12—C11	−1.4 (4)	C26—Fe1—C21—C17	50.6 (6)
C8—C7—C12—C6	176.3 (2)	C18—Fe1—C21—C17	−38.33 (16)
C10—C11—C12—C7	−0.8 (4)	C20—Fe1—C21—C17	−119.3 (3)
C10—C11—C12—C6	−178.5 (2)	C19—Fe1—C21—C17	−81.99 (18)
C2—C6—C12—C7	150.7 (2)	C25—Fe1—C22—C24	80.2 (4)
C4—C6—C12—C7	−30.1 (4)	C23—Fe1—C22—C24	36.9 (4)
C2—C6—C12—C11	−31.7 (3)	C26—Fe1—C22—C24	119.8 (5)
C4—C6—C12—C11	147.5 (3)	C18—Fe1—C22—C24	−163.1 (3)
C7—C8—C13—C14	178.7 (2)	C21—Fe1—C22—C24	−42.4 (6)
C9—C8—C13—C14	0.8 (4)	C17—Fe1—C22—C24	160.2 (4)
C8—C13—C14—C15	1.4 (4)	C20—Fe1—C22—C24	−78.6 (4)
C9—N2—C15—C14	0.5 (4)	C19—Fe1—C22—C24	−121.4 (4)
C9—N2—C15—C17	179.8 (2)	C25—Fe1—C22—C26	−39.6 (4)
C13—C14—C15—N2	−2.1 (4)	C24—Fe1—C22—C26	−119.8 (5)
C13—C14—C15—C17	178.5 (2)	C23—Fe1—C22—C26	−82.9 (4)
N2—C15—C17—C21	−7.7 (4)	C18—Fe1—C22—C26	77.1 (5)
C14—C15—C17—C21	171.6 (3)	C21—Fe1—C22—C26	−162.2 (4)
N2—C15—C17—C18	174.9 (2)	C17—Fe1—C22—C26	40.4 (8)
C14—C15—C17—C18	−5.8 (4)	C20—Fe1—C22—C26	161.6 (4)
N2—C15—C17—Fe1	−96.0 (3)	C19—Fe1—C22—C26	118.8 (4)
C14—C15—C17—Fe1	83.4 (3)	C22—Fe1—C23—C24	−35.5 (4)
C22—Fe1—C17—C21	165.7 (6)	C25—Fe1—C23—C24	−118.5 (5)
C25—Fe1—C17—C21	−120.9 (4)	C26—Fe1—C23—C24	−79.0 (4)
C24—Fe1—C17—C21	−47.3 (5)	C18—Fe1—C23—C24	−162.7 (5)
C23—Fe1—C17—C21	−79.4 (3)	C21—Fe1—C23—C24	118.7 (4)
C26—Fe1—C17—C21	−163.4 (4)	C17—Fe1—C23—C24	161.4 (4)
C18—Fe1—C17—C21	118.6 (2)	C20—Fe1—C23—C24	76.2 (4)
C20—Fe1—C17—C21	37.61 (18)	C19—Fe1—C23—C24	40.6 (7)
C19—Fe1—C17—C21	81.20 (19)	C22—Fe1—C23—C25	82.9 (4)
C22—Fe1—C17—C18	47.2 (6)	C24—Fe1—C23—C25	118.5 (5)
C25—Fe1—C17—C18	120.6 (4)	C26—Fe1—C23—C25	39.5 (3)
C24—Fe1—C17—C18	−165.9 (4)	C18—Fe1—C23—C25	−44.2 (7)
C23—Fe1—C17—C18	162.0 (3)	C21—Fe1—C23—C25	−122.8 (4)
C26—Fe1—C17—C18	78.1 (4)	C17—Fe1—C23—C25	−80.1 (4)
C21—Fe1—C17—C18	−118.6 (2)	C20—Fe1—C23—C25	−165.3 (4)
C20—Fe1—C17—C18	−80.96 (19)	C19—Fe1—C23—C25	159.1 (5)
C19—Fe1—C17—C18	−37.37 (18)	C26—C22—C24—C23	0.6 (6)
C22—Fe1—C17—C15	−74.7 (6)	Fe1—C22—C24—C23	−60.2 (3)
C25—Fe1—C17—C15	−1.3 (4)	C26—C22—C24—Fe1	60.8 (4)
C24—Fe1—C17—C15	72.3 (5)	C25—C23—C24—C22	0.1 (6)
C23—Fe1—C17—C15	40.2 (4)	Fe1—C23—C24—C22	60.4 (4)
C26—Fe1—C17—C15	−43.7 (4)	C25—C23—C24—Fe1	−60.2 (3)
C18—Fe1—C17—C15	−121.8 (3)	C25—Fe1—C24—C22	−82.4 (4)
C21—Fe1—C17—C15	119.6 (3)	C23—Fe1—C24—C22	−120.0 (5)
C20—Fe1—C17—C15	157.2 (3)	C26—Fe1—C24—C22	−37.4 (4)
C19—Fe1—C17—C15	−159.2 (3)	C18—Fe1—C24—C22	42.7 (7)
C21—C17—C18—C19	0.0 (3)	C21—Fe1—C24—C22	160.5 (4)
C15—C17—C18—C19	177.7 (2)	C17—Fe1—C24—C22	−164.9 (4)
Fe1—C17—C18—C19	59.50 (19)	C20—Fe1—C24—C22	118.1 (4)
C21—C17—C18—Fe1	−59.53 (19)	C19—Fe1—C24—C22	76.3 (4)
C15—C17—C18—Fe1	118.2 (3)	C22—Fe1—C24—C23	120.0 (5)
C22—Fe1—C18—C19	75.9 (4)	C25—Fe1—C24—C23	37.6 (4)
C25—Fe1—C18—C19	160.2 (3)	C26—Fe1—C24—C23	82.6 (4)
C24—Fe1—C18—C19	45.2 (6)	C18—Fe1—C24—C23	162.7 (5)
C23—Fe1—C18—C19	−167.3 (5)	C21—Fe1—C24—C23	−79.5 (4)
C26—Fe1—C18—C19	117.1 (4)	C17—Fe1—C24—C23	−44.9 (7)
C21—Fe1—C18—C19	−81.3 (2)	C20—Fe1—C24—C23	−121.8 (4)
C17—Fe1—C18—C19	−119.4 (3)	C19—Fe1—C24—C23	−163.6 (4)
C20—Fe1—C18—C19	−37.49 (19)	C24—C23—C25—C26	−0.8 (5)
C22—Fe1—C18—C17	−164.7 (3)	Fe1—C23—C25—C26	−61.4 (3)
C25—Fe1—C18—C17	−80.4 (4)	C24—C23—C25—Fe1	60.6 (3)
C24—Fe1—C18—C17	164.6 (5)	C22—Fe1—C25—C23	−78.3 (4)
C23—Fe1—C18—C17	−47.9 (6)	C24—Fe1—C25—C23	−37.3 (3)
C26—Fe1—C18—C17	−123.5 (4)	C26—Fe1—C25—C23	−116.7 (5)
C21—Fe1—C18—C17	38.07 (16)	C18—Fe1—C25—C23	162.9 (3)
C20—Fe1—C18—C17	81.92 (18)	C21—Fe1—C25—C23	76.2 (3)
C19—Fe1—C18—C17	119.4 (3)	C17—Fe1—C25—C23	119.3 (3)
C17—C18—C19—C20	0.1 (3)	C20—Fe1—C25—C23	37.8 (6)
Fe1—C18—C19—C20	59.3 (2)	C19—Fe1—C25—C23	−158.6 (4)
C17—C18—C19—Fe1	−59.20 (18)	C22—Fe1—C25—C26	38.4 (3)
C22—Fe1—C19—C20	116.3 (4)	C24—Fe1—C25—C26	79.5 (4)
C25—Fe1—C19—C20	−171.4 (4)	C23—Fe1—C25—C26	116.7 (5)
C24—Fe1—C19—C20	77.8 (3)	C18—Fe1—C25—C26	−80.3 (4)
C23—Fe1—C19—C20	48.4 (5)	C21—Fe1—C25—C26	−167.1 (4)
C26—Fe1—C19—C20	157.6 (4)	C17—Fe1—C25—C26	−123.9 (4)
C18—Fe1—C19—C20	−119.4 (3)	C20—Fe1—C25—C26	154.5 (5)
C21—Fe1—C19—C20	−37.47 (18)	C19—Fe1—C25—C26	−41.9 (6)
C17—Fe1—C19—C20	−81.50 (19)	C24—C22—C26—C25	−1.0 (6)
C22—Fe1—C19—C18	−124.3 (4)	Fe1—C22—C26—C25	60.3 (3)
C25—Fe1—C19—C18	−51.9 (5)	C24—C22—C26—Fe1	−61.3 (4)
C24—Fe1—C19—C18	−162.8 (3)	C23—C25—C26—C22	1.1 (5)
C23—Fe1—C19—C18	167.8 (4)	Fe1—C25—C26—C22	−60.7 (3)
C26—Fe1—C19—C18	−83.0 (4)	C23—C25—C26—Fe1	61.8 (3)
C21—Fe1—C19—C18	81.98 (19)	C25—Fe1—C26—C22	116.4 (5)
C17—Fe1—C19—C18	37.95 (17)	C24—Fe1—C26—C22	35.5 (3)
C20—Fe1—C19—C18	119.4 (3)	C23—Fe1—C26—C22	78.3 (4)
C18—C19—C20—C21	−0.1 (4)	C18—Fe1—C26—C22	−123.2 (4)
Fe1—C19—C20—C21	59.0 (2)	C21—Fe1—C26—C22	154.4 (5)
C18—C19—C20—Fe1	−59.1 (2)	C17—Fe1—C26—C22	−166.4 (3)
C22—Fe1—C20—C19	−82.6 (3)	C20—Fe1—C26—C22	−42.0 (7)
C25—Fe1—C20—C19	171.2 (4)	C19—Fe1—C26—C22	−79.9 (4)
C24—Fe1—C20—C19	−121.3 (3)	C22—Fe1—C26—C25	−116.4 (5)
C23—Fe1—C20—C19	−161.1 (2)	C24—Fe1—C26—C25	−80.9 (4)
C26—Fe1—C20—C19	−52.9 (5)	C23—Fe1—C26—C25	−38.1 (3)
C18—Fe1—C20—C19	37.52 (17)	C18—Fe1—C26—C25	120.4 (4)
C21—Fe1—C20—C19	119.7 (3)	C21—Fe1—C26—C25	38.1 (8)
C17—Fe1—C20—C19	81.92 (19)	C17—Fe1—C26—C25	77.2 (4)
C22—Fe1—C20—C21	157.7 (3)	C20—Fe1—C26—C25	−158.4 (5)
C25—Fe1—C20—C21	51.5 (5)	C19—Fe1—C26—C25	163.7 (4)
C24—Fe1—C20—C21	119.0 (3)

Experimental details

Crystal data
Chemical formula	[Fe(C₅H₅)(C₂₀H₁₃N₂O₂)]
M_r	434.26
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	12.0523 (15), 6.6997 (8), 23.918 (3)
β (°)	91.018 (2)
V (Å³)	1931.0 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.81
Crystal size (mm)	0.41 × 0.32 × 0.25

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.733, 0.824
No. of measured, independent and observed [I > 2σ(I)] reflections	10490, 3478, 2591
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.092, 1.01
No. of reflections	3478
No. of parameters	271
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.33

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

This work was sponsored by the National Natural Science Foundation of China (No. 21102135).

References

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