N-(Quinolin-8-yl)ferrocene-1-carbox­amide

Li, X.; Du, L.-Z.

doi:10.1107/S1600536811026341

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page m1113

doi:10.1107/S1600536811026341

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N-(Quinolin-8-yl)ferrocene-1-carboxamide

Xia Li ^a ^* and Ling-Zhi Du ^a

^aDepartment of Chemistry and Chemical Engineering, Henan University of Urban Construction, Pingdingshan, Henan 467044, People's Republic of China
^*Correspondence e-mail: lixia@hncj.edu.cn

(Received 29 June 2011; accepted 3 July 2011; online 23 July 2011)

In the title compound, [Fe(C₅H₅)(C₁₅H₁₁N₂O)], the cyclopentadienyl rings are essentially eclipsed, and the dihedral angle between the cyclopentadienyl ring planes is 0.632 (10)°. The Fe atom is slightly closer to the substituted cyclopentadienyl ring, with an Fe–centroid distance of 1.6374 (3) Å [1.6494 (3) Å for the unsubstituted ring]. The amide group is essentially coplanar with the substituted cyclopentadienyl ring, with an N—C(O)—C—C torsion angle of 2.3 (3)°.

Related literature

For background to the chemical, stereochemical and electrochemical properties of ferrocene, see: Togni & Hayashi (1995 ). Ferrocene has been extensively incorporated into larger compounds in order to take advantage of these properties, see: Abd-El-Aziz & Manners (2007 ); Fang et al. (2001 ); Mata et al. (2001 ). For our research on ferrocenyl derivatives and their metal complexes, see: Li et al. (2008 , 2009 ).

Experimental

Crystal data

[Fe(C₅H₅)(C₁₅H₁₁N₂O)]
M_r = 356.20
Orthorhombic, P b c a
a = 10.1680 (17) Å
b = 12.133 (2) Å
c = 26.079 (4) Å
V = 3217.4 (10) Å³
Z = 8
Mo Kα radiation
μ = 0.95 mm⁻¹
T = 296 K
0.46 × 0.37 × 0.25 mm

Data collection

Rigaku Mercury CCD diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2000 ) T_min = 0.668, T_max = 0.795
18658 measured reflections
3940 independent reflections
2996 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.097
S = 1.01
3940 reflections
222 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Data collection: CrystalClear (Rigaku, 2000); cell refinement: CrystalClear; data reduction: CrystalClear; 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 I, global. DOI: 10.1107/S1600536811026341/fj2441sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811026341/fj2441Isup2.hkl

checkCIF report

Comment top

Due to its special chemical, stereochemical and electrochemical properties (Togni et al., 1995), ferrocene has been extensively incorporated into larger compounds in order to take advantage of these properties (Mata et al., 2001; Abd-El-Aziz et al., 2007; Fang et al., 2001). As a continuation of our research related to ferrocenyl derivatives and their metal complexes (Li et al., 2008; Li et al., 2009), herein we report the crystal structure of 8-(Ferrocenoylamino)quinoline.

The molecular structure of the title compound is composed of a ferrocenyl group and a quinolyl group joined by an organic amide spacer. The Fe—C bond distances within the ferrocene group are in the range of 2.0259 (19)–2.048 (2) Å for the substituted cyclopentadienyl (Cp) ring [C1—C5] and 2.026 (2)–2.039 (2) Å for the unsubstituted Cp ring [C6—C10]. The planar cyclopentadienyl rings of the ferrocenyl unit are nearly parallel to each other [the interplanar angle is 0.632 (10) °]. The Cp rings are essentially eclipsed and the Fe-centroid distances are 1.6374 (3) Å (Cg1) and 1.6494 (3) Å (Cg2) with Cg1 and Cg2 are the centroids of the [C1—C5] and [C6—C10] rings. The [Cg1—Fe1—Cg2] angle is 179.324 (17) °. The carbamoyl group is essentially coplanar with the substituted cyclopentadienyl ring with a deviation of 4.9 (2) °. The angle formed by the carbamoyl group and the quinolyl group system is 9.4 (3) °.

Related literature top

For background to the chemical, stereochemical and electrochemical properties of ferrocene, see: Togni & Hayashi (1995). Ferrocene has been extensively incorporated into larger compounds in order to take advantage of these properties, see: Abd-El-Aziz & Manners (2007); Fang et al. (2001); Mata et al. (2001). For our research on ferrocenyl derivatives and their metal complexes, see: Li et al. (2008, 2009).

Experimental top

A solution of Chlorocarbonyl ferrocene (0.248 g, 1 mmol) in CH₂Cl₂ (20 ml) was added dropwise to a vigorously stirred solution of the 8-Aminoquinoline (0.144 g, 1 mmol) in CH₂Cl₂ (20 ml) containing pyridine (0.5 ml). The stirred reaction mixture was maintained at room temperature for 4 h. Removal of the solvent afforded the crude amide and the residue was recrystallized in dichloromethane/ether to give orange crystals 0.325 g. Yield 91.3%.

Computing details top

Data collection: CrystalClear (Rigaku, 2000); cell refinement: CrystalClear (Rigaku, 2000); data reduction: CrystalClear (Rigaku, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXL97 (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound, showing the atomic numbering and 30% probability displacement ellipsoids.

N-(Quinolin-8-yl)ferrocene-1-carboxamide top

Crystal data top

[Fe(C₅H₅)(C₁₅H₁₁N₂O)]	F(000) = 1472
M_r = 356.20	D_x = 1.471 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	θ = 1.6–28.3°
a = 10.1680 (17) Å	µ = 0.95 mm⁻¹
b = 12.133 (2) Å	T = 296 K
c = 26.079 (4) Å	Block, orange
V = 3217.4 (10) Å³	0.46 × 0.37 × 0.25 mm
Z = 8

Data collection top

Rigaku Mercury CCD diffractometer	3940 independent reflections
Radiation source: fine-focus sealed tube	2996 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
ω scan	θ_max = 28.3°, θ_min = 1.6°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2000)	h = −13→13
T_min = 0.668, T_max = 0.795	k = −12→15
18658 measured reflections	l = −34→29

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.097	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.P)² + 1.0596P] where P = (F_o² + 2F_c²)/3
3940 reflections	(Δ/σ)_max = 0.001
222 parameters	Δρ_max = 0.26 e Å⁻³
0 restraints	Δρ_min = −0.37 e Å⁻³

Crystal data top

[Fe(C₅H₅)(C₁₅H₁₁N₂O)]	V = 3217.4 (10) Å³
M_r = 356.20	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 10.1680 (17) Å	µ = 0.95 mm⁻¹
b = 12.133 (2) Å	T = 296 K
c = 26.079 (4) Å	0.46 × 0.37 × 0.25 mm

Data collection top

Rigaku Mercury CCD diffractometer	3940 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2000)	2996 reflections with I > 2σ(I)
T_min = 0.668, T_max = 0.795	R_int = 0.031
18658 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.097	H-atom parameters constrained
S = 1.01	Δρ_max = 0.26 e Å⁻³
3940 reflections	Δρ_min = −0.37 e Å⁻³
222 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	0.08194 (2)	0.61371 (2)	0.324077 (9)	0.03985 (12)
O1	−0.14938 (18)	0.85691 (16)	0.34733 (7)	0.0757 (5)
N1	0.02468 (18)	0.87266 (15)	0.40153 (7)	0.0471 (4)
N2	0.19232 (16)	0.94139 (13)	0.47326 (6)	0.0433 (4)
C1	−0.04130 (18)	0.69359 (18)	0.37255 (7)	0.0432 (4)
C2	−0.1135 (2)	0.6191 (2)	0.34083 (8)	0.0509 (5)
H2	−0.1811	0.6384	0.3186	0.061*
C3	−0.0656 (2)	0.5119 (2)	0.34881 (8)	0.0580 (6)
H3	−0.0959	0.4483	0.3328	0.070*
C4	0.0368 (2)	0.5175 (2)	0.38554 (8)	0.0585 (6)
H4	0.0856	0.4581	0.3977	0.070*
C5	0.0521 (2)	0.62850 (18)	0.40057 (7)	0.0484 (5)
H5	0.1122	0.6549	0.4245	0.058*
C6	0.1656 (3)	0.7278 (2)	0.27759 (10)	0.0756 (8)
H6	0.1460	0.8027	0.2772	0.091*
C7	0.1037 (2)	0.6449 (3)	0.24815 (9)	0.0741 (8)
H7	0.0355	0.6550	0.2249	0.089*
C8	0.1644 (3)	0.5444 (3)	0.26050 (10)	0.0736 (8)
H8	0.1437	0.4758	0.2468	0.088*
C9	0.2604 (3)	0.5657 (3)	0.29680 (10)	0.0767 (8)
H9	0.3153	0.5133	0.3117	0.092*
C10	0.2614 (2)	0.6765 (3)	0.30727 (11)	0.0775 (8)
H10	0.3171	0.7115	0.3304	0.093*
C11	−0.06124 (18)	0.81347 (19)	0.37209 (7)	0.0475 (5)
C12	0.02430 (18)	0.98542 (16)	0.41223 (7)	0.0419 (4)
C13	−0.0553 (2)	1.0624 (2)	0.38937 (8)	0.0525 (5)
H13	−0.1144	1.0406	0.3641	0.063*
C14	−0.0483 (2)	1.1737 (2)	0.40382 (9)	0.0602 (6)
H14	−0.1021	1.2247	0.3875	0.072*
C15	0.0351 (2)	1.20882 (19)	0.44113 (9)	0.0583 (5)
H15	0.0374	1.2829	0.4503	0.070*
C16	0.1185 (2)	1.13215 (16)	0.46605 (7)	0.0437 (4)
C17	0.11420 (17)	1.02001 (15)	0.45129 (6)	0.0381 (4)
C18	0.2047 (2)	1.16091 (17)	0.50584 (8)	0.0506 (5)
H18	0.2107	1.2338	0.5166	0.061*
C19	0.2793 (2)	1.08233 (18)	0.52850 (8)	0.0512 (5)
H19	0.3351	1.1000	0.5555	0.061*
C20	0.2707 (2)	0.97401 (17)	0.51045 (7)	0.0489 (5)
H20	0.3241	0.9213	0.5258	0.059*
H1	0.078 (2)	0.8400 (19)	0.4191 (8)	0.046 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe1	0.03308 (17)	0.0496 (2)	0.03683 (16)	−0.00552 (11)	0.00144 (10)	−0.00378 (11)
O1	0.0693 (11)	0.0826 (12)	0.0752 (11)	0.0229 (10)	−0.0350 (9)	−0.0182 (9)
N1	0.0441 (9)	0.0508 (10)	0.0464 (9)	0.0082 (8)	−0.0110 (7)	−0.0072 (7)
N2	0.0460 (9)	0.0388 (9)	0.0451 (8)	0.0007 (7)	−0.0054 (7)	−0.0007 (7)
C1	0.0344 (9)	0.0619 (13)	0.0334 (8)	−0.0037 (9)	0.0001 (7)	−0.0077 (8)
C2	0.0341 (10)	0.0756 (16)	0.0431 (10)	−0.0137 (10)	0.0019 (8)	−0.0091 (10)
C3	0.0572 (13)	0.0613 (15)	0.0554 (12)	−0.0254 (11)	0.0076 (10)	−0.0071 (11)
C4	0.0674 (14)	0.0551 (13)	0.0530 (12)	−0.0080 (11)	0.0008 (10)	0.0106 (10)
C5	0.0501 (11)	0.0597 (13)	0.0356 (9)	−0.0065 (10)	−0.0038 (8)	0.0002 (9)
C6	0.0774 (18)	0.0681 (17)	0.0813 (17)	−0.0078 (14)	0.0356 (15)	0.0080 (14)
C7	0.0482 (13)	0.133 (3)	0.0411 (11)	−0.0043 (15)	0.0088 (9)	0.0110 (14)
C8	0.0768 (18)	0.0833 (19)	0.0608 (14)	−0.0106 (15)	0.0243 (13)	−0.0214 (13)
C9	0.0494 (14)	0.106 (2)	0.0749 (16)	0.0155 (15)	0.0118 (12)	−0.0030 (16)
C10	0.0445 (13)	0.113 (3)	0.0748 (16)	−0.0260 (15)	0.0118 (12)	−0.0170 (16)
C11	0.0408 (10)	0.0643 (14)	0.0374 (9)	0.0060 (9)	−0.0037 (8)	−0.0098 (9)
C12	0.0406 (10)	0.0467 (11)	0.0385 (9)	0.0054 (8)	0.0056 (7)	−0.0018 (8)
C13	0.0492 (12)	0.0625 (14)	0.0457 (10)	0.0110 (10)	−0.0004 (9)	0.0057 (10)
C14	0.0623 (14)	0.0544 (14)	0.0640 (13)	0.0192 (11)	0.0068 (11)	0.0163 (11)
C15	0.0645 (14)	0.0443 (12)	0.0660 (13)	0.0077 (11)	0.0078 (11)	0.0087 (10)
C16	0.0476 (10)	0.0360 (10)	0.0475 (10)	0.0009 (8)	0.0121 (8)	0.0050 (8)
C17	0.0390 (9)	0.0388 (10)	0.0366 (8)	0.0017 (8)	0.0064 (7)	0.0027 (7)
C18	0.0603 (13)	0.0368 (10)	0.0548 (11)	−0.0077 (9)	0.0087 (10)	−0.0059 (9)
C19	0.0599 (13)	0.0455 (11)	0.0483 (10)	−0.0104 (10)	−0.0063 (9)	−0.0018 (9)
C20	0.0562 (12)	0.0390 (10)	0.0515 (10)	−0.0009 (9)	−0.0102 (9)	0.0011 (8)

Geometric parameters (Å, º) top

Fe1—C10	2.026 (2)	C6—C10	1.391 (4)
Fe1—C5	2.0258 (19)	C6—C7	1.413 (4)
Fe1—C1	2.0268 (19)	C6—H6	0.9300
Fe1—C6	2.028 (2)	C7—C8	1.404 (4)
Fe1—C7	2.028 (2)	C7—H7	0.9300
Fe1—C9	2.034 (2)	C8—C9	1.384 (4)
Fe1—C4	2.036 (2)	C8—H8	0.9300
Fe1—C2	2.036 (2)	C9—C10	1.372 (4)
Fe1—C8	2.039 (2)	C9—H9	0.9300
Fe1—C3	2.048 (2)	C10—H10	0.9300
O1—C11	1.224 (2)	C12—C13	1.372 (3)
N1—C11	1.367 (3)	C12—C17	1.432 (3)
N1—C12	1.396 (3)	C13—C14	1.405 (4)
N1—H1	0.81 (2)	C13—H13	0.9300
N2—C20	1.316 (2)	C14—C15	1.359 (3)
N2—C17	1.367 (2)	C14—H14	0.9300
C1—C2	1.429 (3)	C15—C16	1.417 (3)
C1—C5	1.435 (3)	C15—H15	0.9300
C1—C11	1.469 (3)	C16—C18	1.402 (3)
C2—C3	1.404 (3)	C16—C17	1.415 (3)
C2—H2	0.9300	C18—C19	1.354 (3)
C3—C4	1.417 (3)	C18—H18	0.9300
C3—H3	0.9300	C19—C20	1.399 (3)
C4—C5	1.412 (3)	C19—H19	0.9300
C4—H4	0.9300	C20—H20	0.9300
C5—H5	0.9300

C10—Fe1—C5	108.35 (10)	C5—C4—H4	125.8
C10—Fe1—C1	120.82 (10)	C3—C4—H4	125.8
C5—Fe1—C1	41.47 (8)	Fe1—C4—H4	126.3
C10—Fe1—C6	40.16 (12)	C4—C5—C1	108.12 (18)
C5—Fe1—C6	126.24 (11)	C4—C5—Fe1	70.04 (12)
C1—Fe1—C6	107.81 (10)	C1—C5—Fe1	69.30 (10)
C10—Fe1—C7	67.67 (11)	C4—C5—H5	125.9
C5—Fe1—C7	164.01 (13)	C1—C5—H5	125.9
C1—Fe1—C7	125.97 (11)	Fe1—C5—H5	126.3
C6—Fe1—C7	40.79 (11)	C10—C6—C7	107.2 (3)
C10—Fe1—C9	39.50 (13)	C10—C6—Fe1	69.85 (15)
C5—Fe1—C9	120.23 (10)	C7—C6—Fe1	69.62 (15)
C1—Fe1—C9	155.04 (10)	C10—C6—H6	126.4
C6—Fe1—C9	67.18 (12)	C7—C6—H6	126.4
C7—Fe1—C9	67.32 (11)	Fe1—C6—H6	125.7
C10—Fe1—C4	126.11 (12)	C8—C7—C6	107.4 (2)
C5—Fe1—C4	40.68 (9)	C8—C7—Fe1	70.25 (14)
C1—Fe1—C4	69.13 (10)	C6—C7—Fe1	69.59 (14)
C6—Fe1—C4	163.18 (11)	C8—C7—H7	126.3
C7—Fe1—C4	154.22 (12)	C6—C7—H7	126.3
C9—Fe1—C4	108.19 (11)	Fe1—C7—H7	125.4
C10—Fe1—C2	156.06 (12)	C9—C8—C7	107.7 (3)
C5—Fe1—C2	68.87 (8)	C9—C8—Fe1	69.94 (14)
C1—Fe1—C2	41.18 (8)	C7—C8—Fe1	69.38 (14)
C6—Fe1—C2	121.07 (11)	C9—C8—H8	126.1
C7—Fe1—C2	108.08 (10)	C7—C8—H8	126.1
C9—Fe1—C2	162.73 (11)	Fe1—C8—H8	126.1
C4—Fe1—C2	68.23 (10)	C10—C9—C8	108.9 (3)
C10—Fe1—C8	66.96 (11)	C10—C9—Fe1	69.91 (14)
C5—Fe1—C8	153.99 (11)	C8—C9—Fe1	70.33 (14)
C1—Fe1—C8	163.43 (10)	C10—C9—H9	125.5
C6—Fe1—C8	67.85 (12)	C8—C9—H9	125.5
C7—Fe1—C8	40.38 (12)	Fe1—C9—H9	125.8
C9—Fe1—C8	39.72 (11)	C9—C10—C6	108.8 (2)
C4—Fe1—C8	119.76 (12)	C9—C10—Fe1	70.60 (15)
C2—Fe1—C8	126.08 (10)	C6—C10—Fe1	70.00 (14)
C10—Fe1—C3	162.78 (13)	C9—C10—H10	125.6
C5—Fe1—C3	68.49 (9)	C6—C10—H10	125.6
C1—Fe1—C3	68.83 (9)	Fe1—C10—H10	125.4
C6—Fe1—C3	155.20 (12)	O1—C11—N1	122.5 (2)
C7—Fe1—C3	120.02 (11)	O1—C11—C1	122.14 (19)
C9—Fe1—C3	126.23 (12)	N1—C11—C1	115.31 (17)
C4—Fe1—C3	40.59 (9)	C13—C12—N1	125.55 (19)
C2—Fe1—C3	40.22 (9)	C13—C12—C17	119.11 (19)
C8—Fe1—C3	107.98 (10)	N1—C12—C17	115.32 (16)
C11—N1—C12	128.71 (18)	C12—C13—C14	120.5 (2)
C11—N1—H1	119.1 (16)	C12—C13—H13	119.7
C12—N1—H1	111.5 (16)	C14—C13—H13	119.7
C20—N2—C17	116.78 (17)	C15—C14—C13	121.7 (2)
C2—C1—C5	106.7 (2)	C15—C14—H14	119.2
C2—C1—C11	123.43 (18)	C13—C14—H14	119.2
C5—C1—C11	129.84 (17)	C14—C15—C16	119.8 (2)
C2—C1—Fe1	69.76 (11)	C14—C15—H15	120.1
C5—C1—Fe1	69.23 (11)	C16—C15—H15	120.1
C11—C1—Fe1	123.63 (14)	C18—C16—C17	117.39 (18)
C3—C2—C1	108.78 (19)	C18—C16—C15	123.4 (2)
C3—C2—Fe1	70.34 (12)	C17—C16—C15	119.2 (2)
C1—C2—Fe1	69.06 (11)	N2—C17—C16	122.62 (17)
C3—C2—H2	125.6	N2—C17—C12	117.68 (17)
C1—C2—H2	125.6	C16—C17—C12	119.70 (17)
Fe1—C2—H2	126.6	C19—C18—C16	119.8 (2)
C2—C3—C4	108.1 (2)	C19—C18—H18	120.1
C2—C3—Fe1	69.44 (12)	C16—C18—H18	120.1
C4—C3—Fe1	69.24 (12)	C18—C19—C20	118.7 (2)
C2—C3—H3	125.9	C18—C19—H19	120.7
C4—C3—H3	125.9	C20—C19—H19	120.7
Fe1—C3—H3	127.0	N2—C20—C19	124.65 (19)
C5—C4—C3	108.3 (2)	N2—C20—H20	117.7
C5—C4—Fe1	69.29 (12)	C19—C20—H20	117.7
C3—C4—Fe1	70.16 (12)

C10—Fe1—C1—C2	159.14 (15)	C5—Fe1—C6—C7	−167.14 (16)
C5—Fe1—C1—C2	−117.82 (19)	C1—Fe1—C6—C7	−124.89 (16)
C6—Fe1—C1—C2	117.14 (16)	C9—Fe1—C6—C7	81.22 (18)
C7—Fe1—C1—C2	75.68 (18)	C4—Fe1—C6—C7	158.4 (3)
C9—Fe1—C1—C2	−168.8 (2)	C2—Fe1—C6—C7	−81.73 (18)
C4—Fe1—C1—C2	−80.40 (15)	C8—Fe1—C6—C7	38.08 (16)
C8—Fe1—C1—C2	45.1 (4)	C3—Fe1—C6—C7	−47.0 (3)
C3—Fe1—C1—C2	−36.77 (13)	C10—C6—C7—C8	−0.3 (3)
C10—Fe1—C1—C5	−83.03 (17)	Fe1—C6—C7—C8	−60.39 (16)
C6—Fe1—C1—C5	−125.04 (14)	C10—C6—C7—Fe1	60.05 (17)
C7—Fe1—C1—C5	−166.50 (15)	C10—Fe1—C7—C8	80.21 (18)
C9—Fe1—C1—C5	−51.0 (3)	C5—Fe1—C7—C8	158.8 (3)
C4—Fe1—C1—C5	37.42 (12)	C1—Fe1—C7—C8	−167.07 (14)
C2—Fe1—C1—C5	117.82 (19)	C6—Fe1—C7—C8	118.2 (2)
C8—Fe1—C1—C5	163.0 (3)	C9—Fe1—C7—C8	37.31 (16)
C3—Fe1—C1—C5	81.05 (14)	C4—Fe1—C7—C8	−47.7 (3)
C10—Fe1—C1—C11	41.8 (2)	C2—Fe1—C7—C8	−124.92 (16)
C5—Fe1—C1—C11	124.8 (2)	C3—Fe1—C7—C8	−82.58 (17)
C6—Fe1—C1—C11	−0.25 (19)	C10—Fe1—C7—C6	−37.94 (17)
C7—Fe1—C1—C11	−41.7 (2)	C5—Fe1—C7—C6	40.7 (4)
C9—Fe1—C1—C11	73.8 (3)	C1—Fe1—C7—C6	74.78 (18)
C4—Fe1—C1—C11	162.22 (18)	C9—Fe1—C7—C6	−80.84 (18)
C2—Fe1—C1—C11	−117.4 (2)	C4—Fe1—C7—C6	−165.9 (2)
C8—Fe1—C1—C11	−72.3 (4)	C2—Fe1—C7—C6	116.93 (17)
C3—Fe1—C1—C11	−154.15 (18)	C8—Fe1—C7—C6	−118.2 (2)
C5—C1—C2—C3	−0.4 (2)	C3—Fe1—C7—C6	159.27 (16)
C11—C1—C2—C3	176.95 (18)	C6—C7—C8—C9	0.3 (3)
Fe1—C1—C2—C3	59.31 (14)	Fe1—C7—C8—C9	−59.66 (17)
C5—C1—C2—Fe1	−59.67 (13)	C6—C7—C8—Fe1	59.97 (16)
C11—C1—C2—Fe1	117.64 (18)	C10—Fe1—C8—C9	36.84 (19)
C10—Fe1—C2—C3	−169.1 (2)	C5—Fe1—C8—C9	−47.9 (3)
C5—Fe1—C2—C3	−81.27 (14)	C1—Fe1—C8—C9	158.4 (3)
C1—Fe1—C2—C3	−120.17 (18)	C6—Fe1—C8—C9	80.49 (19)
C6—Fe1—C2—C3	158.25 (14)	C7—Fe1—C8—C9	118.9 (2)
C7—Fe1—C2—C3	115.40 (16)	C4—Fe1—C8—C9	−82.8 (2)
C9—Fe1—C2—C3	43.8 (4)	C2—Fe1—C8—C9	−166.38 (17)
C4—Fe1—C2—C3	−37.43 (13)	C3—Fe1—C8—C9	−125.57 (18)
C8—Fe1—C2—C3	74.31 (18)	C10—Fe1—C8—C7	−82.11 (19)
C10—Fe1—C2—C1	−48.9 (3)	C5—Fe1—C8—C7	−166.9 (2)
C5—Fe1—C2—C1	38.90 (13)	C1—Fe1—C8—C7	39.4 (4)
C6—Fe1—C2—C1	−81.57 (16)	C6—Fe1—C8—C7	−38.46 (16)
C7—Fe1—C2—C1	−124.43 (16)	C9—Fe1—C8—C7	−118.9 (2)
C9—Fe1—C2—C1	164.0 (3)	C4—Fe1—C8—C7	158.25 (16)
C4—Fe1—C2—C1	82.75 (14)	C2—Fe1—C8—C7	74.68 (19)
C8—Fe1—C2—C1	−165.52 (15)	C3—Fe1—C8—C7	115.49 (17)
C3—Fe1—C2—C1	120.17 (18)	C7—C8—C9—C10	−0.2 (3)
C1—C2—C3—C4	0.1 (2)	Fe1—C8—C9—C10	−59.46 (18)
Fe1—C2—C3—C4	58.59 (15)	C7—C8—C9—Fe1	59.30 (16)
C1—C2—C3—Fe1	−58.52 (14)	C5—Fe1—C9—C10	−82.30 (19)
C10—Fe1—C3—C2	164.9 (3)	C1—Fe1—C9—C10	−45.7 (3)
C5—Fe1—C3—C2	82.30 (13)	C6—Fe1—C9—C10	37.51 (17)
C1—Fe1—C3—C2	37.62 (12)	C7—Fe1—C9—C10	81.92 (19)
C6—Fe1—C3—C2	−49.2 (3)	C4—Fe1—C9—C10	−125.21 (17)
C7—Fe1—C3—C2	−82.63 (16)	C2—Fe1—C9—C10	159.7 (3)
C9—Fe1—C3—C2	−165.24 (14)	C8—Fe1—C9—C10	119.8 (3)
C4—Fe1—C3—C2	119.84 (19)	C3—Fe1—C9—C10	−166.61 (16)
C8—Fe1—C3—C2	−125.11 (15)	C10—Fe1—C9—C8	−119.8 (3)
C10—Fe1—C3—C4	45.1 (4)	C5—Fe1—C9—C8	157.87 (17)
C5—Fe1—C3—C4	−37.54 (14)	C1—Fe1—C9—C8	−165.6 (2)
C1—Fe1—C3—C4	−82.22 (15)	C6—Fe1—C9—C8	−82.32 (19)
C6—Fe1—C3—C4	−169.0 (2)	C7—Fe1—C9—C8	−37.91 (18)
C7—Fe1—C3—C4	157.53 (16)	C4—Fe1—C9—C8	114.96 (18)
C9—Fe1—C3—C4	74.93 (18)	C2—Fe1—C9—C8	39.9 (4)
C2—Fe1—C3—C4	−119.84 (19)	C3—Fe1—C9—C8	73.6 (2)
C8—Fe1—C3—C4	115.05 (16)	C8—C9—C10—C6	−0.1 (3)
C2—C3—C4—C5	0.3 (2)	Fe1—C9—C10—C6	−59.78 (17)
Fe1—C3—C4—C5	58.97 (15)	C8—C9—C10—Fe1	59.72 (18)
C2—C3—C4—Fe1	−58.72 (15)	C7—C6—C10—C9	0.3 (3)
C10—Fe1—C4—C5	75.47 (18)	Fe1—C6—C10—C9	60.15 (18)
C1—Fe1—C4—C5	−38.14 (12)	C7—C6—C10—Fe1	−59.90 (16)
C6—Fe1—C4—C5	44.4 (4)	C5—Fe1—C10—C9	115.56 (16)
C7—Fe1—C4—C5	−169.1 (2)	C1—Fe1—C10—C9	159.40 (15)
C9—Fe1—C4—C5	115.51 (15)	C6—Fe1—C10—C9	−119.5 (2)
C2—Fe1—C4—C5	−82.48 (14)	C7—Fe1—C10—C9	−80.97 (18)
C8—Fe1—C4—C5	157.37 (14)	C4—Fe1—C10—C9	73.90 (19)
C3—Fe1—C4—C5	−119.6 (2)	C2—Fe1—C10—C9	−165.3 (2)
C10—Fe1—C4—C3	−164.95 (16)	C8—Fe1—C10—C9	−37.05 (16)
C5—Fe1—C4—C3	119.6 (2)	C3—Fe1—C10—C9	39.1 (4)
C1—Fe1—C4—C3	81.44 (15)	C5—Fe1—C10—C6	−124.94 (17)
C6—Fe1—C4—C3	164.0 (3)	C1—Fe1—C10—C6	−81.10 (18)
C7—Fe1—C4—C3	−49.6 (3)	C7—Fe1—C10—C6	38.53 (17)
C9—Fe1—C4—C3	−124.92 (16)	C9—Fe1—C10—C6	119.5 (2)
C2—Fe1—C4—C3	37.09 (13)	C4—Fe1—C10—C6	−166.60 (16)
C8—Fe1—C4—C3	−83.05 (17)	C2—Fe1—C10—C6	−45.8 (3)
C3—C4—C5—C1	−0.5 (2)	C8—Fe1—C10—C6	82.45 (19)
Fe1—C4—C5—C1	59.03 (14)	C3—Fe1—C10—C6	158.6 (3)
C3—C4—C5—Fe1	−59.52 (15)	C12—N1—C11—O1	5.3 (3)
C2—C1—C5—C4	0.5 (2)	C12—N1—C11—C1	−174.16 (18)
C11—C1—C5—C4	−176.56 (19)	C2—C1—C11—O1	6.2 (3)
Fe1—C1—C5—C4	−59.49 (15)	C5—C1—C11—O1	−177.1 (2)
C2—C1—C5—Fe1	60.01 (13)	Fe1—C1—C11—O1	92.8 (2)
C11—C1—C5—Fe1	−117.1 (2)	C2—C1—C11—N1	−174.32 (18)
C10—Fe1—C5—C4	−124.51 (17)	C5—C1—C11—N1	2.3 (3)
C1—Fe1—C5—C4	119.40 (18)	Fe1—C1—C11—N1	−87.69 (19)
C6—Fe1—C5—C4	−165.47 (16)	C11—N1—C12—C13	−8.9 (3)
C7—Fe1—C5—C4	162.7 (3)	C11—N1—C12—C17	169.84 (19)
C9—Fe1—C5—C4	−82.90 (17)	N1—C12—C13—C14	179.05 (19)
C2—Fe1—C5—C4	80.77 (15)	C17—C12—C13—C14	0.4 (3)
C8—Fe1—C5—C4	−49.6 (3)	C12—C13—C14—C15	−1.0 (3)
C3—Fe1—C5—C4	37.46 (14)	C13—C14—C15—C16	0.6 (3)
C10—Fe1—C5—C1	116.08 (15)	C14—C15—C16—C18	−178.2 (2)
C6—Fe1—C5—C1	75.13 (16)	C14—C15—C16—C17	0.5 (3)
C7—Fe1—C5—C1	43.3 (4)	C20—N2—C17—C16	1.9 (3)
C9—Fe1—C5—C1	157.69 (15)	C20—N2—C17—C12	−177.45 (17)
C4—Fe1—C5—C1	−119.40 (18)	C18—C16—C17—N2	−1.8 (3)
C2—Fe1—C5—C1	−38.63 (13)	C15—C16—C17—N2	179.49 (18)
C8—Fe1—C5—C1	−169.0 (2)	C18—C16—C17—C12	177.61 (17)
C3—Fe1—C5—C1	−81.94 (14)	C15—C16—C17—C12	−1.1 (3)
C5—Fe1—C6—C10	74.7 (2)	C13—C12—C17—N2	−179.88 (17)
C1—Fe1—C6—C10	116.98 (17)	N1—C12—C17—N2	1.3 (2)
C7—Fe1—C6—C10	−118.1 (2)	C13—C12—C17—C16	0.7 (3)
C9—Fe1—C6—C10	−36.91 (16)	N1—C12—C17—C16	−178.11 (16)
C4—Fe1—C6—C10	40.3 (4)	C17—C16—C18—C19	−0.1 (3)
C2—Fe1—C6—C10	160.14 (15)	C15—C16—C18—C19	178.6 (2)
C8—Fe1—C6—C10	−80.05 (18)	C16—C18—C19—C20	1.7 (3)
C3—Fe1—C6—C10	−165.1 (2)	C17—N2—C20—C19	−0.2 (3)
C10—Fe1—C6—C7	118.1 (2)	C18—C19—C20—N2	−1.6 (3)

Experimental details

Crystal data
Chemical formula	[Fe(C₅H₅)(C₁₅H₁₁N₂O)]
M_r	356.20
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	296
a, b, c (Å)	10.1680 (17), 12.133 (2), 26.079 (4)
V (Å³)	3217.4 (10)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.95
Crystal size (mm)	0.46 × 0.37 × 0.25

Data collection
Diffractometer	Rigaku Mercury CCD diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2000)
T_min, T_max	0.668, 0.795
No. of measured, independent and observed [I > 2σ(I)] reflections	18658, 3940, 2996
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.666

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.097, 1.01
No. of reflections	3940
No. of parameters	222
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.37

Computer programs: CrystalClear (Rigaku, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

We gratefully acknowledge financial support from the Foundation of Henan Educational Committee (2011B150001) and the Foundation of Henan University of Urban Construction (2010JYB007).

References

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