{1-[(3,5-Dimethyl-4H-1,2,4-triazol-4-yl)imino]eth­yl}ferrocene

Hao, X.-Q.; Liang, D.-S.; Liu, R.-Y.; Gong, J.-F.; Song, M.-P.

doi:10.1107/S1600536808028973

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 10| October 2008| Page m1275

doi:10.1107/S1600536808028973

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{1-[(3,5-Dimethyl-4H-1,2,4-triazol-4-yl)imino]ethyl}ferrocene

Xin-Qi Hao,^a Dong-Song Liang,^b Ruo-Yi Liu,^a Jun-Fang Gong ^a and Mao-Ping Song ^a ^*

^aDepartment of Chemistry, Henan Key Laboratory of Chemical Biology and Organic Chemistry, Zhengzhou University, Zhengzhou 450052, People's Republic of China, and ^bCollege of Materials Science and Engineering, Zhengzhou University, Zhengzhou 450052, People's Republic of China
^*Correspondence e-mail: maopingsong@zzu.edu.cn

(Received 21 August 2008; accepted 10 September 2008; online 17 September 2008)

In the title compound, [Fe(C₅H₅)(C₁₁H₁₃N₄)], the triazolyl and Cp ring form a dihedral angle of 76.6 (3)°. In the crystal structure, there are both intra- and intermolecular C—H⋯π interactions, forming a one-dimensional chain structure along [010].

Related literature

For related literature, see: Hao et al. (2007 ); Huo et al. (1994 ); Wu et al. (2001 ).

Experimental

Crystal data

[Fe(C₅H₅)(C₁₁H₁₃N₄)]
M_r = 322.19
Monoclinic, P 2₁ /c
a = 8.7851 (18) Å
b = 13.271 (3) Å
c = 13.035 (3) Å
β = 104.49 (3)°
V = 1471.4 (5) Å³
Z = 4
Mo Kα radiation
μ = 1.02 mm⁻¹
T = 293 (2) K
0.30 × 0.26 × 0.20 mm

Data collection

Rigaku Saturn724 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.749, T_max = 0.822
14449 measured reflections
2583 independent reflections
2485 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.029
wR(F²) = 0.068
S = 1.09
2583 reflections
193 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯Cg1	0.98	2.52	3.255 (3)	132
C5—H5⋯Cg3ⁱ	0.98	2.87	3.703 (5)	144
Symmetry code: (i) $[x, -y-{\script{1\over 2}}, z-{\script{1\over 2}}]$ . Cg1 and Cg3 are the centroids of the triazolyl ring and the Cp rings C6–C10, respectively.

Data collection: CrystalClear (Rigaku/MSC, 2006 ); 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: Bruker SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808028973/si2106sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808028973/si2106Isup2.hkl

checkCIF report

Comment top

During the past decades, we have systematically studied the cyclometallation reaction of Schiff base type of ferrocenylimines (Huo et al., 1994; Wu et al., 2001). Following these work, here we report the synthesis, characterization and crystal structure of the title ferrocenylimine ligand.

A view of the molecular structure of the title compound is given in Fig. 1. All the bond distances and angles are within normal ranges, the C11—N1 distance [1.290 (2) Å] is similar to those of the related complex (Hao et al., 2007) and the C11—N1—N2 angle is 115.15 (16)°. The triazolyl and Cp ring form a dihedral angle of 103.4 (3)°. Fig. 2 and Table 1 shows that in the crystal there exist intra- and intermolecular C—H···π interactions: H6···Cg1 = 2.519 Å [symmetry code for Cg1 (x, y, z), intra], and H5···Cg3 = 2.868 Å; symmetry code for Cg3 (x, -1/2 - y, -1/2 + z)]. Cg1 and Cg3 are the centroids of the triazolyl and one of the Cp rings C6–C10, respectively], which are attributed to construct the one-dimensional chain structure of the title compound. Partial stacking between neighbouring ferrocene units via inversion centres is shown in Fig. 3. The partial π–π stacking interactions are found between Cg2 and Cg2ⁱ [symmetry code i = (-x, -y, 2 - z)], with a distance 3.8525 (18) Å, the perpendicular distance is 3.295 Å with a slippage of 1.829 Å. Cg2 is the centroid of the Cp ring C1–C5.

Related literature top

For related literature, see: Hao et al. (2007); Huo et al. (1994); Wu et al. (2001). Cg1 and Cg3 are the centroids of the triazolyl ring and the Cp rings C6–C10, respectively.

Experimental top

Acetylferrocene (1 mmol) was dissolved in anhydrous toluene (40 ml) and 3,5-dimethyl-4-amino-4H-1,2,4-triazole (1.5 mmol) was added. The red solution was refluxed under argon atmosphere for about 3 days. Every day an addition of small quantities of activated Al₂O₃ was necessary to complete the reaction. The hot solution was carefully filtered, and the filtrate was concentrated to dryness in a rotary evaporator. The residue was purified by passing through a silica gel column with CH₂Cl₂ as eluent, giving the title compound, which was recrystallized from dichloromethane–petroleum ether solution at room temperature to give the desired product as colorless crystals suitable for single-crystal X-ray diffraction (yield 25%; m.p: 440 K-443 K). IR data (v_max/ cm^-1): 1591, 1569, 1531, 1479, 1409, 1307, 1104, 1005, 827, 762. NMR δ(H) 4.87 (2H, s), 4.59 (2H, s), 4.25 (5H, s), 2.35 (6H, s), 2.07 (3H, s). MS-ESI⁺ [m/z]: 323 (M+H), 345 (M+Na), 667 (2M+Na).

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2006); cell refinement: CrystalClear (Rigaku/MSC, 2006); data reduction: CrystalClear (Rigaku/MSC, 2006); 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.
	Fig. 2. Partial view of the crystal packing showing the formation of the 1D chain structure formed by the C—H···π interactions.
	Fig. 3. Section of the crystal packing viewed down [100].

{1-[(3,5-Dimethyl-4H-1,2,4-triazol-4-yl)imino]ethyl}ferrocene top

Crystal data top

[Fe(C₅H₅)(C₁₁H₁₃N₄)]	F(000) = 672
M_r = 322.19	D_x = 1.454 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.7851 (18) Å	Cell parameters from 4008 reflections
b = 13.271 (3) Å	θ = 2.5–26.1°
c = 13.035 (3) Å	µ = 1.02 mm⁻¹
β = 104.49 (3)°	T = 293 K
V = 1471.4 (5) Å³	Block, red
Z = 4	0.30 × 0.26 × 0.20 mm

Data collection top

Rigaku/MSC MODEL? CCD area-detector diffractometer	2583 independent reflections
Radiation source: fine-focus sealed tube	2485 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ϕ and ω scans	θ_max = 25.0°, θ_min = 3.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
T_min = 0.749, T_max = 0.822	k = −15→15
14449 measured reflections	l = −15→15

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.068	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.031P)² + 0.6853P] where P = (F_o² + 2F_c²)/3
2583 reflections	(Δ/σ)_max = 0.001
193 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

[Fe(C₅H₅)(C₁₁H₁₃N₄)]	V = 1471.4 (5) Å³
M_r = 322.19	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.7851 (18) Å	µ = 1.02 mm⁻¹
b = 13.271 (3) Å	T = 293 K
c = 13.035 (3) Å	0.30 × 0.26 × 0.20 mm
β = 104.49 (3)°

Data collection top

Rigaku/MSC MODEL? CCD area-detector diffractometer	2583 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2485 reflections with I > 2σ(I)
T_min = 0.749, T_max = 0.822	R_int = 0.026
14449 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	0 restraints
wR(F²) = 0.068	H-atom parameters constrained
S = 1.09	Δρ_max = 0.22 e Å⁻³
2583 reflections	Δρ_min = −0.18 e Å⁻³
193 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	0.14717 (3)	0.155436 (19)	0.83336 (2)	0.02657 (10)
N1	0.36589 (18)	0.41476 (13)	0.94499 (13)	0.0366 (4)
N2	0.49929 (18)	0.37952 (13)	0.91279 (13)	0.0351 (4)
N3	0.7280 (2)	0.31235 (17)	0.92302 (18)	0.0566 (5)
N4	0.6890 (2)	0.37255 (17)	0.83286 (17)	0.0538 (5)
C1	0.2665 (3)	0.06374 (16)	0.95248 (17)	0.0456 (5)
H1	0.3811	0.0571	0.9763	0.055*
C2	0.1664 (3)	0.00600 (16)	0.87231 (18)	0.0454 (5)
H2	0.1988	−0.0480	0.8310	0.054*
C3	0.0112 (3)	0.03956 (17)	0.86285 (19)	0.0482 (6)
H3	−0.0834	0.0131	0.8135	0.058*
C4	0.0157 (3)	0.11866 (18)	0.93709 (19)	0.0498 (6)
H4	−0.0749	0.1562	0.9482	0.060*
C5	0.1738 (3)	0.13290 (17)	0.99218 (17)	0.0469 (6)
H5	0.2127	0.1826	1.0482	0.056*
C6	0.3048 (2)	0.23320 (14)	0.77318 (15)	0.0302 (4)
H6	0.4194	0.2305	0.7996	0.036*
C7	0.2125 (2)	0.17029 (15)	0.69381 (15)	0.0346 (4)
H7	0.2523	0.1162	0.6564	0.042*
C8	0.0526 (2)	0.19765 (16)	0.67915 (15)	0.0360 (5)
H8	−0.0371	0.1655	0.6300	0.043*
C9	0.0439 (2)	0.27709 (14)	0.74964 (15)	0.0324 (4)
H9	−0.0528	0.3100	0.7568	0.039*
C10	0.2013 (2)	0.30161 (13)	0.80928 (14)	0.0260 (4)
C11	0.2331 (2)	0.37758 (14)	0.89329 (14)	0.0270 (4)
C12	0.0945 (2)	0.42209 (15)	0.92519 (16)	0.0359 (4)
H12A	0.1309	0.4672	0.9838	0.054*
H12B	0.0338	0.3691	0.9457	0.054*
H12C	0.0301	0.4585	0.8665	0.054*
C13	0.6131 (2)	0.31904 (17)	0.97039 (19)	0.0440 (5)
C14	0.6040 (3)	0.2679 (2)	1.0694 (2)	0.0640 (7)
H14A	0.6814	0.2153	1.0854	0.096*
H14B	0.5011	0.2394	1.0608	0.096*
H14C	0.6236	0.3158	1.1264	0.096*
C15	0.5514 (2)	0.41269 (16)	0.82868 (17)	0.0402 (5)
C16	0.4626 (3)	0.48245 (19)	0.7469 (2)	0.0550 (6)
H16A	0.5297	0.5061	0.7042	0.083*
H16B	0.4264	0.5387	0.7806	0.083*
H16C	0.3740	0.4478	0.7030	0.083*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe1	0.02826 (16)	0.02453 (16)	0.02769 (16)	−0.00021 (11)	0.00847 (11)	0.00028 (11)
N1	0.0289 (8)	0.0381 (10)	0.0449 (10)	−0.0003 (7)	0.0130 (7)	−0.0112 (8)
N2	0.0232 (8)	0.0385 (9)	0.0442 (10)	−0.0042 (7)	0.0098 (7)	−0.0095 (8)
N3	0.0298 (10)	0.0669 (13)	0.0758 (15)	0.0070 (9)	0.0181 (10)	0.0068 (12)
N4	0.0339 (10)	0.0674 (14)	0.0661 (14)	−0.0006 (9)	0.0237 (9)	0.0013 (11)
C1	0.0567 (14)	0.0391 (12)	0.0384 (12)	0.0102 (10)	0.0072 (10)	0.0107 (10)
C2	0.0691 (15)	0.0249 (10)	0.0455 (12)	0.0014 (10)	0.0208 (11)	0.0024 (9)
C3	0.0534 (14)	0.0409 (12)	0.0550 (14)	−0.0139 (11)	0.0223 (11)	0.0045 (11)
C4	0.0596 (15)	0.0439 (13)	0.0588 (15)	0.0053 (11)	0.0393 (13)	0.0130 (12)
C5	0.0758 (17)	0.0389 (12)	0.0298 (11)	0.0017 (11)	0.0202 (11)	0.0021 (9)
C6	0.0281 (9)	0.0323 (10)	0.0325 (10)	−0.0012 (8)	0.0116 (8)	−0.0007 (8)
C7	0.0439 (11)	0.0349 (11)	0.0274 (10)	−0.0011 (9)	0.0136 (9)	−0.0021 (8)
C8	0.0378 (11)	0.0371 (11)	0.0284 (10)	−0.0042 (9)	−0.0006 (8)	0.0025 (9)
C9	0.0277 (9)	0.0308 (10)	0.0362 (10)	0.0014 (8)	0.0033 (8)	0.0055 (8)
C10	0.0249 (9)	0.0247 (9)	0.0295 (9)	0.0008 (7)	0.0088 (7)	0.0040 (8)
C11	0.0262 (9)	0.0251 (9)	0.0315 (10)	0.0002 (7)	0.0104 (8)	0.0034 (8)
C12	0.0314 (10)	0.0386 (11)	0.0397 (11)	0.0054 (9)	0.0125 (9)	−0.0026 (9)
C13	0.0271 (10)	0.0469 (13)	0.0550 (14)	−0.0032 (9)	0.0050 (10)	−0.0010 (11)
C14	0.0489 (14)	0.0784 (19)	0.0629 (16)	0.0037 (13)	0.0106 (12)	0.0135 (15)
C15	0.0291 (10)	0.0438 (12)	0.0490 (12)	−0.0102 (9)	0.0122 (9)	−0.0073 (10)
C16	0.0437 (13)	0.0599 (15)	0.0623 (15)	−0.0071 (11)	0.0150 (12)	0.0090 (13)

Geometric parameters (Å, º) top

Fe1—C9	2.0310 (19)	C4—H4	0.9800
Fe1—C6	2.0350 (19)	C5—H5	0.9800
Fe1—C10	2.0402 (18)	C6—C7	1.416 (3)
Fe1—C3	2.042 (2)	C6—C10	1.444 (3)
Fe1—C2	2.044 (2)	C6—H6	0.9800
Fe1—C1	2.044 (2)	C7—C8	1.417 (3)
Fe1—C4	2.045 (2)	C7—H7	0.9800
Fe1—C5	2.046 (2)	C8—C9	1.413 (3)
Fe1—C7	2.0494 (19)	C8—H8	0.9800
Fe1—C8	2.051 (2)	C9—C10	1.444 (3)
N1—C11	1.290 (2)	C9—H9	0.9800
N1—N2	1.419 (2)	C10—C11	1.463 (3)
N2—C13	1.354 (3)	C11—C12	1.503 (2)
N2—C15	1.363 (3)	C12—H12A	0.9600
N3—C13	1.311 (3)	C12—H12B	0.9600
N3—N4	1.391 (3)	C12—H12C	0.9600
N4—C15	1.310 (3)	C13—C14	1.479 (3)
C1—C5	1.409 (3)	C14—H14A	0.9600
C1—C2	1.412 (3)	C14—H14B	0.9600
C1—H1	0.9800	C14—H14C	0.9600
C2—C3	1.410 (3)	C15—C16	1.478 (3)
C2—H2	0.9800	C16—H16A	0.9600
C3—C4	1.421 (3)	C16—H16B	0.9600
C3—H3	0.9800	C16—H16C	0.9600
C4—C5	1.407 (4)

C9—Fe1—C6	69.23 (8)	C5—C4—C3	107.6 (2)
C9—Fe1—C10	41.54 (7)	C5—C4—Fe1	69.94 (12)
C6—Fe1—C10	41.52 (7)	C3—C4—Fe1	69.53 (12)
C9—Fe1—C3	119.75 (9)	C5—C4—H4	126.2
C6—Fe1—C3	160.23 (9)	C3—C4—H4	126.2
C10—Fe1—C3	156.19 (9)	Fe1—C4—H4	126.2
C9—Fe1—C2	154.55 (9)	C4—C5—C1	108.2 (2)
C6—Fe1—C2	124.47 (9)	C4—C5—Fe1	69.82 (13)
C10—Fe1—C2	162.36 (9)	C1—C5—Fe1	69.75 (12)
C3—Fe1—C2	40.38 (9)	C4—C5—H5	125.9
C9—Fe1—C1	163.11 (9)	C1—C5—H5	125.9
C6—Fe1—C1	109.00 (9)	Fe1—C5—H5	125.9
C10—Fe1—C1	126.01 (9)	C7—C6—C10	108.47 (16)
C3—Fe1—C1	67.77 (10)	C7—C6—Fe1	70.26 (11)
C2—Fe1—C1	40.41 (9)	C10—C6—Fe1	69.43 (10)
C9—Fe1—C4	107.15 (9)	C7—C6—H6	125.8
C6—Fe1—C4	158.00 (9)	C10—C6—H6	125.8
C10—Fe1—C4	121.37 (8)	Fe1—C6—H6	125.8
C3—Fe1—C4	40.71 (10)	C6—C7—C8	108.32 (17)
C2—Fe1—C4	68.24 (9)	C6—C7—Fe1	69.17 (11)
C1—Fe1—C4	67.84 (10)	C8—C7—Fe1	69.87 (11)
C9—Fe1—C5	125.62 (9)	C6—C7—H7	125.8
C6—Fe1—C5	123.19 (9)	C8—C7—H7	125.8
C10—Fe1—C5	108.82 (8)	Fe1—C7—H7	125.8
C3—Fe1—C5	67.89 (10)	C9—C8—C7	108.47 (17)
C2—Fe1—C5	68.00 (9)	C9—C8—Fe1	68.98 (11)
C1—Fe1—C5	40.30 (9)	C7—C8—Fe1	69.71 (11)
C4—Fe1—C5	40.24 (10)	C9—C8—H8	125.8
C9—Fe1—C7	68.49 (8)	C7—C8—H8	125.8
C6—Fe1—C7	40.57 (8)	Fe1—C8—H8	125.8
C10—Fe1—C7	69.16 (8)	C8—C9—C10	108.53 (17)
C3—Fe1—C7	123.13 (9)	C8—C9—Fe1	70.53 (11)
C2—Fe1—C7	106.84 (8)	C10—C9—Fe1	69.57 (10)
C1—Fe1—C7	121.81 (9)	C8—C9—H9	125.7
C4—Fe1—C7	160.03 (10)	C10—C9—H9	125.7
C5—Fe1—C7	157.74 (10)	Fe1—C9—H9	125.7
C9—Fe1—C8	40.50 (8)	C9—C10—C6	106.20 (16)
C6—Fe1—C8	68.38 (8)	C9—C10—C11	122.42 (16)
C10—Fe1—C8	69.05 (8)	C6—C10—C11	131.23 (16)
C3—Fe1—C8	106.12 (9)	C9—C10—Fe1	68.89 (10)
C2—Fe1—C8	119.77 (9)	C6—C10—Fe1	69.05 (10)
C1—Fe1—C8	155.79 (9)	C11—C10—Fe1	123.25 (13)
C4—Fe1—C8	123.78 (10)	N1—C11—C10	129.26 (17)
C5—Fe1—C8	161.24 (9)	N1—C11—C12	113.23 (16)
C7—Fe1—C8	40.43 (8)	C10—C11—C12	117.50 (16)
C11—N1—N2	115.15 (16)	C11—C12—H12A	109.5
C13—N2—C15	106.71 (17)	C11—C12—H12B	109.5
C13—N2—N1	125.56 (18)	H12A—C12—H12B	109.5
C15—N2—N1	126.86 (17)	C11—C12—H12C	109.5
C13—N3—N4	107.64 (18)	H12A—C12—H12C	109.5
C15—N4—N3	107.37 (18)	H12B—C12—H12C	109.5
C5—C1—C2	108.4 (2)	N3—C13—N2	109.1 (2)
C5—C1—Fe1	69.95 (12)	N3—C13—C14	126.6 (2)
C2—C1—Fe1	69.79 (12)	N2—C13—C14	124.2 (2)
C5—C1—H1	125.8	C13—C14—H14A	109.5
C2—C1—H1	125.8	C13—C14—H14B	109.5
Fe1—C1—H1	125.8	H14A—C14—H14B	109.5
C3—C2—C1	107.6 (2)	C13—C14—H14C	109.5
C3—C2—Fe1	69.74 (12)	H14A—C14—H14C	109.5
C1—C2—Fe1	69.80 (12)	H14B—C14—H14C	109.5
C3—C2—H2	126.2	N4—C15—N2	109.1 (2)
C1—C2—H2	126.2	N4—C15—C16	126.8 (2)
Fe1—C2—H2	126.2	N2—C15—C16	124.03 (19)
C2—C3—C4	108.2 (2)	C15—C16—H16A	109.5
C2—C3—Fe1	69.88 (12)	C15—C16—H16B	109.5
C4—C3—Fe1	69.76 (12)	H16A—C16—H16B	109.5
C2—C3—H3	125.9	C15—C16—H16C	109.5
C4—C3—H3	125.9	H16A—C16—H16C	109.5
Fe1—C3—H3	125.9	H16B—C16—H16C	109.5

C11—N1—N2—C13	−110.8 (2)	C8—Fe1—C6—C10	82.38 (12)
C11—N1—N2—C15	81.3 (2)	C10—C6—C7—C8	0.0 (2)
C13—N3—N4—C15	−0.5 (3)	Fe1—C6—C7—C8	59.08 (14)
C9—Fe1—C1—C5	38.3 (4)	C10—C6—C7—Fe1	−59.11 (13)
C6—Fe1—C1—C5	119.29 (15)	C9—Fe1—C7—C6	82.77 (12)
C10—Fe1—C1—C5	76.07 (17)	C10—Fe1—C7—C6	38.07 (11)
C3—Fe1—C1—C5	−81.56 (16)	C3—Fe1—C7—C6	−164.92 (12)
C2—Fe1—C1—C5	−119.4 (2)	C2—Fe1—C7—C6	−123.76 (12)
C4—Fe1—C1—C5	−37.43 (15)	C1—Fe1—C7—C6	−82.21 (14)
C7—Fe1—C1—C5	162.25 (14)	C4—Fe1—C7—C6	163.8 (2)
C8—Fe1—C1—C5	−161.34 (19)	C5—Fe1—C7—C6	−50.8 (3)
C9—Fe1—C1—C2	157.8 (3)	C8—Fe1—C7—C6	119.84 (17)
C6—Fe1—C1—C2	−121.27 (14)	C9—Fe1—C7—C8	−37.08 (12)
C10—Fe1—C1—C2	−164.49 (12)	C6—Fe1—C7—C8	−119.84 (17)
C3—Fe1—C1—C2	37.87 (14)	C10—Fe1—C7—C8	−81.77 (12)
C4—Fe1—C1—C2	82.01 (15)	C3—Fe1—C7—C8	75.24 (15)
C5—Fe1—C1—C2	119.4 (2)	C2—Fe1—C7—C8	116.40 (13)
C7—Fe1—C1—C2	−78.31 (16)	C1—Fe1—C7—C8	157.95 (12)
C8—Fe1—C1—C2	−41.9 (3)	C4—Fe1—C7—C8	43.9 (3)
C5—C1—C2—C3	−0.2 (2)	C5—Fe1—C7—C8	−170.7 (2)
Fe1—C1—C2—C3	−59.72 (15)	C6—C7—C8—C9	−0.4 (2)
C5—C1—C2—Fe1	59.54 (15)	Fe1—C7—C8—C9	58.21 (14)
C9—Fe1—C2—C3	−46.5 (3)	C6—C7—C8—Fe1	−58.65 (13)
C6—Fe1—C2—C3	−162.68 (13)	C6—Fe1—C8—C9	−82.91 (12)
C10—Fe1—C2—C3	164.2 (2)	C10—Fe1—C8—C9	−38.20 (11)
C1—Fe1—C2—C3	118.7 (2)	C3—Fe1—C8—C9	117.18 (13)
C4—Fe1—C2—C3	37.77 (15)	C2—Fe1—C8—C9	158.75 (12)
C5—Fe1—C2—C3	81.29 (16)	C1—Fe1—C8—C9	−171.3 (2)
C7—Fe1—C2—C3	−121.70 (14)	C4—Fe1—C8—C9	76.29 (15)
C8—Fe1—C2—C3	−79.70 (16)	C5—Fe1—C8—C9	48.7 (3)
C9—Fe1—C2—C1	−165.18 (18)	C7—Fe1—C8—C9	−120.27 (17)
C6—Fe1—C2—C1	78.62 (16)	C9—Fe1—C8—C7	120.27 (17)
C10—Fe1—C2—C1	45.5 (3)	C6—Fe1—C8—C7	37.36 (11)
C3—Fe1—C2—C1	−118.7 (2)	C10—Fe1—C8—C7	82.06 (12)
C4—Fe1—C2—C1	−80.92 (15)	C3—Fe1—C8—C7	−122.55 (13)
C5—Fe1—C2—C1	−37.41 (14)	C2—Fe1—C8—C7	−80.99 (14)
C7—Fe1—C2—C1	119.60 (14)	C1—Fe1—C8—C7	−51.1 (3)
C8—Fe1—C2—C1	161.61 (13)	C4—Fe1—C8—C7	−163.44 (12)
C1—C2—C3—C4	0.3 (2)	C5—Fe1—C8—C7	169.0 (2)
Fe1—C2—C3—C4	−59.46 (15)	C7—C8—C9—C10	0.7 (2)
C1—C2—C3—Fe1	59.75 (15)	Fe1—C8—C9—C10	59.40 (13)
C9—Fe1—C3—C2	158.96 (13)	C7—C8—C9—Fe1	−58.66 (14)
C6—Fe1—C3—C2	46.5 (3)	C6—Fe1—C9—C8	80.65 (12)
C10—Fe1—C3—C2	−168.23 (18)	C10—Fe1—C9—C8	119.43 (16)
C1—Fe1—C3—C2	−37.90 (14)	C3—Fe1—C9—C8	−79.82 (14)
C4—Fe1—C3—C2	−119.3 (2)	C2—Fe1—C9—C8	−47.1 (2)
C5—Fe1—C3—C2	−81.58 (15)	C1—Fe1—C9—C8	167.7 (3)
C7—Fe1—C3—C2	76.51 (16)	C4—Fe1—C9—C8	−122.32 (13)
C8—Fe1—C3—C2	117.25 (14)	C5—Fe1—C9—C8	−162.70 (13)
C9—Fe1—C3—C4	−81.75 (16)	C7—Fe1—C9—C8	37.01 (12)
C6—Fe1—C3—C4	165.8 (2)	C6—Fe1—C9—C10	−38.79 (11)
C10—Fe1—C3—C4	−48.9 (3)	C3—Fe1—C9—C10	160.74 (11)
C2—Fe1—C3—C4	119.3 (2)	C2—Fe1—C9—C10	−166.50 (17)
C1—Fe1—C3—C4	81.39 (16)	C1—Fe1—C9—C10	48.3 (3)
C5—Fe1—C3—C4	37.71 (14)	C4—Fe1—C9—C10	118.25 (12)
C7—Fe1—C3—C4	−164.21 (14)	C5—Fe1—C9—C10	77.86 (14)
C8—Fe1—C3—C4	−123.46 (15)	C7—Fe1—C9—C10	−82.42 (12)
C2—C3—C4—C5	−0.3 (2)	C8—Fe1—C9—C10	−119.43 (16)
Fe1—C3—C4—C5	−59.83 (15)	C8—C9—C10—C6	−0.8 (2)
C2—C3—C4—Fe1	59.54 (15)	Fe1—C9—C10—C6	59.25 (12)
C9—Fe1—C4—C5	−125.37 (13)	C8—C9—C10—C11	−176.81 (17)
C6—Fe1—C4—C5	−48.5 (3)	Fe1—C9—C10—C11	−116.81 (17)
C10—Fe1—C4—C5	−82.20 (15)	C8—C9—C10—Fe1	−60.00 (13)
C3—Fe1—C4—C5	118.7 (2)	C7—C6—C10—C9	0.5 (2)
C2—Fe1—C4—C5	81.21 (14)	Fe1—C6—C10—C9	−59.14 (12)
C1—Fe1—C4—C5	37.49 (13)	C7—C6—C10—C11	176.06 (18)
C7—Fe1—C4—C5	160.6 (2)	Fe1—C6—C10—C11	116.4 (2)
C8—Fe1—C4—C5	−166.69 (13)	C7—C6—C10—Fe1	59.63 (13)
C9—Fe1—C4—C3	115.94 (15)	C6—Fe1—C10—C9	117.91 (15)
C6—Fe1—C4—C3	−167.2 (2)	C3—Fe1—C10—C9	−45.2 (2)
C10—Fe1—C4—C3	159.12 (13)	C2—Fe1—C10—C9	160.7 (2)
C2—Fe1—C4—C3	−37.47 (14)	C1—Fe1—C10—C9	−164.44 (12)
C1—Fe1—C4—C3	−81.20 (15)	C4—Fe1—C10—C9	−80.36 (14)
C5—Fe1—C4—C3	−118.7 (2)	C5—Fe1—C10—C9	−122.90 (13)
C7—Fe1—C4—C3	41.9 (3)	C7—Fe1—C10—C9	80.68 (12)
C8—Fe1—C4—C3	74.63 (17)	C8—Fe1—C10—C9	37.27 (12)
C3—C4—C5—C1	0.2 (2)	C9—Fe1—C10—C6	−117.91 (15)
Fe1—C4—C5—C1	−59.39 (15)	C3—Fe1—C10—C6	−163.1 (2)
C3—C4—C5—Fe1	59.57 (15)	C2—Fe1—C10—C6	42.8 (3)
C2—C1—C5—C4	0.0 (2)	C1—Fe1—C10—C6	77.64 (14)
Fe1—C1—C5—C4	59.44 (15)	C4—Fe1—C10—C6	161.73 (12)
C2—C1—C5—Fe1	−59.44 (15)	C5—Fe1—C10—C6	119.19 (12)
C9—Fe1—C5—C4	73.43 (16)	C7—Fe1—C10—C6	−37.23 (11)
C6—Fe1—C5—C4	160.41 (13)	C8—Fe1—C10—C6	−80.64 (12)
C10—Fe1—C5—C4	116.66 (14)	C9—Fe1—C10—C11	115.73 (19)
C3—Fe1—C5—C4	−38.14 (14)	C6—Fe1—C10—C11	−126.36 (19)
C2—Fe1—C5—C4	−81.87 (15)	C3—Fe1—C10—C11	70.5 (3)
C1—Fe1—C5—C4	−119.4 (2)	C2—Fe1—C10—C11	−83.6 (3)
C7—Fe1—C5—C4	−162.5 (2)	C1—Fe1—C10—C11	−48.71 (18)
C8—Fe1—C5—C4	36.5 (3)	C4—Fe1—C10—C11	35.37 (18)
C9—Fe1—C5—C1	−167.19 (13)	C5—Fe1—C10—C11	−7.17 (17)
C6—Fe1—C5—C1	−80.21 (16)	C7—Fe1—C10—C11	−163.58 (17)
C10—Fe1—C5—C1	−123.96 (14)	C8—Fe1—C10—C11	153.00 (16)
C3—Fe1—C5—C1	81.24 (15)	N2—N1—C11—C10	2.6 (3)
C2—Fe1—C5—C1	37.51 (14)	N2—N1—C11—C12	−176.20 (16)
C4—Fe1—C5—C1	119.4 (2)	C9—C10—C11—N1	−171.86 (19)
C7—Fe1—C5—C1	−43.2 (3)	C6—C10—C11—N1	13.2 (3)
C8—Fe1—C5—C1	155.9 (2)	Fe1—C10—C11—N1	103.5 (2)
C9—Fe1—C6—C7	−80.80 (12)	C9—C10—C11—C12	6.9 (3)
C10—Fe1—C6—C7	−119.61 (16)	C6—C10—C11—C12	−168.03 (18)
C3—Fe1—C6—C7	40.1 (3)	Fe1—C10—C11—C12	−77.7 (2)
C2—Fe1—C6—C7	74.84 (14)	N4—N3—C13—N2	1.5 (3)
C1—Fe1—C6—C7	117.07 (12)	N4—N3—C13—C14	−179.9 (2)
C4—Fe1—C6—C7	−165.2 (2)	C15—N2—C13—N3	−1.8 (2)
C5—Fe1—C6—C7	159.45 (12)	N1—N2—C13—N3	−171.75 (18)
C8—Fe1—C6—C7	−37.23 (12)	C15—N2—C13—C14	179.5 (2)
C9—Fe1—C6—C10	38.81 (11)	N1—N2—C13—C14	9.5 (3)
C3—Fe1—C6—C10	159.7 (2)	N3—N4—C15—N2	−0.6 (3)
C2—Fe1—C6—C10	−165.55 (11)	N3—N4—C15—C16	179.7 (2)
C1—Fe1—C6—C10	−123.32 (11)	C13—N2—C15—N4	1.5 (2)
C4—Fe1—C6—C10	−45.6 (3)	N1—N2—C15—N4	171.25 (18)
C5—Fe1—C6—C10	−80.93 (13)	C13—N2—C15—C16	−178.9 (2)
C7—Fe1—C6—C10	119.61 (16)	N1—N2—C15—C16	−9.1 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···Cg1	0.98	2.52	3.255 (3)	132
C5—H5···Cg3ⁱ	0.98	2.87	3.703 (5)	144

Symmetry code: (i) x, −y−1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	[Fe(C₅H₅)(C₁₁H₁₃N₄)]
M_r	322.19
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	8.7851 (18), 13.271 (3), 13.035 (3)
β (°)	104.49 (3)
V (Å³)	1471.4 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.02
Crystal size (mm)	0.30 × 0.26 × 0.20

Data collection
Diffractometer	Rigaku/MSC MODEL? CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.749, 0.822
No. of measured, independent and observed [I > 2σ(I)] reflections	14449, 2583, 2485
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.068, 1.09
No. of reflections	2583
No. of parameters	193
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.18

Computer programs: CrystalClear (Rigaku/MSC, 2006), 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
C6—H6···Cg1	0.98	2.519	3.255 (3)	131.7
C5—H5···Cg3ⁱ	0.98	2.868	3.703 (5)	143.7

Symmetry code: (i) x, −y−1/2, z−1/2.

Acknowledgements

This work was supported by the National Natural Science Foundation of China (No. 20572102), the Innovation Fund for Outstanding Scholar of Henan Province (No. 074200510005) and the Natural Science Foundation of Henan Province (No. 0524270054).

References

Hao, X. Q., Gong, J. F., Song, W. T., Wu, Y. J. & Song, M. P. (2007). Inorg. Chem. Commun. 10, 371–375. Web of Science CSD CrossRef CAS Google Scholar
Huo, S. Q., Wu, Y. J., Zhu, Y. & Yang, L. (1994). J. Organomet. Chem. 470, 17–22. CAS Google Scholar
Rigaku/MSC (2006). CrystalClear. Rigaku/MSC, The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wu, Y. J., Huo, S. Q., Gong, J. F., Cui, X. L., Ding, L., Ding, K. L., Du, C. X., Liu, Y. H. & Song, M. P. (2001). J. Organomet. Chem. 637–639, 27–46. Web of Science CrossRef CAS Google Scholar