N′-(4-Hy­droxy­benzyl­idene)ferrocene-1-carbohydrazide

Li, W.; Song, M.; Xu, Y.

doi:10.1107/S1600536811050835

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 1| January 2012| Page m8

doi:10.1107/S1600536811050835

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N′-(4-Hydroxybenzylidene)ferrocene-1-carbohydrazide

Wen-juan Li,^a Manman Song ^a and Yan Xu ^a ^*

^aDepartment of Chemistry, Zhengzhou University, Zhengzhou 450052, People's Republic of China
^*Correspondence e-mail: xuyan@zzu.edu.cn

(Received 30 October 2011; accepted 26 November 2011; online 3 December 2011)

In the title compound, [Fe(C₅H₅)₂(C₁₃H₁₁N₂O₂)], the dihedral angle between the benzene ring and the cyclopentadiene ring bonded to the carbonyl group is 26.1 (2)°. In the crystal, bifurcated O—H⋯(O,N) and N—H⋯O hydrogen bonds link the molecules into a three-dimensional network.

Related literature

For background to ferrocenylcarbonylhydrazone complexes and the synthesis of the title compound, see: Ma et al. (1988 ).

Experimental

Crystal data

[Fe(C₅H₅)₂(C₁₃H₁₁N₂O₂)]
M_r = 348.18
Orthorhombic, P 2₁ 2₁ 2₁
a = 11.341 (2) Å
b = 11.669 (2) Å
c = 11.748 (2) Å
V = 1554.7 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.98 mm⁻¹
T = 293 K
0.21 × 0.18 × 0.17 mm

Data collection

Rigaku Saturn diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2006 ) T_min = 0.821, T_max = 0.851
13023 measured reflections
3691 independent reflections
3139 reflections with I > 2σ(I)
R_int = 0.043

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.097
S = 1.06
3691 reflections
208 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.28 e Å⁻³
Absolute structure: Flack (1983 ), 1583 Friedel pairs
Flack parameter: 0.07 (2)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2B⋯O1ⁱ	0.86	2.20	3.035 (3)	163
O1—H1A⋯O2ⁱⁱ	0.82	2.03	2.838 (3)	170
O1—H1A⋯N1ⁱⁱ	0.82	2.59	3.028 (3)	115
Symmetry codes: (i) $[-x+{\script{1\over 2}}, -y+1, z+{\script{1\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ .

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: PLATON (Spek, 2009 ); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2006).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811050835/lh5370sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811050835/lh5370Isup2.hkl

checkCIF report

Comment top

It is known that ferrocenyl-bearing hydrazones can form stable complexes with various transition metal ions (Ma et al., 1988). To further explore these types of structures, we synthesized the title compound and its crystal structure is presented herein.

The molecular structure of the title compound is shown in Fig. 1. The distance between the two cyclopentadiene rings of the ferrocene is 3.2871 (4) Å. The distance between Fe1 and the mean-planes of the five-membered rings are 1.6377 (5) Å and 1.6498 (5) Å. The dihedral angle between the benzene ring and the cyclopentadiene ring bonded to the carbonyl group is 26.1 (2)°. In the crystal, bifurcated O—H···(O,N) and N—H···O hydrogen bonds link molecules into a three-dimensional network (Table 1).

Related literature top

For background to ferrocenylcarbonylhydrazone complexes and the synthesis of the title compound, see: Ma et al. (1988).

Experimental top

The synthesis of the title compound followed the procedure of Ma et al. (1988). The title compound (0.02 mmol) was dissolved in acetonitrile (3 mL) with a little methanol. Slow evaportation at room temperature for two weeks gave red crystals.

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: PLATON (Spek, 2009); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2006).

Figures top

Fig. 1. The molecular structure of the title compound with 30% displacement ellipsoids for non-H atoms.

N'-(4-Hydroxybenzylidene)ferrocene-1-carbohydrazide top

Crystal data top

[Fe(C₅H₅)₂(C₁₃H₁₁N₂O₂)]	F(000) = 720
M_r = 348.18	D_x = 1.488 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4569 reflections
a = 11.341 (2) Å	θ = 2.5–2.5°
b = 11.669 (2) Å	µ = 0.98 mm⁻¹
c = 11.748 (2) Å	T = 293 K
V = 1554.7 (5) Å³	Prism, red
Z = 4	0.21 × 0.18 × 0.17 mm

Data collection top

Rigaku Saturn diffractometer	3691 independent reflections
Radiation source: fine-focus sealed tube	3139 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.043
Detector resolution: 28.5714 pixels mm^-1	θ_max = 27.9°, θ_min = 2.5°
ω scans	h = −14→11
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2006)	k = −14→14
T_min = 0.821, T_max = 0.851	l = −15→15
13023 measured reflections

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)] = 0.047	H-atom parameters constrained
wR(F²) = 0.097	w = 1/[σ²(F_o²) + (0.0432P)²] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
3691 reflections	Δρ_max = 0.20 e Å⁻³
208 parameters	Δρ_min = −0.28 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1583 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.07 (2)

Crystal data top

[Fe(C₅H₅)₂(C₁₃H₁₁N₂O₂)]	V = 1554.7 (5) Å³
M_r = 348.18	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 11.341 (2) Å	µ = 0.98 mm⁻¹
b = 11.669 (2) Å	T = 293 K
c = 11.748 (2) Å	0.21 × 0.18 × 0.17 mm

Data collection top

Rigaku Saturn diffractometer	3691 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2006)	3139 reflections with I > 2σ(I)
T_min = 0.821, T_max = 0.851	R_int = 0.043
13023 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	H-atom parameters constrained
wR(F²) = 0.097	Δρ_max = 0.20 e Å⁻³
S = 1.06	Δρ_min = −0.28 e Å⁻³
3691 reflections	Absolute structure: Flack (1983), 1583 Friedel pairs
208 parameters	Absolute structure parameter: 0.07 (2)
0 restraints

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
C1	0.1100 (2)	0.3799 (2)	0.4653 (2)	0.0338 (6)
C2	0.2016 (3)	0.3023 (3)	0.4696 (3)	0.0515 (9)
H2A	0.2036	0.2415	0.4184	0.062*
C3	0.2907 (3)	0.3143 (3)	0.5494 (3)	0.0508 (9)
H3A	0.3513	0.2607	0.5521	0.061*
C4	0.2904 (2)	0.4054 (3)	0.6253 (2)	0.0384 (6)
C5	0.1976 (3)	0.4829 (3)	0.6188 (3)	0.0427 (8)
H5A	0.1956	0.5447	0.6688	0.051*
C6	0.1083 (3)	0.4706 (2)	0.5400 (3)	0.0424 (7)
H6A	0.0471	0.5236	0.5374	0.051*
C7	0.3819 (3)	0.4244 (2)	0.7082 (3)	0.0435 (7)
H7A	0.3778	0.4906	0.7521	0.052*
C8	0.6301 (3)	0.3160 (2)	0.8454 (2)	0.0374 (6)
C9	0.7054 (2)	0.3576 (3)	0.9383 (3)	0.0381 (7)
C10	0.7210 (3)	0.4729 (3)	0.9792 (3)	0.0479 (8)
H10A	0.6798	0.5412	0.9510	0.058*
C11	0.8062 (3)	0.4703 (3)	1.0672 (3)	0.0575 (9)
H11A	0.8350	0.5367	1.1100	0.069*
C12	0.8441 (3)	0.3547 (3)	1.0817 (3)	0.0573 (9)
H12A	0.9036	0.3277	1.1360	0.069*
C13	0.7833 (3)	0.2868 (3)	1.0025 (3)	0.0506 (8)
H13A	0.7932	0.2040	0.9925	0.061*
C14	0.9200 (4)	0.5014 (5)	0.7790 (5)	0.0972 (17)
H14A	0.8701	0.5578	0.7402	0.117*
C15	0.9991 (4)	0.5243 (5)	0.8663 (5)	0.0931 (16)
H15A	1.0128	0.5998	0.9004	0.112*
C16	1.0543 (3)	0.4238 (5)	0.8989 (4)	0.0871 (14)
H16A	1.1137	0.4158	0.9590	0.105*
C17	1.0091 (4)	0.3347 (5)	0.8301 (5)	0.0936 (16)
H17A	1.0320	0.2538	0.8331	0.112*
C18	0.9254 (4)	0.3842 (6)	0.7547 (4)	0.0965 (17)
H18A	0.8803	0.3437	0.6960	0.116*
Fe1	0.87527 (4)	0.40949 (4)	0.91860 (4)	0.04623 (14)
N1	0.4684 (2)	0.3563 (2)	0.7252 (2)	0.0396 (6)
N2	0.5467 (2)	0.3903 (2)	0.8087 (2)	0.0397 (6)
H2B	0.5425	0.4581	0.8371	0.048*
O1	0.02012 (17)	0.37099 (16)	0.38868 (17)	0.0424 (5)
H1A	0.0456	0.3451	0.3286	0.064*
O2	0.6370 (2)	0.21835 (16)	0.80566 (19)	0.0493 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0353 (15)	0.0315 (14)	0.0345 (13)	−0.0021 (12)	−0.0008 (12)	0.0008 (11)
C2	0.056 (2)	0.0384 (17)	0.060 (2)	0.0098 (15)	−0.0180 (18)	−0.0153 (15)
C3	0.0468 (18)	0.0448 (18)	0.061 (2)	0.0154 (15)	−0.0174 (17)	−0.0116 (16)
C4	0.0348 (15)	0.0375 (15)	0.0430 (15)	−0.0012 (14)	−0.0057 (12)	−0.0004 (14)
C5	0.0427 (18)	0.0408 (17)	0.0446 (18)	0.0070 (14)	−0.0067 (14)	−0.0138 (14)
C6	0.0361 (17)	0.0418 (16)	0.0491 (17)	0.0104 (14)	−0.0057 (14)	−0.0099 (14)
C7	0.0413 (16)	0.0415 (15)	0.0478 (16)	−0.0003 (16)	−0.0109 (16)	−0.0044 (13)
C8	0.0307 (14)	0.0428 (15)	0.0386 (15)	−0.0030 (15)	0.0011 (13)	0.0010 (12)
C9	0.0335 (14)	0.0421 (16)	0.0388 (16)	0.0027 (13)	−0.0023 (13)	0.0018 (13)
C10	0.0463 (19)	0.0475 (19)	0.0500 (19)	0.0101 (15)	−0.0107 (16)	−0.0091 (16)
C11	0.051 (2)	0.065 (2)	0.057 (2)	0.0126 (17)	−0.0208 (18)	−0.0205 (19)
C12	0.055 (2)	0.073 (2)	0.0444 (17)	0.0098 (18)	−0.0180 (17)	−0.0001 (18)
C13	0.0500 (18)	0.053 (2)	0.049 (2)	0.0102 (16)	−0.0089 (16)	0.0089 (16)
C14	0.069 (3)	0.142 (5)	0.081 (3)	−0.026 (3)	−0.006 (3)	0.041 (3)
C15	0.059 (3)	0.112 (4)	0.108 (4)	−0.031 (3)	0.000 (3)	0.007 (3)
C16	0.037 (2)	0.132 (4)	0.092 (3)	−0.004 (3)	−0.008 (2)	−0.009 (3)
C17	0.068 (3)	0.109 (4)	0.103 (4)	0.013 (3)	0.036 (3)	−0.020 (3)
C18	0.067 (3)	0.166 (5)	0.056 (3)	−0.047 (3)	0.011 (2)	−0.018 (3)
Fe1	0.0355 (2)	0.0557 (3)	0.0474 (2)	−0.0009 (2)	−0.0079 (2)	0.0001 (2)
N1	0.0354 (13)	0.0474 (14)	0.0358 (13)	−0.0021 (12)	−0.0047 (11)	−0.0023 (11)
N2	0.0385 (13)	0.0375 (13)	0.0432 (14)	0.0065 (11)	−0.0143 (11)	−0.0045 (11)
O1	0.0376 (11)	0.0454 (12)	0.0441 (12)	0.0019 (9)	−0.0083 (9)	−0.0090 (9)
O2	0.0495 (12)	0.0403 (11)	0.0582 (14)	0.0066 (11)	−0.0090 (12)	−0.0118 (10)

Geometric parameters (Å, º) top

C1—O1	1.364 (3)	C11—H11A	0.9800
C1—C2	1.379 (4)	C12—C13	1.403 (5)
C1—C6	1.375 (4)	C12—Fe1	2.051 (4)
C2—C3	1.385 (4)	C12—H12A	0.9800
C2—H2A	0.9300	C13—Fe1	2.027 (3)
C3—C4	1.388 (4)	C13—H13A	0.9800
C3—H3A	0.9300	C14—C18	1.399 (7)
C4—C5	1.390 (4)	C14—C15	1.389 (7)
C4—C7	1.440 (4)	C14—Fe1	2.025 (5)
C5—C6	1.379 (4)	C14—H14A	0.9800
C5—H5A	0.9300	C15—C16	1.384 (7)
C6—H6A	0.9300	C15—Fe1	2.036 (4)
C7—N1	1.279 (4)	C15—H15A	0.9800
C7—H7A	0.9300	C16—C17	1.413 (7)
C8—O2	1.233 (3)	C16—Fe1	2.050 (4)
C8—N2	1.354 (4)	C16—H16A	0.9800
C8—C9	1.469 (4)	C17—C18	1.420 (7)
C9—C13	1.425 (4)	C17—Fe1	2.037 (4)
C9—C10	1.440 (4)	C17—H17A	0.9800
C9—Fe1	2.032 (3)	C18—Fe1	2.029 (4)
C10—C11	1.416 (4)	C18—H18A	0.9800
C10—Fe1	2.029 (3)	N1—N2	1.381 (3)
C10—H10A	0.9800	N2—H2B	0.8600
C11—C12	1.426 (5)	O1—H1A	0.8200
C11—Fe1	2.041 (4)

O1—C1—C2	122.4 (2)	C15—C16—Fe1	69.7 (2)
O1—C1—C6	118.0 (2)	C17—C16—Fe1	69.2 (2)
C2—C1—C6	119.5 (3)	C15—C16—H16A	126.2
C1—C2—C3	120.5 (3)	C17—C16—H16A	126.2
C1—C2—H2A	119.8	Fe1—C16—H16A	126.2
C3—C2—H2A	119.8	C16—C17—C18	107.5 (5)
C4—C3—C2	120.7 (3)	C16—C17—Fe1	70.3 (2)
C4—C3—H3A	119.6	C18—C17—Fe1	69.3 (3)
C2—C3—H3A	119.6	C16—C17—H17A	126.3
C3—C4—C5	117.7 (3)	C18—C17—H17A	126.3
C3—C4—C7	123.4 (3)	Fe1—C17—H17A	126.3
C5—C4—C7	118.8 (3)	C17—C18—C14	107.5 (4)
C6—C5—C4	121.7 (3)	C17—C18—Fe1	69.8 (3)
C6—C5—H5A	119.2	C14—C18—Fe1	69.6 (3)
C4—C5—H5A	119.2	C17—C18—H18A	126.3
C1—C6—C5	119.9 (3)	C14—C18—H18A	126.3
C1—C6—H6A	120.1	Fe1—C18—H18A	126.3
C5—C6—H6A	120.1	C14—Fe1—C13	153.77 (19)
N1—C7—C4	124.3 (3)	C14—Fe1—C9	119.18 (17)
N1—C7—H7A	117.9	C13—Fe1—C9	41.10 (12)
C4—C7—H7A	117.9	C14—Fe1—C10	107.86 (19)
O2—C8—N2	121.1 (3)	C13—Fe1—C10	69.11 (13)
O2—C8—C9	123.3 (3)	C9—Fe1—C10	41.53 (12)
N2—C8—C9	115.5 (2)	C14—Fe1—C11	127.2 (2)
C13—C9—C10	106.8 (3)	C13—Fe1—C11	68.42 (15)
C13—C9—C8	124.2 (3)	C9—Fe1—C11	69.04 (13)
C10—C9—C8	128.9 (3)	C10—Fe1—C11	40.71 (12)
C13—C9—Fe1	69.24 (18)	C14—Fe1—C18	40.4 (2)
C10—C9—Fe1	69.11 (18)	C13—Fe1—C18	120.18 (19)
C8—C9—Fe1	124.4 (2)	C9—Fe1—C18	109.30 (15)
C9—C10—C11	107.9 (3)	C10—Fe1—C18	128.87 (19)
C9—C10—Fe1	69.36 (17)	C11—Fe1—C18	165.9 (2)
C11—C10—Fe1	70.1 (2)	C14—Fe1—C17	68.1 (2)
C9—C10—H10A	126.1	C13—Fe1—C17	109.22 (18)
C11—C10—H10A	126.1	C9—Fe1—C17	129.56 (19)
Fe1—C10—H10A	126.1	C10—Fe1—C17	168.0 (2)
C12—C11—C10	108.3 (3)	C11—Fe1—C17	150.7 (2)
C12—C11—Fe1	70.0 (2)	C18—Fe1—C17	40.9 (2)
C10—C11—Fe1	69.2 (2)	C14—Fe1—C16	67.5 (2)
C12—C11—H11A	125.8	C13—Fe1—C16	128.46 (18)
C10—C11—H11A	125.8	C9—Fe1—C16	167.32 (19)
Fe1—C11—H11A	125.8	C10—Fe1—C16	149.77 (18)
C13—C12—C11	107.8 (3)	C11—Fe1—C16	116.65 (17)
C13—C12—Fe1	68.9 (2)	C18—Fe1—C16	68.10 (18)
C11—C12—Fe1	69.2 (2)	C17—Fe1—C16	40.46 (19)
C13—C12—H12A	126.1	C14—Fe1—C15	40.01 (19)
C11—C12—H12A	126.1	C13—Fe1—C15	165.12 (19)
Fe1—C12—H12A	126.1	C9—Fe1—C15	152.17 (19)
C12—C13—C9	109.2 (3)	C10—Fe1—C15	117.4 (2)
C12—C13—Fe1	70.8 (2)	C11—Fe1—C15	107.1 (2)
C9—C13—Fe1	69.66 (18)	C18—Fe1—C15	67.4 (2)
C12—C13—H13A	125.4	C17—Fe1—C15	67.3 (2)
C9—C13—H13A	125.4	C16—Fe1—C15	39.6 (2)
Fe1—C13—H13A	125.4	C14—Fe1—C12	164.9 (2)
C18—C14—C15	108.0 (5)	C13—Fe1—C12	40.26 (13)
C18—C14—Fe1	70.0 (3)	C9—Fe1—C12	68.74 (13)
C15—C14—Fe1	70.4 (3)	C10—Fe1—C12	68.75 (13)
C18—C14—H14A	126.0	C11—Fe1—C12	40.80 (14)
C15—C14—H14A	126.0	C18—Fe1—C12	152.8 (2)
Fe1—C14—H14A	126.0	C17—Fe1—C12	118.2 (2)
C16—C15—C14	109.5 (5)	C16—Fe1—C12	107.55 (17)
C16—C15—Fe1	70.8 (3)	C15—Fe1—C12	127.30 (19)
C14—C15—Fe1	69.5 (3)	C7—N1—N2	115.2 (2)
C16—C15—H15A	125.2	C8—N2—N1	119.4 (2)
C14—C15—H15A	125.2	C8—N2—H2B	120.3
Fe1—C15—H15A	125.2	N1—N2—H2B	120.3
C15—C16—C17	107.5 (4)	C1—O1—H1A	109.5

O1—C1—C2—C3	−179.6 (3)	C11—C10—Fe1—C9	119.0 (3)
C6—C1—C2—C3	1.0 (5)	C9—C10—Fe1—C11	−119.0 (3)
C1—C2—C3—C4	−1.0 (6)	C9—C10—Fe1—C18	74.3 (3)
C2—C3—C4—C5	0.5 (5)	C11—C10—Fe1—C18	−166.7 (3)
C2—C3—C4—C7	−178.2 (3)	C9—C10—Fe1—C17	46.0 (10)
C3—C4—C5—C6	0.1 (5)	C11—C10—Fe1—C17	165.0 (9)
C7—C4—C5—C6	178.8 (3)	C9—C10—Fe1—C16	−170.1 (3)
O1—C1—C6—C5	−179.9 (3)	C11—C10—Fe1—C16	−51.1 (4)
C2—C1—C6—C5	−0.4 (5)	C9—C10—Fe1—C15	156.4 (2)
C4—C5—C6—C1	−0.1 (5)	C11—C10—Fe1—C15	−84.6 (3)
C3—C4—C7—N1	−4.5 (5)	C9—C10—Fe1—C12	−81.5 (2)
C5—C4—C7—N1	176.8 (3)	C11—C10—Fe1—C12	37.5 (2)
O2—C8—C9—C13	−8.5 (5)	C12—C11—Fe1—C14	−167.3 (2)
N2—C8—C9—C13	168.2 (3)	C10—C11—Fe1—C14	73.0 (3)
O2—C8—C9—C10	168.3 (3)	C12—C11—Fe1—C13	37.09 (19)
N2—C8—C9—C10	−15.0 (5)	C10—C11—Fe1—C13	−82.6 (2)
O2—C8—C9—Fe1	78.4 (3)	C12—C11—Fe1—C9	81.3 (2)
N2—C8—C9—Fe1	−104.9 (3)	C10—C11—Fe1—C9	−38.39 (19)
C13—C9—C10—C11	−0.6 (4)	C12—C11—Fe1—C10	119.7 (3)
C8—C9—C10—C11	−177.8 (3)	C12—C11—Fe1—C18	167.2 (6)
Fe1—C9—C10—C11	−59.8 (2)	C10—C11—Fe1—C18	47.5 (7)
C13—C9—C10—Fe1	59.2 (2)	C12—C11—Fe1—C17	−54.0 (4)
C8—C9—C10—Fe1	−118.0 (3)	C10—C11—Fe1—C17	−173.7 (4)
C9—C10—C11—C12	0.1 (4)	C12—C11—Fe1—C16	−86.3 (3)
Fe1—C10—C11—C12	−59.2 (3)	C10—C11—Fe1—C16	154.0 (2)
C9—C10—C11—Fe1	59.3 (2)	C12—C11—Fe1—C15	−127.9 (2)
C10—C11—C12—C13	0.5 (4)	C10—C11—Fe1—C15	112.4 (3)
Fe1—C11—C12—C13	−58.3 (3)	C10—C11—Fe1—C12	−119.7 (3)
C10—C11—C12—Fe1	58.8 (3)	C17—C18—Fe1—C14	118.5 (4)
C11—C12—C13—C9	−0.8 (4)	C17—C18—Fe1—C13	−84.8 (3)
Fe1—C12—C13—C9	−59.3 (2)	C14—C18—Fe1—C13	156.6 (3)
C11—C12—C13—Fe1	58.4 (3)	C17—C18—Fe1—C9	−128.8 (3)
C10—C9—C13—C12	0.9 (4)	C14—C18—Fe1—C9	112.7 (3)
C8—C9—C13—C12	178.2 (3)	C17—C18—Fe1—C10	−171.4 (3)
Fe1—C9—C13—C12	60.0 (3)	C14—C18—Fe1—C10	70.1 (3)
C10—C9—C13—Fe1	−59.1 (2)	C17—C18—Fe1—C11	150.5 (6)
C8—C9—C13—Fe1	118.2 (3)	C14—C18—Fe1—C11	32.0 (8)
C18—C14—C15—C16	−0.5 (6)	C14—C18—Fe1—C17	−118.5 (4)
Fe1—C14—C15—C16	59.7 (4)	C17—C18—Fe1—C16	38.0 (3)
C18—C14—C15—Fe1	−60.2 (3)	C14—C18—Fe1—C16	−80.6 (3)
C14—C15—C16—C17	0.2 (6)	C17—C18—Fe1—C15	80.9 (3)
Fe1—C15—C16—C17	59.1 (3)	C14—C18—Fe1—C15	−37.7 (3)
C14—C15—C16—Fe1	−58.9 (3)	C17—C18—Fe1—C12	−48.0 (5)
C15—C16—C17—C18	0.2 (5)	C14—C18—Fe1—C12	−166.5 (3)
Fe1—C16—C17—C18	59.6 (3)	C16—C17—Fe1—C14	80.6 (3)
C15—C16—C17—Fe1	−59.4 (3)	C18—C17—Fe1—C14	−37.8 (3)
C16—C17—C18—C14	−0.5 (5)	C16—C17—Fe1—C13	−127.3 (3)
Fe1—C17—C18—C14	59.7 (3)	C18—C17—Fe1—C13	114.3 (3)
C16—C17—C18—Fe1	−60.2 (3)	C16—C17—Fe1—C9	−169.0 (3)
C15—C14—C18—C17	0.6 (5)	C18—C17—Fe1—C9	72.6 (4)
Fe1—C14—C18—C17	−59.8 (3)	C16—C17—Fe1—C10	152.8 (8)
C15—C14—C18—Fe1	60.4 (3)	C18—C17—Fe1—C10	34.4 (11)
C18—C14—Fe1—C13	−50.9 (5)	C16—C17—Fe1—C11	−47.4 (5)
C15—C14—Fe1—C13	−169.5 (4)	C18—C17—Fe1—C11	−165.8 (4)
C18—C14—Fe1—C9	−85.8 (3)	C16—C17—Fe1—C18	118.4 (5)
C15—C14—Fe1—C9	155.5 (3)	C18—C17—Fe1—C16	−118.4 (5)
C18—C14—Fe1—C10	−129.7 (3)	C16—C17—Fe1—C15	37.2 (3)
C15—C14—Fe1—C10	111.7 (3)	C18—C17—Fe1—C15	−81.2 (3)
C18—C14—Fe1—C11	−170.7 (3)	C16—C17—Fe1—C12	−84.2 (3)
C15—C14—Fe1—C11	70.7 (4)	C18—C17—Fe1—C12	157.4 (3)
C15—C14—Fe1—C18	−118.6 (5)	C15—C16—Fe1—C14	36.8 (3)
C18—C14—Fe1—C17	38.3 (3)	C17—C16—Fe1—C14	−82.1 (4)
C15—C14—Fe1—C17	−80.3 (4)	C15—C16—Fe1—C13	−167.5 (3)
C18—C14—Fe1—C16	82.2 (3)	C17—C16—Fe1—C13	73.5 (4)
C15—C14—Fe1—C16	−36.5 (3)	C15—C16—Fe1—C9	161.2 (7)
C18—C14—Fe1—C15	118.6 (5)	C17—C16—Fe1—C9	42.2 (9)
C18—C14—Fe1—C12	155.8 (6)	C15—C16—Fe1—C10	−50.2 (5)
C15—C14—Fe1—C12	37.2 (8)	C17—C16—Fe1—C10	−169.2 (3)
C12—C13—Fe1—C14	−169.6 (4)	C15—C16—Fe1—C11	−84.8 (3)
C9—C13—Fe1—C14	−49.6 (5)	C17—C16—Fe1—C11	156.2 (3)
C12—C13—Fe1—C9	−120.0 (3)	C15—C16—Fe1—C18	80.6 (4)
C12—C13—Fe1—C10	−81.4 (2)	C17—C16—Fe1—C18	−38.3 (3)
C9—C13—Fe1—C10	38.61 (18)	C15—C16—Fe1—C17	118.9 (5)
C12—C13—Fe1—C11	−37.58 (19)	C17—C16—Fe1—C15	−118.9 (5)
C9—C13—Fe1—C11	82.4 (2)	C15—C16—Fe1—C12	−128.0 (3)
C12—C13—Fe1—C18	154.9 (3)	C17—C16—Fe1—C12	113.1 (3)
C9—C13—Fe1—C18	−85.1 (3)	C16—C15—Fe1—C14	−120.5 (5)
C12—C13—Fe1—C17	111.2 (3)	C16—C15—Fe1—C13	41.2 (9)
C9—C13—Fe1—C17	−128.8 (2)	C14—C15—Fe1—C13	161.7 (6)
C12—C13—Fe1—C16	70.0 (3)	C16—C15—Fe1—C9	−171.3 (3)
C9—C13—Fe1—C16	−170.0 (2)	C14—C15—Fe1—C9	−50.8 (6)
C12—C13—Fe1—C15	37.6 (8)	C16—C15—Fe1—C10	154.2 (3)
C9—C13—Fe1—C15	157.6 (7)	C14—C15—Fe1—C10	−85.4 (4)
C9—C13—Fe1—C12	120.0 (3)	C16—C15—Fe1—C11	111.4 (3)
C13—C9—Fe1—C14	157.3 (3)	C14—C15—Fe1—C11	−128.1 (3)
C10—C9—Fe1—C14	−84.2 (3)	C16—C15—Fe1—C18	−82.5 (3)
C8—C9—Fe1—C14	39.3 (3)	C14—C15—Fe1—C18	38.0 (3)
C10—C9—Fe1—C13	118.4 (3)	C16—C15—Fe1—C17	−38.0 (3)
C8—C9—Fe1—C13	−118.0 (3)	C14—C15—Fe1—C17	82.5 (4)
C13—C9—Fe1—C10	−118.4 (3)	C14—C15—Fe1—C16	120.5 (5)
C8—C9—Fe1—C10	123.6 (3)	C16—C15—Fe1—C12	70.9 (4)
C13—C9—Fe1—C11	−80.8 (2)	C14—C15—Fe1—C12	−168.6 (3)
C10—C9—Fe1—C11	37.65 (19)	C13—C12—Fe1—C14	162.1 (6)
C8—C9—Fe1—C11	161.2 (3)	C11—C12—Fe1—C14	42.3 (7)
C13—C9—Fe1—C18	114.1 (3)	C11—C12—Fe1—C13	−119.8 (3)
C10—C9—Fe1—C18	−127.4 (3)	C13—C12—Fe1—C9	37.65 (18)
C8—C9—Fe1—C18	−3.8 (3)	C11—C12—Fe1—C9	−82.1 (2)
C13—C9—Fe1—C17	72.7 (3)	C13—C12—Fe1—C10	82.4 (2)
C10—C9—Fe1—C17	−168.9 (3)	C11—C12—Fe1—C10	−37.42 (19)
C8—C9—Fe1—C17	−45.3 (4)	C13—C12—Fe1—C11	119.8 (3)
C13—C9—Fe1—C16	38.3 (8)	C13—C12—Fe1—C18	−53.4 (4)
C10—C9—Fe1—C16	156.7 (7)	C11—C12—Fe1—C18	−173.2 (3)
C8—C9—Fe1—C16	−79.7 (8)	C13—C12—Fe1—C17	−86.9 (3)
C13—C9—Fe1—C15	−167.9 (4)	C11—C12—Fe1—C17	153.3 (2)
C10—C9—Fe1—C15	−49.4 (4)	C13—C12—Fe1—C16	−129.5 (2)
C8—C9—Fe1—C15	74.1 (5)	C11—C12—Fe1—C16	110.7 (3)
C13—C9—Fe1—C12	−36.9 (2)	C13—C12—Fe1—C15	−168.7 (3)
C10—C9—Fe1—C12	81.5 (2)	C11—C12—Fe1—C15	71.6 (3)
C8—C9—Fe1—C12	−154.9 (3)	C4—C7—N1—N2	−180.0 (3)
C9—C10—Fe1—C14	114.1 (2)	O2—C8—N2—N1	−0.2 (4)
C11—C10—Fe1—C14	−126.9 (3)	C9—C8—N2—N1	−177.0 (2)
C9—C10—Fe1—C13	−38.22 (18)	C7—N1—N2—C8	169.6 (3)
C11—C10—Fe1—C13	80.8 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···O1ⁱ	0.86	2.20	3.035 (3)	163
O1—H1A···O2ⁱⁱ	0.82	2.03	2.838 (3)	170
O1—H1A···N1ⁱⁱ	0.82	2.59	3.028 (3)	115

Symmetry codes: (i) −x+1/2, −y+1, z+1/2; (ii) x−1/2, −y+1/2, −z+1.

Experimental details

Crystal data
Chemical formula	[Fe(C₅H₅)₂(C₁₃H₁₁N₂O₂)]
M_r	348.18
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	293
a, b, c (Å)	11.341 (2), 11.669 (2), 11.748 (2)
V (Å³)	1554.7 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.98
Crystal size (mm)	0.21 × 0.18 × 0.17

Data collection
Diffractometer	Rigaku Saturn diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2006)
T_min, T_max	0.821, 0.851
No. of measured, independent and observed [I > 2σ(I)] reflections	13023, 3691, 3139
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.097, 1.06
No. of reflections	3691
No. of parameters	208
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.28
Absolute structure	Flack (1983), 1583 Friedel pairs
Absolute structure parameter	0.07 (2)

Computer programs: CrystalClear (Rigaku/MSC, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009), CrystalStructure (Rigaku/MSC, 2006).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···O1ⁱ	0.86	2.20	3.035 (3)	163.3
O1—H1A···O2ⁱⁱ	0.82	2.03	2.838 (3)	169.7
O1—H1A···N1ⁱⁱ	0.82	2.59	3.028 (3)	115.2

Symmetry codes: (i) −x+1/2, −y+1, z+1/2; (ii) x−1/2, −y+1/2, −z+1.

Acknowledgements

We gratefully acknowledge financial support by the National Natural Science Foundation of China (No. 21171149).

References

Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Ma, Y.-X., Li, F., Sun, H.-S. & Xie, J. (1988). Inorg. Chim. Acta, 149, 209–212. CAS Google Scholar
Rigaku/MSC (2006). CrystalClear and CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar