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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536811050835/lh5370sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536811050835/lh5370Isup2.hkl
Contains datablock I

CCDC reference: 747781

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.047
  • wR factor = 0.097
  • Data-to-parameter ratio = 17.7

checkCIF/PLATON results

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Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for N2 -- C8 .. 5.5 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C14 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C15 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C17 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C18 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for Fe1 PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.600 2 PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L= 0.600 5 PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF .... 1
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.90 From the CIF: _reflns_number_total 3691 Count of symmetry unique reflns 2126 Completeness (_total/calc) 173.61% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1565 Fraction of Friedel pairs measured 0.736 Are heavy atom types Z>Si present yes PLAT005_ALERT_5_G No _iucr_refine_instructions_details in CIF .... ? PLAT153_ALERT_1_G The su's on the Cell Axes are Equal .......... 0.00200 Ang. PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature 293 K PLAT917_ALERT_2_G The FCF is likely NOT based on a BASF/TWIN Flack !
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 9 ALERT level C = Check. Ensure it is not caused by an omission or oversight 6 ALERT level G = General information/check it is not something unexpected 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 7 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check

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.

Refinement top

All H atoms were placed in calculated positions, with C—H = 0.93-0.98 Å, N—H = 0.86Å, O—H = 0.82Å and included in the refinement in a riding-model approximation with Uiso = 1.2Ueq(C,N) or 1.5Ueq(O).

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
[Figure 1] 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
Mr = 348.18Dx = 1.488 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 4569 reflections
a = 11.341 (2) Åθ = 2.5–2.5°
b = 11.669 (2) ŵ = 0.98 mm1
c = 11.748 (2) ÅT = 293 K
V = 1554.7 (5) Å3Prism, red
Z = 40.21 × 0.18 × 0.17 mm
Data collection top
Rigaku Saturn
diffractometer
3691 independent reflections
Radiation source: fine-focus sealed tube3139 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.043
Detector resolution: 28.5714 pixels mm-1θmax = 27.9°, θmin = 2.5°
ω scansh = 1411
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2006)
k = 1414
Tmin = 0.821, Tmax = 0.851l = 1515
13023 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.047H-atom parameters constrained
wR(F2) = 0.097 w = 1/[σ2(Fo2) + (0.0432P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max < 0.001
3691 reflectionsΔρmax = 0.20 e Å3
208 parametersΔρmin = 0.28 e Å3
0 restraintsAbsolute structure: Flack (1983), 1583 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.07 (2)
Crystal data top
[Fe(C5H5)2(C13H11N2O2)]V = 1554.7 (5) Å3
Mr = 348.18Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 11.341 (2) ŵ = 0.98 mm1
b = 11.669 (2) ÅT = 293 K
c = 11.748 (2) Å0.21 × 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)
Tmin = 0.821, Tmax = 0.851Rint = 0.043
13023 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.047H-atom parameters constrained
wR(F2) = 0.097Δρmax = 0.20 e Å3
S = 1.06Δρmin = 0.28 e Å3
3691 reflectionsAbsolute structure: Flack (1983), 1583 Friedel pairs
208 parametersAbsolute 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
xyzUiso*/Ueq
C10.1100 (2)0.3799 (2)0.4653 (2)0.0338 (6)
C20.2016 (3)0.3023 (3)0.4696 (3)0.0515 (9)
H2A0.20360.24150.41840.062*
C30.2907 (3)0.3143 (3)0.5494 (3)0.0508 (9)
H3A0.35130.26070.55210.061*
C40.2904 (2)0.4054 (3)0.6253 (2)0.0384 (6)
C50.1976 (3)0.4829 (3)0.6188 (3)0.0427 (8)
H5A0.19560.54470.66880.051*
C60.1083 (3)0.4706 (2)0.5400 (3)0.0424 (7)
H6A0.04710.52360.53740.051*
C70.3819 (3)0.4244 (2)0.7082 (3)0.0435 (7)
H7A0.37780.49060.75210.052*
C80.6301 (3)0.3160 (2)0.8454 (2)0.0374 (6)
C90.7054 (2)0.3576 (3)0.9383 (3)0.0381 (7)
C100.7210 (3)0.4729 (3)0.9792 (3)0.0479 (8)
H10A0.67980.54120.95100.058*
C110.8062 (3)0.4703 (3)1.0672 (3)0.0575 (9)
H11A0.83500.53671.11000.069*
C120.8441 (3)0.3547 (3)1.0817 (3)0.0573 (9)
H12A0.90360.32771.13600.069*
C130.7833 (3)0.2868 (3)1.0025 (3)0.0506 (8)
H13A0.79320.20400.99250.061*
C140.9200 (4)0.5014 (5)0.7790 (5)0.0972 (17)
H14A0.87010.55780.74020.117*
C150.9991 (4)0.5243 (5)0.8663 (5)0.0931 (16)
H15A1.01280.59980.90040.112*
C161.0543 (3)0.4238 (5)0.8989 (4)0.0871 (14)
H16A1.11370.41580.95900.105*
C171.0091 (4)0.3347 (5)0.8301 (5)0.0936 (16)
H17A1.03200.25380.83310.112*
C180.9254 (4)0.3842 (6)0.7547 (4)0.0965 (17)
H18A0.88030.34370.69600.116*
Fe10.87527 (4)0.40949 (4)0.91860 (4)0.04623 (14)
N10.4684 (2)0.3563 (2)0.7252 (2)0.0396 (6)
N20.5467 (2)0.3903 (2)0.8087 (2)0.0397 (6)
H2B0.54250.45810.83710.048*
O10.02012 (17)0.37099 (16)0.38868 (17)0.0424 (5)
H1A0.04560.34510.32860.064*
O20.6370 (2)0.21835 (16)0.80566 (19)0.0493 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0353 (15)0.0315 (14)0.0345 (13)0.0021 (12)0.0008 (12)0.0008 (11)
C20.056 (2)0.0384 (17)0.060 (2)0.0098 (15)0.0180 (18)0.0153 (15)
C30.0468 (18)0.0448 (18)0.061 (2)0.0154 (15)0.0174 (17)0.0116 (16)
C40.0348 (15)0.0375 (15)0.0430 (15)0.0012 (14)0.0057 (12)0.0004 (14)
C50.0427 (18)0.0408 (17)0.0446 (18)0.0070 (14)0.0067 (14)0.0138 (14)
C60.0361 (17)0.0418 (16)0.0491 (17)0.0104 (14)0.0057 (14)0.0099 (14)
C70.0413 (16)0.0415 (15)0.0478 (16)0.0003 (16)0.0109 (16)0.0044 (13)
C80.0307 (14)0.0428 (15)0.0386 (15)0.0030 (15)0.0011 (13)0.0010 (12)
C90.0335 (14)0.0421 (16)0.0388 (16)0.0027 (13)0.0023 (13)0.0018 (13)
C100.0463 (19)0.0475 (19)0.0500 (19)0.0101 (15)0.0107 (16)0.0091 (16)
C110.051 (2)0.065 (2)0.057 (2)0.0126 (17)0.0208 (18)0.0205 (19)
C120.055 (2)0.073 (2)0.0444 (17)0.0098 (18)0.0180 (17)0.0001 (18)
C130.0500 (18)0.053 (2)0.049 (2)0.0102 (16)0.0089 (16)0.0089 (16)
C140.069 (3)0.142 (5)0.081 (3)0.026 (3)0.006 (3)0.041 (3)
C150.059 (3)0.112 (4)0.108 (4)0.031 (3)0.000 (3)0.007 (3)
C160.037 (2)0.132 (4)0.092 (3)0.004 (3)0.008 (2)0.009 (3)
C170.068 (3)0.109 (4)0.103 (4)0.013 (3)0.036 (3)0.020 (3)
C180.067 (3)0.166 (5)0.056 (3)0.047 (3)0.011 (2)0.018 (3)
Fe10.0355 (2)0.0557 (3)0.0474 (2)0.0009 (2)0.0079 (2)0.0001 (2)
N10.0354 (13)0.0474 (14)0.0358 (13)0.0021 (12)0.0047 (11)0.0023 (11)
N20.0385 (13)0.0375 (13)0.0432 (14)0.0065 (11)0.0143 (11)0.0045 (11)
O10.0376 (11)0.0454 (12)0.0441 (12)0.0019 (9)0.0083 (9)0.0090 (9)
O20.0495 (12)0.0403 (11)0.0582 (14)0.0066 (11)0.0090 (12)0.0118 (10)
Geometric parameters (Å, º) top
C1—O11.364 (3)C11—H11A0.9800
C1—C21.379 (4)C12—C131.403 (5)
C1—C61.375 (4)C12—Fe12.051 (4)
C2—C31.385 (4)C12—H12A0.9800
C2—H2A0.9300C13—Fe12.027 (3)
C3—C41.388 (4)C13—H13A0.9800
C3—H3A0.9300C14—C181.399 (7)
C4—C51.390 (4)C14—C151.389 (7)
C4—C71.440 (4)C14—Fe12.025 (5)
C5—C61.379 (4)C14—H14A0.9800
C5—H5A0.9300C15—C161.384 (7)
C6—H6A0.9300C15—Fe12.036 (4)
C7—N11.279 (4)C15—H15A0.9800
C7—H7A0.9300C16—C171.413 (7)
C8—O21.233 (3)C16—Fe12.050 (4)
C8—N21.354 (4)C16—H16A0.9800
C8—C91.469 (4)C17—C181.420 (7)
C9—C131.425 (4)C17—Fe12.037 (4)
C9—C101.440 (4)C17—H17A0.9800
C9—Fe12.032 (3)C18—Fe12.029 (4)
C10—C111.416 (4)C18—H18A0.9800
C10—Fe12.029 (3)N1—N21.381 (3)
C10—H10A0.9800N2—H2B0.8600
C11—C121.426 (5)O1—H1A0.8200
C11—Fe12.041 (4)
O1—C1—C2122.4 (2)C15—C16—Fe169.7 (2)
O1—C1—C6118.0 (2)C17—C16—Fe169.2 (2)
C2—C1—C6119.5 (3)C15—C16—H16A126.2
C1—C2—C3120.5 (3)C17—C16—H16A126.2
C1—C2—H2A119.8Fe1—C16—H16A126.2
C3—C2—H2A119.8C16—C17—C18107.5 (5)
C4—C3—C2120.7 (3)C16—C17—Fe170.3 (2)
C4—C3—H3A119.6C18—C17—Fe169.3 (3)
C2—C3—H3A119.6C16—C17—H17A126.3
C3—C4—C5117.7 (3)C18—C17—H17A126.3
C3—C4—C7123.4 (3)Fe1—C17—H17A126.3
C5—C4—C7118.8 (3)C17—C18—C14107.5 (4)
C6—C5—C4121.7 (3)C17—C18—Fe169.8 (3)
C6—C5—H5A119.2C14—C18—Fe169.6 (3)
C4—C5—H5A119.2C17—C18—H18A126.3
C1—C6—C5119.9 (3)C14—C18—H18A126.3
C1—C6—H6A120.1Fe1—C18—H18A126.3
C5—C6—H6A120.1C14—Fe1—C13153.77 (19)
N1—C7—C4124.3 (3)C14—Fe1—C9119.18 (17)
N1—C7—H7A117.9C13—Fe1—C941.10 (12)
C4—C7—H7A117.9C14—Fe1—C10107.86 (19)
O2—C8—N2121.1 (3)C13—Fe1—C1069.11 (13)
O2—C8—C9123.3 (3)C9—Fe1—C1041.53 (12)
N2—C8—C9115.5 (2)C14—Fe1—C11127.2 (2)
C13—C9—C10106.8 (3)C13—Fe1—C1168.42 (15)
C13—C9—C8124.2 (3)C9—Fe1—C1169.04 (13)
C10—C9—C8128.9 (3)C10—Fe1—C1140.71 (12)
C13—C9—Fe169.24 (18)C14—Fe1—C1840.4 (2)
C10—C9—Fe169.11 (18)C13—Fe1—C18120.18 (19)
C8—C9—Fe1124.4 (2)C9—Fe1—C18109.30 (15)
C9—C10—C11107.9 (3)C10—Fe1—C18128.87 (19)
C9—C10—Fe169.36 (17)C11—Fe1—C18165.9 (2)
C11—C10—Fe170.1 (2)C14—Fe1—C1768.1 (2)
C9—C10—H10A126.1C13—Fe1—C17109.22 (18)
C11—C10—H10A126.1C9—Fe1—C17129.56 (19)
Fe1—C10—H10A126.1C10—Fe1—C17168.0 (2)
C12—C11—C10108.3 (3)C11—Fe1—C17150.7 (2)
C12—C11—Fe170.0 (2)C18—Fe1—C1740.9 (2)
C10—C11—Fe169.2 (2)C14—Fe1—C1667.5 (2)
C12—C11—H11A125.8C13—Fe1—C16128.46 (18)
C10—C11—H11A125.8C9—Fe1—C16167.32 (19)
Fe1—C11—H11A125.8C10—Fe1—C16149.77 (18)
C13—C12—C11107.8 (3)C11—Fe1—C16116.65 (17)
C13—C12—Fe168.9 (2)C18—Fe1—C1668.10 (18)
C11—C12—Fe169.2 (2)C17—Fe1—C1640.46 (19)
C13—C12—H12A126.1C14—Fe1—C1540.01 (19)
C11—C12—H12A126.1C13—Fe1—C15165.12 (19)
Fe1—C12—H12A126.1C9—Fe1—C15152.17 (19)
C12—C13—C9109.2 (3)C10—Fe1—C15117.4 (2)
C12—C13—Fe170.8 (2)C11—Fe1—C15107.1 (2)
C9—C13—Fe169.66 (18)C18—Fe1—C1567.4 (2)
C12—C13—H13A125.4C17—Fe1—C1567.3 (2)
C9—C13—H13A125.4C16—Fe1—C1539.6 (2)
Fe1—C13—H13A125.4C14—Fe1—C12164.9 (2)
C18—C14—C15108.0 (5)C13—Fe1—C1240.26 (13)
C18—C14—Fe170.0 (3)C9—Fe1—C1268.74 (13)
C15—C14—Fe170.4 (3)C10—Fe1—C1268.75 (13)
C18—C14—H14A126.0C11—Fe1—C1240.80 (14)
C15—C14—H14A126.0C18—Fe1—C12152.8 (2)
Fe1—C14—H14A126.0C17—Fe1—C12118.2 (2)
C16—C15—C14109.5 (5)C16—Fe1—C12107.55 (17)
C16—C15—Fe170.8 (3)C15—Fe1—C12127.30 (19)
C14—C15—Fe169.5 (3)C7—N1—N2115.2 (2)
C16—C15—H15A125.2C8—N2—N1119.4 (2)
C14—C15—H15A125.2C8—N2—H2B120.3
Fe1—C15—H15A125.2N1—N2—H2B120.3
C15—C16—C17107.5 (4)C1—O1—H1A109.5
O1—C1—C2—C3179.6 (3)C11—C10—Fe1—C9119.0 (3)
C6—C1—C2—C31.0 (5)C9—C10—Fe1—C11119.0 (3)
C1—C2—C3—C41.0 (6)C9—C10—Fe1—C1874.3 (3)
C2—C3—C4—C50.5 (5)C11—C10—Fe1—C18166.7 (3)
C2—C3—C4—C7178.2 (3)C9—C10—Fe1—C1746.0 (10)
C3—C4—C5—C60.1 (5)C11—C10—Fe1—C17165.0 (9)
C7—C4—C5—C6178.8 (3)C9—C10—Fe1—C16170.1 (3)
O1—C1—C6—C5179.9 (3)C11—C10—Fe1—C1651.1 (4)
C2—C1—C6—C50.4 (5)C9—C10—Fe1—C15156.4 (2)
C4—C5—C6—C10.1 (5)C11—C10—Fe1—C1584.6 (3)
C3—C4—C7—N14.5 (5)C9—C10—Fe1—C1281.5 (2)
C5—C4—C7—N1176.8 (3)C11—C10—Fe1—C1237.5 (2)
O2—C8—C9—C138.5 (5)C12—C11—Fe1—C14167.3 (2)
N2—C8—C9—C13168.2 (3)C10—C11—Fe1—C1473.0 (3)
O2—C8—C9—C10168.3 (3)C12—C11—Fe1—C1337.09 (19)
N2—C8—C9—C1015.0 (5)C10—C11—Fe1—C1382.6 (2)
O2—C8—C9—Fe178.4 (3)C12—C11—Fe1—C981.3 (2)
N2—C8—C9—Fe1104.9 (3)C10—C11—Fe1—C938.39 (19)
C13—C9—C10—C110.6 (4)C12—C11—Fe1—C10119.7 (3)
C8—C9—C10—C11177.8 (3)C12—C11—Fe1—C18167.2 (6)
Fe1—C9—C10—C1159.8 (2)C10—C11—Fe1—C1847.5 (7)
C13—C9—C10—Fe159.2 (2)C12—C11—Fe1—C1754.0 (4)
C8—C9—C10—Fe1118.0 (3)C10—C11—Fe1—C17173.7 (4)
C9—C10—C11—C120.1 (4)C12—C11—Fe1—C1686.3 (3)
Fe1—C10—C11—C1259.2 (3)C10—C11—Fe1—C16154.0 (2)
C9—C10—C11—Fe159.3 (2)C12—C11—Fe1—C15127.9 (2)
C10—C11—C12—C130.5 (4)C10—C11—Fe1—C15112.4 (3)
Fe1—C11—C12—C1358.3 (3)C10—C11—Fe1—C12119.7 (3)
C10—C11—C12—Fe158.8 (3)C17—C18—Fe1—C14118.5 (4)
C11—C12—C13—C90.8 (4)C17—C18—Fe1—C1384.8 (3)
Fe1—C12—C13—C959.3 (2)C14—C18—Fe1—C13156.6 (3)
C11—C12—C13—Fe158.4 (3)C17—C18—Fe1—C9128.8 (3)
C10—C9—C13—C120.9 (4)C14—C18—Fe1—C9112.7 (3)
C8—C9—C13—C12178.2 (3)C17—C18—Fe1—C10171.4 (3)
Fe1—C9—C13—C1260.0 (3)C14—C18—Fe1—C1070.1 (3)
C10—C9—C13—Fe159.1 (2)C17—C18—Fe1—C11150.5 (6)
C8—C9—C13—Fe1118.2 (3)C14—C18—Fe1—C1132.0 (8)
C18—C14—C15—C160.5 (6)C14—C18—Fe1—C17118.5 (4)
Fe1—C14—C15—C1659.7 (4)C17—C18—Fe1—C1638.0 (3)
C18—C14—C15—Fe160.2 (3)C14—C18—Fe1—C1680.6 (3)
C14—C15—C16—C170.2 (6)C17—C18—Fe1—C1580.9 (3)
Fe1—C15—C16—C1759.1 (3)C14—C18—Fe1—C1537.7 (3)
C14—C15—C16—Fe158.9 (3)C17—C18—Fe1—C1248.0 (5)
C15—C16—C17—C180.2 (5)C14—C18—Fe1—C12166.5 (3)
Fe1—C16—C17—C1859.6 (3)C16—C17—Fe1—C1480.6 (3)
C15—C16—C17—Fe159.4 (3)C18—C17—Fe1—C1437.8 (3)
C16—C17—C18—C140.5 (5)C16—C17—Fe1—C13127.3 (3)
Fe1—C17—C18—C1459.7 (3)C18—C17—Fe1—C13114.3 (3)
C16—C17—C18—Fe160.2 (3)C16—C17—Fe1—C9169.0 (3)
C15—C14—C18—C170.6 (5)C18—C17—Fe1—C972.6 (4)
Fe1—C14—C18—C1759.8 (3)C16—C17—Fe1—C10152.8 (8)
C15—C14—C18—Fe160.4 (3)C18—C17—Fe1—C1034.4 (11)
C18—C14—Fe1—C1350.9 (5)C16—C17—Fe1—C1147.4 (5)
C15—C14—Fe1—C13169.5 (4)C18—C17—Fe1—C11165.8 (4)
C18—C14—Fe1—C985.8 (3)C16—C17—Fe1—C18118.4 (5)
C15—C14—Fe1—C9155.5 (3)C18—C17—Fe1—C16118.4 (5)
C18—C14—Fe1—C10129.7 (3)C16—C17—Fe1—C1537.2 (3)
C15—C14—Fe1—C10111.7 (3)C18—C17—Fe1—C1581.2 (3)
C18—C14—Fe1—C11170.7 (3)C16—C17—Fe1—C1284.2 (3)
C15—C14—Fe1—C1170.7 (4)C18—C17—Fe1—C12157.4 (3)
C15—C14—Fe1—C18118.6 (5)C15—C16—Fe1—C1436.8 (3)
C18—C14—Fe1—C1738.3 (3)C17—C16—Fe1—C1482.1 (4)
C15—C14—Fe1—C1780.3 (4)C15—C16—Fe1—C13167.5 (3)
C18—C14—Fe1—C1682.2 (3)C17—C16—Fe1—C1373.5 (4)
C15—C14—Fe1—C1636.5 (3)C15—C16—Fe1—C9161.2 (7)
C18—C14—Fe1—C15118.6 (5)C17—C16—Fe1—C942.2 (9)
C18—C14—Fe1—C12155.8 (6)C15—C16—Fe1—C1050.2 (5)
C15—C14—Fe1—C1237.2 (8)C17—C16—Fe1—C10169.2 (3)
C12—C13—Fe1—C14169.6 (4)C15—C16—Fe1—C1184.8 (3)
C9—C13—Fe1—C1449.6 (5)C17—C16—Fe1—C11156.2 (3)
C12—C13—Fe1—C9120.0 (3)C15—C16—Fe1—C1880.6 (4)
C12—C13—Fe1—C1081.4 (2)C17—C16—Fe1—C1838.3 (3)
C9—C13—Fe1—C1038.61 (18)C15—C16—Fe1—C17118.9 (5)
C12—C13—Fe1—C1137.58 (19)C17—C16—Fe1—C15118.9 (5)
C9—C13—Fe1—C1182.4 (2)C15—C16—Fe1—C12128.0 (3)
C12—C13—Fe1—C18154.9 (3)C17—C16—Fe1—C12113.1 (3)
C9—C13—Fe1—C1885.1 (3)C16—C15—Fe1—C14120.5 (5)
C12—C13—Fe1—C17111.2 (3)C16—C15—Fe1—C1341.2 (9)
C9—C13—Fe1—C17128.8 (2)C14—C15—Fe1—C13161.7 (6)
C12—C13—Fe1—C1670.0 (3)C16—C15—Fe1—C9171.3 (3)
C9—C13—Fe1—C16170.0 (2)C14—C15—Fe1—C950.8 (6)
C12—C13—Fe1—C1537.6 (8)C16—C15—Fe1—C10154.2 (3)
C9—C13—Fe1—C15157.6 (7)C14—C15—Fe1—C1085.4 (4)
C9—C13—Fe1—C12120.0 (3)C16—C15—Fe1—C11111.4 (3)
C13—C9—Fe1—C14157.3 (3)C14—C15—Fe1—C11128.1 (3)
C10—C9—Fe1—C1484.2 (3)C16—C15—Fe1—C1882.5 (3)
C8—C9—Fe1—C1439.3 (3)C14—C15—Fe1—C1838.0 (3)
C10—C9—Fe1—C13118.4 (3)C16—C15—Fe1—C1738.0 (3)
C8—C9—Fe1—C13118.0 (3)C14—C15—Fe1—C1782.5 (4)
C13—C9—Fe1—C10118.4 (3)C14—C15—Fe1—C16120.5 (5)
C8—C9—Fe1—C10123.6 (3)C16—C15—Fe1—C1270.9 (4)
C13—C9—Fe1—C1180.8 (2)C14—C15—Fe1—C12168.6 (3)
C10—C9—Fe1—C1137.65 (19)C13—C12—Fe1—C14162.1 (6)
C8—C9—Fe1—C11161.2 (3)C11—C12—Fe1—C1442.3 (7)
C13—C9—Fe1—C18114.1 (3)C11—C12—Fe1—C13119.8 (3)
C10—C9—Fe1—C18127.4 (3)C13—C12—Fe1—C937.65 (18)
C8—C9—Fe1—C183.8 (3)C11—C12—Fe1—C982.1 (2)
C13—C9—Fe1—C1772.7 (3)C13—C12—Fe1—C1082.4 (2)
C10—C9—Fe1—C17168.9 (3)C11—C12—Fe1—C1037.42 (19)
C8—C9—Fe1—C1745.3 (4)C13—C12—Fe1—C11119.8 (3)
C13—C9—Fe1—C1638.3 (8)C13—C12—Fe1—C1853.4 (4)
C10—C9—Fe1—C16156.7 (7)C11—C12—Fe1—C18173.2 (3)
C8—C9—Fe1—C1679.7 (8)C13—C12—Fe1—C1786.9 (3)
C13—C9—Fe1—C15167.9 (4)C11—C12—Fe1—C17153.3 (2)
C10—C9—Fe1—C1549.4 (4)C13—C12—Fe1—C16129.5 (2)
C8—C9—Fe1—C1574.1 (5)C11—C12—Fe1—C16110.7 (3)
C13—C9—Fe1—C1236.9 (2)C13—C12—Fe1—C15168.7 (3)
C10—C9—Fe1—C1281.5 (2)C11—C12—Fe1—C1571.6 (3)
C8—C9—Fe1—C12154.9 (3)C4—C7—N1—N2180.0 (3)
C9—C10—Fe1—C14114.1 (2)O2—C8—N2—N10.2 (4)
C11—C10—Fe1—C14126.9 (3)C9—C8—N2—N1177.0 (2)
C9—C10—Fe1—C1338.22 (18)C7—N1—N2—C8169.6 (3)
C11—C10—Fe1—C1380.8 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2B···O1i0.862.203.035 (3)163
O1—H1A···O2ii0.822.032.838 (3)170
O1—H1A···N1ii0.822.593.028 (3)115
Symmetry codes: (i) x+1/2, y+1, z+1/2; (ii) x1/2, y+1/2, z+1.

Experimental details

Crystal data
Chemical formula[Fe(C5H5)2(C13H11N2O2)]
Mr348.18
Crystal system, space groupOrthorhombic, P212121
Temperature (K)293
a, b, c (Å)11.341 (2), 11.669 (2), 11.748 (2)
V3)1554.7 (5)
Z4
Radiation typeMo Kα
µ (mm1)0.98
Crystal size (mm)0.21 × 0.18 × 0.17
Data collection
DiffractometerRigaku Saturn
diffractometer
Absorption correctionMulti-scan
(CrystalClear; Rigaku/MSC, 2006)
Tmin, Tmax0.821, 0.851
No. of measured, independent and
observed [I > 2σ(I)] reflections
13023, 3691, 3139
Rint0.043
(sin θ/λ)max1)0.658
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.097, 1.06
No. of reflections3691
No. of parameters208
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.20, 0.28
Absolute structureFlack (1983), 1583 Friedel pairs
Absolute structure parameter0.07 (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···AD—HH···AD···AD—H···A
N2—H2B···O1i0.862.203.035 (3)163.3
O1—H1A···O2ii0.822.032.838 (3)169.7
O1—H1A···N1ii0.822.593.028 (3)115.2
Symmetry codes: (i) x+1/2, y+1, z+1/2; (ii) x1/2, y+1/2, z+1.
 

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