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The title compound, [Fe(C5H5)(C10H13N2O2], has been synthesized by the reaction of acetyl­ferrocene and hydrazine ethyl carbazate. Mol­ecules of the title compound form centrosymmetric R22(8) dimers via inter­molecular N—H...O=C hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805030242/br6218sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805030242/br6218Isup2.hkl
Contains datablock I

CCDC reference: 287457

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.008 Å
  • R factor = 0.060
  • wR factor = 0.184
  • Data-to-parameter ratio = 15.8

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.94 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.30 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for Fe PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 8
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 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 0 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

The title compound, (I), has been synthesized as part of our ongoing investigation of the chemistry of ferrocenyl derivatives (Shi et al., 2004; Shi, 2004). Although dithiocarbazate derivatives have been widely studied, the corresponding ferrocenyl carbazates have scarcely been explored. In order to exploit the chemistry of ferrocenyl carbazates, the crystal structure of (I) has been determined (Fig. 1).

Compound (I) crystallizes in the keto form and exists as the conformer in which the N1—N2 bond adopts a trans geometry with respect to CO, while the ethyl group adopts a cis geometry. The ferrocenyl and ethyl groups are cis to each other across the N1—N2 and CO bonds. Moreover, both cyclopentadienyl rings in the ferrocenyl group are in the eclipsed conformation. The bond lengths and angles of the CN—N(H)—C moiety are comparable with those of two dithiocarbazate compounds, Ar—C(CH3) N—N(H)—C(SCH2Ph)S [Ar = 2-furyl, (II) (Khoo et al., 2005); Ar = 2-thiophenyl, (III) (Chan et al., 2003)] (Table 1). The CN—N(H) plane between the aromatic ring and the ester group makes dihedral angles of 26.2 (3) and 5.1 (7)°, whereas the corresponding values are 2.90 (16) and 1.8 (2)° for (II), and 5.39 (13) and 11.37 (16)° for (III).

As in (II) and (III), paired intermolecular N—H···OC hydrogen bonds lead to the formation of centrosymmetric R22(8) dimers (Bernstein et al., 1995; Table 2; Fig. 2).

Experimental top

The title compound was synthesized by refluxing a solution of acetylferrocene and hydrazine ethyl carbazate (1:1) in ethanol for 4 h (yield, 82%). Orange single crystals of (I), suitable for X-ray analysis, were obtained by slow evaporation from a CH2Cl2–petroleum ether (Ratio?) solution (m.p. 452.6–454.1 K). IR (KBr, ν, cm−1): 3448.35 (br, m, NH), 1668 (s, CO), 1599 (vs, CN).

Refinement top

All H atoms were placed in geometrically idealized positions and subsequently treated as riding atoms, with C—H = 0.93–0.98 Å and N—H = 0.86 Å, and with Uiso(H) = 1.2Ueq(C,N) and 1.5Ueq(Cmethyl).

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. A projection, along the b axis, of part of the packing diagram for (I). Dashed lines indicate hydrogen bonds.
Ethyl N-[1-ferrocenylethylidene]hydrazine carbazate top
Crystal data top
[Fe(C5H5)(C10H13N2O2]F(000) = 1312
Mr = 314.16Dx = 1.454 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 36.770 (7) ÅCell parameters from 25 reflections
b = 7.6040 (15) Åθ = 10–13°
c = 10.366 (2) ŵ = 1.05 mm1
β = 97.82 (3)°T = 295 K
V = 2871.4 (10) Å3Block, orange
Z = 80.40 × 0.20 × 0.20 mm
Data collection top
Enraf–Nonius CAD4
diffractometer
2178 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.039
Graphite monochromatorθmax = 26.0°, θmin = 1.1°
ω/2θ scansh = 045
Absorption correction: empirical (using intensity measurements)
via ψ scan (North et al., 1968)
k = 09
Tmin = 0.747, Tmax = 0.803l = 1212
2848 measured reflections3 standard reflections every 200 reflections
2804 independent reflections intensity decay: none
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.060Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.184H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.098P)2 + 11.3526P]
where P = (Fo2 + 2Fc2)/3
2804 reflections(Δ/σ)max < 0.001
177 parametersΔρmax = 1.46 e Å3
13 restraintsΔρmin = 0.76 e Å3
Crystal data top
[Fe(C5H5)(C10H13N2O2]V = 2871.4 (10) Å3
Mr = 314.16Z = 8
Monoclinic, C2/cMo Kα radiation
a = 36.770 (7) ŵ = 1.05 mm1
b = 7.6040 (15) ÅT = 295 K
c = 10.366 (2) Å0.40 × 0.20 × 0.20 mm
β = 97.82 (3)°
Data collection top
Enraf–Nonius CAD4
diffractometer
2178 reflections with I > 2σ(I)
Absorption correction: empirical (using intensity measurements)
via ψ scan (North et al., 1968)
Rint = 0.039
Tmin = 0.747, Tmax = 0.8033 standard reflections every 200 reflections
2848 measured reflections intensity decay: none
2804 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.06013 restraints
wR(F2) = 0.184H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.098P)2 + 11.3526P]
where P = (Fo2 + 2Fc2)/3
2804 reflectionsΔρmax = 1.46 e Å3
177 parametersΔρmin = 0.76 e Å3
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
Fe0.071355 (18)0.23531 (8)0.20163 (6)0.0358 (3)
O10.18707 (10)0.3121 (6)0.7058 (3)0.0544 (9)
O20.24378 (11)0.3154 (8)0.6509 (4)0.0729 (13)
N10.19646 (11)0.2243 (6)0.5067 (4)0.0469 (10)
H1N0.21050.20630.44820.056*
N20.15917 (10)0.1892 (6)0.4785 (3)0.0405 (9)
C10.1754 (2)0.3384 (13)0.9268 (9)0.110
H1A0.15580.42150.90770.165*
H1B0.18690.35431.01490.165*
H1C0.16590.22110.91610.165*
C20.20340 (19)0.3672 (11)0.8349 (6)0.0778 (19)
H2A0.21020.49050.83400.093*
H2B0.22530.29900.86290.093*
C30.21109 (14)0.2866 (7)0.6248 (5)0.0476 (12)
C40.17159 (14)0.1219 (9)0.2542 (5)0.0546 (14)
H4A0.18040.23530.23210.082*
H4B0.15750.07060.17880.082*
H4C0.19210.04700.28380.082*
C50.14785 (12)0.1416 (6)0.3605 (4)0.0376 (10)
C60.10856 (12)0.1051 (6)0.3318 (4)0.0374 (10)
C70.08003 (13)0.1737 (7)0.3953 (4)0.0414 (10)
H70.08310.25260.46450.050*
C80.04652 (15)0.1046 (7)0.3379 (5)0.0494 (12)
H80.02360.13000.36160.059*
C90.05362 (15)0.0114 (7)0.2368 (5)0.0500 (12)
H90.03610.07580.18310.060*
C100.09188 (14)0.0121 (6)0.2319 (4)0.0438 (11)
H100.10400.07660.17460.053*
C110.06881 (18)0.5011 (8)0.1821 (5)0.0608 (15)
H110.07090.58180.25010.073*
C120.03581 (18)0.4243 (8)0.1213 (5)0.0619 (16)
H120.01240.44520.14190.074*
C130.04501 (18)0.3111 (8)0.0245 (5)0.0601 (15)
H130.02860.24340.03080.072*
C140.08348 (18)0.3164 (8)0.0246 (5)0.0588 (14)
H140.09670.25310.03020.071*
C150.09806 (17)0.4338 (8)0.1217 (6)0.0608 (15)
H150.12270.46260.14290.073*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe0.0478 (4)0.0327 (4)0.0242 (4)0.0027 (3)0.0050 (3)0.0026 (2)
O10.059 (2)0.075 (3)0.0299 (16)0.0061 (19)0.0060 (15)0.0094 (17)
O20.050 (2)0.126 (4)0.040 (2)0.013 (2)0.0021 (17)0.021 (2)
N10.042 (2)0.070 (3)0.0276 (19)0.001 (2)0.0020 (16)0.0054 (18)
N20.042 (2)0.052 (2)0.0255 (18)0.0018 (18)0.0045 (15)0.0002 (17)
C10.1100.1100.1100.0000.0150.000
C20.086 (4)0.103 (4)0.044 (3)0.023 (3)0.009 (3)0.020 (3)
C30.046 (3)0.059 (3)0.035 (2)0.001 (2)0.004 (2)0.001 (2)
C40.053 (3)0.077 (4)0.032 (2)0.003 (3)0.001 (2)0.008 (3)
C50.046 (2)0.038 (2)0.026 (2)0.005 (2)0.0030 (18)0.0010 (18)
C60.046 (2)0.036 (2)0.028 (2)0.0014 (19)0.0042 (18)0.0034 (17)
C70.053 (3)0.043 (3)0.025 (2)0.000 (2)0.0025 (19)0.0043 (19)
C80.050 (3)0.056 (3)0.042 (3)0.000 (2)0.004 (2)0.011 (2)
C90.058 (3)0.041 (3)0.046 (3)0.012 (2)0.010 (2)0.004 (2)
C100.061 (3)0.032 (2)0.035 (2)0.001 (2)0.006 (2)0.0015 (18)
C110.095 (4)0.041 (2)0.043 (2)0.005 (3)0.003 (3)0.006 (2)
C120.074 (4)0.059 (3)0.051 (3)0.029 (3)0.004 (3)0.022 (3)
C130.076 (4)0.061 (3)0.037 (3)0.010 (3)0.015 (3)0.011 (2)
C140.083 (4)0.059 (3)0.036 (3)0.005 (3)0.011 (3)0.012 (2)
C150.067 (3)0.054 (3)0.056 (3)0.014 (3)0.011 (3)0.026 (3)
Geometric parameters (Å, º) top
Fe—C112.032 (6)C4—H4A0.9600
Fe—C92.036 (5)C4—H4B0.9600
Fe—C102.036 (5)C4—H4C0.9600
Fe—C152.037 (5)C5—C61.461 (6)
Fe—C132.039 (5)C6—C71.412 (7)
Fe—C122.042 (5)C6—C101.438 (6)
Fe—C62.042 (4)C7—C81.396 (7)
Fe—C82.042 (5)C7—H70.9300
Fe—C142.042 (5)C8—C91.421 (8)
Fe—C72.044 (4)C8—H80.9300
O1—C21.453 (6)C9—C101.415 (7)
O1—C31.313 (6)C9—H90.9300
O2—C31.216 (6)C10—H100.9300
N1—N21.388 (5)C11—C151.412 (9)
N1—C31.353 (6)C11—C121.415 (9)
N1—H1N0.8600C11—H110.9300
N2—C51.290 (6)C12—C131.398 (9)
C1—C21.509 (8)C12—H120.9300
C1—H1A0.9600C13—C141.415 (8)
C1—H1B0.9600C13—H130.9300
C1—H1C0.9600C14—C151.397 (9)
C2—H2A0.9700C14—H140.9300
C2—H2B0.9700C15—H150.9300
C4—C51.503 (7)
C11—Fe—C9157.4 (2)H4A—C4—H4B109.5
C11—Fe—C10161.0 (2)C5—C4—H4C109.5
C9—Fe—C1040.7 (2)H4A—C4—H4C109.5
C11—Fe—C1540.6 (2)H4B—C4—H4C109.5
C9—Fe—C15160.0 (3)N2—C5—C4125.4 (4)
C10—Fe—C15123.9 (2)N2—C5—C6115.4 (4)
C11—Fe—C1367.6 (2)C4—C5—C6119.2 (4)
C9—Fe—C13107.3 (2)C7—C6—C10107.1 (4)
C10—Fe—C13121.4 (2)C7—C6—C5127.7 (4)
C15—Fe—C1367.7 (2)C10—C6—C5125.3 (4)
C11—Fe—C1240.7 (2)C7—C6—Fe69.8 (2)
C9—Fe—C12121.2 (2)C10—C6—Fe69.1 (3)
C10—Fe—C12156.4 (2)C5—C6—Fe126.7 (3)
C15—Fe—C1268.3 (3)C8—C7—C6109.3 (4)
C13—Fe—C1240.1 (2)C8—C7—Fe69.9 (3)
C11—Fe—C6124.4 (2)C6—C7—Fe69.7 (2)
C9—Fe—C668.71 (19)C8—C7—H7125.3
C10—Fe—C641.31 (18)C6—C7—H7125.3
C15—Fe—C6108.1 (2)Fe—C7—H7126.6
C13—Fe—C6157.7 (2)C7—C8—C9107.9 (5)
C12—Fe—C6160.9 (2)C7—C8—Fe70.1 (3)
C11—Fe—C8122.3 (2)C9—C8—Fe69.4 (3)
C9—Fe—C840.8 (2)C7—C8—H8126.0
C10—Fe—C868.6 (2)C9—C8—H8126.0
C15—Fe—C8158.1 (2)Fe—C8—H8126.1
C13—Fe—C8123.9 (2)C10—C9—C8108.2 (4)
C12—Fe—C8107.6 (2)C10—C9—Fe69.7 (3)
C6—Fe—C868.2 (2)C8—C9—Fe69.8 (3)
C11—Fe—C1467.9 (2)C10—C9—H9125.9
C9—Fe—C14123.6 (2)C8—C9—H9125.9
C10—Fe—C14107.2 (2)Fe—C9—H9126.2
C15—Fe—C1440.1 (2)C9—C10—C6107.5 (4)
C13—Fe—C1440.6 (2)C9—C10—Fe69.7 (3)
C12—Fe—C1468.1 (2)C6—C10—Fe69.6 (3)
C6—Fe—C14122.1 (2)C9—C10—H10126.2
C8—Fe—C14160.3 (2)C6—C10—H10126.2
C11—Fe—C7108.9 (2)Fe—C10—H10126.1
C9—Fe—C767.9 (2)C15—C11—C12108.1 (5)
C10—Fe—C768.38 (19)C15—C11—Fe69.9 (3)
C15—Fe—C7123.3 (2)C12—C11—Fe70.1 (3)
C13—Fe—C7160.2 (2)C15—C11—H11125.9
C12—Fe—C7124.6 (2)C12—C11—H11125.9
C6—Fe—C740.44 (19)Fe—C11—H11125.7
C8—Fe—C740.0 (2)C13—C12—C11107.3 (6)
C14—Fe—C7158.1 (2)C13—C12—Fe69.8 (3)
C2—O1—C3113.7 (4)C11—C12—Fe69.3 (3)
C3—N1—N2121.1 (4)C13—C12—H12126.3
C3—N1—H1N119.4C11—C12—H12126.3
N2—N1—H1N119.4Fe—C12—H12126.1
C5—N2—N1115.8 (4)C12—C13—C14108.8 (6)
C2—C1—H1A109.5C12—C13—Fe70.1 (3)
C2—C1—H1B109.5C14—C13—Fe69.8 (3)
H1A—C1—H1B109.5C12—C13—H13125.6
C2—C1—H1C109.5C14—C13—H13125.6
H1A—C1—H1C109.5Fe—C13—H13126.0
H1B—C1—H1C109.5C15—C14—C13107.7 (6)
O1—C2—C1107.9 (6)C15—C14—Fe69.8 (3)
O1—C2—H2A110.1C13—C14—Fe69.6 (3)
C1—C2—H2A110.1C15—C14—H14126.2
O1—C2—H2B110.1C13—C14—H14126.2
C1—C2—H2B110.1Fe—C14—H14126.1
H2A—C2—H2B108.4C14—C15—C11108.1 (5)
O1—C3—O2124.2 (5)C14—C15—Fe70.2 (3)
O1—C3—N1114.3 (4)C11—C15—Fe69.5 (3)
O2—C3—N1121.6 (5)C14—C15—H15126.0
C5—C4—H4A109.5C11—C15—H15126.0
C5—C4—H4B109.5Fe—C15—H15126.0
C3—N1—N2—C5175.5 (5)C12—Fe—C10—C947.4 (7)
C3—O1—C2—C1163.0 (6)C6—Fe—C10—C9118.7 (4)
C2—O1—C3—O24.1 (9)C8—Fe—C10—C937.7 (3)
C2—O1—C3—N1176.0 (5)C14—Fe—C10—C9121.9 (3)
N2—N1—C3—O2179.0 (5)C7—Fe—C10—C980.8 (3)
N2—N1—C3—O11.1 (7)C11—Fe—C10—C647.6 (7)
N1—N2—C5—C6180.0 (4)C9—Fe—C10—C6118.7 (4)
N1—N2—C5—C40.1 (7)C15—Fe—C10—C678.6 (3)
N2—C5—C6—C725.7 (7)C13—Fe—C10—C6161.4 (3)
C4—C5—C6—C7154.3 (5)C12—Fe—C10—C6166.1 (5)
N2—C5—C6—C10153.5 (5)C8—Fe—C10—C681.0 (3)
C4—C5—C6—C1026.5 (7)C14—Fe—C10—C6119.4 (3)
N2—C5—C6—Fe117.6 (4)C7—Fe—C10—C637.9 (3)
C4—C5—C6—Fe62.5 (6)C9—Fe—C11—C15162.6 (5)
C11—Fe—C6—C778.6 (4)C10—Fe—C11—C1541.1 (8)
C9—Fe—C6—C780.5 (3)C13—Fe—C11—C1581.4 (4)
C10—Fe—C6—C7118.3 (4)C12—Fe—C11—C15119.1 (5)
C15—Fe—C6—C7120.5 (3)C6—Fe—C11—C1577.3 (4)
C13—Fe—C6—C7164.2 (6)C8—Fe—C11—C15161.6 (3)
C12—Fe—C6—C744.6 (8)C14—Fe—C11—C1537.4 (3)
C8—Fe—C6—C736.5 (3)C7—Fe—C11—C15119.5 (3)
C14—Fe—C6—C7162.3 (3)C9—Fe—C11—C1243.6 (7)
C11—Fe—C6—C10163.1 (3)C10—Fe—C11—C12160.1 (6)
C9—Fe—C6—C1037.8 (3)C15—Fe—C11—C12119.1 (5)
C15—Fe—C6—C10121.2 (3)C13—Fe—C11—C1237.7 (4)
C13—Fe—C6—C1045.8 (7)C6—Fe—C11—C12163.7 (3)
C12—Fe—C6—C10162.9 (7)C8—Fe—C11—C1279.3 (4)
C8—Fe—C6—C1081.8 (3)C14—Fe—C11—C1281.7 (4)
C14—Fe—C6—C1079.3 (4)C7—Fe—C11—C12121.4 (3)
C7—Fe—C6—C10118.3 (4)C15—C11—C12—C130.0 (6)
C11—Fe—C6—C544.0 (5)Fe—C11—C12—C1359.8 (4)
C9—Fe—C6—C5156.9 (5)C15—C11—C12—Fe59.7 (4)
C10—Fe—C6—C5119.1 (5)C11—Fe—C12—C13118.5 (5)
C15—Fe—C6—C52.1 (5)C9—Fe—C12—C1379.5 (4)
C13—Fe—C6—C573.3 (8)C10—Fe—C12—C1345.4 (8)
C12—Fe—C6—C578.0 (8)C15—Fe—C12—C1380.7 (4)
C8—Fe—C6—C5159.1 (5)C6—Fe—C12—C13163.5 (6)
C14—Fe—C6—C539.7 (5)C8—Fe—C12—C13122.1 (4)
C7—Fe—C6—C5122.6 (5)C14—Fe—C12—C1337.5 (4)
C10—C6—C7—C80.5 (5)C7—Fe—C12—C13162.9 (4)
C5—C6—C7—C8179.8 (4)C9—Fe—C12—C11161.9 (3)
Fe—C6—C7—C858.9 (3)C10—Fe—C12—C11164.0 (5)
C10—C6—C7—Fe59.3 (3)C15—Fe—C12—C1137.8 (3)
C5—C6—C7—Fe121.3 (5)C13—Fe—C12—C11118.5 (5)
C11—Fe—C7—C8118.0 (4)C6—Fe—C12—C1145.0 (8)
C9—Fe—C7—C838.0 (3)C8—Fe—C12—C11119.4 (4)
C10—Fe—C7—C882.0 (3)C14—Fe—C12—C1181.1 (4)
C15—Fe—C7—C8160.7 (3)C7—Fe—C12—C1178.6 (4)
C13—Fe—C7—C841.6 (8)C11—C12—C13—C140.1 (6)
C12—Fe—C7—C875.6 (4)Fe—C12—C13—C1459.3 (4)
C6—Fe—C7—C8120.7 (4)C11—C12—C13—Fe59.4 (4)
C14—Fe—C7—C8164.4 (6)C11—Fe—C13—C1238.2 (4)
C11—Fe—C7—C6121.3 (3)C9—Fe—C13—C12118.3 (4)
C9—Fe—C7—C682.7 (3)C10—Fe—C13—C12160.5 (4)
C10—Fe—C7—C638.7 (3)C15—Fe—C13—C1282.3 (4)
C15—Fe—C7—C678.6 (4)C6—Fe—C13—C12165.8 (5)
C13—Fe—C7—C6162.2 (6)C8—Fe—C13—C1276.6 (5)
C12—Fe—C7—C6163.8 (3)C14—Fe—C13—C12119.8 (6)
C8—Fe—C7—C6120.7 (4)C7—Fe—C13—C1245.7 (9)
C14—Fe—C7—C643.7 (7)C11—Fe—C13—C1481.6 (4)
C6—C7—C8—C90.5 (6)C9—Fe—C13—C14121.9 (4)
Fe—C7—C8—C959.3 (3)C10—Fe—C13—C1479.7 (4)
C6—C7—C8—Fe58.7 (3)C15—Fe—C13—C1437.5 (4)
C11—Fe—C8—C781.0 (4)C12—Fe—C13—C14119.8 (6)
C9—Fe—C8—C7119.1 (4)C6—Fe—C13—C1446.0 (8)
C10—Fe—C8—C781.5 (3)C8—Fe—C13—C14163.6 (4)
C15—Fe—C8—C747.7 (7)C7—Fe—C13—C14165.5 (6)
C13—Fe—C8—C7164.3 (3)C12—C13—C14—C150.1 (6)
C12—Fe—C8—C7123.2 (3)Fe—C13—C14—C1559.6 (4)
C6—Fe—C8—C736.9 (3)C12—C13—C14—Fe59.5 (4)
C14—Fe—C8—C7162.6 (6)C11—Fe—C14—C1537.9 (4)
C11—Fe—C8—C9159.9 (3)C9—Fe—C14—C15164.3 (4)
C10—Fe—C8—C937.6 (3)C10—Fe—C14—C15122.7 (4)
C15—Fe—C8—C9166.8 (5)C13—Fe—C14—C15118.9 (5)
C13—Fe—C8—C976.6 (4)C12—Fe—C14—C1581.9 (4)
C12—Fe—C8—C9117.7 (3)C6—Fe—C14—C1579.9 (4)
C6—Fe—C8—C982.2 (3)C8—Fe—C14—C15163.0 (6)
C14—Fe—C8—C943.5 (8)C7—Fe—C14—C1548.0 (8)
C7—Fe—C8—C9119.1 (4)C11—Fe—C14—C1381.0 (4)
C7—C8—C9—C100.4 (6)C9—Fe—C14—C1376.8 (4)
Fe—C8—C9—C1059.3 (3)C10—Fe—C14—C13118.5 (4)
C7—C8—C9—Fe59.7 (3)C15—Fe—C14—C13118.9 (5)
C11—Fe—C9—C10168.4 (5)C12—Fe—C14—C1337.0 (4)
C15—Fe—C9—C1046.2 (7)C6—Fe—C14—C13161.2 (3)
C13—Fe—C9—C10118.4 (3)C8—Fe—C14—C1344.1 (9)
C12—Fe—C9—C10159.9 (3)C7—Fe—C14—C13166.8 (5)
C6—Fe—C9—C1038.4 (3)C13—C14—C15—C110.1 (6)
C8—Fe—C9—C10119.4 (4)Fe—C14—C15—C1159.4 (4)
C14—Fe—C9—C1076.8 (4)C13—C14—C15—Fe59.5 (4)
C7—Fe—C9—C1082.1 (3)C12—C11—C15—C140.1 (6)
C11—Fe—C9—C849.1 (7)Fe—C11—C15—C1459.8 (4)
C10—Fe—C9—C8119.4 (4)C12—C11—C15—Fe59.8 (4)
C15—Fe—C9—C8165.5 (6)C11—Fe—C15—C14119.2 (5)
C13—Fe—C9—C8122.3 (3)C9—Fe—C15—C1441.2 (8)
C12—Fe—C9—C880.8 (4)C10—Fe—C15—C1475.7 (4)
C6—Fe—C9—C880.9 (3)C13—Fe—C15—C1438.0 (4)
C14—Fe—C9—C8163.8 (3)C12—Fe—C15—C1481.4 (4)
C7—Fe—C9—C837.3 (3)C6—Fe—C15—C14118.7 (4)
C8—C9—C10—C60.1 (5)C8—Fe—C15—C14164.7 (5)
Fe—C9—C10—C659.5 (3)C7—Fe—C15—C14160.7 (3)
C8—C9—C10—Fe59.4 (3)C9—Fe—C15—C11160.4 (6)
C7—C6—C10—C90.2 (5)C10—Fe—C15—C11165.1 (3)
C5—C6—C10—C9179.6 (4)C13—Fe—C15—C1181.2 (4)
Fe—C6—C10—C959.6 (3)C12—Fe—C15—C1137.8 (3)
C7—C6—C10—Fe59.8 (3)C6—Fe—C15—C11122.2 (3)
C5—C6—C10—Fe120.9 (4)C8—Fe—C15—C1145.5 (7)
C11—Fe—C10—C9166.3 (6)C14—Fe—C15—C11119.2 (5)
C15—Fe—C10—C9162.7 (3)C7—Fe—C15—C1180.2 (4)
C13—Fe—C10—C979.9 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O2i0.862.092.927 (6)164
C4—H4C···O2i0.962.583.170 (7)119
Symmetry code: (i) x+1/2, y+1/2, z+1.

Experimental details

Crystal data
Chemical formula[Fe(C5H5)(C10H13N2O2]
Mr314.16
Crystal system, space groupMonoclinic, C2/c
Temperature (K)295
a, b, c (Å)36.770 (7), 7.6040 (15), 10.366 (2)
β (°) 97.82 (3)
V3)2871.4 (10)
Z8
Radiation typeMo Kα
µ (mm1)1.05
Crystal size (mm)0.40 × 0.20 × 0.20
Data collection
DiffractometerEnraf–Nonius CAD4
diffractometer
Absorption correctionEmpirical (using intensity measurements)
via ψ scan (North et al., 1968)
Tmin, Tmax0.747, 0.803
No. of measured, independent and
observed [I > 2σ(I)] reflections
2848, 2804, 2178
Rint0.039
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.060, 0.184, 1.07
No. of reflections2804
No. of parameters177
No. of restraints13
H-atom treatmentH-atom parameters constrained
w = 1/[σ2(Fo2) + (0.098P)2 + 11.3526P]
where P = (Fo2 + 2Fc2)/3
Δρmax, Δρmin (e Å3)1.46, 0.76

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), CAD-4 Software, XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), PLATON.

Selected geometric parameters (Å, º) top
O1—C21.453 (6)N2—C51.290 (6)
O1—C31.313 (6)C1—C21.509 (8)
O2—C31.216 (6)C4—C51.503 (7)
N1—C31.353 (6)C5—C61.461 (6)
O1—C2—C1107.9 (6)N2—C5—C4125.4 (4)
O1—C3—O2124.2 (5)N2—C5—C6115.4 (4)
O1—C3—N1114.3 (4)C4—C5—C6119.2 (4)
O2—C3—N1121.6 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O2i0.862.092.927 (6)164
Symmetry code: (i) x+1/2, y+1/2, z+1.
 

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