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Molecules of the title compound, [Fe(C5H5)(C16H16NO2)], are stabilized by intramolecular hydrogen bonds (N—H...O=C) and are linked by intermolecular hydrogen bonds (O—H...O=C) to form centrosymmetric R22(16) dimers.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805009104/ng6111sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805009104/ng6111Isup2.hkl
Contains datablock I

CCDC reference: 272047

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.008 Å
  • R factor = 0.056
  • wR factor = 0.177
  • Data-to-parameter ratio = 14.5

checkCIF/PLATON results

No syntax errors found



Alert level C 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 1 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 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

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: WinGX (Farrugia, 2005); software used to prepare material for publication: WinGX.

1-ferrocenyl-3-(2-hydroxymethylphenyl)aminobut-2-en-1-one top
Crystal data top
[Fe(C5H5)(C16H16NO2)]F(000) = 784
Mr = 375.24Dx = 1.416 Mg m3
Monoclinic, P21/nMelting point = 416–417 K
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71073 Å
a = 15.590 (3) ÅCell parameters from 25 reflections
b = 7.5280 (15) Åθ = 9–12°
c = 15.755 (3) ŵ = 0.87 mm1
β = 107.85 (3)°T = 293 K
V = 1760.0 (7) Å3Block, red
Z = 40.3 × 0.2 × 0.1 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer
2158 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.047
Graphite monochromatorθmax = 26.0°, θmin = 1.6°
ω/2θ scansh = 019
Absorption correction: empirical (using intensity measurements)
via ψ scan (North et al., 1968)
k = 09
Tmin = 0.801, Tmax = 0.911l = 1919
3535 measured reflections3 standard reflections every 200 reflections
3407 independent reflections intensity decay: 0.1%
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)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.177H atoms treated by a mixture of independent and constrained refinement
S = 0.96 w = 1/[σ2(Fo2) + (0.0756P)2 + 3.6852P]
where P = (Fo2 + 2Fc2)/3
3407 reflections(Δ/σ)max = 0.001
235 parametersΔρmax = 0.46 e Å3
3 restraintsΔρmin = 0.36 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
Fe10.56088 (5)0.72490 (9)0.14724 (5)0.0430 (3)
O10.4968 (3)0.5581 (5)0.3457 (2)0.0595 (11)
O20.3161 (3)0.4019 (6)0.5756 (3)0.0659 (11)
H2O0.3730 (10)0.403 (11)0.599 (5)0.10 (3)*
N10.4031 (3)0.2650 (6)0.3574 (3)0.0488 (11)
H1N0.439 (3)0.343 (5)0.388 (3)0.048 (16)*
C10.3937 (4)0.1762 (7)0.4588 (4)0.0585 (15)
H10.41080.29250.45240.070*
C20.4108 (4)0.0438 (7)0.4059 (4)0.0545 (14)
H20.44030.07080.36440.065*
C30.3843 (3)0.1290 (6)0.4139 (3)0.0418 (12)
C40.3417 (3)0.1734 (6)0.4759 (3)0.0395 (11)
C50.3253 (4)0.0367 (7)0.5300 (4)0.0486 (13)
H50.29650.06290.57230.058*
C60.3514 (4)0.1362 (7)0.5210 (4)0.0511 (13)
H60.34030.22540.55710.061*
C70.3138 (4)0.3618 (7)0.4883 (4)0.0541 (14)
H7A0.35340.44320.47050.065*
H7B0.25310.38120.44890.065*
C80.3680 (3)0.2825 (7)0.2707 (3)0.0460 (12)
C90.2999 (4)0.1465 (8)0.2214 (4)0.0684 (17)
H9A0.32980.03530.22030.103*
H9B0.27160.18630.16140.103*
H9C0.25510.13120.25110.103*
C100.3915 (3)0.4198 (7)0.2250 (3)0.0435 (12)
H100.36540.42220.16340.052*
C110.4520 (3)0.5570 (6)0.2638 (3)0.0417 (12)
C120.4637 (3)0.7070 (6)0.2084 (3)0.0424 (11)
C130.4241 (4)0.7291 (7)0.1141 (4)0.0479 (12)
H130.38470.64980.07620.057*
C140.4545 (4)0.8907 (7)0.0880 (4)0.0603 (16)
H140.43880.93570.03020.072*
C150.5128 (4)0.9720 (7)0.1644 (5)0.0641 (17)
H150.54181.08060.16600.077*
C160.5199 (4)0.8602 (7)0.2385 (4)0.0502 (13)
H160.55500.88220.29690.060*
C170.6930 (4)0.6656 (9)0.2089 (5)0.0643 (16)
H170.72700.70140.26580.077*
C180.6847 (4)0.7587 (8)0.1298 (5)0.0669 (18)
H180.71190.86660.12500.080*
C190.6271 (4)0.6591 (8)0.0581 (4)0.0621 (16)
H190.60970.69000.00200.075*
C200.6009 (4)0.5034 (7)0.0951 (4)0.0542 (14)
H200.56350.41390.06340.065*
C210.6416 (4)0.5087 (8)0.1881 (4)0.0563 (14)
H210.63550.42350.22860.068*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.0521 (4)0.0349 (4)0.0486 (4)0.0022 (3)0.0250 (3)0.0008 (3)
O10.084 (3)0.053 (2)0.041 (2)0.025 (2)0.018 (2)0.0001 (17)
O20.080 (3)0.057 (3)0.067 (3)0.013 (2)0.033 (3)0.012 (2)
N10.066 (3)0.043 (3)0.039 (2)0.017 (2)0.018 (2)0.000 (2)
C10.070 (4)0.036 (3)0.072 (4)0.004 (3)0.026 (3)0.006 (3)
C20.063 (4)0.047 (3)0.063 (4)0.006 (3)0.032 (3)0.007 (3)
C30.048 (3)0.031 (3)0.050 (3)0.008 (2)0.019 (2)0.001 (2)
C40.043 (3)0.032 (3)0.043 (3)0.006 (2)0.012 (2)0.001 (2)
C50.054 (3)0.046 (3)0.050 (3)0.007 (3)0.023 (3)0.002 (2)
C60.058 (3)0.035 (3)0.060 (3)0.005 (2)0.019 (3)0.013 (3)
C70.069 (4)0.035 (3)0.061 (4)0.003 (3)0.023 (3)0.007 (3)
C80.048 (3)0.044 (3)0.048 (3)0.004 (2)0.019 (2)0.000 (2)
C90.070 (4)0.060 (4)0.066 (4)0.026 (3)0.007 (3)0.005 (3)
C100.049 (3)0.043 (3)0.040 (3)0.000 (2)0.016 (2)0.003 (2)
C110.051 (3)0.039 (3)0.042 (3)0.001 (2)0.024 (2)0.000 (2)
C120.052 (3)0.033 (2)0.051 (3)0.003 (2)0.027 (2)0.000 (2)
C130.054 (3)0.040 (3)0.056 (3)0.003 (2)0.025 (3)0.006 (2)
C140.068 (4)0.051 (4)0.074 (4)0.011 (3)0.039 (3)0.023 (3)
C150.083 (4)0.030 (3)0.096 (5)0.007 (3)0.053 (4)0.004 (3)
C160.066 (4)0.039 (3)0.054 (3)0.002 (3)0.031 (3)0.006 (2)
C170.051 (3)0.069 (4)0.075 (4)0.003 (3)0.022 (3)0.008 (3)
C180.061 (4)0.059 (4)0.099 (5)0.014 (3)0.052 (4)0.001 (4)
C190.071 (4)0.066 (4)0.064 (4)0.002 (3)0.043 (3)0.004 (3)
C200.056 (3)0.046 (3)0.059 (4)0.011 (3)0.017 (3)0.012 (3)
C210.057 (3)0.051 (3)0.061 (4)0.010 (3)0.018 (3)0.007 (3)
Geometric parameters (Å, º) top
Fe1—C122.034 (5)C14—C151.407 (9)
Fe1—C132.034 (5)C15—C161.416 (8)
Fe1—C142.057 (5)C17—C181.401 (9)
Fe1—C152.054 (6)C17—C211.409 (8)
Fe1—C162.019 (5)C18—C191.423 (9)
Fe1—C172.040 (6)C19—C201.423 (8)
Fe1—C182.047 (5)C20—C211.407 (7)
Fe1—C192.043 (5)C1—H10.9300
Fe1—C202.039 (5)C2—H20.9300
Fe1—C212.037 (6)C5—H50.9300
N1—C31.444 (6)C6—H60.9300
N1—C81.314 (6)C7—H7A0.9700
O1—C111.265 (6)C7—H7B0.9700
O2—C71.399 (7)C9—H9A0.9600
C1—C61.371 (7)C9—H9B0.9600
C1—C21.377 (7)C9—H9C0.9600
C2—C31.382 (7)C13—H130.9300
C3—C41.380 (7)C14—H140.9300
C4—C51.410 (7)C15—H150.9300
C4—C71.514 (7)C16—H160.9300
C5—C61.384 (7)C17—H170.9300
C8—C91.507 (7)C18—H180.9300
C8—C101.372 (7)C19—H190.9300
C10—C111.406 (7)C20—H200.9300
C11—C121.472 (7)C21—H210.9300
C12—C131.433 (7)O2—H2O0.85 (4)
C12—C161.438 (7)N1—H1N0.85 (4)
C13—C141.412 (7)
C12—Fe1—C1469.0 (2)C3—C4—C7122.6 (4)
C12—Fe1—C1569.1 (2)C5—C4—C7119.5 (4)
C12—Fe1—C17123.4 (2)C6—C5—C4120.7 (5)
C12—Fe1—C18160.3 (3)C1—C6—C5120.1 (5)
C12—Fe1—C19156.4 (2)O2—C7—C4114.1 (4)
C12—Fe1—C20120.1 (2)O2—C7—H7A109
C12—Fe1—C21106.0 (2)O2—C7—H7B109
C13—Fe1—C1241.3 (2)C4—C7—H7A109
C13—Fe1—C1440.4 (2)C4—C7—H7B109
C13—Fe1—C1567.9 (2)N1—C8—C10121.9 (5)
C13—Fe1—C17162.2 (2)N1—C8—C9118.1 (5)
C13—Fe1—C18157.0 (2)C10—C8—C9120.0 (5)
C13—Fe1—C19122.5 (2)C8—C9—H9A109
C13—Fe1—C20109.6 (2)C8—C9—H9B109
C13—Fe1—C21126.2 (2)C8—C9—H9C109
C15—Fe1—C1440.0 (2)C8—C10—C11125.2 (5)
C16—Fe1—C1241.6 (2)O1—C11—C10122.4 (4)
C16—Fe1—C1368.8 (2)O1—C11—C12118.0 (4)
C16—Fe1—C1468.3 (2)C10—C11—C12119.6 (4)
C16—Fe1—C1540.7 (2)C13—C12—C16105.9 (4)
C16—Fe1—C17105.4 (2)C13—C12—C11127.7 (5)
C16—Fe1—C18123.4 (3)C16—C12—C11126.4 (5)
C16—Fe1—C19161.6 (2)C13—C12—Fe169.4 (3)
C16—Fe1—C20154.4 (2)C16—C12—Fe168.7 (3)
C16—Fe1—C21118.6 (2)C11—C12—Fe1125.3 (3)
C17—Fe1—C14154.8 (3)C14—C13—C12109.0 (5)
C17—Fe1—C15119.4 (3)C14—C13—Fe170.7 (3)
C17—Fe1—C1840.1 (2)C12—C13—Fe169.4 (3)
C17—Fe1—C1968.0 (3)C15—C14—C13108.2 (5)
C18—Fe1—C14121.7 (2)C15—C14—Fe169.9 (3)
C18—Fe1—C15107.6 (2)C13—C14—Fe168.9 (3)
C19—Fe1—C14110.0 (3)C14—C15—C16108.3 (5)
C19—Fe1—C15126.3 (2)C14—C15—Fe170.1 (3)
C19—Fe1—C1840.7 (2)C16—C15—Fe168.3 (3)
C20—Fe1—C14128.1 (3)C12—C16—H16126
C20—Fe1—C15164.3 (2)C15—C16—C12108.6 (5)
C20—Fe1—C1767.9 (2)C15—C16—Fe171.0 (3)
C20—Fe1—C1868.3 (2)C12—C16—Fe169.8 (3)
C20—Fe1—C1940.8 (2)C18—C17—C21108.7 (6)
C21—Fe1—C14164.2 (3)C18—C17—Fe170.2 (3)
C21—Fe1—C15153.8 (3)C21—C17—Fe169.7 (3)
C21—Fe1—C1740.4 (2)C17—C18—C19107.9 (5)
C21—Fe1—C1868.0 (2)C17—C18—Fe169.7 (3)
C21—Fe1—C1968.3 (2)C17—C18—H18126
C21—Fe1—C2040.4 (2)C19—C18—Fe169.5 (3)
C3—N1—C8127.8 (4)C18—C19—C20107.4 (5)
C3—N1—H1N111 (3)C18—C19—Fe169.8 (3)
C8—N1—H1N121 (3)C20—C19—Fe169.5 (3)
C2—C1—H1120C21—C20—C19108.0 (5)
C6—C1—C2119.9 (5)C21—C20—Fe169.7 (3)
C1—C2—C3120.5 (5)C19—C20—Fe169.7 (3)
C2—C3—N1119.2 (5)C20—C21—C17108.0 (5)
C4—C3—C2121.0 (5)C20—C21—Fe169.9 (3)
C4—C3—N1119.8 (4)C17—C21—Fe169.9 (3)
C3—C4—C5117.9 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1n···O10.85 (4)2.06 (4)2.684 (6)130 (4)
O2—H2o···O1i0.85 (4)1.97 (4)2.814 (7)172 (7)
C7—H7a···N10.972.532.913 (8)103
Symmetry code: (i) x+1, y+1, z+1.
 

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