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In the title compound, [Fe(C5H5)(C18H16N3O3)], the propene plane is tilted from its parent cyclopentadienyl ring by a small dihedral angle [17.9 (5)°], whereas the triazole and dimethoxy­phenyl groups are nearly perpendicular to the propene plane [dihedral angles 75.9 (2) and 67.9 (2)°, respectively]. The cyclo­penta­dienyl rings exhibit an almost eclipsed geometry.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805038699/xu6063sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805038699/xu6063Isup2.hkl
Contains datablock I

CCDC reference: 296708

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.049
  • wR factor = 0.129
  • Data-to-parameter ratio = 15.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for Fe1
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 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

We are interested in 1H-1,2,4-triazole derivatives because of their biological activities (Moreno-Manas et al., 1992; Chu et al., 1999; Liu et al., 1998). As part of an investigation on ferrocenyl-triazole derivatives (Fang et al., 2003; Jin et al., 2005), we report here the structure of the title compound, (I).

The molecular structure of (I) is shown in Fig. 1. The Fe—C bond lengths range from 2.021 (3) to 2.042 (3) Å. The Fe1···Cg1 and Fe1···Cg2 distances are 1.634 (2) and 1.647 (2) Å, respectively (where Cg is the centroid of the five rings of the ferrocene). The cyclopentadienyl rings of the ferrocene are in an almost eclipsed geometry. While the propene plane tilts to the η(C5H4) ring of the ferrocene with a small dihedral angle of 17.9 (5)°, the dimethoxyphenyl and triazole rings are nearly perpendicular to the propene plane, the dihedral angles being 75.9 (2) and 67.9 (2)°, respectively.

Experimental top

1-(2,5-Dimethoxyphenyl)-2-(1H-1,2,4-triazol-1-yl)-ethanone (10 mmol) and ferrocenecarboxaldehyde (11 mmol) were dissolved in a dry toluene solution (50 ml). To the solution five drops of piperidine and five drops of glacial acetic acid were added at room temperature under a nitrogen atmosphere. The mixture was refluxed for 6 h, meanwhile the water generated in the reaction was evaporated. The toluene was evaporated under reduced pressure, and the residue was then purified by column chromatography on silica gel with petroleum ether/ethyl acetate (v/v = 4:1). Recrystallization from a petroleum ether/ethyl acetate solution (v/v = 3:1) gave single crystals of (I) (yield 70.0%).

Refinement top

Methyl H atoms were placed in calculated positions with C—H = 0.96 Å and torsion angles refined to fit the electron density, with Uiso(H) = 1.5Ueq(C). Other H atoms were placed in calculated positions with C—H = 0.93 Å and refined using a riding model, with Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: SMART (Bruker,1998); cell refinement: SAINT; data reduction: SAINT (Bruker,1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), with 30% probability displacement ellipsoids (arbitrary spheres for H atoms).
1-(2,5-Dimethoxyphenyl)-3-ferrocenyl-2-(1H-1,2,4-triazol-1-yl)prop-2-en-1-one top
Crystal data top
[Fe(C5H5)(C18H16N3O3)]F(000) = 920
Mr = 443.28Dx = 1.433 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2484 reflections
a = 7.292 (2) Åθ = 2.5–24.3°
b = 20.226 (5) ŵ = 0.76 mm1
c = 13.956 (4) ÅT = 294 K
β = 93.669 (5)°Block, black
V = 2054.2 (10) Å30.24 × 0.22 × 0.18 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
4181 independent reflections
Radiation source: fine-focus sealed tube2551 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.054
ϕ and ω scansθmax = 26.5°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 89
Tmin = 0.826, Tmax = 0.878k = 2225
11212 measured reflectionsl = 1117
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)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.129H-atom parameters constrained
S = 0.99 w = 1/[σ2(Fo2) + (0.0659P)2]
where P = (Fo2 + 2Fc2)/3
4181 reflections(Δ/σ)max = 0.002
273 parametersΔρmax = 0.40 e Å3
0 restraintsΔρmin = 0.53 e Å3
Crystal data top
[Fe(C5H5)(C18H16N3O3)]V = 2054.2 (10) Å3
Mr = 443.28Z = 4
Monoclinic, P21/nMo Kα radiation
a = 7.292 (2) ŵ = 0.76 mm1
b = 20.226 (5) ÅT = 294 K
c = 13.956 (4) Å0.24 × 0.22 × 0.18 mm
β = 93.669 (5)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
4181 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2551 reflections with I > 2σ(I)
Tmin = 0.826, Tmax = 0.878Rint = 0.054
11212 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0490 restraints
wR(F2) = 0.129H-atom parameters constrained
S = 0.99Δρmax = 0.40 e Å3
4181 reflectionsΔρmin = 0.53 e Å3
273 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
xyzUiso*/Ueq
Fe10.22765 (6)1.01115 (2)0.29240 (4)0.03427 (18)
O10.5728 (3)0.83702 (11)0.5326 (2)0.0584 (8)
O20.1496 (3)0.76394 (11)0.61889 (17)0.0489 (6)
O30.6221 (3)0.57989 (11)0.47810 (19)0.0522 (7)
N10.1376 (3)0.81187 (12)0.40552 (19)0.0315 (6)
N20.1749 (4)0.77970 (14)0.3239 (2)0.0469 (8)
N30.1227 (4)0.76715 (16)0.3551 (2)0.0562 (9)
C10.4268 (4)0.81071 (15)0.5090 (2)0.0346 (8)
C20.3994 (4)0.73906 (15)0.5280 (2)0.0305 (7)
C30.5257 (4)0.69431 (16)0.4930 (2)0.0324 (8)
H30.61980.70950.45680.039*
C40.5103 (4)0.62812 (17)0.5122 (2)0.0378 (9)
C50.3701 (5)0.60550 (17)0.5664 (3)0.0439 (9)
H50.35880.56050.57810.053*
C60.2472 (4)0.64926 (17)0.6030 (2)0.0438 (9)
H60.15590.63380.64080.053*
C70.2600 (4)0.71656 (16)0.5834 (2)0.0348 (8)
C80.0054 (5)0.7428 (2)0.6765 (3)0.0601 (11)
H8A0.07770.71470.63920.090*
H8B0.05980.78070.69800.090*
H8C0.05700.71880.73120.090*
C90.7755 (5)0.60015 (18)0.4297 (3)0.0624 (12)
H9A0.73520.62460.37330.094*
H9B0.84350.56200.41160.094*
H9C0.85270.62770.47120.094*
C100.2776 (4)0.84912 (15)0.4585 (2)0.0299 (7)
C110.0398 (4)0.80330 (16)0.4223 (3)0.0445 (9)
H110.09610.82070.47460.053*
C120.0140 (6)0.75470 (19)0.2965 (3)0.0555 (11)
H120.00480.73010.24050.067*
C130.2768 (4)0.91498 (15)0.4592 (2)0.0328 (8)
H130.37030.93460.49780.039*
C140.1516 (4)0.96037 (16)0.4088 (2)0.0334 (8)
C150.0244 (4)0.94979 (17)0.3284 (3)0.0420 (9)
H150.00410.90920.29980.050*
C160.0507 (5)1.01155 (19)0.2996 (3)0.0523 (10)
H160.13801.01870.24910.063*
C170.0299 (5)1.06069 (18)0.3608 (3)0.0525 (11)
H170.00421.10570.35730.063*
C180.1552 (5)1.03047 (16)0.4276 (3)0.0434 (9)
H180.22751.05180.47540.052*
C190.3665 (6)0.9642 (2)0.1908 (3)0.0606 (11)
H190.34820.92070.17090.073*
C200.2777 (5)1.0194 (2)0.1511 (3)0.0542 (10)
H200.18981.01910.09980.065*
C210.3416 (5)1.0753 (2)0.2004 (3)0.0545 (11)
H210.30451.11860.18790.065*
C220.4726 (5)1.0548 (2)0.2728 (3)0.0609 (12)
H220.53661.08200.31700.073*
C230.4890 (5)0.9857 (2)0.2663 (3)0.0636 (12)
H230.56680.95900.30490.076*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.0211 (3)0.0380 (3)0.0451 (3)0.0006 (2)0.0126 (2)0.0024 (2)
O10.0296 (13)0.0420 (15)0.102 (2)0.0102 (12)0.0110 (14)0.0016 (14)
O20.0420 (15)0.0492 (15)0.0581 (16)0.0013 (12)0.0243 (13)0.0026 (12)
O30.0454 (15)0.0387 (14)0.0743 (19)0.0054 (11)0.0180 (14)0.0042 (13)
N10.0248 (14)0.0321 (15)0.0378 (16)0.0040 (11)0.0035 (12)0.0004 (12)
N20.0438 (19)0.0548 (19)0.0415 (18)0.0041 (15)0.0026 (15)0.0107 (15)
N30.045 (2)0.055 (2)0.067 (2)0.0186 (16)0.0106 (19)0.0046 (18)
C10.0287 (17)0.0350 (18)0.041 (2)0.0030 (15)0.0082 (15)0.0001 (15)
C20.0233 (16)0.0344 (18)0.0335 (18)0.0028 (13)0.0012 (14)0.0013 (15)
C30.0203 (17)0.039 (2)0.038 (2)0.0042 (13)0.0042 (15)0.0042 (15)
C40.0335 (19)0.037 (2)0.043 (2)0.0004 (15)0.0010 (17)0.0024 (16)
C50.045 (2)0.038 (2)0.049 (2)0.0015 (16)0.0112 (18)0.0117 (17)
C60.034 (2)0.049 (2)0.049 (2)0.0057 (16)0.0097 (17)0.0145 (18)
C70.0285 (18)0.042 (2)0.0337 (19)0.0016 (15)0.0035 (15)0.0039 (16)
C80.046 (2)0.068 (3)0.071 (3)0.0032 (19)0.034 (2)0.008 (2)
C90.054 (3)0.057 (3)0.079 (3)0.004 (2)0.031 (2)0.004 (2)
C100.0239 (16)0.0301 (18)0.0366 (19)0.0069 (13)0.0080 (14)0.0011 (15)
C110.0278 (18)0.048 (2)0.058 (3)0.0104 (16)0.0080 (18)0.0020 (19)
C120.060 (3)0.052 (2)0.052 (3)0.001 (2)0.017 (2)0.012 (2)
C130.0261 (17)0.037 (2)0.0359 (19)0.0094 (14)0.0069 (15)0.0007 (15)
C140.0268 (17)0.0325 (18)0.043 (2)0.0020 (14)0.0151 (16)0.0028 (16)
C150.0201 (17)0.045 (2)0.061 (2)0.0079 (15)0.0049 (17)0.0066 (18)
C160.0211 (17)0.065 (3)0.072 (3)0.0053 (18)0.0120 (18)0.023 (2)
C170.046 (2)0.043 (2)0.073 (3)0.0144 (19)0.034 (2)0.009 (2)
C180.043 (2)0.039 (2)0.051 (2)0.0009 (16)0.0240 (18)0.0007 (17)
C190.045 (2)0.067 (3)0.073 (3)0.004 (2)0.027 (2)0.019 (2)
C200.040 (2)0.083 (3)0.041 (2)0.002 (2)0.0126 (18)0.002 (2)
C210.047 (2)0.055 (3)0.064 (3)0.0104 (19)0.022 (2)0.014 (2)
C220.038 (2)0.091 (4)0.055 (3)0.026 (2)0.018 (2)0.009 (2)
C230.025 (2)0.098 (4)0.070 (3)0.017 (2)0.018 (2)0.020 (3)
Geometric parameters (Å, º) top
Fe1—C152.021 (3)C6—H60.9300
Fe1—C222.026 (4)C8—H8A0.9600
Fe1—C142.029 (3)C8—H8B0.9600
Fe1—C232.030 (4)C8—H8C0.9600
Fe1—C182.030 (4)C9—H9A0.9600
Fe1—C192.031 (4)C9—H9B0.9600
Fe1—C202.036 (4)C9—H9C0.9600
Fe1—C162.039 (3)C10—C131.332 (4)
Fe1—C212.039 (4)C11—H110.9300
Fe1—C172.042 (3)C12—H120.9300
O1—C11.216 (4)C13—C141.445 (4)
O2—C71.365 (4)C13—H130.9300
O2—C81.430 (4)C14—C151.426 (4)
O3—C41.376 (4)C14—C181.442 (5)
O3—C91.405 (4)C15—C161.412 (5)
N1—C111.340 (4)C15—H150.9300
N1—N21.354 (4)C16—C171.414 (5)
N1—C101.436 (4)C16—H160.9300
N2—C121.312 (4)C17—C181.403 (5)
N3—C111.307 (4)C17—H170.9300
N3—C121.353 (5)C18—H180.9300
C1—C21.489 (4)C19—C201.389 (5)
C1—C101.478 (4)C19—C231.406 (6)
C2—C71.393 (4)C19—H190.9300
C2—C31.401 (4)C20—C211.388 (5)
C3—C41.371 (4)C20—H200.9300
C3—H30.9300C21—C221.407 (5)
C4—C51.387 (4)C21—H210.9300
C5—C61.381 (5)C22—C231.407 (6)
C5—H50.9300C22—H220.9300
C6—C71.392 (4)C23—H230.9300
C15—Fe1—C22165.40 (17)O3—C9—H9A109.5
C15—Fe1—C1441.22 (13)O3—C9—H9B109.5
C22—Fe1—C14128.08 (16)H9A—C9—H9B109.5
C15—Fe1—C23126.92 (17)O3—C9—H9C109.5
C22—Fe1—C2340.59 (16)H9A—C9—H9C109.5
C14—Fe1—C23108.86 (15)H9B—C9—H9C109.5
C15—Fe1—C1869.44 (15)C13—C10—N1121.7 (3)
C22—Fe1—C18108.98 (16)C13—C10—C1121.7 (3)
C14—Fe1—C1841.62 (13)N1—C10—C1116.6 (3)
C23—Fe1—C18121.27 (17)N3—C11—N1110.8 (3)
C15—Fe1—C19107.02 (16)N3—C11—H11124.6
C22—Fe1—C1968.07 (17)N1—C11—H11124.6
C14—Fe1—C19119.76 (16)N2—C12—N3115.6 (3)
C23—Fe1—C1940.51 (16)N2—C12—H12122.2
C18—Fe1—C19155.57 (17)N3—C12—H12122.2
C15—Fe1—C20118.10 (16)C10—C13—C14129.4 (3)
C22—Fe1—C2067.63 (16)C10—C13—H13115.3
C14—Fe1—C20153.19 (15)C14—C13—H13115.3
C23—Fe1—C2067.54 (16)C15—C14—C18107.1 (3)
C18—Fe1—C20163.42 (15)C15—C14—C13130.3 (3)
C19—Fe1—C2039.95 (16)C18—C14—C13122.1 (3)
C15—Fe1—C1640.71 (13)C15—C14—Fe169.10 (18)
C22—Fe1—C16153.36 (18)C18—C14—Fe169.23 (18)
C14—Fe1—C1668.82 (14)C13—C14—Fe1121.0 (2)
C23—Fe1—C16163.55 (18)C16—C15—C14108.2 (3)
C18—Fe1—C1668.56 (16)C16—C15—Fe170.32 (19)
C19—Fe1—C16125.36 (18)C14—C15—Fe169.68 (18)
C20—Fe1—C16106.74 (17)C16—C15—H15125.9
C15—Fe1—C21151.89 (16)C14—C15—H15125.9
C22—Fe1—C2140.51 (15)Fe1—C15—H15125.7
C14—Fe1—C21165.79 (16)C15—C16—C17108.1 (3)
C23—Fe1—C2167.84 (17)C15—C16—Fe168.98 (18)
C18—Fe1—C21127.13 (15)C17—C16—Fe169.9 (2)
C19—Fe1—C2167.43 (18)C15—C16—H16125.9
C20—Fe1—C2139.83 (15)C17—C16—H16125.9
C16—Fe1—C21118.41 (16)Fe1—C16—H16126.8
C15—Fe1—C1768.55 (15)C18—C17—C16108.9 (3)
C22—Fe1—C17120.26 (18)C18—C17—Fe169.4 (2)
C14—Fe1—C1768.72 (14)C16—C17—Fe169.6 (2)
C23—Fe1—C17155.20 (19)C18—C17—H17125.6
C18—Fe1—C1740.32 (14)C16—C17—H17125.6
C19—Fe1—C17162.67 (18)Fe1—C17—H17127.0
C20—Fe1—C17126.03 (16)C17—C18—C14107.7 (3)
C16—Fe1—C1740.54 (15)C17—C18—Fe170.3 (2)
C21—Fe1—C17108.10 (16)C14—C18—Fe169.14 (18)
C7—O2—C8117.8 (3)C17—C18—H18126.2
C4—O3—C9117.9 (3)C14—C18—H18126.2
C11—N1—N2109.5 (3)Fe1—C18—H18126.0
C11—N1—C10129.8 (3)C20—C19—C23107.9 (4)
N2—N1—C10120.7 (3)C20—C19—Fe170.2 (2)
C12—N2—N1101.9 (3)C23—C19—Fe169.7 (2)
C11—N3—C12102.3 (3)C20—C19—H19126.0
O1—C1—C10120.2 (3)C23—C19—H19126.0
O1—C1—C2120.2 (3)Fe1—C19—H19125.6
C10—C1—C2119.5 (3)C21—C20—C19108.9 (4)
C7—C2—C3120.1 (3)C21—C20—Fe170.2 (2)
C7—C2—C1121.9 (3)C19—C20—Fe169.8 (2)
C3—C2—C1117.9 (3)C21—C20—H20125.6
C4—C3—C2119.9 (3)C19—C20—H20125.6
C4—C3—H3120.1Fe1—C20—H20126.0
C2—C3—H3120.1C20—C21—C22108.0 (4)
C3—C4—O3124.5 (3)C20—C21—Fe170.0 (2)
C3—C4—C5120.1 (3)C22—C21—Fe169.3 (2)
O3—C4—C5115.4 (3)C20—C21—H21126.0
C6—C5—C4120.6 (3)C22—C21—H21126.0
C6—C5—H5119.7Fe1—C21—H21126.3
C4—C5—H5119.7C23—C22—C21107.6 (4)
C5—C6—C7120.0 (3)C23—C22—Fe169.8 (2)
C5—C6—H6120.0C21—C22—Fe170.2 (2)
C7—C6—H6120.0C23—C22—H22126.2
O2—C7—C2116.1 (3)C21—C22—H22126.2
O2—C7—C6124.5 (3)Fe1—C22—H22125.3
C2—C7—C6119.3 (3)C19—C23—C22107.7 (4)
O2—C8—H8A109.5C19—C23—Fe169.8 (2)
O2—C8—H8B109.5C22—C23—Fe169.6 (2)
H8A—C8—H8B109.5C19—C23—H23126.2
O2—C8—H8C109.5C22—C23—H23126.2
H8A—C8—H8C109.5Fe1—C23—H23126.0
H8B—C8—H8C109.5
C11—N1—N2—C121.0 (4)C19—Fe1—C17—C1640.8 (6)
C10—N1—N2—C12177.7 (3)C20—Fe1—C17—C1672.4 (3)
O1—C1—C2—C7121.6 (4)C21—Fe1—C17—C16112.8 (2)
C10—C1—C2—C760.4 (4)C16—C17—C18—C140.7 (4)
O1—C1—C2—C354.7 (5)Fe1—C17—C18—C1459.3 (2)
C10—C1—C2—C3123.3 (3)C16—C17—C18—Fe158.5 (2)
C7—C2—C3—C40.9 (5)C15—C14—C18—C171.1 (3)
C1—C2—C3—C4177.3 (3)C13—C14—C18—C17174.3 (3)
C2—C3—C4—O3177.2 (3)Fe1—C14—C18—C1760.0 (2)
C2—C3—C4—C50.1 (5)C15—C14—C18—Fe158.9 (2)
C9—O3—C4—C37.8 (5)C13—C14—C18—Fe1114.3 (3)
C9—O3—C4—C5174.8 (3)C15—Fe1—C18—C1780.7 (2)
C3—C4—C5—C61.3 (5)C22—Fe1—C18—C17114.7 (3)
O3—C4—C5—C6178.8 (3)C14—Fe1—C18—C17118.8 (3)
C4—C5—C6—C71.9 (5)C23—Fe1—C18—C17157.8 (2)
C8—O2—C7—C2179.7 (3)C19—Fe1—C18—C17166.7 (4)
C8—O2—C7—C63.0 (5)C20—Fe1—C18—C1739.5 (6)
C3—C2—C7—O2176.5 (3)C16—Fe1—C18—C1737.0 (2)
C1—C2—C7—O20.3 (5)C21—Fe1—C18—C1773.1 (3)
C3—C2—C7—C60.4 (5)C15—Fe1—C18—C1438.07 (18)
C1—C2—C7—C6176.6 (3)C22—Fe1—C18—C14126.5 (2)
C5—C6—C7—O2177.6 (3)C23—Fe1—C18—C1483.4 (2)
C5—C6—C7—C21.0 (5)C19—Fe1—C18—C1447.9 (4)
C11—N1—C10—C1370.9 (4)C20—Fe1—C18—C14158.3 (5)
N2—N1—C10—C13107.5 (3)C16—Fe1—C18—C1481.8 (2)
C11—N1—C10—C1111.5 (4)C21—Fe1—C18—C14168.1 (2)
N2—N1—C10—C170.1 (4)C17—Fe1—C18—C14118.8 (3)
O1—C1—C10—C1317.8 (5)C15—Fe1—C19—C20113.7 (3)
C2—C1—C10—C13164.1 (3)C22—Fe1—C19—C2080.9 (3)
O1—C1—C10—N1159.8 (3)C14—Fe1—C19—C20156.7 (2)
C2—C1—C10—N118.3 (4)C23—Fe1—C19—C20118.8 (4)
C12—N3—C11—N10.4 (4)C18—Fe1—C19—C20168.7 (3)
N2—N1—C11—N30.4 (4)C16—Fe1—C19—C2072.7 (3)
C10—N1—C11—N3178.2 (3)C21—Fe1—C19—C2037.0 (2)
N1—N2—C12—N31.3 (4)C17—Fe1—C19—C2041.3 (6)
C11—N3—C12—N21.1 (5)C15—Fe1—C19—C23127.5 (3)
N1—C10—C13—C142.6 (5)C22—Fe1—C19—C2337.9 (2)
C1—C10—C13—C14174.9 (3)C14—Fe1—C19—C2384.5 (3)
C10—C13—C14—C1517.1 (5)C18—Fe1—C19—C2349.9 (5)
C10—C13—C14—C18171.3 (3)C20—Fe1—C19—C23118.8 (4)
C10—C13—C14—Fe1105.0 (3)C16—Fe1—C19—C23168.5 (2)
C22—Fe1—C14—C15166.2 (2)C21—Fe1—C19—C2381.8 (3)
C23—Fe1—C14—C15125.0 (2)C17—Fe1—C19—C23160.1 (5)
C18—Fe1—C14—C15118.8 (3)C23—C19—C20—C210.2 (4)
C19—Fe1—C14—C1581.9 (2)Fe1—C19—C20—C2159.5 (3)
C20—Fe1—C14—C1547.6 (4)C23—C19—C20—Fe159.7 (3)
C16—Fe1—C14—C1537.7 (2)C15—Fe1—C20—C21157.1 (2)
C21—Fe1—C14—C15160.9 (6)C22—Fe1—C20—C2137.8 (2)
C17—Fe1—C14—C1581.3 (2)C14—Fe1—C20—C21169.4 (3)
C15—Fe1—C14—C18118.8 (3)C23—Fe1—C20—C2181.9 (3)
C22—Fe1—C14—C1874.9 (3)C18—Fe1—C20—C2143.6 (6)
C23—Fe1—C14—C18116.2 (2)C19—Fe1—C20—C21119.9 (4)
C19—Fe1—C14—C18159.3 (2)C16—Fe1—C20—C21114.5 (3)
C20—Fe1—C14—C18166.5 (3)C17—Fe1—C20—C2174.2 (3)
C16—Fe1—C14—C1881.1 (2)C15—Fe1—C20—C1983.1 (3)
C21—Fe1—C14—C1842.1 (6)C22—Fe1—C20—C1982.1 (3)
C17—Fe1—C14—C1837.5 (2)C14—Fe1—C20—C1949.6 (4)
C15—Fe1—C14—C13125.3 (4)C23—Fe1—C20—C1938.0 (2)
C22—Fe1—C14—C1340.9 (4)C18—Fe1—C20—C19163.5 (5)
C23—Fe1—C14—C130.3 (3)C16—Fe1—C20—C19125.6 (3)
C18—Fe1—C14—C13115.9 (3)C21—Fe1—C20—C19119.9 (4)
C19—Fe1—C14—C1343.4 (3)C17—Fe1—C20—C19165.9 (2)
C20—Fe1—C14—C1377.7 (4)C19—C20—C21—C220.3 (4)
C16—Fe1—C14—C13163.0 (3)Fe1—C20—C21—C2259.1 (2)
C21—Fe1—C14—C1373.7 (7)C19—C20—C21—Fe159.3 (3)
C17—Fe1—C14—C13153.3 (3)C15—Fe1—C21—C2046.9 (4)
C18—C14—C15—C161.0 (3)C22—Fe1—C21—C20119.3 (4)
C13—C14—C15—C16173.5 (3)C14—Fe1—C21—C20160.3 (5)
Fe1—C14—C15—C1660.0 (2)C23—Fe1—C21—C2081.0 (3)
C18—C14—C15—Fe159.0 (2)C18—Fe1—C21—C20165.7 (2)
C13—C14—C15—Fe1113.5 (3)C19—Fe1—C21—C2037.1 (2)
C22—Fe1—C15—C16167.1 (6)C16—Fe1—C21—C2082.1 (3)
C14—Fe1—C15—C16119.1 (3)C17—Fe1—C21—C20125.0 (3)
C23—Fe1—C15—C16165.0 (3)C15—Fe1—C21—C22166.1 (3)
C18—Fe1—C15—C1680.7 (2)C14—Fe1—C21—C2241.1 (7)
C19—Fe1—C15—C16124.9 (3)C23—Fe1—C21—C2238.2 (3)
C20—Fe1—C15—C1683.1 (3)C18—Fe1—C21—C2275.0 (3)
C21—Fe1—C15—C1651.1 (4)C19—Fe1—C21—C2282.2 (3)
C17—Fe1—C15—C1637.3 (2)C20—Fe1—C21—C22119.3 (4)
C22—Fe1—C15—C1448.0 (7)C16—Fe1—C21—C22158.6 (3)
C23—Fe1—C15—C1475.9 (3)C17—Fe1—C21—C22115.7 (3)
C18—Fe1—C15—C1438.4 (2)C20—C21—C22—C230.6 (4)
C19—Fe1—C15—C14116.0 (2)Fe1—C21—C22—C2360.1 (3)
C20—Fe1—C15—C14157.8 (2)C20—C21—C22—Fe159.5 (3)
C16—Fe1—C15—C14119.1 (3)C15—Fe1—C22—C2335.1 (7)
C21—Fe1—C15—C14170.2 (3)C14—Fe1—C22—C2373.5 (3)
C17—Fe1—C15—C1481.8 (2)C18—Fe1—C22—C23116.3 (3)
C14—C15—C16—C170.6 (4)C19—Fe1—C22—C2337.8 (2)
Fe1—C15—C16—C1759.1 (2)C20—Fe1—C22—C2381.1 (3)
C14—C15—C16—Fe159.6 (2)C16—Fe1—C22—C23163.9 (4)
C22—Fe1—C16—C15172.8 (3)C21—Fe1—C22—C23118.3 (4)
C14—Fe1—C16—C1538.1 (2)C17—Fe1—C22—C23159.1 (3)
C23—Fe1—C16—C1546.8 (7)C15—Fe1—C22—C21153.3 (6)
C18—Fe1—C16—C1583.0 (2)C14—Fe1—C22—C21168.2 (2)
C19—Fe1—C16—C1574.1 (3)C23—Fe1—C22—C21118.3 (4)
C20—Fe1—C16—C15113.9 (2)C18—Fe1—C22—C21125.5 (2)
C21—Fe1—C16—C15155.4 (2)C19—Fe1—C22—C2180.5 (3)
C17—Fe1—C16—C15119.8 (3)C20—Fe1—C22—C2137.2 (2)
C15—Fe1—C16—C17119.8 (3)C16—Fe1—C22—C2145.6 (5)
C22—Fe1—C16—C1753.0 (5)C17—Fe1—C22—C2182.6 (3)
C14—Fe1—C16—C1781.6 (2)C20—C19—C23—C220.6 (4)
C23—Fe1—C16—C17166.6 (5)Fe1—C19—C23—C2259.5 (3)
C18—Fe1—C16—C1736.8 (2)C20—C19—C23—Fe160.1 (3)
C19—Fe1—C16—C17166.2 (2)C21—C22—C23—C190.7 (4)
C20—Fe1—C16—C17126.4 (2)Fe1—C22—C23—C1959.6 (3)
C21—Fe1—C16—C1784.9 (3)C21—C22—C23—Fe160.4 (2)
C15—C16—C17—C180.1 (4)C15—Fe1—C23—C1971.6 (3)
Fe1—C16—C17—C1858.4 (2)C22—Fe1—C23—C19118.8 (4)
C15—C16—C17—Fe158.5 (2)C14—Fe1—C23—C19114.1 (3)
C15—Fe1—C17—C1883.1 (2)C18—Fe1—C23—C19158.3 (2)
C22—Fe1—C17—C1884.0 (3)C20—Fe1—C23—C1937.5 (2)
C14—Fe1—C17—C1838.7 (2)C16—Fe1—C23—C1935.1 (7)
C23—Fe1—C17—C1850.4 (5)C21—Fe1—C23—C1980.7 (3)
C19—Fe1—C17—C18161.4 (5)C17—Fe1—C23—C19166.0 (3)
C20—Fe1—C17—C18167.0 (2)C15—Fe1—C23—C22169.6 (2)
C16—Fe1—C17—C18120.6 (3)C14—Fe1—C23—C22127.1 (2)
C21—Fe1—C17—C18126.6 (2)C18—Fe1—C23—C2282.9 (3)
C15—Fe1—C17—C1637.5 (2)C19—Fe1—C23—C22118.8 (4)
C22—Fe1—C17—C16155.5 (2)C20—Fe1—C23—C2281.3 (3)
C14—Fe1—C17—C1681.9 (2)C16—Fe1—C23—C22153.9 (5)
C23—Fe1—C17—C16171.0 (3)C21—Fe1—C23—C2238.1 (2)
C18—Fe1—C17—C16120.6 (3)C17—Fe1—C23—C2247.2 (5)

Experimental details

Crystal data
Chemical formula[Fe(C5H5)(C18H16N3O3)]
Mr443.28
Crystal system, space groupMonoclinic, P21/n
Temperature (K)294
a, b, c (Å)7.292 (2), 20.226 (5), 13.956 (4)
β (°) 93.669 (5)
V3)2054.2 (10)
Z4
Radiation typeMo Kα
µ (mm1)0.76
Crystal size (mm)0.24 × 0.22 × 0.18
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.826, 0.878
No. of measured, independent and
observed [I > 2σ(I)] reflections
11212, 4181, 2551
Rint0.054
(sin θ/λ)max1)0.628
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.049, 0.129, 0.99
No. of reflections4181
No. of parameters273
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.40, 0.53

Computer programs: SMART (Bruker,1998), SAINT (Bruker,1998), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2001), SHELXTL.

Selected geometric parameters (Å, º) top
O1—C11.216 (4)C1—C101.478 (4)
C1—C21.489 (4)C10—C131.332 (4)
O1—C1—C10120.2 (3)C13—C10—N1121.7 (3)
O1—C1—C2120.2 (3)C13—C10—C1121.7 (3)
C10—C1—C2119.5 (3)N1—C10—C1116.6 (3)
 

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