Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805038699/xu6063sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805038699/xu6063Isup2.hkl |
CCDC reference: 296708
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%).
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).
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.
Fig. 1. The molecular structure of (I), with 30% probability displacement ellipsoids (arbitrary spheres for H atoms). |
[Fe(C5H5)(C18H16N3O3)] | F(000) = 920 |
Mr = 443.28 | Dx = 1.433 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 2484 reflections |
a = 7.292 (2) Å | θ = 2.5–24.3° |
b = 20.226 (5) Å | µ = 0.76 mm−1 |
c = 13.956 (4) Å | T = 294 K |
β = 93.669 (5)° | Block, black |
V = 2054.2 (10) Å3 | 0.24 × 0.22 × 0.18 mm |
Z = 4 |
Bruker SMART CCD area-detector diffractometer | 4181 independent reflections |
Radiation source: fine-focus sealed tube | 2551 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.054 |
ϕ and ω scans | θmax = 26.5°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −8→9 |
Tmin = 0.826, Tmax = 0.878 | k = −22→25 |
11212 measured reflections | l = −11→17 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.129 | H-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 parameters | Δρmax = 0.40 e Å−3 |
0 restraints | Δρmin = −0.53 e Å−3 |
[Fe(C5H5)(C18H16N3O3)] | V = 2054.2 (10) Å3 |
Mr = 443.28 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 7.292 (2) Å | µ = 0.76 mm−1 |
b = 20.226 (5) Å | T = 294 K |
c = 13.956 (4) Å | 0.24 × 0.22 × 0.18 mm |
β = 93.669 (5)° |
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 = 0.878 | Rint = 0.054 |
11212 measured reflections |
R[F2 > 2σ(F2)] = 0.049 | 0 restraints |
wR(F2) = 0.129 | H-atom parameters constrained |
S = 0.99 | Δρmax = 0.40 e Å−3 |
4181 reflections | Δρmin = −0.53 e Å−3 |
273 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Fe1 | 0.22765 (6) | 1.01115 (2) | 0.29240 (4) | 0.03427 (18) | |
O1 | 0.5728 (3) | 0.83702 (11) | 0.5326 (2) | 0.0584 (8) | |
O2 | 0.1496 (3) | 0.76394 (11) | 0.61889 (17) | 0.0489 (6) | |
O3 | 0.6221 (3) | 0.57989 (11) | 0.47810 (19) | 0.0522 (7) | |
N1 | 0.1376 (3) | 0.81187 (12) | 0.40552 (19) | 0.0315 (6) | |
N2 | 0.1749 (4) | 0.77970 (14) | 0.3239 (2) | 0.0469 (8) | |
N3 | −0.1227 (4) | 0.76715 (16) | 0.3551 (2) | 0.0562 (9) | |
C1 | 0.4268 (4) | 0.81071 (15) | 0.5090 (2) | 0.0346 (8) | |
C2 | 0.3994 (4) | 0.73906 (15) | 0.5280 (2) | 0.0305 (7) | |
C3 | 0.5257 (4) | 0.69431 (16) | 0.4930 (2) | 0.0324 (8) | |
H3 | 0.6198 | 0.7095 | 0.4568 | 0.039* | |
C4 | 0.5103 (4) | 0.62812 (17) | 0.5122 (2) | 0.0378 (9) | |
C5 | 0.3701 (5) | 0.60550 (17) | 0.5664 (3) | 0.0439 (9) | |
H5 | 0.3588 | 0.5605 | 0.5781 | 0.053* | |
C6 | 0.2472 (4) | 0.64926 (17) | 0.6030 (2) | 0.0438 (9) | |
H6 | 0.1559 | 0.6338 | 0.6408 | 0.053* | |
C7 | 0.2600 (4) | 0.71656 (16) | 0.5834 (2) | 0.0348 (8) | |
C8 | 0.0054 (5) | 0.7428 (2) | 0.6765 (3) | 0.0601 (11) | |
H8A | −0.0777 | 0.7147 | 0.6392 | 0.090* | |
H8B | −0.0598 | 0.7807 | 0.6980 | 0.090* | |
H8C | 0.0570 | 0.7188 | 0.7312 | 0.090* | |
C9 | 0.7755 (5) | 0.60015 (18) | 0.4297 (3) | 0.0624 (12) | |
H9A | 0.7352 | 0.6246 | 0.3733 | 0.094* | |
H9B | 0.8435 | 0.5620 | 0.4116 | 0.094* | |
H9C | 0.8527 | 0.6277 | 0.4712 | 0.094* | |
C10 | 0.2776 (4) | 0.84912 (15) | 0.4585 (2) | 0.0299 (7) | |
C11 | −0.0398 (4) | 0.80330 (16) | 0.4223 (3) | 0.0445 (9) | |
H11 | −0.0961 | 0.8207 | 0.4746 | 0.053* | |
C12 | 0.0140 (6) | 0.75470 (19) | 0.2965 (3) | 0.0555 (11) | |
H12 | −0.0048 | 0.7301 | 0.2405 | 0.067* | |
C13 | 0.2768 (4) | 0.91498 (15) | 0.4592 (2) | 0.0328 (8) | |
H13 | 0.3703 | 0.9346 | 0.4978 | 0.039* | |
C14 | 0.1516 (4) | 0.96037 (16) | 0.4088 (2) | 0.0334 (8) | |
C15 | 0.0244 (4) | 0.94979 (17) | 0.3284 (3) | 0.0420 (9) | |
H15 | −0.0041 | 0.9092 | 0.2998 | 0.050* | |
C16 | −0.0507 (5) | 1.01155 (19) | 0.2996 (3) | 0.0523 (10) | |
H16 | −0.1380 | 1.0187 | 0.2491 | 0.063* | |
C17 | 0.0299 (5) | 1.06069 (18) | 0.3608 (3) | 0.0525 (11) | |
H17 | 0.0042 | 1.1057 | 0.3573 | 0.063* | |
C18 | 0.1552 (5) | 1.03047 (16) | 0.4276 (3) | 0.0434 (9) | |
H18 | 0.2275 | 1.0518 | 0.4754 | 0.052* | |
C19 | 0.3665 (6) | 0.9642 (2) | 0.1908 (3) | 0.0606 (11) | |
H19 | 0.3482 | 0.9207 | 0.1709 | 0.073* | |
C20 | 0.2777 (5) | 1.0194 (2) | 0.1511 (3) | 0.0542 (10) | |
H20 | 0.1898 | 1.0191 | 0.0998 | 0.065* | |
C21 | 0.3416 (5) | 1.0753 (2) | 0.2004 (3) | 0.0545 (11) | |
H21 | 0.3045 | 1.1186 | 0.1879 | 0.065* | |
C22 | 0.4726 (5) | 1.0548 (2) | 0.2728 (3) | 0.0609 (12) | |
H22 | 0.5366 | 1.0820 | 0.3170 | 0.073* | |
C23 | 0.4890 (5) | 0.9857 (2) | 0.2663 (3) | 0.0636 (12) | |
H23 | 0.5668 | 0.9590 | 0.3049 | 0.076* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Fe1 | 0.0211 (3) | 0.0380 (3) | 0.0451 (3) | −0.0006 (2) | 0.0126 (2) | 0.0024 (2) |
O1 | 0.0296 (13) | 0.0420 (15) | 0.102 (2) | −0.0102 (12) | −0.0110 (14) | −0.0016 (14) |
O2 | 0.0420 (15) | 0.0492 (15) | 0.0581 (16) | 0.0013 (12) | 0.0243 (13) | 0.0026 (12) |
O3 | 0.0454 (15) | 0.0387 (14) | 0.0743 (19) | 0.0054 (11) | 0.0180 (14) | 0.0042 (13) |
N1 | 0.0248 (14) | 0.0321 (15) | 0.0378 (16) | −0.0040 (11) | 0.0035 (12) | −0.0004 (12) |
N2 | 0.0438 (19) | 0.0548 (19) | 0.0415 (18) | 0.0041 (15) | −0.0026 (15) | −0.0107 (15) |
N3 | 0.045 (2) | 0.055 (2) | 0.067 (2) | −0.0186 (16) | −0.0106 (19) | 0.0046 (18) |
C1 | 0.0287 (17) | 0.0350 (18) | 0.041 (2) | −0.0030 (15) | 0.0082 (15) | −0.0001 (15) |
C2 | 0.0233 (16) | 0.0344 (18) | 0.0335 (18) | −0.0028 (13) | −0.0012 (14) | 0.0013 (15) |
C3 | 0.0203 (17) | 0.039 (2) | 0.038 (2) | −0.0042 (13) | 0.0042 (15) | 0.0042 (15) |
C4 | 0.0335 (19) | 0.037 (2) | 0.043 (2) | 0.0004 (15) | 0.0010 (17) | 0.0024 (16) |
C5 | 0.045 (2) | 0.038 (2) | 0.049 (2) | −0.0015 (16) | 0.0112 (18) | 0.0117 (17) |
C6 | 0.034 (2) | 0.049 (2) | 0.049 (2) | −0.0057 (16) | 0.0097 (17) | 0.0145 (18) |
C7 | 0.0285 (18) | 0.042 (2) | 0.0337 (19) | −0.0016 (15) | 0.0035 (15) | 0.0039 (16) |
C8 | 0.046 (2) | 0.068 (3) | 0.071 (3) | 0.0032 (19) | 0.034 (2) | 0.008 (2) |
C9 | 0.054 (3) | 0.057 (3) | 0.079 (3) | 0.004 (2) | 0.031 (2) | −0.004 (2) |
C10 | 0.0239 (16) | 0.0301 (18) | 0.0366 (19) | −0.0069 (13) | 0.0080 (14) | −0.0011 (15) |
C11 | 0.0278 (18) | 0.048 (2) | 0.058 (3) | −0.0104 (16) | 0.0080 (18) | 0.0020 (19) |
C12 | 0.060 (3) | 0.052 (2) | 0.052 (3) | 0.001 (2) | −0.017 (2) | −0.012 (2) |
C13 | 0.0261 (17) | 0.037 (2) | 0.0359 (19) | −0.0094 (14) | 0.0069 (15) | −0.0007 (15) |
C14 | 0.0268 (17) | 0.0325 (18) | 0.043 (2) | −0.0020 (14) | 0.0151 (16) | 0.0028 (16) |
C15 | 0.0201 (17) | 0.045 (2) | 0.061 (2) | −0.0079 (15) | 0.0049 (17) | 0.0066 (18) |
C16 | 0.0211 (17) | 0.065 (3) | 0.072 (3) | 0.0053 (18) | 0.0120 (18) | 0.023 (2) |
C17 | 0.046 (2) | 0.043 (2) | 0.073 (3) | 0.0144 (19) | 0.034 (2) | 0.009 (2) |
C18 | 0.043 (2) | 0.039 (2) | 0.051 (2) | −0.0009 (16) | 0.0240 (18) | −0.0007 (17) |
C19 | 0.045 (2) | 0.067 (3) | 0.073 (3) | 0.004 (2) | 0.027 (2) | −0.019 (2) |
C20 | 0.040 (2) | 0.083 (3) | 0.041 (2) | −0.002 (2) | 0.0126 (18) | 0.002 (2) |
C21 | 0.047 (2) | 0.055 (3) | 0.064 (3) | −0.0104 (19) | 0.022 (2) | 0.014 (2) |
C22 | 0.038 (2) | 0.091 (4) | 0.055 (3) | −0.026 (2) | 0.018 (2) | −0.009 (2) |
C23 | 0.025 (2) | 0.098 (4) | 0.070 (3) | 0.017 (2) | 0.018 (2) | 0.020 (3) |
Fe1—C15 | 2.021 (3) | C6—H6 | 0.9300 |
Fe1—C22 | 2.026 (4) | C8—H8A | 0.9600 |
Fe1—C14 | 2.029 (3) | C8—H8B | 0.9600 |
Fe1—C23 | 2.030 (4) | C8—H8C | 0.9600 |
Fe1—C18 | 2.030 (4) | C9—H9A | 0.9600 |
Fe1—C19 | 2.031 (4) | C9—H9B | 0.9600 |
Fe1—C20 | 2.036 (4) | C9—H9C | 0.9600 |
Fe1—C16 | 2.039 (3) | C10—C13 | 1.332 (4) |
Fe1—C21 | 2.039 (4) | C11—H11 | 0.9300 |
Fe1—C17 | 2.042 (3) | C12—H12 | 0.9300 |
O1—C1 | 1.216 (4) | C13—C14 | 1.445 (4) |
O2—C7 | 1.365 (4) | C13—H13 | 0.9300 |
O2—C8 | 1.430 (4) | C14—C15 | 1.426 (4) |
O3—C4 | 1.376 (4) | C14—C18 | 1.442 (5) |
O3—C9 | 1.405 (4) | C15—C16 | 1.412 (5) |
N1—C11 | 1.340 (4) | C15—H15 | 0.9300 |
N1—N2 | 1.354 (4) | C16—C17 | 1.414 (5) |
N1—C10 | 1.436 (4) | C16—H16 | 0.9300 |
N2—C12 | 1.312 (4) | C17—C18 | 1.403 (5) |
N3—C11 | 1.307 (4) | C17—H17 | 0.9300 |
N3—C12 | 1.353 (5) | C18—H18 | 0.9300 |
C1—C2 | 1.489 (4) | C19—C20 | 1.389 (5) |
C1—C10 | 1.478 (4) | C19—C23 | 1.406 (6) |
C2—C7 | 1.393 (4) | C19—H19 | 0.9300 |
C2—C3 | 1.401 (4) | C20—C21 | 1.388 (5) |
C3—C4 | 1.371 (4) | C20—H20 | 0.9300 |
C3—H3 | 0.9300 | C21—C22 | 1.407 (5) |
C4—C5 | 1.387 (4) | C21—H21 | 0.9300 |
C5—C6 | 1.381 (5) | C22—C23 | 1.407 (6) |
C5—H5 | 0.9300 | C22—H22 | 0.9300 |
C6—C7 | 1.392 (4) | C23—H23 | 0.9300 |
C15—Fe1—C22 | 165.40 (17) | O3—C9—H9A | 109.5 |
C15—Fe1—C14 | 41.22 (13) | O3—C9—H9B | 109.5 |
C22—Fe1—C14 | 128.08 (16) | H9A—C9—H9B | 109.5 |
C15—Fe1—C23 | 126.92 (17) | O3—C9—H9C | 109.5 |
C22—Fe1—C23 | 40.59 (16) | H9A—C9—H9C | 109.5 |
C14—Fe1—C23 | 108.86 (15) | H9B—C9—H9C | 109.5 |
C15—Fe1—C18 | 69.44 (15) | C13—C10—N1 | 121.7 (3) |
C22—Fe1—C18 | 108.98 (16) | C13—C10—C1 | 121.7 (3) |
C14—Fe1—C18 | 41.62 (13) | N1—C10—C1 | 116.6 (3) |
C23—Fe1—C18 | 121.27 (17) | N3—C11—N1 | 110.8 (3) |
C15—Fe1—C19 | 107.02 (16) | N3—C11—H11 | 124.6 |
C22—Fe1—C19 | 68.07 (17) | N1—C11—H11 | 124.6 |
C14—Fe1—C19 | 119.76 (16) | N2—C12—N3 | 115.6 (3) |
C23—Fe1—C19 | 40.51 (16) | N2—C12—H12 | 122.2 |
C18—Fe1—C19 | 155.57 (17) | N3—C12—H12 | 122.2 |
C15—Fe1—C20 | 118.10 (16) | C10—C13—C14 | 129.4 (3) |
C22—Fe1—C20 | 67.63 (16) | C10—C13—H13 | 115.3 |
C14—Fe1—C20 | 153.19 (15) | C14—C13—H13 | 115.3 |
C23—Fe1—C20 | 67.54 (16) | C15—C14—C18 | 107.1 (3) |
C18—Fe1—C20 | 163.42 (15) | C15—C14—C13 | 130.3 (3) |
C19—Fe1—C20 | 39.95 (16) | C18—C14—C13 | 122.1 (3) |
C15—Fe1—C16 | 40.71 (13) | C15—C14—Fe1 | 69.10 (18) |
C22—Fe1—C16 | 153.36 (18) | C18—C14—Fe1 | 69.23 (18) |
C14—Fe1—C16 | 68.82 (14) | C13—C14—Fe1 | 121.0 (2) |
C23—Fe1—C16 | 163.55 (18) | C16—C15—C14 | 108.2 (3) |
C18—Fe1—C16 | 68.56 (16) | C16—C15—Fe1 | 70.32 (19) |
C19—Fe1—C16 | 125.36 (18) | C14—C15—Fe1 | 69.68 (18) |
C20—Fe1—C16 | 106.74 (17) | C16—C15—H15 | 125.9 |
C15—Fe1—C21 | 151.89 (16) | C14—C15—H15 | 125.9 |
C22—Fe1—C21 | 40.51 (15) | Fe1—C15—H15 | 125.7 |
C14—Fe1—C21 | 165.79 (16) | C15—C16—C17 | 108.1 (3) |
C23—Fe1—C21 | 67.84 (17) | C15—C16—Fe1 | 68.98 (18) |
C18—Fe1—C21 | 127.13 (15) | C17—C16—Fe1 | 69.9 (2) |
C19—Fe1—C21 | 67.43 (18) | C15—C16—H16 | 125.9 |
C20—Fe1—C21 | 39.83 (15) | C17—C16—H16 | 125.9 |
C16—Fe1—C21 | 118.41 (16) | Fe1—C16—H16 | 126.8 |
C15—Fe1—C17 | 68.55 (15) | C18—C17—C16 | 108.9 (3) |
C22—Fe1—C17 | 120.26 (18) | C18—C17—Fe1 | 69.4 (2) |
C14—Fe1—C17 | 68.72 (14) | C16—C17—Fe1 | 69.6 (2) |
C23—Fe1—C17 | 155.20 (19) | C18—C17—H17 | 125.6 |
C18—Fe1—C17 | 40.32 (14) | C16—C17—H17 | 125.6 |
C19—Fe1—C17 | 162.67 (18) | Fe1—C17—H17 | 127.0 |
C20—Fe1—C17 | 126.03 (16) | C17—C18—C14 | 107.7 (3) |
C16—Fe1—C17 | 40.54 (15) | C17—C18—Fe1 | 70.3 (2) |
C21—Fe1—C17 | 108.10 (16) | C14—C18—Fe1 | 69.14 (18) |
C7—O2—C8 | 117.8 (3) | C17—C18—H18 | 126.2 |
C4—O3—C9 | 117.9 (3) | C14—C18—H18 | 126.2 |
C11—N1—N2 | 109.5 (3) | Fe1—C18—H18 | 126.0 |
C11—N1—C10 | 129.8 (3) | C20—C19—C23 | 107.9 (4) |
N2—N1—C10 | 120.7 (3) | C20—C19—Fe1 | 70.2 (2) |
C12—N2—N1 | 101.9 (3) | C23—C19—Fe1 | 69.7 (2) |
C11—N3—C12 | 102.3 (3) | C20—C19—H19 | 126.0 |
O1—C1—C10 | 120.2 (3) | C23—C19—H19 | 126.0 |
O1—C1—C2 | 120.2 (3) | Fe1—C19—H19 | 125.6 |
C10—C1—C2 | 119.5 (3) | C21—C20—C19 | 108.9 (4) |
C7—C2—C3 | 120.1 (3) | C21—C20—Fe1 | 70.2 (2) |
C7—C2—C1 | 121.9 (3) | C19—C20—Fe1 | 69.8 (2) |
C3—C2—C1 | 117.9 (3) | C21—C20—H20 | 125.6 |
C4—C3—C2 | 119.9 (3) | C19—C20—H20 | 125.6 |
C4—C3—H3 | 120.1 | Fe1—C20—H20 | 126.0 |
C2—C3—H3 | 120.1 | C20—C21—C22 | 108.0 (4) |
C3—C4—O3 | 124.5 (3) | C20—C21—Fe1 | 70.0 (2) |
C3—C4—C5 | 120.1 (3) | C22—C21—Fe1 | 69.3 (2) |
O3—C4—C5 | 115.4 (3) | C20—C21—H21 | 126.0 |
C6—C5—C4 | 120.6 (3) | C22—C21—H21 | 126.0 |
C6—C5—H5 | 119.7 | Fe1—C21—H21 | 126.3 |
C4—C5—H5 | 119.7 | C23—C22—C21 | 107.6 (4) |
C5—C6—C7 | 120.0 (3) | C23—C22—Fe1 | 69.8 (2) |
C5—C6—H6 | 120.0 | C21—C22—Fe1 | 70.2 (2) |
C7—C6—H6 | 120.0 | C23—C22—H22 | 126.2 |
O2—C7—C2 | 116.1 (3) | C21—C22—H22 | 126.2 |
O2—C7—C6 | 124.5 (3) | Fe1—C22—H22 | 125.3 |
C2—C7—C6 | 119.3 (3) | C19—C23—C22 | 107.7 (4) |
O2—C8—H8A | 109.5 | C19—C23—Fe1 | 69.8 (2) |
O2—C8—H8B | 109.5 | C22—C23—Fe1 | 69.6 (2) |
H8A—C8—H8B | 109.5 | C19—C23—H23 | 126.2 |
O2—C8—H8C | 109.5 | C22—C23—H23 | 126.2 |
H8A—C8—H8C | 109.5 | Fe1—C23—H23 | 126.0 |
H8B—C8—H8C | 109.5 | ||
C11—N1—N2—C12 | 1.0 (4) | C19—Fe1—C17—C16 | 40.8 (6) |
C10—N1—N2—C12 | −177.7 (3) | C20—Fe1—C17—C16 | 72.4 (3) |
O1—C1—C2—C7 | 121.6 (4) | C21—Fe1—C17—C16 | 112.8 (2) |
C10—C1—C2—C7 | −60.4 (4) | C16—C17—C18—C14 | −0.7 (4) |
O1—C1—C2—C3 | −54.7 (5) | Fe1—C17—C18—C14 | −59.3 (2) |
C10—C1—C2—C3 | 123.3 (3) | C16—C17—C18—Fe1 | 58.5 (2) |
C7—C2—C3—C4 | 0.9 (5) | C15—C14—C18—C17 | 1.1 (3) |
C1—C2—C3—C4 | 177.3 (3) | C13—C14—C18—C17 | 174.3 (3) |
C2—C3—C4—O3 | 177.2 (3) | Fe1—C14—C18—C17 | 60.0 (2) |
C2—C3—C4—C5 | −0.1 (5) | C15—C14—C18—Fe1 | −58.9 (2) |
C9—O3—C4—C3 | 7.8 (5) | C13—C14—C18—Fe1 | 114.3 (3) |
C9—O3—C4—C5 | −174.8 (3) | C15—Fe1—C18—C17 | −80.7 (2) |
C3—C4—C5—C6 | −1.3 (5) | C22—Fe1—C18—C17 | 114.7 (3) |
O3—C4—C5—C6 | −178.8 (3) | C14—Fe1—C18—C17 | −118.8 (3) |
C4—C5—C6—C7 | 1.9 (5) | C23—Fe1—C18—C17 | 157.8 (2) |
C8—O2—C7—C2 | −179.7 (3) | C19—Fe1—C18—C17 | −166.7 (4) |
C8—O2—C7—C6 | −3.0 (5) | C20—Fe1—C18—C17 | 39.5 (6) |
C3—C2—C7—O2 | 176.5 (3) | C16—Fe1—C18—C17 | −37.0 (2) |
C1—C2—C7—O2 | 0.3 (5) | C21—Fe1—C18—C17 | 73.1 (3) |
C3—C2—C7—C6 | −0.4 (5) | C15—Fe1—C18—C14 | 38.07 (18) |
C1—C2—C7—C6 | −176.6 (3) | C22—Fe1—C18—C14 | −126.5 (2) |
C5—C6—C7—O2 | −177.6 (3) | C23—Fe1—C18—C14 | −83.4 (2) |
C5—C6—C7—C2 | −1.0 (5) | C19—Fe1—C18—C14 | −47.9 (4) |
C11—N1—C10—C13 | −70.9 (4) | C20—Fe1—C18—C14 | 158.3 (5) |
N2—N1—C10—C13 | 107.5 (3) | C16—Fe1—C18—C14 | 81.8 (2) |
C11—N1—C10—C1 | 111.5 (4) | C21—Fe1—C18—C14 | −168.1 (2) |
N2—N1—C10—C1 | −70.1 (4) | C17—Fe1—C18—C14 | 118.8 (3) |
O1—C1—C10—C13 | −17.8 (5) | C15—Fe1—C19—C20 | 113.7 (3) |
C2—C1—C10—C13 | 164.1 (3) | C22—Fe1—C19—C20 | −80.9 (3) |
O1—C1—C10—N1 | 159.8 (3) | C14—Fe1—C19—C20 | 156.7 (2) |
C2—C1—C10—N1 | −18.3 (4) | C23—Fe1—C19—C20 | −118.8 (4) |
C12—N3—C11—N1 | −0.4 (4) | C18—Fe1—C19—C20 | −168.7 (3) |
N2—N1—C11—N3 | −0.4 (4) | C16—Fe1—C19—C20 | 72.7 (3) |
C10—N1—C11—N3 | 178.2 (3) | C21—Fe1—C19—C20 | −37.0 (2) |
N1—N2—C12—N3 | −1.3 (4) | C17—Fe1—C19—C20 | 41.3 (6) |
C11—N3—C12—N2 | 1.1 (5) | C15—Fe1—C19—C23 | −127.5 (3) |
N1—C10—C13—C14 | −2.6 (5) | C22—Fe1—C19—C23 | 37.9 (2) |
C1—C10—C13—C14 | 174.9 (3) | C14—Fe1—C19—C23 | −84.5 (3) |
C10—C13—C14—C15 | −17.1 (5) | C18—Fe1—C19—C23 | −49.9 (5) |
C10—C13—C14—C18 | 171.3 (3) | C20—Fe1—C19—C23 | 118.8 (4) |
C10—C13—C14—Fe1 | −105.0 (3) | C16—Fe1—C19—C23 | −168.5 (2) |
C22—Fe1—C14—C15 | −166.2 (2) | C21—Fe1—C19—C23 | 81.8 (3) |
C23—Fe1—C14—C15 | −125.0 (2) | C17—Fe1—C19—C23 | 160.1 (5) |
C18—Fe1—C14—C15 | 118.8 (3) | C23—C19—C20—C21 | −0.2 (4) |
C19—Fe1—C14—C15 | −81.9 (2) | Fe1—C19—C20—C21 | 59.5 (3) |
C20—Fe1—C14—C15 | −47.6 (4) | C23—C19—C20—Fe1 | −59.7 (3) |
C16—Fe1—C14—C15 | 37.7 (2) | C15—Fe1—C20—C21 | 157.1 (2) |
C21—Fe1—C14—C15 | 160.9 (6) | C22—Fe1—C20—C21 | −37.8 (2) |
C17—Fe1—C14—C15 | 81.3 (2) | C14—Fe1—C20—C21 | −169.4 (3) |
C15—Fe1—C14—C18 | −118.8 (3) | C23—Fe1—C20—C21 | −81.9 (3) |
C22—Fe1—C14—C18 | 74.9 (3) | C18—Fe1—C20—C21 | 43.6 (6) |
C23—Fe1—C14—C18 | 116.2 (2) | C19—Fe1—C20—C21 | −119.9 (4) |
C19—Fe1—C14—C18 | 159.3 (2) | C16—Fe1—C20—C21 | 114.5 (3) |
C20—Fe1—C14—C18 | −166.5 (3) | C17—Fe1—C20—C21 | 74.2 (3) |
C16—Fe1—C14—C18 | −81.1 (2) | C15—Fe1—C20—C19 | −83.1 (3) |
C21—Fe1—C14—C18 | 42.1 (6) | C22—Fe1—C20—C19 | 82.1 (3) |
C17—Fe1—C14—C18 | −37.5 (2) | C14—Fe1—C20—C19 | −49.6 (4) |
C15—Fe1—C14—C13 | 125.3 (4) | C23—Fe1—C20—C19 | 38.0 (2) |
C22—Fe1—C14—C13 | −40.9 (4) | C18—Fe1—C20—C19 | 163.5 (5) |
C23—Fe1—C14—C13 | 0.3 (3) | C16—Fe1—C20—C19 | −125.6 (3) |
C18—Fe1—C14—C13 | −115.9 (3) | C21—Fe1—C20—C19 | 119.9 (4) |
C19—Fe1—C14—C13 | 43.4 (3) | C17—Fe1—C20—C19 | −165.9 (2) |
C20—Fe1—C14—C13 | 77.7 (4) | C19—C20—C21—C22 | −0.3 (4) |
C16—Fe1—C14—C13 | 163.0 (3) | Fe1—C20—C21—C22 | 59.1 (2) |
C21—Fe1—C14—C13 | −73.7 (7) | C19—C20—C21—Fe1 | −59.3 (3) |
C17—Fe1—C14—C13 | −153.3 (3) | C15—Fe1—C21—C20 | −46.9 (4) |
C18—C14—C15—C16 | −1.0 (3) | C22—Fe1—C21—C20 | 119.3 (4) |
C13—C14—C15—C16 | −173.5 (3) | C14—Fe1—C21—C20 | 160.3 (5) |
Fe1—C14—C15—C16 | −60.0 (2) | C23—Fe1—C21—C20 | 81.0 (3) |
C18—C14—C15—Fe1 | 59.0 (2) | C18—Fe1—C21—C20 | −165.7 (2) |
C13—C14—C15—Fe1 | −113.5 (3) | C19—Fe1—C21—C20 | 37.1 (2) |
C22—Fe1—C15—C16 | 167.1 (6) | C16—Fe1—C21—C20 | −82.1 (3) |
C14—Fe1—C15—C16 | 119.1 (3) | C17—Fe1—C21—C20 | −125.0 (3) |
C23—Fe1—C15—C16 | −165.0 (3) | C15—Fe1—C21—C22 | −166.1 (3) |
C18—Fe1—C15—C16 | 80.7 (2) | C14—Fe1—C21—C22 | 41.1 (7) |
C19—Fe1—C15—C16 | −124.9 (3) | C23—Fe1—C21—C22 | −38.2 (3) |
C20—Fe1—C15—C16 | −83.1 (3) | C18—Fe1—C21—C22 | 75.0 (3) |
C21—Fe1—C15—C16 | −51.1 (4) | C19—Fe1—C21—C22 | −82.2 (3) |
C17—Fe1—C15—C16 | 37.3 (2) | C20—Fe1—C21—C22 | −119.3 (4) |
C22—Fe1—C15—C14 | 48.0 (7) | C16—Fe1—C21—C22 | 158.6 (3) |
C23—Fe1—C15—C14 | 75.9 (3) | C17—Fe1—C21—C22 | 115.7 (3) |
C18—Fe1—C15—C14 | −38.4 (2) | C20—C21—C22—C23 | 0.6 (4) |
C19—Fe1—C15—C14 | 116.0 (2) | Fe1—C21—C22—C23 | 60.1 (3) |
C20—Fe1—C15—C14 | 157.8 (2) | C20—C21—C22—Fe1 | −59.5 (3) |
C16—Fe1—C15—C14 | −119.1 (3) | C15—Fe1—C22—C23 | 35.1 (7) |
C21—Fe1—C15—C14 | −170.2 (3) | C14—Fe1—C22—C23 | 73.5 (3) |
C17—Fe1—C15—C14 | −81.8 (2) | C18—Fe1—C22—C23 | 116.3 (3) |
C14—C15—C16—C17 | 0.6 (4) | C19—Fe1—C22—C23 | −37.8 (2) |
Fe1—C15—C16—C17 | −59.1 (2) | C20—Fe1—C22—C23 | −81.1 (3) |
C14—C15—C16—Fe1 | 59.6 (2) | C16—Fe1—C22—C23 | −163.9 (4) |
C22—Fe1—C16—C15 | −172.8 (3) | C21—Fe1—C22—C23 | −118.3 (4) |
C14—Fe1—C16—C15 | −38.1 (2) | C17—Fe1—C22—C23 | 159.1 (3) |
C23—Fe1—C16—C15 | 46.8 (7) | C15—Fe1—C22—C21 | 153.3 (6) |
C18—Fe1—C16—C15 | −83.0 (2) | C14—Fe1—C22—C21 | −168.2 (2) |
C19—Fe1—C16—C15 | 74.1 (3) | C23—Fe1—C22—C21 | 118.3 (4) |
C20—Fe1—C16—C15 | 113.9 (2) | C18—Fe1—C22—C21 | −125.5 (2) |
C21—Fe1—C16—C15 | 155.4 (2) | C19—Fe1—C22—C21 | 80.5 (3) |
C17—Fe1—C16—C15 | −119.8 (3) | C20—Fe1—C22—C21 | 37.2 (2) |
C15—Fe1—C16—C17 | 119.8 (3) | C16—Fe1—C22—C21 | −45.6 (5) |
C22—Fe1—C16—C17 | −53.0 (5) | C17—Fe1—C22—C21 | −82.6 (3) |
C14—Fe1—C16—C17 | 81.6 (2) | C20—C19—C23—C22 | 0.6 (4) |
C23—Fe1—C16—C17 | 166.6 (5) | Fe1—C19—C23—C22 | −59.5 (3) |
C18—Fe1—C16—C17 | 36.8 (2) | C20—C19—C23—Fe1 | 60.1 (3) |
C19—Fe1—C16—C17 | −166.2 (2) | C21—C22—C23—C19 | −0.7 (4) |
C20—Fe1—C16—C17 | −126.4 (2) | Fe1—C22—C23—C19 | 59.6 (3) |
C21—Fe1—C16—C17 | −84.9 (3) | C21—C22—C23—Fe1 | −60.4 (2) |
C15—C16—C17—C18 | 0.1 (4) | C15—Fe1—C23—C19 | 71.6 (3) |
Fe1—C16—C17—C18 | −58.4 (2) | C22—Fe1—C23—C19 | −118.8 (4) |
C15—C16—C17—Fe1 | 58.5 (2) | C14—Fe1—C23—C19 | 114.1 (3) |
C15—Fe1—C17—C18 | 83.1 (2) | C18—Fe1—C23—C19 | 158.3 (2) |
C22—Fe1—C17—C18 | −84.0 (3) | C20—Fe1—C23—C19 | −37.5 (2) |
C14—Fe1—C17—C18 | 38.7 (2) | C16—Fe1—C23—C19 | 35.1 (7) |
C23—Fe1—C17—C18 | −50.4 (5) | C21—Fe1—C23—C19 | −80.7 (3) |
C19—Fe1—C17—C18 | 161.4 (5) | C17—Fe1—C23—C19 | −166.0 (3) |
C20—Fe1—C17—C18 | −167.0 (2) | C15—Fe1—C23—C22 | −169.6 (2) |
C16—Fe1—C17—C18 | 120.6 (3) | C14—Fe1—C23—C22 | −127.1 (2) |
C21—Fe1—C17—C18 | −126.6 (2) | C18—Fe1—C23—C22 | −82.9 (3) |
C15—Fe1—C17—C16 | −37.5 (2) | C19—Fe1—C23—C22 | 118.8 (4) |
C22—Fe1—C17—C16 | 155.5 (2) | C20—Fe1—C23—C22 | 81.3 (3) |
C14—Fe1—C17—C16 | −81.9 (2) | C16—Fe1—C23—C22 | 153.9 (5) |
C23—Fe1—C17—C16 | −171.0 (3) | C21—Fe1—C23—C22 | 38.1 (2) |
C18—Fe1—C17—C16 | −120.6 (3) | C17—Fe1—C23—C22 | −47.2 (5) |
Experimental details
Crystal data | |
Chemical formula | [Fe(C5H5)(C18H16N3O3)] |
Mr | 443.28 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 294 |
a, b, c (Å) | 7.292 (2), 20.226 (5), 13.956 (4) |
β (°) | 93.669 (5) |
V (Å3) | 2054.2 (10) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.76 |
Crystal size (mm) | 0.24 × 0.22 × 0.18 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.826, 0.878 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11212, 4181, 2551 |
Rint | 0.054 |
(sin θ/λ)max (Å−1) | 0.628 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.049, 0.129, 0.99 |
No. of reflections | 4181 |
No. of parameters | 273 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.40, −0.53 |
Computer programs: SMART (Bruker,1998), SAINT (Bruker,1998), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2001), SHELXTL.
O1—C1 | 1.216 (4) | C1—C10 | 1.478 (4) |
C1—C2 | 1.489 (4) | C10—C13 | 1.332 (4) |
O1—C1—C10 | 120.2 (3) | C13—C10—N1 | 121.7 (3) |
O1—C1—C2 | 120.2 (3) | C13—C10—C1 | 121.7 (3) |
C10—C1—C2 | 119.5 (3) | N1—C10—C1 | 116.6 (3) |
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.