Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805030242/br6218sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805030242/br6218Isup2.hkl |
CCDC reference: 287457
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (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
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, C═O), 1599 (vs, C═N).
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).
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.
[Fe(C5H5)(C10H13N2O2] | F(000) = 1312 |
Mr = 314.16 | Dx = 1.454 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 36.770 (7) Å | Cell parameters from 25 reflections |
b = 7.6040 (15) Å | θ = 10–13° |
c = 10.366 (2) Å | µ = 1.05 mm−1 |
β = 97.82 (3)° | T = 295 K |
V = 2871.4 (10) Å3 | Block, orange |
Z = 8 | 0.40 × 0.20 × 0.20 mm |
Enraf–Nonius CAD4 diffractometer | 2178 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.039 |
Graphite monochromator | θmax = 26.0°, θmin = 1.1° |
ω/2θ scans | h = 0→45 |
Absorption correction: empirical (using intensity measurements) via ψ scan (North et al., 1968) | k = 0→9 |
Tmin = 0.747, Tmax = 0.803 | l = −12→12 |
2848 measured reflections | 3 standard reflections every 200 reflections |
2804 independent reflections | intensity decay: none |
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)] = 0.060 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.184 | H-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 parameters | Δρmax = 1.46 e Å−3 |
13 restraints | Δρmin = −0.76 e Å−3 |
[Fe(C5H5)(C10H13N2O2] | V = 2871.4 (10) Å3 |
Mr = 314.16 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 36.770 (7) Å | µ = 1.05 mm−1 |
b = 7.6040 (15) Å | T = 295 K |
c = 10.366 (2) Å | 0.40 × 0.20 × 0.20 mm |
β = 97.82 (3)° |
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 = 0.803 | 3 standard reflections every 200 reflections |
2848 measured reflections | intensity decay: none |
2804 independent reflections |
R[F2 > 2σ(F2)] = 0.060 | 13 restraints |
wR(F2) = 0.184 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.098P)2 + 11.3526P] where P = (Fo2 + 2Fc2)/3 |
2804 reflections | Δρmax = 1.46 e Å−3 |
177 parameters | Δρmin = −0.76 e Å−3 |
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 | ||
Fe | 0.071355 (18) | 0.23531 (8) | 0.20163 (6) | 0.0358 (3) | |
O1 | 0.18707 (10) | 0.3121 (6) | 0.7058 (3) | 0.0544 (9) | |
O2 | 0.24378 (11) | 0.3154 (8) | 0.6509 (4) | 0.0729 (13) | |
N1 | 0.19646 (11) | 0.2243 (6) | 0.5067 (4) | 0.0469 (10) | |
H1N | 0.2105 | 0.2063 | 0.4482 | 0.056* | |
N2 | 0.15917 (10) | 0.1892 (6) | 0.4785 (3) | 0.0405 (9) | |
C1 | 0.1754 (2) | 0.3384 (13) | 0.9268 (9) | 0.110 | |
H1A | 0.1558 | 0.4215 | 0.9077 | 0.165* | |
H1B | 0.1869 | 0.3543 | 1.0149 | 0.165* | |
H1C | 0.1659 | 0.2211 | 0.9161 | 0.165* | |
C2 | 0.20340 (19) | 0.3672 (11) | 0.8349 (6) | 0.0778 (19) | |
H2A | 0.2102 | 0.4905 | 0.8340 | 0.093* | |
H2B | 0.2253 | 0.2990 | 0.8629 | 0.093* | |
C3 | 0.21109 (14) | 0.2866 (7) | 0.6248 (5) | 0.0476 (12) | |
C4 | 0.17159 (14) | 0.1219 (9) | 0.2542 (5) | 0.0546 (14) | |
H4A | 0.1804 | 0.2353 | 0.2321 | 0.082* | |
H4B | 0.1575 | 0.0706 | 0.1788 | 0.082* | |
H4C | 0.1921 | 0.0470 | 0.2838 | 0.082* | |
C5 | 0.14785 (12) | 0.1416 (6) | 0.3605 (4) | 0.0376 (10) | |
C6 | 0.10856 (12) | 0.1051 (6) | 0.3318 (4) | 0.0374 (10) | |
C7 | 0.08003 (13) | 0.1737 (7) | 0.3953 (4) | 0.0414 (10) | |
H7 | 0.0831 | 0.2526 | 0.4645 | 0.050* | |
C8 | 0.04652 (15) | 0.1046 (7) | 0.3379 (5) | 0.0494 (12) | |
H8 | 0.0236 | 0.1300 | 0.3616 | 0.059* | |
C9 | 0.05362 (15) | −0.0114 (7) | 0.2368 (5) | 0.0500 (12) | |
H9 | 0.0361 | −0.0758 | 0.1831 | 0.060* | |
C10 | 0.09188 (14) | −0.0121 (6) | 0.2319 (4) | 0.0438 (11) | |
H10 | 0.1040 | −0.0766 | 0.1746 | 0.053* | |
C11 | 0.06881 (18) | 0.5011 (8) | 0.1821 (5) | 0.0608 (15) | |
H11 | 0.0709 | 0.5818 | 0.2501 | 0.073* | |
C12 | 0.03581 (18) | 0.4243 (8) | 0.1213 (5) | 0.0619 (16) | |
H12 | 0.0124 | 0.4452 | 0.1419 | 0.074* | |
C13 | 0.04501 (18) | 0.3111 (8) | 0.0245 (5) | 0.0601 (15) | |
H13 | 0.0286 | 0.2434 | −0.0308 | 0.072* | |
C14 | 0.08348 (18) | 0.3164 (8) | 0.0246 (5) | 0.0588 (14) | |
H14 | 0.0967 | 0.2531 | −0.0302 | 0.071* | |
C15 | 0.09806 (17) | 0.4338 (8) | 0.1217 (6) | 0.0608 (15) | |
H15 | 0.1227 | 0.4626 | 0.1429 | 0.073* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Fe | 0.0478 (4) | 0.0327 (4) | 0.0242 (4) | 0.0027 (3) | −0.0050 (3) | 0.0026 (2) |
O1 | 0.059 (2) | 0.075 (3) | 0.0299 (16) | −0.0061 (19) | 0.0060 (15) | −0.0094 (17) |
O2 | 0.050 (2) | 0.126 (4) | 0.040 (2) | −0.013 (2) | −0.0021 (17) | −0.021 (2) |
N1 | 0.042 (2) | 0.070 (3) | 0.0276 (19) | 0.001 (2) | 0.0020 (16) | −0.0054 (18) |
N2 | 0.042 (2) | 0.052 (2) | 0.0255 (18) | 0.0018 (18) | −0.0045 (15) | −0.0002 (17) |
C1 | 0.110 | 0.110 | 0.110 | 0.000 | 0.015 | 0.000 |
C2 | 0.086 (4) | 0.103 (4) | 0.044 (3) | −0.023 (3) | 0.009 (3) | −0.020 (3) |
C3 | 0.046 (3) | 0.059 (3) | 0.035 (2) | 0.001 (2) | −0.004 (2) | 0.001 (2) |
C4 | 0.053 (3) | 0.077 (4) | 0.032 (2) | 0.003 (3) | 0.001 (2) | −0.008 (3) |
C5 | 0.046 (2) | 0.038 (2) | 0.026 (2) | 0.005 (2) | −0.0030 (18) | 0.0010 (18) |
C6 | 0.046 (2) | 0.036 (2) | 0.028 (2) | 0.0014 (19) | −0.0042 (18) | 0.0034 (17) |
C7 | 0.053 (3) | 0.043 (3) | 0.025 (2) | 0.000 (2) | −0.0025 (19) | 0.0043 (19) |
C8 | 0.050 (3) | 0.056 (3) | 0.042 (3) | 0.000 (2) | 0.004 (2) | 0.011 (2) |
C9 | 0.058 (3) | 0.041 (3) | 0.046 (3) | −0.012 (2) | −0.010 (2) | 0.004 (2) |
C10 | 0.061 (3) | 0.032 (2) | 0.035 (2) | 0.001 (2) | −0.006 (2) | −0.0015 (18) |
C11 | 0.095 (4) | 0.041 (2) | 0.043 (2) | 0.005 (3) | −0.003 (3) | 0.006 (2) |
C12 | 0.074 (4) | 0.059 (3) | 0.051 (3) | 0.029 (3) | 0.004 (3) | 0.022 (3) |
C13 | 0.076 (4) | 0.061 (3) | 0.037 (3) | 0.010 (3) | −0.015 (3) | 0.011 (2) |
C14 | 0.083 (4) | 0.059 (3) | 0.036 (3) | 0.005 (3) | 0.011 (3) | 0.012 (2) |
C15 | 0.067 (3) | 0.054 (3) | 0.056 (3) | −0.014 (3) | −0.011 (3) | 0.026 (3) |
Fe—C11 | 2.032 (6) | C4—H4A | 0.9600 |
Fe—C9 | 2.036 (5) | C4—H4B | 0.9600 |
Fe—C10 | 2.036 (5) | C4—H4C | 0.9600 |
Fe—C15 | 2.037 (5) | C5—C6 | 1.461 (6) |
Fe—C13 | 2.039 (5) | C6—C7 | 1.412 (7) |
Fe—C12 | 2.042 (5) | C6—C10 | 1.438 (6) |
Fe—C6 | 2.042 (4) | C7—C8 | 1.396 (7) |
Fe—C8 | 2.042 (5) | C7—H7 | 0.9300 |
Fe—C14 | 2.042 (5) | C8—C9 | 1.421 (8) |
Fe—C7 | 2.044 (4) | C8—H8 | 0.9300 |
O1—C2 | 1.453 (6) | C9—C10 | 1.415 (7) |
O1—C3 | 1.313 (6) | C9—H9 | 0.9300 |
O2—C3 | 1.216 (6) | C10—H10 | 0.9300 |
N1—N2 | 1.388 (5) | C11—C15 | 1.412 (9) |
N1—C3 | 1.353 (6) | C11—C12 | 1.415 (9) |
N1—H1N | 0.8600 | C11—H11 | 0.9300 |
N2—C5 | 1.290 (6) | C12—C13 | 1.398 (9) |
C1—C2 | 1.509 (8) | C12—H12 | 0.9300 |
C1—H1A | 0.9600 | C13—C14 | 1.415 (8) |
C1—H1B | 0.9600 | C13—H13 | 0.9300 |
C1—H1C | 0.9600 | C14—C15 | 1.397 (9) |
C2—H2A | 0.9700 | C14—H14 | 0.9300 |
C2—H2B | 0.9700 | C15—H15 | 0.9300 |
C4—C5 | 1.503 (7) | ||
C11—Fe—C9 | 157.4 (2) | H4A—C4—H4B | 109.5 |
C11—Fe—C10 | 161.0 (2) | C5—C4—H4C | 109.5 |
C9—Fe—C10 | 40.7 (2) | H4A—C4—H4C | 109.5 |
C11—Fe—C15 | 40.6 (2) | H4B—C4—H4C | 109.5 |
C9—Fe—C15 | 160.0 (3) | N2—C5—C4 | 125.4 (4) |
C10—Fe—C15 | 123.9 (2) | N2—C5—C6 | 115.4 (4) |
C11—Fe—C13 | 67.6 (2) | C4—C5—C6 | 119.2 (4) |
C9—Fe—C13 | 107.3 (2) | C7—C6—C10 | 107.1 (4) |
C10—Fe—C13 | 121.4 (2) | C7—C6—C5 | 127.7 (4) |
C15—Fe—C13 | 67.7 (2) | C10—C6—C5 | 125.3 (4) |
C11—Fe—C12 | 40.7 (2) | C7—C6—Fe | 69.8 (2) |
C9—Fe—C12 | 121.2 (2) | C10—C6—Fe | 69.1 (3) |
C10—Fe—C12 | 156.4 (2) | C5—C6—Fe | 126.7 (3) |
C15—Fe—C12 | 68.3 (3) | C8—C7—C6 | 109.3 (4) |
C13—Fe—C12 | 40.1 (2) | C8—C7—Fe | 69.9 (3) |
C11—Fe—C6 | 124.4 (2) | C6—C7—Fe | 69.7 (2) |
C9—Fe—C6 | 68.71 (19) | C8—C7—H7 | 125.3 |
C10—Fe—C6 | 41.31 (18) | C6—C7—H7 | 125.3 |
C15—Fe—C6 | 108.1 (2) | Fe—C7—H7 | 126.6 |
C13—Fe—C6 | 157.7 (2) | C7—C8—C9 | 107.9 (5) |
C12—Fe—C6 | 160.9 (2) | C7—C8—Fe | 70.1 (3) |
C11—Fe—C8 | 122.3 (2) | C9—C8—Fe | 69.4 (3) |
C9—Fe—C8 | 40.8 (2) | C7—C8—H8 | 126.0 |
C10—Fe—C8 | 68.6 (2) | C9—C8—H8 | 126.0 |
C15—Fe—C8 | 158.1 (2) | Fe—C8—H8 | 126.1 |
C13—Fe—C8 | 123.9 (2) | C10—C9—C8 | 108.2 (4) |
C12—Fe—C8 | 107.6 (2) | C10—C9—Fe | 69.7 (3) |
C6—Fe—C8 | 68.2 (2) | C8—C9—Fe | 69.8 (3) |
C11—Fe—C14 | 67.9 (2) | C10—C9—H9 | 125.9 |
C9—Fe—C14 | 123.6 (2) | C8—C9—H9 | 125.9 |
C10—Fe—C14 | 107.2 (2) | Fe—C9—H9 | 126.2 |
C15—Fe—C14 | 40.1 (2) | C9—C10—C6 | 107.5 (4) |
C13—Fe—C14 | 40.6 (2) | C9—C10—Fe | 69.7 (3) |
C12—Fe—C14 | 68.1 (2) | C6—C10—Fe | 69.6 (3) |
C6—Fe—C14 | 122.1 (2) | C9—C10—H10 | 126.2 |
C8—Fe—C14 | 160.3 (2) | C6—C10—H10 | 126.2 |
C11—Fe—C7 | 108.9 (2) | Fe—C10—H10 | 126.1 |
C9—Fe—C7 | 67.9 (2) | C15—C11—C12 | 108.1 (5) |
C10—Fe—C7 | 68.38 (19) | C15—C11—Fe | 69.9 (3) |
C15—Fe—C7 | 123.3 (2) | C12—C11—Fe | 70.1 (3) |
C13—Fe—C7 | 160.2 (2) | C15—C11—H11 | 125.9 |
C12—Fe—C7 | 124.6 (2) | C12—C11—H11 | 125.9 |
C6—Fe—C7 | 40.44 (19) | Fe—C11—H11 | 125.7 |
C8—Fe—C7 | 40.0 (2) | C13—C12—C11 | 107.3 (6) |
C14—Fe—C7 | 158.1 (2) | C13—C12—Fe | 69.8 (3) |
C2—O1—C3 | 113.7 (4) | C11—C12—Fe | 69.3 (3) |
C3—N1—N2 | 121.1 (4) | C13—C12—H12 | 126.3 |
C3—N1—H1N | 119.4 | C11—C12—H12 | 126.3 |
N2—N1—H1N | 119.4 | Fe—C12—H12 | 126.1 |
C5—N2—N1 | 115.8 (4) | C12—C13—C14 | 108.8 (6) |
C2—C1—H1A | 109.5 | C12—C13—Fe | 70.1 (3) |
C2—C1—H1B | 109.5 | C14—C13—Fe | 69.8 (3) |
H1A—C1—H1B | 109.5 | C12—C13—H13 | 125.6 |
C2—C1—H1C | 109.5 | C14—C13—H13 | 125.6 |
H1A—C1—H1C | 109.5 | Fe—C13—H13 | 126.0 |
H1B—C1—H1C | 109.5 | C15—C14—C13 | 107.7 (6) |
O1—C2—C1 | 107.9 (6) | C15—C14—Fe | 69.8 (3) |
O1—C2—H2A | 110.1 | C13—C14—Fe | 69.6 (3) |
C1—C2—H2A | 110.1 | C15—C14—H14 | 126.2 |
O1—C2—H2B | 110.1 | C13—C14—H14 | 126.2 |
C1—C2—H2B | 110.1 | Fe—C14—H14 | 126.1 |
H2A—C2—H2B | 108.4 | C14—C15—C11 | 108.1 (5) |
O1—C3—O2 | 124.2 (5) | C14—C15—Fe | 70.2 (3) |
O1—C3—N1 | 114.3 (4) | C11—C15—Fe | 69.5 (3) |
O2—C3—N1 | 121.6 (5) | C14—C15—H15 | 126.0 |
C5—C4—H4A | 109.5 | C11—C15—H15 | 126.0 |
C5—C4—H4B | 109.5 | Fe—C15—H15 | 126.0 |
C3—N1—N2—C5 | 175.5 (5) | C12—Fe—C10—C9 | −47.4 (7) |
C3—O1—C2—C1 | −163.0 (6) | C6—Fe—C10—C9 | 118.7 (4) |
C2—O1—C3—O2 | −4.1 (9) | C8—Fe—C10—C9 | 37.7 (3) |
C2—O1—C3—N1 | 176.0 (5) | C14—Fe—C10—C9 | −121.9 (3) |
N2—N1—C3—O2 | 179.0 (5) | C7—Fe—C10—C9 | 80.8 (3) |
N2—N1—C3—O1 | −1.1 (7) | C11—Fe—C10—C6 | 47.6 (7) |
N1—N2—C5—C6 | −180.0 (4) | C9—Fe—C10—C6 | −118.7 (4) |
N1—N2—C5—C4 | 0.1 (7) | C15—Fe—C10—C6 | 78.6 (3) |
N2—C5—C6—C7 | 25.7 (7) | C13—Fe—C10—C6 | 161.4 (3) |
C4—C5—C6—C7 | −154.3 (5) | C12—Fe—C10—C6 | −166.1 (5) |
N2—C5—C6—C10 | −153.5 (5) | C8—Fe—C10—C6 | −81.0 (3) |
C4—C5—C6—C10 | 26.5 (7) | C14—Fe—C10—C6 | 119.4 (3) |
N2—C5—C6—Fe | 117.6 (4) | C7—Fe—C10—C6 | −37.9 (3) |
C4—C5—C6—Fe | −62.5 (6) | C9—Fe—C11—C15 | −162.6 (5) |
C11—Fe—C6—C7 | 78.6 (4) | C10—Fe—C11—C15 | 41.1 (8) |
C9—Fe—C6—C7 | −80.5 (3) | C13—Fe—C11—C15 | −81.4 (4) |
C10—Fe—C6—C7 | −118.3 (4) | C12—Fe—C11—C15 | −119.1 (5) |
C15—Fe—C6—C7 | 120.5 (3) | C6—Fe—C11—C15 | 77.3 (4) |
C13—Fe—C6—C7 | −164.2 (6) | C8—Fe—C11—C15 | 161.6 (3) |
C12—Fe—C6—C7 | 44.6 (8) | C14—Fe—C11—C15 | −37.4 (3) |
C8—Fe—C6—C7 | −36.5 (3) | C7—Fe—C11—C15 | 119.5 (3) |
C14—Fe—C6—C7 | 162.3 (3) | C9—Fe—C11—C12 | −43.6 (7) |
C11—Fe—C6—C10 | −163.1 (3) | C10—Fe—C11—C12 | 160.1 (6) |
C9—Fe—C6—C10 | 37.8 (3) | C15—Fe—C11—C12 | 119.1 (5) |
C15—Fe—C6—C10 | −121.2 (3) | C13—Fe—C11—C12 | 37.7 (4) |
C13—Fe—C6—C10 | −45.8 (7) | C6—Fe—C11—C12 | −163.7 (3) |
C12—Fe—C6—C10 | 162.9 (7) | C8—Fe—C11—C12 | −79.3 (4) |
C8—Fe—C6—C10 | 81.8 (3) | C14—Fe—C11—C12 | 81.7 (4) |
C14—Fe—C6—C10 | −79.3 (4) | C7—Fe—C11—C12 | −121.4 (3) |
C7—Fe—C6—C10 | 118.3 (4) | C15—C11—C12—C13 | 0.0 (6) |
C11—Fe—C6—C5 | −44.0 (5) | Fe—C11—C12—C13 | −59.8 (4) |
C9—Fe—C6—C5 | 156.9 (5) | C15—C11—C12—Fe | 59.7 (4) |
C10—Fe—C6—C5 | 119.1 (5) | C11—Fe—C12—C13 | 118.5 (5) |
C15—Fe—C6—C5 | −2.1 (5) | C9—Fe—C12—C13 | −79.5 (4) |
C13—Fe—C6—C5 | 73.3 (8) | C10—Fe—C12—C13 | −45.4 (8) |
C12—Fe—C6—C5 | −78.0 (8) | C15—Fe—C12—C13 | 80.7 (4) |
C8—Fe—C6—C5 | −159.1 (5) | C6—Fe—C12—C13 | 163.5 (6) |
C14—Fe—C6—C5 | 39.7 (5) | C8—Fe—C12—C13 | −122.1 (4) |
C7—Fe—C6—C5 | −122.6 (5) | C14—Fe—C12—C13 | 37.5 (4) |
C10—C6—C7—C8 | −0.5 (5) | C7—Fe—C12—C13 | −162.9 (4) |
C5—C6—C7—C8 | −179.8 (4) | C9—Fe—C12—C11 | 161.9 (3) |
Fe—C6—C7—C8 | 58.9 (3) | C10—Fe—C12—C11 | −164.0 (5) |
C10—C6—C7—Fe | −59.3 (3) | C15—Fe—C12—C11 | −37.8 (3) |
C5—C6—C7—Fe | 121.3 (5) | C13—Fe—C12—C11 | −118.5 (5) |
C11—Fe—C7—C8 | 118.0 (4) | C6—Fe—C12—C11 | 45.0 (8) |
C9—Fe—C7—C8 | −38.0 (3) | C8—Fe—C12—C11 | 119.4 (4) |
C10—Fe—C7—C8 | −82.0 (3) | C14—Fe—C12—C11 | −81.1 (4) |
C15—Fe—C7—C8 | 160.7 (3) | C7—Fe—C12—C11 | 78.6 (4) |
C13—Fe—C7—C8 | 41.6 (8) | C11—C12—C13—C14 | 0.1 (6) |
C12—Fe—C7—C8 | 75.6 (4) | Fe—C12—C13—C14 | −59.3 (4) |
C6—Fe—C7—C8 | −120.7 (4) | C11—C12—C13—Fe | 59.4 (4) |
C14—Fe—C7—C8 | −164.4 (6) | C11—Fe—C13—C12 | −38.2 (4) |
C11—Fe—C7—C6 | −121.3 (3) | C9—Fe—C13—C12 | 118.3 (4) |
C9—Fe—C7—C6 | 82.7 (3) | C10—Fe—C13—C12 | 160.5 (4) |
C10—Fe—C7—C6 | 38.7 (3) | C15—Fe—C13—C12 | −82.3 (4) |
C15—Fe—C7—C6 | −78.6 (4) | C6—Fe—C13—C12 | −165.8 (5) |
C13—Fe—C7—C6 | 162.2 (6) | C8—Fe—C13—C12 | 76.6 (5) |
C12—Fe—C7—C6 | −163.8 (3) | C14—Fe—C13—C12 | −119.8 (6) |
C8—Fe—C7—C6 | 120.7 (4) | C7—Fe—C13—C12 | 45.7 (9) |
C14—Fe—C7—C6 | −43.7 (7) | C11—Fe—C13—C14 | 81.6 (4) |
C6—C7—C8—C9 | 0.5 (6) | C9—Fe—C13—C14 | −121.9 (4) |
Fe—C7—C8—C9 | 59.3 (3) | C10—Fe—C13—C14 | −79.7 (4) |
C6—C7—C8—Fe | −58.7 (3) | C15—Fe—C13—C14 | 37.5 (4) |
C11—Fe—C8—C7 | −81.0 (4) | C12—Fe—C13—C14 | 119.8 (6) |
C9—Fe—C8—C7 | 119.1 (4) | C6—Fe—C13—C14 | −46.0 (8) |
C10—Fe—C8—C7 | 81.5 (3) | C8—Fe—C13—C14 | −163.6 (4) |
C15—Fe—C8—C7 | −47.7 (7) | C7—Fe—C13—C14 | 165.5 (6) |
C13—Fe—C8—C7 | −164.3 (3) | C12—C13—C14—C15 | −0.1 (6) |
C12—Fe—C8—C7 | −123.2 (3) | Fe—C13—C14—C15 | −59.6 (4) |
C6—Fe—C8—C7 | 36.9 (3) | C12—C13—C14—Fe | 59.5 (4) |
C14—Fe—C8—C7 | 162.6 (6) | C11—Fe—C14—C15 | 37.9 (4) |
C11—Fe—C8—C9 | 159.9 (3) | C9—Fe—C14—C15 | −164.3 (4) |
C10—Fe—C8—C9 | −37.6 (3) | C10—Fe—C14—C15 | −122.7 (4) |
C15—Fe—C8—C9 | −166.8 (5) | C13—Fe—C14—C15 | 118.9 (5) |
C13—Fe—C8—C9 | 76.6 (4) | C12—Fe—C14—C15 | 81.9 (4) |
C12—Fe—C8—C9 | 117.7 (3) | C6—Fe—C14—C15 | −79.9 (4) |
C6—Fe—C8—C9 | −82.2 (3) | C8—Fe—C14—C15 | 163.0 (6) |
C14—Fe—C8—C9 | 43.5 (8) | C7—Fe—C14—C15 | −48.0 (8) |
C7—Fe—C8—C9 | −119.1 (4) | C11—Fe—C14—C13 | −81.0 (4) |
C7—C8—C9—C10 | −0.4 (6) | C9—Fe—C14—C13 | 76.8 (4) |
Fe—C8—C9—C10 | 59.3 (3) | C10—Fe—C14—C13 | 118.5 (4) |
C7—C8—C9—Fe | −59.7 (3) | C15—Fe—C14—C13 | −118.9 (5) |
C11—Fe—C9—C10 | −168.4 (5) | C12—Fe—C14—C13 | −37.0 (4) |
C15—Fe—C9—C10 | 46.2 (7) | C6—Fe—C14—C13 | 161.2 (3) |
C13—Fe—C9—C10 | 118.4 (3) | C8—Fe—C14—C13 | 44.1 (9) |
C12—Fe—C9—C10 | 159.9 (3) | C7—Fe—C14—C13 | −166.8 (5) |
C6—Fe—C9—C10 | −38.4 (3) | C13—C14—C15—C11 | 0.1 (6) |
C8—Fe—C9—C10 | −119.4 (4) | Fe—C14—C15—C11 | −59.4 (4) |
C14—Fe—C9—C10 | 76.8 (4) | C13—C14—C15—Fe | 59.5 (4) |
C7—Fe—C9—C10 | −82.1 (3) | C12—C11—C15—C14 | −0.1 (6) |
C11—Fe—C9—C8 | −49.1 (7) | Fe—C11—C15—C14 | 59.8 (4) |
C10—Fe—C9—C8 | 119.4 (4) | C12—C11—C15—Fe | −59.8 (4) |
C15—Fe—C9—C8 | 165.5 (6) | C11—Fe—C15—C14 | −119.2 (5) |
C13—Fe—C9—C8 | −122.3 (3) | C9—Fe—C15—C14 | 41.2 (8) |
C12—Fe—C9—C8 | −80.8 (4) | C10—Fe—C15—C14 | 75.7 (4) |
C6—Fe—C9—C8 | 80.9 (3) | C13—Fe—C15—C14 | −38.0 (4) |
C14—Fe—C9—C8 | −163.8 (3) | C12—Fe—C15—C14 | −81.4 (4) |
C7—Fe—C9—C8 | 37.3 (3) | C6—Fe—C15—C14 | 118.7 (4) |
C8—C9—C10—C6 | 0.1 (5) | C8—Fe—C15—C14 | −164.7 (5) |
Fe—C9—C10—C6 | 59.5 (3) | C7—Fe—C15—C14 | 160.7 (3) |
C8—C9—C10—Fe | −59.4 (3) | C9—Fe—C15—C11 | 160.4 (6) |
C7—C6—C10—C9 | 0.2 (5) | C10—Fe—C15—C11 | −165.1 (3) |
C5—C6—C10—C9 | 179.6 (4) | C13—Fe—C15—C11 | 81.2 (4) |
Fe—C6—C10—C9 | −59.6 (3) | C12—Fe—C15—C11 | 37.8 (3) |
C7—C6—C10—Fe | 59.8 (3) | C6—Fe—C15—C11 | −122.2 (3) |
C5—C6—C10—Fe | −120.9 (4) | C8—Fe—C15—C11 | −45.5 (7) |
C11—Fe—C10—C9 | 166.3 (6) | C14—Fe—C15—C11 | 119.2 (5) |
C15—Fe—C10—C9 | −162.7 (3) | C7—Fe—C15—C11 | −80.2 (4) |
C13—Fe—C10—C9 | −79.9 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O2i | 0.86 | 2.09 | 2.927 (6) | 164 |
C4—H4C···O2i | 0.96 | 2.58 | 3.170 (7) | 119 |
Symmetry code: (i) −x+1/2, −y+1/2, −z+1. |
Experimental details
Crystal data | |
Chemical formula | [Fe(C5H5)(C10H13N2O2] |
Mr | 314.16 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 295 |
a, b, c (Å) | 36.770 (7), 7.6040 (15), 10.366 (2) |
β (°) | 97.82 (3) |
V (Å3) | 2871.4 (10) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 1.05 |
Crystal size (mm) | 0.40 × 0.20 × 0.20 |
Data collection | |
Diffractometer | Enraf–Nonius CAD4 diffractometer |
Absorption correction | Empirical (using intensity measurements) via ψ scan (North et al., 1968) |
Tmin, Tmax | 0.747, 0.803 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 2848, 2804, 2178 |
Rint | 0.039 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.060, 0.184, 1.07 |
No. of reflections | 2804 |
No. of parameters | 177 |
No. of restraints | 13 |
H-atom treatment | H-atom parameters constrained |
w = 1/[σ2(Fo2) + (0.098P)2 + 11.3526P] where P = (Fo2 + 2Fc2)/3 | |
Δρmax, Δρmin (e Å−3) | 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.
O1—C2 | 1.453 (6) | N2—C5 | 1.290 (6) |
O1—C3 | 1.313 (6) | C1—C2 | 1.509 (8) |
O2—C3 | 1.216 (6) | C4—C5 | 1.503 (7) |
N1—C3 | 1.353 (6) | C5—C6 | 1.461 (6) |
O1—C2—C1 | 107.9 (6) | N2—C5—C4 | 125.4 (4) |
O1—C3—O2 | 124.2 (5) | N2—C5—C6 | 115.4 (4) |
O1—C3—N1 | 114.3 (4) | C4—C5—C6 | 119.2 (4) |
O2—C3—N1 | 121.6 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O2i | 0.86 | 2.09 | 2.927 (6) | 164 |
Symmetry code: (i) −x+1/2, −y+1/2, −z+1. |
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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 C═O, while the ethyl group adopts a cis geometry. The ferrocenyl and ethyl groups are cis to each other across the N1—N2 and C═O bonds. Moreover, both cyclopentadienyl rings in the ferrocenyl group are in the eclipsed conformation. The bond lengths and angles of the C═N—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 C═N—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···O═C hydrogen bonds lead to the formation of centrosymmetric R22(8) dimers (Bernstein et al., 1995; Table 2; Fig. 2).