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The title compound, [Fe(C5H5)(C8H7O)], is produced by the reaction of ferrocene with 1,1,3,3-tetra­methoxy­propane. It crystallizes in the noncentrosymmetric space group P212121. The α,β-unsaturated aldehyde moiety adopts an s-trans configuration. The crystal structure is stabilized by inter­molecular C—H...O interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804019129/br6159sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804019129/br6159Isup2.hkl
Contains datablock I

CCDC reference: 251585

Key indicators

  • Single-crystal X-ray study
  • T = 183 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.017
  • wR factor = 0.051
  • Data-to-parameter ratio = 10.5

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............ 23.29 Deg.
Author Response: Unfortunately, it is not possible to solve the problem regarding the resolution of the dataset. The analysis has been undertaken some time ago with a version of DENZO that was not able to measure at higher angles. So although the data were only recorded up to 23.26 degrees in theta, more than 90 percent of the measured reflections have I > 2 sigma, which leads to a satisfactory data parameter ratio. I would be very pleased if it was possible to accept the structure for publication in Acta Cryst. E despite the fact, that the resolution formally does not reach the standards of the journal.
PLAT035_ALERT_1_A No _chemical_absolute_configuration info given .          ?
Author Response: Although the compound crysallizes in a chiral space group, the compound itself is achiral. So no absolute configuration of the molecule can be determined.
PLAT726_ALERT_1_A H...A   Calc     2.69237, Rep     2.54500 Dev...       0.15 Ang.
              H2   -O1      1.555   4.475
PLAT726_ALERT_1_A H...A   Calc     2.45532, Rep     2.30800 Dev...       0.15 Ang.
              H8   -O1      1.555   4.475
PLAT726_ALERT_1_A H...A   Calc     2.50856, Rep     2.39500 Dev...       0.11 Ang.
              H5   -O1      1.555   2.675
PLAT726_ALERT_1_A H...A   Calc     2.64248, Rep     2.49600 Dev...       0.15 Ang.
              H6   -O1      1.555   3.645
PLAT728_ALERT_1_A D-H..A  Calc      140.88, Rep      137.00 Dev...       3.88 Deg.
              C5   -H5   -O1      1.555   1.555   2.675

Alert level B THETM01_ALERT_3_B The value of sine(theta_max)/wavelength is less than 0.575 Calculated sin(theta_max)/wavelength = 0.5563 PLAT023_ALERT_3_B Resolution (too) Low [sin(th)/Lambda < 0.6]..... 23.29 Deg.
Alert level C STRVA01_ALERT_4_C Flack test results are ambiguous. From the CIF: _refine_ls_abs_structure_Flack 0.444 From the CIF: _refine_ls_abs_structure_Flack_su 0.019 PLAT033_ALERT_2_C Flack Parameter Value Deviates from Zero ....... 0.44 PLAT711_ALERT_1_C BOND Unknown or Inconsistent Label .......... C~CP~ FE1 C~CP~ PLAT728_ALERT_1_C D-H..A Calc 169.10, Rep 168.00 Dev... 1.10 Deg. C6 -H6 -O1 1.555 1.555 3.645 PLAT747_ALERT_1_C D...A Calc 3.609(2), Rep 3.60900 ...... Missing su C2 -O1 1.555 4.475 PLAT747_ALERT_1_C D...A Calc 3.369(2), Rep 3.36900 ...... Missing su C8 -O1 1.555 4.475 PLAT747_ALERT_1_C D...A Calc 3.283(2), Rep 3.28300 ...... Missing su C5 -O1 1.555 2.675 PLAT747_ALERT_1_C D...A Calc 3.560(2), Rep 3.56000 ...... Missing su C6 -O1 1.555 3.645
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 23.29 From the CIF: _reflns_number_total 1570 Count of symmetry unique reflns 946 Completeness (_total/calc) 165.96% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 624 Fraction of Friedel pairs measured 0.660 Are heavy atom types Z>Si present yes
7 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 12 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 3 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1990); software used to prepare material for publication: XP.

3-ferrocenylprop-2-enal top
Crystal data top
[Fe(C5H5)(C8H7O)]F(000) = 496
Mr = 240.08Dx = 1.452 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 1570 reflections
a = 7.9192 (2) Åθ = 3.8–23.3°
b = 11.1648 (3) ŵ = 1.34 mm1
c = 12.4204 (4) ÅT = 183 K
V = 1098.17 (5) Å3Cuboid, red
Z = 40.5 × 0.2 × 0.2 mm
Data collection top
Nonius KappaCCD
diffractometer
1541 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.016
Graphite monochromatorθmax = 23.3°, θmin = 3.8°
ω scanh = 08
2961 measured reflectionsk = 1212
1570 independent reflectionsl = 1313
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.017Only H-atom displacement parameters refined
wR(F2) = 0.051 w = 1/[σ2(Fo2) + (0.0319P)2 + 0.0364P]
where P = (Fo2 + 2Fc2)/3
S = 1.11(Δ/σ)max = 0.001
1570 reflectionsΔρmax = 0.13 e Å3
149 parametersΔρmin = 0.17 e Å3
0 restraintsAbsolute structure: Flack (1983), 624 Friedel pairs?
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.444 (19)
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
Fe10.24505 (3)0.873351 (18)0.213074 (15)0.02765 (12)
O10.69426 (16)1.20463 (11)0.08622 (9)0.0411 (3)
C10.6811 (2)1.11649 (16)0.02879 (14)0.0336 (4)
H10.75601.05360.04030.036 (5)*
C20.5572 (2)1.10281 (15)0.05585 (12)0.0295 (4)
H20.47501.16140.06510.031 (4)*
C30.5583 (2)1.00710 (14)0.12144 (13)0.0311 (4)
H30.63780.94780.10750.037 (5)*
C40.4459 (2)0.98857 (15)0.21226 (13)0.0305 (4)
C50.4659 (2)0.89883 (16)0.29428 (13)0.0345 (4)
H50.55390.84390.29930.029 (4)*
C60.3268 (2)0.90902 (15)0.36661 (14)0.0380 (4)
H60.30860.86210.42740.045 (5)*
C70.2209 (3)1.00325 (15)0.32982 (14)0.0386 (4)
H70.12131.02840.36250.055 (6)*
C80.2926 (2)1.05274 (15)0.23482 (14)0.0331 (4)
H80.24821.11540.19450.037 (5)*
C90.0850 (3)0.8540 (2)0.08396 (15)0.0484 (5)
H90.04420.91520.04030.074 (8)*
C100.0078 (3)0.8105 (2)0.18015 (16)0.0520 (6)
H100.09220.83840.21040.070 (8)*
C110.1104 (3)0.71711 (19)0.22152 (17)0.0534 (6)
H110.08980.67330.28380.075 (8)*
C120.2490 (3)0.70237 (17)0.15176 (15)0.0525 (5)
H120.33540.64670.15970.078 (8)*
C130.2339 (3)0.78766 (17)0.06696 (14)0.0461 (5)
H130.30920.79780.01030.045 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.02772 (17)0.02787 (18)0.02737 (17)0.00143 (12)0.00091 (10)0.00421 (8)
O10.0459 (8)0.0394 (7)0.0380 (7)0.0051 (6)0.0095 (5)0.0059 (6)
C10.0323 (9)0.0302 (9)0.0383 (9)0.0023 (8)0.0041 (7)0.0050 (9)
C20.0274 (8)0.0294 (8)0.0317 (8)0.0017 (7)0.0020 (6)0.0014 (7)
C30.0250 (9)0.0292 (9)0.0392 (9)0.0017 (7)0.0000 (7)0.0007 (8)
C40.0317 (9)0.0275 (9)0.0322 (9)0.0030 (7)0.0038 (7)0.0034 (7)
C50.0341 (10)0.0326 (9)0.0368 (10)0.0032 (8)0.0094 (7)0.0081 (7)
C60.0487 (11)0.0353 (10)0.0300 (9)0.0048 (8)0.0020 (8)0.0050 (8)
C70.0475 (11)0.0346 (9)0.0337 (9)0.0007 (9)0.0099 (9)0.0001 (7)
C80.0396 (11)0.0257 (8)0.0339 (9)0.0029 (7)0.0035 (8)0.0018 (7)
C90.0477 (12)0.0633 (13)0.0343 (10)0.0102 (11)0.0129 (9)0.0058 (10)
C100.0337 (11)0.0772 (15)0.0451 (11)0.0159 (11)0.0069 (10)0.0045 (11)
C110.0604 (15)0.0497 (13)0.0502 (12)0.0287 (11)0.0086 (10)0.0086 (10)
C120.0693 (15)0.0318 (9)0.0563 (12)0.0073 (11)0.0093 (13)0.0085 (8)
C130.0529 (13)0.0494 (11)0.0362 (10)0.0109 (11)0.0004 (10)0.0087 (8)
Geometric parameters (Å, º) top
Fe1—C52.0389 (18)C5—C61.426 (3)
Fe1—C42.0456 (17)C5—H50.9300
Fe1—C102.0469 (19)C6—C71.421 (3)
Fe1—C112.047 (2)C6—H60.9300
Fe1—C92.0556 (18)C7—C81.421 (3)
Fe1—C132.0534 (17)C7—H70.9300
Fe1—C82.0558 (17)C8—H80.9300
Fe1—C62.0528 (18)C9—C131.408 (3)
Fe1—C122.0555 (18)C9—C101.427 (3)
Fe1—C72.0597 (17)C9—H90.9300
O1—C11.220 (2)C10—C111.418 (3)
C1—C21.446 (2)C10—H100.9300
C1—H10.9300C11—C121.408 (3)
C2—C31.344 (2)C11—H110.9300
C2—H20.9300C12—C131.425 (3)
C3—C41.452 (2)C12—H120.9300
C3—H30.9300C13—H130.9300
C4—C81.437 (3)Fe1—Ccp2.051 (2)
C4—C51.438 (2)
C5—Fe1—C441.21 (6)C8—C4—Fe169.87 (10)
C5—Fe1—C10159.07 (7)C5—C4—Fe169.14 (10)
C4—Fe1—C10158.18 (8)C3—C4—Fe1124.77 (11)
C5—Fe1—C11122.71 (8)C6—C5—C4107.80 (16)
C4—Fe1—C11160.23 (9)C6—C5—Fe170.13 (11)
C10—Fe1—C1140.52 (10)C4—C5—Fe169.64 (10)
C5—Fe1—C9158.37 (8)C6—C5—H5126.1
C4—Fe1—C9122.80 (7)C4—C5—H5126.1
C10—Fe1—C940.72 (8)Fe1—C5—H5125.7
C11—Fe1—C968.23 (9)C5—C6—C7108.20 (16)
C5—Fe1—C13122.63 (8)C5—C6—Fe169.08 (10)
C4—Fe1—C13108.79 (7)C7—C6—Fe170.05 (10)
C10—Fe1—C1367.92 (9)C5—C6—H6125.9
C11—Fe1—C1368.03 (8)C7—C6—H6125.9
C9—Fe1—C1340.09 (8)Fe1—C6—H6126.5
C5—Fe1—C869.02 (7)C8—C7—C6108.61 (17)
C4—Fe1—C841.02 (7)C8—C7—Fe169.65 (10)
C10—Fe1—C8121.91 (9)C6—C7—Fe169.53 (10)
C11—Fe1—C8156.76 (9)C8—C7—H7125.7
C9—Fe1—C8108.53 (8)C6—C7—H7125.7
C13—Fe1—C8125.30 (7)Fe1—C7—H7126.7
C5—Fe1—C640.79 (7)C7—C8—C4107.78 (16)
C4—Fe1—C668.74 (7)C7—C8—Fe169.95 (10)
C10—Fe1—C6122.79 (8)C4—C8—Fe169.11 (9)
C11—Fe1—C6106.38 (8)C7—C8—H8126.1
C9—Fe1—C6159.98 (8)C4—C8—H8126.1
C13—Fe1—C6157.66 (8)Fe1—C8—H8126.4
C8—Fe1—C668.36 (7)C13—C9—C10107.75 (18)
C5—Fe1—C12107.44 (9)C13—C9—Fe169.87 (10)
C4—Fe1—C12124.77 (8)C10—C9—Fe169.32 (10)
C10—Fe1—C1267.76 (10)C13—C9—H9126.1
C11—Fe1—C1240.15 (9)C10—C9—H9126.1
C9—Fe1—C1267.84 (9)Fe1—C9—H9126.3
C13—Fe1—C1240.58 (8)C11—C10—C9107.96 (19)
C8—Fe1—C12161.93 (8)C11—C10—Fe169.75 (11)
C6—Fe1—C12121.30 (8)C9—C10—Fe169.97 (10)
C5—Fe1—C768.48 (8)C11—C10—H10126.0
C4—Fe1—C768.46 (7)C9—C10—H10126.0
C10—Fe1—C7107.28 (9)Fe1—C10—H10125.8
C11—Fe1—C7121.04 (8)C12—C11—C10108.04 (18)
C9—Fe1—C7124.47 (8)C12—C11—Fe170.25 (11)
C13—Fe1—C7161.13 (8)C10—C11—Fe169.73 (12)
C8—Fe1—C740.40 (7)C12—C11—H11126.0
C6—Fe1—C740.43 (7)C10—C11—H11126.0
C12—Fe1—C7156.37 (7)Fe1—C11—H11125.6
O1—C1—C2124.63 (17)C11—C12—C13108.12 (19)
O1—C1—H1117.7C11—C12—Fe169.61 (11)
C2—C1—H1117.7C13—C12—Fe169.63 (10)
C3—C2—C1121.34 (16)C11—C12—H12125.9
C3—C2—H2119.3C13—C12—H12125.9
C1—C2—H2119.3Fe1—C12—H12126.4
C2—C3—C4125.46 (16)C9—C13—C12108.12 (18)
C2—C3—H3117.3C9—C13—Fe170.04 (11)
C4—C3—H3117.3C12—C13—Fe169.79 (10)
C8—C4—C5107.60 (15)C9—C13—H13125.9
C8—C4—C3126.76 (14)C12—C13—H13125.9
C5—C4—C3125.61 (16)Fe1—C13—H13125.8
Hydrogen-bond geometry (Å, º) top
D—H···AH···AD···AD—H···A
C2—H2···O1i2.553.609168
C8—H8···O1i2.313.369167
C5—H5···O1ii2.403.283137
C6—H6···O1iii2.503.560168
Symmetry codes: (i) x1/2, y+5/2, z; (ii) x+3/2, y+2, z+1/2; (iii) x+1, y1/2, z+1/2.
 

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