The title compound, [Fe(C
5H
5)(C
8H
7O)], is produced by the reaction of ferrocene with 1,1,3,3-tetramethoxypropane. It crystallizes in the noncentrosymmetric space group
P2
12
12
1. The α,β-unsaturated aldehyde moiety adopts an
s-trans configuration. The crystal structure is stabilized by intermolecular C—H
O interactions.
Supporting information
CCDC reference: 251585
Key indicators
- Single-crystal X-ray study
- T = 183 K
- Mean (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
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 = 240.08 | Dx = 1.452 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 1570 reflections |
a = 7.9192 (2) Å | θ = 3.8–23.3° |
b = 11.1648 (3) Å | µ = 1.34 mm−1 |
c = 12.4204 (4) Å | T = 183 K |
V = 1098.17 (5) Å3 | Cuboid, red |
Z = 4 | 0.5 × 0.2 × 0.2 mm |
Data collection top
Nonius KappaCCD diffractometer | 1541 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.016 |
Graphite monochromator | θmax = 23.3°, θmin = 3.8° |
ω scan | h = 0→8 |
2961 measured reflections | k = −12→12 |
1570 independent reflections | l = −13→13 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.017 | Only 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 reflections | Δρmax = 0.13 e Å−3 |
149 parameters | Δρmin = −0.17 e Å−3 |
0 restraints | Absolute structure: Flack (1983), 624 Friedel pairs? |
Primary atom site location: structure-invariant direct methods | Absolute 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 | x | y | z | Uiso*/Ueq | |
Fe1 | 0.24505 (3) | 0.873351 (18) | 0.213074 (15) | 0.02765 (12) | |
O1 | 0.69426 (16) | 1.20463 (11) | −0.08622 (9) | 0.0411 (3) | |
C1 | 0.6811 (2) | 1.11649 (16) | −0.02879 (14) | 0.0336 (4) | |
H1 | 0.7560 | 1.0536 | −0.0403 | 0.036 (5)* | |
C2 | 0.5572 (2) | 1.10281 (15) | 0.05585 (12) | 0.0295 (4) | |
H2 | 0.4750 | 1.1614 | 0.0651 | 0.031 (4)* | |
C3 | 0.5583 (2) | 1.00710 (14) | 0.12144 (13) | 0.0311 (4) | |
H3 | 0.6378 | 0.9478 | 0.1075 | 0.037 (5)* | |
C4 | 0.4459 (2) | 0.98857 (15) | 0.21226 (13) | 0.0305 (4) | |
C5 | 0.4659 (2) | 0.89883 (16) | 0.29428 (13) | 0.0345 (4) | |
H5 | 0.5539 | 0.8439 | 0.2993 | 0.029 (4)* | |
C6 | 0.3268 (2) | 0.90902 (15) | 0.36661 (14) | 0.0380 (4) | |
H6 | 0.3086 | 0.8621 | 0.4274 | 0.045 (5)* | |
C7 | 0.2209 (3) | 1.00325 (15) | 0.32982 (14) | 0.0386 (4) | |
H7 | 0.1213 | 1.0284 | 0.3625 | 0.055 (6)* | |
C8 | 0.2926 (2) | 1.05274 (15) | 0.23482 (14) | 0.0331 (4) | |
H8 | 0.2482 | 1.1154 | 0.1945 | 0.037 (5)* | |
C9 | 0.0850 (3) | 0.8540 (2) | 0.08396 (15) | 0.0484 (5) | |
H9 | 0.0442 | 0.9152 | 0.0403 | 0.074 (8)* | |
C10 | 0.0078 (3) | 0.8105 (2) | 0.18015 (16) | 0.0520 (6) | |
H10 | −0.0922 | 0.8384 | 0.2104 | 0.070 (8)* | |
C11 | 0.1104 (3) | 0.71711 (19) | 0.22152 (17) | 0.0534 (6) | |
H11 | 0.0898 | 0.6733 | 0.2838 | 0.075 (8)* | |
C12 | 0.2490 (3) | 0.70237 (17) | 0.15176 (15) | 0.0525 (5) | |
H12 | 0.3354 | 0.6467 | 0.1597 | 0.078 (8)* | |
C13 | 0.2339 (3) | 0.78766 (17) | 0.06696 (14) | 0.0461 (5) | |
H13 | 0.3092 | 0.7978 | 0.0103 | 0.045 (5)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Fe1 | 0.02772 (17) | 0.02787 (18) | 0.02737 (17) | −0.00143 (12) | −0.00091 (10) | 0.00421 (8) |
O1 | 0.0459 (8) | 0.0394 (7) | 0.0380 (7) | −0.0051 (6) | 0.0095 (5) | 0.0059 (6) |
C1 | 0.0323 (9) | 0.0302 (9) | 0.0383 (9) | −0.0023 (8) | 0.0041 (7) | −0.0050 (9) |
C2 | 0.0274 (8) | 0.0294 (8) | 0.0317 (8) | −0.0017 (7) | 0.0020 (6) | −0.0014 (7) |
C3 | 0.0250 (9) | 0.0292 (9) | 0.0392 (9) | −0.0017 (7) | 0.0000 (7) | 0.0007 (8) |
C4 | 0.0317 (9) | 0.0275 (9) | 0.0322 (9) | −0.0030 (7) | −0.0038 (7) | 0.0034 (7) |
C5 | 0.0341 (10) | 0.0326 (9) | 0.0368 (10) | −0.0032 (8) | −0.0094 (7) | 0.0081 (7) |
C6 | 0.0487 (11) | 0.0353 (10) | 0.0300 (9) | −0.0048 (8) | −0.0020 (8) | 0.0050 (8) |
C7 | 0.0475 (11) | 0.0346 (9) | 0.0337 (9) | 0.0007 (9) | 0.0099 (9) | −0.0001 (7) |
C8 | 0.0396 (11) | 0.0257 (8) | 0.0339 (9) | 0.0029 (7) | 0.0035 (8) | 0.0018 (7) |
C9 | 0.0477 (12) | 0.0633 (13) | 0.0343 (10) | −0.0102 (11) | −0.0129 (9) | 0.0058 (10) |
C10 | 0.0337 (11) | 0.0772 (15) | 0.0451 (11) | −0.0159 (11) | −0.0069 (10) | 0.0045 (11) |
C11 | 0.0604 (15) | 0.0497 (13) | 0.0502 (12) | −0.0287 (11) | −0.0086 (10) | 0.0086 (10) |
C12 | 0.0693 (15) | 0.0318 (9) | 0.0563 (12) | −0.0073 (11) | −0.0093 (13) | −0.0085 (8) |
C13 | 0.0529 (13) | 0.0494 (11) | 0.0362 (10) | −0.0109 (11) | −0.0004 (10) | −0.0087 (8) |
Geometric parameters (Å, º) top
Fe1—C5 | 2.0389 (18) | C5—C6 | 1.426 (3) |
Fe1—C4 | 2.0456 (17) | C5—H5 | 0.9300 |
Fe1—C10 | 2.0469 (19) | C6—C7 | 1.421 (3) |
Fe1—C11 | 2.047 (2) | C6—H6 | 0.9300 |
Fe1—C9 | 2.0556 (18) | C7—C8 | 1.421 (3) |
Fe1—C13 | 2.0534 (17) | C7—H7 | 0.9300 |
Fe1—C8 | 2.0558 (17) | C8—H8 | 0.9300 |
Fe1—C6 | 2.0528 (18) | C9—C13 | 1.408 (3) |
Fe1—C12 | 2.0555 (18) | C9—C10 | 1.427 (3) |
Fe1—C7 | 2.0597 (17) | C9—H9 | 0.9300 |
O1—C1 | 1.220 (2) | C10—C11 | 1.418 (3) |
C1—C2 | 1.446 (2) | C10—H10 | 0.9300 |
C1—H1 | 0.9300 | C11—C12 | 1.408 (3) |
C2—C3 | 1.344 (2) | C11—H11 | 0.9300 |
C2—H2 | 0.9300 | C12—C13 | 1.425 (3) |
C3—C4 | 1.452 (2) | C12—H12 | 0.9300 |
C3—H3 | 0.9300 | C13—H13 | 0.9300 |
C4—C8 | 1.437 (3) | Fe1—Ccp | 2.051 (2) |
C4—C5 | 1.438 (2) | | |
| | | |
C5—Fe1—C4 | 41.21 (6) | C8—C4—Fe1 | 69.87 (10) |
C5—Fe1—C10 | 159.07 (7) | C5—C4—Fe1 | 69.14 (10) |
C4—Fe1—C10 | 158.18 (8) | C3—C4—Fe1 | 124.77 (11) |
C5—Fe1—C11 | 122.71 (8) | C6—C5—C4 | 107.80 (16) |
C4—Fe1—C11 | 160.23 (9) | C6—C5—Fe1 | 70.13 (11) |
C10—Fe1—C11 | 40.52 (10) | C4—C5—Fe1 | 69.64 (10) |
C5—Fe1—C9 | 158.37 (8) | C6—C5—H5 | 126.1 |
C4—Fe1—C9 | 122.80 (7) | C4—C5—H5 | 126.1 |
C10—Fe1—C9 | 40.72 (8) | Fe1—C5—H5 | 125.7 |
C11—Fe1—C9 | 68.23 (9) | C5—C6—C7 | 108.20 (16) |
C5—Fe1—C13 | 122.63 (8) | C5—C6—Fe1 | 69.08 (10) |
C4—Fe1—C13 | 108.79 (7) | C7—C6—Fe1 | 70.05 (10) |
C10—Fe1—C13 | 67.92 (9) | C5—C6—H6 | 125.9 |
C11—Fe1—C13 | 68.03 (8) | C7—C6—H6 | 125.9 |
C9—Fe1—C13 | 40.09 (8) | Fe1—C6—H6 | 126.5 |
C5—Fe1—C8 | 69.02 (7) | C8—C7—C6 | 108.61 (17) |
C4—Fe1—C8 | 41.02 (7) | C8—C7—Fe1 | 69.65 (10) |
C10—Fe1—C8 | 121.91 (9) | C6—C7—Fe1 | 69.53 (10) |
C11—Fe1—C8 | 156.76 (9) | C8—C7—H7 | 125.7 |
C9—Fe1—C8 | 108.53 (8) | C6—C7—H7 | 125.7 |
C13—Fe1—C8 | 125.30 (7) | Fe1—C7—H7 | 126.7 |
C5—Fe1—C6 | 40.79 (7) | C7—C8—C4 | 107.78 (16) |
C4—Fe1—C6 | 68.74 (7) | C7—C8—Fe1 | 69.95 (10) |
C10—Fe1—C6 | 122.79 (8) | C4—C8—Fe1 | 69.11 (9) |
C11—Fe1—C6 | 106.38 (8) | C7—C8—H8 | 126.1 |
C9—Fe1—C6 | 159.98 (8) | C4—C8—H8 | 126.1 |
C13—Fe1—C6 | 157.66 (8) | Fe1—C8—H8 | 126.4 |
C8—Fe1—C6 | 68.36 (7) | C13—C9—C10 | 107.75 (18) |
C5—Fe1—C12 | 107.44 (9) | C13—C9—Fe1 | 69.87 (10) |
C4—Fe1—C12 | 124.77 (8) | C10—C9—Fe1 | 69.32 (10) |
C10—Fe1—C12 | 67.76 (10) | C13—C9—H9 | 126.1 |
C11—Fe1—C12 | 40.15 (9) | C10—C9—H9 | 126.1 |
C9—Fe1—C12 | 67.84 (9) | Fe1—C9—H9 | 126.3 |
C13—Fe1—C12 | 40.58 (8) | C11—C10—C9 | 107.96 (19) |
C8—Fe1—C12 | 161.93 (8) | C11—C10—Fe1 | 69.75 (11) |
C6—Fe1—C12 | 121.30 (8) | C9—C10—Fe1 | 69.97 (10) |
C5—Fe1—C7 | 68.48 (8) | C11—C10—H10 | 126.0 |
C4—Fe1—C7 | 68.46 (7) | C9—C10—H10 | 126.0 |
C10—Fe1—C7 | 107.28 (9) | Fe1—C10—H10 | 125.8 |
C11—Fe1—C7 | 121.04 (8) | C12—C11—C10 | 108.04 (18) |
C9—Fe1—C7 | 124.47 (8) | C12—C11—Fe1 | 70.25 (11) |
C13—Fe1—C7 | 161.13 (8) | C10—C11—Fe1 | 69.73 (12) |
C8—Fe1—C7 | 40.40 (7) | C12—C11—H11 | 126.0 |
C6—Fe1—C7 | 40.43 (7) | C10—C11—H11 | 126.0 |
C12—Fe1—C7 | 156.37 (7) | Fe1—C11—H11 | 125.6 |
O1—C1—C2 | 124.63 (17) | C11—C12—C13 | 108.12 (19) |
O1—C1—H1 | 117.7 | C11—C12—Fe1 | 69.61 (11) |
C2—C1—H1 | 117.7 | C13—C12—Fe1 | 69.63 (10) |
C3—C2—C1 | 121.34 (16) | C11—C12—H12 | 125.9 |
C3—C2—H2 | 119.3 | C13—C12—H12 | 125.9 |
C1—C2—H2 | 119.3 | Fe1—C12—H12 | 126.4 |
C2—C3—C4 | 125.46 (16) | C9—C13—C12 | 108.12 (18) |
C2—C3—H3 | 117.3 | C9—C13—Fe1 | 70.04 (11) |
C4—C3—H3 | 117.3 | C12—C13—Fe1 | 69.79 (10) |
C8—C4—C5 | 107.60 (15) | C9—C13—H13 | 125.9 |
C8—C4—C3 | 126.76 (14) | C12—C13—H13 | 125.9 |
C5—C4—C3 | 125.61 (16) | Fe1—C13—H13 | 125.8 |
Hydrogen-bond geometry (Å, º) top
D—H···A | H···A | D···A | D—H···A |
C2—H2···O1i | 2.55 | 3.609 | 168 |
C8—H8···O1i | 2.31 | 3.369 | 167 |
C5—H5···O1ii | 2.40 | 3.283 | 137 |
C6—H6···O1iii | 2.50 | 3.560 | 168 |
Symmetry codes: (i) x−1/2, −y+5/2, −z; (ii) −x+3/2, −y+2, z+1/2; (iii) −x+1, y−1/2, −z+1/2. |