3-Ferrocenyl­prop-2-enal

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.

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

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Computing details

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

Crystal data

[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) Å^3	Cuboid, red
Z = 4	0.5 × 0.2 × 0.2 mm

Data collection

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

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.017	Only H-atom displacement parameters refined
wR(F^2) = 0.051	w = 1/[σ^2(Fo^2) + (0.0319P)^2 + 0.0364P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	H···A	D···A	D—H···A
C2—H2···O1^i	2.55	3.609	168
C8—H8···O1^i	2.31	3.369	167
C5—H5···O1^ii	2.40	3.283	137
C6—H6···O1^iii	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.