(E)-3-Ferrocenyl-1-(4-tolyl­phen­yl)prop-2-en-1-one

Teng, M.-Y.; Mao, X.-B.; Song, Q.-B.; Tiekink, E.R.T.

doi:10.1107/S1600536806011767

(E)-3-Ferrocenyl-1-(4-tolylphenyl)prop-2-en-1-one

M.-Y. Teng, X.-B. Mao, Q.-B. Song and E. R. T. Tiekink

In the title compound, [Fe(C₅H₅)(C₂₁H₁₇O)], significant conformational differences in the ferrocenyl-C(H)=C(H)C(=O)R groups distinguish the two independent molecules comprising the asymmetric unit. C—H

π interactions appear to influence the crystal packing.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806011767/hb2028sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806011767/hb2028Isup2.hkl Contains datablock I

CCDC reference: 608337

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.006 Å
R factor = 0.041
wR factor = 0.101
Data-to-parameter ratio = 17.7

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT111_ALERT_2_B ADDSYM Detects (Pseudo) Centre of Symmetry .....         85 PerFit
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.72 Ratio
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C9A    -   C10A    ..       9.35 su
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for         C7
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for        C7A
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for        C8A
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for        Fe1
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for       Fe1A

Alert level C
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.99 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.22 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C6
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C8
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for       C10A

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           27.50
           From the CIF: _reflns_number_total               8973
           Count of symmetry unique reflns         4890
           Completeness (_total/calc)            183.50%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      4083
           Fraction of Friedel pairs measured     0.835
           Are heavy atom types Z>Si present        yes

   0 ALERT level A = In general: serious problem
   8 ALERT level B = Potentially serious problem
   7 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  12 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CrystalStructure (Rigaku/MSC, 2004); cell refinement: CrystalStructure; data reduction: CrystalStructure; program(s) used to solve structure: PATTY in DIRDIF92 (Beurskens et al., 1992); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

(E)-3-Ferroceneyl-1-(4-tolylphenyl)prop-2-en-1-one top

Crystal data top

[Fe(C₅H₅)(C₂₁H₁₇O)]	F(000) = 848
M_r = 406.29	D_x = 1.367 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: P 2yb	Cell parameters from 16684 reflections
a = 11.140 (3) Å	θ = 3.2–27.5°
b = 7.518 (2) Å	µ = 0.78 mm⁻¹
c = 24.123 (6) Å	T = 293 K
β = 102.207 (9)°	Block, brown
V = 1974.6 (9) Å³	0.31 × 0.20 × 0.10 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID diffractometer	8973 independent reflections
Radiation source: fine-focus sealed tube	7893 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
Detector resolution: 10.0 pixels mm^-1	θ_max = 27.5°, θ_min = 3.2°
ω scans	h = −14→14
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −9→9
T_min = 0.773, T_max = 0.925	l = −31→29
19618 measured reflections

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)] = 0.041	H-atom parameters constrained
wR(F²) = 0.101	w = 1/[σ²(F_o²) + (0.0357P)² + 1.3096P] where P = (F_o² + 2F_c²)/3
S = 1.09	(Δ/σ)_max = 0.001
8973 reflections	Δρ_max = 0.47 e Å⁻³
508 parameters	Δρ_min = −0.33 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 4106 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.212 (18)

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	U_iso*/U_eq
Fe1	1.06235 (4)	−0.00132 (5)	0.395945 (18)	0.04247 (12)
Fe1A	0.44057 (4)	1.02364 (5)	0.605087 (18)	0.04332 (12)
O1	0.7659 (2)	0.2789 (5)	0.21394 (12)	0.0862 (11)
O1A	0.7182 (2)	0.6292 (5)	0.77947 (11)	0.0886 (11)
C1	1.0775 (3)	0.2138 (5)	0.34666 (14)	0.0451 (7)
C1A	0.4233 (3)	0.7975 (5)	0.64896 (14)	0.0462 (7)
C2	1.1782 (3)	0.0964 (5)	0.34795 (14)	0.0485 (8)
H2	1.1989	0.0420	0.3166	0.058*
C2A	0.3248 (3)	0.9177 (5)	0.65150 (14)	0.0476 (8)
H2A	0.3065	0.9651	0.6844	0.057*
C3	1.2417 (3)	0.0765 (5)	0.40512 (14)	0.0520 (9)
H3	1.3104	0.0056	0.4178	0.062*
C3A	0.2601 (3)	0.9519 (5)	0.59545 (15)	0.0533 (9)
H3A	0.1917	1.0250	0.5851	0.064*
C4	1.1820 (3)	0.1838 (5)	0.43963 (16)	0.0550 (9)
H4	1.2057	0.1979	0.4787	0.066*
C4A	0.3173 (4)	0.8560 (5)	0.55783 (15)	0.0546 (9)
H4A	0.2936	0.8569	0.5185	0.066*
C5	1.0807 (4)	0.2648 (5)	0.40393 (18)	0.0533 (10)
H5	1.0246	0.3397	0.4158	0.064*
C5A	0.4164 (4)	0.7588 (5)	0.58990 (18)	0.0511 (10)
H5A	0.4682	0.6829	0.5754	0.061*
C6	1.0023 (7)	−0.2456 (8)	0.3666 (3)	0.104 (2)
H6	1.0252	−0.3070	0.3370	0.125*
C6A	0.6144 (5)	1.1146 (10)	0.6295 (3)	0.108 (2)
H6A	0.6792	1.0538	0.6522	0.130*
C7A	0.5365 (10)	1.2232 (12)	0.6488 (3)	0.136 (4)
H7A	0.5363	1.2501	0.6864	0.164*
C7	0.9040 (6)	−0.1263 (10)	0.3615 (3)	0.117 (3)
H7	0.8501	−0.0913	0.3284	0.140*
C8	0.9041 (5)	−0.0699 (8)	0.4183 (4)	0.108 (2)
H8	0.8500	0.0097	0.4296	0.129*
C8A	0.4548 (7)	1.2883 (7)	0.5997 (5)	0.129 (4)
H8A	0.3902	1.3673	0.5989	0.155*
C9	0.9994 (5)	−0.1563 (9)	0.4523 (2)	0.0929 (18)
H9	1.0203	−0.1461	0.4916	0.111*
C9A	0.4892 (5)	1.2125 (9)	0.5539 (2)	0.0971 (19)
H9A	0.4525	1.2311	0.5160	0.116*
C10A	0.5853 (6)	1.1068 (9)	0.5735 (3)	0.103 (2)
H10A	0.6257	1.0380	0.5511	0.124*
C10	1.0580 (6)	−0.2562 (7)	0.4218 (3)	0.0864 (17)
H10	1.1274	−0.3240	0.4363	0.104*
C11	0.9779 (3)	0.2538 (5)	0.29865 (16)	0.0515 (9)
H11	0.9074	0.3042	0.3069	0.062*
C11A	0.5188 (3)	0.7371 (5)	0.69531 (15)	0.0504 (8)
H11A	0.5864	0.6827	0.6856	0.060*
C12	0.9777 (3)	0.2257 (5)	0.24441 (15)	0.0517 (8)
H12	1.0494	0.1896	0.2338	0.062*
C12A	0.5204 (3)	0.7509 (5)	0.75025 (15)	0.0496 (8)
H12A	0.4523	0.7972	0.7619	0.059*
C13	0.8645 (3)	0.2513 (5)	0.20092 (15)	0.0552 (9)
C13A	0.6292 (3)	0.6935 (5)	0.79362 (14)	0.0520 (8)
C14	0.8711 (3)	0.2403 (4)	0.14001 (14)	0.0468 (8)
C14A	0.6265 (3)	0.7134 (4)	0.85472 (13)	0.0424 (7)
C15	0.9739 (3)	0.2942 (5)	0.12066 (14)	0.0486 (7)
H15	1.0434	0.3323	0.1465	0.058*
C15A	0.5355 (3)	0.8056 (4)	0.87422 (13)	0.0443 (6)
H15A	0.4725	0.8602	0.8484	0.053*
C16	0.9745 (3)	0.2921 (4)	0.06372 (14)	0.0468 (7)
H16	1.0438	0.3321	0.0517	0.056*
C16A	0.5376 (2)	0.8172 (4)	0.93163 (12)	0.0428 (6)
H16A	0.4769	0.8825	0.9436	0.051*
C17	0.8739 (3)	0.2316 (4)	0.02352 (14)	0.0395 (6)
C17A	0.6289 (3)	0.7331 (4)	0.97234 (13)	0.0366 (6)
C18	0.7726 (2)	0.1726 (4)	0.04375 (13)	0.0476 (7)
H18	0.7049	0.1276	0.0183	0.057*
C18A	0.7203 (2)	0.6422 (4)	0.95163 (12)	0.0436 (6)
H18A	0.7833	0.5865	0.9772	0.052*
C19	0.7703 (2)	0.1793 (4)	0.10027 (13)	0.0508 (7)
H19	0.7002	0.1425	0.1123	0.061*
C19A	0.7194 (2)	0.6333 (4)	0.89465 (12)	0.0460 (6)
H19A	0.7820	0.5726	0.8825	0.055*
C20	0.8761 (3)	0.2271 (4)	−0.03837 (14)	0.0391 (6)
C20A	0.6288 (3)	0.7390 (4)	1.03361 (13)	0.0378 (6)
C21	0.9679 (3)	0.3101 (5)	−0.05944 (14)	0.0489 (7)
H21	1.0309	0.3678	−0.0345	0.059*
C21A	0.5312 (3)	0.8141 (5)	1.05361 (14)	0.0497 (7)
H21A	0.4650	0.8613	1.0278	0.060*
C22	0.9683 (3)	0.3093 (5)	−0.11658 (15)	0.0565 (8)
H22	1.0310	0.3678	−0.1292	0.068*
C22A	0.5309 (3)	0.8198 (5)	1.11078 (14)	0.0563 (8)
H22A	0.4641	0.8698	1.1226	0.068*
C23	0.8780 (4)	0.2238 (5)	−0.15539 (17)	0.0556 (9)
C23A	0.6272 (4)	0.7532 (5)	1.15068 (16)	0.0550 (9)
C24	0.7859 (3)	0.1410 (5)	−0.13471 (15)	0.0601 (8)
H24	0.7231	0.0834	−0.1599	0.072*
C24A	0.7234 (3)	0.6768 (5)	1.13134 (14)	0.0605 (8)
H24A	0.7895	0.6300	1.1574	0.073*
C25	0.7848 (3)	0.1415 (4)	−0.07794 (13)	0.0529 (7)
H25	0.7217	0.0834	−0.0655	0.063*
C25A	0.7237 (3)	0.6684 (4)	1.07439 (13)	0.0505 (7)
H25A	0.7893	0.6138	1.0629	0.061*
C26	0.8795 (5)	0.2216 (8)	−0.21824 (18)	0.0810 (13)
H26A	0.8210	0.1359	−0.2372	0.121*
H26B	0.9601	0.1901	−0.2232	0.121*
H26C	0.8582	0.3374	−0.2341	0.121*
C26A	0.6286 (6)	0.7651 (8)	1.2135 (2)	0.0912 (16)
H26D	0.6219	0.8874	1.2239	0.137*
H26E	0.7042	0.7165	1.2347	0.137*
H26F	0.5607	0.6990	1.2217	0.137*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe1	0.0446 (2)	0.0453 (3)	0.0382 (2)	−0.0046 (2)	0.01040 (18)	0.0025 (2)
Fe1A	0.0470 (2)	0.0432 (3)	0.0398 (2)	−0.0028 (2)	0.00936 (19)	0.0029 (2)
O1	0.0460 (13)	0.156 (3)	0.0603 (16)	0.0197 (17)	0.0193 (12)	0.0196 (18)
O1A	0.0672 (16)	0.147 (3)	0.0554 (14)	0.0510 (19)	0.0215 (12)	0.0206 (18)
C1	0.0522 (18)	0.0425 (17)	0.0423 (17)	−0.0039 (15)	0.0140 (14)	0.0063 (14)
C1A	0.0494 (17)	0.0488 (18)	0.0418 (17)	0.0042 (16)	0.0124 (14)	0.0081 (15)
C2	0.0438 (16)	0.057 (2)	0.0475 (18)	−0.0024 (15)	0.0159 (14)	0.0021 (16)
C2A	0.0448 (17)	0.059 (2)	0.0409 (18)	−0.0016 (16)	0.0130 (14)	0.0011 (15)
C3	0.0417 (16)	0.060 (2)	0.0525 (19)	−0.0026 (15)	0.0062 (15)	0.0101 (17)
C3A	0.0435 (17)	0.059 (2)	0.056 (2)	−0.0033 (16)	0.0069 (16)	0.0022 (17)
C4	0.061 (2)	0.056 (2)	0.0441 (18)	−0.0131 (18)	0.0044 (16)	−0.0019 (16)
C4A	0.067 (2)	0.053 (2)	0.0399 (17)	−0.0070 (18)	0.0012 (16)	−0.0001 (15)
C5	0.070 (3)	0.042 (2)	0.051 (2)	−0.0002 (16)	0.0219 (19)	−0.0031 (14)
C5A	0.063 (2)	0.045 (2)	0.0443 (18)	0.0016 (15)	0.0089 (17)	−0.0038 (14)
C6	0.154 (6)	0.074 (3)	0.092 (4)	−0.060 (4)	0.046 (4)	−0.029 (3)
C6A	0.073 (3)	0.116 (5)	0.118 (5)	−0.044 (3)	−0.018 (3)	0.030 (4)
C7A	0.216 (9)	0.133 (6)	0.078 (3)	−0.125 (6)	0.072 (5)	−0.054 (4)
C7	0.103 (4)	0.121 (5)	0.094 (4)	−0.073 (4)	−0.053 (3)	0.050 (4)
C8	0.052 (2)	0.082 (3)	0.201 (7)	−0.018 (2)	0.056 (4)	−0.003 (4)
C8A	0.113 (5)	0.035 (2)	0.271 (11)	−0.011 (3)	0.111 (7)	−0.005 (4)
C9	0.104 (4)	0.127 (5)	0.058 (2)	−0.054 (4)	0.039 (3)	−0.001 (3)
C9A	0.088 (3)	0.105 (4)	0.089 (4)	−0.033 (3)	0.000 (3)	0.050 (3)
C10A	0.102 (4)	0.108 (5)	0.119 (5)	−0.044 (4)	0.067 (4)	−0.025 (4)
C10	0.092 (4)	0.061 (3)	0.103 (4)	−0.012 (2)	0.014 (3)	0.034 (3)
C11	0.0516 (18)	0.051 (2)	0.053 (2)	0.0069 (14)	0.0143 (15)	0.0122 (14)
C11A	0.0513 (18)	0.0517 (18)	0.0506 (19)	0.0071 (15)	0.0162 (15)	0.0096 (15)
C12	0.0430 (16)	0.063 (2)	0.0498 (18)	0.0051 (15)	0.0111 (14)	0.0137 (16)
C12A	0.0454 (17)	0.056 (2)	0.0490 (18)	0.0110 (14)	0.0146 (14)	0.0098 (14)
C13	0.0451 (17)	0.066 (2)	0.0556 (19)	0.0100 (15)	0.0141 (14)	0.0181 (16)
C13A	0.0458 (16)	0.063 (2)	0.0500 (17)	0.0119 (15)	0.0154 (13)	0.0151 (15)
C14	0.0370 (14)	0.0525 (19)	0.0504 (17)	0.0076 (13)	0.0081 (12)	0.0144 (14)
C14A	0.0356 (13)	0.0442 (16)	0.0476 (16)	0.0028 (13)	0.0090 (12)	0.0082 (14)
C15	0.0358 (14)	0.0532 (18)	0.0537 (17)	−0.0049 (14)	0.0028 (12)	0.0068 (15)
C15A	0.0352 (13)	0.0467 (16)	0.0491 (16)	0.0088 (13)	0.0049 (12)	0.0095 (14)
C16	0.0339 (14)	0.0507 (17)	0.0553 (17)	−0.0049 (13)	0.0083 (12)	0.0073 (14)
C16A	0.0350 (13)	0.0426 (16)	0.0507 (16)	0.0090 (12)	0.0089 (12)	0.0040 (13)
C17	0.0347 (13)	0.0302 (14)	0.0534 (16)	0.0024 (11)	0.0090 (12)	0.0075 (12)
C17A	0.0326 (12)	0.0305 (13)	0.0453 (15)	−0.0033 (10)	0.0052 (11)	0.0020 (11)
C18	0.0313 (12)	0.0515 (17)	0.0569 (17)	−0.0040 (11)	0.0022 (12)	0.0083 (13)
C18A	0.0333 (12)	0.0458 (15)	0.0491 (15)	0.0099 (11)	0.0028 (11)	0.0073 (12)
C19	0.0318 (13)	0.0642 (19)	0.0563 (17)	0.0021 (12)	0.0094 (12)	0.0176 (15)
C19A	0.0321 (12)	0.0543 (16)	0.0519 (16)	0.0083 (12)	0.0099 (11)	0.0050 (13)
C20	0.0338 (13)	0.0299 (14)	0.0530 (16)	0.0046 (11)	0.0081 (12)	0.0085 (12)
C20A	0.0323 (13)	0.0320 (14)	0.0473 (15)	−0.0019 (11)	0.0044 (11)	0.0008 (12)
C21	0.0449 (15)	0.0464 (16)	0.0555 (18)	−0.0045 (14)	0.0108 (13)	0.0041 (14)
C21A	0.0449 (15)	0.0470 (17)	0.0549 (17)	0.0094 (14)	0.0050 (13)	−0.0023 (14)
C22	0.0523 (18)	0.0542 (18)	0.068 (2)	0.0013 (16)	0.0230 (16)	0.0107 (17)
C22A	0.0567 (18)	0.0553 (19)	0.0596 (19)	0.0063 (16)	0.0184 (15)	−0.0088 (16)
C23	0.064 (2)	0.0487 (18)	0.0555 (19)	0.0106 (16)	0.0148 (16)	0.0033 (16)
C23A	0.071 (2)	0.048 (2)	0.0466 (18)	−0.0047 (16)	0.0147 (16)	0.0028 (14)
C24	0.0611 (19)	0.0565 (19)	0.0582 (19)	−0.0070 (16)	0.0026 (15)	−0.0056 (16)
C24A	0.0593 (19)	0.070 (2)	0.0493 (17)	0.0109 (17)	0.0058 (14)	0.0110 (16)
C25	0.0479 (16)	0.0522 (17)	0.0574 (18)	−0.0108 (14)	0.0086 (14)	0.0010 (15)
C25A	0.0437 (15)	0.0567 (18)	0.0521 (16)	0.0110 (13)	0.0123 (13)	0.0099 (14)
C26	0.102 (3)	0.086 (3)	0.057 (2)	0.006 (3)	0.020 (2)	0.008 (2)
C26A	0.120 (4)	0.102 (4)	0.055 (2)	0.013 (3)	0.025 (3)	−0.001 (2)

Geometric parameters (Å, º) top

C13—O1	1.222 (4)	C9—H9	0.9300
C1—C11	1.456 (5)	C9A—C10A	1.337 (8)
C11—C12	1.325 (5)	C9A—H9A	0.9300
C12—C13	1.472 (5)	C10A—H10A	0.9300
C13a—O1a	1.215 (4)	C10—H10	0.9300
C1a—C11a	1.444 (5)	C11—H11	0.9300
C11a—C12a	1.326 (5)	C11A—H11A	0.9300
C12a—C13a	1.488 (5)	C12—H12	0.9300
Fe1—C8	2.016 (4)	C12A—H12A	0.9300
Fe1—C1	2.035 (3)	C13—C14	1.489 (5)
Fe1—C7	2.017 (5)	C13A—C14A	1.488 (5)
Fe1—C6	2.030 (5)	C14—C15	1.386 (4)
Fe1—C5	2.016 (4)	C14—C19	1.391 (5)
Fe1—C4	2.057 (4)	C14A—C19A	1.393 (4)
Fe1—C3	2.048 (3)	C14A—C15A	1.390 (4)
Fe1—C9	2.025 (5)	C15—C16	1.375 (5)
Fe1—C2	2.044 (3)	C15—H15	0.9300
Fe1—C10	2.019 (5)	C15A—C16A	1.383 (4)
Fe1A—C8A	2.002 (6)	C15A—H15A	0.9300
Fe1A—C9A	2.029 (5)	C16—C17	1.394 (4)
Fe1A—C7A	2.007 (5)	C16—H16	0.9300
Fe1A—C3A	2.046 (4)	C16A—C17A	1.406 (4)
Fe1A—C5A	2.032 (4)	C16A—H16A	0.9300
Fe1A—C2A	2.040 (3)	C17—C18	1.393 (4)
Fe1A—C1A	2.033 (4)	C17—C20	1.499 (5)
Fe1A—C4A	2.028 (4)	C17A—C18A	1.403 (4)
Fe1A—C10A	2.022 (5)	C17A—C20A	1.479 (4)
Fe1A—C6A	2.020 (5)	C18—C19	1.370 (4)
C1—C2	1.423 (5)	C18—H18	0.9300
C1—C5	1.427 (5)	C18A—C19A	1.374 (4)
C1A—C5A	1.440 (5)	C18A—H18A	0.9300
C1A—C2A	1.433 (5)	C19—H19	0.9300
C2—C3	1.419 (5)	C19A—H19A	0.9300
C2—H2	0.9300	C20—C25	1.396 (4)
C2A—C3A	1.415 (5)	C20—C21	1.383 (4)
C2A—H2A	0.9300	C20A—C21A	1.398 (4)
C3—C4	1.421 (5)	C20A—C25A	1.388 (4)
C3—H3	0.9300	C21—C22	1.380 (5)
C3A—C4A	1.412 (5)	C21—H21	0.9300
C3A—H3A	0.9300	C21A—C22A	1.380 (5)
C4—C5	1.406 (6)	C21A—H21A	0.9300
C4—H4	0.9300	C22—C23	1.380 (5)
C4A—C5A	1.411 (6)	C22—H22	0.9300
C4A—H4A	0.9300	C22A—C23A	1.375 (5)
C5—H5	0.9300	C22A—H22A	0.9300
C5A—H5A	0.9300	C23—C24	1.381 (5)
C6—C7	1.401 (9)	C23—C26	1.520 (6)
C6—C10	1.348 (9)	C23A—C24A	1.381 (5)
C6—H6	0.9300	C23A—C26A	1.514 (6)
C6A—C10A	1.321 (8)	C24—C25	1.372 (5)
C6A—C7A	1.344 (10)	C24—H24	0.9300
C6A—H6A	0.9300	C24A—C25A	1.376 (4)
C7A—C8A	1.419 (11)	C24A—H24A	0.9300
C7A—H7A	0.9300	C25—H25	0.9300
C7—C8	1.434 (9)	C25A—H25A	0.9300
C7—H7	0.9300	C26—H26A	0.9600
C8—C9	1.361 (8)	C26—H26B	0.9600
C8—H8	0.9300	C26—H26C	0.9600
C8A—C9A	1.369 (10)	C26A—H26D	0.9600
C8A—H8A	0.9300	C26A—H26E	0.9600
C9—C10	1.316 (8)	C26A—H26F	0.9600

C8—Fe1—C1	123.0 (2)	C4A—C5A—Fe1A	69.5 (2)
C8—Fe1—C7	41.7 (3)	C1A—C5A—H5A	126.0
C1—Fe1—C7	107.64 (18)	C4A—C5A—H5A	126.0
C8—Fe1—C6	67.6 (3)	Fe1A—C5A—H5A	126.8
C1—Fe1—C6	125.3 (2)	C7—C6—C10	108.2 (6)
C7—Fe1—C6	40.5 (3)	C7—C6—Fe1	69.2 (3)
C8—Fe1—C5	107.7 (2)	C10—C6—Fe1	70.1 (3)
C1—Fe1—C5	41.24 (15)	C7—C6—H6	125.9
C7—Fe1—C5	124.3 (3)	C10—C6—H6	125.9
C6—Fe1—C5	161.9 (3)	Fe1—C6—H6	126.3
C8—Fe1—C4	123.0 (2)	C10A—C6A—C7A	110.2 (7)
C1—Fe1—C4	68.71 (15)	C10A—C6A—Fe1A	71.0 (3)
C7—Fe1—C4	160.4 (3)	C7A—C6A—Fe1A	70.0 (3)
C6—Fe1—C4	157.0 (3)	C10A—C6A—H6A	124.9
C5—Fe1—C4	40.37 (17)	C7A—C6A—H6A	124.9
C8—Fe1—C3	158.7 (3)	Fe1A—C6A—H6A	125.7
C1—Fe1—C3	68.71 (14)	C6A—C7A—C8A	105.5 (5)
C7—Fe1—C3	157.8 (3)	C6A—C7A—Fe1A	71.0 (3)
C6—Fe1—C3	122.6 (3)	C8A—C7A—Fe1A	69.1 (3)
C5—Fe1—C3	68.26 (17)	C6A—C7A—H7A	127.2
C4—Fe1—C3	40.50 (15)	C8A—C7A—H7A	127.2
C8—Fe1—C9	39.4 (2)	Fe1A—C7A—H7A	124.3
C1—Fe1—C9	158.8 (2)	C6—C7—C8	105.2 (5)
C7—Fe1—C9	67.1 (2)	C6—C7—Fe1	70.3 (3)
C6—Fe1—C9	65.0 (2)	C8—C7—Fe1	69.2 (3)
C5—Fe1—C9	123.3 (2)	C6—C7—H7	127.4
C4—Fe1—C9	108.92 (19)	C8—C7—H7	127.4
C3—Fe1—C9	124.1 (2)	Fe1—C7—H7	124.8
C8—Fe1—C2	159.4 (3)	C9—C8—C7	106.1 (5)
C1—Fe1—C2	40.82 (14)	C9—C8—Fe1	70.6 (3)
C7—Fe1—C2	122.4 (2)	C7—C8—Fe1	69.2 (3)
C6—Fe1—C2	109.2 (2)	C9—C8—H8	126.9
C5—Fe1—C2	68.54 (16)	C7—C8—H8	126.9
C4—Fe1—C2	68.19 (15)	Fe1—C8—H8	124.8
C3—Fe1—C2	40.57 (13)	C9A—C8A—C7A	106.9 (6)
C9—Fe1—C2	159.5 (2)	C9A—C8A—Fe1A	71.2 (3)
C8—Fe1—C10	66.1 (3)	C7A—C8A—Fe1A	69.5 (4)
C1—Fe1—C10	161.0 (2)	C9A—C8A—H8A	126.6
C7—Fe1—C10	67.0 (2)	C7A—C8A—H8A	126.6
C6—Fe1—C10	38.9 (3)	Fe1A—C8A—H8A	124.4
C5—Fe1—C10	157.0 (2)	C8—C9—C10	110.6 (5)
C4—Fe1—C10	122.6 (2)	C8—C9—Fe1	70.0 (3)
C3—Fe1—C10	108.9 (2)	C10—C9—Fe1	70.8 (3)
C9—Fe1—C10	38.0 (2)	C8—C9—H9	124.7
C2—Fe1—C10	125.2 (2)	C10—C9—H9	124.7
C8A—Fe1A—C9A	39.7 (3)	Fe1—C9—H9	126.1
C8A—Fe1A—C7A	41.4 (3)	C8A—C9A—C10A	107.6 (6)
C9A—Fe1A—C7A	67.4 (3)	C8A—C9A—Fe1A	69.1 (3)
C8A—Fe1A—C3A	110.1 (2)	C10A—C9A—Fe1A	70.5 (3)
C9A—Fe1A—C3A	119.8 (2)	C8A—C9A—H9A	126.2
C7A—Fe1A—C3A	131.1 (3)	C10A—C9A—H9A	126.2
C8A—Fe1A—C5A	166.2 (3)	Fe1A—C9A—H9A	125.8
C9A—Fe1A—C5A	128.2 (3)	C6A—C10A—C9A	109.9 (6)
C7A—Fe1A—C5A	149.6 (4)	C6A—C10A—Fe1A	70.8 (3)
C3A—Fe1A—C5A	68.38 (17)	C9A—C10A—Fe1A	71.0 (3)
C8A—Fe1A—C2A	119.4 (2)	C6A—C10A—H10A	125.1
C9A—Fe1A—C2A	152.7 (2)	C9A—C10A—H10A	125.1
C7A—Fe1A—C2A	109.4 (2)	Fe1A—C10A—H10A	124.7
C3A—Fe1A—C2A	40.50 (14)	C6—C10—C9	109.9 (6)
C5A—Fe1A—C2A	68.98 (16)	C6—C10—Fe1	71.0 (3)
C8A—Fe1A—C1A	151.9 (3)	C9—C10—Fe1	71.2 (3)
C9A—Fe1A—C1A	165.6 (3)	C6—C10—H10	125.1
C7A—Fe1A—C1A	116.8 (3)	C9—C10—H10	125.1
C3A—Fe1A—C1A	68.88 (15)	Fe1—C10—H10	124.3
C5A—Fe1A—C1A	41.50 (15)	C12—C11—H11	116.7
C2A—Fe1A—C1A	41.19 (14)	C1—C11—H11	116.7
C8A—Fe1A—C4A	129.4 (3)	C12A—C11A—H11A	116.5
C9A—Fe1A—C4A	109.2 (2)	C1A—C11A—H11A	116.5
C7A—Fe1A—C4A	169.1 (4)	C13—C12—H12	119.8
C3A—Fe1A—C4A	40.54 (15)	C11—C12—H12	119.8
C5A—Fe1A—C4A	40.67 (17)	C11A—C12A—H12A	119.4
C2A—Fe1A—C4A	68.56 (15)	C13A—C12A—H12A	119.4
C1A—Fe1A—C4A	69.24 (15)	C15—C14—C19	117.9 (3)
C8A—Fe1A—C10A	65.7 (3)	C15—C14—C13	122.2 (3)
C9A—Fe1A—C10A	38.5 (2)	C19—C14—C13	119.8 (3)
C7A—Fe1A—C10A	65.7 (3)	C19A—C14A—C15A	118.0 (3)
C3A—Fe1A—C10A	151.8 (2)	C19A—C14A—C13A	118.3 (3)
C5A—Fe1A—C10A	108.7 (2)	C15A—C14A—C13A	123.7 (3)
C2A—Fe1A—C10A	167.0 (3)	C16—C15—C14	120.8 (3)
C1A—Fe1A—C10A	128.7 (3)	C16—C15—H15	119.6
C4A—Fe1A—C10A	118.7 (2)	C14—C15—H15	119.6
C8A—Fe1A—C6A	66.3 (3)	C14A—C15A—C16A	120.8 (3)
C9A—Fe1A—C6A	65.0 (2)	C14A—C15A—H15A	119.6
C7A—Fe1A—C6A	39.0 (3)	C16A—C15A—H15A	119.6
C3A—Fe1A—C6A	168.6 (3)	C15—C16—C17	121.7 (3)
C5A—Fe1A—C6A	117.8 (3)	C15—C16—H16	119.1
C2A—Fe1A—C6A	130.6 (2)	C17—C16—H16	119.1
C1A—Fe1A—C6A	108.8 (2)	C17A—C16A—C15A	121.8 (3)
C4A—Fe1A—C6A	150.2 (3)	C17A—C16A—H16A	119.1
C10A—Fe1A—C6A	38.1 (2)	C15A—C16A—H16A	119.1
C2—C1—C11	127.6 (3)	C16—C17—C18	116.8 (3)
C1—C11—C12	126.5 (4)	C16—C17—C20	121.4 (3)
C11—C12—C13	120.4 (3)	C18—C17—C20	121.8 (3)
O1—C13—C12	121.3 (3)	C16A—C17A—C18A	116.3 (3)
O1—C13—C14	119.8 (3)	C16A—C17A—C20A	122.1 (3)
C12—C13—C14	118.9 (3)	C18A—C17A—C20A	121.6 (3)
C2a—C1a—C11a	127.6 (3)	C19—C18—C17	121.6 (3)
C1a—C11a—C12a	127.0 (3)	C19—C18—H18	119.2
C11a—C12a—C13a	121.2 (3)	C17—C18—H18	119.2
O1a—C13a—C12a	120.6 (3)	C19A—C18A—C17A	121.9 (2)
O1a—C13a—C14a	120.4 (3)	C19A—C18A—H18A	119.1
C12a—C13a—C14a	118.9 (3)	C17A—C18A—H18A	119.1
C2—C1—C5	106.7 (3)	C18—C19—C14	121.0 (3)
C11—C1—C5	125.0 (4)	C18—C19—H19	119.5
C2—C1—Fe1	69.9 (2)	C14—C19—H19	119.5
C11—C1—Fe1	119.1 (3)	C14A—C19A—C18A	121.2 (3)
C5—C1—Fe1	68.7 (2)	C14A—C19A—H19A	119.4
C5A—C1A—C11A	125.4 (4)	C18A—C19A—H19A	119.4
C5A—C1A—C2A	106.8 (3)	C25—C20—C21	116.4 (3)
C5A—C1A—Fe1A	69.2 (2)	C25—C20—C17	121.9 (3)
C11A—C1A—Fe1A	122.1 (3)	C21—C20—C17	121.6 (3)
C2A—C1A—Fe1A	69.7 (2)	C21A—C20A—C25A	116.1 (3)
C1—C2—C3	108.4 (3)	C21A—C20A—C17A	121.5 (3)
C1—C2—Fe1	69.26 (18)	C25A—C20A—C17A	122.4 (3)
C3—C2—Fe1	69.89 (19)	C20—C21—C22	121.6 (3)
C1—C2—H2	125.8	C20—C21—H21	119.2
C3—C2—H2	125.8	C22—C21—H21	119.2
Fe1—C2—H2	126.6	C20A—C21A—C22A	121.6 (3)
C3A—C2A—C1A	108.2 (3)	C20A—C21A—H21A	119.2
C3A—C2A—Fe1A	70.0 (2)	C22A—C21A—H21A	119.2
C1A—C2A—Fe1A	69.13 (19)	C21—C22—C23	121.6 (3)
C3A—C2A—H2A	125.9	C21—C22—H22	119.2
C1A—C2A—H2A	125.9	C23—C22—H22	119.2
Fe1A—C2A—H2A	126.6	C23A—C22A—C21A	121.4 (3)
C4—C3—C2	108.1 (3)	C23A—C22A—H22A	119.3
C4—C3—Fe1	70.1 (2)	C21A—C22A—H22A	119.3
C2—C3—Fe1	69.55 (19)	C24—C23—C22	117.1 (3)
C4—C3—H3	125.9	C24—C23—C26	121.4 (4)
C2—C3—H3	125.9	C22—C23—C26	121.5 (4)
Fe1—C3—H3	126.0	C22A—C23A—C24A	117.5 (3)
C2A—C3A—C4A	108.3 (3)	C22A—C23A—C26A	121.4 (4)
C2A—C3A—Fe1A	69.52 (19)	C24A—C23A—C26A	121.2 (4)
C4A—C3A—Fe1A	69.0 (2)	C23—C24—C25	121.5 (3)
C2A—C3A—H3A	125.8	C23—C24—H24	119.2
C4A—C3A—H3A	125.8	C25—C24—H24	119.2
Fe1A—C3A—H3A	127.2	C25A—C24A—C23A	121.5 (3)
C5—C4—C3	107.6 (3)	C25A—C24A—H24A	119.3
C5—C4—Fe1	68.3 (2)	C23A—C24A—H24A	119.3
C3—C4—Fe1	69.4 (2)	C20—C25—C24	121.7 (3)
C5—C4—H4	126.2	C20—C25—H25	119.1
C3—C4—H4	126.2	C24—C25—H25	119.1
Fe1—C4—H4	127.6	C24A—C25A—C20A	121.9 (3)
C5A—C4A—C3A	108.6 (3)	C24A—C25A—H25A	119.1
C5A—C4A—Fe1A	69.8 (2)	C20A—C25A—H25A	119.1
C3A—C4A—Fe1A	70.4 (2)	C23—C26—H26A	109.5
C5A—C4A—H4A	125.7	C23—C26—H26B	109.5
C3A—C4A—H4A	125.7	H26A—C26—H26B	109.5
Fe1A—C4A—H4A	125.6	C23—C26—H26C	109.5
C4—C5—C1	109.2 (4)	H26A—C26—H26C	109.5
C4—C5—Fe1	71.4 (2)	H26B—C26—H26C	109.5
C1—C5—Fe1	70.1 (2)	C23A—C26A—H26D	109.5
C4—C5—H5	125.4	C23A—C26A—H26E	109.5
C1—C5—H5	125.4	H26D—C26A—H26E	109.5
Fe1—C5—H5	124.7	C23A—C26A—H26F	109.5
C1A—C5A—C4A	108.0 (3)	H26D—C26A—H26F	109.5
C1A—C5A—Fe1A	69.3 (2)	H26E—C26A—H26F	109.5

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(E)-3-Ferrocenyl-1-(4-tolyl­phen­yl)prop-2-en-1-one

Supporting information

Key indicators

checkCIF/PLATON results

(E)-3-Ferrocenyl-1-(4-tolylphenyl)prop-2-en-1-one