Crystal structure of (E)-1,2-diferrocenyl-1,2-bis(furan-2-yl)ethene

The title compound is the product of a new synthetic route towards tetra­aryl/hetaryl-substituted ethenes that reduces the occurrence of side-products. In the crystal, the mol­ecule is centrosymmetric and the cyclo­penta­dienyl rings are nearly coplanar and aligned slightly closer to a staggered conformation than to an eclipsed one.

Key indicators

• Single-crystal X-ray study
• T = 160 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.032
• wR factor = 0.077
• Data-to-parameter ratio = 19.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for   C4       --C5        .        5.6 s.u.

Alert level G
PLAT398_ALERT_2_G Deviating  C-O-C    Angle From 120 for O1             106.3 Degree
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        254 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         14 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   1 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   4 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 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
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: CrysAlis PRO (Rigaku OD, 2015); cell refinement: CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: ORTEPII (Johnson, 1976) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015b), PLATON (Spek, 2015) and publCIF (Westrip, 2010).

(E)-1,2-Diferrocenyl-1,2-bis(furan-2-yl)ethene

Crystal data

[Fe2(C5H5)2(C20H14O2)]	F(000) = 544
Mr = 528.19	Dx = 1.587 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 5.81006 (13) Å	Cell parameters from 7365 reflections
b = 22.7138 (5) Å	θ = 3.0–29.9°
c = 8.38031 (18) Å	µ = 1.34 mm^−1
β = 91.785 (2)°	T = 160 K
V = 1105.40 (4) Å^3	Tablet, orange
Z = 2	0.20 × 0.16 × 0.08 mm

Data collection

Oxford Diffraction SuperNova, dual radiation diffractometer	3021 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2612 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.026
Detector resolution: 10.3801 pixels mm^-1	θmax = 30.2°, θmin = 2.6°
ω scans	h = −8→7
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2015)	k = −31→31
Tmin = 0.895, Tmax = 1.000	l = −11→11
13881 measured reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.032	H-atom parameters constrained
wR(F^2) = 0.077	w = 1/[σ^2(Fo^2) + (0.0291P)^2 + 0.9916P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.001
3021 reflections	Δρmax = 0.49 e Å^−3
154 parameters	Δρmin = −0.36 e Å^−3

Special details

Experimental. Data collection and full structure determination done by Prof. Anthony Linden: [e-mail]

Solvent used: hexane / dichloromethane Cooling Device: Oxford Instruments Cryojet XL Crystal mount: on a glass fibre Frames collected: 1290 Seconds exposure per frame: 10.0 Degrees rotation per frame: 1602.0 Crystal-detector distance (mm): 55.0

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Fe1	0.46176 (4)	0.65950 (2)	0.41357 (3)	0.01767 (8)
O1	0.5980 (2)	0.54191 (6)	0.79034 (16)	0.0295 (3)
C1	0.5597 (3)	0.52572 (7)	0.5053 (2)	0.0159 (3)
C2	0.7063 (3)	0.53842 (7)	0.6485 (2)	0.0187 (3)
C3	0.7668 (5)	0.55207 (10)	0.9050 (3)	0.0408 (6)
H3	0.7408	0.5562	1.0158	0.049*
C4	0.9717 (4)	0.55529 (10)	0.8395 (3)	0.0418 (6)
H4	1.1150	0.5624	0.8938	0.050*
C5	0.9354 (3)	0.54589 (8)	0.6699 (2)	0.0256 (4)
H5	1.0487	0.5451	0.5906	0.031*
C6	0.5501 (3)	0.57204 (7)	0.38168 (19)	0.0168 (3)
C7	0.7351 (3)	0.61094 (7)	0.3435 (2)	0.0212 (3)
H7	0.8841	0.6111	0.3937	0.025*
C8	0.6590 (4)	0.64909 (8)	0.2187 (2)	0.0264 (4)
H8	0.7483	0.6788	0.1701	0.032*
C9	0.4265 (4)	0.63519 (8)	0.1791 (2)	0.0262 (4)
H9	0.3324	0.6541	0.0998	0.031*
C10	0.3583 (3)	0.58793 (7)	0.2787 (2)	0.0200 (3)
H10	0.2106	0.5700	0.2772	0.024*
C11	0.4528 (4)	0.68024 (9)	0.6520 (2)	0.0295 (4)
H11	0.5075	0.6563	0.7382	0.035*
C12	0.5838 (3)	0.72260 (9)	0.5685 (2)	0.0310 (4)
H12	0.7412	0.7320	0.5891	0.037*
C13	0.4377 (4)	0.74812 (8)	0.4493 (2)	0.0286 (4)
H13	0.4798	0.7778	0.3758	0.034*
C14	0.2176 (3)	0.72175 (8)	0.4587 (2)	0.0267 (4)
H14	0.0866	0.7305	0.3922	0.032*
C15	0.2268 (3)	0.68009 (8)	0.5840 (2)	0.0268 (4)
H15	0.1028	0.6562	0.6169	0.032*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe1	0.02204 (13)	0.01261 (12)	0.01843 (13)	0.00067 (9)	0.00192 (9)	−0.00138 (9)
O1	0.0359 (8)	0.0287 (7)	0.0239 (7)	0.0074 (6)	0.0035 (6)	−0.0018 (6)
C1	0.0146 (7)	0.0145 (7)	0.0186 (8)	0.0026 (6)	0.0019 (6)	−0.0016 (6)
C2	0.0225 (8)	0.0125 (7)	0.0211 (8)	0.0001 (6)	0.0004 (6)	−0.0008 (6)
C3	0.0646 (16)	0.0329 (11)	0.0242 (10)	0.0080 (11)	−0.0104 (10)	−0.0070 (9)
C4	0.0466 (13)	0.0289 (11)	0.0480 (13)	−0.0068 (10)	−0.0295 (11)	0.0027 (10)
C5	0.0207 (8)	0.0236 (9)	0.0324 (10)	−0.0016 (7)	−0.0022 (7)	0.0050 (8)
C6	0.0192 (8)	0.0130 (7)	0.0184 (8)	0.0008 (6)	0.0028 (6)	−0.0025 (6)
C7	0.0214 (8)	0.0167 (8)	0.0260 (9)	0.0003 (6)	0.0064 (7)	−0.0014 (7)
C8	0.0377 (10)	0.0189 (8)	0.0233 (9)	−0.0002 (7)	0.0127 (8)	0.0012 (7)
C9	0.0414 (11)	0.0192 (8)	0.0179 (8)	0.0057 (8)	−0.0011 (7)	−0.0012 (7)
C10	0.0242 (8)	0.0153 (8)	0.0204 (8)	0.0020 (6)	−0.0022 (7)	−0.0037 (6)
C11	0.0464 (12)	0.0227 (9)	0.0193 (8)	0.0082 (8)	−0.0015 (8)	−0.0057 (7)
C12	0.0278 (10)	0.0274 (10)	0.0378 (11)	−0.0027 (8)	0.0019 (8)	−0.0172 (8)
C13	0.0407 (11)	0.0133 (8)	0.0324 (10)	0.0001 (7)	0.0121 (8)	−0.0032 (7)
C14	0.0282 (9)	0.0233 (9)	0.0285 (9)	0.0079 (7)	0.0006 (8)	−0.0050 (7)
C15	0.0326 (10)	0.0219 (9)	0.0267 (9)	−0.0035 (7)	0.0116 (8)	−0.0063 (7)

Geometric parameters (Å, º)

Fe1—C7	2.0352 (17)	C5—H5	0.9500
Fe1—C8	2.0380 (18)	C6—C10	1.434 (2)
Fe1—C13	2.0404 (18)	C6—C7	1.435 (2)
Fe1—C9	2.0456 (18)	C7—C8	1.419 (3)
Fe1—C12	2.0457 (19)	C7—H7	0.9500
Fe1—C14	2.0465 (18)	C8—C9	1.417 (3)
Fe1—C11	2.0555 (19)	C8—H8	0.9500
Fe1—C10	2.0591 (17)	C9—C10	1.424 (3)
Fe1—C15	2.0605 (18)	C9—H9	0.9500
Fe1—C6	2.0712 (16)	C10—H10	0.9500
O1—C2	1.365 (2)	C11—C15	1.415 (3)
O1—C3	1.371 (3)	C11—C12	1.424 (3)
C1—C1^i	1.360 (3)	C11—H11	0.9500
C1—C6	1.476 (2)	C12—C13	1.415 (3)
C1—C2	1.478 (2)	C12—H12	0.9500
C2—C5	1.349 (2)	C13—C14	1.416 (3)
C3—C4	1.329 (4)	C13—H13	0.9500
C3—H3	0.9500	C14—C15	1.414 (3)
C4—C5	1.446 (3)	C14—H14	0.9500
C4—H4	0.9500	C15—H15	0.9500
C7—Fe1—C8	40.77 (7)	C10—C6—C7	106.52 (15)
C7—Fe1—C13	129.40 (8)	C10—C6—C1	127.83 (15)
C8—Fe1—C13	105.96 (8)	C7—C6—C1	125.64 (15)
C7—Fe1—C9	68.43 (8)	C10—C6—Fe1	69.23 (9)
C8—Fe1—C9	40.59 (8)	C7—C6—Fe1	68.20 (9)
C13—Fe1—C9	113.70 (8)	C1—C6—Fe1	126.65 (11)
C7—Fe1—C12	107.73 (8)	C8—C7—C6	108.76 (16)
C8—Fe1—C12	113.42 (8)	C8—C7—Fe1	69.73 (10)
C13—Fe1—C12	40.51 (8)	C6—C7—Fe1	70.89 (9)
C9—Fe1—C12	145.21 (8)	C8—C7—H7	125.6
C7—Fe1—C14	168.36 (8)	C6—C7—H7	125.6
C8—Fe1—C14	129.68 (8)	Fe1—C7—H7	125.3
C13—Fe1—C14	40.56 (8)	C9—C8—C7	108.05 (16)
C9—Fe1—C14	108.34 (8)	C9—C8—Fe1	69.99 (11)
C12—Fe1—C14	68.12 (8)	C7—C8—Fe1	69.51 (10)
C7—Fe1—C11	116.63 (8)	C9—C8—H8	126.0
C8—Fe1—C11	146.90 (9)	C7—C8—H8	126.0
C13—Fe1—C11	68.12 (8)	Fe1—C8—H8	126.1
C9—Fe1—C11	172.39 (9)	C8—C9—C10	108.15 (16)
C12—Fe1—C11	40.64 (8)	C8—C9—Fe1	69.42 (10)
C14—Fe1—C11	67.88 (8)	C10—C9—Fe1	70.22 (10)
C7—Fe1—C10	68.35 (7)	C8—C9—H9	125.9
C8—Fe1—C10	68.30 (7)	C10—C9—H9	125.9
C13—Fe1—C10	147.05 (8)	Fe1—C9—H9	126.0
C9—Fe1—C10	40.58 (7)	C9—C10—C6	108.50 (16)
C12—Fe1—C10	172.33 (8)	C9—C10—Fe1	69.20 (10)
C14—Fe1—C10	117.03 (7)	C6—C10—Fe1	70.13 (9)
C11—Fe1—C10	134.35 (8)	C9—C10—H10	125.8
C7—Fe1—C15	149.65 (8)	C6—C10—H10	125.8
C8—Fe1—C15	169.52 (8)	Fe1—C10—H10	126.5
C13—Fe1—C15	67.94 (8)	C15—C11—C12	107.88 (18)
C9—Fe1—C15	132.74 (8)	C15—C11—Fe1	70.08 (11)
C12—Fe1—C15	67.98 (8)	C12—C11—Fe1	69.31 (11)
C14—Fe1—C15	40.27 (8)	C15—C11—H11	126.1
C11—Fe1—C15	40.22 (8)	C12—C11—H11	126.1
C10—Fe1—C15	111.80 (8)	Fe1—C11—H11	126.1
C7—Fe1—C6	40.91 (7)	C13—C12—C11	107.82 (18)
C8—Fe1—C6	68.75 (7)	C13—C12—Fe1	69.54 (11)
C13—Fe1—C6	169.58 (8)	C11—C12—Fe1	70.05 (11)
C9—Fe1—C6	68.58 (7)	C13—C12—H12	126.1
C12—Fe1—C6	132.19 (8)	C11—C12—H12	126.1
C14—Fe1—C6	149.60 (7)	Fe1—C12—H12	125.9
C11—Fe1—C6	111.05 (7)	C12—C13—C14	108.09 (17)
C10—Fe1—C6	40.64 (6)	C12—C13—Fe1	69.94 (11)
C15—Fe1—C6	118.64 (7)	C14—C13—Fe1	69.95 (11)
C2—O1—C3	106.35 (17)	C12—C13—H13	126.0
C1^i—C1—C6	123.93 (19)	C14—C13—H13	126.0
C1^i—C1—C2	120.04 (19)	Fe1—C13—H13	125.7
C6—C1—C2	116.02 (14)	C15—C14—C13	108.12 (17)
C5—C2—O1	110.90 (16)	C15—C14—Fe1	70.40 (11)
C5—C2—C1	132.40 (16)	C13—C14—Fe1	69.49 (11)
O1—C2—C1	116.67 (15)	C15—C14—H14	125.9
C4—C3—O1	110.49 (19)	C13—C14—H14	125.9
C4—C3—H3	124.8	Fe1—C14—H14	125.7
O1—C3—H3	124.8	C14—C15—C11	108.10 (17)
C3—C4—C5	107.03 (18)	C14—C15—Fe1	69.33 (10)
C3—C4—H4	126.5	C11—C15—Fe1	69.70 (11)
C5—C4—H4	126.5	C14—C15—H15	126.0
C2—C5—C4	105.22 (18)	C11—C15—H15	126.0
C2—C5—H5	127.4	Fe1—C15—H15	126.6
C4—C5—H5	127.4
C3—O1—C2—C5	0.1 (2)	Fe1—C8—C9—C10	−59.76 (12)
C3—O1—C2—C1	178.20 (15)	C7—C8—C9—Fe1	59.30 (12)
C1^i—C1—C2—C5	115.8 (2)	C8—C9—C10—C6	0.0 (2)
C6—C1—C2—C5	−65.4 (2)	Fe1—C9—C10—C6	−59.30 (12)
C1^i—C1—C2—O1	−61.8 (2)	C8—C9—C10—Fe1	59.26 (13)
C6—C1—C2—O1	117.02 (16)	C7—C6—C10—C9	0.52 (19)
C2—O1—C3—C4	0.4 (2)	C1—C6—C10—C9	179.64 (16)
O1—C3—C4—C5	−0.7 (3)	Fe1—C6—C10—C9	58.72 (12)
O1—C2—C5—C4	−0.5 (2)	C7—C6—C10—Fe1	−58.21 (11)
C1—C2—C5—C4	−178.21 (18)	C1—C6—C10—Fe1	120.92 (17)
C3—C4—C5—C2	0.7 (2)	C15—C11—C12—C13	−0.2 (2)
C1^i—C1—C6—C10	32.9 (3)	Fe1—C11—C12—C13	59.52 (13)
C2—C1—C6—C10	−145.89 (16)	C15—C11—C12—Fe1	−59.70 (13)
C1^i—C1—C6—C7	−148.2 (2)	C11—C12—C13—C14	−0.1 (2)
C2—C1—C6—C7	33.1 (2)	Fe1—C12—C13—C14	59.79 (13)
C1^i—C1—C6—Fe1	123.9 (2)	C11—C12—C13—Fe1	−59.84 (13)
C2—C1—C6—Fe1	−54.85 (19)	C12—C13—C14—C15	0.3 (2)
C10—C6—C7—C8	−0.81 (19)	Fe1—C13—C14—C15	60.05 (13)
C1—C6—C7—C8	−179.96 (15)	C12—C13—C14—Fe1	−59.78 (13)
Fe1—C6—C7—C8	−59.67 (12)	C13—C14—C15—C11	−0.4 (2)
C10—C6—C7—Fe1	58.86 (11)	Fe1—C14—C15—C11	59.11 (13)
C1—C6—C7—Fe1	−120.29 (16)	C13—C14—C15—Fe1	−59.48 (13)
C6—C7—C8—C9	0.8 (2)	C12—C11—C15—C14	0.3 (2)
Fe1—C7—C8—C9	−59.60 (13)	Fe1—C11—C15—C14	−58.88 (13)
C6—C7—C8—Fe1	60.40 (12)	C12—C11—C15—Fe1	59.22 (13)
C7—C8—C9—C10	−0.5 (2)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

Cg1, Cg2 and Cg3 are the centroids of the C6–C10, C11–C15 and C2/O1/C3–C5 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···Cg1^ii	0.95	2.81	3.686 (3)	153
C8—H8···Cg2^iii	0.95	2.85	3.764 (2)	161
C10—H10···Cg3^i	0.95	2.68	3.2097 (18)	116

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, y, z+1; (iii) x+1/2, −y+3/2, z−1/2.