A second ortho­rhom­bic polymorph of 3-ferro­cenylacrylaldehyde

Shelukho, E.R.; Zaytsev, V.P.; Khrustalev, V.N.; Hökelek, T.; Belay, A.N.; Hasanov, K.I.; Guliyeva, N.A.

doi:10.1107/S2056989026008170

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ISSN: 2056-9890

Volume 82| Part 9| September 2026| Pages 1048-1051

https://doi.org/10.1107/S2056989026008170

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A second orthorhombic polymorph of 3-ferrocenylacrylaldehyde

Evgeniya R. Shelukho,^a Vladimir P. Zaytsev,^a Victor N. Khrustalev,^a,^b Tuncer Hökelek,^c Alebel N. Belay,^d ^* Khudayar I. Hasanov ^e and Narmina A. Guliyeva ^f

^aRUDN University, 6 Miklukho-Maklaya St., Moscow 117198, Russian Federation, ^bZelinsky Institute of Organic Chemistry of RAS, Leninsky Prospect 47, Moscow 119991, Russian Federation, ^cHacettepe University, Department of Physics, 06800 Beytepe-Ankara, Türkiye, ^dDepartment of Chemistry, Bahir Dar University, PO Box 79, Bahir Dar, Ethiopia, ^eScientific Research Centre (SRC), Azerbaijan Medical University, A. Kasumzade St. 14, AZ 1022, Baku, Azerbaijan, and ^fDepartment of Chemical Engineering, Baku Engineering University, Hasan Aliyev str. 120, AZ0101, Khirdalan, Absheron, Azerbaijan
^*Correspondence e-mail: [email protected]

Edited by W. T. A. Harrison, University of Aberdeen, United Kingdom (Received 21 July 2026; accepted 7 August 2026; online 14 August 2026)

The title compound (systematic name: 3-ferrocenylprop-2-en-1-one), [Fe(C₅H₅)(C₈H₇O)] (I), crystallizing in the space group P2₁2₁2₁, with a = 5.77599 (11) Å, b = 7.38297 (13) Å and c = 24.4180 (4) Å consists of fused ferrocene and acrylaldehyde moieties. In the crystal, C—H⋯O hydrogen bonds link the molecules into infinite chains propagating along the a-axis direction and C—H⋯π interactions help to consolidate the packing. Compound (I) is a polymorph of the previously reported form of ferrocenylacrylaldehyde [Imhof (2004 ). Acta Cryst. E60, m1234–m1236], which also crystallizes in space group P2₁2₁2₁ with cell parameters a = 7.9192 (2) Å, b = 11.1648 (3) Å and c = 12.4204 (4) Å. The Hirshfeld surface analysis of (I) indicates that the most important contributions to the crystal packing are from H⋯ (58.9%), H⋯C/C⋯H (22.6%) and H⋯O/O⋯H (17.5%) contacts. Computational methods revealed a C—H⋯O hydrogen-bonding energy of −10.9 kJ mol⁻¹.

Keywords: ferrocene derivatives; crystal structure; weak interactions.

CCDC reference: 2579562

1. Chemical context

Ferrocene is the trivial name for bis(η⁵-cyclopentadienyl)iron(II), Fe(C₅H₅)₂, a prototypical metallocene comprising an iron atom sandwiched between two parallel negatively charged cyclopentadienyl rings, which was first discovered and characterized at the beginning of the 1950s almost simultaneously by two scientific groups independently of each other (Kealy & Pauson, 1951 ; Miller et al., 1952 ). The discovery of ferrocene more than seventy years ago has significantly influenced chemical research and provided a key impetus for establishing and rapidly expanding organometallic chemistry, which has continued at a rapid pace until now (Štěpnička, 2022 ). Over years of systematic study, ferrocene has proven to be an extraordinarily flexible core structure, with demonstrated value in asymmetric catalysis (Cunningham et al., 2020 ), functional materials (Woo et al., 2021 ), and medicinal (Sharma et al., 2025 ) and analytical chemistry as well as many other research fields. Its success is underpinned by a rare synergy of stability, synthetic versatility, well-defined steric bulk, and electrochemically responsive redox properties that are readily adjustable to target requirements. Recent studies have demonstrated that ferrocene core, functionalized with various organic molecules linkers, can poses anticancer activity against breast cancer (Mbaba et al., 2020 ; Ashgar et al., 2022 ), against lung cancer (Mazur et al., 2022 ) and against leukaemia cell lines such as acute myeloid leukaemia and chronic lymphocytic leukaemia, demonstrating significant cytotoxicity and growth inhibition (Daum et al., 2025 ; Tsypysheva et al., 2020 ). As part of our studies in this area, we now report the synthesis and structure of the title compound, Fe(C₅H₅)(C₈H₇O) (I). It is a polymorph of the structure reported by Imhof (2004) in the same space group with a = 7.9192 (2) Å, b = 11.1648 (3) Å and c = 12.4204 (4) Å [Cambridge Structural Database (Groom et al., 2016 ) refcode YAFVUX], which was crystallized from diethyl ether solution.

2. Structural commentary

Compound (I) consists of a ferrocene core with an attached acrylaldehyde group (Fig. 1). The centroid–centroid distance between the C1–C5 (Cg1) and C6–C10 (Cg2) cyclopentadienyl rings is 3.2990 (17) Å [dihedral angle = 1.84 (16)° and slippage = 0.066 Å], which are almost eclipsed. The iron atom is almost equidistant between the rings [Fe1⋯Cg1 = 1.6455 (12) Å; Fe1⋯Cg2 = 1.6536 (14) Å; Cg1⋯Fe1⋯Cg2 = 178.40 (7)°]. The acrylaldehyde side chain is almost planar (r.m.s. deviation = 0.022 Å), where the O1—C13—C12—C11 and C1—C11—C12—C13 torsion angles are 176.8 (3) and −177.7 (2)°, respectively. The O atom of the aldehyde moiety is in an s-trans conformation with respect to the central C12—C13 single bond, and the C11=C12 [1.341 (4) Å] double bond is slightly elongated with respect to a typical C=C double bond length. The double [C1=O13 = 1.224 (4) Å and C11=C12] bonds lie on opposite sides of the central single [C12—C13 = 1.452 (4) Å] bond, forming a zigzag orientation, presumably minimizing steric hindrance. The C11—C12—C13 [120.2 (3)°] and C2—C1—C11 [124.7 (3)°] bond angles are significantly narrowed while the C1—C11—C12 [126.8 (3)°] and C5—C1—C11 [127.7 (2)°] bond angles are significantly enlarged with respect to the corresponding values [121.34 (16), 125.61 (16), 125.46 (16) and 126.76 (14)°, respectively] in the first polymorph of 3-ferrocenylprop-2-enal (Imhof, 2004).

Figure 1
The molecular structure of (I) with 50% probability ellipsoids.

3. Supramolecular features

In the extended structure of (I), C—H⋯O hydrogen bonds (Table 1) link the molecules into infinite chains propagating along the a-axis direction (Fig. 2) and weak C—H⋯π interactions help to consolidate the crystal packing.

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C6–C10 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O1ⁱ	0.95	2.46	3.252 (3)	141
C8—H8⋯Cg2ⁱⁱ	0.95	2.82	3.736 (3)	161
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]$ ; (ii) $[x+{\script{3\over 2}}, -y-{\script{1\over 2}}, -z]$ .

Figure 2
A partial packing diagram of (I) viewed down the b-axis direction with C—H⋯O hydrogen bonds shown as dashed lines. H atoms not involved in hydrogen bonds are omitted for clarity.

The intermolecular interactions in the crystal were visualized by carrying out a Hirshfeld surface (HS) analysis using CrystalExplorer 17.5 (Spackman et al., 2021 ). Fig. 3 shows the Hirshfeld surface mapped over d_norm. The red spots indicate their roles as the respective donors and/or acceptors atoms in hydrogen bonding, as discussed above. The overall two-dimensional fingerprint plot is shown in Fig. 4a and those delineated into the different contact types are illustrated in Fig. 4b–f. According to the fingerprint plots, the H⋯H, H⋯C/C⋯H and H⋯O/O⋯H contacts make the most significant contributions to the HS, at 58.9%, 22.6% and 17.5%, respectively (Fig. 6).

Figure 3
View of the three-dimensional Hirshfeld surface for (I) plotted over d_norm in the range −0.18 to 1.25 a.u.

Figure 4
The two-dimensional fingerprint plots for (I), showing (a) all interactions, and delineated into (b)–(f) the various contact types.

A void analysis was performed to check the cohesion of the crystal. The volume of the crystal voids and the percentage of free space in the unit cell of (I) are 79.1 Å³ and 7.6%, respectively. These values compare with 126.0 Å³ and 11.5% in YAFVUX, which suggests that (I) is the more stable polymorph. This is supported by the difference in unit-cell volumes [1041.28 (3) Å for (I) and 1098.17 (5) Å for YAFVUX], although it should be note that the intensity data for (I) were collected at 100 K and those for YAFVUX at 183 K.

The intermolecular interaction energies were calculated using the CE–B3LYP/6–31G(d,p) energy model available in CrystalExplorer 17.5 (Spackman et al., 2021), where a cluster of molecules is generated by applying crystallographic symmetry operations with respect to a selected central molecule within the radius of 3.8 Å by default. The total intermolecular energy (E_tot) is the sum of electrostatic (E_ele), polarization (E_pol), dispersion (E_dis) and exchange-repulsion (E_rep) energies (Turner et al., 2015 ) with scale factors of 1.057, 0.740, 0.871 and 0.618, respectively (Mackenzie et al., 2017 ). Interaction energies (in kJ mol⁻¹) for (I) were calculated to be −2.0 (E_ele), −0.7 (E_pol), −16.2 (E_dis), 9.4 (E_rep) and −10.9 (E_tot) for the C6—H6⋯O1 hydrogen bond.

4. Synthesis and crystallization

Ferrocene (1.86 g, 10 mmol) was dissolved in tetrahydrofuran (THF) (30 ml) and cooled to 203 K under an argon atmosphere. A solution of tert-BuLi in pentane (17 mmol, 10 ml) was added to the reaction mixture dropwise under an Ar atmosphere and was stirred for 30 min. Then, 3-(dimethylamino)acrolein (2.0 ml, 20 mmol) was added dropwise (Fig. 5). After that, the mixture was diluted to 10% aq. solution HCl, stirred at 278 K for 30 min and extracted with dichloromethane (DCM) (3 × 30 ml). The combined organic layers were dried over anhydrous Na₂SO₄ and filtered. The organic solvent was evaporated and the target product was purified by column chromatography (SiO₂, 20 × 1.5 cm, eluent: EtOAc/hexane = 1/20); yield 52%, 1.248 g (5.2 mmol), m.p. 363–364 K. Single crystals of (I) in the form of red plates were grown from a solvent mixture of ethyl acetate and hexane at room temperature. ¹H NMR (600.2 MHz, CDCl₃) (J, Hz): δ 9.55 (d, J = 8.1 Hz, 1 H, CHO), 7.42 (d, J = 15.6 Hz, 1H, CH=CH), 6.34 (dd, J = 15.6, 8.1 Hz, 1 H, CH=CH), 4.55–4.51 (m, 4 H, H-Cp), 4.17 (br. s, 5 H, H-Cp). ¹³C NMR (150.9 MHz, CDCl₃): δ 193.3, 155.2, 126.5, 77.9, 72.0 (2C), 70.1 (5C), 69.3 (2C). IR (KBr, cm⁻¹): 1670 (C=O), 1618 (C=C).

Figure 5
Synthesis scheme for (I).

5. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The hydrogen atom positions were calculated geometrically at distances of 0.95 Å and refined using a riding model with U_iso(H) = 1.2U_eq(C).

Table 2
Experimental details

Crystal data
Chemical formula	[Fe(C₅H₅)(C₈H₇O)]
M_r	240.08
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	100
a, b, c (Å)	5.77599 (11), 7.38297 (13), 24.4180 (4)
V (Å³)	1041.28 (3)
Z	4
Radiation type	Cu Kα
μ (mm⁻¹)	11.33
Crystal size (mm)	0.13 × 0.12 × 0.06

Data collection
Diffractometer	XtaLAB Synergy, Single source at home/near, HyPix-Bantam
Absorption correction	Multi-scan (CrysAlis PRO; Rigaku OD, 2021 )
T_min, T_max	0.235, 0.500
No. of measured, independent and observed [I > 2σ(I)] reflections	6966, 2068, 1988
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.634

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.026, 0.068, 1.07
No. of reflections	2068
No. of parameters	137
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.34
Absolute structure	Flack x determined using 691 quotients [(I⁺)−(I⁻)]/[(I⁺)+(I⁻)] (Parsons et al., 2013 )
Absolute structure parameter	0.008 (3)
Computer programs: CrysAlis PRO (Rigaku OD, 2021), SHELXT (Sheldrick, 2015a ), SHELXL (Sheldrick, 2015b ) and SHELXTL (Sheldrick, 2008 ).

Supporting information

CCDC reference: 2579562

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S2056989026008170/hb8242sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989026008170/hb8242Isup2.hkl

checkCIF report

Computing details top

3-Ferrocenylprop-2-en-1-one top

Crystal data top

[Fe(C₅H₅)(C₈H₇O)]	D_x = 1.531 Mg m⁻³
M_r = 240.08	Cu Kα radiation, λ = 1.54184 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 4753 reflections
a = 5.77599 (11) Å	θ = 3.6–77.0°
b = 7.38297 (13) Å	µ = 11.33 mm⁻¹
c = 24.4180 (4) Å	T = 100 K
V = 1041.28 (3) Å³	Plate, red
Z = 4	0.13 × 0.12 × 0.06 mm
F(000) = 496

Data collection top

XtaLAB Synergy, Single source at home/near, HyPix-Bantam diffractometer	1988 reflections with I > 2σ(I)
Radiation source: micro-focus sealed X-ray tube	R_int = 0.029
ω scans	θ_max = 77.7°, θ_min = 3.6°
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2021)	h = −7→7
T_min = 0.235, T_max = 0.500	k = −9→9
6966 measured reflections	l = −30→18
2068 independent reflections

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.026	w = 1/[σ²(F_o²) + (0.0399P)² + 0.3106P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.068	(Δ/σ)_max < 0.001
S = 1.07	Δρ_max = 0.33 e Å⁻³
2068 reflections	Δρ_min = −0.34 e Å⁻³
137 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0018 (2)
Primary atom site location: dual	Absolute structure: Flack x determined using 691 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.008 (3)

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
Fe1	0.25332 (7)	0.37182 (5)	0.34479 (2)	0.01172 (14)
O1	0.2819 (4)	0.7387 (3)	0.57138 (9)	0.0316 (5)
C1	0.2447 (6)	0.2947 (3)	0.42514 (9)	0.0157 (5)
C2	0.3681 (5)	0.1630 (3)	0.39272 (10)	0.0163 (5)
H2	0.5245	0.1270	0.3978	0.020*
C3	0.2161 (5)	0.0969 (3)	0.35218 (10)	0.0176 (5)
H3	0.2533	0.0088	0.3252	0.021*
C4	−0.0028 (5)	0.1839 (4)	0.35833 (10)	0.0161 (5)
H4	−0.1366	0.1631	0.3366	0.019*
C5	0.0149 (5)	0.3083 (4)	0.40315 (10)	0.0156 (5)
H5	−0.1043	0.3860	0.4160	0.019*
C6	0.3912 (5)	0.6273 (4)	0.34172 (11)	0.0201 (6)
H6	0.4386	0.6984	0.3721	0.024*
C7	0.5323 (5)	0.5044 (4)	0.31226 (13)	0.0254 (7)
H7	0.6903	0.4782	0.3195	0.030*
C8	0.3956 (6)	0.4274 (4)	0.26994 (12)	0.0292 (8)
H8	0.4463	0.3408	0.2438	0.035*
C9	0.1703 (6)	0.5024 (4)	0.27361 (11)	0.0258 (7)
H9	0.0432	0.4750	0.2504	0.031*
C10	0.1680 (5)	0.6261 (4)	0.31821 (12)	0.0218 (6)
H10	0.0390	0.6957	0.3301	0.026*
C11	0.3472 (5)	0.4031 (4)	0.46809 (10)	0.0167 (5)
H11	0.5093	0.3902	0.4734	0.020*
C12	0.2373 (6)	0.5198 (3)	0.50116 (10)	0.0180 (5)
H12	0.0743	0.5344	0.4984	0.022*
C13	0.3669 (5)	0.6241 (4)	0.54122 (11)	0.0222 (6)
H13	0.5284	0.6018	0.5442	0.027*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe1	0.0133 (2)	0.0100 (2)	0.01192 (19)	0.0000 (2)	0.00116 (18)	0.00123 (12)
O1	0.0332 (14)	0.0303 (11)	0.0311 (10)	−0.0015 (11)	0.0040 (10)	−0.0137 (9)
C1	0.0179 (12)	0.0148 (10)	0.0143 (10)	−0.0004 (14)	0.0018 (12)	0.0045 (9)
C2	0.0177 (12)	0.0120 (11)	0.0190 (11)	0.0029 (11)	0.0022 (10)	0.0069 (10)
C3	0.0240 (14)	0.0082 (10)	0.0205 (11)	−0.0009 (11)	0.0022 (11)	0.0019 (9)
C4	0.0166 (12)	0.0129 (11)	0.0189 (11)	−0.0031 (11)	0.0022 (10)	0.0005 (10)
C5	0.0152 (12)	0.0171 (13)	0.0146 (11)	−0.0012 (11)	0.0023 (10)	0.0025 (10)
C6	0.0279 (15)	0.0138 (12)	0.0186 (12)	−0.0049 (12)	−0.0016 (11)	0.0053 (12)
C7	0.0156 (14)	0.0220 (14)	0.0385 (16)	−0.0009 (11)	0.0060 (12)	0.0150 (13)
C8	0.050 (2)	0.0190 (15)	0.0189 (13)	−0.0055 (15)	0.0220 (14)	−0.0003 (12)
C9	0.0365 (18)	0.0252 (15)	0.0158 (13)	−0.0102 (13)	−0.0082 (11)	0.0107 (11)
C10	0.0251 (14)	0.0132 (12)	0.0272 (13)	0.0021 (12)	0.0052 (11)	0.0105 (12)
C11	0.0172 (12)	0.0190 (13)	0.0138 (11)	−0.0024 (11)	−0.0004 (10)	0.0057 (10)
C12	0.0186 (13)	0.0190 (11)	0.0164 (11)	−0.0013 (13)	0.0017 (12)	0.0027 (9)
C13	0.0248 (14)	0.0218 (14)	0.0199 (12)	−0.0032 (13)	0.0005 (11)	0.0003 (11)

Geometric parameters (Å, º) top

Fe1—C5	2.036 (3)	C4—C5	1.432 (4)
Fe1—C1	2.043 (2)	C4—H4	0.9500
Fe1—C9	2.045 (3)	C5—H5	0.9500
Fe1—C8	2.046 (3)	C6—C10	1.411 (4)
Fe1—C7	2.046 (3)	C6—C7	1.416 (4)
Fe1—C2	2.046 (3)	C6—H6	0.9500
Fe1—C10	2.047 (3)	C7—C8	1.419 (5)
Fe1—C6	2.049 (3)	C7—H7	0.9500
Fe1—C3	2.049 (2)	C8—C9	1.418 (5)
Fe1—C4	2.055 (3)	C8—H8	0.9500
O1—C13	1.224 (4)	C9—C10	1.421 (4)
C1—C5	1.435 (4)	C9—H9	0.9500
C1—C2	1.442 (4)	C10—H10	0.9500
C1—C11	1.446 (4)	C11—C12	1.341 (4)
C2—C3	1.411 (4)	C11—H11	0.9500
C2—H2	0.9500	C12—C13	1.452 (4)
C3—C4	1.426 (4)	C12—H12	0.9500
C3—H3	0.9500	C13—H13	0.9500

C5—Fe1—C1	41.19 (11)	C2—C3—C4	108.8 (2)
C5—Fe1—C9	123.02 (12)	C2—C3—Fe1	69.72 (15)
C1—Fe1—C9	160.35 (13)	C4—C3—Fe1	69.88 (15)
C5—Fe1—C8	160.59 (13)	C2—C3—H3	125.6
C1—Fe1—C8	157.44 (15)	C4—C3—H3	125.6
C9—Fe1—C8	40.56 (14)	Fe1—C3—H3	126.4
C5—Fe1—C7	156.14 (13)	C3—C4—C5	107.8 (2)
C1—Fe1—C7	121.69 (13)	C3—C4—Fe1	69.46 (15)
C9—Fe1—C7	68.22 (13)	C5—C4—Fe1	68.81 (16)
C8—Fe1—C7	40.60 (14)	C3—C4—H4	126.1
C5—Fe1—C2	69.22 (11)	C5—C4—H4	126.1
C1—Fe1—C2	41.31 (10)	Fe1—C4—H4	127.2
C9—Fe1—C2	156.58 (12)	C4—C5—C1	107.9 (2)
C8—Fe1—C2	122.14 (13)	C4—C5—Fe1	70.21 (15)
C7—Fe1—C2	109.12 (12)	C1—C5—Fe1	69.67 (14)
C5—Fe1—C10	105.69 (11)	C4—C5—H5	126.0
C1—Fe1—C10	123.64 (11)	C1—C5—H5	126.0
C9—Fe1—C10	40.65 (12)	Fe1—C5—H5	125.7
C8—Fe1—C10	68.26 (12)	C10—C6—C7	108.4 (3)
C7—Fe1—C10	68.14 (12)	C10—C6—Fe1	69.77 (17)
C2—Fe1—C10	161.92 (12)	C7—C6—Fe1	69.66 (17)
C5—Fe1—C6	120.03 (12)	C10—C6—H6	125.8
C1—Fe1—C6	107.52 (11)	C7—C6—H6	125.8
C9—Fe1—C6	68.03 (11)	Fe1—C6—H6	126.3
C8—Fe1—C6	68.08 (12)	C6—C7—C8	107.9 (3)
C7—Fe1—C6	40.47 (12)	C6—C7—Fe1	69.87 (17)
C2—Fe1—C6	126.07 (11)	C8—C7—Fe1	69.70 (17)
C10—Fe1—C6	40.31 (12)	C6—C7—H7	126.1
C5—Fe1—C3	68.85 (11)	C8—C7—H7	126.1
C1—Fe1—C3	68.72 (10)	Fe1—C7—H7	125.9
C9—Fe1—C3	121.15 (11)	C9—C8—C7	107.9 (2)
C8—Fe1—C3	108.62 (12)	C9—C8—Fe1	69.69 (16)
C7—Fe1—C3	126.21 (12)	C7—C8—Fe1	69.71 (16)
C2—Fe1—C3	40.29 (11)	C9—C8—H8	126.0
C10—Fe1—C3	155.68 (12)	C7—C8—H8	126.0
C6—Fe1—C3	162.95 (12)	Fe1—C8—H8	126.1
C5—Fe1—C4	40.98 (11)	C8—C9—C10	108.0 (3)
C1—Fe1—C4	68.90 (11)	C8—C9—Fe1	69.75 (16)
C9—Fe1—C4	106.63 (12)	C10—C9—Fe1	69.74 (16)
C8—Fe1—C4	124.63 (12)	C8—C9—H9	126.0
C7—Fe1—C4	162.27 (12)	C10—C9—H9	126.0
C2—Fe1—C4	68.44 (11)	Fe1—C9—H9	126.1
C10—Fe1—C4	119.80 (12)	C6—C10—C9	107.9 (3)
C6—Fe1—C4	155.13 (12)	C6—C10—Fe1	69.92 (17)
C3—Fe1—C4	40.67 (11)	C9—C10—Fe1	69.60 (16)
C5—C1—C2	107.4 (2)	C6—C10—H10	126.1
C5—C1—C11	127.7 (2)	C9—C10—H10	126.1
C2—C1—C11	124.7 (3)	Fe1—C10—H10	126.0
C5—C1—Fe1	69.14 (13)	C12—C11—C1	126.8 (3)
C2—C1—Fe1	69.44 (13)	C12—C11—H11	116.6
C11—C1—Fe1	122.16 (18)	C1—C11—H11	116.6
C3—C2—C1	108.1 (2)	C11—C12—C13	120.2 (3)
C3—C2—Fe1	69.98 (14)	C11—C12—H12	119.9
C1—C2—Fe1	69.25 (13)	C13—C12—H12	119.9
C3—C2—H2	125.9	O1—C13—C12	124.4 (3)
C1—C2—H2	125.9	O1—C13—H13	117.8
Fe1—C2—H2	126.4	C12—C13—H13	117.8

C5—C1—C2—C3	−0.4 (3)	Fe1—C6—C7—C8	59.6 (2)
C11—C1—C2—C3	−175.0 (2)	C10—C6—C7—Fe1	−59.22 (19)
Fe1—C1—C2—C3	−59.39 (18)	C6—C7—C8—C9	−0.3 (3)
C5—C1—C2—Fe1	58.95 (16)	Fe1—C7—C8—C9	59.43 (19)
C11—C1—C2—Fe1	−115.6 (2)	C6—C7—C8—Fe1	−59.7 (2)
C1—C2—C3—C4	−0.2 (3)	C7—C8—C9—C10	0.1 (3)
Fe1—C2—C3—C4	−59.14 (18)	Fe1—C8—C9—C10	59.51 (18)
C1—C2—C3—Fe1	58.94 (17)	C7—C8—C9—Fe1	−59.44 (19)
C2—C3—C4—C5	0.8 (3)	C7—C6—C10—C9	−0.3 (3)
Fe1—C3—C4—C5	−58.28 (18)	Fe1—C6—C10—C9	−59.47 (19)
C2—C3—C4—Fe1	59.04 (18)	C7—C6—C10—Fe1	59.15 (19)
C3—C4—C5—C1	−1.0 (3)	C8—C9—C10—C6	0.2 (3)
Fe1—C4—C5—C1	−59.71 (17)	Fe1—C9—C10—C6	59.67 (19)
C3—C4—C5—Fe1	58.68 (18)	C8—C9—C10—Fe1	−59.51 (19)
C2—C1—C5—C4	0.9 (3)	C5—C1—C11—C12	10.4 (4)
C11—C1—C5—C4	175.2 (2)	C2—C1—C11—C12	−176.2 (2)
Fe1—C1—C5—C4	60.05 (17)	Fe1—C1—C11—C12	97.8 (3)
C2—C1—C5—Fe1	−59.14 (16)	C1—C11—C12—C13	−177.7 (2)
C11—C1—C5—Fe1	115.2 (3)	C11—C12—C13—O1	176.8 (3)
C10—C6—C7—C8	0.4 (3)

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C6–C10 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1ⁱ	0.95	2.46	3.252 (3)	141
C8—H8···Cg2ⁱⁱ	0.95	2.82	3.736 (3)	161

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

Acknowledgements

The author's contributions are as follows. Conceptualization, TH and ANB; synthesis, ERS and VPZ; NMR analysis, ERS; X-ray analysis, VNK; Hirshfeld surface analysis, TH; writing (review and editing of the manuscript) TH, KIH and NAG; supervision, TH and ANB.

Funding information

This work has been supported by the RUDN University Scientific Projects Grant System, Project No: 021422–2-000, as well as by the Azerbaijan Medical University and Baku Engineering University. TH is also grateful to Hacettepe University Scientific Research Project Unit (grant No. 013 D04 602 004).

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