N-Ferrocenymethyl-N-phenyl­acetamide

Khelef, A.; Mahboub, M.S.; Lanez, T.

doi:10.1107/S2414314616002030

metal-organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 1| Part 2| February 2016| x160203

https://doi.org/10.1107/S2414314616002030

Open

access

N-Ferrocenymethyl-N-phenylacetamide

Abdelhamid Khelef,^a Mohammed Sadok Mahboub ^b and Touhami Lanez ^a ^*

^aVTRS Laboratory, Department of Chemistry, Faculty of Exact Sciences, University of El-Oued, PO Box 789, El-Oued 39000, Algeria, and ^bLEVRES Laboratory, Department of Physics, Faculty of Exact Sciences, University of El-Oued, PO Box 789, El-Oued 39000, Algeria
^*Correspondence e-mail: lanezt@gmail.com

Edited by J. Simpson, University of Otago, New Zealand (Received 18 January 2016; accepted 2 February 2016; online 10 February 2016)

In the title compound, [Fe(C₅H₅)(C₁₄H₁₄NO)], the asymmetric unit comprises two unique molecules. The two cyclopentadienyl (Cp) rings of each ferrocene residue are nearly parallel to one another. In each substituted Cp ring, the CH₂ group carries an N-phenylacetamide residue. In the crystal, C—H⋯O hydrogen bonds stack molecules along a.

Keywords: crystal structure; N-ferrocenymethyl-N-phenylacetamide; hydrogen bonding.

CCDC reference: 1451430

Structure description

Ferrocene and its derivatives are known to be of considerable interest, because of their use in organic synthesis (Khand et al., 1989 ), catalysis (Szarka et al., 2004 ), materials science (Uno & Dixneuf, 1998 ), asymmetric synthesis (Torres et al., 2002 ), medicinal chemistry (Chavain et al., 2009 ) and electrochemistry (Ahmedi & Lanez, 2011 ; Khelef & Lanez, 2015 ). As a continuation of our research related to ferrocene derivatives (Khelef et al., 2012 ; Rahim et al., 2012 ), we report the synthesis and structural characterization of the title compound.

The asymmetric unit of title compound comprises two crystallographically independent molecules, A and B (Fig. 1). The two cyclopentadienyl (Cp) rings of each ferrocene residue are nearly parallel to one another, the dihedral angle between the mean planes of Cp1/Cp2 is 3.2 (2)° and Cp3/Cp4 is 2.6 (2)° (Cp1 = C1A–C5A, Cp2 = C6A–C10A, Cp2 = C1B–C5B and Cp4 = C6B–C10B). The Cp rings are essentially parallel and the Fe⋯centroid distances are 1.648 (3) (Cp1), 1.640 (3) (Cp2), 1.652 (3) (Cp3) and 1.645 (3) Å (Cp4). The [Cg1⋯Fe1⋯Cg2] angle is 178.16 (2)° and [Cg3⋯Fe2⋯Cg4] angle is 179.21 (2)° [Cg1, Cg2, Cg3 and Cg4 are the centroids of the Cp1, Cp2, Cp3 and Cp4 rings, respectively].

Figure 1
The molecular structure of the title compound, showing the atomic numbering scheme and 50% probability displacement ellipsoids.

In each molecule one of the Cp rings is substituted by an amide group which is essentially perpendicular to the substituted cyclopentadienyl ring [torsion angles C14A—N1—C11A—C10A and C14B—N2—C11B—C10B are 93.3 (4) and −93.3 (4)°, respectively]. In the methanoyl group, the N and O atoms are coplanar [the C11A—N1—C12A—O1 torsion angle is −0.6 (5)° and the C11B—N2—C12B—O2 torsion angle is −2.9 (6)°]. In the crystal, C—H⋯O hydrogen bonds, Table 1, combine to stack the molecules along the a axis, Fig. 2.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15A—H15A⋯O1ⁱ	0.93	2.56	3.456 (5)	162
C19B—H19B⋯O2ⁱⁱ	0.93	2.55	3.421 (5)	157
C15A—H15A⋯O1ⁱ	0.93	2.56	3.456 (5)	162
C19B—H19B⋯O2ⁱⁱ	0.93	2.55	3.421 (5)	157
Symmetry codes: (i) -x-1, -y+2, -z+1; (ii) -x, -y+1, -z+2.

Figure 2
The crystal packing of the title compound, viewed along the b axis, with hydrogen bonds drawn as dashed lines.

Synthesis and crystallization

N-ferrocenylmethylaniline was obtained as described in the literature (Osgerby & Pauson, 1961 ). To a 250 ml round-bottom flask equipped with a reflux condenser and a magnetic stirrer a suspension of N-ferrocenylmethylaniline (6 g, 20 mmol) in 50 ml of dry toluene was added under a nitrogen atmosphere. The resulting suspension was heated at 50°C until all the solid materials had dissolved completely. 50 ml of anhydride acetic acid was then added and the resulting mixture was vigorously stirred under reflux for 20 min. The reaction mixture was then poured into water; the organic layer was separated, washed twice with water, dried over MgSO₄ and evaporated. The residue was recrystallized from a mixture of ethanol–water to yield N-ferrocenymethyl-N-phenylacetamide as orange needles (yield: 5.6 g, 81.5%; m.p. 116–117°C). The compounds gave clean ¹H and ¹³C NMR spectra in CDCl₃. NMR ¹H (300 MHz, CDCl₃) 1.75 (s, 3H, CH₃), 4.03 (s, 4H, C₅H₄), 4.08 (s, 5H, C₅H₅), 4.61 (s, 2H, CH₂), 6.99 (d, 2H, ortho-C₆H₅), 7.28–7.35 (m, 3H, meta- and para-C₆H₅). NMR ¹³C (75 MHz, CDCl₃) 22.83 (1C, CH₃), 48.40 (1C, CH₂), 68.13, 69.89 and 83.13 (5C, C5H4), 68.55 (5C, C₅H₅), 127.87, 128.55, 129.43, 142.84 (6C, C₆H₅), 169.74 (1C, CO).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	[Fe(C₅H₅)(C₁₄H₁₄NO)]
M_r	333.2
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	298
a, b, c (Å)	7.344 (1), 14.831 (1), 15.267 (1)
α, β, γ (°)	79.094 (10), 79.627 (10), 87.508 (10)
V (Å³)	1606.1 (3)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.94
Crystal size (mm)	0.3 × 0.1 × 0.1

Data collection
Diffractometer	Nonius KappaCCD
No. of measured, independent and observed [I > 2σ(I)] reflections	8635, 5157, 3765
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.588

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.115, 1.02
No. of reflections	5157
No. of parameters	398
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.28
Computer programs: COLLECT (Nonius, 1998 ), SIR92 (Altomare et al., 1993 ), SHELXL2014 (Sheldrick, 2015 ), ORTEP-3 for Windows (Farrugia, 2012 ), Mercury (Macrae et al., 2008 ), WinGX (Farrugia, 2012).

Structural data

CCDC reference: 1451430

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2414314616002030/sj5494sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314616002030/sj5494Isup2.hkl

a new CIF. DOI: https://doi.org/10.1107/S2414314616002030/sj5494sup3.txt

checkCIF report

Computing details top

Data collection: COLLECT (Nonius, 1998); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: WinGX (Farrugia, 2012).

N-Ferrocenymethyl-N-phenylacetamide top

Crystal data top

[Fe(C₅H₅)(C₁₄H₁₄NO)]	Z = 4
M_r = 333.2	F(000) = 696
Triclinic, P1	D_x = 1.378 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.344 (1) Å	Cell parameters from 5157 reflections
b = 14.831 (1) Å	θ = 2.8–24.7°
c = 15.267 (1) Å	µ = 0.94 mm⁻¹
α = 79.094 (10)°	T = 298 K
β = 79.627 (10)°	Needle, orange
γ = 87.508 (10)°	0.3 × 0.1 × 0.1 mm
V = 1606.1 (3) Å³

Data collection top

Nonius KappaCCD diffractometer	R_int = 0.039
Radiation source: fine-focus sealed tube	θ_max = 24.7°, θ_min = 2.8°
CCD scans	h = −8→8
8635 measured reflections	k = −17→17
5157 independent reflections	l = −15→17
3765 reflections with I > 2σ(I)

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.042	w = 1/[σ²(F_o²) + (0.0489P)² + 0.6059P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.115	(Δ/σ)_max = 0.001
S = 1.02	Δρ_max = 0.37 e Å⁻³
5157 reflections	Δρ_min = −0.28 e Å⁻³
398 parameters	Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0049 (12)
0 constraints

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
Fe2	0.46219 (6)	0.43859 (3)	0.69245 (3)	0.04595 (17)
Fe1	0.06009 (6)	0.92687 (3)	0.17945 (3)	0.04206 (17)
O1	−0.5391 (4)	0.9627 (2)	0.3939 (2)	0.0854 (10)
C14A	−0.2433 (5)	0.8074 (2)	0.5143 (2)	0.0462 (8)
N2	0.1143 (4)	0.6002 (2)	0.8775 (2)	0.0570 (8)
C10B	0.2785 (5)	0.5231 (2)	0.7548 (2)	0.0473 (8)
N1	−0.3111 (4)	0.8744 (2)	0.44649 (18)	0.0524 (7)
O2	−0.1384 (5)	0.5145 (2)	0.8928 (2)	0.0918 (10)
C3A	0.2181 (5)	0.9949 (3)	0.0637 (3)	0.0555 (9)
H3A	0.2196	0.9852	0.0051	0.067*
C10A	−0.1303 (4)	0.8808 (2)	0.2910 (2)	0.0445 (8)
C7A	−0.1331 (5)	0.8472 (3)	0.1509 (3)	0.0578 (10)
H7A	−0.1637	0.8476	0.0943	0.069*
C1B	0.7309 (6)	0.4029 (3)	0.6688 (5)	0.0860 (16)
H1B	0.8239	0.4413	0.6337	0.103*
C14B	0.2045 (5)	0.6821 (2)	0.8845 (2)	0.0510 (9)
C11A	−0.1712 (6)	0.9246 (3)	0.3737 (2)	0.0610 (10)
H11A	−0.0575	0.9277	0.3969	0.073*
H11B	−0.215	0.987	0.3565	0.073*
C5A	0.2862 (6)	0.9844 (3)	0.2041 (3)	0.0702 (12)
H5A	0.3401	0.9666	0.2554	0.084*
C9B	0.1873 (5)	0.4692 (3)	0.7081 (3)	0.0560 (10)
H10B	0.0918	0.4282	0.7341	0.067*
C6B	0.4137 (5)	0.5750 (2)	0.6887 (3)	0.0600 (10)
H8B	0.4938	0.6167	0.7	0.072*
C8B	0.2676 (6)	0.4892 (3)	0.6154 (3)	0.0670 (12)
H6B	0.2336	0.4638	0.5695	0.08*
C15B	0.2566 (6)	0.7485 (3)	0.8087 (3)	0.0630 (10)
H15B	0.2272	0.7424	0.7534	0.076*
C19A	−0.1770 (6)	0.7239 (3)	0.4957 (3)	0.0623 (10)
H19A	−0.1825	0.7092	0.4397	0.075*
C16A	−0.1674 (7)	0.7642 (3)	0.6620 (3)	0.0860 (15)
H16A	−0.1669	0.7775	0.7191	0.103*
C15A	−0.2392 (6)	0.8279 (3)	0.5980 (3)	0.0701 (12)
H15A	−0.2843	0.8842	0.6116	0.084*
C11B	0.2372 (6)	0.5234 (3)	0.8542 (3)	0.0638 (10)
H11C	0.1794	0.4658	0.8854	0.077*
H11D	0.3526	0.5274	0.8757	0.077*
C19B	0.2455 (5)	0.6916 (3)	0.9662 (3)	0.0593 (10)
H19B	0.2109	0.6467	1.0174	0.071*
C16B	0.3528 (6)	0.8243 (3)	0.8152 (3)	0.0693 (12)
H16B	0.3899	0.8686	0.7639	0.083*
C7B	0.4077 (6)	0.5539 (3)	0.6044 (3)	0.0683 (12)
H7B	0.4833	0.5783	0.5502	0.082*
C17B	0.3936 (5)	0.8344 (3)	0.8966 (3)	0.0687 (11)
H17B	0.458	0.8855	0.901	0.082*
C13B	−0.1921 (6)	0.6659 (3)	0.9251 (3)	0.0840 (14)
H13D	−0.1149	0.7167	0.9247	0.126*
H13E	−0.2758	0.6843	0.8833	0.126*
H13F	−0.2614	0.6468	0.985	0.126*
C18B	0.3386 (6)	0.7683 (3)	0.9719 (3)	0.0715 (12)
H18B	0.3646	0.7755	1.0276	0.086*
C18A	−0.1024 (6)	0.6619 (3)	0.5591 (3)	0.0678 (11)
H18A	−0.0554	0.606	0.5452	0.081*
C12B	−0.0721 (6)	0.5868 (3)	0.8974 (3)	0.0661 (11)
C13A	−0.6325 (5)	0.8459 (3)	0.5234 (3)	0.0755 (12)
H13A	−0.5703	0.7993	0.5603	0.113*
H13B	−0.6982	0.8867	0.5602	0.113*
H13C	−0.7184	0.8176	0.4966	0.113*
C5B	0.6691 (9)	0.3963 (4)	0.7606 (5)	0.108 (2)
H5B	0.7128	0.4286	0.7991	0.13*
C12A	−0.4920 (6)	0.8994 (3)	0.4496 (3)	0.0603 (10)
C3B	0.5097 (7)	0.3011 (3)	0.7083 (5)	0.0904 (17)
H3B	0.4254	0.2576	0.7046	0.108*
C17A	−0.0971 (6)	0.6820 (3)	0.6423 (3)	0.0712 (12)
H17A	−0.0463	0.6403	0.6851	0.085*
C2B	0.6325 (7)	0.3434 (4)	0.6386 (4)	0.0820 (14)
H2B	0.6478	0.3336	0.5793	0.098*
C4B	0.5260 (8)	0.3308 (5)	0.7846 (4)	0.104 (2)
H4B	0.4566	0.3118	0.842	0.125*
C6A	−0.2156 (4)	0.9027 (2)	0.2139 (2)	0.0473 (8)
H6A	−0.3095	0.946	0.2058	0.057*
C9A	0.0048 (5)	0.8118 (2)	0.2743 (3)	0.0565 (10)
H9A	0.0823	0.7844	0.3139	0.068*
C2A	0.1019 (5)	1.0569 (3)	0.1067 (3)	0.0598 (10)
H2A	0.0129	1.0951	0.0821	0.072*
C8A	0.0022 (6)	0.7917 (3)	0.1888 (3)	0.0643 (11)
H8A	0.0774	0.7489	0.1617	0.077*
C4A	0.3312 (5)	0.9501 (3)	0.1231 (3)	0.0606 (10)
H4A	0.4205	0.9056	0.1111	0.073*
C1A	0.1441 (6)	1.0510 (3)	0.1936 (3)	0.0699 (12)
H1A	0.0884	1.0849	0.2368	0.084*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe2	0.0372 (3)	0.0402 (3)	0.0616 (3)	0.0043 (2)	−0.0144 (2)	−0.0080 (2)
Fe1	0.0369 (3)	0.0396 (3)	0.0473 (3)	−0.00241 (19)	−0.0069 (2)	−0.0021 (2)
O1	0.109 (2)	0.079 (2)	0.0712 (19)	0.0397 (18)	−0.0356 (17)	−0.0112 (17)
C14A	0.0495 (19)	0.043 (2)	0.0428 (19)	0.0045 (15)	−0.0064 (14)	−0.0025 (16)
N2	0.071 (2)	0.0462 (18)	0.0552 (19)	0.0011 (15)	−0.0074 (15)	−0.0164 (15)
C10B	0.047 (2)	0.041 (2)	0.058 (2)	0.0054 (15)	−0.0164 (16)	−0.0133 (17)
N1	0.0625 (19)	0.0486 (18)	0.0406 (16)	0.0073 (14)	−0.0026 (13)	−0.0021 (14)
O2	0.107 (3)	0.076 (2)	0.091 (2)	−0.0400 (19)	−0.0019 (18)	−0.0184 (18)
C3A	0.053 (2)	0.058 (2)	0.055 (2)	−0.0172 (18)	−0.0041 (17)	−0.0073 (19)
C10A	0.0441 (19)	0.0402 (19)	0.0457 (19)	−0.0021 (14)	−0.0062 (14)	−0.0005 (15)
C7A	0.063 (2)	0.058 (2)	0.049 (2)	−0.0259 (19)	−0.0017 (17)	−0.0067 (19)
C1B	0.049 (3)	0.053 (3)	0.140 (5)	0.005 (2)	−0.009 (3)	0.014 (3)
C14B	0.056 (2)	0.045 (2)	0.051 (2)	0.0004 (16)	−0.0041 (16)	−0.0131 (17)
C11A	0.077 (3)	0.051 (2)	0.051 (2)	−0.0078 (19)	−0.0100 (19)	−0.0004 (18)
C5A	0.059 (3)	0.090 (3)	0.065 (3)	−0.030 (2)	−0.021 (2)	−0.005 (2)
C9B	0.0389 (19)	0.056 (2)	0.078 (3)	0.0079 (16)	−0.0175 (18)	−0.021 (2)
C6B	0.053 (2)	0.040 (2)	0.084 (3)	0.0015 (16)	−0.0076 (19)	−0.009 (2)
C8B	0.069 (3)	0.079 (3)	0.064 (3)	0.036 (2)	−0.031 (2)	−0.032 (2)
C15B	0.081 (3)	0.052 (2)	0.052 (2)	0.002 (2)	−0.0035 (19)	−0.0068 (19)
C19A	0.087 (3)	0.048 (2)	0.050 (2)	0.006 (2)	−0.0067 (19)	−0.0074 (18)
C16A	0.139 (4)	0.065 (3)	0.070 (3)	0.020 (3)	−0.061 (3)	−0.017 (2)
C15A	0.101 (3)	0.050 (2)	0.066 (3)	0.019 (2)	−0.031 (2)	−0.019 (2)
C11B	0.086 (3)	0.047 (2)	0.062 (2)	0.008 (2)	−0.022 (2)	−0.0129 (19)
C19B	0.071 (3)	0.055 (2)	0.051 (2)	−0.0111 (19)	−0.0023 (18)	−0.0106 (19)
C16B	0.081 (3)	0.048 (2)	0.068 (3)	−0.001 (2)	0.010 (2)	−0.004 (2)
C7B	0.071 (3)	0.061 (3)	0.062 (3)	0.026 (2)	−0.001 (2)	−0.002 (2)
C17B	0.061 (3)	0.056 (3)	0.087 (3)	−0.0099 (19)	0.006 (2)	−0.023 (2)
C13B	0.070 (3)	0.075 (3)	0.095 (4)	−0.001 (2)	0.009 (2)	−0.009 (3)
C18B	0.081 (3)	0.074 (3)	0.061 (3)	−0.012 (2)	−0.006 (2)	−0.020 (2)
C18A	0.084 (3)	0.045 (2)	0.068 (3)	0.013 (2)	−0.008 (2)	−0.004 (2)
C12B	0.078 (3)	0.062 (3)	0.054 (2)	−0.012 (2)	0.0000 (19)	−0.007 (2)
C13A	0.057 (3)	0.089 (3)	0.079 (3)	0.010 (2)	−0.006 (2)	−0.021 (3)
C5B	0.113 (5)	0.096 (4)	0.160 (6)	0.060 (4)	−0.102 (5)	−0.075 (4)
C12A	0.078 (3)	0.056 (2)	0.051 (2)	0.019 (2)	−0.0197 (19)	−0.019 (2)
C3B	0.065 (3)	0.046 (3)	0.155 (6)	0.001 (2)	−0.034 (3)	0.008 (3)
C17A	0.087 (3)	0.054 (3)	0.076 (3)	0.006 (2)	−0.038 (2)	0.000 (2)
C2B	0.088 (4)	0.076 (3)	0.090 (4)	0.046 (3)	−0.035 (3)	−0.030 (3)
C4B	0.092 (4)	0.126 (5)	0.067 (3)	0.054 (4)	−0.003 (3)	0.024 (3)
C6A	0.0379 (18)	0.048 (2)	0.051 (2)	−0.0018 (15)	−0.0074 (14)	0.0028 (17)
C9A	0.053 (2)	0.047 (2)	0.061 (2)	0.0054 (16)	−0.0079 (17)	0.0093 (18)
C2A	0.058 (2)	0.045 (2)	0.070 (3)	−0.0051 (17)	−0.0093 (19)	0.0036 (19)
C8A	0.070 (3)	0.043 (2)	0.071 (3)	−0.0047 (18)	0.013 (2)	−0.011 (2)
C4A	0.038 (2)	0.059 (2)	0.080 (3)	−0.0057 (16)	−0.0078 (18)	−0.003 (2)
C1A	0.071 (3)	0.061 (3)	0.075 (3)	−0.027 (2)	0.011 (2)	−0.021 (2)

Geometric parameters (Å, º) top

Fe2—C5B	2.006 (4)	C5A—H5A	0.93
Fe2—C1B	2.008 (4)	C9B—C8B	1.413 (5)
Fe2—C4B	2.019 (5)	C9B—H10B	0.93
Fe2—C3B	2.030 (4)	C6B—C7B	1.389 (6)
Fe2—C6B	2.031 (4)	C6B—H8B	0.93
Fe2—C9B	2.031 (3)	C8B—C7B	1.403 (6)
Fe2—C10B	2.034 (3)	C8B—H6B	0.93
Fe2—C2B	2.037 (4)	C15B—C16B	1.381 (6)
Fe2—C7B	2.038 (4)	C15B—H15B	0.93
Fe2—C8B	2.041 (4)	C19A—C18A	1.376 (5)
Fe1—C9A	2.022 (3)	C19A—H19A	0.93
Fe1—C5A	2.024 (4)	C16A—C17A	1.368 (6)
Fe1—C10A	2.026 (3)	C16A—C15A	1.385 (5)
Fe1—C1A	2.028 (4)	C16A—H16A	0.93
Fe1—C6A	2.028 (3)	C15A—H15A	0.93
Fe1—C4A	2.038 (3)	C11B—H11C	0.97
Fe1—C8A	2.040 (4)	C11B—H11D	0.97
Fe1—C2A	2.040 (4)	C19B—C18B	1.377 (5)
Fe1—C7A	2.041 (4)	C19B—H19B	0.93
Fe1—C3A	2.044 (4)	C16B—C17B	1.366 (6)
O1—C12A	1.224 (4)	C16B—H16B	0.93
C14A—C19A	1.372 (5)	C7B—H7B	0.93
C14A—C15A	1.374 (5)	C17B—C18B	1.373 (6)
C14A—N1	1.435 (4)	C17B—H17B	0.93
N2—C12B	1.363 (5)	C13B—C12B	1.515 (6)
N2—C14B	1.439 (4)	C13B—H13D	0.96
N2—C11B	1.478 (4)	C13B—H13E	0.96
C10B—C6B	1.417 (5)	C13B—H13F	0.96
C10B—C9B	1.423 (5)	C18B—H18B	0.93
C10B—C11B	1.495 (5)	C18A—C17A	1.366 (6)
N1—C12A	1.359 (5)	C18A—H18A	0.93
N1—C11A	1.478 (4)	C13A—C12A	1.510 (5)
O2—C12B	1.216 (5)	C13A—H13A	0.96
C3A—C4A	1.396 (5)	C13A—H13B	0.96
C3A—C2A	1.402 (5)	C13A—H13C	0.96
C3A—H3A	0.93	C5B—C4B	1.413 (8)
C10A—C6A	1.409 (5)	C5B—H5B	0.93
C10A—C9A	1.420 (5)	C3B—C2B	1.337 (7)
C10A—C11A	1.506 (5)	C3B—C4B	1.347 (8)
C7A—C8A	1.398 (5)	C3B—H3B	0.93
C7A—C6A	1.421 (5)	C17A—H17A	0.93
C7A—H7A	0.93	C2B—H2B	0.93
C1B—C2B	1.357 (7)	C4B—H4B	0.93
C1B—C5B	1.379 (8)	C6A—H6A	0.93
C1B—H1B	0.93	C9A—C8A	1.397 (5)
C14B—C19B	1.369 (5)	C9A—H9A	0.93
C14B—C15B	1.377 (5)	C2A—C1A	1.401 (6)
C11A—H11A	0.97	C2A—H2A	0.93
C11A—H11B	0.97	C8A—H8A	0.93
C5A—C4A	1.406 (6)	C4A—H4A	0.93
C5A—C1A	1.414 (6)	C1A—H1A	0.93

C5B—Fe2—C1B	40.2 (2)	C4A—C5A—H5A	126.2
C5B—Fe2—C4B	41.1 (2)	C1A—C5A—H5A	126.2
C1B—Fe2—C4B	67.4 (2)	Fe1—C5A—H5A	125.4
C5B—Fe2—C3B	66.6 (2)	C8B—C9B—C10B	107.8 (4)
C1B—Fe2—C3B	65.69 (19)	C8B—C9B—Fe2	70.1 (2)
C4B—Fe2—C3B	38.9 (2)	C10B—C9B—Fe2	69.58 (19)
C5B—Fe2—C6B	110.1 (2)	C8B—C9B—H10B	126.1
C1B—Fe2—C6B	114.67 (18)	C10B—C9B—H10B	126.1
C4B—Fe2—C6B	136.1 (3)	Fe2—C9B—H10B	125.8
C3B—Fe2—C6B	174.9 (2)	C7B—C6B—C10B	109.2 (4)
C5B—Fe2—C9B	143.4 (3)	C7B—C6B—Fe2	70.3 (2)
C1B—Fe2—C9B	175.3 (2)	C10B—C6B—Fe2	69.7 (2)
C4B—Fe2—C9B	113.4 (2)	C7B—C6B—H8B	125.4
C3B—Fe2—C9B	111.81 (18)	C10B—C6B—H8B	125.4
C6B—Fe2—C9B	68.21 (15)	Fe2—C6B—H8B	126.2
C5B—Fe2—C10B	112.9 (2)	C7B—C8B—C9B	108.2 (4)
C1B—Fe2—C10B	143.6 (2)	C7B—C8B—Fe2	69.8 (2)
C4B—Fe2—C10B	109.84 (19)	C9B—C8B—Fe2	69.3 (2)
C3B—Fe2—C10B	135.9 (2)	C7B—C8B—H6B	125.9
C6B—Fe2—C10B	40.81 (14)	C9B—C8B—H6B	125.9
C9B—Fe2—C10B	41.00 (13)	Fe2—C8B—H6B	126.6
C5B—Fe2—C2B	66.5 (2)	C14B—C15B—C16B	119.8 (4)
C1B—Fe2—C2B	39.2 (2)	C14B—C15B—H15B	120.1
C4B—Fe2—C2B	65.7 (2)	C16B—C15B—H15B	120.1
C3B—Fe2—C2B	38.4 (2)	C14A—C19A—C18A	120.7 (4)
C6B—Fe2—C2B	144.9 (2)	C14A—C19A—H19A	119.7
C9B—Fe2—C2B	136.39 (19)	C18A—C19A—H19A	119.7
C10B—Fe2—C2B	174.3 (2)	C17A—C16A—C15A	120.9 (4)
C5B—Fe2—C7B	135.2 (3)	C17A—C16A—H16A	119.6
C1B—Fe2—C7B	111.34 (18)	C15A—C16A—H16A	119.6
C4B—Fe2—C7B	175.5 (3)	C14A—C15A—C16A	119.5 (4)
C3B—Fe2—C7B	145.2 (2)	C14A—C15A—H15A	120.2
C6B—Fe2—C7B	39.93 (16)	C16A—C15A—H15A	120.2
C9B—Fe2—C7B	68.19 (16)	N2—C11B—C10B	113.1 (3)
C10B—Fe2—C7B	68.36 (15)	N2—C11B—H11C	109
C2B—Fe2—C7B	116.37 (19)	C10B—C11B—H11C	109
C5B—Fe2—C8B	175.0 (3)	N2—C11B—H11D	109
C1B—Fe2—C8B	136.1 (2)	C10B—C11B—H11D	109
C4B—Fe2—C8B	143.6 (3)	H11C—C11B—H11D	107.8
C3B—Fe2—C8B	116.1 (2)	C14B—C19B—C18B	119.3 (4)
C6B—Fe2—C8B	67.48 (17)	C14B—C19B—H19B	120.3
C9B—Fe2—C8B	40.60 (15)	C18B—C19B—H19B	120.3
C10B—Fe2—C8B	68.47 (14)	C17B—C16B—C15B	120.3 (4)
C2B—Fe2—C8B	112.73 (17)	C17B—C16B—H16B	119.8
C7B—Fe2—C8B	40.24 (17)	C15B—C16B—H16B	119.8
C9A—Fe1—C5A	107.14 (17)	C6B—C7B—C8B	108.2 (4)
C9A—Fe1—C10A	41.06 (13)	C6B—C7B—Fe2	69.8 (2)
C5A—Fe1—C10A	114.86 (16)	C8B—C7B—Fe2	70.0 (2)
C9A—Fe1—C1A	128.96 (18)	C6B—C7B—H7B	125.9
C5A—Fe1—C1A	40.85 (17)	C8B—C7B—H7B	125.9
C10A—Fe1—C1A	106.73 (15)	Fe2—C7B—H7B	125.9
C9A—Fe1—C6A	68.28 (14)	C16B—C17B—C18B	119.3 (4)
C5A—Fe1—C6A	148.24 (17)	C16B—C17B—H17B	120.3
C10A—Fe1—C6A	40.66 (13)	C18B—C17B—H17B	120.3
C1A—Fe1—C6A	116.23 (16)	C12B—C13B—H13D	109.5
C9A—Fe1—C4A	116.56 (15)	C12B—C13B—H13E	109.5
C5A—Fe1—C4A	40.48 (16)	H13D—C13B—H13E	109.5
C10A—Fe1—C4A	148.34 (15)	C12B—C13B—H13F	109.5
C1A—Fe1—C4A	68.09 (16)	H13D—C13B—H13F	109.5
C6A—Fe1—C4A	170.28 (15)	H13E—C13B—H13F	109.5
C9A—Fe1—C8A	40.21 (15)	C17B—C18B—C19B	121.0 (4)
C5A—Fe1—C8A	129.55 (19)	C17B—C18B—H18B	119.5
C10A—Fe1—C8A	68.57 (14)	C19B—C18B—H18B	119.5
C1A—Fe1—C8A	167.65 (19)	C17A—C18A—C19A	120.2 (4)
C6A—Fe1—C8A	68.23 (15)	C17A—C18A—H18A	119.9
C4A—Fe1—C8A	109.49 (16)	C19A—C18A—H18A	119.9
C9A—Fe1—C2A	167.78 (16)	O2—C12B—N2	121.2 (4)
C5A—Fe1—C2A	68.18 (17)	O2—C12B—C13B	121.8 (4)
C10A—Fe1—C2A	129.41 (14)	N2—C12B—C13B	117.1 (4)
C1A—Fe1—C2A	40.30 (16)	C12A—C13A—H13A	109.5
C6A—Fe1—C2A	109.33 (15)	C12A—C13A—H13B	109.5
C4A—Fe1—C2A	67.81 (15)	H13A—C13A—H13B	109.5
C8A—Fe1—C2A	151.25 (17)	C12A—C13A—H13C	109.5
C9A—Fe1—C7A	67.68 (16)	H13A—C13A—H13C	109.5
C5A—Fe1—C7A	168.53 (18)	H13B—C13A—H13C	109.5
C10A—Fe1—C7A	68.54 (14)	C1B—C5B—C4B	106.4 (5)
C1A—Fe1—C7A	150.29 (18)	C1B—C5B—Fe2	70.0 (3)
C6A—Fe1—C7A	40.89 (14)	C4B—C5B—Fe2	69.9 (3)
C4A—Fe1—C7A	131.44 (16)	C1B—C5B—H5B	126.8
C8A—Fe1—C7A	40.06 (16)	C4B—C5B—H5B	126.8
C2A—Fe1—C7A	118.96 (16)	Fe2—C5B—H5B	124.9
C9A—Fe1—C3A	149.96 (15)	O1—C12A—N1	121.0 (4)
C5A—Fe1—C3A	67.63 (16)	O1—C12A—C13A	121.3 (4)
C10A—Fe1—C3A	168.82 (14)	N1—C12A—C13A	117.7 (3)
C1A—Fe1—C3A	67.51 (16)	C2B—C3B—C4B	110.1 (5)
C6A—Fe1—C3A	132.00 (14)	C2B—C3B—Fe2	71.1 (3)
C4A—Fe1—C3A	40.00 (14)	C4B—C3B—Fe2	70.1 (3)
C8A—Fe1—C3A	119.04 (16)	C2B—C3B—H3B	124.9
C2A—Fe1—C3A	40.14 (14)	C4B—C3B—H3B	124.9
C7A—Fe1—C3A	111.33 (15)	Fe2—C3B—H3B	125.4
C19A—C14A—C15A	119.4 (3)	C18A—C17A—C16A	119.3 (4)
C19A—C14A—N1	120.8 (3)	C18A—C17A—H17A	120.3
C15A—C14A—N1	119.8 (3)	C16A—C17A—H17A	120.3
C12B—N2—C14B	124.7 (3)	C3B—C2B—C1B	108.7 (5)
C12B—N2—C11B	118.9 (3)	C3B—C2B—Fe2	70.5 (3)
C14B—N2—C11B	116.2 (3)	C1B—C2B—Fe2	69.2 (3)
C6B—C10B—C9B	106.6 (3)	C3B—C2B—H2B	125.6
C6B—C10B—C11B	127.5 (3)	C1B—C2B—H2B	125.6
C9B—C10B—C11B	125.8 (3)	Fe2—C2B—H2B	126.2
C6B—C10B—Fe2	69.5 (2)	C3B—C4B—C5B	106.7 (5)
C9B—C10B—Fe2	69.42 (19)	C3B—C4B—Fe2	71.0 (3)
C11B—C10B—Fe2	125.9 (2)	C5B—C4B—Fe2	68.9 (3)
C12A—N1—C14A	124.2 (3)	C3B—C4B—H4B	126.6
C12A—N1—C11A	118.7 (3)	C5B—C4B—H4B	126.6
C14A—N1—C11A	116.9 (3)	Fe2—C4B—H4B	125
C4A—C3A—C2A	108.8 (4)	C10A—C6A—C7A	108.0 (3)
C4A—C3A—Fe1	69.8 (2)	C10A—C6A—Fe1	69.60 (19)
C2A—C3A—Fe1	69.8 (2)	C7A—C6A—Fe1	70.0 (2)
C4A—C3A—H3A	125.6	C10A—C6A—H6A	126
C2A—C3A—H3A	125.6	C7A—C6A—H6A	126
Fe1—C3A—H3A	126.4	Fe1—C6A—H6A	126
C6A—C10A—C9A	107.0 (3)	C8A—C9A—C10A	108.8 (3)
C6A—C10A—C11A	126.2 (3)	C8A—C9A—Fe1	70.6 (2)
C9A—C10A—C11A	126.8 (3)	C10A—C9A—Fe1	69.61 (19)
C6A—C10A—Fe1	69.74 (18)	C8A—C9A—H9A	125.6
C9A—C10A—Fe1	69.32 (19)	C10A—C9A—H9A	125.6
C11A—C10A—Fe1	124.6 (2)	Fe1—C9A—H9A	125.8
C8A—C7A—C6A	108.1 (3)	C1A—C2A—C3A	107.6 (3)
C8A—C7A—Fe1	70.0 (2)	C1A—C2A—Fe1	69.4 (2)
C6A—C7A—Fe1	69.1 (2)	C3A—C2A—Fe1	70.0 (2)
C8A—C7A—H7A	126	C1A—C2A—H2A	126.2
C6A—C7A—H7A	126	C3A—C2A—H2A	126.2
Fe1—C7A—H7A	126.6	Fe1—C2A—H2A	126
C2B—C1B—C5B	108.1 (5)	C9A—C8A—C7A	108.1 (3)
C2B—C1B—Fe2	71.6 (3)	C9A—C8A—Fe1	69.2 (2)
C5B—C1B—Fe2	69.8 (3)	C7A—C8A—Fe1	70.0 (2)
C2B—C1B—H1B	126	C9A—C8A—H8A	125.9
C5B—C1B—H1B	126	C7A—C8A—H8A	125.9
Fe2—C1B—H1B	124.3	Fe1—C8A—H8A	126.5
C19B—C14B—C15B	120.2 (4)	C3A—C4A—C5A	107.8 (4)
C19B—C14B—N2	119.4 (3)	C3A—C4A—Fe1	70.2 (2)
C15B—C14B—N2	120.3 (3)	C5A—C4A—Fe1	69.2 (2)
N1—C11A—C10A	113.1 (3)	C3A—C4A—H4A	126.1
N1—C11A—H11A	109	C5A—C4A—H4A	126.1
C10A—C11A—H11A	109	Fe1—C4A—H4A	126.1
N1—C11A—H11B	109	C2A—C1A—C5A	108.0 (4)
C10A—C11A—H11B	109	C2A—C1A—Fe1	70.3 (2)
H11A—C11A—H11B	107.8	C5A—C1A—Fe1	69.4 (2)
C4A—C5A—C1A	107.7 (4)	C2A—C1A—H1A	126
C4A—C5A—Fe1	70.3 (2)	C5A—C1A—H1A	126
C1A—C5A—Fe1	69.7 (2)	Fe1—C1A—H1A	125.8

C19A—C14A—N1—C12A	110.5 (4)	C2B—C1B—C5B—C4B	−0.8 (5)
C15A—C14A—N1—C12A	−71.6 (5)	Fe2—C1B—C5B—C4B	60.8 (3)
C19A—C14A—N1—C11A	−75.3 (4)	C2B—C1B—C5B—Fe2	−61.7 (3)
C15A—C14A—N1—C11A	102.6 (4)	C14A—N1—C12A—O1	173.5 (3)
C12B—N2—C14B—C19B	84.9 (5)	C11A—N1—C12A—O1	−0.6 (5)
C11B—N2—C14B—C19B	−89.9 (4)	C14A—N1—C12A—C13A	−7.0 (5)
C12B—N2—C14B—C15B	−98.1 (4)	C11A—N1—C12A—C13A	178.9 (3)
C11B—N2—C14B—C15B	87.2 (4)	C19A—C18A—C17A—C16A	0.3 (7)
C12A—N1—C11A—C10A	−92.1 (4)	C15A—C16A—C17A—C18A	−1.6 (8)
C14A—N1—C11A—C10A	93.3 (4)	C4B—C3B—C2B—C1B	−0.6 (5)
C6A—C10A—C11A—N1	93.3 (4)	Fe2—C3B—C2B—C1B	58.9 (3)
C9A—C10A—C11A—N1	−88.7 (4)	C4B—C3B—C2B—Fe2	−59.5 (3)
Fe1—C10A—C11A—N1	−177.6 (2)	C5B—C1B—C2B—C3B	0.9 (5)
C6B—C10B—C9B—C8B	0.0 (4)	Fe2—C1B—C2B—C3B	−59.7 (3)
C11B—C10B—C9B—C8B	−180.0 (3)	C5B—C1B—C2B—Fe2	60.6 (3)
Fe2—C10B—C9B—C8B	−59.9 (2)	C2B—C3B—C4B—C5B	0.1 (5)
C6B—C10B—C9B—Fe2	59.8 (2)	Fe2—C3B—C4B—C5B	−60.0 (3)
C11B—C10B—C9B—Fe2	−120.1 (3)	C2B—C3B—C4B—Fe2	60.1 (3)
C9B—C10B—C6B—C7B	−0.4 (4)	C1B—C5B—C4B—C3B	0.5 (5)
C11B—C10B—C6B—C7B	179.6 (3)	Fe2—C5B—C4B—C3B	61.3 (3)
Fe2—C10B—C6B—C7B	59.4 (3)	C1B—C5B—C4B—Fe2	−60.8 (3)
C9B—C10B—C6B—Fe2	−59.8 (2)	C9A—C10A—C6A—C7A	0.1 (4)
C11B—C10B—C6B—Fe2	120.2 (3)	C11A—C10A—C6A—C7A	178.4 (3)
C10B—C9B—C8B—C7B	0.4 (4)	Fe1—C10A—C6A—C7A	59.7 (2)
Fe2—C9B—C8B—C7B	−59.1 (3)	C9A—C10A—C6A—Fe1	−59.6 (2)
C10B—C9B—C8B—Fe2	59.6 (2)	C11A—C10A—C6A—Fe1	118.7 (3)
C19B—C14B—C15B—C16B	0.9 (6)	C8A—C7A—C6A—C10A	−0.1 (4)
N2—C14B—C15B—C16B	−176.2 (4)	Fe1—C7A—C6A—C10A	−59.4 (2)
C15A—C14A—C19A—C18A	−1.7 (6)	C8A—C7A—C6A—Fe1	59.3 (2)
N1—C14A—C19A—C18A	176.3 (4)	C6A—C10A—C9A—C8A	0.0 (4)
C19A—C14A—C15A—C16A	0.3 (7)	C11A—C10A—C9A—C8A	−178.3 (3)
N1—C14A—C15A—C16A	−177.7 (4)	Fe1—C10A—C9A—C8A	−59.9 (3)
C17A—C16A—C15A—C14A	1.3 (8)	C6A—C10A—C9A—Fe1	59.9 (2)
C12B—N2—C11B—C10B	91.5 (4)	C11A—C10A—C9A—Fe1	−118.4 (3)
C14B—N2—C11B—C10B	−93.3 (4)	C4A—C3A—C2A—C1A	0.4 (4)
C6B—C10B—C11B—N2	82.3 (5)	Fe1—C3A—C2A—C1A	59.4 (2)
C9B—C10B—C11B—N2	−97.7 (4)	C4A—C3A—C2A—Fe1	−59.1 (2)
Fe2—C10B—C11B—N2	173.0 (2)	C10A—C9A—C8A—C7A	−0.1 (4)
C15B—C14B—C19B—C18B	0.3 (6)	Fe1—C9A—C8A—C7A	−59.4 (3)
N2—C14B—C19B—C18B	177.3 (4)	C10A—C9A—C8A—Fe1	59.3 (2)
C14B—C15B—C16B—C17B	−1.1 (6)	C6A—C7A—C8A—C9A	0.1 (4)
C10B—C6B—C7B—C8B	0.7 (4)	Fe1—C7A—C8A—C9A	58.9 (3)
Fe2—C6B—C7B—C8B	59.7 (3)	C6A—C7A—C8A—Fe1	−58.8 (2)
C10B—C6B—C7B—Fe2	−59.0 (2)	C2A—C3A—C4A—C5A	−0.2 (4)
C9B—C8B—C7B—C6B	−0.7 (4)	Fe1—C3A—C4A—C5A	−59.2 (3)
Fe2—C8B—C7B—C6B	−59.5 (3)	C2A—C3A—C4A—Fe1	59.1 (2)
C9B—C8B—C7B—Fe2	58.9 (3)	C1A—C5A—C4A—C3A	−0.1 (4)
C15B—C16B—C17B—C18B	0.2 (6)	Fe1—C5A—C4A—C3A	59.8 (3)
C16B—C17B—C18B—C19B	0.9 (7)	C1A—C5A—C4A—Fe1	−59.9 (3)
C14B—C19B—C18B—C17B	−1.2 (6)	C3A—C2A—C1A—C5A	−0.4 (4)
C14A—C19A—C18A—C17A	1.4 (7)	Fe1—C2A—C1A—C5A	59.4 (3)
C14B—N2—C12B—O2	−177.5 (4)	C3A—C2A—C1A—Fe1	−59.8 (2)
C11B—N2—C12B—O2	−2.9 (6)	C4A—C5A—C1A—C2A	0.3 (4)
C14B—N2—C12B—C13B	2.5 (6)	Fe1—C5A—C1A—C2A	−60.0 (3)
C11B—N2—C12B—C13B	177.2 (3)	C4A—C5A—C1A—Fe1	60.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15A—H15A···O1ⁱ	0.93	2.56	3.456 (5)	162
C19B—H19B···O2ⁱⁱ	0.93	2.55	3.421 (5)	157
C15A—H15A···O1ⁱ	0.93	2.56	3.456 (5)	162
C19B—H19B···O2ⁱⁱ	0.93	2.55	3.421 (5)	157

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

Acknowledgements

This research was financed by the Laboratory of Valorization and Promotion of Saharan resources (project No. E03220080002). The authors acknowledge the assistance of Merazig Hocine for the data collection.

References

Ahmedi, R. & Lanez, T. (2011). J. Fundam. Appl. Sci. 3, 183–193. CrossRef Google Scholar
Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343–350. CrossRef Web of Science IUCr Journals Google Scholar
Chavain, N., Davioud-Charvet, E., Trivelli, X., Mbeki, L., Rottmann, M., Brun, R. & Biot, C. (2009). Bioorg. Med. Chem. 17, 8048–8059. Web of Science CSD CrossRef PubMed CAS Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Khand, I. U., Lanez, T. & Pauson, P. L. (1989). J. Chem. Soc. Perkin Trans. 1, pp. 2075–2078. CrossRef Web of Science Google Scholar
Khelef, A. & Lanez, T. (2015). Der Pharma Chem. 7, 318–323. CAS Google Scholar
Khelef, A., Terki, B., Mahboub, M. S. & Lanez, T. (2012). Acta Cryst. E68, m647. CSD CrossRef IUCr Journals Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands. Google Scholar
Osgerby, J. M. & Pauson, P. L. (1961). J. Chem. Soc. pp. 4600–4604. CrossRef Web of Science Google Scholar
Rahim, O., Khelef, A., Terki, B., Mahboub, M. S. & Lanez, T. (2012). Acta Cryst. E68, m1318. CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Szarka, Z., Kuik, Á., Skoda-Földes, R. & Kollár, L. (2004). J. Organomet. Chem. 689, 2770–2775. Web of Science CrossRef CAS Google Scholar
Torres, J. C., Pilli, R. A., Vargas, M. D. A., Violante, F., Garden, S. J. & Pinto, A. C. (2002). Tetrahedron, 58, 4487–4492. Web of Science CrossRef CAS Google Scholar
Uno, M. & Dixneuf, P. H. (1998). Angew. Chem. Int. Ed. 37, 1714–1717. CrossRef CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.