metal-organic compounds
N-Ferrocenymethyl-N-phenylacetamide
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
In the title compound, [Fe(C5H5)(C14H14NO)], the 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.
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), (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 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].
of title compound comprises two crystallographically independent molecules,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.
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 .
details are summarized in Table 2Structural data
CCDC reference: 1451430
https://doi.org/10.1107/S2414314616002030/sj5494sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314616002030/sj5494Isup2.hkl
a new https://doi.org/10.1107/S2414314616002030/sj5494sup3.txt
DOI: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).
[Fe(C5H5)(C14H14NO)] | Z = 4 |
Mr = 333.2 | F(000) = 696 |
Triclinic, P1 | Dx = 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 |
Nonius KappaCCD diffractometer | Rint = 0.039 |
Radiation source: fine-focus sealed tube | θmax = 24.7°, θmin = 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 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(Fo2) + (0.0489P)2 + 0.6059P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.115 | (Δ/σ)max = 0.001 |
S = 1.02 | Δρmax = 0.37 e Å−3 |
5157 reflections | Δρmin = −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 |
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. |
x | y | z | Uiso*/Ueq | ||
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* |
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) |
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) |
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
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