metal-organic compounds
6-Benzyl-2-methyl-1,3-bis(pentafluorophenyl)-1,3,6,2-triazaalumocane
aDepartment of Chemistry, M.V. Lomonosov Moscow State University, Leninskie Gory 1/3, Moscow 119991, Russian Federation, and bInstitute of General and Inorganic Chemistry, Russian Academy of Sciences, Leninskii prosp. 31, Moscow 119991, Russian Federation
*Correspondence e-mail: churakov@igic.ras.ru
In the title compound, [Al(CH3)(C23H15F10N3)], the AlIII atom is coordinated in a distorted tetrahedral geometry by three N atoms from the tridentate amine and by one C atom of the methyl substituent. Further, there is a short intramolecular Al⋯F contact [2.5717 (11) Å], leading to an overall distorted trigonal–bipyramidal coordination environment around AlIII.
Related literature
For general background to the chemistry affording the tridentate ligand N-benzyl-N′-(pentafluorophenyl)-N-{2-[(pentafluorophenyl)amino]ethyl}ethane-1,2-diamine, see: Lermontova et al. (2009). Complexes of germanium and tin based on that and the related ligands and their X-ray structures have been described by Huang et al. (2011, 2012). For related structures having short Al⋯F—C contacts, see: Smith et al. (2010); Jansen & Mokros (1992). For a description of the Cambridge Structural Database, see: Allen (2002).
Experimental
Crystal data
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Data collection: APEX2 (Bruker, 2008); cell SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
Supporting information
A solution of 0.26 g (0.50 mmol) of BnN(CH2CH2NHC6F5)2 (Lermontova et al., 2009) in toluene (10 ml) was added dropwise to a solution of 0.25 ml (0.50 mmol) of Me3Al in toluene (10 ml) under stirring at 243 K. The reaction mixture was allowed to warm to room temperature and stirred overnight. The volatiles were removed under vacuum. The residue was washed by ether (3×5 ml) and dried to give 0.24 g (86%) of BnN(CH2CH2NHC6F5)2AlMe as a white solid.
1H NMR (CDCl3): δ -0.56 (br s, 3H, AlMe); 2.88–2.97, 3.00–3.09, 3.57–3.66, 3.67–3.76 (4 m, 8H, NCH2); 4.03 (s, 2H, NCH2Ph); 7.29–7.34, 7.42–7.47 (2 m, 5H, Ph). 13C NMR (CDCl3): δ 44.29, 49.94 (4NCH2); 56.01 (NCH2Ph); 128.77, 129.00, 131.39, 131.55 (Ph). 1H NMR (C6D6): δ -0.31 (p, JF—H = 2.4 Hz, 3H, AlMe); 1.95–2.04, 2.10–2.17, 3.08–3.20 (3 m, 8H, NCH2); 3.34 (s, 2H, NCH2Ph); 6.53–6.57, 7.00–7.06, 7.07–7.10 (3 m, 5H, Ph). 13C NMR (C6D6): δ 49.48, 53.34 (4NCH2); 55.61 (NCH2Ph); 128.54, 129.24, 129.31, 131.72 (Ph). EI m/z 564 (M, 5%); 432 (M—Bn, 3%); 91 (Bn, 100%); 42 (AlMe, 78%). Anal. Calcd. for C24H18AlN3F10: C 50.98, H 3.21, N 7.43. Found: C 50.68, H 3.36, N 7.39.
The crystals were obtained from the concentrated toluene solution under storing at 255 K for several days.
All H atoms were located in a difference Fourier map and refined isotropically. [Refined C—H distances: 0.90 (2)–0.97 (3) Å for aromatic CH, 0.931 (19)–1.004 (19) Å for CH2 and 0.92 (3)–0.98 (2) Å for CH3.]
Data collection: APEX2 (Bruker, 2008); cell
SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).[Al(CH3)(C23H15F10N3)] | F(000) = 1144 |
Mr = 565.39 | Dx = 1.641 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 8521 reflections |
a = 7.9530 (14) Å | θ = 2.5–28.1° |
b = 33.577 (6) Å | µ = 0.19 mm−1 |
c = 8.7247 (15) Å | T = 173 K |
β = 100.809 (2)° | Plate, colourless |
V = 2288.5 (7) Å3 | 0.20 × 0.20 × 0.05 mm |
Z = 4 |
Bruker SMART APEXII diffractometer | 4972 independent reflections |
Radiation source: fine-focus sealed tube | 4317 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.021 |
ω scans | θmax = 27.0°, θmin = 2.4° |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | h = −10→10 |
Tmin = 0.963, Tmax = 0.991 | k = −42→42 |
19211 measured reflections | l = −11→11 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.036 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.094 | All H-atom parameters refined |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0439P)2 + 1.3304P] where P = (Fo2 + 2Fc2)/3 |
4972 reflections | (Δ/σ)max < 0.001 |
415 parameters | Δρmax = 0.36 e Å−3 |
0 restraints | Δρmin = −0.26 e Å−3 |
[Al(CH3)(C23H15F10N3)] | V = 2288.5 (7) Å3 |
Mr = 565.39 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 7.9530 (14) Å | µ = 0.19 mm−1 |
b = 33.577 (6) Å | T = 173 K |
c = 8.7247 (15) Å | 0.20 × 0.20 × 0.05 mm |
β = 100.809 (2)° |
Bruker SMART APEXII diffractometer | 4972 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | 4317 reflections with I > 2σ(I) |
Tmin = 0.963, Tmax = 0.991 | Rint = 0.021 |
19211 measured reflections |
R[F2 > 2σ(F2)] = 0.036 | 0 restraints |
wR(F2) = 0.094 | All H-atom parameters refined |
S = 1.02 | Δρmax = 0.36 e Å−3 |
4972 reflections | Δρmin = −0.26 e Å−3 |
415 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Al1 | 0.55982 (6) | 0.117782 (13) | 0.49859 (5) | 0.02089 (11) | |
N1 | 0.60780 (16) | 0.16461 (4) | 0.39907 (14) | 0.0223 (3) | |
N2 | 0.68539 (17) | 0.07207 (4) | 0.47836 (15) | 0.0254 (3) | |
N3 | 0.74288 (16) | 0.13396 (4) | 0.67940 (14) | 0.0214 (3) | |
C1 | 0.6675 (2) | 0.15076 (5) | 0.81197 (18) | 0.0247 (3) | |
C2 | 0.7938 (2) | 0.16032 (5) | 0.95983 (18) | 0.0267 (3) | |
C3 | 0.8602 (2) | 0.19843 (5) | 0.9886 (2) | 0.0308 (4) | |
C4 | 0.9723 (2) | 0.20708 (6) | 1.1272 (2) | 0.0375 (4) | |
C5 | 1.0209 (2) | 0.17743 (7) | 1.2368 (2) | 0.0408 (5) | |
C6 | 0.9549 (3) | 0.13976 (7) | 1.2102 (2) | 0.0407 (5) | |
C7 | 0.8404 (2) | 0.13109 (6) | 1.0735 (2) | 0.0340 (4) | |
C10 | 0.3337 (2) | 0.11830 (6) | 0.5555 (2) | 0.0304 (4) | |
C11 | 0.84769 (19) | 0.16404 (5) | 0.61234 (18) | 0.0236 (3) | |
C12 | 0.7313 (2) | 0.19083 (5) | 0.49746 (18) | 0.0232 (3) | |
C13 | 0.51390 (18) | 0.17824 (5) | 0.26115 (17) | 0.0212 (3) | |
C14 | 0.4895 (2) | 0.21746 (5) | 0.20674 (18) | 0.0235 (3) | |
C15 | 0.3887 (2) | 0.22716 (5) | 0.06498 (19) | 0.0261 (3) | |
C16 | 0.3087 (2) | 0.19796 (5) | −0.03367 (18) | 0.0279 (3) | |
C17 | 0.3261 (2) | 0.15883 (5) | 0.01513 (18) | 0.0257 (3) | |
C18 | 0.4249 (2) | 0.15007 (5) | 0.15781 (18) | 0.0235 (3) | |
C21 | 0.8424 (2) | 0.09669 (5) | 0.72549 (19) | 0.0258 (3) | |
C22 | 0.8566 (2) | 0.07283 (5) | 0.58014 (19) | 0.0270 (3) | |
C23 | 0.6498 (2) | 0.04053 (5) | 0.37471 (18) | 0.0274 (3) | |
C24 | 0.7699 (2) | 0.01889 (5) | 0.3099 (2) | 0.0338 (4) | |
C25 | 0.7253 (3) | −0.01322 (6) | 0.2104 (2) | 0.0405 (5) | |
C26 | 0.5577 (3) | −0.02420 (5) | 0.1651 (2) | 0.0408 (5) | |
C27 | 0.4342 (3) | −0.00290 (5) | 0.2209 (2) | 0.0371 (4) | |
C28 | 0.4803 (2) | 0.02780 (5) | 0.3244 (2) | 0.0304 (4) | |
F14 | 0.56225 (13) | 0.24841 (3) | 0.29513 (11) | 0.0310 (2) | |
F15 | 0.36334 (13) | 0.26570 (3) | 0.02492 (12) | 0.0354 (2) | |
F16 | 0.21053 (13) | 0.20771 (3) | −0.17192 (11) | 0.0392 (3) | |
F17 | 0.24581 (13) | 0.12973 (3) | −0.07535 (12) | 0.0371 (2) | |
F18 | 0.43879 (13) | 0.11143 (3) | 0.20488 (11) | 0.0309 (2) | |
F24 | 0.93701 (14) | 0.02933 (4) | 0.34006 (13) | 0.0452 (3) | |
F25 | 0.84828 (18) | −0.03270 (4) | 0.15369 (15) | 0.0569 (4) | |
F26 | 0.51315 (19) | −0.05520 (3) | 0.06690 (14) | 0.0553 (4) | |
F27 | 0.26773 (16) | −0.01208 (3) | 0.17435 (14) | 0.0492 (3) | |
F28 | 0.35477 (13) | 0.04643 (3) | 0.37978 (13) | 0.0382 (3) | |
H112 | 0.917 (2) | 0.1790 (5) | 0.6947 (19) | 0.018 (4)* | |
H122 | 0.803 (2) | 0.2058 (5) | 0.436 (2) | 0.020 (4)* | |
H121 | 0.675 (2) | 0.2111 (5) | 0.554 (2) | 0.020 (4)* | |
H222 | 0.894 (2) | 0.0457 (6) | 0.615 (2) | 0.027 (5)* | |
H3 | 0.833 (2) | 0.2184 (5) | 0.912 (2) | 0.025 (4)* | |
H12 | 0.605 (2) | 0.1750 (6) | 0.774 (2) | 0.030 (5)* | |
H111 | 0.921 (2) | 0.1507 (5) | 0.558 (2) | 0.024 (4)* | |
H212 | 0.778 (2) | 0.0818 (5) | 0.790 (2) | 0.028 (5)* | |
H221 | 0.950 (2) | 0.0841 (6) | 0.530 (2) | 0.028 (5)* | |
H11 | 0.585 (2) | 0.1307 (6) | 0.834 (2) | 0.031 (5)* | |
H211 | 0.955 (2) | 0.1031 (6) | 0.787 (2) | 0.029 (5)* | |
H7 | 0.792 (2) | 0.1051 (6) | 1.055 (2) | 0.031 (5)* | |
H103 | 0.310 (3) | 0.1447 (7) | 0.596 (3) | 0.050 (6)* | |
H4 | 1.012 (3) | 0.2322 (7) | 1.140 (2) | 0.036 (5)* | |
H5 | 1.097 (3) | 0.1834 (6) | 1.326 (3) | 0.045 (6)* | |
H102 | 0.322 (3) | 0.0973 (7) | 0.630 (3) | 0.048 (6)* | |
H6 | 0.982 (3) | 0.1182 (7) | 1.285 (3) | 0.060 (7)* | |
H101 | 0.255 (3) | 0.1136 (8) | 0.465 (3) | 0.064 (7)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Al1 | 0.0208 (2) | 0.0198 (2) | 0.0209 (2) | 0.00011 (17) | 0.00084 (17) | 0.00025 (17) |
N1 | 0.0248 (6) | 0.0209 (6) | 0.0193 (6) | −0.0020 (5) | −0.0004 (5) | 0.0001 (5) |
N2 | 0.0265 (7) | 0.0217 (6) | 0.0254 (7) | 0.0034 (5) | −0.0016 (5) | −0.0024 (5) |
N3 | 0.0222 (6) | 0.0213 (6) | 0.0201 (6) | 0.0019 (5) | 0.0022 (5) | −0.0006 (5) |
C1 | 0.0233 (7) | 0.0286 (8) | 0.0216 (7) | 0.0019 (6) | 0.0028 (6) | −0.0012 (6) |
C2 | 0.0231 (7) | 0.0362 (9) | 0.0208 (7) | 0.0034 (6) | 0.0042 (6) | −0.0041 (6) |
C3 | 0.0287 (8) | 0.0338 (9) | 0.0293 (8) | 0.0055 (7) | 0.0038 (7) | −0.0060 (7) |
C4 | 0.0307 (9) | 0.0450 (11) | 0.0368 (10) | −0.0016 (8) | 0.0066 (7) | −0.0164 (8) |
C5 | 0.0278 (9) | 0.0717 (14) | 0.0219 (8) | 0.0035 (9) | 0.0016 (7) | −0.0107 (9) |
C6 | 0.0403 (10) | 0.0600 (13) | 0.0212 (8) | 0.0057 (9) | 0.0042 (7) | 0.0045 (8) |
C7 | 0.0361 (9) | 0.0418 (10) | 0.0242 (8) | 0.0004 (8) | 0.0059 (7) | 0.0013 (7) |
C10 | 0.0238 (8) | 0.0363 (10) | 0.0303 (9) | 0.0002 (7) | 0.0031 (7) | 0.0010 (8) |
C11 | 0.0217 (7) | 0.0258 (8) | 0.0223 (7) | −0.0029 (6) | 0.0020 (6) | −0.0018 (6) |
C12 | 0.0238 (7) | 0.0222 (7) | 0.0230 (7) | −0.0033 (6) | 0.0024 (6) | −0.0022 (6) |
C13 | 0.0200 (7) | 0.0241 (7) | 0.0201 (7) | 0.0002 (6) | 0.0051 (5) | 0.0007 (6) |
C14 | 0.0241 (7) | 0.0227 (7) | 0.0237 (7) | −0.0022 (6) | 0.0049 (6) | −0.0006 (6) |
C15 | 0.0261 (8) | 0.0254 (8) | 0.0273 (8) | 0.0012 (6) | 0.0065 (6) | 0.0075 (6) |
C16 | 0.0229 (7) | 0.0391 (9) | 0.0205 (7) | 0.0007 (7) | 0.0007 (6) | 0.0063 (7) |
C17 | 0.0232 (7) | 0.0313 (8) | 0.0223 (7) | −0.0039 (6) | 0.0034 (6) | −0.0045 (6) |
C18 | 0.0250 (7) | 0.0221 (7) | 0.0236 (7) | 0.0008 (6) | 0.0054 (6) | −0.0003 (6) |
C21 | 0.0262 (8) | 0.0249 (8) | 0.0237 (8) | 0.0044 (6) | −0.0018 (6) | 0.0008 (6) |
C22 | 0.0256 (8) | 0.0256 (8) | 0.0274 (8) | 0.0059 (6) | −0.0017 (6) | −0.0017 (6) |
C23 | 0.0370 (9) | 0.0188 (7) | 0.0238 (8) | 0.0026 (6) | −0.0005 (6) | 0.0020 (6) |
C24 | 0.0374 (9) | 0.0299 (9) | 0.0310 (9) | 0.0079 (7) | −0.0020 (7) | −0.0021 (7) |
C25 | 0.0567 (12) | 0.0293 (9) | 0.0326 (9) | 0.0163 (8) | 0.0013 (8) | −0.0025 (7) |
C26 | 0.0650 (13) | 0.0200 (8) | 0.0313 (9) | 0.0015 (8) | −0.0064 (9) | −0.0029 (7) |
C27 | 0.0492 (11) | 0.0227 (8) | 0.0343 (9) | −0.0062 (8) | −0.0050 (8) | 0.0036 (7) |
C28 | 0.0389 (9) | 0.0200 (8) | 0.0302 (8) | −0.0011 (7) | 0.0008 (7) | 0.0029 (6) |
F14 | 0.0387 (5) | 0.0212 (5) | 0.0299 (5) | −0.0042 (4) | −0.0014 (4) | 0.0004 (4) |
F15 | 0.0387 (6) | 0.0295 (5) | 0.0362 (5) | 0.0026 (4) | 0.0024 (4) | 0.0130 (4) |
F16 | 0.0365 (6) | 0.0502 (7) | 0.0257 (5) | −0.0025 (5) | −0.0074 (4) | 0.0107 (5) |
F17 | 0.0392 (6) | 0.0393 (6) | 0.0286 (5) | −0.0072 (4) | −0.0045 (4) | −0.0082 (4) |
F18 | 0.0384 (5) | 0.0214 (5) | 0.0300 (5) | −0.0022 (4) | −0.0009 (4) | −0.0010 (4) |
F24 | 0.0363 (6) | 0.0525 (7) | 0.0453 (6) | 0.0106 (5) | 0.0041 (5) | −0.0165 (5) |
F25 | 0.0693 (8) | 0.0504 (7) | 0.0465 (7) | 0.0275 (6) | −0.0010 (6) | −0.0186 (6) |
F26 | 0.0880 (10) | 0.0271 (6) | 0.0431 (7) | 0.0011 (6) | −0.0074 (6) | −0.0131 (5) |
F27 | 0.0533 (7) | 0.0347 (6) | 0.0531 (7) | −0.0174 (5) | −0.0067 (6) | −0.0040 (5) |
F28 | 0.0328 (5) | 0.0360 (6) | 0.0452 (6) | −0.0056 (4) | 0.0054 (5) | −0.0057 (5) |
Al1—N2 | 1.8575 (14) | C11—H111 | 0.931 (19) |
Al1—N1 | 1.8697 (14) | C12—H122 | 0.990 (17) |
Al1—C10 | 1.9536 (18) | C12—H121 | 0.995 (17) |
Al1—N3 | 2.0104 (13) | C13—C14 | 1.401 (2) |
Al1—F18 | 2.5717 (11) | C13—C18 | 1.403 (2) |
N1—C13 | 1.3704 (19) | C14—F14 | 1.3573 (17) |
N1—C12 | 1.4700 (19) | C14—C15 | 1.381 (2) |
N2—C23 | 1.387 (2) | C15—F15 | 1.3457 (18) |
N2—C22 | 1.480 (2) | C15—C16 | 1.379 (2) |
N3—C21 | 1.4947 (19) | C16—F16 | 1.3486 (18) |
N3—C11 | 1.497 (2) | C16—C17 | 1.380 (2) |
N3—C1 | 1.5086 (19) | C17—F17 | 1.3404 (18) |
C1—C2 | 1.514 (2) | C17—C18 | 1.373 (2) |
C1—H12 | 0.976 (19) | C18—F18 | 1.3591 (18) |
C1—H11 | 0.99 (2) | C21—C22 | 1.522 (2) |
C2—C3 | 1.389 (2) | C21—H212 | 0.972 (19) |
C2—C7 | 1.395 (2) | C21—H211 | 0.980 (19) |
C3—C4 | 1.392 (2) | C22—H222 | 0.987 (19) |
C3—H3 | 0.946 (19) | C22—H221 | 1.004 (19) |
C4—C5 | 1.384 (3) | C23—C24 | 1.401 (2) |
C4—H4 | 0.90 (2) | C23—C28 | 1.404 (2) |
C5—C6 | 1.372 (3) | C24—F24 | 1.352 (2) |
C5—H5 | 0.91 (2) | C24—C25 | 1.388 (3) |
C6—C7 | 1.390 (3) | C25—F25 | 1.345 (2) |
C6—H6 | 0.97 (3) | C25—C26 | 1.368 (3) |
C7—H7 | 0.96 (2) | C26—F26 | 1.353 (2) |
C10—H103 | 0.98 (2) | C26—C27 | 1.375 (3) |
C10—H102 | 0.98 (2) | C27—F27 | 1.346 (2) |
C10—H101 | 0.92 (3) | C27—C28 | 1.374 (2) |
C11—C12 | 1.524 (2) | C28—F28 | 1.342 (2) |
C11—H112 | 0.963 (17) | ||
N2—Al1—N1 | 119.38 (6) | H112—C11—H111 | 107.5 (14) |
N2—Al1—C10 | 124.64 (7) | N1—C12—C11 | 106.70 (12) |
N1—Al1—C10 | 112.86 (7) | N1—C12—H122 | 112.0 (10) |
N2—Al1—N3 | 88.55 (6) | C11—C12—H122 | 108.6 (10) |
N1—Al1—N3 | 87.50 (6) | N1—C12—H121 | 112.8 (10) |
C10—Al1—N3 | 111.33 (7) | C11—C12—H121 | 110.5 (10) |
N2—Al1—F18 | 86.80 (5) | H122—C12—H121 | 106.2 (14) |
N1—Al1—F18 | 71.20 (4) | N1—C13—C14 | 129.02 (14) |
C10—Al1—F18 | 93.65 (6) | N1—C13—C18 | 117.72 (14) |
N3—Al1—F18 | 152.24 (5) | C14—C13—C18 | 113.25 (13) |
C13—N1—C12 | 120.47 (12) | F14—C14—C15 | 116.26 (14) |
C13—N1—Al1 | 124.31 (10) | F14—C14—C13 | 120.67 (13) |
C12—N1—Al1 | 113.87 (9) | C15—C14—C13 | 123.05 (14) |
C23—N2—C22 | 117.19 (13) | F15—C15—C16 | 119.51 (14) |
C23—N2—Al1 | 130.18 (11) | F15—C15—C14 | 119.53 (14) |
C22—N2—Al1 | 112.29 (10) | C16—C15—C14 | 120.92 (15) |
C21—N3—C11 | 111.39 (12) | F16—C16—C15 | 120.50 (15) |
C21—N3—C1 | 111.92 (12) | F16—C16—C17 | 120.99 (15) |
C11—N3—C1 | 112.20 (12) | C15—C16—C17 | 118.46 (14) |
C21—N3—Al1 | 104.70 (9) | F17—C17—C18 | 120.41 (15) |
C11—N3—Al1 | 104.48 (9) | F17—C17—C16 | 120.21 (14) |
C1—N3—Al1 | 111.67 (9) | C18—C17—C16 | 119.37 (14) |
N3—C1—C2 | 115.91 (12) | F18—C18—C17 | 118.59 (13) |
N3—C1—H12 | 107.5 (11) | F18—C18—C13 | 116.52 (13) |
C2—C1—H12 | 109.0 (11) | C17—C18—C13 | 124.89 (15) |
N3—C1—H11 | 105.8 (11) | N3—C21—C22 | 109.57 (12) |
C2—C1—H11 | 109.8 (11) | N3—C21—H212 | 106.1 (11) |
H12—C1—H11 | 108.7 (15) | C22—C21—H212 | 110.1 (11) |
C3—C2—C7 | 118.60 (15) | N3—C21—H211 | 110.3 (11) |
C3—C2—C1 | 121.23 (15) | C22—C21—H211 | 111.8 (11) |
C7—C2—C1 | 120.12 (16) | H212—C21—H211 | 108.7 (15) |
C2—C3—C4 | 120.60 (18) | N2—C22—C21 | 107.78 (13) |
C2—C3—H3 | 119.8 (11) | N2—C22—H222 | 111.0 (10) |
C4—C3—H3 | 119.5 (11) | C21—C22—H222 | 107.3 (11) |
C5—C4—C3 | 120.01 (19) | N2—C22—H221 | 114.4 (10) |
C5—C4—H4 | 122.9 (13) | C21—C22—H221 | 110.1 (11) |
C3—C4—H4 | 117.1 (13) | H222—C22—H221 | 106.0 (15) |
C6—C5—C4 | 119.88 (17) | N2—C23—C24 | 126.01 (16) |
C6—C5—H5 | 121.3 (14) | N2—C23—C28 | 120.22 (15) |
C4—C5—H5 | 118.9 (14) | C24—C23—C28 | 113.77 (15) |
C5—C6—C7 | 120.41 (19) | F24—C24—C25 | 116.72 (16) |
C5—C6—H6 | 123.0 (15) | F24—C24—C23 | 120.44 (15) |
C7—C6—H6 | 116.6 (15) | C25—C24—C23 | 122.82 (17) |
C6—C7—C2 | 120.45 (19) | F25—C25—C26 | 119.94 (17) |
C6—C7—H7 | 121.0 (12) | F25—C25—C24 | 119.32 (19) |
C2—C7—H7 | 118.6 (12) | C26—C25—C24 | 120.70 (18) |
Al1—C10—H103 | 109.9 (13) | F26—C26—C25 | 121.03 (19) |
Al1—C10—H102 | 111.6 (13) | F26—C26—C27 | 120.31 (18) |
H103—C10—H102 | 111.6 (19) | C25—C26—C27 | 118.66 (16) |
Al1—C10—H101 | 106.8 (16) | F27—C27—C28 | 119.72 (18) |
H103—C10—H101 | 108 (2) | F27—C27—C26 | 120.11 (16) |
H102—C10—H101 | 108 (2) | C28—C27—C26 | 120.17 (18) |
N3—C11—C12 | 109.96 (12) | F28—C28—C27 | 117.51 (16) |
N3—C11—H112 | 110.2 (10) | F28—C28—C23 | 118.72 (14) |
C12—C11—H112 | 112.0 (10) | C27—C28—C23 | 123.77 (17) |
N3—C11—H111 | 108.8 (11) | C18—F18—Al1 | 102.48 (8) |
C12—C11—H111 | 108.3 (11) |
Experimental details
Crystal data | |
Chemical formula | [Al(CH3)(C23H15F10N3)] |
Mr | 565.39 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 173 |
a, b, c (Å) | 7.9530 (14), 33.577 (6), 8.7247 (15) |
β (°) | 100.809 (2) |
V (Å3) | 2288.5 (7) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.19 |
Crystal size (mm) | 0.20 × 0.20 × 0.05 |
Data collection | |
Diffractometer | Bruker SMART APEXII diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2008) |
Tmin, Tmax | 0.963, 0.991 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 19211, 4972, 4317 |
Rint | 0.021 |
(sin θ/λ)max (Å−1) | 0.639 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.036, 0.094, 1.02 |
No. of reflections | 4972 |
No. of parameters | 415 |
H-atom treatment | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 0.36, −0.26 |
Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXTL (Sheldrick, 2008).
Acknowledgements
This work was partially supported by RFBR (projects 12–03-90020-Bel_a, 12–03-00206 − a) and a grant from the President of the Russian Federation to support the research of young Russian scientists and doctors (MD-3634.2012.3).
References
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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.
As a part of our investigation on chemistry of germanium, tin and aluminium complexes based on tridentate ligands (Lermontova et al., 2009; Huang et al., 2011, 2012) we obtained and studied the structure of title compound, [Al[C6H5CH2N(CH2CH2NHC6F5)2](CH3)].
The aluminium centre and aromatic F18 atom form a short intramolecular contact [2.5717 (11) Å]. Of interest, F18—C18 bond length [1.359 (2) Å] is the longest among ten F—C distances in the structure. Analysis of Cambridge Structural Database (ver. 5.33, August 2012; Allen, 2002) shows that similar but somewhat longer Al···F—C contacts are observed in the structures EKIBIK (2.690 Å, Smith et al., 2010) and YADTEC (2.719 Å, Jansen & Mokros, 1992).
The Al1 atom has trigonal bipyramid coordination environment. Three equatorial positions are occupied by methyl group C10 and trigonal nitrogen atoms N1 and N2. The angles between C10, N1 and N2 atoms range within 112.86 (7)–124.64 (7)°. The aluminium atom is only slightly displaced [0.1937 (9) Å] from the plane of these ligands towards the coordinated tetrahedral donor atom N3. The N3 and F18 atoms lie in the apical positions with an N3—Al1—F18 angle equal to 152.24 (5)°. As expected, the dative N3→Al1 bond length [2.0104 (13) Å] is significantly longer than equatorial nitrogen-aluminium distances [1.8575 (14) and 1.8697 (14) Å].