Literature DB >> 23284360

6-Benzyl-2-methyl-1,3-bis-(penta-fluoro-phen-yl)-1,3,6,2-triaza-alumocane.

Marina M Kireenko1, Kirill V Zaitsev, Andrei V Churakov, Galina S Zaitseva, Sergey S Karlov.   

Abstract

In the title compound, [Al(CH(3))(C(23)H(15)F(10)N(3))], the Al(III) atom is coordinated in a distorted tetra-hedral geometry by three N atoms from the tridentate amine and by one C atom of the methyl substituent. Further, there is a short intra-molecular Al⋯F contact [2.5717 (11) Å], leading to an overall distorted trigonal-bipyramidal coordination environment around Al(III).

Entities:  

Year:  2012        PMID： 23284360      PMCID： PMC3515133          DOI： 10.1107/S1600536812042560

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


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

[Al(CH3)(C23H15F10N3)] M = 565.39 Monoclinic, a = 7.9530 (14) Å b = 33.577 (6) Å c = 8.7247 (15) Å β = 100.809 (2)° V = 2288.5 (7) Å3 Z = 4 Mo Kα radiation μ = 0.19 mm−1 T = 173 K 0.20 × 0.20 × 0.05 mm

Data collection

Bruker SMART APEXII diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.963, T max = 0.991 19211 measured reflections 4972 independent reflections 4317 reflections with I > 2σ(I) R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.036 wR(F 2) = 0.094 S = 1.02 4972 reflections 415 parameters All H-atom parameters refined Δρmax = 0.36 e Å−3 Δρmin = −0.26 e Å−3 Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: 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. Click here for additional data file. Crystal structure: contains datablock(s) global. DOI: 10.1107/S1600536812042560/is5205sup1.cif Additional supplementary materials: crystallographic information; 3D view; checkCIF report
[Al(CH3)(C23H15F10N3)]F(000) = 1144
Mr = 565.39Dx = 1.641 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 8521 reflections
a = 7.9530 (14) Åθ = 2.5–28.1°
b = 33.577 (6) ŵ = 0.19 mm−1
c = 8.7247 (15) ÅT = 173 K
β = 100.809 (2)°Plate, colourless
V = 2288.5 (7) Å30.20 × 0.20 × 0.05 mm
Z = 4
Bruker SMART APEXII diffractometer4972 independent reflections
Radiation source: fine-focus sealed tube4317 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.021
ω scansθmax = 27.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2008)h = −10→10
Tmin = 0.963, Tmax = 0.991k = −42→42
19211 measured reflectionsl = −11→11
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036Hydrogen site location: difference Fourier map
wR(F2) = 0.094All H-atom parameters refined
S = 1.02w = 1/[σ2(Fo2) + (0.0439P)2 + 1.3304P] where P = (Fo2 + 2Fc2)/3
4972 reflections(Δ/σ)max < 0.001
415 parametersΔρmax = 0.36 e Å−3
0 restraintsΔρmin = −0.26 e Å−3
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.
xyzUiso*/Ueq
Al10.55982 (6)0.117782 (13)0.49859 (5)0.02089 (11)
N10.60780 (16)0.16461 (4)0.39907 (14)0.0223 (3)
N20.68539 (17)0.07207 (4)0.47836 (15)0.0254 (3)
N30.74288 (16)0.13396 (4)0.67940 (14)0.0214 (3)
C10.6675 (2)0.15076 (5)0.81197 (18)0.0247 (3)
C20.7938 (2)0.16032 (5)0.95983 (18)0.0267 (3)
C30.8602 (2)0.19843 (5)0.9886 (2)0.0308 (4)
C40.9723 (2)0.20708 (6)1.1272 (2)0.0375 (4)
C51.0209 (2)0.17743 (7)1.2368 (2)0.0408 (5)
C60.9549 (3)0.13976 (7)1.2102 (2)0.0407 (5)
C70.8404 (2)0.13109 (6)1.0735 (2)0.0340 (4)
C100.3337 (2)0.11830 (6)0.5555 (2)0.0304 (4)
C110.84769 (19)0.16404 (5)0.61234 (18)0.0236 (3)
C120.7313 (2)0.19083 (5)0.49746 (18)0.0232 (3)
C130.51390 (18)0.17824 (5)0.26115 (17)0.0212 (3)
C140.4895 (2)0.21746 (5)0.20674 (18)0.0235 (3)
C150.3887 (2)0.22716 (5)0.06498 (19)0.0261 (3)
C160.3087 (2)0.19796 (5)−0.03367 (18)0.0279 (3)
C170.3261 (2)0.15883 (5)0.01513 (18)0.0257 (3)
C180.4249 (2)0.15007 (5)0.15781 (18)0.0235 (3)
C210.8424 (2)0.09669 (5)0.72549 (19)0.0258 (3)
C220.8566 (2)0.07283 (5)0.58014 (19)0.0270 (3)
C230.6498 (2)0.04053 (5)0.37471 (18)0.0274 (3)
C240.7699 (2)0.01889 (5)0.3099 (2)0.0338 (4)
C250.7253 (3)−0.01322 (6)0.2104 (2)0.0405 (5)
C260.5577 (3)−0.02420 (5)0.1651 (2)0.0408 (5)
C270.4342 (3)−0.00290 (5)0.2209 (2)0.0371 (4)
C280.4803 (2)0.02780 (5)0.3244 (2)0.0304 (4)
F140.56225 (13)0.24841 (3)0.29513 (11)0.0310 (2)
F150.36334 (13)0.26570 (3)0.02492 (12)0.0354 (2)
F160.21053 (13)0.20771 (3)−0.17192 (11)0.0392 (3)
F170.24581 (13)0.12973 (3)−0.07535 (12)0.0371 (2)
F180.43879 (13)0.11143 (3)0.20488 (11)0.0309 (2)
F240.93701 (14)0.02933 (4)0.34006 (13)0.0452 (3)
F250.84828 (18)−0.03270 (4)0.15369 (15)0.0569 (4)
F260.51315 (19)−0.05520 (3)0.06690 (14)0.0553 (4)
F270.26773 (16)−0.01208 (3)0.17435 (14)0.0492 (3)
F280.35477 (13)0.04643 (3)0.37978 (13)0.0382 (3)
H1120.917 (2)0.1790 (5)0.6947 (19)0.018 (4)*
H1220.803 (2)0.2058 (5)0.436 (2)0.020 (4)*
H1210.675 (2)0.2111 (5)0.554 (2)0.020 (4)*
H2220.894 (2)0.0457 (6)0.615 (2)0.027 (5)*
H30.833 (2)0.2184 (5)0.912 (2)0.025 (4)*
H120.605 (2)0.1750 (6)0.774 (2)0.030 (5)*
H1110.921 (2)0.1507 (5)0.558 (2)0.024 (4)*
H2120.778 (2)0.0818 (5)0.790 (2)0.028 (5)*
H2210.950 (2)0.0841 (6)0.530 (2)0.028 (5)*
H110.585 (2)0.1307 (6)0.834 (2)0.031 (5)*
H2110.955 (2)0.1031 (6)0.787 (2)0.029 (5)*
H70.792 (2)0.1051 (6)1.055 (2)0.031 (5)*
H1030.310 (3)0.1447 (7)0.596 (3)0.050 (6)*
H41.012 (3)0.2322 (7)1.140 (2)0.036 (5)*
H51.097 (3)0.1834 (6)1.326 (3)0.045 (6)*
H1020.322 (3)0.0973 (7)0.630 (3)0.048 (6)*
H60.982 (3)0.1182 (7)1.285 (3)0.060 (7)*
H1010.255 (3)0.1136 (8)0.465 (3)0.064 (7)*
U11U22U33U12U13U23
Al10.0208 (2)0.0198 (2)0.0209 (2)0.00011 (17)0.00084 (17)0.00025 (17)
N10.0248 (6)0.0209 (6)0.0193 (6)−0.0020 (5)−0.0004 (5)0.0001 (5)
N20.0265 (7)0.0217 (6)0.0254 (7)0.0034 (5)−0.0016 (5)−0.0024 (5)
N30.0222 (6)0.0213 (6)0.0201 (6)0.0019 (5)0.0022 (5)−0.0006 (5)
C10.0233 (7)0.0286 (8)0.0216 (7)0.0019 (6)0.0028 (6)−0.0012 (6)
C20.0231 (7)0.0362 (9)0.0208 (7)0.0034 (6)0.0042 (6)−0.0041 (6)
C30.0287 (8)0.0338 (9)0.0293 (8)0.0055 (7)0.0038 (7)−0.0060 (7)
C40.0307 (9)0.0450 (11)0.0368 (10)−0.0016 (8)0.0066 (7)−0.0164 (8)
C50.0278 (9)0.0717 (14)0.0219 (8)0.0035 (9)0.0016 (7)−0.0107 (9)
C60.0403 (10)0.0600 (13)0.0212 (8)0.0057 (9)0.0042 (7)0.0045 (8)
C70.0361 (9)0.0418 (10)0.0242 (8)0.0004 (8)0.0059 (7)0.0013 (7)
C100.0238 (8)0.0363 (10)0.0303 (9)0.0002 (7)0.0031 (7)0.0010 (8)
C110.0217 (7)0.0258 (8)0.0223 (7)−0.0029 (6)0.0020 (6)−0.0018 (6)
C120.0238 (7)0.0222 (7)0.0230 (7)−0.0033 (6)0.0024 (6)−0.0022 (6)
C130.0200 (7)0.0241 (7)0.0201 (7)0.0002 (6)0.0051 (5)0.0007 (6)
C140.0241 (7)0.0227 (7)0.0237 (7)−0.0022 (6)0.0049 (6)−0.0006 (6)
C150.0261 (8)0.0254 (8)0.0273 (8)0.0012 (6)0.0065 (6)0.0075 (6)
C160.0229 (7)0.0391 (9)0.0205 (7)0.0007 (7)0.0007 (6)0.0063 (7)
C170.0232 (7)0.0313 (8)0.0223 (7)−0.0039 (6)0.0034 (6)−0.0045 (6)
C180.0250 (7)0.0221 (7)0.0236 (7)0.0008 (6)0.0054 (6)−0.0003 (6)
C210.0262 (8)0.0249 (8)0.0237 (8)0.0044 (6)−0.0018 (6)0.0008 (6)
C220.0256 (8)0.0256 (8)0.0274 (8)0.0059 (6)−0.0017 (6)−0.0017 (6)
C230.0370 (9)0.0188 (7)0.0238 (8)0.0026 (6)−0.0005 (6)0.0020 (6)
C240.0374 (9)0.0299 (9)0.0310 (9)0.0079 (7)−0.0020 (7)−0.0021 (7)
C250.0567 (12)0.0293 (9)0.0326 (9)0.0163 (8)0.0013 (8)−0.0025 (7)
C260.0650 (13)0.0200 (8)0.0313 (9)0.0015 (8)−0.0064 (9)−0.0029 (7)
C270.0492 (11)0.0227 (8)0.0343 (9)−0.0062 (8)−0.0050 (8)0.0036 (7)
C280.0389 (9)0.0200 (8)0.0302 (8)−0.0011 (7)0.0008 (7)0.0029 (6)
F140.0387 (5)0.0212 (5)0.0299 (5)−0.0042 (4)−0.0014 (4)0.0004 (4)
F150.0387 (6)0.0295 (5)0.0362 (5)0.0026 (4)0.0024 (4)0.0130 (4)
F160.0365 (6)0.0502 (7)0.0257 (5)−0.0025 (5)−0.0074 (4)0.0107 (5)
F170.0392 (6)0.0393 (6)0.0286 (5)−0.0072 (4)−0.0045 (4)−0.0082 (4)
F180.0384 (5)0.0214 (5)0.0300 (5)−0.0022 (4)−0.0009 (4)−0.0010 (4)
F240.0363 (6)0.0525 (7)0.0453 (6)0.0106 (5)0.0041 (5)−0.0165 (5)
F250.0693 (8)0.0504 (7)0.0465 (7)0.0275 (6)−0.0010 (6)−0.0186 (6)
F260.0880 (10)0.0271 (6)0.0431 (7)0.0011 (6)−0.0074 (6)−0.0131 (5)
F270.0533 (7)0.0347 (6)0.0531 (7)−0.0174 (5)−0.0067 (6)−0.0040 (5)
F280.0328 (5)0.0360 (6)0.0452 (6)−0.0056 (4)0.0054 (5)−0.0057 (5)
Al1—N21.8575 (14)C11—H1110.931 (19)
Al1—N11.8697 (14)C12—H1220.990 (17)
Al1—C101.9536 (18)C12—H1210.995 (17)
Al1—N32.0104 (13)C13—C141.401 (2)
Al1—F182.5717 (11)C13—C181.403 (2)
N1—C131.3704 (19)C14—F141.3573 (17)
N1—C121.4700 (19)C14—C151.381 (2)
N2—C231.387 (2)C15—F151.3457 (18)
N2—C221.480 (2)C15—C161.379 (2)
N3—C211.4947 (19)C16—F161.3486 (18)
N3—C111.497 (2)C16—C171.380 (2)
N3—C11.5086 (19)C17—F171.3404 (18)
C1—C21.514 (2)C17—C181.373 (2)
C1—H120.976 (19)C18—F181.3591 (18)
C1—H110.99 (2)C21—C221.522 (2)
C2—C31.389 (2)C21—H2120.972 (19)
C2—C71.395 (2)C21—H2110.980 (19)
C3—C41.392 (2)C22—H2220.987 (19)
C3—H30.946 (19)C22—H2211.004 (19)
C4—C51.384 (3)C23—C241.401 (2)
C4—H40.90 (2)C23—C281.404 (2)
C5—C61.372 (3)C24—F241.352 (2)
C5—H50.91 (2)C24—C251.388 (3)
C6—C71.390 (3)C25—F251.345 (2)
C6—H60.97 (3)C25—C261.368 (3)
C7—H70.96 (2)C26—F261.353 (2)
C10—H1030.98 (2)C26—C271.375 (3)
C10—H1020.98 (2)C27—F271.346 (2)
C10—H1010.92 (3)C27—C281.374 (2)
C11—C121.524 (2)C28—F281.342 (2)
C11—H1120.963 (17)
N2—Al1—N1119.38 (6)H112—C11—H111107.5 (14)
N2—Al1—C10124.64 (7)N1—C12—C11106.70 (12)
N1—Al1—C10112.86 (7)N1—C12—H122112.0 (10)
N2—Al1—N388.55 (6)C11—C12—H122108.6 (10)
N1—Al1—N387.50 (6)N1—C12—H121112.8 (10)
C10—Al1—N3111.33 (7)C11—C12—H121110.5 (10)
N2—Al1—F1886.80 (5)H122—C12—H121106.2 (14)
N1—Al1—F1871.20 (4)N1—C13—C14129.02 (14)
C10—Al1—F1893.65 (6)N1—C13—C18117.72 (14)
N3—Al1—F18152.24 (5)C14—C13—C18113.25 (13)
C13—N1—C12120.47 (12)F14—C14—C15116.26 (14)
C13—N1—Al1124.31 (10)F14—C14—C13120.67 (13)
C12—N1—Al1113.87 (9)C15—C14—C13123.05 (14)
C23—N2—C22117.19 (13)F15—C15—C16119.51 (14)
C23—N2—Al1130.18 (11)F15—C15—C14119.53 (14)
C22—N2—Al1112.29 (10)C16—C15—C14120.92 (15)
C21—N3—C11111.39 (12)F16—C16—C15120.50 (15)
C21—N3—C1111.92 (12)F16—C16—C17120.99 (15)
C11—N3—C1112.20 (12)C15—C16—C17118.46 (14)
C21—N3—Al1104.70 (9)F17—C17—C18120.41 (15)
C11—N3—Al1104.48 (9)F17—C17—C16120.21 (14)
C1—N3—Al1111.67 (9)C18—C17—C16119.37 (14)
N3—C1—C2115.91 (12)F18—C18—C17118.59 (13)
N3—C1—H12107.5 (11)F18—C18—C13116.52 (13)
C2—C1—H12109.0 (11)C17—C18—C13124.89 (15)
N3—C1—H11105.8 (11)N3—C21—C22109.57 (12)
C2—C1—H11109.8 (11)N3—C21—H212106.1 (11)
H12—C1—H11108.7 (15)C22—C21—H212110.1 (11)
C3—C2—C7118.60 (15)N3—C21—H211110.3 (11)
C3—C2—C1121.23 (15)C22—C21—H211111.8 (11)
C7—C2—C1120.12 (16)H212—C21—H211108.7 (15)
C2—C3—C4120.60 (18)N2—C22—C21107.78 (13)
C2—C3—H3119.8 (11)N2—C22—H222111.0 (10)
C4—C3—H3119.5 (11)C21—C22—H222107.3 (11)
C5—C4—C3120.01 (19)N2—C22—H221114.4 (10)
C5—C4—H4122.9 (13)C21—C22—H221110.1 (11)
C3—C4—H4117.1 (13)H222—C22—H221106.0 (15)
C6—C5—C4119.88 (17)N2—C23—C24126.01 (16)
C6—C5—H5121.3 (14)N2—C23—C28120.22 (15)
C4—C5—H5118.9 (14)C24—C23—C28113.77 (15)
C5—C6—C7120.41 (19)F24—C24—C25116.72 (16)
C5—C6—H6123.0 (15)F24—C24—C23120.44 (15)
C7—C6—H6116.6 (15)C25—C24—C23122.82 (17)
C6—C7—C2120.45 (19)F25—C25—C26119.94 (17)
C6—C7—H7121.0 (12)F25—C25—C24119.32 (19)
C2—C7—H7118.6 (12)C26—C25—C24120.70 (18)
Al1—C10—H103109.9 (13)F26—C26—C25121.03 (19)
Al1—C10—H102111.6 (13)F26—C26—C27120.31 (18)
H103—C10—H102111.6 (19)C25—C26—C27118.66 (16)
Al1—C10—H101106.8 (16)F27—C27—C28119.72 (18)
H103—C10—H101108 (2)F27—C27—C26120.11 (16)
H102—C10—H101108 (2)C28—C27—C26120.17 (18)
N3—C11—C12109.96 (12)F28—C28—C27117.51 (16)
N3—C11—H112110.2 (10)F28—C28—C23118.72 (14)
C12—C11—H112112.0 (10)C27—C28—C23123.77 (17)
N3—C11—H111108.8 (11)C18—F18—Al1102.48 (8)
C12—C11—H111108.3 (11)
  4 in total

1.  The Cambridge Structural Database: a quarter of a million crystal structures and rising.

Authors:  Frank H Allen
Journal:  Acta Crystallogr B       Date:  2002-05-29

2.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

3.  A new weakly coordinating aluminate anion incorporating a chelating perfluoro-bis-anilido ligand.

Authors:  Joshua C Smith; Kuangbiao Ma; Warren E Piers; Masood Parvez; Robert McDonald
Journal:  Dalton Trans       Date:  2010-09-14       Impact factor: 4.390

4.  Novel derivatives of hypervalent germanium: synthesis, structure, and stability.

Authors:  El'mira Kh Lermontova; Mengmeng Huan; Andrei V Churakov; Judith A K Howard; Maxim V Zabalov; Sergey S Karlov; Galina S Zaitseva
Journal:  Dalton Trans       Date:  2009-05-06       Impact factor: 4.390
  4 in total
  1 in total

1.  Crystal structure of a mixed-valence μ-oxide Sn12 cluster.

Authors:  Marina M Kireenko; Kirill V Zaitsev; Sergey S Karlov; Mikhail P Egorov; Andrei V Churakov
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2014-10-29
  1 in total

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