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The title dinuclear compound, bis[μ-6,6'-di-tert-butyl-4,4′-dimethyl-2,2-(ethylenedithio)diphenolato]bis[methylaluminium(I)], [Al2(CH3)2(C24H32O2S2)] or [AlMe(etbmp)]2 [where etbmpH2 is 6,6′-di-tert-butyl-4,4′-dimethyl-2,2- (ethylenedithio)diphenol], was obtained by reaction of trimethylaluminum with etbmpH2, as shown by X-ray diffraction of a single crystal. The molecule possesses a crystallographic twofold axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804033793/dn6188sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804033793/dn6188Isup2.hkl
Contains datablock I

CCDC reference: 248947

Key indicators

  • Single-crystal X-ray study
  • T = 110 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.041
  • wR factor = 0.109
  • Data-to-parameter ratio = 22.4

checkCIF/PLATON results

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Alert level C PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.09 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.83 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.39 Ratio
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (2001); cell refinement: SMART (2001); data reduction: SAINT-Plus (1999); program(s) used to solve structure: SHELXS86 (Sheldrick, 1986); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997).

bis[µ-6,6'-di-tert-butyl-4,4'-dimethyl-2,2- (ethylenedithio)diphenolato]bis[methylaluminium(I)] top
Crystal data top
[Al2(CH3)2(C24H32O2S2)]4F(000) = 1968
Mr = 917.33Dx = 1.210 Mg m3
Orthorhombic, PccnMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ab 2acCell parameters from 8096 reflections
a = 10.7048 (17) Åθ = 1.9–28.3°
b = 16.380 (3) ŵ = 0.27 mm1
c = 28.722 (5) ÅT = 110 K
V = 5036.2 (14) Å3Irregular, colourless
Z = 40.60 × 0.56 × 0.30 mm
Data collection top
Bruker SMART AXS
diffractometer with CCD area detector
6270 independent reflections
Radiation source: fine-focus sealed tube5520 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.033
ω–scansθmax = 28.3°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1414
Tmin = 0.857, Tmax = 0.925k = 2121
50262 measured reflectionsl = 3837
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109H-atom parameters not refined
S = 1.07 w = 1/[σ2(Fo2) + (0.0611P)2 + 2.2698P]
where P = (Fo2 + 2Fc2)/3
6270 reflections(Δ/σ)max = 0.001
280 parametersΔρmax = 0.50 e Å3
0 restraintsΔρmin = 0.24 e Å3
Special details top

Experimental. The values of Tmin and Tmax are 0.831245 and 1.000000 from SADABS.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Al0.46275 (4)0.35880 (3)0.137683 (15)0.01908 (11)
O10.41212 (9)0.33448 (6)0.19448 (3)0.0209 (2)
O20.41275 (9)0.32237 (6)0.08252 (3)0.0198 (2)
S10.58427 (3)0.22471 (2)0.147239 (12)0.02002 (9)
S20.25115 (3)0.43452 (2)0.130934 (11)0.01834 (9)
C10.48008 (13)0.29053 (8)0.22487 (5)0.0198 (3)
C20.56238 (13)0.23039 (8)0.20833 (5)0.0198 (3)
C30.62939 (14)0.17999 (8)0.23850 (5)0.0231 (3)
H30.68510.14010.22640.028*
C40.61436 (14)0.18830 (9)0.28589 (5)0.0258 (3)
C50.53686 (15)0.25080 (10)0.30215 (5)0.0270 (3)
H50.52890.25750.33490.032*
C60.47059 (14)0.30390 (9)0.27346 (5)0.0236 (3)
C70.68056 (17)0.13231 (11)0.31949 (6)0.0344 (4)
H7A0.61910.09810.33550.052*
H7B0.72640.16500.34240.052*
H7C0.73920.09750.30240.052*
C80.39515 (17)0.37582 (10)0.29311 (5)0.0309 (4)
C90.3996 (2)0.37875 (14)0.34647 (6)0.0518 (6)
H9A0.48680.38180.35680.078*
H9B0.36080.32940.35920.078*
H9C0.35410.42690.35750.078*
C100.4525 (2)0.45572 (11)0.27520 (7)0.0441 (5)
H10A0.53960.45950.28540.066*
H10B0.40520.50210.28760.066*
H10C0.44910.45660.24110.066*
C110.25754 (19)0.37165 (13)0.27857 (7)0.0434 (5)
H11A0.21190.41730.29260.065*
H11B0.22140.31990.28920.065*
H11C0.25140.37510.24460.065*
C120.48148 (13)0.14021 (8)0.13055 (5)0.0201 (3)
H12A0.48740.13180.09650.024*
H12B0.51080.08960.14590.024*
C130.35306 (13)0.37214 (8)0.05243 (5)0.0183 (3)
C140.26576 (13)0.42851 (8)0.06970 (5)0.0183 (3)
C150.19836 (13)0.48007 (8)0.04044 (5)0.0199 (3)
H150.14040.51800.05310.024*
C160.21635 (13)0.47573 (9)0.00732 (5)0.0214 (3)
C170.30564 (14)0.42115 (9)0.02419 (5)0.0215 (3)
H170.31900.41920.05690.026*
C180.37644 (13)0.36939 (8)0.00387 (5)0.0194 (3)
C190.14317 (15)0.52926 (10)0.04019 (5)0.0272 (3)
H19A0.07590.55660.02310.041*
H19B0.10730.49570.06500.041*
H19C0.19880.57030.05380.041*
C200.47719 (14)0.31349 (9)0.01654 (5)0.0232 (3)
C210.44543 (17)0.22378 (9)0.00741 (6)0.0326 (4)
H21A0.43770.21470.02620.049*
H21B0.51200.18900.01990.049*
H21C0.36630.21020.02270.049*
C220.60414 (15)0.33460 (11)0.00530 (6)0.0333 (4)
H22A0.62070.39300.00140.050*
H22B0.67000.30300.01010.050*
H22C0.60270.32120.03850.050*
C230.4907 (2)0.32461 (12)0.06914 (6)0.0399 (4)
H23A0.41100.31220.08440.060*
H23B0.55540.28760.08090.060*
H23C0.51450.38120.07590.060*
C240.15310 (13)0.34547 (8)0.14337 (5)0.0190 (3)
H24A0.18510.29790.12580.023*
H24B0.15860.33240.17700.023*
C250.59118 (16)0.44265 (10)0.13575 (6)0.0311 (3)
H25A0.67270.41800.14220.047*
H25B0.57300.48440.15920.047*
H25C0.59250.46780.10480.047*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Al0.0213 (2)0.0165 (2)0.0194 (2)0.00149 (15)0.00257 (15)0.00155 (15)
O10.0244 (5)0.0205 (5)0.0176 (5)0.0045 (4)0.0035 (4)0.0015 (4)
O20.0254 (5)0.0162 (4)0.0176 (4)0.0020 (4)0.0020 (4)0.0024 (4)
S10.01894 (17)0.01926 (17)0.02185 (17)0.00003 (12)0.00031 (12)0.00026 (12)
S20.02299 (18)0.01495 (17)0.01708 (17)0.00109 (12)0.00083 (12)0.00025 (11)
C10.0236 (7)0.0158 (6)0.0200 (7)0.0002 (5)0.0049 (5)0.0012 (5)
C20.0218 (6)0.0176 (6)0.0199 (6)0.0017 (5)0.0027 (5)0.0001 (5)
C30.0236 (7)0.0165 (6)0.0292 (7)0.0009 (5)0.0027 (6)0.0025 (5)
C40.0279 (7)0.0217 (7)0.0279 (7)0.0013 (6)0.0063 (6)0.0059 (6)
C50.0357 (8)0.0254 (7)0.0199 (7)0.0027 (6)0.0050 (6)0.0025 (6)
C60.0312 (8)0.0192 (6)0.0202 (7)0.0036 (6)0.0051 (5)0.0009 (5)
C70.0388 (9)0.0326 (9)0.0317 (8)0.0089 (7)0.0044 (7)0.0118 (7)
C80.0462 (10)0.0265 (8)0.0201 (7)0.0131 (7)0.0086 (6)0.0055 (6)
C90.0819 (16)0.0511 (12)0.0225 (8)0.0329 (11)0.0067 (9)0.0100 (8)
C100.0654 (13)0.0224 (8)0.0445 (11)0.0101 (8)0.0139 (9)0.0088 (7)
C110.0409 (10)0.0472 (11)0.0423 (10)0.0175 (9)0.0010 (8)0.0168 (8)
C120.0224 (7)0.0164 (6)0.0216 (7)0.0008 (5)0.0004 (5)0.0028 (5)
C130.0214 (6)0.0145 (6)0.0189 (6)0.0029 (5)0.0019 (5)0.0030 (5)
C140.0219 (6)0.0166 (6)0.0164 (6)0.0031 (5)0.0005 (5)0.0015 (5)
C150.0209 (6)0.0167 (6)0.0221 (7)0.0004 (5)0.0000 (5)0.0022 (5)
C160.0229 (7)0.0196 (6)0.0216 (7)0.0011 (5)0.0026 (5)0.0048 (5)
C170.0259 (7)0.0207 (6)0.0181 (6)0.0021 (5)0.0006 (5)0.0024 (5)
C180.0228 (7)0.0156 (6)0.0197 (6)0.0024 (5)0.0007 (5)0.0013 (5)
C190.0280 (7)0.0302 (8)0.0233 (7)0.0040 (6)0.0022 (6)0.0077 (6)
C200.0283 (7)0.0196 (7)0.0216 (7)0.0024 (6)0.0037 (5)0.0006 (5)
C210.0399 (9)0.0183 (7)0.0396 (9)0.0003 (6)0.0069 (7)0.0027 (6)
C220.0245 (8)0.0331 (8)0.0423 (9)0.0009 (6)0.0049 (7)0.0047 (7)
C230.0534 (11)0.0412 (10)0.0252 (8)0.0171 (8)0.0118 (8)0.0027 (7)
C240.0208 (6)0.0159 (6)0.0202 (6)0.0008 (5)0.0006 (5)0.0036 (5)
C250.0282 (8)0.0248 (8)0.0404 (9)0.0080 (6)0.0012 (7)0.0015 (6)
Geometric parameters (Å, º) top
Al—O11.7645 (11)C11—H11C0.9800
Al—O21.7755 (11)C12—C24i1.505 (2)
Al—C251.9441 (16)C12—H12A0.9900
Al—S12.5673 (6)C12—H12B0.9900
Al—S22.5897 (6)C13—C141.4042 (19)
O1—C11.3452 (16)C13—C181.4180 (19)
O2—C131.3490 (16)C14—C151.3928 (19)
S1—C21.7727 (15)C15—C161.3872 (19)
S1—C121.8320 (14)C15—H150.9500
S2—C141.7685 (14)C16—C171.395 (2)
S2—C241.8321 (14)C16—C191.5078 (19)
C1—C21.4044 (19)C17—C181.3937 (19)
C1—C61.416 (2)C17—H170.9500
C2—C31.3954 (19)C18—C201.531 (2)
C3—C41.377 (2)C19—H19A0.9800
C3—H30.9500C19—H19B0.9800
C4—C51.398 (2)C19—H19C0.9800
C4—C71.508 (2)C20—C231.529 (2)
C5—C61.392 (2)C20—C211.531 (2)
C5—H50.9500C20—C221.536 (2)
C6—C81.536 (2)C21—H21A0.9800
C7—H7A0.9800C21—H21B0.9800
C7—H7B0.9800C21—H21C0.9800
C7—H7C0.9800C22—H22A0.9800
C8—C111.533 (3)C22—H22B0.9800
C8—C101.534 (3)C22—H22C0.9800
C8—C91.534 (2)C23—H23A0.9800
C9—H9A0.9800C23—H23B0.9800
C9—H9B0.9800C23—H23C0.9800
C9—H9C0.9800C24—C12i1.505 (2)
C10—H10A0.9800C24—H24A0.9900
C10—H10B0.9800C24—H24B0.9900
C10—H10C0.9800C25—H25A0.9800
C11—H11A0.9800C25—H25B0.9800
C11—H11B0.9800C25—H25C0.9800
O1—Al—O2131.03 (5)C24i—C12—S1113.14 (9)
O1—Al—C25113.77 (7)C24i—C12—H12A109.0
O2—Al—C25115.16 (7)S1—C12—H12A109.0
O1—Al—S182.16 (4)C24i—C12—H12B109.0
O2—Al—S187.74 (4)S1—C12—H12B109.0
C25—Al—S1104.42 (6)H12A—C12—H12B107.8
O1—Al—S284.76 (4)O2—C13—C14119.10 (12)
O2—Al—S280.24 (4)O2—C13—C18121.83 (12)
C25—Al—S2106.15 (6)C14—C13—C18119.06 (12)
S1—Al—S2149.42 (2)C15—C14—C13122.03 (12)
C1—O1—Al123.69 (9)C15—C14—S2121.36 (11)
C13—O2—Al120.75 (9)C13—C14—S2116.53 (10)
C2—S1—C12102.67 (6)C16—C15—C14119.58 (13)
C2—S1—Al89.66 (5)C16—C15—H15120.2
C12—S1—Al108.30 (5)C14—C15—H15120.2
C14—S2—C24101.56 (6)C15—C16—C17118.11 (13)
C14—S2—Al88.31 (5)C15—C16—C19121.15 (13)
C24—S2—Al96.04 (5)C17—C16—C19120.74 (13)
O1—C1—C2119.67 (12)C18—C17—C16124.16 (13)
O1—C1—C6121.19 (12)C18—C17—H17117.9
C2—C1—C6119.13 (12)C16—C17—H17117.9
C3—C2—C1121.83 (13)C17—C18—C13116.96 (13)
C3—C2—S1121.05 (11)C17—C18—C20121.70 (12)
C1—C2—S1117.04 (10)C13—C18—C20121.32 (12)
C4—C3—C2119.68 (14)C16—C19—H19A109.5
C4—C3—H3120.2C16—C19—H19B109.5
C2—C3—H3120.2H19A—C19—H19B109.5
C3—C4—C5118.15 (13)C16—C19—H19C109.5
C3—C4—C7121.16 (14)H19A—C19—H19C109.5
C5—C4—C7120.69 (14)H19B—C19—H19C109.5
C6—C5—C4124.21 (14)C23—C20—C21107.74 (13)
C6—C5—H5117.9C23—C20—C18111.95 (12)
C4—C5—H5117.9C21—C20—C18110.61 (12)
C5—C6—C1116.74 (13)C23—C20—C22107.03 (14)
C5—C6—C8121.99 (13)C21—C20—C22110.04 (13)
C1—C6—C8121.22 (13)C18—C20—C22109.40 (12)
C4—C7—H7A109.5C20—C21—H21A109.5
C4—C7—H7B109.5C20—C21—H21B109.5
H7A—C7—H7B109.5H21A—C21—H21B109.5
C4—C7—H7C109.5C20—C21—H21C109.5
H7A—C7—H7C109.5H21A—C21—H21C109.5
H7B—C7—H7C109.5H21B—C21—H21C109.5
C11—C8—C10109.33 (15)C20—C22—H22A109.5
C11—C8—C9107.68 (16)C20—C22—H22B109.5
C10—C8—C9107.20 (16)H22A—C22—H22B109.5
C11—C8—C6111.79 (13)C20—C22—H22C109.5
C10—C8—C6108.72 (15)H22A—C22—H22C109.5
C9—C8—C6112.00 (13)H22B—C22—H22C109.5
C8—C9—H9A109.5C20—C23—H23A109.5
C8—C9—H9B109.5C20—C23—H23B109.5
H9A—C9—H9B109.5H23A—C23—H23B109.5
C8—C9—H9C109.5C20—C23—H23C109.5
H9A—C9—H9C109.5H23A—C23—H23C109.5
H9B—C9—H9C109.5H23B—C23—H23C109.5
C8—C10—H10A109.5C12i—C24—S2112.12 (9)
C8—C10—H10B109.5C12i—C24—H24A109.2
H10A—C10—H10B109.5S2—C24—H24A109.2
C8—C10—H10C109.5C12i—C24—H24B109.2
H10A—C10—H10C109.5S2—C24—H24B109.2
H10B—C10—H10C109.5H24A—C24—H24B107.9
C8—C11—H11A109.5Al—C25—H25A109.5
C8—C11—H11B109.5Al—C25—H25B109.5
H11A—C11—H11B109.5H25A—C25—H25B109.5
C8—C11—H11C109.5Al—C25—H25C109.5
H11A—C11—H11C109.5H25A—C25—H25C109.5
H11B—C11—H11C109.5H25B—C25—H25C109.5
O2—Al—O1—C1108.40 (11)O1—C1—C6—C5174.81 (13)
C25—Al—O1—C174.03 (12)C2—C1—C6—C55.4 (2)
S1—Al—O1—C128.33 (10)O1—C1—C6—C87.7 (2)
S2—Al—O1—C1179.38 (10)C2—C1—C6—C8172.12 (14)
O1—Al—O2—C13112.45 (10)C5—C6—C8—C11122.78 (17)
C25—Al—O2—C1365.09 (12)C1—C6—C8—C1159.8 (2)
S1—Al—O2—C13169.97 (10)C5—C6—C8—C10116.43 (17)
S2—Al—O2—C1338.27 (9)C1—C6—C8—C1060.94 (19)
O1—Al—S1—C217.52 (6)C5—C6—C8—C91.8 (2)
O2—Al—S1—C2149.48 (6)C1—C6—C8—C9179.21 (17)
C25—Al—S1—C295.10 (7)C2—S1—C12—C24i58.93 (11)
S2—Al—S1—C283.06 (6)Al—S1—C12—C24i34.97 (11)
O1—Al—S1—C1285.72 (6)Al—O2—C13—C1438.93 (16)
O2—Al—S1—C1246.24 (6)Al—O2—C13—C18140.77 (11)
C25—Al—S1—C12161.66 (7)O2—C13—C14—C15178.17 (12)
S2—Al—S1—C1220.18 (7)C18—C13—C14—C152.1 (2)
O1—Al—S2—C14159.34 (6)O2—C13—C14—S24.92 (17)
O2—Al—S2—C1426.13 (5)C18—C13—C14—S2174.78 (10)
C25—Al—S2—C1487.41 (7)C24—S2—C14—C15103.78 (12)
S1—Al—S2—C1494.44 (6)Al—S2—C14—C15160.40 (11)
O1—Al—S2—C2457.89 (6)C24—S2—C14—C1379.29 (11)
O2—Al—S2—C2475.32 (6)Al—S2—C14—C1316.53 (10)
C25—Al—S2—C24171.15 (7)C13—C14—C15—C160.6 (2)
S1—Al—S2—C247.00 (6)S2—C14—C15—C16177.32 (11)
Al—O1—C1—C230.70 (17)C14—C15—C16—C172.2 (2)
Al—O1—C1—C6149.11 (11)C14—C15—C16—C19178.69 (13)
O1—C1—C2—C3176.18 (13)C15—C16—C17—C181.3 (2)
C6—C1—C2—C34.0 (2)C19—C16—C17—C18179.61 (14)
O1—C1—C2—S17.16 (18)C16—C17—C18—C131.3 (2)
C6—C1—C2—S1172.65 (11)C16—C17—C18—C20177.25 (13)
C12—S1—C2—C383.90 (13)O2—C13—C18—C17177.34 (12)
Al—S1—C2—C3167.41 (11)C14—C13—C18—C172.96 (19)
C12—S1—C2—C199.41 (12)O2—C13—C18—C204.1 (2)
Al—S1—C2—C19.29 (11)C14—C13—C18—C20175.61 (12)
C1—C2—C3—C40.6 (2)C17—C18—C20—C231.9 (2)
S1—C2—C3—C4177.17 (11)C13—C18—C20—C23176.60 (14)
C2—C3—C4—C53.6 (2)C17—C18—C20—C21118.27 (15)
C2—C3—C4—C7177.09 (14)C13—C18—C20—C2163.23 (18)
C3—C4—C5—C62.0 (2)C17—C18—C20—C22120.37 (15)
C7—C4—C5—C6178.64 (16)C13—C18—C20—C2258.14 (17)
C4—C5—C6—C12.5 (2)C14—S2—C24—C12i75.62 (11)
C4—C5—C6—C8174.97 (16)Al—S2—C24—C12i165.12 (9)
Symmetry code: (i) x+1/2, y+1/2, z.
 

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