Bis[μ-2-(2H-benzotriazol-2-yl)-4-methyl-phenolato]bis-[dimethyl-aluminium(III)].

The title complex, [Al(2)(CH(3))(4)(C(13)H(10)N(3)O)(2)], is dimeric, bridged through the O atoms of the phenolate anions. The asymmetric unit contains one half of the mol-ecule and there is a crystallographic inversion centre in this mol-ecule. Each Al atom is penta-coordinated by one N atom and two bridging O atoms of two N,O-bidentate benzotriazolylphenolate ligands and by two C atoms from two methyl groups, forming a distorted trigonal-bipyramidal environment.

Related literature

For background information, see: Liu et al. (2001 ▶); Wu et n class="Chemical">al. (2006 ▶). For related structures, see: Lewinski et al. (2003 ▶); Tsai et al. (2009 ▶).

Experimental

Crystal data

[Al2(CH3)4(C13n class="Species">H10N3O)2]

M = 562.58

Triclinic,

a = 7.4220 (4) Å

b = 9.7120 (5) Å

c = 11.6331 (6) Å

α = 112.517 (2)°

β = 94.824 (3)°

γ = 109.574 (2)°

V = 707.79 (7) Å3

Z = 1

Mo Kα radiation

μ = 0.14 mm−1

T = 296 K

0.48 × 0.25 × 0.25 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.937, T max = 0.966

11757 measured reflections

3405 independent reflections

2923 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.122

S = 1.03

3405 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAIn class="Chemical">NT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, globn class="Chemical">al. DOI: 10.1107/S1600536809018492/rk2147sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809018492/rk2147Isup2.hkl

Additional supplementary materin class="Chemical">als: crystallographic information; 3D view; checkCIF report

[Al2(CH3)4(C13H10N3O)2]	Z = 1
Mr = 562.58	F(000) = 296
Triclinic, P1	Dx = 1.320 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4220 (4) Å	Cell parameters from 7401 reflections
b = 9.7120 (5) Å	θ = 2.5–28.2°
c = 11.6331 (6) Å	µ = 0.14 mm−1
α = 112.517 (2)°	T = 296 K
β = 94.824 (3)°	Block, yellow
γ = 109.574 (2)°	0.48 × 0.25 × 0.25 mm
V = 707.79 (7) Å3

Bruker APEXII CCD diffractometer	3405 independent reflections
Radiation source: fine-focus sealed tube	2923 reflections with I > 2σ(I)
graphite	Rint = 0.017
φ and ω scans	θmax = 28.2°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −9→8
Tmin = 0.937, Tmax = 0.966	k = −12→12
11757 measured reflections	l = −14→15

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0679P)2 + 0.1915P] where P = (Fo2 + 2Fc2)/3
3405 reflections	(Δ/σ)max = 0.001
182 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
Al	0.05537 (5)	0.05266 (4)	0.89433 (3)	0.03495 (10)
O	0.05448 (13)	0.14683 (10)	1.06417 (8)	0.0383 (2)
N1	0.16914 (16)	0.28879 (13)	0.90600 (11)	0.0394 (2)
N2	0.20710 (15)	0.42899 (12)	1.00733 (10)	0.0366 (2)
N3	0.28396 (18)	0.56192 (13)	0.98973 (12)	0.0457 (3)
C1	0.10477 (17)	0.30216 (14)	1.15315 (12)	0.0347 (3)
C2	0.17660 (18)	0.44012 (14)	1.12950 (12)	0.0348 (3)
C3	0.2281 (2)	0.59650 (15)	1.22664 (13)	0.0420 (3)
H3B	0.2737	0.6849	1.2076	0.050*
C4	0.2129 (2)	0.62320 (16)	1.35011 (13)	0.0435 (3)
C5	0.1424 (2)	0.48768 (17)	1.37431 (13)	0.0432 (3)
H5A	0.1312	0.5018	1.4567	0.052*
C6	0.0886 (2)	0.33235 (16)	1.27846 (13)	0.0421 (3)
H6A	0.0399	0.2447	1.2982	0.051*
C7	0.22611 (19)	0.33415 (16)	0.81377 (13)	0.0409 (3)
C8	0.2240 (2)	0.2418 (2)	0.68526 (15)	0.0546 (4)
H8A	0.1766	0.1290	0.6486	0.065*
C9	0.2959 (2)	0.3281 (2)	0.61786 (16)	0.0588 (4)
H9A	0.2961	0.2715	0.5328	0.071*
C10	0.3694 (2)	0.4988 (2)	0.67200 (16)	0.0566 (4)
H10A	0.4178	0.5511	0.6219	0.068*
C11	0.3719 (2)	0.5895 (2)	0.79461 (16)	0.0534 (4)
H11A	0.4203	0.7023	0.8297	0.064*
C12	0.29715 (19)	0.50377 (16)	0.86672 (14)	0.0416 (3)
C13	0.2747 (3)	0.7923 (2)	1.45629 (17)	0.0637 (5)
H13A	0.3229	0.8706	1.4231	0.096*
H13B	0.3771	0.8112	1.5237	0.096*
H13C	0.1635	0.8026	1.4896	0.096*
C14	−0.1914 (2)	−0.00914 (18)	0.77213 (15)	0.0490 (3)
H14A	−0.2766	−0.1197	0.7492	0.073*
H14B	−0.1613	0.0013	0.6964	0.073*
H14C	−0.2562	0.0610	0.8114	0.073*
C15	0.2981 (2)	0.02143 (18)	0.86005 (16)	0.0501 (3)
H15A	0.2845	−0.0846	0.8501	0.075*
H15B	0.4081	0.1025	0.9306	0.075*
H15C	0.3199	0.0312	0.7828	0.075*

	U11	U22	U33	U12	U13	U23
Al	0.03920 (19)	0.03075 (17)	0.03427 (18)	0.01356 (14)	0.01205 (14)	0.01332 (13)
O	0.0501 (5)	0.0270 (4)	0.0362 (4)	0.0132 (3)	0.0149 (4)	0.0131 (3)
N1	0.0451 (5)	0.0326 (5)	0.0389 (5)	0.0130 (4)	0.0134 (4)	0.0155 (4)
N2	0.0380 (5)	0.0293 (4)	0.0405 (5)	0.0110 (4)	0.0075 (4)	0.0160 (4)
N3	0.0533 (6)	0.0335 (5)	0.0504 (6)	0.0124 (5)	0.0101 (5)	0.0231 (5)
C1	0.0349 (5)	0.0294 (5)	0.0369 (6)	0.0121 (4)	0.0098 (4)	0.0122 (4)
C2	0.0354 (5)	0.0312 (5)	0.0362 (6)	0.0136 (4)	0.0064 (4)	0.0132 (4)
C3	0.0457 (7)	0.0305 (5)	0.0440 (7)	0.0144 (5)	0.0041 (5)	0.0128 (5)
C4	0.0436 (6)	0.0354 (6)	0.0414 (7)	0.0166 (5)	0.0031 (5)	0.0074 (5)
C5	0.0450 (7)	0.0433 (6)	0.0353 (6)	0.0178 (5)	0.0108 (5)	0.0110 (5)
C6	0.0473 (7)	0.0382 (6)	0.0403 (6)	0.0158 (5)	0.0156 (5)	0.0167 (5)
C7	0.0398 (6)	0.0427 (6)	0.0441 (6)	0.0150 (5)	0.0134 (5)	0.0234 (5)
C8	0.0635 (9)	0.0543 (8)	0.0464 (7)	0.0219 (7)	0.0219 (7)	0.0223 (6)
C9	0.0581 (8)	0.0775 (10)	0.0476 (8)	0.0259 (8)	0.0207 (6)	0.0338 (7)
C10	0.0463 (7)	0.0758 (9)	0.0619 (9)	0.0192 (7)	0.0156 (6)	0.0483 (7)
C11	0.0506 (8)	0.0551 (7)	0.0636 (9)	0.0157 (6)	0.0132 (6)	0.0395 (7)
C12	0.0382 (6)	0.0427 (6)	0.0481 (7)	0.0141 (5)	0.0086 (5)	0.0261 (5)
C13	0.0802 (11)	0.0409 (8)	0.0481 (9)	0.0224 (8)	0.0030 (8)	0.0019 (6)
C14	0.0484 (7)	0.0451 (7)	0.0506 (8)	0.0163 (6)	0.0066 (6)	0.0213 (6)
C15	0.0452 (7)	0.0443 (7)	0.0595 (8)	0.0189 (6)	0.0192 (6)	0.0192 (6)

Al—O	1.8337 (10)	C6—H6A	0.9300
Al—C15	1.9725 (15)	C7—C12	1.3991 (19)
Al—C14	1.9767 (15)	C7—C8	1.414 (2)
Al—Oi	2.0918 (10)	C8—C9	1.370 (2)
Al—N1	2.1060 (11)	C8—H8A	0.9300
O—C1	1.3595 (14)	C9—C10	1.407 (2)
O—Ali	2.0918 (10)	C9—H9A	0.9300
N1—N2	1.3344 (15)	C10—C11	1.354 (2)
N1—C7	1.3556 (18)	C10—H10A	0.9300
N2—N3	1.3277 (15)	C11—C12	1.417 (2)
N2—C2	1.4268 (17)	C11—H11A	0.9300
N3—C12	1.3483 (19)	C13—H13A	0.9600
C1—C6	1.3967 (18)	C13—H13B	0.9600
C1—C2	1.4084 (18)	C13—H13C	0.9600
C2—C3	1.3978 (17)	C14—H14A	0.9600
C3—C4	1.380 (2)	C14—H14B	0.9600
C3—H3B	0.9300	C14—H14C	0.9600
C4—C5	1.390 (2)	C15—H15A	0.9600
C4—C13	1.5098 (19)	C15—H15B	0.9600
C5—C6	1.3826 (18)	C15—H15C	0.9600
C5—H5A	0.9300
O—Al—C15	115.55 (6)	C1—C6—H6A	118.8
O—Al—C14	114.97 (6)	N1—C7—C12	107.66 (12)
C15—Al—C14	129.44 (7)	N1—C7—C8	131.38 (13)
O—Al—Oi	76.96 (4)	C12—C7—C8	120.97 (13)
C15—Al—Oi	94.55 (6)	C9—C8—C7	116.14 (15)
C14—Al—Oi	94.85 (5)	C9—C8—H8A	121.9
O—Al—N1	87.28 (4)	C7—C8—H8A	121.9
C15—Al—N1	92.11 (6)	C8—C9—C10	122.70 (16)
C14—Al—N1	91.89 (6)	C8—C9—H9A	118.7
Oi—Al—N1	164.24 (4)	C10—C9—H9A	118.7
C1—O—Al	134.46 (8)	C11—C10—C9	122.11 (15)
C1—O—Ali	122.50 (8)	C11—C10—H10A	118.9
Al—O—Ali	103.04 (4)	C9—C10—H10A	118.9
N2—N1—C7	103.95 (11)	C10—C11—C12	116.60 (15)
N2—N1—Al	127.89 (9)	C10—C11—H11A	121.7
C7—N1—Al	128.13 (9)	C12—C11—H11A	121.7
N3—N2—N1	115.67 (11)	N3—C12—C7	109.19 (12)
N3—N2—C2	120.79 (11)	N3—C12—C11	129.32 (13)
N1—N2—C2	123.49 (10)	C7—C12—C11	121.48 (14)
N2—N3—C12	103.53 (11)	C4—C13—H13A	109.5
O—C1—C6	119.56 (11)	C4—C13—H13B	109.5
O—C1—C2	124.65 (11)	H13A—C13—H13B	109.5
C6—C1—C2	115.79 (11)	C4—C13—H13C	109.5
C3—C2—C1	121.32 (12)	H13A—C13—H13C	109.5
C3—C2—N2	116.43 (11)	H13B—C13—H13C	109.5
C1—C2—N2	122.22 (11)	Al—C14—H14A	109.5
C4—C3—C2	121.75 (13)	Al—C14—H14B	109.5
C4—C3—H3B	119.1	H14A—C14—H14B	109.5
C2—C3—H3B	119.1	Al—C14—H14C	109.5
C3—C4—C5	117.29 (12)	H14A—C14—H14C	109.5
C3—C4—C13	121.89 (14)	H14B—C14—H14C	109.5
C5—C4—C13	120.80 (14)	Al—C15—H15A	109.5
C6—C5—C4	121.39 (13)	Al—C15—H15B	109.5
C6—C5—H5A	119.3	H15A—C15—H15B	109.5
C4—C5—H5A	119.3	Al—C15—H15C	109.5
C5—C6—C1	122.45 (13)	H15A—C15—H15C	109.5
C5—C6—H6A	118.8	H15B—C15—H15C	109.5