[1,1-(Butane-1,4-diyl)-2,3-dicyclohexylguanidinato]dimethylaluminum(III).

In the crystal structure of the title complex, [Al(CH(3))(2)(C(17)H(30)N(3))], the Al(III) cation is coordinated by two methyl ligands and two N atoms from the guanidinato ligand in a distorted tetra-hedral geometry. The dihedral angle between the CN(2) and AlC(2) planes is 85.37 (2)°. The two N atoms of the guanidinato ligand exhibit an almost uniform affinity to the metal atom.

Related literature

For related guanidinato compounds, see: Chandra et al. (1970 ▶); Coles & Hitchcock (2004 ▶); Corey et al. (2006 ▶); Zhou et al. (2007 ▶). For related ortho metalation reactions, see: Kondo et al. (2007 ▶).

Experimental

Crystal data

[Al(CH3)2(C17H30N3)]

M = 333.49

Orthorhombic,

a = 18.263 (4) Å

b = 10.596 (2) Å

c = 10.449 (2) Å

V = 2022.0 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 293 K

0.40 × 0.30 × 0.30 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.959, T max = 0.969

7156 measured reflections

1772 independent reflections

1630 reflections with I > 2σ(I)

R int = 0.059

Refinement

R[F 2 > 2σ(F 2)] = 0.095

wR(F 2) = 0.232

S = 1.42

1772 reflections

107 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.43 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810046787/jh2223sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810046787/jh2223Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Al(CH3)2(C17H30N3)]	Dx = 1.095 Mg m−3
Mr = 333.49	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbcn	Cell parameters from 4606 reflections
a = 18.263 (4) Å	θ = 3.0–27.0°
b = 10.596 (2) Å	µ = 0.11 mm−1
c = 10.449 (2) Å	T = 293 K
V = 2022.0 (7) Å3	Block, colorless
Z = 4	0.40 × 0.30 × 0.30 mm
F(000) = 736

Bruker SMART CCD area-detector diffractometer	1772 independent reflections
Radiation source: fine-focus sealed tube	1630 reflections with I > 2σ(I)
graphite	Rint = 0.059
phi and ω scans	θmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −21→21
Tmin = 0.959, Tmax = 0.969	k = −12→7
7156 measured reflections	l = −11→12

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)] = 0.095	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.232	H-atom parameters constrained
S = 1.42	w = 1/[σ2(Fo2) + (0.P)2 + 5.155P] where P = (Fo2 + 2Fc2)/3
1772 reflections	(Δ/σ)max = 0.005
107 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.43 e Å−3

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.

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 > 2sigma(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	0.5000	0.29276 (18)	0.2500	0.0381 (6)
N1	0.45266 (19)	0.1440 (3)	0.1850 (3)	0.0310 (8)
N3	0.5000	−0.0569 (5)	0.2500	0.0397 (13)
C1	0.5000	0.0706 (6)	0.2500	0.0318 (13)
C2	0.3760 (2)	0.1118 (4)	0.1598 (4)	0.0334 (10)
H2	0.3744	0.0415	0.0989	0.040*
C3	0.3350 (3)	0.0733 (5)	0.2815 (5)	0.0418 (12)
H3A	0.3575	−0.0019	0.3170	0.050*
H3B	0.3392	0.1402	0.3444	0.050*
C4	0.2546 (3)	0.0474 (5)	0.2557 (7)	0.0611 (15)
H4A	0.2302	0.0270	0.3355	0.073*
H4B	0.2501	−0.0247	0.1991	0.073*
C5	0.2177 (3)	0.1614 (6)	0.1948 (6)	0.0569 (15)
H5A	0.1673	0.1407	0.1743	0.068*
H5B	0.2175	0.2309	0.2551	0.068*
C6	0.2573 (3)	0.2010 (6)	0.0742 (5)	0.0539 (14)
H6A	0.2349	0.2770	0.0405	0.065*
H6B	0.2525	0.1352	0.0102	0.065*
C7	0.3384 (2)	0.2255 (5)	0.1001 (5)	0.0435 (12)
H7A	0.3626	0.2465	0.0203	0.052*
H7B	0.3432	0.2972	0.1571	0.052*
C14	0.4666 (3)	−0.1349 (4)	0.1484 (5)	0.0473 (13)
H14A	0.4815	−0.1066	0.0641	0.057*
H14B	0.4136	−0.1338	0.1538	0.057*
C15	0.4971 (3)	−0.2657 (5)	0.1782 (6)	0.0613 (16)
H15A	0.4642	−0.3314	0.1486	0.074*
H15B	0.5447	−0.2777	0.1388	0.074*
C18	0.4388 (3)	0.3932 (5)	0.3656 (6)	0.0586 (16)
H18A	0.4076	0.3382	0.4141	0.088*
H18B	0.4093	0.4505	0.3165	0.088*
H18C	0.4695	0.4403	0.4229	0.088*

	U11	U22	U33	U12	U13	U23
Al	0.0304 (10)	0.0312 (10)	0.0526 (12)	0.000	−0.0093 (9)	0.000
N1	0.0254 (17)	0.0324 (18)	0.0351 (19)	−0.0015 (15)	0.0006 (15)	0.0007 (16)
N3	0.037 (3)	0.033 (3)	0.049 (3)	0.000	0.007 (3)	0.000
C1	0.032 (3)	0.032 (3)	0.032 (3)	0.000	0.010 (3)	0.000
C2	0.029 (2)	0.037 (2)	0.034 (2)	−0.0060 (18)	0.0002 (18)	−0.0059 (19)
C3	0.036 (2)	0.043 (3)	0.047 (3)	0.004 (2)	0.006 (2)	0.009 (2)
C4	0.033 (2)	0.057 (3)	0.094 (4)	−0.005 (2)	0.011 (3)	0.020 (3)
C5	0.026 (2)	0.061 (3)	0.084 (4)	−0.002 (2)	−0.001 (3)	0.006 (3)
C6	0.037 (3)	0.070 (4)	0.055 (3)	0.001 (3)	−0.014 (2)	0.000 (3)
C7	0.032 (2)	0.056 (3)	0.042 (2)	0.000 (2)	−0.006 (2)	0.013 (2)
C14	0.051 (3)	0.037 (3)	0.054 (3)	−0.009 (2)	0.018 (2)	−0.012 (2)
C15	0.057 (3)	0.036 (2)	0.091 (4)	−0.006 (3)	0.035 (3)	−0.012 (3)
C18	0.049 (3)	0.048 (3)	0.079 (4)	0.011 (3)	−0.019 (3)	−0.025 (3)

Al—N1	1.922 (4)	C4—H4B	0.9700
Al—N1i	1.922 (4)	C5—C6	1.512 (8)
Al—C18i	1.961 (6)	C5—H5A	0.9700
Al—C18	1.961 (6)	C5—H5B	0.9700
N1—C1	1.346 (5)	C6—C7	1.528 (7)
N1—C2	1.465 (5)	C6—H6A	0.9700
N3—C1	1.351 (8)	C6—H6B	0.9700
N3—C14	1.477 (6)	C7—H7A	0.9700
N3—C14i	1.477 (6)	C7—H7B	0.9700
C1—N1i	1.346 (5)	C14—C15	1.526 (7)
C2—C7	1.520 (6)	C14—H14A	0.9700
C2—C3	1.531 (6)	C14—H14B	0.9700
C2—H2	0.9800	C15—C15i	1.505 (13)
C3—C4	1.517 (7)	C15—H15A	0.9700
C3—H3A	0.9700	C15—H15B	0.9700
C3—H3B	0.9700	C18—H18A	0.9600
C4—C5	1.522 (7)	C18—H18B	0.9600
C4—H4A	0.9700	C18—H18C	0.9600
N1—Al—N1i	69.8 (2)	C4—C5—H5A	109.5
N1—Al—C18i	119.0 (2)	C6—C5—H5B	109.5
N1i—Al—C18i	114.0 (2)	C4—C5—H5B	109.5
N1—Al—C18	114.0 (2)	H5A—C5—H5B	108.0
N1i—Al—C18	119.0 (2)	C5—C6—C7	111.3 (4)
C18i—Al—C18	114.2 (4)	C5—C6—H6A	109.4
C1—N1—C2	124.8 (3)	C7—C6—H6A	109.4
C1—N1—Al	90.4 (3)	C5—C6—H6B	109.4
C2—N1—Al	133.2 (3)	C7—C6—H6B	109.4
C1—N3—C14	124.0 (3)	H6A—C6—H6B	108.0
C1—N3—C14i	124.0 (3)	C2—C7—C6	112.1 (4)
C14—N3—C14i	112.0 (5)	C2—C7—H7A	109.2
N1i—C1—N1	109.4 (5)	C6—C7—H7A	109.2
N1i—C1—N3	125.3 (3)	C2—C7—H7B	109.2
N1—C1—N3	125.3 (3)	C6—C7—H7B	109.2
N1—C2—C7	108.7 (3)	H7A—C7—H7B	107.9
N1—C2—C3	112.3 (4)	N3—C14—C15	102.2 (5)
C7—C2—C3	109.3 (4)	N3—C14—H14A	111.3
N1—C2—H2	108.8	C15—C14—H14A	111.3
C7—C2—H2	108.8	N3—C14—H14B	111.3
C3—C2—H2	108.8	C15—C14—H14B	111.3
C4—C3—C2	111.9 (4)	H14A—C14—H14B	109.2
C4—C3—H3A	109.2	C15i—C15—C14	103.2 (3)
C2—C3—H3A	109.2	C15i—C15—H15A	111.1
C4—C3—H3B	109.2	C14—C15—H15A	111.1
C2—C3—H3B	109.2	C15i—C15—H15B	111.1
H3A—C3—H3B	107.9	C14—C15—H15B	111.1
C3—C4—C5	111.0 (4)	H15A—C15—H15B	109.1
C3—C4—H4A	109.4	Al—C18—H18A	109.5
C5—C4—H4A	109.4	Al—C18—H18B	109.5
C3—C4—H4B	109.4	H18A—C18—H18B	109.5
C5—C4—H4B	109.4	Al—C18—H18C	109.5
H4A—C4—H4B	108.0	H18A—C18—H18C	109.5
C6—C5—C4	110.9 (5)	H18B—C18—H18C	109.5
C6—C5—H5A	109.5
N1i—Al—N1—C1	0.0	Al—N1—C2—C7	40.9 (5)
C18i—Al—N1—C1	106.9 (2)	C1—N1—C2—C3	51.3 (5)
C18—Al—N1—C1	−113.6 (2)	Al—N1—C2—C3	−80.2 (5)
N1i—Al—N1—C2	142.0 (5)	N1—C2—C3—C4	176.7 (4)
C18i—Al—N1—C2	−111.0 (4)	C7—C2—C3—C4	55.9 (5)
C18—Al—N1—C2	28.4 (5)	C2—C3—C4—C5	−56.6 (6)
C2—N1—C1—N1i	−146.9 (4)	C3—C4—C5—C6	55.6 (7)
Al—N1—C1—N1i	0.0	C4—C5—C6—C7	−55.1 (6)
C2—N1—C1—N3	33.1 (4)	N1—C2—C7—C6	−178.3 (4)
Al—N1—C1—N3	180.0	C3—C2—C7—C6	−55.4 (5)
C14—N3—C1—N1i	−158.0 (3)	C5—C6—C7—C2	56.0 (6)
C14i—N3—C1—N1i	22.0 (3)	C1—N3—C14—C15	167.3 (2)
C14—N3—C1—N1	22.0 (3)	C14i—N3—C14—C15	−12.7 (2)
C14i—N3—C1—N1	−158.0 (3)	N3—C14—C15—C15i	33.5 (6)
C1—N1—C2—C7	172.4 (4)

Al—N1	1.922 (4)
Al—C18	1.961 (6)

N1—Al—N1i	69.8 (2)
C18i—Al—C18	114.2 (4)

Symmetry code: (i) .