A primary monomeric alane: [N,N'-bis(2,6-diiso­propyl­phenyl)­pentane-2,4-diiminato-N,N']­dihydrido­aluminium

The title compound, [AlH₂(C₂₉H₄₁N₂)], is an example of a sterically encumbered monomeric primary alane. The bond lengths are within normal ranges. The N-Al distance is 1.8989 (12) Å. The H atoms bonded to the aluminium center were located in a difference map and refined to Al-H distances of 1.51 (2) and 1.518 (19) Å. There are no significant intermolecular interactions.

Key indicators

• Single-crystal X-ray study
• T = 90 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.049
• wR factor = 0.135
• Data-to-parameter ratio = 27.7

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           31.50
         From the CIF: _reflns_number_total               8512
         TEST2: Reflns within _diffrn_reflns_theta_max
         Count of symmetry unique reflns         9073
         Completeness (_total/calc)             93.82%
          Alert C: < 95% complete


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 Alert Level C = Please check

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINTPlus (Bruker, 1999); program(s) used to solve structure: XS in SHELXTL (Sheldrick, 1998); program(s) used to refine structure: XL in SHELXTL; molecular graphics: XP in SHELXTL; software used to prepare material for publication: XCIF in SHELXTL.

(I)

Crystal data

[AlH2(C29H41N2)]	Dx = 1.088 Mg m^−3
Mr = 446.63	Melting point: 194 K
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 12.4720 (9) Å	Cell parameters from 4245 reflections
b = 16.0700 (12) Å	θ = 2.3–31.1°
c = 14.0635 (11) Å	µ = 0.09 mm^−1
β = 104.66 (2)°	T = 90 K
V = 2726.9 (4) Å^3	Cube, colorless
Z = 4	0.13 × 0.12 × 0.10 mm
F(000) = 976

Data collection

Bruker SMART 1000 diffractometer	8512 independent reflections
Radiation source: normal-focus sealed tube	5366 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.048
Detector resolution: 8.3 pixels mm^-1	θmax = 31.5°, θmin = 2.0°
ω scans	h = −18→17
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1999)	k = −23→23
Tmin = 0.988, Tmax = 0.991	l = −19→19
26394 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.135	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0604P)^2 + 0.3174P] where P = (Fo^2 + 2Fc^2)/3
8512 reflections	(Δ/σ)max = 0.001
307 parameters	Δρmax = 0.36 e Å^−3
0 restraints	Δρmin = −0.27 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
N1	0.12501 (9)	0.18487 (7)	0.84650 (8)	0.0149 (2)
C1	0.13933 (11)	0.26696 (8)	0.83925 (10)	0.0163 (3)
Al1	0.14703 (4)	0.10414 (3)	0.75467 (4)	0.02459 (12)
H1	0.0393 (16)	0.0612 (13)	0.7048 (15)	0.049 (6)*
H2	0.2397 (16)	0.0438 (12)	0.7994 (15)	0.050 (6)*
N2	0.19198 (9)	0.17998 (7)	0.66866 (8)	0.0154 (2)
C2	0.17536 (12)	0.30302 (8)	0.76191 (10)	0.0177 (3)
H2A	0.1838	0.3618	0.7639	0.021*
C3	0.20034 (11)	0.26232 (8)	0.68201 (10)	0.0161 (3)
C4	0.11569 (13)	0.32422 (9)	0.91637 (11)	0.0217 (3)
H4A	0.1569	0.3053	0.9817	0.033*
H4B	0.0361	0.3236	0.9125	0.033*
H4C	0.1387	0.3809	0.9051	0.033*
C5	0.23797 (13)	0.31563 (9)	0.60861 (11)	0.0231 (3)
H5A	0.3068	0.2929	0.5976	0.035*
H5B	0.2511	0.3725	0.6340	0.035*
H5C	0.1806	0.3162	0.5464	0.035*
C6	0.08689 (11)	0.15309 (8)	0.92883 (10)	0.0156 (3)
C7	0.16504 (12)	0.12842 (8)	1.01478 (10)	0.0175 (3)
C8	0.12557 (12)	0.09619 (9)	1.09182 (11)	0.0202 (3)
H8A	0.1770	0.0813	1.1516	0.024*
C9	0.01341 (13)	0.08551 (9)	1.08315 (11)	0.0207 (3)
H9A	−0.0116	0.0623	1.1358	0.025*
C10	−0.06201 (12)	0.10893 (8)	0.99715 (11)	0.0189 (3)
H10A	−0.1389	0.1005	0.9910	0.023*
C11	−0.02798 (11)	0.14461 (8)	0.91916 (10)	0.0162 (3)
C12	−0.11409 (11)	0.17428 (8)	0.82859 (10)	0.0185 (3)
H12A	−0.0742	0.2024	0.7842	0.022*
C13	−0.18057 (13)	0.10202 (9)	0.77182 (12)	0.0281 (3)
H13A	−0.1298	0.0618	0.7541	0.042*
H13B	−0.2317	0.1233	0.7119	0.042*
H13C	−0.2228	0.0747	0.8130	0.042*
C14	−0.19321 (13)	0.23786 (10)	0.85581 (12)	0.0263 (3)
H14A	−0.1501	0.2826	0.8951	0.039*
H14B	−0.2387	0.2103	0.8940	0.039*
H14C	−0.2414	0.2613	0.7957	0.039*
C15	0.28919 (12)	0.13502 (10)	1.02585 (11)	0.0233 (3)
H15A	0.3011	0.1625	0.9655	0.028*
C16	0.34624 (15)	0.18802 (12)	1.11478 (13)	0.0362 (4)
H16A	0.3122	0.2434	1.1089	0.054*
H16B	0.4252	0.1934	1.1173	0.054*
H16C	0.3379	0.1612	1.1751	0.054*
C17	0.34250 (14)	0.04829 (11)	1.03406 (15)	0.0375 (4)
H17A	0.3088	0.0159	0.9750	0.056*
H17B	0.3305	0.0197	1.0921	0.056*
H17C	0.4222	0.0539	1.0403	0.056*
C18	0.21798 (11)	0.14167 (8)	0.58349 (10)	0.0153 (3)
C19	0.32530 (11)	0.10944 (8)	0.59262 (10)	0.0164 (3)
C20	0.34473 (12)	0.06425 (8)	0.51377 (11)	0.0196 (3)
H20A	0.4164	0.0418	0.5187	0.024*
C21	0.26194 (12)	0.05156 (9)	0.42872 (11)	0.0209 (3)
H21A	0.2763	0.0195	0.3765	0.025*
C22	0.15775 (12)	0.08584 (9)	0.41994 (11)	0.0200 (3)
H22A	0.1017	0.0780	0.3608	0.024*
C23	0.13359 (11)	0.13165 (8)	0.49633 (10)	0.0167 (3)
C24	0.01886 (12)	0.16973 (9)	0.48226 (11)	0.0214 (3)
H24A	0.0185	0.2024	0.5427	0.026*
C25	−0.00777 (14)	0.22971 (10)	0.39450 (12)	0.0294 (4)
H25A	−0.0804	0.2553	0.3891	0.044*
H25B	−0.0090	0.1989	0.3341	0.044*
H25C	0.0491	0.2732	0.4043	0.044*
C26	−0.07134 (13)	0.10334 (11)	0.46915 (14)	0.0334 (4)
H26A	−0.1436	0.1303	0.4611	0.050*
H26B	−0.0563	0.0672	0.5272	0.050*
H26C	−0.0720	0.0699	0.4107	0.050*
C27	0.42052 (12)	0.12525 (9)	0.68205 (11)	0.0206 (3)
H27A	0.3912	0.1579	0.7305	0.025*
C28	0.51139 (13)	0.17755 (10)	0.65397 (12)	0.0276 (3)
H28A	0.4784	0.2281	0.6198	0.041*
H28B	0.5458	0.1450	0.6107	0.041*
H28C	0.5678	0.1929	0.7136	0.041*
C29	0.47128 (15)	0.04511 (11)	0.73211 (13)	0.0362 (4)
H29A	0.4143	0.0131	0.7529	0.054*
H29B	0.5315	0.0588	0.7897	0.054*
H29C	0.5006	0.0120	0.6859	0.054*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0173 (6)	0.0157 (5)	0.0126 (5)	−0.0003 (4)	0.0053 (4)	0.0006 (4)
C1	0.0141 (6)	0.0185 (6)	0.0156 (7)	0.0002 (5)	0.0027 (5)	−0.0008 (5)
Al1	0.0421 (3)	0.0155 (2)	0.0222 (2)	−0.00386 (19)	0.0194 (2)	−0.00197 (17)
N2	0.0173 (6)	0.0167 (5)	0.0135 (6)	−0.0002 (4)	0.0061 (4)	−0.0009 (4)
C2	0.0213 (7)	0.0143 (6)	0.0184 (7)	−0.0002 (5)	0.0067 (6)	0.0003 (5)
C3	0.0155 (7)	0.0175 (6)	0.0153 (7)	0.0000 (5)	0.0042 (5)	0.0016 (5)
C4	0.0280 (8)	0.0184 (6)	0.0212 (7)	−0.0016 (6)	0.0109 (6)	−0.0030 (5)
C5	0.0327 (8)	0.0191 (7)	0.0212 (8)	−0.0017 (6)	0.0140 (6)	0.0018 (5)
C6	0.0196 (7)	0.0152 (6)	0.0133 (6)	−0.0014 (5)	0.0067 (5)	−0.0012 (5)
C7	0.0202 (7)	0.0172 (6)	0.0155 (7)	−0.0006 (5)	0.0054 (5)	0.0002 (5)
C8	0.0253 (8)	0.0203 (7)	0.0145 (7)	0.0013 (6)	0.0038 (6)	0.0015 (5)
C9	0.0282 (8)	0.0191 (6)	0.0178 (7)	−0.0004 (6)	0.0114 (6)	0.0007 (5)
C10	0.0195 (7)	0.0176 (6)	0.0218 (7)	−0.0004 (5)	0.0093 (6)	−0.0026 (5)
C11	0.0179 (7)	0.0143 (6)	0.0169 (7)	0.0003 (5)	0.0056 (5)	−0.0023 (5)
C12	0.0165 (7)	0.0208 (6)	0.0181 (7)	0.0006 (5)	0.0044 (5)	−0.0007 (5)
C13	0.0253 (8)	0.0257 (7)	0.0280 (9)	0.0016 (6)	−0.0031 (7)	−0.0057 (6)
C14	0.0237 (8)	0.0276 (8)	0.0265 (8)	0.0062 (6)	0.0042 (7)	−0.0029 (6)
C15	0.0181 (7)	0.0314 (8)	0.0198 (8)	−0.0022 (6)	0.0037 (6)	0.0030 (6)
C16	0.0293 (9)	0.0450 (10)	0.0297 (10)	−0.0102 (8)	−0.0007 (7)	−0.0007 (8)
C17	0.0245 (9)	0.0417 (10)	0.0458 (12)	0.0085 (7)	0.0076 (8)	0.0074 (8)
C18	0.0185 (7)	0.0146 (6)	0.0139 (6)	−0.0011 (5)	0.0062 (5)	0.0003 (5)
C19	0.0176 (7)	0.0168 (6)	0.0156 (7)	0.0001 (5)	0.0056 (5)	0.0013 (5)
C20	0.0190 (7)	0.0195 (6)	0.0214 (7)	0.0024 (5)	0.0071 (6)	−0.0008 (5)
C21	0.0245 (8)	0.0206 (7)	0.0200 (7)	−0.0024 (6)	0.0100 (6)	−0.0060 (5)
C22	0.0197 (7)	0.0243 (7)	0.0153 (7)	−0.0036 (5)	0.0030 (5)	−0.0034 (5)
C23	0.0166 (7)	0.0176 (6)	0.0163 (7)	−0.0009 (5)	0.0048 (5)	0.0004 (5)
C24	0.0176 (7)	0.0265 (7)	0.0196 (7)	0.0028 (6)	0.0041 (6)	−0.0008 (6)
C25	0.0265 (8)	0.0328 (8)	0.0280 (9)	0.0061 (7)	0.0053 (7)	0.0081 (7)
C26	0.0165 (8)	0.0369 (9)	0.0462 (11)	0.0008 (7)	0.0069 (7)	0.0047 (8)
C27	0.0171 (7)	0.0268 (7)	0.0168 (7)	0.0013 (5)	0.0022 (6)	−0.0006 (5)
C28	0.0203 (8)	0.0326 (8)	0.0273 (9)	−0.0043 (6)	0.0011 (6)	−0.0009 (6)
C29	0.0334 (10)	0.0368 (9)	0.0319 (10)	0.0018 (8)	−0.0036 (8)	0.0117 (7)

Geometric parameters (Å, º)

N1—C1	1.3386 (17)	C15—C16	1.531 (2)
N1—C6	1.4511 (16)	C15—C17	1.536 (2)
N1—Al1	1.8989 (12)	C15—H15A	1.0000
C1—C2	1.4030 (18)	C16—H16A	0.9800
C1—C4	1.5072 (19)	C16—H16B	0.9800
Al1—N2	1.8989 (12)	C16—H16C	0.9800
Al1—H1	1.51 (2)	C17—H17A	0.9800
Al1—H2	1.518 (19)	C17—H17B	0.9800
N2—C3	1.3369 (17)	C17—H17C	0.9800
N2—C18	1.4544 (16)	C18—C23	1.4083 (19)
C2—C3	1.4017 (18)	C18—C19	1.4104 (19)
C2—H2A	0.9500	C19—C20	1.3970 (19)
C3—C5	1.5048 (18)	C19—C27	1.517 (2)
C4—H4A	0.9800	C20—C21	1.383 (2)
C4—H4B	0.9800	C20—H20A	0.9500
C4—H4C	0.9800	C21—C22	1.388 (2)
C5—H5A	0.9800	C21—H21A	0.9500
C5—H5B	0.9800	C22—C23	1.3968 (19)
C5—H5C	0.9800	C22—H22A	0.9500
C6—C7	1.404 (2)	C23—C24	1.5224 (19)
C6—C11	1.4111 (19)	C24—C26	1.527 (2)
C7—C8	1.3980 (19)	C24—C25	1.535 (2)
C7—C15	1.520 (2)	C24—H24A	1.0000
C8—C9	1.384 (2)	C25—H25A	0.9800
C8—H8A	0.9500	C25—H25B	0.9800
C9—C10	1.383 (2)	C25—H25C	0.9800
C9—H9A	0.9500	C26—H26A	0.9800
C10—C11	1.3956 (19)	C26—H26B	0.9800
C10—H10A	0.9500	C26—H26C	0.9800
C11—C12	1.520 (2)	C27—C29	1.526 (2)
C12—C13	1.529 (2)	C27—C28	1.541 (2)
C12—C14	1.5347 (19)	C27—H27A	1.0000
C12—H12A	1.0000	C28—H28A	0.9800
C13—H13A	0.9800	C28—H28B	0.9800
C13—H13B	0.9800	C28—H28C	0.9800
C13—H13C	0.9800	C29—H29A	0.9800
C14—H14A	0.9800	C29—H29B	0.9800
C14—H14B	0.9800	C29—H29C	0.9800
C14—H14C	0.9800
C1—N1—C6	118.98 (11)	C16—C15—C17	109.91 (14)
C1—N1—Al1	125.20 (9)	C7—C15—H15A	108.0
C6—N1—Al1	115.80 (8)	C16—C15—H15A	108.0
N1—C1—C2	122.77 (12)	C17—C15—H15A	108.0
N1—C1—C4	119.52 (12)	C15—C16—H16A	109.5
C2—C1—C4	117.71 (12)	C15—C16—H16B	109.5
N1—Al1—N2	96.41 (5)	H16A—C16—H16B	109.5
N1—Al1—H1	111.2 (7)	C15—C16—H16C	109.5
N2—Al1—H1	111.6 (8)	H16A—C16—H16C	109.5
N1—Al1—H2	112.4 (8)	H16B—C16—H16C	109.5
N2—Al1—H2	110.9 (7)	C15—C17—H17A	109.5
H1—Al1—H2	113.2 (11)	C15—C17—H17B	109.5
C3—N2—C18	120.59 (11)	H17A—C17—H17B	109.5
C3—N2—Al1	124.81 (9)	C15—C17—H17C	109.5
C18—N2—Al1	114.60 (8)	H17A—C17—H17C	109.5
C3—C2—C1	127.48 (12)	H17B—C17—H17C	109.5
C3—C2—H2A	116.3	C23—C18—C19	121.36 (12)
C1—C2—H2A	116.3	C23—C18—N2	119.46 (12)
N2—C3—C2	123.31 (12)	C19—C18—N2	118.99 (12)
N2—C3—C5	119.60 (12)	C20—C19—C18	118.02 (13)
C2—C3—C5	117.09 (12)	C20—C19—C27	119.25 (12)
C1—C4—H4A	109.5	C18—C19—C27	122.67 (12)
C1—C4—H4B	109.5	C21—C20—C19	121.44 (13)
H4A—C4—H4B	109.5	C21—C20—H20A	119.3
C1—C4—H4C	109.5	C19—C20—H20A	119.3
H4A—C4—H4C	109.5	C20—C21—C22	119.72 (13)
H4B—C4—H4C	109.5	C20—C21—H21A	120.1
C3—C5—H5A	109.5	C22—C21—H21A	120.1
C3—C5—H5B	109.5	C21—C22—C23	121.35 (13)
H5A—C5—H5B	109.5	C21—C22—H22A	119.3
C3—C5—H5C	109.5	C23—C22—H22A	119.3
H5A—C5—H5C	109.5	C22—C23—C18	118.06 (12)
H5B—C5—H5C	109.5	C22—C23—C24	119.37 (13)
C7—C6—C11	121.49 (12)	C18—C23—C24	122.56 (12)
C7—C6—N1	119.34 (12)	C23—C24—C26	111.98 (12)
C11—C6—N1	119.12 (12)	C23—C24—C25	111.23 (12)
C8—C7—C6	117.90 (13)	C26—C24—C25	109.80 (13)
C8—C7—C15	119.72 (13)	C23—C24—H24A	107.9
C6—C7—C15	122.38 (12)	C26—C24—H24A	107.9
C9—C8—C7	121.60 (14)	C25—C24—H24A	107.9
C9—C8—H8A	119.2	C24—C25—H25A	109.5
C7—C8—H8A	119.2	C24—C25—H25B	109.5
C10—C9—C8	119.47 (13)	H25A—C25—H25B	109.5
C10—C9—H9A	120.3	C24—C25—H25C	109.5
C8—C9—H9A	120.3	H25A—C25—H25C	109.5
C9—C10—C11	121.61 (13)	H25B—C25—H25C	109.5
C9—C10—H10A	119.2	C24—C26—H26A	109.5
C11—C10—H10A	119.2	C24—C26—H26B	109.5
C10—C11—C6	117.86 (13)	H26A—C26—H26B	109.5
C10—C11—C12	119.77 (12)	C24—C26—H26C	109.5
C6—C11—C12	122.37 (12)	H26A—C26—H26C	109.5
C11—C12—C13	111.97 (12)	H26B—C26—H26C	109.5
C11—C12—C14	111.25 (12)	C19—C27—C29	112.80 (13)
C13—C12—C14	109.74 (12)	C19—C27—C28	110.56 (12)
C11—C12—H12A	107.9	C29—C27—C28	109.41 (13)
C13—C12—H12A	107.9	C19—C27—H27A	108.0
C14—C12—H12A	107.9	C29—C27—H27A	108.0
C12—C13—H13A	109.5	C28—C27—H27A	108.0
C12—C13—H13B	109.5	C27—C28—H28A	109.5
H13A—C13—H13B	109.5	C27—C28—H28B	109.5
C12—C13—H13C	109.5	H28A—C28—H28B	109.5
H13A—C13—H13C	109.5	C27—C28—H28C	109.5
H13B—C13—H13C	109.5	H28A—C28—H28C	109.5
C12—C14—H14A	109.5	H28B—C28—H28C	109.5
C12—C14—H14B	109.5	C27—C29—H29A	109.5
H14A—C14—H14B	109.5	C27—C29—H29B	109.5
C12—C14—H14C	109.5	H29A—C29—H29B	109.5
H14A—C14—H14C	109.5	C27—C29—H29C	109.5
H14B—C14—H14C	109.5	H29A—C29—H29C	109.5
C7—C15—C16	111.92 (13)	H29B—C29—H29C	109.5
C7—C15—C17	110.77 (13)