metal-organic compounds
Bis(μ-diisopropylhydoxylaminato)-κ2O:N;κ2O:O-bis[(diisopropylhydoxylaminato-κO)beryllium]
aFachbereich für Materialwissenschaften und Physik, Paris-Lodron Universität Salzburg, 5020 Salzburg, Austria, bDepartment of Chemistry, Asansol Girls' College, Asansol 713 304, West Bengal, India, cInstitut für Anorganische Chemie, Johannes-Kepler-Universität Linz, Altenbergerstrasse 69, 4040 Linz, Austria, and dLehrstuhl für Anorganische Chemie und Strukturchemie, Universität Bielefeld, 33615 Bielefeld, Germany
*Correspondence e-mail: raphael.berger@sbg.ac.at
The title compound, [Be2(C6H14NO)4], was prepared from a solution of BeCl2 in diethyl ether and two equivalents of O-lithiated N,N-diisopropylhydoxylamine. The molecular structure is composed of a dinuclear unit forming a central five-membered planar Be—O—Be—O—N ring (sum of internal angles = 540.0°; r.m.s. deviation from planarity = 0.0087 Å). Both Be atoms show the unusual of three, with one Be atom coordinated by three O atoms and the other by two O atoms and one N atom, both in distorted trigonal–planar environments. The Be—O distances are in the range 1.493 (5)–1.600 (5) Å and the Be—N distance is 1.741 (5) Å.
Related literature
For general background to metal compounds containing hydroxylamine ligands, see: Ullrich (2007). For further information on beryllium coordination compounds, see: Berger, Hartmann et al. (2001); Berger, Schmidt et al. (2001); Dressel et al. (2003); Berger et al. (2011); for information about coordination compounds containing Be—N bonds, see: Dressel et al. (2003); Neumüller & Dehnicke (2010).
Experimental
Crystal data
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Data collection: X-AREA (Stoe & Cie, 2012); cell X-AREA; data reduction: X-RED32 (Stoe & Cie, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: publCIF (Westrip, 2010).
Supporting information
10.1107/S1600536812045655/wm2695sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812045655/wm2695Isup2.hkl
A suspension of 1.282 g (4 mmol) Li(ONiPr2) in 15 ml of dry diethyl ether was slowly dropped to a solution of 159 mg BeCl2 (2 mmol) in 5 ml diethyl ether. The reaction mixture was stirred for 6 h at room temperature and filtered using a syringe equipped with a Whatmann glass filter. The clear solution was reduced in vacuo to about 15 ml and stored at 243 K for two weeks. Clear colorless block-shaped crystals were collected from the solution under an argon atmosphere. The material is extremely water- and moist-sensitive and must be handled under inert gas.
All H atoms were treated as riding with C—H distances of 0.97 (C—H), 0.98 (CH3), and Uiso(H) = 1.2 Ueq(C) [1.5 Ueq for methyl hydrogen atoms]. Riding methyl hydrogen atoms were allowed to rotate freely during refinement.
Data collection: X-AREA (Stoe & Cie, 2012); cell
X-AREA (Stoe & Cie, 2012); data reduction: X-RED32 (Stoe & Cie, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: publCIF (Westrip, 2010).Fig. 1. The dinuclear molecular unit of the title compound. Atoms are displayed with displacement ellipsoids at the 10% probability level. Hydrogen atoms have been omitted for clarity. |
[Be2(C6H14NO)4] | Z = 2 |
Mr = 482.75 | F(000) = 536 |
Triclinic, P1 | Dx = 1.081 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.2156 (17) Å | Cell parameters from 5000 reflections |
b = 13.248 (3) Å | θ = 4.3–25.2° |
c = 14.317 (3) Å | µ = 0.07 mm−1 |
α = 98.82 (2)° | T = 110 K |
β = 97.42 (2)° | Block, colourless |
γ = 102.42 (2)° | 0.20 × 0.10 × 0.05 mm |
V = 1482.5 (5) Å3 |
Stoe IPDS diffractometer | 2359 reflections with I > 2σ(I) |
Radiation source: sealed tube | Rint = 0.162 |
Graphite monochromator | θmax = 25.8°, θmin = 4.2° |
rotation scans | h = −10→9 |
20278 measured reflections | k = −16→16 |
5220 independent reflections | l = −17→17 |
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)] = 0.061 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.169 | H-atom parameters constrained |
S = 0.98 | w = 1/[σ2(Fo2) + (0.0603P)2] where P = (Fo2 + 2Fc2)/3 |
5220 reflections | (Δ/σ)max < 0.001 |
323 parameters | Δρmax = 0.17 e Å−3 |
0 restraints | Δρmin = −0.22 e Å−3 |
0 constraints |
[Be2(C6H14NO)4] | γ = 102.42 (2)° |
Mr = 482.75 | V = 1482.5 (5) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.2156 (17) Å | Mo Kα radiation |
b = 13.248 (3) Å | µ = 0.07 mm−1 |
c = 14.317 (3) Å | T = 110 K |
α = 98.82 (2)° | 0.20 × 0.10 × 0.05 mm |
β = 97.42 (2)° |
Stoe IPDS diffractometer | 2359 reflections with I > 2σ(I) |
20278 measured reflections | Rint = 0.162 |
5220 independent reflections |
R[F2 > 2σ(F2)] = 0.061 | 0 restraints |
wR(F2) = 0.169 | H-atom parameters constrained |
S = 0.98 | Δρmax = 0.17 e Å−3 |
5220 reflections | Δρmin = −0.22 e Å−3 |
323 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.0493 (3) | 0.11429 (16) | 0.64521 (17) | 0.0425 (6) | |
N1 | 0.1242 (3) | 0.1998 (2) | 0.6006 (2) | 0.0406 (7) | |
Be1 | 0.2326 (6) | 0.3041 (3) | 0.6921 (3) | 0.0413 (11) | |
O2 | 0.0366 (3) | 0.07170 (16) | 0.82450 (17) | 0.0454 (6) | |
N2 | −0.0419 (3) | −0.03765 (19) | 0.7809 (2) | 0.0415 (7) | |
Be2 | 0.0876 (5) | 0.1400 (3) | 0.7543 (3) | 0.0399 (11) | |
O3 | 0.1982 (3) | 0.25866 (16) | 0.78337 (17) | 0.0415 (6) | |
N3 | 0.2877 (4) | 0.3196 (2) | 0.8786 (2) | 0.0437 (7) | |
O4 | 0.3156 (3) | 0.39645 (16) | 0.65618 (18) | 0.0449 (6) | |
N4 | 0.3860 (3) | 0.50261 (19) | 0.7113 (2) | 0.0408 (7) | |
C11 | 0.2354 (4) | 0.1547 (3) | 0.5371 (3) | 0.0446 (9) | |
H11 | 0.1673 | 0.0866 | 0.4967 | 0.054* | |
C12 | 0.3817 (5) | 0.1326 (3) | 0.6004 (3) | 0.0560 (10) | |
H12A | 0.4490 | 0.0977 | 0.5603 | 0.084* | |
H12B | 0.3376 | 0.0869 | 0.6437 | 0.084* | |
H12C | 0.4529 | 0.1991 | 0.6382 | 0.084* | |
C13 | 0.3003 (6) | 0.2276 (3) | 0.4717 (3) | 0.0601 (11) | |
H13A | 0.2059 | 0.2320 | 0.4244 | 0.090* | |
H13B | 0.3835 | 0.2003 | 0.4386 | 0.090* | |
H13C | 0.3537 | 0.2977 | 0.5097 | 0.090* | |
C14 | −0.0187 (4) | 0.2287 (3) | 0.5431 (3) | 0.0468 (9) | |
H14 | 0.0312 | 0.2870 | 0.5109 | 0.056* | |
C15 | −0.1278 (5) | 0.2706 (3) | 0.6101 (3) | 0.0577 (11) | |
H15A | −0.1862 | 0.2133 | 0.6386 | 0.087* | |
H15B | −0.2114 | 0.2990 | 0.5739 | 0.087* | |
H15C | −0.0563 | 0.3264 | 0.6610 | 0.087* | |
C16 | −0.1257 (5) | 0.1398 (3) | 0.4662 (3) | 0.0623 (12) | |
H16A | −0.0545 | 0.1152 | 0.4222 | 0.094* | |
H16B | −0.2144 | 0.1648 | 0.4305 | 0.094* | |
H16C | −0.1778 | 0.0818 | 0.4959 | 0.094* | |
C21 | 0.0464 (5) | −0.1004 (3) | 0.8373 (3) | 0.0476 (9) | |
H21 | 0.0360 | −0.0819 | 0.9064 | 0.057* | |
C22 | −0.0306 (5) | −0.2169 (3) | 0.8010 (3) | 0.0647 (12) | |
H22A | −0.1447 | −0.2352 | 0.8167 | 0.097* | |
H22B | 0.0397 | −0.2577 | 0.8316 | 0.097* | |
H22C | −0.0365 | −0.2330 | 0.7314 | 0.097* | |
C23 | 0.2317 (5) | −0.0756 (3) | 0.8273 (3) | 0.0619 (11) | |
H23A | 0.2415 | −0.0873 | 0.7592 | 0.093* | |
H23B | 0.2889 | −0.1215 | 0.8598 | 0.093* | |
H23C | 0.2844 | −0.0019 | 0.8565 | 0.093* | |
C24 | −0.2226 (4) | −0.0542 (3) | 0.7891 (3) | 0.0484 (10) | |
H24 | −0.2763 | −0.1304 | 0.7633 | 0.058* | |
C25 | −0.3057 (5) | 0.0085 (3) | 0.7246 (3) | 0.0576 (11) | |
H25A | −0.2711 | 0.0834 | 0.7537 | 0.086* | |
H25B | −0.4289 | −0.0157 | 0.7170 | 0.086* | |
H25C | −0.2705 | −0.0019 | 0.6617 | 0.086* | |
C26 | −0.2600 (5) | −0.0305 (3) | 0.8900 (3) | 0.0624 (11) | |
H26A | −0.2184 | −0.0779 | 0.9283 | 0.094* | |
H26B | −0.3823 | −0.0409 | 0.8878 | 0.094* | |
H26C | −0.2034 | 0.0425 | 0.9193 | 0.094* | |
C31 | 0.1634 (5) | 0.3670 (3) | 0.9256 (3) | 0.0508 (10) | |
H31 | 0.2247 | 0.4063 | 0.9902 | 0.061* | |
C32 | 0.1153 (5) | 0.4483 (3) | 0.8714 (3) | 0.0613 (11) | |
H32A | 0.2171 | 0.4911 | 0.8552 | 0.092* | |
H32B | 0.0613 | 0.4936 | 0.9114 | 0.092* | |
H32C | 0.0364 | 0.4129 | 0.8124 | 0.092* | |
C33 | 0.0087 (6) | 0.2913 (3) | 0.9430 (4) | 0.0710 (13) | |
H33A | −0.0626 | 0.2561 | 0.8815 | 0.106* | |
H33B | −0.0554 | 0.3302 | 0.9821 | 0.106* | |
H33C | 0.0441 | 0.2386 | 0.9768 | 0.106* | |
C34 | 0.3584 (5) | 0.2466 (3) | 0.9307 (3) | 0.0508 (10) | |
H34 | 0.2658 | 0.1855 | 0.9350 | 0.061* | |
C35 | 0.4895 (5) | 0.2079 (3) | 0.8798 (3) | 0.0597 (11) | |
H35A | 0.4369 | 0.1708 | 0.8147 | 0.090* | |
H35B | 0.5359 | 0.1598 | 0.9151 | 0.090* | |
H35C | 0.5806 | 0.2679 | 0.8765 | 0.090* | |
C36 | 0.4425 (6) | 0.3052 (4) | 1.0308 (3) | 0.0769 (14) | |
H36A | 0.5129 | 0.3737 | 1.0267 | 0.115* | |
H36B | 0.5132 | 0.2641 | 1.0606 | 0.115* | |
H36C | 0.3555 | 0.3158 | 1.0696 | 0.115* | |
C41 | 0.3229 (4) | 0.5723 (3) | 0.6515 (3) | 0.0467 (9) | |
H41 | 0.3582 | 0.5599 | 0.5872 | 0.056* | |
C42 | 0.1321 (5) | 0.5490 (3) | 0.6387 (3) | 0.0613 (11) | |
H42A | 0.0842 | 0.4764 | 0.6048 | 0.092* | |
H42B | 0.0914 | 0.5974 | 0.6013 | 0.092* | |
H42C | 0.0969 | 0.5581 | 0.7017 | 0.092* | |
C43 | 0.3965 (5) | 0.6860 (3) | 0.6994 (3) | 0.0624 (12) | |
H43A | 0.3752 | 0.6961 | 0.7656 | 0.094* | |
H43B | 0.3433 | 0.7316 | 0.6642 | 0.094* | |
H43C | 0.5186 | 0.7039 | 0.6994 | 0.094* | |
C44 | 0.5723 (4) | 0.5197 (3) | 0.7237 (3) | 0.0470 (9) | |
H44 | 0.6210 | 0.5937 | 0.7584 | 0.056* | |
C45 | 0.6278 (5) | 0.4488 (3) | 0.7884 (3) | 0.0603 (11) | |
H45A | 0.5682 | 0.4513 | 0.8434 | 0.090* | |
H45B | 0.7500 | 0.4728 | 0.8111 | 0.090* | |
H45C | 0.6013 | 0.3764 | 0.7526 | 0.090* | |
C46 | 0.6461 (5) | 0.5079 (3) | 0.6317 (3) | 0.0604 (11) | |
H46A | 0.5945 | 0.4380 | 0.5929 | 0.091* | |
H46B | 0.7686 | 0.5165 | 0.6475 | 0.091* | |
H46C | 0.6230 | 0.5618 | 0.5955 | 0.091* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0456 (13) | 0.0334 (12) | 0.0449 (16) | 0.0015 (10) | 0.0067 (11) | 0.0084 (10) |
N1 | 0.0435 (15) | 0.0342 (14) | 0.0440 (19) | 0.0069 (12) | 0.0066 (13) | 0.0109 (12) |
Be1 | 0.040 (2) | 0.037 (2) | 0.042 (3) | 0.0016 (19) | 0.009 (2) | 0.0029 (19) |
O2 | 0.0464 (14) | 0.0352 (12) | 0.0473 (16) | 0.0003 (10) | 0.0035 (11) | 0.0022 (10) |
N2 | 0.0387 (15) | 0.0319 (14) | 0.049 (2) | 0.0029 (12) | 0.0026 (14) | 0.0058 (13) |
Be2 | 0.038 (2) | 0.038 (2) | 0.041 (3) | 0.0036 (18) | 0.005 (2) | 0.0078 (19) |
O3 | 0.0405 (12) | 0.0366 (12) | 0.0399 (15) | 0.0030 (10) | −0.0006 (10) | −0.0006 (10) |
N3 | 0.0471 (17) | 0.0424 (16) | 0.0347 (18) | 0.0055 (13) | −0.0002 (14) | −0.0011 (12) |
O4 | 0.0483 (13) | 0.0320 (12) | 0.0477 (16) | 0.0022 (10) | 0.0048 (11) | 0.0003 (10) |
N4 | 0.0420 (15) | 0.0273 (14) | 0.0484 (19) | 0.0031 (11) | 0.0020 (13) | 0.0050 (12) |
C11 | 0.049 (2) | 0.0362 (18) | 0.045 (2) | 0.0063 (15) | 0.0083 (17) | 0.0022 (15) |
C12 | 0.052 (2) | 0.053 (2) | 0.060 (3) | 0.0120 (18) | 0.0070 (19) | 0.0014 (18) |
C13 | 0.075 (3) | 0.050 (2) | 0.055 (3) | 0.008 (2) | 0.021 (2) | 0.0089 (18) |
C14 | 0.048 (2) | 0.0366 (18) | 0.051 (2) | 0.0068 (15) | −0.0053 (18) | 0.0097 (16) |
C15 | 0.047 (2) | 0.054 (2) | 0.071 (3) | 0.0150 (18) | 0.005 (2) | 0.010 (2) |
C16 | 0.065 (3) | 0.051 (2) | 0.062 (3) | 0.0111 (19) | −0.012 (2) | 0.0035 (19) |
C21 | 0.051 (2) | 0.0422 (19) | 0.047 (2) | 0.0076 (16) | 0.0034 (18) | 0.0115 (16) |
C22 | 0.069 (3) | 0.045 (2) | 0.075 (3) | 0.0069 (19) | 0.003 (2) | 0.012 (2) |
C23 | 0.050 (2) | 0.059 (2) | 0.076 (3) | 0.0136 (19) | 0.008 (2) | 0.010 (2) |
C24 | 0.0353 (19) | 0.047 (2) | 0.058 (3) | 0.0014 (15) | 0.0062 (18) | 0.0097 (17) |
C25 | 0.048 (2) | 0.062 (2) | 0.064 (3) | 0.0139 (18) | 0.004 (2) | 0.015 (2) |
C26 | 0.054 (2) | 0.072 (3) | 0.066 (3) | 0.012 (2) | 0.020 (2) | 0.020 (2) |
C31 | 0.055 (2) | 0.049 (2) | 0.043 (2) | 0.0100 (17) | 0.0112 (18) | −0.0044 (17) |
C32 | 0.057 (2) | 0.057 (2) | 0.068 (3) | 0.0160 (19) | 0.013 (2) | 0.003 (2) |
C33 | 0.073 (3) | 0.063 (3) | 0.079 (4) | 0.014 (2) | 0.038 (3) | 0.004 (2) |
C34 | 0.055 (2) | 0.052 (2) | 0.042 (2) | 0.0074 (18) | 0.0027 (18) | 0.0120 (17) |
C35 | 0.055 (2) | 0.059 (2) | 0.065 (3) | 0.0181 (19) | −0.001 (2) | 0.016 (2) |
C36 | 0.090 (3) | 0.074 (3) | 0.054 (3) | 0.016 (2) | −0.018 (2) | 0.001 (2) |
C41 | 0.050 (2) | 0.0396 (19) | 0.050 (2) | 0.0095 (16) | 0.0088 (18) | 0.0101 (16) |
C42 | 0.048 (2) | 0.056 (2) | 0.078 (3) | 0.0118 (18) | −0.002 (2) | 0.018 (2) |
C43 | 0.064 (3) | 0.038 (2) | 0.078 (3) | 0.0074 (18) | 0.000 (2) | 0.0071 (19) |
C44 | 0.0338 (18) | 0.0428 (19) | 0.059 (3) | 0.0017 (15) | 0.0042 (17) | 0.0068 (17) |
C45 | 0.045 (2) | 0.067 (3) | 0.066 (3) | 0.0125 (19) | 0.002 (2) | 0.015 (2) |
C46 | 0.050 (2) | 0.060 (2) | 0.075 (3) | 0.0095 (19) | 0.021 (2) | 0.018 (2) |
O1—N1 | 1.447 (3) | C24—C26 | 1.516 (6) |
O1—Be2 | 1.522 (5) | C24—C25 | 1.525 (5) |
N1—C14 | 1.498 (4) | C24—H24 | 1.0000 |
N1—C11 | 1.517 (5) | C25—H25A | 0.9800 |
N1—Be1 | 1.741 (5) | C25—H25B | 0.9800 |
Be1—O4 | 1.467 (5) | C25—H25C | 0.9800 |
Be1—O3 | 1.554 (5) | C26—H26A | 0.9800 |
Be1—Be2 | 2.587 (6) | C26—H26B | 0.9800 |
O2—N2 | 1.457 (3) | C26—H26C | 0.9800 |
O2—Be2 | 1.493 (5) | C31—C32 | 1.509 (6) |
N2—C24 | 1.476 (4) | C31—C33 | 1.514 (5) |
N2—C21 | 1.478 (4) | C31—H31 | 1.0000 |
Be2—O3 | 1.600 (5) | C32—H32A | 0.9800 |
O3—N3 | 1.483 (3) | C32—H32B | 0.9800 |
N3—C34 | 1.476 (5) | C32—H32C | 0.9800 |
N3—C31 | 1.488 (5) | C33—H33A | 0.9800 |
O4—N4 | 1.459 (3) | C33—H33B | 0.9800 |
N4—C41 | 1.479 (4) | C33—H33C | 0.9800 |
N4—C44 | 1.481 (4) | C34—C35 | 1.510 (6) |
C11—C13 | 1.509 (5) | C34—C36 | 1.518 (5) |
C11—C12 | 1.517 (5) | C34—H34 | 1.0000 |
C11—H11 | 1.0000 | C35—H35A | 0.9800 |
C12—H12A | 0.9800 | C35—H35B | 0.9800 |
C12—H12B | 0.9800 | C35—H35C | 0.9800 |
C12—H12C | 0.9800 | C36—H36A | 0.9800 |
C13—H13A | 0.9800 | C36—H36B | 0.9800 |
C13—H13B | 0.9800 | C36—H36C | 0.9800 |
C13—H13C | 0.9800 | C41—C42 | 1.512 (5) |
C14—C16 | 1.511 (5) | C41—C43 | 1.514 (5) |
C14—C15 | 1.517 (6) | C41—H41 | 1.0000 |
C14—H14 | 1.0000 | C42—H42A | 0.9800 |
C15—H15A | 0.9800 | C42—H42B | 0.9800 |
C15—H15B | 0.9800 | C42—H42C | 0.9800 |
C15—H15C | 0.9800 | C43—H43A | 0.9800 |
C16—H16A | 0.9800 | C43—H43B | 0.9800 |
C16—H16B | 0.9800 | C43—H43C | 0.9800 |
C16—H16C | 0.9800 | C44—C45 | 1.513 (5) |
C21—C22 | 1.517 (5) | C44—C46 | 1.520 (6) |
C21—C23 | 1.517 (5) | C44—H44 | 1.0000 |
C21—H21 | 1.0000 | C45—H45A | 0.9800 |
C22—H22A | 0.9800 | C45—H45B | 0.9800 |
C22—H22B | 0.9800 | C45—H45C | 0.9800 |
C22—H22C | 0.9800 | C46—H46A | 0.9800 |
C23—H23A | 0.9800 | C46—H46B | 0.9800 |
C23—H23B | 0.9800 | C46—H46C | 0.9800 |
C23—H23C | 0.9800 | ||
N1—O1—Be2 | 113.4 (2) | C26—C24—C25 | 110.5 (3) |
O1—N1—C14 | 106.6 (2) | N2—C24—H24 | 107.0 |
O1—N1—C11 | 105.0 (2) | C26—C24—H24 | 107.0 |
C14—N1—C11 | 111.8 (3) | C25—C24—H24 | 107.0 |
O1—N1—Be1 | 107.4 (3) | C24—C25—H25A | 109.5 |
C14—N1—Be1 | 110.8 (3) | C24—C25—H25B | 109.5 |
C11—N1—Be1 | 114.6 (3) | H25A—C25—H25B | 109.5 |
O4—Be1—O3 | 144.9 (3) | C24—C25—H25C | 109.5 |
O4—Be1—N1 | 112.9 (3) | H25A—C25—H25C | 109.5 |
O3—Be1—N1 | 102.2 (3) | H25B—C25—H25C | 109.5 |
O4—Be1—Be2 | 179.4 (3) | C24—C26—H26A | 109.5 |
O3—Be1—Be2 | 35.46 (16) | C24—C26—H26B | 109.5 |
N1—Be1—Be2 | 66.72 (19) | H26A—C26—H26B | 109.5 |
N2—O2—Be2 | 113.9 (3) | C24—C26—H26C | 109.5 |
O2—N2—C24 | 106.3 (3) | H26A—C26—H26C | 109.5 |
O2—N2—C21 | 105.3 (2) | H26B—C26—H26C | 109.5 |
C24—N2—C21 | 112.7 (3) | N3—C31—C32 | 109.3 (3) |
O2—Be2—O1 | 129.0 (3) | N3—C31—C33 | 116.6 (3) |
O2—Be2—O3 | 124.3 (3) | C32—C31—C33 | 111.5 (4) |
O1—Be2—O3 | 106.7 (3) | N3—C31—H31 | 106.2 |
O2—Be2—Be1 | 158.5 (3) | C32—C31—H31 | 106.2 |
O1—Be2—Be1 | 72.4 (2) | C33—C31—H31 | 106.2 |
O3—Be2—Be1 | 34.30 (16) | C31—C32—H32A | 109.5 |
N3—O3—Be1 | 119.2 (2) | C31—C32—H32B | 109.5 |
N3—O3—Be2 | 129.8 (3) | H32A—C32—H32B | 109.5 |
Be1—O3—Be2 | 110.2 (3) | C31—C32—H32C | 109.5 |
C34—N3—O3 | 107.3 (2) | H32A—C32—H32C | 109.5 |
C34—N3—C31 | 114.6 (3) | H32B—C32—H32C | 109.5 |
O3—N3—C31 | 107.2 (2) | C31—C33—H33A | 109.5 |
N4—O4—Be1 | 126.9 (3) | C31—C33—H33B | 109.5 |
O4—N4—C41 | 104.9 (2) | H33A—C33—H33B | 109.5 |
O4—N4—C44 | 106.6 (3) | C31—C33—H33C | 109.5 |
C41—N4—C44 | 112.3 (3) | H33A—C33—H33C | 109.5 |
C13—C11—N1 | 112.1 (3) | H33B—C33—H33C | 109.5 |
C13—C11—C12 | 110.4 (3) | N3—C34—C35 | 110.1 (3) |
N1—C11—C12 | 108.7 (3) | N3—C34—C36 | 108.6 (3) |
C13—C11—H11 | 108.5 | C35—C34—C36 | 108.8 (4) |
N1—C11—H11 | 108.5 | N3—C34—H34 | 109.8 |
C12—C11—H11 | 108.5 | C35—C34—H34 | 109.8 |
C11—C12—H12A | 109.5 | C36—C34—H34 | 109.8 |
C11—C12—H12B | 109.5 | C34—C35—H35A | 109.5 |
H12A—C12—H12B | 109.5 | C34—C35—H35B | 109.5 |
C11—C12—H12C | 109.5 | H35A—C35—H35B | 109.5 |
H12A—C12—H12C | 109.5 | C34—C35—H35C | 109.5 |
H12B—C12—H12C | 109.5 | H35A—C35—H35C | 109.5 |
C11—C13—H13A | 109.5 | H35B—C35—H35C | 109.5 |
C11—C13—H13B | 109.5 | C34—C36—H36A | 109.5 |
H13A—C13—H13B | 109.5 | C34—C36—H36B | 109.5 |
C11—C13—H13C | 109.5 | H36A—C36—H36B | 109.5 |
H13A—C13—H13C | 109.5 | C34—C36—H36C | 109.5 |
H13B—C13—H13C | 109.5 | H36A—C36—H36C | 109.5 |
N1—C14—C16 | 113.9 (3) | H36B—C36—H36C | 109.5 |
N1—C14—C15 | 109.4 (3) | N4—C41—C42 | 109.9 (3) |
C16—C14—C15 | 110.3 (3) | N4—C41—C43 | 109.6 (3) |
N1—C14—H14 | 107.7 | C42—C41—C43 | 109.5 (3) |
C16—C14—H14 | 107.7 | N4—C41—H41 | 109.3 |
C15—C14—H14 | 107.7 | C42—C41—H41 | 109.3 |
C14—C15—H15A | 109.5 | C43—C41—H41 | 109.3 |
C14—C15—H15B | 109.5 | C41—C42—H42A | 109.5 |
H15A—C15—H15B | 109.5 | C41—C42—H42B | 109.5 |
C14—C15—H15C | 109.5 | H42A—C42—H42B | 109.5 |
H15A—C15—H15C | 109.5 | C41—C42—H42C | 109.5 |
H15B—C15—H15C | 109.5 | H42A—C42—H42C | 109.5 |
C14—C16—H16A | 109.5 | H42B—C42—H42C | 109.5 |
C14—C16—H16B | 109.5 | C41—C43—H43A | 109.5 |
H16A—C16—H16B | 109.5 | C41—C43—H43B | 109.5 |
C14—C16—H16C | 109.5 | H43A—C43—H43B | 109.5 |
H16A—C16—H16C | 109.5 | C41—C43—H43C | 109.5 |
H16B—C16—H16C | 109.5 | H43A—C43—H43C | 109.5 |
N2—C21—C22 | 110.1 (3) | H43B—C43—H43C | 109.5 |
N2—C21—C23 | 109.0 (3) | N4—C44—C45 | 109.2 (3) |
C22—C21—C23 | 109.3 (3) | N4—C44—C46 | 115.8 (3) |
N2—C21—H21 | 109.4 | C45—C44—C46 | 110.9 (3) |
C22—C21—H21 | 109.4 | N4—C44—H44 | 106.8 |
C23—C21—H21 | 109.4 | C45—C44—H44 | 106.8 |
C21—C22—H22A | 109.5 | C46—C44—H44 | 106.8 |
C21—C22—H22B | 109.5 | C44—C45—H45A | 109.5 |
H22A—C22—H22B | 109.5 | C44—C45—H45B | 109.5 |
C21—C22—H22C | 109.5 | H45A—C45—H45B | 109.5 |
H22A—C22—H22C | 109.5 | C44—C45—H45C | 109.5 |
H22B—C22—H22C | 109.5 | H45A—C45—H45C | 109.5 |
C21—C23—H23A | 109.5 | H45B—C45—H45C | 109.5 |
C21—C23—H23B | 109.5 | C44—C46—H46A | 109.5 |
H23A—C23—H23B | 109.5 | C44—C46—H46B | 109.5 |
C21—C23—H23C | 109.5 | H46A—C46—H46B | 109.5 |
H23A—C23—H23C | 109.5 | C44—C46—H46C | 109.5 |
H23B—C23—H23C | 109.5 | H46A—C46—H46C | 109.5 |
N2—C24—C26 | 115.6 (3) | H46B—C46—H46C | 109.5 |
N2—C24—C25 | 109.3 (3) |
Experimental details
Crystal data | |
Chemical formula | [Be2(C6H14NO)4] |
Mr | 482.75 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 110 |
a, b, c (Å) | 8.2156 (17), 13.248 (3), 14.317 (3) |
α, β, γ (°) | 98.82 (2), 97.42 (2), 102.42 (2) |
V (Å3) | 1482.5 (5) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.07 |
Crystal size (mm) | 0.20 × 0.10 × 0.05 |
Data collection | |
Diffractometer | Stoe IPDS diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 20278, 5220, 2359 |
Rint | 0.162 |
(sin θ/λ)max (Å−1) | 0.612 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.061, 0.169, 0.98 |
No. of reflections | 5220 |
No. of parameters | 323 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.17, −0.22 |
Computer programs: X-AREA (Stoe & Cie, 2012), X-RED32 (Stoe & Cie, 2012), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009), publCIF (Westrip, 2010).
Acknowledgements
Professor Nicola Hüsing is thanked for generous support.
References
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A large number of coordination compounds of organo-substituted hydoxylamines with electropositive elements M is known up to date (Ullrich, 2007). Depending on the tendency of M to form ionic, covalent, or coordinative bonds to O and N atoms of the hydroxyl amine moiety, and also depending on the valency and the size of M, a comparably large variety of structure motifs and compositions is found. N,N-diisopropylhydoxylamine is probably the sterically most hindered hydroxylamine which is accessible. In continuation of our studies on Be coordination compounds (Berger, Hartmann et al., 2001; Berger et al., 2011; Berger, Schmidt et al., 2001; Dressel et al., 2003; Neumüller & Dehnicke, 2010), it was of special interest to investigate the reaction products formed from Be2+ and deprotonated N,N-diisopopylhydoxylamine.
In the dinuclear unit of the title compound, Be2(C3H7NO)4, the Be2+ cations are bonded to O atoms and one N atom of the hydroxylamine moieties. The mononuclear subunit Be(ONiPr2)2 is connected via an additional Be—O bond to an identical subunit. In addition, a Be—N bond to one of the four hydroxylamine moieties is observed. In this way, each of the two Be2+ cations attains a threefold coordination. (Fig. 1) Such a coordination number is rarely found in Be-containing compounds and usually only in sterically demanding environments. Another striking feature of the molecular arrangement of the title compound is the planarity of the central Be—O—Be—O—N five-membered ring. This is underlined by the sum of 540.0° of the internal angles in the ring and a r.m.s. deviation from planarity of only 0.0087 Å. Despite the planarity, no crystallographically imposed symmetry is found in the molecular unit of Be2(C3H7NO)4.