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1 metal-organic compounds Acta Crystallographica Section E Structure Reports Online ISSN Di-l-bromido-bis[benzyl(diethyl ether)- magnesium] Mark A. Nesbit, Danielle L. Gray and Gregory S. Girolami* University of Illinois at Urbana-Champaign, School of Chemical Sciences, 600 South Mathews Avenue, Urbana, Illinois 61801, USA Correspondence girolami@scs.illinois.edu Received 1 June 2012; accepted 5 June 2012 Key indicators: single-crystal X-ray study; T = 193 K; mean (C C) = Å; R factor = 0.031; wr factor = 0.073; data-to-parameter ratio = Experimental Crystal data [Mg 2 Br 2 (C 7 H 7 ) 2 (C 4 H 10 O) 2 ] M r = Monoclinic, P2 1 =c a = (4) Å b = (6) Å c = (6) Å = (3) Data collection Bruker Platform APEXII CCD diffractometer Absorption correction: integration (SADABS; Bruker, 2007) T min = 0.440, T max = Refinement R[F 2 >2(F 2 )] = wr(f 2 ) = S = reflections V = (11) Å 3 Z =2 Mo K radiation = 3.15 mm 1 T = 193 K mm measured reflections 2396 independent reflections 1808 reflections with I > 2(I) R int = parameters H-atom parameters not refined max = 0.42 e Å 3 min = 0.36 e Å 3 The title benzyl Grignard reagent, [Mg 2 Br 2 (C 7 H 7 ) 2 - (C 4 H 10 O) 2 ], was obtained by reaction of benzyl bromide with magnesium in diethyl ether, followed by crystallization from toluene. The asymmetric unit comprises one half-molecule, the structural dimeric unit being generated by inversion symmetry with an MgMg distance of (2) Å. The Mg(II) atom exhibits a distorted tetrahedral coordination geometry. The crystal packing is defined by van der Waals interactions only. Related literature For the structures of some other diethyl ether adducts of Grignard reagents, see: Stucky & Rundle (1964); Guggenberger & Rundle (1968); Engelhardt et al. (1988); Antolini et al. (2003); Avent et al. (2004). For the structures of some tetrahydrofuran and diisopropyl ether adducts of Grignard reagents, see: Maurice (1969); Spek et al. (1974); Krieck et al. (2009). Table 1 Selected bond lengths (Å). Mg1 O (18) Mg1 C (3) Symmetry code: (i) x þ 2; y þ 1; z. Mg1 Br1 i (9) Mg1 Br (9) Data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT and XPREP (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: XCIF (Bruker, 2005). This work was supported financially by the National Science Foundation (CHE ). X-ray data were collected in the Materials Chemistry Laboratory at the University of Illinois (supported in part by grants NSF CHE and NSF CHE from the National Science Foundation). Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: KP2423). References Antolini, F., Hitchcock, P. B., Lappert, M. F. & Wei, X.-H. (2003). Organometallics, 22, Avent, A. G., Caro, C. F., Hitchcock, P. B., Lappert, M. F., Li, Z. & Wei, X.-H. (2004). Dalton Trans. pp Bruker (2005). SAINT, XCIF and XPREP. Bruker AXS, Inc., Madison, Wisconsin, USA. Bruker (2007). SADABS. Bruker AXS, Inc., Madison, Wisconsin, USA. Bruker (2010). APEX2. Bruker AXS, Inc., Madison, Wisconsin, USA. Engelhardt, L. M., Harvey, S., Raston, C. L. & White, A. H. (1988). J. Organomet. Chem. 341, Guggenberger, L. J. & Rundle, R. E. (1968). J. Am. Chem. Soc. 90, Krieck, S., Görls, H., Yu, L., Reiher, M. & Westerhausen, M. (2009). J. Am. Chem. Soc. 131, Maurice, V. J. (1969). J. Organomet. Chem. 20, Sheldrick, G. M. (2008). Acta Cryst. A64, Spek, A. L., Voorbergen, P., Schat, G., Blomberg, C. & Bickelhaupt, F. J. (1974). J. Organomet. Chem. 77, Stucky, G. & Rundle, R. E. (1964). J. Am. Chem. Soc. 86, m942 Nesbit et al. doi: /s
2 supplementary materials [doi: /s ] Di-µ-bromido-bis[benzyl(diethyl ether)magnesium] Mark A. Nesbit, Danielle L. Gray and Gregory S. Girolami Comment Similar dimeric structures have been reported for the bromo Grignard reagents [Mg(µ-Br){CH(SiMe 2 Ph)(SiMe 3 )} (OEt 2 )] 2 (Antolini, et al., 2003), [Mg(µ-Br){CH(SiMe 3 ) 2 }(OEt 2 )] 2 (Avent, et al., 2004), and [Mg(µ-Br)Et(O-i-Pr 2 )] 2 (Spek, et al., 1974). In all three of these molecules, the magnesium centres each bear one ether ligand, and two Mg Br Mg bridges join the metal centres. Most bromo Grignard reagents with two ether molecule per Mg centre are monomeric; examples include MgBrPh(OEt 2 ) 2 (Stucky & Rundle, 1964), MgBrEt(OEt 2 ) 2 (Guggenberger & Rundle, 1968), MgBr(CPh 3 )(OEt 2 ) 2 (Engelhardt et al., 1988) and MgBr(2,4,6-C 6 H 2 Ph 3 )(thf) 2 (Krieck et al., 2009). Finally, there are some monomeric bromo Grignard reagents in which the magnesium centre bears three ether ligands and very small organic groups, such as in MgBrMe(thf) 3 (Maurice, 1969). Experimental A 250 ml round bottom flask was charged with Mg turnings (2.6 g, 107 mmol) and diethyl ether (90 ml). To the stirred suspension was added benzyl bromide (10 ml, 84 mmol) dropwise by means of an addition funnel over 30 min. After the slight exotherm had subsided, the solution was brought to reflux for two h. The solution was filtered and the filtrate was stored at 253 K. Titration with 0.13 M HCl showed the solution to have a concentration of 0.93 M. An aliquot of the benzyl magnesium bromide solution (11.5 ml, 10.7 mmol) was taken to dryness under reduced pressure at 263 K and the residue was extracted with 1:1 benzene/toluene (50 ml). The clear yellow extract was concentrated to ca 20 ml and stored at 253 K overnight affording large colourless crystals. Refinement A structural dimeric model of (I) is [Mg(µ-Br)(CH 2 Ph)(OEt 2 )] 2 whereas an asymmetric unit comprises a half of the molecule. All non-h atoms were located from the difference map and refined anisotropically. H atom treatment: methyl H atom positions, R CH 3, were optimised by rotation about R C bonds with idealised C H, R H and H H distances; the remaining H atoms were included as riding idealised contributors. Methyl H atom U's were assigned as 1.5 times U eq of the carrier atom; remaining H atom U's were assigned as 1.2 times carrier U eq. Computing details Data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT and XPREP (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: XCIF (Bruker, 2005). sup-1
3 Figure 1 Structural unit of (I) with 50% probability displacement ellipsoids for non-h atoms. Arbitrary radii for H atoms are used. The unlabeled atoms are related by the symmetry operator (-x + 2, -y + 1, -z). Di-μ-bromido-bis[benzyl(diethyl ether)magnesium] Crystal data [Mg 2 Br 2 (C 7 H 7 ) 2 (C 4 H 10 O) 2 ] M r = Monoclinic, P2 1 /c Hall symbol: -P 2ybc a = (4) Å b = (6) Å c = (6) Å β = (3) V = (11) Å 3 Z = 2 Data collection Bruker Platform APEXII CCD diffractometer Radiation source: normal-focus sealed tube Graphite monochromator profile data from φ and ω scans F(000) = 552 D x = Mg m 3 Mo Kα radiation, λ = Å Cell parameters from 5006 reflections θ = µ = 3.15 mm 1 T = 193 K Prism, colourless mm Absorption correction: integration (SADABS; Bruker, 2007) T min = 0.440, T max = measured reflections 2396 independent reflections sup-2
4 1808 reflections with I > 2σ(I) R int = θ max = 25.3, θ min = 2.3 Refinement Refinement on F 2 Least-squares matrix: full R[F 2 > 2σ(F 2 )] = wr(f 2 ) = S = reflections 129 parameters 0 restraints Primary atom site location: structure-invariant direct methods h = 9 9 k = l = Secondary atom site location: difference Fourier map Hydrogen site location: inferred from neighbouring sites H-atom parameters not refined w = 1/[σ 2 (F o2 ) + (0.0305P) P] where P = (F o 2 + 2F c2 )/3 (Δ/σ) max = Δρ max = 0.42 e Å 3 Δρ min = 0.36 e Å 3 Special details Experimental. One distinct cell was identified using APEX2 (Bruker, 2010). Ten frame series were integrated and filtered for statistical outliers using SAINT (Bruker, 2005) then corrected for absorption by integration using SHELXTL/XPREP V2005/2 (Bruker, 2005) before using SADABS (Bruker, 2005) to sort, merge, and scale the combined data. No decay correction was applied. 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. The structure was phased by direct methods (Sheldrick, 2008). The systematic conditions suggested the unambiguous space group. The space group choice was confirmed by successful convergence of the full-matrix leastsquares refinement on F 2. The highest peaks in the final difference Fourier map were in the vicinity of atom Br1; the final map had no other significant features. A final analysis of variance between observed and calculated structure factors showed little dependence on amplitude or resolution. Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 ) x y z U iso */U eq Mg (11) (7) (7) (2) Br (3) (2) (2) (13) O (2) (13) (14) (5) C (3) (2) (2) (7) C (4) (2) (2) (8) H * C (4) (3) (3) (10) H * C (4) (3) (3) (10) H * C (4) (2) (3) (9) H * C (3) (2) (2) (7) H * C (3) (19) (2) (7) H7A * H7B * C (4) (2) (2) (8) sup-3
5 H8A * H8B * C (4) (2) (2) (10) H9A * H9B * H9C * C (4) (2) (2) (8) H10A * H10B * C (4) (3) (2) (10) H11A * H11B * H11C * Atomic displacement parameters (Å 2 ) U 11 U 22 U 33 U 12 U 13 U 23 Mg (5) (5) (6) (4) (4) (4) Br (2) (2) (2) (14) (14) (14) O (11) (10) (12) (8) (9) (9) C (16) (16) (18) (12) (13) (13) C (19) (19) (2) (15) (16) (15) C (2) (2) (2) (18) (19) (18) C (2) (2) (3) (17) (2) (2) C (2) (19) (3) (16) (19) (18) C (18) (18) (19) (14) (15) (14) C (17) (16) (2) (13) (14) (13) C (18) (17) (2) (15) (16) (15) C (3) (19) (2) (19) (2) (16) C (19) (18) (2) (14) (17) (15) C (3) (3) (2) (2) (2) (19) Geometric parameters (Å, º) Mg1 O (18) C5 C (4) Mg1 C (3) C5 H Mg1 Br1 i (9) C6 H Mg1 Br (9) C7 H7A Mg1 Mg1 i (17) C7 H7B Br1 Mg1 i (9) C8 C (4) O1 C (3) C8 H8A O1 C (3) C8 H8B C1 C (4) C9 H9A C1 C (3) C9 H9B C1 C (3) C9 H9C C2 C (4) C10 C (4) C2 H C10 H10A C3 C (4) C10 H10B C3 H C11 H11A C4 C (4) C11 H11B sup-4
6 C4 H C11 H11C O1 Mg1 C (9) C1 C6 H O1 Mg1 Br1 i (6) C1 C7 Mg (17) C7 Mg1 Br1 i (9) C1 C7 H7A O1 Mg1 Br (6) Mg1 C7 H7A C7 Mg1 Br (8) C1 C7 H7B Br1 i Mg1 Br (3) Mg1 C7 H7B O1 Mg1 Mg1 i (6) H7A C7 H7B C7 Mg1 Mg1 i (8) O1 C8 C (3) Br1 i Mg1 Mg1 i (2) O1 C8 H8A Br1 Mg1 Mg1 i (2) C9 C8 H8A Mg1 i Br1 Mg (3) O1 C8 H8B C8 O1 C (2) C9 C8 H8B C8 O1 Mg (16) H8A C8 H8B C10 O1 Mg (15) C8 C9 H9A C2 C1 C (3) C8 C9 H9B C2 C1 C (3) H9A C9 H9B C6 C1 C (3) C8 C9 H9C C3 C2 C (3) H9A C9 H9C C3 C2 H H9B C9 H9C C1 C2 H O1 C10 C (2) C4 C3 C (3) O1 C10 H10A C4 C3 H C11 C10 H10A C2 C3 H O1 C10 H10B C3 C4 C (3) C11 C10 H10B C3 C4 H H10A C10 H10B C5 C4 H C10 C11 H11A C4 C5 C (3) C10 C11 H11B C4 C5 H H11A C11 H11B C6 C5 H C10 C11 H11C C5 C6 C (3) H11A C11 H11C C5 C6 H H11B C11 H11C Symmetry code: (i) x+2, y+1, z. sup-5
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