2. Experimental Crystal data
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1 data reports ISSN Crystal structure of (tert-butyldimethylsilyl)triphenylgermane, Ph 3 Ge-SiMe 2 (t-bu) Kirill V. Zaitsev, a Galina S. Zaitseva, a Sergey S. Karlov a * and Alexander A. Korlyukov b a Department of Chemistry, M.V. Lomonosov Moscow State University, Leninskie Gory 1/3, Moscow, Russian Federation, and b A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilova St. 28, Moscow, Russian Federation. *Correspondence sergej@org.chem.msu.ru Received 20 November 2015; accepted 30 November Experimental 2.1. Crystal data C 24 H 30 GeSi M r = Monoclinic, C2=c a = (6) Å b = (7) Å c = (13) Å = (10) V = (4) Å 3 Z =8 Mo K radiation = 1.44 mm 1 T = 120 K mm Edited by W. Imhof, University Koblenz-Landau, Germany In the title compound, Ph 3 Ge-SiMe 2 (t-bu) or C 24 H 30 GeSi, the Si and Ge atoms both possess a tetrahedral coordination environment with C E C (E = Si, Ge) angles in the range (5) (5). The molecule adopts an eclipsed conformation, with three torsion angles less than In the crystal, neighbouring molecules are combined to dimers by six T-shaped C H interactions, forming sixfold phenyl embraces (6PE). Keywords: catenated compounds; silagermanes; C H interactions; 6PE interactions; crystal structure. CCDC reference: Related literature For general background to the chemistry of Group 14 element catenated compounds, see: Marschner & Hlina (2013); Amadoruge & Weinert (2008); Párkányi et al. (1986); Leigh et al. (1997). As apart of our studies of the chemistry of oligogermanium compounds (Zaitsev et al. 2012, 2013, 2014a,b), the title compound was obtained and studied. For related crystal structures of silagermanes, see: Zaitsev et al. (2015). The 6PE interactions are intensively discussed in Scudder & Dance (2000); Steiner (2000); Churakov et al. (2005) Data collection Bruker SMART APEXII CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2013) T min = 0.720, T max = Refinement R[F 2 >2(F 2 )] = wr(f 2 ) = S = reflections measured reflections 7990 independent reflections 6137 reflections with I > 2(I) R int = parameters H-atom parameters constrained max = 0.43 e Å 3 min = 0.37 e Å 3 Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT; program(s) used to solve structure: SHELXS2014 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2. Acknowledgements This work was supported financially by the Russian President Grant for Young Russian Scientists (MK ) Supporting information for this paper is available from the IUCr electronic archives (Reference: IM2474). References Amadoruge, M. L. & Weinert, C. S. (2008). Chem. Rev. 108, Bruker (2013). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Churakov, A. V., Prikhodchenko, P. V. & Howard, J. A. K. (2005). CrystEngComm, 7, Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, doi: /s Zaitsev et al. o1015
2 data reports Leigh, W. J., Kroll, E. C., Toltl, N. P. & Britten, J. F. (1997). Acta Cryst. C53, IUC Marschner, C. & Hlina, J. (2013). Comprehensive Inorganic Chemistry II, 2nd ed., edited by J. Reedijk & K. Poeppelmeier, pp Amsterdam: Elsevier. Párkányi, L., Hernandez, C. & Pannell, K. H. (1986). J. Organomet. Chem. 301, Scudder, M. & Dance, I. (2000). J. Chem. Soc. Dalton Trans. pp Sheldrick, G. M. (2008). Acta Cryst. A64, Sheldrick, G. M. (2015). Acta Cryst. C71, 3 8. Steiner, T. (2000). New J. Chem. 24, Zaitsev, K. V., Churakov, A. V., Poleshchuk, O. K., Oprunenko, Yu. F., Zaitseva, G. S. & Karlov, S. S. (2014a). Dalton Trans. 43, Zaitsev, K. V., Kapranov, A. A., Churakov, A. V., Poleshchuk, O. K., Oprunenko, Yu. F., Tarasevich, B. N., Zaitseva, G. S. & Karlov, S. S. (2013). Organometallics, 32, Zaitsev, K. V., Kapranov, A. A., Oprunenko, Y. F., Churakov, A. V., Howard, J. A. K., Tarasevich, B. N., Karlov, S. S. & Zaitseva, G. S. (2012). J. Organomet. Chem. 700, Zaitsev, K. V., Lermontova, E. K., Churakov, A. V., Tafeenko, V. A., Tarasevich, B. N., Poleshchuk, O. K., Kharcheva, A. V., Magdesieva, T. V., Nikitin, O. M., Zaitseva, G. S. & Karlov, S. S. (2015). Organometallics, 34, Zaitsev, K. V., Oprunenko, Y. F., Churakov, A. V., Zaitseva, G. S. & Karlov, S. S. (2014b). Main Group Met. Chem. 37, o1016 Zaitsev et al. C 24 H 30 GeSi
3 supporting information [ Crystal structure of (tert-butyldimethylsilyl)triphenylgermane, Ph 3 Ge-SiMe 2 (t- Bu) Kirill V. Zaitsev, Galina S. Zaitseva, Sergey S. Karlov and Alexander A. Korlyukov S1. Structural commentary In the title compound, Ph 3 Ge-SiMe 2 (t-bu), both Si and Ge atoms possess tetrahedral coordination environments with C E C angles ranging within (5) (5). The Ge Si bond length ( (4) Å) is slightly longer than in the closely related compound Ph 3 Ge-SiMe 3 (2.384 (1) Å (Párkányi et al., 1986). The molecule adopts an eclipsed conformation with three torsion angles less than In the crystal, neighbouring molecules are combined to dimers by six T-shaped C H π interactions forming six-fold phenyl embraces (6PE, Steiner, 2000; Churakov et al., 2005). As expected for 6PE-bonded molecules, the C ax Ge Ge angle is almost linear (Fig. 2; Scudder & Dance, 2000). The title compound is isostructural with the corresponding silicon complex Ph 3 Si-SiMe 2 (t-bu) (Leigh et al., 1997). S2. Synthesis and crystallization The synthetic procedure leading to the title compound was reported by us earlier (Zaitsev et al., 2014b) to give a white crystalline material in good yield (86 %) by the reaction of Ph 3 GeLi (generated in situ from equimolar amounts of Ph 3 GeH and n-buli at room temperature in Et 2 O) with t-bume 2 SiCl in diethyl ether. Solvent-free crystals of the title compound suitable for X-Ray analysis were obtained after recrystallization from n-hexane at room temperature. S3. Refinement Crystal data, data collection and structure refinement details are summarized in Table 1. All non-hydrogen atoms were refined with anisotropic thermal parameters. All hydrogen atoms were placed in calculated positions and refined using a riding model, with C H = Å, and with U iso (H) = 1.2 U eq (C) for aromatic hydrogens or 1.5 U eq (C) for methyl H atoms. A rotating model was applied to the methyl groups. sup-1
4 Figure 1 Molecular structure of the title compound, with displacement ellipsoids shown at the 50% probability level. sup-2
5 Figure 2 Dimers formed by 6PE interactions between adjacent molecules. (tert-butyldimethylsilyl)triphenylgermane Crystal data C 24 H 30 GeSi M r = Monoclinic, C2/c a = (6) Å b = (7) Å c = (13) Å β = (10) V = (4) Å 3 Z = 8 Data collection Bruker SMART APEXII CCD area-detector diffractometer Radiation source: sealed tube Graphite monochromator Detector resolution: 8 pixels mm -1 ω and φ scans Absorption correction: multi-scan (SADABS; Bruker, 2013) T min = 0.720, T max = Refinement Refinement on F 2 Least-squares matrix: full R[F 2 > 2σ(F 2 )] = wr(f 2 ) = S = reflections 240 parameters 0 restraints F(000) = 1760 D x = Mg m 3 Mo Kα radiation, λ = Å Cell parameters from 8565 reflections θ = µ = 1.44 mm 1 T = 120 K Irregular, colourless mm measured reflections 7990 independent reflections 6137 reflections with I > 2σ(I) R int = θ max = 32.6, θ min = 1.9 h = k = l = Hydrogen site location: inferred from neighbouring sites H-atom parameters constrained w = 1/[σ 2 (F o2 ) + (0.0303P) P] where P = (F o 2 + 2F c2 )/3 (Δ/σ) max = Δρ max = 0.43 e Å 3 Δρ min = 0.37 e Å 3 sup-3
6 Special details Experimental. Absorption correctgion: SADABS-2008/1 (Bruker,2008) was used for absorption correction. wr2(int) was before and after correction. The Ratio of minimum to maximum transmission is The λ/2 correction factor is 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. Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 ) x y z U iso */U eq Ge (2) (2) (2) (4) Si (3) (3) (2) (8) C (11) (9) (7) (3) C (13) (11) (8) (3) H2A * H2B * H2C * C (13) (12) (8) (4) H3A * H3B * H3C * C (13) (11) (8) (4) H4A * H4B * H4C * C (12) (11) (8) (4) H5A * H5B * H5C * C (14) (13) (8) (4) H6A * H6B * H6C * C (10) (9) (6) (3) C (12) (10) (7) (3) H * C (13) (11) (8) (4) H * C (12) (11) (7) (3) H * C (11) (11) (7) (3) H * C (11) (10) (6) (3) H * C (11) (9) (6) (3) C (11) (10) (7) (3) sup-4
7 H * C (12) (11) (7) (3) H * C (12) (11) (7) (3) H * C (12) (11) (7) (3) H * C (11) (10) (7) (3) H * C (10) (9) (6) (3) C (11) (10) (7) (3) H * C (12) (10) (7) (3) H * C (12) (10) (7) (3) H * C (12) (10) (7) (3) H * C (11) (10) (7) (3) H * Atomic displacement parameters (Å 2 ) U 11 U 22 U 33 U 12 U 13 U 23 Ge (7) (7) (7) (6) (5) (6) Si (18) (18) (18) (14) (14) (14) C (6) (7) (7) (5) (5) (5) C (8) (8) (8) (7) (7) (7) C (8) (9) (8) (7) (6) (7) C (8) (8) (9) (7) (7) (7) C (8) (8) (9) (7) (7) (7) C (10) (10) (8) (8) (7) (7) C (6) (6) (6) (5) (5) (5) C (7) (7) (8) (6) (6) (6) C (8) (7) (9) (6) (7) (7) C (7) (8) (7) (6) (6) (6) C (6) (8) (7) (6) (5) (6) C (7) (7) (6) (5) (5) (5) C (6) (6) (6) (5) (5) (5) C (7) (7) (7) (6) (6) (6) C (7) (9) (8) (6) (6) (6) C (8) (9) (7) (7) (6) (6) C (8) (8) (7) (6) (6) (6) C (7) (7) (7) (6) (6) (6) C (6) (6) (6) (5) (5) (5) C (7) (7) (7) (5) (5) (6) C (7) (7) (8) (6) (6) (6) C (8) (6) (8) (6) (6) (6) sup-5
8 C (8) (7) (8) (6) (6) (6) C (7) (7) (7) (6) (5) (6) Geometric parameters (Å, º) Ge1 Si (4) C9 H Ge1 C (14) C9 C (2) Ge1 C (14) C10 H Ge1 C (13) C10 C (2) Si1 C (15) C11 H Si1 C (15) C11 C (2) Si1 C (17) C12 H C1 C (2) C13 C (2) C1 C (2) C13 C (2) C1 C (2) C14 H C2 H2A C14 C (2) C2 H2B C15 H C2 H2C C15 C (2) C3 H3A C16 H C3 H3B C16 C (2) C3 H3C C17 H C4 H4A C17 C (2) C4 H4B C18 H C4 H4C C19 C (19) C5 H5A C19 C (2) C5 H5B C20 H C5 H5C C20 C (2) C6 H6A C21 H C6 H6B C21 C (2) C6 H6C C22 H C7 C (2) C22 C (2) C7 C (19) C23 H C8 H C23 C (2) C8 C (2) C24 H C7 Ge1 Si (4) C7 C8 H C7 Ge1 C (6) C9 C8 C (15) C13 Ge1 Si (4) C9 C8 H C19 Ge1 Si (4) C8 C9 H C19 Ge1 C (6) C10 C9 C (15) C19 Ge1 C (6) C10 C9 H C1 Si1 Ge (5) C9 C10 H C5 Si1 Ge (5) C11 C10 C (14) C5 Si1 C (7) C11 C10 H C6 Si1 Ge (6) C10 C11 H C6 Si1 C (7) C10 C11 C (14) C6 Si1 C (9) C12 C11 H C2 C1 Si (10) C7 C12 H sup-6
9 C2 C1 C (13) C11 C12 C (14) C3 C1 Si (10) C11 C12 H C3 C1 C (13) C14 C13 Ge (10) C3 C1 C (13) C14 C13 C (13) C4 C1 Si (10) C18 C13 Ge (11) C1 C2 H2A C13 C14 H C1 C2 H2B C15 C14 C (14) C1 C2 H2C C15 C14 H H2A C2 H2B C14 C15 H H2A C2 H2C C16 C15 C (15) H2B C2 H2C C16 C15 H C1 C3 H3A C15 C16 H C1 C3 H3B C17 C16 C (14) C1 C3 H3C C17 C16 H H3A C3 H3B C16 C17 H H3A C3 H3C C16 C17 C (14) H3B C3 H3C C18 C17 H C1 C4 H4A C13 C18 H C1 C4 H4B C17 C18 C (14) C1 C4 H4C C17 C18 H H4A C4 H4B C20 C19 Ge (10) H4A C4 H4C C24 C19 Ge (10) H4B C4 H4C C24 C19 C (13) Si1 C5 H5A C19 C20 H Si1 C5 H5B C21 C20 C (14) Si1 C5 H5C C21 C20 H H5A C5 H5B C20 C21 H H5A C5 H5C C20 C21 C (14) H5B C5 H5C C22 C21 H Si1 C6 H6A C21 C22 H Si1 C6 H6B C23 C22 C (14) Si1 C6 H6C C23 C22 H H6A C6 H6B C22 C23 H H6A C6 H6C C22 C23 C (14) H6B C6 H6C C24 C23 H C8 C7 Ge (11) C19 C24 C (14) C12 C7 Ge (11) C19 C24 H C12 C7 C (13) C23 C24 H Ge1 C7 C8 C (13) C13 C14 C15 C (2) Ge1 C7 C12 C (11) C14 C13 C18 C (2) Ge1 C13 C14 C (12) C14 C15 C16 C (3) Ge1 C13 C18 C (12) C15 C16 C17 C (2) Ge1 C19 C20 C (11) C16 C17 C18 C (2) Ge1 C19 C24 C (11) C18 C13 C14 C (2) C7 C8 C9 C (3) C19 C20 C21 C (2) C8 C7 C12 C (2) C20 C19 C24 C (2) C8 C9 C10 C (2) C20 C21 C22 C (2) sup-7
10 C9 C10 C11 C (2) C21 C22 C23 C (2) C10 C11 C12 C7 0.4 (2) C22 C23 C24 C (2) C12 C7 C8 C9 0.2 (2) C24 C19 C20 C (2) sup-8
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organic compounds Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 Redetermination and absolute configuration of 6-hydroxysalvinolone Hoong-Kun Fun, a * Ching Kheng Quah a and Suchada
More informationExperimental. Crystal data. C 23 H 34 O 4 M r = Orthorhombic, P a = (6) Å b = (4) Å c = 18.
organic compounds Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 3b-Acetoxy-19-hydroxy-D 5 -pregnen-20- one Aike Meier zu Greffen, Darius P. Kranz, Jörg-M. Neudörfl and Hans-Günther
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metal-organic compounds Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 (E)-1-Ferrocenyl-3-(3-nitrophenyl)prop- 2-en-1-one Yong-Hong Liu,* Jun Ye, Xiao-Lan Liu, Wen-Long Liu and
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metal-organic compounds Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 Diaqua[(1R,2S,4R,8R,9S,11R)-2,9-dimethyl-1,4,8,11-tetraazacyclotetradecane]nickel(II) dichloride dihydrate
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organic compounds Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 3-(Adamantan-1-yl)-4-[(E)-(2,6-difluoro- benzylidene)amino]-1-[(4-ethylpiperazin- 1-yl)methyl]-4,5-dihydro-1H-1,2,4-triazole-5-thione
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metal-organic compounds Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 Dichlorido(4,4 0 -di-tert-butyl-2,2 0 -bipyridine-j 2 N,N 0 )palladium(ii) dimethyl sulfoxide monosolvate
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organic compounds Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 (2Z)-2-(4-Methylphenyl)-3-(2-naphthyl)- prop-2-enenitrile Abdullah Mohamed Asiri, a Mehmet Akkurt, b * Islam Ullah
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organic compounds Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 (E)-N-[2-(Benzyliminomethyl)phenyl]- 2,6-diisopropylaniline Yi-Chang Liu, a Chia-Her Lin, a Hsiao-Li Chen b and
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organic compounds Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 N,N 0,N 00 -Triphenylguanidinium 5-nitro- 2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1- ide P. S. Pereira Silva, S.
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organic compounds Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 3b-Chloro-6-[2-(2-cyanoacetyl)hydrazin- 1-ylidene]-5a-cholestane Samina Khan Yusufzai, a Hasnah Osman, a Aisyah
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organic compounds Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 N-(2,4,5-Trichlorophenyl)maleamic acid B. Thimme Gowda, a * Miroslav Tokarčík, b Jozef Kožíšek, b K. Shakuntala
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metal-organic compounds Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 b = 19.1695 (15) Å c = 16.6178 (14) Å = 90.786 (6) V = 2077.4 (3) Å 3 Z =4 Mo K radiation = 1.34 mm 1 T
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organic compounds Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 4-Nitrophenyl a-l-rhamnopyranoside hemihydrate 1 Jianbo Zhang, a * Jie Fu, a Xuan Chen, a Yijun Gu b and Jie Tang
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