Z. Kristallogr. NCS 2019; aop Kimberleigh B. Govender, Marivel Samipillai, Thavendran Govender, Hendrik G. Kruger and Tricia Naicker* Crystal structure of 2-(bis(3,5-dimethylphenyl) ((methyldiphenylsilyl)oxy)methyl) pyrrolidine, C 34 H 39 NOSi https://doi.org/10.1515/ncrs-2018-0422 Received October 11, 2018; accepted December 29, 2018; available online January 12, 2019 Abstract C 34 H 39 NOSi, triclinic, P ¯ 1 (no. 2), a = 10.0901(2) Å, b = 11.5016(2) Å, c = 14.4098(3) Å, α = 69.207(1)°, β = 86.555(2)°, γ = 65.579(3)°, V = 1416.10(6) Å 3 , Z = 2, R gt (F) = 0.0463, wR ref (F 2 ) = 0.1200, T = 100(2) K. CCDC no.: 1887917 The crystal structure is shown in the figure. Tables 1 and 2 con- tain details on crystal structure and measurement conditions *Corresponding author: Tricia Naicker, University of KwaZulu Natal, Catalysis and Peptide Research Unit, Durban 4000, South Africa, e-mail: naickert1@ukzn.ac.za Kimberleigh B. Govender, Marivel Samipillai, Thavendran Govender and Hendrik G. Kruger: University of KwaZulu Natal, Catalysis and Peptide Research Unit, Durban 4000, South Africa Table 1: Data collection and handling. Crystal: Colourless block Size: 0.37 × 0.24 × 0.13 mm Wavelength: Mo Kα radiation (0.71073 Å) μ: 0.11 mm -1 Difractometer, scan mode: Bruker APEX-II CCD, φ and ω θ max , completeness: 28.8°, 99% N(hkl) measured , N(hkl) unique , R int : 39154, 7216, 0.020 Criterion for I obs , N(hkl) gt : I obs > 2 σ(I obs ), 6613 N(param) refned : 382 Programs: COSMO [1], Bruker [2, 3], Olex2 [4], ORTEP-3 [5], SHELX [6, 7] and a list of the atoms including atomic coordinates and displacement parameters. Source of material A mixture of (R)-α,α-bis(3,5-dimethylphenyl)-2- pyrrolidinemethanol (100 mg, 1.0 eq), DIEA (2.0 eq) and DMAP (0.2 eq) was stirred in anhydrous DCM (1.6 mL) at room temperature. Chloro(methyl)diphenylsilane (1.2 eq) was added and the reaction mixture was refluxed for 24 h. The reaction was quenched with water and the resulting mix- ture was extracted twice with DCM. The combined organic layers were then washed once with brine, dried with Na 2 SO 4 and concentrated. The crude material was then purified by column chromatography (20% EtOAc/n-hexane, R f = 0.2) to yield the title compound as an off-white solid (yield 56.2 mg, 34.4%). The product was dissolved in acetonitrile after the addition of heat and subsequent evaporation yielded colour- less crystals suitable for X-ray analysis. m.p. 106 - 108 °C. 1 H-NMR (CDCl 3 , 400 MHz) : δ [ppm] 0.25 (3H, s), 0.92 – 0.98 (1H, m), 1.17 – 1.21 (1H, m), 1.47 – 1.53 (2H, m), 1.66 – 1.73 (1H, m), 2.25 (12H, s), 2.60 – 2.65 (1H, m), 2.77 – 2.81 (1H, m), 3.99 – 4.02 (1H, t, J = 4.52 Hz), 6.86 – 6.89 (2H, d, J = 11.8 Hz), 6.99 (2H, s), 7.10 (2H, s), 7.32 – 7.37 (6H, m), 7.54 (4H, s). Experimental details All hydrogen atoms attached to carbon were placed in ide- alised positions and refined using the riding model with Open Access. © 2019 Kimberleigh B. Govender et al., published by De Gruyter. This work is licensed under the Creative Commons Attribution- NonCommercial-NoDerivatives 4.0 License.