# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2001 # CCDC Number: 148999 database_code_CSD 148999 Perkin Transactions 1 James C. Anderson and Alice Flaherty . Table 1. Crystal data and structure refinement for BTCSIM at 150(2)K. Empirical formula C21 H34 N2 O3 Si Formula weight 390.59 Crystal description Colourless Block Crystal size 0.41 x 0.26 x 0.14 mm Crystal system Monoclinic Space group P2(1)/c Unit cell dimensions a = 10.0044(6) A alpha = 90 deg. b = 21.5554(13) A beta = 91.963(1) deg. c = 10.6645(7) A gamma = 90 deg. Volume 2298.4(2) A^3 Reflections for cell refinement 4042 Range in theta 2.24 to 28.72 deg. Z 4 Density (calculated) 1.129 Mg/m^3 Absorption coefficient 0.123 mm^-1 F(000) 848 Diffractometer type Bruker CCD area detector Wavelength 0.71073 A Scan type omega Reflections collected 12413 Theta range for data collection 1.89 to 28.73 deg. Index ranges -5<=h<=13, -28<=k<=25, -13<=l<=14 Independent reflections 5315 [R(int) = 0.0370] Observed reflections 3738 [I>2sigma(I)] Decay correction none Structure solution by direct and difference Fourier methods Hydrogen atom location difference Fourier Hydrogen atom treatment Me riding model, others refined Data / restraints / parameters 5315/0/284 (least-squares on F^2) Final R indices [I>2sigma(I)] R1 = 0.0407, wR2 = 0.1045 Final R indices (all data) R1 = 0.0637, wR2 = 0.1140 Goodness-of-fit on F^2 0.995 Final maximum delta/sigma 0.001 Weighting scheme calc w=1/[\s^2^(Fo^2^)+(0.0628P)^2^] where P=(Fo^2^+2Fc^2^)/3 Largest diff. peak and hole 0.273 and -0.233 e.A^-3 Table 2. Atomic coordinates ( x 10^4) and equivalent isotropic displacement parameters (A^2 x 10^3) for BTCSIM. U(eq) is defined as one third of the trace of the orthogonalized Uij tensor. ________________________________________________________________ x y z U(eq) ________________________________________________________________ Si 744(1) 5912(1) 8342(1) 32(1) O1 6253(1) 5259(1) 8534(1) 33(1) N1 5616(1) 5590(1) 6600(1) 29(1) C1 5349(2) 5408(1) 7774(1) 26(1) N2 3586(1) 4811(1) 8756(1) 25(1) O2 3430(1) 4348(1) 6856(1) 35(1) C2 3899(2) 5407(1) 8188(1) 24(1) O3 3298(1) 3787(1) 8662(1) 29(1) C3 3684(1) 5932(1) 9136(1) 25(1) C4 2223(2) 5996(1) 9482(1) 27(1) C5 1976(2) 6101(1) 10687(2) 36(1) C6 1071(2) 6241(1) 6744(2) 36(1) C7 1055(2) 5876(1) 5662(2) 45(1) C8 1291(2) 6121(1) 4486(2) 57(1) C9 1557(3) 6743(1) 4362(2) 64(1) C10 1565(3) 7118(1) 5398(2) 66(1) C11 1321(2) 6871(1) 6570(2) 53(1) C12 301(2) 5075(1) 8164(2) 42(1) C13 -683(2) 6353(1) 8985(2) 51(1) C14 4210(2) 6552(1) 8635(2) 35(1) C15 7011(2) 5640(1) 6255(2) 40(1) C16 4609(2) 5756(1) 5635(2) 42(1) C17 3442(2) 4316(1) 7998(1) 26(1) C18 3146(2) 3192(1) 7994(2) 33(1) C19 4378(2) 3064(1) 7245(2) 55(1) C20 1859(2) 3193(1) 7194(2) 56(1) C21 3053(2) 2726(1) 9051(2) 46(1) ________________________________________________________________ Table 5. Hydrogen coordinates ( x 10^4) and isotropic displacement parameters (A^2 x 10^3) for BTCSIM. ________________________________________________________________ x y z U(eq) ________________________________________________________________ H2A 3631(16) 4780(8) 9527(17) 37(5) H2 3306(14) 5457(6) 7492(13) 18(3) H3 4226(15) 5819(7) 9894(14) 26(4) H5A 2734(17) 6125(8) 11330(16) 36(4) H5B 1087(18) 6177(8) 10980(17) 50(5) H7 854(18) 5431(9) 5742(17) 50(5) H8 1310(20) 5856(10) 3790(20) 66(6) H9 1740(20) 6904(10) 3540(20) 78(7) H10 1740(20) 7546(11) 5320(20) 78(7) H11 1340(20) 7138(10) 7288(19) 63(6) H12A 949 4871 7632 63 H12B -597 5038 7774 63 H12C 318 4877 8991 63 H13A -1450 6334 8390 76 H13B -420 6786 9117 76 H13C -928 6170 9786 76 H14A 5177 6523 8532 52 H14B 4021 6884 9231 52 H14C 3766 6644 7822 52 H15A 7107 5483 5400 60 H15B 7575 5396 6839 60 H15C 7289 6076 6293 60 H16A 4982 5701 4804 62 H16B 4347 6190 5743 62 H16C 3824 5489 5710 62 H19A 4375 2629 6977 82 H19B 5183 3145 7769 82 H19C 4374 3334 6506 82 H20A 1691 2776 6861 84 H20B 1944 3486 6497 84 H20C 1113 3319 7709 84 H18A 2976 2307 8701 70 H18B 2264 2818 9539 70 H18C 3858 2753 9598 70 ________________________________________________________________ Table 3. Bond lengths [A], angles [deg] for BTCSIM. _____________________________________________________________ Si-C4 1.8915(16) Si-C6 1.8843(18) Si-C12 1.8668(16) Si-C13 1.8643(18) O1-C1 1.2359(17) N1-C1 1.3468(18) N1-C15 1.460(2) N1-C16 1.4598(19) C1-C2 1.531(2) N2-C2 1.4588(17) N2-C17 1.3435(17) N2-H2A 0.825(18) O2-C17 1.2191(17) C2-C3 1.5384(19) C2-H2 0.940(14) O3-C17 1.3520(16) O3-C18 1.4729(16) C3-C4 1.525(2) C3-C14 1.539(2) C3-H3 0.988(15) C4-C5 1.336(2) C5-H5A 1.007(17) C5-H5B 0.967(18) C6-C11 1.394(2) C6-C7 1.395(2) C7-C8 1.389(3) C7-H7 0.985(19) C8-C9 1.373(3) C8-H8 0.94(2) C9-C10 1.369(3) C9-H9 0.97(2) C10-C11 1.389(3) C10-H10 0.94(2) C11-H11 0.96(2) C12-H12A 0.9800 C12-H12B 0.9800 C12-H12C 0.9800 C13-H13A 0.9800 C13-H13B 0.9800 C13-H13C 0.9800 C14-H14A 0.9800 C14-H14B 0.9800 C14-H14C 0.9800 C15-H15A 0.9800 C15-H15B 0.9800 C15-H15C 0.9800 C16-H16A 0.9800 C16-H16B 0.9800 C16-H16C 0.9800 C18-C21 1.515(2) C18-C19 1.517(2) C18-C20 1.520(2) C19-H19A 0.9800 C19-H19B 0.9800 C19-H19C 0.9800 C20-H20A 0.9800 C20-H20B 0.9800 C20-H20C 0.9800 C21-H18A 0.9800 C21-H18B 0.9800 C21-H18C 0.9800 C13-Si-C12 110.36(9) C13-Si-C6 107.50(8) C12-Si-C6 108.61(8) C13-Si-C4 107.88(8) C12-Si-C4 109.58(7) C6-Si-C4 112.89(7) C1-N1-C16 124.98(13) C1-N1-C15 118.53(13) C16-N1-C15 116.48(12) O1-C1-N1 121.42(14) O1-C1-C2 119.33(12) N1-C1-C2 119.22(12) C17-N2-C2 117.98(12) C17-N2-H2A 122.5(12) C2-N2-H2A 118.7(12) N2-C2-C1 109.93(11) N2-C2-C3 109.75(12) C1-C2-C3 110.04(11) N2-C2-H2 107.0(8) C1-C2-H2 110.5(8) C3-C2-H2 109.5(8) C17-O3-C18 119.44(11) C4-C3-C2 112.47(12) C4-C3-C14 110.31(12) C2-C3-C14 110.71(12) C4-C3-H3 109.2(9) C2-C3-H3 105.8(8) C14-C3-H3 108.2(9) C5-C4-C3 117.26(14) C5-C4-Si 117.88(13) C3-C4-Si 124.83(10) C4-C5-H5A 120.3(10) C4-C5-H5B 122.8(11) H5A-C5-H5B 116.8(14) C11-C6-C7 115.86(17) C11-C6-Si 121.55(14) C7-C6-Si 122.58(13) C8-C7-C6 122.32(18) C8-C7-H7 119.3(11) C6-C7-H7 118.3(11) C9-C8-C7 119.8(2) C9-C8-H8 120.5(13) C7-C8-H8 119.5(13) C10-C9-C8 119.7(2) C10-C9-H9 121.7(14) C8-C9-H9 118.6(14) C9-C10-C11 120.2(2) C9-C10-H10 119.9(14) C11-C10-H10 119.9(14) C10-C11-C6 122.1(2) C10-C11-H11 119.2(12) C6-C11-H11 118.6(13) Si-C12-H12A 109.5 Si-C12-H12B 109.5 H12A-C12-H12B 109.5 Si-C12-H12C 109.5 H12A-C12-H12C 109.5 H12B-C12-H12C 109.5 Si-C13-H13A 109.5 Si-C13-H13B 109.5 H13A-C13-H13B 109.5 Si-C13-H13C 109.5 H13A-C13-H13C 109.5 H13B-C13-H13C 109.5 C3-C14-H14A 109.5 C3-C14-H14B 109.5 H14A-C14-H14B 109.5 C3-C14-H14C 109.5 H14A-C14-H14C 109.5 H14B-C14-H14C 109.5 N1-C15-H15A 109.5 N1-C15-H15B 109.5 H15A-C15-H15B 109.5 N1-C15-H15C 109.5 H15A-C15-H15C 109.5 H15B-C15-H15C 109.5 N1-C16-H16A 109.5 N1-C16-H16B 109.5 H16A-C16-H16B 109.5 N1-C16-H16C 109.5 H16A-C16-H16C 109.5 H16B-C16-H16C 109.5 O2-C17-N2 123.56(13) O2-C17-O3 125.03(13) N2-C17-O3 111.40(12) O3-C18-C21 102.99(12) O3-C18-C19 109.97(13) C21-C18-C19 110.06(14) O3-C18-C20 109.94(13) C21-C18-C20 110.26(15) C19-C18-C20 113.14(15) C18-C19-H19A 109.5 C18-C19-H19B 109.5 H19A-C19-H19B 109.5 C18-C19-H19C 109.5 H19A-C19-H19C 109.5 H19B-C19-H19C 109.5 C18-C20-H20A 109.5 C18-C20-H20B 109.5 H20A-C20-H20B 109.5 C18-C20-H20C 109.5 H20A-C20-H20C 109.5 H20B-C20-H20C 109.5 C18-C21-H18A 109.5 C18-C21-H18B 109.5 H18A-C21-H18B 109.5 C18-C21-H18C 109.5 H18A-C21-H18C 109.5 H18B-C21-H18C 109.5 _____________________________________________________________ Table 4. Anisotropic displacement parameters (A^2 x 10^3) for BTCSIM. The anisotropic displacement factor exponent takes the form: -2 pi^2 [ h^2 a*^2 U11 + ... + 2 h k a* b* U12 ] _______________________________________________________________________ U11 U22 U33 U23 U13 U12 _______________________________________________________________________ Si 30(1) 27(1) 40(1) -5(1) -2(1) 1(1) O1 33(1) 42(1) 22(1) 5(1) -1(1) 6(1) N1 31(1) 37(1) 20(1) 5(1) 1(1) 1(1) C1 34(1) 22(1) 22(1) -1(1) 0(1) 2(1) N2 37(1) 21(1) 16(1) 1(1) 1(1) 0(1) O2 57(1) 29(1) 19(1) -1(1) 2(1) -2(1) C2 31(1) 22(1) 19(1) 2(1) -2(1) 1(1) O3 46(1) 21(1) 22(1) -1(1) 3(1) -1(1) C3 30(1) 23(1) 23(1) -1(1) -2(1) 0(1) C4 32(1) 17(1) 31(1) 0(1) 3(1) -1(1) C5 37(1) 37(1) 35(1) -2(1) 6(1) -3(1) C6 36(1) 31(1) 41(1) 0(1) -12(1) 4(1) C7 54(1) 38(1) 41(1) 0(1) -13(1) -2(1) C8 74(2) 59(1) 38(1) 0(1) -17(1) 3(1) C9 82(2) 65(1) 46(1) 21(1) -16(1) 3(1) C10 90(2) 38(1) 69(2) 18(1) -14(1) 2(1) C11 72(1) 35(1) 52(1) 0(1) -13(1) 6(1) C12 38(1) 35(1) 53(1) -4(1) -4(1) -8(1) C13 35(1) 54(1) 63(1) -15(1) -3(1) 9(1) C14 38(1) 25(1) 42(1) -2(1) 5(1) -5(1) C15 35(1) 57(1) 27(1) 3(1) 3(1) -4(1) C16 41(1) 61(1) 23(1) 12(1) 0(1) 6(1) C17 31(1) 23(1) 23(1) 0(1) 3(1) 2(1) C18 49(1) 20(1) 30(1) -6(1) 3(1) -1(1) C19 74(1) 35(1) 58(1) -6(1) 25(1) 10(1) C20 69(1) 39(1) 58(1) -5(1) -17(1) -13(1) C21 72(1) 23(1) 45(1) 1(1) 5(1) -3(1) _______________________________________________________________________