Supplementary Material (ESI) for Organic and Biomolecular Chemistry This journal is (C) The Royal Society of Chemistry 2006 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Matthias Tamm' _publ_contact_author_address ; Institut fur Anorganische und Analytische Chemie Technische Universitat Braunschweig Hagenring 30 Braunschweig 38106 GERMANY ; _publ_contact_author_email MATTHIAS.TAMM@TU-BS.DE #============================================================================== # 3. TITLE AND AUTHOR LIST _publ_section_title ; Structural and Theoretical Investigation of 2-Iminoimidazolines Carbene Analogues of Iminophosphoranes ; loop_ _publ_author_name _publ_author_address M.Tamm ; Institut fur Anorganische und Analytische Chemie, Technische Universitat Braunschweig, Hagenring 30, D-38106 Braunschweig, Germany ; D.Petrovic ; Institut fur Anorganische und Analytische Chemie, Technische Universitat Braunschweig, Hagenring 30, D-38106 Braunschweig, Germany ; S.Randoll ; Institut fur Anorganische und Analytische Chemie, Technische Universitat Braunschweig, Hagenring 30, D-38106 Braunschweig, Germany ; S.Beer ; Institut fur Anorganische und Analytische Chemie, Technische Universitat Braunschweig, Hagenring 30, D-38106 Braunschweig, Germany ; T.Bannenberg ; Institut fur Anorganische und Analytische Chemie Technische Universitat Braunschweig Hagenring 30, 38106 Braunschweig Germany ; P.G.Jones ; Institut fur Anorganische und Analytische Chemie Technische Universitat Braunschweig Hagenring 30, 38106 Braunschweig Germany ; ; J.Grunenberg ; ; Institut fur Organische Chemie Technische Universitat Braunschweig Hagenring 30, 38106 Braunschweig Germany ; #============================================================================= # cif data for "sran1" (compound 2d in manuscript) #============================================================================= data_sran1 _database_code_depnum_ccdc_archive 'CCDC 618030' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety 'C24 H33 N3 Si' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C24 H33 N3 Si' _chemical_formula_weight 391.62 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,-y,-z _cell_length_a 8.47290(10) _cell_length_b 8.93460(10) _cell_length_c 15.8498(3) _cell_angle_alpha 88.5376(6) _cell_angle_beta 80.8585(6) _cell_angle_gamma 83.8057(6) _cell_volume 1177.66(3) _cell_formula_units_Z 2 _cell_measurement_temperature 173 _cell_measurement_reflns_used 4222 _cell_measurement_theta_min 1.30 _cell_measurement_theta_max 25.34 _exptl_crystal_description fragment _exptl_crystal_colour yellow _exptl_crystal_size_max 0.400 _exptl_crystal_size_mid 0.350 _exptl_crystal_size_min 0.350 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.104 _exptl_crystal_density_method none _exptl_crystal_F_000 424 _exptl_absorpt_coefficient_mu 0.113 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.956 _exptl_absorpt_correction_T_max 0.961 _exptl_special_details ; ? ; _diffrn_ambient_temperature 173 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'NONIUS FR 591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device ' \k-geometry diffractometer ' _diffrn_measurement_device_type ' Nonius \k-CCD diffractometer' _diffrn_measurement_method ' phi- and omega-rotation ' _diffrn_detector ' CCD plate ' _diffrn_detector_area_resol_mean 18 # 9 for binned mode _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 8419 _diffrn_reflns_av_R_equivalents 0.0162 _diffrn_reflns_av_sigmaI/netI 0.0224 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.30 _diffrn_reflns_theta_max 25.34 _reflns_number_total 4282 _reflns_number_gt 3809 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Kappa-CCD Control Software (Nonius, 2001a)' _computing_cell_refinement 'DENZO (Nonius, 2001b)' _computing_data_reduction 'DENZO (Nonius, 2001b)' _computing_structure_solution 'SIR92 (Altomare, 1994)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1998)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'PLATON (Spek, 2003)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme sigma _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(Fo^2^)+(0.0534P)^2^+0.4222P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_number_reflns 4282 _refine_ls_number_parameters 385 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0426 _refine_ls_R_factor_gt 0.0374 _refine_ls_wR_factor_ref 0.1039 _refine_ls_wR_factor_gt 0.1003 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags Si Si Uani 0.49675(5) 0.44925(4) 0.31373(2) 1.000 0.0278(1) . . N1 N Uani 0.47139(16) 0.34191(14) 0.23190(8) 1.000 0.0349(4) . . N2 N Uani 0.43622(15) 0.17298(14) 0.12587(7) 1.000 0.0315(4) . . N3 N Uani 0.28892(15) 0.14831(14) 0.25075(8) 1.000 0.0321(4) . . C1 C Uani 0.40506(16) 0.23349(16) 0.20779(8) 1.000 0.0274(4) . . C2 C Uani 0.3420(2) 0.05634(19) 0.12026(10) 1.000 0.0403(5) . . C3 C Uani 0.2528(2) 0.0408(2) 0.19603(11) 1.000 0.0435(6) . . C4 C Uani 0.55911(18) 0.21688(17) 0.05984(9) 1.000 0.0309(4) . . C5 C Uani 0.71974(19) 0.17738(18) 0.06833(9) 1.000 0.0350(4) . . C6 C Uani 0.8377(2) 0.2202(2) 0.00336(10) 1.000 0.0413(5) . . C7 C Uani 0.7988(2) 0.2988(2) -0.06840(10) 1.000 0.0427(5) . . C8 C Uani 0.6384(2) 0.33450(19) -0.07494(10) 1.000 0.0409(5) . . C9 C Uani 0.51537(19) 0.29457(17) -0.01172(9) 1.000 0.0348(4) . . C10 C Uani 0.7666(2) 0.0896(3) 0.14475(12) 1.000 0.0487(6) . . C11 C Uani 0.9300(3) 0.3459(4) -0.13704(16) 1.000 0.0657(9) . . C12 C Uani 0.3422(2) 0.3321(2) -0.02249(13) 1.000 0.0471(6) . . C13 C Uani 0.23705(17) 0.14822(16) 0.34131(9) 1.000 0.0290(4) . . C14 C Uani 0.10157(17) 0.24221(17) 0.37598(9) 1.000 0.0328(4) . . C15 C Uani 0.05235(18) 0.23623(19) 0.46400(10) 1.000 0.0369(5) . . C16 C Uani 0.13201(18) 0.13804(18) 0.51640(9) 1.000 0.0341(5) . . C17 C Uani 0.26520(18) 0.04443(17) 0.47885(10) 1.000 0.0341(5) . . C18 C Uani 0.32061(17) 0.04852(16) 0.39188(9) 1.000 0.0311(4) . . C19 C Uani 0.0098(2) 0.3441(3) 0.31961(13) 1.000 0.0498(6) . . C20 C Uani 0.0742(3) 0.1315(3) 0.61121(11) 1.000 0.0476(6) . . C21 C Uani 0.4679(2) -0.0500(2) 0.35248(13) 1.000 0.0441(6) . . C22 C Uani 0.6527(2) 0.57494(18) 0.26938(11) 1.000 0.0355(5) . . C23 C Uani 0.5680(3) 0.3384(2) 0.40459(11) 1.000 0.0452(6) . . C24 C Uani 0.3124(2) 0.5734(2) 0.35877(13) 1.000 0.0473(6) . . H21 H Uiso 0.346(2) 0.006(2) 0.0690(12) 1.000 0.047(5) . . H31 H Uiso 0.175(2) -0.026(2) 0.2159(13) 1.000 0.056(6) . . H61 H Uiso 0.950(2) 0.195(2) 0.0091(12) 1.000 0.052(5) . . H81 H Uiso 0.612(2) 0.388(2) -0.1231(12) 1.000 0.045(5) . . H101 H Uiso 0.744(2) 0.154(2) 0.1945(14) 1.000 0.058(6) . . H102 H Uiso 0.880(3) 0.056(3) 0.1376(15) 1.000 0.076(7) . . H103 H Uiso 0.699(3) 0.005(3) 0.1595(15) 1.000 0.082(8) . . H111 H Uiso 0.972(4) 0.433(4) -0.121(2) 1.000 0.126(12) . . H112 H Uiso 0.897(4) 0.363(4) -0.187(2) 1.000 0.125(12) . . H113 H Uiso 1.028(5) 0.286(5) -0.139(2) 1.000 0.158(16) . . H121 H Uiso 0.272(2) 0.348(2) 0.0310(14) 1.000 0.057(6) . . H122 H Uiso 0.301(3) 0.247(3) -0.0470(14) 1.000 0.069(6) . . H123 H Uiso 0.330(3) 0.417(3) -0.0612(15) 1.000 0.068(6) . . H151 H Uiso -0.037(2) 0.300(2) 0.4878(11) 1.000 0.044(5) . . H171 H Uiso 0.322(2) -0.026(2) 0.5133(11) 1.000 0.043(5) . . H191 H Uiso 0.082(3) 0.395(3) 0.2768(17) 1.000 0.090(8) . . H192 H Uiso -0.056(3) 0.420(3) 0.3539(16) 1.000 0.082(8) . . H193 H Uiso -0.051(3) 0.286(3) 0.2891(16) 1.000 0.080(7) . . H201 H Uiso 0.096(4) 0.211(4) 0.638(2) 1.000 0.114(11) . . H202 H Uiso 0.127(4) 0.049(4) 0.639(2) 1.000 0.140(13) . . H203 H Uiso -0.033(4) 0.114(3) 0.6225(16) 1.000 0.091(8) . . H211 H Uiso 0.553(3) 0.013(2) 0.3273(13) 1.000 0.060(6) . . H212 H Uiso 0.444(2) -0.106(2) 0.3068(14) 1.000 0.056(6) . . H213 H Uiso 0.507(3) -0.119(2) 0.3964(14) 1.000 0.063(6) . . H221 H Uiso 0.744(2) 0.516(2) 0.2366(13) 1.000 0.053(5) . . H222 H Uiso 0.691(2) 0.627(2) 0.3162(13) 1.000 0.059(6) . . H223 H Uiso 0.612(2) 0.651(2) 0.2287(12) 1.000 0.052(5) . . H231 H Uiso 0.656(3) 0.262(3) 0.3856(15) 1.000 0.077(7) . . H232 H Uiso 0.480(3) 0.289(3) 0.4361(15) 1.000 0.072(7) . . H233 H Uiso 0.609(2) 0.403(2) 0.4433(13) 1.000 0.062(6) . . H241 H Uiso 0.273(3) 0.634(3) 0.3129(16) 1.000 0.079(7) . . H242 H Uiso 0.340(2) 0.642(2) 0.3982(13) 1.000 0.058(6) . . H243 H Uiso 0.227(3) 0.517(3) 0.3887(15) 1.000 0.074(7) . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Si 0.0307(2) 0.0290(2) 0.0239(2) -0.0039(2) -0.0023(2) -0.0057(2) N1 0.0444(7) 0.0369(7) 0.0243(6) -0.0045(5) 0.0000(5) -0.0154(6) N2 0.0351(7) 0.0363(7) 0.0237(6) -0.0060(5) -0.0004(5) -0.0112(5) N3 0.0334(7) 0.0382(7) 0.0257(6) -0.0035(5) -0.0006(5) -0.0130(5) C1 0.0283(7) 0.0312(7) 0.0222(7) -0.0012(6) -0.0023(5) -0.0035(6) C2 0.0471(9) 0.0453(9) 0.0316(8) -0.0120(7) -0.0050(7) -0.0173(7) C3 0.0479(10) 0.0498(10) 0.0363(9) -0.0086(7) -0.0021(7) -0.0257(8) C4 0.0360(8) 0.0338(8) 0.0228(7) -0.0072(6) 0.0001(6) -0.0082(6) C5 0.0380(8) 0.0398(8) 0.0271(7) -0.0043(6) -0.0037(6) -0.0053(7) C6 0.0343(9) 0.0512(10) 0.0377(9) -0.0036(7) -0.0017(7) -0.0067(7) C7 0.0453(9) 0.0485(10) 0.0330(8) -0.0010(7) 0.0036(7) -0.0134(8) C8 0.0534(10) 0.0426(9) 0.0269(8) 0.0025(7) -0.0052(7) -0.0083(8) C9 0.0396(8) 0.0370(8) 0.0279(7) -0.0062(6) -0.0043(6) -0.0050(7) C10 0.0445(10) 0.0630(12) 0.0373(10) 0.0047(9) -0.0083(8) 0.0014(9) C11 0.0577(14) 0.0871(18) 0.0494(13) 0.0144(12) 0.0083(10) -0.0232(13) C12 0.0442(10) 0.0557(12) 0.0427(10) -0.0030(9) -0.0119(8) -0.0025(8) C13 0.0286(7) 0.0324(8) 0.0267(7) -0.0007(6) -0.0010(6) -0.0112(6) C14 0.0278(7) 0.0377(8) 0.0330(8) 0.0018(6) -0.0027(6) -0.0072(6) C15 0.0278(8) 0.0432(9) 0.0370(9) -0.0031(7) 0.0036(6) -0.0035(7) C16 0.0321(8) 0.0418(9) 0.0287(8) 0.0004(6) 0.0009(6) -0.0141(6) C17 0.0360(8) 0.0335(8) 0.0342(8) 0.0049(7) -0.0062(7) -0.0097(6) C18 0.0302(7) 0.0289(7) 0.0344(8) -0.0024(6) -0.0023(6) -0.0072(6) C19 0.0405(10) 0.0601(12) 0.0474(11) 0.0070(9) -0.0097(8) 0.0034(9) C20 0.0460(10) 0.0661(13) 0.0304(9) 0.0005(9) 0.0033(7) -0.0188(9) C21 0.0436(10) 0.0386(9) 0.0474(10) -0.0077(8) -0.0037(8) 0.0046(8) C22 0.0361(8) 0.0327(8) 0.0384(9) -0.0006(7) -0.0050(7) -0.0079(7) C23 0.0575(11) 0.0468(10) 0.0354(9) 0.0059(8) -0.0135(8) -0.0157(9) C24 0.0396(9) 0.0495(11) 0.0502(11) -0.0167(9) 0.0023(8) -0.0033(8) _geom_special_details ; 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. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag Si N1 1.6866(13) . . yes Si C22 1.8671(17) . . yes Si C23 1.8691(19) . . yes Si C24 1.8687(18) . . yes N1 C1 1.2668(19) . . yes N2 C1 1.3943(17) . . yes N2 C2 1.392(2) . . yes N2 C4 1.4333(19) . . yes N3 C1 1.3905(19) . . yes N3 C3 1.400(2) . . yes N3 C13 1.4328(19) . . yes C2 C3 1.326(2) . . no C4 C5 1.395(2) . . no C4 C9 1.394(2) . . no C5 C6 1.393(2) . . no C5 C10 1.509(3) . . no C6 C7 1.387(2) . . no C7 C8 1.382(2) . . no C7 C11 1.513(3) . . no C8 C9 1.396(2) . . no C9 C12 1.505(2) . . no C13 C14 1.393(2) . . no C13 C18 1.395(2) . . no C14 C15 1.393(2) . . no C14 C19 1.503(3) . . no C15 C16 1.389(2) . . no C16 C17 1.391(2) . . no C16 C20 1.506(2) . . no C17 C18 1.385(2) . . no C18 C21 1.505(2) . . no C2 H21 0.933(18) . . no C3 H31 0.948(18) . . no C6 H61 0.972(17) . . no C8 H81 0.935(18) . . no C10 H101 0.97(2) . . no C10 H102 0.97(3) . . no C10 H103 1.00(3) . . no C11 H111 0.95(4) . . no C11 H112 0.89(3) . . no C11 H113 0.94(4) . . no C12 H121 0.96(2) . . no C12 H122 0.98(3) . . no C12 H123 0.97(3) . . no C15 H151 0.931(18) . . no C17 H171 0.963(18) . . no C19 H191 0.98(3) . . no C19 H192 0.95(3) . . no C19 H193 0.96(3) . . no C20 H201 0.89(4) . . no C20 H202 0.96(3) . . no C20 H203 0.93(3) . . no C21 H211 0.99(2) . . no C21 H212 0.95(2) . . no C21 H213 0.99(2) . . no C22 H221 0.972(18) . . no C22 H222 1.000(19) . . no C22 H223 0.997(18) . . no C23 H231 0.97(3) . . no C23 H232 0.97(3) . . no C23 H233 0.979(19) . . no C24 H241 0.98(3) . . no C24 H242 0.958(19) . . no C24 H243 0.98(3) . . no loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Si C22 106.23(7) . . . yes N1 Si C23 113.62(7) . . . yes N1 Si C24 113.86(8) . . . yes C22 Si C23 108.39(9) . . . yes C22 Si C24 107.11(8) . . . yes C23 Si C24 107.33(9) . . . yes Si N1 C1 147.22(11) . . . yes C1 N2 C2 110.56(12) . . . yes C1 N2 C4 123.91(12) . . . yes C2 N2 C4 125.29(12) . . . yes C1 N3 C3 110.18(12) . . . yes C1 N3 C13 125.14(12) . . . yes C3 N3 C13 123.56(13) . . . yes N1 C1 N2 125.03(13) . . . yes N1 C1 N3 131.56(13) . . . yes N2 C1 N3 103.40(12) . . . yes N2 C2 C3 107.82(14) . . . yes N3 C3 C2 108.04(15) . . . yes N2 C4 C5 118.77(13) . . . yes N2 C4 C9 119.37(14) . . . yes C5 C4 C9 121.85(14) . . . no C4 C5 C6 118.05(14) . . . no C4 C5 C10 121.71(14) . . . no C6 C5 C10 120.24(15) . . . no C5 C6 C7 121.73(16) . . . no C6 C7 C8 118.53(15) . . . no C6 C7 C11 120.34(17) . . . no C8 C7 C11 121.12(17) . . . no C7 C8 C9 122.12(15) . . . no C4 C9 C8 117.71(15) . . . no C4 C9 C12 121.90(14) . . . no C8 C9 C12 120.38(14) . . . no N3 C13 C14 119.52(13) . . . yes N3 C13 C18 118.55(13) . . . yes C14 C13 C18 121.87(13) . . . no C13 C14 C15 117.90(14) . . . no C13 C14 C19 120.80(14) . . . no C15 C14 C19 121.29(14) . . . no C14 C15 C16 121.90(14) . . . no C15 C16 C17 118.24(14) . . . no C15 C16 C20 120.84(16) . . . no C17 C16 C20 120.91(16) . . . no C16 C17 C18 121.94(14) . . . no C13 C18 C17 118.13(13) . . . no C13 C18 C21 120.48(14) . . . no C17 C18 C21 121.38(14) . . . no N2 C2 H21 121.3(11) . . . no C3 C2 H21 130.9(11) . . . no N3 C3 H31 120.4(12) . . . no C2 C3 H31 131.6(12) . . . no C5 C6 H61 118.8(11) . . . no C7 C6 H61 119.5(11) . . . no C7 C8 H81 118.6(11) . . . no C9 C8 H81 119.3(11) . . . no C5 C10 H101 109.3(11) . . . no C5 C10 H102 112.5(14) . . . no C5 C10 H103 111.1(14) . . . no H101 C10 H102 106.4(18) . . . no H101 C10 H103 105.1(18) . . . no H102 C10 H103 112(2) . . . no C7 C11 H111 111.3(19) . . . no C7 C11 H112 113(2) . . . no C7 C11 H113 114(2) . . . no H111 C11 H112 109(3) . . . no H111 C11 H113 93(3) . . . no H112 C11 H113 115(3) . . . no C9 C12 H121 112.7(11) . . . no C9 C12 H122 111.1(15) . . . no C9 C12 H123 111.0(15) . . . no H121 C12 H122 103.1(17) . . . no H121 C12 H123 111.6(18) . . . no H122 C12 H123 107(2) . . . no C14 C15 H151 118.4(11) . . . no C16 C15 H151 119.7(11) . . . no C16 C17 H171 120.3(10) . . . no C18 C17 H171 117.8(10) . . . no C14 C19 H191 111.5(15) . . . no C14 C19 H192 108.9(15) . . . no C14 C19 H193 109.7(16) . . . no H191 C19 H192 107(2) . . . no H191 C19 H193 107(2) . . . no H192 C19 H193 113(2) . . . no C16 C20 H201 112(2) . . . no C16 C20 H202 113.2(19) . . . no C16 C20 H203 111.0(16) . . . no H201 C20 H202 103(3) . . . no H201 C20 H203 114(3) . . . no H202 C20 H203 103(3) . . . no C18 C21 H211 110.0(12) . . . no C18 C21 H212 110.2(11) . . . no C18 C21 H213 109.8(13) . . . no H211 C21 H212 106.4(17) . . . no H211 C21 H213 110.2(19) . . . no H212 C21 H213 110.2(16) . . . no Si C22 H221 109.8(11) . . . no Si C22 H222 111.0(11) . . . no Si C22 H223 111.7(10) . . . no H221 C22 H222 108.7(15) . . . no H221 C22 H223 105.8(16) . . . no H222 C22 H223 109.7(15) . . . no Si C23 H231 112.5(14) . . . no Si C23 H232 109.5(15) . . . no Si C23 H233 111.3(11) . . . no H231 C23 H232 108(2) . . . no H231 C23 H233 105.7(18) . . . no H232 C23 H233 109.4(18) . . . no Si C24 H241 109.3(15) . . . no Si C24 H242 109.1(10) . . . no Si C24 H243 112.9(16) . . . no H241 C24 H242 106.9(19) . . . no H241 C24 H243 110(2) . . . no H242 C24 H243 108.5(18) . . . no _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.241 _refine_diff_density_min -0.300 _refine_diff_density_rms 0.036 #============================================================================= # end of cif data for "sran1" (compound 2d in manuscript) #============================================================================= #============================================================================= # cif data for "sran9x" (compound 2e in manuscript) #============================================================================= data_sran9x _database_code_depnum_ccdc_archive 'CCDC 618031' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety 'C30 H45 N3 Si' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C30 H45 N3 Si' _chemical_formula_weight 475.78 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,-y,-z _cell_length_a 9.6170(8) _cell_length_b 12.4620(10) _cell_length_c 25.214(2) _cell_angle_alpha 88.322(2) _cell_angle_beta 84.261(2) _cell_angle_gamma 79.785(2) _cell_volume 2958.8(4) _cell_formula_units_Z 4 _cell_measurement_temperature 133 _cell_measurement_reflns_used 7606 _cell_measurement_theta_min 2.34 _cell_measurement_theta_max 30.68 _exptl_crystal_description fragment _exptl_crystal_colour yellow _exptl_crystal_size_max 0.400 _exptl_crystal_size_mid 0.350 _exptl_crystal_size_min 0.300 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.068 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1040 _exptl_absorpt_coefficient_mu 0.100 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 133(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1000 CCD area detector' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean 8.192 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 20896 _diffrn_reflns_av_R_equivalents 0.0575 _diffrn_reflns_av_sigmaI/netI 0.1100 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 1.62 _diffrn_reflns_theta_max 28.28 _reflns_number_total 14394 _reflns_number_gt 7844 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'PLATON (Spek, 2003)' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating R_factor_obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(Fo^2^)+(0.0535P)^2^+3.7145P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment 'rigid methyls, other riding' _refine_ls_extinction_method none _refine_ls_number_reflns 14394 _refine_ls_number_parameters 635 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1118 _refine_ls_R_factor_gt 0.0552 _refine_ls_wR_factor_ref 0.1269 _refine_ls_wR_factor_gt 0.1109 _refine_ls_goodness_of_fit_ref 0.895 _refine_ls_restrained_S_all 0.895 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags Si1 Si Uani -0.05135(6) 0.30190(4) 0.13441(2) 1.000 0.0264(2) . . N1 N Uani 0.12157(17) 0.30519(12) 0.13659(6) 1.000 0.0261(5) . . N2 N Uani 0.32997(16) 0.18458(12) 0.09679(6) 1.000 0.0226(5) . . N3 N Uani 0.35948(16) 0.33167(12) 0.13640(6) 1.000 0.0222(5) . . C1 C Uani 0.2531(2) 0.27582(15) 0.12408(7) 1.000 0.0209(6) . . C2 C Uani 0.4747(2) 0.18848(16) 0.09179(8) 1.000 0.0307(7) . . C3 C Uani 0.4922(2) 0.27815(16) 0.11616(8) 1.000 0.0301(7) . . C4 C Uani 0.2711(2) 0.09629(14) 0.07755(7) 1.000 0.0225(6) . . C5 C Uani 0.2348(2) 0.01573(15) 0.11397(7) 1.000 0.0253(6) . . C6 C Uani 0.1839(2) -0.07088(15) 0.09342(8) 1.000 0.0313(7) . . C7 C Uani 0.1698(2) -0.07680(16) 0.03973(8) 1.000 0.0346(7) . . C8 C Uani 0.2045(2) 0.00371(16) 0.00493(8) 1.000 0.0316(7) . . C9 C Uani 0.2561(2) 0.09238(15) 0.02302(7) 1.000 0.0247(6) . . C10 C Uani 0.2511(2) 0.02301(17) 0.17327(8) 1.000 0.0331(7) . . C11 C Uani 0.4029(3) -0.0163(2) 0.18513(9) 1.000 0.0651(10) . . C12 C Uani 0.1555(3) -0.0422(2) 0.20827(10) 1.000 0.0619(10) . . C13 C Uani 0.2923(2) 0.18157(16) -0.01582(7) 1.000 0.0299(7) . . C14 C Uani 0.3915(3) 0.13513(19) -0.06343(9) 1.000 0.0520(9) . . C15 C Uani 0.1579(3) 0.2512(2) -0.03372(12) 1.000 0.0766(11) . . C16 C Uani 0.3355(2) 0.43092(15) 0.16662(7) 1.000 0.0235(6) . . C17 C Uani 0.3130(2) 0.42446(17) 0.22210(8) 1.000 0.0318(7) . . C18 C Uani 0.3000(2) 0.52146(18) 0.25013(8) 1.000 0.0393(8) . . C19 C Uani 0.3086(2) 0.61880(18) 0.22386(9) 1.000 0.0392(8) . . C20 C Uani 0.3280(2) 0.62332(17) 0.16915(8) 1.000 0.0347(7) . . C21 C Uani 0.3408(2) 0.52927(16) 0.13890(8) 1.000 0.0280(7) . . C22 C Uani 0.3063(3) 0.31672(18) 0.25132(8) 1.000 0.0434(9) . . C23 C Uani 0.1847(3) 0.3258(3) 0.29555(12) 1.000 0.0882(14) . . C24 C Uani 0.4457(3) 0.2707(2) 0.27319(13) 1.000 0.0793(13) . . C25 C Uani 0.3530(3) 0.53557(18) 0.07852(8) 1.000 0.0425(8) . . C26 C Uani 0.4472(3) 0.6138(2) 0.05485(10) 1.000 0.0587(10) . . C27 C Uani 0.2051(4) 0.5657(3) 0.05996(11) 1.000 0.0930(15) . . C28 C Uani -0.1381(3) 0.3134(2) 0.20395(9) 1.000 0.0483(9) . . C29 C Uani -0.1322(2) 0.42319(18) 0.09588(10) 1.000 0.0460(8) . . C30 C Uani -0.0966(2) 0.17817(17) 0.10427(9) 1.000 0.0401(8) . . Si2 Si Uani 0.47452(6) 0.84619(4) 0.38366(2) 1.000 0.0243(2) . . N4 N Uani 0.63004(17) 0.76404(12) 0.39048(6) 1.000 0.0262(5) . . N5 N Uani 0.83489(17) 0.63585(12) 0.40678(6) 1.000 0.0232(5) . . N6 N Uani 0.86471(17) 0.75635(12) 0.34378(6) 1.000 0.0236(5) . . C31 C Uani 0.7605(2) 0.72503(14) 0.38064(7) 1.000 0.0210(6) . . C32 C Uani 0.9766(2) 0.61585(16) 0.38678(8) 1.000 0.0291(7) . . C33 C Uani 0.9953(2) 0.68944(15) 0.34832(8) 1.000 0.0297(7) . . C34 C Uani 0.7701(2) 0.57100(14) 0.44706(7) 1.000 0.0234(6) . . C35 C Uani 0.7339(2) 0.47331(15) 0.43161(8) 1.000 0.0277(6) . . C36 C Uani 0.6783(2) 0.40905(16) 0.47167(8) 1.000 0.0356(7) . . C37 C Uani 0.6591(2) 0.44155(18) 0.52399(9) 1.000 0.0402(8) . . C38 C Uani 0.6930(2) 0.53943(17) 0.53796(8) 1.000 0.0361(7) . . C39 C Uani 0.7492(2) 0.60736(15) 0.49961(8) 1.000 0.0280(6) . . C40 C Uani 0.7498(2) 0.44118(15) 0.37318(8) 1.000 0.0330(7) . . C41 C Uani 0.7726(3) 0.31801(17) 0.36488(10) 1.000 0.0537(9) . . C42 C Uani 0.6211(3) 0.49683(17) 0.34537(8) 1.000 0.0416(8) . . C43 C Uani 0.7873(2) 0.71531(17) 0.51430(8) 1.000 0.0357(7) . . C44 C Uani 0.9352(3) 0.6969(2) 0.53364(12) 1.000 0.0653(11) . . C45 C Uani 0.6790(3) 0.77863(19) 0.55525(10) 1.000 0.0564(10) . . C46 C Uani 0.8374(2) 0.84659(14) 0.30745(7) 1.000 0.0238(6) . . C47 C Uani 0.7941(2) 0.82773(16) 0.25754(8) 1.000 0.0276(6) . . C48 C Uani 0.7599(2) 0.91804(17) 0.22441(8) 1.000 0.0336(7) . . C49 C Uani 0.7689(2) 1.02192(17) 0.24080(8) 1.000 0.0361(7) . . C50 C Uani 0.8175(2) 1.03729(16) 0.28900(8) 1.000 0.0362(7) . . C51 C Uani 0.8546(2) 0.94926(15) 0.32372(7) 1.000 0.0292(7) . . C52 C Uani 0.7920(3) 0.71260(17) 0.23920(9) 1.000 0.0391(8) . . C53 C Uani 0.6600(3) 0.7026(2) 0.21262(11) 1.000 0.0575(10) . . C54 C Uani 0.9241(3) 0.6717(2) 0.20188(13) 1.000 0.0861(13) . . C55 C Uani 0.9135(3) 0.96479(17) 0.37651(8) 1.000 0.0380(8) . . C56 C Uani 0.7954(3) 1.0115(2) 0.41916(9) 1.000 0.0557(10) . . C57 C Uani 1.0296(2) 1.03394(18) 0.37019(9) 1.000 0.0464(8) . . C58 C Uani 0.3840(3) 0.88080(17) 0.45140(8) 1.000 0.0423(8) . . C59 C Uani 0.4781(2) 0.97811(16) 0.34682(8) 1.000 0.0372(7) . . C60 C Uani 0.3613(2) 0.77174(18) 0.34738(9) 1.000 0.0439(8) . . H2 H Uiso 0.54770 0.13660 0.07420 1.000 0.0370 calc R H3 H Uiso 0.58010 0.30120 0.11910 1.000 0.0360 calc R H6 H Uiso 0.15840 -0.12680 0.11680 1.000 0.0380 calc R H7 H Uiso 0.13590 -0.13700 0.02660 1.000 0.0410 calc R H8 H Uiso 0.19310 -0.00120 -0.03190 1.000 0.0380 calc R H10 H Uiso 0.22420 0.10130 0.18370 1.000 0.0400 calc R H11A H Uiso 0.43020 -0.09390 0.17680 1.000 0.0970 calc R H11B H Uiso 0.41120 -0.00550 0.22290 1.000 0.0970 calc R H11C H Uiso 0.46550 0.02520 0.16330 1.000 0.0970 calc R H12A H Uiso 0.19010 -0.12040 0.20310 1.000 0.0930 calc R H12B H Uiso 0.05810 -0.02360 0.19830 1.000 0.0930 calc R H12C H Uiso 0.15700 -0.02440 0.24580 1.000 0.0930 calc R H13 H Uiso 0.34240 0.23000 0.00350 1.000 0.0360 calc R H14A H Uiso 0.47760 0.09160 -0.05100 1.000 0.0780 calc R H14B H Uiso 0.41690 0.19490 -0.08630 1.000 0.0780 calc R H14C H Uiso 0.34390 0.08880 -0.08370 1.000 0.0780 calc R H15A H Uiso 0.18360 0.30860 -0.05820 1.000 0.1150 calc R H15B H Uiso 0.09860 0.28440 -0.00250 1.000 0.1150 calc R H15C H Uiso 0.10520 0.20530 -0.05200 1.000 0.1150 calc R H18 H Uiso 0.28510 0.52010 0.28790 1.000 0.0470 calc R H19 H Uiso 0.30100 0.68350 0.24380 1.000 0.0470 calc R H20 H Uiso 0.33270 0.69130 0.15170 1.000 0.0420 calc R H22 H Uiso 0.28890 0.26370 0.22480 1.000 0.0520 calc R H23A H Uiso 0.20660 0.36720 0.32520 1.000 0.1320 calc R H23B H Uiso 0.17240 0.25260 0.30820 1.000 0.1320 calc R H23C H Uiso 0.09700 0.36340 0.28180 1.000 0.1320 calc R H24A H Uiso 0.46690 0.32170 0.29880 1.000 0.1190 calc R H24B H Uiso 0.52160 0.25990 0.24390 1.000 0.1190 calc R H24C H Uiso 0.43880 0.20060 0.29100 1.000 0.1190 calc R H25 H Uiso 0.39510 0.46120 0.06490 1.000 0.0510 calc R H26A H Uiso 0.40470 0.68840 0.06550 1.000 0.0880 calc R H26B H Uiso 0.45650 0.60910 0.01590 1.000 0.0880 calc R H26C H Uiso 0.54110 0.59450 0.06790 1.000 0.0880 calc R H27A H Uiso 0.14730 0.51190 0.07390 1.000 0.1400 calc R H27B H Uiso 0.21200 0.56630 0.02090 1.000 0.1400 calc R H27C H Uiso 0.16070 0.63810 0.07320 1.000 0.1400 calc R H28A H Uiso -0.09720 0.25060 0.22510 1.000 0.0720 calc R H28B H Uiso -0.24020 0.31480 0.20360 1.000 0.0720 calc R H28C H Uiso -0.12260 0.38070 0.21970 1.000 0.0720 calc R H29A H Uiso -0.12150 0.48990 0.11350 1.000 0.0690 calc R H29B H Uiso -0.23320 0.42190 0.09420 1.000 0.0690 calc R H29C H Uiso -0.08420 0.42150 0.05970 1.000 0.0690 calc R H30A H Uiso -0.04910 0.16860 0.06800 1.000 0.0600 calc R H30B H Uiso -0.19950 0.18750 0.10300 1.000 0.0600 calc R H30C H Uiso -0.06460 0.11370 0.12600 1.000 0.0600 calc R H32 H Uiso 1.04790 0.55970 0.39840 1.000 0.0350 calc R H33 H Uiso 1.08210 0.69510 0.32780 1.000 0.0360 calc R H36 H Uiso 0.65340 0.34190 0.46270 1.000 0.0430 calc R H37 H Uiso 0.62200 0.39620 0.55080 1.000 0.0480 calc R H38 H Uiso 0.67790 0.56090 0.57420 1.000 0.0430 calc R H40 H Uiso 0.83510 0.46810 0.35550 1.000 0.0400 calc R H41A H Uiso 0.84800 0.28180 0.38600 1.000 0.0810 calc R H41B H Uiso 0.80000 0.30210 0.32710 1.000 0.0810 calc R H41C H Uiso 0.68440 0.29110 0.37620 1.000 0.0810 calc R H42A H Uiso 0.53700 0.46710 0.35970 1.000 0.0620 calc R H42B H Uiso 0.63890 0.48350 0.30700 1.000 0.0620 calc R H42C H Uiso 0.60500 0.57550 0.35170 1.000 0.0620 calc R H43 H Uiso 0.79040 0.76110 0.48110 1.000 0.0430 calc R H44A H Uiso 0.96290 0.76750 0.53900 1.000 0.0980 calc R H44B H Uiso 1.00330 0.65550 0.50700 1.000 0.0980 calc R H44C H Uiso 0.93420 0.65590 0.56740 1.000 0.0980 calc R H45A H Uiso 0.58430 0.78720 0.54280 1.000 0.0840 calc R H45B H Uiso 0.70330 0.85070 0.56000 1.000 0.0840 calc R H45C H Uiso 0.67980 0.73880 0.58930 1.000 0.0840 calc R H48 H Uiso 0.73020 0.90850 0.19030 1.000 0.0400 calc R H49 H Uiso 0.74110 1.08300 0.21840 1.000 0.0430 calc R H50 H Uiso 0.82600 1.10860 0.29890 1.000 0.0430 calc R H52 H Uiso 0.79440 0.66390 0.27150 1.000 0.0470 calc R H53A H Uiso 0.66010 0.74320 0.17870 1.000 0.0860 calc R H53B H Uiso 0.57530 0.73250 0.23600 1.000 0.0860 calc R H53C H Uiso 0.65950 0.62560 0.20590 1.000 0.0860 calc R H54A H Uiso 0.92680 0.59490 0.19380 1.000 0.1290 calc R H54B H Uiso 1.00880 0.67900 0.21910 1.000 0.1290 calc R H54C H Uiso 0.92150 0.71500 0.16880 1.000 0.1290 calc R H55 H Uiso 0.95730 0.89100 0.38930 1.000 0.0460 calc R H56A H Uiso 0.83670 1.02100 0.45230 1.000 0.0840 calc R H56B H Uiso 0.72770 0.96130 0.42550 1.000 0.0840 calc R H56C H Uiso 0.74630 1.08230 0.40700 1.000 0.0840 calc R H57A H Uiso 1.10450 1.00190 0.34310 1.000 0.0700 calc R H57B H Uiso 1.06960 1.03650 0.40430 1.000 0.0700 calc R H57C H Uiso 0.98940 1.10810 0.35910 1.000 0.0700 calc R H58A H Uiso 0.37630 0.81350 0.47170 1.000 0.0630 calc R H58B H Uiso 0.28890 0.92280 0.44820 1.000 0.0630 calc R H58C H Uiso 0.43930 0.92430 0.46990 1.000 0.0630 calc R H59A H Uiso 0.52720 1.02430 0.36650 1.000 0.0560 calc R H59B H Uiso 0.38060 1.01540 0.34340 1.000 0.0560 calc R H59C H Uiso 0.52820 0.96390 0.31130 1.000 0.0560 calc R H60A H Uiso 0.40760 0.75350 0.31160 1.000 0.0660 calc R H60B H Uiso 0.26860 0.81810 0.34450 1.000 0.0660 calc R H60C H Uiso 0.34820 0.70460 0.36700 1.000 0.0660 calc R loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Si1 0.0206(3) 0.0285(3) 0.0300(3) -0.0052(2) -0.0017(2) -0.0041(2) N1 0.0214(9) 0.0280(9) 0.0290(9) -0.0063(7) -0.0024(7) -0.0038(7) N2 0.0213(9) 0.0233(8) 0.0237(8) -0.0061(7) 0.0002(7) -0.0055(7) N3 0.0187(8) 0.0218(8) 0.0264(8) -0.0051(7) 0.0001(7) -0.0053(7) C1 0.0248(11) 0.0227(9) 0.0162(9) -0.0007(7) -0.0015(8) -0.0070(8) C2 0.0196(11) 0.0291(11) 0.0417(12) -0.0097(9) 0.0052(9) -0.0026(9) C3 0.0197(11) 0.0311(11) 0.0402(12) -0.0044(9) 0.0004(9) -0.0077(9) C4 0.0222(10) 0.0196(9) 0.0252(10) -0.0038(8) -0.0024(8) -0.0019(8) C5 0.0217(11) 0.0246(10) 0.0268(10) 0.0000(8) 0.0014(8) 0.0010(8) C6 0.0308(12) 0.0231(11) 0.0403(12) 0.0045(9) -0.0015(10) -0.0076(9) C7 0.0375(13) 0.0249(11) 0.0447(13) -0.0048(10) -0.0100(10) -0.0106(10) C8 0.0393(13) 0.0287(11) 0.0287(11) -0.0052(9) -0.0085(10) -0.0071(10) C9 0.0271(11) 0.0218(10) 0.0245(10) -0.0028(8) 0.0000(9) -0.0030(8) C10 0.0417(14) 0.0296(11) 0.0256(11) 0.0006(9) 0.0021(10) -0.0032(10) C11 0.0463(17) 0.115(2) 0.0308(13) -0.0021(14) -0.0119(12) -0.0008(16) C12 0.0614(19) 0.083(2) 0.0405(15) 0.0108(14) 0.0048(13) -0.0176(16) C13 0.0420(13) 0.0263(11) 0.0218(10) -0.0023(8) -0.0001(9) -0.0088(10) C14 0.0677(19) 0.0443(14) 0.0408(14) -0.0014(11) 0.0170(13) -0.0131(13) C15 0.0562(19) 0.0643(19) 0.094(2) 0.0489(17) 0.0118(17) 0.0121(15) C16 0.0199(10) 0.0257(10) 0.0260(10) -0.0073(8) -0.0023(8) -0.0056(8) C17 0.0349(13) 0.0366(12) 0.0264(11) -0.0043(9) -0.0055(9) -0.0107(10) C18 0.0485(15) 0.0456(14) 0.0260(11) -0.0113(10) -0.0059(10) -0.0114(12) C19 0.0410(14) 0.0336(12) 0.0438(14) -0.0183(10) -0.0081(11) -0.0038(11) C20 0.0358(13) 0.0260(11) 0.0428(13) -0.0049(9) -0.0044(10) -0.0056(10) C21 0.0285(12) 0.0270(11) 0.0297(11) -0.0040(9) -0.0010(9) -0.0084(9) C22 0.0690(18) 0.0430(14) 0.0250(12) -0.0010(10) -0.0106(12) -0.0245(13) C23 0.064(2) 0.117(3) 0.082(2) 0.055(2) -0.0013(18) -0.024(2) C24 0.061(2) 0.0492(17) 0.120(3) 0.0365(17) 0.0013(19) -0.0001(15) C25 0.0696(18) 0.0307(12) 0.0287(12) 0.0009(9) 0.0028(12) -0.0171(12) C26 0.071(2) 0.0533(16) 0.0501(16) 0.0051(13) 0.0172(14) -0.0200(15) C27 0.097(3) 0.162(3) 0.0413(16) 0.0370(19) -0.0344(17) -0.071(3) C28 0.0414(15) 0.0584(16) 0.0458(14) -0.0100(12) 0.0109(12) -0.0178(13) C29 0.0357(14) 0.0424(14) 0.0609(16) 0.0041(12) -0.0163(12) -0.0038(11) C30 0.0238(12) 0.0418(13) 0.0562(15) -0.0159(11) -0.0049(11) -0.0064(10) Si2 0.0248(3) 0.0236(3) 0.0228(3) 0.0020(2) 0.0003(2) -0.0012(2) N4 0.0262(10) 0.0245(9) 0.0266(9) 0.0037(7) -0.0008(7) -0.0022(7) N5 0.0251(9) 0.0185(8) 0.0245(8) 0.0022(7) -0.0004(7) -0.0014(7) N6 0.0267(9) 0.0209(8) 0.0228(8) 0.0016(7) -0.0002(7) -0.0046(7) C31 0.0283(12) 0.0181(9) 0.0173(9) -0.0024(7) -0.0021(8) -0.0059(9) C32 0.0250(11) 0.0250(11) 0.0357(12) 0.0021(9) -0.0033(9) -0.0004(9) C33 0.0231(11) 0.0267(11) 0.0384(12) -0.0009(9) 0.0016(9) -0.0042(9) C34 0.0231(11) 0.0202(10) 0.0245(10) 0.0041(8) 0.0003(8) 0.0009(8) C35 0.0310(12) 0.0204(10) 0.0306(11) 0.0028(8) -0.0014(9) -0.0026(9) C36 0.0427(14) 0.0229(11) 0.0408(13) 0.0050(9) -0.0015(11) -0.0073(10) C37 0.0479(15) 0.0359(13) 0.0360(13) 0.0159(10) 0.0005(11) -0.0105(11) C38 0.0415(14) 0.0412(13) 0.0233(11) 0.0061(9) -0.0032(10) -0.0024(11) C39 0.0301(12) 0.0257(10) 0.0264(11) 0.0032(8) -0.0055(9) 0.0008(9) C40 0.0426(14) 0.0238(11) 0.0319(11) -0.0030(9) 0.0020(10) -0.0068(10) C41 0.077(2) 0.0275(12) 0.0538(16) -0.0119(11) -0.0112(14) 0.0027(12) C42 0.0584(16) 0.0322(12) 0.0346(13) -0.0014(10) -0.0080(11) -0.0066(11) C43 0.0487(15) 0.0328(12) 0.0263(11) -0.0016(9) -0.0091(10) -0.0056(11) C44 0.0582(19) 0.0558(17) 0.087(2) -0.0216(15) -0.0221(16) -0.0121(15) C45 0.073(2) 0.0442(15) 0.0487(15) -0.0147(12) -0.0071(14) 0.0016(14) C46 0.0254(11) 0.0209(10) 0.0240(10) 0.0038(8) 0.0030(8) -0.0046(8) C47 0.0259(11) 0.0309(11) 0.0255(11) 0.0031(9) 0.0006(9) -0.0059(9) C48 0.0287(12) 0.0440(13) 0.0271(11) 0.0074(10) -0.0018(9) -0.0057(10) C49 0.0396(14) 0.0313(12) 0.0348(12) 0.0149(10) 0.0026(10) -0.0054(10) C50 0.0457(14) 0.0239(11) 0.0373(13) 0.0020(9) 0.0060(11) -0.0071(10) C51 0.0353(12) 0.0256(11) 0.0250(11) 0.0004(8) 0.0061(9) -0.0055(9) C52 0.0506(15) 0.0357(12) 0.0338(12) -0.0025(10) -0.0147(11) -0.0089(11) C53 0.0503(17) 0.0544(16) 0.0721(18) -0.0152(14) -0.0113(14) -0.0157(14) C54 0.0456(18) 0.077(2) 0.134(3) -0.066(2) -0.0041(19) 0.0017(16) C55 0.0590(16) 0.0246(11) 0.0299(12) -0.0026(9) -0.0022(11) -0.0068(11) C56 0.0676(19) 0.0652(18) 0.0397(14) -0.0132(12) 0.0048(13) -0.0299(15) C57 0.0448(15) 0.0431(14) 0.0510(15) -0.0110(11) -0.0047(12) -0.0051(12) C58 0.0497(16) 0.0353(13) 0.0351(13) 0.0029(10) 0.0079(11) 0.0037(11) C59 0.0323(13) 0.0333(12) 0.0408(13) 0.0096(10) 0.0008(10) 0.0044(10) C60 0.0373(14) 0.0433(14) 0.0521(15) -0.0017(11) -0.0149(12) -0.0035(11) _geom_special_details ; 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. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag Si1 N1 1.6771(18) . . yes Si1 C28 1.863(2) . . yes Si1 C29 1.866(2) . . yes Si1 C30 1.875(2) . . yes Si2 C58 1.864(2) . . yes Si2 C59 1.868(2) . . yes Si2 C60 1.868(2) . . yes Si2 N4 1.6771(17) . . yes N1 C1 1.263(3) . . yes N2 C4 1.440(2) . . yes N2 C1 1.400(2) . . yes N2 C2 1.394(3) . . yes N3 C3 1.386(3) . . yes N3 C16 1.443(2) . . yes N3 C1 1.399(2) . . yes N4 C31 1.265(3) . . yes N5 C31 1.397(2) . . yes N5 C32 1.387(3) . . yes N5 C34 1.441(2) . . yes N6 C33 1.392(3) . . yes N6 C46 1.434(2) . . yes N6 C31 1.397(2) . . yes C2 C3 1.335(3) . . no C4 C9 1.400(2) . . no C4 C5 1.407(3) . . no C5 C10 1.526(3) . . no C5 C6 1.394(3) . . no C6 C7 1.379(3) . . no C7 C8 1.377(3) . . no C8 C9 1.395(3) . . no C9 C13 1.524(3) . . no C10 C11 1.512(3) . . no C10 C12 1.531(3) . . no C13 C15 1.524(3) . . no C13 C14 1.517(3) . . no C16 C17 1.396(3) . . no C16 C21 1.399(3) . . no C17 C18 1.398(3) . . no C17 C22 1.521(3) . . no C18 C19 1.377(3) . . no C19 C20 1.374(3) . . no C20 C21 1.398(3) . . no C21 C25 1.516(3) . . no C22 C24 1.512(4) . . no C22 C23 1.524(4) . . no C25 C26 1.516(4) . . no C25 C27 1.522(5) . . no C2 H2 0.9500 . . no C3 H3 0.9500 . . no C6 H6 0.9500 . . no C7 H7 0.9500 . . no C8 H8 0.9500 . . no C10 H10 1.0000 . . no C11 H11C 0.9800 . . no C11 H11A 0.9800 . . no C11 H11B 0.9800 . . no C12 H12B 0.9800 . . no C12 H12C 0.9800 . . no C12 H12A 0.9800 . . no C13 H13 1.0000 . . no C14 H14A 0.9800 . . no C14 H14C 0.9800 . . no C14 H14B 0.9800 . . no C15 H15B 0.9800 . . no C15 H15A 0.9800 . . no C15 H15C 0.9800 . . no C18 H18 0.9500 . . no C19 H19 0.9500 . . no C20 H20 0.9500 . . no C22 H22 1.0000 . . no C23 H23B 0.9800 . . no C23 H23C 0.9800 . . no C23 H23A 0.9800 . . no C24 H24B 0.9800 . . no C24 H24C 0.9800 . . no C24 H24A 0.9800 . . no C25 H25 1.0000 . . no C26 H26C 0.9800 . . no C26 H26A 0.9800 . . no C26 H26B 0.9800 . . no C27 H27A 0.9800 . . no C27 H27B 0.9800 . . no C27 H27C 0.9800 . . no C28 H28A 0.9800 . . no C28 H28B 0.9800 . . no C28 H28C 0.9800 . . no C29 H29C 0.9800 . . no C29 H29A 0.9800 . . no C29 H29B 0.9800 . . no C30 H30B 0.9800 . . no C30 H30C 0.9800 . . no C30 H30A 0.9800 . . no C32 C33 1.336(3) . . no C34 C35 1.400(3) . . no C34 C39 1.397(3) . . no C35 C36 1.394(3) . . no C35 C40 1.524(3) . . no C36 C37 1.376(3) . . no C37 C38 1.381(3) . . no C38 C39 1.398(3) . . no C39 C43 1.521(3) . . no C40 C41 1.529(3) . . no C40 C42 1.531(3) . . no C43 C44 1.526(4) . . no C43 C45 1.521(3) . . no C46 C47 1.403(3) . . no C46 C51 1.397(3) . . no C47 C48 1.393(3) . . no C47 C52 1.524(3) . . no C48 C49 1.390(3) . . no C49 C50 1.375(3) . . no C50 C51 1.402(3) . . no C51 C55 1.528(3) . . no C52 C53 1.519(4) . . no C52 C54 1.523(4) . . no C55 C56 1.531(3) . . no C55 C57 1.521(3) . . no C32 H32 0.9500 . . no C33 H33 0.9500 . . no C36 H36 0.9500 . . no C37 H37 0.9500 . . no C38 H38 0.9500 . . no C40 H40 1.0000 . . no C41 H41A 0.9800 . . no C41 H41B 0.9800 . . no C41 H41C 0.9800 . . no C42 H42A 0.9800 . . no C42 H42B 0.9800 . . no C42 H42C 0.9800 . . no C43 H43 1.0000 . . no C44 H44A 0.9800 . . no C44 H44B 0.9800 . . no C44 H44C 0.9800 . . no C45 H45A 0.9800 . . no C45 H45B 0.9800 . . no C45 H45C 0.9800 . . no C48 H48 0.9500 . . no C49 H49 0.9500 . . no C50 H50 0.9500 . . no C52 H52 1.0000 . . no C53 H53A 0.9800 . . no C53 H53B 0.9800 . . no C53 H53C 0.9800 . . no C54 H54A 0.9800 . . no C54 H54B 0.9800 . . no C54 H54C 0.9800 . . no C55 H55 1.0000 . . no C56 H56A 0.9800 . . no C56 H56B 0.9800 . . no C56 H56C 0.9800 . . no C57 H57A 0.9800 . . no C57 H57B 0.9800 . . no C57 H57C 0.9800 . . no C58 H58A 0.9800 . . no C58 H58B 0.9800 . . no C58 H58C 0.9800 . . no C59 H59A 0.9800 . . no C59 H59B 0.9800 . . no C59 H59C 0.9800 . . no C60 H60A 0.9800 . . no C60 H60B 0.9800 . . no C60 H60C 0.9800 . . no loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Si1 C28 107.89(11) . . . yes N1 Si1 C29 108.81(8) . . . yes N1 Si1 C30 116.81(8) . . . yes C28 Si1 C29 107.81(11) . . . yes C28 Si1 C30 107.81(11) . . . yes C29 Si1 C30 107.40(10) . . . yes N4 Si2 C58 108.39(10) . . . yes N4 Si2 C59 117.85(9) . . . yes N4 Si2 C60 108.94(9) . . . yes C58 Si2 C59 106.71(9) . . . yes C58 Si2 C60 108.75(11) . . . yes C59 Si2 C60 105.91(10) . . . yes Si1 N1 C1 155.36(14) . . . yes C1 N2 C2 110.53(15) . . . yes C1 N2 C4 125.76(16) . . . yes C2 N2 C4 123.69(15) . . . yes C3 N3 C16 124.22(16) . . . yes C1 N3 C16 124.91(16) . . . yes C1 N3 C3 110.86(15) . . . yes Si2 N4 C31 157.79(14) . . . yes C31 N5 C32 110.70(15) . . . yes C31 N5 C34 123.98(16) . . . yes C32 N5 C34 125.25(16) . . . yes C31 N6 C33 110.60(15) . . . yes C31 N6 C46 123.32(16) . . . yes C33 N6 C46 126.07(16) . . . yes N1 C1 N3 125.59(17) . . . yes N2 C1 N3 102.86(15) . . . yes N1 C1 N2 131.55(18) . . . yes N2 C2 C3 107.78(17) . . . yes N3 C3 C2 107.93(17) . . . yes C5 C4 C9 122.59(17) . . . no N2 C4 C9 118.61(16) . . . yes N2 C4 C5 118.78(16) . . . yes C6 C5 C10 121.68(17) . . . no C4 C5 C6 117.05(16) . . . no C4 C5 C10 121.27(17) . . . no C5 C6 C7 121.23(18) . . . no C6 C7 C8 120.67(18) . . . no C7 C8 C9 120.84(18) . . . no C4 C9 C8 117.62(17) . . . no C8 C9 C13 120.27(16) . . . no C4 C9 C13 122.11(16) . . . no C5 C10 C12 112.85(17) . . . no C11 C10 C12 108.36(19) . . . no C5 C10 C11 111.45(17) . . . no C9 C13 C14 111.82(17) . . . no C9 C13 C15 110.85(18) . . . no C14 C13 C15 110.89(18) . . . no C17 C16 C21 122.90(18) . . . no N3 C16 C21 118.22(16) . . . yes N3 C16 C17 118.85(16) . . . yes C16 C17 C22 121.94(18) . . . no C18 C17 C22 120.95(18) . . . no C16 C17 C18 117.09(18) . . . no C17 C18 C19 121.11(19) . . . no C18 C19 C20 120.7(2) . . . no C19 C20 C21 120.91(19) . . . no C16 C21 C20 117.30(18) . . . no C20 C21 C25 120.77(18) . . . no C16 C21 C25 121.88(18) . . . no C17 C22 C23 112.5(2) . . . no C23 C22 C24 110.4(2) . . . no C17 C22 C24 111.4(2) . . . no C26 C25 C27 110.5(2) . . . no C21 C25 C27 109.1(2) . . . no C21 C25 C26 114.0(2) . . . no N2 C2 H2 126.00 . . . no C3 C2 H2 126.00 . . . no N3 C3 H3 126.00 . . . no C2 C3 H3 126.00 . . . no C7 C6 H6 119.00 . . . no C5 C6 H6 119.00 . . . no C6 C7 H7 120.00 . . . no C8 C7 H7 120.00 . . . no C7 C8 H8 120.00 . . . no C9 C8 H8 120.00 . . . no C12 C10 H10 108.00 . . . no C11 C10 H10 108.00 . . . no C5 C10 H10 108.00 . . . no C10 C11 H11C 109.00 . . . no C10 C11 H11B 109.00 . . . no C10 C11 H11A 109.00 . . . no H11A C11 H11C 109.00 . . . no H11B C11 H11C 109.00 . . . no H11A C11 H11B 110.00 . . . no C10 C12 H12C 109.00 . . . no H12A C12 H12B 109.00 . . . no C10 C12 H12A 110.00 . . . no C10 C12 H12B 109.00 . . . no H12B C12 H12C 109.00 . . . no H12A C12 H12C 109.00 . . . no C9 C13 H13 108.00 . . . no C15 C13 H13 108.00 . . . no C14 C13 H13 108.00 . . . no C13 C14 H14C 109.00 . . . no C13 C14 H14B 109.00 . . . no C13 C14 H14A 109.00 . . . no H14B C14 H14C 109.00 . . . no H14A C14 H14B 110.00 . . . no H14A C14 H14C 109.00 . . . no C13 C15 H15A 109.00 . . . no C13 C15 H15B 109.00 . . . no C13 C15 H15C 109.00 . . . no H15A C15 H15B 110.00 . . . no H15A C15 H15C 109.00 . . . no H15B C15 H15C 110.00 . . . no C19 C18 H18 119.00 . . . no C17 C18 H18 119.00 . . . no C18 C19 H19 120.00 . . . no C20 C19 H19 120.00 . . . no C19 C20 H20 119.00 . . . no C21 C20 H20 120.00 . . . no C23 C22 H22 107.00 . . . no C17 C22 H22 107.00 . . . no C24 C22 H22 107.00 . . . no H23A C23 H23C 109.00 . . . no H23B C23 H23C 110.00 . . . no C22 C23 H23A 109.00 . . . no C22 C23 H23B 109.00 . . . no C22 C23 H23C 110.00 . . . no H23A C23 H23B 109.00 . . . no H24B C24 H24C 109.00 . . . no C22 C24 H24C 109.00 . . . no C22 C24 H24A 109.00 . . . no C22 C24 H24B 109.00 . . . no H24A C24 H24B 110.00 . . . no H24A C24 H24C 110.00 . . . no C26 C25 H25 108.00 . . . no C21 C25 H25 108.00 . . . no C27 C25 H25 108.00 . . . no H26A C26 H26C 109.00 . . . no H26B C26 H26C 110.00 . . . no H26A C26 H26B 109.00 . . . no C25 C26 H26A 109.00 . . . no C25 C26 H26B 109.00 . . . no C25 C26 H26C 109.00 . . . no H27B C27 H27C 110.00 . . . no C25 C27 H27B 109.00 . . . no C25 C27 H27C 109.00 . . . no C25 C27 H27A 109.00 . . . no H27A C27 H27C 109.00 . . . no H27A C27 H27B 109.00 . . . no Si1 C28 H28C 110.00 . . . no Si1 C28 H28B 109.00 . . . no Si1 C28 H28A 109.00 . . . no H28A C28 H28C 110.00 . . . no H28B C28 H28C 109.00 . . . no H28A C28 H28B 109.00 . . . no Si1 C29 H29C 109.00 . . . no H29A C29 H29B 110.00 . . . no Si1 C29 H29A 109.00 . . . no Si1 C29 H29B 110.00 . . . no H29B C29 H29C 109.00 . . . no H29A C29 H29C 109.00 . . . no H30B C30 H30C 110.00 . . . no H30A C30 H30C 109.00 . . . no Si1 C30 H30A 109.00 . . . no Si1 C30 H30B 109.00 . . . no Si1 C30 H30C 109.00 . . . no H30A C30 H30B 109.00 . . . no N4 C31 N5 125.62(17) . . . yes N4 C31 N6 131.35(17) . . . yes N5 C31 N6 103.03(15) . . . yes N5 C32 C33 107.97(17) . . . yes N6 C33 C32 107.69(17) . . . yes N5 C34 C35 118.14(16) . . . yes N5 C34 C39 118.57(16) . . . yes C35 C34 C39 123.28(17) . . . no C34 C35 C36 117.17(18) . . . no C34 C35 C40 121.11(17) . . . no C36 C35 C40 121.69(17) . . . no C35 C36 C37 120.94(19) . . . no C36 C37 C38 120.7(2) . . . no C37 C38 C39 121.05(19) . . . no C34 C39 C38 116.86(17) . . . no C34 C39 C43 121.39(17) . . . no C38 C39 C43 121.75(18) . . . no C35 C40 C41 113.59(17) . . . no C35 C40 C42 110.64(16) . . . no C41 C40 C42 109.65(18) . . . no C39 C43 C44 110.29(17) . . . no C39 C43 C45 113.26(18) . . . no C44 C43 C45 110.6(2) . . . no N6 C46 C47 118.56(16) . . . yes N6 C46 C51 118.19(16) . . . yes C47 C46 C51 123.25(17) . . . no C46 C47 C48 117.23(18) . . . no C46 C47 C52 121.33(18) . . . no C48 C47 C52 121.36(18) . . . no C47 C48 C49 120.61(18) . . . no C48 C49 C50 120.81(19) . . . no C49 C50 C51 120.97(18) . . . no C46 C51 C50 116.96(17) . . . no C46 C51 C55 121.61(16) . . . no C50 C51 C55 121.42(17) . . . no C47 C52 C53 113.62(19) . . . no C47 C52 C54 110.4(2) . . . no C53 C52 C54 109.8(2) . . . no C51 C55 C56 111.5(2) . . . no C51 C55 C57 112.37(17) . . . no C56 C55 C57 110.99(18) . . . no N5 C32 H32 126.00 . . . no C33 C32 H32 126.00 . . . no N6 C33 H33 126.00 . . . no C32 C33 H33 126.00 . . . no C35 C36 H36 119.00 . . . no C37 C36 H36 120.00 . . . no C36 C37 H37 120.00 . . . no C38 C37 H37 120.00 . . . no C37 C38 H38 119.00 . . . no C39 C38 H38 119.00 . . . no C35 C40 H40 108.00 . . . no C41 C40 H40 108.00 . . . no C42 C40 H40 108.00 . . . no C40 C41 H41A 110.00 . . . no C40 C41 H41B 109.00 . . . no C40 C41 H41C 109.00 . . . no H41A C41 H41B 109.00 . . . no H41A C41 H41C 109.00 . . . no H41B C41 H41C 109.00 . . . no C40 C42 H42A 109.00 . . . no C40 C42 H42B 109.00 . . . no C40 C42 H42C 109.00 . . . no H42A C42 H42B 110.00 . . . no H42A C42 H42C 109.00 . . . no H42B C42 H42C 109.00 . . . no C39 C43 H43 107.00 . . . no C44 C43 H43 107.00 . . . no C45 C43 H43 108.00 . . . no C43 C44 H44A 109.00 . . . no C43 C44 H44B 110.00 . . . no C43 C44 H44C 109.00 . . . no H44A C44 H44B 110.00 . . . no H44A C44 H44C 109.00 . . . no H44B C44 H44C 109.00 . . . no C43 C45 H45A 109.00 . . . no C43 C45 H45B 109.00 . . . no C43 C45 H45C 109.00 . . . no H45A C45 H45B 110.00 . . . no H45A C45 H45C 110.00 . . . no H45B C45 H45C 109.00 . . . no C47 C48 H48 120.00 . . . no C49 C48 H48 120.00 . . . no C48 C49 H49 120.00 . . . no C50 C49 H49 120.00 . . . no C49 C50 H50 119.00 . . . no C51 C50 H50 120.00 . . . no C47 C52 H52 108.00 . . . no C53 C52 H52 108.00 . . . no C54 C52 H52 108.00 . . . no C52 C53 H53A 109.00 . . . no C52 C53 H53B 110.00 . . . no C52 C53 H53C 109.00 . . . no H53A C53 H53B 109.00 . . . no H53A C53 H53C 109.00 . . . no H53B C53 H53C 109.00 . . . no C52 C54 H54A 109.00 . . . no C52 C54 H54B 109.00 . . . no C52 C54 H54C 109.00 . . . no H54A C54 H54B 110.00 . . . no H54A C54 H54C 110.00 . . . no H54B C54 H54C 109.00 . . . no C51 C55 H55 107.00 . . . no C56 C55 H55 107.00 . . . no C57 C55 H55 107.00 . . . no C55 C56 H56A 109.00 . . . no C55 C56 H56B 110.00 . . . no C55 C56 H56C 109.00 . . . no H56A C56 H56B 109.00 . . . no H56A C56 H56C 109.00 . . . no H56B C56 H56C 110.00 . . . no C55 C57 H57A 109.00 . . . no C55 C57 H57B 109.00 . . . no C55 C57 H57C 109.00 . . . no H57A C57 H57B 110.00 . . . no H57A C57 H57C 109.00 . . . no H57B C57 H57C 109.00 . . . no Si2 C58 H58A 109.00 . . . no Si2 C58 H58B 109.00 . . . no Si2 C58 H58C 109.00 . . . no H58A C58 H58B 109.00 . . . no H58A C58 H58C 110.00 . . . no H58B C58 H58C 109.00 . . . no Si2 C59 H59A 109.00 . . . no Si2 C59 H59B 109.00 . . . no Si2 C59 H59C 110.00 . . . no H59A C59 H59B 109.00 . . . no H59A C59 H59C 110.00 . . . no H59B C59 H59C 109.00 . . . no Si2 C60 H60A 109.00 . . . no Si2 C60 H60B 110.00 . . . no Si2 C60 H60C 109.00 . . . no H60A C60 H60B 109.00 . . . no H60A C60 H60C 110.00 . . . no H60B C60 H60C 109.00 . . . no _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.419 _refine_diff_density_min -0.282 _refine_diff_density_rms 0.046 #============================================================================= # end of cif data for "sran9x" (compound 2e in manuscript) #============================================================================= #============================================================================= # cif data for "dpet2" (compound 3a in manuscript) #============================================================================= data_dpet2 _database_code_depnum_ccdc_archive 'CCDC 618032' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety 'C11 H21 N3' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C11 H21 N3' _chemical_formula_weight 195.31 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,1/2+y,1/2-z 3 -x,-y,-z 4 x,1/2-y,1/2+z _cell_length_a 9.80420(10) _cell_length_b 11.0624(2) _cell_length_c 11.6724(2) _cell_angle_alpha 90 _cell_angle_beta 112.3293(7) _cell_angle_gamma 90 _cell_volume 1171.04(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173 _cell_measurement_reflns_used 3473 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 25.34 _exptl_crystal_description fragment _exptl_crystal_colour colourless _exptl_crystal_size_max 0.300 _exptl_crystal_size_mid 0.150 _exptl_crystal_size_min 0.130 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.108 _exptl_crystal_density_method none _exptl_crystal_F_000 432 _exptl_absorpt_coefficient_mu 0.068 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.980 _exptl_absorpt_correction_T_max 0.991 _exptl_special_details ; ? ; _diffrn_ambient_temperature 133(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'NONIUS FR 591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device ' \k-geometry diffractometer ' _diffrn_measurement_device_type ' Nonius \k-CCD diffractometer' _diffrn_measurement_method ' phi- and omega-rotation ' _diffrn_detector ' CCD plate ' _diffrn_detector_area_resol_mean 18 # 9 for binned mode _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 4140 _diffrn_reflns_av_R_equivalents 0.0216 _diffrn_reflns_av_sigmaI/netI 0.0299 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.25 _diffrn_reflns_theta_max 25.34 _reflns_number_total 2137 _reflns_number_gt 1808 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Kappa-CCD Control Software (Nonius, 2001a)' _computing_cell_refinement 'DENZO (Nonius, 2001b)' _computing_data_reduction 'DENZO (Nonius, 2001b)' _computing_structure_solution 'SIR92 (Altomare, 1994)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1998)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'PLATON (Spek, 2003)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme sigma _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(Fo^2^)+(0.0482P)^2^+0.2400P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment 'N-H free, rigid methyls, other riding' _refine_ls_extinction_method none _refine_ls_number_reflns 2137 _refine_ls_number_parameters 137 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0462 _refine_ls_R_factor_gt 0.0378 _refine_ls_wR_factor_ref 0.0981 _refine_ls_wR_factor_gt 0.0936 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags N1 N Uani 0.34960(13) 0.06599(10) 0.92706(10) 1.000 0.0323(3) . . N2 N Uani 0.15763(11) 0.11610(9) 0.73697(9) 1.000 0.0260(3) . . N3 N Uani 0.35959(10) 0.22740(9) 0.78673(9) 1.000 0.0257(3) . . C1 C Uani 0.29751(13) 0.13174(10) 0.82802(11) 1.000 0.0244(3) . . C2 C Uani 0.13898(14) 0.19739(11) 0.64094(11) 1.000 0.0288(4) . . C3 C Uani 0.26043(13) 0.26458(12) 0.67042(11) 1.000 0.0284(4) . . C4 C Uani 0.04770(13) 0.02748(11) 0.74529(11) 1.000 0.0274(4) . . C5 C Uani 0.10532(15) -0.10053(12) 0.74551(14) 1.000 0.0381(5) . . C6 C Uani -0.09656(14) 0.04327(14) 0.63384(13) 1.000 0.0412(5) . . C7 C Uani 0.01844(16) 0.05128(14) 0.86322(14) 1.000 0.0402(5) . . C8 C Uani 0.50211(13) 0.28698(10) 0.86109(11) 1.000 0.0261(4) . . C9 C Uani 0.51680(16) 0.40269(12) 0.79484(13) 1.000 0.0364(4) . . C10 C Uani 0.63034(14) 0.20217(12) 0.87392(13) 1.000 0.0352(4) . . C11 C Uani 0.50255(16) 0.32337(12) 0.98813(12) 1.000 0.0352(4) . . H1 H Uiso 0.4405(17) 0.0859(14) 0.9712(14) 1.000 0.040(4) . . H2 H Uiso 0.05380 0.20380 0.56680 1.000 0.0350 calc R H3 H Uiso 0.27670 0.32690 0.62100 1.000 0.0340 calc R H51 H Uiso 0.19750 -0.11110 0.81750 1.000 0.0570 calc R H52 H Uiso 0.12340 -0.11390 0.66950 1.000 0.0570 calc R H53 H Uiso 0.03210 -0.15880 0.74960 1.000 0.0570 calc R H61 H Uiso -0.13310 0.12590 0.63280 1.000 0.0620 calc R H62 H Uiso -0.16970 -0.01430 0.63950 1.000 0.0620 calc R H63 H Uiso -0.07960 0.02840 0.55750 1.000 0.0620 calc R H71 H Uiso -0.01720 0.13430 0.86180 1.000 0.0600 calc R H72 H Uiso 0.11000 0.04030 0.93580 1.000 0.0600 calc R H73 H Uiso -0.05620 -0.00550 0.86740 1.000 0.0600 calc R H91 H Uiso 0.43290 0.45590 0.78390 1.000 0.0550 calc R H92 H Uiso 0.51830 0.38210 0.71370 1.000 0.0550 calc R H93 H Uiso 0.60860 0.44410 0.84460 1.000 0.0550 calc R H101 H Uiso 0.62010 0.12730 0.91480 1.000 0.0530 calc R H102 H Uiso 0.72370 0.24160 0.92360 1.000 0.0530 calc R H103 H Uiso 0.62940 0.18330 0.79160 1.000 0.0530 calc R H111 H Uiso 0.41270 0.36900 0.97690 1.000 0.0530 calc R H112 H Uiso 0.58900 0.37380 1.03160 1.000 0.0530 calc R H113 H Uiso 0.50620 0.25060 1.03700 1.000 0.0530 calc R loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0286(6) 0.0312(6) 0.0291(6) 0.0095(5) 0.0021(5) -0.0036(5) N2 0.0233(5) 0.0276(5) 0.0240(5) 0.0039(4) 0.0054(4) -0.0019(4) N3 0.0254(5) 0.0247(5) 0.0242(5) 0.0040(4) 0.0063(4) -0.0024(4) C1 0.0244(6) 0.0225(6) 0.0253(6) 0.0011(5) 0.0082(5) -0.0009(5) C2 0.0280(7) 0.0341(7) 0.0209(6) 0.0060(5) 0.0056(5) 0.0029(5) C3 0.0316(7) 0.0293(7) 0.0241(7) 0.0071(5) 0.0104(5) 0.0020(5) C4 0.0233(6) 0.0292(7) 0.0296(7) -0.0011(5) 0.0098(5) -0.0040(5) C5 0.0375(8) 0.0292(7) 0.0481(9) -0.0034(6) 0.0167(7) -0.0053(6) C6 0.0273(7) 0.0491(9) 0.0416(9) 0.0014(7) 0.0067(6) -0.0075(6) C7 0.0406(8) 0.0455(8) 0.0412(8) -0.0050(7) 0.0231(7) -0.0082(6) C8 0.0252(6) 0.0244(6) 0.0277(7) -0.0008(5) 0.0090(5) -0.0045(5) C9 0.0413(8) 0.0285(7) 0.0407(8) 0.0027(6) 0.0170(7) -0.0076(6) C10 0.0288(7) 0.0329(7) 0.0442(8) -0.0021(6) 0.0142(6) -0.0019(5) C11 0.0387(8) 0.0341(7) 0.0332(7) -0.0069(6) 0.0140(6) -0.0082(6) _geom_special_details ; 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. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.2953(16) . . yes N2 C1 1.3902(17) . . yes N2 C2 1.3938(16) . . yes N2 C4 1.4872(17) . . yes N3 C1 1.3948(16) . . yes N3 C3 1.3981(16) . . yes N3 C8 1.4895(16) . . yes N1 H1 0.871(17) . . no C2 C3 1.3332(19) . . no C4 C6 1.5248(19) . . no C4 C7 1.532(2) . . no C4 C5 1.5243(18) . . no C8 C10 1.5298(19) . . no C8 C11 1.5350(18) . . no C8 C9 1.5303(18) . . no C2 H2 0.9500 . . no C3 H3 0.9500 . . no C5 H51 0.9800 . . no C5 H52 0.9800 . . no C5 H53 0.9800 . . no C6 H61 0.9800 . . no C6 H62 0.9800 . . no C6 H63 0.9800 . . no C7 H71 0.9800 . . no C7 H72 0.9800 . . no C7 H73 0.9800 . . no C9 H91 0.9800 . . no C9 H92 0.9800 . . no C9 H93 0.9800 . . no C10 H101 0.9800 . . no C10 H102 0.9800 . . no C10 H103 0.9800 . . no C11 H111 0.9800 . . no C11 H112 0.9800 . . no C11 H113 0.9800 . . no loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N2 C2 108.93(10) . . . yes C1 N2 C4 124.13(10) . . . yes C2 N2 C4 126.94(10) . . . yes C1 N3 C3 108.97(10) . . . yes C1 N3 C8 124.77(10) . . . yes C3 N3 C8 126.01(10) . . . yes C1 N1 H1 110.7(10) . . . no N1 C1 N2 123.53(12) . . . yes N1 C1 N3 131.19(12) . . . yes N2 C1 N3 105.28(10) . . . yes N2 C2 C3 108.71(11) . . . yes N3 C3 C2 108.06(11) . . . yes N2 C4 C5 109.59(11) . . . yes N2 C4 C6 109.21(10) . . . yes C5 C4 C6 109.32(11) . . . no C5 C4 C7 110.73(11) . . . no N2 C4 C7 109.46(10) . . . yes C6 C4 C7 108.50(12) . . . no N3 C8 C10 109.86(10) . . . yes N3 C8 C11 109.68(11) . . . yes N3 C8 C9 108.86(10) . . . yes C9 C8 C11 107.61(10) . . . no C10 C8 C11 111.45(11) . . . no C9 C8 C10 109.32(11) . . . no N2 C2 H2 126.00 . . . no C3 C2 H2 126.00 . . . no N3 C3 H3 126.00 . . . no C2 C3 H3 126.00 . . . no C4 C5 H51 109.00 . . . no C4 C5 H52 109.00 . . . no C4 C5 H53 109.00 . . . no H51 C5 H52 109.00 . . . no H51 C5 H53 110.00 . . . no H52 C5 H53 109.00 . . . no C4 C6 H61 109.00 . . . no C4 C6 H62 109.00 . . . no C4 C6 H63 109.00 . . . no H61 C6 H62 109.00 . . . no H61 C6 H63 109.00 . . . no H62 C6 H63 109.00 . . . no C4 C7 H71 109.00 . . . no C4 C7 H72 109.00 . . . no C4 C7 H73 109.00 . . . no H71 C7 H72 110.00 . . . no H71 C7 H73 109.00 . . . no H72 C7 H73 109.00 . . . no C8 C9 H91 109.00 . . . no C8 C9 H92 109.00 . . . no C8 C9 H93 109.00 . . . no H91 C9 H92 110.00 . . . no H91 C9 H93 109.00 . . . no H92 C9 H93 110.00 . . . no C8 C10 H101 109.00 . . . no C8 C10 H102 109.00 . . . no C8 C10 H103 109.00 . . . no H101 C10 H102 109.00 . . . no H101 C10 H103 109.00 . . . no H102 C10 H103 109.00 . . . no C8 C11 H111 109.00 . . . no C8 C11 H112 110.00 . . . no C8 C11 H113 109.00 . . . no H111 C11 H112 109.00 . . . no H111 C11 H113 109.00 . . . no H112 C11 H113 109.00 . . . no _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.160 _refine_diff_density_min -0.195 _refine_diff_density_rms 0.032 #============================================================================= # end of cif data for "dpet2" (compound 3a in manuscript) #============================================================================= #============================================================================= # cif data for "dpet4" (compound 3b in manuscript) #============================================================================= data_dpet4 _database_code_depnum_ccdc_archive 'CCDC 618033' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety 'C11 H21 N3' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C11 H21 N3' _chemical_formula_weight 195.31 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall 'C -2yc' _symmetry_space_group_name_H-M 'C c' loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 x,-y,1/2+z 3 1/2+x,1/2+y,z 4 1/2+x,1/2-y,1/2+z _cell_length_a 7.5606(2) _cell_length_b 16.9628(4) _cell_length_c 9.1745(2) _cell_angle_alpha 90 _cell_angle_beta 92.2557(8) _cell_angle_gamma 90 _cell_volume 1175.71(5) _cell_formula_units_Z 4 _cell_measurement_temperature 173 _cell_measurement_reflns_used 1119 _cell_measurement_theta_min 25.40 _cell_measurement_theta_max 2.40 _exptl_crystal_description fragment _exptl_crystal_colour colourless _exptl_crystal_size_max 0.360 _exptl_crystal_size_mid 0.180 _exptl_crystal_size_min 0.150 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.103 _exptl_crystal_density_method none _exptl_crystal_F_000 432 _exptl_absorpt_coefficient_mu 0.068 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.976 _exptl_absorpt_correction_T_max 0.990 _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'NONIUS FR 591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device ' \k-geometry diffractometer ' _diffrn_measurement_device_type ' Nonius \k-CCD diffractometer' _diffrn_measurement_method ' phi- and omega-rotation ' _diffrn_detector ' CCD plate ' _diffrn_detector_area_resol_mean 18 # 9 for binned mode _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 1080 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0179 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.40 _diffrn_reflns_theta_max 25.40 _reflns_number_total 1080 _reflns_number_gt 1024 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Kappa-CCD Control Software (Nonius, 2001a)' _computing_cell_refinement 'DENZO (Nonius, 2001b)' _computing_data_reduction 'DENZO (Nonius, 2001b)' _computing_structure_solution 'SIR92 (Altomare, 1994)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1998)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'PLATON (Spek, 2003)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme sigma _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(Fo^2^)+(0.0346P)^2^+0.2752P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_number_reflns 1080 _refine_ls_number_parameters 211 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0326 _refine_ls_R_factor_gt 0.0296 _refine_ls_wR_factor_ref 0.0673 _refine_ls_wR_factor_gt 0.0657 _refine_ls_goodness_of_fit_ref 1.104 _refine_ls_restrained_S_all 1.103 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags N1 N Uani -0.2111(2) 0.15921(12) 0.6974(2) 1.000 0.0404(6) . . N2 N Uani 0.0396(2) 0.07790(11) 0.66868(18) 1.000 0.0310(5) . . N3 N Uani 0.0702(2) 0.17087(10) 0.8354(2) 1.000 0.0330(5) . . C1 C Uani -0.0498(3) 0.13940(12) 0.7327(2) 1.000 0.0312(6) . . C2 C Uani 0.2163(3) 0.07642(12) 0.7244(2) 1.000 0.0310(6) . . C3 C Uani 0.2344(3) 0.13237(12) 0.8263(2) 1.000 0.0308(6) . . C4 C Uani -0.0159(3) 0.04122(13) 0.5285(2) 1.000 0.0352(7) . . C5 C Uani -0.1979(3) 0.00410(16) 0.5292(3) 1.000 0.0420(8) . . C6 C Uani -0.0008(4) 0.10018(16) 0.4051(3) 1.000 0.0462(8) . . C7 C Uani 0.3480(3) 0.01775(16) 0.6744(3) 1.000 0.0449(8) . . C8 C Uani 0.3924(3) 0.15478(16) 0.9195(3) 1.000 0.0417(8) . . C9 C Uani 0.0390(3) 0.24025(13) 0.9276(2) 1.000 0.0354(7) . . C10 C Uani 0.0038(4) 0.31413(15) 0.8375(3) 1.000 0.0448(8) . . C11 C Uani -0.1025(4) 0.22478(18) 1.0379(3) 1.000 0.0478(9) . . H1 H Uiso -0.246(4) 0.2011(18) 0.755(3) 1.000 0.046(7) . . H4 H Uiso 0.066(3) -0.0018(15) 0.516(3) 1.000 0.033(6) . . H9 H Uiso 0.154(4) 0.2496(16) 0.989(3) 1.000 0.043(7) . . H51 H Uiso -0.216(4) -0.0344(17) 0.611(3) 1.000 0.053(7) . . H52 H Uiso -0.214(4) -0.0272(17) 0.437(3) 1.000 0.055(8) . . H53 H Uiso -0.293(4) 0.0450(17) 0.531(3) 1.000 0.050(7) . . H61 H Uiso 0.120(5) 0.1239(19) 0.411(4) 1.000 0.069(9) . . H62 H Uiso -0.083(4) 0.146(2) 0.420(4) 1.000 0.070(9) . . H63 H Uiso -0.027(4) 0.0744(15) 0.316(3) 1.000 0.053(7) . . H71 H Uiso 0.364(4) 0.0175(17) 0.567(3) 1.000 0.055(8) . . H72 H Uiso 0.309(4) -0.0410(19) 0.695(3) 1.000 0.062(8) . . H73 H Uiso 0.461(4) 0.0270(16) 0.727(3) 1.000 0.059(8) . . H81 H Uiso 0.489(4) 0.1185(18) 0.901(4) 1.000 0.066(9) . . H82 H Uiso 0.374(4) 0.1474(17) 1.027(3) 1.000 0.052(8) . . H83 H Uiso 0.425(4) 0.209(2) 0.903(3) 1.000 0.059(8) . . H101 H Uiso -0.109(5) 0.3106(18) 0.783(3) 1.000 0.064(9) . . H102 H Uiso 0.107(5) 0.3257(16) 0.766(4) 1.000 0.066(9) . . H103 H Uiso 0.005(4) 0.3591(19) 0.898(3) 1.000 0.054(8) . . H111 H Uiso -0.071(4) 0.180(2) 1.098(4) 1.000 0.067(9) . . H112 H Uiso -0.226(5) 0.2150(18) 0.990(3) 1.000 0.063(9) . . H113 H Uiso -0.113(4) 0.2695(19) 1.100(3) 1.000 0.057(8) . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0323(11) 0.0466(12) 0.0418(10) -0.0112(9) -0.0031(8) 0.0089(9) N2 0.0283(9) 0.0331(9) 0.0316(9) -0.0051(7) -0.0003(7) 0.0028(7) N3 0.0327(9) 0.0353(9) 0.0308(9) -0.0060(8) -0.0028(7) 0.0039(7) C1 0.0325(11) 0.0331(11) 0.0279(10) -0.0020(9) 0.0004(8) 0.0000(9) C2 0.0297(11) 0.0325(11) 0.0310(10) 0.0042(9) 0.0022(8) 0.0002(8) C3 0.0296(11) 0.0300(11) 0.0327(11) 0.0070(9) -0.0005(8) -0.0003(8) C4 0.0373(12) 0.0337(11) 0.0344(11) -0.0092(9) 0.0002(9) 0.0023(10) C5 0.0409(14) 0.0394(13) 0.0452(14) -0.0033(12) -0.0036(11) -0.0069(11) C6 0.0563(16) 0.0503(15) 0.0320(13) -0.0052(11) 0.0034(10) -0.0093(13) C7 0.0369(14) 0.0456(14) 0.0523(15) -0.0033(12) 0.0036(11) 0.0110(10) C8 0.0365(13) 0.0409(14) 0.0466(14) 0.0030(11) -0.0113(11) -0.0021(11) C9 0.0396(13) 0.0348(12) 0.0317(11) -0.0067(9) -0.0010(10) 0.0006(9) C10 0.0502(15) 0.0356(13) 0.0482(14) -0.0011(11) -0.0014(12) 0.0027(11) C11 0.0610(17) 0.0500(15) 0.0331(12) -0.0063(12) 0.0105(12) -0.0015(12) _geom_special_details ; 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. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.294(3) . . yes N2 C1 1.386(3) . . yes N2 C2 1.412(3) . . yes N2 C4 1.475(3) . . yes N3 C1 1.389(3) . . yes N3 C3 1.408(3) . . yes N3 C9 1.474(3) . . yes N1 H1 0.93(3) . . no C2 C7 1.493(3) . . no C2 C3 1.335(3) . . no C3 C8 1.491(3) . . no C4 C5 1.514(3) . . no C4 C6 1.518(3) . . no C9 C10 1.519(3) . . no C9 C11 1.524(4) . . no C4 H4 0.97(2) . . no C5 H51 1.01(3) . . no C5 H52 1.00(3) . . no C5 H53 1.00(3) . . no C6 H61 1.00(4) . . no C6 H62 1.01(3) . . no C6 H63 0.94(3) . . no C7 H71 1.00(3) . . no C7 H72 1.06(3) . . no C7 H73 0.98(3) . . no C8 H81 0.98(3) . . no C8 H82 1.01(3) . . no C8 H83 0.97(3) . . no C9 H9 1.03(3) . . no C10 H101 0.97(4) . . no C10 H102 1.06(4) . . no C10 H103 0.94(3) . . no C11 H111 0.96(3) . . no C11 H112 1.03(4) . . no C11 H113 0.95(3) . . no loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N2 C2 109.28(17) . . . yes C1 N2 C4 124.08(17) . . . yes C2 N2 C4 122.75(16) . . . yes C1 N3 C3 109.60(17) . . . yes C1 N3 C9 125.54(17) . . . yes C3 N3 C9 124.46(17) . . . yes C1 N1 H1 110.0(18) . . . no N1 C1 N3 130.86(19) . . . yes N2 C1 N3 105.09(17) . . . yes N1 C1 N2 124.05(18) . . . yes N2 C2 C3 108.08(19) . . . yes N2 C2 C7 122.26(18) . . . yes C3 C2 C7 129.6(2) . . . no N3 C3 C2 107.75(19) . . . yes N3 C3 C8 122.42(18) . . . yes C2 C3 C8 129.8(2) . . . no N2 C4 C6 110.19(19) . . . yes C5 C4 C6 111.9(2) . . . no N2 C4 C5 113.54(18) . . . yes N3 C9 C11 112.09(19) . . . yes C10 C9 C11 113.0(2) . . . no N3 C9 C10 112.03(17) . . . yes N2 C4 H4 105.1(16) . . . no C5 C4 H4 105.9(14) . . . no C6 C4 H4 110.0(16) . . . no C4 C5 H51 115.0(17) . . . no C4 C5 H52 107.3(17) . . . no C4 C5 H53 111.5(17) . . . no H51 C5 H52 106(2) . . . no H51 C5 H53 109(2) . . . no H52 C5 H53 109(2) . . . no C4 C6 H61 109(2) . . . no C4 C6 H62 110(2) . . . no C4 C6 H63 108.8(16) . . . no H61 C6 H62 105(3) . . . no H61 C6 H63 113(3) . . . no H62 C6 H63 112(3) . . . no C2 C7 H71 114.5(17) . . . no C2 C7 H72 112.3(17) . . . no C2 C7 H73 108.8(16) . . . no H71 C7 H72 103(2) . . . no H71 C7 H73 111(2) . . . no H72 C7 H73 108(2) . . . no C3 C8 H81 109(2) . . . no C3 C8 H82 113.0(17) . . . no C3 C8 H83 110.9(17) . . . no H81 C8 H82 103(3) . . . no H81 C8 H83 112(3) . . . no H82 C8 H83 109(2) . . . no N3 C9 H9 106.6(15) . . . no C10 C9 H9 107.3(15) . . . no C11 C9 H9 105.3(16) . . . no C9 C10 H101 111.1(18) . . . no C9 C10 H102 111.9(17) . . . no C9 C10 H103 110.5(18) . . . no H101 C10 H102 110(3) . . . no H101 C10 H103 110(3) . . . no H102 C10 H103 103(2) . . . no C9 C11 H111 110.6(19) . . . no C9 C11 H112 113.1(17) . . . no C9 C11 H113 109.7(18) . . . no H111 C11 H112 109(3) . . . no H111 C11 H113 108(3) . . . no H112 C11 H113 107(3) . . . no _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.092 _refine_diff_density_min -0.156 _refine_diff_density_rms 0.028 #============================================================================= # end of cif data for "dpet4" (compound 3b in manuscript) #============================================================================= #============================================================================= # cif data for "dpet13x" (compound 3c in manuscript) #============================================================================= data_dpet13x _database_code_depnum_ccdc_archive 'CCDC 618034' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety 'C9 H17 N3' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C9 H17 N3' _chemical_formula_weight 167.26 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y+1/2, z+1/2' '-x, -y, -z' '-x, y-1/2, -z-1/2' _cell_length_a 10.3194(11) _cell_length_b 8.4799(9) _cell_length_c 12.1497(13) _cell_angle_alpha 90.00 _cell_angle_beta 106.293(2) _cell_angle_gamma 90.00 _cell_volume 1020.49(19) _cell_formula_units_Z 4 _cell_measurement_temperature 133(2) _cell_measurement_reflns_used 6178 _cell_measurement_theta_min 2.40 _cell_measurement_theta_max 30.53 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.300 _exptl_crystal_size_mid 0.300 _exptl_crystal_size_min 0.100 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.089 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 368 _exptl_absorpt_coefficient_mu 0.068 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 133(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1000 CCD' _diffrn_measurement_method \w-scan _diffrn_detector ' CCD plate ' _diffrn_detector_area_resol_mean 8.192 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 11493 _diffrn_reflns_av_R_equivalents 0.0786 _diffrn_reflns_av_sigmaI/netI 0.0516 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 30.56 _reflns_number_total 3121 _reflns_number_gt 2329 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1998)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'PLATON (Spek, 2003)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(Fo^2^)+(0.0349P)^2^+3.7145P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 3121 _refine_ls_number_parameters 120 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0693 _refine_ls_R_factor_gt 0.0496 _refine_ls_wR_factor_ref 0.1279 _refine_ls_wR_factor_gt 0.1191 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags N1 N Uani 0.34884(12) -0.05765(12) 0.03273(8) 1.000 0.0299(3) . . N2 N Uani 0.24949(8) -0.16692(10) 0.17239(7) 1.000 0.0219(2) . . N3 N Uani 0.46820(8) -0.19695(9) 0.20402(7) 1.000 0.0202(2) . . C1 C Uani 0.35519(10) -0.13373(11) 0.12681(8) 1.000 0.0192(2) . . C2 C Uani 0.29697(11) -0.25785(12) 0.27196(9) 1.000 0.0244(3) . . C3 C Uani 0.43037(11) -0.27577(12) 0.29115(8) 1.000 0.0225(3) . . C4 C Uani 0.10862(11) -0.13722(14) 0.11132(9) 1.000 0.0281(3) . . C5 C Uani 0.03069(13) -0.08165(19) 0.19291(12) 1.000 0.0464(4) . . C6 C Uani 0.04511(15) -0.28217(19) 0.04416(13) 1.000 0.0538(5) . . C7 C Uani 0.60194(10) -0.20055(12) 0.18446(9) 1.000 0.0235(3) . . C8 C Uani 0.61521(14) -0.34378(15) 0.11253(11) 1.000 0.0363(4) . . C9 C Uani 0.71140(11) -0.19448(15) 0.29834(10) 1.000 0.0334(3) . . H01A H Uiso 0.417(2) -0.053(3) 0.013(2) 0.54(2) 0.0360 . . H2 H Uiso 0.24390 -0.29940 0.31770 1.000 0.0290 calc R H3 H Uiso 0.48890 -0.33210 0.35300 1.000 0.0270 calc R H4 H Uiso 0.10640 -0.05050 0.05500 1.000 0.0340 calc R H5A H Uiso 0.02870 -0.16590 0.24760 1.000 0.0700 calc R H5B H Uiso -0.06180 -0.05480 0.14930 1.000 0.0700 calc R H5C H Uiso 0.07490 0.01170 0.23460 1.000 0.0700 calc R H6A H Uiso 0.09590 -0.31140 -0.00990 1.000 0.0810 calc R H6B H Uiso -0.04860 -0.25890 0.00180 1.000 0.0810 calc R H6C H Uiso 0.04710 -0.36970 0.09730 1.000 0.0810 calc R H7 H Uiso 0.61100 -0.10400 0.14000 1.000 0.0280 calc R H8A H Uiso 0.60950 -0.44030 0.15530 1.000 0.0540 calc R H8B H Uiso 0.70250 -0.34030 0.09540 1.000 0.0540 calc R H8C H Uiso 0.54220 -0.34280 0.04070 1.000 0.0540 calc R H9A H Uiso 0.69730 -0.10190 0.34190 1.000 0.0500 calc R H9B H Uiso 0.80010 -0.18730 0.28410 1.000 0.0500 calc R H9C H Uiso 0.70730 -0.29030 0.34240 1.000 0.0500 calc R H01B H Uiso 0.279(2) -0.017(4) 0.000(2) 0.46(2) 0.0360 . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0449(6) 0.0269(5) 0.0187(4) 0.0054(3) 0.0105(4) 0.0065(4) N2 0.0204(4) 0.0248(4) 0.0197(4) 0.0043(3) 0.0045(3) -0.0002(3) N3 0.0210(4) 0.0214(4) 0.0180(4) 0.0045(3) 0.0050(3) 0.0004(3) C1 0.0214(4) 0.0180(4) 0.0174(4) -0.0010(3) 0.0044(3) -0.0002(3) C2 0.0284(5) 0.0244(5) 0.0208(5) 0.0061(4) 0.0075(4) -0.0030(4) C3 0.0275(5) 0.0209(4) 0.0186(4) 0.0061(4) 0.0055(4) -0.0013(4) C4 0.0213(5) 0.0333(5) 0.0278(5) 0.0074(4) 0.0039(4) 0.0000(4) C5 0.0297(6) 0.0636(9) 0.0497(8) 0.0060(7) 0.0172(6) 0.0085(6) C6 0.0407(8) 0.0576(9) 0.0490(8) -0.0096(7) -0.0103(6) -0.0094(7) C7 0.0219(5) 0.0248(5) 0.0246(5) 0.0060(4) 0.0078(4) 0.0021(4) C8 0.0448(7) 0.0336(6) 0.0336(6) 0.0025(5) 0.0161(5) 0.0125(5) C9 0.0227(5) 0.0418(6) 0.0325(6) 0.0088(5) 0.0026(4) -0.0029(5) _geom_special_details ; 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. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.2981(14) . . yes N2 C1 1.3837(14) . . yes N2 C2 1.4020(13) . . yes N2 C4 1.4567(14) . . yes N3 C1 1.3833(13) . . yes N3 C3 1.3970(13) . . yes N3 C7 1.4650(14) . . yes N1 H01B 0.80(2) . . no N1 H01A 0.81(2) . . no C2 C3 1.3388(17) . . no C4 C5 1.5162(18) . . no C4 C6 1.519(2) . . no C7 C9 1.5218(16) . . no C7 C8 1.5247(17) . . no C2 H2 0.9500 . . no C3 H3 0.9500 . . no C4 H4 1.0000 . . no C5 H5A 0.9800 . . no C5 H5B 0.9800 . . no C5 H5C 0.9800 . . no C6 H6A 0.9800 . . no C6 H6B 0.9800 . . no C6 H6C 0.9800 . . no C7 H7 1.0000 . . no C8 H8A 0.9800 . . no C8 H8B 0.9800 . . no C8 H8C 0.9800 . . no C9 H9A 0.9800 . . no C9 H9B 0.9800 . . no C9 H9C 0.9800 . . no loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N2 C2 109.47(8) . . . yes C1 N2 C4 123.17(8) . . . yes C2 N2 C4 126.29(9) . . . yes C1 N3 C3 109.73(8) . . . yes C1 N3 C7 123.46(8) . . . yes C3 N3 C7 126.10(8) . . . yes C1 N1 H01A 117.0(17) . . . no C1 N1 H01B 118.0(17) . . . no N1 C1 N2 127.07(10) . . . yes N1 C1 N3 127.91(10) . . . yes N2 C1 N3 105.01(8) . . . yes N2 C2 C3 107.82(9) . . . yes N3 C3 C2 107.82(9) . . . yes N2 C4 C6 110.63(10) . . . yes C5 C4 C6 112.01(11) . . . no N2 C4 C5 110.93(9) . . . yes C8 C7 C9 112.64(10) . . . no N3 C7 C8 110.47(9) . . . yes N3 C7 C9 110.15(9) . . . yes N2 C2 H2 126.00 . . . no C3 C2 H2 126.00 . . . no N3 C3 H3 126.00 . . . no C2 C3 H3 126.00 . . . no N2 C4 H4 108.00 . . . no C5 C4 H4 108.00 . . . no C6 C4 H4 108.00 . . . no C4 C5 H5A 109.00 . . . no C4 C5 H5B 109.00 . . . no C4 C5 H5C 109.00 . . . no H5A C5 H5B 109.00 . . . no H5A C5 H5C 109.00 . . . no H5B C5 H5C 109.00 . . . no C4 C6 H6A 109.00 . . . no C4 C6 H6B 109.00 . . . no C4 C6 H6C 109.00 . . . no H6A C6 H6B 109.00 . . . no H6A C6 H6C 109.00 . . . no H6B C6 H6C 109.00 . . . no N3 C7 H7 108.00 . . . no C8 C7 H7 108.00 . . . no C9 C7 H7 108.00 . . . no C7 C8 H8A 109.00 . . . no C7 C8 H8B 109.00 . . . no C7 C8 H8C 109.00 . . . no H8A C8 H8B 109.00 . . . no H8A C8 H8C 109.00 . . . no H8B C8 H8C 109.00 . . . no C7 C9 H9A 109.00 . . . no C7 C9 H9B 109.00 . . . no C7 C9 H9C 109.00 . . . no H9A C9 H9B 109.00 . . . no H9A C9 H9C 109.00 . . . no H9B C9 H9C 109.00 . . . no _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.314 _refine_diff_density_min -0.275 _refine_diff_density_rms 0.051 #============================================================================= # end of cif data for "dpet13x" (compound 3c in manuscript) #============================================================================= #============================================================================= # cif data for "sran10x" (compound 4 in manuscript) #============================================================================= data_sran10x _database_code_depnum_ccdc_archive 'CCDC 618035' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety 'C15 H33 N3 Si2' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C15 H33 N3 Si2' _chemical_formula_weight 311.62 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall '-P 2ync' _symmetry_space_group_name_H-M 'P 21/n' loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 1/2-x,1/2+y,1/2-z 3 -x,-y,-z 4 1/2+x,1/2-y,1/2+z _cell_length_a 11.259(2) _cell_length_b 9.8467(18) _cell_length_c 18.752(3) _cell_angle_alpha 90 _cell_angle_beta 103.035(6) _cell_angle_gamma 90 _cell_volume 2025.4(6) _cell_formula_units_Z 4 _cell_measurement_temperature 133 _cell_measurement_reflns_used 5943 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 30.01 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.022 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 0.172 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 133(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1000 CCD' _diffrn_measurement_method \w-scan _diffrn_detector ' CCD plate ' _diffrn_detector_area_resol_mean 8.192 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 17512 _diffrn_reflns_av_R_equivalents 0.0727 _diffrn_reflns_av_sigmaI/netI 0.0493 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 26.37 _reflns_number_total 4145 _reflns_number_gt 3184 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1998)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'PLATON (Spek, 2003)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(Fo^2^)+(0.0349P)^2^+3.7145P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment 'rigid methyls, other riding' _refine_ls_extinction_method none _refine_ls_number_reflns 4145 _refine_ls_number_parameters 191 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0807 _refine_ls_R_factor_gt 0.0633 _refine_ls_wR_factor_ref 0.1581 _refine_ls_wR_factor_gt 0.1509 _refine_ls_goodness_of_fit_ref 1.127 _refine_ls_restrained_S_all 1.127 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags Si1 Si Uani 0.66488(9) 0.82684(9) 0.38510(5) 1.000 0.0344(3) . . Si2 Si Uani 0.87465(8) 0.34861(9) 0.65342(4) 1.000 0.0291(3) . . N1 N Uani 0.7393(2) 0.7092(2) 0.44182(13) 1.000 0.0273(8) . . N2 N Uani 0.8150(2) 0.5703(2) 0.54574(12) 1.000 0.0202(7) . . N3 N Uani 0.6735(2) 0.4807(2) 0.45921(12) 1.000 0.0231(7) . . C1 C Uani 0.7406(2) 0.5993(3) 0.47788(14) 1.000 0.0210(8) . . C2 C Uani 0.7977(3) 0.4365(3) 0.56710(15) 1.000 0.0230(8) . . C3 C Uani 0.7107(3) 0.3839(3) 0.51277(15) 1.000 0.0260(8) . . C4 C Uani 0.9008(3) 0.6682(3) 0.58890(15) 1.000 0.0241(8) . . C5 C Uani 1.0055(3) 0.6983(4) 0.55225(18) 1.000 0.0388(11) . . C6 C Uani 0.8374(3) 0.7949(3) 0.60721(19) 1.000 0.0424(11) . . C7 C Uani 0.5865(3) 0.4629(3) 0.38901(15) 1.000 0.0268(8) . . C8 C Uani 0.6508(3) 0.4132(4) 0.33116(18) 1.000 0.0456(13) . . C9 C Uani 0.4824(3) 0.3704(4) 0.39656(18) 1.000 0.0381(10) . . C10 C Uani 0.6101(4) 0.7737(5) 0.28707(19) 1.000 0.0575(15) . . C11 C Uani 0.5316(5) 0.8878(7) 0.4190(3) 1.000 0.104(3) . . C12 C Uani 0.7706(5) 0.9716(4) 0.3832(3) 1.000 0.0717(18) . . C13 C Uani 0.8180(4) 0.4210(5) 0.73155(19) 1.000 0.0506(13) . . C14 C Uani 0.8340(4) 0.1655(4) 0.6400(2) 1.000 0.0605(15) . . C15 C Uani 1.0437(3) 0.3635(3) 0.67155(18) 1.000 0.0374(10) . . H3 H Uiso 0.67970 0.29400 0.51150 1.000 0.0310 calc R H4 H Uiso 0.93740 0.62280 0.63650 1.000 0.0290 calc R H5A H Uiso 1.04430 0.61300 0.54300 1.000 0.0580 calc R H5B H Uiso 1.06550 0.75620 0.58440 1.000 0.0580 calc R H5C H Uiso 0.97410 0.74530 0.50570 1.000 0.0580 calc R H6A H Uiso 0.80340 0.84520 0.56210 1.000 0.0630 calc R H6B H Uiso 0.89620 0.85230 0.64050 1.000 0.0630 calc R H6C H Uiso 0.77150 0.76910 0.63090 1.000 0.0630 calc R H7 H Uiso 0.55100 0.55400 0.37320 1.000 0.0320 calc R H8A H Uiso 0.71930 0.47350 0.32950 1.000 0.0680 calc R H8B H Uiso 0.59340 0.41300 0.28330 1.000 0.0680 calc R H8C H Uiso 0.68120 0.32080 0.34320 1.000 0.0680 calc R H9A H Uiso 0.51320 0.27790 0.40740 1.000 0.0570 calc R H9B H Uiso 0.42000 0.37060 0.35070 1.000 0.0570 calc R H9C H Uiso 0.44670 0.40310 0.43650 1.000 0.0570 calc R H10A H Uiso 0.67690 0.72950 0.27020 1.000 0.0870 calc R H10B H Uiso 0.58300 0.85390 0.25680 1.000 0.0870 calc R H10C H Uiso 0.54200 0.71010 0.28300 1.000 0.0870 calc R H11A H Uiso 0.46970 0.81610 0.41270 1.000 0.1550 calc R H11B H Uiso 0.49710 0.96830 0.39120 1.000 0.1550 calc R H11C H Uiso 0.55760 0.91110 0.47100 1.000 0.1550 calc R H12A H Uiso 0.79170 1.01430 0.43160 1.000 0.1080 calc R H12B H Uiso 0.73080 1.03840 0.34680 1.000 0.1080 calc R H12C H Uiso 0.84490 0.93820 0.37020 1.000 0.1080 calc R H13A H Uiso 0.83520 0.51870 0.73520 1.000 0.0760 calc R H13B H Uiso 0.85930 0.37630 0.77710 1.000 0.0760 calc R H13C H Uiso 0.72990 0.40620 0.72340 1.000 0.0760 calc R H14A H Uiso 0.74590 0.15450 0.63430 1.000 0.0910 calc R H14B H Uiso 0.87710 0.11360 0.68250 1.000 0.0910 calc R H14C H Uiso 0.85760 0.13220 0.59590 1.000 0.0910 calc R H15A H Uiso 1.07170 0.33460 0.62810 1.000 0.0560 calc R H15B H Uiso 1.08070 0.30560 0.71310 1.000 0.0560 calc R H15C H Uiso 1.06750 0.45820 0.68290 1.000 0.0560 calc R loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Si1 0.0396(5) 0.0293(5) 0.0313(5) 0.0107(4) 0.0015(4) 0.0032(4) Si2 0.0355(5) 0.0255(4) 0.0239(4) 0.0073(3) 0.0017(3) -0.0017(4) N1 0.0320(14) 0.0247(13) 0.0219(12) 0.0040(10) -0.0008(10) -0.0041(11) N2 0.0241(12) 0.0183(11) 0.0173(11) 0.0006(9) 0.0027(9) -0.0020(9) N3 0.0264(13) 0.0231(12) 0.0182(11) -0.0023(9) 0.0020(10) -0.0017(10) C1 0.0235(14) 0.0235(14) 0.0157(13) -0.0020(11) 0.0040(11) 0.0005(11) C2 0.0300(15) 0.0179(13) 0.0212(13) 0.0005(11) 0.0063(11) 0.0000(11) C3 0.0318(16) 0.0195(14) 0.0259(14) -0.0010(11) 0.0050(12) -0.0030(12) C4 0.0295(15) 0.0216(14) 0.0191(13) 0.0004(11) 0.0014(11) -0.0038(12) C5 0.0343(18) 0.048(2) 0.0329(17) -0.0043(15) 0.0054(14) -0.0157(16) C6 0.052(2) 0.0319(18) 0.0378(19) -0.0146(15) -0.0013(16) 0.0021(16) C7 0.0262(15) 0.0294(15) 0.0210(14) -0.0034(12) -0.0027(12) -0.0023(12) C8 0.046(2) 0.064(3) 0.0269(17) -0.0165(17) 0.0087(15) -0.0113(18) C9 0.0288(16) 0.050(2) 0.0323(17) -0.0072(15) 0.0001(13) -0.0098(15) C10 0.071(3) 0.062(3) 0.0296(18) 0.0174(18) -0.0095(18) -0.009(2) C11 0.096(4) 0.132(5) 0.095(4) 0.054(4) 0.047(3) 0.079(4) C12 0.098(4) 0.038(2) 0.066(3) 0.023(2) -0.009(3) -0.025(2) C13 0.055(2) 0.071(3) 0.0286(18) 0.0119(18) 0.0155(17) 0.004(2) C14 0.068(3) 0.0305(19) 0.068(3) 0.0219(19) -0.016(2) -0.0100(19) C15 0.0374(18) 0.0341(18) 0.0361(17) 0.0050(15) -0.0011(14) 0.0062(14) _geom_special_details ; 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. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag Si1 N1 1.665(2) . . yes Si1 C10 1.877(4) . . yes Si1 C11 1.857(6) . . yes Si1 C12 1.863(5) . . yes Si2 C2 1.867(3) . . yes Si2 C13 1.866(4) . . yes Si2 C14 1.863(4) . . yes Si2 C15 1.862(4) . . yes N1 C1 1.274(4) . . yes N2 C1 1.386(3) . . yes N2 C2 1.403(4) . . yes N2 C4 1.471(4) . . yes N3 C1 1.392(3) . . yes N3 C3 1.380(4) . . yes N3 C7 1.463(4) . . yes C2 C3 1.347(4) . . no C4 C5 1.522(5) . . no C4 C6 1.515(4) . . no C7 C8 1.515(5) . . no C7 C9 1.516(5) . . no C3 H3 0.9500 . . no C4 H4 1.0000 . . no C5 H5A 0.9800 . . no C5 H5B 0.9800 . . no C5 H5C 0.9800 . . no C6 H6A 0.9800 . . no C6 H6B 0.9800 . . no C6 H6C 0.9800 . . no C7 H7 1.0000 . . no C8 H8A 0.9800 . . no C8 H8B 0.9800 . . no C8 H8C 0.9800 . . no C9 H9A 0.9800 . . no C9 H9B 0.9800 . . no C9 H9C 0.9800 . . no C10 H10A 0.9800 . . no C10 H10B 0.9800 . . no C10 H10C 0.9800 . . no C11 H11A 0.9800 . . no C11 H11B 0.9800 . . no C11 H11C 0.9800 . . no C12 H12A 0.9800 . . no C12 H12B 0.9800 . . no C12 H12C 0.9800 . . no C13 H13A 0.9800 . . no C13 H13B 0.9800 . . no C13 H13C 0.9800 . . no C14 H14A 0.9800 . . no C14 H14B 0.9800 . . no C14 H14C 0.9800 . . no C15 H15A 0.9800 . . no C15 H15B 0.9800 . . no C15 H15C 0.9800 . . no loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Si1 C10 116.01(17) . . . yes N1 Si1 C11 109.6(2) . . . yes N1 Si1 C12 108.23(19) . . . yes C10 Si1 C11 108.3(2) . . . yes C10 Si1 C12 105.4(2) . . . yes C11 Si1 C12 109.2(3) . . . yes C2 Si2 C13 109.24(17) . . . yes C2 Si2 C14 106.24(15) . . . yes C2 Si2 C15 112.15(15) . . . yes C13 Si2 C14 111.0(2) . . . yes C13 Si2 C15 110.05(17) . . . yes C14 Si2 C15 108.10(17) . . . yes Si1 N1 C1 150.9(2) . . . yes C1 N2 C2 111.2(2) . . . yes C1 N2 C4 123.8(2) . . . yes C2 N2 C4 125.1(2) . . . yes C1 N3 C3 109.8(2) . . . yes C1 N3 C7 122.8(2) . . . yes C3 N3 C7 127.2(2) . . . yes N1 C1 N2 126.5(2) . . . yes N1 C1 N3 129.7(2) . . . yes N2 C1 N3 103.9(2) . . . yes Si2 C2 N2 128.0(2) . . . yes Si2 C2 C3 126.4(2) . . . yes N2 C2 C3 105.6(2) . . . yes N3 C3 C2 109.5(3) . . . yes N2 C4 C5 111.0(2) . . . yes N2 C4 C6 112.3(3) . . . yes C5 C4 C6 113.2(3) . . . no N3 C7 C8 110.6(3) . . . yes N3 C7 C9 111.3(2) . . . yes C8 C7 C9 112.2(3) . . . no N3 C3 H3 125.00 . . . no C2 C3 H3 125.00 . . . no N2 C4 H4 107.00 . . . no C5 C4 H4 107.00 . . . no C6 C4 H4 107.00 . . . no C4 C5 H5A 110.00 . . . no C4 C5 H5B 109.00 . . . no C4 C5 H5C 109.00 . . . no H5A C5 H5B 110.00 . . . no H5A C5 H5C 109.00 . . . no H5B C5 H5C 109.00 . . . no C4 C6 H6A 109.00 . . . no C4 C6 H6B 110.00 . . . no C4 C6 H6C 109.00 . . . no H6A C6 H6B 110.00 . . . no H6A C6 H6C 109.00 . . . no H6B C6 H6C 109.00 . . . no N3 C7 H7 108.00 . . . no C8 C7 H7 108.00 . . . no C9 C7 H7 108.00 . . . no C7 C8 H8A 110.00 . . . no C7 C8 H8B 109.00 . . . no C7 C8 H8C 109.00 . . . no H8A C8 H8B 109.00 . . . no H8A C8 H8C 109.00 . . . no H8B C8 H8C 109.00 . . . no C7 C9 H9A 109.00 . . . no C7 C9 H9B 109.00 . . . no C7 C9 H9C 109.00 . . . no H9A C9 H9B 110.00 . . . no H9A C9 H9C 109.00 . . . no H9B C9 H9C 109.00 . . . no Si1 C10 H10A 109.00 . . . no Si1 C10 H10B 109.00 . . . no Si1 C10 H10C 109.00 . . . no H10A C10 H10B 109.00 . . . no H10A C10 H10C 110.00 . . . no H10B C10 H10C 110.00 . . . no Si1 C11 H11A 109.00 . . . no Si1 C11 H11B 109.00 . . . no Si1 C11 H11C 109.00 . . . no H11A C11 H11B 109.00 . . . no H11A C11 H11C 109.00 . . . no H11B C11 H11C 109.00 . . . no Si1 C12 H12A 109.00 . . . no Si1 C12 H12B 109.00 . . . no Si1 C12 H12C 109.00 . . . no H12A C12 H12B 110.00 . . . no H12A C12 H12C 109.00 . . . no H12B C12 H12C 110.00 . . . no Si2 C13 H13A 109.00 . . . no Si2 C13 H13B 109.00 . . . no Si2 C13 H13C 110.00 . . . no H13A C13 H13B 109.00 . . . no H13A C13 H13C 110.00 . . . no H13B C13 H13C 109.00 . . . no Si2 C14 H14A 109.00 . . . no Si2 C14 H14B 110.00 . . . no Si2 C14 H14C 109.00 . . . no H14A C14 H14B 110.00 . . . no H14A C14 H14C 109.00 . . . no H14B C14 H14C 109.00 . . . no Si2 C15 H15A 109.00 . . . no Si2 C15 H15B 109.00 . . . no Si2 C15 H15C 109.00 . . . no H15A C15 H15B 109.00 . . . no H15A C15 H15C 109.00 . . . no H15B C15 H15C 110.00 . . . no _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.393 _refine_diff_density_min -0.284 _refine_diff_density_rms 0.064 #============================================================================= # end of cif data for "sran10x" (compound 4 in manuscript) #============================================================================= #============================================================================= # end of cif file #=============================================================================