# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2004 data_global #=============================================================================== _audit_creation_date 21-11-03 _journal_coden_Cambridge 182 loop_ _publ_author_name 'Lutz H. Gade' 'Aline Maisse-Francois' 'Philip Mountford' 'Benjamin D. Ward' _publ_contact_author_name 'Prof Lutz H Gade' _publ_contact_author_address ; Institut fur Anorganische Chemie Universitat Heidelberg Im Neuenheimer Feld 270 69120 HEIDELBERG 69120 GERMANY ; _publ_contact_author_email LUTZ.GADE@UNI-HD.DE _publ_requested_journal 'Chemical Communications' _publ_section_title ; Synthesis and Structural Characterization of an Azatitanacyclobutene: The Key Intermediate in the Catalytic Anti-Markovnikov Addition of Primary Amines to a-Alkynes ; _publ_section_references ; Burla, M.C., Camalli, M., Cascarano, G.,Giacovazzo, C., Polidori, G., Spagna, R. &Viterbo, D. (1989). SIR. J. Appl. Cryst. 22, 389-393. OpenMoleN, Interactive Intelligent Structure solution (1997) Nonius B.V., Delft, The Netherlands. KappaCCD Operation Manual (1997), Nonius B.V., Delft, The Nederlands. Otwinowski, Z. & Minor, W. (1997), Methods in Enzymology, 276, 307-326. Walker, N. & Stuart, D. (1983). Acta Cryst., A39, 158-166. ; data_st1475 _database_code_depnum_ccdc_archive 'CCDC 227108' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety 'C36 H54 N4 Si2 Ti' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C36 H54 N4 Si2 Ti' _chemical_formula_weight 646.93 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C ? 0.002 0.002 International_Tables_Vol_IV_Table_2.3.1 H ? 0.000 0.000 International_Tables_Vol_IV_Table_2.3.1 N ? 0.004 0.003 International_Tables_Vol_IV_Table_2.3.1 Si ? 0.072 0.071 International_Tables_Vol_IV_Table_2.3.1 Ti ? 0.248 0.446 International_Tables_Vol_IV_Table_2.3.1 #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,1/2+y,1/2-z -x,-y,-z +x,1/2-y,1/2+z _cell_length_a 9.9150(2) _cell_length_b 20.6148(4) _cell_length_c 18.9685(5) _cell_angle_alpha 90 _cell_angle_beta 104.045(5) _cell_angle_gamma 90 _cell_volume 3761.2(1) _cell_formula_units_Z 4 _cell_measurement_temperature 173 _cell_measurement_reflns_used 11205 _cell_measurement_theta_min 1.4 _cell_measurement_theta_max 30.0 _cell_special_details ; Cell parameters refined using Scalepack part of DENZO Z. Otwinowski, W. Minor, 1997 ; _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.14 _exptl_crystal_density_method none _exptl_crystal_F_000 1392 _exptl_absorpt_coefficient_mu 0.320 _exptl_absorpt_correction_type refdelf_(Walker_&_Stuart,_1983) _exptl_absorpt_correction_T_min 0.938 _exptl_absorpt_correction_T_max 0.987 #=============================================================================== # 7. EXPERIMENTAL DATA _diffrn_special_details ; ? ; _diffrn_ambient_temperature 173 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type Mo-K\a _diffrn_source xray_tube _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method '\p scans' _diffrn_measurement_details ; 11205 reflections were collected using program Collect ("Collect" Data collection software, Nonius B.V., 1998) The conditions were as follow : crystal to detector distance = 30. mm. Scan angle = 1.6 deg 1 scans of 60 sec per frame. Data collection was divided into 2 set(s) with the following starting angles and number of frames : Set 1 Theta = 8.80 Omega = 0.00 Kappa = 0.00 121 frames Set 2 Theta = -6.90 Kappa = -166.00 Phi = 0.00 30 frames Friedel pairs were averaged. Internal R = 0.05 ; _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 11205 _diffrn_reflns_av_R_equivalents 0.050 _diffrn_reflns_av_sigmaI/netI 0.333 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.5 _diffrn_reflns_theta_max 29.99 _reflns_number_total 11205 _reflns_number_gt 4494 _reflns_threshold_expression >3.0\s(I) _computing_structure_solution Direct_methods_(SIR,_Burla_et_al.,_1989) _computing_structure_refinement LSFM_OpenMoleN_(_1997) _computing_molecular_graphics ? _computing_publication_material CIFGEN_IN_OpenMoleN_(_1997) #=============================================================================== # 8. REFINEMENT DATA _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme sigma _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method none _refine_ls_extinction_expression ? _refine_ls_extinction_coef ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 4494 _refine_ls_number_parameters 388 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_all 0.117 _refine_ls_R_factor_gt 0.054 _refine_ls_wR_factor_all 0.189 _refine_ls_wR_factor_ref 0.071 _refine_ls_goodness_of_fit_all 1.187 _refine_ls_goodness_of_fit_ref 1.262 _refine_ls_shift/su_max 0.002 _refine_ls_shift/esd_mean 0.000 _refine_diff_density_max 0.323 _refine_diff_density_min -0.136 #=============================================================================== # 9. ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_calc_attached_atom _atom_site_type_symbol TI 0.54197(6) 0.01653(3) 0.74824(3) 0.0263(3) Uani ? ? Ti C1 0.2864(4) -0.0093(2) 0.8041(2) 0.037(2) Uani ? ? C C2 0.1633(4) -0.0345(2) 0.8320(2) 0.053(2) Uani ? ? C C3 0.2776(3) -0.0414(2) 0.7293(2) 0.039(2) Uani ? ? C N1 0.3713(3) -0.0146(1) 0.6877(1) 0.031(1) Uani ? ? N SI1 0.3042(1) 0.00751(5) 0.59797(5) 0.0354(5) Uani ? ? Si C4 0.2611(4) -0.0650(2) 0.5388(2) 0.059(3) Uani ? ? C C5 0.1452(4) 0.0577(2) 0.5918(2) 0.059(3) Uani ? ? C C6 0.4367(4) 0.0573(2) 0.5688(2) 0.052(2) Uani ? ? C C7 0.4196(4) -0.0318(2) 0.8597(2) 0.043(2) Uani ? ? C N2 0.5487(3) -0.0306(1) 0.8350(1) 0.034(1) Uani ? ? N SI2 0.6713(1) -0.08743(5) 0.87915(6) 0.0417(6) Uani ? ? Si C8 0.6150(6) -0.1694(2) 0.8414(3) 0.089(4) Uani ? ? C C9 0.6803(5) -0.0852(2) 0.9780(2) 0.071(3) Uani ? ? C C10 0.8457(4) -0.0716(3) 0.8651(3) 0.079(3) Uani ? ? C C11 0.2843(3) 0.0641(2) 0.7964(2) 0.035(2) Uani ? ? C C12 0.1754(4) 0.1030(2) 0.8058(2) 0.049(2) Uani ? ? C C13 0.1800(4) 0.1693(2) 0.7957(2) 0.062(2) Uani ? ? C C14 0.2923(4) 0.1958(2) 0.7765(2) 0.057(2) Uani ? ? C C15 0.3979(4) 0.1550(2) 0.7680(2) 0.045(2) Uani ? ? C N3 0.3958(3) 0.0908(1) 0.7782(1) 0.034(1) Uani ? ? N N4 0.6918(3) 0.0881(1) 0.7505(1) 0.034(1) Uani ? ? N C16 0.7575(3) 0.0443(1) 0.7161(2) 0.029(2) Uani ? ? C C17 0.6939(3) -0.0143(1) 0.7011(2) 0.031(2) Uani ? ? C C18 0.7323(3) -0.0678(1) 0.6598(2) 0.027(2) Uani ? ? C C19 0.6414(3) -0.1210(1) 0.6410(2) 0.034(2) Uani ? ? C C20 0.6702(4) -0.1715(2) 0.5990(2) 0.042(2) Uani ? ? C C21 0.7902(4) -0.1726(2) 0.5747(2) 0.044(2) Uani ? ? C C22 0.8188(5) -0.2278(2) 0.5274(3) 0.078(3) Uani ? ? C C23 0.8810(4) -0.1213(2) 0.5934(2) 0.045(2) Uani ? ? C C24 0.8522(3) -0.0703(2) 0.6346(2) 0.037(2) Uani ? ? C C25 0.7436(3) 0.1511(1) 0.7694(2) 0.033(2) Uani ? ? C C26 0.7682(4) 0.1953(1) 0.7169(2) 0.037(2) Uani ? ? C C27 0.7439(4) 0.1794(2) 0.6366(2) 0.044(2) Uani ? ? C C28 0.8764(5) 0.1878(2) 0.6099(3) 0.072(3) Uani ? ? C C29 0.6257(5) 0.2184(2) 0.5908(2) 0.061(3) Uani ? ? C C30 0.8125(4) 0.2579(2) 0.7398(2) 0.054(2) Uani ? ? C C31 0.8300(5) 0.2767(2) 0.8109(2) 0.057(3) Uani ? ? C C32 0.8043(4) 0.2342(2) 0.8610(2) 0.056(2) Uani ? ? C C33 0.7636(4) 0.1708(2) 0.8431(2) 0.042(2) Uani ? ? C C34 0.7487(4) 0.1236(2) 0.9017(2) 0.049(2) Uani ? ? C C35 0.6565(7) 0.1477(3) 0.9485(3) 0.110(4) Uani ? ? C C36 0.8899(6) 0.1060(3) 0.9479(3) 0.094(4) Uani ? ? C H1 0.1657 -0.0157 0.8780 0.0699 Uiso calc C2 H H2 0.0787 -0.0232 0.7986 0.0699 Uiso calc C2 H H3 0.1694 -0.0804 0.8368 0.0699 Uiso calc C2 H H4 0.1850 -0.0368 0.7009 0.0517 Uiso calc C3 H H5 0.2987 -0.0862 0.7373 0.0517 Uiso calc C3 H H6 0.2246 -0.0517 0.4900 0.0811 Uiso calc C4 H H7 0.3428 -0.0901 0.5418 0.0811 Uiso calc C4 H H8 0.1939 -0.0905 0.5544 0.0811 Uiso calc C4 H H9 0.1077 0.0700 0.5427 0.0807 Uiso calc C5 H H10 0.0781 0.0331 0.6087 0.0807 Uiso calc C5 H H11 0.1686 0.0954 0.6210 0.0807 Uiso calc C5 H H12 0.4021 0.0700 0.5196 0.0692 Uiso calc C6 H H13 0.4567 0.0948 0.5986 0.0692 Uiso calc C6 H H14 0.5192 0.0325 0.5732 0.0692 Uiso calc C6 H H15 0.4050 -0.0751 0.8732 0.0558 Uiso calc C7 H H16 0.4323 -0.0044 0.9011 0.0558 Uiso calc C7 H H17 0.6806 -0.2010 0.8648 0.1274 Uiso calc C8 H H18 0.5264 -0.1793 0.8495 0.1274 Uiso calc C8 H H19 0.6095 -0.1698 0.7907 0.1274 Uiso calc C8 H H20 0.7468 -0.1160 1.0024 0.1015 Uiso calc C9 H H21 0.7070 -0.0431 0.9964 0.1015 Uiso calc C9 H H22 0.5917 -0.0955 0.9859 0.1015 Uiso calc C9 H H23 0.9088 -0.1035 0.8900 0.1254 Uiso calc C10 H H24 0.8423 -0.0733 0.8147 0.1254 Uiso calc C10 H H25 0.8762 -0.0299 0.8835 0.1254 Uiso calc C10 H H26 0.0979 0.0840 0.8191 0.0661 Uiso calc C12 H H27 0.1060 0.1962 0.8021 0.0806 Uiso calc C13 H H28 0.2977 0.2412 0.7692 0.0750 Uiso calc C14 H H29 0.4756 0.1734 0.7543 0.0594 Uiso calc C15 H H30 0.8422 0.0542 0.7035 0.0386 Uiso calc C16 H H31 0.5585 -0.1221 0.6576 0.0456 Uiso calc C19 H H32 0.6057 -0.2062 0.5866 0.0575 Uiso calc C20 H H33 0.9056 -0.2208 0.5157 0.1032 Uiso calc C22 H H34 0.8216 -0.2676 0.5529 0.1032 Uiso calc C22 H H35 0.7470 -0.2295 0.4839 0.1032 Uiso calc C22 H H36 0.9650 -0.1211 0.5777 0.0586 Uiso calc C23 H H37 0.9169 -0.0356 0.6460 0.0495 Uiso calc C24 H H38 0.8577 0.1775 0.5596 0.0915 Uiso calc C28 H H39 0.9075 0.2314 0.6171 0.0915 Uiso calc C28 H H40 0.9464 0.1596 0.6363 0.0915 Uiso calc C28 H H41 0.6137 0.2072 0.5411 0.0862 Uiso calc C29 H H42 0.5426 0.2093 0.6055 0.0862 Uiso calc C29 H H43 0.6464 0.2634 0.5971 0.0862 Uiso calc C29 H H44 0.8309 0.2881 0.7054 0.0772 Uiso calc C30 H H45 0.8600 0.3196 0.8251 0.0871 Uiso calc C31 H H46 0.8147 0.2484 0.9097 0.0787 Uiso calc C32 H H47 0.6515 0.1159 0.9840 0.1464 Uiso calc C35 H H48 0.6937 0.1867 0.9719 0.1464 Uiso calc C35 H H49 0.5659 0.1557 0.9190 0.1464 Uiso calc C35 H H50 0.8798 0.0763 0.9846 0.1305 Uiso calc C36 H H51 0.9437 0.0866 0.9184 0.1305 Uiso calc C36 H H52 0.9354 0.1441 0.9699 0.1305 Uiso calc C36 H H53 0.7178 0.1350 0.6311 0.0600 Uiso calc C27 H H54 0.7043 0.0861 0.8774 0.0670 Uiso calc C34 H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 _atom_site_aniso_type_symbol TI 0.0246(3) 0.0291(3) 0.0254(3) -0.0029(2) 0.0066(2) -0.0005(3) Ti C1 0.030(2) 0.050(2) 0.035(2) -0.001(2) 0.007(2) 0.004(2) C C2 0.037(2) 0.075(2) 0.053(2) -0.001(2) 0.018(2) 0.014(2) C C3 0.031(2) 0.047(2) 0.041(2) -0.006(2) 0.007(2) -0.003(2) C N1 0.025(1) 0.038(1) 0.033(1) -0.005(1) 0.008(1) -0.003(1) N SI1 0.0302(5) 0.0511(5) 0.0289(5) -0.0033(4) 0.0032(4) -0.0001(5) Si C4 0.060(3) 0.081(3) 0.043(2) -0.018(2) 0.005(2) -0.015(2) C C5 0.045(2) 0.086(3) 0.053(3) 0.013(2) 0.009(2) 0.021(2) C C6 0.045(2) 0.064(2) 0.048(2) -0.006(2) 0.007(2) 0.016(2) C C7 0.042(2) 0.054(2) 0.036(2) 0.003(2) 0.016(2) 0.006(2) C N2 0.028(1) 0.043(1) 0.032(2) -0.002(1) 0.010(1) 0.003(1) N SI2 0.0347(5) 0.0577(6) 0.0361(6) 0.0069(5) 0.0108(5) 0.0152(5) Si C8 0.133(4) 0.053(2) 0.099(4) 0.026(3) 0.013(4) 0.004(3) C C9 0.071(3) 0.124(4) 0.041(2) 0.032(3) 0.016(2) 0.027(3) C C10 0.035(2) 0.168(4) 0.085(3) 0.024(3) 0.013(2) 0.069(3) C C11 0.029(2) 0.057(2) 0.026(2) 0.006(2) 0.005(2) -0.001(2) C C12 0.033(2) 0.072(2) 0.048(2) 0.008(2) 0.010(2) -0.005(2) C C13 0.061(2) 0.070(2) 0.056(3) 0.027(2) 0.015(2) -0.010(2) C C14 0.062(3) 0.046(2) 0.065(3) 0.010(2) 0.014(2) -0.008(2) C C15 0.043(2) 0.040(2) 0.052(2) 0.004(2) 0.008(2) -0.004(2) C N3 0.031(1) 0.039(1) 0.034(2) 0.001(1) 0.007(1) -0.005(1) N N4 0.032(1) 0.034(1) 0.037(2) -0.006(1) 0.011(1) -0.006(1) N C16 0.022(2) 0.038(2) 0.029(2) 0.001(1) 0.005(1) 0.005(1) C C17 0.030(2) 0.031(1) 0.031(2) -0.004(1) 0.007(1) 0.001(1) C C18 0.025(2) 0.035(2) 0.023(2) 0.003(1) -0.000(1) 0.003(1) C C19 0.034(2) 0.031(2) 0.039(2) -0.001(1) 0.006(2) 0.002(2) C C20 0.051(2) 0.034(2) 0.040(2) 0.001(2) -0.001(2) -0.002(2) C C21 0.055(2) 0.040(2) 0.039(2) 0.018(2) 0.003(2) -0.002(2) C C22 0.093(3) 0.068(2) 0.076(3) 0.024(2) 0.018(3) -0.028(2) C C23 0.039(2) 0.054(2) 0.043(2) 0.016(2) 0.011(2) 0.001(2) C C24 0.030(2) 0.043(2) 0.040(2) 0.000(1) 0.006(2) -0.002(2) C C25 0.026(2) 0.034(2) 0.039(2) 0.001(1) -0.002(2) -0.006(2) C C26 0.040(2) 0.030(2) 0.042(2) 0.001(1) 0.003(2) -0.000(2) C C27 0.058(2) 0.034(2) 0.044(2) -0.005(2) 0.009(2) 0.008(2) C C28 0.077(3) 0.064(2) 0.076(3) -0.017(2) 0.031(2) -0.008(2) C C29 0.083(3) 0.052(2) 0.052(3) 0.002(2) -0.007(2) 0.008(2) C C30 0.070(3) 0.037(2) 0.060(3) -0.007(2) -0.005(2) 0.005(2) C C31 0.080(3) 0.033(2) 0.072(3) -0.004(2) -0.014(3) -0.016(2) C C32 0.075(3) 0.052(2) 0.045(2) -0.003(2) -0.003(2) -0.019(2) C C33 0.037(2) 0.048(2) 0.041(2) -0.003(2) 0.004(2) -0.013(2) C C34 0.054(2) 0.068(2) 0.033(2) -0.013(2) 0.011(2) -0.014(2) C C35 0.131(5) 0.150(5) 0.068(3) -0.007(4) 0.046(3) -0.016(4) C C36 0.083(4) 0.128(4) 0.078(3) -0.014(3) -0.004(3) 0.055(3) C # 10. MOLECULAR GEOMETRY 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 TI N1 1.911(3) . . ? TI N2 1.898(3) . . ? TI N3 2.273(3) . . ? TI N4 2.087(3) . . ? TI C16 2.428(3) . . ? TI C17 2.031(4) . . ? C1 C2 1.535(5) . . ? C1 C3 1.550(5) . . ? C1 C7 1.548(5) . . ? C1 C11 1.519(5) . . ? C3 N1 1.465(5) . . ? N1 SI1 1.731(3) . . ? SI1 C4 1.856(4) . . ? SI1 C5 1.866(4) . . ? SI1 C6 1.854(4) . . ? C7 N2 1.466(5) . . ? N2 SI2 1.749(3) . . ? SI2 C8 1.867(5) . . ? SI2 C9 1.857(5) . . ? SI2 C10 1.841(5) . . ? C11 C12 1.390(5) . . ? C11 N3 1.352(4) . . ? C12 C13 1.383(6) . . ? C13 C14 1.366(6) . . ? C14 C15 1.382(5) . . ? C15 N3 1.338(4) . . ? N4 C16 1.368(4) . . ? N4 C25 1.409(4) . . ? C16 C17 1.362(4) . . ? C17 C18 1.456(5) . . ? C18 C19 1.408(4) . . ? C18 C24 1.385(5) . . ? C19 C20 1.382(5) . . ? C20 C21 1.377(6) . . ? C21 C22 1.518(6) . . ? C21 C23 1.378(5) . . ? C23 C24 1.380(5) . . ? C25 C26 1.414(5) . . ? C25 C33 1.423(5) . . ? C26 C27 1.520(5) . . ? C26 C30 1.399(5) . . ? C27 C28 1.528(6) . . ? C27 C29 1.509(5) . . ? C30 C31 1.373(6) . . ? C31 C32 1.362(6) . . ? C32 C33 1.385(5) . . ? C33 C34 1.511(6) . . ? C34 C35 1.506(7) . . ? C34 C36 1.505(6) . . ? loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag ? ? ? ? ? ? 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 TI N2 100.9(1) . . . ? N1 TI N3 81.4(1) . . . ? N1 TI N4 140.6(1) . . . ? N1 TI C16 129.3(1) . . . ? N1 TI C17 105.9(1) . . . ? N2 TI N3 91.1(1) . . . ? N2 TI N4 118.0(1) . . . ? N2 TI C16 119.4(1) . . . ? N2 TI C17 110.3(1) . . . ? N3 TI N4 90.7(1) . . . ? N3 TI C16 123.8(1) . . . ? N3 TI C17 155.1(1) . . . ? N4 TI C16 34.2(1) . . . ? N4 TI C17 68.3(1) . . . ? C16 TI C17 34.1(1) . . . ? C2 C1 C3 107.3(3) . . . ? C2 C1 C7 106.4(3) . . . ? C2 C1 C11 112.2(3) . . . ? C3 C1 C7 110.2(3) . . . ? C3 C1 C11 109.9(3) . . . ? C7 C1 C11 110.7(3) . . . ? C1 C3 N1 115.4(3) . . . ? C3 N1 SI1 119.1(2) . . . ? N1 SI1 C4 111.0(2) . . . ? N1 SI1 C5 108.9(2) . . . ? N1 SI1 C6 108.0(2) . . . ? C4 SI1 C5 110.0(2) . . . ? C4 SI1 C6 110.0(2) . . . ? C5 SI1 C6 108.9(2) . . . ? C1 C7 N2 116.3(3) . . . ? C7 N2 SI2 113.3(2) . . . ? N2 SI2 C8 108.3(2) . . . ? N2 SI2 C9 109.0(2) . . . ? N2 SI2 C10 112.4(2) . . . ? C8 SI2 C9 110.2(3) . . . ? C8 SI2 C10 108.0(3) . . . ? C9 SI2 C10 109.0(3) . . . ? C1 C11 C12 123.7(4) . . . ? C1 C11 N3 115.9(3) . . . ? C12 C11 N3 120.5(3) . . . ? C11 C12 C13 120.0(4) . . . ? C12 C13 C14 119.2(4) . . . ? C13 C14 C15 118.6(4) . . . ? C14 C15 N3 123.1(4) . . . ? C11 N3 C15 118.7(3) . . . ? C16 N4 C25 122.8(3) . . . ? N4 C16 C17 115.8(3) . . . ? C16 C17 C18 128.1(3) . . . ? C17 C18 C19 119.3(3) . . . ? C17 C18 C24 124.9(3) . . . ? C19 C18 C24 115.7(3) . . . ? C18 C19 C20 121.5(4) . . . ? C19 C20 C21 121.5(3) . . . ? C20 C21 C22 120.7(4) . . . ? C20 C21 C23 117.7(3) . . . ? C22 C21 C23 121.6(4) . . . ? C21 C23 C24 121.2(4) . . . ? C18 C24 C23 122.4(3) . . . ? N4 C25 C26 121.9(3) . . . ? N4 C25 C33 118.0(3) . . . ? C26 C25 C33 120.1(3) . . . ? C25 C26 C27 123.8(3) . . . ? C25 C26 C30 118.1(4) . . . ? C27 C26 C30 118.1(4) . . . ? C26 C27 C28 111.6(3) . . . ? C26 C27 C29 111.9(4) . . . ? C28 C27 C29 111.1(4) . . . ? C26 C30 C31 121.4(4) . . . ? C30 C31 C32 120.2(4) . . . ? C31 C32 C33 122.0(4) . . . ? C25 C33 C32 118.2(4) . . . ? C25 C33 C34 121.5(3) . . . ? C32 C33 C34 120.2(4) . . . ? C33 C34 C35 113.7(4) . . . ? C33 C34 C36 109.9(4) . . . ? C35 C34 C36 110.4(5) . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 29.98 _diffrn_measured_fraction_theta_full 0.998