# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email wyan@mix.wvu.edu _publ_contact_author_name 'Wuming Yan' _publ_author_name 'Xiaodong Shi' data_xs20ccd _database_code_depnum_ccdc_archive 'CCDC 851290' #TrackingRef 'xs20ccd.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H23 N3 Si' _chemical_formula_weight 381.54 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 '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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/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 16.8513(12) _cell_length_b 10.3795(8) _cell_length_c 12.6903(9) _cell_angle_alpha 90.00 _cell_angle_beta 96.6150(10) _cell_angle_gamma 90.00 _cell_volume 2204.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 8095 _cell_measurement_theta_min 2.30 _cell_measurement_theta_max 27.51 _exptl_crystal_description ? _exptl_crystal_colour colorless _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.42 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.149 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 808 _exptl_absorpt_coefficient_mu 0.120 _exptl_absorpt_correction_type semi-empirical _exptl_absorpt_correction_T_min 0.9404 _exptl_absorpt_correction_T_max 0.9696 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 14902 _diffrn_reflns_av_R_equivalents 0.0338 _diffrn_reflns_av_sigmaI/netI 0.0498 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.31 _diffrn_reflns_theta_max 27.56 _reflns_number_total 5002 _reflns_number_gt 3929 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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 'calc w=1/[\s^2^(Fo^2^)+(0.0760P)^2^+0.2277P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5002 _refine_ls_number_parameters 256 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0598 _refine_ls_R_factor_gt 0.0482 _refine_ls_wR_factor_ref 0.1464 _refine_ls_wR_factor_gt 0.1352 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Si1 Si 0.08516(2) 0.37154(5) 0.71530(3) 0.05665(16) Uani 1 1 d . . . N1 N 0.15860(7) 0.15401(12) 0.62421(9) 0.0497(3) Uani 1 1 d . . . N2 N 0.09325(8) 0.08931(15) 0.65162(11) 0.0648(4) Uani 1 1 d . . . N3 N 0.09621(9) -0.02963(15) 0.62116(12) 0.0707(4) Uani 1 1 d . . . C1 C 0.16771(8) 0.28691(14) 0.65031(10) 0.0506(3) Uani 1 1 d . . . C2 C 0.23352(9) 0.34706(15) 0.63368(12) 0.0540(3) Uani 1 1 d . . . C3 C 0.29746(8) 0.41434(14) 0.61872(11) 0.0523(3) Uani 1 1 d . . . C4 C 0.30431(9) 0.47530(14) 0.51361(11) 0.0535(3) Uani 1 1 d . . . C5 C 0.23665(10) 0.50351(17) 0.44370(13) 0.0646(4) Uani 1 1 d . . . H5 H 0.1863 0.4889 0.4646 0.078 Uiso 1 1 calc R . . C6 C 0.24286(13) 0.5525(2) 0.34425(14) 0.0776(5) Uani 1 1 d . . . H6 H 0.1968 0.5706 0.2990 0.093 Uiso 1 1 calc R . . C7 C 0.31655(14) 0.5751(2) 0.31101(14) 0.0798(5) Uani 1 1 d . . . H7 H 0.3205 0.6072 0.2434 0.096 Uiso 1 1 calc R . . C8 C 0.38397(13) 0.5494(2) 0.37880(15) 0.0845(6) Uani 1 1 d . . . H8 H 0.4340 0.5649 0.3571 0.101 Uiso 1 1 calc R . . C9 C 0.37843(10) 0.5008(2) 0.47910(13) 0.0719(5) Uani 1 1 d . . . H9 H 0.4248 0.4849 0.5243 0.086 Uiso 1 1 calc R . . C10 C 0.36551(9) 0.42087(17) 0.70487(12) 0.0574(4) Uani 1 1 d . . . C11 C 0.40567(11) 0.5352(2) 0.72971(14) 0.0770(5) Uani 1 1 d . . . H11 H 0.3901 0.6101 0.6927 0.092 Uiso 1 1 calc R . . C12 C 0.46968(14) 0.5382(3) 0.81045(18) 0.1052(9) Uani 1 1 d . . . H12 H 0.4968 0.6150 0.8268 0.126 Uiso 1 1 calc R . . C13 C 0.49252(13) 0.4284(4) 0.86544(18) 0.1089(10) Uani 1 1 d . . . H13 H 0.5356 0.4305 0.9183 0.131 Uiso 1 1 calc R . . C14 C 0.45234(14) 0.3159(3) 0.84298(18) 0.1043(8) Uani 1 1 d . . . H14 H 0.4676 0.2418 0.8814 0.125 Uiso 1 1 calc R . . C15 C 0.38899(11) 0.3113(2) 0.76322(15) 0.0780(5) Uani 1 1 d . . . H15 H 0.3619 0.2341 0.7486 0.094 Uiso 1 1 calc R . . C16 C 0.11787(15) 0.5416(2) 0.7320(2) 0.0924(6) Uani 1 1 d . . . H16A H 0.0810 0.5880 0.7702 0.139 Uiso 1 1 calc R . . H16B H 0.1194 0.5803 0.6636 0.139 Uiso 1 1 calc R . . H16C H 0.1702 0.5447 0.7709 0.139 Uiso 1 1 calc R . . C17 C -0.01009(10) 0.3611(2) 0.62556(15) 0.0779(5) Uani 1 1 d . . . H17A H -0.0289 0.2737 0.6231 0.117 Uiso 1 1 calc R . . H17B H -0.0012 0.3883 0.5556 0.117 Uiso 1 1 calc R . . H17C H -0.0493 0.4159 0.6518 0.117 Uiso 1 1 calc R . . C18 C 0.07906(11) 0.2937(2) 0.84593(12) 0.0766(5) Uani 1 1 d . . . H18A H 0.0476 0.3463 0.8874 0.115 Uiso 1 1 calc R . . H18B H 0.1318 0.2842 0.8825 0.115 Uiso 1 1 calc R . . H18C H 0.0546 0.2105 0.8353 0.115 Uiso 1 1 calc R . . C19 C 0.20471(8) 0.07152(14) 0.57283(10) 0.0481(3) Uani 1 1 d . . . C20 C 0.16442(10) -0.04587(16) 0.57222(12) 0.0587(4) Uani 1 1 d . . . C21 C 0.19463(13) -0.15557(18) 0.52699(15) 0.0740(5) Uani 1 1 d . . . H21 H 0.1685 -0.2345 0.5272 0.089 Uiso 1 1 calc R . . C22 C 0.26446(13) -0.14183(19) 0.48232(15) 0.0768(5) Uani 1 1 d . . . H22 H 0.2867 -0.2134 0.4528 0.092 Uiso 1 1 calc R . . C23 C 0.30276(11) -0.02308(18) 0.48021(13) 0.0674(4) Uani 1 1 d . . . H23 H 0.3491 -0.0175 0.4472 0.081 Uiso 1 1 calc R . . C24 C 0.27481(9) 0.08627(16) 0.52495(11) 0.0553(3) Uani 1 1 d . . . H24 H 0.3009 0.1651 0.5234 0.066 Uiso 1 1 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 0.0408(2) 0.0756(3) 0.0541(2) -0.00371(18) 0.00760(16) 0.00937(18) N1 0.0385(6) 0.0595(7) 0.0530(6) -0.0011(5) 0.0136(5) -0.0057(5) N2 0.0472(7) 0.0783(9) 0.0721(8) -0.0007(7) 0.0209(6) -0.0151(6) N3 0.0635(9) 0.0723(9) 0.0790(9) 0.0000(7) 0.0199(7) -0.0204(7) C1 0.0388(6) 0.0623(8) 0.0516(6) -0.0020(6) 0.0091(5) -0.0010(6) C2 0.0421(7) 0.0601(8) 0.0610(8) -0.0066(6) 0.0107(6) 0.0005(6) C3 0.0422(7) 0.0539(8) 0.0626(8) -0.0123(6) 0.0138(6) -0.0023(6) C4 0.0474(8) 0.0567(8) 0.0583(7) -0.0149(6) 0.0142(6) -0.0058(6) C5 0.0533(9) 0.0717(10) 0.0693(9) -0.0093(8) 0.0088(7) -0.0083(7) C6 0.0755(12) 0.0901(13) 0.0654(10) -0.0063(9) 0.0006(9) -0.0065(10) C7 0.0894(14) 0.0984(14) 0.0538(8) -0.0099(9) 0.0174(9) -0.0083(11) C8 0.0685(11) 0.1245(18) 0.0656(10) -0.0087(10) 0.0292(9) -0.0091(11) C9 0.0487(8) 0.1059(14) 0.0636(9) -0.0084(9) 0.0175(7) -0.0036(9) C10 0.0404(7) 0.0759(10) 0.0584(7) -0.0151(7) 0.0167(6) -0.0046(7) C11 0.0686(11) 0.1046(14) 0.0614(9) -0.0166(9) 0.0227(8) -0.0365(10) C12 0.0779(14) 0.173(3) 0.0691(11) -0.0393(14) 0.0287(11) -0.0646(16) C13 0.0561(12) 0.205(3) 0.0662(12) -0.0319(17) 0.0079(9) -0.0037(16) C14 0.0776(14) 0.151(2) 0.0813(13) -0.0173(14) -0.0060(11) 0.0361(16) C15 0.0630(10) 0.0886(13) 0.0811(11) -0.0160(10) 0.0020(9) 0.0172(9) C16 0.0856(14) 0.0781(13) 0.1145(16) -0.0233(12) 0.0162(12) 0.0124(11) C17 0.0476(9) 0.1114(15) 0.0732(10) 0.0095(10) 0.0009(7) 0.0124(9) C18 0.0635(10) 0.1140(15) 0.0534(8) -0.0014(9) 0.0119(7) 0.0153(10) C19 0.0428(7) 0.0583(8) 0.0432(6) 0.0001(5) 0.0055(5) -0.0023(6) C20 0.0576(9) 0.0631(9) 0.0555(7) 0.0014(7) 0.0072(6) -0.0094(7) C21 0.0860(13) 0.0588(10) 0.0767(10) -0.0086(8) 0.0079(9) -0.0086(8) C22 0.0835(13) 0.0713(11) 0.0765(11) -0.0180(9) 0.0128(9) 0.0068(9) C23 0.0605(10) 0.0810(12) 0.0631(9) -0.0113(8) 0.0170(7) 0.0058(8) C24 0.0476(8) 0.0646(9) 0.0557(7) -0.0044(6) 0.0144(6) -0.0022(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_2 _geom_bond_publ_flag Si1 C16 1.854(2) . ? Si1 C18 1.8574(17) . ? Si1 C17 1.8611(18) . ? Si1 C1 1.9107(14) . ? N1 N2 1.3686(16) . ? N1 C19 1.3707(18) . ? N1 C1 1.4227(19) . ? N2 N3 1.296(2) . ? N3 C20 1.378(2) . ? C1 C2 1.311(2) . ? C2 C3 1.316(2) . ? C3 C10 1.492(2) . ? C3 C4 1.493(2) . ? C4 C5 1.393(2) . ? C4 C9 1.396(2) . ? C5 C6 1.376(3) . ? C6 C7 1.377(3) . ? C7 C8 1.370(3) . ? C8 C9 1.382(3) . ? C10 C11 1.384(2) . ? C10 C15 1.390(3) . ? C11 C12 1.400(3) . ? C12 C13 1.368(4) . ? C13 C14 1.363(4) . ? C14 C15 1.385(3) . ? C19 C20 1.394(2) . ? C19 C24 1.3975(19) . ? C20 C21 1.397(2) . ? C21 C22 1.371(3) . ? C22 C23 1.393(3) . ? C23 C24 1.376(2) . ? 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_3 _geom_angle_publ_flag C16 Si1 C18 110.99(11) . . ? C16 Si1 C17 110.45(11) . . ? C18 Si1 C17 112.85(9) . . ? C16 Si1 C1 105.40(9) . . ? C18 Si1 C1 107.65(7) . . ? C17 Si1 C1 109.18(8) . . ? N2 N1 C19 109.34(12) . . ? N2 N1 C1 119.01(11) . . ? C19 N1 C1 131.65(11) . . ? N3 N2 N1 109.38(12) . . ? N2 N3 C20 108.27(13) . . ? C2 C1 N1 119.66(13) . . ? C2 C1 Si1 121.47(12) . . ? N1 C1 Si1 118.81(9) . . ? C1 C2 C3 176.34(16) . . ? C2 C3 C10 119.43(14) . . ? C2 C3 C4 120.18(13) . . ? C10 C3 C4 120.23(12) . . ? C5 C4 C9 117.18(15) . . ? C5 C4 C3 121.08(13) . . ? C9 C4 C3 121.67(15) . . ? C6 C5 C4 121.25(16) . . ? C5 C6 C7 120.70(18) . . ? C8 C7 C6 119.13(17) . . ? C7 C8 C9 120.66(18) . . ? C8 C9 C4 121.07(17) . . ? C11 C10 C15 118.58(17) . . ? C11 C10 C3 121.35(17) . . ? C15 C10 C3 120.06(15) . . ? C10 C11 C12 120.1(2) . . ? C13 C12 C11 120.2(2) . . ? C14 C13 C12 120.2(2) . . ? C13 C14 C15 120.3(3) . . ? C14 C15 C10 120.6(2) . . ? N1 C19 C20 104.24(12) . . ? N1 C19 C24 133.81(14) . . ? C20 C19 C24 121.92(14) . . ? N3 C20 C19 108.75(14) . . ? N3 C20 C21 130.31(16) . . ? C19 C20 C21 120.93(16) . . ? C22 C21 C20 117.11(17) . . ? C21 C22 C23 121.44(17) . . ? C24 C23 C22 122.71(17) . . ? C23 C24 C19 115.83(15) . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 27.56 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.296 _refine_diff_density_min -0.245 _refine_diff_density_rms 0.048 # Attachment 'xs26ccd.CIF' data_xs26ccd _database_code_depnum_ccdc_archive 'CCDC 851291' #TrackingRef 'xs26ccd.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H25 N3 O Si' _chemical_formula_weight 411.57 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 '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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.5226(7) _cell_length_b 10.4959(8) _cell_length_c 14.8144(12) _cell_angle_alpha 71.454(1) _cell_angle_beta 89.929(1) _cell_angle_gamma 72.667(1) _cell_volume 1192.89(16) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4719 _cell_measurement_theta_min 2.51 _cell_measurement_theta_max 27.51 _exptl_crystal_description ? _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.146 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 436 _exptl_absorpt_coefficient_mu 0.118 _exptl_absorpt_correction_type semi-empirical _exptl_absorpt_correction_T_min 0.9543 _exptl_absorpt_correction_T_max 0.9883 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 8527 _diffrn_reflns_av_R_equivalents 0.0293 _diffrn_reflns_av_sigmaI/netI 0.0455 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 27.52 _reflns_number_total 5346 _reflns_number_gt 4005 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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 'calc w=1/[\s^2^(Fo^2^)+(0.0796P)^2^+0.1133P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5346 _refine_ls_number_parameters 275 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0664 _refine_ls_R_factor_gt 0.0516 _refine_ls_wR_factor_ref 0.1586 _refine_ls_wR_factor_gt 0.1444 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Si1 Si 0.31589(9) 0.23189(6) 0.12235(4) 0.0819(2) Uani 1 1 d . . . O1 O 0.31903(16) 0.60222(13) 0.37994(9) 0.0724(3) Uani 1 1 d . . . N1 N 0.30186(14) 0.17506(12) 0.32521(9) 0.0516(3) Uani 1 1 d . . . N2 N 0.22977(18) 0.07818(14) 0.31846(11) 0.0650(4) Uani 1 1 d . . . N3 N 0.19489(19) 0.01380(15) 0.40230(12) 0.0724(4) Uani 1 1 d . . . C1 C 0.24391(19) 0.06744(17) 0.46692(13) 0.0605(4) Uani 1 1 d . . . C2 C 0.2308(3) 0.0342(2) 0.56504(15) 0.0796(5) Uani 1 1 d . . . H2B H 0.1813 -0.0329 0.5974 0.096 Uiso 1 1 calc R . . C3 C 0.2935(3) 0.1039(3) 0.61123(15) 0.0868(6) Uani 1 1 d . . . H3B H 0.2888 0.0826 0.6769 0.104 Uiso 1 1 calc R . . C4 C 0.3653(3) 0.2076(2) 0.56241(14) 0.0816(5) Uani 1 1 d . . . H4A H 0.4071 0.2527 0.5968 0.098 Uiso 1 1 calc R . . C5 C 0.3756(2) 0.2442(2) 0.46571(12) 0.0651(4) Uani 1 1 d . . . H5A H 0.4216 0.3139 0.4334 0.078 Uiso 1 1 calc R . . C6 C 0.31334(16) 0.17114(15) 0.41848(11) 0.0514(3) Uani 1 1 d . . . C7 C 0.33779(18) 0.26653(16) 0.23898(11) 0.0531(3) Uani 1 1 d . . . C8 C 0.37621(18) 0.37746(16) 0.24069(11) 0.0530(3) Uani 1 1 d . . . C9 C 0.41277(17) 0.49217(15) 0.23699(10) 0.0496(3) Uani 1 1 d . . . C10 C 0.58680(18) 0.48930(16) 0.25388(11) 0.0537(3) Uani 1 1 d . . . C11 C 0.7116(2) 0.3634(2) 0.2901(2) 0.0900(7) Uani 1 1 d . . . H11A H 0.6877 0.2789 0.3031 0.108 Uiso 1 1 calc R . . C12 C 0.8721(3) 0.3598(3) 0.3074(3) 0.1235(11) Uani 1 1 d . . . H12A H 0.9548 0.2732 0.3326 0.148 Uiso 1 1 calc R . . C13 C 0.9105(3) 0.4826(3) 0.2878(2) 0.1089(9) Uani 1 1 d . . . H13A H 1.0189 0.4799 0.2990 0.131 Uiso 1 1 calc R . . C14 C 0.7893(3) 0.6080(3) 0.25205(18) 0.0902(7) Uani 1 1 d . . . H14A H 0.8148 0.6920 0.2384 0.108 Uiso 1 1 calc R . . C15 C 0.6269(2) 0.6125(2) 0.23553(14) 0.0693(5) Uani 1 1 d . . . H15A H 0.5445 0.6995 0.2119 0.083 Uiso 1 1 calc R . . C16 C 0.27648(18) 0.62888(15) 0.21836(11) 0.0531(3) Uani 1 1 d . . . C17 C 0.1909(2) 0.70376(19) 0.12839(13) 0.0707(5) Uani 1 1 d . . . H17A H 0.2179 0.6685 0.0783 0.085 Uiso 1 1 calc R . . C18 C 0.0655(3) 0.8307(2) 0.11219(17) 0.0852(6) Uani 1 1 d . . . H18A H 0.0082 0.8797 0.0517 0.102 Uiso 1 1 calc R . . C19 C 0.0266(2) 0.8834(2) 0.18564(18) 0.0820(6) Uani 1 1 d . . . H19A H -0.0560 0.9695 0.1742 0.098 Uiso 1 1 calc R . . C20 C 0.1075(2) 0.81108(19) 0.27586(15) 0.0695(5) Uani 1 1 d . . . H20A H 0.0793 0.8477 0.3253 0.083 Uiso 1 1 calc R . . C21 C 0.23175(19) 0.68301(16) 0.29294(12) 0.0568(4) Uani 1 1 d . . . C22 C 0.2584(3) 0.6344(2) 0.46253(15) 0.0899(6) Uani 1 1 d . . . H22A H 0.3261 0.5654 0.5189 0.135 Uiso 1 1 calc R . . H22B H 0.1466 0.6328 0.4662 0.135 Uiso 1 1 calc R . . H22C H 0.2619 0.7268 0.4581 0.135 Uiso 1 1 calc R . . C23 C 0.4224(4) 0.0434(3) 0.1355(2) 0.1206(10) Uani 1 1 d . . . H23A H 0.4037 0.0279 0.0765 0.181 Uiso 1 1 calc R . . H23B H 0.3796 -0.0165 0.1858 0.181 Uiso 1 1 calc R . . H23C H 0.5389 0.0215 0.1510 0.181 Uiso 1 1 calc R . . C24 C 0.0905(4) 0.2799(4) 0.0862(2) 0.1379(12) Uani 1 1 d . . . H24A H 0.0749 0.2755 0.0233 0.207 Uiso 1 1 calc R . . H24B H 0.0353 0.3742 0.0861 0.207 Uiso 1 1 calc R . . H24C H 0.0452 0.2148 0.1308 0.207 Uiso 1 1 calc R . . C25 C 0.4066(6) 0.3529(4) 0.0349(2) 0.1614(16) Uani 1 1 d . . . H25A H 0.3964 0.3424 -0.0266 0.242 Uiso 1 1 calc R . . H25B H 0.5213 0.3303 0.0556 0.242 Uiso 1 1 calc R . . H25C H 0.3492 0.4488 0.0305 0.242 Uiso 1 1 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 0.1322(5) 0.0773(4) 0.0574(3) -0.0318(3) 0.0066(3) -0.0530(3) O1 0.0856(8) 0.0709(7) 0.0588(7) -0.0303(6) 0.0018(6) -0.0123(6) N1 0.0568(6) 0.0475(6) 0.0573(7) -0.0204(5) 0.0039(5) -0.0230(5) N2 0.0780(8) 0.0529(7) 0.0761(9) -0.0249(7) 0.0045(7) -0.0340(7) N3 0.0843(10) 0.0559(8) 0.0827(10) -0.0182(7) 0.0106(8) -0.0351(7) C1 0.0589(8) 0.0494(8) 0.0676(10) -0.0132(7) 0.0064(7) -0.0159(7) C2 0.0852(12) 0.0683(11) 0.0734(12) -0.0085(9) 0.0190(10) -0.0232(9) C3 0.0970(14) 0.0967(15) 0.0569(10) -0.0181(10) 0.0154(10) -0.0241(12) C4 0.0937(13) 0.0969(14) 0.0643(11) -0.0364(10) 0.0083(10) -0.0342(12) C5 0.0733(10) 0.0737(10) 0.0595(9) -0.0284(8) 0.0085(8) -0.0325(8) C6 0.0478(7) 0.0495(7) 0.0562(8) -0.0181(6) 0.0046(6) -0.0136(6) C7 0.0608(8) 0.0520(8) 0.0542(8) -0.0212(7) 0.0038(6) -0.0252(7) C8 0.0593(8) 0.0563(8) 0.0516(8) -0.0229(6) 0.0064(6) -0.0244(7) C9 0.0602(8) 0.0513(7) 0.0453(7) -0.0188(6) 0.0078(6) -0.0259(6) C10 0.0600(8) 0.0575(8) 0.0544(8) -0.0245(7) 0.0148(6) -0.0279(7) C11 0.0606(10) 0.0675(11) 0.143(2) -0.0342(12) 0.0119(11) -0.0227(9) C12 0.0558(11) 0.0970(17) 0.214(3) -0.050(2) 0.0128(15) -0.0204(11) C13 0.0591(11) 0.132(2) 0.164(3) -0.071(2) 0.0307(14) -0.0462(14) C14 0.0816(13) 0.1009(16) 0.1250(19) -0.0575(14) 0.0347(13) -0.0605(13) C15 0.0736(10) 0.0685(10) 0.0843(12) -0.0340(9) 0.0187(9) -0.0396(9) C16 0.0593(8) 0.0501(8) 0.0570(8) -0.0169(6) 0.0034(6) -0.0282(6) C17 0.0865(11) 0.0622(10) 0.0617(10) -0.0134(8) -0.0060(8) -0.0286(9) C18 0.0955(14) 0.0602(11) 0.0853(14) -0.0042(10) -0.0233(11) -0.0249(10) C19 0.0714(11) 0.0513(9) 0.1160(17) -0.0199(10) -0.0077(11) -0.0174(8) C20 0.0659(9) 0.0590(9) 0.0919(13) -0.0334(9) 0.0088(9) -0.0226(8) C21 0.0586(8) 0.0525(8) 0.0652(9) -0.0218(7) 0.0044(7) -0.0236(7) C22 0.1225(17) 0.0859(14) 0.0679(12) -0.0387(11) 0.0170(11) -0.0279(13) C23 0.167(3) 0.110(2) 0.114(2) -0.0762(17) 0.0305(19) -0.0433(19) C24 0.166(3) 0.132(2) 0.111(2) -0.0348(18) -0.061(2) -0.048(2) C25 0.302(5) 0.181(3) 0.0794(17) -0.066(2) 0.077(2) -0.164(4) _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_2 _geom_bond_publ_flag Si1 C25 1.851(3) . ? Si1 C23 1.860(3) . ? Si1 C24 1.867(3) . ? Si1 C7 1.8955(15) . ? O1 C21 1.366(2) . ? O1 C22 1.427(2) . ? N1 N2 1.3633(16) . ? N1 C6 1.3721(19) . ? N1 C7 1.4287(19) . ? N2 N3 1.293(2) . ? N3 C1 1.376(2) . ? C1 C6 1.391(2) . ? C1 C2 1.395(3) . ? C2 C3 1.357(3) . ? C3 C4 1.406(3) . ? C4 C5 1.370(3) . ? C5 C6 1.394(2) . ? C7 C8 1.3075(19) . ? C8 C9 1.316(2) . ? C9 C10 1.494(2) . ? C9 C16 1.497(2) . ? C10 C11 1.370(3) . ? C10 C15 1.380(2) . ? C11 C12 1.379(3) . ? C12 C13 1.365(4) . ? C13 C14 1.352(4) . ? C14 C15 1.390(3) . ? C16 C17 1.386(2) . ? C16 C21 1.399(2) . ? C17 C18 1.387(3) . ? C18 C19 1.369(3) . ? C19 C20 1.372(3) . ? C20 C21 1.389(2) . ? 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_3 _geom_angle_publ_flag C25 Si1 C23 111.90(17) . . ? C25 Si1 C24 110.05(19) . . ? C23 Si1 C24 110.39(15) . . ? C25 Si1 C7 105.33(10) . . ? C23 Si1 C7 111.40(11) . . ? C24 Si1 C7 107.57(12) . . ? C21 O1 C22 118.19(15) . . ? N2 N1 C6 109.52(12) . . ? N2 N1 C7 118.24(12) . . ? C6 N1 C7 131.99(12) . . ? N3 N2 N1 109.15(13) . . ? N2 N3 C1 108.60(13) . . ? N3 C1 C6 108.62(15) . . ? N3 C1 C2 130.27(16) . . ? C6 C1 C2 121.11(17) . . ? C3 C2 C1 117.10(18) . . ? C2 C3 C4 121.75(19) . . ? C5 C4 C3 121.98(19) . . ? C4 C5 C6 116.26(16) . . ? N1 C6 C1 104.11(13) . . ? N1 C6 C5 134.12(14) . . ? C1 C6 C5 121.77(15) . . ? C8 C7 N1 119.49(13) . . ? C8 C7 Si1 120.88(12) . . ? N1 C7 Si1 119.51(10) . . ? C7 C8 C9 176.68(16) . . ? C8 C9 C10 121.86(14) . . ? C8 C9 C16 119.40(13) . . ? C10 C9 C16 118.72(12) . . ? C11 C10 C15 117.76(15) . . ? C11 C10 C9 120.84(14) . . ? C15 C10 C9 121.39(15) . . ? C10 C11 C12 121.2(2) . . ? C13 C12 C11 120.4(2) . . ? C14 C13 C12 119.40(19) . . ? C13 C14 C15 120.51(19) . . ? C10 C15 C14 120.69(19) . . ? C17 C16 C21 118.52(15) . . ? C17 C16 C9 121.50(15) . . ? C21 C16 C9 119.97(13) . . ? C16 C17 C18 120.79(19) . . ? C19 C18 C17 119.70(19) . . ? C18 C19 C20 120.98(18) . . ? C19 C20 C21 119.65(18) . . ? O1 C21 C20 124.38(16) . . ? O1 C21 C16 115.29(14) . . ? C20 C21 C16 120.33(16) . . ? _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 27.52 _diffrn_measured_fraction_theta_full 0.974 _refine_diff_density_max 0.287 _refine_diff_density_min -0.140 _refine_diff_density_rms 0.042 # Attachment 'xs37ccd.cif' data_xs37ccd _database_code_depnum_ccdc_archive 'CCDC 851292' #TrackingRef 'xs37ccd.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H17 N3 O' _chemical_formula_weight 339.39 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 '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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/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 9.8385(8) _cell_length_b 11.9791(10) _cell_length_c 15.5682(13) _cell_angle_alpha 90.00 _cell_angle_beta 93.823(1) _cell_angle_gamma 90.00 _cell_volume 1830.7(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6766 _cell_measurement_theta_min 2.52 _cell_measurement_theta_max 25.47 _exptl_crystal_description ? _exptl_crystal_colour light _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.231 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 712 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type semi-empirical _exptl_absorpt_correction_T_min 0.9667 _exptl_absorpt_correction_T_max 0.9786 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 11967 _diffrn_reflns_av_R_equivalents 0.0344 _diffrn_reflns_av_sigmaI/netI 0.0595 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.68 _diffrn_reflns_theta_max 27.54 _reflns_number_total 4128 _reflns_number_gt 3192 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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 'calc w=1/[\s^2^(Fo^2^)+(0.0792P)^2^+0.2414P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4128 _refine_ls_number_parameters 236 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0662 _refine_ls_R_factor_gt 0.0533 _refine_ls_wR_factor_ref 0.1687 _refine_ls_wR_factor_gt 0.1550 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.92285(15) 0.78913(14) -0.01247(8) 0.0876(5) Uani 1 1 d . . . N1 N 0.44583(15) 1.12986(13) 0.18062(12) 0.0746(4) Uani 1 1 d . . . N2 N 0.47958(14) 1.03855(13) 0.22123(10) 0.0685(4) Uani 1 1 d . . . N3 N 0.57598(11) 0.98410(10) 0.17740(8) 0.0506(3) Uani 1 1 d . . . C1 C 0.51914(15) 1.13697(13) 0.10842(11) 0.0584(4) Uani 1 1 d . . . C2 C 0.51695(19) 1.21791(14) 0.04380(14) 0.0726(5) Uani 1 1 d . . . H2 H 0.4602 1.2799 0.0449 0.087 Uiso 1 1 calc R . . C3 C 0.6016(2) 1.20203(16) -0.02101(14) 0.0782(5) Uani 1 1 d . . . H3 H 0.6029 1.2546 -0.0649 0.094 Uiso 1 1 calc R . . C4 C 0.6867(2) 1.10841(16) -0.02303(12) 0.0740(5) Uani 1 1 d . . . H4 H 0.7433 1.1011 -0.0682 0.089 Uiso 1 1 calc R . . C5 C 0.68972(16) 1.02727(14) 0.03913(10) 0.0582(4) Uani 1 1 d . . . H5 H 0.7458 0.9650 0.0370 0.070 Uiso 1 1 calc R . . C6 C 0.60352(13) 1.04369(11) 0.10586(9) 0.0478(3) Uani 1 1 d . . . C7 C 0.62628(13) 0.88102(13) 0.20925(9) 0.0508(3) Uani 1 1 d . . . H7 H 0.5864 0.8498 0.2561 0.061 Uiso 1 1 calc R . . C8 C 0.72521(14) 0.82704(12) 0.17684(9) 0.0484(3) Uani 1 1 d . . . C9 C 0.82463(12) 0.77017(11) 0.14590(8) 0.0434(3) Uani 1 1 d . . . C10 C 0.79390(13) 0.68432(11) 0.07810(9) 0.0468(3) Uani 1 1 d . . . C11 C 0.70823(16) 0.59544(13) 0.09238(12) 0.0607(4) Uani 1 1 d . . . H11 H 0.6683 0.5897 0.1447 0.073 Uiso 1 1 calc R . . C12 C 0.6814(2) 0.51529(16) 0.02999(16) 0.0850(6) Uani 1 1 d . . . H12 H 0.6245 0.4555 0.0403 0.102 Uiso 1 1 calc R . . C13 C 0.7393(2) 0.5245(2) -0.04743(18) 0.0972(7) Uani 1 1 d . . . H13 H 0.7230 0.4694 -0.0889 0.117 Uiso 1 1 calc R . . C14 C 0.8212(2) 0.6139(2) -0.06504(14) 0.0903(7) Uani 1 1 d . . . H14 H 0.8578 0.6201 -0.1184 0.108 Uiso 1 1 calc R . . C15 C 0.84853(16) 0.69499(15) -0.00196(10) 0.0633(4) Uani 1 1 d . . . C16 C 0.9703(4) 0.8117(3) -0.09495(17) 0.1552(16) Uani 1 1 d . . . H16A H 1.0383 0.7578 -0.1076 0.233 Uiso 1 1 calc R . . H16B H 1.0091 0.8852 -0.0952 0.233 Uiso 1 1 calc R . . H16C H 0.8955 0.8074 -0.1377 0.233 Uiso 1 1 calc R . . C17 C 0.96836(13) 0.78806(12) 0.17983(8) 0.0459(3) Uani 1 1 d . . . C18 C 1.01073(17) 0.89113(15) 0.21142(11) 0.0640(4) Uani 1 1 d . . . H18 H 0.9502 0.9508 0.2086 0.077 Uiso 1 1 calc R . . C19 C 1.14137(19) 0.9065(2) 0.24694(14) 0.0836(6) Uani 1 1 d . . . H19 H 1.1688 0.9765 0.2673 0.100 Uiso 1 1 calc R . . C20 C 1.23110(17) 0.8189(2) 0.25239(13) 0.0819(6) Uani 1 1 d . . . H20 H 1.3188 0.8290 0.2773 0.098 Uiso 1 1 calc R . . C21 C 1.19107(17) 0.71624(19) 0.22089(12) 0.0737(5) Uani 1 1 d . . . H21 H 1.2518 0.6567 0.2247 0.088 Uiso 1 1 calc R . . C22 C 1.06049(15) 0.70057(15) 0.18331(10) 0.0580(4) Uani 1 1 d . . . H22 H 1.0349 0.6314 0.1605 0.070 Uiso 1 1 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 O1 0.1003(9) 0.1165(12) 0.0483(7) -0.0093(7) 0.0223(6) -0.0444(8) N1 0.0689(8) 0.0675(9) 0.0883(11) -0.0129(8) 0.0128(8) 0.0176(7) N2 0.0626(8) 0.0725(9) 0.0730(9) -0.0113(7) 0.0230(7) 0.0123(7) N3 0.0459(6) 0.0546(7) 0.0523(7) -0.0066(5) 0.0109(5) 0.0034(5) C1 0.0533(7) 0.0491(8) 0.0720(10) -0.0110(7) -0.0033(7) 0.0011(6) C2 0.0753(10) 0.0474(9) 0.0921(13) -0.0023(8) -0.0175(10) 0.0030(8) C3 0.0953(13) 0.0596(11) 0.0777(12) 0.0146(9) -0.0099(11) -0.0114(9) C4 0.0851(11) 0.0728(12) 0.0648(10) 0.0091(9) 0.0108(9) -0.0053(9) C5 0.0617(8) 0.0582(9) 0.0554(8) 0.0008(7) 0.0093(7) 0.0016(7) C6 0.0444(6) 0.0467(7) 0.0518(7) -0.0064(6) -0.0009(5) -0.0035(5) C7 0.0499(7) 0.0566(8) 0.0468(7) -0.0002(6) 0.0089(6) -0.0008(6) C8 0.0500(7) 0.0533(8) 0.0420(7) 0.0012(6) 0.0021(5) 0.0002(6) C9 0.0478(6) 0.0453(7) 0.0371(6) 0.0045(5) 0.0036(5) 0.0004(5) C10 0.0466(6) 0.0459(7) 0.0472(7) 0.0004(6) -0.0016(5) 0.0027(5) C11 0.0611(8) 0.0515(9) 0.0683(10) 0.0089(7) -0.0051(7) -0.0047(7) C12 0.0892(13) 0.0543(10) 0.1086(17) -0.0066(10) -0.0139(12) -0.0141(9) C13 0.1035(15) 0.0783(14) 0.1079(18) -0.0427(13) -0.0066(13) -0.0082(12) C14 0.0890(13) 0.1149(18) 0.0679(12) -0.0384(12) 0.0103(10) -0.0066(12) C15 0.0605(8) 0.0785(11) 0.0514(8) -0.0145(8) 0.0074(7) -0.0097(8) C16 0.177(3) 0.229(4) 0.0642(14) -0.0135(19) 0.0487(17) -0.103(3) C17 0.0474(6) 0.0554(8) 0.0352(6) 0.0016(5) 0.0042(5) -0.0010(6) C18 0.0625(8) 0.0654(10) 0.0638(9) -0.0086(8) 0.0007(7) -0.0054(7) C19 0.0713(11) 0.0949(15) 0.0834(13) -0.0210(11) -0.0046(9) -0.0215(11) C20 0.0514(8) 0.1259(18) 0.0674(11) -0.0061(11) -0.0032(8) -0.0119(10) C21 0.0512(8) 0.1052(15) 0.0645(10) 0.0048(10) 0.0019(7) 0.0150(9) C22 0.0537(7) 0.0665(10) 0.0534(8) -0.0003(7) 0.0025(6) 0.0073(7) _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_2 _geom_bond_publ_flag O1 C15 1.360(2) . ? O1 C16 1.421(2) . ? N1 N2 1.295(2) . ? N1 C1 1.378(2) . ? N2 N3 1.3700(16) . ? N3 C6 1.3652(19) . ? N3 C7 1.4081(19) . ? C1 C6 1.394(2) . ? C1 C2 1.396(3) . ? C2 C3 1.364(3) . ? C3 C4 1.401(3) . ? C4 C5 1.371(2) . ? C5 C6 1.398(2) . ? C7 C8 1.2983(19) . ? C8 C9 1.3099(18) . ? C9 C10 1.4903(18) . ? C9 C17 1.4915(17) . ? C10 C11 1.385(2) . ? C10 C15 1.396(2) . ? C11 C12 1.379(3) . ? C12 C13 1.371(3) . ? C13 C14 1.379(3) . ? C14 C15 1.394(3) . ? C17 C18 1.383(2) . ? C17 C22 1.384(2) . ? C18 C19 1.377(2) . ? C19 C20 1.370(3) . ? C20 C21 1.372(3) . ? C21 C22 1.388(2) . ? 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_3 _geom_angle_publ_flag C15 O1 C16 118.58(17) . . ? N2 N1 C1 108.61(13) . . ? N1 N2 N3 108.81(14) . . ? C6 N3 N2 109.81(13) . . ? C6 N3 C7 131.43(11) . . ? N2 N3 C7 118.74(12) . . ? N1 C1 C6 108.59(15) . . ? N1 C1 C2 130.30(15) . . ? C6 C1 C2 121.10(16) . . ? C3 C2 C1 117.08(16) . . ? C2 C3 C4 121.57(17) . . ? C5 C4 C3 122.46(17) . . ? C4 C5 C6 116.06(15) . . ? N3 C6 C1 104.17(13) . . ? N3 C6 C5 134.09(13) . . ? C1 C6 C5 121.73(14) . . ? C8 C7 N3 123.70(13) . . ? C7 C8 C9 178.24(16) . . ? C8 C9 C10 119.88(12) . . ? C8 C9 C17 120.58(12) . . ? C10 C9 C17 119.52(11) . . ? C11 C10 C15 119.24(14) . . ? C11 C10 C9 120.91(13) . . ? C15 C10 C9 119.82(12) . . ? C12 C11 C10 120.80(17) . . ? C13 C12 C11 119.45(18) . . ? C12 C13 C14 121.33(19) . . ? C13 C14 C15 119.3(2) . . ? O1 C15 C14 124.94(17) . . ? O1 C15 C10 115.19(13) . . ? C14 C15 C10 119.83(17) . . ? C18 C17 C22 118.74(13) . . ? C18 C17 C9 120.68(13) . . ? C22 C17 C9 120.53(13) . . ? C19 C18 C17 120.89(17) . . ? C20 C19 C18 120.16(19) . . ? C19 C20 C21 119.74(16) . . ? C20 C21 C22 120.48(17) . . ? C17 C22 C21 119.95(16) . . ? _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 27.54 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 0.212 _refine_diff_density_min -0.206 _refine_diff_density_rms 0.037 # Attachment 'xs40ccd.cif' data_xs40ccd _database_code_depnum_ccdc_archive 'CCDC 851293' #TrackingRef 'xs40ccd.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H26 N6 Si' _chemical_formula_weight 462.63 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 '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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 12.0515(12) _cell_length_b 15.0765(15) _cell_length_c 15.9874(16) _cell_angle_alpha 114.773(2) _cell_angle_beta 92.532(2) _cell_angle_gamma 96.523(2) _cell_volume 2606.8(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.179 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 976 _exptl_absorpt_coefficient_mu 0.116 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9530 _exptl_absorpt_correction_T_max 0.9897 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18732 _diffrn_reflns_av_R_equivalents 0.0405 _diffrn_reflns_av_sigmaI/netI 0.0834 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.41 _diffrn_reflns_theta_max 27.57 _reflns_number_total 11679 _reflns_number_gt 6972 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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 'calc w=1/[\s^2^(Fo^2^)+(0.0921P)^2^+0.1459P] 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_extinction_coef ? _refine_ls_number_reflns 11679 _refine_ls_number_parameters 619 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1073 _refine_ls_R_factor_gt 0.0635 _refine_ls_wR_factor_ref 0.2013 _refine_ls_wR_factor_gt 0.1728 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Si1 Si 0.68238(6) 0.02322(5) 0.31350(5) 0.0649(2) Uani 1 1 d . . . Si2 Si 0.16716(6) 0.54822(5) 0.30806(5) 0.0701(2) Uani 1 1 d . . . N1 N 0.84404(19) 0.03313(16) 0.06835(15) 0.0815(7) Uani 1 1 d . . . N2 N 0.8542(2) 0.01687(17) -0.01825(16) 0.0888(7) Uani 1 1 d . . . N3 N 0.91513(17) 0.09689(15) -0.01754(14) 0.0689(5) Uani 1 1 d . . . N4 N 0.64034(13) 0.21425(13) 0.32775(12) 0.0546(4) Uani 1 1 d . . . N5 N 0.53763(15) 0.18875(16) 0.35100(15) 0.0711(6) Uani 1 1 d . . . N6 N 0.48217(17) 0.26240(18) 0.37330(17) 0.0808(6) Uani 1 1 d . . . N7 N 0.4199(2) 0.60441(15) -0.02165(14) 0.0815(7) Uani 1 1 d . . . N8 N 0.3447(2) 0.53448(19) -0.02336(16) 0.1014(9) Uani 1 1 d . . . N9 N 0.3358(2) 0.54853(18) 0.06288(15) 0.0974(9) Uani 1 1 d . . . N10 N 0.16588(15) 0.75005(13) 0.33518(13) 0.0601(5) Uani 1 1 d . . . N11 N 0.07177(19) 0.74420(18) 0.37849(19) 0.0916(8) Uani 1 1 d . . . N12 N 0.0344(2) 0.8282(2) 0.4090(2) 0.1055(9) Uani 1 1 d . . . C1 C 0.90126(16) 0.16475(15) 0.22704(15) 0.0517(5) Uani 1 1 d . . . C2 C 0.80610(17) 0.15754(16) 0.26313(15) 0.0564(5) Uani 1 1 d . . . C3 C 0.71510(16) 0.14262(16) 0.29924(15) 0.0538(5) Uani 1 1 d . . . C4 C 0.89923(16) 0.12380(15) 0.12509(15) 0.0547(5) Uani 1 1 d . . . C5 C 0.9455(2) 0.16357(17) 0.06985(16) 0.0682(6) Uani 1 1 d . . . H5 H 0.9894 0.2249 0.0891 0.082 Uiso 1 1 calc R . . C6 C 0.9439(3) 0.0970(2) -0.10567(19) 0.0971(10) Uani 1 1 d . . . H6A H 0.8773 0.0722 -0.1498 0.117 Uiso 1 1 calc R . . H6B H 0.9992 0.0533 -0.1304 0.117 Uiso 1 1 calc R . . C7 C 0.9898(3) 0.1988(2) -0.09383(17) 0.0776(7) Uani 1 1 d . . . C8 C 1.1039(3) 0.2312(3) -0.0747(2) 0.1004(10) Uani 1 1 d . . . H8 H 1.1516 0.1887 -0.0701 0.120 Uiso 1 1 calc R . . C9 C 1.1488(3) 0.3231(3) -0.0625(3) 0.1157(13) Uani 1 1 d . . . H9 H 1.2257 0.3437 -0.0483 0.139 Uiso 1 1 calc R . . C10 C 1.0794(4) 0.3844(3) -0.0714(3) 0.1249(15) Uani 1 1 d . . . H10 H 1.1100 0.4467 -0.0648 0.150 Uiso 1 1 calc R . . C11 C 0.9667(4) 0.3567(3) -0.0896(3) 0.1218(13) Uani 1 1 d . . . H11 H 0.9206 0.4001 -0.0947 0.146 Uiso 1 1 calc R . . C12 C 0.9201(3) 0.2627(2) -0.1008(2) 0.0966(9) Uani 1 1 d . . . H12 H 0.8428 0.2432 -0.1129 0.116 Uiso 1 1 calc R . . C13 C 1.00891(16) 0.21317(15) 0.28693(15) 0.0516(5) Uani 1 1 d . . . C14 C 1.11185(17) 0.20130(16) 0.25135(16) 0.0570(5) Uani 1 1 d . . . H14 H 1.1144 0.1639 0.1883 0.068 Uiso 1 1 calc R . . C15 C 1.21084(18) 0.24456(18) 0.30883(17) 0.0652(6) Uani 1 1 d . . . H15 H 1.2793 0.2359 0.2840 0.078 Uiso 1 1 calc R . . C16 C 1.2090(2) 0.29962(18) 0.40128(18) 0.0689(6) Uani 1 1 d . . . H16 H 1.2758 0.3286 0.4394 0.083 Uiso 1 1 calc R . . C17 C 1.1080(2) 0.3120(2) 0.43775(18) 0.0802(7) Uani 1 1 d . . . H17 H 1.1064 0.3493 0.5009 0.096 Uiso 1 1 calc R . . C18 C 1.0085(2) 0.26937(19) 0.38131(17) 0.0739(7) Uani 1 1 d . . . H18 H 0.9405 0.2784 0.4069 0.089 Uiso 1 1 calc R . . C19 C 0.64940(17) 0.30907(16) 0.33560(14) 0.0536(5) Uani 1 1 d . . . C20 C 0.7343(2) 0.37199(17) 0.32238(17) 0.0661(6) Uani 1 1 d . . . H20 H 0.8029 0.3524 0.3036 0.079 Uiso 1 1 calc R . . C21 C 0.7100(2) 0.46449(19) 0.33886(19) 0.0794(7) Uani 1 1 d . . . H21 H 0.7642 0.5085 0.3308 0.095 Uiso 1 1 calc R . . C22 C 0.6073(3) 0.4951(2) 0.36715(19) 0.0846(8) Uani 1 1 d . . . H22 H 0.5949 0.5583 0.3770 0.102 Uiso 1 1 calc R . . C23 C 0.5243(2) 0.4333(2) 0.38063(19) 0.0831(8) Uani 1 1 d . . . H23 H 0.4558 0.4532 0.3994 0.100 Uiso 1 1 calc R . . C24 C 0.54775(19) 0.33869(19) 0.36472(16) 0.0657(6) Uani 1 1 d . . . C25 C 0.5715(3) -0.0598(2) 0.2217(2) 0.1157(12) Uani 1 1 d . . . H25A H 0.5981 -0.0751 0.1622 0.173 Uiso 1 1 calc R . . H25B H 0.5060 -0.0279 0.2264 0.173 Uiso 1 1 calc R . . H25C H 0.5528 -0.1197 0.2289 0.173 Uiso 1 1 calc R . . C26 C 0.6407(3) 0.0490(3) 0.4301(2) 0.1062(11) Uani 1 1 d . . . H26A H 0.6386 -0.0097 0.4402 0.159 Uiso 1 1 calc R . . H26B H 0.5676 0.0693 0.4352 0.159 Uiso 1 1 calc R . . H26C H 0.6941 0.1006 0.4757 0.159 Uiso 1 1 calc R . . C27 C 0.8145(3) -0.0303(3) 0.2972(3) 0.1283(14) Uani 1 1 d . . . H27A H 0.8071 -0.0861 0.3118 0.192 Uiso 1 1 calc R . . H27B H 0.8748 0.0185 0.3373 0.192 Uiso 1 1 calc R . . H27C H 0.8303 -0.0510 0.2340 0.192 Uiso 1 1 calc R . . C28 C 0.41068(17) 0.66535(14) 0.22157(14) 0.0499(5) Uani 1 1 d . . . C29 C 0.31522(17) 0.67029(15) 0.26041(14) 0.0534(5) Uani 1 1 d . . . C30 C 0.22247(17) 0.66595(15) 0.29776(15) 0.0539(5) Uani 1 1 d . . . C31 C 0.40508(18) 0.62887(15) 0.11991(14) 0.0535(5) Uani 1 1 d . . . C32 C 0.4618(3) 0.66296(18) 0.06555(17) 0.0873(9) Uani 1 1 d . . . H32 H 0.5187 0.7166 0.0851 0.105 Uiso 1 1 calc R . . C33 C 0.4534(4) 0.6043(2) -0.1085(2) 0.1250(15) Uani 1 1 d . . . H33A H 0.3925 0.5692 -0.1571 0.150 Uiso 1 1 calc R . . H33B H 0.5178 0.5696 -0.1257 0.150 Uiso 1 1 calc R . . C34 C 0.4829(3) 0.70705(18) -0.10069(15) 0.0724(7) Uani 1 1 d . . . C35 C 0.5929(3) 0.7450(3) -0.0968(2) 0.1064(11) Uani 1 1 d . . . H35 H 0.6484 0.7064 -0.0985 0.128 Uiso 1 1 calc R . . C36 C 0.6231(4) 0.8363(3) -0.0905(3) 0.152(2) Uani 1 1 d . . . H36 H 0.6985 0.8601 -0.0876 0.182 Uiso 1 1 calc R . . C37 C 0.5475(7) 0.8909(4) -0.0885(3) 0.151(2) Uani 1 1 d . . . H37 H 0.5706 0.9540 -0.0837 0.181 Uiso 1 1 calc R . . C38 C 0.4374(5) 0.8616(3) -0.0929(3) 0.1331(17) Uani 1 1 d . . . H38 H 0.3850 0.9025 -0.0927 0.160 Uiso 1 1 calc R . . C39 C 0.4036(3) 0.7666(3) -0.0978(2) 0.1036(10) Uani 1 1 d . . . H39 H 0.3281 0.7445 -0.0991 0.124 Uiso 1 1 calc R . . C40 C 0.52150(17) 0.69713(14) 0.27883(14) 0.0508(5) Uani 1 1 d . . . C41 C 0.62091(18) 0.67322(17) 0.23941(16) 0.0616(6) Uani 1 1 d . . . H41 H 0.6192 0.6362 0.1758 0.074 Uiso 1 1 calc R . . C42 C 0.7230(2) 0.70450(19) 0.29477(19) 0.0726(7) Uani 1 1 d . . . H42 H 0.7889 0.6882 0.2676 0.087 Uiso 1 1 calc R . . C43 C 0.7278(2) 0.7589(2) 0.38856(19) 0.0760(7) Uani 1 1 d . . . H43 H 0.7964 0.7805 0.4249 0.091 Uiso 1 1 calc R . . C44 C 0.6296(2) 0.7812(2) 0.42834(18) 0.0780(7) Uani 1 1 d . . . H44 H 0.6318 0.8164 0.4922 0.094 Uiso 1 1 calc R . . C45 C 0.5279(2) 0.75164(18) 0.37441(16) 0.0657(6) Uani 1 1 d . . . H45 H 0.4625 0.7684 0.4024 0.079 Uiso 1 1 calc R . . C46 C 0.18904(18) 0.84314(16) 0.33885(15) 0.0574(5) Uani 1 1 d . . . C47 C 0.2732(2) 0.88996(17) 0.30846(17) 0.0698(6) Uani 1 1 d . . . H47 H 0.3307 0.8576 0.2777 0.084 Uiso 1 1 calc R . . C48 C 0.2669(3) 0.9864(2) 0.3262(2) 0.0863(8) Uani 1 1 d . . . H48 H 0.3219 1.0203 0.3071 0.104 Uiso 1 1 calc R . . C49 C 0.1813(3) 1.0353(2) 0.3717(2) 0.0923(9) Uani 1 1 d . . . H49 H 0.1795 1.1002 0.3810 0.111 Uiso 1 1 calc R . . C50 C 0.1003(3) 0.9905(2) 0.4028(2) 0.0950(9) Uani 1 1 d . . . H50 H 0.0442 1.0240 0.4346 0.114 Uiso 1 1 calc R . . C51 C 0.1042(2) 0.89174(19) 0.3852(2) 0.0768(7) Uani 1 1 d . . . C52 C 0.0187(3) 0.5043(3) 0.2576(3) 0.1457(17) Uani 1 1 d . . . H52A H -0.0065 0.4435 0.2613 0.219 Uiso 1 1 calc R . . H52B H 0.0130 0.4938 0.1939 0.219 Uiso 1 1 calc R . . H52C H -0.0271 0.5530 0.2914 0.219 Uiso 1 1 calc R . . C53 C 0.1869(4) 0.5733(3) 0.4322(3) 0.1423(17) Uani 1 1 d . . . H53A H 0.1745 0.5121 0.4380 0.213 Uiso 1 1 calc R . . H53B H 0.1343 0.6151 0.4655 0.213 Uiso 1 1 calc R . . H53C H 0.2620 0.6055 0.4574 0.213 Uiso 1 1 calc R . . C54 C 0.2544(3) 0.4568(2) 0.2392(2) 0.0982(10) Uani 1 1 d . . . H54A H 0.3319 0.4805 0.2626 0.147 Uiso 1 1 calc R . . H54B H 0.2444 0.4464 0.1757 0.147 Uiso 1 1 calc R . . H54C H 0.2325 0.3956 0.2432 0.147 Uiso 1 1 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 0.0665(4) 0.0655(4) 0.0656(4) 0.0301(3) 0.0175(3) 0.0087(3) Si2 0.0840(5) 0.0648(4) 0.0734(5) 0.0369(4) 0.0330(4) 0.0178(3) N1 0.0840(14) 0.0752(14) 0.0651(14) 0.0175(11) 0.0135(11) -0.0197(11) N2 0.0958(17) 0.0800(15) 0.0648(14) 0.0156(12) 0.0052(12) -0.0254(13) N3 0.0793(13) 0.0645(12) 0.0524(11) 0.0183(9) 0.0037(10) -0.0029(10) N4 0.0399(9) 0.0678(11) 0.0591(11) 0.0296(9) 0.0107(7) 0.0073(7) N5 0.0470(10) 0.0926(15) 0.0882(15) 0.0502(13) 0.0219(10) 0.0144(10) N6 0.0549(12) 0.1071(17) 0.0993(17) 0.0558(14) 0.0286(11) 0.0304(11) N7 0.1277(19) 0.0596(12) 0.0453(11) 0.0159(9) 0.0132(11) -0.0087(12) N8 0.125(2) 0.0943(17) 0.0561(14) 0.0168(12) 0.0072(13) -0.0355(15) N9 0.1192(19) 0.0917(16) 0.0510(13) 0.0142(11) 0.0123(12) -0.0392(14) N10 0.0529(10) 0.0601(11) 0.0688(12) 0.0261(9) 0.0193(9) 0.0142(8) N11 0.0746(14) 0.0855(15) 0.127(2) 0.0488(15) 0.0548(14) 0.0310(12) N12 0.0848(17) 0.0964(18) 0.148(3) 0.0525(18) 0.0556(17) 0.0459(14) C1 0.0437(10) 0.0537(11) 0.0579(13) 0.0236(10) 0.0108(9) 0.0064(8) C2 0.0473(11) 0.0612(13) 0.0588(13) 0.0239(11) 0.0076(9) 0.0069(9) C3 0.0424(10) 0.0634(13) 0.0543(12) 0.0250(10) 0.0063(9) 0.0029(9) C4 0.0447(11) 0.0551(12) 0.0584(13) 0.0195(10) 0.0062(9) 0.0033(9) C5 0.0845(16) 0.0571(13) 0.0521(14) 0.0179(11) 0.0042(12) -0.0090(11) C6 0.150(3) 0.0796(19) 0.0522(15) 0.0229(14) 0.0118(17) -0.0014(18) C7 0.104(2) 0.0758(17) 0.0463(13) 0.0224(12) 0.0050(13) 0.0013(15) C8 0.095(2) 0.116(3) 0.083(2) 0.0342(19) 0.0158(17) 0.0166(19) C9 0.105(3) 0.125(3) 0.101(3) 0.042(2) 0.018(2) -0.021(2) C10 0.156(4) 0.108(3) 0.109(3) 0.058(2) 0.000(3) -0.031(3) C11 0.173(4) 0.094(2) 0.099(3) 0.048(2) -0.016(3) 0.009(3) C12 0.104(2) 0.101(2) 0.075(2) 0.0340(18) -0.0158(17) 0.0005(18) C13 0.0466(11) 0.0532(11) 0.0565(12) 0.0242(10) 0.0109(9) 0.0081(8) C14 0.0462(11) 0.0700(14) 0.0566(13) 0.0293(11) 0.0102(9) 0.0044(9) C15 0.0449(12) 0.0821(16) 0.0741(17) 0.0399(14) 0.0092(11) 0.0029(10) C16 0.0575(13) 0.0738(15) 0.0720(17) 0.0322(13) -0.0052(12) -0.0033(11) C17 0.0704(16) 0.0908(19) 0.0542(15) 0.0066(13) 0.0008(12) 0.0134(13) C18 0.0549(13) 0.0866(17) 0.0615(15) 0.0118(13) 0.0127(11) 0.0143(12) C19 0.0507(11) 0.0624(13) 0.0443(11) 0.0191(10) 0.0030(9) 0.0104(9) C20 0.0623(14) 0.0646(14) 0.0673(15) 0.0250(12) 0.0050(11) 0.0062(11) C21 0.0905(19) 0.0662(16) 0.0748(18) 0.0264(14) 0.0003(14) 0.0035(14) C22 0.106(2) 0.0724(17) 0.0718(18) 0.0245(14) 0.0005(16) 0.0287(16) C23 0.0855(19) 0.095(2) 0.0736(18) 0.0328(16) 0.0131(14) 0.0434(16) C24 0.0585(13) 0.0854(17) 0.0588(14) 0.0328(13) 0.0088(11) 0.0231(12) C25 0.132(3) 0.087(2) 0.101(2) 0.0281(19) -0.003(2) -0.036(2) C26 0.148(3) 0.112(2) 0.083(2) 0.0592(19) 0.033(2) 0.036(2) C27 0.114(3) 0.112(3) 0.198(4) 0.092(3) 0.059(3) 0.049(2) C28 0.0539(11) 0.0455(10) 0.0483(11) 0.0173(9) 0.0125(9) 0.0077(8) C29 0.0578(12) 0.0499(11) 0.0513(12) 0.0194(10) 0.0103(10) 0.0099(9) C30 0.0524(11) 0.0564(12) 0.0530(12) 0.0223(10) 0.0124(9) 0.0099(9) C31 0.0596(12) 0.0479(11) 0.0480(11) 0.0162(9) 0.0097(9) 0.0040(9) C32 0.131(2) 0.0615(15) 0.0510(14) 0.0152(12) 0.0113(15) -0.0258(15) C33 0.237(5) 0.0729(19) 0.0529(17) 0.0207(14) 0.034(2) -0.008(2) C34 0.110(2) 0.0613(14) 0.0398(12) 0.0174(11) 0.0112(12) 0.0046(14) C35 0.099(2) 0.099(2) 0.092(2) 0.0073(19) 0.0262(19) 0.0274(19) C36 0.153(4) 0.107(3) 0.131(4) -0.003(3) 0.072(3) -0.039(3) C37 0.262(8) 0.094(3) 0.086(3) 0.037(2) 0.028(4) -0.012(4) C38 0.211(5) 0.098(3) 0.080(2) 0.024(2) -0.029(3) 0.060(3) C39 0.091(2) 0.114(3) 0.075(2) 0.0163(19) -0.0143(16) 0.004(2) C40 0.0543(11) 0.0465(10) 0.0517(12) 0.0203(9) 0.0131(9) 0.0072(8) C41 0.0595(13) 0.0633(13) 0.0584(13) 0.0215(11) 0.0163(10) 0.0082(10) C42 0.0535(13) 0.0841(17) 0.0843(19) 0.0393(15) 0.0150(12) 0.0095(12) C43 0.0620(15) 0.0873(18) 0.0771(18) 0.0380(15) -0.0061(13) -0.0021(12) C44 0.0768(17) 0.0901(18) 0.0542(14) 0.0209(13) -0.0010(13) 0.0050(14) C45 0.0628(14) 0.0728(15) 0.0505(13) 0.0149(11) 0.0118(11) 0.0103(11) C46 0.0592(13) 0.0561(12) 0.0532(13) 0.0194(10) 0.0002(10) 0.0117(9) C47 0.0764(16) 0.0595(14) 0.0680(16) 0.0234(12) 0.0044(12) 0.0045(11) C48 0.109(2) 0.0635(16) 0.0814(19) 0.0303(14) 0.0007(17) 0.0000(15) C49 0.127(3) 0.0618(16) 0.083(2) 0.0264(15) -0.0149(19) 0.0228(17) C50 0.100(2) 0.0784(19) 0.100(2) 0.0252(17) 0.0058(18) 0.0427(17) C51 0.0701(16) 0.0703(16) 0.0882(19) 0.0278(14) 0.0102(14) 0.0266(12) C52 0.092(2) 0.115(3) 0.237(5) 0.090(3) 0.018(3) -0.020(2) C53 0.241(5) 0.131(3) 0.094(3) 0.068(2) 0.081(3) 0.078(3) C54 0.143(3) 0.0710(17) 0.096(2) 0.0419(17) 0.050(2) 0.0358(17) _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_2 _geom_bond_publ_flag Si1 C26 1.844(3) . ? Si1 C27 1.846(3) . ? Si1 C25 1.847(3) . ? Si1 C3 1.907(2) . ? Si2 C54 1.838(3) . ? Si2 C52 1.856(4) . ? Si2 C53 1.857(4) . ? Si2 C30 1.899(2) . ? N1 N2 1.315(3) . ? N1 C4 1.355(3) . ? N2 N3 1.335(3) . ? N3 C5 1.338(3) . ? N3 C6 1.467(3) . ? N4 N5 1.368(2) . ? N4 C19 1.373(3) . ? N4 C3 1.425(3) . ? N5 N6 1.290(3) . ? N6 C24 1.379(3) . ? N7 N8 1.300(3) . ? N7 C32 1.335(3) . ? N7 C33 1.463(3) . ? N8 N9 1.316(3) . ? N9 C31 1.332(3) . ? N10 N11 1.368(3) . ? N10 C46 1.375(3) . ? N10 C30 1.424(3) . ? N11 N12 1.295(3) . ? N12 C51 1.386(3) . ? C1 C2 1.320(3) . ? C1 C4 1.479(3) . ? C1 C13 1.491(3) . ? C2 C3 1.302(3) . ? C4 C5 1.364(3) . ? C6 C7 1.500(4) . ? C7 C8 1.382(4) . ? C7 C12 1.382(4) . ? C8 C9 1.357(5) . ? C9 C10 1.360(6) . ? C10 C11 1.357(6) . ? C11 C12 1.399(5) . ? C13 C14 1.386(3) . ? C13 C18 1.387(3) . ? C14 C15 1.385(3) . ? C15 C16 1.361(3) . ? C16 C17 1.371(3) . ? C17 C18 1.381(3) . ? C19 C24 1.385(3) . ? C19 C20 1.399(3) . ? C20 C21 1.375(4) . ? C21 C22 1.397(4) . ? C22 C23 1.375(4) . ? C23 C24 1.404(4) . ? C28 C29 1.326(3) . ? C28 C31 1.477(3) . ? C28 C40 1.493(3) . ? C29 C30 1.298(3) . ? C31 C32 1.354(3) . ? C33 C34 1.500(4) . ? C34 C35 1.370(4) . ? C34 C39 1.373(5) . ? C35 C36 1.343(6) . ? C36 C37 1.288(7) . ? C37 C38 1.338(7) . ? C38 C39 1.412(5) . ? C40 C41 1.392(3) . ? C40 C45 1.393(3) . ? C41 C42 1.394(3) . ? C42 C43 1.369(4) . ? C43 C44 1.376(4) . ? C44 C45 1.381(3) . ? C46 C51 1.384(3) . ? C46 C47 1.389(3) . ? C47 C48 1.372(4) . ? C48 C49 1.388(4) . ? C49 C50 1.352(4) . ? C50 C51 1.402(4) . ? 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_3 _geom_angle_publ_flag C26 Si1 C27 110.29(18) . . ? C26 Si1 C25 111.84(17) . . ? C27 Si1 C25 110.17(19) . . ? C26 Si1 C3 110.75(13) . . ? C27 Si1 C3 105.05(12) . . ? C25 Si1 C3 108.50(13) . . ? C54 Si2 C52 108.85(18) . . ? C54 Si2 C53 111.01(17) . . ? C52 Si2 C53 112.9(2) . . ? C54 Si2 C30 105.09(11) . . ? C52 Si2 C30 110.90(14) . . ? C53 Si2 C30 107.86(15) . . ? N2 N1 C4 109.28(19) . . ? N1 N2 N3 107.50(19) . . ? N2 N3 C5 109.86(19) . . ? N2 N3 C6 119.1(2) . . ? C5 N3 C6 130.9(2) . . ? N5 N4 C19 109.60(17) . . ? N5 N4 C3 118.40(17) . . ? C19 N4 C3 131.99(16) . . ? N6 N5 N4 109.01(19) . . ? N5 N6 C24 108.45(19) . . ? N8 N7 C32 110.0(2) . . ? N8 N7 C33 119.9(2) . . ? C32 N7 C33 129.9(2) . . ? N7 N8 N9 107.4(2) . . ? N8 N9 C31 109.72(19) . . ? N11 N10 C46 109.46(18) . . ? N11 N10 C30 118.77(17) . . ? C46 N10 C30 131.76(18) . . ? N12 N11 N10 109.3(2) . . ? N11 N12 C51 108.1(2) . . ? C2 C1 C4 118.54(19) . . ? C2 C1 C13 121.3(2) . . ? C4 C1 C13 120.20(16) . . ? C3 C2 C1 174.3(2) . . ? C2 C3 N4 120.68(19) . . ? C2 C3 Si1 119.22(17) . . ? N4 C3 Si1 120.10(13) . . ? N1 C4 C5 106.9(2) . . ? N1 C4 C1 122.32(18) . . ? C5 C4 C1 130.72(19) . . ? N3 C5 C4 106.38(19) . . ? N3 C6 C7 111.5(2) . . ? C8 C7 C12 118.2(3) . . ? C8 C7 C6 120.3(3) . . ? C12 C7 C6 121.5(3) . . ? C9 C8 C7 122.1(4) . . ? C8 C9 C10 119.0(4) . . ? C11 C10 C9 121.5(4) . . ? C10 C11 C12 119.6(4) . . ? C7 C12 C11 119.5(3) . . ? C14 C13 C18 118.0(2) . . ? C14 C13 C1 121.62(19) . . ? C18 C13 C1 120.34(18) . . ? C15 C14 C13 120.6(2) . . ? C16 C15 C14 120.7(2) . . ? C15 C16 C17 119.5(2) . . ? C16 C17 C18 120.5(2) . . ? C17 C18 C13 120.7(2) . . ? N4 C19 C24 103.96(18) . . ? N4 C19 C20 134.1(2) . . ? C24 C19 C20 122.0(2) . . ? C21 C20 C19 116.0(2) . . ? C20 C21 C22 122.8(3) . . ? C23 C22 C21 121.1(3) . . ? C22 C23 C24 116.9(3) . . ? N6 C24 C19 109.0(2) . . ? N6 C24 C23 129.8(2) . . ? C19 C24 C23 121.2(2) . . ? C29 C28 C31 118.38(19) . . ? C29 C28 C40 121.15(19) . . ? C31 C28 C40 120.47(17) . . ? C30 C29 C28 174.0(2) . . ? C29 C30 N10 120.54(18) . . ? C29 C30 Si2 119.21(17) . . ? N10 C30 Si2 120.16(14) . . ? N9 C31 C32 106.3(2) . . ? N9 C31 C28 122.10(18) . . ? C32 C31 C28 131.56(19) . . ? N7 C32 C31 106.4(2) . . ? N7 C33 C34 111.9(2) . . ? C35 C34 C39 117.1(3) . . ? C35 C34 C33 120.1(3) . . ? C39 C34 C33 122.8(3) . . ? C36 C35 C34 122.1(4) . . ? C37 C36 C35 119.9(5) . . ? C36 C37 C38 123.4(5) . . ? C37 C38 C39 117.7(4) . . ? C34 C39 C38 119.7(4) . . ? C41 C40 C45 117.9(2) . . ? C41 C40 C28 121.74(19) . . ? C45 C40 C28 120.34(18) . . ? C40 C41 C42 120.3(2) . . ? C43 C42 C41 121.0(2) . . ? C42 C43 C44 119.1(2) . . ? C43 C44 C45 120.7(2) . . ? C44 C45 C40 121.0(2) . . ? N10 C46 C51 104.2(2) . . ? N10 C46 C47 134.2(2) . . ? C51 C46 C47 121.6(2) . . ? C48 C47 C46 116.4(3) . . ? C47 C48 C49 122.3(3) . . ? C50 C49 C48 121.5(3) . . ? C49 C50 C51 117.6(3) . . ? C46 C51 N12 109.0(2) . . ? C46 C51 C50 120.7(3) . . ? N12 C51 C50 130.3(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4 N1 N2 N3 -0.3(3) . . . . ? N1 N2 N3 C5 1.0(3) . . . . ? N1 N2 N3 C6 177.3(3) . . . . ? C19 N4 N5 N6 -0.3(3) . . . . ? C3 N4 N5 N6 -179.02(19) . . . . ? N4 N5 N6 C24 0.3(3) . . . . ? C32 N7 N8 N9 1.3(4) . . . . ? C33 N7 N8 N9 175.9(3) . . . . ? N7 N8 N9 C31 0.7(4) . . . . ? C46 N10 N11 N12 0.1(3) . . . . ? C30 N10 N11 N12 178.8(2) . . . . ? N10 N11 N12 C51 0.4(4) . . . . ? C4 C1 C2 C3 97(2) . . . . ? C13 C1 C2 C3 -83(2) . . . . ? C1 C2 C3 N4 172(2) . . . . ? C1 C2 C3 Si1 -9(2) . . . . ? N5 N4 C3 C2 169.5(2) . . . . ? C19 N4 C3 C2 -8.9(3) . . . . ? N5 N4 C3 Si1 -10.4(3) . . . . ? C19 N4 C3 Si1 171.17(17) . . . . ? C26 Si1 C3 C2 133.4(2) . . . . ? C27 Si1 C3 C2 14.3(2) . . . . ? C25 Si1 C3 C2 -103.5(2) . . . . ? C26 Si1 C3 N4 -46.7(2) . . . . ? C27 Si1 C3 N4 -165.8(2) . . . . ? C25 Si1 C3 N4 76.4(2) . . . . ? N2 N1 C4 C5 -0.5(3) . . . . ? N2 N1 C4 C1 178.6(2) . . . . ? C2 C1 C4 N1 -46.2(3) . . . . ? C13 C1 C4 N1 134.0(2) . . . . ? C2 C1 C4 C5 132.6(3) . . . . ? C13 C1 C4 C5 -47.2(3) . . . . ? N2 N3 C5 C4 -1.3(3) . . . . ? C6 N3 C5 C4 -177.0(3) . . . . ? N1 C4 C5 N3 1.1(3) . . . . ? C1 C4 C5 N3 -177.9(2) . . . . ? N2 N3 C6 C7 167.5(3) . . . . ? C5 N3 C6 C7 -17.2(5) . . . . ? N3 C6 C7 C8 90.8(4) . . . . ? N3 C6 C7 C12 -88.7(3) . . . . ? C12 C7 C8 C9 0.2(5) . . . . ? C6 C7 C8 C9 -179.2(3) . . . . ? C7 C8 C9 C10 -1.5(5) . . . . ? C8 C9 C10 C11 1.8(6) . . . . ? C9 C10 C11 C12 -0.8(6) . . . . ? C8 C7 C12 C11 0.8(4) . . . . ? C6 C7 C12 C11 -179.8(3) . . . . ? C10 C11 C12 C7 -0.5(5) . . . . ? C2 C1 C13 C14 164.6(2) . . . . ? C4 C1 C13 C14 -15.5(3) . . . . ? C2 C1 C13 C18 -13.3(3) . . . . ? C4 C1 C13 C18 166.5(2) . . . . ? C18 C13 C14 C15 0.0(3) . . . . ? C1 C13 C14 C15 -178.03(19) . . . . ? C13 C14 C15 C16 -0.1(3) . . . . ? C14 C15 C16 C17 0.2(4) . . . . ? C15 C16 C17 C18 -0.3(4) . . . . ? C16 C17 C18 C13 0.2(4) . . . . ? C14 C13 C18 C17 0.0(4) . . . . ? C1 C13 C18 C17 178.0(2) . . . . ? N5 N4 C19 C24 0.1(2) . . . . ? C3 N4 C19 C24 178.7(2) . . . . ? N5 N4 C19 C20 178.8(2) . . . . ? C3 N4 C19 C20 -2.7(4) . . . . ? N4 C19 C20 C21 -179.3(2) . . . . ? C24 C19 C20 C21 -0.8(3) . . . . ? C19 C20 C21 C22 0.0(4) . . . . ? C20 C21 C22 C23 0.4(4) . . . . ? C21 C22 C23 C24 0.0(4) . . . . ? N5 N6 C24 C19 -0.2(3) . . . . ? N5 N6 C24 C23 179.7(3) . . . . ? N4 C19 C24 N6 0.0(2) . . . . ? C20 C19 C24 N6 -178.8(2) . . . . ? N4 C19 C24 C23 -179.9(2) . . . . ? C20 C19 C24 C23 1.3(4) . . . . ? C22 C23 C24 N6 179.3(3) . . . . ? C22 C23 C24 C19 -0.8(4) . . . . ? C31 C28 C29 C30 93(2) . . . . ? C40 C28 C29 C30 -88(2) . . . . ? C28 C29 C30 N10 174(2) . . . . ? C28 C29 C30 Si2 -3(2) . . . . ? N11 N10 C30 C29 -176.4(2) . . . . ? C46 N10 C30 C29 1.9(4) . . . . ? N11 N10 C30 Si2 0.1(3) . . . . ? C46 N10 C30 Si2 178.43(18) . . . . ? C54 Si2 C30 C29 -10.0(2) . . . . ? C52 Si2 C30 C29 -127.5(2) . . . . ? C53 Si2 C30 C29 108.5(2) . . . . ? C54 Si2 C30 N10 173.4(2) . . . . ? C52 Si2 C30 N10 55.9(2) . . . . ? C53 Si2 C30 N10 -68.1(2) . . . . ? N8 N9 C31 C32 -2.4(4) . . . . ? N8 N9 C31 C28 177.8(2) . . . . ? C29 C28 C31 N9 -45.7(3) . . . . ? C40 C28 C31 N9 135.2(2) . . . . ? C29 C28 C31 C32 134.6(3) . . . . ? C40 C28 C31 C32 -44.6(4) . . . . ? N8 N7 C32 C31 -2.8(4) . . . . ? C33 N7 C32 C31 -176.7(3) . . . . ? N9 C31 C32 N7 3.1(3) . . . . ? C28 C31 C32 N7 -177.1(2) . . . . ? N8 N7 C33 C34 147.0(3) . . . . ? C32 N7 C33 C34 -39.6(5) . . . . ? N7 C33 C34 C35 106.7(4) . . . . ? N7 C33 C34 C39 -73.8(4) . . . . ? C39 C34 C35 C36 -0.1(5) . . . . ? C33 C34 C35 C36 179.5(3) . . . . ? C34 C35 C36 C37 -0.4(7) . . . . ? C35 C36 C37 C38 -0.4(8) . . . . ? C36 C37 C38 C39 1.5(8) . . . . ? C35 C34 C39 C38 1.2(4) . . . . ? C33 C34 C39 C38 -178.3(3) . . . . ? C37 C38 C39 C34 -1.9(6) . . . . ? C29 C28 C40 C41 165.9(2) . . . . ? C31 C28 C40 C41 -15.0(3) . . . . ? C29 C28 C40 C45 -13.6(3) . . . . ? C31 C28 C40 C45 165.46(19) . . . . ? C45 C40 C41 C42 -0.8(3) . . . . ? C28 C40 C41 C42 179.66(19) . . . . ? C40 C41 C42 C43 0.1(4) . . . . ? C41 C42 C43 C44 1.2(4) . . . . ? C42 C43 C44 C45 -1.9(4) . . . . ? C43 C44 C45 C40 1.2(4) . . . . ? C41 C40 C45 C44 0.1(3) . . . . ? C28 C40 C45 C44 179.7(2) . . . . ? N11 N10 C46 C51 -0.6(3) . . . . ? C30 N10 C46 C51 -179.0(2) . . . . ? N11 N10 C46 C47 178.7(3) . . . . ? C30 N10 C46 C47 0.3(4) . . . . ? N10 C46 C47 C48 -179.7(2) . . . . ? C51 C46 C47 C48 -0.5(4) . . . . ? C46 C47 C48 C49 -0.2(4) . . . . ? C47 C48 C49 C50 1.4(5) . . . . ? C48 C49 C50 C51 -1.7(5) . . . . ? N10 C46 C51 N12 0.9(3) . . . . ? C47 C46 C51 N12 -178.5(2) . . . . ? N10 C46 C51 C50 179.6(2) . . . . ? C47 C46 C51 C50 0.2(4) . . . . ? N11 N12 C51 C46 -0.8(4) . . . . ? N11 N12 C51 C50 -179.4(3) . . . . ? C49 C50 C51 C46 0.9(4) . . . . ? C49 C50 C51 N12 179.3(3) . . . . ? _diffrn_measured_fraction_theta_max 0.968 _diffrn_reflns_theta_full 27.57 _diffrn_measured_fraction_theta_full 0.968 _refine_diff_density_max 0.345 _refine_diff_density_min -0.231 _refine_diff_density_rms 0.042 # Attachment 'xs41ccd.cif' data_xs41ccd _database_code_depnum_ccdc_archive 'CCDC 851294' #TrackingRef 'xs41ccd.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H21 F2 N3 Si' _chemical_formula_weight 417.53 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 '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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/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 20.3557(18) _cell_length_b 11.1404(11) _cell_length_c 21.776(2) _cell_angle_alpha 90.00 _cell_angle_beta 110.508(2) _cell_angle_gamma 90.00 _cell_volume 4625.2(8) _cell_formula_units_Z 8 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 5121 _cell_measurement_theta_min 2.13 _cell_measurement_theta_max 27.11 _exptl_crystal_description 'irregular block' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.58 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.199 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1744 _exptl_absorpt_coefficient_mu 0.132 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.928 _exptl_absorpt_correction_T_max 0.962 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 32046 _diffrn_reflns_av_R_equivalents 0.0394 _diffrn_reflns_av_sigmaI/netI 0.0461 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 27.55 _reflns_number_total 10551 _reflns_number_gt 5988 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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 'calc w=1/[\s^2^(Fo^2^)+(0.0599P)^2^+0.5870P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 10551 _refine_ls_number_parameters 547 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0942 _refine_ls_R_factor_gt 0.0465 _refine_ls_wR_factor_ref 0.1421 _refine_ls_wR_factor_gt 0.1177 _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_restrained_S_all 1.014 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Si1 Si 0.35532(3) 0.16761(5) 0.32152(3) 0.05546(15) Uani 1 1 d . . . Si2 Si 0.15049(3) 0.55731(5) 0.17877(3) 0.06349(17) Uani 1 1 d . . . F1 F 0.77399(7) 0.28572(18) 0.42154(9) 0.1262(6) Uani 1 1 d . . . F2 F 0.41282(9) 0.85167(14) 0.43981(8) 0.1119(5) Uani 1 1 d . . . F3 F -0.25883(7) 0.46049(16) 0.10294(8) 0.1129(5) Uani 1 1 d . . . F4 F 0.07818(9) -0.13202(14) 0.05701(8) 0.1165(5) Uani 1 1 d . . . N1 N 0.36704(7) 0.28619(14) 0.20731(7) 0.0524(4) Uani 1 1 d . . . N2 N 0.31704(9) 0.20513(17) 0.17353(8) 0.0714(5) Uani 1 1 d . . . N3 N 0.29504(9) 0.23267(19) 0.11170(8) 0.0802(6) Uani 1 1 d . . . N4 N 0.14517(7) 0.44389(15) 0.29686(7) 0.0563(4) Uani 1 1 d . . . N5 N 0.19439(9) 0.52825(18) 0.32800(9) 0.0748(5) Uani 1 1 d . . . N6 N 0.21618(10) 0.5081(2) 0.39082(9) 0.0843(6) Uani 1 1 d . . . C1 C 0.49211(9) 0.42307(17) 0.35054(9) 0.0546(5) Uani 1 1 d . . . C2 C 0.44422(9) 0.35182(18) 0.31078(9) 0.0562(5) Uani 1 1 d . . . C3 C 0.39482(9) 0.27767(17) 0.27720(8) 0.0514(4) Uani 1 1 d . . . C4 C 0.56808(9) 0.38953(17) 0.36962(9) 0.0542(4) Uani 1 1 d . . . C5 C 0.59313(10) 0.34003(19) 0.32384(10) 0.0660(5) Uani 1 1 d . . . H5 H 0.5629 0.3301 0.2808 0.079 Uiso 1 1 calc R . . C6 C 0.66260(12) 0.3049(2) 0.34100(13) 0.0813(7) Uani 1 1 d . . . H6 H 0.6794 0.2719 0.3101 0.098 Uiso 1 1 calc R . . C7 C 0.70556(11) 0.3202(2) 0.40438(14) 0.0815(7) Uani 1 1 d . . . C8 C 0.68345(12) 0.3680(2) 0.45103(12) 0.0846(7) Uani 1 1 d . . . H8 H 0.7143 0.3772 0.4939 0.102 Uiso 1 1 calc R . . C9 C 0.61392(11) 0.4029(2) 0.43356(10) 0.0713(6) Uani 1 1 d . . . H9 H 0.5979 0.4355 0.4650 0.086 Uiso 1 1 calc R . . C10 C 0.47152(9) 0.53704(18) 0.37437(9) 0.0556(5) Uani 1 1 d . . . C11 C 0.51653(11) 0.63515(19) 0.39136(11) 0.0688(6) Uani 1 1 d . . . H11 H 0.5608 0.6292 0.3882 0.083 Uiso 1 1 calc R . . C12 C 0.49683(13) 0.7414(2) 0.41293(12) 0.0805(6) Uani 1 1 d . . . H12 H 0.5272 0.8067 0.4242 0.097 Uiso 1 1 calc R . . C13 C 0.43152(14) 0.7479(2) 0.41719(12) 0.0787(6) Uani 1 1 d . . . C14 C 0.38462(12) 0.6549(2) 0.39986(12) 0.0825(7) Uani 1 1 d . . . H14 H 0.3400 0.6626 0.4022 0.099 Uiso 1 1 calc R . . C15 C 0.40523(10) 0.5502(2) 0.37904(11) 0.0721(6) Uani 1 1 d . . . H15 H 0.3741 0.4859 0.3677 0.087 Uiso 1 1 calc R . . C16 C 0.37680(9) 0.36952(17) 0.16489(9) 0.0513(4) Uani 1 1 d . . . C17 C 0.33050(10) 0.3338(2) 0.10399(9) 0.0623(5) Uani 1 1 d . . . C18 C 0.32377(11) 0.4008(2) 0.04769(10) 0.0756(6) Uani 1 1 d . . . H18 H 0.2927 0.3779 0.0067 0.091 Uiso 1 1 calc R . . C19 C 0.36431(12) 0.5001(2) 0.05510(11) 0.0760(6) Uani 1 1 d . . . H19 H 0.3610 0.5462 0.0185 0.091 Uiso 1 1 calc R . . C20 C 0.41099(11) 0.5348(2) 0.11662(11) 0.0711(6) Uani 1 1 d . . . H20 H 0.4381 0.6033 0.1196 0.085 Uiso 1 1 calc R . . C21 C 0.41839(10) 0.47169(18) 0.17299(10) 0.0611(5) Uani 1 1 d . . . H21 H 0.4492 0.4957 0.2138 0.073 Uiso 1 1 calc R . . C22 C 0.40666(14) 0.1857(3) 0.41004(11) 0.0962(8) Uani 1 1 d . . . H22A H 0.3990 0.2645 0.4240 0.144 Uiso 1 1 calc R . . H22B H 0.4556 0.1753 0.4173 0.144 Uiso 1 1 calc R . . H22C H 0.3920 0.1266 0.4346 0.144 Uiso 1 1 calc R . . C23 C 0.26300(11) 0.2126(2) 0.30302(14) 0.0950(8) Uani 1 1 d . . . H23A H 0.2360 0.1917 0.2586 0.143 Uiso 1 1 calc R . . H23B H 0.2606 0.2978 0.3087 0.143 Uiso 1 1 calc R . . H23C H 0.2444 0.1719 0.3322 0.143 Uiso 1 1 calc R . . C24 C 0.36366(14) 0.0120(2) 0.29611(13) 0.0909(7) Uani 1 1 d . . . H24A H 0.3461 -0.0424 0.3209 0.136 Uiso 1 1 calc R . . H24B H 0.4121 -0.0054 0.3040 0.136 Uiso 1 1 calc R . . H24C H 0.3371 0.0029 0.2502 0.136 Uiso 1 1 calc R . . C25 C 0.01710(9) 0.30014(18) 0.15794(9) 0.0562(5) Uani 1 1 d . . . C26 C 0.06732(9) 0.36936(19) 0.19555(9) 0.0595(5) Uani 1 1 d . . . C27 C 0.11621(9) 0.44650(18) 0.22670(9) 0.0559(5) Uani 1 1 d . . . C28 C -0.05747(9) 0.33984(18) 0.14298(9) 0.0560(5) Uani 1 1 d . . . C29 C -0.07659(10) 0.3960(2) 0.19093(10) 0.0658(5) Uani 1 1 d . . . H29 H -0.0434 0.4064 0.2326 0.079 Uiso 1 1 calc R . . C30 C -0.14454(11) 0.4370(2) 0.17776(11) 0.0734(6) Uani 1 1 d . . . H30 H -0.1574 0.4745 0.2100 0.088 Uiso 1 1 calc R . . C31 C -0.19202(11) 0.4206(2) 0.11602(12) 0.0766(6) Uani 1 1 d . . . C32 C -0.17580(11) 0.3667(2) 0.06750(12) 0.0828(7) Uani 1 1 d . . . H32 H -0.2095 0.3576 0.0259 0.099 Uiso 1 1 calc R . . C33 C -0.10776(10) 0.3251(2) 0.08103(10) 0.0719(6) Uani 1 1 d . . . H33 H -0.0959 0.2872 0.0483 0.086 Uiso 1 1 calc R . . C34 C 0.03321(9) 0.18496(19) 0.13165(9) 0.0594(5) Uani 1 1 d . . . C35 C -0.01306(11) 0.0892(2) 0.11714(11) 0.0742(6) Uani 1 1 d . . . H35 H -0.0554 0.0970 0.1241 0.089 Uiso 1 1 calc R . . C36 C 0.00194(13) -0.0182(2) 0.09258(13) 0.0869(7) Uani 1 1 d . . . H36 H -0.0297 -0.0816 0.0830 0.104 Uiso 1 1 calc R . . C37 C 0.06411(14) -0.0281(2) 0.08296(12) 0.0832(7) Uani 1 1 d . . . C38 C 0.11270(14) 0.0628(3) 0.09778(13) 0.0909(8) Uani 1 1 d . . . H38 H 0.1554 0.0531 0.0917 0.109 Uiso 1 1 calc R . . C39 C 0.09677(11) 0.1682(2) 0.12179(12) 0.0780(6) Uani 1 1 d . . . H39 H 0.1293 0.2304 0.1318 0.094 Uiso 1 1 calc R . . C40 C 0.13599(9) 0.36562(18) 0.34157(9) 0.0549(5) Uani 1 1 d . . . C41 C 0.18181(10) 0.4083(2) 0.40176(10) 0.0675(6) Uani 1 1 d . . . C42 C 0.18854(13) 0.3490(3) 0.46011(11) 0.0866(7) Uani 1 1 d . . . H42 H 0.2188 0.3771 0.5003 0.104 Uiso 1 1 calc R . . C43 C 0.14961(14) 0.2493(3) 0.45608(12) 0.0889(8) Uani 1 1 d . . . H43 H 0.1534 0.2079 0.4943 0.107 Uiso 1 1 calc R . . C44 C 0.10337(12) 0.2065(2) 0.39567(12) 0.0802(7) Uani 1 1 d . . . H44 H 0.0772 0.1378 0.3951 0.096 Uiso 1 1 calc R . . C45 C 0.09572(10) 0.2629(2) 0.33741(11) 0.0655(5) Uani 1 1 d . . . H45 H 0.0653 0.2341 0.2975 0.079 Uiso 1 1 calc R . . C46 C 0.09675(17) 0.5334(3) 0.09142(13) 0.1158(10) Uani 1 1 d . . . H46A H 0.0480 0.5427 0.0855 0.174 Uiso 1 1 calc R . . H46B H 0.1047 0.4538 0.0786 0.174 Uiso 1 1 calc R . . H46C H 0.1097 0.5911 0.0649 0.174 Uiso 1 1 calc R . . C47 C 0.24306(13) 0.5190(3) 0.19412(16) 0.1132(10) Uani 1 1 d . . . H47A H 0.2472 0.4341 0.1890 0.170 Uiso 1 1 calc R . . H47B H 0.2712 0.5421 0.2379 0.170 Uiso 1 1 calc R . . H47C H 0.2589 0.5609 0.1634 0.170 Uiso 1 1 calc R . . C48 C 0.13940(17) 0.7128(2) 0.20209(15) 0.1101(9) Uani 1 1 d . . . H48A H 0.1532 0.7673 0.1747 0.165 Uiso 1 1 calc R . . H48B H 0.1681 0.7257 0.2471 0.165 Uiso 1 1 calc R . . H48C H 0.0911 0.7263 0.1966 0.165 Uiso 1 1 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 0.0581(3) 0.0566(3) 0.0558(3) 0.0015(3) 0.0250(3) 0.0014(2) Si2 0.0686(3) 0.0607(4) 0.0679(4) 0.0044(3) 0.0324(3) 0.0057(3) F1 0.0641(8) 0.1676(17) 0.1430(14) 0.0367(12) 0.0313(9) 0.0299(9) F2 0.1414(13) 0.0871(11) 0.1183(12) -0.0146(9) 0.0593(11) 0.0248(9) F3 0.0655(8) 0.1495(14) 0.1133(12) -0.0027(10) 0.0183(8) 0.0303(8) F4 0.1498(14) 0.0850(11) 0.1207(13) -0.0019(9) 0.0547(11) 0.0319(10) N1 0.0498(8) 0.0605(10) 0.0454(8) -0.0043(7) 0.0148(7) -0.0109(7) N2 0.0740(11) 0.0802(12) 0.0513(10) -0.0059(9) 0.0108(8) -0.0281(9) N3 0.0812(12) 0.0977(15) 0.0496(10) -0.0024(10) 0.0080(9) -0.0299(11) N4 0.0494(8) 0.0671(10) 0.0497(9) -0.0036(8) 0.0139(7) -0.0048(7) N5 0.0665(10) 0.0866(13) 0.0612(11) -0.0083(10) 0.0097(9) -0.0179(10) N6 0.0768(12) 0.1015(16) 0.0591(12) -0.0077(11) 0.0043(10) -0.0140(11) C1 0.0520(9) 0.0641(12) 0.0450(10) -0.0009(9) 0.0134(8) -0.0090(9) C2 0.0550(10) 0.0657(13) 0.0483(10) -0.0011(9) 0.0186(9) -0.0038(9) C3 0.0487(9) 0.0589(11) 0.0457(10) -0.0045(9) 0.0154(8) -0.0030(9) C4 0.0529(10) 0.0548(11) 0.0527(11) 0.0025(9) 0.0156(9) -0.0067(9) C5 0.0664(12) 0.0742(14) 0.0580(12) 0.0082(11) 0.0224(10) 0.0019(11) C6 0.0795(15) 0.0914(18) 0.0830(17) 0.0190(14) 0.0408(14) 0.0182(13) C7 0.0580(12) 0.0928(18) 0.0928(19) 0.0225(14) 0.0252(13) 0.0074(12) C8 0.0638(13) 0.0959(19) 0.0747(16) 0.0026(14) -0.0003(12) -0.0020(12) C9 0.0634(12) 0.0817(15) 0.0602(13) -0.0070(11) 0.0110(10) -0.0006(11) C10 0.0536(10) 0.0645(12) 0.0457(10) -0.0011(9) 0.0138(8) -0.0051(9) C11 0.0659(12) 0.0646(14) 0.0779(15) -0.0073(11) 0.0275(11) -0.0078(10) C12 0.0892(16) 0.0624(14) 0.0893(17) -0.0095(12) 0.0307(14) -0.0097(12) C13 0.1000(17) 0.0689(15) 0.0708(15) -0.0038(12) 0.0342(13) 0.0145(14) C14 0.0733(14) 0.0949(19) 0.0864(17) -0.0086(14) 0.0369(13) 0.0081(14) C15 0.0633(12) 0.0803(16) 0.0735(14) -0.0098(12) 0.0248(11) -0.0075(11) C16 0.0462(9) 0.0597(12) 0.0507(10) -0.0006(9) 0.0204(8) 0.0015(8) C17 0.0572(10) 0.0779(14) 0.0494(11) 0.0004(10) 0.0158(9) -0.0028(10) C18 0.0704(13) 0.1019(19) 0.0507(12) 0.0093(12) 0.0163(10) 0.0010(13) C19 0.0785(14) 0.0889(17) 0.0665(15) 0.0215(13) 0.0329(12) 0.0122(13) C20 0.0738(13) 0.0645(14) 0.0836(16) 0.0089(12) 0.0383(13) 0.0005(11) C21 0.0610(11) 0.0630(13) 0.0617(12) -0.0007(10) 0.0245(10) -0.0034(10) C22 0.123(2) 0.110(2) 0.0590(14) 0.0089(14) 0.0356(14) -0.0105(17) C23 0.0710(14) 0.0919(18) 0.138(2) 0.0304(17) 0.0568(15) 0.0128(13) C24 0.122(2) 0.0651(15) 0.0960(18) 0.0003(13) 0.0507(16) 0.0108(14) C25 0.0537(10) 0.0683(13) 0.0443(10) 0.0029(9) 0.0145(8) -0.0065(9) C26 0.0543(10) 0.0750(14) 0.0486(11) 0.0023(10) 0.0174(9) -0.0016(10) C27 0.0486(9) 0.0684(13) 0.0500(11) -0.0033(9) 0.0164(8) -0.0004(9) C28 0.0541(10) 0.0607(12) 0.0506(11) 0.0028(9) 0.0149(9) -0.0053(9) C29 0.0653(12) 0.0775(14) 0.0513(11) 0.0033(11) 0.0161(10) 0.0005(11) C30 0.0748(13) 0.0824(16) 0.0664(14) 0.0042(12) 0.0289(12) 0.0140(12) C31 0.0592(12) 0.0839(17) 0.0825(16) 0.0045(13) 0.0197(12) 0.0077(11) C32 0.0618(12) 0.0995(19) 0.0685(15) -0.0100(13) -0.0006(11) 0.0036(12) C33 0.0643(12) 0.0865(16) 0.0563(12) -0.0117(11) 0.0102(10) -0.0003(11) C34 0.0559(10) 0.0685(13) 0.0502(11) 0.0060(9) 0.0143(9) -0.0007(9) C35 0.0675(12) 0.0709(15) 0.0869(16) 0.0010(12) 0.0305(12) -0.0047(11) C36 0.0901(16) 0.0670(15) 0.1012(19) -0.0021(14) 0.0306(15) -0.0054(13) C37 0.1012(18) 0.0689(16) 0.0797(16) 0.0074(13) 0.0320(14) 0.0199(14) C38 0.0871(16) 0.096(2) 0.102(2) 0.0049(16) 0.0488(15) 0.0155(15) C39 0.0657(12) 0.0862(17) 0.0850(16) -0.0038(13) 0.0300(12) -0.0040(12) C40 0.0472(9) 0.0674(13) 0.0501(11) 0.0025(9) 0.0170(8) 0.0104(9) C41 0.0594(11) 0.0871(16) 0.0489(12) 0.0007(11) 0.0102(10) 0.0100(11) C42 0.0854(16) 0.113(2) 0.0537(13) 0.0078(14) 0.0148(12) 0.0167(15) C43 0.0975(18) 0.108(2) 0.0646(16) 0.0271(15) 0.0326(14) 0.0288(16) C44 0.0845(15) 0.0793(16) 0.0840(17) 0.0189(14) 0.0384(14) 0.0137(13) C45 0.0625(11) 0.0717(14) 0.0640(13) 0.0050(11) 0.0243(10) 0.0058(10) C46 0.156(3) 0.123(2) 0.0716(17) 0.0121(17) 0.0445(18) -0.013(2) C47 0.0879(16) 0.105(2) 0.174(3) 0.040(2) 0.0796(19) 0.0180(15) C48 0.160(3) 0.0707(17) 0.111(2) 0.0074(16) 0.061(2) 0.0238(18) _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_2 _geom_bond_publ_flag Si1 C24 1.845(2) . ? Si1 C23 1.848(2) . ? Si1 C22 1.854(2) . ? Si1 C3 1.9041(19) . ? Si2 C48 1.841(3) . ? Si2 C47 1.845(2) . ? Si2 C46 1.851(3) . ? Si2 C27 1.900(2) . ? F1 C7 1.365(2) . ? F2 C13 1.362(3) . ? F3 C31 1.363(2) . ? F4 C37 1.362(3) . ? N1 N2 1.367(2) . ? N1 C16 1.372(2) . ? N1 C3 1.429(2) . ? N2 N3 1.298(2) . ? N3 C17 1.380(3) . ? N4 C40 1.368(2) . ? N4 N5 1.368(2) . ? N4 C27 1.432(2) . ? N5 N6 1.301(2) . ? N6 C41 1.378(3) . ? C1 C2 1.319(2) . ? C1 C10 1.486(3) . ? C1 C4 1.501(2) . ? C2 C3 1.309(2) . ? C4 C5 1.383(3) . ? C4 C9 1.386(3) . ? C5 C6 1.386(3) . ? C6 C7 1.361(3) . ? C7 C8 1.356(3) . ? C8 C9 1.386(3) . ? C10 C11 1.391(3) . ? C10 C15 1.396(3) . ? C11 C12 1.384(3) . ? C12 C13 1.366(3) . ? C13 C14 1.370(3) . ? C14 C15 1.369(3) . ? C16 C17 1.389(3) . ? C16 C21 1.392(3) . ? C17 C18 1.400(3) . ? C18 C19 1.356(3) . ? C19 C20 1.398(3) . ? C20 C21 1.377(3) . ? C25 C26 1.313(3) . ? C25 C34 1.488(3) . ? C25 C28 1.503(2) . ? C26 C27 1.310(3) . ? C28 C29 1.385(3) . ? C28 C33 1.388(3) . ? C29 C30 1.388(3) . ? C30 C31 1.365(3) . ? C31 C32 1.353(3) . ? C32 C33 1.391(3) . ? C34 C35 1.385(3) . ? C34 C39 1.396(3) . ? C35 C36 1.387(3) . ? C36 C37 1.358(3) . ? C37 C38 1.373(3) . ? C38 C39 1.369(3) . ? C40 C45 1.392(3) . ? C40 C41 1.399(3) . ? C41 C42 1.396(3) . ? C42 C43 1.349(4) . ? C43 C44 1.406(3) . ? C44 C45 1.375(3) . ? 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_3 _geom_angle_publ_flag C24 Si1 C23 112.52(13) . . ? C24 Si1 C22 109.64(13) . . ? C23 Si1 C22 110.92(13) . . ? C24 Si1 C3 110.69(10) . . ? C23 Si1 C3 107.01(10) . . ? C22 Si1 C3 105.83(10) . . ? C48 Si2 C47 112.56(15) . . ? C48 Si2 C46 109.49(14) . . ? C47 Si2 C46 110.56(15) . . ? C48 Si2 C27 110.83(11) . . ? C47 Si2 C27 107.37(10) . . ? C46 Si2 C27 105.80(11) . . ? N2 N1 C16 109.93(14) . . ? N2 N1 C3 118.14(15) . . ? C16 N1 C3 131.70(15) . . ? N3 N2 N1 108.86(16) . . ? N2 N3 C17 108.31(16) . . ? C40 N4 N5 110.13(15) . . ? C40 N4 C27 131.65(16) . . ? N5 N4 C27 118.09(16) . . ? N6 N5 N4 108.85(17) . . ? N5 N6 C41 108.32(17) . . ? C2 C1 C10 120.63(16) . . ? C2 C1 C4 119.00(18) . . ? C10 C1 C4 120.34(15) . . ? C3 C2 C1 173.41(19) . . ? C2 C3 N1 119.55(16) . . ? C2 C3 Si1 120.09(14) . . ? N1 C3 Si1 120.18(12) . . ? C5 C4 C9 118.58(18) . . ? C5 C4 C1 120.25(17) . . ? C9 C4 C1 121.12(18) . . ? C4 C5 C6 121.1(2) . . ? C7 C6 C5 118.0(2) . . ? C8 C7 C6 123.0(2) . . ? C8 C7 F1 118.7(2) . . ? C6 C7 F1 118.3(2) . . ? C7 C8 C9 118.7(2) . . ? C4 C9 C8 120.6(2) . . ? C11 C10 C15 117.52(19) . . ? C11 C10 C1 121.61(16) . . ? C15 C10 C1 120.85(17) . . ? C12 C11 C10 121.4(2) . . ? C13 C12 C11 118.2(2) . . ? F2 C13 C12 118.1(2) . . ? F2 C13 C14 119.1(2) . . ? C12 C13 C14 122.8(2) . . ? C15 C14 C13 118.1(2) . . ? C14 C15 C10 122.0(2) . . ? N1 C16 C17 103.85(16) . . ? N1 C16 C21 133.84(17) . . ? C17 C16 C21 122.27(18) . . ? N3 C17 C16 109.05(17) . . ? N3 C17 C18 130.29(19) . . ? C16 C17 C18 120.6(2) . . ? C19 C18 C17 117.5(2) . . ? C18 C19 C20 121.4(2) . . ? C21 C20 C19 122.6(2) . . ? C20 C21 C16 115.66(19) . . ? C26 C25 C34 121.22(17) . . ? C26 C25 C28 117.96(19) . . ? C34 C25 C28 120.82(16) . . ? C27 C26 C25 173.0(2) . . ? C26 C27 N4 119.53(17) . . ? C26 C27 Si2 120.03(15) . . ? N4 C27 Si2 120.41(13) . . ? C29 C28 C33 118.66(18) . . ? C29 C28 C25 119.91(17) . . ? C33 C28 C25 121.39(18) . . ? C28 C29 C30 121.05(19) . . ? C31 C30 C29 118.0(2) . . ? C32 C31 F3 118.7(2) . . ? C32 C31 C30 123.1(2) . . ? F3 C31 C30 118.2(2) . . ? C31 C32 C33 118.7(2) . . ? C28 C33 C32 120.5(2) . . ? C35 C34 C39 117.0(2) . . ? C35 C34 C25 121.90(18) . . ? C39 C34 C25 121.05(19) . . ? C34 C35 C36 121.9(2) . . ? C37 C36 C35 118.2(2) . . ? C36 C37 F4 118.5(3) . . ? C36 C37 C38 122.5(2) . . ? F4 C37 C38 119.0(2) . . ? C39 C38 C37 118.3(2) . . ? C38 C39 C34 122.0(2) . . ? N4 C40 C45 134.58(18) . . ? N4 C40 C41 103.76(18) . . ? C45 C40 C41 121.63(19) . . ? N6 C41 C42 130.2(2) . . ? N6 C41 C40 108.93(18) . . ? C42 C41 C40 120.8(2) . . ? C43 C42 C41 117.5(2) . . ? C42 C43 C44 121.7(2) . . ? C45 C44 C43 122.0(2) . . ? C44 C45 C40 116.2(2) . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 27.55 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.272 _refine_diff_density_min -0.164 _refine_diff_density_rms 0.036