# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2009 data_global _journal_name_full 'New J.Chem.' _journal_coden_Cambridge 0440 _publ_contact_author_name 'H Le Bozec' _publ_contact_author_email LEBOZEC@UNIV-RENNES1.FR _publ_section_title ; A "reverse interruptor": novel molecular design of a fluorescent photochromic DTE-based bipyridine ; loop_ _publ_author_name 'H Le Bozec' 'Vincent Aubert' 'Abdou Boucekkine' 'Veronique Guerchais' 'Fatima Ibersiene' ; E.Ishow ; 'R Metivier' 'Keitaro Nakatani' 'loic Toupet' 'J Williams' # Attachment 'B823113C_bpy1(0,0).cif' data_va147 _database_code_depnum_ccdc_archive 'CCDC 640444' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C64 H58 F12 N4 S4 Si2' _chemical_formula_weight 1295.56 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' S S 0.1246 0.1234 '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/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.4582(5) _cell_length_b 19.8097(9) _cell_length_c 14.9154(7) _cell_angle_alpha 90.00 _cell_angle_beta 100.277(4) _cell_angle_gamma 90.00 _cell_volume 3040.5(2) _cell_formula_units_Z 2 _cell_measurement_temperature 100(1) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.415 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1340 _exptl_absorpt_coefficient_mu 0.277 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD Saphire 3 Xcalibur' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean 19.64 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21731 _diffrn_reflns_av_R_equivalents 0.0405 _diffrn_reflns_av_sigmaI/netI 0.0579 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.61 _diffrn_reflns_theta_max 27.00 _reflns_number_total 6585 _reflns_number_gt 4381 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd.,Version 1.171.26' _computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd.,Version 1.171.26' _computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd.,Version 1.171.26' _computing_structure_solution 'SIR-97_(Altomare & al., 1998)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON_(Spek, 1998)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.1246P)^2^+2.9515P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6585 _refine_ls_number_parameters 389 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1082 _refine_ls_R_factor_gt 0.0765 _refine_ls_wR_factor_ref 0.2604 _refine_ls_wR_factor_gt 0.2513 _refine_ls_goodness_of_fit_ref 1.270 _refine_ls_restrained_S_all 1.270 _refine_ls_shift/su_max 0.003 _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 1.05479(14) 0.60750(7) 0.83961(10) 0.0289(3) Uani 1 1 d . . . S1 S 0.86382(11) 0.21932(6) 0.87603(8) 0.0226(3) Uani 1 1 d . . . S2 S 1.17932(13) 0.46419(7) 0.87266(10) 0.0357(4) Uani 1 1 d . . . F1 F 0.8068(4) 0.2562(2) 0.5344(2) 0.0642(12) Uani 1 1 d . . . F2 F 1.0004(4) 0.21708(18) 0.5498(2) 0.0559(10) Uani 1 1 d . . . F3 F 1.0885(5) 0.3095(2) 0.4723(3) 0.0854(16) Uani 1 1 d . . . F4 F 0.8914(6) 0.3351(2) 0.4191(3) 0.0927(18) Uani 1 1 d . . . F5 F 1.1046(4) 0.4242(2) 0.5391(3) 0.0636(11) Uani 1 1 d . . . F6 F 0.8974(4) 0.43571(18) 0.5297(2) 0.0514(9) Uani 1 1 d . . . N1 N 0.5791(4) 0.55398(19) 0.9297(3) 0.0219(8) Uani 1 1 d . . . N2 N 1.0096(5) -0.1174(2) 0.8939(4) 0.0433(12) Uani 1 1 d . . . C1 C 0.5436(4) 0.4961(2) 0.9662(3) 0.0203(9) Uani 1 1 d . . . C2 C 0.5879(4) 0.4334(2) 0.9447(3) 0.0219(9) Uani 1 1 d . . . H2 H 0.5588 0.3939 0.9711 0.026 Uiso 1 1 calc R . . C3 C 0.6756(4) 0.4279(2) 0.8839(3) 0.0222(9) Uani 1 1 d . . . C4 C 0.7125(4) 0.4874(2) 0.8476(3) 0.0238(10) Uani 1 1 d . . . H4 H 0.7721 0.4867 0.8064 0.029 Uiso 1 1 calc R . . C5 C 0.6623(5) 0.5479(2) 0.8714(3) 0.0258(10) Uani 1 1 d . . . H5 H 0.6886 0.5880 0.8448 0.031 Uiso 1 1 calc R . . C6 C 0.7276(4) 0.3604(2) 0.8660(3) 0.0218(9) Uani 1 1 d . . . H6 H 0.7006 0.3230 0.8978 0.026 Uiso 1 1 calc R . . C7 C 0.8095(4) 0.3485(2) 0.8086(3) 0.0209(9) Uani 1 1 d . . . H7 H 0.8291 0.3849 0.7719 0.025 Uiso 1 1 calc R . . C8 C 0.8707(4) 0.2841(2) 0.7981(3) 0.0194(9) Uani 1 1 d . . . C9 C 0.9375(4) 0.2626(2) 0.7310(3) 0.0215(9) Uani 1 1 d . . . C10 C 0.9770(4) 0.1941(2) 0.7418(3) 0.0235(10) Uani 1 1 d . . . H10 H 1.0228 0.1717 0.7008 0.028 Uiso 1 1 calc R . . C11 C 0.9434(4) 0.1629(2) 0.8166(3) 0.0226(10) Uani 1 1 d . . . C12 C 0.9656(4) 0.0923(2) 0.8433(3) 0.0242(10) Uani 1 1 d . . . C13 C 1.0677(5) 0.0559(3) 0.8177(4) 0.0318(11) Uani 1 1 d . . . H13 H 1.1288 0.0789 0.7887 0.038 Uiso 1 1 calc R . . C14 C 1.0821(5) -0.0125(3) 0.8332(4) 0.0345(12) Uani 1 1 d . . . H14 H 1.1521 -0.0358 0.8143 0.041 Uiso 1 1 calc R . . C15 C 0.9945(5) -0.0482(3) 0.8766(4) 0.0333(12) Uani 1 1 d . . . C16 C 0.8941(5) -0.0118(3) 0.9058(4) 0.0310(11) Uani 1 1 d . . . H16 H 0.8353 -0.0344 0.9373 0.037 Uiso 1 1 calc R . . C17 C 0.8804(5) 0.0569(3) 0.8888(3) 0.0275(10) Uani 1 1 d . . . H17 H 0.8115 0.0806 0.9086 0.033 Uiso 1 1 calc R . . C18 C 1.0917(6) -0.1554(3) 0.8447(6) 0.061(2) Uani 1 1 d . . . H18A H 1.0931 -0.2028 0.8638 0.091 Uiso 1 1 calc R . . H18B H 1.1800 -0.1370 0.8577 0.091 Uiso 1 1 calc R . . H18C H 1.0578 -0.1523 0.7792 0.091 Uiso 1 1 calc R . . C19 C 0.9060(6) -0.1540(3) 0.9240(4) 0.0422(14) Uani 1 1 d . . . H19A H 0.9306 -0.2016 0.9331 0.063 Uiso 1 1 calc R . . H19B H 0.8268 -0.1505 0.8778 0.063 Uiso 1 1 calc R . . H19C H 0.8899 -0.1348 0.9815 0.063 Uiso 1 1 calc R . . C20 C 0.9602(5) 0.3037(2) 0.6528(3) 0.0246(10) Uani 1 1 d . . . C21 C 0.9315(5) 0.2735(3) 0.5583(4) 0.0321(11) Uani 1 1 d . . . C22 C 0.9727(7) 0.3285(3) 0.4955(4) 0.0476(15) Uani 1 1 d . . . C23 C 0.9957(5) 0.3906(3) 0.5537(4) 0.0325(12) Uani 1 1 d . . . C24 C 1.0049(4) 0.3678(2) 0.6508(3) 0.0249(10) Uani 1 1 d . . . C25 C 1.0553(4) 0.4137(2) 0.7256(3) 0.0262(10) Uani 1 1 d . . . C26 C 1.1419(5) 0.3955(3) 0.8020(4) 0.0300(11) Uani 1 1 d . . . C27 C 1.0764(5) 0.5183(3) 0.8025(4) 0.0297(11) Uani 1 1 d . . . C28 C 1.0200(5) 0.4838(2) 0.7261(3) 0.0272(10) Uani 1 1 d . . . H28 H 0.9624 0.5044 0.6774 0.033 Uiso 1 1 calc R . . C29 C 1.2055(5) 0.3287(3) 0.8299(4) 0.0407(14) Uani 1 1 d . . . H29A H 1.1497 0.3024 0.8632 0.053 Uiso 1 1 calc R . . H29B H 1.2898 0.3364 0.8692 0.053 Uiso 1 1 calc R . . H29C H 1.2182 0.3037 0.7755 0.053 Uiso 1 1 calc R . . C30 C 1.2097(5) 0.6538(3) 0.8417(5) 0.0397(13) Uani 1 1 d . . . H30A H 1.2788 0.6324 0.8855 0.060 Uiso 1 1 calc R . . H30B H 1.1993 0.7008 0.8599 0.060 Uiso 1 1 calc R . . H30C H 1.2329 0.6529 0.7809 0.060 Uiso 1 1 calc R . . C31 C 0.9212(5) 0.6467(3) 0.7577(4) 0.0370(12) Uani 1 1 d . . . H31A H 0.8405 0.6215 0.7578 0.056 Uiso 1 1 calc R . . H31B H 0.9429 0.6457 0.6965 0.056 Uiso 1 1 calc R . . H31C H 0.9095 0.6936 0.7756 0.056 Uiso 1 1 calc R . . C32 C 1.0120(6) 0.6055(3) 0.9547(4) 0.0418(14) Uani 1 1 d . . . H32A H 1.0831 0.5848 0.9975 0.063 Uiso 1 1 calc R . . H32B H 0.9325 0.5790 0.9531 0.063 Uiso 1 1 calc R . . H32C H 0.9977 0.6517 0.9744 0.063 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 0.0282(7) 0.0267(7) 0.0321(8) -0.0010(6) 0.0060(6) -0.0023(6) S1 0.0265(6) 0.0190(6) 0.0243(6) 0.0009(4) 0.0099(4) 0.0038(4) S2 0.0340(7) 0.0291(7) 0.0399(8) 0.0045(6) -0.0046(5) -0.0053(5) F1 0.058(2) 0.095(3) 0.039(2) -0.026(2) 0.0070(17) -0.019(2) F2 0.098(3) 0.0377(19) 0.0374(18) -0.0053(15) 0.0256(19) 0.0277(19) F3 0.118(4) 0.066(3) 0.096(4) -0.002(3) 0.081(3) 0.012(3) F4 0.158(5) 0.065(3) 0.039(2) 0.011(2) -0.027(3) -0.026(3) F5 0.059(2) 0.084(3) 0.053(2) 0.024(2) 0.0228(19) -0.017(2) F6 0.070(2) 0.045(2) 0.0376(19) 0.0074(15) 0.0061(17) 0.0261(18) N1 0.0239(19) 0.0170(19) 0.027(2) 0.0025(15) 0.0098(16) 0.0021(15) N2 0.038(3) 0.021(2) 0.069(4) 0.005(2) 0.005(2) 0.0038(19) C1 0.021(2) 0.019(2) 0.022(2) -0.0004(17) 0.0060(17) 0.0013(17) C2 0.026(2) 0.017(2) 0.025(2) 0.0029(18) 0.0095(18) -0.0020(18) C3 0.022(2) 0.025(2) 0.021(2) -0.0013(18) 0.0077(18) 0.0070(18) C4 0.024(2) 0.024(2) 0.026(2) -0.0013(19) 0.0108(19) 0.0083(18) C5 0.031(2) 0.022(2) 0.026(2) 0.0068(19) 0.011(2) 0.0044(19) C6 0.025(2) 0.016(2) 0.026(2) 0.0020(18) 0.0096(18) 0.0024(18) C7 0.023(2) 0.017(2) 0.022(2) -0.0007(17) 0.0032(18) 0.0040(17) C8 0.022(2) 0.015(2) 0.022(2) 0.0005(17) 0.0055(17) 0.0007(17) C9 0.023(2) 0.019(2) 0.024(2) -0.0016(18) 0.0067(18) 0.0009(17) C10 0.022(2) 0.020(2) 0.030(2) -0.0016(19) 0.0076(19) 0.0012(18) C11 0.023(2) 0.020(2) 0.026(2) -0.0031(18) 0.0077(18) 0.0033(18) C12 0.025(2) 0.020(2) 0.027(2) 0.0026(18) 0.0036(19) 0.0008(18) C13 0.032(3) 0.023(3) 0.043(3) 0.005(2) 0.013(2) 0.002(2) C14 0.033(3) 0.023(3) 0.048(3) -0.001(2) 0.009(2) 0.009(2) C15 0.034(3) 0.021(2) 0.042(3) 0.001(2) -0.001(2) 0.002(2) C16 0.028(2) 0.029(3) 0.036(3) 0.007(2) 0.004(2) -0.001(2) C17 0.028(2) 0.028(3) 0.026(2) 0.004(2) 0.0027(19) 0.004(2) C18 0.047(4) 0.025(3) 0.110(6) 0.001(4) 0.014(4) 0.010(3) C19 0.048(3) 0.027(3) 0.047(3) 0.010(3) -0.005(3) -0.004(2) C20 0.031(2) 0.022(2) 0.023(2) -0.0024(19) 0.0111(19) 0.0036(19) C21 0.044(3) 0.024(3) 0.029(3) -0.003(2) 0.011(2) 0.008(2) C22 0.068(4) 0.052(4) 0.026(3) 0.002(3) 0.017(3) 0.010(3) C23 0.034(3) 0.032(3) 0.034(3) 0.010(2) 0.014(2) 0.002(2) C24 0.024(2) 0.023(2) 0.030(3) 0.0042(19) 0.0094(19) 0.0046(19) C25 0.025(2) 0.023(2) 0.032(3) 0.005(2) 0.009(2) -0.0024(19) C26 0.025(2) 0.026(3) 0.037(3) 0.007(2) 0.003(2) -0.001(2) C27 0.027(2) 0.026(3) 0.036(3) 0.005(2) 0.006(2) -0.004(2) C28 0.029(2) 0.023(2) 0.030(3) 0.005(2) 0.007(2) 0.0011(19) C29 0.034(3) 0.030(3) 0.054(4) 0.012(3) -0.004(2) 0.004(2) C30 0.032(3) 0.023(3) 0.063(4) -0.002(3) 0.006(3) -0.003(2) C31 0.036(3) 0.041(3) 0.036(3) 0.002(2) 0.009(2) 0.000(2) C32 0.036(3) 0.056(4) 0.032(3) -0.007(3) 0.005(2) -0.007(3) _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 C32 1.850(6) . ? Si1 C31 1.855(6) . ? Si1 C30 1.858(5) . ? Si1 C27 1.876(5) . ? S1 C11 1.729(5) . ? S1 C8 1.740(4) . ? S2 C26 1.723(5) . ? S2 C27 1.733(5) . ? F1 C21 1.334(7) . ? F2 C21 1.348(6) . ? F3 C22 1.371(8) . ? F4 C22 1.301(7) . ? F5 C23 1.370(6) . ? F6 C23 1.361(6) . ? N1 C5 1.340(6) . ? N1 C1 1.351(6) . ? N2 C15 1.400(7) . ? N2 C18 1.437(9) . ? N2 C19 1.440(8) . ? C1 C2 1.382(6) . ? C1 C1 1.483(9) 3_667 ? C2 C3 1.404(6) . ? C2 H2 0.9500 . ? C3 C4 1.381(7) . ? C3 C6 1.485(6) . ? C4 C5 1.381(6) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C6 C7 1.336(6) . ? C6 H6 0.9500 . ? C7 C8 1.448(6) . ? C7 H7 0.9500 . ? C8 C9 1.386(6) . ? C9 C10 1.419(6) . ? C9 C20 1.477(6) . ? C10 C11 1.374(7) . ? C10 H10 0.9500 . ? C11 C12 1.462(6) . ? C12 C13 1.398(7) . ? C12 C17 1.401(7) . ? C13 C14 1.378(7) . ? C13 H13 0.9500 . ? C14 C15 1.402(8) . ? C14 H14 0.9500 . ? C15 C16 1.406(7) . ? C16 C17 1.387(7) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 C24 1.354(7) . ? C20 C21 1.511(7) . ? C21 C22 1.547(8) . ? C22 C23 1.501(8) . ? C23 C24 1.504(7) . ? C24 C25 1.462(7) . ? C25 C26 1.370(7) . ? C25 C28 1.438(7) . ? C26 C29 1.507(7) . ? C27 C28 1.370(7) . ? C28 H28 0.9500 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? 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 C32 Si1 C31 110.0(3) . . ? C32 Si1 C30 110.5(3) . . ? C31 Si1 C30 110.9(3) . . ? C32 Si1 C27 108.4(3) . . ? C31 Si1 C27 108.4(2) . . ? C30 Si1 C27 108.7(2) . . ? C11 S1 C8 93.0(2) . . ? C26 S2 C27 94.0(2) . . ? C5 N1 C1 116.3(4) . . ? C15 N2 C18 118.5(5) . . ? C15 N2 C19 119.0(5) . . ? C18 N2 C19 116.5(5) . . ? N1 C1 C2 122.8(4) . . ? N1 C1 C1 115.6(5) . 3_667 ? C2 C1 C1 121.6(5) . 3_667 ? C1 C2 C3 120.3(4) . . ? C1 C2 H2 119.9 . . ? C3 C2 H2 119.9 . . ? C4 C3 C2 116.6(4) . . ? C4 C3 C6 124.1(4) . . ? C2 C3 C6 119.2(4) . . ? C5 C4 C3 119.6(4) . . ? C5 C4 H4 120.2 . . ? C3 C4 H4 120.2 . . ? N1 C5 C4 124.4(4) . . ? N1 C5 H5 117.8 . . ? C4 C5 H5 117.8 . . ? C7 C6 C3 124.9(4) . . ? C7 C6 H6 117.6 . . ? C3 C6 H6 117.5 . . ? C6 C7 C8 124.8(4) . . ? C6 C7 H7 117.6 . . ? C8 C7 H7 117.6 . . ? C9 C8 C7 129.6(4) . . ? C9 C8 S1 110.0(3) . . ? C7 C8 S1 120.4(3) . . ? C8 C9 C10 112.7(4) . . ? C8 C9 C20 125.1(4) . . ? C10 C9 C20 122.1(4) . . ? C11 C10 C9 114.2(4) . . ? C11 C10 H10 122.9 . . ? C9 C10 H10 122.9 . . ? C10 C11 C12 126.9(4) . . ? C10 C11 S1 110.0(3) . . ? C12 C11 S1 123.0(4) . . ? C13 C12 C17 117.2(4) . . ? C13 C12 C11 120.8(4) . . ? C17 C12 C11 121.9(4) . . ? C14 C13 C12 121.9(5) . . ? C14 C13 H13 119.1 . . ? C12 C13 H13 119.1 . . ? C13 C14 C15 120.8(5) . . ? C13 C14 H14 119.6 . . ? C15 C14 H14 119.6 . . ? N2 C15 C14 121.2(5) . . ? N2 C15 C16 120.7(5) . . ? C14 C15 C16 118.1(5) . . ? C17 C16 C15 120.3(5) . . ? C17 C16 H16 119.8 . . ? C15 C16 H16 119.8 . . ? C16 C17 C12 121.7(5) . . ? C16 C17 H17 119.1 . . ? C12 C17 H17 119.1 . . ? N2 C18 H18A 109.5 . . ? N2 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? N2 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N2 C19 H19A 109.5 . . ? N2 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? N2 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C24 C20 C9 129.7(4) . . ? C24 C20 C21 111.3(4) . . ? C9 C20 C21 119.0(4) . . ? F1 C21 F2 106.0(5) . . ? F1 C21 C20 111.9(4) . . ? F2 C21 C20 113.3(4) . . ? F1 C21 C22 112.6(5) . . ? F2 C21 C22 108.4(4) . . ? C20 C21 C22 104.8(4) . . ? F4 C22 F3 106.0(5) . . ? F4 C22 C23 115.9(5) . . ? F3 C22 C23 108.3(6) . . ? F4 C22 C21 113.1(6) . . ? F3 C22 C21 108.3(5) . . ? C23 C22 C21 105.1(4) . . ? F6 C23 F5 104.5(4) . . ? F6 C23 C24 111.5(4) . . ? F5 C23 C24 112.8(4) . . ? F6 C23 C22 110.5(5) . . ? F5 C23 C22 111.0(5) . . ? C24 C23 C22 106.6(4) . . ? C20 C24 C25 130.2(4) . . ? C20 C24 C23 109.9(4) . . ? C25 C24 C23 120.0(4) . . ? C26 C25 C28 112.4(5) . . ? C26 C25 C24 124.5(4) . . ? C28 C25 C24 123.1(4) . . ? C25 C26 C29 130.8(5) . . ? C25 C26 S2 110.2(4) . . ? C29 C26 S2 118.9(4) . . ? C28 C27 S2 108.8(4) . . ? C28 C27 Si1 131.3(4) . . ? S2 C27 Si1 120.0(3) . . ? C27 C28 C25 114.5(4) . . ? C27 C28 H28 122.8 . . ? C25 C28 H28 122.8 . . ? C26 C29 H29A 109.5 . . ? C26 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C26 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? Si1 C30 H30A 109.5 . . ? Si1 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? Si1 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? Si1 C31 H31A 109.5 . . ? Si1 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? Si1 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? Si1 C32 H32A 109.5 . . ? Si1 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? Si1 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? 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 C5 N1 C1 C2 -1.0(7) . . . . ? C5 N1 C1 C1 177.3(5) . . . 3_667 ? N1 C1 C2 C3 1.4(7) . . . . ? C1 C1 C2 C3 -176.8(5) 3_667 . . . ? C1 C2 C3 C4 -0.6(7) . . . . ? C1 C2 C3 C6 176.5(4) . . . . ? C2 C3 C4 C5 -0.4(7) . . . . ? C6 C3 C4 C5 -177.3(4) . . . . ? C1 N1 C5 C4 -0.1(7) . . . . ? C3 C4 C5 N1 0.8(7) . . . . ? C4 C3 C6 C7 -4.4(7) . . . . ? C2 C3 C6 C7 178.7(4) . . . . ? C3 C6 C7 C8 173.3(4) . . . . ? C6 C7 C8 C9 167.2(5) . . . . ? C6 C7 C8 S1 -11.6(6) . . . . ? C11 S1 C8 C9 -2.4(4) . . . . ? C11 S1 C8 C7 176.6(4) . . . . ? C7 C8 C9 C10 -176.6(4) . . . . ? S1 C8 C9 C10 2.3(5) . . . . ? C7 C8 C9 C20 -0.1(8) . . . . ? S1 C8 C9 C20 178.8(4) . . . . ? C8 C9 C10 C11 -0.9(6) . . . . ? C20 C9 C10 C11 -177.5(4) . . . . ? C9 C10 C11 C12 177.2(4) . . . . ? C9 C10 C11 S1 -1.0(5) . . . . ? C8 S1 C11 C10 1.9(4) . . . . ? C8 S1 C11 C12 -176.3(4) . . . . ? C10 C11 C12 C13 26.4(7) . . . . ? S1 C11 C12 C13 -155.7(4) . . . . ? C10 C11 C12 C17 -148.4(5) . . . . ? S1 C11 C12 C17 29.6(6) . . . . ? C17 C12 C13 C14 2.3(8) . . . . ? C11 C12 C13 C14 -172.7(5) . . . . ? C12 C13 C14 C15 -0.6(8) . . . . ? C18 N2 C15 C14 -17.6(8) . . . . ? C19 N2 C15 C14 -169.4(5) . . . . ? C18 N2 C15 C16 165.2(6) . . . . ? C19 N2 C15 C16 13.3(8) . . . . ? C13 C14 C15 N2 -179.0(5) . . . . ? C13 C14 C15 C16 -1.7(8) . . . . ? N2 C15 C16 C17 179.6(5) . . . . ? C14 C15 C16 C17 2.3(8) . . . . ? C15 C16 C17 C12 -0.6(8) . . . . ? C13 C12 C17 C16 -1.7(7) . . . . ? C11 C12 C17 C16 173.2(5) . . . . ? C8 C9 C20 C24 48.4(7) . . . . ? C10 C9 C20 C24 -135.4(5) . . . . ? C8 C9 C20 C21 -131.5(5) . . . . ? C10 C9 C20 C21 44.7(6) . . . . ? C24 C20 C21 F1 -119.4(5) . . . . ? C9 C20 C21 F1 60.5(6) . . . . ? C24 C20 C21 F2 120.9(5) . . . . ? C9 C20 C21 F2 -59.2(6) . . . . ? C24 C20 C21 C22 2.9(6) . . . . ? C9 C20 C21 C22 -177.2(4) . . . . ? F1 C21 C22 F4 -16.7(7) . . . . ? F2 C21 C22 F4 100.2(6) . . . . ? C20 C21 C22 F4 -138.6(5) . . . . ? F1 C21 C22 F3 -133.9(5) . . . . ? F2 C21 C22 F3 -17.0(7) . . . . ? C20 C21 C22 F3 104.3(5) . . . . ? F1 C21 C22 C23 110.6(5) . . . . ? F2 C21 C22 C23 -132.5(5) . . . . ? C20 C21 C22 C23 -11.2(6) . . . . ? F4 C22 C23 F6 19.5(7) . . . . ? F3 C22 C23 F6 138.3(5) . . . . ? C21 C22 C23 F6 -106.2(5) . . . . ? F4 C22 C23 F5 -95.9(7) . . . . ? F3 C22 C23 F5 22.9(6) . . . . ? C21 C22 C23 F5 138.4(5) . . . . ? F4 C22 C23 C24 140.8(6) . . . . ? F3 C22 C23 C24 -100.3(5) . . . . ? C21 C22 C23 C24 15.2(6) . . . . ? C9 C20 C24 C25 6.3(9) . . . . ? C21 C20 C24 C25 -173.8(5) . . . . ? C9 C20 C24 C23 -173.0(5) . . . . ? C21 C20 C24 C23 6.9(6) . . . . ? F6 C23 C24 C20 106.5(5) . . . . ? F5 C23 C24 C20 -136.3(5) . . . . ? C22 C23 C24 C20 -14.2(6) . . . . ? F6 C23 C24 C25 -72.9(6) . . . . ? F5 C23 C24 C25 44.3(6) . . . . ? C22 C23 C24 C25 166.4(5) . . . . ? C20 C24 C25 C26 44.5(8) . . . . ? C23 C24 C25 C26 -136.2(5) . . . . ? C20 C24 C25 C28 -136.4(5) . . . . ? C23 C24 C25 C28 42.9(7) . . . . ? C28 C25 C26 C29 -179.5(5) . . . . ? C24 C25 C26 C29 -0.3(9) . . . . ? C28 C25 C26 S2 -0.3(5) . . . . ? C24 C25 C26 S2 178.9(4) . . . . ? C27 S2 C26 C25 1.4(4) . . . . ? C27 S2 C26 C29 -179.3(4) . . . . ? C26 S2 C27 C28 -2.2(4) . . . . ? C26 S2 C27 Si1 176.1(3) . . . . ? C32 Si1 C27 C28 125.5(5) . . . . ? C31 Si1 C27 C28 6.2(6) . . . . ? C30 Si1 C27 C28 -114.4(5) . . . . ? C32 Si1 C27 S2 -52.3(4) . . . . ? C31 Si1 C27 S2 -171.6(3) . . . . ? C30 Si1 C27 S2 67.8(4) . . . . ? S2 C27 C28 C25 2.4(6) . . . . ? Si1 C27 C28 C25 -175.6(4) . . . . ? C26 C25 C28 C27 -1.4(6) . . . . ? C24 C25 C28 C27 179.3(4) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 1.470 _refine_diff_density_min -0.729 _refine_diff_density_rms 0.103