# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2007 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _publ_section_title ;Intermolecular radical addition reactions of alfa-iodo cycloalkenones and synthetic study of formal synthesis of enantiopure fawcettimine ; _publ_contact_author_name 'Prof. Chimin Chau' _publ_contact_author_email CMCHAU@CSMU.EDU.TW loop_ _publ_author_name 'Chimin Chau' 'Kuan-Miao Liu' 'Chin-Kang Sha' # Attachment 'compound19.cif' data_jn20m _database_code_depnum_ccdc_archive 'CCDC 663530' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H27 N O Si' _chemical_formula_weight 289.49 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 Monoclinic _symmetry_space_group_name_H-M P2(1)/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 11.6687(8) _cell_length_b 12.3423(9) _cell_length_c 12.2850(9) _cell_angle_alpha 90.00 _cell_angle_beta 95.921(2) _cell_angle_gamma 90.00 _cell_volume 1759.8(2) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 5012 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 25 _exptl_crystal_description Columnar _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.7 _exptl_crystal_size_mid 0.5 _exptl_crystal_size_min 0.4 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.093 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 632 _exptl_absorpt_coefficient_mu 0.131 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.88685 _exptl_absorpt_correction_T_max 0.98096 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10218 _diffrn_reflns_av_R_equivalents 0.0201 _diffrn_reflns_av_sigmaI/netI 0.0213 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.75 _diffrn_reflns_theta_max 28.26 _reflns_number_total 3920 _reflns_number_gt 3064 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0839P)^2^+0.1976P] 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 3920 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0577 _refine_ls_R_factor_gt 0.0463 _refine_ls_wR_factor_ref 0.1435 _refine_ls_wR_factor_gt 0.1348 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _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 0.11459(4) 0.21744(4) 0.28183(4) 0.05530(17) Uani 1 1 d . . . O1 O 0.43214(10) 0.36205(10) 0.58786(9) 0.0569(3) Uani 1 1 d . . . N1 N 0.24742(16) -0.06355(14) 0.41648(19) 0.0904(6) Uani 1 1 d . . . C1 C 0.44350(13) 0.14973(11) 0.44326(12) 0.0449(3) Uani 1 1 d . . . C2 C 0.33656(12) 0.12047(11) 0.36502(12) 0.0433(3) Uani 1 1 d . . . C3A C 0.34075(12) 0.31525(11) 0.37034(11) 0.0409(3) Uani 1 1 d . . . C3 C 0.25582(12) 0.21923(11) 0.37384(12) 0.0421(3) Uani 1 1 d . . . C4 C 0.36219(15) 0.36041(13) 0.25706(13) 0.0537(4) Uani 1 1 d . . . C5 C 0.49020(14) 0.38778(14) 0.26843(13) 0.0540(4) Uani 1 1 d . . . C5A C 0.54370(13) 0.29041(12) 0.33131(12) 0.0458(3) Uani 1 1 d . . . C6 C 0.67137(14) 0.29728(14) 0.37292(14) 0.0547(4) Uani 1 1 d . . . C7 C 0.69695(13) 0.37237(13) 0.47050(14) 0.0521(4) Uani 1 1 d . . . C8 C 0.62791(14) 0.33356(13) 0.56240(13) 0.0521(4) Uani 1 1 d . . . C9 C 0.50149(13) 0.32756(11) 0.52922(11) 0.0416(3) Uani 1 1 d . . . C9A C 0.46131(11) 0.27189(11) 0.42073(11) 0.0381(3) Uani 1 1 d . . . C10 C 0.28603(15) 0.01661(13) 0.39340(16) 0.0580(4) Uani 1 1 d . . . C11 C 0.13376(18) 0.1459(2) 0.15142(18) 0.0868(7) Uani 1 1 d . . . C12 C 0.0605(2) 0.35634(19) 0.2565(3) 0.1127(11) Uani 1 1 d . . . C13 C 0.00795(17) 0.14259(18) 0.3549(2) 0.0815(6) Uani 1 1 d . . . C14 C 0.82523(15) 0.37430(18) 0.51077(19) 0.0746(6) Uani 1 1 d . . . H1A H 0.3163 0.3755 0.4168 0.080 Uiso 1 1 d . . . H2A H 0.3423 0.3080 0.2011 0.080 Uiso 1 1 d . . . H2B H 0.3121 0.4210 0.2342 0.080 Uiso 1 1 d . . . H3A H 0.5208 0.3983 0.1995 0.080 Uiso 1 1 d . . . H3B H 0.5030 0.4559 0.3104 0.080 Uiso 1 1 d . . . H4A H 0.5304 0.2303 0.2824 0.080 Uiso 1 1 d . . . H5A H 0.7098 0.3178 0.3141 0.080 Uiso 1 1 d . . . H5B H 0.6970 0.2256 0.3978 0.080 Uiso 1 1 d . . . H6A H 0.6734 0.4455 0.4484 0.080 Uiso 1 1 d . . . H7A H 0.6391 0.3743 0.6204 0.080 Uiso 1 1 d . . . H7B H 0.6527 0.2611 0.5847 0.080 Uiso 1 1 d . . . H10A H 0.5161 0.1057 0.4339 0.080 Uiso 1 1 d . . . H10B H 0.4262 0.1403 0.5185 0.080 Uiso 1 1 d . . . H11A H 0.3584 0.1136 0.2961 0.080 Uiso 1 1 d . . . H12A H 0.2353 0.2150 0.4432 0.080 Uiso 1 1 d . . . H13A H 0.1044 0.3895 0.2109 0.080 Uiso 1 1 d . . . H13B H -0.0169 0.3556 0.2157 0.080 Uiso 1 1 d . . . H13C H 0.0674 0.3990 0.3163 0.080 Uiso 1 1 d . . . H14A H 0.0592 0.1433 0.1021 0.080 Uiso 1 1 d . . . H14B H 0.2043 0.1616 0.1218 0.080 Uiso 1 1 d . . . H14C H 0.1531 0.0765 0.1723 0.080 Uiso 1 1 d . . . H15A H -0.0606 0.1458 0.3190 0.080 Uiso 1 1 d . . . H15B H 0.0417 0.0669 0.3699 0.080 Uiso 1 1 d . . . H15C H -0.0050 0.1729 0.4224 0.080 Uiso 1 1 d . . . H16A H 0.8710 0.4001 0.4535 0.080 Uiso 1 1 d . . . H16B H 0.8539 0.3019 0.5402 0.080 Uiso 1 1 d . . . H16C H 0.8355 0.4213 0.5707 0.080 Uiso 1 1 d . . . 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 0.0381(2) 0.0547(3) 0.0715(3) -0.0043(2) -0.0019(2) 0.00240(17) O1 0.0543(7) 0.0729(8) 0.0439(6) -0.0130(5) 0.0069(5) 0.0051(5) N1 0.0789(12) 0.0481(9) 0.1435(19) 0.0170(10) 0.0078(11) -0.0063(8) C1 0.0468(8) 0.0402(7) 0.0465(8) 0.0017(6) -0.0005(6) 0.0040(6) C2 0.0444(8) 0.0376(7) 0.0478(8) -0.0037(6) 0.0035(6) 0.0014(6) C3A 0.0429(7) 0.0377(7) 0.0408(7) -0.0019(5) -0.0015(5) 0.0026(5) C3 0.0420(7) 0.0392(7) 0.0454(8) -0.0029(6) 0.0056(6) 0.0027(6) C4 0.0561(9) 0.0542(9) 0.0477(8) 0.0087(7) -0.0091(7) -0.0055(7) C5 0.0576(9) 0.0606(9) 0.0424(8) 0.0087(7) -0.0021(6) -0.0123(7) C5A 0.0483(8) 0.0508(8) 0.0385(7) -0.0052(6) 0.0053(6) -0.0020(6) C6 0.0463(9) 0.0661(10) 0.0529(9) -0.0015(7) 0.0112(7) 0.0012(7) C7 0.0413(8) 0.0515(9) 0.0620(10) 0.0007(7) -0.0029(7) -0.0006(6) C8 0.0482(9) 0.0613(9) 0.0449(8) -0.0085(7) -0.0046(6) 0.0020(7) C9 0.0480(8) 0.0404(7) 0.0359(7) -0.0010(6) 0.0021(6) 0.0009(6) C9A 0.0392(7) 0.0383(7) 0.0359(7) -0.0014(5) 0.0007(5) 0.0016(5) C10 0.0531(9) 0.0437(8) 0.0764(11) -0.0003(8) 0.0029(8) 0.0034(7) C11 0.0551(11) 0.133(2) 0.0694(13) -0.0177(12) -0.0089(9) -0.0089(11) C12 0.0625(14) 0.0721(14) 0.196(3) 0.0219(16) -0.0252(16) 0.0119(11) C13 0.0498(10) 0.0871(14) 0.1097(17) -0.0163(12) 0.0182(10) -0.0090(9) C14 0.0454(10) 0.0868(14) 0.0885(15) 0.0036(11) -0.0074(9) -0.0060(9) _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 C12 1.842(2) . ? Si1 C13 1.854(2) . ? Si1 C11 1.863(2) . ? Si1 C3 1.9000(15) . ? O1 C9 1.2146(18) . ? N1 C10 1.135(2) . ? C1 C2 1.537(2) . ? C1 C9A 1.5508(19) . ? C1 H10A 1.0229 . ? C1 H10B 0.9736 . ? C2 C10 1.468(2) . ? C2 C3 1.5513(19) . ? C2 H11A 0.9127 . ? C3A C4 1.543(2) . ? C3A C3 1.548(2) . ? C3A C9A 1.5713(19) . ? C3A H1A 0.9962 . ? C3 H12A 0.9104 . ? C4 C5 1.524(2) . ? C4 H2A 0.9550 . ? C4 H2B 0.9724 . ? C5 C5A 1.527(2) . ? C5 H3A 0.9617 . ? C5 H3B 0.9901 . ? C5A C6 1.527(2) . ? C5A C9A 1.549(2) . ? C5A H4A 0.9566 . ? C6 C7 1.520(2) . ? C6 H5A 0.9247 . ? C6 H5B 0.9732 . ? C7 C14 1.527(2) . ? C7 C8 1.530(2) . ? C7 H6A 0.9737 . ? C8 C9 1.491(2) . ? C8 H7A 0.8707 . ? C8 H7B 0.9703 . ? C9 C9A 1.5295(18) . ? C11 H14A 1.0075 . ? C11 H14B 0.9541 . ? C11 H14C 0.9157 . ? C12 H13A 0.8951 . ? C12 H13B 0.9868 . ? C12 H13C 0.9011 . ? C13 H15A 0.8741 . ? C13 H15B 1.0231 . ? C13 H15C 0.9356 . ? C14 H16A 0.9789 . ? C14 H16B 1.0083 . ? C14 H16C 0.9355 . ? 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 C12 Si1 C13 108.08(12) . . ? C12 Si1 C11 111.40(15) . . ? C13 Si1 C11 109.07(11) . . ? C12 Si1 C3 110.53(9) . . ? C13 Si1 C3 107.57(9) . . ? C11 Si1 C3 110.09(8) . . ? C2 C1 C9A 103.41(11) . . ? C2 C1 H10A 115.7 . . ? C9A C1 H10A 111.6 . . ? C2 C1 H10B 109.3 . . ? C9A C1 H10B 109.3 . . ? H10A C1 H10B 107.4 . . ? C10 C2 C1 112.13(13) . . ? C10 C2 C3 114.07(12) . . ? C1 C2 C3 103.38(11) . . ? C10 C2 H11A 107.2 . . ? C1 C2 H11A 108.4 . . ? C3 C2 H11A 111.6 . . ? C4 C3A C3 117.72(12) . . ? C4 C3A C9A 104.86(12) . . ? C3 C3A C9A 106.14(11) . . ? C4 C3A H1A 109.2 . . ? C3 C3A H1A 109.5 . . ? C9A C3A H1A 109.0 . . ? C3A C3 C2 101.80(11) . . ? C3A C3 Si1 120.72(10) . . ? C2 C3 Si1 116.43(9) . . ? C3A C3 H12A 107.5 . . ? C2 C3 H12A 104.0 . . ? Si1 C3 H12A 105.1 . . ? C5 C4 C3A 104.24(12) . . ? C5 C4 H2A 112.3 . . ? C3A C4 H2A 110.8 . . ? C5 C4 H2B 114.2 . . ? C3A C4 H2B 112.9 . . ? H2A C4 H2B 102.6 . . ? C4 C5 C5A 102.57(12) . . ? C4 C5 H3A 113.5 . . ? C5A C5 H3A 112.5 . . ? C4 C5 H3B 109.3 . . ? C5A C5 H3B 111.9 . . ? H3A C5 H3B 107.1 . . ? C6 C5A C5 117.36(13) . . ? C6 C5A C9A 115.22(12) . . ? C5 C5A C9A 102.92(12) . . ? C6 C5A H4A 110.0 . . ? C5 C5A H4A 105.2 . . ? C9A C5A H4A 105.0 . . ? C7 C6 C5A 113.78(13) . . ? C7 C6 H5A 112.2 . . ? C5A C6 H5A 106.8 . . ? C7 C6 H5B 106.1 . . ? C5A C6 H5B 108.2 . . ? H5A C6 H5B 109.7 . . ? C6 C7 C14 111.78(15) . . ? C6 C7 C8 108.39(13) . . ? C14 C7 C8 109.81(14) . . ? C6 C7 H6A 108.6 . . ? C14 C7 H6A 108.4 . . ? C8 C7 H6A 109.9 . . ? C9 C8 C7 113.28(12) . . ? C9 C8 H7A 108.3 . . ? C7 C8 H7A 112.1 . . ? C9 C8 H7B 106.8 . . ? C7 C8 H7B 109.4 . . ? H7A C8 H7B 106.6 . . ? O1 C9 C8 121.42(13) . . ? O1 C9 C9A 120.74(13) . . ? C8 C9 C9A 117.78(12) . . ? C9 C9A C5A 113.25(11) . . ? C9 C9A C1 108.41(11) . . ? C5A C9A C1 111.98(11) . . ? C9 C9A C3A 111.83(11) . . ? C5A C9A C3A 105.44(11) . . ? C1 C9A C3A 105.69(11) . . ? N1 C10 C2 179.3(2) . . ? Si1 C11 H14A 111.1 . . ? Si1 C11 H14B 114.6 . . ? H14A C11 H14B 120.2 . . ? Si1 C11 H14C 104.5 . . ? H14A C11 H14C 108.1 . . ? H14B C11 H14C 95.7 . . ? Si1 C12 H13A 108.9 . . ? Si1 C12 H13B 110.9 . . ? H13A C12 H13B 103.8 . . ? Si1 C12 H13C 114.0 . . ? H13A C12 H13C 103.5 . . ? H13B C12 H13C 114.8 . . ? Si1 C13 H15A 111.0 . . ? Si1 C13 H15B 106.1 . . ? H15A C13 H15B 116.6 . . ? Si1 C13 H15C 114.1 . . ? H15A C13 H15C 101.9 . . ? H15B C13 H15C 107.4 . . ? C7 C14 H16A 111.2 . . ? C7 C14 H16B 112.3 . . ? H16A C14 H16B 111.1 . . ? C7 C14 H16C 107.8 . . ? H16A C14 H16C 109.3 . . ? H16B C14 H16C 104.9 . . ? _diffrn_measured_fraction_theta_max 0.898 _diffrn_reflns_theta_full 28.26 _diffrn_measured_fraction_theta_full 0.898 _refine_diff_density_max 0.278 _refine_diff_density_min -0.181 _refine_diff_density_rms 0.040 # Attachment 'compound 18.cif' data_mr19m _database_code_depnum_ccdc_archive 'CCDC 663531' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H27 N O Si' _chemical_formula_weight 289.49 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 Monoclinic _symmetry_space_group_name_H-M P2(1)/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 7.5791(14) _cell_length_b 12.075(2) _cell_length_c 19.243(4) _cell_angle_alpha 90.00 _cell_angle_beta 91.904(3) _cell_angle_gamma 90.00 _cell_volume 1760.1(6) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 965 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 25 _exptl_crystal_description Columnar _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.65 _exptl_crystal_size_mid 0.55 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.092 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 632 _exptl_absorpt_coefficient_mu 0.131 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8862 _exptl_absorpt_correction_T_max 0.9700 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10942 _diffrn_reflns_av_R_equivalents 0.0240 _diffrn_reflns_av_sigmaI/netI 0.0256 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 28.31 _reflns_number_total 4155 _reflns_number_gt 2777 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0779P)^2^+0.1447P] 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 4155 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0780 _refine_ls_R_factor_gt 0.0499 _refine_ls_wR_factor_ref 0.1503 _refine_ls_wR_factor_gt 0.1341 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _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 0.09504(7) 0.68350(5) 0.39487(3) 0.0632(2) Uani 1 1 d . . . O1 O 0.2617(2) 1.07320(13) 0.50648(6) 0.0754(4) Uani 1 1 d . . . N1 N 0.0252(3) 0.85421(17) 0.22060(10) 0.0860(5) Uani 1 1 d . . . C1 C 0.0356(2) 1.02773(15) 0.36743(10) 0.0580(4) Uani 1 1 d . . . H1A H -0.0299 1.0548 0.4064 0.070 Uiso 1 1 calc R . . H1B H 0.0108 1.0752 0.3276 0.070 Uiso 1 1 calc R . . C2 C -0.0146(2) 0.90725(15) 0.35061(9) 0.0568(4) Uani 1 1 d . . . H2A H -0.1385 0.8955 0.3616 0.068 Uiso 1 1 calc R . . C3A C 0.2802(2) 0.90292(14) 0.40545(8) 0.0513(4) Uani 1 1 d . . . H3AA H 0.3297 0.9002 0.4531 0.062 Uiso 1 1 calc R . . C3 C 0.1033(2) 0.83960(15) 0.40185(8) 0.0536(4) Uani 1 1 d . . . H3A H 0.0526 0.8546 0.4471 0.064 Uiso 1 1 calc R . . C4 C 0.4240(2) 0.86883(15) 0.35437(10) 0.0599(5) Uani 1 1 d . . . H4A H 0.5087 0.8188 0.3765 0.072 Uiso 1 1 calc R . . H4B H 0.3717 0.8329 0.3136 0.072 Uiso 1 1 calc R . . C5A C 0.3521(2) 1.05295(15) 0.32320(8) 0.0507(4) Uani 1 1 d . . . H5AA H 0.2880 1.0265 0.2813 0.061 Uiso 1 1 calc R . . C5 C 0.5109(2) 0.97657(15) 0.33510(9) 0.0579(4) Uani 1 1 d . . . H5A H 0.5777 0.9688 0.2932 0.069 Uiso 1 1 calc R . . H5B H 0.5885 1.0034 0.3725 0.069 Uiso 1 1 calc R . . C6 C 0.3924(3) 1.17444(15) 0.31171(9) 0.0616(5) Uani 1 1 d . . . H6A H 0.2873 1.2103 0.2924 0.074 Uiso 1 1 calc R . . H6B H 0.4835 1.1803 0.2777 0.074 Uiso 1 1 calc R . . C7 C 0.4530(3) 1.23604(16) 0.37695(10) 0.0645(5) Uani 1 1 d . . . H7A H 0.5613 1.2010 0.3954 0.077 Uiso 1 1 calc R . . C8 C 0.3105(3) 1.22300(18) 0.43020(11) 0.0774(6) Uani 1 1 d . . . H8A H 0.3478 1.2609 0.4726 0.093 Uiso 1 1 calc R . . H8B H 0.2032 1.2584 0.4126 0.093 Uiso 1 1 calc R . . C9A C 0.23644(19) 1.02571(14) 0.38581(8) 0.0476(4) Uani 1 1 d . . . C9 C 0.2711(2) 1.10463(16) 0.44688(9) 0.0568(4) Uani 1 1 d . . . C10 C 0.0100(2) 0.87837(16) 0.27729(11) 0.0622(5) Uani 1 1 d . . . C11 C 0.1929(4) 0.6275(2) 0.47753(14) 0.1161(10) Uani 1 1 d . . . H11A H 0.1912 0.5481 0.4760 0.174 Uiso 1 1 calc R . . H11B H 0.1254 0.6528 0.5158 0.174 Uiso 1 1 calc R . . H11C H 0.3125 0.6529 0.4834 0.174 Uiso 1 1 calc R . . C12 C 0.2159(3) 0.62324(17) 0.32090(13) 0.0858(7) Uani 1 1 d . . . H12A H 0.2045 0.5441 0.3215 0.129 Uiso 1 1 calc R . . H12B H 0.3384 0.6430 0.3253 0.129 Uiso 1 1 calc R . . H12C H 0.1669 0.6517 0.2779 0.129 Uiso 1 1 calc R . . C13 C -0.1407(3) 0.6421(2) 0.38383(13) 0.0881(7) Uani 1 1 d . . . H13D H -0.1487 0.5630 0.3801 0.132 Uiso 1 1 calc R . . H13A H -0.1907 0.6755 0.3424 0.132 Uiso 1 1 calc R . . H13B H -0.2044 0.6666 0.4233 0.132 Uiso 1 1 calc R . . C14 C 0.4928(4) 1.35777(18) 0.36184(13) 0.0917(7) Uani 1 1 d . . . H14A H 0.5825 1.3624 0.3279 0.138 Uiso 1 1 calc R . . H14B H 0.5332 1.3937 0.4039 0.138 Uiso 1 1 calc R . . H14C H 0.3874 1.3936 0.3442 0.138 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 0.0631(3) 0.0661(3) 0.0603(3) 0.0068(2) -0.0007(2) 0.0018(2) O1 0.0885(10) 0.0963(10) 0.0421(7) -0.0072(7) 0.0102(6) -0.0031(8) N1 0.0970(14) 0.0957(14) 0.0639(12) -0.0054(10) -0.0200(10) -0.0036(11) C1 0.0411(9) 0.0677(11) 0.0649(10) -0.0047(9) -0.0008(7) 0.0127(8) C2 0.0377(8) 0.0686(11) 0.0638(11) -0.0015(8) -0.0018(7) 0.0067(8) C3A 0.0440(9) 0.0643(10) 0.0452(8) -0.0007(7) -0.0027(7) 0.0100(7) C3 0.0457(9) 0.0698(11) 0.0457(9) 0.0004(8) 0.0042(7) 0.0064(8) C4 0.0429(9) 0.0672(11) 0.0697(11) -0.0049(9) 0.0039(8) 0.0154(8) C5A 0.0463(9) 0.0686(11) 0.0372(8) -0.0044(7) -0.0003(6) 0.0092(8) C5 0.0402(9) 0.0744(12) 0.0594(10) -0.0068(9) 0.0065(7) 0.0091(8) C6 0.0615(11) 0.0747(12) 0.0486(10) 0.0054(8) 0.0009(8) 0.0081(9) C7 0.0657(12) 0.0679(12) 0.0594(11) 0.0039(9) -0.0062(9) 0.0017(9) C8 0.0993(17) 0.0732(13) 0.0600(12) -0.0178(10) 0.0070(11) 0.0018(12) C9A 0.0381(8) 0.0631(10) 0.0415(8) -0.0035(7) -0.0008(6) 0.0105(7) C9 0.0486(9) 0.0770(12) 0.0451(9) -0.0078(8) 0.0052(7) 0.0061(8) C10 0.0533(10) 0.0669(12) 0.0651(12) 0.0030(9) -0.0190(8) 0.0021(8) C11 0.145(3) 0.106(2) 0.095(2) 0.0333(16) -0.0353(18) -0.0037(18) C12 0.0921(17) 0.0654(13) 0.1007(17) -0.0099(12) 0.0164(13) 0.0076(11) C13 0.0788(15) 0.0960(17) 0.0897(17) -0.0035(13) 0.0066(12) -0.0160(13) C14 0.1119(19) 0.0734(14) 0.0890(16) 0.0093(12) -0.0090(14) -0.0071(13) _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 C11 1.860(2) . ? Si1 C13 1.861(2) . ? Si1 C12 1.866(2) . ? Si1 C3 1.8905(19) . ? O1 C9 1.212(2) . ? N1 C10 1.139(2) . ? C1 C2 1.535(3) . ? C1 C9A 1.551(2) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C10 1.471(3) . ? C2 C3 1.542(2) . ? C2 H2A 0.9800 . ? C3A C3 1.543(2) . ? C3A C4 1.547(2) . ? C3A C9A 1.563(2) . ? C3A H3AA 0.9800 . ? C3 H3A 0.9800 . ? C4 C5 1.510(3) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5A C6 1.516(3) . ? C5A C5 1.528(2) . ? C5A C9A 1.549(2) . ? C5A H5AA 0.9800 . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.517(3) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.521(3) . ? C7 C14 1.530(3) . ? C7 H7A 0.9800 . ? C8 C9 1.497(3) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9A C9 1.529(2) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 H13D 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? 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 C11 Si1 C13 110.74(13) . . ? C11 Si1 C12 108.60(13) . . ? C13 Si1 C12 107.59(11) . . ? C11 Si1 C3 106.87(11) . . ? C13 Si1 C3 107.76(9) . . ? C12 Si1 C3 115.29(9) . . ? C2 C1 C9A 105.51(13) . . ? C2 C1 H1A 110.6 . . ? C9A C1 H1A 110.6 . . ? C2 C1 H1B 110.6 . . ? C9A C1 H1B 110.6 . . ? H1A C1 H1B 108.8 . . ? C10 C2 C1 112.86(15) . . ? C10 C2 C3 113.48(14) . . ? C1 C2 C3 103.46(14) . . ? C10 C2 H2A 108.9 . . ? C1 C2 H2A 108.9 . . ? C3 C2 H2A 108.9 . . ? C3 C3A C4 117.96(14) . . ? C3 C3A C9A 106.37(12) . . ? C4 C3A C9A 104.31(13) . . ? C3 C3A H3AA 109.3 . . ? C4 C3A H3AA 109.3 . . ? C9A C3A H3AA 109.3 . . ? C2 C3 C3A 104.50(14) . . ? C2 C3 Si1 117.74(12) . . ? C3A C3 Si1 121.58(11) . . ? C2 C3 H3A 103.6 . . ? C3A C3 H3A 103.6 . . ? Si1 C3 H3A 103.6 . . ? C5 C4 C3A 104.42(14) . . ? C5 C4 H4A 110.9 . . ? C3A C4 H4A 110.9 . . ? C5 C4 H4B 110.9 . . ? C3A C4 H4B 110.9 . . ? H4A C4 H4B 108.9 . . ? C6 C5A C5 116.37(15) . . ? C6 C5A C9A 116.16(13) . . ? C5 C5A C9A 102.64(13) . . ? C6 C5A H5AA 107.0 . . ? C5 C5A H5AA 107.0 . . ? C9A C5A H5AA 107.0 . . ? C4 C5 C5A 102.04(14) . . ? C4 C5 H5A 111.4 . . ? C5A C5 H5A 111.4 . . ? C4 C5 H5B 111.4 . . ? C5A C5 H5B 111.4 . . ? H5A C5 H5B 109.2 . . ? C5A C6 C7 114.25(14) . . ? C5A C6 H6A 108.7 . . ? C7 C6 H6A 108.7 . . ? C5A C6 H6B 108.7 . . ? C7 C6 H6B 108.7 . . ? H6A C6 H6B 107.6 . . ? C6 C7 C8 107.73(16) . . ? C6 C7 C14 111.71(17) . . ? C8 C7 C14 112.09(18) . . ? C6 C7 H7A 108.4 . . ? C8 C7 H7A 108.4 . . ? C14 C7 H7A 108.4 . . ? C9 C8 C7 113.21(16) . . ? C9 C8 H8A 108.9 . . ? C7 C8 H8A 108.9 . . ? C9 C8 H8B 108.9 . . ? C7 C8 H8B 108.9 . . ? H8A C8 H8B 107.7 . . ? C9 C9A C5A 112.23(14) . . ? C9 C9A C1 107.93(12) . . ? C5A C9A C1 113.30(13) . . ? C9 C9A C3A 112.07(13) . . ? C5A C9A C3A 105.57(12) . . ? C1 C9A C3A 105.60(13) . . ? O1 C9 C8 121.34(16) . . ? O1 C9 C9A 121.19(17) . . ? C8 C9 C9A 117.43(15) . . ? N1 C10 C2 178.2(2) . . ? Si1 C11 H11A 109.5 . . ? Si1 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? Si1 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? Si1 C12 H12A 109.5 . . ? Si1 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? Si1 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? Si1 C13 H13D 109.5 . . ? Si1 C13 H13A 109.5 . . ? H13D C13 H13A 109.5 . . ? Si1 C13 H13B 109.5 . . ? H13D C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C7 C14 H14A 109.5 . . ? C7 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C7 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.951 _diffrn_reflns_theta_full 28.31 _diffrn_measured_fraction_theta_full 0.951 _refine_diff_density_max 0.308 _refine_diff_density_min -0.166 _refine_diff_density_rms 0.036