# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'N Simpkins' _publ_contact_author_email N.SIMPKINS@BHAM.AC.UK _publ_section_title ; Bridgehead Enolates and Bridgehead Alkenes in a Welwistatin Model Series ; loop_ _publ_author_name 'N Simpkins' 'Gurdip Bhalay' 'Alexander Blake' 'Valerie Boissel' 'William Lewis' data_17 _database_code_depnum_ccdc_archive 'CCDC 698859' # hphxpy2 _refine_special_details ; The methyl group was refined as a rigid rotor. The hydrogen atom bonded to C17 (H17A) was located in the difference map and added geometrically as to an aromtic carbon. This carbon-hydrogen bond distance was restrained to 0.95(1)\%A while the hydrogen position was refined. ; _audit_creation_method 'enCIFer editing of SHELXL-97 file' _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H15 N O' _chemical_formula_sum 'C16 H15 N O' _chemical_formula_weight 237.29 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 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 9.7651(14) _cell_length_b 14.083(2) _cell_length_c 10.0083(14) _cell_angle_alpha 90.00 _cell_angle_beta 117.807(2) _cell_angle_gamma 90.00 _cell_volume 1217.4(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3833 _cell_measurement_theta_min 2.36 _cell_measurement_theta_max 27.41 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.86 _exptl_crystal_size_mid 0.49 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.295 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 504 _exptl_absorpt_coefficient_mu 0.081 _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 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX CCD area detector' _diffrn_measurement_method omega _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 10460 _diffrn_reflns_av_R_equivalents 0.1063 _diffrn_reflns_av_sigmaI/netI 0.0658 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.36 _diffrn_reflns_theta_max 27.54 _reflns_number_total 2788 _reflns_number_gt 2263 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART version 5.625 (Bruker, 2001)' _computing_cell_refinement 'Bruker SAINT version 6.36A (Bruker, 2002)' _computing_data_reduction 'Bruker SAINT; SHELXTL (Sheldrick, 2008)' _computing_structure_solution 'SHELXTL (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics ' ? ' _computing_publication_material 'enCIFer(Allen et al.,2004);PLATON(Spek,2003)' _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^)+(0.0634P)^2^+0.0510P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary . _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2788 _refine_ls_number_parameters 167 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0587 _refine_ls_R_factor_gt 0.0492 _refine_ls_wR_factor_ref 0.1336 _refine_ls_wR_factor_gt 0.1285 _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_restrained_S_all 1.083 _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 N1 N 0.22058(12) 0.23129(8) 0.73028(12) 0.0285(3) Uani 1 1 d . . . C2 C 0.25354(14) 0.15449(10) 0.66678(14) 0.0259(3) Uani 1 1 d . . . C3 C 0.15196(15) 0.10010(11) 0.54364(15) 0.0326(4) Uani 1 1 d . . . H3A H 0.0452 0.1158 0.4890 0.039 Uiso 1 1 calc R . . C4 C 0.21176(16) 0.02307(11) 0.50409(15) 0.0350(4) Uani 1 1 d . . . H4A H 0.1456 -0.0153 0.4207 0.042 Uiso 1 1 calc R . . C5 C 0.36935(16) 0.00056(10) 0.58550(15) 0.0308(3) Uani 1 1 d . . . H5A H 0.4072 -0.0529 0.5548 0.037 Uiso 1 1 calc R . . C6 C 0.47240(15) 0.05278(10) 0.70879(14) 0.0253(3) Uani 1 1 d . . . C7 C 0.41444(14) 0.13349(9) 0.75290(13) 0.0231(3) Uani 1 1 d . . . C8 C 0.47577(15) 0.20448(9) 0.87189(14) 0.0253(3) Uani 1 1 d . . . C9 C 0.35373(16) 0.25990(10) 0.85354(15) 0.0284(3) Uani 1 1 d . . . H9A H 0.3601 0.3114 0.9175 0.034 Uiso 1 1 calc R . . C10 C 0.06729(16) 0.27235(12) 0.67999(18) 0.0394(4) Uani 1 1 d . . . H10A H 0.0772 0.3343 0.7283 0.059 Uiso 1 1 calc R . . H10B H 0.0051 0.2300 0.7078 0.059 Uiso 1 1 calc R . . H10C H 0.0165 0.2803 0.5700 0.059 Uiso 1 1 calc R . . C11 C 0.64055(16) 0.21861(10) 0.99621(16) 0.0340(4) Uani 1 1 d . . . H11A H 0.6888 0.2733 0.9721 0.041 Uiso 1 1 calc R . . H11B H 0.6408 0.2313 1.0936 0.041 Uiso 1 1 calc R . . C12 C 0.72846(14) 0.12980(10) 1.00671(14) 0.0269(3) Uani 1 1 d . . . C13 C 0.73726(14) 0.10514(10) 0.86635(15) 0.0278(3) Uani 1 1 d . . . C14 C 0.64013(15) 0.01894(10) 0.79094(15) 0.0278(3) Uani 1 1 d . . . H14A H 0.6705 -0.0062 0.7151 0.033 Uiso 1 1 calc R . . C15 C 0.66835(18) -0.05944(10) 0.91081(16) 0.0337(3) Uani 1 1 d . . . H15A H 0.5740 -0.0670 0.9231 0.040 Uiso 1 1 calc R . . H15B H 0.6888 -0.1207 0.8749 0.040 Uiso 1 1 calc R . . C16 C 0.80600(16) -0.03450(11) 1.06420(16) 0.0337(4) Uani 1 1 d . . . H16A H 0.8191 -0.0832 1.1406 0.040 Uiso 1 1 calc R . . H16B H 0.9028 -0.0307 1.0555 0.040 Uiso 1 1 calc R . . C17 C 0.76856(15) 0.06037(11) 1.10832(15) 0.0300(3) Uani 1 1 d D . . H17A H 0.7647(17) 0.0662(11) 1.2017(12) 0.036 Uiso 1 1 d D . . O18 O 0.80793(11) 0.15060(8) 0.81508(11) 0.0409(3) Uani 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 N1 0.0213(6) 0.0318(6) 0.0295(6) 0.0075(5) 0.0094(5) 0.0046(5) C2 0.0217(6) 0.0330(8) 0.0222(6) 0.0068(5) 0.0096(5) -0.0005(5) C3 0.0216(7) 0.0490(9) 0.0230(7) 0.0031(6) 0.0069(6) -0.0063(6) C4 0.0323(8) 0.0465(9) 0.0231(7) -0.0068(6) 0.0104(6) -0.0168(7) C5 0.0362(8) 0.0322(8) 0.0282(7) -0.0046(6) 0.0185(6) -0.0061(6) C6 0.0253(7) 0.0288(7) 0.0231(6) 0.0020(5) 0.0122(6) -0.0012(5) C7 0.0201(6) 0.0265(7) 0.0203(6) 0.0032(5) 0.0074(5) -0.0014(5) C8 0.0235(6) 0.0238(7) 0.0248(6) 0.0028(5) 0.0080(5) 0.0000(5) C9 0.0292(7) 0.0254(7) 0.0292(7) 0.0026(6) 0.0124(6) 0.0017(5) C10 0.0254(7) 0.0488(10) 0.0414(8) 0.0117(7) 0.0133(7) 0.0129(6) C11 0.0254(7) 0.0298(8) 0.0349(8) -0.0060(6) 0.0041(6) -0.0019(6) C12 0.0172(6) 0.0305(8) 0.0254(7) -0.0015(6) 0.0035(5) -0.0033(5) C13 0.0179(6) 0.0324(8) 0.0271(7) 0.0110(6) 0.0055(5) 0.0053(5) C14 0.0280(7) 0.0318(8) 0.0263(7) 0.0013(6) 0.0148(6) 0.0056(6) C15 0.0421(8) 0.0265(8) 0.0348(8) 0.0030(6) 0.0200(7) 0.0063(6) C16 0.0319(7) 0.0379(8) 0.0331(7) 0.0149(6) 0.0167(6) 0.0105(6) C17 0.0221(6) 0.0401(9) 0.0242(7) 0.0018(6) 0.0077(5) -0.0006(6) O18 0.0286(5) 0.0530(7) 0.0383(6) 0.0168(5) 0.0132(5) -0.0034(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C2 1.3668(18) . ? N1 C9 1.3705(18) . ? N1 C10 1.4578(17) . ? C2 C3 1.3961(19) . ? C2 C7 1.4268(17) . ? C3 C4 1.375(2) . ? C3 H3A 0.9500 . ? C4 C5 1.401(2) . ? C4 H4A 0.9500 . ? C5 C6 1.3848(19) . ? C5 H5A 0.9500 . ? C6 C7 1.4283(19) . ? C6 C14 1.5262(18) . ? C7 C8 1.4530(18) . ? C8 C9 1.3634(18) . ? C8 C11 1.5195(18) . ? C9 H9A 0.9500 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C12 1.4928(19) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C17 1.331(2) . ? C12 C13 1.4880(19) . ? C13 O18 1.2164(16) . ? C13 C14 1.508(2) . ? C14 C15 1.557(2) . ? C14 H14A 1.0000 . ? C15 C16 1.537(2) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.505(2) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 H17A 0.957(9) . ? 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 C2 N1 C9 108.72(11) . . ? C2 N1 C10 125.44(12) . . ? C9 N1 C10 125.76(12) . . ? N1 C2 C3 128.33(13) . . ? N1 C2 C7 108.36(11) . . ? C3 C2 C7 123.25(13) . . ? C4 C3 C2 117.69(13) . . ? C4 C3 H3A 121.2 . . ? C2 C3 H3A 121.2 . . ? C3 C4 C5 120.66(13) . . ? C3 C4 H4A 119.7 . . ? C5 C4 H4A 119.7 . . ? C6 C5 C4 122.86(14) . . ? C6 C5 H5A 118.6 . . ? C4 C5 H5A 118.6 . . ? C5 C6 C7 118.03(12) . . ? C5 C6 C14 117.73(12) . . ? C7 C6 C14 124.22(11) . . ? C2 C7 C6 117.50(12) . . ? C2 C7 C8 105.61(11) . . ? C6 C7 C8 136.86(12) . . ? C9 C8 C7 106.46(11) . . ? C9 C8 C11 124.09(12) . . ? C7 C8 C11 129.45(12) . . ? C8 C9 N1 110.83(12) . . ? C8 C9 H9A 124.6 . . ? N1 C9 H9A 124.6 . . ? N1 C10 H10A 109.5 . . ? N1 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? N1 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C12 C11 C8 107.61(11) . . ? C12 C11 H11A 110.2 . . ? C8 C11 H11A 110.2 . . ? C12 C11 H11B 110.2 . . ? C8 C11 H11B 110.2 . . ? H11A C11 H11B 108.5 . . ? C17 C12 C13 115.08(13) . . ? C17 C12 C11 128.59(13) . . ? C13 C12 C11 114.43(11) . . ? O18 C13 C12 124.71(13) . . ? O18 C13 C14 124.09(13) . . ? C12 C13 C14 111.13(11) . . ? C13 C14 C6 106.53(11) . . ? C13 C14 C15 109.94(11) . . ? C6 C14 C15 113.33(11) . . ? C13 C14 H14A 109.0 . . ? C6 C14 H14A 109.0 . . ? C15 C14 H14A 109.0 . . ? C16 C15 C14 111.44(12) . . ? C16 C15 H15A 109.3 . . ? C14 C15 H15A 109.3 . . ? C16 C15 H15B 109.3 . . ? C14 C15 H15B 109.3 . . ? H15A C15 H15B 108.0 . . ? C17 C16 C15 106.08(11) . . ? C17 C16 H16A 110.5 . . ? C15 C16 H16A 110.5 . . ? C17 C16 H16B 110.5 . . ? C15 C16 H16B 110.5 . . ? H16A C16 H16B 108.7 . . ? C12 C17 C16 116.95(13) . . ? C12 C17 H17A 123.5(9) . . ? C16 C17 H17A 119.2(9) . . ? 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 C9 N1 C2 C3 177.04(13) . . . . ? C10 N1 C2 C3 0.3(2) . . . . ? C9 N1 C2 C7 -0.18(14) . . . . ? C10 N1 C2 C7 -176.96(12) . . . . ? N1 C2 C3 C4 -177.28(13) . . . . ? C7 C2 C3 C4 -0.4(2) . . . . ? C2 C3 C4 C5 0.1(2) . . . . ? C3 C4 C5 C6 0.5(2) . . . . ? C4 C5 C6 C7 -0.6(2) . . . . ? C4 C5 C6 C14 178.04(12) . . . . ? N1 C2 C7 C6 177.67(11) . . . . ? C3 C2 C7 C6 0.28(18) . . . . ? N1 C2 C7 C8 -0.71(14) . . . . ? C3 C2 C7 C8 -178.10(12) . . . . ? C5 C6 C7 C2 0.25(18) . . . . ? C14 C6 C7 C2 -178.33(11) . . . . ? C5 C6 C7 C8 177.96(14) . . . . ? C14 C6 C7 C8 -0.6(2) . . . . ? C2 C7 C8 C9 1.33(14) . . . . ? C6 C7 C8 C9 -176.57(14) . . . . ? C2 C7 C8 C11 -178.96(13) . . . . ? C6 C7 C8 C11 3.1(2) . . . . ? C7 C8 C9 N1 -1.50(15) . . . . ? C11 C8 C9 N1 178.77(12) . . . . ? C2 N1 C9 C8 1.08(15) . . . . ? C10 N1 C9 C8 177.85(12) . . . . ? C9 C8 C11 C12 163.65(13) . . . . ? C7 C8 C11 C12 -16.02(19) . . . . ? C8 C11 C12 C17 -102.60(16) . . . . ? C8 C11 C12 C13 60.81(15) . . . . ? C17 C12 C13 O18 -126.69(15) . . . . ? C11 C12 C13 O18 67.59(16) . . . . ? C17 C12 C13 C14 56.24(15) . . . . ? C11 C12 C13 C14 -109.49(13) . . . . ? O18 C13 C14 C6 -99.16(14) . . . . ? C12 C13 C14 C6 77.93(12) . . . . ? O18 C13 C14 C15 137.66(13) . . . . ? C12 C13 C14 C15 -45.24(14) . . . . ? C5 C6 C14 C13 154.65(12) . . . . ? C7 C6 C14 C13 -26.77(16) . . . . ? C5 C6 C14 C15 -84.32(15) . . . . ? C7 C6 C14 C15 94.26(15) . . . . ? C13 C14 C15 C16 -10.16(15) . . . . ? C6 C14 C15 C16 -129.25(13) . . . . ? C14 C15 C16 C17 57.20(15) . . . . ? C13 C12 C17 C16 -4.16(17) . . . . ? C11 C12 C17 C16 159.15(13) . . . . ? C15 C16 C17 C12 -51.83(16) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.29 _refine_diff_density_min -0.25 _refine_diff_density_rms 0.05 data_19 _database_code_depnum_ccdc_archive 'CCDC 698860' # hphxsi3 _audit_creation_method 'enCIFer editing of SHELXL97 CIF output' _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H23 N O Si' _chemical_formula_sum 'C19 H23 N O Si' _chemical_formula_weight 309.47 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 orthorhombic _symmetry_space_group_name_H-M 'P n a 21' _symmetry_space_group_name_Hall 'P 2c -2n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' _cell_length_a 23.565(2) _cell_length_b 10.8079(10) _cell_length_c 6.5185(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1660.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3122 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 26.9 _exptl_crystal_description lath _exptl_crystal_colour colourless _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.238 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 664 _exptl_absorpt_coefficient_mu 0.143 _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 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART1000 CCD area detector' _diffrn_measurement_method omega _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 10391 _diffrn_reflns_av_R_equivalents 0.039 _diffrn_reflns_av_sigmaI/netI 0.054 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3751 _reflns_number_gt 2929 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART version 5.624 (Bruker, 2001)' _computing_cell_refinement 'Bruker SAINT version 6.36A (Bruker, 2002)' _computing_data_reduction 'Bruker SAINT; SHELXTL (Sheldrick, 2008)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics ' ?' _computing_publication_material 'enCIFer (Allen et al., 2004); PLATON (Spek,2003)' _refine_special_details ; ; _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^)+(0.034P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary . _atom_sites_solution_hydrogens 'Me H atoms from delta-F; others placed geometrically' _refine_ls_hydrogen_treatment 'rigid rotor; riding model' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.38(11) _refine_ls_number_reflns 3751 _refine_ls_number_parameters 204 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0502 _refine_ls_R_factor_gt 0.0349 _refine_ls_wR_factor_ref 0.0741 _refine_ls_wR_factor_gt 0.0694 _refine_ls_goodness_of_fit_ref 0.93 _refine_ls_restrained_S_all 0.93 _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 N1 N 1.02117(6) 0.86689(14) -0.0810(3) 0.0260(4) Uani 1 1 d . . . C2 C 1.03563(7) 0.81649(16) 0.1053(3) 0.0243(4) Uani 1 1 d . . . C3 C 1.08427(8) 0.82809(19) 0.2267(4) 0.0306(5) Uani 1 1 d . . . H3 H 1.1149 0.8798 0.1864 0.037 Uiso 1 1 calc R . . C4 C 1.08605(8) 0.76177(19) 0.4069(3) 0.0337(5) Uani 1 1 d . . . H4 H 1.1194 0.7651 0.4886 0.040 Uiso 1 1 calc R . . C5 C 1.04020(7) 0.68944(19) 0.4738(3) 0.0288(5) Uani 1 1 d . . . H5 H 1.0426 0.6470 0.6011 0.035 Uiso 1 1 calc R . . C6 C 0.99156(7) 0.67931(17) 0.3559(3) 0.0226(4) Uani 1 1 d . . . C7 C 0.99024(7) 0.73963(17) 0.1660(3) 0.0212(4) Uani 1 1 d . . . C8 C 0.94818(7) 0.74212(17) 0.0065(3) 0.0211(4) Uani 1 1 d . . . C9 C 0.96866(7) 0.82209(18) -0.1385(3) 0.0246(4) Uani 1 1 d . . . H9 H 0.9494 0.8438 -0.2614 0.030 Uiso 1 1 calc R . . C10 C 1.05478(9) 0.95789(19) -0.1927(3) 0.0360(5) Uani 1 1 d . . . H10A H 1.0946 0.9318 -0.1947 0.054 Uiso 1 1 calc R . . H10B H 1.0517 1.0385 -0.1247 0.054 Uiso 1 1 calc R . . H10C H 1.0407 0.9645 -0.3337 0.054 Uiso 1 1 calc R . . C11 C 0.89834(7) 0.65476(18) -0.0127(3) 0.0235(4) Uani 1 1 d . . . H11A H 0.9134 0.5700 -0.0314 0.028 Uiso 1 1 calc R . . H11B H 0.8774 0.6765 -0.1393 0.028 Uiso 1 1 calc R . . C12 C 0.85431(7) 0.65160(17) 0.1711(3) 0.0222(4) Uani 1 1 d . . . C13 C 0.88677(7) 0.69837(18) 0.3549(3) 0.0216(4) Uani 1 1 d . . . C14 C 0.93715(7) 0.61785(18) 0.4059(3) 0.0234(4) Uani 1 1 d . . . C15 C 0.92498(8) 0.49984(18) 0.4400(3) 0.0299(5) Uani 1 1 d . . . H15 H 0.9537 0.4419 0.4746 0.036 Uiso 1 1 calc R . . C16 C 0.86364(8) 0.46112(19) 0.4216(4) 0.0361(5) Uani 1 1 d . . . H16A H 0.8423 0.4908 0.5428 0.043 Uiso 1 1 calc R . . H16B H 0.8612 0.3697 0.4187 0.043 Uiso 1 1 calc R . . C17 C 0.83657(8) 0.51486(18) 0.2235(3) 0.0273(4) Uani 1 1 d . . . H17A H 0.7948 0.5116 0.2377 0.033 Uiso 1 1 calc R . . H17B H 0.8471 0.4611 0.1065 0.033 Uiso 1 1 calc R . . O18 O 0.87523(5) 0.79197(12) 0.4515(2) 0.0273(3) Uani 1 1 d . . . Si19 Si 0.790162(19) 0.75034(6) 0.10449(10) 0.02446(12) Uani 1 1 d . . . C20 C 0.75007(8) 0.6659(2) -0.1017(4) 0.0399(6) Uani 1 1 d . . . H20A H 0.7191 0.7182 -0.1518 0.060 Uiso 1 1 calc R . . H20B H 0.7344 0.5890 -0.0455 0.060 Uiso 1 1 calc R . . H20C H 0.7758 0.6465 -0.2153 0.060 Uiso 1 1 calc R . . C21 C 0.81320(8) 0.90363(19) 0.0031(4) 0.0360(5) Uani 1 1 d . . . H21A H 0.7800 0.9571 -0.0149 0.054 Uiso 1 1 calc R . . H21B H 0.8322 0.8922 -0.1294 0.054 Uiso 1 1 calc R . . H21C H 0.8396 0.9422 0.1002 0.054 Uiso 1 1 calc R . . C22 C 0.74239(8) 0.7716(2) 0.3305(3) 0.0345(5) Uani 1 1 d . . . H22A H 0.7081 0.8162 0.2879 0.052 Uiso 1 1 calc R . . H22B H 0.7622 0.8194 0.4364 0.052 Uiso 1 1 calc R . . H22C H 0.7318 0.6906 0.3858 0.052 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 N1 0.0245(8) 0.0247(9) 0.0288(9) 0.0044(8) 0.0054(7) -0.0009(7) C2 0.0231(9) 0.0219(9) 0.0279(10) -0.0027(11) 0.0034(9) 0.0055(8) C3 0.0206(10) 0.0334(13) 0.0378(13) -0.0037(10) 0.0031(9) 0.0007(9) C4 0.0201(9) 0.0445(13) 0.0367(12) -0.0055(11) -0.0053(9) 0.0054(9) C5 0.0254(10) 0.0345(12) 0.0264(11) -0.0004(9) -0.0004(9) 0.0091(9) C6 0.0234(9) 0.0202(10) 0.0242(10) -0.0011(8) 0.0033(8) 0.0071(8) C7 0.0186(9) 0.0217(10) 0.0231(11) -0.0038(8) 0.0020(7) 0.0043(8) C8 0.0221(9) 0.0213(10) 0.0200(9) -0.0006(8) 0.0038(7) 0.0039(8) C9 0.0242(9) 0.0265(11) 0.0230(10) -0.0021(9) 0.0012(8) 0.0024(8) C10 0.0365(11) 0.0306(12) 0.0409(13) 0.0061(10) 0.0081(10) -0.0078(10) C11 0.0243(9) 0.0233(11) 0.0230(11) -0.0024(9) -0.0009(8) 0.0007(8) C12 0.0222(9) 0.0214(10) 0.0229(10) -0.0012(8) 0.0006(7) -0.0004(8) C13 0.0205(9) 0.0218(10) 0.0227(10) 0.0053(9) 0.0043(8) -0.0022(8) C14 0.0251(9) 0.0269(10) 0.0183(10) 0.0013(8) -0.0002(8) 0.0050(8) C15 0.0359(11) 0.0268(11) 0.0271(11) 0.0041(9) -0.0019(9) 0.0064(9) C16 0.0428(12) 0.0257(11) 0.0399(12) 0.0092(10) -0.0002(10) -0.0072(10) C17 0.0247(10) 0.0238(11) 0.0333(11) 0.0021(10) 0.0023(9) -0.0024(8) O18 0.0263(7) 0.0272(7) 0.0283(8) -0.0062(7) 0.0002(6) 0.0030(6) Si19 0.0204(2) 0.0264(3) 0.0265(2) 0.0002(3) -0.0019(2) 0.0016(2) C20 0.0334(11) 0.0444(14) 0.0418(14) -0.0053(12) -0.0094(10) 0.0017(11) C21 0.0315(11) 0.0317(12) 0.0447(13) 0.0078(11) -0.0047(10) 0.0054(9) C22 0.0244(10) 0.0417(14) 0.0374(12) -0.0013(11) 0.0022(9) 0.0055(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 N1 C2 1.374(2) . ? N1 C9 1.381(2) . ? N1 C10 1.458(2) . ? C2 C3 1.398(3) . ? C2 C7 1.411(2) . ? C3 C4 1.376(3) . ? C3 H3 0.9500 . ? C4 C5 1.403(3) . ? C4 H4 0.9500 . ? C5 C6 1.384(2) . ? C5 H5 0.9500 . ? C6 C7 1.400(3) . ? C6 C14 1.480(2) . ? C7 C8 1.436(2) . ? C8 C9 1.369(3) . ? C8 C11 1.512(2) . ? C9 H9 0.9500 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C12 1.585(3) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.509(3) . ? C12 C17 1.573(3) . ? C12 Si19 1.9006(18) . ? C13 O18 1.222(2) . ? C13 C14 1.509(2) . ? C14 C15 1.326(3) . ? C15 C16 1.510(3) . ? C15 H15 0.9500 . ? C16 C17 1.553(3) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? Si19 C21 1.864(2) . ? Si19 C22 1.868(2) . ? Si19 C20 1.879(2) . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 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 C2 N1 C9 108.85(15) . . ? C2 N1 C10 125.05(16) . . ? C9 N1 C10 126.02(17) . . ? N1 C2 C3 131.90(18) . . ? N1 C2 C7 107.04(16) . . ? C3 C2 C7 121.05(19) . . ? C4 C3 C2 117.45(19) . . ? C4 C3 H3 121.3 . . ? C2 C3 H3 121.3 . . ? C3 C4 C5 122.13(19) . . ? C3 C4 H4 118.9 . . ? C5 C4 H4 118.9 . . ? C6 C5 C4 120.61(19) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C5 C6 C7 118.20(17) . . ? C5 C6 C14 129.07(18) . . ? C7 C6 C14 112.63(16) . . ? C6 C7 C2 120.34(17) . . ? C6 C7 C8 131.62(17) . . ? C2 C7 C8 108.02(17) . . ? C9 C8 C7 105.56(16) . . ? C9 C8 C11 127.68(18) . . ? C7 C8 C11 125.73(17) . . ? C8 C9 N1 110.50(17) . . ? C8 C9 H9 124.8 . . ? N1 C9 H9 124.8 . . ? N1 C10 H10A 109.5 . . ? N1 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? N1 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C8 C11 C12 117.36(15) . . ? C8 C11 H11A 108.0 . . ? C12 C11 H11A 108.0 . . ? C8 C11 H11B 108.0 . . ? C12 C11 H11B 108.0 . . ? H11A C11 H11B 107.2 . . ? C13 C12 C17 106.09(15) . . ? C13 C12 C11 105.13(13) . . ? C17 C12 C11 110.99(15) . . ? C13 C12 Si19 113.36(13) . . ? C17 C12 Si19 111.45(12) . . ? C11 C12 Si19 109.63(12) . . ? O18 C13 C12 125.01(16) . . ? O18 C13 C14 122.59(16) . . ? C12 C13 C14 112.38(16) . . ? C15 C14 C6 130.99(17) . . ? C15 C14 C13 114.92(16) . . ? C6 C14 C13 111.96(15) . . ? C14 C15 C16 117.42(17) . . ? C14 C15 H15 121.3 . . ? C16 C15 H15 121.3 . . ? C15 C16 C17 110.83(17) . . ? C15 C16 H16A 109.5 . . ? C17 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? C17 C16 H16B 109.5 . . ? H16A C16 H16B 108.1 . . ? C16 C17 C12 115.00(16) . . ? C16 C17 H17A 108.5 . . ? C12 C17 H17A 108.5 . . ? C16 C17 H17B 108.5 . . ? C12 C17 H17B 108.5 . . ? H17A C17 H17B 107.5 . . ? C21 Si19 C22 110.21(10) . . ? C21 Si19 C20 108.93(11) . . ? C22 Si19 C20 108.72(9) . . ? C21 Si19 C12 110.39(8) . . ? C22 Si19 C12 111.61(9) . . ? C20 Si19 C12 106.88(9) . . ? Si19 C20 H20A 109.5 . . ? Si19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? Si19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? Si19 C21 H21A 109.5 . . ? Si19 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? Si19 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? Si19 C22 H22A 109.5 . . ? Si19 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? Si19 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 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 C9 N1 C2 C3 177.8(2) . . . . ? C10 N1 C2 C3 -5.3(3) . . . . ? C9 N1 C2 C7 -0.86(19) . . . . ? C10 N1 C2 C7 176.08(17) . . . . ? N1 C2 C3 C4 -178.49(19) . . . . ? C7 C2 C3 C4 0.0(3) . . . . ? C2 C3 C4 C5 -3.0(3) . . . . ? C3 C4 C5 C6 2.0(3) . . . . ? C4 C5 C6 C7 2.1(3) . . . . ? C4 C5 C6 C14 -173.98(18) . . . . ? C5 C6 C7 C2 -5.0(3) . . . . ? C14 C6 C7 C2 171.70(16) . . . . ? C5 C6 C7 C8 176.50(19) . . . . ? C14 C6 C7 C8 -6.8(3) . . . . ? N1 C2 C7 C6 -177.13(16) . . . . ? C3 C2 C7 C6 4.0(3) . . . . ? N1 C2 C7 C8 1.7(2) . . . . ? C3 C2 C7 C8 -177.15(17) . . . . ? C6 C7 C8 C9 176.76(18) . . . . ? C2 C7 C8 C9 -1.9(2) . . . . ? C6 C7 C8 C11 -14.2(3) . . . . ? C2 C7 C8 C11 167.20(16) . . . . ? C7 C8 C9 N1 1.4(2) . . . . ? C11 C8 C9 N1 -167.42(16) . . . . ? C2 N1 C9 C8 -0.3(2) . . . . ? C10 N1 C9 C8 -177.24(17) . . . . ? C9 C8 C11 C12 -133.67(19) . . . . ? C7 C8 C11 C12 59.7(2) . . . . ? C8 C11 C12 C13 -23.1(2) . . . . ? C8 C11 C12 C17 -137.40(17) . . . . ? C8 C11 C12 Si19 99.05(16) . . . . ? C17 C12 C13 O18 -124.67(19) . . . . ? C11 C12 C13 O18 117.68(19) . . . . ? Si19 C12 C13 O18 -2.0(2) . . . . ? C17 C12 C13 C14 56.84(18) . . . . ? C11 C12 C13 C14 -60.81(19) . . . . ? Si19 C12 C13 C14 179.46(12) . . . . ? C5 C6 C14 C15 -64.6(3) . . . . ? C7 C6 C14 C15 119.1(2) . . . . ? C5 C6 C14 C13 133.2(2) . . . . ? C7 C6 C14 C13 -43.1(2) . . . . ? O18 C13 C14 C15 124.7(2) . . . . ? C12 C13 C14 C15 -56.8(2) . . . . ? O18 C13 C14 C6 -70.0(2) . . . . ? C12 C13 C14 C6 108.50(17) . . . . ? C6 C14 C15 C16 -161.2(2) . . . . ? C13 C14 C15 C16 0.6(3) . . . . ? C14 C15 C16 C17 46.2(3) . . . . ? C15 C16 C17 C12 -40.1(2) . . . . ? C13 C12 C17 C16 -8.9(2) . . . . ? C11 C12 C17 C16 104.81(19) . . . . ? Si19 C12 C17 C16 -132.70(15) . . . . ? C13 C12 Si19 C21 69.46(15) . . . . ? C17 C12 Si19 C21 -170.94(14) . . . . ? C11 C12 Si19 C21 -47.66(15) . . . . ? C13 C12 Si19 C22 -53.47(15) . . . . ? C17 C12 Si19 C22 66.13(15) . . . . ? C11 C12 Si19 C22 -170.59(12) . . . . ? C13 C12 Si19 C20 -172.22(13) . . . . ? C17 C12 Si19 C20 -52.62(15) . . . . ? C11 C12 Si19 C20 70.66(14) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.21 _refine_diff_density_min -0.20 _refine_diff_density_rms 0.04 #===END of CIF