# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 207/378 data_global #======================================================== # 1. SUBMISSION DETAILS _publ_contact_author # Name and address of author for correspondence ; Dr. Richard Wightman Department of Chemistry Heriot-Watt University Edinburgh EH14 4AS ; _publ_contact_author_phone '0131 451-8039' _publ_contact_author_fax '0131 451 3180' _publ_contact_author_email R.Wightman@hw.ac.uk _publ_requested_journal 'J. Chem. Soc., Perkin Trans.I' _publ_requested_coeditor_name ? _publ_contact_letter ; ; #======================================================================= # 2. PROCESSING SUMMARY (IUCr Office Use Only) _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_date_printers_first ? _journal_date_printers_final ? _journal_date_proofs_out ? _journal_date_proofs_in ? _journal_coeditor_name ? _journal_coeditor_code ? _journal_coeditor_notes ; ? ; _journal_techeditor_code ? _journal_techeditor_notes ; ? ; _journal_coden_ASTM ? _journal_name_full ? _journal_year ? _journal_volume ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? #======================================================================= # 3. TITLE AND AUTHOR LIST _publ_section_title ; a-Chloronitroso compounds derived from carbohydrate ketones: cyloadditions with cyclic dienes, a synthesis of (-)-physoperuvine and a formal synthesis of (+)-epibatidine ; # The loop structure below should contain the names and addresses of all # authors, in the required order of publication. Repeat as necessary. loop_ _publ_author_name _publ_author_address 'Wightman, Richard.' #<--'Last name, first name' ; Department of Chemistry Heriot-Watt University Edinburgh EH14 4AS ; 'Hall, Adrian' ; Department of Chemistry Heriot-Watt University Edinburgh EH14 4AS ; 'Bailey, Patrick D. ' ; Department of Chemistry Heriot-Watt University Edinburgh EH14 4AS ; 'Rees, David C.' ; Organon Laboratories Ltd. Newhouse Lanarkshire MK1 5SH ; 'Rosair, Georgina M.' ; Department of Chemistry Heriot-Watt University Edinburgh EH14 4AS ; 'Wightman, Richard H.' ; Department of Chemistry Heriot-Watt University Edinburgh EH14 4AS ; #======================================================================= data_8 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H18 Cl N O6' _chemical_formula_weight 307.72 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' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 6.7596(7) _cell_length_b 8.7092(10) _cell_length_c 26.1866(19) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1541.6(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 27 _cell_measurement_theta_min 4.93 _cell_measurement_theta_max 12.16 _exptl_crystal_description traingular_plate _exptl_crystal_colour blue _exptl_crystal_size_max 0.54 _exptl_crystal_size_mid 0.42 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.326 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 0.270 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7271 _exptl_absorpt_correction_T_max 0.7704 _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 '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 10.32 _diffrn_reflns_number 3810 _diffrn_reflns_av_R_equivalents 0.0438 _diffrn_reflns_av_sigmaI/netI 0.0756 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 2.46 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2670 _reflns_number_gt 1487 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens 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^)+(0.0490P)^2^+0.1769P] 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 SHELXL _refine_ls_extinction_coef 0.0090(16) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.27(19) _refine_ls_number_reflns 2670 _refine_ls_number_parameters 183 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1161 _refine_ls_R_factor_gt 0.0562 _refine_ls_wR_factor_ref 0.1478 _refine_ls_wR_factor_gt 0.1194 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.006 _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 Cl1 Cl 0.6606(3) -0.0970(3) 0.87628(6) 0.1088(7) Uani 1 1 d . . . O1 O 0.3679(7) 0.1688(4) 0.83648(13) 0.0802(12) Uani 1 1 d . . . N1 N 0.2958(12) -0.2344(5) 0.86221(17) 0.100(2) Uani 1 1 d . . . C1 C 0.4247(8) 0.1102(6) 0.78924(17) 0.0646(12) Uani 1 1 d . . . H1B H 0.5554 0.1498 0.7798 0.078 Uiso 1 1 calc R . . O2 O 0.2908(6) 0.1397(4) 0.75077(14) 0.0823(11) Uani 1 1 d . . . C2 C 0.4320(8) -0.0637(6) 0.79407(17) 0.0597(12) Uani 1 1 d . . . H2A H 0.5512 -0.1083 0.7788 0.072 Uiso 1 1 calc R . . C3 C 0.4182(8) -0.0921(6) 0.85168(18) 0.0662(13) Uani 1 1 d . . . O3 O 0.2566(5) -0.1132(4) 0.76995(11) 0.0626(9) Uani 1 1 d . . . C4 C 0.3033(9) 0.0472(5) 0.86926(16) 0.0647(13) Uani 1 1 d . . . H4A H 0.1624 0.0288 0.8630 0.078 Uiso 1 1 calc R . . O4 O 0.3844(12) -0.3329(7) 0.8808(2) 0.153(3) Uani 1 1 d . . . O5 O 0.2921(7) -0.0301(5) 0.95574(13) 0.0934(13) Uani 1 1 d . . . C5 C 0.3286(10) 0.0993(7) 0.92443(18) 0.0806(15) Uani 1 1 d . . . H5A H 0.4633 0.1374 0.9300 0.097 Uiso 1 1 calc R . . O6 O 0.0287(7) 0.1300(6) 0.96412(15) 0.0977(14) Uani 1 1 d . . . C6 C 0.1805(14) 0.2170(7) 0.9413(2) 0.103(2) Uani 1 1 d . . . H6A H 0.2386 0.2877 0.9656 0.123 Uiso 1 1 calc R . . H6B H 0.1306 0.2747 0.9123 0.123 Uiso 1 1 calc R . . C7 C 0.1844(7) 0.0044(5) 0.73661(17) 0.0619(12) Uani 1 1 d . . . C8 C -0.0305(8) 0.0262(8) 0.7452(3) 0.102(2) Uani 1 1 d . . . H8A H -0.1001 -0.0653 0.7354 0.153 Uiso 1 1 calc R . . H8B H -0.0766 0.1111 0.7251 0.153 Uiso 1 1 calc R . . H8C H -0.0541 0.0469 0.7807 0.153 Uiso 1 1 calc R . . C9 C 0.2339(12) -0.0340(7) 0.6822(2) 0.108(2) Uani 1 1 d . . . H9A H 0.1634 -0.1248 0.6721 0.162 Uiso 1 1 calc R . . H9B H 0.3736 -0.0517 0.6791 0.162 Uiso 1 1 calc R . . H9C H 0.1963 0.0499 0.6605 0.162 Uiso 1 1 calc R . . C10 C 0.1244(9) 0.0036(7) 0.9878(2) 0.0820(17) Uani 1 1 d . . . C11 C 0.2011(10) 0.0437(7) 1.04025(18) 0.0931(19) Uani 1 1 d . . . H11A H 0.2646 -0.0444 1.0550 0.140 Uiso 1 1 calc R . . H11B H 0.0928 0.0749 1.0616 0.140 Uiso 1 1 calc R . . H11C H 0.2947 0.1263 1.0376 0.140 Uiso 1 1 calc R . . C12 C -0.0131(12) -0.1299(9) 0.9886(3) 0.123(3) Uani 1 1 d . . . H12A H 0.0507 -0.2156 1.0047 0.185 Uiso 1 1 calc R . . H12B H -0.0487 -0.1568 0.9543 0.185 Uiso 1 1 calc R . . H12C H -0.1301 -0.1032 1.0074 0.185 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 Cl1 0.0841(10) 0.1427(16) 0.0995(10) -0.0066(11) -0.0362(9) 0.0246(12) O1 0.114(3) 0.060(2) 0.066(2) 0.0024(17) 0.009(2) -0.004(2) N1 0.190(7) 0.048(2) 0.063(2) 0.018(2) -0.023(4) 0.016(4) C1 0.067(3) 0.067(3) 0.060(3) 0.008(3) -0.003(3) -0.010(3) O2 0.094(3) 0.061(2) 0.091(2) 0.0166(19) -0.021(2) -0.010(2) C2 0.054(3) 0.067(3) 0.058(3) 0.003(2) 0.002(2) 0.008(3) C3 0.069(3) 0.067(3) 0.063(3) 0.007(3) -0.012(2) 0.003(3) O3 0.071(2) 0.0560(18) 0.0611(16) 0.0090(16) -0.0128(15) -0.0025(19) C4 0.078(3) 0.060(3) 0.056(2) 0.004(2) -0.002(3) -0.003(3) O4 0.246(8) 0.106(4) 0.107(3) 0.013(3) -0.003(5) 0.004(5) O5 0.132(4) 0.083(3) 0.065(2) 0.015(2) 0.010(2) 0.018(3) C5 0.104(4) 0.074(3) 0.063(3) 0.003(3) -0.003(3) -0.005(4) O6 0.113(4) 0.100(3) 0.079(2) 0.021(3) 0.002(2) 0.013(3) C6 0.151(7) 0.084(4) 0.073(4) -0.004(3) 0.013(5) 0.010(5) C7 0.064(3) 0.060(3) 0.062(3) 0.005(2) -0.005(2) -0.001(3) C8 0.066(4) 0.102(5) 0.138(6) 0.017(5) -0.008(4) 0.009(4) C9 0.168(7) 0.093(4) 0.063(3) 0.014(3) 0.006(4) 0.006(5) C10 0.096(5) 0.087(4) 0.063(3) 0.008(3) -0.003(3) -0.002(4) C11 0.112(5) 0.106(5) 0.062(3) 0.000(3) -0.005(3) -0.003(4) C12 0.133(7) 0.130(6) 0.107(5) 0.021(5) -0.039(5) -0.040(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 Cl1 C3 1.761(5) . ? O1 C1 1.393(6) . ? O1 C4 1.432(5) . ? N1 O4 1.153(8) . ? N1 C3 1.515(8) . ? C1 O2 1.378(6) . ? C1 C2 1.520(7) . ? O2 C7 1.430(6) . ? C2 O3 1.411(6) . ? C2 C3 1.532(6) . ? C3 C4 1.512(7) . ? O3 C7 1.431(5) . ? C4 C5 1.524(7) . ? O5 C5 1.415(6) . ? O5 C10 1.440(7) . ? C5 C6 1.499(9) . ? O6 C6 1.409(9) . ? O6 C10 1.420(7) . ? C7 C8 1.482(7) . ? C7 C9 1.502(7) . ? C10 C12 1.489(9) . ? C10 C11 1.509(7) . ? 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 C1 O1 C4 110.2(4) . . ? O4 N1 C3 113.7(7) . . ? O2 C1 O1 113.6(4) . . ? O2 C1 C2 105.5(4) . . ? O1 C1 C2 107.5(4) . . ? C1 O2 C7 111.5(4) . . ? O3 C2 C1 103.9(4) . . ? O3 C2 C3 109.9(4) . . ? C1 C2 C3 103.9(4) . . ? C4 C3 N1 108.7(4) . . ? C4 C3 C2 101.6(4) . . ? N1 C3 C2 110.2(4) . . ? C4 C3 Cl1 112.7(4) . . ? N1 C3 Cl1 114.9(4) . . ? C2 C3 Cl1 107.9(4) . . ? C2 O3 C7 109.9(3) . . ? O1 C4 C3 104.7(4) . . ? O1 C4 C5 108.3(4) . . ? C3 C4 C5 118.0(4) . . ? C5 O5 C10 108.2(5) . . ? O5 C5 C6 104.9(5) . . ? O5 C5 C4 107.0(4) . . ? C6 C5 C4 114.0(5) . . ? C6 O6 C10 105.7(5) . . ? O6 C6 C5 104.1(5) . . ? O2 C7 O3 105.1(3) . . ? O2 C7 C8 110.4(5) . . ? O3 C7 C8 109.5(4) . . ? O2 C7 C9 108.5(5) . . ? O3 C7 C9 110.1(4) . . ? C8 C7 C9 113.0(5) . . ? O6 C10 O5 105.2(4) . . ? O6 C10 C12 109.1(5) . . ? O5 C10 C12 109.9(6) . . ? O6 C10 C11 112.0(5) . . ? O5 C10 C11 107.9(5) . . ? C12 C10 C11 112.4(5) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.235 _refine_diff_density_min -0.167 _refine_diff_density_rms 0.034 #===END data_17 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H30 Cl N O5 Si' _chemical_formula_weight 476.03 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' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 9.9200(10) _cell_length_b 10.1030(10) _cell_length_c 25.963(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2602.1(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 27 _cell_measurement_theta_min 4.59 _cell_measurement_theta_max 10.88 _exptl_crystal_description rectangular_block _exptl_crystal_colour royal_blue _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.215 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1008 _exptl_absorpt_coefficient_mu 0.225 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7600 _exptl_absorpt_correction_T_max 0.7809 _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 'Siemens P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 7.01 _diffrn_reflns_number 3349 _diffrn_reflns_av_R_equivalents 0.0313 _diffrn_reflns_av_sigmaI/netI 0.0966 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -1 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3143 _reflns_number_gt 1765 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens 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^)+(0.0284P)^2^+0.0000P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.2(2) _refine_ls_number_reflns 3143 _refine_ls_number_parameters 290 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1265 _refine_ls_R_factor_gt 0.0582 _refine_ls_wR_factor_ref 0.1201 _refine_ls_wR_factor_gt 0.0972 _refine_ls_goodness_of_fit_ref 1.011 _refine_ls_restrained_S_all 1.011 _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 0.73282(18) 0.25529(19) 0.15148(6) 0.0485(4) Uani 1 1 d . . . Cl1 Cl 0.7942(2) 0.7642(2) 0.12909(6) 0.0833(7) Uani 1 1 d . . . O1 O 0.5899(4) 0.6298(5) 0.05143(19) 0.0624(14) Uani 1 1 d . . . O2 O 0.7325(5) 0.4193(4) 0.15025(17) 0.0519(11) Uani 1 1 d . . . O3 O 0.8477(4) 0.6319(5) -0.01164(16) 0.0592(14) Uani 1 1 d . . . O4 O 0.6335(5) 0.6932(7) -0.03316(18) 0.082(2) Uani 1 1 d . . . O5 O 1.0136(5) 0.5968(7) 0.1181(2) 0.0856(19) Uani 1 1 d . . . N1 N 0.9413(6) 0.5679(7) 0.0839(2) 0.0609(18) Uani 1 1 d . . . C1 C 0.8120(6) 0.6448(6) 0.0800(2) 0.0475(15) Uani 1 1 d . . . C2 C 0.8019(6) 0.7165(7) 0.0281(2) 0.0507(17) Uani 1 1 d . . . H2A H 0.8460 0.8033 0.0280 0.061 Uiso 1 1 calc R . . C3 C 0.6486(6) 0.7240(8) 0.0184(2) 0.0536(19) Uani 1 1 d . . . H3A H 0.6142 0.8129 0.0257 0.064 Uiso 1 1 calc R . . C4 C 0.6917(7) 0.5512(7) 0.0757(2) 0.0485(16) Uani 1 1 d . . . H4A H 0.7157 0.4777 0.0528 0.058 Uiso 1 1 calc R . . C5 C 0.7532(7) 0.6369(8) -0.0539(2) 0.065(2) Uani 1 1 d . . . C6 C 0.7272(10) 0.4959(8) -0.0713(3) 0.094(3) Uani 1 1 d . . . H6A H 0.8086 0.4591 -0.0853 0.141 Uiso 1 1 calc R . . H6B H 0.6581 0.4955 -0.0972 0.141 Uiso 1 1 calc R . . H6C H 0.6986 0.4437 -0.0424 0.141 Uiso 1 1 calc R . . C7 C 0.8078(8) 0.7251(8) -0.0959(2) 0.077(2) Uani 1 1 d . . . H7A H 0.8882 0.6866 -0.1100 0.115 Uiso 1 1 calc R . . H7B H 0.8283 0.8107 -0.0819 0.115 Uiso 1 1 calc R . . H7C H 0.7415 0.7342 -0.1227 0.115 Uiso 1 1 calc R . . C8 C 0.6337(7) 0.4958(7) 0.1248(3) 0.0565(19) Uani 1 1 d . . . H8A H 0.6046 0.5676 0.1469 0.068 Uiso 1 1 calc R . . H8B H 0.5560 0.4412 0.1169 0.068 Uiso 1 1 calc R . . C10 C 0.7380(7) 0.1865(6) 0.0840(2) 0.0527(17) Uani 1 1 d . . . C11 C 0.8536(8) 0.1568(10) 0.0578(3) 0.081(3) Uani 1 1 d . . . H11A H 0.9364 0.1700 0.0738 0.097 Uiso 1 1 calc R . . C12 C 0.8507(11) 0.1075(10) 0.0078(4) 0.094(3) Uani 1 1 d . . . H12A H 0.9309 0.0854 -0.0087 0.113 Uiso 1 1 calc R . . C13 C 0.7281(11) 0.0910(8) -0.0178(3) 0.087(3) Uani 1 1 d . . . H13A H 0.7251 0.0588 -0.0513 0.104 Uiso 1 1 calc R . . C14 C 0.6135(10) 0.1233(10) 0.0078(3) 0.086(3) Uani 1 1 d . . . H14A H 0.5309 0.1143 -0.0088 0.103 Uiso 1 1 calc R . . C15 C 0.6167(8) 0.1697(10) 0.0583(3) 0.076(3) Uani 1 1 d . . . H15A H 0.5363 0.1896 0.0751 0.091 Uiso 1 1 calc R . . C20 C 0.5711(7) 0.2003(7) 0.1813(3) 0.0513(19) Uani 1 1 d . . . C21 C 0.5229(8) 0.0692(8) 0.1776(3) 0.058(2) Uani 1 1 d . . . H21A H 0.5705 0.0078 0.1581 0.070 Uiso 1 1 calc R . . C22 C 0.4078(9) 0.0315(9) 0.2021(3) 0.078(3) Uani 1 1 d . . . H22A H 0.3770 -0.0549 0.1982 0.093 Uiso 1 1 calc R . . C23 C 0.3358(9) 0.1185(9) 0.2324(3) 0.077(3) Uani 1 1 d . . . H23A H 0.2588 0.0904 0.2497 0.092 Uiso 1 1 calc R . . C24 C 0.3795(8) 0.2478(9) 0.2367(3) 0.072(2) Uani 1 1 d . . . H24A H 0.3316 0.3079 0.2568 0.087 Uiso 1 1 calc R . . C25 C 0.4943(8) 0.2872(7) 0.2112(2) 0.0597(19) Uani 1 1 d . . . H25A H 0.5218 0.3749 0.2139 0.072 Uiso 1 1 calc R . . C30 C 0.8822(8) 0.2111(7) 0.1929(3) 0.061(2) Uani 1 1 d . . . C31 C 1.0096(7) 0.2837(9) 0.1755(4) 0.100(3) Uani 1 1 d . . . H31A H 0.9933 0.3774 0.1756 0.149 Uiso 1 1 calc R . . H31B H 1.0333 0.2558 0.1414 0.149 Uiso 1 1 calc R . . H31C H 1.0822 0.2636 0.1987 0.149 Uiso 1 1 calc R . . C32 C 0.9054(10) 0.0604(8) 0.1931(4) 0.086(3) Uani 1 1 d . . . H32A H 0.8245 0.0165 0.2039 0.129 Uiso 1 1 calc R . . H32B H 0.9773 0.0393 0.2165 0.129 Uiso 1 1 calc R . . H32C H 0.9291 0.0316 0.1590 0.129 Uiso 1 1 calc R . . C33 C 0.8496(9) 0.2546(10) 0.2492(3) 0.095(3) Uani 1 1 d . . . H33A H 0.7699 0.2098 0.2608 0.143 Uiso 1 1 calc R . . H33B H 0.8349 0.3485 0.2501 0.143 Uiso 1 1 calc R . . H33C H 0.9239 0.2323 0.2712 0.143 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 0.0471(10) 0.0441(9) 0.0545(9) -0.0024(10) -0.0040(9) -0.0002(11) Cl1 0.1183(17) 0.0645(12) 0.0670(11) -0.0252(10) 0.0115(11) -0.0149(15) O1 0.041(2) 0.071(4) 0.075(3) 0.021(3) -0.003(2) 0.004(3) O2 0.052(3) 0.042(2) 0.062(2) 0.001(2) -0.008(3) 0.001(2) O3 0.047(3) 0.084(4) 0.047(2) 0.001(3) 0.003(2) 0.007(3) O4 0.046(3) 0.141(6) 0.058(3) 0.010(3) -0.005(2) 0.020(3) O5 0.065(3) 0.111(5) 0.081(4) 0.022(4) -0.031(3) -0.019(4) N1 0.035(3) 0.083(5) 0.065(4) 0.011(4) 0.001(3) 0.001(3) C1 0.052(4) 0.036(3) 0.054(4) -0.008(3) 0.005(3) 0.001(4) C2 0.040(3) 0.052(4) 0.060(4) 0.004(3) 0.004(3) 0.000(3) C3 0.047(4) 0.054(5) 0.059(4) 0.011(4) 0.005(3) 0.015(4) C4 0.042(4) 0.051(4) 0.053(4) 0.003(3) 0.000(3) 0.010(4) C5 0.051(4) 0.092(5) 0.052(4) 0.001(4) 0.000(4) -0.010(5) C6 0.101(8) 0.092(6) 0.090(6) -0.005(5) 0.002(6) -0.026(6) C7 0.077(5) 0.096(6) 0.058(4) 0.013(4) 0.001(4) 0.007(6) C8 0.048(4) 0.048(4) 0.074(5) 0.008(4) 0.005(4) 0.001(4) C10 0.051(4) 0.044(3) 0.062(4) -0.001(3) -0.002(4) -0.004(4) C11 0.059(5) 0.098(7) 0.084(6) -0.010(6) 0.001(4) -0.002(6) C12 0.104(8) 0.102(8) 0.075(6) -0.014(6) 0.039(6) 0.012(7) C13 0.125(8) 0.075(5) 0.060(5) -0.016(4) 0.003(6) 0.011(7) C14 0.099(7) 0.088(8) 0.071(5) -0.015(6) -0.013(5) -0.003(6) C15 0.055(5) 0.106(8) 0.067(5) -0.011(5) 0.002(4) -0.007(5) C20 0.056(4) 0.042(4) 0.056(4) 0.007(3) -0.001(3) -0.002(3) C21 0.071(5) 0.052(5) 0.051(4) 0.009(4) -0.003(4) 0.001(4) C22 0.094(7) 0.076(6) 0.063(5) 0.015(5) -0.002(5) -0.025(6) C23 0.066(5) 0.103(7) 0.061(5) 0.022(5) 0.007(4) -0.015(6) C24 0.068(5) 0.071(5) 0.078(5) 0.001(5) 0.018(4) -0.010(6) C25 0.072(5) 0.050(4) 0.058(4) 0.002(4) -0.003(4) -0.007(4) C30 0.062(5) 0.045(5) 0.076(5) -0.003(4) -0.029(4) 0.005(4) C31 0.054(5) 0.095(7) 0.150(8) 0.008(7) -0.041(5) -0.003(5) C32 0.090(7) 0.053(5) 0.115(8) 0.004(5) -0.020(6) 0.019(5) C33 0.103(7) 0.105(7) 0.078(5) -0.016(6) -0.045(5) 0.032(8) _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 O2 1.658(4) . ? Si1 C20 1.866(7) . ? Si1 C30 1.884(7) . ? Si1 C10 1.885(6) . ? Cl1 C1 1.762(6) . ? O1 C3 1.407(8) . ? O1 C4 1.431(7) . ? O2 C8 1.412(8) . ? O3 C2 1.414(7) . ? O3 C5 1.444(7) . ? O4 C3 1.382(7) . ? O4 C5 1.423(8) . ? O5 N1 1.178(7) . ? N1 C1 1.504(9) . ? C1 C4 1.527(9) . ? C1 C2 1.535(8) . ? C2 C3 1.543(8) . ? C4 C8 1.506(9) . ? C5 C7 1.509(9) . ? C5 C6 1.517(11) . ? C10 C11 1.367(10) . ? C10 C15 1.386(9) . ? C11 C12 1.389(11) . ? C12 C13 1.396(12) . ? C13 C14 1.356(12) . ? C14 C15 1.394(11) . ? C20 C25 1.397(9) . ? C20 C21 1.411(10) . ? C21 C22 1.362(11) . ? C22 C23 1.380(12) . ? C23 C24 1.381(12) . ? C24 C25 1.378(10) . ? C30 C31 1.529(11) . ? C30 C32 1.539(10) . ? C30 C33 1.560(10) . ? 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 O2 Si1 C20 107.7(3) . . ? O2 Si1 C30 104.5(3) . . ? C20 Si1 C30 111.6(3) . . ? O2 Si1 C10 110.5(3) . . ? C20 Si1 C10 107.4(3) . . ? C30 Si1 C10 114.9(3) . . ? C3 O1 C4 110.5(5) . . ? C8 O2 Si1 123.9(4) . . ? C2 O3 C5 108.9(5) . . ? C3 O4 C5 111.5(5) . . ? O5 N1 C1 116.2(7) . . ? N1 C1 C4 110.5(5) . . ? N1 C1 C2 111.0(5) . . ? C4 C1 C2 100.1(5) . . ? N1 C1 Cl1 113.0(5) . . ? C4 C1 Cl1 113.6(5) . . ? C2 C1 Cl1 107.8(4) . . ? O3 C2 C1 109.6(5) . . ? O3 C2 C3 103.1(5) . . ? C1 C2 C3 103.3(5) . . ? O4 C3 O1 113.2(6) . . ? O4 C3 C2 104.7(5) . . ? O1 C3 C2 106.0(5) . . ? O1 C4 C8 108.0(5) . . ? O1 C4 C1 103.9(5) . . ? C8 C4 C1 117.7(5) . . ? O4 C5 O3 105.5(5) . . ? O4 C5 C7 109.7(7) . . ? O3 C5 C7 109.7(6) . . ? O4 C5 C6 110.3(7) . . ? O3 C5 C6 107.6(6) . . ? C7 C5 C6 113.7(6) . . ? O2 C8 C4 109.6(5) . . ? C11 C10 C15 117.5(6) . . ? C11 C10 Si1 124.6(6) . . ? C15 C10 Si1 117.9(5) . . ? C10 C11 C12 121.8(8) . . ? C11 C12 C13 120.3(8) . . ? C14 C13 C12 117.9(7) . . ? C13 C14 C15 121.5(9) . . ? C10 C15 C14 120.9(8) . . ? C25 C20 C21 116.3(7) . . ? C25 C20 Si1 120.8(5) . . ? C21 C20 Si1 122.8(6) . . ? C22 C21 C20 121.0(8) . . ? C21 C22 C23 121.5(9) . . ? C24 C23 C22 119.1(8) . . ? C25 C24 C23 119.6(8) . . ? C24 C25 C20 122.4(7) . . ? C31 C30 C32 110.6(8) . . ? C31 C30 C33 108.2(7) . . ? C32 C30 C33 107.8(7) . . ? C31 C30 Si1 111.6(5) . . ? C32 C30 Si1 110.8(6) . . ? C33 C30 Si1 107.7(5) . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.199 _refine_diff_density_min -0.178 _refine_diff_density_rms 0.045 #===END data_19 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C29 H36 Cl N O5 Si' _chemical_formula_weight 542.13 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' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 10.0050(10) _cell_length_b 12.5300(10) _cell_length_c 23.255(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2915.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 38 _cell_measurement_theta_min 9.298 _cell_measurement_theta_max 18.632 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.235 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1152 _exptl_absorpt_coefficient_mu 0.209 _exptl_absorpt_correction_type 'semi-empirical \y scans (Siemens, 1994)' _exptl_absorpt_correction_T_min 0.623 _exptl_absorpt_correction_T_max 0.685 _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 '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 8.38 _diffrn_reflns_number 3664 _diffrn_reflns_av_R_equivalents 0.0248 _diffrn_reflns_av_sigmaI/netI 0.1569 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -1 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.22 _diffrn_reflns_theta_max 24.99 _reflns_number_total 3460 _reflns_number_gt 1431 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens XSCANS' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens 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^)+(0.0286P)^2^+1.8543P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.1(2) _refine_ls_number_reflns 3460 _refine_ls_number_parameters 254 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2034 _refine_ls_R_factor_gt 0.0677 _refine_ls_wR_factor_ref 0.1465 _refine_ls_wR_factor_gt 0.1042 _refine_ls_goodness_of_fit_ref 0.978 _refine_ls_restrained_S_all 0.978 _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 0.8977(3) 0.4428(2) 0.84399(11) 0.0527(7) Uani 1 1 d . . . O1 O 1.0082(6) 0.6168(6) 1.0027(3) 0.0699(19) Uani 1 1 d . . . C1 C 0.7990(9) 0.5440(7) 1.0142(4) 0.044(2) Uani 1 1 d . . . N1 N 0.7099(8) 0.4745(7) 1.0278(3) 0.059(2) Uani 1 1 d . . . Cl1 Cl 0.2582(3) 0.5641(3) 1.09217(13) 0.0995(10) Uani 1 1 d . . . O2 O 0.9074(6) 0.4881(4) 0.9101(2) 0.0567(17) Uani 1 1 d . . . C2 C 0.7755(9) 0.6622(7) 1.0072(4) 0.047(2) Uani 1 1 d . . . H2A H 0.7177 0.6769 0.9741 0.056 Uiso 1 1 calc R . . O3 O 0.7297(7) 0.7156(5) 1.0566(3) 0.0687(19) Uani 1 1 d . . . C3 C 0.9174(10) 0.7024(7) 0.9966(4) 0.054(3) Uani 1 1 d . . . H3A H 0.9250 0.7347 0.9584 0.065 Uiso 1 1 calc R . . O4 O 0.9393(6) 0.7783(4) 1.0394(3) 0.0611(18) Uani 1 1 d . . . C4 C 0.9426(8) 0.5166(7) 1.0097(4) 0.051(3) Uani 1 1 d . . . H4A H 0.9728 0.4821 1.0452 0.061 Uiso 1 1 calc R . . O5 O 0.7382(7) 0.3745(5) 1.0373(3) 0.071(2) Uani 1 1 d . . . C5 C 0.8425(10) 0.7672(8) 1.0840(5) 0.063(3) Uani 1 1 d . . . C6 C 0.8957(10) 0.6948(8) 1.1318(4) 0.092(4) Uani 1 1 d . . . H6A H 0.8295 0.6882 1.1614 0.138 Uiso 1 1 calc R . . H6B H 0.9757 0.7252 1.1476 0.138 Uiso 1 1 calc R . . H6C H 0.9153 0.6256 1.1162 0.138 Uiso 1 1 calc R . . C7 C 0.7965(10) 0.8753(7) 1.1035(4) 0.095(4) Uani 1 1 d . . . H7A H 0.7313 0.8674 1.1335 0.142 Uiso 1 1 calc R . . H7B H 0.7572 0.9127 1.0716 0.142 Uiso 1 1 calc R . . H7C H 0.8714 0.9152 1.1177 0.142 Uiso 1 1 calc R . . C8 C 0.9721(8) 0.4455(7) 0.9586(3) 0.054(2) Uani 1 1 d . . . H8A H 1.0677 0.4423 0.9520 0.065 Uiso 1 1 calc R . . H8B H 0.9401 0.3737 0.9660 0.065 Uiso 1 1 calc R . . C10 C 1.0668(8) 0.3991(6) 0.8208(3) 0.049(2) Uiso 1 1 d . . . C11 C 1.1314(9) 0.3217(7) 0.8533(4) 0.061(3) Uiso 1 1 d . . . H11A H 1.0844 0.2894 0.8831 0.073 Uiso 1 1 calc R . . C12 C 1.2623(9) 0.2898(7) 0.8436(4) 0.062(3) Uiso 1 1 d . . . H12A H 1.3029 0.2394 0.8672 0.074 Uiso 1 1 calc R . . C13 C 1.3306(10) 0.3344(7) 0.7983(4) 0.073(3) Uiso 1 1 d . . . H13A H 1.4190 0.3148 0.7919 0.088 Uiso 1 1 calc R . . C14 C 1.2705(9) 0.4081(7) 0.7620(4) 0.069(3) Uiso 1 1 d . . . H14A H 1.3160 0.4363 0.7307 0.082 Uiso 1 1 calc R . . C15 C 1.1384(8) 0.4385(7) 0.7744(4) 0.061(3) Uiso 1 1 d . . . H15A H 1.0969 0.4875 0.7503 0.074 Uiso 1 1 calc R . . C20 C 0.7831(8) 0.3259(6) 0.8414(4) 0.048(2) Uiso 1 1 d . . . C21 C 0.6955(9) 0.3031(7) 0.8869(4) 0.063(3) Uiso 1 1 d . . . H21A H 0.6998 0.3442 0.9201 0.075 Uiso 1 1 calc R . . C22 C 0.6009(9) 0.2193(7) 0.8837(4) 0.068(3) Uiso 1 1 d . . . H22A H 0.5441 0.2050 0.9144 0.082 Uiso 1 1 calc R . . C23 C 0.5949(10) 0.1603(7) 0.8345(4) 0.072(3) Uiso 1 1 d . . . H23A H 0.5322 0.1057 0.8318 0.087 Uiso 1 1 calc R . . C24 C 0.6779(9) 0.1789(8) 0.7896(4) 0.073(3) Uiso 1 1 d . . . H24A H 0.6715 0.1372 0.7566 0.087 Uiso 1 1 calc R . . C25 C 0.7730(9) 0.2602(7) 0.7926(4) 0.065(3) Uiso 1 1 d . . . H25A H 0.8307 0.2711 0.7618 0.077 Uiso 1 1 calc R . . C30 C 0.8227(8) 0.5576(8) 0.8037(4) 0.057(3) Uiso 1 1 d . . . C31 C 0.6843(9) 0.5862(8) 0.8293(4) 0.092(4) Uiso 1 1 d . . . H31A H 0.6270 0.5248 0.8278 0.138 Uiso 1 1 calc R . . H31B H 0.6453 0.6433 0.8075 0.138 Uiso 1 1 calc R . . H31C H 0.6950 0.6083 0.8686 0.138 Uiso 1 1 calc R . . C32 C 0.7965(9) 0.5278(7) 0.7395(4) 0.085(4) Uiso 1 1 d . . . H32A H 0.7409 0.4654 0.7377 0.128 Uiso 1 1 calc R . . H32B H 0.8800 0.5135 0.7207 0.128 Uiso 1 1 calc R . . H32C H 0.7524 0.5861 0.7206 0.128 Uiso 1 1 calc R . . C33 C 0.9116(10) 0.6564(7) 0.8068(4) 0.091(3) Uiso 1 1 d . . . H33A H 0.9980 0.6401 0.7912 0.136 Uiso 1 1 calc R . . H33B H 0.9211 0.6782 0.8462 0.136 Uiso 1 1 calc R . . H33C H 0.8716 0.7132 0.7851 0.136 Uiso 1 1 calc R . . C50 C 0.5648(8) 0.5026(7) 1.0324(4) 0.049(3) Uani 1 1 d . . . H50A H 0.5498 0.5750 1.0178 0.059 Uiso 1 1 calc R . . C51 C 0.4737(11) 0.4265(9) 1.0032(4) 0.077(3) Uani 1 1 d . . . H51A H 0.4884 0.3998 0.9665 0.093 Uiso 1 1 calc R . . C52 C 0.3726(11) 0.4017(8) 1.0342(5) 0.079(3) Uani 1 1 d . . . H52A H 0.3049 0.3556 1.0226 0.095 Uiso 1 1 calc R . . C53 C 0.3773(9) 0.4561(9) 1.0917(4) 0.076(3) Uani 1 1 d . . . H53A H 0.3584 0.4054 1.1227 0.091 Uiso 1 1 calc R . . C54 C 0.5207(9) 0.4954(8) 1.0951(4) 0.071(3) Uani 1 1 d . . . H54A H 0.5761 0.4455 1.1163 0.085 Uiso 1 1 calc R . . H54B H 0.5252 0.5647 1.1136 0.085 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 0.0597(16) 0.0474(15) 0.0510(15) 0.0024(15) 0.0002(16) 0.0104(17) O1 0.041(4) 0.067(4) 0.102(5) -0.015(5) -0.005(4) -0.008(4) C1 0.045(6) 0.048(6) 0.038(5) 0.004(5) 0.002(5) -0.008(6) N1 0.054(6) 0.061(6) 0.063(6) 0.005(5) 0.002(5) 0.013(5) Cl1 0.0659(18) 0.120(2) 0.113(2) 0.012(2) 0.0126(18) 0.004(2) O2 0.067(4) 0.056(4) 0.047(3) -0.001(3) -0.007(4) 0.012(4) C2 0.036(6) 0.049(6) 0.056(6) 0.006(6) -0.006(5) -0.011(5) O3 0.059(5) 0.069(5) 0.078(5) -0.017(4) 0.013(4) 0.007(4) C3 0.069(7) 0.050(6) 0.044(6) 0.007(5) -0.011(6) -0.020(6) O4 0.066(5) 0.049(4) 0.068(4) -0.011(4) 0.011(4) -0.015(4) C4 0.036(6) 0.052(6) 0.066(6) 0.002(6) 0.000(5) 0.000(5) O5 0.073(5) 0.053(4) 0.087(5) 0.024(4) 0.015(4) 0.007(4) C5 0.047(7) 0.074(8) 0.067(7) -0.019(7) 0.003(7) -0.014(6) C6 0.105(9) 0.111(9) 0.062(6) -0.004(7) -0.008(7) -0.015(9) C7 0.100(9) 0.075(7) 0.108(9) -0.028(7) 0.015(8) 0.005(8) C8 0.059(6) 0.042(5) 0.062(6) -0.005(6) 0.005(6) 0.005(6) C50 0.048(6) 0.049(6) 0.051(6) 0.028(5) 0.003(5) 0.002(5) C51 0.060(7) 0.104(10) 0.069(7) 0.013(8) -0.003(7) -0.003(8) C52 0.071(8) 0.078(8) 0.088(9) -0.009(7) -0.006(7) -0.028(7) C53 0.058(7) 0.096(8) 0.073(7) 0.030(7) 0.014(6) -0.007(8) C54 0.053(6) 0.105(9) 0.055(6) 0.014(7) 0.000(6) -0.009(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 O2 1.642(5) . ? Si1 C10 1.857(8) . ? Si1 C20 1.861(8) . ? Si1 C30 1.874(9) . ? O1 C3 1.412(10) . ? O1 C4 1.427(9) . ? C1 N1 1.285(9) . ? C1 C4 1.481(11) . ? C1 C2 1.509(11) . ? N1 O5 1.304(8) . ? N1 C50 1.497(11) . ? Cl1 C53 1.803(10) . ? O2 C8 1.406(8) . ? C2 O3 1.405(9) . ? C2 C3 1.527(11) . ? O3 C5 1.449(10) . ? C3 O4 1.394(9) . ? O4 C5 1.425(10) . ? C4 C8 1.513(10) . ? C5 C7 1.501(12) . ? C5 C6 1.529(12) . ? C10 C15 1.386(10) . ? C10 C11 1.389(10) . ? C11 C12 1.388(11) . ? C12 C13 1.373(11) . ? C13 C14 1.388(10) . ? C14 C15 1.406(11) . ? C20 C21 1.404(11) . ? C20 C25 1.405(10) . ? C21 C22 1.415(11) . ? C22 C23 1.363(10) . ? C23 C24 1.354(11) . ? C24 C25 1.396(11) . ? C30 C33 1.527(11) . ? C30 C31 1.549(11) . ? C30 C32 1.561(11) . ? C50 C51 1.483(12) . ? C50 C54 1.527(10) . ? C51 C52 1.280(11) . ? C52 C53 1.500(13) . ? C53 C54 1.519(11) . ? 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 O2 Si1 C10 108.7(3) . . ? O2 Si1 C20 109.8(4) . . ? C10 Si1 C20 108.7(4) . . ? O2 Si1 C30 103.0(3) . . ? C10 Si1 C30 116.5(4) . . ? C20 Si1 C30 109.9(4) . . ? C3 O1 C4 112.5(6) . . ? N1 C1 C4 122.2(8) . . ? N1 C1 C2 125.7(8) . . ? C4 C1 C2 111.8(8) . . ? C1 N1 O5 122.8(8) . . ? C1 N1 C50 122.1(8) . . ? O5 N1 C50 115.1(8) . . ? C8 O2 Si1 130.3(5) . . ? O3 C2 C1 115.5(8) . . ? O3 C2 C3 106.2(7) . . ? C1 C2 C3 101.3(8) . . ? C2 O3 C5 108.6(7) . . ? O4 C3 O1 110.2(7) . . ? O4 C3 C2 104.8(8) . . ? O1 C3 C2 109.4(7) . . ? C3 O4 C5 110.3(7) . . ? O1 C4 C1 104.5(7) . . ? O1 C4 C8 109.8(7) . . ? C1 C4 C8 112.4(8) . . ? O4 C5 O3 104.6(7) . . ? O4 C5 C7 109.9(9) . . ? O3 C5 C7 107.3(8) . . ? O4 C5 C6 110.5(8) . . ? O3 C5 C6 109.0(8) . . ? C7 C5 C6 115.1(9) . . ? O2 C8 C4 108.5(7) . . ? C15 C10 C11 115.6(8) . . ? C15 C10 Si1 126.3(7) . . ? C11 C10 Si1 118.1(6) . . ? C12 C11 C10 123.5(9) . . ? C13 C12 C11 118.5(10) . . ? C12 C13 C14 121.4(10) . . ? C13 C14 C15 117.6(9) . . ? C10 C15 C14 123.3(9) . . ? C21 C20 C25 116.4(8) . . ? C21 C20 Si1 121.4(7) . . ? C25 C20 Si1 122.1(7) . . ? C20 C21 C22 122.0(9) . . ? C23 C22 C21 118.4(9) . . ? C24 C23 C22 121.7(10) . . ? C23 C24 C25 120.3(9) . . ? C24 C25 C20 121.1(9) . . ? C33 C30 C31 108.4(8) . . ? C33 C30 C32 109.7(8) . . ? C31 C30 C32 105.8(7) . . ? C33 C30 Si1 111.5(6) . . ? C31 C30 Si1 110.1(6) . . ? C32 C30 Si1 111.2(7) . . ? C51 C50 N1 114.3(8) . . ? C51 C50 C54 102.8(7) . . ? N1 C50 C54 109.6(7) . . ? C52 C51 C50 112.6(9) . . ? C51 C52 C53 111.5(10) . . ? C52 C53 C54 102.9(8) . . ? C52 C53 Cl1 109.1(7) . . ? C54 C53 Cl1 112.4(8) . . ? C53 C54 C50 104.0(8) . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.259 _refine_diff_density_min -0.228 _refine_diff_density_rms 0.054 #===END