# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2004 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Prof Nakcheol Jeong' _publ_contact_author_address ; Department of Chemistry Korea University Seoul 136-701 KOREA ; _publ_contact_author_email NJEONG@KOREA.AC.KR _publ_section_title ; Desymmetrization of meso-Dienyne by Asymmetric Pauson-Khand Type Reaction Catalysts. ; loop_ _publ_author_name 'Nakcheol Jeong' 'Jun Hun Choi' 'Dong Hoon Kim' data_2a _database_code_depnum_ccdc_archive 'CCDC 230163' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H19 N O3 S' _chemical_formula_weight 317.39 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 '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 5.794(8) _cell_length_b 14.0776(12) _cell_length_c 19.4686(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1588(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 2.30 _cell_measurement_theta_max 22.5 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.327 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 672 _exptl_absorpt_coefficient_mu 0.216 _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 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 'Enraf Nonius CAD4' _diffrn_measurement_method 'omega-2theta scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time '2 hr' _diffrn_standards_decay_% none _diffrn_reflns_number 1064 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0325 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 26.17 _reflns_number_total 1064 _reflns_number_gt 1002 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0855P)^2^+0.0474P] 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 1064 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0516 _refine_ls_R_factor_gt 0.0490 _refine_ls_wR_factor_ref 0.1298 _refine_ls_wR_factor_gt 0.1274 _refine_ls_goodness_of_fit_ref 1.121 _refine_ls_restrained_S_all 1.121 _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 S1 S 0.9838(3) 1.70941(12) 1.21296(9) 0.0766(6) Uani 1 1 d . . . N1 N 1.1133(7) 1.7185(4) 1.2861(2) 0.0652(13) Uani 1 1 d . . . O1 O 1.7916(9) 1.8310(4) 1.4614(2) 0.1092(19) Uani 1 1 d . . . O2 O 0.9752(9) 1.6118(3) 1.1960(2) 0.1011(17) Uani 1 1 d . . . O3 O 0.7804(7) 1.7628(4) 1.2210(3) 0.1003(16) Uani 1 1 d . . . C1 C 1.3191(9) 1.6630(4) 1.3029(3) 0.0614(16) Uani 1 1 d . . . H1 H 1.4463 1.6816 1.2726 0.074 Uiso 1 1 calc R . . C2 C 1.3617(10) 1.7017(5) 1.3748(3) 0.0650(16) Uani 1 1 d . . . H2 H 1.2508 1.6733 1.4068 0.078 Uiso 1 1 calc R . . C3 C 1.3115(9) 1.8041(5) 1.3669(3) 0.0616(15) Uani 1 1 d . . . C4 C 1.1275(11) 1.8155(4) 1.3158(3) 0.0729(18) Uani 1 1 d . . . H4A H 1.1689 1.8620 1.2812 0.088 Uiso 1 1 calc R . . H4B H 0.9830 1.8339 1.3371 0.088 Uiso 1 1 calc R . . C5 C 1.2872(14) 1.5584(5) 1.3000(3) 0.083(2) Uani 1 1 d . . . H5 H 1.1445 1.5336 1.3126 0.100 Uiso 1 1 calc R . . C6 C 1.4473(16) 1.4996(5) 1.2808(4) 0.104(2) Uani 1 1 d . . . H6A H 1.5915 1.5224 1.2679 0.125 Uiso 1 1 calc R . . H6B H 1.4177 1.4346 1.2800 0.125 Uiso 1 1 calc R . . C7 C 1.5962(11) 1.7003(5) 1.4059(3) 0.0765(19) Uani 1 1 d . . . H7A H 1.7118 1.6811 1.3727 0.092 Uiso 1 1 calc R . . H7B H 1.6023 1.6577 1.4451 0.092 Uiso 1 1 calc R . . C8 C 1.6304(13) 1.8022(6) 1.4277(3) 0.081(2) Uani 1 1 d . . . C9 C 1.4564(13) 1.8621(5) 1.3982(3) 0.0729(19) Uani 1 1 d . . . C10 C 1.4678(17) 1.9674(5) 1.3988(4) 0.108(3) Uani 1 1 d . . . H10A H 1.5981 1.9874 1.4256 0.130 Uiso 1 1 calc R . . H10B H 1.3288 1.9925 1.4186 0.130 Uiso 1 1 calc R . . H10C H 1.4838 1.9904 1.3526 0.130 Uiso 1 1 calc R . . C11 C 1.1435(9) 1.7692(4) 1.1513(3) 0.0558(14) Uani 1 1 d . . . C12 C 1.3394(10) 1.7285(4) 1.1261(4) 0.0689(16) Uani 1 1 d . . . H12 H 1.3865 1.6687 1.1407 0.083 Uiso 1 1 calc R . . C13 C 1.4648(10) 1.7781(5) 1.0786(3) 0.0740(18) Uani 1 1 d . . . H13 H 1.5976 1.7503 1.0608 0.089 Uiso 1 1 calc R . . C14 C 1.4045(12) 1.8660(5) 1.0562(3) 0.0678(18) Uani 1 1 d . . . C15 C 1.2089(11) 1.9049(5) 1.0820(3) 0.0724(18) Uani 1 1 d . . . H15 H 1.1620 1.9649 1.0678 0.087 Uiso 1 1 calc R . . C16 C 1.0820(11) 1.8563(4) 1.1285(3) 0.0710(17) Uani 1 1 d . . . H16 H 0.9476 1.8838 1.1454 0.085 Uiso 1 1 calc R . . C17 C 1.5517(12) 1.9200(6) 1.0067(3) 0.098(2) Uani 1 1 d . . . H17A H 1.6882 1.8840 0.9966 0.118 Uiso 1 1 calc R . . H17B H 1.5945 1.9799 1.0265 0.118 Uiso 1 1 calc R . . H17C H 1.4668 1.9309 0.9650 0.118 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 S1 0.0506(8) 0.0958(13) 0.0834(11) 0.0141(10) -0.0130(8) -0.0295(10) N1 0.046(2) 0.078(3) 0.072(3) 0.013(3) 0.001(2) -0.015(2) O1 0.087(4) 0.159(5) 0.082(3) -0.009(3) -0.025(3) -0.034(4) O2 0.101(4) 0.089(3) 0.113(4) 0.009(3) -0.034(4) -0.051(3) O3 0.036(2) 0.147(4) 0.118(4) 0.028(4) -0.007(3) -0.016(3) C1 0.041(3) 0.081(4) 0.062(4) 0.014(3) -0.001(3) -0.014(3) C2 0.050(3) 0.091(5) 0.054(3) 0.015(3) 0.008(3) -0.015(3) C3 0.045(3) 0.085(4) 0.055(3) 0.004(3) 0.008(3) -0.004(3) C4 0.053(3) 0.096(5) 0.070(4) 0.002(4) 0.011(3) -0.002(3) C5 0.082(5) 0.074(5) 0.094(5) 0.016(4) 0.003(4) -0.023(4) C6 0.109(7) 0.087(4) 0.117(6) -0.002(5) -0.004(6) -0.007(5) C7 0.061(3) 0.107(5) 0.061(4) 0.016(4) -0.007(3) -0.007(4) C8 0.071(4) 0.123(6) 0.050(3) -0.001(4) -0.005(3) -0.024(5) C9 0.077(5) 0.093(5) 0.048(3) -0.004(3) 0.001(3) -0.013(4) C10 0.120(7) 0.112(6) 0.094(5) -0.048(4) -0.002(5) -0.017(6) C11 0.045(3) 0.064(4) 0.058(3) -0.003(3) -0.010(3) -0.009(3) C12 0.063(4) 0.067(4) 0.076(4) -0.007(3) -0.007(4) 0.005(3) C13 0.053(3) 0.103(5) 0.066(4) -0.017(4) 0.005(3) 0.009(4) C14 0.064(4) 0.082(5) 0.057(4) -0.002(3) 0.002(3) -0.008(4) C15 0.071(4) 0.063(4) 0.083(4) 0.009(3) 0.014(4) 0.009(4) C16 0.055(3) 0.077(4) 0.081(4) 0.010(4) 0.012(3) 0.007(3) C17 0.080(5) 0.132(6) 0.082(4) 0.014(4) 0.019(4) -0.013(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 S1 O3 1.406(5) . ? S1 O2 1.415(4) . ? S1 N1 1.615(5) . ? S1 C11 1.735(6) . ? N1 C1 1.462(7) . ? N1 C4 1.485(8) . ? O1 C8 1.212(8) . ? C1 C5 1.486(9) . ? C1 C2 1.521(9) . ? C2 C3 1.479(9) . ? C2 C7 1.489(9) . ? C3 C9 1.320(8) . ? C3 C4 1.467(8) . ? C5 C6 1.298(10) . ? C7 C8 1.509(10) . ? C8 C9 1.435(10) . ? C9 C10 1.483(9) . ? C11 C16 1.351(8) . ? C11 C12 1.363(8) . ? C12 C13 1.366(8) . ? C13 C14 1.358(8) . ? C14 C15 1.355(9) . ? C14 C17 1.496(8) . ? C15 C16 1.352(8) . ? 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 O3 S1 O2 121.0(3) . . ? O3 S1 N1 104.4(3) . . ? O2 S1 N1 107.4(3) . . ? O3 S1 C11 105.3(3) . . ? O2 S1 C11 109.2(3) . . ? N1 S1 C11 108.9(3) . . ? C1 N1 C4 111.0(5) . . ? C1 N1 S1 122.3(4) . . ? C4 N1 S1 116.2(4) . . ? N1 C1 C5 114.8(5) . . ? N1 C1 C2 98.5(5) . . ? C5 C1 C2 114.2(5) . . ? C3 C2 C7 103.6(6) . . ? C3 C2 C1 102.8(5) . . ? C7 C2 C1 121.2(6) . . ? C9 C3 C4 135.0(6) . . ? C9 C3 C2 115.5(6) . . ? C4 C3 C2 108.6(5) . . ? C3 C4 N1 101.8(5) . . ? C6 C5 C1 123.6(7) . . ? C2 C7 C8 102.8(7) . . ? O1 C8 C9 124.2(8) . . ? O1 C8 C7 124.8(8) . . ? C9 C8 C7 110.8(6) . . ? C3 C9 C8 105.5(6) . . ? C3 C9 C10 130.6(7) . . ? C8 C9 C10 123.5(7) . . ? C16 C11 C12 118.9(6) . . ? C16 C11 S1 121.8(5) . . ? C12 C11 S1 119.3(5) . . ? C11 C12 C13 118.1(6) . . ? C14 C13 C12 123.1(6) . . ? C15 C14 C13 117.7(6) . . ? C15 C14 C17 120.7(7) . . ? C13 C14 C17 121.6(7) . . ? C16 C15 C14 119.9(6) . . ? C11 C16 C15 122.4(6) . . ? _diffrn_measured_fraction_theta_max 0.571 _diffrn_reflns_theta_full 26.17 _diffrn_measured_fraction_theta_full 0.571 _refine_diff_density_max 0.156 _refine_diff_density_min -0.216 _refine_diff_density_rms 0.040 data_6a _database_code_depnum_ccdc_archive 'CCDC 230164' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H35 N3 O3 S' _chemical_formula_weight 433.60 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 11.130(2) _cell_length_b 7.964(2) _cell_length_c 13.859(2) _cell_angle_alpha 90.00 _cell_angle_beta 106.16(2) _cell_angle_gamma 90.00 _cell_volume 1179.9(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 3.00 _cell_measurement_theta_max 22.2 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.220 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 468 _exptl_absorpt_coefficient_mu 0.165 _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 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 'Enraf Nonius CAD4' _diffrn_measurement_method 'omega-2 theta scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time '2 hr' _diffrn_standards_decay_% none _diffrn_reflns_number 1318 _diffrn_reflns_av_R_equivalents 0.0392 _diffrn_reflns_av_sigmaI/netI 0.0460 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.53 _diffrn_reflns_theta_max 25.48 _reflns_number_total 1252 _reflns_number_gt 1172 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0346P)^2^+0.4285P] 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 1252 _refine_ls_number_parameters 271 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0524 _refine_ls_R_factor_gt 0.0482 _refine_ls_wR_factor_ref 0.1024 _refine_ls_wR_factor_gt 0.0995 _refine_ls_goodness_of_fit_ref 1.128 _refine_ls_restrained_S_all 1.127 _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 S1 S 0.5474(2) 0.2775(3) 0.30162(17) 0.0770(7) Uani 1 1 d . . . O1 O 0.4146(6) 0.2684(10) 0.2817(5) 0.111(2) Uani 1 1 d . . . O2 O 0.6251(7) 0.1407(7) 0.3496(5) 0.109(2) Uani 1 1 d . . . O3 O 1.0126(5) 1.2168(8) 0.1909(4) 0.0862(18) Uani 1 1 d . . . N1 N 0.5937(6) 0.4435(7) 0.3690(4) 0.0562(16) Uani 1 1 d . . . N2 N 0.9118(5) 0.8376(7) 0.2928(4) 0.0596(17) Uani 1 1 d . . . N3 N 0.8877(5) 0.8893(7) 0.1924(4) 0.0522(15) Uani 1 1 d . . . C1 C 0.5244(6) 0.6035(8) 0.3450(5) 0.0519(18) Uani 1 1 d . . . H1 H 0.4802 0.6066 0.2732 0.062 Uiso 1 1 calc R . . C2 C 0.6289(6) 0.7317(8) 0.3676(5) 0.0530(19) Uani 1 1 d . . . H2 H 0.6019 0.8352 0.3937 0.064 Uiso 1 1 calc R . . C3 C 0.7363(7) 0.6532(10) 0.4458(5) 0.062(2) Uani 1 1 d . . . H3 H 0.7247 0.6616 0.5132 0.074 Uiso 1 1 calc R . . C4 C 0.7290(7) 0.4721(10) 0.4098(5) 0.064(2) Uani 1 1 d . . . H4A H 0.7719 0.4579 0.3582 0.076 Uiso 1 1 calc R . . H4B H 0.7651 0.3961 0.4649 0.076 Uiso 1 1 calc R . . C5 C 0.4303(7) 0.6233(11) 0.4061(5) 0.074(2) Uani 1 1 d . . . H5A H 0.3867 0.5177 0.4058 0.089 Uiso 1 1 calc R . . H5B H 0.4749 0.6492 0.4752 0.089 Uiso 1 1 calc R . . C6 C 0.3364(8) 0.7589(16) 0.3659(7) 0.114(4) Uani 1 1 d . . . H6A H 0.2797 0.7670 0.4067 0.136 Uiso 1 1 calc R . . H6B H 0.2904 0.7325 0.2981 0.136 Uiso 1 1 calc R . . H6C H 0.3789 0.8641 0.3670 0.136 Uiso 1 1 calc R . . C7 C 0.6834(6) 0.7717(11) 0.2797(5) 0.0562(18) Uani 1 1 d . . . H7A H 0.6658 0.6816 0.2307 0.067 Uiso 1 1 calc R . . H7B H 0.6486 0.8753 0.2468 0.067 Uiso 1 1 calc R . . C8 C 0.8228(7) 0.7890(10) 0.3271(5) 0.0571(18) Uani 1 1 d . . . C9 C 0.8523(7) 0.7462(10) 0.4389(5) 0.065(2) Uani 1 1 d . . . H9 H 0.8554 0.8522 0.4754 0.078 Uiso 1 1 calc R . . C10 C 0.9767(7) 0.6592(13) 0.4814(6) 0.093(3) Uani 1 1 d . . . H10A H 1.0429 0.7300 0.4731 0.112 Uiso 1 1 calc R . . H10B H 0.9773 0.5552 0.4465 0.112 Uiso 1 1 calc R . . H10C H 0.9888 0.6371 0.5516 0.112 Uiso 1 1 calc R . . C11 C 0.8171(7) 0.7768(12) 0.1138(5) 0.072(2) Uani 1 1 d . . . H11A H 0.7279 0.7865 0.1053 0.087 Uiso 1 1 calc R . . H11B H 0.8424 0.6609 0.1286 0.087 Uiso 1 1 calc R . . C12 C 0.8514(7) 0.8386(14) 0.0224(6) 0.092(3) Uani 1 1 d . . . H12A H 0.8607 0.7445 -0.0194 0.111 Uiso 1 1 calc R . . H12B H 0.7863 0.9118 -0.0169 0.111 Uiso 1 1 calc R . . C13 C 0.9709(7) 0.9316(12) 0.0569(5) 0.074(2) Uani 1 1 d . . . H13A H 0.9597 1.0477 0.0351 0.089 Uiso 1 1 calc R . . H13B H 1.0341 0.8809 0.0301 0.089 Uiso 1 1 calc R . . C14 C 1.0093(6) 0.9212(10) 0.1705(6) 0.062(2) Uani 1 1 d . . . H14 H 1.0625 0.8221 0.1907 0.074 Uiso 1 1 calc R . . C15 C 1.0762(6) 1.0686(10) 0.2248(6) 0.064(2) Uani 1 1 d . . . H15A H 1.0853 1.0560 0.2961 0.076 Uiso 1 1 calc R . . H15B H 1.1593 1.0741 0.2154 0.076 Uiso 1 1 calc R . . C16 C 1.0751(9) 1.3612(13) 0.2415(8) 0.114(4) Uani 1 1 d . . . H16A H 1.0291 1.4602 0.2140 0.136 Uiso 1 1 calc R . . H16B H 1.1577 1.3672 0.2330 0.136 Uiso 1 1 calc R . . H16C H 1.0808 1.3534 0.3118 0.136 Uiso 1 1 calc R . . C17 C 0.5793(7) 0.3136(9) 0.1856(5) 0.058(2) Uani 1 1 d . . . C18 C 0.6915(6) 0.2647(10) 0.1710(5) 0.0606(19) Uani 1 1 d . . . H18 H 0.7504 0.2086 0.2215 0.073 Uiso 1 1 calc R . . C19 C 0.7158(6) 0.2992(11) 0.0812(6) 0.065(2) Uani 1 1 d . . . H19 H 0.7918 0.2657 0.0717 0.078 Uiso 1 1 calc R . . C20 C 0.6300(7) 0.3827(10) 0.0041(6) 0.0580(19) Uani 1 1 d . . . C21 C 0.5184(7) 0.4315(10) 0.0202(6) 0.066(2) Uani 1 1 d . . . H21 H 0.4599 0.4889 -0.0300 0.079 Uiso 1 1 calc R . . C22 C 0.4925(7) 0.3967(10) 0.1089(6) 0.067(2) Uani 1 1 d . . . H22 H 0.4161 0.4289 0.1180 0.080 Uiso 1 1 calc R . . C23 C 0.6568(7) 0.4158(13) -0.0939(6) 0.086(3) Uani 1 1 d . . . H23A H 0.5872 0.4737 -0.1379 0.104 Uiso 1 1 calc R . . H23B H 0.6698 0.3112 -0.1239 0.104 Uiso 1 1 calc R . . H23C H 0.7306 0.4838 -0.0828 0.104 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 S1 0.1044(18) 0.0471(12) 0.0978(16) -0.0143(14) 0.0583(14) -0.0216(14) O1 0.112(5) 0.116(5) 0.132(5) -0.052(5) 0.077(4) -0.064(5) O2 0.200(7) 0.031(3) 0.124(5) 0.015(3) 0.091(5) 0.011(4) O3 0.075(4) 0.064(4) 0.110(5) -0.002(4) 0.011(4) -0.001(3) N1 0.068(4) 0.038(4) 0.067(4) 0.001(3) 0.027(3) -0.002(3) N2 0.062(4) 0.049(4) 0.062(4) 0.007(3) 0.007(3) -0.008(3) N3 0.044(3) 0.057(4) 0.052(4) 0.008(3) 0.008(3) 0.002(3) C1 0.055(4) 0.053(5) 0.054(4) -0.001(4) 0.026(4) 0.003(4) C2 0.067(5) 0.041(5) 0.051(4) -0.003(3) 0.016(4) 0.000(4) C3 0.080(6) 0.059(5) 0.045(4) 0.001(4) 0.017(4) -0.007(5) C4 0.073(6) 0.050(5) 0.069(5) 0.017(4) 0.023(4) 0.005(4) C5 0.077(5) 0.089(7) 0.062(5) 0.005(5) 0.031(4) 0.011(5) C6 0.101(7) 0.152(10) 0.093(6) -0.002(8) 0.038(6) 0.046(8) C7 0.064(5) 0.044(4) 0.059(4) 0.006(4) 0.014(4) 0.007(4) C8 0.066(5) 0.045(4) 0.055(4) -0.001(4) 0.009(4) -0.007(4) C9 0.074(5) 0.060(6) 0.054(5) -0.005(4) 0.007(4) -0.018(5) C10 0.069(6) 0.121(8) 0.084(7) 0.018(6) 0.011(5) -0.008(6) C11 0.070(5) 0.066(5) 0.074(5) -0.001(5) 0.006(4) -0.009(5) C12 0.067(6) 0.134(10) 0.080(6) -0.021(6) 0.027(5) -0.018(6) C13 0.071(5) 0.084(6) 0.075(6) -0.009(5) 0.033(4) 0.000(5) C14 0.043(4) 0.056(5) 0.087(6) 0.008(5) 0.019(4) 0.007(4) C15 0.051(5) 0.064(6) 0.077(5) 0.016(5) 0.019(4) 0.003(5) C16 0.130(9) 0.071(7) 0.131(9) -0.002(7) 0.022(7) 0.004(7) C17 0.064(5) 0.049(5) 0.067(5) -0.012(4) 0.026(4) -0.001(4) C18 0.069(5) 0.046(4) 0.065(5) 0.002(4) 0.015(4) 0.011(4) C19 0.048(4) 0.071(5) 0.079(5) 0.005(5) 0.025(4) 0.008(4) C20 0.047(4) 0.063(5) 0.059(5) -0.012(4) 0.006(4) -0.010(4) C21 0.054(5) 0.067(6) 0.067(6) -0.009(5) 0.002(4) 0.004(4) C22 0.050(5) 0.070(6) 0.080(6) -0.022(5) 0.018(4) -0.003(4) C23 0.080(6) 0.103(8) 0.070(6) -0.008(5) 0.012(5) -0.009(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 S1 O1 1.429(6) . ? S1 O2 1.434(7) . ? S1 N1 1.618(6) . ? S1 C17 1.764(7) . ? O3 C15 1.390(9) . ? O3 C16 1.424(10) . ? N1 C4 1.471(8) . ? N1 C1 1.479(9) . ? N2 C8 1.272(8) . ? N2 N3 1.404(7) . ? N3 C11 1.460(9) . ? N3 C14 1.488(8) . ? C1 C2 1.514(9) . ? C1 C5 1.527(9) . ? C2 C3 1.508(9) . ? C2 C7 1.538(8) . ? C3 C9 1.514(9) . ? C3 C4 1.521(11) . ? C5 C6 1.498(11) . ? C7 C8 1.513(9) . ? C8 C9 1.531(9) . ? C9 C10 1.513(10) . ? C11 C12 1.504(10) . ? C12 C13 1.480(10) . ? C13 C14 1.514(10) . ? C14 C15 1.479(10) . ? C17 C18 1.376(9) . ? C17 C22 1.388(10) . ? C18 C19 1.373(9) . ? C19 C20 1.388(10) . ? C20 C21 1.377(10) . ? C20 C23 1.493(10) . ? C21 C22 1.367(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 O1 S1 O2 120.6(5) . . ? O1 S1 N1 107.4(4) . . ? O2 S1 N1 107.4(3) . . ? O1 S1 C17 107.0(4) . . ? O2 S1 C17 107.4(4) . . ? N1 S1 C17 106.3(3) . . ? C15 O3 C16 112.7(6) . . ? C4 N1 C1 111.5(5) . . ? C4 N1 S1 118.4(5) . . ? C1 N1 S1 120.8(5) . . ? C8 N2 N3 120.4(6) . . ? N2 N3 C11 118.3(6) . . ? N2 N3 C14 108.6(5) . . ? C11 N3 C14 106.5(6) . . ? N1 C1 C2 102.2(5) . . ? N1 C1 C5 111.1(6) . . ? C2 C1 C5 115.0(6) . . ? C3 C2 C1 106.2(6) . . ? C3 C2 C7 104.3(5) . . ? C1 C2 C7 115.2(5) . . ? C2 C3 C9 105.7(6) . . ? C2 C3 C4 101.4(6) . . ? C9 C3 C4 114.3(7) . . ? N1 C4 C3 103.2(6) . . ? C6 C5 C1 112.5(6) . . ? C8 C7 C2 105.0(5) . . ? N2 C8 C7 132.6(6) . . ? N2 C8 C9 118.4(6) . . ? C7 C8 C9 108.9(6) . . ? C10 C9 C3 117.1(7) . . ? C10 C9 C8 114.3(6) . . ? C3 C9 C8 103.1(6) . . ? N3 C11 C12 102.6(6) . . ? C13 C12 C11 107.9(6) . . ? C12 C13 C14 106.1(6) . . ? C15 C14 N3 112.9(6) . . ? C15 C14 C13 116.3(7) . . ? N3 C14 C13 102.2(5) . . ? O3 C15 C14 111.4(6) . . ? C18 C17 C22 119.3(7) . . ? C18 C17 S1 120.6(6) . . ? C22 C17 S1 120.1(6) . . ? C19 C18 C17 119.5(7) . . ? C18 C19 C20 121.7(7) . . ? C21 C20 C19 118.0(7) . . ? C21 C20 C23 121.0(7) . . ? C19 C20 C23 121.0(7) . . ? C22 C21 C20 120.9(7) . . ? C21 C22 C17 120.6(7) . . ? _diffrn_measured_fraction_theta_max 0.528 _diffrn_reflns_theta_full 25.48 _diffrn_measured_fraction_theta_full 0.528 _refine_diff_density_max 0.127 _refine_diff_density_min -0.153 _refine_diff_density_rms 0.032