data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'J. Snaith' 'Claire A. M. Cariou' _publ_contact_author_name 'J. Snaith' _publ_contact_author_address ; School of Chemical Sciences The University of Birmingham Edgbaston Birmingham B15 2TT UNITED KINGDOM ; _publ_contact_author_email J.S.SNAITH@BHAM.AC.UK _publ_requested_journal 'Organic & Biomolecular Chemistry' _publ_section_title ; Stereoselective synthesis of 2,4,5-trisubstituted piperidines by carbonyl ene and Prins cyclisations ; # Attachment 'clc76b.cif.txt' data_clc76b _database_code_depnum_ccdc_archive 'CCDC 288320' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H23 N O3 S' _chemical_formula_weight 309.41 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c 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' '-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 22.4722(3) _cell_length_b 7.87270(10) _cell_length_c 19.9610(2) _cell_angle_alpha 90.00 _cell_angle_beta 112.1780(10) _cell_angle_gamma 90.00 _cell_volume 3270.17(7) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.257 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1328 _exptl_absorpt_coefficient_mu 1.837 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.5270 _exptl_absorpt_correction_T_max 0.8978 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10104 _diffrn_reflns_av_R_equivalents 0.0250 _diffrn_reflns_av_sigmaI/netI 0.0200 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 4.25 _diffrn_reflns_theta_max 70.45 _reflns_number_total 2943 _reflns_number_gt 2689 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.0599P)^2^+2.1762P] 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_number_reflns 2943 _refine_ls_number_parameters 194 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0423 _refine_ls_R_factor_gt 0.0392 _refine_ls_wR_factor_ref 0.1150 _refine_ls_wR_factor_gt 0.1123 _refine_ls_goodness_of_fit_ref 1.090 _refine_ls_restrained_S_all 1.090 _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 C1 C 0.12497(9) 0.3532(2) 0.50386(10) 0.0460(4) Uani 1 1 d . . . H1 H 0.0815 0.3949 0.4764 0.055 Uiso 1 1 calc R . . C2 C 0.13897(10) 0.3694(2) 0.58402(10) 0.0482(4) Uani 1 1 d . . . H2A H 0.1353 0.4879 0.5954 0.058 Uiso 1 1 calc R . . H2B H 0.1829 0.3339 0.6111 0.058 Uiso 1 1 calc R . . C3 C 0.09390(9) 0.2641(2) 0.60814(10) 0.0430(4) Uani 1 1 d . . . H3 H 0.1122 0.2606 0.6611 0.052 Uiso 1 1 calc R . . C4 C 0.08128(9) 0.0647(2) 0.50558(9) 0.0437(4) Uani 1 1 d . . . H4A H 0.0381 0.0999 0.4755 0.052 Uiso 1 1 calc R . . H4B H 0.0855 -0.0547 0.4962 0.052 Uiso 1 1 calc R . . C5 C 0.12959(8) 0.1673(2) 0.48479(9) 0.0410(4) Uani 1 1 d . . . H5 H 0.1728 0.1269 0.5145 0.049 Uiso 1 1 calc R . . C6 C 0.12039(9) 0.1446(3) 0.40611(10) 0.0505(5) Uani 1 1 d . . . C7 C 0.17028(12) 0.1248(4) 0.38759(12) 0.0691(6) Uani 1 1 d . . . H7A H 0.1643 0.1152 0.3390 0.083 Uiso 1 1 calc R . . H7B H 0.2115 0.1204 0.4231 0.083 Uiso 1 1 calc R . . C8 C 0.05361(12) 0.1521(4) 0.35008(12) 0.0807(8) Uani 1 1 d . . . H8A H 0.0554 0.1577 0.3029 0.121 Uiso 1 1 calc R . . H8B H 0.0322 0.2511 0.3579 0.121 Uiso 1 1 calc R . . H8C H 0.0304 0.0522 0.3535 0.121 Uiso 1 1 calc R . . C9 C 0.02663(11) 0.3379(3) 0.58542(14) 0.0632(6) Uani 1 1 d . . . H9A H 0.0064 0.3373 0.5336 0.095 Uiso 1 1 calc R . . H9B H 0.0292 0.4524 0.6028 0.095 Uiso 1 1 calc R . . H9C H 0.0018 0.2705 0.6055 0.095 Uiso 1 1 calc R . . C10 C 0.20343(9) -0.0809(2) 0.65721(10) 0.0433(4) Uani 1 1 d . . . C11 C 0.24656(10) 0.0139(3) 0.71323(11) 0.0551(5) Uani 1 1 d . . . H11 H 0.2320 0.0825 0.7418 0.066 Uiso 1 1 calc R . . C12 C 0.31128(11) 0.0051(3) 0.72603(12) 0.0650(6) Uani 1 1 d . . . H12 H 0.3401 0.0691 0.7634 0.078 Uiso 1 1 calc R . . C13 C 0.33421(11) -0.0964(3) 0.68473(14) 0.0658(6) Uani 1 1 d . . . C14 C 0.29043(12) -0.1895(3) 0.62910(14) 0.0660(6) Uani 1 1 d . . . H14 H 0.3051 -0.2581 0.6007 0.079 Uiso 1 1 calc R . . C15 C 0.22521(10) -0.1830(3) 0.61484(12) 0.0541(5) Uani 1 1 d . . . H15 H 0.1964 -0.2464 0.5772 0.065 Uiso 1 1 calc R . . C16 C 0.40558(13) -0.1104(5) 0.70066(19) 0.1015(11) Uani 1 1 d . . . H16A H 0.4211 -0.2183 0.7227 0.152 Uiso 1 1 calc R . . H16B H 0.4280 -0.0208 0.7330 0.152 Uiso 1 1 calc R . . H16C H 0.4128 -0.1009 0.6564 0.152 Uiso 1 1 calc R . . N1 N 0.09063(7) 0.08645(18) 0.58190(8) 0.0408(3) Uani 1 1 d . . . O1 O 0.17029(9) 0.4582(2) 0.48898(9) 0.0680(4) Uani 1 1 d . . . H1A H 0.1738 0.4261 0.4516 0.102 Uiso 1 1 calc R . . O2 O 0.11313(7) -0.0197(2) 0.70447(7) 0.0591(4) Uani 1 1 d . . . O3 O 0.09161(7) -0.22059(17) 0.60299(8) 0.0590(4) Uani 1 1 d . . . S1 S 0.12025(2) -0.06673(5) 0.63883(2) 0.04278(16) 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 C1 0.0456(10) 0.0437(9) 0.0482(10) 0.0067(8) 0.0172(8) -0.0014(8) C2 0.0561(11) 0.0393(9) 0.0504(10) -0.0051(8) 0.0214(9) -0.0056(8) C3 0.0477(10) 0.0382(9) 0.0434(9) -0.0018(7) 0.0176(8) 0.0022(8) C4 0.0470(10) 0.0435(9) 0.0382(9) -0.0020(7) 0.0134(8) -0.0046(8) C5 0.0360(8) 0.0481(9) 0.0366(8) 0.0025(7) 0.0110(7) 0.0016(7) C6 0.0498(10) 0.0597(11) 0.0408(9) 0.0015(9) 0.0157(8) -0.0001(9) C7 0.0661(14) 0.0975(18) 0.0498(11) -0.0052(12) 0.0288(11) 0.0022(13) C8 0.0612(14) 0.132(2) 0.0397(10) -0.0004(13) 0.0085(10) -0.0058(15) C9 0.0597(13) 0.0592(12) 0.0763(14) 0.0009(11) 0.0322(11) 0.0129(10) C10 0.0465(10) 0.0398(9) 0.0435(9) 0.0098(7) 0.0167(8) 0.0054(8) C11 0.0532(11) 0.0581(12) 0.0481(10) 0.0011(9) 0.0126(9) 0.0045(10) C12 0.0523(12) 0.0732(15) 0.0573(12) 0.0098(11) 0.0071(10) -0.0024(11) C13 0.0505(12) 0.0785(15) 0.0709(14) 0.0315(13) 0.0257(11) 0.0103(11) C14 0.0731(15) 0.0635(13) 0.0775(15) 0.0157(12) 0.0469(13) 0.0174(12) C15 0.0608(12) 0.0471(10) 0.0591(11) 0.0025(9) 0.0280(10) 0.0027(9) C16 0.0555(15) 0.146(3) 0.109(2) 0.045(2) 0.0379(15) 0.0185(17) N1 0.0471(8) 0.0372(7) 0.0371(7) 0.0016(6) 0.0149(6) 0.0006(6) O1 0.0812(11) 0.0632(9) 0.0662(10) 0.0028(8) 0.0353(9) -0.0238(8) O2 0.0643(9) 0.0744(10) 0.0467(7) 0.0156(7) 0.0301(7) 0.0105(8) O3 0.0589(8) 0.0390(7) 0.0776(10) 0.0067(7) 0.0240(8) -0.0061(6) S1 0.0456(3) 0.0400(3) 0.0450(3) 0.00875(17) 0.0197(2) 0.00175(17) _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 C1 O1 1.427(2) . ? C1 C2 1.515(3) . ? C1 C5 1.525(3) . ? C2 C3 1.521(3) . ? C3 N1 1.486(2) . ? C3 C9 1.520(3) . ? C4 N1 1.467(2) . ? C4 C5 1.531(2) . ? C5 C6 1.515(2) . ? C6 C7 1.316(3) . ? C6 C8 1.496(3) . ? C10 C15 1.383(3) . ? C10 C11 1.389(3) . ? C10 S1 1.7672(19) . ? C11 C12 1.380(3) . ? C12 C13 1.380(4) . ? C13 C14 1.383(4) . ? C13 C16 1.517(3) . ? C14 C15 1.385(3) . ? N1 S1 1.6179(15) . ? O2 S1 1.4275(14) . ? O3 S1 1.4302(15) . ? 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 C1 C2 106.91(15) . . ? O1 C1 C5 112.48(16) . . ? C2 C1 C5 109.76(15) . . ? C1 C2 C3 112.99(15) . . ? N1 C3 C9 110.07(16) . . ? N1 C3 C2 110.61(14) . . ? C9 C3 C2 113.79(17) . . ? N1 C4 C5 112.43(14) . . ? C6 C5 C1 112.11(15) . . ? C6 C5 C4 112.66(15) . . ? C1 C5 C4 108.47(14) . . ? C7 C6 C8 121.0(2) . . ? C7 C6 C5 120.52(18) . . ? C8 C6 C5 118.42(17) . . ? C15 C10 C11 120.27(19) . . ? C15 C10 S1 120.02(16) . . ? C11 C10 S1 119.70(15) . . ? C12 C11 C10 119.2(2) . . ? C13 C12 C11 121.6(2) . . ? C12 C13 C14 118.3(2) . . ? C12 C13 C16 121.4(3) . . ? C14 C13 C16 120.4(3) . . ? C13 C14 C15 121.5(2) . . ? C10 C15 C14 119.2(2) . . ? C4 N1 C3 116.40(14) . . ? C4 N1 S1 120.12(12) . . ? C3 N1 S1 120.11(12) . . ? O2 S1 O3 119.58(9) . . ? O2 S1 N1 107.00(8) . . ? O3 S1 N1 106.96(8) . . ? O2 S1 C10 107.58(9) . . ? O3 S1 C10 106.95(9) . . ? N1 S1 C10 108.38(8) . . ? _diffrn_measured_fraction_theta_max 0.937 _diffrn_reflns_theta_full 70.45 _diffrn_measured_fraction_theta_full 0.937 _refine_diff_density_max 0.338 _refine_diff_density_min -0.300 _refine_diff_density_rms 0.040 # Attachment 'clc115b.cif.txt' data_clc115b _database_code_depnum_ccdc_archive 'CCDC 288321' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H27 N O3 S' _chemical_formula_sum 'C18 H27 N O3 S' _chemical_formula_weight 337.47 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.47570(10) _cell_length_b 19.2080(3) _cell_length_c 11.8021(2) _cell_angle_alpha 90.00 _cell_angle_beta 97.9640(10) _cell_angle_gamma 90.00 _cell_volume 1902.87(5) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 5423 _cell_measurement_theta_min 4.43 _cell_measurement_theta_max 70.59 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.178 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 728 _exptl_absorpt_coefficient_mu 1.617 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.4987 _exptl_absorpt_correction_T_max 0.6427 _exptl_absorpt_process_details 'Sadabs in SaintPlus' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart 6000 CCD' _diffrn_measurement_method 'CCD slices' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12353 _diffrn_reflns_av_R_equivalents 0.0338 _diffrn_reflns_av_sigmaI/netI 0.0495 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 4.43 _diffrn_reflns_theta_max 70.59 _reflns_number_total 5917 _reflns_number_gt 5423 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.0584P)^2^+0.0814P] 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 0.009(13) _refine_ls_number_reflns 5917 _refine_ls_number_parameters 425 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0413 _refine_ls_R_factor_gt 0.0374 _refine_ls_wR_factor_ref 0.1035 _refine_ls_wR_factor_gt 0.0998 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _refine_ls_shift/su_max 0.046 _refine_ls_shift/su_mean 0.001 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 C20 C -0.1354(8) -0.7914(2) -0.9483(6) 0.151(2) Uani 1 1 d . . . H20A H -0.0469 -0.8027 -0.8914 0.226 Uiso 1 1 calc R . . H20B H -0.1235 -0.8148 -1.0185 0.226 Uiso 1 1 calc R . . H20C H -0.2327 -0.8061 -0.9225 0.226 Uiso 1 1 calc R . . C21 C -0.1403(5) -0.71303(18) -0.9682(4) 0.0930(10) Uani 1 1 d . . . C22 C -0.2139(4) -0.6841(2) -1.0678(3) 0.0927(10) Uani 1 1 d . . . H22 H -0.2632 -0.7130 -1.1253 0.111 Uiso 1 1 calc R . . C23 C -0.2166(4) -0.61294(18) -1.0847(2) 0.0770(8) Uani 1 1 d . . . H23 H -0.2652 -0.5946 -1.1537 0.092 Uiso 1 1 calc R . . C24 C -0.1472(3) -0.56884(14) -0.9992(2) 0.0607(6) Uani 1 1 d . . . C25 C -0.0747(3) -0.59720(17) -0.8981(2) 0.0731(7) Uani 1 1 d . . . H25 H -0.0282 -0.5684 -0.8395 0.088 Uiso 1 1 calc R . . C26 C -0.0713(4) -0.66848(18) -0.8841(3) 0.0852(9) Uani 1 1 d . . . H26 H -0.0209 -0.6871 -0.8157 0.102 Uiso 1 1 calc R . . N2 N -0.3210(2) -0.44962(11) -0.97899(16) 0.0545(4) Uani 1 1 d . . . C28 C -0.4709(2) -0.45861(14) -1.0561(2) 0.0575(5) Uani 1 1 d . . . H28A H -0.4477 -0.4653 -1.1336 0.069 Uiso 1 1 calc R . . H28B H -0.5344 -0.4166 -1.0550 0.069 Uiso 1 1 calc R . . C29 C -0.5657(3) -0.51979(14) -1.0228(2) 0.0592(6) Uani 1 1 d . . . H29 H -0.4964 -0.5607 -1.0217 0.071 Uiso 1 1 calc R . . C30 C -0.6002(3) -0.50898(15) -0.8998(2) 0.0653(6) Uani 1 1 d . . . H30 H -0.6545 -0.5502 -0.8753 0.078 Uiso 1 1 calc R . . C31 C -0.4455(3) -0.49831(15) -0.8207(2) 0.0667(6) Uani 1 1 d . . . H31A H -0.3868 -0.5418 -0.8153 0.080 Uiso 1 1 calc R . . H31B H -0.4706 -0.4876 -0.7449 0.080 Uiso 1 1 calc R . . C32 C -0.3373(3) -0.44115(14) -0.8560(2) 0.0566(5) Uani 1 1 d . . . H32 H -0.2315 -0.4485 -0.8124 0.068 Uiso 1 1 calc R . . C33 C -0.3866(4) -0.36616(17) -0.8333(3) 0.0840(9) Uani 1 1 d . . . H33 H -0.4934 -0.3579 -0.8746 0.101 Uiso 1 1 calc R . . C34 C -0.3904(6) -0.3543(3) -0.7062(4) 0.1360(18) Uani 1 1 d . . . H34A H -0.2912 -0.3691 -0.6637 0.204 Uiso 1 1 calc R . . H34B H -0.4761 -0.3807 -0.6821 0.204 Uiso 1 1 calc R . . H34C H -0.4064 -0.3058 -0.6925 0.204 Uiso 1 1 calc R . . C35 C -0.2709(6) -0.31405(19) -0.8754(4) 0.1172(15) Uani 1 1 d . . . H35A H -0.1648 -0.3233 -0.8385 0.176 Uiso 1 1 calc R . . H35B H -0.3011 -0.2676 -0.8575 0.176 Uiso 1 1 calc R . . H35C H -0.2742 -0.3186 -0.9567 0.176 Uiso 1 1 calc R . . C36 C -0.7140(3) -0.53542(19) -1.1070(3) 0.0761(8) Uani 1 1 d . . . C37 C -0.7643(5) -0.6094(2) -1.1117(4) 0.1227(16) Uani 1 1 d . . . H37A H -0.8669 -0.6135 -1.1572 0.184 Uiso 1 1 calc R . . H37B H -0.7705 -0.6259 -1.0357 0.184 Uiso 1 1 calc R . . H37C H -0.6880 -0.6367 -1.1453 0.184 Uiso 1 1 calc R . . O3 O -0.0301(2) -0.44896(12) -0.9403(2) 0.0809(5) Uani 1 1 d . . . O4 O -0.1677(2) -0.46520(13) -1.13800(18) 0.0863(6) Uani 1 1 d . . . O6 O -0.69732(19) -0.44942(12) -0.89121(17) 0.0779(5) Uani 1 1 d . . . H6 H -0.7889 -0.4580 -0.9200 0.117 Uiso 1 1 calc R . . S2 S -0.15759(6) -0.47791(3) -1.01841(6) 0.06225(16) Uani 1 1 d . . . C1 C -0.8492(5) -0.4855(2) -0.6182(4) 0.1074(11) Uani 1 1 d . . . H1A H -0.8458 -0.5125 -0.5495 0.161 Uiso 1 1 calc R . . H1B H -0.7506 -0.4909 -0.6487 0.161 Uiso 1 1 calc R . . H1C H -0.9356 -0.5013 -0.6735 0.161 Uiso 1 1 calc R . . C2 C -0.8734(3) -0.40997(16) -0.5915(3) 0.0739(7) Uani 1 1 d . . . C3 C -0.8708(4) -0.36008(18) -0.6736(3) 0.0795(8) Uani 1 1 d . . . H3 H -0.8543 -0.3733 -0.7468 0.095 Uiso 1 1 calc R . . C4 C -0.8918(3) -0.29092(17) -0.6506(2) 0.0711(7) Uani 1 1 d . . . H4 H -0.8891 -0.2579 -0.7080 0.085 Uiso 1 1 calc R . . C5 C -0.9170(3) -0.27015(14) -0.5426(2) 0.0593(6) Uani 1 1 d . . . C6 C -0.9219(3) -0.31946(15) -0.4583(2) 0.0695(7) Uani 1 1 d . . . H6' H -0.9398 -0.3062 -0.3854 0.083 Uiso 1 1 calc R . . C7 C -0.8998(4) -0.38895(17) -0.4835(3) 0.0803(8) Uani 1 1 d . . . H7 H -0.9028 -0.4222 -0.4266 0.096 Uiso 1 1 calc R . . N1 N -0.7525(2) -0.15125(11) -0.47605(17) 0.0553(4) Uani 1 1 d . . . C9 C -0.6587(3) -0.12327(14) -0.5625(2) 0.0623(6) Uani 1 1 d . . . H9 H -0.7294 -0.1216 -0.6355 0.075 Uiso 1 1 calc R . . C10 C -0.5244(4) -0.1736(2) -0.5771(3) 0.0823(8) Uani 1 1 d . . . H10A H -0.5698 -0.2143 -0.6180 0.099 Uiso 1 1 calc R . . H10B H -0.4539 -0.1515 -0.6243 0.099 Uiso 1 1 calc R . . C11 C -0.4264(3) -0.19729(15) -0.4667(3) 0.0763(8) Uani 1 1 d . . . H11 H -0.3512 -0.2332 -0.4842 0.092 Uiso 1 1 calc R . . C12 C -0.5350(3) -0.22783(14) -0.3859(3) 0.0692(7) Uani 1 1 d . . . H12 H -0.5902 -0.2677 -0.4252 0.083 Uiso 1 1 calc R . . C13 C -0.6614(2) -0.17454(14) -0.36768(19) 0.0554(5) Uani 1 1 d . . . H13A H -0.7339 -0.1948 -0.3200 0.066 Uiso 1 1 calc R . . H13B H -0.6106 -0.1346 -0.3276 0.066 Uiso 1 1 calc R . . C14 C -0.6079(4) -0.04776(16) -0.5308(3) 0.0732(7) Uani 1 1 d . . . H14 H -0.5446 -0.0480 -0.4548 0.088 Uiso 1 1 calc R . . C15 C -0.7515(5) -0.0025(2) -0.5268(5) 0.1181(14) Uani 1 1 d . . . H15A H -0.8241 -0.0082 -0.5962 0.177 Uiso 1 1 calc R . . H15B H -0.7190 0.0453 -0.5189 0.177 Uiso 1 1 calc R . . H15C H -0.8033 -0.0158 -0.4627 0.177 Uiso 1 1 calc R . . C16 C -0.5042(6) -0.0186(3) -0.6170(3) 0.1168(15) Uani 1 1 d . . . H16A H -0.5602 -0.0229 -0.6931 0.175 Uiso 1 1 calc R . . H16B H -0.4062 -0.0443 -0.6112 0.175 Uiso 1 1 calc R . . H16C H -0.4814 0.0296 -0.6004 0.175 Uiso 1 1 calc R . . C17 C -0.4446(4) -0.25488(17) -0.2748(4) 0.0989(12) Uani 1 1 d . . . C18 C -0.4451(10) -0.2231(4) -0.1757(5) 0.208(4) Uani 1 1 d . . . H18A H -0.3757 -0.2375 -0.1120 0.249 Uiso 1 1 calc R . . H18B H -0.5149 -0.1864 -0.1696 0.249 Uiso 1 1 calc R . . C19 C -0.3341(8) -0.3132(3) -0.2849(7) 0.183(3) Uani 1 1 d . . . H19A H -0.2966 -0.3110 -0.3580 0.275 Uiso 1 1 calc R . . H19B H -0.3886 -0.3565 -0.2782 0.275 Uiso 1 1 calc R . . H19C H -0.2452 -0.3099 -0.2252 0.275 Uiso 1 1 calc R . . C38 C -0.7940(3) -0.4876(3) -1.1711(3) 0.0969(11) Uani 1 1 d . . . H38A H -0.8845 -0.4999 -1.2209 0.116 Uiso 1 1 calc R . . H38B H -0.7600 -0.4416 -1.1666 0.116 Uiso 1 1 calc R . . O1 O -0.9976(2) -0.14608(13) -0.6131(2) 0.0896(7) Uani 1 1 d . . . O2 O -1.00991(18) -0.17620(12) -0.41172(18) 0.0793(5) Uani 1 1 d . . . O5 O -0.3392(2) -0.14040(12) -0.4115(2) 0.0855(6) Uani 1 1 d . . . H5 H -0.2435 -0.1472 -0.4107 0.128 Uiso 1 1 calc R . . S1 S -0.93123(6) -0.18080(3) -0.51150(5) 0.06291(16) 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 C20 0.178(5) 0.078(3) 0.206(6) -0.004(3) 0.061(5) 0.015(3) C21 0.093(2) 0.079(2) 0.113(3) -0.0150(19) 0.0339(19) 0.0147(17) C22 0.089(2) 0.089(3) 0.099(2) -0.036(2) 0.0091(16) 0.0126(18) C23 0.0714(16) 0.092(2) 0.0654(16) -0.0191(14) 0.0028(12) 0.0168(14) C24 0.0434(11) 0.0787(17) 0.0607(13) -0.0120(11) 0.0095(9) 0.0114(10) C25 0.0647(15) 0.085(2) 0.0667(16) -0.0126(13) 0.0008(12) 0.0138(13) C26 0.092(2) 0.085(2) 0.0800(18) 0.0091(16) 0.0156(15) 0.0238(17) N2 0.0379(8) 0.0623(11) 0.0628(11) -0.0007(9) 0.0058(7) -0.0001(7) C28 0.0423(11) 0.0724(16) 0.0577(12) -0.0024(10) 0.0064(8) 0.0043(9) C29 0.0425(11) 0.0671(16) 0.0697(14) -0.0130(11) 0.0137(9) 0.0019(10) C30 0.0467(12) 0.0808(17) 0.0708(15) -0.0017(12) 0.0164(10) -0.0059(11) C31 0.0569(13) 0.0842(19) 0.0600(14) 0.0080(12) 0.0109(10) 0.0058(11) C32 0.0435(10) 0.0658(14) 0.0583(13) -0.0066(10) -0.0008(9) 0.0096(10) C33 0.0710(17) 0.0734(19) 0.100(2) -0.0268(16) -0.0139(14) 0.0210(14) C34 0.144(4) 0.138(4) 0.128(3) -0.067(3) 0.024(3) 0.023(3) C35 0.140(4) 0.0589(19) 0.140(3) -0.005(2) -0.029(3) -0.007(2) C36 0.0468(13) 0.107(2) 0.0779(17) -0.0342(16) 0.0193(11) -0.0122(14) C37 0.093(3) 0.126(4) 0.150(4) -0.058(3) 0.020(2) -0.041(2) O3 0.0411(8) 0.0860(13) 0.1156(15) -0.0119(11) 0.0109(9) -0.0072(8) O4 0.0611(10) 0.1202(18) 0.0839(13) 0.0227(12) 0.0320(9) 0.0118(10) O6 0.0425(8) 0.1117(15) 0.0796(12) -0.0332(10) 0.0094(8) 0.0083(9) S2 0.0389(3) 0.0740(4) 0.0754(4) 0.0019(3) 0.0134(2) 0.0017(2) C1 0.103(2) 0.088(3) 0.130(3) -0.025(2) 0.010(2) 0.000(2) C2 0.0575(14) 0.0794(19) 0.0822(19) -0.0152(15) 0.0004(12) -0.0047(12) C3 0.0777(18) 0.090(2) 0.0709(17) -0.0192(15) 0.0127(13) -0.0087(15) C4 0.0732(16) 0.0801(19) 0.0593(14) -0.0011(12) 0.0070(11) -0.0084(13) C5 0.0400(11) 0.0792(17) 0.0570(13) -0.0061(11) 0.0010(8) -0.0044(10) C6 0.0754(16) 0.0771(18) 0.0580(14) -0.0052(12) 0.0165(11) -0.0125(13) C7 0.0825(18) 0.080(2) 0.0774(18) 0.0050(14) 0.0065(13) -0.0131(15) N1 0.0416(9) 0.0655(12) 0.0581(11) 0.0010(8) 0.0045(7) 0.0031(8) C9 0.0623(14) 0.0762(17) 0.0481(12) -0.0032(11) 0.0068(10) -0.0032(11) C10 0.0713(16) 0.099(2) 0.0827(18) -0.0266(17) 0.0317(14) -0.0049(16) C11 0.0474(12) 0.0661(17) 0.117(2) -0.0254(15) 0.0194(13) 0.0105(11) C12 0.0480(12) 0.0528(14) 0.102(2) -0.0097(13) -0.0062(12) 0.0004(10) C13 0.0421(10) 0.0648(14) 0.0585(12) 0.0043(11) 0.0049(8) 0.0020(10) C14 0.0747(16) 0.0723(18) 0.0705(16) 0.0104(12) 0.0028(12) -0.0076(13) C15 0.102(3) 0.077(2) 0.171(4) 0.007(2) 0.003(3) 0.015(2) C16 0.124(3) 0.134(4) 0.089(2) 0.036(2) 0.004(2) -0.044(3) C17 0.0674(17) 0.0665(19) 0.150(3) 0.026(2) -0.0316(18) -0.0019(14) C18 0.287(9) 0.176(6) 0.124(4) -0.001(4) -0.096(5) 0.098(6) C19 0.153(5) 0.115(4) 0.266(8) 0.042(4) -0.029(5) 0.060(4) C38 0.0517(14) 0.147(3) 0.088(2) -0.024(2) -0.0054(13) 0.0024(18) O1 0.0667(12) 0.0914(15) 0.1002(15) 0.0089(11) -0.0257(10) 0.0112(10) O2 0.0423(8) 0.0971(14) 0.1013(13) -0.0185(12) 0.0203(8) 0.0063(9) O5 0.0420(9) 0.0759(13) 0.1391(19) -0.0208(12) 0.0143(10) -0.0015(8) S1 0.0389(2) 0.0749(4) 0.0725(4) -0.0038(3) -0.0011(2) 0.0072(2) _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 C20 C21 1.524(6) . ? C21 C22 1.370(5) . ? C21 C26 1.378(5) . ? C22 C23 1.380(5) . ? C23 C24 1.385(4) . ? C24 C25 1.376(4) . ? C24 S2 1.762(3) . ? C25 C26 1.379(5) . ? N2 C28 1.467(3) . ? N2 C32 1.486(3) . ? N2 S2 1.6148(18) . ? C28 C29 1.506(4) . ? C29 C36 1.521(4) . ? C29 C30 1.534(4) . ? C30 O6 1.421(3) . ? C30 C31 1.515(4) . ? C31 C32 1.525(4) . ? C32 C33 1.533(4) . ? C33 C34 1.522(6) . ? C33 C35 1.532(6) . ? C36 C38 1.316(5) . ? C36 C37 1.483(5) . ? O3 S2 1.432(2) . ? O4 S2 1.423(2) . ? C1 C2 1.504(5) . ? C2 C3 1.365(5) . ? C2 C7 1.385(4) . ? C3 C4 1.372(5) . ? C4 C5 1.380(4) . ? C5 C6 1.378(4) . ? C5 S1 1.763(3) . ? C6 C7 1.386(4) . ? N1 C13 1.469(3) . ? N1 C9 1.479(3) . ? N1 S1 1.6176(19) . ? C9 C10 1.521(4) . ? C9 C14 1.544(4) . ? C10 C11 1.515(5) . ? C11 O5 1.425(3) . ? C11 C12 1.531(4) . ? C12 C17 1.516(5) . ? C12 C13 1.519(3) . ? C14 C15 1.501(5) . ? C14 C16 1.539(5) . ? C17 C18 1.320(7) . ? C17 C19 1.475(7) . ? O1 S1 1.418(2) . ? O2 S1 1.4342(19) . ? 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 C22 C21 C26 117.6(3) . . ? C22 C21 C20 122.2(4) . . ? C26 C21 C20 120.2(4) . . ? C21 C22 C23 121.5(3) . . ? C22 C23 C24 120.2(3) . . ? C25 C24 C23 118.9(3) . . ? C25 C24 S2 120.8(2) . . ? C23 C24 S2 120.3(2) . . ? C24 C25 C26 119.8(3) . . ? C21 C26 C25 122.0(3) . . ? C28 N2 C32 115.39(16) . . ? C28 N2 S2 119.04(15) . . ? C32 N2 S2 121.19(14) . . ? N2 C28 C29 112.2(2) . . ? C28 C29 C36 113.9(2) . . ? C28 C29 C30 108.7(2) . . ? C36 C29 C30 113.35(18) . . ? O6 C30 C31 107.9(2) . . ? O6 C30 C29 111.4(2) . . ? C31 C30 C29 109.83(18) . . ? C30 C31 C32 115.5(2) . . ? N2 C32 C31 109.21(19) . . ? N2 C32 C33 109.7(2) . . ? C31 C32 C33 116.1(2) . . ? C34 C33 C35 108.9(3) . . ? C34 C33 C32 110.8(3) . . ? C35 C33 C32 110.8(3) . . ? C38 C36 C37 121.6(3) . . ? C38 C36 C29 123.5(3) . . ? C37 C36 C29 114.9(3) . . ? O4 S2 O3 120.55(13) . . ? O4 S2 N2 106.97(11) . . ? O3 S2 N2 106.53(11) . . ? O4 S2 C24 107.03(13) . . ? O3 S2 C24 106.39(12) . . ? N2 S2 C24 109.02(11) . . ? C3 C2 C7 118.0(3) . . ? C3 C2 C1 120.8(3) . . ? C7 C2 C1 121.2(3) . . ? C2 C3 C4 121.6(3) . . ? C3 C4 C5 120.2(3) . . ? C6 C5 C4 119.5(3) . . ? C6 C5 S1 120.61(19) . . ? C4 C5 S1 119.8(2) . . ? C5 C6 C7 119.2(3) . . ? C2 C7 C6 121.5(3) . . ? C13 N1 C9 116.30(17) . . ? C13 N1 S1 118.61(16) . . ? C9 N1 S1 121.53(16) . . ? N1 C9 C10 109.3(2) . . ? N1 C9 C14 109.5(2) . . ? C10 C9 C14 115.9(2) . . ? C11 C10 C9 115.0(2) . . ? O5 C11 C10 110.5(3) . . ? O5 C11 C12 109.1(2) . . ? C10 C11 C12 110.2(2) . . ? C17 C12 C13 113.0(3) . . ? C17 C12 C11 113.2(2) . . ? C13 C12 C11 109.1(2) . . ? N1 C13 C12 112.2(2) . . ? C15 C14 C16 110.5(3) . . ? C15 C14 C9 110.5(3) . . ? C16 C14 C9 110.4(3) . . ? C18 C17 C19 120.2(4) . . ? C18 C17 C12 123.0(3) . . ? C19 C17 C12 116.1(5) . . ? O1 S1 O2 119.33(14) . . ? O1 S1 N1 107.55(13) . . ? O2 S1 N1 106.94(11) . . ? O1 S1 C5 108.21(13) . . ? O2 S1 C5 106.49(13) . . ? N1 S1 C5 107.86(10) . . ? _diffrn_measured_fraction_theta_max 0.956 _diffrn_reflns_theta_full 70.59 _diffrn_measured_fraction_theta_full 0.956 _refine_diff_density_max 0.462 _refine_diff_density_min -0.197 _refine_diff_density_rms 0.037