# Electronic Supplementary Material (ESI) for Chemical Science # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'Chemical Science' _journal_coden_cambridge 1475 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email tooi@apchem.nagoya-u.ac.jp _publ_contact_author_name 'Ooi, Takashi' _publ_author_name 'Takashi Ooi' data_4 _database_code_depnum_ccdc_archive 'CCDC 884839' #TrackingRef '- 4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H15 N O3 S' _chemical_formula_weight 289.34 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 5.4774(13) _cell_length_b 10.390(2) _cell_length_c 25.084(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1427.5(6) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 6483 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 28.40 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.346 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 608 _exptl_absorpt_coefficient_mu 0.233 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.845 _exptl_absorpt_correction_T_max 0.966 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.366 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10282 _diffrn_reflns_av_R_equivalents 0.0315 _diffrn_reflns_av_sigmaI/netI 0.0331 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 28.40 _reflns_number_total 3559 _reflns_number_gt 3432 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0497P)^2^+0.3522P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _chemical_absolute_configuration ad _refine_ls_hydrogen_treatment constr _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 -0.03(7) _refine_ls_number_reflns 3559 _refine_ls_number_parameters 182 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0408 _refine_ls_R_factor_gt 0.0392 _refine_ls_wR_factor_ref 0.0972 _refine_ls_wR_factor_gt 0.0961 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.071 _refine_ls_shift/su_max 0.011 _refine_ls_shift/su_mean 0.002 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 0.36404(8) 0.44046(4) 0.158049(17) 0.02942(11) Uani 1 1 d . . . C6 C 0.1441(3) 0.60106(15) 0.08897(6) 0.0233(3) Uani 1 1 d . . . C7 C 0.1434(3) 0.46003(15) 0.10367(6) 0.0254(3) Uani 1 1 d . . . H7 H -0.0227 0.4358 0.1168 0.030 Uiso 1 1 calc R . . C9 C 0.3288(3) 0.27487(15) 0.17374(6) 0.0250(3) Uani 1 1 d . . . C10 C 0.1336(3) 0.23277(17) 0.20465(7) 0.0320(4) Uani 1 1 d . . . H10 H 0.0125 0.2923 0.2159 0.038 Uiso 1 1 calc R . . C1 C 0.3325(3) 0.65605(16) 0.05933(7) 0.0274(3) Uani 1 1 d . . . H1 H 0.4629 0.6038 0.0469 0.033 Uiso 1 1 calc R . . C3 C 0.1416(4) 0.86378(16) 0.06579(7) 0.0315(4) Uani 1 1 d . . . H3 H 0.1410 0.9534 0.0582 0.038 Uiso 1 1 calc R . . O3 O 0.2613(3) -0.10607(13) 0.21944(6) 0.0399(3) Uani 1 1 d . . . C14 C 0.5028(3) 0.18744(16) 0.15730(8) 0.0295(3) Uani 1 1 d . . . H14 H 0.6351 0.2158 0.1358 0.035 Uiso 1 1 calc R . . C12 C 0.2927(3) 0.01723(16) 0.20282(7) 0.0289(4) Uani 1 1 d . . . C13 C 0.4875(3) 0.05835(18) 0.17169(7) 0.0317(4) Uani 1 1 d . . . H13 H 0.6088 -0.0010 0.1604 0.038 Uiso 1 1 calc R . . N1 N 0.0378(4) 0.38679(15) 0.01271(7) 0.0369(4) Uani 1 1 d . . . O2 O -0.1779(3) 0.37577(19) 0.02148(8) 0.0600(5) Uani 1 1 d . . . C11 C 0.1151(4) 0.10493(18) 0.21897(8) 0.0341(4) Uani 1 1 d . . . H11 H -0.0192 0.0766 0.2399 0.041 Uiso 1 1 calc R . . C2 C 0.3305(3) 0.78704(17) 0.04792(7) 0.0294(4) Uani 1 1 d . . . H2A H 0.4596 0.8239 0.0277 0.035 Uiso 1 1 calc R . . C5 C -0.0453(3) 0.67911(18) 0.10651(8) 0.0313(4) Uani 1 1 d . . . H5 H -0.1750 0.6429 0.1267 0.038 Uiso 1 1 calc R . . O1 O 0.1200(4) 0.41074(18) -0.03066(6) 0.0623(5) Uani 1 1 d . . . C8 C 0.2141(3) 0.37087(16) 0.05820(7) 0.0303(4) Uani 1 1 d . . . H8A H 0.3816 0.3913 0.0460 0.036 Uiso 1 1 calc R . . H8B H 0.2120 0.2805 0.0707 0.036 Uiso 1 1 calc R . . C15 C 0.4262(4) -0.20099(17) 0.19964(8) 0.0388(5) Uani 1 1 d . . . H15A H 0.4088 -0.2077 0.1609 0.058 Uiso 1 1 calc R . . H15B H 0.3889 -0.2843 0.2160 0.058 Uiso 1 1 calc R . . H15C H 0.5940 -0.1762 0.2084 0.058 Uiso 1 1 calc R . . C4 C -0.0466(4) 0.80935(18) 0.09479(9) 0.0357(4) Uani 1 1 d . . . H4 H -0.1777 0.8617 0.1068 0.043 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 0.0397(2) 0.02181(18) 0.02678(19) 0.00048(15) -0.00860(17) -0.00338(16) C6 0.0262(7) 0.0226(7) 0.0213(7) -0.0015(5) -0.0031(6) -0.0004(6) C7 0.0289(7) 0.0231(7) 0.0242(7) -0.0011(5) -0.0039(6) -0.0005(7) C9 0.0320(8) 0.0208(7) 0.0224(7) 0.0018(5) -0.0046(6) -0.0024(6) C10 0.0273(8) 0.0313(8) 0.0373(9) -0.0009(7) 0.0025(7) 0.0062(8) C1 0.0265(8) 0.0291(8) 0.0268(8) -0.0007(6) 0.0024(6) 0.0021(7) C3 0.0379(9) 0.0222(7) 0.0343(9) 0.0013(6) -0.0062(8) -0.0014(7) O3 0.0544(9) 0.0243(6) 0.0410(8) 0.0049(5) 0.0107(7) -0.0033(6) C14 0.0320(8) 0.0282(8) 0.0285(8) 0.0016(7) 0.0061(7) -0.0012(6) C12 0.0357(9) 0.0247(8) 0.0261(8) 0.0003(6) -0.0006(7) -0.0021(6) C13 0.0368(9) 0.0249(8) 0.0334(9) -0.0011(7) 0.0068(7) 0.0041(7) N1 0.0528(10) 0.0248(7) 0.0331(8) -0.0082(6) -0.0141(7) 0.0046(7) O2 0.0435(10) 0.0700(12) 0.0665(12) -0.0181(9) -0.0177(8) -0.0001(8) C11 0.0278(8) 0.0341(8) 0.0405(10) 0.0040(7) 0.0088(7) -0.0031(7) C2 0.0285(8) 0.0328(8) 0.0267(8) 0.0044(6) 0.0009(6) -0.0047(7) C5 0.0272(8) 0.0293(9) 0.0374(9) -0.0015(7) 0.0062(7) -0.0014(7) O1 0.0896(14) 0.0645(11) 0.0327(8) 0.0015(7) -0.0090(9) 0.0040(11) C8 0.0349(9) 0.0258(8) 0.0302(9) -0.0045(6) -0.0062(7) 0.0043(7) C15 0.0634(14) 0.0238(8) 0.0292(9) 0.0011(7) -0.0018(9) 0.0033(8) C4 0.0321(8) 0.0270(9) 0.0481(11) -0.0053(8) 0.0033(8) 0.0072(7) _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 C9 1.7754(17) . ? S1 C7 1.8336(17) . ? C6 C5 1.388(2) . ? C6 C1 1.395(2) . ? C6 C7 1.511(2) . ? C7 C8 1.520(2) . ? C9 C14 1.380(2) . ? C9 C10 1.391(2) . ? C10 C11 1.380(3) . ? C1 C2 1.391(2) . ? C3 C2 1.381(3) . ? C3 C4 1.383(3) . ? O3 C12 1.358(2) . ? O3 C15 1.426(2) . ? C14 C13 1.392(3) . ? C12 C13 1.389(3) . ? C12 C11 1.393(3) . ? N1 O1 1.203(3) . ? N1 O2 1.207(3) . ? N1 C8 1.504(2) . ? C5 C4 1.385(3) . ? 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 C9 S1 C7 101.58(7) . . ? C5 C6 C1 118.87(15) . . ? C5 C6 C7 119.17(16) . . ? C1 C6 C7 121.95(15) . . ? C6 C7 C8 114.03(14) . . ? C6 C7 S1 106.70(11) . . ? C8 C7 S1 108.83(12) . . ? C14 C9 C10 119.36(15) . . ? C14 C9 S1 119.79(13) . . ? C10 C9 S1 120.78(13) . . ? C11 C10 C9 120.28(17) . . ? C2 C1 C6 120.31(16) . . ? C2 C3 C4 119.55(16) . . ? C12 O3 C15 117.72(15) . . ? C9 C14 C13 121.03(16) . . ? O3 C12 C13 124.03(17) . . ? O3 C12 C11 116.06(16) . . ? C13 C12 C11 119.91(16) . . ? C12 C13 C14 119.23(16) . . ? O1 N1 O2 123.4(2) . . ? O1 N1 C8 117.94(19) . . ? O2 N1 C8 118.67(19) . . ? C10 C11 C12 120.17(17) . . ? C3 C2 C1 120.27(16) . . ? C4 C5 C6 120.48(18) . . ? N1 C8 C7 109.80(14) . . ? C3 C4 C5 120.51(18) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 28.40 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.402 _refine_diff_density_min -0.170 _refine_diff_density_rms 0.053 # Attachment '- 6a.cif' data_6a _database_code_depnum_ccdc_archive 'CCDC 884840' #TrackingRef '- 6a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H17 N O4 S' _chemical_formula_weight 319.37 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 5.5219(8) _cell_length_b 12.1360(17) _cell_length_c 23.040(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1544.0(4) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 8051 _cell_measurement_theta_min 2.44 _cell_measurement_theta_max 28.31 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.70 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.374 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 672 _exptl_absorpt_coefficient_mu 0.227 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8573 _exptl_absorpt_correction_T_max 0.9560 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.366 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11444 _diffrn_reflns_av_R_equivalents 0.0239 _diffrn_reflns_av_sigmaI/netI 0.0230 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 28.30 _reflns_number_total 3849 _reflns_number_gt 3750 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0476P)^2^+0.3549P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _chemical_absolute_configuration ad _refine_ls_hydrogen_treatment constr _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 0.00(6) _refine_ls_number_reflns 3849 _refine_ls_number_parameters 201 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0334 _refine_ls_R_factor_gt 0.0324 _refine_ls_wR_factor_ref 0.0843 _refine_ls_wR_factor_gt 0.0833 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _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 C15 C 1.1193(3) -0.09193(13) 0.22072(8) 0.0373(4) Uani 1 1 d . . . H15A H 1.1081 -0.1262 0.1823 0.056 Uiso 1 1 calc R . . H15B H 1.1093 -0.1490 0.2507 0.056 Uiso 1 1 calc R . . H15C H 1.2740 -0.0529 0.2242 0.056 Uiso 1 1 calc R . . C16 C 0.3977(3) 0.20142(15) 0.25670(7) 0.0357(3) Uani 1 1 d . . . H16A H 0.4844 0.2709 0.2627 0.054 Uiso 1 1 calc R . . H16B H 0.3158 0.1801 0.2927 0.054 Uiso 1 1 calc R . . H16C H 0.2775 0.2108 0.2258 0.054 Uiso 1 1 calc R . . S1 S 0.76551(7) 0.33314(3) 0.052758(14) 0.02828(9) Uani 1 1 d . . . O4 O 0.9249(2) -0.01572(9) 0.22795(5) 0.0342(3) Uani 1 1 d . . . O3 O 0.5653(2) 0.11783(10) 0.24053(5) 0.0363(3) Uani 1 1 d . . . C6 C 0.9825(3) 0.51994(11) 0.01635(6) 0.0229(3) Uani 1 1 d . . . O2 O 1.0877(2) 0.66313(10) 0.15070(6) 0.0438(3) Uani 1 1 d . . . C9 C 0.8324(3) 0.23367(11) 0.10690(6) 0.0237(3) Uani 1 1 d . . . N1 N 1.1562(2) 0.57139(12) 0.13663(5) 0.0289(3) Uani 1 1 d . . . O1 O 1.3668(2) 0.54657(13) 0.13026(6) 0.0481(4) Uani 1 1 d . . . C13 C 0.7096(3) 0.13763(11) 0.19393(6) 0.0255(3) Uani 1 1 d . . . C7 C 1.0019(3) 0.43657(11) 0.06487(6) 0.0241(3) Uani 1 1 d . . . H7 H 1.1639 0.3999 0.0628 0.029 Uiso 1 1 calc R . . C12 C 0.6733(3) 0.22111(12) 0.15362(6) 0.0254(3) Uani 1 1 d . . . H12 H 0.5398 0.2699 0.1578 0.030 Uiso 1 1 calc R . . C4 C 0.7864(3) 0.59180(12) 0.01209(6) 0.0292(3) Uani 1 1 d . . . H4 H 0.6616 0.5897 0.0405 0.035 Uiso 1 1 calc R . . C2 C 0.7727(3) 0.66650(13) -0.03353(7) 0.0315(3) Uani 1 1 d . . . H2 H 0.6388 0.7153 -0.0362 0.038 Uiso 1 1 calc R . . C10 C 1.0313(3) 0.16488(12) 0.10159(6) 0.0264(3) Uani 1 1 d . . . H10 H 1.1419 0.1748 0.0704 0.032 Uiso 1 1 calc R . . C14 C 0.9077(3) 0.06577(11) 0.18746(6) 0.0255(3) Uani 1 1 d . . . C11 C 1.0693(3) 0.08108(12) 0.14196(6) 0.0263(3) Uani 1 1 d . . . H11 H 1.2062 0.0342 0.1383 0.032 Uiso 1 1 calc R . . C3 C 1.1480(3) 0.59883(13) -0.07110(7) 0.0328(3) Uani 1 1 d . . . H3 H 1.2726 0.6013 -0.0995 0.039 Uiso 1 1 calc R . . C5 C 1.1622(3) 0.52370(13) -0.02569(6) 0.0289(3) Uani 1 1 d . . . H5 H 1.2958 0.4746 -0.0234 0.035 Uiso 1 1 calc R . . C8 C 0.9680(3) 0.48511(12) 0.12552(6) 0.0258(3) Uani 1 1 d . . . H8A H 0.8046 0.5181 0.1288 0.031 Uiso 1 1 calc R . . H8B H 0.9817 0.4260 0.1549 0.031 Uiso 1 1 calc R . . C1 C 0.9529(3) 0.67009(13) -0.07507(6) 0.0303(3) Uani 1 1 d . . . H1 H 0.9430 0.7212 -0.1062 0.036 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 C15 0.0492(10) 0.0267(7) 0.0360(8) 0.0044(6) 0.0010(7) 0.0065(7) C16 0.0286(7) 0.0453(9) 0.0332(8) -0.0065(7) 0.0074(6) -0.0059(6) S1 0.03477(18) 0.02595(15) 0.02413(16) 0.00245(12) -0.00750(14) -0.00412(15) O4 0.0426(6) 0.0297(5) 0.0303(5) 0.0070(4) 0.0045(5) 0.0041(5) O3 0.0352(6) 0.0407(6) 0.0329(6) 0.0057(5) 0.0118(5) -0.0008(5) C6 0.0236(6) 0.0230(6) 0.0220(6) -0.0005(5) -0.0002(5) 0.0002(5) O2 0.0490(7) 0.0294(5) 0.0530(7) -0.0060(5) 0.0081(6) -0.0083(6) C9 0.0304(7) 0.0210(6) 0.0197(6) 0.0003(5) -0.0041(5) -0.0042(5) N1 0.0278(6) 0.0362(6) 0.0229(5) -0.0027(5) 0.0033(5) -0.0066(5) O1 0.0245(5) 0.0703(9) 0.0494(8) -0.0221(7) 0.0040(5) -0.0052(6) C13 0.0247(7) 0.0290(6) 0.0228(6) -0.0020(5) 0.0009(5) -0.0052(5) C7 0.0265(6) 0.0241(6) 0.0216(6) -0.0002(5) -0.0003(5) -0.0004(5) C12 0.0235(6) 0.0248(6) 0.0278(7) -0.0026(5) -0.0016(5) -0.0009(5) C4 0.0243(7) 0.0325(7) 0.0308(7) 0.0031(6) 0.0041(6) 0.0033(6) C2 0.0274(7) 0.0318(7) 0.0351(7) 0.0041(6) -0.0025(6) 0.0044(7) C10 0.0296(7) 0.0272(6) 0.0224(6) -0.0027(5) 0.0015(5) -0.0025(6) C14 0.0306(7) 0.0231(6) 0.0227(6) -0.0004(5) -0.0022(5) -0.0033(5) C11 0.0282(7) 0.0250(6) 0.0256(6) -0.0027(5) 0.0004(5) 0.0015(5) C3 0.0356(7) 0.0375(8) 0.0254(7) 0.0021(6) 0.0094(6) 0.0021(6) C5 0.0302(7) 0.0294(7) 0.0271(7) 0.0006(5) 0.0055(6) 0.0061(6) C8 0.0256(7) 0.0286(7) 0.0231(6) -0.0014(5) 0.0023(5) -0.0057(5) C1 0.0372(8) 0.0288(7) 0.0250(6) 0.0045(6) -0.0035(6) -0.0016(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 C15 O4 1.427(2) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 O3 1.423(2) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? S1 C9 1.7749(14) . ? S1 C7 1.8324(15) . ? O4 C14 1.3629(17) . ? O3 C13 1.3584(17) . ? C6 C5 1.387(2) . ? C6 C4 1.394(2) . ? C6 C7 1.5115(18) . ? O2 N1 1.2198(19) . ? C9 C10 1.385(2) . ? C9 C12 1.398(2) . ? N1 O1 1.2100(18) . ? N1 C8 1.4974(18) . ? C13 C12 1.389(2) . ? C13 C14 1.407(2) . ? C7 C8 1.5280(18) . ? C7 H7 1.0000 . ? C12 H12 0.9500 . ? C4 C2 1.390(2) . ? C4 H4 0.9500 . ? C2 C1 1.381(2) . ? C2 H2 0.9500 . ? C10 C11 1.394(2) . ? C10 H10 0.9500 . ? C14 C11 1.389(2) . ? C11 H11 0.9500 . ? C3 C1 1.384(2) . ? C3 C5 1.390(2) . ? C3 H3 0.9500 . ? C5 H5 0.9500 . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C1 H1 0.9500 . ? 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 O4 C15 H15A 109.5 . . ? O4 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? O4 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? O3 C16 H16A 109.5 . . ? O3 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? O3 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C9 S1 C7 102.15(6) . . ? C14 O4 C15 116.29(12) . . ? C13 O3 C16 117.53(12) . . ? C5 C6 C4 119.07(13) . . ? C5 C6 C7 119.19(13) . . ? C4 C6 C7 121.72(12) . . ? C10 C9 C12 120.06(13) . . ? C10 C9 S1 120.86(11) . . ? C12 C9 S1 118.97(11) . . ? O1 N1 O2 123.86(14) . . ? O1 N1 C8 118.19(14) . . ? O2 N1 C8 117.94(13) . . ? O3 C13 C12 124.96(13) . . ? O3 C13 C14 115.47(12) . . ? C12 C13 C14 119.57(13) . . ? C6 C7 C8 114.18(11) . . ? C6 C7 S1 107.18(9) . . ? C8 C7 S1 108.42(9) . . ? C6 C7 H7 109.0 . . ? C8 C7 H7 109.0 . . ? S1 C7 H7 109.0 . . ? C13 C12 C9 120.24(13) . . ? C13 C12 H12 119.9 . . ? C9 C12 H12 119.9 . . ? C2 C4 C6 120.22(13) . . ? C2 C4 H4 119.9 . . ? C6 C4 H4 119.9 . . ? C1 C2 C4 120.37(14) . . ? C1 C2 H2 119.8 . . ? C4 C2 H2 119.8 . . ? C9 C10 C11 119.99(13) . . ? C9 C10 H10 120.0 . . ? C11 C10 H10 120.0 . . ? O4 C14 C11 124.67(13) . . ? O4 C14 C13 115.56(13) . . ? C11 C14 C13 119.77(13) . . ? C14 C11 C10 120.31(13) . . ? C14 C11 H11 119.8 . . ? C10 C11 H11 119.8 . . ? C1 C3 C5 120.23(14) . . ? C1 C3 H3 119.9 . . ? C5 C3 H3 119.9 . . ? C6 C5 C3 120.45(14) . . ? C6 C5 H5 119.8 . . ? C3 C5 H5 119.8 . . ? N1 C8 C7 109.91(11) . . ? N1 C8 H8A 109.7 . . ? C7 C8 H8A 109.7 . . ? N1 C8 H8B 109.7 . . ? C7 C8 H8B 109.7 . . ? H8A C8 H8B 108.2 . . ? C2 C1 C3 119.67(13) . . ? C2 C1 H1 120.2 . . ? C3 C1 H1 120.2 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 28.30 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.273 _refine_diff_density_min -0.252 _refine_diff_density_rms 0.053