data_global _journal_coden_Cambridge 177 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'Maguire, Anita' 'Kissane, Marie' 'Murphy, Maureen' "O'Brien, Elisabeth" 'Chopra, Jay' 'Murphy, Linda' 'Collins, Stuart' 'Lawrence, Simon' _publ_contact_author_name 'Maguire, Anita ' _publ_contact_author_email a.maguire@ucc.ie _publ_section_title ; Addition-substitution reactions of 2-thio-3-chloroacrylamides with carbon, nitrogen, oxygen, sulfur and selenium nucleophiles ; # Attachment 'Maguire.cif' #===================================================================== data_compound_24a _database_code_depnum_ccdc_archive 'CCDC 795660' #TrackingRef 'Maguire.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H18 N2 O4 S' _chemical_formula_sum 'C14 H18 N2 O4 S' _chemical_formula_weight 310.36 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 Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.6949(16) _cell_length_b 9.6545(13) _cell_length_c 13.611(2) _cell_angle_alpha 73.20(3) _cell_angle_beta 83.98(4) _cell_angle_gamma 80.88(4) _cell_volume 706.0(2) _cell_formula_units_Z 2 _cell_measurement_temperature 125(2) _cell_measurement_reflns_used 2813 _cell_measurement_theta_min 2.3 _cell_measurement_theta_max 25.4 _exptl_crystal_description needle _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.460 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 328 _exptl_absorpt_coefficient_mu 0.247 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9522 _exptl_absorpt_correction_T_max 0.9522 _exptl_absorpt_process_details '(CrystalClear; Rigaku, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 125(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Saturn 724, partial X goniometer, ACTOR SM robot' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6184 _diffrn_reflns_av_R_equivalents 0.0491 _diffrn_reflns_av_sigmaI/netI 0.0589 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.34 _diffrn_reflns_theta_max 25.39 _reflns_number_total 2509 _reflns_number_gt 2176 _reflns_threshold_expression >2sigma(I) _computing_data_collection '(CrystalClear; Rigaku, 2004)' _computing_cell_refinement '(CrystalClear; Rigaku, 2004)' _computing_data_reduction '(CrystalClear; Rigaku, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'PLATON (Spek, 2009)' _computing_publication_material 'SHELXL-97; PLATON' _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^)+(0.0706P)^2^+1.6596P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2509 _refine_ls_number_parameters 191 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0786 _refine_ls_R_factor_gt 0.0683 _refine_ls_wR_factor_ref 0.1817 _refine_ls_wR_factor_gt 0.1750 _refine_ls_goodness_of_fit_ref 1.132 _refine_ls_restrained_S_all 1.132 _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 0.12093(17) -0.00669(10) 0.32647(7) 0.0196(3) Uani 1 1 d . . . O1 O 0.3678(5) 0.0128(3) 0.3258(2) 0.0244(7) Uani 1 1 d . . . O2 O 0.0190(5) -0.1020(3) 0.41721(19) 0.0232(6) Uani 1 1 d . . . O3 O -0.1580(5) 0.3479(3) 0.1479(2) 0.0299(7) Uani 1 1 d . . . O4 O -0.7562(5) 0.5186(3) 0.4020(2) 0.0268(7) Uani 1 1 d . . . N1 N 0.2322(6) 0.2803(3) 0.1708(2) 0.0224(8) Uani 1 1 d . . . H1 H 0.3419 0.2227 0.2101 0.027 Uiso 1 1 calc R . . N2 N -0.3844(6) 0.2925(3) 0.3838(2) 0.0215(7) Uani 1 1 d . . . C1 C 0.1047(7) -0.0805(4) 0.2228(3) 0.0203(8) Uani 1 1 d . . . C2 C 0.2839(8) -0.0687(4) 0.1456(3) 0.0261(9) Uani 1 1 d . . . H2 H 0.4128 -0.0174 0.1459 0.031 Uiso 1 1 calc R . . C3 C 0.2734(8) -0.1328(5) 0.0674(3) 0.0307(10) Uani 1 1 d . . . H3 H 0.3970 -0.1259 0.0143 0.037 Uiso 1 1 calc R . . C4 C 0.0873(8) -0.2055(5) 0.0659(3) 0.0288(10) Uani 1 1 d . . . H4 H 0.0808 -0.2476 0.0114 0.035 Uiso 1 1 calc R . . C5 C -0.0919(8) -0.2180(5) 0.1439(3) 0.0319(10) Uani 1 1 d . . . H5 H -0.2196 -0.2702 0.1434 0.038 Uiso 1 1 calc R . . C6 C -0.0857(8) -0.1549(5) 0.2223(3) 0.0278(10) Uani 1 1 d . . . H6 H -0.2095 -0.1621 0.2754 0.033 Uiso 1 1 calc R . . C7 C 0.0021(7) 0.2713(4) 0.2001(3) 0.0205(8) Uani 1 1 d . . . C8 C -0.0528(7) 0.1629(4) 0.2984(3) 0.0193(8) Uani 1 1 d . . . C9 C -0.2377(7) 0.1774(4) 0.3700(3) 0.0199(8) Uani 1 1 d . . . H9 H -0.2656 0.0880 0.4189 0.024 Uiso 1 1 calc R . . C10 C -0.3578(8) 0.4464(4) 0.3350(3) 0.0274(10) Uani 1 1 d . . . H10A H -0.2571 0.4555 0.2702 0.033 Uiso 1 1 calc R . . H10B H -0.2788 0.4846 0.3813 0.033 Uiso 1 1 calc R . . C11 C -0.5998(8) 0.5336(5) 0.3128(3) 0.0295(10) Uani 1 1 d . . . H11A H -0.5813 0.6379 0.2827 0.035 Uiso 1 1 calc R . . H11B H -0.6707 0.5009 0.2614 0.035 Uiso 1 1 calc R . . C12 C -0.7854(7) 0.3691(4) 0.4461(3) 0.0249(9) Uani 1 1 d . . . H12A H -0.8582 0.3341 0.3963 0.030 Uiso 1 1 calc R . . H12B H -0.8953 0.3598 0.5083 0.030 Uiso 1 1 calc R . . C13 C -0.5528(7) 0.2755(4) 0.4744(3) 0.0240(9) Uani 1 1 d . . . H13A H -0.4859 0.3042 0.5288 0.029 Uiso 1 1 calc R . . H13B H -0.5787 0.1720 0.5018 0.029 Uiso 1 1 calc R . . C14 C 0.3048(8) 0.3825(5) 0.0760(3) 0.0265(9) Uani 1 1 d . . . H14A H 0.2737 0.3495 0.0175 0.040 Uiso 1 1 calc R . . H14B H 0.4754 0.3880 0.0750 0.040 Uiso 1 1 calc R . . H14C H 0.2145 0.4792 0.0713 0.040 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 0.0230(6) 0.0186(5) 0.0163(5) -0.0042(4) -0.0037(4) 0.0003(4) O1 0.0216(15) 0.0250(15) 0.0258(15) -0.0058(12) -0.0066(11) -0.0001(12) O2 0.0327(16) 0.0200(14) 0.0142(13) -0.0025(11) -0.0022(11) 0.0005(12) O3 0.0282(16) 0.0342(17) 0.0206(15) -0.0005(13) -0.0046(12) 0.0044(13) O4 0.0273(16) 0.0229(15) 0.0279(16) -0.0052(12) 0.0011(12) -0.0015(12) N1 0.0241(19) 0.0189(17) 0.0201(17) 0.0006(13) -0.0037(13) -0.0006(14) N2 0.0208(17) 0.0197(17) 0.0214(17) -0.0048(14) 0.0020(13) 0.0009(13) C1 0.025(2) 0.0187(19) 0.0167(19) -0.0049(15) -0.0013(15) -0.0014(16) C2 0.031(2) 0.023(2) 0.022(2) -0.0037(17) 0.0019(17) -0.0019(17) C3 0.039(3) 0.028(2) 0.022(2) -0.0079(18) 0.0059(18) -0.0008(19) C4 0.040(3) 0.026(2) 0.020(2) -0.0084(17) -0.0037(18) 0.0027(19) C5 0.033(2) 0.038(3) 0.028(2) -0.013(2) -0.0065(19) -0.006(2) C6 0.027(2) 0.031(2) 0.025(2) -0.0108(18) 0.0006(17) 0.0001(18) C7 0.027(2) 0.0187(19) 0.0157(19) -0.0055(15) -0.0045(16) 0.0006(16) C8 0.022(2) 0.0179(19) 0.0166(19) -0.0031(15) -0.0039(15) 0.0001(16) C9 0.022(2) 0.019(2) 0.0187(19) -0.0045(15) -0.0040(15) -0.0031(16) C10 0.030(2) 0.021(2) 0.027(2) -0.0039(17) 0.0086(18) -0.0029(17) C11 0.036(3) 0.023(2) 0.026(2) -0.0036(18) 0.0003(18) 0.0013(18) C12 0.024(2) 0.022(2) 0.028(2) -0.0072(17) -0.0004(17) -0.0018(16) C13 0.027(2) 0.023(2) 0.020(2) -0.0041(16) 0.0035(16) -0.0033(17) C14 0.030(2) 0.028(2) 0.020(2) -0.0049(17) -0.0009(17) -0.0029(18) _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 O2 1.439(3) . ? S1 O1 1.446(3) . ? S1 C8 1.735(4) . ? S1 C1 1.771(4) . ? O3 C7 1.226(5) . ? O4 C11 1.415(5) . ? O4 C12 1.423(5) . ? N1 C7 1.338(5) . ? N1 C14 1.445(5) . ? N2 C9 1.327(5) . ? N2 C10 1.467(5) . ? N2 C13 1.467(5) . ? C1 C2 1.379(6) . ? C1 C6 1.394(6) . ? C2 C3 1.387(6) . ? C3 C4 1.366(6) . ? C4 C5 1.387(6) . ? C5 C6 1.379(6) . ? C7 C8 1.480(5) . ? C8 C9 1.376(5) . ? C10 C11 1.507(6) . ? C12 C13 1.499(6) . ? 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 S1 O1 117.78(17) . . ? O2 S1 C8 109.39(18) . . ? O1 S1 C8 109.20(18) . . ? O2 S1 C1 107.34(17) . . ? O1 S1 C1 105.75(18) . . ? C8 S1 C1 106.79(18) . . ? C11 O4 C12 109.8(3) . . ? C7 N1 C14 121.6(3) . . ? C9 N2 C10 126.5(3) . . ? C9 N2 C13 119.7(3) . . ? C10 N2 C13 111.5(3) . . ? C2 C1 C6 120.7(4) . . ? C2 C1 S1 120.0(3) . . ? C6 C1 S1 119.3(3) . . ? C1 C2 C3 119.2(4) . . ? C4 C3 C2 120.7(4) . . ? C3 C4 C5 120.0(4) . . ? C6 C5 C4 120.3(4) . . ? C5 C6 C1 119.1(4) . . ? O3 C7 N1 122.0(4) . . ? O3 C7 C8 120.8(4) . . ? N1 C7 C8 117.2(3) . . ? C9 C8 C7 127.3(3) . . ? C9 C8 S1 114.5(3) . . ? C7 C8 S1 118.1(3) . . ? N2 C9 C8 132.3(4) . . ? N2 C10 C11 109.5(3) . . ? O4 C11 C10 112.4(3) . . ? O4 C12 C13 111.9(3) . . ? N2 C13 C12 109.9(3) . . ? _diffrn_measured_fraction_theta_max 0.966 _diffrn_reflns_theta_full 25.39 _diffrn_measured_fraction_theta_full 0.966 _refine_diff_density_max 0.471 _refine_diff_density_min -0.424 _refine_diff_density_rms 0.090 #===END===================================================== data_38a _database_code_depnum_ccdc_archive 'CCDC 795661' #TrackingRef 'Maguire.cif' _audit_creation_method 'APEX2 v2010.1-2' _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C20 H25 N O4 S' _chemical_formula_sum 'C20 H25 N O4 S' _chemical_formula_iupac ? _chemical_formula_weight 375.47 _chemical_absolute_configuration ad _chemical_melting_point ? _space_group_crystal_system orthorhombic _space_group_name_H-M_alt 'P 21 21 21' _space_group_name_Hall 'P 2ac 2ab' loop_ _space_group_symop_operation_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 5.3188(18) _cell_length_b 12.594(4) _cell_length_c 29.209(10) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1956.6(12) _cell_formula_units_Z 4 _cell_measurement_reflns_used 509 _cell_measurement_theta_min 2.6442 _cell_measurement_theta_max 13.5990 _cell_measurement_temperature 150.(2) _exptl_crystal_description Needle _exptl_crystal_colour 'clear colourless' _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.04 _exptl_crystal_density_diffrn 1.275 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 0.190 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS)' _exptl_absorpt_correction_T_min 0.94 _exptl_absorpt_correction_T_max 0.99 _exptl_special_details ; The crystal was small and diffracted poorly, which is why there is a high value for Rint. ; _diffrn_ambient_temperature 150.(2) _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX II DUO' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 8.3333 _diffrn_reflns_number 16634 _diffrn_reflns_av_R_equivalents 0.1884 _diffrn_reflns_av_sigmaI/netI 0.1667 _diffrn_reflns_theta_min 1.39 _diffrn_reflns_theta_max 25.03 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 34 _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. ; _reflns_number_total 3455 _reflns_number_gt 1716 _reflns_threshold_expression >2sigma(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.1722 _refine_ls_R_factor_gt 0.0701 _refine_ls_wR_factor_gt 0.1259 _refine_ls_wR_factor_ref 0.1613 _refine_ls_goodness_of_fit_ref 0.992 _refine_ls_restrained_S_all 0.999 _refine_ls_number_reflns 3455 _refine_ls_number_parameters 244 _refine_ls_number_restraints 31 _refine_ls_hydrogen_treatment constr _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0567P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.332 _refine_diff_density_min -0.287 _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 -0.02(19) 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' _computing_cell_refinement 'SAINT V7.68A (Bruker AXS, 2009)' _computing_data_reduction 'SAINT V7.68A (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group S S1 0.8984(2) 0.37192(12) 0.82167(6) 0.0404(5) Uani d . 1 B . O O2 1.1730(6) 0.3971(3) 0.82523(17) 0.0572(13) Uani d . 1 . . C C3 0.8201(10) 0.2956(4) 0.8710(2) 0.0371(16) Uani d . 1 . . C C4 0.9868(12) 0.2886(5) 0.9075(2) 0.0535(19) Uani d . 1 . . H H4 1.1344 0.331 0.9079 0.064 Uiso calc R 1 . . C C5 0.9363(14) 0.2189(5) 0.9433(2) 0.056(2) Uani d . 1 . . H H5 1.0484 0.2141 0.9685 0.068 Uiso calc R 1 . . C C6 0.7239(14) 0.1574(6) 0.9420(3) 0.067(2) Uani d . 1 . . H H6 0.6909 0.1083 0.9659 0.081 Uiso calc R 1 . . C C7 0.5589(14) 0.1669(6) 0.9061(3) 0.073(3) Uani d . 1 . . H H7 0.4079 0.1265 0.9061 0.087 Uiso calc R 1 . . C C8 0.6089(12) 0.2336(5) 0.8702(3) 0.066(2) Uani d . 1 . . H H8 0.4974 0.2368 0.8449 0.079 Uiso calc R 1 . . C C9 0.7215(9) 0.4930(4) 0.83551(19) 0.0347(16) Uani d D 1 . . H H9 0.5392 0.478 0.8302 0.042 Uiso calc R 1 A 1 C C10 0.7529(12) 0.5256(5) 0.8851(2) 0.0431(18) Uani d . 1 B . O O12 0.9654(7) 0.5459(4) 0.89947(15) 0.0530(13) Uani d . 1 . . N N13 0.5428(8) 0.5274(4) 0.91087(19) 0.0392(14) Uani d D 1 . . H H13 0.3957 0.5201 0.8983 0.047 Uiso d RD 1 B . C C14 0.5356(10) 0.5601(4) 0.9576(2) 0.0333(15) Uani d . 1 B . C C15 0.7183(11) 0.5284(5) 0.9884(3) 0.0437(17) Uani d . 1 . . H H15 0.8519 0.4832 0.9792 0.052 Uiso calc R 1 B . C C16 0.7003(12) 0.5644(5) 1.0328(3) 0.0489(19) Uani d . 1 B . H H16 0.8277 0.5444 1.0539 0.059 Uiso calc R 1 . . C C17 0.5075(12) 0.6279(5) 1.0482(2) 0.0439(17) Uani d . 1 . . C C18 0.3299(11) 0.6569(5) 1.0167(3) 0.051(2) Uani d . 1 B . H H18 0.1949 0.7014 1.0259 0.062 Uiso calc R 1 . . C C19 0.3422(10) 0.6229(5) 0.9716(2) 0.0460(17) Uani d . 1 . . H H19 0.2155 0.6434 0.9504 0.055 Uiso calc R 1 B . C C20 0.4915(16) 0.6651(6) 1.0967(2) 0.073(2) Uani d . 1 B . H H20A 0.4059 0.7339 1.0978 0.109 Uiso calc R 1 . . H H20B 0.6614 0.6724 1.1093 0.109 Uiso calc R 1 . . H H20C 0.3968 0.6133 1.1148 0.109 Uiso calc R 1 . . C C21A 0.7963(15) 0.5865(5) 0.80462(19) 0.038(2) Uani d PD 0.6 B 1 H H21A 0.9616 0.6171 0.8143 0.046 Uiso calc PR 0.6 B 1 C C21B 0.8781(8) 0.5698(2) 0.80613(13) 0.038(2) Uani d PD 0.4 B 2 H H21B 1.0628 0.5645 0.8122 0.046 Uiso calc PR 0.4 B 2 O O22 0.8115(8) 0.5432(2) 0.75936(13) 0.0548(14) Uani d RD 1 . . C C23 1.0129(8) 0.5803(2) 0.73034(13) 0.088(3) Uani d RD 1 B . H H23A 1.1754 0.5602 0.7444 0.105 Uiso calc R 1 B 1 H H23B 1.0064 0.6588 0.729 0.105 Uiso calc R 1 B 1 C C24A 1.004(2) 0.5367(12) 0.6818(3) 0.076(4) Uani d PDU 0.6 B 1 H H24A 1.1459 0.5652 0.6642 0.114 Uiso calc PR 0.6 B 1 H H24B 0.846 0.5577 0.6672 0.114 Uiso calc PR 0.6 B 1 H H24C 1.0154 0.4591 0.6827 0.114 Uiso calc PR 0.6 B 1 C C24B 0.885(4) 0.559(2) 0.6840(4) 0.076(4) Uani d PDU 0.4 B 2 H H24D 0.9985 0.58 0.6592 0.114 Uiso calc PR 0.4 B 2 H H24E 0.7296 0.6007 0.682 0.114 Uiso calc PR 0.4 B 2 H H24F 0.8455 0.4835 0.6814 0.114 Uiso calc PR 0.4 B 2 O O25A 0.5979(13) 0.6636(5) 0.8095(3) 0.0417(17) Uani d PD 0.6 B 1 C C26A 0.687(2) 0.7538(7) 0.7833(4) 0.074(4) Uani d PD 0.6 B 1 H H26A 0.6909 0.7394 0.75 0.089 Uiso calc PR 0.6 B 1 H H26B 0.8543 0.7787 0.7937 0.089 Uiso calc PR 0.6 B 1 O O25B 0.7803(17) 0.6766(5) 0.8123(4) 0.0417(17) Uani d PD 0.4 B 2 C C26B 0.534(2) 0.7096(7) 0.7968(8) 0.074(4) Uani d PD 0.4 B 2 H H26C 0.4071 0.6746 0.8165 0.089 Uiso calc PR 0.4 B 2 H H26D 0.5096 0.6824 0.7653 0.089 Uiso calc PR 0.4 B 2 C C27 0.4781(15) 0.8298(6) 0.7965(3) 0.090(3) Uani d DU 1 . . H H27A 0.5043 0.8981 0.7812 0.135 Uiso calc PR 0.6 B 1 H H27B 0.4793 0.8404 0.8298 0.135 Uiso calc PR 0.6 B 1 H H27C 0.3158 0.8 0.7872 0.135 Uiso calc PR 0.6 B 1 H H27D 0.3068 0.8419 0.7854 0.135 Uiso calc PR 0.4 B 2 H H27E 0.5981 0.8659 0.7764 0.135 Uiso calc PR 0.4 B 2 H H27F 0.494 0.858 0.8277 0.135 Uiso calc PR 0.4 B 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 S1 0.0341(8) 0.0430(9) 0.0441(11) -0.0003(8) 0.0033(9) 0.0031(9) O2 0.0267(19) 0.082(3) 0.063(3) -0.0005(19) 0.009(2) 0.017(3) C3 0.039(3) 0.031(4) 0.042(5) 0.006(3) 0.006(3) 0.003(3) C4 0.054(4) 0.052(5) 0.054(5) -0.002(3) 0.004(4) 0.008(4) C5 0.072(5) 0.049(4) 0.047(5) 0.022(4) 0.003(4) 0.012(4) C6 0.066(5) 0.063(5) 0.072(6) 0.013(4) 0.024(5) 0.034(5) C7 0.051(4) 0.062(5) 0.105(8) 0.001(4) 0.007(5) 0.035(5) C8 0.040(4) 0.060(5) 0.098(7) 0.004(4) 0.002(4) 0.033(5) C9 0.032(3) 0.033(3) 0.039(5) -0.004(3) -0.002(3) 0.001(3) C10 0.045(4) 0.035(4) 0.050(5) -0.005(3) -0.004(4) 0.005(3) O12 0.036(2) 0.073(3) 0.050(3) -0.020(2) -0.002(2) -0.015(3) N13 0.028(3) 0.036(3) 0.054(4) -0.001(2) -0.004(3) 0.004(3) C14 0.034(3) 0.025(4) 0.041(4) -0.007(3) 0.002(3) -0.003(3) C15 0.041(4) 0.046(4) 0.045(5) 0.017(3) 0.003(4) 0.013(4) C16 0.054(4) 0.043(4) 0.050(6) 0.011(3) -0.002(4) 0.016(4) C17 0.053(4) 0.037(4) 0.042(5) 0.000(4) 0.004(4) 0.007(4) C18 0.045(4) 0.044(4) 0.065(6) 0.003(3) 0.010(4) -0.014(4) C19 0.035(3) 0.046(4) 0.058(5) 0.012(3) -0.008(3) -0.013(4) C20 0.112(6) 0.059(5) 0.047(6) 0.008(4) 0.027(5) 0.007(4) C21A 0.053(6) 0.026(4) 0.036(5) 0.000(4) -0.003(4) 0.009(4) C21B 0.053(6) 0.026(4) 0.036(5) 0.000(4) -0.003(4) 0.009(4) O22 0.087(4) 0.035(3) 0.042(3) -0.010(2) 0.010(3) 0.006(2) C23 0.100(6) 0.088(6) 0.074(7) -0.015(5) 0.026(6) 0.008(5) C24A 0.089(7) 0.071(6) 0.068(5) 0.002(6) 0.028(6) -0.012(5) C24B 0.089(7) 0.071(6) 0.068(5) 0.002(6) 0.028(6) -0.012(5) O25A 0.056(4) 0.029(3) 0.041(4) -0.002(4) 0.000(4) 0.007(3) C26A 0.068(9) 0.079(10) 0.077(10) 0.009(7) 0.013(8) 0.003(8) O25B 0.056(4) 0.029(3) 0.041(4) -0.002(4) 0.000(4) 0.007(3) C26B 0.068(9) 0.079(10) 0.077(10) 0.009(7) 0.013(8) 0.003(8) C27 0.109(6) 0.088(6) 0.073(6) 0.007(5) -0.025(5) 0.028(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_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag S1 O2 . 1.498(4) ? S1 C3 . 1.782(6) ? S1 C9 . 1.836(5) ? C3 C8 . 1.369(8) ? C3 C4 . 1.388(8) ? C4 C5 . 1.392(8) ? C4 H4 . 0.95 ? C5 C6 . 1.370(9) ? C5 H5 . 0.95 ? C6 C7 . 1.373(10) ? C6 H6 . 0.95 ? C7 C8 . 1.369(9) ? C7 H7 . 0.95 ? C8 H8 . 0.95 ? C9 C10 . 1.514(9) ? C9 C21A . 1.536(5) ? C9 C21B . 1.539(4) ? C9 H9 . 1.0 ? C10 O12 . 1.233(7) ? C10 N13 . 1.348(7) ? N13 C14 . 1.428(7) ? N13 H13 . 0.8694 ? C14 C19 . 1.359(7) ? C14 C15 . 1.383(8) ? C15 C16 . 1.377(9) ? C15 H15 . 0.95 ? C16 C17 . 1.376(8) ? C16 H16 . 0.95 ? C17 C18 . 1.368(9) ? C17 C20 . 1.495(9) ? C18 C19 . 1.387(9) ? C18 H18 . 0.95 ? C19 H19 . 0.95 ? C20 H20A . 0.98 ? C20 H20B . 0.98 ? C20 H20C . 0.98 ? C21A O22 . 1.432(5) ? C21A O25A . 1.441(5) ? C21A H21A . 1.0 ? C21B O22 . 1.4504 ? C21B O25B . 1.453(5) ? C21B H21B . 1.0 ? O22 C23 . 1.4439 ? C23 C24A . 1.522(5) ? C23 C24B . 1.537(5) ? C23 H23A . 0.99 ? C23 H23B . 0.99 ? C24A H24A . 0.98 ? C24A H24B . 0.98 ? C24A H24C . 0.98 ? C24B H24D . 0.98 ? C24B H24E . 0.98 ? C24B H24F . 0.98 ? O25A C26A . 1.450(5) ? C26A C27 . 1.517(5) ? C26A H26A . 0.99 ? C26A H26B . 0.99 ? O25B C26B . 1.447(5) ? C26B C27 . 1.543(5) ? C26B H26C . 0.99 ? C26B H26D . 0.99 ? C27 H27A . 0.98 ? C27 H27B . 0.98 ? C27 H27C . 0.98 ? C27 H27D . 0.98 ? C27 H27E . 0.98 ? C27 H27F . 0.98 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O2 S1 C3 . . 106.6(3) ? O2 S1 C9 . . 107.9(2) ? C3 S1 C9 . . 98.6(2) ? C8 C3 C4 . . 120.1(6) ? C8 C3 S1 . . 119.0(6) ? C4 C3 S1 . . 120.4(5) ? C3 C4 C5 . . 119.6(6) ? C3 C4 H4 . . 120.2 ? C5 C4 H4 . . 120.2 ? C6 C5 C4 . . 119.6(7) ? C6 C5 H5 . . 120.2 ? C4 C5 H5 . . 120.2 ? C5 C6 C7 . . 120.0(7) ? C5 C6 H6 . . 120.0 ? C7 C6 H6 . . 120.0 ? C8 C7 C6 . . 120.9(7) ? C8 C7 H7 . . 119.6 ? C6 C7 H7 . . 119.6 ? C3 C8 C7 . . 119.8(7) ? C3 C8 H8 . . 120.1 ? C7 C8 H8 . . 120.1 ? C10 C9 C21A . . 109.0(5) ? C10 C9 C21B . . 107.6(4) ? C10 C9 S1 . . 112.3(4) ? C21A C9 S1 . . 112.0(4) ? C21B C9 S1 . . 97.0(3) ? C10 C9 H9 . . 107.8 ? C21A C9 H9 . . 107.8 ? C21B C9 H9 . . 123.9 ? S1 C9 H9 . . 107.8 ? O12 C10 N13 . . 124.5(6) ? O12 C10 C9 . . 118.9(6) ? N13 C10 C9 . . 116.6(5) ? C10 N13 C14 . . 124.2(5) ? C10 N13 H13 . . 120.6 ? C14 N13 H13 . . 114.2 ? C19 C14 C15 . . 120.3(6) ? C19 C14 N13 . . 118.3(5) ? C15 C14 N13 . . 121.3(6) ? C16 C15 C14 . . 117.9(6) ? C16 C15 H15 . . 121.0 ? C14 C15 H15 . . 121.0 ? C17 C16 C15 . . 123.4(6) ? C17 C16 H16 . . 118.3 ? C15 C16 H16 . . 118.3 ? C18 C17 C16 . . 116.8(6) ? C18 C17 C20 . . 121.0(6) ? C16 C17 C20 . . 122.2(6) ? C17 C18 C19 . . 121.6(6) ? C17 C18 H18 . . 119.2 ? C19 C18 H18 . . 119.2 ? C14 C19 C18 . . 120.0(6) ? C14 C19 H19 . . 120.0 ? C18 C19 H19 . . 120.0 ? C17 C20 H20A . . 109.5 ? C17 C20 H20B . . 109.5 ? H20A C20 H20B . . 109.5 ? C17 C20 H20C . . 109.5 ? H20A C20 H20C . . 109.5 ? H20B C20 H20C . . 109.5 ? O22 C21A O25A . . 112.9(6) ? O22 C21A C9 . . 105.3(5) ? O25A C21A C9 . . 105.6(5) ? O22 C21A H21A . . 110.9 ? O25A C21A H21A . . 110.9 ? C9 C21A H21A . . 110.9 ? O22 C21B O25B . . 104.0(5) ? O22 C21B C9 . . 104.3(3) ? O25B C21B C9 . . 108.6(5) ? O22 C21B H21B . . 113.0 ? O25B C21B H21B . . 113.0 ? C9 C21B H21B . . 113.0 ? C21A O22 C23 . . 117.4(3) ? C23 O22 C21B . . 107.3 ? O22 C23 C24A . . 114.1(6) ? O22 C23 C24B . . 97.6(9) ? O22 C23 H23A . . 108.7 ? C24A C23 H23A . . 108.7 ? C24B C23 H23A . . 135.0 ? O22 C23 H23B . . 108.7 ? C24A C23 H23B . . 108.7 ? C24B C23 H23B . . 97.0 ? H23A C23 H23B . . 107.6 ? C23 C24A H24A . . 109.5 ? C23 C24A H24B . . 109.5 ? H24A C24A H24B . . 109.5 ? C23 C24A H24C . . 109.5 ? H24A C24A H24C . . 109.5 ? H24B C24A H24C . . 109.5 ? C23 C24B H24D . . 109.5 ? C23 C24B H24E . . 109.5 ? H24D C24B H24E . . 109.5 ? C23 C24B H24F . . 109.5 ? H24D C24B H24F . . 109.5 ? H24E C24B H24F . . 109.5 ? C21A O25A C26A . . 103.6(6) ? O25A C26A C27 . . 96.9(6) ? O25A C26A H26A . . 112.4 ? C27 C26A H26A . . 112.4 ? O25A C26A H26B . . 112.4 ? C27 C26A H26B . . 112.4 ? H26A C26A H26B . . 109.9 ? C26B O25B C21B . . 123.5(7) ? O25B C26B C27 . . 117.3(8) ? O25B C26B H26C . . 108.0 ? C27 C26B H26C . . 108.0 ? O25B C26B H26D . . 108.0 ? C27 C26B H26D . . 108.0 ? H26C C26B H26D . . 107.2 ? C26A C27 H27A . . 109.5 ? C26B C27 H27A . . 146.8 ? C26A C27 H27B . . 109.5 ? C26B C27 H27B . . 97.3 ? H27A C27 H27B . . 109.5 ? C26A C27 H27C . . 109.5 ? C26B C27 H27C . . 78.2 ? H27A C27 H27C . . 109.5 ? H27B C27 H27C . . 109.5 ? C26A C27 H27D . . 134.0 ? C26B C27 H27D . . 109.5 ? H27A C27 H27D . . 81.0 ? H27B C27 H27D . . 108.3 ? C26A C27 H27E . . 70.3 ? C26B C27 H27E . . 109.5 ? H27B C27 H27E . . 121.9 ? H27C C27 H27E . . 125.7 ? H27D C27 H27E . . 109.5 ? C26A C27 H27F . . 113.7 ? C26B C27 H27F . . 109.5 ? H27A C27 H27F . . 95.4 ? H27C C27 H27F . . 118.2 ? H27D C27 H27F . . 109.5 ? H27E C27 H27F . . 109.5 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag O2 S1 C3 C8 . . . . -159.3(5) ? C9 S1 C3 C8 . . . . 89.0(5) ? O2 S1 C3 C4 . . . . 12.6(6) ? C9 S1 C3 C4 . . . . -99.2(5) ? C8 C3 C4 C5 . . . . -0.7(10) ? S1 C3 C4 C5 . . . . -172.5(5) ? C3 C4 C5 C6 . . . . 0.6(10) ? C4 C5 C6 C7 . . . . -1.8(11) ? C5 C6 C7 C8 . . . . 3.1(12) ? C4 C3 C8 C7 . . . . 1.9(10) ? S1 C3 C8 C7 . . . . 173.8(6) ? C6 C7 C8 C3 . . . . -3.1(12) ? O2 S1 C9 C10 . . . . -66.7(4) ? C3 S1 C9 C10 . . . . 44.0(4) ? O2 S1 C9 C21A . . . . 56.3(5) ? C3 S1 C9 C21A . . . . 166.9(5) ? O2 S1 C9 C21B . . . . 45.6(4) ? C3 S1 C9 C21B . . . . 156.3(3) ? C21A C9 C10 O12 . . . . -64.7(7) ? C21B C9 C10 O12 . . . . -45.6(7) ? S1 C9 C10 O12 . . . . 59.9(7) ? C21A C9 C10 N13 . . . . 117.1(6) ? C21B C9 C10 N13 . . . . 136.2(5) ? S1 C9 C10 N13 . . . . -118.3(5) ? O12 C10 N13 C14 . . . . 4.5(10) ? C9 C10 N13 C14 . . . . -177.4(5) ? C10 N13 C14 C19 . . . . 137.6(6) ? C10 N13 C14 C15 . . . . -43.1(8) ? C19 C14 C15 C16 . . . . -1.6(9) ? N13 C14 C15 C16 . . . . 179.1(6) ? C14 C15 C16 C17 . . . . 1.6(10) ? C15 C16 C17 C18 . . . . -1.2(10) ? C15 C16 C17 C20 . . . . 179.4(6) ? C16 C17 C18 C19 . . . . 0.7(9) ? C20 C17 C18 C19 . . . . -179.9(6) ? C15 C14 C19 C18 . . . . 1.1(9) ? N13 C14 C19 C18 . . . . -179.5(5) ? C17 C18 C19 C14 . . . . -0.7(9) ? C10 C9 C21A O22 . . . . 168.5(5) ? C21B C9 C21A O22 . . . . 79.6(6) ? S1 C9 C21A O22 . . . . 43.6(7) ? C10 C9 C21A O25A . . . . -71.8(7) ? C21B C9 C21A O25A . . . . -160.7(10) ? S1 C9 C21A O25A . . . . 163.3(5) ? C10 C9 C21B O22 . . . . -172.3(3) ? C21A C9 C21B O22 . . . . -75.2(7) ? S1 C9 C21B O22 . . . . 71.6(2) ? C10 C9 C21B O25B . . . . -61.8(6) ? C21A C9 C21B O25B . . . . 35.3(8) ? S1 C9 C21B O25B . . . . -177.9(5) ? O25A C21A O22 C23 . . . . 104.5(5) ? C9 C21A O22 C23 . . . . -140.8(4) ? O25A C21A O22 C21B . . . . 166.7(12) ? C9 C21A O22 C21B . . . . -78.6(7) ? O25B C21B O22 C21A . . . . -36.8(9) ? C9 C21B O22 C21A . . . . 77.0(8) ? O25B C21B O22 C23 . . . . 88.0(4) ? C9 C21B O22 C23 . . . . -158.2(2) ? C21A O22 C23 C24A . . . . -175.7(8) ? C21B O22 C23 C24A . . . . 166.4(6) ? C21A O22 C23 C24B . . . . -154.2(10) ? C21B O22 C23 C24B . . . . -172.1(9) ? O22 C21A O25A C26A . . . . -70.5(9) ? C9 C21A O25A C26A . . . . 174.9(8) ? C21A O25A C26A C27 . . . . -173.6(8) ? O22 C21B O25B C26B . . . . 44.0(15) ? C9 C21B O25B C26B . . . . -66.7(15) ? C21B O25B C26B C27 . . . . -167.5(12) ? O25A C26A C27 C26B . . . . -17.2(12) ? O25B C26B C27 C26A . . . . 43.7(12) ? #===END=====================================================