# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Rawson, J.' _publ_contact_author_email jmr31@cam.ac.uk _publ_section_title ; Synthesis and Characterisation of 3,4-Dialkoxy-Substituted Benzo-1,3,2-Dithiazolyl Radicals ; _publ_author_name J.Rawson #=== END data_2 _database_code_depnum_ccdc_archive 'CCDC 776405' #TrackingRef 'dialkoxy-revised.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H8 N O2 S2' _chemical_formula_sum 'C8 H8 N O2 S2' _chemical_formula_weight 214.27 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' S S 0.1246 0.1234 '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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca 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' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 9.1530(2) _cell_length_b 10.0183(2) _cell_length_c 20.2430(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1856.23(8) _cell_formula_units_Z 8 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 9025 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description plate _exptl_crystal_colour black _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.533 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 888 _exptl_absorpt_coefficient_mu 0.537 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.862 _exptl_absorpt_correction_T_max 0.971 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(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 'Nonius Kappa CCD' _diffrn_measurement_method 'thin slice \w and \f scans' _diffrn_reflns_number 15162 _diffrn_reflns_av_R_equivalents 0.0673 _diffrn_reflns_av_sigmaI/netI 0.0413 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 3.00 _diffrn_reflns_theta_max 25.02 _reflns_number_total 1635 _reflns_number_gt 1270 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _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^)+(0.0253P)^2^+1.6388P] 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 1635 _refine_ls_number_parameters 120 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0620 _refine_ls_R_factor_gt 0.0387 _refine_ls_wR_factor_ref 0.0835 _refine_ls_wR_factor_gt 0.0741 _refine_ls_goodness_of_fit_ref 1.101 _refine_ls_restrained_S_all 1.101 _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 0.08649(7) 0.21704(6) 0.48881(3) 0.0269(2) Uani 1 1 d . . . N1 N 0.2626(2) 0.1897(2) 0.50120(11) 0.0290(6) Uani 1 1 d . . . S2 S 0.32869(7) 0.06040(7) 0.45987(4) 0.0296(2) Uani 1 1 d . . . C1 C 0.1720(3) 0.0130(2) 0.41677(13) 0.0229(6) Uani 1 1 d . . . C2 C 0.1631(3) -0.0899(3) 0.37038(13) 0.0252(6) Uani 1 1 d . . . H2A H 0.2469 -0.1416 0.3598 0.030 Uiso 1 1 calc R . . C3 C 0.0314(3) -0.1154(2) 0.34028(13) 0.0243(6) Uani 1 1 d . . . C4 C -0.0931(3) -0.0381(2) 0.35662(13) 0.0238(6) Uani 1 1 d . . . C5 C -0.0844(3) 0.0652(2) 0.40145(13) 0.0241(6) Uani 1 1 d . . . H5A H -0.1679 0.1177 0.4117 0.029 Uiso 1 1 calc R . . C6 C 0.0508(3) 0.0909(2) 0.43145(13) 0.0214(6) Uani 1 1 d . . . O1 O 0.00842(19) -0.21153(17) 0.29383(9) 0.0302(5) Uani 1 1 d . . . C7 C 0.1299(3) -0.2951(3) 0.27739(14) 0.0342(7) Uani 1 1 d . . . H7A H 0.0998 -0.3606 0.2441 0.051 Uiso 1 1 calc R . . H7B H 0.1636 -0.3419 0.3171 0.051 Uiso 1 1 calc R . . H7C H 0.2095 -0.2402 0.2597 0.051 Uiso 1 1 calc R . . O2 O -0.21817(19) -0.07412(18) 0.32441(9) 0.0323(5) Uani 1 1 d . . . C8 C -0.3506(3) -0.0098(3) 0.34340(16) 0.0406(8) Uani 1 1 d . . . H8A H -0.4323 -0.0481 0.3186 0.061 Uiso 1 1 calc R . . H8B H -0.3435 0.0859 0.3339 0.061 Uiso 1 1 calc R . . H8C H -0.3670 -0.0229 0.3908 0.061 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 0.0253(4) 0.0229(4) 0.0326(4) -0.0066(3) -0.0009(3) 0.0007(3) N1 0.0235(12) 0.0290(12) 0.0344(14) -0.0091(10) -0.0012(10) -0.0018(10) S2 0.0221(3) 0.0294(4) 0.0375(4) -0.0079(3) -0.0039(3) 0.0009(3) C1 0.0234(13) 0.0198(13) 0.0257(15) 0.0019(11) 0.0032(12) -0.0034(11) C2 0.0235(14) 0.0238(13) 0.0283(15) -0.0018(11) 0.0044(12) 0.0031(12) C3 0.0291(15) 0.0222(14) 0.0215(14) -0.0010(11) 0.0026(12) -0.0027(12) C4 0.0201(13) 0.0266(14) 0.0247(15) 0.0026(11) -0.0031(11) -0.0034(12) C5 0.0222(13) 0.0240(13) 0.0261(15) 0.0003(11) 0.0013(11) 0.0017(12) C6 0.0244(14) 0.0176(12) 0.0224(14) 0.0004(11) 0.0022(11) -0.0021(11) O1 0.0305(10) 0.0299(10) 0.0301(11) -0.0104(9) 0.0007(8) -0.0006(9) C7 0.0394(17) 0.0287(15) 0.0344(17) -0.0081(13) 0.0083(14) 0.0017(13) O2 0.0233(10) 0.0391(11) 0.0346(12) -0.0094(9) -0.0059(8) 0.0019(9) C8 0.0245(15) 0.0517(19) 0.046(2) -0.0077(15) -0.0080(14) 0.0063(15) _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 N1 1.654(2) . ? S1 C6 1.747(3) . ? N1 S2 1.656(2) . ? S2 C1 1.744(3) . ? C1 C6 1.389(3) . ? C1 C2 1.397(4) . ? C2 C3 1.375(4) . ? C2 H2A 0.9500 . ? C3 O1 1.362(3) . ? C3 C4 1.417(4) . ? C4 O2 1.366(3) . ? C4 C5 1.379(4) . ? C5 C6 1.402(3) . ? C5 H5A 0.9500 . ? O1 C7 1.431(3) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? O2 C8 1.426(3) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? 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 N1 S1 C6 99.38(11) . . ? S1 N1 S2 114.15(13) . . ? N1 S2 C1 99.50(12) . . ? C6 C1 C2 120.8(2) . . ? C6 C1 S2 113.38(19) . . ? C2 C1 S2 125.8(2) . . ? C3 C2 C1 119.1(2) . . ? C3 C2 H2A 120.5 . . ? C1 C2 H2A 120.5 . . ? O1 C3 C2 124.9(2) . . ? O1 C3 C4 115.0(2) . . ? C2 C3 C4 120.0(2) . . ? O2 C4 C5 124.1(2) . . ? O2 C4 C3 114.7(2) . . ? C5 C4 C3 121.2(2) . . ? C4 C5 C6 118.3(2) . . ? C4 C5 H5A 120.9 . . ? C6 C5 H5A 120.9 . . ? C1 C6 C5 120.6(2) . . ? C1 C6 S1 113.53(19) . . ? C5 C6 S1 125.84(19) . . ? C3 O1 C7 117.0(2) . . ? O1 C7 H7A 109.5 . . ? O1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? O1 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C4 O2 C8 117.7(2) . . ? O2 C8 H8A 109.5 . . ? O2 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? O2 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.249 _refine_diff_density_min -0.281 _refine_diff_density_rms 0.066 # Attachment 'dialkoxy-revised.cif' data_1 _database_code_depnum_ccdc_archive 'CCDC 776406' #TrackingRef 'dialkoxy-revised.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C7 H4 N O2 S2' _chemical_formula_sum 'C7 H4 N O2 S2' _chemical_formula_weight 198.23 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 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.1621(5) _cell_length_b 18.4695(6) _cell_length_c 12.0518(3) _cell_angle_alpha 90.00 _cell_angle_beta 109.845(1) _cell_angle_gamma 90.00 _cell_volume 2965.15(16) _cell_formula_units_Z 16 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 17674 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description plate _exptl_crystal_colour black _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.776 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1616 _exptl_absorpt_coefficient_mu 0.665 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.854 _exptl_absorpt_correction_T_max 0.991 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; The crystals were weakly diffracting, reducing the quantity and quality of data that could be obtained. ; _diffrn_ambient_temperature 180(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 'Nonius Kappa CCD' _diffrn_measurement_method 'thin slice \w and \f scans' _diffrn_reflns_number 29730 _diffrn_reflns_av_R_equivalents 0.1732 _diffrn_reflns_av_sigmaI/netI 0.1283 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.68 _diffrn_reflns_theta_max 23.26 _reflns_number_total 4256 _reflns_number_gt 2414 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _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^)+(0.0058P)^2^+8.5825P] 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 SHELXL _refine_ls_extinction_coef 0.00031(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4256 _refine_ls_number_parameters 434 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1486 _refine_ls_R_factor_gt 0.0678 _refine_ls_wR_factor_ref 0.1265 _refine_ls_wR_factor_gt 0.1033 _refine_ls_goodness_of_fit_ref 1.080 _refine_ls_restrained_S_all 1.080 _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 0.03452(16) 0.75560(10) 0.63355(18) 0.0405(6) Uani 1 1 d . . . N1 N 0.0107(5) 0.7379(3) 0.4935(5) 0.0403(17) Uani 1 1 d . . . S2 S 0.03288(15) 0.65277(11) 0.46589(17) 0.0384(5) Uani 1 1 d . . . C1 C 0.0627(5) 0.6693(4) 0.6924(6) 0.0288(18) Uani 1 1 d . . . C2 C 0.0849(5) 0.6521(4) 0.8111(6) 0.0326(18) Uani 1 1 d . . . H2A H 0.0838 0.6873 0.8682 0.039 Uiso 1 1 calc R . . C3 C 0.1084(5) 0.5808(4) 0.8402(6) 0.0333(19) Uani 1 1 d . . . C4 C 0.1092(5) 0.5291(4) 0.7563(6) 0.0292(18) Uani 1 1 d . . . C5 C 0.0893(5) 0.5450(4) 0.6415(6) 0.0316(19) Uani 1 1 d . . . H5A H 0.0920 0.5093 0.5860 0.038 Uiso 1 1 calc R . . C6 C 0.0645(5) 0.6175(4) 0.6084(6) 0.0298(18) Uani 1 1 d . . . O1 O 0.1352(4) 0.5502(3) 0.9506(4) 0.0457(15) Uani 1 1 d . . . C7 C 0.1426(7) 0.4744(4) 0.9322(6) 0.045(2) Uani 1 1 d . . . H7A H 0.0875 0.4483 0.9482 0.055 Uiso 1 1 calc R . . H7B H 0.2073 0.4556 0.9864 0.055 Uiso 1 1 calc R . . O2 O 0.1363(4) 0.4632(3) 0.8121(5) 0.0497(16) Uani 1 1 d . . . S3 S 0.27628(16) 0.77162(10) 0.67955(17) 0.0410(6) Uani 1 1 d . . . N2 N 0.2561(5) 0.7736(3) 0.5364(5) 0.0461(18) Uani 1 1 d . . . S4 S 0.26620(17) 0.69400(12) 0.47929(17) 0.0444(6) Uani 1 1 d . . . C8 C 0.3090(5) 0.6808(4) 0.7077(7) 0.0306(18) Uani 1 1 d . . . C9 C 0.3333(5) 0.6463(4) 0.8170(6) 0.0319(18) Uani 1 1 d . . . H9A H 0.3348 0.6718 0.8861 0.038 Uiso 1 1 calc R . . C10 C 0.3543(5) 0.5754(4) 0.8192(6) 0.0330(19) Uani 1 1 d . . . C11 C 0.3545(6) 0.5365(4) 0.7197(7) 0.038(2) Uani 1 1 d . . . C12 C 0.3308(5) 0.5686(4) 0.6101(6) 0.036(2) Uani 1 1 d . . . H12A H 0.3308 0.5426 0.5421 0.043 Uiso 1 1 calc R . . C13 C 0.3068(5) 0.6419(4) 0.6062(6) 0.0278(17) Uani 1 1 d . . . O3 O 0.3801(4) 0.5297(3) 0.9143(4) 0.0516(16) Uani 1 1 d . . . C14 C 0.3907(6) 0.4591(4) 0.8712(8) 0.048(2) Uani 1 1 d . . . H14A H 0.3386 0.4263 0.8805 0.058 Uiso 1 1 calc R . . H14B H 0.4574 0.4389 0.9164 0.058 Uiso 1 1 calc R . . O4 O 0.3800(4) 0.4655(3) 0.7482(5) 0.0517(16) Uani 1 1 d . . . S5 S 0.55209(16) 0.77658(10) 0.67957(17) 0.0383(5) Uani 1 1 d . . . N3 N 0.5253(5) 0.7891(3) 0.5364(5) 0.0420(17) Uani 1 1 d . . . S6 S 0.52537(15) 0.71391(11) 0.46239(16) 0.0369(5) Uani 1 1 d . . . C15 C 0.5645(5) 0.6829(4) 0.6873(6) 0.0250(17) Uani 1 1 d . . . C16 C 0.5847(5) 0.6405(4) 0.7884(6) 0.0299(18) Uani 1 1 d . . . H16A H 0.5879 0.6606 0.8622 0.036 Uiso 1 1 calc R . . C17 C 0.5996(5) 0.5684(4) 0.7754(6) 0.0311(18) Uani 1 1 d . . . C18 C 0.5948(6) 0.5382(4) 0.6689(7) 0.0343(19) Uani 1 1 d . . . C19 C 0.5723(5) 0.5768(4) 0.5668(6) 0.0309(19) Uani 1 1 d . . . H19A H 0.5677 0.5550 0.4938 0.037 Uiso 1 1 calc R . . C20 C 0.5562(5) 0.6525(4) 0.5774(6) 0.0279(17) Uani 1 1 d . . . O5 O 0.6196(4) 0.5166(3) 0.8606(4) 0.0446(15) Uani 1 1 d . . . C21 C 0.6317(6) 0.4505(4) 0.8065(6) 0.041(2) Uani 1 1 d . . . H21A H 0.5834 0.4139 0.8147 0.050 Uiso 1 1 calc R . . H21B H 0.7006 0.4315 0.8446 0.050 Uiso 1 1 calc R . . O6 O 0.6139(4) 0.4652(3) 0.6834(5) 0.0481(15) Uani 1 1 d . . . S7 S 0.79737(15) 0.78522(10) 0.70641(16) 0.0357(5) Uani 1 1 d . . . N4 N 0.7632(5) 0.8122(3) 0.5661(5) 0.0400(17) Uani 1 1 d . . . S8 S 0.75305(15) 0.74596(10) 0.47190(16) 0.0347(5) Uani 1 1 d . . . C22 C 0.8131(5) 0.6930(4) 0.6872(6) 0.0298(18) Uani 1 1 d . . . C23 C 0.8435(5) 0.6403(4) 0.7768(6) 0.0314(19) Uani 1 1 d . . . H23A H 0.8581 0.6521 0.8577 0.038 Uiso 1 1 calc R . . C24 C 0.8507(6) 0.5718(4) 0.7405(7) 0.0335(19) Uani 1 1 d . . . C25 C 0.8323(5) 0.5530(4) 0.6254(6) 0.0278(18) Uani 1 1 d . . . C26 C 0.8031(5) 0.6009(4) 0.5342(6) 0.0338(19) Uani 1 1 d . . . H26A H 0.7909 0.5873 0.4546 0.041 Uiso 1 1 calc R . . C27 C 0.7925(5) 0.6731(4) 0.5689(6) 0.0272(17) Uani 1 1 d . . . O7 O 0.8799(4) 0.5108(3) 0.8118(4) 0.0429(14) Uani 1 1 d . . . C28 C 0.8738(6) 0.4525(4) 0.7327(6) 0.043(2) Uani 1 1 d . . . H28A H 0.9389 0.4267 0.7554 0.051 Uiso 1 1 calc R . . H28B H 0.8217 0.4177 0.7363 0.051 Uiso 1 1 calc R . . O8 O 0.8491(4) 0.4800(3) 0.6160(4) 0.0396(13) 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 S1 0.0437(14) 0.0334(11) 0.0484(13) 0.0028(10) 0.0209(11) 0.0026(10) N1 0.043(4) 0.044(4) 0.030(4) 0.002(3) 0.008(3) 0.005(3) S2 0.0419(13) 0.0393(12) 0.0345(11) 0.0061(10) 0.0135(10) -0.0008(10) C1 0.026(5) 0.027(4) 0.038(5) 0.002(4) 0.017(4) 0.002(3) C2 0.033(5) 0.028(4) 0.035(5) -0.006(4) 0.011(4) -0.005(4) C3 0.031(5) 0.039(5) 0.025(4) 0.004(4) 0.004(4) -0.006(4) C4 0.031(5) 0.026(4) 0.026(4) 0.001(4) 0.004(4) 0.005(3) C5 0.036(5) 0.023(4) 0.039(5) -0.007(4) 0.016(4) 0.000(3) C6 0.018(4) 0.048(5) 0.025(4) -0.001(4) 0.009(4) -0.003(4) O1 0.066(4) 0.038(3) 0.032(3) 0.002(3) 0.015(3) 0.002(3) C7 0.065(6) 0.048(6) 0.021(5) 0.007(4) 0.011(4) -0.003(4) O2 0.072(5) 0.032(3) 0.043(4) 0.009(3) 0.016(3) 0.008(3) S3 0.0454(14) 0.0314(12) 0.0442(13) 0.0051(10) 0.0125(11) -0.0018(10) N2 0.059(5) 0.036(4) 0.043(4) 0.008(3) 0.017(4) -0.006(4) S4 0.0477(14) 0.0540(14) 0.0339(12) 0.0098(10) 0.0170(11) 0.0022(11) C8 0.019(4) 0.028(4) 0.044(5) 0.001(4) 0.011(4) -0.002(3) C9 0.039(5) 0.027(5) 0.032(5) -0.003(4) 0.015(4) -0.003(4) C10 0.025(5) 0.039(5) 0.031(5) 0.001(4) 0.005(4) -0.004(4) C11 0.033(5) 0.033(5) 0.048(6) -0.009(4) 0.014(4) -0.004(4) C12 0.027(5) 0.050(6) 0.026(5) -0.008(4) 0.004(4) -0.003(4) C13 0.022(4) 0.032(5) 0.026(4) 0.000(3) 0.004(4) 0.002(3) O3 0.075(5) 0.038(3) 0.037(3) 0.009(3) 0.013(3) 0.011(3) C14 0.046(6) 0.025(5) 0.066(6) 0.011(4) 0.009(5) 0.005(4) O4 0.071(5) 0.033(4) 0.045(4) -0.002(3) 0.011(3) 0.014(3) S5 0.0481(14) 0.0307(11) 0.0391(12) 0.0035(9) 0.0189(11) 0.0041(10) N3 0.051(5) 0.039(4) 0.035(4) 0.005(3) 0.013(3) 0.005(3) S6 0.0370(13) 0.0420(12) 0.0299(11) 0.0059(9) 0.0090(10) -0.0008(10) C15 0.019(4) 0.026(4) 0.028(4) -0.003(3) 0.005(3) 0.002(3) C16 0.036(5) 0.033(5) 0.024(4) -0.004(4) 0.015(4) -0.004(4) C17 0.030(5) 0.029(5) 0.032(5) 0.006(4) 0.007(4) -0.001(4) C18 0.031(5) 0.030(5) 0.044(5) -0.004(4) 0.017(4) -0.007(4) C19 0.030(5) 0.041(5) 0.022(4) -0.013(4) 0.011(4) -0.010(4) C20 0.020(4) 0.034(4) 0.029(4) 0.004(4) 0.007(4) 0.001(3) O5 0.073(4) 0.028(3) 0.031(3) 0.006(3) 0.015(3) 0.002(3) C21 0.051(6) 0.029(5) 0.041(5) 0.008(4) 0.012(4) 0.006(4) O6 0.065(4) 0.031(3) 0.050(4) -0.005(3) 0.021(3) 0.005(3) S7 0.0447(13) 0.0292(11) 0.0322(11) -0.0008(9) 0.0117(10) 0.0008(9) N4 0.059(5) 0.031(4) 0.029(4) 0.004(3) 0.013(3) 0.003(3) S8 0.0398(13) 0.0348(12) 0.0309(11) 0.0043(9) 0.0137(10) 0.0018(9) C22 0.031(5) 0.034(4) 0.028(4) -0.005(4) 0.014(4) -0.005(4) C23 0.035(5) 0.037(5) 0.022(4) -0.002(4) 0.010(4) 0.000(4) C24 0.036(5) 0.028(5) 0.040(5) 0.005(4) 0.019(4) -0.004(4) C25 0.025(5) 0.025(4) 0.031(5) -0.003(4) 0.007(4) -0.001(3) C26 0.031(5) 0.037(5) 0.033(4) -0.005(4) 0.009(4) -0.002(4) C27 0.019(4) 0.025(4) 0.040(5) 0.006(4) 0.013(4) 0.000(3) O7 0.064(4) 0.029(3) 0.034(3) 0.003(3) 0.014(3) 0.005(3) C28 0.053(6) 0.037(5) 0.035(5) 0.003(4) 0.013(4) 0.002(4) O8 0.043(4) 0.032(3) 0.039(3) 0.002(3) 0.007(3) 0.005(3) _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 N1 1.638(6) . ? S1 C1 1.735(7) . ? N1 S2 1.658(6) . ? S2 C6 1.747(7) . ? C1 C2 1.393(9) . ? C1 C6 1.399(9) . ? C2 C3 1.374(10) . ? C2 H2A 0.9500 . ? C3 O1 1.375(8) . ? C3 C4 1.393(10) . ? C4 C5 1.348(9) . ? C4 O2 1.380(8) . ? C5 C6 1.408(10) . ? C5 H5A 0.9500 . ? O1 C7 1.426(9) . ? C7 O2 1.434(8) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? S3 N2 1.650(6) . ? S3 C8 1.743(7) . ? N2 S4 1.649(7) . ? S4 C13 1.731(7) . ? C8 C9 1.396(9) . ? C8 C13 1.410(9) . ? C9 C10 1.341(10) . ? C9 H9A 0.9500 . ? C10 O3 1.370(8) . ? C10 C11 1.400(10) . ? C11 O4 1.372(9) . ? C11 C12 1.382(10) . ? C12 C13 1.392(10) . ? C12 H12A 0.9500 . ? O3 C14 1.429(9) . ? C14 O4 1.443(9) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? S5 N3 1.653(6) . ? S5 C15 1.738(7) . ? N3 S6 1.651(6) . ? S6 C20 1.728(7) . ? C15 C16 1.395(9) . ? C15 C20 1.407(9) . ? C16 C17 1.367(10) . ? C16 H16A 0.9500 . ? C17 O5 1.360(8) . ? C17 C18 1.380(10) . ? C18 C19 1.363(10) . ? C18 O6 1.374(8) . ? C19 C20 1.429(10) . ? C19 H19A 0.9500 . ? O5 C21 1.422(8) . ? C21 O6 1.444(8) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? S7 N4 1.669(6) . ? S7 C22 1.743(7) . ? N4 S8 1.642(6) . ? S8 C27 1.745(7) . ? C22 C27 1.404(9) . ? C22 C23 1.409(9) . ? C23 C24 1.355(10) . ? C23 H23A 0.9500 . ? C24 C25 1.366(9) . ? C24 O7 1.391(8) . ? C25 C26 1.361(9) . ? C25 O8 1.380(8) . ? C26 C27 1.421(9) . ? C26 H26A 0.9500 . ? O7 C28 1.423(8) . ? C28 O8 1.423(8) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? 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 N1 S1 C1 100.1(3) . . ? S1 N1 S2 114.2(4) . . ? N1 S2 C6 99.1(3) . . ? C2 C1 C6 122.3(6) . . ? C2 C1 S1 124.7(5) . . ? C6 C1 S1 112.9(5) . . ? C3 C2 C1 115.5(6) . . ? C3 C2 H2A 122.2 . . ? C1 C2 H2A 122.2 . . ? C2 C3 O1 127.2(7) . . ? C2 C3 C4 122.2(7) . . ? O1 C3 C4 110.6(6) . . ? C5 C4 O2 128.3(7) . . ? C5 C4 C3 123.0(7) . . ? O2 C4 C3 108.7(6) . . ? C4 C5 C6 116.4(6) . . ? C4 C5 H5A 121.8 . . ? C6 C5 H5A 121.8 . . ? C1 C6 C5 120.6(6) . . ? C1 C6 S2 113.3(5) . . ? C5 C6 S2 126.1(5) . . ? C3 O1 C7 105.3(5) . . ? O1 C7 O2 108.4(5) . . ? O1 C7 H7A 110.0 . . ? O2 C7 H7A 110.0 . . ? O1 C7 H7B 110.0 . . ? O2 C7 H7B 110.0 . . ? H7A C7 H7B 108.4 . . ? C4 O2 C7 106.1(5) . . ? N2 S3 C8 99.5(3) . . ? S4 N2 S3 114.1(4) . . ? N2 S4 C13 100.2(3) . . ? C9 C8 C13 120.9(6) . . ? C9 C8 S3 125.9(6) . . ? C13 C8 S3 113.2(5) . . ? C10 C9 C8 116.5(7) . . ? C10 C9 H9A 121.8 . . ? C8 C9 H9A 121.8 . . ? C9 C10 O3 127.8(7) . . ? C9 C10 C11 123.4(7) . . ? O3 C10 C11 108.8(6) . . ? O4 C11 C12 127.4(7) . . ? O4 C11 C10 110.7(7) . . ? C12 C11 C10 121.8(7) . . ? C11 C12 C13 115.3(7) . . ? C11 C12 H12A 122.3 . . ? C13 C12 H12A 122.3 . . ? C12 C13 C8 122.1(6) . . ? C12 C13 S4 125.0(5) . . ? C8 C13 S4 112.8(5) . . ? C10 O3 C14 106.8(6) . . ? O3 C14 O4 108.2(6) . . ? O3 C14 H14A 110.1 . . ? O4 C14 H14A 110.1 . . ? O3 C14 H14B 110.1 . . ? O4 C14 H14B 110.1 . . ? H14A C14 H14B 108.4 . . ? C11 O4 C14 105.2(6) . . ? N3 S5 C15 100.3(3) . . ? S6 N3 S5 113.8(4) . . ? N3 S6 C20 99.5(3) . . ? C16 C15 C20 121.7(6) . . ? C16 C15 S5 126.4(5) . . ? C20 C15 S5 111.9(5) . . ? C17 C16 C15 116.2(6) . . ? C17 C16 H16A 121.9 . . ? C15 C16 H16A 121.9 . . ? O5 C17 C16 126.8(6) . . ? O5 C17 C18 110.5(6) . . ? C16 C17 C18 122.7(7) . . ? C19 C18 O6 127.2(7) . . ? C19 C18 C17 123.4(7) . . ? O6 C18 C17 109.4(7) . . ? C18 C19 C20 115.3(6) . . ? C18 C19 H19A 122.4 . . ? C20 C19 H19A 122.4 . . ? C15 C20 C19 120.7(6) . . ? C15 C20 S6 114.2(5) . . ? C19 C20 S6 125.1(5) . . ? C17 O5 C21 106.5(5) . . ? O5 C21 O6 107.6(5) . . ? O5 C21 H21A 110.2 . . ? O6 C21 H21A 110.2 . . ? O5 C21 H21B 110.2 . . ? O6 C21 H21B 110.2 . . ? H21A C21 H21B 108.5 . . ? C18 O6 C21 105.9(5) . . ? N4 S7 C22 99.4(3) . . ? S8 N4 S7 113.9(3) . . ? N4 S8 C27 100.3(3) . . ? C27 C22 C23 120.1(6) . . ? C27 C22 S7 113.5(5) . . ? C23 C22 S7 126.4(5) . . ? C24 C23 C22 115.8(6) . . ? C24 C23 H23A 122.1 . . ? C22 C23 H23A 122.1 . . ? C23 C24 C25 123.8(7) . . ? C23 C24 O7 126.5(7) . . ? C25 C24 O7 109.7(6) . . ? C26 C25 C24 123.7(7) . . ? C26 C25 O8 125.6(6) . . ? C24 C25 O8 110.6(6) . . ? C25 C26 C27 114.0(6) . . ? C25 C26 H26A 123.0 . . ? C27 C26 H26A 123.0 . . ? C22 C27 C26 122.6(6) . . ? C22 C27 S8 112.8(5) . . ? C26 C27 S8 124.6(5) . . ? C24 O7 C28 105.1(5) . . ? O8 C28 O7 109.3(6) . . ? O8 C28 H28A 109.8 . . ? O7 C28 H28A 109.8 . . ? O8 C28 H28B 109.8 . . ? O7 C28 H28B 109.8 . . ? H28A C28 H28B 108.3 . . ? C25 O8 C28 105.0(5) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 23.26 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.460 _refine_diff_density_min -0.456 _refine_diff_density_rms 0.121