# Supplementary Material (ESI) for Medicinal Chemical Communications # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full MedChemComm _journal_coden_Cambridge 1476 _publ_contact_author_name 'Toma, Lucio' _publ_contact_author_email lucio.toma@unipv.it _publ_section_title ; Synthesis, modeling, and crystallographic study of 3,4-disubstituted-1,2,5-oxadiazoles and evaluation of their ability to decrease STAT3 activity ; _publ_author_name L.Toma # Attachment '- avs_739433.txt' data_avs2 _database_code_depnum_ccdc_archive 'CCDC 739433' #TrackingRef '- avs_739433.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common avs-0288 _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H10 Cl F3 N4 O2' _chemical_formula_weight 382.73 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 9.064(3) _cell_length_b 14.500(3) _cell_length_c 12.384(3) _cell_angle_alpha 90.00 _cell_angle_beta 99.570(10) _cell_angle_gamma 90.00 _cell_volume 1621.6(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.568 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 776 _exptl_absorpt_coefficient_mu 0.288 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _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 3916 _diffrn_reflns_av_R_equivalents 0.1344 _diffrn_reflns_av_sigmaI/netI 0.1212 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -1 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 25.97 _reflns_number_total 3166 _reflns_number_gt 1376 _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^)+(0.0897P)^2^+0.0000P] 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 SHELXL _refine_ls_extinction_coef 0.012(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3166 _refine_ls_number_parameters 276 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1771 _refine_ls_R_factor_gt 0.0493 _refine_ls_wR_factor_gt 0.1230 _refine_ls_goodness_of_fit_ref 0.972 _refine_ls_shift/su_max 0.156 _refine_ls_shift/su_mean 0.026 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 Cl1 Cl -0.23391(14) 0.34215(11) 1.31017(11) 0.0895(6) Uani 1 1 d . . . O2 O 0.3604(3) 0.1928(2) 0.8089(2) 0.0576(8) Uani 1 1 d . . . N3 N 0.1611(4) 0.2609(3) 0.8683(3) 0.0473(10) Uani 1 1 d . . . H3 H 0.079(6) 0.260(3) 0.865(4) 0.066(15) Uiso 1 1 d . . . N4 N 0.1258(4) 0.1356(3) 0.7570(3) 0.0487(10) Uani 1 1 d . . . H4 H 0.061(6) 0.131(3) 0.779(4) 0.063(16) Uiso 1 1 d . . . C1 C 0.2053(4) 0.3886(3) 1.0052(3) 0.0468(10) Uani 1 1 d . . . N2 N 0.3520(4) 0.3722(3) 0.8785(3) 0.0638(11) Uani 1 1 d . . . O1 O 0.3919(4) 0.4463(3) 0.9440(3) 0.0856(12) Uani 1 1 d . . . C30 C 0.0915(4) 0.3755(3) 1.0763(3) 0.0452(10) Uani 1 1 d . . . C5 C 0.1598(4) 0.0656(3) 0.6874(3) 0.0398(9) Uani 1 1 d . . . C10 C 0.2673(5) 0.0784(3) 0.6211(3) 0.0502(11) Uani 1 1 d . . . H10 H 0.320(4) 0.134(3) 0.624(3) 0.047(11) Uiso 1 1 d . . . C8 C 0.2155(5) -0.0711(3) 0.5455(3) 0.0495(11) Uani 1 1 d . . . C33 C -0.1097(4) 0.3560(4) 1.2178(3) 0.0582(13) Uani 1 1 d . . . C31 C 0.0322(4) 0.2916(4) 1.0920(3) 0.0521(11) Uani 1 1 d . . . H31 H 0.063(5) 0.239(3) 1.063(3) 0.054(12) Uiso 1 1 d . . . N1 N 0.3001(4) 0.4559(3) 1.0219(3) 0.0767(13) Uani 1 1 d . . . C11 C 0.2249(4) 0.1959(3) 0.8097(3) 0.0409(10) Uani 1 1 d . . . C9 C 0.2941(5) 0.0093(3) 0.5508(3) 0.0524(11) Uani 1 1 d . . . H9 H 0.367(5) 0.022(3) 0.504(3) 0.070(13) Uiso 1 1 d . . . C32 C -0.0696(5) 0.2806(4) 1.1644(4) 0.0586(12) Uani 1 1 d . . . H32 H -0.096(4) 0.219(3) 1.175(3) 0.034(10) Uiso 1 1 d . . . C35 C 0.0486(5) 0.4507(4) 1.1322(4) 0.0567(12) Uani 1 1 d . . . H35 H 0.084(4) 0.507(3) 1.121(3) 0.042(12) Uiso 1 1 d . . . C34 C -0.0522(5) 0.4407(4) 1.2036(4) 0.0614(13) Uani 1 1 d . . . H34 H -0.081(6) 0.495(4) 1.241(4) 0.086(16) Uiso 1 1 d . . . C7 C 0.1086(5) -0.0822(4) 0.6111(4) 0.0612(13) Uani 1 1 d . . . H7 H 0.057(5) -0.133(3) 0.602(3) 0.046(12) Uiso 1 1 d . . . C6 C 0.0804(5) -0.0143(3) 0.6807(4) 0.0550(12) Uani 1 1 d . . . H6 H 0.028(6) -0.028(3) 0.730(4) 0.078(15) Uiso 1 1 d . . . C2 C 0.2377(4) 0.3361(3) 0.9140(3) 0.0456(10) Uani 1 1 d . . . F1 F 0.1379(4) -0.2021(3) 0.4433(3) 0.1185(13) Uani 1 1 d . . . F3 F 0.2802(7) -0.1137(3) 0.3784(3) 0.158(2) Uani 1 1 d . . . F2 F 0.3621(4) -0.1965(3) 0.5136(3) 0.1218(14) Uani 1 1 d . . . C12 C 0.2504(7) -0.1439(4) 0.4713(4) 0.0705(14) 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 Cl1 0.0721(8) 0.1313(13) 0.0768(9) -0.0138(8) 0.0467(7) -0.0016(8) O2 0.0231(13) 0.082(2) 0.0702(18) -0.0214(17) 0.0140(12) 0.0001(14) N3 0.0217(16) 0.062(2) 0.061(2) -0.0152(18) 0.0138(16) -0.0029(17) N4 0.0250(16) 0.063(2) 0.063(2) -0.0160(19) 0.0197(16) -0.0081(17) C1 0.0320(19) 0.061(3) 0.049(2) -0.014(2) 0.0096(17) -0.010(2) N2 0.045(2) 0.081(3) 0.071(2) -0.026(2) 0.0270(18) -0.0248(19) O1 0.067(2) 0.104(3) 0.097(2) -0.046(2) 0.0464(19) -0.051(2) C30 0.0333(19) 0.060(3) 0.043(2) -0.010(2) 0.0081(17) -0.003(2) C5 0.037(2) 0.049(3) 0.036(2) -0.0007(19) 0.0120(16) 0.0034(19) C10 0.046(2) 0.053(3) 0.057(3) -0.001(2) 0.023(2) -0.008(2) C8 0.061(3) 0.050(3) 0.039(2) 0.001(2) 0.0139(19) 0.005(2) C33 0.039(2) 0.093(4) 0.046(2) -0.011(3) 0.0177(18) 0.002(2) C31 0.042(2) 0.066(3) 0.051(2) -0.017(2) 0.0155(19) -0.006(2) N1 0.062(2) 0.098(3) 0.078(3) -0.035(2) 0.036(2) -0.033(2) C11 0.0245(18) 0.058(3) 0.041(2) -0.002(2) 0.0110(16) 0.0020(19) C9 0.057(3) 0.057(3) 0.050(2) -0.001(2) 0.027(2) 0.005(2) C32 0.052(3) 0.064(3) 0.064(3) -0.010(3) 0.024(2) -0.011(2) C35 0.052(3) 0.063(3) 0.058(3) -0.009(3) 0.016(2) -0.003(3) C34 0.057(3) 0.076(4) 0.054(3) -0.019(3) 0.017(2) 0.006(3) C7 0.060(3) 0.054(3) 0.075(3) -0.010(3) 0.028(2) -0.014(3) C6 0.049(2) 0.059(3) 0.063(3) -0.003(3) 0.027(2) -0.013(2) C2 0.0216(16) 0.063(3) 0.054(2) -0.009(2) 0.0121(16) -0.0047(19) F1 0.102(3) 0.103(3) 0.150(3) -0.067(2) 0.019(2) -0.002(2) F3 0.309(7) 0.099(3) 0.093(3) -0.023(2) 0.116(3) 0.003(3) F2 0.105(3) 0.128(3) 0.131(3) -0.039(2) 0.016(2) 0.060(2) C12 0.082(4) 0.066(3) 0.069(3) -0.009(3) 0.027(3) 0.009(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 Cl1 C33 1.745(4) . ? O2 C11 1.231(4) . ? N3 C11 1.381(5) . ? N3 C2 1.374(5) . ? N4 C11 1.349(5) . ? N4 C5 1.406(5) . ? C1 N1 1.301(5) . ? C1 C2 1.435(5) . ? C1 C30 1.477(5) . ? N2 C2 1.304(5) . ? N2 O1 1.368(5) . ? O1 N1 1.382(4) . ? C30 C31 1.368(6) . ? C30 C35 1.390(6) . ? C5 C6 1.370(6) . ? C5 C10 1.387(5) . ? C10 C9 1.383(6) . ? C8 C7 1.373(6) . ? C8 C9 1.373(6) . ? C8 C12 1.476(6) . ? C33 C32 1.368(7) . ? C33 C34 1.368(7) . ? C31 C32 1.398(6) . ? C35 C34 1.380(6) . ? C7 C6 1.369(6) . ? F1 C12 1.330(6) . ? F3 C12 1.302(6) . ? F2 C12 1.311(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 C11 N3 C2 122.9(3) . . ? C11 N4 C5 125.3(3) . . ? N1 C1 C2 108.4(3) . . ? N1 C1 C30 120.7(3) . . ? C2 C1 C30 130.9(4) . . ? C2 N2 O1 105.5(3) . . ? N2 O1 N1 111.4(3) . . ? C31 C30 C35 119.5(4) . . ? C31 C30 C1 122.0(4) . . ? C35 C30 C1 118.4(4) . . ? C6 C5 C10 119.6(4) . . ? C6 C5 N4 119.6(3) . . ? C10 C5 N4 120.8(4) . . ? C9 C10 C5 119.2(4) . . ? C7 C8 C9 119.0(4) . . ? C7 C8 C12 121.8(5) . . ? C9 C8 C12 119.1(4) . . ? C32 C33 C34 122.2(4) . . ? C32 C33 Cl1 118.4(4) . . ? C34 C33 Cl1 119.4(3) . . ? C30 C31 C32 120.8(5) . . ? C1 N1 O1 105.6(3) . . ? O2 C11 N4 123.9(3) . . ? O2 C11 N3 122.4(4) . . ? N4 C11 N3 113.7(3) . . ? C8 C9 C10 121.0(4) . . ? C33 C32 C31 118.2(5) . . ? C34 C35 C30 120.4(5) . . ? C33 C34 C35 119.0(5) . . ? C6 C7 C8 120.7(5) . . ? C7 C6 C5 120.5(4) . . ? N2 C2 N3 124.2(4) . . ? N2 C2 C1 109.0(4) . . ? N3 C2 C1 126.8(3) . . ? F3 C12 F2 107.0(5) . . ? F3 C12 F1 104.5(5) . . ? F2 C12 F1 103.6(4) . . ? F3 C12 C8 113.7(4) . . ? F2 C12 C8 114.1(5) . . ? F1 C12 C8 113.0(4) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.96 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.393 _refine_diff_density_min -0.432 _refine_diff_density_rms 0.130 # Attachment '- 2a_739434.txt' data_fiomi-zan _database_code_depnum_ccdc_archive 'CCDC 739434' #TrackingRef '- 2a_739434.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common md30 _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H11 N3 O2' _chemical_formula_weight 217.23 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' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 6.619(2) _cell_length_b 20.540(3) _cell_length_c 8.364(5) _cell_angle_alpha 90.00 _cell_angle_beta 103.72(3) _cell_angle_gamma 90.00 _cell_volume 1104.7(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.35 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.306 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 456 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _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 2314 _diffrn_reflns_av_R_equivalents 0.0504 _diffrn_reflns_av_sigmaI/netI 0.0282 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.20 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2172 _reflns_number_gt 1395 _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^)+(0.0818P)^2^+0.1219P] 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 2172 _refine_ls_number_parameters 169 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0885 _refine_ls_R_factor_gt 0.0637 _refine_ls_wR_factor_ref 0.1571 _refine_ls_wR_factor_gt 0.1816 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.042 _refine_ls_shift/su_max 0.147 _refine_ls_shift/su_mean 0.008 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 O1 O -0.2400(3) 0.10115(11) 0.5186(3) 0.0909(7) Uani 1 1 d . . . O2 O 0.3556(3) 0.22881(8) 0.63231(17) 0.0695(5) Uani 1 1 d . . . N1 N -0.0617(4) 0.06930(11) 0.6000(3) 0.0766(7) Uani 1 1 d . . . N2 N -0.1903(3) 0.15612(11) 0.4413(3) 0.0745(6) Uani 1 1 d . . . N3 N 0.1097(3) 0.20512(9) 0.4055(2) 0.0511(5) Uani 1 1 d . . . C11 C 0.2780(3) 0.23871(10) 0.4873(2) 0.0532(6) Uani 1 1 d . . . C1 C 0.0920(3) 0.10268(11) 0.5742(3) 0.0543(6) Uani 1 1 d . . . C2 C 0.0102(3) 0.15728(10) 0.4749(2) 0.0480(5) Uani 1 1 d . . . C3 C 0.3085(5) 0.08117(17) 0.6380(5) 0.0815(9) Uani 1 1 d . . . C4 C 0.3629(6) 0.28661(18) 0.3832(3) 0.0865(11) Uani 1 1 d . . . H4A H 0.397(8) 0.272(2) 0.307(6) 0.16(2) Uiso 1 1 d . . . H4B H 0.247(5) 0.3082(17) 0.309(4) 0.111(11) Uiso 1 1 d . . . C6 C 0.7163(4) 0.32574(15) 0.5186(3) 0.0744(7) Uani 1 1 d . . . H6 H 0.7703 0.2886 0.4803 0.089 Uiso 1 1 calc R . . C5 C 0.5053(3) 0.33623(10) 0.4812(2) 0.0507(5) Uani 1 1 d . . . C10 C 0.4339(5) 0.39179(13) 0.5398(3) 0.0768(8) Uani 1 1 d . . . H10 H 0.2920 0.4004 0.5161 0.092 Uiso 1 1 calc R . . C9 C 0.5715(11) 0.43470(15) 0.6332(5) 0.1260(18) Uani 1 1 d . . . H9 H 0.5206 0.4723 0.6715 0.151 Uiso 1 1 calc R . . C8 C 0.7711(12) 0.4244(3) 0.6697(5) 0.151(3) Uani 1 1 d . . . H8 H 0.8608 0.4540 0.7346 0.181 Uiso 1 1 calc R . . C7 C 0.8472(5) 0.3703(3) 0.6129(5) 0.1246(17) Uani 1 1 d . . . H7 H 0.9900 0.3633 0.6379 0.150 Uiso 1 1 calc R . . H3 H 0.047(4) 0.2194(12) 0.306(3) 0.066(7) Uiso 1 1 d . . . H3A H 0.314(6) 0.040(2) 0.682(5) 0.157(16) Uiso 1 1 d . . . H3B H 0.379(6) 0.111(2) 0.728(5) 0.144(15) Uiso 1 1 d . . . H3C H 0.387(6) 0.079(2) 0.558(5) 0.145(16) Uiso 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 O1 0.0628(12) 0.0931(15) 0.1215(17) -0.0043(12) 0.0309(11) -0.0205(11) O2 0.0864(11) 0.0696(11) 0.0383(8) 0.0092(7) -0.0133(8) -0.0287(8) N1 0.0840(16) 0.0676(14) 0.0828(15) 0.0028(11) 0.0284(13) -0.0157(12) N2 0.0516(12) 0.0757(15) 0.0919(15) -0.0079(12) 0.0085(11) -0.0061(10) N3 0.0546(10) 0.0556(11) 0.0348(9) 0.0021(8) -0.0056(8) -0.0074(8) C11 0.0606(13) 0.0533(12) 0.0373(10) 0.0012(9) -0.0050(9) -0.0116(10) C1 0.0625(14) 0.0508(12) 0.0509(12) -0.0032(10) 0.0158(10) -0.0070(10) C2 0.0456(11) 0.0508(12) 0.0444(10) -0.0106(9) 0.0045(8) -0.0037(9) C3 0.0766(19) 0.071(2) 0.089(2) 0.0191(17) 0.0040(17) 0.0104(15) C4 0.112(2) 0.091(2) 0.0419(14) 0.0141(14) -0.0120(15) -0.0500(18) C6 0.0708(17) 0.0869(19) 0.0677(16) 0.0067(14) 0.0206(13) 0.0102(14) C5 0.0590(13) 0.0486(12) 0.0408(10) 0.0085(9) 0.0046(9) -0.0064(10) C10 0.093(2) 0.0667(17) 0.0754(17) 0.0171(14) 0.0295(15) 0.0193(15) C9 0.262(6) 0.0458(16) 0.077(2) -0.0116(16) 0.054(3) -0.026(3) C8 0.221(6) 0.150(5) 0.070(2) -0.003(3) 0.011(3) -0.127(5) C7 0.069(2) 0.206(5) 0.089(3) 0.029(3) -0.0004(18) -0.057(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 O1 N2 1.379(3) . ? O1 N1 1.380(3) . ? O2 C11 1.217(2) . ? N1 C1 1.287(3) . ? N2 C2 1.290(3) . ? N3 C11 1.351(3) . ? N3 C2 1.385(3) . ? C11 C4 1.508(3) . ? C1 C2 1.424(3) . ? C1 C3 1.474(4) . ? C4 C5 1.494(3) . ? C6 C5 1.374(3) . ? C6 C7 1.374(5) . ? C5 C10 1.369(3) . ? C10 C9 1.371(6) . ? C9 C8 1.301(7) . ? C8 C7 1.351(7) . ? 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 N2 O1 N1 110.41(17) . . ? C1 N1 O1 106.4(2) . . ? C2 N2 O1 105.1(2) . . ? C11 N3 C2 124.55(18) . . ? O2 C11 N3 121.5(2) . . ? O2 C11 C4 123.9(2) . . ? N3 C11 C4 114.62(18) . . ? N1 C1 C2 108.1(2) . . ? N1 C1 C3 121.3(2) . . ? C2 C1 C3 130.5(2) . . ? N2 C2 N3 119.2(2) . . ? N2 C2 C1 110.0(2) . . ? N3 C2 C1 130.62(19) . . ? C5 C4 C11 113.7(2) . . ? C5 C6 C7 119.6(3) . . ? C10 C5 C6 117.9(2) . . ? C10 C5 C4 122.6(3) . . ? C6 C5 C4 119.5(3) . . ? C5 C10 C9 120.0(3) . . ? C8 C9 C10 122.0(4) . . ? C9 C8 C7 119.6(4) . . ? C8 C7 C6 120.8(4) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.168 _refine_diff_density_min -0.180 _refine_diff_density_rms 0.035 # Attachment '- 3a_739435.txt' data_md34 _database_code_depnum_ccdc_archive 'CCDC 739435' #TrackingRef '- 3a_739435.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common md34 _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H11 N3 O3 S' _chemical_formula_weight 253.28 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 ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.589(2) _cell_length_b 10.096(2) _cell_length_c 10.981(2) _cell_angle_alpha 70.085(9) _cell_angle_beta 86.169(9) _cell_angle_gamma 74.027(9) _cell_volume 559.9(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.502 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 264 _exptl_absorpt_coefficient_mu 0.289 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _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 2803 _diffrn_reflns_av_R_equivalents 0.0868 _diffrn_reflns_av_sigmaI/netI 0.1677 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -1 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.23 _diffrn_reflns_theta_max 26.99 _reflns_number_total 2420 _reflns_number_gt 1023 _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^)+(0.0947P)^2^+0.0000P] 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 2420 _refine_ls_number_parameters 216 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1945 _refine_ls_R_factor_gt 0.0542 _refine_ls_wR_factor_ref 0.1784 _refine_ls_wR_factor_gt 0.1300 _refine_ls_goodness_of_fit_ref 0.944 _refine_ls_restrained_S_all 0.944 _refine_ls_shift/su_max 2.569 _refine_ls_shift/su_mean 0.028 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 0.1580(2) 0.20144(12) 0.89492(11) 0.0294(5) Uani 0.94(5) 1 d P . . O3 O 0.3801(6) 0.2282(3) 0.8337(3) 0.0429(15) Uani 0.98(6) 1 d P . . O2 O 0.0315(7) 0.1208(4) 0.8519(3) 0.0513(16) Uani 1.00(6) 1 d . . . N3 N 0.2223(8) 0.1076(5) 1.0492(4) 0.044(2) Uani 1.00(6) 1 d . . . O1 O 0.6296(8) 0.2162(5) 1.1945(4) 0.064(2) Uani 0.93(5) 1 d P . . N2 N 0.5070(8) 0.2265(5) 1.0847(4) 0.051(2) Uiso 0.97(6) 1 d P . . N1 N 0.5625(9) 0.1163(5) 1.3035(4) 0.051(2) Uani 0.96(5) 1 d P . . C1 C 0.4052(9) 0.0672(5) 1.2635(4) 0.0366(19) Uiso 1.00(6) 1 d . . . C2 C 0.3705(9) 0.1349(5) 1.1267(4) 0.0332(19) Uani 0.97(6) 1 d P . . C5 C -0.0834(9) 0.4841(5) 0.7631(5) 0.0375(19) Uani 0.99(6) 1 d P . . C3 C 0.2803(15) -0.0387(8) 1.3517(6) 0.050(3) Uani 0.99(7) 1 d P . . C6 C -0.2584(11) 0.4955(6) 0.6754(6) 0.048(2) Uani 1.00(6) 1 d P . . H6 H -0.362(13) 0.427(8) 0.701(6) 0.04(3) Uiso 0.73(18) 1 d P . . C10 C 0.0652(12) 0.5792(5) 0.7301(6) 0.043(3) Uani 1.00(6) 1 d P . . H10 H 0.181(12) 0.567(6) 0.792(6) 0.05(3) Uiso 1.0(2) 1 d . . . C4 C -0.0510(12) 0.3697(5) 0.8954(5) 0.038(3) Uani 0.93(6) 1 d P . . H4A H 0.051(15) 0.386(8) 0.960(9) 0.11(5) Uiso 1.0(3) 1 d . . . H4B H -0.201(12) 0.344(6) 0.922(5) 0.05(3) Uiso 0.96(19) 1 d P . . C9 C 0.0402(12) 0.6843(6) 0.6076(6) 0.052(3) Uani 1.00(6) 1 d . . . H9 H 0.161(14) 0.743(8) 0.584(6) 0.04(3) Uiso 0.72(19) 1 d P . . C7 C -0.2809(13) 0.6010(6) 0.5533(7) 0.057(3) Uani 0.98(6) 1 d P . . H7 H -0.414(16) 0.612(8) 0.491(8) 0.09(4) Uiso 1.0(2) 1 d . . . C8 C -0.1319(12) 0.6937(6) 0.5208(7) 0.054(3) Uani 0.99(6) 1 d P . . H8 H -0.153(15) 0.757(11) 0.441(11) 0.11(5) Uiso 1.0(3) 1 d . . . H3 H 0.169(12) 0.025(9) 1.076(6) 0.01(3) Uiso 0.60(16) 1 d P . . H31 H 0.351(10) -0.062(5) 1.436(7) 0.03(2) Uiso 0.84(18) 1 d P . . H32 H 0.305(10) -0.126(8) 1.330(5) 0.04(3) Uiso 0.9(2) 1 d P . . H33 H 0.11(2) -0.005(10) 1.326(9) 0.12(5) Uiso 1.0(3) 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 0.0403(8) 0.0243(6) 0.0248(7) -0.0059(4) 0.0083(5) -0.0151(5) O3 0.040(2) 0.041(2) 0.042(2) -0.0083(16) 0.0136(15) -0.0126(16) O2 0.076(3) 0.043(2) 0.041(2) -0.0094(16) -0.0012(18) -0.032(2) N3 0.054(3) 0.041(3) 0.038(3) -0.004(2) 0.000(2) -0.025(2) O1 0.085(4) 0.087(4) 0.046(3) -0.023(2) 0.009(2) -0.064(3) N1 0.058(4) 0.063(3) 0.045(3) -0.024(2) 0.007(2) -0.029(3) C2 0.040(3) 0.034(3) 0.034(3) -0.015(2) 0.007(2) -0.021(2) C5 0.039(3) 0.026(3) 0.046(3) -0.012(2) 0.016(2) -0.009(2) C3 0.071(6) 0.049(5) 0.027(4) -0.003(3) 0.002(3) -0.026(4) C6 0.043(4) 0.039(3) 0.065(4) -0.017(3) -0.002(3) -0.014(2) C10 0.049(4) 0.030(3) 0.051(4) -0.012(2) 0.003(3) -0.016(2) C4 0.045(5) 0.033(3) 0.037(3) -0.016(2) 0.019(3) -0.014(2) C9 0.050(4) 0.034(3) 0.065(5) -0.009(3) 0.018(3) -0.012(3) C7 0.059(5) 0.045(4) 0.057(5) -0.011(3) -0.009(3) -0.005(3) C8 0.069(5) 0.031(4) 0.046(5) -0.002(3) 0.008(3) -0.006(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 O2 1.417(4) . ? S1 O3 1.420(3) . ? S1 N3 1.642(4) . ? S1 C4 1.778(5) . ? N3 C2 1.367(6) . ? O1 N1 1.384(5) . ? O1 N2 1.385(6) . ? N2 C2 1.304(6) . ? N1 C1 1.285(6) . ? C1 C2 1.424(6) . ? C1 C3 1.478(7) . ? C5 C6 1.373(7) . ? C5 C10 1.380(7) . ? C5 C4 1.502(7) . ? C6 C7 1.387(9) . ? C10 C9 1.388(8) . ? C9 C8 1.362(9) . ? C7 C8 1.363(9) . ? 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 O3 119.0(2) . . ? O2 S1 N3 104.6(2) . . ? O3 S1 N3 108.7(2) . . ? O2 S1 C4 110.1(3) . . ? O3 S1 C4 109.3(2) . . ? N3 S1 C4 103.9(3) . . ? C2 N3 S1 125.0(4) . . ? N1 O1 N2 110.7(4) . . ? C2 N2 O1 104.8(4) . . ? C1 N1 O1 105.9(4) . . ? N1 C1 C2 109.1(4) . . ? N1 C1 C3 122.9(5) . . ? C2 C1 C3 128.0(5) . . ? N2 C2 N3 124.4(4) . . ? N2 C2 C1 109.5(4) . . ? N3 C2 C1 126.1(4) . . ? C6 C5 C10 119.9(5) . . ? C6 C5 C4 121.0(5) . . ? C10 C5 C4 119.1(5) . . ? C5 C6 C7 119.5(6) . . ? C5 C10 C9 119.8(6) . . ? C5 C4 S1 111.7(4) . . ? C8 C9 C10 119.9(6) . . ? C8 C7 C6 120.3(7) . . ? C9 C8 C7 120.5(6) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 26.99 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.529 _refine_diff_density_min -0.407 _refine_diff_density_rms 0.081