# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 data_global _journal_coden_Cambridge 1350 _publ_requested_journal CrystEngComm loop_ _publ_author_name 'Wales, Craig' 'Thomas, Lynne' 'Wilson, Chick' _publ_contact_author_name 'Chick Wilson' _publ_contact_author_address ; ; _publ_contact_author_email C.C.Wilson@bath.ac.uk # Attachment 'PXN 2FBA.cif' data_shelxl_PXN_2FBA _database_code_depnum_ccdc_archive 'CCDC 890547' #TrackingRef 'PXN 2FBA.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H13 N3 O4 S, C7 H5 F O2' _chemical_formula_sum 'C22 H18 F N3 O6 S' _chemical_formula_weight 471.45 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' 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.4319(13) _cell_length_b 11.4199(18) _cell_length_c 12.3466(19) _cell_angle_alpha 115.410(6) _cell_angle_beta 95.966(7) _cell_angle_gamma 100.016(7) _cell_volume 1036.0(3) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 29514 _cell_measurement_theta_min 1 _cell_measurement_theta_max 57.75 _exptl_crystal_description Plate _exptl_crystal_colour Colourless _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.511 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 488 _exptl_absorpt_coefficient_mu 0.213 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8485 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'SADABS (Blessing, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'Bruker Apex II CCD' _diffrn_measurement_method 'CCD; rotation images' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 29514 _diffrn_reflns_av_R_equivalents 0.1120 _diffrn_reflns_av_sigmaI/netI 0.0675 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 28.66 _reflns_number_total 5252 _reflns_number_gt 3808 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2 (2009)' _computing_cell_refinement 'Bruker APEX2 (2009)' _computing_data_reduction 'Bruker APEX2 (2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0555P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5252 _refine_ls_number_parameters 370 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0683 _refine_ls_R_factor_gt 0.0441 _refine_ls_wR_factor_ref 0.1062 _refine_ls_wR_factor_gt 0.0978 _refine_ls_goodness_of_fit_ref 0.961 _refine_ls_restrained_S_all 0.961 _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 H17 H 0.499(2) 0.8874(17) 0.6373(15) 0.017(5) Uiso 1 1 d . . . H15 H 0.100(2) 0.5986(19) 0.4081(18) 0.027(5) Uiso 1 1 d . . . H14 H -0.034(3) 0.6452(19) 0.5694(17) 0.028(5) Uiso 1 1 d . . . H16 H 0.367(2) 0.7174(19) 0.4428(18) 0.029(5) Uiso 1 1 d . . . H18 H 0.362(3) 1.110(2) 0.979(2) 0.050(7) Uiso 1 1 d . . . H7 H 0.585(2) 0.5685(19) 0.4195(17) 0.022(5) Uiso 1 1 d . . . H13 H 0.852(2) 0.0497(19) -0.0424(18) 0.028(5) Uiso 1 1 d . . . H12 H 0.824(3) -0.030(2) -0.1817(19) 0.032(6) Uiso 1 1 d . . . H11 H 1.009(2) 0.0459(19) -0.1110(17) 0.025(5) Uiso 1 1 d . . . H8 H 0.316(2) 0.4266(19) 0.3492(17) 0.028(5) Uiso 1 1 d . . . H2 H 1.392(2) 0.1356(19) -0.3967(18) 0.029(5) Uiso 1 1 d . . . H5 H 0.677(2) 0.232(2) 0.0072(18) 0.023(6) Uiso 1 1 d . . . H9 H 0.249(2) 0.2421(19) 0.1574(17) 0.023(5) Uiso 1 1 d . . . H3 H 1.544(3) 0.292(2) -0.2050(18) 0.034(6) Uiso 1 1 d . . . H4 H 1.423(2) 0.3904(18) -0.0409(17) 0.020(5) Uiso 1 1 d . . . H1 H 1.108(3) 0.085(2) -0.4201(19) 0.032(6) Uiso 1 1 d . . . H6 H 0.762(3) 0.505(2) 0.2880(19) 0.037(6) Uiso 1 1 d . . . H10 H 1.137(3) 0.498(2) 0.118(2) 0.054(7) Uiso 1 1 d . . . S1 S 0.88198(5) 0.16371(4) -0.26014(4) 0.01848(12) Uani 1 1 d . . . O4 O 0.95602(14) 0.45854(12) 0.17141(10) 0.0222(3) Uani 1 1 d . . . O3 O 1.19984(15) 0.47222(12) 0.06275(11) 0.0206(3) Uani 1 1 d . . . O2 O 0.81907(14) 0.27108(12) -0.26328(10) 0.0219(3) Uani 1 1 d . . . N1 N 0.86858(16) 0.16822(13) -0.12678(12) 0.0170(3) Uani 1 1 d . . . N3 N 0.46281(17) 0.26032(14) 0.11566(12) 0.0187(3) Uani 1 1 d . . . N2 N 0.71782(17) 0.29549(15) 0.06728(14) 0.0181(3) Uani 1 1 d . . . C9 C 0.8782(2) 0.35585(17) 0.07882(15) 0.0178(4) Uani 1 1 d . . . C8 C 0.9571(2) 0.29411(16) -0.02489(14) 0.0169(3) Uani 1 1 d . . . C13 C 0.3942(2) 0.40612(19) 0.30245(17) 0.0260(4) Uani 1 1 d . . . O1 O 0.81235(15) 0.03014(12) -0.35463(11) 0.0255(3) Uani 1 1 d . . . C6 C 1.0972(2) 0.20258(17) -0.24786(15) 0.0187(4) Uani 1 1 d . . . C7 C 1.1100(2) 0.35532(16) -0.02750(14) 0.0162(3) Uani 1 1 d . . . C4 C 1.3610(2) 0.33067(17) -0.11868(17) 0.0196(4) Uani 1 1 d . . . C14 C 0.3551(2) 0.29545(18) 0.19016(16) 0.0223(4) Uani 1 1 d . . . C15 C 0.8927(2) 0.04928(18) -0.11345(18) 0.0223(4) Uani 1 1 d . . . C10 C 0.6165(2) 0.33891(16) 0.15269(15) 0.0174(3) Uani 1 1 d . . . C11 C 0.6665(2) 0.45364(19) 0.26562(16) 0.0218(4) Uani 1 1 d . . . C5 C 1.1903(2) 0.29620(16) -0.13225(15) 0.0169(3) Uani 1 1 d . . . C1 C 1.1709(2) 0.14260(19) -0.34618(17) 0.0252(4) Uani 1 1 d . . . C12 C 0.5529(2) 0.48604(19) 0.34037(17) 0.0253(4) Uani 1 1 d . . . C3 C 1.4356(2) 0.27116(18) -0.21664(17) 0.0233(4) Uani 1 1 d . . . C2 C 1.3417(2) 0.17745(19) -0.32994(18) 0.0264(4) Uani 1 1 d . . . F1 F 0.05867(12) 0.81267(10) 0.78667(9) 0.0256(3) Uani 1 1 d . . . O6 O 0.29808(15) 1.03595(13) 0.91729(11) 0.0252(3) Uani 1 1 d . . . O5 O 0.53873(15) 1.03034(13) 0.85896(12) 0.0293(3) Uani 1 1 d . . . C16 C 0.3033(2) 0.86782(17) 0.71922(15) 0.0181(4) Uani 1 1 d . . . C21 C 0.3868(2) 0.83518(18) 0.62192(16) 0.0222(4) Uani 1 1 d . . . C17 C 0.1441(2) 0.79154(17) 0.69558(15) 0.0194(4) Uani 1 1 d . . . C22 C 0.3914(2) 0.98455(17) 0.83870(15) 0.0181(4) Uani 1 1 d . . . C20 C 0.3110(2) 0.73431(19) 0.50618(17) 0.0249(4) Uani 1 1 d . . . C19 C 0.1505(2) 0.66280(19) 0.48557(17) 0.0262(4) Uani 1 1 d . . . C18 C 0.0674(2) 0.69033(19) 0.58054(17) 0.0242(4) 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 0.0133(2) 0.0203(2) 0.0160(2) 0.00431(17) 0.00327(15) 0.00039(16) O4 0.0211(6) 0.0194(6) 0.0176(6) 0.0033(5) 0.0037(5) -0.0018(5) O3 0.0174(6) 0.0186(6) 0.0188(6) 0.0041(5) 0.0028(5) 0.0000(5) O2 0.0171(6) 0.0264(7) 0.0208(6) 0.0109(5) 0.0024(5) 0.0028(5) N1 0.0153(7) 0.0144(7) 0.0171(7) 0.0043(6) 0.0039(5) 0.0008(6) N3 0.0180(7) 0.0188(8) 0.0206(7) 0.0101(6) 0.0056(6) 0.0038(6) N2 0.0167(7) 0.0160(8) 0.0168(7) 0.0043(6) 0.0029(6) 0.0008(6) C9 0.0184(8) 0.0175(9) 0.0193(8) 0.0107(7) 0.0031(7) 0.0025(7) C8 0.0169(8) 0.0160(8) 0.0158(8) 0.0065(7) 0.0017(6) 0.0026(7) C13 0.0283(10) 0.0282(10) 0.0264(10) 0.0135(8) 0.0148(8) 0.0106(8) O1 0.0195(6) 0.0240(7) 0.0195(6) 0.0003(5) 0.0047(5) -0.0023(5) C6 0.0128(8) 0.0186(9) 0.0237(9) 0.0098(7) 0.0046(6) 0.0008(7) C7 0.0163(8) 0.0139(8) 0.0178(8) 0.0076(7) 0.0010(6) 0.0023(6) C4 0.0165(8) 0.0166(9) 0.0255(9) 0.0111(8) 0.0024(7) 0.0011(7) C14 0.0200(9) 0.0228(10) 0.0267(9) 0.0135(8) 0.0080(7) 0.0036(8) C15 0.0190(9) 0.0179(10) 0.0281(10) 0.0097(8) 0.0047(8) 0.0018(7) C10 0.0189(8) 0.0174(9) 0.0187(8) 0.0103(7) 0.0051(6) 0.0053(7) C11 0.0207(9) 0.0205(10) 0.0210(9) 0.0071(8) 0.0045(7) 0.0032(8) C5 0.0170(8) 0.0145(8) 0.0210(8) 0.0094(7) 0.0056(6) 0.0034(7) C1 0.0203(9) 0.0240(10) 0.0222(9) 0.0042(8) 0.0063(7) -0.0010(8) C12 0.0292(10) 0.0224(10) 0.0209(9) 0.0062(8) 0.0071(7) 0.0068(8) C3 0.0138(8) 0.0235(10) 0.0353(10) 0.0158(8) 0.0077(7) 0.0031(7) C2 0.0237(9) 0.0238(10) 0.0295(10) 0.0083(8) 0.0146(8) 0.0056(8) F1 0.0207(5) 0.0241(6) 0.0279(6) 0.0093(5) 0.0084(4) 0.0005(4) O6 0.0168(6) 0.0251(7) 0.0221(6) 0.0027(6) 0.0057(5) -0.0022(5) O5 0.0152(6) 0.0271(7) 0.0312(7) 0.0021(6) 0.0044(5) 0.0001(5) C16 0.0172(8) 0.0171(9) 0.0203(8) 0.0097(7) 0.0021(6) 0.0031(7) C21 0.0186(9) 0.0231(10) 0.0260(9) 0.0128(8) 0.0043(7) 0.0036(7) C17 0.0190(8) 0.0194(9) 0.0218(9) 0.0105(7) 0.0063(7) 0.0053(7) C22 0.0179(8) 0.0168(9) 0.0202(8) 0.0097(7) 0.0027(6) 0.0029(7) C20 0.0256(10) 0.0268(10) 0.0214(9) 0.0105(8) 0.0062(7) 0.0048(8) C19 0.0283(10) 0.0230(10) 0.0201(9) 0.0064(8) -0.0020(7) 0.0021(8) C18 0.0166(9) 0.0221(10) 0.0293(10) 0.0110(8) 0.0001(7) -0.0020(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 O2 1.4314(13) . ? S1 O1 1.4322(12) . ? S1 N1 1.6416(14) . ? S1 C6 1.7660(17) . ? O4 C9 1.2405(19) . ? O3 C7 1.3393(19) . ? O3 H10 0.89(2) . ? N1 C8 1.444(2) . ? N1 C15 1.481(2) . ? N3 C10 1.347(2) . ? N3 C14 1.347(2) . ? N2 C9 1.369(2) . ? N2 C10 1.405(2) . ? N2 H5 0.768(19) . ? C9 C8 1.464(2) . ? C8 C7 1.367(2) . ? C13 C14 1.373(3) . ? C13 C12 1.386(3) . ? C13 H8 0.92(2) . ? C6 C1 1.386(2) . ? C6 C5 1.401(2) . ? C7 C5 1.476(2) . ? C4 C3 1.386(2) . ? C4 C5 1.397(2) . ? C4 H4 0.932(18) . ? C14 H9 0.925(19) . ? C15 H13 0.97(2) . ? C15 H12 0.96(2) . ? C15 H11 0.98(2) . ? C10 C11 1.399(2) . ? C11 C12 1.386(2) . ? C11 H6 0.85(2) . ? C1 C2 1.394(3) . ? C1 H1 0.90(2) . ? C12 H7 0.991(18) . ? C3 C2 1.385(3) . ? C3 H3 0.88(2) . ? C2 H2 0.95(2) . ? F1 C17 1.3556(19) . ? O6 C22 1.317(2) . ? O6 H18 0.89(3) . ? O5 C22 1.215(2) . ? C16 C17 1.393(2) . ? C16 C21 1.400(2) . ? C16 C22 1.498(2) . ? C21 C20 1.385(2) . ? C21 H17 0.977(18) . ? C17 C18 1.383(2) . ? C20 C19 1.389(3) . ? C20 H16 0.92(2) . ? C19 C18 1.377(3) . ? C19 H15 0.916(19) . ? C18 H14 0.88(2) . ? 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 119.43(8) . . ? O2 S1 N1 107.00(7) . . ? O1 S1 N1 109.05(7) . . ? O2 S1 C6 109.10(8) . . ? O1 S1 C6 109.44(8) . . ? N1 S1 C6 101.26(8) . . ? C7 O3 H10 104.9(15) . . ? C8 N1 C15 114.18(13) . . ? C8 N1 S1 113.00(11) . . ? C15 N1 S1 116.17(11) . . ? C10 N3 C14 118.24(15) . . ? C9 N2 C10 126.90(15) . . ? C9 N2 H5 117.2(15) . . ? C10 N2 H5 115.9(15) . . ? O4 C9 N2 122.96(15) . . ? O4 C9 C8 120.09(15) . . ? N2 C9 C8 116.96(14) . . ? C7 C8 N1 120.10(14) . . ? C7 C8 C9 121.04(15) . . ? N1 C8 C9 118.84(14) . . ? C14 C13 C12 117.94(17) . . ? C14 C13 H8 120.1(12) . . ? C12 C13 H8 121.9(12) . . ? C1 C6 C5 121.58(15) . . ? C1 C6 S1 122.18(13) . . ? C5 C6 S1 116.24(12) . . ? O3 C7 C8 123.86(15) . . ? O3 C7 C5 114.23(14) . . ? C8 C7 C5 121.90(14) . . ? C3 C4 C5 120.58(16) . . ? C3 C4 H4 121.5(11) . . ? C5 C4 H4 117.8(11) . . ? N3 C14 C13 123.53(16) . . ? N3 C14 H9 114.6(12) . . ? C13 C14 H9 121.8(12) . . ? N1 C15 H13 109.7(12) . . ? N1 C15 H12 109.3(12) . . ? H13 C15 H12 104.4(16) . . ? N1 C15 H11 109.7(11) . . ? H13 C15 H11 113.6(17) . . ? H12 C15 H11 109.8(16) . . ? N3 C10 C11 121.93(16) . . ? N3 C10 N2 113.79(14) . . ? C11 C10 N2 124.27(15) . . ? C12 C11 C10 118.25(17) . . ? C12 C11 H6 119.6(15) . . ? C10 C11 H6 122.1(15) . . ? C4 C5 C6 118.14(15) . . ? C4 C5 C7 121.03(15) . . ? C6 C5 C7 120.82(14) . . ? C6 C1 C2 119.19(17) . . ? C6 C1 H1 119.5(13) . . ? C2 C1 H1 121.2(13) . . ? C11 C12 C13 120.11(18) . . ? C11 C12 H7 119.2(11) . . ? C13 C12 H7 120.7(11) . . ? C2 C3 C4 120.47(17) . . ? C2 C3 H3 120.5(13) . . ? C4 C3 H3 118.9(13) . . ? C3 C2 C1 120.02(17) . . ? C3 C2 H2 120.7(12) . . ? C1 C2 H2 119.3(12) . . ? C22 O6 H18 106.6(16) . . ? C17 C16 C21 117.23(15) . . ? C17 C16 C22 125.72(15) . . ? C21 C16 C22 117.02(15) . . ? C20 C21 C16 120.97(16) . . ? C20 C21 H17 120.9(10) . . ? C16 C21 H17 118.1(10) . . ? F1 C17 C18 117.11(15) . . ? F1 C17 C16 120.61(15) . . ? C18 C17 C16 122.27(16) . . ? O5 C22 O6 122.86(15) . . ? O5 C22 C16 121.43(15) . . ? O6 C22 C16 115.67(14) . . ? C21 C20 C19 120.03(17) . . ? C21 C20 H16 119.3(12) . . ? C19 C20 H16 120.6(12) . . ? C18 C19 C20 120.11(17) . . ? C18 C19 H15 120.4(12) . . ? C20 C19 H15 119.4(12) . . ? C19 C18 C17 119.34(17) . . ? C19 C18 H14 121.4(13) . . ? C17 C18 H14 119.3(13) . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 28.66 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.473 _refine_diff_density_min -0.474 _refine_diff_density_rms 0.066 # Attachment 'PXN 2MBA.cif' data_shelxl_PXN_2MBA _database_code_depnum_ccdc_archive 'CCDC 890548' #TrackingRef 'PXN 2MBA.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H13 N3 O4 S, C8 H8 O2 ' _chemical_formula_sum 'C23 H21 N3 O6 S' _chemical_formula_weight 467.49 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.512(3) _cell_length_b 9.602(3) _cell_length_c 14.260(5) _cell_angle_alpha 82.134(23) _cell_angle_beta 75.238(22) _cell_angle_gamma 73.081(22) _cell_volume 1075.7(6) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 27724 _cell_measurement_theta_min 1.488 _cell_measurement_theta_max 28.222 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.443 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 488 _exptl_absorpt_coefficient_mu 0.198 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8419 _exptl_absorpt_correction_T_max 1.0 _exptl_absorpt_process_details 'sadabs (Blessing, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'Bruker Apex II CCD' _diffrn_measurement_method 'CCD; rotation images' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 27724 _diffrn_reflns_av_R_equivalents 0.0790 _diffrn_reflns_av_sigmaI/netI 0.0716 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.48 _diffrn_reflns_theta_max 28.22 _reflns_number_total 5281 _reflns_number_gt 3924 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2 (2009)' _computing_cell_refinement 'Bruker APEX2 (2009)' _computing_data_reduction 'Bruker APEX2 (2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0422P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5281 _refine_ls_number_parameters 382 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0651 _refine_ls_R_factor_gt 0.0410 _refine_ls_wR_factor_ref 0.1010 _refine_ls_wR_factor_gt 0.0939 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _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 H3 H 0.236(2) -0.011(2) 0.6618(14) 0.021(5) Uiso 1 1 d . . . H14 H 0.820(2) 0.428(2) 0.3958(14) 0.016(4) Uiso 1 1 d . . . H18 H 0.530(2) 0.854(2) 0.0446(14) 0.018(4) Uiso 1 1 d . . . H12 H 1.306(2) 0.082(2) 0.2598(15) 0.025(5) Uiso 1 1 d . . . H19 H 0.256(2) 0.990(2) 0.0320(15) 0.030(5) Uiso 1 1 d . . . H9 H 1.404(2) 0.497(2) 0.0653(14) 0.019(5) Uiso 1 1 d . . . H15 H 0.786(2) 0.593(2) 0.3450(14) 0.023(5) Uiso 1 1 d . . . H21 H 0.070(2) 0.745(2) 0.2709(13) 0.016(4) Uiso 1 1 d . . . H2 H 0.058(3) 0.101(2) 0.5524(15) 0.030(5) Uiso 1 1 d . . . H10 H 1.629(3) 0.313(2) 0.1081(16) 0.034(6) Uiso 1 1 d . . . H1 H 0.141(2) 0.277(2) 0.4343(14) 0.021(5) Uiso 1 1 d . . . H11 H 1.580(3) 0.110(3) 0.2071(16) 0.037(6) Uiso 1 1 d . . . H13 H 0.975(3) 0.501(2) 0.3489(15) 0.030(5) Uiso 1 1 d . . . H17 H 0.604(3) 0.566(2) 0.2248(16) 0.029(5) Uiso 1 1 d . . . H6 H 0.614(3) 0.347(3) 0.5351(15) 0.030(5) Uiso 1 1 d . . . H4 H 0.484(2) 0.057(2) 0.6529(15) 0.025(5) Uiso 1 1 d . . . H7 H 0.714(3) 0.215(2) 0.4721(17) 0.036(6) Uiso 1 1 d . . . H5 H 0.294(3) 0.537(3) 0.3219(18) 0.040(6) Uiso 1 1 d . . . H20 H 0.020(3) 0.933(2) 0.1480(16) 0.036(6) Uiso 1 1 d . . . H16 H 1.022(3) 0.670(3) 0.024(2) 0.058(8) Uiso 1 1 d . . . H8 H 0.679(3) 0.190(2) 0.5910(15) 0.030(5) Uiso 1 1 d . . . S1 S 0.98110(5) 0.26473(4) 0.23043(3) 0.01594(11) Uani 1 1 d . . . O3 O 1.11729(15) 0.60434(13) 0.03107(8) 0.0193(3) Uani 1 1 d . . . O4 O 0.79497(14) 0.73761(13) 0.06533(9) 0.0220(3) Uani 1 1 d . . . O6 O 0.93532(14) 0.22212(12) 0.15016(9) 0.0199(3) Uani 1 1 d . . . O2 O 0.26376(15) 0.47590(14) 0.36509(10) 0.0234(3) Uani 1 1 d . . . O5 O 0.96141(14) 0.18128(13) 0.32241(9) 0.0207(3) Uani 1 1 d . . . O1 O 0.54129(14) 0.40255(14) 0.35896(9) 0.0237(3) Uani 1 1 d . . . N1 N 0.87551(16) 0.43607(15) 0.24736(10) 0.0161(3) Uani 1 1 d . . . N2 N 0.32093(17) 0.69379(15) 0.23106(10) 0.0184(3) Uani 1 1 d . . . C15 C 1.0741(2) 0.51882(17) 0.11052(11) 0.0158(3) Uani 1 1 d . . . N3 N 0.61110(17) 0.63509(16) 0.18223(11) 0.0176(3) Uani 1 1 d . . . C13 C 1.21741(19) 0.40321(18) 0.13646(11) 0.0158(3) Uani 1 1 d . . . C7 C 0.3997(2) 0.38735(18) 0.39379(12) 0.0176(3) Uani 1 1 d . . . C14 C 1.19177(19) 0.27784(18) 0.19325(12) 0.0165(3) Uani 1 1 d . . . C16 C 0.91192(19) 0.53276(17) 0.16284(12) 0.0156(3) Uani 1 1 d . . . C1 C 0.3590(2) 0.27295(18) 0.47070(12) 0.0173(3) Uani 1 1 d . . . C17 C 0.7692(2) 0.64377(18) 0.13247(12) 0.0174(3) Uani 1 1 d . . . C21 C 0.1640(2) 0.77218(19) 0.22269(13) 0.0203(3) Uani 1 1 d . . . C12 C 1.3833(2) 0.4172(2) 0.10507(12) 0.0186(3) Uani 1 1 d . . . C5 C 0.4151(2) 0.10326(19) 0.60657(13) 0.0220(4) Uani 1 1 d . . . C9 C 1.3252(2) 0.16857(19) 0.21993(12) 0.0202(3) Uani 1 1 d . . . C8 C 0.4655(2) 0.20622(18) 0.53538(12) 0.0177(3) Uani 1 1 d . . . C19 C 0.4358(2) 0.83528(19) 0.09215(13) 0.0209(4) Uani 1 1 d . . . C18 C 0.4543(2) 0.72543(17) 0.16678(12) 0.0169(3) Uani 1 1 d . . . C23 C 0.8635(2) 0.49238(19) 0.34189(12) 0.0186(3) Uani 1 1 d . . . C10 C 1.4890(2) 0.1849(2) 0.18786(13) 0.0230(4) Uani 1 1 d . . . C6 C 0.6281(2) 0.2434(2) 0.53243(14) 0.0228(4) Uani 1 1 d . . . C2 C 0.2084(2) 0.23334(19) 0.47895(13) 0.0206(4) Uani 1 1 d . . . C4 C 0.2680(2) 0.0626(2) 0.61367(13) 0.0240(4) Uani 1 1 d . . . C22 C 0.1339(2) 0.88298(19) 0.15075(13) 0.0219(4) Uani 1 1 d . . . C3 C 0.1645(2) 0.1271(2) 0.54897(13) 0.0231(4) Uani 1 1 d . . . C11 C 1.5174(2) 0.3086(2) 0.13066(12) 0.0214(4) Uani 1 1 d . . . C20 C 0.2727(2) 0.9141(2) 0.08467(14) 0.0246(4) 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 0.01189(19) 0.0160(2) 0.0194(2) 0.00272(15) -0.00445(15) -0.00393(14) O3 0.0175(6) 0.0205(6) 0.0178(6) 0.0041(5) -0.0020(5) -0.0062(5) O4 0.0176(6) 0.0208(6) 0.0244(7) 0.0062(5) -0.0036(5) -0.0046(5) O6 0.0170(6) 0.0180(6) 0.0259(6) 0.0011(5) -0.0080(5) -0.0050(5) O2 0.0166(6) 0.0254(7) 0.0277(7) 0.0101(6) -0.0076(5) -0.0077(5) O5 0.0161(6) 0.0207(6) 0.0228(6) 0.0064(5) -0.0038(5) -0.0052(5) O1 0.0160(6) 0.0278(7) 0.0260(7) 0.0076(5) -0.0047(5) -0.0082(5) N1 0.0129(6) 0.0165(7) 0.0178(7) 0.0029(5) -0.0040(5) -0.0038(5) N2 0.0159(7) 0.0198(7) 0.0197(7) 0.0002(6) -0.0052(6) -0.0047(6) C15 0.0181(8) 0.0155(8) 0.0154(8) -0.0003(6) -0.0050(6) -0.0061(6) N3 0.0146(7) 0.0162(7) 0.0200(7) 0.0048(6) -0.0043(6) -0.0034(5) C13 0.0151(8) 0.0198(8) 0.0131(7) -0.0015(6) -0.0027(6) -0.0058(6) C7 0.0170(8) 0.0186(8) 0.0182(8) -0.0022(6) -0.0048(6) -0.0054(6) C14 0.0120(7) 0.0212(8) 0.0159(8) -0.0012(6) -0.0026(6) -0.0044(6) C16 0.0165(8) 0.0141(7) 0.0165(8) 0.0011(6) -0.0053(6) -0.0040(6) C1 0.0158(8) 0.0178(8) 0.0167(8) -0.0028(6) -0.0005(6) -0.0039(6) C17 0.0166(8) 0.0163(8) 0.0195(8) -0.0007(6) -0.0041(6) -0.0046(6) C21 0.0171(8) 0.0203(8) 0.0232(9) -0.0023(7) -0.0042(7) -0.0046(7) C12 0.0171(8) 0.0231(9) 0.0156(8) -0.0004(7) -0.0019(6) -0.0075(7) C5 0.0202(8) 0.0224(9) 0.0219(9) 0.0014(7) -0.0059(7) -0.0035(7) C9 0.0185(8) 0.0214(9) 0.0196(8) 0.0024(7) -0.0068(7) -0.0031(7) C8 0.0162(8) 0.0180(8) 0.0172(8) -0.0029(6) -0.0022(6) -0.0027(6) C19 0.0179(8) 0.0204(8) 0.0235(9) 0.0019(7) -0.0044(7) -0.0055(7) C18 0.0159(8) 0.0161(8) 0.0198(8) -0.0030(6) -0.0050(6) -0.0041(6) C23 0.0164(8) 0.0211(9) 0.0175(8) -0.0005(7) -0.0034(7) -0.0045(7) C10 0.0145(8) 0.0297(10) 0.0223(9) -0.0008(7) -0.0060(7) -0.0011(7) C6 0.0197(9) 0.0275(10) 0.0229(9) 0.0024(8) -0.0081(8) -0.0081(7) C2 0.0182(8) 0.0229(9) 0.0207(9) -0.0004(7) -0.0050(7) -0.0057(7) C4 0.0245(9) 0.0220(9) 0.0228(9) 0.0037(7) -0.0014(7) -0.0078(7) C22 0.0181(8) 0.0169(8) 0.0300(10) -0.0024(7) -0.0090(7) -0.0005(7) C3 0.0176(8) 0.0266(9) 0.0256(9) -0.0007(7) -0.0021(7) -0.0096(7) C11 0.0141(8) 0.0317(10) 0.0189(8) -0.0030(7) -0.0020(7) -0.0077(7) C20 0.0263(9) 0.0190(9) 0.0283(10) 0.0049(7) -0.0116(8) -0.0041(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 O5 1.4384(13) . ? S1 O6 1.4415(12) . ? S1 N1 1.6462(15) . ? S1 C14 1.7723(17) . ? O3 C15 1.3422(19) . ? O3 H16 0.89(3) . ? O4 C17 1.2444(19) . ? O2 C7 1.3425(19) . ? O2 H5 0.84(2) . ? O1 C7 1.2240(19) . ? N1 C16 1.443(2) . ? N1 C23 1.489(2) . ? N2 C18 1.347(2) . ? N2 C21 1.355(2) . ? C15 C16 1.369(2) . ? C15 C13 1.479(2) . ? N3 C17 1.372(2) . ? N3 C18 1.416(2) . ? N3 H17 0.84(2) . ? C13 C14 1.396(2) . ? C13 C12 1.409(2) . ? C7 C1 1.493(2) . ? C14 C9 1.397(2) . ? C16 C17 1.479(2) . ? C1 C2 1.412(2) . ? C1 C8 1.417(2) . ? C21 C22 1.388(2) . ? C21 H21 0.987(18) . ? C12 C11 1.392(2) . ? C12 H9 0.920(19) . ? C5 C4 1.393(2) . ? C5 C8 1.393(2) . ? C5 H4 0.971(19) . ? C9 C10 1.400(2) . ? C9 H12 0.97(2) . ? C8 C6 1.516(2) . ? C19 C18 1.397(2) . ? C19 C20 1.398(2) . ? C19 H18 0.958(19) . ? C23 H14 0.982(19) . ? C23 H15 1.00(2) . ? C23 H13 1.01(2) . ? C10 C11 1.391(3) . ? C10 H11 0.96(2) . ? C6 H6 0.97(2) . ? C6 H7 0.99(2) . ? C6 H8 1.04(2) . ? C2 C3 1.390(2) . ? C2 H1 0.941(18) . ? C4 C3 1.397(2) . ? C4 H3 0.96(2) . ? C22 C20 1.390(3) . ? C22 H20 0.96(2) . ? C3 H2 1.00(2) . ? C11 H10 0.93(2) . ? C20 H19 0.98(2) . ? 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 O5 S1 O6 119.68(7) . . ? O5 S1 N1 108.81(8) . . ? O6 S1 N1 107.46(7) . . ? O5 S1 C14 108.72(7) . . ? O6 S1 C14 109.00(8) . . ? N1 S1 C14 101.67(8) . . ? C15 O3 H16 105.8(17) . . ? C7 O2 H5 109.0(15) . . ? C16 N1 C23 115.17(13) . . ? C16 N1 S1 112.73(11) . . ? C23 N1 S1 117.27(10) . . ? C18 N2 C21 118.44(14) . . ? O3 C15 C16 123.97(14) . . ? O3 C15 C13 114.19(14) . . ? C16 C15 C13 121.82(14) . . ? C17 N3 C18 127.41(14) . . ? C17 N3 H17 117.9(14) . . ? C18 N3 H17 114.6(14) . . ? C14 C13 C12 118.27(15) . . ? C14 C13 C15 120.90(14) . . ? C12 C13 C15 120.83(14) . . ? O1 C7 O2 121.69(15) . . ? O1 C7 C1 124.91(14) . . ? O2 C7 C1 113.39(14) . . ? C13 C14 C9 121.75(14) . . ? C13 C14 S1 116.60(12) . . ? C9 C14 S1 121.65(13) . . ? C15 C16 N1 120.68(14) . . ? C15 C16 C17 121.01(14) . . ? N1 C16 C17 118.28(14) . . ? C2 C1 C8 120.07(15) . . ? C2 C1 C7 118.18(14) . . ? C8 C1 C7 121.74(14) . . ? O4 C17 N3 123.46(14) . . ? O4 C17 C16 120.61(14) . . ? N3 C17 C16 115.94(14) . . ? N2 C21 C22 123.19(16) . . ? N2 C21 H21 115.8(10) . . ? C22 C21 H21 121.0(10) . . ? C11 C12 C13 120.47(16) . . ? C11 C12 H9 119.8(11) . . ? C13 C12 H9 119.7(11) . . ? C4 C5 C8 122.10(15) . . ? C4 C5 H4 118.1(11) . . ? C8 C5 H4 119.8(11) . . ? C14 C9 C10 118.95(16) . . ? C14 C9 H12 121.3(11) . . ? C10 C9 H12 119.7(11) . . ? C5 C8 C1 117.78(15) . . ? C5 C8 C6 118.66(14) . . ? C1 C8 C6 123.55(15) . . ? C18 C19 C20 118.27(16) . . ? C18 C19 H18 122.2(10) . . ? C20 C19 H18 119.5(10) . . ? N2 C18 C19 122.24(15) . . ? N2 C18 N3 113.18(14) . . ? C19 C18 N3 124.57(15) . . ? N1 C23 H14 109.8(11) . . ? N1 C23 H15 108.4(11) . . ? H14 C23 H15 110.0(15) . . ? N1 C23 H13 112.6(12) . . ? H14 C23 H13 109.6(15) . . ? H15 C23 H13 106.4(16) . . ? C11 C10 C9 120.20(16) . . ? C11 C10 H11 121.3(13) . . ? C9 C10 H11 118.5(13) . . ? C8 C6 H6 113.3(12) . . ? C8 C6 H7 112.3(12) . . ? H6 C6 H7 105.6(18) . . ? C8 C6 H8 110.6(11) . . ? H6 C6 H8 107.0(16) . . ? H7 C6 H8 107.7(17) . . ? C3 C2 C1 120.67(15) . . ? C3 C2 H1 120.5(11) . . ? C1 C2 H1 118.8(11) . . ? C5 C4 C3 119.97(16) . . ? C5 C4 H3 121.4(10) . . ? C3 C4 H3 118.6(10) . . ? C21 C22 C20 117.77(16) . . ? C21 C22 H20 119.3(13) . . ? C20 C22 H20 122.9(13) . . ? C2 C3 C4 119.37(16) . . ? C2 C3 H2 118.6(11) . . ? C4 C3 H2 122.1(11) . . ? C10 C11 C12 120.36(15) . . ? C10 C11 H10 117.7(13) . . ? C12 C11 H10 121.9(13) . . ? C22 C20 C19 120.09(16) . . ? C22 C20 H19 119.9(12) . . ? C19 C20 H19 120.0(12) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 28.22 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.424 _refine_diff_density_min -0.406 _refine_diff_density_rms 0.059 # Attachment 'PXN 3BRBA.cif' data_shelxl_PXN_3BRBA. _database_code_depnum_ccdc_archive 'CCDC 890549' #TrackingRef 'PXN 3BRBA.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H13 N3 O4 S, C7 H5 Br O2' _chemical_formula_sum 'C22 H18 Br N3 O6 S' _chemical_formula_weight 532.36 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' Br Br -0.2901 2.4595 '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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.2526(8) _cell_length_b 11.0759(10) _cell_length_c 13.7895(18) _cell_angle_alpha 101.575(5) _cell_angle_beta 105.505(6) _cell_angle_gamma 111.738(4) _cell_volume 1063.1(2) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 26239 _cell_measurement_theta_min 1 _cell_measurement_theta_max 52.95 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.663 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 540 _exptl_absorpt_coefficient_mu 2.079 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8581 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'SADABS (Blessing, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'Bruker Apex II CCD' _diffrn_measurement_method 'CCD; rotation images' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26239 _diffrn_reflns_av_R_equivalents 0.0958 _diffrn_reflns_av_sigmaI/netI 0.0605 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.63 _diffrn_reflns_theta_max 26.32 _reflns_number_total 4328 _reflns_number_gt 3370 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2 (2009)' _computing_cell_refinement 'Bruker APEX2 (2009)' _computing_data_reduction 'Bruker APEX2 (2009)' _computing_structure_solution SIR-92 _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^)+(0.0260P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4328 _refine_ls_number_parameters 370 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0470 _refine_ls_R_factor_gt 0.0305 _refine_ls_wR_factor_ref 0.0666 _refine_ls_wR_factor_gt 0.0629 _refine_ls_goodness_of_fit_ref 0.959 _refine_ls_restrained_S_all 0.959 _refine_ls_shift/su_max 0.030 _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 Br1 Br 0.68780(3) 0.91856(3) 0.13748(2) 0.02272(9) Uani 1 1 d . . . S1 S 0.56010(8) 0.39898(6) 0.27939(5) 0.01707(14) Uani 1 1 d . . . O2 O 0.0429(2) 0.46715(18) -0.12764(15) 0.0226(4) Uani 1 1 d . . . O4 O 0.5036(2) 0.39657(16) 0.36871(13) 0.0212(4) Uani 1 1 d . . . O3 O 0.4509(2) 0.28518(16) 0.18151(14) 0.0234(4) Uani 1 1 d . . . O1 O -0.1970(2) 0.52002(17) -0.14878(14) 0.0248(4) Uani 1 1 d . . . O5 O 1.0152(2) 0.79474(17) 0.47926(13) 0.0188(4) Uani 1 1 d . . . O6 O 0.7839(2) 0.89724(16) 0.42721(13) 0.0211(4) Uani 1 1 d . . . N2 N 0.4796(3) 0.7535(2) 0.30850(16) 0.0155(4) Uani 1 1 d . . . N3 N 0.5751(2) 0.54072(19) 0.25432(15) 0.0158(4) Uani 1 1 d . . . N1 N 0.2116(3) 0.78297(19) 0.26229(15) 0.0166(4) Uani 1 1 d . . . C19 C 1.0360(3) 0.3530(3) 0.3329(2) 0.0213(6) Uani 1 1 d . . . C20 C 1.1724(3) 0.4857(3) 0.3945(2) 0.0198(6) Uani 1 1 d . . . C9 C 0.2072(3) 1.0006(3) 0.3208(2) 0.0208(6) Uani 1 1 d . . . C16 C 0.9342(3) 0.5658(2) 0.38073(18) 0.0153(5) Uani 1 1 d . . . C21 C 1.1236(3) 0.5918(3) 0.41901(19) 0.0179(5) Uani 1 1 d . . . C14 C 0.7111(3) 0.6670(2) 0.34043(18) 0.0149(5) Uani 1 1 d . . . C15 C 0.8818(3) 0.6794(2) 0.39993(18) 0.0152(5) Uani 1 1 d . . . C13 C 0.6630(3) 0.7819(2) 0.36218(19) 0.0168(5) Uani 1 1 d . . . C2 C 0.1111(3) 0.6973(2) -0.03767(19) 0.0163(5) Uani 1 1 d . . . C8 C 0.1203(3) 0.8614(3) 0.2661(2) 0.0192(5) Uani 1 1 d . . . C10 C 0.4007(4) 1.0643(3) 0.3727(2) 0.0210(6) Uani 1 1 d . . . C6 C 0.1724(4) 0.9287(3) 0.0520(2) 0.0211(6) Uani 1 1 d . . . C12 C 0.3997(3) 0.8455(2) 0.31530(18) 0.0155(5) Uani 1 1 d . . . C1 C -0.0292(3) 0.5540(2) -0.10951(19) 0.0171(5) Uani 1 1 d . . . C18 C 0.8468(3) 0.3234(3) 0.2958(2) 0.0191(6) Uani 1 1 d . . . C11 C 0.5006(4) 0.9873(3) 0.3705(2) 0.0192(5) Uani 1 1 d . . . C22 C 0.5668(4) 0.5426(3) 0.1454(2) 0.0198(5) Uani 1 1 d . . . C3 C 0.3024(3) 0.7329(2) 0.00673(19) 0.0173(5) Uani 1 1 d . . . C5 C 0.3635(4) 0.9661(3) 0.0961(2) 0.0205(6) Uani 1 1 d . . . C17 C 0.7974(3) 0.4292(2) 0.32026(18) 0.0164(5) Uani 1 1 d . . . C7 C 0.0467(4) 0.7956(3) -0.0148(2) 0.0197(6) Uani 1 1 d . . . C4 C 0.4253(3) 0.8673(2) 0.07354(19) 0.0184(5) Uani 1 1 d . . . H3 H 0.450(3) 1.061(3) 0.141(2) 0.029(7) Uiso 1 1 d . . . H18 H 0.680(3) 0.552(2) 0.1342(18) 0.016(6) Uiso 1 1 d . . . H10 H 0.409(3) 0.669(2) 0.2678(18) 0.009(6) Uiso 1 1 d . . . H13 H 1.300(3) 0.509(2) 0.423(2) 0.024(7) Uiso 1 1 d . . . H14 H 1.220(3) 0.689(3) 0.461(2) 0.027(7) Uiso 1 1 d . . . H8 H 0.464(3) 1.158(3) 0.411(2) 0.028(7) Uiso 1 1 d . . . H2 H 0.344(3) 0.667(2) -0.0068(19) 0.019(7) Uiso 1 1 d . . . H5 H -0.076(4) 0.773(2) -0.040(2) 0.023(7) Uiso 1 1 d . . . H7 H 0.132(3) 1.051(2) 0.3240(19) 0.020(6) Uiso 1 1 d . . . H12 H 1.068(4) 0.274(3) 0.310(2) 0.037(8) Uiso 1 1 d . . . H6 H -0.007(3) 0.813(2) 0.2324(19) 0.019(7) Uiso 1 1 d . . . H11 H 0.757(3) 0.236(3) 0.2536(19) 0.019(7) Uiso 1 1 d . . . H9 H 0.629(3) 1.030(2) 0.4073(19) 0.020(7) Uiso 1 1 d . . . H16 H 0.556(3) 0.631(3) 0.1404(19) 0.028(7) Uiso 1 1 d . . . H17 H 0.460(3) 0.460(3) 0.091(2) 0.024(7) Uiso 1 1 d . . . H4 H 0.133(4) 0.991(3) 0.065(2) 0.033(8) Uiso 1 1 d . . . H15 H 0.980(4) 0.857(3) 0.480(2) 0.034(8) Uiso 1 1 d . . . H1 H -0.048(5) 0.390(3) -0.176(3) 0.062(11) 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 Br1 0.01303(14) 0.02258(15) 0.02672(15) 0.00762(11) 0.00339(11) 0.00524(11) S1 0.0122(3) 0.0136(3) 0.0228(3) 0.0038(3) 0.0041(3) 0.0061(2) O2 0.0132(9) 0.0181(10) 0.0308(11) 0.0013(8) 0.0044(8) 0.0075(8) O4 0.0177(9) 0.0211(9) 0.0299(10) 0.0120(8) 0.0123(8) 0.0097(7) O3 0.0170(9) 0.0174(9) 0.0294(10) 0.0028(8) 0.0022(8) 0.0084(7) O1 0.0138(9) 0.0224(10) 0.0305(10) -0.0003(8) 0.0026(8) 0.0087(7) O5 0.0154(9) 0.0140(9) 0.0219(10) 0.0020(8) 0.0013(7) 0.0073(8) O6 0.0173(9) 0.0163(9) 0.0244(10) 0.0024(8) 0.0022(8) 0.0081(7) N2 0.0122(10) 0.0109(10) 0.0207(12) 0.0026(9) 0.0047(9) 0.0047(9) N3 0.0129(10) 0.0157(10) 0.0174(11) 0.0032(9) 0.0032(9) 0.0078(8) N1 0.0131(10) 0.0173(11) 0.0194(11) 0.0055(9) 0.0064(9) 0.0071(8) C19 0.0229(14) 0.0254(14) 0.0210(14) 0.0074(12) 0.0074(11) 0.0170(12) C20 0.0140(13) 0.0280(14) 0.0207(14) 0.0098(12) 0.0061(11) 0.0121(11) C9 0.0224(14) 0.0232(14) 0.0245(14) 0.0097(12) 0.0105(12) 0.0160(12) C16 0.0141(12) 0.0175(12) 0.0160(13) 0.0074(10) 0.0061(10) 0.0077(10) C21 0.0156(13) 0.0187(13) 0.0178(13) 0.0057(11) 0.0054(11) 0.0069(11) C14 0.0140(12) 0.0141(12) 0.0160(13) 0.0045(10) 0.0052(10) 0.0061(10) C15 0.0146(12) 0.0151(12) 0.0135(12) 0.0044(10) 0.0058(10) 0.0042(10) C13 0.0153(13) 0.0179(13) 0.0174(13) 0.0065(11) 0.0071(11) 0.0068(11) C2 0.0159(12) 0.0188(13) 0.0157(13) 0.0064(10) 0.0070(10) 0.0081(10) C8 0.0145(13) 0.0228(14) 0.0230(14) 0.0077(11) 0.0079(11) 0.0104(11) C10 0.0238(14) 0.0163(13) 0.0200(14) 0.0036(11) 0.0044(11) 0.0100(11) C6 0.0244(15) 0.0219(14) 0.0230(14) 0.0088(12) 0.0096(12) 0.0154(12) C12 0.0162(13) 0.0197(13) 0.0162(13) 0.0084(11) 0.0082(11) 0.0111(10) C1 0.0164(13) 0.0190(13) 0.0181(13) 0.0079(11) 0.0075(11) 0.0086(11) C18 0.0174(13) 0.0178(14) 0.0202(14) 0.0033(11) 0.0057(11) 0.0086(11) C11 0.0155(13) 0.0215(13) 0.0200(14) 0.0058(11) 0.0052(11) 0.0093(11) C22 0.0169(14) 0.0199(14) 0.0208(14) 0.0029(11) 0.0068(12) 0.0087(11) C3 0.0171(13) 0.0194(13) 0.0177(13) 0.0064(11) 0.0070(11) 0.0101(11) C5 0.0217(14) 0.0164(13) 0.0181(14) 0.0051(11) 0.0043(11) 0.0057(11) C17 0.0148(12) 0.0205(13) 0.0157(13) 0.0073(11) 0.0061(10) 0.0090(10) C7 0.0146(13) 0.0233(14) 0.0213(14) 0.0083(11) 0.0050(11) 0.0092(11) C4 0.0127(12) 0.0235(13) 0.0188(13) 0.0096(11) 0.0053(10) 0.0072(10) _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 Br1 C4 1.913(2) . ? S1 O4 1.4303(17) . ? S1 O3 1.4311(17) . ? S1 N3 1.6420(19) . ? S1 C17 1.765(2) . ? O2 C1 1.323(3) . ? O2 H1 0.87(3) . ? O1 C1 1.218(3) . ? O5 C15 1.340(3) . ? O5 H15 0.84(3) . ? O6 C13 1.245(3) . ? N2 C13 1.376(3) . ? N2 C12 1.405(3) . ? N2 H10 0.86(2) . ? N3 C14 1.443(3) . ? N3 C22 1.490(3) . ? N1 C8 1.347(3) . ? N1 C12 1.348(3) . ? C19 C20 1.382(4) . ? C19 C18 1.391(3) . ? C19 H12 1.02(3) . ? C20 C21 1.387(3) . ? C20 H13 0.93(2) . ? C9 C8 1.373(3) . ? C9 C10 1.382(3) . ? C9 H7 0.97(2) . ? C16 C21 1.403(3) . ? C16 C17 1.409(3) . ? C16 C15 1.473(3) . ? C21 H14 1.00(3) . ? C14 C15 1.368(3) . ? C14 C13 1.468(3) . ? C2 C3 1.395(3) . ? C2 C7 1.396(3) . ? C2 C1 1.495(3) . ? C8 H6 0.91(2) . ? C10 C11 1.391(3) . ? C10 H8 0.93(3) . ? C6 C7 1.382(3) . ? C6 C5 1.389(3) . ? C6 H4 0.88(3) . ? C12 C11 1.397(3) . ? C18 C17 1.387(3) . ? C18 H11 0.91(2) . ? C11 H9 0.92(2) . ? C22 H18 0.96(2) . ? C22 H16 1.02(3) . ? C22 H17 0.98(2) . ? C3 C4 1.387(3) . ? C3 H2 0.93(2) . ? C5 C4 1.385(3) . ? C5 H3 0.97(3) . ? C7 H5 0.90(2) . ? 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 S1 O3 119.33(10) . . ? O4 S1 N3 108.02(10) . . ? O3 S1 N3 108.43(10) . . ? O4 S1 C17 108.60(10) . . ? O3 S1 C17 109.56(10) . . ? N3 S1 C17 101.40(10) . . ? C1 O2 H1 107(2) . . ? C15 O5 H15 108.5(19) . . ? C13 N2 C12 127.1(2) . . ? C13 N2 H10 114.1(15) . . ? C12 N2 H10 118.8(15) . . ? C14 N3 C22 115.20(18) . . ? C14 N3 S1 114.80(15) . . ? C22 N3 S1 116.73(16) . . ? C8 N1 C12 117.8(2) . . ? C20 C19 C18 120.4(2) . . ? C20 C19 H12 122.7(15) . . ? C18 C19 H12 116.9(15) . . ? C19 C20 C21 120.8(2) . . ? C19 C20 H13 123.2(15) . . ? C21 C20 H13 116.0(15) . . ? C8 C9 C10 117.8(2) . . ? C8 C9 H7 120.0(14) . . ? C10 C9 H7 122.2(14) . . ? C21 C16 C17 118.0(2) . . ? C21 C16 C15 120.7(2) . . ? C17 C16 C15 121.3(2) . . ? C20 C21 C16 120.2(2) . . ? C20 C21 H14 122.3(14) . . ? C16 C21 H14 117.4(14) . . ? C15 C14 N3 120.6(2) . . ? C15 C14 C13 120.8(2) . . ? N3 C14 C13 118.66(19) . . ? O5 C15 C14 123.3(2) . . ? O5 C15 C16 114.5(2) . . ? C14 C15 C16 122.2(2) . . ? O6 C13 N2 123.2(2) . . ? O6 C13 C14 120.4(2) . . ? N2 C13 C14 116.4(2) . . ? C3 C2 C7 120.2(2) . . ? C3 C2 C1 121.3(2) . . ? C7 C2 C1 118.5(2) . . ? N1 C8 C9 123.9(2) . . ? N1 C8 H6 113.9(15) . . ? C9 C8 H6 122.1(15) . . ? C9 C10 C11 120.1(2) . . ? C9 C10 H8 120.0(15) . . ? C11 C10 H8 119.8(15) . . ? C7 C6 C5 120.5(2) . . ? C7 C6 H4 120.1(18) . . ? C5 C6 H4 119.4(18) . . ? N1 C12 C11 122.3(2) . . ? N1 C12 N2 112.9(2) . . ? C11 C12 N2 124.8(2) . . ? O1 C1 O2 122.5(2) . . ? O1 C1 C2 122.6(2) . . ? O2 C1 C2 114.9(2) . . ? C17 C18 C19 119.0(2) . . ? C17 C18 H11 120.5(15) . . ? C19 C18 H11 120.5(15) . . ? C10 C11 C12 118.1(2) . . ? C10 C11 H9 119.3(15) . . ? C12 C11 H9 122.5(15) . . ? N3 C22 H18 113.5(14) . . ? N3 C22 H16 105.7(14) . . ? H18 C22 H16 105.2(19) . . ? N3 C22 H17 110.4(14) . . ? H18 C22 H17 110(2) . . ? H16 C22 H17 112(2) . . ? C4 C3 C2 118.5(2) . . ? C4 C3 H2 121.4(15) . . ? C2 C3 H2 120.1(15) . . ? C4 C5 C6 118.9(2) . . ? C4 C5 H3 121.8(15) . . ? C6 C5 H3 119.2(15) . . ? C18 C17 C16 121.6(2) . . ? C18 C17 S1 121.70(18) . . ? C16 C17 S1 116.69(17) . . ? C6 C7 C2 120.1(2) . . ? C6 C7 H5 118.7(16) . . ? C2 C7 H5 121.2(16) . . ? C5 C4 C3 121.8(2) . . ? C5 C4 Br1 118.63(18) . . ? C3 C4 Br1 119.53(18) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.32 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.625 _refine_diff_density_min -0.418 _refine_diff_density_rms 0.071 # Attachment 'PXN 3CLBA.cif' data_shelxl_PXN_3CLBA _database_code_depnum_ccdc_archive 'CCDC 890550' #TrackingRef 'PXN 3CLBA.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H13 N3 O4 S, C7 H5 Cl O2' _chemical_formula_sum 'C22 H18 Cl N3 O6 S' _chemical_formula_weight 487.90 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' Cl Cl 0.1484 0.1585 '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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.2160(5) _cell_length_b 10.9570(7) _cell_length_c 13.7261(9) _cell_angle_alpha 67.227(4) _cell_angle_beta 74.686(4) _cell_angle_gamma 68.598(4) _cell_volume 1049.85(12) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 27036 _cell_measurement_theta_min 1 _cell_measurement_theta_max 72.08 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.543 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 504 _exptl_absorpt_coefficient_mu 0.329 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8521 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'SADABS (Blessing, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'Bruker Apex II CCD' _diffrn_measurement_method 'CCD; rotation images' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 27036 _diffrn_reflns_av_R_equivalents 0.0786 _diffrn_reflns_av_sigmaI/netI 0.1044 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.63 _diffrn_reflns_theta_max 35.98 _reflns_number_total 9418 _reflns_number_gt 5619 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2 (2009)' _computing_cell_refinement 'Bruker APEX2 (2009)' _computing_data_reduction 'Bruker APEX2 (2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0343P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 9418 _refine_ls_number_parameters 370 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0851 _refine_ls_R_factor_gt 0.0454 _refine_ls_wR_factor_ref 0.1014 _refine_ls_wR_factor_gt 0.0928 _refine_ls_goodness_of_fit_ref 0.871 _refine_ls_restrained_S_all 0.871 _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 H13 H -0.348(2) 0.7784(17) 0.5515(14) 0.022(4) Uiso 1 1 d . . . H6 H 0.235(2) 0.6691(18) 0.2303(14) 0.022(4) Uiso 1 1 d . . . H7 H 0.100(2) 1.0262(17) 0.0902(14) 0.020(4) Uiso 1 1 d . . . H8 H -0.197(2) 1.1630(17) 0.0874(14) 0.018(4) Uiso 1 1 d . . . H2 H 1.024(2) 0.2335(17) 0.2397(13) 0.014(4) Uiso 1 1 d . . . H9 H -0.420(2) 1.0518(19) 0.1886(15) 0.032(5) Uiso 1 1 d . . . H16 H 0.426(2) 0.6280(18) 0.3616(14) 0.026(4) Uiso 1 1 d . . . H1 H 1.291(2) 0.2811(16) 0.1830(13) 0.015(4) Uiso 1 1 d . . . H17 H 0.494(2) 0.4625(19) 0.4040(15) 0.027(5) Uiso 1 1 d . . . H3 H 1.298(2) 0.5089(16) 0.0763(14) 0.020(4) Uiso 1 1 d . . . H4 H 1.031(2) 0.6858(17) 0.0391(14) 0.020(4) Uiso 1 1 d . . . H14 H 0.190(2) 0.6620(18) 0.5030(15) 0.030(5) Uiso 1 1 d . . . H18 H 0.632(2) 0.5456(17) 0.3655(14) 0.025(4) Uiso 1 1 d . . . H11 H -0.095(2) 1.0635(19) 0.3605(15) 0.031(5) Uiso 1 1 d . . . H12 H -0.357(2) 0.9998(18) 0.4427(14) 0.025(4) Uiso 1 1 d . . . H5 H 0.609(3) 0.852(2) 0.0263(17) 0.044(6) Uiso 1 1 d . . . H10 H -0.329(2) 0.8098(18) 0.2853(15) 0.027(5) Uiso 1 1 d . . . H15 H 0.064(3) 0.392(2) 0.6638(18) 0.048(6) Uiso 1 1 d . . . S1 S 0.66080(4) 0.39813(3) 0.21977(3) 0.01557(8) Uani 1 1 d . . . O3 O 0.72076(13) 0.79601(10) 0.02278(9) 0.0180(2) Uani 1 1 d . . . O4 O 0.38575(12) 0.89631(10) 0.07455(9) 0.0198(2) Uani 1 1 d . . . N2 N 0.22547(14) 0.75151(12) 0.19299(10) 0.0143(2) Uani 1 1 d . . . N1 N 0.53354(14) 0.54047(11) 0.24562(10) 0.0140(2) Uani 1 1 d . . . O2 O 0.66577(12) 0.28428(10) 0.31739(9) 0.0223(2) Uani 1 1 d . . . C4 C 0.86791(16) 0.43001(14) 0.17817(11) 0.0141(2) Uani 1 1 d . . . C5 C 0.86855(16) 0.56666(14) 0.11934(11) 0.0138(2) Uani 1 1 d . . . O1 O 0.60669(12) 0.39375(10) 0.13055(9) 0.0200(2) Uani 1 1 d . . . C9 C 0.54357(17) 0.66637(13) 0.16045(11) 0.0142(2) Uani 1 1 d . . . N3 N -0.07285(14) 0.78184(12) 0.24373(10) 0.0151(2) Uani 1 1 d . . . C10 C 0.37983(17) 0.78047(14) 0.13909(11) 0.0145(2) Uani 1 1 d . . . C7 C 0.70240(17) 0.67978(13) 0.10110(11) 0.0140(2) Uani 1 1 d . . . C11 C 0.05289(16) 0.84338(13) 0.18743(11) 0.0139(2) Uani 1 1 d . . . C6 C 1.03202(17) 0.59390(15) 0.08084(12) 0.0166(3) Uani 1 1 d . . . C13 C -0.16471(18) 1.06181(15) 0.13004(13) 0.0198(3) Uani 1 1 d . . . C12 C 0.01266(18) 0.98481(14) 0.13007(12) 0.0175(3) Uani 1 1 d . . . C3 C 1.02406(18) 0.32351(15) 0.20138(13) 0.0186(3) Uani 1 1 d . . . C8 C 0.52407(19) 0.54317(16) 0.35425(12) 0.0181(3) Uani 1 1 d . . . C1 C 1.18418(18) 0.35419(16) 0.16390(12) 0.0196(3) Uani 1 1 d . . . C14 C -0.29578(18) 0.99893(15) 0.18599(13) 0.0203(3) Uani 1 1 d . . . C2 C 1.18814(17) 0.48775(16) 0.10388(12) 0.0184(3) Uani 1 1 d . . . C15 C -0.24327(18) 0.85931(15) 0.24277(13) 0.0185(3) Uani 1 1 d . . . Cl1 Cl 0.26082(5) 0.91215(4) 0.36237(3) 0.02319(9) Uani 1 1 d . . . O5 O 0.07776(13) 0.46749(11) 0.62169(9) 0.0203(2) Uani 1 1 d . . . C21 C -0.08294(17) 0.69980(14) 0.53870(11) 0.0144(2) Uani 1 1 d . . . O6 O -0.21654(13) 0.52423(10) 0.65080(9) 0.0227(2) Uani 1 1 d . . . C22 C -0.08180(17) 0.55613(14) 0.60948(11) 0.0152(3) Uani 1 1 d . . . C18 C -0.09440(19) 0.96926(15) 0.40708(13) 0.0202(3) Uani 1 1 d . . . C16 C 0.07491(17) 0.73316(14) 0.49075(11) 0.0153(3) Uani 1 1 d . . . C17 C 0.06566(17) 0.86818(14) 0.42498(11) 0.0162(3) Uani 1 1 d . . . C20 C -0.24555(18) 0.80045(15) 0.52099(13) 0.0187(3) Uani 1 1 d . . . C19 C -0.25027(19) 0.93447(15) 0.45533(13) 0.0216(3) 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 0.01110(14) 0.01052(15) 0.02092(19) -0.00214(13) -0.00123(12) -0.00248(11) O3 0.0150(5) 0.0124(5) 0.0196(6) 0.0001(4) 0.0006(4) -0.0041(4) O4 0.0143(4) 0.0131(5) 0.0232(6) 0.0005(4) -0.0006(4) -0.0025(4) N2 0.0116(5) 0.0090(5) 0.0178(6) -0.0005(5) -0.0022(4) -0.0019(4) N1 0.0115(5) 0.0111(5) 0.0143(6) -0.0011(4) -0.0002(4) -0.0018(4) O2 0.0155(5) 0.0124(5) 0.0270(6) 0.0033(4) -0.0007(4) -0.0029(4) C4 0.0106(5) 0.0141(6) 0.0151(7) -0.0036(5) 0.0004(5) -0.0034(5) C5 0.0120(5) 0.0144(6) 0.0140(6) -0.0050(5) -0.0006(5) -0.0032(5) O1 0.0160(5) 0.0176(5) 0.0278(6) -0.0089(5) -0.0026(4) -0.0053(4) C9 0.0129(6) 0.0109(6) 0.0154(7) -0.0015(5) -0.0018(5) -0.0028(5) N3 0.0126(5) 0.0134(5) 0.0183(6) -0.0044(5) -0.0022(4) -0.0037(4) C10 0.0137(6) 0.0122(6) 0.0151(7) -0.0030(5) -0.0015(5) -0.0030(5) C7 0.0152(6) 0.0107(6) 0.0151(7) -0.0021(5) -0.0028(5) -0.0043(5) C11 0.0119(5) 0.0123(6) 0.0161(7) -0.0043(5) -0.0030(5) -0.0016(5) C6 0.0146(6) 0.0167(7) 0.0180(7) -0.0052(6) -0.0007(5) -0.0056(5) C13 0.0173(6) 0.0142(7) 0.0204(8) -0.0018(6) -0.0026(5) -0.0003(5) C12 0.0150(6) 0.0136(6) 0.0192(7) -0.0022(6) -0.0008(5) -0.0034(5) C3 0.0141(6) 0.0145(7) 0.0220(8) -0.0031(6) -0.0031(5) -0.0013(5) C8 0.0164(6) 0.0188(7) 0.0165(7) -0.0029(6) -0.0026(5) -0.0053(5) C1 0.0113(6) 0.0226(7) 0.0206(8) -0.0067(6) -0.0022(5) -0.0008(5) C14 0.0123(6) 0.0182(7) 0.0260(8) -0.0063(6) -0.0043(6) 0.0007(5) C2 0.0113(6) 0.0249(7) 0.0194(7) -0.0084(6) -0.0006(5) -0.0054(5) C15 0.0138(6) 0.0175(7) 0.0225(8) -0.0058(6) -0.0006(5) -0.0049(5) Cl1 0.02151(17) 0.02020(18) 0.0275(2) -0.00633(15) 0.00368(14) -0.01222(14) O5 0.0136(4) 0.0132(5) 0.0281(6) 0.0002(5) -0.0033(4) -0.0046(4) C21 0.0147(6) 0.0139(6) 0.0142(7) -0.0039(5) -0.0021(5) -0.0044(5) O6 0.0144(5) 0.0174(5) 0.0277(6) 0.0022(5) -0.0015(4) -0.0064(4) C22 0.0136(6) 0.0149(6) 0.0164(7) -0.0040(5) -0.0032(5) -0.0039(5) C18 0.0237(7) 0.0133(7) 0.0205(8) -0.0038(6) -0.0007(6) -0.0057(5) C16 0.0142(6) 0.0146(6) 0.0162(7) -0.0046(5) -0.0010(5) -0.0045(5) C17 0.0174(6) 0.0168(7) 0.0155(7) -0.0051(5) 0.0013(5) -0.0090(5) C20 0.0135(6) 0.0181(7) 0.0215(8) -0.0046(6) -0.0003(5) -0.0050(5) C19 0.0173(7) 0.0161(7) 0.0239(8) -0.0036(6) -0.0019(6) -0.0004(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_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O1 1.4311(10) . ? S1 O2 1.4322(11) . ? S1 N1 1.6413(11) . ? S1 C4 1.7634(13) . ? O3 C7 1.3398(17) . ? O4 C10 1.2450(17) . ? N2 C10 1.3685(17) . ? N2 C11 1.4091(16) . ? N1 C9 1.4353(18) . ? N1 C8 1.4838(18) . ? C4 C3 1.3945(18) . ? C4 C5 1.4006(19) . ? C5 C6 1.4028(18) . ? C5 C7 1.4724(18) . ? C9 C7 1.3689(19) . ? C9 C10 1.4683(18) . ? N3 C11 1.3425(17) . ? N3 C15 1.3472(17) . ? C11 C12 1.3963(19) . ? C6 C2 1.3924(19) . ? C13 C14 1.385(2) . ? C13 C12 1.3922(19) . ? C3 C1 1.3927(19) . ? C1 C2 1.381(2) . ? C14 C15 1.381(2) . ? Cl1 C17 1.7484(13) . ? O5 C22 1.3232(16) . ? C21 C20 1.3960(19) . ? C21 C16 1.3992(18) . ? C21 C22 1.4941(19) . ? O6 C22 1.2110(16) . ? C18 C17 1.383(2) . ? C18 C19 1.392(2) . ? C16 C17 1.3891(19) . ? C20 C19 1.387(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 S1 O2 119.26(6) . . ? O1 S1 N1 108.07(6) . . ? O2 S1 N1 108.40(6) . . ? O1 S1 C4 108.45(6) . . ? O2 S1 C4 109.61(6) . . ? N1 S1 C4 101.59(6) . . ? C10 N2 C11 127.23(12) . . ? C9 N1 C8 115.23(11) . . ? C9 N1 S1 114.73(9) . . ? C8 N1 S1 116.49(9) . . ? C3 C4 C5 121.58(12) . . ? C3 C4 S1 121.46(11) . . ? C5 C4 S1 116.96(9) . . ? C4 C5 C6 118.20(12) . . ? C4 C5 C7 121.12(11) . . ? C6 C5 C7 120.66(12) . . ? C7 C9 N1 120.65(11) . . ? C7 C9 C10 120.90(12) . . ? N1 C9 C10 118.44(11) . . ? C11 N3 C15 118.52(12) . . ? O4 C10 N2 123.26(12) . . ? O4 C10 C9 120.16(12) . . ? N2 C10 C9 116.58(12) . . ? O3 C7 C9 123.36(12) . . ? O3 C7 C5 114.37(11) . . ? C9 C7 C5 122.26(12) . . ? N3 C11 C12 122.18(12) . . ? N3 C11 N2 113.32(11) . . ? C12 C11 N2 124.50(12) . . ? C2 C6 C5 120.31(13) . . ? C14 C13 C12 120.47(13) . . ? C13 C12 C11 117.89(13) . . ? C1 C3 C4 118.91(13) . . ? C2 C1 C3 120.47(13) . . ? C15 C14 C13 117.52(13) . . ? C1 C2 C6 120.50(13) . . ? N3 C15 C14 123.38(13) . . ? C20 C21 C16 120.53(13) . . ? C20 C21 C22 118.46(12) . . ? C16 C21 C22 121.00(11) . . ? O6 C22 O5 123.32(13) . . ? O6 C22 C21 122.27(12) . . ? O5 C22 C21 114.41(11) . . ? C17 C18 C19 119.15(14) . . ? C17 C16 C21 118.44(12) . . ? C18 C17 C16 121.73(13) . . ? C18 C17 Cl1 118.85(11) . . ? C16 C17 Cl1 119.43(10) . . ? C19 C20 C21 119.61(13) . . ? C20 C19 C18 120.54(13) . . ? _diffrn_measured_fraction_theta_max 0.948 _diffrn_reflns_theta_full 35.98 _diffrn_measured_fraction_theta_full 0.948 _refine_diff_density_max 0.694 _refine_diff_density_min -0.441 _refine_diff_density_rms 0.081 # Attachment 'PXN 3FBA.cif' data_shelxl_PXN_3FBA _database_code_depnum_ccdc_archive 'CCDC 890551' #TrackingRef 'PXN 3FBA.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H18 F N3 O6 S' _chemical_formula_weight 471.45 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' 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.4670(6) _cell_length_b 11.1895(9) _cell_length_c 12.2950(9) _cell_angle_alpha 114.729(4) _cell_angle_beta 96.555(4) _cell_angle_gamma 98.491(4) _cell_volume 1026.17(13) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 27140 _cell_measurement_theta_min 1 _cell_measurement_theta_max 59.08 _exptl_crystal_description plates _exptl_crystal_colour colourless _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.526 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 488 _exptl_absorpt_coefficient_mu 0.215 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.08376 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'SADABS (Blessing, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'Bruker Apex II CCD' _diffrn_measurement_method 'CCD; rotation images' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 27127 _diffrn_reflns_av_R_equivalents 0.0883 _diffrn_reflns_av_sigmaI/netI 0.0655 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 29.50 _reflns_number_total 5635 _reflns_number_gt 3967 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2 (2009)' _computing_cell_refinement 'Bruker APEX2 (2009)' _computing_data_reduction 'Bruker APEX2 (2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0513P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5635 _refine_ls_number_parameters 370 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0682 _refine_ls_R_factor_gt 0.0417 _refine_ls_wR_factor_ref 0.1025 _refine_ls_wR_factor_gt 0.0937 _refine_ls_goodness_of_fit_ref 0.947 _refine_ls_restrained_S_all 0.947 _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 O5 O 0.70210(14) 0.96991(11) 1.06118(11) 0.0201(2) Uani 1 1 d . . . O3 O 0.31823(13) 0.77501(11) 0.73883(10) 0.0206(3) Uani 1 1 d . . . O6 O 0.46538(13) 0.95208(11) 1.17355(10) 0.0223(3) Uani 1 1 d . . . O4 O 0.31965(14) 0.53220(12) 0.64630(10) 0.0249(3) Uani 1 1 d . . . C22 C 0.3982(2) 0.54440(17) 0.88557(17) 0.0217(4) Uani 1 1 d . . . H6 H 0.513(2) 0.5398(17) 0.8960(15) 0.018(4) Uiso 1 1 d . . . H10 H 0.281(2) 0.9937(19) 1.2910(17) 0.027(5) Uiso 1 1 d . . . H9 H 0.183(2) 0.726(2) 0.9987(19) 0.033(6) Uiso 1 1 d . . . H4 H 0.601(2) 0.5871(19) 0.5723(18) 0.028(5) Uiso 1 1 d . . . H1 H 0.893(2) 0.643(2) 0.5943(19) 0.036(5) Uiso 1 1 d . . . H8 H 0.333(2) 0.4656(17) 0.8156(15) 0.013(4) Uiso 1 1 d . . . H2 H 1.035(2) 0.790(2) 0.7816(18) 0.032(5) Uiso 1 1 d . . . H13 H -0.237(2) 0.7400(18) 1.1554(16) 0.024(5) Uiso 1 1 d . . . H12 H -0.175(2) 0.9271(18) 1.3510(17) 0.027(5) Uiso 1 1 d . . . H3 H 0.923(2) 0.8916(18) 0.9580(16) 0.019(4) Uiso 1 1 d . . . H5 H 0.647(3) 0.988(2) 1.119(2) 0.051(7) Uiso 1 1 d . . . H11 H 0.095(2) 1.058(2) 1.4240(18) 0.030(5) Uiso 1 1 d . . . H7 H 0.353(2) 0.5468(19) 0.9578(18) 0.033(5) Uiso 1 1 d . . . H15 H 1.004(2) 0.3784(18) 0.6311(16) 0.023(5) Uiso 1 1 d . . . H18 H 0.868(2) 0.2002(17) 0.4386(17) 0.020(4) Uiso 1 1 d . . . H16 H 0.595(2) 0.3463(17) 0.7637(16) 0.020(4) Uiso 1 1 d . . . H17 H 0.596(2) 0.1035(18) 0.4111(17) 0.023(5) Uiso 1 1 d . . . H14 H 0.881(3) 0.613(2) 0.981(2) 0.047(6) Uiso 1 1 d . . . S1 S 0.38610(5) 0.66612(4) 0.74020(4) 0.01757(11) Uani 1 1 d . . . N1 N 0.37758(15) 0.66739(12) 0.87335(11) 0.0160(3) Uani 1 1 d . . . N3 N -0.02447(16) 0.76047(13) 1.11545(12) 0.0175(3) Uani 1 1 d . . . N2 N 0.22918(16) 0.79217(14) 1.06821(13) 0.0169(3) Uani 1 1 d . . . C11 C 0.59830(18) 0.70611(15) 0.74970(15) 0.0179(3) Uani 1 1 d . . . C16 C 0.38740(18) 0.85164(15) 1.07989(14) 0.0168(3) Uani 1 1 d . . . C8 C 0.46463(19) 0.79163(15) 0.97506(14) 0.0161(3) Uani 1 1 d . . . C18 C 0.1781(2) 0.94683(16) 1.26883(15) 0.0194(3) Uani 1 1 d . . . C13 C 0.86064(19) 0.83150(16) 0.87566(16) 0.0194(3) Uani 1 1 d . . . C9 C 0.61447(18) 0.85344(15) 0.97108(14) 0.0161(3) Uani 1 1 d . . . C17 C 0.12821(19) 0.83570(15) 1.15393(14) 0.0163(3) Uani 1 1 d . . . C20 C -0.0934(2) 0.90476(17) 1.30339(16) 0.0223(4) Uani 1 1 d . . . C10 C 0.6695(2) 0.64874(17) 0.64936(16) 0.0238(4) Uani 1 1 d . . . C19 C 0.0652(2) 0.98016(17) 1.34299(16) 0.0225(4) Uani 1 1 d . . . C12 C 0.69183(18) 0.79746(15) 0.86500(14) 0.0164(3) Uani 1 1 d . . . C21 C -0.1315(2) 0.79580(16) 1.18927(15) 0.0198(3) Uani 1 1 d . . . C14 C 0.9322(2) 0.77459(17) 0.77616(16) 0.0222(4) Uani 1 1 d . . . C15 C 0.8379(2) 0.68332(17) 0.66308(17) 0.0251(4) Uani 1 1 d . . . F1 F 0.41649(12) 0.15851(11) 0.57259(10) 0.0350(3) Uani 1 1 d . . . O2 O 0.81406(14) 0.53704(12) 0.91824(11) 0.0228(3) Uani 1 1 d . . . O1 O 1.04878(13) 0.54100(12) 0.85224(11) 0.0249(3) Uani 1 1 d . . . C4 C 0.81464(19) 0.37824(15) 0.71633(14) 0.0171(3) Uani 1 1 d . . . C7 C 0.90455(18) 0.49239(15) 0.83487(14) 0.0173(3) Uani 1 1 d . . . C3 C 0.8961(2) 0.33490(16) 0.61960(15) 0.0206(3) Uani 1 1 d . . . C1 C 0.6522(2) 0.17237(17) 0.49016(16) 0.0231(4) Uani 1 1 d . . . C2 C 0.8138(2) 0.23247(17) 0.50682(16) 0.0229(4) Uani 1 1 d . . . C5 C 0.6521(2) 0.31806(16) 0.70121(15) 0.0199(3) Uani 1 1 d . . . C6 C 0.57531(19) 0.21658(16) 0.58787(16) 0.0222(4) 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 O5 0.0180(6) 0.0193(6) 0.0152(6) 0.0029(5) 0.0008(5) -0.0019(4) O3 0.0182(6) 0.0253(6) 0.0158(6) 0.0084(5) 0.0007(5) 0.0020(5) O6 0.0202(6) 0.0228(6) 0.0141(6) 0.0020(5) 0.0022(5) -0.0038(5) O4 0.0218(6) 0.0238(6) 0.0163(6) -0.0002(5) 0.0036(5) -0.0045(5) C22 0.0204(9) 0.0169(8) 0.0263(10) 0.0088(7) 0.0044(7) 0.0025(7) S1 0.01455(19) 0.0189(2) 0.0129(2) 0.00258(15) 0.00247(14) -0.00081(14) N1 0.0169(6) 0.0138(6) 0.0131(7) 0.0033(5) 0.0027(5) 0.0000(5) N3 0.0176(7) 0.0176(6) 0.0159(7) 0.0071(6) 0.0025(5) 0.0017(5) N2 0.0169(7) 0.0164(7) 0.0122(7) 0.0025(6) 0.0023(5) 0.0004(5) C11 0.0141(7) 0.0177(8) 0.0194(8) 0.0067(7) 0.0033(6) 0.0006(6) C16 0.0171(8) 0.0177(7) 0.0149(8) 0.0076(6) 0.0014(6) 0.0015(6) C8 0.0176(8) 0.0155(7) 0.0122(7) 0.0041(6) 0.0013(6) 0.0021(6) C18 0.0192(8) 0.0192(8) 0.0153(8) 0.0050(7) 0.0019(6) 0.0003(6) C13 0.0170(8) 0.0189(8) 0.0211(9) 0.0097(7) 0.0005(7) 0.0008(6) C9 0.0162(8) 0.0154(7) 0.0141(8) 0.0057(6) -0.0012(6) 0.0016(6) C17 0.0180(8) 0.0177(7) 0.0139(8) 0.0077(6) 0.0025(6) 0.0041(6) C20 0.0242(9) 0.0253(9) 0.0196(9) 0.0099(7) 0.0098(7) 0.0080(7) C10 0.0237(9) 0.0215(8) 0.0192(9) 0.0034(7) 0.0070(7) -0.0005(7) C19 0.0269(9) 0.0206(8) 0.0147(8) 0.0043(7) 0.0023(7) 0.0024(7) C12 0.0162(8) 0.0141(7) 0.0177(8) 0.0064(6) 0.0032(6) 0.0015(6) C21 0.0184(8) 0.0206(8) 0.0197(9) 0.0091(7) 0.0031(7) 0.0016(7) C14 0.0155(8) 0.0229(8) 0.0301(10) 0.0129(8) 0.0072(7) 0.0037(7) C15 0.0241(9) 0.0217(8) 0.0277(10) 0.0076(8) 0.0131(7) 0.0036(7) F1 0.0208(5) 0.0376(6) 0.0301(6) 0.0056(5) 0.0011(4) -0.0095(4) O2 0.0185(6) 0.0234(6) 0.0161(6) 0.0012(5) 0.0035(5) -0.0028(5) O1 0.0173(6) 0.0251(6) 0.0222(6) 0.0031(5) 0.0023(5) -0.0005(5) C4 0.0177(8) 0.0149(7) 0.0171(8) 0.0069(6) -0.0001(6) 0.0021(6) C7 0.0169(8) 0.0165(7) 0.0179(8) 0.0080(6) 0.0022(6) 0.0022(6) C3 0.0181(8) 0.0216(8) 0.0198(9) 0.0084(7) 0.0017(7) 0.0016(7) C1 0.0265(9) 0.0196(8) 0.0162(9) 0.0042(7) -0.0022(7) 0.0009(7) C2 0.0254(9) 0.0237(9) 0.0169(9) 0.0068(7) 0.0036(7) 0.0043(7) C5 0.0191(8) 0.0196(8) 0.0190(8) 0.0069(7) 0.0041(7) 0.0026(6) C6 0.0169(8) 0.0203(8) 0.0236(9) 0.0080(7) -0.0015(7) -0.0033(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 O5 C9 1.3398(18) . ? O5 H5 0.87(2) . ? O3 S1 1.4273(12) . ? O6 C16 1.2448(18) . ? O4 S1 1.4319(12) . ? C22 N1 1.478(2) . ? C22 H6 0.977(17) . ? C22 H8 0.966(17) . ? C22 H7 1.00(2) . ? S1 N1 1.6411(13) . ? S1 C11 1.7644(16) . ? N1 C8 1.4395(19) . ? N3 C21 1.339(2) . ? N3 C17 1.345(2) . ? N2 C16 1.368(2) . ? N2 C17 1.406(2) . ? N2 H9 0.86(2) . ? C11 C10 1.385(2) . ? C11 C12 1.405(2) . ? C16 C8 1.462(2) . ? C8 C9 1.369(2) . ? C18 C19 1.380(2) . ? C18 C17 1.400(2) . ? C18 H10 0.89(2) . ? C13 C14 1.379(2) . ? C13 C12 1.400(2) . ? C13 H3 0.979(18) . ? C9 C12 1.468(2) . ? C20 C21 1.381(2) . ? C20 C19 1.388(2) . ? C20 H12 0.950(19) . ? C10 C15 1.393(2) . ? C10 H4 0.959(19) . ? C19 H11 0.98(2) . ? C21 H13 0.949(19) . ? C14 C15 1.389(3) . ? C14 H2 0.85(2) . ? C15 H1 0.98(2) . ? F1 C6 1.3594(18) . ? O2 C7 1.3233(19) . ? O2 H14 0.92(2) . ? O1 C7 1.2165(18) . ? C4 C3 1.389(2) . ? C4 C5 1.395(2) . ? C4 C7 1.496(2) . ? C3 C2 1.391(2) . ? C3 H15 0.934(18) . ? C1 C6 1.374(2) . ? C1 C2 1.385(2) . ? C1 H17 0.962(18) . ? C2 H18 0.964(19) . ? C5 C6 1.380(2) . ? C5 H16 0.921(18) . ? 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 O5 H5 104.3(16) . . ? N1 C22 H6 110.9(10) . . ? N1 C22 H8 110.0(9) . . ? H6 C22 H8 111.3(14) . . ? N1 C22 H7 107.7(11) . . ? H6 C22 H7 110.7(15) . . ? H8 C22 H7 106.2(15) . . ? O3 S1 O4 119.55(7) . . ? O3 S1 N1 106.92(7) . . ? O4 S1 N1 108.79(7) . . ? O3 S1 C11 109.00(7) . . ? O4 S1 C11 109.61(7) . . ? N1 S1 C11 101.42(7) . . ? C8 N1 C22 114.66(12) . . ? C8 N1 S1 113.46(10) . . ? C22 N1 S1 117.20(11) . . ? C21 N3 C17 118.32(14) . . ? C16 N2 C17 126.78(14) . . ? C16 N2 H9 117.0(14) . . ? C17 N2 H9 115.9(14) . . ? C10 C11 C12 121.65(15) . . ? C10 C11 S1 121.85(13) . . ? C12 C11 S1 116.49(12) . . ? O6 C16 N2 123.33(14) . . ? O6 C16 C8 119.98(14) . . ? N2 C16 C8 116.69(14) . . ? C9 C8 N1 120.14(14) . . ? C9 C8 C16 121.20(14) . . ? N1 C8 C16 118.63(13) . . ? C19 C18 C17 118.29(16) . . ? C19 C18 H10 122.6(13) . . ? C17 C18 H10 119.1(13) . . ? C14 C13 C12 120.64(16) . . ? C14 C13 H3 123.2(10) . . ? C12 C13 H3 116.0(10) . . ? O5 C9 C8 123.73(14) . . ? O5 C9 C12 114.12(13) . . ? C8 C9 C12 122.14(14) . . ? N3 C17 C18 121.96(15) . . ? N3 C17 N2 113.69(13) . . ? C18 C17 N2 124.35(14) . . ? C21 C20 C19 117.53(16) . . ? C21 C20 H12 120.2(12) . . ? C19 C20 H12 122.3(12) . . ? C11 C10 C15 119.10(16) . . ? C11 C10 H4 118.9(12) . . ? C15 C10 H4 122.0(11) . . ? C18 C19 C20 120.25(16) . . ? C18 C19 H11 120.7(12) . . ? C20 C19 H11 119.0(11) . . ? C13 C12 C11 117.94(15) . . ? C13 C12 C9 121.28(14) . . ? C11 C12 C9 120.77(14) . . ? N3 C21 C20 123.63(15) . . ? N3 C21 H13 113.8(11) . . ? C20 C21 H13 122.6(11) . . ? C13 C14 C15 120.63(16) . . ? C13 C14 H2 122.2(14) . . ? C15 C14 H2 117.1(14) . . ? C14 C15 C10 120.02(16) . . ? C14 C15 H1 118.7(12) . . ? C10 C15 H1 121.2(12) . . ? C7 O2 H14 104.7(14) . . ? C3 C4 C5 120.28(15) . . ? C3 C4 C7 118.25(14) . . ? C5 C4 C7 121.45(14) . . ? O1 C7 O2 122.95(15) . . ? O1 C7 C4 122.47(14) . . ? O2 C7 C4 114.58(13) . . ? C4 C3 C2 119.58(16) . . ? C4 C3 H15 118.8(11) . . ? C2 C3 H15 121.5(11) . . ? C6 C1 C2 118.24(16) . . ? C6 C1 H17 121.7(11) . . ? C2 C1 H17 120.0(11) . . ? C1 C2 C3 120.81(16) . . ? C1 C2 H18 118.2(11) . . ? C3 C2 H18 121.0(11) . . ? C6 C5 C4 118.19(15) . . ? C6 C5 H16 120.1(11) . . ? C4 C5 H16 121.7(11) . . ? F1 C6 C1 118.79(15) . . ? F1 C6 C5 118.32(15) . . ? C1 C6 C5 122.88(15) . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.624 _refine_diff_density_min -0.461 _refine_diff_density_rms 0.064 # Attachment 'PXN 3NBA.cif' data_shelxl_PXN_3NBA _database_code_depnum_ccdc_archive 'CCDC 890552' #TrackingRef 'PXN 3NBA.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H13 N3 O4 S, C7 H5 N O4' _chemical_formula_sum 'C22 H18 N4 O8 S' _chemical_formula_weight 498.46 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.2304(4) _cell_length_b 10.8476(6) _cell_length_c 13.7358(7) _cell_angle_alpha 68.2669(28) _cell_angle_beta 75.0863(28) _cell_angle_gamma 69.1073(27) _cell_volume 1053.11(9) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 27710 _cell_measurement_theta_min 1 _cell_measurement_theta_max 55.50 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.572 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 516 _exptl_absorpt_coefficient_mu 0.215 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8485 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'SADABS (Blessing, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'Bruker Apex II CCD' _diffrn_measurement_method 'CCD; rotation images' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 27710 _diffrn_reflns_av_R_equivalents 0.0850 _diffrn_reflns_av_sigmaI/netI 0.0652 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.61 _diffrn_reflns_theta_max 27.67 _reflns_number_total 4908 _reflns_number_gt 3448 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2 (2009)' _computing_cell_refinement 'Bruker APEX2 (2009)' _computing_data_reduction 'Bruker APEX2 (2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0502P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4908 _refine_ls_number_parameters 388 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0620 _refine_ls_R_factor_gt 0.0380 _refine_ls_wR_factor_ref 0.0928 _refine_ls_wR_factor_gt 0.0848 _refine_ls_goodness_of_fit_ref 0.875 _refine_ls_restrained_S_all 0.875 _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 H17 H 0.412(2) 0.560(2) 0.3657(16) 0.025(5) Uiso 1 1 d . . . H14 H 0.683(2) 0.167(2) 0.5116(15) 0.023(5) Uiso 1 1 d . . . H16 H 0.152(3) 0.504(2) 0.4379(15) 0.026(5) Uiso 1 1 d . . . H15 H 0.156(3) 0.277(2) 0.5495(16) 0.026(5) Uiso 1 1 d . . . H12 H 0.560(3) -0.113(2) 0.6661(18) 0.038(7) Uiso 1 1 d . . . H4 H 1.521(2) -0.268(2) 0.2291(15) 0.018(5) Uiso 1 1 d . . . H1 H 1.536(2) 0.1866(19) 0.0461(14) 0.013(5) Uiso 1 1 d . . . H2 H 1.794(2) 0.0136(19) 0.0813(14) 0.019(5) Uiso 1 1 d . . . H6 H 1.013(2) -0.051(2) 0.4025(16) 0.027(5) Uiso 1 1 d . . . H5 H 1.142(2) 0.049(2) 0.3612(15) 0.023(5) Uiso 1 1 d . . . H10 H 0.307(2) 0.659(2) 0.0910(15) 0.021(5) Uiso 1 1 d . . . H13 H 0.178(2) 0.3061(18) 0.2894(13) 0.011(4) Uiso 1 1 d . . . H3 H 1.786(3) -0.217(2) 0.1757(16) 0.029(6) Uiso 1 1 d . . . H9 H 0.607(2) 0.5275(19) 0.0953(14) 0.017(5) Uiso 1 1 d . . . H8 H 0.737(2) 0.168(2) 0.2387(15) 0.021(5) Uiso 1 1 d . . . H11 H 0.087(3) 0.543(2) 0.1910(16) 0.031(6) Uiso 1 1 d . . . H18 H 1.116(3) 0.359(2) 0.0280(18) 0.046(7) Uiso 1 1 d . . . H7 H 0.934(3) 0.115(2) 0.3635(16) 0.028(5) Uiso 1 1 d . . . O8 O 0.73228(16) 0.51119(14) 0.31459(11) 0.0298(3) Uani 1 1 d . . . O6 O 0.57261(15) -0.03200(14) 0.62399(11) 0.0215(3) Uani 1 1 d . . . O5 O 0.27946(15) 0.02534(13) 0.64834(10) 0.0248(3) Uani 1 1 d . . . O7 O 0.87072(15) 0.31899(13) 0.42127(10) 0.0236(3) Uani 1 1 d . . . N5 N 0.73541(18) 0.40166(16) 0.38589(12) 0.0190(3) Uani 1 1 d . . . C16 C 0.4154(2) 0.05711(18) 0.60961(14) 0.0162(4) Uani 1 1 d . . . C20 C 0.4120(2) 0.4686(2) 0.40891(14) 0.0175(4) Uani 1 1 d . . . C19 C 0.5684(2) 0.36620(18) 0.43280(13) 0.0160(4) Uani 1 1 d . . . C17 C 0.4171(2) 0.19993(18) 0.54130(13) 0.0159(4) Uani 1 1 d . . . C18 C 0.5754(2) 0.23308(19) 0.49819(14) 0.0160(4) Uani 1 1 d . . . C22 C 0.2578(2) 0.3013(2) 0.51949(15) 0.0186(4) Uani 1 1 d . . . C21 C 0.2548(2) 0.4342(2) 0.45425(15) 0.0204(4) Uani 1 1 d . . . C15 C 0.2614(2) 0.35659(19) 0.24675(14) 0.0181(4) Uani 1 1 d . . . S1 S 1.16235(5) -0.10376(5) 0.21286(4) 0.01583(12) Uani 1 1 d . . . O3 O 1.22080(15) 0.29670(13) 0.02719(10) 0.0194(3) Uani 1 1 d . . . O4 O 0.88778(15) 0.39436(13) 0.07836(10) 0.0219(3) Uani 1 1 d . . . O2 O 1.16855(15) -0.22046(13) 0.30695(10) 0.0212(3) Uani 1 1 d . . . O1 O 1.10639(14) -0.10487(13) 0.12279(10) 0.0194(3) Uani 1 1 d . . . N1 N 1.03608(17) 0.03642(15) 0.24379(11) 0.0152(3) Uani 1 1 d . . . N3 N 0.72916(17) 0.25079(16) 0.19825(12) 0.0160(3) Uani 1 1 d . . . N4 N 0.43144(17) 0.28001(15) 0.24829(11) 0.0156(3) Uani 1 1 d . . . C1 C 1.3682(2) -0.07042(18) 0.17352(13) 0.0149(4) Uani 1 1 d . . . C10 C 0.8826(2) 0.27908(18) 0.14235(14) 0.0162(4) Uani 1 1 d . . . C2 C 1.3687(2) 0.06724(18) 0.11916(13) 0.0147(4) Uani 1 1 d . . . C7 C 1.0456(2) 0.16442(18) 0.16166(14) 0.0154(4) Uani 1 1 d . . . C8 C 1.2035(2) 0.17978(18) 0.10283(13) 0.0149(4) Uani 1 1 d . . . C6 C 1.5234(2) -0.1770(2) 0.19443(14) 0.0183(4) Uani 1 1 d . . . C12 C 0.5164(2) 0.48209(19) 0.13241(14) 0.0185(4) Uani 1 1 d . . . C9 C 1.0326(2) 0.0356(2) 0.35274(14) 0.0186(4) Uani 1 1 d . . . C11 C 0.5564(2) 0.34174(18) 0.19170(13) 0.0151(4) Uani 1 1 d . . . C3 C 1.5311(2) 0.0954(2) 0.08362(14) 0.0167(4) Uani 1 1 d . . . C5 C 1.6825(2) -0.1452(2) 0.16021(14) 0.0197(4) Uani 1 1 d . . . C4 C 1.6866(2) -0.0109(2) 0.10476(14) 0.0190(4) Uani 1 1 d . . . C14 C 0.2097(2) 0.4946(2) 0.18896(15) 0.0197(4) Uani 1 1 d . . . C13 C 0.3398(2) 0.5577(2) 0.13172(15) 0.0204(4) 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 O8 0.0229(7) 0.0219(8) 0.0338(8) 0.0062(7) -0.0028(6) -0.0105(6) O6 0.0135(6) 0.0151(7) 0.0290(8) 0.0012(6) -0.0033(5) -0.0044(5) O5 0.0139(6) 0.0221(7) 0.0301(8) 0.0024(6) -0.0019(5) -0.0074(5) O7 0.0133(6) 0.0215(7) 0.0308(8) -0.0040(6) -0.0030(5) -0.0033(5) N5 0.0180(7) 0.0166(8) 0.0211(8) -0.0043(7) -0.0007(6) -0.0067(6) C16 0.0136(8) 0.0186(10) 0.0160(9) -0.0052(8) -0.0018(7) -0.0045(7) C20 0.0189(9) 0.0141(10) 0.0171(9) -0.0029(8) -0.0023(7) -0.0043(7) C19 0.0141(8) 0.0195(10) 0.0152(9) -0.0061(8) -0.0002(7) -0.0061(7) C17 0.0148(8) 0.0178(10) 0.0150(9) -0.0054(7) -0.0013(7) -0.0049(7) C18 0.0131(8) 0.0172(10) 0.0166(9) -0.0052(8) -0.0028(7) -0.0026(7) C22 0.0126(8) 0.0215(10) 0.0204(9) -0.0060(8) -0.0003(7) -0.0054(7) C21 0.0148(9) 0.0206(10) 0.0220(10) -0.0067(8) -0.0027(7) -0.0005(7) C15 0.0124(8) 0.0199(10) 0.0213(10) -0.0077(8) -0.0010(7) -0.0037(7) S1 0.01044(19) 0.0127(2) 0.0206(2) -0.00266(18) -0.00125(16) -0.00234(16) O3 0.0132(6) 0.0150(7) 0.0223(7) -0.0012(6) 0.0010(5) -0.0026(5) O4 0.0144(6) 0.0155(7) 0.0265(7) 0.0008(6) -0.0001(5) -0.0031(5) O2 0.0161(6) 0.0150(7) 0.0241(7) 0.0003(6) -0.0009(5) -0.0028(5) O1 0.0151(6) 0.0197(7) 0.0236(7) -0.0073(6) -0.0028(5) -0.0048(5) N1 0.0108(6) 0.0137(8) 0.0156(7) -0.0012(6) 0.0004(5) -0.0022(6) N3 0.0105(7) 0.0131(8) 0.0196(8) -0.0012(7) -0.0016(6) -0.0021(6) N4 0.0116(7) 0.0172(8) 0.0177(8) -0.0058(6) -0.0017(6) -0.0038(6) C1 0.0107(8) 0.0170(9) 0.0148(9) -0.0045(7) -0.0006(6) -0.0027(7) C10 0.0139(8) 0.0164(10) 0.0173(9) -0.0049(8) -0.0011(7) -0.0045(7) C2 0.0118(8) 0.0174(9) 0.0139(9) -0.0051(7) -0.0007(6) -0.0036(7) C7 0.0128(8) 0.0121(9) 0.0186(9) -0.0032(7) -0.0020(7) -0.0023(7) C8 0.0154(8) 0.0123(9) 0.0153(9) -0.0030(7) -0.0020(6) -0.0036(7) C6 0.0159(8) 0.0163(10) 0.0174(9) -0.0017(8) -0.0025(7) -0.0022(7) C12 0.0141(8) 0.0180(10) 0.0197(9) -0.0039(8) -0.0013(7) -0.0032(7) C9 0.0162(9) 0.0197(11) 0.0176(10) -0.0029(8) -0.0033(7) -0.0050(8) C11 0.0120(8) 0.0168(9) 0.0151(9) -0.0053(7) -0.0016(6) -0.0027(7) C3 0.0158(8) 0.0182(10) 0.0150(9) -0.0041(8) 0.0000(7) -0.0062(7) C5 0.0111(8) 0.0234(11) 0.0186(9) -0.0054(8) -0.0023(7) 0.0008(7) C4 0.0096(8) 0.0283(11) 0.0184(9) -0.0075(8) -0.0002(7) -0.0055(7) C14 0.0111(8) 0.0220(10) 0.0234(10) -0.0084(8) -0.0029(7) -0.0002(7) C13 0.0187(9) 0.0170(10) 0.0202(10) -0.0044(8) -0.0028(7) -0.0005(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 O8 N5 1.2251(19) . ? O6 C16 1.3213(19) . ? O6 H12 0.88(2) . ? O5 C16 1.219(2) . ? O7 N5 1.2346(18) . ? N5 C19 1.480(2) . ? C16 C17 1.488(2) . ? C20 C19 1.388(2) . ? C20 C21 1.400(3) . ? C20 H17 0.95(2) . ? C19 C18 1.379(3) . ? C17 C22 1.395(2) . ? C17 C18 1.399(2) . ? C18 H14 0.929(19) . ? C22 C21 1.383(3) . ? C22 H15 0.91(2) . ? C21 H16 0.925(19) . ? C15 N4 1.350(2) . ? C15 C14 1.375(3) . ? C15 H13 0.969(17) . ? S1 O1 1.4321(13) . ? S1 O2 1.4324(13) . ? S1 N1 1.6423(15) . ? S1 C1 1.7648(17) . ? O3 C8 1.336(2) . ? O3 H18 0.89(2) . ? O4 C10 1.242(2) . ? N1 C7 1.442(2) . ? N1 C9 1.486(2) . ? N3 C10 1.372(2) . ? N3 C11 1.415(2) . ? N3 H8 0.86(2) . ? N4 C11 1.343(2) . ? C1 C6 1.393(2) . ? C1 C2 1.402(2) . ? C10 C7 1.471(2) . ? C2 C3 1.401(2) . ? C2 C8 1.470(2) . ? C7 C8 1.373(2) . ? C6 C5 1.393(2) . ? C6 H4 0.926(19) . ? C12 C13 1.392(2) . ? C12 C11 1.397(2) . ? C12 H9 0.968(19) . ? C9 H6 0.97(2) . ? C9 H5 1.01(2) . ? C9 H7 0.98(2) . ? C3 C4 1.394(2) . ? C3 H1 0.942(18) . ? C5 C4 1.380(3) . ? C5 H3 0.93(2) . ? C4 H2 0.953(18) . ? C14 C13 1.387(3) . ? C14 H11 0.95(2) . ? C13 H10 1.01(2) . ? 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 C16 O6 H12 108.6(14) . . ? O8 N5 O7 123.51(14) . . ? O8 N5 C19 118.54(14) . . ? O7 N5 C19 117.95(14) . . ? O5 C16 O6 123.04(16) . . ? O5 C16 C17 122.39(15) . . ? O6 C16 C17 114.58(14) . . ? C19 C20 C21 117.89(17) . . ? C19 C20 H17 120.6(11) . . ? C21 C20 H17 121.5(11) . . ? C18 C19 C20 123.12(16) . . ? C18 C19 N5 118.50(14) . . ? C20 C19 N5 118.38(16) . . ? C22 C17 C18 119.95(17) . . ? C22 C17 C16 119.08(15) . . ? C18 C17 C16 120.97(15) . . ? C19 C18 C17 118.16(15) . . ? C19 C18 H14 120.5(12) . . ? C17 C18 H14 121.3(12) . . ? C21 C22 C17 120.58(16) . . ? C21 C22 H15 121.3(12) . . ? C17 C22 H15 118.2(12) . . ? C22 C21 C20 120.29(16) . . ? C22 C21 H16 122.9(12) . . ? C20 C21 H16 116.8(12) . . ? N4 C15 C14 123.17(17) . . ? N4 C15 H13 114.4(10) . . ? C14 C15 H13 122.4(10) . . ? O1 S1 O2 119.01(8) . . ? O1 S1 N1 108.05(7) . . ? O2 S1 N1 108.42(7) . . ? O1 S1 C1 108.97(8) . . ? O2 S1 C1 109.53(8) . . ? N1 S1 C1 101.40(8) . . ? C8 O3 H18 106.9(15) . . ? C7 N1 C9 115.03(15) . . ? C7 N1 S1 114.24(11) . . ? C9 N1 S1 116.20(11) . . ? C10 N3 C11 127.23(15) . . ? C10 N3 H8 116.9(13) . . ? C11 N3 H8 115.7(13) . . ? C11 N4 C15 118.52(15) . . ? C6 C1 C2 121.64(16) . . ? C6 C1 S1 121.22(14) . . ? C2 C1 S1 117.13(12) . . ? O4 C10 N3 123.10(15) . . ? O4 C10 C7 120.42(15) . . ? N3 C10 C7 116.48(15) . . ? C3 C2 C1 118.15(15) . . ? C3 C2 C8 120.78(16) . . ? C1 C2 C8 121.05(15) . . ? C8 C7 N1 120.82(14) . . ? C8 C7 C10 120.43(15) . . ? N1 C7 C10 118.75(14) . . ? O3 C8 C7 123.48(15) . . ? O3 C8 C2 114.52(14) . . ? C7 C8 C2 122.00(15) . . ? C1 C6 C5 118.83(17) . . ? C1 C6 H4 120.6(11) . . ? C5 C6 H4 120.6(11) . . ? C13 C12 C11 117.66(17) . . ? C13 C12 H9 120.2(11) . . ? C11 C12 H9 122.1(11) . . ? N1 C9 H6 108.6(12) . . ? N1 C9 H5 112.4(11) . . ? H6 C9 H5 111.7(16) . . ? N1 C9 H7 105.7(12) . . ? H6 C9 H7 110.8(16) . . ? H5 C9 H7 107.4(16) . . ? N4 C11 C12 122.35(15) . . ? N4 C11 N3 113.40(15) . . ? C12 C11 N3 124.25(15) . . ? C4 C3 C2 120.37(17) . . ? C4 C3 H1 119.2(10) . . ? C2 C3 H1 120.4(10) . . ? C4 C5 C6 120.60(16) . . ? C4 C5 H3 120.9(13) . . ? C6 C5 H3 118.5(13) . . ? C5 C4 C3 120.39(17) . . ? C5 C4 H2 122.1(11) . . ? C3 C4 H2 117.5(11) . . ? C15 C14 C13 117.85(16) . . ? C15 C14 H11 119.3(13) . . ? C13 C14 H11 122.8(13) . . ? C14 C13 C12 120.44(18) . . ? C14 C13 H10 120.2(10) . . ? C12 C13 H10 119.3(10) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.67 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.490 _refine_diff_density_min -0.375 _refine_diff_density_rms 0.058 # Attachment 'PXN 4FBA.cif' data_shelxl_PXN_4FBA _database_code_depnum_ccdc_archive 'CCDC 890553' #TrackingRef 'PXN 4FBA.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H13 N3 O4 S, C7 H5 F O2' _chemical_formula_sum 'C22 H18 F N3 O6 S' _chemical_formula_weight 471.45 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting tetragonal _symmetry_space_group_name_H-M P42/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x+1/2, z+1/2' '-x+1/2, -y+1/2, z' 'y+1/2, -x, z+1/2' '-x, -y, -z' 'y, -x-1/2, -z-1/2' 'x-1/2, y-1/2, -z' '-y-1/2, x, -z-1/2' _cell_length_a 24.4459(3) _cell_length_b 24.4459(3) _cell_length_c 6.97010(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4165.35(9) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 87528 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.485 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.504 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1952 _exptl_absorpt_coefficient_mu 0.212 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8870 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'SADABS (Blessing, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 37056 _diffrn_reflns_av_R_equivalents 0.1405 _diffrn_reflns_av_sigmaI/netI 0.0814 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.67 _diffrn_reflns_theta_max 27.49 _reflns_number_total 4762 _reflns_number_gt 2886 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo&Scalepack (Otwinowski,Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXS-97 (Sheldrick, 2008)' _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^)+(0.0527P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4762 _refine_ls_number_parameters 370 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0998 _refine_ls_R_factor_gt 0.0440 _refine_ls_wR_factor_ref 0.1058 _refine_ls_wR_factor_gt 0.0901 _refine_ls_goodness_of_fit_ref 0.956 _refine_ls_restrained_S_all 0.956 _refine_ls_shift/su_max 0.019 _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 H12 H 0.7782(7) 0.7143(8) -0.014(3) 0.024(5) Uiso 1 1 d . . . H17 H 0.8964(8) 0.6109(8) 0.187(3) 0.032(6) Uiso 1 1 d . . . H18 H 0.8687(8) 0.6983(8) 0.095(3) 0.028(6) Uiso 1 1 d . . . H8 H 0.3741(8) 0.5581(8) -0.376(3) 0.033(6) Uiso 1 1 d . . . H16 H 0.8349(7) 0.5376(8) 0.166(3) 0.022(5) Uiso 1 1 d . . . H14 H 0.6709(9) 0.5359(8) -0.406(4) 0.045(7) Uiso 1 1 d . . . H15 H 0.7091(7) 0.4907(9) -0.306(3) 0.028(6) Uiso 1 1 d . . . H1 H 0.5362(9) 0.3168(8) -0.152(3) 0.040(6) Uiso 1 1 d . . . H3 H 0.7221(9) 0.3033(8) 0.006(4) 0.040(6) Uiso 1 1 d . . . H4 H 0.6835(9) 0.3875(9) -0.066(3) 0.041(7) Uiso 1 1 d . . . H9 H 0.4137(8) 0.6454(8) -0.383(3) 0.032(6) Uiso 1 1 d . . . H7 H 0.4252(8) 0.4793(9) -0.303(3) 0.035(6) Uiso 1 1 d . . . H2 H 0.5777(9) 0.2311(10) -0.097(4) 0.053(7) Uiso 1 1 d . . . H6 H 0.5876(8) 0.5340(9) -0.177(4) 0.045(7) Uiso 1 1 d . . . H10 H 0.5078(8) 0.6539(9) -0.294(3) 0.038(6) Uiso 1 1 d . . . H13 H 0.7341(9) 0.5478(9) -0.353(3) 0.037(6) Uiso 1 1 d . . . H11 H 0.6365(10) 0.6938(9) -0.078(4) 0.067(8) Uiso 1 1 d . . . H5 H 0.5192(11) 0.4546(12) -0.205(4) 0.082(10) Uiso 1 1 d . . . S1 S 0.721989(19) 0.529155(19) 0.06150(8) 0.02295(15) Uani 1 1 d . . . O6 O 0.67922(5) 0.69590(5) -0.0415(2) 0.0260(3) Uani 1 1 d . . . O3 O 0.74895(5) 0.47904(5) 0.0144(2) 0.0279(4) Uani 1 1 d . . . O4 O 0.68947(5) 0.53198(5) 0.2317(2) 0.0263(4) Uani 1 1 d . . . O5 O 0.58781(5) 0.66106(5) -0.1501(2) 0.0267(4) Uani 1 1 d . . . F1 F 0.67527(5) 0.21075(5) -0.0154(2) 0.0530(4) Uani 1 1 d . . . N3 N 0.49424(6) 0.52084(6) -0.2513(3) 0.0280(4) Uani 1 1 d . . . O1 O 0.52965(6) 0.41752(6) -0.1804(2) 0.0316(4) Uani 1 1 d . . . C22 C 0.84319(8) 0.66889(8) 0.0837(3) 0.0256(5) Uani 1 1 d . . . N2 N 0.68362(6) 0.54736(6) -0.1194(3) 0.0219(4) Uani 1 1 d . . . C18 C 0.75289(7) 0.63495(7) 0.0129(3) 0.0215(5) Uani 1 1 d . . . C20 C 0.82369(8) 0.57326(8) 0.1309(3) 0.0252(5) Uani 1 1 d . . . O2 O 0.61174(6) 0.45699(6) -0.1644(2) 0.0381(4) Uani 1 1 d . . . C15 C 0.60553(8) 0.61295(8) -0.1527(3) 0.0237(5) Uani 1 1 d . . . C19 C 0.77072(8) 0.58242(8) 0.0684(3) 0.0237(5) Uani 1 1 d . . . C17 C 0.69623(8) 0.64369(7) -0.0497(3) 0.0221(5) Uani 1 1 d . . . C21 C 0.86007(8) 0.61686(8) 0.1376(3) 0.0266(5) Uani 1 1 d . . . C16 C 0.66280(8) 0.60225(7) -0.1061(3) 0.0223(5) Uani 1 1 d . . . C11 C 0.48934(8) 0.61792(9) -0.2973(3) 0.0273(5) Uani 1 1 d . . . C1 C 0.66162(9) 0.35671(9) -0.0695(4) 0.0382(6) Uani 1 1 d . . . C10 C 0.51782(8) 0.57039(8) -0.2485(3) 0.0239(5) Uani 1 1 d . . . C12 C 0.41026(9) 0.56266(9) -0.3488(4) 0.0334(6) Uani 1 1 d . . . N1 N 0.57328(6) 0.56909(7) -0.1952(3) 0.0247(4) Uani 1 1 d . . . C7 C 0.58362(8) 0.41614(8) -0.1555(3) 0.0273(5) Uani 1 1 d . . . C13 C 0.43487(9) 0.61324(9) -0.3478(3) 0.0302(5) Uani 1 1 d . . . C23 C 0.79027(8) 0.67779(8) 0.0217(3) 0.0248(5) Uani 1 1 d . . . C2 C 0.68497(10) 0.30640(9) -0.0342(4) 0.0444(7) Uani 1 1 d . . . C8 C 0.44102(9) 0.51794(9) -0.2998(4) 0.0346(6) Uani 1 1 d . . . C3 C 0.65246(9) 0.26096(9) -0.0468(4) 0.0368(6) Uani 1 1 d . . . C9 C 0.70179(9) 0.52996(9) -0.3136(3) 0.0262(5) Uani 1 1 d . . . C4 C 0.60673(8) 0.36122(8) -0.1154(3) 0.0283(5) Uani 1 1 d . . . C6 C 0.59786(10) 0.26346(9) -0.0888(4) 0.0440(7) Uani 1 1 d . . . C5 C 0.57471(10) 0.31429(9) -0.1212(4) 0.0397(6) 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 0.0225(3) 0.0195(3) 0.0268(3) 0.0004(2) -0.0013(2) -0.0008(2) O6 0.0239(7) 0.0182(7) 0.0360(9) -0.0008(6) -0.0033(7) 0.0010(6) O3 0.0264(8) 0.0207(7) 0.0368(10) -0.0006(7) -0.0036(7) 0.0031(6) O4 0.0267(8) 0.0238(7) 0.0282(9) 0.0014(6) 0.0018(7) -0.0028(6) O5 0.0237(7) 0.0206(7) 0.0357(10) -0.0001(7) -0.0030(7) 0.0020(6) F1 0.0494(8) 0.0339(7) 0.0757(12) 0.0097(7) 0.0012(8) 0.0115(6) N3 0.0233(9) 0.0281(9) 0.0326(12) -0.0014(8) -0.0019(8) -0.0025(7) O1 0.0286(8) 0.0249(8) 0.0411(11) 0.0017(7) -0.0029(7) -0.0036(7) C22 0.0233(11) 0.0262(11) 0.0274(14) -0.0038(10) 0.0011(9) -0.0051(9) N2 0.0218(9) 0.0185(8) 0.0253(11) -0.0012(7) -0.0029(7) 0.0012(7) C18 0.0218(10) 0.0198(10) 0.0230(13) -0.0017(9) 0.0011(9) -0.0006(8) C20 0.0260(11) 0.0219(11) 0.0276(13) 0.0002(10) 0.0002(10) 0.0019(9) O2 0.0313(8) 0.0243(8) 0.0585(12) 0.0009(8) -0.0034(8) -0.0064(7) C15 0.0238(11) 0.0245(11) 0.0226(13) 0.0012(9) 0.0005(9) -0.0018(9) C19 0.0236(11) 0.0249(11) 0.0227(12) -0.0015(9) 0.0015(9) -0.0014(8) C17 0.0261(11) 0.0180(10) 0.0223(12) 0.0002(9) 0.0015(9) 0.0017(8) C21 0.0205(11) 0.0325(12) 0.0268(13) -0.0014(10) -0.0020(10) 0.0003(9) C16 0.0216(10) 0.0195(10) 0.0258(13) 0.0002(9) -0.0003(9) 0.0002(8) C11 0.0259(12) 0.0267(12) 0.0292(14) 0.0013(10) 0.0014(10) -0.0032(9) C1 0.0300(13) 0.0288(13) 0.0560(18) -0.0006(12) 0.0023(12) -0.0020(10) C10 0.0214(11) 0.0277(11) 0.0226(12) 0.0006(9) 0.0016(9) -0.0038(9) C12 0.0199(12) 0.0403(14) 0.0399(16) 0.0000(11) -0.0042(11) -0.0054(10) N1 0.0210(9) 0.0211(9) 0.0319(12) 0.0005(8) -0.0027(8) -0.0017(7) C7 0.0296(12) 0.0285(12) 0.0240(14) -0.0037(10) -0.0013(10) -0.0037(10) C13 0.0250(12) 0.0358(13) 0.0297(14) 0.0017(11) 0.0001(10) 0.0019(10) C23 0.0254(11) 0.0217(11) 0.0273(14) 0.0000(10) 0.0025(10) -0.0013(9) C2 0.0285(13) 0.0423(15) 0.062(2) 0.0018(13) -0.0005(13) 0.0020(11) C8 0.0282(12) 0.0322(13) 0.0433(17) -0.0021(11) -0.0052(11) -0.0068(10) C3 0.0424(14) 0.0277(12) 0.0402(16) 0.0048(11) 0.0023(12) 0.0082(10) C9 0.0283(12) 0.0231(12) 0.0272(14) -0.0020(10) 0.0023(11) -0.0003(10) C4 0.0322(12) 0.0280(12) 0.0247(13) -0.0017(10) 0.0029(10) -0.0025(9) C6 0.0479(15) 0.0249(13) 0.059(2) 0.0045(12) -0.0127(13) -0.0053(11) C5 0.0365(14) 0.0287(13) 0.0538(18) 0.0011(11) -0.0153(12) -0.0041(10) _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 O3 1.4294(13) . ? S1 O4 1.4297(15) . ? S1 N2 1.6332(17) . ? S1 C19 1.7655(19) . ? O6 C17 1.343(2) . ? O6 H11 1.07(3) . ? O5 C15 1.254(2) . ? F1 C3 1.366(2) . ? N3 C10 1.342(2) . ? N3 C8 1.346(3) . ? O1 C7 1.331(2) . ? O1 H5 0.96(3) . ? C22 C23 1.381(3) . ? C22 C21 1.389(3) . ? C22 H18 0.96(2) . ? N2 C16 1.438(2) . ? N2 C9 1.487(3) . ? C18 C23 1.391(3) . ? C18 C19 1.410(3) . ? C18 C17 1.468(3) . ? C20 C19 1.384(3) . ? C20 C21 1.389(3) . ? C20 H16 0.947(18) . ? O2 C7 1.214(2) . ? C15 N1 1.364(2) . ? C15 C16 1.461(3) . ? C17 C16 1.360(3) . ? C21 H17 0.96(2) . ? C11 C13 1.382(3) . ? C11 C10 1.396(3) . ? C11 H10 0.99(2) . ? C1 C2 1.378(3) . ? C1 C4 1.384(3) . ? C1 H4 0.92(2) . ? C10 N1 1.406(2) . ? C12 C8 1.370(3) . ? C12 C13 1.375(3) . ? C12 H8 0.91(2) . ? N1 H6 0.94(2) . ? C7 C4 1.483(3) . ? C13 H9 0.97(2) . ? C23 H12 0.971(18) . ? C2 C3 1.369(3) . ? C2 H3 0.95(2) . ? C8 H7 1.02(2) . ? C3 C6 1.368(3) . ? C9 H14 1.00(2) . ? C9 H15 0.98(2) . ? C9 H13 0.94(2) . ? C4 C5 1.390(3) . ? C6 C5 1.384(3) . ? C6 H2 0.93(2) . ? C5 H1 0.97(2) . ? 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 O3 S1 O4 119.23(8) . . ? O3 S1 N2 108.73(9) . . ? O4 S1 N2 107.94(8) . . ? O3 S1 C19 109.10(8) . . ? O4 S1 C19 108.48(9) . . ? N2 S1 C19 101.99(9) . . ? C17 O6 H11 104.2(13) . . ? C10 N3 C8 117.80(18) . . ? C7 O1 H5 108.2(16) . . ? C23 C22 C21 120.49(19) . . ? C23 C22 H18 121.2(11) . . ? C21 C22 H18 118.3(11) . . ? C16 N2 C9 115.55(17) . . ? C16 N2 S1 114.07(13) . . ? C9 N2 S1 116.94(13) . . ? C23 C18 C19 118.06(17) . . ? C23 C18 C17 121.55(17) . . ? C19 C18 C17 120.39(16) . . ? C19 C20 C21 119.04(19) . . ? C19 C20 H16 120.1(11) . . ? C21 C20 H16 120.8(11) . . ? O5 C15 N1 122.76(18) . . ? O5 C15 C16 119.75(17) . . ? N1 C15 C16 117.49(17) . . ? C20 C19 C18 121.52(18) . . ? C20 C19 S1 121.36(15) . . ? C18 C19 S1 117.10(14) . . ? O6 C17 C16 122.28(17) . . ? O6 C17 C18 114.70(16) . . ? C16 C17 C18 122.99(17) . . ? C20 C21 C22 120.22(19) . . ? C20 C21 H17 119.0(12) . . ? C22 C21 H17 120.6(12) . . ? C17 C16 N2 120.08(17) . . ? C17 C16 C15 120.45(17) . . ? N2 C16 C15 119.47(16) . . ? C13 C11 C10 118.26(19) . . ? C13 C11 H10 121.2(12) . . ? C10 C11 H10 120.5(12) . . ? C2 C1 C4 120.9(2) . . ? C2 C1 H4 118.9(13) . . ? C4 C1 H4 120.1(13) . . ? N3 C10 C11 122.24(18) . . ? N3 C10 N1 113.42(17) . . ? C11 C10 N1 124.33(18) . . ? C8 C12 C13 118.4(2) . . ? C8 C12 H8 119.1(13) . . ? C13 C12 H8 122.4(13) . . ? C15 N1 C10 126.66(17) . . ? C15 N1 H6 118.3(13) . . ? C10 N1 H6 114.7(13) . . ? O2 C7 O1 122.25(19) . . ? O2 C7 C4 122.59(19) . . ? O1 C7 C4 115.16(17) . . ? C12 C13 C11 119.8(2) . . ? C12 C13 H9 119.6(12) . . ? C11 C13 H9 120.6(12) . . ? C22 C23 C18 120.68(19) . . ? C22 C23 H12 120.5(11) . . ? C18 C23 H12 118.8(11) . . ? C3 C2 C1 118.2(2) . . ? C3 C2 H3 120.5(13) . . ? C1 C2 H3 121.2(12) . . ? N3 C8 C12 123.4(2) . . ? N3 C8 H7 114.9(11) . . ? C12 C8 H7 121.6(11) . . ? F1 C3 C6 118.22(19) . . ? F1 C3 C2 118.8(2) . . ? C6 C3 C2 123.0(2) . . ? N2 C9 H14 108.5(13) . . ? N2 C9 H15 106.7(13) . . ? H14 C9 H15 108.3(16) . . ? N2 C9 H13 112.4(14) . . ? H14 C9 H13 112.2(19) . . ? H15 C9 H13 108.5(17) . . ? C1 C4 C5 119.2(2) . . ? C1 C4 C7 119.02(18) . . ? C5 C4 C7 121.81(19) . . ? C3 C6 C5 118.3(2) . . ? C3 C6 H2 119.4(14) . . ? C5 C6 H2 122.3(14) . . ? C6 C5 C4 120.4(2) . . ? C6 C5 H1 119.5(12) . . ? C4 C5 H1 120.1(12) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.250 _refine_diff_density_min -0.367 _refine_diff_density_rms 0.055 # Attachment 'PXZ 2ABA.cif' data_shelxl_PXZ_2ABA _database_code_depnum_ccdc_archive 'CCDC 890554' #TrackingRef 'PXZ 2ABA.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H13 N3 O4 S, C7 H7 N O2' _chemical_formula_sum 'C22 H20 N4 O6 S' _chemical_formula_weight 468.48 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.8637(6) _cell_length_b 11.6363(11) _cell_length_c 13.8047(12) _cell_angle_alpha 83.313(4) _cell_angle_beta 79.158(5) _cell_angle_gamma 73.738(5) _cell_volume 1037.17(16) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 168565 _cell_measurement_theta_min 1 _cell_measurement_theta_max 26.02 _exptl_crystal_description Plate _exptl_crystal_colour yellow _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.500 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 488 _exptl_absorpt_coefficient_mu 0.207 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.725 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'SADABS (Blessing, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 KappaCCD _diffrn_measurement_method 'CCD; rotation images' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17744 _diffrn_reflns_av_R_equivalents 0.0825 _diffrn_reflns_av_sigmaI/netI 0.0563 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 26.03 _reflns_number_total 4095 _reflns_number_gt 3035 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo&Scalepack (Otwinowski,Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0415P)^2^+0.7100P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4095 _refine_ls_number_parameters 378 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0770 _refine_ls_R_factor_gt 0.0476 _refine_ls_wR_factor_ref 0.1137 _refine_ls_wR_factor_gt 0.1003 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _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 H17 H 0.851(4) 0.462(2) 0.0415(18) 0.025(6) Uiso 1 1 d . . . H19 H 0.773(4) 0.673(2) 0.2673(17) 0.021(6) Uiso 1 1 d . . . H18 H 0.812(3) 0.654(2) 0.0970(17) 0.021(6) Uiso 1 1 d . . . H16 H 0.859(4) 0.295(2) 0.1566(18) 0.029(7) Uiso 1 1 d . . . H20 H 0.829(5) 0.215(3) 0.323(2) 0.050(9) Uiso 1 1 d . . . H22 H 0.739(6) 0.637(3) 0.499(3) 0.072(12) Uiso 1 1 d . . . H21 H 0.814(5) 0.292(3) 0.408(3) 0.053(10) Uiso 1 1 d . . . H13 H 0.205(4) 0.128(2) 0.1451(19) 0.028(7) Uiso 1 1 d . . . H14 H 0.255(4) 0.237(2) 0.0657(19) 0.029(7) Uiso 1 1 d . . . H3 H 0.374(4) -0.191(2) 0.4660(19) 0.034(7) Uiso 1 1 d . . . H5 H 0.294(4) 0.455(2) 0.294(2) 0.035(8) Uiso 1 1 d . . . H8 H 0.081(4) 0.868(2) 0.2895(19) 0.032(7) Uiso 1 1 d . . . H12 H 0.381(4) 0.098(2) 0.0486(19) 0.031(7) Uiso 1 1 d . . . H7 H 0.169(4) 0.659(2) 0.344(2) 0.041(8) Uiso 1 1 d . . . H9 H 0.150(4) 0.925(2) 0.1225(18) 0.027(7) Uiso 1 1 d . . . H2 H 0.167(4) -0.028(2) 0.558(2) 0.038(7) Uiso 1 1 d . . . H10 H 0.308(4) 0.776(2) 0.008(2) 0.032(7) Uiso 1 1 d . . . H4 H 0.566(4) -0.161(3) 0.312(2) 0.039(8) Uiso 1 1 d . . . H1 H 0.162(4) 0.173(2) 0.4915(19) 0.032(7) Uiso 1 1 d . . . H11 H 0.379(5) 0.582(3) 0.064(2) 0.065(10) Uiso 1 1 d . . . S1 S 0.62126(10) 0.05333(5) 0.19692(4) 0.02499(17) Uani 1 1 d . . . O4 O 0.4265(2) 0.40882(14) 0.07722(11) 0.0245(4) Uani 1 1 d . . . O1 O 0.2762(3) 0.33397(15) 0.37903(11) 0.0269(4) Uani 1 1 d . . . N2 N 0.3207(3) 0.48267(18) 0.23121(15) 0.0231(4) Uani 1 1 d . . . O3 O 0.6545(3) -0.04138(15) 0.13321(12) 0.0301(4) Uani 1 1 d . . . N1 N 0.4722(3) 0.17456(17) 0.15163(14) 0.0228(4) Uani 1 1 d . . . N3 N 0.3195(3) 0.64012(18) 0.10919(15) 0.0238(5) Uani 1 1 d . . . C6 C 0.3513(4) 0.1248(2) 0.36111(17) 0.0238(5) Uani 1 1 d . . . C8 C 0.4014(4) 0.2716(2) 0.21768(16) 0.0220(5) Uani 1 1 d . . . C7 C 0.3417(4) 0.2498(2) 0.31889(17) 0.0234(5) Uani 1 1 d . . . C10 C 0.2788(4) 0.6017(2) 0.20489(17) 0.0226(5) Uani 1 1 d . . . C11 C 0.1930(4) 0.6876(2) 0.27559(18) 0.0252(5) Uani 1 1 d . . . C15 C 0.3141(4) 0.1570(3) 0.0993(2) 0.0288(6) Uani 1 1 d . . . C14 C 0.2732(4) 0.7583(2) 0.07777(19) 0.0271(6) Uani 1 1 d . . . C5 C 0.4713(4) 0.0246(2) 0.30971(17) 0.0237(5) Uani 1 1 d . . . C4 C 0.4771(4) -0.0920(2) 0.34801(19) 0.0290(6) Uani 1 1 d . . . C13 C 0.1833(4) 0.8430(2) 0.1440(2) 0.0306(6) Uani 1 1 d . . . C3 C 0.3651(4) -0.1103(3) 0.4404(2) 0.0323(6) Uani 1 1 d . . . C1 C 0.2402(4) 0.1038(2) 0.45411(18) 0.0265(6) Uani 1 1 d . . . C12 C 0.1438(4) 0.8062(2) 0.24424(19) 0.0293(6) Uani 1 1 d . . . C2 C 0.2491(4) -0.0124(2) 0.49299(19) 0.0306(6) Uani 1 1 d . . . O5 O 0.7723(3) 0.43777(16) 0.48703(12) 0.0329(4) Uani 1 1 d . . . O6 O 0.7498(3) 0.63079(17) 0.43634(14) 0.0347(5) Uani 1 1 d . . . C20 C 0.7969(4) 0.4979(2) 0.31385(17) 0.0233(5) Uani 1 1 d . . . N4 N 0.8304(4) 0.2830(2) 0.34367(18) 0.0313(5) Uani 1 1 d . . . C16 C 0.8458(4) 0.3723(2) 0.17858(18) 0.0258(5) Uani 1 1 d . . . C21 C 0.8238(4) 0.3828(2) 0.28095(17) 0.0248(5) Uani 1 1 d . . . C19 C 0.7925(4) 0.5958(2) 0.24395(18) 0.0263(5) Uani 1 1 d . . . C18 C 0.8147(4) 0.5837(2) 0.14394(18) 0.0278(6) Uani 1 1 d . . . C22 C 0.7719(4) 0.5166(2) 0.42023(18) 0.0281(6) Uani 1 1 d . . . C17 C 0.8412(4) 0.4702(2) 0.11229(18) 0.0280(6) Uani 1 1 d . . . O2 O 0.7973(3) 0.08336(15) 0.21801(12) 0.0284(4) Uani 1 1 d . . . C9 C 0.3867(3) 0.3889(2) 0.16851(17) 0.0224(5) 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 0.0275(3) 0.0243(3) 0.0229(3) -0.0027(2) -0.0027(2) -0.0070(3) O4 0.0279(9) 0.0280(9) 0.0174(9) -0.0012(7) -0.0019(7) -0.0085(7) O1 0.0336(10) 0.0302(10) 0.0172(8) -0.0048(7) -0.0023(7) -0.0086(8) N2 0.0275(11) 0.0246(11) 0.0167(10) -0.0025(8) -0.0002(9) -0.0077(9) O3 0.0398(10) 0.0242(9) 0.0261(9) -0.0068(7) -0.0033(8) -0.0075(8) N1 0.0281(11) 0.0209(11) 0.0195(10) -0.0030(8) -0.0016(8) -0.0073(9) N3 0.0265(11) 0.0246(12) 0.0201(11) -0.0021(9) -0.0013(9) -0.0076(9) C6 0.0233(13) 0.0271(14) 0.0234(12) 0.0007(10) -0.0085(10) -0.0088(10) C8 0.0233(12) 0.0235(13) 0.0193(12) -0.0038(10) -0.0019(10) -0.0065(10) C7 0.0227(12) 0.0279(13) 0.0221(12) -0.0034(10) -0.0057(10) -0.0088(10) C10 0.0201(12) 0.0264(13) 0.0226(12) -0.0009(10) -0.0046(10) -0.0081(10) C11 0.0260(13) 0.0274(14) 0.0222(13) -0.0033(10) -0.0029(10) -0.0072(11) C15 0.0333(15) 0.0314(16) 0.0251(14) -0.0044(12) -0.0083(12) -0.0109(12) C14 0.0281(14) 0.0272(14) 0.0248(14) -0.0001(11) -0.0008(11) -0.0082(11) C5 0.0240(12) 0.0270(14) 0.0222(12) 0.0004(10) -0.0076(10) -0.0086(10) C4 0.0297(14) 0.0296(15) 0.0289(14) 0.0000(11) -0.0077(11) -0.0086(12) C13 0.0327(15) 0.0221(14) 0.0364(15) -0.0015(11) -0.0030(12) -0.0083(11) C3 0.0334(15) 0.0312(16) 0.0351(15) 0.0108(12) -0.0124(12) -0.0141(12) C1 0.0262(13) 0.0365(15) 0.0188(12) 0.0012(11) -0.0053(10) -0.0117(12) C12 0.0276(14) 0.0315(15) 0.0305(14) -0.0083(12) -0.0039(11) -0.0090(11) C2 0.0302(14) 0.0392(16) 0.0257(14) 0.0065(12) -0.0094(12) -0.0148(12) O5 0.0400(11) 0.0380(11) 0.0204(9) 0.0024(8) -0.0054(8) -0.0111(9) O6 0.0489(12) 0.0356(11) 0.0215(10) -0.0050(8) -0.0071(9) -0.0123(9) C20 0.0205(12) 0.0305(14) 0.0194(12) -0.0015(10) -0.0042(10) -0.0070(10) N4 0.0398(14) 0.0284(13) 0.0287(13) 0.0014(10) -0.0089(11) -0.0129(11) C16 0.0238(13) 0.0319(15) 0.0237(13) -0.0059(11) -0.0009(10) -0.0110(11) C21 0.0215(12) 0.0295(14) 0.0248(13) -0.0016(10) -0.0052(10) -0.0083(10) C19 0.0264(13) 0.0287(14) 0.0250(13) -0.0021(11) -0.0046(10) -0.0090(11) C18 0.0288(14) 0.0357(15) 0.0214(13) 0.0029(11) -0.0067(11) -0.0127(12) C22 0.0261(13) 0.0356(15) 0.0233(13) -0.0028(11) -0.0037(10) -0.0091(11) C17 0.0258(13) 0.0432(16) 0.0182(13) -0.0037(11) -0.0038(10) -0.0133(12) O2 0.0257(9) 0.0287(10) 0.0304(10) -0.0039(7) -0.0022(7) -0.0072(7) C9 0.0187(12) 0.0306(14) 0.0191(12) -0.0023(10) -0.0028(10) -0.0087(10) _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 O3 1.4317(17) . ? S1 O2 1.4350(17) . ? S1 N1 1.629(2) . ? S1 C5 1.751(2) . ? O4 C9 1.247(3) . ? O1 C7 1.286(3) . ? N2 C10 1.353(3) . ? N2 C9 1.393(3) . ? N2 H5 0.90(3) . ? N1 C8 1.452(3) . ? N1 C15 1.482(3) . ? N3 C10 1.348(3) . ? N3 C14 1.360(3) . ? N3 H11 0.94(3) . ? C6 C1 1.397(3) . ? C6 C5 1.406(3) . ? C6 C7 1.491(3) . ? C8 C7 1.395(3) . ? C8 C9 1.437(3) . ? C10 C11 1.408(3) . ? C11 C12 1.364(4) . ? C11 H7 0.97(3) . ? C15 H13 0.99(3) . ? C15 H14 1.00(3) . ? C15 H12 1.00(3) . ? C14 C13 1.358(4) . ? C14 H10 0.96(3) . ? C5 C4 1.390(3) . ? C4 C3 1.386(4) . ? C4 H4 0.99(3) . ? C13 C12 1.400(4) . ? C13 H9 0.94(3) . ? C3 C2 1.388(4) . ? C3 H3 0.96(3) . ? C1 C2 1.385(4) . ? C1 H1 0.98(3) . ? C12 H8 0.96(3) . ? C2 H2 0.99(3) . ? O5 C22 1.222(3) . ? O6 C22 1.335(3) . ? O6 H22 0.86(4) . ? C20 C19 1.402(3) . ? C20 C21 1.416(3) . ? C20 C22 1.481(3) . ? N4 C21 1.361(3) . ? N4 H20 0.87(3) . ? N4 H21 0.88(3) . ? C16 C17 1.373(4) . ? C16 C21 1.409(3) . ? C16 H16 0.96(3) . ? C19 C18 1.380(3) . ? C19 H19 0.95(2) . ? C18 C17 1.392(4) . ? C18 H18 0.98(2) . ? C17 H17 0.98(2) . ? 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 O3 S1 O2 118.39(11) . . ? O3 S1 N1 108.86(10) . . ? O2 S1 N1 108.03(10) . . ? O3 S1 C5 110.25(11) . . ? O2 S1 C5 107.89(10) . . ? N1 S1 C5 102.18(11) . . ? C10 N2 C9 127.2(2) . . ? C10 N2 H5 121.8(17) . . ? C9 N2 H5 110.6(17) . . ? C8 N1 C15 115.17(19) . . ? C8 N1 S1 113.78(15) . . ? C15 N1 S1 116.21(16) . . ? C10 N3 C14 122.7(2) . . ? C10 N3 H11 117(2) . . ? C14 N3 H11 120(2) . . ? C1 C6 C5 117.8(2) . . ? C1 C6 C7 120.5(2) . . ? C5 C6 C7 121.7(2) . . ? C7 C8 C9 124.5(2) . . ? C7 C8 N1 121.2(2) . . ? C9 C8 N1 114.15(19) . . ? O1 C7 C8 122.6(2) . . ? O1 C7 C6 117.4(2) . . ? C8 C7 C6 120.0(2) . . ? N3 C10 N2 120.0(2) . . ? N3 C10 C11 118.6(2) . . ? N2 C10 C11 121.4(2) . . ? C12 C11 C10 118.9(2) . . ? C12 C11 H7 123.0(16) . . ? C10 C11 H7 118.1(17) . . ? N1 C15 H13 112.1(14) . . ? N1 C15 H14 106.0(14) . . ? H13 C15 H14 111(2) . . ? N1 C15 H12 109.1(14) . . ? H13 C15 H12 109(2) . . ? H14 C15 H12 110(2) . . ? C13 C14 N3 120.0(2) . . ? C13 C14 H10 124.1(16) . . ? N3 C14 H10 116.0(16) . . ? C4 C5 C6 121.8(2) . . ? C4 C5 S1 121.36(19) . . ? C6 C5 S1 116.76(18) . . ? C3 C4 C5 119.2(2) . . ? C3 C4 H4 120.2(16) . . ? C5 C4 H4 120.5(16) . . ? C14 C13 C12 118.8(2) . . ? C14 C13 H9 120.4(15) . . ? C12 C13 H9 120.9(15) . . ? C4 C3 C2 119.7(2) . . ? C4 C3 H3 117.9(16) . . ? C2 C3 H3 122.4(16) . . ? C2 C1 C6 120.3(2) . . ? C2 C1 H1 121.6(15) . . ? C6 C1 H1 118.0(15) . . ? C11 C12 C13 121.1(2) . . ? C11 C12 H8 121.8(16) . . ? C13 C12 H8 117.2(16) . . ? C1 C2 C3 121.1(2) . . ? C1 C2 H2 121.1(16) . . ? C3 C2 H2 117.7(16) . . ? C22 O6 H22 109(2) . . ? C19 C20 C21 119.0(2) . . ? C19 C20 C22 119.7(2) . . ? C21 C20 C22 121.3(2) . . ? C21 N4 H20 121(2) . . ? C21 N4 H21 117(2) . . ? H20 N4 H21 120(3) . . ? C17 C16 C21 121.3(2) . . ? C17 C16 H16 120.8(15) . . ? C21 C16 H16 117.8(15) . . ? N4 C21 C16 119.1(2) . . ? N4 C21 C20 122.9(2) . . ? C16 C21 C20 118.0(2) . . ? C18 C19 C20 122.2(2) . . ? C18 C19 H19 119.8(14) . . ? C20 C19 H19 118.0(14) . . ? C19 C18 C17 118.4(2) . . ? C19 C18 H18 119.9(14) . . ? C17 C18 H18 121.7(14) . . ? O5 C22 O6 122.7(2) . . ? O5 C22 C20 124.9(2) . . ? O6 C22 C20 112.4(2) . . ? C16 C17 C18 121.1(2) . . ? C16 C17 H17 120.5(14) . . ? C18 C17 H17 118.4(14) . . ? O4 C9 N2 120.9(2) . . ? O4 C9 C8 124.4(2) . . ? N2 C9 C8 114.7(2) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.03 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.216 _refine_diff_density_min -0.435 _refine_diff_density_rms 0.057 # Attachment 'PXZ 2BRBA.cif' data_shelxl_PXZ_2BRBA _database_code_depnum_ccdc_archive 'CCDC 890555' #TrackingRef 'PXZ 2BRBA.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H13 N3 O4 S, C7 H5 Br O2' _chemical_formula_sum 'C22 H18 Br N3 O6 S' _chemical_formula_weight 532.37 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1250 0.1230 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2900 2.4600 '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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.8280(5) _cell_length_b 10.9297(6) _cell_length_c 12.2953(11) _cell_angle_alpha 105.494(4) _cell_angle_beta 98.381(4) _cell_angle_gamma 105.396(3) _cell_volume 1071.81(13) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 26796 _cell_measurement_theta_min 1 _cell_measurement_theta_max 56.82 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.650 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 540 _exptl_absorpt_coefficient_mu 2.062 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7141 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'SADABS (Blessing, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'Bruker Apex II CCD' _diffrn_measurement_method 'CCD; rotation images' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26796 _diffrn_reflns_av_R_equivalents 0.1107 _diffrn_reflns_av_sigmaI/netI 0.0571 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 28.29 _reflns_number_total 5269 _reflns_number_gt 4373 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2 (2009)' _computing_cell_refinement 'Bruker APEX2 (2009)' _computing_data_reduction 'Bruker APEX2 (2009)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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. Hydrogen refinement details: Hydrogen atoms not involved in hydrogen bonds were placed on calculated positions and refined as riding on the atoms to which they were bonded. The H-atoms involved in hydrogen bonds were then identified using the Fourier difference synthesis. ; _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^)+(0.0561P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5269 _refine_ls_number_parameters 322 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0481 _refine_ls_R_factor_gt 0.0369 _refine_ls_wR_factor_ref 0.0969 _refine_ls_wR_factor_gt 0.0926 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _refine_ls_shift/su_max 0.003 _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 H5 H 0.138(4) 0.564(3) 0.656(2) 0.026(8) Uiso 1 1 d . . . H13 H 0.430(3) 0.405(3) 0.911(2) 0.021(7) Uiso 1 1 d . . . H12 H 0.535(4) 0.461(3) 0.827(2) 0.031(8) Uiso 1 1 d . . . H11 H 0.535(3) 0.324(3) 0.849(2) 0.029(8) Uiso 1 1 d . . . H10 H 0.396(4) 0.589(4) 0.496(3) 0.039(9) Uiso 1 1 d . . . H18 H 0.115(5) 0.449(4) 0.219(3) 0.067(12) Uiso 1 1 d . . . Br1 Br 0.24364(3) 0.13925(2) 0.391555(18) 0.01876(8) Uani 1 1 d . . . O6 O 0.0325(2) 0.24285(17) 0.23641(15) 0.0217(4) Uani 1 1 d . . . O5 O 0.1942(2) 0.41479(17) 0.19802(15) 0.0210(4) Uani 1 1 d . . . C16 C 0.3351(3) 0.1600(2) 0.26490(18) 0.0162(4) Uani 1 1 d . . . C22 C 0.1575(3) 0.2952(2) 0.21329(18) 0.0156(4) Uani 1 1 d . . . C19 C 0.4788(3) 0.1834(2) 0.0809(2) 0.0209(5) Uani 1 1 d . . . H16 H 0.5243 0.1891 0.0181 0.025 Uiso 1 1 calc R . . C20 C 0.5283(3) 0.1154(2) 0.1525(2) 0.0215(5) Uani 1 1 d . . . H15 H 0.6094 0.0776 0.1389 0.026 Uiso 1 1 calc R . . C21 C 0.4569(3) 0.1036(2) 0.2445(2) 0.0188(5) Uani 1 1 d . . . H14 H 0.4904 0.0582 0.2924 0.023 Uiso 1 1 calc R . . C18 C 0.3610(3) 0.2430(2) 0.10344(19) 0.0177(4) Uani 1 1 d . . . H17 H 0.3305 0.2908 0.0567 0.021 Uiso 1 1 calc R . . C17 C 0.2875(3) 0.2322(2) 0.19542(19) 0.0156(4) Uani 1 1 d . . . S1 S 0.22374(6) 0.16454(5) 0.72072(4) 0.01382(12) Uani 1 1 d . . . N1 N 0.3349(2) 0.31724(18) 0.73716(16) 0.0141(4) Uani 1 1 d . . . O4 O 0.41690(19) 0.47359(16) 0.59720(13) 0.0182(3) Uani 1 1 d . . . O1 O 0.13138(19) 0.10504(16) 0.60308(13) 0.0181(3) Uani 1 1 d . . . O2 O 0.3266(2) 0.09849(16) 0.76593(14) 0.0203(3) Uani 1 1 d . . . N2 N 0.2150(2) 0.5661(2) 0.62331(17) 0.0181(4) Uani 1 1 d . . . C1 C 0.0292(3) 0.1006(2) 0.86598(18) 0.0175(4) Uani 1 1 d . . . H1 H 0.0568 0.0224 0.8545 0.021 Uiso 1 1 calc R . . C10 C 0.2390(3) 0.6455(2) 0.55408(18) 0.0156(4) Uani 1 1 d . . . O3 O 0.0301(2) 0.48824(17) 0.75210(16) 0.0245(4) Uani 1 1 d . . . C9 C 0.3011(3) 0.4805(2) 0.64149(19) 0.0157(4) Uani 1 1 d . . . C2 C 0.0916(3) 0.1939(2) 0.81218(18) 0.0144(4) Uani 1 1 d . . . N3 N 0.3476(2) 0.6392(2) 0.48864(17) 0.0164(4) Uani 1 1 d . . . C13 C 0.2951(3) 0.8043(2) 0.4131(2) 0.0199(5) Uani 1 1 d . . . H8 H 0.3145 0.8571 0.3654 0.024 Uiso 1 1 calc R . . C12 C 0.1806(3) 0.8141(2) 0.48042(19) 0.0190(5) Uani 1 1 d . . . H6 H 0.1240 0.8743 0.4778 0.023 Uiso 1 1 calc R . . C11 C 0.1520(3) 0.7351(2) 0.55002(19) 0.0176(4) Uani 1 1 d . . . H7 H 0.0755 0.7409 0.5941 0.021 Uiso 1 1 calc R . . C14 C 0.3774(3) 0.7158(2) 0.41897(19) 0.0176(4) Uani 1 1 d . . . H9 H 0.4539 0.7081 0.3752 0.021 Uiso 1 1 calc R . . C6 C -0.0748(3) 0.1269(2) 0.9369(2) 0.0199(5) Uani 1 1 d . . . H2 H -0.1175 0.0660 0.9735 0.024 Uiso 1 1 calc R . . C15 C 0.4710(3) 0.3823(3) 0.8405(2) 0.0220(5) Uani 1 1 d . . . C7 C 0.1093(3) 0.4070(2) 0.76196(19) 0.0175(4) Uani 1 1 d . . . C3 C 0.0504(3) 0.3112(2) 0.82576(19) 0.0163(4) Uani 1 1 d . . . C4 C -0.0568(3) 0.3340(2) 0.8970(2) 0.0197(5) Uani 1 1 d . . . H4 H -0.0885 0.4101 0.9065 0.024 Uiso 1 1 calc R . . C5 C -0.1153(3) 0.2437(2) 0.9533(2) 0.0208(5) Uani 1 1 d . . . H3 H -0.1826 0.2617 1.0027 0.025 Uiso 1 1 calc R . . C8 C 0.2422(3) 0.4026(2) 0.71440(19) 0.0160(4) 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 Br1 0.01940(13) 0.02173(13) 0.01911(12) 0.01010(9) 0.00446(9) 0.00941(10) O6 0.0206(9) 0.0221(9) 0.0317(9) 0.0154(7) 0.0112(7) 0.0120(7) O5 0.0162(8) 0.0188(8) 0.0357(9) 0.0139(7) 0.0101(7) 0.0104(7) C16 0.0169(11) 0.0153(10) 0.0163(10) 0.0049(8) 0.0033(8) 0.0055(9) C22 0.0164(11) 0.0171(11) 0.0175(10) 0.0076(9) 0.0047(9) 0.0097(9) C19 0.0200(12) 0.0242(12) 0.0240(11) 0.0108(10) 0.0096(10) 0.0104(10) C20 0.0165(11) 0.0229(12) 0.0293(12) 0.0091(10) 0.0059(10) 0.0120(10) C21 0.0164(11) 0.0193(11) 0.0242(11) 0.0095(9) 0.0017(9) 0.0104(9) C18 0.0166(11) 0.0172(11) 0.0230(11) 0.0089(9) 0.0045(9) 0.0089(9) C17 0.0140(11) 0.0138(10) 0.0189(10) 0.0052(8) 0.0021(8) 0.0054(9) S1 0.0138(3) 0.0139(3) 0.0176(3) 0.0076(2) 0.0035(2) 0.0082(2) N1 0.0124(9) 0.0135(9) 0.0194(9) 0.0082(7) 0.0022(7) 0.0066(7) O4 0.0179(8) 0.0207(8) 0.0242(8) 0.0120(7) 0.0084(7) 0.0127(7) O1 0.0187(8) 0.0188(8) 0.0190(8) 0.0061(6) 0.0041(6) 0.0096(7) O2 0.0195(8) 0.0205(8) 0.0296(9) 0.0144(7) 0.0068(7) 0.0134(7) N2 0.0179(10) 0.0209(10) 0.0267(10) 0.0151(8) 0.0112(8) 0.0132(8) C1 0.0173(11) 0.0169(11) 0.0184(10) 0.0076(9) 0.0000(9) 0.0060(9) C10 0.0138(11) 0.0155(10) 0.0182(10) 0.0064(8) 0.0015(8) 0.0059(9) O3 0.0262(9) 0.0242(9) 0.0409(10) 0.0214(8) 0.0194(8) 0.0194(8) C9 0.0155(11) 0.0132(10) 0.0199(10) 0.0062(8) 0.0034(9) 0.0065(9) C2 0.0128(10) 0.0152(10) 0.0161(10) 0.0056(8) 0.0017(8) 0.0060(8) N3 0.0147(9) 0.0176(9) 0.0213(9) 0.0088(8) 0.0036(8) 0.0101(8) C13 0.0197(12) 0.0224(12) 0.0223(11) 0.0127(9) 0.0041(9) 0.0090(10) C12 0.0176(11) 0.0183(11) 0.0241(11) 0.0084(9) 0.0020(9) 0.0108(9) C11 0.0161(11) 0.0189(11) 0.0228(11) 0.0086(9) 0.0059(9) 0.0108(9) C14 0.0168(11) 0.0207(11) 0.0197(11) 0.0101(9) 0.0053(9) 0.0087(9) C6 0.0182(11) 0.0213(12) 0.0212(11) 0.0124(9) 0.0022(9) 0.0035(10) C15 0.0171(12) 0.0236(13) 0.0244(12) 0.0104(10) 0.0008(10) 0.0043(10) C7 0.0198(12) 0.0133(10) 0.0229(11) 0.0074(9) 0.0060(9) 0.0088(9) C3 0.0157(11) 0.0162(11) 0.0186(10) 0.0066(9) 0.0039(9) 0.0064(9) C4 0.0199(12) 0.0191(11) 0.0238(11) 0.0082(9) 0.0076(9) 0.0094(10) C5 0.0184(12) 0.0253(12) 0.0206(11) 0.0082(10) 0.0078(9) 0.0072(10) C8 0.0169(11) 0.0141(10) 0.0211(10) 0.0075(9) 0.0046(9) 0.0096(9) _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 Br1 C16 1.894(2) . ? O6 C22 1.212(3) . ? O5 C22 1.332(3) . ? O5 H18 0.91(4) . ? C16 C21 1.395(3) . ? C16 C17 1.401(3) . ? C22 C17 1.501(3) . ? C19 C18 1.389(3) . ? C19 C20 1.390(3) . ? C19 H16 0.9300 . ? C20 C21 1.391(3) . ? C20 H15 0.9300 . ? C21 H14 0.9300 . ? C18 C17 1.399(3) . ? C18 H17 0.9300 . ? S1 O1 1.4324(16) . ? S1 O2 1.4385(15) . ? S1 N1 1.6376(19) . ? S1 C2 1.765(2) . ? N1 C8 1.449(3) . ? N1 C15 1.477(3) . ? O4 C9 1.236(3) . ? N2 C10 1.369(3) . ? N2 C9 1.393(3) . ? N2 H5 0.84(3) . ? C1 C6 1.388(3) . ? C1 C2 1.396(3) . ? C1 H1 0.9300 . ? C10 N3 1.342(3) . ? C10 C11 1.402(3) . ? O3 C7 1.286(3) . ? C9 C8 1.452(3) . ? C2 C3 1.399(3) . ? N3 C14 1.355(3) . ? N3 H10 0.79(4) . ? C13 C14 1.365(3) . ? C13 C12 1.404(3) . ? C13 H8 0.9300 . ? C12 C11 1.372(3) . ? C12 H6 0.9300 . ? C11 H7 0.9300 . ? C14 H9 0.9300 . ? C6 C5 1.388(3) . ? C6 H2 0.9300 . ? C15 H13 0.99(3) . ? C15 H12 0.96(3) . ? C15 H11 0.97(3) . ? C7 C8 1.391(3) . ? C7 C3 1.500(3) . ? C3 C4 1.405(3) . ? C4 C5 1.385(3) . ? C4 H4 0.9300 . ? C5 H3 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C22 O5 H18 105(3) . . ? C21 C16 C17 120.4(2) . . ? C21 C16 Br1 117.48(16) . . ? C17 C16 Br1 122.14(16) . . ? O6 C22 O5 123.83(19) . . ? O6 C22 C17 124.4(2) . . ? O5 C22 C17 111.78(18) . . ? C18 C19 C20 119.8(2) . . ? C18 C19 H16 120.1 . . ? C20 C19 H16 120.1 . . ? C19 C20 C21 120.1(2) . . ? C19 C20 H15 120.0 . . ? C21 C20 H15 120.0 . . ? C20 C21 C16 120.1(2) . . ? C20 C21 H14 120.0 . . ? C16 C21 H14 120.0 . . ? C19 C18 C17 121.0(2) . . ? C19 C18 H17 119.5 . . ? C17 C18 H17 119.5 . . ? C18 C17 C16 118.68(19) . . ? C18 C17 C22 118.56(19) . . ? C16 C17 C22 122.74(19) . . ? O1 S1 O2 119.00(10) . . ? O1 S1 N1 108.30(9) . . ? O2 S1 N1 108.06(10) . . ? O1 S1 C2 108.67(10) . . ? O2 S1 C2 109.57(10) . . ? N1 S1 C2 101.86(10) . . ? C8 N1 C15 114.34(18) . . ? C8 N1 S1 113.75(14) . . ? C15 N1 S1 116.59(15) . . ? C10 N2 C9 126.75(19) . . ? C10 N2 H5 119(2) . . ? C9 N2 H5 115(2) . . ? C6 C1 C2 118.6(2) . . ? C6 C1 H1 120.7 . . ? C2 C1 H1 120.7 . . ? N3 C10 N2 120.26(19) . . ? N3 C10 C11 118.60(19) . . ? N2 C10 C11 121.14(19) . . ? O4 C9 N2 121.14(19) . . ? O4 C9 C8 124.44(19) . . ? N2 C9 C8 114.42(19) . . ? C1 C2 C3 122.2(2) . . ? C1 C2 S1 120.29(17) . . ? C3 C2 S1 117.51(16) . . ? C10 N3 C14 123.01(19) . . ? C10 N3 H10 114(2) . . ? C14 N3 H10 123(2) . . ? C14 C13 C12 118.8(2) . . ? C14 C13 H8 120.6 . . ? C12 C13 H8 120.6 . . ? C11 C12 C13 120.2(2) . . ? C11 C12 H6 119.9 . . ? C13 C12 H6 119.9 . . ? C12 C11 C10 119.4(2) . . ? C12 C11 H7 120.3 . . ? C10 C11 H7 120.3 . . ? N3 C14 C13 119.9(2) . . ? N3 C14 H9 120.0 . . ? C13 C14 H9 120.0 . . ? C5 C6 C1 120.3(2) . . ? C5 C6 H2 119.9 . . ? C1 C6 H2 119.9 . . ? N1 C15 H13 110.2(15) . . ? N1 C15 H12 104.7(17) . . ? H13 C15 H12 112(2) . . ? N1 C15 H11 111.3(17) . . ? H13 C15 H11 108(2) . . ? H12 C15 H11 110(2) . . ? O3 C7 C8 123.1(2) . . ? O3 C7 C3 117.22(19) . . ? C8 C7 C3 119.65(19) . . ? C2 C3 C4 117.7(2) . . ? C2 C3 C7 122.06(19) . . ? C4 C3 C7 120.1(2) . . ? C5 C4 C3 120.3(2) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? C4 C5 C6 120.9(2) . . ? C4 C5 H3 119.6 . . ? C6 C5 H3 119.6 . . ? C7 C8 N1 120.46(18) . . ? C7 C8 C9 124.88(19) . . ? N1 C8 C9 114.66(18) . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 28.29 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 1.197 _refine_diff_density_min -0.577 _refine_diff_density_rms 0.108 # Attachment 'PXZ 2CLBA.cif' data_shelxl_PXZ_2CLBA _database_code_depnum_ccdc_archive 'CCDC 890556' #TrackingRef 'PXZ 2CLBA.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H13 N3 O4 S, C7 H5 Cl O2' _chemical_formula_sum 'C22 H18 Cl N3 O6 S' _chemical_formula_weight 487.92 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0030 0.0020 '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' Cl Cl 0.1420 0.1500 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0100 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1190 0.1160 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c 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 19.768(17) _cell_length_b 6.917(6) _cell_length_c 31.56(3) _cell_angle_alpha 90.00 _cell_angle_beta 100.693(12) _cell_angle_gamma 90.00 _cell_volume 4240(7) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7257 _cell_measurement_theta_min 1.8 _cell_measurement_theta_max 26.7 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.529 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2016 _exptl_absorpt_coefficient_mu 0.251 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6121 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'ABSCOR, Rigaku 1995' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.68890 _diffrn_radiation_type synchrotron _diffrn_radiation_source synchrotron _diffrn_radiation_monochromator 'silicon 111' _diffrn_measurement_device_type 'Rigaku Saturn CCD' _diffrn_measurement_method 'profile data from \w-scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 36761 _diffrn_reflns_av_R_equivalents 0.1402 _diffrn_reflns_av_sigmaI/netI 0.1574 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -41 _diffrn_reflns_limit_l_max 39 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 26.68 _reflns_number_total 9709 _reflns_number_gt 5087 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010)' _computing_cell_refinement 'CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010)' _computing_data_reduction 'CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010' _computing_structure_solution 'SHELXS-86(Sheldrick, 1997)' _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. Hydrogen refinement details: Hydrogen atoms not involved in hydrogen bonds were placed on calculated positions and refined as riding on the atoms to which they were bonded. The H-atoms involved in hydrogen bonds were then identified using the Fourier difference synthesis. Problem: PLAT213_ALERT_2_B Atom O10 has ADP max/min Ratio .....4.6 prola PLAT230_ALERT_2_B Hirshfeld Test Diff for S2 -- O5 ..9.0 su PLAT250_ALERT_2_B Large U3/U1 Ratio for Average U(i,j) Tensor ....4.8 PLAT250_ALERT_2_B Large U3/U1 Ratio for Average U(i,j) Tensor ....5.9 PLAT250_ALERT_2_B Large U3/U1 Ratio for Average U(i,j) Tensor ....6.3 PLAT250_ALERT_2_B Large U3/U1 Ratio for Average U(i,j) Tensor ....5.5 RFACG01_ALERT_3_C The value of the R factor is > 0.10 R factor given 0.110 RFACR01_ALERT_3_C The value of the weighted R factor is > 0.25 Weighted R factor given 0.280 RINTA01_ALERT_3_C The value of Rint is greater than 0.12 Rint given 0.140 PLAT020_ALERT_3_C The value of Rint is greater than 0.12 .........0.140 PLAT213_ALERT_2_C Atom O1 has ADP max/min Ratio .....3.3 prola PLAT213_ALERT_2_C Atom O7 has ADP max/min Ratio .....3.3 prola PLAT213_ALERT_2_C Atom O9 has ADP max/min Ratio .....3.8 prola PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C34 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C31 PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds ...............0.0086 Ang Response: Very small, needle shaped crystals meant data collection could not be carried out using a lab source and so beamline I19 at the Diamond Synchotron facility was used. The data presented is the best available although still of low quality due to the extremely poor quality of the crystals. Many of the thermal parameters are elongated in the same direction. The space group symmetry was thus reduced but the model obtained was poorer. This may indicate strong pseudo-symmetry which results in the P21/c model representing the best possible solution. The resultant interpretation of the data was deemed sufficient for identifying the piroxicam tautomer present and for a tentative structure description. ; _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^)+(0.0989P)^2^+4.6477P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 9709 _refine_ls_number_parameters 613 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1874 _refine_ls_R_factor_gt 0.1103 _refine_ls_wR_factor_ref 0.2803 _refine_ls_wR_factor_gt 0.2314 _refine_ls_goodness_of_fit_ref 1.094 _refine_ls_restrained_S_all 1.094 _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 C15 C 0.0965(3) 0.4876(10) 0.36835(19) 0.0504(17) Uani 1 1 d . . . H26 H 0.1417 0.4405 0.3802 0.076 Uiso 1 1 calc R . . H25 H 0.0890 0.4797 0.3375 0.076 Uiso 1 1 calc R . . H24 H 0.0627 0.4105 0.3788 0.076 Uiso 1 1 calc R . . H16 H 0.118(3) 0.189(10) 0.160(2) 0.06(2) Uiso 1 1 d . . . H6 H -0.120(3) 0.690(10) 0.425(2) 0.07(2) Uiso 1 1 d . . . H31 H -0.160(4) 0.208(10) 0.452(3) 0.07(2) Uiso 1 1 d . . . H36 H 0.409(3) 0.170(8) 0.279(2) 0.045(18) Uiso 1 1 d . . . S1 S 0.14689(7) 0.8391(3) 0.36824(4) 0.0438(4) Uani 1 1 d . . . Cl1 Cl -0.03917(7) 0.1504(3) 0.33240(5) 0.0583(5) Uani 1 1 d . . . O2 O 0.12135(19) 1.0323(7) 0.37081(11) 0.0457(11) Uani 1 1 d . . . O4 O -0.04087(18) 0.6777(7) 0.39860(12) 0.0487(12) Uani 1 1 d . . . N3 N 0.0903(2) 0.6885(8) 0.38129(14) 0.0393(12) Uani 1 1 d . . . O3 O 0.12568(18) 0.7505(7) 0.49857(11) 0.0449(11) Uani 1 1 d . . . N1 N -0.0040(2) 0.7279(7) 0.47082(14) 0.0380(12) Uani 1 1 d . . . H5 H 0.0317 0.7405 0.4908 0.046 Uiso 1 1 calc R . . O1 O 0.1633(2) 0.7751(7) 0.32810(12) 0.0518(12) Uani 1 1 d . . . N2 N -0.1242(2) 0.6971(7) 0.45416(14) 0.0368(12) Uani 1 1 d . . . O10 O -0.0817(3) 0.1858(15) 0.41411(16) 0.152(4) Uani 1 1 d . . . C8 C 0.0072(3) 0.7053(9) 0.42912(18) 0.0379(14) Uani 1 1 d . . . C37 C -0.1274(3) 0.1772(9) 0.31971(17) 0.0345(13) Uani 1 1 d . . . C3 C 0.2852(3) 0.8272(11) 0.4019(2) 0.0554(19) Uani 1 1 d . . . H3 H 0.2928 0.8623 0.3747 0.066 Uiso 1 1 calc R . . O9 O -0.1849(2) 0.2088(10) 0.42241(14) 0.080(2) Uani 1 1 d . . . C5 C 0.2181(3) 0.8044(10) 0.40975(17) 0.0454(16) Uani 1 1 d . . . C31 C -0.1390(3) 0.2004(10) 0.39822(17) 0.0406(15) Uani 1 1 d . . . C32 C -0.1679(3) 0.1979(8) 0.35146(16) 0.0328(13) Uani 1 1 d . . . C7 C 0.0790(3) 0.7155(10) 0.42517(16) 0.0437(16) Uani 1 1 d . . . C36 C -0.1568(3) 0.1790(9) 0.27648(18) 0.0418(15) Uani 1 1 d . . . H27 H -0.1290 0.1685 0.2558 0.050 Uiso 1 1 calc R . . C6 C 0.1336(3) 0.7378(10) 0.45927(17) 0.0426(15) Uani 1 1 d . . . C9 C -0.0669(3) 0.7320(8) 0.48320(16) 0.0325(13) Uani 1 1 d . . . C2 C 0.3396(3) 0.7959(13) 0.43564(19) 0.064(2) Uani 1 1 d . . . H2 H 0.3845 0.8090 0.4311 0.077 Uiso 1 1 calc R . . C1 C 0.2613(3) 0.7263(11) 0.48388(18) 0.0509(18) Uani 1 1 d . . . H1 H 0.2542 0.6948 0.5114 0.061 Uiso 1 1 calc R . . C10 C -0.0716(3) 0.7754(9) 0.52593(17) 0.0391(14) Uani 1 1 d . . . H10 H -0.0325 0.7989 0.5467 0.047 Uiso 1 1 calc R . . C4 C 0.2050(3) 0.7541(10) 0.45062(17) 0.0444(16) Uani 1 1 d . . . C14 C 0.3278(3) 0.7454(12) 0.4761(2) 0.060(2) Uani 1 1 d . . . H4 H 0.3650 0.7239 0.4984 0.072 Uiso 1 1 calc R . . C11 C -0.1363(3) 0.7820(11) 0.53600(18) 0.0514(18) Uani 1 1 d . . . H9 H -0.1408 0.8131 0.5640 0.062 Uiso 1 1 calc R . . C13 C -0.1876(3) 0.7003(10) 0.46480(19) 0.0496(17) Uani 1 1 d . . . H7 H -0.2263 0.6727 0.4441 0.059 Uiso 1 1 calc R . . C12 C -0.1946(3) 0.7437(11) 0.50572(19) 0.0556(19) Uani 1 1 d . . . H8 H -0.2379 0.7476 0.5132 0.067 Uiso 1 1 calc R . . C35 C -0.2275(3) 0.1964(11) 0.26369(19) 0.058(2) Uani 1 1 d . . . H28 H -0.2475 0.1944 0.2346 0.070 Uiso 1 1 calc R . . C33 C -0.2384(3) 0.2184(11) 0.33798(18) 0.0527(19) Uani 1 1 d . . . H30 H -0.2664 0.2337 0.3584 0.063 Uiso 1 1 calc R . . C34 C -0.2676(4) 0.2166(15) 0.2947(2) 0.081(3) Uani 1 1 d . . . H29 H -0.3150 0.2293 0.2864 0.097 Uiso 1 1 calc R . . S2 S 0.38507(7) 0.0559(3) 0.09771(5) 0.0560(6) Uani 1 1 d . . . O8 O 0.19874(19) 0.2083(7) 0.13008(11) 0.0485(12) Uani 1 1 d . . . N6 N 0.1188(2) 0.1906(7) 0.18662(14) 0.0304(11) Uani 1 1 d . . . O7 O 0.3706(2) 0.1510(9) 0.22789(12) 0.0682(16) Uani 1 1 d . . . N4 N 0.3289(2) 0.2075(10) 0.11070(15) 0.0558(17) Uani 1 1 d . . . O5 O 0.3628(2) -0.1388(7) 0.10406(13) 0.0564(13) Uani 1 1 d . . . O6 O 0.3976(2) 0.1106(8) 0.05578(12) 0.0605(14) Uani 1 1 d . . . C26 C 0.1733(3) 0.1724(9) 0.25985(17) 0.0372(14) Uani 1 1 d . . . H20 H 0.2132 0.1688 0.2808 0.045 Uiso 1 1 calc R . . N5 N 0.2388(2) 0.1872(9) 0.20281(14) 0.0484(15) Uani 1 1 d . . . H15 H 0.2751 0.1855 0.2226 0.058 Uiso 1 1 calc R . . C18 C 0.5240(3) 0.1087(12) 0.12704(19) 0.058(2) Uani 1 1 d . . . H14 H 0.5303 0.0804 0.0992 0.069 Uiso 1 1 calc R . . C20 C 0.4469(3) 0.1590(12) 0.17808(18) 0.057(2) Uani 1 1 d . . . C24 C 0.2486(3) 0.1935(11) 0.16018(17) 0.0487(17) Uani 1 1 d . . . C30 C 0.3322(3) 0.4119(12) 0.0965(2) 0.062(2) Uani 1 1 d . . . H22 H 0.2903 0.4771 0.0993 0.092 Uiso 1 1 calc R . . H21 H 0.3378 0.4151 0.0670 0.092 Uiso 1 1 calc R . . H23 H 0.3705 0.4754 0.1142 0.092 Uiso 1 1 calc R . . C28 C 0.0500(3) 0.1790(11) 0.23986(18) 0.0532(19) Uani 1 1 d . . . H18 H 0.0068 0.1815 0.2477 0.064 Uiso 1 1 calc R . . C17 C 0.5801(3) 0.1474(12) 0.1590(2) 0.063(2) Uani 1 1 d . . . H13 H 0.6245 0.1404 0.1532 0.076 Uiso 1 1 calc R . . C27 C 0.1093(3) 0.1669(9) 0.27095(17) 0.0396(14) Uani 1 1 d . . . H19 H 0.1058 0.1549 0.2998 0.048 Uiso 1 1 calc R . . C23 C 0.3197(3) 0.1853(11) 0.15513(17) 0.0512(18) Uani 1 1 d . . . C25 C 0.1764(3) 0.1835(8) 0.21615(17) 0.0337(13) Uani 1 1 d . . . C22 C 0.3757(3) 0.1668(12) 0.18809(19) 0.060(2) Uani 1 1 d . . . C29 C 0.0562(3) 0.1872(10) 0.19763(18) 0.0484(17) Uani 1 1 d . . . H17 H 0.0169 0.1904 0.1763 0.058 Uiso 1 1 calc R . . C21 C 0.5038(3) 0.1976(13) 0.2096(2) 0.068(2) Uani 1 1 d . . . H11 H 0.4981 0.2247 0.2376 0.082 Uiso 1 1 calc R . . C19 C 0.4578(3) 0.1120(12) 0.13637(19) 0.056(2) Uani 1 1 d . . . C16 C 0.5697(3) 0.1964(14) 0.1997(2) 0.076(3) Uani 1 1 d . . . H12 H 0.6073 0.2291 0.2209 0.091 Uiso 1 1 calc R . . Cl2 Cl 0.28386(8) 0.3245(3) 0.38665(5) 0.0655(6) Uani 1 1 d . . . O12 O 0.4291(2) 0.1792(8) 0.30677(13) 0.0550(14) Uani 1 1 d . . . O11 O 0.3241(2) 0.0853(8) 0.31563(13) 0.0574(13) Uani 1 1 d . . . C42 C 0.4757(3) 0.1184(12) 0.39464(19) 0.060(2) Uani 1 1 d . . . H35 H 0.5038 0.0697 0.3766 0.072 Uiso 1 1 calc R . . C41 C 0.5020(3) 0.1374(13) 0.43826(19) 0.066(2) Uani 1 1 d . . . H34 H 0.5468 0.0989 0.4495 0.079 Uiso 1 1 calc R . . C39 C 0.3942(3) 0.2741(13) 0.44845(19) 0.064(2) Uani 1 1 d . . . H32 H 0.3674 0.3308 0.4664 0.076 Uiso 1 1 calc R . . C43 C 0.4086(3) 0.1701(11) 0.37729(18) 0.0514(18) Uani 1 1 d . . . C40 C 0.4604(3) 0.2148(13) 0.4650(2) 0.072(2) Uani 1 1 d . . . H33 H 0.4774 0.2266 0.4944 0.086 Uiso 1 1 calc R . . C44 C 0.3815(3) 0.1425(11) 0.33032(18) 0.0477(17) Uani 1 1 d . . . C38 C 0.3680(3) 0.2490(12) 0.40540(19) 0.0563(19) 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 C15 0.041(3) 0.080(5) 0.033(3) -0.004(3) 0.015(3) -0.009(3) S1 0.0280(7) 0.0872(13) 0.0182(7) 0.0024(7) 0.0094(5) 0.0024(7) Cl1 0.0298(8) 0.1150(16) 0.0346(8) -0.0162(9) 0.0174(6) -0.0077(8) O2 0.039(2) 0.074(3) 0.026(2) 0.0061(19) 0.0101(17) 0.004(2) O4 0.022(2) 0.104(4) 0.021(2) -0.006(2) 0.0056(16) 0.000(2) N3 0.023(2) 0.074(4) 0.023(2) -0.003(2) 0.0089(18) -0.003(2) O3 0.027(2) 0.090(3) 0.0190(19) 0.0035(19) 0.0093(15) -0.003(2) N1 0.024(2) 0.071(4) 0.022(2) 0.000(2) 0.0116(18) 0.000(2) O1 0.035(2) 0.106(4) 0.0196(19) -0.005(2) 0.0169(17) 0.004(2) N2 0.024(2) 0.070(4) 0.017(2) -0.002(2) 0.0060(17) -0.007(2) O10 0.027(3) 0.402(13) 0.029(3) -0.024(5) 0.010(2) 0.019(5) C8 0.031(3) 0.059(4) 0.027(3) 0.005(3) 0.014(2) 0.001(3) C37 0.032(3) 0.048(4) 0.026(3) 0.000(2) 0.009(2) -0.002(2) C3 0.028(3) 0.110(6) 0.032(3) 0.004(3) 0.013(3) -0.001(3) O9 0.025(2) 0.198(7) 0.020(2) -0.004(3) 0.0108(18) -0.006(3) C5 0.026(3) 0.090(5) 0.022(3) 0.006(3) 0.009(2) 0.001(3) C31 0.022(3) 0.077(5) 0.025(3) -0.008(3) 0.010(2) -0.005(3) C32 0.033(3) 0.049(4) 0.018(2) 0.001(2) 0.008(2) 0.002(2) C7 0.028(3) 0.088(5) 0.017(3) 0.002(3) 0.010(2) -0.004(3) C36 0.046(4) 0.055(4) 0.028(3) 0.001(3) 0.016(3) -0.004(3) C6 0.029(3) 0.077(5) 0.024(3) 0.005(3) 0.012(2) 0.000(3) C9 0.027(3) 0.048(4) 0.026(3) -0.003(2) 0.014(2) 0.000(2) C2 0.022(3) 0.144(7) 0.028(3) 0.007(4) 0.011(2) -0.003(4) C1 0.025(3) 0.103(6) 0.026(3) 0.005(3) 0.007(2) 0.001(3) C10 0.029(3) 0.064(4) 0.026(3) -0.003(3) 0.010(2) -0.001(3) C4 0.027(3) 0.087(5) 0.021(3) 0.003(3) 0.009(2) 0.000(3) C14 0.029(3) 0.120(7) 0.032(3) 0.010(4) 0.011(3) -0.002(3) C11 0.035(3) 0.100(6) 0.023(3) -0.005(3) 0.015(2) 0.009(3) C13 0.026(3) 0.094(5) 0.031(3) 0.004(3) 0.011(2) -0.005(3) C12 0.023(3) 0.117(6) 0.031(3) -0.006(3) 0.014(2) -0.005(3) C35 0.050(4) 0.107(6) 0.019(3) -0.001(3) 0.008(3) 0.009(4) C33 0.031(3) 0.105(6) 0.023(3) 0.003(3) 0.007(2) 0.013(3) C34 0.036(4) 0.178(9) 0.027(3) 0.002(4) 0.005(3) 0.024(5) S2 0.0249(7) 0.1221(17) 0.0238(7) 0.0011(9) 0.0117(6) 0.0046(9) O8 0.024(2) 0.105(4) 0.0177(19) 0.005(2) 0.0078(15) 0.004(2) N6 0.020(2) 0.054(3) 0.018(2) 0.000(2) 0.0056(17) 0.0009(19) O7 0.028(2) 0.160(5) 0.018(2) 0.001(2) 0.0091(17) 0.006(3) N4 0.021(2) 0.126(5) 0.023(2) 0.006(3) 0.0097(19) 0.014(3) O5 0.035(2) 0.098(4) 0.040(3) 0.002(2) 0.0159(19) -0.007(2) O6 0.036(2) 0.128(4) 0.021(2) 0.004(2) 0.0133(18) 0.006(2) C26 0.030(3) 0.062(4) 0.020(3) -0.001(3) 0.006(2) 0.006(3) N5 0.021(2) 0.111(5) 0.014(2) 0.005(2) 0.0045(17) 0.007(3) C18 0.029(3) 0.119(7) 0.029(3) 0.000(3) 0.013(3) 0.006(3) C20 0.027(3) 0.125(7) 0.019(3) 0.004(3) 0.006(2) 0.008(3) C24 0.028(3) 0.102(6) 0.020(3) 0.003(3) 0.012(2) 0.001(3) C30 0.048(4) 0.112(7) 0.029(3) 0.015(4) 0.019(3) 0.014(4) C28 0.026(3) 0.110(6) 0.027(3) -0.003(3) 0.012(2) 0.002(3) C17 0.021(3) 0.136(7) 0.034(3) -0.001(4) 0.011(3) 0.002(3) C27 0.037(3) 0.065(4) 0.019(3) 0.002(3) 0.012(2) 0.001(3) C23 0.022(3) 0.117(6) 0.016(3) 0.001(3) 0.006(2) 0.001(3) C25 0.026(3) 0.049(4) 0.029(3) -0.001(2) 0.013(2) 0.002(2) C22 0.029(3) 0.130(7) 0.023(3) -0.003(3) 0.013(2) 0.002(4) C29 0.023(3) 0.097(5) 0.027(3) -0.003(3) 0.010(2) 0.000(3) C21 0.024(3) 0.155(8) 0.027(3) -0.006(4) 0.005(3) 0.003(4) C19 0.024(3) 0.120(7) 0.025(3) 0.002(3) 0.006(2) 0.002(3) C16 0.021(3) 0.173(9) 0.034(4) -0.001(4) 0.007(3) 0.000(4) Cl2 0.0251(8) 0.1290(18) 0.0450(9) -0.0002(10) 0.0132(7) 0.0000(9) O12 0.027(2) 0.118(4) 0.022(2) -0.007(2) 0.0118(17) -0.020(2) O11 0.024(2) 0.118(4) 0.030(2) 0.008(2) 0.0055(17) -0.010(2) C42 0.026(3) 0.129(7) 0.027(3) -0.005(3) 0.008(2) 0.003(3) C41 0.024(3) 0.148(8) 0.026(3) -0.008(4) 0.001(2) 0.006(4) C39 0.027(3) 0.140(7) 0.026(3) -0.001(4) 0.011(2) 0.002(4) C43 0.024(3) 0.110(6) 0.023(3) 0.004(3) 0.010(2) 0.000(3) C40 0.041(4) 0.147(8) 0.030(3) -0.006(4) 0.012(3) -0.005(4) C44 0.023(3) 0.097(5) 0.024(3) 0.002(3) 0.006(2) -0.006(3) C38 0.030(3) 0.113(6) 0.029(3) 0.004(3) 0.012(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 C15 N3 1.460(8) . ? C15 H26 0.9600 . ? C15 H25 0.9600 . ? C15 H24 0.9600 . ? S1 O1 1.435(4) . ? S1 O2 1.436(5) . ? S1 N3 1.636(5) . ? S1 C5 1.753(6) . ? Cl1 C37 1.725(6) . ? O4 C8 1.235(7) . ? N3 C7 1.455(6) . ? O3 C6 1.282(6) . ? N1 C9 1.370(6) . ? N1 C8 1.383(6) . ? N1 H5 0.8600 . ? N2 C9 1.340(7) . ? N2 C13 1.357(6) . ? N2 H6 0.94(7) . ? O10 C31 1.156(7) . ? C8 C7 1.450(7) . ? C37 C36 1.380(8) . ? C37 C32 1.401(6) . ? C3 C2 1.383(9) . ? C3 C5 1.401(7) . ? C3 H3 0.9300 . ? O9 C31 1.291(6) . ? O9 H31 0.98(8) . ? C5 C4 1.406(7) . ? C31 C32 1.480(7) . ? C32 C33 1.387(8) . ? C7 C6 1.384(8) . ? C36 C35 1.386(8) . ? C36 H27 0.9300 . ? C6 C4 1.491(7) . ? C9 C10 1.402(7) . ? C2 C14 1.386(8) . ? C2 H2 0.9300 . ? C1 C14 1.388(7) . ? C1 C4 1.394(8) . ? C1 H1 0.9300 . ? C10 C11 1.373(7) . ? C10 H10 0.9300 . ? C14 H4 0.9300 . ? C11 C12 1.379(8) . ? C11 H9 0.9300 . ? C13 C12 1.357(8) . ? C13 H7 0.9300 . ? C12 H8 0.9300 . ? C35 C34 1.376(8) . ? C35 H28 0.9300 . ? C33 C34 1.381(9) . ? C33 H30 0.9300 . ? C34 H29 0.9300 . ? S2 O6 1.441(4) . ? S2 O5 1.442(5) . ? S2 N4 1.634(5) . ? S2 C19 1.748(6) . ? O8 C24 1.240(7) . ? N6 C25 1.332(7) . ? N6 C29 1.347(6) . ? N6 H16 0.85(7) . ? O7 C22 1.283(6) . ? N4 C23 1.455(6) . ? N4 C30 1.488(9) . ? C26 C27 1.374(7) . ? C26 C25 1.394(7) . ? C26 H20 0.9300 . ? N5 C25 1.374(6) . ? N5 C24 1.396(6) . ? N5 H15 0.8600 . ? C18 C17 1.381(9) . ? C18 C19 1.394(7) . ? C18 H14 0.9300 . ? C20 C21 1.383(9) . ? C20 C19 1.411(8) . ? C20 C22 1.500(8) . ? C24 C23 1.444(7) . ? C30 H22 0.9600 . ? C30 H21 0.9600 . ? C30 H23 0.9600 . ? C28 C29 1.362(7) . ? C28 C27 1.386(8) . ? C28 H18 0.9300 . ? C17 C16 1.381(8) . ? C17 H13 0.9300 . ? C27 H19 0.9300 . ? C23 C22 1.377(8) . ? C29 H17 0.9300 . ? C21 C16 1.394(8) . ? C21 H11 0.9300 . ? C16 H12 0.9300 . ? Cl2 C38 1.739(7) . ? O12 C44 1.327(6) . ? O12 H36 0.90(6) . ? O11 C44 1.209(7) . ? C42 C43 1.384(8) . ? C42 C41 1.385(8) . ? C42 H35 0.9300 . ? C41 C40 1.390(9) . ? C41 H34 0.9300 . ? C39 C38 1.372(8) . ? C39 C40 1.378(9) . ? C39 H32 0.9300 . ? C43 C38 1.413(8) . ? C43 C44 1.492(8) . ? C40 H33 0.9300 . ? 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 N3 C15 H26 109.5 . . ? N3 C15 H25 109.5 . . ? H26 C15 H25 109.5 . . ? N3 C15 H24 109.5 . . ? H26 C15 H24 109.5 . . ? H25 C15 H24 109.5 . . ? O1 S1 O2 118.4(3) . . ? O1 S1 N3 107.6(3) . . ? O2 S1 N3 108.3(3) . . ? O1 S1 C5 109.6(3) . . ? O2 S1 C5 109.1(3) . . ? N3 S1 C5 102.5(3) . . ? C7 N3 C15 115.1(5) . . ? C7 N3 S1 113.0(4) . . ? C15 N3 S1 116.1(3) . . ? C9 N1 C8 126.0(5) . . ? C9 N1 H5 117.0 . . ? C8 N1 H5 117.0 . . ? C9 N2 C13 122.0(5) . . ? C9 N2 H6 117(4) . . ? C13 N2 H6 120(4) . . ? O4 C8 N1 121.6(5) . . ? O4 C8 C7 124.3(5) . . ? N1 C8 C7 114.1(5) . . ? C36 C37 C32 121.0(5) . . ? C36 C37 Cl1 116.9(4) . . ? C32 C37 Cl1 122.1(4) . . ? C2 C3 C5 118.2(5) . . ? C2 C3 H3 120.9 . . ? C5 C3 H3 120.9 . . ? C31 O9 H31 106(4) . . ? C3 C5 C4 122.1(5) . . ? C3 C5 S1 120.5(4) . . ? C4 C5 S1 117.4(4) . . ? O10 C31 O9 119.2(5) . . ? O10 C31 C32 126.7(5) . . ? O9 C31 C32 114.0(5) . . ? C33 C32 C37 117.8(5) . . ? C33 C32 C31 119.0(4) . . ? C37 C32 C31 123.3(5) . . ? C6 C7 C8 125.0(5) . . ? C6 C7 N3 121.3(4) . . ? C8 C7 N3 113.7(5) . . ? C37 C36 C35 120.4(5) . . ? C37 C36 H27 119.8 . . ? C35 C36 H27 119.8 . . ? O3 C6 C7 122.9(5) . . ? O3 C6 C4 117.5(5) . . ? C7 C6 C4 119.6(5) . . ? N2 C9 N1 119.8(5) . . ? N2 C9 C10 119.8(4) . . ? N1 C9 C10 120.3(5) . . ? C3 C2 C14 120.7(5) . . ? C3 C2 H2 119.7 . . ? C14 C2 H2 119.7 . . ? C14 C1 C4 120.3(5) . . ? C14 C1 H1 119.9 . . ? C4 C1 H1 119.9 . . ? C11 C10 C9 117.4(5) . . ? C11 C10 H10 121.3 . . ? C9 C10 H10 121.3 . . ? C1 C4 C5 117.9(5) . . ? C1 C4 C6 120.1(5) . . ? C5 C4 C6 121.9(5) . . ? C2 C14 C1 120.9(6) . . ? C2 C14 H4 119.6 . . ? C1 C14 H4 119.6 . . ? C10 C11 C12 121.8(5) . . ? C10 C11 H9 119.1 . . ? C12 C11 H9 119.1 . . ? N2 C13 C12 120.0(6) . . ? N2 C13 H7 120.0 . . ? C12 C13 H7 120.0 . . ? C13 C12 C11 118.8(5) . . ? C13 C12 H8 120.6 . . ? C11 C12 H8 120.6 . . ? C34 C35 C36 119.0(6) . . ? C34 C35 H28 120.5 . . ? C36 C35 H28 120.5 . . ? C34 C33 C32 121.0(5) . . ? C34 C33 H30 119.5 . . ? C32 C33 H30 119.5 . . ? C35 C34 C33 120.9(6) . . ? C35 C34 H29 119.5 . . ? C33 C34 H29 119.5 . . ? O6 S2 O5 118.8(3) . . ? O6 S2 N4 107.6(3) . . ? O5 S2 N4 109.0(3) . . ? O6 S2 C19 108.9(3) . . ? O5 S2 C19 110.1(3) . . ? N4 S2 C19 101.0(3) . . ? C25 N6 C29 121.8(5) . . ? C25 N6 H16 124(5) . . ? C29 N6 H16 114(5) . . ? C23 N4 C30 114.2(5) . . ? C23 N4 S2 112.7(4) . . ? C30 N4 S2 117.7(4) . . ? C27 C26 C25 117.7(5) . . ? C27 C26 H20 121.1 . . ? C25 C26 H20 121.1 . . ? C25 N5 C24 126.1(5) . . ? C25 N5 H15 116.9 . . ? C24 N5 H15 116.9 . . ? C17 C18 C19 120.1(5) . . ? C17 C18 H14 120.0 . . ? C19 C18 H14 120.0 . . ? C21 C20 C19 118.1(5) . . ? C21 C20 C22 120.8(5) . . ? C19 C20 C22 121.1(5) . . ? O8 C24 N5 120.5(5) . . ? O8 C24 C23 124.8(5) . . ? N5 C24 C23 114.7(5) . . ? N4 C30 H22 109.5 . . ? N4 C30 H21 109.5 . . ? H22 C30 H21 109.5 . . ? N4 C30 H23 109.5 . . ? H22 C30 H23 109.5 . . ? H21 C30 H23 109.5 . . ? C29 C28 C27 118.5(5) . . ? C29 C28 H18 120.8 . . ? C27 C28 H18 120.8 . . ? C18 C17 C16 119.4(5) . . ? C18 C17 H13 120.3 . . ? C16 C17 H13 120.3 . . ? C26 C27 C28 121.1(5) . . ? C26 C27 H19 119.4 . . ? C28 C27 H19 119.4 . . ? C22 C23 C24 125.6(5) . . ? C22 C23 N4 120.7(5) . . ? C24 C23 N4 113.6(5) . . ? N6 C25 N5 119.0(5) . . ? N6 C25 C26 120.3(4) . . ? N5 C25 C26 120.7(5) . . ? O7 C22 C23 123.4(5) . . ? O7 C22 C20 116.7(5) . . ? C23 C22 C20 119.9(5) . . ? N6 C29 C28 120.5(5) . . ? N6 C29 H17 119.8 . . ? C28 C29 H17 119.8 . . ? C20 C21 C16 120.6(6) . . ? C20 C21 H11 119.7 . . ? C16 C21 H11 119.7 . . ? C18 C19 C20 120.8(6) . . ? C18 C19 S2 122.1(5) . . ? C20 C19 S2 117.0(4) . . ? C17 C16 C21 121.0(6) . . ? C17 C16 H12 119.5 . . ? C21 C16 H12 119.5 . . ? C44 O12 H36 108(4) . . ? C43 C42 C41 121.6(6) . . ? C43 C42 H35 119.2 . . ? C41 C42 H35 119.2 . . ? C42 C41 C40 119.1(6) . . ? C42 C41 H34 120.5 . . ? C40 C41 H34 120.5 . . ? C38 C39 C40 119.7(6) . . ? C38 C39 H32 120.1 . . ? C40 C39 H32 120.1 . . ? C42 C43 C38 117.8(6) . . ? C42 C43 C44 120.1(5) . . ? C38 C43 C44 122.1(5) . . ? C39 C40 C41 120.7(6) . . ? C39 C40 H33 119.6 . . ? C41 C40 H33 119.6 . . ? O11 C44 O12 124.0(5) . . ? O11 C44 C43 124.2(5) . . ? O12 C44 C43 111.7(5) . . ? C39 C38 C43 121.1(6) . . ? C39 C38 Cl2 117.4(5) . . ? C43 C38 Cl2 121.5(5) . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 26.68 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.758 _refine_diff_density_min -0.688 _refine_diff_density_rms 0.099 # Attachment 'PXZ 2FBA.cif' data_shelxl_PXZ_2FBA _database_code_depnum_ccdc_archive 'CCDC 890557' #TrackingRef 'PXZ 2FBA.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H13 N3 O4 S, C7 H5 F O2' _chemical_formula_sum 'C22 H18 F N3 O6 S' _chemical_formula_weight 471.45 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' F F 0.0171 0.0103 '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 P21/c 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 10.8016(3) _cell_length_b 20.9659(6) _cell_length_c 9.2105(2) _cell_angle_alpha 90.00 _cell_angle_beta 95.787(2) _cell_angle_gamma 90.00 _cell_volume 2075.23(9) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 27224 _cell_measurement_theta_min 1 _cell_measurement_theta_max 25.35 _exptl_crystal_description Needles _exptl_crystal_colour yellow _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.509 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 976 _exptl_absorpt_coefficient_mu 0.212 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8096 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'SADABS (Blessing, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 KappaCCD _diffrn_measurement_method 'CCD; rotation images' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26715 _diffrn_reflns_av_R_equivalents 0.0959 _diffrn_reflns_av_sigmaI/netI 0.0530 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 25.36 _reflns_number_total 3776 _reflns_number_gt 2649 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo&Scalepack (Otwinowski,Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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. Disorder refinement details: The disordered benzene ring of the 2-fluorobenzoic acid molecule has two possible positions which are too close to each other to allow a well-behaved anisotropic refinement. The isotropic displacement parameters of the corresponding carbon atoms of each benzene carbon were therefore constrained to be equal and the two sites allowed to refine freely against each other to a 60:40 occupancy. Attempts to model two positions for the carboxylic acid group on the 2-fluorobenzoic acid resulted in an increased R-factor. Single positions for this group were therefore chosen as the best representation of the data. This was further supported by the well-behaved anisotropic displacement parameters (ADPs) of the carboxylic acid group. Hydrogen refinement details: Hydrogen atoms not involved in HBs were placed on calculated positions and refined as riding on the atoms to which they were bonded. The H-atoms involved in HBs were then identified using Fourier difference maps. Problem: PLAT201_ALERT_2_B Isotropic non-H Atoms in Main Residue(s) ....... 7 Response: Overlap of two disordered ring positions means a meaningful anisotropic refinement could not be performed Problem: PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds ...............0.0044 Ang Response: Poorly diffracting needle shaped crystals resulted in poor resolution of data ; _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^)+(0.0430P)^2^+2.4905P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3776 _refine_ls_number_parameters 286 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0927 _refine_ls_R_factor_gt 0.0568 _refine_ls_wR_factor_ref 0.1325 _refine_ls_wR_factor_gt 0.1170 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _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 H4 H 0.765(4) 0.029(2) 0.680(5) 0.086(16) Uiso 1 1 d . . . H16 H 0.459(3) 0.0360(16) 0.875(4) 0.044(10) Uiso 1 1 d . . . H17 H 0.417(3) 0.0819(15) 1.001(3) 0.031(9) Uiso 1 1 d . . . H15 H 0.341(3) 0.0177(17) 0.980(4) 0.043(10) Uiso 1 1 d . . . H14 H -0.044(3) -0.0461(18) 0.881(4) 0.050(11) Uiso 1 1 d . . . H9 H 0.109(3) -0.0393(17) 0.595(4) 0.043(11) Uiso 1 1 d . . . S1 S 0.32657(8) 0.15583(4) 0.77235(8) 0.0340(2) Uani 1 1 d . . . O6 O 0.0936(2) 0.01364(10) 0.8945(2) 0.0319(5) Uani 1 1 d . . . N2 N 0.0764(3) -0.03856(12) 0.6747(3) 0.0299(6) Uani 1 1 d . . . O5 O 0.2213(2) 0.00313(10) 0.4836(2) 0.0344(5) Uani 1 1 d . . . O3 O 0.4026(2) 0.18840(11) 0.8855(2) 0.0444(6) Uani 1 1 d . . . N3 N -0.0687(2) -0.07653(12) 0.8271(3) 0.0283(6) Uani 1 1 d . . . O4 O 0.2136(2) 0.18545(10) 0.7110(2) 0.0385(6) Uani 1 1 d . . . C14 C 0.2712(3) 0.04049(14) 0.5831(3) 0.0294(7) Uani 1 1 d . . . N1 N 0.2907(2) 0.08556(12) 0.8322(3) 0.0295(6) Uani 1 1 d . . . C18 C -0.0584(3) -0.12806(14) 0.6020(3) 0.0303(7) Uani 1 1 d . . . H18 H -0.0238 -0.1326 0.5141 0.036 Uiso 1 1 calc R . . C16 C 0.1297(3) 0.00725(14) 0.7713(3) 0.0285(7) Uani 1 1 d . . . C12 C 0.3783(3) 0.08106(14) 0.5473(3) 0.0309(7) Uani 1 1 d . . . C17 C -0.0157(3) -0.08028(14) 0.7011(3) 0.0275(7) Uani 1 1 d . . . C15 C 0.2300(3) 0.04419(13) 0.7209(3) 0.0266(7) Uani 1 1 d . . . C21 C -0.1613(3) -0.11552(14) 0.8617(3) 0.0313(7) Uani 1 1 d . . . H21 H -0.1950 -0.1106 0.9500 0.038 Uiso 1 1 calc R . . C10 C 0.5472(3) 0.10189(17) 0.3997(4) 0.0430(9) Uani 1 1 d . . . H10 H 0.5914 0.0904 0.3222 0.052 Uiso 1 1 calc R . . C22 C 0.3856(4) 0.05256(18) 0.9325(4) 0.0361(8) Uani 1 1 d . . . C19 C -0.1517(3) -0.16805(14) 0.6357(3) 0.0311(7) Uani 1 1 d . . . H19 H -0.1801 -0.1998 0.5701 0.037 Uiso 1 1 calc R . . C11 C 0.4446(3) 0.06601(16) 0.4294(3) 0.0359(8) Uani 1 1 d . . . H11 H 0.4198 0.0315 0.3701 0.043 Uiso 1 1 calc R . . C8 C 0.5188(4) 0.17163(17) 0.5992(4) 0.0458(9) Uani 1 1 d . . . H8 H 0.5428 0.2070 0.6560 0.055 Uiso 1 1 calc R . . C13 C 0.4165(3) 0.13539(15) 0.6295(3) 0.0356(8) Uani 1 1 d . . . C20 C -0.2048(3) -0.16189(15) 0.7667(3) 0.0322(7) Uani 1 1 d . . . H20 H -0.2685 -0.1889 0.7888 0.039 Uiso 1 1 calc R . . C9 C 0.5843(4) 0.15449(18) 0.4840(4) 0.0491(10) Uani 1 1 d . . . H9A H 0.6531 0.1782 0.4630 0.059 Uiso 1 1 calc R . . O2 O 0.7588(2) 0.04914(11) 0.7651(2) 0.0397(6) Uani 1 1 d . A . O1 O 0.9002(2) 0.11269(12) 0.6757(2) 0.0462(6) Uani 1 1 d . A . C7 C 0.8339(3) 0.09908(15) 0.7698(3) 0.0310(7) Uani 1 1 d . . . F1A F 1.0146(5) 0.1874(2) 0.8921(5) 0.0477(16) Uiso 0.394(5) 1 d P A 1 C1A C 0.7078(5) 0.1394(3) 0.9732(7) 0.0298(9) Uiso 0.394(5) 1 d PG A 1 H1A H 0.6444 0.1118 0.9374 0.036 Uiso 0.394(5) 1 calc PR A 1 C2A C 0.6932(5) 0.1772(3) 1.0941(6) 0.0325(10) Uiso 0.394(5) 1 d PG A 1 H2A H 0.6200 0.1750 1.1392 0.039 Uiso 0.394(5) 1 calc PR A 1 C3A C 0.7878(6) 0.2184(3) 1.1476(5) 0.0286(10) Uiso 0.394(5) 1 d PG A 1 H3A H 0.7780 0.2438 1.2285 0.034 Uiso 0.394(5) 1 calc PR A 1 C4A C 0.8971(5) 0.2217(3) 1.0802(6) 0.0285(9) Uiso 0.394(5) 1 d PG A 1 H4A H 0.9605 0.2493 1.1160 0.034 Uiso 0.394(5) 1 calc PR A 1 C5A C 0.9117(5) 0.1838(3) 0.9592(7) 0.0300(9) Uiso 0.394(5) 1 d PG A 1 C6A C 0.8171(6) 0.1427(3) 0.9057(6) 0.0246(8) Uiso 0.394(5) 1 d PG A 1 F1B F 0.6458(3) 0.09691(15) 0.9719(3) 0.0447(11) Uiso 0.606(5) 1 d P A 2 C1B C 0.7411(3) 0.13672(17) 0.9951(4) 0.0298(9) Uiso 0.606(5) 1 d PG A 2 C2B C 0.7422(4) 0.17843(17) 1.1125(4) 0.0325(10) Uiso 0.606(5) 1 d PG A 2 H2B H 0.6781 0.1773 1.1728 0.039 Uiso 0.606(5) 1 calc PR A 2 C3B C 0.8390(4) 0.22183(16) 1.1398(3) 0.0286(10) Uiso 0.606(5) 1 d PG A 2 H3B H 0.8397 0.2497 1.2184 0.034 Uiso 0.606(5) 1 calc PR A 2 C4B C 0.9347(3) 0.22352(17) 1.0497(4) 0.0285(9) Uiso 0.606(5) 1 d PG A 2 H4B H 0.9995 0.2526 1.0680 0.034 Uiso 0.606(5) 1 calc PR A 2 C5B C 0.9336(3) 0.1818(2) 0.9323(4) 0.0300(9) Uiso 0.606(5) 1 d PG A 2 H5B H 0.9976 0.1829 0.8720 0.036 Uiso 0.606(5) 1 calc PR A 2 C6B C 0.8368(4) 0.1384(2) 0.9050(4) 0.0246(8) Uiso 0.606(5) 1 d PG A 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_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0489(5) 0.0244(4) 0.0284(4) -0.0039(3) 0.0023(4) -0.0060(4) O6 0.0409(13) 0.0293(12) 0.0252(11) -0.0043(9) 0.0009(9) -0.0063(10) N2 0.0379(16) 0.0248(14) 0.0264(15) -0.0029(11) -0.0004(12) -0.0028(12) O5 0.0446(14) 0.0285(12) 0.0293(11) -0.0067(9) 0.0001(10) -0.0011(10) O3 0.0603(16) 0.0373(13) 0.0354(13) -0.0081(10) 0.0037(11) -0.0201(12) N3 0.0380(16) 0.0200(14) 0.0257(14) -0.0023(11) -0.0036(12) -0.0009(12) O4 0.0575(16) 0.0249(12) 0.0326(12) -0.0022(9) 0.0020(11) 0.0050(11) C14 0.0372(19) 0.0208(15) 0.0285(16) -0.0015(13) -0.0050(14) 0.0051(14) N1 0.0359(15) 0.0240(14) 0.0269(13) -0.0020(11) -0.0054(11) -0.0033(12) C18 0.0393(19) 0.0236(16) 0.0272(16) -0.0025(13) -0.0012(14) 0.0031(15) C16 0.0354(18) 0.0215(16) 0.0268(16) -0.0023(13) -0.0060(14) 0.0009(14) C12 0.0390(19) 0.0222(16) 0.0307(17) 0.0020(13) -0.0011(14) 0.0008(14) C17 0.0336(18) 0.0211(15) 0.0260(16) 0.0014(12) -0.0051(13) 0.0020(14) C15 0.0343(18) 0.0191(15) 0.0248(15) -0.0030(12) -0.0040(13) -0.0011(13) C21 0.0368(19) 0.0277(17) 0.0290(17) 0.0012(13) 0.0013(14) 0.0003(15) C10 0.052(2) 0.041(2) 0.0368(19) 0.0034(16) 0.0097(17) -0.0002(18) C22 0.040(2) 0.035(2) 0.0306(18) 0.0004(16) -0.0105(17) -0.0035(17) C19 0.0385(19) 0.0245(17) 0.0284(16) -0.0037(13) -0.0052(14) -0.0022(14) C11 0.046(2) 0.0287(17) 0.0320(17) 0.0007(14) 0.0015(15) 0.0014(16) C8 0.060(2) 0.039(2) 0.039(2) -0.0023(16) 0.0068(18) -0.0173(19) C13 0.043(2) 0.0313(18) 0.0315(17) 0.0011(14) -0.0007(15) -0.0021(16) C20 0.0372(19) 0.0237(16) 0.0348(17) -0.0001(14) -0.0010(15) -0.0033(14) C9 0.055(2) 0.046(2) 0.048(2) 0.0035(18) 0.0120(19) -0.0162(19) O2 0.0623(17) 0.0301(13) 0.0273(12) -0.0046(10) 0.0067(11) -0.0106(12) O1 0.0549(17) 0.0539(16) 0.0314(13) -0.0057(11) 0.0118(12) -0.0084(13) C7 0.0358(19) 0.0291(17) 0.0270(16) 0.0046(14) -0.0018(14) 0.0014(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 O3 1.433(2) . ? S1 O4 1.433(2) . ? S1 N1 1.633(3) . ? S1 C13 1.765(3) . ? O6 C16 1.243(4) . ? N2 C17 1.365(4) . ? N2 C16 1.394(4) . ? N2 H9 0.85(4) . ? O5 C14 1.282(3) . ? N3 C17 1.347(4) . ? N3 C21 1.354(4) . ? N3 H14 0.84(4) . ? C14 C15 1.388(4) . ? C14 C12 1.499(5) . ? N1 C15 1.448(4) . ? N1 C22 1.481(4) . ? C18 C19 1.370(4) . ? C18 C17 1.402(4) . ? C18 H18 0.9300 . ? C16 C15 1.447(4) . ? C12 C11 1.395(5) . ? C12 C13 1.407(4) . ? C21 C20 1.359(4) . ? C21 H21 0.9300 . ? C10 C9 1.385(5) . ? C10 C11 1.389(5) . ? C10 H10 0.9300 . ? C22 H16 1.06(4) . ? C22 H17 0.92(3) . ? C22 H15 1.00(4) . ? C19 C20 1.393(4) . ? C19 H19 0.9300 . ? C11 H11 0.9300 . ? C8 C9 1.381(5) . ? C8 C13 1.393(5) . ? C8 H8 0.9300 . ? C20 H20 0.9300 . ? C9 H9A 0.9300 . ? O2 C7 1.323(4) . ? O2 H4 0.90(5) . ? O1 C7 1.213(4) . ? C7 C6B 1.491(4) . ? C7 C6A 1.575(5) . ? F1A C5A 1.327(7) . ? C1A C2A 1.3900 . ? C1A C6A 1.3900 . ? C1A H1A 0.9300 . ? C2A C3A 1.3900 . ? C2A H2A 0.9300 . ? C3A C4A 1.3900 . ? C3A H3A 0.9300 . ? C4A C5A 1.3900 . ? C4A H4A 0.9300 . ? C5A C6A 1.3900 . ? F1B C1B 1.325(4) . ? C1B C2B 1.3900 . ? C1B C6B 1.3900 . ? C2B C3B 1.3900 . ? C2B H2B 0.9300 . ? C3B C4B 1.3900 . ? C3B H3B 0.9300 . ? C4B C5B 1.3900 . ? C4B H4B 0.9300 . ? C5B C6B 1.3900 . ? C5B H5B 0.9300 . ? 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 O3 S1 O4 118.90(14) . . ? O3 S1 N1 108.83(13) . . ? O4 S1 N1 107.61(14) . . ? O3 S1 C13 109.83(15) . . ? O4 S1 C13 108.75(14) . . ? N1 S1 C13 101.50(14) . . ? C17 N2 C16 126.1(3) . . ? C17 N2 H9 121(2) . . ? C16 N2 H9 113(2) . . ? C17 N3 C21 123.7(3) . . ? C17 N3 H14 115(3) . . ? C21 N3 H14 121(3) . . ? O5 C14 C15 122.5(3) . . ? O5 C14 C12 117.8(3) . . ? C15 C14 C12 119.7(3) . . ? C15 N1 C22 113.4(2) . . ? C15 N1 S1 114.05(19) . . ? C22 N1 S1 117.3(2) . . ? C19 C18 C17 119.4(3) . . ? C19 C18 H18 120.3 . . ? C17 C18 H18 120.3 . . ? O6 C16 N2 120.7(3) . . ? O6 C16 C15 123.3(3) . . ? N2 C16 C15 116.0(3) . . ? C11 C12 C13 117.1(3) . . ? C11 C12 C14 120.7(3) . . ? C13 C12 C14 122.1(3) . . ? N3 C17 N2 119.8(3) . . ? N3 C17 C18 117.5(3) . . ? N2 C17 C18 122.7(3) . . ? C14 C15 C16 125.7(3) . . ? C14 C15 N1 121.1(3) . . ? C16 C15 N1 113.2(2) . . ? N3 C21 C20 119.7(3) . . ? N3 C21 H21 120.1 . . ? C20 C21 H21 120.1 . . ? C9 C10 C11 120.8(3) . . ? C9 C10 H10 119.6 . . ? C11 C10 H10 119.6 . . ? N1 C22 H16 110.4(18) . . ? N1 C22 H17 107.4(19) . . ? H16 C22 H17 109(3) . . ? N1 C22 H15 106.2(19) . . ? H16 C22 H15 113(3) . . ? H17 C22 H15 110(3) . . ? C18 C19 C20 121.0(3) . . ? C18 C19 H19 119.5 . . ? C20 C19 H19 119.5 . . ? C10 C11 C12 120.9(3) . . ? C10 C11 H11 119.6 . . ? C12 C11 H11 119.6 . . ? C9 C8 C13 119.4(3) . . ? C9 C8 H8 120.3 . . ? C13 C8 H8 120.3 . . ? C8 C13 C12 122.0(3) . . ? C8 C13 S1 121.6(3) . . ? C12 C13 S1 116.4(3) . . ? C21 C20 C19 118.6(3) . . ? C21 C20 H20 120.7 . . ? C19 C20 H20 120.7 . . ? C8 C9 C10 119.8(3) . . ? C8 C9 H9A 120.1 . . ? C10 C9 H9A 120.1 . . ? C7 O2 H4 107(3) . . ? O1 C7 O2 124.6(3) . . ? O1 C7 C6B 120.2(3) . . ? O2 C7 C6B 115.2(3) . . ? O1 C7 C6A 123.7(4) . . ? O2 C7 C6A 111.4(3) . . ? C2A C1A C6A 120.0 . . ? C2A C1A H1A 120.0 . . ? C6A C1A H1A 120.0 . . ? C3A C2A C1A 120.0 . . ? C3A C2A H2A 120.0 . . ? C1A C2A H2A 120.0 . . ? C4A C3A C2A 120.0 . . ? C4A C3A H3A 120.0 . . ? C2A C3A H3A 120.0 . . ? C3A C4A C5A 120.0 . . ? C3A C4A H4A 120.0 . . ? C5A C4A H4A 120.0 . . ? F1A C5A C6A 119.4(4) . . ? F1A C5A C4A 120.6(4) . . ? C6A C5A C4A 120.0 . . ? C5A C6A C1A 120.0 . . ? C5A C6A C7 120.2(4) . . ? C1A C6A C7 119.8(4) . . ? F1B C1B C2B 117.9(3) . . ? F1B C1B C6B 122.1(3) . . ? C2B C1B C6B 120.0 . . ? C3B C2B C1B 120.0 . . ? C3B C2B H2B 120.0 . . ? C1B C2B H2B 120.0 . . ? C2B C3B C4B 120.0 . . ? C2B C3B H3B 120.0 . . ? C4B C3B H3B 120.0 . . ? C5B C4B C3B 120.0 . . ? C5B C4B H4B 120.0 . . ? C3B C4B H4B 120.0 . . ? C4B C5B C6B 120.0 . . ? C4B C5B H5B 120.0 . . ? C6B C5B H5B 120.0 . . ? C5B C6B C1B 120.0 . . ? C5B C6B C7 117.7(3) . . ? C1B C6B C7 122.0(3) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.36 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.575 _refine_diff_density_min -0.486 _refine_diff_density_rms 0.056 # Attachment 'PXZ 2HBA.cif' data_shelxl_PXZ_2HB _database_code_depnum_ccdc_archive 'CCDC 890558' #TrackingRef 'PXZ 2HBA.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H13 N3 O4 S, C7 H6 O3' _chemical_formula_sum 'C22 H19 N3 O7 S' _chemical_formula_weight 469.46 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 P21/n 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 11.5454(5) _cell_length_b 9.2118(4) _cell_length_c 19.8419(9) _cell_angle_alpha 90.00 _cell_angle_beta 102.438(2) _cell_angle_gamma 90.00 _cell_volume 2060.73(16) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 68360 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.88 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.513 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 976 _exptl_absorpt_coefficient_mu 0.210 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7726 _exptl_absorpt_correction_T_max 1.0 _exptl_absorpt_process_details 'SADABS (Blessing, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 KappaCCD _diffrn_measurement_method 'CCD; rotation images' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20087 _diffrn_reflns_av_R_equivalents 0.1531 _diffrn_reflns_av_sigmaI/netI 0.1283 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 27.82 _reflns_number_total 4853 _reflns_number_gt 2639 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0342P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4853 _refine_ls_number_parameters 374 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1301 _refine_ls_R_factor_gt 0.0506 _refine_ls_wR_factor_ref 0.1044 _refine_ls_wR_factor_gt 0.0839 _refine_ls_goodness_of_fit_ref 0.956 _refine_ls_restrained_S_all 0.956 _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 H5 H 0.057(2) 0.139(3) 0.0277(12) 0.023(7) Uiso 1 1 d . . . H13 H 0.457(2) 0.503(3) -0.1242(13) 0.028(8) Uiso 1 1 d . . . H6 H 0.113(2) -0.006(3) 0.0747(14) 0.025(7) Uiso 1 1 d . . . H16 H 0.992(2) -0.120(3) 0.2107(12) 0.020(7) Uiso 1 1 d . . . H4 H 0.082(2) 0.628(3) 0.0336(13) 0.024(7) Uiso 1 1 d . . . H14 H 0.653(2) -0.152(3) 0.2313(13) 0.021(7) Uiso 1 1 d . . . H3 H -0.058(2) 0.705(3) 0.0997(13) 0.027(7) Uiso 1 1 d . . . H1 H 0.051(2) 0.351(3) 0.2158(14) 0.025(7) Uiso 1 1 d . . . H10 H 0.665(2) 0.066(3) -0.0981(13) 0.027(7) Uiso 1 1 d . . . H15 H 0.852(2) -0.233(3) 0.2554(14) 0.037(9) Uiso 1 1 d . . . H11 H 0.720(2) 0.249(3) -0.1750(13) 0.031(8) Uiso 1 1 d . . . H7 H 0.146(2) 0.042(3) 0.0016(14) 0.035(8) Uiso 1 1 d . . . H8 H 0.360(2) 0.410(3) -0.0380(14) 0.031(8) Uiso 1 1 d . . . H9 H 0.522(3) 0.119(3) -0.0469(15) 0.042(9) Uiso 1 1 d . . . H12 H 0.605(2) 0.465(3) -0.1844(13) 0.021(7) Uiso 1 1 d . . . H17 H 0.933(2) 0.083(3) 0.1353(13) 0.028(8) Uiso 1 1 d . . . H2 H -0.072(2) 0.563(3) 0.1973(14) 0.034(8) Uiso 1 1 d . . . H18 H 0.550(3) 0.128(4) 0.1361(18) 0.069(13) Uiso 1 1 d . . . H19 H 0.785(3) 0.338(4) 0.033(2) 0.096(14) Uiso 1 1 d . . . S1 S 0.22662(6) 0.21731(7) 0.15860(3) 0.02163(17) Uani 1 1 d . . . O4 O 0.39624(15) 0.09563(18) 0.00491(9) 0.0243(4) Uani 1 1 d . . . O1 O 0.25913(16) 0.51416(18) 0.00023(9) 0.0249(4) Uani 1 1 d . . . O3 O 0.34297(15) 0.26472(18) 0.19178(9) 0.0256(4) Uani 1 1 d . . . O2 O 0.16895(15) 0.10722(18) 0.19084(8) 0.0255(4) Uani 1 1 d . . . N3 N 0.5438(2) 0.1858(2) -0.07207(11) 0.0219(5) Uani 1 1 d . . . C10 C 0.3579(2) 0.2227(3) 0.00196(12) 0.0200(6) Uani 1 1 d . . . N2 N 0.3958(2) 0.3266(2) -0.03920(11) 0.0221(5) Uani 1 1 d . . . C8 C 0.2724(2) 0.2736(3) 0.03942(12) 0.0204(6) Uani 1 1 d . . . C4 C 0.1444(2) 0.4541(3) 0.08299(13) 0.0207(6) Uani 1 1 d . . . C7 C 0.2283(2) 0.4146(3) 0.03805(13) 0.0210(6) Uani 1 1 d . . . N1 N 0.23157(18) 0.1626(2) 0.08077(10) 0.0194(5) Uani 1 1 d . . . C14 C 0.6553(2) 0.2663(3) -0.15112(13) 0.0237(6) Uani 1 1 d . . . C3 C 0.1338(2) 0.3706(3) 0.14029(13) 0.0206(6) Uani 1 1 d . . . C11 C 0.4805(2) 0.3098(3) -0.07706(12) 0.0201(6) Uani 1 1 d . . . C15 C 0.6288(2) 0.1625(3) -0.10840(13) 0.0208(6) Uani 1 1 d . . . C13 C 0.5911(2) 0.3966(3) -0.15745(13) 0.0237(6) Uani 1 1 d . . . C5 C 0.0744(3) 0.5785(3) 0.06917(14) 0.0242(6) Uani 1 1 d . . . C2 C 0.0561(3) 0.4089(3) 0.18173(14) 0.0282(7) Uani 1 1 d . . . C9 C 0.1292(3) 0.0775(3) 0.04405(15) 0.0257(6) Uani 1 1 d . . . C6 C -0.0029(2) 0.6164(3) 0.11019(14) 0.0273(7) Uani 1 1 d . . . C12 C 0.5049(2) 0.4187(3) -0.12117(13) 0.0234(6) Uani 1 1 d . . . C1 C -0.0130(3) 0.5323(3) 0.16692(14) 0.0302(7) Uani 1 1 d . . . O6 O 0.56536(17) 0.0549(2) 0.16163(10) 0.0274(5) Uani 1 1 d . . . O5 O 0.62840(16) 0.26328(18) 0.08678(9) 0.0261(4) Uani 1 1 d . . . O7 O 0.80808(17) 0.2489(2) 0.06053(10) 0.0293(5) Uani 1 1 d . . . C20 C 0.8811(2) 0.0316(3) 0.15593(13) 0.0238(6) Uani 1 1 d . . . C18 C 0.8311(3) -0.1543(3) 0.22802(14) 0.0296(7) Uani 1 1 d . . . C21 C 0.7636(2) 0.0805(3) 0.14081(12) 0.0211(6) Uani 1 1 d . . . C16 C 0.6797(2) 0.0109(3) 0.17139(13) 0.0227(6) Uani 1 1 d . . . C22 C 0.7270(2) 0.2056(3) 0.09407(13) 0.0234(6) Uani 1 1 d . . . C19 C 0.9153(3) -0.0845(3) 0.19898(14) 0.0284(7) Uani 1 1 d . . . C17 C 0.7145(3) -0.1081(3) 0.21441(14) 0.0283(7) 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 0.0262(4) 0.0220(3) 0.0172(3) 0.0012(3) 0.0056(3) 0.0011(3) O4 0.0303(11) 0.0200(10) 0.0236(10) 0.0009(8) 0.0082(8) 0.0009(8) O1 0.0351(12) 0.0205(10) 0.0213(10) 0.0053(8) 0.0107(8) 0.0037(8) O3 0.0265(11) 0.0247(10) 0.0230(10) 0.0004(8) -0.0006(8) 0.0002(8) O2 0.0335(11) 0.0257(10) 0.0198(9) 0.0038(8) 0.0109(8) 0.0000(9) N3 0.0247(13) 0.0228(13) 0.0192(11) 0.0021(10) 0.0068(10) 0.0011(10) C10 0.0232(14) 0.0206(14) 0.0151(12) 0.0025(11) 0.0017(11) 0.0007(12) N2 0.0279(14) 0.0208(13) 0.0199(12) 0.0031(10) 0.0104(10) 0.0034(10) C8 0.0235(14) 0.0201(14) 0.0181(13) 0.0047(11) 0.0056(11) -0.0002(12) C4 0.0239(15) 0.0205(14) 0.0171(13) -0.0022(11) 0.0031(11) 0.0010(11) C7 0.0223(15) 0.0236(15) 0.0165(13) 0.0020(12) 0.0027(11) -0.0009(12) N1 0.0228(12) 0.0200(11) 0.0165(11) -0.0004(9) 0.0066(9) -0.0026(9) C14 0.0249(15) 0.0274(16) 0.0194(13) -0.0010(12) 0.0059(11) -0.0019(12) C3 0.0207(14) 0.0212(14) 0.0190(13) 0.0006(11) 0.0020(11) -0.0004(11) C11 0.0219(14) 0.0219(15) 0.0160(13) -0.0017(11) 0.0031(11) 0.0000(11) C15 0.0243(16) 0.0205(14) 0.0178(13) -0.0007(11) 0.0053(12) 0.0006(12) C13 0.0303(16) 0.0229(15) 0.0181(14) 0.0034(12) 0.0052(12) -0.0069(13) C5 0.0306(17) 0.0243(16) 0.0173(14) 0.0009(12) 0.0039(12) 0.0010(13) C2 0.0367(18) 0.0289(17) 0.0214(15) 0.0035(13) 0.0116(13) -0.0002(14) C9 0.0297(17) 0.0268(16) 0.0211(15) -0.0020(13) 0.0065(13) -0.0017(13) C6 0.0320(17) 0.0242(15) 0.0252(15) -0.0009(13) 0.0054(13) 0.0031(13) C12 0.0283(16) 0.0218(15) 0.0200(14) 0.0026(12) 0.0051(12) 0.0008(13) C1 0.0351(18) 0.0314(17) 0.0266(16) 0.0013(13) 0.0124(14) 0.0060(14) O6 0.0266(12) 0.0272(11) 0.0289(11) -0.0009(9) 0.0070(9) -0.0010(9) O5 0.0268(11) 0.0260(10) 0.0246(10) 0.0034(8) 0.0040(8) 0.0060(9) O7 0.0323(11) 0.0263(11) 0.0324(11) 0.0105(9) 0.0134(9) 0.0072(8) C20 0.0287(17) 0.0223(15) 0.0207(14) -0.0032(12) 0.0058(13) -0.0005(12) C18 0.047(2) 0.0219(16) 0.0199(14) 0.0029(12) 0.0068(14) 0.0046(14) C21 0.0275(16) 0.0194(14) 0.0159(13) -0.0016(11) 0.0038(11) 0.0023(12) C16 0.0275(16) 0.0210(14) 0.0183(13) -0.0044(11) 0.0021(11) -0.0018(12) C22 0.0292(16) 0.0206(14) 0.0200(13) -0.0022(11) 0.0041(12) -0.0019(13) C19 0.0343(18) 0.0268(16) 0.0216(15) -0.0022(12) 0.0002(13) 0.0074(14) C17 0.0401(19) 0.0227(15) 0.0245(15) 0.0010(13) 0.0124(14) -0.0001(14) _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 O3 1.4309(18) . ? S1 O2 1.4368(17) . ? S1 N1 1.637(2) . ? S1 C3 1.762(3) . ? O4 C10 1.248(3) . ? O1 C7 1.283(3) . ? N3 C11 1.349(3) . ? N3 C15 1.354(3) . ? N3 H9 0.87(3) . ? C10 N2 1.389(3) . ? C10 C8 1.436(3) . ? N2 C11 1.364(3) . ? N2 H8 0.88(3) . ? C8 C7 1.393(3) . ? C8 N1 1.452(3) . ? C4 C5 1.395(4) . ? C4 C3 1.400(3) . ? C4 C7 1.496(4) . ? N1 C9 1.473(3) . ? C14 C15 1.356(4) . ? C14 C13 1.403(4) . ? C14 H11 0.98(3) . ? C3 C2 1.387(4) . ? C11 C12 1.399(3) . ? C15 H10 0.98(2) . ? C13 C12 1.363(4) . ? C13 H12 0.86(2) . ? C5 C6 1.376(4) . ? C5 H4 0.86(3) . ? C2 C1 1.384(4) . ? C2 H1 0.87(3) . ? C9 H5 1.01(3) . ? C9 H6 1.03(3) . ? C9 H7 0.96(3) . ? C6 C1 1.392(4) . ? C6 H3 1.03(2) . ? C12 H13 0.95(3) . ? C1 H2 1.04(3) . ? O6 C16 1.355(3) . ? O6 H18 0.84(3) . ? O5 C22 1.237(3) . ? O7 C22 1.321(3) . ? O7 H19 0.99(4) . ? C20 C19 1.373(4) . ? C20 C21 1.399(4) . ? C20 H17 0.92(3) . ? C18 C17 1.383(4) . ? C18 C19 1.389(4) . ? C18 H15 0.90(3) . ? C21 C16 1.403(4) . ? C21 C22 1.482(3) . ? C16 C17 1.394(4) . ? C19 H16 0.93(2) . ? C17 H14 0.94(2) . ? 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 O3 S1 O2 119.33(10) . . ? O3 S1 N1 107.93(11) . . ? O2 S1 N1 108.45(10) . . ? O3 S1 C3 108.63(11) . . ? O2 S1 C3 109.73(12) . . ? N1 S1 C3 101.25(11) . . ? C11 N3 C15 122.6(2) . . ? C11 N3 H9 115.1(19) . . ? C15 N3 H9 122.1(19) . . ? O4 C10 N2 121.3(2) . . ? O4 C10 C8 124.0(2) . . ? N2 C10 C8 114.7(2) . . ? C11 N2 C10 126.9(2) . . ? C11 N2 H8 120.6(18) . . ? C10 N2 H8 112.5(18) . . ? C7 C8 C10 125.7(2) . . ? C7 C8 N1 120.4(2) . . ? C10 C8 N1 113.9(2) . . ? C5 C4 C3 117.6(2) . . ? C5 C4 C7 120.3(2) . . ? C3 C4 C7 122.1(2) . . ? O1 C7 C8 122.1(2) . . ? O1 C7 C4 118.1(2) . . ? C8 C7 C4 119.7(2) . . ? C8 N1 C9 114.8(2) . . ? C8 N1 S1 113.44(16) . . ? C9 N1 S1 116.29(17) . . ? C15 C14 C13 118.2(3) . . ? C15 C14 H11 119.2(15) . . ? C13 C14 H11 122.5(15) . . ? C2 C3 C4 121.5(2) . . ? C2 C3 S1 121.6(2) . . ? C4 C3 S1 116.9(2) . . ? N3 C11 N2 119.8(2) . . ? N3 C11 C12 118.3(3) . . ? N2 C11 C12 121.9(2) . . ? N3 C15 C14 120.6(3) . . ? N3 C15 H10 110.9(15) . . ? C14 C15 H10 128.6(15) . . ? C12 C13 C14 120.8(3) . . ? C12 C13 H12 118.6(17) . . ? C14 C13 H12 120.6(17) . . ? C6 C5 C4 121.0(3) . . ? C6 C5 H4 123.1(18) . . ? C4 C5 H4 116.0(18) . . ? C1 C2 C3 120.0(3) . . ? C1 C2 H1 122.2(17) . . ? C3 C2 H1 117.7(17) . . ? N1 C9 H5 112.4(14) . . ? N1 C9 H6 109.8(14) . . ? H5 C9 H6 111.6(19) . . ? N1 C9 H7 108.8(16) . . ? H5 C9 H7 103(2) . . ? H6 C9 H7 111(2) . . ? C5 C6 C1 121.0(3) . . ? C5 C6 H3 122.2(14) . . ? C1 C6 H3 116.8(14) . . ? C13 C12 C11 119.4(3) . . ? C13 C12 H13 124.9(16) . . ? C11 C12 H13 115.7(16) . . ? C2 C1 C6 119.0(3) . . ? C2 C1 H2 121.4(14) . . ? C6 C1 H2 119.6(14) . . ? C16 O6 H18 114(2) . . ? C22 O7 H19 113(2) . . ? C19 C20 C21 121.3(3) . . ? C19 C20 H17 123.0(17) . . ? C21 C20 H17 115.7(17) . . ? C17 C18 C19 121.0(3) . . ? C17 C18 H15 119.1(18) . . ? C19 C18 H15 119.8(18) . . ? C20 C21 C16 119.2(2) . . ? C20 C21 C22 121.1(2) . . ? C16 C21 C22 119.7(2) . . ? O6 C16 C17 117.8(2) . . ? O6 C16 C21 122.9(2) . . ? C17 C16 C21 119.3(2) . . ? O5 C22 O7 123.1(2) . . ? O5 C22 C21 122.5(2) . . ? O7 C22 C21 114.4(2) . . ? C20 C19 C18 119.1(3) . . ? C20 C19 H16 124.1(16) . . ? C18 C19 H16 116.9(15) . . ? C18 C17 C16 120.1(3) . . ? C18 C17 H14 125.1(15) . . ? C16 C17 H14 114.8(15) . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.82 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.286 _refine_diff_density_min -0.399 _refine_diff_density_rms 0.067 # Attachment 'PXZ 2NBA.cif' data_shelxl_PXZ_2NB _database_code_depnum_ccdc_archive 'CCDC 890559' #TrackingRef 'PXZ 2NBA.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H13 N3 O4 S, C7 H5 N O4' _chemical_formula_sum 'C22 H18 N4 O8 S' _chemical_formula_weight 498.46 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.0433(7) _cell_length_b 11.0546(8) _cell_length_c 13.8361(11) _cell_angle_alpha 99.6457(38) _cell_angle_beta 106.6493(41) _cell_angle_gamma 107.6305(42) _cell_volume 1078.84(15) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 25857 _cell_measurement_theta_min 1 _cell_measurement_theta_max 59.18 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.534 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 516 _exptl_absorpt_coefficient_mu 0.210 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9219 _exptl_absorpt_correction_T_max 1.0 _exptl_absorpt_process_details 'SADABS (Blessing, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'Bruker Apex II CCD' _diffrn_measurement_method 'CCD; rotation images' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25857 _diffrn_reflns_av_R_equivalents 0.0895 _diffrn_reflns_av_sigmaI/netI 0.0689 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.60 _diffrn_reflns_theta_max 29.51 _reflns_number_total 5764 _reflns_number_gt 4101 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2 (2009)' _computing_cell_refinement 'Bruker APEX2 (2009)' _computing_data_reduction 'Bruker APEX2 (2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _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^)+(0.0634P)^2^+0.1620P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5764 _refine_ls_number_parameters 388 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0834 _refine_ls_R_factor_gt 0.0519 _refine_ls_wR_factor_ref 0.1251 _refine_ls_wR_factor_gt 0.1120 _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_restrained_S_all 1.020 _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 H8 H 0.276(3) -0.136(2) 0.5592(17) 0.018(6) Uiso 1 1 d . . . H9 H 0.460(3) 0.071(2) 0.6611(17) 0.014(5) Uiso 1 1 d . . . H7 H 0.411(3) -0.284(2) 0.4983(18) 0.019(6) Uiso 1 1 d . . . H17 H 1.180(4) 0.013(2) 0.8675(18) 0.024(6) Uiso 1 1 d . . . H14 H 1.546(4) 0.767(2) 1.1170(18) 0.020(6) Uiso 1 1 d . . . H18 H 0.974(4) 0.011(2) 0.8588(18) 0.025(6) Uiso 1 1 d . . . H12 H 1.107(4) 0.870(2) 0.9912(18) 0.024(6) Uiso 1 1 d . . . H15 H 1.381(3) 0.568(2) 1.0116(18) 0.022(6) Uiso 1 1 d . . . H6 H 0.741(3) -0.201(2) 0.5468(17) 0.015(6) Uiso 1 1 d . . . H13 H 1.416(4) 0.931(3) 1.110(2) 0.031(7) Uiso 1 1 d . . . H10 H 0.948(4) 0.434(3) 0.831(2) 0.039(8) Uiso 1 1 d . . . H16 H 1.164(3) 0.132(2) 0.9376(18) 0.017(6) Uiso 1 1 d . . . H11 H 0.933(3) 0.653(2) 0.8809(17) 0.016(6) Uiso 1 1 d . . . H4 H 0.290(3) 0.808(2) 0.7616(18) 0.022(6) Uiso 1 1 d . . . H3 H -0.019(3) 0.668(2) 0.6604(18) 0.021(6) Uiso 1 1 d . . . H1 H 0.146(4) 0.359(3) 0.6241(19) 0.026(6) Uiso 1 1 d . . . H5 H 0.576(4) 0.344(3) 0.685(2) 0.043(8) Uiso 1 1 d . . . H2 H -0.087(4) 0.446(2) 0.589(2) 0.034(7) Uiso 1 1 d . . . S1 S 1.03328(7) 0.04538(5) 0.66630(4) 0.01308(12) Uani 1 1 d . . . N2 N 1.0987(2) 0.13790(15) 0.78700(12) 0.0135(3) Uani 1 1 d . . . O7 O 0.7464(2) 0.29030(13) 0.73907(11) 0.0200(3) Uani 1 1 d . . . O8 O 1.3049(2) 0.38754(13) 0.92081(11) 0.0181(3) Uani 1 1 d . . . O5 O 1.1027(2) -0.05969(13) 0.67248(11) 0.0180(3) Uani 1 1 d . . . O6 O 1.0839(2) 0.13031(13) 0.60345(11) 0.0181(3) Uani 1 1 d . . . N4 N 1.0600(2) 0.45886(16) 0.87807(13) 0.0158(3) Uani 1 1 d . . . N3 N 1.3280(2) 0.62692(16) 1.00750(13) 0.0154(3) Uani 1 1 d . . . C16 C 0.8256(3) 0.20544(19) 0.73574(15) 0.0145(4) Uani 1 1 d . . . C9 C 0.7090(3) 0.06731(19) 0.66760(14) 0.0140(4) Uani 1 1 d . . . C15 C 1.0140(3) 0.23664(19) 0.79441(15) 0.0142(4) Uani 1 1 d . . . C18 C 1.1516(3) 0.58703(19) 0.93900(14) 0.0141(4) Uani 1 1 d . . . C13 C 0.7890(3) -0.01858(19) 0.62996(15) 0.0134(4) Uani 1 1 d . . . C8 C 0.6816(3) -0.1473(2) 0.56774(15) 0.0156(4) Uani 1 1 d . . . C19 C 1.0641(3) 0.6797(2) 0.93252(15) 0.0167(4) Uani 1 1 d . . . C17 C 1.1400(3) 0.36324(19) 0.86805(15) 0.0146(4) Uani 1 1 d . . . C14 C 1.1017(3) 0.0671(2) 0.86875(16) 0.0188(4) Uani 1 1 d . . . C21 C 1.3452(3) 0.8448(2) 1.06616(16) 0.0200(4) Uani 1 1 d . . . C10 C 0.5144(3) 0.0202(2) 0.63849(15) 0.0162(4) Uani 1 1 d . . . C22 C 1.4251(3) 0.7516(2) 1.07148(16) 0.0193(4) Uani 1 1 d . . . C11 C 0.4056(3) -0.1087(2) 0.57626(16) 0.0179(4) Uani 1 1 d . . . C20 C 1.1631(3) 0.8074(2) 0.99525(16) 0.0184(4) Uani 1 1 d . . . C12 C 0.4886(3) -0.1922(2) 0.54122(16) 0.0177(4) Uani 1 1 d . . . O1 O 0.6239(2) 0.50993(14) 0.82576(11) 0.0204(3) Uani 1 1 d . . . O3 O 0.7120(2) 0.74619(15) 0.77082(13) 0.0270(4) Uani 1 1 d . . . O2 O 0.4838(2) 0.37361(15) 0.66135(12) 0.0236(3) Uani 1 1 d . . . N1 N 0.5916(3) 0.75985(17) 0.80497(14) 0.0215(4) Uani 1 1 d . . . O4 O 0.6210(3) 0.84918(15) 0.88166(13) 0.0355(4) Uani 1 1 d . . . C7 C 0.5055(3) 0.47237(19) 0.73863(15) 0.0153(4) Uani 1 1 d . . . C1 C 0.3591(3) 0.53153(19) 0.70823(15) 0.0148(4) Uani 1 1 d . . . C2 C 0.2581(3) 0.7181(2) 0.73286(17) 0.0209(4) Uani 1 1 d . . . C6 C 0.1746(3) 0.4503(2) 0.64859(17) 0.0198(4) Uani 1 1 d . . . C5 C 0.3969(3) 0.66624(19) 0.74899(15) 0.0162(4) Uani 1 1 d . . . C3 C 0.0747(3) 0.6350(2) 0.67351(18) 0.0232(5) Uani 1 1 d . . . C4 C 0.0336(3) 0.5017(2) 0.63138(18) 0.0233(5) 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 0.0114(2) 0.0113(2) 0.0166(2) 0.00141(17) 0.00524(18) 0.00535(18) N2 0.0142(8) 0.0111(8) 0.0145(7) 0.0015(6) 0.0031(6) 0.0068(7) O7 0.0155(7) 0.0151(7) 0.0270(8) 0.0003(6) 0.0037(6) 0.0090(6) O8 0.0153(7) 0.0151(7) 0.0203(7) 0.0003(6) 0.0023(6) 0.0069(6) O5 0.0149(7) 0.0146(7) 0.0241(7) 0.0021(6) 0.0053(6) 0.0086(6) O6 0.0192(8) 0.0148(7) 0.0214(7) 0.0044(6) 0.0103(6) 0.0052(6) N4 0.0138(9) 0.0132(8) 0.0168(8) -0.0003(7) 0.0019(7) 0.0062(7) N3 0.0169(9) 0.0128(8) 0.0157(8) 0.0019(7) 0.0041(7) 0.0074(7) C16 0.0170(10) 0.0136(9) 0.0154(9) 0.0035(7) 0.0075(8) 0.0078(8) C9 0.0151(10) 0.0145(9) 0.0133(9) 0.0044(7) 0.0050(8) 0.0064(8) C15 0.0159(10) 0.0123(9) 0.0160(9) 0.0017(7) 0.0057(8) 0.0085(8) C18 0.0159(10) 0.0143(9) 0.0130(8) 0.0036(7) 0.0062(8) 0.0062(8) C13 0.0118(9) 0.0137(9) 0.0152(9) 0.0043(7) 0.0047(7) 0.0055(8) C8 0.0173(10) 0.0147(10) 0.0155(9) 0.0018(7) 0.0061(8) 0.0081(8) C19 0.0180(10) 0.0188(10) 0.0164(9) 0.0056(8) 0.0075(8) 0.0096(9) C17 0.0171(10) 0.0135(9) 0.0154(9) 0.0032(7) 0.0074(8) 0.0075(8) C14 0.0211(11) 0.0187(11) 0.0183(10) 0.0062(8) 0.0063(9) 0.0096(9) C21 0.0227(11) 0.0139(10) 0.0210(10) 0.0004(8) 0.0078(9) 0.0063(9) C10 0.0150(10) 0.0183(10) 0.0182(9) 0.0046(8) 0.0071(8) 0.0094(9) C22 0.0176(11) 0.0171(10) 0.0196(10) 0.0014(8) 0.0039(8) 0.0062(9) C11 0.0130(10) 0.0226(11) 0.0177(9) 0.0056(8) 0.0059(8) 0.0060(9) C20 0.0249(11) 0.0170(10) 0.0216(10) 0.0078(8) 0.0127(9) 0.0135(9) C12 0.0155(10) 0.0160(10) 0.0168(9) 0.0012(8) 0.0043(8) 0.0027(8) O1 0.0211(8) 0.0197(7) 0.0196(7) 0.0042(6) 0.0035(6) 0.0106(6) O3 0.0198(8) 0.0233(8) 0.0368(9) 0.0122(7) 0.0087(7) 0.0059(7) O2 0.0218(8) 0.0212(8) 0.0244(8) -0.0024(6) 0.0017(6) 0.0145(7) N1 0.0239(10) 0.0126(8) 0.0218(9) 0.0048(7) 0.0001(8) 0.0057(8) O4 0.0429(11) 0.0200(8) 0.0272(8) -0.0064(7) -0.0045(8) 0.0128(8) C7 0.0156(10) 0.0134(9) 0.0191(9) 0.0064(8) 0.0073(8) 0.0063(8) C1 0.0163(10) 0.0156(10) 0.0152(9) 0.0053(8) 0.0069(8) 0.0078(8) C2 0.0293(12) 0.0184(11) 0.0220(10) 0.0080(9) 0.0120(9) 0.0144(10) C6 0.0211(11) 0.0152(10) 0.0237(10) 0.0064(8) 0.0080(9) 0.0070(9) C5 0.0188(10) 0.0146(9) 0.0147(9) 0.0036(7) 0.0051(8) 0.0067(8) C3 0.0228(11) 0.0269(12) 0.0296(11) 0.0139(10) 0.0120(9) 0.0166(10) C4 0.0155(11) 0.0241(11) 0.0302(11) 0.0111(10) 0.0066(9) 0.0067(9) _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 O6 1.4313(14) . ? S1 O5 1.4378(14) . ? S1 N2 1.6461(16) . ? S1 C13 1.757(2) . ? N2 C15 1.456(2) . ? N2 C14 1.478(3) . ? O7 C16 1.285(2) . ? O8 C17 1.236(2) . ? N4 C18 1.368(3) . ? N4 C17 1.402(2) . ? N4 H10 0.88(3) . ? N3 C18 1.347(3) . ? N3 C22 1.355(3) . ? N3 H15 0.88(2) . ? C16 C15 1.400(3) . ? C16 C9 1.498(3) . ? C9 C10 1.399(3) . ? C9 C13 1.408(3) . ? C15 C17 1.447(3) . ? C18 C19 1.409(3) . ? C13 C8 1.390(3) . ? C8 C12 1.392(3) . ? C8 H6 0.92(2) . ? C19 C20 1.376(3) . ? C19 H11 1.01(2) . ? C14 H17 0.99(2) . ? C14 H18 0.98(3) . ? C14 H16 0.98(2) . ? C21 C22 1.371(3) . ? C21 C20 1.397(3) . ? C21 H13 0.94(3) . ? C10 C11 1.393(3) . ? C10 H9 0.88(2) . ? C22 H14 0.94(2) . ? C11 C12 1.393(3) . ? C11 H8 0.94(2) . ? C20 H12 0.94(2) . ? C12 H7 0.99(2) . ? O1 C7 1.212(2) . ? O3 N1 1.229(2) . ? O2 C7 1.324(2) . ? O2 H5 0.90(3) . ? N1 O4 1.233(2) . ? N1 C5 1.476(3) . ? C7 C1 1.505(3) . ? C1 C6 1.390(3) . ? C1 C5 1.405(3) . ? C2 C5 1.383(3) . ? C2 C3 1.388(3) . ? C2 H4 0.93(2) . ? C6 C4 1.396(3) . ? C6 H1 0.94(2) . ? C3 C4 1.388(3) . ? C3 H3 0.92(2) . ? C4 H2 0.93(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 O6 S1 O5 119.28(9) . . ? O6 S1 N2 108.07(8) . . ? O5 S1 N2 107.42(8) . . ? O6 S1 C13 109.41(9) . . ? O5 S1 C13 109.66(9) . . ? N2 S1 C13 101.49(9) . . ? C15 N2 C14 114.62(15) . . ? C15 N2 S1 113.44(12) . . ? C14 N2 S1 115.88(13) . . ? C18 N4 C17 125.91(18) . . ? C18 N4 H10 120.6(18) . . ? C17 N4 H10 112.4(18) . . ? C18 N3 C22 123.31(18) . . ? C18 N3 H15 117.8(16) . . ? C22 N3 H15 118.9(16) . . ? O7 C16 C15 122.65(18) . . ? O7 C16 C9 118.09(17) . . ? C15 C16 C9 119.26(17) . . ? C10 C9 C13 117.84(18) . . ? C10 C9 C16 120.22(17) . . ? C13 C9 C16 121.94(18) . . ? C16 C15 C17 125.28(17) . . ? C16 C15 N2 120.80(17) . . ? C17 C15 N2 113.90(16) . . ? N3 C18 N4 120.36(17) . . ? N3 C18 C19 118.51(18) . . ? N4 C18 C19 121.13(18) . . ? C8 C13 C9 122.14(18) . . ? C8 C13 S1 121.45(15) . . ? C9 C13 S1 116.42(14) . . ? C13 C8 C12 118.78(18) . . ? C13 C8 H6 119.0(14) . . ? C12 C8 H6 122.2(14) . . ? C20 C19 C18 118.66(19) . . ? C20 C19 H11 121.4(12) . . ? C18 C19 H11 119.9(12) . . ? O8 C17 N4 121.06(18) . . ? O8 C17 C15 124.11(17) . . ? N4 C17 C15 114.81(17) . . ? N2 C14 H17 110.8(14) . . ? N2 C14 H18 110.3(14) . . ? H17 C14 H18 110.3(19) . . ? N2 C14 H16 108.6(13) . . ? H17 C14 H16 104.7(19) . . ? H18 C14 H16 112.0(19) . . ? C22 C21 C20 118.6(2) . . ? C22 C21 H13 118.4(16) . . ? C20 C21 H13 123.0(16) . . ? C11 C10 C9 120.45(18) . . ? C11 C10 H9 119.3(15) . . ? C9 C10 H9 120.2(15) . . ? N3 C22 C21 119.7(2) . . ? N3 C22 H14 115.8(14) . . ? C21 C22 H14 124.5(14) . . ? C10 C11 C12 120.54(19) . . ? C10 C11 H8 117.2(14) . . ? C12 C11 H8 122.2(14) . . ? C19 C20 C21 121.19(19) . . ? C19 C20 H12 119.6(15) . . ? C21 C20 H12 119.2(15) . . ? C8 C12 C11 120.24(19) . . ? C8 C12 H7 119.3(14) . . ? C11 C12 H7 120.4(14) . . ? C7 O2 H5 107.0(18) . . ? O3 N1 O4 124.5(2) . . ? O3 N1 C5 118.33(17) . . ? O4 N1 C5 117.17(19) . . ? O1 C7 O2 125.19(18) . . ? O1 C7 C1 122.48(17) . . ? O2 C7 C1 112.29(17) . . ? C6 C1 C5 117.42(18) . . ? C6 C1 C7 120.12(17) . . ? C5 C1 C7 121.98(18) . . ? C5 C2 C3 119.2(2) . . ? C5 C2 H4 119.1(16) . . ? C3 C2 H4 121.7(15) . . ? C1 C6 C4 120.6(2) . . ? C1 C6 H1 118.6(16) . . ? C4 C6 H1 120.7(16) . . ? C2 C5 C1 122.4(2) . . ? C2 C5 N1 117.36(18) . . ? C1 C5 N1 120.11(17) . . ? C2 C3 C4 119.6(2) . . ? C2 C3 H3 120.3(15) . . ? C4 C3 H3 120.0(15) . . ? C3 C4 C6 120.7(2) . . ? C3 C4 H2 120.7(16) . . ? C6 C4 H2 118.5(16) . . ? _diffrn_measured_fraction_theta_max 0.959 _diffrn_reflns_theta_full 29.51 _diffrn_measured_fraction_theta_full 0.959 _refine_diff_density_max 0.560 _refine_diff_density_min -0.416 _refine_diff_density_rms 0.075 # Attachment 'PXZ 3FBA.cif' data_shelxl_PXZ_3FBA _database_code_depnum_ccdc_archive 'CCDC 890560' #TrackingRef 'PXZ 3FBA.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H13 N3 O4 S, C7 H5 F O2' _chemical_formula_sum 'C22 H18 F N3 O6 S' _chemical_formula_weight 471.45 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' F F 0.0171 0.0103 '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 P21/c 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 10.415(11) _cell_length_b 21.17(2) _cell_length_c 9.557(10) _cell_angle_alpha 90.00 _cell_angle_beta 100.053(13) _cell_angle_gamma 90.00 _cell_volume 2075(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3872 _cell_measurement_theta_min 1.9 _cell_measurement_theta_max 26.7 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.509 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 976 _exptl_absorpt_coefficient_mu 0.212 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7083 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'ABSCOR, Rigaku 1995' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.68890 _diffrn_radiation_type synchrotron _diffrn_radiation_source synchrotron _diffrn_radiation_monochromator 'silicon 111' _diffrn_measurement_device_type 'Rigaku Saturn CCD' _diffrn_measurement_method 'profile data from \w-scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18646 _diffrn_reflns_av_R_equivalents 0.0934 _diffrn_reflns_av_sigmaI/netI 0.0841 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 26.67 _reflns_number_total 4796 _reflns_number_gt 2932 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010)' _computing_cell_refinement 'CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010)' _computing_data_reduction 'CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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. Hydrogen refinement details: Hydrogen atoms not involved in hydrogen bonds were placed on calculated positions and refined as riding on the atoms to which they were bonded. The H-atoms involved in hydrogen bonds were then identified using the Fourier difference synthesis and allowed to freely refine but with the size of the thermal parameter constrained to be proportional to the atom to which it was bonded (H5, H6 and H7). Problem: PLAT355_ALERT_3_A Long O-H Bond (0.82A) O6 - H7...1.18 Ang. Response:This hydrogen atom has been identified in a Fourier difference map and the position and isotropic thermal parameter has been freely refined. The elongated bond length may be a consequence of the fact that it is involved in a relatively strong hydrogen bond and that the diffraction data were weak and of poor resolution due to small needle shaped crystals. Problem: DIFMX01_ALERT_2_C The maximum difference density is > 0.1*ZMAX*0.75 _refine_diff_density_max given = 1.224 Test value = 1.200 DIFMX02_ALERT_1_C The maximum difference density is > 0.1*ZMAX*0.75 The relevant atom site should be identified. RFACR01_ALERT_3_C The value of the weighted R factor is > 0.25 Weighted R factor given 0.294 PLAT148_ALERT_3_C su on the a - Axis is (Too) Large .....0.011 Ang. PLAT148_ALERT_3_C su on the c - Axis is (Too) Large .....0.010 Ang. PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds ............0.0067 Ang Response: Small, poorly diffracting, needle shaped crystals resulted in weak data with poor resolution. Data collection was not possible using a lab source diffractometer and the data presented are the best posssible from a synchrotron source. Maxima on Fourier map do not correspond to possible atom positions and are a result of the poor quality of the data. The maximum peak of 1.22e/A ^3^ lies between the carboxylic hydroxyl oxygen and the aromatic H of the ring - 1.356A from the O and 1.675A from the H atom. ; _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^)+(0.1696P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4796 _refine_ls_number_parameters 308 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1437 _refine_ls_R_factor_gt 0.0952 _refine_ls_wR_factor_ref 0.2938 _refine_ls_wR_factor_gt 0.2475 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _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 0.18344(11) 0.66124(5) 0.72076(12) 0.0339(3) Uani 1 1 d . . . O1 O 0.2803(3) 0.50183(13) 0.9878(3) 0.0375(8) Uani 1 1 d . . . O2 O 0.3064(3) 0.68577(13) 0.7894(3) 0.0378(8) Uani 1 1 d . . . N3 N 0.5673(4) 0.42248(15) 0.6668(4) 0.0315(8) Uani 1 1 d . . . H6 H 0.546(5) 0.455(2) 0.608(5) 0.047 Uiso 1 1 d . . . O3 O 0.1069(3) 0.69776(14) 0.6107(3) 0.0409(8) Uani 1 1 d . . . O4 O 0.4062(3) 0.51608(13) 0.5994(3) 0.0356(7) Uani 1 1 d . . . N2 N 0.4238(4) 0.46199(16) 0.8090(4) 0.0352(9) Uani 1 1 d . . . H5 H 0.400(5) 0.459(2) 0.893(5) 0.042 Uiso 1 1 d . . . N1 N 0.2091(4) 0.59171(15) 0.6565(4) 0.0312(8) Uani 1 1 d . . . O6 O 0.7362(4) 0.54882(15) 0.7707(4) 0.0490(9) Uani 1 1 d . . . H7 H 0.738(6) 0.527(3) 0.885(7) 0.074 Uiso 1 1 d . . . C8 C 0.2698(4) 0.54730(17) 0.7621(4) 0.0302(9) Uani 1 1 d . . . C7 C 0.2293(4) 0.54227(18) 0.8932(5) 0.0317(9) Uani 1 1 d . . . C14 C 0.6622(5) 0.38215(18) 0.6382(5) 0.0353(10) Uani 1 1 d . . . H14 H 0.6944 0.3859 0.5537 0.042 Uiso 1 1 calc R . . C10 C 0.5168(4) 0.41954(18) 0.7868(5) 0.0306(9) Uani 1 1 d . . . O5 O 0.5958(4) 0.61482(17) 0.8509(4) 0.0532(10) Uani 1 1 d . . . C9 C 0.3704(4) 0.50926(18) 0.7161(5) 0.0323(10) Uani 1 1 d . . . C12 C 0.6585(4) 0.33180(18) 0.8592(5) 0.0336(10) Uani 1 1 d . . . H12 H 0.6898 0.3006 0.9249 0.040 Uiso 1 1 calc R . . C5 C 0.1262(4) 0.58554(19) 0.9273(5) 0.0327(10) Uani 1 1 d . . . C11 C 0.5633(5) 0.37257(18) 0.8865(5) 0.0350(10) Uani 1 1 d . . . H11 H 0.5300 0.3691 0.9703 0.042 Uiso 1 1 calc R . . C6 C 0.0605(5) 0.5709(2) 1.0390(5) 0.0387(11) Uani 1 1 d . . . H4 H 0.0826 0.5345 1.0924 0.046 Uiso 1 1 calc R . . F1 F 0.8479(4) 0.65288(18) 0.3433(4) 0.0720(11) Uani 1 1 d . . . C4 C 0.0908(4) 0.64190(19) 0.8529(5) 0.0338(10) Uani 1 1 d . . . C3 C -0.0048(5) 0.6818(2) 0.8850(6) 0.0423(11) Uani 1 1 d . . . H3 H -0.0256 0.7190 0.8343 0.051 Uiso 1 1 calc R . . C21 C 0.6639(5) 0.6366(2) 0.6278(5) 0.0390(11) Uani 1 1 d . . . C20 C 0.7548(5) 0.6252(2) 0.5417(5) 0.0428(12) Uani 1 1 d . . . H15 H 0.8149 0.5925 0.5616 0.051 Uiso 1 1 calc R . . C2 C -0.0689(5) 0.6650(2) 0.9947(6) 0.0439(12) Uani 1 1 d . . . H2 H -0.1341 0.6912 1.0171 0.053 Uiso 1 1 calc R . . C13 C 0.7086(5) 0.33702(18) 0.7329(5) 0.0338(10) Uani 1 1 d . . . H13 H 0.7734 0.3096 0.7147 0.041 Uiso 1 1 calc R . . C18 C 0.6677(5) 0.7114(2) 0.3898(5) 0.0449(12) Uani 1 1 d . . . H18 H 0.6705 0.7364 0.3104 0.054 Uiso 1 1 calc R . . C15 C 0.1025(5) 0.5647(2) 0.5513(5) 0.0397(11) Uani 1 1 d . . . H8 H 0.1364 0.5317 0.4993 0.059 Uiso 1 1 calc R . . H9 H 0.0651 0.5972 0.4866 0.059 Uiso 1 1 calc R . . H10 H 0.0367 0.5478 0.5995 0.059 Uiso 1 1 calc R . . C22 C 0.6601(5) 0.5986(2) 0.7611(5) 0.0426(11) Uani 1 1 d . . . C17 C 0.5756(5) 0.7215(2) 0.4759(5) 0.0448(12) Uani 1 1 d . . . H17 H 0.5144 0.7535 0.4534 0.054 Uiso 1 1 calc R . . C19 C 0.7536(5) 0.6636(2) 0.4260(6) 0.0475(13) Uani 1 1 d . . . C1 C -0.0380(5) 0.6104(2) 1.0713(6) 0.0449(12) Uani 1 1 d . . . H1 H -0.0825 0.5998 1.1443 0.054 Uiso 1 1 calc R . . C16 C 0.5733(5) 0.6848(2) 0.5943(5) 0.0409(11) Uani 1 1 d . . . H16 H 0.5113 0.6922 0.6516 0.049 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 0.0415(7) 0.0185(5) 0.0417(6) 0.0017(4) 0.0068(5) 0.0034(4) O1 0.047(2) 0.0230(14) 0.0431(17) 0.0068(13) 0.0094(15) 0.0051(13) O2 0.049(2) 0.0219(14) 0.0432(17) 0.0012(12) 0.0086(15) -0.0057(13) N3 0.037(2) 0.0184(16) 0.0384(19) 0.0026(14) 0.0038(16) 0.0029(14) O3 0.051(2) 0.0266(15) 0.0430(17) 0.0055(13) 0.0024(15) 0.0121(14) O4 0.044(2) 0.0229(14) 0.0397(17) 0.0044(12) 0.0071(14) 0.0062(13) N2 0.046(2) 0.0222(16) 0.0377(19) 0.0053(15) 0.0073(17) 0.0048(16) N1 0.040(2) 0.0199(15) 0.0322(18) 0.0007(13) 0.0014(15) 0.0057(15) O6 0.063(3) 0.0334(17) 0.049(2) -0.0002(15) 0.0057(18) 0.0040(17) C8 0.037(3) 0.0166(17) 0.037(2) 0.0029(15) 0.0044(18) 0.0016(16) C7 0.035(2) 0.0185(17) 0.043(2) 0.0020(16) 0.0088(19) -0.0019(17) C14 0.043(3) 0.0212(19) 0.042(2) -0.0035(17) 0.008(2) 0.0024(18) C10 0.031(2) 0.0190(18) 0.041(2) 0.0027(16) 0.0043(18) 0.0019(16) O5 0.063(3) 0.049(2) 0.050(2) 0.0044(17) 0.0172(19) 0.0051(18) C9 0.035(3) 0.0204(19) 0.039(2) 0.0002(16) -0.0017(19) -0.0020(17) C12 0.040(3) 0.0201(18) 0.038(2) 0.0010(16) -0.0013(19) 0.0015(17) C5 0.037(3) 0.0222(19) 0.039(2) -0.0050(17) 0.0088(19) -0.0010(17) C11 0.043(3) 0.0214(19) 0.042(2) 0.0034(17) 0.010(2) 0.0003(18) C6 0.044(3) 0.028(2) 0.044(2) -0.0014(19) 0.007(2) -0.0018(19) F1 0.081(3) 0.089(3) 0.055(2) 0.0061(18) 0.0361(18) 0.014(2) C4 0.036(3) 0.0244(19) 0.039(2) -0.0043(17) 0.0026(19) -0.0026(18) C3 0.043(3) 0.028(2) 0.056(3) -0.007(2) 0.008(2) 0.006(2) C21 0.045(3) 0.032(2) 0.039(2) 0.0023(19) 0.004(2) -0.008(2) C20 0.043(3) 0.030(2) 0.054(3) -0.001(2) 0.007(2) 0.009(2) C2 0.042(3) 0.035(2) 0.057(3) -0.005(2) 0.016(2) 0.001(2) C13 0.041(3) 0.0188(18) 0.041(2) -0.0010(17) 0.0055(19) 0.0049(17) C18 0.058(3) 0.035(2) 0.038(2) 0.003(2) 0.000(2) -0.009(2) C15 0.041(3) 0.031(2) 0.046(3) -0.005(2) 0.003(2) 0.002(2) C22 0.048(3) 0.039(2) 0.041(2) -0.003(2) 0.007(2) -0.003(2) C17 0.046(3) 0.024(2) 0.058(3) -0.006(2) -0.006(2) 0.006(2) C19 0.051(3) 0.049(3) 0.047(3) -0.007(2) 0.020(2) -0.002(2) C1 0.047(3) 0.034(2) 0.057(3) -0.008(2) 0.020(2) -0.002(2) C16 0.038(3) 0.037(2) 0.048(3) -0.006(2) 0.007(2) -0.004(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O3 1.431(3) . ? S1 O2 1.431(4) . ? S1 N1 1.635(4) . ? S1 C4 1.766(5) . ? O1 C7 1.290(5) . ? N3 C10 1.344(6) . ? N3 C14 1.369(6) . ? N3 H6 0.89(5) . ? O4 C9 1.245(5) . ? N2 C10 1.365(5) . ? N2 C9 1.388(5) . ? N2 H5 0.88(5) . ? N1 C8 1.442(5) . ? N1 C15 1.477(6) . ? O6 C22 1.312(6) . ? O6 H7 1.19(6) . ? C8 C7 1.393(6) . ? C8 C9 1.449(6) . ? C7 C5 1.491(6) . ? C14 C13 1.347(6) . ? C14 H14 0.9300 . ? C10 C11 1.404(6) . ? O5 C22 1.227(6) . ? C12 C11 1.373(6) . ? C12 C13 1.401(6) . ? C12 H12 0.9300 . ? C5 C6 1.399(6) . ? C5 C4 1.405(6) . ? C11 H11 0.9300 . ? C6 C1 1.400(7) . ? C6 H4 0.9300 . ? F1 C19 1.382(6) . ? C4 C3 1.380(6) . ? C3 C2 1.384(7) . ? C3 H3 0.9300 . ? C21 C20 1.380(7) . ? C21 C16 1.388(7) . ? C21 C22 1.514(7) . ? C20 C19 1.371(7) . ? C20 H15 0.9300 . ? C2 C1 1.376(7) . ? C2 H2 0.9300 . ? C13 H13 0.9300 . ? C18 C19 1.356(7) . ? C18 C17 1.385(7) . ? C18 H18 0.9300 . ? C15 H8 0.9600 . ? C15 H9 0.9600 . ? C15 H10 0.9600 . ? C17 C16 1.377(7) . ? C17 H17 0.9300 . ? C1 H1 0.9300 . ? C16 H16 0.9300 . ? 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 O3 S1 O2 118.7(2) . . ? O3 S1 N1 108.46(19) . . ? O2 S1 N1 107.9(2) . . ? O3 S1 C4 110.3(2) . . ? O2 S1 C4 108.3(2) . . ? N1 S1 C4 101.87(19) . . ? C10 N3 C14 123.0(4) . . ? C10 N3 H6 119(3) . . ? C14 N3 H6 117(3) . . ? C10 N2 C9 126.3(4) . . ? C10 N2 H5 114(3) . . ? C9 N2 H5 120(3) . . ? C8 N1 C15 114.2(3) . . ? C8 N1 S1 113.8(3) . . ? C15 N1 S1 116.8(3) . . ? C22 O6 H7 107(3) . . ? C7 C8 N1 121.0(4) . . ? C7 C8 C9 125.3(4) . . ? N1 C8 C9 113.6(4) . . ? O1 C7 C8 121.9(4) . . ? O1 C7 C5 118.6(4) . . ? C8 C7 C5 119.5(4) . . ? C13 C14 N3 119.7(4) . . ? C13 C14 H14 120.2 . . ? N3 C14 H14 120.2 . . ? N3 C10 N2 119.8(4) . . ? N3 C10 C11 118.2(4) . . ? N2 C10 C11 122.1(4) . . ? O4 C9 N2 120.5(4) . . ? O4 C9 C8 123.6(4) . . ? N2 C9 C8 115.9(4) . . ? C11 C12 C13 120.3(4) . . ? C11 C12 H12 119.9 . . ? C13 C12 H12 119.9 . . ? C6 C5 C4 117.0(4) . . ? C6 C5 C7 119.8(4) . . ? C4 C5 C7 123.1(4) . . ? C12 C11 C10 119.4(4) . . ? C12 C11 H11 120.3 . . ? C10 C11 H11 120.3 . . ? C5 C6 C1 120.7(4) . . ? C5 C6 H4 119.7 . . ? C1 C6 H4 119.7 . . ? C3 C4 C5 122.9(4) . . ? C3 C4 S1 121.5(4) . . ? C5 C4 S1 115.5(3) . . ? C4 C3 C2 118.3(5) . . ? C4 C3 H3 120.9 . . ? C2 C3 H3 120.9 . . ? C20 C21 C16 120.1(4) . . ? C20 C21 C22 122.0(4) . . ? C16 C21 C22 117.9(4) . . ? C19 C20 C21 117.8(4) . . ? C19 C20 H15 121.1 . . ? C21 C20 H15 121.1 . . ? C1 C2 C3 121.3(5) . . ? C1 C2 H2 119.3 . . ? C3 C2 H2 119.3 . . ? C14 C13 C12 119.4(4) . . ? C14 C13 H13 120.3 . . ? C12 C13 H13 120.3 . . ? C19 C18 C17 117.3(5) . . ? C19 C18 H18 121.4 . . ? C17 C18 H18 121.4 . . ? N1 C15 H8 109.5 . . ? N1 C15 H9 109.5 . . ? H8 C15 H9 109.5 . . ? N1 C15 H10 109.5 . . ? H8 C15 H10 109.5 . . ? H9 C15 H10 109.5 . . ? O5 C22 O6 125.0(5) . . ? O5 C22 C21 122.5(5) . . ? O6 C22 C21 112.4(4) . . ? C16 C17 C18 121.0(4) . . ? C16 C17 H17 119.5 . . ? C18 C17 H17 119.5 . . ? C18 C19 C20 124.2(5) . . ? C18 C19 F1 118.6(5) . . ? C20 C19 F1 117.2(5) . . ? C2 C1 C6 119.8(5) . . ? C2 C1 H1 120.1 . . ? C6 C1 H1 120.1 . . ? C17 C16 C21 119.7(5) . . ? C17 C16 H16 120.1 . . ? C21 C16 H16 120.1 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.224 _refine_diff_density_min -0.811 _refine_diff_density_rms 0.104 # Attachment 'PXZ 3HBA H2O.cif' data_shelxl_PXZ_3HBA_H2O _database_code_depnum_ccdc_archive 'CCDC 890561' #TrackingRef 'PXZ 3HBA H2O.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H13 N3 O4 S, C7 H6 O3, H2 O' _chemical_formula_sum 'C22 H21 N3 O8 S' _chemical_formula_weight 487.48 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.1121(11) _cell_length_b 9.9763(13) _cell_length_c 11.9501(16) _cell_angle_alpha 78.5115(45) _cell_angle_beta 86.2011(44) _cell_angle_gamma 88.3753(45) _cell_volume 1062.1(2) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 19534 _cell_measurement_theta_min 1 _cell_measurement_theta_max 49.07 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.524 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 508 _exptl_absorpt_coefficient_mu 0.210 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7269 _exptl_absorpt_correction_T_max 1.0 _exptl_absorpt_process_details 'SADABS(Blessing, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'Bruker Apex II CCD' _diffrn_measurement_method 'CCD; rotation images' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19534 _diffrn_reflns_av_R_equivalents 0.1149 _diffrn_reflns_av_sigmaI/netI 0.1126 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.74 _diffrn_reflns_theta_max 24.54 _reflns_number_total 3477 _reflns_number_gt 2050 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2 (2009)' _computing_cell_refinement 'Bruker APEX2 (2009)' _computing_data_reduction 'Bruker APEX2 (2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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. Hydrogen refinement details: Hydrogen atoms not involved in hydrogen bonds were placed on calculated positions and refined as riding on the atoms to which they were bonded. The H-atoms involved in hydrogen bonds were then identified using the Fourier difference synthesis. The positions of H21 and H22 (water hydrogen atoms) were allowed to freely refine but the size of the thermal parameter was constrained to be proportional to the atom to which it was bonded. THETM01_ALERT_3_C The value of sine(theta_max)/wavelength is less than 0.590 Calculated sin(theta_max)/wavelength = 0.5844 PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.979 PLAT230_ALERT_2_C Hirshfeld Test Diff for S1 -- O5 .. 6.6 su PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.6 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.2 PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds ............. 0.0046 Ang Response: Small, poorly diffracting, needle shaped crystals resulted in weak data with poor resolution. Data presented is the best of several attempts at data collection.' PLAT007_ALERT_5_G Note: Number of Unrefined D-H Atoms ............ 1 Response: Water hydrogen atoms located via Fourier map and thermal parameters refined as riding model with adp of 1.5 x adp of oxygen atom. ; _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^)+(0.0457P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3477 _refine_ls_number_parameters 337 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1032 _refine_ls_R_factor_gt 0.0471 _refine_ls_wR_factor_ref 0.1070 _refine_ls_wR_factor_gt 0.0923 _refine_ls_goodness_of_fit_ref 0.908 _refine_ls_restrained_S_all 0.908 _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 O8 O 1.5071(3) 0.4570(3) 0.6618(2) 0.0302(7) Uani 1 1 d . . . H22 H 1.545(4) 0.532(4) 0.633(3) 0.045 Uiso 1 1 d . . . H21 H 1.556(4) 0.397(4) 0.651(3) 0.045 Uiso 1 1 d . . . H13 H 0.161(3) 0.410(3) 0.203(2) 0.021(9) Uiso 1 1 d . . . H14 H 0.049(3) 0.297(3) 0.273(3) 0.019(9) Uiso 1 1 d . . . H12 H 0.047(3) 0.323(3) 0.143(3) 0.028(9) Uiso 1 1 d . . . H5 H 1.351(4) 0.443(4) 0.580(3) 0.041(11) Uiso 1 1 d . . . H16 H 0.081(4) 0.015(3) 0.582(3) 0.040(10) Uiso 1 1 d . . . H7 H 0.715(4) 0.248(4) 0.401(3) 0.058(13) Uiso 1 1 d . . . S1 S 0.29030(9) 0.16350(10) 0.09503(7) 0.0218(3) Uani 1 1 d . . . O4 O 0.1237(2) 0.0652(2) 0.42672(17) 0.0212(6) Uani 1 1 d . . . O3 O 1.2800(2) 0.4248(2) 0.5359(2) 0.0255(6) Uani 1 1 d . . . N3 N 0.1496(3) 0.0175(3) 0.6487(2) 0.0180(7) Uani 1 1 d . . . N2 N 0.3330(3) 0.1067(3) 0.5093(2) 0.0193(7) Uani 1 1 d . . . H15 H 0.4228 0.1323 0.4951 0.023 Uiso 1 1 calc R . . O7 O 0.5458(2) 0.2240(2) 0.36854(18) 0.0229(6) Uani 1 1 d . . . O1 O 0.6583(2) 0.2381(2) 0.59095(18) 0.0259(6) Uani 1 1 d . . . O5 O 0.3301(2) 0.0213(2) 0.11604(18) 0.0231(6) Uani 1 1 d . . . O6 O 0.1932(2) 0.2142(2) 0.00625(18) 0.0264(6) Uani 1 1 d . . . O2 O 0.8045(2) 0.2649(2) 0.43017(19) 0.0223(6) Uani 1 1 d . . . C1 C 0.9089(3) 0.2941(3) 0.6006(3) 0.0182(8) Uani 1 1 d . . . C2 C 0.8960(3) 0.2744(3) 0.7198(3) 0.0216(8) Uani 1 1 d . . . H2 H 0.8097 0.2404 0.7601 0.026 Uiso 1 1 calc R . . C19 C 0.3803(3) 0.0666(3) 0.7100(3) 0.0189(8) Uani 1 1 d . . . H20 H 0.4762 0.0974 0.6936 0.023 Uiso 1 1 calc R . . C21 C 0.1824(3) -0.0217(3) 0.8462(3) 0.0211(8) Uani 1 1 d . . . H18 H 0.1461 -0.0498 0.9216 0.025 Uiso 1 1 calc R . . C8 C 0.6504(3) 0.3573(3) 0.1491(3) 0.0212(8) Uani 1 1 d . . . H8 H 0.6980 0.3743 0.2112 0.025 Uiso 1 1 calc R . . C11 C 0.5108(3) 0.3082(4) -0.0390(3) 0.0252(9) Uani 1 1 d . . . H11 H 0.4638 0.2917 -0.1015 0.030 Uiso 1 1 calc R . . C13 C 0.5201(3) 0.2842(3) 0.1674(3) 0.0187(8) Uani 1 1 d . . . C20 C 0.3270(3) 0.0233(3) 0.8216(3) 0.0196(8) Uani 1 1 d . . . H19 H 0.3877 0.0241 0.8811 0.024 Uiso 1 1 calc R . . C5 C 1.1547(3) 0.3755(3) 0.5996(3) 0.0206(8) Uani 1 1 d . . . N1 N 0.2174(3) 0.1998(3) 0.2139(2) 0.0184(7) Uani 1 1 d . . . C17 C 0.2485(3) 0.1135(3) 0.4155(3) 0.0174(8) Uani 1 1 d . . . C15 C 0.3157(3) 0.1815(3) 0.3059(3) 0.0178(8) Uani 1 1 d . . . C3 C 1.0130(3) 0.3061(3) 0.7774(3) 0.0245(9) Uani 1 1 d . . . H3 H 1.0050 0.2933 0.8568 0.029 Uiso 1 1 calc R . . C14 C 0.4589(3) 0.2296(3) 0.2868(3) 0.0179(8) Uani 1 1 d . . . C10 C 0.6401(3) 0.3805(3) -0.0549(3) 0.0254(9) Uani 1 1 d . . . H10 H 0.6804 0.4130 -0.1285 0.030 Uiso 1 1 calc R . . C18 C 0.2879(3) 0.0636(3) 0.6215(3) 0.0164(8) Uani 1 1 d . . . C6 C 1.0384(3) 0.3443(3) 0.5410(3) 0.0189(8) Uani 1 1 d . . . H6 H 1.0470 0.3570 0.4616 0.023 Uiso 1 1 calc R . . C22 C 0.0955(3) -0.0238(3) 0.7587(3) 0.0205(8) Uani 1 1 d . . . H17 H -0.0009 -0.0534 0.7739 0.025 Uiso 1 1 calc R . . C7 C 0.7803(4) 0.2638(3) 0.5411(3) 0.0200(8) Uani 1 1 d . . . C4 C 1.1425(3) 0.3568(3) 0.7179(3) 0.0222(9) Uani 1 1 d . . . H4 H 1.2205 0.3781 0.7572 0.027 Uiso 1 1 calc R . . C9 C 0.7099(3) 0.4049(3) 0.0387(3) 0.0247(9) Uani 1 1 d . . . H9 H 0.7971 0.4535 0.0274 0.030 Uiso 1 1 calc R . . C16 C 0.1119(4) 0.3167(4) 0.2079(3) 0.0234(9) Uani 1 1 d . . . C12 C 0.4519(3) 0.2605(3) 0.0712(3) 0.0183(8) 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 O8 0.0262(16) 0.0373(19) 0.0285(16) -0.0125(15) 0.0067(13) -0.0029(13) S1 0.0166(5) 0.0360(6) 0.0137(5) -0.0083(4) 0.0037(4) -0.0029(4) O4 0.0155(12) 0.0334(15) 0.0153(13) -0.0061(11) 0.0011(10) -0.0048(11) O3 0.0155(13) 0.0373(16) 0.0254(15) -0.0110(13) 0.0037(12) -0.0069(12) N3 0.0126(15) 0.0280(18) 0.0140(17) -0.0059(14) 0.0016(13) -0.0027(13) N2 0.0094(14) 0.0320(19) 0.0156(17) -0.0041(14) 0.0058(13) -0.0040(13) O7 0.0159(12) 0.0386(16) 0.0150(13) -0.0069(12) 0.0000(11) -0.0033(11) O1 0.0147(12) 0.0425(17) 0.0211(14) -0.0091(12) 0.0048(11) -0.0028(11) O5 0.0247(13) 0.0250(16) 0.0199(14) -0.0075(12) 0.0061(11) -0.0028(11) O6 0.0172(12) 0.0505(17) 0.0122(13) -0.0084(12) -0.0009(10) 0.0034(11) O2 0.0154(13) 0.0364(16) 0.0167(14) -0.0102(12) 0.0013(11) 0.0006(11) C1 0.0171(18) 0.023(2) 0.0155(19) -0.0063(16) 0.0013(15) 0.0020(15) C2 0.0149(18) 0.028(2) 0.022(2) -0.0075(18) 0.0040(16) 0.0005(16) C19 0.0142(17) 0.024(2) 0.018(2) -0.0060(17) 0.0015(16) 0.0018(15) C21 0.0224(19) 0.029(2) 0.0119(19) -0.0054(17) 0.0049(16) 0.0007(17) C8 0.0183(18) 0.026(2) 0.019(2) -0.0048(18) 0.0023(16) -0.0015(16) C11 0.0225(19) 0.037(2) 0.016(2) -0.0089(19) 0.0030(17) 0.0016(18) C13 0.0154(17) 0.024(2) 0.016(2) -0.0056(17) 0.0045(15) 0.0008(16) C20 0.0171(18) 0.029(2) 0.014(2) -0.0094(17) -0.0024(16) 0.0026(16) C5 0.0181(18) 0.024(2) 0.019(2) -0.0044(17) 0.0038(16) -0.0004(16) N1 0.0133(14) 0.0322(19) 0.0093(16) -0.0053(14) 0.0041(12) 0.0014(13) C17 0.0136(18) 0.025(2) 0.015(2) -0.0082(17) -0.0017(16) 0.0016(16) C15 0.0160(18) 0.026(2) 0.012(2) -0.0046(17) 0.0012(15) -0.0004(16) C3 0.0244(19) 0.033(2) 0.017(2) -0.0077(18) 0.0008(17) 0.0006(17) C14 0.0145(17) 0.024(2) 0.015(2) -0.0074(17) 0.0048(16) -0.0005(16) C10 0.024(2) 0.032(2) 0.018(2) -0.0041(18) 0.0095(17) -0.0007(17) C18 0.0140(17) 0.023(2) 0.012(2) -0.0058(17) 0.0046(15) 0.0026(15) C6 0.0196(18) 0.025(2) 0.0122(19) -0.0065(17) 0.0028(15) 0.0035(16) C22 0.0159(17) 0.029(2) 0.016(2) -0.0045(18) 0.0073(16) -0.0020(16) C7 0.0198(19) 0.023(2) 0.016(2) -0.0042(17) 0.0064(17) 0.0017(16) C4 0.0184(18) 0.030(2) 0.020(2) -0.0090(18) -0.0026(16) 0.0024(16) C9 0.0177(18) 0.031(2) 0.025(2) -0.0070(19) 0.0098(17) -0.0035(17) C16 0.019(2) 0.034(3) 0.016(2) -0.004(2) 0.0024(19) 0.0056(19) C12 0.0166(17) 0.023(2) 0.015(2) -0.0055(17) 0.0042(16) 0.0009(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 O8 H22 0.83(4) . ? O8 H21 0.77(4) . ? S1 O5 1.431(2) . ? S1 O6 1.431(2) . ? S1 N1 1.630(2) . ? S1 C12 1.761(3) . ? O4 C17 1.236(3) . ? O3 C5 1.376(4) . ? O3 H5 0.90(3) . ? N3 C18 1.350(4) . ? N3 C22 1.360(4) . ? N3 H16 1.05(3) . ? N2 C18 1.363(4) . ? N2 C17 1.391(4) . ? N2 H15 0.8600 . ? O7 C14 1.289(4) . ? O1 C7 1.235(4) . ? O2 C7 1.327(4) . ? O2 H7 0.94(4) . ? C1 C6 1.390(4) . ? C1 C2 1.397(4) . ? C1 C7 1.478(4) . ? C2 C3 1.383(4) . ? C2 H2 0.9300 . ? C19 C20 1.378(4) . ? C19 C18 1.400(4) . ? C19 H20 0.9300 . ? C21 C22 1.356(4) . ? C21 C20 1.398(4) . ? C21 H18 0.9300 . ? C8 C9 1.389(4) . ? C8 C13 1.393(4) . ? C8 H8 0.9300 . ? C11 C10 1.381(4) . ? C11 C12 1.386(4) . ? C11 H11 0.9300 . ? C13 C12 1.405(4) . ? C13 C14 1.499(4) . ? C20 H19 0.9300 . ? C5 C6 1.383(4) . ? C5 C4 1.386(4) . ? N1 C15 1.444(4) . ? N1 C16 1.484(4) . ? C17 C15 1.454(4) . ? C15 C14 1.392(4) . ? C3 C4 1.391(4) . ? C3 H3 0.9300 . ? C10 C9 1.388(4) . ? C10 H10 0.9300 . ? C6 H6 0.9300 . ? C22 H17 0.9300 . ? C4 H4 0.9300 . ? C9 H9 0.9300 . ? C16 H13 1.03(3) . ? C16 H14 0.92(3) . ? C16 H12 1.00(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 H22 O8 H21 112(4) . . ? O5 S1 O6 118.54(13) . . ? O5 S1 N1 108.17(14) . . ? O6 S1 N1 108.11(13) . . ? O5 S1 C12 108.81(14) . . ? O6 S1 C12 109.35(15) . . ? N1 S1 C12 102.70(14) . . ? C5 O3 H5 113(2) . . ? C18 N3 C22 122.6(3) . . ? C18 N3 H16 118.7(18) . . ? C22 N3 H16 118.7(18) . . ? C18 N2 C17 126.6(3) . . ? C18 N2 H15 116.7 . . ? C17 N2 H15 116.7 . . ? C7 O2 H7 108(2) . . ? C6 C1 C2 120.1(3) . . ? C6 C1 C7 121.8(3) . . ? C2 C1 C7 118.1(3) . . ? C3 C2 C1 119.3(3) . . ? C3 C2 H2 120.4 . . ? C1 C2 H2 120.4 . . ? C20 C19 C18 119.0(3) . . ? C20 C19 H20 120.5 . . ? C18 C19 H20 120.5 . . ? C22 C21 C20 119.2(3) . . ? C22 C21 H18 120.4 . . ? C20 C21 H18 120.4 . . ? C9 C8 C13 120.5(3) . . ? C9 C8 H8 119.8 . . ? C13 C8 H8 119.8 . . ? C10 C11 C12 119.3(3) . . ? C10 C11 H11 120.4 . . ? C12 C11 H11 120.4 . . ? C8 C13 C12 118.0(3) . . ? C8 C13 C14 120.2(3) . . ? C12 C13 C14 121.8(3) . . ? C19 C20 C21 120.5(3) . . ? C19 C20 H19 119.8 . . ? C21 C20 H19 119.8 . . ? O3 C5 C6 117.4(3) . . ? O3 C5 C4 122.4(3) . . ? C6 C5 C4 120.2(3) . . ? C15 N1 C16 115.9(3) . . ? C15 N1 S1 114.5(2) . . ? C16 N1 S1 118.8(2) . . ? O4 C17 N2 121.1(3) . . ? O4 C17 C15 123.1(3) . . ? N2 C17 C15 115.8(3) . . ? C14 C15 N1 120.9(3) . . ? C14 C15 C17 125.6(3) . . ? N1 C15 C17 113.5(3) . . ? C2 C3 C4 120.7(3) . . ? C2 C3 H3 119.7 . . ? C4 C3 H3 119.7 . . ? O7 C14 C15 122.4(3) . . ? O7 C14 C13 117.4(3) . . ? C15 C14 C13 120.2(3) . . ? C11 C10 C9 120.2(3) . . ? C11 C10 H10 119.9 . . ? C9 C10 H10 119.9 . . ? N3 C18 N2 119.3(3) . . ? N3 C18 C19 118.8(3) . . ? N2 C18 C19 122.0(3) . . ? C5 C6 C1 120.0(3) . . ? C5 C6 H6 120.0 . . ? C1 C6 H6 120.0 . . ? C21 C22 N3 120.0(3) . . ? C21 C22 H17 120.0 . . ? N3 C22 H17 120.0 . . ? O1 C7 O2 121.8(3) . . ? O1 C7 C1 122.5(3) . . ? O2 C7 C1 115.7(3) . . ? C5 C4 C3 119.7(3) . . ? C5 C4 H4 120.2 . . ? C3 C4 H4 120.2 . . ? C10 C9 C8 120.4(3) . . ? C10 C9 H9 119.8 . . ? C8 C9 H9 119.8 . . ? N1 C16 H13 114.0(16) . . ? N1 C16 H14 106.4(19) . . ? H13 C16 H14 110(2) . . ? N1 C16 H12 111.7(17) . . ? H13 C16 H12 109(2) . . ? H14 C16 H12 105(2) . . ? C11 C12 C13 121.6(3) . . ? C11 C12 S1 120.6(2) . . ? C13 C12 S1 117.8(2) . . ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 24.54 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.351 _refine_diff_density_min -0.456 _refine_diff_density_rms 0.068 # Attachment 'PXZ 3MBA ACN.cif' data_shelxl_PXZ_3MBA_ACN _database_code_depnum_ccdc_archive 'CCDC 890562' #TrackingRef 'PXZ 3MBA ACN.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C15 H13 N3 O4 S), C8 H8 O2, C2 H3 N' _chemical_formula_sum 'C40 H37 N7 O10 S2' _chemical_formula_weight 839.91 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.4985(2) _cell_length_b 9.8813(2) _cell_length_c 12.5408(3) _cell_angle_alpha 93.6020(10) _cell_angle_beta 104.0920(10) _cell_angle_gamma 112.1530(10) _cell_volume 931.91(4) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 19901 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.10 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.497 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 438 _exptl_absorpt_coefficient_mu 0.216 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.626 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'SADABS (Blessing, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 KappaCCD _diffrn_measurement_method 'CCD; rotation images' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19882 _diffrn_reflns_av_R_equivalents 0.1337 _diffrn_reflns_av_sigmaI/netI 0.0785 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.70 _diffrn_reflns_theta_max 27.15 _reflns_number_total 4108 _reflns_number_gt 2874 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo & Scalepack(Otwinowski,Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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. Disorder refinement details: Refined with 50:50 occupancy of the two positions for the 3-methylbenzoic acid and acetonitrile molecules across an inversion centre. Due to overlapping regions of electron density, the ADPs of similar atoms were constrained to be equal to ensure a well-behaved refinement. This allowed anisotropic refinement of all non-hydrogen atoms. H-atoms were identified using the Fourier difference synthesis for the non-disordered PX molecule and the remaining disordered H-atoms placed in calculated positions with the exception of the carboxylic H24 which was found using Fourier difference synthesis and allowed to freely refine at 50% occupancy. Problem: PLAT420_ALERT_2_B D-H Without Acceptor *O6 - *H25B ... ? PLAT420_ALERT_2_B D-H Without Acceptor *O6 - *H25C ... ? PLAT007_ALERT_5_G Note: Number of Unrefined D-H Atoms ............ 2 Response: Result of overlap of 50% occupied disordered molecules. H2B and H25C are methyl hydrogens on the acetonitrile molecule whilst O6 is from the overlapping 3-methylbenzoic acid molecule. Problem: PLAT432_ALERT_2_G Short Inter X...Y Contact O5 .. C20 .. 2.82 Ang. PLAT432_ALERT_2_G Short Inter X...Y Contact N4 .. C20 .. 2.01 Ang. Response: O5 .. C20 is an intramolecular distance. N4 .. C20 is again a result of the overlapping disordered molecules with each atom from a different residue. ; _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^)+(0.0625P)^2^+0.6583P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4108 _refine_ls_number_parameters 341 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0929 _refine_ls_R_factor_gt 0.0562 _refine_ls_wR_factor_ref 0.1493 _refine_ls_wR_factor_gt 0.1316 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.071 _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 C17 C 0.8146(10) 0.4544(9) 0.8813(5) 0.0242(6) Uani 0.50 1 d P . . H17 H 0.8066 0.4604 0.8066 0.029 Uiso 0.50 1 calc PR . . C18 C 0.9820(11) 0.5017(9) 0.9591(5) 0.0242(6) Uani 0.50 1 d P . . H18 H 1.0832 0.5390 0.9354 0.029 Uiso 0.50 1 calc PR . . O6 O 1.4620(7) 0.6521(6) 0.8306(4) 0.0240(11) Uani 0.50 1 d P . . C24 C 1.4883(10) 0.6632(8) 0.9412(6) 0.0204(9) Uani 0.50 1 d P . . O5 O 0.3635(6) 0.2832(6) 0.9933(4) 0.0474(13) Uani 0.50 1 d P . . C21 C 1.1578(7) 0.5594(6) 0.8967(5) 0.0242(6) Uani 0.50 1 d P . . H21 H 1.1506 0.5634 0.8219 0.029 Uiso 0.50 1 calc PR . . C22 C 1.3236(7) 0.6062(6) 0.9746(4) 0.0204(9) Uani 0.50 1 d P . . C20 C 0.6622(7) 0.3994(6) 0.9131(5) 0.0242(6) Uani 0.50 1 d P . . H20 H 0.5516 0.3665 0.8606 0.029 Uiso 0.50 1 calc PR . . N4 N 0.4181(8) 0.2841(7) 0.9253(6) 0.0465(13) Uani 0.50 1 d P . . C25 C 1.4128(12) 0.6273(11) 0.8652(8) 0.035(2) Uani 0.50 1 d P . . H25A H 1.4942 0.6581 0.8214 0.052 Uiso 0.50 1 calc PR . . H25B H 1.3264 0.6689 0.8455 0.052 Uiso 0.50 1 calc PR . . H25C H 1.3539 0.5210 0.8511 0.052 Uiso 0.50 1 calc PR . . C23 C 0.8249(10) 0.4616(9) 0.8473(5) 0.0242(6) Uani 0.50 1 d P . . H23A H 0.7765 0.5324 0.8604 0.036 Uiso 0.50 1 calc PR . . H23B H 0.7471 0.3654 0.8555 0.036 Uiso 0.50 1 calc PR . . H23C H 0.8365 0.4578 0.7730 0.036 Uiso 0.50 1 calc PR . . C26 C 1.5086(15) 0.6779(12) 0.9819(8) 0.0465(13) Uani 0.50 1 d P . . C19 C 1.0010(10) 0.5062(9) 0.9288(6) 0.0242(6) Uani 0.50 1 d P . . H4 H -0.206(4) 0.603(3) 0.374(2) 0.020(7) Uiso 1 1 d . . . H3 H -0.492(4) 0.582(3) 0.310(3) 0.025(8) Uiso 1 1 d . . . H13 H 0.245(4) 1.092(3) 0.709(2) 0.023(7) Uiso 1 1 d . . . H1 H -0.467(4) 0.749(3) 0.626(2) 0.019(7) Uiso 1 1 d . . . H6 H -0.084(4) 0.794(3) 1.113(2) 0.015(7) Uiso 1 1 d . . . H7 H 0.041(3) 0.822(3) 1.303(2) 0.013(6) Uiso 1 1 d . . . H5 H -0.045(4) 0.828(3) 0.928(3) 0.031(8) Uiso 1 1 d . . . H2 H -0.627(4) 0.652(3) 0.439(2) 0.029(8) Uiso 1 1 d . . . H11 H 0.248(4) 1.021(4) 0.588(3) 0.040(9) Uiso 1 1 d . . . H9 H 0.514(4) 1.014(3) 1.244(2) 0.018(7) Uiso 1 1 d . . . H12 H 0.069(4) 1.027(3) 0.603(3) 0.035(9) Uiso 1 1 d . . . H10 H 0.392(4) 0.979(4) 1.065(3) 0.037(9) Uiso 1 1 d . . . H8 H 0.357(4) 0.929(3) 1.373(3) 0.035(9) Uiso 1 1 d . . . H24 H 1.559(12) 0.699(9) 0.824(7) 0.06(3) Uiso 0.50 1 d P . . S1 S 0.06613(8) 0.72291(8) 0.58149(5) 0.0210(2) Uani 1 1 d . . . O1 O -0.2276(2) 0.7768(2) 0.79940(15) 0.0224(4) Uani 1 1 d . . . O2 O 0.3257(2) 0.9383(2) 0.90460(15) 0.0232(4) Uani 1 1 d . . . N3 N 0.0705(3) 0.8712(2) 0.95697(18) 0.0185(5) Uani 1 1 d . . . O4 O 0.1521(2) 0.7652(2) 0.49601(15) 0.0278(5) Uani 1 1 d . . . O3 O 0.0754(2) 0.6005(2) 0.63263(16) 0.0261(5) Uani 1 1 d . . . C8 C 0.0501(3) 0.8470(3) 0.7632(2) 0.0184(5) Uani 1 1 d . . . N2 N 0.3199(3) 0.9503(3) 1.11321(18) 0.0202(5) Uani 1 1 d . . . N1 N 0.1453(3) 0.8691(2) 0.68005(17) 0.0194(5) Uani 1 1 d . . . C7 C -0.1352(3) 0.7901(3) 0.7304(2) 0.0184(6) Uani 1 1 d . . . C6 C -0.2335(3) 0.7376(3) 0.6083(2) 0.0188(6) Uani 1 1 d . . . C4 C -0.2523(4) 0.6401(3) 0.4199(2) 0.0216(6) Uani 1 1 d . . . C12 C 0.0362(4) 0.8384(3) 1.1404(2) 0.0210(6) Uani 1 1 d . . . C15 C 0.3998(4) 0.9686(3) 1.2242(2) 0.0227(6) Uani 1 1 d . . . C14 C 0.3012(4) 0.9200(3) 1.2958(2) 0.0248(6) Uani 1 1 d . . . C5 C -0.1578(3) 0.6974(3) 0.5311(2) 0.0204(6) Uani 1 1 d . . . C9 C 0.1616(3) 0.8896(3) 0.8765(2) 0.0189(6) Uani 1 1 d . . . C2 C -0.5055(4) 0.6659(3) 0.4582(2) 0.0237(6) Uani 1 1 d . . . C11 C 0.1427(3) 0.8870(3) 1.0691(2) 0.0172(5) Uani 1 1 d . . . C16 C 0.1818(4) 1.0139(3) 0.6426(2) 0.0239(6) Uani 1 1 d . . . C3 C -0.4280(4) 0.6245(3) 0.3841(2) 0.0253(6) Uani 1 1 d . . . C13 C 0.1153(4) 0.8525(3) 1.2521(2) 0.0235(6) Uani 1 1 d . . . C1 C -0.4106(3) 0.7203(3) 0.5701(2) 0.0213(6) 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 C17 0.0222(12) 0.0246(11) 0.0241(18) 0.0055(13) 0.0067(12) 0.0074(9) C18 0.0222(12) 0.0246(11) 0.0241(18) 0.0055(13) 0.0067(12) 0.0074(9) O6 0.012(3) 0.034(3) 0.020(3) 0.009(2) 0.0056(19) 0.002(2) C24 0.014(2) 0.019(2) 0.026(2) 0.0045(19) 0.006(2) 0.0045(17) O5 0.011(2) 0.087(4) 0.023(2) -0.001(2) 0.0002(19) 0.002(2) C21 0.0222(12) 0.0246(11) 0.0241(18) 0.0055(13) 0.0067(12) 0.0074(9) C22 0.014(2) 0.019(2) 0.026(2) 0.0045(19) 0.006(2) 0.0045(17) C20 0.0222(12) 0.0246(11) 0.0241(18) 0.0055(13) 0.0067(12) 0.0074(9) N4 0.030(3) 0.048(3) 0.051(3) 0.003(3) 0.010(3) 0.006(2) C25 0.027(5) 0.046(5) 0.040(6) 0.015(4) 0.017(4) 0.018(4) C23 0.0222(12) 0.0246(11) 0.0241(18) 0.0055(13) 0.0067(12) 0.0074(9) C26 0.030(3) 0.048(3) 0.051(3) 0.003(3) 0.010(3) 0.006(2) C19 0.0222(12) 0.0246(11) 0.0241(18) 0.0055(13) 0.0067(12) 0.0074(9) S1 0.0128(3) 0.0279(4) 0.0187(3) 0.0011(3) 0.0026(3) 0.0061(3) O1 0.0128(9) 0.0321(11) 0.0215(10) 0.0067(8) 0.0066(8) 0.0067(8) O2 0.0100(9) 0.0326(11) 0.0194(9) 0.0005(8) 0.0022(8) 0.0022(8) N3 0.0100(11) 0.0248(12) 0.0177(11) 0.0036(9) 0.0024(9) 0.0047(10) O4 0.0182(10) 0.0416(12) 0.0197(10) 0.0026(9) 0.0063(8) 0.0078(9) O3 0.0197(10) 0.0308(11) 0.0263(10) 0.0021(9) 0.0028(8) 0.0113(9) C8 0.0143(13) 0.0206(13) 0.0190(13) 0.0036(11) 0.0055(11) 0.0052(11) N2 0.0143(11) 0.0255(12) 0.0182(11) 0.0022(10) 0.0041(10) 0.0059(10) N1 0.0128(11) 0.0231(12) 0.0173(11) 0.0012(9) 0.0028(9) 0.0034(9) C7 0.0143(13) 0.0209(13) 0.0196(13) 0.0050(11) 0.0049(11) 0.0065(11) C6 0.0142(13) 0.0171(13) 0.0195(13) 0.0042(11) 0.0021(11) 0.0018(11) C4 0.0206(14) 0.0204(14) 0.0204(14) 0.0008(11) 0.0039(12) 0.0061(12) C12 0.0129(14) 0.0235(14) 0.0237(14) 0.0039(12) 0.0056(11) 0.0043(12) C15 0.0119(14) 0.0273(15) 0.0234(14) 0.0001(12) 0.0013(11) 0.0050(12) C14 0.0217(15) 0.0310(16) 0.0181(14) 0.0030(12) 0.0030(12) 0.0086(13) C5 0.0149(13) 0.0195(13) 0.0222(14) 0.0038(11) 0.0030(11) 0.0034(11) C9 0.0141(13) 0.0184(13) 0.0208(13) 0.0026(11) 0.0044(11) 0.0034(11) C2 0.0134(13) 0.0212(14) 0.0305(15) 0.0036(12) -0.0003(12) 0.0047(12) C11 0.0147(13) 0.0170(13) 0.0179(13) 0.0011(10) 0.0031(10) 0.0058(11) C16 0.0204(15) 0.0271(15) 0.0208(14) 0.0051(13) 0.0070(12) 0.0052(13) C3 0.0211(15) 0.0245(15) 0.0204(14) 0.0003(12) -0.0045(12) 0.0057(12) C13 0.0238(15) 0.0255(15) 0.0228(14) 0.0058(12) 0.0109(12) 0.0089(12) C1 0.0149(13) 0.0209(14) 0.0248(14) 0.0053(11) 0.0043(11) 0.0042(11) _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 C17 C20 1.371(9) . ? C17 C18 1.400(9) . ? C17 H17 0.9300 . ? C18 C19 1.388(7) 2_767 ? C18 H18 0.9300 . ? O6 C24 1.340(9) . ? O6 H24 0.81(9) . ? C24 O5 1.217(9) 2_767 ? C24 C22 1.474(9) . ? C24 N4 1.624(9) 2_767 ? O5 C26 0.965(11) 2_767 ? O5 C24 1.217(9) 2_767 ? C21 C22 1.392(8) . ? C21 C19 1.404(9) . ? C21 H21 0.9300 . ? C22 C20 1.389(8) 2_767 ? C20 C22 1.389(8) 2_767 ? C20 H20 0.9300 . ? N4 C26 1.140(11) 2_767 ? N4 C24 1.624(9) 2_767 ? C25 C26 1.440(12) . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? C23 C19 1.476(9) . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C26 O5 0.965(10) 2_767 ? C26 N4 1.140(11) 2_767 ? C19 C18 1.388(7) 2_767 ? S1 O3 1.423(2) . ? S1 O4 1.437(2) . ? S1 N1 1.645(2) . ? S1 C5 1.765(3) . ? O1 C7 1.284(3) . ? O2 C9 1.239(3) . ? N3 C11 1.363(3) . ? N3 C9 1.395(3) . ? N3 H5 0.88(3) . ? C8 C7 1.397(3) . ? C8 C9 1.436(4) . ? C8 N1 1.448(3) . ? N2 C11 1.344(3) . ? N2 C15 1.359(3) . ? N2 H10 0.95(3) . ? N1 C16 1.478(4) . ? C7 C6 1.504(4) . ? C6 C5 1.399(4) . ? C6 C1 1.403(4) . ? C4 C5 1.387(4) . ? C4 C3 1.395(4) . ? C4 H4 0.90(3) . ? C12 C13 1.372(4) . ? C12 C11 1.403(4) . ? C12 H6 0.91(3) . ? C15 C14 1.362(4) . ? C15 H9 0.87(3) . ? C14 C13 1.407(4) . ? C14 H8 0.95(3) . ? C2 C3 1.384(4) . ? C2 C1 1.391(4) . ? C2 H2 0.95(3) . ? C16 H13 0.98(3) . ? C16 H11 0.98(3) . ? C16 H12 1.02(3) . ? C3 H3 0.93(3) . ? C13 H7 0.98(3) . ? C1 H1 1.02(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 C20 C17 C18 121.2(5) . . ? C20 C17 H17 119.4 . . ? C18 C17 H17 119.4 . . ? C19 C18 C17 121.0(5) 2_767 . ? C19 C18 H18 119.5 2_767 . ? C17 C18 H18 119.5 . . ? C24 O6 H24 104(6) . . ? O5 C24 O6 121.9(7) 2_767 . ? O5 C24 C22 124.0(7) 2_767 . ? O6 C24 C22 114.2(7) . . ? O6 C24 N4 161.5(7) . 2_767 ? C22 C24 N4 83.4(5) . 2_767 ? C22 C21 C19 121.4(5) . . ? C22 C21 H21 119.3 . . ? C19 C21 H21 119.3 . . ? C20 C22 C21 120.4(5) 2_767 . ? C20 C22 C24 118.2(5) 2_767 . ? C21 C22 C24 121.4(5) . . ? C17 C20 C22 118.7(6) . 2_767 ? C17 C20 H20 120.6 . . ? C22 C20 H20 120.6 2_767 . ? C26 C25 H25A 109.5 . . ? C26 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C26 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C26 C25 H24 96(3) . . ? H25B C25 H24 111.0 . . ? H25C C25 H24 120.0 . . ? C19 C23 H23A 109.5 . . ? C19 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C19 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? O5 C26 N4 60.1(7) 2_767 2_767 ? O5 C26 C25 121.0(10) 2_767 . ? N4 C26 C25 178.7(11) 2_767 . ? C18 C19 C21 117.3(5) 2_767 . ? C18 C19 C23 121.0(5) 2_767 . ? C21 C19 C23 121.7(6) . . ? O3 S1 O4 119.46(12) . . ? O3 S1 N1 108.18(11) . . ? O4 S1 N1 107.58(12) . . ? O3 S1 C5 109.50(12) . . ? O4 S1 C5 109.21(12) . . ? N1 S1 C5 101.35(12) . . ? C11 N3 C9 126.2(2) . . ? C11 N3 H5 120(2) . . ? C9 N3 H5 113(2) . . ? C7 C8 C9 125.3(2) . . ? C7 C8 N1 120.2(2) . . ? C9 C8 N1 114.5(2) . . ? C11 N2 C15 122.4(2) . . ? C11 N2 H10 119(2) . . ? C15 N2 H10 119(2) . . ? C8 N1 C16 113.8(2) . . ? C8 N1 S1 112.74(17) . . ? C16 N1 S1 116.34(18) . . ? O1 C7 C8 123.5(2) . . ? O1 C7 C6 117.7(2) . . ? C8 C7 C6 118.8(2) . . ? C5 C6 C1 118.0(2) . . ? C5 C6 C7 122.3(2) . . ? C1 C6 C7 119.5(2) . . ? C5 C4 C3 118.5(3) . . ? C5 C4 H4 120.5(18) . . ? C3 C4 H4 120.5(18) . . ? C13 C12 C11 119.3(3) . . ? C13 C12 H6 119.5(17) . . ? C11 C12 H6 121.1(17) . . ? N2 C15 C14 120.6(3) . . ? N2 C15 H9 114.6(19) . . ? C14 C15 H9 124.8(19) . . ? C15 C14 C13 118.4(3) . . ? C15 C14 H8 121(2) . . ? C13 C14 H8 121(2) . . ? C4 C5 C6 122.2(2) . . ? C4 C5 S1 120.9(2) . . ? C6 C5 S1 116.9(2) . . ? O2 C9 N3 120.5(2) . . ? O2 C9 C8 124.8(2) . . ? N3 C9 C8 114.7(2) . . ? C3 C2 C1 120.5(3) . . ? C3 C2 H2 123.7(18) . . ? C1 C2 H2 115.7(18) . . ? N2 C11 N3 119.7(2) . . ? N2 C11 C12 118.8(2) . . ? N3 C11 C12 121.5(2) . . ? N1 C16 H13 107.6(16) . . ? N1 C16 H11 108.5(19) . . ? H13 C16 H11 114(3) . . ? N1 C16 H12 113.2(18) . . ? H13 C16 H12 107(2) . . ? H11 C16 H12 106(3) . . ? C2 C3 C4 120.5(3) . . ? C2 C3 H3 121.3(18) . . ? C4 C3 H3 118.1(18) . . ? C12 C13 C14 120.4(3) . . ? C12 C13 H7 119.5(16) . . ? C14 C13 H7 119.9(15) . . ? C2 C1 C6 120.2(3) . . ? C2 C1 H1 121.5(15) . . ? C6 C1 H1 118.3(15) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.15 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.535 _refine_diff_density_min -0.397 _refine_diff_density_rms 0.077 # Attachment 'PXZ 3MBA.cif' data_shelxl_PXZ_3MBA _database_code_depnum_ccdc_archive 'CCDC 890563' #TrackingRef 'PXZ 3MBA.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H13 N3 O4 S, C8 H8 O2 ' _chemical_formula_sum 'C23 H21 N3 O6 S' _chemical_formula_weight 467.49 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 P21/c 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 9.4317(2) _cell_length_b 11.3940(3) _cell_length_c 20.4344(4) _cell_angle_alpha 90.00 _cell_angle_beta 99.9790(10) _cell_angle_gamma 90.00 _cell_volume 2162.76(8) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 87752 _cell_measurement_theta_min 1 _cell_measurement_theta_max 25.35 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.436 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 976 _exptl_absorpt_coefficient_mu 0.197 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.680 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'SADABS (Blessing, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 KappaCCD _diffrn_measurement_method 'CCD; rotation images' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 33953 _diffrn_reflns_av_R_equivalents 0.1275 _diffrn_reflns_av_sigmaI/netI 0.0615 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.02 _diffrn_reflns_theta_max 25.35 _reflns_number_total 3961 _reflns_number_gt 2830 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo&Scalepack (Otwinowski,Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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. Hydrogen refinement details: Methyl group hydrogen atoms on the 3MBA molecule were located initially using the Fourier difference synthesis and the bond distances and angles constrained to take standard values. All other H-atoms were found via the Fourier difference synthesis and allowed to refine freely. ; _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^)+(0.0450P)^2^+3.2334P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3961 _refine_ls_number_parameters 371 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0881 _refine_ls_R_factor_gt 0.0520 _refine_ls_wR_factor_ref 0.1255 _refine_ls_wR_factor_gt 0.1085 _refine_ls_goodness_of_fit_ref 0.994 _refine_ls_restrained_S_all 0.994 _refine_ls_shift/su_max 0.027 _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 H14 H 0.974(3) 0.728(3) 0.4089(15) 0.018(8) Uiso 1 1 d . . . H16 H 1.083(3) 0.577(3) 0.6237(16) 0.024(8) Uiso 1 1 d . . . H15 H 1.244(3) 0.555(3) 0.5505(14) 0.020(8) Uiso 1 1 d . . . H17 H 0.867(3) 0.680(3) 0.5865(15) 0.022(8) Uiso 1 1 d . . . H18 H 0.655(4) 0.851(3) 0.4068(18) 0.046(11) Uiso 1 1 d . . . H11 H 1.009(3) 0.118(3) 0.6795(16) 0.029(9) Uiso 1 1 d . . . H9 H 0.931(3) 0.102(3) 0.3610(14) 0.017(7) Uiso 1 1 d . . . H6 H 0.491(3) 0.185(2) 0.4271(14) 0.017(7) Uiso 1 1 d . . . H3 H 0.354(3) 0.072(3) 0.8150(14) 0.021(8) Uiso 1 1 d . . . H7 H 0.518(3) 0.225(3) 0.3173(15) 0.022(8) Uiso 1 1 d . . . H8 H 0.741(3) 0.188(3) 0.2803(17) 0.033(9) Uiso 1 1 d . . . H1 H 0.710(3) -0.136(3) 0.8466(15) 0.024(8) Uiso 1 1 d . . . H2 H 0.506(3) -0.062(3) 0.8855(16) 0.025(8) Uiso 1 1 d . . . H5 H 0.601(4) 0.105(3) 0.5335(16) 0.032(9) Uiso 1 1 d . . . H13 H 1.051(3) 0.045(3) 0.7457(16) 0.024(8) Uiso 1 1 d . . . H12 H 0.925(3) 0.134(3) 0.7400(17) 0.035(9) Uiso 1 1 d . . . H4 H 0.408(4) 0.122(3) 0.7129(18) 0.045(11) Uiso 1 1 d . . . H10 H 0.890(4) 0.066(3) 0.4600(17) 0.034(10) Uiso 1 1 d . . . O6 O 0.7474(2) 0.82630(19) 0.41503(10) 0.0255(5) Uani 1 1 d . . . O5 O 0.6672(2) 0.7761(2) 0.50799(11) 0.0431(7) Uani 1 1 d . . . C21 C 0.9337(3) 0.6709(3) 0.56006(16) 0.0248(7) Uani 1 1 d . . . C22 C 0.7619(3) 0.7754(3) 0.47496(15) 0.0239(7) Uani 1 1 d . . . C16 C 0.9025(3) 0.7152(3) 0.49579(14) 0.0212(7) Uani 1 1 d . . . C17 C 1.0001(3) 0.7003(3) 0.45230(15) 0.0206(7) Uani 1 1 d . . . C20 C 1.0612(3) 0.6107(3) 0.58019(16) 0.0266(7) Uani 1 1 d . . . C23 C 1.2321(3) 0.6207(3) 0.42450(17) 0.0352(8) Uani 1 1 d . . . H23A H 1.1896 0.6476 0.3810 0.053 Uiso 1 1 calc R . . H23B H 1.2538 0.5385 0.4227 0.053 Uiso 1 1 calc R . . H23C H 1.3192 0.6636 0.4397 0.053 Uiso 1 1 calc R . . C19 C 1.1577(3) 0.5958(3) 0.53665(16) 0.0260(7) Uani 1 1 d . . . C18 C 1.1281(3) 0.6399(3) 0.47186(15) 0.0244(7) Uani 1 1 d . . . S1 S 0.82374(8) -0.11619(6) 0.72911(4) 0.0201(2) Uani 1 1 d . . . O3 O 0.5172(2) 0.10470(19) 0.60888(10) 0.0263(5) Uani 1 1 d . . . O4 O 0.9065(2) 0.01353(18) 0.55256(10) 0.0231(5) Uani 1 1 d . . . N2 N 0.6825(3) 0.0929(2) 0.51924(12) 0.0217(6) Uani 1 1 d . . . O1 O 0.9411(2) -0.13604(18) 0.78275(10) 0.0262(5) Uani 1 1 d . . . N3 N 0.8168(3) 0.0967(2) 0.43273(12) 0.0203(6) Uani 1 1 d . . . O2 O 0.7685(2) -0.21377(17) 0.68819(10) 0.0250(5) Uani 1 1 d . . . C8 C 0.7535(3) 0.0308(2) 0.63255(14) 0.0202(6) Uani 1 1 d . . . C11 C 0.5798(3) 0.1696(3) 0.41141(15) 0.0216(7) Uani 1 1 d . . . C10 C 0.6943(3) 0.1192(3) 0.45513(14) 0.0198(6) Uani 1 1 d . . . C7 C 0.6211(3) 0.0576(3) 0.64988(14) 0.0212(7) Uani 1 1 d . . . C14 C 0.8361(3) 0.1212(3) 0.37002(15) 0.0233(7) Uani 1 1 d . . . N1 N 0.8705(2) -0.0128(2) 0.68204(11) 0.0197(5) Uani 1 1 d . . . C13 C 0.7271(3) 0.1695(3) 0.32598(15) 0.0224(7) Uani 1 1 d . . . C5 C 0.5924(3) 0.0284(2) 0.71782(14) 0.0201(6) Uani 1 1 d . . . C9 C 0.7894(3) 0.0430(2) 0.56691(14) 0.0201(6) Uani 1 1 d . . . C2 C 0.5266(3) -0.0390(3) 0.84151(16) 0.0259(7) Uani 1 1 d . . . C6 C 0.6786(3) -0.0511(3) 0.75951(14) 0.0204(7) Uani 1 1 d . . . C4 C 0.4716(3) 0.0731(3) 0.74028(15) 0.0234(7) Uani 1 1 d . . . C3 C 0.4388(3) 0.0398(3) 0.80120(16) 0.0258(7) Uani 1 1 d . . . C12 C 0.5970(3) 0.1933(3) 0.34740(15) 0.0217(7) Uani 1 1 d . . . C1 C 0.6477(3) -0.0842(3) 0.82092(15) 0.0246(7) Uani 1 1 d . . . C15 C 0.9695(4) 0.0786(3) 0.71454(17) 0.0270(7) 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 O6 0.0203(12) 0.0288(12) 0.0274(12) 0.0024(10) 0.0038(9) 0.0049(10) O5 0.0278(13) 0.0701(19) 0.0341(14) 0.0102(13) 0.0132(11) 0.0177(12) C21 0.0231(17) 0.0274(18) 0.0243(17) -0.0057(14) 0.0056(14) -0.0020(13) C22 0.0219(16) 0.0228(17) 0.0269(17) -0.0059(14) 0.0037(14) -0.0006(13) C16 0.0192(15) 0.0196(16) 0.0242(16) -0.0035(13) 0.0016(13) -0.0029(12) C17 0.0223(16) 0.0181(16) 0.0210(16) -0.0029(13) 0.0027(13) -0.0032(13) C20 0.0318(18) 0.0215(17) 0.0249(17) 0.0028(15) 0.0001(14) 0.0000(14) C23 0.0255(18) 0.037(2) 0.045(2) 0.0014(17) 0.0106(15) 0.0062(15) C19 0.0183(16) 0.0219(17) 0.0355(19) -0.0042(14) -0.0016(14) 0.0023(13) C18 0.0229(16) 0.0215(17) 0.0292(17) -0.0049(14) 0.0056(13) -0.0028(13) S1 0.0209(4) 0.0186(4) 0.0210(4) 0.0024(3) 0.0042(3) 0.0018(3) O3 0.0222(11) 0.0326(13) 0.0241(11) 0.0051(10) 0.0040(9) 0.0081(10) O4 0.0191(11) 0.0267(12) 0.0239(11) 0.0034(9) 0.0049(9) 0.0032(9) N2 0.0178(14) 0.0258(15) 0.0217(13) 0.0043(11) 0.0040(11) 0.0031(11) O1 0.0225(11) 0.0302(13) 0.0250(11) 0.0058(10) 0.0021(9) 0.0045(9) N3 0.0192(14) 0.0187(14) 0.0222(14) 0.0015(11) 0.0013(11) 0.0013(11) O2 0.0297(12) 0.0174(11) 0.0286(12) -0.0018(9) 0.0076(9) -0.0008(9) C8 0.0216(16) 0.0182(16) 0.0211(15) 0.0025(13) 0.0042(12) 0.0001(12) C11 0.0179(16) 0.0208(16) 0.0260(17) 0.0003(13) 0.0037(13) 0.0012(12) C10 0.0190(15) 0.0169(15) 0.0232(16) -0.0005(13) 0.0031(12) -0.0007(12) C7 0.0233(16) 0.0174(16) 0.0220(16) -0.0010(13) 0.0014(13) 0.0003(13) C14 0.0245(17) 0.0224(16) 0.0235(16) 0.0018(14) 0.0054(13) -0.0021(14) N1 0.0189(13) 0.0202(13) 0.0193(13) 0.0035(11) 0.0011(10) -0.0004(10) C13 0.0266(17) 0.0193(16) 0.0207(16) 0.0029(13) 0.0026(13) -0.0039(13) C5 0.0224(16) 0.0153(15) 0.0218(15) -0.0023(12) 0.0017(12) -0.0018(12) C9 0.0211(16) 0.0160(16) 0.0223(15) -0.0002(12) 0.0010(13) -0.0004(12) C2 0.0254(17) 0.0289(18) 0.0245(17) -0.0022(15) 0.0075(14) -0.0040(14) C6 0.0198(15) 0.0203(16) 0.0214(16) -0.0030(13) 0.0046(12) -0.0027(13) C4 0.0246(17) 0.0190(16) 0.0257(17) -0.0031(14) 0.0017(14) -0.0009(13) C3 0.0238(17) 0.0257(18) 0.0299(18) -0.0072(14) 0.0100(14) -0.0009(14) C12 0.0216(17) 0.0203(16) 0.0216(16) 0.0000(13) -0.0010(13) -0.0005(13) C1 0.0247(17) 0.0246(18) 0.0247(17) 0.0022(14) 0.0042(14) 0.0000(14) C15 0.0253(18) 0.0270(18) 0.0275(18) 0.0002(16) 0.0010(15) -0.0047(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 O6 C22 1.340(4) . ? O6 H18 0.90(4) . ? O5 C22 1.209(4) . ? C21 C20 1.384(4) . ? C21 C16 1.390(4) . ? C21 H17 0.90(3) . ? C22 C16 1.488(4) . ? C16 C17 1.397(4) . ? C17 C18 1.386(4) . ? C17 H14 0.93(3) . ? C20 C19 1.389(5) . ? C20 H16 0.96(3) . ? C23 C18 1.509(4) . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C19 C18 1.398(4) . ? C19 H15 0.94(3) . ? S1 O2 1.434(2) . ? S1 O1 1.434(2) . ? S1 N1 1.630(2) . ? S1 C6 1.762(3) . ? O3 C7 1.290(3) . ? O4 C9 1.237(3) . ? N2 C10 1.367(4) . ? N2 C9 1.396(4) . ? N2 H5 0.88(3) . ? N3 C10 1.339(4) . ? N3 C14 1.354(4) . ? N3 H10 0.88(4) . ? C8 C7 1.390(4) . ? C8 C9 1.446(4) . ? C8 N1 1.449(4) . ? C11 C12 1.372(4) . ? C11 C10 1.400(4) . ? C11 H6 0.97(3) . ? C7 C5 1.497(4) . ? C14 C13 1.360(4) . ? C14 H9 0.97(3) . ? N1 C15 1.477(4) . ? C13 C12 1.399(4) . ? C13 H8 0.99(3) . ? C5 C4 1.396(4) . ? C5 C6 1.403(4) . ? C2 C1 1.383(4) . ? C2 C3 1.390(5) . ? C2 H2 0.99(3) . ? C6 C1 1.389(4) . ? C4 C3 1.387(4) . ? C4 H4 0.93(4) . ? C3 H3 0.96(3) . ? C12 H7 0.95(3) . ? C1 H1 0.93(3) . ? C15 H11 0.97(3) . ? C15 H13 0.99(3) . ? C15 H12 0.96(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C22 O6 H18 104(2) . . ? C20 C21 C16 119.4(3) . . ? C20 C21 H17 122.5(19) . . ? C16 C21 H17 118.0(19) . . ? O5 C22 O6 122.6(3) . . ? O5 C22 C16 123.5(3) . . ? O6 C22 C16 113.9(2) . . ? C21 C16 C17 120.1(3) . . ? C21 C16 C22 118.0(3) . . ? C17 C16 C22 121.8(3) . . ? C18 C17 C16 120.9(3) . . ? C18 C17 H14 121.0(17) . . ? C16 C17 H14 118.0(17) . . ? C21 C20 C19 120.1(3) . . ? C21 C20 H16 120.6(18) . . ? C19 C20 H16 119.3(18) . . ? C18 C23 H23A 109.5 . . ? C18 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C18 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C20 C19 C18 121.2(3) . . ? C20 C19 H15 119.8(18) . . ? C18 C19 H15 119.0(18) . . ? C17 C18 C19 118.2(3) . . ? C17 C18 C23 121.2(3) . . ? C19 C18 C23 120.6(3) . . ? O2 S1 O1 118.54(13) . . ? O2 S1 N1 108.95(12) . . ? O1 S1 N1 108.25(12) . . ? O2 S1 C6 107.83(13) . . ? O1 S1 C6 109.91(13) . . ? N1 S1 C6 102.13(13) . . ? C10 N2 C9 126.1(3) . . ? C10 N2 H5 120(2) . . ? C9 N2 H5 114(2) . . ? C10 N3 C14 123.3(3) . . ? C10 N3 H10 119(2) . . ? C14 N3 H10 117(2) . . ? C7 C8 C9 125.5(3) . . ? C7 C8 N1 120.5(2) . . ? C9 C8 N1 114.0(2) . . ? C12 C11 C10 118.9(3) . . ? C12 C11 H6 122.2(17) . . ? C10 C11 H6 118.9(17) . . ? N3 C10 N2 120.3(3) . . ? N3 C10 C11 118.4(3) . . ? N2 C10 C11 121.3(3) . . ? O3 C7 C8 122.7(3) . . ? O3 C7 C5 117.1(2) . . ? C8 C7 C5 120.1(3) . . ? N3 C14 C13 120.0(3) . . ? N3 C14 H9 114.4(17) . . ? C13 C14 H9 125.6(17) . . ? C8 N1 C15 114.7(2) . . ? C8 N1 S1 114.06(18) . . ? C15 N1 S1 117.3(2) . . ? C14 C13 C12 118.4(3) . . ? C14 C13 H8 120.0(19) . . ? C12 C13 H8 121.7(19) . . ? C4 C5 C6 117.1(3) . . ? C4 C5 C7 120.8(3) . . ? C6 C5 C7 121.9(3) . . ? O4 C9 N2 120.8(3) . . ? O4 C9 C8 123.8(3) . . ? N2 C9 C8 115.4(3) . . ? C1 C2 C3 119.9(3) . . ? C1 C2 H2 118.8(18) . . ? C3 C2 H2 121.2(18) . . ? C1 C6 C5 122.3(3) . . ? C1 C6 S1 120.1(2) . . ? C5 C6 S1 117.5(2) . . ? C3 C4 C5 121.1(3) . . ? C3 C4 H4 119(2) . . ? C5 C4 H4 120(2) . . ? C4 C3 C2 120.4(3) . . ? C4 C3 H3 118.9(18) . . ? C2 C3 H3 120.7(18) . . ? C11 C12 C13 121.0(3) . . ? C11 C12 H7 118.8(17) . . ? C13 C12 H7 120.2(17) . . ? C2 C1 C6 119.2(3) . . ? C2 C1 H1 122.6(19) . . ? C6 C1 H1 118.2(19) . . ? N1 C15 H11 106.5(19) . . ? N1 C15 H13 112.3(18) . . ? H11 C15 H13 107(2) . . ? N1 C15 H12 114(2) . . ? H11 C15 H12 111(3) . . ? H13 C15 H12 106(3) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.305 _refine_diff_density_min -0.428 _refine_diff_density_rms 0.062 # Attachment 'PXZ 4FBA.cif' data_shelxl_PXZ_4FBA _database_code_depnum_ccdc_archive 'CCDC 890564' #TrackingRef 'PXZ 4FBA.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H13 N3 O4 S, C7 H5 F O2' _chemical_formula_sum 'C22 H18 F1 N3 O6 S' _chemical_formula_weight 471.46 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' 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.7753(3) _cell_length_b 11.4738(4) _cell_length_c 13.7702(6) _cell_angle_alpha 80.079(2) _cell_angle_beta 81.802(2) _cell_angle_gamma 76.925(2) _cell_volume 1021.12(7) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 33567 _cell_measurement_theta_min 1 _cell_measurement_theta_max 58.97 _exptl_crystal_description needles _exptl_crystal_colour yellow _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.533 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 488 _exptl_absorpt_coefficient_mu 0.216 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9170 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'SADABS (Blessing 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'Bruker Apex II CCD' _diffrn_measurement_method 'CCD; rotation images' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 33567 _diffrn_reflns_av_R_equivalents 0.0680 _diffrn_reflns_av_sigmaI/netI 0.0464 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.51 _diffrn_reflns_theta_max 29.40 _reflns_number_total 5628 _reflns_number_gt 4357 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2 (2009)' _computing_cell_refinement 'Bruker APEX2 (2009)' _computing_data_reduction 'Bruker APEX2 (2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0574P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5628 _refine_ls_number_parameters 370 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0498 _refine_ls_R_factor_gt 0.0358 _refine_ls_wR_factor_ref 0.0985 _refine_ls_wR_factor_gt 0.0930 _refine_ls_goodness_of_fit_ref 0.989 _refine_ls_restrained_S_all 0.989 _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 H7 H 0.211(2) -0.2703(14) 1.0034(11) 0.021(4) Uiso 1 1 d . . . H4 H -0.023(3) 0.6734(15) 0.6822(12) 0.025(4) Uiso 1 1 d . . . H2 H 0.327(2) 0.5666(14) 0.4346(11) 0.021(4) Uiso 1 1 d . . . H6 H 0.123(3) -0.0801(15) 0.9396(11) 0.026(4) Uiso 1 1 d . . . H10 H 0.319(2) -0.1420(13) 0.6655(11) 0.015(4) Uiso 1 1 d . . . H1 H 0.315(2) 0.3616(14) 0.5048(11) 0.019(4) Uiso 1 1 d . . . H8 H 0.367(2) -0.4167(15) 0.8997(11) 0.022(4) Uiso 1 1 d . . . H11 H 0.250(2) 0.2623(15) 0.9312(11) 0.020(4) Uiso 1 1 d . . . H5 H 0.181(3) 0.0556(16) 0.7048(13) 0.034(5) Uiso 1 1 d . . . H12 H 0.129(2) 0.3965(14) 0.9511(11) 0.022(4) Uiso 1 1 d . . . H3 H 0.161(2) 0.7214(15) 0.5257(11) 0.021(4) Uiso 1 1 d . . . H13 H 0.305(3) 0.3826(16) 0.8561(12) 0.029(4) Uiso 1 1 d . . . H9 H 0.420(2) -0.3497(15) 0.7257(11) 0.022(4) Uiso 1 1 d . . . H16 H 0.346(3) 0.8176(15) 0.3799(12) 0.026(4) Uiso 1 1 d . . . H15 H 0.255(2) 1.1690(15) 0.2539(11) 0.019(4) Uiso 1 1 d . . . H14 H 0.313(3) 1.1128(15) 0.0928(12) 0.029(4) Uiso 1 1 d . . . H17 H 0.396(3) 0.7565(16) 0.2205(12) 0.030(5) Uiso 1 1 d . . . H18 H 0.238(3) 1.1623(18) 0.4946(15) 0.046(6) Uiso 1 1 d . . . F1 F 0.40244(13) 0.89284(8) 0.05667(6) 0.0268(2) Uani 1 1 d . . . O6 O 0.24969(16) 1.14744(9) 0.43501(7) 0.0230(2) Uani 1 1 d . . . O5 O 0.25892(17) 0.95628(9) 0.50985(7) 0.0261(2) Uani 1 1 d . . . C20 C 0.3380(2) 0.87471(13) 0.32304(10) 0.0192(3) Uani 1 1 d . . . C19 C 0.2964(2) 0.99656(12) 0.33305(9) 0.0168(3) Uani 1 1 d . . . C22 C 0.2660(2) 1.03007(13) 0.43523(9) 0.0186(3) Uani 1 1 d . . . C18 C 0.2865(2) 1.08394(13) 0.24859(9) 0.0174(3) Uani 1 1 d . . . C17 C 0.3212(2) 1.04950(13) 0.15471(9) 0.0195(3) Uani 1 1 d . . . C16 C 0.3652(2) 0.92759(13) 0.14827(9) 0.0196(3) Uani 1 1 d . . . C21 C 0.3725(2) 0.83869(13) 0.22980(10) 0.0210(3) Uani 1 1 d . . . S1 S -0.11206(5) 0.46028(3) 0.79408(2) 0.01673(9) Uani 1 1 d . . . O4 O 0.06233(15) 0.09485(8) 0.92003(6) 0.0184(2) Uani 1 1 d . . . O3 O 0.19159(15) 0.19162(8) 0.61691(6) 0.0197(2) Uani 1 1 d . . . N1 N 0.02798(17) 0.33383(10) 0.84272(7) 0.0156(2) Uani 1 1 d . . . O2 O -0.12907(16) 0.54954(9) 0.85770(7) 0.0226(2) Uani 1 1 d . . . O1 O -0.29596(15) 0.43437(9) 0.77057(7) 0.0214(2) Uani 1 1 d . . . N3 N 0.18215(17) -0.13484(10) 0.89752(8) 0.0161(2) Uani 1 1 d . . . N2 N 0.16490(17) 0.02947(10) 0.76879(8) 0.0156(2) Uani 1 1 d . . . C8 C 0.0874(2) 0.24183(11) 0.77781(9) 0.0148(3) Uani 1 1 d . . . C1 C 0.0373(2) 0.49637(12) 0.68266(9) 0.0158(3) Uani 1 1 d . . . C10 C 0.2132(2) -0.09166(12) 0.80040(9) 0.0148(3) Uani 1 1 d . . . C7 C 0.1399(2) 0.27151(12) 0.67560(9) 0.0158(3) Uani 1 1 d . . . C6 C 0.0451(2) 0.61571(13) 0.64452(10) 0.0186(3) Uani 1 1 d . . . C2 C 0.1404(2) 0.39978(12) 0.63269(9) 0.0156(3) Uani 1 1 d . . . C11 C 0.3008(2) -0.17408(12) 0.73379(9) 0.0172(3) Uani 1 1 d . . . C9 C 0.1002(2) 0.11996(12) 0.82868(9) 0.0153(3) Uani 1 1 d . . . C4 C 0.2513(2) 0.54696(13) 0.50003(10) 0.0197(3) Uani 1 1 d . . . C3 C 0.2472(2) 0.42756(13) 0.53978(9) 0.0177(3) Uani 1 1 d . . . C15 C 0.1902(2) 0.34664(13) 0.89995(10) 0.0215(3) Uani 1 1 d . . . C14 C 0.2373(2) -0.25384(12) 0.93421(10) 0.0191(3) Uani 1 1 d . . . C5 C 0.1537(2) 0.64086(13) 0.55246(10) 0.0204(3) Uani 1 1 d . . . C13 C 0.3288(2) -0.33551(13) 0.87216(10) 0.0206(3) Uani 1 1 d . . . C12 C 0.3593(2) -0.29438(13) 0.77012(10) 0.0194(3) 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 F1 0.0269(5) 0.0373(5) 0.0188(4) -0.0141(4) -0.0003(3) -0.0056(4) O6 0.0343(6) 0.0189(5) 0.0145(4) -0.0044(4) -0.0029(4) -0.0011(4) O5 0.0372(6) 0.0237(6) 0.0150(4) 0.0011(4) -0.0020(4) -0.0051(5) C20 0.0191(7) 0.0195(7) 0.0180(6) -0.0015(5) -0.0001(5) -0.0041(6) C19 0.0155(6) 0.0193(7) 0.0152(6) -0.0028(5) -0.0008(5) -0.0029(5) C22 0.0185(7) 0.0198(7) 0.0158(6) -0.0029(5) -0.0017(5) -0.0001(5) C18 0.0167(7) 0.0179(7) 0.0170(6) -0.0027(5) -0.0015(5) -0.0023(5) C17 0.0166(7) 0.0261(8) 0.0149(6) -0.0019(5) -0.0020(5) -0.0030(6) C16 0.0155(7) 0.0282(8) 0.0173(6) -0.0099(5) -0.0006(5) -0.0047(6) C21 0.0184(7) 0.0204(7) 0.0253(7) -0.0082(6) 0.0015(5) -0.0050(6) S1 0.01881(18) 0.01249(16) 0.01708(15) -0.00231(11) 0.00084(12) -0.00111(12) O4 0.0237(5) 0.0152(5) 0.0142(4) -0.0010(3) 0.0011(4) -0.0026(4) O3 0.0281(6) 0.0151(5) 0.0147(4) -0.0037(4) -0.0012(4) -0.0015(4) N1 0.0212(6) 0.0114(5) 0.0130(5) -0.0022(4) -0.0010(4) -0.0011(4) O2 0.0304(6) 0.0152(5) 0.0202(4) -0.0053(4) 0.0016(4) -0.0012(4) O1 0.0178(5) 0.0172(5) 0.0269(5) -0.0021(4) -0.0001(4) -0.0010(4) N3 0.0186(6) 0.0141(6) 0.0143(5) -0.0023(4) -0.0006(4) -0.0013(4) N2 0.0189(6) 0.0127(5) 0.0139(5) -0.0017(4) -0.0013(4) -0.0012(4) C8 0.0160(6) 0.0124(6) 0.0151(5) -0.0035(5) -0.0002(5) -0.0011(5) C1 0.0153(6) 0.0163(7) 0.0152(5) -0.0007(5) -0.0023(5) -0.0028(5) C10 0.0140(6) 0.0143(6) 0.0160(6) -0.0016(5) -0.0027(5) -0.0027(5) C7 0.0150(6) 0.0157(6) 0.0162(6) -0.0023(5) -0.0029(5) -0.0013(5) C6 0.0196(7) 0.0148(7) 0.0207(6) -0.0010(5) -0.0045(5) -0.0017(5) C2 0.0155(6) 0.0158(6) 0.0152(5) -0.0012(5) -0.0040(5) -0.0022(5) C11 0.0191(7) 0.0171(7) 0.0155(6) -0.0029(5) -0.0017(5) -0.0033(5) C9 0.0142(6) 0.0150(6) 0.0165(6) -0.0031(5) -0.0012(5) -0.0022(5) C4 0.0170(7) 0.0234(7) 0.0177(6) 0.0029(5) -0.0029(5) -0.0061(6) C3 0.0153(7) 0.0203(7) 0.0166(6) -0.0008(5) -0.0026(5) -0.0025(5) C15 0.0275(8) 0.0182(7) 0.0197(6) -0.0051(5) -0.0057(6) -0.0029(6) C14 0.0238(7) 0.0151(7) 0.0170(6) 0.0007(5) -0.0024(5) -0.0033(5) C5 0.0209(7) 0.0170(7) 0.0227(6) 0.0036(5) -0.0054(5) -0.0055(6) C13 0.0255(8) 0.0127(7) 0.0221(6) -0.0005(5) -0.0040(5) -0.0014(6) C12 0.0210(7) 0.0165(7) 0.0209(6) -0.0066(5) -0.0020(5) -0.0016(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_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F1 C16 1.3604(14) . ? O6 C22 1.3256(17) . ? O6 H18 0.86(2) . ? O5 C22 1.2164(16) . ? C20 C21 1.3883(18) . ? C20 C19 1.3892(19) . ? C20 H16 0.930(16) . ? C19 C18 1.3973(18) . ? C19 C22 1.4959(17) . ? C18 C17 1.3891(17) . ? C18 H15 0.964(16) . ? C17 C16 1.378(2) . ? C17 H14 1.020(16) . ? C16 C21 1.379(2) . ? C21 H17 0.949(17) . ? S1 O2 1.4341(10) . ? S1 O1 1.4358(10) . ? S1 N1 1.6363(11) . ? S1 C1 1.7543(13) . ? O4 C9 1.2441(15) . ? O3 C7 1.2826(15) . ? N1 C8 1.4510(15) . ? N1 C15 1.4869(17) . ? N3 C10 1.3479(16) . ? N3 C14 1.3582(17) . ? N3 H6 0.915(17) . ? N2 C10 1.3618(16) . ? N2 C9 1.3916(16) . ? N2 H5 0.880(17) . ? C8 C7 1.4038(17) . ? C8 C9 1.4417(18) . ? C1 C6 1.3895(19) . ? C1 C2 1.4016(18) . ? C10 C11 1.4063(17) . ? C7 C2 1.4890(19) . ? C6 C5 1.3913(19) . ? C6 H4 0.912(17) . ? C2 C3 1.4008(18) . ? C11 C12 1.3724(19) . ? C11 H10 0.950(14) . ? C4 C5 1.389(2) . ? C4 C3 1.390(2) . ? C4 H2 0.988(16) . ? C3 H1 0.959(15) . ? C15 H11 1.007(16) . ? C15 H12 0.971(16) . ? C15 H13 1.031(18) . ? C14 C13 1.3618(19) . ? C14 H7 0.938(15) . ? C5 H3 0.944(17) . ? C13 C12 1.4045(18) . ? C13 H8 0.936(16) . ? C12 H9 0.944(16) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C22 O6 H18 109.9(13) . . ? C21 C20 C19 120.65(13) . . ? C21 C20 H16 120.5(10) . . ? C19 C20 H16 118.8(10) . . ? C20 C19 C18 119.78(12) . . ? C20 C19 C22 118.37(12) . . ? C18 C19 C22 121.85(12) . . ? O5 C22 O6 124.30(12) . . ? O5 C22 C19 122.90(13) . . ? O6 C22 C19 112.79(11) . . ? C17 C18 C19 120.33(13) . . ? C17 C18 H15 118.6(9) . . ? C19 C18 H15 121.1(9) . . ? C16 C17 C18 117.90(13) . . ? C16 C17 H14 121.4(9) . . ? C18 C17 H14 120.7(9) . . ? F1 C16 C17 118.39(12) . . ? F1 C16 C21 118.09(13) . . ? C17 C16 C21 123.52(12) . . ? C16 C21 C20 117.79(13) . . ? C16 C21 H17 119.5(10) . . ? C20 C21 H17 122.7(10) . . ? O2 S1 O1 118.35(6) . . ? O2 S1 N1 108.49(5) . . ? O1 S1 N1 108.33(6) . . ? O2 S1 C1 110.23(6) . . ? O1 S1 C1 108.29(6) . . ? N1 S1 C1 101.89(6) . . ? C8 N1 C15 115.45(10) . . ? C8 N1 S1 114.25(8) . . ? C15 N1 S1 115.82(9) . . ? C10 N3 C14 122.93(11) . . ? C10 N3 H6 117.3(10) . . ? C14 N3 H6 119.8(10) . . ? C10 N2 C9 126.27(11) . . ? C10 N2 H5 118.8(12) . . ? C9 N2 H5 114.8(12) . . ? C7 C8 C9 124.24(11) . . ? C7 C8 N1 121.54(11) . . ? C9 C8 N1 114.09(10) . . ? C6 C1 C2 122.13(12) . . ? C6 C1 S1 121.07(10) . . ? C2 C1 S1 116.76(10) . . ? N3 C10 N2 120.20(11) . . ? N3 C10 C11 118.46(12) . . ? N2 C10 C11 121.32(11) . . ? O3 C7 C8 122.47(12) . . ? O3 C7 C2 117.98(11) . . ? C8 C7 C2 119.53(11) . . ? C1 C6 C5 119.14(13) . . ? C1 C6 H4 117.0(11) . . ? C5 C6 H4 123.8(11) . . ? C3 C2 C1 117.60(12) . . ? C3 C2 C7 120.22(12) . . ? C1 C2 C7 122.18(12) . . ? C12 C11 C10 119.11(12) . . ? C12 C11 H10 123.7(9) . . ? C10 C11 H10 117.2(9) . . ? O4 C9 N2 121.10(12) . . ? O4 C9 C8 123.49(11) . . ? N2 C9 C8 115.38(11) . . ? C5 C4 C3 120.77(13) . . ? C5 C4 H2 118.6(9) . . ? C3 C4 H2 120.6(9) . . ? C4 C3 C2 120.56(13) . . ? C4 C3 H1 121.8(9) . . ? C2 C3 H1 117.6(9) . . ? N1 C15 H11 105.9(9) . . ? N1 C15 H12 109.0(9) . . ? H11 C15 H12 110.0(12) . . ? N1 C15 H13 113.1(9) . . ? H11 C15 H13 108.6(13) . . ? H12 C15 H13 110.2(13) . . ? N3 C14 C13 120.09(12) . . ? N3 C14 H7 113.6(10) . . ? C13 C14 H7 126.3(10) . . ? C4 C5 C6 119.75(13) . . ? C4 C5 H3 120.1(10) . . ? C6 C5 H3 120.2(9) . . ? C14 C13 C12 118.64(13) . . ? C14 C13 H8 118.2(10) . . ? C12 C13 H8 123.2(10) . . ? C11 C12 C13 120.71(12) . . ? C11 C12 H9 119.3(10) . . ? C13 C12 H9 120.0(10) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 29.40 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.486 _refine_diff_density_min -0.367 _refine_diff_density_rms 0.058 # Attachment 'PXZ 4MBA.cif' data_shelxl_PXZ_4MBA _database_code_depnum_ccdc_archive 'CCDC 890565' #TrackingRef 'PXZ 4MBA.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H13 N3 O4 S, C8 H8 O2' _chemical_formula_sum 'C23 H21 N3 O6 S' _chemical_formula_weight 467.49 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' 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' N N 0.0061 0.0033 '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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.5744(12) _cell_length_b 10.4949(16) _cell_length_c 12.5497(16) _cell_angle_alpha 66.362(5) _cell_angle_beta 73.077(4) _cell_angle_gamma 75.292(5) _cell_volume 1091.6(3) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.422 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 488 _exptl_absorpt_coefficient_mu 0.195 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4814 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'ABSCOR, Rigaku 1995' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 R-AXIS RAPID IP Image Plate diffractometer' _diffrn_measurement_method 'image plate' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11677 _diffrn_reflns_av_R_equivalents 0.0829 _diffrn_reflns_av_sigmaI/netI 0.0916 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.18 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4676 _reflns_number_gt 2837 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear 1.4.0 (Rigaku, 2008)' _computing_cell_refinement 'CrystalClear 1.4.0 (Rigaku, 2008)' _computing_data_reduction 'CrystalClear 1.4.0 (Rigaku, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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. Hydrogen refinement details: Methyl group hydrogen atoms on the 4MBA molecule were located initially using the Fourier difference synthesis and the bond distances and angles constrained to take standard values. All other H-atoms were found via the Fourier difference synthesis and allowed to refine freely. ; _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^)+(0.0678P)^2^+0.2665P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4676 _refine_ls_number_parameters 371 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1177 _refine_ls_R_factor_gt 0.0651 _refine_ls_wR_factor_ref 0.1605 _refine_ls_wR_factor_gt 0.1345 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _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 H4 H -0.064(3) -0.389(3) 1.618(2) 0.018(8) Uiso 1 1 d . . . H1 H -0.306(4) 0.004(4) 1.342(3) 0.034(9) Uiso 1 1 d . . . H11 H 0.382(3) 0.382(3) 0.604(3) 0.023(8) Uiso 1 1 d . . . H10 H 0.124(3) 0.408(3) 0.661(3) 0.025(8) Uiso 1 1 d . . . H13 H 0.412(4) 0.098(4) 0.924(3) 0.052(11) Uiso 1 1 d . . . H12 H 0.531(3) 0.220(3) 0.735(3) 0.022(8) Uiso 1 1 d . . . H5 H 0.142(4) -0.007(4) 1.423(3) 0.051(11) Uiso 1 1 d . . . H9 H 0.019(4) 0.278(3) 0.859(3) 0.028(9) Uiso 1 1 d . . . H7 H 0.303(4) 0.003(4) 1.325(3) 0.048(11) Uiso 1 1 d . . . H2 H -0.445(4) -0.122(3) 1.536(3) 0.039(10) Uiso 1 1 d . . . H3 H -0.325(4) -0.319(3) 1.671(3) 0.034(9) Uiso 1 1 d . . . H6 H 0.300(3) -0.133(3) 1.444(3) 0.030(9) Uiso 1 1 d . . . H8 H 0.050(4) 0.104(4) 1.045(3) 0.039(10) Uiso 1 1 d . . . H17 H 0.519(4) 0.459(4) 0.254(3) 0.043(10) Uiso 1 1 d . . . H15 H 0.729(3) 0.689(3) -0.146(3) 0.026(8) Uiso 1 1 d . . . H16 H 0.378(4) 0.632(4) 0.125(3) 0.046(11) Uiso 1 1 d . . . H14 H 0.882(4) 0.516(3) -0.023(3) 0.034(9) Uiso 1 1 d . . . H18 H 0.247(5) 0.880(5) -0.110(4) 0.077(15) Uiso 1 1 d . . . S1 S 0.14999(8) -0.29019(8) 1.39709(7) 0.0259(2) Uani 1 1 d . . . O2 O -0.0984(2) 0.0382(2) 1.16563(18) 0.0279(5) Uani 1 1 d . . . O1 O 0.3617(2) -0.0062(2) 1.09129(17) 0.0266(5) Uani 1 1 d . . . N1 N 0.3553(3) 0.1625(3) 0.8679(2) 0.0230(6) Uani 1 1 d . . . O3 O 0.1609(2) -0.3629(2) 1.31839(18) 0.0292(5) Uani 1 1 d . . . N3 N 0.2100(3) -0.1407(3) 1.3175(2) 0.0223(6) Uani 1 1 d . . . O4 O 0.2223(2) -0.3604(2) 1.49602(18) 0.0322(6) Uani 1 1 d . . . N2 N 0.1488(3) 0.1017(3) 1.0225(2) 0.0233(6) Uani 1 1 d . . . C6 C -0.1068(3) -0.1153(3) 1.3666(3) 0.0232(7) Uani 1 1 d . . . C8 C -0.0225(3) -0.0382(3) 1.2457(3) 0.0242(7) Uani 1 1 d . . . C10 C 0.2077(3) 0.1773(3) 0.9078(3) 0.0247(7) Uani 1 1 d . . . C13 C 0.3379(4) 0.3274(3) 0.6769(3) 0.0279(8) Uani 1 1 d . . . C14 C 0.4213(4) 0.2353(3) 0.7552(3) 0.0261(7) Uani 1 1 d . . . C3 C -0.2665(4) -0.2648(3) 1.5915(3) 0.0286(8) Uani 1 1 d . . . C9 C 0.2253(3) 0.0113(3) 1.1109(3) 0.0236(7) Uani 1 1 d . . . C1 C -0.2592(3) -0.0743(3) 1.4007(3) 0.0265(7) Uani 1 1 d . . . C7 C 0.1305(3) -0.0536(3) 1.2237(2) 0.0231(7) Uani 1 1 d . . . C11 C 0.1184(4) 0.2712(3) 0.8287(3) 0.0260(7) Uani 1 1 d . . . C12 C 0.1833(4) 0.3446(3) 0.7147(3) 0.0264(7) Uani 1 1 d . . . C15 C 0.2424(4) -0.0639(4) 1.3824(3) 0.0291(8) Uani 1 1 d . . . C4 C -0.1156(3) -0.3078(3) 1.5593(3) 0.0278(7) Uani 1 1 d . . . C5 C -0.0377(3) -0.2344(3) 1.4478(3) 0.0252(7) Uani 1 1 d . . . C2 C -0.3368(4) -0.1487(3) 1.5120(3) 0.0287(8) Uani 1 1 d . . . O5 O 0.4882(2) 0.8402(2) -0.21129(19) 0.0344(6) Uani 1 1 d . . . O6 O 0.3037(2) 0.8152(2) -0.0501(2) 0.0325(6) Uani 1 1 d . . . C21 C 0.5626(4) 0.5071(4) 0.1704(3) 0.0316(8) Uani 1 1 d . . . C19 C 0.5353(4) 0.6787(3) -0.0220(3) 0.0266(7) Uani 1 1 d . . . C17 C 0.7724(4) 0.5416(4) 0.0081(3) 0.0348(8) Uani 1 1 d . . . C18 C 0.6851(4) 0.6447(4) -0.0656(3) 0.0309(8) Uani 1 1 d . . . C23 C 0.4427(3) 0.7857(3) -0.1039(3) 0.0267(7) Uani 1 1 d . . . C20 C 0.4740(4) 0.6090(4) 0.0973(3) 0.0298(8) Uani 1 1 d . . . C16 C 0.7130(4) 0.4715(3) 0.1275(3) 0.0322(8) Uani 1 1 d . . . C22 C 0.8080(4) 0.3579(4) 0.2082(3) 0.0445(10) Uani 1 1 d . . . H22A H 0.7981 0.3797 0.2776 0.067 Uiso 1 1 calc R . . H22B H 0.9095 0.3532 0.1664 0.067 Uiso 1 1 calc R . . H22C H 0.7766 0.2688 0.2317 0.067 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 0.0249(4) 0.0232(4) 0.0221(4) -0.0020(3) -0.0007(3) -0.0064(3) O2 0.0270(12) 0.0276(12) 0.0219(11) -0.0020(10) -0.0040(10) -0.0048(9) O1 0.0231(11) 0.0286(12) 0.0225(11) -0.0034(9) -0.0021(9) -0.0071(9) N1 0.0250(14) 0.0229(14) 0.0183(13) -0.0027(11) -0.0041(11) -0.0073(11) O3 0.0304(12) 0.0255(12) 0.0288(12) -0.0110(10) -0.0001(10) -0.0046(10) N3 0.0246(14) 0.0215(13) 0.0164(12) -0.0002(10) -0.0030(11) -0.0089(11) O4 0.0325(13) 0.0305(13) 0.0226(11) 0.0039(10) -0.0067(10) -0.0077(10) N2 0.0217(14) 0.0250(14) 0.0175(13) -0.0023(11) -0.0015(11) -0.0058(11) C6 0.0274(17) 0.0212(15) 0.0188(15) -0.0064(13) 0.0010(13) -0.0083(13) C8 0.0313(17) 0.0182(15) 0.0204(15) -0.0057(13) -0.0016(14) -0.0057(13) C10 0.0261(17) 0.0225(16) 0.0242(16) -0.0081(13) -0.0013(14) -0.0070(13) C13 0.0366(19) 0.0235(17) 0.0204(17) -0.0018(14) -0.0061(15) -0.0093(15) C14 0.0272(18) 0.0240(16) 0.0251(17) -0.0077(14) 0.0018(14) -0.0107(14) C3 0.0314(18) 0.0284(18) 0.0221(17) -0.0058(14) 0.0012(14) -0.0113(14) C9 0.0277(17) 0.0219(16) 0.0201(15) -0.0049(13) -0.0034(14) -0.0082(13) C1 0.0269(17) 0.0260(17) 0.0235(17) -0.0071(14) -0.0021(14) -0.0055(14) C7 0.0251(16) 0.0250(16) 0.0160(15) -0.0035(13) -0.0032(13) -0.0059(13) C11 0.0248(17) 0.0243(17) 0.0268(17) -0.0065(14) -0.0030(14) -0.0072(14) C12 0.0308(18) 0.0231(16) 0.0250(17) -0.0051(14) -0.0085(15) -0.0066(14) C15 0.0309(19) 0.0317(19) 0.0251(18) -0.0080(16) -0.0068(16) -0.0082(16) C4 0.0255(17) 0.0266(17) 0.0249(17) -0.0056(14) 0.0011(14) -0.0068(14) C5 0.0272(16) 0.0213(16) 0.0255(17) -0.0072(13) -0.0024(14) -0.0068(13) C2 0.0235(17) 0.0308(18) 0.0296(18) -0.0102(15) -0.0010(14) -0.0066(14) O5 0.0315(13) 0.0389(14) 0.0263(13) -0.0055(11) -0.0038(10) -0.0073(11) O6 0.0260(12) 0.0394(14) 0.0275(13) -0.0111(11) -0.0047(11) -0.0002(10) C21 0.037(2) 0.0341(19) 0.0265(18) -0.0089(16) -0.0074(16) -0.0118(16) C19 0.0308(18) 0.0242(17) 0.0275(17) -0.0086(14) -0.0104(14) -0.0050(14) C17 0.0297(19) 0.036(2) 0.039(2) -0.0152(17) -0.0086(17) -0.0016(16) C18 0.0293(18) 0.038(2) 0.0246(18) -0.0104(16) -0.0008(15) -0.0108(15) C23 0.0273(18) 0.0292(17) 0.0273(18) -0.0122(15) -0.0055(15) -0.0075(14) C20 0.0267(18) 0.0303(18) 0.0322(19) -0.0095(15) -0.0052(16) -0.0080(15) C16 0.042(2) 0.0233(17) 0.038(2) -0.0111(15) -0.0174(17) -0.0056(15) C22 0.055(2) 0.033(2) 0.050(2) -0.0116(18) -0.026(2) -0.0022(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 O3 1.439(2) . ? S1 O4 1.439(2) . ? S1 N3 1.629(2) . ? S1 C5 1.754(3) . ? O2 C8 1.290(3) . ? O1 C9 1.235(3) . ? N1 C10 1.345(4) . ? N1 C14 1.358(4) . ? N1 H13 0.95(4) . ? N3 C7 1.451(4) . ? N3 C15 1.486(4) . ? N2 C10 1.364(4) . ? N2 C9 1.394(4) . ? N2 H8 0.91(3) . ? C6 C1 1.401(4) . ? C6 C5 1.411(4) . ? C6 C8 1.498(4) . ? C8 C7 1.389(4) . ? C10 C11 1.403(4) . ? C13 C14 1.357(4) . ? C13 C12 1.405(4) . ? C13 H11 0.91(3) . ? C14 H12 1.00(3) . ? C3 C4 1.389(4) . ? C3 C2 1.390(4) . ? C3 H3 1.01(3) . ? C9 C7 1.444(4) . ? C1 C2 1.388(4) . ? C1 H1 0.97(3) . ? C11 C12 1.367(4) . ? C11 H9 0.91(3) . ? C12 H10 0.94(3) . ? C15 H5 1.10(4) . ? C15 H7 0.95(4) . ? C15 H6 1.01(3) . ? C4 C5 1.388(4) . ? C4 H4 1.01(3) . ? C2 H2 0.99(3) . ? O5 C23 1.224(4) . ? O6 C23 1.326(4) . ? O6 H18 0.98(4) . ? C21 C20 1.383(5) . ? C21 C16 1.393(5) . ? C21 H17 0.98(3) . ? C19 C18 1.386(4) . ? C19 C20 1.396(4) . ? C19 C23 1.485(4) . ? C17 C18 1.383(5) . ? C17 C16 1.394(5) . ? C17 H14 1.02(3) . ? C18 H15 0.94(3) . ? C20 H16 0.89(4) . ? C16 C22 1.513(4) . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? 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 O3 S1 O4 118.70(14) . . ? O3 S1 N3 108.16(13) . . ? O4 S1 N3 108.56(13) . . ? O3 S1 C5 108.25(15) . . ? O4 S1 C5 110.01(14) . . ? N3 S1 C5 101.83(14) . . ? C10 N1 C14 122.9(3) . . ? C10 N1 H13 116(2) . . ? C14 N1 H13 121(2) . . ? C7 N3 C15 115.0(2) . . ? C7 N3 S1 112.90(19) . . ? C15 N3 S1 117.2(2) . . ? C10 N2 C9 127.2(3) . . ? C10 N2 H8 119(2) . . ? C9 N2 H8 114(2) . . ? C1 C6 C5 117.8(3) . . ? C1 C6 C8 120.6(3) . . ? C5 C6 C8 121.5(3) . . ? O2 C8 C7 123.3(3) . . ? O2 C8 C6 116.8(3) . . ? C7 C8 C6 119.8(3) . . ? N1 C10 N2 119.8(3) . . ? N1 C10 C11 118.4(3) . . ? N2 C10 C11 121.8(3) . . ? C14 C13 C12 118.8(3) . . ? C14 C13 H11 120.0(19) . . ? C12 C13 H11 121.0(19) . . ? C13 C14 N1 120.1(3) . . ? C13 C14 H12 123.1(17) . . ? N1 C14 H12 116.8(17) . . ? C4 C3 C2 119.6(3) . . ? C4 C3 H3 120.3(18) . . ? C2 C3 H3 120.1(18) . . ? O1 C9 N2 121.1(3) . . ? O1 C9 C7 125.1(3) . . ? N2 C9 C7 113.8(3) . . ? C2 C1 C6 120.1(3) . . ? C2 C1 H1 123(2) . . ? C6 C1 H1 117(2) . . ? C8 C7 C9 125.5(3) . . ? C8 C7 N3 120.8(2) . . ? C9 C7 N3 113.7(2) . . ? C12 C11 C10 119.4(3) . . ? C12 C11 H9 124.7(19) . . ? C10 C11 H9 115.9(19) . . ? C11 C12 C13 120.5(3) . . ? C11 C12 H10 119.8(18) . . ? C13 C12 H10 119.7(18) . . ? N3 C15 H5 112.7(19) . . ? N3 C15 H7 107(2) . . ? H5 C15 H7 108(3) . . ? N3 C15 H6 108.6(18) . . ? H5 C15 H6 111(3) . . ? H7 C15 H6 109(3) . . ? C5 C4 C3 119.3(3) . . ? C5 C4 H4 120.9(16) . . ? C3 C4 H4 119.7(16) . . ? C4 C5 C6 121.9(3) . . ? C4 C5 S1 121.8(2) . . ? C6 C5 S1 116.2(2) . . ? C1 C2 C3 121.4(3) . . ? C1 C2 H2 120.6(19) . . ? C3 C2 H2 118.0(19) . . ? C23 O6 H18 109(3) . . ? C20 C21 C16 121.3(3) . . ? C20 C21 H17 119(2) . . ? C16 C21 H17 119(2) . . ? C18 C19 C20 119.3(3) . . ? C18 C19 C23 119.3(3) . . ? C20 C19 C23 121.3(3) . . ? C18 C17 C16 121.1(3) . . ? C18 C17 H14 120.8(18) . . ? C16 C17 H14 118.2(18) . . ? C17 C18 C19 120.3(3) . . ? C17 C18 H15 118.4(19) . . ? C19 C18 H15 121.2(19) . . ? O5 C23 O6 122.7(3) . . ? O5 C23 C19 123.8(3) . . ? O6 C23 C19 113.5(3) . . ? C21 C20 C19 119.9(3) . . ? C21 C20 H16 121(2) . . ? C19 C20 H16 119(2) . . ? C21 C16 C17 118.1(3) . . ? C21 C16 C22 120.7(3) . . ? C17 C16 C22 121.2(3) . . ? C16 C22 H22A 109.5 . . ? C16 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C16 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.933 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.951 _refine_diff_density_max 0.326 _refine_diff_density_min -0.600 _refine_diff_density_rms 0.071