# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2010 data_global _publ_contact_author ; B. Kariuki, School of Chemistry, Cardiff University, Main Building Park Place Cardiff CF10 3AT ; _publ_contact_author_email kariukib@cardiff.ac.uk _publ_section_title ; <> ; _publ_section_references ; SHELX97 [Includes SHELXS97, SHELXL97, CIFTAB] - Programs for Crystal Structure Analysis (Release 97-2). G. M. Sheldrick, Instit t f r Anorganische Chemie der Universitat, Tammanstrasse 4, D-3400 G ttingen, Germany, 1998. DENZO-SCALEPACK Z. Otwinowski and W. Minor, " Processing of X-ray Diffraction Data Collected in Oscillation Mode ", Methods in Enzymology, Volume 276: Macromolecular Crystallography, part A, p.307-326, 1997,C.W. Carter, Jr. & R. M. Sweet, Eds., Academic Press. ; data_gjh0807dt _database_code_depnum_ccdc_archive 'CCDC 791821' #TrackingRef 'gjh0807dt.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H12 N2 O4 S' _chemical_formula_sum 'C14 H12 N2 O4 S' _chemical_formula_weight 304.32 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 6.7710(3) _cell_length_b 26.8040(15) _cell_length_c 7.4480(3) _cell_angle_alpha 90.00 _cell_angle_beta 89.867(3) _cell_angle_gamma 90.00 _cell_volume 1351.73(11) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.495 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 632 _exptl_absorpt_coefficient_mu 0.257 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9385 _exptl_absorpt_correction_T_max 0.9923 _exptl_absorpt_process_details Denzo/Scalepack _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 'Nonius KappaCCD' _diffrn_measurement_method 'CCD scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6362 _diffrn_reflns_av_R_equivalents 0.0578 _diffrn_reflns_av_sigmaI/netI 0.1068 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 34 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 2.73 _diffrn_reflns_theta_max 27.39 _reflns_number_total 4274 _reflns_number_gt 3448 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'cOLLECT,Nonius BV, 1997-2001' _computing_cell_refinement DENZO/SCALEPACK _computing_data_reduction DENZO/SCALEPACK _computing_structure_solution SHELXs-97 _computing_structure_refinement SHELXL-97 _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^)+(0.0659P)^2^+11.3973P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.0(2) _refine_ls_number_reflns 4274 _refine_ls_number_parameters 379 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1178 _refine_ls_R_factor_gt 0.0964 _refine_ls_wR_factor_ref 0.2350 _refine_ls_wR_factor_gt 0.2224 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.061 _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 C1 C 0.6374(14) 0.4634(4) -0.4924(13) 0.020(2) Uani 1 1 d . . . C2 C 0.6174(13) 0.4471(4) -0.6710(13) 0.020(2) Uani 1 1 d . . . H2 H 0.6223 0.4701 -0.7680 0.024 Uiso 1 1 calc R . . C3 C 0.5902(15) 0.3962(5) -0.7010(17) 0.034(3) Uani 1 1 d . . . H3 H 0.5721 0.3849 -0.8206 0.041 Uiso 1 1 calc R . . C4 C 0.5888(16) 0.3622(4) -0.5645(17) 0.036(3) Uani 1 1 d . . . H4 H 0.5760 0.3276 -0.5908 0.043 Uiso 1 1 calc R . . C5 C 0.6059(15) 0.3778(4) -0.3869(18) 0.034(3) Uani 1 1 d . . . H5 H 0.6028 0.3545 -0.2908 0.040 Uiso 1 1 calc R . . C6 C 0.6279(14) 0.4288(4) -0.3545(15) 0.027(2) Uani 1 1 d . . . H6 H 0.6367 0.4401 -0.2339 0.032 Uiso 1 1 calc R . . C7 C 0.6604(13) 0.5165(4) -0.4466(13) 0.024(2) Uani 1 1 d . . . H7 H 0.6146 0.5259 -0.3234 0.028 Uiso 1 1 calc R . . C8 C 0.8187(13) 0.5490(4) -0.5232(13) 0.019(2) Uani 1 1 d . . . H8A H 0.9181 0.5332 -0.6026 0.022 Uiso 1 1 calc R . . H8B H 0.8702 0.5763 -0.4469 0.022 Uiso 1 1 calc R . . C9 C 0.5454(14) 0.6499(4) -0.6676(13) 0.018(2) Uani 1 1 d . . . C10 C 0.5326(13) 0.6392(4) -0.8544(12) 0.017(2) Uani 1 1 d . . . H10 H 0.5100 0.6061 -0.8946 0.020 Uiso 1 1 calc R . . C11 C 0.5539(12) 0.6782(4) -0.9782(13) 0.016(2) Uani 1 1 d . . . H11 H 0.5489 0.6724 -1.1039 0.019 Uiso 1 1 calc R . . C12 C 0.5825(14) 0.7257(3) -0.9095(12) 0.017(2) Uani 1 1 d . . . C13 C 0.5952(15) 0.7371(4) -0.7307(15) 0.027(2) Uani 1 1 d . . . H13 H 0.6144 0.7706 -0.6927 0.033 Uiso 1 1 calc R . . C14 C 0.5791(14) 0.6982(4) -0.6045(13) 0.024(2) Uani 1 1 d . . . H14 H 0.5908 0.7047 -0.4796 0.028 Uiso 1 1 calc R . . C15 C 0.0616(13) 0.6508(4) 0.0077(12) 0.016(2) Uani 1 1 d . . . C16 C 0.0664(16) 0.6680(4) -0.1682(15) 0.031(3) Uani 1 1 d . . . H16 H 0.0608 0.6450 -0.2650 0.038 Uiso 1 1 calc R . . C17 C 0.0790(15) 0.7179(4) -0.2021(17) 0.033(3) Uani 1 1 d . . . H17 H 0.0788 0.7290 -0.3233 0.039 Uiso 1 1 calc R . . C18 C 0.0919(14) 0.7525(4) -0.0693(17) 0.031(3) Uani 1 1 d . . . H18 H 0.1059 0.7870 -0.0960 0.037 Uiso 1 1 calc R . . C19 C 0.0837(15) 0.7357(4) 0.1073(15) 0.030(3) Uani 1 1 d . . . H19 H 0.0883 0.7595 0.2016 0.036 Uiso 1 1 calc R . . C20 C 0.0691(13) 0.6856(4) 0.1513(13) 0.021(2) Uani 1 1 d . . . H20 H 0.0642 0.6749 0.2729 0.025 Uiso 1 1 calc R . . C21 C 0.0374(13) 0.5975(4) 0.0559(11) 0.019(2) Uani 1 1 d . . . H21 H 0.0806 0.5885 0.1800 0.023 Uiso 1 1 calc R . . C22 C -0.1162(14) 0.5648(4) -0.0213(13) 0.022(2) Uani 1 1 d . . . H22A H -0.1690 0.5377 0.0552 0.026 Uiso 1 1 calc R . . H22B H -0.2139 0.5802 -0.1031 0.026 Uiso 1 1 calc R . . C23 C 0.1622(13) 0.4650(4) -0.1727(12) 0.0161(19) Uani 1 1 d . . . C24 C 0.1261(15) 0.4164(4) -0.1030(13) 0.026(2) Uani 1 1 d . . . H24 H 0.1205 0.4104 0.0226 0.031 Uiso 1 1 calc R . . C25 C 0.0992(13) 0.3782(4) -0.2263(13) 0.022(2) Uani 1 1 d . . . H25 H 0.0742 0.3451 -0.1873 0.027 Uiso 1 1 calc R . . C26 C 0.1097(14) 0.3895(4) -0.4072(14) 0.023(2) Uani 1 1 d . . . C27 C 0.1389(13) 0.4369(4) -0.4777(14) 0.020(2) Uani 1 1 d . . . H27 H 0.1404 0.4432 -0.6032 0.023 Uiso 1 1 calc R . . C28 C 0.1660(13) 0.4747(3) -0.3506(12) 0.017(2) Uani 1 1 d . . . H28 H 0.1875 0.5079 -0.3903 0.021 Uiso 1 1 calc R . . N1 N 0.6114(11) 0.5538(3) -0.5927(10) 0.0197(18) Uani 1 1 d . . . N2 N 0.5923(12) 0.7663(3) -1.0417(12) 0.026(2) Uani 1 1 d . . . N3 N 0.0884(11) 0.5602(3) -0.0857(11) 0.0185(18) Uani 1 1 d . . . N4 N 0.0786(12) 0.3475(3) -0.5389(12) 0.025(2) Uani 1 1 d . . . O1 O 0.2836(9) 0.5900(3) -0.5285(9) 0.0225(16) Uani 1 1 d . . . O2 O 0.5595(9) 0.6199(3) -0.3393(9) 0.0243(16) Uani 1 1 d . . . O3 O 0.5936(11) 0.7573(3) -1.2036(9) 0.0289(17) Uani 1 1 d . . . O4 O 0.5946(12) 0.8109(3) -0.9839(11) 0.0357(19) Uani 1 1 d . . . O5 O 0.4218(9) 0.5251(3) -0.0321(8) 0.0220(16) Uani 1 1 d . . . O6 O 0.1490(10) 0.4959(3) 0.1625(8) 0.0227(16) Uani 1 1 d . . . O7 O 0.0775(11) 0.3597(3) -0.6993(9) 0.0311(18) Uani 1 1 d . . . O8 O 0.0629(12) 0.3067(3) -0.4816(10) 0.0333(19) Uani 1 1 d . . . S1 S 0.4910(3) 0.60299(9) -0.5101(3) 0.0180(5) Uani 1 1 d . . . S2 S 0.2188(3) 0.51176(9) -0.0118(3) 0.0165(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 C1 0.015(5) 0.027(6) 0.020(5) -0.003(4) -0.001(4) 0.002(4) C2 0.019(5) 0.022(5) 0.020(5) -0.009(4) 0.006(4) 0.002(4) C3 0.022(5) 0.032(7) 0.047(7) -0.001(6) -0.002(5) -0.008(5) C4 0.032(6) 0.023(7) 0.051(7) -0.010(6) 0.006(5) -0.011(5) C5 0.023(5) 0.016(6) 0.061(8) 0.004(6) -0.012(5) 0.010(4) C6 0.018(5) 0.029(6) 0.035(6) 0.009(5) -0.001(4) 0.002(4) C7 0.015(4) 0.026(6) 0.029(5) 0.011(5) -0.004(4) -0.002(4) C8 0.012(5) 0.021(5) 0.023(5) 0.001(4) -0.001(4) 0.002(4) C9 0.024(5) 0.015(5) 0.015(5) -0.004(4) -0.005(4) 0.002(4) C10 0.019(5) 0.019(5) 0.013(4) 0.002(4) -0.006(4) -0.005(4) C11 0.006(4) 0.026(5) 0.016(5) -0.005(4) 0.002(3) -0.001(4) C12 0.031(5) 0.013(5) 0.008(4) 0.006(4) 0.003(4) 0.000(4) C13 0.028(5) 0.022(6) 0.032(6) -0.001(5) 0.000(4) -0.011(5) C14 0.027(5) 0.027(6) 0.017(5) -0.005(4) -0.010(4) -0.005(4) C15 0.010(4) 0.023(5) 0.017(5) 0.006(4) -0.005(4) -0.003(4) C16 0.034(6) 0.032(7) 0.029(6) -0.002(5) -0.007(5) 0.003(5) C17 0.021(5) 0.027(6) 0.050(8) 0.014(6) 0.000(5) -0.007(5) C18 0.012(5) 0.028(6) 0.052(8) 0.000(6) 0.006(5) 0.011(4) C19 0.026(6) 0.031(7) 0.032(6) -0.014(5) -0.001(5) 0.006(5) C20 0.013(4) 0.028(6) 0.022(5) -0.002(4) -0.007(4) -0.006(4) C21 0.025(5) 0.024(5) 0.008(4) -0.003(4) 0.000(3) 0.003(4) C22 0.023(5) 0.026(6) 0.016(5) 0.008(4) -0.002(4) -0.003(4) C23 0.018(4) 0.020(5) 0.011(4) -0.005(4) -0.001(3) 0.000(4) C24 0.034(5) 0.028(6) 0.016(5) 0.004(5) 0.007(4) -0.004(5) C25 0.019(5) 0.028(6) 0.020(5) 0.011(5) 0.006(4) 0.002(4) C26 0.020(5) 0.027(6) 0.023(5) -0.001(5) -0.001(4) 0.005(4) C27 0.014(5) 0.024(6) 0.020(5) 0.003(4) 0.002(4) 0.000(4) C28 0.015(4) 0.013(5) 0.024(5) 0.003(4) -0.003(4) 0.003(4) N1 0.020(4) 0.026(5) 0.013(4) -0.001(4) -0.001(3) -0.004(3) N2 0.023(4) 0.025(5) 0.031(5) 0.010(4) -0.012(4) -0.003(4) N3 0.021(4) 0.012(4) 0.022(4) 0.002(3) 0.001(3) 0.002(3) N4 0.022(4) 0.023(5) 0.031(5) -0.005(4) -0.004(4) -0.006(4) O1 0.014(3) 0.023(4) 0.031(4) 0.007(3) 0.003(3) 0.006(3) O2 0.023(3) 0.029(4) 0.021(3) -0.008(3) -0.004(3) 0.000(3) O3 0.042(4) 0.034(5) 0.010(3) 0.001(3) -0.002(3) 0.003(3) O4 0.050(5) 0.022(5) 0.034(4) 0.000(4) -0.009(4) 0.007(4) O5 0.018(3) 0.031(4) 0.017(3) -0.009(3) -0.002(3) -0.004(3) O6 0.039(4) 0.020(4) 0.009(3) 0.005(3) -0.005(3) -0.002(3) O7 0.045(5) 0.031(5) 0.017(4) -0.003(3) -0.005(3) 0.006(4) O8 0.049(5) 0.019(4) 0.032(4) -0.006(4) 0.001(4) -0.001(3) S1 0.0188(11) 0.0174(11) 0.0178(11) -0.0006(10) -0.0027(8) -0.0003(10) S2 0.0174(11) 0.0190(12) 0.0130(10) 0.0010(10) 0.0019(8) 0.0017(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 C1 C6 1.386(15) . ? C1 C2 1.407(13) . ? C1 C7 1.472(15) . ? C2 C3 1.395(15) . ? C3 C4 1.367(17) . ? C4 C5 1.393(17) . ? C5 C6 1.394(16) . ? C7 C8 1.494(13) . ? C7 N1 1.516(12) . ? C8 N1 1.503(12) . ? C9 C14 1.396(13) . ? C9 C10 1.423(12) . ? C9 S1 1.758(10) . ? C10 C11 1.401(13) . ? C11 C12 1.385(13) . ? C12 C13 1.369(14) . ? C12 N2 1.469(12) . ? C13 C14 1.408(15) . ? C15 C16 1.389(14) . ? C15 C20 1.420(14) . ? C15 C21 1.482(14) . ? C16 C17 1.365(16) . ? C17 C18 1.359(17) . ? C18 C19 1.392(16) . ? C19 C20 1.385(15) . ? C21 C22 1.477(13) . ? C21 N3 1.492(12) . ? C22 N3 1.470(13) . ? C23 C28 1.350(13) . ? C23 C24 1.422(14) . ? C23 S2 1.777(9) . ? C24 C25 1.388(15) . ? C25 C26 1.383(14) . ? C26 C27 1.389(14) . ? C26 N4 1.509(13) . ? C27 C28 1.399(14) . ? N1 S1 1.666(9) . ? N2 O3 1.230(11) . ? N2 O4 1.272(12) . ? N3 S2 1.665(8) . ? N4 O8 1.177(11) . ? N4 O7 1.240(11) . ? O1 S1 1.454(7) . ? O2 S1 1.429(7) . ? O5 S2 1.428(7) . ? O6 S2 1.445(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C2 119.3(10) . . ? C6 C1 C7 118.7(9) . . ? C2 C1 C7 122.0(9) . . ? C3 C2 C1 117.9(10) . . ? C4 C3 C2 122.4(11) . . ? C3 C4 C5 120.3(11) . . ? C4 C5 C6 118.0(11) . . ? C1 C6 C5 122.2(11) . . ? C1 C7 C8 123.5(9) . . ? C1 C7 N1 116.6(8) . . ? C8 C7 N1 59.9(6) . . ? C7 C8 N1 60.8(6) . . ? C14 C9 C10 121.7(9) . . ? C14 C9 S1 118.3(7) . . ? C10 C9 S1 119.6(7) . . ? C11 C10 C9 119.1(9) . . ? C12 C11 C10 117.2(8) . . ? C13 C12 C11 125.0(9) . . ? C13 C12 N2 118.9(9) . . ? C11 C12 N2 116.0(8) . . ? C12 C13 C14 118.6(10) . . ? C9 C14 C13 118.3(9) . . ? C16 C15 C20 119.5(10) . . ? C16 C15 C21 123.4(9) . . ? C20 C15 C21 117.1(8) . . ? C17 C16 C15 120.1(11) . . ? C18 C17 C16 122.6(12) . . ? C17 C18 C19 117.6(11) . . ? C20 C19 C18 122.8(10) . . ? C19 C20 C15 117.4(9) . . ? C22 C21 C15 123.7(8) . . ? C22 C21 N3 59.4(6) . . ? C15 C21 N3 116.7(8) . . ? N3 C22 C21 60.8(6) . . ? C28 C23 C24 122.5(9) . . ? C28 C23 S2 121.5(8) . . ? C24 C23 S2 115.9(7) . . ? C25 C24 C23 117.2(9) . . ? C26 C25 C24 118.5(10) . . ? C25 C26 C27 125.1(10) . . ? C25 C26 N4 117.6(9) . . ? C27 C26 N4 117.3(9) . . ? C26 C27 C28 115.2(9) . . ? C23 C28 C27 121.5(9) . . ? C8 N1 C7 59.3(6) . . ? C8 N1 S1 113.4(6) . . ? C7 N1 S1 111.4(6) . . ? O3 N2 O4 121.1(9) . . ? O3 N2 C12 120.9(9) . . ? O4 N2 C12 118.0(9) . . ? C22 N3 C21 59.8(6) . . ? C22 N3 S2 117.3(6) . . ? C21 N3 S2 114.3(6) . . ? O8 N4 O7 126.5(9) . . ? O8 N4 C26 118.0(9) . . ? O7 N4 C26 115.4(9) . . ? O2 S1 O1 118.4(4) . . ? O2 S1 N1 114.8(4) . . ? O1 S1 N1 104.3(4) . . ? O2 S1 C9 107.4(4) . . ? O1 S1 C9 108.0(4) . . ? N1 S1 C9 102.6(4) . . ? O5 S2 O6 118.8(4) . . ? O5 S2 N3 106.3(4) . . ? O6 S2 N3 110.7(4) . . ? O5 S2 C23 108.3(4) . . ? O6 S2 C23 109.1(4) . . ? N3 S2 C23 102.3(4) . . ? _diffrn_measured_fraction_theta_max 0.937 _diffrn_reflns_theta_full 27.39 _diffrn_measured_fraction_theta_full 0.937 _refine_diff_density_max 0.865 _refine_diff_density_min -0.616 _refine_diff_density_rms 0.130 data_gjh0804 _database_code_depnum_ccdc_archive 'CCDC 791965' #TrackingRef 'gjh0804.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H12 N2 O4 S' _chemical_formula_sum 'C14 H12 N2 O4 S' _chemical_formula_weight 304.32 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/a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 13.4830(5) _cell_length_b 7.5430(3) _cell_length_c 14.7650(5) _cell_angle_alpha 90.00 _cell_angle_beta 114.997(2) _cell_angle_gamma 90.00 _cell_volume 1360.98(9) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2422 _cell_measurement_theta_min 3.02 _cell_measurement_theta_max 27.47 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.485 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 632 _exptl_absorpt_coefficient_mu 0.256 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9159 _exptl_absorpt_correction_T_max 0.9873 _exptl_absorpt_process_details Denzo/Scalepack _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'CCD scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5092 _diffrn_reflns_av_R_equivalents 0.0360 _diffrn_reflns_av_sigmaI/netI 0.0623 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.02 _diffrn_reflns_theta_max 27.47 _reflns_number_total 3105 _reflns_number_gt 2422 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'cOLLECT,Nonius BV, 1997-2001' _computing_cell_refinement DENZO/SCALEPACK _computing_data_reduction DENZO/SCALEPACK _computing_structure_solution SHELXs-97 _computing_structure_refinement SHELXL-97 _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^)+(0.0418P)^2^+0.4496P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3105 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0650 _refine_ls_R_factor_gt 0.0450 _refine_ls_wR_factor_ref 0.1090 _refine_ls_wR_factor_gt 0.0997 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _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 C1 C 0.51424(14) -0.3870(2) 0.31710(13) 0.0188(4) Uani 1 1 d . . . C2 C 0.49823(16) -0.3292(3) 0.22230(13) 0.0237(4) Uani 1 1 d . . . H2 H 0.5027 -0.2066 0.2097 0.028 Uiso 1 1 calc R . . C3 C 0.47573(16) -0.4522(3) 0.14688(14) 0.0237(4) Uani 1 1 d . . . H3 H 0.4633 -0.4159 0.0813 0.028 Uiso 1 1 calc R . . C4 C 0.47179(15) -0.6297(2) 0.16917(13) 0.0199(4) Uani 1 1 d . . . C5 C 0.49079(14) -0.6895(2) 0.26358(13) 0.0202(4) Uani 1 1 d . . . H5 H 0.4900 -0.8126 0.2768 0.024 Uiso 1 1 calc R . . C6 C 0.51096(14) -0.5654(2) 0.33839(13) 0.0195(4) Uani 1 1 d . . . H6 H 0.5224 -0.6020 0.4036 0.023 Uiso 1 1 calc R . . C7 C 0.69595(15) -0.1696(3) 0.58583(13) 0.0215(4) Uani 1 1 d . . . H7 H 0.6666 -0.0462 0.5700 0.026 Uiso 1 1 calc R . . C8 C 0.74533(16) -0.2409(3) 0.52054(14) 0.0227(4) Uani 1 1 d . . . H8A H 0.8083 -0.3227 0.5510 0.027 Uiso 1 1 calc R . . H8B H 0.7485 -0.1616 0.4684 0.027 Uiso 1 1 calc R . . C9 C 0.73162(15) -0.2246(3) 0.69133(13) 0.0214(4) Uani 1 1 d . . . C10 C 0.75697(16) -0.4002(3) 0.72155(14) 0.0266(5) Uani 1 1 d . . . H10 H 0.7493 -0.4892 0.6735 0.032 Uiso 1 1 calc R . . C11 C 0.79346(16) -0.4458(3) 0.82169(15) 0.0335(5) Uani 1 1 d . . . H11 H 0.8112 -0.5655 0.8421 0.040 Uiso 1 1 calc R . . C12 C 0.80396(17) -0.3161(3) 0.89168(15) 0.0360(6) Uani 1 1 d . . . H12 H 0.8285 -0.3475 0.9601 0.043 Uiso 1 1 calc R . . C13 C 0.77889(17) -0.1414(3) 0.86267(15) 0.0340(5) Uani 1 1 d . . . H13 H 0.7865 -0.0529 0.9109 0.041 Uiso 1 1 calc R . . C14 C 0.74254(15) -0.0960(3) 0.76242(14) 0.0275(5) Uani 1 1 d . . . H14 H 0.7250 0.0240 0.7423 0.033 Uiso 1 1 calc R . . N1 N 0.44339(13) -0.7617(2) 0.08826(12) 0.0245(4) Uani 1 1 d . . . N2 N 0.63598(12) -0.3066(2) 0.50716(11) 0.0205(4) Uani 1 1 d . . . O1 O 0.41872(13) -0.7072(2) 0.00322(10) 0.0376(4) Uani 1 1 d . . . O2 O 0.44442(12) -0.91837(19) 0.10940(10) 0.0324(4) Uani 1 1 d . . . O3 O 0.55075(11) -0.05888(18) 0.37723(9) 0.0271(3) Uani 1 1 d . . . O4 O 0.43712(11) -0.24130(18) 0.43443(9) 0.0256(3) Uani 1 1 d . . . S1 S 0.52868(4) -0.22816(6) 0.40968(3) 0.01951(14) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0167(9) 0.0188(9) 0.0203(9) 0.0017(8) 0.0072(7) 0.0010(7) C2 0.0288(10) 0.0187(9) 0.0228(10) 0.0050(8) 0.0102(8) -0.0017(8) C3 0.0284(10) 0.0236(10) 0.0181(9) 0.0053(8) 0.0090(8) 0.0007(8) C4 0.0186(9) 0.0215(10) 0.0190(9) -0.0019(8) 0.0072(7) 0.0016(8) C5 0.0174(9) 0.0182(9) 0.0236(9) 0.0036(8) 0.0073(7) 0.0004(7) C6 0.0196(9) 0.0213(10) 0.0175(9) 0.0041(8) 0.0077(7) 0.0008(8) C7 0.0217(9) 0.0186(9) 0.0228(10) -0.0006(8) 0.0080(8) -0.0022(8) C8 0.0201(9) 0.0234(10) 0.0255(10) 0.0008(8) 0.0106(8) 0.0014(8) C9 0.0165(9) 0.0261(10) 0.0205(9) -0.0001(8) 0.0067(7) -0.0002(8) C10 0.0255(10) 0.0301(11) 0.0232(10) 0.0022(9) 0.0093(8) 0.0043(9) C11 0.0252(11) 0.0416(13) 0.0310(11) 0.0123(10) 0.0091(9) 0.0054(10) C12 0.0251(11) 0.0592(16) 0.0198(10) 0.0042(11) 0.0056(8) -0.0032(11) C13 0.0255(11) 0.0512(15) 0.0226(10) -0.0097(10) 0.0073(9) -0.0111(10) C14 0.0218(10) 0.0311(11) 0.0287(10) -0.0045(9) 0.0098(8) -0.0033(9) N1 0.0240(8) 0.0265(10) 0.0210(8) -0.0022(7) 0.0075(7) 0.0002(7) N2 0.0208(8) 0.0191(8) 0.0192(8) 0.0005(7) 0.0062(6) -0.0013(7) O1 0.0535(10) 0.0357(9) 0.0194(7) -0.0002(7) 0.0114(7) -0.0004(8) O2 0.0422(9) 0.0210(8) 0.0335(8) -0.0029(6) 0.0156(7) -0.0013(7) O3 0.0352(8) 0.0168(7) 0.0243(7) 0.0039(6) 0.0079(6) -0.0001(6) O4 0.0239(7) 0.0288(8) 0.0244(7) 0.0006(6) 0.0106(6) 0.0039(6) S1 0.0215(2) 0.0169(2) 0.0183(2) 0.00206(19) 0.00665(19) 0.00108(19) _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 C1 C6 1.387(3) . ? C1 C2 1.393(3) . ? C1 S1 1.7656(19) . ? C2 C3 1.381(3) . ? C2 H2 0.9500 . ? C3 C4 1.385(3) . ? C3 H3 0.9500 . ? C4 C5 1.382(3) . ? C4 N1 1.476(2) . ? C5 C6 1.384(3) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C9 1.482(3) . ? C7 C8 1.485(3) . ? C7 N2 1.509(2) . ? C7 H7 1.0000 . ? C8 N2 1.487(2) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C14 1.391(3) . ? C9 C10 1.393(3) . ? C10 C11 1.390(3) . ? C10 H10 0.9500 . ? C11 C12 1.386(3) . ? C11 H11 0.9500 . ? C12 C13 1.383(3) . ? C12 H12 0.9500 . ? C13 C14 1.391(3) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? N1 O2 1.221(2) . ? N1 O1 1.226(2) . ? N2 S1 1.6598(15) . ? O3 S1 1.4384(14) . ? O4 S1 1.4314(14) . ? 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 C6 C1 C2 121.70(18) . . ? C6 C1 S1 119.11(14) . . ? C2 C1 S1 119.01(14) . . ? C3 C2 C1 119.19(18) . . ? C3 C2 H2 120.4 . . ? C1 C2 H2 120.4 . . ? C2 C3 C4 118.38(17) . . ? C2 C3 H3 120.8 . . ? C4 C3 H3 120.8 . . ? C5 C4 C3 123.06(17) . . ? C5 C4 N1 118.06(16) . . ? C3 C4 N1 118.86(16) . . ? C4 C5 C6 118.33(17) . . ? C4 C5 H5 120.8 . . ? C6 C5 H5 120.8 . . ? C5 C6 C1 119.30(17) . . ? C5 C6 H6 120.3 . . ? C1 C6 H6 120.3 . . ? C9 C7 C8 123.06(17) . . ? C9 C7 N2 116.59(16) . . ? C8 C7 N2 59.57(12) . . ? C9 C7 H7 115.3 . . ? C8 C7 H7 115.3 . . ? N2 C7 H7 115.3 . . ? C7 C8 N2 61.03(12) . . ? C7 C8 H8A 117.7 . . ? N2 C8 H8A 117.7 . . ? C7 C8 H8B 117.7 . . ? N2 C8 H8B 117.7 . . ? H8A C8 H8B 114.8 . . ? C14 C9 C10 119.22(18) . . ? C14 C9 C7 118.79(18) . . ? C10 C9 C7 121.97(17) . . ? C11 C10 C9 120.3(2) . . ? C11 C10 H10 119.8 . . ? C9 C10 H10 119.8 . . ? C12 C11 C10 119.8(2) . . ? C12 C11 H11 120.1 . . ? C10 C11 H11 120.1 . . ? C13 C12 C11 120.46(19) . . ? C13 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? C12 C13 C14 119.6(2) . . ? C12 C13 H13 120.2 . . ? C14 C13 H13 120.2 . . ? C9 C14 C13 120.5(2) . . ? C9 C14 H14 119.7 . . ? C13 C14 H14 119.7 . . ? O2 N1 O1 123.74(17) . . ? O2 N1 C4 118.36(15) . . ? O1 N1 C4 117.90(16) . . ? C8 N2 C7 59.40(12) . . ? C8 N2 S1 116.63(12) . . ? C7 N2 S1 114.23(12) . . ? O4 S1 O3 117.95(8) . . ? O4 S1 N2 106.48(8) . . ? O3 S1 N2 112.22(8) . . ? O4 S1 C1 109.02(8) . . ? O3 S1 C1 108.37(8) . . ? N2 S1 C1 101.53(8) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.287 _refine_diff_density_min -0.372 _refine_diff_density_rms 0.062