# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Andrew White' _publ_contact_author_email a.white@imperial.ac.uk loop_ _publ_author_name C.Kontogiorgis A.Miller T.Rost R.Berge J.Skorve Y.Bhurruth-Alcor M.Jorgensen W.Hamilton data_Compound_25 _database_code_depnum_ccdc_archive 'CCDC 667594' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H16 N2 O2 S' _chemical_formula_sum 'C22 H16 N2 O2 S' _chemical_formula_weight 372.43 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 P2(1)/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 10.8591(3) _cell_length_b 10.0425(3) _cell_length_c 17.0542(4) _cell_angle_alpha 90.00 _cell_angle_beta 100.888(3) _cell_angle_gamma 90.00 _cell_volume 1826.32(9) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4785 _cell_measurement_theta_min 3.7750 _cell_measurement_theta_max 28.8460 _exptl_crystal_description blocks _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.11 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.354 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 776 _exptl_absorpt_coefficient_mu 0.197 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.976 _exptl_absorpt_correction_T_max 0.988 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'OD Xcalibur 3' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean 15.9863 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12993 _diffrn_reflns_av_R_equivalents 0.0606 _diffrn_reflns_av_sigmaI/netI 0.0621 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.79 _diffrn_reflns_theta_max 28.96 _reflns_number_total 4231 _reflns_number_gt 2710 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd' _computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd' _computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0542P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4231 _refine_ls_number_parameters 245 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.0808 _refine_ls_R_factor_gt 0.0438 _refine_ls_wR_factor_ref 0.1155 _refine_ls_wR_factor_gt 0.1012 _refine_ls_goodness_of_fit_ref 1.040 _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 N1 N 0.58850(12) 0.94935(14) 0.89361(8) 0.0372(3) Uani 1 1 d . A . C2 C 0.69146(15) 0.9818(2) 0.95585(10) 0.0409(4) Uani 1 1 d . . . C3 C 0.66789(15) 1.0993(2) 0.98703(10) 0.0451(5) Uani 1 1 d . . . H3A H 0.7210 1.1425 1.0302 0.054 Uiso 1 1 calc R . . C4 C 0.55142(15) 1.14953(19) 0.94562(10) 0.0398(4) Uani 1 1 d . . . C5 C 0.48547(17) 1.2660(2) 0.95259(11) 0.0454(5) Uani 1 1 d . . . H5A H 0.5168 1.3297 0.9926 0.054 Uiso 1 1 calc R . . C6 C 0.37405(18) 1.28779(19) 0.90068(11) 0.0456(5) Uani 1 1 d . . . C7 C 0.32607(16) 1.1936(2) 0.84183(11) 0.0438(4) Uani 1 1 d . . . H7A H 0.2488 1.2108 0.8067 0.053 Uiso 1 1 calc R . . C8 C 0.38902(15) 1.0772(2) 0.83434(10) 0.0419(4) Uani 1 1 d . . . H8A H 0.3564 1.0134 0.7947 0.050 Uiso 1 1 calc R . . C9 C 0.50191(15) 1.05544(18) 0.88659(9) 0.0363(4) Uani 1 1 d . . . S10 S 0.56610(4) 0.80969(5) 0.83901(3) 0.04155(16) Uani 1 1 d D . . O11 O 0.64141(13) 0.70998(14) 0.88334(8) 0.0609(4) Uani 1 1 d . A . O12 O 0.43393(11) 0.79307(13) 0.81821(8) 0.0532(4) Uani 1 1 d . A . C13 C 0.6292(3) 0.8375(3) 0.75531(15) 0.0417(11) Uani 0.702(10) 1 d PGD A 1 C14 C 0.5651(5) 0.9162(4) 0.69387(19) 0.0688(14) Uani 0.702(10) 1 d PGD A 1 H14A H 0.4858 0.9530 0.6977 0.083 Uiso 0.702(10) 1 calc PR A 1 C15 C 0.6168(7) 0.9410(3) 0.6267(2) 0.090(2) Uani 0.702(10) 1 d PG A 1 H15A H 0.5730 0.9948 0.5847 0.108 Uiso 0.702(10) 1 calc PR A 1 C16 C 0.7327(6) 0.8872(3) 0.6211(2) 0.0712(17) Uani 0.702(10) 1 d PG A 1 H16A H 0.7681 0.9041 0.5752 0.085 Uiso 0.702(10) 1 calc PR A 1 C17 C 0.7969(3) 0.8085(5) 0.6825(2) 0.0609(15) Uani 0.702(10) 1 d PG A 1 H17A H 0.8761 0.7716 0.6786 0.073 Uiso 0.702(10) 1 calc PR A 1 C18 C 0.7451(2) 0.7836(5) 0.74963(14) 0.0498(11) Uani 0.702(10) 1 d PGD A 1 H18A H 0.7889 0.7298 0.7916 0.060 Uiso 0.702(10) 1 calc PR A 1 C13' C 0.6106(5) 0.8552(9) 0.7478(3) 0.030(2) Uiso 0.298(10) 1 d PGD A 2 C14' C 0.5194(5) 0.9033(8) 0.6859(4) 0.041(2) Uiso 0.298(10) 1 d PGD A 2 H14B H 0.4359 0.9157 0.6939 0.049 Uiso 0.298(10) 1 calc PR A 2 C15' C 0.5505(6) 0.9333(7) 0.6125(3) 0.049(2) Uiso 0.298(10) 1 d PG A 2 H15B H 0.4882 0.9663 0.5702 0.058 Uiso 0.298(10) 1 calc PR A 2 C16' C 0.6727(6) 0.9152(7) 0.6009(3) 0.044(2) Uiso 0.298(10) 1 d PG A 2 H16B H 0.6939 0.9357 0.5507 0.053 Uiso 0.298(10) 1 calc PR A 2 C17' C 0.7638(5) 0.8670(8) 0.6628(3) 0.035(2) Uiso 0.298(10) 1 d PG A 2 H17B H 0.8474 0.8546 0.6549 0.042 Uiso 0.298(10) 1 calc PR A 2 C18' C 0.7328(5) 0.8370(8) 0.7362(3) 0.045(2) Uiso 0.298(10) 1 d PGD A 2 H18B H 0.7951 0.8041 0.7785 0.054 Uiso 0.298(10) 1 calc PR A 2 C19 C 0.80761(16) 0.8994(2) 0.97983(10) 0.0490(5) Uani 1 1 d . . . H19A H 0.7822 0.8060 0.9864 0.059 Uiso 1 1 calc R . . H19B H 0.8525 0.9310 1.0325 0.059 Uiso 1 1 calc R . . C20 C 0.89827(15) 0.90162(18) 0.92215(10) 0.0381(4) Uani 1 1 d . . . C21 C 0.90877(16) 1.01031(18) 0.87401(11) 0.0417(4) Uani 1 1 d . . . H21A H 0.8576 1.0863 0.8764 0.050 Uiso 1 1 calc R . . C22 C 0.99268(16) 1.00966(19) 0.82253(11) 0.0447(5) Uani 1 1 d . . . H22A H 0.9986 1.0849 0.7897 0.054 Uiso 1 1 calc R . . C23 C 1.06792(16) 0.9005(2) 0.81846(11) 0.0473(5) Uani 1 1 d . . . H23A H 1.1249 0.9000 0.7825 0.057 Uiso 1 1 calc R . . C24 C 1.06037(17) 0.7934(2) 0.86628(13) 0.0509(5) Uani 1 1 d . . . H24A H 1.1125 0.7181 0.8638 0.061 Uiso 1 1 calc R . . C25 C 0.97669(17) 0.79392(19) 0.91863(12) 0.0475(5) Uani 1 1 d . . . H25A H 0.9732 0.7194 0.9525 0.057 Uiso 1 1 calc R . . C26 C 0.3051(2) 1.4086(2) 0.90767(13) 0.0599(6) Uani 1 1 d . . . N26 N 0.2505(2) 1.5037(2) 0.91303(15) 0.0878(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 N1 0.0333(7) 0.0466(9) 0.0319(7) -0.0052(7) 0.0070(6) 0.0009(7) C2 0.0325(8) 0.0623(13) 0.0288(8) 0.0001(9) 0.0080(7) -0.0023(9) C3 0.0359(9) 0.0677(14) 0.0319(9) -0.0126(9) 0.0069(8) -0.0088(9) C4 0.0363(9) 0.0531(12) 0.0322(9) -0.0070(8) 0.0120(8) -0.0069(8) C5 0.0496(11) 0.0496(13) 0.0415(10) -0.0099(9) 0.0205(9) -0.0085(10) C6 0.0469(10) 0.0460(12) 0.0489(11) 0.0026(9) 0.0221(9) 0.0010(9) C7 0.0347(9) 0.0544(12) 0.0436(10) 0.0020(10) 0.0106(8) 0.0024(9) C8 0.0356(9) 0.0537(12) 0.0366(9) -0.0070(9) 0.0071(8) -0.0038(9) C9 0.0340(8) 0.0463(11) 0.0309(8) -0.0020(8) 0.0121(7) -0.0026(8) S10 0.0442(3) 0.0445(3) 0.0380(2) -0.0024(2) 0.0130(2) -0.0023(2) O11 0.0802(10) 0.0514(9) 0.0510(8) 0.0067(7) 0.0121(8) 0.0175(8) O12 0.0446(7) 0.0561(9) 0.0612(8) -0.0128(7) 0.0161(6) -0.0131(6) C13 0.0479(19) 0.038(2) 0.0407(16) -0.0106(13) 0.0110(14) -0.0021(14) C14 0.096(3) 0.066(3) 0.052(2) 0.0055(18) 0.033(2) 0.035(3) C15 0.167(6) 0.056(2) 0.063(2) 0.0203(19) 0.059(3) 0.045(3) C16 0.113(5) 0.057(2) 0.057(2) -0.008(2) 0.049(3) -0.012(3) C17 0.0534(19) 0.085(3) 0.0495(19) -0.028(2) 0.0233(17) -0.015(2) C18 0.0428(16) 0.071(3) 0.0354(15) -0.0197(16) 0.0073(12) -0.0023(16) C19 0.0409(10) 0.0704(14) 0.0355(9) 0.0089(10) 0.0066(8) 0.0030(10) C20 0.0321(8) 0.0430(11) 0.0371(9) 0.0015(8) 0.0010(7) 0.0019(8) C21 0.0418(9) 0.0375(11) 0.0471(10) 0.0006(9) 0.0116(8) 0.0082(8) C22 0.0465(10) 0.0408(11) 0.0495(11) 0.0015(9) 0.0162(9) 0.0017(9) C23 0.0370(9) 0.0562(13) 0.0498(11) -0.0105(10) 0.0108(8) -0.0003(9) C24 0.0399(10) 0.0425(12) 0.0673(13) -0.0132(11) 0.0022(9) 0.0099(9) C25 0.0463(10) 0.0411(11) 0.0515(11) 0.0056(9) -0.0002(9) 0.0039(9) C26 0.0648(13) 0.0556(14) 0.0639(14) 0.0005(12) 0.0235(11) 0.0065(12) N26 0.1008(15) 0.0637(14) 0.1022(18) 0.0002(12) 0.0279(14) 0.0277(13) _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 N1 C9 1.411(2) . ? N1 C2 1.426(2) . ? N1 S10 1.6757(14) . ? C2 C3 1.339(3) . ? C2 C19 1.499(2) . ? C3 C4 1.419(2) . ? C4 C5 1.388(3) . ? C4 C9 1.411(2) . ? C5 C6 1.375(3) . ? C6 C7 1.406(3) . ? C6 C26 1.442(3) . ? C7 C8 1.372(2) . ? C8 C9 1.390(2) . ? S10 O11 1.4175(14) . ? S10 O12 1.4217(13) . ? S10 C13 1.7187(15) . ? S10 C13' 1.774(4) . ? C13 C14 1.3900 . ? C13 C18 1.3900 . ? C14 C15 1.3900 . ? C15 C16 1.3900 . ? C16 C17 1.3900 . ? C17 C18 1.3900 . ? C13' C14' 1.3900 . ? C13' C18' 1.3900 . ? C14' C15' 1.3900 . ? C15' C16' 1.3900 . ? C16' C17' 1.3900 . ? C17' C18' 1.3900 . ? C19 C20 1.518(2) . ? C20 C21 1.383(2) . ? C20 C25 1.385(2) . ? C21 C22 1.380(2) . ? C22 C23 1.376(3) . ? C23 C24 1.362(3) . ? C24 C25 1.389(3) . ? C26 N26 1.137(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 C9 N1 C2 107.88(14) . . ? C9 N1 S10 124.08(11) . . ? C2 N1 S10 128.00(12) . . ? C3 C2 N1 108.35(15) . . ? C3 C2 C19 126.30(16) . . ? N1 C2 C19 125.32(16) . . ? C2 C3 C4 109.55(16) . . ? C5 C4 C9 119.48(16) . . ? C5 C4 C3 133.01(17) . . ? C9 C4 C3 107.50(16) . . ? C6 C5 C4 118.96(17) . . ? C5 C6 C7 121.00(18) . . ? C5 C6 C26 119.20(19) . . ? C7 C6 C26 119.79(18) . . ? C8 C7 C6 121.05(17) . . ? C7 C8 C9 117.94(17) . . ? C8 C9 C4 121.56(17) . . ? C8 C9 N1 131.74(16) . . ? C4 C9 N1 106.68(15) . . ? O11 S10 O12 120.25(9) . . ? O11 S10 N1 106.64(8) . . ? O12 S10 N1 105.70(7) . . ? O11 S10 C13 106.10(13) . . ? O12 S10 C13 110.72(13) . . ? N1 S10 C13 106.66(12) . . ? O11 S10 C13' 115.1(2) . . ? O12 S10 C13' 103.9(2) . . ? N1 S10 C13' 103.7(3) . . ? C13 S10 C13' 9.0(2) . . ? C14 C13 C18 120.0 . . ? C14 C13 S10 119.80(13) . . ? C18 C13 S10 120.19(13) . . ? C15 C14 C13 120.0 . . ? C14 C15 C16 120.0 . . ? C17 C16 C15 120.0 . . ? C16 C17 C18 120.0 . . ? C17 C18 C13 120.0 . . ? C14' C13' C18' 120.0 . . ? C14' C13' S10 118.8(3) . . ? C18' C13' S10 121.1(3) . . ? C13' C14' C15' 120.0 . . ? C16' C15' C14' 120.0 . . ? C17' C16' C15' 120.0 . . ? C18' C17' C16' 120.0 . . ? C17' C18' C13' 120.0 . . ? C2 C19 C20 115.51(14) . . ? C21 C20 C25 118.04(16) . . ? C21 C20 C19 122.17(16) . . ? C25 C20 C19 119.76(16) . . ? C22 C21 C20 120.82(17) . . ? C23 C22 C21 120.37(18) . . ? C24 C23 C22 119.70(17) . . ? C23 C24 C25 120.15(17) . . ? C20 C25 C24 120.89(18) . . ? N26 C26 C6 179.8(3) . . ? _diffrn_measured_fraction_theta_max 0.875 _diffrn_reflns_theta_full 28.96 _diffrn_measured_fraction_theta_full 0.875 _refine_diff_density_max 0.248 _refine_diff_density_min -0.307 _refine_diff_density_rms 0.039 #===END data_Compound_26 _database_code_depnum_ccdc_archive 'CCDC 667595' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H18 N2 O2 S' _chemical_formula_sum 'C26 H18 N2 O2 S' _chemical_formula_weight 422.48 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/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 18.0309(4) _cell_length_b 5.88641(15) _cell_length_c 19.5220(4) _cell_angle_alpha 90 _cell_angle_beta 98.636(2) _cell_angle_gamma 90 _cell_volume 2048.52(19) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2928 _cell_measurement_theta_min 2.2892 _cell_measurement_theta_max 62.8170 _exptl_crystal_description needles _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.370 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 880 _exptl_absorpt_coefficient_mu 1.615 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.81707 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 1.54248 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Enhance Ultra (Cu) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'OD Xcalibur PX Ultra' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean 8.2556 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8932 _diffrn_reflns_av_R_equivalents 0.0501 _diffrn_reflns_av_sigmaI/netI 0.0851 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.11 _diffrn_reflns_theta_max 63.12 _reflns_number_total 3230 _reflns_number_gt 1894 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd' _computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd' _computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0447P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3230 _refine_ls_number_parameters 280 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0879 _refine_ls_R_factor_gt 0.0404 _refine_ls_wR_factor_ref 0.0869 _refine_ls_wR_factor_gt 0.0764 _refine_ls_goodness_of_fit_ref 0.867 _refine_ls_restrained_S_all 0.867 _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 N1 N 0.44400(10) 0.1958(3) 0.31612(9) 0.0363(5) Uani 1 1 d . . . C2 C 0.52282(13) 0.1834(4) 0.34131(12) 0.0373(6) Uani 1 1 d . . . C3 C 0.54009(12) 0.3540(4) 0.38656(12) 0.0383(7) Uani 1 1 d . . . H3A H 0.5886 0.3828 0.4114 0.046 Uiso 1 1 calc R . . C4 C 0.47437(12) 0.4862(4) 0.39178(12) 0.0350(6) Uani 1 1 d . . . C5 C 0.46096(13) 0.6747(4) 0.43108(12) 0.0415(7) Uani 1 1 d . . . H5A H 0.5007 0.7458 0.4610 0.050 Uiso 1 1 calc R . . C6 C 0.38807(14) 0.7562(5) 0.42547(12) 0.0419(7) Uani 1 1 d . . . C7 C 0.32945(14) 0.6495(5) 0.38240(13) 0.0478(7) Uani 1 1 d . . . H7A H 0.2800 0.7075 0.3802 0.057 Uiso 1 1 calc R . . C8 C 0.34130(13) 0.4626(5) 0.34297(12) 0.0444(7) Uani 1 1 d . . . H8A H 0.3013 0.3908 0.3136 0.053 Uiso 1 1 calc R . . C9 C 0.41467(12) 0.3843(4) 0.34820(11) 0.0355(6) Uani 1 1 d . . . S10 S 0.39928(3) 0.07768(13) 0.24368(3) 0.0460(2) Uani 1 1 d . . . O11 O 0.44218(9) -0.1169(3) 0.23070(9) 0.0548(5) Uani 1 1 d . . . O12 O 0.32266(8) 0.0561(3) 0.25401(9) 0.0527(5) Uani 1 1 d . . . C13 C 0.40308(14) 0.2824(5) 0.17839(12) 0.0464(7) Uani 1 1 d . . . C14 C 0.34653(16) 0.4446(5) 0.16502(14) 0.0518(7) Uani 1 1 d . . . H14A H 0.3065 0.4476 0.1916 0.062 Uiso 1 1 calc R . . C15 C 0.34923(17) 0.6010(5) 0.11276(15) 0.0643(9) Uani 1 1 d . . . H15A H 0.3109 0.7122 0.1032 0.077 Uiso 1 1 calc R . . C16 C 0.4071(2) 0.5964(6) 0.07456(16) 0.0781(11) Uani 1 1 d . . . H16A H 0.4083 0.7039 0.0384 0.094 Uiso 1 1 calc R . . C17 C 0.46310(18) 0.4390(7) 0.08786(16) 0.0866(12) Uani 1 1 d . . . H17A H 0.5032 0.4388 0.0613 0.104 Uiso 1 1 calc R . . C18 C 0.46168(15) 0.2776(6) 0.14051(15) 0.0722(10) Uani 1 1 d . . . H18A H 0.5003 0.1672 0.1499 0.087 Uiso 1 1 calc R . . C19 C 0.57417(13) -0.0025(4) 0.32385(12) 0.0408(7) Uani 1 1 d . . . H19A H 0.5446 -0.1438 0.3146 0.049 Uiso 1 1 calc R . . H19B H 0.6127 -0.0303 0.3647 0.049 Uiso 1 1 calc R . . C20 C 0.61373(11) 0.0468(4) 0.26156(12) 0.0342(6) Uani 1 1 d . . . C21 C 0.61402(12) -0.1068(4) 0.20950(12) 0.0380(6) Uani 1 1 d . . . H21A H 0.5868 -0.2445 0.2107 0.046 Uiso 1 1 calc R . . C22 C 0.65421(12) -0.0658(4) 0.15322(12) 0.0351(6) Uani 1 1 d . . . C23 C 0.65610(13) -0.2247(5) 0.09937(13) 0.0473(7) Uani 1 1 d . . . H23A H 0.6285 -0.3622 0.0992 0.057 Uiso 1 1 calc R . . C24 C 0.69747(14) -0.1827(5) 0.04725(13) 0.0507(7) Uani 1 1 d . . . H24A H 0.6984 -0.2914 0.0114 0.061 Uiso 1 1 calc R . . C25 C 0.73833(14) 0.0187(5) 0.04642(14) 0.0465(7) Uani 1 1 d . . . H25A H 0.7674 0.0451 0.0105 0.056 Uiso 1 1 calc R . . C26 C 0.73657(12) 0.1772(4) 0.09697(13) 0.0408(7) Uani 1 1 d . . . H26A H 0.7636 0.3151 0.0953 0.049 Uiso 1 1 calc R . . C27 C 0.69480(12) 0.1391(4) 0.15221(12) 0.0334(6) Uani 1 1 d . . . C28 C 0.69368(12) 0.2951(4) 0.20680(12) 0.0398(6) Uani 1 1 d . . . H28A H 0.7210 0.4331 0.2067 0.048 Uiso 1 1 calc R . . C29 C 0.65411(12) 0.2521(4) 0.26007(12) 0.0385(6) Uani 1 1 d . . . H29A H 0.6538 0.3606 0.2961 0.046 Uiso 1 1 calc R . . C30 C 0.37270(14) 0.9521(5) 0.46473(14) 0.0482(7) Uani 1 1 d . . . N30 N 0.36068(12) 1.1095(4) 0.49642(12) 0.0628(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 N1 0.0292(11) 0.0430(13) 0.0359(12) -0.0002(11) 0.0026(9) -0.0036(10) C2 0.0367(14) 0.0436(17) 0.0329(14) 0.0039(14) 0.0093(12) -0.0009(13) C3 0.0285(13) 0.0497(18) 0.0368(15) 0.0020(14) 0.0052(11) 0.0031(13) C4 0.0330(14) 0.0422(17) 0.0307(14) 0.0034(13) 0.0076(12) -0.0046(12) C5 0.0421(15) 0.0484(18) 0.0341(15) 0.0017(14) 0.0065(12) -0.0013(14) C6 0.0453(16) 0.0464(18) 0.0365(16) 0.0065(14) 0.0142(13) 0.0111(14) C7 0.0390(16) 0.064(2) 0.0417(17) 0.0109(16) 0.0105(13) 0.0107(15) C8 0.0338(15) 0.061(2) 0.0392(15) 0.0028(15) 0.0063(12) 0.0001(14) C9 0.0333(14) 0.0412(17) 0.0337(14) 0.0062(13) 0.0105(12) 0.0017(13) S10 0.0397(4) 0.0505(5) 0.0472(4) -0.0024(4) 0.0044(3) -0.0125(4) O11 0.0507(11) 0.0450(12) 0.0685(13) -0.0156(10) 0.0081(9) -0.0059(10) O12 0.0361(10) 0.0598(13) 0.0615(12) 0.0007(10) 0.0052(9) -0.0171(9) C13 0.0416(15) 0.063(2) 0.0326(15) -0.0025(15) 0.0004(13) -0.0206(16) C14 0.0631(19) 0.0505(19) 0.0404(17) -0.0053(16) 0.0030(14) -0.0150(17) C15 0.085(2) 0.056(2) 0.0482(18) -0.0029(18) -0.0029(17) -0.0180(19) C16 0.074(2) 0.100(3) 0.055(2) 0.017(2) -0.0103(19) -0.039(2) C17 0.052(2) 0.157(4) 0.048(2) 0.029(2) 0.0011(16) -0.031(2) C18 0.0427(18) 0.120(3) 0.0520(19) 0.016(2) 0.0013(15) -0.0082(18) C19 0.0405(14) 0.0415(17) 0.0409(15) 0.0011(13) 0.0076(12) 0.0064(13) C20 0.0284(13) 0.0364(16) 0.0379(15) 0.0028(14) 0.0055(11) 0.0027(12) C21 0.0364(14) 0.0311(15) 0.0472(16) 0.0009(14) 0.0082(12) -0.0014(12) C22 0.0356(14) 0.0333(16) 0.0364(15) -0.0007(13) 0.0054(11) 0.0012(13) C23 0.0490(16) 0.0402(17) 0.0548(18) -0.0070(15) 0.0144(14) -0.0100(14) C24 0.0611(18) 0.0505(19) 0.0433(17) -0.0136(15) 0.0169(14) -0.0074(16) C25 0.0474(16) 0.0504(19) 0.0446(17) -0.0014(15) 0.0169(13) -0.0032(14) C26 0.0411(15) 0.0355(16) 0.0469(17) 0.0037(14) 0.0106(13) -0.0035(13) C27 0.0314(13) 0.0296(15) 0.0395(15) 0.0004(13) 0.0066(12) -0.0006(12) C28 0.0374(14) 0.0327(16) 0.0496(17) -0.0006(14) 0.0083(13) -0.0037(13) C29 0.0384(14) 0.0348(16) 0.0432(16) -0.0059(13) 0.0089(12) -0.0002(13) C30 0.0485(16) 0.054(2) 0.0441(17) 0.0101(17) 0.0142(13) 0.0137(16) N30 0.0666(16) 0.0646(19) 0.0599(17) -0.0002(15) 0.0187(13) 0.0188(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 N1 C9 1.415(3) . ? N1 C2 1.434(3) . ? N1 S10 1.6708(19) . ? C2 C3 1.343(3) . ? C2 C19 1.505(3) . ? C3 C4 1.434(3) . ? C4 C5 1.391(3) . ? C4 C9 1.403(3) . ? C5 C6 1.388(3) . ? C6 C7 1.397(3) . ? C6 C30 1.434(4) . ? C7 C8 1.377(3) . ? C8 C9 1.390(3) . ? S10 O11 1.4261(18) . ? S10 O12 1.4314(15) . ? S10 C13 1.763(3) . ? C13 C18 1.378(3) . ? C13 C14 1.393(4) . ? C14 C15 1.381(4) . ? C15 C16 1.371(4) . ? C16 C17 1.366(4) . ? C17 C18 1.403(4) . ? C19 C20 1.527(3) . ? C20 C21 1.361(3) . ? C20 C29 1.414(3) . ? C21 C22 1.425(3) . ? C22 C23 1.412(3) . ? C22 C27 1.412(3) . ? C23 C24 1.372(3) . ? C24 C25 1.397(3) . ? C25 C26 1.362(3) . ? C26 C27 1.423(3) . ? C27 C28 1.409(3) . ? C28 C29 1.370(3) . ? C30 N30 1.153(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 C9 N1 C2 107.78(19) . . ? C9 N1 S10 122.41(15) . . ? C2 N1 S10 126.61(16) . . ? C3 C2 N1 107.9(2) . . ? C3 C2 C19 127.1(2) . . ? N1 C2 C19 124.8(2) . . ? C2 C3 C4 109.9(2) . . ? C5 C4 C9 119.7(2) . . ? C5 C4 C3 133.3(2) . . ? C9 C4 C3 107.0(2) . . ? C6 C5 C4 118.3(2) . . ? C5 C6 C7 120.9(3) . . ? C5 C6 C30 119.5(2) . . ? C7 C6 C30 119.6(2) . . ? C8 C7 C6 121.9(2) . . ? C7 C8 C9 116.7(2) . . ? C8 C9 C4 122.5(2) . . ? C8 C9 N1 130.0(2) . . ? C4 C9 N1 107.45(19) . . ? O11 S10 O12 120.96(11) . . ? O11 S10 N1 106.20(10) . . ? O12 S10 N1 105.73(10) . . ? O11 S10 C13 109.86(13) . . ? O12 S10 C13 107.80(12) . . ? N1 S10 C13 105.14(11) . . ? C18 C13 C14 120.8(3) . . ? C18 C13 S10 119.3(3) . . ? C14 C13 S10 119.8(2) . . ? C15 C14 C13 119.3(3) . . ? C16 C15 C14 120.2(3) . . ? C17 C16 C15 120.7(3) . . ? C16 C17 C18 120.3(3) . . ? C13 C18 C17 118.6(3) . . ? C2 C19 C20 114.8(2) . . ? C21 C20 C29 119.5(2) . . ? C21 C20 C19 121.5(2) . . ? C29 C20 C19 118.9(2) . . ? C20 C21 C22 121.5(2) . . ? C23 C22 C27 119.0(2) . . ? C23 C22 C21 122.3(2) . . ? C27 C22 C21 118.7(2) . . ? C24 C23 C22 120.6(2) . . ? C23 C24 C25 120.6(3) . . ? C26 C25 C24 120.2(2) . . ? C25 C26 C27 120.9(2) . . ? C28 C27 C22 118.7(2) . . ? C28 C27 C26 122.7(2) . . ? C22 C27 C26 118.6(2) . . ? C29 C28 C27 121.5(2) . . ? C28 C29 C20 120.1(2) . . ? N30 C30 C6 179.7(3) . . ? _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 63.12 _diffrn_measured_fraction_theta_full 0.973 _refine_diff_density_max 0.152 _refine_diff_density_min -0.256 _refine_diff_density_rms 0.040 #===END