# Supplementary Material (ESI) for New Journal of Chemistry # This journal is (c) The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2008 data_global _journal_coden_Cambridge 440 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'Paola Paoli' 'Maria Altamura' 'Paolo Dapporto' 'Antonio Guidi' 'Nicholas J. S. Harmat' 'Loic Jierry' 'Elisa Libralesso' 'Patrizia Rossi' _publ_contact_author_name 'Paola Paoli' _publ_contact_author_email PAOLAPAOLI@UNIFI.IT _publ_section_title ; Investigation on the flexibility of tricyclic derivatives: control of the emergence of chirality ; # Attachment '1-2-3.cif' data_1 _database_code_depnum_ccdc_archive 'CCDC 685693' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H11 N O4' _chemical_formula_weight 269.25 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.5530(10) _cell_length_b 8.305(2) _cell_length_c 10.514(2) _cell_angle_alpha 68.89(2) _cell_angle_beta 80.780(10) _cell_angle_gamma 75.12(2) _cell_volume 592.9(2) _cell_formula_units_Z 2 _cell_measurement_temperature 150 _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.508 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 280 _exptl_absorpt_coefficient_mu 0.111 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.29.2 (release 20-01-2006 CrysAlis171 .NET) (compiled Jan 20 2006,12:36:28) ; _diffrn_ambient_temperature 150 _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur3 4 circles diffractometer' _diffrn_measurement_method 'intensity from \w scans' _diffrn_detector_area_resol_mean 16.4547 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6833 _diffrn_reflns_av_R_equivalents 0.0303 _diffrn_reflns_av_sigmaI/netI 0.0680 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 4.17 _diffrn_reflns_theta_max 28.50 _reflns_number_total 2599 _reflns_number_gt 1500 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.29.2 (release 20-01-2006 CrysAlis171 .NET) (compiled Jan 20 2006,12:36:28) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.29.2 (release 20-01-2006 CrysAlis171 .NET) (compiled Jan 20 2006,12:36:28) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.29.2 (release 20-01-2006 CrysAlis171 .NET) (compiled Jan 20 2006,12:36:28) ; _computing_structure_solution 'SIR97 (Altomare, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farruggia, 1997)' _computing_publication_material 'PARST97 (Nardelli, 1995)' _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^)+(0.0469P)^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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2599 _refine_ls_number_parameters 225 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0737 _refine_ls_R_factor_gt 0.0416 _refine_ls_wR_factor_ref 0.0943 _refine_ls_wR_factor_gt 0.0848 _refine_ls_goodness_of_fit_ref 0.895 _refine_ls_restrained_S_all 0.895 _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 O1 O 0.06334(16) 0.68828(14) 0.50950(12) 0.0270(3) Uani 1 1 d . . . O2 O -0.13853(17) 1.08719(17) 0.38141(12) 0.0308(3) Uani 1 1 d . . . O3 O -0.31293(18) 0.99982(17) 0.57749(13) 0.0363(3) Uani 1 1 d . . . O4 O 0.03472(16) 0.54205(14) 0.18401(11) 0.0263(3) Uani 1 1 d . . . N1 N -0.11307(18) 0.77832(17) 0.33317(13) 0.0226(3) Uani 1 1 d . . . C1 C 0.2135(2) 0.6239(2) 0.31329(16) 0.0217(4) Uani 1 1 d . . . C2 C 0.2033(2) 0.5416(2) 0.22086(17) 0.0238(4) Uani 1 1 d . . . C3 C 0.3610(3) 0.4528(2) 0.16681(18) 0.0275(4) Uani 1 1 d . . . C4 C 0.5306(3) 0.4473(2) 0.20359(19) 0.0302(5) Uani 1 1 d . . . C5 C 0.5450(3) 0.5315(2) 0.29237(18) 0.0278(4) Uani 1 1 d . . . C6 C 0.3870(2) 0.6173(2) 0.34754(18) 0.0247(4) Uani 1 1 d . . . C7 C 0.0508(2) 0.7005(2) 0.39001(17) 0.0222(4) Uani 1 1 d . . . C8 C -0.1419(2) 0.8261(2) 0.19180(17) 0.0226(4) Uani 1 1 d . . . C9 C -0.0676(2) 0.7116(2) 0.11892(17) 0.0232(4) Uani 1 1 d . . . C10 C -0.0984(2) 0.7574(2) -0.01716(19) 0.0279(4) Uani 1 1 d . . . C11 C -0.2105(3) 0.9190(2) -0.0818(2) 0.0312(5) Uani 1 1 d . . . C12 C -0.2876(3) 1.0332(2) -0.00976(19) 0.0301(5) Uani 1 1 d . . . C13 C -0.2525(2) 0.9889(2) 0.12494(18) 0.0264(4) Uani 1 1 d . . . C14 C -0.2640(3) 0.8355(3) 0.4246(2) 0.0273(4) Uani 1 1 d . . . C15 C -0.2404(2) 0.9803(2) 0.47113(19) 0.0273(4) Uani 1 1 d . . . HO2 H -0.123(3) 1.167(3) 0.4174(19) 0.047(6) Uiso 1 1 d . . . H3 H 0.351(2) 0.392(2) 0.1078(17) 0.028(5) Uiso 1 1 d . . . H4 H 0.638(3) 0.385(2) 0.1693(17) 0.033(5) Uiso 1 1 d . . . H5 H 0.665(2) 0.525(2) 0.3233(16) 0.025(5) Uiso 1 1 d . . . H6 H 0.385(2) 0.675(2) 0.4124(17) 0.028(5) Uiso 1 1 d . . . H10 H -0.047(3) 0.679(3) -0.0600(19) 0.041(6) Uiso 1 1 d . . . H11 H -0.230(2) 0.950(2) -0.1781(17) 0.022(4) Uiso 1 1 d . . . H12 H -0.360(2) 1.149(2) -0.0570(16) 0.026(5) Uiso 1 1 d . . . H13 H -0.303(2) 1.065(2) 0.1778(17) 0.025(5) Uiso 1 1 d . . . H14A H -0.273(2) 0.736(2) 0.5084(18) 0.030(5) Uiso 1 1 d . . . H14B H -0.378(3) 0.878(2) 0.3754(17) 0.035(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0312(8) 0.0291(7) 0.0234(7) -0.0112(5) -0.0037(5) -0.0065(5) O2 0.0354(8) 0.0303(7) 0.0322(8) -0.0161(6) -0.0042(6) -0.0071(6) O3 0.0334(8) 0.0495(8) 0.0329(8) -0.0254(7) 0.0010(6) -0.0060(6) O4 0.0279(7) 0.0246(6) 0.0293(7) -0.0123(5) -0.0067(5) -0.0034(5) N1 0.0215(8) 0.0262(8) 0.0212(8) -0.0104(6) -0.0016(6) -0.0036(6) C1 0.0216(10) 0.0202(9) 0.0215(10) -0.0054(7) -0.0030(7) -0.0032(7) C2 0.0258(10) 0.0215(9) 0.0249(10) -0.0075(8) -0.0051(8) -0.0049(7) C3 0.0309(11) 0.0269(10) 0.0264(11) -0.0129(9) -0.0026(8) -0.0032(8) C4 0.0250(11) 0.0273(10) 0.0341(12) -0.0111(9) 0.0003(9) 0.0011(8) C5 0.0251(11) 0.0281(10) 0.0283(11) -0.0058(8) -0.0039(9) -0.0066(8) C6 0.0288(11) 0.0226(9) 0.0223(10) -0.0063(8) -0.0046(8) -0.0051(8) C7 0.0256(10) 0.0206(9) 0.0217(10) -0.0067(7) -0.0022(8) -0.0076(7) C8 0.0222(10) 0.0262(9) 0.0218(10) -0.0077(8) -0.0027(7) -0.0091(7) C9 0.0201(10) 0.0247(9) 0.0264(10) -0.0084(8) -0.0045(8) -0.0059(7) C10 0.0260(11) 0.0342(11) 0.0294(11) -0.0160(9) -0.0019(8) -0.0091(9) C11 0.0322(11) 0.0373(11) 0.0249(11) -0.0065(9) -0.0067(9) -0.0119(9) C12 0.0283(11) 0.0265(10) 0.0332(12) -0.0047(9) -0.0066(9) -0.0069(9) C13 0.0238(10) 0.0254(10) 0.0314(11) -0.0108(9) -0.0039(8) -0.0045(8) C14 0.0242(11) 0.0306(10) 0.0269(11) -0.0116(9) -0.0012(9) -0.0033(8) C15 0.0230(10) 0.0300(10) 0.0284(11) -0.0117(9) -0.0078(8) 0.0017(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C7 1.2407(19) . ? O2 C15 1.336(2) . ? O3 C15 1.211(2) . ? O4 C2 1.388(2) . ? O4 C9 1.402(2) . ? N1 C7 1.362(2) . ? N1 C8 1.431(2) . ? N1 C14 1.466(2) . ? C1 C2 1.395(2) . ? C1 C6 1.397(2) . ? C1 C7 1.489(2) . ? C2 C3 1.385(2) . ? C3 C4 1.382(3) . ? C4 C5 1.383(3) . ? C5 C6 1.381(3) . ? C8 C9 1.386(2) . ? C8 C13 1.394(2) . ? C9 C10 1.384(2) . ? C10 C11 1.387(3) . ? C11 C12 1.380(3) . ? C12 C13 1.381(2) . ? C14 C15 1.510(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 C2 O4 C9 113.75(12) . . ? C7 N1 C8 125.64(14) . . ? C7 N1 C14 114.99(15) . . ? C8 N1 C14 118.90(14) . . ? C2 C1 C6 118.17(16) . . ? C2 C1 C7 123.99(16) . . ? C6 C1 C7 117.46(16) . . ? C3 C2 O4 118.34(16) . . ? C3 C2 C1 120.80(17) . . ? O4 C2 C1 120.83(15) . . ? C4 C3 C2 119.65(18) . . ? C3 C4 C5 120.74(18) . . ? C6 C5 C4 119.24(19) . . ? C5 C6 C1 121.36(18) . . ? O1 C7 N1 119.41(16) . . ? O1 C7 C1 119.28(15) . . ? N1 C7 C1 121.27(15) . . ? C9 C8 C13 118.10(16) . . ? C9 C8 N1 121.71(14) . . ? C13 C8 N1 120.15(15) . . ? C10 C9 C8 121.45(16) . . ? C10 C9 O4 118.26(16) . . ? C8 C9 O4 120.22(15) . . ? C9 C10 C11 119.73(18) . . ? C12 C11 C10 119.38(18) . . ? C11 C12 C13 120.69(18) . . ? C12 C13 C8 120.61(18) . . ? N1 C14 C15 115.29(15) . . ? O3 C15 O2 123.93(17) . . ? O3 C15 C14 122.58(17) . . ? O2 C15 C14 113.45(16) . . ? _diffrn_measured_fraction_theta_max 0.866 _diffrn_reflns_theta_full 25.000 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.243 _refine_diff_density_min -0.194 _refine_diff_density_rms 0.049 #===END data_2 _database_code_depnum_ccdc_archive 'CCDC 685694' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H11 N O3 S' _chemical_formula_weight 285.31 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 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 7.7680(9) _cell_length_b 11.736(1) _cell_length_c 14.923(2) _cell_angle_alpha 90.00 _cell_angle_beta 104.66(1) _cell_angle_gamma 90.00 _cell_volume 1316.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150 _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.440 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 592 _exptl_absorpt_coefficient_mu 2.252 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.29.2 (release 20-01-2006 CrysAlis171 .NET) (compiled Jan 20 2006,12:36:28) ; _diffrn_ambient_temperature 150 _diffrn_radiation_wavelength 1.54018 _diffrn_radiation_type ? _diffrn_radiation_source 'Enhance (Cu) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur3 4 circles diffractometer' _diffrn_measurement_method 'intensity 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 8055 _diffrn_reflns_av_R_equivalents 0.0700 _diffrn_reflns_av_sigmaI/netI 0.3092 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 8.14 _diffrn_reflns_theta_max 88.06 _reflns_number_total 2807 _reflns_number_gt 1018 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.29.2 (release 20-01-2006 CrysAlis171 .NET) (compiled Jan 20 2006,12:36:28) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.29.2 (release 20-01-2006 CrysAlis171 .NET) (compiled Jan 20 2006,12:36:28) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.29.2 (release 20-01-2006 CrysAlis171 .NET) (compiled Jan 20 2006,12:36:28) ; _computing_structure_solution 'SIR97 (Altomare, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farruggia, 1997)' _computing_publication_material 'PARST97 (Nardelli, 1995)' _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^)+(0.0408P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2807 _refine_ls_number_parameters 185 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1361 _refine_ls_R_factor_gt 0.0555 _refine_ls_wR_factor_ref 0.1194 _refine_ls_wR_factor_gt 0.1117 _refine_ls_goodness_of_fit_ref 0.887 _refine_ls_restrained_S_all 0.887 _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 0.13227(14) -0.05069(9) 0.63337(7) 0.0374(3) Uani 1 1 d . . . O1 O 0.4525(3) -0.1374(2) 0.90000(17) 0.0305(7) Uani 1 1 d . . . O2 O 0.0689(4) -0.1555(3) 0.87435(18) 0.0346(8) Uani 1 1 d . . . O3 O 0.1380(3) -0.1145(2) 1.02520(17) 0.0412(8) Uani 1 1 d . . . N1 N 0.2834(4) 0.0109(3) 0.83762(18) 0.0245(8) Uani 1 1 d . . . C1 C 0.4677(5) -0.0874(3) 0.7475(2) 0.0270(10) Uani 1 1 d . . . C2 C 0.3626(5) -0.0840(3) 0.6584(3) 0.0283(10) Uani 1 1 d . . . C3 C 0.4349(5) -0.1093(3) 0.5838(3) 0.0342(11) Uani 1 1 d . . . H3 H 0.3634 -0.1088 0.5235 0.041 Uiso 1 1 calc R . . C4 C 0.6151(6) -0.1352(3) 0.6010(3) 0.0380(12) Uani 1 1 d . . . H4 H 0.6649 -0.1512 0.5519 0.046 Uiso 1 1 calc R . . C5 C 0.7200(6) -0.1373(3) 0.6904(3) 0.0345(11) Uani 1 1 d . . . H5 H 0.8403 -0.1546 0.7012 0.041 Uiso 1 1 calc R . . C6 C 0.6491(5) -0.1143(3) 0.7637(3) 0.0276(10) Uani 1 1 d . . . H6 H 0.7207 -0.1165 0.8239 0.033 Uiso 1 1 calc R . . C7 C 0.4007(5) -0.0726(4) 0.8331(3) 0.0288(10) Uani 1 1 d . . . C8 C 0.2338(5) 0.1043(3) 0.7740(3) 0.0252(10) Uani 1 1 d . . . C9 C 0.1555(5) 0.0878(3) 0.6811(2) 0.0259(10) Uani 1 1 d . . . C10 C 0.1000(5) 0.1826(4) 0.6259(2) 0.0350(11) Uani 1 1 d . . . H10 H 0.0489 0.1725 0.5630 0.042 Uiso 1 1 calc R . . C11 C 0.1182(5) 0.2907(4) 0.6615(3) 0.0400(12) Uani 1 1 d . . . H11 H 0.0747 0.3528 0.6239 0.048 Uiso 1 1 calc R . . C12 C 0.2019(6) 0.3066(4) 0.7542(3) 0.0424(12) Uani 1 1 d . . . H12 H 0.2178 0.3799 0.7786 0.051 Uiso 1 1 calc R . . C13 C 0.2617(5) 0.2141(3) 0.8105(3) 0.0343(11) Uani 1 1 d . . . H13 H 0.3205 0.2250 0.8724 0.041 Uiso 1 1 calc R . . C14 C 0.2244(5) 0.0163(3) 0.9233(2) 0.0278(10) Uani 1 1 d . . . H14A H 0.1386 0.0775 0.9180 0.033 Uiso 1 1 calc R . . H14B H 0.3258 0.0348 0.9742 0.033 Uiso 1 1 calc R . . C15 C 0.1416(5) -0.0922(3) 0.9464(3) 0.0278(10) Uani 1 1 d . . . H2O H 0.037(6) -0.229(5) 0.890(3) 0.12(2) 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 S1 0.0313(7) 0.0420(8) 0.0373(6) -0.0058(5) 0.0056(5) 0.0000(6) O1 0.0288(18) 0.0284(19) 0.0330(16) 0.0044(13) 0.0055(15) 0.0078(14) O2 0.0343(19) 0.032(2) 0.0375(18) 0.0016(15) 0.0086(16) -0.0066(15) O3 0.054(2) 0.0363(19) 0.0342(17) 0.0042(13) 0.0126(16) 0.0052(15) N1 0.025(2) 0.023(2) 0.0268(18) 0.0012(15) 0.0094(17) 0.0049(17) C1 0.027(3) 0.027(3) 0.030(2) -0.0008(19) 0.012(2) 0.002(2) C2 0.034(3) 0.015(3) 0.043(3) -0.0023(19) 0.023(2) -0.007(2) C3 0.041(3) 0.029(3) 0.033(2) -0.001(2) 0.010(2) -0.006(2) C4 0.042(3) 0.032(3) 0.047(3) -0.003(2) 0.023(3) 0.002(2) C5 0.028(3) 0.025(3) 0.054(3) 0.002(2) 0.016(3) 0.001(2) C6 0.027(3) 0.023(3) 0.034(2) -0.0058(19) 0.010(2) -0.005(2) C7 0.022(3) 0.029(3) 0.034(3) -0.007(2) 0.005(2) -0.008(2) C8 0.025(2) 0.019(3) 0.033(2) 0.0049(19) 0.010(2) 0.006(2) C9 0.020(2) 0.030(3) 0.029(2) 0.0021(19) 0.010(2) 0.003(2) C10 0.039(3) 0.044(3) 0.024(2) 0.008(2) 0.010(2) 0.004(3) C11 0.050(3) 0.031(3) 0.041(3) 0.018(2) 0.017(3) 0.018(3) C12 0.055(3) 0.021(3) 0.056(3) 0.006(2) 0.023(3) 0.012(2) C13 0.039(3) 0.030(3) 0.037(3) -0.002(2) 0.017(2) 0.002(2) C14 0.029(3) 0.024(3) 0.031(2) -0.0020(18) 0.010(2) 0.005(2) C15 0.031(3) 0.028(3) 0.026(2) 0.000(2) 0.010(2) 0.006(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 C9 1.765(4) . ? S1 C2 1.776(4) . ? O1 C7 1.239(4) . ? O2 C15 1.312(4) . ? O3 C15 1.212(4) . ? N1 C7 1.352(4) . ? N1 C8 1.436(4) . ? N1 C14 1.465(4) . ? C1 C2 1.373(5) . ? C1 C6 1.403(5) . ? C1 C7 1.507(4) . ? C2 C3 1.400(4) . ? C3 C4 1.392(5) . ? C4 C5 1.376(5) . ? C5 C6 1.370(4) . ? C8 C9 1.380(5) . ? C8 C13 1.395(5) . ? C9 C10 1.386(5) . ? C10 C11 1.369(5) . ? C11 C12 1.384(5) . ? C12 C13 1.379(5) . ? C14 C15 1.505(5) . ? 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 S1 C2 97.06(18) . . ? C7 N1 C8 126.3(3) . . ? C7 N1 C14 116.0(3) . . ? C8 N1 C14 116.9(3) . . ? C2 C1 C6 119.9(3) . . ? C2 C1 C7 124.6(3) . . ? C6 C1 C7 115.3(4) . . ? C1 C2 C3 120.2(4) . . ? C1 C2 S1 122.1(3) . . ? C3 C2 S1 117.7(3) . . ? C4 C3 C2 119.2(4) . . ? C5 C4 C3 120.3(4) . . ? C6 C5 C4 120.7(4) . . ? C5 C6 C1 119.7(4) . . ? O1 C7 N1 119.4(3) . . ? O1 C7 C1 120.1(4) . . ? N1 C7 C1 120.6(4) . . ? C9 C8 C13 120.4(3) . . ? C9 C8 N1 122.3(3) . . ? C13 C8 N1 117.3(3) . . ? C8 C9 C10 118.4(4) . . ? C8 C9 S1 120.6(3) . . ? C10 C9 S1 121.0(3) . . ? C11 C10 C9 121.9(4) . . ? C10 C11 C12 119.3(4) . . ? C13 C12 C11 120.3(4) . . ? C12 C13 C8 119.6(4) . . ? N1 C14 C15 114.2(3) . . ? O3 C15 O2 124.2(4) . . ? O3 C15 C14 121.4(4) . . ? O2 C15 C14 114.3(3) . . ? _diffrn_measured_fraction_theta_max 0.933 _diffrn_reflns_theta_full 70.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.372 _refine_diff_density_min -0.251 _refine_diff_density_rms 0.065 #===END data_3 _database_code_depnum_ccdc_archive 'CCDC 685695' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H13 N O6 S' _chemical_formula_weight 335.32 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 triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.117(1) _cell_length_b 8.432(1) _cell_length_c 11.705(2) _cell_angle_alpha 108.32(1) _cell_angle_beta 90.98(1) _cell_angle_gamma 99.13(1) _cell_volume 748.96(18) _cell_formula_units_Z 2 _cell_measurement_temperature 150 _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.4 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.487 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 348 _exptl_absorpt_coefficient_mu 0.248 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.29.2 (release 20-01-2006 CrysAlis171 .NET) (compiled Jan 20 2006,12:36:28) ; _diffrn_ambient_temperature 150 _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur3 4 circles diffractometer' _diffrn_measurement_method 'intensity from \w scans' _diffrn_detector_area_resol_mean 16.4547 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9073 _diffrn_reflns_av_R_equivalents 0.0206 _diffrn_reflns_av_sigmaI/netI 0.0250 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 4.32 _diffrn_reflns_theta_max 28.39 _reflns_number_total 3290 _reflns_number_gt 2612 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.29.2 (release 20-01-2006 CrysAlis171 .NET) (compiled Jan 20 2006,12:36:28) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.29.2 (release 20-01-2006 CrysAlis171 .NET) (compiled Jan 20 2006,12:36:28) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.29.2 (release 20-01-2006 CrysAlis171 .NET) (compiled Jan 20 2006,12:36:28) ; _computing_structure_solution 'SIR97 (Altomare, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farruggia, 1997)' _computing_publication_material 'PARST97 (Nardelli, 1995)' _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^)+(0.0791P)^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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3290 _refine_ls_number_parameters 260 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0507 _refine_ls_R_factor_gt 0.0415 _refine_ls_wR_factor_ref 0.1249 _refine_ls_wR_factor_gt 0.1159 _refine_ls_goodness_of_fit_ref 1.112 _refine_ls_restrained_S_all 1.112 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S -0.68340(5) 1.53454(5) 0.83256(4) 0.02377(16) Uani 1 1 d . . . O1 O -0.53178(15) 1.08586(14) 0.66069(11) 0.0297(3) Uani 1 1 d . . . O2 O -0.08308(16) 1.05748(16) 0.75533(12) 0.0314(3) Uani 1 1 d . . . O3 O -0.12921(17) 1.21940(16) 0.64172(12) 0.0339(3) Uani 1 1 d . . . O4 O -0.72400(15) 1.39265(16) 0.87628(11) 0.0328(3) Uani 1 1 d . . . O5 O -0.77569(14) 1.67209(15) 0.87104(11) 0.0327(3) Uani 1 1 d . . . O1W O -0.13038(17) 1.07716(17) 0.38932(13) 0.0334(3) Uani 1 1 d . . . N1 N -0.38583(17) 1.33561(17) 0.77830(13) 0.0229(3) Uani 1 1 d . . . C1 C -0.60589(19) 1.32545(19) 0.62241(15) 0.0215(4) Uani 1 1 d . . . C2 C -0.69135(19) 1.4593(2) 0.67442(15) 0.0211(3) Uani 1 1 d . . . C3 C -0.7771(2) 1.5312(2) 0.60577(17) 0.0258(4) Uani 1 1 d . . . C4 C -0.7803(2) 1.4664(2) 0.48039(17) 0.0286(4) Uani 1 1 d . . . C5 C -0.7009(2) 1.3300(2) 0.42720(16) 0.0282(4) Uani 1 1 d . . . C6 C -0.6150(2) 1.2590(2) 0.49640(16) 0.0255(4) Uani 1 1 d . . . C7 C -0.5094(2) 1.2420(2) 0.69053(15) 0.0232(4) Uani 1 1 d . . . C8 C -0.3473(2) 1.51573(19) 0.82885(14) 0.0205(3) Uani 1 1 d . . . C9 C -0.46903(19) 1.6191(2) 0.86362(14) 0.0206(3) Uani 1 1 d . . . C10 C -0.4249(2) 1.7935(2) 0.91828(16) 0.0272(4) Uani 1 1 d . . . C11 C -0.2586(2) 1.8676(2) 0.94272(17) 0.0307(4) Uani 1 1 d . . . C12 C -0.1364(2) 1.7675(2) 0.90812(17) 0.0303(4) Uani 1 1 d . . . C13 C -0.1794(2) 1.5935(2) 0.85125(15) 0.0253(4) Uani 1 1 d . . . C14 C -0.2798(2) 1.2356(2) 0.81963(16) 0.0245(4) Uani 1 1 d . . . C15 C -0.1555(2) 1.1701(2) 0.72749(15) 0.0232(4) Uani 1 1 d . . . H2O H -0.007(3) 1.025(3) 0.710(2) 0.050(7) Uiso 1 1 d . . . H1W H -0.236(4) 1.021(3) 0.379(3) 0.067(8) Uiso 1 1 d . . . H2W H -0.119(4) 1.124(3) 0.475(3) 0.076(9) Uiso 1 1 d . . . H3 H -0.826(3) 1.625(3) 0.6476(19) 0.041(6) Uiso 1 1 d . . . H4 H -0.843(3) 1.520(3) 0.437(2) 0.039(6) Uiso 1 1 d . . . H5 H -0.709(3) 1.289(2) 0.340(2) 0.041(6) Uiso 1 1 d . . . H6 H -0.557(2) 1.170(2) 0.4562(16) 0.022(4) Uiso 1 1 d . . . H10 H -0.516(2) 1.859(2) 0.9420(17) 0.027(5) Uiso 1 1 d . . . H11 H -0.229(3) 1.991(3) 0.978(2) 0.041(6) Uiso 1 1 d . . . H12 H -0.018(3) 1.818(2) 0.9246(18) 0.032(5) Uiso 1 1 d . . . H13 H -0.093(2) 1.522(2) 0.8272(16) 0.024(5) Uiso 1 1 d . . . H14A H -0.348(2) 1.138(3) 0.8341(18) 0.032(5) Uiso 1 1 d . . . H14B H -0.221(2) 1.300(2) 0.8922(18) 0.025(5) 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 S1 0.0176(2) 0.0287(3) 0.0214(2) 0.00234(18) 0.00298(16) 0.00521(17) O1 0.0327(7) 0.0213(6) 0.0336(7) 0.0051(5) -0.0010(6) 0.0081(5) O2 0.0317(7) 0.0326(7) 0.0367(8) 0.0149(6) 0.0104(6) 0.0169(6) O3 0.0421(8) 0.0363(7) 0.0308(7) 0.0148(6) 0.0123(6) 0.0193(6) O4 0.0283(7) 0.0414(7) 0.0276(7) 0.0127(6) 0.0039(5) -0.0012(6) O5 0.0215(6) 0.0375(7) 0.0318(7) -0.0027(6) 0.0024(5) 0.0123(5) O1W 0.0292(7) 0.0352(7) 0.0333(8) 0.0053(6) 0.0061(6) 0.0096(6) N1 0.0226(7) 0.0218(7) 0.0240(8) 0.0057(6) 0.0008(6) 0.0069(6) C1 0.0173(7) 0.0194(7) 0.0249(9) 0.0040(7) 0.0016(6) 0.0011(6) C2 0.0167(7) 0.0218(8) 0.0214(8) 0.0029(6) 0.0014(6) 0.0021(6) C3 0.0202(8) 0.0238(8) 0.0319(10) 0.0067(7) -0.0003(7) 0.0047(7) C4 0.0256(9) 0.0307(9) 0.0307(10) 0.0118(8) -0.0042(7) 0.0048(7) C5 0.0295(9) 0.0304(9) 0.0212(9) 0.0059(7) -0.0004(7) 0.0005(8) C6 0.0254(8) 0.0222(8) 0.0250(9) 0.0024(7) 0.0025(7) 0.0040(7) C7 0.0224(8) 0.0230(8) 0.0225(9) 0.0038(7) 0.0040(7) 0.0061(7) C8 0.0214(8) 0.0207(8) 0.0180(8) 0.0034(6) 0.0012(6) 0.0057(6) C9 0.0164(7) 0.0239(8) 0.0187(8) 0.0028(6) 0.0005(6) 0.0036(6) C10 0.0254(9) 0.0261(9) 0.0270(9) 0.0019(7) 0.0018(7) 0.0092(7) C11 0.0285(9) 0.0231(9) 0.0346(11) 0.0016(7) -0.0023(8) 0.0035(7) C12 0.0202(8) 0.0314(10) 0.0355(11) 0.0073(8) -0.0004(7) 0.0013(7) C13 0.0207(8) 0.0289(9) 0.0251(9) 0.0053(7) 0.0021(7) 0.0076(7) C14 0.0257(8) 0.0256(9) 0.0233(9) 0.0071(7) 0.0021(7) 0.0091(7) C15 0.0237(8) 0.0203(8) 0.0240(9) 0.0047(7) -0.0007(7) 0.0044(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 S1 O4 1.4379(13) . ? S1 O5 1.4381(12) . ? S1 C2 1.7544(17) . ? S1 C9 1.7578(16) . ? O1 C7 1.2331(19) . ? O2 C15 1.311(2) . ? O3 C15 1.211(2) . ? N1 C7 1.374(2) . ? N1 C8 1.426(2) . ? N1 C14 1.469(2) . ? C1 C2 1.399(2) . ? C1 C6 1.399(2) . ? C1 C7 1.501(2) . ? C2 C3 1.385(2) . ? C3 C4 1.394(3) . ? C4 C5 1.387(2) . ? C5 C6 1.385(3) . ? C8 C13 1.397(2) . ? C8 C9 1.402(2) . ? C9 C10 1.390(2) . ? C10 C11 1.379(2) . ? C11 C12 1.387(2) . ? C12 C13 1.390(2) . ? C14 C15 1.525(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 O5 118.92(8) . . ? O4 S1 C2 108.88(8) . . ? O5 S1 C2 109.53(8) . . ? O4 S1 C9 109.99(8) . . ? O5 S1 C9 108.22(7) . . ? C2 S1 C9 99.56(8) . . ? C7 N1 C8 127.30(14) . . ? C7 N1 C14 114.88(14) . . ? C8 N1 C14 117.77(14) . . ? C2 C1 C6 117.83(15) . . ? C2 C1 C7 125.44(15) . . ? C6 C1 C7 116.69(14) . . ? C3 C2 C1 122.33(15) . . ? C3 C2 S1 121.05(13) . . ? C1 C2 S1 116.62(13) . . ? C2 C3 C4 118.86(16) . . ? C5 C4 C3 119.59(16) . . ? C6 C5 C4 121.24(17) . . ? C5 C6 C1 120.08(16) . . ? O1 C7 N1 119.23(15) . . ? O1 C7 C1 119.41(15) . . ? N1 C7 C1 121.09(14) . . ? C13 C8 C9 117.83(14) . . ? C13 C8 N1 118.64(14) . . ? C9 C8 N1 123.43(14) . . ? C10 C9 C8 121.35(14) . . ? C10 C9 S1 117.40(12) . . ? C8 C9 S1 121.17(12) . . ? C11 C10 C9 120.04(15) . . ? C10 C11 C12 119.37(17) . . ? C11 C12 C13 120.96(16) . . ? C12 C13 C8 120.40(16) . . ? N1 C14 C15 111.69(14) . . ? O3 C15 O2 126.10(15) . . ? O3 C15 C14 123.11(15) . . ? O2 C15 C14 110.79(14) . . ? _diffrn_measured_fraction_theta_max 0.877 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.500 _refine_diff_density_min -0.391 _refine_diff_density_rms 0.062