# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_shelxl11a _database_code_depnum_ccdc_archive 'CCDC 923685' #TrackingRef 'CMPD_11a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H12 O3' _chemical_formula_weight 192.21 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' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_cell_setting monoclinic 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 8.6179(3) _cell_length_b 7.0392(3) _cell_length_c 30.2576(10) _cell_angle_alpha 90.00 _cell_angle_beta 91.859(3) _cell_angle_gamma 90.00 _cell_volume 1834.55(12) _cell_formula_units_Z 8 _cell_measurement_temperature 130.0(2) _cell_measurement_reflns_used 3867 _cell_measurement_theta_min 2.9200 _cell_measurement_theta_max 72.9175 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4035 _exptl_crystal_size_mid 0.2470 _exptl_crystal_size_min 0.1040 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.392 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 816 _exptl_absorpt_coefficient_mu 0.832 _exptl_absorpt_correction_T_min 0.93211 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 130.0(2) _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'Enhance (Cu) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Sapphire3' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7121 _diffrn_reflns_av_R_equivalents 0.0216 _diffrn_reflns_av_sigmaI/netI 0.0244 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -37 _diffrn_reflns_limit_l_max 36 _diffrn_reflns_theta_min 2.92 _diffrn_reflns_theta_max 73.07 _reflns_number_total 3586 _reflns_number_gt 2989 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0969P)^2^+0.1601P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0020(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3586 _refine_ls_number_parameters 262 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0523 _refine_ls_R_factor_gt 0.0444 _refine_ls_wR_factor_ref 0.1491 _refine_ls_wR_factor_gt 0.1315 _refine_ls_goodness_of_fit_ref 1.118 _refine_ls_restrained_S_all 1.118 _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 H1 H 0.420(3) 0.810(3) 0.2221(7) 0.039(6) Uiso 1 1 d . . . H' H 0.369(2) 0.085(3) 0.2578(7) 0.038(6) Uiso 1 1 d . . . O1 O 0.33589(12) 0.86814(15) 0.22204(4) 0.0217(3) Uani 1 1 d . . . O2 O 0.13007(19) 0.36096(18) 0.03692(4) 0.0411(4) Uani 1 1 d . . . C7 C 0.29817(17) 0.5427(2) 0.11927(5) 0.0196(3) Uani 1 1 d . . . H7 H 0.3778 0.5766 0.0983 0.024 Uiso 1 1 calc R . . O3 O 0.16935(18) 0.08603(18) 0.07213(4) 0.0385(4) Uani 1 1 d . . . C9 C 0.20867(16) 0.7388(2) 0.22352(5) 0.0188(3) Uani 1 1 d . . . H9A H 0.1128 0.8102 0.2252 0.023 Uiso 1 1 calc R . . H9B H 0.2196 0.6620 0.2501 0.023 Uiso 1 1 calc R . . C6 C 0.33094(17) 0.4735(2) 0.16791(5) 0.0186(3) Uani 1 1 d . . . H6 H 0.4341 0.4592 0.1821 0.022 Uiso 1 1 calc R . . C3 C 0.04455(17) 0.5157(2) 0.12844(5) 0.0193(3) Uani 1 1 d . . . H3 H -0.0585 0.5302 0.1142 0.023 Uiso 1 1 calc R . . C4 C 0.17598(17) 0.3779(2) 0.11267(5) 0.0193(3) Uani 1 1 d . . . C1 C 0.19916(16) 0.6109(2) 0.18401(5) 0.0170(3) Uani 1 1 d . . . C2 C 0.07742(16) 0.4470(2) 0.17703(4) 0.0168(3) Uani 1 1 d . . . H2 H -0.0024 0.4129 0.1980 0.020 Uiso 1 1 calc R . . C5 C 0.20863(16) 0.3100(2) 0.16123(5) 0.0180(3) Uani 1 1 d . . . H5 H 0.2231 0.1777 0.1706 0.022 Uiso 1 1 calc R . . C8 C 0.16795(17) 0.6784(2) 0.13511(5) 0.0194(3) Uani 1 1 d . . . H8 H 0.1537 0.8106 0.1257 0.023 Uiso 1 1 calc R . . C10 C 0.15949(17) 0.2559(2) 0.07283(5) 0.0207(3) Uani 1 1 d . . . C11 C 0.1124(3) 0.2597(3) -0.00460(5) 0.0411(5) Uani 1 1 d . . . H11A H 0.0915 0.3486 -0.0281 0.062 Uiso 1 1 calc R . . H11B H 0.0276 0.1717 -0.0030 0.062 Uiso 1 1 calc R . . H11C H 0.2062 0.1916 -0.0102 0.062 Uiso 1 1 calc R . . O1' O 0.38603(12) 0.17805(16) 0.27448(4) 0.0251(3) Uani 1 1 d . . . C5' C 0.27072(17) 0.6995(2) 0.34767(5) 0.0185(3) Uani 1 1 d . . . H5' H 0.2512 0.8319 0.3392 0.022 Uiso 1 1 calc R . . C9' C 0.24532(16) 0.2712(2) 0.28513(5) 0.0184(3) Uani 1 1 d . . . H9D H 0.1675 0.1778 0.2924 0.022 Uiso 1 1 calc R . . H9C H 0.2065 0.3440 0.2599 0.022 Uiso 1 1 calc R . . O5 O 0.36429(18) 0.64536(17) 0.47087(4) 0.0381(4) Uani 1 1 d . . . C4' C 0.31838(17) 0.6295(2) 0.39512(5) 0.0192(3) Uani 1 1 d . . . C6' C 0.39703(16) 0.5671(2) 0.32764(5) 0.0175(3) Uani 1 1 d . . . H6' H 0.4685 0.6042 0.3046 0.021 Uiso 1 1 calc R . . C2' C 0.14865(16) 0.5330(2) 0.34383(5) 0.0188(3) Uani 1 1 d . . . H2' H 0.0413 0.5458 0.3325 0.023 Uiso 1 1 calc R . . C7' C 0.44674(17) 0.4968(2) 0.37502(5) 0.0199(3) Uani 1 1 d . . . H7' H 0.5540 0.4843 0.3864 0.024 Uiso 1 1 calc R . . O6 O 0.34893(19) 0.92132(18) 0.43473(4) 0.0431(4) Uani 1 1 d . . . C3' C 0.19855(17) 0.4624(2) 0.39119(5) 0.0212(3) Uani 1 1 d . . . H3' H 0.1272 0.4247 0.4142 0.025 Uiso 1 1 calc R . . C1' C 0.27519(16) 0.4003(2) 0.32361(5) 0.0170(3) Uani 1 1 d . . . C10' C 0.34475(17) 0.7510(2) 0.43466(5) 0.0215(3) Uani 1 1 d . . . C8' C 0.32522(17) 0.3313(2) 0.37124(5) 0.0199(3) Uani 1 1 d . . . H8' H 0.3450 0.1990 0.3798 0.024 Uiso 1 1 calc R . . C11' C 0.3910(3) 0.7463(3) 0.51208(5) 0.0391(5) Uani 1 1 d . . . H11E H 0.4037 0.6567 0.5358 0.059 Uiso 1 1 calc R . . H11F H 0.3038 0.8271 0.5175 0.059 Uiso 1 1 calc R . . H11D H 0.4831 0.8222 0.5103 0.059 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 O1 0.0187(5) 0.0163(5) 0.0301(6) -0.0049(4) 0.0005(4) -0.0018(4) O2 0.0826(10) 0.0211(6) 0.0188(6) -0.0027(5) -0.0102(6) 0.0036(6) C7 0.0207(7) 0.0193(7) 0.0189(7) -0.0002(5) 0.0017(5) -0.0025(6) O3 0.0696(9) 0.0213(6) 0.0243(6) -0.0014(5) -0.0030(6) 0.0017(6) C9 0.0187(7) 0.0185(7) 0.0193(7) -0.0010(5) 0.0008(5) -0.0015(5) C6 0.0185(7) 0.0171(7) 0.0201(7) -0.0020(5) -0.0020(5) -0.0002(6) C3 0.0205(7) 0.0191(7) 0.0180(7) 0.0000(5) -0.0028(5) 0.0008(6) C4 0.0223(7) 0.0175(7) 0.0178(7) 0.0004(5) -0.0020(5) -0.0010(6) C1 0.0179(7) 0.0150(7) 0.0180(7) -0.0003(5) -0.0009(5) -0.0014(5) C2 0.0166(6) 0.0163(7) 0.0173(6) 0.0001(5) -0.0009(5) -0.0011(5) C5 0.0202(7) 0.0156(7) 0.0179(7) -0.0004(5) -0.0018(5) -0.0005(5) C8 0.0243(7) 0.0153(7) 0.0186(7) 0.0011(5) -0.0007(5) -0.0006(6) C10 0.0227(7) 0.0192(7) 0.0202(7) -0.0008(6) -0.0004(5) -0.0012(6) C11 0.0748(14) 0.0294(9) 0.0185(8) -0.0056(7) -0.0086(8) 0.0022(9) O1' 0.0190(5) 0.0233(6) 0.0327(6) -0.0127(5) -0.0005(4) 0.0006(4) C5' 0.0222(7) 0.0151(7) 0.0180(7) 0.0002(5) -0.0004(5) 0.0019(5) C9' 0.0157(7) 0.0181(7) 0.0213(7) -0.0010(6) -0.0021(5) 0.0000(5) O5 0.0742(10) 0.0220(6) 0.0175(6) -0.0017(5) -0.0082(6) 0.0010(6) C4' 0.0226(7) 0.0185(7) 0.0167(7) 0.0002(6) 0.0002(5) 0.0015(6) C6' 0.0184(7) 0.0165(7) 0.0176(6) -0.0010(5) 0.0005(5) 0.0002(5) C2' 0.0179(7) 0.0185(7) 0.0201(7) -0.0004(5) -0.0002(5) 0.0015(6) C7' 0.0213(7) 0.0191(7) 0.0191(7) -0.0016(5) -0.0033(5) 0.0026(6) O6 0.0827(11) 0.0214(6) 0.0248(6) -0.0012(5) -0.0047(6) -0.0043(6) C3' 0.0225(7) 0.0226(7) 0.0187(7) 0.0015(6) 0.0025(5) -0.0025(6) C1' 0.0171(7) 0.0158(7) 0.0179(7) 0.0006(5) -0.0001(5) 0.0011(5) C10' 0.0248(7) 0.0211(8) 0.0186(7) -0.0001(6) 0.0012(6) -0.0003(6) C8' 0.0245(7) 0.0159(7) 0.0192(7) 0.0013(5) -0.0020(5) 0.0003(6) C11' 0.0686(13) 0.0300(9) 0.0182(8) -0.0037(7) -0.0070(8) -0.0017(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 O1 C9 1.4271(17) . ? O1 H1 0.83(2) . ? O2 C10 1.3321(19) . ? O2 C11 1.4483(18) . ? C7 C8 1.561(2) . ? C7 C6 1.5674(18) . ? C7 C4 1.575(2) . ? C7 H7 0.9800 . ? O3 C10 1.199(2) . ? C9 C1 1.4964(19) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C6 C5 1.5691(19) . ? C6 C1 1.5809(19) . ? C6 H6 0.9800 . ? C3 C2 1.5647(18) . ? C3 C8 1.571(2) . ? C3 C4 1.577(2) . ? C3 H3 0.9800 . ? C4 C10 1.4832(19) . ? C4 C5 1.5621(18) . ? C1 C8 1.5688(18) . ? C1 C2 1.5692(19) . ? C2 C5 1.5724(19) . ? C2 H2 0.9800 . ? C5 H5 0.9800 . ? C8 H8 0.9800 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? O1' C9' 1.4247(17) . ? O1' H' 0.84(2) . ? C5' C4' 1.5603(18) . ? C5' C6' 1.5696(19) . ? C5' C2' 1.577(2) . ? C5' H5' 0.9800 . ? C9' C1' 1.4927(19) . ? C9' H9D 0.9700 . ? C9' H9C 0.9700 . ? O5 C10' 1.3303(19) . ? O5 C11' 1.4473(18) . ? C4' C10' 1.482(2) . ? C4' C3' 1.567(2) . ? C4' C7' 1.5844(19) . ? C6' C7' 1.5633(18) . ? C6' C1' 1.5771(19) . ? C6' H6' 0.9800 . ? C2' C3' 1.5635(19) . ? C2' C1' 1.5745(19) . ? C2' H2' 0.9800 . ? C7' C8' 1.568(2) . ? C7' H7' 0.9800 . ? O6 C10' 1.199(2) . ? C3' C8' 1.565(2) . ? C3' H3' 0.9800 . ? C1' C8' 1.5677(18) . ? C8' H8' 0.9800 . ? C11' H11E 0.9600 . ? C11' H11F 0.9600 . ? C11' H11D 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 C9 O1 H1 110.8(15) . . ? C10 O2 C11 116.51(13) . . ? C8 C7 C6 90.65(10) . . ? C8 C7 C4 90.30(11) . . ? C6 C7 C4 89.39(11) . . ? C8 C7 H7 125.2 . . ? C6 C7 H7 125.2 . . ? C4 C7 H7 125.2 . . ? O1 C9 C1 112.39(11) . . ? O1 C9 H9A 109.1 . . ? C1 C9 H9A 109.1 . . ? O1 C9 H9B 109.1 . . ? C1 C9 H9B 109.1 . . ? H9A C9 H9B 107.9 . . ? C7 C6 C5 90.42(10) . . ? C7 C6 C1 89.41(10) . . ? C5 C6 C1 90.13(10) . . ? C7 C6 H6 125.3 . . ? C5 C6 H6 125.3 . . ? C1 C6 H6 125.3 . . ? C2 C3 C8 90.19(10) . . ? C2 C3 C4 89.11(10) . . ? C8 C3 C4 89.85(11) . . ? C2 C3 H3 125.5 . . ? C8 C3 H3 125.5 . . ? C4 C3 H3 125.5 . . ? C10 C4 C5 126.64(13) . . ? C10 C4 C7 125.14(12) . . ? C5 C4 C7 90.39(10) . . ? C10 C4 C3 123.46(12) . . ? C5 C4 C3 90.73(11) . . ? C7 C4 C3 89.57(11) . . ? C9 C1 C8 125.08(12) . . ? C9 C1 C2 124.67(12) . . ? C8 C1 C2 90.12(10) . . ? C9 C1 C6 126.37(12) . . ? C8 C1 C6 89.86(10) . . ? C2 C1 C6 89.55(10) . . ? C3 C2 C1 89.95(10) . . ? C3 C2 C5 90.80(10) . . ? C1 C2 C5 90.44(10) . . ? C3 C2 H2 125.0 . . ? C1 C2 H2 125.0 . . ? C5 C2 H2 125.0 . . ? C4 C5 C6 89.80(10) . . ? C4 C5 C2 89.36(10) . . ? C6 C5 C2 89.87(10) . . ? C4 C5 H5 125.5 . . ? C6 C5 H5 125.5 . . ? C2 C5 H5 125.5 . . ? C7 C8 C1 90.09(10) . . ? C7 C8 C3 90.28(11) . . ? C1 C8 C3 89.72(10) . . ? C7 C8 H8 125.2 . . ? C1 C8 H8 125.2 . . ? C3 C8 H8 125.2 . . ? O3 C10 O2 123.44(14) . . ? O3 C10 C4 125.94(14) . . ? O2 C10 C4 110.62(13) . . ? O2 C11 H11A 109.5 . . ? O2 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? O2 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C9' O1' H' 111.1(15) . . ? C4' C5' C6' 90.16(10) . . ? C4' C5' C2' 89.32(10) . . ? C6' C5' C2' 89.98(10) . . ? C4' C5' H5' 125.4 . . ? C6' C5' H5' 125.4 . . ? C2' C5' H5' 125.4 . . ? O1' C9' C1' 109.28(11) . . ? O1' C9' H9D 109.8 . . ? C1' C9' H9D 109.8 . . ? O1' C9' H9C 109.8 . . ? C1' C9' H9C 109.8 . . ? H9D C9' H9C 108.3 . . ? C10' O5 C11' 116.56(13) . . ? C10' C4' C5' 126.11(13) . . ? C10' C4' C3' 125.31(12) . . ? C5' C4' C3' 90.80(11) . . ? C10' C4' C7' 124.03(12) . . ? C5' C4' C7' 89.94(10) . . ? C3' C4' C7' 89.70(11) . . ? C7' C6' C5' 90.38(10) . . ? C7' C6' C1' 89.83(10) . . ? C5' C6' C1' 90.20(10) . . ? C7' C6' H6' 125.2 . . ? C5' C6' H6' 125.2 . . ? C1' C6' H6' 125.2 . . ? C3' C2' C1' 89.67(10) . . ? C3' C2' C5' 90.33(10) . . ? C1' C2' C5' 90.04(10) . . ? C3' C2' H2' 125.3 . . ? C1' C2' H2' 125.3 . . ? C5' C2' H2' 125.3 . . ? C6' C7' C8' 90.33(10) . . ? C6' C7' C4' 89.51(10) . . ? C8' C7' C4' 89.60(11) . . ? C6' C7' H7' 125.4 . . ? C8' C7' H7' 125.4 . . ? C4' C7' H7' 125.4 . . ? C2' C3' C8' 90.48(10) . . ? C2' C3' C4' 89.55(11) . . ? C8' C3' C4' 90.32(11) . . ? C2' C3' H3' 125.2 . . ? C8' C3' H3' 125.2 . . ? C4' C3' H3' 125.2 . . ? C9' C1' C8' 124.32(12) . . ? C9' C1' C2' 124.06(11) . . ? C8' C1' C2' 89.99(10) . . ? C9' C1' C6' 127.65(12) . . ? C8' C1' C6' 89.83(10) . . ? C2' C1' C6' 89.79(10) . . ? O6 C10' O5 123.68(14) . . ? O6 C10' C4' 125.60(14) . . ? O5 C10' C4' 110.72(14) . . ? C3' C8' C1' 89.86(10) . . ? C3' C8' C7' 90.38(11) . . ? C1' C8' C7' 90.01(11) . . ? C3' C8' H8' 125.2 . . ? C1' C8' H8' 125.2 . . ? C7' C8' H8' 125.2 . . ? O5 C11' H11E 109.5 . . ? O5 C11' H11F 109.5 . . ? H11E C11' H11F 109.5 . . ? O5 C11' H11D 109.5 . . ? H11E C11' H11D 109.5 . . ? H11F C11' H11D 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C8 C7 C6 C5 90.09(11) . . . . ? C4 C7 C6 C5 -0.20(11) . . . . ? C8 C7 C6 C1 -0.04(10) . . . . ? C4 C7 C6 C1 -90.33(11) . . . . ? C8 C7 C4 C10 132.28(14) . . . . ? C6 C7 C4 C10 -137.07(14) . . . . ? C8 C7 C4 C5 -90.44(11) . . . . ? C6 C7 C4 C5 0.20(11) . . . . ? C8 C7 C4 C3 0.29(10) . . . . ? C6 C7 C4 C3 90.93(10) . . . . ? C2 C3 C4 C10 136.28(14) . . . . ? C8 C3 C4 C10 -133.52(14) . . . . ? C2 C3 C4 C5 -0.09(10) . . . . ? C8 C3 C4 C5 90.10(10) . . . . ? C2 C3 C4 C7 -90.48(10) . . . . ? C8 C3 C4 C7 -0.29(10) . . . . ? O1 C9 C1 C8 -63.86(17) . . . . ? O1 C9 C1 C2 176.87(12) . . . . ? O1 C9 C1 C6 57.03(19) . . . . ? C7 C6 C1 C9 -135.35(14) . . . . ? C5 C6 C1 C9 134.23(14) . . . . ? C7 C6 C1 C8 0.04(10) . . . . ? C5 C6 C1 C8 -90.38(10) . . . . ? C7 C6 C1 C2 90.17(10) . . . . ? C5 C6 C1 C2 -0.25(10) . . . . ? C8 C3 C2 C1 0.69(10) . . . . ? C4 C3 C2 C1 90.53(10) . . . . ? C8 C3 C2 C5 -89.75(11) . . . . ? C4 C3 C2 C5 0.09(10) . . . . ? C9 C1 C2 C3 133.76(14) . . . . ? C8 C1 C2 C3 -0.69(10) . . . . ? C6 C1 C2 C3 -90.55(10) . . . . ? C9 C1 C2 C5 -135.44(14) . . . . ? C8 C1 C2 C5 90.11(10) . . . . ? C6 C1 C2 C5 0.25(10) . . . . ? C10 C4 C5 C6 136.05(14) . . . . ? C7 C4 C5 C6 -0.20(11) . . . . ? C3 C4 C5 C6 -89.78(11) . . . . ? C10 C4 C5 C2 -134.07(14) . . . . ? C7 C4 C5 C2 89.67(10) . . . . ? C3 C4 C5 C2 0.09(10) . . . . ? C7 C6 C5 C4 0.20(11) . . . . ? C1 C6 C5 C4 89.61(10) . . . . ? C7 C6 C5 C2 -89.16(10) . . . . ? C1 C6 C5 C2 0.25(10) . . . . ? C3 C2 C5 C4 -0.09(10) . . . . ? C1 C2 C5 C4 -90.05(10) . . . . ? C3 C2 C5 C6 89.71(10) . . . . ? C1 C2 C5 C6 -0.25(10) . . . . ? C6 C7 C8 C1 0.04(10) . . . . ? C4 C7 C8 C1 89.43(10) . . . . ? C6 C7 C8 C3 -89.68(10) . . . . ? C4 C7 C8 C3 -0.29(10) . . . . ? C9 C1 C8 C7 136.25(14) . . . . ? C2 C1 C8 C7 -89.60(10) . . . . ? C6 C1 C8 C7 -0.04(10) . . . . ? C9 C1 C8 C3 -133.47(14) . . . . ? C2 C1 C8 C3 0.69(10) . . . . ? C6 C1 C8 C3 90.24(10) . . . . ? C2 C3 C8 C7 89.40(10) . . . . ? C4 C3 C8 C7 0.29(10) . . . . ? C2 C3 C8 C1 -0.69(10) . . . . ? C4 C3 C8 C1 -89.80(10) . . . . ? C11 O2 C10 O3 -1.0(3) . . . . ? C11 O2 C10 C4 179.54(15) . . . . ? C5 C4 C10 O3 -0.2(3) . . . . ? C7 C4 C10 O3 122.06(18) . . . . ? C3 C4 C10 O3 -120.92(19) . . . . ? C5 C4 C10 O2 179.18(14) . . . . ? C7 C4 C10 O2 -58.55(19) . . . . ? C3 C4 C10 O2 58.47(19) . . . . ? C6' C5' C4' C10' 134.14(14) . . . . ? C2' C5' C4' C10' -135.88(14) . . . . ? C6' C5' C4' C3' -89.33(11) . . . . ? C2' C5' C4' C3' 0.64(10) . . . . ? C6' C5' C4' C7' 0.36(10) . . . . ? C2' C5' C4' C7' 90.34(11) . . . . ? C4' C5' C6' C7' -0.37(11) . . . . ? C2' C5' C6' C7' -89.69(10) . . . . ? C4' C5' C6' C1' 89.47(10) . . . . ? C2' C5' C6' C1' 0.15(10) . . . . ? C4' C5' C2' C3' -0.64(10) . . . . ? C6' C5' C2' C3' 89.52(10) . . . . ? C4' C5' C2' C1' -90.31(10) . . . . ? C6' C5' C2' C1' -0.15(10) . . . . ? C5' C6' C7' C8' 89.96(11) . . . . ? C1' C6' C7' C8' -0.24(10) . . . . ? C5' C6' C7' C4' 0.36(10) . . . . ? C1' C6' C7' C4' -89.84(10) . . . . ? C10' C4' C7' C6' -135.63(14) . . . . ? C5' C4' C7' C6' -0.36(11) . . . . ? C3' C4' C7' C6' 90.43(11) . . . . ? C10' C4' C7' C8' 134.04(14) . . . . ? C5' C4' C7' C8' -90.70(11) . . . . ? C3' C4' C7' C8' 0.10(10) . . . . ? C1' C2' C3' C8' 0.35(10) . . . . ? C5' C2' C3' C8' -89.68(11) . . . . ? C1' C2' C3' C4' 90.67(11) . . . . ? C5' C2' C3' C4' 0.64(10) . . . . ? C10' C4' C3' C2' 136.42(14) . . . . ? C5' C4' C3' C2' -0.64(11) . . . . ? C7' C4' C3' C2' -90.58(10) . . . . ? C10' C4' C3' C8' -133.10(14) . . . . ? C5' C4' C3' C8' 89.84(10) . . . . ? C7' C4' C3' C8' -0.10(10) . . . . ? O1' C9' C1' C8' -64.84(17) . . . . ? O1' C9' C1' C2' 177.70(12) . . . . ? O1' C9' C1' C6' 56.64(18) . . . . ? C3' C2' C1' C9' 132.52(14) . . . . ? C5' C2' C1' C9' -137.15(14) . . . . ? C3' C2' C1' C8' -0.35(10) . . . . ? C5' C2' C1' C8' 89.97(10) . . . . ? C3' C2' C1' C6' -90.18(10) . . . . ? C5' C2' C1' C6' 0.14(10) . . . . ? C7' C6' C1' C9' -134.98(14) . . . . ? C5' C6' C1' C9' 134.64(14) . . . . ? C7' C6' C1' C8' 0.24(10) . . . . ? C5' C6' C1' C8' -90.14(10) . . . . ? C7' C6' C1' C2' 90.23(10) . . . . ? C5' C6' C1' C2' -0.15(10) . . . . ? C11' O5 C10' O6 0.4(3) . . . . ? C11' O5 C10' C4' -179.89(15) . . . . ? C5' C4' C10' O6 -8.3(3) . . . . ? C3' C4' C10' O6 -130.80(19) . . . . ? C7' C4' C10' O6 111.1(2) . . . . ? C5' C4' C10' O5 171.99(14) . . . . ? C3' C4' C10' O5 49.5(2) . . . . ? C7' C4' C10' O5 -68.61(18) . . . . ? C2' C3' C8' C1' -0.36(11) . . . . ? C4' C3' C8' C1' -89.90(10) . . . . ? C2' C3' C8' C7' 89.65(11) . . . . ? C4' C3' C8' C7' 0.10(10) . . . . ? C9' C1' C8' C3' -132.33(13) . . . . ? C2' C1' C8' C3' 0.35(10) . . . . ? C6' C1' C8' C3' 90.14(11) . . . . ? C9' C1' C8' C7' 137.28(13) . . . . ? C2' C1' C8' C7' -90.03(11) . . . . ? C6' C1' C8' C7' -0.24(10) . . . . ? C6' C7' C8' C3' -89.61(10) . . . . ? C4' C7' C8' C3' -0.10(10) . . . . ? C6' C7' C8' C1' 0.24(10) . . . . ? C4' C7' C8' C1' 89.76(10) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1' H' O1 0.84(2) 1.88(2) 2.7238(15) 177(2) 1_545 _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 73.07 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 0.365 _refine_diff_density_min -0.320 _refine_diff_density_rms 0.065 data_shelxl11b _database_code_depnum_ccdc_archive 'CCDC 923686' #TrackingRef 'CMPD_11b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H15 N O5' _chemical_formula_weight 313.30 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_space_group_name_H-M 'P -1' _symmetry_cell_setting triclinic loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.9852(10) _cell_length_b 10.5113(15) _cell_length_c 10.8498(11) _cell_angle_alpha 68.415(11) _cell_angle_beta 78.650(10) _cell_angle_gamma 80.137(12) _cell_volume 721.99(16) _cell_formula_units_Z 2 _cell_measurement_temperature 130.0 _cell_measurement_reflns_used 764 _cell_measurement_theta_min 3.8536 _cell_measurement_theta_max 29.0809 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.3343 _exptl_crystal_size_mid 0.2581 _exptl_crystal_size_min 0.1692 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.441 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 328 _exptl_absorpt_coefficient_mu 0.107 _exptl_absorpt_correction_T_min 0.79007 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.39 (release 18-08-2010 CrysAlis171 .NET) (compiled Aug 18 2010,17:42:00) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 130.0 _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'SuperNova (Mo) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5867 _diffrn_reflns_av_R_equivalents 0.0196 _diffrn_reflns_av_sigmaI/netI 0.0314 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.99 _diffrn_reflns_theta_max 29.23 _reflns_number_total 3374 _reflns_number_gt 2808 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.39 (release 18-08-2010 CrysAlis171 .NET) (compiled Aug 18 2010,17:42:00) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.39 (release 18-08-2010 CrysAlis171 .NET) (compiled Aug 18 2010,17:42:00) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.39 (release 18-08-2010 CrysAlis171 .NET) (compiled Aug 18 2010,17:42:00) ; _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0502P)^2^+0.2474P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.007(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3374 _refine_ls_number_parameters 209 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0519 _refine_ls_R_factor_gt 0.0425 _refine_ls_wR_factor_ref 0.1167 _refine_ls_wR_factor_gt 0.1080 _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 C1 C 0.2341(2) 0.72803(14) 0.37789(14) 0.0193(3) Uani 1 1 d . . . C2 C 0.1946(2) 0.87867(14) 0.37971(14) 0.0201(3) Uani 1 1 d . . . H2 H 0.1738 0.9618 0.3019 0.024 Uiso 1 1 calc R . . C3 C 0.0438(2) 0.83035(14) 0.51007(14) 0.0195(3) Uani 1 1 d . . . H3 H -0.0860 0.8789 0.5271 0.023 Uiso 1 1 calc R . . C4 C 0.2147(2) 0.79794(14) 0.59713(13) 0.0185(3) Uani 1 1 d . . . C5 C 0.3637(2) 0.84699(14) 0.46570(14) 0.0209(3) Uani 1 1 d . . . H5 H 0.4652 0.9073 0.4501 0.025 Uiso 1 1 calc R . . C6 C 0.4031(2) 0.69586(14) 0.46419(14) 0.0210(3) Uani 1 1 d . . . H6 H 0.5328 0.6473 0.4473 0.025 Uiso 1 1 calc R . . C7 C 0.2518(2) 0.64746(14) 0.59489(14) 0.0207(3) Uani 1 1 d . . . H7 H 0.2723 0.5640 0.6725 0.025 Uiso 1 1 calc R . . C8 C 0.0829(2) 0.67981(14) 0.50876(14) 0.0202(3) Uani 1 1 d . . . H8 H -0.0186 0.6197 0.5239 0.024 Uiso 1 1 calc R . . C9 C 0.2442(2) 0.68968(14) 0.25724(14) 0.0210(3) Uani 1 1 d . . . H9A H 0.1179 0.7131 0.2255 0.025 Uiso 1 1 calc R . . H9B H 0.3416 0.7375 0.1857 0.025 Uiso 1 1 calc R . . C10 C 0.1918(2) 0.83609(14) 0.71847(14) 0.0187(3) Uani 1 1 d . . . C11 C 0.29508(19) 0.47750(14) 0.21349(14) 0.0184(3) Uani 1 1 d . . . C12 C 0.3437(2) 0.33487(15) 0.26322(14) 0.0210(3) Uani 1 1 d . . . H12 H 0.3792 0.2926 0.3485 0.025 Uiso 1 1 calc R . . C13 C 0.3392(2) 0.25680(15) 0.18603(15) 0.0215(3) Uani 1 1 d . . . H13 H 0.3703 0.1618 0.2186 0.026 Uiso 1 1 calc R . . C14 C 0.2876(2) 0.32256(15) 0.05902(14) 0.0205(3) Uani 1 1 d . . . C15 C 0.2421(2) 0.46344(15) 0.00715(14) 0.0206(3) Uani 1 1 d . . . H15 H 0.2091 0.5052 -0.0788 0.025 Uiso 1 1 calc R . . C16 C 0.2462(2) 0.54202(14) 0.08501(14) 0.0196(3) Uani 1 1 d . . . H16 H 0.2165 0.6371 0.0515 0.024 Uiso 1 1 calc R . . C17 C 0.2326(3) 1.00676(17) 0.80216(17) 0.0315(4) Uani 1 1 d . . . H17A H 0.2858 1.0932 0.7727 0.047 Uiso 1 1 calc R . . H17B H 0.2990 0.9411 0.8730 0.047 Uiso 1 1 calc R . . H17C H 0.0950 1.0189 0.8344 0.047 Uiso 1 1 calc R . . N1 N 0.27304(18) 0.23980(13) -0.02039(13) 0.0258(3) Uani 1 1 d . . . O1 O 0.29838(15) 0.54352(10) 0.29936(10) 0.0226(2) Uani 1 1 d . . . O2 O 0.3073(2) 0.11398(12) 0.02861(13) 0.0397(3) Uani 1 1 d . . . O3 O 0.22708(18) 0.29888(12) -0.13338(11) 0.0353(3) Uani 1 1 d . . . O4 O 0.11639(16) 0.76969(11) 0.82820(10) 0.0265(3) Uani 1 1 d . . . O5 O 0.26000(16) 0.95701(10) 0.69104(10) 0.0245(2) 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 0.0242(7) 0.0186(7) 0.0183(7) -0.0092(5) -0.0036(6) -0.0040(5) C2 0.0276(7) 0.0179(7) 0.0167(6) -0.0070(5) -0.0041(6) -0.0039(5) C3 0.0226(7) 0.0188(7) 0.0190(7) -0.0081(5) -0.0045(6) -0.0021(5) C4 0.0230(7) 0.0171(6) 0.0173(6) -0.0074(5) -0.0049(5) -0.0019(5) C5 0.0249(7) 0.0226(7) 0.0199(7) -0.0110(6) -0.0028(6) -0.0069(5) C6 0.0229(7) 0.0233(7) 0.0208(7) -0.0124(6) -0.0050(6) -0.0002(5) C7 0.0277(7) 0.0171(6) 0.0190(7) -0.0078(5) -0.0051(6) -0.0013(5) C8 0.0250(7) 0.0187(7) 0.0203(7) -0.0097(5) -0.0029(6) -0.0053(5) C9 0.0268(7) 0.0190(7) 0.0194(7) -0.0087(5) -0.0047(6) -0.0024(5) C10 0.0197(7) 0.0183(6) 0.0197(7) -0.0078(5) -0.0064(5) 0.0005(5) C11 0.0175(6) 0.0226(7) 0.0191(7) -0.0118(5) -0.0024(5) -0.0030(5) C12 0.0212(7) 0.0229(7) 0.0203(7) -0.0085(6) -0.0060(6) -0.0007(5) C13 0.0201(7) 0.0207(7) 0.0258(7) -0.0113(6) -0.0028(6) -0.0012(5) C14 0.0188(7) 0.0254(7) 0.0226(7) -0.0150(6) -0.0007(6) -0.0041(5) C15 0.0198(7) 0.0265(7) 0.0181(6) -0.0107(6) -0.0026(5) -0.0030(5) C16 0.0208(7) 0.0203(7) 0.0196(7) -0.0085(5) -0.0032(5) -0.0031(5) C17 0.0405(9) 0.0324(9) 0.0321(8) -0.0235(7) -0.0058(7) -0.0030(7) N1 0.0269(7) 0.0294(7) 0.0281(7) -0.0186(6) -0.0046(5) -0.0014(5) O1 0.0327(6) 0.0193(5) 0.0207(5) -0.0111(4) -0.0095(4) 0.0001(4) O2 0.0597(8) 0.0271(6) 0.0419(7) -0.0225(5) -0.0152(6) 0.0032(5) O3 0.0496(7) 0.0376(7) 0.0286(6) -0.0208(5) -0.0125(5) -0.0018(5) O4 0.0320(6) 0.0291(6) 0.0195(5) -0.0091(4) -0.0016(4) -0.0069(4) O5 0.0352(6) 0.0213(5) 0.0221(5) -0.0123(4) -0.0042(4) -0.0057(4) _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 C9 1.4910(18) . ? C1 C6 1.5651(19) . ? C1 C8 1.5658(19) . ? C1 C2 1.5668(19) . ? C2 C3 1.5608(19) . ? C2 C5 1.565(2) . ? C3 C8 1.5639(19) . ? C3 C4 1.5816(19) . ? C4 C10 1.4842(18) . ? C4 C5 1.5627(19) . ? C4 C7 1.5669(18) . ? C5 C6 1.5706(19) . ? C6 C7 1.565(2) . ? C7 C8 1.563(2) . ? C9 O1 1.4369(17) . ? C10 O4 1.2040(17) . ? C10 O5 1.3433(17) . ? C11 O1 1.3564(16) . ? C11 C16 1.3900(19) . ? C11 C12 1.3988(19) . ? C12 C13 1.379(2) . ? C13 C14 1.384(2) . ? C14 C15 1.381(2) . ? C14 N1 1.4578(17) . ? C15 C16 1.3886(19) . ? C17 O5 1.4500(17) . ? N1 O2 1.2301(17) . ? N1 O3 1.2321(17) . ? 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 C1 C6 125.61(12) . . ? C9 C1 C8 124.93(12) . . ? C6 C1 C8 90.07(10) . . ? C9 C1 C2 124.98(12) . . ? C6 C1 C2 90.24(10) . . ? C8 C1 C2 90.08(10) . . ? C3 C2 C5 90.25(10) . . ? C3 C2 C1 89.82(10) . . ? C5 C2 C1 89.90(10) . . ? C2 C3 C8 90.37(10) . . ? C2 C3 C4 89.81(10) . . ? C8 C3 C4 89.72(10) . . ? C10 C4 C5 127.94(11) . . ? C10 C4 C7 125.43(12) . . ? C5 C4 C7 90.53(10) . . ? C10 C4 C3 122.50(11) . . ? C5 C4 C3 89.57(10) . . ? C7 C4 C3 89.59(10) . . ? C4 C5 C2 90.37(10) . . ? C4 C5 C6 89.56(10) . . ? C2 C5 C6 90.11(10) . . ? C1 C6 C7 89.85(10) . . ? C1 C6 C5 89.75(10) . . ? C7 C6 C5 90.30(10) . . ? C8 C7 C6 90.17(10) . . ? C8 C7 C4 90.30(10) . . ? C6 C7 C4 89.60(10) . . ? C7 C8 C3 90.39(10) . . ? C7 C8 C1 89.91(10) . . ? C3 C8 C1 89.74(10) . . ? O1 C9 C1 105.82(11) . . ? O4 C10 O5 123.32(13) . . ? O4 C10 C4 124.74(13) . . ? O5 C10 C4 111.91(12) . . ? O1 C11 C16 124.43(13) . . ? O1 C11 C12 115.17(12) . . ? C16 C11 C12 120.40(13) . . ? C13 C12 C11 120.12(13) . . ? C12 C13 C14 118.69(13) . . ? C15 C14 C13 122.14(13) . . ? C15 C14 N1 118.93(13) . . ? C13 C14 N1 118.89(13) . . ? C14 C15 C16 119.16(13) . . ? C15 C16 C11 119.48(13) . . ? O2 N1 O3 122.98(13) . . ? O2 N1 C14 118.42(13) . . ? O3 N1 C14 118.60(12) . . ? C11 O1 C9 118.55(11) . . ? C10 O5 C17 115.76(11) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C9 C1 C2 C3 134.35(14) . . . . ? C6 C1 C2 C3 -90.12(10) . . . . ? C8 C1 C2 C3 -0.06(10) . . . . ? C9 C1 C2 C5 -135.40(14) . . . . ? C6 C1 C2 C5 0.13(10) . . . . ? C8 C1 C2 C5 90.19(10) . . . . ? C5 C2 C3 C8 -89.84(10) . . . . ? C1 C2 C3 C8 0.06(10) . . . . ? C5 C2 C3 C4 -0.12(10) . . . . ? C1 C2 C3 C4 89.78(10) . . . . ? C2 C3 C4 C10 136.52(13) . . . . ? C8 C3 C4 C10 -133.11(13) . . . . ? C2 C3 C4 C5 0.12(10) . . . . ? C8 C3 C4 C5 90.49(10) . . . . ? C2 C3 C4 C7 -90.41(10) . . . . ? C8 C3 C4 C7 -0.04(10) . . . . ? C10 C4 C5 C2 -132.60(14) . . . . ? C7 C4 C5 C2 89.47(10) . . . . ? C3 C4 C5 C2 -0.12(10) . . . . ? C10 C4 C5 C6 137.29(14) . . . . ? C7 C4 C5 C6 -0.64(10) . . . . ? C3 C4 C5 C6 -90.23(10) . . . . ? C3 C2 C5 C4 0.12(10) . . . . ? C1 C2 C5 C4 -89.69(10) . . . . ? C3 C2 C5 C6 89.69(10) . . . . ? C1 C2 C5 C6 -0.13(10) . . . . ? C9 C1 C6 C7 -134.75(13) . . . . ? C8 C1 C6 C7 0.09(10) . . . . ? C2 C1 C6 C7 90.17(10) . . . . ? C9 C1 C6 C5 134.96(13) . . . . ? C8 C1 C6 C5 -90.20(10) . . . . ? C2 C1 C6 C5 -0.13(10) . . . . ? C4 C5 C6 C1 90.49(10) . . . . ? C2 C5 C6 C1 0.13(10) . . . . ? C4 C5 C6 C7 0.64(10) . . . . ? C2 C5 C6 C7 -89.72(10) . . . . ? C1 C6 C7 C8 -0.09(10) . . . . ? C5 C6 C7 C8 89.65(10) . . . . ? C1 C6 C7 C4 -90.39(10) . . . . ? C5 C6 C7 C4 -0.64(10) . . . . ? C10 C4 C7 C8 130.91(13) . . . . ? C5 C4 C7 C8 -89.52(10) . . . . ? C3 C4 C7 C8 0.04(10) . . . . ? C10 C4 C7 C6 -138.92(13) . . . . ? C5 C4 C7 C6 0.65(10) . . . . ? C3 C4 C7 C6 90.21(10) . . . . ? C6 C7 C8 C3 -89.65(10) . . . . ? C4 C7 C8 C3 -0.04(10) . . . . ? C6 C7 C8 C1 0.09(10) . . . . ? C4 C7 C8 C1 89.70(10) . . . . ? C2 C3 C8 C7 89.86(10) . . . . ? C4 C3 C8 C7 0.04(10) . . . . ? C2 C3 C8 C1 -0.06(10) . . . . ? C4 C3 C8 C1 -89.87(10) . . . . ? C9 C1 C8 C7 135.22(13) . . . . ? C6 C1 C8 C7 -0.09(10) . . . . ? C2 C1 C8 C7 -90.33(10) . . . . ? C9 C1 C8 C3 -134.39(14) . . . . ? C6 C1 C8 C3 90.30(10) . . . . ? C2 C1 C8 C3 0.06(10) . . . . ? C6 C1 C9 O1 55.04(17) . . . . ? C8 C1 C9 O1 -65.09(16) . . . . ? C2 C1 C9 O1 175.53(12) . . . . ? C5 C4 C10 O4 -158.43(14) . . . . ? C7 C4 C10 O4 -33.7(2) . . . . ? C3 C4 C10 O4 82.55(18) . . . . ? C5 C4 C10 O5 23.54(19) . . . . ? C7 C4 C10 O5 148.23(13) . . . . ? C3 C4 C10 O5 -95.48(15) . . . . ? O1 C11 C12 C13 178.00(12) . . . . ? C16 C11 C12 C13 -1.5(2) . . . . ? C11 C12 C13 C14 0.5(2) . . . . ? C12 C13 C14 C15 0.5(2) . . . . ? C12 C13 C14 N1 -176.97(12) . . . . ? C13 C14 C15 C16 -0.7(2) . . . . ? N1 C14 C15 C16 176.84(12) . . . . ? C14 C15 C16 C11 -0.3(2) . . . . ? O1 C11 C16 C15 -178.09(12) . . . . ? C12 C11 C16 C15 1.3(2) . . . . ? C15 C14 N1 O2 -177.52(13) . . . . ? C13 C14 N1 O2 0.1(2) . . . . ? C15 C14 N1 O3 2.5(2) . . . . ? C13 C14 N1 O3 -179.96(13) . . . . ? C16 C11 O1 C9 1.3(2) . . . . ? C12 C11 O1 C9 -178.11(12) . . . . ? C1 C9 O1 C11 172.03(11) . . . . ? O4 C10 O5 C17 -1.7(2) . . . . ? C4 C10 O5 C17 176.33(12) . . . . ? _diffrn_measured_fraction_theta_max 0.860 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.353 _refine_diff_density_min -0.278 _refine_diff_density_rms 0.047 data_shelxl11c _database_code_depnum_ccdc_archive 'CCDC 923687' #TrackingRef 'CMPD_11c.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H15 N O6' _chemical_formula_weight 341.31 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' _symmetry_space_group_name_H-M 'P -1' _symmetry_cell_setting triclinic loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.1260(6) _cell_length_b 8.7446(5) _cell_length_c 12.5714(7) _cell_angle_alpha 89.867(5) _cell_angle_beta 76.801(5) _cell_angle_gamma 62.719(7) _cell_volume 767.54(8) _cell_formula_units_Z 2 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used 3723 _cell_measurement_theta_min 6.2302 _cell_measurement_theta_max 73.2842 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4521 _exptl_crystal_size_mid 0.2596 _exptl_crystal_size_min 0.1100 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.477 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 356 _exptl_absorpt_coefficient_mu 0.945 _exptl_absorpt_correction_T_min 0.86347 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 130(2) _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'Enhance (Cu) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Sapphire3' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4671 _diffrn_reflns_av_R_equivalents 0.0165 _diffrn_reflns_av_sigmaI/netI 0.0173 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 6.24 _diffrn_reflns_theta_max 73.44 _reflns_number_total 2935 _reflns_number_gt 2675 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0693P)^2^+0.3691P] 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 2935 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0462 _refine_ls_R_factor_gt 0.0431 _refine_ls_wR_factor_ref 0.1196 _refine_ls_wR_factor_gt 0.1169 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.018 _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 0.7992(2) 0.86472(19) 0.20342(12) 0.0224(3) Uani 1 1 d . . . C2 C 0.8979(2) 0.9260(2) 0.10219(12) 0.0235(3) Uani 1 1 d . . . H2 H 0.8296 1.0111 0.0541 0.028 Uiso 1 1 calc R . . C3 C 1.0236(2) 0.94864(19) 0.17223(12) 0.0228(3) Uani 1 1 d . . . H3 H 1.0486 1.0502 0.1755 0.027 Uiso 1 1 calc R . . C4 C 1.1811(2) 0.75551(19) 0.13445(12) 0.0224(3) Uani 1 1 d . . . C5 C 1.0545(2) 0.7340(2) 0.06246(12) 0.0239(3) Uani 1 1 d . . . H5 H 1.1032 0.6774 -0.0152 0.029 Uiso 1 1 calc R . . C6 C 0.9560(2) 0.67240(19) 0.16306(12) 0.0240(3) Uani 1 1 d . . . H6 H 0.9310 0.5709 0.1595 0.029 Uiso 1 1 calc R . . C7 C 1.0812(2) 0.69521(19) 0.23406(12) 0.0236(3) Uani 1 1 d . . . H7 H 1.1480 0.6105 0.2828 0.028 Uiso 1 1 calc R . . C8 C 0.9252(2) 0.88755(19) 0.27294(12) 0.0227(3) Uani 1 1 d . . . H8 H 0.8771 0.9446 0.3504 0.027 Uiso 1 1 calc R . . C9 C 0.5889(2) 0.9276(2) 0.24091(12) 0.0250(3) Uani 1 1 d . . . H9A H 0.5200 1.0553 0.2579 0.030 Uiso 1 1 calc R . . H9B H 0.5427 0.8946 0.1829 0.030 Uiso 1 1 calc R . . C10 C 1.3911(2) 0.69071(19) 0.09529(12) 0.0233(3) Uani 1 1 d . . . C11 C 1.6290(2) 0.7303(2) -0.03333(14) 0.0327(4) Uani 1 1 d . . . H11A H 1.6400 0.8144 -0.0823 0.049 Uiso 1 1 calc R . . H11B H 1.6771 0.6186 -0.0769 0.049 Uiso 1 1 calc R . . H11C H 1.7045 0.7159 0.0201 0.049 Uiso 1 1 calc R . . C12 C 0.3830(2) 0.85550(19) 0.37033(12) 0.0233(3) Uani 1 1 d . . . C13 C 0.3538(2) 0.77764(19) 0.47479(12) 0.0226(3) Uani 1 1 d . . . C14 C 0.4845(2) 0.7214(2) 0.53901(13) 0.0259(3) Uani 1 1 d . . . H14 H 0.6009 0.7275 0.5158 0.031 Uiso 1 1 calc R . . C15 C 0.4449(2) 0.6564(2) 0.63712(13) 0.0287(3) Uani 1 1 d . . . H15 H 0.5349 0.6176 0.6806 0.034 Uiso 1 1 calc R . . C16 C 0.2745(2) 0.6477(2) 0.67216(13) 0.0285(3) Uani 1 1 d . . . H16 H 0.2456 0.6050 0.7397 0.034 Uiso 1 1 calc R . . C17 C 0.1484(2) 0.70297(19) 0.60575(13) 0.0255(3) Uani 1 1 d . . . C18 C 0.1837(2) 0.76753(19) 0.50761(12) 0.0233(3) Uani 1 1 d . . . H18 H 0.0945 0.8040 0.4637 0.028 Uiso 1 1 calc R . . N1 N -0.0342(2) 0.69712(18) 0.64081(12) 0.0330(3) Uani 1 1 d . . . O1 O 0.55617(15) 0.84615(15) 0.33954(9) 0.0271(3) Uani 1 1 d . . . O2 O 0.26203(16) 0.91991(16) 0.32066(10) 0.0326(3) Uani 1 1 d . . . O3 O -0.09103(18) 0.68721(17) 0.73845(11) 0.0426(3) Uani 1 1 d . . . O4 O -0.1196(2) 0.7039(2) 0.57157(12) 0.0509(4) Uani 1 1 d . . . O5 O 1.51239(15) 0.56394(15) 0.12146(10) 0.0319(3) Uani 1 1 d . . . O6 O 1.43024(15) 0.79220(14) 0.02434(9) 0.0286(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 C1 0.0180(7) 0.0266(7) 0.0222(7) 0.0056(6) -0.0038(5) -0.0108(6) C2 0.0175(7) 0.0289(8) 0.0226(7) 0.0073(6) -0.0033(5) -0.0104(6) C3 0.0174(7) 0.0250(7) 0.0238(7) 0.0040(5) -0.0023(5) -0.0095(6) C4 0.0192(7) 0.0251(7) 0.0217(7) 0.0038(5) -0.0038(5) -0.0101(6) C5 0.0194(7) 0.0297(8) 0.0210(7) 0.0018(6) -0.0032(5) -0.0111(6) C6 0.0214(7) 0.0262(7) 0.0252(7) 0.0054(6) -0.0055(6) -0.0121(6) C7 0.0194(7) 0.0272(7) 0.0231(7) 0.0065(6) -0.0045(5) -0.0105(6) C8 0.0172(7) 0.0275(7) 0.0212(7) 0.0031(5) -0.0023(5) -0.0099(6) C9 0.0198(7) 0.0318(8) 0.0232(7) 0.0072(6) -0.0043(6) -0.0125(6) C10 0.0208(7) 0.0272(7) 0.0205(7) 0.0015(5) -0.0039(5) -0.0107(6) C11 0.0219(8) 0.0388(9) 0.0319(8) 0.0036(7) 0.0024(6) -0.0140(7) C12 0.0169(7) 0.0253(7) 0.0257(7) -0.0007(6) -0.0016(5) -0.0100(6) C13 0.0179(7) 0.0241(7) 0.0227(7) -0.0008(5) -0.0007(5) -0.0094(6) C14 0.0174(7) 0.0280(8) 0.0289(8) 0.0001(6) -0.0030(6) -0.0091(6) C15 0.0243(8) 0.0290(8) 0.0294(8) 0.0033(6) -0.0093(6) -0.0086(6) C16 0.0289(8) 0.0252(7) 0.0254(7) 0.0043(6) -0.0016(6) -0.0102(6) C17 0.0195(7) 0.0249(7) 0.0292(8) 0.0007(6) 0.0008(6) -0.0112(6) C18 0.0183(7) 0.0249(7) 0.0247(7) 0.0004(5) -0.0032(5) -0.0095(6) N1 0.0241(7) 0.0312(7) 0.0415(8) 0.0060(6) 0.0005(6) -0.0152(6) O1 0.0183(5) 0.0394(6) 0.0246(5) 0.0092(4) -0.0042(4) -0.0151(5) O2 0.0225(5) 0.0465(7) 0.0322(6) 0.0132(5) -0.0093(5) -0.0180(5) O3 0.0321(6) 0.0415(7) 0.0456(8) 0.0170(6) 0.0047(5) -0.0169(6) O4 0.0360(7) 0.0776(11) 0.0528(8) 0.0044(7) -0.0080(6) -0.0395(8) O5 0.0200(5) 0.0339(6) 0.0347(6) 0.0088(5) -0.0055(4) -0.0076(5) O6 0.0182(5) 0.0326(6) 0.0296(6) 0.0077(4) -0.0013(4) -0.0097(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 C1 C9 1.4891(19) . ? C1 C8 1.565(2) . ? C1 C6 1.566(2) . ? C1 C2 1.5728(19) . ? C2 C5 1.563(2) . ? C2 C3 1.567(2) . ? C3 C8 1.5667(19) . ? C3 C4 1.568(2) . ? C4 C10 1.4858(19) . ? C4 C7 1.5590(19) . ? C4 C5 1.586(2) . ? C5 C6 1.5686(19) . ? C6 C7 1.572(2) . ? C7 C8 1.562(2) . ? C9 O1 1.4608(17) . ? C10 O5 1.2055(19) . ? C10 O6 1.3453(18) . ? C11 O6 1.4465(18) . ? C12 O2 1.2018(19) . ? C12 O1 1.3353(17) . ? C12 C13 1.499(2) . ? C13 C14 1.390(2) . ? C13 C18 1.393(2) . ? C14 C15 1.390(2) . ? C15 C16 1.391(2) . ? C16 C17 1.384(2) . ? C17 C18 1.381(2) . ? C17 N1 1.4728(19) . ? N1 O4 1.217(2) . ? N1 O3 1.227(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 C9 C1 C8 125.59(12) . . ? C9 C1 C6 125.97(13) . . ? C8 C1 C6 90.36(11) . . ? C9 C1 C2 124.04(12) . . ? C8 C1 C2 89.94(10) . . ? C6 C1 C2 89.95(11) . . ? C5 C2 C3 90.14(10) . . ? C5 C2 C1 89.89(11) . . ? C3 C2 C1 89.84(10) . . ? C8 C3 C2 90.06(10) . . ? C8 C3 C4 89.16(10) . . ? C2 C3 C4 90.52(11) . . ? C10 C4 C7 124.95(12) . . ? C10 C4 C3 126.75(12) . . ? C7 C4 C3 90.61(11) . . ? C10 C4 C5 124.04(12) . . ? C7 C4 C5 90.16(11) . . ? C3 C4 C5 89.27(11) . . ? C2 C5 C6 90.24(10) . . ? C2 C5 C4 90.06(11) . . ? C6 C5 C4 89.34(11) . . ? C1 C6 C5 89.91(11) . . ? C1 C6 C7 89.49(11) . . ? C5 C6 C7 90.31(10) . . ? C4 C7 C8 89.67(11) . . ? C4 C7 C6 90.19(11) . . ? C8 C7 C6 90.23(11) . . ? C7 C8 C1 89.91(11) . . ? C7 C8 C3 90.55(10) . . ? C1 C8 C3 90.16(11) . . ? O1 C9 C1 106.75(11) . . ? O5 C10 O6 123.64(13) . . ? O5 C10 C4 125.63(14) . . ? O6 C10 C4 110.73(12) . . ? O2 C12 O1 124.18(14) . . ? O2 C12 C13 123.10(13) . . ? O1 C12 C13 112.72(13) . . ? C14 C13 C18 120.36(14) . . ? C14 C13 C12 123.08(13) . . ? C18 C13 C12 116.54(13) . . ? C15 C14 C13 120.00(14) . . ? C14 C15 C16 120.51(14) . . ? C17 C16 C15 118.04(14) . . ? C18 C17 C16 122.92(14) . . ? C18 C17 N1 117.58(14) . . ? C16 C17 N1 119.49(14) . . ? C17 C18 C13 118.16(14) . . ? O4 N1 O3 124.27(14) . . ? O4 N1 C17 118.10(14) . . ? O3 N1 C17 117.63(15) . . ? C12 O1 C9 114.96(11) . . ? C10 O6 C11 116.75(12) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C9 C1 C2 C5 -135.31(14) . . . . ? C8 C1 C2 C5 90.14(11) . . . . ? C6 C1 C2 C5 -0.22(10) . . . . ? C9 C1 C2 C3 134.55(14) . . . . ? C8 C1 C2 C3 0.00(10) . . . . ? C6 C1 C2 C3 -90.36(11) . . . . ? C5 C2 C3 C8 -89.89(11) . . . . ? C1 C2 C3 C8 0.00(10) . . . . ? C5 C2 C3 C4 -0.73(10) . . . . ? C1 C2 C3 C4 89.17(11) . . . . ? C8 C3 C4 C10 -135.68(14) . . . . ? C2 C3 C4 C10 134.27(14) . . . . ? C8 C3 C4 C7 0.62(11) . . . . ? C2 C3 C4 C7 -89.43(10) . . . . ? C8 C3 C4 C5 90.76(10) . . . . ? C2 C3 C4 C5 0.71(10) . . . . ? C3 C2 C5 C6 90.06(10) . . . . ? C1 C2 C5 C6 0.22(10) . . . . ? C3 C2 C5 C4 0.72(10) . . . . ? C1 C2 C5 C4 -89.12(11) . . . . ? C10 C4 C5 C2 -136.23(14) . . . . ? C7 C4 C5 C2 89.89(11) . . . . ? C3 C4 C5 C2 -0.72(10) . . . . ? C10 C4 C5 C6 133.53(14) . . . . ? C7 C4 C5 C6 -0.35(11) . . . . ? C3 C4 C5 C6 -90.96(11) . . . . ? C9 C1 C6 C5 133.93(14) . . . . ? C8 C1 C6 C5 -89.72(10) . . . . ? C2 C1 C6 C5 0.22(10) . . . . ? C9 C1 C6 C7 -135.76(14) . . . . ? C8 C1 C6 C7 0.59(10) . . . . ? C2 C1 C6 C7 90.53(10) . . . . ? C2 C5 C6 C1 -0.22(10) . . . . ? C4 C5 C6 C1 89.84(11) . . . . ? C2 C5 C6 C7 -89.71(11) . . . . ? C4 C5 C6 C7 0.35(11) . . . . ? C10 C4 C7 C8 136.90(14) . . . . ? C3 C4 C7 C8 -0.62(11) . . . . ? C5 C4 C7 C8 -89.89(11) . . . . ? C10 C4 C7 C6 -132.87(14) . . . . ? C3 C4 C7 C6 89.62(11) . . . . ? C5 C4 C7 C6 0.35(11) . . . . ? C1 C6 C7 C4 -90.26(10) . . . . ? C5 C6 C7 C4 -0.35(11) . . . . ? C1 C6 C7 C8 -0.59(10) . . . . ? C5 C6 C7 C8 89.32(11) . . . . ? C4 C7 C8 C1 90.78(10) . . . . ? C6 C7 C8 C1 0.59(10) . . . . ? C4 C7 C8 C3 0.62(11) . . . . ? C6 C7 C8 C3 -89.57(11) . . . . ? C9 C1 C8 C7 136.02(14) . . . . ? C6 C1 C8 C7 -0.60(10) . . . . ? C2 C1 C8 C7 -90.55(10) . . . . ? C9 C1 C8 C3 -133.43(14) . . . . ? C6 C1 C8 C3 89.96(11) . . . . ? C2 C1 C8 C3 0.00(10) . . . . ? C2 C3 C8 C7 89.91(11) . . . . ? C4 C3 C8 C7 -0.62(11) . . . . ? C2 C3 C8 C1 0.00(11) . . . . ? C4 C3 C8 C1 -90.53(11) . . . . ? C8 C1 C9 O1 -58.50(18) . . . . ? C6 C1 C9 O1 63.43(18) . . . . ? C2 C1 C9 O1 -177.30(12) . . . . ? C7 C4 C10 O5 14.0(2) . . . . ? C3 C4 C10 O5 136.54(16) . . . . ? C5 C4 C10 O5 -104.44(18) . . . . ? C7 C4 C10 O6 -166.75(13) . . . . ? C3 C4 C10 O6 -44.19(19) . . . . ? C5 C4 C10 O6 74.82(18) . . . . ? O2 C12 C13 C14 -172.28(15) . . . . ? O1 C12 C13 C14 7.3(2) . . . . ? O2 C12 C13 C18 6.1(2) . . . . ? O1 C12 C13 C18 -174.32(12) . . . . ? C18 C13 C14 C15 -0.7(2) . . . . ? C12 C13 C14 C15 177.59(13) . . . . ? C13 C14 C15 C16 -0.3(2) . . . . ? C14 C15 C16 C17 1.0(2) . . . . ? C15 C16 C17 C18 -0.7(2) . . . . ? C15 C16 C17 N1 -179.42(14) . . . . ? C16 C17 C18 C13 -0.3(2) . . . . ? N1 C17 C18 C13 178.49(13) . . . . ? C14 C13 C18 C17 0.9(2) . . . . ? C12 C13 C18 C17 -177.43(13) . . . . ? C18 C17 N1 O4 19.3(2) . . . . ? C16 C17 N1 O4 -161.92(16) . . . . ? C18 C17 N1 O3 -160.09(14) . . . . ? C16 C17 N1 O3 18.7(2) . . . . ? O2 C12 O1 C9 2.4(2) . . . . ? C13 C12 O1 C9 -177.24(11) . . . . ? C1 C9 O1 C12 -165.39(12) . . . . ? O5 C10 O6 C11 8.4(2) . . . . ? C4 C10 O6 C11 -170.86(12) . . . . ? _diffrn_measured_fraction_theta_max 0.953 _diffrn_reflns_theta_full 73.44 _diffrn_measured_fraction_theta_full 0.953 _refine_diff_density_max 0.368 _refine_diff_density_min -0.290 _refine_diff_density_rms 0.047 data_shelxl11d _database_code_depnum_ccdc_archive 'CCDC 923688' #TrackingRef 'CMPD_11d.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H15 N O6' _chemical_formula_weight 341.31 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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_space_group_name_H-M 'P -1' _symmetry_cell_setting triclinic loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.5474(4) _cell_length_b 8.4100(5) _cell_length_c 13.9152(8) _cell_angle_alpha 102.757(5) _cell_angle_beta 90.682(4) _cell_angle_gamma 115.310(5) _cell_volume 773.07(8) _cell_formula_units_Z 2 _cell_measurement_temperature 130.0 _cell_measurement_reflns_used 3454 _cell_measurement_theta_min 3.0014 _cell_measurement_theta_max 29.1409 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.466 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 356 _exptl_absorpt_coefficient_mu 0.111 _exptl_absorpt_correction_T_min 0.83407 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.39 (release 18-08-2010 CrysAlis171 .NET) (compiled Aug 18 2010,17:42:00) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 130.0 _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'SuperNova (Mo) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7502 _diffrn_reflns_av_R_equivalents 0.0217 _diffrn_reflns_av_sigmaI/netI 0.0351 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.01 _diffrn_reflns_theta_max 29.21 _reflns_number_total 3639 _reflns_number_gt 2946 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.39 (release 18-08-2010 CrysAlis171 .NET) (compiled Aug 18 2010,17:42:00) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.39 (release 18-08-2010 CrysAlis171 .NET) (compiled Aug 18 2010,17:42:00) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.39 (release 18-08-2010 CrysAlis171 .NET) (compiled Aug 18 2010,17:42:00) ; _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0436P)^2^+0.3157P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.011(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3639 _refine_ls_number_parameters 227 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0564 _refine_ls_R_factor_gt 0.0426 _refine_ls_wR_factor_ref 0.1093 _refine_ls_wR_factor_gt 0.0982 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _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 0.8740(2) 0.1799(2) 0.15550(11) 0.0197(3) Uani 1 1 d . . . C2 C 0.7968(2) 0.2294(2) 0.06675(11) 0.0209(3) Uani 1 1 d . . . H2 H 0.8031 0.1830 -0.0036 0.025 Uiso 1 1 calc R . . C3 C 0.6032(2) 0.2026(2) 0.11502(11) 0.0217(3) Uani 1 1 d . . . H3 H 0.4692 0.1367 0.0796 0.026 Uiso 1 1 calc R . . C4 C 0.7013(2) 0.4063(2) 0.17322(11) 0.0197(3) Uani 1 1 d . . . C5 C 0.8968(2) 0.43408(19) 0.12490(11) 0.0201(3) Uani 1 1 d . . . H5 H 0.9746 0.5360 0.0965 0.024 Uiso 1 1 calc R . . C6 C 0.9740(2) 0.3844(2) 0.21350(11) 0.0208(3) Uani 1 1 d . . . H6 H 1.1080 0.4498 0.2488 0.025 Uiso 1 1 calc R . . C7 C 0.7810(2) 0.3584(2) 0.26180(11) 0.0226(3) Uani 1 1 d . . . H7 H 0.7750 0.4050 0.3321 0.027 Uiso 1 1 calc R . . C8 C 0.6801(2) 0.1536(2) 0.20377(11) 0.0226(3) Uani 1 1 d . . . H8 H 0.6021 0.0520 0.2323 0.027 Uiso 1 1 calc R . . C9 C 0.9752(2) 0.0603(2) 0.14548(11) 0.0222(3) Uani 1 1 d . . . H9A H 0.8861 -0.0628 0.1097 0.027 Uiso 1 1 calc R . . H9B H 1.0893 0.1047 0.1100 0.027 Uiso 1 1 calc R . . C10 C 0.6261(2) 0.5441(2) 0.18038(11) 0.0212(3) Uani 1 1 d . . . C11 C 0.4033(3) 0.6241(2) 0.10779(14) 0.0328(4) Uani 1 1 d . . . H11A H 0.2906 0.5724 0.0585 0.049 Uiso 1 1 calc R . . H11B H 0.5079 0.7242 0.0900 0.049 Uiso 1 1 calc R . . H11C H 0.3680 0.6662 0.1711 0.049 Uiso 1 1 calc R . . C12 C 1.1421(2) -0.02368(19) 0.25487(11) 0.0191(3) Uani 1 1 d . . . C13 C 1.2004(2) -0.0032(2) 0.36119(11) 0.0196(3) Uani 1 1 d . . . C14 C 1.2633(2) 0.1587(2) 0.43502(11) 0.0211(3) Uani 1 1 d . . . C15 C 1.2948(2) 0.1673(2) 0.53420(12) 0.0259(3) Uani 1 1 d . . . H15 H 1.3339 0.2765 0.5819 0.031 Uiso 1 1 calc R . . C16 C 1.2671(3) 0.0107(2) 0.56142(12) 0.0297(4) Uani 1 1 d . . . H16 H 1.2863 0.0139 0.6281 0.036 Uiso 1 1 calc R . . C17 C 1.2110(3) -0.1506(2) 0.49019(13) 0.0306(4) Uani 1 1 d . . . H17 H 1.1960 -0.2547 0.5089 0.037 Uiso 1 1 calc R . . C18 C 1.1770(2) -0.1577(2) 0.39066(12) 0.0254(3) Uani 1 1 d . . . H18 H 1.1382 -0.2671 0.3432 0.030 Uiso 1 1 calc R . . N1 N 1.30819(19) 0.32974(17) 0.40778(10) 0.0247(3) Uani 1 1 d . . . O1 O 1.03532(15) 0.06560(14) 0.24605(7) 0.0207(2) Uani 1 1 d . . . O2 O 1.18068(16) -0.11407(15) 0.18627(8) 0.0254(3) Uani 1 1 d . . . O3 O 1.38990(17) 0.35456(15) 0.33323(9) 0.0305(3) Uani 1 1 d . . . O4 O 1.2663(2) 0.44112(16) 0.46257(10) 0.0383(3) Uani 1 1 d . . . O5 O 0.70264(17) 0.69385(15) 0.23573(9) 0.0294(3) Uani 1 1 d . . . O6 O 0.46877(16) 0.48748(15) 0.11342(8) 0.0269(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 C1 0.0217(7) 0.0196(7) 0.0178(7) 0.0041(6) 0.0008(6) 0.0093(6) C2 0.0250(8) 0.0198(7) 0.0172(7) 0.0028(6) 0.0011(6) 0.0103(6) C3 0.0189(7) 0.0204(7) 0.0245(8) 0.0067(6) -0.0007(6) 0.0070(6) C4 0.0205(7) 0.0212(7) 0.0188(7) 0.0055(6) 0.0025(6) 0.0103(6) C5 0.0213(7) 0.0178(7) 0.0210(7) 0.0051(6) 0.0024(6) 0.0084(6) C6 0.0208(7) 0.0203(7) 0.0202(7) 0.0022(6) -0.0005(6) 0.0094(6) C7 0.0279(8) 0.0276(8) 0.0167(7) 0.0063(6) 0.0032(6) 0.0158(6) C8 0.0226(8) 0.0234(8) 0.0245(8) 0.0107(6) 0.0049(6) 0.0104(6) C9 0.0254(8) 0.0227(8) 0.0183(7) 0.0035(6) 0.0012(6) 0.0113(6) C10 0.0220(7) 0.0251(8) 0.0188(7) 0.0080(6) 0.0055(6) 0.0114(6) C11 0.0322(9) 0.0383(10) 0.0398(10) 0.0139(8) 0.0050(8) 0.0245(8) C12 0.0180(7) 0.0160(7) 0.0227(7) 0.0039(6) 0.0032(6) 0.0074(5) C13 0.0186(7) 0.0208(7) 0.0210(7) 0.0045(6) 0.0035(6) 0.0104(6) C14 0.0201(7) 0.0202(7) 0.0245(8) 0.0059(6) 0.0033(6) 0.0100(6) C15 0.0293(8) 0.0256(8) 0.0213(8) 0.0018(6) 0.0013(6) 0.0126(6) C16 0.0348(9) 0.0387(10) 0.0218(8) 0.0116(7) 0.0034(7) 0.0199(8) C17 0.0357(9) 0.0295(9) 0.0357(9) 0.0165(7) 0.0078(7) 0.0186(7) C18 0.0303(8) 0.0205(8) 0.0279(8) 0.0040(6) 0.0027(7) 0.0145(6) N1 0.0247(7) 0.0201(7) 0.0256(7) 0.0030(5) -0.0014(5) 0.0079(5) O1 0.0242(5) 0.0229(5) 0.0180(5) 0.0038(4) 0.0017(4) 0.0138(4) O2 0.0294(6) 0.0262(6) 0.0230(6) 0.0016(4) 0.0043(5) 0.0164(5) O3 0.0291(6) 0.0279(6) 0.0310(6) 0.0122(5) 0.0049(5) 0.0070(5) O4 0.0547(8) 0.0249(6) 0.0386(7) 0.0024(5) 0.0062(6) 0.0233(6) O5 0.0338(6) 0.0237(6) 0.0299(6) 0.0032(5) 0.0012(5) 0.0137(5) O6 0.0259(6) 0.0300(6) 0.0290(6) 0.0057(5) -0.0005(5) 0.0170(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 C1 C9 1.487(2) . ? C1 C6 1.563(2) . ? C1 C8 1.567(2) . ? C1 C2 1.568(2) . ? C2 C3 1.564(2) . ? C2 C5 1.564(2) . ? C2 H2 0.9800 . ? C3 C4 1.558(2) . ? C3 C8 1.563(2) . ? C3 H3 0.9800 . ? C4 C10 1.479(2) . ? C4 C7 1.566(2) . ? C4 C5 1.575(2) . ? C5 C6 1.566(2) . ? C5 H5 0.9800 . ? C6 C7 1.561(2) . ? C6 H6 0.9800 . ? C7 C8 1.565(2) . ? C7 H7 0.9800 . ? C8 H8 0.9800 . ? C9 O1 1.4513(18) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 O5 1.2049(18) . ? C10 O6 1.3413(18) . ? C11 O6 1.4468(19) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 O2 1.2038(18) . ? C12 O1 1.3357(17) . ? C12 C13 1.490(2) . ? C13 C18 1.389(2) . ? C13 C14 1.397(2) . ? C14 C15 1.378(2) . ? C14 N1 1.468(2) . ? C15 C16 1.382(2) . ? C15 H15 0.9300 . ? C16 C17 1.381(2) . ? C16 H16 0.9300 . ? C17 C18 1.389(2) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? N1 O3 1.2250(17) . ? N1 O4 1.2255(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 C1 C6 123.36(12) . . ? C9 C1 C8 127.33(13) . . ? C6 C1 C8 90.04(11) . . ? C9 C1 C2 124.80(12) . . ? C6 C1 C2 90.31(11) . . ? C8 C1 C2 90.02(11) . . ? C3 C2 C5 90.17(11) . . ? C3 C2 C1 89.82(11) . . ? C5 C2 C1 89.63(10) . . ? C3 C2 H2 125.4 . . ? C5 C2 H2 125.4 . . ? C1 C2 H2 125.4 . . ? C4 C3 C8 89.54(11) . . ? C4 C3 C2 90.26(11) . . ? C8 C3 C2 90.28(11) . . ? C4 C3 H3 125.2 . . ? C8 C3 H3 125.2 . . ? C2 C3 H3 125.2 . . ? C10 C4 C3 129.13(13) . . ? C10 C4 C7 126.57(13) . . ? C3 C4 C7 90.68(11) . . ? C10 C4 C5 119.51(12) . . ? C3 C4 C5 89.95(11) . . ? C7 C4 C5 89.58(11) . . ? C2 C5 C6 90.33(11) . . ? C2 C5 C4 89.63(11) . . ? C6 C5 C4 89.91(11) . . ? C2 C5 H5 125.3 . . ? C6 C5 H5 125.3 . . ? C4 C5 H5 125.3 . . ? C7 C6 C1 90.02(11) . . ? C7 C6 C5 90.08(11) . . ? C1 C6 C5 89.73(11) . . ? C7 C6 H6 125.3 . . ? C1 C6 H6 125.3 . . ? C5 C6 H6 125.3 . . ? C6 C7 C8 90.17(11) . . ? C6 C7 C4 90.42(11) . . ? C8 C7 C4 89.22(11) . . ? C6 C7 H7 125.3 . . ? C8 C7 H7 125.3 . . ? C4 C7 H7 125.3 . . ? C3 C8 C7 90.55(11) . . ? C3 C8 C1 89.87(11) . . ? C7 C8 C1 89.77(11) . . ? C3 C8 H8 125.2 . . ? C7 C8 H8 125.2 . . ? C1 C8 H8 125.2 . . ? O1 C9 C1 105.78(12) . . ? O1 C9 H9A 110.6 . . ? C1 C9 H9A 110.6 . . ? O1 C9 H9B 110.6 . . ? C1 C9 H9B 110.6 . . ? H9A C9 H9B 108.7 . . ? O5 C10 O6 123.38(14) . . ? O5 C10 C4 124.41(14) . . ? O6 C10 C4 112.08(13) . . ? O6 C11 H11A 109.5 . . ? O6 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? O6 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? O2 C12 O1 124.68(14) . . ? O2 C12 C13 124.24(13) . . ? O1 C12 C13 111.03(12) . . ? C18 C13 C14 117.42(14) . . ? C18 C13 C12 118.03(13) . . ? C14 C13 C12 124.37(13) . . ? C15 C14 C13 122.49(14) . . ? C15 C14 N1 117.42(13) . . ? C13 C14 N1 120.02(13) . . ? C14 C15 C16 118.73(15) . . ? C14 C15 H15 120.6 . . ? C16 C15 H15 120.6 . . ? C17 C16 C15 120.38(15) . . ? C17 C16 H16 119.8 . . ? C15 C16 H16 119.8 . . ? C16 C17 C18 120.21(15) . . ? C16 C17 H17 119.9 . . ? C18 C17 H17 119.9 . . ? C17 C18 C13 120.71(15) . . ? C17 C18 H18 119.6 . . ? C13 C18 H18 119.6 . . ? O3 N1 O4 123.98(14) . . ? O3 N1 C14 118.10(13) . . ? O4 N1 C14 117.89(13) . . ? C12 O1 C9 116.03(11) . . ? C10 O6 C11 114.88(13) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C9 C1 C2 C3 137.48(14) . . . . ? C6 C1 C2 C3 -90.19(11) . . . . ? C8 C1 C2 C3 -0.15(11) . . . . ? C9 C1 C2 C5 -132.36(14) . . . . ? C6 C1 C2 C5 -0.02(11) . . . . ? C8 C1 C2 C5 90.02(11) . . . . ? C5 C2 C3 C4 0.06(11) . . . . ? C1 C2 C3 C4 89.69(10) . . . . ? C5 C2 C3 C8 -89.48(11) . . . . ? C1 C2 C3 C8 0.15(11) . . . . ? C8 C3 C4 C10 -140.42(15) . . . . ? C2 C3 C4 C10 129.30(15) . . . . ? C8 C3 C4 C7 0.64(11) . . . . ? C2 C3 C4 C7 -89.64(11) . . . . ? C8 C3 C4 C5 90.22(11) . . . . ? C2 C3 C4 C5 -0.06(11) . . . . ? C3 C2 C5 C6 89.85(11) . . . . ? C1 C2 C5 C6 0.02(11) . . . . ? C3 C2 C5 C4 -0.06(10) . . . . ? C1 C2 C5 C4 -89.88(11) . . . . ? C10 C4 C5 C2 -136.38(13) . . . . ? C3 C4 C5 C2 0.06(11) . . . . ? C7 C4 C5 C2 90.74(11) . . . . ? C10 C4 C5 C6 133.29(13) . . . . ? C3 C4 C5 C6 -90.27(11) . . . . ? C7 C4 C5 C6 0.41(11) . . . . ? C9 C1 C6 C7 -136.51(14) . . . . ? C8 C1 C6 C7 0.09(11) . . . . ? C2 C1 C6 C7 90.11(11) . . . . ? C9 C1 C6 C5 133.41(14) . . . . ? C8 C1 C6 C5 -90.00(11) . . . . ? C2 C1 C6 C5 0.02(11) . . . . ? C2 C5 C6 C7 -90.04(11) . . . . ? C4 C5 C6 C7 -0.42(11) . . . . ? C2 C5 C6 C1 -0.02(11) . . . . ? C4 C5 C6 C1 89.60(11) . . . . ? C1 C6 C7 C8 -0.09(11) . . . . ? C5 C6 C7 C8 89.64(11) . . . . ? C1 C6 C7 C4 -89.31(11) . . . . ? C5 C6 C7 C4 0.42(11) . . . . ? C10 C4 C7 C6 -127.85(15) . . . . ? C3 C4 C7 C6 89.52(11) . . . . ? C5 C4 C7 C6 -0.42(11) . . . . ? C10 C4 C7 C8 141.99(15) . . . . ? C3 C4 C7 C8 -0.64(11) . . . . ? C5 C4 C7 C8 -90.58(11) . . . . ? C4 C3 C8 C7 -0.64(11) . . . . ? C2 C3 C8 C7 89.62(11) . . . . ? C4 C3 C8 C1 -90.41(11) . . . . ? C2 C3 C8 C1 -0.15(11) . . . . ? C6 C7 C8 C3 -89.78(11) . . . . ? C4 C7 C8 C3 0.64(11) . . . . ? C6 C7 C8 C1 0.09(11) . . . . ? C4 C7 C8 C1 90.51(11) . . . . ? C9 C1 C8 C3 -135.75(15) . . . . ? C6 C1 C8 C3 90.46(11) . . . . ? C2 C1 C8 C3 0.15(11) . . . . ? C9 C1 C8 C7 133.71(15) . . . . ? C6 C1 C8 C7 -0.09(10) . . . . ? C2 C1 C8 C7 -90.40(11) . . . . ? C6 C1 C9 O1 57.37(17) . . . . ? C8 C1 C9 O1 -62.84(18) . . . . ? C2 C1 C9 O1 175.12(12) . . . . ? C3 C4 C10 O5 171.66(15) . . . . ? C7 C4 C10 O5 43.1(2) . . . . ? C5 C4 C10 O5 -71.0(2) . . . . ? C3 C4 C10 O6 -12.3(2) . . . . ? C7 C4 C10 O6 -140.80(14) . . . . ? C5 C4 C10 O6 105.04(15) . . . . ? O2 C12 C13 C18 -43.6(2) . . . . ? O1 C12 C13 C18 134.00(14) . . . . ? O2 C12 C13 C14 141.41(16) . . . . ? O1 C12 C13 C14 -40.97(19) . . . . ? C18 C13 C14 C15 -2.4(2) . . . . ? C12 C13 C14 C15 172.57(14) . . . . ? C18 C13 C14 N1 174.40(13) . . . . ? C12 C13 C14 N1 -10.6(2) . . . . ? C13 C14 C15 C16 1.4(2) . . . . ? N1 C14 C15 C16 -175.53(14) . . . . ? C14 C15 C16 C17 0.7(2) . . . . ? C15 C16 C17 C18 -1.7(3) . . . . ? C16 C17 C18 C13 0.6(3) . . . . ? C14 C13 C18 C17 1.4(2) . . . . ? C12 C13 C18 C17 -173.90(14) . . . . ? C15 C14 N1 O3 139.02(15) . . . . ? C13 C14 N1 O3 -38.0(2) . . . . ? C15 C14 N1 O4 -39.1(2) . . . . ? C13 C14 N1 O4 143.95(15) . . . . ? O2 C12 O1 C9 -4.3(2) . . . . ? C13 C12 O1 C9 178.08(12) . . . . ? C1 C9 O1 C12 -175.59(12) . . . . ? O5 C10 O6 C11 3.7(2) . . . . ? C4 C10 O6 C11 -172.44(13) . . . . ? _diffrn_measured_fraction_theta_max 0.870 _diffrn_reflns_theta_full 50.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.322 _refine_diff_density_min -0.265 _refine_diff_density_rms 0.047 data_shelxl11e _database_code_depnum_ccdc_archive 'CCDC 923689' #TrackingRef 'CMPD_11e.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H11 Cl3 O4' _chemical_formula_weight 337.57 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' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_space_group_name_H-M 'P -1' _symmetry_cell_setting triclinic loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.7385(4) _cell_length_b 10.3221(7) _cell_length_c 13.5698(9) _cell_angle_alpha 111.374(6) _cell_angle_beta 92.266(5) _cell_angle_gamma 102.902(6) _cell_volume 723.10(9) _cell_formula_units_Z 2 _cell_measurement_temperature 130.0(2) _cell_measurement_reflns_used 2869 _cell_measurement_theta_min 3.5262 _cell_measurement_theta_max 73.0306 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.3520 _exptl_crystal_size_mid 0.2489 _exptl_crystal_size_min 0.2000 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.550 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 344 _exptl_absorpt_coefficient_mu 5.839 _exptl_absorpt_correction_T_min 0.293 _exptl_absorpt_correction_T_max 0.497 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) Numerical absorption correction based on gaussian integration over a multifaceted crystal model ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 130.0(2) _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'Enhance (Cu) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Sapphire3' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4069 _diffrn_reflns_av_R_equivalents 0.0265 _diffrn_reflns_av_sigmaI/netI 0.0253 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.53 _diffrn_reflns_theta_max 67.49 _reflns_number_total 2563 _reflns_number_gt 2200 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0831P)^2^+0.4177P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0100(15) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2563 _refine_ls_number_parameters 202 _refine_ls_number_restraints 22 _refine_ls_R_factor_all 0.0578 _refine_ls_R_factor_gt 0.0522 _refine_ls_wR_factor_ref 0.1479 _refine_ls_wR_factor_gt 0.1436 _refine_ls_goodness_of_fit_ref 1.079 _refine_ls_restrained_S_all 1.115 _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 Cl2' Cl 0.5990(15) 0.6996(11) 0.2997(12) 0.117(3) Uani 0.42(2) 1 d PDU A 2 Cl3' Cl 0.363(4) 0.6103(13) 0.4584(6) 0.117(3) Uani 0.42(2) 1 d PDU A 2 Cl1 Cl 0.09455(17) 0.53341(8) 0.26495(8) 0.0693(3) Uani 1 1 d D A 1 Cl2 Cl 0.5630(10) 0.6840(7) 0.2740(6) 0.0732(13) Uani 0.58(2) 1 d PDU A 1 Cl3 Cl 0.452(2) 0.6283(10) 0.4562(5) 0.117(3) Uani 0.58(2) 1 d PDU A 1 O1 O 0.2167(4) 0.85869(19) 0.32679(14) 0.0427(5) Uani 1 1 d . . . C1 C 0.2162(5) 1.0632(3) 0.2846(2) 0.0342(6) Uani 1 1 d . . . O2 O 0.6556(4) 1.3026(3) 0.07734(19) 0.0528(6) Uani 1 1 d . . . O3 O 0.2838(4) 1.2961(3) 0.01920(19) 0.0560(6) Uani 1 1 d . . . C7 C 0.3835(5) 1.0472(3) 0.1389(2) 0.0399(6) Uani 1 1 d . . . H7 H 0.4576 0.9871 0.0817 0.048 Uiso 1 1 calc R . . C2 C 0.1807(5) 1.2140(3) 0.2965(2) 0.0413(6) Uani 1 1 d . . . H2 H 0.1074 1.2743 0.3539 0.050 Uiso 1 1 calc R . . C10 C 0.4188(5) 1.2714(3) 0.0758(2) 0.0345(6) Uani 1 1 d . . . C8 C 0.4794(5) 1.1086(3) 0.2603(2) 0.0366(6) Uani 1 1 d . . . H8 H 0.6224 1.0926 0.2913 0.044 Uiso 1 1 calc R . . C6 C 0.1211(5) 1.0028(3) 0.1627(2) 0.0432(7) Uani 1 1 d . . . H6 H 0.0048 0.9101 0.1232 0.052 Uiso 1 1 calc R . . C4 C 0.3450(5) 1.1978(3) 0.1501(2) 0.0342(6) Uani 1 1 d . . . C9 C 0.1447(6) 0.9952(3) 0.3618(2) 0.0407(6) Uani 1 1 d . . . H9A H 0.2249 1.0579 0.4330 0.049 Uiso 1 1 calc R . . H9B H -0.0282 0.9772 0.3630 0.049 Uiso 1 1 calc R . . C3 C 0.4420(5) 1.2581(3) 0.2721(2) 0.0359(6) Uani 1 1 d . . . H3 H 0.5584 1.3507 0.3114 0.043 Uiso 1 1 calc R . . C12 C 0.2525(6) 0.8107(3) 0.4006(2) 0.0418(6) Uani 1 1 d . A . C5 C 0.0842(5) 1.1535(3) 0.1749(3) 0.0435(7) Uani 1 1 d . . . H5 H -0.0588 1.1698 0.1442 0.052 Uiso 1 1 calc R . . O4 O 0.2322(7) 0.8638(3) 0.49223(19) 0.0855(10) Uani 1 1 d . . . C11 C 0.7460(7) 1.3686(5) 0.0038(3) 0.0664(10) Uani 1 1 d . . . H11A H 0.9181 1.3842 0.0088 0.100 Uiso 1 1 calc R . . H11B H 0.7053 1.4590 0.0217 0.100 Uiso 1 1 calc R . . H11C H 0.6744 1.3061 -0.0678 0.100 Uiso 1 1 calc R . . C13 C 0.3320(4) 0.6688(3) 0.35404(18) 0.0490(7) Uani 1 1 d 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 Cl2' 0.0419(19) 0.071(2) 0.191(7) -0.008(4) -0.003(3) 0.0257(16) Cl3' 0.270(10) 0.065(3) 0.043(2) 0.026(2) 0.000(4) 0.088(5) Cl1 0.0658(6) 0.0372(4) 0.0907(7) 0.0111(4) -0.0050(4) 0.0111(4) Cl2 0.0516(18) 0.0612(18) 0.110(3) 0.0263(18) 0.0309(19) 0.0282(14) Cl3 0.218(6) 0.067(2) 0.065(2) 0.0035(14) -0.047(3) 0.084(3) O1 0.0688(13) 0.0302(9) 0.0391(10) 0.0173(8) 0.0147(9) 0.0239(9) C1 0.0406(14) 0.0262(12) 0.0417(13) 0.0169(10) 0.0093(10) 0.0125(10) O2 0.0405(11) 0.0689(14) 0.0744(14) 0.0549(12) 0.0109(10) 0.0161(10) O3 0.0470(12) 0.0706(15) 0.0656(13) 0.0471(12) -0.0023(10) 0.0103(10) C7 0.0599(17) 0.0289(13) 0.0359(13) 0.0148(10) 0.0119(12) 0.0162(12) C2 0.0518(16) 0.0310(13) 0.0536(16) 0.0230(12) 0.0210(13) 0.0207(12) C10 0.0411(14) 0.0282(12) 0.0356(12) 0.0149(10) 0.0007(10) 0.0082(10) C8 0.0388(14) 0.0386(14) 0.0419(14) 0.0228(11) 0.0073(11) 0.0156(11) C6 0.0508(16) 0.0300(13) 0.0465(15) 0.0186(11) -0.0021(12) 0.0004(11) C4 0.0394(14) 0.0284(12) 0.0380(13) 0.0166(10) 0.0019(10) 0.0088(10) C9 0.0562(17) 0.0304(13) 0.0472(15) 0.0206(11) 0.0194(13) 0.0214(12) C3 0.0430(14) 0.0285(12) 0.0345(12) 0.0128(10) 0.0026(10) 0.0051(10) C12 0.0599(18) 0.0342(14) 0.0384(14) 0.0166(11) 0.0084(12) 0.0207(12) C5 0.0361(14) 0.0416(15) 0.0623(17) 0.0326(13) 0.0021(12) 0.0076(11) O4 0.170(3) 0.0757(18) 0.0458(14) 0.0321(12) 0.0378(16) 0.080(2) C11 0.0539(19) 0.088(3) 0.095(3) 0.072(2) 0.0260(18) 0.0241(18) C13 0.070(2) 0.0352(15) 0.0447(15) 0.0130(12) -0.0039(14) 0.0248(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 Cl2' C13 1.742(4) . ? Cl3' C13 1.748(3) . ? Cl1 C13 1.749(2) . ? Cl2 C13 1.763(3) . ? Cl3 C13 1.746(3) . ? O1 C12 1.297(3) . ? O1 C9 1.472(3) . ? C1 C9 1.483(4) . ? C1 C8 1.564(4) . ? C1 C6 1.564(4) . ? C1 C2 1.567(3) . ? O2 C10 1.322(3) . ? O2 C11 1.452(4) . ? O3 C10 1.200(3) . ? C7 C6 1.556(4) . ? C7 C8 1.558(4) . ? C7 C4 1.573(3) . ? C2 C3 1.552(4) . ? C2 C5 1.562(4) . ? C10 C4 1.490(3) . ? C8 C3 1.557(3) . ? C6 C5 1.567(4) . ? C4 C5 1.552(4) . ? C4 C3 1.567(3) . ? C12 O4 1.185(4) . ? C12 C13 1.548(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 C12 O1 C9 115.9(2) . . ? C9 C1 C8 125.5(2) . . ? C9 C1 C6 127.2(2) . . ? C8 C1 C6 90.1(2) . . ? C9 C1 C2 123.2(2) . . ? C8 C1 C2 89.71(19) . . ? C6 C1 C2 90.0(2) . . ? C10 O2 C11 115.5(2) . . ? C6 C7 C8 90.6(2) . . ? C6 C7 C4 89.4(2) . . ? C8 C7 C4 90.06(19) . . ? C3 C2 C5 90.3(2) . . ? C3 C2 C1 89.92(19) . . ? C5 C2 C1 90.0(2) . . ? O3 C10 O2 123.6(2) . . ? O3 C10 C4 125.4(3) . . ? O2 C10 C4 111.0(2) . . ? C3 C8 C7 90.26(19) . . ? C3 C8 C1 89.86(18) . . ? C7 C8 C1 89.6(2) . . ? C7 C6 C1 89.7(2) . . ? C7 C6 C5 90.41(19) . . ? C1 C6 C5 89.9(2) . . ? C10 C4 C5 125.7(2) . . ? C10 C4 C3 125.3(2) . . ? C5 C4 C3 90.2(2) . . ? C10 C4 C7 124.9(2) . . ? C5 C4 C7 90.35(19) . . ? C3 C4 C7 89.35(19) . . ? O1 C9 C1 107.3(2) . . ? C2 C3 C8 90.51(19) . . ? C2 C3 C4 89.6(2) . . ? C8 C3 C4 90.33(18) . . ? O4 C12 O1 127.3(3) . . ? O4 C12 C13 121.9(2) . . ? O1 C12 C13 110.8(2) . . ? C4 C5 C2 89.8(2) . . ? C4 C5 C6 89.8(2) . . ? C2 C5 C6 90.1(2) . . ? C12 C13 Cl2' 109.5(4) . . ? C12 C13 Cl3 110.7(3) . . ? Cl2' C13 Cl3 96.4(5) . . ? C12 C13 Cl3' 106.9(4) . . ? Cl2' C13 Cl3' 112.7(6) . . ? Cl3 C13 Cl3' 16.9(7) . . ? C12 C13 Cl1 109.56(18) . . ? Cl2' C13 Cl1 114.6(5) . . ? Cl3 C13 Cl1 115.5(4) . . ? Cl3' C13 Cl1 103.2(6) . . ? C12 C13 Cl2 111.2(2) . . ? Cl2' C13 Cl2 11.7(5) . . ? Cl3 C13 Cl2 105.9(4) . . ? Cl3' C13 Cl2 121.5(6) . . ? Cl1 C13 Cl2 103.7(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C9 C1 C2 C3 133.7(3) . . . . ? C8 C1 C2 C3 0.09(19) . . . . ? C6 C1 C2 C3 -90.0(2) . . . . ? C9 C1 C2 C5 -135.9(3) . . . . ? C8 C1 C2 C5 90.4(2) . . . . ? C6 C1 C2 C5 0.3(2) . . . . ? C11 O2 C10 O3 -0.7(4) . . . . ? C11 O2 C10 C4 177.2(3) . . . . ? C6 C7 C8 C3 -89.48(19) . . . . ? C4 C7 C8 C3 0.0(2) . . . . ? C6 C7 C8 C1 0.38(19) . . . . ? C4 C7 C8 C1 89.81(19) . . . . ? C9 C1 C8 C3 -132.1(2) . . . . ? C6 C1 C8 C3 89.89(19) . . . . ? C2 C1 C8 C3 -0.09(19) . . . . ? C9 C1 C8 C7 137.7(2) . . . . ? C6 C1 C8 C7 -0.38(19) . . . . ? C2 C1 C8 C7 -90.4(2) . . . . ? C8 C7 C6 C1 -0.38(19) . . . . ? C4 C7 C6 C1 -90.43(19) . . . . ? C8 C7 C6 C5 89.6(2) . . . . ? C4 C7 C6 C5 -0.5(2) . . . . ? C9 C1 C6 C7 -136.5(3) . . . . ? C8 C1 C6 C7 0.38(19) . . . . ? C2 C1 C6 C7 90.1(2) . . . . ? C9 C1 C6 C5 133.1(3) . . . . ? C8 C1 C6 C5 -90.04(19) . . . . ? C2 C1 C6 C5 -0.3(2) . . . . ? O3 C10 C4 C5 -6.1(4) . . . . ? O2 C10 C4 C5 176.0(2) . . . . ? O3 C10 C4 C3 -126.9(3) . . . . ? O2 C10 C4 C3 55.2(3) . . . . ? O3 C10 C4 C7 114.6(3) . . . . ? O2 C10 C4 C7 -63.2(3) . . . . ? C6 C7 C4 C10 -135.2(3) . . . . ? C8 C7 C4 C10 134.2(3) . . . . ? C6 C7 C4 C5 0.5(2) . . . . ? C8 C7 C4 C5 -90.1(2) . . . . ? C6 C7 C4 C3 90.7(2) . . . . ? C8 C7 C4 C3 0.0(2) . . . . ? C12 O1 C9 C1 155.4(3) . . . . ? C8 C1 C9 O1 -60.0(3) . . . . ? C6 C1 C9 O1 62.9(4) . . . . ? C2 C1 C9 O1 -177.3(2) . . . . ? C5 C2 C3 C8 -90.12(19) . . . . ? C1 C2 C3 C8 -0.09(19) . . . . ? C5 C2 C3 C4 0.20(19) . . . . ? C1 C2 C3 C4 90.24(19) . . . . ? C7 C8 C3 C2 89.7(2) . . . . ? C1 C8 C3 C2 0.09(19) . . . . ? C7 C8 C3 C4 0.0(2) . . . . ? C1 C8 C3 C4 -89.5(2) . . . . ? C10 C4 C3 C2 135.6(3) . . . . ? C5 C4 C3 C2 -0.21(19) . . . . ? C7 C4 C3 C2 -90.55(19) . . . . ? C10 C4 C3 C8 -133.9(3) . . . . ? C5 C4 C3 C8 90.30(19) . . . . ? C7 C4 C3 C8 0.0(2) . . . . ? C9 O1 C12 O4 0.6(5) . . . . ? C9 O1 C12 C13 -178.8(2) . . . . ? C10 C4 C5 C2 -135.3(2) . . . . ? C3 C4 C5 C2 0.20(19) . . . . ? C7 C4 C5 C2 89.55(19) . . . . ? C10 C4 C5 C6 134.7(3) . . . . ? C3 C4 C5 C6 -89.8(2) . . . . ? C7 C4 C5 C6 -0.5(2) . . . . ? C3 C2 C5 C4 -0.21(19) . . . . ? C1 C2 C5 C4 -90.13(19) . . . . ? C3 C2 C5 C6 89.6(2) . . . . ? C1 C2 C5 C6 -0.3(2) . . . . ? C7 C6 C5 C4 0.5(2) . . . . ? C1 C6 C5 C4 90.2(2) . . . . ? C7 C6 C5 C2 -89.3(2) . . . . ? C1 C6 C5 C2 0.3(2) . . . . ? O4 C12 C13 Cl2' -119.4(6) . . . . ? O1 C12 C13 Cl2' 60.0(6) . . . . ? O4 C12 C13 Cl3 -14.4(6) . . . . ? O1 C12 C13 Cl3 165.0(5) . . . . ? O4 C12 C13 Cl3' 2.9(8) . . . . ? O1 C12 C13 Cl3' -177.6(7) . . . . ? O4 C12 C13 Cl1 114.1(4) . . . . ? O1 C12 C13 Cl1 -66.4(3) . . . . ? O4 C12 C13 Cl2 -131.8(4) . . . . ? O1 C12 C13 Cl2 47.6(4) . . . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 67.49 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.617 _refine_diff_density_min -0.429 _refine_diff_density_rms 0.062 data_shelxl11f _database_code_depnum_ccdc_archive 'CCDC 923690' #TrackingRef 'CMPD_11f.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H14 O5 S' _chemical_formula_weight 270.29 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' _symmetry_space_group_name_H-M 'P -1' _symmetry_cell_setting triclinic loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.8663(3) _cell_length_b 8.9585(6) _cell_length_c 12.2036(7) _cell_angle_alpha 95.715(5) _cell_angle_beta 103.005(5) _cell_angle_gamma 104.096(5) _cell_volume 597.93(6) _cell_formula_units_Z 2 _cell_measurement_temperature 130.0 _cell_measurement_reflns_used 2866 _cell_measurement_theta_min 3.1577 _cell_measurement_theta_max 29.1197 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.6003 _exptl_crystal_size_mid 0.4715 _exptl_crystal_size_min 0.3400 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.501 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 284 _exptl_absorpt_coefficient_mu 0.281 _exptl_absorpt_correction_T_min 0.68733 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.39 (release 18-08-2010 CrysAlis171 .NET) (compiled Aug 18 2010,17:42:00) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 130.0 _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'SuperNova (Mo) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4741 _diffrn_reflns_av_R_equivalents 0.0185 _diffrn_reflns_av_sigmaI/netI 0.0341 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.16 _diffrn_reflns_theta_max 29.18 _reflns_number_total 2777 _reflns_number_gt 2409 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.39 (release 18-08-2010 CrysAlis171 .NET) (compiled Aug 18 2010,17:42:00) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.39 (release 18-08-2010 CrysAlis171 .NET) (compiled Aug 18 2010,17:42:00) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.39 (release 18-08-2010 CrysAlis171 .NET) (compiled Aug 18 2010,17:42:00) ; _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0407P)^2^+0.2556P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.012(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2777 _refine_ls_number_parameters 164 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0447 _refine_ls_R_factor_gt 0.0372 _refine_ls_wR_factor_ref 0.0957 _refine_ls_wR_factor_gt 0.0897 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _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 0.2528(3) 0.52689(18) 0.70958(13) 0.0187(3) Uani 1 1 d . . . C2 C 0.0513(3) 0.60058(19) 0.73616(13) 0.0222(3) Uani 1 1 d . . . H2 H -0.1040 0.5932 0.6822 0.027 Uiso 1 1 calc R . . C3 C 0.0801(3) 0.53937(18) 0.85221(14) 0.0215(3) Uani 1 1 d . . . H3 H -0.0542 0.4877 0.8826 0.026 Uiso 1 1 calc R . . C4 C 0.2811(3) 0.69390(18) 0.91193(13) 0.0182(3) Uani 1 1 d . . . C5 C 0.2492(3) 0.75499(19) 0.79440(14) 0.0242(4) Uani 1 1 d . . . H5 H 0.2374 0.8599 0.7831 0.029 Uiso 1 1 calc R . . C6 C 0.4522(3) 0.68194(19) 0.76859(14) 0.0263(4) Uani 1 1 d . . . H6 H 0.5862 0.7337 0.7380 0.032 Uiso 1 1 calc R . . C7 C 0.4818(3) 0.6207(2) 0.88462(14) 0.0251(4) Uani 1 1 d . . . H7 H 0.6374 0.6278 0.9383 0.030 Uiso 1 1 calc R . . C8 C 0.2824(3) 0.46586(19) 0.82614(13) 0.0221(3) Uani 1 1 d . . . H8 H 0.2938 0.3608 0.8374 0.027 Uiso 1 1 calc R . . C9 C 0.2327(3) 0.43408(19) 0.59848(14) 0.0223(3) Uani 1 1 d . . . H9A H 0.0864 0.3475 0.5777 0.027 Uiso 1 1 calc R . . H9B H 0.2256 0.4986 0.5392 0.027 Uiso 1 1 calc R . . C10 C 0.3035(3) 0.79319(17) 1.02006(13) 0.0182(3) Uani 1 1 d . . . C11 C 0.0973(3) 0.9170(2) 1.12923(16) 0.0312(4) Uani 1 1 d . . . H11A H -0.0640 0.9241 1.1278 0.047 Uiso 1 1 calc R . . H11B H 0.2004 1.0187 1.1303 0.047 Uiso 1 1 calc R . . H11C H 0.1605 0.8769 1.1962 0.047 Uiso 1 1 calc R . . C12 C 0.2752(3) 0.08303(19) 0.62722(14) 0.0244(4) Uani 1 1 d . . . H12A H 0.1113 0.0899 0.6177 0.037 Uiso 1 1 calc R . . H12B H 0.3609 0.1122 0.7064 0.037 Uiso 1 1 calc R . . H12C H 0.2730 -0.0221 0.6011 0.037 Uiso 1 1 calc R . . O1 O 0.4509(2) 0.37583(13) 0.61218(10) 0.0240(3) Uani 1 1 d . . . O2 O 0.6652(2) 0.19850(14) 0.56233(12) 0.0341(3) Uani 1 1 d . . . O3 O 0.2671(2) 0.18624(14) 0.43560(10) 0.0292(3) Uani 1 1 d . . . O4 O 0.4915(2) 0.85286(15) 1.09209(10) 0.0295(3) Uani 1 1 d . . . O5 O 0.0897(2) 0.81357(14) 1.02895(10) 0.0249(3) Uani 1 1 d . . . S1 S 0.42131(7) 0.20866(4) 0.54821(3) 0.02094(13) 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 0.0203(8) 0.0186(7) 0.0168(7) 0.0022(6) 0.0054(6) 0.0042(6) C2 0.0220(8) 0.0260(8) 0.0175(8) -0.0003(6) 0.0002(6) 0.0106(6) C3 0.0222(8) 0.0190(8) 0.0225(8) 0.0015(6) 0.0090(7) 0.0018(6) C4 0.0171(7) 0.0205(7) 0.0164(7) 0.0025(6) 0.0037(6) 0.0045(6) C5 0.0383(10) 0.0173(8) 0.0196(8) 0.0053(6) 0.0109(7) 0.0082(7) C6 0.0274(9) 0.0225(8) 0.0251(8) -0.0035(7) 0.0138(7) -0.0039(7) C7 0.0184(8) 0.0350(9) 0.0203(8) -0.0041(7) 0.0016(7) 0.0109(7) C8 0.0307(9) 0.0205(8) 0.0189(8) 0.0050(6) 0.0082(7) 0.0116(7) C9 0.0200(8) 0.0234(8) 0.0224(8) 0.0005(6) 0.0039(6) 0.0065(6) C10 0.0189(7) 0.0178(7) 0.0188(7) 0.0041(6) 0.0054(6) 0.0057(6) C11 0.0254(9) 0.0324(10) 0.0337(10) -0.0090(8) 0.0102(8) 0.0072(7) C12 0.0291(9) 0.0231(8) 0.0178(8) 0.0046(6) 0.0064(7) 0.0006(7) O1 0.0190(6) 0.0192(6) 0.0317(6) -0.0035(5) 0.0082(5) 0.0027(4) O2 0.0245(6) 0.0276(7) 0.0517(8) -0.0015(6) 0.0173(6) 0.0063(5) O3 0.0427(7) 0.0265(6) 0.0180(6) 0.0023(5) 0.0112(5) 0.0064(5) O4 0.0200(6) 0.0407(7) 0.0231(6) -0.0071(5) -0.0003(5) 0.0100(5) O5 0.0174(6) 0.0283(6) 0.0260(6) -0.0061(5) 0.0053(5) 0.0055(5) S1 0.0222(2) 0.0183(2) 0.0229(2) 0.00098(15) 0.01082(17) 0.00299(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 C1 C9 1.483(2) . ? C1 C8 1.563(2) . ? C1 C6 1.564(2) . ? C1 C2 1.565(2) . ? C2 C5 1.555(2) . ? C2 C3 1.558(2) . ? C3 C8 1.566(2) . ? C3 C4 1.567(2) . ? C4 C10 1.477(2) . ? C4 C7 1.561(2) . ? C4 C5 1.574(2) . ? C5 C6 1.566(2) . ? C6 C7 1.558(2) . ? C7 C8 1.562(2) . ? C9 O1 1.4782(18) . ? C10 O4 1.2073(19) . ? C10 O5 1.3372(18) . ? C11 O5 1.445(2) . ? C12 S1 1.7464(17) . ? O1 S1 1.5691(11) . ? O2 S1 1.4286(12) . ? O3 S1 1.4298(12) . ? 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 C1 C8 125.33(13) . . ? C9 C1 C6 126.18(14) . . ? C8 C1 C6 89.88(12) . . ? C9 C1 C2 124.25(13) . . ? C8 C1 C2 90.01(12) . . ? C6 C1 C2 90.15(12) . . ? C5 C2 C3 90.27(12) . . ? C5 C2 C1 89.90(12) . . ? C3 C2 C1 90.04(11) . . ? C2 C3 C8 90.14(12) . . ? C2 C3 C4 90.32(12) . . ? C8 C3 C4 89.38(12) . . ? C10 C4 C7 125.13(13) . . ? C10 C4 C3 128.18(14) . . ? C7 C4 C3 90.42(12) . . ? C10 C4 C5 122.66(13) . . ? C7 C4 C5 89.93(12) . . ? C3 C4 C5 89.23(12) . . ? C2 C5 C6 90.45(12) . . ? C2 C5 C4 90.18(12) . . ? C6 C5 C4 89.47(12) . . ? C7 C6 C1 90.02(12) . . ? C7 C6 C5 90.33(12) . . ? C1 C6 C5 89.50(12) . . ? C6 C7 C4 90.27(12) . . ? C6 C7 C8 90.17(12) . . ? C4 C7 C8 89.77(12) . . ? C7 C8 C1 89.93(12) . . ? C7 C8 C3 90.42(12) . . ? C1 C8 C3 89.81(11) . . ? O1 C9 C1 106.94(12) . . ? O4 C10 O5 122.90(14) . . ? O4 C10 C4 125.01(14) . . ? O5 C10 C4 112.07(13) . . ? C9 O1 S1 118.02(10) . . ? C10 O5 C11 115.75(12) . . ? O2 S1 O3 119.12(8) . . ? O2 S1 O1 104.17(7) . . ? O3 S1 O1 109.78(7) . . ? O2 S1 C12 109.53(8) . . ? O3 S1 C12 109.10(8) . . ? O1 S1 C12 104.03(7) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C9 C1 C2 C5 -135.50(16) . . . . ? C8 C1 C2 C5 90.10(12) . . . . ? C6 C1 C2 C5 0.22(12) . . . . ? C9 C1 C2 C3 134.24(16) . . . . ? C8 C1 C2 C3 -0.16(12) . . . . ? C6 C1 C2 C3 -90.04(12) . . . . ? C5 C2 C3 C8 -89.74(12) . . . . ? C1 C2 C3 C8 0.16(12) . . . . ? C5 C2 C3 C4 -0.35(12) . . . . ? C1 C2 C3 C4 89.55(12) . . . . ? C2 C3 C4 C10 132.89(15) . . . . ? C8 C3 C4 C10 -136.98(15) . . . . ? C2 C3 C4 C7 -89.58(12) . . . . ? C8 C3 C4 C7 0.56(12) . . . . ? C2 C3 C4 C5 0.35(12) . . . . ? C8 C3 C4 C5 90.48(12) . . . . ? C3 C2 C5 C6 89.82(12) . . . . ? C1 C2 C5 C6 -0.22(12) . . . . ? C3 C2 C5 C4 0.35(12) . . . . ? C1 C2 C5 C4 -89.69(12) . . . . ? C10 C4 C5 C2 -136.87(15) . . . . ? C7 C4 C5 C2 90.07(12) . . . . ? C3 C4 C5 C2 -0.35(12) . . . . ? C10 C4 C5 C6 132.68(15) . . . . ? C7 C4 C5 C6 -0.37(12) . . . . ? C3 C4 C5 C6 -90.79(12) . . . . ? C9 C1 C6 C7 -135.54(15) . . . . ? C8 C1 C6 C7 0.10(12) . . . . ? C2 C1 C6 C7 90.11(12) . . . . ? C9 C1 C6 C5 134.14(15) . . . . ? C8 C1 C6 C5 -90.22(12) . . . . ? C2 C1 C6 C5 -0.22(12) . . . . ? C2 C5 C6 C7 -89.80(12) . . . . ? C4 C5 C6 C7 0.37(12) . . . . ? C2 C5 C6 C1 0.22(12) . . . . ? C4 C5 C6 C1 90.39(12) . . . . ? C1 C6 C7 C4 -89.88(12) . . . . ? C5 C6 C7 C4 -0.38(12) . . . . ? C1 C6 C7 C8 -0.10(12) . . . . ? C5 C6 C7 C8 89.40(12) . . . . ? C10 C4 C7 C6 -130.85(16) . . . . ? C3 C4 C7 C6 89.61(12) . . . . ? C5 C4 C7 C6 0.37(12) . . . . ? C10 C4 C7 C8 138.98(15) . . . . ? C3 C4 C7 C8 -0.56(12) . . . . ? C5 C4 C7 C8 -89.79(12) . . . . ? C6 C7 C8 C1 0.10(12) . . . . ? C4 C7 C8 C1 90.37(12) . . . . ? C6 C7 C8 C3 -89.71(12) . . . . ? C4 C7 C8 C3 0.56(12) . . . . ? C9 C1 C8 C7 136.13(15) . . . . ? C6 C1 C8 C7 -0.10(12) . . . . ? C2 C1 C8 C7 -90.25(12) . . . . ? C9 C1 C8 C3 -133.46(15) . . . . ? C6 C1 C8 C3 90.31(12) . . . . ? C2 C1 C8 C3 0.16(12) . . . . ? C2 C3 C8 C7 89.76(12) . . . . ? C4 C3 C8 C7 -0.56(12) . . . . ? C2 C3 C8 C1 -0.16(12) . . . . ? C4 C3 C8 C1 -90.48(12) . . . . ? C8 C1 C9 O1 -56.5(2) . . . . ? C6 C1 C9 O1 64.48(19) . . . . ? C2 C1 C9 O1 -175.40(13) . . . . ? C7 C4 C10 O4 14.0(3) . . . . ? C3 C4 C10 O4 138.40(17) . . . . ? C5 C4 C10 O4 -102.67(19) . . . . ? C7 C4 C10 O5 -167.45(14) . . . . ? C3 C4 C10 O5 -43.1(2) . . . . ? C5 C4 C10 O5 75.86(19) . . . . ? C1 C9 O1 S1 143.86(11) . . . . ? O4 C10 O5 C11 2.1(2) . . . . ? C4 C10 O5 C11 -176.44(14) . . . . ? C9 O1 S1 O2 170.40(12) . . . . ? C9 O1 S1 O3 41.78(13) . . . . ? C9 O1 S1 C12 -74.85(13) . . . . ? _diffrn_measured_fraction_theta_max 0.861 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.347 _refine_diff_density_min -0.342 _refine_diff_density_rms 0.054 data_shelxl15 _database_code_depnum_ccdc_archive 'CCDC 923691' #TrackingRef 'CMPD_15.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H15 N O7 S' _chemical_formula_weight 377.36 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' _symmetry_space_group_name_H-M 'P 1 21 1' _symmetry_cell_setting monoclinic loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.3222(2) _cell_length_b 8.3972(3) _cell_length_c 13.2244(4) _cell_angle_alpha 90.00 _cell_angle_beta 92.244(3) _cell_angle_gamma 90.00 _cell_volume 812.49(4) _cell_formula_units_Z 2 _cell_measurement_temperature 130.0 _cell_measurement_reflns_used 2785 _cell_measurement_theta_min 2.8683 _cell_measurement_theta_max 29.1124 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.6400 _exptl_crystal_size_mid 0.4960 _exptl_crystal_size_min 0.1100 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.542 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 392 _exptl_absorpt_coefficient_mu 0.242 _exptl_absorpt_correction_T_min 0.46980 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.39 (release 18-08-2010 CrysAlis171 .NET) (compiled Aug 18 2010,17:42:00) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 130.0 _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'SuperNova (Mo) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5025 _diffrn_reflns_av_R_equivalents 0.0234 _diffrn_reflns_av_sigmaI/netI 0.0400 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.87 _diffrn_reflns_theta_max 29.18 _reflns_number_total 3062 _reflns_number_gt 2810 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.39 (release 18-08-2010 CrysAlis171 .NET) (compiled Aug 18 2010,17:42:00) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.39 (release 18-08-2010 CrysAlis171 .NET) (compiled Aug 18 2010,17:42:00) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.39 (release 18-08-2010 CrysAlis171 .NET) (compiled Aug 18 2010,17:42:00) ; _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0525P)^2^+0.1848P] 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 0.06(8) _refine_ls_number_reflns 3062 _refine_ls_number_parameters 235 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0428 _refine_ls_R_factor_gt 0.0375 _refine_ls_wR_factor_ref 0.0936 _refine_ls_wR_factor_gt 0.0894 _refine_ls_goodness_of_fit_ref 1.004 _refine_ls_restrained_S_all 1.004 _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 1.0157(3) 1.0931(3) 0.69062(17) 0.0230(5) Uani 1 1 d . . . C2 C 1.0562(3) 0.8435(4) 0.63538(19) 0.0309(7) Uani 1 1 d . . . H2 H 1.1188 0.7479 0.6122 0.037 Uiso 1 1 calc R . . C3 C 0.9216(3) 0.8232(3) 0.72293(17) 0.0253(5) Uani 1 1 d . . . H3 H 0.9324 0.7335 0.7702 0.030 Uiso 1 1 calc R . . C4 C 0.7532(3) 0.8414(3) 0.64903(16) 0.0232(6) Uani 1 1 d . . . C5 C 0.8903(3) 0.9054(4) 0.56880(19) 0.0279(6) Uani 1 1 d . . . H5 H 0.8756 0.8783 0.4969 0.034 Uiso 1 1 calc R . . C6 C 0.8623(3) 1.0781(3) 0.60733(17) 0.0255(5) Uani 1 1 d . . . H6 H 0.8316 1.1660 0.5609 0.031 Uiso 1 1 calc R . . C7 C 0.7243(3) 1.0162(3) 0.68585(18) 0.0237(5) Uani 1 1 d . . . H7 H 0.6071 1.0653 0.7010 0.028 Uiso 1 1 calc R . . C8 C 0.8932(3) 0.9971(3) 0.76134(18) 0.0226(5) Uani 1 1 d . . . H8 H 0.8864 1.0221 0.8335 0.027 Uiso 1 1 calc R . . C9 C 1.1734(3) 0.9887(4) 0.6605(2) 0.0330(6) Uani 1 1 d . . . H9A H 1.2612 0.9698 0.7160 0.040 Uiso 1 1 calc R . . H9B H 1.2348 1.0297 0.6022 0.040 Uiso 1 1 calc R . . C10 C 0.6099(3) 0.7232(3) 0.62366(17) 0.0246(5) Uani 1 1 d . . . C11 C 0.5332(4) 0.4511(4) 0.6212(2) 0.0406(7) Uani 1 1 d . . . H11A H 0.5836 0.3494 0.6400 0.061 Uiso 1 1 calc R . . H11B H 0.5052 0.4528 0.5496 0.061 Uiso 1 1 calc R . . H11C H 0.4235 0.4692 0.6569 0.061 Uiso 1 1 calc R . . C12 C 0.9488(3) 1.3294(3) 0.89562(16) 0.0220(5) Uani 1 1 d . . . C13 C 0.7998(3) 1.4160(3) 0.85765(18) 0.0242(5) Uani 1 1 d . . . H13 H 0.8018 1.4620 0.7937 0.029 Uiso 1 1 calc R . . C14 C 0.6484(3) 1.4329(3) 0.91599(18) 0.0249(5) Uani 1 1 d . . . H14 H 0.5466 1.4900 0.8924 0.030 Uiso 1 1 calc R . . C15 C 0.6531(3) 1.3625(3) 1.01020(17) 0.0233(5) Uani 1 1 d . . . C16 C 0.7997(3) 1.2763(3) 1.04894(17) 0.0270(6) Uani 1 1 d . . . H16 H 0.7970 1.2302 1.1128 0.032 Uiso 1 1 calc R . . C17 C 0.9511(3) 1.2597(3) 0.99043(18) 0.0259(5) Uani 1 1 d . . . H17 H 1.0527 1.2028 1.0144 0.031 Uiso 1 1 calc R . . N1 N 0.4897(3) 1.3776(3) 1.07207(16) 0.0296(5) Uani 1 1 d . . . O1 O 1.0561(2) 1.2594(2) 0.71321(12) 0.0257(4) Uani 1 1 d . . . O2 O 0.6649(3) 0.5751(2) 0.64671(14) 0.0338(5) Uani 1 1 d . . . O3 O 0.4636(2) 0.7530(3) 0.58438(15) 0.0359(5) Uani 1 1 d . . . O4 O 1.2115(2) 1.4674(2) 0.80193(15) 0.0337(5) Uani 1 1 d . . . O5 O 1.2594(2) 1.1898(2) 0.86030(13) 0.0303(4) Uani 1 1 d . . . O6 O 0.4876(3) 1.3052(3) 1.15217(13) 0.0387(5) Uani 1 1 d . . . O7 O 0.3645(3) 1.4617(3) 1.03882(15) 0.0460(6) Uani 1 1 d . . . S1 S 1.14157(7) 1.31135(8) 0.81957(4) 0.02451(15) 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 0.0203(11) 0.0262(13) 0.0226(10) -0.0023(10) 0.0026(9) -0.0017(10) C2 0.0199(11) 0.0372(19) 0.0355(13) -0.0133(12) 0.0000(9) 0.0024(12) C3 0.0252(11) 0.0233(13) 0.0269(11) -0.0010(12) -0.0075(9) 0.0022(12) C4 0.0206(10) 0.0281(16) 0.0208(10) 0.0006(10) -0.0015(8) 0.0030(11) C5 0.0235(12) 0.0380(17) 0.0225(11) -0.0028(11) 0.0033(9) -0.0030(12) C6 0.0237(11) 0.0322(15) 0.0207(10) 0.0051(11) 0.0015(9) 0.0001(11) C7 0.0188(11) 0.0277(14) 0.0248(11) 0.0027(11) 0.0042(9) 0.0012(10) C8 0.0253(11) 0.0235(14) 0.0192(10) -0.0003(10) 0.0042(9) 0.0005(10) C9 0.0211(11) 0.0412(18) 0.0368(14) -0.0097(13) 0.0020(10) 0.0005(12) C10 0.0266(12) 0.0295(15) 0.0178(10) 0.0049(10) 0.0010(9) 0.0026(11) C11 0.0454(16) 0.0285(16) 0.0472(17) -0.0035(14) -0.0098(14) -0.0052(14) C12 0.0170(9) 0.0229(13) 0.0260(10) -0.0015(11) 0.0000(8) -0.0032(11) C13 0.0260(11) 0.0246(14) 0.0216(11) 0.0040(10) -0.0029(9) -0.0029(11) C14 0.0204(10) 0.0275(14) 0.0265(12) 0.0004(11) -0.0041(9) 0.0017(11) C15 0.0219(11) 0.0253(14) 0.0229(11) -0.0044(10) 0.0016(9) -0.0022(10) C16 0.0310(12) 0.0312(16) 0.0188(10) 0.0038(10) -0.0005(9) -0.0002(11) C17 0.0225(11) 0.0303(14) 0.0244(11) 0.0034(10) -0.0048(9) 0.0037(11) N1 0.0300(11) 0.0349(14) 0.0240(10) -0.0039(9) 0.0030(8) -0.0012(10) O1 0.0276(8) 0.0259(10) 0.0238(8) 0.0010(7) 0.0028(7) -0.0024(8) O2 0.0355(10) 0.0238(10) 0.0408(11) -0.0016(9) -0.0122(8) 0.0007(9) O3 0.0226(8) 0.0366(12) 0.0478(11) 0.0051(9) -0.0070(8) 0.0015(9) O4 0.0295(9) 0.0308(11) 0.0414(11) -0.0022(9) 0.0075(8) -0.0089(9) O5 0.0217(8) 0.0356(11) 0.0333(9) -0.0017(9) -0.0026(7) 0.0022(9) O6 0.0463(10) 0.0407(12) 0.0301(9) 0.0028(10) 0.0151(8) 0.0041(11) O7 0.0302(10) 0.0679(17) 0.0403(11) 0.0039(11) 0.0067(8) 0.0194(11) S1 0.0194(2) 0.0276(3) 0.0266(3) -0.0012(3) 0.00138(19) -0.0027(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 C1 O1 1.456(3) . ? C1 C9 1.515(4) . ? C1 C8 1.548(3) . ? C1 C6 1.547(3) . ? C2 C9 1.520(4) . ? C2 C3 1.559(3) . ? C2 C5 1.561(4) . ? C3 C4 1.551(3) . ? C3 C8 1.562(4) . ? C4 C10 1.474(4) . ? C4 C7 1.563(4) . ? C4 C5 1.583(3) . ? C5 C6 1.554(4) . ? C6 C7 1.566(3) . ? C7 C8 1.567(3) . ? C10 O3 1.199(3) . ? C10 O2 1.338(3) . ? C11 O2 1.450(3) . ? C12 C17 1.383(3) . ? C12 C13 1.389(3) . ? C12 S1 1.771(2) . ? C13 C14 1.382(3) . ? C14 C15 1.378(3) . ? C15 C16 1.377(3) . ? C15 N1 1.481(3) . ? C16 C17 1.384(3) . ? N1 O6 1.222(3) . ? N1 O7 1.225(3) . ? O1 S1 1.5786(17) . ? O4 S1 1.429(2) . ? O5 S1 1.4281(19) . ? 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 C1 C9 117.3(2) . . ? O1 C1 C8 119.6(2) . . ? C9 C1 C8 108.9(2) . . ? O1 C1 C6 111.1(2) . . ? C9 C1 C6 107.8(2) . . ? C8 C1 C6 88.05(17) . . ? C9 C2 C3 107.1(2) . . ? C9 C2 C5 106.1(2) . . ? C3 C2 C5 87.39(17) . . ? C4 C3 C8 90.00(19) . . ? C4 C3 C2 91.81(17) . . ? C8 C3 C2 103.6(2) . . ? C10 C4 C3 128.2(2) . . ? C10 C4 C7 126.9(2) . . ? C3 C4 C7 90.57(18) . . ? C10 C4 C5 122.7(2) . . ? C3 C4 C5 86.91(17) . . ? C7 C4 C5 89.28(19) . . ? C6 C5 C2 103.6(2) . . ? C6 C5 C4 90.09(18) . . ? C2 C5 C4 90.53(18) . . ? C1 C6 C5 102.0(2) . . ? C1 C6 C7 91.39(17) . . ? C5 C6 C7 90.2(2) . . ? C6 C7 C8 86.73(16) . . ? C6 C7 C4 90.40(18) . . ? C8 C7 C4 89.41(18) . . ? C1 C8 C3 101.68(19) . . ? C1 C8 C7 91.34(18) . . ? C3 C8 C7 90.02(18) . . ? C1 C9 C2 95.28(19) . . ? O3 C10 O2 123.3(2) . . ? O3 C10 C4 125.0(2) . . ? O2 C10 C4 111.7(2) . . ? C17 C12 C13 122.0(2) . . ? C17 C12 S1 119.81(18) . . ? C13 C12 S1 118.15(18) . . ? C14 C13 C12 119.2(2) . . ? C15 C14 C13 117.9(2) . . ? C14 C15 C16 123.6(2) . . ? C14 C15 N1 118.1(2) . . ? C16 C15 N1 118.3(2) . . ? C15 C16 C17 118.3(2) . . ? C12 C17 C16 118.9(2) . . ? O6 N1 O7 124.3(2) . . ? O6 N1 C15 118.3(2) . . ? O7 N1 C15 117.4(2) . . ? C1 O1 S1 121.21(15) . . ? C10 O2 C11 115.0(2) . . ? O5 S1 O4 120.11(12) . . ? O5 S1 O1 110.56(11) . . ? O4 S1 O1 103.90(11) . . ? O5 S1 C12 109.26(11) . . ? O4 S1 C12 108.23(12) . . ? O1 S1 C12 103.45(10) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C9 C2 C3 C4 120.0(2) . . . . ? C5 C2 C3 C4 14.0(2) . . . . ? C9 C2 C3 C8 29.5(2) . . . . ? C5 C2 C3 C8 -76.5(2) . . . . ? C8 C3 C4 C10 -139.9(2) . . . . ? C2 C3 C4 C10 116.5(3) . . . . ? C8 C3 C4 C7 0.59(17) . . . . ? C2 C3 C4 C7 -103.0(2) . . . . ? C8 C3 C4 C5 89.84(19) . . . . ? C2 C3 C4 C5 -13.8(2) . . . . ? C9 C2 C5 C6 -30.5(2) . . . . ? C3 C2 C5 C6 76.5(2) . . . . ? C9 C2 C5 C4 -120.7(2) . . . . ? C3 C2 C5 C4 -13.7(2) . . . . ? C10 C4 C5 C6 135.6(2) . . . . ? C3 C4 C5 C6 -89.84(19) . . . . ? C7 C4 C5 C6 0.77(17) . . . . ? C10 C4 C5 C2 -120.8(2) . . . . ? C3 C4 C5 C2 13.8(2) . . . . ? C7 C4 C5 C2 104.37(19) . . . . ? O1 C1 C6 C5 160.40(18) . . . . ? C9 C1 C6 C5 30.7(3) . . . . ? C8 C1 C6 C5 -78.6(2) . . . . ? O1 C1 C6 C7 -109.1(2) . . . . ? C9 C1 C6 C7 121.2(2) . . . . ? C8 C1 C6 C7 12.0(2) . . . . ? C2 C5 C6 C1 0.1(2) . . . . ? C4 C5 C6 C1 90.70(18) . . . . ? C2 C5 C6 C7 -91.3(2) . . . . ? C4 C5 C6 C7 -0.77(17) . . . . ? C1 C6 C7 C8 -11.8(2) . . . . ? C5 C6 C7 C8 90.16(18) . . . . ? C1 C6 C7 C4 -101.23(19) . . . . ? C5 C6 C7 C4 0.78(17) . . . . ? C10 C4 C7 C6 -132.5(2) . . . . ? C3 C4 C7 C6 86.14(17) . . . . ? C5 C4 C7 C6 -0.76(17) . . . . ? C10 C4 C7 C8 140.7(2) . . . . ? C3 C4 C7 C8 -0.59(17) . . . . ? C5 C4 C7 C8 -87.49(16) . . . . ? O1 C1 C8 C3 -168.46(19) . . . . ? C9 C1 C8 C3 -29.8(2) . . . . ? C6 C1 C8 C3 78.3(2) . . . . ? O1 C1 C8 C7 101.3(2) . . . . ? C9 C1 C8 C7 -120.1(2) . . . . ? C6 C1 C8 C7 -12.0(2) . . . . ? C4 C3 C8 C1 -91.96(19) . . . . ? C2 C3 C8 C1 -0.1(2) . . . . ? C4 C3 C8 C7 -0.59(17) . . . . ? C2 C3 C8 C7 91.27(18) . . . . ? C6 C7 C8 C1 11.8(2) . . . . ? C4 C7 C8 C1 102.27(19) . . . . ? C6 C7 C8 C3 -89.85(19) . . . . ? C4 C7 C8 C3 0.58(17) . . . . ? O1 C1 C9 C2 -174.0(2) . . . . ? C8 C1 C9 C2 46.3(2) . . . . ? C6 C1 C9 C2 -47.8(3) . . . . ? C3 C2 C9 C1 -45.3(2) . . . . ? C5 C2 C9 C1 46.9(2) . . . . ? C3 C4 C10 O3 162.6(3) . . . . ? C7 C4 C10 O3 35.3(4) . . . . ? C5 C4 C10 O3 -82.3(3) . . . . ? C3 C4 C10 O2 -19.6(3) . . . . ? C7 C4 C10 O2 -146.9(2) . . . . ? C5 C4 C10 O2 95.5(3) . . . . ? C17 C12 C13 C14 -0.2(4) . . . . ? S1 C12 C13 C14 -179.4(2) . . . . ? C12 C13 C14 C15 0.2(4) . . . . ? C13 C14 C15 C16 -0.2(4) . . . . ? C13 C14 C15 N1 -178.8(2) . . . . ? C14 C15 C16 C17 0.3(4) . . . . ? N1 C15 C16 C17 178.9(2) . . . . ? C13 C12 C17 C16 0.3(4) . . . . ? S1 C12 C17 C16 179.5(2) . . . . ? C15 C16 C17 C12 -0.4(4) . . . . ? C14 C15 N1 O6 174.4(3) . . . . ? C16 C15 N1 O6 -4.2(4) . . . . ? C14 C15 N1 O7 -5.1(3) . . . . ? C16 C15 N1 O7 176.2(2) . . . . ? C9 C1 O1 S1 -80.7(2) . . . . ? C8 C1 O1 S1 54.6(3) . . . . ? C6 C1 O1 S1 154.78(15) . . . . ? O3 C10 O2 C11 -0.4(4) . . . . ? C4 C10 O2 C11 -178.2(2) . . . . ? C1 O1 S1 O5 32.49(19) . . . . ? C1 O1 S1 O4 162.64(17) . . . . ? C1 O1 S1 C12 -84.37(19) . . . . ? C17 C12 S1 O5 14.3(3) . . . . ? C13 C12 S1 O5 -166.5(2) . . . . ? C17 C12 S1 O4 -118.1(2) . . . . ? C13 C12 S1 O4 61.1(2) . . . . ? C17 C12 S1 O1 132.1(2) . . . . ? C13 C12 S1 O1 -48.7(2) . . . . ? _diffrn_measured_fraction_theta_max 0.882 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.422 _refine_diff_density_min -0.290 _refine_diff_density_rms 0.047