# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_11m_cdkadushan2_0s-cmpd16 _database_code_depnum_ccdc_archive 'CCDC 885420' #TrackingRef 'Pillay_Rousseau_Fernandes_deKoning-organic_biomolecular_chemistry.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H16 O6' _chemical_formula_sum 'C16 H16 O6' _chemical_formula_weight 304.29 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/m _symmetry_space_group_name_Hall '-C 2y' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x, -y, z' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z' _cell_length_a 19.2003(6) _cell_length_b 6.7203(2) _cell_length_c 11.0340(4) _cell_angle_alpha 90.00 _cell_angle_beta 99.379(2) _cell_angle_gamma 90.00 _cell_volume 1404.70(8) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2971 _cell_measurement_theta_min 2.61 _cell_measurement_theta_max 28.24 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.439 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 640 _exptl_absorpt_coefficient_mu 0.111 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9550 _exptl_absorpt_correction_T_max 0.9760 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8613 _diffrn_reflns_av_R_equivalents 0.0473 _diffrn_reflns_av_sigmaI/netI 0.0330 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.87 _diffrn_reflns_theta_max 27.99 _reflns_number_total 1842 _reflns_number_gt 1398 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0772P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1842 _refine_ls_number_parameters 140 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0561 _refine_ls_R_factor_gt 0.0439 _refine_ls_wR_factor_ref 0.1261 _refine_ls_wR_factor_gt 0.1176 _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_restrained_S_all 1.069 _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 0.35543(8) 0.0000 0.49614(15) 0.0213(3) Uani 1 2 d S . . C2 C 0.31914(7) 0.0000 0.37310(14) 0.0198(3) Uani 1 2 d S . . C3 C 0.35642(8) 0.0000 0.27240(14) 0.0232(4) Uani 1 2 d S . . H3 H 0.4066 0.0000 0.2857 0.028 Uiso 1 2 calc SR . . C4 C 0.31905(8) 0.0000 0.15587(15) 0.0238(4) Uani 1 2 d S . . C5 C 0.24422(8) 0.0000 0.13436(14) 0.0237(4) Uani 1 2 d S . . H5 H 0.2191 0.0000 0.0527 0.028 Uiso 1 2 calc SR . . C6 C 0.20831(7) 0.0000 0.23209(14) 0.0210(3) Uani 1 2 d S . . C7 C 0.24480(7) 0.0000 0.35570(13) 0.0187(3) Uani 1 2 d S . . C8 C 0.20806(8) 0.0000 0.45756(14) 0.0190(3) Uani 1 2 d S . . H8 H 0.1579 0.0000 0.4436 0.023 Uiso 1 2 calc SR . . C9 C 0.24352(8) 0.0000 0.57466(13) 0.0188(3) Uani 1 2 d S . . C10 C 0.31928(8) 0.0000 0.59625(14) 0.0208(3) Uani 1 2 d S . . C11 C 0.42324(8) 0.0000 0.06567(16) 0.0338(4) Uani 1 2 d S . . H11A H 0.4381 0.0000 -0.0152 0.051 Uiso 1 2 calc SR . . H11B H 0.4416 -0.1191 0.1113 0.051 Uiso 0.50 1 calc PR . . H11C H 0.4416 0.1191 0.1113 0.051 Uiso 0.50 1 calc PR . . C12 C 0.09815(9) 0.0000 0.09875(16) 0.0436(5) Uani 1 2 d S . . H12A H 0.0475 0.0102 0.1015 0.065 Uiso 0.50 1 calc PR . . H12B H 0.1076 -0.1239 0.0574 0.065 Uiso 0.50 1 calc PR . . H12C H 0.1130 0.1136 0.0534 0.065 Uiso 0.50 1 calc PR . . C13 C 0.20460(8) 0.0000 0.68320(13) 0.0216(3) Uani 1 2 d S A . H13A H 0.2174 -0.1195 0.7345 0.026 Uiso 0.50 1 calc PR . . H13B H 0.2174 0.1195 0.7345 0.026 Uiso 0.50 1 calc PR . . C14 C 0.35952(8) 0.0000 0.71881(15) 0.0282(4) Uani 1 2 d S . . H14 H 0.3340 0.0000 0.7857 0.034 Uiso 1 2 calc SR . . C15 C 0.08763(11) 0.0287(12) 0.72180(19) 0.0262(15) Uani 0.50 1 d P A -1 C16 C 0.01252(12) 0.0557(4) 0.6628(2) 0.0446(10) Uani 0.50 1 d P A -1 H16A H -0.0087 -0.0745 0.6405 0.067 Uiso 0.50 1 calc PR A -1 H16B H 0.0107 0.1373 0.5887 0.067 Uiso 0.50 1 calc PR A -1 H16C H -0.0137 0.1222 0.7204 0.067 Uiso 0.50 1 calc PR A -1 O1 O 0.42614(5) 0.0000 0.51025(11) 0.0317(3) Uani 1 2 d S . . H1 H 0.4429 0.0000 0.5855 0.048 Uiso 1 2 calc SR . . O2 O 0.34800(6) 0.0000 0.05060(10) 0.0321(3) Uani 1 2 d S . . O3 O 0.13673(5) 0.0000 0.22131(9) 0.0290(3) Uani 1 2 d S . . O4 O 0.13066(6) 0.0000 0.63680(10) 0.0323(3) Uani 1 2 d S . . O5 O 0.10814(7) 0.0000 0.82937(11) 0.0430(4) Uani 1 2 d S . . O6 O 0.42454(6) 0.0000 0.74310(11) 0.0383(4) Uani 1 2 d S . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0167(7) 0.0222(8) 0.0239(8) 0.000 0.0002(6) 0.000 C2 0.0197(7) 0.0188(7) 0.0210(8) 0.000 0.0036(6) 0.000 C3 0.0174(7) 0.0268(8) 0.0260(9) 0.000 0.0057(6) 0.000 C4 0.0241(8) 0.0286(8) 0.0209(8) 0.000 0.0099(6) 0.000 C5 0.0229(8) 0.0327(9) 0.0154(7) 0.000 0.0027(6) 0.000 C6 0.0164(7) 0.0262(8) 0.0202(8) 0.000 0.0022(6) 0.000 C7 0.0199(7) 0.0179(7) 0.0183(8) 0.000 0.0032(6) 0.000 C8 0.0180(7) 0.0197(7) 0.0195(8) 0.000 0.0043(6) 0.000 C9 0.0217(7) 0.0167(7) 0.0179(8) 0.000 0.0032(6) 0.000 C10 0.0224(8) 0.0201(7) 0.0190(8) 0.000 0.0006(6) 0.000 C11 0.0228(8) 0.0540(11) 0.0275(10) 0.000 0.0127(7) 0.000 C12 0.0246(8) 0.0862(15) 0.0180(9) 0.000 -0.0022(7) 0.000 C13 0.0240(8) 0.0248(8) 0.0154(7) 0.000 0.0018(6) 0.000 C14 0.0263(8) 0.0348(9) 0.0217(9) 0.000 -0.0010(7) 0.000 C15 0.0329(10) 0.024(5) 0.0249(10) 0.0008(11) 0.0148(8) -0.0024(11) C16 0.0297(11) 0.070(3) 0.0370(13) 0.0002(12) 0.0134(10) 0.0019(11) O1 0.0161(5) 0.0516(8) 0.0263(6) 0.000 0.0002(5) 0.000 O2 0.0231(6) 0.0546(8) 0.0209(6) 0.000 0.0106(5) 0.000 O3 0.0171(5) 0.0540(8) 0.0153(6) 0.000 0.0008(4) 0.000 O4 0.0214(6) 0.0586(8) 0.0182(6) 0.000 0.0070(4) 0.000 O5 0.0461(8) 0.0654(9) 0.0206(7) 0.000 0.0145(6) 0.000 O6 0.0256(6) 0.0586(9) 0.0275(7) 0.000 -0.0053(5) 0.000 _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 1.3410(17) . ? C1 C10 1.397(2) . ? C1 C2 1.421(2) . ? C2 C7 1.4090(19) . ? C2 C3 1.416(2) . ? C3 C4 1.367(2) . ? C3 H3 0.9500 . ? C4 O2 1.3670(18) . ? C4 C5 1.417(2) . ? C5 C6 1.371(2) . ? C5 H5 0.9500 . ? C6 O3 1.3601(16) . ? C6 C7 1.428(2) . ? C7 C8 1.421(2) . ? C8 C9 1.359(2) . ? C8 H8 0.9500 . ? C9 C10 1.4353(19) . ? C9 C13 1.511(2) . ? C10 C14 1.444(2) . ? C11 O2 1.4269(18) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 O3 1.4320(18) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 O4 1.4285(17) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 O6 1.2333(19) . ? C14 H14 0.9500 . ? C15 O5 1.204(3) . ? C15 O4 1.361(2) . ? C15 C16 1.494(3) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? O1 H1 0.8400 . ? O4 C15 1.361(2) 6 ? O5 C15 1.204(3) 6 ? 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 C10 122.15(14) . . ? O1 C1 C2 116.13(13) . . ? C10 C1 C2 121.72(14) . . ? C7 C2 C3 121.56(14) . . ? C7 C2 C1 117.27(14) . . ? C3 C2 C1 121.16(14) . . ? C4 C3 C2 118.89(13) . . ? C4 C3 H3 120.6 . . ? C2 C3 H3 120.6 . . ? C3 C4 O2 125.15(14) . . ? C3 C4 C5 121.33(14) . . ? O2 C4 C5 113.52(14) . . ? C6 C5 C4 119.61(14) . . ? C6 C5 H5 120.2 . . ? C4 C5 H5 120.2 . . ? O3 C6 C5 124.17(14) . . ? O3 C6 C7 114.52(13) . . ? C5 C6 C7 121.31(13) . . ? C2 C7 C8 120.98(13) . . ? C2 C7 C6 117.29(13) . . ? C8 C7 C6 121.73(13) . . ? C9 C8 C7 121.04(13) . . ? C9 C8 H8 119.5 . . ? C7 C8 H8 119.5 . . ? C8 C9 C10 119.68(14) . . ? C8 C9 C13 121.18(13) . . ? C10 C9 C13 119.15(13) . . ? C1 C10 C9 119.30(14) . . ? C1 C10 C14 118.78(14) . . ? C9 C10 C14 121.91(14) . . ? 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 . . ? O3 C12 H12A 109.5 . . ? O3 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? O3 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? O4 C13 C9 107.87(12) . . ? O4 C13 H13A 110.1 . . ? C9 C13 H13A 110.1 . . ? O4 C13 H13B 110.1 . . ? C9 C13 H13B 110.1 . . ? H13A C13 H13B 108.4 . . ? O6 C14 C10 124.87(16) . . ? O6 C14 H14 117.6 . . ? C10 C14 H14 117.6 . . ? O5 C15 O4 121.3(3) . . ? O5 C15 C16 125.95(19) . . ? O4 C15 C16 111.60(18) . . ? C1 O1 H1 109.5 . . ? C4 O2 C11 116.43(13) . . ? C6 O3 C12 116.26(12) . . ? C15 O4 C13 115.63(14) 6 . ? C15 O4 C13 115.63(14) . . ? 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 O1 C1 C2 C7 180.0 . . . . ? C10 C1 C2 C7 0.0 . . . . ? O1 C1 C2 C3 0.0 . . . . ? C10 C1 C2 C3 180.0 . . . . ? C7 C2 C3 C4 0.0 . . . . ? C1 C2 C3 C4 180.0 . . . . ? C2 C3 C4 O2 180.0 . . . . ? C2 C3 C4 C5 0.0 . . . . ? C3 C4 C5 C6 0.0 . . . . ? O2 C4 C5 C6 180.0 . . . . ? C4 C5 C6 O3 180.0 . . . . ? C4 C5 C6 C7 0.0 . . . . ? C3 C2 C7 C8 180.0 . . . . ? C1 C2 C7 C8 0.0 . . . . ? C3 C2 C7 C6 0.0 . . . . ? C1 C2 C7 C6 180.0 . . . . ? O3 C6 C7 C2 180.0 . . . . ? C5 C6 C7 C2 0.0 . . . . ? O3 C6 C7 C8 0.0 . . . . ? C5 C6 C7 C8 180.0 . . . . ? C2 C7 C8 C9 0.0 . . . . ? C6 C7 C8 C9 180.0 . . . . ? C7 C8 C9 C10 0.0 . . . . ? C7 C8 C9 C13 180.0 . . . . ? O1 C1 C10 C9 180.0 . . . . ? C2 C1 C10 C9 0.0 . . . . ? O1 C1 C10 C14 0.0 . . . . ? C2 C1 C10 C14 180.0 . . . . ? C8 C9 C10 C1 0.0 . . . . ? C13 C9 C10 C1 180.0 . . . . ? C8 C9 C10 C14 180.0 . . . . ? C13 C9 C10 C14 0.0 . . . . ? C8 C9 C13 O4 0.0 . . . . ? C10 C9 C13 O4 180.0 . . . . ? C1 C10 C14 O6 0.0 . . . . ? C9 C10 C14 O6 180.0 . . . . ? C3 C4 O2 C11 0.0 . . . . ? C5 C4 O2 C11 180.0 . . . . ? C5 C6 O3 C12 0.0 . . . . ? C7 C6 O3 C12 180.0 . . . . ? O5 C15 O4 C15 74.0(6) . . . 6 ? C16 C15 O4 C15 -94.3(5) . . . 6 ? O5 C15 O4 C13 -20.0(8) . . . . ? C16 C15 O4 C13 171.7(3) . . . . ? C9 C13 O4 C15 171.0(4) . . . 6 ? C9 C13 O4 C15 -171.0(4) . . . . ? O4 C15 O5 C15 -74.5(6) . . . 6 ? C16 C15 O5 C15 92.0(7) . . . 6 ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.99 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.247 _refine_diff_density_min -0.363 _refine_diff_density_rms 0.098 data_11m_cdk_adushan4_0s-cmpd17 _database_code_depnum_ccdc_archive 'CCDC 885421' #TrackingRef 'Pillay_Rousseau_Fernandes_deKoning-organic_biomolecular_chemistry.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H15 N O9' _chemical_formula_sum 'C16 H15 N O9' _chemical_formula_weight 365.29 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c _symmetry_space_group_name_Hall '-P 2ybc' 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 13.913(4) _cell_length_b 13.475(4) _cell_length_c 8.404(3) _cell_angle_alpha 90.00 _cell_angle_beta 94.246(9) _cell_angle_gamma 90.00 _cell_volume 1571.2(9) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 925 _cell_measurement_theta_min 2.94 _cell_measurement_theta_max 24.35 _exptl_crystal_description needle _exptl_crystal_colour brown _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.544 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 760 _exptl_absorpt_coefficient_mu 0.129 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7954 _diffrn_reflns_av_R_equivalents 0.1022 _diffrn_reflns_av_sigmaI/netI 0.1561 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.47 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2722 _reflns_number_gt 1010 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0354P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2722 _refine_ls_number_parameters 239 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1857 _refine_ls_R_factor_gt 0.0497 _refine_ls_wR_factor_ref 0.1160 _refine_ls_wR_factor_gt 0.0821 _refine_ls_goodness_of_fit_ref 0.874 _refine_ls_restrained_S_all 0.874 _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 0.7945(3) 0.1080(3) 0.4411(5) 0.0281(11) Uani 1 1 d . . . C2 C 0.7955(3) 0.2193(3) 0.4379(5) 0.0270(11) Uani 1 1 d . . . C3 C 0.8691(3) 0.2662(3) 0.5322(5) 0.0308(12) Uani 1 1 d . . . H3 H 0.9152 0.2288 0.5961 0.037 Uiso 1 1 calc R . . C4 C 0.8726(3) 0.3694(4) 0.5297(5) 0.0346(12) Uani 1 1 d . . . C5 C 0.8058(3) 0.4232(3) 0.4356(5) 0.0363(12) Uani 1 1 d . . . H5 H 0.8099 0.4935 0.4353 0.044 Uiso 1 1 calc R . . C6 C 0.7334(3) 0.3772(3) 0.3420(5) 0.0290(11) Uani 1 1 d . . . C7 C 0.7251(3) 0.2724(3) 0.3442(5) 0.0287(11) Uani 1 1 d . . . C8 C 0.6490(3) 0.2185(3) 0.2524(5) 0.0317(12) Uani 1 1 d . . . C9 C 0.6534(3) 0.1081(3) 0.2477(5) 0.0278(11) Uani 1 1 d . . . C10 C 0.7196(3) 0.0571(3) 0.3377(5) 0.0279(11) Uani 1 1 d . . . C11 C 1.0123(3) 0.3787(3) 0.7148(5) 0.0470(14) Uani 1 1 d . . . H11A H 0.9841 0.3330 0.7891 0.070 Uiso 1 1 calc R . . H11B H 1.0507 0.4289 0.7752 0.070 Uiso 1 1 calc R . . H11C H 1.0537 0.3417 0.6464 0.070 Uiso 1 1 calc R . . C12 C 0.6764(3) 0.5339(3) 0.2411(5) 0.0424(13) Uani 1 1 d . . . H12A H 0.6677 0.5617 0.3468 0.064 Uiso 1 1 calc R . . H12B H 0.6272 0.5609 0.1635 0.064 Uiso 1 1 calc R . . H12C H 0.7405 0.5514 0.2090 0.064 Uiso 1 1 calc R . . C13 C 0.5786(3) 0.0576(3) 0.1393(5) 0.0357(12) Uani 1 1 d . . . H13A H 0.5157 0.0620 0.1864 0.043 Uiso 1 1 calc R . . H13B H 0.5728 0.0929 0.0357 0.043 Uiso 1 1 calc R . . C14 C 0.7220(3) -0.0544(3) 0.3320(5) 0.0321(12) Uani 1 1 d . . . H14 H 0.7358 -0.0822 0.4416 0.039 Uiso 1 1 calc R . . C15 C 0.6283(3) -0.0989(4) 0.2535(5) 0.0358(12) Uani 1 1 d . . . C16 C 0.6377(3) -0.2054(3) 0.2016(5) 0.0440(13) Uani 1 1 d . . . H16A H 0.6593 -0.2463 0.2939 0.066 Uiso 1 1 calc R . . H16B H 0.6848 -0.2097 0.1208 0.066 Uiso 1 1 calc R . . H16C H 0.5750 -0.2295 0.1563 0.066 Uiso 1 1 calc R . . N1 N 0.8732(3) -0.1393(3) 0.3048(6) 0.0551(12) Uani 1 1 d . . . O1 O 0.85381(18) 0.0597(2) 0.5232(3) 0.0362(8) Uani 1 1 d . . . O2 O 0.9372(2) 0.4262(2) 0.6185(4) 0.0444(8) Uani 1 1 d . . . O3 O 0.66721(19) 0.4274(2) 0.2468(3) 0.0375(8) Uani 1 1 d . . . O4 O 0.5792(2) 0.2579(2) 0.1775(3) 0.0467(9) Uani 1 1 d . . . O5 O 0.60026(19) -0.0441(2) 0.1120(3) 0.0369(8) Uani 1 1 d . . . O6 O 0.56119(19) -0.0862(2) 0.3695(3) 0.0429(9) Uani 1 1 d . . . H6 H 0.5116 -0.1199 0.3442 0.064 Uiso 1 1 calc R . . O7 O 0.79979(19) -0.0789(2) 0.2317(3) 0.0387(8) Uani 1 1 d . . . O8 O 0.8618(3) -0.1766(3) 0.4321(5) 0.0752(13) Uani 1 1 d . . . O9 O 0.9389(2) -0.1480(3) 0.2182(4) 0.0763(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 0.022(2) 0.035(3) 0.027(3) 0.000(2) 0.003(2) -0.001(2) C2 0.030(3) 0.028(3) 0.023(3) -0.003(2) 0.003(2) -0.003(2) C3 0.025(3) 0.036(3) 0.032(3) -0.002(2) 0.003(2) 0.005(2) C4 0.030(3) 0.041(4) 0.032(3) -0.009(2) -0.001(2) 0.000(2) C5 0.037(3) 0.033(3) 0.038(3) 0.000(3) 0.002(2) 0.003(3) C6 0.026(3) 0.038(3) 0.023(3) 0.004(2) -0.001(2) 0.003(2) C7 0.030(3) 0.034(3) 0.022(3) 0.001(2) -0.001(2) 0.002(2) C8 0.026(3) 0.036(3) 0.033(3) -0.003(2) -0.001(2) 0.003(2) C9 0.021(2) 0.038(3) 0.024(3) -0.004(2) -0.002(2) 0.000(2) C10 0.027(2) 0.028(3) 0.028(3) -0.003(2) 0.002(2) -0.002(2) C11 0.035(3) 0.054(4) 0.050(3) -0.006(3) -0.012(2) -0.001(2) C12 0.052(3) 0.035(3) 0.041(3) 0.010(2) 0.005(3) 0.012(3) C13 0.032(3) 0.035(3) 0.038(3) -0.002(2) -0.007(2) 0.003(2) C14 0.028(2) 0.044(3) 0.025(3) -0.003(2) 0.003(2) -0.004(2) C15 0.032(3) 0.044(3) 0.031(3) -0.003(2) -0.002(2) -0.006(2) C16 0.055(3) 0.035(3) 0.041(3) -0.005(3) -0.004(3) -0.006(3) N1 0.048(3) 0.040(3) 0.077(4) 0.002(3) 0.003(3) 0.015(3) O1 0.0341(17) 0.035(2) 0.0373(19) 0.0013(16) -0.0144(15) 0.0014(15) O2 0.0435(18) 0.035(2) 0.052(2) -0.0083(17) -0.0141(16) 0.0005(17) O3 0.0427(18) 0.033(2) 0.036(2) 0.0050(16) -0.0051(15) 0.0065(17) O4 0.0375(19) 0.043(2) 0.056(2) -0.0067(18) -0.0177(17) 0.0108(16) O5 0.0369(18) 0.043(2) 0.0295(18) -0.0052(16) -0.0085(14) -0.0030(16) O6 0.0347(17) 0.052(2) 0.0416(19) -0.0065(17) 0.0030(15) -0.0158(17) O7 0.0346(17) 0.037(2) 0.044(2) 0.0047(17) 0.0000(16) 0.0071(16) O8 0.095(3) 0.069(3) 0.061(3) 0.017(2) -0.004(2) 0.036(2) O9 0.057(3) 0.057(3) 0.117(4) 0.012(2) 0.024(2) 0.025(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.223(4) . ? C1 C10 1.475(5) . ? C1 C2 1.501(5) . ? C2 C3 1.398(5) . ? C2 C7 1.406(5) . ? C3 C4 1.392(6) . ? C3 H3 0.9500 . ? C4 O2 1.361(5) . ? C4 C5 1.380(5) . ? C5 C6 1.379(5) . ? C5 H5 0.9500 . ? C6 O3 1.354(4) . ? C6 C7 1.417(5) . ? C7 C8 1.457(5) . ? C8 O4 1.237(5) . ? C8 C9 1.490(6) . ? C9 C10 1.338(5) . ? C9 C13 1.495(5) . ? C10 C14 1.504(5) . ? C11 O2 1.425(4) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 O3 1.442(4) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 O5 1.425(4) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 O7 1.458(4) . ? C14 C15 1.539(5) . ? C14 H14 1.0000 . ? C15 O6 1.409(4) . ? C15 O5 1.430(5) . ? C15 C16 1.510(5) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? N1 O8 1.203(5) . ? N1 O9 1.216(4) . ? N1 O7 1.411(4) . ? O6 H6 0.8400 . ? 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 C10 120.2(4) . . ? O1 C1 C2 122.3(4) . . ? C10 C1 C2 117.4(4) . . ? C3 C2 C7 122.5(4) . . ? C3 C2 C1 116.7(4) . . ? C7 C2 C1 120.8(4) . . ? C4 C3 C2 117.9(4) . . ? C4 C3 H3 121.1 . . ? C2 C3 H3 121.1 . . ? O2 C4 C5 114.1(4) . . ? O2 C4 C3 125.2(4) . . ? C5 C4 C3 120.7(4) . . ? C6 C5 C4 121.6(4) . . ? C6 C5 H5 119.2 . . ? C4 C5 H5 119.2 . . ? O3 C6 C5 123.3(4) . . ? O3 C6 C7 116.9(4) . . ? C5 C6 C7 119.8(4) . . ? C2 C7 C6 117.4(4) . . ? C2 C7 C8 119.5(4) . . ? C6 C7 C8 123.1(4) . . ? O4 C8 C7 124.6(4) . . ? O4 C8 C9 116.6(4) . . ? C7 C8 C9 118.8(4) . . ? C10 C9 C8 121.7(4) . . ? C10 C9 C13 122.0(4) . . ? C8 C9 C13 116.3(4) . . ? C9 C10 C1 121.4(4) . . ? C9 C10 C14 120.7(4) . . ? C1 C10 C14 117.8(4) . . ? 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 . . ? O3 C12 H12A 109.5 . . ? O3 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? O3 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? O5 C13 C9 113.0(3) . . ? O5 C13 H13A 109.0 . . ? C9 C13 H13A 109.0 . . ? O5 C13 H13B 109.0 . . ? C9 C13 H13B 109.0 . . ? H13A C13 H13B 107.8 . . ? O7 C14 C10 105.3(3) . . ? O7 C14 C15 107.8(3) . . ? C10 C14 C15 112.5(4) . . ? O7 C14 H14 110.3 . . ? C10 C14 H14 110.3 . . ? C15 C14 H14 110.3 . . ? O6 C15 O5 111.0(4) . . ? O6 C15 C16 113.0(4) . . ? O5 C15 C16 106.0(3) . . ? O6 C15 C14 103.9(3) . . ? O5 C15 C14 109.0(4) . . ? C16 C15 C14 113.9(4) . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? O8 N1 O9 130.3(5) . . ? O8 N1 O7 119.3(4) . . ? O9 N1 O7 110.3(4) . . ? C4 O2 C11 119.0(4) . . ? C6 O3 C12 117.3(3) . . ? C13 O5 C15 114.2(3) . . ? C15 O6 H6 109.5 . . ? N1 O7 C14 115.0(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 O1 C1 C2 C3 1.0(6) . . . . ? C10 C1 C2 C3 -177.8(4) . . . . ? O1 C1 C2 C7 -178.8(4) . . . . ? C10 C1 C2 C7 2.4(6) . . . . ? C7 C2 C3 C4 -1.2(6) . . . . ? C1 C2 C3 C4 179.0(4) . . . . ? C2 C3 C4 O2 177.6(4) . . . . ? C2 C3 C4 C5 -0.5(6) . . . . ? O2 C4 C5 C6 -177.9(4) . . . . ? C3 C4 C5 C6 0.4(7) . . . . ? C4 C5 C6 O3 -179.2(4) . . . . ? C4 C5 C6 C7 1.5(7) . . . . ? C3 C2 C7 C6 3.0(6) . . . . ? C1 C2 C7 C6 -177.3(4) . . . . ? C3 C2 C7 C8 -178.2(4) . . . . ? C1 C2 C7 C8 1.5(6) . . . . ? O3 C6 C7 C2 177.6(4) . . . . ? C5 C6 C7 C2 -3.1(6) . . . . ? O3 C6 C7 C8 -1.1(6) . . . . ? C5 C6 C7 C8 178.2(4) . . . . ? C2 C7 C8 O4 173.5(4) . . . . ? C6 C7 C8 O4 -7.8(7) . . . . ? C2 C7 C8 C9 -6.0(6) . . . . ? C6 C7 C8 C9 172.7(4) . . . . ? O4 C8 C9 C10 -172.7(4) . . . . ? C7 C8 C9 C10 6.8(6) . . . . ? O4 C8 C9 C13 6.1(6) . . . . ? C7 C8 C9 C13 -174.4(4) . . . . ? C8 C9 C10 C1 -2.8(6) . . . . ? C13 C9 C10 C1 178.4(4) . . . . ? C8 C9 C10 C14 179.4(4) . . . . ? C13 C9 C10 C14 0.6(6) . . . . ? O1 C1 C10 C9 179.5(4) . . . . ? C2 C1 C10 C9 -1.8(6) . . . . ? O1 C1 C10 C14 -2.7(6) . . . . ? C2 C1 C10 C14 176.1(3) . . . . ? C10 C9 C13 O5 -15.0(6) . . . . ? C8 C9 C13 O5 166.1(3) . . . . ? C9 C10 C14 O7 101.4(4) . . . . ? C1 C10 C14 O7 -76.5(4) . . . . ? C9 C10 C14 C15 -15.8(5) . . . . ? C1 C10 C14 C15 166.4(3) . . . . ? O7 C14 C15 O6 170.7(3) . . . . ? C10 C14 C15 O6 -73.6(4) . . . . ? O7 C14 C15 O5 -70.9(4) . . . . ? C10 C14 C15 O5 44.8(5) . . . . ? O7 C14 C15 C16 47.2(5) . . . . ? C10 C14 C15 C16 162.9(4) . . . . ? C5 C4 O2 C11 -177.2(4) . . . . ? C3 C4 O2 C11 4.6(6) . . . . ? C5 C6 O3 C12 2.1(6) . . . . ? C7 C6 O3 C12 -178.7(3) . . . . ? C9 C13 O5 C15 47.5(5) . . . . ? O6 C15 O5 C13 51.1(4) . . . . ? C16 C15 O5 C13 174.3(3) . . . . ? C14 C15 O5 C13 -62.7(4) . . . . ? O8 N1 O7 C14 9.6(6) . . . . ? O9 N1 O7 C14 -173.5(4) . . . . ? C10 C14 O7 N1 122.3(3) . . . . ? C15 C14 O7 N1 -117.3(4) . . . . ? 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 O6 H6 O4 0.84 2.08 2.876(4) 159.2 2_645 _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.184 _refine_diff_density_min -0.196 _refine_diff_density_rms 0.052 data_12m_cdkadushan1_0s-cmpd29 _database_code_depnum_ccdc_archive 'CCDC 885422' #TrackingRef 'Pillay_Rousseau_Fernandes_deKoning-organic_biomolecular_chemistry.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H16 O6' _chemical_formula_sum 'C17 H16 O6' _chemical_formula_weight 316.30 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.4652(2) _cell_length_b 9.6050(2) _cell_length_c 9.6340(2) _cell_angle_alpha 111.5360(10) _cell_angle_beta 90.649(2) _cell_angle_gamma 98.224(2) _cell_volume 719.41(3) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4715 _cell_measurement_theta_min 2.28 _cell_measurement_theta_max 27.86 _exptl_crystal_description plate _exptl_crystal_colour brown _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.460 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 332 _exptl_absorpt_coefficient_mu 0.111 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17177 _diffrn_reflns_av_R_equivalents 0.0442 _diffrn_reflns_av_sigmaI/netI 0.0338 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.28 _diffrn_reflns_theta_max 28.00 _reflns_number_total 3470 _reflns_number_gt 2420 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0749P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3470 _refine_ls_number_parameters 212 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0665 _refine_ls_R_factor_gt 0.0421 _refine_ls_wR_factor_ref 0.1269 _refine_ls_wR_factor_gt 0.1150 _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_restrained_S_all 1.017 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.81454(15) 1.07994(14) 0.43421(15) 0.0212(3) Uani 1 1 d . . . C2 C 0.85556(15) 1.10469(15) 0.58381(15) 0.0218(3) Uani 1 1 d . . . C3 C 0.96956(16) 1.24169(15) 0.67818(16) 0.0259(3) Uani 1 1 d . . . C4 C 1.01787(15) 1.25394(16) 0.83217(15) 0.0256(3) Uani 1 1 d . . . C5 C 0.95698(17) 1.15118(16) 0.88820(16) 0.0285(3) Uani 1 1 d . . . H5 H 0.9903 1.1649 0.9875 0.034 Uiso 1 1 calc R . . C6 C 0.84110(16) 1.01861(16) 0.80176(15) 0.0266(3) Uani 1 1 d . . . C7 C 0.78852(15) 0.99879(15) 0.64627(15) 0.0220(3) Uani 1 1 d . . . C8 C 0.67563(15) 0.87470(15) 0.55822(15) 0.0231(3) Uani 1 1 d . . . C9 C 0.63382(16) 0.85436(15) 0.41172(15) 0.0237(3) Uani 1 1 d . . . C10 C 0.70245(15) 0.95403(15) 0.34729(15) 0.0227(3) Uani 1 1 d . . . C11 C 0.8143(2) 1.29465(19) 0.3688(2) 0.0412(4) Uani 1 1 d . . . H11A H 0.7006 1.2592 0.3366 0.062 Uiso 1 1 calc R . . H11B H 0.8652 1.3414 0.3023 0.062 Uiso 1 1 calc R . . H11C H 0.8251 1.3694 0.4715 0.062 Uiso 1 1 calc R . . C12 C 1.1724(2) 1.40750(18) 1.05581(17) 0.0384(4) Uani 1 1 d . . . H12A H 1.0780 1.4188 1.1146 0.058 Uiso 1 1 calc R . . H12B H 1.2506 1.5007 1.0964 0.058 Uiso 1 1 calc R . . H12C H 1.2204 1.3223 1.0608 0.058 Uiso 1 1 calc R . . C13 C 0.6881(2) 0.64823(17) 0.59612(19) 0.0386(4) Uani 1 1 d . . . H13A H 0.6933 0.5880 0.4897 0.058 Uiso 1 1 calc R . . H13B H 0.6339 0.5836 0.6453 0.058 Uiso 1 1 calc R . . H13C H 0.7967 0.6899 0.6426 0.058 Uiso 1 1 calc R . . C14 C 0.52269(18) 0.71482(17) 0.31214(17) 0.0319(3) Uani 1 1 d . . . H14A H 0.5858 0.6323 0.2657 0.038 Uiso 1 1 calc R . . H14B H 0.4451 0.6814 0.3741 0.038 Uiso 1 1 calc R . . C15 C 0.65474(16) 0.92181(16) 0.19162(15) 0.0258(3) Uani 1 1 d . . . H15 H 0.7153 0.9735 0.1377 0.031 Uiso 1 1 calc R . . C16 C 0.52553(17) 0.81927(16) 0.12439(16) 0.0275(3) Uani 1 1 d . . . C17 C 0.45437(18) 0.78206(19) -0.02936(17) 0.0353(4) Uani 1 1 d . . . H17A H 0.5238 0.8360 -0.0803 0.053 Uiso 1 1 calc R . . H17B H 0.3485 0.8131 -0.0236 0.053 Uiso 1 1 calc R . . H17C H 0.4439 0.6726 -0.0854 0.053 Uiso 1 1 calc R . . O1 O 0.89032(11) 1.16842(11) 0.36301(11) 0.0268(2) Uani 1 1 d . . . O2 O 1.02147(15) 1.34375(12) 0.63784(13) 0.0465(3) Uani 1 1 d . . . O3 O 1.12571(12) 1.37903(11) 0.90252(11) 0.0334(3) Uani 1 1 d . . . O4 O 0.79225(13) 0.92756(13) 0.85870(12) 0.0392(3) Uani 1 1 d . . . O5 O 0.60087(11) 0.76976(11) 0.61173(11) 0.0290(3) Uani 1 1 d . . . O6 O 0.43689(12) 0.73978(12) 0.19661(11) 0.0333(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 0.0206(6) 0.0207(6) 0.0249(6) 0.0113(5) 0.0054(5) 0.0041(5) C2 0.0206(6) 0.0200(6) 0.0243(7) 0.0077(5) 0.0020(5) 0.0027(5) C3 0.0276(7) 0.0228(7) 0.0270(7) 0.0096(6) 0.0022(6) 0.0018(6) C4 0.0212(6) 0.0244(7) 0.0277(7) 0.0059(6) -0.0017(5) 0.0027(5) C5 0.0291(7) 0.0318(8) 0.0230(7) 0.0094(6) -0.0020(6) 0.0025(6) C6 0.0264(7) 0.0291(7) 0.0248(7) 0.0111(6) 0.0040(6) 0.0028(6) C7 0.0222(6) 0.0217(6) 0.0227(6) 0.0086(5) 0.0025(5) 0.0045(5) C8 0.0218(6) 0.0216(6) 0.0272(7) 0.0111(6) 0.0047(5) 0.0023(5) C9 0.0231(6) 0.0209(6) 0.0259(7) 0.0078(6) 0.0007(5) 0.0026(5) C10 0.0223(6) 0.0222(7) 0.0242(7) 0.0089(5) 0.0026(5) 0.0047(5) C11 0.0393(9) 0.0368(9) 0.0582(11) 0.0310(8) -0.0033(8) 0.0042(7) C12 0.0408(8) 0.0340(8) 0.0315(8) 0.0051(7) -0.0126(7) -0.0021(7) C13 0.0498(10) 0.0278(8) 0.0428(9) 0.0192(7) 0.0034(8) 0.0042(7) C14 0.0361(8) 0.0275(7) 0.0293(7) 0.0111(6) -0.0043(6) -0.0046(6) C15 0.0278(7) 0.0261(7) 0.0245(7) 0.0109(6) 0.0017(5) 0.0031(6) C16 0.0271(7) 0.0288(7) 0.0267(7) 0.0099(6) 0.0024(6) 0.0052(6) C17 0.0318(8) 0.0408(9) 0.0297(8) 0.0100(7) -0.0029(6) 0.0033(7) O1 0.0282(5) 0.0266(5) 0.0281(5) 0.0147(4) 0.0030(4) 0.0004(4) O2 0.0654(8) 0.0329(6) 0.0357(6) 0.0167(5) -0.0119(6) -0.0193(6) O3 0.0349(5) 0.0283(5) 0.0314(6) 0.0085(5) -0.0080(4) -0.0049(4) O4 0.0476(7) 0.0415(6) 0.0291(6) 0.0200(5) -0.0028(5) -0.0098(5) O5 0.0288(5) 0.0278(5) 0.0332(6) 0.0170(4) 0.0023(4) -0.0021(4) O6 0.0309(5) 0.0354(6) 0.0301(5) 0.0125(5) -0.0049(4) -0.0061(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 O1 1.3734(15) . ? C1 C2 1.4027(19) . ? C1 C10 1.4051(18) . ? C2 C7 1.4181(19) . ? C2 C3 1.4926(18) . ? C3 O2 1.2105(17) . ? C3 C4 1.492(2) . ? C4 C5 1.335(2) . ? C4 O3 1.3456(16) . ? C5 C6 1.4569(19) . ? C5 H5 0.9500 . ? C6 O4 1.2209(17) . ? C6 C7 1.4932(19) . ? C7 C8 1.4025(18) . ? C8 O5 1.3742(16) . ? C8 C9 1.3863(19) . ? C9 C10 1.3874(19) . ? C9 C14 1.5088(18) . ? C10 C15 1.4553(18) . ? C11 O1 1.4360(19) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 O3 1.4392(18) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 O5 1.4318(18) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 O6 1.4322(18) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.3391(19) . ? C15 H15 0.9500 . ? C16 O6 1.3667(17) . ? C16 C17 1.488(2) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? 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 C2 122.15(11) . . ? O1 C1 C10 117.14(12) . . ? C2 C1 C10 120.49(12) . . ? C1 C2 C7 119.87(12) . . ? C1 C2 C3 120.59(12) . . ? C7 C2 C3 119.54(12) . . ? O2 C3 C4 118.76(12) . . ? O2 C3 C2 123.71(13) . . ? C4 C3 C2 117.51(12) . . ? C5 C4 O3 126.44(13) . . ? C5 C4 C3 122.16(12) . . ? O3 C4 C3 111.39(12) . . ? C4 C5 C6 122.05(13) . . ? C4 C5 H5 119.0 . . ? C6 C5 H5 119.0 . . ? O4 C6 C5 118.76(13) . . ? O4 C6 C7 122.70(12) . . ? C5 C6 C7 118.54(12) . . ? C8 C7 C2 118.73(12) . . ? C8 C7 C6 121.23(12) . . ? C2 C7 C6 120.02(12) . . ? O5 C8 C9 117.13(11) . . ? O5 C8 C7 122.45(12) . . ? C9 C8 C7 120.41(12) . . ? C8 C9 C10 121.55(12) . . ? C8 C9 C14 120.85(12) . . ? C10 C9 C14 117.38(12) . . ? C9 C10 C1 118.87(12) . . ? C9 C10 C15 117.89(12) . . ? C1 C10 C15 123.24(12) . . ? O1 C11 H11A 109.5 . . ? O1 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? O1 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? O3 C12 H12A 109.5 . . ? O3 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? O3 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? O5 C13 H13A 109.5 . . ? O5 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? O5 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? O6 C14 C9 112.87(12) . . ? O6 C14 H14A 109.0 . . ? C9 C14 H14A 109.0 . . ? O6 C14 H14B 109.0 . . ? C9 C14 H14B 109.0 . . ? H14A C14 H14B 107.8 . . ? C16 C15 C10 120.03(13) . . ? C16 C15 H15 120.0 . . ? C10 C15 H15 120.0 . . ? C15 C16 O6 122.01(13) . . ? C15 C16 C17 126.53(14) . . ? O6 C16 C17 111.38(12) . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C1 O1 C11 114.85(11) . . ? C4 O3 C12 116.00(12) . . ? C8 O5 C13 113.75(11) . . ? C16 O6 C14 115.51(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 O1 C1 C2 C7 -171.86(11) . . . . ? C10 C1 C2 C7 2.6(2) . . . . ? O1 C1 C2 C3 8.1(2) . . . . ? C10 C1 C2 C3 -177.50(12) . . . . ? C1 C2 C3 O2 6.6(2) . . . . ? C7 C2 C3 O2 -173.48(14) . . . . ? C1 C2 C3 C4 -175.07(12) . . . . ? C7 C2 C3 C4 4.85(19) . . . . ? O2 C3 C4 C5 175.25(14) . . . . ? C2 C3 C4 C5 -3.2(2) . . . . ? O2 C3 C4 O3 -4.20(19) . . . . ? C2 C3 C4 O3 177.38(11) . . . . ? O3 C4 C5 C6 -179.57(13) . . . . ? C3 C4 C5 C6 1.1(2) . . . . ? C4 C5 C6 O4 178.71(14) . . . . ? C4 C5 C6 C7 -0.5(2) . . . . ? C1 C2 C7 C8 -3.19(19) . . . . ? C3 C2 C7 C8 176.89(12) . . . . ? C1 C2 C7 C6 175.42(12) . . . . ? C3 C2 C7 C6 -4.50(19) . . . . ? O4 C6 C7 C8 1.7(2) . . . . ? C5 C6 C7 C8 -179.10(12) . . . . ? O4 C6 C7 C2 -176.89(13) . . . . ? C5 C6 C7 C2 2.32(19) . . . . ? C2 C7 C8 O5 -177.72(11) . . . . ? C6 C7 C8 O5 3.7(2) . . . . ? C2 C7 C8 C9 1.6(2) . . . . ? C6 C7 C8 C9 -176.97(12) . . . . ? O5 C8 C9 C10 179.99(11) . . . . ? C7 C8 C9 C10 0.6(2) . . . . ? O5 C8 C9 C14 -5.57(19) . . . . ? C7 C8 C9 C14 175.05(12) . . . . ? C8 C9 C10 C1 -1.3(2) . . . . ? C14 C9 C10 C1 -175.89(12) . . . . ? C8 C9 C10 C15 178.38(12) . . . . ? C14 C9 C10 C15 3.76(19) . . . . ? O1 C1 C10 C9 174.37(11) . . . . ? C2 C1 C10 C9 -0.3(2) . . . . ? O1 C1 C10 C15 -5.26(19) . . . . ? C2 C1 C10 C15 -179.97(12) . . . . ? C8 C9 C14 O6 153.50(13) . . . . ? C10 C9 C14 O6 -31.84(18) . . . . ? C9 C10 C15 C16 13.9(2) . . . . ? C1 C10 C15 C16 -166.46(13) . . . . ? C10 C15 C16 O6 -1.4(2) . . . . ? C10 C15 C16 C17 175.08(13) . . . . ? C2 C1 O1 C11 -92.92(15) . . . . ? C10 C1 O1 C11 92.46(15) . . . . ? C5 C4 O3 C12 -3.5(2) . . . . ? C3 C4 O3 C12 175.90(12) . . . . ? C9 C8 O5 C13 93.52(15) . . . . ? C7 C8 O5 C13 -87.12(16) . . . . ? C15 C16 O6 C14 -28.69(19) . . . . ? C17 C16 O6 C14 154.31(13) . . . . ? C9 C14 O6 C16 44.03(17) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.346 _refine_diff_density_min -0.222 _refine_diff_density_rms 0.049 #============================================================================== # End of file #==============================================================================