# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Dr Andrew Hughes' _publ_contact_author_email tahughes@optusnet.com.au _publ_section_title ; Synthesis of 1,2,3-Triazole linked Galactopyranosides and Evaluation of Cholera Toxin Inhibition ; loop_ _publ_author_name A.Hughes D.Leaver J.White A.Polyzos R.Dawson # Attachment '- Fig3a.cif' data_jmwah60 _database_code_depnum_ccdc_archive 'CCDC 833575' #TrackingRef '- Fig3a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H20 O9' _chemical_formula_weight 356.32 _chemical_oxdiff_usercomment 'DL-2-145-05 A Hughes/D Leaver' _chemical_absolute_configuration syn 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 21 21 21' _symmetry_cell_setting orthorhombic loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 7.1296(2) _cell_length_b 9.0495(4) _cell_length_c 27.5442(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1777.13(11) _cell_formula_units_Z 4 _cell_measurement_temperature 130.0 _cell_measurement_reflns_used 6305 _cell_measurement_theta_min 3.2013 _cell_measurement_theta_max 76.8860 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.5255 _exptl_crystal_size_mid 0.2722 _exptl_crystal_size_min 0.1771 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.332 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_absorpt_coefficient_mu 0.943 _exptl_absorpt_correction_T_min 0.706 _exptl_absorpt_correction_T_max 0.858 _exptl_absorpt_correction_type gaussian _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) Numerical absorption correction based on gaussian integration over a multifaceted crystal model ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 130.0 _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'SuperNova (Cu) 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 7003 _diffrn_reflns_av_R_equivalents 0.0123 _diffrn_reflns_av_sigmaI/netI 0.0153 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 3.21 _diffrn_reflns_theta_max 77.35 _reflns_number_total 3448 _reflns_number_gt 3402 _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^)+(0.0529P)^2^+0.6243P] 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 0.04(16) _refine_ls_number_reflns 3448 _refine_ls_number_parameters 235 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0365 _refine_ls_R_factor_gt 0.0360 _refine_ls_wR_factor_ref 0.0961 _refine_ls_wR_factor_gt 0.0956 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _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 O1 O 0.96517(15) 0.80095(12) 0.69991(4) 0.0218(2) Uani 1 1 d . . . O4 O 0.88577(16) 0.60781(12) 0.61862(4) 0.0227(2) Uani 1 1 d . A . O2 O 1.13813(16) 1.02692(12) 0.59808(5) 0.0240(3) Uani 1 1 d . . . O3 O 0.89363(18) 0.82156(13) 0.55171(4) 0.0266(3) Uani 1 1 d . . . O5 O 0.51779(16) 0.62086(13) 0.69741(5) 0.0286(3) Uani 1 1 d . . . O9 O 0.52598(19) 0.39618(15) 0.73052(6) 0.0409(4) Uani 1 1 d . . . O6 O 1.42999(18) 0.95669(17) 0.61759(7) 0.0444(4) Uani 1 1 d . . . C5 C 0.7794(2) 0.77276(17) 0.68252(6) 0.0208(3) Uani 1 1 d . . . H5 H 0.7011 0.8597 0.6888 0.025 Uiso 1 1 calc R . . O7 O 0.7633(3) 1.0312(2) 0.52344(6) 0.0548(5) Uani 1 1 d . . . C3 C 0.8735(2) 0.86751(17) 0.60134(6) 0.0206(3) Uani 1 1 d . . . H3 H 0.7953 0.9564 0.6031 0.025 Uiso 1 1 calc R . . C4 C 0.7792(2) 0.74106(16) 0.62855(6) 0.0208(3) Uani 1 1 d . . . H4 H 0.6500 0.7291 0.6171 0.025 Uiso 1 1 calc R . . C1 C 1.0496(2) 0.92718(17) 0.67750(6) 0.0214(3) Uani 1 1 d . . . H1 H 1.1766 0.9382 0.6906 0.026 Uiso 1 1 calc R . . C6 C 0.7086(2) 0.64506(18) 0.71286(7) 0.0243(3) Uani 1 1 d . . . H6A H 0.7840 0.5575 0.7073 0.029 Uiso 1 1 calc R . . H6B H 0.7130 0.6695 0.7471 0.029 Uiso 1 1 calc R . . C15 C 0.9430(2) 1.06327(17) 0.68890(6) 0.0229(3) Uani 1 1 d . . . C2 C 1.0654(2) 0.89888(17) 0.62278(6) 0.0206(3) Uani 1 1 d . . . H2 H 1.1483 0.8143 0.6170 0.025 Uiso 1 1 calc R . . C14 C 0.2505(3) 0.4762(2) 0.68708(8) 0.0344(4) Uani 1 1 d . . . H14A H 0.2184 0.5659 0.6704 0.052 Uiso 0.50 1 calc PR . . H14B H 0.1627 0.4593 0.7129 0.052 Uiso 0.50 1 calc PR . . H14C H 0.2462 0.3949 0.6647 0.052 Uiso 0.50 1 calc PR . . H14D H 0.1998 0.3808 0.6949 0.052 Uiso 0.50 1 calc PR . . H14E H 0.2555 0.4874 0.6524 0.052 Uiso 0.50 1 calc PR . . H14F H 0.1721 0.5518 0.7007 0.052 Uiso 0.50 1 calc PR . . C16 C 0.8504(3) 1.16637(19) 0.69984(7) 0.0299(4) Uani 1 1 d . . . H16 H 0.7775 1.2475 0.7085 0.036 Uiso 1 1 calc R . . C8 C 1.3835(3) 1.1778(2) 0.57017(10) 0.0461(6) Uani 1 1 d . . . H8A H 1.2732 1.2261 0.5580 0.069 Uiso 1 1 calc R . . H8B H 1.4628 1.1503 0.5435 0.069 Uiso 1 1 calc R . . H8C H 1.4501 1.2438 0.5913 0.069 Uiso 1 1 calc R . . C13 C 0.4434(2) 0.48920(18) 0.70755(7) 0.0260(4) Uani 1 1 d . . . C12 C 0.9283(3) 0.3747(2) 0.58269(8) 0.0359(4) Uani 1 1 d . A . H12A H 0.8595 0.2951 0.5681 0.054 Uiso 0.50 1 calc PR . . H12B H 0.9948 0.3388 0.6106 0.054 Uiso 0.50 1 calc PR . . H12C H 1.0161 0.4139 0.5596 0.054 Uiso 0.50 1 calc PR . . H12D H 1.0541 0.4034 0.5908 0.054 Uiso 0.50 1 calc PR . . H12E H 0.9188 0.3598 0.5483 0.054 Uiso 0.50 1 calc PR . . H12F H 0.8975 0.2846 0.5993 0.054 Uiso 0.50 1 calc PR . . C11 C 0.7954(3) 0.4934(2) 0.59786(9) 0.0402(5) Uani 1 1 d . . . O8 O 0.6251(3) 0.4862(2) 0.59716(12) 0.0562(7) Uani 0.80 1 d PU A 1 O8' O 0.6769(13) 0.5307(11) 0.5625(4) 0.057(3) Uani 0.20 1 d PU A 2 C7 C 1.3278(2) 1.04223(19) 0.59781(8) 0.0293(4) Uani 1 1 d . . . C9 C 0.8228(3) 0.9083(2) 0.51628(7) 0.0312(4) Uani 1 1 d . . . C10 C 0.8335(3) 0.8309(3) 0.46872(7) 0.0457(5) Uani 1 1 d . . . H10A H 0.8864 0.7344 0.4733 0.069 Uiso 0.50 1 calc PR . . H10B H 0.9111 0.8867 0.4469 0.069 Uiso 0.50 1 calc PR . . H10C H 0.7098 0.8218 0.4553 0.069 Uiso 0.50 1 calc PR . . H10D H 0.7852 0.8942 0.4437 0.069 Uiso 0.50 1 calc PR . . H10E H 0.7604 0.7419 0.4701 0.069 Uiso 0.50 1 calc PR . . H10F H 0.9618 0.8067 0.4617 0.069 Uiso 0.50 1 calc PR . . 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 0.0196(5) 0.0223(5) 0.0234(6) 0.0027(4) -0.0045(4) -0.0016(4) O4 0.0216(5) 0.0174(5) 0.0290(7) -0.0038(4) -0.0028(4) 0.0021(4) O2 0.0199(5) 0.0221(5) 0.0301(7) 0.0023(5) 0.0041(5) 0.0011(4) O3 0.0343(6) 0.0261(5) 0.0193(6) -0.0037(5) -0.0023(5) 0.0027(5) O5 0.0201(5) 0.0250(6) 0.0406(8) 0.0094(5) -0.0026(5) -0.0022(4) O9 0.0270(6) 0.0290(7) 0.0666(10) 0.0166(7) 0.0044(6) -0.0012(5) O6 0.0202(6) 0.0408(8) 0.0721(11) 0.0121(7) 0.0002(6) 0.0022(6) C5 0.0181(7) 0.0181(7) 0.0263(9) -0.0001(6) -0.0017(6) 0.0022(5) O7 0.0691(11) 0.0608(11) 0.0344(9) 0.0098(7) 0.0022(8) 0.0324(9) C3 0.0207(7) 0.0205(7) 0.0208(8) -0.0025(6) -0.0016(6) 0.0021(6) C4 0.0171(7) 0.0176(7) 0.0277(9) -0.0012(6) -0.0036(6) 0.0020(5) C1 0.0200(7) 0.0200(7) 0.0244(9) -0.0005(6) -0.0018(6) -0.0013(6) C6 0.0194(7) 0.0228(7) 0.0308(9) 0.0048(6) -0.0012(6) 0.0004(6) C15 0.0265(8) 0.0218(7) 0.0203(8) -0.0023(6) -0.0006(6) -0.0047(6) C2 0.0190(7) 0.0190(7) 0.0237(8) 0.0003(6) 0.0006(6) 0.0002(6) C14 0.0276(9) 0.0381(10) 0.0375(11) -0.0007(8) 0.0016(8) -0.0064(8) C16 0.0351(9) 0.0237(7) 0.0309(10) -0.0026(7) 0.0018(7) 0.0001(7) C8 0.0293(9) 0.0327(9) 0.0762(17) 0.0078(10) 0.0205(10) -0.0016(8) C13 0.0216(7) 0.0241(8) 0.0323(10) -0.0003(7) 0.0074(7) -0.0005(6) C12 0.0423(10) 0.0230(8) 0.0423(12) -0.0093(7) -0.0050(9) 0.0020(8) C11 0.0334(10) 0.0275(9) 0.0598(14) -0.0127(9) -0.0132(9) 0.0028(8) O8 0.0299(10) 0.0343(10) 0.104(2) -0.0288(12) -0.0088(12) -0.0027(8) O8' 0.041(5) 0.054(5) 0.074(7) -0.038(5) -0.036(5) 0.018(4) C7 0.0192(7) 0.0246(8) 0.0439(11) -0.0019(7) 0.0070(7) 0.0008(6) C9 0.0249(8) 0.0464(11) 0.0224(9) 0.0039(8) -0.0001(6) 0.0025(8) C10 0.0461(12) 0.0681(14) 0.0229(10) -0.0050(10) -0.0024(8) -0.0088(11) _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 C1 1.4310(19) . ? O1 C5 1.4312(18) . ? O4 C11 1.347(2) . ? O4 C4 1.4514(17) . ? O2 C7 1.359(2) . ? O2 C2 1.4402(19) . ? O3 C9 1.350(2) . ? O3 C3 1.436(2) . ? O5 C13 1.334(2) . ? O5 C6 1.4422(19) . ? O9 C13 1.206(2) . ? O6 C7 1.195(2) . ? C5 C6 1.513(2) . ? C5 C4 1.514(2) . ? O7 C9 1.207(3) . ? C3 C2 1.517(2) . ? C3 C4 1.524(2) . ? C1 C15 1.481(2) . ? C1 C2 1.533(2) . ? C15 C16 1.182(2) . ? C14 C13 1.491(2) . ? C8 C7 1.497(3) . ? C12 C11 1.492(3) . ? C11 O8 1.216(3) . ? C11 O8' 1.333(9) . ? C9 C10 1.487(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 C5 112.77(12) . . ? C11 O4 C4 117.91(13) . . ? C7 O2 C2 116.28(13) . . ? C9 O3 C3 118.85(13) . . ? C13 O5 C6 116.67(13) . . ? O1 C5 C6 105.07(12) . . ? O1 C5 C4 111.31(13) . . ? C6 C5 C4 113.41(13) . . ? O3 C3 C2 109.56(13) . . ? O3 C3 C4 107.14(12) . . ? C2 C3 C4 110.31(13) . . ? O4 C4 C5 109.99(12) . . ? O4 C4 C3 107.45(12) . . ? C5 C4 C3 109.87(12) . . ? O1 C1 C15 110.91(13) . . ? O1 C1 C2 108.76(12) . . ? C15 C1 C2 112.66(13) . . ? O5 C6 C5 105.53(13) . . ? C16 C15 C1 175.65(18) . . ? O2 C2 C3 106.94(13) . . ? O2 C2 C1 110.88(13) . . ? C3 C2 C1 110.35(13) . . ? O9 C13 O5 122.63(16) . . ? O9 C13 C14 126.38(17) . . ? O5 C13 C14 110.99(15) . . ? O8 C11 O8' 50.9(5) . . ? O8 C11 O4 121.73(19) . . ? O8' C11 O4 114.8(4) . . ? O8 C11 C12 126.21(19) . . ? O8' C11 C12 112.4(4) . . ? O4 C11 C12 111.62(16) . . ? O6 C7 O2 122.57(17) . . ? O6 C7 C8 126.93(17) . . ? O2 C7 C8 110.50(16) . . ? O7 C9 O3 123.30(18) . . ? O7 C9 C10 126.56(19) . . ? O3 C9 C10 110.13(17) . . ? _diffrn_measured_fraction_theta_max 0.950 _diffrn_reflns_theta_full 67.50 _diffrn_measured_fraction_theta_full 0.963 _refine_diff_density_max 0.489 _refine_diff_density_min -0.328 _refine_diff_density_rms 0.045 # Attachment '- Fig3b.cif' data_jmwah61 _database_code_depnum_ccdc_archive 'CCDC 833576' #TrackingRef '- Fig3b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H20 O9' _chemical_formula_weight 356.32 _chemical_oxdiff_usercomment 'D lEAVER dl-Z-167-07' _chemical_absolute_configuration rm 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_space_group_name_H-M 'C 1 2 1' _symmetry_cell_setting monoclinic 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' _cell_length_a 18.1428(8) _cell_length_b 8.3337(5) _cell_length_c 11.7816(9) _cell_angle_alpha 90.00 _cell_angle_beta 94.391(6) _cell_angle_gamma 90.00 _cell_volume 1776.11(19) _cell_formula_units_Z 4 _cell_measurement_temperature 130.0 _cell_measurement_reflns_used 2149 _cell_measurement_theta_min 2.9394 _cell_measurement_theta_max 29.1297 _exptl_crystal_description slab _exptl_crystal_colour colourless _exptl_crystal_size_max 0.6030 _exptl_crystal_size_mid 0.3113 _exptl_crystal_size_min 0.1116 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.333 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_absorpt_coefficient_mu 0.110 _exptl_absorpt_correction_T_min 0.83656 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) 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 4376 _diffrn_reflns_av_R_equivalents 0.0260 _diffrn_reflns_av_sigmaI/netI 0.0385 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.95 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2620 _reflns_number_gt 2378 _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^)+(0.0378P)^2^+0.8436P] 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 -0.6(12) _refine_ls_number_reflns 2620 _refine_ls_number_parameters 230 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0438 _refine_ls_R_factor_gt 0.0374 _refine_ls_wR_factor_ref 0.0906 _refine_ls_wR_factor_gt 0.0861 _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 O2 O 0.31807(9) -0.0714(2) 1.27676(14) 0.0265(4) Uani 1 1 d . . . O3 O 0.15981(9) -0.0639(2) 1.27087(13) 0.0242(4) Uani 1 1 d . . . O4 O 0.13200(9) 0.1292(2) 1.08287(14) 0.0267(4) Uani 1 1 d . . . O1 O 0.26601(8) 0.0640(2) 0.98737(14) 0.0219(4) Uani 1 1 d . . . O5 O 0.21144(10) 0.0051(2) 0.76789(14) 0.0330(5) Uani 1 1 d . . . O6 O 0.33588(11) 0.1644(2) 1.36778(16) 0.0392(5) Uani 1 1 d . . . O8 O 0.02068(11) 0.0426(3) 1.13304(17) 0.0472(6) Uani 1 1 d . . . O9 O 0.11789(12) 0.0587(3) 0.63876(16) 0.0451(5) Uani 1 1 d . . . O7 O 0.10010(10) -0.2977(2) 1.23916(17) 0.0364(5) Uani 1 1 d . . . C1 C 0.31198(13) -0.0017(3) 1.0791(2) 0.0224(6) Uani 1 1 d . . . H1 H 0.3228 -0.1138 1.0614 0.027 Uiso 1 1 calc R . . C3 C 0.19992(13) -0.0914(3) 1.1714(2) 0.0223(6) Uani 1 1 d . . . H3 H 0.2111 -0.2059 1.1647 0.027 Uiso 1 1 calc R . . C5 C 0.20156(13) -0.0348(3) 0.9642(2) 0.0211(5) Uani 1 1 d . . . H5 H 0.2179 -0.1451 0.9521 0.025 Uiso 1 1 calc R . . C2 C 0.27088(13) 0.0032(3) 1.1884(2) 0.0217(6) Uani 1 1 d . . . H2 H 0.2604 0.1144 1.2088 0.026 Uiso 1 1 calc R . . C6 C 0.16143(13) 0.0238(3) 0.8560(2) 0.0243(6) Uani 1 1 d . . . H6A H 0.1169 -0.0387 0.8384 0.029 Uiso 1 1 calc R . . H6B H 0.1477 0.1356 0.8633 0.029 Uiso 1 1 calc R . . C8 C 0.43878(14) 0.1549(3) 1.1099(2) 0.0302(6) Uani 1 1 d . . . H8 H 0.4837 0.2080 1.1235 0.036 Uiso 1 1 calc R . . C9 C 0.35056(14) 0.0256(4) 1.3584(2) 0.0301(6) Uani 1 1 d . . . C11 C 0.10770(14) -0.1750(3) 1.2925(2) 0.0275(6) Uani 1 1 d . . . C4 C 0.15471(13) -0.0340(3) 1.0644(2) 0.0221(6) Uani 1 1 d . . . H4 H 0.1113 -0.1027 1.0488 0.026 Uiso 1 1 calc R . . C12 C 0.06360(16) -0.1249(4) 1.3879(2) 0.0397(8) Uani 1 1 d . . . H12A H 0.0155 -0.1735 1.3788 0.060 Uiso 1 1 calc R . . H12B H 0.0585 -0.0102 1.3876 0.060 Uiso 1 1 calc R . . H12C H 0.0883 -0.1586 1.4589 0.060 Uiso 1 1 calc R . . C15 C 0.18159(17) 0.0281(4) 0.6605(2) 0.0364(7) Uani 1 1 d . . . C7 C 0.38143(14) 0.0870(3) 1.0925(2) 0.0252(6) Uani 1 1 d . . . C10 C 0.40669(17) -0.0633(5) 1.4322(3) 0.0534(9) Uani 1 1 d . . . H10A H 0.4512 -0.0741 1.3936 0.080 Uiso 1 1 calc R . . H10B H 0.3880 -0.1678 1.4487 0.080 Uiso 1 1 calc R . . H10C H 0.4172 -0.0053 1.5020 0.080 Uiso 1 1 calc R . . C16 C 0.2385(2) 0.0085(5) 0.5779(2) 0.0574(11) Uani 1 1 d . . . H16A H 0.2184 0.0402 0.5035 0.086 Uiso 1 1 calc R . . H16B H 0.2536 -0.1019 0.5761 0.086 Uiso 1 1 calc R . . H16C H 0.2805 0.0744 0.6004 0.086 Uiso 1 1 calc R . . C13 C 0.06399(17) 0.1510(4) 1.1229(2) 0.0375(7) Uani 1 1 d . . . C14 C 0.0529(3) 0.3219(5) 1.1523(4) 0.0752(14) Uani 1 1 d . . . H14A H 0.0075 0.3332 1.1881 0.113 Uiso 1 1 calc R . . H14B H 0.0509 0.3856 1.0842 0.113 Uiso 1 1 calc R . . H14C H 0.0933 0.3575 1.2035 0.113 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 O2 0.0237(9) 0.0273(10) 0.0271(10) 0.0028(8) -0.0082(7) 0.0009(9) O3 0.0233(9) 0.0292(10) 0.0200(9) -0.0019(8) 0.0005(7) -0.0017(9) O4 0.0272(9) 0.0270(10) 0.0258(10) -0.0008(7) 0.0017(8) 0.0080(8) O1 0.0195(8) 0.0205(9) 0.0251(9) 0.0004(7) -0.0015(7) -0.0033(8) O5 0.0299(10) 0.0478(13) 0.0214(9) -0.0021(8) 0.0032(7) -0.0103(9) O6 0.0454(12) 0.0362(13) 0.0344(12) -0.0071(9) -0.0068(9) -0.0048(11) O8 0.0257(10) 0.0773(17) 0.0391(12) 0.0049(12) 0.0055(9) 0.0071(13) O9 0.0514(13) 0.0526(14) 0.0293(11) 0.0029(10) -0.0094(9) -0.0050(12) O7 0.0319(10) 0.0352(12) 0.0426(12) -0.0034(10) 0.0053(9) -0.0105(10) C1 0.0179(12) 0.0198(14) 0.0291(14) 0.0001(11) -0.0010(10) 0.0015(11) C3 0.0233(12) 0.0235(15) 0.0204(13) -0.0004(11) 0.0026(10) -0.0007(12) C5 0.0194(12) 0.0205(13) 0.0233(13) -0.0036(10) 0.0016(10) -0.0075(11) C2 0.0192(12) 0.0210(14) 0.0240(13) 0.0020(11) -0.0048(10) 0.0018(11) C6 0.0244(13) 0.0271(15) 0.0214(12) -0.0024(11) 0.0013(10) -0.0042(12) C8 0.0213(13) 0.0307(16) 0.0383(16) -0.0005(12) 0.0004(11) -0.0006(13) C9 0.0257(14) 0.0361(19) 0.0277(14) -0.0004(13) -0.0033(11) -0.0045(14) C11 0.0196(13) 0.0367(18) 0.0256(15) 0.0058(13) -0.0023(11) -0.0041(13) C4 0.0211(12) 0.0217(14) 0.0229(13) -0.0026(10) -0.0012(10) -0.0003(11) C12 0.0376(16) 0.053(2) 0.0299(17) 0.0047(14) 0.0089(13) -0.0018(15) C15 0.0444(17) 0.0387(18) 0.0259(15) -0.0013(13) 0.0010(13) -0.0211(16) C7 0.0229(14) 0.0250(15) 0.0274(14) 0.0006(11) 0.0007(11) 0.0052(12) C10 0.0435(18) 0.063(2) 0.049(2) -0.0078(18) -0.0251(15) 0.0066(19) C16 0.060(2) 0.087(3) 0.0262(16) -0.0049(17) 0.0108(14) -0.032(2) C13 0.0351(16) 0.055(2) 0.0228(14) 0.0081(14) 0.0034(12) 0.0209(17) C14 0.093(3) 0.065(3) 0.073(3) 0.020(2) 0.040(2) 0.052(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 O2 C9 1.356(3) . ? O2 C2 1.438(3) . ? O3 C11 1.362(3) . ? O3 C3 1.444(3) . ? O4 C13 1.366(3) . ? O4 C4 1.442(3) . ? O1 C1 1.423(3) . ? O1 C5 1.439(3) . ? O5 C15 1.351(3) . ? O5 C6 1.438(3) . ? O6 C9 1.195(3) . ? O8 C13 1.209(4) . ? O9 C15 1.192(3) . ? O7 C11 1.202(3) . ? C1 C7 1.459(4) . ? C1 C2 1.537(3) . ? C1 H1 0.9800 . ? C3 C2 1.510(3) . ? C3 C4 1.527(3) . ? C3 H3 0.9800 . ? C5 C6 1.501(3) . ? C5 C4 1.506(3) . ? C5 H5 0.9800 . ? C2 H2 0.9800 . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C8 C7 1.188(4) . ? C8 H8 0.9300 . ? C9 C10 1.485(4) . ? C11 C12 1.488(4) . ? C4 H4 0.9800 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C15 C16 1.482(4) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C13 C14 1.483(5) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 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 O2 C2 117.3(2) . . ? C11 O3 C3 116.4(2) . . ? C13 O4 C4 117.0(2) . . ? C1 O1 C5 110.12(18) . . ? C15 O5 C6 115.5(2) . . ? O1 C1 C7 109.8(2) . . ? O1 C1 C2 109.39(18) . . ? C7 C1 C2 111.4(2) . . ? O1 C1 H1 108.7 . . ? C7 C1 H1 108.7 . . ? C2 C1 H1 108.7 . . ? O3 C3 C2 106.69(19) . . ? O3 C3 C4 110.35(19) . . ? C2 C3 C4 110.1(2) . . ? O3 C3 H3 109.9 . . ? C2 C3 H3 109.9 . . ? C4 C3 H3 109.9 . . ? O1 C5 C6 108.01(19) . . ? O1 C5 C4 110.39(19) . . ? C6 C5 C4 113.5(2) . . ? O1 C5 H5 108.3 . . ? C6 C5 H5 108.3 . . ? C4 C5 H5 108.3 . . ? O2 C2 C3 108.9(2) . . ? O2 C2 C1 107.15(19) . . ? C3 C2 C1 109.78(19) . . ? O2 C2 H2 110.3 . . ? C3 C2 H2 110.3 . . ? C1 C2 H2 110.3 . . ? O5 C6 C5 106.6(2) . . ? O5 C6 H6A 110.4 . . ? C5 C6 H6A 110.4 . . ? O5 C6 H6B 110.4 . . ? C5 C6 H6B 110.4 . . ? H6A C6 H6B 108.6 . . ? C7 C8 H8 180.0 . . ? O6 C9 O2 123.7(3) . . ? O6 C9 C10 125.2(3) . . ? O2 C9 C10 111.1(3) . . ? O7 C11 O3 122.3(2) . . ? O7 C11 C12 125.9(3) . . ? O3 C11 C12 111.8(2) . . ? O4 C4 C5 107.9(2) . . ? O4 C4 C3 108.2(2) . . ? C5 C4 C3 110.2(2) . . ? O4 C4 H4 110.2 . . ? C5 C4 H4 110.2 . . ? C3 C4 H4 110.2 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? O9 C15 O5 123.0(3) . . ? O9 C15 C16 126.6(3) . . ? O5 C15 C16 110.5(3) . . ? C8 C7 C1 175.9(3) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? 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 C13 O4 123.1(3) . . ? O8 C13 C14 126.4(3) . . ? O4 C13 C14 110.5(3) . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 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 C5 O1 C1 C7 172.8(2) . . . . ? C5 O1 C1 C2 -64.6(2) . . . . ? C11 O3 C3 C2 -158.81(19) . . . . ? C11 O3 C3 C4 81.5(3) . . . . ? C1 O1 C5 C6 -170.99(19) . . . . ? C1 O1 C5 C4 64.4(2) . . . . ? C9 O2 C2 C3 -133.3(2) . . . . ? C9 O2 C2 C1 108.0(2) . . . . ? O3 C3 C2 O2 70.5(2) . . . . ? C4 C3 C2 O2 -169.7(2) . . . . ? O3 C3 C2 C1 -172.49(18) . . . . ? C4 C3 C2 C1 -52.7(3) . . . . ? O1 C1 C2 O2 177.24(18) . . . . ? C7 C1 C2 O2 -61.2(2) . . . . ? O1 C1 C2 C3 59.1(2) . . . . ? C7 C1 C2 C3 -179.3(2) . . . . ? C15 O5 C6 C5 170.1(2) . . . . ? O1 C5 C6 O5 61.2(3) . . . . ? C4 C5 C6 O5 -176.03(19) . . . . ? C2 O2 C9 O6 8.6(4) . . . . ? C2 O2 C9 C10 -170.7(2) . . . . ? C3 O3 C11 O7 7.2(3) . . . . ? C3 O3 C11 C12 -173.0(2) . . . . ? C13 O4 C4 C5 146.9(2) . . . . ? C13 O4 C4 C3 -93.9(2) . . . . ? O1 C5 C4 O4 60.6(2) . . . . ? C6 C5 C4 O4 -60.8(3) . . . . ? O1 C5 C4 C3 -57.3(3) . . . . ? C6 C5 C4 C3 -178.7(2) . . . . ? O3 C3 C4 O4 52.0(2) . . . . ? C2 C3 C4 O4 -65.5(2) . . . . ? O3 C3 C4 C5 169.76(19) . . . . ? C2 C3 C4 C5 52.2(3) . . . . ? C6 O5 C15 O9 -1.4(4) . . . . ? C6 O5 C15 C16 179.0(3) . . . . ? O1 C1 C7 C8 166(4) . . . . ? C2 C1 C7 C8 44(4) . . . . ? C4 O4 C13 O8 -6.9(4) . . . . ? C4 O4 C13 C14 172.3(2) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.196 _refine_diff_density_min -0.176 _refine_diff_density_rms 0.041