data_189a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H24 O9' _chemical_formula_weight 396.38 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.3808(7) _cell_length_b 10.8134(9) _cell_length_c 11.1500(9) _cell_angle_alpha 75.083(2) _cell_angle_beta 88.217(2) _cell_angle_gamma 87.818(2) _cell_volume 975.47(14) _cell_formula_units_Z 2 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 2648 _cell_measurement_theta_min 2.4 _cell_measurement_theta_max 24.5 _exptl_crystal_description 'rectangular shape, cut' _exptl_crystal_colour orange _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.350 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 420 _exptl_absorpt_coefficient_mu 0.108 _exptl_absorpt_correction_type 'sadabs (Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.6663 _exptl_absorpt_correction_T_max 0.9828 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(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 ? _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 15063 _diffrn_reflns_av_R_equivalents 0.0556 _diffrn_reflns_av_sigmaI/netI 0.0525 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 30.01 _reflns_number_total 5639 _reflns_number_gt 4116 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker AXS, SMART' _computing_cell_refinement 'Bruker AXS, SAINT' _computing_data_reduction 'Bruker AXS, SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker AXS, SHELXTL' _computing_publication_material 'Bruker AXS, 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^)+(0.0600P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5639 _refine_ls_number_parameters 319 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0692 _refine_ls_R_factor_gt 0.0521 _refine_ls_wR_factor_ref 0.1227 _refine_ls_wR_factor_gt 0.1167 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.48796(12) 0.37368(10) 0.39973(9) 0.0364(2) Uani 1 1 d . . . H1 H 0.406(3) 0.3331(18) 0.4081(18) 0.060(6) Uiso 1 1 d . . . O2 O 0.74829(12) 0.49616(9) 0.43048(9) 0.0355(2) Uani 1 1 d . . . H2 H 0.840(2) 0.5249(18) 0.4469(18) 0.063(6) Uiso 1 1 d . . . O3 O 0.95178(11) 0.39279(9) 0.62126(9) 0.0338(2) Uani 1 1 d . . . H3 H 0.981(2) 0.3693(18) 0.702(2) 0.064(6) Uiso 1 1 d . . . O4 O 0.68598(13) -0.23497(9) 0.90960(8) 0.0372(2) Uani 1 1 d . . . H4 H 0.713(2) -0.3151(19) 0.9543(17) 0.051(5) Uiso 1 1 d . . . O5 O 0.44104(12) 0.13102(9) 0.90520(9) 0.0353(2) Uani 1 1 d . . . H5 H 0.381(2) 0.1519(16) 0.9672(17) 0.050(5) Uiso 1 1 d . . . C1 C 0.62526(14) 0.00992(11) 0.75810(11) 0.0224(2) Uani 1 1 d . . . H1A H 0.6710 0.0083 0.8393 0.022(3) Uiso 1 1 calc R . . C2 C 0.65215(14) 0.14330(10) 0.67384(10) 0.0227(2) Uani 1 1 d . . . C3 C 0.54973(14) 0.19908(11) 0.57844(11) 0.0253(3) Uani 1 1 d . . . H3A H 0.4565 0.1574 0.5686 0.033(4) Uiso 1 1 calc R . . C4 C 0.58414(14) 0.31615(11) 0.49743(11) 0.0255(3) Uani 1 1 d . . . C5 C 0.72023(14) 0.38013(11) 0.51121(11) 0.0258(3) Uani 1 1 d . . . C6 C 0.82102(14) 0.32480(11) 0.60883(11) 0.0250(3) Uani 1 1 d . . . C7 C 0.78854(14) 0.20704(11) 0.68870(11) 0.0242(2) Uani 1 1 d . . . H7 H 0.8588 0.1700 0.7532 0.022(3) Uiso 1 1 calc R . . C8 C 0.71635(14) -0.09328(11) 0.70995(11) 0.0238(2) Uani 1 1 d . . . C9 C 0.74301(15) -0.21444(12) 0.78993(11) 0.0267(3) Uani 1 1 d . . . C10 C 0.82581(16) -0.31055(12) 0.74938(13) 0.0319(3) Uani 1 1 d . . . H10 H 0.8426 -0.3917 0.8042 0.036(4) Uiso 1 1 calc R . . C11 C 0.88343(16) -0.28654(13) 0.62826(13) 0.0345(3) Uani 1 1 d . . . H11 H 0.9395 -0.3516 0.6010 0.036(4) Uiso 1 1 calc R . . C12 C 0.85911(16) -0.16800(14) 0.54746(13) 0.0346(3) Uani 1 1 d . . . H12 H 0.8980 -0.1518 0.4651 0.041(4) Uiso 1 1 calc R . . C13 C 0.77618(15) -0.07214(12) 0.58889(12) 0.0295(3) Uani 1 1 d . . . H13 H 0.7603 0.0089 0.5336 0.027(3) Uiso 1 1 calc R . . C14 C 0.44839(14) -0.01699(11) 0.78197(10) 0.0234(2) Uani 1 1 d . . . C15 C 0.36051(15) 0.04716(11) 0.85782(11) 0.0275(3) Uani 1 1 d . . . C16 C 0.19888(16) 0.02694(14) 0.88180(14) 0.0377(3) Uani 1 1 d . . . H16 H 0.1416 0.0704 0.9331 0.045(4) Uiso 1 1 calc R . . C17 C 0.12240(17) -0.05702(15) 0.83023(15) 0.0422(4) Uani 1 1 d . . . H17 H 0.0091(19) -0.0724(14) 0.8474(14) 0.038(4) Uiso 1 1 d . . . C18 C 0.20595(17) -0.12095(15) 0.75485(14) 0.0395(3) Uani 1 1 d . . . H18 H 0.1536 -0.1780 0.7196 0.039(4) Uiso 1 1 calc R . . C19 C 0.36818(16) -0.10058(12) 0.73129(12) 0.0308(3) Uani 1 1 d . . . H19 H 0.4246 -0.1445 0.6799 0.029(4) Uiso 1 1 calc R . . O1S O 0.74232(14) 0.53683(11) 0.06476(10) 0.0411(3) Uani 1 1 d . . . H1SA H 0.723(2) 0.467(2) 0.0445(19) 0.067(6) Uiso 1 1 d . . . H1SB H 0.662(2) 0.5406(19) 0.120(2) 0.065(6) Uiso 1 1 d . . . O2S O 1.01272(17) 0.33851(14) 0.85837(12) 0.0566(3) Uani 1 1 d . . . H2SA H 1.076(3) 0.387(2) 0.882(2) 0.087(8) Uiso 1 1 d . . . H2SB H 0.917(4) 0.342(2) 0.904(3) 0.104(9) Uiso 1 1 d . . . O3S O 0.50623(13) 0.60062(11) 0.21428(10) 0.0405(3) Uani 1 1 d . . . H3SA H 0.504(2) 0.533(2) 0.285(2) 0.066(6) Uiso 1 1 d . . . H3SB H 0.531(3) 0.669(2) 0.229(2) 0.077(7) Uiso 1 1 d . . . O4S O 0.71104(15) 0.32604(12) 0.97457(12) 0.0498(3) Uani 1 1 d . . . H4SA H 0.637(3) 0.350(2) 0.905(2) 0.096(8) Uiso 1 1 d . . . H4SB H 0.685(3) 0.255(3) 1.017(2) 0.087(8) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0312(5) 0.0371(5) 0.0341(5) 0.0049(4) -0.0095(4) -0.0073(4) O2 0.0333(5) 0.0309(5) 0.0359(5) 0.0047(4) -0.0019(4) -0.0090(4) O3 0.0316(5) 0.0361(5) 0.0319(5) -0.0030(4) -0.0027(4) -0.0148(4) O4 0.0571(6) 0.0264(5) 0.0250(5) -0.0029(4) 0.0063(4) 0.0062(4) O5 0.0416(5) 0.0316(5) 0.0361(5) -0.0158(4) 0.0118(4) -0.0066(4) C1 0.0252(6) 0.0218(5) 0.0204(5) -0.0057(4) 0.0006(4) -0.0027(4) C2 0.0253(6) 0.0216(5) 0.0218(5) -0.0071(4) 0.0027(4) -0.0020(4) C3 0.0241(6) 0.0263(6) 0.0257(6) -0.0064(5) 0.0002(5) -0.0056(5) C4 0.0248(6) 0.0281(6) 0.0227(6) -0.0048(5) -0.0010(5) 0.0001(5) C5 0.0269(6) 0.0232(6) 0.0259(6) -0.0042(5) 0.0047(5) -0.0030(5) C6 0.0226(6) 0.0279(6) 0.0263(6) -0.0100(5) 0.0026(5) -0.0051(5) C7 0.0239(6) 0.0259(6) 0.0231(6) -0.0066(5) -0.0014(4) -0.0009(4) C8 0.0230(6) 0.0251(6) 0.0247(6) -0.0090(5) -0.0005(4) -0.0026(4) C9 0.0280(6) 0.0285(6) 0.0252(6) -0.0097(5) 0.0005(5) -0.0023(5) C10 0.0337(7) 0.0255(6) 0.0375(7) -0.0103(5) -0.0006(5) 0.0014(5) C11 0.0294(7) 0.0380(7) 0.0424(8) -0.0226(6) 0.0035(6) 0.0008(5) C12 0.0333(7) 0.0435(8) 0.0301(7) -0.0159(6) 0.0057(5) -0.0019(6) C13 0.0315(6) 0.0318(7) 0.0252(6) -0.0070(5) 0.0009(5) -0.0017(5) C14 0.0257(6) 0.0217(5) 0.0204(5) -0.0008(4) 0.0002(4) -0.0020(4) C15 0.0317(6) 0.0233(6) 0.0255(6) -0.0028(5) 0.0022(5) -0.0010(5) C16 0.0307(7) 0.0398(8) 0.0393(8) -0.0058(6) 0.0072(6) 0.0034(6) C17 0.0260(7) 0.0505(9) 0.0450(9) -0.0024(7) 0.0006(6) -0.0056(6) C18 0.0339(7) 0.0462(8) 0.0381(8) -0.0076(6) -0.0071(6) -0.0127(6) C19 0.0330(7) 0.0324(7) 0.0274(6) -0.0079(5) -0.0016(5) -0.0055(5) O1S 0.0477(6) 0.0369(6) 0.0366(6) -0.0060(5) 0.0043(5) -0.0040(5) O2S 0.0522(8) 0.0769(9) 0.0456(7) -0.0224(6) -0.0078(6) -0.0127(7) O3S 0.0530(7) 0.0331(6) 0.0327(5) -0.0043(5) 0.0016(5) -0.0004(5) O4S 0.0563(7) 0.0433(7) 0.0474(7) -0.0062(5) -0.0070(6) -0.0051(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 O1 C4 1.3751(15) . ? O2 C5 1.3666(14) . ? O3 C6 1.3726(14) . ? O4 C9 1.3689(15) . ? O5 C15 1.3683(15) . ? C1 C14 1.5235(16) . ? C1 C2 1.5257(15) . ? C1 C8 1.5279(16) . ? C2 C3 1.3853(17) . ? C2 C7 1.3927(16) . ? C3 C4 1.3873(17) . ? C4 C5 1.3888(17) . ? C5 C6 1.3928(18) . ? C6 C7 1.3842(17) . ? C8 C13 1.3904(17) . ? C8 C9 1.3965(17) . ? C9 C10 1.3905(18) . ? C10 C11 1.3830(19) . ? C11 C12 1.376(2) . ? C12 C13 1.3938(18) . ? C14 C19 1.3861(17) . ? C14 C15 1.4012(17) . ? C15 C16 1.3871(19) . ? C16 C17 1.379(2) . ? C17 C18 1.379(2) . ? C18 C19 1.3917(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 C14 C1 C2 112.07(9) . . ? C14 C1 C8 112.76(9) . . ? C2 C1 C8 111.55(9) . . ? C3 C2 C7 119.27(10) . . ? C3 C2 C1 121.70(10) . . ? C7 C2 C1 118.91(10) . . ? C2 C3 C4 120.31(11) . . ? O1 C4 C3 122.33(11) . . ? O1 C4 C5 116.85(11) . . ? C3 C4 C5 120.81(11) . . ? O2 C5 C4 118.90(11) . . ? O2 C5 C6 122.49(11) . . ? C4 C5 C6 118.60(11) . . ? O3 C6 C7 122.45(11) . . ? O3 C6 C5 116.76(11) . . ? C7 C6 C5 120.79(11) . . ? C6 C7 C2 120.20(11) . . ? C13 C8 C9 117.68(11) . . ? C13 C8 C1 122.89(10) . . ? C9 C8 C1 119.43(10) . . ? O4 C9 C10 121.23(11) . . ? O4 C9 C8 117.78(11) . . ? C10 C9 C8 120.99(11) . . ? C11 C10 C9 119.90(12) . . ? C12 C11 C10 120.36(12) . . ? C11 C12 C13 119.37(12) . . ? C8 C13 C12 121.69(12) . . ? C19 C14 C15 117.76(11) . . ? C19 C14 C1 123.59(11) . . ? C15 C14 C1 118.64(10) . . ? O5 C15 C16 122.07(12) . . ? O5 C15 C14 116.93(11) . . ? C16 C15 C14 120.99(12) . . ? C17 C16 C15 119.92(13) . . ? C18 C17 C16 120.25(13) . . ? C17 C18 C19 119.63(13) . . ? C14 C19 C18 121.44(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 C14 C1 C2 C3 -34.66(15) . . . . ? C8 C1 C2 C3 92.85(13) . . . . ? C14 C1 C2 C7 149.32(11) . . . . ? C8 C1 C2 C7 -83.17(13) . . . . ? C7 C2 C3 C4 1.05(17) . . . . ? C1 C2 C3 C4 -174.97(10) . . . . ? C2 C3 C4 O1 178.46(11) . . . . ? C2 C3 C4 C5 -0.78(18) . . . . ? O1 C4 C5 O2 1.71(17) . . . . ? C3 C4 C5 O2 -179.01(11) . . . . ? O1 C4 C5 C6 -179.80(11) . . . . ? C3 C4 C5 C6 -0.53(18) . . . . ? O2 C5 C6 O3 0.20(18) . . . . ? C4 C5 C6 O3 -178.23(11) . . . . ? O2 C5 C6 C7 180.00(11) . . . . ? C4 C5 C6 C7 1.57(18) . . . . ? O3 C6 C7 C2 178.47(11) . . . . ? C5 C6 C7 C2 -1.31(18) . . . . ? C3 C2 C7 C6 -0.01(17) . . . . ? C1 C2 C7 C6 176.11(10) . . . . ? C14 C1 C8 C13 109.93(13) . . . . ? C2 C1 C8 C13 -17.20(16) . . . . ? C14 C1 C8 C9 -70.61(14) . . . . ? C2 C1 C8 C9 162.26(11) . . . . ? C13 C8 C9 O4 179.18(11) . . . . ? C1 C8 C9 O4 -0.30(17) . . . . ? C13 C8 C9 C10 -0.34(18) . . . . ? C1 C8 C9 C10 -179.83(11) . . . . ? O4 C9 C10 C11 -179.33(12) . . . . ? C8 C9 C10 C11 0.2(2) . . . . ? C9 C10 C11 C12 -0.1(2) . . . . ? C10 C11 C12 C13 0.2(2) . . . . ? C9 C8 C13 C12 0.43(19) . . . . ? C1 C8 C13 C12 179.90(11) . . . . ? C11 C12 C13 C8 -0.4(2) . . . . ? C2 C1 C14 C19 108.02(13) . . . . ? C8 C1 C14 C19 -18.84(16) . . . . ? C2 C1 C14 C15 -71.07(13) . . . . ? C8 C1 C14 C15 162.07(10) . . . . ? C19 C14 C15 O5 -178.85(11) . . . . ? C1 C14 C15 O5 0.29(16) . . . . ? C19 C14 C15 C16 0.36(18) . . . . ? C1 C14 C15 C16 179.51(11) . . . . ? O5 C15 C16 C17 178.93(13) . . . . ? C14 C15 C16 C17 -0.2(2) . . . . ? C15 C16 C17 C18 0.0(2) . . . . ? C16 C17 C18 C19 0.2(2) . . . . ? C15 C14 C19 C18 -0.21(19) . . . . ? C1 C14 C19 C18 -179.31(12) . . . . ? C17 C18 C19 C14 -0.1(2) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 30.01 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.340 _refine_diff_density_min -0.276 _refine_diff_density_rms 0.067 Hydrogen bonds with H..A < r(A) + 2.000 Angstroms and 110 deg. D-H d(D-H) d(H..A)