data_global _journal_name_full J.Mater.Chem. _journal_coden_Cambridge 1145 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_address ;Department of Organic Chemistry University of Madras, Chennai-25 India ; _publ_contact_author_name 'Thangamuthu Mohan Das' _publ_contact_author_email 'TMDAS 72@YAHOO.COM' _publ_section_title ; Design, synthesis, gelation studies of 4,6-O-butylidene-?-,?-unsaturated-?-C-glycosidic ketones: Application in tissue culture ; _publ_contact_author_address ;Department of Organic Chemistry University of Madras, Chennai-25 India ; _publ_contact_author_phone 9965048959 _publ_author_name 'Thangamuthu Mohan Das' # end Validation Reply Form # Attachment 'tmdn16.cif' data_tmdn16 _database_code_depnum_ccdc_archive 'CCDC 702166' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H28 N2 O6' _chemical_formula_weight 404.45 _chemical_absolute_configuration unk loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 4.8023(2) _cell_length_b 9.3324(3) _cell_length_c 12.6403(4) _cell_angle_alpha 70.868(2) _cell_angle_beta 80.910(2) _cell_angle_gamma 77.056(2) _cell_volume 519.41(3) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5356 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 27.6 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.293 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 216 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9767 _exptl_absorpt_correction_T_max 0.9813 _exptl_absorpt_process_details 'SADABS (Bruker 1999)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 axs kappa apex2 CCD Diffractometer' _diffrn_measurement_method '\w and \f scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 11660 _diffrn_reflns_av_R_equivalents 0.0207 _diffrn_reflns_av_sigmaI/netI 0.0264 _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 -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.71 _diffrn_reflns_theta_max 27.83 _reflns_number_total 4282 _reflns_number_gt 3717 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2004)' _computing_cell_refinement 'APEX2/SAINT (Bruker, 2004)' _computing_data_reduction 'SAINT/XPREP (Bruker, 2004)' _computing_structure_solution 'SIR92 (Altornare et al., 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0874P)^2^+0.0041P] 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 0.075(12) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.3(8) _refine_ls_number_reflns 4282 _refine_ls_number_parameters 338 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0526 _refine_ls_R_factor_gt 0.0430 _refine_ls_wR_factor_ref 0.1319 _refine_ls_wR_factor_gt 0.1160 _refine_ls_goodness_of_fit_ref 1.098 _refine_ls_restrained_S_all 1.097 _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 0.7204(4) -0.1161(2) 0.64385(15) 0.0302(4) Uani 1 1 d . . . C2 C 0.7435(4) 0.0546(2) 0.59860(15) 0.0307(4) Uani 1 1 d . . . C3 C 0.8302(4) 0.1044(2) 0.68982(16) 0.0328(4) Uani 1 1 d . . . C4 C 0.6276(4) 0.0625(2) 0.79393(15) 0.0315(4) Uani 1 1 d . . . C5 C 0.6241(4) -0.1085(2) 0.83034(16) 0.0321(4) Uani 1 1 d . . . C6 C 0.4306(5) -0.1497(3) 0.93770(17) 0.0430(5) Uani 1 1 d . . . C7 C 0.5329(4) 0.0595(2) 0.98155(17) 0.0382(4) Uani 1 1 d . . . C8 C 0.6413(5) 0.1002(3) 1.07118(18) 0.0448(5) Uani 1 1 d . . . C9 C 0.4475(7) 0.0781(4) 1.1789(2) 0.0608(7) Uani 1 1 d . . . C10 C 0.5457(8) 0.1302(4) 1.2643(2) 0.0701(8) Uani 1 1 d . . . H10A H 0.7304 0.0703 1.2848 0.105 Uiso 1 1 calc R . . H10B H 0.4105 0.1164 1.3298 0.105 Uiso 1 1 calc R . . H10C H 0.5594 0.2373 1.2332 0.105 Uiso 1 1 calc R . . C11 C 0.6093(4) -0.1676(2) 0.55923(18) 0.0346(4) Uani 1 1 d . . . C12 C 0.6279(4) -0.3394(2) 0.59205(16) 0.0353(4) Uani 1 1 d . . . C13 C 0.4725(4) -0.4026(3) 0.53109(18) 0.0404(5) Uani 1 1 d . . . C14 C 0.3310(4) -0.3250(2) 0.44290(18) 0.0371(4) Uani 1 1 d . . . C15 C 0.1848(4) -0.3927(2) 0.38311(17) 0.0370(4) Uani 1 1 d . . . C16 C 0.0813(6) -0.3084(3) 0.2804(2) 0.0531(6) Uani 1 1 d . . . C17 C -0.0576(6) -0.3757(3) 0.2271(2) 0.0627(7) Uani 1 1 d . . . C18 C -0.0914(6) -0.5254(3) 0.2785(2) 0.0524(6) Uani 1 1 d . . . C19 C 0.1358(4) -0.5434(2) 0.42787(19) 0.0400(5) Uani 1 1 d . . . N N 0.0010(4) -0.6100(2) 0.37782(17) 0.0461(4) Uani 1 1 d . . . O1 O 0.5247(3) -0.14413(15) 0.74349(11) 0.0348(3) Uani 1 1 d . . . O2 O 0.5316(3) -0.10016(16) 1.01797(11) 0.0438(4) Uani 1 1 d . . . O3 O 0.7187(3) 0.10043(15) 0.88177(11) 0.0369(3) Uani 1 1 d . . . O4 O 0.8220(5) 0.26542(19) 0.64583(16) 0.0617(5) Uani 1 1 d . . . O5 O 0.9493(3) 0.0723(2) 0.50436(13) 0.0396(3) Uani 1 1 d . . . O6 O 0.7716(3) -0.42721(18) 0.66625(14) 0.0493(4) Uani 1 1 d . . . C2A C 1.0394(7) -0.5176(4) 0.9366(3) 0.0740(8) Uiso 1 1 d . . . C1A C 1.2549(8) -0.5047(5) 0.8466(3) 0.0820(9) Uiso 1 1 d . . . H1A1 H 1.1842 -0.5159 0.7834 0.123 Uiso 1 1 calc R . . H1A2 H 1.4193 -0.5840 0.8688 0.123 Uiso 1 1 calc R . . H1A3 H 1.3085 -0.4053 0.8262 0.123 Uiso 1 1 calc R . . N1 N 0.8567(10) -0.5247(5) 1.0066(4) 0.1146(12) Uiso 1 1 d . . . H1 H 0.906(4) -0.173(2) 0.6629(17) 0.021(4) Uiso 1 1 d . . . H2 H 0.565(5) 0.112(3) 0.5807(18) 0.029(5) Uiso 1 1 d . . . H3 H 1.015(4) 0.049(2) 0.7041(17) 0.021(4) Uiso 1 1 d . . . H4 H 0.438(5) 0.113(3) 0.7827(19) 0.032(5) Uiso 1 1 d . . . H5 H 0.811(5) -0.162(3) 0.8452(19) 0.032(5) Uiso 1 1 d . . . H6A H 0.448(5) -0.267(4) 0.973(2) 0.048(6) Uiso 1 1 d . . . H6B H 0.236(6) -0.094(3) 0.924(2) 0.043(6) Uiso 1 1 d . . . H7 H 0.342(6) 0.108(3) 0.968(2) 0.039(6) Uiso 1 1 d . . . H9A H 0.273(8) 0.125(4) 1.175(3) 0.069(9) Uiso 1 1 d . . . H9B H 0.456(9) -0.041(5) 1.219(4) 0.091(11) Uiso 1 1 d . . . H11A H 0.729(5) -0.139(3) 0.490(2) 0.042(6) Uiso 1 1 d . . . H11B H 0.428(6) -0.116(3) 0.547(2) 0.047(6) Uiso 1 1 d . . . H14 H 0.325(6) -0.219(4) 0.411(2) 0.050(7) Uiso 1 1 d . . . H16 H 0.123(7) -0.212(4) 0.241(3) 0.067(9) Uiso 1 1 d . . . H17 H -0.137(9) -0.317(5) 0.154(3) 0.100(12) Uiso 1 1 d . . . H18 H -0.195(7) -0.560(4) 0.246(3) 0.067(8) Uiso 1 1 d . . . H19 H 0.189(6) -0.600(3) 0.503(3) 0.055(7) Uiso 1 1 d . . . H13 H 0.481(6) -0.512(3) 0.562(2) 0.049(6) Uiso 1 1 d . . . H5' H 0.960(6) 0.159(4) 0.474(3) 0.056(8) Uiso 1 1 d . . . H4' H 0.837(6) 0.299(4) 0.691(3) 0.055(8) Uiso 1 1 d . . . H8A H 0.807(5) 0.040(3) 1.0907(17) 0.024(5) Uiso 1 1 d . . . H8B H 0.638(7) 0.210(4) 1.038(3) 0.065(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 C1 0.0347(8) 0.0274(9) 0.0308(9) -0.0111(7) -0.0050(7) -0.0057(7) C2 0.0367(8) 0.0266(9) 0.0293(9) -0.0094(7) -0.0056(7) -0.0036(7) C3 0.0441(9) 0.0248(9) 0.0318(10) -0.0088(8) -0.0052(8) -0.0096(7) C4 0.0377(8) 0.0295(10) 0.0296(9) -0.0103(7) -0.0076(7) -0.0056(7) C5 0.0408(9) 0.0267(9) 0.0304(9) -0.0072(7) -0.0070(7) -0.0089(7) C6 0.0579(13) 0.0441(13) 0.0356(11) -0.0140(10) -0.0032(9) -0.0244(10) C7 0.0458(11) 0.0400(11) 0.0326(10) -0.0120(9) -0.0023(8) -0.0146(9) C8 0.0577(13) 0.0498(14) 0.0349(11) -0.0158(10) -0.0029(9) -0.0224(11) C9 0.0712(17) 0.082(2) 0.0424(13) -0.0283(14) 0.0076(12) -0.0350(15) C10 0.0908(19) 0.089(2) 0.0441(14) -0.0346(15) 0.0030(13) -0.0293(17) C11 0.0411(9) 0.0323(10) 0.0352(10) -0.0133(8) -0.0074(8) -0.0092(8) C12 0.0420(9) 0.0324(10) 0.0352(10) -0.0148(8) -0.0041(8) -0.0073(8) C13 0.0507(9) 0.0315(11) 0.0445(12) -0.0145(9) -0.0112(9) -0.0095(8) C14 0.0448(9) 0.0318(11) 0.0371(10) -0.0092(8) -0.0036(8) -0.0138(8) C15 0.0408(9) 0.0368(11) 0.0367(10) -0.0115(9) -0.0049(7) -0.0123(8) C16 0.0726(14) 0.0423(14) 0.0480(13) -0.0012(11) -0.0201(11) -0.0266(11) C17 0.0856(17) 0.0598(17) 0.0471(14) 0.0003(12) -0.0316(13) -0.0298(14) C18 0.0695(14) 0.0563(15) 0.0453(13) -0.0204(11) -0.0109(11) -0.0282(11) C19 0.0473(10) 0.0353(11) 0.0376(11) -0.0078(9) -0.0046(8) -0.0125(8) N 0.0582(10) 0.0404(10) 0.0465(11) -0.0162(8) -0.0030(8) -0.0193(8) O1 0.0410(6) 0.0366(8) 0.0334(7) -0.0139(6) -0.0046(5) -0.0146(5) O2 0.0664(9) 0.0408(9) 0.0291(7) -0.0070(6) -0.0071(6) -0.0231(7) O3 0.0488(7) 0.0377(8) 0.0304(7) -0.0133(6) -0.0028(6) -0.0165(6) O4 0.1209(16) 0.0330(9) 0.0385(9) -0.0129(7) 0.0048(9) -0.0343(9) O5 0.0560(8) 0.0311(8) 0.0315(7) -0.0093(6) 0.0029(6) -0.0129(6) O6 0.0661(9) 0.0344(8) 0.0520(9) -0.0141(7) -0.0261(8) -0.0029(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.435(2) . ? C1 C11 1.514(2) . ? C1 C2 1.529(2) . ? C1 H1 0.95(2) . ? C2 O5 1.412(2) . ? C2 C3 1.519(2) . ? C2 H2 0.92(2) . ? C3 O4 1.415(3) . ? C3 C4 1.503(3) . ? C3 H3 0.93(2) . ? C4 O3 1.425(2) . ? C4 C5 1.513(3) . ? C4 H4 0.94(2) . ? C5 O1 1.421(2) . ? C5 C6 1.507(3) . ? C5 H5 0.94(2) . ? C6 O2 1.429(2) . ? C6 H6A 1.03(3) . ? C6 H6B 0.97(3) . ? C7 O2 1.409(3) . ? C7 O3 1.419(2) . ? C7 C8 1.502(3) . ? C7 H7 0.94(3) . ? C8 C9 1.505(4) . ? C8 H8A 0.88(2) . ? C8 H8B 0.97(4) . ? C9 C10 1.494(4) . ? C9 H9A 0.86(4) . ? C9 H9B 1.05(5) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C12 1.504(3) . ? C11 H11A 0.96(3) . ? C11 H11B 0.90(3) . ? C12 O6 1.215(2) . ? C12 C13 1.475(2) . ? C13 C14 1.311(3) . ? C13 H13 0.96(3) . ? C14 C15 1.464(2) . ? C14 H14 0.93(3) . ? C15 C16 1.383(3) . ? C15 C19 1.392(3) . ? C16 C17 1.378(3) . ? C16 H16 0.92(4) . ? C17 C18 1.369(4) . ? C17 H17 0.99(4) . ? C18 N 1.329(3) . ? C18 H18 0.86(3) . ? C19 N 1.331(3) . ? C19 H19 0.97(3) . ? O4 H4' 0.76(3) . ? O5 H5' 0.79(4) . ? C2A N1 1.139(5) . ? C2A C1A 1.406(5) . ? C1A H1A1 0.9600 . ? C1A H1A2 0.9600 . ? C1A H1A3 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 O1 C1 C11 107.16(14) . . ? O1 C1 C2 110.55(13) . . ? C11 C1 C2 111.65(14) . . ? O1 C1 H1 108.5(12) . . ? C11 C1 H1 111.6(12) . . ? C2 C1 H1 107.3(12) . . ? O5 C2 C3 111.43(15) . . ? O5 C2 C1 107.48(14) . . ? C3 C2 C1 109.74(14) . . ? O5 C2 H2 112.5(14) . . ? C3 C2 H2 107.0(14) . . ? C1 C2 H2 108.7(14) . . ? O4 C3 C4 112.35(17) . . ? O4 C3 C2 106.68(16) . . ? C4 C3 C2 109.31(14) . . ? O4 C3 H3 112.3(13) . . ? C4 C3 H3 109.9(12) . . ? C2 C3 H3 106.0(12) . . ? O3 C4 C3 109.44(14) . . ? O3 C4 C5 109.45(14) . . ? C3 C4 C5 109.89(14) . . ? O3 C4 H4 108.6(14) . . ? C3 C4 H4 112.8(14) . . ? C5 C4 H4 106.6(14) . . ? O1 C5 C6 110.76(14) . . ? O1 C5 C4 108.93(13) . . ? C6 C5 C4 109.13(15) . . ? O1 C5 H5 111.6(14) . . ? C6 C5 H5 108.1(14) . . ? C4 C5 H5 108.2(14) . . ? O2 C6 C5 107.40(15) . . ? O2 C6 H6A 104.7(15) . . ? C5 C6 H6A 111.9(14) . . ? O2 C6 H6B 108.2(15) . . ? C5 C6 H6B 109.5(15) . . ? H6A C6 H6B 115(2) . . ? O2 C7 O3 110.93(16) . . ? O2 C7 C8 108.78(17) . . ? O3 C7 C8 107.97(16) . . ? O2 C7 H7 105.8(16) . . ? O3 C7 H7 110.3(16) . . ? C8 C7 H7 113.0(15) . . ? C7 C8 C9 113.88(19) . . ? C7 C8 H8A 110.6(14) . . ? C9 C8 H8A 104.8(13) . . ? C7 C8 H8B 102.5(18) . . ? C9 C8 H8B 107.4(19) . . ? H8A C8 H8B 118(2) . . ? C10 C9 C8 113.5(2) . . ? C10 C9 H9A 103(2) . . ? C8 C9 H9A 117(2) . . ? C10 C9 H9B 103(2) . . ? C8 C9 H9B 109(2) . . ? H9A C9 H9B 110(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 . . ? C12 C11 C1 113.50(16) . . ? C12 C11 H11A 106.9(15) . . ? C1 C11 H11A 107.2(15) . . ? C12 C11 H11B 111.7(17) . . ? C1 C11 H11B 109.0(16) . . ? H11A C11 H11B 108(2) . . ? O6 C12 C13 119.32(17) . . ? O6 C12 C11 121.51(16) . . ? C13 C12 C11 119.16(16) . . ? C14 C13 C12 126.64(18) . . ? C14 C13 H13 119.7(16) . . ? C12 C13 H13 113.7(16) . . ? C13 C14 C15 124.99(19) . . ? C13 C14 H14 120.6(16) . . ? C15 C14 H14 114.4(16) . . ? C16 C15 C19 116.60(17) . . ? C16 C15 C14 121.47(19) . . ? C19 C15 C14 121.91(17) . . ? C17 C16 C15 119.8(2) . . ? C17 C16 H16 117.6(19) . . ? C15 C16 H16 122.1(19) . . ? C18 C17 C16 118.6(2) . . ? C18 C17 H17 120(2) . . ? C16 C17 H17 121(2) . . ? N C18 C17 123.6(2) . . ? N C18 H18 120(2) . . ? C17 C18 H18 116(2) . . ? N C19 C15 124.38(19) . . ? N C19 H19 118.0(17) . . ? C15 C19 H19 117.4(17) . . ? C18 N C19 117.0(2) . . ? C5 O1 C1 110.79(13) . . ? C7 O2 C6 112.74(15) . . ? C7 O3 C4 110.40(14) . . ? C3 O4 H4' 111(2) . . ? C2 O5 H5' 112(2) . . ? N1 C2A C1A 177.2(4) . . ? C2A C1A H1A1 109.5 . . ? C2A C1A H1A2 109.5 . . ? H1A1 C1A H1A2 109.5 . . ? C2A C1A H1A3 109.5 . . ? H1A1 C1A H1A3 109.5 . . ? H1A2 C1A H1A3 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 O1 C1 C2 O5 177.13(14) . . . . ? C11 C1 C2 O5 -63.68(17) . . . . ? O1 C1 C2 C3 55.80(17) . . . . ? C11 C1 C2 C3 174.99(16) . . . . ? O5 C2 C3 O4 66.3(2) . . . . ? C1 C2 C3 O4 -174.81(16) . . . . ? O5 C2 C3 C4 -172.03(15) . . . . ? C1 C2 C3 C4 -53.11(17) . . . . ? O4 C3 C4 O3 -65.3(2) . . . . ? C2 C3 C4 O3 176.44(14) . . . . ? O4 C3 C4 C5 174.45(16) . . . . ? C2 C3 C4 C5 56.23(17) . . . . ? O3 C4 C5 O1 178.24(15) . . . . ? C3 C4 C5 O1 -61.55(17) . . . . ? O3 C4 C5 C6 57.21(17) . . . . ? C3 C4 C5 C6 177.42(15) . . . . ? O1 C5 C6 O2 -175.74(15) . . . . ? C4 C5 C6 O2 -55.8(2) . . . . ? O2 C7 C8 C9 -65.5(3) . . . . ? O3 C7 C8 C9 174.1(2) . . . . ? C7 C8 C9 C10 -175.6(3) . . . . ? O1 C1 C11 C12 -68.2(2) . . . . ? C2 C1 C11 C12 170.65(15) . . . . ? C1 C11 C12 O6 -14.3(3) . . . . ? C1 C11 C12 C13 166.98(17) . . . . ? O6 C12 C13 C14 -173.3(2) . . . . ? C11 C12 C13 C14 5.5(3) . . . . ? C12 C13 C14 C15 178.53(18) . . . . ? C13 C14 C15 C16 -169.1(2) . . . . ? C13 C14 C15 C19 12.7(3) . . . . ? C19 C15 C16 C17 -1.1(4) . . . . ? C14 C15 C16 C17 -179.4(2) . . . . ? C15 C16 C17 C18 0.5(4) . . . . ? C16 C17 C18 N 0.4(5) . . . . ? C16 C15 C19 N 0.8(3) . . . . ? C14 C15 C19 N 179.1(2) . . . . ? C17 C18 N C19 -0.7(4) . . . . ? C15 C19 N C18 0.1(3) . . . . ? C6 C5 O1 C1 -175.60(15) . . . . ? C4 C5 O1 C1 64.37(17) . . . . ? C11 C1 O1 C5 176.02(14) . . . . ? C2 C1 O1 C5 -62.10(17) . . . . ? O3 C7 O2 C6 -61.5(2) . . . . ? C8 C7 O2 C6 179.92(18) . . . . ? C5 C6 O2 C7 58.8(2) . . . . ? O2 C7 O3 C4 60.20(18) . . . . ? C8 C7 O3 C4 179.31(17) . . . . ? C3 C4 O3 C7 -179.05(15) . . . . ? C5 C4 O3 C7 -58.57(18) . . . . ? 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 O5 H5' N 0.79(4) 2.13(4) 2.917(3) 175(3) 1_665 O4 H4' O6 0.76(3) 2.42(3) 2.917(2) 124(3) 1_565 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.83 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.332 _refine_diff_density_min -0.244 _refine_diff_density_rms 0.089 # Attachment 'sn15.cif' data_sn15 _database_code_depnum_ccdc_archive 'CCDC 702168' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H26 O7' _chemical_formula_sum 'C20 H26 O7' _chemical_formula_weight 378.41 _chemical_absolute_configuration unk 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 P21 _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 4.9409(7) _cell_length_b 33.746(5) _cell_length_c 5.7154(9) _cell_angle_alpha 90.00 _cell_angle_beta 101.967(9) _cell_angle_gamma 90.00 _cell_volume 932.2(2) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4664 _cell_measurement_theta_min 3.64 _cell_measurement_theta_max 28.13 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.348 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 404 _exptl_absorpt_coefficient_mu 0.102 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9822 _exptl_absorpt_correction_T_max 0.9895 _exptl_absorpt_process_details 'SADABS (Bruker, 1999)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 axs kappa apex2 CCD diffractometer' _diffrn_measurement_method '\w and \f scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 9350 _diffrn_reflns_av_R_equivalents 0.0286 _diffrn_reflns_av_sigmaI/netI 0.0234 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -44 _diffrn_reflns_limit_k_max 43 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 3.64 _diffrn_reflns_theta_max 28.13 _reflns_number_total 2268 _reflns_number_gt 2048 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2004)' _computing_cell_refinement 'APEX2/SAINT (Bruker, 2004)' _computing_data_reduction 'SAINT/XPREP (Bruker, 2004)' _computing_structure_solution 'SIR92 (Altornare et al., 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0531P)^2^+0.1150P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.100(1) _refine_ls_number_reflns 2268 _refine_ls_number_parameters 283 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0437 _refine_ls_R_factor_gt 0.0376 _refine_ls_wR_factor_ref 0.0997 _refine_ls_wR_factor_gt 0.0962 _refine_ls_goodness_of_fit_ref 1.080 _refine_ls_restrained_S_all 1.079 _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 0.4169(5) 0.05133(7) 1.0295(4) 0.0356(5) Uani 1 1 d . . . C2 C 0.2539(5) 0.05409(7) 1.2022(4) 0.0367(5) Uani 1 1 d . . . C3 C 0.2207(6) 0.02185(8) 1.3428(5) 0.0468(6) Uani 1 1 d . . . H3 H 0.1111 0.0239 1.4563 0.056 Uiso 1 1 calc R . . C4 C 0.3497(7) -0.01317(9) 1.3141(6) 0.0567(8) Uani 1 1 d . . . H4 H 0.3280 -0.0348 1.4092 0.068 Uiso 1 1 calc R . . C5 C 0.5114(8) -0.01661(8) 1.1456(7) 0.0581(8) Uani 1 1 d . . . H5 H 0.5990 -0.0405 1.1279 0.070 Uiso 1 1 calc R . . C6 C 0.5436(6) 0.01513(8) 1.0037(6) 0.0472(6) Uani 1 1 d . . . H6 H 0.6511 0.0125 0.8890 0.057 Uiso 1 1 calc R . . C7 C 0.4466(5) 0.08620(7) 0.8851(4) 0.0343(5) Uani 1 1 d . . . C8 C 0.6129(5) 0.08968(7) 0.7326(5) 0.0354(5) Uani 1 1 d . . . C9 C 0.6376(4) 0.12451(7) 0.5885(4) 0.0322(4) Uani 1 1 d . . . C10 C 0.4681(5) 0.16139(6) 0.6002(5) 0.0324(5) Uani 1 1 d . . . H10A H 0.3463 0.1570 0.7108 0.039 Uiso 1 1 calc R . . H10B H 0.3539 0.1665 0.4435 0.039 Uiso 1 1 calc R . . C11 C 0.6484(4) 0.19725(6) 0.6803(4) 0.0281(4) Uani 1 1 d . . . C12 C 0.7696(4) 0.19733(6) 0.9493(4) 0.0301(4) Uani 1 1 d . . . C13 C 0.9195(4) 0.23558(6) 1.0330(4) 0.0294(4) Uani 1 1 d . . . C14 C 0.7318(4) 0.26990(6) 0.9423(4) 0.0304(4) Uani 1 1 d . . . C15 C 0.6263(5) 0.26691(7) 0.6751(4) 0.0326(5) Uani 1 1 d . . . C16 C 0.4401(6) 0.30194(8) 0.5929(5) 0.0472(6) Uani 1 1 d . . . H16A H 0.3784 0.3015 0.4203 0.057 Uiso 1 1 calc R . . H16B H 0.2788 0.3011 0.6647 0.057 Uiso 1 1 calc R . . C17 C 0.6986(6) 0.33840(7) 0.9142(5) 0.0434(6) Uani 1 1 d . . . C18 C 0.8612(7) 0.37595(8) 0.9741(6) 0.0545(8) Uani 1 1 d . . . H18A H 0.7493 0.3981 0.9024 0.065 Uiso 1 1 calc R . . H18B H 1.0241 0.3749 0.9044 0.065 Uiso 1 1 calc R . . C19 C 0.9503(9) 0.38305(11) 1.2390(8) 0.0713(10) Uani 1 1 d . . . H19A H 0.7874 0.3834 1.3089 0.086 Uiso 1 1 calc R . . H19B H 1.0654 0.3611 1.3097 0.086 Uiso 1 1 calc R . . C20 C 1.1070(11) 0.42089(14) 1.3019(9) 0.0923(14) Uani 1 1 d . . . H20A H 1.2637 0.4214 1.2268 0.138 Uiso 1 1 calc R . . H20B H 1.1695 0.4225 1.4723 0.138 Uiso 1 1 calc R . . H20C H 0.9884 0.4430 1.2470 0.138 Uiso 1 1 calc R . . O1 O 0.1389(4) 0.08945(6) 1.2252(4) 0.0479(5) Uani 1 1 d . . . H1 H 0.0516 0.0884 1.3323 0.072 Uiso 1 1 calc R . . O2 O 0.7960(4) 0.12384(6) 0.4488(4) 0.0458(4) Uani 1 1 d . . . O3 O 0.9617(4) 0.16535(5) 0.9970(4) 0.0478(5) Uani 1 1 d . . . O4 O 0.9825(4) 0.23654(6) 1.2863(3) 0.0462(4) Uani 1 1 d . . . O5 O 0.4734(3) 0.23117(4) 0.6197(3) 0.0339(4) Uani 1 1 d . . . O6 O 0.5966(5) 0.33696(5) 0.6651(4) 0.0526(5) Uani 1 1 d . . . O7 O 0.8776(3) 0.30626(5) 0.9930(3) 0.0383(4) Uani 1 1 d . . . H11 H 0.796(5) 0.1986(8) 0.591(5) 0.030(6) Uiso 1 1 d . . . H17 H 0.537(6) 0.3349(8) 0.988(5) 0.028(6) Uiso 1 1 d . . . H14 H 0.570(5) 0.2684(8) 1.023(5) 0.031(6) Uiso 1 1 d . . . H15 H 0.788(6) 0.2662(9) 0.595(5) 0.037(7) Uiso 1 1 d . . . H12 H 0.618(5) 0.1949(8) 1.041(5) 0.034(7) Uiso 1 1 d . . . H13 H 1.094(6) 0.2369(9) 0.967(5) 0.042(7) Uiso 1 1 d . . . H7 H 0.336(6) 0.1082(9) 0.910(5) 0.036(7) Uiso 1 1 d . . . H8 H 0.731(7) 0.0673(10) 0.712(6) 0.048(8) Uiso 1 1 d . . . H3A H 0.928(9) 0.1551(13) 1.105(8) 0.072 Uiso 1 1 d . . . H4A H 1.133(9) 0.2337(13) 1.335(8) 0.072 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 C1 0.0391(12) 0.0327(11) 0.0346(12) 0.0013(9) 0.0067(9) -0.0031(9) C2 0.0387(12) 0.0372(12) 0.0332(12) 0.0018(9) 0.0051(9) -0.0033(9) C3 0.0541(15) 0.0481(15) 0.0400(14) 0.0068(11) 0.0141(12) -0.0082(12) C4 0.076(2) 0.0367(14) 0.0584(19) 0.0140(13) 0.0154(16) -0.0053(13) C5 0.074(2) 0.0330(14) 0.070(2) 0.0054(13) 0.0212(16) 0.0068(12) C6 0.0584(16) 0.0347(13) 0.0522(16) 0.0016(11) 0.0203(13) 0.0023(11) C7 0.0387(11) 0.0296(11) 0.0345(11) -0.0010(9) 0.0073(9) 0.0013(9) C8 0.0399(11) 0.0276(11) 0.0406(12) -0.0017(9) 0.0124(9) 0.0021(9) C9 0.0325(10) 0.0283(10) 0.0359(12) -0.0042(9) 0.0075(8) -0.0020(8) C10 0.0316(11) 0.0273(10) 0.0371(12) 0.0007(8) 0.0045(9) -0.0020(8) C11 0.0285(9) 0.0237(9) 0.0317(11) 0.0026(8) 0.0055(8) 0.0015(8) C12 0.0308(9) 0.0279(10) 0.0304(11) 0.0056(8) 0.0033(8) 0.0007(8) C13 0.0290(9) 0.0306(10) 0.0274(10) 0.0016(9) 0.0029(8) 0.0006(8) C14 0.0300(10) 0.0263(10) 0.0345(12) -0.0014(9) 0.0059(8) 0.0001(8) C15 0.0374(11) 0.0265(10) 0.0324(11) 0.0027(9) 0.0034(9) 0.0007(9) C16 0.0576(15) 0.0318(12) 0.0441(15) 0.0037(10) -0.0079(11) 0.0063(11) C17 0.0501(14) 0.0303(12) 0.0486(15) -0.0020(10) 0.0077(11) 0.0033(10) C18 0.0671(18) 0.0296(13) 0.065(2) -0.0024(12) 0.0093(15) -0.0038(12) C19 0.091(3) 0.0510(19) 0.068(2) -0.0085(16) 0.0064(19) -0.0146(17) C20 0.107(3) 0.071(3) 0.094(3) -0.029(2) 0.008(3) -0.028(2) O1 0.0583(11) 0.0425(10) 0.0491(11) 0.0085(8) 0.0255(9) 0.0097(8) O2 0.0521(10) 0.0384(9) 0.0546(12) 0.0010(8) 0.0285(9) 0.0011(8) O3 0.0533(11) 0.0321(9) 0.0513(11) 0.0082(8) -0.0044(9) 0.0099(8) O4 0.0439(9) 0.0583(11) 0.0318(9) -0.0016(8) -0.0031(7) 0.0046(9) O5 0.0348(7) 0.0268(8) 0.0355(8) 0.0017(6) -0.0036(6) 0.0030(6) O6 0.0714(13) 0.0280(9) 0.0521(11) 0.0048(8) -0.0014(9) -0.0009(8) O7 0.0385(8) 0.0271(8) 0.0464(10) -0.0043(7) 0.0022(7) -0.0018(7) _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 C6 1.394(4) . ? C1 C2 1.401(3) . ? C1 C7 1.462(3) . ? C2 O1 1.340(3) . ? C2 C3 1.382(4) . ? C3 C4 1.368(4) . ? C3 H3 0.9300 . ? C4 C5 1.378(5) . ? C4 H4 0.9300 . ? C5 C6 1.372(4) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C8 1.321(3) . ? C7 H7 0.95(3) . ? C8 C9 1.455(3) . ? C8 H8 0.98(3) . ? C9 O2 1.229(3) . ? C9 C10 1.509(3) . ? C10 C11 1.516(3) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 O5 1.433(2) . ? C11 C12 1.530(3) . ? C11 H11 0.97(3) . ? C12 O3 1.426(3) . ? C12 C13 1.515(3) . ? C12 H12 1.00(3) . ? C13 O4 1.417(3) . ? C13 C14 1.507(3) . ? C13 H13 1.01(3) . ? C14 O7 1.422(3) . ? C14 C15 1.512(3) . ? C14 H14 1.00(3) . ? C15 O5 1.424(3) . ? C15 C16 1.512(3) . ? C15 H15 1.00(3) . ? C16 O6 1.426(3) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 O6 1.409(4) . ? C17 O7 1.413(3) . ? C17 C18 1.501(4) . ? C17 H17 0.98(3) . ? C18 C19 1.505(5) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 C20 1.498(5) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? O1 H1 0.8200 . ? O3 H3A 0.76(4) . ? O4 H4A 0.75(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 C6 C1 C2 118.0(2) . . ? C6 C1 C7 123.1(2) . . ? C2 C1 C7 119.0(2) . . ? O1 C2 C3 122.7(2) . . ? O1 C2 C1 116.5(2) . . ? C3 C2 C1 120.8(2) . . ? C4 C3 C2 119.7(3) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C3 C4 C5 120.6(3) . . ? C3 C4 H4 119.7 . . ? C5 C4 H4 119.7 . . ? C6 C5 C4 120.1(3) . . ? C6 C5 H5 119.9 . . ? C4 C5 H5 119.9 . . ? C5 C6 C1 120.8(3) . . ? C5 C6 H6 119.6 . . ? C1 C6 H6 119.6 . . ? C8 C7 C1 126.4(2) . . ? C8 C7 H7 119.1(17) . . ? C1 C7 H7 114.6(17) . . ? C7 C8 C9 125.6(2) . . ? C7 C8 H8 119(2) . . ? C9 C8 H8 116(2) . . ? O2 C9 C8 119.5(2) . . ? O2 C9 C10 118.5(2) . . ? C8 C9 C10 121.9(2) . . ? C9 C10 C11 112.03(18) . . ? C9 C10 H10A 109.2 . . ? C11 C10 H10A 109.2 . . ? C9 C10 H10B 109.2 . . ? C11 C10 H10B 109.2 . . ? H10A C10 H10B 107.9 . . ? O5 C11 C10 106.11(16) . . ? O5 C11 C12 109.40(17) . . ? C10 C11 C12 112.83(18) . . ? O5 C11 H11 108.4(16) . . ? C10 C11 H11 109.7(16) . . ? C12 C11 H11 110.3(16) . . ? O3 C12 C13 108.78(17) . . ? O3 C12 C11 107.27(18) . . ? C13 C12 C11 112.49(17) . . ? O3 C12 H12 112.2(16) . . ? C13 C12 H12 105.9(16) . . ? C11 C12 H12 110.3(15) . . ? O4 C13 C14 108.83(18) . . ? O4 C13 C12 109.35(19) . . ? C14 C13 C12 108.69(16) . . ? O4 C13 H13 110.9(17) . . ? C14 C13 H13 110.4(17) . . ? C12 C13 H13 108.6(18) . . ? O7 C14 C13 110.09(17) . . ? O7 C14 C15 108.50(18) . . ? C13 C14 C15 110.79(18) . . ? O7 C14 H14 111.7(16) . . ? C13 C14 H14 107.3(16) . . ? C15 C14 H14 108.5(15) . . ? O5 C15 C16 109.44(18) . . ? O5 C15 C14 109.71(18) . . ? C16 C15 C14 108.79(19) . . ? O5 C15 H15 108.3(17) . . ? C16 C15 H15 111.6(17) . . ? C14 C15 H15 109.0(16) . . ? O6 C16 C15 107.4(2) . . ? O6 C16 H16A 110.2 . . ? C15 C16 H16A 110.2 . . ? O6 C16 H16B 110.2 . . ? C15 C16 H16B 110.2 . . ? H16A C16 H16B 108.5 . . ? O6 C17 O7 111.4(2) . . ? O6 C17 C18 108.8(2) . . ? O7 C17 C18 107.8(2) . . ? O6 C17 H17 106.2(16) . . ? O7 C17 H17 106.2(16) . . ? C18 C17 H17 116.5(16) . . ? C17 C18 C19 113.2(3) . . ? C17 C18 H18A 108.9 . . ? C19 C18 H18A 108.9 . . ? C17 C18 H18B 108.9 . . ? C19 C18 H18B 108.9 . . ? H18A C18 H18B 107.7 . . ? C20 C19 C18 113.9(3) . . ? C20 C19 H19A 108.8 . . ? C18 C19 H19A 108.8 . . ? C20 C19 H19B 108.8 . . ? C18 C19 H19B 108.8 . . ? H19A C19 H19B 107.7 . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C2 O1 H1 109.5 . . ? C12 O3 H3A 104(3) . . ? C13 O4 H4A 112(3) . . ? C15 O5 C11 110.94(15) . . ? C17 O6 C16 112.4(2) . . ? C17 O7 C14 109.90(18) . . ? 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 C6 C1 C2 O1 178.9(2) . . . . ? C7 C1 C2 O1 -1.1(3) . . . . ? C6 C1 C2 C3 0.1(4) . . . . ? C7 C1 C2 C3 -179.9(2) . . . . ? O1 C2 C3 C4 -178.3(3) . . . . ? C1 C2 C3 C4 0.4(4) . . . . ? C2 C3 C4 C5 -0.3(5) . . . . ? C3 C4 C5 C6 -0.3(5) . . . . ? C4 C5 C6 C1 0.8(5) . . . . ? C2 C1 C6 C5 -0.7(4) . . . . ? C7 C1 C6 C5 179.3(3) . . . . ? C6 C1 C7 C8 -7.2(4) . . . . ? C2 C1 C7 C8 172.9(2) . . . . ? C1 C7 C8 C9 179.3(2) . . . . ? C7 C8 C9 O2 -178.4(2) . . . . ? C7 C8 C9 C10 -0.1(4) . . . . ? O2 C9 C10 C11 -62.0(3) . . . . ? C8 C9 C10 C11 119.6(2) . . . . ? C9 C10 C11 O5 164.08(19) . . . . ? C9 C10 C11 C12 -76.1(2) . . . . ? O5 C11 C12 O3 -174.55(18) . . . . ? C10 C11 C12 O3 67.6(2) . . . . ? O5 C11 C12 C13 -55.0(2) . . . . ? C10 C11 C12 C13 -172.84(18) . . . . ? O3 C12 C13 O4 -71.7(2) . . . . ? C11 C12 C13 O4 169.63(18) . . . . ? O3 C12 C13 C14 169.64(19) . . . . ? C11 C12 C13 C14 50.9(2) . . . . ? O4 C13 C14 O7 68.0(2) . . . . ? C12 C13 C14 O7 -173.02(18) . . . . ? O4 C13 C14 C15 -172.00(18) . . . . ? C12 C13 C14 C15 -53.0(2) . . . . ? O7 C14 C15 O5 -178.59(17) . . . . ? C13 C14 C15 O5 60.5(2) . . . . ? O7 C14 C15 C16 -58.9(2) . . . . ? C13 C14 C15 C16 -179.9(2) . . . . ? O5 C15 C16 O6 176.4(2) . . . . ? C14 C15 C16 O6 56.6(3) . . . . ? O6 C17 C18 C19 172.8(3) . . . . ? O7 C17 C18 C19 -66.3(4) . . . . ? C17 C18 C19 C20 -178.6(3) . . . . ? C16 C15 O5 C11 176.0(2) . . . . ? C14 C15 O5 C11 -64.7(2) . . . . ? C10 C11 O5 C15 -176.69(19) . . . . ? C12 C11 O5 C15 61.3(2) . . . . ? O7 C17 O6 C16 61.1(3) . . . . ? C18 C17 O6 C16 179.7(2) . . . . ? C15 C16 O6 C17 -58.0(3) . . . . ? O6 C17 O7 C14 -61.4(3) . . . . ? C18 C17 O7 C14 179.4(2) . . . . ? C13 C14 O7 C17 -178.2(2) . . . . ? C15 C14 O7 C17 60.4(2) . . . . ? 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 H1 O2 0.82 1.95 2.598(2) 134.8 1_456 O3 H3A O2 0.76(4) 2.44(4) 3.190(3) 177(5) 1_556 O3 H3A O1 0.76(4) 2.49(4) 2.925(3) 119(4) 1_655 O4 H4A O5 0.75(4) 2.08(4) 2.762(2) 151(4) 1_656 _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.206 _refine_diff_density_min -0.158 _refine_diff_density_rms 0.040 _vrf_PLAT220_sn15 ; PROBLEM: Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.93 Ratio RESPONSE: This is due to the large libration amplitude of terminal carbon atom and the associated hydrogens as compared to the very small libration amplitudes of atoms close to libration axis. ; _vrf_PLAT222_sn15 ; PROBLEM:Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.29 Ratio RESPONSE: This is due to the large libration amplitude of terminal carbon atom and the associated hydrogens as compared to the very small libration amplitudes of atoms close to libration axis. ;