# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2003 data_global _publ_contact_author 'G. Mehta' _publ_contact_author_email gm@orgchem.iisc.ernet.in loop_ _publ_author_name 'Mehta, Goverdhan' 'Kotapalli, Pallavi' _journal_coden_Cambridge 182 _journal_name_full 'chemical communication' _journal_volume ? _journal_page_first ? _journal_page_last ? _journal_year ? _publ_contact_author_name 'Prof Goverdhan Mehta' _publ_contact_author_address ; Prof Goverdhan Mehta Organic Chemistry Indian Institute of Science Malleswaram Bangalore 560012 INDIA ; _publ_contact_author_email 'GM@ORGCHEM.IISC.ERNET.IN' _publ_section_title ; From hydrocarbons to polyols. Cyclooctatetraene to novel cyclooctitols ; data_kp1_m _database_code_CSD 193886 _audit_creation_date 2002-09-11T21:53:12-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; (3aR*,4R*,9R*,9aS*)-9-(hydroxymethyl)-2,2-dimethyl-3a,4,7,8,9,9a- hexahydrocycloocta[d][1,3]dioxol-4-ol ; _chemical_formula_sum 'C12 H20 O4' _chemical_formula_weight 228.28 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P2(1)/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.897(2) _cell_length_b 14.341(4) _cell_length_c 19.653(5) _cell_angle_alpha 90 _cell_angle_beta 102.263(6) _cell_angle_gamma 90 _cell_volume 2450.2(11) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_density_diffrn 1.238 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 992 _exptl_special_details ? _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max .230 _exptl_crystal_size_mid ? _exptl_crystal_size_min .07 #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_reflns_av_unetI/netI 0.1199 _diffrn_reflns_number 12483 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 26.85 _diffrn_reflns_theta_full 26.85 _diffrn_measured_fraction_theta_full 0.897 _diffrn_measured_fraction_theta_max 0.897 _reflns_number_total 4718 _reflns_number_gt 2482 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.1000P)^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_number_reflns 4718 _refine_ls_number_parameters 449 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.184 _refine_ls_R_factor_gt 0.0946 _refine_ls_wR_factor_ref 0.2193 _refine_ls_wR_factor_gt 0.1809 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _refine_ls_shift/su_max 0.016 _refine_ls_shift/su_mean 0.002 _refine_diff_density_max 0.261 _refine_diff_density_min -0.236 _refine_diff_density_rms 0.056 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 O8 O 0.0382(4) 0.4885(2) 0.25547(16) 0.0509(9) Uani 1 1 d . . . O1 O 1.1012(3) 0.12793(19) 0.17434(14) 0.0411(8) Uani 1 1 d . . . O2 O 0.9495(3) 0.22604(19) 0.09894(14) 0.0400(8) Uani 1 1 d . . . O3 O 0.9535(4) -0.0204(2) 0.23595(17) 0.0582(9) Uani 1 1 d . . . O4 O 0.7590(4) 0.3945(2) 0.20637(19) 0.0578(10) Uani 1 1 d . . . C9 C 0.9632(4) 0.1388(3) 0.1989(2) 0.0337(10) Uani 1 1 d . . . C16 C 0.8921(5) 0.2272(3) 0.1613(2) 0.0321(10) Uani 1 1 d . . . C21 C 1.1011(5) 0.1903(3) 0.1167(2) 0.0379(10) Uani 1 1 d . . . C14 C 0.6239(6) 0.2023(3) 0.0790(3) 0.0464(12) Uani 1 1 d . . . C11 C 0.8367(6) 0.0137(3) 0.1156(3) 0.0506(13) Uani 1 1 d . . . C15 C 0.7185(5) 0.2440(3) 0.1458(2) 0.0349(10) Uani 1 1 d . . . C17 C 0.6884(6) 0.3492(3) 0.1435(3) 0.0474(12) Uani 1 1 d . . . C19 C 1.1318(7) 0.1347(5) 0.0559(3) 0.0597(15) Uani 1 1 d . . . C13 C 0.5874(6) 0.0976(4) 0.0798(3) 0.0568(14) Uani 1 1 d . . . C20 C 1.2196(6) 0.2655(4) 0.1396(3) 0.0528(13) Uani 1 1 d . . . C12 C 0.7153(6) 0.0354(3) 0.0687(3) 0.0576(14) Uani 1 1 d . . . C10 C 0.8701(5) 0.0487(3) 0.1884(2) 0.0430(12) Uani 1 1 d . . . O5 O -0.1707(3) 0.6266(2) 0.17888(15) 0.0452(8) Uani 1 1 d . . . O7 O 0.1952(4) 0.8951(2) 0.19080(19) 0.0590(10) Uani 1 1 d . . . O6 O -0.0880(3) 0.7101(2) 0.09568(14) 0.0432(8) Uani 1 1 d . . . C1 C -0.0104(5) 0.6416(3) 0.2032(2) 0.0367(10) Uani 1 1 d . . . C3 C 0.0528(6) 0.5020(3) 0.1347(3) 0.0449(12) Uani 1 1 d . . . C7 C 0.1846(5) 0.7362(3) 0.1433(2) 0.0365(10) Uani 1 1 d . . . C8 C 0.0255(5) 0.7219(3) 0.1585(2) 0.0373(10) Uani 1 1 d . . . C22 C -0.2232(5) 0.6785(3) 0.1158(2) 0.0412(11) Uani 1 1 d . . . C2 C 0.0772(5) 0.5500(3) 0.2033(2) 0.0399(11) Uani 1 1 d . . . C5 C 0.2695(6) 0.5787(3) 0.0938(3) 0.0522(13) Uani 1 1 d . . . C23 C -0.3089(7) 0.6146(5) 0.0599(4) 0.0638(16) Uani 1 1 d . . . C6 C 0.2246(6) 0.6825(3) 0.0822(3) 0.0477(12) Uani 1 1 d . . . C4 C 0.1363(5) 0.5142(3) 0.0885(3) 0.0486(12) Uani 1 1 d . . . C24 C -0.3226(7) 0.7587(4) 0.1303(4) 0.0609(15) Uani 1 1 d . . . C18 C 0.2100(6) 0.8403(3) 0.1320(3) 0.0506(13) Uani 1 1 d . . . H26 H 0.990(3) 0.147(2) 0.2500(17) 0.018(9) Uiso 1 1 d . . . H24 H 0.673(4) 0.223(2) 0.1843(16) 0.020(9) Uiso 1 1 d . . . H9 H 0.253(4) 0.721(2) 0.1864(17) 0.016(9) Uiso 1 1 d . . . H12 H 0.139(5) 0.692(3) 0.042(2) 0.043(12) Uiso 1 1 d . . . H17 H 0.189(4) 0.564(2) 0.2194(17) 0.026(10) Uiso 1 1 d . . . H34 H 0.517(4) 0.231(2) 0.0712(16) 0.023(9) Uiso 1 1 d . . . H38 H 0.772(4) 0.058(3) 0.2033(17) 0.034(11) Uiso 1 1 d . . . H7 H 0.013(4) 0.657(3) 0.2540(19) 0.031(10) Uiso 1 1 d . . . H22 H 0.574(5) 0.362(3) 0.1330(19) 0.048(12) Uiso 1 1 d . . . H33 H 0.675(5) 0.214(3) 0.042(2) 0.062(15) Uiso 1 1 d . . . H10 H 0.136(5) 0.863(3) 0.090(2) 0.047(12) Uiso 1 1 d . . . H11 H 0.317(5) 0.854(3) 0.124(2) 0.052(13) Uiso 1 1 d . . . H19 H 0.317(6) 0.707(3) 0.071(2) 0.065(15) Uiso 1 1 d . . . H14 H 0.108(5) 0.486(3) 0.043(2) 0.057(14) Uiso 1 1 d . . . H23 H 0.729(5) 0.377(3) 0.102(2) 0.060(14) Uiso 1 1 d . . . H30 H 1.139(6) 0.173(4) 0.021(3) 0.09(2) Uiso 1 1 d . . . H27 H 1.218(4) 0.303(3) 0.099(2) 0.044(12) Uiso 1 1 d . . . H35 H 0.500(5) 0.086(3) 0.044(2) 0.064(15) Uiso 1 1 d . . . H31 H 1.226(6) 0.096(4) 0.073(3) 0.080(17) Uiso 1 1 d . . . H29 H 1.333(7) 0.238(4) 0.150(3) 0.092(18) Uiso 1 1 d . . . H13 H 0.331(5) 0.572(3) 0.144(2) 0.065(15) Uiso 1 1 d . . . H25 H 0.945(4) 0.277(3) 0.1907(18) 0.036(11) Uiso 1 1 d . . . H5 H -0.399(6) 0.587(3) 0.073(2) 0.068(16) Uiso 1 1 d . . . H15 H -0.037(6) 0.462(4) 0.128(2) 0.081(17) Uiso 1 1 d . . . H1 H -0.415(5) 0.731(3) 0.145(2) 0.061(15) Uiso 1 1 d . . . H3 H -0.366(5) 0.790(3) 0.085(2) 0.058(14) Uiso 1 1 d . . . H21 H 0.912(5) -0.018(3) 0.104(2) 0.047(13) Uiso 1 1 d . . . H40 H 0.700(5) 0.019(3) 0.020(2) 0.055(14) Uiso 1 1 d . . . H32 H 1.054(5) 0.090(3) 0.043(2) 0.057(15) Uiso 1 1 d . . . H39 H -0.271(6) 0.796(4) 0.167(3) 0.09(2) Uiso 1 1 d . . . H36 H 0.549(5) 0.079(3) 0.126(2) 0.053(13) Uiso 1 1 d . . . H37 H 1.040(6) -0.045(4) 0.215(2) 0.072(16) Uiso 1 1 d . . . H4 H -0.246(6) 0.570(4) 0.051(3) 0.08(2) Uiso 1 1 d . . . H20 H 0.678(6) 0.422(4) 0.224(3) 0.10(2) Uiso 1 1 d . . . H2 H 0.334(5) 0.560(3) 0.060(2) 0.065(14) Uiso 1 1 d . . . H6 H -0.352(7) 0.649(4) 0.018(3) 0.10(2) Uiso 1 1 d . . . H8 H 0.004(4) 0.774(3) 0.1801(19) 0.044(13) Uiso 1 1 d . . . H28 H 1.205(6) 0.297(4) 0.182(3) 0.077(18) Uiso 1 1 d . . . H16 H -0.061(5) 0.461(3) 0.236(2) 0.059(14) Uiso 1 1 d . . . H18 H 0.287(6) 0.926(4) 0.205(3) 0.09(2) 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 O8 0.0457(19) 0.0406(19) 0.063(2) 0.0199(16) 0.0036(16) -0.0027(16) O1 0.0374(17) 0.0286(17) 0.0569(18) 0.0101(14) 0.0089(14) 0.0082(13) O2 0.0380(17) 0.0346(17) 0.0494(18) 0.0091(14) 0.0135(14) 0.0086(13) O3 0.056(2) 0.0356(19) 0.089(2) 0.0285(17) 0.0297(19) 0.0117(16) O4 0.048(2) 0.0327(19) 0.096(3) -0.0225(18) 0.0225(19) -0.0022(16) C9 0.033(2) 0.024(2) 0.042(3) 0.0014(19) 0.003(2) 0.0036(18) C16 0.037(2) 0.023(2) 0.036(2) -0.0022(19) 0.0082(19) -0.0016(19) C21 0.034(2) 0.031(2) 0.050(3) 0.004(2) 0.012(2) 0.005(2) C14 0.037(3) 0.044(3) 0.058(3) -0.006(2) 0.008(2) 0.002(2) C11 0.048(3) 0.019(3) 0.087(4) -0.015(2) 0.018(3) -0.004(2) C15 0.042(3) 0.023(2) 0.043(3) 0.0010(19) 0.016(2) 0.0022(19) C17 0.042(3) 0.026(3) 0.075(4) 0.000(2) 0.014(3) 0.010(2) C19 0.056(4) 0.062(4) 0.064(4) 0.000(3) 0.019(3) 0.008(3) C13 0.043(3) 0.045(3) 0.076(4) -0.017(3) -0.003(3) -0.010(2) C20 0.048(3) 0.034(3) 0.076(4) 0.011(3) 0.012(3) -0.007(2) C12 0.049(3) 0.043(3) 0.076(4) -0.023(3) 0.003(3) -0.005(3) C10 0.036(3) 0.030(3) 0.066(3) 0.011(2) 0.016(2) 0.004(2) O5 0.0376(17) 0.0387(18) 0.0595(19) 0.0123(15) 0.0108(14) -0.0014(14) O7 0.051(2) 0.0290(19) 0.097(3) -0.0117(18) 0.015(2) -0.0064(16) O6 0.0335(16) 0.0404(19) 0.0534(19) 0.0108(14) 0.0039(14) -0.0003(14) C1 0.038(3) 0.030(3) 0.041(3) -0.003(2) 0.006(2) -0.0036(19) C3 0.042(3) 0.026(3) 0.065(3) -0.001(2) 0.008(3) 0.000(2) C7 0.034(2) 0.028(2) 0.045(3) 0.003(2) 0.003(2) -0.0043(19) C8 0.040(3) 0.024(3) 0.046(3) 0.001(2) 0.007(2) 0.001(2) C22 0.031(2) 0.036(3) 0.055(3) 0.006(2) 0.006(2) 0.002(2) C2 0.035(3) 0.030(3) 0.053(3) 0.008(2) 0.004(2) 0.002(2) C5 0.047(3) 0.049(3) 0.064(4) -0.010(3) 0.020(3) 0.000(2) C23 0.039(3) 0.072(5) 0.077(4) -0.014(4) 0.004(3) -0.009(3) C6 0.045(3) 0.044(3) 0.054(3) 0.001(2) 0.012(3) -0.008(2) C4 0.052(3) 0.030(3) 0.062(3) -0.013(2) 0.007(3) 0.006(2) C24 0.053(4) 0.048(4) 0.076(4) 0.004(3) 0.002(3) 0.016(3) C18 0.049(3) 0.035(3) 0.065(4) 0.009(3) 0.006(3) -0.010(2) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 O8 C2 1.450(5) . ? O1 C9 1.420(5) . ? O1 C21 1.443(5) . ? O2 C21 1.415(5) . ? O2 C16 1.424(4) . ? O3 C10 1.454(5) . ? O4 C17 1.419(6) . ? C9 C10 1.525(6) . ? C9 C16 1.535(5) . ? C16 C15 1.529(6) . ? C21 C20 1.508(6) . ? C21 C19 1.510(7) . ? C14 C15 1.523(6) . ? C14 C13 1.537(7) . ? C11 C12 1.300(7) . ? C11 C10 1.484(7) . ? C15 C17 1.532(6) . ? C13 C12 1.498(7) . ? O5 C1 1.421(5) . ? O5 C22 1.436(5) . ? O7 C18 1.427(6) . ? O6 C22 1.419(5) . ? O6 C8 1.429(5) . ? C1 C8 1.523(6) . ? C1 C2 1.527(6) . ? C3 C4 1.302(6) . ? C3 C2 1.488(6) . ? C7 C8 1.521(6) . ? C7 C6 1.531(6) . ? C7 C18 1.532(6) . ? C22 C23 1.508(7) . ? C22 C24 1.514(7) . ? C5 C4 1.490(7) . ? C5 C6 1.545(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C9 O1 C21 110.0(3) . . ? C21 O2 C16 106.8(3) . . ? O1 C9 C10 110.2(3) . . ? O1 C9 C16 103.0(3) . . ? C10 C9 C16 118.5(3) . . ? O2 C16 C15 111.3(3) . . ? O2 C16 C9 102.6(3) . . ? C15 C16 C9 121.4(3) . . ? O2 C21 O1 105.1(3) . . ? O2 C21 C20 112.6(4) . . ? O1 C21 C20 109.0(4) . . ? O2 C21 C19 108.6(4) . . ? O1 C21 C19 108.9(4) . . ? C20 C21 C19 112.4(4) . . ? C15 C14 C13 117.0(4) . . ? C12 C11 C10 124.7(5) . . ? C14 C15 C16 117.4(4) . . ? C14 C15 C17 107.4(4) . . ? C16 C15 C17 108.9(3) . . ? O4 C17 C15 112.5(4) . . ? C12 C13 C14 114.3(4) . . ? C11 C12 C13 125.5(5) . . ? O3 C10 C11 111.0(4) . . ? O3 C10 C9 107.6(3) . . ? C11 C10 C9 114.2(4) . . ? C1 O5 C22 109.4(3) . . ? C22 O6 C8 106.4(3) . . ? O5 C1 C8 103.8(3) . . ? O5 C1 C2 110.2(3) . . ? C8 C1 C2 118.8(4) . . ? C4 C3 C2 125.1(5) . . ? C8 C7 C6 117.8(4) . . ? C8 C7 C18 109.4(4) . . ? C6 C7 C18 108.0(4) . . ? O6 C8 C7 111.2(3) . . ? O6 C8 C1 102.3(3) . . ? C7 C8 C1 122.2(4) . . ? O6 C22 O5 105.5(3) . . ? O6 C22 C23 108.6(4) . . ? O5 C22 C23 109.6(4) . . ? O6 C22 C24 111.9(4) . . ? O5 C22 C24 109.1(4) . . ? C23 C22 C24 112.0(5) . . ? O8 C2 C3 110.4(4) . . ? O8 C2 C1 109.0(3) . . ? C3 C2 C1 114.9(4) . . ? C4 C5 C6 114.3(4) . . ? C7 C6 C5 117.7(4) . . ? C3 C4 C5 126.7(5) . . ? O7 C18 C7 112.1(4) . . ? data_kp2 _database_code_CSD 193887 _audit_creation_date 2002-09-11T22:06:35-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; (3aS*,4R*,6S*,9R*,9aS*)-4-(acetyloxy)-9-[(acetyloxy)methyl]-2,2- dimethylperhydro cycloocta[d][1,3]dioxol-6-yl acetate ; _chemical_formula_sum 'C18 H28 O8' _chemical_formula_weight 372.4 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _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 7.7179(16) _cell_length_b 11.486(2) _cell_length_c 11.720(2) _cell_angle_alpha 76.515(4) _cell_angle_beta 74.547(4) _cell_angle_gamma 85.394(4) _cell_volume 973.6(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_density_diffrn 1.27 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 400 _exptl_special_details ? _exptl_crystal_description rectangular _exptl_crystal_colour colourless _exptl_crystal_size_max .250 _exptl_crystal_size_mid .140 _exptl_crystal_size_min .105 #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.1 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_reflns_av_unetI/netI 0.0927 _diffrn_reflns_number 10725 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 27.7 _diffrn_reflns_theta_full 27.7 _diffrn_measured_fraction_theta_full 0.915 _diffrn_measured_fraction_theta_max 0.915 _reflns_number_total 4173 _reflns_number_gt 2082 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0494P)^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_number_reflns 4173 _refine_ls_number_parameters 347 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1189 _refine_ls_R_factor_gt 0.0531 _refine_ls_wR_factor_ref 0.1183 _refine_ls_wR_factor_gt 0.0985 _refine_ls_goodness_of_fit_ref 0.881 _refine_ls_restrained_S_all 0.881 _refine_ls_shift/su_max 0.014 _refine_ls_shift/su_mean 0.001 _refine_diff_density_max 0.213 _refine_diff_density_min -0.167 _refine_diff_density_rms 0.046 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 H28 H -0.014(6) 1.251(4) 0.735(4) 0.18(2) Uiso 1 1 d . . . H27 H 0.485(5) 0.735(3) 0.563(3) 0.142(14) Uiso 1 1 d . . . H26 H 0.877(5) 0.897(3) 0.571(3) 0.133(14) Uiso 1 1 d . . . H25 H 0.699(5) 0.732(3) 0.532(3) 0.139(15) Uiso 1 1 d . . . H22 H -0.096(5) 0.456(4) 0.731(3) 0.152(17) Uiso 1 1 d . . . H23 H -0.217(7) 0.565(5) 0.717(5) 0.21(2) Uiso 1 1 d . . . H24 H -0.075(5) 1.196(3) 0.663(4) 0.134(17) Uiso 1 1 d . . . H20 H 0.615(4) 0.587(3) 1.384(3) 0.107(12) Uiso 1 1 d . . . H21 H 0.500(5) 0.521(4) 1.338(3) 0.152(19) Uiso 1 1 d . . . H19 H 0.435(5) 0.631(3) 1.370(3) 0.126(14) Uiso 1 1 d . . . H11 H -0.099(4) 0.517(3) 0.613(3) 0.120(14) Uiso 1 1 d . . . H12 H 0.765(3) 0.996(2) 0.642(3) 0.092(10) Uiso 1 1 d . . . H17 H 0.365(3) 0.8148(17) 1.0008(18) 0.048(6) Uiso 1 1 d . . . H18 H 0.663(3) 0.815(2) 1.0147(18) 0.058(7) Uiso 1 1 d . . . H13 H 0.762(4) 0.996(3) 0.515(3) 0.096(10) Uiso 1 1 d . . . H15 H 0.448(3) 0.6120(19) 0.896(2) 0.058(7) Uiso 1 1 d . . . H16 H 0.364(3) 0.6014(18) 1.037(2) 0.053(6) Uiso 1 1 d . . . H14 H 0.601(3) 0.840(2) 0.458(2) 0.080(8) Uiso 1 1 d . . . H3 H -0.199(4) 1.221(3) 0.765(3) 0.107(11) Uiso 1 1 d . . . H5 H -0.021(3) 0.8289(18) 0.8091(18) 0.054(6) Uiso 1 1 d . . . H1 H 0.137(3) 0.576(2) 0.964(2) 0.060(7) Uiso 1 1 d . . . H10 H 0.686(3) 0.686(2) 0.9809(19) 0.057(7) Uiso 1 1 d . . . H4 H 0.285(3) 0.6825(17) 0.7524(17) 0.048(6) Uiso 1 1 d . . . H8 H 0.606(3) 0.8964(17) 0.8337(17) 0.043(6) Uiso 1 1 d . . . H6 H 0.126(3) 0.8498(17) 0.6860(19) 0.045(6) Uiso 1 1 d . . . H2 H 0.095(3) 0.701(2) 0.992(2) 0.068(8) Uiso 1 1 d . . . H9 H 0.417(2) 1.0149(16) 0.7736(15) 0.031(5) Uiso 1 1 d . . . H7 H 0.152(2) 0.9120(14) 0.9012(16) 0.028(5) Uiso 1 1 d . . . O4 O 0.11929(18) 1.03724(12) 0.75659(12) 0.0488(4) Uani 1 1 d . . . O2 O 0.44620(18) 0.92799(14) 0.64592(12) 0.0531(4) Uani 1 1 d . . . O3 O 0.0313(2) 0.62494(13) 0.79315(15) 0.0568(4) Uani 1 1 d . . . O5 O 0.5276(2) 0.68288(16) 1.14188(13) 0.0696(5) Uani 1 1 d . . . O9 O -0.1418(2) 1.01812(15) 0.89949(15) 0.0643(5) Uani 1 1 d . . . O1 O 0.5986(2) 0.78044(14) 0.74133(13) 0.0615(5) Uani 1 1 d . . . C2 C 0.1876(3) 0.92112(19) 0.8131(2) 0.0419(5) Uani 1 1 d . . . C8 C 0.5177(3) 0.8483(2) 0.83036(19) 0.0467(6) Uani 1 1 d . . . C1 C 0.3893(3) 0.9362(2) 0.76899(19) 0.0417(5) Uani 1 1 d . . . C3 C 0.1057(3) 0.8274(2) 0.7735(2) 0.0464(6) Uani 1 1 d . . . C4 C 0.1669(3) 0.69813(19) 0.8084(2) 0.0453(5) Uani 1 1 d . . . C17 C -0.0458(3) 1.0739(2) 0.8080(2) 0.0495(6) Uani 1 1 d . . . C12 C 0.6079(3) 0.8585(2) 0.62585(19) 0.0515(6) Uani 1 1 d . . . C7 C 0.4484(3) 0.7668(2) 0.95532(19) 0.0449(6) Uani 1 1 d . . . O7 O 0.1537(3) 0.65218(19) 0.59349(18) 0.0883(6) Uani 1 1 d . . . C6 C 0.3652(3) 0.6501(2) 0.9583(2) 0.0542(6) Uani 1 1 d . . . C5 C 0.1766(3) 0.6536(3) 0.9388(2) 0.0549(7) Uani 1 1 d . . . O6 O 0.7938(3) 0.6690(2) 1.17755(18) 0.1135(9) Uani 1 1 d . . . C13 C 0.6362(4) 0.6524(2) 1.2134(2) 0.0588(7) Uani 1 1 d . . . C9 C 0.6027(3) 0.7410(3) 1.0163(2) 0.0597(7) Uani 1 1 d . . . C15 C 0.0406(4) 0.6092(2) 0.6825(3) 0.0610(7) Uani 1 1 d . . . C10 C 0.7680(4) 0.9374(4) 0.5856(3) 0.0803(10) Uani 1 1 d . . . C18 C -0.0920(5) 1.1912(3) 0.7354(4) 0.0733(9) Uani 1 1 d . . . C14 C 0.5430(5) 0.5920(4) 1.3384(3) 0.0781(10) Uani 1 1 d . . . C11 C 0.6025(6) 0.7866(3) 0.5356(3) 0.0827(10) Uani 1 1 d . . . C16 C -0.1081(6) 0.5319(3) 0.6871(4) 0.0830(10) 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 O4 0.0433(9) 0.0453(9) 0.0491(9) -0.0031(7) -0.0066(7) 0.0106(7) O2 0.0412(9) 0.0719(11) 0.0362(9) 0.0020(7) -0.0085(7) 0.0119(8) O3 0.0567(10) 0.0537(10) 0.0600(11) -0.0061(8) -0.0171(8) -0.0122(8) O5 0.0466(10) 0.1126(15) 0.0396(10) 0.0114(9) -0.0182(8) -0.0034(9) O9 0.0510(10) 0.0702(12) 0.0617(11) -0.0141(9) -0.0003(9) 0.0081(9) O1 0.0585(10) 0.0683(11) 0.0379(9) 0.0064(8) -0.0013(7) 0.0228(8) C2 0.0421(13) 0.0416(13) 0.0359(13) 0.0007(10) -0.0098(10) 0.0057(10) C8 0.0391(13) 0.0562(15) 0.0419(13) 0.0002(11) -0.0142(10) -0.0033(12) C1 0.0421(13) 0.0395(14) 0.0410(13) -0.0017(10) -0.0120(10) -0.0029(10) C3 0.0388(14) 0.0471(15) 0.0503(15) -0.0026(12) -0.0133(11) -0.0014(11) C4 0.0410(13) 0.0447(14) 0.0465(14) -0.0027(11) -0.0096(11) -0.0058(11) C17 0.0441(14) 0.0528(15) 0.0539(15) -0.0174(12) -0.0142(12) 0.0088(11) C12 0.0407(13) 0.0630(16) 0.0376(13) 0.0083(12) -0.0066(10) 0.0065(11) C7 0.0363(12) 0.0591(16) 0.0333(12) 0.0002(11) -0.0091(10) 0.0034(11) O7 0.0913(15) 0.1128(17) 0.0630(13) -0.0280(12) -0.0108(11) -0.0190(13) C6 0.0541(15) 0.0562(17) 0.0431(15) 0.0070(13) -0.0143(12) 0.0040(12) C5 0.0545(16) 0.0508(17) 0.0509(16) 0.0066(13) -0.0119(12) -0.0095(13) O6 0.0603(13) 0.199(3) 0.0697(13) 0.0101(14) -0.0284(11) -0.0107(14) C13 0.0522(16) 0.0778(18) 0.0458(15) -0.0063(13) -0.0198(13) 0.0065(13) C9 0.0458(15) 0.083(2) 0.0421(15) 0.0073(14) -0.0142(12) -0.0033(16) C15 0.0669(18) 0.0528(16) 0.0679(19) -0.0145(14) -0.0260(15) 0.0056(14) C10 0.0513(19) 0.119(3) 0.0562(19) 0.015(2) -0.0128(15) -0.0243(19) C18 0.069(2) 0.059(2) 0.082(3) -0.0088(18) -0.0174(18) 0.0250(17) C14 0.079(2) 0.110(3) 0.0421(17) 0.0009(17) -0.0247(16) -0.001(2) C11 0.116(3) 0.077(2) 0.0394(17) -0.0049(16) -0.0026(17) 0.004(2) C16 0.096(3) 0.063(2) 0.109(3) -0.024(2) -0.053(2) -0.0096(19) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 O4 C17 1.337(2) . ? O4 C2 1.468(2) . ? O2 C1 1.415(2) . ? O2 C12 1.422(2) . ? O3 C15 1.333(3) . ? O3 C4 1.465(2) . ? O5 C13 1.311(3) . ? O5 C9 1.448(3) . ? O9 C17 1.201(2) . ? O1 C12 1.426(2) . ? O1 C8 1.428(3) . ? C2 C3 1.506(3) . ? C2 C1 1.515(3) . ? C8 C7 1.527(3) . ? C8 C1 1.549(3) . ? C3 C4 1.518(3) . ? C4 C5 1.514(3) . ? C17 C18 1.489(4) . ? C12 C11 1.496(4) . ? C12 C10 1.496(4) . ? C7 C6 1.521(3) . ? C7 C9 1.522(3) . ? O7 C15 1.199(3) . ? C6 C5 1.528(3) . ? O6 C13 1.191(3) . ? C13 C14 1.479(4) . ? C15 C16 1.489(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 C17 O4 C2 118.71(16) . . ? C1 O2 C12 110.09(15) . . ? C15 O3 C4 118.72(18) . . ? C13 O5 C9 118.35(18) . . ? C12 O1 C8 106.58(16) . . ? O4 C2 C3 106.24(17) . . ? O4 C2 C1 102.42(16) . . ? C3 C2 C1 117.92(19) . . ? O1 C8 C7 111.32(19) . . ? O1 C8 C1 103.09(17) . . ? C7 C8 C1 121.02(18) . . ? O2 C1 C2 109.10(18) . . ? O2 C1 C8 103.83(16) . . ? C2 C1 C8 120.69(18) . . ? C2 C3 C4 118.07(19) . . ? O3 C4 C5 105.48(17) . . ? O3 C4 C3 106.18(17) . . ? C5 C4 C3 116.2(2) . . ? O9 C17 O4 123.8(2) . . ? O9 C17 C18 125.7(2) . . ? O4 C17 C18 110.5(2) . . ? O2 C12 O1 103.53(15) . . ? O2 C12 C11 108.3(2) . . ? O1 C12 C11 109.5(2) . . ? O2 C12 C10 110.5(2) . . ? O1 C12 C10 111.9(2) . . ? C11 C12 C10 112.6(3) . . ? C6 C7 C9 110.0(2) . . ? C6 C7 C8 116.4(2) . . ? C9 C7 C8 107.93(18) . . ? C7 C6 C5 118.9(2) . . ? C4 C5 C6 114.9(2) . . ? O6 C13 O5 122.0(2) . . ? O6 C13 C14 125.1(3) . . ? O5 C13 C14 112.8(3) . . ? O5 C9 C7 107.23(19) . . ? O7 C15 O3 123.8(2) . . ? O7 C15 C16 126.1(3) . . ? O3 C15 C16 110.1(3) . . ? data_kp4o_m _database_code_CSD 193888 _audit_creation_date 2002-09-11T22:17:48-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; (3aS*,4S*,5S*,9R*,9aS*)-4-(acetyloxy)-9-[(acetyloxy)methyl]-2,2- dimethylperhydro cycloocta[d][1,3]dioxol-5-ylacetate ; _chemical_formula_sum 'C19 H28 O10' _chemical_formula_weight 416.41 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'Pccn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z' '-x, y+1/2, -z+1/2' 'x+1/2, -y, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z' 'x, -y-1/2, z-1/2' '-x-1/2, y, z-1/2' _cell_length_a 19.053(9) _cell_length_b 26.424(12) _cell_length_c 7.686(4) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 3870(3) _cell_formula_units_Z 7 _cell_measurement_temperature 293(2) #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_density_diffrn 1.251 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1554 _exptl_special_details ? _exptl_crystal_description 'thick plate' _exptl_crystal_colour colourless _exptl_crystal_size_max .890 _exptl_crystal_size_mid .132 _exptl_crystal_size_min .080 #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_reflns_av_unetI/netI 0.0472 _diffrn_reflns_number 29110 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -33 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.32 _diffrn_reflns_theta_max 26.38 _diffrn_reflns_theta_full 26.38 _diffrn_measured_fraction_theta_full 1 _diffrn_measured_fraction_theta_max 1 _reflns_number_total 3965 _reflns_number_gt 2836 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0866P)^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_number_reflns 3965 _refine_ls_number_parameters 347 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0665 _refine_ls_R_factor_gt 0.0483 _refine_ls_wR_factor_ref 0.1359 _refine_ls_wR_factor_gt 0.1261 _refine_ls_goodness_of_fit_ref 0.991 _refine_ls_restrained_S_all 0.991 _refine_ls_shift/su_max 0.114 _refine_ls_shift/su_mean 0.009 _refine_diff_density_max 0.234 _refine_diff_density_min -0.273 _refine_diff_density_rms 0.057 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 H28 H 0.167(2) 0.4449(13) 0.440(5) 0.156(13) Uiso 1 1 d . . . H27 H 0.2464(17) 0.6601(10) 0.853(4) 0.127(9) Uiso 1 1 d . . . H25 H 0.232(2) 0.4699(13) 0.503(6) 0.173(15) Uiso 1 1 d . . . H26 H 0.2263(19) 0.4475(14) 0.330(5) 0.155(14) Uiso 1 1 d . . . H24 H 0.0648(8) 0.5846(6) 0.909(2) 0.043(4) Uiso 1 1 d . . . H23 H 0.1277(7) 0.5871(5) 0.6857(18) 0.035(4) Uiso 1 1 d . . . O3 O 0.12827(5) 0.66096(4) 0.66892(13) 0.0440(3) Uani 1 1 d . . . O1 O 0.13482(6) 0.53582(4) 0.42389(14) 0.0527(3) Uani 1 1 d . . . O4 O 0.07694(5) 0.65852(5) 0.93127(14) 0.0536(3) Uani 1 1 d . . . O5 O -0.05129(6) 0.59482(4) 1.00990(14) 0.0502(3) Uani 1 1 d . . . O7 O -0.13702(5) 0.65597(5) 0.82123(16) 0.0555(3) Uani 1 1 d . . . C3 C 0.05191(8) 0.61440(6) 0.84496(18) 0.0416(3) Uani 1 1 d . . . C5 C -0.06162(8) 0.66597(6) 0.8268(2) 0.0456(4) Uani 1 1 d . . . C2 C 0.09323(7) 0.61328(6) 0.67107(17) 0.0387(3) Uani 1 1 d . . . C4 C -0.02784(8) 0.61454(6) 0.84313(18) 0.0422(4) Uani 1 1 d . . . C12 C 0.13927(8) 0.67492(6) 0.8451(2) 0.0471(4) Uani 1 1 d . . . C7 C -0.04976(9) 0.66788(8) 0.4935(2) 0.0557(4) Uani 1 1 d . . . C8 C 0.01874(9) 0.64889(7) 0.4138(2) 0.0519(4) Uani 1 1 d . . . C1 C 0.05599(8) 0.60393(6) 0.49729(18) 0.0427(4) Uani 1 1 d . . . C6 C -0.04258(9) 0.69584(7) 0.6666(2) 0.0527(4) Uani 1 1 d . . . C10 C 0.18886(10) 0.51606(7) 0.3358(2) 0.0617(5) Uani 1 1 d . . . C14 C 0.20273(10) 0.64905(11) 0.9211(3) 0.0670(5) Uani 1 1 d . . . C15 C -0.06999(9) 0.54659(7) 1.0193(2) 0.0535(4) Uani 1 1 d . . . O6 O -0.06801(9) 0.51822(5) 0.89739(19) 0.0875(5) Uani 1 1 d . . . C17 C -0.17832(9) 0.68324(7) 0.9239(2) 0.0574(4) Uani 1 1 d . . . O2 O 0.21803(9) 0.53786(6) 0.2210(2) 0.0984(6) Uani 1 1 d . . . C9 C 0.10924(10) 0.58421(7) 0.3660(2) 0.0515(4) Uani 1 1 d . . . O8 O -0.15738(7) 0.71439(7) 1.0217(3) 0.1041(6) Uani 1 1 d . . . C13 C 0.14357(13) 0.73179(9) 0.8548(4) 0.0731(6) Uani 1 1 d . . . C18 C -0.25377(11) 0.66951(13) 0.9021(4) 0.0773(7) Uani 1 1 d . . . C11 C 0.20627(15) 0.46462(10) 0.3993(4) 0.0762(6) Uani 1 1 d . . . C16 C -0.09029(15) 0.53266(11) 1.2003(3) 0.0809(7) Uani 1 1 d . . . H13 H -0.0435(7) 0.5921(5) 0.756(2) 0.034(4) Uiso 1 1 d . . . H15 H 0.0885(9) 0.5789(6) 0.255(3) 0.056(5) Uiso 1 1 d . . . H14 H 0.0222(9) 0.5750(6) 0.5151(19) 0.044(4) Uiso 1 1 d . . . H12 H -0.0730(10) 0.7280(7) 0.671(2) 0.063(5) Uiso 1 1 d . . . H10 H 0.0081(8) 0.6388(6) 0.293(2) 0.051(4) Uiso 1 1 d . . . H9 H 0.0525(9) 0.6782(6) 0.406(2) 0.051(5) Uiso 1 1 d . . . H22 H -0.0532(7) 0.6848(5) 0.928(2) 0.037(4) Uiso 1 1 d . . . H11 H 0.0048(10) 0.7075(7) 0.682(2) 0.062(5) Uiso 1 1 d . . . H16 H 0.1478(10) 0.6074(7) 0.354(2) 0.061(5) Uiso 1 1 d . . . H8 H -0.0835(9) 0.6374(7) 0.508(2) 0.056(5) Uiso 1 1 d . . . H7 H -0.0678(10) 0.6924(7) 0.403(2) 0.063(5) Uiso 1 1 d . . . H21 H 0.2081(11) 0.6575(9) 1.049(3) 0.094(7) Uiso 1 1 d . . . H20 H 0.2005(10) 0.6132(9) 0.919(3) 0.073(6) Uiso 1 1 d . . . H17 H 0.1010(13) 0.7493(8) 0.796(3) 0.103(8) Uiso 1 1 d . . . H19 H 0.1470(11) 0.7413(10) 0.970(4) 0.097(8) Uiso 1 1 d . . . H4 H -0.2758(16) 0.6832(10) 0.984(4) 0.106(9) Uiso 1 1 d . . . H5 H -0.2620(16) 0.6377(12) 0.852(4) 0.130(11) Uiso 1 1 d . . . H3 H -0.0490(16) 0.5193(11) 1.257(4) 0.119(10) Uiso 1 1 d . . . H6 H -0.2677(18) 0.6856(13) 0.814(5) 0.144(14) Uiso 1 1 d . . . H2 H -0.1227(14) 0.5061(10) 1.200(3) 0.105(8) Uiso 1 1 d . . . H18 H 0.1810(15) 0.7435(11) 0.777(4) 0.130(10) Uiso 1 1 d . . . H1 H -0.1139(15) 0.5648(11) 1.254(4) 0.130(10) 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 O3 0.0438(6) 0.0495(6) 0.0388(6) -0.0044(4) 0.0003(4) -0.0090(5) O1 0.0561(7) 0.0564(7) 0.0457(6) -0.0114(5) 0.0128(5) -0.0012(5) O4 0.0383(6) 0.0793(8) 0.0433(6) -0.0204(5) 0.0039(4) -0.0065(5) O5 0.0566(7) 0.0482(7) 0.0457(6) -0.0034(5) 0.0152(5) -0.0084(5) O7 0.0329(6) 0.0680(8) 0.0656(8) -0.0159(6) 0.0020(5) -0.0013(5) C3 0.0422(8) 0.0474(9) 0.0353(7) 0.0014(7) 0.0012(6) 0.0041(7) C5 0.0311(7) 0.0515(9) 0.0542(10) -0.0066(7) -0.0002(6) -0.0015(6) C2 0.0361(7) 0.0410(8) 0.0389(8) -0.0021(6) 0.0020(6) 0.0025(6) C4 0.0406(8) 0.0486(9) 0.0373(8) -0.0034(7) 0.0046(6) -0.0046(7) C12 0.0376(8) 0.0629(10) 0.0407(8) -0.0117(7) 0.0002(6) -0.0011(7) C7 0.0472(9) 0.0645(12) 0.0553(10) 0.0108(9) -0.0103(8) 0.0035(9) C8 0.0522(9) 0.0639(11) 0.0396(9) 0.0069(8) -0.0045(7) -0.0058(8) C1 0.0420(8) 0.0495(9) 0.0368(8) -0.0030(6) 0.0016(6) -0.0085(7) C6 0.0430(9) 0.0495(10) 0.0658(11) 0.0045(8) -0.0033(7) 0.0028(8) C10 0.0598(11) 0.0657(12) 0.0596(11) -0.0227(9) 0.0184(9) -0.0098(9) C14 0.0448(10) 0.0953(18) 0.0611(12) -0.0034(11) -0.0101(9) 0.0056(10) C15 0.0454(9) 0.0559(11) 0.0592(10) 0.0027(8) -0.0011(7) -0.0127(7) O6 0.1313(14) 0.0625(9) 0.0686(9) -0.0057(7) -0.0144(9) -0.0329(8) C17 0.0418(9) 0.0662(11) 0.0644(10) -0.0100(9) 0.0052(8) -0.0003(8) O2 0.1022(12) 0.0823(10) 0.1107(12) -0.0072(9) 0.0669(10) -0.0051(8) C9 0.0579(10) 0.0566(11) 0.0401(8) -0.0059(7) 0.0086(8) -0.0094(9) O8 0.0537(8) 0.1238(13) 0.1348(15) -0.0734(12) 0.0166(8) -0.0096(8) C13 0.0731(14) 0.0675(13) 0.0787(15) -0.0246(11) -0.0147(12) -0.0072(11) C18 0.0388(10) 0.1067(19) 0.0864(18) -0.0207(16) 0.0067(11) 0.0007(11) C11 0.0780(15) 0.0763(16) 0.0744(14) -0.0150(12) 0.0121(13) 0.0130(12) C16 0.0828(16) 0.0787(16) 0.0812(15) 0.0176(12) 0.0265(13) -0.0174(14) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 O3 C12 1.4192(19) . ? O3 C2 1.4260(18) . ? O1 C10 1.338(2) . ? O1 C9 1.439(2) . ? O4 C3 1.4236(19) . ? O4 C12 1.4271(19) . ? O5 C15 1.325(2) . ? O5 C4 1.4540(18) . ? O7 C17 1.327(2) . ? O7 C5 1.4612(19) . ? C3 C4 1.520(2) . ? C3 C2 1.552(2) . ? C5 C6 1.507(2) . ? C5 C4 1.509(2) . ? C2 C1 1.533(2) . ? C12 C14 1.507(2) . ? C12 C13 1.507(3) . ? C7 C8 1.527(3) . ? C7 C6 1.528(3) . ? C8 C1 1.526(2) . ? C1 C9 1.523(2) . ? C10 O2 1.192(2) . ? C10 C11 1.482(3) . ? C15 O6 1.201(2) . ? C15 C16 1.490(3) . ? C17 O8 1.184(2) . ? C17 C18 1.492(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 C12 O3 C2 106.72(11) . . ? C10 O1 C9 116.81(14) . . ? C3 O4 C12 108.14(11) . . ? C15 O5 C4 118.37(12) . . ? C17 O7 C5 117.86(13) . . ? O4 C3 C4 109.71(12) . . ? O4 C3 C2 104.29(11) . . ? C4 C3 C2 119.97(12) . . ? O7 C5 C6 107.90(13) . . ? O7 C5 C4 105.01(12) . . ? C6 C5 C4 115.92(14) . . ? O3 C2 C1 110.44(11) . . ? O3 C2 C3 103.35(11) . . ? C1 C2 C3 121.25(12) . . ? O5 C4 C5 105.37(12) . . ? O5 C4 C3 107.35(11) . . ? C5 C4 C3 115.44(13) . . ? O3 C12 O4 103.95(11) . . ? O3 C12 C14 111.75(14) . . ? O4 C12 C14 110.49(16) . . ? O3 C12 C13 108.33(16) . . ? O4 C12 C13 108.98(15) . . ? C14 C12 C13 112.93(17) . . ? C8 C7 C6 115.60(14) . . ? C1 C8 C7 118.99(14) . . ? C9 C1 C8 107.32(13) . . ? C9 C1 C2 108.91(13) . . ? C8 C1 C2 117.17(13) . . ? C5 C6 C7 115.88(15) . . ? O2 C10 O1 123.01(19) . . ? O2 C10 C11 125.67(19) . . ? O1 C10 C11 111.32(17) . . ? O6 C15 O5 123.34(16) . . ? O6 C15 C16 125.62(19) . . ? O5 C15 C16 110.99(17) . . ? O8 C17 O7 123.73(16) . . ? O8 C17 C18 124.41(19) . . ? O7 C17 C18 111.85(18) . . ? O1 C9 C1 108.98(13) . . ? data_kp3_m _database_code_CSD 193889 _audit_creation_date 2002-09-11T22:12:52-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; [(1R*,2S*,3S*,4R*,5S*,6S*)-2,3,4,5,6-penta(acetyloxy)cyclooctyl]methyl acetate ; _chemical_formula_sum 'C21 H30 O12' _chemical_formula_weight 474.45 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P2(1)/c' 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 14.228(3) _cell_length_b 7.9506(16) _cell_length_c 22.162(5) _cell_angle_alpha 90 _cell_angle_beta 107.296(3) _cell_angle_gamma 90 _cell_volume 2393.6(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_density_diffrn 1.317 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1008 _exptl_special_details ? _exptl_crystal_description rhombohedral _exptl_crystal_colour colourless _exptl_crystal_size_max .475 _exptl_crystal_size_mid .175 _exptl_crystal_size_min .160 #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.109 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_reflns_av_unetI/netI 0.0684 _diffrn_reflns_number 18435 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.5 _diffrn_reflns_theta_max 26.37 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _reflns_number_total 4872 _reflns_number_gt 3649 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0911P)^2^+0.3492P] 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_number_reflns 4872 _refine_ls_number_parameters 304 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0762 _refine_ls_R_factor_gt 0.0609 _refine_ls_wR_factor_ref 0.1761 _refine_ls_wR_factor_gt 0.1644 _refine_ls_goodness_of_fit_ref 1.05 _refine_ls_restrained_S_all 1.05 _refine_ls_shift/su_max 0.26 _refine_ls_shift/su_mean 0.007 _refine_diff_density_max 0.377 _refine_diff_density_min -0.293 _refine_diff_density_rms 0.067 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 O7 O 0.23681(9) 0.88391(15) 0.46272(6) 0.0422(3) Uani 1 1 d . . . O11 O -0.03254(9) 0.65537(17) 0.36150(6) 0.0473(3) Uani 1 1 d . . . O5 O 0.33090(9) 0.60566(16) 0.45734(6) 0.0444(3) Uani 1 1 d . . . O3 O 0.29170(10) 0.88141(16) 0.34861(6) 0.0458(3) Uani 1 1 d . . . O9 O 0.05202(10) 0.95942(17) 0.40418(7) 0.0507(4) Uani 1 1 d . . . C3 C 0.24735(13) 0.6372(2) 0.40230(8) 0.0376(4) Uani 1 1 d . . . H3 H 0.2133 0.5306 0.3883 0.045 Uiso 1 1 calc R . . O6 O 0.25158(13) 0.39224(19) 0.48582(8) 0.0626(4) Uani 1 1 d . . . O8 O 0.21221(14) 0.7722(2) 0.54946(7) 0.0684(5) Uani 1 1 d . . . C4 C 0.17784(12) 0.7545(2) 0.42366(8) 0.0377(4) Uani 1 1 d . . . H4 H 0.1445 0.69 0.4489 0.045 Uiso 1 1 calc R . . C5 C 0.10111(13) 0.8476(2) 0.37185(9) 0.0405(4) Uani 1 1 d . . . H5 H 0.1349 0.9152 0.3477 0.049 Uiso 1 1 calc R . . O10 O 0.10038(14) 1.1851(2) 0.36067(8) 0.0682(5) Uani 1 1 d . . . C13 C 0.32221(14) 0.4811(2) 0.49641(9) 0.0435(4) Uani 1 1 d . . . O1 O 0.39769(13) 0.6589(2) 0.26670(8) 0.0743(5) Uani 1 1 d . . . C6 C 0.02270(13) 0.7428(2) 0.32630(9) 0.0425(4) Uani 1 1 d . . . H6 H -0.0225 0.8201 0.2972 0.051 Uiso 1 1 calc R . . C2 C 0.29103(14) 0.7000(2) 0.35137(9) 0.0416(4) Uani 1 1 d . . . H2 H 0.3596 0.6621 0.3629 0.05 Uiso 1 1 calc R . . C16 C 0.24922(14) 0.8761(2) 0.52517(9) 0.0451(5) Uani 1 1 d . . . C18 C 0.06302(15) 1.1260(3) 0.39726(11) 0.0512(5) Uani 1 1 d . . . C7 C 0.05767(15) 0.6158(3) 0.28689(10) 0.0494(5) Uani 1 1 d . . . H7A H 0.0008 0.5729 0.2545 0.059 Uiso 1 1 calc R . . H7B H 0.0874 0.522 0.3138 0.059 Uiso 1 1 calc R . . C8 C 0.13135(16) 0.6816(3) 0.25497(9) 0.0526(5) Uani 1 1 d . . . H8A H 0.1266 0.8033 0.2535 0.063 Uiso 1 1 calc R . . H8B H 0.1114 0.6416 0.2117 0.063 Uiso 1 1 calc R . . C14 C 0.41056(17) 0.4726(3) 0.55267(10) 0.0637(6) Uani 1 1 d . . . H14A H 0.3973 0.5297 0.5874 0.096 Uiso 1 1 calc R . . H14B H 0.4651 0.5255 0.5431 0.096 Uiso 1 1 calc R . . H14C H 0.4263 0.357 0.5638 0.096 Uiso 1 1 calc R . . C9 C 0.29419(17) 0.6904(3) 0.23897(10) 0.0615(6) Uani 1 1 d . . . H9A H 0.27 0.6288 0.1996 0.074 Uiso 1 1 calc R . . H9B H 0.2831 0.8094 0.2299 0.074 Uiso 1 1 calc R . . C1 C 0.23980(15) 0.6345(3) 0.28490(9) 0.0469(5) Uani 1 1 d . . . H1 H 0.2433 0.5114 0.2869 0.056 Uiso 1 1 calc R . . C17 C 0.3153(2) 1.0119(3) 0.55884(11) 0.0697(7) Uani 1 1 d . . . H17A H 0.3181 1.0109 0.6027 0.105 Uiso 1 1 calc R . . H17B H 0.2905 1.1185 0.5406 0.105 Uiso 1 1 calc R . . H17C H 0.3801 0.9944 0.5551 0.105 Uiso 1 1 calc R . . O4 O 0.44833(16) 0.8928(3) 0.40695(16) 0.1296(11) Uani 1 1 d . . . C12 C 0.37409(18) 0.9634(3) 0.38015(14) 0.0682(7) Uani 1 1 d . . . C10 C 0.4582(2) 0.7188(4) 0.23727(12) 0.0695(7) Uani 1 1 d . . . C20 C -0.12879(16) 0.6808(3) 0.34619(12) 0.0611(6) Uani 1 1 d . . . O12 O -0.17104(15) 0.7734(4) 0.30510(14) 0.1396(13) Uani 1 1 d . . . O2 O 0.42971(19) 0.7804(4) 0.18670(11) 0.1237(10) Uani 1 1 d . . . C21 C -0.17545(19) 0.5805(4) 0.38551(13) 0.0713(7) Uani 1 1 d . . . H21A H -0.2202 0.6503 0.3993 0.107 Uiso 1 1 calc R . . H21B H -0.1256 0.5378 0.4216 0.107 Uiso 1 1 calc R . . H21C H -0.2109 0.4884 0.3611 0.107 Uiso 1 1 calc R . . C15 C 0.3571(3) 1.1481(3) 0.37842(19) 0.0919(10) Uani 1 1 d . . . H15A H 0.3254 1.178 0.4096 0.138 Uiso 1 1 calc R . . H15B H 0.3159 1.1799 0.3373 0.138 Uiso 1 1 calc R . . H15C H 0.419 1.2057 0.3873 0.138 Uiso 1 1 calc R . . C19 C 0.0221(2) 1.2234(3) 0.44101(15) 0.0805(8) Uani 1 1 d . . . H19A H 0.0333 1.3412 0.4367 0.121 Uiso 1 1 calc R . . H19B H 0.054 1.189 0.4837 0.121 Uiso 1 1 calc R . . H19C H -0.0473 1.2027 0.4309 0.121 Uiso 1 1 calc R . . C11 C 0.5633(2) 0.7023(6) 0.27475(16) 0.1066(12) Uani 1 1 d . . . H11A H 0.5805 0.5853 0.2803 0.16 Uiso 1 1 calc R . . H11B H 0.5736 0.7539 0.3153 0.16 Uiso 1 1 calc R . . H11C H 0.6038 0.7568 0.2529 0.16 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 O7 0.0395(7) 0.0452(7) 0.0431(7) -0.0015(5) 0.0142(5) -0.0081(5) O11 0.0321(7) 0.0524(8) 0.0560(8) 0.0111(6) 0.0111(6) -0.0008(6) O5 0.0336(6) 0.0521(8) 0.0447(7) 0.0097(6) 0.0072(5) 0.0007(5) O3 0.0414(7) 0.0463(8) 0.0540(8) 0.0063(6) 0.0207(6) -0.0006(6) O9 0.0405(7) 0.0483(8) 0.0691(9) -0.0018(7) 0.0250(7) 0.0040(6) C3 0.0311(8) 0.0420(10) 0.0374(9) 0.0039(7) 0.0065(7) 0.0023(7) O6 0.0635(10) 0.0583(9) 0.0613(9) 0.0154(7) 0.0112(8) -0.0114(8) O8 0.0818(12) 0.0765(11) 0.0511(9) 0.0019(8) 0.0260(8) -0.0240(9) C4 0.0314(8) 0.0408(9) 0.0420(10) 0.0003(7) 0.0127(7) -0.0045(7) C5 0.0343(9) 0.0399(10) 0.0505(10) 0.0022(8) 0.0175(8) 0.0025(7) O10 0.0827(12) 0.0508(9) 0.0703(10) 0.0069(8) 0.0216(9) 0.0005(8) C13 0.0450(10) 0.0458(10) 0.0412(10) 0.0052(8) 0.0150(8) 0.0065(9) O1 0.0570(10) 0.1093(14) 0.0681(10) 0.0291(10) 0.0362(8) 0.0251(9) C6 0.0308(8) 0.0471(10) 0.0479(10) 0.0094(8) 0.0091(8) 0.0012(7) C2 0.0356(9) 0.0469(10) 0.0445(10) 0.0046(8) 0.0152(8) 0.0047(7) C16 0.0405(10) 0.0478(11) 0.0454(10) 0.0005(8) 0.0104(8) 0.0026(8) C18 0.0337(9) 0.0490(12) 0.0628(13) -0.0043(10) 0.0020(9) 0.0060(8) C7 0.0400(10) 0.0567(12) 0.0463(11) -0.0034(9) 0.0051(8) -0.0030(9) C8 0.0489(11) 0.0657(13) 0.0416(10) -0.0008(9) 0.0109(9) 0.0045(10) C14 0.0542(13) 0.0813(16) 0.0504(12) 0.0159(11) 0.0075(10) 0.0082(12) C9 0.0550(13) 0.0870(17) 0.0468(12) 0.0050(11) 0.0218(10) 0.0113(12) C1 0.0472(11) 0.0536(11) 0.0418(10) 0.0011(8) 0.0163(8) 0.0068(9) C17 0.0812(17) 0.0619(14) 0.0542(13) -0.0030(11) 0.0020(12) -0.0152(12) O4 0.0471(11) 0.0954(16) 0.220(3) -0.0063(17) -0.0004(15) -0.0163(11) C12 0.0476(13) 0.0652(15) 0.0991(19) -0.0047(13) 0.0330(13) -0.0136(11) C10 0.0664(15) 0.0919(18) 0.0551(14) 0.0083(13) 0.0254(12) -0.0091(13) C20 0.0361(10) 0.0775(15) 0.0709(14) 0.0142(12) 0.0176(10) 0.0052(10) O12 0.0455(11) 0.209(3) 0.166(2) 0.121(2) 0.0341(13) 0.0346(14) O2 0.0823(15) 0.209(3) 0.0783(14) 0.0470(17) 0.0222(11) -0.0296(17) C21 0.0492(13) 0.0898(18) 0.0812(17) 0.0068(14) 0.0290(12) -0.0090(12) C15 0.094(2) 0.0616(16) 0.138(3) -0.0150(17) 0.061(2) -0.0262(15) C19 0.0668(16) 0.0682(16) 0.111(2) -0.0210(15) 0.0326(15) 0.0128(13) C11 0.0653(18) 0.165(3) 0.094(2) 0.026(2) 0.0318(17) 0.003(2) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 O7 C16 1.344(2) . ? O7 C4 1.442(2) . ? O11 C20 1.325(3) . ? O11 C6 1.440(2) . ? O5 C13 1.345(2) . ? O5 C3 1.450(2) . ? O3 C12 1.342(3) . ? O3 C2 1.444(2) . ? O9 C18 1.348(3) . ? O9 C5 1.445(2) . ? C3 C2 1.525(3) . ? C3 C4 1.533(2) . ? O6 C13 1.193(2) . ? O8 C16 1.191(2) . ? C4 C5 1.521(2) . ? C5 C6 1.513(3) . ? O10 C18 1.190(3) . ? C13 C14 1.486(3) . ? O1 C10 1.314(3) . ? O1 C9 1.439(3) . ? C6 C7 1.513(3) . ? C2 C1 1.528(3) . ? C16 C17 1.479(3) . ? C18 C19 1.488(3) . ? C7 C8 1.521(3) . ? C8 C1 1.534(3) . ? C9 C1 1.517(3) . ? O4 C12 1.188(3) . ? C12 C15 1.487(4) . ? C10 O2 1.179(3) . ? C10 C11 1.485(4) . ? C20 O12 1.186(3) . ? C20 C21 1.476(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 C16 O7 C4 117.40(14) . . ? C20 O11 C6 118.47(16) . . ? C13 O5 C3 117.38(14) . . ? C12 O3 C2 118.62(17) . . ? C18 O9 C5 117.29(16) . . ? O5 C3 C2 105.47(14) . . ? O5 C3 C4 106.77(14) . . ? C2 C3 C4 118.15(15) . . ? O7 C4 C5 105.36(14) . . ? O7 C4 C3 107.79(14) . . ? C5 C4 C3 116.57(15) . . ? O9 C5 C6 107.48(14) . . ? O9 C5 C4 105.63(14) . . ? C6 C5 C4 117.20(15) . . ? O6 C13 O5 122.84(18) . . ? O6 C13 C14 126.24(19) . . ? O5 C13 C14 110.91(18) . . ? C10 O1 C9 117.57(19) . . ? O11 C6 C7 108.47(16) . . ? O11 C6 C5 108.50(15) . . ? C7 C6 C5 116.68(15) . . ? O3 C2 C3 111.56(15) . . ? O3 C2 C1 107.88(15) . . ? C3 C2 C1 114.80(16) . . ? O8 C16 O7 123.86(18) . . ? O8 C16 C17 125.3(2) . . ? O7 C16 C17 110.81(18) . . ? O10 C18 O9 123.8(2) . . ? O10 C18 C19 125.4(2) . . ? O9 C18 C19 110.8(2) . . ? C6 C7 C8 115.43(18) . . ? C7 C8 C1 117.31(17) . . ? O1 C9 C1 108.90(17) . . ? C9 C1 C2 110.78(18) . . ? C9 C1 C8 106.66(16) . . ? C2 C1 C8 117.65(16) . . ? O4 C12 O3 122.7(2) . . ? O4 C12 C15 126.4(3) . . ? O3 C12 C15 110.9(2) . . ? O2 C10 O1 122.1(3) . . ? O2 C10 C11 124.9(3) . . ? O1 C10 C11 112.9(2) . . ? O12 C20 O11 122.7(2) . . ? O12 C20 C21 125.0(2) . . ? O11 C20 C21 112.2(2) . . ?