Supplementary Material (ESI) for Perkin Transactions This journal is © The Royal Society of Chemistry 2001 data_global _journal_coden_Cambridge 207 _publ_requested_journal 'Perkin Transactions 1' loop_ _publ_author_name 'Aburel, Pompiliu S.' 'Romming, Christian' 'Undheim, K.' _publ_contact_author_name 'Prof K Undheim' _publ_contact_author_address ; Prof K Undheim Department of Chemistry University of Oslo Pb 1033 Blinder Oslo N-0315 NORWAY ; data_7b _database_code_CSD 156270 _audit_creation_method SHELXL _chemical_name_systematic ; trans.7,7-Ethylenedioxybicyclo(4.4.0)decan-3-one ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C12 H18 O3' _chemical_formula_weight 210.26 _chemical_melting_point ? _chemical_compound_source ? 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 ? _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.60230(10) _cell_length_b 9.0705(2) _cell_length_c 11.2383(3) _cell_angle_alpha 100.2030(10) _cell_angle_beta 99.7840(10) _cell_angle_gamma 99.3230(10) _cell_volume 542.90(2) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.8 _exptl_crystal_size_mid 0.6 _exptl_crystal_size_min 0.5 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.286 _exptl_crystal_density_method ? _exptl_crystal_F_000 228 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 ? _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9220 _diffrn_reflns_av_R_equivalents 0.0119 _diffrn_reflns_av_sigmaI/netI 0.0168 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.33 _diffrn_reflns_theta_max 36.14 _reflns_number_total 4640 _reflns_number_observed 4219 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0610P)^2^+0.0700P] 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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4640 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0434 _refine_ls_R_factor_obs 0.0389 _refine_ls_wR_factor_all 0.1168 _refine_ls_wR_factor_obs 0.1115 _refine_ls_goodness_of_fit_all 1.118 _refine_ls_goodness_of_fit_obs 1.122 _refine_ls_restrained_S_all 1.118 _refine_ls_restrained_S_obs 1.122 _refine_ls_shift/esd_max -0.004 _refine_ls_shift/esd_mean 0.001 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O1 O 0.13289(9) 0.44157(5) 0.64750(4) 0.02014(10) Uani 1 d . . O2 O 0.48567(10) 0.55397(6) 0.79386(5) 0.02553(11) Uani 1 d . . O3 O -0.28072(11) 0.03834(7) 0.90460(6) 0.03127(13) Uani 1 d . . C1 C 0.35287(11) 0.41070(7) 0.71854(6) 0.01796(10) Uani 1 d . . C2 C 0.4113(2) 0.67064(8) 0.73273(8) 0.0316(2) Uani 1 d . . H2A H 0.4426(25) 0.7629(16) 0.7939(13) 0.043(3) Uiso 1 d . . H2B H 0.5120(26) 0.6859(15) 0.6681(13) 0.039(3) Uiso 1 d . . C3 C 0.1410(2) 0.60349(8) 0.67473(7) 0.02798(14) Uani 1 d . . H3A H 0.0307(25) 0.6256(15) 0.7311(13) 0.040(3) Uiso 1 d . . H3B H 0.0808(25) 0.6352(15) 0.5990(13) 0.038(3) Uiso 1 d . . C4 C 0.50417(12) 0.34375(8) 0.62841(7) 0.02396(12) Uani 1 d . . H4A H 0.6576(24) 0.3310(15) 0.6751(12) 0.034(3) Uiso 1 d . . H4B H 0.5430(24) 0.4197(15) 0.5761(12) 0.037(3) Uiso 1 d . . C5 C 0.36423(14) 0.18788(8) 0.54932(6) 0.02461(13) Uani 1 d . . H5A H 0.2141(21) 0.2024(13) 0.4971(11) 0.025(2) Uiso 1 d . . H5B H 0.4696(26) 0.1424(16) 0.4932(13) 0.042(3) Uiso 1 d . . C6 C 0.28956(13) 0.07714(7) 0.63152(6) 0.02221(12) Uani 1 d . . H6A H 0.4368(23) 0.0506(14) 0.6793(12) 0.031(3) Uiso 1 d . . H6B H 0.1953(24) -0.0214(15) 0.5801(12) 0.036(3) Uiso 1 d . . C7 C 0.13871(11) 0.14481(6) 0.72203(5) 0.01688(10) Uani 1 d . . H7 H -0.0107(20) 0.1630(12) 0.6748(10) 0.022(2) Uiso 1 d . . C8 C 0.06547(13) 0.03180(7) 0.80400(6) 0.02180(12) Uani 1 d . . H8A H 0.2118(23) 0.0064(14) 0.8494(11) 0.032(3) Uiso 1 d . . H8B H -0.0391(25) -0.0672(15) 0.7525(13) 0.040(3) Uiso 1 d . . C9 C -0.07532(12) 0.10070(7) 0.89631(6) 0.02072(11) Uani 1 d . . C10 C 0.0562(2) 0.25431(8) 0.97585(6) 0.02561(13) Uani 1 d . . H10A H 0.2019(25) 0.2406(15) 1.0276(13) 0.037(3) Uiso 1 d . . H10B H -0.0556(27) 0.2937(17) 1.0306(14) 0.048(4) Uiso 1 d . . C11 C 0.13614(13) 0.36813(7) 0.89598(6) 0.02082(11) Uani 1 d . . H11A H -0.0090(21) 0.3979(13) 0.8512(10) 0.025(2) Uiso 1 d . . H11B H 0.2331(25) 0.4613(15) 0.9519(12) 0.036(3) Uiso 1 d . . C12 C 0.28253(11) 0.30085(6) 0.80266(5) 0.01693(10) Uani 1 d . . H12 H 0.4429(22) 0.2825(14) 0.8492(11) 0.027(3) Uiso 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 0.0196(2) 0.0172(2) 0.0219(2) 0.00418(15) -0.00198(15) 0.00495(15) O2 0.0263(2) 0.0172(2) 0.0262(2) 0.0045(2) -0.0059(2) -0.0036(2) O3 0.0274(3) 0.0327(3) 0.0343(3) 0.0106(2) 0.0084(2) 0.0018(2) C1 0.0155(2) 0.0164(2) 0.0197(2) 0.0038(2) -0.0010(2) 0.0014(2) C2 0.0407(4) 0.0174(3) 0.0314(3) 0.0073(2) -0.0030(3) -0.0012(2) C3 0.0358(4) 0.0185(3) 0.0278(3) 0.0043(2) -0.0019(3) 0.0096(2) C4 0.0185(3) 0.0266(3) 0.0288(3) 0.0087(2) 0.0070(2) 0.0050(2) C5 0.0278(3) 0.0254(3) 0.0235(3) 0.0042(2) 0.0101(2) 0.0096(2) C6 0.0256(3) 0.0191(2) 0.0232(3) 0.0020(2) 0.0068(2) 0.0087(2) C7 0.0183(2) 0.0143(2) 0.0172(2) 0.0015(2) 0.0021(2) 0.0042(2) C8 0.0273(3) 0.0148(2) 0.0229(3) 0.0035(2) 0.0052(2) 0.0035(2) C9 0.0250(3) 0.0192(2) 0.0185(2) 0.0068(2) 0.0031(2) 0.0041(2) C10 0.0368(4) 0.0213(3) 0.0174(2) 0.0020(2) 0.0063(2) 0.0033(2) C11 0.0277(3) 0.0156(2) 0.0181(2) 0.0012(2) 0.0040(2) 0.0046(2) C12 0.0173(2) 0.0147(2) 0.0171(2) 0.0026(2) -0.0001(2) 0.0031(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C3 1.4378(8) . ? O1 C1 1.4461(7) . ? O2 C1 1.4289(8) . ? O2 C2 1.4384(9) . ? O3 C9 1.2236(9) . ? C1 C4 1.5343(9) . ? C1 C12 1.5411(8) . ? C2 C3 1.5211(12) . ? C2 H2A 0.955(14) . ? C2 H2B 1.007(14) . ? C3 H3A 0.975(14) . ? C3 H3B 0.970(13) . ? C4 C5 1.5370(10) . ? C4 H4A 0.963(13) . ? C4 H4B 1.003(13) . ? C5 C6 1.5366(10) . ? C5 H5A 0.983(12) . ? C5 H5B 1.015(14) . ? C6 C7 1.5378(8) . ? C6 H6A 0.993(12) . ? C6 H6B 0.986(13) . ? C7 C8 1.5474(9) . ? C7 C12 1.5496(8) . ? C7 H7 0.966(11) . ? C8 C9 1.5156(9) . ? C8 H8A 0.973(13) . ? C8 H8B 1.007(14) . ? C9 C10 1.5117(9) . ? C10 C11 1.5451(9) . ? C10 H10A 0.958(14) . ? C10 H10B 1.012(15) . ? C11 C12 1.5404(9) . ? C11 H11A 0.983(11) . ? C11 H11B 0.976(13) . ? C12 H12 1.014(12) . ? 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 C3 O1 C1 108.65(5) . . ? C1 O2 C2 106.69(5) . . ? O2 C1 O1 106.39(5) . . ? O2 C1 C4 111.15(5) . . ? O1 C1 C4 108.35(5) . . ? O2 C1 C12 108.97(5) . . ? O1 C1 C12 110.28(5) . . ? C4 C1 C12 111.58(5) . . ? O2 C2 C3 102.61(6) . . ? O2 C2 H2A 107.3(8) . . ? C3 C2 H2A 115.9(8) . . ? O2 C2 H2B 109.8(8) . . ? C3 C2 H2B 111.5(8) . . ? H2A C2 H2B 109.4(11) . . ? O1 C3 C2 103.53(6) . . ? O1 C3 H3A 109.0(8) . . ? C2 C3 H3A 112.8(8) . . ? O1 C3 H3B 109.0(8) . . ? C2 C3 H3B 114.5(8) . . ? H3A C3 H3B 107.7(11) . . ? C1 C4 C5 111.26(5) . . ? C1 C4 H4A 108.8(8) . . ? C5 C4 H4A 109.0(8) . . ? C1 C4 H4B 107.8(8) . . ? C5 C4 H4B 111.6(8) . . ? H4A C4 H4B 108.2(11) . . ? C6 C5 C4 110.75(6) . . ? C6 C5 H5A 108.8(7) . . ? C4 C5 H5A 108.8(7) . . ? C6 C5 H5B 109.9(8) . . ? C4 C5 H5B 110.5(8) . . ? H5A C5 H5B 108.1(10) . . ? C5 C6 C7 111.51(5) . . ? C5 C6 H6A 111.3(7) . . ? C7 C6 H6A 108.9(7) . . ? C5 C6 H6B 110.2(8) . . ? C7 C6 H6B 110.4(8) . . ? H6A C6 H6B 104.4(10) . . ? C6 C7 C8 110.74(5) . . ? C6 C7 C12 111.17(5) . . ? C8 C7 C12 110.71(5) . . ? C6 C7 H7 108.5(6) . . ? C8 C7 H7 108.4(7) . . ? C12 C7 H7 107.2(6) . . ? C9 C8 C7 110.76(5) . . ? C9 C8 H8A 108.4(7) . . ? C7 C8 H8A 110.5(7) . . ? C9 C8 H8B 109.1(8) . . ? C7 C8 H8B 111.2(8) . . ? H8A C8 H8B 106.8(10) . . ? O3 C9 C10 122.56(6) . . ? O3 C9 C8 122.78(6) . . ? C10 C9 C8 114.65(6) . . ? C9 C10 C11 111.19(5) . . ? C9 C10 H10A 108.4(8) . . ? C11 C10 H10A 108.0(8) . . ? C9 C10 H10B 108.9(9) . . ? C11 C10 H10B 111.9(8) . . ? H10A C10 H10B 108.3(12) . . ? C12 C11 C10 111.84(5) . . ? C12 C11 H11A 109.2(6) . . ? C10 C11 H11A 110.5(7) . . ? C12 C11 H11B 111.6(8) . . ? C10 C11 H11B 107.5(8) . . ? H11A C11 H11B 106.0(10) . . ? C11 C12 C1 112.23(5) . . ? C11 C12 C7 111.72(5) . . ? C1 C12 C7 109.49(5) . . ? C11 C12 H12 109.2(7) . . ? C1 C12 H12 106.8(7) . . ? C7 C12 H12 107.2(7) . . ? 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 C2 O2 C1 O1 -24.42(7) . . . . ? C2 O2 C1 C4 93.33(7) . . . . ? C2 O2 C1 C12 -143.31(6) . . . . ? C3 O1 C1 O2 3.31(7) . . . . ? C3 O1 C1 C4 -116.28(6) . . . . ? C3 O1 C1 C12 121.33(6) . . . . ? C1 O2 C2 C3 34.61(8) . . . . ? C1 O1 C3 C2 17.57(7) . . . . ? O2 C2 C3 O1 -31.64(8) . . . . ? O2 C1 C4 C5 178.69(5) . . . . ? O1 C1 C4 C5 -64.76(6) . . . . ? C12 C1 C4 C5 56.84(7) . . . . ? C1 C4 C5 C6 -55.21(7) . . . . ? C4 C5 C6 C7 55.23(7) . . . . ? C5 C6 C7 C8 -179.96(5) . . . . ? C5 C6 C7 C12 -56.44(7) . . . . ? C6 C7 C8 C9 177.97(5) . . . . ? C12 C7 C8 C9 54.19(7) . . . . ? C7 C8 C9 O3 124.44(7) . . . . ? C7 C8 C9 C10 -54.45(7) . . . . ? O3 C9 C10 C11 -125.92(7) . . . . ? C8 C9 C10 C11 52.97(8) . . . . ? C9 C10 C11 C12 -51.78(8) . . . . ? C10 C11 C12 C1 177.39(5) . . . . ? C10 C11 C12 C7 53.97(7) . . . . ? O2 C1 C12 C11 55.44(6) . . . . ? O1 C1 C12 C11 -60.99(6) . . . . ? C4 C1 C12 C11 178.55(5) . . . . ? O2 C1 C12 C7 -179.90(5) . . . . ? O1 C1 C12 C7 63.67(6) . . . . ? C4 C1 C12 C7 -56.79(6) . . . . ? C6 C7 C12 C11 -178.61(5) . . . . ? C8 C7 C12 C11 -55.07(6) . . . . ? C6 C7 C12 C1 56.44(6) . . . . ? C8 C7 C12 C1 179.97(5) . . . . ? _refine_diff_density_max 0.484 _refine_diff_density_min -0.184 _refine_diff_density_rms 0.046 #=END data_10 _database_code_CSD 156271 _audit_creation_method SHELXL-97 _chemical_name_systematic ; trans-7,7-(ethylenedioxy)bicyclo(4.4.0)dec-3-yl p-nitrobenzoate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H25 N O6' _chemical_formula_weight 375.41 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 ? _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 5.4613(9) _cell_length_b 16.035(3) _cell_length_c 20.772(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1819.1(5) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.7 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.371 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19667 _diffrn_reflns_av_R_equivalents 0.0818 _diffrn_reflns_av_sigmaI/netI 0.0449 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.60 _diffrn_reflns_theta_max 24.71 _reflns_number_total 3109 _reflns_number_gt 2457 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0657P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 1.5(14) _refine_ls_number_reflns 3109 _refine_ls_number_parameters 344 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0548 _refine_ls_R_factor_gt 0.0379 _refine_ls_wR_factor_ref 0.1053 _refine_ls_wR_factor_gt 0.0873 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _refine_ls_shift/su_max 0.004 _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 0.2994(3) 0.70047(11) 0.42805(8) 0.0294(4) Uani 1 1 d . . . O2 O -0.0526(3) 0.71095(11) 0.36917(9) 0.0294(4) Uani 1 1 d . . . O3 O 0.6309(3) 0.66123(11) 0.13562(8) 0.0321(4) Uani 1 1 d . . . O4 O 0.4797(4) 0.53566(12) 0.10664(10) 0.0415(5) Uani 1 1 d . . . O5 O 1.3241(6) 0.54344(14) -0.14226(11) 0.0674(8) Uani 1 1 d . . . O6 O 1.4900(4) 0.65194(14) -0.10119(11) 0.0589(7) Uani 1 1 d . . . N1 N 1.3359(5) 0.59729(15) -0.10107(12) 0.0415(6) Uani 1 1 d . . . C1 C 0.1063(5) 0.6660(2) 0.46605(14) 0.0317(6) Uani 1 1 d . . . H1A H 0.181(5) 0.6166(17) 0.4877(12) 0.029(7) Uiso 1 1 d . . . H1B H 0.052(6) 0.7021(19) 0.4947(15) 0.039(8) Uiso 1 1 d . . . C2 C -0.0875(5) 0.64752(18) 0.41620(14) 0.0336(7) Uani 1 1 d . . . H2A H -0.254(6) 0.6513(18) 0.4284(14) 0.042(8) Uiso 1 1 d . . . H2B H -0.058(6) 0.595(2) 0.3919(14) 0.044(8) Uiso 1 1 d . . . C3 C 0.1845(5) 0.74709(15) 0.37707(11) 0.0255(6) Uani 1 1 d . . . C4 C 0.1538(6) 0.83736(17) 0.39914(13) 0.0302(6) Uani 1 1 d . . . H4A H 0.310(5) 0.8653(16) 0.3952(12) 0.023(6) Uiso 1 1 d . . . H4B H 0.092(5) 0.8311(17) 0.4410(15) 0.033(7) Uiso 1 1 d . . . C5 C -0.0356(6) 0.88813(18) 0.36229(15) 0.0367(7) Uani 1 1 d . . . H5A H -0.105(6) 0.934(2) 0.3848(16) 0.050(9) Uiso 1 1 d . . . H5B H -0.178(6) 0.853(2) 0.3532(14) 0.047(9) Uiso 1 1 d . . . C6 C 0.0433(7) 0.9189(2) 0.29637(16) 0.0433(8) Uani 1 1 d . . . H6A H -0.086(7) 0.913(2) 0.2670(17) 0.054(10) Uiso 1 1 d . . . H6B H 0.077(8) 0.980(3) 0.297(2) 0.097(15) Uiso 1 1 d . . . C7 C 0.2694(6) 0.87958(16) 0.26644(14) 0.0322(6) Uani 1 1 d . . . H7A H 0.414(5) 0.8917(17) 0.2900(13) 0.027(7) Uiso 1 1 d . . . H7B H 0.287(5) 0.9060(18) 0.2258(14) 0.036(8) Uiso 1 1 d . . . C8 C 0.2640(5) 0.78410(15) 0.25737(12) 0.0257(6) Uani 1 1 d . . . H8 H 0.101(5) 0.7684(15) 0.2469(12) 0.025(7) Uiso 1 1 d . . . C9 C 0.3415(5) 0.73373(15) 0.31709(12) 0.0246(6) Uani 1 1 d . . . H9 H 0.515(5) 0.7504(13) 0.3277(11) 0.011(5) Uiso 1 1 d . . . C10 C 0.3545(6) 0.64056(16) 0.30084(13) 0.0294(6) Uani 1 1 d . . . H10A H 0.176(6) 0.6214(17) 0.2873(14) 0.037(8) Uiso 1 1 d . . . H10B H 0.403(5) 0.6102(16) 0.3345(13) 0.026(7) Uiso 1 1 d . . . C11 C 0.5312(6) 0.62184(17) 0.24668(13) 0.0305(6) Uani 1 1 d . . . H11A H 0.693(6) 0.6380(16) 0.2576(12) 0.029(7) Uiso 1 1 d . . . H11B H 0.552(5) 0.5634(18) 0.2405(13) 0.032(7) Uiso 1 1 d . . . C12 C 0.4518(5) 0.66982(16) 0.18755(12) 0.0290(6) Uani 1 1 d . . . H12 H 0.294(5) 0.6479(15) 0.1741(11) 0.021(6) Uiso 1 1 d . . . C13 C 0.4361(6) 0.76265(16) 0.20153(13) 0.0290(6) Uani 1 1 d . . . H13A H 0.606(6) 0.7804(16) 0.2119(13) 0.031(7) Uiso 1 1 d . . . H13B H 0.373(5) 0.7918(17) 0.1665(14) 0.032(7) Uiso 1 1 d . . . C14 C 0.6246(5) 0.59164(16) 0.10000(12) 0.0291(6) Uani 1 1 d . . . C15 C 0.8176(5) 0.59354(15) 0.04907(12) 0.0282(6) Uani 1 1 d . . . C16 C 0.8135(6) 0.53239(18) 0.00184(14) 0.0392(7) Uani 1 1 d . . . H16 H 0.678(6) 0.492(2) 0.0046(14) 0.044(8) Uiso 1 1 d . . . C17 C 0.9842(6) 0.53279(18) -0.04745(14) 0.0407(8) Uani 1 1 d . . . H17 H 0.984(6) 0.489(2) -0.0849(14) 0.048(9) Uiso 1 1 d . . . C18 C 1.1565(5) 0.59522(16) -0.04832(13) 0.0320(6) Uani 1 1 d . . . C19 C 1.1680(5) 0.65603(17) -0.00148(13) 0.0339(6) Uani 1 1 d . . . H19 H 1.296(5) 0.6998(15) -0.0053(12) 0.022(6) Uiso 1 1 d . . . C20 C 0.9963(5) 0.65475(17) 0.04735(13) 0.0305(6) Uani 1 1 d . . . H20 H 0.997(6) 0.6981(19) 0.0833(15) 0.044(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 0.0281(9) 0.0409(10) 0.0191(8) 0.0060(8) -0.0002(8) 0.0023(8) O2 0.0229(9) 0.0370(9) 0.0284(9) 0.0054(8) -0.0025(8) -0.0019(8) O3 0.0388(11) 0.0349(10) 0.0227(9) -0.0060(8) 0.0074(8) -0.0026(9) O4 0.0469(12) 0.0394(11) 0.0380(11) -0.0071(9) 0.0109(10) -0.0121(11) O5 0.103(2) 0.0499(14) 0.0493(14) -0.0171(12) 0.0416(15) -0.0165(14) O6 0.0621(15) 0.0449(13) 0.0697(15) -0.0093(11) 0.0397(13) -0.0100(13) N1 0.0543(17) 0.0295(12) 0.0407(14) 0.0015(12) 0.0203(13) 0.0045(12) C1 0.0309(16) 0.0365(15) 0.0276(15) 0.0047(14) 0.0100(12) 0.0042(13) C2 0.0298(16) 0.0382(16) 0.0328(15) 0.0049(13) 0.0076(13) -0.0025(13) C3 0.0213(13) 0.0347(13) 0.0205(13) 0.0018(11) -0.0016(11) 0.0011(11) C4 0.0350(17) 0.0342(15) 0.0215(14) -0.0019(12) 0.0027(13) 0.0008(14) C5 0.0343(17) 0.0351(15) 0.0406(17) -0.0015(14) 0.0060(15) 0.0060(14) C6 0.0463(19) 0.051(2) 0.0320(17) 0.0043(15) 0.0014(16) 0.0173(16) C7 0.0374(17) 0.0311(14) 0.0281(15) 0.0050(13) 0.0026(14) 0.0013(12) C8 0.0248(15) 0.0313(13) 0.0209(13) 0.0021(11) -0.0015(11) -0.0019(11) C9 0.0226(15) 0.0285(13) 0.0227(13) 0.0004(10) -0.0006(11) -0.0002(11) C10 0.0384(16) 0.0276(13) 0.0222(13) 0.0044(12) -0.0005(13) 0.0022(12) C11 0.0364(18) 0.0284(15) 0.0269(14) -0.0003(12) 0.0009(13) 0.0055(12) C12 0.0298(15) 0.0340(14) 0.0232(14) -0.0013(12) 0.0030(12) -0.0031(12) C13 0.0334(17) 0.0309(13) 0.0228(14) 0.0047(12) 0.0016(13) 0.0009(12) C14 0.0339(16) 0.0295(14) 0.0240(14) -0.0001(11) -0.0029(12) 0.0011(13) C15 0.0344(15) 0.0278(13) 0.0224(13) 0.0012(11) -0.0032(12) 0.0020(12) C16 0.0496(18) 0.0346(15) 0.0333(16) -0.0071(13) 0.0073(15) -0.0095(15) C17 0.056(2) 0.0345(15) 0.0316(16) -0.0061(13) 0.0102(16) -0.0039(15) C18 0.0413(16) 0.0278(13) 0.0269(14) 0.0032(11) 0.0070(13) 0.0030(12) C19 0.0381(16) 0.0282(14) 0.0352(15) 0.0013(12) 0.0048(14) -0.0010(14) C20 0.0341(15) 0.0296(14) 0.0279(14) -0.0031(12) 0.0010(13) 0.0019(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.429(3) . ? O1 C3 1.440(3) . ? O2 C2 1.423(3) . ? O2 C3 1.428(3) . ? O3 C14 1.339(3) . ? O3 C12 1.463(3) . ? O4 C14 1.204(3) . ? O5 N1 1.217(3) . ? O6 N1 1.215(3) . ? N1 C18 1.470(3) . ? C1 C2 1.510(4) . ? C1 H1A 1.00(3) . ? C1 H1B 0.88(3) . ? C2 H2A 0.94(3) . ? C2 H2B 0.99(3) . ? C3 C4 1.527(4) . ? C3 C9 1.528(4) . ? C4 C5 1.523(4) . ? C4 H4A 0.97(3) . ? C4 H4B 0.94(3) . ? C5 C6 1.518(4) . ? C5 H5A 0.95(3) . ? C5 H5B 0.98(4) . ? C6 C7 1.520(4) . ? C6 H6A 0.94(4) . ? C6 H6B 1.00(5) . ? C7 C8 1.543(4) . ? C7 H7A 0.95(3) . ? C7 H7B 0.95(3) . ? C8 C13 1.532(4) . ? C8 C9 1.540(3) . ? C8 H8 0.95(3) . ? C9 C10 1.533(4) . ? C9 H9 1.01(3) . ? C10 C11 1.512(4) . ? C10 H10A 1.06(3) . ? C10 H10B 0.89(3) . ? C11 C12 1.513(4) . ? C11 H11A 0.95(3) . ? C11 H11B 0.95(3) . ? C12 C13 1.519(4) . ? C12 H12 0.97(3) . ? C13 H13A 0.99(3) . ? C13 H13B 0.93(3) . ? C14 C15 1.494(4) . ? C15 C20 1.385(4) . ? C15 C16 1.387(4) . ? C16 C17 1.385(4) . ? C16 H16 0.98(4) . ? C17 C18 1.374(4) . ? C17 H17 1.05(3) . ? C18 C19 1.379(4) . ? C19 C20 1.381(4) . ? C19 H19 0.99(3) . ? C20 H20 1.02(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 C3 106.58(19) . . ? C2 O2 C3 109.43(19) . . ? C14 O3 C12 117.9(2) . . ? O6 N1 O5 123.2(2) . . ? O6 N1 C18 118.6(2) . . ? O5 N1 C18 118.2(3) . . ? O1 C1 C2 102.4(2) . . ? O1 C1 H1A 104.7(16) . . ? C2 C1 H1A 116.1(15) . . ? O1 C1 H1B 112(2) . . ? C2 C1 H1B 111(2) . . ? H1A C1 H1B 111(2) . . ? O2 C2 C1 103.7(2) . . ? O2 C2 H2A 105.5(18) . . ? C1 C2 H2A 118.5(18) . . ? O2 C2 H2B 103.6(17) . . ? C1 C2 H2B 113.5(18) . . ? H2A C2 H2B 110(3) . . ? O2 C3 O1 105.60(19) . . ? O2 C3 C4 108.6(2) . . ? O1 C3 C4 108.61(19) . . ? O2 C3 C9 110.98(19) . . ? O1 C3 C9 106.40(19) . . ? C4 C3 C9 116.1(2) . . ? C5 C4 C3 115.5(2) . . ? C5 C4 H4A 108.0(15) . . ? C3 C4 H4A 108.5(15) . . ? C5 C4 H4B 106.2(17) . . ? C3 C4 H4B 102.5(17) . . ? H4A C4 H4B 116(2) . . ? C6 C5 C4 115.8(3) . . ? C6 C5 H5A 107.6(19) . . ? C4 C5 H5A 116(2) . . ? C6 C5 H5B 103.8(18) . . ? C4 C5 H5B 109.3(18) . . ? H5A C5 H5B 103(3) . . ? C5 C6 C7 117.7(3) . . ? C5 C6 H6A 110(2) . . ? C7 C6 H6A 108(2) . . ? C5 C6 H6B 111(3) . . ? C7 C6 H6B 105(3) . . ? H6A C6 H6B 104(3) . . ? C6 C7 C8 116.5(3) . . ? C6 C7 H7A 112.3(16) . . ? C8 C7 H7A 106.4(16) . . ? C6 C7 H7B 105.2(18) . . ? C8 C7 H7B 109.6(17) . . ? H7A C7 H7B 106(3) . . ? C13 C8 C9 108.9(2) . . ? C13 C8 C7 107.7(2) . . ? C9 C8 C7 114.6(2) . . ? C13 C8 H8 110.0(16) . . ? C9 C8 H8 107.6(16) . . ? C7 C8 H8 108.0(15) . . ? C3 C9 C10 110.0(2) . . ? C3 C9 C8 115.4(2) . . ? C10 C9 C8 110.3(2) . . ? C3 C9 H9 108.2(13) . . ? C10 C9 H9 105.3(12) . . ? C8 C9 H9 107.1(13) . . ? C11 C10 C9 112.8(2) . . ? C11 C10 H10A 109.3(15) . . ? C9 C10 H10A 107.4(15) . . ? C11 C10 H10B 106.7(17) . . ? C9 C10 H10B 111.9(17) . . ? H10A C10 H10B 109(2) . . ? C10 C11 C12 108.7(2) . . ? C10 C11 H11A 111.3(16) . . ? C12 C11 H11A 108.8(16) . . ? C10 C11 H11B 111.7(17) . . ? C12 C11 H11B 115.1(16) . . ? H11A C11 H11B 101(2) . . ? O3 C12 C11 111.0(2) . . ? O3 C12 C13 105.7(2) . . ? C11 C12 C13 111.0(2) . . ? O3 C12 H12 110.3(14) . . ? C11 C12 H12 107.7(15) . . ? C13 C12 H12 111.1(15) . . ? C12 C13 C8 113.5(2) . . ? C12 C13 H13A 105.7(15) . . ? C8 C13 H13A 110.2(16) . . ? C12 C13 H13B 111.3(17) . . ? C8 C13 H13B 104.7(17) . . ? H13A C13 H13B 112(2) . . ? O4 C14 O3 125.1(2) . . ? O4 C14 C15 124.0(2) . . ? O3 C14 C15 110.9(2) . . ? C20 C15 C16 119.6(3) . . ? C20 C15 C14 122.0(2) . . ? C16 C15 C14 118.4(2) . . ? C17 C16 C15 120.6(3) . . ? C17 C16 H16 123.6(18) . . ? C15 C16 H16 115.7(18) . . ? C18 C17 C16 118.3(3) . . ? C18 C17 H17 118.7(18) . . ? C16 C17 H17 123.0(18) . . ? C17 C18 C19 122.5(3) . . ? C17 C18 N1 118.9(2) . . ? C19 C18 N1 118.7(2) . . ? C18 C19 C20 118.5(3) . . ? C18 C19 H19 118.4(14) . . ? C20 C19 H19 123.1(14) . . ? C19 C20 C15 120.5(3) . . ? C19 C20 H20 121.7(17) . . ? C15 C20 H20 117.8(17) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.71 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.151 _refine_diff_density_min -0.213 _refine_diff_density_rms 0.043