# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2003 data_global _journal_coden_Cambridge 177 _publ_contact_author_name 'Prof J.C. Anderson' _publ_contact_author_address ; School of Chemistry University of Nottingham University Park Nottingham NG7 2RD ; _publ_contact_author_email J.ANDERSON@NOTTINGHAM.AC.UK _publ_requested_journal 'Organic & Biomolecular Chemistry' _publ_section_title ; Investigation of the Asymmetric Ionic Diels-Alder Reaction for the Synthesis of cis-Decalins ; loop_ _publ_author_name 'J. C. Anderson' 'A.J. Blake' 'J.P. Graham' 'C. Wilson' data_compound8 _database_code_CSD 210314 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H26 O2' _chemical_formula_sum 'C16 H26 O2' _chemical_formula_weight 250.37 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 Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' 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 6.8589(11) _cell_length_b 10.727(2) _cell_length_c 20.398(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1500.7(7) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4714 _cell_measurement_theta_min 2.75 _cell_measurement_theta_max 28.75 _exptl_crystal_description 'trigonal prism' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.80 _exptl_crystal_size_mid 0.55 _exptl_crystal_size_min 0.29 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.108 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 0.071 _exptl_absorpt_correction_type none _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 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART1000 CCD area detector' _diffrn_measurement_method omega _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 9187 _diffrn_reflns_av_R_equivalents 0.081 _diffrn_reflns_av_sigmaI/netI 0.018 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.00 _diffrn_reflns_theta_max 28.75 _reflns_number_total 2067 _reflns_number_gt 1787 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART version 5.624 (Bruker, 2001)' _computing_cell_refinement 'Bruker SAINT version 6.02a (Bruker, 2000)' _computing_data_reduction 'Bruker SAINT; Bruker SHELXTL (Bruker, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'SHELXL-97; PLATON (Spek, 2002)' _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^)+(0.087P)^2^+0.018P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary 'direct methods' _atom_sites_solution_secondary . _atom_sites_solution_hydrogens 'sp2 Me groups from delta-F; others placed geometrically' _refine_ls_hydrogen_treatment 'rigid rotating group; riding model' _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 'not reliably determined' _refine_ls_number_reflns 2045 _refine_ls_number_parameters 165 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0485 _refine_ls_R_factor_gt 0.0423 _refine_ls_wR_factor_ref 0.120 _refine_ls_wR_factor_gt 0.115 _refine_ls_goodness_of_fit_ref 1.06 _refine_ls_restrained_S_all 1.06 _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 0.4727(3) 0.26286(18) 0.14432(8) 0.0369(4) Uani 1 1 d . . . C2 C 0.5270(4) 0.39844(19) 0.13254(10) 0.0512(5) Uani 1 1 d . . . H2A H 0.4379 0.4525 0.1580 0.061 Uiso 1 1 calc R . . H2B H 0.5087 0.4181 0.0855 0.061 Uiso 1 1 calc R . . C3 C 0.7371(4) 0.4278(2) 0.15190(11) 0.0545(6) Uani 1 1 d . . . H3A H 0.7605 0.5184 0.1474 0.065 Uiso 1 1 calc R . . H3B H 0.8273 0.3838 0.1219 0.065 Uiso 1 1 calc R . . C4 C 0.7794(3) 0.38772(18) 0.22288(9) 0.0429(4) Uani 1 1 d . . . H4A H 0.9183 0.4033 0.2333 0.051 Uiso 1 1 calc R . . H4B H 0.6987 0.4374 0.2534 0.051 Uiso 1 1 calc R . . C5 C 0.7336(3) 0.24859(16) 0.23152(8) 0.0339(4) Uani 1 1 d . . . H5A H 0.8168 0.2014 0.1998 0.041 Uiso 1 1 calc R . . C6 C 0.7811(2) 0.2002(2) 0.30042(9) 0.0407(4) Uani 1 1 d . . . H6A H 0.7982 0.1087 0.2982 0.049 Uiso 1 1 calc R . . H6B H 0.9068 0.2367 0.3146 0.049 Uiso 1 1 calc R . . C7 C 0.6275(3) 0.22967(18) 0.35180(8) 0.0354(4) Uani 1 1 d . . . C7M C 0.6988(3) 0.2105(2) 0.42150(10) 0.0489(5) Uani 1 1 d . . . H7MA H 0.7821 0.2806 0.4343 0.073 Uiso 1 1 calc R . . H7MB H 0.7736 0.1328 0.4240 0.073 Uiso 1 1 calc R . . H7MC H 0.5867 0.2057 0.4512 0.073 Uiso 1 1 calc R . . C8 C 0.4468(2) 0.26484(17) 0.33593(8) 0.0337(4) Uani 1 1 d . . . C8M C 0.2900(3) 0.2973(2) 0.38516(9) 0.0430(5) Uani 1 1 d . . . H8MA H 0.1872 0.2339 0.3838 0.064 Uiso 1 1 calc R . . H8MB H 0.2345 0.3789 0.3744 0.064 Uiso 1 1 calc R . . H8MC H 0.3468 0.3000 0.4292 0.064 Uiso 1 1 calc R . . C9 C 0.3795(2) 0.27761(18) 0.26507(8) 0.0350(4) Uani 1 1 d . . . H9A H 0.3628 0.3672 0.2549 0.042 Uiso 1 1 calc R . . H9B H 0.2504 0.2371 0.2605 0.042 Uiso 1 1 calc R . . C10 C 0.5197(2) 0.22026(16) 0.21470(8) 0.0305(3) Uani 1 1 d . . . H10A H 0.5025 0.1277 0.2164 0.037 Uiso 1 1 calc R . . O11 O 0.2692(2) 0.24115(14) 0.13128(7) 0.0485(4) Uani 1 1 d . . . C11 C 0.2530(3) 0.16011(18) 0.07532(8) 0.0404(4) Uani 1 1 d . . . H11A H 0.2402 0.2111 0.0345 0.048 Uiso 1 1 calc R . . C11M C 0.0766(3) 0.0774(3) 0.08300(12) 0.0556(6) Uani 1 1 d . . . H11B H -0.0418 0.1285 0.0821 0.083 Uiso 1 1 calc R . . H11C H 0.0844 0.0329 0.1249 0.083 Uiso 1 1 calc R . . H11D H 0.0726 0.0170 0.0470 0.083 Uiso 1 1 calc R . . O12 O 0.57953(19) 0.18795(13) 0.09810(6) 0.0397(3) Uani 1 1 d . . . C12 C 0.4488(3) 0.09292(17) 0.07542(8) 0.0346(4) Uani 1 1 d . . . H12A H 0.4458 0.0223 0.1074 0.041 Uiso 1 1 calc R . . C12M C 0.5174(3) 0.04670(18) 0.00891(9) 0.0389(4) Uani 1 1 d . . . H12B H 0.6442 0.0056 0.0137 0.058 Uiso 1 1 calc R . . H12C H 0.5300 0.1175 -0.0212 0.058 Uiso 1 1 calc R . . H12D H 0.4224 -0.0128 -0.0087 0.058 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 C1 0.0364(9) 0.0466(10) 0.0279(8) -0.0063(7) -0.0034(7) 0.0112(8) C2 0.0764(15) 0.0445(10) 0.0326(9) 0.0038(8) 0.0000(10) 0.0141(11) C3 0.0766(15) 0.0427(10) 0.0441(11) 0.0054(8) 0.0110(12) -0.0080(11) C4 0.0413(10) 0.0478(10) 0.0395(9) -0.0039(8) 0.0059(8) -0.0081(9) C5 0.0251(8) 0.0455(10) 0.0311(8) -0.0020(7) 0.0024(6) 0.0013(7) C6 0.0261(8) 0.0592(11) 0.0369(9) 0.0030(8) -0.0034(7) 0.0051(8) C7 0.0319(8) 0.0448(9) 0.0293(8) 0.0015(7) -0.0021(6) -0.0019(8) C7M 0.0452(11) 0.0664(13) 0.0351(10) 0.0074(9) -0.0091(8) 0.0007(10) C8 0.0293(8) 0.0424(9) 0.0295(8) -0.0037(7) 0.0008(7) -0.0035(7) C8M 0.0324(9) 0.0608(12) 0.0357(9) -0.0120(9) 0.0026(7) -0.0033(9) C9 0.0241(8) 0.0487(10) 0.0323(8) -0.0048(7) -0.0016(6) 0.0047(7) C10 0.0273(8) 0.0354(8) 0.0287(8) -0.0019(7) -0.0015(6) 0.0039(7) O11 0.0378(7) 0.0681(9) 0.0397(7) -0.0194(6) -0.0108(6) 0.0212(7) C11 0.0417(10) 0.0483(10) 0.0311(8) -0.0056(7) -0.0082(8) 0.0138(9) C11M 0.0361(10) 0.0749(15) 0.0558(13) -0.0140(11) -0.0014(9) 0.0052(11) O12 0.0357(7) 0.0506(7) 0.0328(6) -0.0104(5) -0.0020(5) 0.0079(6) C12 0.0346(8) 0.0406(9) 0.0285(8) -0.0005(7) -0.0019(7) 0.0079(8) C12M 0.0432(10) 0.0409(9) 0.0326(9) -0.0051(7) 0.0010(7) 0.0017(8) _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 O12 1.439(2) . ? C1 O11 1.440(2) . ? C1 C2 1.520(3) . ? C1 C10 1.541(2) . ? C2 C3 1.527(4) . ? C3 C4 1.538(3) . ? C4 C5 1.535(3) . ? C5 C6 1.533(2) . ? C5 C10 1.537(2) . ? C6 C7 1.519(3) . ? C7 C8 1.335(2) . ? C7 C7M 1.517(2) . ? C8 C8M 1.512(2) . ? C8 C9 1.524(2) . ? C9 C10 1.536(2) . ? O11 C11 1.439(2) . ? C11 C11M 1.509(3) . ? C11 C12 1.524(2) . ? O12 C12 1.434(2) . ? C12 C12M 1.519(2) . ? 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 O12 C1 O11 106.39(14) . . ? O12 C1 C2 107.81(16) . . ? O11 C1 C2 111.28(18) . . ? O12 C1 C10 109.78(14) . . ? O11 C1 C10 109.07(15) . . ? C2 C1 C10 112.33(16) . . ? C1 C2 C3 112.80(18) . . ? C2 C3 C4 111.35(18) . . ? C5 C4 C3 109.93(16) . . ? C6 C5 C4 112.99(16) . . ? C6 C5 C10 109.92(14) . . ? C4 C5 C10 111.23(15) . . ? C7 C6 C5 114.49(15) . . ? C8 C7 C7M 124.36(17) . . ? C8 C7 C6 122.36(16) . . ? C7M C7 C6 113.25(16) . . ? C7 C8 C8M 124.34(16) . . ? C7 C8 C9 122.45(15) . . ? C8M C8 C9 113.20(15) . . ? C8 C9 C10 114.14(14) . . ? C9 C10 C5 111.66(14) . . ? C9 C10 C1 111.94(14) . . ? C5 C10 C1 110.41(14) . . ? C11 O11 C1 108.60(14) . . ? O11 C11 C11M 109.56(17) . . ? O11 C11 C12 102.52(14) . . ? C11M C11 C12 115.36(16) . . ? C12 O12 C1 106.85(14) . . ? O12 C12 C12M 109.03(15) . . ? O12 C12 C11 102.42(14) . . ? C12M C12 C11 115.23(15) . . ? 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 O12 C1 C2 C3 -69.0(2) . . . . ? O11 C1 C2 C3 174.68(16) . . . . ? C10 C1 C2 C3 52.1(2) . . . . ? C1 C2 C3 C4 -53.5(2) . . . . ? C2 C3 C4 C5 56.1(2) . . . . ? C3 C4 C5 C6 177.38(16) . . . . ? C3 C4 C5 C10 -58.4(2) . . . . ? C4 C5 C6 C7 80.2(2) . . . . ? C10 C5 C6 C7 -44.7(2) . . . . ? C5 C6 C7 C8 16.5(3) . . . . ? C5 C6 C7 C7M -165.53(18) . . . . ? C7M C7 C8 C8M 3.4(3) . . . . ? C6 C7 C8 C8M -178.88(19) . . . . ? C7M C7 C8 C9 -177.4(2) . . . . ? C6 C7 C8 C9 0.4(3) . . . . ? C7 C8 C9 C10 12.6(3) . . . . ? C8M C8 C9 C10 -168.11(16) . . . . ? C8 C9 C10 C5 -41.6(2) . . . . ? C8 C9 C10 C1 -165.98(15) . . . . ? C6 C5 C10 C9 57.44(19) . . . . ? C4 C5 C10 C9 -68.46(19) . . . . ? C6 C5 C10 C1 -177.33(15) . . . . ? C4 C5 C10 C1 56.77(18) . . . . ? O12 C1 C10 C9 -168.12(15) . . . . ? O11 C1 C10 C9 -51.9(2) . . . . ? C2 C1 C10 C9 71.9(2) . . . . ? O12 C1 C10 C5 66.81(19) . . . . ? O11 C1 C10 C5 -176.99(14) . . . . ? C2 C1 C10 C5 -53.1(2) . . . . ? O12 C1 O11 C11 -3.4(2) . . . . ? C2 C1 O11 C11 113.74(17) . . . . ? C10 C1 O11 C11 -121.78(16) . . . . ? C1 O11 C11 C11M 146.72(17) . . . . ? C1 O11 C11 C12 23.7(2) . . . . ? O11 C1 O12 C12 -20.08(18) . . . . ? C2 C1 O12 C12 -139.54(16) . . . . ? C10 C1 O12 C12 97.80(16) . . . . ? C1 O12 C12 C12M 156.62(14) . . . . ? C1 O12 C12 C11 34.09(17) . . . . ? O11 C11 C12 O12 -35.11(17) . . . . ? C11M C11 C12 O12 -154.10(16) . . . . ? O11 C11 C12 C12M -153.33(17) . . . . ? C11M C11 C12 C12M 87.7(2) . . . . ? _diffrn_measured_fraction_theta_max 0.907 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.25 _refine_diff_density_min -0.19 _refine_diff_density_rms 0.04 #===END data_compound22 _database_code_CSD 210315 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H26 O3' _chemical_formula_sum 'C16 H26 O3' _chemical_formula_weight 266.37 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _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 5.9429(10) _cell_length_b 12.548(2) _cell_length_c 20.128(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1500.9(8) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3413 _cell_measurement_theta_min 2.6 _cell_measurement_theta_max 27.1 _exptl_crystal_description tablet _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.179 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type none _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 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART1000 CCD area detector' _diffrn_measurement_method omega _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 9505 _diffrn_reflns_av_R_equivalents 0.040 _diffrn_reflns_av_sigmaI/netI 0.036 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 29.00 _reflns_number_total 2110 _reflns_number_gt 1680 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART version 5.624 (Bruker, 2001)' _computing_cell_refinement 'Bruker SAINT version 6.02a (Bruker, 2000)' _computing_data_reduction 'Bruker SAINT; Bruker SHELXTL (Bruker, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'SHELXL-97; PLATON (Spek, 2002)' _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^)+(0.053P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens 'placed geometrically' _refine_ls_hydrogen_treatment 'riding model' _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 'not determinable' _refine_ls_number_reflns 2110 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0479 _refine_ls_R_factor_gt 0.0365 _refine_ls_wR_factor_ref 0.0876 _refine_ls_wR_factor_gt 0.0834 _refine_ls_goodness_of_fit_ref 0.98 _refine_ls_restrained_S_all 0.98 _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 0.7402(3) 0.40694(12) 0.24538(8) 0.0243(4) Uani 1 1 d . . . C2 C 0.6041(3) 0.51026(13) 0.24403(8) 0.0293(4) Uani 1 1 d . . . H2A H 0.6100 0.5415 0.1989 0.035 Uiso 1 1 calc R . . H2B H 0.4448 0.4946 0.2546 0.035 Uiso 1 1 calc R . . C3 C 0.6966(4) 0.59004(13) 0.29404(9) 0.0315(4) Uani 1 1 d . . . H3A H 0.8499 0.6119 0.2805 0.038 Uiso 1 1 calc R . . H3B H 0.6002 0.6544 0.2944 0.038 Uiso 1 1 calc R . . C4 C 0.7047(3) 0.54237(12) 0.36340(8) 0.0279(4) Uani 1 1 d . . . H4A H 0.5494 0.5277 0.3787 0.033 Uiso 1 1 calc R . . H4B H 0.7724 0.5947 0.3943 0.033 Uiso 1 1 calc R . . C5 C 0.8415(3) 0.43902(12) 0.36559(8) 0.0239(4) Uani 1 1 d . . . H5A H 0.9991 0.4571 0.3524 0.029 Uiso 1 1 calc R . . C6 C 0.8508(3) 0.39369(13) 0.43727(8) 0.0306(4) Uani 1 1 d . . . H6A H 0.9581 0.3323 0.4362 0.037 Uiso 1 1 calc R . . C6M C 0.9443(4) 0.47308(15) 0.48784(9) 0.0461(6) Uani 1 1 d . . . H6MA H 0.9470 0.4400 0.5319 0.069 Uiso 1 1 calc R . . H6MB H 0.8484 0.5366 0.4889 0.069 Uiso 1 1 calc R . . H6MC H 1.0975 0.4935 0.4751 0.069 Uiso 1 1 calc R . . O7 O 0.5367(3) 0.36802(11) 0.51048(7) 0.0522(4) Uani 1 1 d . . . C7 C 0.6242(3) 0.34849(14) 0.45711(9) 0.0340(4) Uani 1 1 d . . . C8 C 0.5174(3) 0.27326(14) 0.40783(9) 0.0345(4) Uani 1 1 d . . . H8A H 0.3601 0.2592 0.4215 0.041 Uiso 1 1 calc R . . H8B H 0.5994 0.2046 0.4087 0.041 Uiso 1 1 calc R . . C9 C 0.5181(3) 0.31681(13) 0.33680(8) 0.0270(4) Uani 1 1 d . . . H9A H 0.4113 0.3772 0.3338 0.032 Uiso 1 1 calc R . . H9B H 0.4659 0.2604 0.3060 0.032 Uiso 1 1 calc R . . C10 C 0.7530(3) 0.35466(12) 0.31523(8) 0.0219(3) Uani 1 1 d . . . C10M C 0.9119(3) 0.25839(13) 0.31110(9) 0.0283(4) Uani 1 1 d . . . H10A H 1.0618 0.2823 0.2974 0.042 Uiso 1 1 calc R . . H10B H 0.8536 0.2073 0.2785 0.042 Uiso 1 1 calc R . . H10C H 0.9217 0.2241 0.3547 0.042 Uiso 1 1 calc R . . O11 O 0.6472(2) 0.33160(9) 0.19993(5) 0.0276(3) Uani 1 1 d . . . C11 C 0.7694(3) 0.34400(14) 0.13873(8) 0.0300(4) Uani 1 1 d . . . H11A H 0.7073 0.4055 0.1130 0.036 Uiso 1 1 calc R . . C11M C 0.7482(4) 0.24255(15) 0.09836(9) 0.0455(5) Uani 1 1 d . . . H11B H 0.5910 0.2325 0.0851 0.068 Uiso 1 1 calc R . . H11C H 0.7971 0.1817 0.1253 0.068 Uiso 1 1 calc R . . H11D H 0.8429 0.2478 0.0586 0.068 Uiso 1 1 calc R . . C12 C 1.0052(3) 0.36998(14) 0.16289(8) 0.0287(4) Uani 1 1 d . . . H12A H 1.0865 0.3028 0.1747 0.034 Uiso 1 1 calc R . . C12M C 1.1439(3) 0.43466(16) 0.11452(9) 0.0395(5) Uani 1 1 d . . . H12B H 1.2930 0.4481 0.1336 0.059 Uiso 1 1 calc R . . H12C H 1.0685 0.5027 0.1058 0.059 Uiso 1 1 calc R . . H12D H 1.1602 0.3951 0.0728 0.059 Uiso 1 1 calc R . . O12 O 0.9622(2) 0.43126(9) 0.22185(6) 0.0282(3) 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 C1 0.0229(9) 0.0255(8) 0.0245(9) -0.0004(7) -0.0007(7) -0.0034(7) C2 0.0338(11) 0.0280(9) 0.0262(9) 0.0047(7) -0.0033(8) 0.0040(8) C3 0.0410(11) 0.0216(8) 0.0321(10) 0.0020(7) -0.0024(8) 0.0035(8) C4 0.0359(11) 0.0207(8) 0.0270(9) 0.0000(7) -0.0026(8) 0.0010(7) C5 0.0259(9) 0.0214(8) 0.0245(8) 0.0016(7) -0.0018(7) -0.0008(7) C6 0.0411(11) 0.0245(8) 0.0261(9) 0.0006(7) -0.0057(8) 0.0055(8) C6M 0.0722(17) 0.0361(10) 0.0300(10) -0.0012(8) -0.0168(11) 0.0019(11) O7 0.0708(11) 0.0515(8) 0.0342(8) 0.0042(7) 0.0164(8) 0.0102(8) C7 0.0438(12) 0.0286(9) 0.0296(9) 0.0096(7) 0.0040(8) 0.0112(9) C8 0.0339(11) 0.0338(10) 0.0357(10) 0.0075(8) 0.0085(8) -0.0057(9) C9 0.0236(9) 0.0279(8) 0.0294(9) -0.0001(7) 0.0019(7) -0.0031(7) C10 0.0206(8) 0.0207(8) 0.0245(8) 0.0007(6) 0.0000(7) -0.0011(7) C10M 0.0285(10) 0.0258(8) 0.0308(9) -0.0006(7) 0.0009(8) 0.0023(8) O11 0.0274(7) 0.0309(6) 0.0244(6) -0.0031(5) 0.0003(5) -0.0062(5) C11 0.0326(10) 0.0349(9) 0.0226(8) 0.0007(7) 0.0016(7) -0.0036(8) C11M 0.0531(13) 0.0499(12) 0.0334(10) -0.0116(9) 0.0048(10) -0.0112(12) C12 0.0314(10) 0.0308(9) 0.0238(8) 0.0015(7) 0.0026(7) 0.0008(8) C12M 0.0339(11) 0.0548(12) 0.0298(10) 0.0051(9) 0.0036(8) -0.0072(10) O12 0.0261(7) 0.0329(6) 0.0255(6) -0.0006(5) 0.0026(5) -0.0064(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O11 1.427(2) . ? C1 O12 1.435(2) . ? C1 C2 1.528(2) . ? C1 C10 1.553(2) . ? C2 C3 1.522(2) . ? C3 C4 1.520(2) . ? C4 C5 1.531(2) . ? C5 C6 1.552(2) . ? C5 C10 1.557(2) . ? C6 C7 1.515(3) . ? C6 C6M 1.529(2) . ? O7 C7 1.218(2) . ? C7 C8 1.509(3) . ? C8 C9 1.531(2) . ? C9 C10 1.537(2) . ? C10 C10M 1.536(2) . ? O11 C11 1.438(2) . ? C11 C11M 1.515(2) . ? C11 C12 1.519(3) . ? C12 O12 1.437(2) . ? C12 C12M 1.512(2) . ? 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 O11 C1 O12 106.59(13) . . ? O11 C1 C2 110.20(14) . . ? O12 C1 C2 107.48(13) . . ? O11 C1 C10 108.63(12) . . ? O12 C1 C10 110.11(14) . . ? C2 C1 C10 113.59(14) . . ? C3 C2 C1 110.78(15) . . ? C4 C3 C2 111.11(14) . . ? C3 C4 C5 112.13(14) . . ? C4 C5 C6 110.86(14) . . ? C4 C5 C10 112.19(14) . . ? C6 C5 C10 111.59(12) . . ? C7 C6 C6M 113.05(17) . . ? C7 C6 C5 110.54(15) . . ? C6M C6 C5 113.15(14) . . ? O7 C7 C8 121.71(19) . . ? O7 C7 C6 122.46(19) . . ? C8 C7 C6 115.78(15) . . ? C7 C8 C9 112.92(14) . . ? C8 C9 C10 112.13(15) . . ? C10M C10 C9 109.31(13) . . ? C10M C10 C1 108.25(13) . . ? C9 C10 C1 109.99(14) . . ? C10M C10 C5 111.23(13) . . ? C9 C10 C5 109.46(14) . . ? C1 C10 C5 108.58(12) . . ? C1 O11 C11 106.37(13) . . ? O11 C11 C11M 109.06(14) . . ? O11 C11 C12 102.40(13) . . ? C11M C11 C12 115.37(17) . . ? O12 C12 C12M 109.97(14) . . ? O12 C12 C11 102.44(14) . . ? C12M C12 C11 114.34(15) . . ? C1 O12 C12 108.80(13) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O11 C1 C2 C3 178.04(14) . . . . ? O12 C1 C2 C3 -66.18(17) . . . . ? C10 C1 C2 C3 55.9(2) . . . . ? C1 C2 C3 C4 -55.4(2) . . . . ? C2 C3 C4 C5 56.1(2) . . . . ? C3 C4 C5 C6 178.81(15) . . . . ? C3 C4 C5 C10 -55.69(19) . . . . ? C4 C5 C6 C7 71.89(17) . . . . ? C10 C5 C6 C7 -53.94(18) . . . . ? C4 C5 C6 C6M -56.1(2) . . . . ? C10 C5 C6 C6M 178.11(16) . . . . ? C6M C6 C7 O7 -5.4(2) . . . . ? C5 C6 C7 O7 -133.36(18) . . . . ? C6M C6 C7 C8 177.35(15) . . . . ? C5 C6 C7 C8 49.36(19) . . . . ? O7 C7 C8 C9 134.40(18) . . . . ? C6 C7 C8 C9 -48.3(2) . . . . ? C7 C8 C9 C10 51.0(2) . . . . ? C8 C9 C10 C10M 66.18(18) . . . . ? C8 C9 C10 C1 -175.10(13) . . . . ? C8 C9 C10 C5 -55.88(17) . . . . ? O11 C1 C10 C10M 62.36(18) . . . . ? O12 C1 C10 C10M -54.02(16) . . . . ? C2 C1 C10 C10M -174.62(14) . . . . ? O11 C1 C10 C9 -57.02(17) . . . . ? O12 C1 C10 C9 -173.40(13) . . . . ? C2 C1 C10 C9 66.00(17) . . . . ? O11 C1 C10 C5 -176.77(13) . . . . ? O12 C1 C10 C5 66.84(16) . . . . ? C2 C1 C10 C5 -53.76(19) . . . . ? C4 C5 C10 C10M 171.87(14) . . . . ? C6 C5 C10 C10M -63.03(19) . . . . ? C4 C5 C10 C9 -67.22(17) . . . . ? C6 C5 C10 C9 57.87(18) . . . . ? C4 C5 C10 C1 52.86(18) . . . . ? C6 C5 C10 C1 177.96(15) . . . . ? O12 C1 O11 C11 -22.33(16) . . . . ? C2 C1 O11 C11 94.00(16) . . . . ? C10 C1 O11 C11 -140.96(14) . . . . ? C1 O11 C11 C11M 157.91(15) . . . . ? C1 O11 C11 C12 35.21(17) . . . . ? O11 C11 C12 O12 -34.56(16) . . . . ? C11M C11 C12 O12 -152.88(14) . . . . ? O11 C11 C12 C12M -153.48(14) . . . . ? C11M C11 C12 C12M 88.2(2) . . . . ? O11 C1 O12 C12 -0.76(16) . . . . ? C2 C1 O12 C12 -118.90(15) . . . . ? C10 C1 O12 C12 116.89(13) . . . . ? C12M C12 O12 C1 143.82(14) . . . . ? C11 C12 O12 C1 21.87(17) . . . . ? _diffrn_measured_fraction_theta_max 0.913 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.24 _refine_diff_density_min -0.18 _refine_diff_density_rms 0.04 #===END data_compound31 _database_code_CSD 210316 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H34 O4' _chemical_formula_weight 374.50 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 Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' 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 6.1489(9) _cell_length_b 14.787(2) _cell_length_c 23.008(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2092.0(5) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 62420 _cell_measurement_theta_min 2.9 _cell_measurement_theta_max 27.5 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.189 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 816 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.83 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_process_details ; Using multiple and symmetry-related data measurements via the program SORTAV See R.H. Blessing, Acta Crysta (1995), A51, 33-38 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enraf Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf Nonius KappaCCD area detector' _diffrn_measurement_method 'Phi and Omega scans to fill Ewald sphere' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9146 _diffrn_reflns_av_R_equivalents 0.136 _diffrn_reflns_av_sigmaI/netI 0.1123 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 3.28 _diffrn_reflns_theta_max 27.50 _reflns_number_total 2361 _reflns_number_gt 1639 _reflns_threshold_expression >2sigma(I) loop_ _computing_data_collection ' DENZO (Otwinowski and Minor, 1997' ' COLLECT (Hooft, 1998)' _computing_cell_refinement 'DENZO and COLLECT' _computing_data_reduction 'DENZO and COLLECT' _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^)+(0.0346P)^2^+2.8401P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens 'geometrically placed, Me 7M and 8M from delta-F' _refine_ls_hydrogen_treatment 'riding model, Me as rigid rotating group' _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.020(3) _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 1(4) #unreliable from Mo data with O heaviest atom _refine_ls_number_reflns 2341 _refine_ls_number_parameters 247 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1432 _refine_ls_R_factor_gt 0.0934 _refine_ls_wR_factor_ref 0.1767 _refine_ls_wR_factor_gt 0.1562 _refine_ls_goodness_of_fit_ref 1.129 _refine_ls_restrained_S_all 1.129 _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 0.5001(10) 0.0606(4) 0.6050(2) 0.0290(16) Uani 1 1 d . . . H1A H 0.3744 0.0971 0.6195 0.035 Uiso 1 1 calc R . . C2 C 0.6777(11) 0.1246(5) 0.5855(2) 0.0351(17) Uani 1 1 d . . . H2A H 0.8096 0.0898 0.5751 0.042 Uiso 1 1 calc R . . H2B H 0.7155 0.1663 0.6177 0.042 Uiso 1 1 calc R . . C3 C 0.6005(12) 0.1785(5) 0.5333(2) 0.0355(17) Uani 1 1 d . . . H3A H 0.7225 0.2155 0.5183 0.043 Uiso 1 1 calc R . . H3B H 0.4833 0.2202 0.5456 0.043 Uiso 1 1 calc R . . C4 C 0.5157(11) 0.1175(5) 0.4846(2) 0.0366(18) Uani 1 1 d . . . H4A H 0.4569 0.1555 0.4528 0.044 Uiso 1 1 calc R . . H4B H 0.6372 0.0813 0.4687 0.044 Uiso 1 1 calc R . . C5 C 0.3378(10) 0.0543(5) 0.5068(2) 0.0331(17) Uani 1 1 d . . . H5A H 0.2161 0.0928 0.5215 0.040 Uiso 1 1 calc R . . C6 C 0.2461(11) -0.0055(5) 0.4578(2) 0.0312(15) Uani 1 1 d . . . H6A H 0.1001 -0.0273 0.4694 0.037 Uiso 1 1 calc R . . H6B H 0.2286 0.0317 0.4224 0.037 Uiso 1 1 calc R . . C7 C 0.3862(11) -0.0857(4) 0.4435(2) 0.0306(17) Uani 1 1 d . . . C7M C 0.3194(12) -0.1321(5) 0.3875(2) 0.0423(19) Uani 1 1 d . . . H7M1 H 0.4288 -0.1775 0.3770 0.063 Uiso 1 1 calc R . . H7M2 H 0.3080 -0.0871 0.3564 0.063 Uiso 1 1 calc R . . H7M3 H 0.1783 -0.1617 0.3930 0.063 Uiso 1 1 calc R . . C8 C 0.5462(11) -0.1140(5) 0.4781(2) 0.0308(16) Uani 1 1 d . . . C8M C 0.6988(12) -0.1914(5) 0.4646(3) 0.047(2) Uani 1 1 d . . . H8M1 H 0.6678 -0.2146 0.4256 0.071 Uiso 1 1 calc R . . H8M2 H 0.6780 -0.2397 0.4932 0.071 Uiso 1 1 calc R . . H8M3 H 0.8494 -0.1699 0.4663 0.071 Uiso 1 1 calc R . . C9 C 0.5958(11) -0.0695(4) 0.5358(2) 0.0310(16) Uani 1 1 d . . . H9A H 0.7330 -0.0349 0.5321 0.037 Uiso 1 1 calc R . . H9B H 0.6192 -0.1172 0.5653 0.037 Uiso 1 1 calc R . . C10 C 0.4167(9) -0.0053(5) 0.5577(2) 0.0264(14) Uani 1 1 d . . . C10M C 0.2278(10) -0.0597(5) 0.5824(2) 0.0351(17) Uani 1 1 d . . . H10A H 0.1734 -0.1015 0.5527 0.053 Uiso 1 1 calc R . . H10B H 0.1109 -0.0185 0.5941 0.053 Uiso 1 1 calc R . . H10C H 0.2775 -0.0942 0.6163 0.053 Uiso 1 1 calc R . . O11 O 0.5889(6) 0.0070(3) 0.65422(14) 0.0304(11) Uani 1 1 d . . . O12 O 0.3036(7) 0.0434(3) 0.71238(15) 0.0367(12) Uani 1 1 d . . . C12 C 0.4755(10) 0.0079(4) 0.7045(2) 0.0271(15) Uani 1 1 d . . . C13 C 0.6044(10) -0.0425(4) 0.7509(2) 0.0278(15) Uani 1 1 d . . . O14 O 0.4483(7) -0.0633(3) 0.79724(14) 0.0309(11) Uani 1 1 d . . . O15 O 0.4521(7) -0.1625(3) 0.87110(16) 0.0414(13) Uani 1 1 d . . . C15 C 0.5474(10) -0.1302(5) 0.8299(2) 0.0303(16) Uani 1 1 d . . . C16 C 0.7664(10) -0.1468(4) 0.8050(2) 0.0276(16) Uani 1 1 d . . . C16M C 0.8752(10) -0.2327(5) 0.8247(2) 0.0337(17) Uani 1 1 d . . . H16A H 0.9002 -0.2300 0.8668 0.051 Uiso 1 1 calc R . . H16B H 1.0146 -0.2396 0.8046 0.051 Uiso 1 1 calc R . . H16C H 0.7814 -0.2844 0.8157 0.051 Uiso 1 1 calc R . . C17 C 0.8945(10) -0.0587(4) 0.8188(2) 0.0310(16) Uani 1 1 d . . . H17A H 1.0501 -0.0653 0.8086 0.037 Uiso 1 1 calc R . . H17B H 0.8824 -0.0428 0.8605 0.037 Uiso 1 1 calc R . . C18 C 0.7826(10) 0.0141(4) 0.7800(2) 0.0295(16) Uani 1 1 d . . . H18A H 0.7205 0.0637 0.8036 0.035 Uiso 1 1 calc R . . H18B H 0.8848 0.0396 0.7510 0.035 Uiso 1 1 calc R . . C19 C 0.7104(10) -0.1355(5) 0.7394(2) 0.0286(16) Uani 1 1 d . . . C20 C 0.5492(11) -0.2071(5) 0.7176(2) 0.0382(18) Uani 1 1 d . . . H20A H 0.5195 -0.1971 0.6763 0.057 Uiso 1 1 calc R . . H20B H 0.4133 -0.2024 0.7397 0.057 Uiso 1 1 calc R . . H20C H 0.6117 -0.2675 0.7230 0.057 Uiso 1 1 calc R . . C21 C 0.9093(10) -0.1354(5) 0.7002(2) 0.0359(17) Uani 1 1 d . . . H21A H 0.8635 -0.1283 0.6597 0.054 Uiso 1 1 calc R . . H21B H 0.9877 -0.1927 0.7047 0.054 Uiso 1 1 calc R . . H21C H 1.0050 -0.0852 0.7111 0.054 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 C1 0.035(4) 0.034(4) 0.018(3) 0.004(3) -0.002(3) 0.007(3) C2 0.036(4) 0.044(5) 0.025(3) -0.002(3) 0.002(3) 0.000(4) C3 0.048(4) 0.038(5) 0.021(3) 0.004(3) 0.000(3) -0.003(4) C4 0.046(4) 0.047(5) 0.017(3) 0.002(3) 0.001(3) -0.001(4) C5 0.031(3) 0.052(5) 0.017(3) -0.001(3) -0.004(3) 0.001(4) C6 0.040(4) 0.036(4) 0.018(3) 0.009(3) -0.004(3) 0.000(3) C7 0.041(4) 0.031(5) 0.020(3) 0.003(3) 0.000(3) -0.008(3) C7M 0.061(5) 0.042(5) 0.024(3) -0.003(3) -0.003(3) -0.001(4) C8 0.039(4) 0.031(4) 0.023(3) -0.001(3) 0.006(3) -0.003(4) C8M 0.051(5) 0.050(6) 0.041(4) -0.001(3) 0.010(4) -0.003(4) C9 0.034(4) 0.035(4) 0.024(3) 0.006(3) -0.002(3) 0.001(3) C10 0.023(3) 0.038(4) 0.019(2) 0.004(3) -0.003(2) 0.001(3) C10M 0.038(4) 0.042(5) 0.026(3) 0.005(3) -0.003(3) 0.006(4) O11 0.029(2) 0.045(3) 0.0168(18) 0.0007(18) -0.0031(18) 0.005(2) O12 0.034(3) 0.052(3) 0.025(2) 0.008(2) 0.0015(19) 0.010(2) C12 0.022(3) 0.036(4) 0.023(3) -0.002(3) 0.003(2) -0.006(3) C13 0.027(3) 0.042(5) 0.014(2) -0.002(3) 0.000(2) -0.001(3) O14 0.035(2) 0.039(3) 0.0182(18) 0.0036(18) 0.0053(19) 0.007(2) O15 0.047(3) 0.054(3) 0.022(2) 0.004(2) 0.009(2) 0.005(3) C15 0.039(4) 0.035(5) 0.017(3) -0.002(3) 0.000(3) -0.006(4) C16 0.032(4) 0.029(5) 0.022(3) 0.002(3) 0.002(3) 0.002(3) C16M 0.033(4) 0.043(5) 0.025(3) -0.001(3) 0.001(3) -0.002(4) C17 0.038(4) 0.040(5) 0.015(3) -0.005(3) -0.005(3) -0.003(4) C18 0.034(4) 0.035(4) 0.020(3) -0.001(3) 0.001(3) 0.000(3) C19 0.029(3) 0.041(5) 0.016(3) -0.003(3) -0.002(2) -0.003(4) C20 0.038(4) 0.055(5) 0.021(3) 0.001(3) -0.004(3) -0.007(4) C21 0.036(4) 0.050(5) 0.022(3) 0.001(3) 0.003(3) 0.003(4) _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 O11 1.486(6) . ? C1 C2 1.514(9) . ? C1 C10 1.548(8) . ? C2 C3 1.518(8) . ? C3 C4 1.530(8) . ? C4 C5 1.526(8) . ? C5 C6 1.540(8) . ? C5 C10 1.545(8) . ? C6 C7 1.502(9) . ? C7 C8 1.332(8) . ? C7 C7M 1.517(8) . ? C8 C8M 1.511(9) . ? C8 C9 1.514(8) . ? C9 C10 1.538(8) . ? C10 C10M 1.523(8) . ? O11 C12 1.351(6) . ? O12 C12 1.194(7) . ? C12 C13 1.524(8) . ? C13 O14 1.467(6) . ? C13 C18 1.532(8) . ? C13 C19 1.546(9) . ? O14 C15 1.384(7) . ? O15 C15 1.212(7) . ? C15 C16 1.485(9) . ? C16 C16M 1.506(8) . ? C16 C17 1.555(8) . ? C16 C19 1.557(7) . ? C17 C18 1.558(8) . ? C19 C21 1.519(8) . ? C19 C20 1.534(8) . ? 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 O11 C1 C2 107.1(5) . . ? O11 C1 C10 108.8(5) . . ? C2 C1 C10 115.1(5) . . ? C1 C2 C3 109.7(5) . . ? C2 C3 C4 112.2(5) . . ? C5 C4 C3 111.1(5) . . ? C4 C5 C6 111.7(4) . . ? C4 C5 C10 112.2(5) . . ? C6 C5 C10 110.0(5) . . ? C7 C6 C5 113.8(5) . . ? C8 C7 C6 122.8(5) . . ? C8 C7 C7M 124.4(6) . . ? C6 C7 C7M 112.8(6) . . ? C7 C8 C8M 125.0(6) . . ? C7 C8 C9 122.4(6) . . ? C8M C8 C9 112.6(6) . . ? C8 C9 C10 114.3(5) . . ? C10M C10 C9 110.0(5) . . ? C10M C10 C5 110.2(5) . . ? C9 C10 C5 109.2(4) . . ? C10M C10 C1 108.8(4) . . ? C9 C10 C1 112.4(5) . . ? C5 C10 C1 106.2(5) . . ? C12 O11 C1 117.3(5) . . ? O12 C12 O11 126.2(6) . . ? O12 C12 C13 124.7(5) . . ? O11 C12 C13 109.1(5) . . ? O14 C13 C12 105.7(4) . . ? O14 C13 C18 105.4(4) . . ? C12 C13 C18 114.2(5) . . ? O14 C13 C19 102.4(5) . . ? C12 C13 C19 122.3(4) . . ? C18 C13 C19 105.1(5) . . ? C15 O14 C13 104.9(4) . . ? O15 C15 O14 119.6(6) . . ? O15 C15 C16 132.5(6) . . ? O14 C15 C16 107.8(5) . . ? C15 C16 C16M 115.2(5) . . ? C15 C16 C17 104.0(5) . . ? C16M C16 C17 114.8(5) . . ? C15 C16 C19 99.0(4) . . ? C16M C16 C19 118.8(5) . . ? C17 C16 C19 102.8(5) . . ? C16 C17 C18 103.8(5) . . ? C13 C18 C17 100.9(5) . . ? C21 C19 C20 109.1(5) . . ? C21 C19 C13 116.1(5) . . ? C20 C19 C13 113.5(5) . . ? C21 C19 C16 113.4(5) . . ? C20 C19 C16 112.7(5) . . ? C13 C19 C16 91.2(4) . . ? 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 O11 C1 C2 C3 177.4(5) . . . . ? C10 C1 C2 C3 56.3(7) . . . . ? C1 C2 C3 C4 -53.0(7) . . . . ? C2 C3 C4 C5 54.8(7) . . . . ? C3 C4 C5 C6 178.3(6) . . . . ? C3 C4 C5 C10 -57.6(7) . . . . ? C4 C5 C6 C7 79.9(6) . . . . ? C10 C5 C6 C7 -45.5(7) . . . . ? C5 C6 C7 C8 14.5(8) . . . . ? C5 C6 C7 C7M -167.8(5) . . . . ? C6 C7 C8 C8M -177.0(6) . . . . ? C7M C7 C8 C8M 5.6(10) . . . . ? C6 C7 C8 C9 2.1(9) . . . . ? C7M C7 C8 C9 -175.3(6) . . . . ? C7 C8 C9 C10 13.8(9) . . . . ? C8M C8 C9 C10 -167.1(5) . . . . ? C8 C9 C10 C10M 76.7(6) . . . . ? C8 C9 C10 C5 -44.3(7) . . . . ? C8 C9 C10 C1 -161.8(5) . . . . ? C4 C5 C10 C10M 174.0(5) . . . . ? C6 C5 C10 C10M -61.0(6) . . . . ? C4 C5 C10 C9 -65.1(6) . . . . ? C6 C5 C10 C9 60.0(7) . . . . ? C4 C5 C10 C1 56.3(6) . . . . ? C6 C5 C10 C1 -178.6(5) . . . . ? O11 C1 C10 C10M 64.2(6) . . . . ? C2 C1 C10 C10M -175.6(5) . . . . ? O11 C1 C10 C9 -57.9(6) . . . . ? C2 C1 C10 C9 62.3(6) . . . . ? O11 C1 C10 C5 -177.2(4) . . . . ? C2 C1 C10 C5 -57.0(6) . . . . ? C2 C1 O11 C12 124.8(5) . . . . ? C10 C1 O11 C12 -110.2(5) . . . . ? C1 O11 C12 O12 4.7(9) . . . . ? C1 O11 C12 C13 -174.2(5) . . . . ? O12 C12 C13 O14 18.3(8) . . . . ? O11 C12 C13 O14 -162.8(4) . . . . ? O12 C12 C13 C18 -97.2(7) . . . . ? O11 C12 C13 C18 81.7(6) . . . . ? O12 C12 C13 C19 134.4(6) . . . . ? O11 C12 C13 C19 -46.7(7) . . . . ? C12 C13 O14 C15 162.9(5) . . . . ? C18 C13 O14 C15 -75.7(6) . . . . ? C19 C13 O14 C15 33.9(5) . . . . ? C13 O14 C15 O15 -178.3(5) . . . . ? C13 O14 C15 C16 2.5(6) . . . . ? O15 C15 C16 C16M 15.9(9) . . . . ? O14 C15 C16 C16M -165.0(5) . . . . ? O15 C15 C16 C17 -110.6(8) . . . . ? O14 C15 C16 C17 68.5(5) . . . . ? O15 C15 C16 C19 143.7(7) . . . . ? O14 C15 C16 C19 -37.2(6) . . . . ? C15 C16 C17 C18 -68.2(5) . . . . ? C16M C16 C17 C18 165.1(5) . . . . ? C19 C16 C17 C18 34.7(6) . . . . ? O14 C13 C18 C17 70.1(5) . . . . ? C12 C13 C18 C17 -174.3(5) . . . . ? C19 C13 C18 C17 -37.6(5) . . . . ? C16 C17 C18 C13 1.3(5) . . . . ? O14 C13 C19 C21 -170.0(4) . . . . ? C12 C13 C19 C21 72.2(7) . . . . ? C18 C13 C19 C21 -60.1(5) . . . . ? O14 C13 C19 C20 62.3(5) . . . . ? C12 C13 C19 C20 -55.5(7) . . . . ? C18 C13 C19 C20 172.3(4) . . . . ? O14 C13 C19 C16 -53.1(5) . . . . ? C12 C13 C19 C16 -170.9(5) . . . . ? C18 C13 C19 C16 56.8(5) . . . . ? C15 C16 C19 C21 171.9(6) . . . . ? C16M C16 C19 C21 -62.7(8) . . . . ? C17 C16 C19 C21 65.2(7) . . . . ? C15 C16 C19 C20 -63.5(6) . . . . ? C16M C16 C19 C20 61.8(7) . . . . ? C17 C16 C19 C20 -170.2(5) . . . . ? C15 C16 C19 C13 52.6(5) . . . . ? C16M C16 C19 C13 178.0(5) . . . . ? C17 C16 C19 C13 -54.1(5) . . . . ? _diffrn_measured_fraction_theta_max 0.850 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.872 _refine_diff_density_max 0.259 _refine_diff_density_min -0.240 _refine_diff_density_rms 0.059