# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2009 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Antonio Echavarren' _publ_contact_author_email AECHAVARREN@ICIQ.ES _publ_section_title ; Stereoselective Gold-Catalyzed Cycloaddition of Functionalized Ketoenynes: Synthesis of (+)-Orientalol F ; loop_ _publ_author_name 'Antonio Echavarren' 'Eloisa Jimenez-Nunez' 'Kian Molawi' # Attachment 'E20847_0m.cif' data_e20847_0m _database_code_depnum_ccdc_archive 'CCDC 747563' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H24 O3' _chemical_formula_weight 252.34 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.7861(5) _cell_length_b 8.9090(5) _cell_length_c 9.9947(6) _cell_angle_alpha 106.620(3) _cell_angle_beta 93.492(4) _cell_angle_gamma 109.880(3) _cell_volume 694.03(7) _cell_formula_units_Z 2 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 2325 _cell_measurement_theta_min 2.77 _cell_measurement_theta_max 31.61 _exptl_crystal_description PLATE _exptl_crystal_colour white _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.208 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 276 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.98680 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; SADABS Version 2.1 2003 Bruker-Nonius Blessing, Acta Cryst. (1995) A51 33-38 ; _exptl_special_details ; It should be noted that the esd's of the cell dimensions are probably too low; they should be multiplied by a factor of 2 to 10 ; _diffrn_ambient_temperature 100(2) _diffrn_measurement_specimen_suppport 'magnetic support whith 10 micron nylon fiber cryoloop' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_source 'rotating anode X-ray tube' _diffrn_source_type 'Bruker-Nonius FR 591' _diffrn_source_power 50 _diffrn_source_current 70 _diffrn_source_size '3 mm x 0.3 mm fine focus' _diffrn_radiation_monochromator 'Multilayer Montel 200 mirrors' _diffrn_detector_type '4K CCD area detector APEX II' _diffrn_measurement_device_type 'Kappa 4-axis goniometer bruker-nonius' _diffrn_measurement_method ; Fullsphere data collection, phi and omega scans ; _diffrn_detector_area_resol_mean 512 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11917 _diffrn_reflns_av_R_equivalents 0.0462 _diffrn_reflns_av_sigmaI/netI 0.0590 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.77 _diffrn_reflns_theta_max 32.29 _reflns_number_total 4520 _reflns_number_gt 3149 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker-Nonius Apex v1.0-22 2002' _computing_cell_refinement 'Bruker-Nonius Apex v1.0-22 2002' _computing_data_reduction 'SAINT+ Version 7.06A Bruker-Nonius, 2004' _computing_structure_solution 'Shelxtl Version 6.12 (Sheldrick, 2001)' _computing_structure_refinement 'Shelxtl Version 6.12 (Sheldrick, 2001)' _computing_molecular_graphics 'Shelxtl Version 6.12 (Sheldrick, 2001)' _computing_publication_material 'Shelxtl Version 6.12 (Sheldrick, 2001)' _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^)+(0.1087P)^2^+0.0626P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4520 _refine_ls_number_parameters 168 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0928 _refine_ls_R_factor_gt 0.0616 _refine_ls_wR_factor_ref 0.1838 _refine_ls_wR_factor_gt 0.1632 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.20901(12) 0.19789(12) 0.64260(12) 0.0148(2) Uani 1 1 d . . . C1 C -0.21668(16) 0.24796(18) 0.77213(17) 0.0150(3) Uani 1 1 d . . . O2 O 0.07107(11) 0.42440(13) 0.88533(12) 0.0154(2) Uani 1 1 d . . . C2 C -0.25131(18) 0.1360(2) 0.8703(2) 0.0214(3) Uani 1 1 d . . . H2A H -0.2518 0.2031 0.9656 0.026 Uiso 1 1 calc R . . H2B H -0.3577 0.0445 0.8346 0.026 Uiso 1 1 calc R . . O3 O -0.24258(12) 0.40041(14) 0.82733(13) 0.0190(3) Uani 1 1 d . . . H3 H -0.1828 0.4557 0.9046 0.028 Uiso 1 1 calc R . . C3 C -0.11338(19) 0.0640(2) 0.8720(2) 0.0215(3) Uani 1 1 d . . . H3A H -0.0432 0.1129 0.9644 0.026 Uiso 1 1 calc R . . H3B H -0.1598 -0.0578 0.8486 0.026 Uiso 1 1 calc R . . C4 C -0.01651(16) 0.11427(18) 0.75840(17) 0.0155(3) Uani 1 1 d . . . H4 H -0.0810 0.0334 0.6668 0.019 Uiso 1 1 calc R . . C5 C 0.16241(17) 0.12650(18) 0.75468(17) 0.0155(3) Uani 1 1 d . . . C6 C 0.25237(16) 0.37721(17) 0.70792(16) 0.0130(3) Uani 1 1 d . . . C7 C 0.09645(16) 0.41241(17) 0.74088(16) 0.0135(3) Uani 1 1 d . . . H7 H 0.0663 0.4868 0.6980 0.016 Uiso 1 1 calc R . . C8 C -0.03541(16) 0.27808(17) 0.76831(16) 0.0133(3) Uani 1 1 d . . . C9 C 0.28971(17) 0.25415(19) 0.88727(18) 0.0175(3) Uani 1 1 d . . . H9A H 0.2368 0.2768 0.9690 0.021 Uiso 1 1 calc R . . H9B H 0.3730 0.2117 0.9088 0.021 Uiso 1 1 calc R . . C10 C 0.36569(16) 0.41464(18) 0.84622(17) 0.0162(3) Uani 1 1 d . . . H10A H 0.3654 0.5136 0.9189 0.019 Uiso 1 1 calc R . . H10B H 0.4776 0.4321 0.8311 0.019 Uiso 1 1 calc R . . C11 C -0.32422(18) 0.1578(2) 0.62645(18) 0.0209(3) Uani 1 1 d . . . H11A H -0.4365 0.1416 0.6349 0.031 Uiso 1 1 calc R . . H11B H -0.3154 0.0501 0.5863 0.031 Uiso 1 1 calc R . . H11C H -0.2887 0.2248 0.5660 0.031 Uiso 1 1 calc R . . C12 C 0.1723(2) -0.0464(2) 0.7117(2) 0.0221(3) Uani 1 1 d . . . H12A H 0.1033 -0.1143 0.6213 0.033 Uiso 1 1 calc R . . H12B H 0.1361 -0.0993 0.7814 0.033 Uiso 1 1 calc R . . H12C H 0.2839 -0.0355 0.7051 0.033 Uiso 1 1 calc R . . C13 C 0.33785(16) 0.46466(18) 0.60692(17) 0.0157(3) Uani 1 1 d . . . H13 H 0.4290 0.4272 0.5855 0.019 Uiso 1 1 calc R . . C14 C 0.41286(19) 0.65678(19) 0.6790(2) 0.0213(3) Uani 1 1 d . . . H14A H 0.4678 0.7092 0.6146 0.032 Uiso 1 1 calc R . . H14B H 0.4905 0.6839 0.7624 0.032 Uiso 1 1 calc R . . H14C H 0.3273 0.6976 0.7053 0.032 Uiso 1 1 calc R . . C15 C 0.22524(18) 0.4148(2) 0.46629(19) 0.0212(3) Uani 1 1 d . . . H15A H 0.1850 0.2945 0.4221 0.032 Uiso 1 1 calc R . . H15B H 0.2856 0.4687 0.4050 0.032 Uiso 1 1 calc R . . H15C H 0.1342 0.4499 0.4832 0.032 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 O1 0.0130(4) 0.0139(4) 0.0156(5) 0.0011(4) 0.0039(4) 0.0055(3) C1 0.0082(5) 0.0199(6) 0.0143(7) 0.0011(5) 0.0023(5) 0.0057(5) O2 0.0091(4) 0.0202(5) 0.0118(5) -0.0017(4) 0.0000(4) 0.0053(4) C2 0.0141(6) 0.0297(8) 0.0223(8) 0.0092(7) 0.0085(6) 0.0089(6) O3 0.0117(5) 0.0252(5) 0.0168(6) -0.0013(4) 0.0001(4) 0.0101(4) C3 0.0167(6) 0.0279(8) 0.0240(9) 0.0121(7) 0.0079(6) 0.0096(6) C4 0.0109(6) 0.0180(6) 0.0164(7) 0.0036(5) 0.0031(5) 0.0053(5) C5 0.0128(6) 0.0172(6) 0.0172(7) 0.0044(5) 0.0042(5) 0.0071(5) C6 0.0086(5) 0.0143(6) 0.0140(7) 0.0001(5) 0.0020(5) 0.0056(4) C7 0.0100(5) 0.0170(6) 0.0122(7) 0.0008(5) 0.0030(5) 0.0067(5) C8 0.0081(5) 0.0182(6) 0.0103(6) 0.0009(5) 0.0005(5) 0.0045(5) C9 0.0125(6) 0.0237(7) 0.0175(8) 0.0047(6) 0.0013(5) 0.0099(5) C10 0.0093(5) 0.0182(6) 0.0178(7) 0.0009(5) 0.0005(5) 0.0058(5) C11 0.0114(6) 0.0266(7) 0.0179(8) -0.0005(6) -0.0022(5) 0.0059(5) C12 0.0205(7) 0.0194(7) 0.0294(9) 0.0073(6) 0.0091(6) 0.0111(6) C13 0.0098(5) 0.0176(6) 0.0175(7) 0.0023(5) 0.0045(5) 0.0049(5) C14 0.0180(7) 0.0178(6) 0.0253(9) 0.0043(6) 0.0049(6) 0.0052(5) C15 0.0149(6) 0.0276(7) 0.0187(8) 0.0073(6) 0.0040(6) 0.0050(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C6 1.4432(17) . ? O1 C5 1.4538(19) . ? C1 O3 1.4134(19) . ? C1 C11 1.518(2) . ? C1 C8 1.5273(19) . ? C1 C2 1.562(2) . ? O2 C8 1.4517(17) . ? O2 C7 1.4535(19) . ? C2 C3 1.553(2) . ? C3 C4 1.537(2) . ? C4 C8 1.500(2) . ? C4 C5 1.542(2) . ? C5 C12 1.511(2) . ? C5 C9 1.547(2) . ? C6 C13 1.528(2) . ? C6 C10 1.535(2) . ? C6 C7 1.540(2) . ? C7 C8 1.460(2) . ? C9 C10 1.542(2) . ? C13 C15 1.525(2) . ? C13 C14 1.534(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 C6 O1 C5 104.88(11) . . ? O3 C1 C11 106.25(12) . . ? O3 C1 C8 112.19(11) . . ? C11 C1 C8 112.88(13) . . ? O3 C1 C2 113.51(14) . . ? C11 C1 C2 112.43(12) . . ? C8 C1 C2 99.75(11) . . ? C8 O2 C7 60.36(9) . . ? C3 C2 C1 107.87(13) . . ? C4 C3 C2 104.52(13) . . ? C8 C4 C3 101.19(13) . . ? C8 C4 C5 112.28(11) . . ? C3 C4 C5 123.51(13) . . ? O1 C5 C12 107.64(14) . . ? O1 C5 C4 104.19(11) . . ? C12 C5 C4 111.23(12) . . ? O1 C5 C9 103.81(11) . . ? C12 C5 C9 113.34(12) . . ? C4 C5 C9 115.59(13) . . ? O1 C6 C13 107.75(12) . . ? O1 C6 C10 102.11(11) . . ? C13 C6 C10 113.91(11) . . ? O1 C6 C7 109.33(10) . . ? C13 C6 C7 112.92(12) . . ? C10 C6 C7 110.17(13) . . ? O2 C7 C8 59.76(9) . . ? O2 C7 C6 112.97(11) . . ? C8 C7 C6 116.47(12) . . ? O2 C8 C7 59.88(9) . . ? O2 C8 C4 115.95(11) . . ? C7 C8 C4 119.84(13) . . ? O2 C8 C1 111.62(12) . . ? C7 C8 C1 131.79(13) . . ? C4 C8 C1 106.57(11) . . ? C10 C9 C5 104.38(12) . . ? C6 C10 C9 103.26(11) . . ? C15 C13 C6 112.56(11) . . ? C15 C13 C14 111.84(13) . . ? C6 C13 C14 110.75(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 O3 C1 C2 C3 -138.02(13) . . . . ? C11 C1 C2 C3 101.34(15) . . . . ? C8 C1 C2 C3 -18.50(16) . . . . ? C1 C2 C3 C4 -7.96(17) . . . . ? C2 C3 C4 C8 31.71(15) . . . . ? C2 C3 C4 C5 158.19(14) . . . . ? C6 O1 C5 C12 -160.77(11) . . . . ? C6 O1 C5 C4 81.04(12) . . . . ? C6 O1 C5 C9 -40.35(13) . . . . ? C8 C4 C5 O1 -51.42(16) . . . . ? C3 C4 C5 O1 -172.94(13) . . . . ? C8 C4 C5 C12 -167.11(14) . . . . ? C3 C4 C5 C12 71.36(19) . . . . ? C8 C4 C5 C9 61.79(17) . . . . ? C3 C4 C5 C9 -59.73(19) . . . . ? C5 O1 C6 C13 167.86(10) . . . . ? C5 O1 C6 C10 47.60(13) . . . . ? C5 O1 C6 C7 -69.07(13) . . . . ? C8 O2 C7 C6 -108.26(13) . . . . ? O1 C6 C7 O2 95.05(13) . . . . ? C13 C6 C7 O2 -145.02(12) . . . . ? C10 C6 C7 O2 -16.40(15) . . . . ? O1 C6 C7 C8 28.62(17) . . . . ? C13 C6 C7 C8 148.56(13) . . . . ? C10 C6 C7 C8 -82.83(15) . . . . ? C7 O2 C8 C4 110.94(15) . . . . ? C7 O2 C8 C1 -126.78(14) . . . . ? C6 C7 C8 O2 102.38(13) . . . . ? O2 C7 C8 C4 -104.50(14) . . . . ? C6 C7 C8 C4 -2.1(2) . . . . ? O2 C7 C8 C1 93.03(17) . . . . ? C6 C7 C8 C1 -164.59(15) . . . . ? C3 C4 C8 O2 78.89(14) . . . . ? C5 C4 C8 O2 -54.68(18) . . . . ? C3 C4 C8 C7 147.53(13) . . . . ? C5 C4 C8 C7 14.0(2) . . . . ? C3 C4 C8 C1 -46.02(15) . . . . ? C5 C4 C8 C1 -179.59(12) . . . . ? O3 C1 C8 O2 32.97(17) . . . . ? C11 C1 C8 O2 152.97(12) . . . . ? C2 C1 C8 O2 -87.51(14) . . . . ? O3 C1 C8 C7 -35.3(2) . . . . ? C11 C1 C8 C7 84.7(2) . . . . ? C2 C1 C8 C7 -155.81(16) . . . . ? O3 C1 C8 C4 160.48(13) . . . . ? C11 C1 C8 C4 -79.51(16) . . . . ? C2 C1 C8 C4 40.01(16) . . . . ? O1 C5 C9 C10 16.65(14) . . . . ? C12 C5 C9 C10 133.14(14) . . . . ? C4 C5 C9 C10 -96.78(14) . . . . ? O1 C6 C10 C9 -35.08(14) . . . . ? C13 C6 C10 C9 -150.94(13) . . . . ? C7 C6 C10 C9 80.99(14) . . . . ? C5 C9 C10 C6 10.99(15) . . . . ? O1 C6 C13 C15 63.33(15) . . . . ? C10 C6 C13 C15 175.84(13) . . . . ? C7 C6 C13 C15 -57.51(17) . . . . ? O1 C6 C13 C14 -170.65(11) . . . . ? C10 C6 C13 C14 -58.14(16) . . . . ? C7 C6 C13 C14 68.51(15) . . . . ? _diffrn_measured_fraction_theta_max 0.914 _diffrn_reflns_theta_full 32.29 _diffrn_measured_fraction_theta_full 0.914 _refine_diff_density_max 0.606 _refine_diff_density_min -0.324 _refine_diff_density_rms 0.078 # Attachment 'e20849P21c.cif' data_e20849p21c _database_code_depnum_ccdc_archive 'CCDC 747564' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H24 O2' _chemical_formula_weight 236.34 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 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 15.8542(4) _cell_length_b 7.8544(2) _cell_length_c 11.0204(3) _cell_angle_alpha 90.00 _cell_angle_beta 108.2520(10) _cell_angle_gamma 90.00 _cell_volume 1303.27(6) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8353 _cell_measurement_theta_min 4.06 _cell_measurement_theta_max 39.27 _exptl_crystal_description BLOCK _exptl_crystal_colour white _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.60 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.205 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 520 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.98500 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; SADABS Version 2.1 2003 Bruker-Nonius Blessing, Acta Cryst. (1995) A51 33-38 ; _exptl_special_details ; It should be noted that the esd's of the cell dimensions are probably too low; they should be multiplied by a factor of 2 to 10 ; _diffrn_ambient_temperature 100(2) _diffrn_measurement_specimen_suppport 'magnetic support whith 10 micron nylon fiber cryoloop' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_source 'rotating anode X-ray tube' _diffrn_source_type 'Bruker-Nonius FR 591' _diffrn_source_power 50 _diffrn_source_current 70 _diffrn_source_size '3 mm x 0.3 mm fine focus' _diffrn_radiation_monochromator 'Multilayer Montel 200 mirrors' _diffrn_detector_type '4K CCD area detector APEX II' _diffrn_measurement_device_type 'Kappa 4-axis goniometer bruker-nonius' _diffrn_measurement_method ; Fullsphere data collection, phi and omega scans ; _diffrn_detector_area_resol_mean 512 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 30679 _diffrn_reflns_av_R_equivalents 0.0191 _diffrn_reflns_av_sigmaI/netI 0.0179 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.74 _diffrn_reflns_theta_max 39.32 _reflns_number_total 7505 _reflns_number_gt 6632 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker-Nonius Apex v1.0-22 2002' _computing_cell_refinement 'Bruker-Nonius Apex v1.0-22 2002' _computing_data_reduction 'SAINT+ Version 7.06A Bruker-Nonius, 2004' _computing_structure_solution 'Shelxtl Version 6.12 (Sheldrick, 2001)' _computing_structure_refinement 'Shelxtl Version 6.12 (Sheldrick, 2001)' _computing_molecular_graphics 'Shelxtl Version 6.12 (Sheldrick, 2001)' _computing_publication_material 'Shelxtl Version 6.12 (Sheldrick, 2001)' _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^)+(0.0632P)^2^+0.1657P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7505 _refine_ls_number_parameters 159 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0430 _refine_ls_R_factor_gt 0.0374 _refine_ls_wR_factor_ref 0.1137 _refine_ls_wR_factor_gt 0.1092 _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_restrained_S_all 1.081 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.21699(2) 0.59706(5) 0.40545(3) 0.01288(6) Uani 1 1 d . . . C1 C 0.17263(3) 0.58304(6) 0.50159(4) 0.01255(7) Uani 1 1 d . . . O2 O 0.19485(3) 0.64017(5) 0.72292(4) 0.01662(7) Uani 1 1 d . . . H2 H 0.2030 0.7299 0.7665 0.025 Uiso 1 1 calc R . . C2 C 0.23733(3) 0.65442(6) 0.62753(4) 0.01226(7) Uani 1 1 d . . . H2A H 0.2480 0.7777 0.6149 0.015 Uiso 1 1 calc R . . C3 C 0.32458(3) 0.56117(6) 0.65884(4) 0.01183(7) Uani 1 1 d . . . C4 C 0.38298(3) 0.51500(6) 0.77111(4) 0.01307(7) Uani 1 1 d . . . C5 C 0.46358(3) 0.43126(7) 0.75077(5) 0.01562(8) Uani 1 1 d . . . H5A H 0.4805 0.3270 0.8033 0.019 Uiso 1 1 calc R . . H5B H 0.5148 0.5102 0.7725 0.019 Uiso 1 1 calc R . . C6 C 0.43298(3) 0.38802(7) 0.60771(5) 0.01722(9) Uani 1 1 d . . . H6A H 0.4109 0.2695 0.5931 0.021 Uiso 1 1 calc R . . H6B H 0.4822 0.4022 0.5712 0.021 Uiso 1 1 calc R . . C7 C 0.35785(3) 0.51577(6) 0.54806(4) 0.01276(7) Uani 1 1 d . . . H7 H 0.3851 0.6202 0.5241 0.015 Uiso 1 1 calc R . . C8 C 0.28129(3) 0.45936(6) 0.43068(4) 0.01280(7) Uani 1 1 d . . . C9 C 0.22828(3) 0.30811(7) 0.45775(5) 0.01694(8) Uani 1 1 d . . . H9A H 0.2679 0.2275 0.5185 0.020 Uiso 1 1 calc R . . H9B H 0.1970 0.2466 0.3779 0.020 Uiso 1 1 calc R . . C10 C 0.16160(3) 0.38938(7) 0.51615(5) 0.01606(8) Uani 1 1 d . . . H10A H 0.1755 0.3577 0.6073 0.019 Uiso 1 1 calc R . . H10B H 0.1002 0.3529 0.4696 0.019 Uiso 1 1 calc R . . C11 C 0.08471(3) 0.68227(7) 0.45812(5) 0.01674(9) Uani 1 1 d . . . H11 H 0.0507 0.6510 0.5175 0.020 Uiso 1 1 calc R . . C12 C 0.09671(4) 0.87593(8) 0.46525(5) 0.02145(10) Uani 1 1 d . . . H12A H 0.1360 0.9100 0.4163 0.032 Uiso 1 1 calc R . . H12B H 0.1230 0.9105 0.5546 0.032 Uiso 1 1 calc R . . H12C H 0.0388 0.9312 0.4294 0.032 Uiso 1 1 calc R . . C13 C 0.02757(4) 0.63071(9) 0.32330(5) 0.02266(11) Uani 1 1 d . . . H13A H -0.0317 0.6810 0.3047 0.034 Uiso 1 1 calc R . . H13B H 0.0225 0.5064 0.3180 0.034 Uiso 1 1 calc R . . H13C H 0.0554 0.6718 0.2610 0.034 Uiso 1 1 calc R . . C14 C 0.38108(4) 0.54422(7) 0.90415(4) 0.01730(9) Uani 1 1 d . . . H14A H 0.4284 0.6238 0.9479 0.026 Uiso 1 1 calc R . . H14B H 0.3901 0.4358 0.9505 0.026 Uiso 1 1 calc R . . H14C H 0.3234 0.5922 0.9013 0.026 Uiso 1 1 calc R . . C15 C 0.31054(4) 0.43808(7) 0.31305(5) 0.01816(9) Uani 1 1 d . . . H15A H 0.2584 0.4174 0.2384 0.027 Uiso 1 1 calc R . . H15B H 0.3513 0.3413 0.3253 0.027 Uiso 1 1 calc R . . H15C H 0.3407 0.5418 0.2995 0.027 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 O1 0.01283(13) 0.01561(15) 0.01162(12) 0.00176(10) 0.00587(10) 0.00241(10) C1 0.01151(15) 0.01566(18) 0.01130(15) 0.00000(12) 0.00476(12) -0.00032(12) O2 0.01711(15) 0.02162(17) 0.01384(14) -0.00326(12) 0.00874(11) -0.00123(12) C2 0.01193(15) 0.01410(17) 0.01162(15) -0.00052(12) 0.00495(12) 0.00035(12) C3 0.01185(15) 0.01211(16) 0.01169(15) -0.00006(12) 0.00391(12) 0.00012(12) C4 0.01360(16) 0.01258(17) 0.01217(15) 0.00004(12) 0.00282(12) -0.00037(12) C5 0.01346(17) 0.01558(19) 0.01612(17) 0.00029(14) 0.00216(13) 0.00162(13) C6 0.01611(18) 0.0193(2) 0.01600(18) -0.00011(14) 0.00467(14) 0.00576(15) C7 0.01217(16) 0.01392(17) 0.01288(15) 0.00055(12) 0.00490(12) 0.00139(12) C8 0.01391(16) 0.01347(17) 0.01188(15) -0.00005(12) 0.00528(12) 0.00144(12) C9 0.01948(19) 0.01407(19) 0.01853(19) -0.00213(14) 0.00776(15) -0.00227(14) C10 0.01652(18) 0.0167(2) 0.01627(18) -0.00068(14) 0.00700(14) -0.00369(14) C11 0.01163(16) 0.0250(2) 0.01421(17) 0.00122(15) 0.00489(13) 0.00279(14) C12 0.0214(2) 0.0238(2) 0.0195(2) 0.00109(17) 0.00677(16) 0.00969(18) C13 0.01449(19) 0.0342(3) 0.01668(19) 0.00095(18) 0.00118(15) -0.00082(18) C14 0.0199(2) 0.0187(2) 0.01185(16) -0.00005(14) 0.00288(14) 0.00099(15) C15 0.0211(2) 0.0217(2) 0.01398(17) 0.00001(15) 0.00880(15) 0.00426(16) _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 1.4478(5) . ? O1 C8 1.4522(6) . ? C1 C11 1.5367(7) . ? C1 C10 1.5452(7) . ? C1 C2 1.5496(6) . ? O2 C2 1.4194(6) . ? C2 C3 1.5066(6) . ? C3 C4 1.3424(6) . ? C3 C7 1.5163(6) . ? C4 C14 1.4936(7) . ? C4 C5 1.5151(7) . ? C5 C6 1.5353(7) . ? C6 C7 1.5387(7) . ? C7 C8 1.5360(6) . ? C8 C15 1.5164(7) . ? C8 C9 1.5374(7) . ? C9 C10 1.5380(7) . ? C11 C12 1.5319(9) . ? C11 C13 1.5326(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 C1 O1 C8 106.03(3) . . ? O1 C1 C11 109.54(4) . . ? O1 C1 C10 104.33(4) . . ? C11 C1 C10 114.24(4) . . ? O1 C1 C2 106.91(3) . . ? C11 C1 C2 112.16(4) . . ? C10 C1 C2 109.14(4) . . ? O2 C2 C3 113.99(4) . . ? O2 C2 C1 107.47(4) . . ? C3 C2 C1 109.39(4) . . ? C4 C3 C2 131.39(4) . . ? C4 C3 C7 111.42(4) . . ? C2 C3 C7 117.12(4) . . ? C3 C4 C14 130.03(4) . . ? C3 C4 C5 110.55(4) . . ? C14 C4 C5 119.29(4) . . ? C4 C5 C6 103.77(4) . . ? C5 C6 C7 104.35(4) . . ? C3 C7 C8 111.32(4) . . ? C3 C7 C6 103.14(4) . . ? C8 C7 C6 118.26(4) . . ? O1 C8 C15 107.62(4) . . ? O1 C8 C7 105.58(4) . . ? C15 C8 C7 112.28(4) . . ? O1 C8 C9 102.65(4) . . ? C15 C8 C9 114.38(4) . . ? C7 C8 C9 113.28(4) . . ? C8 C9 C10 104.46(4) . . ? C9 C10 C1 104.48(4) . . ? C12 C11 C13 109.78(5) . . ? C12 C11 C1 113.68(4) . . ? C13 C11 C1 111.79(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 C8 O1 C1 C11 -161.49(4) . . . . ? C8 O1 C1 C10 -38.79(4) . . . . ? C8 O1 C1 C2 76.77(4) . . . . ? O1 C1 C2 O2 -179.56(4) . . . . ? C11 C1 C2 O2 60.37(5) . . . . ? C10 C1 C2 O2 -67.26(5) . . . . ? O1 C1 C2 C3 -55.31(5) . . . . ? C11 C1 C2 C3 -175.39(4) . . . . ? C10 C1 C2 C3 56.98(5) . . . . ? O2 C2 C3 C4 -24.74(7) . . . . ? C1 C2 C3 C4 -145.08(5) . . . . ? O2 C2 C3 C7 158.74(4) . . . . ? C1 C2 C3 C7 38.40(5) . . . . ? C2 C3 C4 C14 -1.17(9) . . . . ? C7 C3 C4 C14 175.51(5) . . . . ? C2 C3 C4 C5 -176.91(5) . . . . ? C7 C3 C4 C5 -0.24(6) . . . . ? C3 C4 C5 C6 -15.77(6) . . . . ? C14 C4 C5 C6 167.97(4) . . . . ? C4 C5 C6 C7 24.69(5) . . . . ? C4 C3 C7 C8 143.87(4) . . . . ? C2 C3 C7 C8 -38.93(5) . . . . ? C4 C3 C7 C6 16.06(5) . . . . ? C2 C3 C7 C6 -166.74(4) . . . . ? C5 C6 C7 C3 -24.66(5) . . . . ? C5 C6 C7 C8 -147.98(4) . . . . ? C1 O1 C8 C15 164.39(4) . . . . ? C1 O1 C8 C7 -75.51(4) . . . . ? C1 O1 C8 C9 43.38(4) . . . . ? C3 C7 C8 O1 54.66(5) . . . . ? C6 C7 C8 O1 173.79(4) . . . . ? C3 C7 C8 C15 171.66(4) . . . . ? C6 C7 C8 C15 -69.21(6) . . . . ? C3 C7 C8 C9 -56.90(5) . . . . ? C6 C7 C8 C9 62.24(5) . . . . ? O1 C8 C9 C10 -30.15(5) . . . . ? C15 C8 C9 C10 -146.40(4) . . . . ? C7 C8 C9 C10 83.20(5) . . . . ? C8 C9 C10 C1 7.38(5) . . . . ? O1 C1 C10 C9 18.09(5) . . . . ? C11 C1 C10 C9 137.66(4) . . . . ? C2 C1 C10 C9 -95.89(4) . . . . ? O1 C1 C11 C12 -72.94(5) . . . . ? C10 C1 C11 C12 170.46(4) . . . . ? C2 C1 C11 C12 45.60(5) . . . . ? O1 C1 C11 C13 52.03(6) . . . . ? C10 C1 C11 C13 -64.57(6) . . . . ? C2 C1 C11 C13 170.57(4) . . . . ? _diffrn_measured_fraction_theta_max 0.971 _diffrn_reflns_theta_full 39.32 _diffrn_measured_fraction_theta_full 0.971 _refine_diff_density_max 0.556 _refine_diff_density_min -0.227 _refine_diff_density_rms 0.053