# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2002 data_global loop_ _publ_author_name _publ_author_address 'Sorensen, John' ; Department of Chemistry University of Alberta Edmonton Alberta T6G 2G2 Canada ; 'Auclair, Karine' ; Department of Chemistry McGill University Otto Maass Chemistry Building 801 Sherbrooke Street West Montreal, Quebec H3A 2K6 Canada ; 'Kennedy, Jonathan' ; Kosan Biosciences Inc. 3832 Bay Center Place Hayward, California 94545 U. S. A. ; 'Hutchinson, C. Richard' ; Kosan Biosciences Inc. 3832 Bay Center Place Hayward, California 94545 U. S. A. ; 'Vederas, John C.' ; Department of Chemistry University of Alberta Edmonton Alberta T6G 2G2 Canada ; _publ_contact_author_name 'Dr John C. Vederas' _publ_contact_author_address ; Department of Chemistry University of Alberta Edmonton Alberta T6G 2G2 Canada ; _publ_contact_author_email john.vederas@ualberta.ca _publ_contact_author_fax '1(780)4928231' _publ_contact_author_phone '1(780)4925475' _publ_contact_letter ; To: Cambridge Crystallographic Data Centre Please accept the following CIF data which are featured in a manuscript being submitted to Journal of the Chemical Society, Perkin Transactions 1. Please forward any questions concerning this CIF to Bob McDonald (Bob.McDonald@ualberta.ca). ; _publ_requested_journal 'Organic & Biomolecular Chemistry' _publ_section_title ; Transformations of cyclic nonaketides by Aspergillus terreus mutants blocked for lovastatin biosynthesis at the lovA and lovC genes ; data_jcv9901 _database_code_CSD 191453 _audit_creation_method 'manual editing of SHELXL template' _chemical_formula_sum 'C19 H30 O3' _chemical_formula_weight 306.43 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 5.5947(9) _cell_length_b 9.6504(17) _cell_length_c 31.930(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1723.9(5) _cell_formula_units_Z 4 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 1217 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.181 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 672 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9786 _exptl_absorpt_correction_T_max 0.9992 _exptl_absorpt_process_details ? _diffrn_ambient_temperature 193(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4/RA diffractometer/SAMRT 1000 CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.192 _diffrn_standards_number 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 3287 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.4618 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 38 _diffrn_reflns_theta_min 1.28 _diffrn_reflns_theta_max 25.84 _reflns_number_total 3287 _reflns_number_gt 899 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART (Bruker, 1997)' _computing_cell_refinement 'Bruker SAINT (Bruker, 1997)' _computing_data_reduction 'Bruker SAINT (Bruker, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL (Sheldrick, 1997)' _computing_publication_material 'Bruker SHELXTL (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0758P)^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 constr _refine_ls_extinction_method none _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0(5) _refine_ls_number_reflns 3287 _refine_ls_number_parameters 200 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2881 _refine_ls_R_factor_gt 0.0620 _refine_ls_wR_factor_ref 0.2159 _refine_ls_wR_factor_gt 0.1103 _refine_ls_goodness_of_fit_ref 0.779 _refine_ls_restrained_S_all 0.779 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_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_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 0.4532(8) -0.2735(6) -0.21692(17) 0.0296(16) Uani 1 1 d . . . O2 O 0.7411(9) -0.3456(6) -0.25793(17) 0.0350(16) Uani 1 1 d . . . O3 O 0.1803(9) -0.5838(6) -0.2059(2) 0.0375(17) Uani 1 1 d . . . H3O H 0.2048 -0.6607 -0.2175 0.056 Uiso 1 1 calc R . . C1 C -0.0419(13) -0.0160(8) -0.1172(3) 0.026(2) Uani 1 1 d . . . H1 H 0.1052 -0.0053 -0.0997 0.031 Uiso 1 1 calc R . . C2 C -0.0516(12) 0.1101(9) -0.1467(2) 0.023(2) Uani 1 1 d . . . H2 H 0.1123 0.1220 -0.1587 0.028 Uiso 1 1 calc R . . C3 C -0.1076(13) 0.2406(9) -0.1222(3) 0.031(2) Uani 1 1 d . . . H3 H -0.0824 0.3272 -0.1357 0.038 Uiso 1 1 calc R . . C4 C -0.1884(14) 0.2422(9) -0.0837(3) 0.033(2) Uani 1 1 d . . . H4 H -0.2204 0.3293 -0.0710 0.039 Uiso 1 1 calc R . . C5 C -0.2323(12) 0.1150(8) -0.0591(2) 0.023(2) Uani 1 1 d . . . H5 H -0.0895 0.1001 -0.0408 0.027 Uiso 1 1 calc R . . C6 C -0.4509(12) 0.1313(9) -0.0301(3) 0.030(2) Uani 1 1 d . . . H6A H -0.4275 0.2127 -0.0117 0.036 Uiso 1 1 calc R . . H6B H -0.5953 0.1478 -0.0473 0.036 Uiso 1 1 calc R . . C7 C -0.4885(14) 0.0030(9) -0.0033(3) 0.031(2) Uani 1 1 d . . . H7 H -0.6476 0.0132 0.0106 0.037 Uiso 1 1 calc R . . C8 C -0.5015(13) -0.1266(9) -0.0307(3) 0.035(2) Uani 1 1 d . . . H8A H -0.5094 -0.2093 -0.0124 0.043 Uiso 1 1 calc R . . H8B H -0.6508 -0.1235 -0.0474 0.043 Uiso 1 1 calc R . . C9 C -0.2905(14) -0.1421(8) -0.0604(2) 0.030(2) Uani 1 1 d . . . H9A H -0.3178 -0.2227 -0.0790 0.035 Uiso 1 1 calc R . . H9B H -0.1436 -0.1600 -0.0440 0.035 Uiso 1 1 calc R . . C10 C -0.2554(14) -0.0114(8) -0.0872(2) 0.022(2) Uani 1 1 d . . . H10 H -0.4028 0.0010 -0.1045 0.026 Uiso 1 1 calc R . . C11 C -0.2247(13) 0.0970(8) -0.1839(2) 0.033(2) Uani 1 1 d . . . H11A H -0.2157 0.1808 -0.2011 0.040 Uiso 1 1 calc R . . H11B H -0.3881 0.0854 -0.1734 0.040 Uiso 1 1 calc R . . H11C H -0.1805 0.0163 -0.2009 0.040 Uiso 1 1 calc R . . C12 C -0.3012(15) -0.0116(9) 0.0316(3) 0.049(3) Uani 1 1 d . . . H12A H -0.2985 0.0732 0.0485 0.059 Uiso 1 1 calc R . . H12B H -0.1432 -0.0266 0.0192 0.059 Uiso 1 1 calc R . . H12C H -0.3423 -0.0906 0.0495 0.059 Uiso 1 1 calc R . . C13 C -0.0181(12) -0.1556(9) -0.1406(2) 0.028(2) Uani 1 1 d . . . H13A H -0.0161 -0.2323 -0.1200 0.033 Uiso 1 1 calc R . . H13B H -0.1582 -0.1688 -0.1591 0.033 Uiso 1 1 calc R . . C14 C 0.2104(13) -0.1601(8) -0.1667(2) 0.029(2) Uani 1 1 d . . . H14A H 0.3484 -0.1381 -0.1485 0.035 Uiso 1 1 calc R . . H14B H 0.2015 -0.0878 -0.1887 0.035 Uiso 1 1 calc R . . C15 C 0.2531(14) -0.3017(8) -0.1877(2) 0.025(2) Uani 1 1 d . . . H15 H 0.1079 -0.3286 -0.2041 0.030 Uiso 1 1 calc R . . C16 C 0.3153(14) -0.4165(8) -0.1575(2) 0.031(2) Uani 1 1 d . . . H16A H 0.1769 -0.4361 -0.1392 0.037 Uiso 1 1 calc R . . H16B H 0.4511 -0.3876 -0.1397 0.037 Uiso 1 1 calc R . . C17 C 0.3822(14) -0.5465(9) -0.1818(3) 0.031(3) Uani 1 1 d . . . H17 H 0.4237 -0.6230 -0.1620 0.037 Uiso 1 1 calc R . . C18 C 0.5956(13) -0.5137(9) -0.2098(3) 0.033(2) Uani 1 1 d . . . H18A H 0.7426 -0.5226 -0.1928 0.039 Uiso 1 1 calc R . . H18B H 0.6034 -0.5852 -0.2320 0.039 Uiso 1 1 calc R . . C19 C 0.5987(14) -0.3735(10) -0.2306(3) 0.033(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 O1 0.032(3) 0.026(4) 0.031(4) 0.006(3) 0.010(3) 0.005(3) O2 0.035(3) 0.033(4) 0.036(4) 0.004(3) 0.013(3) 0.003(3) O3 0.038(3) 0.027(4) 0.048(5) -0.007(4) -0.003(3) 0.001(3) C1 0.034(5) 0.011(5) 0.032(6) 0.001(5) 0.000(5) 0.002(4) C2 0.021(4) 0.026(6) 0.023(5) -0.002(5) 0.004(4) 0.000(4) C3 0.040(5) 0.008(5) 0.046(7) -0.002(5) -0.005(5) -0.002(5) C4 0.050(6) 0.024(6) 0.025(6) 0.004(5) 0.012(5) 0.000(5) C5 0.024(4) 0.021(5) 0.023(5) -0.006(4) -0.001(4) 0.001(4) C6 0.034(5) 0.029(6) 0.026(6) -0.001(5) 0.001(4) 0.001(5) C7 0.031(5) 0.032(6) 0.028(6) 0.001(6) 0.007(5) 0.001(5) C8 0.044(5) 0.029(6) 0.033(6) 0.008(5) 0.006(5) -0.004(5) C9 0.050(5) 0.021(5) 0.018(5) -0.001(4) 0.008(5) 0.003(5) C10 0.021(4) 0.026(5) 0.017(5) 0.000(4) 0.001(4) -0.006(4) C11 0.044(5) 0.028(6) 0.028(6) 0.004(5) 0.003(5) 0.000(5) C12 0.078(6) 0.045(7) 0.024(6) -0.008(5) 0.006(6) 0.012(7) C13 0.026(4) 0.028(6) 0.028(6) -0.001(5) 0.004(4) -0.002(4) C14 0.041(5) 0.017(5) 0.029(6) 0.001(4) -0.003(5) 0.005(5) C15 0.025(4) 0.034(6) 0.015(5) -0.006(4) -0.005(5) 0.001(4) C16 0.037(5) 0.031(6) 0.023(6) 0.008(5) 0.017(5) 0.004(5) C17 0.030(5) 0.018(6) 0.044(7) -0.001(5) 0.002(5) 0.002(4) C18 0.030(4) 0.035(6) 0.034(6) -0.002(5) 0.000(4) 0.010(5) C19 0.021(4) 0.029(6) 0.050(7) -0.010(6) -0.013(5) 0.004(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 O1 C19 1.335(9) . ? O1 C15 1.483(9) . ? O2 C19 1.213(9) . ? O3 C17 1.414(9) . ? C1 C10 1.533(10) . ? C1 C2 1.539(11) . ? C1 C13 1.545(10) . ? C2 C3 1.515(11) . ? C2 C11 1.538(9) . ? C3 C4 1.311(10) . ? C4 C5 1.478(10) . ? C5 C10 1.520(10) . ? C5 C6 1.541(9) . ? C6 C7 1.520(11) . ? C7 C8 1.529(11) . ? C7 C12 1.537(10) . ? C8 C9 1.521(9) . ? C9 C10 1.536(10) . ? C13 C14 1.528(9) . ? C14 C15 1.541(9) . ? C15 C16 1.508(9) . ? C16 C17 1.521(10) . ? C17 C18 1.525(10) . ? C18 C19 1.507(11) . ? 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 C19 O1 C15 122.2(7) . . ? C10 C1 C2 109.4(7) . . ? C10 C1 C13 113.2(7) . . ? C2 C1 C13 113.5(7) . . ? C3 C2 C11 109.7(7) . . ? C3 C2 C1 110.5(7) . . ? C11 C2 C1 115.4(7) . . ? C4 C3 C2 124.4(9) . . ? C3 C4 C5 123.1(9) . . ? C4 C5 C10 111.5(7) . . ? C4 C5 C6 111.5(7) . . ? C10 C5 C6 111.6(7) . . ? C7 C6 C5 111.4(7) . . ? C6 C7 C8 110.5(7) . . ? C6 C7 C12 112.9(7) . . ? C8 C7 C12 112.0(7) . . ? C9 C8 C7 113.6(7) . . ? C8 C9 C10 111.4(7) . . ? C5 C10 C1 109.1(7) . . ? C5 C10 C9 110.0(6) . . ? C1 C10 C9 115.1(7) . . ? C14 C13 C1 111.1(7) . . ? C13 C14 C15 113.1(7) . . ? O1 C15 C16 111.2(6) . . ? O1 C15 C14 103.1(6) . . ? C16 C15 C14 114.2(6) . . ? C15 C16 C17 109.7(7) . . ? O3 C17 C16 106.9(6) . . ? O3 C17 C18 111.0(7) . . ? C16 C17 C18 108.7(7) . . ? C19 C18 C17 116.9(7) . . ? O2 C19 O1 118.4(9) . . ? O2 C19 C18 121.5(9) . . ? O1 C19 C18 119.9(8) . . ? 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 C10 C1 C2 C3 45.0(8) . . . . ? C13 C1 C2 C3 172.5(6) . . . . ? C10 C1 C2 C11 -80.1(8) . . . . ? C13 C1 C2 C11 47.4(9) . . . . ? C11 C2 C3 C4 114.2(8) . . . . ? C1 C2 C3 C4 -14.1(11) . . . . ? C2 C3 C4 C5 0.8(12) . . . . ? C3 C4 C5 C10 -19.5(11) . . . . ? C3 C4 C5 C6 -145.0(7) . . . . ? C4 C5 C6 C7 -177.2(7) . . . . ? C10 C5 C6 C7 57.3(8) . . . . ? C5 C6 C7 C8 -53.7(9) . . . . ? C5 C6 C7 C12 72.6(8) . . . . ? C6 C7 C8 C9 52.8(9) . . . . ? C12 C7 C8 C9 -73.9(9) . . . . ? C7 C8 C9 C10 -53.7(9) . . . . ? C4 C5 C10 C1 50.6(8) . . . . ? C6 C5 C10 C1 176.0(6) . . . . ? C4 C5 C10 C9 177.7(6) . . . . ? C6 C5 C10 C9 -56.9(9) . . . . ? C2 C1 C10 C5 -64.8(8) . . . . ? C13 C1 C10 C5 167.6(7) . . . . ? C2 C1 C10 C9 171.1(7) . . . . ? C13 C1 C10 C9 43.5(9) . . . . ? C8 C9 C10 C5 54.7(9) . . . . ? C8 C9 C10 C1 178.4(6) . . . . ? C10 C1 C13 C14 -174.4(6) . . . . ? C2 C1 C13 C14 60.2(9) . . . . ? C1 C13 C14 C15 175.2(6) . . . . ? C19 O1 C15 C16 33.7(9) . . . . ? C19 O1 C15 C14 156.6(7) . . . . ? C13 C14 C15 O1 169.8(6) . . . . ? C13 C14 C15 C16 -69.4(9) . . . . ? O1 C15 C16 C17 -57.1(9) . . . . ? C14 C15 C16 C17 -173.3(6) . . . . ? C15 C16 C17 O3 -60.5(9) . . . . ? C15 C16 C17 C18 59.4(9) . . . . ? O3 C17 C18 C19 78.6(10) . . . . ? C16 C17 C18 C19 -38.7(10) . . . . ? C15 O1 C19 O2 171.9(7) . . . . ? C15 O1 C19 C18 -12.6(11) . . . . ? C17 C18 C19 O2 -169.1(7) . . . . ? C17 C18 C19 O1 15.6(11) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.84 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.291 _refine_diff_density_min -0.310 _refine_diff_density_rms 0.101 #===END data_jcv0004 _database_code_CSD 191454 _audit_creation_method 'manual editing of SHELXL template' _chemical_formula_sum 'C19 H30 O4' _chemical_formula_weight 322.43 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 5.5318(11) _cell_length_b 9.7123(19) _cell_length_c 32.163(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1728.0(6) _cell_formula_units_Z 4 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 4294 _cell_measurement_theta_min 2.450 _cell_measurement_theta_max 26.186 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.39 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.239 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 704 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9587 _exptl_absorpt_correction_T_max 0.9966 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1997)' _diffrn_ambient_temperature 193(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker PLATFORM diffractometer/SMART 1000 CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8.192 _diffrn_standards_number 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 9765 _diffrn_reflns_av_R_equivalents 0.0680 _diffrn_reflns_av_sigmaI/netI 0.0747 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -39 _diffrn_reflns_limit_l_max 40 _diffrn_reflns_theta_min 2.19 _diffrn_reflns_theta_max 26.39 _reflns_number_total 3482 _reflns_number_gt 2478 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART (Bruker, 1997)' _computing_cell_refinement 'Bruker SAINT (Bruker, 1997)' _computing_data_reduction 'Bruker SAINT (Bruker, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL (Sheldrick, 1997)' _computing_publication_material 'Bruker SHELXTL (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0453P)^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 constr _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 3482 _refine_ls_number_parameters 209 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0885 _refine_ls_R_factor_gt 0.0538 _refine_ls_wR_factor_ref 0.1044 _refine_ls_wR_factor_gt 0.0944 _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_restrained_S_all 1.016 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_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_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 0.4497(3) 0.20875(16) 0.28165(5) 0.0292(4) Uani 1 1 d . . . O2 O 0.7398(3) 0.13988(17) 0.24149(5) 0.0329(4) Uani 1 1 d . . . O3 O 0.1860(3) -0.09667(17) 0.29272(6) 0.0351(5) Uani 1 1 d . . . H3O H 0.2215 -0.1661 0.2784 0.053 Uiso 1 1 calc R . . O4 O 0.1227(3) 0.75533(19) 0.40438(5) 0.0413(5) Uani 1 1 d . . . C1 C 0.6002(4) 0.1106(2) 0.26875(7) 0.0248(6) Uani 1 1 d . . . C2 C 0.6028(4) -0.0261(2) 0.28981(8) 0.0298(6) Uani 1 1 d . . . H2A H 0.7508 -0.0319 0.3070 0.036 Uiso 1 1 calc R . . H2B H 0.6144 -0.0984 0.2682 0.036 Uiso 1 1 calc R . . C3 C 0.3879(4) -0.0579(2) 0.31711(7) 0.0269(6) Uani 1 1 d . . . H3 H 0.4297 -0.1336 0.3369 0.032 Uiso 1 1 calc R . . C4 C 0.3168(4) 0.0688(2) 0.34088(7) 0.0293(6) Uani 1 1 d . . . H4A H 0.4522 0.0980 0.3590 0.035 Uiso 1 1 calc R . . H4B H 0.1760 0.0479 0.3588 0.035 Uiso 1 1 calc R . . C5 C 0.2533(4) 0.1835(2) 0.31131(7) 0.0255(6) Uani 1 1 d . . . H5 H 0.1045 0.1572 0.2955 0.031 Uiso 1 1 calc R . . C6 C 0.2133(4) 0.3230(2) 0.33121(7) 0.0303(6) Uani 1 1 d . . . H6A H 0.1958 0.3926 0.3089 0.036 Uiso 1 1 calc R . . H6B H 0.3587 0.3472 0.3476 0.036 Uiso 1 1 calc R . . C7 C -0.0067(4) 0.3312(2) 0.35950(7) 0.0258(6) Uani 1 1 d . . . H7A H 0.0029 0.2574 0.3807 0.031 Uiso 1 1 calc R . . H7B H -0.1548 0.3159 0.3428 0.031 Uiso 1 1 calc R . . C8 C -0.0239(4) 0.4710(2) 0.38132(7) 0.0210(5) Uani 1 1 d . . . H8 H 0.1298 0.4821 0.3974 0.025 Uiso 1 1 calc R . . C9 C -0.0336(4) 0.5926(2) 0.35056(7) 0.0239(5) Uani 1 1 d . . . H9 H 0.1238 0.5939 0.3353 0.029 Uiso 1 1 calc R . . C10 C -0.0550(4) 0.7273(3) 0.37302(7) 0.0295(6) Uani 1 1 d . . . H10 H -0.1027 0.8078 0.3554 0.035 Uiso 1 1 calc R . . C11 C -0.1272(5) 0.7351(3) 0.41639(8) 0.0318(6) Uani 1 1 d . . . H11 H -0.2175 0.8200 0.4247 0.038 Uiso 1 1 calc R . . C12 C -0.1822(4) 0.6077(2) 0.44125(7) 0.0257(6) Uani 1 1 d . . . H12 H -0.0350 0.5863 0.4581 0.031 Uiso 1 1 calc R . . C13 C -0.3889(5) 0.6310(3) 0.47166(8) 0.0320(6) Uani 1 1 d . . . H13A H -0.5370 0.6546 0.4559 0.038 Uiso 1 1 calc R . . H13B H -0.3491 0.7101 0.4898 0.038 Uiso 1 1 calc R . . C14 C -0.4385(5) 0.5051(3) 0.49858(8) 0.0339(7) Uani 1 1 d . . . H14 H -0.5939 0.5218 0.5136 0.041 Uiso 1 1 calc R . . C15 C -0.4748(5) 0.3795(3) 0.47093(8) 0.0347(6) Uani 1 1 d . . . H15A H -0.4889 0.2968 0.4888 0.042 Uiso 1 1 calc R . . H15B H -0.6290 0.3900 0.4556 0.042 Uiso 1 1 calc R . . C16 C -0.2725(4) 0.3568(2) 0.43978(7) 0.0283(6) Uani 1 1 d . . . H16A H -0.1219 0.3336 0.4549 0.034 Uiso 1 1 calc R . . H16B H -0.3141 0.2779 0.4217 0.034 Uiso 1 1 calc R . . C17 C -0.2294(4) 0.4832(2) 0.41306(7) 0.0214(5) Uani 1 1 d . . . H17 H -0.3817 0.5018 0.3973 0.026 Uiso 1 1 calc R . . C18 C -0.2325(4) 0.5824(3) 0.31812(7) 0.0337(6) Uani 1 1 d . . . H18A H -0.2268 0.6635 0.3000 0.040 Uiso 1 1 calc R . . H18B H -0.3900 0.5782 0.3320 0.040 Uiso 1 1 calc R . . H18C H -0.2089 0.4991 0.3014 0.040 Uiso 1 1 calc R . . C19 C -0.2438(6) 0.4817(3) 0.53118(8) 0.0444(7) Uani 1 1 d . . . H19A H -0.2287 0.5640 0.5486 0.053 Uiso 1 1 calc R . . H19B H -0.0892 0.4633 0.5174 0.053 Uiso 1 1 calc R . . H19C H -0.2880 0.4027 0.5486 0.053 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 0.0312(10) 0.0189(9) 0.0374(10) 0.0023(8) 0.0118(8) 0.0057(7) O2 0.0301(10) 0.0293(10) 0.0392(10) 0.0035(8) 0.0111(9) 0.0017(8) O3 0.0279(10) 0.0217(10) 0.0557(12) -0.0098(9) 0.0018(9) 0.0000(8) O4 0.0427(11) 0.0353(12) 0.0457(11) -0.0067(10) -0.0007(10) -0.0151(9) C1 0.0204(12) 0.0242(14) 0.0297(13) -0.0012(12) 0.0007(12) 0.0010(11) C2 0.0265(13) 0.0223(14) 0.0406(15) 0.0016(13) 0.0013(12) 0.0035(11) C3 0.0274(13) 0.0189(14) 0.0345(14) 0.0042(12) 0.0006(12) 0.0011(10) C4 0.0338(15) 0.0254(15) 0.0286(13) 0.0011(12) 0.0042(12) -0.0015(11) C5 0.0243(13) 0.0232(14) 0.0290(13) -0.0044(11) 0.0068(11) 0.0008(11) C6 0.0348(15) 0.0201(14) 0.0361(15) -0.0025(12) 0.0055(12) 0.0013(11) C7 0.0311(14) 0.0180(13) 0.0282(13) -0.0019(11) 0.0060(11) 0.0020(11) C8 0.0198(12) 0.0185(13) 0.0247(12) -0.0022(11) 0.0002(10) 0.0006(10) C9 0.0240(13) 0.0208(13) 0.0270(13) 0.0008(11) 0.0045(11) -0.0018(11) C10 0.0341(15) 0.0200(14) 0.0345(14) 0.0017(12) -0.0004(12) -0.0026(12) C11 0.0356(15) 0.0179(14) 0.0418(16) -0.0060(12) 0.0003(13) 0.0029(11) C12 0.0262(13) 0.0207(14) 0.0302(13) -0.0012(12) -0.0015(11) 0.0007(11) C13 0.0382(15) 0.0251(15) 0.0327(14) -0.0059(12) 0.0040(13) 0.0049(12) C14 0.0386(16) 0.0320(16) 0.0312(14) -0.0014(12) 0.0114(13) 0.0030(12) C15 0.0400(16) 0.0305(16) 0.0336(14) 0.0018(12) 0.0073(13) -0.0047(13) C16 0.0364(15) 0.0197(14) 0.0287(13) -0.0018(11) 0.0050(12) -0.0024(12) C17 0.0235(13) 0.0177(13) 0.0229(12) -0.0029(10) -0.0017(11) -0.0003(10) C18 0.0366(15) 0.0300(16) 0.0345(14) 0.0028(12) -0.0018(13) 0.0013(12) C19 0.071(2) 0.0304(17) 0.0319(15) -0.0018(13) 0.0040(16) 0.0045(15) _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 1.332(3) . ? O1 C5 1.466(3) . ? O2 C1 1.203(3) . ? O3 C3 1.416(3) . ? O4 C10 1.434(3) . ? O4 C11 1.449(3) . ? C1 C2 1.490(3) . ? C2 C3 1.510(3) . ? C3 C4 1.501(3) . ? C4 C5 1.506(3) . ? C5 C6 1.515(3) . ? C6 C7 1.521(3) . ? C7 C8 1.531(3) . ? C8 C17 1.532(3) . ? C8 C9 1.541(3) . ? C9 C10 1.500(3) . ? C9 C18 1.519(3) . ? C10 C11 1.453(3) . ? C11 C12 1.504(3) . ? C12 C13 1.522(3) . ? C12 C17 1.534(3) . ? C13 C14 1.524(3) . ? C14 C19 1.520(4) . ? C14 C15 1.523(3) . ? C15 C16 1.518(3) . ? C16 C17 1.517(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 C5 123.10(18) . . ? C10 O4 C11 60.52(15) . . ? O2 C1 O1 117.4(2) . . ? O2 C1 C2 122.4(2) . . ? O1 C1 C2 120.1(2) . . ? C1 C2 C3 116.0(2) . . ? O3 C3 C4 107.07(19) . . ? O3 C3 C2 110.71(19) . . ? C4 C3 C2 109.6(2) . . ? C3 C4 C5 110.2(2) . . ? O1 C5 C4 111.20(19) . . ? O1 C5 C6 103.52(18) . . ? C4 C5 C6 115.4(2) . . ? C5 C6 C7 114.6(2) . . ? C6 C7 C8 111.74(19) . . ? C7 C8 C17 114.82(18) . . ? C7 C8 C9 112.77(18) . . ? C17 C8 C9 110.03(19) . . ? C10 C9 C18 109.3(2) . . ? C10 C9 C8 111.22(18) . . ? C18 C9 C8 114.6(2) . . ? O4 C10 C11 60.23(15) . . ? O4 C10 C9 116.8(2) . . ? C11 C10 C9 122.0(2) . . ? O4 C11 C10 59.25(15) . . ? O4 C11 C12 116.5(2) . . ? C10 C11 C12 121.6(2) . . ? C11 C12 C13 111.8(2) . . ? C11 C12 C17 111.62(19) . . ? C13 C12 C17 111.66(19) . . ? C12 C13 C14 112.4(2) . . ? C19 C14 C15 112.1(2) . . ? C19 C14 C13 112.6(2) . . ? C15 C14 C13 109.6(2) . . ? C16 C15 C14 113.9(2) . . ? C17 C16 C15 111.8(2) . . ? C16 C17 C8 115.56(19) . . ? C16 C17 C12 109.26(18) . . ? C8 C17 C12 109.16(18) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 O1 C1 O2 173.14(19) . . . . ? C5 O1 C1 C2 -10.9(3) . . . . ? O2 C1 C2 C3 -168.3(2) . . . . ? O1 C1 C2 C3 16.0(3) . . . . ? C1 C2 C3 O3 77.8(3) . . . . ? C1 C2 C3 C4 -40.1(3) . . . . ? O3 C3 C4 C5 -60.8(3) . . . . ? C2 C3 C4 C5 59.4(3) . . . . ? C1 O1 C5 C4 30.1(3) . . . . ? C1 O1 C5 C6 154.6(2) . . . . ? C3 C4 C5 O1 -54.1(3) . . . . ? C3 C4 C5 C6 -171.5(2) . . . . ? O1 C5 C6 C7 172.04(18) . . . . ? C4 C5 C6 C7 -66.2(3) . . . . ? C5 C6 C7 C8 175.2(2) . . . . ? C6 C7 C8 C17 -175.29(18) . . . . ? C6 C7 C8 C9 57.6(3) . . . . ? C7 C8 C9 C10 178.94(19) . . . . ? C17 C8 C9 C10 49.3(2) . . . . ? C7 C8 C9 C18 54.4(3) . . . . ? C17 C8 C9 C18 -75.3(2) . . . . ? C11 O4 C10 C9 -113.2(2) . . . . ? C18 C9 C10 O4 -178.79(19) . . . . ? C8 C9 C10 O4 53.7(3) . . . . ? C18 C9 C10 C11 111.1(3) . . . . ? C8 C9 C10 C11 -16.4(3) . . . . ? C10 O4 C11 C12 112.6(2) . . . . ? C9 C10 C11 O4 104.7(2) . . . . ? O4 C10 C11 C12 -104.1(2) . . . . ? C9 C10 C11 C12 0.6(4) . . . . ? O4 C11 C12 C13 147.7(2) . . . . ? C10 C11 C12 C13 -143.6(2) . . . . ? O4 C11 C12 C17 -86.4(2) . . . . ? C10 C11 C12 C17 -17.7(3) . . . . ? C11 C12 C13 C14 -177.2(2) . . . . ? C17 C12 C13 C14 57.0(3) . . . . ? C12 C13 C14 C19 72.4(3) . . . . ? C12 C13 C14 C15 -53.1(3) . . . . ? C19 C14 C15 C16 -73.4(3) . . . . ? C13 C14 C15 C16 52.4(3) . . . . ? C14 C15 C16 C17 -54.9(3) . . . . ? C15 C16 C17 C8 178.60(19) . . . . ? C15 C16 C17 C12 55.1(3) . . . . ? C7 C8 C17 C16 39.8(3) . . . . ? C9 C8 C17 C16 168.30(19) . . . . ? C7 C8 C17 C12 163.40(19) . . . . ? C9 C8 C17 C12 -68.1(2) . . . . ? C11 C12 C17 C16 177.5(2) . . . . ? C13 C12 C17 C16 -56.6(3) . . . . ? C11 C12 C17 C8 50.2(2) . . . . ? C13 C12 C17 C8 176.20(18) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 26.39 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.217 _refine_diff_density_min -0.161 _refine_diff_density_rms 0.042 #===END