# Perkin Transactions I © The Royal Society of Chemistry, 1999 # CCDC Number: 207/343 # Maunscript submitted to Perkin Trans I: 9/03961I. # Title: 'Radical-chain reductive alkylation of # electron-rich alkenes mediated by silanes in the # presence of thiols as polarity-reversal catalysts.' # Authors: Hai-Shan Dang, Kyoung-Mahn Kim, # Brian P. Roberts, and Mark R.J. Elsegood. # # This file contains two CIFs. data_(S)-11bg _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H28 O3' _chemical_formula_weight 364.46 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 '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' 0.0492 0.0322 '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) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.8331(10) _cell_length_b 10.3392(10) _cell_length_c 10.5216(12) _cell_angle_alpha 90.00 _cell_angle_beta 99.957(12) _cell_angle_gamma 90.00 _cell_volume 1053.58(19) _cell_formula_units_Z 2 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 43 _cell_measurement_theta_min 22.68 _cell_measurement_theta_max 24.98 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.65 _exptl_crystal_size_mid 0.63 _exptl_crystal_size_min 0.62 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.149 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 392 _exptl_absorpt_coefficient_mu 0.586 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.525 _exptl_absorpt_correction_T_max 0.664 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Stoe-Siemens diffractometer' _diffrn_measurement_method '\w/\q scans with on-line profile fitting' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 5 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 0.5 _diffrn_reflns_number 3660 _diffrn_reflns_av_R_equivalents 0.0436 _diffrn_reflns_av_sigmaI/netI 0.0166 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 4.27 _diffrn_reflns_theta_max 67.54 _reflns_number_total 3467 _reflns_number_gt 3435 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Stoe DIF4' _computing_cell_refinement 'Stoe DIF4' _computing_data_reduction 'local programs' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'SHELXTL and local programs' _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. Two-fold disorder in t-Bu group modelled with restraints on geometry and adp's. Approx 51:49% ratio of the two components. ; _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^)+(0.0822P)^2^+0.1938P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0182(15) _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 0.1(3) _refine_ls_number_reflns 3467 _refine_ls_number_parameters 279 _refine_ls_number_restraints 79 _refine_ls_R_factor_all 0.0453 _refine_ls_R_factor_gt 0.0450 _refine_ls_wR_factor_ref 0.1269 _refine_ls_wR_factor_gt 0.1266 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.074 _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 0.53258(19) 0.00762(17) 0.21211(17) 0.0336(4) Uani 1 1 d . . . C2 C 0.5998(2) -0.07622(18) 0.32671(18) 0.0392(4) Uani 1 1 d . . . H2A H 0.5815 -0.1687 0.3063 0.047 Uiso 1 1 calc R . . H2B H 0.7010 -0.0627 0.3427 0.047 Uiso 1 1 calc R . . C3 C 0.5414(3) -0.04004(19) 0.4466(2) 0.0490(5) Uani 1 1 d . . . H3A H 0.4488 -0.0797 0.4401 0.059 Uiso 1 1 calc R . . H3B H 0.6011 -0.0785 0.5226 0.059 Uiso 1 1 calc R . . C4 C 0.5286(3) 0.1018(2) 0.4702(2) 0.0501(5) Uani 1 1 d . . . O1 O 0.52878(16) 0.18560(12) 0.37229(12) 0.0431(3) Uani 1 1 d . . . C5 C 0.56739(19) 0.15025(17) 0.24893(16) 0.0338(4) Uani 1 1 d . . . H5 H 0.5117 0.2055 0.1812 0.041 Uiso 1 1 calc R . . O2 O 0.5113(3) 0.14521(18) 0.57118(17) 0.0867(7) Uani 1 1 d . . . C6 C 0.7185(2) 0.18840(19) 0.25610(18) 0.0384(4) Uani 1 1 d . . . H6A H 0.7764 0.1372 0.3245 0.046 Uiso 1 1 calc R . . H6B H 0.7478 0.1678 0.1730 0.046 Uiso 1 1 calc R . . C7 C 0.7411(2) 0.3321(2) 0.2850(2) 0.0466(5) Uani 1 1 d . . . H7A H 0.6923 0.3824 0.2109 0.056 Uiso 1 1 calc R . . H7B H 0.6992 0.3543 0.3612 0.056 Uiso 1 1 calc R . . C8 C 0.8902(2) 0.3724(2) 0.3105(2) 0.0449(5) Uani 1 1 d . A . O3 O 0.9800(2) 0.2977(2) 0.2982(3) 0.1037(10) Uani 1 1 d . . . C9 C 0.9255(2) 0.5108(2) 0.3488(3) 0.0578(6) Uani 1 1 d DU . . C10 C 0.9218(8) 0.5699(7) 0.2016(7) 0.087(2) Uani 0.516(7) 1 d PDU A 1 H10A H 0.8287 0.5600 0.1513 0.131 Uiso 0.516(7) 1 calc PR A 1 H10B H 0.9879 0.5228 0.1591 0.131 Uiso 0.516(7) 1 calc PR A 1 H10C H 0.9465 0.6618 0.2074 0.131 Uiso 0.516(7) 1 calc PR A 1 C11 C 1.0673(10) 0.5319(17) 0.4144(13) 0.107(5) Uani 0.516(7) 1 d PDU A 1 H11A H 1.0914 0.6234 0.4079 0.160 Uiso 0.516(7) 1 calc PR A 1 H11B H 1.1303 0.4787 0.3738 0.160 Uiso 0.516(7) 1 calc PR A 1 H11C H 1.0754 0.5078 0.5055 0.160 Uiso 0.516(7) 1 calc PR A 1 C12 C 0.8153(6) 0.5879(6) 0.3963(8) 0.076(2) Uani 0.516(7) 1 d PDU A 1 H12A H 0.8418 0.6793 0.4017 0.114 Uiso 0.516(7) 1 calc PR A 1 H12B H 0.8043 0.5568 0.4819 0.114 Uiso 0.516(7) 1 calc PR A 1 H12C H 0.7279 0.5779 0.3363 0.114 Uiso 0.516(7) 1 calc PR A 1 C10X C 0.8346(8) 0.6102(6) 0.2883(11) 0.099(3) Uani 0.484(7) 1 d PDU A 2 H10D H 0.8751 0.6952 0.3127 0.148 Uiso 0.484(7) 1 calc PR A 2 H10E H 0.7451 0.6031 0.3167 0.148 Uiso 0.484(7) 1 calc PR A 2 H10F H 0.8218 0.6003 0.1944 0.148 Uiso 0.484(7) 1 calc PR A 2 C11X C 1.0762(9) 0.5369(11) 0.3620(13) 0.080(3) Uani 0.484(7) 1 d PDU A 2 H11D H 1.1010 0.5457 0.2761 0.121 Uiso 0.484(7) 1 calc PR A 2 H11E H 1.1281 0.4651 0.4079 0.121 Uiso 0.484(7) 1 calc PR A 2 H11F H 1.0986 0.6172 0.4106 0.121 Uiso 0.484(7) 1 calc PR A 2 C12X C 0.9070(9) 0.5051(10) 0.5014(7) 0.106(3) Uani 0.484(7) 1 d PDU A 2 H12D H 0.9376 0.5871 0.5436 0.158 Uiso 0.484(7) 1 calc PR A 2 H12E H 0.9628 0.4341 0.5448 0.158 Uiso 0.484(7) 1 calc PR A 2 H12F H 0.8097 0.4906 0.5067 0.158 Uiso 0.484(7) 1 calc PR A 2 C13 C 0.58760(19) -0.02248(18) 0.08798(17) 0.0358(4) Uani 1 1 d . . . C14 C 0.5314(3) 0.0424(2) -0.02511(19) 0.0495(5) Uani 1 1 d . . . H14 H 0.4599 0.1040 -0.0240 0.059 Uiso 1 1 calc R . . C15 C 0.5795(3) 0.0177(3) -0.1398(2) 0.0655(8) Uani 1 1 d . . . H15 H 0.5414 0.0631 -0.2162 0.079 Uiso 1 1 calc R . . C16 C 0.6823(3) -0.0725(3) -0.1428(3) 0.0704(8) Uani 1 1 d . . . H16 H 0.7153 -0.0892 -0.2209 0.084 Uiso 1 1 calc R . . C17 C 0.7365(3) -0.1379(3) -0.0322(3) 0.0660(7) Uani 1 1 d . . . H17 H 0.8061 -0.2011 -0.0345 0.079 Uiso 1 1 calc R . . C18 C 0.6908(2) -0.1128(2) 0.0826(2) 0.0485(5) Uani 1 1 d . . . H18 H 0.7306 -0.1580 0.1586 0.058 Uiso 1 1 calc R . . C19 C 0.3759(2) -0.0188(2) 0.18653(19) 0.0414(4) Uani 1 1 d . . . C20 C 0.3305(2) -0.1398(2) 0.1384(3) 0.0571(6) Uani 1 1 d . . . H20 H 0.3964 -0.2018 0.1217 0.069 Uiso 1 1 calc R . . C21 C 0.1927(3) -0.1717(3) 0.1147(4) 0.0817(9) Uani 1 1 d . . . H21 H 0.1645 -0.2549 0.0821 0.098 Uiso 1 1 calc R . . C22 C 0.0956(3) -0.0832(4) 0.1380(4) 0.0892(11) Uani 1 1 d . . . H22 H 0.0003 -0.1049 0.1218 0.107 Uiso 1 1 calc R . . C23 C 0.1377(3) 0.0372(3) 0.1852(3) 0.0745(8) Uani 1 1 d . . . H23 H 0.0709 0.0987 0.2011 0.089 Uiso 1 1 calc R . . C24 C 0.2765(2) 0.0696(2) 0.2095(2) 0.0519(5) Uani 1 1 d . . . H24 H 0.3040 0.1530 0.2422 0.062 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 0.0372(9) 0.0268(9) 0.0366(8) 0.0014(7) 0.0060(7) 0.0021(7) C2 0.0516(11) 0.0263(8) 0.0395(10) 0.0037(7) 0.0068(8) 0.0037(8) C3 0.0751(15) 0.0336(10) 0.0400(9) 0.0062(8) 0.0151(10) 0.0031(10) C4 0.0722(15) 0.0403(11) 0.0408(11) -0.0009(8) 0.0181(10) 0.0006(10) O1 0.0626(9) 0.0275(7) 0.0419(7) -0.0030(5) 0.0167(6) 0.0013(6) C5 0.0398(10) 0.0273(9) 0.0341(8) 0.0017(6) 0.0056(7) 0.0026(7) O2 0.170(2) 0.0516(10) 0.0492(9) -0.0037(8) 0.0482(12) 0.0114(13) C6 0.0406(10) 0.0299(9) 0.0433(9) 0.0003(7) 0.0034(7) 0.0010(8) C7 0.0404(11) 0.0308(10) 0.0667(13) -0.0042(9) 0.0043(9) 0.0004(8) C8 0.0398(11) 0.0372(11) 0.0564(11) -0.0005(9) 0.0051(9) 0.0044(9) O3 0.0497(11) 0.0517(11) 0.207(3) -0.0358(14) 0.0143(14) 0.0056(9) C9 0.0418(12) 0.0419(12) 0.0908(17) -0.0146(11) 0.0148(11) -0.0067(10) C10 0.100(5) 0.065(4) 0.098(4) 0.019(3) 0.018(3) -0.022(4) C11 0.060(4) 0.108(8) 0.134(9) -0.063(7) -0.034(6) 0.014(5) C12 0.064(3) 0.044(3) 0.125(6) -0.034(3) 0.029(4) -0.011(2) C10X 0.064(4) 0.042(3) 0.183(9) -0.004(4) -0.001(5) 0.004(3) C11X 0.048(3) 0.051(4) 0.143(10) -0.032(6) 0.018(5) -0.021(3) C12X 0.107(6) 0.127(7) 0.090(4) -0.059(4) 0.037(4) -0.054(5) C13 0.0366(9) 0.0334(9) 0.0371(9) -0.0052(7) 0.0051(7) -0.0111(8) C14 0.0647(14) 0.0432(11) 0.0394(10) 0.0011(8) 0.0057(9) -0.0133(10) C15 0.095(2) 0.0634(15) 0.0380(10) -0.0031(10) 0.0104(11) -0.0371(15) C16 0.0780(18) 0.088(2) 0.0516(14) -0.0310(13) 0.0290(13) -0.0365(16) C17 0.0506(13) 0.0849(19) 0.0649(15) -0.0397(14) 0.0164(11) -0.0112(13) C18 0.0424(11) 0.0541(13) 0.0483(11) -0.0176(9) 0.0056(9) -0.0014(9) C19 0.0389(10) 0.0373(10) 0.0485(10) 0.0021(8) 0.0089(8) -0.0017(8) C20 0.0463(12) 0.0454(12) 0.0813(16) -0.0118(11) 0.0157(11) -0.0071(10) C21 0.0592(16) 0.0727(19) 0.115(2) -0.0302(18) 0.0209(16) -0.0228(15) C22 0.0415(14) 0.096(2) 0.131(3) -0.022(2) 0.0172(16) -0.0177(15) C23 0.0440(13) 0.0710(18) 0.110(2) -0.0047(17) 0.0180(14) 0.0091(13) C24 0.0438(12) 0.0460(12) 0.0673(14) 0.0005(10) 0.0131(10) 0.0031(10) _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 C13 1.530(2) . ? C1 C2 1.538(2) . ? C1 C19 1.542(3) . ? C1 C5 1.548(2) . ? C2 C3 1.521(3) . ? C3 C4 1.496(3) . ? C4 O2 1.192(3) . ? C4 O1 1.347(3) . ? O1 C5 1.460(2) . ? C5 C6 1.527(3) . ? C6 C7 1.525(3) . ? C7 C8 1.503(3) . ? C8 O3 1.197(3) . ? C8 C9 1.510(3) . ? C9 C10X 1.437(7) . ? C9 C11 1.462(9) . ? C9 C11X 1.489(8) . ? C9 C12 1.499(6) . ? C9 C12X 1.648(7) . ? C9 C10 1.660(7) . ? C13 C18 1.388(3) . ? C13 C14 1.394(3) . ? C14 C15 1.394(3) . ? C15 C16 1.379(5) . ? C16 C17 1.371(5) . ? C17 C18 1.384(3) . ? C19 C24 1.389(3) . ? C19 C20 1.393(3) . ? C20 C21 1.375(4) . ? C21 C22 1.374(5) . ? C22 C23 1.377(5) . ? C23 C24 1.386(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C13 C1 C2 112.77(15) . . ? C13 C1 C19 107.77(15) . . ? C2 C1 C19 108.54(15) . . ? C13 C1 C5 108.18(13) . . ? C2 C1 C5 107.10(14) . . ? C19 C1 C5 112.55(15) . . ? C3 C2 C1 109.81(16) . . ? C4 C3 C2 115.69(17) . . ? O2 C4 O1 117.3(2) . . ? O2 C4 C3 123.1(2) . . ? O1 C4 C3 119.52(17) . . ? C4 O1 C5 123.63(15) . . ? O1 C5 C6 106.97(14) . . ? O1 C5 C1 112.38(13) . . ? C6 C5 C1 115.45(15) . . ? C7 C6 C5 111.65(16) . . ? C8 C7 C6 114.21(17) . . ? O3 C8 C7 121.1(2) . . ? O3 C8 C9 120.0(2) . . ? C7 C8 C9 118.85(17) . . ? C10X C9 C11 124.9(8) . . ? C10X C9 C11X 116.3(6) . . ? C11 C9 C11X 22.5(8) . . ? C10X C9 C12 48.5(5) . . ? C11 C9 C12 116.7(6) . . ? C11X C9 C12 129.6(5) . . ? C10X C9 C8 117.6(4) . . ? C11 C9 C8 115.1(7) . . ? C11X C9 C8 112.1(5) . . ? C12 C9 C8 116.5(3) . . ? C10X C9 C12X 107.0(6) . . ? C11 C9 C12X 78.6(6) . . ? C11X C9 C12X 101.0(6) . . ? C12 C9 C12X 59.1(5) . . ? C8 C9 C12X 99.6(3) . . ? C10X C9 C10 54.0(5) . . ? C11 C9 C10 104.5(7) . . ? C11X C9 C10 83.2(6) . . ? C12 C9 C10 102.4(5) . . ? C8 C9 C10 97.6(3) . . ? C12X C9 C10 159.1(5) . . ? C18 C13 C14 118.30(19) . . ? C18 C13 C1 122.74(17) . . ? C14 C13 C1 118.96(18) . . ? C15 C14 C13 120.4(2) . . ? C16 C15 C14 120.3(2) . . ? C17 C16 C15 119.5(2) . . ? C16 C17 C18 120.8(3) . . ? C17 C18 C13 120.7(2) . . ? C24 C19 C20 117.6(2) . . ? C24 C19 C1 124.35(19) . . ? C20 C19 C1 118.03(18) . . ? C21 C20 C19 121.7(2) . . ? C22 C21 C20 120.1(3) . . ? C21 C22 C23 119.4(3) . . ? C22 C23 C24 120.7(3) . . ? C23 C24 C19 120.5(2) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 67.54 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.215 _refine_diff_density_min -0.129 _refine_diff_density_rms 0.027 #===END data_(S)-11ai _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H28 O8' _chemical_formula_weight 372.40 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 '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' 0.0492 0.0322 '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) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.0392(8) _cell_length_b 7.6254(6) _cell_length_c 13.2278(11) _cell_angle_alpha 90.00 _cell_angle_beta 107.559(7) _cell_angle_gamma 90.00 _cell_volume 965.44(13) _cell_formula_units_Z 2 _cell_measurement_temperature 160(2) _cell_measurement_reflns_used 42 _cell_measurement_theta_min 21.45 _cell_measurement_theta_max 24.90 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.281 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 400 _exptl_absorpt_coefficient_mu 0.843 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.708 _exptl_absorpt_correction_T_max 0.891 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 160(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Bede Scientific Microsource tube' _diffrn_radiation_monochromator '8 micron nickel filter' _diffrn_measurement_device_type 'Stoe-Siemens diffractometer' _diffrn_measurement_method '\w/\q scans with on-line profile fitting' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 5 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 2 _diffrn_reflns_number 3630 _diffrn_reflns_av_R_equivalents 0.0267 _diffrn_reflns_av_sigmaI/netI 0.0243 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.50 _diffrn_reflns_theta_max 67.60 _reflns_number_total 2956 _reflns_number_gt 2898 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Stoe DIF4' _computing_cell_refinement 'Stoe DIF4' _computing_data_reduction 'local programs' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'SHELXTL and local programs' _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^)+(0.0609P)^2^+0.3260P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary 'all non-H atoms found by direct methods' _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0249(18) _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 0.1(2) _refine_ls_number_reflns 2956 _refine_ls_number_parameters 241 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0420 _refine_ls_R_factor_gt 0.0409 _refine_ls_wR_factor_ref 0.1101 _refine_ls_wR_factor_gt 0.1086 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _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 0.69786(18) 0.1240(2) 0.83343(13) 0.0359(4) Uani 1 1 d . . . C1 C 0.7975(2) 0.2698(3) 0.85474(17) 0.0277(4) Uani 1 1 d . . . H1 H 0.8925 0.2232 0.8931 0.033 Uiso 1 1 calc R . . C2 C 0.7596(3) 0.4109(3) 0.92340(19) 0.0354(5) Uani 1 1 d . . . C3 C 0.7641(3) 0.3180(4) 1.0271(2) 0.0490(7) Uani 1 1 d . . . H3A H 0.8620 0.2853 1.0647 0.059 Uiso 1 1 calc R . . H3B H 0.7330 0.4011 1.0729 0.059 Uiso 1 1 calc R . . C4 C 0.6761(4) 0.1584(4) 1.0123(2) 0.0612(9) Uani 1 1 d . . . H4A H 0.5855 0.1920 1.0220 0.073 Uiso 1 1 calc R . . H4B H 0.7216 0.0755 1.0700 0.073 Uiso 1 1 calc R . . O2 O 0.5701(2) -0.0632(3) 0.88821(18) 0.0581(6) Uani 1 1 d . . . C6 C 0.6159(3) 0.4905(3) 0.8698(2) 0.0428(6) Uani 1 1 d . . . H6A H 0.6152 0.5432 0.8020 0.064 Uiso 1 1 calc R . . H6B H 0.5958 0.5809 0.9158 0.064 Uiso 1 1 calc R . . H6C H 0.5446 0.3985 0.8571 0.064 Uiso 1 1 calc R . . C7 C 0.8702(3) 0.5549(4) 0.9483(2) 0.0537(7) Uani 1 1 d . . . H7A H 0.9629 0.5023 0.9780 0.081 Uiso 1 1 calc R . . H7B H 0.8523 0.6366 0.9999 0.081 Uiso 1 1 calc R . . H7C H 0.8665 0.6183 0.8831 0.081 Uiso 1 1 calc R . . C8 C 0.7975(2) 0.3316(3) 0.74499(17) 0.0272(4) Uani 1 1 d . . . H8A H 0.8302 0.4547 0.7505 0.033 Uiso 1 1 calc R . . H8B H 0.7001 0.3300 0.6974 0.033 Uiso 1 1 calc R . . C9 C 0.8892(2) 0.2217(3) 0.69337(16) 0.0257(4) Uani 1 1 d . . . C10 C 1.0446(2) 0.2513(3) 0.75317(16) 0.0290(4) Uani 1 1 d . . . O3 O 1.08536(19) 0.3492(3) 0.82630(16) 0.0570(6) Uani 1 1 d . . . O4 O 1.12646(19) 0.1614(3) 0.7123(2) 0.0651(7) Uani 1 1 d . . . C11 C 1.2769(3) 0.1815(5) 0.7564(3) 0.0589(8) Uani 1 1 d . . . H11A H 1.3181 0.0768 0.7985 0.071 Uiso 1 1 calc R . . H11B H 1.2992 0.2857 0.8032 0.071 Uiso 1 1 calc R . . C12 C 1.3337(3) 0.2030(5) 0.6658(3) 0.0603(8) Uani 1 1 d . . . H12A H 1.3013 0.1062 0.6157 0.090 Uiso 1 1 calc R . . H12B H 1.4361 0.2025 0.6919 0.090 Uiso 1 1 calc R . . H12C H 1.3013 0.3146 0.6301 0.090 Uiso 1 1 calc R . . C13 C 0.8668(2) 0.2910(3) 0.57990(17) 0.0275(5) Uani 1 1 d . . . O5 O 0.8184(2) 0.4325(2) 0.55132(13) 0.0449(5) Uani 1 1 d . . . O6 O 0.9129(2) 0.1816(2) 0.52138(14) 0.0491(5) Uani 1 1 d . . . C14 C 0.9253(3) 0.2483(4) 0.4203(2) 0.0484(7) Uani 1 1 d . . . H14A H 1.0100 0.1988 0.4075 0.058 Uiso 1 1 calc R . . H14B H 0.9349 0.3775 0.4238 0.058 Uiso 1 1 calc R . . C15 C 0.8000(6) 0.1990(6) 0.3319(3) 0.0936(16) Uani 1 1 d . . . H15A H 0.7913 0.0710 0.3281 0.140 Uiso 1 1 calc R . . H15B H 0.8095 0.2439 0.2650 0.140 Uiso 1 1 calc R . . H15C H 0.7165 0.2496 0.3442 0.140 Uiso 1 1 calc R . . C5 C 0.6462(3) 0.0617(3) 0.9095(2) 0.0377(6) Uani 1 1 d . . . C16 C 0.8531(2) 0.0274(3) 0.69471(17) 0.0284(5) Uani 1 1 d . . . O7 O 0.92345(18) -0.0778(2) 0.75540(14) 0.0408(4) Uani 1 1 d . . . O8 O 0.73035(16) -0.00614(19) 0.62496(12) 0.0315(4) Uani 1 1 d . . . C17 C 0.6732(3) -0.1803(3) 0.6316(2) 0.0422(6) Uani 1 1 d . . . H17A H 0.6701 -0.2030 0.7046 0.051 Uiso 1 1 calc R . . H17B H 0.7321 -0.2712 0.6129 0.051 Uiso 1 1 calc R . . C18 C 0.5292(3) -0.1844(4) 0.5555(3) 0.0642(9) Uani 1 1 d . . . H18A H 0.4741 -0.0882 0.5715 0.096 Uiso 1 1 calc R . . H18B H 0.4849 -0.2966 0.5619 0.096 Uiso 1 1 calc R . . H18C H 0.5342 -0.1712 0.4830 0.096 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 0.0446(9) 0.0263(8) 0.0435(9) -0.0044(7) 0.0237(8) -0.0076(7) C1 0.0290(10) 0.0270(11) 0.0292(10) -0.0008(8) 0.0117(8) -0.0034(8) C2 0.0401(12) 0.0333(12) 0.0374(11) -0.0083(9) 0.0185(10) -0.0059(10) C3 0.0615(17) 0.0576(17) 0.0341(13) -0.0056(11) 0.0240(12) 0.0012(14) C4 0.089(2) 0.0589(19) 0.0448(15) 0.0072(13) 0.0346(17) -0.0124(16) O2 0.0713(14) 0.0371(10) 0.0806(15) 0.0012(9) 0.0450(13) -0.0134(10) C6 0.0500(15) 0.0312(13) 0.0574(15) -0.0028(11) 0.0314(13) 0.0043(11) C7 0.0601(17) 0.0512(17) 0.0539(16) -0.0247(13) 0.0231(14) -0.0214(14) C8 0.0303(10) 0.0226(10) 0.0317(10) -0.0006(8) 0.0137(9) 0.0016(8) C9 0.0274(10) 0.0261(11) 0.0263(10) 0.0007(8) 0.0122(9) -0.0003(8) C10 0.0310(10) 0.0301(11) 0.0279(10) 0.0022(8) 0.0118(9) -0.0012(8) O3 0.0352(9) 0.0726(13) 0.0596(13) -0.0278(11) 0.0091(9) -0.0055(9) O4 0.0251(9) 0.0902(16) 0.0814(15) -0.0457(13) 0.0183(10) -0.0043(10) C11 0.0254(12) 0.094(2) 0.0583(17) -0.0175(16) 0.0142(13) -0.0052(13) C12 0.0448(15) 0.067(2) 0.072(2) -0.0213(16) 0.0220(16) -0.0088(14) C13 0.0286(10) 0.0251(11) 0.0304(10) -0.0003(8) 0.0110(8) -0.0003(8) O5 0.0637(12) 0.0387(10) 0.0352(9) 0.0097(7) 0.0194(9) 0.0161(8) O6 0.0869(14) 0.0347(9) 0.0404(9) 0.0110(7) 0.0412(10) 0.0170(9) C14 0.0735(19) 0.0451(15) 0.0399(13) 0.0101(11) 0.0370(14) 0.0124(13) C15 0.161(5) 0.081(3) 0.0463(18) -0.0165(18) 0.043(3) -0.054(3) C5 0.0418(13) 0.0280(12) 0.0510(14) 0.0083(10) 0.0255(12) 0.0040(10) C16 0.0307(10) 0.0268(11) 0.0320(10) 0.0015(9) 0.0160(9) 0.0026(9) O7 0.0433(9) 0.0316(9) 0.0446(9) 0.0081(7) 0.0090(8) 0.0071(7) O8 0.0344(8) 0.0234(7) 0.0367(8) 0.0007(6) 0.0108(7) -0.0042(6) C17 0.0477(14) 0.0251(12) 0.0577(16) -0.0063(10) 0.0217(13) -0.0110(10) C18 0.0409(15) 0.0475(17) 0.104(3) -0.0258(16) 0.0208(17) -0.0107(13) _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 C5 1.350(3) . ? O1 C1 1.465(3) . ? C1 C8 1.526(3) . ? C1 C2 1.528(3) . ? C2 C7 1.526(3) . ? C2 C6 1.528(4) . ? C2 C3 1.533(4) . ? C3 C4 1.481(4) . ? C4 C5 1.496(4) . ? O2 C5 1.200(3) . ? C8 C9 1.548(3) . ? C9 C16 1.527(3) . ? C9 C10 1.539(3) . ? C9 C13 1.542(3) . ? C10 O3 1.192(3) . ? C10 O4 1.306(3) . ? O4 C11 1.454(3) . ? C11 C12 1.483(4) . ? C13 O5 1.197(3) . ? C13 O6 1.314(3) . ? O6 C14 1.470(3) . ? C14 C15 1.485(6) . ? C16 O7 1.202(3) . ? C16 O8 1.322(3) . ? O8 C17 1.460(3) . ? C17 C18 1.492(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 O1 C1 121.15(18) . . ? O1 C1 C8 104.30(17) . . ? O1 C1 C2 111.72(16) . . ? C8 C1 C2 114.79(18) . . ? C7 C2 C6 109.7(2) . . ? C7 C2 C1 109.83(18) . . ? C6 C2 C1 111.93(19) . . ? C7 C2 C3 108.4(2) . . ? C6 C2 C3 111.6(2) . . ? C1 C2 C3 105.16(19) . . ? C4 C3 C2 113.9(2) . . ? C3 C4 C5 118.2(2) . . ? C1 C8 C9 115.02(17) . . ? C16 C9 C10 110.10(17) . . ? C16 C9 C13 112.24(17) . . ? C10 C9 C13 106.09(15) . . ? C16 C9 C8 110.21(16) . . ? C10 C9 C8 109.88(16) . . ? C13 C9 C8 108.23(16) . . ? O3 C10 O4 124.1(2) . . ? O3 C10 C9 123.73(19) . . ? O4 C10 C9 112.18(18) . . ? C10 O4 C11 119.1(2) . . ? O4 C11 C12 107.1(2) . . ? O5 C13 O6 124.6(2) . . ? O5 C13 C9 122.83(18) . . ? O6 C13 C9 112.46(17) . . ? C13 O6 C14 117.22(18) . . ? O6 C14 C15 110.2(3) . . ? O2 C5 O1 117.7(2) . . ? O2 C5 C4 122.9(2) . . ? O1 C5 C4 119.2(2) . . ? O7 C16 O8 125.0(2) . . ? O7 C16 C9 124.2(2) . . ? O8 C16 C9 110.72(18) . . ? C16 O8 C17 115.75(18) . . ? O8 C17 C18 107.3(2) . . ? _diffrn_measured_fraction_theta_max 0.914 _diffrn_reflns_theta_full 67.60 _diffrn_measured_fraction_theta_full 0.914 _refine_diff_density_max 0.212 _refine_diff_density_min -0.161 _refine_diff_density_rms 0.035