# Copyright The Royal Society of Chemistry, 1999 # CCDC Number: 182/1195 data_1 # The following CIF file contains the crystallographic data of # of compound (1S,4R,5R)-5e in our paper # D.Enders, J.Vazquez, G.Raabe # Diastereo- and enantioselective synthesis of 2,8-dioxabicyclo[3.3.0] # octan-3-one _audit_creation_date 99-01-25 _audit_creation_method from_xtal_archive_file_using_CIFIO _audit_update_record ? _chemical_compound_source ? _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_analytical ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_sum ? _chemical_formula_weight ? _chemical_melting_point ? _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction xtal_DIFDAT_SORTRF_ADDREF _computing_structure_solution xtal _computing_structure_refinement xtal_CRYLSQ _computing_molecular_graphics xtal _computing_publication_material xtal_BONDLA_CIFIO _cell_length_a 6.250(3) _cell_length_b 9.3530(10) _cell_length_c 19.655(2) _cell_angle_alpha 90.00000 _cell_angle_beta 90.00000 _cell_angle_gamma 90.00000 _cell_volume 1149.0(6) _cell_formula_units_Z ? _cell_measurement_temperature 293 _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _cell_special_details ; ? ; _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M p_21_21_21 _symmetry_space_group_name_Hall p_2ac_2ab loop_ _symmetry_equiv_pos_as_xyz +x,+y,+z 1/2-x,-y,1/2+z 1/2+x,1/2-y,-z -x,1/2+y,1/2-z _exptl_crystal_description irregular _exptl_crystal_preparation ? _exptl_crystal_colour colourless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.3 _exptl_crystal_density_diffrn 1.262 _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_F_000 464 _exptl_absorpt_process_details ? _exptl_absorpt_coefficient_mu 0.690 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_special_details ; ? ; _diffrn_ambient_temperature 298 _diffrn_radiation_wavelength 1.54179\%A _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'xray tube' _diffrn_radiation_monochromator 'graphite' _diffrn_radiation_detector ? _diffrn_measurement_device CAD4 _diffrn_measurement_method \w/2\q _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% ? loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 1 2 2 -1 2 2 1 3 4 loop_ _diffrn_attenuator_code _diffrn_attenuator_scale 1 11.8 _diffrn_reflns_number 6795 _diffrn_reflns_av_R_equivalents .038 _diffrn_reflns_av_sigmaI/netI .036 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 4.5 _diffrn_reflns_theta_max 74.9 _diffrn_reflns_reduction_process perpendicular_monochr_Lp loop_ _atom_type_symbol _atom_type_description _atom_type_oxidation_number _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C ? 0 52 .017 .009 Int._Tables_Vol_IV_Tables_2.2B_and_2.3.1 H ? 0 56 0 0 Int._Tables_Vol_IV_Tables_2.2B_and_2.3.1 O ? 0 12 .047 .032 Int._Tables_Vol_IV_Tables_2.2B_and_2.3.1 loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_calc_attached_atom O1 1.1175(5) .5445(3) .52540(13) .067(2) Uani ? ? O2 1.3897(5) .6537(3) .47517(17) .083(2) Uani ? ? O3 .8878(6) .3505(3) .51533(12) .076(2) Uani ? ? C1 1.2150(7) .6008(5) .4712(2) .059(3) Uani ? ? C2 1.0780(6) .5882(4) .40880(16) .051(3) Uani ? ? C3 .8616(7) .5385(5) .43522(18) .053(3) Uani ? ? C4 .7833(7) .3986(5) .40478(17) .072(3) Uani ? ? C5 .9014(9) .2897(4) .4487(2) .078(3) Uani ? ? C6 .9033(9) .4987(5) .5096(2) .063(3) Uani ? ? C7 1.0701(7) .7288(4) .36801(16) .065(3) Uani ? ? C8 .9279(8) .7181(5) .3063(2) .059(3) Uani ? ? C9 .9844(10) .6317(5) .2524(2) .077(3) Uani ? ? C10 .8529(10) .6187(6) .1958(2) .092(4) Uani ? ? C11 .6589(10) .6919(6) .1942(2) .094(4) Uani ? ? C12 .6034(8) .7801(5) .2474(2) .089(4) Uani ? ? C13 .7357(8) .7908(5) .3030(2) .074(3) Uani ? ? H3 .74620 .61600 .42939 .07800 Uani ? ? H6 .78715 .54760 .54131 .06200 Uani ? ? H2 1.13734 .50878 .37717 .07500 Uani ? ? H9 1.13088 .58038 .25124 .11000 Uani ? ? H10 .88983 .55444 .15762 .13800 Uani ? ? H11 .55923 .67314 .15373 .14100 Uani ? ? H12 .46103 .84230 .24610 .12500 Uani ? ? H13 .68924 .84416 .34415 .10700 Uani ? ? H7A 1.22156 .75784 .35467 .09300 Uani ? ? H7B 1.01504 .80756 .39973 .09300 Uani ? ? H4A .61759 .38682 .41207 .10200 Uani ? ? H4B .81093 .38881 .35620 .10200 Uani ? ? H5A .82285 .19138 .44533 .11100 Uani ? ? H5B 1.04670 .27595 .43063 .11100 Uani ? ? loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 .068(2) .078(2) .0557(14) .006(2) -.012(2) -.0022(17) O2 .043(2) .102(2) .104(2) -.007(2) -.013(3) -.017(2) O3 .096(3) .071(2) .0625(17) -.007(3) .007(3) .0098(15) C1 .045(3) .066(3) .067(3) .007(3) -.008(3) -.007(3) C2 .048(3) .059(3) .047(2) -.006(3) -.000(3) -.008(2) C3 .042(3) .065(3) .050(2) -.005(3) -.004(2) .006(2) C4 .071(3) .075(3) .070(2) -.024(4) -.006(3) -.001(3) C5 .094(4) .058(2) .083(3) -.013(4) -.003(4) .003(3) C6 .060(4) .061(3) .067(3) .007(4) .014(4) .002(3) C7 .075(4) .064(3) .055(2) -.011(3) -.001(3) .002(2) C8 .073(4) .061(3) .042(2) -.014(3) .009(3) .008(2) C9 .097(4) .081(3) .0513(19) .006(4) -.000(3) .003(3) C10 .134(6) .083(4) .058(3) .014(5) -.001(4) -.003(3) C11 .117(5) .103(5) .061(3) -.002(5) -.015(4) .003(3) C12 .094(5) .103(3) .072(2) .012(5) -.008(4) .003(3) C13 .075(4) .097(4) .049(2) .008(4) .000(3) .001(3) H3 .07800 .07800 .07800 .00000 .00000 .00000 H6 .06200 .06200 .06200 .00000 .00000 .00000 H2 .07500 .07500 .07500 .00000 .00000 .00000 H9 .11000 .11000 .11000 .00000 .00000 .00000 H10 .13800 .13800 .13800 .00000 .00000 .00000 H11 .14100 .14100 .14100 .00000 .00000 .00000 H12 .12500 .12500 .12500 .00000 .00000 .00000 H13 .10700 .10700 .10700 .00000 .00000 .00000 H7A .09300 .09300 .09300 .00000 .00000 .00000 H7B .09300 .09300 .09300 .00000 .00000 .00000 H4A .10200 .10200 .10200 .00000 .00000 .00000 H4B .10200 .10200 .10200 .00000 .00000 .00000 H5A .11100 .11100 .11100 .00000 .00000 .00000 H5B .11100 .11100 .11100 .00000 .00000 .00000 _atom_sites_solution_primary ? _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens calculated _refine_special_details sfls:_F____sigma_weight______full_matrix _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme sigma _refine_ls_hydrogen_treatment ? _refine_ls_extinction_method none _refine_ls_extinction_coef .00000 _refine_ls_extinction_expression ? _refine_ls_abs_structure_details none _refine_ls_abs_structure_Flack 0 _refine_ls_number_reflns 808 _refine_ls_number_parameters 145 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_all .088 _refine_ls_R_factor_obs .05 _refine_ls_wR_factor_all .035 _refine_ls_wR_factor_obs .031 _refine_ls_goodness_of_fit_all 1.546 _refine_ls_goodness_of_fit_obs 1.853 _refine_ls_shift/esd_max . _refine_ls_shift/esd_mean . _refine_diff_density_min -.242 _refine_diff_density_max .25 _geom_special_details ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.335(5) . . ? O1 C6 1.440(6) . . ? O2 C1 1.201(6) . . ? O3 C6 1.394(6) . . ? O3 C5 1.430(5) . . ? C1 C2 1.501(6) . . ? C2 H2 1.037(4) . . ? C2 C3 1.521(6) . . ? C2 C7 1.541(5) . . ? C3 H3 1.029(4) . . ? C3 C4 1.520(6) . . ? C3 C6 1.531(6) . . ? C4 H4B .975(3) . . ? C4 H4A 1.052(4) . . ? C4 C5 1.526(6) . . ? C5 H5B .984(5) . . ? C5 H5A 1.044(5) . . ? C6 H6 1.061(5) . . ? C7 H7A 1.019(4) . . ? C7 H7B 1.024(4) . . ? C7 C8 1.508(6) . . ? C8 C9 1.378(6) . . ? C8 C13 1.382(7) . . ? C9 H9 1.033(6) . . ? C9 C10 1.388(7) . . ? C10 H10 .989(5) . . ? C10 C11 1.393(9) . . ? C11 H11 1.025(5) . . ? C11 C12 1.376(7) . . ? C12 H12 1.063(5) . . ? C12 C13 1.375(6) . . ? C13 H13 .993(4) . . ? loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag H5A H5B 1.6329(6) . . ? H4A H4B 1.6329(4) . . ? H7A H7B 1.6330(5) . . ? O3 H6 2.014(3) . . ? C8 H13 2.042(5) . . ? O3 H5B 2.060(3) . . ? C11 H10 2.062(6) . . ? C12 H13 2.065(4) . . ? O3 H5A 2.067(3) . . ? C4 H5B 2.070(4) . . ? C10 H11 2.077(6) . . ? C10 H9 2.082(6) . . ? C9 H10 2.083(4) . . ? C3 H2 2.086(4) . . ? O1 H6 2.088(3) . . ? C8 H7B 2.091(4) . . ? C1 H2 2.096(5) . . ? C2 H7B 2.097(4) . . ? C8 H7A 2.101(5) . . ? C4 H3 2.102(4) . . ? C13 H12 2.105(5) . . ? C8 H9 2.106(4) . . ? C7 H2 2.108(4) . . ? C4 H5A 2.110(4) . . ? C2 H7A 2.111(4) . . ? C12 H11 2.113(4) . . ? C3 H4B 2.115(4) . . ? C5 H4B 2.118(4) . . ? C5 H4A 2.119(5) . . ? C2 H3 2.129(4) . . ? C3 H4A 2.132(4) . . ? C11 H12 2.133(6) . . ? C3 H6 2.138(4) . . ? C6 H3 2.157(5) . . ? O1 O2 2.216(4) . . ? C5 C6 2.292(6) . . ? C1 C6 2.297(7) . . ? H3 H6 2.3052(2) . . ? O3 C4 2.313(4) . . ? H3 H4A 2.3144(3) . . ? O1 O3 2.322(4) . . ? H4A H5A 2.3269(4) . . ? H4B H5B 2.3294(5) . . ? H13 H7B 2.3360(9) . . ? O1 C2 2.341(4) . . ? H10 H11 2.3469(9) . . ? C3 C5 2.356(6) . . ? H2 H4B 2.3645(8) . . ? O3 C3 2.366(5) . . ? C9 C13 2.371(7) . . ? C11 C13 2.380(7) . . ? C4 C6 2.383(6) . . ? O1 C3 2.388(5) . . ? H9 H10 2.3905(5) . . ? C1 C3 2.392(6) . . ? C10 C12 2.395(7) . . ? H12 H13 2.3976(4) . . ? C9 C11 2.401(8) . . ? C8 C12 2.406(7) . . ? C8 C10 2.407(6) . . ? C2 C6 2.412(6) . . ? O2 C2 2.423(5) . . ? O2 H3 2.429(3) . 1_655 ? H2 H7A 2.4288(2) . . ? H6 H7B 2.4638(6) . 3_466 ? H2 H5B 2.4835(2) . . ? H11 H12 2.48514(19) . . ? C4 H2 2.500(4) . . ? C7 C9 2.506(5) . . ? C7 C13 2.517(7) . . ? C1 C7 2.524(6) . . ? H3 H7B 2.5246(6) . . ? C2 C8 2.533(5) . . ? H4B H5A 2.54636(19) . . ? C2 C4 2.557(6) . . ? H2 H9 2.5643(2) . . ? C3 C7 2.571(6) . . ? C7 H3 2.582(4) . . ? C13 H7B 2.586(5) . . ? H3 H4B 2.5977(2) . . ? O2 H7B 2.606(3) . 3_566 ? O1 H5A 2.616(3) . 3_556 ? H11 H4A 2.6245(3) . 4_655 ? H10 H7B 2.6374(2) . 4_745 ? C7 H13 2.655(5) . . ? O3 H5B 2.659(4) . 3_456 ? O3 H4A 2.662(3) . . ? H12 H4B 2.6686(5) . 4_655 ? H9 H7A 2.6848(2) . . ? C1 H7B 2.698(5) . . ? C2 H4B 2.708(4) . . ? C7 H9 2.709(3) . . ? H6 H10 2.7130(3) . 2_665 ? C3 H5B 2.716(4) . . ? C1 H7A 2.722(5) . . ? H12 H7A 2.7235(4) . 1_455 ? H10 H5B 2.7310(2) . 4_755 ? C8 H2 2.736(4) . . ? H3 H13 2.7364(2) . . ? C6 H5B 2.748(5) . . ? O3 H11 2.749(2) . 2_665 ? C10 C13 2.751(7) . . ? C9 C12 2.758(8) . . ? C9 H7A 2.763(5) . . ? H6 H7A 2.7675(2) . 3_466 ? O2 H7A 2.768(3) . . ? C3 H7B 2.782(4) . . ? C8 C11 2.782(7) . . ? O1 H13 2.804(3) . 3_566 ? C6 H4A 2.821(5) . . ? H3 H2 2.8347(10) . . ? O2 H2 2.835(3) . . ? C8 H3 2.839(4) . . ? O3 H5A 2.854(4) . 3_556 ? H10 H7A 2.8703(3) . 4_745 ? C9 H2 2.872(5) . . ? O2 H6 2.885(3) . 3_566 ? C5 H2 2.890(5) . . ? H4A H5B 2.8985(12) . . ? H2 H7B 2.9309(3) . . ? O1 H2 2.935(3) . . ? C10 H5B 2.956(5) . 4_755 ? C2 H5B 2.958(4) . . ? O2 H6 2.974(3) . 1_655 ? C13 H3 2.974(4) . . ? O2 C7 2.987(5) . . ? C6 H2 2.987(5) . . ? H10 H5A 2.9933(5) . 4_755 ? O2 H3 2.994(3) . 3_566 ? H5A H5B 3.0027(5) . 3_456 ? O3 H4A 3.004(3) . 3_556 ? C4 H6 3.024(4) . . ? C13 H9 3.028(5) . 4_755 ? H13 H7A 3.0395(13) . 1_455 ? C1 H3 3.047(5) . . ? C1 H6 3.049(5) . . ? C7 H6 3.064(4) . 3_566 ? O1 H3 3.065(3) . . ? C3 C8 3.069(6) . . ? H11 H4B 3.0756(8) . 4_655 ? H11 H5A 3.0859(9) . 4_655 ? C7 H10 3.097(4) . 4_755 ? C2 C5 3.103(6) . . ? C5 H6 3.105(4) . . ? H9 H13 3.1081(3) . 4_745 ? C2 H9 3.115(3) . . ? H11 H5B 3.1210(9) . 4_755 ? O2 H7B 3.123(3) . . ? O1 C5 3.127(5) . . ? O2 H4A 3.130(3) . 1_655 ? O3 H3 3.131(3) . . ? H6 H4A 3.1364(3) . . ? C2 C9 3.156(5) . . ? O1 H5B 3.158(3) . . ? O1 O2 3.162(4) . 3_466 ? C11 H5B 3.166(5) . 4_755 ? H6 H11 3.1728(3) . 2_665 ? H12 H4A 3.1749(3) . 4_655 ? C6 H5A 3.180(5) . . ? O3 H4B 3.185(2) . . ? C12 H7A 3.192(5) . 1_455 ? C2 H6 3.199(4) . . ? O1 H7B 3.202(3) . 3_566 ? H9 H12 3.2045(7) . 1_655 ? C13 H7A 3.217(5) . . ? C4 H11 3.218(4) . 4_645 ? C5 H3 3.225(4) . . ? O3 C1 3.228(6) . . ? O2 C3 3.237(6) . 1_655 ? C6 H4B 3.237(4) . . ? C9 H4B 3.240(5) . . ? O2 C1 3.243(6) . 3_566 ? C9 H13 3.257(5) . . ? C1 H5A 3.258(5) . 3_556 ? C3 H5A 3.262(4) . . ? C12 H9 3.263(5) . 4_755 ? C6 H11 3.266(4) . 2_665 ? O2 C6 3.266(6) . 3_566 ? C11 H4A 3.267(5) . 4_655 ? C1 H7B 3.269(5) . 3_566 ? O3 C2 3.277(5) . . ? C11 H13 3.279(5) . . ? C12 H10 3.282(5) . . ? H2 H4A 3.2835(13) . 1_655 ? H10 H13 3.2849(10) . 4_745 ? C6 H5A 3.290(5) . 3_556 ? C1 H3 3.297(5) . 3_566 ? C5 H10 3.303(4) . 4_745 ? C5 H5B 3.304(5) . 3_456 ? C8 H10 3.306(4) . . ? C9 H11 3.312(6) . . ? C1 H5B 3.313(5) . . ? C8 H4B 3.314(4) . . ? C13 H9 3.318(5) . . ? C13 H11 3.322(4) . . ? C11 H9 3.324(6) . . ? C1 H6 3.328(5) . 3_566 ? C9 H7B 3.337(4) . . ? C8 H12 3.356(5) . . ? C5 H5A 3.363(5) . 3_556 ? C10 H12 3.369(6) . . ? C4 H12 3.377(4) . 4_645 ? O2 C3 3.379(5) . 3_566 ? C13 H7A 3.384(5) . 1_455 ? O3 C5 3.385(7) . 3_456 ? H9 H4B 3.3860(6) . . ? H9 H12 3.3862(9) . 4_745 ? O1 H3 3.394(3) . 3_566 ? H9 H11 3.4049(10) . 1_655 ? O3 H10 3.409(3) . 2_665 ? C1 H4A 3.419(5) . 1_655 ? C8 H10 3.421(4) . 4_755 ? C1 H3 3.423(5) . 1_655 ? H6 H5B 3.4234(4) . 3_456 ? O1 H11 3.424(3) . 2_665 ? H13 H7A 3.4298(15) . . ? C3 H7A 3.431(4) . . ? H4A H5A 3.4328(5) . 3_456 ? O2 C6 3.435(6) . . ? C2 H4A 3.440(4) . . ? C10 H12 3.440(6) . 4_645 ? O1 C4 3.441(5) . . ? C10 H4B 3.442(6) . 4_755 ? H11 H13 3.4469(4) . 4_645 ? C12 H4B 3.447(5) . 4_655 ? C9 H4B 3.460(5) . 4_755 ? O2 C7 3.461(5) . 3_566 ? O3 H2 3.464(3) . . ? C5 H4A 3.470(4) . 3_556 ? C6 H10 3.474(5) . 2_665 ? H4A H5B 3.4745(3) . 3_456 ? C13 H10 3.486(5) . 4_755 ? C12 H9 3.496(5) . 1_455 ? C10 H5A 3.502(5) . 4_755 ? H2 H4A 3.5106(14) . . ? H10 H12 3.5109(7) . 4_645 ? C6 H7B 3.514(5) . 3_466 ? C11 H2 3.517(6) . 4_755 ? C10 H6 3.522(5) . 2_664 ? H6 H13 3.5226(9) . 3_566 ? O2 C2 3.523(5) . 3_566 ? C2 C13 3.534(6) . . ? C1 C5 3.536(7) . . ? O3 C5 3.539(7) . 3_556 ? C3 H13 3.541(4) . . ? C1 C4 3.544(6) . . ? O1 H7B 3.545(3) . . ? C10 H7A 3.548(6) . 4_745 ? O3 C11 3.550(5) . 2_665 ? O1 C7 3.554(4) . . ? C11 H12 3.554(6) . 4_645 ? O2 C3 3.560(6) . . ? C10 H7B 3.560(5) . 4_745 ? C12 H4A 3.567(4) . 4_655 ? H3 H7A 3.5698(12) . . ? C9 H12 3.573(6) . 1_655 ? C7 H4B 3.577(4) . . ? C7 H12 3.583(4) . 1_655 ? O2 C6 3.587(6) . 1_655 ? C8 H9 3.591(4) . 4_755 ? H9 H4B 3.5936(3) . 4_755 ? C3 C13 3.597(6) . . ? C6 H5B 3.598(5) . 3_456 ? C5 C10 3.604(7) . 4_745 ? C11 H4B 3.605(6) . 4_655 ? O2 H5A 3.610(3) . 3_556 ? O1 C5 3.630(5) . 3_556 ? C12 H2 3.632(5) . 4_755 ? O3 H5A 3.636(4) . 3_456 ? C11 H9 3.638(6) . 1_455 ? C2 H13 3.640(4) . . ? C4 C7 3.643(6) . . ? O2 H13 3.648(3) . 1_655 ? C1 H13 3.669(5) . 3_566 ? C6 C7 3.669(6) . . ? C4 C8 3.673(6) . . ? C6 H7B 3.674(5) . . ? C5 H11 3.678(5) . 4_645 ? C6 H7A 3.687(5) . 3_466 ? C6 H13 3.690(5) . 3_566 ? O2 C4 3.696(5) . 1_655 ? O3 O3 3.696(5) . 3_556 ? O3 O3 3.696(5) . 3_456 ? C8 H12 3.722(5) . 1_655 ? O2 O2 3.737(5) . 3_466 ? O2 O2 3.737(5) . 3_566 ? C13 H10 3.739(4) . . ? C10 H13 3.741(5) . . ? O3 C4 3.743(5) . 3_556 ? C11 H6 3.763(5) . 2_664 ? O2 H13 3.766(3) . 3_566 ? C3 C9 3.777(6) . . ? C2 H6 3.778(4) . 3_566 ? O1 C13 3.781(5) . 3_566 ? C9 H3 3.787(5) . . ? C7 C10 3.789(6) . . ? C7 C12 3.789(6) . . ? C12 H9 3.790(5) . . ? C5 C5 3.792(8) . 3_456 ? C5 C5 3.792(8) . 3_556 ? C9 C13 3.796(7) . 4_745 ? C8 H11 3.804(4) . . ? C9 H12 3.821(6) . . ? C10 H4B 3.825(5) . . ? C9 H5B 3.847(4) . 4_755 ? C2 H4A 3.863(4) . 1_655 ? C1 H6 3.864(5) . 1_655 ? O3 C10 3.864(6) . 2_665 ? C1 C8 3.865(6) . . ? C9 H13 3.871(5) . 4_745 ? C9 H12 3.883(6) . 4_645 ? O1 H7A 3.886(3) . 3_466 ? C7 C10 3.886(7) . 4_755 ? C4 C11 3.894(7) . 4_645 ? C4 C9 3.912(6) . . ? C4 H5B 3.914(4) . 3_456 ? C11 H4B 3.918(6) . 4_755 ? C10 H2 3.921(5) . 4_755 ? C13 H2 3.922(5) . . ? C10 H13 3.924(6) . 4_745 ? C8 H4B 3.926(4) . 4_755 ? C1 H4B 3.927(5) . . ? C13 H4B 3.931(5) . . ? C1 C6 3.945(7) . 3_566 ? C1 C3 3.950(6) . 3_566 ? C12 H7B 3.956(5) . . ? O1 H7A 3.958(3) . . ? C5 H6 3.975(5) . 3_556 ? C11 H13 3.985(6) . 4_645 ? C8 C10 3.990(7) . 4_755 ? C4 C10 3.992(7) . 4_745 ? C12 H3 3.994(4) . . ? C10 C13 4.002(8) . 4_745 ? C4 C12 4.002(6) . 4_645 ? C4 H10 4.005(4) . 4_745 ? C3 H9 4.008(4) . . ? C11 H9 4.010(6) . 4_755 ? C5 C11 4.034(7) . 4_745 ? C6 C11 4.061(7) . 2_665 ? C8 C9 4.073(6) . 4_755 ? C6 C7 4.077(6) . 3_466 ? O1 C7 4.109(5) . 3_566 ? C9 C12 4.112(8) . 1_655 ? C7 C12 4.119(6) . 1_655 ? C4 C5 4.134(6) . 3_456 ? O1 O3 4.140(4) . 3_556 ? C6 C10 4.143(7) . 2_665 ? C1 C3 4.143(7) . 1_655 ? C1 C5 4.144(6) . 3_556 ? O1 C1 4.164(6) . 3_466 ? C9 C12 4.177(7) . 4_745 ? C1 C7 4.177(6) . 3_566 ? C4 C13 4.189(6) . . ? C5 C6 4.200(7) . 3_456 ? O2 C13 4.216(6) . 1_655 ? C5 C6 4.217(7) . 3_556 ? C4 C9 4.229(6) . 4_745 ? C1 C4 4.230(6) . 1_655 ? O1 C3 4.259(5) . 3_566 ? C5 C9 4.279(6) . 4_745 ? O2 O3 4.285(5) . 1_655 ? C7 C11 4.289(7) . . ? O2 O3 4.302(5) . . ? C1 C1 4.340(7) . 3_466 ? C1 C1 4.340(7) . 3_566 ? C11 C12 4.341(7) . 4_645 ? O1 C11 4.345(6) . 2_665 ? O3 C1 4.365(6) . 3_456 ? C1 C2 4.378(6) . 3_566 ? C7 C13 4.390(7) . 1_655 ? C9 C11 4.404(9) . 1_655 ? C10 C12 4.405(8) . 4_645 ? O2 C5 4.409(5) . 3_556 ? C8 C12 4.416(7) . 1_655 ? C2 C10 4.425(6) . . ? C4 C11 4.436(7) . 4_745 ? 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 C6 111.7(3) . . . ? C6 O3 C5 108.5(3) . . . ? O2 C1 O1 121.7(4) . . . ? O2 C1 C2 127.2(4) . . . ? O1 C1 C2 111.1(4) . . . ? H2 C2 C1 110.0(3) . . . ? H2 C2 C3 107.7(3) . . . ? H2 C2 C7 108.1(3) . . . ? C1 C2 C3 104.6(3) . . . ? C1 C2 C7 112.1(3) . . . ? C3 C2 C7 114.2(3) . . . ? H3 C3 C4 109.7(4) . . . ? H3 C3 C2 111.7(4) . . . ? H3 C3 C6 113.4(4) . . . ? C4 C3 C2 114.5(3) . . . ? C4 C3 C6 102.8(3) . . . ? C2 C3 C6 104.4(3) . . . ? H4B C4 H4A 107.3(4) . . . ? H4B C4 C3 114.2(4) . . . ? H4B C4 C5 113.9(4) . . . ? H4A C4 C3 110.7(4) . . . ? H4A C4 C5 109.2(4) . . . ? C3 C4 C5 101.3(3) . . . ? H5B C5 H5A 107.2(4) . . . ? H5B C5 O3 116.0(5) . . . ? H5B C5 C4 109.2(4) . . . ? H5A C5 O3 112.3(4) . . . ? H5A C5 C4 108.9(4) . . . ? O3 C5 C4 102.9(3) . . . ? H6 C6 O3 109.5(4) . . . ? H6 C6 O1 112.4(4) . . . ? H6 C6 C3 109.9(4) . . . ? O3 C6 O1 110.1(4) . . . ? O3 C6 C3 107.9(3) . . . ? O1 C6 C3 107.0(4) . . . ? H7A C7 H7B 106.1(4) . . . ? H7A C7 C8 111.0(3) . . . ? H7A C7 C2 109.4(4) . . . ? H7B C7 C8 109.9(4) . . . ? H7B C7 C2 107.9(3) . . . ? C8 C7 C2 112.4(3) . . . ? C9 C8 C13 118.4(4) . . . ? C9 C8 C7 120.4(4) . . . ? C13 C8 C7 121.1(4) . . . ? H9 C9 C8 121.0(5) . . . ? H9 C9 C10 117.8(4) . . . ? C8 C9 C10 121.0(5) . . . ? H10 C10 C9 121.5(6) . . . ? H10 C10 C11 119.0(5) . . . ? C9 C10 C11 119.4(5) . . . ? H11 C11 C12 122.6(5) . . . ? H11 C11 C10 117.6(5) . . . ? C12 C11 C10 119.8(5) . . . ? H12 C12 C13 118.8(4) . . . ? H12 C12 C11 121.4(4) . . . ? C13 C12 C11 119.8(5) . . . ? H13 C13 C12 120.5(5) . . . ? H13 C13 C8 117.6(4) . . . ? C12 C13 C8 121.6(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 C6 O1 C1 O2 175.1(4) . . . . ? C6 O1 C1 C2 -4.7(5) . . . . ? C1 O1 C6 O3 114.5(4) . . . . ? C1 O1 C6 C3 -2.5(5) . . . . ? C1 O1 C6 H6 -123.2(4) . . . . ? C6 O3 C5 C4 -36.1(5) . . . . ? C6 O3 C5 H5A -153.1(4) . . . . ? C6 O3 C5 H5B 83.1(5) . . . . ? C5 O3 C6 O1 -99.8(4) . . . . ? C5 O3 C6 C3 16.6(5) . . . . ? C5 O3 C6 H6 136.1(4) . . . . ? O1 C1 C2 C3 9.8(5) . . . . ? O1 C1 C2 C7 134.1(4) . . . . ? O1 C1 C2 H2 -105.6(4) . . . . ? O2 C1 C2 C3 -169.9(5) . . . . ? O2 C1 C2 C7 -45.6(6) . . . . ? O2 C1 C2 H2 74.7(6) . . . . ? C1 C2 C3 C4 -122.1(4) . . . . ? C1 C2 C3 C6 -10.6(4) . . . . ? C1 C2 C3 H3 112.4(4) . . . . ? C7 C2 C3 C4 114.9(4) . . . . ? C7 C2 C3 C6 -133.5(3) . . . . ? C7 C2 C3 H3 -10.5(4) . . . . ? H2 C2 C3 C4 -5.1(4) . . . . ? H2 C2 C3 C6 106.5(4) . . . . ? H2 C2 C3 H3 -130.6(3) . . . . ? C1 C2 C7 C8 -178.5(4) . . . . ? C1 C2 C7 H7A 57.8(4) . . . . ? C1 C2 C7 H7B -57.2(5) . . . . ? C3 C2 C7 C8 -59.7(4) . . . . ? C3 C2 C7 H7A 176.6(3) . . . . ? C3 C2 C7 H7B 61.6(4) . . . . ? H2 C2 C7 C8 60.1(5) . . . . ? H2 C2 C7 H7A -63.6(4) . . . . ? H2 C2 C7 H7B -178.6(3) . . . . ? C2 C3 C4 C5 82.6(4) . . . . ? C2 C3 C4 H4A -161.6(3) . . . . ? C2 C3 C4 H4B -40.3(5) . . . . ? C6 C3 C4 C5 -29.9(4) . . . . ? C6 C3 C4 H4A 85.8(4) . . . . ? C6 C3 C4 H4B -152.9(4) . . . . ? H3 C3 C4 C5 -150.8(3) . . . . ? H3 C3 C4 H4A -35.1(4) . . . . ? H3 C3 C4 H4B 86.2(5) . . . . ? C2 C3 C6 O1 8.3(4) . . . . ? C2 C3 C6 O3 -110.1(4) . . . . ? C2 C3 C6 H6 130.6(4) . . . . ? C4 C3 C6 O1 128.1(4) . . . . ? C4 C3 C6 O3 9.7(5) . . . . ? C4 C3 C6 H6 -109.6(4) . . . . ? H3 C3 C6 O1 -113.5(4) . . . . ? H3 C3 C6 O3 128.1(4) . . . . ? H3 C3 C6 H6 8.7(6) . . . . ? C3 C4 C5 O3 40.4(4) . . . . ? C3 C4 C5 H5A 159.8(4) . . . . ? C3 C4 C5 H5B -83.3(4) . . . . ? H4A C4 C5 O3 -76.5(4) . . . . ? H4A C4 C5 H5A 42.9(5) . . . . ? H4A C4 C5 H5B 159.8(4) . . . . ? H4B C4 C5 O3 163.5(4) . . . . ? H4B C4 C5 H5A -77.0(5) . . . . ? H4B C4 C5 H5B 39.8(6) . . . . ? C2 C7 C8 C9 -67.8(5) . . . . ? C2 C7 C8 C13 110.4(5) . . . . ? H7A C7 C8 C9 55.0(5) . . . . ? H7A C7 C8 C13 -126.8(5) . . . . ? H7B C7 C8 C9 172.1(4) . . . . ? H7B C7 C8 C13 -9.8(6) . . . . ? C7 C8 C9 C10 178.7(4) . . . . ? C7 C8 C9 H9 -5.8(7) . . . . ? C13 C8 C9 C10 .6(7) . . . . ? C13 C8 C9 H9 176.1(4) . . . . ? C7 C8 C13 C12 -179.1(4) . . . . ? C7 C8 C13 H13 -4.7(7) . . . . ? C9 C8 C13 C12 -.9(7) . . . . ? C9 C8 C13 H13 173.4(4) . . . . ? C8 C9 C10 C11 -1.3(8) . . . . ? C8 C9 C10 H10 -177.9(5) . . . . ? H9 C9 C10 C11 -176.9(5) . . . . ? H9 C9 C10 H10 6.4(8) . . . . ? C9 C10 C11 C12 2.3(8) . . . . ? C9 C10 C11 H11 -174.6(5) . . . . ? H10 C10 C11 C12 179.1(5) . . . . ? H10 C10 C11 H11 2.1(9) . . . . ? C10 C11 C12 C13 -2.7(8) . . . . ? C10 C11 C12 H12 176.1(5) . . . . ? H11 C11 C12 C13 174.1(5) . . . . ? H11 C11 C12 H12 -7.1(8) . . . . ? C11 C12 C13 C8 2.0(7) . . . . ? C11 C12 C13 H13 -172.2(5) . . . . ? H12 C12 C13 C8 -176.9(4) . . . . ? H12 C12 C13 H13 9.0(8) . . . . ? _reflns_limit_h_min 0 _reflns_limit_h_max 7 _reflns_limit_k_min 0 _reflns_limit_k_max 11 _reflns_limit_l_min 0 _reflns_limit_l_max 24 _reflns_number_total 1392 _reflns_number_observed 815 _reflns_observed_criterion refl_observed_if_F_____.000_sigma(F___) _reflns_d_resolution_high .798 _reflns_d_resolution_low 9.828 loop_ _reflns_scale_group_code _reflns_scale_meas_F ? 1.0667 loop_ _refln_index_h _refln_index_k _refln_index_l _refln_F_squared_meas _refln_F_squared_calc _refln_F_squared_sigma _refln_observed_status _refln_scale_group_code ? ? ? ? ? ? ? ? _publ_requested_journal 'J. Chem. Soc., Chem. Commun.' _publ_requested_coeditor_name ? _publ_contact_author ; Prof. Dr. Dieter Enders RWTH-Aachen Institut fuer Organische Chemie? institute Prof.-Pirlet-Strasse 1 D-52056 Aachen Germany ; _publ_contact_letter ; ? letter to co-editor ; _publ_contact_author_phone '++49 (0)241 80 4676' _publ_contact_author_fax '++49 (0)241 8888 127' _publ_contact_author_email Enders@RWTH-Aachen.de loop_ _publ_author_name _publ_author_address 'Enders, Dieter' ; RWTH-Aachen Institut fuer Organische Chemie? institute Prof.-Pirlet-Strasse 1 D-52056 Aachen Germany ; 'Vazquez, Juan' ; RWTH-Aachen Institut fuer Organische Chemie? institute Prof.-Pirlet-Strasse 1 D-52056 Aachen Germany ; 'Raabe, Gerhard' ; RWTH-Aachen Institut fuer Organische Chemie? institute Prof.-Pirlet-Strasse 1 D-52056 Aachen Germany ; _publ_section_title ; ? ; _publ_section_abstract ; ? ; _publ_section_comment ; ? ; _publ_section_experimental ; ? ; _publ_section_references ; ? ; _publ_section_figure_captions ; ? ; _publ_section_acknowledgements ; ? ;