# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Keisuke Suzuki' _publ_contact_author_email ksuzuki@chem.titech.ac.jp _publ_section_title ; Siloxy(trialkoxy)ethene Undergoes Regioselective [2+2] Cycloaddition to Ynones and Ynoates en route to Functionalized Cyclobutenediones ; loop_ _publ_author_name 'Keisuke Suzuki' 'Toshiyuki Hamura' # Attachment 'CCDC-662792--ia-.CIF.txt' data_shelxl _database_code_depnum_ccdc_archive 'CCDC 662792' #TrackingRef 'CCDC-662792--ia-.CIF.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H30 O5 Si' _chemical_formula_weight 318.48 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' Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.501(5) _cell_length_b 10.005(4) _cell_length_c 10.189(4) _cell_angle_alpha 68.89(4) _cell_angle_beta 84.74(4) _cell_angle_gamma 85.22(4) _cell_volume 898.4(7) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.177 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 348 _exptl_absorpt_coefficient_mu 0.148 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9298 _exptl_absorpt_correction_T_max 0.9782 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8631 _diffrn_reflns_av_R_equivalents 0.0242 _diffrn_reflns_av_sigmaI/netI 0.0289 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 4.07 _diffrn_reflns_theta_max 27.47 _reflns_number_total 4054 _reflns_number_gt 3285 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1216P)^2^+0.8595P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4054 _refine_ls_number_parameters 195 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0754 _refine_ls_R_factor_gt 0.0611 _refine_ls_wR_factor_ref 0.2075 _refine_ls_wR_factor_gt 0.1869 _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_restrained_S_all 1.087 _refine_ls_shift/su_max 0.007 _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 Si1 Si 0.83198(7) 0.29065(7) 0.72928(7) 0.0209(2) Uani 1 1 d . . . O1 O 0.52262(19) 0.2406(2) 0.5794(2) 0.0308(4) Uani 1 1 d . . . O2 O 0.7175(2) 0.1829(2) 0.71164(19) 0.0265(4) Uani 1 1 d . . . O3 O 0.87481(18) 0.2326(2) 0.45822(18) 0.0252(4) Uani 1 1 d . . . O4 O 0.6741(2) 0.2728(2) 0.3327(2) 0.0293(4) Uani 1 1 d . . . O5 O 0.6403(2) -0.2457(2) 0.6756(3) 0.0371(5) Uani 1 1 d . . . C1 C 0.6542(3) 0.1630(3) 0.6037(3) 0.0233(5) Uani 1 1 d . . . C2 C 0.7397(3) 0.1889(3) 0.4559(3) 0.0234(5) Uani 1 1 d . . . C3 C 0.7255(3) 0.0317(3) 0.4876(3) 0.0271(5) Uani 1 1 d . . . H1 H 0.7551 -0.0291 0.4358 0.033 Uiso 1 1 calc R . . C4 C 0.6568(3) 0.0069(3) 0.6138(3) 0.0251(5) Uani 1 1 d . . . C5 C 0.6096(3) -0.1298(3) 0.7252(3) 0.0305(6) Uani 1 1 d . . . H2 H 0.5053 -0.1205 0.7472 0.037 Uiso 1 1 calc R . . C6 C 0.6858(4) -0.1637(3) 0.8586(3) 0.0394(7) Uani 1 1 d . . . H3 H 0.6241 -0.2162 0.9403 0.047 Uiso 1 1 calc R . . H4 H 0.7100 -0.0742 0.8674 0.047 Uiso 1 1 calc R . . H5 H 0.7725 -0.2227 0.8543 0.047 Uiso 1 1 calc R . . C7 C 0.4204(3) 0.1981(3) 0.6970(3) 0.0349(6) Uani 1 1 d . . . H6 H 0.3659 0.1216 0.6913 0.042 Uiso 1 1 calc R . . H7 H 0.3564 0.2806 0.6953 0.042 Uiso 1 1 calc R . . H8 H 0.4690 0.1629 0.7848 0.042 Uiso 1 1 calc R . . C8 C 0.9752(3) 0.2051(3) 0.3566(3) 0.0321(6) Uani 1 1 d . . . H9 H 1.0217 0.1097 0.3984 0.039 Uiso 1 1 calc R . . H10 H 1.0463 0.2776 0.3272 0.039 Uiso 1 1 calc R . . H11 H 0.9265 0.2093 0.2744 0.039 Uiso 1 1 calc R . . C9 C 0.6714(3) 0.4243(3) 0.3008(3) 0.0360(6) Uani 1 1 d . . . H12 H 0.5850 0.4548 0.3450 0.043 Uiso 1 1 calc R . . H13 H 0.6730 0.4739 0.1984 0.043 Uiso 1 1 calc R . . H14 H 0.7543 0.4479 0.3370 0.043 Uiso 1 1 calc R . . C10 C 0.8130(4) 0.4747(3) 0.5968(3) 0.0350(6) Uani 1 1 d . . . H15 H 0.8745 0.4813 0.5123 0.042 Uiso 1 1 calc R . . H16 H 0.8402 0.5439 0.6365 0.042 Uiso 1 1 calc R . . H17 H 0.7144 0.4960 0.5718 0.042 Uiso 1 1 calc R . . C11 C 1.0157(3) 0.2108(4) 0.7244(3) 0.0382(7) Uani 1 1 d . . . H18 H 1.0396 0.1512 0.8203 0.046 Uiso 1 1 calc R . . H19 H 1.0819 0.2877 0.6850 0.046 Uiso 1 1 calc R . . H20 H 1.0222 0.1516 0.6654 0.046 Uiso 1 1 calc R . . C12 C 0.7854(3) 0.2970(3) 0.9113(3) 0.0272(5) Uani 1 1 d . . . C13 C 0.6363(4) 0.3662(4) 0.9199(4) 0.0458(8) Uani 1 1 d . . . H21 H 0.6420 0.4700 0.8938 0.055 Uiso 1 1 calc R . . H22 H 0.5939 0.3256 1.0164 0.055 Uiso 1 1 calc R . . H23 H 0.5776 0.3471 0.8550 0.055 Uiso 1 1 calc R . . C14 C 0.8891(4) 0.3902(4) 0.9427(4) 0.0464(8) Uani 1 1 d . . . H24 H 0.9707 0.3298 0.9873 0.056 Uiso 1 1 calc R . . H25 H 0.8413 0.4358 1.0063 0.056 Uiso 1 1 calc R . . H26 H 0.9215 0.4642 0.8543 0.056 Uiso 1 1 calc R . . C15 C 0.7930(5) 0.1466(4) 1.0228(3) 0.0557(10) Uani 1 1 d . . . H27 H 0.7005 0.1050 1.0374 0.067 Uiso 1 1 calc R . . H28 H 0.8189 0.1519 1.1116 0.067 Uiso 1 1 calc R . . H29 H 0.8643 0.0863 0.9912 0.067 Uiso 1 1 calc R . . H30 H 0.574(5) -0.237(5) 0.619(5) 0.061(13) Uiso 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 Si1 0.0192(3) 0.0221(4) 0.0213(3) -0.0072(3) -0.0015(2) -0.0022(2) O1 0.0201(9) 0.0292(10) 0.0406(11) -0.0111(8) 0.0010(8) 0.0033(7) O2 0.0285(9) 0.0291(9) 0.0239(9) -0.0114(7) 0.0027(7) -0.0088(7) O3 0.0184(8) 0.0350(10) 0.0258(9) -0.0149(8) 0.0005(7) -0.0045(7) O4 0.0304(10) 0.0316(10) 0.0273(9) -0.0107(8) -0.0087(8) -0.0008(8) O5 0.0334(11) 0.0261(10) 0.0559(13) -0.0181(10) -0.0125(10) 0.0020(8) C1 0.0176(11) 0.0259(12) 0.0275(12) -0.0109(10) -0.0001(9) -0.0017(9) C2 0.0194(11) 0.0293(12) 0.0240(11) -0.0119(10) -0.0030(9) -0.0017(9) C3 0.0243(12) 0.0286(13) 0.0338(13) -0.0169(11) -0.0053(10) -0.0012(10) C4 0.0174(11) 0.0273(12) 0.0340(13) -0.0140(11) -0.0051(9) -0.0012(9) C5 0.0239(12) 0.0235(12) 0.0441(16) -0.0123(12) 0.0010(11) -0.0028(10) C6 0.0479(18) 0.0322(15) 0.0340(15) -0.0069(12) 0.0027(13) -0.0089(13) C7 0.0223(13) 0.0423(16) 0.0439(16) -0.0217(14) 0.0071(11) -0.0032(11) C8 0.0254(13) 0.0426(16) 0.0292(13) -0.0149(12) 0.0046(10) -0.0033(11) C9 0.0398(16) 0.0311(14) 0.0320(14) -0.0042(11) -0.0102(12) 0.0023(12) C10 0.0527(18) 0.0248(13) 0.0266(13) -0.0077(11) -0.0026(12) -0.0042(12) C11 0.0243(13) 0.0529(19) 0.0359(15) -0.0147(14) -0.0046(11) 0.0049(12) C12 0.0306(13) 0.0280(13) 0.0246(12) -0.0103(10) -0.0027(10) -0.0046(10) C13 0.0369(16) 0.068(2) 0.0429(17) -0.0344(17) 0.0024(13) 0.0009(15) C14 0.051(2) 0.062(2) 0.0389(17) -0.0296(16) -0.0049(14) -0.0171(17) C15 0.099(3) 0.0391(18) 0.0231(15) -0.0044(13) -0.0015(16) -0.0064(19) _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 Si1 O2 1.658(2) . ? Si1 C10 1.856(3) . ? Si1 C11 1.862(3) . ? Si1 C12 1.890(3) . ? O1 C1 1.409(3) . ? O1 C7 1.430(3) . ? O2 C1 1.382(3) . ? O3 C2 1.395(3) . ? O3 C8 1.428(3) . ? O4 C2 1.403(3) . ? O4 C9 1.429(4) . ? O5 C5 1.423(3) . ? C1 C4 1.526(4) . ? C1 C2 1.588(4) . ? C2 C3 1.503(4) . ? C3 C4 1.335(4) . ? C4 C5 1.500(4) . ? C5 C6 1.514(4) . ? C12 C15 1.525(4) . ? C12 C13 1.533(4) . ? C12 C14 1.539(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 O2 Si1 C10 112.06(13) . . ? O2 Si1 C11 110.20(14) . . ? C10 Si1 C11 112.06(16) . . ? O2 Si1 C12 104.56(11) . . ? C10 Si1 C12 109.18(13) . . ? C11 Si1 C12 108.43(14) . . ? C1 O1 C7 114.2(2) . . ? C1 O2 Si1 137.82(17) . . ? C2 O3 C8 113.7(2) . . ? C2 O4 C9 115.2(2) . . ? O2 C1 O1 111.1(2) . . ? O2 C1 C4 114.2(2) . . ? O1 C1 C4 116.2(2) . . ? O2 C1 C2 120.0(2) . . ? O1 C1 C2 108.4(2) . . ? C4 C1 C2 84.88(19) . . ? O3 C2 O4 112.1(2) . . ? O3 C2 C3 117.0(2) . . ? O4 C2 C3 111.2(2) . . ? O3 C2 C1 110.25(19) . . ? O4 C2 C1 118.6(2) . . ? C3 C2 C1 85.50(19) . . ? C4 C3 C2 95.4(2) . . ? C3 C4 C5 131.2(2) . . ? C3 C4 C1 94.2(2) . . ? C5 C4 C1 134.5(2) . . ? O5 C5 C4 109.6(2) . . ? O5 C5 C6 107.9(2) . . ? C4 C5 C6 111.3(2) . . ? C15 C12 C13 109.3(3) . . ? C15 C12 C14 109.2(3) . . ? C13 C12 C14 107.3(3) . . ? C15 C12 Si1 110.8(2) . . ? C13 C12 Si1 110.6(2) . . ? C14 C12 Si1 109.5(2) . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.504 _refine_diff_density_min -0.533 _refine_diff_density_rms 0.087 # Attachment 'CCDC-709482--12-.cif.txt' data_iwata _database_code_depnum_ccdc_archive 'CCDC 709482' #TrackingRef 'CCDC-709482--12-.cif.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H16 O5' _chemical_formula_sum 'C19 H16 O5' _chemical_formula_weight 324.32 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 'P 21/c' _symmetry_int_tables_number 14 _symmetry_space_group_name_Hall '-P 2ybc' 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 9.8511(9) _cell_length_b 9.3112(9) _cell_length_c 18.1359(17) _cell_angle_alpha 90.00 _cell_angle_beta 100.071(2) _cell_angle_gamma 90.00 _cell_volume 1637.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 11394 _cell_measurement_theta_min 2.10 _cell_measurement_theta_max 27.50 _exptl_crystal_description platelet _exptl_crystal_colour yellow _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.315 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type none _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'rotating anode x-ray tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD area detector system' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11394 _diffrn_reflns_av_R_equivalents 0.0227 _diffrn_reflns_av_sigmaI/netI 0.0212 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3762 _reflns_number_gt 3318 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT & SADABS' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP-3 _computing_publication_material SHELXL-97 _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^)+(0.0463P)^2^+0.4326P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3762 _refine_ls_number_parameters 281 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0405 _refine_ls_R_factor_gt 0.0359 _refine_ls_wR_factor_ref 0.0968 _refine_ls_wR_factor_gt 0.0929 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _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 H17 H -0.3431(14) 1.0003(16) 0.0057(7) 0.035(3) Uiso 1 1 d . . . H7 H 0.3971(15) 0.7356(17) 0.2623(9) 0.045(4) Uiso 1 1 d . . . H10 H 0.5854(15) 0.6148(16) 0.0508(8) 0.043(4) Uiso 1 1 d . . . H11 H 0.3822(15) 0.7511(16) 0.0389(9) 0.043(4) Uiso 1 1 d . . . H13 H -0.0739(15) 0.6667(16) 0.0081(8) 0.041(4) Uiso 1 1 d . . . H8 H 0.6033(17) 0.5974(18) 0.2775(10) 0.056(4) Uiso 1 1 d . . . H14 H -0.2310(16) 0.5547(18) -0.0889(9) 0.050(4) Uiso 1 1 d . . . H15 H -0.4442(16) 0.6576(16) -0.1339(9) 0.045(4) Uiso 1 1 d . . . H9 H 0.6977(16) 0.5384(16) 0.1708(8) 0.042(4) Uiso 1 1 d . . . H16 H -0.4995(17) 0.8895(17) -0.0891(8) 0.048(4) Uiso 1 1 d . . . H19A H -0.307(2) 0.957(2) 0.2352(10) 0.071(5) Uiso 1 1 d . . . H19B H -0.2063(19) 0.859(2) 0.1965(11) 0.068(5) Uiso 1 1 d . . . H18C H -0.150(2) 1.387(2) 0.0634(12) 0.075(6) Uiso 1 1 d . . . H19C H -0.142(2) 0.979(3) 0.2530(13) 0.094(7) Uiso 1 1 d . . . H18B H -0.204(2) 1.322(2) 0.1349(12) 0.081(6) Uiso 1 1 d . . . H18A H -0.048(2) 1.325(2) 0.1338(13) 0.091(7) Uiso 1 1 d . . . C1 C 0.02954(10) 0.90324(12) 0.11337(6) 0.0301(2) Uani 1 1 d . . . C2 C -0.10129(10) 0.91962(11) 0.07401(6) 0.0266(2) Uani 1 1 d . . . C3 C -0.12779(10) 1.05965(11) 0.11422(6) 0.0294(2) Uani 1 1 d . . . C4 C 0.02296(11) 1.03598(12) 0.15764(7) 0.0352(3) Uani 1 1 d . . . C5 C 0.13656(10) 0.79173(12) 0.11583(6) 0.0309(2) Uani 1 1 d . . . C6 C 0.37593(10) 0.75515(11) 0.15032(6) 0.0288(2) Uani 1 1 d . . . C7 C 0.43743(12) 0.71083(13) 0.22053(7) 0.0345(2) Uani 1 1 d . . . C8 C 0.55803(12) 0.62991(14) 0.22775(7) 0.0376(3) Uani 1 1 d . . . C9 C 0.61305(11) 0.59553(13) 0.16523(7) 0.0339(2) Uani 1 1 d . . . C10 C 0.54773(12) 0.63858(13) 0.09483(7) 0.0353(2) Uani 1 1 d . . . C11 C 0.42766(12) 0.71972(13) 0.08687(7) 0.0343(2) Uani 1 1 d . . . C12 C -0.19359(10) 0.84536(11) 0.01582(6) 0.0253(2) Uani 1 1 d . . . C13 C -0.16109(11) 0.71198(12) -0.01251(6) 0.0311(2) Uani 1 1 d . . . C14 C -0.25370(12) 0.64522(13) -0.06802(7) 0.0353(2) Uani 1 1 d . . . C15 C -0.37899(12) 0.70952(13) -0.09608(6) 0.0346(2) Uani 1 1 d . . . C16 C -0.41259(11) 0.84159(13) -0.06898(6) 0.0331(2) Uani 1 1 d . . . C17 C -0.32082(11) 0.90915(12) -0.01321(6) 0.0287(2) Uani 1 1 d . . . C18 C -0.13866(19) 1.31267(15) 0.10189(11) 0.0533(4) Uani 1 1 d . . . C19 C -0.22251(19) 0.95346(17) 0.21388(10) 0.0522(4) Uani 1 1 d . . . O1 O 0.26075(7) 0.84746(9) 0.14481(5) 0.0356(2) Uani 1 1 d . . . O2 O 0.11792(8) 0.66902(9) 0.09749(6) 0.0480(3) Uani 1 1 d . . . O3 O -0.14756(8) 1.17521(8) 0.06541(5) 0.0360(2) Uani 1 1 d . . . O4 O -0.23511(8) 1.05861(9) 0.15561(5) 0.0361(2) Uani 1 1 d . . . O5 O 0.09759(10) 1.09941(11) 0.20622(6) 0.0564(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0222(5) 0.0269(5) 0.0397(6) -0.0035(4) 0.0013(4) 0.0030(4) C2 0.0221(4) 0.0230(5) 0.0345(5) -0.0017(4) 0.0042(4) 0.0026(4) C3 0.0225(5) 0.0265(5) 0.0379(6) -0.0059(4) 0.0014(4) 0.0039(4) C4 0.0251(5) 0.0322(6) 0.0454(6) -0.0078(5) -0.0020(4) 0.0031(4) C5 0.0215(5) 0.0290(5) 0.0402(6) -0.0012(4) 0.0000(4) 0.0040(4) C6 0.0181(4) 0.0258(5) 0.0412(6) -0.0007(4) 0.0010(4) 0.0023(4) C7 0.0290(5) 0.0407(6) 0.0332(6) -0.0052(5) 0.0039(4) 0.0052(4) C8 0.0324(6) 0.0423(6) 0.0345(6) -0.0007(5) -0.0043(5) 0.0093(5) C9 0.0230(5) 0.0323(5) 0.0451(6) -0.0032(5) 0.0021(4) 0.0054(4) C10 0.0306(5) 0.0389(6) 0.0382(6) 0.0002(5) 0.0112(5) 0.0028(5) C11 0.0303(5) 0.0375(6) 0.0343(6) 0.0063(5) 0.0033(4) 0.0037(4) C12 0.0218(4) 0.0244(5) 0.0295(5) -0.0005(4) 0.0039(4) 0.0008(4) C13 0.0268(5) 0.0280(5) 0.0377(6) -0.0041(4) 0.0038(4) 0.0041(4) C14 0.0389(6) 0.0292(5) 0.0368(6) -0.0072(5) 0.0042(5) 0.0013(5) C15 0.0369(6) 0.0353(6) 0.0289(5) -0.0013(4) -0.0017(4) -0.0045(5) C16 0.0282(5) 0.0367(6) 0.0321(5) 0.0033(4) -0.0013(4) 0.0029(4) C17 0.0262(5) 0.0271(5) 0.0319(5) -0.0002(4) 0.0027(4) 0.0048(4) C18 0.0653(10) 0.0248(6) 0.0723(10) -0.0093(6) 0.0194(8) 0.0044(6) C19 0.0586(9) 0.0458(8) 0.0572(9) 0.0038(7) 0.0242(8) 0.0057(7) O1 0.0204(4) 0.0302(4) 0.0534(5) -0.0059(3) -0.0018(3) 0.0053(3) O2 0.0268(4) 0.0289(4) 0.0830(7) -0.0097(4) -0.0053(4) 0.0063(3) O3 0.0362(4) 0.0229(4) 0.0483(5) -0.0025(3) 0.0052(4) 0.0047(3) O4 0.0296(4) 0.0369(4) 0.0429(4) -0.0057(3) 0.0091(3) 0.0059(3) O5 0.0376(5) 0.0524(6) 0.0701(7) -0.0286(5) -0.0157(5) 0.0053(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.3683(14) . ? C1 C5 1.4748(14) . ? C1 C4 1.4814(15) . ? C2 C12 1.4432(14) . ? C2 C3 1.5383(14) . ? C3 O3 1.3853(14) . ? C3 O4 1.3995(13) . ? C3 C4 1.5700(15) . ? C4 O5 1.1996(14) . ? C5 O2 1.1952(14) . ? C5 O1 1.3481(13) . ? C6 C7 1.3744(16) . ? C6 C11 1.3776(16) . ? C6 O1 1.4130(12) . ? C7 C8 1.3935(16) . ? C7 H7 0.943(15) . ? C8 C9 1.3773(17) . ? C8 H8 0.981(17) . ? C9 C10 1.3846(17) . ? C9 H9 0.979(15) . ? C10 C11 1.3896(16) . ? C10 H10 0.963(15) . ? C11 H11 0.952(15) . ? C12 C13 1.4022(14) . ? C12 C17 1.4036(14) . ? C13 C14 1.3824(16) . ? C13 H13 0.971(15) . ? C14 C15 1.3861(17) . ? C14 H14 0.966(16) . ? C15 C16 1.3856(17) . ? C15 H15 0.982(16) . ? C16 C17 1.3844(16) . ? C16 H16 0.978(16) . ? C17 H17 0.955(14) . ? C18 O3 1.4364(15) . ? C18 H18C 0.98(2) . ? C18 H18B 0.96(2) . ? C18 H18A 0.98(2) . ? C19 O4 1.4300(18) . ? C19 H19A 0.97(2) . ? C19 H19B 0.95(2) . ? C19 H19C 0.99(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 C2 C1 C5 134.22(10) . . ? C2 C1 C4 93.63(9) . . ? C5 C1 C4 132.05(10) . . ? C1 C2 C12 138.04(10) . . ? C1 C2 C3 93.99(8) . . ? C12 C2 C3 127.97(9) . . ? O3 C3 O4 108.25(8) . . ? O3 C3 C2 111.83(9) . . ? O4 C3 C2 117.08(9) . . ? O3 C3 C4 116.39(9) . . ? O4 C3 C4 117.84(9) . . ? C2 C3 C4 83.96(7) . . ? O5 C4 C1 136.85(11) . . ? O5 C4 C3 134.73(11) . . ? C1 C4 C3 88.42(8) . . ? O2 C5 O1 124.14(10) . . ? O2 C5 C1 126.19(10) . . ? O1 C5 C1 109.63(9) . . ? C7 C6 C11 122.31(10) . . ? C7 C6 O1 117.81(10) . . ? C11 C6 O1 119.76(10) . . ? C6 C7 C8 118.68(11) . . ? C6 C7 H7 119.4(9) . . ? C8 C7 H7 121.9(9) . . ? C9 C8 C7 120.00(11) . . ? C9 C8 H8 120.2(10) . . ? C7 C8 H8 119.8(10) . . ? C8 C9 C10 120.37(10) . . ? C8 C9 H9 119.5(8) . . ? C10 C9 H9 120.1(8) . . ? C9 C10 C11 120.20(11) . . ? C9 C10 H10 120.9(9) . . ? C11 C10 H10 118.9(9) . . ? C6 C11 C10 118.41(11) . . ? C6 C11 H11 120.4(9) . . ? C10 C11 H11 121.2(9) . . ? C13 C12 C17 118.91(10) . . ? C13 C12 C2 122.50(9) . . ? C17 C12 C2 118.59(9) . . ? C14 C13 C12 120.08(10) . . ? C14 C13 H13 120.8(9) . . ? C12 C13 H13 119.1(9) . . ? C13 C14 C15 120.33(11) . . ? C13 C14 H14 120.6(10) . . ? C15 C14 H14 119.0(10) . . ? C16 C15 C14 120.39(11) . . ? C16 C15 H15 121.2(9) . . ? C14 C15 H15 118.4(9) . . ? C17 C16 C15 119.76(10) . . ? C17 C16 H16 118.9(9) . . ? C15 C16 H16 121.3(9) . . ? C16 C17 C12 120.53(10) . . ? C16 C17 H17 120.3(8) . . ? C12 C17 H17 119.2(8) . . ? O3 C18 H18C 108.2(12) . . ? O3 C18 H18B 111.9(13) . . ? H18C C18 H18B 112.3(17) . . ? O3 C18 H18A 110.7(13) . . ? H18C C18 H18A 108.3(17) . . ? H18B C18 H18A 105.4(18) . . ? O4 C19 H19A 107.5(11) . . ? O4 C19 H19B 112.5(12) . . ? H19A C19 H19B 111.5(16) . . ? O4 C19 H19C 108.6(13) . . ? H19A C19 H19C 109.5(17) . . ? H19B C19 H19C 107.2(18) . . ? C5 O1 C6 117.14(8) . . ? C3 O3 C18 114.04(11) . . ? C3 O4 C19 115.15(10) . . ? 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 C1 C2 C12 -3.8(2) . . . . ? C4 C1 C2 C12 179.73(13) . . . . ? C5 C1 C2 C3 176.33(13) . . . . ? C4 C1 C2 C3 -0.14(9) . . . . ? C1 C2 C3 O3 116.17(10) . . . . ? C12 C2 C3 O3 -63.71(14) . . . . ? C1 C2 C3 O4 -118.12(10) . . . . ? C12 C2 C3 O4 61.99(15) . . . . ? C1 C2 C3 C4 0.13(9) . . . . ? C12 C2 C3 C4 -179.76(11) . . . . ? C2 C1 C4 O5 179.40(17) . . . . ? C5 C1 C4 O5 2.8(3) . . . . ? C2 C1 C4 C3 0.13(9) . . . . ? C5 C1 C4 C3 -176.46(13) . . . . ? O3 C3 C4 O5 69.18(19) . . . . ? O4 C3 C4 O5 -61.9(2) . . . . ? C2 C3 C4 O5 -179.41(17) . . . . ? O3 C3 C4 C1 -111.53(10) . . . . ? O4 C3 C4 C1 117.38(10) . . . . ? C2 C3 C4 C1 -0.12(8) . . . . ? C2 C1 C5 O2 -22.3(2) . . . . ? C4 C1 C5 O2 152.96(14) . . . . ? C2 C1 C5 O1 159.92(13) . . . . ? C4 C1 C5 O1 -24.83(17) . . . . ? C11 C6 C7 C8 1.46(18) . . . . ? O1 C6 C7 C8 -174.58(10) . . . . ? C6 C7 C8 C9 -0.19(19) . . . . ? C7 C8 C9 C10 -1.25(19) . . . . ? C8 C9 C10 C11 1.46(19) . . . . ? C7 C6 C11 C10 -1.25(18) . . . . ? O1 C6 C11 C10 174.71(10) . . . . ? C9 C10 C11 C6 -0.23(18) . . . . ? C1 C2 C12 C13 5.2(2) . . . . ? C3 C2 C12 C13 -174.95(10) . . . . ? C1 C2 C12 C17 -175.00(13) . . . . ? C3 C2 C12 C17 4.83(16) . . . . ? C17 C12 C13 C14 -0.11(16) . . . . ? C2 C12 C13 C14 179.67(11) . . . . ? C12 C13 C14 C15 0.06(18) . . . . ? C13 C14 C15 C16 0.22(18) . . . . ? C14 C15 C16 C17 -0.44(18) . . . . ? C15 C16 C17 C12 0.39(17) . . . . ? C13 C12 C17 C16 -0.11(16) . . . . ? C2 C12 C17 C16 -179.90(10) . . . . ? O2 C5 O1 C6 2.98(18) . . . . ? C1 C5 O1 C6 -179.17(9) . . . . ? C7 C6 O1 C5 -108.96(12) . . . . ? C11 C6 O1 C5 74.90(13) . . . . ? O4 C3 O3 C18 64.20(13) . . . . ? C2 C3 O3 C18 -165.38(11) . . . . ? C4 C3 O3 C18 -71.24(13) . . . . ? O3 C3 O4 C19 -174.22(11) . . . . ? C2 C3 O4 C19 58.31(14) . . . . ? C4 C3 O4 C19 -39.52(14) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.252 _refine_diff_density_min -0.214 _refine_diff_density_rms 0.040