# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _publ_contact_author ; Botoshansky Mark Schulich Faculty of Chemistry, Technion-Israel Institute of Technology, 32000 Haifa, Israel ; _publ_contact_author-email botoshan@tx.technion.ac.il _publ_contact_author_fax +(972)48295703 _publ_contact_author_phone +(972)48293716 _publ_contact_author_letter ; Please consider this CIF submission for deposition. Full paper "Convergent Diastereoselective Preparation of Adjacent Quaternary Carbon Stereocenters in Acyclic System" by authors: T.Mejuch, B.Dutta M.Botoshansky and I.Marek will be send to J. Organic and Biomolecular Chemistry With regards M.Botoshansky ; _publ_contact_author_name 'Botoshansky, Mark' _publ_contact_author_email botoshan@tx.technion.ac.il loop_ _publ_author_name I.Marek T.Mejuch B.Dutta M.Botoshansky data_Marek-70 _database_code_depnum_ccdc_archive 'CCDC 861563' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Marek-70 (Bishnu)' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H26 O4' _chemical_formula_weight 306.39 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' 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 8.831(2) _cell_length_b 9.455(3) _cell_length_c 21.605(6) _cell_angle_alpha 90.00 _cell_angle_beta 99.620(8) _cell_angle_gamma 90.00 _cell_volume 1778.6(9) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 8431 _cell_measurement_theta_min 1.91 _cell_measurement_theta_max 24.78 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.144 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 664 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Nonius KappaCCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8431 _diffrn_reflns_av_R_equivalents 0.0810 _diffrn_reflns_av_sigmaI/netI 0.0555 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 24.78 _reflns_number_total 2565 _reflns_number_gt 1091 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius, 2006)' _computing_cell_refinement 'DENZO HKL2000 (Otwinowski & Minor 1997)' _computing_data_reduction 'DENZO HKL2000 (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'TEXSAN (MSC, 1999)' _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^)+(0.1599P)^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 SHELXL _refine_ls_extinction_coef 0.040(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2565 _refine_ls_number_parameters 200 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1610 _refine_ls_R_factor_gt 0.0795 _refine_ls_wR_factor_ref 0.2578 _refine_ls_wR_factor_gt 0.2151 _refine_ls_goodness_of_fit_ref 0.921 _refine_ls_restrained_S_all 0.954 _refine_ls_shift/su_max 0.010 _refine_ls_shift/su_mean 0.002 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 0.4873(4) -0.1048(3) 0.27479(13) 0.1291(12) Uani 1 1 d . . . H1 H 0.4228 -0.0448 0.2791 0.155 Uiso 1 1 d R . . O2 O 0.8432(4) 0.4670(3) 0.44367(15) 0.1298(12) Uani 1 1 d . . . O3 O 0.9940(4) 0.3184(3) 0.50388(17) 0.1343(13) Uani 1 1 d . . . H3 H 1.0323 0.3935 0.5176 0.161 Uiso 1 1 d R . . O4 O 0.2681(4) -0.0335(4) 0.34261(17) 0.1423(13) Uani 1 1 d . . . C1 C 0.4503(5) -0.2152(4) 0.3743(2) 0.1041(13) Uani 1 1 d . . . C2 C 0.5698(6) -0.1454(5) 0.3361(2) 0.1048(14) Uani 1 1 d . . . C3 C 0.6488(5) -0.0154(4) 0.3692(2) 0.0983(13) Uani 1 1 d . . . C4 C 0.6162(6) 0.1197(5) 0.3469(2) 0.1105(15) Uani 1 1 d . . . H4 H 0.5425 0.1322 0.3112 0.133 Uiso 1 1 calc R . . C5 C 0.6890(6) 0.2363(5) 0.3758(2) 0.1144(15) Uani 1 1 d . . . H5 H 0.6645 0.3260 0.3595 0.137 Uiso 1 1 calc R . . C6 C 0.7985(5) 0.2205(5) 0.4289(2) 0.1008(13) Uani 1 1 d . . . C7 C 0.8312(5) 0.0864(5) 0.4529(2) 0.1088(14) Uani 1 1 d . . . H7 H 0.9035 0.0744 0.4891 0.131 Uiso 1 1 calc R . . C8 C 0.7572(5) -0.0294(5) 0.4235(2) 0.1074(14) Uani 1 1 d . . . H8 H 0.7801 -0.1189 0.4403 0.129 Uiso 1 1 calc R . . C9 C 0.8809(6) 0.3439(5) 0.4598(2) 0.1082(14) Uani 1 1 d . . . C10 C 0.6871(6) -0.2516(5) 0.3218(3) 0.1341(17) Uani 1 1 d . . . H10A H 0.6353 -0.3327 0.3015 0.201 Uiso 1 1 calc R . . H10B H 0.7505 -0.2805 0.3603 0.201 Uiso 1 1 calc R . . H10C H 0.7499 -0.2092 0.2947 0.201 Uiso 1 1 calc R . . C11 C 0.3490(6) -0.1033(5) 0.3955(2) 0.1208(16) Uani 1 1 d . . . H11A H 0.2772 -0.1465 0.4192 0.145 Uiso 1 1 calc R . . H11B H 0.4112 -0.0359 0.4225 0.145 Uiso 1 1 calc R . . C12 C 0.1693(9) 0.0741(8) 0.3597(4) 0.211(3) Uani 1 1 d . . . H12A H 0.1179 0.1205 0.3225 0.316 Uiso 1 1 calc R . . H12B H 0.2290 0.1420 0.3864 0.316 Uiso 1 1 calc R . . H12C H 0.0946 0.0322 0.3816 0.316 Uiso 1 1 calc R . . C13 C 0.5355(6) -0.2956(5) 0.4312(3) 0.1274(17) Uani 1 1 d . . . H13 H 0.5968 -0.3700 0.4219 0.153 Uiso 1 1 calc R . . C14 C 0.5345(7) -0.2751(6) 0.4901(4) 0.156(2) Uani 1 1 d . . . H14A H 0.4757 -0.2025 0.5029 0.187 Uiso 1 1 calc R . . H14B H 0.5926 -0.3329 0.5199 0.187 Uiso 1 1 calc R . . C15 C 0.3517(6) -0.3270(5) 0.3336(2) 0.1243(17) Uani 1 1 d D . . H15A H 0.3051 -0.2818 0.2948 0.149 Uiso 1 1 calc R . . H15B H 0.4201 -0.3998 0.3228 0.149 Uiso 1 1 calc R . . C16 C 0.2279(7) -0.3974(6) 0.3608(3) 0.172(3) Uani 1 1 d D . . H16A H 0.1499 -0.3288 0.3667 0.206 Uiso 1 1 calc R . . H16B H 0.2697 -0.4373 0.4014 0.206 Uiso 1 1 calc R . . C17 C 0.1562(14) -0.5150(10) 0.3164(7) 0.300(7) Uani 1 1 d D . . H17A H 0.1785 -0.4915 0.2752 0.360 Uiso 1 1 calc R . . H17B H 0.2133 -0.6006 0.3295 0.360 Uiso 1 1 calc R . . C18 C 0.0045(14) -0.5507(14) 0.3082(7) 0.333(8) Uani 1 1 d D . . H18A H -0.0183 -0.6158 0.2738 0.500 Uiso 1 1 calc R . . H18B H -0.0570 -0.4671 0.2993 0.500 Uiso 1 1 calc R . . H18C H -0.0179 -0.5942 0.3458 0.500 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 0.156(3) 0.116(2) 0.110(2) -0.0043(16) 0.005(2) 0.004(2) O2 0.118(3) 0.097(2) 0.163(3) 0.0049(18) -0.011(2) 0.0190(18) O3 0.122(3) 0.100(2) 0.166(3) 0.0030(18) -0.018(2) 0.0042(18) O4 0.134(3) 0.124(2) 0.164(3) 0.001(2) 0.010(2) 0.040(2) C1 0.098(3) 0.097(3) 0.117(3) -0.007(2) 0.019(3) 0.008(3) C2 0.103(4) 0.107(3) 0.105(3) 0.004(2) 0.018(3) 0.011(3) C3 0.090(3) 0.094(3) 0.111(3) 0.002(2) 0.019(3) 0.003(2) C4 0.117(4) 0.095(3) 0.116(3) 0.009(3) 0.007(3) 0.003(3) C5 0.119(4) 0.097(3) 0.124(3) 0.017(3) 0.008(3) 0.016(3) C6 0.088(3) 0.096(3) 0.117(3) 0.004(2) 0.011(3) 0.011(2) C7 0.097(4) 0.101(3) 0.125(3) 0.010(3) 0.008(3) 0.016(3) C8 0.093(3) 0.092(3) 0.133(4) 0.013(2) 0.008(3) 0.009(3) C9 0.093(4) 0.103(4) 0.125(3) 0.007(3) 0.007(3) 0.023(3) C10 0.129(4) 0.119(4) 0.161(4) -0.011(3) 0.044(3) 0.016(3) C11 0.110(4) 0.110(3) 0.142(4) -0.006(3) 0.021(3) 0.009(3) C12 0.195(7) 0.187(6) 0.246(8) -0.015(5) 0.026(6) 0.096(6) C13 0.132(5) 0.114(4) 0.140(4) 0.004(3) 0.033(4) 0.005(3) C14 0.148(6) 0.155(5) 0.164(6) 0.019(4) 0.029(4) -0.002(4) C15 0.111(4) 0.106(3) 0.156(4) -0.018(3) 0.024(3) 0.002(3) C16 0.139(5) 0.123(4) 0.262(7) -0.031(4) 0.060(5) -0.032(4) C17 0.210(10) 0.183(7) 0.540(19) -0.172(10) 0.162(12) -0.087(7) C18 0.240(13) 0.331(15) 0.402(18) -0.149(13) -0.024(13) 0.048(12) _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 C2 1.453(5) . ? O1 H1 0.8200 . ? O2 C9 1.245(5) . ? O3 C9 1.283(5) . ? O3 H3 0.8200 . ? O4 C11 1.406(5) . ? O4 C12 1.428(6) . ? C1 C11 1.505(6) . ? C1 C13 1.531(7) . ? C1 C15 1.547(6) . ? C1 C2 1.588(6) . ? C2 C10 1.511(6) . ? C2 C3 1.530(6) . ? C3 C4 1.378(6) . ? C3 C8 1.392(6) . ? C4 C5 1.372(6) . ? C4 H4 0.9300 . ? C5 C6 1.380(6) . ? C5 H5 0.9300 . ? C6 C7 1.382(5) . ? C6 C9 1.474(6) . ? C7 C8 1.375(6) . ? C7 H7 0.9300 . ? C8 H8 0.9300 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 C14 1.289(7) . ? C13 H13 0.9300 . ? C14 H14A 0.9300 . ? C14 H14B 0.9300 . ? C15 C16 1.482(7) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.534(10) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C18 1.364(8) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? 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 O1 H1 109.4 . . ? C9 O3 H3 109.2 . . ? C11 O4 C12 112.0(4) . . ? C11 C1 C13 110.0(4) . . ? C11 C1 C15 110.3(4) . . ? C13 C1 C15 105.7(4) . . ? C11 C1 C2 110.3(4) . . ? C13 C1 C2 110.1(4) . . ? C15 C1 C2 110.4(4) . . ? O1 C2 C10 104.2(4) . . ? O1 C2 C3 109.5(3) . . ? C10 C2 C3 110.8(4) . . ? O1 C2 C1 108.0(4) . . ? C10 C2 C1 111.6(4) . . ? C3 C2 C1 112.5(3) . . ? C4 C3 C8 117.1(4) . . ? C4 C3 C2 122.0(4) . . ? C8 C3 C2 120.9(4) . . ? C3 C4 C5 122.2(4) . . ? C3 C4 H4 118.9 . . ? C5 C4 H4 118.9 . . ? C4 C5 C6 120.0(4) . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? C7 C6 C5 119.0(4) . . ? C7 C6 C9 120.0(4) . . ? C5 C6 C9 121.0(4) . . ? C8 C7 C6 120.3(4) . . ? C8 C7 H7 119.9 . . ? C6 C7 H7 119.9 . . ? C7 C8 C3 121.4(4) . . ? C7 C8 H8 119.3 . . ? C3 C8 H8 119.3 . . ? O2 C9 O3 121.5(4) . . ? O2 C9 C6 121.7(5) . . ? O3 C9 C6 116.9(4) . . ? C2 C10 H10A 109.5 . . ? C2 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C2 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? O4 C11 C1 109.3(4) . . ? O4 C11 H11A 109.8 . . ? C1 C11 H11A 109.8 . . ? O4 C11 H11B 109.8 . . ? C1 C11 H11B 109.8 . . ? H11A C11 H11B 108.3 . . ? O4 C12 H12A 109.5 . . ? O4 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? O4 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C14 C13 C1 129.4(5) . . ? C14 C13 H13 115.3 . . ? C1 C13 H13 115.3 . . ? C13 C14 H14A 120.0 . . ? C13 C14 H14B 120.0 . . ? H14A C14 H14B 120.0 . . ? C16 C15 C1 117.6(5) . . ? C16 C15 H15A 107.9 . . ? C1 C15 H15A 107.9 . . ? C16 C15 H15B 107.9 . . ? C1 C15 H15B 107.9 . . ? H15A C15 H15B 107.2 . . ? C15 C16 C17 109.4(6) . . ? C15 C16 H16A 109.8 . . ? C17 C16 H16A 109.8 . . ? C15 C16 H16B 109.8 . . ? C17 C16 H16B 109.8 . . ? H16A C16 H16B 108.2 . . ? C18 C17 C16 123.6(8) . . ? C18 C17 H17A 106.4 . . ? C16 C17 H17A 106.4 . . ? C18 C17 H17B 106.4 . . ? C16 C17 H17B 106.4 . . ? H17A C17 H17B 106.5 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? 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 C11 C1 C2 O1 -73.8(4) . . . . ? C13 C1 C2 O1 164.6(4) . . . . ? C15 C1 C2 O1 48.2(4) . . . . ? C11 C1 C2 C10 172.2(4) . . . . ? C13 C1 C2 C10 50.6(5) . . . . ? C15 C1 C2 C10 -65.7(5) . . . . ? C11 C1 C2 C3 47.0(5) . . . . ? C13 C1 C2 C3 -74.6(5) . . . . ? C15 C1 C2 C3 169.1(4) . . . . ? O1 C2 C3 C4 11.7(6) . . . . ? C10 C2 C3 C4 126.1(5) . . . . ? C1 C2 C3 C4 -108.3(5) . . . . ? O1 C2 C3 C8 -168.4(4) . . . . ? C10 C2 C3 C8 -54.1(5) . . . . ? C1 C2 C3 C8 71.6(5) . . . . ? C8 C3 C4 C5 1.5(7) . . . . ? C2 C3 C4 C5 -178.7(4) . . . . ? C3 C4 C5 C6 -0.2(7) . . . . ? C4 C5 C6 C7 -1.1(7) . . . . ? C4 C5 C6 C9 178.5(4) . . . . ? C5 C6 C7 C8 1.0(7) . . . . ? C9 C6 C7 C8 -178.5(4) . . . . ? C6 C7 C8 C3 0.3(7) . . . . ? C4 C3 C8 C7 -1.5(7) . . . . ? C2 C3 C8 C7 178.7(4) . . . . ? C7 C6 C9 O2 -172.1(5) . . . . ? C5 C6 C9 O2 8.3(7) . . . . ? C7 C6 C9 O3 8.2(7) . . . . ? C5 C6 C9 O3 -171.3(4) . . . . ? C12 O4 C11 C1 179.9(5) . . . . ? C13 C1 C11 O4 -178.2(4) . . . . ? C15 C1 C11 O4 -61.9(5) . . . . ? C2 C1 C11 O4 60.2(5) . . . . ? C11 C1 C13 C14 -3.1(8) . . . . ? C15 C1 C13 C14 -122.2(6) . . . . ? C2 C1 C13 C14 118.6(6) . . . . ? C11 C1 C15 C16 -54.7(6) . . . . ? C13 C1 C15 C16 64.2(6) . . . . ? C2 C1 C15 C16 -176.8(4) . . . . ? C1 C15 C16 C17 -173.8(7) . . . . ? C15 C16 C17 C18 -145.7(15) . . . . ? loop_ # start Validation Reply Form _vrf_PLAT022_Marek-70 ; PROBLEM: Ratio Unique/Expected Reflections too Low..0.84 RESPONSE: Very weak diffracted crystals ; _vrf_PLAT029_Marek-70 ; PROBLEM: _diffrn_measured_fraction_theta_full Low .. 0.84 RESPONSE: Very weak diffracted crystals ; # end Validation Reply Form _diffrn_measured_fraction_theta_max 0.840 _diffrn_reflns_theta_full 24.78 _diffrn_measured_fraction_theta_full 0.840 _refine_diff_density_max 0.305 _refine_diff_density_min -0.223 _refine_diff_density_rms 0.045 data_Marek-88 _database_code_depnum_ccdc_archive 'CCDC 861564' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Marek-88 ( Tom)' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H24 O4' _chemical_formula_weight 292.36 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.032(1) _cell_length_b 9.304(1) _cell_length_c 11.542(1) _cell_angle_alpha 103.644(4) _cell_angle_beta 92.877(4) _cell_angle_gamma 97.279(3) _cell_volume 828.56(15) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.172 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 316 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9585 _exptl_absorpt_correction_T_max 0.9789 _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 APEX2 DUO' _diffrn_measurement_method \w-scan _diffrn_detector_area_resol_mean 8.3333 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% ? _diffrn_reflns_number 3930 _diffrn_reflns_av_R_equivalents 0.0221 _diffrn_reflns_av_sigmaI/netI 0.0395 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 25.10 _reflns_number_total 2919 _reflns_number_gt 2185 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Instrument Service v2010.7.0.0' _computing_cell_refinement 'APEX2 v2010.7-0 (Bruker AXS)' _computing_data_reduction 'SAINT V7.68A (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.1051P)^2^+0.1545P] 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 SHELXL _refine_ls_extinction_coef 0.063(14) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2919 _refine_ls_number_parameters 196 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0773 _refine_ls_R_factor_gt 0.0599 _refine_ls_wR_factor_ref 0.1958 _refine_ls_wR_factor_gt 0.1827 _refine_ls_goodness_of_fit_ref 1.116 _refine_ls_restrained_S_all 1.116 _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 0.2080(2) 0.00633(19) 0.48423(15) 0.0660(5) Uani 1 1 d . . . O2 O 0.0098(2) 0.0634(2) 0.36818(15) 0.0667(5) Uani 1 1 d . . . H2 H -0.0506 0.0355 0.4161 0.100 Uiso 1 1 calc R . . O3 O 0.82066(18) 0.23007(15) 0.13251(14) 0.0550(4) Uani 1 1 d . . . O4 O 0.6058(2) 0.55349(16) 0.22250(14) 0.0607(5) Uani 1 1 d . . . C1 C 0.6768(2) 0.3090(2) 0.13717(18) 0.0461(5) Uani 1 1 d . . . C2 C 0.5400(2) 0.2359(2) 0.20075(17) 0.0433(5) Uani 1 1 d . . . C3 C 0.3705(3) 0.2482(2) 0.17907(18) 0.0488(5) Uani 1 1 d . . . H3 H 0.3395 0.2972 0.1216 0.059 Uiso 1 1 calc R . . C4 C 0.2480(3) 0.1890(2) 0.24121(19) 0.0498(5) Uani 1 1 d . . . H4 H 0.1357 0.1986 0.2257 0.060 Uiso 1 1 calc R . . C5 C 0.2928(3) 0.1152(2) 0.32693(17) 0.0471(5) Uani 1 1 d . . . C6 C 0.4597(3) 0.1000(2) 0.3476(2) 0.0540(6) Uani 1 1 d . . . H6 H 0.4902 0.0498 0.4043 0.065 Uiso 1 1 calc R . . C7 C 0.5815(3) 0.1587(2) 0.2848(2) 0.0524(5) Uani 1 1 d . . . H7 H 0.6931 0.1464 0.2991 0.063 Uiso 1 1 calc R . . C8 C 0.1640(3) 0.0561(2) 0.39817(19) 0.0507(5) Uani 1 1 d . . . C9 C 0.6120(3) 0.3119(3) 0.0114(2) 0.0602(6) Uani 1 1 d . . . H9A H 0.7051 0.3381 -0.0322 0.090 Uiso 1 1 calc R . . H9B H 0.5359 0.3844 0.0163 0.090 Uiso 1 1 calc R . . H9C H 0.5540 0.2149 -0.0292 0.090 Uiso 1 1 calc R . . C10 C 0.7963(4) 0.0837(3) 0.0572(3) 0.0794(8) Uani 1 1 d . . . H10A H 0.6902 0.0316 0.0698 0.119 Uiso 1 1 calc R . . H10B H 0.8856 0.0311 0.0758 0.119 Uiso 1 1 calc R . . H10C H 0.7965 0.0890 -0.0248 0.119 Uiso 1 1 calc R . . C11 C 0.7469(3) 0.4728(2) 0.21222(19) 0.0511(5) Uani 1 1 d . . . C12 C 0.8376(4) 0.4726(3) 0.3319(2) 0.0696(7) Uani 1 1 d . . . H12A H 0.7554 0.4369 0.3812 0.084 Uiso 1 1 calc R . . H12B H 0.9179 0.4020 0.3170 0.084 Uiso 1 1 calc R . . C13 C 0.9307(4) 0.6236(3) 0.4021(3) 0.0996(11) Uani 1 1 d . . . H13A H 1.0350 0.6445 0.3680 0.149 Uiso 1 1 calc R . . H13B H 0.9534 0.6211 0.4840 0.149 Uiso 1 1 calc R . . H13C H 0.8624 0.7001 0.3984 0.149 Uiso 1 1 calc R . . C14 C 0.8700(3) 0.5448(3) 0.1401(2) 0.0673(7) Uani 1 1 d . . . H14 H 0.9584 0.4934 0.1135 0.081 Uiso 1 1 calc R . . C15 C 0.8639(4) 0.6707(3) 0.1119(3) 0.0923(10) Uani 1 1 d . . . H15A H 0.7778 0.7261 0.1365 0.111 Uiso 1 1 calc R . . H15B H 0.9456 0.7059 0.0671 0.111 Uiso 1 1 calc R . . C16 C 0.5306(4) 0.5899(4) 0.3319(3) 0.0951(10) Uani 1 1 d . . . H16A H 0.6119 0.6544 0.3932 0.114 Uiso 1 1 calc R . . H16B H 0.4943 0.4996 0.3574 0.114 Uiso 1 1 calc R . . C17 C 0.3865(5) 0.6657(5) 0.3155(3) 0.1219(14) Uani 1 1 d . . . H17A H 0.4235 0.7556 0.2914 0.183 Uiso 1 1 calc R . . H17B H 0.3346 0.6902 0.3894 0.183 Uiso 1 1 calc R . . H17C H 0.3064 0.6012 0.2549 0.183 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 0.0624(10) 0.0779(11) 0.0711(11) 0.0382(9) 0.0212(8) 0.0166(8) O2 0.0520(10) 0.0867(12) 0.0679(11) 0.0318(9) 0.0159(8) 0.0053(8) O3 0.0495(9) 0.0498(8) 0.0635(10) 0.0059(7) 0.0146(7) 0.0096(6) O4 0.0664(10) 0.0561(9) 0.0630(10) 0.0135(7) 0.0168(8) 0.0195(7) C1 0.0434(11) 0.0489(11) 0.0459(11) 0.0107(9) 0.0093(8) 0.0061(9) C2 0.0456(11) 0.0417(10) 0.0418(10) 0.0080(8) 0.0078(8) 0.0055(8) C3 0.0480(12) 0.0533(11) 0.0462(11) 0.0163(9) 0.0017(9) 0.0044(9) C4 0.0424(11) 0.0542(11) 0.0510(12) 0.0112(9) 0.0045(9) 0.0028(9) C5 0.0493(12) 0.0452(10) 0.0464(11) 0.0102(9) 0.0108(9) 0.0049(9) C6 0.0557(12) 0.0583(12) 0.0570(13) 0.0277(10) 0.0122(10) 0.0137(10) C7 0.0456(12) 0.0582(12) 0.0593(13) 0.0227(10) 0.0081(10) 0.0119(9) C8 0.0543(13) 0.0479(11) 0.0498(12) 0.0103(9) 0.0151(10) 0.0063(9) C9 0.0616(14) 0.0692(14) 0.0489(13) 0.0168(10) 0.0095(10) -0.0010(11) C10 0.0743(17) 0.0587(14) 0.098(2) -0.0020(14) 0.0277(15) 0.0133(13) C11 0.0505(12) 0.0456(11) 0.0552(12) 0.0091(9) 0.0070(9) 0.0047(9) C12 0.0767(17) 0.0636(14) 0.0601(14) 0.0023(11) -0.0122(12) 0.0097(12) C13 0.093(2) 0.084(2) 0.098(2) -0.0153(17) -0.0275(19) 0.0126(17) C14 0.0550(14) 0.0584(13) 0.0850(18) 0.0138(12) 0.0148(12) -0.0017(11) C15 0.089(2) 0.0809(19) 0.119(3) 0.0481(18) 0.0285(18) 0.0018(16) C16 0.082(2) 0.111(2) 0.082(2) -0.0079(17) 0.0164(16) 0.0270(18) C17 0.113(3) 0.153(3) 0.105(3) 0.008(2) 0.034(2) 0.070(3) _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 C8 1.245(2) . ? O2 C8 1.283(3) . ? O2 H2 0.8200 . ? O3 C10 1.416(3) . ? O3 C1 1.442(2) . ? O4 C16 1.414(3) . ? O4 C11 1.431(3) . ? C1 C9 1.525(3) . ? C1 C2 1.529(3) . ? C1 C11 1.582(3) . ? C2 C7 1.387(3) . ? C2 C3 1.395(3) . ? C3 C4 1.380(3) . ? C3 H3 0.9300 . ? C4 C5 1.388(3) . ? C4 H4 0.9300 . ? C5 C6 1.380(3) . ? C5 C8 1.484(3) . ? C6 C7 1.379(3) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C14 1.515(3) . ? C11 C12 1.530(3) . ? C12 C13 1.525(4) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 C15 1.294(4) . ? C14 H14 0.9300 . ? C15 H15A 0.9300 . ? C15 H15B 0.9300 . ? C16 C17 1.456(4) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? 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 C8 O2 H2 109.5 . . ? C10 O3 C1 115.65(17) . . ? C16 O4 C11 120.8(2) . . ? O3 C1 C9 110.33(17) . . ? O3 C1 C2 109.60(15) . . ? C9 C1 C2 111.40(17) . . ? O3 C1 C11 104.37(15) . . ? C9 C1 C11 110.16(17) . . ? C2 C1 C11 110.76(16) . . ? C7 C2 C3 117.88(18) . . ? C7 C2 C1 120.75(18) . . ? C3 C2 C1 121.34(16) . . ? C4 C3 C2 121.31(18) . . ? C4 C3 H3 119.3 . . ? C2 C3 H3 119.3 . . ? C3 C4 C5 119.84(19) . . ? C3 C4 H4 120.1 . . ? C5 C4 H4 120.1 . . ? C6 C5 C4 119.33(18) . . ? C6 C5 C8 119.97(18) . . ? C4 C5 C8 120.69(18) . . ? C7 C6 C5 120.59(18) . . ? C7 C6 H6 119.7 . . ? C5 C6 H6 119.7 . . ? C6 C7 C2 121.02(19) . . ? C6 C7 H7 119.5 . . ? C2 C7 H7 119.5 . . ? O1 C8 O2 123.20(19) . . ? O1 C8 C5 120.04(19) . . ? O2 C8 C5 116.73(18) . . ? C1 C9 H9A 109.5 . . ? C1 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C1 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O3 C10 H10A 109.5 . . ? O3 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? O3 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? O4 C11 C14 107.15(17) . . ? O4 C11 C12 114.38(19) . . ? C14 C11 C12 108.9(2) . . ? O4 C11 C1 106.01(16) . . ? C14 C11 C1 108.47(18) . . ? C12 C11 C1 111.72(17) . . ? C13 C12 C11 115.2(2) . . ? C13 C12 H12A 108.5 . . ? C11 C12 H12A 108.5 . . ? C13 C12 H12B 108.5 . . ? C11 C12 H12B 108.5 . . ? H12A C12 H12B 107.5 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C15 C14 C11 126.2(3) . . ? C15 C14 H14 116.9 . . ? C11 C14 H14 116.9 . . ? C14 C15 H15A 120.0 . . ? C14 C15 H15B 120.0 . . ? H15A C15 H15B 120.0 . . ? O4 C16 C17 109.1(3) . . ? O4 C16 H16A 109.9 . . ? C17 C16 H16A 109.9 . . ? O4 C16 H16B 109.9 . . ? C17 C16 H16B 109.9 . . ? H16A C16 H16B 108.3 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? 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 O3 C1 C9 -54.3(2) . . . . ? C10 O3 C1 C2 68.7(2) . . . . ? C10 O3 C1 C11 -172.65(19) . . . . ? O3 C1 C2 C7 27.0(3) . . . . ? C9 C1 C2 C7 149.4(2) . . . . ? C11 C1 C2 C7 -87.6(2) . . . . ? O3 C1 C2 C3 -154.94(18) . . . . ? C9 C1 C2 C3 -32.5(3) . . . . ? C11 C1 C2 C3 90.4(2) . . . . ? C7 C2 C3 C4 1.6(3) . . . . ? C1 C2 C3 C4 -176.45(18) . . . . ? C2 C3 C4 C5 -0.2(3) . . . . ? C3 C4 C5 C6 -1.0(3) . . . . ? C3 C4 C5 C8 177.53(18) . . . . ? C4 C5 C6 C7 0.7(3) . . . . ? C8 C5 C6 C7 -177.84(19) . . . . ? C5 C6 C7 C2 0.8(3) . . . . ? C3 C2 C7 C6 -1.9(3) . . . . ? C1 C2 C7 C6 176.16(19) . . . . ? C6 C5 C8 O1 7.1(3) . . . . ? C4 C5 C8 O1 -171.35(19) . . . . ? C6 C5 C8 O2 -174.71(19) . . . . ? C4 C5 C8 O2 6.8(3) . . . . ? C16 O4 C11 C14 -138.1(2) . . . . ? C16 O4 C11 C12 -17.4(3) . . . . ? C16 O4 C11 C1 106.2(2) . . . . ? O3 C1 C11 O4 -177.97(14) . . . . ? C9 C1 C11 O4 63.6(2) . . . . ? C2 C1 C11 O4 -60.1(2) . . . . ? O3 C1 C11 C14 67.2(2) . . . . ? C9 C1 C11 C14 -51.2(2) . . . . ? C2 C1 C11 C14 -174.90(17) . . . . ? O3 C1 C11 C12 -52.8(2) . . . . ? C9 C1 C11 C12 -171.19(19) . . . . ? C2 C1 C11 C12 65.1(2) . . . . ? O4 C11 C12 C13 -68.0(3) . . . . ? C14 C11 C12 C13 51.9(3) . . . . ? C1 C11 C12 C13 171.6(2) . . . . ? O4 C11 C14 C15 11.4(4) . . . . ? C12 C11 C14 C15 -112.7(3) . . . . ? C1 C11 C14 C15 125.5(3) . . . . ? C11 O4 C16 C17 -177.6(3) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 25.10 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.392 _refine_diff_density_min -0.255 _refine_diff_density_rms 0.044