Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2002 data_global _publ_contact_author_email crvalero@icmm.csic.es _publ_contact_author_name 'Dr Caridad Ruiz-Valero' _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name J.Perles M.Iglesias C.Ruiz-Valero N.Snejko data_jpsc11 _database_code_CSD 196089 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C10 H11 O11 Sc2' _chemical_formula_weight 397.11 _chemical_melting_point ? _chemical_compound_source ? 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' Sc Sc 0.2519 0.3716 '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)/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 9.196(2) _cell_length_b 7.857(2) _cell_length_c 19.894(5) _cell_angle_alpha 90.00 _cell_angle_beta 95.948(5) _cell_angle_gamma 90.00 _cell_volume 1429.6(6) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'hexagonal prism' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.845 _exptl_crystal_density_method ? _exptl_crystal_F_000 804 _exptl_absorpt_coefficient_mu 1.007 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'Smart CCD Bruker' _diffrn_measurement_method 'phi and omega scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 7566 _diffrn_reflns_av_R_equivalents 0.1970 _diffrn_reflns_av_sigmaI/netI 0.4897 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 3.87 _diffrn_reflns_theta_max 30.92 _reflns_number_total 3547 _reflns_number_observed 1023 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0400P)^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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3547 _refine_ls_number_parameters 206 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2860 _refine_ls_R_factor_obs 0.0677 _refine_ls_wR_factor_all 0.1609 _refine_ls_wR_factor_obs 0.1108 _refine_ls_goodness_of_fit_all 0.729 _refine_ls_goodness_of_fit_obs 0.999 _refine_ls_restrained_S_all 0.729 _refine_ls_restrained_S_obs 0.999 _refine_ls_shift/esd_max -3.598 _refine_ls_shift/esd_mean 0.265 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Sc1 Sc 0.20316(15) 0.6849(2) 0.14829(7) 0.0198(4) Uani 1 d . . Sc2 Sc -0.18554(14) 0.6874(2) 0.17095(7) 0.0215(4) Uani 1 d . . O1 O 0.0846(5) 0.7501(7) 0.0554(2) 0.035(2) Uani 1 d . . O2 O -0.1520(5) 0.7527(7) 0.0705(3) 0.037(2) Uani 1 d . . O3 O 0.1070(5) 0.4468(7) 0.1324(3) 0.035(2) Uani 1 d . . O4 O -0.1277(6) 0.4349(7) 0.1440(3) 0.044(2) Uani 1 d . . O5 O 0.2984(5) 0.9294(7) 0.1553(3) 0.0312(15) Uani 1 d . . O6 O -0.2174(5) 0.5857(7) 0.2646(3) 0.036(2) Uani 1 d . . O7 O 0.3232(5) 0.6131(7) 0.2362(3) 0.035(2) Uani 1 d . . O8 O -0.2511(6) 0.9327(7) 0.1885(3) 0.042(2) Uani 1 d . . O9 O 0.3689(5) 0.6009(7) 0.0933(3) 0.0307(15) Uani 1 d . . O10 O -0.4048(5) 0.6344(7) 0.1390(3) 0.034(2) Uani 1 d . . O11 O 0.0295(5) 0.7569(6) 0.2001(3) 0.0245(14) Uani 1 d . . C1 C -0.0501(9) 0.7675(9) 0.0340(4) 0.020(2) Uani 1 d . . C2 C -0.0942(7) 0.8173(10) -0.0386(3) 0.022(2) Uani 1 d . . H2A H -0.1237(7) 0.9359(10) -0.0394(3) 0.027 Uiso 1 calc R . H2B H -0.1792(7) 0.7507(10) -0.0551(3) 0.027 Uiso 1 calc R . C3 C 0.0220(7) 0.7951(9) -0.0880(4) 0.021(2) Uani 1 d . . H3A H 0.0096(7) 0.8841(9) -0.1219(4) 0.025 Uiso 1 calc R . H3B H 0.1181(7) 0.8087(9) -0.0635(4) 0.025 Uiso 1 calc R . C4 C -0.0151(9) 0.3745(10) 0.1229(4) 0.020(2) Uani 1 d . . C5 C 0.3072(8) 1.0563(11) 0.1927(4) 0.023(2) Uani 1 d . . C6 C 0.4190(7) 1.1924(10) 0.1814(4) 0.024 Uani 1 d . . H6A H 0.4463(7) 1.2498(10) 0.2240(4) 0.028 Uiso 1 calc R . H6B H 0.3732(7) 1.2760(10) 0.1501(4) 0.028 Uiso 1 calc R . C7 C 0.5583(7) 1.1280(10) 0.1537(4) 0.029(2) Uani 1 d . . H7A H 0.5313(7) 1.0448(10) 0.1186(4) 0.035 Uiso 1 calc R . H7B H 0.6047(7) 1.2227(10) 0.1330(4) 0.035 Uiso 1 calc R . C8 C 0.3333(8) 0.5490(11) 0.2942(4) 0.020(2) Uani 1 d . . C9 C -0.4943(8) 0.5939(10) 0.0905(4) 0.025(2) Uani 1 d . . C10 C -0.4410(7) 0.5350(11) 0.0258(4) 0.035(2) Uani 1 d . . H10A H -0.3678(7) 0.4474(11) 0.0361(4) 0.042 Uiso 1 calc R . H10B H -0.3937(7) 0.6298(11) 0.0056(4) 0.042 Uiso 1 calc R . H11 H 0.0429(72) 0.8199(82) 0.2415(36) 0.078(24) Uiso 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 Sc1 0.0077(8) 0.0281(10) 0.0238(9) -0.0036(8) 0.0019(7) -0.0016(7) Sc2 0.0102(8) 0.0309(10) 0.0243(9) -0.0011(8) 0.0067(7) -0.0012(7) O1 0.020(3) 0.056(4) 0.029(4) 0.009(3) 0.005(3) 0.006(3) O2 0.020(3) 0.066(5) 0.025(3) 0.004(3) 0.011(3) -0.010(3) O3 0.019(3) 0.027(4) 0.061(4) -0.016(3) 0.009(3) 0.001(3) O4 0.019(3) 0.050(5) 0.066(5) -0.015(4) 0.016(3) 0.003(3) O5 0.021(3) 0.033(4) 0.041(4) -0.009(3) 0.014(3) -0.007(3) O6 0.023(3) 0.050(4) 0.039(4) 0.009(3) 0.016(3) -0.003(3) O7 0.022(3) 0.056(4) 0.028(4) 0.010(3) 0.008(3) 0.001(3) O8 0.030(4) 0.030(4) 0.067(5) -0.003(3) 0.008(3) 0.011(3) O9 0.010(3) 0.048(4) 0.036(4) -0.009(3) 0.011(3) 0.000(3) O10 0.011(3) 0.070(5) 0.020(3) -0.012(3) 0.004(3) -0.008(3) O11 0.008(3) 0.044(4) 0.022(3) -0.011(3) 0.008(2) -0.005(2) C1 0.025(5) 0.010(5) 0.025(5) -0.003(4) 0.004(4) -0.002(4) C2 0.019(4) 0.022(5) 0.026(5) 0.000(4) 0.003(4) 0.011(4) C3 0.018(4) 0.017(5) 0.027(5) -0.008(4) -0.004(4) -0.002(4) C4 0.020(5) 0.025(5) 0.015(5) 0.005(4) -0.003(4) -0.001(4) C5 0.015(5) 0.027(5) 0.026(5) 0.000(4) -0.008(4) -0.002(4) C6 0.004 0.030 0.036 0.005 0.000 0.007 C7 0.023(5) 0.043(6) 0.022(5) 0.007(4) 0.005(4) -0.006(4) C8 0.004(4) 0.027(5) 0.030(6) 0.007(5) 0.006(4) 0.005(4) C9 0.018(5) 0.023(5) 0.034(6) 0.006(4) 0.007(4) 0.001(4) C10 0.015(5) 0.049(6) 0.040(6) -0.026(5) 0.002(4) -0.003(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 Sc1 O7 2.048(5) . ? Sc1 O9 2.074(5) . ? Sc1 O11 2.067(5) . ? Sc1 O3 2.080(5) . ? Sc1 O5 2.110(6) . ? Sc1 O1 2.110(5) . ? Sc1 Sc2 3.649(2) . ? Sc2 O8 2.060(6) . ? Sc2 O6 2.076(6) . ? Sc2 O11 2.076(5) . ? Sc2 O10 2.092(5) . ? Sc2 O2 2.117(5) . ? Sc2 O4 2.137(6) . ? O1 C1 1.274(8) . ? O2 C1 1.248(8) . ? O3 C4 1.254(8) . ? O4 C4 1.251(8) . ? O5 C5 1.241(9) . ? O6 C5 1.266(8) 2_545 ? O7 C8 1.254(8) . ? O8 C8 1.256(8) 2 ? O9 C9 1.266(8) 1_655 ? O10 C9 1.243(8) . ? C1 C2 1.511(9) . ? C2 C3 1.535(9) . ? C3 C4 1.500(9) 3_565 ? C4 C3 1.500(9) 3_565 ? C5 O6 1.266(8) 2 ? C5 C6 1.516(10) . ? C6 C7 1.532(9) . ? C7 C8 1.496(10) 2_655 ? C8 O8 1.256(8) 2_545 ? C8 C7 1.496(10) 2_645 ? C9 O9 1.266(8) 1_455 ? C9 C10 1.498(10) . ? C10 C10 1.517(12) 3_465 ? 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 O7 Sc1 O9 90.1(2) . . ? O7 Sc1 O11 91.5(2) . . ? O9 Sc1 O11 176.4(2) . . ? O7 Sc1 O3 93.7(2) . . ? O9 Sc1 O3 87.6(2) . . ? O11 Sc1 O3 89.1(2) . . ? O7 Sc1 O5 90.6(2) . . ? O9 Sc1 O5 90.1(2) . . ? O11 Sc1 O5 93.1(2) . . ? O3 Sc1 O5 175.1(2) . . ? O7 Sc1 O1 177.3(2) . . ? O9 Sc1 O1 87.5(2) . . ? O11 Sc1 O1 90.8(2) . . ? O3 Sc1 O1 85.0(2) . . ? O5 Sc1 O1 90.6(2) . . ? O7 Sc1 Sc2 110.12(15) . . ? O9 Sc1 Sc2 148.2(2) . . ? O11 Sc1 Sc2 28.32(14) . . ? O3 Sc1 Sc2 67.48(14) . . ? O5 Sc1 Sc2 113.08(15) . . ? O1 Sc1 Sc2 71.52(14) . . ? O8 Sc2 O6 97.9(2) . . ? O8 Sc2 O11 89.6(2) . . ? O6 Sc2 O11 94.0(2) . . ? O8 Sc2 O10 87.0(2) . . ? O6 Sc2 O10 88.5(2) . . ? O11 Sc2 O10 176.1(2) . . ? O8 Sc2 O2 90.4(2) . . ? O6 Sc2 O2 171.4(2) . . ? O11 Sc2 O2 88.4(2) . . ? O10 Sc2 O2 89.5(2) . . ? O8 Sc2 O4 174.9(2) . . ? O6 Sc2 O4 86.0(2) . . ? O11 Sc2 O4 93.4(2) . . ? O10 Sc2 O4 89.7(2) . . ? O2 Sc2 O4 85.6(2) . . ? O8 Sc2 Sc1 109.5(2) . . ? O6 Sc2 Sc1 109.87(15) . . ? O11 Sc2 Sc1 28.19(14) . . ? O10 Sc2 Sc1 152.50(15) . . ? O2 Sc2 Sc1 69.17(14) . . ? O4 Sc2 Sc1 72.03(15) . . ? C1 O1 Sc1 135.6(5) . . ? C1 O2 Sc2 139.7(5) . . ? C4 O3 Sc1 142.2(5) . . ? C4 O4 Sc2 132.3(5) . . ? C5 O5 Sc1 140.5(6) . . ? C5 O6 Sc2 146.7(5) 2_545 . ? C8 O7 Sc1 151.5(5) . . ? C8 O8 Sc2 157.2(6) 2 . ? C9 O9 Sc1 145.5(6) 1_655 . ? C9 O10 Sc2 145.7(5) . . ? Sc1 O11 Sc2 123.5(3) . . ? O2 C1 O1 124.0(7) . . ? O2 C1 C2 115.9(7) . . ? O1 C1 C2 120.1(7) . . ? C1 C2 C3 116.6(6) . . ? C4 C3 C2 113.5(6) 3_565 . ? O4 C4 O3 122.4(8) . . ? O4 C4 C3 119.7(7) . 3_565 ? O3 C4 C3 117.8(7) . 3_565 ? O5 C5 O6 122.8(8) . 2 ? O5 C5 C6 118.8(8) . . ? O6 C5 C6 118.0(7) 2 . ? C5 C6 C7 115.2(7) . . ? C8 C7 C6 114.2(6) 2_655 . ? O7 C8 O8 123.6(8) . 2_545 ? O7 C8 C7 116.9(7) . 2_645 ? O8 C8 C7 119.3(8) 2_545 2_645 ? O10 C9 O9 122.4(8) . 1_455 ? O10 C9 C10 119.8(7) . . ? O9 C9 C10 117.7(7) 1_455 . ? C9 C10 C10 114.8(8) . 3_465 ? _refine_diff_density_max 0.541 _refine_diff_density_min -0.520 _refine_diff_density_rms 0.117