# Supplementary Material (ESI) for Green Chemistry # This journal is © The Royal Society of Chemistry 2004 data_global _journal_coden_Cambridge 1048 loop_ _publ_author_name 'Alison Stuart' 'John Fawcett' 'Eric Hope' 'Andrew West' _publ_contact_author_name 'Dr Alison Stuart' _publ_contact_author_address ; Department of Chemistry University of Leicester University Road Leicester Leicestershire LE1 7RH UNITED KINGDOM ; _publ_contact_author_email AMC17@LE.AC.UK _publ_requested_journal 'Green Chemistry' _publ_section_title ; Recycling of a perfluoroalkylated BINOL ligand using fluorous solid-phase extraction ; data_04004 _database_code_depnum_ccdc_archive 'CCDC 257732' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H40 O2 Sn' _chemical_formula_weight 575.33 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' Sn Sn -0.6537 1.4246 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 11.2787(12) _cell_length_b 11.6990(13) _cell_length_c 11.6960(13) _cell_angle_alpha 90.00 _cell_angle_beta 115.519(2) _cell_angle_gamma 90.00 _cell_volume 1392.7(3) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 7853 _cell_measurement_theta_min 2.60 _cell_measurement_theta_max 28.12 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.372 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 596 _exptl_absorpt_coefficient_mu 0.943 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.802 _exptl_absorpt_correction_T_max 0.928 _exptl_absorpt_process_details ; absorption correction based on 9841 reflections (SADABS); Rint 0.036 before correction and 0.030 after. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10765 _diffrn_reflns_av_R_equivalents 0.0232 _diffrn_reflns_av_sigmaI/netI 0.0354 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 25.99 _reflns_number_total 5207 _reflns_number_gt 5031 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; The highest residual electron density peak was 3.9e at 1.1A from the Sn atom. The residual peak was present with both the empirical absorption correction and an analytical correction based on face index measurements. 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^)+(0.0905P)^2^+0.3404P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.02(3) _refine_ls_number_reflns 5207 _refine_ls_number_parameters 317 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0459 _refine_ls_R_factor_gt 0.0450 _refine_ls_wR_factor_ref 0.1205 _refine_ls_wR_factor_gt 0.1199 _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_restrained_S_all 1.076 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Sn1 Sn 0.09564(2) 0.87379(5) 0.49311(2) 0.01679(11) Uani 1 1 d . . . O1 O -0.0531(4) 0.5809(3) 0.5814(3) 0.0215(8) Uani 1 1 d . . . O2 O 0.1214(4) 0.7026(3) 0.5647(3) 0.0207(8) Uani 1 1 d . . . C1 C -0.0787(6) 0.8297(5) 0.3288(5) 0.0232(11) Uani 1 1 d . . . H1A H -0.0936 0.8885 0.2656 0.028 Uiso 1 1 calc R . . H1B H -0.0615 0.7590 0.2951 0.028 Uiso 1 1 calc R . . C2 C -0.2068(6) 0.8140(5) 0.3427(6) 0.0305(13) Uani 1 1 d . . . H2A H -0.1912 0.7633 0.4134 0.037 Uiso 1 1 calc R . . H2B H -0.2348 0.8874 0.3612 0.037 Uiso 1 1 calc R . . C3 C -0.3149(6) 0.7649(5) 0.2235(6) 0.0328(14) Uani 1 1 d . . . H3A H -0.3273 0.8146 0.1529 0.039 Uiso 1 1 calc R . . H3B H -0.2867 0.6910 0.2068 0.039 Uiso 1 1 calc R . . C4 C -0.4451(6) 0.7506(7) 0.2296(7) 0.0458(19) Uani 1 1 d . . . H4A H -0.4311 0.7160 0.3088 0.069 Uiso 1 1 d R . . H4B H -0.5015 0.7027 0.1611 0.069 Uiso 1 1 d R . . H4C H -0.4855 0.8241 0.2227 0.069 Uiso 1 1 d R . . C5 C 0.1040(6) 0.9515(5) 0.6622(5) 0.0224(11) Uani 1 1 d . . . H5A H 0.1558 0.9030 0.7337 0.027 Uiso 1 1 calc R . . H5B H 0.1492 1.0241 0.6745 0.027 Uiso 1 1 calc R . . C6 C -0.0285(6) 0.9719(5) 0.6625(5) 0.0240(12) Uani 1 1 d . . . H6A H -0.0731 0.8993 0.6536 0.029 Uiso 1 1 calc R . . H6B H -0.0817 1.0190 0.5902 0.029 Uiso 1 1 calc R . . C7 C -0.0163(6) 1.0307(5) 0.7838(6) 0.0259(12) Uani 1 1 d . . . H7A H 0.0313 0.9811 0.8556 0.031 Uiso 1 1 calc R . . H7B H 0.0338 1.1007 0.7959 0.031 Uiso 1 1 calc R . . C8 C -0.1479(8) 1.0583(7) 0.7795(8) 0.0373(19) Uani 1 1 d . . . H8A H -0.1950 1.1080 0.7092 0.056 Uiso 1 1 d R . . H8B H -0.1361 1.0955 0.8568 0.056 Uiso 1 1 d R . . H8C H -0.1969 0.9890 0.7699 0.056 Uiso 1 1 d R . . C9 C 0.2701(5) 0.8887(6) 0.4599(5) 0.0197(13) Uani 1 1 d . . . H9A H 0.3027 0.8128 0.4556 0.024 Uiso 1 1 calc R . . H9B H 0.2470 0.9257 0.3789 0.024 Uiso 1 1 calc R . . C10 C 0.3775(6) 0.9561(6) 0.5623(6) 0.0308(13) Uani 1 1 d . . . H10A H 0.4060 0.9150 0.6418 0.037 Uiso 1 1 calc R . . H10B H 0.3418 1.0289 0.5724 0.037 Uiso 1 1 calc R . . C11 C 0.4952(7) 0.9781(7) 0.5358(8) 0.0460(18) Uani 1 1 d . . . H11A H 0.5542 1.0310 0.5982 0.055 Uiso 1 1 calc R . . H11B H 0.4665 1.0129 0.4528 0.055 Uiso 1 1 calc R . . C12 C 0.5678(6) 0.8675(15) 0.5400(9) 0.071(3) Uani 1 1 d . . . H12A H 0.6454 0.8631 0.6187 0.106 Uiso 1 1 d R . . H12B H 0.5921 0.8660 0.4708 0.106 Uiso 1 1 d R . . H12C H 0.5118 0.8036 0.5333 0.106 Uiso 1 1 d R . . C13 C -0.0421(6) 0.6322(4) 0.6921(5) 0.0198(11) Uani 1 1 d . . . C14 C -0.1604(6) 0.6512(5) 0.7025(6) 0.0237(12) Uani 1 1 d . . . H14 H -0.2396 0.6288 0.6369 0.028 Uiso 1 1 calc R . . C15 C -0.1605(6) 0.7022(6) 0.8080(6) 0.0236(14) Uani 1 1 d . . . H15 H -0.2381 0.7093 0.8172 0.028 Uiso 1 1 calc R . . C16 C -0.0398(5) 0.7442(5) 0.9033(5) 0.0213(11) Uani 1 1 d . . . C17 C -0.0397(6) 0.8081(5) 1.0052(6) 0.0261(12) Uani 1 1 d . . . H17 H -0.1180 0.8179 1.0125 0.031 Uiso 1 1 calc R . . C18 C 0.0735(6) 0.8562(6) 1.0942(5) 0.0284(14) Uani 1 1 d . . . H18 H 0.0722 0.8973 1.1617 0.034 Uiso 1 1 calc R . . C19 C 0.1903(6) 0.8427(5) 1.0820(6) 0.0274(14) Uani 1 1 d . . . H19 H 0.2668 0.8766 1.1411 0.033 Uiso 1 1 calc R . . C20 C 0.1944(5) 0.7800(5) 0.9837(6) 0.0231(12) Uani 1 1 d . . . H20 H 0.2735 0.7718 0.9776 0.028 Uiso 1 1 calc R . . C21 C 0.0785(5) 0.7278(4) 0.8915(5) 0.0182(10) Uani 1 1 d . . . C22 C 0.0793(5) 0.6628(5) 0.7861(5) 0.0198(11) Uani 1 1 d . . . C23 C 0.2038(5) 0.6352(4) 0.7784(5) 0.0193(11) Uani 1 1 d . . . C24 C 0.2233(5) 0.6622(4) 0.6708(5) 0.0184(10) Uani 1 1 d . . . C25 C 0.3449(6) 0.6456(5) 0.6689(6) 0.0241(12) Uani 1 1 d . . . H25 H 0.3556 0.6668 0.5973 0.029 Uiso 1 1 calc R . . C26 C 0.4489(6) 0.5990(5) 0.7701(6) 0.0300(13) Uani 1 1 d . . . H26 H 0.5303 0.5921 0.7684 0.036 Uiso 1 1 calc R . . C27 C 0.4320(6) 0.5612(5) 0.8769(5) 0.0235(12) Uani 1 1 d . . . C28 C 0.5344(6) 0.5029(5) 0.9790(6) 0.0276(13) Uani 1 1 d . . . H28 H 0.6167 0.4964 0.9792 0.033 Uiso 1 1 calc R . . C29 C 0.5144(6) 0.4568(6) 1.0756(5) 0.0312(14) Uani 1 1 d . . . H29 H 0.5817 0.4177 1.1405 0.037 Uiso 1 1 calc R . . C30 C 0.3914(6) 0.4688(5) 1.0764(5) 0.0281(13) Uani 1 1 d . . . H30 H 0.3778 0.4372 1.1427 0.034 Uiso 1 1 calc R . . C31 C 0.2902(6) 0.5259(5) 0.9819(5) 0.0224(11) Uani 1 1 d . . . H31 H 0.2095 0.5321 0.9851 0.027 Uiso 1 1 calc R . . C32 C 0.3075(5) 0.5756(5) 0.8793(5) 0.0191(10) 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 Sn1 0.01764(17) 0.01677(17) 0.01704(17) -0.00085(19) 0.00848(12) -0.00088(18) O1 0.0260(19) 0.0180(19) 0.0168(19) -0.0016(15) 0.0057(15) -0.0006(15) O2 0.0243(19) 0.0204(19) 0.0145(18) 0.0007(14) 0.0057(15) -0.0009(15) C1 0.031(3) 0.022(2) 0.014(2) -0.003(2) 0.008(2) -0.002(2) C2 0.033(3) 0.025(3) 0.029(3) 0.003(3) 0.008(3) -0.001(2) C3 0.031(3) 0.026(3) 0.030(3) -0.001(3) 0.002(3) -0.002(2) C4 0.027(3) 0.043(4) 0.049(4) 0.015(3) -0.002(3) -0.006(3) C5 0.033(3) 0.022(3) 0.009(2) -0.004(2) 0.006(2) -0.001(2) C6 0.030(3) 0.025(3) 0.018(3) 0.005(2) 0.011(2) 0.004(2) C7 0.036(3) 0.018(3) 0.032(3) -0.004(2) 0.022(3) 0.001(2) C8 0.051(5) 0.036(4) 0.039(4) -0.005(3) 0.033(4) -0.002(3) C9 0.036(2) 0.013(4) 0.027(2) -0.005(2) 0.030(2) -0.005(2) C10 0.022(3) 0.039(4) 0.027(3) -0.005(3) 0.006(2) -0.008(2) C11 0.023(3) 0.063(5) 0.048(4) 0.003(4) 0.011(3) -0.005(3) C12 0.028(3) 0.102(7) 0.100(6) 0.000(9) 0.044(4) 0.020(7) C13 0.029(3) 0.010(2) 0.022(3) 0.0012(19) 0.012(2) -0.002(2) C14 0.023(3) 0.018(3) 0.028(3) -0.004(2) 0.009(2) -0.001(2) C15 0.015(3) 0.033(3) 0.029(3) -0.004(3) 0.016(3) -0.002(2) C16 0.024(3) 0.019(3) 0.021(3) -0.002(2) 0.009(2) 0.002(2) C17 0.027(3) 0.027(3) 0.029(3) 0.000(3) 0.016(3) 0.001(2) C18 0.042(3) 0.022(4) 0.022(2) -0.007(2) 0.015(2) -0.002(3) C19 0.036(3) 0.022(3) 0.024(3) -0.003(2) 0.013(2) -0.003(2) C20 0.019(3) 0.022(3) 0.027(3) -0.001(2) 0.009(2) -0.002(2) C21 0.020(3) 0.016(2) 0.018(3) 0.004(2) 0.008(2) 0.0034(19) C22 0.021(3) 0.016(2) 0.021(3) 0.002(2) 0.007(2) 0.002(2) C23 0.022(3) 0.016(3) 0.020(3) -0.003(2) 0.009(2) -0.0009(19) C24 0.024(3) 0.012(2) 0.020(3) 0.003(2) 0.010(2) 0.005(2) C25 0.030(3) 0.021(3) 0.024(3) 0.004(2) 0.015(2) 0.002(2) C26 0.025(3) 0.031(3) 0.035(4) 0.008(3) 0.013(3) 0.008(2) C27 0.028(3) 0.021(3) 0.018(3) 0.001(2) 0.006(2) 0.003(2) C28 0.016(3) 0.034(3) 0.031(3) -0.003(3) 0.008(2) 0.007(2) C29 0.030(3) 0.040(4) 0.017(3) 0.005(3) 0.004(2) 0.010(3) C30 0.035(3) 0.033(3) 0.014(3) 0.005(2) 0.009(2) 0.009(3) C31 0.027(3) 0.025(3) 0.015(3) 0.000(2) 0.009(2) -0.001(2) C32 0.024(3) 0.018(2) 0.014(3) -0.003(2) 0.007(2) 0.001(2) _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 Sn1 C1 2.138(5) . y Sn1 O2 2.142(4) . y Sn1 C5 2.142(5) . y Sn1 C9 2.171(5) . y Sn1 O1 2.549(4) 2_556 y O1 C13 1.383(7) . y O1 Sn1 2.549(4) 2_546 y O2 C24 1.363(6) . y C1 C2 1.533(8) . ? C2 C3 1.515(8) . ? C3 C4 1.510(10) . ? C5 C6 1.514(8) . ? C6 C7 1.529(8) . ? C7 C8 1.498(9) . ? C9 C10 1.508(8) . ? C10 C11 1.510(9) . ? C11 C12 1.520(16) . ? C13 C22 1.384(8) . ? C13 C14 1.409(8) . ? C14 C15 1.372(8) . ? C15 C16 1.425(8) . ? C16 C17 1.407(8) . ? C16 C21 1.412(7) . ? C17 C18 1.373(8) . ? C18 C19 1.394(8) . ? C19 C20 1.382(8) . ? C20 C21 1.425(8) . ? C21 C22 1.452(8) . ? C22 C23 1.481(8) . ? C23 C24 1.403(7) . ? C23 C32 1.434(8) . ? C24 C25 1.394(8) . ? C25 C26 1.371(8) . ? C26 C27 1.414(8) . ? C27 C32 1.426(8) . ? C27 C28 1.427(8) . ? C28 C29 1.356(9) . ? C29 C30 1.398(9) . ? C30 C31 1.372(8) . ? C31 C32 1.421(7) . ? 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 C1 Sn1 O2 92.45(19) . . y C1 Sn1 C5 126.2(2) . . y O2 Sn1 C5 95.24(18) . . y C1 Sn1 C9 114.3(2) . . y O2 Sn1 C9 99.4(2) . . y C5 Sn1 C9 116.7(2) . . y C1 Sn1 O1 87.55(18) . 2_556 y O2 Sn1 O1 175.01(13) . 2_556 y C5 Sn1 O1 80.77(17) . 2_556 y C9 Sn1 O1 85.1(2) . 2_556 ? C13 O1 Sn1 131.3(3) . 2_546 ? C24 O2 Sn1 126.9(3) . . ? C2 C1 Sn1 118.5(4) . . ? C3 C2 C1 111.6(5) . . ? C4 C3 C2 114.4(6) . . ? C6 C5 Sn1 114.7(4) . . ? C5 C6 C7 112.2(5) . . ? C8 C7 C6 112.0(5) . . ? C10 C9 Sn1 112.3(4) . . ? C9 C10 C11 113.7(5) . . ? C10 C11 C12 111.0(7) . . ? O1 C13 C22 121.0(5) . . ? O1 C13 C14 116.3(5) . . ? C22 C13 C14 122.7(5) . . ? C15 C14 C13 121.0(5) . . ? C14 C15 C16 118.9(5) . . ? C17 C16 C21 120.0(5) . . ? C17 C16 C15 119.8(5) . . ? C21 C16 C15 120.1(5) . . ? C18 C17 C16 121.4(5) . . ? C17 C18 C19 119.2(5) . . ? C20 C19 C18 121.1(5) . . ? C19 C20 C21 120.6(5) . . ? C16 C21 C20 117.7(5) . . ? C16 C21 C22 120.4(5) . . ? C20 C21 C22 121.8(5) . . ? C13 C22 C21 116.3(5) . . ? C13 C22 C23 122.3(5) . . ? C21 C22 C23 121.3(5) . . ? C24 C23 C32 117.4(5) . . ? C24 C23 C22 121.6(5) . . ? C32 C23 C22 120.9(5) . . ? O2 C24 C25 118.9(5) . . ? O2 C24 C23 119.9(5) . . ? C25 C24 C23 121.2(5) . . ? C26 C25 C24 121.5(5) . . ? C25 C26 C27 119.8(5) . . ? C26 C27 C32 119.3(5) . . ? C26 C27 C28 121.3(5) . . ? C32 C27 C28 119.3(5) . . ? C29 C28 C27 121.4(5) . . ? C28 C29 C30 119.2(5) . . ? C31 C30 C29 121.8(5) . . ? C30 C31 C32 120.7(5) . . ? C31 C32 C27 117.5(5) . . ? C31 C32 C23 122.3(5) . . ? C27 C32 C23 120.1(5) . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 3.941 _refine_diff_density_min -0.750 _refine_diff_density_rms 0.150