Supplementary Material (ESI) for Green Chemistry This journal is © The Royal Society of Chemistry 2003 data_global _journal_coden_Cambridge 1048 _publ_contact_author_name 'Prof Robin D. Rogers' _publ_contact_author_address ; Department of Chemistry and Center for Green Manufacturing The University of Alabama Tuscaloosa AL 35487 UNITED STATES OF AMERICA ; _publ_contact_author_phone '+1 205 3484323' _publ_contact_author_fax '+1 205 3489104' _publ_contact_author_email rdrogers@bama.ua.edu _publ_requested_journal 'Green Chemistry' _publ_requested_coeditor_name ? _publ_contact_letter ; ? ; #============================================================================== # 3. TITLE AND AUTHOR LIST _publ_section_title ; Ionic liquids are not always green: hydrolysis of 1-butyl-3-methylimidazolium hexafluorophosphate ; loop_ _publ_author_name _publ_author_address 'Swatloski, Richard P.' ; Center for Green Manufacturing and Department of Chemistry University of Alabama Tuscaloosa AL 35487 USA ; 'Holbrey, John D.' ; Center for Green Manufacturing and Department of Chemistry University of Alabama Tuscaloosa AL 35487 USA ; 'Rogers, Robin D.' ; Center for Green Manufacturing and Department of Chemistry University of Alabama Tuscaloosa AL 35487 USA ; #============================================================================== data_Swatloski1 _database_code_CSD 210400 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ; '1-butyl-3-methylimidazolium fluoride monohydrate' ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H17 F N2 O' _chemical_formula_weight 176.24 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' N N 0.0061 0.0033 '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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.4317(17) _cell_length_b 10.439(2) _cell_length_c 11.313(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 995.7(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.176 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 384 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type sphere _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details SADABS _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 '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 4506 _diffrn_reflns_av_R_equivalents 0.0223 _diffrn_reflns_av_sigmaI/netI 0.0228 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.65 _diffrn_reflns_theta_max 23.22 _reflns_number_total 1429 _reflns_number_gt 1343 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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 ; 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 '0.0344, 0.1388' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.025(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00 _refine_ls_number_reflns 1429 _refine_ls_number_parameters 178 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0288 _refine_ls_R_factor_gt 0.0253 _refine_ls_wR_factor_ref 0.0631 _refine_ls_wR_factor_gt 0.0606 _refine_ls_goodness_of_fit_ref 1.007 _refine_ls_restrained_S_all 1.007 _refine_ls_shift/su_max 0.232 _refine_ls_shift/su_mean 0.027 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 F F -0.21125(10) -0.71580(9) -0.52205(8) 0.0379(3) Uani 1 1 d . . . O O -0.46950(19) -0.79651(15) -0.62806(13) 0.0538(4) Uani 1 1 d . . . H1OB H -0.550(3) -0.788(2) -0.577(2) 0.072(7) Uiso 1 1 d . . . H1OA H -0.383(3) -0.767(3) -0.582(2) 0.088(9) Uiso 1 1 d . . . N1 N -0.34040(15) -0.49414(13) -0.26735(11) 0.0305(3) Uani 1 1 d . . . N3 N -0.58626(15) -0.49801(13) -0.21589(11) 0.0290(3) Uani 1 1 d . . . C2 C -0.44528(19) -0.44767(16) -0.19054(15) 0.0300(4) Uani 1 1 d . . . H2A H -0.418(2) -0.3906(18) -0.1281(17) 0.038(5) Uiso 1 1 d . . . C4 C -0.5691(2) -0.58002(17) -0.31109(15) 0.0335(4) Uani 1 1 d . . . H4A H -0.657(2) -0.6253(17) -0.3414(15) 0.038(5) Uiso 1 1 d . . . C5 C -0.4160(2) -0.57744(16) -0.34310(15) 0.0338(4) Uani 1 1 d . . . H5A H -0.356(2) -0.6208(17) -0.4035(15) 0.034(5) Uiso 1 1 d . . . C6 C -0.7347(2) -0.47439(18) -0.14993(16) 0.0363(4) Uani 1 1 d . . . H6A H -0.815(2) -0.4540(17) -0.2079(16) 0.038(5) Uiso 1 1 d . . . H6B H -0.712(2) -0.401(2) -0.0954(18) 0.057(6) Uiso 1 1 d . . . C7 C -0.7848(2) -0.59165(18) -0.07973(16) 0.0385(5) Uani 1 1 d . . . H7A H -0.803(2) -0.6674(19) -0.1349(17) 0.049(5) Uiso 1 1 d . . . H7B H -0.887(2) -0.5689(18) -0.0402(15) 0.042(5) Uiso 1 1 d . . . C8 C -0.6658(2) -0.6307(2) 0.01412(16) 0.0397(5) Uani 1 1 d . . . H8A H -0.643(2) -0.553(2) 0.0676(16) 0.046(5) Uiso 1 1 d . . . H8B H -0.564(2) -0.6540(19) -0.0237(17) 0.048(5) Uiso 1 1 d . . . C9 C -0.7197(3) -0.7434(2) 0.08916(19) 0.0508(5) Uani 1 1 d . . . H9A H -0.641(3) -0.764(2) 0.156(2) 0.068(7) Uiso 1 1 d . . . H9B H -0.733(3) -0.823(3) 0.042(2) 0.082(8) Uiso 1 1 d . . . H9C H -0.828(2) -0.7245(19) 0.1267(17) 0.051(5) Uiso 1 1 d . . . C10 C -0.1709(2) -0.4608(2) -0.2696(2) 0.0443(5) Uani 1 1 d . . . H10A H -0.139(3) -0.419(3) -0.198(3) 0.098(10) Uiso 1 1 d . . . H10B H -0.153(3) -0.411(3) -0.342(3) 0.100(10) Uiso 1 1 d . . . H10C H -0.111(3) -0.537(2) -0.2810(19) 0.069(7) 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 F 0.0310(5) 0.0442(6) 0.0383(5) 0.0010(4) 0.0064(4) 0.0009(5) O 0.0482(8) 0.0678(10) 0.0453(8) -0.0108(7) 0.0062(7) -0.0164(8) N1 0.0301(7) 0.0256(7) 0.0359(8) -0.0017(7) 0.0016(6) 0.0005(6) N3 0.0290(7) 0.0294(7) 0.0286(7) -0.0049(6) -0.0015(6) 0.0012(7) C2 0.0336(9) 0.0274(9) 0.0291(8) -0.0027(7) -0.0031(8) 0.0018(8) C4 0.0369(10) 0.0332(10) 0.0303(9) -0.0044(8) -0.0066(8) -0.0001(8) C5 0.0426(11) 0.0292(9) 0.0297(9) -0.0037(7) 0.0014(9) 0.0034(9) C6 0.0299(9) 0.0426(11) 0.0364(9) -0.0019(8) -0.0005(8) 0.0074(8) C7 0.0319(10) 0.0456(11) 0.0378(10) -0.0077(9) 0.0032(8) -0.0011(9) C8 0.0328(10) 0.0465(11) 0.0397(10) 0.0015(9) 0.0004(9) -0.0007(9) C9 0.0574(14) 0.0491(12) 0.0459(11) 0.0059(10) 0.0017(11) -0.0063(11) C10 0.0309(10) 0.0382(11) 0.0636(14) 0.0018(10) 0.0066(9) -0.0026(9) _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 N1 C2 1.331(2) . ? N1 C5 1.377(2) . ? N1 C10 1.471(2) . ? N3 C2 1.331(2) . ? N3 C4 1.383(2) . ? N3 C6 1.478(2) . ? C4 C5 1.341(3) . ? C6 C7 1.519(3) . ? C7 C8 1.516(3) . ? C8 C9 1.520(3) . ? 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 N1 C5 109.20(14) . . ? C2 N1 C10 124.78(16) . . ? C5 N1 C10 126.01(15) . . ? C2 N3 C4 108.57(14) . . ? C2 N3 C6 125.56(13) . . ? C4 N3 C6 125.81(13) . . ? N3 C2 N1 107.98(14) . . ? C5 C4 N3 107.38(15) . . ? C4 C5 N1 106.86(15) . . ? N3 C6 C7 111.42(14) . . ? C6 C7 C8 113.47(16) . . ? C7 C8 C9 113.67(17) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 23.22 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.103 _refine_diff_density_min -0.106 _refine_diff_density_rms 0.027