# Supplementary Material (ESI) for Green Chemistry # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full 'Green Chemistry' _journal_coden_Cambridge 1048 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Puga, Alberto' _publ_contact_author_email K.SEDDON@QUB.AC.UK _publ_section_title ; New ionic liquids from azepane and 3-methylpiperidine exhibiting wide electrochemical windows ; loop_ _publ_author_name T.Belhocine S.A.Forsyth H.Q.N.Gunaratne M.Nieuwenhuyzen A.V.Puga K.R.Seddon G.Srinivasan K.Whiston # Attachment 'k05prr35.cif' data_k05prr35 _database_code_depnum_ccdc_archive 'CCDC 792935' #TrackingRef 'k05prr35.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H24 F3 N O2' _chemical_formula_weight 283.33 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' 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 Pbna loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x, -y+1/2, -z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x, y-1/2, z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.2840(2) _cell_length_b 13.2290(2) _cell_length_c 18.3910(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2988.63(8) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description colourless _exptl_crystal_colour plate _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.259 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1216 _exptl_absorpt_coefficient_mu 0.108 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.813 _exptl_absorpt_correction_T_max 1.257 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _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 KappaCCD _diffrn_measurement_method CCD _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 31969 _diffrn_reflns_av_R_equivalents 0.0964 _diffrn_reflns_av_sigmaI/netI 0.0326 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.17 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2619 _reflns_number_gt 2258 _reflns_threshold_expression >2sigma(I) _computing_data_collection KappaCCD _computing_data_reduction 'Denzo and Scalepak (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material 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 'calc w=1/[\s^2^(Fo^2^)+(0.1336P)^2^+4.4012P] 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 SHELXL _refine_ls_extinction_coef 0.017(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2619 _refine_ls_number_parameters 170 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0911 _refine_ls_R_factor_gt 0.0789 _refine_ls_wR_factor_ref 0.2428 _refine_ls_wR_factor_gt 0.2211 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _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 C1 C 1.0678(2) 0.0699(2) 0.29762(16) 0.0320(7) Uani 1 1 d . . . H1A H 1.1170 0.0163 0.2831 0.038 Uiso 1 1 calc R . . H1B H 1.1117 0.1288 0.3090 0.038 Uiso 1 1 calc R . . C2 C 1.0086(3) 0.0368(3) 0.36648(17) 0.0423(8) Uani 1 1 d . . . H2A H 1.0532 -0.0123 0.3919 0.051 Uiso 1 1 calc R . . H2B H 0.9411 0.0037 0.3529 0.051 Uiso 1 1 calc R . . C3 C 0.9829(3) 0.1240(3) 0.41802(18) 0.0514(10) Uani 1 1 d . . . H3A H 0.9585 0.0961 0.4640 0.062 Uiso 1 1 calc R . . H3B H 1.0494 0.1613 0.4272 0.062 Uiso 1 1 calc R . . C4 C 0.8968(3) 0.1974(3) 0.39052(19) 0.0520(10) Uani 1 1 d . . . H4A H 0.8944 0.2549 0.4232 0.062 Uiso 1 1 calc R . . H4B H 0.8265 0.1642 0.3929 0.062 Uiso 1 1 calc R . . C5 C 0.9139(3) 0.2364(3) 0.31312(18) 0.0407(8) Uani 1 1 d . . . H5A H 0.8647 0.2925 0.3045 0.049 Uiso 1 1 calc R . . H5B H 0.9877 0.2616 0.3085 0.049 Uiso 1 1 calc R . . C6 C 0.8945(2) 0.1555(2) 0.25530(16) 0.0326(7) Uani 1 1 d . . . H6A H 0.8401 0.1086 0.2734 0.039 Uiso 1 1 calc R . . H6B H 0.8647 0.1878 0.2124 0.039 Uiso 1 1 calc R . . C7 C 1.0625(2) 0.1559(2) 0.18084(16) 0.0344(7) Uani 1 1 d . . . H7A H 1.0194 0.1738 0.1393 0.052 Uiso 1 1 calc R . . H7B H 1.1238 0.1161 0.1655 0.052 Uiso 1 1 calc R . . H7C H 1.0879 0.2162 0.2043 0.052 Uiso 1 1 calc R . . C8 C 0.9599(2) -0.0029(2) 0.19742(16) 0.0305(7) Uani 1 1 d . . . H8A H 1.0249 -0.0400 0.1838 0.037 Uiso 1 1 calc R . . H8B H 0.9214 -0.0432 0.2332 0.037 Uiso 1 1 calc R . . C9 C 0.8880(3) 0.0076(2) 0.13060(17) 0.0375(8) Uani 1 1 d . . . H9A H 0.9259 0.0462 0.0936 0.045 Uiso 1 1 calc R . . H9B H 0.8220 0.0437 0.1433 0.045 Uiso 1 1 calc R . . C10 C 0.8593(3) -0.0964(2) 0.10104(19) 0.0433(8) Uani 1 1 d . . . H10A H 0.9258 -0.1349 0.0943 0.052 Uiso 1 1 calc R . . H10B H 0.8152 -0.1318 0.1366 0.052 Uiso 1 1 calc R . . C11 C 0.7990(4) -0.0926(3) 0.0307(2) 0.0586(11) Uani 1 1 d . . . H11A H 0.7832 -0.1601 0.0148 0.088 Uiso 1 1 calc R . . H11B H 0.8429 -0.0591 -0.0051 0.088 Uiso 1 1 calc R . . H11C H 0.7322 -0.0560 0.0372 0.088 Uiso 1 1 calc R . . N1 N 0.99455(18) 0.09570(17) 0.23311(12) 0.0272(6) Uani 1 1 d . . . C12 C 0.7636(2) -0.1288(2) 0.32948(17) 0.0313(7) Uani 1 1 d . A . C13 C 0.7384(3) -0.1636(2) 0.40717(18) 0.0379(8) Uani 1 1 d . . . F4 F 0.7393(3) -0.2678(2) 0.41169(17) 0.0489(9) Uiso 0.70 1 d P A 1 F5 F 0.8081(3) -0.1303(3) 0.45464(18) 0.0491(9) Uiso 0.70 1 d P A 1 F6 F 0.6410(3) -0.1349(3) 0.4309(2) 0.0636(12) Uiso 0.70 1 d P A 1 O1 O 0.73357(18) -0.04217(18) 0.31464(15) 0.0492(7) Uani 1 1 d . . . O2 O 0.8128(2) -0.19064(18) 0.29180(13) 0.0472(7) Uani 1 1 d . . . F7 F 0.6968(6) -0.2527(5) 0.4168(3) 0.0358(15) Uiso 0.30 1 d P A 2 F8 F 0.8384(6) -0.1569(6) 0.4471(4) 0.0405(17) Uiso 0.30 1 d P A 2 F9 F 0.6586(8) -0.1030(9) 0.4393(6) 0.068(3) Uiso 0.30 1 d P A 2 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 0.0255(13) 0.0349(15) 0.0356(16) 0.0025(12) -0.0049(11) -0.0003(11) C2 0.0349(15) 0.054(2) 0.0376(17) 0.0134(15) -0.0073(13) -0.0074(14) C3 0.0427(18) 0.082(3) 0.0298(16) -0.0017(16) 0.0006(14) -0.0122(18) C4 0.0403(17) 0.080(3) 0.0354(18) -0.0162(18) 0.0037(14) 0.0019(17) C5 0.0357(16) 0.0442(18) 0.0423(18) -0.0109(14) -0.0020(13) 0.0084(13) C6 0.0272(14) 0.0355(15) 0.0352(15) -0.0017(12) -0.0015(11) 0.0067(12) C7 0.0376(16) 0.0304(15) 0.0353(16) 0.0020(12) 0.0051(12) -0.0071(12) C8 0.0324(14) 0.0239(14) 0.0352(16) 0.0006(11) 0.0010(12) -0.0015(11) C9 0.0465(17) 0.0296(15) 0.0365(17) 0.0005(12) -0.0064(13) -0.0035(13) C10 0.0526(19) 0.0332(17) 0.0440(19) -0.0001(14) -0.0054(15) -0.0089(14) C11 0.075(3) 0.049(2) 0.052(2) -0.0040(17) -0.0157(19) -0.0102(19) N1 0.0253(11) 0.0262(12) 0.0302(13) 0.0010(9) 0.0001(9) 0.0000(9) C12 0.0213(13) 0.0317(15) 0.0408(17) 0.0024(12) -0.0061(11) -0.0035(11) C13 0.0375(16) 0.0362(17) 0.0400(17) -0.0010(13) -0.0035(13) -0.0044(13) O1 0.0384(13) 0.0376(13) 0.0715(17) 0.0186(12) 0.0008(11) 0.0076(10) O2 0.0512(14) 0.0438(13) 0.0465(14) -0.0062(11) 0.0080(11) 0.0042(11) _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 1.525(4) . ? C1 N1 1.527(3) . ? C2 C3 1.526(5) . ? C3 C4 1.522(6) . ? C4 C5 1.529(5) . ? C5 C6 1.527(4) . ? C6 N1 1.517(3) . ? C7 N1 1.502(4) . ? C8 C9 1.520(4) . ? C8 N1 1.521(3) . ? C9 C10 1.522(4) . ? C10 C11 1.491(5) . ? C12 O2 1.231(4) . ? C12 O1 1.235(4) . ? C12 C13 1.533(4) . ? C13 F7 1.296(7) . ? C13 F5 1.300(5) . ? C13 F6 1.329(5) . ? C13 F4 1.381(4) . ? C13 F9 1.397(11) . ? C13 F8 1.435(8) . ? 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 N1 115.4(2) . . ? C1 C2 C3 113.4(3) . . ? C4 C3 C2 114.8(3) . . ? C3 C4 C5 115.5(3) . . ? C6 C5 C4 113.0(3) . . ? N1 C6 C5 115.2(2) . . ? C9 C8 N1 115.7(2) . . ? C8 C9 C10 109.9(3) . . ? C11 C10 C9 113.2(3) . . ? C7 N1 C6 110.2(2) . . ? C7 N1 C8 109.5(2) . . ? C6 N1 C8 109.7(2) . . ? C7 N1 C1 106.7(2) . . ? C6 N1 C1 112.6(2) . . ? C8 N1 C1 108.0(2) . . ? O2 C12 O1 129.7(3) . . ? O2 C12 C13 115.1(3) . . ? O1 C12 C13 115.1(3) . . ? F7 C13 F5 118.4(4) . . ? F7 C13 F6 82.0(4) . . ? F5 C13 F6 106.0(3) . . ? F7 C13 F4 24.2(3) . . ? F5 C13 F4 107.0(3) . . ? F6 C13 F4 105.8(3) . . ? F7 C13 F9 100.8(6) . . ? F5 C13 F9 89.1(5) . . ? F6 C13 F9 20.9(4) . . ? F4 C13 F9 123.6(5) . . ? F7 C13 F8 108.9(5) . . ? F5 C13 F8 21.7(3) . . ? F6 C13 F8 125.8(4) . . ? F4 C13 F8 91.4(4) . . ? F9 C13 F8 110.4(6) . . ? F7 C13 C12 118.7(4) . . ? F5 C13 C12 113.0(3) . . ? F6 C13 C12 113.7(3) . . ? F4 C13 C12 110.7(3) . . ? F9 C13 C12 111.3(5) . . ? F8 C13 C12 106.6(3) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.699 _refine_diff_density_min -0.742 _refine_diff_density_rms 0.092