# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2003 data_global _journal_coden_Cambridge 440 loop_ _publ_author_name 'Jennifer Pringle' 'Krisztian Baranyai' 'Glen B. Deacon' 'Craig M. Forsyth' 'Jake Golding' 'Douglas MacFarlane' 'Janet L. Scott' _publ_contact_author_name 'Dr Jennifer Pringle' _publ_contact_author_address ; School of Chemistry Monash University Wellington Road Clayton Melbourne Victoria 3800 AUSTRALIA ; _publ_contact_author_email J.PRINGLE@SCI.MONASH.EDU.AU _publ_requested_journal 'New Journal of Chemistry' _publ_section_title ; The effect of anion fluorination in ionic liquids - physical properties of a range of bis(methanesulfonyl)amide salts. ; data_p11bmsa _database_code_CSD 210766 _audit_creation_method SHELXL-97 _chemical_name_systematic ; N,N-dimethylpyrrolidinium dbis(methylsunphonyl)amide ; _chemical_name_common p11(NMes2) _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H20 N2 O4 S2' _chemical_formula_weight 272.38 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.2308(1) _cell_length_b 10.5652(1) _cell_length_c 14.6405(2) _cell_angle_alpha 90.00 _cell_angle_beta 95.159(1) _cell_angle_gamma 90.00 _cell_volume 1268.0(4) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 18383 _cell_measurement_theta_min 2.79 _cell_measurement_theta_max 28.29 _exptl_crystal_description prismatic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.075 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.427 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 0.422 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details 'performed as part of the DENZO-SMN package' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 Kappa CCD' _diffrn_measurement_method 'psi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number none _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18383 _diffrn_reflns_av_R_equivalents 0.0429 _diffrn_reflns_av_sigmaI/netI 0.0380 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.79 _diffrn_reflns_theta_max 28.29 _reflns_number_total 3104 _reflns_number_gt 2477 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius Collect' _computing_cell_refinement DENZO-SMN _computing_data_reduction 'X -Seed' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed / POV-Ray' _computing_publication_material 'Microsoft Office 2000' _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^)+(0.0454P)^2^+0.0968P] 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_number_reflns 3104 _refine_ls_number_parameters 225 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0466 _refine_ls_R_factor_gt 0.0308 _refine_ls_wR_factor_ref 0.0819 _refine_ls_wR_factor_gt 0.0776 _refine_ls_goodness_of_fit_ref 1.085 _refine_ls_restrained_S_all 1.085 _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 S1 S 0.23997(4) 0.34690(3) 0.27776(2) 0.01404(11) Uani 1 1 d . . . O1 O 0.32322(14) 0.40449(10) 0.20587(7) 0.0231(3) Uani 1 1 d . . . N1 N -0.26137(14) 0.09124(11) 0.39819(8) 0.0132(3) Uani 1 1 d . . . C1 C -0.14724(19) 0.00618(14) 0.35148(10) 0.0162(3) Uani 1 1 d . . . H1A H -0.1607(18) -0.0794(15) 0.3721(10) 0.012(4) Uiso 1 1 d . . . H1B H -0.0353(19) 0.0360(14) 0.3704(10) 0.011(4) Uiso 1 1 d . . . H7C H 0.146(2) 0.1473(17) 0.2894(13) 0.035(5) Uiso 1 1 d . . . S2 S 0.30679(5) 0.32010(3) 0.46548(2) 0.01701(11) Uani 1 1 d . . . O2 O 0.08652(13) 0.40460(10) 0.29669(7) 0.0225(3) Uani 1 1 d . . . N2 N 0.36789(14) 0.33984(11) 0.36645(8) 0.0159(3) Uani 1 1 d . . . C2 C -0.1931(2) 0.02892(14) 0.24975(10) 0.0176(3) Uani 1 1 d . . . H2A H -0.2779(19) -0.0283(14) 0.2259(10) 0.012(4) Uiso 1 1 d . . . H2B H -0.100(2) 0.0169(15) 0.2157(11) 0.019(4) Uiso 1 1 d . . . O3 O 0.45072(14) 0.29347(11) 0.52698(7) 0.0270(3) Uani 1 1 d . . . C3 C -0.2562(2) 0.16682(15) 0.24394(11) 0.0189(3) Uani 1 1 d . . . H3A H -0.364(2) 0.1677(14) 0.2127(11) 0.017(4) Uiso 1 1 d . . . H3B H -0.193(2) 0.2187(17) 0.2119(12) 0.026(5) Uiso 1 1 d . . . O4 O 0.17643(14) 0.22793(11) 0.46752(7) 0.0271(3) Uani 1 1 d . . . C4 C -0.25650(19) 0.21148(14) 0.34260(11) 0.0163(3) Uani 1 1 d . . . H4A H -0.347(2) 0.2637(15) 0.3539(10) 0.016(4) Uiso 1 1 d . . . H4B H -0.156(2) 0.2505(15) 0.3617(11) 0.018(4) Uiso 1 1 d . . . C5 C -0.42964(18) 0.03572(15) 0.39028(11) 0.0167(3) Uani 1 1 d . . . H5A H -0.468(2) 0.0242(15) 0.3285(12) 0.021(4) Uiso 1 1 d . . . H5B H -0.427(2) -0.0452(16) 0.4217(11) 0.023(4) Uiso 1 1 d . . . H5C H -0.500(2) 0.0923(16) 0.4205(11) 0.019(4) Uiso 1 1 d . . . C6 C -0.2072(2) 0.11216(17) 0.49715(11) 0.0210(3) Uani 1 1 d . . . H6A H -0.105(2) 0.1446(16) 0.5001(12) 0.025(5) Uiso 1 1 d . . . H6B H -0.281(2) 0.1700(17) 0.5193(12) 0.025(5) Uiso 1 1 d . . . H6C H -0.215(2) 0.0282(17) 0.5274(11) 0.024(4) Uiso 1 1 d . . . C7 C 0.1975(2) 0.19031(15) 0.24246(12) 0.0224(4) Uani 1 1 d . . . H7A H 0.123(2) 0.1953(16) 0.1909(13) 0.026(5) Uiso 1 1 d . . . H7B H 0.297(2) 0.1536(17) 0.2303(12) 0.032(5) Uiso 1 1 d . . . C8 C 0.2301(2) 0.46784(16) 0.49862(12) 0.0239(4) Uani 1 1 d . . . H8A H 0.140(2) 0.4905(16) 0.4552(12) 0.029(5) Uiso 1 1 d . . . H8B H 0.318(2) 0.5258(18) 0.4995(12) 0.033(5) Uiso 1 1 d . . . H8C H 0.193(2) 0.4565(16) 0.5552(12) 0.022(4) 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 S1 0.0140(2) 0.01418(18) 0.01389(19) 0.00219(14) 0.00101(14) -0.00040(13) O1 0.0319(7) 0.0218(6) 0.0165(5) 0.0023(5) 0.0069(5) -0.0086(5) N1 0.0118(6) 0.0158(6) 0.0121(6) 0.0006(5) 0.0014(5) -0.0001(5) C1 0.0156(8) 0.0170(7) 0.0165(7) 0.0000(6) 0.0031(6) 0.0032(6) S2 0.0169(2) 0.0192(2) 0.01458(19) 0.00243(15) -0.00032(15) 0.00172(14) O2 0.0171(6) 0.0292(6) 0.0206(6) 0.0023(5) -0.0013(4) 0.0090(5) N2 0.0107(6) 0.0212(6) 0.0157(6) 0.0004(5) 0.0004(5) 0.0013(5) C2 0.0165(8) 0.0201(8) 0.0163(7) -0.0009(6) 0.0027(6) 0.0013(6) O3 0.0261(6) 0.0333(6) 0.0200(6) 0.0005(5) -0.0074(5) 0.0091(5) C3 0.0191(8) 0.0223(8) 0.0156(7) 0.0049(6) 0.0031(6) 0.0015(6) O4 0.0304(7) 0.0286(6) 0.0225(6) 0.0066(5) 0.0040(5) -0.0099(5) C4 0.0143(8) 0.0139(7) 0.0210(8) 0.0025(6) 0.0022(6) -0.0001(6) C5 0.0141(8) 0.0197(8) 0.0164(8) 0.0004(6) 0.0019(6) -0.0035(6) C6 0.0177(9) 0.0313(9) 0.0136(7) -0.0031(7) -0.0017(6) -0.0010(7) C7 0.0236(9) 0.0174(8) 0.0253(9) 0.0005(7) -0.0026(8) -0.0046(7) C8 0.0257(10) 0.0276(9) 0.0188(8) -0.0020(7) 0.0046(7) 0.0067(7) _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 S1 O1 1.4411(11) . ? S1 O2 1.4514(11) . ? S1 N2 1.5983(13) . ? S1 C7 1.7590(16) . ? N1 C6 1.4934(19) . ? N1 C5 1.4989(18) . ? N1 C1 1.5078(18) . ? N1 C4 1.5112(19) . ? C1 C2 1.522(2) . ? S2 O3 1.4496(12) . ? S2 O4 1.4513(12) . ? S2 N2 1.5904(13) . ? S2 C8 1.7678(17) . ? N2 N1 4.0213(18) 1_655 ? C2 C3 1.547(2) . ? C3 C4 1.520(2) . ? 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 O1 S1 O2 116.18(7) . . ? O1 S1 N2 106.94(7) . . ? O2 S1 N2 112.67(6) . . ? O1 S1 C7 106.12(8) . . ? O2 S1 C7 107.32(8) . . ? N2 S1 C7 107.09(7) . . ? C6 N1 C5 109.02(12) . . ? C6 N1 C1 112.62(12) . . ? C5 N1 C1 109.92(11) . . ? C6 N1 C4 112.21(12) . . ? C5 N1 C4 110.88(11) . . ? C1 N1 C4 102.06(11) . . ? N1 C1 C2 103.89(11) . . ? O3 S2 O4 114.92(7) . . ? O3 S2 N2 106.49(7) . . ? O4 S2 N2 113.68(7) . . ? O3 S2 C8 107.03(8) . . ? O4 S2 C8 107.70(8) . . ? N2 S2 C8 106.52(8) . . ? S2 N2 S1 120.50(8) . . ? S2 N2 N1 96.20(6) . 1_655 ? S1 N2 N1 124.19(6) . 1_655 ? C1 C2 C3 104.77(12) . . ? C4 C3 C2 105.63(12) . . ? N1 C4 C3 104.67(12) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C7 H7C O1 0.96(2) 2.578(18) 3.121(2) 116.3(13) 2_545 C7 H7A O3 0.929(18) 2.679(19) 3.599(2) 170.9(15) 4_565 C5 H5A O2 0.937(17) 2.365(18) 3.232(2) 153.6(13) 2_445 C1 H1B O1 0.989(15) 2.565(15) 3.0618(19) 111.0(10) 2_545 C6 H6B O3 0.942(19) 2.572(19) 3.465(2) 158.2(14) 1_455 C2 H2A O2 0.965(15) 2.630(15) 3.504(2) 150.9(12) 2_445 C6 H6C O1 0.996(18) 2.698(16) 3.049(2) 100.9(11) 4_566 C5 H5C O3 0.965(17) 2.689(17) 3.570(2) 152.0(13) 1_455 C4 H4A N2 0.953(16) 2.504(17) 3.422(2) 162.0(13) 1_455 _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.282 _refine_diff_density_min -0.441 _refine_diff_density_rms 0.073