# Supplementary Material (ESI) for Green Chemistry # This journal is © The Royal Society of Chemistry 2003 data_global _publ_contact_author_email rdrogers@bama.ua.edu _publ_contact_author_name 'Prof Robin D. Rogers' _journal_name_full 'Green Chemistry' _journal_coden_Cambridge 1048 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name J.D.Holbrey A.E.Visser S.K.Spear W.M.Reichert R.P.Swatloski ; G.A.Broker ; R.D.Rogers data_jdh2 _database_code_CSD 202389 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point 360K _chemical_formula_moiety ? _chemical_formula_sum 'C14 H24 F12 N4 O2 P2' _chemical_formula_weight 570.31 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' P P 0.1023 0.0942 '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 11.761(4) _cell_length_b 16.685(6) _cell_length_c 11.864(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.504(7) _cell_angle_gamma 90.00 _cell_volume 2328.0(15) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 843 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.627 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1160 _exptl_absorpt_coefficient_mu 0.302 _exptl_absorpt_correction_type SADABS _exptl_absorpt_correction_T_min 0.71 _exptl_absorpt_correction_T_max 0.97 _exptl_absorpt_process_details ? _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 '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 5523 _diffrn_reflns_av_R_equivalents 0.0220 _diffrn_reflns_av_sigmaI/netI 0.0501 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 1.73 _diffrn_reflns_theta_max 23.29 _reflns_number_total 3168 _reflns_number_gt 2210 _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 fullcycle _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0693P)^2^+0.1196P] 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 0.0035(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3168 _refine_ls_number_parameters 442 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0695 _refine_ls_R_factor_gt 0.0458 _refine_ls_wR_factor_ref 0.1219 _refine_ls_wR_factor_gt 0.1165 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _refine_ls_shift/su_max 0.064 _refine_ls_shift/su_mean 0.003 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 P1 P 0.20545(9) 0.18853(6) 0.93334(7) 0.0370(3) Uani 1 1 d . . . P2 P 0.69104(9) 0.24098(6) 0.92872(7) 0.0369(3) Uani 1 1 d . . . F1 F 0.3381(2) 0.20444(16) 0.9187(2) 0.0715(8) Uani 1 1 d . . . F2 F 0.1772(3) 0.27138(13) 0.8766(2) 0.0739(9) Uani 1 1 d . . . F3 F 0.2357(2) 0.10451(12) 0.99046(19) 0.0618(7) Uani 1 1 d . . . F4 F 0.2092(2) 0.22998(12) 1.05455(16) 0.0487(6) Uani 1 1 d . . . F5 F 0.2015(2) 0.14643(14) 0.81215(17) 0.0649(8) Uani 1 1 d . . . F6 F 0.0746(2) 0.16916(14) 0.94772(17) 0.0587(7) Uani 1 1 d . . . F7A F 0.7499(6) 0.1573(3) 0.9407(5) 0.142(3) Uani 0.60 1 d P A 1 F8A F 0.8084(4) 0.2828(3) 0.9340(4) 0.0971(17) Uani 0.60 1 d P A 1 F9A F 0.5694(4) 0.1999(3) 0.9242(4) 0.0894(15) Uani 0.60 1 d P A 1 F10A F 0.6835(4) 0.2451(3) 1.0585(3) 0.0870(16) Uani 0.60 1 d P A 1 F11A F 0.6316(5) 0.3236(2) 0.9151(4) 0.0924(17) Uani 0.60 1 d P A 1 F12A F 0.6950(4) 0.2319(3) 0.7974(3) 0.0735(14) Uani 0.60 1 d P A 1 F7B F 0.8173(5) 0.2091(4) 0.9252(5) 0.0686(18) Uani 0.40 1 d P A 2 F8B F 0.7248(8) 0.3131(4) 0.8501(6) 0.104(3) Uani 0.40 1 d P A 2 F9B F 0.6643(8) 0.1713(5) 1.0078(7) 0.118(3) Uani 0.40 1 d P A 2 F10B F 0.7276(7) 0.2935(4) 1.0370(6) 0.094(3) Uani 0.40 1 d P A 2 F11B F 0.5705(6) 0.2775(5) 0.9375(5) 0.087(2) Uani 0.40 1 d P A 2 F12B F 0.6584(9) 0.1932(5) 0.8250(7) 0.142(4) Uani 0.40 1 d P A 2 O9 O 0.1880(2) 0.49517(13) 0.87575(19) 0.0419(7) Uani 1 1 d . . . O12 O 0.3517(2) 0.44418(13) 1.04763(18) 0.0354(6) Uani 1 1 d . . . N1 N -0.0276(3) 0.34567(18) 0.6863(2) 0.0375(8) Uani 1 1 d . . . N3 N 0.0476(3) 0.46322(17) 0.6809(2) 0.0393(8) Uani 1 1 d . . . N15 N 0.5155(3) 0.47492(16) 1.2201(2) 0.0334(8) Uani 1 1 d . . . N17 N 0.5256(3) 0.59449(17) 1.2870(2) 0.0339(8) Uani 1 1 d . . . C2 C 0.0668(4) 0.3869(2) 0.7007(3) 0.0353(9) Uani 1 1 d . . . H2A H 0.141(3) 0.368(2) 0.717(3) 0.038(11) Uiso 1 1 d . . . C4 C -0.0649(5) 0.4714(3) 0.6533(4) 0.0609(14) Uani 1 1 d . . . H4A H -0.106(4) 0.516(3) 0.638(3) 0.066(14) Uiso 1 1 d . . . C5 C -0.1112(5) 0.3986(3) 0.6565(4) 0.0608(14) Uani 1 1 d . . . H5A H -0.178(4) 0.382(2) 0.643(3) 0.045(13) Uiso 1 1 d . . . C6 C -0.0400(4) 0.2584(2) 0.6921(3) 0.0487(11) Uani 1 1 d . . . H6A H 0.0349 0.2332 0.6865 0.12(2) Uiso 1 1 calc R . . H6B H -0.0886 0.2400 0.6297 0.11(2) Uiso 1 1 calc R . . H6C H -0.0748 0.2436 0.7640 0.111(19) Uiso 1 1 calc R . . C7 C 0.1305(5) 0.5282(3) 0.6899(3) 0.0501(12) Uani 1 1 d . . . H7A H 0.103(4) 0.566(3) 0.646(3) 0.063(14) Uiso 1 1 d . . . H7B H 0.205(3) 0.508(2) 0.666(3) 0.032(11) Uiso 1 1 d . . . C8 C 0.1422(5) 0.5582(2) 0.8090(3) 0.0451(11) Uani 1 1 d . . . H8A H 0.186(3) 0.602(2) 0.818(3) 0.032(10) Uiso 1 1 d . . . H8B H 0.065(3) 0.5747(18) 0.839(2) 0.023(9) Uiso 1 1 d . . . C10 C 0.1810(4) 0.5115(3) 0.9937(3) 0.0420(10) Uani 1 1 d . . . H10A H 0.098(4) 0.518(2) 1.016(3) 0.046(11) Uiso 1 1 d . . . H10B H 0.223(3) 0.555(2) 1.005(3) 0.032(10) Uiso 1 1 d . . . C11 C 0.2310(4) 0.4418(3) 1.0568(3) 0.0410(10) Uani 1 1 d . . . H11A H 0.211(3) 0.4466(18) 1.135(3) 0.028(9) Uiso 1 1 d . . . H11B H 0.205(3) 0.386(2) 1.029(3) 0.055(12) Uiso 1 1 d . . . C13 C 0.4077(4) 0.3799(2) 1.1042(3) 0.0383(10) Uani 1 1 d . . . H13A H 0.413(3) 0.335(2) 1.055(3) 0.030(9) Uiso 1 1 d . . . H13B H 0.363(3) 0.3612(18) 1.159(3) 0.026(9) Uiso 1 1 d . . . C14 C 0.5237(4) 0.4072(2) 1.1400(4) 0.0421(11) Uani 1 1 d . . . H14A H 0.562(3) 0.366(2) 1.176(3) 0.049(12) Uiso 1 1 d . . . H14B H 0.559(3) 0.4249(18) 1.082(3) 0.021(9) Uiso 1 1 d . . . C16 C 0.5507(3) 0.5488(2) 1.2008(3) 0.0339(9) Uani 1 1 d . . . H16A H 0.586(3) 0.563(2) 1.137(3) 0.051(12) Uiso 1 1 d . . . C18 C 0.4706(4) 0.5477(3) 1.3654(3) 0.0498(12) Uani 1 1 d . . . H18A H 0.444(3) 0.570(2) 1.430(3) 0.038(10) Uiso 1 1 d . . . C19 C 0.4645(4) 0.4731(3) 1.3239(3) 0.0505(12) Uani 1 1 d . . . H19A H 0.431(4) 0.425(3) 1.350(3) 0.073(14) Uiso 1 1 d . . . C20 C 0.5518(4) 0.6804(2) 1.2985(3) 0.0451(11) Uani 1 1 d . . . H20A H 0.4825 0.7096 1.3182 0.093(17) Uiso 1 1 calc R . . H20B H 0.5811 0.7008 1.2269 0.056(12) Uiso 1 1 calc R . . H20C H 0.6092 0.6880 1.3579 0.059(12) Uiso 1 1 calc R . . 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 P1 0.0451(7) 0.0328(6) 0.0329(5) -0.0010(5) 0.0022(4) -0.0053(5) P2 0.0372(7) 0.0413(6) 0.0321(5) -0.0051(5) 0.0010(4) 0.0051(5) F1 0.0544(19) 0.090(2) 0.0707(16) -0.0057(14) 0.0148(13) -0.0214(15) F2 0.120(3) 0.0408(15) 0.0604(16) 0.0119(12) -0.0188(15) 0.0045(14) F3 0.079(2) 0.0341(13) 0.0721(15) 0.0039(12) -0.0013(13) 0.0048(12) F4 0.0638(18) 0.0439(13) 0.0384(12) -0.0089(10) -0.0057(10) -0.0033(12) F5 0.084(2) 0.0700(17) 0.0407(13) -0.0185(12) 0.0133(12) -0.0147(14) F6 0.0423(17) 0.0798(18) 0.0540(14) -0.0124(12) 0.0003(11) -0.0107(13) F7A 0.194(7) 0.112(4) 0.120(4) -0.022(4) -0.033(4) 0.116(5) F8A 0.067(4) 0.139(5) 0.086(3) -0.018(3) -0.012(3) -0.041(3) F9A 0.074(4) 0.096(4) 0.099(3) 0.002(3) 0.005(3) -0.043(3) F10A 0.080(4) 0.152(5) 0.029(2) -0.004(2) 0.003(2) 0.029(3) F11A 0.139(5) 0.044(3) 0.093(3) -0.025(2) -0.036(3) 0.031(3) F12A 0.054(3) 0.140(4) 0.0263(19) -0.016(2) 0.0014(17) 0.017(3) F7B 0.039(4) 0.103(5) 0.065(4) 0.005(4) 0.014(3) 0.033(3) F8B 0.163(9) 0.060(4) 0.089(5) 0.034(4) 0.042(5) 0.024(5) F9B 0.129(8) 0.087(6) 0.139(7) 0.054(5) -0.002(6) -0.036(5) F10B 0.115(7) 0.081(5) 0.085(5) -0.054(4) -0.042(4) 0.022(4) F11B 0.041(5) 0.141(7) 0.080(4) -0.020(4) -0.007(3) 0.037(4) F12B 0.193(11) 0.110(7) 0.122(7) -0.086(6) -0.078(7) 0.009(6) O9 0.057(2) 0.0276(14) 0.0408(15) -0.0013(12) -0.0063(12) 0.0039(13) O12 0.0390(19) 0.0295(14) 0.0376(13) 0.0053(11) 0.0010(11) -0.0029(12) N1 0.038(2) 0.0385(19) 0.0358(17) -0.0035(15) -0.0037(14) 0.0034(17) N3 0.055(3) 0.0292(19) 0.0334(16) 0.0007(14) -0.0052(15) 0.0047(17) N15 0.049(2) 0.0247(18) 0.0266(16) -0.0002(13) -0.0025(14) 0.0012(15) N17 0.041(2) 0.0304(17) 0.0303(16) 0.0006(14) -0.0037(14) 0.0001(15) C2 0.037(3) 0.036(2) 0.033(2) 0.0030(17) -0.0034(19) 0.002(2) C4 0.066(4) 0.040(3) 0.076(3) -0.006(3) -0.032(3) 0.018(3) C5 0.039(4) 0.065(4) 0.078(3) -0.016(3) -0.022(3) 0.013(3) C6 0.058(3) 0.036(2) 0.053(3) -0.005(2) 0.003(2) -0.012(2) C7 0.071(4) 0.034(3) 0.045(3) 0.014(2) -0.004(2) -0.002(2) C8 0.055(4) 0.025(2) 0.055(3) 0.003(2) -0.004(2) -0.002(2) C10 0.043(3) 0.037(3) 0.046(2) -0.005(2) 0.001(2) 0.000(2) C11 0.040(3) 0.045(3) 0.038(2) 0.006(2) 0.0039(19) -0.007(2) C13 0.051(3) 0.030(2) 0.034(2) -0.001(2) 0.003(2) -0.001(2) C14 0.054(3) 0.031(2) 0.041(2) -0.003(2) 0.002(2) 0.008(2) C16 0.033(3) 0.038(2) 0.031(2) 0.0006(18) 0.0040(17) -0.0004(18) C18 0.073(4) 0.046(3) 0.030(2) -0.002(2) 0.009(2) -0.005(2) C19 0.073(4) 0.039(3) 0.039(2) 0.006(2) 0.006(2) -0.012(2) C20 0.059(3) 0.029(2) 0.047(2) -0.0020(19) -0.010(2) -0.003(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 P1 F2 1.572(2) . ? P1 F6 1.583(3) . ? P1 F1 1.593(3) . ? P1 F3 1.596(2) . ? P1 F4 1.596(2) . ? P1 F5 1.600(2) . ? P2 F12B 1.513(6) . ? P2 F9B 1.528(7) . ? P2 F10A 1.545(4) . ? P2 F8A 1.547(5) . ? P2 F11B 1.547(6) . ? P2 F11A 1.553(4) . ? P2 F7A 1.564(5) . ? P2 F12A 1.566(3) . ? P2 F8B 1.576(6) . ? P2 F7B 1.578(6) . ? P2 F9A 1.587(5) . ? P2 F10B 1.611(6) . ? O9 C8 1.420(4) . ? O9 C10 1.429(4) . ? O12 C13 1.424(4) . ? O12 C11 1.425(5) . ? N1 C2 1.316(5) . ? N1 C5 1.365(5) . ? N1 C6 1.465(4) . ? N3 C2 1.314(4) . ? N3 C4 1.367(6) . ? N3 C7 1.462(5) . ? N15 C16 1.321(4) . ? N15 C19 1.374(5) . ? N15 C14 1.481(4) . ? N17 C16 1.311(4) . ? N17 C18 1.380(5) . ? N17 C20 1.472(4) . ? C4 C5 1.332(7) . ? C7 C8 1.504(6) . ? C10 C11 1.500(5) . ? C13 C14 1.496(6) . ? C18 C19 1.340(6) . ? 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 F2 P1 F6 91.37(15) . . ? F2 P1 F1 90.57(16) . . ? F6 P1 F1 177.82(15) . . ? F2 P1 F3 179.28(16) . . ? F6 P1 F3 89.33(14) . . ? F1 P1 F3 88.72(14) . . ? F2 P1 F4 90.51(12) . . ? F6 P1 F4 90.59(12) . . ? F1 P1 F4 90.38(13) . . ? F3 P1 F4 89.65(12) . . ? F2 P1 F5 89.80(13) . . ? F6 P1 F5 89.22(13) . . ? F1 P1 F5 89.80(13) . . ? F3 P1 F5 90.04(13) . . ? F4 P1 F5 179.64(14) . . ? F12B P2 F9B 92.7(5) . . ? F12B P2 F10A 144.9(5) . . ? F9B P2 F10A 53.7(3) . . ? F12B P2 F8A 119.4(5) . . ? F9B P2 F8A 120.4(3) . . ? F10A P2 F8A 89.9(3) . . ? F12B P2 F11B 92.1(5) . . ? F9B P2 F11B 93.7(5) . . ? F10A P2 F11B 81.6(2) . . ? F8A P2 F11B 129.6(3) . . ? F12B P2 F11A 105.8(4) . . ? F9B P2 F11A 130.1(4) . . ? F10A P2 F11A 92.0(3) . . ? F8A P2 F11A 90.3(3) . . ? F11B P2 F11A 41.1(3) . . ? F12B P2 F7A 73.3(4) . . ? F9B P2 F7A 50.1(4) . . ? F10A P2 F7A 88.8(3) . . ? F8A P2 F7A 90.3(4) . . ? F11B P2 F7A 138.6(3) . . ? F11A P2 F7A 179.1(3) . . ? F12B P2 F12A 31.7(5) . . ? F9B P2 F12A 123.0(4) . . ? F10A P2 F12A 176.6(3) . . ? F8A P2 F12A 92.8(2) . . ? F11B P2 F12A 98.1(2) . . ? F11A P2 F12A 90.0(2) . . ? F7A P2 F12A 89.2(3) . . ? F12B P2 F8B 89.1(5) . . ? F9B P2 F8B 177.1(5) . . ? F10A P2 F8B 124.9(3) . . ? F8A P2 F8B 56.6(4) . . ? F11B P2 F8B 88.6(4) . . ? F11A P2 F8B 51.4(3) . . ? F7A P2 F8B 128.5(3) . . ? F12A P2 F8B 58.4(3) . . ? F12B P2 F7B 91.9(5) . . ? F9B P2 F7B 87.6(4) . . ? F10A P2 F7B 96.0(2) . . ? F8A P2 F7B 46.7(3) . . ? F11B P2 F7B 175.8(4) . . ? F11A P2 F7B 136.0(3) . . ? F7A P2 F7B 44.4(3) . . ? F12A P2 F7B 84.5(2) . . ? F8B P2 F7B 90.0(4) . . ? F12B P2 F9A 61.5(5) . . ? F9B P2 F9A 60.1(3) . . ? F10A P2 F9A 89.6(3) . . ? F8A P2 F9A 178.7(3) . . ? F11B P2 F9A 49.2(3) . . ? F11A P2 F9A 88.6(3) . . ? F7A P2 F9A 90.9(4) . . ? F12A P2 F9A 87.7(2) . . ? F8B P2 F9A 122.8(4) . . ? F7B P2 F9A 134.6(3) . . ? F12B P2 F10B 178.4(6) . . ? F9B P2 F10B 88.8(5) . . ? F10A P2 F10B 36.7(3) . . ? F8A P2 F10B 59.4(3) . . ? F11B P2 F10B 88.3(4) . . ? F11A P2 F10B 73.5(2) . . ? F7A P2 F10B 107.4(3) . . ? F12A P2 F10B 146.7(3) . . ? F8B P2 F10B 89.4(4) . . ? F7B P2 F10B 87.7(4) . . ? F9A P2 F10B 119.8(3) . . ? C8 O9 C10 112.4(3) . . ? C13 O12 C11 113.6(3) . . ? C2 N1 C5 107.5(4) . . ? C2 N1 C6 126.7(4) . . ? C5 N1 C6 125.6(4) . . ? C2 N3 C4 107.7(4) . . ? C2 N3 C7 126.3(4) . . ? C4 N3 C7 126.0(4) . . ? C16 N15 C19 108.4(3) . . ? C16 N15 C14 125.4(3) . . ? C19 N15 C14 126.1(3) . . ? C16 N17 C18 107.9(3) . . ? C16 N17 C20 126.2(3) . . ? C18 N17 C20 126.0(3) . . ? N3 C2 N1 109.9(4) . . ? C5 C4 N3 107.3(4) . . ? C4 C5 N1 107.7(5) . . ? N3 C7 C8 111.7(4) . . ? O9 C8 C7 108.0(3) . . ? O9 C10 C11 108.4(3) . . ? O12 C11 C10 109.1(3) . . ? O12 C13 C14 108.7(3) . . ? N15 C14 C13 110.5(4) . . ? N17 C16 N15 109.5(3) . . ? C19 C18 N17 107.5(4) . . ? C18 C19 N15 106.7(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 N3 C7 C8 -83.9(5) . . . . ? C4 N3 C7 C8 94.1(5) . . . . ? N3 C7 C8 O9 65.0(5) . . . . ? C7 C8 O9 C10 -168.0(4) . . . . ? C8 O9 C10 C11 179.9(4) . . . . ? O9 C10 C11 O12 74.5(4) . . . . ? C10 C11 O12 C13 -179.5(3) . . . . ? C11 O12 C13 C14 -151.7(3) . . . . ? O12 C13 C14 N15 61.9(4) . . . . ? C13 C14 N15 C16 -114.6(4) . . . . ? C13 C14 N15 C19 61.3(5) . . . . ? _diffrn_measured_fraction_theta_max 0.942 _diffrn_reflns_theta_full 23.29 _diffrn_measured_fraction_theta_full 0.942 _refine_diff_density_max 0.392 _refine_diff_density_min -0.202 _refine_diff_density_rms 0.049 #===END data_r1 _database_code_CSD 202390 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,1'-(1,10-decyl)-bis(3-methylimidazolium) hexafluorophosphate ; _chemical_name_common "1,1'-(1,10-decyl)-bis(3-methylimidazolium) hexafluorophosphate" _chemical_melting_point 344K _chemical_formula_moiety ? _chemical_formula_sum 'C18 H32 F12 N4 P2' _chemical_formula_weight 594.42 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 '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 6.4611(2) _cell_length_b 16.5436(5) _cell_length_c 12.1828(4) _cell_angle_alpha 90.00 _cell_angle_beta 99.4450(10) _cell_angle_gamma 90.00 _cell_volume 1284.56(7) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour colorless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.537 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 612 _exptl_absorpt_coefficient_mu 0.271 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8031 _diffrn_reflns_av_R_equivalents 0.0149 _diffrn_reflns_av_sigmaI/netI 0.0202 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 27.97 _reflns_number_total 2990 _reflns_number_gt 2639 _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 'calc w=1/[\s^2^(Fo^2^)+(0.0517P)^2^+0.4591P] 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 0.0022(15) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2990 _refine_ls_number_parameters 165 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0421 _refine_ls_R_factor_gt 0.0364 _refine_ls_wR_factor_ref 0.1015 _refine_ls_wR_factor_gt 0.0965 _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_restrained_S_all 1.069 _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 P P 0.19278(6) 0.70623(2) 0.14651(3) 0.02653(13) Uani 1 1 d . . . F1 F 0.20852(16) 0.77090(6) 0.24475(9) 0.0469(3) Uani 1 1 d . . . F2 F 0.1514(2) 0.77678(6) 0.05704(10) 0.0546(3) Uani 1 1 d . . . F3 F 0.23293(17) 0.63466(6) 0.23523(9) 0.0475(3) Uani 1 1 d . . . F4 F 0.44048(15) 0.71307(7) 0.14903(9) 0.0475(3) Uani 1 1 d . . . F5 F 0.17705(17) 0.64149(6) 0.04765(8) 0.0461(3) Uani 1 1 d . . . F6 F -0.05455(15) 0.69822(6) 0.14570(8) 0.0426(3) Uani 1 1 d . . . N1 N -0.31971(18) 0.81437(7) 0.39776(9) 0.0254(2) Uani 1 1 d . . . N2 N -0.17456(17) 0.90686(7) 0.31135(9) 0.0241(2) Uani 1 1 d . . . C1 C -0.2141(2) 0.82811(8) 0.31557(11) 0.0267(3) Uani 1 1 d . . . H1A H -0.1731 0.7882 0.2673 0.032 Uiso 1 1 calc R . . C2 C -0.2591(2) 0.94468(8) 0.39474(12) 0.0283(3) Uani 1 1 d . . . H2A H -0.2543 1.0008 0.4112 0.034 Uiso 1 1 calc R . . C3 C -0.3501(2) 0.88660(8) 0.44852(12) 0.0283(3) Uani 1 1 d . . . H3A H -0.4217 0.8942 0.5099 0.034 Uiso 1 1 calc R . . C4 C -0.3866(3) 0.73427(9) 0.42986(13) 0.0339(3) Uani 1 1 d . . . H4A H -0.3650 0.6946 0.3730 0.051 Uiso 1 1 calc R . . H4B H -0.5357 0.7359 0.4365 0.051 Uiso 1 1 calc R . . H4C H -0.3040 0.7187 0.5015 0.051 Uiso 1 1 calc R . . C5 C -0.0603(2) 0.94603(8) 0.23078(11) 0.0271(3) Uani 1 1 d . . . H5A H -0.1496 0.9887 0.1904 0.033 Uiso 1 1 calc R . . H5B H -0.0306 0.9055 0.1756 0.033 Uiso 1 1 calc R . . C6 C 0.1444(2) 0.98323(9) 0.28699(11) 0.0291(3) Uani 1 1 d . . . H6A H 0.2389 0.9399 0.3218 0.035 Uiso 1 1 calc R . . H6B H 0.1163 1.0203 0.3466 0.035 Uiso 1 1 calc R . . C7 C 0.2528(2) 1.02988(9) 0.20424(12) 0.0304(3) Uani 1 1 d . . . H7A H 0.1522 1.0695 0.1649 0.036 Uiso 1 1 calc R . . H7B H 0.3715 1.0606 0.2462 0.036 Uiso 1 1 calc R . . C8 C 0.3355(2) 0.97739(8) 0.11785(12) 0.0283(3) Uani 1 1 d . . . H8A H 0.4320 0.9362 0.1567 0.034 Uiso 1 1 calc R . . H8B H 0.2163 0.9487 0.0729 0.034 Uiso 1 1 calc R . . C9 C 0.4508(2) 1.02613(8) 0.04049(11) 0.0250(3) Uani 1 1 d . . . H9A H 0.5626 1.0583 0.0860 0.030 Uiso 1 1 calc R . . H9B H 0.3511 1.0644 -0.0026 0.030 Uiso 1 1 calc R . . 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 P 0.0280(2) 0.02294(19) 0.0289(2) -0.00129(13) 0.00537(14) 0.00253(13) F1 0.0445(5) 0.0468(6) 0.0477(6) -0.0224(5) 0.0021(4) 0.0033(4) F2 0.0709(8) 0.0384(6) 0.0523(6) 0.0177(5) 0.0031(5) 0.0022(5) F3 0.0516(6) 0.0424(5) 0.0470(6) 0.0172(4) 0.0033(5) 0.0015(4) F4 0.0319(5) 0.0602(7) 0.0524(6) -0.0028(5) 0.0130(4) -0.0032(4) F5 0.0533(6) 0.0430(6) 0.0423(5) -0.0167(4) 0.0082(5) 0.0061(4) F6 0.0286(5) 0.0538(6) 0.0451(6) -0.0100(4) 0.0048(4) 0.0007(4) N1 0.0278(6) 0.0219(5) 0.0265(6) -0.0010(4) 0.0050(5) -0.0022(4) N2 0.0261(5) 0.0228(5) 0.0241(5) -0.0001(4) 0.0060(4) -0.0006(4) C1 0.0290(7) 0.0236(6) 0.0282(7) -0.0034(5) 0.0070(5) -0.0015(5) C2 0.0327(7) 0.0225(6) 0.0312(7) -0.0014(5) 0.0096(6) 0.0026(5) C3 0.0322(7) 0.0253(6) 0.0292(7) -0.0026(5) 0.0108(6) 0.0010(5) C4 0.0445(8) 0.0237(7) 0.0341(8) 0.0000(6) 0.0087(6) -0.0095(6) C5 0.0294(7) 0.0298(7) 0.0228(6) 0.0025(5) 0.0059(5) -0.0029(5) C6 0.0295(7) 0.0338(7) 0.0246(6) -0.0022(5) 0.0061(5) -0.0045(6) C7 0.0341(7) 0.0283(7) 0.0307(7) -0.0044(5) 0.0114(6) -0.0071(6) C8 0.0322(7) 0.0242(6) 0.0302(7) -0.0016(5) 0.0101(6) -0.0033(5) C9 0.0284(6) 0.0216(6) 0.0257(6) -0.0015(5) 0.0066(5) -0.0011(5) _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 P F2 1.5894(10) . ? P F3 1.5955(10) . ? P F1 1.5960(9) . ? P F4 1.5996(10) . ? P F6 1.6019(10) . ? P F5 1.6025(9) . ? N1 C1 1.3205(18) . ? N1 C3 1.3744(17) . ? N1 C4 1.4668(17) . ? N2 C1 1.3303(17) . ? N2 C2 1.3800(17) . ? N2 C5 1.4720(16) . ? C2 C3 1.3506(19) . ? C5 C6 1.5165(19) . ? C6 C7 1.5275(19) . ? C7 C8 1.5270(19) . ? C8 C9 1.5246(18) . ? C9 C9 1.526(2) 3_675 ? 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 F2 P F3 179.30(6) . . ? F2 P F1 90.28(6) . . ? F3 P F1 90.36(6) . . ? F2 P F4 90.95(6) . . ? F3 P F4 89.34(6) . . ? F1 P F4 89.87(6) . . ? F2 P F6 90.06(6) . . ? F3 P F6 89.65(6) . . ? F1 P F6 90.05(5) . . ? F4 P F6 178.99(6) . . ? F2 P F5 89.57(6) . . ? F3 P F5 89.79(6) . . ? F1 P F5 179.85(6) . . ? F4 P F5 90.09(6) . . ? F6 P F5 89.99(5) . . ? C1 N1 C3 108.74(11) . . ? C1 N1 C4 124.71(12) . . ? C3 N1 C4 126.54(12) . . ? C1 N2 C2 108.29(11) . . ? C1 N2 C5 125.28(12) . . ? C2 N2 C5 126.44(11) . . ? N1 C1 N2 108.93(12) . . ? C3 C2 N2 106.92(12) . . ? C2 C3 N1 107.13(12) . . ? N2 C5 C6 111.92(11) . . ? C5 C6 C7 111.54(11) . . ? C8 C7 C6 114.69(11) . . ? C9 C8 C7 112.78(11) . . ? C8 C9 C9 113.42(13) . 3_675 ? _diffrn_measured_fraction_theta_max 0.965 _diffrn_reflns_theta_full 27.97 _diffrn_measured_fraction_theta_full 0.965 _refine_diff_density_max 0.355 _refine_diff_density_min -0.352 _refine_diff_density_rms 0.053 #===END data_g1 _database_code_CSD 202391 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H44 Hg N4 O11 S2' _chemical_formula_weight 901.40 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' Hg Hg -2.3894 9.2266 '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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.086(3) _cell_length_b 12.459(3) _cell_length_c 15.204(4) _cell_angle_alpha 83.209(4) _cell_angle_beta 84.160(4) _cell_angle_gamma 67.666(5) _cell_volume 1751.4(8) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 974 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.709 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 904 _exptl_absorpt_coefficient_mu 4.576 _exptl_absorpt_correction_type SADABS _exptl_absorpt_correction_T_min 0.511978 _exptl_absorpt_correction_T_max 0.970265 _exptl_absorpt_process_details ; 2-theta dependent absorption corrections applied for an effective sphere with mu*diameter = 0.040 ; _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 '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 7935 _diffrn_reflns_av_R_equivalents 0.0407 _diffrn_reflns_av_sigmaI/netI 0.0393 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 23.30 _reflns_number_total 5002 _reflns_number_gt 4540 _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 ; calc w=3D1/[\s^2^(Fo^2^)+(0.0712P)^2^+0.0000P] where P=3D(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 5002 _refine_ls_number_parameters 565 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0409 _refine_ls_R_factor_gt 0.0369 _refine_ls_wR_factor_ref 0.0909 _refine_ls_wR_factor_gt 0.0895 _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_restrained_S_all 1.016 _refine_ls_shift/su_max 0.912 _refine_ls_shift/su_mean 0.002 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 Hg Hg 0.84192(2) 0.757029(18) 0.679262(14) 0.02131(11) Uani 1 1 d . . . S1 S 0.54953(15) 0.59918(13) 0.68155(11) 0.0263(3) Uani 1 1 d . . . S2 S 0.85841(16) 0.80564(14) 1.16335(10) 0.0257(3) Uani 1 1 d . . . O1 O 0.5689(5) 0.5034(5) 0.6305(3) 0.0476(13) Uani 1 1 d . . . O2 O 0.4586(5) 0.7085(4) 0.6374(3) 0.0496(14) Uani 1 1 d . . . O3 O 0.6831(5) 0.6011(5) 0.7045(3) 0.0479(13) Uani 1 1 d . . . O4 O 0.7756(5) 0.9054(4) 1.1068(3) 0.0389(11) Uani 1 1 d . . . O5 O 0.8748(5) 0.6963(4) 1.1295(3) 0.0349(11) Uani 1 1 d . . . O6 O 0.8104(5) 0.8106(5) 1.2560(3) 0.0384(12) Uani 1 1 d . . . O7 O 0.4530(8) 0.6850(7) 0.4433(5) 0.0660(19) Uani 1 1 d . . . H1O7 H 0.449(11) 0.626(10) 0.427(7) 0.08(4) Uiso 1 1 d . . . H2O7 H 0.451(11) 0.674(9) 0.492(7) 0.06(4) Uiso 1 1 d . . . O8 O 1.0309(6) 0.4881(4) 1.2361(4) 0.0376(12) Uani 1 1 d . . . H1O8 H 0.992(7) 0.556(7) 1.197(5) 0.037(19) Uiso 1 1 d . . . H2O8 H 1.098(12) 0.482(11) 1.249(8) 0.10(5) Uiso 1 1 d . . . O9 O 1.0505(4) 0.7891(4) 0.7741(3) 0.0288(10) Uani 1 1 d . . . O12 O 0.9306(4) 0.9583(4) 0.6287(3) 0.0302(10) Uani 1 1 d . . . O15 O 0.7145(4) 0.9364(4) 0.5359(3) 0.0270(9) Uani 1 1 d . . . N1 N 0.5861(5) 0.8830(4) 0.8041(3) 0.0197(10) Uani 1 1 d . . . N3 N 0.7748(5) 0.7919(4) 0.8771(3) 0.0219(11) Uani 1 1 d . . . N18 N 0.8672(5) 0.6980(4) 0.4895(3) 0.0230(11) Uani 1 1 d . . . N20 N 1.0760(5) 0.6255(5) 0.5414(3) 0.0258(12) Uani 1 1 d . . . C2 C 0.7273(6) 0.8181(5) 0.7946(4) 0.0223(13) Uani 1 1 d . . . C4 C 0.6632(7) 0.8403(6) 0.9384(4) 0.0271(14) Uani 1 1 d . . . H4A H 0.681(6) 0.830(5) 0.998(4) 0.017(15) Uiso 1 1 d . . . C5 C 0.5459(7) 0.8973(6) 0.8924(4) 0.0265(14) Uani 1 1 d . . . H5A H 0.460(6) 0.934(5) 0.905(3) 0.000(13) Uiso 1 1 d . . . C6 C 0.4895(6) 0.9309(6) 0.7310(4) 0.0297(14) Uani 1 1 d . . . H6A H 0.5433 0.9481 0.6775 0.045 Uiso 1 1 calc R . . H6B H 0.4113 1.0027 0.7474 0.045 Uiso 1 1 calc R . . H6C H 0.4494 0.8739 0.7195 0.045 Uiso 1 1 calc R . . C7 C 0.9247(7) 0.7275(6) 0.8993(5) 0.0276(14) Uani 1 1 d . . . H7A H 0.957(6) 0.660(6) 0.866(4) 0.020(15) Uiso 1 1 d . . . H7B H 0.930(5) 0.715(5) 0.962(4) 0.008(13) Uiso 1 1 d . . . C8 C 1.0177(7) 0.7989(6) 0.8675(4) 0.0276(14) Uani 1 1 d . . . H8A H 0.961(6) 0.869(5) 0.882(4) 0.010(13) Uiso 1 1 d . . . H8B H 1.115(7) 0.764(6) 0.903(4) 0.033(17) Uiso 1 1 d . . . C10 C 1.1083(7) 0.8731(6) 0.7344(5) 0.0311(15) Uani 1 1 d . . . H10A H 1.161(6) 0.888(5) 0.775(4) 0.019(15) Uiso 1 1 d . . . H10B H 1.166(8) 0.843(7) 0.688(6) 0.05(2) Uiso 1 1 d . . . C11 C 0.9917(7) 0.9837(6) 0.6997(5) 0.0301(15) Uani 1 1 d . . . H11A H 0.915(6) 1.017(5) 0.742(4) 0.021(15) Uiso 1 1 d . . . H11B H 1.036(8) 1.050(7) 0.669(5) 0.06(2) Uiso 1 1 d . . . C13 C 0.8097(8) 1.0575(6) 0.5976(5) 0.0359(16) Uani 1 1 d . . . H13A H 0.839(6) 1.128(6) 0.586(4) 0.019(15) Uiso 1 1 d . . . H13B H 0.742(9) 1.063(7) 0.646(6) 0.06(2) Uiso 1 1 d . . . C14 C 0.7664(9) 1.0289(7) 0.5155(5) 0.0382(17) Uani 1 1 d . . . H14B H 0.702(7) 1.084(6) 0.494(4) 0.024(18) Uiso 1 1 d . . . H14A H 0.850(7) 0.992(6) 0.472(4) 0.030(17) Uiso 1 1 d . . . C16 C 0.6850(7) 0.8931(6) 0.4613(4) 0.0287(15) Uani 1 1 d . . . H16A H 0.734(6) 0.912(5) 0.413(4) 0.006(13) Uiso 1 1 d . . . H16B H 0.600(7) 0.933(5) 0.441(4) 0.019(15) Uiso 1 1 d . . . C17 C 0.7127(6) 0.7666(6) 0.4797(5) 0.0307(15) Uani 1 1 d . . . H17A H 0.683(5) 0.728(5) 0.537(4) 0.008(13) Uiso 1 1 d . . . H17B H 0.687(7) 0.727(6) 0.432(5) 0.033(18) Uiso 1 1 d . . . C19 C 0.9377(6) 0.6883(5) 0.5622(4) 0.0198(12) Uani 1 1 d . . . C21 C 1.0914(8) 0.5959(6) 0.4560(5) 0.0314(17) Uani 1 1 d . . . H21A H 1.152(7) 0.561(5) 0.433(4) 0.007(16) Uiso 1 1 d . . . C22 C 0.9618(7) 0.6409(6) 0.4233(4) 0.0296(15) Uani 1 1 d . . . H22A H 0.930(6) 0.640(5) 0.371(4) 0.014(15) Uiso 1 1 d . . . C23 C 1.1914(7) 0.5910(7) 0.6029(5) 0.0404(18) Uani 1 1 d . . . H23A H 1.1506 0.5891 0.6641 0.061 Uiso 1 1 calc R . . H23B H 1.2389 0.6473 0.5943 0.061 Uiso 1 1 calc R . . H23C H 1.2616 0.5135 0.5912 0.061 Uiso 1 1 calc R . . C24 C 0.4556(6) 0.5774(5) 0.7828(4) 0.0232(13) Uani 1 1 d . . . C25 C 0.4574(7) 0.6367(6) 0.8546(4) 0.0286(14) Uani 1 1 d . . . H25A H 0.508(6) 0.686(6) 0.843(4) 0.022(16) Uiso 1 1 d . . . C26 C 0.3834(7) 0.6209(6) 0.9341(5) 0.0342(16) Uani 1 1 d . . . H26A H 0.397(6) 0.661(5) 0.977(4) 0.019(15) Uiso 1 1 d . . . C27 C 0.3085(6) 0.5465(5) 0.9437(4) 0.0328(16) Uani 1 1 d . . . C28 C 0.3075(7) 0.4900(6) 0.8716(5) 0.0335(16) Uani 1 1 d . . . H28A H 0.261(7) 0.438(6) 0.880(5) 0.035(19) Uiso 1 1 d . . . C29 C 0.3812(6) 0.5044(6) 0.7914(5) 0.0295(15) Uani 1 1 d . . . H29A H 0.378(6) 0.464(5) 0.744(4) 0.015(14) Uiso 1 1 d . . . C30 C 0.2292(8) 0.5294(7) 1.0299(5) 0.052(2) Uani 1 1 d . . . H30A H 0.2580 0.4459 1.0480 0.079 Uiso 1 1 calc R . . H30B H 0.1256 0.5633 1.0224 0.079 Uiso 1 1 calc R . . H30C H 0.2521 0.5677 1.0756 0.079 Uiso 1 1 calc R . . C31 C 1.0353(6) 0.8069(5) 1.1564(4) 0.0228(13) Uani 1 1 d . . . C32 C 1.0778(8) 0.8735(6) 1.0898(5) 0.0333(16) Uani 1 1 d . . . H32A H 1.017(8) 0.915(7) 1.048(5) 0.04(2) Uiso 1 1 d . . . C33 C 1.2168(8) 0.8739(6) 1.0854(6) 0.0420(19) Uani 1 1 d . . . H33A H 1.232(8) 0.909(8) 1.034(6) 0.06(2) Uiso 1 1 d . . . C34 C 1.3125(7) 0.8089(6) 1.1493(5) 0.0364(17) Uani 1 1 d . . . C35 C 1.2670(7) 0.7417(6) 1.2149(5) 0.0316(15) Uani 1 1 d . . . H35A H 1.322(8) 0.707(7) 1.259(5) 0.05(2) Uiso 1 1 d . . . C36 C 1.1310(6) 0.7403(5) 1.2189(4) 0.0248(14) Uani 1 1 d . . . H36A H 1.105(7) 0.701(6) 1.262(5) 0.034(19) Uiso 1 1 d . . . C37 C 1.4605(8) 0.8121(7) 1.1470(8) 0.069(3) Uani 1 1 d . . . H37A H 1.4910 0.8011 1.2077 0.103 Uiso 1 1 calc R . . H37B H 1.4590 0.8875 1.1191 0.103 Uiso 1 1 calc R . . H37C H 1.5279 0.7497 1.1127 0.103 Uiso 1 1 calc R . . 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 Hg 0.01966(15) 0.02022(15) 0.02150(16) -0.00233(9) -0.00081(9) -0.00455(10) S1 0.0227(7) 0.0230(8) 0.0324(9) -0.0013(7) 0.0023(6) -0.0087(6) S2 0.0226(7) 0.0253(8) 0.0263(8) -0.0017(6) -0.0058(6) -0.0048(6) O1 0.054(3) 0.048(3) 0.048(3) -0.021(3) 0.014(2) -0.027(3) O2 0.044(3) 0.039(3) 0.044(3) 0.013(2) 0.006(2) 0.001(2) O3 0.034(3) 0.073(4) 0.049(3) 0.002(3) -0.003(2) -0.037(3) O4 0.038(2) 0.031(3) 0.041(3) 0.006(2) -0.017(2) -0.005(2) O5 0.031(2) 0.029(2) 0.047(3) -0.006(2) -0.004(2) -0.012(2) O6 0.025(2) 0.058(3) 0.028(3) -0.006(2) 0.0009(19) -0.010(2) O7 0.099(5) 0.069(5) 0.054(5) -0.001(4) -0.018(4) -0.055(4) O8 0.037(3) 0.026(3) 0.051(3) 0.007(2) -0.008(2) -0.014(2) O9 0.030(2) 0.024(2) 0.034(3) -0.0024(19) -0.0059(19) -0.0099(19) O12 0.034(2) 0.020(2) 0.035(3) 0.0011(19) -0.0070(19) -0.0088(19) O15 0.028(2) 0.025(2) 0.025(2) -0.0010(18) -0.0003(18) -0.0067(18) N1 0.017(2) 0.018(3) 0.024(3) -0.002(2) 0.001(2) -0.007(2) N3 0.024(3) 0.020(3) 0.020(3) -0.002(2) -0.003(2) -0.006(2) N18 0.020(2) 0.023(3) 0.024(3) -0.001(2) 0.002(2) -0.006(2) N20 0.018(3) 0.029(3) 0.027(3) -0.003(2) 0.007(2) -0.006(2) C2 0.026(3) 0.018(3) 0.022(3) 0.000(2) 0.001(3) -0.008(3) C4 0.032(4) 0.029(4) 0.021(4) -0.003(3) 0.001(3) -0.013(3) C5 0.019(3) 0.025(3) 0.034(4) -0.004(3) 0.002(3) -0.007(3) C6 0.022(3) 0.035(4) 0.031(4) 0.002(3) -0.004(3) -0.009(3) C7 0.028(3) 0.024(3) 0.025(4) 0.002(3) -0.008(3) -0.003(3) C8 0.027(3) 0.017(3) 0.034(4) -0.004(3) -0.007(3) -0.001(3) C10 0.022(3) 0.038(4) 0.036(4) -0.004(3) -0.003(3) -0.014(3) C11 0.030(3) 0.028(4) 0.035(4) -0.008(3) 0.004(3) -0.014(3) C13 0.043(4) 0.018(3) 0.044(4) 0.004(3) -0.007(3) -0.010(3) C14 0.044(4) 0.027(4) 0.040(4) 0.013(3) -0.009(4) -0.012(4) C16 0.022(3) 0.035(4) 0.020(3) -0.001(3) -0.002(3) -0.002(3) C17 0.021(3) 0.046(4) 0.026(4) -0.007(3) 0.002(3) -0.012(3) C19 0.019(3) 0.018(3) 0.022(3) 0.002(2) -0.002(2) -0.007(2) C21 0.029(4) 0.027(4) 0.032(4) -0.007(3) 0.014(3) -0.005(3) C22 0.038(4) 0.028(4) 0.020(4) 0.000(3) 0.006(3) -0.012(3) C23 0.020(3) 0.041(4) 0.052(5) 0.000(4) -0.005(3) -0.003(3) C24 0.017(3) 0.017(3) 0.031(3) 0.001(3) -0.005(2) -0.002(2) C25 0.026(3) 0.024(3) 0.036(4) -0.001(3) -0.003(3) -0.010(3) C26 0.032(4) 0.036(4) 0.032(4) -0.004(3) -0.003(3) -0.009(3) C27 0.023(3) 0.022(3) 0.036(4) 0.004(3) 0.002(3) 0.009(3) C28 0.021(3) 0.029(4) 0.046(4) 0.007(3) -0.003(3) -0.007(3) C29 0.026(3) 0.023(3) 0.042(4) -0.006(3) -0.001(3) -0.010(3) C30 0.038(4) 0.050(5) 0.050(5) 0.009(4) 0.011(4) -0.003(4) C31 0.028(3) 0.015(3) 0.024(3) -0.003(3) -0.001(3) -0.006(2) C32 0.046(4) 0.016(3) 0.031(4) 0.001(3) 0.002(3) -0.005(3) C33 0.050(5) 0.025(4) 0.049(5) 0.001(3) 0.020(4) -0.019(3) C34 0.031(3) 0.021(3) 0.057(5) -0.011(3) 0.014(3) -0.011(3) C35 0.024(3) 0.021(3) 0.049(4) 0.000(3) -0.003(3) -0.009(3) C36 0.029(3) 0.017(3) 0.028(4) 0.007(3) 0.000(3) -0.011(3) C37 0.031(4) 0.037(5) 0.139(9) 0.004(5) 0.019(5) -0.022(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 Hg C19 2.054(6) . ? Hg C2 2.055(6) . ? S1 O3 1.435(5) . ? S1 O1 1.441(5) . ? S1 O2 1.452(5) . ? S1 C24 1.772(6) . ? S2 O6 1.443(5) . ? S2 O4 1.444(5) . ? S2 O5 1.458(5) . ? S2 C31 1.782(6) . ? O9 C10 1.429(8) . ? O9 C8 1.433(8) . ? O12 C11 1.418(8) . ? O12 C13 1.440(8) . ? O15 C16 1.415(8) . ? O15 C14 1.427(9) . ? N1 C2 1.347(7) . ? N1 C5 1.374(8) . ? N1 C6 1.470(8) . ? N3 C2 1.348(8) . ? N3 C4 1.380(8) . ? N3 C7 1.470(8) . ? N18 C19 1.344(8) . ? N18 C22 1.373(8) . ? N18 C17 1.478(8) . ? N20 C19 1.340(7) . ? N20 C21 1.370(9) . ? N20 C23 1.469(9) . ? C4 C5 1.344(10) . ? C7 C8 1.531(10) . ? C10 C11 1.511(10) . ? C13 C14 1.487(11) . ? C16 C17 1.490(10) . ? C21 C22 1.334(10) . ? C24 C29 1.371(9) . ? C24 C25 1.394(9) . ? C25 C26 1.389(10) . ? C26 C27 1.389(10) . ? C27 C28 1.374(10) . ? C27 C30 1.501(10) . ? C28 C29 1.393(10) . ? C31 C32 1.372(9) . ? C31 C36 1.383(9) . ? C32 C33 1.398(11) . ? C33 C34 1.393(12) . ? C34 C35 1.381(10) . ? C34 C37 1.505(10) . ? C35 C36 1.374(9) . ? 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 C19 Hg C2 173.1(2) . . ? O3 S1 O1 112.6(3) . . ? O3 S1 O2 113.1(3) . . ? O1 S1 O2 110.7(3) . . ? O3 S1 C24 106.5(3) . . ? O1 S1 C24 106.7(3) . . ? O2 S1 C24 106.7(3) . . ? O6 S2 O4 114.2(3) . . ? O6 S2 O5 112.8(3) . . ? O4 S2 O5 111.9(3) . . ? O6 S2 C31 106.0(3) . . ? O4 S2 C31 105.9(3) . . ? O5 S2 C31 105.0(3) . . ? C10 O9 C8 111.7(5) . . ? C11 O12 C13 111.6(5) . . ? C16 O15 C14 114.9(5) . . ? C2 N1 C5 109.8(5) . . ? C2 N1 C6 125.1(5) . . ? C5 N1 C6 125.1(5) . . ? C2 N3 C4 110.1(5) . . ? C2 N3 C7 125.6(5) . . ? C4 N3 C7 124.3(5) . . ? C19 N18 C22 109.9(5) . . ? C19 N18 C17 125.2(5) . . ? C22 N18 C17 124.8(5) . . ? C19 N20 C21 109.7(5) . . ? C19 N20 C23 124.5(5) . . ? C21 N20 C23 125.8(5) . . ? N1 C2 N3 106.0(5) . . ? N1 C2 Hg 126.8(4) . . ? N3 C2 Hg 126.9(4) . . ? C5 C4 N3 106.6(6) . . ? C4 C5 N1 107.5(6) . . ? N3 C7 C8 111.0(5) . . ? O9 C8 C7 107.5(5) . . ? O9 C10 C11 111.4(5) . . ? O12 C11 C10 108.5(5) . . ? O12 C13 C14 107.8(6) . . ? O15 C14 C13 109.9(6) . . ? O15 C16 C17 110.1(5) . . ? N18 C17 C16 111.1(5) . . ? N20 C19 N18 106.1(5) . . ? N20 C19 Hg 129.5(4) . . ? N18 C19 Hg 124.4(4) . . ? C22 C21 N20 107.6(6) . . ? C21 C22 N18 106.8(6) . . ? C29 C24 C25 119.8(6) . . ? C29 C24 S1 121.4(5) . . ? C25 C24 S1 118.9(5) . . ? C26 C25 C24 119.4(7) . . ? C27 C26 C25 121.3(7) . . ? C28 C27 C26 118.0(6) . . ? C28 C27 C30 120.8(7) . . ? C26 C27 C30 121.1(7) . . ? C27 C28 C29 121.6(7) . . ? C24 C29 C28 119.9(6) . . ? C32 C31 C36 119.4(6) . . ? C32 C31 S2 120.7(5) . . ? C36 C31 S2 119.8(5) . . ? C31 C32 C33 120.1(7) . . ? C34 C33 C32 120.6(7) . . ? C35 C34 C33 117.8(6) . . ? C35 C34 C37 121.1(7) . . ? C33 C34 C37 121.1(7) . . ? C36 C35 C34 121.6(7) . . ? C35 C36 C31 120.4(6) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 N3 C7 C8 68.1(8) . . . . ? C4 N3 C7 C8 -107.9(7) . . . . ? N3 C7 C8 O9 -79.1(6) . . . . ? C7 C8 O9 C10 166.6(5) . . . . ? C8 O9 C10 C11 -91.6(6) . . . . ? O9 C10 C11 O12 -66.0(7) . . . . ? C10 C11 O12 C13 174.8(6) . . . . ? C11 O12 C13 C14 171.8(6) . . . . ? O12 C13 C14 O15 65.4(8) . . . . ? C13 C14 O15 C16 -173.4(5) . . . . ? C14 O15 C16 C17 148.1(6) . . . . ? O15 C16 C17 N18 -66.4(7) . . . . ? C16 C17 N18 C22 -97.4(7) . . . . ? C19 N18 C17 C16 78.0(7) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 23.30 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 1.634 _refine_diff_density_min -1.505 _refine_diff_density_rms 0.145 #===END