# Supplementary Material (ESI) for New Journal of Chemistry # This journal is (c) The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2008 data_global _journal_name_full 'New J.Chem.' _journal_coden_Cambridge 0440 _publ_contact_author_name 'Reinaldo Goncalves' _publ_contact_author_email REINALDO@IQ.UFRGS.BR _publ_section_title ; Electrochemical methodology for determination of imidazolium ionic liquids (solids at room temperature) properties: Influence of the temperature ; _publ_requested_category FO loop_ _publ_author_name 'Reinaldo Goncalves' 'D. Back' 'Jairton Dupont' 'Ernesto Schulz Lang' 'Elizeo Lissner' 'M.V. Migliorini' ; H.S.Schrekker ; 'Marcelo Stracke' # Attachment 'checkcif_fig6a.txt' data_marcelo _database_code_depnum_ccdc_archive 'CCDC 607218' _audit_creation_date 2006-05-11T21:22:27-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; (Ph2CHCH2Ph)[(CF3SO2)2N] ; _chemical_formula_moiety 'C20 H19 F6 N3 O4 S2' _chemical_formula_sum 'C20 H19 F6 N3 O4 S2' _chemical_formula_weight 543.5 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _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 10.0301(9) _cell_length_b 18.8620(19) _cell_length_c 12.9786(12) _cell_angle_alpha 90 _cell_angle_beta 93.289(6) _cell_angle_gamma 90 _cell_volume 2451.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 173 _cell_measurement_theta_min 4 _cell_measurement_theta_max 30 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.15 _exptl_crystal_density_diffrn 1.473 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1112 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.294 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details SADABS _exptl_absorpt_correction_T_min 0.9327 _exptl_absorpt_correction_T_max 1 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi scan' _diffrn_reflns_av_R_equivalents 0.0578 _diffrn_reflns_av_unetI/netI 0.0708 _diffrn_reflns_number 29841 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.64 _diffrn_reflns_theta_max 29.58 _diffrn_reflns_theta_full 29.58 _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.994 _reflns_number_total 6838 _reflns_number_gt 2503 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker APEX2/BIS/COSMO' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT/SADABS' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Crysal Impact Diamond 3' _computing_publication_material WinGX #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.1739P)^2^+0.0000P] 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_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.015(3) _refine_ls_number_reflns 6838 _refine_ls_number_parameters 381 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1779 _refine_ls_R_factor_gt 0.078 _refine_ls_wR_factor_ref 0.2819 _refine_ls_wR_factor_gt 0.2326 _refine_ls_goodness_of_fit_ref 0.883 _refine_ls_restrained_S_all 0.883 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.548 _refine_diff_density_min -0.366 _refine_diff_density_rms 0.073 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C2 C 0.5787(3) 0.15009(19) 0.2855(3) 0.0684(9) Uani 1 1 d . . . H2 H 0.6207 0.1077 0.3045 0.082 Uiso 1 1 calc R . . C3 C 0.4280(4) 0.2271(2) 0.2349(3) 0.0773(10) Uani 1 1 d . . . H3 H 0.3467 0.2472 0.2127 0.093 Uiso 1 1 calc R . . C4 C 0.5429(4) 0.2612(2) 0.2521(3) 0.0790(10) Uani 1 1 d . . . H4 H 0.5571 0.3095 0.244 0.095 Uiso 1 1 calc R . . C1 C 0.7773(3) 0.22633(18) 0.3138(2) 0.0601(8) Uani 1 1 d . . . H1A H 0.819 0.2496 0.2572 0.072 Uiso 1 1 calc R . . H1B H 0.8238 0.182 0.328 0.072 Uiso 1 1 calc R . . C5 C 0.7893(3) 0.27363(16) 0.4096(2) 0.0530(7) Uani 1 1 d . . . H5 H 0.7433 0.3181 0.3912 0.064 Uiso 1 1 calc R . . C6 C 0.7212(3) 0.24319(16) 0.5009(2) 0.0531(7) Uani 1 1 d . . . C7 C 0.7468(3) 0.17602(17) 0.5386(2) 0.0634(8) Uani 1 1 d . . . H7 H 0.8065 0.147 0.5061 0.076 Uiso 1 1 calc R . . C8 C 0.6850(4) 0.1508(2) 0.6243(3) 0.0758(10) Uani 1 1 d . . . H8 H 0.7031 0.1054 0.6489 0.091 Uiso 1 1 calc R . . C9 C 0.5970(4) 0.1937(2) 0.6724(3) 0.0809(11) Uani 1 1 d . . . H9 H 0.555 0.1772 0.7298 0.097 Uiso 1 1 calc R . . C10 C 0.5710(4) 0.2606(2) 0.6359(3) 0.0861(12) Uani 1 1 d . . . H10 H 0.5121 0.2897 0.669 0.103 Uiso 1 1 calc R . . C11 C 0.6313(3) 0.28480(19) 0.5511(2) 0.0684(9) Uani 1 1 d . . . H11 H 0.6117 0.3301 0.5265 0.082 Uiso 1 1 calc R . . C12 C 0.9351(3) 0.29266(18) 0.4382(2) 0.0608(8) Uani 1 1 d . . . C13 C 0.9676(4) 0.3616(2) 0.4563(3) 0.0950(12) Uani 1 1 d . . . H13 H 0.9014 0.3961 0.4508 0.114 Uiso 1 1 calc R . . C14 C 1.0991(6) 0.3811(3) 0.4832(5) 0.1273(19) Uani 1 1 d . . . H14 H 1.121 0.4285 0.4942 0.153 Uiso 1 1 calc R . . C15 C 1.1941(5) 0.3308(4) 0.4931(4) 0.1256(19) Uani 1 1 d . . . H15 H 1.2816 0.3437 0.5119 0.151 Uiso 1 1 calc R . . C16 C 1.1644(4) 0.2623(3) 0.4763(4) 0.1065(14) Uani 1 1 d . . . H16 H 1.2309 0.228 0.4837 0.128 Uiso 1 1 calc R . . C17 C 1.0342(4) 0.2426(2) 0.4479(3) 0.0852(11) Uani 1 1 d . . . H17 H 1.014 0.1951 0.4354 0.102 Uiso 1 1 calc R . . C18 C 0.2960(10) 0.0523(3) 0.5411(5) 0.148(2) Uani 1 1 d . . . C20 C 0.3532(4) 0.0994(2) 0.2435(4) 0.1088(15) Uani 1 1 d . . . H20A H 0.2678 0.1189 0.2216 0.163 Uiso 1 1 calc R . . H20B H 0.3464 0.0753 0.3081 0.163 Uiso 1 1 calc R . . H20C H 0.3812 0.0666 0.1926 0.163 Uiso 1 1 calc R . . N1 N 0.6366(2) 0.21179(14) 0.28377(16) 0.0552(6) Uani 1 1 d . . . N2 N 0.4516(3) 0.15698(16) 0.2562(2) 0.0707(8) Uani 1 1 d . . . N3 N 0.2025(4) -0.01495(18) 0.7002(3) 0.0998(11) Uani 1 1 d . . . O11 O 0.2622(3) 0.11675(17) 0.7089(3) 0.1178(11) Uani 1 1 d . . . O12 O 0.4256(3) 0.02504(19) 0.7089(3) 0.1294(12) Uani 1 1 d . . . F1 F 0.3847(4) 0.1007(2) 0.5128(2) 0.1627(14) Uani 1 1 d . . . F2 F 0.1826(6) 0.0695(3) 0.5015(3) 0.218(3) Uani 1 1 d . . . F3 F 0.3290(8) -0.0060(3) 0.5036(3) 0.263(3) Uani 1 1 d . . . S1 S 0.29672(11) 0.04978(6) 0.68111(7) 0.0832(4) Uani 1 1 d . A . S2A S 0.04711(13) -0.00927(7) 0.70932(10) 0.0743(6) Uani 0.741(4) 1 d P A 1 O21A O -0.0126(4) 0.0537(2) 0.6667(4) 0.1147(15) Uani 0.741(4) 1 d P A 1 O22A O -0.0099(5) -0.0761(2) 0.6866(4) 0.1079(14) Uani 0.741(4) 1 d P A 1 C19A C 0.0293(12) 0.0013(5) 0.8480(7) 0.099(2) Uani 0.741(4) 1 d P A 1 F4A F -0.1014(9) 0.0021(8) 0.8642(9) 0.173(5) Uani 0.741(4) 1 d P A 1 F5A F 0.0875(8) 0.0575(3) 0.8831(4) 0.163(3) Uani 0.741(4) 1 d P A 1 F6A F 0.0795(9) -0.0547(4) 0.8970(5) 0.160(2) Uani 0.741(4) 1 d P A 1 S2B S 0.1245(9) -0.0043(4) 0.8254(6) 0.127(3) Uani 0.259(4) 1 d P A 2 F6B F -0.1050(16) -0.0043(13) 0.7172(16) 0.206(12) Uani 0.259(4) 1 d P A 2 F5B F -0.091(6) -0.030(2) 0.895(2) 0.28(3) Uani 0.259(4) 1 d P A 2 C19B C -0.050(6) 0.0164(19) 0.804(7) 0.24(4) Uani 0.259(4) 1 d P A 2 F4B F -0.068(2) 0.0710(17) 0.872(2) 0.239(11) Uani 0.259(4) 1 d P A 2 O21B O 0.139(3) -0.0726(12) 0.798(4) 0.31(2) Uani 0.259(4) 1 d P A 2 O22B O 0.1703(19) 0.0073(16) 0.9133(12) 0.154(8) Uani 0.259(4) 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 C2 0.066(2) 0.056(2) 0.083(2) 0.0037(16) -0.0059(17) 0.0030(17) C3 0.064(2) 0.072(3) 0.093(2) 0.0090(19) -0.0197(18) 0.0028(19) C4 0.079(3) 0.063(2) 0.092(2) 0.0149(18) -0.0177(19) 0.0073(19) C1 0.0518(19) 0.069(2) 0.0603(16) -0.0004(14) 0.0071(13) 0.0010(15) C5 0.0502(17) 0.0557(18) 0.0532(14) 0.0008(12) 0.0044(12) 0.0032(14) C6 0.0470(17) 0.0570(19) 0.0552(14) -0.0023(13) 0.0028(12) -0.0050(13) C7 0.067(2) 0.054(2) 0.0698(18) 0.0016(15) 0.0112(15) 0.0025(15) C8 0.088(3) 0.065(2) 0.076(2) 0.0037(16) 0.0099(19) -0.0161(19) C9 0.075(2) 0.099(3) 0.071(2) 0.002(2) 0.0231(18) -0.019(2) C10 0.065(2) 0.105(3) 0.092(2) 0.004(2) 0.0308(19) 0.011(2) C11 0.0542(19) 0.074(2) 0.079(2) 0.0058(16) 0.0146(16) 0.0103(16) C12 0.058(2) 0.066(2) 0.0588(16) 0.0061(14) 0.0047(14) -0.0103(16) C13 0.081(3) 0.077(3) 0.125(3) -0.008(2) -0.005(2) -0.014(2) C14 0.096(4) 0.095(4) 0.186(5) -0.019(3) -0.036(4) -0.039(3) C15 0.074(3) 0.154(6) 0.145(4) -0.007(4) -0.024(3) -0.029(4) C16 0.061(3) 0.111(4) 0.145(4) 0.014(3) -0.012(2) 0.002(3) C17 0.057(2) 0.083(3) 0.115(3) 0.004(2) 0.0028(19) -0.002(2) C18 0.232(8) 0.090(4) 0.124(5) -0.025(3) 0.027(5) -0.037(5) C20 0.092(3) 0.092(3) 0.138(4) 0.023(3) -0.031(3) -0.031(2) N1 0.0529(15) 0.0604(17) 0.0519(12) 0.0037(11) 0.0002(10) 0.0028(12) N2 0.0602(18) 0.074(2) 0.0759(16) 0.0103(14) -0.0125(13) -0.0094(14) N3 0.104(3) 0.067(2) 0.128(3) -0.0014(19) 0.001(2) 0.0082(19) O11 0.120(2) 0.085(2) 0.146(3) -0.0411(19) -0.0063(19) 0.0231(18) O12 0.094(2) 0.107(3) 0.185(3) 0.020(2) 0.001(2) 0.0288(19) F1 0.221(4) 0.150(3) 0.121(2) 0.006(2) 0.036(2) -0.047(3) F2 0.262(6) 0.255(6) 0.126(3) 0.016(3) -0.088(3) -0.060(5) F3 0.499(10) 0.144(4) 0.155(3) -0.075(3) 0.107(5) -0.056(5) S1 0.0938(8) 0.0697(7) 0.0857(6) -0.0098(5) 0.0016(5) -0.0101(5) S2A 0.0652(9) 0.0591(8) 0.0965(10) -0.0085(6) -0.0124(6) 0.0018(6) O21A 0.080(3) 0.106(3) 0.155(4) 0.026(3) -0.022(2) 0.018(2) O22A 0.096(3) 0.086(3) 0.140(3) -0.022(2) -0.011(2) -0.020(3) C19A 0.102(7) 0.085(6) 0.113(5) 0.000(4) 0.025(5) -0.011(5) F4A 0.128(5) 0.207(13) 0.191(9) -0.052(8) 0.076(5) -0.046(5) F5A 0.261(8) 0.113(4) 0.120(3) -0.052(3) 0.059(4) -0.082(5) F6A 0.192(6) 0.133(5) 0.151(4) 0.046(4) -0.025(4) -0.016(5) S2B 0.104(5) 0.133(6) 0.147(6) 0.043(4) 0.017(4) 0.010(4) F6B 0.106(11) 0.29(3) 0.218(18) 0.058(15) -0.051(11) -0.102(15) F5B 0.48(8) 0.25(3) 0.115(13) -0.013(17) 0.01(2) -0.17(4) C19B 0.17(5) 0.060(18) 0.49(12) 0.08(4) -0.04(7) 0.02(2) F4B 0.160(18) 0.25(3) 0.31(3) -0.05(2) 0.121(17) -0.038(18) O21B 0.36(4) 0.109(16) 0.49(6) 0.07(2) 0.21(4) 0.13(2) O22B 0.154(15) 0.22(2) 0.085(9) 0.014(11) -0.040(9) 0.023(17) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C2 N1 1.301(4) . ? C2 N2 1.316(4) . ? C3 C4 1.326(5) . ? C3 N2 1.370(4) . ? C4 N1 1.370(4) . ? C1 N1 1.469(4) . ? C1 C5 1.529(4) . ? C5 C6 1.514(4) . ? C5 C12 1.530(4) . ? C6 C7 1.377(4) . ? C6 C11 1.387(4) . ? C7 C8 1.387(4) . ? C8 C9 1.373(5) . ? C9 C10 1.368(5) . ? C10 C11 1.364(5) . ? C12 C13 1.357(5) . ? C12 C17 1.372(5) . ? C13 C14 1.395(6) . ? C14 C15 1.346(7) . ? C15 C16 1.341(7) . ? C16 C17 1.387(6) . ? C18 F3 1.254(7) . ? C18 F2 1.264(9) . ? C18 F1 1.342(7) . ? C18 S1 1.817(7) . ? C20 N2 1.470(5) . ? N3 S1 1.572(4) . ? N3 S2A 1.573(4) . ? N3 O21B 1.81(3) . ? N3 S2B 1.854(9) . ? O11 S1 1.364(3) . ? O12 S1 1.402(3) . ? S2A O22A 1.408(4) . ? S2A O21A 1.427(4) . ? S2A C19A 1.830(8) . ? C19A F5A 1.281(8) . ? C19A F6A 1.319(13) . ? C19A F4A 1.339(15) . ? S2B O22B 1.225(17) . ? S2B O21B 1.35(3) . ? S2B C19B 1.80(6) . ? F6B C19B 1.29(8) . ? F5B C19B 1.54(8) . ? C19B F4B 1.38(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 N1 C2 N2 109.4(3) . . ? C4 C3 N2 107.2(3) . . ? C3 C4 N1 107.2(3) . . ? N1 C1 C5 110.7(2) . . ? C6 C5 C1 113.4(3) . . ? C6 C5 C12 111.5(2) . . ? C1 C5 C12 111.3(2) . . ? C7 C6 C11 117.8(3) . . ? C7 C6 C5 123.0(3) . . ? C11 C6 C5 119.2(3) . . ? C6 C7 C8 121.2(3) . . ? C9 C8 C7 119.4(3) . . ? C10 C9 C8 120.0(3) . . ? C11 C10 C9 120.3(3) . . ? C10 C11 C6 121.3(3) . . ? C13 C12 C17 118.5(3) . . ? C13 C12 C5 118.9(3) . . ? C17 C12 C5 122.5(3) . . ? C12 C13 C14 120.7(4) . . ? C15 C14 C13 119.4(5) . . ? C16 C15 C14 121.0(5) . . ? C15 C16 C17 119.9(5) . . ? C12 C17 C16 120.4(4) . . ? F3 C18 F2 108.6(7) . . ? F3 C18 F1 107.2(7) . . ? F2 C18 F1 108.0(7) . . ? F3 C18 S1 112.3(6) . . ? F2 C18 S1 111.4(6) . . ? F1 C18 S1 109.1(5) . . ? C2 N1 C4 108.3(3) . . ? C2 N1 C1 125.8(3) . . ? C4 N1 C1 125.8(3) . . ? C2 N2 C3 107.9(3) . . ? C2 N2 C20 126.3(3) . . ? C3 N2 C20 125.7(3) . . ? S1 N3 S2A 124.5(2) . . ? S1 N3 O21B 144.6(16) . . ? S2A N3 O21B 66.3(11) . . ? S1 N3 S2B 110.0(3) . . ? S2A N3 S2B 57.1(3) . . ? O21B N3 S2B 43.1(10) . . ? O11 S1 O12 119.0(2) . . ? O11 S1 N3 120.9(2) . . ? O12 S1 N3 104.8(2) . . ? O11 S1 C18 104.7(3) . . ? O12 S1 C18 102.5(4) . . ? N3 S1 C18 102.1(3) . . ? O22A S2A O21A 120.5(3) . . ? O22A S2A N3 108.4(3) . . ? O21A S2A N3 115.0(2) . . ? O22A S2A C19A 104.0(3) . . ? O21A S2A C19A 103.2(4) . . ? N3 S2A C19A 103.6(4) . . ? F5A C19A F6A 109.8(9) . . ? F5A C19A F4A 111.5(10) . . ? F6A C19A F4A 106.4(10) . . ? F5A C19A S2A 111.8(6) . . ? F6A C19A S2A 109.3(7) . . ? F4A C19A S2A 107.9(8) . . ? O22B S2B O21B 112(2) . . ? O22B S2B C19B 114(3) . . ? O21B S2B C19B 106(3) . . ? O22B S2B N3 133.0(11) . . ? O21B S2B N3 66.9(15) . . ? C19B S2B N3 110(3) . . ? F6B C19B F4B 136(4) . . ? F6B C19B F5B 112(4) . . ? F4B C19B F5B 83(5) . . ? F6B C19B S2B 116(5) . . ? F4B C19B S2B 103(5) . . ? F5B C19B S2B 93(4) . . ? S2B O21B N3 70.0(12) . . ? _chemical_name_common (Ph2CHCH2Ph)((CF3SO2)2N) # Attachment 'checkcif_fig6b.txt' data_teste2 _database_code_depnum_ccdc_archive 'CCDC 607812' _audit_creation_date 2006-05-16T17:52:18-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; [PhCH2CH2CH2(N2C3H3)CH3][N(SO2CF3] ; _chemical_formula_moiety 'C15 H17 F6 N3 O4 S2' _chemical_formula_sum 'C15 H17 F6 N3 O4 S2' _chemical_formula_weight 481.44 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/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 11.1807(2) _cell_length_b 14.8585(3) _cell_length_c 12.8594(3) _cell_angle_alpha 90 _cell_angle_beta 105.4960(10) _cell_angle_gamma 90 _cell_volume 2058.65(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 145 _cell_measurement_theta_min 3 _cell_measurement_theta_max 27 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.16 _exptl_crystal_density_diffrn 1.553 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 984 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.339 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details SADABS _exptl_absorpt_correction_T_min 0.98282 _exptl_absorpt_correction_T_max 1 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi scan' _diffrn_reflns_av_R_equivalents 0.0439 _diffrn_reflns_av_unetI/netI 0.0342 _diffrn_reflns_number 36755 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 28.36 _diffrn_reflns_theta_full 28.36 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _reflns_number_total 5127 _reflns_number_gt 2659 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker APEX2/BIS/COSMO' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT/SADABS' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Crysal Impact Diamond 3' _computing_publication_material WinGX #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.1847P)^2^+1.4100P] 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_number_reflns 5127 _refine_ls_number_parameters 284 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1524 _refine_ls_R_factor_gt 0.0921 _refine_ls_wR_factor_ref 0.3457 _refine_ls_wR_factor_gt 0.2952 _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_restrained_S_all 1.072 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 1.007 _refine_diff_density_min -0.662 _refine_diff_density_rms 0.084 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C27 C 0.3474(6) 0.3174(4) 0.0932(6) 0.0929(18) Uani 1 1 d . . . C2 C 0.2534(4) 0.5395(3) 0.3817(4) 0.0591(11) Uani 1 1 d . . . H2 H 0.3134 0.5036 0.364 0.071 Uiso 1 1 calc R . . C4 C 0.0756(4) 0.5937(3) 0.3909(4) 0.0604(11) Uani 1 1 d . . . H4 H -0.0094 0.6013 0.38 0.072 Uiso 1 1 calc R . . C5 C 0.1659(4) 0.6448(3) 0.4529(4) 0.0600(11) Uani 1 1 d . . . H5 H 0.1549 0.6946 0.4932 0.072 Uiso 1 1 calc R . . C6 C 0.3983(5) 0.6466(5) 0.5017(5) 0.0939(18) Uani 1 1 d . . . H6A H 0.3885 0.6977 0.5444 0.141 Uiso 1 1 calc R . . H6B H 0.4408 0.6646 0.4494 0.141 Uiso 1 1 calc R . . H6C H 0.4458 0.6011 0.5478 0.141 Uiso 1 1 calc R . . C20 C 0.3326(6) 0.0285(4) 0.3031(6) 0.0888(16) Uani 1 1 d . . . N1 N 0.2762(3) 0.6106(2) 0.4464(3) 0.0589(9) Uani 1 1 d . . . O25 O 0.1779(4) 0.2421(4) 0.1613(6) 0.132(2) Uani 1 1 d . . . O26 O 0.3430(6) 0.3224(3) 0.2913(4) 0.1249(18) Uani 1 1 d . . . O19 O 0.2361(4) 0.0637(4) 0.1072(4) 0.1149(16) Uani 1 1 d . . . O18 O 0.4623(5) 0.0348(4) 0.1675(5) 0.134(2) Uani 1 1 d . . . F23 F 0.2368(4) 0.0610(4) 0.3309(4) 0.1362(17) Uani 1 1 d . . . F22 F 0.4307(5) 0.0408(4) 0.3843(4) 0.1377(16) Uani 1 1 d . . . F21 F 0.3155(4) -0.0584(3) 0.2877(5) 0.150(2) Uani 1 1 d . . . C10 C -0.0994(4) 0.2387(3) 0.3184(4) 0.0560(10) Uani 1 1 d . . . C15 C -0.0204(5) 0.1873(3) 0.3961(4) 0.0716(13) Uani 1 1 d . . . H15 H 0.0647 0.1971 0.4115 0.086 Uiso 1 1 calc R . . C14 C -0.0645(7) 0.1224(4) 0.4508(5) 0.0942(19) Uani 1 1 d . . . H14 H -0.0091 0.088 0.5025 0.113 Uiso 1 1 calc R . . C13 C -0.1876(9) 0.1071(4) 0.4312(6) 0.104(2) Uani 1 1 d . . . H13 H -0.2168 0.0631 0.4696 0.125 Uiso 1 1 calc R . . C12 C -0.2690(6) 0.1569(5) 0.3544(6) 0.0894(18) Uani 1 1 d . . . H12 H -0.3539 0.1462 0.3399 0.107 Uiso 1 1 calc R . . C11 C -0.2253(4) 0.2229(3) 0.2984(4) 0.0662(12) Uani 1 1 d . . . H11 H -0.281 0.257 0.2468 0.079 Uiso 1 1 calc R . . C9 C -0.0497(5) 0.3116(3) 0.2606(4) 0.0665(12) Uani 1 1 d . . . H9B H -0.1175 0.3369 0.2048 0.08 Uiso 1 1 calc R . . H9A H 0.009 0.2854 0.2257 0.08 Uiso 1 1 calc R . . C8 C 0.0142(4) 0.3867(3) 0.3352(4) 0.0596(10) Uani 1 1 d . . . H8B H -0.0457 0.4162 0.3661 0.071 Uiso 1 1 calc R . . H8A H 0.0786 0.3613 0.3939 0.071 Uiso 1 1 calc R . . C7 C 0.0709(4) 0.4552(3) 0.2757(4) 0.0622(11) Uani 1 1 d . . . H7A H 0.1302 0.4254 0.2443 0.075 Uiso 1 1 calc R . . H7B H 0.0062 0.4807 0.2172 0.075 Uiso 1 1 calc R . . N3 N 0.1335(3) 0.5276(2) 0.3466(3) 0.0524(8) Uani 1 1 d . . . N16 N 0.3960(5) 0.1754(3) 0.2190(5) 0.1006(17) Uani 1 1 d . . . S17 S 0.35289(15) 0.07850(10) 0.18126(13) 0.0844(5) Uani 1 1 d . A . S24 S 0.31373(17) 0.26055(10) 0.20588(14) 0.0913(6) Uani 1 1 d . A . F28A F 0.2845(7) 0.3911(4) 0.0702(5) 0.133(3) Uani 0.860(12) 1 d P A 1 F30B F 0.3315(9) 0.2699(5) 0.0070(6) 0.119(2) Uani 0.860(12) 1 d P A 1 F30A F 0.4686(5) 0.3336(4) 0.1156(6) 0.138(3) Uani 0.860(12) 1 d P A 1 F28B F 0.390(4) 0.406(2) 0.110(3) 0.114(12) Uiso 0.140(12) 1 d P A 2 F29B F 0.205(3) 0.353(2) 0.077(2) 0.097(10) Uiso 0.140(12) 1 d P A 2 F29A F 0.287(3) 0.258(2) 0.012(3) 0.072(9) Uiso 0.140(12) 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 C27 0.102(5) 0.072(4) 0.099(5) 0.008(3) 0.017(4) 0.009(3) C2 0.068(3) 0.055(2) 0.063(2) 0.005(2) 0.032(2) 0.005(2) C4 0.068(3) 0.053(2) 0.069(3) -0.004(2) 0.035(2) 0.007(2) C5 0.082(3) 0.047(2) 0.060(2) -0.0043(19) 0.035(2) -0.002(2) C6 0.075(3) 0.106(5) 0.102(4) -0.017(4) 0.025(3) -0.023(3) C20 0.087(4) 0.070(4) 0.103(4) 0.005(3) 0.014(3) -0.004(3) N1 0.068(2) 0.056(2) 0.057(2) 0.0007(17) 0.0247(17) -0.0077(17) O25 0.061(3) 0.130(4) 0.212(6) 0.008(4) 0.048(3) 0.017(2) O26 0.188(5) 0.091(3) 0.082(3) -0.016(2) 0.013(3) 0.003(3) O19 0.112(3) 0.123(4) 0.100(3) -0.020(3) 0.011(3) 0.018(3) O18 0.111(3) 0.131(4) 0.190(6) -0.023(4) 0.094(4) 0.007(3) F23 0.112(3) 0.183(5) 0.133(3) 0.007(3) 0.066(3) 0.012(3) F22 0.137(3) 0.148(4) 0.113(3) 0.022(3) 0.007(3) -0.004(3) F21 0.156(4) 0.067(2) 0.219(6) 0.024(3) 0.037(4) -0.024(2) C10 0.067(3) 0.047(2) 0.055(2) -0.0121(18) 0.0186(19) -0.0047(18) C15 0.075(3) 0.057(3) 0.081(3) 0.000(2) 0.018(2) 0.007(2) C14 0.142(6) 0.054(3) 0.082(4) 0.002(3) 0.022(4) 0.002(3) C13 0.175(7) 0.062(3) 0.089(4) -0.017(3) 0.059(5) -0.049(4) C12 0.090(4) 0.088(4) 0.099(4) -0.038(4) 0.040(3) -0.044(3) C11 0.064(3) 0.062(3) 0.069(3) -0.018(2) 0.013(2) -0.008(2) C9 0.082(3) 0.061(3) 0.060(3) -0.010(2) 0.026(2) -0.010(2) C8 0.076(3) 0.051(2) 0.056(2) -0.0021(18) 0.024(2) -0.0076(19) C7 0.080(3) 0.056(2) 0.059(2) -0.009(2) 0.033(2) -0.010(2) N3 0.067(2) 0.0451(18) 0.0539(18) -0.0026(14) 0.0310(16) -0.0019(15) N16 0.083(3) 0.070(3) 0.136(5) 0.012(3) 0.006(3) 0.001(2) S17 0.1015(11) 0.0682(9) 0.0862(10) -0.0124(7) 0.0296(8) -0.0121(7) S24 0.1223(13) 0.0679(9) 0.0935(11) 0.0071(7) 0.0460(9) 0.0239(8) F28A 0.173(8) 0.089(3) 0.144(4) 0.042(3) 0.053(4) 0.059(4) F30B 0.144(6) 0.130(5) 0.099(4) 0.002(3) 0.058(4) 0.009(4) F30A 0.096(4) 0.117(4) 0.212(6) 0.027(4) 0.057(4) -0.018(3) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C27 F30B 1.286(9) . ? C27 F28A 1.292(7) . ? C27 F30A 1.331(8) . ? C27 F29A 1.40(4) . ? C27 F28B 1.40(3) . ? C27 F29B 1.63(3) . ? C27 S24 1.801(7) . ? C2 N3 1.308(5) . ? C2 N1 1.327(6) . ? C4 C5 1.342(6) . ? C4 N3 1.380(5) . ? C5 N1 1.357(6) . ? C6 N1 1.462(6) . ? C20 F23 1.308(7) . ? C20 F22 1.310(7) . ? C20 F21 1.313(7) . ? C20 S17 1.803(7) . ? O25 S24 1.499(5) . ? O26 S24 1.402(5) . ? O19 S17 1.413(5) . ? O18 S17 1.437(5) . ? C10 C15 1.375(7) . ? C10 C11 1.381(6) . ? C10 C9 1.502(6) . ? C15 C14 1.362(8) . ? C14 C13 1.351(10) . ? C13 C12 1.367(10) . ? C12 C11 1.381(8) . ? C9 C8 1.520(6) . ? C8 C7 1.512(6) . ? C7 N3 1.462(5) . ? N16 S24 1.546(5) . ? N16 S17 1.555(5) . ? 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 F30B C27 F28A 109.0(7) . . ? F30B C27 F30A 100.6(7) . . ? F28A C27 F30A 110.9(6) . . ? F30B C27 F29A 23.0(13) . . ? F28A C27 F29A 103.8(15) . . ? F30A C27 F29A 122.3(15) . . ? F30B C27 F28B 127.9(16) . . ? F28A C27 F28B 51.6(15) . . ? F30A C27 F28B 60.8(16) . . ? F29A C27 F28B 142(2) . . ? F30B C27 F29B 99.3(11) . . ? F28A C27 F29B 41.2(11) . . ? F30A C27 F29B 150.5(13) . . ? F29A C27 F29B 81.3(17) . . ? F28B C27 F29B 90(2) . . ? F30B C27 S24 115.2(6) . . ? F28A C27 S24 111.3(5) . . ? F30A C27 S24 109.3(5) . . ? F29A C27 S24 98.3(14) . . ? F28B C27 S24 116.8(15) . . ? F29B C27 S24 81.2(12) . . ? N3 C2 N1 109.3(4) . . ? C5 C4 N3 106.7(4) . . ? C4 C5 N1 107.7(4) . . ? F23 C20 F22 107.7(6) . . ? F23 C20 F21 107.9(6) . . ? F22 C20 F21 108.3(6) . . ? F23 C20 S17 112.8(5) . . ? F22 C20 S17 111.2(4) . . ? F21 C20 S17 108.7(5) . . ? C2 N1 C5 108.1(4) . . ? C2 N1 C6 126.5(4) . . ? C5 N1 C6 125.4(4) . . ? C15 C10 C11 117.7(4) . . ? C15 C10 C9 120.6(4) . . ? C11 C10 C9 121.6(4) . . ? C14 C15 C10 121.2(5) . . ? C13 C14 C15 120.9(6) . . ? C14 C13 C12 119.6(6) . . ? C13 C12 C11 120.0(6) . . ? C10 C11 C12 120.6(5) . . ? C10 C9 C8 113.0(4) . . ? C7 C8 C9 111.4(4) . . ? N3 C7 C8 112.0(3) . . ? C2 N3 C4 108.2(4) . . ? C2 N3 C7 126.2(4) . . ? C4 N3 C7 125.6(4) . . ? S24 N16 S17 126.7(3) . . ? O19 S17 O18 120.7(3) . . ? O19 S17 N16 120.5(3) . . ? O18 S17 N16 104.7(3) . . ? O19 S17 C20 102.3(3) . . ? O18 S17 C20 103.3(3) . . ? N16 S17 C20 102.2(3) . . ? O26 S24 O25 114.8(4) . . ? O26 S24 N16 116.3(3) . . ? O25 S24 N16 113.9(3) . . ? O26 S24 C27 105.5(3) . . ? O25 S24 C27 100.7(3) . . ? N16 S24 C27 103.0(3) . . ? _chemical_name_common (PhCH2CH2CH2(N2C3H3)CH3)(N(SO2CF3) # Attachment 'checkcif_fig6c.txt' data_p21n _database_code_depnum_ccdc_archive 'CCDC 671958' _audit_creation_date 2007-12-26T12:25:28-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.2 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ESLJP05 ; _chemical_formula_moiety 'C14 H15 F6 N3 O4 S2' _chemical_formula_sum 'C14 H15 F6 N3 O4 S2' _chemical_formula_weight 467.41 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _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 9.7783(9) _cell_length_b 15.2038(16) _cell_length_c 12.8926(14) _cell_angle_alpha 90 _cell_angle_beta 92.951(6) _cell_angle_gamma 90 _cell_volume 1914.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 123 _cell_measurement_theta_min 2 _cell_measurement_theta_max 29 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.61 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.12 _exptl_crystal_density_diffrn 1.622 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 952 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.362 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details SADABS _exptl_absorpt_correction_T_min 0.80003 _exptl_absorpt_correction_T_max 1 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi scan' _diffrn_reflns_av_R_equivalents 0.0375 _diffrn_reflns_av_unetI/netI 0.0371 _diffrn_reflns_number 23008 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 30.58 _diffrn_reflns_theta_full 30.58 _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.995 _reflns_number_total 5848 _reflns_number_gt 4457 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker APEX2/BIS/COSMO' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT/SADABS' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Crysal Impact Diamond 3' _computing_publication_material WinGX #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0538P)^2^+0.9831P] 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_number_reflns 5848 _refine_ls_number_parameters 262 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0596 _refine_ls_R_factor_gt 0.0432 _refine_ls_wR_factor_ref 0.1233 _refine_ls_wR_factor_gt 0.1127 _refine_ls_goodness_of_fit_ref 1.085 _refine_ls_restrained_S_all 1.085 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.592 _refine_diff_density_min -0.524 _refine_diff_density_rms 0.07 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.19567(4) 0.19669(3) 0.61378(3) 0.02027(11) Uani 1 1 d . . . S2 S 0.20672(4) 0.37499(3) 0.67145(3) 0.01953(11) Uani 1 1 d . . . C8 C 0.48706(17) 0.34427(12) 0.39723(14) 0.0205(3) Uani 1 1 d . . . H8A H 0.4202 0.3017 0.423 0.025 Uiso 1 1 calc R . . H8B H 0.5145 0.3239 0.3284 0.025 Uiso 1 1 calc R . . C11 C 0.61578(17) 0.31464(12) 0.56549(14) 0.0213(3) Uani 1 1 d . . . H11 H 0.5461 0.2822 0.5971 0.026 Uiso 1 1 calc R . . C6 C 0.29960(17) 0.43244(11) 0.30800(14) 0.0206(3) Uani 1 1 d . . . C7 C 0.41978(18) 0.43496(12) 0.38604(14) 0.0227(3) Uani 1 1 d . . . H7A H 0.3884 0.4542 0.4542 0.027 Uiso 1 1 calc R . . H7B H 0.4879 0.4782 0.3634 0.027 Uiso 1 1 calc R . . C10 C 0.81037(17) 0.38244(12) 0.53907(14) 0.0215(3) Uani 1 1 d . . . H10 H 0.9003 0.4054 0.5503 0.026 Uiso 1 1 calc R . . C5 C 0.31527(19) 0.45553(13) 0.20525(15) 0.0277(4) Uani 1 1 d . . . H5 H 0.4019 0.4752 0.1845 0.033 Uiso 1 1 calc R . . C9 C 0.72948(17) 0.39005(11) 0.45163(14) 0.0203(3) Uani 1 1 d . . . H9 H 0.7517 0.4191 0.3895 0.024 Uiso 1 1 calc R . . C12 C 0.7862(2) 0.31183(15) 0.71543(15) 0.0310(4) Uani 1 1 d . . . H12A H 0.8794 0.3344 0.7288 0.046 Uiso 1 1 calc R . . H12B H 0.7864 0.2477 0.7232 0.046 Uiso 1 1 calc R . . H12C H 0.7254 0.3379 0.765 0.046 Uiso 1 1 calc R . . C2 C 0.06183(19) 0.39793(14) 0.26403(18) 0.0316(4) Uani 1 1 d . . . H2 H -0.0249 0.378 0.2844 0.038 Uiso 1 1 calc R . . C1 C 0.17141(18) 0.40350(14) 0.33707(15) 0.0270(4) Uani 1 1 d . . . H1 H 0.159 0.3875 0.4072 0.032 Uiso 1 1 calc R . . C3 C 0.0791(2) 0.42126(14) 0.16219(17) 0.0327(4) Uani 1 1 d . . . H3 H 0.0043 0.4175 0.1124 0.039 Uiso 1 1 calc R . . C4 C 0.2060(2) 0.45024(15) 0.13236(16) 0.0350(5) Uani 1 1 d . . . H4 H 0.218 0.4664 0.0622 0.042 Uiso 1 1 calc R . . N1 N 0.60800(14) 0.34749(10) 0.46958(11) 0.0186(3) Uani 1 1 d . . . N2 N 0.73778(14) 0.33497(10) 0.60941(12) 0.0212(3) Uani 1 1 d . . . C13 C 0.0697(2) 0.16444(13) 0.51084(14) 0.0269(4) Uani 1 1 d . . . C14 C 0.2214(3) 0.36831(14) 0.81356(17) 0.0375(5) Uani 1 1 d . . . F1 F -0.05737(11) 0.17067(9) 0.54207(9) 0.0343(3) Uani 1 1 d . . . F6 F 0.28993(17) 0.29606(9) 0.84202(11) 0.0557(4) Uani 1 1 d . . . F3 F 0.07935(15) 0.21493(11) 0.42794(9) 0.0490(4) Uani 1 1 d . . . F2 F 0.09197(16) 0.08167(9) 0.48445(12) 0.0509(4) Uani 1 1 d . . . F5 F 0.28943(19) 0.43787(10) 0.85204(11) 0.0582(5) Uani 1 1 d . . . F4 F 0.09881(18) 0.36519(10) 0.85378(11) 0.0551(4) Uani 1 1 d . . . O3 O 0.34493(14) 0.38156(9) 0.64059(13) 0.0341(3) Uani 1 1 d . . . O2 O 0.32368(13) 0.20150(9) 0.56409(12) 0.0325(3) Uani 1 1 d . . . O1 O 0.18152(15) 0.13238(9) 0.69310(11) 0.0319(3) Uani 1 1 d . . . O4 O 0.11668(14) 0.44742(9) 0.65027(11) 0.0291(3) Uani 1 1 d . . . N3 N 0.12921(14) 0.28755(10) 0.64221(13) 0.0239(3) 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 S1 0.01755(19) 0.0202(2) 0.0232(2) -0.00096(16) 0.00161(15) 0.00106(15) S2 0.01680(19) 0.0189(2) 0.0229(2) 0.00105(16) 0.00043(15) -0.00142(14) C8 0.0169(7) 0.0220(8) 0.0223(8) -0.0026(7) -0.0018(6) -0.0010(6) C11 0.0169(7) 0.0226(8) 0.0246(8) 0.0030(7) 0.0031(6) 0.0018(6) C6 0.0188(7) 0.0174(8) 0.0253(8) -0.0037(7) -0.0022(6) 0.0013(6) C7 0.0223(8) 0.0209(8) 0.0243(8) -0.0022(7) -0.0037(6) 0.0005(6) C10 0.0158(7) 0.0220(8) 0.0269(9) 0.0005(7) 0.0022(6) -0.0003(6) C5 0.0239(8) 0.0308(10) 0.0280(9) 0.0011(8) -0.0006(7) -0.0043(7) C9 0.0180(7) 0.0193(8) 0.0236(8) 0.0002(7) 0.0018(6) -0.0015(6) C12 0.0250(9) 0.0437(12) 0.0240(9) 0.0064(8) -0.0011(7) 0.0058(8) C2 0.0176(8) 0.0324(10) 0.0448(12) -0.0087(9) 0.0022(8) 0.0002(7) C1 0.0226(8) 0.0307(10) 0.0281(9) -0.0038(8) 0.0040(7) -0.0020(7) C3 0.0251(9) 0.0314(10) 0.0402(11) -0.0067(9) -0.0117(8) 0.0040(8) C4 0.0370(11) 0.0406(12) 0.0263(10) 0.0034(9) -0.0077(8) -0.0030(9) N1 0.0155(6) 0.0178(7) 0.0224(7) 0.0000(6) 0.0007(5) 0.0008(5) N2 0.0166(6) 0.0243(8) 0.0228(7) 0.0022(6) 0.0011(5) 0.0030(5) C13 0.0307(9) 0.0276(10) 0.0222(9) -0.0038(7) 0.0009(7) -0.0032(7) C14 0.0568(14) 0.0257(10) 0.0286(10) 0.0003(8) -0.0101(9) -0.0122(9) F1 0.0232(5) 0.0429(7) 0.0364(7) -0.0038(5) -0.0032(5) -0.0085(5) F6 0.0778(11) 0.0384(8) 0.0470(8) 0.0138(7) -0.0340(8) -0.0090(7) F3 0.0577(9) 0.0673(10) 0.0214(6) 0.0116(6) -0.0031(6) -0.0136(7) F2 0.0583(9) 0.0372(8) 0.0563(9) -0.0266(7) -0.0070(7) 0.0017(7) F5 0.0946(13) 0.0377(8) 0.0398(8) -0.0053(6) -0.0205(8) -0.0274(8) F4 0.0799(11) 0.0538(9) 0.0339(8) -0.0038(7) 0.0249(7) -0.0152(8) O3 0.0215(6) 0.0280(7) 0.0536(9) -0.0002(7) 0.0100(6) -0.0055(5) O2 0.0195(6) 0.0288(7) 0.0501(9) -0.0040(6) 0.0118(6) 0.0030(5) O1 0.0378(8) 0.0291(7) 0.0286(7) 0.0073(6) -0.0012(6) 0.0033(6) O4 0.0280(7) 0.0224(7) 0.0365(8) 0.0010(6) -0.0019(6) 0.0043(5) N3 0.0162(6) 0.0211(7) 0.0345(8) -0.0077(6) 0.0016(6) -0.0003(5) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 1.4267(14) . ? S1 O2 1.4371(13) . ? S1 N3 1.5778(15) . ? S1 C13 1.831(2) . ? S2 O4 1.4276(14) . ? S2 O3 1.4319(13) . ? S2 N3 1.5666(16) . ? S2 C14 1.833(2) . ? C8 N1 1.469(2) . ? C8 C7 1.531(2) . ? C11 N2 1.330(2) . ? C11 N1 1.332(2) . ? C6 C5 1.387(3) . ? C6 C1 1.398(2) . ? C6 C7 1.508(2) . ? C10 C9 1.348(3) . ? C10 N2 1.383(2) . ? C5 C4 1.388(3) . ? C9 N1 1.383(2) . ? C12 N2 1.466(2) . ? C2 C3 1.379(3) . ? C2 C1 1.392(3) . ? C3 C4 1.389(3) . ? C13 F3 1.323(2) . ? C13 F2 1.325(2) . ? C13 F1 1.329(2) . ? C14 F6 1.329(3) . ? C14 F4 1.331(3) . ? C14 F5 1.332(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 118.24(9) . . ? O1 S1 N3 112.16(9) . . ? O2 S1 N3 115.95(8) . . ? O1 S1 C13 104.45(9) . . ? O2 S1 C13 105.04(9) . . ? N3 S1 C13 97.65(9) . . ? O4 S2 O3 118.34(9) . . ? O4 S2 N3 108.82(8) . . ? O3 S2 N3 116.37(8) . . ? O4 S2 C14 104.45(10) . . ? O3 S2 C14 104.79(11) . . ? N3 S2 C14 101.86(9) . . ? N1 C8 C7 110.96(14) . . ? N2 C11 N1 108.36(15) . . ? C5 C6 C1 118.73(17) . . ? C5 C6 C7 120.69(16) . . ? C1 C6 C7 120.53(16) . . ? C6 C7 C8 110.87(14) . . ? C9 C10 N2 107.11(15) . . ? C6 C5 C4 120.86(18) . . ? C10 C9 N1 106.97(15) . . ? C3 C2 C1 120.05(18) . . ? C2 C1 C6 120.49(18) . . ? C2 C3 C4 120.00(19) . . ? C5 C4 C3 119.87(19) . . ? C11 N1 C9 108.81(14) . . ? C11 N1 C8 125.63(14) . . ? C9 N1 C8 125.44(15) . . ? C11 N2 C10 108.75(15) . . ? C11 N2 C12 125.50(15) . . ? C10 N2 C12 125.75(15) . . ? F3 C13 F2 108.92(16) . . ? F3 C13 F1 108.07(17) . . ? F2 C13 F1 108.32(16) . . ? F3 C13 S1 110.91(14) . . ? F2 C13 S1 109.10(14) . . ? F1 C13 S1 111.46(12) . . ? F6 C14 F4 108.33(19) . . ? F6 C14 F5 108.56(19) . . ? F4 C14 F5 109.0(2) . . ? F6 C14 S2 109.51(16) . . ? F4 C14 S2 111.45(16) . . ? F5 C14 S2 109.89(15) . . ? S2 N3 S1 126.79(9) . . ? _chemical_name_common ESLJP05