Electronic Supplementary Material for CrystEngComm This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full CrystEngComm #=============================================================================== # 2. PROCESSING SUMMARY (JOURNAL OFFICE ONLY) _journal_coden_Cambridge 1350 #============================================================================== #=============================================================================== # 1. SUBMISSION DETAILS _publ_contact_author_name 'Neil Winterton' _publ_contact_author_address ; Liverpool Centre for Materials and Catalysis, Department of Chemistry, University of Liverpool, Liverpool. L69 7ZD ; _publ_contact_author_email n.winterton@liv.ac.uk _publ_contact_author_fax +441517943583 _publ_contact_author_phone +441517943585 # Publication choise FI, CI or EI for Inorganic # FM, CM or EM for Metal-organic # FO, CO or EO for Organic _publ_requested_category ? _publ_requested_coeditor_name ? _publ_contact_letter # Include date of submission ; Date of submission ? Please consider this CIF submission for publication as a Regular Structural Paper in CRYSTENGCOMM. ; _journal_year ? _journal_volume ? _journal_issue ? _journal_page_first ? _journal_page_last ? #=============================================================================== # 3. TITLE AND AUTHOR LIST _publ_section_title ; In situ crystallization of ionic liquids with melting points <-25 \%C ; _publ_section_title_footnote ; ? ; # The loop structure below should contain the names and adresses of all # authors, in the required order of publication. Repeat as necessary. loop_ _publ_author_name #_publ_author_footnote _publ_author_address A.R.Choudhury ; Liverpool Centre for Materials and Catalysis, Department of Chemistry, University of Liverpool, Liverpool. L69 7ZD ; N.Winterton ; Liverpool Centre for Materials and Catalysis, Department of Chemistry, University of Liverpool, Liverpool. L69 7ZD ; A.Steiner ; Liverpool Centre for Materials and Catalysis, Department of Chemistry, University of Liverpool, Liverpool. L69 7ZD ; A.I.Cooper ; Liverpool Centre for Materials and Catalysis, Department of Chemistry, University of Liverpool, Liverpool. L69 7ZD ; K.A.Johnson ; Liverpool Centre for Materials and Catalysis, Department of Chemistry, University of Liverpool, Liverpool. L69 7ZD ; #=============================================================================== # 4. TEXT _publ_section_synopsis ; ? ; _publ_section_abstract ; ? ; # Insert blank lines between paragraphs _publ_section_comment ; ? ; _publ_section_exptl_prep ; ? ; _publ_section_exptl_refinement ; ? ; # Insert blank lines between references _publ_section_references ; ? ; _publ_section_acknowledgements ; ? ; _publ_section_figure_captions ; View of the title compound with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 50% probability level. ; #=============================================================================== data_[emim]NTf2 _database_code_depnum_ccdc_archive 'CCDC 614037' # 0. AUDIT DETAILS _audit_creation_date 'Aug 04 13:39:26 2006' _audit_creation_method 'PLATON option' _audit_update_record ; ? ; #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; 1-ethyl-3-methylimidazolium bis(trifluoromethanesulfonlyl)imide ; _chemical_name_common ;1-ethyl-3-methylimidazolium bis(trifluoromethanesulfonlyl)imide ; _chemical_melting_point 247.3 _chemical_formula_moiety 'C6 H11 N2, C2 F6 N O4 S2' # Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)' _chemical_formula_structural ? _chemical_formula_sum 'C8 H11 F6 N3 O4 S2' _chemical_formula_iupac ? _chemical_formula_weight 391.34 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source S S 0.1246 0.1234 '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' 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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_Hall 'P 2c -2ac' _symmetry_space_group_name_H-M 'P c a 21' _symmetry_Int_Tables_number 29 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,-y,1/2+z 3 1/2-x,y,1/2+z 4 1/2+x,-y,z _cell_length_a 18.499(9) _cell_length_b 8.626(8) _cell_length_c 19.255(9) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 3073(4) _cell_formula_units_Z 8 _cell_measurement_temperature 230 _cell_measurement_reflns_used 755 _cell_measurement_theta_min 2.61 _cell_measurement_theta_max 18.14 _cell_special_details ; ? ; _exptl_crystal_description Rod _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.3 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.692 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 1584 _exptl_absorpt_coefficient_mu 0.432 _exptl_crystal_density_meas_temp ? # Permitted for _exptl_absorpt_correction_type : # analytical 'analytical from crystal shape' # Example: de Meulenaer&Tompa: ABST # cylinder 'cylindrical' # gaussian 'Gaussian from crystal shape' # Example: PLATON/ABSG # integration 'integration from crystal shape' # multi-scan 'symmetry-related measurements' # Example: SADABS, MULABS # none 'no absorption corr. applied' # numerical 'numerical from crystal shape' # psi-scan 'psi-scan corrections' # Example: PLATON/ABSP # refdelf 'refined from delta-F' # Example: SHELXA, DIFABS, DELABS # sphere 'spherical' # Example: PLATON/ABSS _exptl_absorpt_correction_type None # Example: '(North, Phillips & Mathews, 1968)' _exptl_absorpt_process_details ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ? ; _diffrn_ambient_temperature 230.0(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 'Bruker SMART CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? # number of measured reflections (redundant set) _diffrn_reflns_number 25029 _diffrn_reflns_av_R_equivalents 0.1722 _diffrn_reflns_av_sigmaI/netI 0.1271 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 25.35 _reflns_number_total 2947 _reflns_number_gt 1439 _reflns_threshold_expression >2sigma(I) _diffrn_measured_fraction_theta_max 0.768 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.768 _computing_data_collection 'Bruker SMART V5.628, (Bruker, 2004)' _computing_cell_refinement 'Bruker SMART V5.628, (Bruker, 2004)' _computing_data_reduction 'Bruker SAINT V6.45a, (Bruker, 2004)' _computing_structure_solution 'SIR92 (Altomare, 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; Ortep-32 for Windows (Farrugia, 1997), POV-Ray^TM^ for Windows Version 3.6 (The POV-Ray Team, 2004) and CAMERON (Watkin et. al., 1993) ; _computing_publication_material 'PLATON (Spek, 1990)' #=============================================================================== # 8. REFINEMENT DATA _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^)+(0.1293P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.5(3) _refine_ls_number_reflns 2947 _refine_ls_number_parameters 413 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1465 _refine_ls_R_factor_gt 0.0823 _refine_ls_wR_factor_ref 0.2225 _refine_ls_wR_factor_gt 0.1936 _refine_ls_goodness_of_fit_ref 0.948 _refine_ls_restrained_S_all 0.948 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.411 _refine_diff_density_min -0.352 _refine_diff_density_rms 0.105 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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 0.7828(3) -0.0827(4) -0.2483(2) 0.0452(14) Uani 1 1 d . . . S2 S 0.7275(4) 0.2157(5) -0.2720(3) 0.0527(17) Uani 1 1 d . . . F1 F 0.7987(15) -0.0187(16) -0.1165(6) 0.165(11) Uani 1 1 d . . . F2 F 0.7182(10) -0.1824(18) -0.1366(7) 0.113(6) Uani 1 1 d . . . F3 F 0.8278(9) -0.2473(14) -0.1451(7) 0.102(5) Uani 1 1 d . . . F4 F 0.7040(10) 0.2728(14) -0.1425(7) 0.108(5) Uani 1 1 d . . . F5 F 0.8131(10) 0.2953(15) -0.1733(7) 0.088(5) Uani 1 1 d . . . F6 F 0.7385(9) 0.4649(13) -0.2007(9) 0.121(6) Uani 1 1 d . . . O1 O 0.7620(9) -0.2211(12) -0.2818(7) 0.061(4) Uani 1 1 d . . . O2 O 0.8521(11) -0.0235(14) -0.2615(7) 0.069(5) Uani 1 1 d . . . O3 O 0.7866(9) 0.2531(12) -0.3159(7) 0.068(4) Uani 1 1 d . . . O4 O 0.6578(9) 0.2691(12) -0.2903(8) 0.077(4) Uani 1 1 d . . . N1 N 0.7301(11) -0.2964(16) -0.4390(6) 0.052(4) Uani 1 1 d . . . N3 N 0.7822(12) -0.0759(15) -0.4448(7) 0.055(5) Uani 1 1 d . . . N11 N 1.0213(9) 0.1967(13) -0.2839(7) 0.046(3) Uani 1 1 d . . . C2 C 0.7932(11) -0.2285(16) -0.4423(8) 0.041(5) Uani 1 1 d . . . H2 H 0.8379 -0.2780 -0.4429 0.050 Uiso 1 1 calc R . . C4 C 0.7069(13) -0.054(2) -0.4445(8) 0.050(5) Uani 1 1 d . . . H4 H 0.6827 0.0410 -0.4448 0.060 Uiso 1 1 calc R . . C5 C 0.6773(13) -0.191(3) -0.4435(9) 0.066(6) Uani 1 1 d . . . H5 H 0.6280 -0.2120 -0.4456 0.079 Uiso 1 1 calc R . . C6 C 0.7218(13) -0.467(2) -0.4350(11) 0.060(6) Uani 1 1 d . . . H6A H 0.6766 -0.4923 -0.4120 0.073 Uiso 1 1 calc R . . H6B H 0.7609 -0.5105 -0.4075 0.073 Uiso 1 1 calc R . . C7 C 0.7227(14) -0.543(2) -0.5101(11) 0.080(8) Uani 1 1 d . . . H7A H 0.6879 -0.4921 -0.5391 0.120 Uiso 1 1 calc R . . H7B H 0.7107 -0.6514 -0.5066 0.120 Uiso 1 1 calc R . . H7C H 0.7699 -0.5326 -0.5301 0.120 Uiso 1 1 calc R . . C8 C 0.8378(12) 0.039(2) -0.4574(13) 0.084(8) Uani 1 1 d . . . H8A H 0.8845 -0.0088 -0.4553 0.126 Uiso 1 1 calc R . . H8B H 0.8348 0.1191 -0.4227 0.126 Uiso 1 1 calc R . . H8C H 0.8309 0.0844 -0.5025 0.126 Uiso 1 1 calc R . . C9 C 0.7835(15) -0.132(3) -0.1615(11) 0.091(9) Uani 1 1 d . . . C10 C 0.7474(17) 0.315(2) -0.1902(11) 0.078(8) Uani 1 1 d . . . S3 S 0.9734(3) 0.2814(5) 0.0379(3) 0.0540(17) Uani 1 1 d . . . S4 S 1.0279(3) 0.5830(4) 0.0237(2) 0.0479(15) Uani 1 1 d . . . F7 F 0.9870(10) 0.0382(13) -0.0419(8) 0.120(6) Uani 1 1 d . . . F8 F 1.0588(11) 0.2202(15) -0.0659(7) 0.109(6) Uani 1 1 d . . . F9 F 0.9523(9) 0.2462(13) -0.0979(7) 0.103(5) Uani 1 1 d . . . F10 F 1.0498(10) 0.5331(15) -0.1076(6) 0.107(6) Uani 1 1 d . . . F11 F 0.9643(10) 0.6955(18) -0.0886(7) 0.113(5) Uani 1 1 d . . . F12 F 1.0711(8) 0.7627(12) -0.0750(6) 0.085(4) Uani 1 1 d . . . O5 O 1.0320(8) 0.2370(12) 0.0806(7) 0.058(4) Uani 1 1 d . . . O6 O 0.9045(8) 0.2235(12) 0.0548(8) 0.078(5) Uani 1 1 d . . . O7 O 1.1003(9) 0.5307(15) 0.0367(10) 0.081(5) Uani 1 1 d . . . O8 O 1.0031(9) 0.7204(14) 0.0588(7) 0.064(4) Uani 1 1 d . . . N13 N 0.9731(10) 0.4252(14) -0.2777(7) 0.046(3) Uani 1 1 d . . . N14 N 0.7204(9) 0.0393(18) -0.2545(8) 0.050(5) Uani 1 1 d . . . N15 N 0.9655(8) 0.4597(16) 0.0213(8) 0.044(4) Uani 1 1 d . . . C12 C 0.9618(12) 0.2714(19) -0.2856(8) 0.054(5) Uani 1 1 d . . . H12 H 0.9166 0.2260 -0.2914 0.065 Uiso 1 1 calc R . . C14 C 1.0457(14) 0.442(2) -0.2750(10) 0.069(6) Uani 1 1 d . . . H14 H 1.0705 0.5346 -0.2696 0.083 Uiso 1 1 calc R . . C15 C 1.0751(12) 0.3031(19) -0.2812(9) 0.062(6) Uani 1 1 d . . . H15 H 1.1244 0.2821 -0.2833 0.074 Uiso 1 1 calc R . . C16 C 1.0305(14) 0.0279(18) -0.2875(14) 0.063(7) Uani 1 1 d . . . H16A H 0.9927 -0.0154 -0.3165 0.075 Uiso 1 1 calc R . . H16B H 1.0765 0.0048 -0.3093 0.075 Uiso 1 1 calc R . . C17 C 1.0281(12) -0.046(2) -0.2199(12) 0.071(7) Uani 1 1 d . . . H17A H 1.0752 -0.0428 -0.1991 0.107 Uiso 1 1 calc R . . H17B H 1.0130 -0.1518 -0.2251 0.107 Uiso 1 1 calc R . . H17C H 0.9943 0.0079 -0.1907 0.107 Uiso 1 1 calc R . . C18 C 0.9198(13) 0.543(2) -0.2783(10) 0.075(8) Uani 1 1 d . . . H18A H 0.9190 0.5943 -0.2341 0.113 Uiso 1 1 calc R . . H18B H 0.8733 0.4980 -0.2874 0.113 Uiso 1 1 calc R . . H18C H 0.9310 0.6172 -0.3140 0.113 Uiso 1 1 calc R . . C19 C 0.9908(14) 0.194(2) -0.0442(11) 0.063(6) Uani 1 1 d . . . C20 C 1.0249(14) 0.6405(18) -0.0678(10) 0.071(7) 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 0.054(5) 0.035(2) 0.047(2) 0.0016(17) 0.001(2) -0.005(2) S2 0.055(5) 0.035(2) 0.068(3) 0.003(2) -0.006(3) 0.000(3) F1 0.37(3) 0.100(9) 0.029(7) -0.008(6) -0.035(11) 0.037(13) F2 0.123(16) 0.133(12) 0.084(10) 0.061(9) 0.035(9) 0.016(10) F3 0.103(13) 0.102(10) 0.102(11) 0.017(7) -0.026(8) 0.035(8) F4 0.152(16) 0.085(8) 0.087(10) -0.033(7) 0.039(9) -0.014(9) F5 0.100(15) 0.081(8) 0.084(9) -0.011(6) -0.024(9) -0.011(8) F6 0.171(15) 0.041(5) 0.151(13) -0.040(8) -0.004(11) -0.006(8) O1 0.077(13) 0.040(6) 0.066(9) -0.012(6) -0.011(8) 0.006(7) O2 0.079(15) 0.048(7) 0.080(10) -0.006(6) 0.003(9) -0.027(8) O3 0.091(14) 0.041(6) 0.072(9) 0.015(6) 0.022(8) 0.005(6) O4 0.076(13) 0.045(6) 0.111(11) 0.010(7) -0.020(9) 0.006(7) N1 0.069(16) 0.060(8) 0.027(7) 0.003(6) 0.013(7) -0.006(9) N3 0.067(17) 0.057(9) 0.041(8) 0.001(6) 0.035(8) 0.016(9) N11 0.037(10) 0.037(5) 0.064(6) 0.006(5) -0.007(6) -0.008(5) C2 0.033(16) 0.034(8) 0.057(10) -0.012(7) 0.011(8) 0.009(9) C4 0.05(2) 0.056(11) 0.043(10) -0.004(8) 0.020(9) 0.003(11) C5 0.037(18) 0.104(16) 0.056(11) -0.011(10) -0.016(10) 0.031(14) C6 0.057(18) 0.061(9) 0.063(13) 0.017(10) -0.005(11) -0.009(11) C7 0.11(2) 0.063(11) 0.066(13) -0.028(11) 0.033(12) -0.038(13) C8 0.07(2) 0.047(9) 0.14(2) 0.018(12) -0.018(15) -0.001(12) C9 0.12(3) 0.101(15) 0.053(13) -0.050(12) -0.039(15) 0.061(17) C10 0.12(3) 0.053(12) 0.061(13) 0.029(9) 0.012(16) 0.022(13) S3 0.044(5) 0.039(2) 0.079(3) 0.004(2) -0.008(3) -0.003(2) S4 0.058(5) 0.037(2) 0.049(2) -0.0011(18) 0.004(3) -0.008(2) F7 0.180(18) 0.046(6) 0.133(13) -0.016(8) 0.000(10) -0.012(9) F8 0.164(19) 0.076(8) 0.088(9) -0.019(6) 0.036(11) 0.034(10) F9 0.122(14) 0.084(8) 0.101(10) -0.027(7) -0.047(9) 0.010(8) F10 0.181(17) 0.079(7) 0.060(8) -0.019(6) 0.048(9) -0.008(8) F11 0.111(15) 0.131(11) 0.098(10) 0.043(9) -0.053(10) -0.008(10) F12 0.117(13) 0.055(6) 0.082(8) 0.028(5) 0.036(8) 0.004(6) O5 0.039(12) 0.045(6) 0.088(10) 0.013(6) -0.010(8) -0.013(6) O6 0.028(11) 0.043(6) 0.164(14) -0.002(7) 0.025(9) -0.016(6) O7 0.032(13) 0.062(7) 0.147(15) 0.022(8) -0.043(11) -0.011(7) O8 0.079(13) 0.049(7) 0.063(9) -0.011(6) 0.015(7) 0.023(8) N13 0.037(10) 0.037(5) 0.064(6) 0.006(5) -0.007(6) -0.008(5) N14 0.043(14) 0.052(7) 0.056(9) -0.011(8) -0.001(8) 0.004(9) N15 0.035(13) 0.051(7) 0.046(8) 0.000(7) 0.007(7) 0.004(8) C12 0.051(17) 0.068(11) 0.045(10) -0.003(8) -0.011(9) 0.014(10) C14 0.09(2) 0.049(11) 0.072(12) -0.002(10) -0.001(12) -0.032(12) C15 0.069(19) 0.057(11) 0.059(11) -0.007(9) 0.005(11) -0.003(10) C16 0.045(18) 0.041(8) 0.101(18) -0.002(11) 0.019(12) 0.015(9) C17 0.055(19) 0.057(10) 0.101(17) 0.008(12) -0.032(12) -0.003(11) C18 0.09(2) 0.071(11) 0.069(12) 0.035(11) 0.064(13) 0.039(14) C19 0.05(2) 0.077(14) 0.064(13) -0.010(11) 0.003(13) -0.009(11) C20 0.13(2) 0.031(8) 0.055(12) -0.002(8) 0.011(12) 0.013(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O2 1.402(18) . ? S1 O1 1.411(12) . ? S1 N14 1.567(17) . ? S1 C9 1.72(2) . ? S2 O4 1.413(15) . ? S2 O3 1.420(14) . ? S2 N14 1.564(16) . ? S2 C10 1.83(2) . ? F1 C9 1.33(2) . ? F2 C9 1.37(3) . ? F3 C9 1.33(2) . ? F4 C10 1.27(3) . ? F5 C10 1.27(3) . ? F6 C10 1.32(2) . ? N1 C2 1.31(2) . ? N1 C5 1.34(2) . ? N1 C6 1.49(2) . ? N3 C2 1.333(19) . ? N3 C4 1.41(2) . ? N3 C8 1.45(3) . ? N11 C12 1.28(2) . ? N11 C15 1.36(2) . ? N11 C16 1.47(2) . ? C2 H2 0.9300 . ? C4 C5 1.31(3) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C6 C7 1.59(3) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? S3 O6 1.407(14) . ? S3 O5 1.413(14) . ? S3 N15 1.578(15) . ? S3 C19 1.78(2) . ? S4 O7 1.436(16) . ? S4 O8 1.440(12) . ? S4 N15 1.570(15) . ? S4 C20 1.830(19) . ? F7 C19 1.35(2) . ? F8 C19 1.34(2) . ? F9 C19 1.33(2) . ? F10 C20 1.288(19) . ? F11 C20 1.28(3) . ? F12 C20 1.36(2) . ? N13 C12 1.35(2) . ? N13 C14 1.35(2) . ? N13 C18 1.42(2) . ? C12 H12 0.9300 . ? C14 C15 1.32(3) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 C17 1.45(3) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? 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 O2 S1 O1 118.4(9) . . ? O2 S1 N14 114.5(9) . . ? O1 S1 N14 109.4(9) . . ? O2 S1 C9 105.0(12) . . ? O1 S1 C9 103.8(10) . . ? N14 S1 C9 104.1(9) . . ? O4 S2 O3 118.7(9) . . ? O4 S2 N14 107.1(9) . . ? O3 S2 N14 114.5(8) . . ? O4 S2 C10 104.2(11) . . ? O3 S2 C10 104.5(11) . . ? N14 S2 C10 106.6(8) . . ? C2 N1 C5 110.2(17) . . ? C2 N1 C6 122.6(17) . . ? C5 N1 C6 127(2) . . ? C2 N3 C4 106.6(17) . . ? C2 N3 C8 125(2) . . ? C4 N3 C8 127.5(16) . . ? C12 N11 C15 107.0(16) . . ? C12 N11 C16 126.8(17) . . ? C15 N11 C16 126.1(17) . . ? N1 C2 N3 107.9(17) . . ? N1 C2 H2 126.0 . . ? N3 C2 H2 126.0 . . ? C5 C4 N3 106.9(19) . . ? C5 C4 H4 126.5 . . ? N3 C4 H4 126.5 . . ? C4 C5 N1 108(2) . . ? C4 C5 H5 125.9 . . ? N1 C5 H5 125.9 . . ? N1 C6 C7 111.1(15) . . ? N1 C6 H6A 109.4 . . ? C7 C6 H6A 109.4 . . ? N1 C6 H6B 109.4 . . ? C7 C6 H6B 109.4 . . ? H6A C6 H6B 108.0 . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N3 C8 H8A 109.5 . . ? N3 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N3 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? F3 C9 F1 105.2(17) . . ? F3 C9 F2 103(2) . . ? F1 C9 F2 101(2) . . ? F3 C9 S1 114.8(16) . . ? F1 C9 S1 117(2) . . ? F2 C9 S1 114.3(15) . . ? F5 C10 F4 112(2) . . ? F5 C10 F6 107(2) . . ? F4 C10 F6 108(2) . . ? F5 C10 S2 110.5(16) . . ? F4 C10 S2 111(2) . . ? F6 C10 S2 107.5(14) . . ? O6 S3 O5 117.7(9) . . ? O6 S3 N15 108.0(8) . . ? O5 S3 N15 116.9(8) . . ? O6 S3 C19 102.6(10) . . ? O5 S3 C19 105.2(11) . . ? N15 S3 C19 104.4(9) . . ? O7 S4 O8 118.3(10) . . ? O7 S4 N15 118.6(8) . . ? O8 S4 N15 109.7(10) . . ? O7 S4 C20 106.3(11) . . ? O8 S4 C20 102.7(8) . . ? N15 S4 C20 97.7(9) . . ? C12 N13 C14 105.1(15) . . ? C12 N13 C18 127(2) . . ? C14 N13 C18 128.1(18) . . ? S2 N14 S1 127.5(12) . . ? S4 N15 S3 125.9(11) . . ? N11 C12 N13 111.1(18) . . ? N11 C12 H12 124.4 . . ? N13 C12 H12 124.4 . . ? C15 C14 N13 108.2(17) . . ? C15 C14 H14 125.9 . . ? N13 C14 H14 125.9 . . ? C14 C15 N11 108(2) . . ? C14 C15 H15 125.9 . . ? N11 C15 H15 125.9 . . ? C17 C16 N11 112.9(19) . . ? C17 C16 H16A 109.0 . . ? N11 C16 H16A 109.0 . . ? C17 C16 H16B 109.0 . . ? N11 C16 H16B 109.0 . . ? H16A C16 H16B 107.8 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N13 C18 H18A 109.5 . . ? N13 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? N13 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? F9 C19 F8 101.7(19) . . ? F9 C19 F7 109.7(18) . . ? F8 C19 F7 103.1(19) . . ? F9 C19 S3 116.6(17) . . ? F8 C19 S3 111.9(15) . . ? F7 C19 S3 112.5(15) . . ? F11 C20 F10 113(2) . . ? F11 C20 F12 103.3(15) . . ? F10 C20 F12 105.8(18) . . ? F11 C20 S4 115.3(16) . . ? F10 C20 S4 111.6(13) . . ? F12 C20 S4 106.8(14) . . ? 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 C5 N1 C2 N3 3.8(17) . . . . ? C6 N1 C2 N3 -179.4(15) . . . . ? C4 N3 C2 N1 -1.4(17) . . . . ? C8 N3 C2 N1 -171.9(16) . . . . ? C2 N3 C4 C5 -1.4(18) . . . . ? C8 N3 C4 C5 168.7(18) . . . . ? N3 C4 C5 N1 3.6(18) . . . . ? C2 N1 C5 C4 -4.7(18) . . . . ? C6 N1 C5 C4 178.6(16) . . . . ? C2 N1 C6 C7 -85(2) . . . . ? C5 N1 C6 C7 91(2) . . . . ? O2 S1 C9 F3 -66(2) . . . . ? O1 S1 C9 F3 59(2) . . . . ? N14 S1 C9 F3 173.3(19) . . . . ? O2 S1 C9 F1 58(2) . . . . ? O1 S1 C9 F1 -177(2) . . . . ? N14 S1 C9 F1 -63(2) . . . . ? O2 S1 C9 F2 175.5(15) . . . . ? O1 S1 C9 F2 -59.6(17) . . . . ? N14 S1 C9 F2 54.9(17) . . . . ? O4 S2 C10 F5 -170.0(14) . . . . ? O3 S2 C10 F5 -44.7(16) . . . . ? N14 S2 C10 F5 76.9(17) . . . . ? O4 S2 C10 F4 64.3(17) . . . . ? O3 S2 C10 F4 -170.4(16) . . . . ? N14 S2 C10 F4 -49(2) . . . . ? O4 S2 C10 F6 -54(2) . . . . ? O3 S2 C10 F6 71(2) . . . . ? N14 S2 C10 F6 -167.0(19) . . . . ? O4 S2 N14 S1 164.4(12) . . . . ? O3 S2 N14 S1 30.6(15) . . . . ? C10 S2 N14 S1 -84.5(15) . . . . ? O2 S1 N14 S2 -1.1(15) . . . . ? O1 S1 N14 S2 -136.7(12) . . . . ? C9 S1 N14 S2 112.9(14) . . . . ? O7 S4 N15 S3 5.2(16) . . . . ? O8 S4 N15 S3 -135.0(12) . . . . ? C20 S4 N15 S3 118.5(13) . . . . ? O6 S3 N15 S4 158.9(12) . . . . ? O5 S3 N15 S4 23.4(16) . . . . ? C19 S3 N15 S4 -92.4(14) . . . . ? C15 N11 C12 N13 -5.6(19) . . . . ? C16 N11 C12 N13 177.0(18) . . . . ? C14 N13 C12 N11 3.4(19) . . . . ? C18 N13 C12 N11 178.7(15) . . . . ? C12 N13 C14 C15 0.2(19) . . . . ? C18 N13 C14 C15 -175.0(17) . . . . ? N13 C14 C15 N11 -3(2) . . . . ? C12 N11 C15 C14 6(2) . . . . ? C16 N11 C15 C14 -177.0(19) . . . . ? C12 N11 C16 C17 -89(2) . . . . ? C15 N11 C16 C17 94(2) . . . . ? O6 S3 C19 F9 71.1(17) . . . . ? O5 S3 C19 F9 -165.2(15) . . . . ? N15 S3 C19 F9 -42(2) . . . . ? O6 S3 C19 F8 -172.5(15) . . . . ? O5 S3 C19 F8 -48.8(17) . . . . ? N15 S3 C19 F8 74.9(17) . . . . ? O6 S3 C19 F7 -57(2) . . . . ? O5 S3 C19 F7 67(2) . . . . ? N15 S3 C19 F7 -169.5(17) . . . . ? O7 S4 C20 F11 -178.0(15) . . . . ? O8 S4 C20 F11 -53.1(18) . . . . ? N15 S4 C20 F11 59.2(16) . . . . ? O7 S4 C20 F10 51(2) . . . . ? O8 S4 C20 F10 176.2(18) . . . . ? N15 S4 C20 F10 -71.6(19) . . . . ? O7 S4 C20 F12 -63.9(14) . . . . ? O8 S4 C20 F12 61.0(16) . . . . ? N15 S4 C20 F12 173.3(13) . . . . ? #===END # Attachment 'CrystEngComm B609598D [emim]OTf.cif' # CIF-file generated for il12_150 in P b c a #=============================================================================== data_il12_150 _database_code_depnum_ccdc_archive 'CCDC 614038' # 0. AUDIT DETAILS _audit_creation_date 'Aug 04 14:01:15 2006' _audit_creation_method 'PLATON
option' _audit_update_record ; ? ; #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; 1-ethyl-3-methylimidazolium trifluoromethanesulfonate ; _chemical_name_common '1-ethyl-3-methylimidazolium trifluoromethanesulfonate' _chemical_melting_point ? _chemical_formula_moiety 'C6 H11 N2, C F3 O3 S' # Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)' _chemical_formula_structural ? _chemical_formula_sum 'C7 H11 F3 N2 O3 S' _chemical_formula_iupac ? _chemical_formula_weight 260.25 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source S S 0.1246 0.1234 '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' 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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_Hall '-P 2ac 2ab' _symmetry_space_group_name_H-M 'P b c a' _symmetry_Int_Tables_number 61 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 1/2-x,-y,1/2+z 3 1/2+x,1/2-y,-z 4 -x,1/2+y,1/2-z 5 -x,-y,-z 6 1/2+x,y,1/2-z 7 1/2-x,1/2+y,z 8 x,1/2-y,1/2+z _cell_length_a 10.183(5) _cell_length_b 12.384(7) _cell_length_c 18.294(8) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2307(2) _cell_formula_units_Z 8 _cell_measurement_temperature 150 _cell_measurement_reflns_used 739 _cell_measurement_theta_min 2.19 _cell_measurement_theta_max 17.83 _cell_special_details ; ? ; _exptl_crystal_description Rod _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.3 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.499 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 1072 _exptl_absorpt_coefficient_mu 0.316 _exptl_crystal_density_meas_temp ? # Permitted for _exptl_absorpt_correction_type : # analytical 'analytical from crystal shape' # Example: de Meulenaer&Tompa: ABST # cylinder 'cylindrical' # gaussian 'Gaussian from crystal shape' # Example: PLATON/ABSG # integration 'integration from crystal shape' # multi-scan 'symmetry-related measurements' # Example: SADABS, MULABS # none 'no absorption corr. applied' # numerical 'numerical from crystal shape' # psi-scan 'psi-scan corrections' # Example: PLATON/ABSP # refdelf 'refined from delta-F' # Example: SHELXA, DIFABS, DELABS # sphere 'spherical' # Example: PLATON/ABSS _exptl_absorpt_correction_type None # Example: '(North, Phillips & Mathews, 1968)' _exptl_absorpt_process_details ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ? ; _diffrn_ambient_temperature 150.0(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 'Bruker SMART CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? # number of measured reflections (redundant set) _diffrn_reflns_number 10196 _diffrn_reflns_av_R_equivalents 0.0404 _diffrn_reflns_av_sigmaI/netI 0.0363 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.23 _diffrn_reflns_theta_max 25.34 _reflns_number_total 2028 _reflns_number_gt 1535 _reflns_threshold_expression >2sigma(I) _diffrn_measured_fraction_theta_max 0.959 _diffrn_reflns_theta_full 25.34 _diffrn_measured_fraction_theta_full 0.959 _computing_data_collection 'Bruker SMART V5.628, (Bruker, 2004)' _computing_cell_refinement 'Bruker SMART V5.628, (Bruker, 2004)' _computing_data_reduction 'Bruker SAINT V6.45a, (Bruker, 2004)' _computing_structure_solution 'SIR92 (Altomare, 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; Ortep-32 for Windows (Farrugia, 1997), POV-Ray^TM^ for Windows Version 3.6 (The POV-Ray Team, 2004) and CAMERON (Watkin et. al., 1993) ; _computing_publication_material 'PLATON (Spek, 1990)' #=============================================================================== # 8. REFINEMENT DATA _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^)+(0.0358P)^2^+4.3360P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2028 _refine_ls_number_parameters 147 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0738 _refine_ls_R_factor_gt 0.0519 _refine_ls_wR_factor_ref 0.1341 _refine_ls_wR_factor_gt 0.1249 _refine_ls_goodness_of_fit_ref 1.139 _refine_ls_restrained_S_all 1.139 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.350 _refine_diff_density_min -0.286 _refine_diff_density_rms 0.066 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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 0.02018(9) 0.30651(7) 0.15056(5) 0.0308(3) Uani 1 1 d . . . F3 F 0.1410(3) 0.2493(2) 0.03140(13) 0.0742(9) Uani 1 1 d . . . F2 F -0.0624(3) 0.2826(3) 0.01643(14) 0.0827(10) Uani 1 1 d . . . F1 F 0.0735(3) 0.4117(2) 0.03107(14) 0.0759(9) Uani 1 1 d . . . O1 O -0.0832(2) 0.3828(2) 0.16363(15) 0.0444(7) Uani 1 1 d . . . O2 O -0.0129(3) 0.1967(2) 0.16358(14) 0.0450(7) Uani 1 1 d . . . O3 O 0.1456(2) 0.3398(2) 0.17835(14) 0.0400(7) Uani 1 1 d . . . N1 N 0.5597(3) 0.3207(2) 0.15552(16) 0.0361(7) Uani 1 1 d . . . C2 C 0.4388(4) 0.2849(3) 0.16102(18) 0.0310(8) Uani 1 1 d . . . H2 H 0.3642 0.3278 0.1650 0.037 Uiso 1 1 calc R . . N3 N 0.4401(3) 0.1779(2) 0.15994(16) 0.0363(7) Uani 1 1 d . . . C4 C 0.5670(3) 0.1444(3) 0.15449(19) 0.0342(8) Uani 1 1 d . . . H4 H 0.5961 0.0733 0.1528 0.041 Uiso 1 1 calc R . . C5 C 0.6422(4) 0.2335(3) 0.1520(2) 0.0379(9) Uani 1 1 d . . . H5 H 0.7333 0.2355 0.1486 0.045 Uiso 1 1 calc R . . C6 C 0.5976(4) 0.4351(3) 0.1538(2) 0.0425(10) Uani 1 1 d . . . H6A H 0.6698 0.4467 0.1875 0.051 Uiso 1 1 calc R . . H6B H 0.5241 0.4788 0.1700 0.051 Uiso 1 1 calc R . . C7 C 0.6384(5) 0.4706(3) 0.0786(2) 0.0552(12) Uani 1 1 d . . . H7A H 0.7123 0.4286 0.0628 0.083 Uiso 1 1 calc R . . H7B H 0.6622 0.5456 0.0797 0.083 Uiso 1 1 calc R . . H7C H 0.5667 0.4604 0.0452 0.083 Uiso 1 1 calc R . . C8 C 0.3255(4) 0.1083(3) 0.1644(3) 0.0513(11) Uani 1 1 d . . . H8A H 0.2547 0.1467 0.1873 0.077 Uiso 1 1 calc R . . H8B H 0.3465 0.0454 0.1927 0.077 Uiso 1 1 calc R . . H8C H 0.2997 0.0868 0.1160 0.077 Uiso 1 1 calc R . . C9 C 0.0437(5) 0.3128(4) 0.0526(2) 0.0491(11) 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 0.0296(5) 0.0326(5) 0.0303(4) 0.0000(4) 0.0000(4) 0.0030(4) F1 0.114(2) 0.0643(19) 0.0492(15) 0.0215(13) 0.0132(15) 0.0005(17) F2 0.085(2) 0.119(3) 0.0445(15) -0.0093(15) -0.0278(14) -0.0042(19) F3 0.093(2) 0.082(2) 0.0476(14) -0.0086(13) 0.0239(15) 0.0267(17) O1 0.0341(15) 0.0446(16) 0.0545(17) -0.0027(13) 0.0050(13) 0.0107(12) O2 0.0488(17) 0.0379(15) 0.0482(15) 0.0007(13) 0.0025(13) -0.0086(13) O3 0.0327(15) 0.0420(16) 0.0453(15) -0.0029(12) -0.0039(12) -0.0018(12) N1 0.0325(18) 0.0387(19) 0.0372(16) -0.0072(14) -0.0047(14) 0.0047(14) C2 0.030(2) 0.027(2) 0.0357(19) -0.0015(15) 0.0000(15) 0.0044(15) N3 0.0346(18) 0.039(2) 0.0357(16) 0.0026(14) -0.0018(13) -0.0013(14) C4 0.032(2) 0.033(2) 0.0376(19) -0.0026(16) 0.0007(16) 0.0086(16) C5 0.030(2) 0.040(2) 0.043(2) -0.0030(18) -0.0027(18) 0.0071(17) C6 0.041(2) 0.031(2) 0.056(2) -0.0088(18) -0.003(2) 0.0002(17) C7 0.070(3) 0.040(2) 0.055(3) 0.005(2) -0.017(2) -0.001(2) C8 0.040(2) 0.040(2) 0.075(3) 0.009(2) 0.004(2) 0.0001(19) C9 0.062(3) 0.051(3) 0.0339(19) 0.0000(19) -0.004(2) 0.009(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 S1 O2 1.421(3) . ? S1 O1 1.434(3) . ? S1 O3 1.435(3) . ? S1 C9 1.809(4) . ? N3 C2 1.325(5) . ? N3 C4 1.361(5) . ? N3 C8 1.454(5) . ? C2 N1 1.312(5) . ? C2 H2 0.9300 . ? N1 C5 1.370(5) . ? N1 C6 1.468(5) . ? C4 C5 1.343(5) . ? C4 H4 0.9300 . ? F3 C9 1.322(5) . ? F2 C9 1.321(5) . ? F1 C9 1.322(5) . ? C6 C7 1.503(6) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C5 H5 0.9300 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? 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 O2 S1 O1 115.39(17) . . ? O2 S1 O3 115.25(16) . . ? O1 S1 O3 113.85(16) . . ? O2 S1 C9 103.79(18) . . ? O1 S1 C9 103.54(18) . . ? O3 S1 C9 102.74(19) . . ? C2 N3 C4 108.4(3) . . ? C2 N3 C8 125.8(3) . . ? C4 N3 C8 125.8(3) . . ? N1 C2 N3 109.1(3) . . ? N1 C2 H2 125.4 . . ? N3 C2 H2 125.4 . . ? C2 N1 C5 108.2(3) . . ? C2 N1 C6 125.1(3) . . ? C5 N1 C6 126.7(3) . . ? C5 C4 N3 107.1(3) . . ? C5 C4 H4 126.5 . . ? N3 C4 H4 126.5 . . ? N1 C6 C7 112.0(3) . . ? N1 C6 H6A 109.2 . . ? C7 C6 H6A 109.2 . . ? N1 C6 H6B 109.2 . . ? C7 C6 H6B 109.2 . . ? H6A C6 H6B 107.9 . . ? C4 C5 N1 107.2(3) . . ? C4 C5 H5 126.4 . . ? N1 C5 H5 126.4 . . ? F2 C9 F1 107.5(4) . . ? F2 C9 F3 107.3(3) . . ? F1 C9 F3 106.9(4) . . ? F2 C9 S1 112.1(3) . . ? F1 C9 S1 111.4(3) . . ? F3 C9 S1 111.4(3) . . ? N3 C8 H8A 109.5 . . ? N3 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N3 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? 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 C4 N3 C2 N1 0.8(4) . . . . ? C8 N3 C2 N1 -179.6(3) . . . . ? N3 C2 N1 C5 -1.1(4) . . . . ? N3 C2 N1 C6 179.2(3) . . . . ? C2 N3 C4 C5 -0.2(4) . . . . ? C8 N3 C4 C5 -179.8(4) . . . . ? C2 N1 C6 C7 -106.3(4) . . . . ? C5 N1 C6 C7 74.0(5) . . . . ? N3 C4 C5 N1 -0.4(4) . . . . ? C2 N1 C5 C4 0.9(4) . . . . ? C6 N1 C5 C4 -179.3(3) . . . . ? O2 S1 C9 F2 58.5(3) . . . . ? O1 S1 C9 F2 -62.4(3) . . . . ? O3 S1 C9 F2 178.9(3) . . . . ? O2 S1 C9 F1 179.0(3) . . . . ? O1 S1 C9 F1 58.1(4) . . . . ? O3 S1 C9 F1 -60.6(3) . . . . ? O2 S1 C9 F3 -61.7(3) . . . . ? O1 S1 C9 F3 177.4(3) . . . . ? O3 S1 C9 F3 58.7(3) . . . . ? #===END