# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_CBA09-2a #============================================================================== # 2a #============================================================================== _audit_creation_date '07 April 2012' _audit_creation_method SHELXL-97 #============================================================================== # CHEMICAL DATA #============================================================================== _chemical_name_systematic ; 2-(Pyridin-1-ium-1-yl)-1,1-bis((trifluoromethyl)sulfonyl)ethan-1-ide ; _chemical_name_common ? _chemical_melting_point 446 _chemical_formula_moiety 'C9 H7 F6 N O4 S2' _chemical_formula_sum 'C9 H7 F6 N O4 S2' _chemical_formula_weight 371.28 _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_absolute_configuration . 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #============================================================================== # CRYSTAL DATA #============================================================================== _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' 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 14.8808(6) _cell_length_b 10.4392(5) _cell_length_c 42.5523(18) _cell_angle_alpha 90.00 _cell_angle_beta 91.5270(10) _cell_angle_gamma 90.00 _cell_volume 6607.9(5) _cell_formula_units_Z 20 _cell_measurement_temperature 90 _cell_measurement_reflns_used 9890 _cell_measurement_theta_min 2.38 _cell_measurement_theta_max 27.59 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.866 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3720 _exptl_absorpt_coefficient_mu 0.493 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.8907 _exptl_absorpt_correction_T_max 0.9432 _exptl_absorpt_process_details ; Crystal Faces plugin in Bruker APEX2 software ; _exptl_special_details ; ? ; #============================================================================== # EXPERIMENTAL DATA #============================================================================== _diffrn_ambient_temperature 90 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker TXS fine-focus rotating anode' _diffrn_radiation_monochromator 'Bruker Helios multilayer confocal mirror' _diffrn_measurement_device_type 'Bruker APEXII CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.333 _diffrn_reflns_number 30937 _diffrn_reflns_av_R_equivalents 0.0249 _diffrn_reflns_av_sigmaI/netI 0.0294 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -42 _diffrn_reflns_limit_l_max 50 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 25.03 _reflns_number_total 11691 _reflns_number_gt 10248 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2006)' _computing_cell_refinement 'APEX2 (Bruker AXS, 2006)' _computing_data_reduction 'SAINT (Bruker AXS, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSHEL (Bruker AXS,2002)' _computing_publication_material 'XCIF (Bruker AXS, 2001)' _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^)+(0.0344P)^2^+4.1562P] 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 11691 _refine_ls_number_parameters 991 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0368 _refine_ls_R_factor_gt 0.0307 _refine_ls_wR_factor_ref 0.0767 _refine_ls_wR_factor_gt 0.0733 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.30657(13) 0.0207(2) 0.86693(5) 0.0181(5) Uani 1 1 d . . . H1 H 0.3002 0.0698 0.8855 0.022 Uiso 1 1 calc R . . C2 C 0.32094(14) -0.1088(2) 0.86913(5) 0.0202(5) Uani 1 1 d . . . H2 H 0.3239 -0.1496 0.8891 0.024 Uiso 1 1 calc R . . C3 C 0.33108(14) -0.1793(2) 0.84186(5) 0.0198(5) Uani 1 1 d . . . H3 H 0.3409 -0.2691 0.8429 0.024 Uiso 1 1 calc R . . C4 C 0.32676(14) -0.1174(2) 0.81307(5) 0.0201(5) Uani 1 1 d . . . H4 H 0.3342 -0.1643 0.7942 0.024 Uiso 1 1 calc R . . C5 C 0.31176(13) 0.0118(2) 0.81200(5) 0.0188(5) Uani 1 1 d . . . H5 H 0.3087 0.0546 0.7923 0.023 Uiso 1 1 calc R . . C6 C 0.28437(14) 0.2211(2) 0.83725(5) 0.0183(5) Uani 1 1 d . . . H6A H 0.2752 0.2534 0.8588 0.022 Uiso 1 1 calc R . . H6B H 0.3384 0.2638 0.8291 0.022 Uiso 1 1 calc R . . C7 C 0.20467(13) 0.2573(2) 0.81694(5) 0.0150(4) Uani 1 1 d . . . C8 C 0.05606(14) 0.0876(2) 0.81375(5) 0.0185(5) Uani 1 1 d . . . C9 C 0.24749(14) 0.5011(2) 0.79340(5) 0.0189(5) Uani 1 1 d . . . C1B C 0.51078(13) 1.0364(2) 0.73470(5) 0.0150(4) Uani 1 1 d . . . H1B H 0.4997 0.9885 0.7160 0.018 Uiso 1 1 calc R . . C2B C 0.48570(13) 1.1630(2) 0.73601(5) 0.0174(5) Uani 1 1 d . . . H2B H 0.4571 1.2027 0.7183 0.021 Uiso 1 1 calc R . . C3B C 0.50249(13) 1.2323(2) 0.76332(5) 0.0181(5) Uani 1 1 d . . . H3B H 0.4850 1.3196 0.7646 0.022 Uiso 1 1 calc R . . C4B C 0.54489(15) 1.1730(2) 0.78862(5) 0.0214(5) Uani 1 1 d . . . H4B H 0.5579 1.2195 0.8074 0.026 Uiso 1 1 calc R . . C5B C 0.56811(15) 1.0457(2) 0.78644(5) 0.0205(5) Uani 1 1 d . . . H5B H 0.5965 1.0041 0.8039 0.025 Uiso 1 1 calc R . . C6B C 0.57032(14) 0.8369(2) 0.75734(5) 0.0163(4) Uani 1 1 d . . . H6B1 H 0.5131 0.7900 0.7597 0.020 Uiso 1 1 calc R . . H6B2 H 0.5915 0.8193 0.7359 0.020 Uiso 1 1 calc R . . C7B C 0.63780(13) 0.7840(2) 0.78050(5) 0.0132(4) Uani 1 1 d . . . C8B C 0.55852(14) 0.5577(2) 0.80445(5) 0.0191(5) Uani 1 1 d . . . C9B C 0.80793(14) 0.9047(2) 0.78888(5) 0.0168(5) Uani 1 1 d . . . C1C C 0.90170(13) 0.4123(2) 0.88274(5) 0.0147(4) Uani 1 1 d . . . H1C H 0.9339 0.4539 0.8994 0.018 Uiso 1 1 calc R . . C2C C 0.88723(13) 0.2819(2) 0.88409(5) 0.0165(4) Uani 1 1 d . . . H2C H 0.9095 0.2336 0.9015 0.020 Uiso 1 1 calc R . . C3C C 0.84018(13) 0.2224(2) 0.85991(5) 0.0169(4) Uani 1 1 d . . . H3C H 0.8293 0.1328 0.8606 0.020 Uiso 1 1 calc R . . C4C C 0.80870(13) 0.2948(2) 0.83445(5) 0.0164(4) Uani 1 1 d . . . H4C H 0.7764 0.2550 0.8175 0.020 Uiso 1 1 calc R . . C5C C 0.82477(13) 0.4239(2) 0.83403(5) 0.0147(4) Uani 1 1 d . . . H5C H 0.8036 0.4739 0.8167 0.018 Uiso 1 1 calc R . . C6C C 0.88083(14) 0.6262(2) 0.85623(5) 0.0154(4) Uani 1 1 d . . . H6C1 H 0.9061 0.6477 0.8356 0.018 Uiso 1 1 calc R . . H6C2 H 0.8202 0.6650 0.8569 0.018 Uiso 1 1 calc R . . C7C C 0.93835(13) 0.6870(2) 0.88126(5) 0.0136(4) Uani 1 1 d . . . C8C C 0.83799(14) 0.8861(2) 0.90967(5) 0.0163(4) Uani 1 1 d . . . C9C C 1.12156(13) 0.6169(2) 0.88936(5) 0.0169(5) Uani 1 1 d . . . C1D C 0.61215(13) 0.5885(2) 0.90978(5) 0.0164(5) Uani 1 1 d . . . H1D H 0.6153 0.5467 0.8900 0.020 Uiso 1 1 calc R . . C2D C 0.60826(14) 0.7195(2) 0.91102(5) 0.0193(5) Uani 1 1 d . . . H2D H 0.6082 0.7687 0.8922 0.023 Uiso 1 1 calc R . . C3D C 0.60446(14) 0.7795(2) 0.94001(5) 0.0201(5) Uani 1 1 d . . . H3D H 0.6012 0.8703 0.9413 0.024 Uiso 1 1 calc R . . C4D C 0.60550(15) 0.7060(2) 0.96718(5) 0.0209(5) Uani 1 1 d . . . H4D H 0.6039 0.7460 0.9872 0.025 Uiso 1 1 calc R . . C5D C 0.60892(13) 0.5750(2) 0.96482(5) 0.0179(5) Uani 1 1 d . . . H5D H 0.6094 0.5240 0.9833 0.022 Uiso 1 1 calc R . . C6D C 0.61067(13) 0.3742(2) 0.93436(5) 0.0170(5) Uani 1 1 d . . . H6D1 H 0.6670 0.3448 0.9248 0.020 Uiso 1 1 calc R . . H6D2 H 0.6088 0.3382 0.9559 0.020 Uiso 1 1 calc R . . C7D C 0.53226(13) 0.3240(2) 0.91529(5) 0.0135(4) Uani 1 1 d . . . C8D C 0.37103(13) 0.4689(2) 0.91510(5) 0.0182(5) Uani 1 1 d . . . C9D C 0.58442(16) 0.0896(2) 0.88841(5) 0.0246(5) Uani 1 1 d . . . C1E C 0.13018(13) 1.1114(2) 0.93685(5) 0.0154(4) Uani 1 1 d . . . H1E H 0.1226 1.0630 0.9181 0.018 Uiso 1 1 calc R . . C2E C 0.14046(15) 1.2423(2) 0.93529(5) 0.0197(5) Uani 1 1 d . . . H2E H 0.1404 1.2843 0.9155 0.024 Uiso 1 1 calc R . . C3E C 0.15093(14) 1.3122(2) 0.96287(5) 0.0182(5) Uani 1 1 d . . . H3E H 0.1590 1.4024 0.9621 0.022 Uiso 1 1 calc R . . C4E C 0.14960(14) 1.2495(2) 0.99145(5) 0.0170(5) Uani 1 1 d . . . H4E H 0.1558 1.2961 1.0106 0.020 Uiso 1 1 calc R . . C5E C 0.13910(14) 1.1185(2) 0.99182(5) 0.0166(4) Uani 1 1 d . . . H5E H 0.1376 1.0747 1.0114 0.020 Uiso 1 1 calc R . . C6E C 0.11814(14) 0.9075(2) 0.96593(5) 0.0151(4) Uani 1 1 d . . . H6E1 H 0.0559 0.8886 0.9721 0.018 Uiso 1 1 calc R . . H6E2 H 0.1261 0.8722 0.9446 0.018 Uiso 1 1 calc R . . C7E C 0.18215(13) 0.84154(19) 0.98832(5) 0.0130(4) Uani 1 1 d . . . C8E C 0.36453(14) 0.9244(2) 0.99071(5) 0.0208(5) Uani 1 1 d . . . C9E C 0.10209(14) 0.6280(2) 1.01813(5) 0.0165(4) Uani 1 1 d . . . F1 F 0.31776(8) 0.50621(13) 0.81366(3) 0.0261(3) Uani 1 1 d . . . F2 F 0.26886(10) 0.56736(13) 0.76798(3) 0.0332(3) Uani 1 1 d . . . F3 F 0.17850(8) 0.55780(12) 0.80674(3) 0.0264(3) Uani 1 1 d . . . F4 F 0.11285(8) -0.00852(12) 0.81839(3) 0.0270(3) Uani 1 1 d . . . F5 F -0.02105(8) 0.05796(13) 0.82712(3) 0.0276(3) Uani 1 1 d . . . F6 F 0.04071(9) 0.10004(14) 0.78299(3) 0.0301(3) Uani 1 1 d . . . F1B F 0.62421(8) 0.47918(12) 0.79604(3) 0.0280(3) Uani 1 1 d . . . F2B F 0.51877(8) 0.50774(13) 0.82925(3) 0.0281(3) Uani 1 1 d . . . F3B F 0.49771(8) 0.56248(13) 0.78083(3) 0.0266(3) Uani 1 1 d . . . F4B F 0.89249(8) 0.90267(14) 0.78001(3) 0.0306(3) Uani 1 1 d . . . F5B F 0.77222(9) 1.01608(12) 0.78029(3) 0.0305(3) Uani 1 1 d . . . F6B F 0.80723(9) 0.89721(13) 0.81997(3) 0.0253(3) Uani 1 1 d . . . F1C F 0.77989(8) 0.88474(12) 0.88516(3) 0.0213(3) Uani 1 1 d . . . F2C F 0.79294(8) 0.91779(12) 0.93528(3) 0.0207(3) Uani 1 1 d . . . F3C F 0.89855(8) 0.97730(12) 0.90460(3) 0.0239(3) Uani 1 1 d . . . F4C F 1.10360(8) 0.50048(12) 0.87779(3) 0.0259(3) Uani 1 1 d . . . F5C F 1.11765(8) 0.61004(13) 0.92050(3) 0.0238(3) Uani 1 1 d . . . F6C F 1.20537(8) 0.64723(13) 0.88188(3) 0.0246(3) Uani 1 1 d . . . F1D F 0.36225(9) 0.46515(14) 0.88398(3) 0.0293(3) Uani 1 1 d . . . F2D F 0.28942(8) 0.47531(13) 0.92704(3) 0.0281(3) Uani 1 1 d . . . F3D F 0.41502(8) 0.57522(12) 0.92303(3) 0.0266(3) Uani 1 1 d . . . F4D F 0.65375(9) 0.08539(13) 0.90877(3) 0.0282(3) Uani 1 1 d . . . F5D F 0.51770(10) 0.02179(13) 0.90027(4) 0.0371(4) Uani 1 1 d . . . F6D F 0.60975(11) 0.03253(15) 0.86191(3) 0.0422(4) Uani 1 1 d . . . F1E F 0.33748(9) 1.04082(13) 0.98204(4) 0.0339(3) Uani 1 1 d . . . F2E F 0.44545(8) 0.90469(14) 0.97896(3) 0.0332(3) Uani 1 1 d . . . F3E F 0.37318(9) 0.92308(14) 1.02187(3) 0.0318(3) Uani 1 1 d . . . F4E F 0.05590(8) 0.59339(12) 1.04339(3) 0.0223(3) Uani 1 1 d . . . F5E F 0.04667(9) 0.62096(12) 0.99309(3) 0.0258(3) Uani 1 1 d . . . F6E F 0.16764(9) 0.54311(12) 1.01457(3) 0.0262(3) Uani 1 1 d . . . N1 N 0.30131(11) 0.07912(17) 0.83880(4) 0.0156(4) Uani 1 1 d . . . N1B N 0.55113(11) 0.97978(17) 0.75991(4) 0.0135(4) Uani 1 1 d . . . N1C N 0.87058(10) 0.48097(17) 0.85811(4) 0.0129(4) Uani 1 1 d . . . N1D N 0.61160(11) 0.51820(17) 0.93640(4) 0.0142(4) Uani 1 1 d . . . N1E N 0.13089(11) 1.05183(17) 0.96487(4) 0.0132(4) Uani 1 1 d . . . O1 O 0.30555(9) 0.29183(15) 0.76997(3) 0.0209(3) Uani 1 1 d . . . O2 O 0.14253(9) 0.34275(15) 0.76322(3) 0.0179(3) Uani 1 1 d . . . O3 O 0.11017(10) 0.20502(15) 0.86393(3) 0.0203(3) Uani 1 1 d . . . O4 O 0.03589(9) 0.33143(14) 0.82088(3) 0.0179(3) Uani 1 1 d . . . O1B O 0.67161(9) 0.69518(15) 0.83694(3) 0.0192(3) Uani 1 1 d . . . O2B O 0.52085(10) 0.78438(15) 0.82299(4) 0.0227(3) Uani 1 1 d . . . O3B O 0.79068(9) 0.65953(14) 0.78333(3) 0.0163(3) Uani 1 1 d . . . O4B O 0.75287(10) 0.79817(15) 0.73726(3) 0.0195(3) Uani 1 1 d . . . O1C O 0.81476(9) 0.64563(14) 0.92012(3) 0.0181(3) Uani 1 1 d . . . O2C O 0.95449(9) 0.75027(14) 0.94061(3) 0.0173(3) Uani 1 1 d . . . O3C O 1.05539(10) 0.72587(15) 0.83962(3) 0.0199(3) Uani 1 1 d . . . O4C O 1.06925(9) 0.85163(14) 0.88939(3) 0.0173(3) Uani 1 1 d . . . O1D O 0.37142(10) 0.22317(15) 0.92001(4) 0.0227(3) Uani 1 1 d . . . O2D O 0.43906(10) 0.35356(15) 0.96372(3) 0.0231(4) Uani 1 1 d . . . O3D O 0.63063(9) 0.30903(16) 0.86710(3) 0.0229(4) Uani 1 1 d . . . O4D O 0.47058(9) 0.24141(15) 0.86122(3) 0.0188(3) Uani 1 1 d . . . O1E O 0.28760(10) 0.81901(16) 0.94260(3) 0.0229(4) Uani 1 1 d . . . O2E O 0.32036(9) 0.68577(14) 0.99020(3) 0.0194(3) Uani 1 1 d . . . O3E O 0.06617(9) 0.86305(14) 1.03079(3) 0.0167(3) Uani 1 1 d . . . O4E O 0.21657(9) 0.77642(14) 1.04664(3) 0.0163(3) Uani 1 1 d . . . S1 S 0.10048(3) 0.23745(5) 0.831131(11) 0.01353(11) Uani 1 1 d . . . S2 S 0.22220(3) 0.33353(5) 0.782907(12) 0.01391(11) Uani 1 1 d . . . S1B S 0.60095(3) 0.71883(5) 0.814020(12) 0.01422(11) Uani 1 1 d . . . S2B S 0.74619(3) 0.76968(5) 0.770119(11) 0.01268(11) Uani 1 1 d . . . S1C S 0.89077(3) 0.72783(5) 0.915377(11) 0.01274(11) Uani 1 1 d . . . S2C S 1.04305(3) 0.73722(5) 0.872881(12) 0.01339(11) Uani 1 1 d . . . S1D S 0.42905(3) 0.32498(5) 0.930765(12) 0.01512(11) Uani 1 1 d . . . S2D S 0.55066(3) 0.25609(5) 0.880327(12) 0.01498(12) Uani 1 1 d . . . S1E S 0.28557(3) 0.80059(5) 0.975938(12) 0.01483(11) Uani 1 1 d . . . S2E S 0.14595(3) 0.79203(5) 1.023397(11) 0.01224(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 C1 0.0165(11) 0.0236(12) 0.0143(11) -0.0013(9) -0.0015(8) -0.0021(9) C2 0.0213(11) 0.0225(12) 0.0170(11) 0.0039(9) 0.0019(9) -0.0024(9) C3 0.0171(11) 0.0192(12) 0.0232(12) 0.0021(10) 0.0016(9) 0.0016(9) C4 0.0183(11) 0.0269(13) 0.0153(11) -0.0031(10) 0.0023(9) 0.0067(9) C5 0.0171(11) 0.0247(13) 0.0147(11) 0.0033(9) 0.0008(8) 0.0032(9) C6 0.0175(11) 0.0154(11) 0.0219(12) 0.0010(9) -0.0041(9) 0.0000(9) C7 0.0124(10) 0.0159(11) 0.0165(11) 0.0012(9) -0.0012(8) -0.0003(8) C8 0.0174(11) 0.0201(12) 0.0182(11) -0.0009(9) 0.0022(9) -0.0019(9) C9 0.0187(11) 0.0175(12) 0.0204(12) 0.0028(9) -0.0010(9) -0.0017(9) C1B 0.0107(10) 0.0189(11) 0.0153(11) 0.0008(9) -0.0013(8) -0.0016(8) C2B 0.0142(10) 0.0177(11) 0.0203(11) 0.0043(9) -0.0022(8) -0.0006(9) C3B 0.0136(10) 0.0172(11) 0.0237(12) 0.0009(9) 0.0048(9) 0.0002(9) C4B 0.0277(12) 0.0197(12) 0.0167(11) -0.0040(9) 0.0023(9) 0.0030(10) C5B 0.0269(12) 0.0216(12) 0.0128(11) -0.0009(9) -0.0046(9) 0.0031(10) C6B 0.0186(11) 0.0135(11) 0.0164(11) -0.0012(9) -0.0046(8) 0.0035(9) C7B 0.0135(10) 0.0125(10) 0.0135(10) 0.0003(8) -0.0014(8) -0.0001(8) C8B 0.0168(11) 0.0211(12) 0.0194(12) 0.0040(9) -0.0022(9) -0.0026(9) C9B 0.0176(11) 0.0162(11) 0.0167(11) 0.0011(9) 0.0013(8) -0.0031(9) C1C 0.0154(10) 0.0176(11) 0.0111(10) -0.0010(9) -0.0016(8) 0.0016(9) C2C 0.0170(10) 0.0180(11) 0.0147(11) 0.0024(9) 0.0020(8) 0.0014(9) C3C 0.0181(11) 0.0147(11) 0.0183(11) 0.0001(9) 0.0062(8) -0.0021(9) C4C 0.0151(10) 0.0202(12) 0.0140(11) -0.0025(9) 0.0012(8) -0.0031(9) C5C 0.0132(10) 0.0193(11) 0.0116(10) 0.0003(9) -0.0003(8) -0.0005(8) C6C 0.0197(11) 0.0117(11) 0.0145(11) 0.0010(8) -0.0039(8) 0.0014(9) C7C 0.0141(10) 0.0144(11) 0.0122(10) -0.0016(8) -0.0005(8) 0.0028(8) C8C 0.0199(11) 0.0154(11) 0.0135(11) -0.0012(9) -0.0006(8) 0.0019(9) C9C 0.0155(10) 0.0178(11) 0.0176(11) 0.0012(9) 0.0008(8) 0.0015(9) C1D 0.0134(10) 0.0231(12) 0.0127(11) -0.0008(9) -0.0001(8) -0.0015(9) C2D 0.0201(11) 0.0206(12) 0.0173(11) 0.0024(9) 0.0014(9) -0.0038(9) C3D 0.0214(11) 0.0167(12) 0.0225(12) -0.0014(10) 0.0032(9) -0.0032(9) C4D 0.0265(12) 0.0215(12) 0.0148(11) -0.0032(9) 0.0018(9) -0.0026(10) C5D 0.0173(11) 0.0226(12) 0.0137(11) -0.0003(9) -0.0011(8) -0.0026(9) C6D 0.0157(10) 0.0160(11) 0.0192(11) -0.0013(9) -0.0035(8) 0.0040(9) C7D 0.0141(10) 0.0143(11) 0.0119(10) -0.0015(8) -0.0010(8) 0.0017(8) C8D 0.0134(10) 0.0207(12) 0.0207(12) -0.0013(9) 0.0039(8) 0.0026(9) C9D 0.0305(13) 0.0218(13) 0.0209(12) -0.0072(10) -0.0095(10) 0.0104(10) C1E 0.0161(10) 0.0193(11) 0.0108(10) 0.0000(9) -0.0002(8) 0.0015(9) C2E 0.0268(12) 0.0186(12) 0.0139(11) 0.0041(9) 0.0023(9) -0.0005(9) C3E 0.0203(11) 0.0140(11) 0.0203(12) 0.0011(9) 0.0039(9) -0.0002(9) C4E 0.0223(11) 0.0154(11) 0.0133(11) -0.0035(9) 0.0019(8) -0.0003(9) C5E 0.0201(11) 0.0164(11) 0.0133(11) 0.0017(9) -0.0007(8) 0.0009(9) C6E 0.0201(11) 0.0110(11) 0.0140(11) 0.0002(8) -0.0048(8) -0.0014(9) C7E 0.0142(10) 0.0125(10) 0.0121(10) 0.0011(8) -0.0014(8) 0.0000(8) C8E 0.0180(11) 0.0221(12) 0.0226(12) -0.0002(10) 0.0030(9) -0.0018(9) C9E 0.0210(11) 0.0154(11) 0.0132(11) 0.0027(9) -0.0009(8) -0.0015(9) F1 0.0203(7) 0.0218(7) 0.0357(8) -0.0010(6) -0.0089(6) -0.0048(5) F2 0.0468(9) 0.0233(8) 0.0296(8) 0.0094(6) 0.0037(6) -0.0063(7) F3 0.0241(7) 0.0215(7) 0.0336(8) -0.0076(6) -0.0003(6) 0.0052(6) F4 0.0249(7) 0.0154(7) 0.0408(8) -0.0022(6) 0.0004(6) -0.0004(6) F5 0.0201(7) 0.0294(8) 0.0336(8) -0.0070(6) 0.0076(6) -0.0103(6) F6 0.0428(8) 0.0312(8) 0.0160(7) -0.0033(6) -0.0059(6) -0.0130(7) F1B 0.0261(7) 0.0181(7) 0.0398(8) -0.0030(6) 0.0031(6) 0.0025(6) F2B 0.0268(7) 0.0303(8) 0.0270(7) 0.0127(6) 0.0018(6) -0.0072(6) F3B 0.0277(7) 0.0260(8) 0.0254(7) 0.0049(6) -0.0114(6) -0.0096(6) F4B 0.0198(7) 0.0350(8) 0.0375(8) -0.0144(7) 0.0089(6) -0.0130(6) F5B 0.0389(8) 0.0136(7) 0.0383(8) 0.0010(6) -0.0103(6) -0.0028(6) F6B 0.0344(7) 0.0285(8) 0.0131(6) -0.0038(6) -0.0008(5) -0.0106(6) F1C 0.0256(7) 0.0215(7) 0.0164(6) -0.0012(5) -0.0065(5) 0.0098(5) F2C 0.0246(7) 0.0234(7) 0.0142(6) -0.0042(5) 0.0015(5) 0.0071(5) F3C 0.0269(7) 0.0132(7) 0.0319(7) 0.0015(6) 0.0028(6) -0.0001(5) F4C 0.0258(7) 0.0137(7) 0.0381(8) -0.0041(6) -0.0021(6) 0.0034(5) F5C 0.0231(7) 0.0300(8) 0.0182(7) 0.0063(6) 0.0006(5) 0.0083(6) F6C 0.0150(6) 0.0264(7) 0.0325(7) 0.0047(6) 0.0043(5) 0.0011(5) F1D 0.0355(8) 0.0332(8) 0.0192(7) 0.0025(6) -0.0011(6) 0.0149(6) F2D 0.0141(6) 0.0322(8) 0.0386(8) 0.0036(6) 0.0085(6) 0.0045(6) F3D 0.0194(6) 0.0162(7) 0.0442(8) -0.0016(6) 0.0009(6) 0.0012(5) F4D 0.0303(7) 0.0286(8) 0.0251(7) -0.0050(6) -0.0116(6) 0.0156(6) F5D 0.0394(8) 0.0183(7) 0.0530(10) 0.0056(7) -0.0120(7) -0.0004(6) F6D 0.0626(10) 0.0366(9) 0.0266(8) -0.0180(7) -0.0151(7) 0.0290(8) F1E 0.0280(7) 0.0186(7) 0.0550(10) 0.0023(7) -0.0011(7) -0.0054(6) F2E 0.0166(7) 0.0401(9) 0.0434(9) -0.0082(7) 0.0102(6) -0.0030(6) F3E 0.0320(8) 0.0430(9) 0.0202(7) -0.0077(6) -0.0009(6) -0.0144(7) F4E 0.0272(7) 0.0214(7) 0.0183(7) 0.0051(5) 0.0021(5) -0.0069(6) F5E 0.0366(8) 0.0208(7) 0.0193(7) 0.0026(6) -0.0113(6) -0.0111(6) F6E 0.0324(7) 0.0128(7) 0.0336(8) -0.0013(6) 0.0049(6) 0.0029(6) N1 0.0113(8) 0.0190(10) 0.0163(9) 0.0007(8) -0.0026(7) -0.0007(7) N1B 0.0129(8) 0.0143(9) 0.0131(9) -0.0004(7) -0.0002(7) 0.0010(7) N1C 0.0108(8) 0.0152(9) 0.0127(9) -0.0008(7) 0.0010(7) 0.0013(7) N1D 0.0109(8) 0.0172(9) 0.0146(9) -0.0007(7) -0.0008(7) 0.0001(7) N1E 0.0126(8) 0.0141(9) 0.0127(9) -0.0003(7) -0.0022(7) 0.0009(7) O1 0.0155(7) 0.0236(9) 0.0240(8) -0.0019(7) 0.0046(6) 0.0022(6) O2 0.0171(7) 0.0228(8) 0.0138(7) 0.0006(6) -0.0005(6) 0.0005(6) O3 0.0276(8) 0.0212(8) 0.0120(7) 0.0008(6) -0.0006(6) -0.0018(7) O4 0.0159(7) 0.0191(8) 0.0190(8) 0.0008(6) 0.0027(6) 0.0015(6) O1B 0.0168(7) 0.0270(9) 0.0136(8) 0.0017(7) -0.0019(6) -0.0014(6) O2B 0.0170(8) 0.0268(9) 0.0246(9) -0.0014(7) 0.0059(6) 0.0045(7) O3B 0.0145(7) 0.0152(8) 0.0191(8) 0.0001(6) 0.0010(6) 0.0010(6) O4B 0.0238(8) 0.0224(8) 0.0124(7) -0.0003(6) 0.0009(6) -0.0040(7) O1C 0.0155(7) 0.0180(8) 0.0208(8) 0.0019(6) 0.0019(6) -0.0004(6) O2C 0.0184(7) 0.0217(8) 0.0116(7) 0.0001(6) -0.0022(6) 0.0012(6) O3C 0.0246(8) 0.0218(8) 0.0136(8) -0.0002(6) 0.0019(6) 0.0001(7) O4C 0.0204(8) 0.0142(8) 0.0174(8) -0.0014(6) 0.0001(6) -0.0007(6) O1D 0.0207(8) 0.0205(8) 0.0270(9) -0.0015(7) 0.0021(6) -0.0069(7) O2D 0.0285(8) 0.0282(9) 0.0127(8) -0.0005(7) 0.0027(6) 0.0013(7) O3D 0.0157(7) 0.0324(10) 0.0208(8) -0.0002(7) 0.0040(6) 0.0035(7) O4D 0.0174(7) 0.0236(9) 0.0152(8) -0.0027(6) -0.0049(6) 0.0052(6) O1E 0.0289(9) 0.0276(9) 0.0123(8) -0.0003(7) 0.0029(6) 0.0004(7) O2E 0.0212(8) 0.0182(8) 0.0189(8) -0.0011(6) 0.0014(6) 0.0058(6) O3E 0.0151(7) 0.0169(8) 0.0181(8) -0.0023(6) 0.0012(6) 0.0015(6) O4E 0.0169(7) 0.0202(8) 0.0118(7) -0.0012(6) -0.0021(6) 0.0015(6) S1 0.0144(2) 0.0145(3) 0.0117(3) -0.0008(2) -0.00036(19) -0.0011(2) S2 0.0118(2) 0.0156(3) 0.0143(3) -0.0002(2) 0.00076(19) 0.0003(2) S1B 0.0121(2) 0.0173(3) 0.0132(3) 0.0003(2) 0.00008(19) 0.0002(2) S2B 0.0141(2) 0.0125(3) 0.0115(2) -0.0004(2) 0.00028(19) -0.0014(2) S1C 0.0138(2) 0.0125(3) 0.0118(3) 0.0004(2) -0.00113(19) 0.0017(2) S2C 0.0159(2) 0.0124(3) 0.0119(2) 0.0005(2) 0.00021(19) 0.0008(2) S1D 0.0164(3) 0.0160(3) 0.0131(3) 0.0004(2) 0.0018(2) -0.0003(2) S2D 0.0142(2) 0.0176(3) 0.0130(3) -0.0016(2) -0.00180(19) 0.0050(2) S1E 0.0172(3) 0.0150(3) 0.0124(3) -0.0013(2) 0.0016(2) 0.0009(2) S2E 0.0138(2) 0.0112(3) 0.0117(3) -0.0004(2) -0.00083(19) -0.0001(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 C1 N1 1.344(3) . ? C1 C2 1.371(3) . ? C1 H1 0.9500 . ? C2 C3 1.386(3) . ? C2 H2 0.9500 . ? C3 C4 1.385(3) . ? C3 H3 0.9500 . ? C4 C5 1.367(3) . ? C4 H4 0.9500 . ? C5 N1 1.352(3) . ? C5 H5 0.9500 . ? C6 C7 1.497(3) . ? C6 N1 1.504(3) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 S2 1.679(2) . ? C7 S1 1.692(2) . ? C8 F4 1.323(3) . ? C8 F6 1.329(2) . ? C8 F5 1.331(2) . ? C8 S1 1.846(2) . ? C9 F3 1.326(2) . ? C9 F2 1.330(2) . ? C9 F1 1.338(2) . ? C9 S2 1.842(2) . ? C1B N1B 1.351(3) . ? C1B C2B 1.375(3) . ? C1B H1B 0.9500 . ? C2B C3B 1.386(3) . ? C2B H2B 0.9500 . ? C3B C4B 1.380(3) . ? C3B H3B 0.9500 . ? C4B C5B 1.377(3) . ? C4B H4B 0.9500 . ? C5B N1B 1.340(3) . ? C5B H5B 0.9500 . ? C6B C7B 1.494(3) . ? C6B N1B 1.523(3) . ? C6B H6B1 0.9900 . ? C6B H6B2 0.9900 . ? C7B S1B 1.685(2) . ? C7B S2B 1.690(2) . ? C8B F2B 1.330(2) . ? C8B F1B 1.332(3) . ? C8B F3B 1.335(2) . ? C8B S1B 1.839(2) . ? C9B F4B 1.323(2) . ? C9B F6B 1.326(2) . ? C9B F5B 1.326(3) . ? C9B S2B 1.851(2) . ? C1C N1C 1.342(3) . ? C1C C2C 1.380(3) . ? C1C H1C 0.9500 . ? C2C C3C 1.377(3) . ? C2C H2C 0.9500 . ? C3C C4C 1.391(3) . ? C3C H3C 0.9500 . ? C4C C5C 1.370(3) . ? C4C H4C 0.9500 . ? C5C N1C 1.354(3) . ? C5C H5C 0.9500 . ? C6C C7C 1.490(3) . ? C6C N1C 1.526(3) . ? C6C H6C1 0.9900 . ? C6C H6C2 0.9900 . ? C7C S1C 1.687(2) . ? C7C S2C 1.691(2) . ? C8C F3C 1.332(2) . ? C8C F2C 1.336(2) . ? C8C F1C 1.337(2) . ? C8C S1C 1.843(2) . ? C9C F5C 1.330(2) . ? C9C F6C 1.333(2) . ? C9C F4C 1.336(2) . ? C9C S2C 1.841(2) . ? C1D N1D 1.350(3) . ? C1D C2D 1.370(3) . ? C1D H1D 0.9500 . ? C2D C3D 1.386(3) . ? C2D H2D 0.9500 . ? C3D C4D 1.387(3) . ? C3D H3D 0.9500 . ? C4D C5D 1.373(3) . ? C4D H4D 0.9500 . ? C5D N1D 1.348(3) . ? C5D H5D 0.9500 . ? C6D C7D 1.498(3) . ? C6D N1D 1.506(3) . ? C6D H6D1 0.9900 . ? C6D H6D2 0.9900 . ? C7D S2D 1.677(2) . ? C7D S1D 1.687(2) . ? C8D F1D 1.328(2) . ? C8D F3D 1.328(3) . ? C8D F2D 1.331(2) . ? C8D S1D 1.848(2) . ? C9D F5D 1.329(3) . ? C9D F4D 1.330(2) . ? C9D F6D 1.338(3) . ? C9D S2D 1.839(2) . ? C1E N1E 1.345(3) . ? C1E C2E 1.376(3) . ? C1E H1E 0.9500 . ? C2E C3E 1.387(3) . ? C2E H2E 0.9500 . ? C3E C4E 1.382(3) . ? C3E H3E 0.9500 . ? C4E C5E 1.377(3) . ? C4E H4E 0.9500 . ? C5E N1E 1.344(3) . ? C5E H5E 0.9500 . ? C6E C7E 1.497(3) . ? C6E N1E 1.519(3) . ? C6E H6E1 0.9900 . ? C6E H6E2 0.9900 . ? C7E S2E 1.682(2) . ? C7E S1E 1.695(2) . ? C8E F3E 1.329(3) . ? C8E F1E 1.330(3) . ? C8E F2E 1.332(2) . ? C8E S1E 1.845(2) . ? C9E F6E 1.330(2) . ? C9E F5E 1.332(2) . ? C9E F4E 1.341(2) . ? C9E S2E 1.844(2) . ? O1 S2 1.4378(15) . ? O2 S2 1.4365(14) . ? O3 S1 1.4394(15) . ? O4 S1 1.4333(15) . ? O1B S1B 1.4361(14) . ? O2B S1B 1.4349(15) . ? O3B S2B 1.4341(15) . ? O4B S2B 1.4355(14) . ? O1C S1C 1.4383(15) . ? O2C S1C 1.4327(14) . ? O3C S2C 1.4368(15) . ? O4C S2C 1.4345(15) . ? O1D S1D 1.4331(16) . ? O2D S1D 1.4377(15) . ? O3D S2D 1.4402(15) . ? O4D S2D 1.4326(14) . ? O1E S1E 1.4326(15) . ? O2E S1E 1.4340(15) . ? O3E S2E 1.4415(14) . ? O4E S2E 1.4331(14) . ? 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 C1 C2 120.9(2) . . ? N1 C1 H1 119.6 . . ? C2 C1 H1 119.6 . . ? C1 C2 C3 119.1(2) . . ? C1 C2 H2 120.4 . . ? C3 C2 H2 120.4 . . ? C4 C3 C2 119.3(2) . . ? C4 C3 H3 120.3 . . ? C2 C3 H3 120.3 . . ? C5 C4 C3 119.5(2) . . ? C5 C4 H4 120.2 . . ? C3 C4 H4 120.2 . . ? N1 C5 C4 120.5(2) . . ? N1 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C7 C6 N1 113.77(17) . . ? C7 C6 H6A 108.8 . . ? N1 C6 H6A 108.8 . . ? C7 C6 H6B 108.8 . . ? N1 C6 H6B 108.8 . . ? H6A C6 H6B 107.7 . . ? C6 C7 S2 118.59(15) . . ? C6 C7 S1 118.86(15) . . ? S2 C7 S1 122.06(12) . . ? F4 C8 F6 108.27(17) . . ? F4 C8 F5 108.34(18) . . ? F6 C8 F5 108.45(17) . . ? F4 C8 S1 111.25(14) . . ? F6 C8 S1 111.22(15) . . ? F5 C8 S1 109.22(14) . . ? F3 C9 F2 108.72(18) . . ? F3 C9 F1 107.90(17) . . ? F2 C9 F1 107.69(17) . . ? F3 C9 S2 111.85(14) . . ? F2 C9 S2 110.38(15) . . ? F1 C9 S2 110.18(15) . . ? N1B C1B C2B 120.2(2) . . ? N1B C1B H1B 119.9 . . ? C2B C1B H1B 119.9 . . ? C1B C2B C3B 119.5(2) . . ? C1B C2B H2B 120.2 . . ? C3B C2B H2B 120.2 . . ? C4B C3B C2B 119.2(2) . . ? C4B C3B H3B 120.4 . . ? C2B C3B H3B 120.4 . . ? C5B C4B C3B 119.4(2) . . ? C5B C4B H4B 120.3 . . ? C3B C4B H4B 120.3 . . ? N1B C5B C4B 120.7(2) . . ? N1B C5B H5B 119.7 . . ? C4B C5B H5B 119.7 . . ? C7B C6B N1B 116.02(17) . . ? C7B C6B H6B1 108.3 . . ? N1B C6B H6B1 108.3 . . ? C7B C6B H6B2 108.3 . . ? N1B C6B H6B2 108.3 . . ? H6B1 C6B H6B2 107.4 . . ? C6B C7B S1B 118.66(15) . . ? C6B C7B S2B 119.29(15) . . ? S1B C7B S2B 121.33(12) . . ? F2B C8B F1B 108.48(18) . . ? F2B C8B F3B 107.77(16) . . ? F1B C8B F3B 107.96(18) . . ? F2B C8B S1B 109.90(15) . . ? F1B C8B S1B 111.85(14) . . ? F3B C8B S1B 110.75(15) . . ? F4B C9B F6B 108.45(17) . . ? F4B C9B F5B 108.21(17) . . ? F6B C9B F5B 108.22(17) . . ? F4B C9B S2B 109.25(14) . . ? F6B C9B S2B 111.63(14) . . ? F5B C9B S2B 110.99(14) . . ? N1C C1C C2C 120.55(19) . . ? N1C C1C H1C 119.7 . . ? C2C C1C H1C 119.7 . . ? C3C C2C C1C 119.4(2) . . ? C3C C2C H2C 120.3 . . ? C1C C2C H2C 120.3 . . ? C2C C3C C4C 119.4(2) . . ? C2C C3C H3C 120.3 . . ? C4C C3C H3C 120.3 . . ? C5C C4C C3C 119.3(2) . . ? C5C C4C H4C 120.4 . . ? C3C C4C H4C 120.4 . . ? N1C C5C C4C 120.52(19) . . ? N1C C5C H5C 119.7 . . ? C4C C5C H5C 119.7 . . ? C7C C6C N1C 116.21(16) . . ? C7C C6C H6C1 108.2 . . ? N1C C6C H6C1 108.2 . . ? C7C C6C H6C2 108.2 . . ? N1C C6C H6C2 108.2 . . ? H6C1 C6C H6C2 107.4 . . ? C6C C7C S1C 118.46(15) . . ? C6C C7C S2C 119.74(15) . . ? S1C C7C S2C 120.88(12) . . ? F3C C8C F2C 108.16(17) . . ? F3C C8C F1C 107.93(17) . . ? F2C C8C F1C 108.11(16) . . ? F3C C8C S1C 111.97(14) . . ? F2C C8C S1C 109.60(14) . . ? F1C C8C S1C 110.94(14) . . ? F5C C9C F6C 108.46(16) . . ? F5C C9C F4C 107.72(17) . . ? F6C C9C F4C 107.87(16) . . ? F5C C9C S2C 111.86(14) . . ? F6C C9C S2C 109.60(14) . . ? F4C C9C S2C 111.20(14) . . ? N1D C1D C2D 120.6(2) . . ? N1D C1D H1D 119.7 . . ? C2D C1D H1D 119.7 . . ? C1D C2D C3D 119.2(2) . . ? C1D C2D H2D 120.4 . . ? C3D C2D H2D 120.4 . . ? C2D C3D C4D 119.5(2) . . ? C2D C3D H3D 120.3 . . ? C4D C3D H3D 120.3 . . ? C5D C4D C3D 119.4(2) . . ? C5D C4D H4D 120.3 . . ? C3D C4D H4D 120.3 . . ? N1D C5D C4D 120.4(2) . . ? N1D C5D H5D 119.8 . . ? C4D C5D H5D 119.8 . . ? C7D C6D N1D 112.73(16) . . ? C7D C6D H6D1 109.0 . . ? N1D C6D H6D1 109.0 . . ? C7D C6D H6D2 109.0 . . ? N1D C6D H6D2 109.0 . . ? H6D1 C6D H6D2 107.8 . . ? C6D C7D S2D 119.03(15) . . ? C6D C7D S1D 119.37(15) . . ? S2D C7D S1D 121.37(12) . . ? F1D C8D F3D 108.23(18) . . ? F1D C8D F2D 108.41(17) . . ? F3D C8D F2D 108.04(17) . . ? F1D C8D S1D 111.62(14) . . ? F3D C8D S1D 111.44(14) . . ? F2D C8D S1D 109.00(15) . . ? F5D C9D F4D 108.03(19) . . ? F5D C9D F6D 108.2(2) . . ? F4D C9D F6D 107.65(18) . . ? F5D C9D S2D 111.77(15) . . ? F4D C9D S2D 110.86(16) . . ? F6D C9D S2D 110.15(16) . . ? N1E C1E C2E 120.25(19) . . ? N1E C1E H1E 119.9 . . ? C2E C1E H1E 119.9 . . ? C1E C2E C3E 119.4(2) . . ? C1E C2E H2E 120.3 . . ? C3E C2E H2E 120.3 . . ? C4E C3E C2E 119.4(2) . . ? C4E C3E H3E 120.3 . . ? C2E C3E H3E 120.3 . . ? C5E C4E C3E 119.0(2) . . ? C5E C4E H4E 120.5 . . ? C3E C4E H4E 120.5 . . ? N1E C5E C4E 120.83(19) . . ? N1E C5E H5E 119.6 . . ? C4E C5E H5E 119.6 . . ? C7E C6E N1E 113.40(16) . . ? C7E C6E H6E1 108.9 . . ? N1E C6E H6E1 108.9 . . ? C7E C6E H6E2 108.9 . . ? N1E C6E H6E2 108.9 . . ? H6E1 C6E H6E2 107.7 . . ? C6E C7E S2E 119.53(15) . . ? C6E C7E S1E 119.06(15) . . ? S2E C7E S1E 120.89(12) . . ? F3E C8E F1E 107.86(18) . . ? F3E C8E F2E 107.96(17) . . ? F1E C8E F2E 107.86(18) . . ? F3E C8E S1E 112.13(15) . . ? F1E C8E S1E 111.12(15) . . ? F2E C8E S1E 109.75(15) . . ? F6E C9E F5E 108.20(17) . . ? F6E C9E F4E 107.75(17) . . ? F5E C9E F4E 107.87(16) . . ? F6E C9E S2E 111.99(14) . . ? F5E C9E S2E 110.99(14) . . ? F4E C9E S2E 109.90(14) . . ? C1 N1 C5 120.68(19) . . ? C1 N1 C6 119.46(18) . . ? C5 N1 C6 119.86(18) . . ? C5B N1B C1B 120.93(19) . . ? C5B N1B C6B 122.13(17) . . ? C1B N1B C6B 116.82(17) . . ? C1C N1C C5C 120.86(19) . . ? C1C N1C C6C 122.58(17) . . ? C5C N1C C6C 116.51(16) . . ? C5D N1D C1D 120.99(19) . . ? C5D N1D C6D 119.35(18) . . ? C1D N1D C6D 119.63(17) . . ? C5E N1E C1E 121.01(19) . . ? C5E N1E C6E 119.81(17) . . ? C1E N1E C6E 119.13(17) . . ? O4 S1 O3 120.34(9) . . ? O4 S1 C7 114.91(10) . . ? O3 S1 C7 107.81(10) . . ? O4 S1 C8 103.19(9) . . ? O3 S1 C8 102.40(10) . . ? C7 S1 C8 106.41(10) . . ? O2 S2 O1 120.26(9) . . ? O2 S2 C7 112.95(9) . . ? O1 S2 C7 110.00(10) . . ? O2 S2 C9 103.76(9) . . ? O1 S2 C9 101.99(10) . . ? C7 S2 C9 106.07(10) . . ? O2B S1B O1B 119.98(9) . . ? O2B S1B C7B 108.91(10) . . ? O1B S1B C7B 113.28(9) . . ? O2B S1B C8B 102.26(10) . . ? O1B S1B C8B 103.53(10) . . ? C7B S1B C8B 107.43(10) . . ? O3B S2B O4B 120.32(9) . . ? O3B S2B C7B 113.70(9) . . ? O4B S2B C7B 109.13(9) . . ? O3B S2B C9B 102.87(9) . . ? O4B S2B C9B 102.46(9) . . ? C7B S2B C9B 106.62(10) . . ? O2C S1C O1C 119.98(9) . . ? O2C S1C C7C 113.68(9) . . ? O1C S1C C7C 108.64(10) . . ? O2C S1C C8C 102.90(9) . . ? O1C S1C C8C 102.68(9) . . ? C7C S1C C8C 107.49(10) . . ? O4C S2C O3C 120.73(9) . . ? O4C S2C C7C 113.26(9) . . ? O3C S2C C7C 108.96(9) . . ? O4C S2C C9C 102.70(9) . . ? O3C S2C C9C 102.86(9) . . ? C7C S2C C9C 106.68(10) . . ? O1D S1D O2D 120.73(10) . . ? O1D S1D C7D 114.47(10) . . ? O2D S1D C7D 108.07(10) . . ? O1D S1D C8D 102.58(10) . . ? O2D S1D C8D 102.62(10) . . ? C7D S1D C8D 106.59(10) . . ? O4D S2D O3D 120.18(9) . . ? O4D S2D C7D 113.31(9) . . ? O3D S2D C7D 109.91(10) . . ? O4D S2D C9D 102.94(10) . . ? O3D S2D C9D 102.20(10) . . ? C7D S2D C9D 106.48(10) . . ? O1E S1E O2E 120.95(9) . . ? O1E S1E C7E 108.50(10) . . ? O2E S1E C7E 113.57(10) . . ? O1E S1E C8E 102.32(10) . . ? O2E S1E C8E 102.81(10) . . ? C7E S1E C8E 107.02(10) . . ? O4E S2E O3E 120.05(8) . . ? O4E S2E C7E 113.65(9) . . ? O3E S2E C7E 108.71(9) . . ? O4E S2E C9E 103.23(9) . . ? O3E S2E C9E 102.31(9) . . ? C7E S2E C9E 107.35(10) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.417 _refine_diff_density_min -0.421 _refine_diff_density_rms 0.059 _database_code_depnum_ccdc_archive 'CCDC 948820' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_CBA09-2b #============================================================================== # 2b #============================================================================== _audit_creation_date '31 August 2012' _audit_creation_method SHELXL-97 #============================================================================== # CHEMICAL DATA #============================================================================== _chemical_name_systematic ; 2-(2-Methylpyridin-1-ium-1-yl)-1,1-bis((trifluoromethyl)sulfonyl)ethan-1-ide ; _chemical_name_common ? _chemical_melting_point 459 _chemical_formula_moiety 'C10 H9 F6 N O4 S2' _chemical_formula_sum 'C10 H9 F6 N O4 S2' _chemical_formula_weight 385.30 _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_absolute_configuration . 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #============================================================================== # CRYSTAL DATA #============================================================================== _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 12.9290(14) _cell_length_b 10.0352(11) _cell_length_c 12.0294(13) _cell_angle_alpha 90.00 _cell_angle_beta 115.3760(10) _cell_angle_gamma 90.00 _cell_volume 1410.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 90 _cell_measurement_reflns_used 3160 _cell_measurement_theta_min 2.68 _cell_measurement_theta_max 27.57 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.815 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 776 _exptl_absorpt_coefficient_mu 0.466 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.9125 _exptl_absorpt_correction_T_max 0.9593 _exptl_absorpt_process_details ; Crystal Faces plugin in Bruker APEX2 software ; _exptl_special_details ; ? ; #============================================================================== # EXPERIMENTAL DATA #============================================================================== _diffrn_ambient_temperature 90 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker TXS fine-focus rotating anode' _diffrn_radiation_monochromator 'Bruker Helios multilayer confocal mirror' _diffrn_measurement_device_type 'Bruker APEXII CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.333 _diffrn_reflns_number 6577 _diffrn_reflns_av_R_equivalents 0.0215 _diffrn_reflns_av_sigmaI/netI 0.0256 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.68 _diffrn_reflns_theta_max 25.03 _reflns_number_total 2484 _reflns_number_gt 2219 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2006)' _computing_cell_refinement 'APEX2 (Bruker AXS, 2006)' _computing_data_reduction 'SAINT (Bruker AXS, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSHEL (Bruker AXS,2002)' _computing_publication_material 'XCIF (Bruker AXS, 2001)' _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^)+(0.0350P)^2^+0.8555P] 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 2484 _refine_ls_number_parameters 209 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0312 _refine_ls_R_factor_gt 0.0275 _refine_ls_wR_factor_ref 0.0725 _refine_ls_wR_factor_gt 0.0701 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.18055(15) 1.13661(18) -0.17128(17) 0.0155(4) Uani 1 1 d . . . C2 C 0.15369(16) 1.26800(19) -0.15844(18) 0.0180(4) Uani 1 1 d . . . H2 H 0.0935 1.3112 -0.2252 0.022 Uiso 1 1 calc R . . C3 C 0.21293(16) 1.33663(19) -0.05038(18) 0.0198(4) Uani 1 1 d . . . H3 H 0.1933 1.4261 -0.0422 0.024 Uiso 1 1 calc R . . C4 C 0.30169(16) 1.27357(19) 0.04645(18) 0.0208(4) Uani 1 1 d . . . H4 H 0.3437 1.3191 0.1218 0.025 Uiso 1 1 calc R . . C5 C 0.32741(16) 1.14423(18) 0.03107(17) 0.0176(4) Uani 1 1 d . . . H5 H 0.3889 1.1007 0.0962 0.021 Uiso 1 1 calc R . . C6 C 0.30208(15) 0.93344(17) -0.08029(16) 0.0150(4) Uani 1 1 d . . . H6A H 0.2473 0.8931 -0.1585 0.018 Uiso 1 1 calc R . . H6B H 0.3788 0.9323 -0.0800 0.018 Uiso 1 1 calc R . . C7 C 0.30525(15) 0.85084(17) 0.02478(16) 0.0133(4) Uani 1 1 d . . . C8 C 0.47276(15) 0.64525(18) 0.08766(16) 0.0164(4) Uani 1 1 d . . . C9 C 0.14789(17) 0.8960(2) 0.13026(19) 0.0232(4) Uani 1 1 d . . . F1 F 0.47150(11) 0.65896(12) -0.02236(10) 0.0294(3) Uani 1 1 d . . . F2 F 0.57832(9) 0.61132(11) 0.16752(10) 0.0264(3) Uani 1 1 d . . . F3 F 0.40259(10) 0.54712(11) 0.08243(12) 0.0302(3) Uani 1 1 d . . . F4 F 0.14930(11) 1.02499(12) 0.10626(12) 0.0347(3) Uani 1 1 d . . . F5 F 0.04335(10) 0.86534(14) 0.11780(13) 0.0390(3) Uani 1 1 d . . . F6 F 0.22031(11) 0.87495(15) 0.24643(11) 0.0384(3) Uani 1 1 d . . . N1 N 0.26729(12) 1.07725(14) -0.07470(14) 0.0136(3) Uani 1 1 d . . . O1 O 0.51961(11) 0.89208(13) 0.14300(12) 0.0206(3) Uani 1 1 d . . . O2 O 0.42171(11) 0.76197(14) 0.24685(11) 0.0208(3) Uani 1 1 d . . . O3 O 0.09090(11) 0.83079(14) -0.09550(12) 0.0241(3) Uani 1 1 d . . . O4 O 0.18610(12) 0.66160(14) 0.06750(14) 0.0265(3) Uani 1 1 d . . . C10 C 0.11567(18) 1.0618(2) -0.28836(18) 0.0260(5) Uani 1 1 d . . . H10A H 0.1686 1.0319 -0.3220 0.039 Uiso 1 1 calc R . . H10B H 0.0575 1.1202 -0.3479 0.039 Uiso 1 1 calc R . . H10C H 0.0783 0.9843 -0.2718 0.039 Uiso 1 1 calc R . . S1 S 0.43088(4) 0.80147(4) 0.13710(4) 0.01353(13) Uani 1 1 d . . . S2 S 0.18111(4) 0.79436(4) 0.02129(4) 0.01677(13) 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 C1 0.0154(9) 0.0175(9) 0.0150(9) 0.0033(7) 0.0078(8) 0.0003(7) C2 0.0149(9) 0.0177(10) 0.0198(10) 0.0038(8) 0.0058(8) 0.0025(7) C3 0.0207(10) 0.0130(9) 0.0249(10) -0.0002(8) 0.0088(8) -0.0001(7) C4 0.0210(10) 0.0154(10) 0.0204(10) -0.0025(8) 0.0034(8) -0.0035(8) C5 0.0148(9) 0.0163(10) 0.0167(9) 0.0033(7) 0.0018(8) -0.0015(7) C6 0.0176(9) 0.0113(9) 0.0170(9) 0.0015(7) 0.0082(8) 0.0025(7) C7 0.0133(9) 0.0109(9) 0.0156(9) 0.0011(7) 0.0061(8) 0.0008(7) C8 0.0179(9) 0.0163(9) 0.0141(9) 0.0015(7) 0.0059(8) 0.0037(7) C9 0.0195(10) 0.0274(11) 0.0269(11) 0.0040(9) 0.0139(9) 0.0018(8) F1 0.0423(7) 0.0321(7) 0.0186(6) 0.0036(5) 0.0176(6) 0.0143(6) F2 0.0221(6) 0.0272(6) 0.0249(6) 0.0020(5) 0.0053(5) 0.0120(5) F3 0.0327(7) 0.0126(6) 0.0489(8) -0.0035(5) 0.0209(6) -0.0018(5) F4 0.0455(8) 0.0233(7) 0.0488(8) -0.0017(6) 0.0329(7) 0.0052(6) F5 0.0247(7) 0.0512(9) 0.0524(9) 0.0053(7) 0.0273(6) 0.0014(6) F6 0.0348(7) 0.0601(9) 0.0228(7) 0.0027(6) 0.0146(6) 0.0172(6) N1 0.0141(7) 0.0111(7) 0.0169(8) 0.0018(6) 0.0079(6) 0.0008(6) O1 0.0151(7) 0.0159(7) 0.0274(8) 0.0003(6) 0.0058(6) -0.0015(5) O2 0.0236(7) 0.0254(7) 0.0132(6) 0.0010(6) 0.0077(6) 0.0048(6) O3 0.0151(7) 0.0289(8) 0.0228(7) 0.0006(6) 0.0028(6) -0.0036(6) O4 0.0260(8) 0.0171(7) 0.0384(9) 0.0060(6) 0.0158(7) -0.0033(6) C10 0.0328(12) 0.0208(10) 0.0165(10) -0.0007(8) 0.0028(9) 0.0071(9) S1 0.0138(2) 0.0121(2) 0.0133(2) -0.00051(17) 0.00449(18) 0.00106(17) S2 0.0143(2) 0.0151(2) 0.0202(3) 0.00108(18) 0.0067(2) -0.00226(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.358(2) . ? C1 C2 1.389(3) . ? C1 C10 1.496(3) . ? C2 C3 1.377(3) . ? C2 H2 0.9500 . ? C3 C4 1.389(3) . ? C3 H3 0.9500 . ? C4 C5 1.372(3) . ? C4 H4 0.9500 . ? C5 N1 1.352(2) . ? C5 H5 0.9500 . ? C6 C7 1.497(2) . ? C6 N1 1.522(2) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 S1 1.6817(17) . ? C7 S2 1.6856(17) . ? C8 F3 1.322(2) . ? C8 F1 1.324(2) . ? C8 F2 1.333(2) . ? C8 S1 1.8387(19) . ? C9 F6 1.324(2) . ? C9 F4 1.328(2) . ? C9 F5 1.331(2) . ? C9 S2 1.851(2) . ? O1 S1 1.4415(13) . ? O2 S1 1.4313(13) . ? O3 S2 1.4365(14) . ? O4 S2 1.4342(14) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? 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 C1 C2 118.38(17) . . ? N1 C1 C10 120.62(16) . . ? C2 C1 C10 121.00(17) . . ? C3 C2 C1 121.01(18) . . ? C3 C2 H2 119.5 . . ? C1 C2 H2 119.5 . . ? C2 C3 C4 119.29(18) . . ? C2 C3 H3 120.4 . . ? C4 C3 H3 120.4 . . ? C5 C4 C3 118.61(18) . . ? C5 C4 H4 120.7 . . ? C3 C4 H4 120.7 . . ? N1 C5 C4 121.50(17) . . ? N1 C5 H5 119.2 . . ? C4 C5 H5 119.2 . . ? C7 C6 N1 112.92(14) . . ? C7 C6 H6A 109.0 . . ? N1 C6 H6A 109.0 . . ? C7 C6 H6B 109.0 . . ? N1 C6 H6B 109.0 . . ? H6A C6 H6B 107.8 . . ? C6 C7 S1 120.59(13) . . ? C6 C7 S2 118.94(13) . . ? S1 C7 S2 120.16(10) . . ? F3 C8 F1 108.40(15) . . ? F3 C8 F2 108.29(15) . . ? F1 C8 F2 108.49(15) . . ? F3 C8 S1 111.05(12) . . ? F1 C8 S1 110.83(12) . . ? F2 C8 S1 109.70(12) . . ? F6 C9 F4 108.40(17) . . ? F6 C9 F5 107.86(16) . . ? F4 C9 F5 107.99(16) . . ? F6 C9 S2 112.69(14) . . ? F4 C9 S2 110.75(13) . . ? F5 C9 S2 109.00(14) . . ? C5 N1 C1 121.19(15) . . ? C5 N1 C6 116.84(14) . . ? C1 N1 C6 121.96(15) . . ? C1 C10 H10A 109.5 . . ? C1 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C1 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? O2 S1 O1 120.53(8) . . ? O2 S1 C7 112.92(8) . . ? O1 S1 C7 109.15(8) . . ? O2 S1 C8 102.39(8) . . ? O1 S1 C8 102.43(8) . . ? C7 S1 C8 107.95(9) . . ? O4 S2 O3 119.88(9) . . ? O4 S2 C7 114.74(9) . . ? O3 S2 C7 107.71(8) . . ? O4 S2 C9 102.89(9) . . ? O3 S2 C9 102.40(9) . . ? C7 S2 C9 107.73(9) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.401 _refine_diff_density_min -0.358 _refine_diff_density_rms 0.051 _database_code_depnum_ccdc_archive 'CCDC 948821' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_CBA09-2c #============================================================================== # 2c #============================================================================== _audit_creation_date '5 December 2012' _audit_creation_method SHELXL-97 #============================================================================== # CHEMICAL DATA #============================================================================== _chemical_name_systematic ; 2-(2-Ethylpyridin-1-ium-1-yl)-1,1-bis((trifluoromethyl)sulfonyl)ethan-1-ide ; _chemical_name_common ? _chemical_melting_point 429 _chemical_formula_moiety 'C11 H11 F6 N O4 S2' _chemical_formula_sum 'C11 H11 F6 N O4 S2' _chemical_formula_weight 399.33 _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_absolute_configuration . 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' 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' S S 0.1246 0.1234 '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' #============================================================================== # CRYSTAL DATA #============================================================================== _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 12.8277(11) _cell_length_b 10.1124(8) _cell_length_c 12.5805(10) _cell_angle_alpha 90.00 _cell_angle_beta 116.3960(10) _cell_angle_gamma 90.00 _cell_volume 1461.8(2) _cell_formula_units_Z 4 _cell_measurement_temperature 90 _cell_measurement_reflns_used 5670 _cell_measurement_theta_min 2.68 _cell_measurement_theta_max 27.64 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.814 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 808 _exptl_absorpt_coefficient_mu 0.453 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.8798 _exptl_absorpt_correction_T_max 0.8990 _exptl_absorpt_process_details ; Crystal Faces plugin in Bruker APEX2 software ; _exptl_special_details ; ? ; #============================================================================== # EXPERIMENTAL DATA #============================================================================== _diffrn_ambient_temperature 90 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker TXS fine-focus rotating anode' _diffrn_radiation_monochromator 'Bruker Helios multilayer confocal mirror' _diffrn_measurement_device_type 'Bruker APEXII CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.333 _diffrn_reflns_number 8329 _diffrn_reflns_av_R_equivalents 0.0150 _diffrn_reflns_av_sigmaI/netI 0.0176 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.68 _diffrn_reflns_theta_max 27.64 _reflns_number_total 3381 _reflns_number_gt 3136 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2006)' _computing_cell_refinement 'APEX2 (Bruker AXS, 2006)' _computing_data_reduction 'SAINT (Bruker AXS, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSHEL (Bruker AXS,2002)' _computing_publication_material 'XCIF (Bruker AXS, 2001)' _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^)+(0.0397P)^2^+0.8176P] 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 3381 _refine_ls_number_parameters 218 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0278 _refine_ls_R_factor_gt 0.0260 _refine_ls_wR_factor_ref 0.0723 _refine_ls_wR_factor_gt 0.0709 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _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 S1 S 0.68244(3) 0.78622(3) 0.02476(3) 0.01171(8) Uani 1 1 d . . . F1 F 0.63756(9) 1.01226(9) 0.10032(9) 0.0298(2) Uani 1 1 d . . . O1 O 0.58778(8) 0.81538(10) -0.08925(8) 0.0180(2) Uani 1 1 d . . . C1 C 0.82170(11) 1.13696(13) 0.03996(11) 0.0139(2) Uani 1 1 d . . . H1 H 0.8726 1.0880 0.1077 0.017 Uiso 1 1 calc R . . N1 N 0.77230(9) 1.07645(10) -0.06716(9) 0.0102(2) Uani 1 1 d . . . S2 S 0.93573(3) 0.80222(3) 0.13718(3) 0.01067(8) Uani 1 1 d . . . F2 F 0.53898(8) 0.84525(10) 0.11294(9) 0.0295(2) Uani 1 1 d . . . O2 O 0.69583(8) 0.65501(10) 0.07279(9) 0.0185(2) Uani 1 1 d . . . C2 C 0.79991(11) 1.26737(13) 0.05306(12) 0.0153(3) Uani 1 1 d . . . H2 H 0.8356 1.3086 0.1287 0.018 Uiso 1 1 calc R . . F3 F 0.71866(9) 0.86813(12) 0.23931(8) 0.0340(2) Uani 1 1 d . . . O3 O 1.02408(8) 0.89362(9) 0.14175(9) 0.0175(2) Uani 1 1 d . . . C3 C 0.72459(11) 1.33803(13) -0.04643(12) 0.0155(3) Uani 1 1 d . . . H3 H 0.7058 1.4274 -0.0393 0.019 Uiso 1 1 calc R . . F4 F 0.97404(9) 0.66365(10) -0.01815(8) 0.0286(2) Uani 1 1 d . . . O4 O 0.93007(8) 0.76330(10) 0.24402(8) 0.0174(2) Uani 1 1 d . . . C4 C 0.67761(11) 1.27611(13) -0.15569(12) 0.0143(2) Uani 1 1 d . . . H4 H 0.6270 1.3241 -0.2242 0.017 Uiso 1 1 calc R . . C5 C 0.70320(10) 1.14467(12) -0.16699(11) 0.0114(2) Uani 1 1 d . . . F5 F 1.08664(7) 0.61603(9) 0.16484(8) 0.02256(19) Uani 1 1 d . . . C6 C 0.80017(11) 0.93071(12) -0.07311(11) 0.0113(2) Uani 1 1 d . . . H6A H 0.7400 0.8926 -0.1476 0.014 Uiso 1 1 calc R . . H6B H 0.8758 0.9242 -0.0761 0.014 Uiso 1 1 calc R . . F6 F 0.90923(8) 0.54848(8) 0.08361(9) 0.0275(2) Uani 1 1 d . . . C9 C 0.97783(11) 0.64798(13) 0.08819(11) 0.0145(2) Uani 1 1 d . . . C8 C 0.80592(10) 0.85019(12) 0.02910(11) 0.0108(2) Uani 1 1 d . . . C11 C 0.65563(11) 1.08170(13) -0.28779(11) 0.0146(2) Uani 1 1 d . . . H11A H 0.7143 1.0196 -0.2900 0.018 Uiso 1 1 calc R . . H11B H 0.6423 1.1513 -0.3478 0.018 Uiso 1 1 calc R . . C12 C 0.54152(12) 1.00665(14) -0.32089(12) 0.0170(3) Uani 1 1 d . . . H12A H 0.4832 1.0672 -0.3180 0.025 Uiso 1 1 calc R . . H12B H 0.5550 0.9341 -0.2646 0.025 Uiso 1 1 calc R . . H12C H 0.5134 0.9707 -0.4013 0.025 Uiso 1 1 calc R . . C10 C 0.64344(12) 0.88397(15) 0.12633(13) 0.0193(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 0.01053(15) 0.01114(15) 0.01353(15) 0.00146(11) 0.00542(12) -0.00071(10) F1 0.0361(5) 0.0188(4) 0.0457(6) -0.0039(4) 0.0284(5) 0.0025(4) O1 0.0118(4) 0.0220(5) 0.0167(5) 0.0027(4) 0.0032(4) -0.0016(4) C1 0.0120(6) 0.0132(6) 0.0137(6) -0.0006(5) 0.0033(5) -0.0013(5) N1 0.0104(5) 0.0087(5) 0.0123(5) 0.0003(4) 0.0057(4) -0.0007(4) S2 0.01015(15) 0.01023(15) 0.01047(14) -0.00019(10) 0.00353(11) 0.00044(10) F2 0.0217(4) 0.0363(5) 0.0408(5) 0.0011(4) 0.0232(4) -0.0001(4) O2 0.0186(5) 0.0139(5) 0.0244(5) 0.0057(4) 0.0110(4) -0.0006(4) C2 0.0134(6) 0.0138(6) 0.0158(6) -0.0040(5) 0.0038(5) -0.0019(5) F3 0.0308(5) 0.0549(7) 0.0180(4) -0.0038(4) 0.0123(4) 0.0099(5) O3 0.0118(4) 0.0150(5) 0.0222(5) 0.0001(4) 0.0044(4) -0.0029(4) C3 0.0130(6) 0.0102(6) 0.0224(6) -0.0012(5) 0.0071(5) 0.0001(5) F4 0.0396(5) 0.0321(5) 0.0187(4) 0.0014(4) 0.0172(4) 0.0143(4) O4 0.0176(5) 0.0231(5) 0.0107(4) 0.0020(4) 0.0057(4) 0.0033(4) C4 0.0126(6) 0.0127(6) 0.0168(6) 0.0032(5) 0.0057(5) 0.0021(5) C5 0.0104(5) 0.0130(6) 0.0119(5) 0.0008(4) 0.0059(4) -0.0011(4) F5 0.0149(4) 0.0233(4) 0.0255(4) 0.0022(3) 0.0053(3) 0.0082(3) C6 0.0139(6) 0.0079(5) 0.0126(5) 0.0007(4) 0.0062(5) 0.0012(4) F6 0.0238(4) 0.0119(4) 0.0493(6) -0.0054(4) 0.0184(4) -0.0020(3) C9 0.0138(6) 0.0138(6) 0.0155(6) 0.0001(5) 0.0062(5) 0.0024(5) C8 0.0099(5) 0.0102(5) 0.0120(5) 0.0016(4) 0.0045(4) 0.0003(4) C11 0.0176(6) 0.0149(6) 0.0111(5) 0.0006(5) 0.0063(5) 0.0006(5) C12 0.0163(6) 0.0181(6) 0.0136(6) -0.0005(5) 0.0041(5) -0.0008(5) C10 0.0180(6) 0.0222(7) 0.0216(7) 0.0006(5) 0.0122(5) 0.0017(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 S1 O1 1.4387(10) . ? S1 O2 1.4363(10) . ? S1 C8 1.6892(12) . ? S1 C10 1.8516(14) . ? F1 C10 1.3319(17) . ? C1 N1 1.3538(16) . ? C1 C2 1.3732(18) . ? C1 H1 0.9500 . ? N1 C5 1.3598(16) . ? N1 C6 1.5262(15) . ? S2 O4 1.4330(9) . ? S2 O3 1.4437(10) . ? S2 C8 1.6863(12) . ? S2 C9 1.8440(13) . ? F2 C10 1.3328(16) . ? C2 C3 1.3912(19) . ? C2 H2 0.9500 . ? F3 C10 1.3257(17) . ? C3 C4 1.3814(19) . ? C3 H3 0.9500 . ? F4 C9 1.3265(15) . ? C4 C5 1.3915(18) . ? C4 H4 0.9500 . ? C5 C11 1.5043(17) . ? F5 C9 1.3364(15) . ? C6 C8 1.4958(16) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? F6 C9 1.3210(16) . ? C11 C12 1.5330(18) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? 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 119.92(6) . . ? O1 S1 C8 108.51(6) . . ? O2 S1 C8 113.90(6) . . ? O1 S1 C10 102.20(6) . . ? O2 S1 C10 102.78(6) . . ? C8 S1 C10 108.09(6) . . ? N1 C1 C2 121.56(12) . . ? N1 C1 H1 119.2 . . ? C2 C1 H1 119.2 . . ? C1 N1 C5 120.97(11) . . ? C1 N1 C6 117.98(10) . . ? C5 N1 C6 121.02(10) . . ? O4 S2 O3 120.32(6) . . ? O4 S2 C8 113.06(6) . . ? O3 S2 C8 108.92(6) . . ? O4 S2 C9 103.04(6) . . ? O3 S2 C9 102.32(6) . . ? C8 S2 C9 107.74(6) . . ? C1 C2 C3 118.83(12) . . ? C1 C2 H2 120.6 . . ? C3 C2 H2 120.6 . . ? C4 C3 C2 118.93(12) . . ? C4 C3 H3 120.5 . . ? C2 C3 H3 120.5 . . ? C3 C4 C5 121.08(12) . . ? C3 C4 H4 119.5 . . ? C5 C4 H4 119.5 . . ? N1 C5 C4 118.48(11) . . ? N1 C5 C11 121.56(11) . . ? C4 C5 C11 119.96(11) . . ? C8 C6 N1 113.99(10) . . ? C8 C6 H6A 108.8 . . ? N1 C6 H6A 108.8 . . ? C8 C6 H6B 108.8 . . ? N1 C6 H6B 108.8 . . ? H6A C6 H6B 107.6 . . ? F6 C9 F4 108.78(11) . . ? F6 C9 F5 108.00(11) . . ? F4 C9 F5 108.35(11) . . ? F6 C9 S2 111.75(9) . . ? F4 C9 S2 110.56(9) . . ? F5 C9 S2 109.30(9) . . ? C6 C8 S1 119.57(9) . . ? C6 C8 S2 120.23(9) . . ? S1 C8 S2 119.44(7) . . ? C5 C11 C12 113.17(10) . . ? C5 C11 H11A 108.9 . . ? C12 C11 H11A 108.9 . . ? C5 C11 H11B 108.9 . . ? C12 C11 H11B 108.9 . . ? H11A C11 H11B 107.8 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? F3 C10 F1 108.41(12) . . ? F3 C10 F2 108.16(12) . . ? F1 C10 F2 108.13(12) . . ? F3 C10 S1 112.60(10) . . ? F1 C10 S1 110.71(9) . . ? F2 C10 S1 108.72(10) . . ? 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 C1 N1 C5 3.07(19) . . . . ? C2 C1 N1 C6 -179.18(11) . . . . ? N1 C1 C2 C3 0.42(19) . . . . ? C1 C2 C3 C4 -2.34(19) . . . . ? C2 C3 C4 C5 0.91(19) . . . . ? C1 N1 C5 C4 -4.44(17) . . . . ? C6 N1 C5 C4 177.87(11) . . . . ? C1 N1 C5 C11 174.96(11) . . . . ? C6 N1 C5 C11 -2.73(17) . . . . ? C3 C4 C5 N1 2.46(19) . . . . ? C3 C4 C5 C11 -176.95(12) . . . . ? C1 N1 C6 C8 39.48(15) . . . . ? C5 N1 C6 C8 -142.77(11) . . . . ? O4 S2 C9 F6 51.57(10) . . . . ? O3 S2 C9 F6 177.09(9) . . . . ? C8 S2 C9 F6 -68.18(11) . . . . ? O4 S2 C9 F4 172.89(9) . . . . ? O3 S2 C9 F4 -61.59(10) . . . . ? C8 S2 C9 F4 53.14(11) . . . . ? O4 S2 C9 F5 -67.92(10) . . . . ? O3 S2 C9 F5 57.60(10) . . . . ? C8 S2 C9 F5 172.33(9) . . . . ? N1 C6 C8 S1 85.23(12) . . . . ? N1 C6 C8 S2 -104.86(11) . . . . ? O1 S1 C8 C6 4.37(12) . . . . ? O2 S1 C8 C6 140.73(10) . . . . ? C10 S1 C8 C6 -105.74(10) . . . . ? O1 S1 C8 S2 -165.62(7) . . . . ? O2 S1 C8 S2 -29.26(10) . . . . ? C10 S1 C8 S2 84.27(9) . . . . ? O4 S2 C8 C6 161.73(9) . . . . ? O3 S2 C8 C6 25.18(12) . . . . ? C9 S2 C8 C6 -85.09(11) . . . . ? O4 S2 C8 S1 -28.35(10) . . . . ? O3 S2 C8 S1 -164.89(7) . . . . ? C9 S2 C8 S1 84.83(9) . . . . ? N1 C5 C11 C12 86.00(14) . . . . ? C4 C5 C11 C12 -94.61(14) . . . . ? O1 S1 C10 F3 177.93(10) . . . . ? O2 S1 C10 F3 53.02(12) . . . . ? C8 S1 C10 F3 -67.72(12) . . . . ? O1 S1 C10 F1 -60.53(11) . . . . ? O2 S1 C10 F1 174.55(10) . . . . ? C8 S1 C10 F1 53.82(11) . . . . ? O1 S1 C10 F2 58.11(11) . . . . ? O2 S1 C10 F2 -66.81(11) . . . . ? C8 S1 C10 F2 172.45(9) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.64 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.526 _refine_diff_density_min -0.344 _refine_diff_density_rms 0.054 _database_code_depnum_ccdc_archive 'CCDC 948822' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_CBA09-2d #============================================================================== # 2d #============================================================================== _audit_creation_date '25 January 2013' _audit_creation_method SHELXL-97 #============================================================================== # CHEMICAL DATA #============================================================================== _chemical_name_systematic ; 2-(2-Isobutylpyridin-1-ium-1-yl)-1,1-bis((trifluoromethyl)sulfonyl)ethan-1-ide ; _chemical_name_common ? _chemical_melting_point 448 _chemical_formula_moiety 'C13 H15 F6 N O4 S2' _chemical_formula_sum 'C13 H15 F6 N O4 S2' _chemical_formula_weight 427.38 _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_absolute_configuration . 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #============================================================================== # CRYSTAL DATA #============================================================================== _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.7218(8) _cell_length_b 11.6643(11) _cell_length_c 16.8924(15) _cell_angle_alpha 90.00 _cell_angle_beta 91.9270(10) _cell_angle_gamma 90.00 _cell_volume 1717.6(3) _cell_formula_units_Z 4 _cell_measurement_temperature 90 _cell_measurement_reflns_used 6266 _cell_measurement_theta_min 2.41 _cell_measurement_theta_max 27.61 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.653 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 872 _exptl_absorpt_coefficient_mu 0.392 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.8719 _exptl_absorpt_correction_T_max 0.9258 _exptl_absorpt_process_details ; Crystal Faces plugin in Bruker APEX2 software ; _exptl_special_details ; ? ; #============================================================================== # EXPERIMENTAL DATA #============================================================================== _diffrn_ambient_temperature 90 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker TXS fine-focus rotating anode' _diffrn_radiation_monochromator 'Bruker Helios multilayer confocal mirror' _diffrn_measurement_device_type 'Bruker APEXII CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.333 _diffrn_reflns_number 8174 _diffrn_reflns_av_R_equivalents 0.0172 _diffrn_reflns_av_sigmaI/netI 0.0180 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 25.03 _reflns_number_total 3033 _reflns_number_gt 2847 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2006)' _computing_cell_refinement 'APEX2 (Bruker AXS, 2006)' _computing_data_reduction 'SAINT (Bruker AXS, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSHEL (Bruker AXS,2002)' _computing_publication_material 'XCIF (Bruker AXS, 2001)' _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^)+(0.0320P)^2^+1.2705P] 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 3033 _refine_ls_number_parameters 238 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0275 _refine_ls_R_factor_gt 0.0260 _refine_ls_wR_factor_ref 0.0678 _refine_ls_wR_factor_gt 0.0667 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.75749(4) 0.45589(3) 0.12864(2) 0.01161(10) Uani 1 1 d . . . S2 S 0.89990(4) 0.23781(3) 0.08573(2) 0.01125(10) Uani 1 1 d . . . N1 N 0.55776(14) 0.28189(11) -0.02760(7) 0.0115(3) Uani 1 1 d . . . C3 C 0.28750(18) 0.16233(15) -0.04321(10) 0.0192(3) Uani 1 1 d . . . H3 H 0.1951 0.1195 -0.0486 0.023 Uiso 1 1 calc R . . C12 C 0.90858(18) 0.56091(14) 0.10636(9) 0.0156(3) Uani 1 1 d . . . C10 C 0.70297(17) 0.35274(13) -0.01653(9) 0.0126(3) Uani 1 1 d . . . H10A H 0.7782 0.3267 -0.0553 0.015 Uiso 1 1 calc R . . H10B H 0.6783 0.4339 -0.0285 0.015 Uiso 1 1 calc R . . C4 C 0.32709(18) 0.21615(14) 0.02791(10) 0.0168(3) Uani 1 1 d . . . H4 H 0.2616 0.2118 0.0716 0.020 Uiso 1 1 calc R . . C11 C 0.77605(17) 0.34608(13) 0.06485(9) 0.0117(3) Uani 1 1 d . . . C5 C 0.46228(17) 0.27553(14) 0.03383(9) 0.0142(3) Uani 1 1 d . . . H5 H 0.4898 0.3131 0.0821 0.017 Uiso 1 1 calc R . . C1 C 0.52069(18) 0.23311(13) -0.09898(9) 0.0135(3) Uani 1 1 d . . . C13 C 0.79722(19) 0.13203(14) 0.14536(10) 0.0199(4) Uani 1 1 d . . . C7 C 0.75691(18) 0.15765(14) -0.17125(9) 0.0173(3) Uani 1 1 d . . . H7 H 0.8280 0.1718 -0.1246 0.021 Uiso 1 1 calc R . . C6 C 0.62310(18) 0.24504(14) -0.16886(9) 0.0156(3) Uani 1 1 d . . . H6A H 0.6668 0.3234 -0.1685 0.019 Uiso 1 1 calc R . . H6B H 0.5592 0.2368 -0.2181 0.019 Uiso 1 1 calc R . . C2 C 0.38418(18) 0.17190(14) -0.10606(10) 0.0173(3) Uani 1 1 d . . . H2 H 0.3568 0.1360 -0.1550 0.021 Uiso 1 1 calc R . . C8 C 0.84523(19) 0.17693(17) -0.24701(10) 0.0234(4) Uani 1 1 d . . . H8A H 0.9362 0.1275 -0.2463 0.035 Uiso 1 1 calc R . . H8B H 0.8770 0.2574 -0.2499 0.035 Uiso 1 1 calc R . . H8C H 0.7790 0.1582 -0.2932 0.035 Uiso 1 1 calc R . . C9 C 0.6988(2) 0.03438(16) -0.16722(12) 0.0292(4) Uani 1 1 d . . . H9A H 0.6238 0.0208 -0.2107 0.044 Uiso 1 1 calc R . . H9B H 0.6501 0.0219 -0.1165 0.044 Uiso 1 1 calc R . . H9C H 0.7852 -0.0186 -0.1719 0.044 Uiso 1 1 calc R . . O4 O 1.02574(12) 0.26988(10) 0.13790(6) 0.0160(2) Uani 1 1 d . . . O2 O 0.79230(12) 0.42458(10) 0.20934(6) 0.0165(2) Uani 1 1 d . . . O3 O 0.92750(13) 0.17594(10) 0.01394(6) 0.0174(2) Uani 1 1 d . . . O1 O 0.61883(12) 0.51782(10) 0.10755(7) 0.0173(2) Uani 1 1 d . . . F1 F 0.89996(11) 0.58887(8) 0.02953(5) 0.0198(2) Uani 1 1 d . . . F2 F 1.04867(10) 0.51906(8) 0.12255(6) 0.0213(2) Uani 1 1 d . . . F3 F 0.89214(12) 0.65595(8) 0.14860(6) 0.0236(2) Uani 1 1 d . . . F5 F 0.88631(11) 0.04072(8) 0.15747(6) 0.0242(2) Uani 1 1 d . . . F6 F 0.66950(12) 0.09733(9) 0.10700(8) 0.0356(3) Uani 1 1 d . . . F4 F 0.76057(14) 0.17460(9) 0.21471(7) 0.0377(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 0.01212(19) 0.0122(2) 0.01064(19) -0.00060(14) 0.00177(14) -0.00088(14) S2 0.00984(19) 0.0134(2) 0.01049(19) 0.00021(14) 0.00057(14) 0.00011(14) N1 0.0102(6) 0.0124(6) 0.0118(6) 0.0008(5) -0.0005(5) 0.0015(5) C3 0.0118(7) 0.0207(9) 0.0250(9) -0.0028(7) -0.0009(6) -0.0013(6) C12 0.0188(8) 0.0150(8) 0.0131(8) -0.0017(6) 0.0020(6) -0.0023(6) C10 0.0123(7) 0.0138(8) 0.0117(7) 0.0003(6) 0.0004(6) -0.0023(6) C4 0.0120(7) 0.0205(9) 0.0180(8) -0.0004(7) 0.0034(6) 0.0014(6) C11 0.0118(7) 0.0120(8) 0.0112(7) -0.0003(6) -0.0001(6) -0.0004(6) C5 0.0132(7) 0.0170(8) 0.0124(7) -0.0001(6) 0.0004(6) 0.0029(6) C1 0.0141(7) 0.0131(8) 0.0130(7) 0.0008(6) -0.0028(6) 0.0048(6) C13 0.0181(8) 0.0151(8) 0.0269(9) 0.0035(7) 0.0038(7) 0.0006(7) C7 0.0152(8) 0.0243(9) 0.0122(7) -0.0014(6) -0.0008(6) 0.0035(7) C6 0.0163(8) 0.0200(8) 0.0104(7) -0.0003(6) -0.0014(6) 0.0018(6) C2 0.0153(8) 0.0189(8) 0.0173(8) -0.0044(6) -0.0032(6) 0.0018(6) C8 0.0178(8) 0.0362(11) 0.0162(8) -0.0014(7) 0.0021(7) 0.0045(7) C9 0.0289(10) 0.0239(10) 0.0353(11) -0.0004(8) 0.0089(8) 0.0071(8) O4 0.0125(5) 0.0203(6) 0.0149(5) 0.0001(4) -0.0020(4) 0.0005(4) O2 0.0212(6) 0.0183(6) 0.0101(5) -0.0005(4) 0.0021(4) -0.0008(5) O3 0.0185(6) 0.0190(6) 0.0145(6) -0.0031(5) -0.0001(4) 0.0048(5) O1 0.0159(6) 0.0156(6) 0.0203(6) -0.0009(5) 0.0013(4) 0.0023(4) F1 0.0263(5) 0.0180(5) 0.0155(5) 0.0032(4) 0.0054(4) -0.0018(4) F2 0.0142(5) 0.0236(5) 0.0261(5) 0.0011(4) 0.0001(4) -0.0039(4) F3 0.0310(5) 0.0161(5) 0.0241(5) -0.0081(4) 0.0064(4) -0.0064(4) F5 0.0252(5) 0.0169(5) 0.0306(6) 0.0085(4) 0.0005(4) 0.0047(4) F6 0.0182(5) 0.0219(6) 0.0662(8) 0.0146(5) -0.0067(5) -0.0069(4) F4 0.0579(8) 0.0235(6) 0.0337(6) 0.0056(5) 0.0313(6) 0.0005(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 S1 O2 1.4339(11) . ? S1 O1 1.4431(11) . ? S1 C11 1.6851(15) . ? S1 C12 1.8472(16) . ? S2 O4 1.4340(11) . ? S2 O3 1.4384(11) . ? S2 C11 1.6913(15) . ? S2 C13 1.8438(17) . ? N1 C5 1.3543(19) . ? N1 C1 1.362(2) . ? N1 C10 1.5186(19) . ? C3 C2 1.382(2) . ? C3 C4 1.389(2) . ? C3 H3 0.9500 . ? C12 F3 1.3287(18) . ? C12 F2 1.3356(18) . ? C12 F1 1.3377(18) . ? C10 C11 1.498(2) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C4 C5 1.368(2) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C1 C2 1.390(2) . ? C1 C6 1.511(2) . ? C13 F4 1.322(2) . ? C13 F5 1.3302(19) . ? C13 F6 1.333(2) . ? C7 C9 1.527(3) . ? C7 C8 1.532(2) . ? C7 C6 1.551(2) . ? C7 H7 1.0000 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C2 H2 0.9500 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? 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 120.74(7) . . ? O2 S1 C11 113.11(7) . . ? O1 S1 C11 108.68(7) . . ? O2 S1 C12 103.47(7) . . ? O1 S1 C12 102.44(7) . . ? C11 S1 C12 106.81(7) . . ? O4 S2 O3 120.18(7) . . ? O4 S2 C11 113.81(7) . . ? O3 S2 C11 108.83(7) . . ? O4 S2 C13 102.39(7) . . ? O3 S2 C13 102.89(7) . . ? C11 S2 C13 107.16(7) . . ? C5 N1 C1 121.44(13) . . ? C5 N1 C10 117.85(12) . . ? C1 N1 C10 120.56(12) . . ? C2 C3 C4 119.18(15) . . ? C2 C3 H3 120.4 . . ? C4 C3 H3 120.4 . . ? F3 C12 F2 108.03(12) . . ? F3 C12 F1 108.31(13) . . ? F2 C12 F1 108.00(12) . . ? F3 C12 S1 110.69(10) . . ? F2 C12 S1 111.70(11) . . ? F1 C12 S1 110.01(10) . . ? C11 C10 N1 114.35(12) . . ? C11 C10 H10A 108.7 . . ? N1 C10 H10A 108.7 . . ? C11 C10 H10B 108.7 . . ? N1 C10 H10B 108.7 . . ? H10A C10 H10B 107.6 . . ? C5 C4 C3 118.73(15) . . ? C5 C4 H4 120.6 . . ? C3 C4 H4 120.6 . . ? C10 C11 S1 120.03(11) . . ? C10 C11 S2 118.63(11) . . ? S1 C11 S2 120.57(9) . . ? N1 C5 C4 121.49(14) . . ? N1 C5 H5 119.3 . . ? C4 C5 H5 119.3 . . ? N1 C1 C2 117.89(14) . . ? N1 C1 C6 121.62(14) . . ? C2 C1 C6 120.49(14) . . ? F4 C13 F5 108.79(14) . . ? F4 C13 F6 108.78(14) . . ? F5 C13 F6 107.81(14) . . ? F4 C13 S2 111.67(12) . . ? F5 C13 S2 109.14(11) . . ? F6 C13 S2 110.55(12) . . ? C9 C7 C8 110.64(14) . . ? C9 C7 C6 111.50(13) . . ? C8 C7 C6 108.97(13) . . ? C9 C7 H7 108.6 . . ? C8 C7 H7 108.6 . . ? C6 C7 H7 108.6 . . ? C1 C6 C7 115.15(13) . . ? C1 C6 H6A 108.5 . . ? C7 C6 H6A 108.5 . . ? C1 C6 H6B 108.5 . . ? C7 C6 H6B 108.5 . . ? H6A C6 H6B 107.5 . . ? C3 C2 C1 121.22(15) . . ? C3 C2 H2 119.4 . . ? C1 C2 H2 119.4 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 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 O2 S1 C12 F3 -66.88(12) . . . . ? O1 S1 C12 F3 59.35(12) . . . . ? C11 S1 C12 F3 173.51(11) . . . . ? O2 S1 C12 F2 53.53(12) . . . . ? O1 S1 C12 F2 179.77(10) . . . . ? C11 S1 C12 F2 -66.08(12) . . . . ? O2 S1 C12 F1 173.46(10) . . . . ? O1 S1 C12 F1 -60.31(12) . . . . ? C11 S1 C12 F1 53.85(12) . . . . ? C5 N1 C10 C11 36.78(18) . . . . ? C1 N1 C10 C11 -147.56(13) . . . . ? C2 C3 C4 C5 -1.1(2) . . . . ? N1 C10 C11 S1 -103.82(14) . . . . ? N1 C10 C11 S2 86.12(14) . . . . ? O2 S1 C11 C10 162.48(11) . . . . ? O1 S1 C11 C10 25.51(14) . . . . ? C12 S1 C11 C10 -84.34(13) . . . . ? O2 S1 C11 S2 -27.66(12) . . . . ? O1 S1 C11 S2 -164.63(9) . . . . ? C12 S1 C11 S2 85.52(11) . . . . ? O4 S2 C11 C10 144.10(11) . . . . ? O3 S2 C11 C10 7.14(14) . . . . ? C13 S2 C11 C10 -103.46(12) . . . . ? O4 S2 C11 S1 -25.90(12) . . . . ? O3 S2 C11 S1 -162.86(9) . . . . ? C13 S2 C11 S1 86.54(11) . . . . ? C1 N1 C5 C4 2.5(2) . . . . ? C10 N1 C5 C4 178.14(14) . . . . ? C3 C4 C5 N1 -0.5(2) . . . . ? C5 N1 C1 C2 -2.8(2) . . . . ? C10 N1 C1 C2 -178.25(13) . . . . ? C5 N1 C1 C6 176.89(14) . . . . ? C10 N1 C1 C6 1.4(2) . . . . ? O4 S2 C13 F4 55.12(13) . . . . ? O3 S2 C13 F4 -179.56(12) . . . . ? C11 S2 C13 F4 -64.91(14) . . . . ? O4 S2 C13 F5 -65.20(13) . . . . ? O3 S2 C13 F5 60.13(13) . . . . ? C11 S2 C13 F5 174.78(11) . . . . ? O4 S2 C13 F6 176.38(11) . . . . ? O3 S2 C13 F6 -58.29(13) . . . . ? C11 S2 C13 F6 56.36(13) . . . . ? N1 C1 C6 C7 83.91(18) . . . . ? C2 C1 C6 C7 -96.45(17) . . . . ? C9 C7 C6 C1 54.98(18) . . . . ? C8 C7 C6 C1 177.40(13) . . . . ? C4 C3 C2 C1 0.8(2) . . . . ? N1 C1 C2 C3 1.1(2) . . . . ? C6 C1 C2 C3 -178.54(15) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.333 _refine_diff_density_min -0.384 _refine_diff_density_rms 0.051 _database_code_depnum_ccdc_archive 'CCDC 948823' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_CBA09-2e #============================================================================== # 2e #============================================================================== _audit_creation_date '10 January 2013' _audit_creation_method SHELXL-97 #============================================================================== # CHEMICAL DATA #============================================================================== _chemical_name_systematic ; 2-(2-Isopropylpyridin-1-ium-1-yl)-1,1-bis((trifluoromethyl)sulfonyl)ethan-1-ide ; _chemical_name_common ? _chemical_melting_point 458 _chemical_formula_moiety 'C12 H13 F6 N O4 S2' _chemical_formula_sum 'C12 H13 F6 N O4 S2' _chemical_formula_weight 413.35 _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_absolute_configuration . 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #============================================================================== # CRYSTAL DATA #============================================================================== _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.5646(8) _cell_length_b 12.1042(11) _cell_length_c 16.0084(14) _cell_angle_alpha 90.00 _cell_angle_beta 101.8640(10) _cell_angle_gamma 90.00 _cell_volume 1624.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 90 _cell_measurement_reflns_used 4335 _cell_measurement_theta_min 2.51 _cell_measurement_theta_max 27.47 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.691 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 840 _exptl_absorpt_coefficient_mu 0.411 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.9187 _exptl_absorpt_correction_T_max 0.9485 _exptl_absorpt_process_details ; Crystal Faces plugin in Bruker APEX2 software ; _exptl_special_details ; ? ; #============================================================================== # EXPERIMENTAL DATA #============================================================================== _diffrn_ambient_temperature 90 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker TXS fine-focus rotating anode' _diffrn_radiation_monochromator 'Bruker Helios multilayer confocal mirror' _diffrn_measurement_device_type 'Bruker APEXII CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.333 _diffrn_reflns_number 7745 _diffrn_reflns_av_R_equivalents 0.0219 _diffrn_reflns_av_sigmaI/netI 0.0250 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.13 _diffrn_reflns_theta_max 25.03 _reflns_number_total 2865 _reflns_number_gt 2610 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2006)' _computing_cell_refinement 'APEX2 (Bruker AXS, 2006)' _computing_data_reduction 'SAINT (Bruker AXS, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSHEL (Bruker AXS,2002)' _computing_publication_material 'XCIF (Bruker AXS, 2001)' _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^)+(0.0341P)^2^+0.8839P] 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 2865 _refine_ls_number_parameters 228 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0293 _refine_ls_R_factor_gt 0.0263 _refine_ls_wR_factor_ref 0.0698 _refine_ls_wR_factor_gt 0.0673 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _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 C1 C 0.38738(19) 0.31484(13) 0.80822(10) 0.0124(3) Uani 1 1 d . . . C2 C 0.5150(2) 0.26902(14) 0.77869(10) 0.0156(4) Uani 1 1 d . . . H2 H 0.5073 0.2603 0.7190 0.019 Uiso 1 1 calc R . . C3 C 0.6531(2) 0.23585(14) 0.83430(11) 0.0167(4) Uani 1 1 d . . . H3 H 0.7384 0.2038 0.8130 0.020 Uiso 1 1 calc R . . C4 C 0.6653(2) 0.24993(14) 0.92145(10) 0.0148(3) Uani 1 1 d . . . H4 H 0.7584 0.2273 0.9609 0.018 Uiso 1 1 calc R . . C5 C 0.54007(19) 0.29716(13) 0.94900(10) 0.0134(3) Uani 1 1 d . . . H5 H 0.5485 0.3091 1.0084 0.016 Uiso 1 1 calc R . . C6 C 0.23590(19) 0.35271(13) 0.74843(10) 0.0139(3) Uani 1 1 d . . . H6 H 0.1435 0.3323 0.7746 0.017 Uiso 1 1 calc R . . C7 C 0.2360(2) 0.47904(14) 0.73820(11) 0.0201(4) Uani 1 1 d . . . H7A H 0.2504 0.5139 0.7945 0.030 Uiso 1 1 calc R . . H7B H 0.1342 0.5028 0.7029 0.030 Uiso 1 1 calc R . . H7C H 0.3235 0.5009 0.7107 0.030 Uiso 1 1 calc R . . C8 C 0.2117(2) 0.29772(15) 0.66051(11) 0.0201(4) Uani 1 1 d . . . H8A H 0.2957 0.3221 0.6313 0.030 Uiso 1 1 calc R . . H8B H 0.1072 0.3186 0.6265 0.030 Uiso 1 1 calc R . . H8C H 0.2167 0.2173 0.6674 0.030 Uiso 1 1 calc R . . C9 C 0.27710(19) 0.38090(13) 0.93409(10) 0.0124(3) Uani 1 1 d . . . H9A H 0.3094 0.4578 0.9501 0.015 Uiso 1 1 calc R . . H9B H 0.1762 0.3839 0.8909 0.015 Uiso 1 1 calc R . . C10 C 0.24771(19) 0.32154(13) 1.01131(10) 0.0114(3) Uani 1 1 d . . . C11 C 0.1531(2) 0.47292(14) 1.12761(11) 0.0179(4) Uani 1 1 d . . . C12 C 0.2562(2) 0.08577(14) 1.01610(11) 0.0178(4) Uani 1 1 d . . . F1 F 0.01634(12) 0.42084(8) 1.12857(7) 0.0248(2) Uani 1 1 d . . . F2 F 0.19987(14) 0.52406(9) 1.20220(7) 0.0309(3) Uani 1 1 d . . . F3 F 0.12344(12) 0.54953(8) 1.06626(6) 0.0224(2) Uani 1 1 d . . . F4 F 0.32850(13) 0.07613(9) 1.09726(7) 0.0291(3) Uani 1 1 d . . . F5 F 0.16909(13) -0.00390(8) 0.99335(7) 0.0294(3) Uani 1 1 d . . . F6 F 0.36832(12) 0.09025(8) 0.96928(7) 0.0277(3) Uani 1 1 d . . . N1 N 0.40443(16) 0.32745(11) 0.89437(8) 0.0107(3) Uani 1 1 d . . . O1 O 0.44132(14) 0.45074(9) 1.10609(7) 0.0168(3) Uani 1 1 d . . . O2 O 0.32037(14) 0.29778(10) 1.17607(7) 0.0173(3) Uani 1 1 d . . . O3 O 0.03053(14) 0.19921(10) 1.06004(8) 0.0182(3) Uani 1 1 d . . . O4 O 0.05599(14) 0.20115(10) 0.90787(7) 0.0201(3) Uani 1 1 d . . . S1 S 0.31004(5) 0.37688(3) 1.10870(2) 0.01163(11) Uani 1 1 d . . . S2 S 0.12669(5) 0.20953(3) 0.99715(3) 0.01262(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 C1 0.0145(8) 0.0093(8) 0.0136(8) 0.0000(6) 0.0034(7) -0.0025(6) C2 0.0173(9) 0.0180(9) 0.0125(8) -0.0016(6) 0.0058(7) 0.0000(7) C3 0.0151(9) 0.0181(9) 0.0188(9) -0.0005(7) 0.0077(7) 0.0018(7) C4 0.0111(8) 0.0160(8) 0.0170(8) 0.0034(7) 0.0023(7) 0.0006(7) C5 0.0143(8) 0.0141(8) 0.0119(8) 0.0017(6) 0.0032(7) -0.0014(7) C6 0.0127(8) 0.0168(9) 0.0120(8) 0.0000(6) 0.0025(6) 0.0010(7) C7 0.0231(9) 0.0183(9) 0.0172(8) 0.0014(7) 0.0000(7) 0.0023(8) C8 0.0174(9) 0.0259(10) 0.0151(8) -0.0041(7) -0.0006(7) 0.0019(7) C9 0.0125(8) 0.0139(8) 0.0115(8) -0.0005(6) 0.0039(6) 0.0023(7) C10 0.0109(8) 0.0124(8) 0.0113(8) -0.0015(6) 0.0029(6) -0.0019(6) C11 0.0210(9) 0.0155(8) 0.0190(8) -0.0033(7) 0.0084(7) -0.0009(7) C12 0.0147(8) 0.0132(8) 0.0258(9) -0.0024(7) 0.0045(7) -0.0023(7) F1 0.0208(6) 0.0207(5) 0.0379(6) -0.0014(5) 0.0176(5) 0.0003(4) F2 0.0408(7) 0.0293(6) 0.0244(6) -0.0148(5) 0.0105(5) 0.0026(5) F3 0.0232(6) 0.0137(5) 0.0309(6) 0.0019(4) 0.0071(4) 0.0023(4) F4 0.0305(6) 0.0214(6) 0.0310(6) 0.0033(4) -0.0036(5) 0.0059(5) F5 0.0226(6) 0.0129(5) 0.0522(7) -0.0073(5) 0.0069(5) -0.0059(4) F6 0.0215(6) 0.0197(5) 0.0467(7) -0.0033(5) 0.0181(5) 0.0024(4) N1 0.0114(7) 0.0108(7) 0.0109(6) 0.0006(5) 0.0042(5) 0.0004(5) O1 0.0164(6) 0.0167(6) 0.0174(6) -0.0028(5) 0.0037(5) -0.0051(5) O2 0.0208(6) 0.0196(6) 0.0119(6) 0.0011(5) 0.0041(5) -0.0012(5) O3 0.0147(6) 0.0182(6) 0.0237(6) -0.0022(5) 0.0086(5) -0.0045(5) O4 0.0169(6) 0.0228(7) 0.0188(6) -0.0056(5) -0.0007(5) -0.0016(5) S1 0.0127(2) 0.0121(2) 0.0106(2) -0.00138(15) 0.00352(15) -0.00132(16) S2 0.0097(2) 0.0127(2) 0.0156(2) -0.00273(15) 0.00301(16) -0.00133(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.365(2) . ? C1 C2 1.392(2) . ? C1 C6 1.516(2) . ? C2 C3 1.385(2) . ? C2 H2 0.9500 . ? C3 C4 1.388(2) . ? C3 H3 0.9500 . ? C4 C5 1.366(2) . ? C4 H4 0.9500 . ? C5 N1 1.353(2) . ? C5 H5 0.9500 . ? C6 C8 1.532(2) . ? C6 C7 1.538(2) . ? C6 H6 1.0000 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C10 1.495(2) . ? C9 N1 1.5156(19) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 S1 1.6799(15) . ? C10 S2 1.6933(16) . ? C11 F2 1.3314(19) . ? C11 F1 1.333(2) . ? C11 F3 1.336(2) . ? C11 S1 1.8484(17) . ? C12 F5 1.325(2) . ? C12 F4 1.325(2) . ? C12 F6 1.335(2) . ? C12 S2 1.8515(18) . ? O1 S1 1.4438(12) . ? O2 S1 1.4313(12) . ? O3 S2 1.4313(12) . ? O4 S2 1.4365(12) . ? 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 C1 C2 117.33(14) . . ? N1 C1 C6 120.26(14) . . ? C2 C1 C6 122.40(14) . . ? C3 C2 C1 121.55(15) . . ? C3 C2 H2 119.2 . . ? C1 C2 H2 119.2 . . ? C2 C3 C4 119.24(15) . . ? C2 C3 H3 120.4 . . ? C4 C3 H3 120.4 . . ? C5 C4 C3 118.29(15) . . ? C5 C4 H4 120.9 . . ? C3 C4 H4 120.9 . . ? N1 C5 C4 122.10(15) . . ? N1 C5 H5 118.9 . . ? C4 C5 H5 118.9 . . ? C1 C6 C8 112.66(14) . . ? C1 C6 C7 110.41(14) . . ? C8 C6 C7 109.70(13) . . ? C1 C6 H6 108.0 . . ? C8 C6 H6 108.0 . . ? C7 C6 H6 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 . . ? C6 C8 H8A 109.5 . . ? C6 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C6 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C10 C9 N1 113.55(13) . . ? C10 C9 H9A 108.9 . . ? N1 C9 H9A 108.9 . . ? C10 C9 H9B 108.9 . . ? N1 C9 H9B 108.9 . . ? H9A C9 H9B 107.7 . . ? C9 C10 S1 120.02(12) . . ? C9 C10 S2 118.46(11) . . ? S1 C10 S2 120.83(9) . . ? F2 C11 F1 108.21(13) . . ? F2 C11 F3 108.25(14) . . ? F1 C11 F3 107.56(14) . . ? F2 C11 S1 110.15(12) . . ? F1 C11 S1 112.01(11) . . ? F3 C11 S1 110.54(11) . . ? F5 C12 F4 108.71(14) . . ? F5 C12 F6 107.95(14) . . ? F4 C12 F6 108.00(14) . . ? F5 C12 S2 109.47(12) . . ? F4 C12 S2 112.06(12) . . ? F6 C12 S2 110.55(12) . . ? C5 N1 C1 121.46(13) . . ? C5 N1 C9 116.15(12) . . ? C1 N1 C9 122.32(13) . . ? O2 S1 O1 120.54(7) . . ? O2 S1 C10 113.03(8) . . ? O1 S1 C10 108.71(7) . . ? O2 S1 C11 103.40(7) . . ? O1 S1 C11 102.25(7) . . ? C10 S1 C11 107.44(8) . . ? O3 S2 O4 120.52(7) . . ? O3 S2 C10 113.62(7) . . ? O4 S2 C10 108.12(8) . . ? O3 S2 C12 103.07(8) . . ? O4 S2 C12 102.81(8) . . ? C10 S2 C12 107.24(8) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.350 _refine_diff_density_min -0.377 _refine_diff_density_rms 0.050 _database_code_depnum_ccdc_archive 'CCDC 948824' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_CBA09-2f #============================================================================== # 2f #============================================================================== _audit_creation_date '5 December 2012' _audit_creation_method SHELXL-97 #============================================================================== # CHEMICAL DATA #============================================================================== _chemical_name_systematic ; 2-(2-Methoxylpyridin-1-ium-1-yl)-1,1-bis((trifluoromethyl)sulfonyl)ethan-1-ide ; _chemical_name_common ? _chemical_melting_point 454 _chemical_formula_moiety 'C10 H9 F6 N O5 S2' _chemical_formula_sum 'C10 H9 F6 N O5 S2' _chemical_formula_weight 401.30 _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_absolute_configuration . 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #============================================================================== # CRYSTAL DATA #============================================================================== _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' 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 9.6307(12) _cell_length_b 10.0920(13) _cell_length_c 14.9590(19) _cell_angle_alpha 90.00 _cell_angle_beta 96.144(2) _cell_angle_gamma 90.00 _cell_volume 1445.6(3) _cell_formula_units_Z 4 _cell_measurement_temperature 90 _cell_measurement_reflns_used 3464 _cell_measurement_theta_min 2.40 _cell_measurement_theta_max 27.47 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.844 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 808 _exptl_absorpt_coefficient_mu 0.464 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.9295 _exptl_absorpt_correction_T_max 0.9683 _exptl_absorpt_process_details ; Crystal Faces plugin in Bruker APEX2 software ; _exptl_special_details ; ? ; #============================================================================== # EXPERIMENTAL DATA #============================================================================== _diffrn_ambient_temperature 90 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker TXS fine-focus rotating anode' _diffrn_radiation_monochromator 'Bruker Helios multilayer confocal mirror' _diffrn_measurement_device_type 'Bruker APEXII CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.333 _diffrn_reflns_number 8230 _diffrn_reflns_av_R_equivalents 0.0229 _diffrn_reflns_av_sigmaI/netI 0.0295 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.40 _diffrn_reflns_theta_max 27.55 _reflns_number_total 3323 _reflns_number_gt 2900 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2006)' _computing_cell_refinement 'APEX2 (Bruker AXS, 2006)' _computing_data_reduction 'SAINT (Bruker AXS, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSHEL (Bruker AXS,2002)' _computing_publication_material 'XCIF (Bruker AXS, 2001)' _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^)+(0.0404P)^2^+0.9149P] 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 3323 _refine_ls_number_parameters 218 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0371 _refine_ls_R_factor_gt 0.0309 _refine_ls_wR_factor_ref 0.0816 _refine_ls_wR_factor_gt 0.0775 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.018 _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 S1 S 0.41566(4) 0.32361(4) 0.15123(3) 0.01213(11) Uani 1 1 d . . . N1 N 0.77335(14) 0.41433(13) 0.08165(9) 0.0101(3) Uani 1 1 d . . . C1 C 0.76013(17) 0.33943(16) 0.00552(11) 0.0116(3) Uani 1 1 d . . . S2 S 0.64967(4) 0.36348(4) 0.28750(3) 0.01089(10) Uani 1 1 d . . . C2 C 0.87860(18) 0.28826(17) -0.02771(11) 0.0146(3) Uani 1 1 d . . . H2 H 0.8706 0.2380 -0.0817 0.018 Uiso 1 1 calc R . . C6 C 0.64777(16) 0.47250(16) 0.11914(11) 0.0102(3) Uani 1 1 d . . . H6A H 0.6769 0.5545 0.1524 0.012 Uiso 1 1 calc R . . H6B H 0.5785 0.4979 0.0683 0.012 Uiso 1 1 calc R . . C7 C 0.57783(17) 0.38283(16) 0.18070(11) 0.0107(3) Uani 1 1 d . . . C3 C 1.00775(18) 0.31155(18) 0.01880(12) 0.0163(4) Uani 1 1 d . . . H3 H 1.0890 0.2748 -0.0022 0.020 Uiso 1 1 calc R . . C5 C 0.90157(17) 0.44072(17) 0.12494(11) 0.0128(3) Uani 1 1 d . . . H5 H 0.9091 0.4968 0.1763 0.015 Uiso 1 1 calc R . . C4 C 1.01975(18) 0.38852(17) 0.09633(12) 0.0152(3) Uani 1 1 d . . . H4 H 1.1085 0.4044 0.1287 0.018 Uiso 1 1 calc R . . C8 C 0.42833(19) 0.14468(18) 0.12448(12) 0.0188(4) Uani 1 1 d . . . O1 O 0.62889(12) 0.32329(12) -0.02943(8) 0.0142(3) Uani 1 1 d . . . O2 O 0.36129(12) 0.37987(12) 0.06606(8) 0.0163(3) Uani 1 1 d . . . O4 O 0.79788(12) 0.38321(13) 0.29258(8) 0.0168(3) Uani 1 1 d . . . O3 O 0.33019(13) 0.32211(13) 0.22402(8) 0.0193(3) Uani 1 1 d . . . O5 O 0.59573(13) 0.25067(12) 0.33073(8) 0.0155(3) Uani 1 1 d . . . C9 C 0.5943(2) 0.50611(18) 0.35280(12) 0.0184(4) Uani 1 1 d . . . C10 C 0.6050(2) 0.2468(2) -0.11147(13) 0.0255(4) Uani 1 1 d . . . H10A H 0.6478 0.2920 -0.1596 0.038 Uiso 1 1 calc R . . H10B H 0.5044 0.2378 -0.1286 0.038 Uiso 1 1 calc R . . H10C H 0.6468 0.1587 -0.1018 0.038 Uiso 1 1 calc R . . F6 F 0.63337(14) 0.61898(11) 0.31667(8) 0.0282(3) Uani 1 1 d . . . F5 F 0.65479(15) 0.49956(12) 0.43664(7) 0.0326(3) Uani 1 1 d . . . F3 F 0.44541(14) 0.07121(11) 0.19788(8) 0.0306(3) Uani 1 1 d . . . F4 F 0.45739(13) 0.51002(12) 0.35517(9) 0.0325(3) Uani 1 1 d . . . F1 F 0.53211(16) 0.11874(12) 0.07691(10) 0.0454(4) Uani 1 1 d . . . F2 F 0.31012(15) 0.10698(12) 0.07833(10) 0.0447(4) 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 0.00834(19) 0.0138(2) 0.0140(2) 0.00355(15) 0.00016(15) -0.00025(14) N1 0.0101(7) 0.0102(7) 0.0104(6) 0.0004(5) 0.0022(5) 0.0000(5) C1 0.0138(8) 0.0092(8) 0.0115(8) 0.0023(6) 0.0007(6) -0.0010(6) S2 0.0122(2) 0.0111(2) 0.00918(19) 0.00092(14) 0.00041(14) 0.00069(14) C2 0.0173(9) 0.0134(8) 0.0136(8) -0.0007(6) 0.0041(6) 0.0014(6) C6 0.0092(7) 0.0102(8) 0.0112(7) 0.0000(6) 0.0022(6) 0.0015(6) C7 0.0094(8) 0.0134(8) 0.0092(7) 0.0011(6) 0.0006(6) 0.0003(6) C3 0.0139(8) 0.0180(9) 0.0180(9) 0.0034(7) 0.0060(7) 0.0033(7) C5 0.0124(8) 0.0141(8) 0.0118(8) 0.0012(6) 0.0003(6) -0.0037(6) C4 0.0102(8) 0.0191(9) 0.0163(8) 0.0028(7) 0.0006(6) -0.0015(6) C8 0.0198(9) 0.0169(9) 0.0183(9) 0.0031(7) -0.0041(7) -0.0048(7) O1 0.0120(6) 0.0153(6) 0.0151(6) -0.0033(5) 0.0000(5) -0.0017(5) O2 0.0120(6) 0.0187(6) 0.0172(6) 0.0058(5) -0.0020(5) -0.0006(5) O4 0.0124(6) 0.0233(7) 0.0141(6) 0.0021(5) -0.0021(5) -0.0010(5) O3 0.0116(6) 0.0271(7) 0.0197(7) 0.0055(5) 0.0044(5) -0.0004(5) O5 0.0196(6) 0.0137(6) 0.0131(6) 0.0030(5) 0.0019(5) -0.0005(5) C9 0.0267(10) 0.0149(9) 0.0138(8) -0.0006(7) 0.0030(7) 0.0016(7) C10 0.0231(10) 0.0285(11) 0.0232(10) -0.0146(8) -0.0055(8) -0.0005(8) F6 0.0495(8) 0.0122(6) 0.0241(6) -0.0016(4) 0.0094(5) -0.0021(5) F5 0.0561(8) 0.0276(7) 0.0125(5) -0.0050(5) -0.0032(5) 0.0075(6) F3 0.0461(8) 0.0167(6) 0.0261(6) 0.0082(5) -0.0099(5) -0.0026(5) F4 0.0281(6) 0.0319(7) 0.0398(7) -0.0124(6) 0.0142(5) 0.0058(5) F1 0.0632(10) 0.0167(6) 0.0631(10) -0.0063(6) 0.0385(8) -0.0024(6) F2 0.0457(8) 0.0238(7) 0.0557(9) 0.0036(6) -0.0352(7) -0.0113(6) _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 O3 1.4336(13) . ? S1 O2 1.4412(12) . ? S1 C7 1.6862(16) . ? S1 C8 1.856(2) . ? N1 C5 1.358(2) . ? N1 C1 1.361(2) . ? N1 C6 1.506(2) . ? C1 O1 1.325(2) . ? C1 C2 1.392(2) . ? S2 O5 1.4339(12) . ? S2 O4 1.4351(13) . ? S2 C7 1.6831(16) . ? S2 C9 1.8497(19) . ? C2 C3 1.379(2) . ? C2 H2 0.9500 . ? C6 C7 1.501(2) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C3 C4 1.390(2) . ? C3 H3 0.9500 . ? C5 C4 1.364(2) . ? C5 H5 0.9500 . ? C4 H4 0.9500 . ? C8 F1 1.314(2) . ? C8 F3 1.320(2) . ? C8 F2 1.323(2) . ? O1 C10 1.447(2) . ? C9 F4 1.323(2) . ? C9 F5 1.327(2) . ? C9 F6 1.332(2) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? 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 O3 S1 O2 119.46(8) . . ? O3 S1 C7 113.35(8) . . ? O2 S1 C7 109.28(8) . . ? O3 S1 C8 102.11(8) . . ? O2 S1 C8 102.63(8) . . ? C7 S1 C8 108.70(8) . . ? C5 N1 C1 120.44(14) . . ? C5 N1 C6 118.14(13) . . ? C1 N1 C6 121.41(13) . . ? O1 C1 N1 113.47(14) . . ? O1 C1 C2 126.67(15) . . ? N1 C1 C2 119.87(15) . . ? O5 S2 O4 119.50(7) . . ? O5 S2 C7 112.85(8) . . ? O4 S2 C7 109.85(8) . . ? O5 S2 C9 103.94(8) . . ? O4 S2 C9 101.85(8) . . ? C7 S2 C9 107.37(8) . . ? C3 C2 C1 119.09(16) . . ? C3 C2 H2 120.5 . . ? C1 C2 H2 120.5 . . ? C7 C6 N1 115.12(13) . . ? C7 C6 H6A 108.5 . . ? N1 C6 H6A 108.5 . . ? C7 C6 H6B 108.5 . . ? N1 C6 H6B 108.5 . . ? H6A C6 H6B 107.5 . . ? C6 C7 S2 119.10(12) . . ? C6 C7 S1 121.14(12) . . ? S2 C7 S1 118.83(10) . . ? C2 C3 C4 120.41(16) . . ? C2 C3 H3 119.8 . . ? C4 C3 H3 119.8 . . ? N1 C5 C4 121.43(16) . . ? N1 C5 H5 119.3 . . ? C4 C5 H5 119.3 . . ? C5 C4 C3 118.68(16) . . ? C5 C4 H4 120.7 . . ? C3 C4 H4 120.7 . . ? F1 C8 F3 107.71(16) . . ? F1 C8 F2 108.79(17) . . ? F3 C8 F2 107.23(15) . . ? F1 C8 S1 112.45(12) . . ? F3 C8 S1 111.85(13) . . ? F2 C8 S1 108.64(13) . . ? C1 O1 C10 117.27(14) . . ? F4 C9 F5 108.30(15) . . ? F4 C9 F6 108.11(15) . . ? F5 C9 F6 108.15(15) . . ? F4 C9 S2 112.44(13) . . ? F5 C9 S2 109.77(12) . . ? F6 C9 S2 109.96(12) . . ? O1 C10 H10A 109.5 . . ? O1 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? O1 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.55 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.521 _refine_diff_density_min -0.392 _refine_diff_density_rms 0.062 _database_code_depnum_ccdc_archive 'CCDC 948825' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_CBA09-2g #============================================================================== # 2g #============================================================================== _audit_creation_date '22 January 2013' _audit_creation_method SHELXL-97 #============================================================================== # CHEMICAL DATA #============================================================================== _chemical_name_systematic ; 2-(2-Fluoropyridin-1-ium-1-yl)-1,1-bis((trifluoromethyl)sulfonyl)ethan-1-ide ; _chemical_name_common ? _chemical_melting_point 425 _chemical_formula_moiety 'C9 H6 F7 N O4 S2' _chemical_formula_sum 'C9 H6 F7 N O4 S2' _chemical_formula_weight 389.27 _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_absolute_configuration . 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #============================================================================== # CRYSTAL DATA #============================================================================== _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' 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 9.6880(10) _cell_length_b 21.565(2) _cell_length_c 13.5597(13) _cell_angle_alpha 90.00 _cell_angle_beta 101.4530(10) _cell_angle_gamma 90.00 _cell_volume 2776.5(5) _cell_formula_units_Z 8 _cell_measurement_temperature 90 _cell_measurement_reflns_used 5288 _cell_measurement_theta_min 2.38 _cell_measurement_theta_max 27.56 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.862 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1552 _exptl_absorpt_coefficient_mu 0.484 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.9030 _exptl_absorpt_correction_T_max 0.9697 _exptl_absorpt_process_details ; Crystal Faces plugin in Bruker APEX2 software ; _exptl_special_details ; ? ; #============================================================================== # EXPERIMENTAL DATA #============================================================================== _diffrn_ambient_temperature 90 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker TXS fine-focus rotating anode' _diffrn_radiation_monochromator 'Bruker Helios multilayer confocal mirror' _diffrn_measurement_device_type 'Bruker APEXII CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.333 _diffrn_reflns_number 13387 _diffrn_reflns_av_R_equivalents 0.0244 _diffrn_reflns_av_sigmaI/netI 0.0277 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.34 _diffrn_reflns_theta_max 25.02 _reflns_number_total 4901 _reflns_number_gt 4075 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2006)' _computing_cell_refinement 'APEX2 (Bruker AXS, 2006)' _computing_data_reduction 'SAINT (Bruker AXS, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSHEL (Bruker AXS,2002)' _computing_publication_material 'XCIF (Bruker AXS, 2001)' _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^)+(0.0585P)^2^+2.0617P] 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 4901 _refine_ls_number_parameters 415 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0456 _refine_ls_R_factor_gt 0.0375 _refine_ls_wR_factor_ref 0.1067 _refine_ls_wR_factor_gt 0.1003 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 1.2760(2) 0.23165(10) 0.36380(17) 0.0140(5) Uani 1 1 d . . . H1 H 1.1766 0.2356 0.3541 0.017 Uiso 1 1 calc R . . C2 C 1.3600(2) 0.28261(11) 0.39172(17) 0.0154(5) Uani 1 1 d . . . H2 H 1.3189 0.3215 0.4017 0.018 Uiso 1 1 calc R . . C3 C 1.5054(2) 0.27677(11) 0.40531(17) 0.0160(5) Uani 1 1 d . . . H3 H 1.5641 0.3117 0.4250 0.019 Uiso 1 1 calc R . . C4 C 1.5646(2) 0.21998(11) 0.39006(17) 0.0158(5) Uani 1 1 d . . . H4 H 1.6635 0.2150 0.3973 0.019 Uiso 1 1 calc R . . C5 C 1.4737(2) 0.17133(11) 0.36405(17) 0.0143(5) Uani 1 1 d . . . C6 C 1.2433(2) 0.11753(10) 0.32624(17) 0.0134(5) Uani 1 1 d . . . H6A H 1.2814 0.0923 0.2767 0.016 Uiso 1 1 calc R . . H6B H 1.2512 0.0926 0.3884 0.016 Uiso 1 1 calc R . . C7 C 1.0915(2) 0.13053(10) 0.28524(17) 0.0126(5) Uani 1 1 d . . . C8 C 1.0313(3) 0.06787(11) 0.09711(18) 0.0208(5) Uani 1 1 d . . . C9 C 0.8934(3) 0.05757(12) 0.3664(2) 0.0262(6) Uani 1 1 d . . . C1B C 0.1863(2) 0.23322(10) 0.65870(16) 0.0137(5) Uani 1 1 d . . . H1B H 0.2856 0.2379 0.6686 0.016 Uiso 1 1 calc R . . C2B C 0.1009(2) 0.28357(11) 0.63123(17) 0.0165(5) Uani 1 1 d . . . H2B H 0.1407 0.3228 0.6216 0.020 Uiso 1 1 calc R . . C3B C -0.0445(2) 0.27672(11) 0.61754(17) 0.0166(5) Uani 1 1 d . . . H3B H -0.1045 0.3113 0.5983 0.020 Uiso 1 1 calc R . . C4B C -0.1013(2) 0.21936(11) 0.63207(17) 0.0154(5) Uani 1 1 d . . . H4B H -0.2001 0.2137 0.6245 0.018 Uiso 1 1 calc R . . C5B C -0.0093(2) 0.17121(11) 0.65776(17) 0.0137(5) Uani 1 1 d . . . C6B C 0.2232(2) 0.11928(10) 0.69552(18) 0.0138(5) Uani 1 1 d . . . H6B1 H 0.1851 0.0932 0.7440 0.017 Uiso 1 1 calc R . . H6B2 H 0.2176 0.0949 0.6330 0.017 Uiso 1 1 calc R . . C7B C 0.3736(2) 0.13325(10) 0.73808(17) 0.0117(5) Uani 1 1 d . . . C8B C 0.4459(3) 0.07378(11) 0.92829(18) 0.0217(6) Uani 1 1 d . . . C9B C 0.5552(3) 0.05556(14) 0.6497(2) 0.0342(7) Uani 1 1 d . . . F1 F 1.52134(14) 0.11488(6) 0.35017(11) 0.0231(3) Uani 1 1 d . . . F2 F 1.15204(18) 0.03675(7) 0.12184(12) 0.0371(4) Uani 1 1 d . . . F3 F 1.00405(17) 0.07593(7) -0.00185(11) 0.0307(4) Uani 1 1 d . . . F4 F 0.93021(19) 0.03360(8) 0.12147(13) 0.0418(5) Uani 1 1 d . . . F5 F 0.9888(2) 0.01291(7) 0.37803(15) 0.0461(5) Uani 1 1 d . . . F6 F 0.80046(19) 0.04720(9) 0.28107(12) 0.0443(5) Uani 1 1 d . . . F7 F 0.82541(18) 0.05549(8) 0.44205(12) 0.0372(4) Uani 1 1 d . . . F1B F -0.05490(14) 0.11434(6) 0.67104(11) 0.0224(3) Uani 1 1 d . . . F2B F 0.3391(2) 0.03577(8) 0.89760(13) 0.0482(5) Uani 1 1 d . . . F3B F 0.45950(18) 0.08276(7) 1.02657(10) 0.0297(4) Uani 1 1 d . . . F4B F 0.5625(2) 0.04654(8) 0.91333(14) 0.0474(5) Uani 1 1 d . . . F5B F 0.4476(3) 0.01673(8) 0.6266(2) 0.0724(8) Uani 1 1 d . . . F6B F 0.6374(3) 0.03769(11) 0.73397(15) 0.0829(9) Uani 1 1 d . . . F7B F 0.6299(2) 0.05294(9) 0.57835(13) 0.0441(5) Uani 1 1 d . . . N1 N 1.33337(19) 0.17602(8) 0.35007(14) 0.0117(4) Uani 1 1 d . . . N1B N 0.13098(19) 0.17699(8) 0.67190(13) 0.0112(4) Uani 1 1 d . . . O1 O 1.16191(17) 0.17136(8) 0.12661(12) 0.0183(4) Uani 1 1 d . . . O2 O 0.90606(17) 0.16916(8) 0.13005(12) 0.0190(4) Uani 1 1 d . . . O3 O 1.05968(19) 0.13875(8) 0.46463(13) 0.0228(4) Uani 1 1 d . . . O4 O 0.86063(18) 0.17435(8) 0.33145(13) 0.0243(4) Uani 1 1 d . . . O1B O 0.29426(17) 0.17130(8) 0.89357(12) 0.0200(4) Uani 1 1 d . . . O2B O 0.55019(17) 0.17901(8) 0.89249(12) 0.0185(4) Uani 1 1 d . . . O3B O 0.41145(19) 0.14532(9) 0.55965(13) 0.0264(4) Uani 1 1 d . . . O4B O 0.6136(2) 0.16953(9) 0.69753(14) 0.0320(5) Uani 1 1 d . . . S1 S 1.04473(6) 0.14411(2) 0.16032(4) 0.01179(15) Uani 1 1 d . . . S2 S 0.97760(6) 0.13391(3) 0.36408(4) 0.01317(15) Uani 1 1 d . . . S3 S 0.41778(6) 0.14846(2) 0.86207(4) 0.01083(15) Uani 1 1 d . . . S4 S 0.48936(6) 0.13494(3) 0.65974(4) 0.01381(15) 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 C1 0.0132(11) 0.0166(12) 0.0120(11) -0.0013(9) 0.0024(9) 0.0024(9) C2 0.0149(12) 0.0155(12) 0.0163(12) -0.0031(9) 0.0044(10) 0.0005(9) C3 0.0168(12) 0.0201(12) 0.0117(11) -0.0022(10) 0.0044(10) -0.0054(10) C4 0.0114(12) 0.0234(13) 0.0127(11) 0.0007(10) 0.0023(9) 0.0004(9) C5 0.0134(12) 0.0178(12) 0.0120(11) 0.0009(9) 0.0035(9) 0.0048(9) C6 0.0137(12) 0.0109(11) 0.0148(12) -0.0019(9) 0.0008(9) 0.0005(9) C7 0.0111(11) 0.0113(11) 0.0144(12) -0.0024(9) 0.0000(9) -0.0009(9) C8 0.0261(14) 0.0190(13) 0.0174(13) -0.0063(10) 0.0048(11) -0.0011(11) C9 0.0307(15) 0.0241(14) 0.0267(14) -0.0042(11) 0.0128(12) -0.0092(12) C1B 0.0133(11) 0.0154(12) 0.0125(11) 0.0017(9) 0.0028(9) -0.0026(9) C2B 0.0174(12) 0.0168(12) 0.0151(12) 0.0042(9) 0.0025(10) -0.0004(9) C3B 0.0156(12) 0.0222(13) 0.0124(11) 0.0029(10) 0.0033(10) 0.0042(10) C4B 0.0096(11) 0.0239(13) 0.0125(11) -0.0005(10) 0.0021(9) 0.0007(9) C5B 0.0141(12) 0.0159(12) 0.0116(11) -0.0018(9) 0.0037(9) -0.0044(9) C6B 0.0137(12) 0.0108(11) 0.0169(12) 0.0012(9) 0.0029(9) 0.0009(9) C7B 0.0105(11) 0.0129(11) 0.0125(11) 0.0020(9) 0.0045(9) -0.0010(8) C8B 0.0340(15) 0.0139(12) 0.0168(13) 0.0030(10) 0.0041(11) 0.0002(11) C9B 0.0414(18) 0.0342(17) 0.0339(17) 0.0031(13) 0.0244(14) 0.0145(14) F1 0.0140(7) 0.0171(8) 0.0381(9) -0.0040(6) 0.0049(6) 0.0047(5) F2 0.0432(10) 0.0265(9) 0.0370(9) -0.0139(7) -0.0033(8) 0.0163(7) F3 0.0446(10) 0.0308(9) 0.0155(8) -0.0101(6) 0.0029(7) 0.0014(7) F4 0.0568(12) 0.0299(9) 0.0453(10) -0.0209(8) 0.0263(9) -0.0265(8) F5 0.0635(13) 0.0183(9) 0.0647(13) 0.0081(8) 0.0326(10) 0.0015(8) F6 0.0453(11) 0.0578(12) 0.0315(10) -0.0170(8) 0.0119(8) -0.0359(9) F7 0.0416(10) 0.0445(10) 0.0317(9) 0.0007(8) 0.0225(8) -0.0174(8) F1B 0.0154(7) 0.0164(7) 0.0357(9) 0.0015(6) 0.0056(6) -0.0052(6) F2B 0.0748(14) 0.0253(9) 0.0343(10) 0.0121(7) -0.0140(9) -0.0291(9) F3B 0.0502(10) 0.0227(8) 0.0144(7) 0.0064(6) 0.0022(7) -0.0012(7) F4B 0.0690(13) 0.0351(10) 0.0427(11) 0.0188(8) 0.0219(10) 0.0354(9) F5B 0.0950(18) 0.0214(10) 0.123(2) -0.0230(11) 0.0753(16) -0.0132(10) F6B 0.114(2) 0.0973(18) 0.0439(12) 0.0304(12) 0.0313(13) 0.0903(16) F7B 0.0490(11) 0.0498(11) 0.0420(10) -0.0052(8) 0.0296(9) 0.0167(9) N1 0.0106(10) 0.0137(10) 0.0106(9) -0.0002(7) 0.0014(8) 0.0002(7) N1B 0.0104(10) 0.0139(10) 0.0092(9) 0.0000(7) 0.0015(8) 0.0001(7) O1 0.0178(9) 0.0239(9) 0.0137(8) 0.0006(7) 0.0043(7) -0.0018(7) O2 0.0153(9) 0.0240(9) 0.0162(9) -0.0027(7) -0.0008(7) 0.0052(7) O3 0.0210(10) 0.0327(10) 0.0147(9) -0.0049(7) 0.0036(7) -0.0027(8) O4 0.0203(10) 0.0304(10) 0.0246(10) 0.0035(8) 0.0105(8) 0.0099(8) O1B 0.0165(9) 0.0272(10) 0.0171(9) 0.0000(7) 0.0052(7) 0.0065(7) O2B 0.0161(9) 0.0225(9) 0.0161(9) 0.0010(7) 0.0011(7) -0.0072(7) O3B 0.0241(10) 0.0411(11) 0.0146(9) 0.0062(8) 0.0052(8) 0.0058(8) O4B 0.0231(10) 0.0479(13) 0.0288(11) -0.0134(9) 0.0142(9) -0.0188(9) S1 0.0117(3) 0.0121(3) 0.0112(3) -0.0024(2) 0.0014(2) -0.0003(2) S2 0.0126(3) 0.0149(3) 0.0123(3) -0.0020(2) 0.0032(2) -0.0005(2) S3 0.0119(3) 0.0093(3) 0.0111(3) 0.0017(2) 0.0018(2) -0.0004(2) S4 0.0133(3) 0.0158(3) 0.0130(3) 0.0008(2) 0.0042(2) -0.0008(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 C1 N1 1.351(3) . ? C1 C2 1.375(3) . ? C1 H1 0.9500 . ? C2 C3 1.390(3) . ? C2 H2 0.9500 . ? C3 C4 1.385(3) . ? C3 H3 0.9500 . ? C4 C5 1.370(3) . ? C4 H4 0.9500 . ? C5 F1 1.328(3) . ? C5 N1 1.339(3) . ? C6 C7 1.493(3) . ? C6 N1 1.531(3) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 S2 1.683(2) . ? C7 S1 1.690(2) . ? C8 F4 1.320(3) . ? C8 F3 1.327(3) . ? C8 F2 1.332(3) . ? C8 S1 1.847(2) . ? C9 F5 1.322(3) . ? C9 F7 1.326(3) . ? C9 F6 1.336(3) . ? C9 S2 1.840(3) . ? C1B N1B 1.352(3) . ? C1B C2B 1.371(3) . ? C1B H1B 0.9500 . ? C2B C3B 1.392(3) . ? C2B H2B 0.9500 . ? C3B C4B 1.384(3) . ? C3B H3B 0.9500 . ? C4B C5B 1.368(3) . ? C4B H4B 0.9500 . ? C5B F1B 1.328(3) . ? C5B N1B 1.340(3) . ? C6B C7B 1.488(3) . ? C6B N1B 1.528(3) . ? C6B H6B1 0.9900 . ? C6B H6B2 0.9900 . ? C7B S3 1.683(2) . ? C7B S4 1.691(2) . ? C8B F2B 1.321(3) . ? C8B F4B 1.324(3) . ? C8B F3B 1.327(3) . ? C8B S3 1.838(2) . ? C9B F6B 1.314(4) . ? C9B F7B 1.319(3) . ? C9B F5B 1.325(4) . ? C9B S4 1.841(3) . ? O1 S1 1.4315(17) . ? O2 S1 1.4303(17) . ? O3 S2 1.4393(18) . ? O4 S2 1.4287(18) . ? O1B S3 1.4353(17) . ? O2B S3 1.4281(17) . ? O3B S4 1.4334(18) . ? O4B S4 1.4220(18) . ? 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 C1 C2 120.7(2) . . ? N1 C1 H1 119.6 . . ? C2 C1 H1 119.6 . . ? C1 C2 C3 119.5(2) . . ? C1 C2 H2 120.2 . . ? C3 C2 H2 120.2 . . ? C4 C3 C2 119.9(2) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C5 C4 C3 116.9(2) . . ? C5 C4 H4 121.6 . . ? C3 C4 H4 121.6 . . ? F1 C5 N1 114.87(19) . . ? F1 C5 C4 121.0(2) . . ? N1 C5 C4 124.1(2) . . ? C7 C6 N1 113.71(18) . . ? C7 C6 H6A 108.8 . . ? N1 C6 H6A 108.8 . . ? C7 C6 H6B 108.8 . . ? N1 C6 H6B 108.8 . . ? H6A C6 H6B 107.7 . . ? C6 C7 S2 119.57(17) . . ? C6 C7 S1 116.99(17) . . ? S2 C7 S1 123.38(13) . . ? F4 C8 F3 108.5(2) . . ? F4 C8 F2 108.2(2) . . ? F3 C8 F2 108.0(2) . . ? F4 C8 S1 111.70(17) . . ? F3 C8 S1 109.54(17) . . ? F2 C8 S1 110.75(17) . . ? F5 C9 F7 109.0(2) . . ? F5 C9 F6 108.4(2) . . ? F7 C9 F6 108.2(2) . . ? F5 C9 S2 110.61(19) . . ? F7 C9 S2 109.48(18) . . ? F6 C9 S2 111.09(19) . . ? N1B C1B C2B 120.8(2) . . ? N1B C1B H1B 119.6 . . ? C2B C1B H1B 119.6 . . ? C1B C2B C3B 119.5(2) . . ? C1B C2B H2B 120.2 . . ? C3B C2B H2B 120.2 . . ? C4B C3B C2B 119.8(2) . . ? C4B C3B H3B 120.1 . . ? C2B C3B H3B 120.1 . . ? C5B C4B C3B 117.2(2) . . ? C5B C4B H4B 121.4 . . ? C3B C4B H4B 121.4 . . ? F1B C5B N1B 114.9(2) . . ? F1B C5B C4B 121.2(2) . . ? N1B C5B C4B 123.8(2) . . ? C7B C6B N1B 113.78(18) . . ? C7B C6B H6B1 108.8 . . ? N1B C6B H6B1 108.8 . . ? C7B C6B H6B2 108.8 . . ? N1B C6B H6B2 108.8 . . ? H6B1 C6B H6B2 107.7 . . ? C6B C7B S3 117.53(17) . . ? C6B C7B S4 118.77(17) . . ? S3 C7B S4 123.68(13) . . ? F2B C8B F4B 108.4(2) . . ? F2B C8B F3B 108.8(2) . . ? F4B C8B F3B 107.5(2) . . ? F2B C8B S3 111.05(18) . . ? F4B C8B S3 111.23(18) . . ? F3B C8B S3 109.77(16) . . ? F6B C9B F7B 107.4(2) . . ? F6B C9B F5B 109.4(3) . . ? F7B C9B F5B 108.7(3) . . ? F6B C9B S4 111.6(2) . . ? F7B C9B S4 110.0(2) . . ? F5B C9B S4 109.7(2) . . ? C5 N1 C1 118.79(19) . . ? C5 N1 C6 119.19(18) . . ? C1 N1 C6 121.88(18) . . ? C5B N1B C1B 118.81(19) . . ? C5B N1B C6B 119.22(18) . . ? C1B N1B C6B 121.84(19) . . ? O2 S1 O1 120.84(10) . . ? O2 S1 C7 113.73(11) . . ? O1 S1 C7 108.65(10) . . ? O2 S1 C8 103.14(11) . . ? O1 S1 C8 101.80(11) . . ? C7 S1 C8 106.92(11) . . ? O4 S2 O3 120.28(11) . . ? O4 S2 C7 114.16(11) . . ? O3 S2 C7 107.24(11) . . ? O4 S2 C9 102.96(12) . . ? O3 S2 C9 102.25(12) . . ? C7 S2 C9 108.70(12) . . ? O2B S3 O1B 120.66(10) . . ? O2B S3 C7B 114.46(11) . . ? O1B S3 C7B 107.61(10) . . ? O2B S3 C8B 103.05(11) . . ? O1B S3 C8B 101.93(11) . . ? C7B S3 C8B 107.52(11) . . ? O4B S4 O3B 120.54(12) . . ? O4B S4 C7B 113.84(11) . . ? O3B S4 C7B 107.93(11) . . ? O4B S4 C9B 103.50(14) . . ? O3B S4 C9B 101.56(13) . . ? C7B S4 C9B 108.00(12) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.939 _refine_diff_density_min -0.383 _refine_diff_density_rms 0.072 _database_code_depnum_ccdc_archive 'CCDC 948826' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_CBA09-2h #============================================================================== # 2h #============================================================================== _audit_creation_date '31 August 2012' _audit_creation_method SHELXL-97 #============================================================================== # CHEMICAL DATA #============================================================================== _chemical_name_systematic ; 2-(2-Chloropyridin-1-ium-1-yl)-1,1-bis((trifluoromethyl)sulfonyl)ethan-1-ide ; _chemical_name_common ? _chemical_melting_point 438 _chemical_formula_moiety 'C9 H6 Cl F6 N O4 S2' _chemical_formula_sum 'C9 H6 Cl F6 N O4 S2' _chemical_formula_weight 405.72 _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_absolute_configuration . 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #============================================================================== # CRYSTAL DATA #============================================================================== _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c ' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 9.8403(17) _cell_length_b 21.718(4) _cell_length_c 13.666(2) _cell_angle_alpha 90.00 _cell_angle_beta 103.359(2) _cell_angle_gamma 90.00 _cell_volume 2841.4(9) _cell_formula_units_Z 8 _cell_measurement_temperature 90 _cell_measurement_reflns_used 1197 _cell_measurement_theta_min 2.42 _cell_measurement_theta_max 26.37 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.897 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1616 _exptl_absorpt_coefficient_mu 0.650 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7371 _exptl_absorpt_correction_T_max 0.8544 _exptl_absorpt_process_details ; SADABS Sheldrick 1996 ; _exptl_special_details ; ? ; #============================================================================== # EXPERIMENTAL DATA #============================================================================== _diffrn_ambient_temperature 90 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker TXS fine-focus rotating anode' _diffrn_radiation_monochromator 'Bruker Helios multilayer confocal mirror' _diffrn_measurement_device_type 'Bruker APEXII CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.333 _diffrn_reflns_number 6772 _diffrn_reflns_av_R_equivalents 0.0467 _diffrn_reflns_av_sigmaI/netI 0.0572 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.32 _diffrn_reflns_theta_max 25.03 _reflns_number_total 2510 _reflns_number_gt 1873 _reflns_threshold_expression >2sigma _computing_data_collection 'APEX2 ' _computing_cell_refinement 'APEX2 (Bruker AXS, 2006)' _computing_data_reduction 'SAINT (Bruker AXS, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSHEL (Bruker AXS,2002)' _computing_publication_material 'XCIF (Bruker AXS, 2001)' _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^)+(0.0344P)^2^+0.6434P] 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 2510 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0617 _refine_ls_R_factor_gt 0.0374 _refine_ls_wR_factor_ref 0.0807 _refine_ls_wR_factor_gt 0.0733 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_restrained_S_all 1.009 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.7458(3) 0.16927(13) 0.0970(2) 0.0150(7) Uani 1 1 d . . . C2 C 0.8359(3) 0.21794(14) 0.1251(2) 0.0162(7) Uani 1 1 d . . . H2 H 0.9336 0.2128 0.1324 0.019 Uiso 1 1 calc R . . C3 C 0.7819(3) 0.27424(14) 0.1424(2) 0.0168(7) Uani 1 1 d . . . H3 H 0.8423 0.3083 0.1632 0.020 Uiso 1 1 calc R . . C4 C 0.6388(3) 0.28101(14) 0.1292(2) 0.0165(7) Uani 1 1 d . . . H4 H 0.6001 0.3198 0.1399 0.020 Uiso 1 1 calc R . . C5 C 0.5536(3) 0.23115(13) 0.1007(2) 0.0153(7) Uani 1 1 d . . . H5 H 0.4555 0.2357 0.0920 0.018 Uiso 1 1 calc R . . C6 C 0.5096(3) 0.12004(13) 0.0605(2) 0.0147(7) Uani 1 1 d . . . H6A H 0.5405 0.0944 0.0098 0.018 Uiso 1 1 calc R . . H6B H 0.5189 0.0949 0.1221 0.018 Uiso 1 1 calc R . . C7 C 0.3592(3) 0.13587(13) 0.0215(2) 0.0120(6) Uani 1 1 d . . . C8 C 0.2074(3) 0.05398(15) 0.1164(2) 0.0229(8) Uani 1 1 d . . . C9 C 0.2624(4) 0.07844(14) -0.1693(2) 0.0230(8) Uani 1 1 d . . . Cl1 Cl 0.80925(8) 0.09808(3) 0.07563(6) 0.0244(2) Uani 1 1 d . . . F1 F 0.3231(2) 0.02001(9) 0.13823(17) 0.0450(6) Uani 1 1 d . . . F2 F 0.14177(19) 0.04787(9) 0.18984(14) 0.0329(5) Uani 1 1 d . . . F3 F 0.1260(2) 0.03191(9) 0.03348(15) 0.0435(6) Uani 1 1 d . . . F4 F 0.3628(2) 0.03672(8) -0.13941(14) 0.0404(6) Uani 1 1 d . . . F5 F 0.1439(2) 0.05469(9) -0.15502(14) 0.0414(6) Uani 1 1 d . . . F6 F 0.2467(2) 0.08720(8) -0.26759(13) 0.0303(5) Uani 1 1 d . . . N1 N 0.6067(2) 0.17573(10) 0.08482(17) 0.0112(5) Uani 1 1 d . . . O1 O 0.3329(2) 0.14943(10) 0.20084(15) 0.0230(5) Uani 1 1 d . . . O2 O 0.1212(2) 0.16428(9) 0.06266(15) 0.0207(5) Uani 1 1 d . . . O3 O 0.4274(2) 0.17080(10) -0.13623(15) 0.0220(5) Uani 1 1 d . . . O4 O 0.1790(2) 0.18501(9) -0.12884(15) 0.0198(5) Uani 1 1 d . . . S1 S 0.25258(8) 0.13519(3) 0.10192(6) 0.01522(19) Uani 1 1 d . . . S2 S 0.30651(8) 0.15146(3) -0.10192(6) 0.01367(19) 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 C1 0.0172(17) 0.0137(16) 0.0144(16) -0.0001(13) 0.0044(13) 0.0037(13) C2 0.0101(15) 0.0254(17) 0.0138(16) -0.0020(14) 0.0044(13) -0.0010(13) C3 0.0192(18) 0.0204(17) 0.0100(16) -0.0021(14) 0.0016(13) -0.0058(14) C4 0.0207(18) 0.0172(16) 0.0113(16) -0.0007(13) 0.0030(14) 0.0005(14) C5 0.0137(17) 0.0161(16) 0.0156(17) 0.0007(13) 0.0022(13) 0.0015(13) C6 0.0126(16) 0.0113(15) 0.0192(17) -0.0001(13) 0.0020(13) -0.0048(13) C7 0.0108(16) 0.0128(15) 0.0115(15) 0.0018(13) 0.0008(12) 0.0012(12) C8 0.0223(19) 0.0251(19) 0.023(2) 0.0032(15) 0.0096(16) -0.0015(15) C9 0.032(2) 0.0167(17) 0.0173(19) -0.0008(14) -0.0015(15) 0.0008(15) Cl1 0.0159(4) 0.0171(4) 0.0408(5) -0.0009(4) 0.0078(4) 0.0038(3) F1 0.0408(13) 0.0247(11) 0.0771(16) 0.0213(11) 0.0296(12) 0.0096(10) F2 0.0357(12) 0.0347(12) 0.0343(12) 0.0112(9) 0.0200(10) -0.0049(9) F3 0.0588(15) 0.0354(13) 0.0369(13) -0.0084(10) 0.0123(11) -0.0299(11) F4 0.0640(15) 0.0192(11) 0.0304(12) -0.0053(9) -0.0047(11) 0.0155(10) F5 0.0538(14) 0.0361(13) 0.0332(12) -0.0094(10) 0.0081(11) -0.0293(11) F6 0.0540(13) 0.0211(11) 0.0138(10) -0.0026(8) 0.0038(9) 0.0031(9) N1 0.0110(13) 0.0111(13) 0.0115(13) 0.0015(10) 0.0025(11) 0.0006(10) O1 0.0228(13) 0.0341(14) 0.0109(11) -0.0035(10) 0.0018(10) -0.0068(10) O2 0.0138(11) 0.0260(13) 0.0242(12) 0.0044(10) 0.0086(10) 0.0049(10) O3 0.0203(12) 0.0291(13) 0.0185(12) 0.0026(10) 0.0082(10) -0.0042(10) O4 0.0185(12) 0.0224(12) 0.0174(12) 0.0005(10) 0.0019(9) 0.0081(9) S1 0.0136(4) 0.0162(4) 0.0163(4) -0.0002(3) 0.0045(3) -0.0009(3) S2 0.0155(4) 0.0115(4) 0.0138(4) -0.0002(3) 0.0030(3) 0.0003(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.348(4) . ? C1 C2 1.376(4) . ? C1 Cl1 1.717(3) . ? C2 C3 1.375(4) . ? C2 H2 0.9500 . ? C3 C4 1.385(4) . ? C3 H3 0.9500 . ? C4 C5 1.369(4) . ? C4 H4 0.9500 . ? C5 N1 1.349(4) . ? C5 H5 0.9500 . ? C6 C7 1.492(4) . ? C6 N1 1.530(3) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 S2 1.681(3) . ? C7 S1 1.686(3) . ? C8 F3 1.317(4) . ? C8 F2 1.320(4) . ? C8 F1 1.331(4) . ? C8 S1 1.841(3) . ? C9 F6 1.329(3) . ? C9 F5 1.330(4) . ? C9 F4 1.333(4) . ? C9 S2 1.835(3) . ? O1 S1 1.433(2) . ? O2 S1 1.427(2) . ? O3 S2 1.438(2) . ? O4 S2 1.424(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 N1 C1 C2 121.7(3) . . ? N1 C1 Cl1 118.1(2) . . ? C2 C1 Cl1 120.2(2) . . ? C3 C2 C1 118.8(3) . . ? C3 C2 H2 120.6 . . ? C1 C2 H2 120.6 . . ? C2 C3 C4 119.6(3) . . ? C2 C3 H3 120.2 . . ? C4 C3 H3 120.2 . . ? C5 C4 C3 119.3(3) . . ? C5 C4 H4 120.3 . . ? C3 C4 H4 120.3 . . ? N1 C5 C4 121.1(3) . . ? N1 C5 H5 119.4 . . ? C4 C5 H5 119.4 . . ? C7 C6 N1 114.4(2) . . ? C7 C6 H6A 108.7 . . ? N1 C6 H6A 108.7 . . ? C7 C6 H6B 108.7 . . ? N1 C6 H6B 108.7 . . ? H6A C6 H6B 107.6 . . ? C6 C7 S2 117.1(2) . . ? C6 C7 S1 118.7(2) . . ? S2 C7 S1 124.18(17) . . ? F3 C8 F2 108.1(3) . . ? F3 C8 F1 108.1(3) . . ? F2 C8 F1 108.5(3) . . ? F3 C8 S1 111.7(2) . . ? F2 C8 S1 110.5(2) . . ? F1 C8 S1 109.9(2) . . ? F6 C9 F5 107.6(3) . . ? F6 C9 F4 108.2(3) . . ? F5 C9 F4 107.7(3) . . ? F6 C9 S2 110.0(2) . . ? F5 C9 S2 112.0(2) . . ? F4 C9 S2 111.1(2) . . ? C5 N1 C1 119.5(2) . . ? C5 N1 C6 119.7(2) . . ? C1 N1 C6 120.7(2) . . ? O2 S1 O1 120.88(13) . . ? O2 S1 C7 113.40(13) . . ? O1 S1 C7 108.80(13) . . ? O2 S1 C8 104.14(14) . . ? O1 S1 C8 101.52(14) . . ? C7 S1 C8 106.30(14) . . ? O4 S2 O3 120.81(13) . . ? O4 S2 C7 114.30(13) . . ? O3 S2 C7 107.42(13) . . ? O4 S2 C9 102.73(14) . . ? O3 S2 C9 101.90(14) . . ? C7 S2 C9 108.19(14) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.367 _refine_diff_density_min -0.346 _refine_diff_density_rms 0.074 _database_code_depnum_ccdc_archive 'CCDC 948827' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_CBA09-2i #============================================================================== # 2i #============================================================================== _audit_creation_date 'January 9 2013' _audit_creation_method SHELXL-97 #============================================================================== # CHEMICAL DATA #============================================================================== _chemical_name_systematic ; 2-(2-Bromopyridin-1-ium-1-yl)-1,1-bis((trifluoromethyl)sulfonyl)ethan-1-ide ; _chemical_name_common ? _chemical_melting_point 438 _chemical_formula_moiety 'C9 H6 Br F6 N O4 S2' _chemical_formula_sum 'C9 H6 Br F6 N O4 S2' _chemical_formula_weight 450.18 _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_absolute_configuration . 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #============================================================================== # CRYSTAL DATA #============================================================================== _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c ' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 9.926(2) _cell_length_b 21.888(5) _cell_length_c 13.659(3) _cell_angle_alpha 90.00 _cell_angle_beta 103.046(3) _cell_angle_gamma 90.00 _cell_volume 2891.1(12) _cell_formula_units_Z 8 _cell_measurement_temperature 90 _cell_measurement_reflns_used 4172 _cell_measurement_theta_min 2.30 _cell_measurement_theta_max 27.62 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.069 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1760 _exptl_absorpt_coefficient_mu 3.218 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.5248 _exptl_absorpt_correction_T_max 0.8304 _exptl_absorpt_process_details ; Crystal Faces plugin in Bruker APEX2 software ; _exptl_special_details ; ? ; #============================================================================== # EXPERIMENTAL DATA #============================================================================== _diffrn_ambient_temperature 90 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker TXS fine-focus rotating anode' _diffrn_radiation_monochromator 'Bruker Helios multilayer confocal mirror' _diffrn_measurement_device_type 'Bruker APEXII CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.333 _diffrn_reflns_number 6803 _diffrn_reflns_av_R_equivalents 0.1148 _diffrn_reflns_av_sigmaI/netI 0.0787 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.30 _diffrn_reflns_theta_max 25.02 _reflns_number_total 2551 _reflns_number_gt 2227 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2006)' _computing_cell_refinement 'APEX2 (Bruker AXS, 2006)' _computing_data_reduction 'SAINT (Bruker AXS, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSHEL (Bruker AXS,2002)' _computing_publication_material 'XCIF (Bruker AXS, 2001)' _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^)+(0.0303P)^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_number_reflns 2551 _refine_ls_number_parameters 208 _refine_ls_number_restraints 120 _refine_ls_R_factor_all 0.0373 _refine_ls_R_factor_gt 0.0331 _refine_ls_wR_factor_ref 0.0702 _refine_ls_wR_factor_gt 0.0687 _refine_ls_goodness_of_fit_ref 0.987 _refine_ls_restrained_S_all 0.963 _refine_ls_shift/su_max 0.002 _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 N1 N 1.10466(19) 0.17678(11) 0.08355(13) 0.0123(5) Uani 1 1 d U . . C1 C 1.2432(2) 0.16987(13) 0.09329(15) 0.0120(6) Uani 1 1 d U . . C2 C 1.3327(2) 0.21771(13) 0.12214(16) 0.0142(6) Uani 1 1 d U . . H2 H 1.4292 0.2124 0.1283 0.017 Uiso 1 1 calc R . . C3 C 1.2806(2) 0.27384(14) 0.14208(15) 0.0158(6) Uani 1 1 d U . . H3 H 1.3410 0.3074 0.1629 0.019 Uiso 1 1 calc R . . C4 C 1.1390(2) 0.28034(14) 0.13125(16) 0.0154(6) Uani 1 1 d U . . H4 H 1.1012 0.3186 0.1438 0.018 Uiso 1 1 calc R . . C5 C 1.0545(2) 0.23138(13) 0.10240(16) 0.0142(6) Uani 1 1 d U . . H5 H 0.9576 0.2360 0.0955 0.017 Uiso 1 1 calc R . . C6 C 1.0079(2) 0.12176(13) 0.05958(16) 0.0141(6) Uani 1 1 d U . . H6A H 1.0380 0.0962 0.0086 0.017 Uiso 1 1 calc R . . H6B H 1.0170 0.0968 0.1212 0.017 Uiso 1 1 calc R . . C7 C 0.8604(2) 0.13765(13) 0.02184(15) 0.0116(5) Uani 1 1 d U . . C8 C 0.7094(3) 0.05653(14) 0.11673(18) 0.0190(6) Uani 1 1 d U . . C9 C 0.7663(3) 0.07989(15) -0.16928(18) 0.0229(7) Uani 1 1 d U . . F1 F 0.82334(16) 0.02187(9) 0.13619(12) 0.0333(4) Uani 1 1 d U . . F2 F 0.64591(16) 0.04983(8) 0.19212(10) 0.0299(4) Uani 1 1 d U . . F3 F 0.62490(16) 0.03461(8) 0.03385(11) 0.0277(4) Uani 1 1 d U . . F4 F 0.64867(18) 0.05618(9) -0.15564(11) 0.0342(5) Uani 1 1 d U . . F5 F 0.86680(18) 0.03928(9) -0.13847(11) 0.0358(5) Uani 1 1 d U . . F6 F 0.75219(18) 0.08864(8) -0.26773(10) 0.0287(4) Uani 1 1 d U . . O1 O 0.83461(17) 0.15063(10) 0.20168(11) 0.0206(5) Uani 1 1 d U . . O2 O 0.62358(16) 0.16623(10) 0.06401(12) 0.0184(4) Uani 1 1 d U . . O3 O 0.92591(16) 0.17297(9) -0.13633(11) 0.0188(4) Uani 1 1 d U . . O4 O 0.67909(16) 0.18542(9) -0.12918(11) 0.0192(4) Uani 1 1 d U . . S1 S 0.75384(6) 0.13686(3) 0.10266(4) 0.01359(16) Uani 1 1 d U . . S2 S 0.80689(6) 0.15304(3) -0.10216(4) 0.01252(16) Uani 1 1 d U . . Br1 Br 1.31189(2) 0.093807(14) 0.064851(18) 0.02054(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 N1 0.0075(9) 0.0213(14) 0.0074(9) -0.0007(8) -0.0001(7) -0.0016(10) C1 0.0109(11) 0.0163(16) 0.0086(11) 0.0019(9) 0.0017(9) 0.0023(12) C2 0.0074(11) 0.0243(18) 0.0108(11) 0.0011(10) 0.0016(9) -0.0019(12) C3 0.0136(12) 0.0256(18) 0.0075(11) -0.0033(10) 0.0009(9) -0.0051(13) C4 0.0133(12) 0.0208(17) 0.0116(12) -0.0021(10) 0.0021(9) 0.0006(12) C5 0.0078(11) 0.0231(17) 0.0117(12) -0.0016(11) 0.0023(9) 0.0017(12) C6 0.0089(11) 0.0198(16) 0.0127(11) -0.0004(10) 0.0009(9) -0.0006(12) C7 0.0061(10) 0.0191(16) 0.0089(11) 0.0001(10) 0.0002(8) -0.0001(12) C8 0.0134(12) 0.0245(18) 0.0198(13) 0.0030(11) 0.0052(10) -0.0011(13) C9 0.0295(15) 0.0254(19) 0.0120(12) -0.0020(11) 0.0007(11) -0.0016(15) F1 0.0214(8) 0.0303(12) 0.0496(10) 0.0151(8) 0.0111(7) 0.0056(9) F2 0.0285(9) 0.0412(13) 0.0236(8) 0.0084(7) 0.0138(6) -0.0050(9) F3 0.0269(8) 0.0290(11) 0.0270(8) -0.0073(7) 0.0054(6) -0.0115(8) F4 0.0388(10) 0.0361(12) 0.0273(9) -0.0088(7) 0.0065(7) -0.0214(9) F5 0.0482(11) 0.0257(12) 0.0273(9) -0.0042(7) -0.0048(7) 0.0153(10) F6 0.0477(11) 0.0280(11) 0.0092(7) -0.0034(6) 0.0043(7) 0.0013(9) O1 0.0153(9) 0.0356(14) 0.0102(9) -0.0037(8) 0.0013(7) -0.0049(9) O2 0.0075(8) 0.0279(13) 0.0209(9) 0.0015(8) 0.0052(7) 0.0028(8) O3 0.0127(8) 0.0299(13) 0.0150(8) 0.0027(8) 0.0055(7) -0.0022(9) O4 0.0131(8) 0.0293(13) 0.0138(8) 0.0007(7) 0.0001(6) 0.0061(9) S1 0.0080(3) 0.0221(4) 0.0107(3) -0.0009(2) 0.0021(2) -0.0007(3) S2 0.0089(3) 0.0186(4) 0.0097(3) -0.0003(2) 0.0013(2) 0.0004(3) Br1 0.00852(14) 0.0218(2) 0.03160(17) -0.00131(11) 0.00523(11) 0.00244(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 N1 C5 1.342(3) . ? N1 C1 1.360(3) . ? N1 C6 1.529(3) . ? C1 C2 1.372(4) . ? C1 Br1 1.873(3) . ? C2 C3 1.383(4) . ? C2 H2 0.9500 . ? C3 C4 1.387(3) . ? C3 H3 0.9500 . ? C4 C5 1.363(4) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C6 C7 1.480(3) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 S1 1.692(2) . ? C7 S2 1.691(2) . ? C8 F2 1.331(3) . ? C8 F3 1.336(3) . ? C8 F1 1.338(3) . ? C8 S1 1.833(3) . ? C9 F4 1.329(3) . ? C9 F5 1.331(3) . ? C9 F6 1.334(3) . ? C9 S2 1.844(3) . ? O1 S1 1.4399(16) . ? O2 S1 1.4337(18) . ? O3 S2 1.4328(17) . ? O4 S2 1.4269(18) . ? 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 C5 N1 C1 119.4(2) . . ? C5 N1 C6 120.00(19) . . ? C1 N1 C6 120.4(2) . . ? N1 C1 C2 121.2(3) . . ? N1 C1 Br1 119.1(2) . . ? C2 C1 Br1 119.73(18) . . ? C1 C2 C3 119.2(2) . . ? C1 C2 H2 120.4 . . ? C3 C2 H2 120.4 . . ? C2 C3 C4 119.0(3) . . ? C2 C3 H3 120.5 . . ? C4 C3 H3 120.5 . . ? C5 C4 C3 119.5(3) . . ? C5 C4 H4 120.2 . . ? C3 C4 H4 120.2 . . ? N1 C5 C4 121.6(2) . . ? N1 C5 H5 119.2 . . ? C4 C5 H5 119.2 . . ? C7 C6 N1 114.5(2) . . ? C7 C6 H6A 108.6 . . ? N1 C6 H6A 108.6 . . ? C7 C6 H6B 108.6 . . ? N1 C6 H6B 108.6 . . ? H6A C6 H6B 107.6 . . ? C6 C7 S1 119.02(16) . . ? C6 C7 S2 117.27(16) . . ? S1 C7 S2 123.67(13) . . ? F2 C8 F3 107.4(2) . . ? F2 C8 F1 108.1(2) . . ? F3 C8 F1 107.8(2) . . ? F2 C8 S1 110.72(19) . . ? F3 C8 S1 112.04(18) . . ? F1 C8 S1 110.60(18) . . ? F4 C9 F5 108.3(3) . . ? F4 C9 F6 107.6(2) . . ? F5 C9 F6 108.4(2) . . ? F4 C9 S2 111.70(19) . . ? F5 C9 S2 111.01(18) . . ? F6 C9 S2 109.8(2) . . ? O2 S1 O1 121.11(11) . . ? O2 S1 C7 113.55(11) . . ? O1 S1 C7 108.25(11) . . ? O2 S1 C8 104.49(12) . . ? O1 S1 C8 101.45(12) . . ? C7 S1 C8 106.19(12) . . ? O4 S2 O3 120.98(11) . . ? O4 S2 C7 114.71(10) . . ? O3 S2 C7 106.95(10) . . ? O4 S2 C9 102.76(12) . . ? O3 S2 C9 101.89(12) . . ? C7 S2 C9 108.00(13) . . ? 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 C1 C2 0.1(3) . . . . ? C6 N1 C1 C2 -175.06(19) . . . . ? C5 N1 C1 Br1 -179.05(15) . . . . ? C6 N1 C1 Br1 5.8(3) . . . . ? N1 C1 C2 C3 0.3(3) . . . . ? Br1 C1 C2 C3 179.43(16) . . . . ? C1 C2 C3 C4 -0.7(3) . . . . ? C2 C3 C4 C5 0.7(3) . . . . ? C1 N1 C5 C4 0.0(3) . . . . ? C6 N1 C5 C4 175.1(2) . . . . ? C3 C4 C5 N1 -0.4(3) . . . . ? C5 N1 C6 C7 22.1(3) . . . . ? C1 N1 C6 C7 -162.79(19) . . . . ? N1 C6 C7 S1 -98.9(2) . . . . ? N1 C6 C7 S2 83.5(2) . . . . ? C6 C7 S1 O2 166.4(2) . . . . ? S2 C7 S1 O2 -16.1(2) . . . . ? C6 C7 S1 O1 28.9(3) . . . . ? S2 C7 S1 O1 -153.61(18) . . . . ? C6 C7 S1 C8 -79.4(2) . . . . ? S2 C7 S1 C8 98.13(19) . . . . ? F2 C8 S1 O2 -70.70(19) . . . . ? F3 C8 S1 O2 49.23(19) . . . . ? F1 C8 S1 O2 169.51(15) . . . . ? F2 C8 S1 O1 55.94(19) . . . . ? F3 C8 S1 O1 175.87(16) . . . . ? F1 C8 S1 O1 -63.85(18) . . . . ? F2 C8 S1 C7 168.99(17) . . . . ? F3 C8 S1 C7 -71.09(19) . . . . ? F1 C8 S1 C7 49.20(18) . . . . ? C6 C7 S2 O4 -161.8(2) . . . . ? S1 C7 S2 O4 20.6(2) . . . . ? C6 C7 S2 O3 -24.7(2) . . . . ? S1 C7 S2 O3 157.70(17) . . . . ? C6 C7 S2 C9 84.3(2) . . . . ? S1 C7 S2 C9 -93.3(2) . . . . ? F4 C9 S2 O4 -47.7(2) . . . . ? F5 C9 S2 O4 -168.75(17) . . . . ? F6 C9 S2 O4 71.5(2) . . . . ? F4 C9 S2 O3 -173.69(18) . . . . ? F5 C9 S2 O3 65.30(19) . . . . ? F6 C9 S2 O3 -54.5(2) . . . . ? F4 C9 S2 C7 73.9(2) . . . . ? F5 C9 S2 C7 -47.1(2) . . . . ? F6 C9 S2 C7 -166.92(17) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.999 _refine_diff_density_min -0.591 _refine_diff_density_rms 0.112 _database_code_depnum_ccdc_archive 'CCDC 948828' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_CBA09-2j #============================================================================== # 2j #============================================================================== _audit_creation_date '17 January 2013' _audit_creation_method SHELXL-97 #============================================================================== # CHEMICAL DATA #============================================================================== _chemical_name_systematic ; 2-(Quinolin-1-ium-1-yl)-1,1-bis((trifluoromethyl)sulfonyl)ethan-1-ide ; _chemical_name_common ? _chemical_melting_point 470 _chemical_formula_moiety 'C13 H9 F6 N O4 S2' _chemical_formula_sum 'C13 H9 F6 N O4 S2' _chemical_formula_weight 421.33 _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_absolute_configuration . 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #============================================================================== # CRYSTAL DATA #============================================================================== _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c ' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 18.3052(16) _cell_length_b 11.2926(10) _cell_length_c 15.9199(14) _cell_angle_alpha 90.00 _cell_angle_beta 106.7430(10) _cell_angle_gamma 90.00 _cell_volume 3151.3(5) _cell_formula_units_Z 8 _cell_measurement_temperature 90 _cell_measurement_reflns_used 2963 _cell_measurement_theta_min 2.34 _cell_measurement_theta_max 27.58 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.776 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1696 _exptl_absorpt_coefficient_mu 0.426 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.8618 _exptl_absorpt_correction_T_max 0.9159 _exptl_absorpt_process_details ; Crystal Faces plugin in Bruker APEX2 software ; _exptl_special_details ; ? ; #============================================================================== # EXPERIMENTAL DATA #============================================================================== _diffrn_ambient_temperature 90 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker TXS fine-focus rotating anode' _diffrn_radiation_monochromator 'Bruker Helios multilayer confocal mirror' _diffrn_measurement_device_type 'Bruker APEXII CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.333 _diffrn_reflns_number 2771 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0271 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 25.03 _reflns_number_total 2771 _reflns_number_gt 2615 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2006)' _computing_cell_refinement 'APEX2 (Bruker AXS, 2006)' _computing_data_reduction 'SAINT (Bruker AXS, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSHEL (Bruker AXS,2002)' _computing_publication_material 'XCIF (Bruker AXS, 2001)' _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^)+(0.1190P)^2^+3.8675P] 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 2771 _refine_ls_number_parameters 236 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0539 _refine_ls_R_factor_gt 0.0527 _refine_ls_wR_factor_ref 0.1508 _refine_ls_wR_factor_gt 0.1493 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.09456(15) 0.7861(2) 0.15515(18) 0.0154(6) Uani 1 1 d . . . H1 H 0.1387 0.7393 0.1797 0.019 Uiso 1 1 calc R . . C2 C 0.02771(16) 0.7303(2) 0.10608(19) 0.0183(6) Uani 1 1 d . . . H2 H 0.0262 0.6468 0.0984 0.022 Uiso 1 1 calc R . . C3 C -0.03563(15) 0.7980(3) 0.06916(19) 0.0167(6) Uani 1 1 d . . . H3 H -0.0812 0.7615 0.0348 0.020 Uiso 1 1 calc R . . C4 C -0.03338(15) 0.9216(3) 0.08202(16) 0.0129(6) Uani 1 1 d . . . C5 C -0.09711(15) 0.9956(3) 0.04534(17) 0.0147(6) Uani 1 1 d . . . H5 H -0.1428 0.9621 0.0086 0.018 Uiso 1 1 calc R . . C6 C -0.09390(15) 1.1142(3) 0.06198(17) 0.0155(6) Uani 1 1 d . . . H6 H -0.1373 1.1627 0.0377 0.019 Uiso 1 1 calc R . . C7 C -0.02574(15) 1.1647(2) 0.11545(18) 0.0159(6) Uani 1 1 d . . . H7 H -0.0241 1.2474 0.1271 0.019 Uiso 1 1 calc R . . C8 C 0.03845(15) 1.0974(2) 0.15112(17) 0.0135(6) Uani 1 1 d . . . H8 H 0.0840 1.1331 0.1863 0.016 Uiso 1 1 calc R . . C9 C 0.03536(15) 0.9749(2) 0.13452(16) 0.0122(6) Uani 1 1 d . . . C10 C 0.17311(14) 0.9611(2) 0.22127(17) 0.0124(6) Uani 1 1 d . . . H10A H 0.1868 1.0228 0.1842 0.015 Uiso 1 1 calc R . . H10B H 0.1643 1.0012 0.2728 0.015 Uiso 1 1 calc R . . C11 C 0.23882(15) 0.8787(2) 0.25237(17) 0.0122(5) Uani 1 1 d . . . C12 C 0.37189(15) 0.9529(2) 0.20754(18) 0.0156(6) Uani 1 1 d . . . C13 C 0.30429(16) 0.9384(2) 0.43212(18) 0.0159(6) Uani 1 1 d . . . F1 F 0.40695(9) 0.94670(16) 0.14493(11) 0.0222(4) Uani 1 1 d . . . F2 F 0.42340(9) 0.92904(18) 0.28390(11) 0.0270(5) Uani 1 1 d . . . F3 F 0.34771(10) 1.06340(15) 0.21052(12) 0.0253(4) Uani 1 1 d . . . F4 F 0.37634(10) 0.95227(17) 0.43125(12) 0.0295(5) Uani 1 1 d . . . F5 F 0.30476(11) 0.90758(15) 0.51251(10) 0.0253(4) Uani 1 1 d . . . F6 F 0.26903(10) 1.04229(15) 0.41291(11) 0.0247(4) Uani 1 1 d . . . N1 N 0.09836(12) 0.9020(2) 0.16858(14) 0.0114(5) Uani 1 1 d . . . O1 O 0.33010(11) 0.73469(17) 0.20188(13) 0.0175(4) Uani 1 1 d . . . O2 O 0.24769(11) 0.87772(18) 0.09728(12) 0.0170(4) Uani 1 1 d . . . O3 O 0.30910(10) 0.72605(17) 0.37299(12) 0.0158(4) Uani 1 1 d . . . O4 O 0.18343(11) 0.81161(17) 0.37356(13) 0.0167(4) Uani 1 1 d . . . S1 S 0.29187(4) 0.84667(6) 0.18485(4) 0.0113(2) Uani 1 1 d . . . S2 S 0.25525(4) 0.82190(6) 0.35456(4) 0.0114(2) 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 C1 0.0156(13) 0.0123(13) 0.0165(13) 0.0027(10) 0.0015(11) 0.0016(11) C2 0.0185(13) 0.0121(13) 0.0218(15) -0.0007(11) 0.0017(12) -0.0039(11) C3 0.0135(13) 0.0176(14) 0.0174(14) -0.0018(11) 0.0018(11) -0.0034(11) C4 0.0112(13) 0.0183(14) 0.0088(12) 0.0006(10) 0.0027(10) -0.0024(10) C5 0.0116(12) 0.0205(14) 0.0112(12) 0.0014(11) 0.0020(10) -0.0006(11) C6 0.0127(13) 0.0210(14) 0.0117(13) 0.0010(11) 0.0017(10) 0.0053(11) C7 0.0149(14) 0.0160(14) 0.0165(14) -0.0015(11) 0.0040(11) 0.0026(10) C8 0.0111(13) 0.0148(14) 0.0129(13) -0.0014(10) 0.0007(10) -0.0005(10) C9 0.0114(13) 0.0160(14) 0.0083(12) 0.0020(10) 0.0015(10) 0.0004(10) C10 0.0087(12) 0.0114(12) 0.0132(12) -0.0007(10) -0.0027(10) -0.0025(10) C11 0.0111(13) 0.0136(12) 0.0104(12) 0.0019(10) 0.0004(10) 0.0026(10) C12 0.0115(13) 0.0173(14) 0.0165(14) 0.0020(11) 0.0016(11) 0.0002(10) C13 0.0171(14) 0.0153(13) 0.0126(13) -0.0008(10) 0.0001(11) 0.0018(11) F1 0.0163(9) 0.0283(9) 0.0239(9) 0.0043(7) 0.0089(7) 0.0016(7) F2 0.0130(9) 0.0422(11) 0.0197(9) 0.0040(8) -0.0053(7) -0.0057(7) F3 0.0262(10) 0.0138(8) 0.0373(11) -0.0048(7) 0.0110(8) -0.0041(7) F4 0.0193(9) 0.0358(11) 0.0307(10) -0.0136(8) 0.0029(8) -0.0088(7) F5 0.0391(11) 0.0231(9) 0.0106(8) 0.0001(7) 0.0020(7) 0.0001(8) F6 0.0338(10) 0.0131(8) 0.0211(9) -0.0027(7) -0.0017(8) 0.0039(7) N1 0.0099(11) 0.0110(11) 0.0122(11) 0.0014(9) 0.0014(9) -0.0001(8) O1 0.0222(10) 0.0137(10) 0.0174(10) 0.0006(8) 0.0068(8) 0.0039(8) O2 0.0156(10) 0.0227(10) 0.0096(9) 0.0022(8) -0.0013(8) 0.0008(8) O3 0.0192(10) 0.0133(10) 0.0128(9) 0.0021(7) 0.0013(8) 0.0061(8) O4 0.0167(10) 0.0160(10) 0.0187(10) 0.0005(8) 0.0071(8) -0.0009(8) S1 0.0111(4) 0.0114(4) 0.0094(4) 0.0001(2) -0.0003(3) 0.0011(2) S2 0.0129(4) 0.0101(4) 0.0102(4) 0.0007(2) 0.0017(3) 0.0019(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 C1 N1 1.326(4) . ? C1 C2 1.398(4) . ? C1 H1 0.9500 . ? C2 C3 1.372(4) . ? C2 H2 0.9500 . ? C3 C4 1.410(4) . ? C3 H3 0.9500 . ? C4 C5 1.417(4) . ? C4 C9 1.428(4) . ? C5 C6 1.364(4) . ? C5 H5 0.9500 . ? C6 C7 1.412(4) . ? C6 H6 0.9500 . ? C7 C8 1.377(4) . ? C7 H7 0.9500 . ? C8 C9 1.406(4) . ? C8 H8 0.9500 . ? C9 N1 1.393(3) . ? C10 C11 1.488(4) . ? C10 N1 1.536(3) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 S1 1.682(3) . ? C11 S2 1.693(3) . ? C12 F3 1.330(3) . ? C12 F1 1.334(3) . ? C12 F2 1.334(3) . ? C12 S1 1.847(3) . ? C13 F5 1.324(3) . ? C13 F6 1.331(3) . ? C13 F4 1.332(3) . ? C13 S2 1.850(3) . ? O1 S1 1.4329(19) . ? O2 S1 1.4390(19) . ? O3 S2 1.4362(19) . ? O4 S2 1.436(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 N1 C1 C2 122.1(3) . . ? N1 C1 H1 118.9 . . ? C2 C1 H1 118.9 . . ? C3 C2 C1 119.0(3) . . ? C3 C2 H2 120.5 . . ? C1 C2 H2 120.5 . . ? C2 C3 C4 120.3(3) . . ? C2 C3 H3 119.9 . . ? C4 C3 H3 119.9 . . ? C3 C4 C5 122.5(2) . . ? C3 C4 C9 119.1(2) . . ? C5 C4 C9 118.4(3) . . ? C6 C5 C4 121.0(2) . . ? C6 C5 H5 119.5 . . ? C4 C5 H5 119.5 . . ? C5 C6 C7 119.7(2) . . ? C5 C6 H6 120.2 . . ? C7 C6 H6 120.2 . . ? C8 C7 C6 121.7(3) . . ? C8 C7 H7 119.1 . . ? C6 C7 H7 119.1 . . ? C7 C8 C9 118.8(2) . . ? C7 C8 H8 120.6 . . ? C9 C8 H8 120.6 . . ? N1 C9 C8 121.6(2) . . ? N1 C9 C4 118.1(2) . . ? C8 C9 C4 120.4(2) . . ? C11 C10 N1 114.7(2) . . ? C11 C10 H10A 108.6 . . ? N1 C10 H10A 108.6 . . ? C11 C10 H10B 108.6 . . ? N1 C10 H10B 108.6 . . ? H10A C10 H10B 107.6 . . ? C10 C11 S1 118.79(19) . . ? C10 C11 S2 117.35(19) . . ? S1 C11 S2 123.85(16) . . ? F3 C12 F1 108.2(2) . . ? F3 C12 F2 108.2(2) . . ? F1 C12 F2 107.7(2) . . ? F3 C12 S1 111.29(18) . . ? F1 C12 S1 110.19(19) . . ? F2 C12 S1 111.08(19) . . ? F5 C13 F6 108.7(2) . . ? F5 C13 F4 108.1(2) . . ? F6 C13 F4 108.1(2) . . ? F5 C13 S2 108.97(19) . . ? F6 C13 S2 111.31(18) . . ? F4 C13 S2 111.61(19) . . ? C1 N1 C9 121.4(2) . . ? C1 N1 C10 120.9(2) . . ? C9 N1 C10 117.6(2) . . ? O1 S1 O2 120.39(12) . . ? O1 S1 C11 114.15(13) . . ? O2 S1 C11 107.46(12) . . ? O1 S1 C12 102.68(12) . . ? O2 S1 C12 102.94(12) . . ? C11 S1 C12 107.87(13) . . ? O4 S2 O3 120.80(12) . . ? O4 S2 C11 108.24(12) . . ? O3 S2 C11 113.79(12) . . ? O4 S2 C13 102.39(12) . . ? O3 S2 C13 103.12(12) . . ? C11 S2 C13 106.84(13) . . ? 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 N1 C1 C2 C3 1.3(4) . . . . ? C1 C2 C3 C4 -1.1(4) . . . . ? C2 C3 C4 C5 179.9(3) . . . . ? C2 C3 C4 C9 -0.6(4) . . . . ? C3 C4 C5 C6 177.4(3) . . . . ? C9 C4 C5 C6 -2.1(4) . . . . ? C4 C5 C6 C7 1.0(4) . . . . ? C5 C6 C7 C8 0.5(4) . . . . ? C6 C7 C8 C9 -0.8(4) . . . . ? C7 C8 C9 N1 179.9(2) . . . . ? C7 C8 C9 C4 -0.4(4) . . . . ? C3 C4 C9 N1 2.1(4) . . . . ? C5 C4 C9 N1 -178.4(2) . . . . ? C3 C4 C9 C8 -177.7(2) . . . . ? C5 C4 C9 C8 1.8(4) . . . . ? N1 C10 C11 S1 86.0(3) . . . . ? N1 C10 C11 S2 -93.7(2) . . . . ? C2 C1 N1 C9 0.3(4) . . . . ? C2 C1 N1 C10 -178.8(2) . . . . ? C8 C9 N1 C1 177.8(2) . . . . ? C4 C9 N1 C1 -1.9(4) . . . . ? C8 C9 N1 C10 -3.1(3) . . . . ? C4 C9 N1 C10 177.1(2) . . . . ? C11 C10 N1 C1 1.6(3) . . . . ? C11 C10 N1 C9 -177.5(2) . . . . ? C10 C11 S1 O1 -154.50(19) . . . . ? S2 C11 S1 O1 25.2(2) . . . . ? C10 C11 S1 O2 -18.3(2) . . . . ? S2 C11 S1 O2 161.39(17) . . . . ? C10 C11 S1 C12 92.1(2) . . . . ? S2 C11 S1 C12 -88.2(2) . . . . ? F3 C12 S1 O1 -168.71(19) . . . . ? F1 C12 S1 O1 71.2(2) . . . . ? F2 C12 S1 O1 -48.1(2) . . . . ? F3 C12 S1 O2 65.6(2) . . . . ? F1 C12 S1 O2 -54.5(2) . . . . ? F2 C12 S1 O2 -173.79(18) . . . . ? F3 C12 S1 C11 -47.8(2) . . . . ? F1 C12 S1 C11 -167.90(18) . . . . ? F2 C12 S1 C11 72.8(2) . . . . ? C10 C11 S2 O4 30.9(2) . . . . ? S1 C11 S2 O4 -148.81(17) . . . . ? C10 C11 S2 O3 168.11(18) . . . . ? S1 C11 S2 O3 -11.5(2) . . . . ? C10 C11 S2 C13 -78.8(2) . . . . ? S1 C11 S2 C13 101.6(2) . . . . ? F5 C13 S2 O4 54.0(2) . . . . ? F6 C13 S2 O4 -65.9(2) . . . . ? F4 C13 S2 O4 173.24(19) . . . . ? F5 C13 S2 O3 -72.1(2) . . . . ? F6 C13 S2 O3 167.94(19) . . . . ? F4 C13 S2 O3 47.1(2) . . . . ? F5 C13 S2 C11 167.64(18) . . . . ? F6 C13 S2 C11 47.7(2) . . . . ? F4 C13 S2 C11 -73.1(2) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.594 _refine_diff_density_min -0.837 _refine_diff_density_rms 0.130 _database_code_depnum_ccdc_archive 'CCDC 948829' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_CBA09-2k #============================================================================== # 2k #============================================================================== _audit_creation_date '22 February 2013' _audit_creation_method SHELXL-97 #============================================================================== # CHEMICAL DATA #============================================================================== _chemical_name_systematic ; 2-(2-Oxazol-3-ium-3-yl)-1,1-bis((trifluoromethyl)sulfonyl)ethan-1-ide ; _chemical_name_common ? _chemical_melting_point 420 _chemical_formula_moiety 'C7 H5 F6 N O5 S2' _chemical_formula_sum 'C7 H5 F6 N O5 S2' _chemical_formula_weight 361.24 _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_absolute_configuration . 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #============================================================================== # CRYSTAL DATA #============================================================================== _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c ' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 33.764(3) _cell_length_b 8.8317(7) _cell_length_c 20.2876(15) _cell_angle_alpha 90.00 _cell_angle_beta 126.4270(10) _cell_angle_gamma 90.00 _cell_volume 4867.6(6) _cell_formula_units_Z 16 _cell_measurement_temperature 90 _cell_measurement_reflns_used 6282 _cell_measurement_theta_min 2.42 _cell_measurement_theta_max 27.64 _exptl_crystal_description block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.972 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2880 _exptl_absorpt_coefficient_mu 0.539 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.8999 _exptl_absorpt_correction_T_max 0.9382 _exptl_absorpt_process_details ; Crystal Faces plugin in Bruker APEX2 software ; _exptl_special_details ; ? ; #============================================================================== # EXPERIMENTAL DATA #============================================================================== _diffrn_ambient_temperature 90 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker TXS fine-focus rotating anode' _diffrn_radiation_monochromator 'Bruker Helios multilayer confocal mirror' _diffrn_measurement_device_type 'Bruker APEXII CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.333 _diffrn_reflns_number 11425 _diffrn_reflns_av_R_equivalents 0.0206 _diffrn_reflns_av_sigmaI/netI 0.0236 _diffrn_reflns_limit_h_min -40 _diffrn_reflns_limit_h_max 37 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.42 _diffrn_reflns_theta_max 25.03 _reflns_number_total 4293 _reflns_number_gt 3909 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2006)' _computing_cell_refinement 'APEX2 (Bruker AXS, 2006)' _computing_data_reduction 'SAINT (Bruker AXS, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSHEL (Bruker AXS,2002)' _computing_publication_material 'XCIF (Bruker AXS, 2001)' _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^)+(0.0287P)^2^+9.6428P] 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 4293 _refine_ls_number_parameters 379 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0298 _refine_ls_R_factor_gt 0.0266 _refine_ls_wR_factor_ref 0.0673 _refine_ls_wR_factor_gt 0.0652 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _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 C1 C 0.19475(8) 1.0546(2) 0.59777(13) 0.0200(5) Uani 1 1 d . . . H1 H 0.1693 1.0111 0.5986 0.024 Uiso 1 1 calc R . . C2 C 0.25485(7) 1.1966(2) 0.62545(13) 0.0194(4) Uani 1 1 d . . . H2 H 0.2798 1.2721 0.6499 0.023 Uiso 1 1 calc R . . C3 C 0.24502(7) 1.1008(2) 0.56673(13) 0.0185(4) Uani 1 1 d . . . H3 H 0.2612 1.0955 0.5413 0.022 Uiso 1 1 calc R . . C4 C 0.18224(7) 0.8873(2) 0.48568(12) 0.0148(4) Uani 1 1 d . . . H4A H 0.1567 0.9338 0.4321 0.018 Uiso 1 1 calc R . . H4B H 0.2073 0.8414 0.4813 0.018 Uiso 1 1 calc R . . C5 C 0.15904(7) 0.7652(2) 0.50302(11) 0.0116(4) Uani 1 1 d . . . C6 C 0.05961(7) 0.7126(2) 0.36775(12) 0.0184(4) Uani 1 1 d . . . C7 C 0.22043(7) 0.6234(2) 0.65730(12) 0.0168(4) Uani 1 1 d . . . C3B C 1.05445(7) 0.2714(2) 0.44845(12) 0.0150(4) Uani 1 1 d . . . H3B H 1.0730 0.2550 0.4277 0.018 Uiso 1 1 calc R . . O1B O 1.02927(5) 0.35414(16) 0.52025(8) 0.0167(3) Uani 1 1 d . . . C1B C 0.99664(7) 0.2568(2) 0.46557(12) 0.0156(4) Uani 1 1 d . . . H1B H 0.9675 0.2284 0.4594 0.019 Uiso 1 1 calc R . . C4B C 0.98305(7) 0.0868(2) 0.35470(12) 0.0138(4) Uani 1 1 d . . . H4B1 H 0.9940 0.0943 0.3191 0.017 Uiso 1 1 calc R . . H4B2 H 0.9924 -0.0148 0.3803 0.017 Uiso 1 1 calc R . . C5B C 0.92836(7) 0.1010(2) 0.30280(11) 0.0122(4) Uani 1 1 d . . . C6B C 0.87685(7) -0.1731(2) 0.28128(12) 0.0164(4) Uani 1 1 d . . . C7B C 0.89702(7) 0.3971(2) 0.24185(13) 0.0174(4) Uani 1 1 d . . . O4B O 0.85164(5) 0.08552(16) 0.30538(9) 0.0196(3) Uani 1 1 d . . . O3B O 0.93176(5) -0.02861(16) 0.41687(8) 0.0183(3) Uani 1 1 d . . . O6B O 0.84835(5) 0.15821(16) 0.15761(8) 0.0193(3) Uani 1 1 d . . . O5B O 0.93003(5) 0.20913(17) 0.18773(9) 0.0205(3) Uani 1 1 d . . . F1 F 0.06872(5) 0.77977(17) 0.31951(7) 0.0327(3) Uani 1 1 d . . . F2 F 0.01320(4) 0.74059(16) 0.33921(7) 0.0285(3) Uani 1 1 d . . . F3 F 0.06450(4) 0.56456(14) 0.36509(7) 0.0255(3) Uani 1 1 d . . . F4 F 0.18834(4) 0.62919(16) 0.67445(7) 0.0267(3) Uani 1 1 d . . . F5 F 0.25086(4) 0.50872(14) 0.69806(7) 0.0253(3) Uani 1 1 d . . . F6 F 0.24650(5) 0.75151(15) 0.68345(7) 0.0282(3) Uani 1 1 d . . . F7B F 0.85413(4) -0.24796(14) 0.30739(7) 0.0229(3) Uani 1 1 d . . . F8B F 0.91570(4) -0.25422(13) 0.30087(7) 0.0216(3) Uani 1 1 d . . . F9B F 0.84604(4) -0.16178(14) 0.20051(7) 0.0227(3) Uani 1 1 d . . . F10B F 0.87647(5) 0.40641(14) 0.28084(8) 0.0272(3) Uani 1 1 d . . . F11B F 0.94261(4) 0.45234(14) 0.29076(8) 0.0248(3) Uani 1 1 d . . . F12B F 0.87103(4) 0.48262(14) 0.17493(8) 0.0253(3) Uani 1 1 d . . . N1 N 0.20626(6) 1.00980(18) 0.54996(10) 0.0129(3) Uani 1 1 d . . . N1B N 1.00966(6) 0.20449(18) 0.42094(9) 0.0119(3) Uani 1 1 d . . . O1 O 0.22270(5) 1.16755(16) 0.64470(8) 0.0193(3) Uani 1 1 d . . . O2 O 0.09014(5) 0.94906(16) 0.45919(8) 0.0173(3) Uani 1 1 d . . . O3 O 0.08896(5) 0.70261(15) 0.51782(8) 0.0146(3) Uani 1 1 d . . . O4 O 0.22977(5) 0.58900(16) 0.54087(8) 0.0183(3) Uani 1 1 d . . . O5 O 0.15742(5) 0.47382(15) 0.52511(8) 0.0172(3) Uani 1 1 d . . . C2B C 1.06598(7) 0.3628(2) 0.50956(12) 0.0168(4) Uani 1 1 d . . . H2B H 1.0947 0.4239 0.5407 0.020 Uiso 1 1 calc R . . S1 S 0.100974(16) 0.78950(5) 0.47209(3) 0.01112(11) Uani 1 1 d . . . S2 S 0.189320(17) 0.60075(5) 0.54644(3) 0.01188(11) Uani 1 1 d . . . S3 S 0.896969(17) 0.01319(5) 0.33229(3) 0.01278(11) Uani 1 1 d . . . S4 S 0.899144(17) 0.19948(5) 0.21451(3) 0.01322(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 C1 0.0197(11) 0.0245(12) 0.0222(11) -0.0053(9) 0.0159(9) -0.0071(9) C2 0.0161(10) 0.0182(11) 0.0288(11) -0.0017(9) 0.0160(9) -0.0034(8) C3 0.0183(10) 0.0161(11) 0.0288(12) -0.0012(9) 0.0182(10) -0.0029(8) C4 0.0168(10) 0.0173(10) 0.0133(10) -0.0032(8) 0.0105(8) -0.0022(8) C5 0.0089(9) 0.0146(10) 0.0123(9) 0.0000(7) 0.0069(8) 0.0004(7) C6 0.0127(10) 0.0261(12) 0.0149(10) -0.0008(8) 0.0075(9) 0.0011(8) C7 0.0137(10) 0.0188(11) 0.0161(10) 0.0013(8) 0.0078(9) 0.0053(8) C3B 0.0134(10) 0.0144(10) 0.0201(10) 0.0028(8) 0.0115(9) -0.0002(8) O1B 0.0159(7) 0.0175(7) 0.0191(7) -0.0033(6) 0.0117(6) -0.0016(6) C1B 0.0141(10) 0.0164(10) 0.0178(10) -0.0007(8) 0.0103(9) -0.0001(8) C4B 0.0127(9) 0.0146(10) 0.0166(10) -0.0023(8) 0.0101(8) 0.0007(8) C5B 0.0112(9) 0.0127(10) 0.0146(10) -0.0006(8) 0.0088(8) 0.0000(7) C6B 0.0175(10) 0.0142(10) 0.0188(10) 0.0001(8) 0.0114(9) -0.0012(8) C7B 0.0182(10) 0.0152(10) 0.0220(11) 0.0022(8) 0.0136(9) 0.0013(8) O4B 0.0173(7) 0.0188(8) 0.0306(8) -0.0037(6) 0.0186(7) -0.0012(6) O3B 0.0237(8) 0.0182(8) 0.0167(7) -0.0016(6) 0.0140(6) -0.0034(6) O6B 0.0151(7) 0.0205(8) 0.0165(7) -0.0008(6) 0.0062(6) 0.0009(6) O5B 0.0241(8) 0.0244(8) 0.0207(7) 0.0035(6) 0.0176(7) 0.0038(6) F1 0.0315(7) 0.0507(9) 0.0135(6) 0.0007(6) 0.0120(6) -0.0085(6) F2 0.0090(6) 0.0408(8) 0.0239(7) -0.0079(6) 0.0034(5) 0.0024(5) F3 0.0226(6) 0.0274(7) 0.0221(6) -0.0110(5) 0.0108(6) -0.0010(5) F4 0.0239(7) 0.0441(8) 0.0184(6) 0.0050(6) 0.0159(6) 0.0110(6) F5 0.0242(7) 0.0272(7) 0.0173(6) 0.0059(5) 0.0083(5) 0.0149(5) F6 0.0283(7) 0.0260(7) 0.0168(6) -0.0041(5) 0.0060(6) -0.0046(6) F7B 0.0250(7) 0.0200(6) 0.0283(7) -0.0010(5) 0.0183(6) -0.0082(5) F8B 0.0229(6) 0.0162(6) 0.0285(7) -0.0023(5) 0.0168(6) 0.0021(5) F9B 0.0247(7) 0.0212(6) 0.0165(6) -0.0032(5) 0.0092(5) -0.0044(5) F10B 0.0398(8) 0.0183(7) 0.0411(8) -0.0012(6) 0.0337(7) 0.0029(6) F11B 0.0214(6) 0.0165(6) 0.0301(7) -0.0032(5) 0.0119(6) -0.0028(5) F12B 0.0251(7) 0.0190(6) 0.0294(7) 0.0090(5) 0.0150(6) 0.0054(5) N1 0.0125(8) 0.0144(8) 0.0143(8) 0.0011(7) 0.0093(7) -0.0001(6) N1B 0.0111(8) 0.0130(8) 0.0129(8) 0.0020(6) 0.0079(7) 0.0021(6) O1 0.0205(7) 0.0210(8) 0.0210(7) -0.0074(6) 0.0148(7) -0.0065(6) O2 0.0152(7) 0.0167(7) 0.0205(7) 0.0037(6) 0.0108(6) 0.0050(6) O3 0.0125(7) 0.0173(7) 0.0185(7) 0.0000(6) 0.0116(6) -0.0002(5) O4 0.0138(7) 0.0240(8) 0.0216(7) -0.0004(6) 0.0129(6) 0.0040(6) O5 0.0163(7) 0.0140(7) 0.0210(7) -0.0002(6) 0.0109(6) 0.0002(6) C2B 0.0134(10) 0.0166(10) 0.0222(11) 0.0030(8) 0.0116(9) -0.0016(8) S1 0.0086(2) 0.0141(2) 0.0112(2) -0.00029(18) 0.00614(19) 0.00110(18) S2 0.0098(2) 0.0146(2) 0.0126(2) -0.00037(18) 0.0074(2) 0.00174(18) S3 0.0138(2) 0.0125(2) 0.0166(2) -0.00192(18) 0.0115(2) -0.00159(18) S4 0.0140(2) 0.0135(2) 0.0141(2) 0.00036(18) 0.0094(2) 0.00119(19) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.302(3) . ? C1 O1 1.313(3) . ? C1 H1 0.9500 . ? C2 C3 1.333(3) . ? C2 O1 1.379(2) . ? C2 H2 0.9500 . ? C3 N1 1.395(2) . ? C3 H3 0.9500 . ? C4 C5 1.492(3) . ? C4 N1 1.508(2) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 S1 1.6799(18) . ? C5 S2 1.6917(19) . ? C6 F3 1.323(2) . ? C6 F1 1.327(2) . ? C6 F2 1.332(2) . ? C6 S1 1.839(2) . ? C7 F4 1.321(2) . ? C7 F5 1.325(2) . ? C7 F6 1.335(2) . ? C7 S2 1.843(2) . ? C3B C2B 1.329(3) . ? C3B N1B 1.395(2) . ? C3B H3B 0.9500 . ? O1B C1B 1.316(2) . ? O1B C2B 1.382(2) . ? C1B N1B 1.304(2) . ? C1B H1B 0.9500 . ? C4B C5B 1.492(3) . ? C4B N1B 1.503(2) . ? C4B H4B1 0.9900 . ? C4B H4B2 0.9900 . ? C5B S3 1.6840(19) . ? C5B S4 1.6849(19) . ? C6B F9B 1.324(2) . ? C6B F8B 1.331(2) . ? C6B F7B 1.337(2) . ? C6B S3 1.845(2) . ? C7B F10B 1.329(2) . ? C7B F12B 1.330(2) . ? C7B F11B 1.333(2) . ? C7B S4 1.845(2) . ? O4B S3 1.4339(14) . ? O3B S3 1.4376(15) . ? O6B S4 1.4336(14) . ? O5B S4 1.4362(14) . ? O2 S1 1.4403(15) . ? O3 S1 1.4356(14) . ? O4 S2 1.4394(14) . ? O5 S2 1.4319(14) . ? C2B H2B 0.9500 . ? 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 C1 O1 111.54(17) . . ? N1 C1 H1 124.2 . . ? O1 C1 H1 124.2 . . ? C3 C2 O1 108.34(17) . . ? C3 C2 H2 125.8 . . ? O1 C2 H2 125.8 . . ? C2 C3 N1 106.49(17) . . ? C2 C3 H3 126.8 . . ? N1 C3 H3 126.8 . . ? C5 C4 N1 113.74(15) . . ? C5 C4 H4A 108.8 . . ? N1 C4 H4A 108.8 . . ? C5 C4 H4B 108.8 . . ? N1 C4 H4B 108.8 . . ? H4A C4 H4B 107.7 . . ? C4 C5 S1 118.64(14) . . ? C4 C5 S2 120.23(14) . . ? S1 C5 S2 120.96(11) . . ? F3 C6 F1 108.81(17) . . ? F3 C6 F2 107.98(17) . . ? F1 C6 F2 108.93(17) . . ? F3 C6 S1 112.59(14) . . ? F1 C6 S1 109.49(14) . . ? F2 C6 S1 108.98(13) . . ? F4 C7 F5 108.58(16) . . ? F4 C7 F6 108.23(16) . . ? F5 C7 F6 108.41(16) . . ? F4 C7 S2 111.31(13) . . ? F5 C7 S2 110.33(13) . . ? F6 C7 S2 109.90(14) . . ? C2B C3B N1B 106.14(17) . . ? C2B C3B H3B 126.9 . . ? N1B C3B H3B 126.9 . . ? C1B O1B C2B 106.49(15) . . ? N1B C1B O1B 110.99(17) . . ? N1B C1B H1B 124.5 . . ? O1B C1B H1B 124.5 . . ? C5B C4B N1B 113.89(15) . . ? C5B C4B H4B1 108.8 . . ? N1B C4B H4B1 108.8 . . ? C5B C4B H4B2 108.8 . . ? N1B C4B H4B2 108.8 . . ? H4B1 C4B H4B2 107.7 . . ? C4B C5B S3 119.13(14) . . ? C4B C5B S4 119.45(14) . . ? S3 C5B S4 121.39(11) . . ? F9B C6B F8B 108.72(16) . . ? F9B C6B F7B 108.29(16) . . ? F8B C6B F7B 108.14(16) . . ? F9B C6B S3 112.55(14) . . ? F8B C6B S3 110.05(13) . . ? F7B C6B S3 108.98(13) . . ? F10B C7B F12B 108.13(16) . . ? F10B C7B F11B 108.32(17) . . ? F12B C7B F11B 108.77(16) . . ? F10B C7B S4 111.40(13) . . ? F12B C7B S4 110.50(14) . . ? F11B C7B S4 109.64(13) . . ? C1 N1 C3 107.14(17) . . ? C1 N1 C4 128.12(16) . . ? C3 N1 C4 124.71(16) . . ? C1B N1B C3B 107.74(16) . . ? C1B N1B C4B 126.65(16) . . ? C3B N1B C4B 125.53(15) . . ? C1 O1 C2 106.49(16) . . ? C3B C2B O1B 108.64(17) . . ? C3B C2B H2B 125.7 . . ? O1B C2B H2B 125.7 . . ? O3 S1 O2 120.12(8) . . ? O3 S1 C5 113.90(9) . . ? O2 S1 C5 107.86(9) . . ? O3 S1 C6 103.51(9) . . ? O2 S1 C6 102.40(9) . . ? C5 S1 C6 107.64(9) . . ? O5 S2 O4 119.89(8) . . ? O5 S2 C5 113.66(9) . . ? O4 S2 C5 109.23(9) . . ? O5 S2 C7 103.59(9) . . ? O4 S2 C7 102.94(8) . . ? C5 S2 C7 105.81(9) . . ? O4B S3 O3B 119.98(9) . . ? O4B S3 C5B 114.46(9) . . ? O3B S3 C5B 107.56(9) . . ? O4B S3 C6B 103.27(9) . . ? O3B S3 C6B 102.01(9) . . ? C5B S3 C6B 108.15(9) . . ? O6B S4 O5B 120.04(9) . . ? O6B S4 C5B 112.96(9) . . ? O5B S4 C5B 109.55(9) . . ? O6B S4 C7B 103.95(9) . . ? O5B S4 C7B 102.95(9) . . ? C5B S4 C7B 105.72(9) . . ? 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 O1 C2 C3 N1 -0.5(2) . . . . ? N1 C4 C5 S1 86.26(19) . . . . ? N1 C4 C5 S2 -98.35(18) . . . . ? C2B O1B C1B N1B -0.5(2) . . . . ? N1B C4B C5B S3 -87.99(19) . . . . ? N1B C4B C5B S4 94.06(18) . . . . ? O1 C1 N1 C3 0.0(2) . . . . ? O1 C1 N1 C4 -178.03(17) . . . . ? C2 C3 N1 C1 0.4(2) . . . . ? C2 C3 N1 C4 178.44(18) . . . . ? C5 C4 N1 C1 -28.1(3) . . . . ? C5 C4 N1 C3 154.18(18) . . . . ? O1B C1B N1B C3B 0.4(2) . . . . ? O1B C1B N1B C4B 177.31(16) . . . . ? C2B C3B N1B C1B -0.1(2) . . . . ? C2B C3B N1B C4B -177.09(17) . . . . ? C5B C4B N1B C1B 39.2(3) . . . . ? C5B C4B N1B C3B -144.40(18) . . . . ? N1 C1 O1 C2 -0.3(2) . . . . ? C3 C2 O1 C1 0.5(2) . . . . ? N1B C3B C2B O1B -0.1(2) . . . . ? C1B O1B C2B C3B 0.4(2) . . . . ? C4 C5 S1 O3 -156.11(14) . . . . ? S2 C5 S1 O3 28.54(15) . . . . ? C4 C5 S1 O2 -20.09(17) . . . . ? S2 C5 S1 O2 164.56(11) . . . . ? C4 C5 S1 C6 89.75(16) . . . . ? S2 C5 S1 C6 -85.60(14) . . . . ? F3 C6 S1 O3 -56.03(15) . . . . ? F1 C6 S1 O3 -177.20(13) . . . . ? F2 C6 S1 O3 63.75(16) . . . . ? F3 C6 S1 O2 178.43(13) . . . . ? F1 C6 S1 O2 57.26(15) . . . . ? F2 C6 S1 O2 -61.79(16) . . . . ? F3 C6 S1 C5 64.88(16) . . . . ? F1 C6 S1 C5 -56.29(16) . . . . ? F2 C6 S1 C5 -175.34(14) . . . . ? C4 C5 S2 O5 -151.91(14) . . . . ? S1 C5 S2 O5 23.36(15) . . . . ? C4 C5 S2 O4 -15.11(18) . . . . ? S1 C5 S2 O4 160.16(11) . . . . ? C4 C5 S2 C7 95.08(16) . . . . ? S1 C5 S2 C7 -89.64(13) . . . . ? F4 C7 S2 O5 -51.57(16) . . . . ? F5 C7 S2 O5 69.04(15) . . . . ? F6 C7 S2 O5 -171.47(13) . . . . ? F4 C7 S2 O4 -177.13(14) . . . . ? F5 C7 S2 O4 -56.51(16) . . . . ? F6 C7 S2 O4 62.98(15) . . . . ? F4 C7 S2 C5 68.27(16) . . . . ? F5 C7 S2 C5 -171.11(14) . . . . ? F6 C7 S2 C5 -51.62(15) . . . . ? C4B C5B S3 O4B 151.49(14) . . . . ? S4 C5B S3 O4B -30.60(16) . . . . ? C4B C5B S3 O3B 15.46(17) . . . . ? S4 C5B S3 O3B -166.64(11) . . . . ? C4B C5B S3 C6B -94.02(16) . . . . ? S4 C5B S3 C6B 83.88(14) . . . . ? F9B C6B S3 O4B 58.51(15) . . . . ? F8B C6B S3 O4B 179.95(13) . . . . ? F7B C6B S3 O4B -61.63(15) . . . . ? F9B C6B S3 O3B -176.38(13) . . . . ? F8B C6B S3 O3B -54.95(14) . . . . ? F7B C6B S3 O3B 63.48(14) . . . . ? F9B C6B S3 C5B -63.15(16) . . . . ? F8B C6B S3 C5B 58.28(15) . . . . ? F7B C6B S3 C5B 176.71(13) . . . . ? C4B C5B S4 O6B 157.85(14) . . . . ? S3 C5B S4 O6B -20.04(16) . . . . ? C4B C5B S4 O5B 21.19(18) . . . . ? S3 C5B S4 O5B -156.70(11) . . . . ? C4B C5B S4 C7B -89.11(16) . . . . ? S3 C5B S4 C7B 92.99(13) . . . . ? F10B C7B S4 O6B 64.38(16) . . . . ? F12B C7B S4 O6B -55.84(15) . . . . ? F11B C7B S4 O6B -175.72(13) . . . . ? F10B C7B S4 O5B -169.72(14) . . . . ? F12B C7B S4 O5B 70.06(15) . . . . ? F11B C7B S4 O5B -49.82(15) . . . . ? F10B C7B S4 C5B -54.79(16) . . . . ? F12B C7B S4 C5B -175.01(13) . . . . ? F11B C7B S4 C5B 65.10(15) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.567 _refine_diff_density_min -0.351 _refine_diff_density_rms 0.057 _database_code_depnum_ccdc_archive 'CCDC 948830' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_CBA09-2m #============================================================================== # 2m #============================================================================== _audit_creation_date '22 Januray 2013' _audit_creation_method SHELXL-97 #============================================================================== # CHEMICAL DATA #============================================================================== _chemical_name_systematic ; 2-(1-Methyl-1H-imidazol-3-ium-3-yl)-1,1-bis((trifluoromethyl)sulfonyl)ethan -1-ide ; _chemical_name_common ? _chemical_melting_point 466 _chemical_formula_moiety 'C8 H8 F6 N2 O4 S2' _chemical_formula_sum 'C8 H8 F6 N2 O4 S2' _chemical_formula_weight 374.28 _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_absolute_configuration unk 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #============================================================================== # CRYSTAL DATA #============================================================================== _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C c ' _symmetry_space_group_name_Hall 'C -2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 14.813(3) _cell_length_b 10.590(2) _cell_length_c 10.069(2) _cell_angle_alpha 90.00 _cell_angle_beta 120.578(3) _cell_angle_gamma 90.00 _cell_volume 1359.9(5) _cell_formula_units_Z 4 _cell_measurement_temperature 90 _cell_measurement_reflns_used 2611 _cell_measurement_theta_min 2.50 _cell_measurement_theta_max 27.61 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.828 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_absorpt_coefficient_mu 0.482 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.9140 _exptl_absorpt_correction_T_max 0.9444 _exptl_absorpt_process_details ; Crystal Faces plugin in Bruker APEX2 software ; _exptl_special_details ; ? ; #============================================================================== # EXPERIMENTAL DATA #============================================================================== _diffrn_ambient_temperature 90 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker TXS fine-focus rotating anode' _diffrn_radiation_monochromator 'Bruker Helios multilayer confocal mirror' _diffrn_measurement_device_type 'Bruker APEXII CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.333 _diffrn_reflns_number 3133 _diffrn_reflns_av_R_equivalents 0.0146 _diffrn_reflns_av_sigmaI/netI 0.0210 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.50 _diffrn_reflns_theta_max 25.01 _reflns_number_total 1717 _reflns_number_gt 1690 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2006)' _computing_cell_refinement 'APEX2 (Bruker AXS, 2006)' _computing_data_reduction 'SAINT (Bruker AXS, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSHEL (Bruker AXS,2002)' _computing_publication_material 'XCIF (Bruker AXS, 2001)' _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^)+(0.0252P)^2^+1.1742P] 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 0.18(6) _refine_ls_number_reflns 1717 _refine_ls_number_parameters 200 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0213 _refine_ls_R_factor_gt 0.0207 _refine_ls_wR_factor_ref 0.0517 _refine_ls_wR_factor_gt 0.0513 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.050 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.23364(18) 0.4883(2) 0.9896(3) 0.0143(5) Uani 1 1 d . . . H1 H 0.2723 0.5243 1.0898 0.017 Uiso 1 1 calc R . . C2 C 0.1266(2) 0.4658(2) 0.7399(3) 0.0162(5) Uani 1 1 d . . . H2 H 0.0774 0.4842 0.6349 0.019 Uiso 1 1 calc R . . C3 C 0.16962(19) 0.3523(2) 0.7983(3) 0.0162(5) Uani 1 1 d . . . H3 H 0.1562 0.2758 0.7421 0.019 Uiso 1 1 calc R . . C4 C 0.14718(19) 0.6890(2) 0.8533(3) 0.0164(5) Uani 1 1 d . . . H4A H 0.1920 0.7325 0.8209 0.020 Uiso 1 1 calc R . . H4B H 0.1676 0.7197 0.9578 0.020 Uiso 1 1 calc R . . C5 C 0.03526(19) 0.7239(2) 0.7445(3) 0.0136(5) Uani 1 1 d . . . C6 C -0.1227(2) 0.5727(3) 0.7488(3) 0.0219(6) Uani 1 1 d . . . C7 C 0.0306(2) 0.9456(3) 0.5823(3) 0.0282(7) Uani 1 1 d . . . C8 C 0.2999(2) 0.2686(2) 1.0646(3) 0.0196(6) Uani 1 1 d . . . H8A H 0.3281 0.2998 1.1701 0.029 Uiso 1 1 calc R . . H8B H 0.3578 0.2454 1.0489 0.029 Uiso 1 1 calc R . . H8C H 0.2559 0.1943 1.0483 0.029 Uiso 1 1 calc R . . F1 F -0.18294(15) 0.56237(16) 0.59703(19) 0.0375(5) Uani 1 1 d . . . F2 F -0.18330(14) 0.56478(16) 0.8110(2) 0.0366(5) Uani 1 1 d . . . F3 F -0.05686(15) 0.47550(13) 0.7996(2) 0.0360(4) Uani 1 1 d . . . F4 F -0.03357(14) 1.01254(15) 0.6106(2) 0.0317(4) Uani 1 1 d . . . F5 F 0.0215(2) 0.98546(18) 0.4512(3) 0.0600(7) Uani 1 1 d . . . F6 F 0.12745(15) 0.96648(17) 0.6952(3) 0.0584(6) Uani 1 1 d . . . N1 N 0.16751(16) 0.55023(18) 0.8610(2) 0.0135(4) Uani 1 1 d . . . N2 N 0.23667(17) 0.36770(17) 0.9547(2) 0.0132(4) Uani 1 1 d . . . O1 O -0.13461(14) 0.81368(16) 0.7316(2) 0.0186(4) Uani 1 1 d . . . O2 O 0.00542(15) 0.71427(16) 0.9718(2) 0.0216(4) Uani 1 1 d . . . O3 O -0.11043(15) 0.77088(18) 0.4599(2) 0.0236(4) Uani 1 1 d . . . O4 O 0.07298(15) 0.72439(18) 0.5249(2) 0.0260(5) Uani 1 1 d . . . S1 S -0.05119(4) 0.72370(5) 0.80645(6) 0.01267(14) Uani 1 1 d . . . S2 S 0.00061(5) 0.77507(6) 0.56625(6) 0.01604(15) 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 C1 0.0095(13) 0.0188(12) 0.0128(12) -0.0026(9) 0.0044(11) 0.0003(10) C2 0.0142(12) 0.0194(13) 0.0121(12) -0.0027(10) 0.0046(10) 0.0015(11) C3 0.0145(13) 0.0178(13) 0.0144(13) -0.0036(9) 0.0060(11) 0.0012(10) C4 0.0097(13) 0.0155(12) 0.0178(12) -0.0028(9) 0.0024(11) -0.0001(10) C5 0.0116(13) 0.0123(11) 0.0161(12) 0.0007(9) 0.0065(11) 0.0003(10) C6 0.0207(14) 0.0187(13) 0.0292(15) 0.0017(11) 0.0147(13) -0.0006(12) C7 0.0269(18) 0.0232(15) 0.0434(18) 0.0109(13) 0.0243(16) 0.0057(13) C8 0.0194(14) 0.0198(13) 0.0171(13) 0.0041(10) 0.0074(12) 0.0047(11) F1 0.0394(11) 0.0320(9) 0.0269(9) -0.0101(7) 0.0065(8) -0.0186(8) F2 0.0330(11) 0.0357(10) 0.0560(12) -0.0031(8) 0.0336(10) -0.0104(8) F3 0.0317(10) 0.0130(8) 0.0659(12) 0.0046(8) 0.0267(9) 0.0020(8) F4 0.0326(10) 0.0202(8) 0.0501(11) 0.0023(7) 0.0268(9) 0.0030(7) F5 0.103(2) 0.0380(11) 0.0809(16) 0.0317(10) 0.0771(16) 0.0226(12) F6 0.0207(10) 0.0261(10) 0.1045(18) 0.0085(11) 0.0145(11) -0.0084(8) N1 0.0090(10) 0.0151(10) 0.0134(10) -0.0002(8) 0.0034(9) 0.0002(9) N2 0.0108(11) 0.0136(9) 0.0152(10) 0.0010(8) 0.0067(9) 0.0001(9) O1 0.0157(9) 0.0193(9) 0.0216(9) 0.0038(7) 0.0101(8) 0.0051(8) O2 0.0219(10) 0.0259(10) 0.0151(9) 0.0027(7) 0.0080(8) 0.0044(8) O3 0.0161(10) 0.0363(11) 0.0156(9) 0.0038(8) 0.0061(8) 0.0030(8) O4 0.0251(11) 0.0326(11) 0.0274(11) 0.0042(8) 0.0187(9) 0.0077(9) S1 0.0117(3) 0.0128(3) 0.0130(3) 0.0012(2) 0.0058(2) 0.0013(3) S2 0.0131(3) 0.0197(3) 0.0162(3) 0.0029(3) 0.0081(3) 0.0023(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N2 1.332(3) . ? C1 N1 1.333(3) . ? C1 H1 0.9500 . ? C2 C3 1.347(3) . ? C2 N1 1.379(3) . ? C2 H2 0.9500 . ? C3 N2 1.379(3) . ? C3 H3 0.9500 . ? C4 N1 1.495(3) . ? C4 C5 1.496(3) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 S2 1.686(2) . ? C5 S1 1.686(3) . ? C6 F1 1.325(3) . ? C6 F3 1.328(3) . ? C6 F2 1.334(3) . ? C6 S1 1.842(3) . ? C7 F6 1.319(4) . ? C7 F5 1.325(3) . ? C7 F4 1.328(3) . ? C7 S2 1.847(3) . ? C8 N2 1.466(3) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? O1 S1 1.4337(19) . ? O2 S1 1.4365(19) . ? O3 S2 1.436(2) . ? O4 S2 1.437(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 N2 C1 N1 108.8(2) . . ? N2 C1 H1 125.6 . . ? N1 C1 H1 125.6 . . ? C3 C2 N1 107.1(2) . . ? C3 C2 H2 126.4 . . ? N1 C2 H2 126.4 . . ? C2 C3 N2 107.4(2) . . ? C2 C3 H3 126.3 . . ? N2 C3 H3 126.3 . . ? N1 C4 C5 113.6(2) . . ? N1 C4 H4A 108.9 . . ? C5 C4 H4A 108.9 . . ? N1 C4 H4B 108.9 . . ? C5 C4 H4B 108.9 . . ? H4A C4 H4B 107.7 . . ? C4 C5 S2 118.87(19) . . ? C4 C5 S1 119.77(18) . . ? S2 C5 S1 121.15(15) . . ? F1 C6 F3 108.2(2) . . ? F1 C6 F2 108.5(2) . . ? F3 C6 F2 108.0(2) . . ? F1 C6 S1 112.16(18) . . ? F3 C6 S1 111.1(2) . . ? F2 C6 S1 108.83(18) . . ? F6 C7 F5 108.7(3) . . ? F6 C7 F4 108.0(3) . . ? F5 C7 F4 108.8(2) . . ? F6 C7 S2 110.30(19) . . ? F5 C7 S2 109.0(2) . . ? F4 C7 S2 111.96(19) . . ? N2 C8 H8A 109.5 . . ? N2 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N2 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C1 N1 C2 108.39(19) . . ? C1 N1 C4 124.3(2) . . ? C2 N1 C4 127.3(2) . . ? C1 N2 C3 108.27(19) . . ? C1 N2 C8 125.6(2) . . ? C3 N2 C8 126.2(2) . . ? O1 S1 O2 119.64(10) . . ? O1 S1 C5 114.73(11) . . ? O2 S1 C5 108.85(12) . . ? O1 S1 C6 102.00(12) . . ? O2 S1 C6 102.02(11) . . ? C5 S1 C6 107.92(12) . . ? O3 S2 O4 120.84(12) . . ? O3 S2 C5 113.39(12) . . ? O4 S2 C5 108.70(12) . . ? O3 S2 C7 103.22(12) . . ? O4 S2 C7 102.05(12) . . ? C5 S2 C7 106.97(12) . . ? 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 N1 C2 C3 N2 -0.1(3) . . . . ? N1 C4 C5 S2 -98.8(2) . . . . ? N1 C4 C5 S1 86.6(2) . . . . ? N2 C1 N1 C2 0.3(3) . . . . ? N2 C1 N1 C4 -177.2(2) . . . . ? C3 C2 N1 C1 -0.1(3) . . . . ? C3 C2 N1 C4 177.2(2) . . . . ? C5 C4 N1 C1 -142.5(2) . . . . ? C5 C4 N1 C2 40.5(3) . . . . ? N1 C1 N2 C3 -0.3(3) . . . . ? N1 C1 N2 C8 -179.8(2) . . . . ? C2 C3 N2 C1 0.2(3) . . . . ? C2 C3 N2 C8 179.7(2) . . . . ? C4 C5 S1 O1 149.48(18) . . . . ? S2 C5 S1 O1 -25.1(2) . . . . ? C4 C5 S1 O2 12.4(2) . . . . ? S2 C5 S1 O2 -162.18(14) . . . . ? C4 C5 S1 C6 -97.6(2) . . . . ? S2 C5 S1 C6 87.85(17) . . . . ? F1 C6 S1 O1 54.6(2) . . . . ? F3 C6 S1 O1 175.81(18) . . . . ? F2 C6 S1 O1 -65.5(2) . . . . ? F1 C6 S1 O2 178.8(2) . . . . ? F3 C6 S1 O2 -60.0(2) . . . . ? F2 C6 S1 O2 58.7(2) . . . . ? F1 C6 S1 C5 -66.6(2) . . . . ? F3 C6 S1 C5 54.6(2) . . . . ? F2 C6 S1 C5 173.32(18) . . . . ? C4 C5 S2 O3 163.15(17) . . . . ? S1 C5 S2 O3 -22.3(2) . . . . ? C4 C5 S2 O4 25.8(2) . . . . ? S1 C5 S2 O4 -159.65(14) . . . . ? C4 C5 S2 C7 -83.7(2) . . . . ? S1 C5 S2 C7 90.85(17) . . . . ? F6 C7 S2 O3 170.1(2) . . . . ? F5 C7 S2 O3 -70.7(2) . . . . ? F4 C7 S2 O3 49.8(2) . . . . ? F6 C7 S2 O4 -63.8(2) . . . . ? F5 C7 S2 O4 55.4(2) . . . . ? F4 C7 S2 O4 175.87(19) . . . . ? F6 C7 S2 C5 50.2(2) . . . . ? F5 C7 S2 C5 169.5(2) . . . . ? F4 C7 S2 C5 -70.1(2) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.297 _refine_diff_density_min -0.245 _refine_diff_density_rms 0.040 _database_code_depnum_ccdc_archive 'CCDC 948831' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_CBA09-2n #============================================================================== # 2n #============================================================================== _audit_creation_date '20 February 2013' _audit_creation_method SHELXL-97 #============================================================================== # CHEMICAL DATA #============================================================================== _chemical_name_systematic ; 2-(1-Butyl-1H-imidazol-3-ium-3-yl)-1,1-bis((trifluoromethyl)sulfonyl)ethan-1-ide ; _chemical_name_common ? _chemical_melting_point 415 _chemical_formula_moiety 'C11 H14 F6 N2 O4 S2' _chemical_formula_sum 'C11 H14 F6 N2 O4 S2' _chemical_formula_weight 416.36 _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_absolute_configuration . 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #============================================================================== # CRYSTAL DATA #============================================================================== _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 11.1898(14) _cell_length_b 12.4495(15) _cell_length_c 12.4571(15) _cell_angle_alpha 90.00 _cell_angle_beta 107.577(2) _cell_angle_gamma 90.00 _cell_volume 1654.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 90 _cell_measurement_reflns_used 5265 _cell_measurement_theta_min 2.37 _cell_measurement_theta_max 27.62 _exptl_crystal_description Block _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.672 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 848 _exptl_absorpt_coefficient_mu 0.406 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.8846 _exptl_absorpt_correction_T_max 0.9454 _exptl_absorpt_process_details ; Crystal Faces plugin in Bruker APEX2 software ; _exptl_special_details ; ? ; #============================================================================== # EXPERIMENTAL DATA #============================================================================== _diffrn_ambient_temperature 90 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker TXS fine-focus rotating anode' _diffrn_radiation_monochromator 'Bruker Helios multilayer confocal mirror' _diffrn_measurement_device_type 'Bruker APEXII CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.333 _diffrn_reflns_number 7856 _diffrn_reflns_av_R_equivalents 0.0165 _diffrn_reflns_av_sigmaI/netI 0.0186 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.37 _diffrn_reflns_theta_max 25.02 _reflns_number_total 2921 _reflns_number_gt 2716 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2006)' _computing_cell_refinement 'APEX2 (Bruker AXS, 2006)' _computing_data_reduction 'SAINT (Bruker AXS, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSHEL (Bruker AXS,2002)' _computing_publication_material 'XCIF (Bruker AXS, 2001)' _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^)+(0.0389P)^2^+1.4223P] 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 2921 _refine_ls_number_parameters 227 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0310 _refine_ls_R_factor_gt 0.0288 _refine_ls_wR_factor_ref 0.0754 _refine_ls_wR_factor_gt 0.0738 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.006 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.26896(16) 0.52123(13) -0.15567(13) 0.0140(3) Uani 1 1 d . . . H1 H 0.3573 0.5230 -0.1413 0.017 Uiso 1 1 calc R . . C2 C 0.07096(16) 0.56995(14) -0.20092(15) 0.0184(4) Uani 1 1 d . . . H2 H -0.0030 0.6124 -0.2242 0.022 Uiso 1 1 calc R . . C3 C 0.07809(16) 0.46518(14) -0.17192(14) 0.0181(4) Uani 1 1 d . . . H3 H 0.0101 0.4200 -0.1707 0.022 Uiso 1 1 calc R . . C4 C 0.25584(16) 0.32950(13) -0.10165(13) 0.0147(3) Uani 1 1 d . . . H4A H 0.3440 0.3264 -0.1024 0.018 Uiso 1 1 calc R . . H4B H 0.2086 0.2729 -0.1529 0.018 Uiso 1 1 calc R . . C5 C 0.25155(15) 0.30686(13) 0.01567(13) 0.0135(3) Uani 1 1 d . . . C6 C 0.20541(18) 0.08771(14) 0.04493(15) 0.0203(4) Uani 1 1 d . . . C7 C 0.29495(18) 0.48067(15) 0.17182(15) 0.0219(4) Uani 1 1 d . . . C8 C 0.22715(17) 0.71406(13) -0.21265(15) 0.0186(4) Uani 1 1 d . . . H8A H 0.1758 0.7365 -0.2889 0.022 Uiso 1 1 calc R . . H8B H 0.3162 0.7149 -0.2108 0.022 Uiso 1 1 calc R . . C9 C 0.2082(2) 0.79341(15) -0.12603(19) 0.0293(5) Uani 1 1 d . . . H9A H 0.1260 0.7792 -0.1142 0.035 Uiso 1 1 calc R . . H9B H 0.2058 0.8671 -0.1565 0.035 Uiso 1 1 calc R . . C10 C 0.3123(3) 0.78766(16) -0.01035(18) 0.0442(7) Uani 1 1 d . . . H10A H 0.2811 0.8224 0.0475 0.053 Uiso 1 1 calc R . . H10B H 0.3295 0.7114 0.0111 0.053 Uiso 1 1 calc R . . C11 C 0.4331(2) 0.84131(18) -0.01102(18) 0.0379(5) Uani 1 1 d . . . H11A H 0.4640 0.8083 -0.0690 0.057 Uiso 1 1 calc R . . H11B H 0.4958 0.8325 0.0628 0.057 Uiso 1 1 calc R . . H11C H 0.4181 0.9180 -0.0273 0.057 Uiso 1 1 calc R . . F1 F 0.22759(13) 0.06260(9) -0.05112(9) 0.0348(3) Uani 1 1 d D . . F2 F 0.31235(10) 0.07866(8) 0.12782(9) 0.0257(3) Uani 1 1 d D . . F3 F 0.12520(11) 0.01718(9) 0.06380(11) 0.0338(3) Uani 1 1 d D . . F4 F 0.21336(11) 0.45607(9) 0.22575(10) 0.0295(3) Uani 1 1 d D . . F5 F 0.38560(12) 0.53866(11) 0.24034(12) 0.0456(4) Uani 1 1 d D . . F6 F 0.23590(13) 0.54247(9) 0.08448(10) 0.0376(3) Uani 1 1 d D . . N1 N 0.20249(13) 0.43587(11) -0.14440(11) 0.0138(3) Uani 1 1 d . . . N2 N 0.19160(13) 0.60377(11) -0.19026(11) 0.0152(3) Uani 1 1 d . . . O1 O 0.03634(11) 0.22101(10) -0.06492(10) 0.0208(3) Uani 1 1 d . . . O2 O 0.12123(11) 0.23998(10) 0.14350(10) 0.0181(3) Uani 1 1 d . . . O3 O 0.39737(12) 0.29485(11) 0.22462(10) 0.0262(3) Uani 1 1 d . . . O4 O 0.45650(12) 0.40695(11) 0.08296(11) 0.0263(3) Uani 1 1 d . . . S1 S 0.14137(4) 0.22509(3) 0.03597(3) 0.01320(12) Uani 1 1 d . . . S2 S 0.36220(4) 0.36018(3) 0.12566(3) 0.01632(12) 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 C1 0.0135(8) 0.0191(8) 0.0091(7) -0.0002(6) 0.0029(6) -0.0007(7) C2 0.0112(8) 0.0203(9) 0.0220(9) 0.0023(7) 0.0026(7) 0.0002(7) C3 0.0123(8) 0.0195(9) 0.0208(9) 0.0014(7) 0.0025(7) -0.0026(7) C4 0.0172(8) 0.0135(8) 0.0132(8) -0.0004(6) 0.0045(7) 0.0023(7) C5 0.0141(8) 0.0142(8) 0.0114(8) -0.0014(6) 0.0024(6) -0.0005(6) C6 0.0262(10) 0.0168(9) 0.0174(9) 0.0008(7) 0.0060(7) 0.0008(7) C7 0.0257(10) 0.0229(9) 0.0192(9) -0.0084(7) 0.0099(8) -0.0088(8) C8 0.0168(9) 0.0181(9) 0.0190(9) 0.0076(7) 0.0024(7) -0.0024(7) C9 0.0309(11) 0.0144(9) 0.0512(13) 0.0022(8) 0.0254(10) 0.0000(8) C10 0.102(2) 0.0163(9) 0.0234(11) 0.0014(8) 0.0326(13) 0.0014(11) C11 0.0462(14) 0.0293(11) 0.0257(11) -0.0042(9) -0.0078(9) 0.0074(10) F1 0.0618(8) 0.0222(6) 0.0233(6) -0.0022(5) 0.0173(6) 0.0123(6) F2 0.0244(6) 0.0239(6) 0.0264(6) 0.0070(4) 0.0040(5) 0.0070(4) F3 0.0357(7) 0.0181(6) 0.0448(7) 0.0060(5) 0.0079(5) -0.0073(5) F4 0.0356(7) 0.0297(6) 0.0325(6) -0.0101(5) 0.0242(5) -0.0070(5) F5 0.0389(7) 0.0499(8) 0.0504(8) -0.0367(7) 0.0171(6) -0.0245(6) F6 0.0667(9) 0.0211(6) 0.0294(6) 0.0001(5) 0.0210(6) 0.0091(6) N1 0.0142(7) 0.0151(7) 0.0113(7) -0.0005(5) 0.0027(5) 0.0003(6) N2 0.0152(7) 0.0160(7) 0.0133(7) 0.0019(6) 0.0028(6) -0.0010(6) O1 0.0175(6) 0.0219(7) 0.0184(6) -0.0004(5) -0.0016(5) -0.0037(5) O2 0.0174(6) 0.0218(6) 0.0167(6) -0.0005(5) 0.0075(5) -0.0010(5) O3 0.0240(7) 0.0346(8) 0.0138(6) -0.0002(5) -0.0034(5) -0.0010(6) O4 0.0172(7) 0.0355(8) 0.0277(7) -0.0087(6) 0.0094(6) -0.0092(6) S1 0.0131(2) 0.0137(2) 0.0117(2) -0.00059(15) 0.00197(16) -0.00062(15) S2 0.0124(2) 0.0220(2) 0.0134(2) -0.00379(16) 0.00210(16) -0.00298(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N2 1.329(2) . ? C1 N1 1.329(2) . ? C1 H1 0.9500 . ? C2 C3 1.349(3) . ? C2 N2 1.382(2) . ? C2 H2 0.9500 . ? C3 N1 1.378(2) . ? C3 H3 0.9500 . ? C4 N1 1.484(2) . ? C4 C5 1.503(2) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 S1 1.6759(17) . ? C5 S2 1.6812(16) . ? C6 F3 1.326(2) . ? C6 F2 1.328(2) . ? C6 F1 1.331(2) . ? C6 S1 1.8446(18) . ? C7 F4 1.323(2) . ? C7 F5 1.325(2) . ? C7 F6 1.334(2) . ? C7 S2 1.8461(19) . ? C8 N2 1.479(2) . ? C8 C9 1.524(3) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.557(3) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.511(4) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? O1 S1 1.4392(12) . ? O2 S1 1.4359(12) . ? O3 S2 1.4292(13) . ? O4 S2 1.4403(13) . ? 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 N2 C1 N1 108.79(14) . . ? N2 C1 H1 125.6 . . ? N1 C1 H1 125.6 . . ? C3 C2 N2 106.96(15) . . ? C3 C2 H2 126.5 . . ? N2 C2 H2 126.5 . . ? C2 C3 N1 107.22(15) . . ? C2 C3 H3 126.4 . . ? N1 C3 H3 126.4 . . ? N1 C4 C5 112.88(13) . . ? N1 C4 H4A 109.0 . . ? C5 C4 H4A 109.0 . . ? N1 C4 H4B 109.0 . . ? C5 C4 H4B 109.0 . . ? H4A C4 H4B 107.8 . . ? C4 C5 S1 120.10(12) . . ? C4 C5 S2 119.11(12) . . ? S1 C5 S2 120.74(10) . . ? F3 C6 F2 107.76(14) . . ? F3 C6 F1 108.89(15) . . ? F2 C6 F1 108.07(15) . . ? F3 C6 S1 110.69(13) . . ? F2 C6 S1 111.59(12) . . ? F1 C6 S1 109.75(12) . . ? F4 C7 F5 108.09(14) . . ? F4 C7 F6 107.46(16) . . ? F5 C7 F6 107.79(16) . . ? F4 C7 S2 112.27(12) . . ? F5 C7 S2 109.80(13) . . ? F6 C7 S2 111.28(12) . . ? N2 C8 C9 111.42(14) . . ? N2 C8 H8A 109.3 . . ? C9 C8 H8A 109.3 . . ? N2 C8 H8B 109.3 . . ? C9 C8 H8B 109.3 . . ? H8A C8 H8B 108.0 . . ? C8 C9 C10 113.59(16) . . ? C8 C9 H9A 108.8 . . ? C10 C9 H9A 108.8 . . ? C8 C9 H9B 108.8 . . ? C10 C9 H9B 108.8 . . ? H9A C9 H9B 107.7 . . ? C11 C10 C9 113.29(17) . . ? C11 C10 H10A 108.9 . . ? C9 C10 H10A 108.9 . . ? C11 C10 H10B 108.9 . . ? C9 C10 H10B 108.9 . . ? H10A C10 H10B 107.7 . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C1 N1 C3 108.51(14) . . ? C1 N1 C4 125.05(14) . . ? C3 N1 C4 126.31(14) . . ? C1 N2 C2 108.51(14) . . ? C1 N2 C8 126.37(14) . . ? C2 N2 C8 125.12(14) . . ? O2 S1 O1 120.16(7) . . ? O2 S1 C5 113.09(8) . . ? O1 S1 C5 109.49(8) . . ? O2 S1 C6 103.34(8) . . ? O1 S1 C6 102.71(8) . . ? C5 S1 C6 106.40(8) . . ? O3 S2 O4 120.46(8) . . ? O3 S2 C5 114.93(8) . . ? O4 S2 C5 107.45(8) . . ? O3 S2 C7 103.04(8) . . ? O4 S2 C7 101.51(8) . . ? C5 S2 C7 107.79(8) . . ? 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 N2 C2 C3 N1 -0.27(19) . . . . ? N1 C4 C5 S1 102.07(15) . . . . ? N1 C4 C5 S2 -80.60(16) . . . . ? N2 C8 C9 C10 76.8(2) . . . . ? C8 C9 C10 C11 76.8(2) . . . . ? N2 C1 N1 C3 -0.51(18) . . . . ? N2 C1 N1 C4 -176.65(14) . . . . ? C2 C3 N1 C1 0.49(19) . . . . ? C2 C3 N1 C4 176.56(15) . . . . ? C5 C4 N1 C1 106.37(18) . . . . ? C5 C4 N1 C3 -69.1(2) . . . . ? N1 C1 N2 C2 0.34(18) . . . . ? N1 C1 N2 C8 179.66(15) . . . . ? C3 C2 N2 C1 -0.03(19) . . . . ? C3 C2 N2 C8 -179.37(15) . . . . ? C9 C8 N2 C1 -111.23(19) . . . . ? C9 C8 N2 C2 68.0(2) . . . . ? C4 C5 S1 O2 -159.63(12) . . . . ? S2 C5 S1 O2 23.08(13) . . . . ? C4 C5 S1 O1 -22.72(15) . . . . ? S2 C5 S1 O1 159.99(10) . . . . ? C4 C5 S1 C6 87.60(14) . . . . ? S2 C5 S1 C6 -89.68(12) . . . . ? F3 C6 S1 O2 59.17(14) . . . . ? F2 C6 S1 O2 -60.85(14) . . . . ? F1 C6 S1 O2 179.39(12) . . . . ? F3 C6 S1 O1 -66.48(14) . . . . ? F2 C6 S1 O1 173.50(12) . . . . ? F1 C6 S1 O1 53.74(14) . . . . ? F3 C6 S1 C5 178.50(12) . . . . ? F2 C6 S1 C5 58.49(14) . . . . ? F1 C6 S1 C5 -61.28(14) . . . . ? C4 C5 S2 O3 -146.25(12) . . . . ? S1 C5 S2 O3 31.06(14) . . . . ? C4 C5 S2 O4 -9.18(15) . . . . ? S1 C5 S2 O4 168.13(10) . . . . ? C4 C5 S2 C7 99.51(14) . . . . ? S1 C5 S2 C7 -83.18(12) . . . . ? F4 C7 S2 O3 -48.04(14) . . . . ? F5 C7 S2 O3 72.22(14) . . . . ? F6 C7 S2 O3 -168.53(13) . . . . ? F4 C7 S2 O4 -173.36(12) . . . . ? F5 C7 S2 O4 -53.10(15) . . . . ? F6 C7 S2 O4 66.15(14) . . . . ? F4 C7 S2 C5 73.88(14) . . . . ? F5 C7 S2 C5 -165.86(13) . . . . ? F6 C7 S2 C5 -46.61(15) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.506 _refine_diff_density_min -0.339 _refine_diff_density_rms 0.050 _database_code_depnum_ccdc_archive 'CCDC 948832'