# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_address ; University of Innsbruck Faculty of Chemistry and Pharmacy Innrain 52a 6020 Innsbruck Austria ; _publ_contact_author_email gerhard.laus@uibk.ac.at _publ_contact_author_name 'Laus, Gerhard' _publ_section_title ; The 1:1 and 1:2 salts of 1,4-diazabicyclo[2.2.2]octane (DABCO) and bis(trifluoromethylsulfonyl)amine ; loop_ _publ_author_name 'Gerhard Laus' 'Michael Hummel' 'Daniel M. Tobbens' 'Thomas Gelbrich' 'Volker Kahlenberg' 'Klaus Wurst' 'Ulrich J. Griesser' 'Herwig Schottenberger' data_1 _database_code_depnum_ccdc_archive 'CCDC 797203' #============================================================================= loop_ _publ_manuscript_incl_extra_item _publ_manuscript_incl_extra_info _publ_manuscript_incl_extra_defn # Name Explanation Standard? # ------ ----------- --------- '_pd_proc_ls_prof_cR_factor' 'Prof. R-factor CORRECTED for background' no '_pd_proc_ls_prof_cwR_factor' 'wProf.R-factor CORRECTED for background' no '_pd_proc_ls_prof_cwR_expected' 'wProf.Expected CORRECTED for background' no '_pd_proc_ls_prof_chi2' 'Chi-square for all considered points' no '_pd_proc_ls_prof_echi2' 'Chi-2 for points with Bragg contribution' no #============================================================================= _audit_creation_date 2009-09-10T13:10:12-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C6 H13 N2, C2 F6 N O4 S2' _chemical_formula_sum 'C8 H13 F6 N3 O4 S2' _chemical_formula_weight 393.33 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/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 12.5385(3) _cell_length_b 16.8869(3) _cell_length_c 15.9960(4) _cell_angle_alpha 90 _cell_angle_beta 112.8440(10) _cell_angle_gamma 90 _cell_volume 3121.28(12) _cell_formula_units_Z 8 _cell_measurement_temperature 233(2) _cell_measurement_reflns_used 22009 _cell_measurement_theta_min 1 _cell_measurement_theta_max 25 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.15 _exptl_crystal_density_diffrn 1.674 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1600 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.426 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 233(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'phi- and omega-scans' _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0.0249 _diffrn_reflns_av_unetI/netI 0.0247 _diffrn_reflns_number 17766 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.21 _diffrn_reflns_theta_max 25.05 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.995 _reflns_number_total 5592 _reflns_number_gt 4812 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection COLLECT _computing_cell_refinement 'SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO and SCALEPACK' _computing_structure_solution 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0526P)^2^+1.9204P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.0049(9) _refine_ls_number_reflns 5592 _refine_ls_number_parameters 430 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0521 _refine_ls_R_factor_gt 0.043 _refine_ls_wR_factor_ref 0.1139 _refine_ls_wR_factor_gt 0.1088 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.319 _refine_diff_density_min -0.349 _refine_diff_density_rms 0.043 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.21404(6) 0.48273(4) 0.67817(4) 0.0518(2) Uani 1 1 d . . . S2 S 0.14786(6) 0.32451(4) 0.66978(5) 0.0517(2) Uani 1 1 d . . . S3 S 0.22150(6) 0.73913(4) 0.18321(5) 0.0529(2) Uani 1 1 d . . . S4 S 0.28181(6) 0.58136(4) 0.17860(5) 0.0503(2) Uani 1 1 d . . . N1 N 0.20780(19) 0.40100(13) 0.72331(14) 0.0487(5) Uani 1 1 d . . . N2 N 0.27274(19) 0.65837(13) 0.23007(14) 0.0480(5) Uani 1 1 d . . . N3 N 0.06718(18) 0.93454(11) 0.50423(13) 0.0403(5) Uani 1 1 d D . . H3N H 0.026(4) 0.976(2) 0.508(4) 0.048 Uiso 0.5 1 d PD A 1 N4 N 0.18935(16) 0.81595(11) 0.50765(13) 0.0347(4) Uani 1 1 d D . . H4N H 0.233(4) 0.7736(18) 0.514(3) 0.042 Uiso 0.5 1 d PD B 2 N5 N 0.31678(16) 0.68450(11) 0.50544(13) 0.0340(4) Uani 1 1 d D . . H5N H 0.272(3) 0.7254(17) 0.504(3) 0.029(12) Uiso 0.5 1 d PD C 1 N6 N 0.43607(15) 0.56567(10) 0.50196(13) 0.0332(4) Uani 1 1 d D . . H6N H 0.477(4) 0.5236(19) 0.499(4) 0.04 Uiso 0.5 1 d PD D 2 O1 O 0.2000(2) 0.47998(15) 0.58608(14) 0.0782(7) Uani 1 1 d . . . O2 O 0.30906(18) 0.52594(13) 0.74038(15) 0.0704(6) Uani 1 1 d . . . O3 O 0.05500(19) 0.33648(14) 0.58514(15) 0.0737(6) Uani 1 1 d . . . O4 O 0.1313(2) 0.27115(13) 0.73265(15) 0.0743(6) Uani 1 1 d . . . O5 O 0.1831(2) 0.78243(15) 0.24252(18) 0.0832(7) Uani 1 1 d . . . O6 O 0.1488(2) 0.73495(15) 0.09015(15) 0.0822(7) Uani 1 1 d . . . O7 O 0.3603(2) 0.52905(13) 0.24270(17) 0.0791(7) Uani 1 1 d . . . O8 O 0.2920(2) 0.59262(14) 0.09435(15) 0.0744(6) Uani 1 1 d . . . C1 C 0.0870(3) 0.5364(2) 0.6782(3) 0.0758(9) Uani 1 1 d . . . C2 C 0.2604(3) 0.2765(3) 0.6423(3) 0.0816(10) Uani 1 1 d . . . C3 C 0.3490(3) 0.7940(2) 0.1859(3) 0.0744(9) Uani 1 1 d . . . C4 C 0.1428(3) 0.5326(2) 0.1512(3) 0.0770(10) Uani 1 1 d . . . C5 C 0.0397(2) 0.90691(15) 0.41058(17) 0.0453(6) Uani 1 1 d . . . H5A H 0.0529 0.9498 0.3744 0.054 Uiso 1 1 calc . . . H5B H -0.0419 0.8914 0.3826 0.054 Uiso 1 1 calc . . . C6 C 0.1165(2) 0.83627(15) 0.41255(16) 0.0417(6) Uani 1 1 d . . . H6A H 0.0683 0.7908 0.3826 0.05 Uiso 1 1 calc . . . H6B H 0.1658 0.8493 0.3797 0.05 Uiso 1 1 calc . . . C7 C 0.1912(2) 0.95648(14) 0.54780(17) 0.0443(6) Uani 1 1 d . . . H7A H 0.2085 0.9763 0.6092 0.053 Uiso 1 1 calc . . . H7B H 0.2088 0.9985 0.5128 0.053 Uiso 1 1 calc . . . C8 C 0.2654(2) 0.88353(14) 0.55182(17) 0.0420(6) Uani 1 1 d . . . H8A H 0.3175 0.8946 0.5208 0.05 Uiso 1 1 calc . . . H8B H 0.3126 0.8704 0.6152 0.05 Uiso 1 1 calc . . . C9 C 0.0432(2) 0.87078(15) 0.55857(19) 0.0465(6) Uani 1 1 d . . . H9A H -0.0394 0.8576 0.5327 0.056 Uiso 1 1 calc . . . H9B H 0.0633 0.8889 0.621 0.056 Uiso 1 1 calc . . . C10 C 0.1143(2) 0.79787(13) 0.55809(16) 0.0397(5) Uani 1 1 d . . . H10A H 0.1624 0.7825 0.6205 0.048 Uiso 1 1 calc . . . H10B H 0.0627 0.7536 0.529 0.048 Uiso 1 1 calc . . . C11 C 0.3842(2) 0.65740(14) 0.59962(16) 0.0416(6) Uani 1 1 d . . . H11A H 0.3314 0.6436 0.6292 0.05 Uiso 1 1 calc . . . H11B H 0.4351 0.7001 0.6344 0.05 Uiso 1 1 calc . . . C12 C 0.4564(2) 0.58520(14) 0.59745(16) 0.0401(5) Uani 1 1 d . . . H12A H 0.5386 0.5964 0.6315 0.048 Uiso 1 1 calc . . . H12B H 0.4348 0.54 0.626 0.048 Uiso 1 1 calc . . . C13 C 0.2393(2) 0.62029(14) 0.45240(18) 0.0419(6) Uani 1 1 d . . . H13A H 0.1952 0.6385 0.3903 0.05 Uiso 1 1 calc . . . H13B H 0.1844 0.6062 0.48 0.05 Uiso 1 1 calc . . . C14 C 0.3115(2) 0.54770(13) 0.45066(16) 0.0375(5) Uani 1 1 d . . . H14A H 0.2886 0.5024 0.4782 0.045 Uiso 1 1 calc . . . H14B H 0.2981 0.5341 0.3878 0.045 Uiso 1 1 calc . . . C15 C 0.3970(2) 0.70628(13) 0.46124(17) 0.0386(5) Uani 1 1 d . . . H15A H 0.4478 0.7494 0.4949 0.046 Uiso 1 1 calc . . . H15B H 0.3528 0.7247 0.3993 0.046 Uiso 1 1 calc . . . C16 C 0.4699(2) 0.63399(14) 0.45913(17) 0.0383(5) Uani 1 1 d . . . H16A H 0.4573 0.6211 0.3963 0.046 Uiso 1 1 calc . . . H16B H 0.5523 0.6457 0.4921 0.046 Uiso 1 1 calc . . . F1 F 0.0856(3) 0.60792(14) 0.6427(2) 0.1212(9) Uani 1 1 d . . . F2 F 0.0928(2) 0.54552(16) 0.76175(18) 0.1036(7) Uani 1 1 d . . . F3 F -0.00978(18) 0.49997(16) 0.63119(18) 0.1079(8) Uani 1 1 d . . . F4 F 0.2923(3) 0.31813(19) 0.5889(2) 0.1398(12) Uani 1 1 d . . . F5 F 0.3513(2) 0.2626(2) 0.7167(2) 0.1485(13) Uani 1 1 d . . . F6 F 0.2241(3) 0.20785(16) 0.6039(2) 0.1330(11) Uani 1 1 d . . . F7 F 0.3143(3) 0.86411(14) 0.1481(2) 0.1223(9) Uani 1 1 d . . . F8 F 0.4216(2) 0.80475(15) 0.26986(18) 0.1050(8) Uani 1 1 d . . . F9 F 0.4026(2) 0.75702(14) 0.14171(18) 0.1012(8) Uani 1 1 d . . . F10 F 0.0574(2) 0.5729(2) 0.0961(2) 0.1381(11) Uani 1 1 d . . . F11 F 0.1235(2) 0.5206(2) 0.22530(19) 0.1319(11) Uani 1 1 d . . . F12 F 0.1430(3) 0.46224(16) 0.1151(2) 0.1249(10) 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 0.0514(4) 0.0600(4) 0.0421(4) 0.0051(3) 0.0163(3) -0.0172(3) S2 0.0494(4) 0.0573(4) 0.0427(4) -0.0005(3) 0.0118(3) -0.0142(3) S3 0.0506(4) 0.0576(4) 0.0495(4) 0.0048(3) 0.0182(3) 0.0200(3) S4 0.0539(4) 0.0534(4) 0.0459(4) -0.0014(3) 0.0219(3) 0.0108(3) N1 0.0515(13) 0.0562(13) 0.0339(11) 0.0003(10) 0.0117(10) -0.0161(10) N2 0.0553(13) 0.0526(13) 0.0349(11) 0.0011(9) 0.0163(10) 0.0143(10) N3 0.0486(12) 0.0323(10) 0.0420(11) 0.0056(8) 0.0197(9) 0.0190(9) N4 0.0345(10) 0.0309(10) 0.0380(10) -0.0002(8) 0.0133(8) 0.0107(8) N5 0.0341(10) 0.0297(10) 0.0385(10) 0.0001(8) 0.0146(8) 0.0109(8) N6 0.0324(10) 0.0287(10) 0.0394(10) -0.0025(8) 0.0150(8) 0.0078(8) O1 0.1015(18) 0.0896(16) 0.0492(12) 0.0113(11) 0.0354(12) -0.0236(14) O2 0.0615(12) 0.0741(14) 0.0668(14) -0.0042(11) 0.0155(11) -0.0333(11) O3 0.0624(13) 0.0773(15) 0.0554(13) -0.0033(11) -0.0055(10) -0.0194(11) O4 0.0925(17) 0.0628(13) 0.0698(14) 0.0083(11) 0.0338(13) -0.0254(12) O5 0.0930(17) 0.0778(15) 0.0973(18) -0.0084(13) 0.0573(15) 0.0306(13) O6 0.0765(15) 0.0852(17) 0.0586(13) 0.0138(12) -0.0025(11) 0.0246(13) O7 0.0795(15) 0.0631(14) 0.0810(16) 0.0115(12) 0.0160(13) 0.0306(12) O8 0.1041(18) 0.0751(14) 0.0643(14) -0.0104(11) 0.0549(14) 0.0038(13) C1 0.069(2) 0.068(2) 0.081(2) 0.0054(18) 0.0195(19) -0.0002(17) C2 0.076(2) 0.093(3) 0.078(2) -0.017(2) 0.032(2) -0.004(2) C3 0.087(2) 0.062(2) 0.080(2) 0.0017(18) 0.038(2) 0.0031(18) C4 0.076(2) 0.084(3) 0.071(2) -0.0110(19) 0.028(2) -0.014(2) C5 0.0473(14) 0.0446(14) 0.0368(13) 0.0044(10) 0.0083(11) 0.0132(11) C6 0.0450(13) 0.0455(14) 0.0350(13) -0.0033(10) 0.0160(11) 0.0081(11) C7 0.0563(15) 0.0332(12) 0.0408(14) 0.0003(10) 0.0161(12) 0.0011(11) C8 0.0369(13) 0.0422(13) 0.0456(14) -0.0019(11) 0.0145(11) 0.0009(10) C9 0.0473(15) 0.0466(14) 0.0563(16) 0.0076(12) 0.0317(13) 0.0118(11) C10 0.0451(13) 0.0326(12) 0.0427(13) 0.0045(10) 0.0187(11) 0.0050(10) C11 0.0522(14) 0.0391(13) 0.0347(12) -0.0003(10) 0.0181(11) 0.0140(11) C12 0.0440(13) 0.0382(13) 0.0350(12) 0.0020(10) 0.0118(10) 0.0135(10) C13 0.0289(11) 0.0402(13) 0.0526(15) -0.0025(11) 0.0115(11) 0.0040(10) C14 0.0357(12) 0.0325(12) 0.0431(13) -0.0068(10) 0.0139(10) 0.0005(9) C15 0.0399(13) 0.0318(12) 0.0455(13) 0.0051(10) 0.0181(11) 0.0048(10) C16 0.0374(13) 0.0374(12) 0.0446(13) -0.0034(10) 0.0209(11) 0.0006(10) F1 0.136(2) 0.0694(14) 0.149(2) 0.0352(15) 0.0456(19) 0.0191(14) F2 0.1043(17) 0.1163(19) 0.1033(18) -0.0138(14) 0.0545(15) 0.0109(14) F3 0.0540(12) 0.1116(18) 0.132(2) -0.0081(15) 0.0078(12) 0.0023(12) F4 0.173(3) 0.136(2) 0.177(3) -0.015(2) 0.141(3) -0.004(2) F5 0.0859(18) 0.206(3) 0.130(2) -0.034(2) 0.0154(17) 0.058(2) F6 0.158(3) 0.0962(18) 0.154(3) -0.0548(18) 0.070(2) -0.0062(18) F7 0.156(2) 0.0654(14) 0.154(2) 0.0311(15) 0.069(2) 0.0030(15) F8 0.0856(15) 0.1094(18) 0.1070(19) -0.0226(14) 0.0231(14) -0.0216(13) F9 0.1060(17) 0.0992(16) 0.133(2) -0.0084(14) 0.0840(16) -0.0099(13) F10 0.0611(14) 0.142(2) 0.162(3) 0.007(2) -0.0100(15) -0.0136(15) F11 0.129(2) 0.177(3) 0.117(2) -0.0262(19) 0.0773(19) -0.072(2) F12 0.143(2) 0.0921(18) 0.139(2) -0.0489(16) 0.0542(19) -0.0427(16) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O1 1.415(2) . ? S1 O2 1.422(2) . ? S1 N1 1.574(2) . ? S1 C1 1.833(4) . ? S2 O3 1.416(2) . ? S2 O4 1.424(2) . ? S2 N1 1.571(2) . ? S2 C2 1.824(4) . ? S3 O6 1.413(2) . ? S3 O5 1.421(2) . ? S3 N2 1.569(2) . ? S3 C3 1.834(4) . ? S4 O8 1.415(2) . ? S4 O7 1.420(2) . ? S4 N2 1.567(2) . ? S4 C4 1.820(4) . ? N3 C5 1.476(3) . ? N3 C7 1.483(3) . ? N3 C9 1.486(3) . ? N3 H3N 0.890(10) . ? N4 C6 1.479(3) . ? N4 C8 1.479(3) . ? N4 C10 1.489(3) . ? N4 H4N 0.883(10) . ? N5 C13 1.483(3) . ? N5 C15 1.483(3) . ? N5 C11 1.485(3) . ? N5 H5N 0.884(10) . ? N6 C12 1.485(3) . ? N6 C16 1.485(3) . ? N6 C14 1.486(3) . ? N6 H6N 0.884(10) . ? C1 F3 1.307(4) . ? C1 F2 1.319(4) . ? C1 F1 1.331(4) . ? C2 F4 1.284(5) . ? C2 F6 1.308(5) . ? C2 F5 1.311(5) . ? C3 F9 1.308(4) . ? C3 F8 1.310(4) . ? C3 F7 1.324(4) . ? C4 F10 1.286(5) . ? C4 F11 1.315(4) . ? C4 F12 1.321(4) . ? C5 C6 1.526(3) . ? C5 H5A 0.98 . ? C5 H5B 0.98 . ? C6 H6A 0.98 . ? C6 H6B 0.98 . ? C7 C8 1.530(3) . ? C7 H7A 0.98 . ? C7 H7B 0.98 . ? C8 H8A 0.98 . ? C8 H8B 0.98 . ? C9 C10 1.522(3) . ? C9 H9A 0.98 . ? C9 H9B 0.98 . ? C10 H10A 0.98 . ? C10 H10B 0.98 . ? C11 C12 1.527(3) . ? C11 H11A 0.98 . ? C11 H11B 0.98 . ? C12 H12A 0.98 . ? C12 H12B 0.98 . ? C13 C14 1.530(3) . ? C13 H13A 0.98 . ? C13 H13B 0.98 . ? C14 H14A 0.98 . ? C14 H14B 0.98 . ? C15 C16 1.533(3) . ? C15 H15A 0.98 . ? C15 H15B 0.98 . ? C16 H16A 0.98 . ? C16 H16B 0.98 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 S1 O2 118.53(14) . . ? O1 S1 N1 116.14(14) . . ? O2 S1 N1 107.84(13) . . ? O1 S1 C1 105.04(17) . . ? O2 S1 C1 103.77(16) . . ? N1 S1 C1 103.63(15) . . ? O3 S2 O4 118.32(14) . . ? O3 S2 N1 116.46(13) . . ? O4 S2 N1 107.78(13) . . ? O3 S2 C2 105.01(17) . . ? O4 S2 C2 103.13(18) . . ? N1 S2 C2 104.25(16) . . ? O6 S3 O5 118.81(16) . . ? O6 S3 N2 115.90(14) . . ? O5 S3 N2 108.07(14) . . ? O6 S3 C3 104.46(17) . . ? O5 S3 C3 104.01(17) . . ? N2 S3 C3 103.67(15) . . ? O8 S4 O7 118.55(15) . . ? O8 S4 N2 116.15(13) . . ? O7 S4 N2 107.95(13) . . ? O8 S4 C4 105.24(16) . . ? O7 S4 C4 102.89(17) . . ? N2 S4 C4 104.12(16) . . ? S2 N1 S1 124.73(13) . . ? S4 N2 S3 124.77(14) . . ? C5 N3 C7 110.18(19) . . ? C5 N3 C9 110.1(2) . . ? C7 N3 C9 108.65(19) . . ? C5 N3 H3N 114(4) . . ? C7 N3 H3N 107(4) . . ? C9 N3 H3N 106(4) . . ? C6 N4 C8 109.78(18) . . ? C6 N4 C10 109.71(18) . . ? C8 N4 C10 108.96(18) . . ? C6 N4 H4N 114(3) . . ? C8 N4 H4N 108(3) . . ? C10 N4 H4N 106(3) . . ? C13 N5 C15 108.86(18) . . ? C13 N5 C11 110.09(18) . . ? C15 N5 C11 109.63(18) . . ? C13 N5 H5N 107(3) . . ? C15 N5 H5N 109(3) . . ? C11 N5 H5N 112(3) . . ? C12 N6 C16 109.66(17) . . ? C12 N6 C14 109.70(17) . . ? C16 N6 C14 109.34(17) . . ? C12 N6 H6N 111(4) . . ? C16 N6 H6N 109(4) . . ? C14 N6 H6N 108(4) . . ? F3 C1 F2 108.2(3) . . ? F3 C1 F1 109.0(3) . . ? F2 C1 F1 108.2(3) . . ? F3 C1 S1 112.3(3) . . ? F2 C1 S1 110.6(3) . . ? F1 C1 S1 108.5(3) . . ? F4 C2 F6 108.3(4) . . ? F4 C2 F5 108.5(4) . . ? F6 C2 F5 106.8(4) . . ? F4 C2 S2 112.7(3) . . ? F6 C2 S2 110.3(3) . . ? F5 C2 S2 110.0(3) . . ? F9 C3 F8 108.8(3) . . ? F9 C3 F7 109.1(3) . . ? F8 C3 F7 108.6(3) . . ? F9 C3 S3 111.9(3) . . ? F8 C3 S3 110.3(3) . . ? F7 C3 S3 108.2(3) . . ? F10 C4 F11 107.7(4) . . ? F10 C4 F12 108.6(3) . . ? F11 C4 F12 106.6(3) . . ? F10 C4 S4 113.0(3) . . ? F11 C4 S4 110.3(3) . . ? F12 C4 S4 110.4(3) . . ? N3 C5 C6 109.22(19) . . ? N3 C5 H5A 109.8 . . ? C6 C5 H5A 109.8 . . ? N3 C5 H5B 109.8 . . ? C6 C5 H5B 109.8 . . ? H5A C5 H5B 108.3 . . ? N4 C6 C5 109.59(18) . . ? N4 C6 H6A 109.8 . . ? C5 C6 H6A 109.8 . . ? N4 C6 H6B 109.8 . . ? C5 C6 H6B 109.8 . . ? H6A C6 H6B 108.2 . . ? N3 C7 C8 109.14(19) . . ? N3 C7 H7A 109.9 . . ? C8 C7 H7A 109.9 . . ? N3 C7 H7B 109.9 . . ? C8 C7 H7B 109.9 . . ? H7A C7 H7B 108.3 . . ? N4 C8 C7 109.44(19) . . ? N4 C8 H8A 109.8 . . ? C7 C8 H8A 109.8 . . ? N4 C8 H8B 109.8 . . ? C7 C8 H8B 109.8 . . ? H8A C8 H8B 108.2 . . ? N3 C9 C10 109.30(19) . . ? N3 C9 H9A 109.8 . . ? C10 C9 H9A 109.8 . . ? N3 C9 H9B 109.8 . . ? C10 C9 H9B 109.8 . . ? H9A C9 H9B 108.3 . . ? N4 C10 C9 109.38(18) . . ? N4 C10 H10A 109.8 . . ? C9 C10 H10A 109.8 . . ? N4 C10 H10B 109.8 . . ? C9 C10 H10B 109.8 . . ? H10A C10 H10B 108.2 . . ? N5 C11 C12 109.38(18) . . ? N5 C11 H11A 109.8 . . ? C12 C11 H11A 109.8 . . ? N5 C11 H11B 109.8 . . ? C12 C11 H11B 109.8 . . ? H11A C11 H11B 108.2 . . ? N6 C12 C11 109.53(18) . . ? N6 C12 H12A 109.8 . . ? C11 C12 H12A 109.8 . . ? N6 C12 H12B 109.8 . . ? C11 C12 H12B 109.8 . . ? H12A C12 H12B 108.2 . . ? N5 C13 C14 109.62(18) . . ? N5 C13 H13A 109.7 . . ? C14 C13 H13A 109.7 . . ? N5 C13 H13B 109.7 . . ? C14 C13 H13B 109.7 . . ? H13A C13 H13B 108.2 . . ? N6 C14 C13 109.17(18) . . ? N6 C14 H14A 109.8 . . ? C13 C14 H14A 109.8 . . ? N6 C14 H14B 109.8 . . ? C13 C14 H14B 109.8 . . ? H14A C14 H14B 108.3 . . ? N5 C15 C16 109.49(18) . . ? N5 C15 H15A 109.8 . . ? C16 C15 H15A 109.8 . . ? N5 C15 H15B 109.8 . . ? C16 C15 H15B 109.8 . . ? H15A C15 H15B 108.2 . . ? N6 C16 C15 109.18(18) . . ? N6 C16 H16A 109.8 . . ? C15 C16 H16A 109.8 . . ? N6 C16 H16B 109.8 . . ? C15 C16 H16B 109.8 . . ? H16A C16 H16B 108.3 . . ? 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 C1 S1 N1 S2 92.9(2) . . . . ? S1 N1 S2 C2 87.0(2) . . . . ? C3 S3 N2 S4 -94.1(2) . . . . ? S3 N2 S4 C4 -87.3(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N3 H3N N3 0.890(10) 1.869(14) 2.751(3) 170(5) 3_576 N4 H4N N5 0.883(10) 1.869(13) 2.743(2) 170(5) . N5 H5N N4 0.884(10) 1.862(11) 2.743(2) 175(4) . N6 H6N N6 0.884(10) 1.868(11) 2.752(3) 178(5) 3_666 # Attachment 'MH640-333K.cif' data_DABCO-triflimide-1-MH460 _database_code_depnum_ccdc_archive 'CCDC 797204' #TrackingRef 'MH640-333K.cif' #============================================================================= # 5. CHEMICAL DATA _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_iupac ? _chemical_formula_sum ? _chemical_formula_weight ? _chemical_melting_point ? _chemical_compound_source ? # for minerals and # natural products loop_ _atom_type_symbol _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source s 6.90530 1.46790 5.20340 22.21510 1.43790 0.25360 1.58630 56.17200 0.86690 0.31900 0.55700 International_Tables_for_Crystallography_Vol.C(1991)_Tables_6.1.1.4_and_6.1.1.5 o 3.04850 13.27710 2.28680 5.70110 1.54630 0.32390 0.86700 32.90890 0.25080 0.04700 0.03200 International_Tables_for_Crystallography_Vol.C(1991)_Tables_6.1.1.4_and_6.1.1.5 n 12.21260 0.00570 3.13220 9.89330 2.01250 28.99750 1.16630 0.58260 -11.52900 0.02900 0.01800 International_Tables_for_Crystallography_Vol.C(1991)_Tables_6.1.1.4_and_6.1.1.5 f 3.53920 10.28250 2.64120 4.29440 1.51700 0.26150 1.02430 26.14760 0.27760 0.06900 0.05300 International_Tables_for_Crystallography_Vol.C(1991)_Tables_6.1.1.4_and_6.1.1.5 c 2.31000 20.84390 1.02000 10.20750 1.58860 0.56870 0.86500 51.65120 0.21560 0.01700 0.00900 International_Tables_for_Crystallography_Vol.C(1991)_Tables_6.1.1.4_and_6.1.1.5 #============================================================================= # 6. POWDER SPECIMEN AND CRYSTAL DATA _symmetry_cell_setting Hexagonal _symmetry_space_group_name_H-M 'P 63 C M' _symmetry_space_group_name_Hall 'P 6c -2' loop_ _symmetry_equiv_pos_as_xyz #<--must include 'x,y,z' x,y,z x-y,x,z+1/2 -y,x-y,z -x,-y,z+1/2 -x+y,-x,z y,-x+y,z+1/2 -y,-x,z+1/2 -x,-x+y,z -x+y,y,z+1/2 y,x,z x,x-y,z+1/2 x-y,-y,z _cell_length_a 16.27841 _cell_length_b 16.27841 _cell_length_c 10.57230380(11) _cell_angle_alpha 90.00000 _cell_angle_beta 90.00000 _cell_angle_gamma 120.00000 _cell_volume 2426.19(2) _cell_formula_units_Z ? _cell_measurement_temperature ? _cell_special_details ; ? ; # The next three fields give the specimen dimensions in mm. The equatorial # plane contains the incident and diffracted beam. _pd_spec_size_axial ? # perpendicular to # equatorial plane _pd_spec_size_equat ? # parallel to # scattering vector # in transmission _pd_spec_size_thick ? # parallel to # scattering vector # in reflection # The next five fields are character fields that describe the specimen. _pd_spec_mounting # This field should be # used to give details of the # container. ; ? ; _pd_spec_mount_mode ? # options are 'reflection' # or 'transmission' _pd_spec_shape ? # options are 'cylinder' # 'flat_sheet' or 'irregular' _pd_char_particle_morphology ? _pd_char_colour ? # use ICDD colour descriptions # The following three fields describe the preparation of the specimen. # The cooling rate is in K/min. The pressure at which the sample was # prepared is in kPa. The temperature of preparation is in K. _pd_prep_cool_rate ? _pd_prep_pressure ? _pd_prep_temperature ? # The next four fields are normally only needed for transmission experiments. _exptl_absorpt_coefficient_mu ? _exptl_absorpt_correction_type ? _exptl_absorpt_process_details ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? #============================================================================= # 7. EXPERIMENTAL DATA _exptl_special_details ; ? ; # The following item is used to identify the equipment used to record # the powder pattern when the diffractogram was measured at a laboratory # other than the authors' home institution, e.g. when neutron or synchrotron # radiation is used. _pd_instr_location ; ? ; _pd_calibration_special_details # description of the method used # to calibrate the instrument ; ? ; _diffrn_ambient_temperature ? _diffrn_source ? # Put here: 'rotating-anode X-ray tube' _diffrn_radiation_type X-ray _diffrn_source_target ? # Put here the chemical symbol of the anode _diffrn_radiation_monochromator ? _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? # Not in version 2.0.1 _diffrn_detector ? _diffrn_detector_type ? # make or model of detector _pd_meas_scan_method ? # options are 'step', 'cont', # 'tof', 'fixed' or # 'disp' (= dispersive) _pd_meas_special_details ; ? ; # The following four items give details of the measured (not processed) # powder pattern. Angles are in degrees. _pd_meas_number_of_points 7545 _pd_meas_2theta_range_min 3.05400 _pd_meas_2theta_range_max 70.95000 _pd_meas_2theta_range_inc 0.009001 #============================================================================= # 8. REFINEMENT DATA _refine_special_details ; ? ; # Use the next field to give any special details about the fitting of the # powder pattern. _pd_proc_ls_special_details ; ? ; # The next three items are given as text. _pd_proc_ls_profile_function ? _pd_proc_ls_background_function ? _pd_proc_ls_pref_orient_corr ; ? ; # The following profile R-factors are NOT CORRECTED for background # The sum is extended to all non-excluded points. # These are the current CIF standard _pd_proc_ls_prof_R_factor 4.6263 _pd_proc_ls_prof_wR_factor 6.8005 _pd_proc_ls_prof_wR_expected 4.6273 # The following profile R-factors are CORRECTED for background # The sum is extended to all non-excluded points. # These items are not in the current CIF standard, but are defined above _pd_proc_ls_prof_cR_factor 16.4796 _pd_proc_ls_prof_cwR_factor 13.7520 _pd_proc_ls_prof_cwR_expected 9.3573 # The following items are not in the CIF standard, but are defined above _pd_proc_ls_prof_chi2 2.1599 _pd_proc_ls_prof_echi2 2.4048 # Items related to LS refinement _refine_ls_R_I_factor 5.0572 _refine_ls_number_reflns 234 _refine_ls_number_parameters 81 _refine_ls_number_restraints 48 # The following four items apply to angular dispersive measurements. # 2theta minimum, maximum and increment (in degrees) are for the # intensities used in the refinement. _pd_proc_2theta_range_min 3.0540 _pd_proc_2theta_range_max 70.9500 _pd_proc_2theta_range_inc 0.009001 _pd_proc_wavelength 1.540593 _pd_block_diffractogram_id ? # The id used for the block containing # the powder pattern profile (section 11) # Give appropriate details in the next two text fields. _pd_proc_info_excluded_regions ? _pd_proc_info_data_reduction ? # The following items are used to identify the programs used. _computing_data_collection ? _computing_structure_solution ? _computing_structure_refinement FULLPROF _computing_molecular_graphics ? _computing_publication_material ? #============================================================================= # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type # Not in version 2.0.1 _atom_site_type_symbol S2 0.2941(5) 0.00000 0.9788(8) 0.422(9) 1.00000 Uani S S9 0.3746(6) 0.00000 0.7426(8) 0.422(9) 1.00000 Uani S O7 0.2121(8) 0.00000 1.014(3) 0.422(9) 1.00000 Uani O C10 0.3244(3) 0.00000 0.5951(5) 0.422(9) 1.00000 Uani N F5 0.4258(4) 0.00000 1.116(3) 0.422(9) 1.00000 Uani F F12 0.2468(4) 0.00000 0.6227(11) 0.422(9) 1.00000 Uani F N1 0.332(2) 0.0418(18) 0.8422(15) 0.422(9) 0.50000 Uani N O8 0.2364(19) -0.1016(8) 0.990(4) 0.422(9) 0.50000 Uani O O15 0.3778(9) -0.0769(8) 0.794(3) 0.422(9) 1.00000 Uani O C3 0.3862(3) 0.0534(3) 1.1062(6) 0.422(9) 0.50000 Uani N F4 0.4649(18) 0.1372(14) 1.115(3) 0.422(9) 0.50000 Uani F F6 0.3352(12) 0.058(2) 1.1989(16) 0.422(9) 0.50000 Uani F F11 0.2717(15) -0.0834(11) 0.637(3) 0.422(9) 0.50000 Uani F F13 0.3343(16) -0.040(2) 0.4934(18) 0.422(9) 0.50000 Uani F N1a 0.00000 0.00000 0.4197(4) 0.022(4) 1.00000 Uiso N N2a 0.00000 0.00000 0.1833(4) 0.022(4) 1.00000 Uiso N C3a 0.00000 0.0865(3) 0.3822(4) 0.022(4) 1.00000 Uiso C C4a 0.00000 0.0854(3) 0.2377(4) 0.022(4) 1.00000 Uiso C N1b 0.33333 0.66667 0.2664(7) 0.140(5) 1.00000 Uiso N N2b 0.33333 0.66667 0.4980(7) 0.140(5) 1.00000 Uiso N C3b 0.3238(12) 0.7482(8) 0.3048(5) 0.140(5) 1.00000 Uiso C C4b 0.3437(13) 0.7566(6) 0.4455(5) 0.140(5) 1.00000 Uiso C loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 _atom_site_aniso_type_symbol S2 0.157(6) 0.608(11) 0.500(8) -0.079(6) -0.140(5) 0.070(5) S S9 0.157(6) 0.608(11) 0.500(8) -0.079(6) -0.140(5) 0.070(5) S O7 0.157(6) 0.608(11) 0.500(8) -0.079(6) -0.140(5) 0.070(5) O C10 0.157(6) 0.608(11) 0.500(8) -0.079(6) -0.140(5) 0.070(5) N F5 0.157(6) 0.608(11) 0.500(8) -0.079(6) -0.140(5) 0.070(5) F F12 0.157(6) 0.608(11) 0.500(8) -0.079(6) -0.140(5) 0.070(5) F N1 0.157(6) 0.608(11) 0.500(8) 0.052(10) -0.140(5) 0.030(17) N O8 0.157(6) 0.608(11) 0.500(8) 0.052(10) -0.140(5) 0.030(17) O O15 0.157(6) 0.608(11) 0.500(8) 0.052(10) -0.140(5) 0.030(17) O C3 0.157(6) 0.608(11) 0.500(8) 0.052(10) -0.140(5) 0.030(17) N F4 0.157(6) 0.608(11) 0.500(8) 0.052(10) -0.140(5) 0.030(17) F F6 0.157(6) 0.608(11) 0.500(8) 0.052(10) -0.140(5) 0.030(17) F F11 0.157(6) 0.608(11) 0.500(8) 0.052(10) -0.140(5) 0.030(17) F F13 0.157(6) 0.608(11) 0.500(8) 0.052(10) -0.140(5) 0.030(17) F # Note: if the displacement parameters were refined anisotropically # the U matrices should be given as for single-crystal studies. #============================================================================= # 10. DISTANCES AND ANGLES / MOLECULAR GEOMETRY _geom_special_details ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag ? ? ? ? ? ? loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag ? ? ? ? ? ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag ? ? ? ? ? ? ? ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag ? ? ? ? ? ? ? ? ? ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_D _geom_hbond_site_symmetry_H _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag ? ? ? ? ? ? ? ? ? ? ? #============================================================================= #============================================================================= # Additional structures (last six sections and associated data_? identifiers) # may be added at this point. #============================================================================= # Attachment 'MH646-413K.cif' data_DABCO-triflimide_MH646 _database_code_depnum_ccdc_archive 'CCDC 797205' #TrackingRef 'MH646-413K.cif' #============================================================================= # 5. CHEMICAL DATA _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_iupac ? _chemical_formula_sum ? _chemical_formula_weight ? _chemical_melting_point ? _chemical_compound_source ? # for minerals and # natural products loop_ _atom_type_symbol _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source n 12.21260 0.00570 3.13220 9.89330 2.01250 28.99750 1.16630 0.58260 -11.52900 0.02900 0.01800 International_Tables_for_Crystallography_Vol.C(1991)_Tables_6.1.1.4_and_6.1.1.5 c 2.31000 20.84390 1.02000 10.20750 1.58860 0.56870 0.86500 51.65120 0.21560 0.01700 0.00900 International_Tables_for_Crystallography_Vol.C(1991)_Tables_6.1.1.4_and_6.1.1.5 s 6.90530 1.46790 5.20340 22.21510 1.43790 0.25360 1.58630 56.17200 0.86690 0.31900 0.55700 International_Tables_for_Crystallography_Vol.C(1991)_Tables_6.1.1.4_and_6.1.1.5 o 3.04850 13.27710 2.28680 5.70110 1.54630 0.32390 0.86700 32.90890 0.25080 0.04700 0.03200 International_Tables_for_Crystallography_Vol.C(1991)_Tables_6.1.1.4_and_6.1.1.5 f 3.53920 10.28250 2.64120 4.29440 1.51700 0.26150 1.02430 26.14760 0.27760 0.06900 0.05300 International_Tables_for_Crystallography_Vol.C(1991)_Tables_6.1.1.4_and_6.1.1.5 #============================================================================= # 6. POWDER SPECIMEN AND CRYSTAL DATA _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'C M C 21' _symmetry_space_group_name_Hall 'C 2c -2' loop_ _symmetry_equiv_pos_as_xyz #<--must include 'x,y,z' x,y,z -x,y,z x,-y,z+1/2 -x,-y,z+1/2 x+1/2,y+1/2,z -x+1/2,y+1/2,z x+1/2,-y+1/2,z+1/2 -x+1/2,-y+1/2,z+1/2 _cell_length_a 10.50402(6) _cell_length_b 21.83325(14) _cell_length_c 10.63527(6) _cell_angle_alpha 90.00000 _cell_angle_beta 90.00000 _cell_angle_gamma 90.00000 _cell_volume 2439.06(3) _cell_formula_units_Z ? _cell_measurement_temperature ? _cell_special_details ; ? ; # The next three fields give the specimen dimensions in mm. The equatorial # plane contains the incident and diffracted beam. _pd_spec_size_axial ? # perpendicular to # equatorial plane _pd_spec_size_equat ? # parallel to # scattering vector # in transmission _pd_spec_size_thick ? # parallel to # scattering vector # in reflection # The next five fields are character fields that describe the specimen. _pd_spec_mounting # This field should be # used to give details of the # container. ; ? ; _pd_spec_mount_mode ? # options are 'reflection' # or 'transmission' _pd_spec_shape ? # options are 'cylinder' # 'flat_sheet' or 'irregular' _pd_char_particle_morphology ? _pd_char_colour ? # use ICDD colour descriptions # The following three fields describe the preparation of the specimen. # The cooling rate is in K/min. The pressure at which the sample was # prepared is in kPa. The temperature of preparation is in K. _pd_prep_cool_rate ? _pd_prep_pressure ? _pd_prep_temperature ? # The next four fields are normally only needed for transmission experiments. _exptl_absorpt_coefficient_mu ? _exptl_absorpt_correction_type ? _exptl_absorpt_process_details ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? #============================================================================= # 7. EXPERIMENTAL DATA _exptl_special_details ; ? ; # The following item is used to identify the equipment used to record # the powder pattern when the diffractogram was measured at a laboratory # other than the authors' home institution, e.g. when neutron or synchrotron # radiation is used. _pd_instr_location ; ? ; _pd_calibration_special_details # description of the method used # to calibrate the instrument ; ? ; _diffrn_ambient_temperature ? _diffrn_source ? # _diffrn_radiation_type X-ray _diffrn_source_target ? # Put here the chemical symbol of the anode _diffrn_radiation_monochromator ? _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? # Not in version 2.0.1 _diffrn_detector ? _diffrn_detector_type ? # make or model of detector _pd_meas_scan_method ? # options are 'step', 'cont', # 'tof', 'fixed' or # 'disp' (= dispersive) _pd_meas_special_details ; ? ; # The following four items give details of the measured (not processed) # powder pattern. Angles are in degrees. _pd_meas_number_of_points 7495 _pd_meas_2theta_range_min 3.05400 _pd_meas_2theta_range_max 70.50000 _pd_meas_2theta_range_inc 0.009001 #============================================================================= # 8. REFINEMENT DATA _refine_special_details ; ? ; # Use the next field to give any special details about the fitting of the # powder pattern. _pd_proc_ls_special_details ; ? ; # The next three items are given as text. _pd_proc_ls_profile_function ? _pd_proc_ls_background_function ? _pd_proc_ls_pref_orient_corr ; ? ; # The following profile R-factors are NOT CORRECTED for background # The sum is extended to all non-excluded points. # These are the current CIF standard _pd_proc_ls_prof_R_factor 4.3502 _pd_proc_ls_prof_wR_factor 6.2783 _pd_proc_ls_prof_wR_expected 3.0658 # The following profile R-factors are CORRECTED for background # The sum is extended to all non-excluded points. # These items are not in the current CIF standard, but are defined above _pd_proc_ls_prof_cR_factor 17.8090 _pd_proc_ls_prof_cwR_factor 14.3811 _pd_proc_ls_prof_cwR_expected 7.0226 # The following items are not in the CIF standard, but are defined above _pd_proc_ls_prof_chi2 4.1936 _pd_proc_ls_prof_echi2 4.7908 # Items related to LS refinement _refine_ls_R_I_factor 5.6097 _refine_ls_number_reflns 334 _refine_ls_number_parameters 119 _refine_ls_number_restraints 80 # The following four items apply to angular dispersive measurements. # 2theta minimum, maximum and increment (in degrees) are for the # intensities used in the refinement. _pd_proc_2theta_range_min 3.0540 _pd_proc_2theta_range_max 70.5000 _pd_proc_2theta_range_inc 0.009001 _pd_proc_wavelength 1.540593 _pd_block_diffractogram_id ? # The id used for the block containing # the powder pattern profile (section 11) # Give appropriate details in the next two text fields. _pd_proc_info_excluded_regions ? _pd_proc_info_data_reduction ? # The following items are used to identify the programs used. _computing_data_collection ? _computing_structure_solution ? _computing_structure_refinement FULLPROF _computing_molecular_graphics ? _computing_publication_material ? #============================================================================= # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type # Not in version 2.0.1 _atom_site_type_symbol N1a 0.50000 0.7831(4) 0.1620(8) 0.043(6) 1.00000 Uiso N N3a 0.50000 0.8622(4) 0.3348(8) 0.043(6) 1.00000 Uiso N C4a 0.4444(15) 0.8407(4) 0.1172(12) 0.043(6) 0.50000 Uiso C C7a 0.4444(15) 0.8892(5) 0.2198(10) 0.043(6) 0.50000 Uiso C C10a 0.4203(16) 0.7609(7) 0.2682(12) 0.043(6) 0.50000 Uiso C C13a 0.4203(16) 0.8092(6) 0.3714(14) 0.043(6) 0.50000 Uiso C C16a 0.6303(8) 0.7911(11) 0.206(2) 0.043(6) 0.50000 Uiso C C19a 0.6303(8) 0.8390(12) 0.307(2) 0.043(6) 0.50000 Uiso C S23b 0.50000 0.3284(4) 0.1112(6) 0.149(8) 1.00000 Uani S S24b 0.50000 0.3230(4) 0.3663(8) 0.149(8) 1.00000 Uani S N25b 0.551(3) 0.3490(14) 0.2400(8) 0.149(8) 0.50000 Uani N O26b 0.450(4) 0.325(2) -0.0083(17) 0.149(8) 0.50000 Uani O O27b 0.577(3) 0.2879(16) 0.046(3) 0.149(8) 0.50000 Uani O O28b 0.543(4) 0.2753(13) 0.446(3) 0.149(8) 0.50000 Uani O O29b 0.3670(11) 0.318(2) 0.350(4) 0.149(8) 0.50000 Uani O C30b 0.4631(8) 0.4076(4) 0.0670(10) 0.149(8) 0.50000 Uani C C31b 0.50000 0.4008(3) 0.4280(8) 0.149(8) 1.00000 Uani C F32b 0.3413(12) 0.4201(16) 0.039(4) 0.149(8) 0.50000 Uani F F33b 0.538(3) 0.4410(15) -0.007(2) 0.149(8) 0.50000 Uani F F34b 0.426(2) 0.4446(12) 0.155(2) 0.149(8) 0.50000 Uani F F35b 0.3811(13) 0.3981(17) 0.395(3) 0.149(8) 0.50000 Uani F F36b 0.50000 0.3948(11) 0.5520(9) 0.149(8) 1.00000 Uani F F37b 0.532(3) 0.4556(7) 0.386(3) 0.149(8) 0.50000 Uani F S23c 0.6287(9) 0.1328(3) 0.2599(8) 0.310(11) 1.00000 Uani S N25c 0.50000 0.1081(19) 0.319(3) 0.310(11) 1.00000 Uani N O26c 0.647(3) 0.1318(11) 0.1298(10) 0.310(11) 1.00000 Uani O O27c 0.707(2) 0.1857(9) 0.277(3) 0.310(11) 1.00000 Uani O C30c 0.6735(9) 0.0519(4) 0.2605(9) 0.310(11) 1.00000 Uani C F32c 0.6979(20) 0.0429(11) 0.1401(10) 0.310(11) 1.00000 Uani F F33c 0.7957(8) 0.0582(10) 0.264(3) 0.310(11) 1.00000 Uani F F34c 0.6174(14) 0.0051(8) 0.3114(18) 0.310(11) 1.00000 Uani F loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 _atom_site_aniso_type_symbol S23b 0.068(8) 0.270(9) 0.109(7) 0.00000 0.00000 0.00000 S S24b 0.068(8) 0.270(9) 0.109(7) 0.00000 0.00000 0.00000 S N25b 0.068(8) 0.270(9) 0.109(7) 0.00000 0.00000 0.00000 N O26b 0.068(8) 0.270(9) 0.109(7) 0.00000 0.00000 0.00000 O O27b 0.068(8) 0.270(9) 0.109(7) 0.00000 0.00000 0.00000 O O28b 0.068(8) 0.270(9) 0.109(7) 0.00000 0.00000 0.00000 O O29b 0.068(8) 0.270(9) 0.109(7) 0.00000 0.00000 0.00000 O C30b 0.068(8) 0.270(9) 0.109(7) 0.00000 0.00000 0.00000 C C31b 0.068(8) 0.270(9) 0.109(7) 0.00000 0.00000 0.00000 C F32b 0.068(8) 0.270(9) 0.109(7) 0.00000 0.00000 0.00000 F F33b 0.068(8) 0.270(9) 0.109(7) 0.00000 0.00000 0.00000 F F34b 0.068(8) 0.270(9) 0.109(7) 0.00000 0.00000 0.00000 F F35b 0.068(8) 0.270(9) 0.109(7) 0.00000 0.00000 0.00000 F F36b 0.068(8) 0.270(9) 0.109(7) 0.00000 0.00000 0.00000 F F37b 0.068(8) 0.270(9) 0.109(7) 0.00000 0.00000 0.00000 F S23c 0.332(10) 0.298(12) 0.300(11) 0.00000 0.00000 0.00000 S N25c 0.332(10) 0.298(12) 0.300(11) 0.00000 0.00000 0.00000 N O26c 0.332(10) 0.298(12) 0.300(11) 0.00000 0.00000 0.00000 O O27c 0.332(10) 0.298(12) 0.300(11) 0.00000 0.00000 0.00000 O C30c 0.332(10) 0.298(12) 0.300(11) 0.00000 0.00000 0.00000 C F32c 0.332(10) 0.298(12) 0.300(11) 0.00000 0.00000 0.00000 F F33c 0.332(10) 0.298(12) 0.300(11) 0.00000 0.00000 0.00000 F F34c 0.332(10) 0.298(12) 0.300(11) 0.00000 0.00000 0.00000 F # Note: if the displacement parameters were refined anisotropically # the U matrices should be given as for single-crystal studies. #============================================================================= # 10. DISTANCES AND ANGLES / MOLECULAR GEOMETRY _geom_special_details ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag ? ? ? ? ? ? loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag ? ? ? ? ? ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag ? ? ? ? ? ? ? ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag ? ? ? ? ? ? ? ? ? ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_D _geom_hbond_site_symmetry_H _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag ? ? ? ? ? ? ? ? ? ? ? #============================================================================= #============================================================================= # Additional structures (last six sections and associated data_? identifiers) # may be added at this point. #============================================================================= # The following lines are used to test the character set of files sent by # network email or other means. They are not part of the CIF data set. # abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789 # !@#$%^&*()_+{}:"~<>?|\-=[];'`,./ # Attachment 'NH646-173K.cif' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2009-08-06 at 11:13:36 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : c:\wingx\files\archive.dat # CIF files read : mh646_2_archive data_mh646 _database_code_depnum_ccdc_archive 'CCDC 797206' #TrackingRef 'NH646-173K.cif' _audit_creation_date 2009-08-06T11:13:36-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C6 H14 N2, 2(C2 F6 N O4 S2)' _chemical_formula_sum 'C10 H14 F12 N4 O8 S4' _chemical_formula_weight 674.53 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _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 11.2776(2) _cell_length_b 23.3071(4) _cell_length_c 9.4153(2) _cell_angle_alpha 90 _cell_angle_beta 111.222(3) _cell_angle_gamma 90 _cell_volume 2306.96(8) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 10893 _cell_measurement_theta_min 2.9766 _cell_measurement_theta_max 28.4063 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description 'irregular fragment' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.2 _exptl_crystal_density_diffrn 1.942 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1352 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.556 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.24 (release 21-04-2008 CrysAlis171 .NET) (compiled Apr 21 2008,18:23:10) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.8081 _exptl_absorpt_correction_T_max 0.8969 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 10.3822 _diffrn_orient_matrix_ub_11 -0.0385695903 _diffrn_orient_matrix_ub_12 -0.0136986984 _diffrn_orient_matrix_ub_13 -0.0589204008 _diffrn_orient_matrix_ub_21 -0.0634019857 _diffrn_orient_matrix_ub_22 -0.004937552 _diffrn_orient_matrix_ub_23 0.0182395549 _diffrn_orient_matrix_ub_31 -0.0315993904 _diffrn_orient_matrix_ub_32 0.0266476691 _diffrn_orient_matrix_ub_33 -0.0269165761 _diffrn_measurement_device_type 'Oxford Diffraction Gemini-R Ultra' _diffrn_measurement_method '\w (1\% width)' _diffrn_reflns_av_R_equivalents 0.0268 _diffrn_reflns_av_unetI/netI 0.0221 _diffrn_reflns_number 16309 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.99 _diffrn_reflns_theta_max 25.35 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _reflns_number_total 4213 _reflns_number_gt 3669 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.24 (release 21-04-2008 CrysAlis171 .NET) (compiled Apr 21 2008,18:23:10) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.24 (release 21-04-2008 CrysAlis171 .NET) (compiled Apr 21 2008,18:23:10) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.24 (release 21-04-2008 CrysAlis171 .NET) (compiled Apr 21 2008,18:23:10) ; _computing_structure_solution 'SIR2002 (Burla et al., 2003)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0382P)^2^+1.3487P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 4213 _refine_ls_number_parameters 351 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0369 _refine_ls_R_factor_gt 0.0291 _refine_ls_wR_factor_ref 0.0738 _refine_ls_wR_factor_gt 0.0707 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.357 _refine_diff_density_min -0.363 _refine_diff_density_rms 0.055 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.22338(4) 0.179402(19) 0.87907(5) 0.01723(12) Uani 1 1 d . . . S2 S 0.17310(4) 0.061251(19) 0.85160(5) 0.01647(12) Uani 1 1 d . . . F4 F 0.29944(13) -0.03361(5) 0.89639(16) 0.0424(4) Uani 1 1 d . . . F3 F 0.41564(13) 0.23590(6) 0.86593(18) 0.0448(4) Uani 1 1 d . . . F2 F 0.46673(12) 0.16976(6) 1.03537(16) 0.0462(4) Uani 1 1 d . . . F5 F 0.41443(12) 0.04161(6) 0.92343(18) 0.0443(4) Uani 1 1 d . . . F6 F 0.34199(14) 0.01793(7) 1.09598(15) 0.0506(4) Uani 1 1 d . . . F1 F 0.41210(12) 0.14777(6) 0.79900(16) 0.0368(3) Uani 1 1 d . . . O1 O 0.15460(13) 0.18785(6) 0.72029(15) 0.0218(3) Uani 1 1 d . . . O4 O 0.16507(13) 0.06418(6) 0.69669(15) 0.0222(3) Uani 1 1 d . . . O2 O 0.21368(14) 0.22189(6) 0.98351(16) 0.0268(3) Uani 1 1 d . . . O3 O 0.07591(13) 0.03182(6) 0.88500(16) 0.0261(3) Uani 1 1 d . . . N3 N 0.20501(15) 0.11942(7) 0.94384(17) 0.0181(3) Uani 1 1 d . . . C7 C 0.3906(2) 0.18297(9) 0.8971(3) 0.0287(5) Uani 1 1 d . . . C8 C 0.3168(2) 0.01949(9) 0.9489(2) 0.0272(5) Uani 1 1 d . . . S3 S -0.17861(4) 0.17214(2) -0.27094(5) 0.01809(12) Uani 1 1 d . . . S4 S -0.23197(5) 0.06305(2) -0.39547(6) 0.02495(13) Uani 1 1 d . . . F9 F -0.32412(12) 0.19704(6) -0.11817(15) 0.0396(3) Uani 1 1 d . . . F10 F -0.39551(17) 0.12313(7) -0.61384(18) 0.0638(5) Uani 1 1 d . . . F8 F -0.29355(13) 0.26612(5) -0.25257(17) 0.0441(4) Uani 1 1 d . . . F12 F -0.41141(17) 0.03171(8) -0.64312(19) 0.0692(5) Uani 1 1 d . . . F11 F -0.47907(14) 0.07323(7) -0.4843(2) 0.0619(5) Uani 1 1 d . . . F7 F -0.42048(11) 0.19712(6) -0.36074(15) 0.0394(3) Uani 1 1 d . . . O5 O -0.17072(14) 0.19314(6) -0.40926(15) 0.0284(3) Uani 1 1 d . . . O6 O -0.07571(12) 0.18593(6) -0.13252(15) 0.0255(3) Uani 1 1 d . . . O8 O -0.14487(16) 0.07158(7) -0.47174(19) 0.0387(4) Uani 1 1 d . . . O7 O -0.24068(16) 0.00746(6) -0.33786(19) 0.0382(4) Uani 1 1 d . . . N4 N -0.22135(16) 0.10835(7) -0.26840(19) 0.0224(4) Uani 1 1 d . . . C9 C -0.31281(19) 0.21020(9) -0.2496(2) 0.0274(5) Uani 1 1 d . . . C10 C -0.3892(2) 0.07394(11) -0.5428(3) 0.0427(6) Uani 1 1 d . . . N1 N 0.06322(16) 0.12237(7) 0.42119(18) 0.0180(3) Uani 1 1 d . . . N2 N 0.06408(16) 0.14482(7) 0.16496(19) 0.0188(4) Uani 1 1 d . . . C1 C 0.19765(19) 0.12850(9) 0.4309(2) 0.0242(4) Uani 1 1 d . . . H1A H 0.2424 0.0913 0.4584 0.029 Uiso 1 1 calc R . . H1B H 0.2427 0.1569 0.5102 0.029 Uiso 1 1 calc R . . C4 C 0.0143(2) 0.08541(8) 0.1629(2) 0.0248(5) Uani 1 1 d . . . H4A H 0.0742 0.0572 0.1475 0.03 Uiso 1 1 calc R . . H4B H -0.0688 0.0813 0.0785 0.03 Uiso 1 1 calc R . . C3 C -0.0008(2) 0.07461(8) 0.3151(2) 0.0229(4) Uani 1 1 d . . . H3A H -0.0922 0.0732 0.3009 0.027 Uiso 1 1 calc R . . H3B H 0.0384 0.0374 0.358 0.027 Uiso 1 1 calc R . . C2 C 0.1968(2) 0.14820(10) 0.2770(2) 0.0274(5) Uani 1 1 d . . . H2A H 0.2283 0.1881 0.2841 0.033 Uiso 1 1 calc R . . H2B H 0.2532 0.1234 0.2439 0.033 Uiso 1 1 calc R . . C5 C -0.0073(2) 0.17711(8) 0.3685(2) 0.0223(4) Uani 1 1 d . . . H5A H 0.0389 0.2093 0.4338 0.027 Uiso 1 1 calc R . . H5B H -0.093 0.1745 0.3745 0.027 Uiso 1 1 calc R . . C6 C -0.0184(2) 0.18724(9) 0.2045(2) 0.0254(5) Uani 1 1 d . . . H6A H -0.1079 0.1826 0.1352 0.03 Uiso 1 1 calc R . . H6B H 0.0091 0.2268 0.193 0.03 Uiso 1 1 calc R . . H1N H 0.061(2) 0.1142(9) 0.506(3) 0.023(6) Uiso 1 1 d . . . H2N H 0.061(2) 0.1530(9) 0.078(3) 0.019(6) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0180(2) 0.0180(2) 0.0170(2) -0.00101(18) 0.00787(19) 0.00032(18) S2 0.0181(2) 0.0177(2) 0.0142(2) 0.00134(17) 0.00642(18) 0.00129(18) F4 0.0439(8) 0.0203(7) 0.0579(9) 0.0013(6) 0.0121(7) 0.0098(6) F3 0.0357(7) 0.0297(7) 0.0745(10) -0.0004(7) 0.0263(7) -0.0116(6) F2 0.0237(7) 0.0590(9) 0.0441(9) 0.0010(7) -0.0021(6) -0.0016(6) F5 0.0228(7) 0.0372(8) 0.0727(10) 0.0165(7) 0.0171(7) 0.0099(6) F6 0.0561(9) 0.0610(10) 0.0242(7) 0.0146(6) 0.0018(7) 0.0220(7) F1 0.0294(7) 0.0382(7) 0.0525(8) -0.0062(6) 0.0266(6) -0.0011(6) O1 0.0261(7) 0.0215(7) 0.0187(7) 0.0040(5) 0.0092(6) 0.0020(6) O4 0.0306(8) 0.0216(7) 0.0149(7) -0.0003(5) 0.0088(6) 0.0036(6) O2 0.0343(8) 0.0226(7) 0.0250(8) -0.0053(6) 0.0125(6) 0.0024(6) O3 0.0277(8) 0.0257(8) 0.0292(8) -0.0010(6) 0.0155(7) -0.0060(6) N3 0.0209(8) 0.0209(8) 0.0142(8) -0.0007(6) 0.0083(7) -0.0004(7) C7 0.0221(10) 0.0263(11) 0.0372(13) -0.0023(9) 0.0103(10) -0.0042(9) C8 0.0276(11) 0.0247(11) 0.0270(12) 0.0062(8) 0.0071(9) 0.0059(9) S3 0.0170(2) 0.0228(3) 0.0149(2) 0.00197(18) 0.00621(19) -0.00023(18) S4 0.0283(3) 0.0240(3) 0.0267(3) -0.0026(2) 0.0151(2) 0.0006(2) F9 0.0326(7) 0.0562(9) 0.0382(8) -0.0054(6) 0.0226(6) 0.0045(6) F10 0.0618(11) 0.0601(11) 0.0418(9) 0.0131(8) -0.0144(8) -0.0052(8) F8 0.0403(8) 0.0236(7) 0.0626(9) -0.0033(6) 0.0118(7) 0.0058(6) F12 0.0723(12) 0.0681(12) 0.0530(10) -0.0328(9) 0.0056(9) -0.0177(9) F11 0.0285(8) 0.0711(11) 0.0818(12) -0.0131(9) 0.0149(8) -0.0069(7) F7 0.0184(6) 0.0446(8) 0.0444(8) -0.0049(6) -0.0016(6) 0.0048(5) O5 0.0350(8) 0.0324(8) 0.0190(7) 0.0033(6) 0.0113(6) -0.0081(6) O6 0.0182(7) 0.0371(8) 0.0191(7) -0.0012(6) 0.0041(6) 0.0006(6) O8 0.0430(9) 0.0456(10) 0.0394(9) -0.0091(7) 0.0293(8) -0.0036(8) O7 0.0497(10) 0.0211(8) 0.0500(10) -0.0010(7) 0.0255(9) 0.0023(7) N4 0.0294(9) 0.0212(9) 0.0219(9) 0.0027(7) 0.0154(8) 0.0014(7) C9 0.0222(10) 0.0263(11) 0.0315(12) -0.0039(9) 0.0068(9) 0.0015(8) C10 0.0402(14) 0.0418(15) 0.0390(14) -0.0098(11) 0.0056(12) -0.0091(11) N1 0.0273(9) 0.0181(8) 0.0121(8) 0.0021(6) 0.0115(7) 0.0023(7) N2 0.0294(9) 0.0187(8) 0.0120(8) 0.0017(6) 0.0118(7) 0.0008(7) C1 0.0238(10) 0.0315(12) 0.0177(10) -0.0009(8) 0.0079(8) 0.0021(8) C4 0.0403(12) 0.0174(10) 0.0201(10) -0.0027(8) 0.0150(9) -0.0057(9) C3 0.0341(11) 0.0172(10) 0.0218(10) -0.0010(8) 0.0156(9) -0.0039(8) C2 0.0247(11) 0.0402(13) 0.0202(11) -0.0011(9) 0.0114(9) -0.0029(9) C5 0.0328(11) 0.0177(10) 0.0201(10) 0.0017(8) 0.0140(9) 0.0068(8) C6 0.0375(12) 0.0217(10) 0.0194(10) 0.0036(8) 0.0131(9) 0.0101(9) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O1 1.4269(14) . ? S1 O2 1.4274(14) . ? S1 N3 1.5685(16) . ? S1 C7 1.833(2) . ? S2 O3 1.4214(14) . ? S2 O4 1.4298(14) . ? S2 N3 1.5798(16) . ? S2 C8 1.827(2) . ? F4 C8 1.321(2) . ? F3 C7 1.322(2) . ? F2 C7 1.310(3) . ? F5 C8 1.314(3) . ? F6 C8 1.309(2) . ? F1 C7 1.322(3) . ? S3 O5 1.4240(14) . ? S3 O6 1.4330(14) . ? S3 N4 1.5659(17) . ? S3 C9 1.827(2) . ? S4 O7 1.4217(16) . ? S4 O8 1.4250(16) . ? S4 N4 1.5673(17) . ? S4 C10 1.831(3) . ? F9 C9 1.325(3) . ? F10 C10 1.316(3) . ? F8 C9 1.323(2) . ? F12 C10 1.323(3) . ? F11 C10 1.317(3) . ? F7 C9 1.320(2) . ? N1 C5 1.490(2) . ? N1 C1 1.492(3) . ? N1 C3 1.495(2) . ? N1 H1N 0.83(2) . ? N2 C2 1.489(3) . ? N2 C4 1.492(2) . ? N2 C6 1.494(2) . ? N2 H2N 0.83(2) . ? C1 C2 1.516(3) . ? C1 H1A 0.99 . ? C1 H1B 0.99 . ? C4 C3 1.524(3) . ? C4 H4A 0.99 . ? C4 H4B 0.99 . ? C3 H3A 0.99 . ? C3 H3B 0.99 . ? C2 H2A 0.99 . ? C2 H2B 0.99 . ? C5 C6 1.522(3) . ? C5 H5A 0.99 . ? C5 H5B 0.99 . ? C6 H6A 0.99 . ? C6 H6B 0.99 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 S1 O2 118.54(8) . . ? O1 S1 N3 115.61(8) . . ? O2 S1 N3 107.25(9) . . ? O1 S1 C7 103.99(9) . . ? O2 S1 C7 103.74(9) . . ? N3 S1 C7 106.29(9) . . ? O3 S2 O4 118.66(8) . . ? O3 S2 N3 109.45(9) . . ? O4 S2 N3 115.94(8) . . ? O3 S2 C8 104.30(9) . . ? O4 S2 C8 104.72(9) . . ? N3 S2 C8 101.39(9) . . ? S1 N3 S2 125.95(10) . . ? F2 C7 F1 109.19(18) . . ? F2 C7 F3 108.91(17) . . ? F1 C7 F3 108.43(19) . . ? F2 C7 S1 111.31(16) . . ? F1 C7 S1 110.47(14) . . ? F3 C7 S1 108.47(14) . . ? F6 C8 F5 109.17(18) . . ? F6 C8 F4 108.42(17) . . ? F5 C8 F4 108.64(18) . . ? F6 C8 S2 111.02(15) . . ? F5 C8 S2 110.43(14) . . ? F4 C8 S2 109.10(14) . . ? O5 S3 O6 117.16(9) . . ? O5 S3 N4 117.51(9) . . ? O6 S3 N4 110.59(9) . . ? O5 S3 C9 105.20(10) . . ? O6 S3 C9 102.79(9) . . ? N4 S3 C9 100.80(10) . . ? O7 S4 O8 118.35(10) . . ? O7 S4 N4 108.62(10) . . ? O8 S4 N4 114.50(9) . . ? O7 S4 C10 103.51(11) . . ? O8 S4 C10 104.71(12) . . ? N4 S4 C10 105.70(11) . . ? S3 N4 S4 124.53(11) . . ? F7 C9 F8 108.76(17) . . ? F7 C9 F9 108.36(18) . . ? F8 C9 F9 108.64(17) . . ? F7 C9 S3 111.20(14) . . ? F8 C9 S3 109.09(15) . . ? F9 C9 S3 110.73(14) . . ? F10 C10 F11 108.4(2) . . ? F10 C10 F12 108.9(2) . . ? F11 C10 F12 108.3(2) . . ? F10 C10 S4 111.41(17) . . ? F11 C10 S4 111.22(18) . . ? F12 C10 S4 108.59(18) . . ? C5 N1 C1 110.27(15) . . ? C5 N1 C3 110.14(15) . . ? C1 N1 C3 110.28(15) . . ? C5 N1 H1N 108.7(15) . . ? C1 N1 H1N 110.1(16) . . ? C3 N1 H1N 107.2(15) . . ? C2 N2 C4 109.61(16) . . ? C2 N2 C6 110.20(16) . . ? C4 N2 C6 110.62(16) . . ? C2 N2 H2N 111.3(15) . . ? C4 N2 H2N 108.6(15) . . ? C6 N2 H2N 106.5(15) . . ? N1 C1 C2 108.41(16) . . ? N1 C1 H1A 110 . . ? C2 C1 H1A 110 . . ? N1 C1 H1B 110 . . ? C2 C1 H1B 110 . . ? H1A C1 H1B 108.4 . . ? N2 C4 C3 108.11(15) . . ? N2 C4 H4A 110.1 . . ? C3 C4 H4A 110.1 . . ? N2 C4 H4B 110.1 . . ? C3 C4 H4B 110.1 . . ? H4A C4 H4B 108.4 . . ? N1 C3 C4 108.27(15) . . ? N1 C3 H3A 110 . . ? C4 C3 H3A 110 . . ? N1 C3 H3B 110 . . ? C4 C3 H3B 110 . . ? H3A C3 H3B 108.4 . . ? N2 C2 C1 108.54(16) . . ? N2 C2 H2A 110 . . ? C1 C2 H2A 110 . . ? N2 C2 H2B 110 . . ? C1 C2 H2B 110 . . ? H2A C2 H2B 108.4 . . ? N1 C5 C6 107.96(15) . . ? N1 C5 H5A 110.1 . . ? C6 C5 H5A 110.1 . . ? N1 C5 H5B 110.1 . . ? C6 C5 H5B 110.1 . . ? H5A C5 H5B 108.4 . . ? N2 C6 C5 108.69(15) . . ? N2 C6 H6A 110 . . ? C5 C6 H6A 110 . . ? N2 C6 H6B 110 . . ? C5 C6 H6B 110 . . ? H6A C6 H6B 108.3 . . ? 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 S1 N3 S2 28.69(16) . . . . ? O2 S1 N3 S2 163.41(12) . . . . ? C7 S1 N3 S2 -86.10(14) . . . . ? O3 S2 N3 S1 -135.19(12) . . . . ? O4 S2 N3 S1 2.32(16) . . . . ? C8 S2 N3 S1 115.04(13) . . . . ? O1 S1 C7 F2 -173.17(14) . . . . ? O2 S1 C7 F2 62.22(16) . . . . ? N3 S1 C7 F2 -50.71(17) . . . . ? O1 S1 C7 F1 -51.69(16) . . . . ? O2 S1 C7 F1 -176.30(14) . . . . ? N3 S1 C7 F1 70.77(16) . . . . ? O1 S1 C7 F3 67.02(16) . . . . ? O2 S1 C7 F3 -57.59(17) . . . . ? N3 S1 C7 F3 -170.52(14) . . . . ? O3 S2 C8 F6 -60.44(17) . . . . ? O4 S2 C8 F6 174.21(15) . . . . ? N3 S2 C8 F6 53.26(17) . . . . ? O3 S2 C8 F5 178.33(14) . . . . ? O4 S2 C8 F5 52.98(17) . . . . ? N3 S2 C8 F5 -67.97(17) . . . . ? O3 S2 C8 F4 58.99(17) . . . . ? O4 S2 C8 F4 -66.37(16) . . . . ? N3 S2 C8 F4 172.68(14) . . . . ? O5 S3 N4 S4 11.67(17) . . . . ? O6 S3 N4 S4 -126.52(12) . . . . ? C9 S3 N4 S4 125.27(13) . . . . ? O7 S4 N4 S3 165.06(12) . . . . ? O8 S4 N4 S3 30.30(17) . . . . ? C10 S4 N4 S3 -84.40(16) . . . . ? O5 S3 C9 F7 63.86(17) . . . . ? O6 S3 C9 F7 -173.00(15) . . . . ? N4 S3 C9 F7 -58.76(17) . . . . ? O5 S3 C9 F8 -56.09(16) . . . . ? O6 S3 C9 F8 67.05(16) . . . . ? N4 S3 C9 F8 -178.71(14) . . . . ? O5 S3 C9 F9 -175.60(14) . . . . ? O6 S3 C9 F9 -52.46(16) . . . . ? N4 S3 C9 F9 61.78(16) . . . . ? O7 S4 C10 F10 -176.98(18) . . . . ? O8 S4 C10 F10 -52.4(2) . . . . ? N4 S4 C10 F10 68.9(2) . . . . ? O7 S4 C10 F11 62.01(19) . . . . ? O8 S4 C10 F11 -173.38(17) . . . . ? N4 S4 C10 F11 -52.1(2) . . . . ? O7 S4 C10 F12 -57.0(2) . . . . ? O8 S4 C10 F12 67.6(2) . . . . ? N4 S4 C10 F12 -171.16(18) . . . . ? C5 N1 C1 C2 -55.5(2) . . . . ? C3 N1 C1 C2 66.4(2) . . . . ? C2 N2 C4 C3 68.0(2) . . . . ? C6 N2 C4 C3 -53.8(2) . . . . ? C5 N1 C3 C4 68.0(2) . . . . ? C1 N1 C3 C4 -54.0(2) . . . . ? N2 C4 C3 N1 -11.1(2) . . . . ? C4 N2 C2 C1 -55.7(2) . . . . ? C6 N2 C2 C1 66.3(2) . . . . ? N1 C1 C2 N2 -9.5(2) . . . . ? C1 N1 C5 C6 66.8(2) . . . . ? C3 N1 C5 C6 -55.1(2) . . . . ? C2 N2 C6 C5 -54.7(2) . . . . ? C4 N2 C6 C5 66.6(2) . . . . ? N1 C5 C6 N2 -9.8(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1N O4 0.83(2) 2.10(2) 2.780(2) 139(2) . N1 H1N O1 0.83(2) 2.57(2) 3.037(2) 117.1(18) . N1 H1N O8 0.83(2) 2.61(2) 3.104(2) 120.1(18) 1_556 N2 H2N O6 0.83(2) 2.16(2) 2.838(2) 138.7(19) . N2 H2N N3 0.83(2) 2.52(2) 3.099(2) 128.0(18) 1_554