# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_Compound_1,3-IBn/OTf _database_code_depnum_ccdc_archive 'CCDC 886241' #TrackingRef 'knim.cif' #=================================================================== #=================================================================== # 5. CHEMICAL DATA #=================================================================== _chemical_name_systematic ; ; _chemical_name_common ? _chemical_formula_moiety 'C26 H24 I2 N6, 2(C F3 O3 S)' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C28 H24 F6 I2 N6 O6 S2' _chemical_formula_weight 972.47 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=================================================================== # 6. CRYSTAL DATA #=================================================================== _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 21/c' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,1/2+y,1/2-z 3 -x,-y,-z 4 x,1/2-y,1/2+z _cell_length_a 10.2000(2) _cell_length_b 28.2919(6) _cell_length_c 12.0816(2) _cell_angle_alpha 90 _cell_angle_beta 101.2130(8) _cell_angle_gamma 90 _cell_volume 3419.92(11) _cell_formula_units_Z 4 _cell_measurement_temperature 123(1) _cell_measurement_reflns_used 9689 _cell_measurement_theta_min 1.44 _cell_measurement_theta_max 25.44 _exptl_crystal_description column _exptl_crystal_colour colorless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.889 _exptl_crystal_density_method none _exptl_crystal_F_000 1896 _exptl_absorpt_coefficient_mu 2.045 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6173 _exptl_absorpt_correction_T_max 0.7452 _exptl_absorpt_process_details 'SADABS, Bruker, 2008b' _exptl_special_details ; Diffractometer operator E. Herdtweck scanspeed 10 s per frame dx 55 3278 frames measured in 7 data sets phi-scan with delta_phi = 0.50 omega-scans with delta_omega = 0.50 ; _diffrn_ambient_temperature 123(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'rotating anode FR591' _diffrn_radiation_monochromator graphite _diffrn_measurement_device ' \k-geometry diffractometer ' _diffrn_measurement_device_type ' Bruker APEX-II CCD ' _diffrn_measurement_method ' phi- and omega-rotation ' _diffrn_detector ' CCD plate ' _diffrn_detector_area_resol_mean 16 # 8 for binned mode _diffrn_standards_decay_% 0 # number of measured reflections (redundant set) _diffrn_reflns_number 64186 _diffrn_reflns_av_R_equivalents 0.0262 _diffrn_reflns_av_sigmaI/netI 0.0115 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -34 _diffrn_reflns_limit_k_max 34 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.44 _diffrn_reflns_theta_max 25.44 _reflns_number_total 6311 _reflns_number_gt 6137 # number of observed reflections (> n sig(I)) _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX II Control Software (Bruker, 2008a)' _computing_cell_refinement 'SAINT (Bruker, 2008b)' _computing_data_reduction 'SAINT (Bruker, 2008b)' _computing_structure_solution 'SIR92 (Altomare, 1994)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1998)' _computing_molecular_graphics 'PLATON (Spek, 2010)' _computing_publication_material 'PLATON (Spek, 2010)' #=================================================================== # 8. REFINEMENT DATA #=================================================================== _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating R_factor_obs 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 sigma _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0175P)^2^+6.2834P] 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_number_reflns 6311 _refine_ls_number_parameters 453 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0230 _refine_ls_R_factor_gt 0.0223 _refine_ls_wR_factor_ref 0.0530 _refine_ls_wR_factor_gt 0.0526 _refine_ls_goodness_of_fit_ref 1.107 _refine_ls_restrained_S_all 1.107 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.44 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.509 _refine_diff_density_min -0.693 _refine_diff_density_rms 0.067 #=================================================================== # 9. ATOMIC COORDINATES AND THERMAL PARAMETERS #=================================================================== loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags I1 I Uani 0.33569(2) 0.06240(1) 0.39307(1) 1.000 0.0229(1) . . I2 I Uani 0.10928(2) 0.07740(1) 1.08479(1) 1.000 0.0278(1) . . N1 N Uani 0.5131(2) 0.14076(7) 0.50935(17) 1.000 0.0197(6) . . N2 N Uani 0.5532(2) 0.16508(7) 0.60363(18) 1.000 0.0211(6) . . N3 N Uani 0.47556(19) 0.14967(7) 0.67213(17) 1.000 0.0183(6) . . N4 N Uani -0.0585(2) 0.16142(7) 0.97800(17) 1.000 0.0201(6) . . N5 N Uani -0.1070(2) 0.18350(7) 0.88201(18) 1.000 0.0212(6) . . N6 N Uani -0.05064(19) 0.16161(7) 0.80670(17) 1.000 0.0189(6) . . C1 C Uani 0.3874(2) 0.11614(8) 0.6239(2) 1.000 0.0177(7) . . C2 C Uani 0.4134(2) 0.11010(8) 0.5168(2) 1.000 0.0186(7) . . C3 C Uani 0.5005(3) 0.16830(9) 0.7879(2) 1.000 0.0252(8) . . C4 C Uani 0.5838(3) 0.14858(9) 0.4149(2) 1.000 0.0244(8) . . C5 C Uani 0.7169(2) 0.12319(9) 0.4339(2) 1.000 0.0212(7) . . C6 C Uani 0.8229(3) 0.14340(10) 0.3935(2) 1.000 0.0259(8) . . C7 C Uani 0.9455(3) 0.12049(10) 0.4079(2) 1.000 0.0298(8) . . C8 C Uani 0.9636(3) 0.07792(10) 0.4649(2) 1.000 0.0284(8) . . C9 C Uani 0.8591(3) 0.05767(9) 0.5060(2) 1.000 0.0258(8) . . C10 C Uani 0.7353(3) 0.07993(9) 0.4889(2) 1.000 0.0229(7) . . C11 C Uani 0.2890(2) 0.09298(9) 0.68064(19) 1.000 0.0179(7) . . C12 C Uani 0.2791(2) 0.04356(9) 0.6800(2) 1.000 0.0204(7) . . C13 C Uani 0.1853(3) 0.02171(9) 0.7321(2) 1.000 0.0228(7) . . C14 C Uani 0.1027(2) 0.04839(9) 0.7866(2) 1.000 0.0215(7) . . C15 C Uani 0.1138(2) 0.09736(9) 0.7882(2) 1.000 0.0187(7) . . C16 C Uani 0.2060(2) 0.12000(9) 0.73468(19) 1.000 0.0180(7) . . C17 C Uani 0.0331(2) 0.12613(8) 0.8519(2) 1.000 0.0182(7) . . C18 C Uani 0.0260(2) 0.12574(9) 0.9641(2) 1.000 0.0206(7) . . C19 C Uani -0.0909(3) 0.17454(9) 0.6874(2) 1.000 0.0235(7) . . C20 C Uani -0.0917(3) 0.18032(10) 1.0838(2) 1.000 0.0270(8) . . C21 C Uani -0.2372(3) 0.17420(9) 1.0886(2) 1.000 0.0234(7) . . C22 C Uani -0.2873(3) 0.13050(10) 1.1088(3) 1.000 0.0336(9) . . C23 C Uani -0.4204(3) 0.12559(11) 1.1182(3) 1.000 0.0383(10) . . C24 C Uani -0.5031(3) 0.16461(12) 1.1085(2) 1.000 0.0364(10) . . C25 C Uani -0.4539(3) 0.20830(12) 1.0880(3) 1.000 0.0418(10) . . C26 C Uani -0.3213(3) 0.21299(10) 1.0773(3) 1.000 0.0322(9) . . S1 S Uani 0.70023(6) 0.04280(2) 0.78879(5) 1.000 0.0184(2) . . F1 F Uani 0.51965(18) 0.05597(6) 0.91315(15) 1.000 0.0385(6) . . F2 F Uani 0.6966(2) 0.01969(7) 0.99832(14) 1.000 0.0511(7) . . F3 F Uani 0.5523(2) -0.01675(6) 0.87389(18) 1.000 0.0509(7) . . O1 O Uani 0.78700(18) 0.00334(7) 0.77819(15) 1.000 0.0268(6) . . O2 O Uani 0.59103(19) 0.04836(7) 0.69332(16) 1.000 0.0333(6) . . O3 O Uani 0.7651(2) 0.08582(7) 0.8303(2) 1.000 0.0442(8) . . C27 C Uani 0.6130(3) 0.02455(10) 0.8997(2) 1.000 0.0313(8) . . S2 S Uani 0.23098(6) 0.22437(2) 0.32181(5) 1.000 0.0233(2) . . F4 F Uani 0.2525(2) 0.20646(7) 0.53755(15) 1.000 0.0492(7) . . F5 F Uani 0.05497(17) 0.22792(6) 0.45519(16) 1.000 0.0392(6) . . F6 F Uani 0.21117(18) 0.27934(6) 0.49363(15) 1.000 0.0399(6) . . O4 O Uani 0.1602(2) 0.26131(8) 0.25290(18) 1.000 0.0420(7) . . O5 O Uani 0.1841(2) 0.17729(7) 0.29345(18) 1.000 0.0372(7) . . O6 O Uani 0.3742(2) 0.22959(8) 0.34691(19) 1.000 0.0379(7) . . C28 C Uani 0.1852(3) 0.23488(9) 0.4587(2) 1.000 0.0278(8) . . H31 H Uiso 0.59570 0.17560 0.81180 1.000 0.0380 calc R H32 H Uiso 0.47450 0.14460 0.83880 1.000 0.0380 calc R H33 H Uiso 0.44790 0.19710 0.79040 1.000 0.0380 calc R H41 H Uiso 0.59860 0.18290 0.40670 1.000 0.0290 calc R H42 H Uiso 0.52730 0.13710 0.34390 1.000 0.0290 calc R H61 H Uiso 0.81120 0.17300 0.35580 1.000 0.0310 calc R H71 H Uiso 1.01680 0.13410 0.37860 1.000 0.0360 calc R H81 H Uiso 1.04790 0.06250 0.47600 1.000 0.0340 calc R H91 H Uiso 0.87210 0.02860 0.54580 1.000 0.0310 calc R H101 H Uiso 0.66290 0.06550 0.51510 1.000 0.0270 calc R H121 H Uiso 0.33630 0.02510 0.64400 1.000 0.0240 calc R H131 H Uiso 0.17760 -0.01180 0.73050 1.000 0.0270 calc R H141 H Uiso 0.03920 0.03330 0.82270 1.000 0.0260 calc R H161 H Uiso 0.21210 0.15350 0.73510 1.000 0.0220 calc R H191 H Uiso -0.17980 0.18900 0.67460 1.000 0.0350 calc R H192 H Uiso -0.09320 0.14610 0.64060 1.000 0.0350 calc R H193 H Uiso -0.02650 0.19710 0.66730 1.000 0.0350 calc R H201 H Uiso -0.06890 0.21440 1.09000 1.000 0.0320 calc R H202 H Uiso -0.03660 0.16390 1.14900 1.000 0.0320 calc R H221 H Uiso -0.23070 0.10360 1.11630 1.000 0.0400 calc R H231 H Uiso -0.45450 0.09530 1.13140 1.000 0.0460 calc R H241 H Uiso -0.59370 0.16130 1.11580 1.000 0.0440 calc R H251 H Uiso -0.51040 0.23530 1.08120 1.000 0.0500 calc R H261 H Uiso -0.28800 0.24320 1.06200 1.000 0.0390 calc R loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I1 0.0216(1) 0.0275(1) 0.0191(1) -0.0031(1) 0.0031(1) -0.0011(1) I2 0.0279(1) 0.0339(1) 0.0207(1) 0.0053(1) 0.0024(1) 0.0060(1) N1 0.0172(10) 0.0209(10) 0.0217(10) 0.0038(8) 0.0059(8) 0.0030(8) N2 0.0198(10) 0.0193(10) 0.0250(11) -0.0005(8) 0.0064(8) 0.0011(8) N3 0.0169(10) 0.0171(10) 0.0216(10) -0.0004(8) 0.0056(8) 0.0015(8) N4 0.0179(10) 0.0230(11) 0.0197(10) -0.0034(8) 0.0041(8) -0.0004(8) N5 0.0183(10) 0.0213(11) 0.0242(11) -0.0034(9) 0.0044(8) -0.0002(8) N6 0.0158(10) 0.0196(10) 0.0211(10) 0.0003(8) 0.0035(8) -0.0016(8) C1 0.0164(11) 0.0163(11) 0.0204(12) 0.0004(9) 0.0035(9) 0.0039(9) C2 0.0163(11) 0.0179(12) 0.0214(12) 0.0007(9) 0.0033(9) 0.0033(9) C3 0.0237(13) 0.0275(14) 0.0246(13) -0.0076(11) 0.0053(10) -0.0037(11) C4 0.0243(13) 0.0284(14) 0.0227(13) 0.0063(10) 0.0097(10) 0.0017(11) C5 0.0202(12) 0.0270(13) 0.0171(12) -0.0011(10) 0.0055(9) -0.0014(10) C6 0.0274(14) 0.0297(14) 0.0222(13) 0.0027(11) 0.0087(11) -0.0053(11) C7 0.0228(13) 0.0393(16) 0.0302(14) -0.0051(12) 0.0124(11) -0.0093(11) C8 0.0185(13) 0.0333(15) 0.0333(15) -0.0086(12) 0.0051(11) 0.0003(11) C9 0.0239(13) 0.0239(13) 0.0298(14) -0.0023(11) 0.0059(11) 0.0005(10) C10 0.0207(12) 0.0238(13) 0.0257(13) -0.0002(10) 0.0081(10) -0.0030(10) C11 0.0152(11) 0.0211(12) 0.0167(11) -0.0003(9) 0.0017(9) -0.0008(9) C12 0.0195(12) 0.0206(12) 0.0206(12) -0.0021(10) 0.0025(9) 0.0010(10) C13 0.0257(13) 0.0169(12) 0.0250(13) 0.0001(10) 0.0032(10) -0.0020(10) C14 0.0192(12) 0.0230(13) 0.0220(12) 0.0010(10) 0.0036(10) -0.0036(10) C15 0.0156(11) 0.0223(12) 0.0174(11) -0.0004(9) 0.0015(9) 0.0018(9) C16 0.0163(11) 0.0183(12) 0.0183(12) 0.0013(9) 0.0009(9) 0.0005(9) C17 0.0142(11) 0.0194(12) 0.0211(12) 0.0007(9) 0.0037(9) -0.0025(9) C18 0.0164(11) 0.0238(12) 0.0208(12) 0.0002(10) 0.0020(9) -0.0009(9) C19 0.0217(12) 0.0266(13) 0.0208(12) 0.0037(10) 0.0005(10) 0.0011(10) C20 0.0261(13) 0.0326(15) 0.0225(13) -0.0087(11) 0.0052(11) 0.0005(11) C21 0.0275(13) 0.0260(13) 0.0172(12) -0.0051(10) 0.0059(10) -0.0001(10) C22 0.0401(16) 0.0246(14) 0.0381(16) -0.0025(12) 0.0124(13) 0.0027(12) C23 0.0483(18) 0.0336(16) 0.0363(16) -0.0031(13) 0.0165(14) -0.0145(14) C24 0.0286(15) 0.0502(19) 0.0328(16) -0.0101(14) 0.0122(12) -0.0053(13) C25 0.0289(15) 0.0387(17) 0.057(2) -0.0076(15) 0.0067(14) 0.0064(13) C26 0.0304(15) 0.0257(14) 0.0403(16) -0.0006(12) 0.0061(12) -0.0011(11) S1 0.0172(3) 0.0170(3) 0.0217(3) 0.0013(2) 0.0056(2) -0.0021(2) F1 0.0400(10) 0.0412(10) 0.0385(10) -0.0013(8) 0.0183(8) 0.0081(8) F2 0.0700(14) 0.0588(12) 0.0238(9) 0.0055(8) 0.0074(9) 0.0247(10) F3 0.0669(13) 0.0329(10) 0.0641(13) -0.0022(9) 0.0403(11) -0.0176(9) O1 0.0245(9) 0.0283(10) 0.0270(10) 0.0030(8) 0.0037(7) 0.0049(8) O2 0.0278(10) 0.0448(12) 0.0274(10) 0.0073(9) 0.0060(8) 0.0106(9) O3 0.0376(12) 0.0298(11) 0.0684(16) -0.0105(11) 0.0183(11) -0.0119(9) C27 0.0401(16) 0.0272(14) 0.0290(14) -0.0001(11) 0.0128(12) 0.0003(12) S2 0.0238(3) 0.0197(3) 0.0268(3) 0.0037(2) 0.0062(3) 0.0014(2) F4 0.0657(13) 0.0534(12) 0.0305(9) 0.0133(8) 0.0145(9) 0.0338(10) F5 0.0338(9) 0.0368(9) 0.0523(11) -0.0018(8) 0.0216(8) 0.0008(7) F6 0.0409(10) 0.0316(9) 0.0468(10) -0.0134(8) 0.0074(8) 0.0029(7) O4 0.0495(13) 0.0394(12) 0.0376(12) 0.0156(10) 0.0100(10) 0.0171(10) O5 0.0454(12) 0.0284(11) 0.0414(12) -0.0065(9) 0.0173(10) -0.0091(9) O6 0.0253(10) 0.0405(12) 0.0494(13) -0.0041(10) 0.0112(9) -0.0001(9) C28 0.0263(14) 0.0246(14) 0.0321(14) 0.0033(11) 0.0049(11) 0.0075(11) #================================================================== # 10. MOLECULAR GEOMETRY #=================================================================== loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag I1 C2 2.055(2) . . yes I2 C18 2.058(2) . . yes S1 C27 1.821(3) . . yes S1 O3 1.429(2) . . yes S1 O2 1.448(2) . . yes S1 O1 1.446(2) . . yes S2 O6 1.441(2) . . yes S2 O5 1.434(2) . . yes S2 O4 1.440(2) . . yes S2 C28 1.828(3) . . yes F1 C27 1.335(3) . . yes F2 C27 1.331(3) . . yes F3 C27 1.331(3) . . yes F4 C28 1.331(3) . . yes F5 C28 1.335(4) . . yes F6 C28 1.337(3) . . yes N1 C2 1.353(3) . . yes N1 C4 1.480(3) . . yes N1 N2 1.326(3) . . yes N2 N3 1.326(3) . . yes N3 C1 1.358(3) . . yes N3 C3 1.470(3) . . yes N4 N5 1.325(3) . . yes N4 C20 1.484(3) . . yes N4 C18 1.359(3) . . yes N5 N6 1.321(3) . . yes N6 C19 1.466(3) . . yes N6 C17 1.362(3) . . yes C1 C11 1.475(3) . . no C1 C2 1.381(3) . . no C4 C5 1.514(4) . . no C5 C10 1.388(4) . . no C5 C6 1.393(4) . . no C6 C7 1.389(4) . . no C7 C8 1.382(4) . . no C8 C9 1.385(4) . . no C9 C10 1.390(4) . . no C11 C12 1.402(4) . . no C11 C16 1.394(3) . . no C12 C13 1.389(4) . . no C13 C14 1.389(4) . . no C14 C15 1.390(4) . . no C15 C17 1.476(3) . . no C15 C16 1.396(3) . . no C17 C18 1.372(3) . . no C20 C21 1.506(4) . . no C21 C22 1.378(4) . . no C21 C26 1.383(4) . . no C22 C23 1.391(4) . . no C23 C24 1.380(5) . . no C24 C25 1.375(5) . . no C25 C26 1.390(4) . . no C3 H32 0.9800 . . no C3 H33 0.9800 . . no C3 H31 0.9800 . . no C4 H42 0.9900 . . no C4 H41 0.9900 . . no C6 H61 0.9500 . . no C7 H71 0.9500 . . no C8 H81 0.9500 . . no C9 H91 0.9500 . . no C10 H101 0.9500 . . no C12 H121 0.9500 . . no C13 H131 0.9500 . . no C14 H141 0.9500 . . no C16 H161 0.9500 . . no C19 H192 0.9800 . . no C19 H191 0.9800 . . no C19 H193 0.9800 . . no C20 H202 0.9900 . . no C20 H201 0.9900 . . no C22 H221 0.9500 . . no C23 H231 0.9500 . . no C24 H241 0.9500 . . no C25 H251 0.9500 . . no C26 H261 0.9500 . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 S1 C27 104.03(13) . . . yes O1 S1 O3 116.05(12) . . . yes O1 S1 C27 103.96(12) . . . yes O1 S1 O2 113.75(11) . . . yes O2 S1 C27 101.93(12) . . . yes O2 S1 O3 114.78(12) . . . yes O4 S2 C28 102.56(12) . . . yes O4 S2 O6 114.91(13) . . . yes O5 S2 O6 115.02(13) . . . yes O5 S2 C28 103.61(12) . . . yes O6 S2 C28 102.70(13) . . . yes O4 S2 O5 115.45(13) . . . yes C2 N1 C4 129.2(2) . . . yes N2 N1 C4 118.0(2) . . . yes N2 N1 C2 112.7(2) . . . yes N1 N2 N3 104.11(19) . . . yes N2 N3 C3 117.5(2) . . . yes C1 N3 C3 129.5(2) . . . yes N2 N3 C1 112.83(19) . . . yes N5 N4 C20 118.4(2) . . . yes C18 N4 C20 129.1(2) . . . yes N5 N4 C18 112.3(2) . . . yes N4 N5 N6 104.08(19) . . . yes C17 N6 C19 127.7(2) . . . yes N5 N6 C19 118.9(2) . . . yes N5 N6 C17 113.1(2) . . . yes C2 C1 C11 130.7(2) . . . no N3 C1 C11 124.4(2) . . . yes N3 C1 C2 104.87(19) . . . yes I1 C2 C1 130.21(17) . . . yes N1 C2 C1 105.5(2) . . . yes I1 C2 N1 124.14(17) . . . yes N1 C4 C5 111.7(2) . . . yes C6 C5 C10 119.2(2) . . . no C4 C5 C6 119.1(2) . . . no C4 C5 C10 121.7(2) . . . no C5 C6 C7 120.4(2) . . . no C6 C7 C8 119.9(3) . . . no C7 C8 C9 120.1(3) . . . no C8 C9 C10 120.0(2) . . . no C5 C10 C9 120.3(3) . . . no C1 C11 C12 119.7(2) . . . no C12 C11 C16 120.0(2) . . . no C1 C11 C16 120.3(2) . . . no C11 C12 C13 119.8(2) . . . no C12 C13 C14 120.5(2) . . . no C13 C14 C15 119.5(2) . . . no C14 C15 C17 120.3(2) . . . no C16 C15 C17 118.9(2) . . . no C14 C15 C16 120.8(2) . . . no C11 C16 C15 119.4(2) . . . no N6 C17 C18 104.6(2) . . . yes C15 C17 C18 130.8(2) . . . no N6 C17 C15 124.6(2) . . . yes N4 C18 C17 105.8(2) . . . yes I2 C18 N4 126.19(17) . . . yes I2 C18 C17 127.71(18) . . . yes N4 C20 C21 112.5(2) . . . yes C22 C21 C26 119.0(3) . . . no C20 C21 C22 120.8(3) . . . no C20 C21 C26 120.1(2) . . . no C21 C22 C23 120.4(3) . . . no C22 C23 C24 120.2(3) . . . no C23 C24 C25 119.7(3) . . . no C24 C25 C26 119.9(3) . . . no C21 C26 C25 120.7(3) . . . no N3 C3 H32 109.00 . . . no N3 C3 H31 110.00 . . . no H31 C3 H33 109.00 . . . no H31 C3 H32 109.00 . . . no H32 C3 H33 109.00 . . . no N3 C3 H33 109.00 . . . no N1 C4 H42 109.00 . . . no N1 C4 H41 109.00 . . . no H41 C4 H42 108.00 . . . no C5 C4 H42 109.00 . . . no C5 C4 H41 109.00 . . . no C7 C6 H61 120.00 . . . no C5 C6 H61 120.00 . . . no C8 C7 H71 120.00 . . . no C6 C7 H71 120.00 . . . no C7 C8 H81 120.00 . . . no C9 C8 H81 120.00 . . . no C10 C9 H91 120.00 . . . no C8 C9 H91 120.00 . . . no C9 C10 H101 120.00 . . . no C5 C10 H101 120.00 . . . no C13 C12 H121 120.00 . . . no C11 C12 H121 120.00 . . . no C14 C13 H131 120.00 . . . no C12 C13 H131 120.00 . . . no C13 C14 H141 120.00 . . . no C15 C14 H141 120.00 . . . no C15 C16 H161 120.00 . . . no C11 C16 H161 120.00 . . . no H191 C19 H192 110.00 . . . no H191 C19 H193 109.00 . . . no N6 C19 H191 109.00 . . . no N6 C19 H192 109.00 . . . no H192 C19 H193 109.00 . . . no N6 C19 H193 109.00 . . . no C21 C20 H202 109.00 . . . no C21 C20 H201 109.00 . . . no N4 C20 H201 109.00 . . . no N4 C20 H202 109.00 . . . no H201 C20 H202 108.00 . . . no C21 C22 H221 120.00 . . . no C23 C22 H221 120.00 . . . no C24 C23 H231 120.00 . . . no C22 C23 H231 120.00 . . . no C25 C24 H241 120.00 . . . no C23 C24 H241 120.00 . . . no C24 C25 H251 120.00 . . . no C26 C25 H251 120.00 . . . no C25 C26 H261 120.00 . . . no C21 C26 H261 120.00 . . . no F2 C27 F3 107.9(2) . . . yes S1 C27 F1 111.27(18) . . . yes S1 C27 F2 111.6(2) . . . yes S1 C27 F3 110.37(18) . . . yes F1 C27 F2 107.9(2) . . . yes F1 C27 F3 107.6(2) . . . yes S2 C28 F4 111.25(19) . . . yes S2 C28 F5 112.01(18) . . . yes S2 C28 F6 111.65(18) . . . yes F4 C28 F5 107.8(2) . . . yes F4 C28 F6 107.4(2) . . . yes F5 C28 F6 106.5(2) . . . yes _iucr_refine_instructions_details ; ; # End of Crystallographic Information File