# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 1999 # CCDC Number: 440/151 data_1 _publ_contact_author ' J. Elguero' _publ_contact_author_email 'iqmbe17@fresno.csic.es' _publ_requested_journal 'New Journal of Chemistry' _publ_authors_name ; Ibon Alkorta, Jose Elguero, Bruno Donnadieu, Joelle Jaffart, David Schagen and Hans-Heinrich Limbach ; #*********************************************************************** _audit_creation_method SHELXL-97 _chemical_formula_sum 'C20 H8 F24 N8' _chemical_formula_weight 816.34 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' 'F' 'F' 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.8547(9) _cell_length_b 10.1535(10) _cell_length_c 17.8903(19) _cell_angle_alpha 90.192(11) _cell_angle_beta 94.987(11) _cell_angle_gamma 106.811(11) _cell_volume 1533.2(3) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2)K _cell_measurement_reflns_used 5000 _cell_measurement_theta_min 3.6 _cell_measurement_theta_max 48.3 _exptl_crystal_description platelet _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.768 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 0.212 _exptl_absorpt_correction_type none _exptl_special_details ; The data were collected at low temperature (T=160K) on a STOE imaging plate diffraction system (I.P.D.S), equipped with an Oxford cryosystems cooler device, the crystal-to-detector distance was 80mm, 179 exposures were obtained with 0<(<250 and with the crystal rotated through 1.4 in (. Coverage of the unique set was over 94% complete to at least 24.1. Crystal decay was monitored by measuring 200 reflections by image. The final unit cell parameters were obtained by the least-squares refinement of 5000 reflections. Only satistical fluctuations were obsreved in the intensity monitors over the course of the data collection. Owing the low (x value, <0.1, no absorption correction was performed. ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; Stoe and Cie (1996) IPDS Manual. Version 2.75. Stoe and Cie, Darmstadt, Germany ; _diffrn_measurement_method ? _diffrn_reflns_number 11260 _diffrn_reflns_av_R_equivalents 0.0754 _diffrn_reflns_av_sigmaI/netI 0.0845 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 23.26 _reflns_number_total 4150 _reflns_number_gt 2332 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; Stoe and Cie (1996) IPDS Manual. Version 2.75. Stoe and Cie, Darmstadt, Germany ; _computing_cell_refinement ; Stoe and Cie (1996) IPDS Manual. Version 2.75. Stoe and Cie, Darmstadt, Germany ; _computing_data_reduction ; Stoe and Cie (1996) IPDS Manual. Version 2.75. Stoe and Cie, Darmstadt, Germany ; _computing_structure_solution ; Altomare, A., Cascarano, G., Giacovazzo G., Guagliardi A., Burla M.C., Polidori, G. & Camalli, M. (1994) SIR92 - a program for automatic solution of crystal structures by direct methods. J. Appl. Cryst. (27), 435 ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; Zsolnai,L.(1997). ZORTEP.Molecular Graphics Program.University of Heidelberg, Germany ; _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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 w=1/[\s^2^(Fo^2^)+(0.0919P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef 'not refined' _refine_ls_number_reflns 4150 _refine_ls_number_parameters 705 _refine_ls_number_restraints 3253 _refine_ls_R_factor_all 0.1119 _refine_ls_R_factor_gt 0.0573 _refine_ls_wR_factor_ref 0.1652 _refine_ls_wR_factor_gt 0.1373 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.170 _refine_ls_shift/su_max 0.137 _refine_ls_shift/su_mean 0.006 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1a N 0.8027(6) 0.1528(4) 0.6762(2) 0.0402(11) Uani 1 d DU . . N2a N 0.7980(5) 0.1558(4) 0.7508(2) 0.0388(11) Uani 1 d U . . C4a C 0.7407(7) -0.0657(5) 0.7114(3) 0.0424(13) Uani 1 d U . . H4a H 0.7143 -0.1633 0.7109 0.051 Uiso 1 calc R . . C5a C 0.7691(6) 0.0211(5) 0.6508(3) 0.0377(12) Uani 1 d DU . . C9a C 0.7669(7) -0.0108(5) 0.5696(3) 0.0522(13) Uani 1 d DU . . C3a C 0.7599(6) 0.0234(5) 0.7722(3) 0.0375(12) Uani 1 d DU . . C8a C 0.7444(8) -0.0080(5) 0.8519(3) 0.0530(14) Uani 1 d DU . . F10a F 0.8574(12) 0.0890(10) 0.8973(5) 0.077(3) Uani 0.572(11) d PDU A 1 F11a F 0.6082(10) 0.0031(13) 0.8768(4) 0.085(2) Uani 0.572(11) d PDU A 1 F12a F 0.7544(18) -0.1280(9) 0.8717(6) 0.091(3) Uani 0.572(11) d PDU A 1 F10'a F 0.771(2) 0.1000(12) 0.8955(7) 0.085(3) Uani 0.428(11) d PDU A 2 F11'a F 0.6036(14) -0.0957(17) 0.8616(6) 0.100(3) Uani 0.428(11) d PDU A 2 F12'a F 0.8508(17) -0.0761(15) 0.8745(7) 0.082(4) Uani 0.428(11) d PDU A 2 F13a F 0.787(4) 0.1030(17) 0.5295(12) 0.085(5) Uani 0.40(4) d PDU B 1 F14a F 0.622(2) -0.091(3) 0.5427(17) 0.077(5) Uani 0.40(4) d PDU B 1 F15a F 0.869(3) -0.077(3) 0.5540(18) 0.071(5) Uani 0.40(4) d PDU B 1 F13'a F 0.862(3) 0.0959(13) 0.5347(8) 0.079(4) Uani 0.60(4) d PDU B 2 F14'a F 0.6240(15) -0.044(2) 0.5339(11) 0.081(4) Uani 0.60(4) d PDU B 2 F15'a F 0.824(3) -0.1165(17) 0.5586(12) 0.074(4) Uani 0.60(4) d PDU B 2 H1A H 0.829(9) 0.244(6) 0.652(4) 0.110 Uiso 1 d D C 2 N1b N 1.2058(6) 0.2685(4) 0.8225(2) 0.0400(11) Uani 1 d DU . . N2b N 1.2111(5) 0.2699(4) 0.7476(2) 0.0368(10) Uani 1 d U . . C3b C 1.2666(7) 0.1645(5) 0.7288(3) 0.0398(12) Uani 1 d DU . . C4b C 1.2973(7) 0.0953(5) 0.7917(3) 0.0438(14) Uani 1 d U . . H4b H 1.3370 0.0179 0.7946 0.053 Uiso 1 calc R . . C5b C 1.2567(7) 0.1648(5) 0.8496(3) 0.0415(13) Uani 1 d DU . . C8b C 1.2857(8) 0.1374(6) 0.6490(3) 0.0572(14) Uani 1 d DU . . C9b C 1.2641(9) 0.1402(7) 0.9309(3) 0.0645(15) Uani 1 d DU . . F10b F 1.2798(17) 0.2399(8) 0.6051(4) 0.096(3) Uani 0.780(16) d PDU D 1 F11b F 1.4295(7) 0.1153(10) 0.6428(4) 0.076(2) Uani 0.780(16) d PDU D 1 F12b F 1.1772(10) 0.0220(7) 0.6212(5) 0.077(2) Uani 0.780(16) d PDU D 1 F10'b F 1.182(4) 0.191(3) 0.6058(11) 0.084(5) Uani 0.220(16) d PDU D 2 F11'b F 1.427(2) 0.188(4) 0.6289(13) 0.096(4) Uani 0.220(16) d PDU D 2 F12'b F 1.232(4) 0.0038(16) 0.6295(18) 0.077(5) Uani 0.220(16) d PDU D 2 F13b F 1.278(4) 0.253(2) 0.9732(10) 0.098(4) Uani 0.32(2) d PDU E 1 F14b F 1.399(2) 0.107(3) 0.9526(14) 0.091(4) Uani 0.32(2) d PDU E 1 F15b F 1.149(3) 0.035(2) 0.951(2) 0.099(6) Uani 0.32(2) d PDU E 1 F13'b F 1.181(2) 0.2071(14) 0.9671(5) 0.092(3) Uani 0.68(2) d PDU E 2 F14'b F 1.4068(12) 0.1669(19) 0.9638(7) 0.110(3) Uani 0.68(2) d PDU E 2 F15'b F 1.1899(18) 0.0057(10) 0.9452(9) 0.100(3) Uani 0.68(2) d PU E 2 H1b H 1.167(11) 0.336(8) 0.851(5) 0.151 Uiso 1 d D F 2 N1c N 0.9013(6) 0.4193(4) 0.8331(2) 0.0392(11) Uani 1 d DU . . N2c N 1.0502(5) 0.4557(4) 0.8668(2) 0.0406(11) Uani 1 d U . . C3c C 1.0759(6) 0.5789(5) 0.9017(3) 0.0433(12) Uani 1 d DU . . C4c C 0.9401(7) 0.6232(5) 0.8906(3) 0.0476(14) Uani 1 d U . . H4c H 0.9249 0.7059 0.9089 0.057 Uiso 1 calc R . . C5c C 0.8323(6) 0.5181(5) 0.8464(3) 0.0423(12) Uani 1 d DU . . C8c C 1.2330(7) 0.6487(6) 0.9433(3) 0.0522(13) Uani 1 d DU . . C9c C 0.6681(8) 0.5051(6) 0.8161(4) 0.0622(15) Uani 1 d DU . . F10c F 1.3164(11) 0.5589(9) 0.9589(8) 0.088(3) Uani 0.75(2) d PDU G 1 F11c F 1.3228(13) 0.7523(12) 0.9077(5) 0.087(3) Uani 0.75(2) d PDU G 1 F12c F 1.2154(14) 0.6980(11) 1.0101(4) 0.067(2) Uani 0.75(2) d PDU G 1 F10'c F 1.350(2) 0.604(3) 0.9219(17) 0.080(4) Uani 0.25(2) d PDU G 2 F11'c F 1.277(3) 0.7847(17) 0.9221(18) 0.075(5) Uani 0.25(2) d PDU G 2 F12'c F 1.230(4) 0.656(4) 1.0158(8) 0.075(5) Uani 0.25(2) d PDU G 2 F13C F 0.5930(12) 0.3806(8) 0.7901(8) 0.102(3) Uani 0.593(8) d PDU H 1 F14C F 0.6755(10) 0.5898(9) 0.7560(5) 0.089(2) Uani 0.593(8) d PDU H 1 F15C F 0.5863(10) 0.5484(13) 0.8627(5) 0.100(3) Uani 0.593(8) d PDU H 1 F13'c F 0.6239(19) 0.4264(15) 0.7528(7) 0.093(3) Uani 0.407(8) d PDU H 2 F14'c F 0.6391(16) 0.6229(11) 0.8050(10) 0.100(3) Uani 0.407(8) d PDU H 2 F15'c F 0.5578(12) 0.4381(16) 0.8624(7) 0.097(3) Uani 0.407(8) d PDU H 2 H1c H 0.862(11) 0.329(6) 0.803(5) 0.146 Uiso 1 d D I 2 N1d N 1.0868(6) 0.4716(4) 0.6646(2) 0.0411(11) Uani 1 d DU . . N2d N 0.9387(6) 0.4223(4) 0.6310(2) 0.0420(11) Uani 1 d U . . C3d C 0.9005(7) 0.5285(5) 0.5969(3) 0.0446(13) Uani 1 d DU . . C4d C 1.0291(7) 0.6487(6) 0.6082(3) 0.0490(15) Uani 1 d U . . H4d H 1.0359 0.7380 0.5902 0.059 Uiso 1 calc R . . C5d C 1.1431(7) 0.6076(5) 0.6515(3) 0.0458(13) Uani 1 d DU . . C8d C 0.7426(8) 0.5057(6) 0.5553(3) 0.0591(14) Uani 1 d DU . . C9d C 1.3065(8) 0.6899(6) 0.6811(4) 0.0634(15) Uani 1 d DU . . F10d F 0.635(2) 0.3905(18) 0.5725(13) 0.093(4) Uani 0.41(2) d PDU J 1 F11d F 0.680(2) 0.6082(18) 0.5789(12) 0.076(4) Uani 0.41(2) d PDU J 1 F12d F 0.741(4) 0.520(3) 0.4827(8) 0.077(4) Uani 0.41(2) d PDU J 1 F10'd F 0.6744(15) 0.3690(8) 0.5363(9) 0.084(3) Uani 0.59(2) d PDU J 2 F11'd F 0.6402(16) 0.5484(18) 0.5890(8) 0.087(3) Uani 0.59(2) d PDU J 2 F12'd F 0.761(2) 0.5663(16) 0.4888(6) 0.073(3) Uani 0.59(2) d PDU J 2 F13D F 1.3448(12) 0.6312(12) 0.7520(6) 0.092(3) Uani 0.438(7) d PU K 1 F14D F 1.4218(14) 0.6783(15) 0.6476(7) 0.092(3) Uani 0.438(7) d PU K 1 F15D F 1.3256(17) 0.8126(12) 0.7022(10) 0.100(3) Uani 0.438(7) d PU K 1 F13'd F 1.4034(11) 0.6156(9) 0.6874(7) 0.100(3) Uani 0.562(7) d PDU K 2 F14'd F 1.3713(9) 0.7854(9) 0.6291(5) 0.097(3) Uani 0.562(7) d PDU K 2 F15'd F 1.3052(14) 0.7612(12) 0.7407(5) 0.105(3) Uani 0.562(7) d PDU K 2 H1d H 1.140(12) 0.407(9) 0.691(5) 0.158 Uiso 1 d 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 N1a 0.046(3) 0.033(2) 0.040(2) 0.0037(17) 0.006(2) 0.009(2) N2a 0.042(3) 0.035(2) 0.038(2) 0.0022(17) 0.004(2) 0.008(2) C4a 0.045(4) 0.030(2) 0.048(3) 0.002(2) 0.004(3) 0.005(2) C5a 0.035(4) 0.036(3) 0.041(2) 0.0009(18) 0.004(2) 0.008(2) C9a 0.060(4) 0.052(3) 0.045(3) 0.000(2) 0.001(3) 0.017(3) C3a 0.036(4) 0.034(2) 0.040(2) 0.0041(18) 0.004(2) 0.008(2) C8a 0.066(4) 0.044(3) 0.049(3) 0.008(2) 0.010(3) 0.014(3) F10a 0.077(6) 0.104(5) 0.038(3) -0.002(3) 0.005(4) 0.010(4) F11a 0.075(5) 0.129(7) 0.063(4) 0.033(5) 0.031(3) 0.043(4) F12a 0.153(8) 0.075(4) 0.067(4) 0.035(4) 0.042(7) 0.057(5) F10'a 0.129(9) 0.081(5) 0.052(4) -0.002(4) 0.032(7) 0.034(5) F11'a 0.092(6) 0.123(7) 0.070(6) 0.038(6) 0.035(5) -0.004(5) F12'a 0.115(8) 0.097(8) 0.054(5) 0.037(6) 0.018(7) 0.057(7) F13a 0.145(13) 0.068(5) 0.045(5) 0.012(4) 0.028(10) 0.032(7) F14a 0.064(5) 0.104(11) 0.052(8) -0.012(8) -0.015(5) 0.015(6) F15a 0.072(9) 0.088(10) 0.057(6) -0.014(9) 0.013(7) 0.032(9) F13'a 0.117(9) 0.071(4) 0.045(4) 0.002(3) 0.039(6) 0.014(5) F14'a 0.067(4) 0.132(11) 0.047(5) -0.008(7) -0.010(4) 0.038(5) F15'a 0.094(10) 0.074(6) 0.062(5) -0.017(6) 0.000(7) 0.042(7) N1b 0.043(3) 0.045(3) 0.035(2) -0.0009(18) 0.003(2) 0.018(2) N2B 0.038(3) 0.035(2) 0.037(2) -0.0004(17) 0.0026(19) 0.010(2) C3b 0.047(4) 0.032(3) 0.040(2) 0.0000(19) 0.004(2) 0.013(2) C4b 0.055(4) 0.041(3) 0.042(3) 0.005(2) 0.006(3) 0.025(3) C5b 0.045(4) 0.044(3) 0.038(2) 0.000(2) 0.004(2) 0.018(3) C8b 0.081(4) 0.053(3) 0.045(3) 0.001(2) 0.008(3) 0.032(3) C9b 0.084(4) 0.077(4) 0.042(3) 0.005(3) 0.003(3) 0.039(3) F10b 0.172(8) 0.092(4) 0.051(3) 0.027(3) 0.042(4) 0.070(5) F11b 0.078(3) 0.100(5) 0.062(3) -0.004(3) 0.024(3) 0.041(3) F12b 0.085(5) 0.088(3) 0.055(3) -0.027(3) -0.009(3) 0.027(3) F10'b 0.148(10) 0.101(10) 0.032(6) 0.024(8) 0.026(9) 0.077(9) F11'b 0.114(6) 0.115(9) 0.061(7) 0.014(8) 0.044(6) 0.028(7) F12'b 0.110(12) 0.067(5) 0.062(9) -0.023(6) -0.006(10) 0.041(6) F13b 0.143(9) 0.125(7) 0.042(5) -0.016(5) 0.007(8) 0.066(7) F14b 0.105(7) 0.143(12) 0.041(8) 0.000(9) -0.014(6) 0.070(7) F15b 0.118(8) 0.118(8) 0.069(8) 0.044(8) 0.028(8) 0.041(8) F13'b 0.136(8) 0.132(6) 0.041(3) 0.009(4) 0.026(5) 0.085(7) F14'b 0.094(4) 0.187(9) 0.047(4) -0.008(6) -0.017(3) 0.045(5) F15'b 0.158(8) 0.086(4) 0.063(4) 0.029(4) 0.019(5) 0.040(4) N1c 0.044(3) 0.031(2) 0.043(3) 0.0024(17) 0.006(2) 0.011(2) N2c 0.043(3) 0.041(2) 0.041(2) -0.0058(18) 0.005(2) 0.017(2) C3c 0.040(3) 0.044(3) 0.045(3) -0.005(2) 0.010(2) 0.011(2) C4c 0.051(4) 0.033(3) 0.064(4) -0.006(2) 0.005(3) 0.019(3) C5c 0.043(3) 0.036(3) 0.048(3) 0.000(2) 0.004(2) 0.013(2) C8c 0.044(4) 0.055(3) 0.055(3) -0.011(2) 0.008(3) 0.010(3) C9c 0.055(4) 0.054(3) 0.078(4) 0.002(3) -0.005(3) 0.020(3) F10c 0.054(4) 0.092(4) 0.119(7) -0.029(4) -0.022(4) 0.032(4) F11c 0.052(5) 0.110(5) 0.072(4) 0.001(4) 0.013(3) -0.023(4) F12c 0.063(4) 0.078(6) 0.051(3) -0.017(3) 0.002(3) 0.011(4) F10'c 0.040(5) 0.103(8) 0.094(9) -0.032(7) 0.002(6) 0.017(6) F11'c 0.049(11) 0.069(6) 0.089(10) 0.006(7) 0.013(8) -0.012(5) F12'c 0.065(9) 0.097(13) 0.049(4) -0.006(6) 0.003(5) 0.003(10) F13c 0.051(5) 0.073(4) 0.168(8) -0.018(4) -0.025(6) 0.006(4) F14c 0.070(5) 0.104(5) 0.094(5) 0.027(4) -0.015(4) 0.032(4) F15c 0.053(5) 0.142(7) 0.117(5) -0.009(5) 0.011(4) 0.045(5) F13'c 0.062(6) 0.107(7) 0.097(6) -0.017(5) -0.028(5) 0.016(6) F14'c 0.075(6) 0.089(5) 0.144(9) 0.007(5) -0.019(7) 0.045(5) F15'c 0.037(4) 0.125(7) 0.121(6) 0.010(6) 0.000(4) 0.010(6) N1d 0.045(3) 0.037(2) 0.045(3) 0.0037(19) 0.005(2) 0.016(2) N2d 0.043(3) 0.041(2) 0.042(3) 0.0098(19) 0.007(2) 0.013(2) C3d 0.042(3) 0.046(3) 0.047(3) 0.013(2) 0.011(2) 0.013(2) C4d 0.048(4) 0.038(3) 0.061(4) 0.014(3) 0.007(3) 0.013(2) C5d 0.047(3) 0.037(3) 0.054(3) 0.000(2) 0.005(2) 0.014(2) C8d 0.051(4) 0.056(3) 0.068(3) 0.018(3) 0.003(3) 0.013(3) C9d 0.054(4) 0.045(3) 0.090(4) -0.003(3) -0.006(3) 0.017(3) F10d 0.053(6) 0.086(5) 0.119(9) 0.037(6) -0.011(6) -0.010(5) F11d 0.028(8) 0.094(7) 0.106(8) -0.008(8) 0.012(6) 0.018(7) F12d 0.064(8) 0.103(13) 0.060(4) 0.000(5) -0.005(4) 0.023(9) F10'd 0.056(6) 0.069(3) 0.111(9) 0.010(4) -0.018(5) -0.001(3) F11'd 0.041(5) 0.124(7) 0.093(5) 0.004(6) 0.009(4) 0.021(6) F12'd 0.075(7) 0.080(8) 0.059(4) 0.018(4) -0.009(4) 0.019(6) F13d 0.059(6) 0.113(6) 0.087(5) 0.010(5) -0.024(4) 0.008(5) F14d 0.050(4) 0.108(7) 0.104(7) -0.024(5) 0.006(5) -0.001(5) F15d 0.080(6) 0.060(4) 0.147(9) -0.034(5) -0.029(7) 0.013(5) F13'd 0.064(5) 0.087(5) 0.148(8) -0.002(5) -0.034(6) 0.033(4) F14'd 0.061(5) 0.089(5) 0.114(5) 0.027(4) -0.010(4) -0.019(4) F15'd 0.091(6) 0.104(7) 0.092(6) -0.040(4) -0.006(5) -0.013(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 N1a N2a 1.338(6) . ? N1a C5a 1.351(6) . ? N2a C3a 1.353(6) . ? C4a C3a 1.381(7) . ? C4a C5a 1.393(7) . ? C5a C9a 1.484(7) . ? C9a F15a 1.315(14) . ? C9a F14'a 1.317(11) . ? C9a F15'a 1.333(10) . ? C9a F13a 1.338(12) . ? C9a F14a 1.354(13) . ? C9a F13'a 1.358(10) . ? C3a C8a 1.470(7) . ? C8a F10'a 1.295(11) . ? C8a F12a 1.296(8) . ? C8a F11'a 1.332(10) . ? C8a F11a 1.356(8) . ? C8a F12'a 1.358(10) . ? C8a F10a 1.383(9) . ? N1b C5b 1.337(6) . ? N1b N2b 1.344(6) . ? N2b C3b 1.353(6) . ? C3b C4b 1.378(7) . ? C3b C8b 1.485(7) . ? C4b C5b 1.380(7) . ? C5b C9b 1.475(7) . ? C8b F11'b 1.292(14) . ? C8b F10b 1.316(7) . ? C8b F12'b 1.335(14) . ? C8b F12b 1.343(8) . ? C8b F11b 1.369(8) . ? C8b F10'b 1.380(14) . ? C9b F14'b 1.299(10) . ? C9b F15b 1.325(15) . ? C9b F13b 1.337(13) . ? C9b F13'b 1.337(9) . ? C9b F14b 1.357(14) . ? C9b F15'b 1.370(12) . ? N1c C5c 1.348(6) . ? N1c N2c 1.349(6) . ? N2c C3c 1.347(6) . ? C3c C4c 1.399(7) . ? C3c C8c 1.495(7) . ? C4c C5c 1.396(8) . ? C5c C9c 1.475(8) . ? C8c F12'c 1.302(14) . ? C8c F11c 1.324(8) . ? C8c F10'c 1.331(13) . ? C8c F12c 1.334(8) . ? C8c F10c 1.345(8) . ? C8c F11'c 1.385(14) . ? C9c F15c 1.305(9) . ? C9c F14'c 1.306(10) . ? C9c F13c 1.308(9) . ? C9C F13'c 1.345(11) . ? C9C F15'c 1.364(11) . ? C9C F14c 1.374(8) . ? N1d N2d 1.347(6) . ? N1d C5d 1.355(7) . ? N2d C3d 1.352(6) . ? C3d C4d 1.408(8) . ? C3d C8d 1.481(8) . ? C4d C5d 1.378(7) . ? C5d C9d 1.496(8) . ? C8d F11'd 1.302(11) . ? C8d F12d 1.307(13) . ? C8d F10d 1.332(11) . ? C8d F12'd 1.342(10) . ? C8d F10'd 1.372(9) . ? C8d F11 1.391(12) . ? C9d F15d 1.260(13) . ? C9d F14d 1.261(13) . ? C9d F15'd 1.290(10) . ? C9d F13'd 1.294(9) . ? C9d F14'd 1.383(9) . ? C9d F13d 1.457(11) . ? 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 N2a N1a C5a 109.7(4) . . ? N1a N2a C3a 106.6(4) . . ? C3a C4a C5a 103.7(4) . . ? N1a C5a C4a 108.8(4) . . ? N1a C5a C9a 120.5(4) . . ? C4a C5a C9a 130.6(5) . . ? F14'a C9a F15'a 106.4(10) . . ? F15a C9a F13a 110.6(14) . . ? F15a C9a F14a 106.8(14) . . ? F13a C9a F14a 103.4(12) . . ? F14'a C9a F13'a 108.7(9) . . ? F15'a C9a F13'a 104.9(9) . . ? F15a C9a C5a 114.0(15) . . ? F14'a C9a C5a 113.4(11) . . ? F15'a C9a C5a 111.5(10) . . ? F13a C9a C5a 111.1(11) . . ? F14a C9a C5a 110.2(14) . . ? F13'a C9a C5a 111.4(8) . . ? N2a C3a C4a 111.1(4) . . ? N2a C3a C8a 119.9(4) . . ? C4a C3a C8a 129.1(4) . . ? F10'a C8a F11'a 110.4(10) . . ? F12a C8a F11a 105.8(7) . . ? F10'a C8a F12'a 107.9(9) . . ? F11'a C8a F12'a 104.8(8) . . ? F12a C8a F10a 107.2(8) . . ? F11a C8a F10a 101.6(7) . . ? F10'a C8a C3a 113.9(8) . . ? F12a C8a C3a 116.2(7) . . ? F11'a C8a C3a 111.4(6) . . ? F11a C8a C3a 114.1(5) . . ? F12'a C8a C3a 108.1(7) . . ? F10a C8a C3a 110.7(6) . . ? C5b N1b N2b 109.0(4) . . ? N1b N2b C3b 106.8(4) . . ? N2b C3b C4b 110.5(4) . . ? N2b C3b C8b 120.2(4) . . ? C4b C3b C8b 129.4(5) . . ? C3b C4b C5b 103.9(4) . . ? N1b C5b C4b 109.8(4) . . ? N1b C5b C9b 120.4(5) . . ? C4b C5b C9b 129.8(5) . . ? F11'b C8b F12'b 109.7(16) . . ? F10b C8b F12b 109.0(6) . . ? F10b C8b F11b 106.5(6) . . ? F12b C8b F11b 105.5(5) . . ? F11'b C8b F10'b 109.5(13) . . ? F12'b C8b F10'b 101.8(14) . . ? F11'b C8b C3b 115.4(12) . . ? F10b C8b C3b 113.5(5) . . ? F12'b C8b C3b 112.5(15) . . ? F12b C8b C3b 111.5(7) . . ? F11b C8b C3b 110.3(5) . . ? F10'b C8b C3b 107.0(11) . . ? F15b C9b F13b 111.0(15) . . ? F14'b C9b F13'b 109.8(7) . . ? F15b C9b F14b 104.2(15) . . ? F13b C9b F14b 103.0(12) . . ? F14'b C9b F15'b 106.0(9) . . ? F13'b C9b F15'b 102.1(8) . . ? F14'b C9b C5b 114.5(9) . . ? F15b C9b C5b 114.5(17) . . ? F13b C9b C5b 113.5(10) . . ? F13'b C9b C5b 112.2(6) . . ? F14b C9b C5b 109.6(12) . . ? F15'b C9b C5b 111.4(8) . . ? C5c N1c N2c 109.5(4) . . ? C3c N2c N1c 107.7(4) . . ? N2c C3c C4c 109.8(5) . . ? N2c C3c C8c 120.5(5) . . ? C4c C3c C8c 129.7(5) . . ? C5c C4c C3c 104.3(4) . . ? N1c C5c C4c 108.8(5) . . ? N1c C5c C9c 121.1(5) . . ? C4c C5c C9c 130.1(5) . . ? F12'c C8c F10'c 113.7(16) . . ? F11c C8c F12c 107.2(7) . . ? F11c C8c F10c 107.9(7) . . ? F12c C8c F10c 104.7(6) . . ? F12'c C8c F11'c 104.4(15) . . ? F10'c C8c F11'c 102.5(13) . . ? F12'c C8c C3c 114.2(17) . . ? F11c C8c C3c 114.4(6) . . ? F10'c C8c C3c 113.3(10) . . ? F12c C8c C3c 111.1(7) . . ? F10c C8c C3c 111.1(5) . . ? F11'c C8c C3c 107.4(12) . . ? F15c C9c F13c 111.3(8) . . ? F14c' C9c F13'c 109.3(9) . . ? F14'c C9c F15'c 104.4(10) . . ? F13'c C9c F15'c 102.1(9) . . ? F15c C9c F14c 105.1(7) . . ? F13c C9c F14c 106.3(8) . . ? F15c C9c C5c 113.6(6) . . ? F14'c C9c C5c 113.9(7) . . ? F13c C9c C5c 112.4(6) . . ? F13'c C9c C5c 113.0(8) . . ? F15'c C9c C5c 113.2(6) . . ? F14c C9c C5c 107.4(6) . . ? N2d N1d C5d 109.4(4) . . ? N1d N2d C3d 107.4(4) . . ? N2d C3d C4d 109.6(4) . . ? N2d C3d C8d 119.9(5) . . ? C4d C3d C8d 130.5(5) . . ? C5d C4d C3d 104.3(4) . . ? N1d C5d C4d 109.2(5) . . ? N1d C5d C9d 121.4(5) . . ? C4d C5d C9d 129.4(5) . . ? F12d C8d F10d 111.3(12) . . ? F11'd C8d F12'd 108.5(10) . . ? F11'd C8d F10'd 107.6(8) . . ? F12'd C8d F10'd 103.7(8) . . ? F12d C8d F11d 103.3(13) . . ? F10d C8d F11d 102.9(10) . . ? F11'd C8d C3d 116.2(8) . . ? F12d C8d C3d 116.2(15) . . ? F10d C8d C3d 114.1(8) . . ? F12'd C8d C3d 109.0(10) . . ? F10'd C8d C3d 111.1(6) . . ? F11d C8d C3d 107.4(9) . . ? F15d C9d F14d 111.6(11) . . ? F15'd C9d F13'd 114.6(9) . . ? F15'd C9d F14'd 105.2(7) . . ? F13'd C9d F14'd 102.9(9) . . ? F15d C9d F13d 100.5(10) . . ? F14d C9d F13d 97.9(9) . . ? F15d C9d C5d 117.3(8) . . ? F14d C9d C5d 118.3(8) . . ? F15'd C9d C5d 111.7(7) . . ? F13'd C9d C5d 112.1(6) . . ? F14'd C9d C5d 109.6(6) . . ? F13d C9d C5d 107.5(6) . . ? 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 N1a C5a C9a F13a -5.7(18) . . . . ? N1a C5a C9a F14a -119.7(15) . . . . ? N1a C5a C9a F15a 120.1(16) . . . . ? N1a C5a C9a F13'a 26.3(13) . . . . ? N1a C5a C9a F14'a -96.8(13) . . . . ? N1a C5a C9a F15'a 143.2(12) . . . . ? N2a C3a C8a F10a -37.8(9) . . . . ? N2a C3a C8a F11a 76.1(9) . . . . ? N2a C3a C8a F12a -160.4(9) . . . . ? N2a C3a C8a F10'a -0.6(12) . . . . ? N2a C3a C8a F11'a 125.0(10) . . . . ? N2a C3a C8a F12'a -120.4(9) . . . . ? N1b C5b C9b F13b -25.0(18) . . . . ? N1b C5b C9b F14b -139.5(14) . . . . ? N1b C5b C9b F15b 103.8(16) . . . . ? N1b C5b C9b F13'b 15.3(12) . . . . ? N1b C5b C9b F14'b -110.7(11) . . . . ? N1b C5b C9b F15'b 129.1(9) . . . . ? N2b C3b C8b F10b 14.7(10) . . . . ? N2b C3b C8b F11b 134.2(6) . . . . ? N2b C3b C8b F12b -108.9(7) . . . . ? N2b C3b C8b F10'b -24.6(17) . . . . ? N2b C3b C8b F11'b 98(2) . . . . ? N2b C3b C8b F12'b -135.6(16) . . . . ? N1c C5c C9c F13c 12.9(11) . . . . ? N1c C5c C9c F14c -103.7(7) . . . . ? N1c C5c C9c F15c 140.5(8) . . . . ? N1c C5c C9c F13'c -26.9(11) . . . . ? N1c C5c C9c F14'c -152.4(11) . . . . ? N1c C5c C9c F15'c 88.5(10) . . . . ? N2c C3c C8c F10c -18.4(10) . . . . ? N2c C3c C8c F11c 104.0(9) . . . . ? N2c C3c C8c F12c -134.5(7) . . . . ? N2c C3c C8c F10'c 20.8(19) . . . . ? N2c C3c C8c F11'c 133.2(16) . . . . ? N2c C3c C8c F12'c -111.6(18) . . . . ? N1d C5d C9d F13d -31.9(9) . . . . ? N1d C5d C9d F14d 77.6(11) . . . . ? N1d C5d C9d F15d -144.0(11) . . . . ? N1d C5d C9d F13'd 29.6(11) . . . . ? N1d C5d C9d F14'd 143.1(7) . . . . ? N1d C5d C9d F15'd -100.6(9) . . . . ? N2d C3d C8d F10d 17.9(16) . . . . ? N2d C3d C8d F11d 131.3(11) . . . . ? N2d C3d C8d F12d -113.6(14) . . . . ? N2d C3d C8d F10'd -20.2(11) . . . . ? N2d C3d C8d F11'd 103.2(10) . . . . ? N2d C3d C8d F12'd -133.9(10) . . . . ? 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 N1A H1A N2D 1.00(5) 1.84(5) 2.806(6) 160(7) . N1D H1D N2B 1.01(5) 1.94(5) 2.941(5) 172(9) . N1B H1B N2C 1.01(5) 1.84(6) 2.799(6) 157(8) . N1C H1C N2A 1.01(5) 1.90(5) 2.913(6) 176(8) . _diffrn_measured_fraction_theta_max 0.943 _diffrn_reflns_theta_full 23.26 _diffrn_measured_fraction_theta_full 0.943 _refine_diff_density_max 0.337 _refine_diff_density_min -0.264 _refine_diff_density_rms 0.053