# 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_jm055 _database_code_depnum_ccdc_archive 'CCDC 866318' #TrackingRef 'JM055.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H11 N2 O2 F8 I2 1+, 2.5(C4 H8 O2), I 1-' _chemical_formula_sum 'C34 H31 F8 I3 N2 O7' _chemical_formula_weight 1112.31 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.3334(16) _cell_length_b 11.853(2) _cell_length_c 18.412(3) _cell_angle_alpha 96.076(12) _cell_angle_beta 96.664(12) _cell_angle_gamma 99.784(13) _cell_volume 1977.2(6) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 6663 _cell_measurement_theta_min 4.408 _cell_measurement_theta_max 51.182 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.868 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1072 _exptl_absorpt_coefficient_mu 2.456 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.' _exptl_absorpt_correction_T_min 0.3789 _exptl_absorpt_correction_T_max 0.4619 _exptl_special_details ; Bruker KRYOFLEX low temperature device. ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_standards_decay_% 0.00 _diffrn_reflns_number 20329 _diffrn_reflns_av_R_equivalents 0.0362 _diffrn_reflns_av_sigmaI/netI 0.0586 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.25 _diffrn_reflns_theta_max 26.00 _reflns_number_total 7669 _reflns_number_gt 5278 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution ; SIR2002 (Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103.) ; _computing_structure_refinement 'SHELXL (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122)' _computing_molecular_graphics ; ORTEP-3 (Farrugia, L.J. (1997) Jour. Appl. Cryst. 30, 565) Mercury (Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457 ; _computing_publication_material SHELXTL _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. Only the H atoms between N1 and N2(x,1+y,z) was refined. The dioxane molecules have very high ADPs and SHELXL-97 suggests to split at list three atoms. Notwithstanding, no attempt to refine these molecules as disordered was judged necessary. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0320P)^2^+8.2046P] 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 ? _refine_ls_number_reflns 7669 _refine_ls_number_parameters 490 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0833 _refine_ls_R_factor_gt 0.0453 _refine_ls_wR_factor_ref 0.1089 _refine_ls_wR_factor_gt 0.0929 _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_restrained_S_all 1.076 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I1 I 0.10341(5) 0.39824(4) 1.06104(2) 0.03346(13) Uani 1 1 d . . . I2 I 0.88137(6) 0.49397(6) 0.38506(3) 0.06018(19) Uani 1 1 d . . . F1 F 0.1755(5) 0.3526(3) 0.7728(2) 0.0463(10) Uani 1 1 d . . . F2 F 0.0495(4) 0.2914(3) 0.8886(2) 0.0495(11) Uani 1 1 d . . . F3 F 0.3680(5) 0.5999(3) 1.0416(2) 0.0474(11) Uani 1 1 d . . . F4 F 0.4889(5) 0.6643(3) 0.9261(2) 0.0481(11) Uani 1 1 d . . . F5 F 0.5168(5) 0.3296(3) 0.5666(2) 0.0575(12) Uani 1 1 d . . . F6 F 0.6677(6) 0.3150(4) 0.4538(3) 0.0674(14) Uani 1 1 d . . . F7 F 0.8699(6) 0.7112(4) 0.5085(3) 0.0745(15) Uani 1 1 d . . . F8 F 0.7230(5) 0.7244(3) 0.6248(2) 0.0575(12) Uani 1 1 d . . . O1 O 0.3950(5) 0.5327(3) 0.7830(2) 0.0280(10) Uani 1 1 d . . . O2 O 0.5372(5) 0.5354(3) 0.6561(2) 0.0283(10) Uani 1 1 d . . . N1 N 0.5782(7) 0.9415(5) 0.7619(4) 0.0523(18) Uani 1 1 d D . . H1N H 0.585(9) 1.0522(15) 0.753(5) 0.078 Uiso 1 1 d D . . N2 N 0.5947(8) 0.1659(5) 0.7544(5) 0.069(2) Uani 1 1 d . . . C1 C 0.2269(7) 0.4126(5) 0.8396(3) 0.0286(14) Uani 1 1 d . . . C2 C 0.1614(7) 0.3816(5) 0.8988(4) 0.0311(15) Uani 1 1 d . . . C3 C 0.2069(7) 0.4417(6) 0.9695(4) 0.0308(15) Uani 1 1 d . . . C4 C 0.3187(7) 0.5359(6) 0.9757(3) 0.0316(15) Uani 1 1 d . . . C5 C 0.3840(7) 0.5683(5) 0.9158(4) 0.0312(15) Uani 1 1 d . . . C6 C 0.3405(7) 0.5063(5) 0.8458(3) 0.0258(14) Uani 1 1 d . . . C7 C 0.5466(8) 0.5827(7) 0.7864(4) 0.0469(19) Uani 1 1 d . . . H7 H 0.6003 0.5769 0.8358 0.056 Uiso 1 1 calc R . . C8 C 0.5592(8) 0.7145(6) 0.7743(4) 0.0439(19) Uani 1 1 d . . . C9 C 0.6741(8) 0.7924(5) 0.8121(4) 0.0428(19) Uani 1 1 d . . . H9 H 0.7504 0.7676 0.8415 0.051 Uiso 1 1 calc R . . C10 C 0.6780(9) 0.9072(6) 0.8071(5) 0.055(2) Uani 1 1 d . . . H10 H 0.7534 0.9630 0.8364 0.067 Uiso 1 1 calc R . . C11 C 0.4700(9) 0.8671(6) 0.7218(5) 0.050(2) Uani 1 1 d . . . H11 H 0.4020 0.8939 0.6883 0.061 Uiso 1 1 calc R . . C12 C 0.4538(9) 0.7503(6) 0.7277(5) 0.050(2) Uani 1 1 d . . . H12 H 0.3731 0.6967 0.7006 0.061 Uiso 1 1 calc R . . C13 C 0.6131(8) 0.5238(6) 0.7280(4) 0.0413(18) Uani 1 1 d . . . H13 H 0.7191 0.5598 0.7316 0.050 Uiso 1 1 calc R . . C14 C 0.5998(8) 0.3953(5) 0.7403(4) 0.0430(19) Uani 1 1 d . . . C15 C 0.4723(8) 0.3150(5) 0.7195(4) 0.0392(18) Uani 1 1 d . . . H15 H 0.3844 0.3385 0.7007 0.047 Uiso 1 1 calc R . . C16 C 0.4737(9) 0.2014(6) 0.7260(5) 0.053(2) Uani 1 1 d . . . H16 H 0.3865 0.1460 0.7099 0.064 Uiso 1 1 calc R . . C17 C 0.7144(10) 0.2432(6) 0.7770(5) 0.064(3) Uani 1 1 d . . . H17 H 0.7994 0.2179 0.7980 0.077 Uiso 1 1 calc R . . C18 C 0.7226(9) 0.3580(6) 0.7718(5) 0.056(2) Uani 1 1 d . . . H18 H 0.8110 0.4114 0.7894 0.067 Uiso 1 1 calc R . . C19 C 0.6194(7) 0.5272(5) 0.6005(3) 0.0292(15) Uani 1 1 d . . . C20 C 0.6087(8) 0.4237(6) 0.5541(4) 0.0356(16) Uani 1 1 d . . . C21 C 0.6848(8) 0.4183(6) 0.4952(4) 0.0409(18) Uani 1 1 d . . . C22 C 0.7752(7) 0.5139(7) 0.4786(4) 0.0391(18) Uani 1 1 d . . . C23 C 0.7855(8) 0.6148(7) 0.5225(4) 0.0434(18) Uani 1 1 d . . . C24 C 0.7102(8) 0.6220(6) 0.5824(4) 0.0389(17) Uani 1 1 d . . . O3 O 0.8876(9) 1.0340(7) 0.7013(5) 0.106(3) Uani 1 1 d . . . O4 O 1.1540(12) 1.0220(11) 0.6450(6) 0.154(4) Uani 1 1 d . . . C25 C 0.9938(16) 0.9728(17) 0.7316(11) 0.178(9) Uani 1 1 d . . . H25A H 0.9436 0.9068 0.7534 0.214 Uiso 1 1 calc R . . H25B H 1.0616 1.0244 0.7715 0.214 Uiso 1 1 calc R . . C26 C 1.0794(15) 0.9296(13) 0.6753(11) 0.163(8) Uani 1 1 d . . . H26A H 1.1508 0.8865 0.6982 0.196 Uiso 1 1 calc R . . H26B H 1.0125 0.8762 0.6359 0.196 Uiso 1 1 calc R . . C27 C 1.040(3) 1.0844(16) 0.6135(11) 0.183(9) Uani 1 1 d . . . H27A H 1.0886 1.1504 0.5909 0.220 Uiso 1 1 calc R . . H27B H 0.9721 1.0318 0.5742 0.220 Uiso 1 1 calc R . . C28 C 0.959(2) 1.1262(12) 0.6691(10) 0.163(8) Uani 1 1 d . . . H28A H 1.0260 1.1811 0.7076 0.196 Uiso 1 1 calc R . . H28B H 0.8850 1.1678 0.6466 0.196 Uiso 1 1 calc R . . O5 O 1.3221(9) 1.0114(6) 0.8608(4) 0.089(2) Uani 1 1 d . . . O6 O 1.2579(9) 1.0083(6) 1.0069(4) 0.093(2) Uani 1 1 d . . . C29 C 1.3330(12) 0.9156(8) 0.8983(6) 0.079(3) Uani 1 1 d . . . H29A H 1.4354 0.9221 0.9219 0.095 Uiso 1 1 calc R . . H29B H 1.3083 0.8444 0.8626 0.095 Uiso 1 1 calc R . . C30 C 1.2328(13) 0.9069(9) 0.9558(6) 0.088(3) Uani 1 1 d . . . H30A H 1.1298 0.8922 0.9316 0.106 Uiso 1 1 calc R . . H30B H 1.2470 0.8405 0.9825 0.106 Uiso 1 1 calc R . . C31 C 1.2512(16) 1.1054(10) 0.9683(7) 0.103(4) Uani 1 1 d . . . H31A H 1.2764 1.1767 1.0040 0.123 Uiso 1 1 calc R . . H31B H 1.1495 1.1003 0.9440 0.123 Uiso 1 1 calc R . . C32 C 1.3515(15) 1.1127(9) 0.9125(7) 0.097(4) Uani 1 1 d . . . H32A H 1.3411 1.1802 0.8862 0.116 Uiso 1 1 calc R . . H32B H 1.4540 1.1243 0.9370 0.116 Uiso 1 1 calc R . . C33 C 0.6408(18) 1.0057(19) 0.4882(9) 0.184(9) Uani 1 1 d . . . H33A H 0.7174 0.9649 0.4712 0.221 Uiso 1 1 calc R . . H33B H 0.6868 1.0874 0.5048 0.221 Uiso 1 1 calc R . . C34 C 0.586(2) 0.9554(14) 0.5480(9) 0.144(6) Uani 1 1 d . . . H34A H 0.5531 0.8715 0.5329 0.173 Uiso 1 1 calc R . . H34B H 0.6675 0.9655 0.5892 0.173 Uiso 1 1 calc R . . O7 O 0.4743(14) 0.9996(10) 0.5727(5) 0.149(4) Uani 1 1 d . . . I3 I 0.96848(5) 0.34870(4) 0.21849(3) 0.03821(14) 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 I1 0.0312(3) 0.0392(3) 0.0344(2) 0.0125(2) 0.00480(19) 0.0138(2) I2 0.0399(3) 0.1155(5) 0.0306(3) 0.0119(3) 0.0053(2) 0.0275(3) F1 0.052(3) 0.040(2) 0.037(2) -0.0013(19) -0.002(2) -0.010(2) F2 0.045(3) 0.047(3) 0.049(3) 0.007(2) 0.004(2) -0.011(2) F3 0.055(3) 0.048(3) 0.031(2) -0.0065(19) 0.005(2) -0.003(2) F4 0.056(3) 0.038(2) 0.043(2) -0.0040(19) 0.009(2) -0.009(2) F5 0.081(3) 0.032(2) 0.053(3) -0.004(2) 0.010(2) -0.001(2) F6 0.101(4) 0.055(3) 0.048(3) -0.013(2) 0.020(3) 0.024(3) F7 0.088(4) 0.072(3) 0.060(3) 0.016(3) 0.023(3) -0.010(3) F8 0.085(3) 0.032(2) 0.053(3) -0.001(2) 0.018(2) 0.002(2) O1 0.030(2) 0.025(2) 0.027(2) 0.0036(19) 0.001(2) 0.0032(19) O2 0.032(3) 0.030(2) 0.025(2) 0.0041(19) 0.001(2) 0.013(2) N1 0.057(4) 0.013(3) 0.083(5) 0.009(3) -0.008(4) 0.009(3) N2 0.067(5) 0.018(3) 0.115(7) 0.011(4) -0.024(5) 0.010(3) C1 0.029(4) 0.025(3) 0.028(4) -0.001(3) -0.006(3) 0.002(3) C2 0.027(4) 0.023(3) 0.038(4) 0.003(3) -0.007(3) 0.001(3) C3 0.027(4) 0.036(4) 0.035(4) 0.013(3) 0.010(3) 0.014(3) C4 0.031(4) 0.040(4) 0.027(4) 0.008(3) 0.004(3) 0.015(3) C5 0.026(4) 0.023(3) 0.042(4) 0.001(3) 0.003(3) 0.004(3) C6 0.024(3) 0.024(3) 0.029(3) 0.005(3) -0.002(3) 0.007(3) C7 0.041(5) 0.059(5) 0.040(4) 0.008(4) 0.002(4) 0.009(4) C8 0.045(5) 0.021(4) 0.063(5) 0.004(3) -0.012(4) 0.012(3) C9 0.047(5) 0.018(3) 0.060(5) 0.006(3) -0.013(4) 0.009(3) C10 0.056(5) 0.019(4) 0.084(6) 0.004(4) -0.013(5) 0.005(4) C11 0.057(5) 0.031(4) 0.066(5) 0.010(4) -0.007(4) 0.022(4) C12 0.051(5) 0.037(4) 0.062(5) 0.001(4) -0.008(4) 0.019(4) C13 0.039(4) 0.042(4) 0.042(4) 0.002(3) 0.002(3) 0.009(3) C14 0.056(5) 0.017(3) 0.051(5) -0.001(3) -0.016(4) 0.012(3) C15 0.044(4) 0.019(3) 0.052(5) -0.002(3) -0.005(4) 0.011(3) C16 0.055(5) 0.018(4) 0.082(6) 0.009(4) -0.007(5) 0.001(3) C17 0.070(6) 0.031(4) 0.086(7) 0.004(4) -0.031(5) 0.024(4) C18 0.057(5) 0.027(4) 0.075(6) 0.001(4) -0.031(5) 0.013(4) C19 0.031(4) 0.034(4) 0.027(3) 0.008(3) 0.000(3) 0.017(3) C20 0.044(4) 0.029(4) 0.033(4) 0.003(3) -0.004(3) 0.011(3) C21 0.054(5) 0.045(4) 0.024(4) -0.009(3) -0.001(3) 0.023(4) C22 0.028(4) 0.065(5) 0.028(4) 0.010(4) -0.003(3) 0.021(4) C23 0.039(4) 0.048(5) 0.043(4) 0.013(4) 0.003(4) 0.004(4) C24 0.047(5) 0.035(4) 0.036(4) 0.004(3) 0.002(3) 0.015(3) O3 0.115(7) 0.077(5) 0.128(7) 0.035(5) 0.007(5) 0.016(5) O4 0.131(9) 0.185(11) 0.118(8) 0.032(8) 0.023(7) -0.056(8) C25 0.098(11) 0.25(2) 0.24(2) 0.182(18) 0.068(13) 0.081(13) C26 0.077(9) 0.146(13) 0.30(2) 0.131(16) 0.071(12) 0.030(9) C27 0.30(3) 0.144(16) 0.135(16) 0.085(13) 0.059(18) 0.056(17) C28 0.27(2) 0.065(9) 0.144(15) -0.014(10) 0.056(16) -0.004(11) O5 0.121(6) 0.070(5) 0.074(5) -0.008(4) -0.008(4) 0.031(4) O6 0.127(7) 0.071(5) 0.074(5) -0.008(4) 0.006(4) 0.018(5) C29 0.092(8) 0.053(6) 0.084(8) -0.016(5) -0.007(6) 0.016(6) C30 0.100(9) 0.054(6) 0.098(9) -0.012(6) 0.001(7) 0.000(6) C31 0.147(12) 0.078(8) 0.089(9) -0.009(7) 0.007(8) 0.055(8) C32 0.133(11) 0.051(6) 0.101(9) 0.004(6) -0.010(8) 0.023(7) C33 0.140(14) 0.33(3) 0.119(13) 0.133(16) 0.019(11) 0.085(16) C34 0.203(19) 0.131(13) 0.106(12) 0.037(10) -0.013(12) 0.062(13) O7 0.196(11) 0.218(12) 0.063(6) 0.031(6) 0.004(6) 0.126(10) I3 0.0370(3) 0.0435(3) 0.0377(3) 0.0090(2) 0.0098(2) 0.0119(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I1 C3 2.104(6) . ? I2 C22 2.096(7) . ? F1 C1 1.345(7) . ? F2 C2 1.343(7) . ? F3 C4 1.349(7) . ? F4 C5 1.350(7) . ? F5 C20 1.345(8) . ? F6 C21 1.347(8) . ? F7 C23 1.340(8) . ? F8 C24 1.351(8) . ? O1 C6 1.360(7) . ? O1 C7 1.430(8) . ? O2 C19 1.355(7) . ? O2 C13 1.459(8) . ? N1 C11 1.315(10) . ? N1 C10 1.321(9) . ? N1 H1N 1.331(9) . ? N2 C17 1.313(10) . ? N2 C16 1.340(10) . ? C1 C2 1.363(9) . ? C1 C6 1.384(9) . ? C2 C3 1.399(9) . ? C3 C4 1.378(9) . ? C4 C5 1.378(9) . ? C5 C6 1.395(9) . ? C7 C13 1.473(10) . ? C7 C8 1.589(10) . ? C7 H7 1.0000 . ? C8 C9 1.357(10) . ? C8 C12 1.380(9) . ? C9 C10 1.369(9) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C11 C12 1.385(10) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C14 1.550(9) . ? C13 H13 1.0000 . ? C14 C15 1.379(10) . ? C14 C18 1.385(10) . ? C15 C16 1.367(9) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 C18 1.364(10) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? C19 C24 1.382(9) . ? C19 C20 1.400(9) . ? C20 C21 1.365(10) . ? C21 C22 1.378(10) . ? C22 C23 1.353(10) . ? C23 C24 1.378(10) . ? O3 C28 1.403(16) . ? O3 C25 1.422(14) . ? O4 C26 1.399(14) . ? O4 C27 1.49(2) . ? C25 C26 1.48(2) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C27 C28 1.44(2) . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? O5 C29 1.402(11) . ? O5 C32 1.417(12) . ? O6 C30 1.414(11) . ? O6 C31 1.422(13) . ? C29 C30 1.492(15) . ? C29 H29A 0.9900 . ? C29 H29B 0.9900 . ? C30 H30A 0.9900 . ? C30 H30B 0.9900 . ? C31 C32 1.469(16) . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C33 C34 1.413(19) . ? C33 O7 1.448(16) 2_676 ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C34 O7 1.349(17) . ? C34 H34A 0.9900 . ? C34 H34B 0.9900 . ? O7 C33 1.448(16) 2_676 ? 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 C6 O1 C7 119.7(5) . . ? C19 O2 C13 114.0(5) . . ? C11 N1 C10 121.4(6) . . ? C11 N1 H1N 117(4) . . ? C10 N1 H1N 122(4) . . ? C17 N2 C16 118.6(6) . . ? F1 C1 C2 118.7(6) . . ? F1 C1 C6 119.2(6) . . ? C2 C1 C6 122.0(6) . . ? F2 C2 C1 118.9(6) . . ? F2 C2 C3 119.2(6) . . ? C1 C2 C3 121.9(6) . . ? C4 C3 C2 116.2(6) . . ? C4 C3 I1 121.2(5) . . ? C2 C3 I1 122.5(5) . . ? F3 C4 C5 117.7(6) . . ? F3 C4 C3 120.3(6) . . ? C5 C4 C3 122.1(6) . . ? F4 C5 C4 118.2(6) . . ? F4 C5 C6 120.4(6) . . ? C4 C5 C6 121.4(6) . . ? O1 C6 C1 117.6(5) . . ? O1 C6 C5 125.9(6) . . ? C1 C6 C5 116.5(6) . . ? O1 C7 C13 110.8(6) . . ? O1 C7 C8 108.7(6) . . ? C13 C7 C8 108.3(6) . . ? O1 C7 H7 109.7 . . ? C13 C7 H7 109.7 . . ? C8 C7 H7 109.7 . . ? C9 C8 C12 120.3(6) . . ? C9 C8 C7 118.6(6) . . ? C12 C8 C7 121.0(7) . . ? C8 C9 C10 118.8(7) . . ? C8 C9 H9 120.6 . . ? C10 C9 H9 120.6 . . ? N1 C10 C9 120.8(7) . . ? N1 C10 H10 119.6 . . ? C9 C10 H10 119.6 . . ? N1 C11 C12 120.9(7) . . ? N1 C11 H11 119.6 . . ? C12 C11 H11 119.6 . . ? C8 C12 C11 117.6(7) . . ? C8 C12 H12 121.2 . . ? C11 C12 H12 121.2 . . ? O2 C13 C7 109.4(6) . . ? O2 C13 C14 111.3(6) . . ? C7 C13 C14 107.8(6) . . ? O2 C13 H13 109.4 . . ? C7 C13 H13 109.4 . . ? C14 C13 H13 109.4 . . ? C15 C14 C18 118.1(6) . . ? C15 C14 C13 123.1(6) . . ? C18 C14 C13 118.8(7) . . ? C16 C15 C14 119.4(7) . . ? C16 C15 H15 120.3 . . ? C14 C15 H15 120.3 . . ? N2 C16 C15 121.8(7) . . ? N2 C16 H16 119.1 . . ? C15 C16 H16 119.1 . . ? N2 C17 C18 123.2(7) . . ? N2 C17 H17 118.4 . . ? C18 C17 H17 118.4 . . ? C17 C18 C14 118.8(7) . . ? C17 C18 H18 120.6 . . ? C14 C18 H18 120.6 . . ? O2 C19 C24 122.2(6) . . ? O2 C19 C20 121.7(6) . . ? C24 C19 C20 115.9(6) . . ? F5 C20 C21 119.9(6) . . ? F5 C20 C19 118.8(6) . . ? C21 C20 C19 121.2(7) . . ? F6 C21 C20 117.0(7) . . ? F6 C21 C22 121.2(7) . . ? C20 C21 C22 121.8(7) . . ? C23 C22 C21 117.6(7) . . ? C23 C22 I2 124.7(6) . . ? C21 C22 I2 117.7(5) . . ? F7 C23 C22 120.4(7) . . ? F7 C23 C24 118.1(7) . . ? C22 C23 C24 121.5(7) . . ? F8 C24 C23 119.7(7) . . ? F8 C24 C19 118.3(6) . . ? C23 C24 C19 122.0(7) . . ? C28 O3 C25 109.1(12) . . ? C26 O4 C27 106.6(12) . . ? O3 C25 C26 112.0(14) . . ? O3 C25 H25A 109.2 . . ? C26 C25 H25A 109.2 . . ? O3 C25 H25B 109.2 . . ? C26 C25 H25B 109.2 . . ? H25A C25 H25B 107.9 . . ? O4 C26 C25 110.1(15) . . ? O4 C26 H26A 109.6 . . ? C25 C26 H26A 109.6 . . ? O4 C26 H26B 109.6 . . ? C25 C26 H26B 109.6 . . ? H26A C26 H26B 108.2 . . ? C28 C27 O4 111.6(16) . . ? C28 C27 H27A 109.3 . . ? O4 C27 H27A 109.3 . . ? C28 C27 H27B 109.3 . . ? O4 C27 H27B 109.3 . . ? H27A C27 H27B 108.0 . . ? O3 C28 C27 110.3(12) . . ? O3 C28 H28A 109.6 . . ? C27 C28 H28A 109.6 . . ? O3 C28 H28B 109.6 . . ? C27 C28 H28B 109.6 . . ? H28A C28 H28B 108.1 . . ? C29 O5 C32 109.2(8) . . ? C30 O6 C31 109.4(8) . . ? O5 C29 C30 111.6(9) . . ? O5 C29 H29A 109.3 . . ? C30 C29 H29A 109.3 . . ? O5 C29 H29B 109.3 . . ? C30 C29 H29B 109.3 . . ? H29A C29 H29B 108.0 . . ? O6 C30 C29 112.2(9) . . ? O6 C30 H30A 109.2 . . ? C29 C30 H30A 109.2 . . ? O6 C30 H30B 109.2 . . ? C29 C30 H30B 109.2 . . ? H30A C30 H30B 107.9 . . ? O6 C31 C32 112.3(9) . . ? O6 C31 H31A 109.1 . . ? C32 C31 H31A 109.1 . . ? O6 C31 H31B 109.1 . . ? C32 C31 H31B 109.1 . . ? H31A C31 H31B 107.9 . . ? O5 C32 C31 111.4(10) . . ? O5 C32 H32A 109.3 . . ? C31 C32 H32A 109.3 . . ? O5 C32 H32B 109.3 . . ? C31 C32 H32B 109.3 . . ? H32A C32 H32B 108.0 . . ? C34 C33 O7 111.7(15) . 2_676 ? C34 C33 H33A 109.3 . . ? O7 C33 H33A 109.3 2_676 . ? C34 C33 H33B 109.3 . . ? O7 C33 H33B 109.3 2_676 . ? H33A C33 H33B 107.9 . . ? O7 C34 C33 114.4(13) . . ? O7 C34 H34A 108.7 . . ? C33 C34 H34A 108.7 . . ? O7 C34 H34B 108.7 . . ? C33 C34 H34B 108.7 . . ? H34A C34 H34B 107.6 . . ? C34 O7 C33 109.5(12) . 2_676 ? 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 F1 C1 C2 F2 0.9(9) . . . . ? C6 C1 C2 F2 178.5(5) . . . . ? F1 C1 C2 C3 -178.6(5) . . . . ? C6 C1 C2 C3 -1.0(10) . . . . ? F2 C2 C3 C4 -177.7(5) . . . . ? C1 C2 C3 C4 1.8(9) . . . . ? F2 C2 C3 I1 -1.3(8) . . . . ? C1 C2 C3 I1 178.2(5) . . . . ? C2 C3 C4 F3 179.0(5) . . . . ? I1 C3 C4 F3 2.6(8) . . . . ? C2 C3 C4 C5 -1.1(9) . . . . ? I1 C3 C4 C5 -177.5(5) . . . . ? F3 C4 C5 F4 -2.6(8) . . . . ? C3 C4 C5 F4 177.5(6) . . . . ? F3 C4 C5 C6 179.4(5) . . . . ? C3 C4 C5 C6 -0.4(10) . . . . ? C7 O1 C6 C1 -148.3(6) . . . . ? C7 O1 C6 C5 34.9(8) . . . . ? F1 C1 C6 O1 -0.1(8) . . . . ? C2 C1 C6 O1 -177.7(5) . . . . ? F1 C1 C6 C5 177.0(5) . . . . ? C2 C1 C6 C5 -0.6(9) . . . . ? F4 C5 C6 O1 0.2(9) . . . . ? C4 C5 C6 O1 178.1(6) . . . . ? F4 C5 C6 C1 -176.6(5) . . . . ? C4 C5 C6 C1 1.3(9) . . . . ? C6 O1 C7 C13 133.1(6) . . . . ? C6 O1 C7 C8 -108.1(6) . . . . ? O1 C7 C8 C9 144.2(7) . . . . ? C13 C7 C8 C9 -95.4(9) . . . . ? O1 C7 C8 C12 -34.2(10) . . . . ? C13 C7 C8 C12 86.2(9) . . . . ? C12 C8 C9 C10 4.4(13) . . . . ? C7 C8 C9 C10 -174.0(8) . . . . ? C11 N1 C10 C9 1.8(14) . . . . ? C8 C9 C10 N1 -5.2(13) . . . . ? C10 N1 C11 C12 2.4(13) . . . . ? C9 C8 C12 C11 -0.4(13) . . . . ? C7 C8 C12 C11 178.0(7) . . . . ? N1 C11 C12 C8 -3.1(13) . . . . ? C19 O2 C13 C7 155.1(6) . . . . ? C19 O2 C13 C14 -85.8(7) . . . . ? O1 C7 C13 O2 60.4(7) . . . . ? C8 C7 C13 O2 -58.7(7) . . . . ? O1 C7 C13 C14 -60.7(7) . . . . ? C8 C7 C13 C14 -179.8(6) . . . . ? O2 C13 C14 C15 -40.7(10) . . . . ? C7 C13 C14 C15 79.3(9) . . . . ? O2 C13 C14 C18 137.4(7) . . . . ? C7 C13 C14 C18 -102.6(9) . . . . ? C18 C14 C15 C16 -4.1(12) . . . . ? C13 C14 C15 C16 173.9(8) . . . . ? C17 N2 C16 C15 0.5(14) . . . . ? C14 C15 C16 N2 2.2(13) . . . . ? C16 N2 C17 C18 -1.2(16) . . . . ? N2 C17 C18 C14 -0.9(16) . . . . ? C15 C14 C18 C17 3.5(13) . . . . ? C13 C14 C18 C17 -174.6(8) . . . . ? C13 O2 C19 C24 -87.7(7) . . . . ? C13 O2 C19 C20 97.4(7) . . . . ? O2 C19 C20 F5 -1.7(9) . . . . ? C24 C19 C20 F5 -176.9(6) . . . . ? O2 C19 C20 C21 175.6(6) . . . . ? C24 C19 C20 C21 0.4(9) . . . . ? F5 C20 C21 F6 -2.8(10) . . . . ? C19 C20 C21 F6 180.0(6) . . . . ? F5 C20 C21 C22 177.1(6) . . . . ? C19 C20 C21 C22 -0.1(10) . . . . ? F6 C21 C22 C23 179.4(6) . . . . ? C20 C21 C22 C23 -0.5(10) . . . . ? F6 C21 C22 I2 1.4(9) . . . . ? C20 C21 C22 I2 -178.5(5) . . . . ? C21 C22 C23 F7 -179.0(6) . . . . ? I2 C22 C23 F7 -1.1(10) . . . . ? C21 C22 C23 C24 0.8(10) . . . . ? I2 C22 C23 C24 178.7(5) . . . . ? F7 C23 C24 F8 0.0(10) . . . . ? C22 C23 C24 F8 -179.8(6) . . . . ? F7 C23 C24 C19 179.3(6) . . . . ? C22 C23 C24 C19 -0.5(11) . . . . ? O2 C19 C24 F8 4.0(9) . . . . ? C20 C19 C24 F8 179.2(6) . . . . ? O2 C19 C24 C23 -175.3(6) . . . . ? C20 C19 C24 C23 -0.1(10) . . . . ? C28 O3 C25 C26 -57.8(18) . . . . ? C27 O4 C26 C25 -57.8(18) . . . . ? O3 C25 C26 O4 60(2) . . . . ? C26 O4 C27 C28 59(2) . . . . ? C25 O3 C28 C27 58(2) . . . . ? O4 C27 C28 O3 -60(2) . . . . ? C32 O5 C29 C30 56.6(12) . . . . ? C31 O6 C30 C29 53.4(13) . . . . ? O5 C29 C30 O6 -56.3(12) . . . . ? C30 O6 C31 C32 -54.5(14) . . . . ? C29 O5 C32 C31 -57.4(12) . . . . ? O6 C31 C32 O5 57.5(14) . . . . ? O7 C33 C34 O7 -55(2) 2_676 . . . ? C33 C34 O7 C33 54(2) . . . 2_676 ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 1.379 _refine_diff_density_min -1.368 _refine_diff_density_rms 0.130 data_jm056 _database_code_depnum_ccdc_archive 'CCDC 866319' #TrackingRef 'JM056.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H11 N2 O2 F8 I2 1+, 2(C6 H5 N O2), I 1-' _chemical_formula_sum 'C36 H21 F8 I3 N4 O6' _chemical_formula_weight 1138.27 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.004(2) _cell_length_b 11.872(2) _cell_length_c 19.283(4) _cell_angle_alpha 94.51(2) _cell_angle_beta 91.37(2) _cell_angle_gamma 107.65(2) _cell_volume 1955.7(7) _cell_formula_units_Z 2 _cell_measurement_temperature 103(2) _cell_measurement_reflns_used 8098 _cell_measurement_theta_min 2.38 _cell_measurement_theta_max 24.29 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.933 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1088 _exptl_absorpt_coefficient_mu 2.485 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.' _exptl_absorpt_correction_T_min 0.4629 _exptl_absorpt_correction_T_max 0.5694 _exptl_special_details ; The crystals were prepared starting from the omologous compound containing a ratios 1:1:2.5 of C24H10N2O2F8I2:HI:C4H4O2 by immerging some crystals in nitrobenzene. After one day some small crystals were tested. They diffract very badly and at very low angle. A number of attemp to collect data at low temperature failed due to the extremely large mosaicity of the material. Always, also at -103 K, the diffraction pattern was nearly zero over 2\t = 45\%. At the end we decided to collect the data using a sample whose mosaicity gave us the hope to manage the integration of a significant part of the reflections. In spite the data quality was very low, the resolution was easy and showed immediately the main molecule, one nitrobenzene molecule, implied in very weak bond to the acid H in between the pyridine N atoms, and part of the second nitrobenzene. ; _diffrn_ambient_temperature 103(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_standards_decay_% 0.00 _diffrn_reflns_number 14882 _diffrn_reflns_av_R_equivalents 0.0328 _diffrn_reflns_av_sigmaI/netI 0.0384 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.38 _diffrn_reflns_theta_max 24.41 _reflns_number_total 4332 _reflns_number_gt 3504 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution ; SIR2002 (Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103.) ; _computing_structure_refinement 'SHELXL (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122)' _computing_molecular_graphics ; ORTEP-3 (Farrugia, L.J. (1997) Jour. Appl. Cryst. 30, 565) Mercury (Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457 ; _computing_publication_material SHELXTL _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. The refinement was very hard due the poor quality of the data, and the difficulty to modelyze the second nitrobenzene, very mobile and disoreded. This last molecule is distributed over two positions, having in common only the zone of the nitrogroup, but with very different orientation and mass centre. Due to all these problems, the refinement was carried on with a lot of restraints, on ADPs of all heavy atoms, the geometry of the disordered nitro group of the first nitrobenzene and of all the second nitrobenzene. Only the H atom in between the pyridine N atoms was refined but with strong restraints, imposing similar distances N1-H1N and N2(x,-1+y,z)-H1N. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0051P)^2^+78.5045P] 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 ? _refine_ls_number_reflns 4332 _refine_ls_number_parameters 627 _refine_ls_number_restraints 658 _refine_ls_R_factor_all 0.1049 _refine_ls_R_factor_gt 0.0830 _refine_ls_wR_factor_ref 0.1941 _refine_ls_wR_factor_gt 0.1806 _refine_ls_goodness_of_fit_ref 1.254 _refine_ls_restrained_S_all 1.178 _refine_ls_shift/su_max 0.007 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I1 I 0.35964(14) 0.45873(12) -0.13722(7) 0.0469(4) Uani 1 1 d . . . I2 I -0.41503(15) 0.38958(14) 0.54843(8) 0.0572(4) Uani 1 1 d . . . F1 F 0.3518(10) 0.7043(8) 0.1117(6) 0.041(2) Uani 1 1 d U . . F2 F 0.4737(11) 0.6707(9) -0.0114(6) 0.047(2) Uani 1 1 d U . . F3 F 0.0694(10) 0.3079(8) -0.0607(6) 0.042(2) Uani 1 1 d U . . F4 F -0.0461(10) 0.3395(8) 0.0616(6) 0.041(2) Uani 1 1 d U . . F5 F 0.0506(12) 0.6591(9) 0.4064(6) 0.051(3) Uani 1 1 d U . . F6 F -0.1079(13) 0.6000(10) 0.5192(7) 0.061(3) Uani 1 1 d U . . F7 F -0.4633(10) 0.2709(10) 0.3897(6) 0.053(3) Uani 1 1 d U . . F8 F -0.3014(10) 0.3276(9) 0.2758(6) 0.045(2) Uani 1 1 d U . . O1 O 0.0854(12) 0.5348(9) 0.1528(7) 0.0342(18) Uani 1 1 d U . . O2 O -0.0496(12) 0.5140(9) 0.2772(7) 0.0365(18) Uani 1 1 d U . . N1 N 0.1691(15) 0.1691(10) 0.2341(9) 0.040(2) Uani 1 1 d DU . . H1N H 0.166(3) 0.0572(9) 0.242(4) 0.01(3) Uiso 1 1 d D . . N2 N 0.1627(16) 0.9442(11) 0.2442(9) 0.044(2) Uani 1 1 d U . . C1 C 0.2847(18) 0.6050(14) 0.0703(10) 0.035(2) Uani 1 1 d U . . C2 C 0.3410(17) 0.5868(14) 0.0075(10) 0.033(2) Uani 1 1 d U . . C3 C 0.2773(18) 0.4859(14) -0.0386(10) 0.035(2) Uani 1 1 d U . . C4 C 0.1406(19) 0.4064(15) -0.0160(11) 0.037(2) Uani 1 1 d U . . C5 C 0.0891(18) 0.4207(14) 0.0456(10) 0.033(2) Uani 1 1 d U . . C6 C 0.1572(18) 0.5205(14) 0.0917(10) 0.0331(19) Uani 1 1 d U . . C7 C 0.1750(19) 0.5264(15) 0.2128(11) 0.0409(19) Uani 1 1 d U . . H7 H 0.2864 0.5731 0.2075 0.049 Uiso 1 1 calc R . . C9 C 0.029(2) 0.3041(14) 0.2074(11) 0.044(2) Uani 1 1 d U . . H9 H -0.0654 0.3188 0.1940 0.053 Uiso 1 1 calc R . . C10 C 0.0370(19) 0.1879(13) 0.2105(11) 0.042(2) Uani 1 1 d DU . . H10 H -0.0514 0.1221 0.1958 0.051 Uiso 1 1 calc R . . C11 C 0.2932(19) 0.2557(11) 0.2552(11) 0.041(2) Uani 1 1 d DU . . H11 H 0.3814 0.2390 0.2746 0.049 Uiso 1 1 calc R . . C8 C 0.1673(19) 0.3972(14) 0.2253(11) 0.043(2) Uani 1 1 d U . . C12 C 0.297(2) 0.3728(14) 0.2495(11) 0.043(2) Uani 1 1 d U . . H12 H 0.3905 0.4357 0.2623 0.052 Uiso 1 1 calc R . . C13 C 0.1166(19) 0.5795(15) 0.2766(11) 0.0422(19) Uani 1 1 d U . . H13 H 0.1748 0.5737 0.3203 0.051 Uiso 1 1 calc R . . C14 C 0.133(2) 0.7098(15) 0.2642(12) 0.045(2) Uani 1 1 d U . . C15 C 0.014(2) 0.7435(15) 0.2344(11) 0.046(2) Uani 1 1 d U . . H15 H -0.0813 0.6845 0.2190 0.055 Uiso 1 1 calc R . . C16 C 0.0300(19) 0.8599(12) 0.2268(11) 0.043(2) Uani 1 1 d U . . H16 H -0.0560 0.8808 0.2085 0.051 Uiso 1 1 calc R . . C17 C 0.281(2) 0.9169(15) 0.2702(12) 0.049(2) Uani 1 1 d U . . H17 H 0.3734 0.9786 0.2852 0.059 Uiso 1 1 calc R . . C18 C 0.275(2) 0.8016(15) 0.2766(12) 0.049(2) Uani 1 1 d U . . H18 H 0.3667 0.7835 0.2894 0.058 Uiso 1 1 calc R . . C19 C -0.1192(18) 0.4935(15) 0.3381(11) 0.0372(19) Uani 1 1 d U . . C20 C -0.0743(19) 0.5612(16) 0.4014(11) 0.041(2) Uani 1 1 d U . . C21 C -0.159(2) 0.5283(17) 0.4600(12) 0.044(2) Uani 1 1 d U . . C22 C -0.2875(19) 0.4324(16) 0.4594(11) 0.043(2) Uani 1 1 d U . . C23 C -0.3321(19) 0.3646(16) 0.3960(11) 0.043(2) Uani 1 1 d U . . C24 C -0.2517(19) 0.3944(16) 0.3366(11) 0.038(2) Uani 1 1 d U . . I3 I 0.61121(12) 0.67382(10) 0.30301(7) 0.0356(3) Uani 1 1 d . . . C25 C 0.7384(19) 0.9828(11) 0.0258(8) 0.060(3) Uani 1 1 d DU . . C26 C 0.720(2) 0.9084(14) 0.0778(6) 0.057(4) Uani 1 1 d DU A . H26 H 0.7487 0.8377 0.0725 0.069 Uiso 1 1 calc R . . C27 C 0.658(2) 0.9396(13) 0.1379(8) 0.060(4) Uani 1 1 d DU . . H27 H 0.6408 0.8894 0.1748 0.072 Uiso 1 1 calc R A . C28 C 0.621(2) 1.0440(12) 0.1446(9) 0.060(4) Uani 1 1 d DU A . H28 H 0.5801 1.0663 0.1866 0.072 Uiso 1 1 calc R . . C29 C 0.643(2) 1.1160(15) 0.0912(7) 0.061(4) Uani 1 1 d DU . . H29 H 0.6181 1.1883 0.0972 0.073 Uiso 1 1 calc R A . C30 C 0.700(2) 1.0862(13) 0.0296(9) 0.061(4) Uani 1 1 d DU A . H30 H 0.7117 1.1342 -0.0083 0.073 Uiso 1 1 calc R . . N3A N 0.7936(19) 0.9430(13) -0.0452(9) 0.068(4) Uani 0.50 1 d PDU A 1 O3A O 0.782(3) 1.005(2) -0.0936(10) 0.073(6) Uani 0.50 1 d PDU A 1 O4A O 0.879(3) 0.877(2) -0.0415(13) 0.065(6) Uani 0.50 1 d PDU A 1 N3B N 0.817(4) 0.9452(12) -0.0381(13) 0.069(4) Uani 0.50 1 d PDU A 2 O3B O 0.868(4) 1.018(2) -0.0822(15) 0.075(6) Uani 0.50 1 d PDU A 2 O4B O 0.804(4) 0.8365(17) -0.0465(18) 0.067(6) Uani 0.50 1 d PDU A 2 C31 C -0.091(2) 0.0352(11) 0.3820(16) 0.096(5) Uani 0.705(10) 1 d PDU B -1 C32 C 0.0082(17) 0.1492(14) 0.3911(18) 0.094(5) Uani 0.705(10) 1 d PDU B -1 H32 H -0.0241 0.2148 0.3795 0.113 Uiso 0.705(10) 1 calc PR B -1 C33 C 0.1565(19) 0.1641(16) 0.4176(17) 0.086(6) Uani 0.705(10) 1 d PDU B -1 H33 H 0.2287 0.2415 0.4256 0.103 Uiso 0.705(10) 1 calc PR B -1 C34 C 0.200(2) 0.0677(15) 0.4325(18) 0.086(6) Uani 0.705(10) 1 d PDU B -1 H34 H 0.3058 0.0777 0.4467 0.103 Uiso 0.705(10) 1 calc PR B -1 C35 C 0.0935(18) -0.0435(17) 0.4272(18) 0.088(6) Uani 0.705(10) 1 d PDU B -1 H35 H 0.1253 -0.1093 0.4388 0.106 Uiso 0.705(10) 1 calc PR B -1 C36 C -0.058(2) -0.0610(17) 0.4055(19) 0.091(6) Uani 0.705(10) 1 d PDU B -1 H36 H -0.1362 -0.1355 0.4066 0.109 Uiso 0.705(10) 1 calc PR B -1 N4 N -0.264(2) 0.0200(15) 0.3601(13) 0.101(4) Uani 0.705(10) 1 d PDU B -1 O5 O -0.282(3) 0.094(2) 0.3204(15) 0.104(6) Uani 0.705(10) 1 d PDU B -1 O6 O -0.366(2) -0.047(2) 0.3941(16) 0.112(6) Uani 0.705(10) 1 d PDU B -1 C37 C -0.360(4) 0.056(3) 0.4265(11) 0.099(5) Uani 0.295(10) 1 d PDU B -2 C38 C -0.290(4) 0.126(4) 0.4863(10) 0.098(6) Uani 0.295(10) 1 d PDU B -2 H38 H -0.1992 0.1912 0.4838 0.118 Uiso 0.295(10) 1 calc PR B -2 C39 C -0.354(4) 0.100(4) 0.5496(13) 0.099(7) Uani 0.295(10) 1 d PDU B -2 H39 H -0.3171 0.1538 0.5897 0.119 Uiso 0.295(10) 1 calc PR B -2 C40 C -0.472(6) -0.005(4) 0.5545(16) 0.100(7) Uani 0.295(10) 1 d PDU B -2 H40 H -0.5049 -0.0292 0.5988 0.120 Uiso 0.295(10) 1 calc PR B -2 C41 C -0.542(6) -0.074(4) 0.4946(17) 0.099(7) Uani 0.295(10) 1 d PDU B -2 H41 H -0.6333 -0.1397 0.4971 0.119 Uiso 0.295(10) 1 calc PR B -2 C42 C -0.480(7) -0.047(4) 0.4312(16) 0.099(6) Uani 0.295(10) 1 d PDU B -2 H42 H -0.5193 -0.1000 0.3907 0.119 Uiso 0.295(10) 1 calc PR B -2 N5 N -0.283(3) 0.084(5) 0.354(4) 0.099(5) Uani 0.295(10) 1 d PDU B -2 O7 O -0.154(6) 0.160(5) 0.355(4) 0.091(7) Uani 0.295(10) 1 d PDU B -2 O8 O -0.369(7) 0.012(5) 0.309(3) 0.098(8) Uani 0.295(10) 1 d PDU B -2 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 0.0432(7) 0.0664(8) 0.0388(9) 0.0062(7) 0.0087(6) 0.0272(6) I2 0.0512(7) 0.0922(10) 0.0429(10) 0.0184(8) 0.0224(7) 0.0392(7) F1 0.043(5) 0.026(4) 0.050(6) 0.004(5) 0.002(4) 0.006(4) F2 0.039(5) 0.043(5) 0.053(6) 0.019(5) 0.012(4) 0.003(4) F3 0.042(5) 0.033(5) 0.051(6) 0.003(5) 0.001(4) 0.012(4) F4 0.040(5) 0.031(4) 0.052(6) 0.008(5) 0.009(4) 0.008(4) F5 0.052(5) 0.037(5) 0.055(7) -0.004(5) 0.008(5) 0.002(4) F6 0.065(6) 0.059(6) 0.057(7) -0.010(6) 0.011(5) 0.019(5) F7 0.026(4) 0.067(6) 0.059(6) 0.023(5) 0.017(4) -0.003(4) F8 0.037(5) 0.046(5) 0.046(6) 0.014(5) 0.010(4) 0.003(4) O1 0.030(3) 0.027(3) 0.052(4) 0.012(3) 0.008(3) 0.016(3) O2 0.031(3) 0.030(3) 0.051(4) 0.009(3) 0.015(3) 0.011(3) N1 0.038(4) 0.011(4) 0.068(5) 0.013(4) 0.004(4) 0.000(3) N2 0.038(4) 0.025(4) 0.068(5) 0.002(4) 0.004(4) 0.010(3) C1 0.033(4) 0.028(4) 0.049(4) 0.014(4) 0.004(3) 0.014(3) C2 0.029(4) 0.030(4) 0.047(4) 0.018(4) 0.005(4) 0.016(3) C3 0.031(4) 0.032(4) 0.049(5) 0.013(4) 0.007(4) 0.016(3) C4 0.033(4) 0.032(4) 0.051(4) 0.010(4) 0.004(4) 0.017(3) C5 0.030(4) 0.028(4) 0.049(4) 0.011(4) 0.005(4) 0.018(3) C6 0.030(3) 0.027(3) 0.049(4) 0.012(3) 0.007(3) 0.017(3) C7 0.034(3) 0.030(3) 0.060(4) 0.009(3) 0.006(3) 0.009(3) C9 0.040(4) 0.020(4) 0.069(5) 0.011(4) 0.000(4) 0.003(4) C10 0.038(4) 0.016(4) 0.069(5) 0.012(4) 0.001(4) 0.000(4) C11 0.040(4) 0.013(4) 0.069(5) 0.014(4) 0.000(4) 0.003(4) C8 0.039(3) 0.023(3) 0.067(4) 0.011(3) 0.000(3) 0.007(3) C12 0.041(4) 0.018(4) 0.071(5) 0.012(4) -0.003(4) 0.006(4) C13 0.034(3) 0.032(3) 0.060(4) 0.006(3) 0.008(3) 0.007(3) C14 0.037(3) 0.029(3) 0.069(4) 0.001(3) 0.002(3) 0.010(3) C15 0.038(4) 0.028(4) 0.071(5) 0.001(4) 0.000(4) 0.011(4) C16 0.036(4) 0.025(4) 0.068(5) 0.003(4) 0.000(4) 0.011(4) C17 0.041(4) 0.030(4) 0.072(5) 0.000(4) 0.003(4) 0.007(4) C18 0.039(4) 0.031(4) 0.074(5) -0.001(4) 0.000(4) 0.010(4) C19 0.031(3) 0.036(3) 0.048(4) 0.010(3) 0.014(3) 0.014(3) C20 0.037(4) 0.040(4) 0.049(4) 0.005(4) 0.013(4) 0.014(3) C21 0.039(4) 0.045(4) 0.050(4) 0.003(4) 0.012(4) 0.019(4) C22 0.036(4) 0.047(4) 0.049(5) 0.009(4) 0.011(4) 0.017(4) C23 0.033(4) 0.048(4) 0.049(4) 0.013(4) 0.011(4) 0.013(4) C24 0.031(4) 0.041(4) 0.047(4) 0.013(4) 0.012(4) 0.015(3) I3 0.0311(6) 0.0306(6) 0.0457(9) 0.0044(6) 0.0094(5) 0.0096(5) C25 0.064(6) 0.057(6) 0.059(6) 0.006(6) -0.002(5) 0.019(5) C26 0.062(7) 0.050(7) 0.059(8) 0.008(7) 0.001(6) 0.016(6) C27 0.066(7) 0.054(7) 0.058(8) 0.014(7) 0.004(7) 0.012(6) C28 0.065(7) 0.053(7) 0.060(8) 0.007(7) 0.006(7) 0.016(6) C29 0.071(7) 0.049(7) 0.063(8) 0.008(7) -0.003(7) 0.019(6) C30 0.071(7) 0.050(7) 0.061(8) 0.012(7) -0.002(7) 0.014(6) N3A 0.068(7) 0.071(7) 0.060(7) 0.003(7) -0.001(7) 0.014(6) O3A 0.067(11) 0.086(11) 0.057(11) 0.009(10) -0.005(10) 0.012(10) O4A 0.060(11) 0.076(11) 0.061(11) 0.000(10) 0.003(10) 0.023(9) N3B 0.069(7) 0.071(7) 0.060(7) 0.003(7) -0.001(7) 0.013(7) O3B 0.071(12) 0.082(11) 0.057(11) 0.003(10) -0.009(11) 0.003(11) O4B 0.065(11) 0.070(11) 0.063(11) -0.001(10) 0.013(10) 0.015(10) C31 0.096(7) 0.078(7) 0.097(8) 0.004(7) 0.027(7) 0.004(7) C32 0.091(8) 0.083(8) 0.092(9) 0.006(8) 0.032(8) -0.001(8) C33 0.080(9) 0.077(9) 0.085(10) 0.005(9) 0.035(9) -0.002(9) C34 0.084(9) 0.073(9) 0.083(10) 0.003(9) 0.038(9) -0.003(9) C35 0.092(9) 0.071(9) 0.086(10) 0.000(9) 0.039(9) -0.001(9) C36 0.093(9) 0.071(9) 0.093(10) -0.003(9) 0.035(9) 0.001(9) N4 0.109(7) 0.080(7) 0.103(7) 0.012(7) 0.018(6) 0.009(6) O5 0.119(10) 0.088(10) 0.103(11) 0.019(10) 0.017(10) 0.024(9) O6 0.117(11) 0.087(10) 0.113(11) 0.005(10) 0.017(10) 0.004(10) C37 0.109(7) 0.076(7) 0.104(7) 0.012(7) 0.015(7) 0.013(7) C38 0.109(10) 0.074(10) 0.103(10) 0.011(10) 0.013(10) 0.014(9) C39 0.110(11) 0.073(10) 0.104(11) 0.011(10) 0.012(10) 0.012(10) C40 0.111(11) 0.074(11) 0.104(11) 0.011(11) 0.011(11) 0.010(11) C41 0.110(11) 0.073(10) 0.104(11) 0.012(10) 0.011(10) 0.012(10) C42 0.109(9) 0.076(9) 0.104(10) 0.011(9) 0.013(9) 0.012(9) N5 0.110(8) 0.078(8) 0.102(8) 0.015(8) 0.015(8) 0.017(8) O7 0.106(11) 0.071(11) 0.094(11) 0.022(10) 0.014(11) 0.018(10) O8 0.109(12) 0.078(12) 0.101(13) 0.020(12) 0.013(12) 0.017(12) _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 I1 C3 2.095(19) . ? I2 C22 2.098(18) . ? F1 C1 1.34(2) . ? F2 C2 1.382(17) . ? F3 C4 1.37(2) . ? F4 C5 1.364(17) . ? F5 C20 1.34(2) . ? F6 C21 1.35(2) . ? F7 C23 1.35(2) . ? F8 C24 1.35(2) . ? O1 C6 1.38(2) . ? O1 C7 1.42(2) . ? O2 C19 1.35(2) . ? O2 C13 1.463(19) . ? N1 C11 1.30(2) . ? N1 C10 1.350(19) . ? N1 H1N 1.339(10) . ? N2 C17 1.30(2) . ? N2 C16 1.32(2) . ? C1 C2 1.35(3) . ? C1 C6 1.37(2) . ? C2 C3 1.39(3) . ? C3 C4 1.41(2) . ? C4 C5 1.30(3) . ? C5 C6 1.39(2) . ? C7 C13 1.52(3) . ? C7 C8 1.55(2) . ? C7 H7 1.0000 . ? C9 C8 1.41(2) . ? C9 C10 1.41(2) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C11 C12 1.39(2) . ? C11 H11 0.9500 . ? C8 C12 1.37(2) . ? C12 H12 0.9500 . ? C13 C14 1.55(2) . ? C13 H13 1.0000 . ? C14 C15 1.38(2) . ? C14 C18 1.41(2) . ? C15 C16 1.37(2) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 C18 1.37(2) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? C19 C20 1.39(3) . ? C19 C24 1.40(2) . ? C20 C21 1.40(3) . ? C21 C22 1.35(2) . ? C22 C23 1.39(3) . ? C23 C24 1.38(3) . ? C25 C26 1.369(9) . ? C25 C30 1.371(9) . ? C25 N3B 1.54(3) . ? C25 N3A 1.55(2) . ? C26 C27 1.370(9) . ? C26 H26 0.9500 . ? C27 C28 1.374(9) . ? C27 H27 0.9500 . ? C28 C29 1.369(9) . ? C28 H28 0.9500 . ? C29 C30 1.369(9) . ? C29 H29 0.9500 . ? C30 H30 0.9500 . ? N3A O3A 1.254(13) . ? N3A O4A 1.255(13) . ? N3B O3B 1.256(13) . ? N3B O4B 1.257(13) . ? C31 C36 1.370(9) . ? C31 C32 1.373(9) . ? C31 N4 1.56(2) . ? C32 C33 1.373(9) . ? C32 H32 0.9500 . ? C33 C34 1.368(9) . ? C33 H33 0.9500 . ? C34 C35 1.372(9) . ? C34 H34 0.9500 . ? C35 C36 1.369(9) . ? C35 H35 0.9500 . ? C36 H36 0.9500 . ? N4 O5 1.254(13) . ? N4 O6 1.257(13) . ? C37 C38 1.38(2) . ? C37 C42 1.38(2) . ? C37 N5 1.58(8) . ? C38 C39 1.38(2) . ? C38 H38 0.9500 . ? C39 C40 1.38(2) . ? C39 H39 0.9500 . ? C40 C41 1.38(3) . ? C40 H40 0.9500 . ? C41 C42 1.38(2) . ? C41 H41 0.9500 . ? C42 H42 0.9500 . ? N5 O7 1.24(5) . ? N5 O8 1.24(5) . ? 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 C6 O1 C7 112.5(12) . . ? C19 O2 C13 120.3(15) . . ? C11 N1 C10 122.3(12) . . ? C11 N1 H1N 119.4(14) . . ? C10 N1 H1N 118.1(13) . . ? C17 N2 C16 119.8(13) . . ? F1 C1 C2 120.7(14) . . ? F1 C1 C6 119.8(16) . . ? C2 C1 C6 119.5(18) . . ? C1 C2 F2 118.3(16) . . ? C1 C2 C3 124.1(15) . . ? F2 C2 C3 117.6(15) . . ? C2 C3 C4 113.9(16) . . ? C2 C3 I1 124.4(11) . . ? C4 C3 I1 121.4(14) . . ? C5 C4 F3 121.3(15) . . ? C5 C4 C3 122.3(19) . . ? F3 C4 C3 116.3(16) . . ? C4 C5 F4 117.4(17) . . ? C4 C5 C6 122.7(16) . . ? F4 C5 C6 119.6(15) . . ? C1 C6 O1 123.6(17) . . ? C1 C6 C5 117.3(17) . . ? O1 C6 C5 118.8(14) . . ? O1 C7 C13 109.2(14) . . ? O1 C7 C8 113.7(16) . . ? C13 C7 C8 107.9(15) . . ? O1 C7 H7 108.6 . . ? C13 C7 H7 108.6 . . ? C8 C7 H7 108.6 . . ? C8 C9 C10 116.5(16) . . ? C8 C9 H9 121.7 . . ? C10 C9 H9 121.7 . . ? N1 C10 C9 120.8(15) . . ? N1 C10 H10 119.6 . . ? C9 C10 H10 119.6 . . ? N1 C11 C12 120.3(16) . . ? N1 C11 H11 119.9 . . ? C12 C11 H11 119.9 . . ? C12 C8 C9 120.0(15) . . ? C12 C8 C7 120.2(15) . . ? C9 C8 C7 119.7(15) . . ? C8 C12 C11 119.9(16) . . ? C8 C12 H12 120.1 . . ? C11 C12 H12 120.1 . . ? O2 C13 C7 105.5(15) . . ? O2 C13 C14 108.3(13) . . ? C7 C13 C14 106.9(15) . . ? O2 C13 H13 112.0 . . ? C7 C13 H13 112.0 . . ? C14 C13 H13 112.0 . . ? C15 C14 C18 114.5(16) . . ? C15 C14 C13 122.9(16) . . ? C18 C14 C13 122.4(16) . . ? C16 C15 C14 121.3(17) . . ? C16 C15 H15 119.4 . . ? C14 C15 H15 119.4 . . ? N2 C16 C15 121.4(16) . . ? N2 C16 H16 119.3 . . ? C15 C16 H16 119.3 . . ? N2 C17 C18 121.8(17) . . ? N2 C17 H17 119.1 . . ? C18 C17 H17 119.1 . . ? C17 C18 C14 120.4(17) . . ? C17 C18 H18 119.8 . . ? C14 C18 H18 119.8 . . ? O2 C19 C20 126.9(15) . . ? O2 C19 C24 116.1(18) . . ? C20 C19 C24 116.9(16) . . ? F5 C20 C19 120.2(16) . . ? F5 C20 C21 119.7(19) . . ? C19 C20 C21 120.1(17) . . ? F6 C21 C22 120.4(17) . . ? F6 C21 C20 116.0(17) . . ? C22 C21 C20 124(2) . . ? C21 C22 C23 116.3(17) . . ? C21 C22 I2 122.1(16) . . ? C23 C22 I2 121.6(13) . . ? F7 C23 C24 118(2) . . ? F7 C23 C22 120.3(16) . . ? C24 C23 C22 122.0(18) . . ? F8 C24 C23 119.9(16) . . ? F8 C24 C19 118.9(16) . . ? C23 C24 C19 121(2) . . ? C26 C25 C30 124.7(14) . . ? C26 C25 N3B 114.3(12) . . ? C30 C25 N3B 121.0(12) . . ? C26 C25 N3A 118.2(9) . . ? C30 C25 N3A 116.9(9) . . ? N3B C25 N3A 8.9(16) . . ? C25 C26 C27 117.5(13) . . ? C25 C26 H26 121.3 . . ? C27 C26 H26 121.3 . . ? C26 C27 C28 119.8(14) . . ? C26 C27 H27 120.1 . . ? C28 C27 H27 120.1 . . ? C29 C28 C27 120.5(15) . . ? C29 C28 H28 119.7 . . ? C27 C28 H28 119.7 . . ? C30 C29 C28 121.5(15) . . ? C30 C29 H29 119.2 . . ? C28 C29 H29 119.2 . . ? C29 C30 C25 115.9(14) . . ? C29 C30 H30 122.0 . . ? C25 C30 H30 122.0 . . ? O3A N3A O4A 128(2) . . ? O3A N3A C25 114.3(13) . . ? O4A N3A C25 114.9(13) . . ? O3B N3B O4B 125(2) . . ? O3B N3B C25 119(2) . . ? O4B N3B C25 115.1(18) . . ? C36 C31 C32 124.1(16) . . ? C36 C31 N4 117.4(10) . . ? C32 C31 N4 116.8(11) . . ? C33 C32 C31 117.0(15) . . ? C33 C32 H32 121.5 . . ? C31 C32 H32 121.5 . . ? C34 C33 C32 120.2(15) . . ? C34 C33 H33 119.9 . . ? C32 C33 H33 119.9 . . ? C33 C34 C35 120.5(16) . . ? C33 C34 H34 119.8 . . ? C35 C34 H34 119.8 . . ? C36 C35 C34 121.0(17) . . ? C36 C35 H35 119.5 . . ? C34 C35 H35 119.5 . . ? C35 C36 C31 116.1(16) . . ? C35 C36 H36 121.9 . . ? C31 C36 H36 121.9 . . ? O5 N4 O6 128(2) . . ? O5 N4 C31 114.2(13) . . ? O6 N4 C31 116.3(14) . . ? C38 C37 C42 119.9(8) . . ? C38 C37 N5 119.6(10) . . ? C42 C37 N5 119.7(10) . . ? C37 C38 C39 119.7(8) . . ? C37 C38 H38 120.1 . . ? C39 C38 H38 120.1 . . ? C38 C39 C40 119.8(9) . . ? C38 C39 H39 120.1 . . ? C40 C39 H39 120.1 . . ? C39 C40 C41 119.7(10) . . ? C39 C40 H40 120.1 . . ? C41 C40 H40 120.1 . . ? C42 C41 C40 119.7(10) . . ? C42 C41 H41 120.1 . . ? C40 C41 H41 120.1 . . ? C41 C42 C37 119.9(9) . . ? C41 C42 H42 120.1 . . ? C37 C42 H42 120.1 . . ? O7 N5 O8 134(8) . . ? O7 N5 C37 118(5) . . ? O8 N5 C37 107(4) . . ? 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 F1 C1 C2 F2 3(2) . . . . ? C6 C1 C2 F2 -177.1(13) . . . . ? F1 C1 C2 C3 -179.8(14) . . . . ? C6 C1 C2 C3 0(2) . . . . ? C1 C2 C3 C4 4(2) . . . . ? F2 C2 C3 C4 -178.7(13) . . . . ? C1 C2 C3 I1 178.2(12) . . . . ? F2 C2 C3 I1 -4.6(19) . . . . ? C2 C3 C4 C5 -7(2) . . . . ? I1 C3 C4 C5 178.7(12) . . . . ? C2 C3 C4 F3 177.4(13) . . . . ? I1 C3 C4 F3 3.1(19) . . . . ? F3 C4 C5 F4 -6(2) . . . . ? C3 C4 C5 F4 178.9(13) . . . . ? F3 C4 C5 C6 -178.9(13) . . . . ? C3 C4 C5 C6 6(2) . . . . ? F1 C1 C6 O1 4(2) . . . . ? C2 C1 C6 O1 -175.6(14) . . . . ? F1 C1 C6 C5 178.0(13) . . . . ? C2 C1 C6 C5 -2(2) . . . . ? C7 O1 C6 C1 -73.2(18) . . . . ? C7 O1 C6 C5 113.3(16) . . . . ? C4 C5 C6 C1 -1(2) . . . . ? F4 C5 C6 C1 -174.0(13) . . . . ? C4 C5 C6 O1 173.0(14) . . . . ? F4 C5 C6 O1 0(2) . . . . ? C6 O1 C7 C13 162.6(13) . . . . ? C6 O1 C7 C8 -76.8(16) . . . . ? C11 N1 C10 C9 0(3) . . . . ? C8 C9 C10 N1 4(3) . . . . ? C10 N1 C11 C12 -5(3) . . . . ? C10 C9 C8 C12 -5(3) . . . . ? C10 C9 C8 C7 170.9(18) . . . . ? O1 C7 C8 C12 142.1(18) . . . . ? C13 C7 C8 C12 -97(2) . . . . ? O1 C7 C8 C9 -34(3) . . . . ? C13 C7 C8 C9 87(2) . . . . ? C9 C8 C12 C11 1(3) . . . . ? C7 C8 C12 C11 -174.8(19) . . . . ? N1 C11 C12 C8 4(3) . . . . ? C19 O2 C13 C7 146.9(14) . . . . ? C19 O2 C13 C14 -99.0(18) . . . . ? O1 C7 C13 O2 56.6(16) . . . . ? C8 C7 C13 O2 -67.5(17) . . . . ? O1 C7 C13 C14 -58.5(17) . . . . ? C8 C7 C13 C14 177.5(14) . . . . ? O2 C13 C14 C15 -21(3) . . . . ? C7 C13 C14 C15 92(2) . . . . ? O2 C13 C14 C18 165.0(19) . . . . ? C7 C13 C14 C18 -82(2) . . . . ? C18 C14 C15 C16 -8(3) . . . . ? C13 C14 C15 C16 177.4(19) . . . . ? C17 N2 C16 C15 -1(3) . . . . ? C14 C15 C16 N2 4(3) . . . . ? C16 N2 C17 C18 4(3) . . . . ? N2 C17 C18 C14 -9(3) . . . . ? C15 C14 C18 C17 11(3) . . . . ? C13 C14 C18 C17 -175(2) . . . . ? C13 O2 C19 C20 27(2) . . . . ? C13 O2 C19 C24 -154.4(14) . . . . ? O2 C19 C20 F5 0(3) . . . . ? C24 C19 C20 F5 -178.9(14) . . . . ? O2 C19 C20 C21 179.8(15) . . . . ? C24 C19 C20 C21 1(2) . . . . ? F5 C20 C21 F6 0(2) . . . . ? C19 C20 C21 F6 -179.4(15) . . . . ? F5 C20 C21 C22 178.9(16) . . . . ? C19 C20 C21 C22 -1(3) . . . . ? F6 C21 C22 C23 179.4(15) . . . . ? C20 C21 C22 C23 1(3) . . . . ? F6 C21 C22 I2 1(2) . . . . ? C20 C21 C22 I2 -178.1(13) . . . . ? C21 C22 C23 F7 -176.6(15) . . . . ? I2 C22 C23 F7 2(2) . . . . ? C21 C22 C23 C24 -1(3) . . . . ? I2 C22 C23 C24 177.9(13) . . . . ? F7 C23 C24 F8 -3(2) . . . . ? C22 C23 C24 F8 -178.4(15) . . . . ? F7 C23 C24 C19 176.9(14) . . . . ? C22 C23 C24 C19 1(3) . . . . ? O2 C19 C24 F8 -1(2) . . . . ? C20 C19 C24 F8 178.5(14) . . . . ? O2 C19 C24 C23 179.8(15) . . . . ? C20 C19 C24 C23 -1(2) . . . . ? C30 C25 C26 C27 0(3) . . . . ? N3B C25 C26 C27 176.7(19) . . . . ? N3A C25 C26 C27 -174.3(16) . . . . ? C25 C26 C27 C28 -2(3) . . . . ? C26 C27 C28 C29 1(3) . . . . ? C27 C28 C29 C30 1(3) . . . . ? C28 C29 C30 C25 -2(3) . . . . ? C26 C25 C30 C29 2(3) . . . . ? N3B C25 C30 C29 -175(2) . . . . ? N3A C25 C30 C29 176.4(17) . . . . ? C26 C25 N3A O3A 168(2) . . . . ? C30 C25 N3A O3A -7(3) . . . . ? N3B C25 N3A O3A -126(4) . . . . ? C26 C25 N3A O4A -30(3) . . . . ? C30 C25 N3A O4A 156(2) . . . . ? N3B C25 N3A O4A 37(3) . . . . ? C26 C25 N3B O3B -166(3) . . . . ? C30 C25 N3B O3B 11(4) . . . . ? N3A C25 N3B O3B 77(5) . . . . ? C26 C25 N3B O4B 24(4) . . . . ? C30 C25 N3B O4B -159(3) . . . . ? N3A C25 N3B O4B -93(4) . . . . ? C36 C31 C32 C33 8(5) . . . . ? N4 C31 C32 C33 173(3) . . . . ? C31 C32 C33 C34 1(5) . . . . ? C32 C33 C34 C35 -6(5) . . . . ? C33 C34 C35 C36 1(6) . . . . ? C34 C35 C36 C31 7(5) . . . . ? C32 C31 C36 C35 -13(5) . . . . ? N4 C31 C36 C35 -177(3) . . . . ? C36 C31 N4 O5 -159(3) . . . . ? C32 C31 N4 O5 35(4) . . . . ? C36 C31 N4 O6 34(4) . . . . ? C32 C31 N4 O6 -132(3) . . . . ? C42 C37 C38 C39 -8(8) . . . . ? N5 C37 C38 C39 -178(5) . . . . ? C37 C38 C39 C40 10(8) . . . . ? C38 C39 C40 C41 -10(10) . . . . ? C39 C40 C41 C42 9(11) . . . . ? C40 C41 C42 C37 -8(11) . . . . ? C38 C37 C42 C41 7(10) . . . . ? N5 C37 C42 C41 177(6) . . . . ? C38 C37 N5 O7 8(8) . . . . ? C42 C37 N5 O7 -163(6) . . . . ? C38 C37 N5 O8 -178(6) . . . . ? C42 C37 N5 O8 12(8) . . . . ? _diffrn_measured_fraction_theta_max 0.671 _diffrn_reflns_theta_full 24.41 _diffrn_measured_fraction_theta_full 0.671 _refine_diff_density_max 1.275 _refine_diff_density_min -1.563 _refine_diff_density_rms 0.189 data_jm062 _database_code_depnum_ccdc_archive 'CCDC 866320' #TrackingRef 'JM062.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H11 N2 O2 F8 I2 1+, 2(C6 H4 Br2), I 1-' _chemical_formula_sum 'C36 H19 Br4 F8 I3 N2 O2' _chemical_formula_weight 1363.87 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 '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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.2497(4) _cell_length_b 11.8502(6) _cell_length_c 19.1570(10) _cell_angle_alpha 92.354(3) _cell_angle_beta 94.750(3) _cell_angle_gamma 98.469(3) _cell_volume 2066.76(17) _cell_formula_units_Z 2 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 9962 _cell_measurement_theta_min 2.56 _cell_measurement_theta_max 31.34 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.192 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1272 _exptl_absorpt_coefficient_mu 6.206 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.' _exptl_absorpt_correction_T_min 0.2764 _exptl_absorpt_correction_T_max 0.3649 _exptl_special_details ; Bruker KRYOFLEX low temperature device. The crystal was not really perfect. In fact a % small amount of reflections were not indexed. They belong to small fragments or were do to a partial twinning. It was impossible to eliminate completely their contribution, as evidenced by relatively high R and wR, but this seems do not affect the result of the structure dtermination. ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_standards_decay_% 0.00 _diffrn_reflns_number 37595 _diffrn_reflns_av_R_equivalents 0.0343 _diffrn_reflns_av_sigmaI/netI 0.0551 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.39 _diffrn_reflns_theta_max 32.65 _reflns_number_total 13288 _reflns_number_gt 9168 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution ; SIR2002 (Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103.) ; _computing_structure_refinement 'SHELXL (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122)' _computing_molecular_graphics ; ORTEP-3 (Farrugia, L.J. (1997) Jour. Appl. Cryst. 30, 565) Mercury (Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457 ; _computing_publication_material SHELXTL _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. The only refined H atom was that bonded to N1, detected directly by the difference map; it was restrained to be on the mean plane of the pyridine C8,C9,C10,N1,C11,C12. One of two molecules of 1,3-dibromobenzene was completely disordered. It was split in three models corresponding to three different sets of halogen bondings. The first two models A,B, roteted 9.0 \% each to the other, were refined assuming equal population factor, while the third, less populated and rotated about 67 \% whit respect to the model A, had occupancy factor 1-occ(A)-occ(B). ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0548P)^2^+21.9718P] 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 ? _refine_ls_number_reflns 13288 _refine_ls_number_parameters 645 _refine_ls_number_restraints 691 _refine_ls_R_factor_all 0.0926 _refine_ls_R_factor_gt 0.0561 _refine_ls_wR_factor_ref 0.1559 _refine_ls_wR_factor_gt 0.1404 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.041 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I1 I 0.40116(4) 0.11010(4) -0.05696(2) 0.02595(9) Uani 1 1 d . . . I2 I -0.35894(5) 0.01849(4) 0.62031(2) 0.02907(10) Uani 1 1 d . . . F1 F 0.2981(4) 0.1894(3) 0.2140(2) 0.0317(9) Uani 1 1 d . . . F2 F 0.4368(4) 0.2376(3) 0.1001(2) 0.0334(9) Uani 1 1 d . . . F3 F 0.1426(4) -0.0796(3) -0.0234(2) 0.0287(8) Uani 1 1 d . . . F4 F 0.0089(4) -0.1304(3) 0.0906(2) 0.0259(8) Uani 1 1 d . . . F5 F -0.2629(5) -0.1831(3) 0.3730(2) 0.0322(9) Uani 1 1 d . . . F6 F -0.3990(5) -0.1743(4) 0.4904(2) 0.0365(10) Uani 1 1 d . . . F7 F 0.0199(5) 0.1748(3) 0.4359(2) 0.0326(9) Uani 1 1 d . . . F8 F -0.1123(5) 0.1851(4) 0.5540(2) 0.0382(10) Uani 1 1 d . . . O1 O 0.0902(4) 0.0083(3) 0.2180(2) 0.0190(8) Uani 1 1 d . . . O2 O -0.0457(4) -0.0109(3) 0.3427(2) 0.0188(8) Uani 1 1 d . . . N1 N -0.0865(6) -0.4003(4) 0.2545(3) 0.0286(12) Uani 1 1 d D . . H1 H -0.108(5) -0.488(8) 0.2613(12) 0.05(3) Uiso 1 1 d D . . N2 N -0.1084(7) 0.3732(5) 0.2577(4) 0.0345(14) Uani 1 1 d . . . C1 C 0.2570(7) 0.1226(5) 0.1552(3) 0.0225(12) Uani 1 1 d . . . C2 C 0.3293(6) 0.1469(5) 0.0960(3) 0.0222(12) Uani 1 1 d . . . C3 C 0.2921(6) 0.0807(5) 0.0343(3) 0.0214(11) Uani 1 1 d . . . C4 C 0.1840(6) -0.0102(5) 0.0349(3) 0.0203(11) Uani 1 1 d . . . C5 C 0.1113(6) -0.0379(5) 0.0939(3) 0.0188(11) Uani 1 1 d . . . C6 C 0.1461(6) 0.0312(5) 0.1559(3) 0.0178(10) Uani 1 1 d . . . C7 C -0.0590(7) -0.0455(6) 0.2183(3) 0.0273(13) Uani 1 1 d D . . H7 H -0.1140 -0.0358 0.1723 0.033 Uiso 1 1 calc R . . C8 C -0.0689(7) -0.1740(5) 0.23146(19) 0.0290(14) Uani 1 1 d D . . C9 C 0.0567(8) -0.2182(6) 0.2564(3) 0.0381(17) Uani 1 1 d D . . H9 H 0.1490 -0.1706 0.2653 0.046 Uiso 1 1 calc R . . C10 C 0.0417(7) -0.3326(5) 0.2674(3) 0.0298(14) Uani 1 1 d D . . H10 H 0.1251 -0.3644 0.2848 0.036 Uiso 1 1 calc R . . C11 C -0.2074(7) -0.3590(5) 0.2310(3) 0.0265(13) Uani 1 1 d D . . H11 H -0.2968 -0.4098 0.2202 0.032 Uiso 1 1 calc R . . C12 C -0.2041(7) -0.2450(5) 0.2222(4) 0.0265(13) Uani 1 1 d . . . H12 H -0.2918 -0.2147 0.2101 0.032 Uiso 1 1 calc R . . C13 C -0.1266(7) 0.0132(6) 0.2769(4) 0.0287(14) Uani 1 1 d . . . H13 H -0.2321 -0.0209 0.2770 0.034 Uiso 1 1 calc R . . C14 C -0.1158(8) 0.1407(6) 0.2681(4) 0.0335(16) Uani 1 1 d . . . C15 C -0.2371(9) 0.1838(6) 0.2360(5) 0.047(2) Uani 1 1 d . . . H15 H -0.3232 0.1342 0.2177 0.056 Uiso 1 1 calc R . . C16 C -0.2265(8) 0.3007(6) 0.2320(5) 0.0392(18) Uani 1 1 d . . . H16 H -0.3072 0.3308 0.2099 0.047 Uiso 1 1 calc R . . C17 C 0.0090(7) 0.3302(5) 0.2843(4) 0.0297(14) Uani 1 1 d . . . H17 H 0.0944 0.3817 0.3014 0.036 Uiso 1 1 calc R . . C18 C 0.0114(7) 0.2146(5) 0.2880(4) 0.0286(14) Uani 1 1 d . . . H18 H 0.0988 0.1867 0.3039 0.034 Uiso 1 1 calc R . . C19 C -0.1213(6) -0.0034(5) 0.4001(3) 0.0205(11) Uani 1 1 d . . . C20 C -0.2291(7) -0.0929(5) 0.4167(3) 0.0216(11) Uani 1 1 d . . . C21 C -0.2975(7) -0.0858(5) 0.4776(3) 0.0238(12) Uani 1 1 d . . . C22 C -0.2608(7) 0.0073(6) 0.5262(3) 0.0261(13) Uani 1 1 d . . . C23 C -0.1563(7) 0.0936(6) 0.5089(3) 0.0261(13) Uani 1 1 d . . . C24 C -0.0858(7) 0.0906(5) 0.4484(3) 0.0217(12) Uani 1 1 d . . . I3 I 0.53797(4) 0.09408(4) -0.21918(2) 0.02372(9) Uani 1 1 d . . . Br1 Br 0.73633(8) 0.35599(6) -0.12319(4) 0.03644(17) Uani 1 1 d . . . Br2 Br 1.34264(8) 0.50351(7) -0.06066(5) 0.04054(18) Uani 1 1 d . . . C25 C 0.8930(7) 0.4778(6) -0.1001(4) 0.0271(13) Uani 1 1 d . . . C26 C 1.0342(8) 0.4507(6) -0.0887(3) 0.0292(14) Uani 1 1 d . . . H26 H 1.0514 0.3736 -0.0912 0.035 Uiso 1 1 calc R . . C27 C 1.1481(8) 0.5394(6) -0.0734(4) 0.0312(14) Uani 1 1 d . . . C28 C 1.1248(8) 0.6516(6) -0.0688(4) 0.0361(16) Uani 1 1 d . . . H28 H 1.2048 0.7116 -0.0582 0.043 Uiso 1 1 calc R . . C29 C 0.9840(9) 0.6752(7) -0.0797(5) 0.0412(18) Uani 1 1 d . . . H29 H 0.9664 0.7522 -0.0762 0.049 Uiso 1 1 calc R . . C30 C 0.8665(9) 0.5871(7) -0.0959(4) 0.0364(16) Uani 1 1 d . . . H30 H 0.7692 0.6037 -0.1039 0.044 Uiso 1 1 calc R . . Br3A Br 0.1578(5) 0.4044(4) -0.4988(3) 0.214(4) Uani 0.4090(14) 1 d PDU A 1 Br4A Br 0.5869(3) 0.4933(6) -0.2728(3) 0.097(2) Uani 0.4090(14) 1 d PDU A 1 C31A C 0.4711(4) 0.5486(8) -0.3432(3) 0.081(5) Uani 0.4090(14) 1 d PDU A 1 C32A C 0.3739(5) 0.4713(9) -0.3876(3) 0.084(5) Uani 0.4090(14) 1 d PDU A 1 H32A H 0.3678 0.3917 -0.3815 0.101 Uiso 0.4090(14) 1 calc PR A 1 C33A C 0.2855(6) 0.5103(9) -0.4410(4) 0.084(5) Uani 0.4090(14) 1 d PDU A 1 C34A C 0.2944(8) 0.6268(8) -0.4500(5) 0.084(5) Uani 0.4090(14) 1 d PDU A 1 H34A H 0.2342 0.6537 -0.4864 0.101 Uiso 0.4090(14) 1 calc PR A 1 C35A C 0.3915(9) 0.7040(9) -0.4056(5) 0.080(6) Uani 0.4090(14) 1 d PDU A 1 H35A H 0.3976 0.7837 -0.4117 0.096 Uiso 0.4090(14) 1 calc PR A 1 C36A C 0.4799(9) 0.6650(9) -0.3522(5) 0.079(6) Uani 0.4090(14) 1 d PDU A 1 H36A H 0.5461 0.7179 -0.3220 0.095 Uiso 0.4090(14) 1 calc PR A 1 Br3B Br 0.2042(4) 0.4126(3) -0.52303(17) 0.0634(9) Uani 0.4090(14) 1 d PDU A 2 Br4B Br 0.5866(2) 0.5050(4) -0.27263(14) 0.0374(7) Uani 0.4090(14) 1 d PDU A 2 C31B C 0.4724(3) 0.5546(6) -0.3489(3) 0.022(3) Uani 0.4090(14) 1 d PDU A 2 C32B C 0.3939(4) 0.4759(7) -0.3992(3) 0.026(3) Uani 0.4090(14) 1 d PDU A 2 H32B H 0.3966 0.3964 -0.3959 0.031 Uiso 0.4090(14) 1 calc PR A 2 C33B C 0.3115(5) 0.5156(7) -0.4543(3) 0.026(3) Uani 0.4090(14) 1 d PDU A 2 C34B C 0.3064(6) 0.6315(6) -0.4598(4) 0.030(3) Uani 0.4090(14) 1 d PDU A 2 H34B H 0.2497 0.6576 -0.4978 0.036 Uiso 0.4090(14) 1 calc PR A 2 C35B C 0.3854(7) 0.7087(7) -0.4091(4) 0.024(3) Uani 0.4090(14) 1 d PDU A 2 H35B H 0.3826 0.7882 -0.4124 0.029 Uiso 0.4090(14) 1 calc PR A 2 C36B C 0.4688(7) 0.6708(7) -0.3535(4) 0.022(3) Uani 0.4090(14) 1 d PDU A 2 H36B H 0.5228 0.7240 -0.3190 0.027 Uiso 0.4090(14) 1 calc PR A 2 Br4C Br 0.5709(3) 0.3584(8) -0.3133(5) 0.124(4) Uani 0.182(3) 1 d PD A 3 Br3C Br 0.7856(8) 0.4217(14) -0.5776(6) 0.250(12) Uani 0.182(3) 1 d PDU A 3 C31C C 0.6183(4) 0.4521(9) -0.3860(4) 0.103(7) Uani 0.182(3) 1 d PDU A 3 C32C C 0.6748(5) 0.4088(9) -0.4448(4) 0.100(7) Uani 0.182(3) 1 d PDU A 3 H32C H 0.6894 0.3311 -0.4479 0.120 Uiso 0.182(3) 1 calc PR A 3 C33C C 0.7100(6) 0.4795(10) -0.4990(5) 0.100(7) Uani 0.182(3) 1 d PDU A 3 C34C C 0.6887(8) 0.5932(10) -0.4945(6) 0.101(7) Uani 0.182(3) 1 d PDU A 3 H34C H 0.7128 0.6414 -0.5315 0.121 Uiso 0.182(3) 1 calc PR A 3 C35C C 0.6322(9) 0.6363(10) -0.4357(6) 0.104(7) Uani 0.182(3) 1 d PDU A 3 H35C H 0.6177 0.7139 -0.4325 0.125 Uiso 0.182(3) 1 calc PR A 3 C36C C 0.5970(8) 0.5658(9) -0.3814(6) 0.104(7) Uani 0.182(3) 1 d PDU A 3 H36C H 0.5584 0.5953 -0.3412 0.125 Uiso 0.182(3) 1 calc PR A 3 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 0.02096(18) 0.0334(2) 0.02631(19) 0.01229(16) 0.00753(14) 0.00747(15) I2 0.02390(19) 0.0425(3) 0.02221(19) 0.00213(17) 0.00450(15) 0.00817(17) F1 0.035(2) 0.026(2) 0.0287(19) -0.0064(15) 0.0066(16) -0.0106(16) F2 0.030(2) 0.026(2) 0.041(2) 0.0049(17) 0.0078(17) -0.0110(16) F3 0.0307(19) 0.028(2) 0.0266(19) -0.0032(15) 0.0018(15) 0.0030(16) F4 0.0247(17) 0.0169(17) 0.0330(19) 0.0003(14) 0.0042(15) -0.0073(14) F5 0.043(2) 0.0203(18) 0.031(2) -0.0001(15) 0.0053(17) -0.0054(16) F6 0.038(2) 0.037(2) 0.031(2) 0.0048(17) 0.0091(17) -0.0122(18) F7 0.038(2) 0.0231(19) 0.034(2) 0.0007(16) 0.0058(17) -0.0030(16) F8 0.051(3) 0.031(2) 0.032(2) -0.0072(17) 0.0049(19) 0.0072(19) O1 0.0170(18) 0.0196(19) 0.0206(19) 0.0057(15) 0.0055(15) 0.0003(15) O2 0.0196(19) 0.0164(19) 0.0204(19) 0.0025(15) 0.0022(15) 0.0019(15) N1 0.036(3) 0.014(2) 0.037(3) 0.005(2) 0.005(2) 0.006(2) N2 0.036(3) 0.014(2) 0.054(4) 0.007(2) 0.005(3) 0.004(2) C1 0.023(3) 0.018(3) 0.026(3) -0.001(2) 0.003(2) 0.001(2) C2 0.021(3) 0.015(3) 0.030(3) 0.011(2) 0.002(2) -0.002(2) C3 0.021(3) 0.025(3) 0.021(3) 0.008(2) 0.007(2) 0.010(2) C4 0.018(2) 0.019(3) 0.025(3) 0.002(2) 0.005(2) 0.006(2) C5 0.018(2) 0.015(2) 0.024(3) 0.006(2) 0.002(2) 0.001(2) C6 0.016(2) 0.015(2) 0.024(3) 0.005(2) 0.007(2) 0.0023(19) C7 0.021(3) 0.028(3) 0.032(3) 0.006(3) 0.004(2) 0.001(2) C8 0.029(3) 0.016(3) 0.042(4) 0.002(3) 0.000(3) 0.002(2) C9 0.028(3) 0.025(3) 0.059(5) 0.002(3) -0.009(3) 0.004(3) C10 0.026(3) 0.020(3) 0.045(4) 0.006(3) -0.001(3) 0.008(2) C11 0.025(3) 0.020(3) 0.035(3) 0.004(2) 0.006(3) 0.003(2) C12 0.026(3) 0.022(3) 0.033(3) 0.000(2) 0.002(3) 0.007(2) C13 0.021(3) 0.033(3) 0.032(3) 0.004(3) 0.003(2) 0.003(3) C14 0.031(3) 0.018(3) 0.052(4) 0.004(3) -0.003(3) 0.008(3) C15 0.033(4) 0.016(3) 0.089(7) 0.003(4) -0.016(4) 0.005(3) C16 0.028(3) 0.024(3) 0.067(5) 0.019(3) 0.000(3) 0.005(3) C17 0.027(3) 0.019(3) 0.041(4) 0.007(3) 0.002(3) -0.004(2) C18 0.028(3) 0.017(3) 0.041(4) 0.001(3) -0.001(3) 0.004(2) C19 0.019(2) 0.024(3) 0.021(3) 0.004(2) 0.002(2) 0.006(2) C20 0.027(3) 0.020(3) 0.018(3) 0.001(2) 0.001(2) 0.003(2) C21 0.023(3) 0.024(3) 0.023(3) 0.007(2) -0.001(2) 0.000(2) C22 0.026(3) 0.033(3) 0.021(3) 0.003(2) 0.001(2) 0.010(3) C23 0.029(3) 0.027(3) 0.024(3) -0.001(2) 0.001(2) 0.009(2) C24 0.023(3) 0.017(3) 0.026(3) 0.000(2) 0.001(2) 0.003(2) I3 0.01641(16) 0.0326(2) 0.02314(18) 0.00196(15) 0.00331(13) 0.00596(14) Br1 0.0304(3) 0.0294(4) 0.0453(4) -0.0039(3) -0.0037(3) -0.0038(3) Br2 0.0246(3) 0.0432(4) 0.0536(5) 0.0030(4) 0.0033(3) 0.0045(3) C25 0.025(3) 0.024(3) 0.031(3) -0.002(2) -0.002(2) 0.000(2) C26 0.035(3) 0.026(3) 0.025(3) 0.000(2) 0.002(3) 0.004(3) C27 0.026(3) 0.033(4) 0.034(3) 0.007(3) 0.000(3) 0.004(3) C28 0.034(4) 0.027(3) 0.044(4) 0.006(3) 0.001(3) -0.006(3) C29 0.039(4) 0.029(4) 0.054(5) 0.006(3) -0.008(4) 0.005(3) C30 0.036(4) 0.033(4) 0.040(4) 0.003(3) -0.002(3) 0.007(3) Br3A 0.175(5) 0.044(2) 0.377(10) -0.026(4) -0.207(6) 0.006(3) Br4A 0.055(3) 0.117(4) 0.124(4) 0.079(3) 0.007(3) 0.009(3) C31A 0.058(9) 0.089(10) 0.092(10) 0.010(9) -0.004(8) 0.000(9) C32A 0.063(9) 0.084(10) 0.099(10) 0.013(9) -0.011(8) -0.001(9) C33A 0.064(9) 0.087(10) 0.094(10) 0.006(9) -0.010(8) 0.003(9) C34A 0.065(9) 0.090(10) 0.091(10) 0.003(9) -0.004(9) -0.002(9) C35A 0.066(9) 0.084(10) 0.085(10) 0.007(9) 0.003(9) -0.002(9) C36A 0.060(9) 0.087(10) 0.084(10) 0.003(9) 0.002(9) -0.005(9) Br3B 0.0678(18) 0.0476(17) 0.0643(16) -0.0300(13) -0.0144(15) -0.0050(13) Br4B 0.0196(13) 0.0486(16) 0.0418(15) 0.0194(13) -0.0069(11) -0.0011(11) C31B 0.019(5) 0.019(5) 0.027(5) 0.015(5) -0.001(5) -0.006(4) C32B 0.027(5) 0.009(5) 0.040(6) 0.012(5) -0.001(5) -0.003(4) C33B 0.030(6) 0.013(5) 0.032(6) -0.004(5) -0.002(5) -0.005(5) C34B 0.036(6) 0.015(5) 0.036(6) -0.002(5) -0.004(5) -0.004(5) C35B 0.035(6) 0.008(5) 0.027(6) 0.002(5) -0.001(5) -0.005(5) C36B 0.024(5) 0.016(5) 0.022(5) 0.001(5) -0.001(5) -0.009(5) Br4C 0.034(3) 0.098(6) 0.244(13) 0.038(7) 0.025(5) 0.005(3) Br3C 0.108(10) 0.211(19) 0.43(3) -0.06(2) 0.038(15) 0.042(11) C31C 0.063(11) 0.077(11) 0.166(12) 0.018(11) 0.036(11) -0.013(11) C32C 0.058(11) 0.076(11) 0.165(12) 0.019(11) 0.039(11) -0.016(10) C33C 0.058(11) 0.074(11) 0.167(12) 0.017(11) 0.042(11) -0.013(11) C34C 0.060(11) 0.075(11) 0.168(12) 0.015(12) 0.039(11) -0.012(11) C35C 0.065(11) 0.077(11) 0.168(12) 0.015(12) 0.035(11) -0.011(11) C36C 0.066(11) 0.077(12) 0.167(13) 0.017(12) 0.034(11) -0.013(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I1 C3 2.105(6) . ? I2 C22 2.093(6) . ? F1 C1 1.345(7) . ? F2 C2 1.347(7) . ? F3 C4 1.354(7) . ? F4 C5 1.334(6) . ? F5 C20 1.315(7) . ? F6 C21 1.345(7) . ? F7 C24 1.334(7) . ? F8 C23 1.350(8) . ? O1 C6 1.358(7) . ? O1 C7 1.433(7) . ? O2 C19 1.358(7) . ? O2 C13 1.472(8) . ? N1 C10 1.329(9) . ? N1 C11 1.337(9) . ? N1 H1 1.04(9) . ? N2 C16 1.332(10) . ? N2 C17 1.338(9) . ? C1 C6 1.379(8) . ? C1 C2 1.382(8) . ? C2 C3 1.382(9) . ? C3 C4 1.359(8) . ? C4 C5 1.389(8) . ? C5 C6 1.401(8) . ? C7 C13 1.522(9) . ? C7 C8 1.544(9) . ? C7 H7 1.0000 . ? C8 C12 1.394(9) . ? C8 C9 1.401(9) . ? C9 C10 1.369(10) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C11 C12 1.365(9) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C14 1.516(10) . ? C13 H13 1.0000 . ? C14 C18 1.376(10) . ? C14 C15 1.406(10) . ? C15 C16 1.380(10) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 C18 1.378(9) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? C19 C24 1.401(8) . ? C19 C20 1.410(8) . ? C20 C21 1.377(8) . ? C21 C22 1.398(9) . ? C22 C23 1.370(10) . ? C23 C24 1.378(9) . ? Br1 C25 1.898(6) . ? Br2 C27 1.908(7) . ? C25 C30 1.353(10) . ? C25 C26 1.393(10) . ? C26 C27 1.378(10) . ? C26 H26 0.9500 . ? C27 C28 1.379(11) . ? C28 C29 1.373(11) . ? C28 H28 0.9500 . ? C29 C30 1.397(11) . ? C29 H29 0.9500 . ? C30 H30 0.9500 . ? Br3A C33A 1.852(9) . ? Br4A C31A 1.854(8) . ? C31A C36A 1.388(7) . ? C31A C32A 1.392(6) . ? C32A C33A 1.392(7) . ? C32A H32A 0.9500 . ? C33A C34A 1.389(7) . ? C34A C35A 1.391(7) . ? C34A H34A 0.9500 . ? C35A C36A 1.392(7) . ? C35A H35A 0.9500 . ? C36A H36A 0.9500 . ? Br3B C33B 1.872(7) . ? Br4B C31B 1.895(6) . ? C31B C36B 1.389(7) . ? C31B C32B 1.391(6) . ? C32B C33B 1.388(6) . ? C32B H32B 0.9500 . ? C33B C34B 1.390(7) . ? C34B C35B 1.388(6) . ? C34B H34B 0.9500 . ? C35B C36B 1.392(7) . ? C35B H35B 0.9500 . ? C36B H36B 0.9500 . ? Br4C C31C 1.856(10) . ? Br3C C33C 1.859(11) . ? C31C C32C 1.391(7) . ? C31C C36C 1.391(7) . ? C32C C33C 1.391(7) . ? C32C H32C 0.9500 . ? C33C C34C 1.390(7) . ? C34C C35C 1.390(7) . ? C34C H34C 0.9500 . ? C35C C36C 1.389(7) . ? C35C H35C 0.9500 . ? C36C H36C 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 O1 C7 119.4(4) . . ? C19 O2 C13 113.9(4) . . ? C10 N1 C11 121.3(6) . . ? C10 N1 H1 127(3) . . ? C11 N1 H1 112(3) . . ? C16 N2 C17 118.3(6) . . ? F1 C1 C6 119.3(5) . . ? F1 C1 C2 118.7(5) . . ? C6 C1 C2 122.1(6) . . ? F2 C2 C3 120.8(5) . . ? F2 C2 C1 118.1(6) . . ? C3 C2 C1 121.1(5) . . ? C4 C3 C2 117.1(5) . . ? C4 C3 I1 119.7(4) . . ? C2 C3 I1 123.2(4) . . ? F3 C4 C3 120.4(5) . . ? F3 C4 C5 116.5(5) . . ? C3 C4 C5 123.1(6) . . ? F4 C5 C4 119.3(5) . . ? F4 C5 C6 121.0(5) . . ? C4 C5 C6 119.8(5) . . ? O1 C6 C1 117.7(5) . . ? O1 C6 C5 125.0(5) . . ? C1 C6 C5 116.9(5) . . ? O1 C7 C13 107.8(5) . . ? O1 C7 C8 111.6(5) . . ? C13 C7 C8 109.0(4) . . ? O1 C7 H7 109.5 . . ? C13 C7 H7 109.5 . . ? C8 C7 H7 109.5 . . ? C12 C8 C9 119.8(6) . . ? C12 C8 C7 120.2(6) . . ? C9 C8 C7 119.9(6) . . ? C10 C9 C8 117.6(6) . . ? C10 C9 H9 121.2 . . ? C8 C9 H9 121.2 . . ? N1 C10 C9 121.8(6) . . ? N1 C10 H10 119.1 . . ? C9 C10 H10 119.1 . . ? N1 C11 C12 120.8(6) . . ? N1 C11 H11 119.6 . . ? C12 C11 H11 119.6 . . ? C11 C12 C8 118.4(6) . . ? C11 C12 H12 120.8 . . ? C8 C12 H12 120.8 . . ? O2 C13 C14 111.4(5) . . ? O2 C13 C7 106.0(5) . . ? C14 C13 C7 111.5(6) . . ? O2 C13 H13 109.3 . . ? C14 C13 H13 109.3 . . ? C7 C13 H13 109.3 . . ? C18 C14 C15 119.1(6) . . ? C18 C14 C13 121.7(6) . . ? C15 C14 C13 119.1(6) . . ? C16 C15 C14 117.7(7) . . ? C16 C15 H15 121.2 . . ? C14 C15 H15 121.2 . . ? N2 C16 C15 123.0(7) . . ? N2 C16 H16 118.5 . . ? C15 C16 H16 118.5 . . ? N2 C17 C18 122.9(6) . . ? N2 C17 H17 118.5 . . ? C18 C17 H17 118.5 . . ? C14 C18 C17 118.4(6) . . ? C14 C18 H18 120.8 . . ? C17 C18 H18 120.8 . . ? O2 C19 C24 120.6(5) . . ? O2 C19 C20 121.9(5) . . ? C24 C19 C20 117.3(5) . . ? F5 C20 C21 120.7(5) . . ? F5 C20 C19 118.7(5) . . ? C21 C20 C19 120.6(6) . . ? F6 C21 C20 117.7(6) . . ? F6 C21 C22 120.3(6) . . ? C20 C21 C22 122.0(6) . . ? C23 C22 C21 116.4(6) . . ? C23 C22 I2 120.7(5) . . ? C21 C22 I2 122.9(5) . . ? F8 C23 C22 119.8(6) . . ? F8 C23 C24 116.6(6) . . ? C22 C23 C24 123.5(6) . . ? F7 C24 C23 120.9(5) . . ? F7 C24 C19 119.0(5) . . ? C23 C24 C19 120.1(6) . . ? C30 C25 C26 121.8(6) . . ? C30 C25 Br1 120.3(5) . . ? C26 C25 Br1 117.8(5) . . ? C27 C26 C25 117.7(6) . . ? C27 C26 H26 121.1 . . ? C25 C26 H26 121.1 . . ? C26 C27 C28 121.8(7) . . ? C26 C27 Br2 118.1(5) . . ? C28 C27 Br2 120.1(5) . . ? C29 C28 C27 118.9(7) . . ? C29 C28 H28 120.6 . . ? C27 C28 H28 120.6 . . ? C28 C29 C30 120.5(7) . . ? C28 C29 H29 119.7 . . ? C30 C29 H29 119.7 . . ? C25 C30 C29 119.1(7) . . ? C25 C30 H30 120.4 . . ? C29 C30 H30 120.4 . . ? C36A C31A C32A 119.8(6) . . ? C36A C31A Br4A 121.2(5) . . ? C32A C31A Br4A 119.0(6) . . ? C33A C32A C31A 120.3(6) . . ? C33A C32A H32A 119.9 . . ? C31A C32A H32A 119.9 . . ? C34A C33A C32A 119.9(6) . . ? C34A C33A Br3A 121.4(5) . . ? C32A C33A Br3A 118.7(6) . . ? C33A C34A C35A 119.8(7) . . ? C33A C34A H34A 120.1 . . ? C35A C34A H34A 120.1 . . ? C34A C35A C36A 120.2(7) . . ? C34A C35A H35A 119.9 . . ? C36A C35A H35A 119.9 . . ? C31A C36A C35A 119.9(7) . . ? C31A C36A H36A 120.0 . . ? C35A C36A H36A 120.0 . . ? C36B C31B C32B 120.8(5) . . ? C36B C31B Br4B 118.6(4) . . ? C32B C31B Br4B 120.5(5) . . ? C33B C32B C31B 118.8(6) . . ? C33B C32B H32B 120.6 . . ? C31B C32B H32B 120.6 . . ? C32B C33B C34B 121.3(6) . . ? C32B C33B Br3B 120.2(5) . . ? C34B C33B Br3B 118.5(5) . . ? C35B C34B C33B 119.1(6) . . ? C35B C34B H34B 120.5 . . ? C33B C34B H34B 120.5 . . ? C34B C35B C36B 120.6(6) . . ? C34B C35B H35B 119.7 . . ? C36B C35B H35B 119.7 . . ? C31B C36B C35B 119.4(6) . . ? C31B C36B H36B 120.3 . . ? C35B C36B H36B 120.3 . . ? C32C C31C C36C 120.1(7) . . ? C32C C31C Br4C 120.2(6) . . ? C36C C31C Br4C 119.7(6) . . ? C31C C32C C33C 119.9(7) . . ? C31C C32C H32C 120.1 . . ? C33C C32C H32C 120.1 . . ? C34C C33C C32C 120.1(7) . . ? C34C C33C Br3C 120.0(7) . . ? C32C C33C Br3C 119.9(7) . . ? C35C C34C C33C 120.0(7) . . ? C35C C34C H34C 120.0 . . ? C33C C34C H34C 120.0 . . ? C36C C35C C34C 120.1(7) . . ? C36C C35C H35C 120.0 . . ? C34C C35C H35C 120.0 . . ? C35C C36C C31C 120.0(7) . . ? C35C C36C H36C 120.0 . . ? C31C C36C H36C 120.0 . . ? 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 F1 C1 C2 F2 -0.7(9) . . . . ? C6 C1 C2 F2 -179.7(5) . . . . ? F1 C1 C2 C3 179.7(5) . . . . ? C6 C1 C2 C3 0.7(9) . . . . ? F2 C2 C3 C4 179.0(5) . . . . ? C1 C2 C3 C4 -1.3(9) . . . . ? F2 C2 C3 I1 2.0(8) . . . . ? C1 C2 C3 I1 -178.3(5) . . . . ? C2 C3 C4 F3 -179.3(5) . . . . ? I1 C3 C4 F3 -2.3(8) . . . . ? C2 C3 C4 C5 0.1(9) . . . . ? I1 C3 C4 C5 177.2(4) . . . . ? F3 C4 C5 F4 1.2(8) . . . . ? C3 C4 C5 F4 -178.3(5) . . . . ? F3 C4 C5 C6 -178.8(5) . . . . ? C3 C4 C5 C6 1.7(9) . . . . ? C7 O1 C6 C1 151.6(5) . . . . ? C7 O1 C6 C5 -35.7(8) . . . . ? F1 C1 C6 O1 -4.5(8) . . . . ? C2 C1 C6 O1 174.5(5) . . . . ? F1 C1 C6 C5 -177.8(5) . . . . ? C2 C1 C6 C5 1.2(9) . . . . ? F4 C5 C6 O1 5.0(9) . . . . ? C4 C5 C6 O1 -175.1(5) . . . . ? F4 C5 C6 C1 177.7(5) . . . . ? C4 C5 C6 C1 -2.3(8) . . . . ? C6 O1 C7 C13 -138.2(5) . . . . ? C6 O1 C7 C8 102.2(5) . . . . ? O1 C7 C8 C12 -169.4(5) . . . . ? C13 C7 C8 C12 71.7(5) . . . . ? O1 C7 C8 C9 14.0(4) . . . . ? C13 C7 C8 C9 -104.9(5) . . . . ? C12 C8 C9 C10 3.2(5) . . . . ? C7 C8 C9 C10 179.8(2) . . . . ? C11 N1 C10 C9 -1.0(6) . . . . ? C8 C9 C10 N1 0.7(5) . . . . ? C10 N1 C11 C12 -2.7(7) . . . . ? N1 C11 C12 C8 6.4(9) . . . . ? C9 C8 C12 C11 -6.6(8) . . . . ? C7 C8 C12 C11 176.8(4) . . . . ? C19 O2 C13 C14 81.7(6) . . . . ? C19 O2 C13 C7 -156.8(5) . . . . ? O1 C7 C13 O2 -64.4(6) . . . . ? C8 C7 C13 O2 56.9(6) . . . . ? O1 C7 C13 C14 56.9(7) . . . . ? C8 C7 C13 C14 178.2(5) . . . . ? O2 C13 C14 C18 38.0(9) . . . . ? C7 C13 C14 C18 -80.2(9) . . . . ? O2 C13 C14 C15 -144.8(7) . . . . ? C7 C13 C14 C15 97.1(9) . . . . ? C18 C14 C15 C16 -5.9(13) . . . . ? C13 C14 C15 C16 176.7(8) . . . . ? C17 N2 C16 C15 4.7(13) . . . . ? C14 C15 C16 N2 -0.8(15) . . . . ? C16 N2 C17 C18 -1.9(12) . . . . ? C15 C14 C18 C17 8.6(12) . . . . ? C13 C14 C18 C17 -174.2(7) . . . . ? N2 C17 C18 C14 -4.8(12) . . . . ? C13 O2 C19 C24 -105.1(6) . . . . ? C13 O2 C19 C20 80.4(7) . . . . ? O2 C19 C20 F5 -4.1(9) . . . . ? C24 C19 C20 F5 -178.8(5) . . . . ? O2 C19 C20 C21 175.9(5) . . . . ? C24 C19 C20 C21 1.2(9) . . . . ? F5 C20 C21 F6 0.3(9) . . . . ? C19 C20 C21 F6 -179.8(5) . . . . ? F5 C20 C21 C22 178.0(6) . . . . ? C19 C20 C21 C22 -2.1(9) . . . . ? F6 C21 C22 C23 179.9(6) . . . . ? C20 C21 C22 C23 2.3(9) . . . . ? F6 C21 C22 I2 -0.7(8) . . . . ? C20 C21 C22 I2 -178.4(5) . . . . ? C21 C22 C23 F8 -178.3(6) . . . . ? I2 C22 C23 F8 2.3(8) . . . . ? C21 C22 C23 C24 -1.8(10) . . . . ? I2 C22 C23 C24 178.8(5) . . . . ? F8 C23 C24 F7 -0.2(9) . . . . ? C22 C23 C24 F7 -176.9(6) . . . . ? F8 C23 C24 C19 177.7(5) . . . . ? C22 C23 C24 C19 1.1(10) . . . . ? O2 C19 C24 F7 2.5(9) . . . . ? C20 C19 C24 F7 177.3(5) . . . . ? O2 C19 C24 C23 -175.5(6) . . . . ? C20 C19 C24 C23 -0.7(9) . . . . ? C30 C25 C26 C27 -0.7(10) . . . . ? Br1 C25 C26 C27 178.6(5) . . . . ? C25 C26 C27 C28 0.7(11) . . . . ? C25 C26 C27 Br2 -178.0(5) . . . . ? C26 C27 C28 C29 -0.1(12) . . . . ? Br2 C27 C28 C29 178.6(6) . . . . ? C27 C28 C29 C30 -0.6(12) . . . . ? C26 C25 C30 C29 0.1(12) . . . . ? Br1 C25 C30 C29 -179.2(6) . . . . ? C28 C29 C30 C25 0.6(13) . . . . ? C36A C31A C32A C33A 0.0(2) . . . . ? Br4A C31A C32A C33A 180.00(13) . . . . ? C31A C32A C33A C34A 0.0(3) . . . . ? C31A C32A C33A Br3A -179.99(11) . . . . ? C32A C33A C34A C35A 0.0(3) . . . . ? Br3A C33A C34A C35A 179.99(14) . . . . ? C33A C34A C35A C36A 0.0(3) . . . . ? C32A C31A C36A C35A 0.0(2) . . . . ? Br4A C31A C36A C35A -179.99(12) . . . . ? C34A C35A C36A C31A 0.0(3) . . . . ? C36B C31B C32B C33B 0.0(2) . . . . ? Br4B C31B C32B C33B 179.99(12) . . . . ? C31B C32B C33B C34B 0.0(3) . . . . ? C31B C32B C33B Br3B -179.97(11) . . . . ? C32B C33B C34B C35B 0.0(3) . . . . ? Br3B C33B C34B C35B 179.96(14) . . . . ? C33B C34B C35B C36B 0.1(3) . . . . ? C32B C31B C36B C35B 0.1(2) . . . . ? Br4B C31B C36B C35B -179.96(13) . . . . ? C34B C35B C36B C31B -0.1(3) . . . . ? C36C C31C C32C C33C 0.0(2) . . . . ? Br4C C31C C32C C33C 180.00(13) . . . . ? C31C C32C C33C C34C 0.0(3) . . . . ? C31C C32C C33C Br3C -179.99(11) . . . . ? C32C C33C C34C C35C 0.0(3) . . . . ? Br3C C33C C34C C35C 179.99(15) . . . . ? C33C C34C C35C C36C 0.0(3) . . . . ? C34C C35C C36C C31C 0.0(3) . . . . ? C32C C31C C36C C35C 0.0(2) . . . . ? Br4C C31C C36C C35C 180.00(13) . . . . ? _diffrn_measured_fraction_theta_max 0.879 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 3.454 _refine_diff_density_min -1.941 _refine_diff_density_rms 0.214 data_lc63 _database_code_depnum_ccdc_archive 'CCDC 866321' #TrackingRef 'lc63.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H10 F8 I2 N2 O2' _chemical_formula_sum 'C24 H10 F8 I2 N2 O2' _chemical_formula_weight 764.14 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.3175(6) _cell_length_b 10.3237(6) _cell_length_c 13.5796(7) _cell_angle_alpha 68.372(2) _cell_angle_beta 74.546(3) _cell_angle_gamma 85.996(3) _cell_volume 1169.78(12) _cell_formula_units_Z 2 _cell_measurement_temperature 103(2) _cell_measurement_reflns_used 4403 _cell_measurement_theta_min 3.15 _cell_measurement_theta_max 27.64 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.169 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 724 _exptl_absorpt_coefficient_mu 2.780 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Bruker (2001). TWINABS. Bruker AXS Inc., Madison, Wisconsin, USA.' _exptl_absorpt_correction_T_min 0.6037 _exptl_absorpt_correction_T_max 0.7458 _exptl_special_details ; The crystals of lc63 were obtained in a failed attempt to cocrystalize the present molecule with a cobalt salt, following this procedure: lc63 was dissolved in 1 ml of dimethylformamide over which was stratified a methanol/water solution of [Co(ethylendiamine)2Cl2]Cl. After one day apparently perfect, colourless and well faceted crystals were obtained. The same polymorph was obtained by slow evaporation of a acetylacetate solution. All crystal were small pseudo-hexagonal prisms. They estinguish in different triangular zones showing clear twinning. In spite of several attempts, we were not able to cut a single crystal. At the end we decided to collect data on a crystal with two domains clearly distinguishable. Data reduction did not give problems but the solution of the structure was very difficult and was obtained only in the space group P1. After the refinement it was evident that the structure was centric and the final refinement was in P-1. ; _diffrn_ambient_temperature 103(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_standards_decay_% 0.00 _diffrn_reflns_number 36446 _diffrn_reflns_av_R_equivalents 0.0325 _diffrn_reflns_av_sigmaI/netI 0.0253 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 28.67 _reflns_number_total 5060 _reflns_number_gt 4438 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution ; SIR2002 (Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103.) ; _computing_structure_refinement 'SHELXL (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122)' _computing_molecular_graphics ; ORTEP-3 (Farrugia, L.J. (1997) Jour. Appl. Cryst. 30, 565) Mercury (Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457 ; _computing_publication_material SHELXTL _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 'w=1/[\s^2^(Fo^2^)+(0.0950P)^2^+1.4625P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5060 _refine_ls_number_parameters 343 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0536 _refine_ls_R_factor_gt 0.0468 _refine_ls_wR_factor_ref 0.1299 _refine_ls_wR_factor_gt 0.1232 _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_restrained_S_all 1.014 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I1 I 0.27265(4) 0.48786(4) -0.13248(3) 0.03050(13) Uani 1 1 d . . . I2 I 0.24043(4) 1.00259(4) 0.72823(3) 0.03143(13) Uani 1 1 d . . . F1 F 0.3590(4) 1.0788(4) 0.2989(3) 0.0377(8) Uani 1 1 d . . . F2 F 0.3944(5) 1.1333(4) 0.4694(3) 0.0416(9) Uani 1 1 d . . . F3 F 0.0132(4) 0.7978(4) 0.7072(3) 0.0381(8) Uani 1 1 d . . . F4 F -0.0137(4) 0.7373(3) 0.5381(3) 0.0347(8) Uani 1 1 d . . . F5 F 0.0153(4) 0.7431(3) 0.1479(3) 0.0307(7) Uani 1 1 d . . . F6 F 0.0602(4) 0.6915(4) -0.0366(3) 0.0341(8) Uani 1 1 d . . . F7 F 0.3952(5) 0.3406(4) 0.0848(3) 0.0451(10) Uani 1 1 d . . . F8 F 0.3455(4) 0.3915(4) 0.2722(3) 0.0354(8) Uani 1 1 d . . . O1 O 0.1625(4) 0.8684(4) 0.3299(3) 0.0239(8) Uani 1 1 d . . . O2 O 0.1655(4) 0.6067(4) 0.3030(3) 0.0240(8) Uani 1 1 d . . . N1 N 0.2990(6) 1.0061(5) -0.0750(4) 0.0322(11) Uani 1 1 d . . . N2 N 0.3129(6) 0.4929(5) 0.6510(4) 0.0315(11) Uani 1 1 d . . . C1 C 0.2768(7) 1.0072(6) 0.3991(5) 0.0261(12) Uani 1 1 d . . . C2 C 0.2929(7) 1.0344(6) 0.4881(5) 0.0291(12) Uani 1 1 d . . . C3 C 0.2076(6) 0.9665(6) 0.5933(4) 0.0244(11) Uani 1 1 d . . . C4 C 0.1030(6) 0.8675(6) 0.6071(4) 0.0248(11) Uani 1 1 d . . . C5 C 0.0892(6) 0.8357(6) 0.5195(4) 0.0242(11) Uani 1 1 d . . . C6 C 0.1775(6) 0.9020(5) 0.4146(4) 0.0222(10) Uani 1 1 d . . . C7 C 0.2949(6) 0.8242(5) 0.2675(4) 0.0204(10) Uani 1 1 d . . . H7 H 0.3845 0.8611 0.2774 0.024 Uiso 1 1 calc R . . C8 C 0.2952(6) 0.8884(5) 0.1470(4) 0.0215(10) Uani 1 1 d . . . C9 C 0.2045(7) 0.9995(6) 0.1086(5) 0.0275(12) Uani 1 1 d . . . H9 H 0.1397 1.0376 0.1573 0.033 Uiso 1 1 calc R . . C10 C 0.2119(8) 1.0522(6) -0.0025(5) 0.0347(14) Uani 1 1 d . . . H10 H 0.1495 1.1271 -0.0279 0.042 Uiso 1 1 calc R . . C11 C 0.3880(7) 0.9019(6) -0.0386(4) 0.0292(12) Uani 1 1 d . . . H11 H 0.4521 0.8676 -0.0902 0.035 Uiso 1 1 calc R . . C12 C 0.3917(6) 0.8415(5) 0.0699(4) 0.0237(11) Uani 1 1 d . . . H12 H 0.4587 0.7694 0.0917 0.028 Uiso 1 1 calc R . . C13 C 0.2972(6) 0.6640(5) 0.3119(4) 0.0196(10) Uani 1 1 d . . . H13 H 0.3874 0.6342 0.2671 0.023 Uiso 1 1 calc R . . C14 C 0.3014(6) 0.6047(5) 0.4309(4) 0.0184(10) Uani 1 1 d . . . C15 C 0.4012(6) 0.6580(5) 0.4673(4) 0.0224(10) Uani 1 1 d . . . H15 H 0.4682 0.7330 0.4174 0.027 Uiso 1 1 calc R . . C16 C 0.4027(7) 0.6015(6) 0.5766(5) 0.0271(11) Uani 1 1 d . . . H16 H 0.4699 0.6409 0.6004 0.032 Uiso 1 1 calc R . . C17 C 0.2205(7) 0.4400(6) 0.6152(5) 0.0299(12) Uani 1 1 d . . . H17 H 0.1588 0.3615 0.6656 0.036 Uiso 1 1 calc R . . C18 C 0.2097(6) 0.4945(6) 0.5068(4) 0.0234(11) Uani 1 1 d . . . H18 H 0.1392 0.4553 0.4856 0.028 Uiso 1 1 calc R . . C19 C 0.1841(6) 0.5729(5) 0.2119(4) 0.0199(10) Uani 1 1 d . . . C20 C 0.1079(6) 0.6423(6) 0.1339(4) 0.0250(11) Uani 1 1 d . . . C21 C 0.1317(6) 0.6148(6) 0.0389(4) 0.0250(11) Uani 1 1 d . . . C22 C 0.2294(7) 0.5145(6) 0.0189(4) 0.0278(12) Uani 1 1 d . . . C23 C 0.2995(7) 0.4410(6) 0.0992(5) 0.0302(12) Uani 1 1 d . . . C24 C 0.2751(7) 0.4679(6) 0.1947(4) 0.0239(11) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I1 0.0346(2) 0.0415(2) 0.0215(2) -0.01776(16) -0.00723(16) -0.00191(17) I2 0.0397(2) 0.0381(2) 0.0236(2) -0.01649(16) -0.01199(17) 0.00104(18) F1 0.053(2) 0.0330(18) 0.0235(17) -0.0086(14) -0.0028(16) -0.0101(16) F2 0.051(2) 0.041(2) 0.0335(19) -0.0157(16) -0.0046(17) -0.0196(17) F3 0.043(2) 0.046(2) 0.0243(17) -0.0147(15) -0.0013(15) -0.0072(16) F4 0.0333(19) 0.0353(18) 0.039(2) -0.0190(16) -0.0048(15) -0.0072(14) F5 0.0336(18) 0.0352(17) 0.0320(18) -0.0187(14) -0.0153(15) 0.0087(14) F6 0.040(2) 0.0426(19) 0.0228(17) -0.0100(15) -0.0179(15) 0.0067(15) F7 0.059(3) 0.047(2) 0.044(2) -0.0295(18) -0.0246(19) 0.0279(19) F8 0.045(2) 0.0379(19) 0.0325(19) -0.0137(15) -0.0275(16) 0.0195(16) O1 0.0261(19) 0.035(2) 0.0222(19) -0.0200(16) -0.0128(15) 0.0091(16) O2 0.0254(19) 0.0322(19) 0.0186(18) -0.0124(15) -0.0070(15) -0.0019(15) N1 0.041(3) 0.033(3) 0.025(3) -0.009(2) -0.014(2) -0.001(2) N2 0.042(3) 0.040(3) 0.016(2) -0.012(2) -0.010(2) 0.006(2) C1 0.029(3) 0.025(3) 0.023(3) -0.009(2) -0.006(2) 0.003(2) C2 0.037(3) 0.028(3) 0.030(3) -0.016(2) -0.012(2) -0.003(2) C3 0.034(3) 0.027(3) 0.020(3) -0.014(2) -0.013(2) 0.004(2) C4 0.027(3) 0.029(3) 0.016(2) -0.008(2) -0.003(2) 0.004(2) C5 0.024(3) 0.028(3) 0.025(3) -0.015(2) -0.006(2) 0.001(2) C6 0.029(3) 0.024(2) 0.021(3) -0.014(2) -0.011(2) 0.007(2) C7 0.020(2) 0.025(3) 0.021(3) -0.012(2) -0.008(2) 0.0007(19) C8 0.024(3) 0.022(2) 0.022(3) -0.011(2) -0.009(2) 0.004(2) C9 0.033(3) 0.023(3) 0.032(3) -0.015(2) -0.013(2) 0.019(2) C10 0.045(4) 0.029(3) 0.030(3) -0.006(2) -0.021(3) 0.010(3) C11 0.037(3) 0.031(3) 0.019(3) -0.010(2) -0.003(2) -0.001(2) C12 0.031(3) 0.021(2) 0.019(3) -0.006(2) -0.007(2) 0.000(2) C13 0.022(2) 0.026(2) 0.017(2) -0.011(2) -0.0106(19) 0.0013(19) C14 0.023(3) 0.020(2) 0.011(2) -0.0055(18) -0.0020(19) 0.0006(19) C15 0.024(3) 0.021(2) 0.025(3) -0.010(2) -0.010(2) 0.0031(19) C16 0.035(3) 0.031(3) 0.024(3) -0.015(2) -0.016(2) 0.008(2) C17 0.036(3) 0.029(3) 0.020(3) -0.004(2) -0.006(2) 0.001(2) C18 0.021(3) 0.033(3) 0.018(3) -0.013(2) -0.001(2) -0.007(2) C19 0.029(3) 0.021(2) 0.012(2) -0.0076(19) -0.006(2) -0.002(2) C20 0.025(3) 0.031(3) 0.023(3) -0.014(2) -0.005(2) 0.001(2) C21 0.028(3) 0.034(3) 0.016(2) -0.008(2) -0.011(2) -0.001(2) C22 0.029(3) 0.042(3) 0.020(3) -0.019(2) -0.005(2) -0.006(2) C23 0.035(3) 0.029(3) 0.032(3) -0.018(2) -0.007(3) 0.007(2) C24 0.037(3) 0.027(3) 0.014(2) -0.006(2) -0.019(2) 0.004(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I1 C22 2.103(5) . ? I2 C3 2.100(5) . ? F1 C1 1.329(6) . ? F2 C2 1.348(6) . ? F3 C4 1.350(6) . ? F4 C5 1.354(6) . ? F5 C20 1.340(6) . ? F6 C21 1.347(6) . ? F7 C23 1.354(7) . ? F8 C24 1.357(6) . ? O1 C6 1.359(6) . ? O1 C7 1.449(6) . ? O2 C19 1.369(6) . ? O2 C13 1.450(6) . ? N1 C10 1.312(9) . ? N1 C11 1.338(8) . ? N2 C17 1.327(8) . ? N2 C16 1.350(8) . ? C1 C2 1.384(8) . ? C1 C6 1.396(8) . ? C2 C3 1.378(8) . ? C3 C4 1.389(8) . ? C4 C5 1.385(8) . ? C5 C6 1.381(8) . ? C7 C8 1.522(7) . ? C7 C13 1.538(7) . ? C7 H7 1.0000 . ? C8 C12 1.396(8) . ? C8 C9 1.400(7) . ? C9 C10 1.386(8) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C11 C12 1.382(7) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C14 1.513(6) . ? C13 H13 1.0000 . ? C14 C18 1.374(7) . ? C14 C15 1.389(7) . ? C15 C16 1.384(7) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 C18 1.398(7) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? C19 C24 1.380(8) . ? C19 C20 1.382(7) . ? C20 C21 1.380(7) . ? C21 C22 1.385(8) . ? C22 C23 1.376(8) . ? C23 C24 1.382(8) . ? 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 C6 O1 C7 116.9(4) . . ? C19 O2 C13 115.3(4) . . ? C10 N1 C11 117.2(5) . . ? C17 N2 C16 117.0(5) . . ? F1 C1 C2 120.0(5) . . ? F1 C1 C6 119.9(5) . . ? C2 C1 C6 120.2(5) . . ? F2 C2 C3 119.6(5) . . ? F2 C2 C1 117.9(5) . . ? C3 C2 C1 122.5(5) . . ? C2 C3 C4 117.0(5) . . ? C2 C3 I2 121.9(4) . . ? C4 C3 I2 121.1(4) . . ? F3 C4 C5 118.0(5) . . ? F3 C4 C3 120.8(5) . . ? C5 C4 C3 121.2(5) . . ? F4 C5 C6 119.9(5) . . ? F4 C5 C4 118.6(5) . . ? C6 C5 C4 121.5(5) . . ? O1 C6 C5 120.4(5) . . ? O1 C6 C1 122.0(5) . . ? C5 C6 C1 117.5(5) . . ? O1 C7 C8 107.8(4) . . ? O1 C7 C13 109.3(4) . . ? C8 C7 C13 113.8(4) . . ? O1 C7 H7 108.6 . . ? C8 C7 H7 108.6 . . ? C13 C7 H7 108.6 . . ? C12 C8 C9 117.6(5) . . ? C12 C8 C7 120.5(5) . . ? C9 C8 C7 121.8(5) . . ? C10 C9 C8 118.1(5) . . ? C10 C9 H9 120.9 . . ? C8 C9 H9 120.9 . . ? N1 C10 C9 124.6(6) . . ? N1 C10 H10 117.7 . . ? C9 C10 H10 117.7 . . ? N1 C11 C12 123.5(6) . . ? N1 C11 H11 118.2 . . ? C12 C11 H11 118.2 . . ? C11 C12 C8 118.8(5) . . ? C11 C12 H12 120.6 . . ? C8 C12 H12 120.6 . . ? O2 C13 C14 108.2(4) . . ? O2 C13 C7 110.1(4) . . ? C14 C13 C7 112.1(4) . . ? O2 C13 H13 108.8 . . ? C14 C13 H13 108.8 . . ? C7 C13 H13 108.8 . . ? C18 C14 C15 117.2(5) . . ? C18 C14 C13 121.8(5) . . ? C15 C14 C13 121.0(4) . . ? C16 C15 C14 119.7(5) . . ? C16 C15 H15 120.1 . . ? C14 C15 H15 120.1 . . ? N2 C16 C15 123.0(5) . . ? N2 C16 H16 118.5 . . ? C15 C16 H16 118.5 . . ? N2 C17 C18 123.1(5) . . ? N2 C17 H17 118.5 . . ? C18 C17 H17 118.5 . . ? C14 C18 C17 119.9(5) . . ? C14 C18 H18 120.0 . . ? C17 C18 H18 120.0 . . ? O2 C19 C24 122.5(4) . . ? O2 C19 C20 120.4(5) . . ? C24 C19 C20 117.1(5) . . ? F5 C20 C21 119.3(5) . . ? F5 C20 C19 119.6(5) . . ? C21 C20 C19 121.0(5) . . ? F6 C21 C20 118.1(5) . . ? F6 C21 C22 120.2(5) . . ? C20 C21 C22 121.7(5) . . ? C23 C22 C21 117.0(5) . . ? C23 C22 I1 123.1(4) . . ? C21 C22 I1 119.8(4) . . ? F7 C23 C22 119.7(5) . . ? F7 C23 C24 118.9(5) . . ? C22 C23 C24 121.4(5) . . ? F8 C24 C19 119.2(4) . . ? F8 C24 C23 119.2(5) . . ? C19 C24 C23 121.6(5) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag F1 C1 C2 F2 -0.6(8) . . . . ? C6 C1 C2 F2 177.5(5) . . . . ? F1 C1 C2 C3 178.0(5) . . . . ? C6 C1 C2 C3 -3.9(9) . . . . ? F2 C2 C3 C4 178.8(5) . . . . ? C1 C2 C3 C4 0.2(9) . . . . ? F2 C2 C3 I2 -4.2(8) . . . . ? C1 C2 C3 I2 177.2(4) . . . . ? C2 C3 C4 F3 -178.9(5) . . . . ? I2 C3 C4 F3 4.1(7) . . . . ? C2 C3 C4 C5 2.1(8) . . . . ? I2 C3 C4 C5 -174.9(4) . . . . ? F3 C4 C5 F4 0.3(8) . . . . ? C3 C4 C5 F4 179.3(5) . . . . ? F3 C4 C5 C6 -179.7(5) . . . . ? C3 C4 C5 C6 -0.7(8) . . . . ? C7 O1 C6 C5 -123.8(5) . . . . ? C7 O1 C6 C1 58.9(7) . . . . ? F4 C5 C6 O1 -0.5(8) . . . . ? C4 C5 C6 O1 179.6(5) . . . . ? F4 C5 C6 C1 177.0(5) . . . . ? C4 C5 C6 C1 -2.9(8) . . . . ? F1 C1 C6 O1 0.7(8) . . . . ? C2 C1 C6 O1 -177.4(5) . . . . ? F1 C1 C6 C5 -176.8(5) . . . . ? C2 C1 C6 C5 5.1(8) . . . . ? C6 O1 C7 C8 -140.1(4) . . . . ? C6 O1 C7 C13 95.8(5) . . . . ? O1 C7 C8 C12 -166.5(5) . . . . ? C13 C7 C8 C12 -45.2(6) . . . . ? O1 C7 C8 C9 16.2(7) . . . . ? C13 C7 C8 C9 137.6(5) . . . . ? C12 C8 C9 C10 2.5(8) . . . . ? C7 C8 C9 C10 179.8(5) . . . . ? C11 N1 C10 C9 -0.9(10) . . . . ? C8 C9 C10 N1 -0.5(10) . . . . ? C10 N1 C11 C12 0.3(9) . . . . ? N1 C11 C12 C8 1.7(9) . . . . ? C9 C8 C12 C11 -3.0(8) . . . . ? C7 C8 C12 C11 179.6(5) . . . . ? C19 O2 C13 C14 -140.7(4) . . . . ? C19 O2 C13 C7 96.5(5) . . . . ? O1 C7 C13 O2 59.3(5) . . . . ? C8 C7 C13 O2 -61.2(5) . . . . ? O1 C7 C13 C14 -61.1(5) . . . . ? C8 C7 C13 C14 178.3(4) . . . . ? O2 C13 C14 C18 12.2(7) . . . . ? C7 C13 C14 C18 133.8(5) . . . . ? O2 C13 C14 C15 -169.3(4) . . . . ? C7 C13 C14 C15 -47.8(6) . . . . ? C18 C14 C15 C16 -1.3(8) . . . . ? C13 C14 C15 C16 -179.9(5) . . . . ? C17 N2 C16 C15 0.1(9) . . . . ? C14 C15 C16 N2 1.6(9) . . . . ? C16 N2 C17 C18 -2.2(9) . . . . ? C15 C14 C18 C17 -0.6(8) . . . . ? C13 C14 C18 C17 178.0(5) . . . . ? N2 C17 C18 C14 2.4(9) . . . . ? C13 O2 C19 C24 65.8(6) . . . . ? C13 O2 C19 C20 -115.7(5) . . . . ? O2 C19 C20 F5 -0.1(8) . . . . ? C24 C19 C20 F5 178.5(5) . . . . ? O2 C19 C20 C21 176.4(5) . . . . ? C24 C19 C20 C21 -5.1(8) . . . . ? F5 C20 C21 F6 0.1(8) . . . . ? C19 C20 C21 F6 -176.3(5) . . . . ? F5 C20 C21 C22 178.2(5) . . . . ? C19 C20 C21 C22 1.7(9) . . . . ? F6 C21 C22 C23 179.4(5) . . . . ? C20 C21 C22 C23 1.4(9) . . . . ? F6 C21 C22 I1 2.5(7) . . . . ? C20 C21 C22 I1 -175.5(4) . . . . ? C21 C22 C23 F7 179.4(5) . . . . ? I1 C22 C23 F7 -3.8(8) . . . . ? C21 C22 C23 C24 -1.0(9) . . . . ? I1 C22 C23 C24 175.8(4) . . . . ? O2 C19 C24 F8 2.3(8) . . . . ? C20 C19 C24 F8 -176.2(5) . . . . ? O2 C19 C24 C23 -176.0(5) . . . . ? C20 C19 C24 C23 5.5(8) . . . . ? F7 C23 C24 F8 -1.2(8) . . . . ? C22 C23 C24 F8 179.2(5) . . . . ? F7 C23 C24 C19 177.1(5) . . . . ? C22 C23 C24 C19 -2.5(9) . . . . ? _diffrn_measured_fraction_theta_max 0.840 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 2.285 _refine_diff_density_min -1.806 _refine_diff_density_rms 0.158 _iucr_refine_instructions_details ; TITL twin5 in P -1 CELL 0.71073 9.3175 10.3237 13.5796 68.372 74.546 85.996 ZERR 2.00 0.0006 0.0006 0.0007 0.002 0.003 0.003 LATT 1 SFAC C H N O F I UNIT 48 20 4 4 16 4 L.S. 4 BOND $H CONF ACTA FMAP 2 PLAN 20 OMIT 0 0 1 mERG 0 SIZE 0.100 0.160 0.180 TEMP -170.000 WGHT 0.095000 1.462500 FVAR 0.33928 MOLE 1 I1 6 0.272649 0.487861 -0.132477 11.00000 0.03456 0.04147 = 0.02150 -0.01776 -0.00723 -0.00191 I2 6 0.240429 1.002586 0.728233 11.00000 0.03970 0.03806 = 0.02356 -0.01649 -0.01199 0.00104 F1 5 0.359045 1.078751 0.298909 11.00000 0.05264 0.03298 = 0.02347 -0.00857 -0.00281 -0.01010 F2 5 0.394363 1.133339 0.469407 11.00000 0.05127 0.04128 = 0.03351 -0.01567 -0.00464 -0.01961 F3 5 0.013158 0.797823 0.707243 11.00000 0.04273 0.04574 = 0.02435 -0.01471 -0.00134 -0.00716 F4 5 -0.013739 0.737285 0.538135 11.00000 0.03334 0.03530 = 0.03879 -0.01900 -0.00477 -0.00721 F5 5 0.015254 0.743074 0.147935 11.00000 0.03363 0.03515 = 0.03199 -0.01871 -0.01532 0.00870 F6 5 0.060234 0.691480 -0.036570 11.00000 0.04045 0.04259 = 0.02279 -0.00997 -0.01788 0.00674 F7 5 0.395166 0.340623 0.084840 11.00000 0.05914 0.04688 = 0.04364 -0.02949 -0.02465 0.02788 F8 5 0.345523 0.391457 0.272171 11.00000 0.04456 0.03786 = 0.03251 -0.01369 -0.02749 0.01952 O1 4 0.162507 0.868430 0.329945 11.00000 0.02609 0.03480 = 0.02216 -0.02001 -0.01282 0.00907 O2 4 0.165459 0.606729 0.302975 11.00000 0.02536 0.03218 = 0.01861 -0.01243 -0.00701 -0.00191 N1 3 0.298975 1.006096 -0.074971 11.00000 0.04114 0.03265 = 0.02495 -0.00898 -0.01394 -0.00067 N2 3 0.312920 0.492907 0.651041 11.00000 0.04171 0.03997 = 0.01588 -0.01232 -0.01050 0.00552 C1 1 0.276785 1.007233 0.399093 11.00000 0.02922 0.02514 = 0.02309 -0.00872 -0.00624 0.00307 C2 1 0.292941 1.034428 0.488114 11.00000 0.03655 0.02819 = 0.02993 -0.01622 -0.01174 -0.00279 C3 1 0.207618 0.966483 0.593281 11.00000 0.03365 0.02681 = 0.02028 -0.01381 -0.01271 0.00447 C4 1 0.103042 0.867519 0.607142 11.00000 0.02677 0.02900 = 0.01650 -0.00840 -0.00303 0.00426 C5 1 0.089230 0.835729 0.519455 11.00000 0.02370 0.02791 = 0.02499 -0.01450 -0.00568 0.00065 C6 1 0.177501 0.902022 0.414615 11.00000 0.02899 0.02369 = 0.02099 -0.01357 -0.01148 0.00652 C7 1 0.294950 0.824189 0.267548 11.00000 0.02007 0.02516 = 0.02059 -0.01210 -0.00750 0.00069 AFIX 13 H7 2 0.384470 0.861130 0.277358 11.00000 -1.20000 AFIX 0 C8 1 0.295197 0.888401 0.146998 11.00000 0.02400 0.02249 = 0.02234 -0.01144 -0.00903 0.00360 C9 1 0.204500 0.999502 0.108574 11.00000 0.03297 0.02327 = 0.03155 -0.01540 -0.01350 0.01877 AFIX 43 H9 2 0.139728 1.037649 0.157259 11.00000 -1.20000 AFIX 0 C10 1 0.211899 1.052231 -0.002476 11.00000 0.04547 0.02942 = 0.03037 -0.00596 -0.02082 0.01014 AFIX 43 H10 2 0.149479 1.127105 -0.027908 11.00000 -1.20000 AFIX 0 C11 1 0.387998 0.901905 -0.038600 11.00000 0.03696 0.03061 = 0.01909 -0.01033 -0.00346 -0.00139 AFIX 43 H11 2 0.452082 0.867635 -0.090175 11.00000 -1.20000 AFIX 0 C12 1 0.391698 0.841512 0.069932 11.00000 0.03131 0.02060 = 0.01861 -0.00569 -0.00739 0.00019 AFIX 43 H12 2 0.458683 0.769398 0.091723 11.00000 -1.20000 AFIX 0 C13 1 0.297178 0.664007 0.311870 11.00000 0.02212 0.02601 = 0.01674 -0.01094 -0.01061 0.00131 AFIX 13 H13 2 0.387434 0.634247 0.267126 11.00000 -1.20000 AFIX 0 C14 1 0.301391 0.604735 0.430875 11.00000 0.02273 0.02012 = 0.01066 -0.00546 -0.00201 0.00064 C15 1 0.401212 0.658046 0.467314 11.00000 0.02425 0.02075 = 0.02518 -0.00976 -0.00996 0.00315 AFIX 43 H15 2 0.468172 0.732978 0.417417 11.00000 -1.20000 AFIX 0 C16 1 0.402658 0.601498 0.576631 11.00000 0.03511 0.03098 = 0.02366 -0.01476 -0.01631 0.00765 AFIX 43 H16 2 0.469899 0.640912 0.600403 11.00000 -1.20000 AFIX 0 C17 1 0.220534 0.440029 0.615222 11.00000 0.03572 0.02905 = 0.02027 -0.00444 -0.00622 0.00150 AFIX 43 H17 2 0.158822 0.361503 0.665602 11.00000 -1.20000 AFIX 0 C18 1 0.209742 0.494476 0.506772 11.00000 0.02098 0.03282 = 0.01821 -0.01260 -0.00124 -0.00732 AFIX 43 H18 2 0.139159 0.455304 0.485589 11.00000 -1.20000 AFIX 0 C19 1 0.184074 0.572941 0.211947 11.00000 0.02885 0.02124 = 0.01187 -0.00761 -0.00585 -0.00201 C20 1 0.107918 0.642337 0.133948 11.00000 0.02463 0.03120 = 0.02250 -0.01403 -0.00517 0.00073 C21 1 0.131742 0.614806 0.038914 11.00000 0.02775 0.03407 = 0.01596 -0.00831 -0.01101 -0.00085 C22 1 0.229442 0.514483 0.018865 11.00000 0.02888 0.04201 = 0.01997 -0.01948 -0.00495 -0.00626 C23 1 0.299503 0.441009 0.099217 11.00000 0.03509 0.02854 = 0.03153 -0.01785 -0.00747 0.00708 C24 1 0.275146 0.467907 0.194740 11.00000 0.03692 0.02658 = 0.01367 -0.00588 -0.01850 0.00437 HKLF 5 END ;