# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Dr Pierangelo Metrangolo' _publ_contact_author_address ; NFMLab-Department of Chemistry Polytechnic of Milan Via L. Mancinelli 7 Milan 20131 ITALY ; _publ_contact_author_email PIERANGELO.METRANGOLO@POLIMI.IT _publ_section_title ; Spontaneous resolution in a halogen bonded supramolecular architecture ; loop_ _publ_author_name 'Pierangelo Metrangolo' 'Emanuela Guido' 'Rosalba Liantonio' 'Hannes Neukirch' 'Tullio Pilati' 'Giuseppe Resnati' data_re24 _database_code_depnum_ccdc_archive 'CCDC 256351' _audit_creation_method SHELXL-97 _audit_update_record ; Checkcif ; _chemical_name_systematic ; N,N,N',N'-tetramethyl-p-phenylenediamine.1,8-diiodioperfluorooctane ; _chemical_name_common ; N,N,N',N'-tetramethyl-p-phenylenediamine.1,8- diiodioperfluorooctane ; _chemical_formula_moiety '(C10 H16 N2), (C8 F16 I2)' _chemical_formula_sum 'C18 H16 F16 I2 N2' _chemical_formula_weight 818.13 _chemical_absolute_configuration ad 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' 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 6.1910(10) _cell_length_b 19.168(3) _cell_length_c 21.858(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2593.9(8) _cell_formula_units_Z 4 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 6525 _cell_measurement_theta_min 4.641 _cell_measurement_theta_max 53.785 _exptl_crystal_description ellipsoid _exptl_crystal_colour yellow _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.20 _exptl_crystal_density_diffrn 2.093 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1552 _exptl_absorpt_coefficient_mu 2.549 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Bruker, 1997)' _exptl_absorpt_correction_T_min 0.822166 _exptl_absorpt_correction_T_max 1.000000 _exptl_special_details ; The crystals are very large. It was very diffult to reduce their dimension to a reasonable value, useful for X-ray diffraction experiment. In fact, they are easily deformed in the directions perpendicular the chain ...TMPA...PFC...TMPA...PFC..., and crack perpendicularly. The problem was solved by partial dissolution of a crystal in chlorofor. ; _diffrn_ambient_temperature 291(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX' _diffrn_measurement_method '\w scans' _diffrn_standards_decay_% 0.00 _diffrn_reflns_number 70753 _diffrn_reflns_av_R_equivalents 0.0293 _diffrn_reflns_av_sigmaI/netI 0.0335 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 1.41 _diffrn_reflns_theta_max 32.02 _reflns_number_total 8973 _reflns_number_gt 6727 _reflns_threshold_expression >2\s(I) _computing_data_collection 'SMART (Bruker, 1995)' _computing_cell_refinement 'SAINT, (Bruker 1997)' _computing_data_reduction 'SAINT, (Bruker 1997)' _computing_structure_solution 'SIR-92, (Altomare et al, 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPIII (Burnett & Johnson,1996)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0413P)^2^] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.017(18) _refine_ls_number_reflns 8973 _refine_ls_number_parameters 559 _refine_ls_number_restraints 1378 _refine_ls_R_factor_all 0.0476 _refine_ls_R_factor_gt 0.0349 _refine_ls_wR_factor_ref 0.0827 _refine_ls_wR_factor_gt 0.0787 _refine_ls_goodness_of_fit_ref 0.946 _refine_ls_restrained_S_all 0.962 _refine_ls_shift/su_max 0.005 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I1 I 0.55183(5) -0.156939(11) 0.131442(13) 0.06655(8) Uani 1 d D . . I2 I -0.52697(4) 0.381266(11) 0.154967(12) 0.06137(7) Uani 1 d D . . C11A C 0.3493(18) -0.0694(4) 0.1551(6) 0.071(3) Uani 0.50 d PDU A 1 C12A C 0.276(2) -0.0286(6) 0.1011(6) 0.072(3) Uani 0.50 d PDU A 1 C13A C 0.1332(17) 0.0381(5) 0.1155(5) 0.076(3) Uani 0.50 d PDU A 1 C14A C 0.1074(17) 0.0899(5) 0.0629(6) 0.079(3) Uani 0.50 d PDU A 1 C15A C -0.0721(17) 0.1452(5) 0.0692(5) 0.079(3) Uani 0.50 d PDU A 1 C16A C -0.1007(19) 0.1903(6) 0.1269(5) 0.070(3) Uani 0.50 d PDU A 1 C17A C -0.254(3) 0.2560(8) 0.1179(7) 0.068(4) Uani 0.50 d PDU A 1 C18A C -0.3064(16) 0.2969(4) 0.1747(6) 0.057(3) Uani 0.50 d PDU A 1 F16A F -0.1158(16) 0.3188(7) 0.1964(7) 0.085(3) Uani 0.50 d PDU A 1 F15A F -0.3868(16) 0.2519(6) 0.2148(4) 0.088(3) Uani 0.50 d PDU A 1 F14A F -0.441(3) 0.2351(13) 0.0920(7) 0.081(4) Uani 0.50 d PDU A 1 F13A F -0.149(3) 0.2966(11) 0.0767(7) 0.065(2) Uani 0.50 d PDU A 1 F12A F 0.0943(12) 0.2142(4) 0.1422(5) 0.113(3) Uani 0.50 d PDU A 1 F11A F -0.1747(14) 0.1518(4) 0.1722(3) 0.098(2) Uani 0.50 d PDU A 1 F10A F -0.2525(8) 0.1114(3) 0.0561(3) 0.0927(17) Uani 0.50 d PDU A 1 F9A F -0.0316(19) 0.1860(5) 0.0190(4) 0.122(3) Uani 0.50 d PDU A 1 F8A F 0.2969(10) 0.1230(4) 0.0565(4) 0.124(3) Uani 0.50 d PDU A 1 F7A F 0.088(3) 0.0459(6) 0.0139(6) 0.109(4) Uani 0.50 d PDU A 1 F6A F -0.0657(10) 0.0158(3) 0.1295(4) 0.103(2) Uani 0.50 d PDU A 1 F5A F 0.2036(14) 0.0746(3) 0.1641(3) 0.094(2) Uani 0.50 d PDU A 1 F4A F 0.442(2) -0.0242(6) 0.0600(7) 0.158(6) Uani 0.50 d PDU A 1 F3A F 0.126(2) -0.0692(7) 0.0721(9) 0.078(3) Uani 0.50 d PDU A 1 F2A F 0.166(2) -0.0871(7) 0.1818(8) 0.096(4) Uani 0.50 d PDU A 1 F1A F 0.4628(18) -0.0256(5) 0.1901(4) 0.094(3) Uani 0.50 d PDU A 1 C18B C -0.3480(19) 0.2860(4) 0.1695(7) 0.071(3) Uani 0.50 d PDU A 2 C17B C -0.254(3) 0.2537(7) 0.1123(6) 0.048(2) Uani 0.50 d PDU A 2 C16B C -0.1272(17) 0.1841(6) 0.1216(5) 0.060(3) Uani 0.50 d PDU A 2 C15B C -0.0232(17) 0.1541(6) 0.0604(4) 0.067(3) Uani 0.50 d PDU A 2 C14B C 0.0384(17) 0.0752(5) 0.0604(5) 0.073(3) Uani 0.50 d PDU A 2 C13B C 0.1772(18) 0.0477(6) 0.1120(5) 0.072(3) Uani 0.50 d PDU A 2 C12B C 0.285(2) -0.0252(6) 0.0955(6) 0.066(3) Uani 0.50 d PDU A 2 C11B C 0.3874(18) -0.0599(4) 0.1494(7) 0.074(3) Uani 0.50 d PDU A 2 F16B F -0.1909(19) 0.3021(8) 0.2098(7) 0.107(4) Uani 0.50 d PDU A 2 F15B F -0.4798(15) 0.2413(6) 0.1973(5) 0.095(3) Uani 0.50 d PDU A 2 F14B F -0.419(3) 0.2394(11) 0.0757(6) 0.065(3) Uani 0.50 d PDU A 2 F13B F -0.123(4) 0.3016(12) 0.0889(8) 0.097(5) Uani 0.50 d PDU A 2 F12B F -0.2690(10) 0.1371(3) 0.1440(3) 0.084(2) Uani 0.50 d PDU A 2 F11B F 0.0202(12) 0.1921(4) 0.1663(3) 0.0770(18) Uani 0.50 d PDU A 2 F10B F 0.1517(9) 0.1931(3) 0.0547(3) 0.0803(14) Uani 0.50 d PDU A 2 F9B F -0.1588(14) 0.1647(5) 0.0164(4) 0.100(3) Uani 0.50 d PDU A 2 F8B F -0.1420(10) 0.0380(3) 0.0570(3) 0.0993(19) Uani 0.50 d PDU A 2 F7B F 0.142(2) 0.0674(6) 0.0078(5) 0.094(3) Uani 0.50 d PDU A 2 F6B F 0.3357(9) 0.0939(3) 0.1244(4) 0.0976(19) Uani 0.50 d PDU A 2 F5B F 0.0550(12) 0.0444(3) 0.1632(2) 0.0769(15) Uani 0.50 d PDU A 2 F4B F 0.169(3) -0.0737(9) 0.0636(10) 0.121(6) Uani 0.50 d PDU A 2 F3B F 0.4501(16) -0.0057(4) 0.0601(4) 0.0701(17) Uani 0.50 d PDU A 2 F2B F 0.236(2) -0.0703(8) 0.1917(7) 0.107(4) Uani 0.50 d PDU A 2 F1B F 0.5261(19) -0.0094(5) 0.1684(5) 0.111(4) Uani 0.50 d PDU A 2 C1 C 0.6643(6) -0.33474(16) 0.12703(16) 0.0512(7) Uani 1 d . . . C2 C 0.5955(7) -0.36106(19) 0.18353(16) 0.0616(9) Uani 1 d . . . H2 H 0.6550 -0.3428 0.2192 0.074 Uiso 1 calc R . . C3 C 0.4429(7) -0.41298(19) 0.18813(15) 0.0618(8) Uani 1 d . . . H3 H 0.4034 -0.4289 0.2267 0.074 Uiso 1 calc R . . C4 C 0.3460(5) -0.44238(15) 0.13687(15) 0.0482(7) Uani 1 d . . . C5 C 0.4138(7) -0.4163(2) 0.08114(16) 0.0648(10) Uani 1 d . . . H5 H 0.3539 -0.4345 0.0455 0.078 Uiso 1 calc R . . C6 C 0.5666(8) -0.36430(19) 0.07619(15) 0.0652(10) Uani 1 d . . . H6 H 0.6054 -0.3485 0.0375 0.078 Uiso 1 calc R . . N1 N 0.8127(5) -0.27883(16) 0.12229(16) 0.0593(7) Uani 1 d . . . N2 N 0.1978(5) -0.49827(15) 0.14190(15) 0.0573(7) Uani 1 d . . . C7 C 0.9242(9) -0.2719(3) 0.0630(2) 0.0940(16) Uani 1 d . . . H7A H 1.0197 -0.2324 0.0643 0.141 Uiso 1 calc R . . H7B H 0.8195 -0.2652 0.0312 0.141 Uiso 1 calc R . . H7C H 1.0060 -0.3134 0.0550 0.141 Uiso 1 calc R . . C8 C 0.9595(9) -0.2694(3) 0.1752(3) 0.0933(15) Uani 1 d . . . H8A H 1.0532 -0.2304 0.1678 0.140 Uiso 1 calc R . . H8B H 1.0445 -0.3108 0.1808 0.140 Uiso 1 calc R . . H8C H 0.8758 -0.2609 0.2114 0.140 Uiso 1 calc R . . C9 C 0.0714(8) -0.5007(2) 0.1991(2) 0.0790(12) Uani 1 d . . . H9A H -0.0234 -0.5403 0.1983 0.119 Uiso 1 calc R . . H9B H -0.0125 -0.4588 0.2029 0.119 Uiso 1 calc R . . H9C H 0.1677 -0.5045 0.2334 0.119 Uiso 1 calc R . . C10 C 0.0656(8) -0.5127(2) 0.0884(2) 0.0801(12) Uani 1 d . . . H10A H -0.0280 -0.5514 0.0968 0.120 Uiso 1 calc R . . H10B H 0.1571 -0.5238 0.0544 0.120 Uiso 1 calc R . . H10C H -0.0197 -0.4723 0.0788 0.120 Uiso 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I1 0.06702(15) 0.04591(11) 0.08671(16) 0.00040(11) 0.00194(13) 0.00951(11) I2 0.06244(13) 0.04725(10) 0.07442(14) 0.00162(10) 0.00125(12) 0.00975(10) C11A 0.088(7) 0.057(5) 0.066(5) 0.003(5) 0.025(5) 0.009(5) C12A 0.073(6) 0.066(6) 0.078(6) -0.016(5) 0.003(5) 0.026(5) C13A 0.074(5) 0.063(5) 0.090(6) -0.003(5) -0.011(5) 0.017(5) C14A 0.083(6) 0.064(5) 0.092(6) 0.000(4) 0.001(5) -0.003(5) C15A 0.072(5) 0.050(4) 0.115(7) 0.003(5) 0.025(5) 0.010(4) C16A 0.069(6) 0.048(5) 0.092(6) -0.002(5) 0.012(6) 0.010(4) C17A 0.066(6) 0.054(6) 0.083(7) 0.010(6) -0.009(6) -0.004(6) C18A 0.062(5) 0.048(4) 0.061(5) 0.007(4) -0.010(4) 0.010(4) F16A 0.069(5) 0.071(4) 0.115(8) -0.020(4) -0.040(5) 0.016(3) F15A 0.113(7) 0.082(5) 0.070(5) 0.032(4) 0.020(4) 0.027(5) F14A 0.066(4) 0.078(5) 0.099(10) -0.008(8) -0.015(7) 0.004(4) F13A 0.078(5) 0.057(5) 0.058(3) 0.010(3) 0.010(3) 0.007(4) F12A 0.071(4) 0.073(5) 0.197(10) -0.031(5) -0.042(6) 0.015(3) F11A 0.141(7) 0.068(4) 0.084(4) 0.008(3) -0.001(4) 0.033(4) F10A 0.067(3) 0.079(3) 0.132(5) -0.019(4) -0.019(3) 0.022(3) F9A 0.175(10) 0.103(6) 0.089(5) 0.021(4) 0.052(7) 0.030(7) F8A 0.072(4) 0.116(5) 0.184(7) 0.023(6) 0.037(4) -0.007(4) F7A 0.149(8) 0.101(8) 0.077(6) -0.018(6) -0.004(6) 0.022(6) F6A 0.087(4) 0.078(4) 0.144(6) 0.034(4) 0.041(4) 0.012(3) F5A 0.116(5) 0.082(4) 0.083(4) -0.029(3) -0.036(4) 0.034(4) F4A 0.138(9) 0.142(10) 0.195(9) 0.119(7) 0.061(8) 0.054(8) F3A 0.074(4) 0.062(4) 0.098(5) -0.037(4) -0.022(4) 0.011(4) F2A 0.097(7) 0.061(4) 0.129(10) 0.028(5) 0.050(6) 0.012(4) F1A 0.146(10) 0.057(4) 0.078(4) -0.019(3) -0.050(5) 0.025(5) C18B 0.073(6) 0.057(5) 0.081(6) -0.007(5) -0.020(5) 0.014(5) C17B 0.051(5) 0.038(4) 0.057(5) -0.001(4) 0.000(4) 0.009(4) C16B 0.054(4) 0.048(4) 0.077(5) 0.009(4) -0.015(4) 0.004(4) C15B 0.084(6) 0.069(5) 0.047(3) 0.007(4) 0.009(4) 0.023(5) C14B 0.087(6) 0.063(5) 0.067(4) -0.003(4) 0.012(5) 0.008(5) C13B 0.076(5) 0.073(5) 0.066(5) 0.012(4) 0.013(4) -0.010(4) C12B 0.062(5) 0.062(5) 0.074(6) 0.021(5) 0.005(5) -0.012(5) C11B 0.065(5) 0.069(6) 0.087(7) 0.010(5) -0.002(5) 0.011(5) F16B 0.110(9) 0.116(10) 0.096(6) -0.028(6) -0.047(7) 0.043(6) F15B 0.106(7) 0.075(4) 0.104(7) 0.033(5) 0.030(5) 0.022(5) F14B 0.073(6) 0.064(4) 0.057(5) -0.004(4) -0.013(4) 0.015(4) F13B 0.100(8) 0.059(5) 0.133(12) 0.012(8) 0.023(8) -0.007(5) F12B 0.081(4) 0.044(2) 0.128(6) 0.015(3) 0.043(4) 0.005(2) F11B 0.084(5) 0.072(4) 0.075(3) -0.004(3) -0.020(3) 0.022(4) F10B 0.074(3) 0.071(3) 0.096(4) 0.019(3) 0.018(3) 0.014(3) F9B 0.127(7) 0.107(6) 0.068(4) -0.015(4) -0.035(5) 0.046(5) F8B 0.084(4) 0.077(3) 0.137(5) -0.027(4) -0.032(4) -0.008(3) F7B 0.156(9) 0.081(6) 0.046(3) 0.011(3) 0.027(4) 0.050(5) F6B 0.068(3) 0.070(3) 0.154(6) -0.002(4) -0.034(4) -0.003(3) F5B 0.098(4) 0.075(3) 0.058(3) 0.012(2) 0.030(3) 0.027(3) F4B 0.128(10) 0.108(8) 0.127(11) -0.018(7) -0.057(8) 0.034(7) F3B 0.078(4) 0.058(3) 0.074(3) 0.019(3) 0.039(3) 0.013(3) F2B 0.122(9) 0.112(10) 0.086(5) 0.013(6) 0.038(7) 0.052(7) F1B 0.089(5) 0.059(4) 0.183(11) -0.031(6) -0.030(7) -0.003(4) C1 0.0557(18) 0.0371(14) 0.0608(18) -0.0020(14) -0.0016(15) 0.0100(12) C2 0.074(2) 0.062(2) 0.0495(17) -0.0037(15) -0.0072(16) -0.0013(17) C3 0.073(2) 0.0636(19) 0.0487(17) 0.0027(14) 0.0028(18) -0.001(2) C4 0.0517(16) 0.0389(14) 0.0542(17) -0.0005(13) 0.0047(14) 0.0110(12) C5 0.084(3) 0.063(2) 0.0476(17) -0.0095(15) -0.0048(18) -0.007(2) C6 0.088(3) 0.0615(19) 0.0466(16) 0.0042(14) 0.0038(18) -0.010(2) N1 0.0565(17) 0.0481(14) 0.0732(19) -0.0004(14) -0.0018(15) 0.0060(13) N2 0.0567(16) 0.0471(14) 0.0683(19) -0.0012(13) 0.0033(14) 0.0047(12) C7 0.089(4) 0.086(3) 0.107(3) -0.005(3) 0.044(3) -0.021(3) C8 0.076(3) 0.074(3) 0.130(4) 0.011(3) -0.040(3) -0.009(2) C9 0.073(3) 0.072(2) 0.092(3) -0.003(2) 0.027(3) 0.004(2) C10 0.074(3) 0.077(3) 0.089(3) 0.003(2) -0.016(3) -0.008(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 C11A 2.157(5) . ? I1 C11B 2.157(5) . ? I2 C18A 2.159(5) . ? I2 C18B 2.159(5) . ? C11A F2A 1.322(11) . ? C11A F1A 1.337(11) . ? C11A C12A 1.486(11) . ? C12A F3A 1.367(11) . ? C12A F4A 1.367(11) . ? C12A C13A 1.585(10) . ? C13A F6A 1.339(11) . ? C13A F5A 1.346(11) . ? C13A C14A 1.528(11) . ? C14A F8A 1.341(10) . ? C14A F7A 1.369(11) . ? C14A C15A 1.542(11) . ? C15A F10A 1.322(11) . ? C15A F9A 1.369(11) . ? C15A C16A 1.539(11) . ? C16A F11A 1.316(11) . ? C16A F12A 1.334(12) . ? C16A C17A 1.589(11) . ? C17A F14A 1.350(11) . ? C17A F13A 1.353(11) . ? C17A C18A 1.504(11) . ? C18A F15A 1.328(10) . ? C18A F16A 1.339(11) . ? C18B F15B 1.329(12) . ? C18B F16B 1.349(11) . ? C18B C17B 1.510(11) . ? C17B F14B 1.325(11) . ? C17B F13B 1.326(11) . ? C17B C16B 1.562(10) . ? C16B F11B 1.345(10) . ? C16B F12B 1.349(11) . ? C16B C15B 1.592(11) . ? C15B F9B 1.293(9) . ? C15B F10B 1.321(11) . ? C15B C14B 1.558(12) . ? C14B F7B 1.325(10) . ? C14B F8B 1.328(10) . ? C14B C13B 1.512(12) . ? C13B F6B 1.349(11) . ? C13B F5B 1.352(10) . ? C13B C12B 1.589(12) . ? C12B F3B 1.337(10) . ? C12B F4B 1.366(11) . ? C12B C11B 1.494(11) . ? C11B F2B 1.333(11) . ? C11B F1B 1.358(11) . ? C1 C6 1.386(5) . ? C1 C2 1.400(5) . ? C1 N1 1.416(5) . ? C2 C3 1.376(6) . ? C2 H2 0.9300 . ? C3 C4 1.390(5) . ? C3 H3 0.9300 . ? C4 C5 1.382(5) . ? C4 N2 1.415(4) . ? C5 C6 1.377(6) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? N1 C7 1.474(6) . ? N1 C8 1.482(6) . ? N2 C10 1.453(5) . ? N2 C9 1.476(5) . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? 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 C11A I1 C11B 8.6(6) . . ? C18A I2 C18B 9.3(6) . . ? F2A C11A F1A 111.0(10) . . ? F2A C11A C12A 102.9(11) . . ? F1A C11A C12A 106.5(9) . . ? F2A C11A I1 114.0(10) . . ? F1A C11A I1 108.7(7) . . ? C12A C11A I1 113.4(7) . . ? F3A C12A F4A 103.9(10) . . ? F3A C12A C11A 106.0(13) . . ? F4A C12A C11A 108.9(11) . . ? F3A C12A C13A 100.0(10) . . ? F4A C12A C13A 119.9(11) . . ? C11A C12A C13A 116.0(8) . . ? F6A C13A F5A 106.4(10) . . ? F6A C13A C14A 106.5(8) . . ? F5A C13A C14A 106.9(9) . . ? F6A C13A C12A 107.5(9) . . ? F5A C13A C12A 113.3(8) . . ? C14A C13A C12A 115.7(9) . . ? F8A C14A F7A 106.8(10) . . ? F8A C14A C13A 107.1(9) . . ? F7A C14A C13A 101.4(9) . . ? F8A C14A C15A 108.4(8) . . ? F7A C14A C15A 115.4(12) . . ? C13A C14A C15A 117.1(9) . . ? F10A C15A F9A 105.2(10) . . ? F10A C15A C16A 110.8(9) . . ? F9A C15A C16A 110.9(9) . . ? F10A C15A C14A 104.6(8) . . ? F9A C15A C14A 100.9(9) . . ? C16A C15A C14A 122.8(9) . . ? F11A C16A F12A 108.5(10) . . ? F11A C16A C15A 110.0(9) . . ? F12A C16A C15A 107.1(9) . . ? F11A C16A C17A 109.2(10) . . ? F12A C16A C17A 107.4(11) . . ? C15A C16A C17A 114.3(9) . . ? F14A C17A F13A 107.6(11) . . ? F14A C17A C18A 108.3(15) . . ? F13A C17A C18A 110.6(14) . . ? F14A C17A C16A 109.2(16) . . ? F13A C17A C16A 104.6(14) . . ? C18A C17A C16A 116.1(10) . . ? F15A C18A F16A 107.5(8) . . ? F15A C18A C17A 106.7(11) . . ? F16A C18A C17A 105.3(12) . . ? F15A C18A I2 112.4(7) . . ? F16A C18A I2 113.2(8) . . ? C17A C18A I2 111.3(8) . . ? F15B C18B F16B 106.9(10) . . ? F15B C18B C17B 110.5(11) . . ? F16B C18B C17B 110.9(12) . . ? F15B C18B I2 107.3(8) . . ? F16B C18B I2 105.8(9) . . ? C17B C18B I2 115.0(8) . . ? F14B C17B F13B 112.3(10) . . ? F14B C17B C18B 106.7(13) . . ? F13B C17B C18B 105.7(14) . . ? F14B C17B C16B 106.7(14) . . ? F13B C17B C16B 109.6(15) . . ? C18B C17B C16B 115.9(9) . . ? F11B C16B F12B 104.7(8) . . ? F11B C16B C17B 109.8(10) . . ? F12B C16B C17B 106.8(10) . . ? F11B C16B C15B 112.1(9) . . ? F12B C16B C15B 109.1(8) . . ? C17B C16B C15B 113.8(8) . . ? F9B C15B F10B 111.9(8) . . ? F9B C15B C14B 108.1(9) . . ? F10B C15B C14B 110.3(8) . . ? F9B C15B C16B 107.8(9) . . ? F10B C15B C16B 101.9(8) . . ? C14B C15B C16B 116.7(8) . . ? F7B C14B F8B 107.4(9) . . ? F7B C14B C13B 109.4(10) . . ? F8B C14B C13B 109.4(8) . . ? F7B C14B C15B 103.2(9) . . ? F8B C14B C15B 108.4(8) . . ? C13B C14B C15B 118.5(9) . . ? F6B C13B F5B 105.7(9) . . ? F6B C13B C14B 109.6(9) . . ? F5B C13B C14B 108.4(9) . . ? F6B C13B C12B 108.5(9) . . ? F5B C13B C12B 112.3(9) . . ? C14B C13B C12B 112.1(9) . . ? F3B C12B F4B 107.2(10) . . ? F3B C12B C11B 104.7(11) . . ? F4B C12B C11B 108.8(14) . . ? F3B C12B C13B 101.9(9) . . ? F4B C12B C13B 119.7(12) . . ? C11B C12B C13B 113.1(9) . . ? F2B C11B F1B 109.9(10) . . ? F2B C11B C12B 108.3(11) . . ? F1B C11B C12B 101.1(10) . . ? F2B C11B I1 109.2(10) . . ? F1B C11B I1 111.8(8) . . ? C12B C11B I1 116.2(9) . . ? C6 C1 C2 115.3(3) . . ? C6 C1 N1 122.3(3) . . ? C2 C1 N1 122.3(3) . . ? C3 C2 C1 122.3(3) . . ? C3 C2 H2 118.9 . . ? C1 C2 H2 118.9 . . ? C2 C3 C4 122.0(3) . . ? C2 C3 H3 119.0 . . ? C4 C3 H3 119.0 . . ? C5 C4 C3 115.6(3) . . ? C5 C4 N2 122.7(3) . . ? C3 C4 N2 121.6(3) . . ? C6 C5 C4 122.7(3) . . ? C6 C5 H5 118.7 . . ? C4 C5 H5 118.7 . . ? C5 C6 C1 122.1(3) . . ? C5 C6 H6 118.9 . . ? C1 C6 H6 118.9 . . ? C1 N1 C7 115.9(3) . . ? C1 N1 C8 115.7(3) . . ? C7 N1 C8 112.8(4) . . ? C4 N2 C10 116.5(3) . . ? C4 N2 C9 115.7(3) . . ? C10 N2 C9 112.1(3) . . ? N1 C7 H7A 109.5 . . ? N1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? N1 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N1 C8 H8A 109.5 . . ? N1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N2 C9 H9A 109.5 . . ? N2 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N2 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N2 C10 H10A 109.5 . . ? N2 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? N2 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C11B I1 C11A F2A -179(100) . . . . ? C11B I1 C11A F1A -55(4) . . . . ? C11B I1 C11A C12A 63(4) . . . . ? F2A C11A C12A F3A -51.4(11) . . . . ? F1A C11A C12A F3A -168.2(10) . . . . ? I1 C11A C12A F3A 72.2(11) . . . . ? F2A C11A C12A F4A -162.6(12) . . . . ? F1A C11A C12A F4A 80.5(12) . . . . ? I1 C11A C12A F4A -39.0(13) . . . . ? F2A C11A C12A C13A 58.5(14) . . . . ? F1A C11A C12A C13A -58.3(13) . . . . ? I1 C11A C12A C13A -177.9(8) . . . . ? F3A C12A C13A F6A 36.8(13) . . . . ? F4A C12A C13A F6A 149.3(13) . . . . ? C11A C12A C13A F6A -76.6(13) . . . . ? F3A C12A C13A F5A 154.1(12) . . . . ? F4A C12A C13A F5A -93.4(15) . . . . ? C11A C12A C13A F5A 40.8(15) . . . . ? F3A C12A C13A C14A -81.9(13) . . . . ? F4A C12A C13A C14A 30.6(17) . . . . ? C11A C12A C13A C14A 164.7(11) . . . . ? F6A C13A C14A F8A 167.9(9) . . . . ? F5A C13A C14A F8A 54.4(11) . . . . ? C12A C13A C14A F8A -72.8(12) . . . . ? F6A C13A C14A F7A -80.4(11) . . . . ? F5A C13A C14A F7A 166.1(10) . . . . ? C12A C13A C14A F7A 38.9(13) . . . . ? F6A C13A C14A C15A 46.0(12) . . . . ? F5A C13A C14A C15A -67.4(12) . . . . ? C12A C13A C14A C15A 165.3(10) . . . . ? F8A C14A C15A F10A 161.1(10) . . . . ? F7A C14A C15A F10A 41.4(12) . . . . ? C13A C14A C15A F10A -77.8(11) . . . . ? F8A C14A C15A F9A 52.1(12) . . . . ? F7A C14A C15A F9A -67.6(13) . . . . ? C13A C14A C15A F9A 173.2(10) . . . . ? F8A C14A C15A C16A -71.7(13) . . . . ? F7A C14A C15A C16A 168.6(10) . . . . ? C13A C14A C15A C16A 49.4(14) . . . . ? F10A C15A C16A F11A 53.1(12) . . . . ? F9A C15A C16A F11A 169.5(10) . . . . ? C14A C15A C16A F11A -71.4(13) . . . . ? F10A C15A C16A F12A 170.9(9) . . . . ? F9A C15A C16A F12A -72.7(12) . . . . ? C14A C15A C16A F12A 46.4(13) . . . . ? F10A C15A C16A C17A -70.2(13) . . . . ? F9A C15A C16A C17A 46.2(15) . . . . ? C14A C15A C16A C17A 165.3(11) . . . . ? F11A C16A C17A F14A -73.2(13) . . . . ? F12A C16A C17A F14A 169.3(12) . . . . ? C15A C16A C17A F14A 50.6(15) . . . . ? F11A C16A C17A F13A 171.9(11) . . . . ? F12A C16A C17A F13A 54.4(13) . . . . ? C15A C16A C17A F13A -64.4(14) . . . . ? F11A C16A C17A C18A 49.7(18) . . . . ? F12A C16A C17A C18A -67.9(17) . . . . ? C15A C16A C17A C18A 173.4(12) . . . . ? F14A C17A C18A F15A 68.8(14) . . . . ? F13A C17A C18A F15A -173.5(11) . . . . ? C16A C17A C18A F15A -54.4(17) . . . . ? F14A C17A C18A F16A -177.2(13) . . . . ? F13A C17A C18A F16A -59.5(14) . . . . ? C16A C17A C18A F16A 59.6(17) . . . . ? F14A C17A C18A I2 -54.1(14) . . . . ? F13A C17A C18A I2 63.6(14) . . . . ? C16A C17A C18A I2 -177.4(11) . . . . ? C18B I2 C18A F15A -59(4) . . . . ? C18B I2 C18A F16A 179(5) . . . . ? C18B I2 C18A C17A 61(4) . . . . ? C18A I2 C18B F15B 134(5) . . . . ? C18A I2 C18B F16B 20(4) . . . . ? C18A I2 C18B C17B -103(4) . . . . ? F15B C18B C17B F14B 61.3(13) . . . . ? F16B C18B C17B F14B 179.7(12) . . . . ? I2 C18B C17B F14B -60.3(14) . . . . ? F15B C18B C17B F13B -179.0(12) . . . . ? F16B C18B C17B F13B -60.6(14) . . . . ? I2 C18B C17B F13B 59.5(15) . . . . ? F15B C18B C17B C16B -57.4(16) . . . . ? F16B C18B C17B C16B 61.0(17) . . . . ? I2 C18B C17B C16B -179.0(10) . . . . ? F14B C17B C16B F11B -169.7(10) . . . . ? F13B C17B C16B F11B 68.5(13) . . . . ? C18B C17B C16B F11B -51.0(17) . . . . ? F14B C17B C16B F12B -56.6(12) . . . . ? F13B C17B C16B F12B -178.5(11) . . . . ? C18B C17B C16B F12B 62.1(15) . . . . ? F14B C17B C16B C15B 63.8(13) . . . . ? F13B C17B C16B C15B -58.1(14) . . . . ? C18B C17B C16B C15B -177.5(12) . . . . ? F11B C16B C15B F9B -163.9(9) . . . . ? F12B C16B C15B F9B 80.6(10) . . . . ? C17B C16B C15B F9B -38.6(14) . . . . ? F11B C16B C15B F10B -46.0(10) . . . . ? F12B C16B C15B F10B -161.6(8) . . . . ? C17B C16B C15B F10B 79.3(11) . . . . ? F11B C16B C15B C14B 74.3(12) . . . . ? F12B C16B C15B C14B -41.3(12) . . . . ? C17B C16B C15B C14B -160.4(11) . . . . ? F9B C15B C14B F7B 65.4(12) . . . . ? F10B C15B C14B F7B -57.2(11) . . . . ? C16B C15B C14B F7B -172.9(10) . . . . ? F9B C15B C14B F8B -48.2(11) . . . . ? F10B C15B C14B F8B -170.9(8) . . . . ? C16B C15B C14B F8B 73.4(11) . . . . ? F9B C15B C14B C13B -173.5(9) . . . . ? F10B C15B C14B C13B 63.8(11) . . . . ? C16B C15B C14B C13B -51.8(13) . . . . ? F7B C14B C13B F6B 76.1(11) . . . . ? F8B C14B C13B F6B -166.6(8) . . . . ? C15B C14B C13B F6B -41.8(13) . . . . ? F7B C14B C13B F5B -169.0(9) . . . . ? F8B C14B C13B F5B -51.7(11) . . . . ? C15B C14B C13B F5B 73.1(12) . . . . ? F7B C14B C13B C12B -44.5(12) . . . . ? F8B C14B C13B C12B 72.9(10) . . . . ? C15B C14B C13B C12B -162.4(9) . . . . ? F6B C13B C12B F3B -42.1(12) . . . . ? F5B C13B C12B F3B -158.5(10) . . . . ? C14B C13B C12B F3B 79.1(11) . . . . ? F6B C13B C12B F4B -160.0(13) . . . . ? F5B C13B C12B F4B 83.6(15) . . . . ? C14B C13B C12B F4B -38.8(15) . . . . ? F6B C13B C12B C11B 69.8(11) . . . . ? F5B C13B C12B C11B -46.7(13) . . . . ? C14B C13B C12B C11B -169.1(9) . . . . ? F3B C12B C11B F2B 169.7(10) . . . . ? F4B C12B C11B F2B -76.0(14) . . . . ? C13B C12B C11B F2B 59.6(13) . . . . ? F3B C12B C11B F1B 54.2(11) . . . . ? F4B C12B C11B F1B 168.5(11) . . . . ? C13B C12B C11B F1B -55.9(12) . . . . ? F3B C12B C11B I1 -67.1(11) . . . . ? F4B C12B C11B I1 47.3(13) . . . . ? C13B C12B C11B I1 -177.1(7) . . . . ? C11A I1 C11B F2B 19(4) . . . . ? C11A I1 C11B F1B 141(5) . . . . ? C11A I1 C11B C12B -104(5) . . . . ? C6 C1 C2 C3 0.5(5) . . . . ? N1 C1 C2 C3 176.6(4) . . . . ? C1 C2 C3 C4 -0.4(6) . . . . ? C2 C3 C4 C5 0.3(5) . . . . ? C2 C3 C4 N2 176.6(4) . . . . ? C3 C4 C5 C6 -0.3(6) . . . . ? N2 C4 C5 C6 -176.5(4) . . . . ? C4 C5 C6 C1 0.4(7) . . . . ? C2 C1 C6 C5 -0.5(6) . . . . ? N1 C1 C6 C5 -176.6(4) . . . . ? C6 C1 N1 C7 -23.7(5) . . . . ? C2 C1 N1 C7 160.5(4) . . . . ? C6 C1 N1 C8 -159.1(4) . . . . ? C2 C1 N1 C8 25.1(5) . . . . ? C5 C4 N2 C10 -19.6(5) . . . . ? C3 C4 N2 C10 164.4(4) . . . . ? C5 C4 N2 C9 -154.6(4) . . . . ? C3 C4 N2 C9 29.4(5) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 32.02 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.105 _refine_diff_density_min -0.439 _refine_diff_density_rms 0.105 data_re24n1 _database_code_depnum_ccdc_archive 'CCDC 259450' _audit_creation_method SHELXL-97 _chemical_name_systematic ; N,N,N',N'-tetramethyl-p-phenylenediamine.1,8-diiodioperfluorooctane ; _chemical_name_common ; N,N,N',N'-tetramethyl-p-phenylenediamine.1,8- diiodioperfluorooctane ; _chemical_formula_moiety '(C10 H16 N2), (C8 F16 I2)' _chemical_formula_sum 'C18 H16 F16 I2 N2' _chemical_formula_weight 818.13 _chemical_absolute_configuration ad 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' 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 6.1995(10) _cell_length_b 19.159(3) _cell_length_c 21.862(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2596.7(7) _cell_formula_units_Z 4 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 5237 _cell_measurement_theta_min 4.642 _cell_measurement_theta_max 52.901 _exptl_crystal_description 'irregular prism' _exptl_crystal_colour yellow _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.13 _exptl_crystal_density_diffrn 2.093 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1552 _exptl_absorpt_coefficient_mu 2.548 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Bruker, 1997)' _exptl_absorpt_correction_T_min 0.788881 _exptl_absorpt_correction_T_max 1.000000 _exptl_special_details ; These data correspond to the enantiomorph of CCDC 256351, and are deposited on request of the crystallographic referee of the paper accepted for publication in CHEMICAL COMMUNICATION (2005): - Spontaneus resolution in a halogen bonded supramolecular architecture - by H. Neukirch, E. Guido, R. Liantonio, P. Metrangolo, T. Pilati and G. Resnati This data collection was carried out on a fragment of a millimetric crystal, with the only aim to determine the chiral conformation of the crystal and then to use this piece of information for other experiments. For this reason the crystal was cut and not reduced with chloroform as for CCDC 256351. Consequently, the crystal diffraction data were not particularly good and were reduced with respect to CCDC 256351, so that the results of the analysis are of inferior quality. ; _diffrn_ambient_temperature 291(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX' _diffrn_measurement_method '\w scans' _diffrn_standards_decay_% 0.00 _diffrn_reflns_number 43526 _diffrn_reflns_av_R_equivalents 0.0544 _diffrn_reflns_av_sigmaI/netI 0.0502 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.41 _diffrn_reflns_theta_max 27.57 _reflns_number_total 5977 _reflns_number_gt 4811 _reflns_threshold_expression >2\s(I) _computing_data_collection 'SMART (Bruker, 1995)' _computing_cell_refinement 'SAINT, (Bruker 1997)' _computing_data_reduction 'SAINT, (Bruker 1997)' _computing_structure_solution 'SIR-92, (Altomare et al, 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPIII (Burnett & Johnson,1996)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0271P)^2^+2.6187P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.01(3) _refine_ls_number_reflns 5977 _refine_ls_number_parameters 559 _refine_ls_number_restraints 1384 _refine_ls_R_factor_all 0.0568 _refine_ls_R_factor_gt 0.0400 _refine_ls_wR_factor_ref 0.0992 _refine_ls_wR_factor_gt 0.0900 _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_restrained_S_all 1.022 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I1 I 0.44866(7) 1.156889(18) 0.86863(2) 0.06741(13) Uani 1 d D . . I2 I 1.52665(7) 0.618713(17) 0.845064(18) 0.06227(12) Uani 1 d D . . C11A C 0.652(2) 1.0693(7) 0.8457(8) 0.071(4) Uani 0.50 d PDU A 1 C12A C 0.720(3) 1.0273(9) 0.9012(8) 0.075(3) Uani 0.50 d PDU A 1 C13A C 0.871(2) 0.9618(7) 0.8848(6) 0.077(3) Uani 0.50 d PDU A 1 C14A C 0.890(2) 0.9088(7) 0.9374(7) 0.083(4) Uani 0.50 d PDU A 1 C15A C 1.071(2) 0.8552(6) 0.9338(6) 0.078(3) Uani 0.50 d PDU A 1 C16A C 1.100(2) 0.8109(7) 0.8746(6) 0.068(3) Uani 0.50 d PDU A 1 C17A C 1.255(4) 0.7459(10) 0.8847(7) 0.060(3) Uani 0.50 d PDU A 1 C18A C 1.302(2) 0.7032(6) 0.8269(7) 0.060(3) Uani 0.50 d PDU A 1 F16A F 1.1133(19) 0.6806(8) 0.8047(7) 0.079(4) Uani 0.50 d PDU A 1 F15A F 1.387(2) 0.7468(8) 0.7855(7) 0.086(4) Uani 0.50 d PDU A 1 F14A F 1.441(4) 0.7685(14) 0.9093(10) 0.072(4) Uani 0.50 d PDU A 1 F13A F 1.156(4) 0.7053(14) 0.9258(8) 0.063(3) Uani 0.50 d PDU A 1 F12A F 0.9064(17) 0.7861(6) 0.8583(6) 0.102(4) Uani 0.50 d PDU A 1 F11A F 1.175(2) 0.8492(6) 0.8279(4) 0.097(3) Uani 0.50 d PDU A 1 F10A F 1.2547(14) 0.8887(5) 0.9438(5) 0.097(3) Uani 0.50 d PDU A 1 F9A F 1.032(3) 0.8137(6) 0.9811(6) 0.113(4) Uani 0.50 d PDU A 1 F8A F 0.6979(15) 0.8779(6) 0.9433(6) 0.128(4) Uani 0.50 d PDU A 1 F7A F 0.923(3) 0.9499(9) 0.9860(7) 0.090(4) Uani 0.50 d PDU A 1 F6A F 1.0685(16) 0.9847(5) 0.8709(5) 0.102(3) Uani 0.50 d PDU A 1 F5A F 0.798(2) 0.9259(6) 0.8352(5) 0.100(3) Uani 0.50 d PDU A 1 F4A F 0.564(3) 1.0236(10) 0.9447(9) 0.128(7) Uani 0.50 d PDU A 1 F3A F 0.876(3) 1.0698(12) 0.9243(11) 0.089(5) Uani 0.50 d PDU A 1 F2A F 0.836(3) 1.0879(9) 0.8186(9) 0.091(5) Uani 0.50 d PDU A 1 F1A F 0.542(2) 1.0258(6) 0.8091(5) 0.090(4) Uani 0.50 d PDU A 1 C18B C 1.351(2) 0.7142(7) 0.8280(8) 0.070(4) Uani 0.50 d PDU A 2 C17B C 1.252(4) 0.7445(10) 0.8864(8) 0.059(3) Uani 0.50 d PDU A 2 C16B C 1.127(2) 0.8151(8) 0.8765(6) 0.067(3) Uani 0.50 d PDU A 2 C15B C 1.024(2) 0.8466(7) 0.9360(6) 0.081(3) Uani 0.50 d PDU A 2 C14B C 0.956(2) 0.9238(7) 0.9410(6) 0.075(3) Uani 0.50 d PDU A 2 C13B C 0.822(2) 0.9519(7) 0.8875(6) 0.073(3) Uani 0.50 d PDU A 2 C12B C 0.717(3) 1.0256(9) 0.9035(8) 0.074(3) Uani 0.50 d PDU A 2 C11B C 0.612(2) 1.0592(7) 0.8491(9) 0.074(4) Uani 0.50 d PDU A 2 F16B F 1.193(2) 0.6987(9) 0.7889(7) 0.098(4) Uani 0.50 d PDU A 2 F15B F 1.482(2) 0.7601(8) 0.8015(7) 0.093(4) Uani 0.50 d PDU A 2 F14B F 1.415(4) 0.7563(14) 0.9247(10) 0.069(4) Uani 0.50 d PDU A 2 F13B F 1.118(4) 0.6972(15) 0.9100(9) 0.080(5) Uani 0.50 d PDU A 2 F12B F 1.2712(15) 0.8629(5) 0.8575(5) 0.084(3) Uani 0.50 d PDU A 2 F11B F 0.9787(18) 0.8077(5) 0.8330(4) 0.077(3) Uani 0.50 d PDU A 2 F10B F 0.8482(13) 0.8069(4) 0.9456(4) 0.081(2) Uani 0.50 d PDU A 2 F9B F 1.1576(18) 0.8365(7) 0.9831(5) 0.095(3) Uani 0.50 d PDU A 2 F8B F 1.1362(15) 0.9616(5) 0.9440(5) 0.106(3) Uani 0.50 d PDU A 2 F7B F 0.843(3) 0.9325(10) 0.9923(7) 0.093(5) Uani 0.50 d PDU A 2 F6B F 0.6630(13) 0.9057(4) 0.8755(6) 0.096(3) Uani 0.50 d PDU A 2 F5B F 0.9472(18) 0.9557(5) 0.8376(4) 0.078(2) Uani 0.50 d PDU A 2 F4B F 0.830(3) 1.0723(13) 0.9372(10) 0.104(6) Uani 0.50 d PDU A 2 F3B F 0.543(3) 1.0062(8) 0.9357(9) 0.079(3) Uani 0.50 d PDU A 2 F2B F 0.765(3) 1.0693(10) 0.8077(9) 0.099(5) Uani 0.50 d PDU A 2 F1B F 0.474(2) 1.0089(8) 0.8314(7) 0.105(5) Uani 0.50 d PDU A 2 C1 C 0.3376(9) 1.3348(3) 0.8728(2) 0.0495(11) Uani 1 d . . . C2 C 0.4029(11) 1.3612(3) 0.8166(2) 0.0627(16) Uani 1 d . . . H2 H 0.3404 1.3438 0.7811 0.075 Uiso 1 calc R . . C3 C 0.5578(11) 1.4126(3) 0.8121(2) 0.0605(14) Uani 1 d . . . H3 H 0.5991 1.4280 0.7734 0.073 Uiso 1 calc R . . C4 C 0.6542(9) 1.4422(3) 0.8632(2) 0.0496(12) Uani 1 d . . . C5 C 0.5860(11) 1.4158(3) 0.9187(2) 0.0645(16) Uani 1 d . . . H5 H 0.6460 1.4337 0.9544 0.077 Uiso 1 calc R . . C6 C 0.4339(12) 1.3645(3) 0.9231(2) 0.0692(17) Uani 1 d . . . H6 H 0.3937 1.3490 0.9618 0.083 Uiso 1 calc R . . N1 N 0.1895(8) 1.2785(3) 0.8770(3) 0.0603(12) Uani 1 d . . . N2 N 0.8023(8) 1.4983(2) 0.8580(2) 0.0553(11) Uani 1 d . . . C7 C 0.0755(15) 1.2723(4) 0.9366(4) 0.093(2) Uani 1 d . . . H7A H -0.0202 1.2329 0.9354 0.139 Uiso 1 calc R . . H7B H -0.0062 1.3140 0.9440 0.139 Uiso 1 calc R . . H7C H 0.1791 1.2660 0.9687 0.139 Uiso 1 calc R . . C8 C 0.0430(14) 1.2692(4) 0.8248(4) 0.096(2) Uani 1 d . . . H8A H -0.0505 1.2302 0.8324 0.144 Uiso 1 calc R . . H8B H 0.1258 1.2606 0.7884 0.144 Uiso 1 calc R . . H8C H -0.0420 1.3106 0.8194 0.144 Uiso 1 calc R . . C9 C 0.9263(13) 1.5009(4) 0.8008(3) 0.080(2) Uani 1 d . . . H9A H 1.0211 1.5405 0.8015 0.120 Uiso 1 calc R . . H9B H 0.8291 1.5049 0.7668 0.120 Uiso 1 calc R . . H9C H 1.0097 1.4589 0.7967 0.120 Uiso 1 calc R . . C10 C 0.9341(13) 1.5120(4) 0.9119(3) 0.085(2) Uani 1 d . . . H10A H 1.0283 1.5508 0.9039 0.128 Uiso 1 calc R . . H10B H 1.0186 1.4715 0.9213 0.128 Uiso 1 calc R . . H10C H 0.8423 1.5230 0.9459 0.128 Uiso 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I1 0.0707(3) 0.04701(18) 0.0845(3) -0.00007(17) 0.0019(2) 0.01047(19) I2 0.0659(2) 0.04896(18) 0.0720(2) 0.00152(16) 0.0008(2) 0.01029(17) C11A 0.083(8) 0.055(6) 0.074(7) -0.004(6) 0.012(7) 0.004(6) C12A 0.077(7) 0.069(6) 0.077(7) 0.000(6) 0.001(6) -0.001(6) C13A 0.079(7) 0.074(7) 0.079(7) 0.005(6) -0.008(6) 0.007(6) C14A 0.093(7) 0.074(7) 0.082(6) -0.002(6) 0.001(6) -0.004(6) C15A 0.086(7) 0.057(6) 0.092(6) -0.001(6) 0.009(6) 0.011(6) C16A 0.071(6) 0.049(6) 0.084(6) 0.001(6) 0.004(6) 0.016(6) C17A 0.062(6) 0.046(6) 0.072(6) 0.009(6) 0.002(6) 0.003(6) C18A 0.069(7) 0.047(6) 0.064(7) 0.014(5) 0.003(6) 0.011(6) F16A 0.065(7) 0.074(7) 0.097(9) -0.017(6) -0.033(6) 0.008(5) F15A 0.106(10) 0.075(7) 0.078(7) 0.018(6) 0.026(7) 0.012(7) F14A 0.069(6) 0.058(8) 0.088(12) 0.003(8) -0.012(8) -0.004(5) F13A 0.075(8) 0.063(9) 0.051(7) 0.006(6) 0.004(6) -0.003(6) F12A 0.074(6) 0.072(7) 0.159(11) -0.022(7) -0.038(7) 0.010(5) F11A 0.143(10) 0.074(6) 0.075(6) 0.020(5) 0.002(5) 0.042(7) F10A 0.085(6) 0.081(5) 0.124(7) -0.028(6) -0.027(5) 0.015(5) F9A 0.172(13) 0.091(7) 0.077(6) 0.022(6) 0.042(9) 0.024(8) F8A 0.075(6) 0.126(8) 0.182(10) 0.014(8) 0.028(6) -0.015(6) F7A 0.114(10) 0.096(9) 0.059(7) -0.019(7) 0.009(6) 0.012(7) F6A 0.090(7) 0.078(5) 0.138(8) 0.020(6) 0.041(7) 0.004(5) F5A 0.121(8) 0.099(7) 0.079(6) -0.035(6) -0.040(6) 0.045(6) F4A 0.138(12) 0.144(14) 0.103(10) 0.067(10) 0.023(9) 0.046(11) F3A 0.079(7) 0.071(7) 0.115(12) -0.029(7) -0.003(6) 0.006(6) F2A 0.099(10) 0.057(6) 0.116(11) 0.020(6) 0.044(8) 0.005(5) F1A 0.136(12) 0.060(7) 0.075(6) -0.017(5) -0.037(7) 0.019(7) C18B 0.079(8) 0.053(7) 0.077(7) 0.004(6) -0.003(7) 0.015(6) C17B 0.061(6) 0.047(6) 0.069(6) 0.008(6) 0.002(6) 0.005(6) C16B 0.069(6) 0.054(6) 0.080(6) 0.002(6) -0.003(6) 0.013(6) C15B 0.087(7) 0.070(6) 0.085(6) 0.000(6) -0.001(6) 0.016(6) C14B 0.091(7) 0.064(6) 0.070(6) 0.002(5) 0.005(6) 0.013(6) C13B 0.084(7) 0.061(6) 0.074(6) 0.011(6) 0.009(6) 0.006(6) C12B 0.076(7) 0.069(6) 0.077(7) 0.004(6) 0.003(6) -0.003(6) C11B 0.072(7) 0.070(7) 0.080(7) 0.006(7) 0.005(7) 0.010(6) F16B 0.108(12) 0.107(11) 0.078(8) -0.013(7) -0.033(8) 0.032(8) F15B 0.104(11) 0.072(7) 0.103(9) 0.034(6) 0.026(7) 0.017(7) F14B 0.076(9) 0.067(10) 0.063(8) 0.013(5) -0.017(6) 0.006(6) F13B 0.094(10) 0.055(6) 0.091(13) 0.003(9) 0.001(8) -0.013(6) F12B 0.081(6) 0.052(4) 0.120(8) 0.015(5) 0.035(5) -0.002(4) F11B 0.092(8) 0.075(6) 0.064(5) 0.011(4) -0.013(5) 0.021(5) F10B 0.085(6) 0.075(5) 0.082(5) 0.018(4) 0.019(4) 0.017(4) F9B 0.117(9) 0.100(8) 0.069(6) -0.015(6) -0.028(6) 0.028(7) F8B 0.096(7) 0.090(6) 0.132(8) -0.027(6) -0.029(6) -0.014(5) F7B 0.128(12) 0.103(10) 0.048(5) 0.015(5) 0.030(7) 0.030(8) F6B 0.071(5) 0.072(5) 0.145(8) -0.010(6) -0.029(6) -0.001(4) F5B 0.103(7) 0.076(5) 0.053(4) 0.016(4) 0.029(5) 0.032(5) F4B 0.127(13) 0.101(9) 0.085(9) -0.036(7) -0.056(10) 0.032(9) F3B 0.079(6) 0.058(4) 0.100(7) 0.004(4) 0.046(6) 0.001(4) F2B 0.101(11) 0.111(13) 0.084(7) 0.009(8) 0.032(8) 0.034(8) F1B 0.091(7) 0.068(7) 0.155(13) -0.028(8) -0.019(9) -0.005(5) C1 0.055(3) 0.042(3) 0.051(3) -0.002(2) 0.001(2) 0.009(2) C2 0.085(4) 0.058(3) 0.045(3) -0.002(2) -0.007(3) -0.002(3) C3 0.078(4) 0.061(3) 0.042(3) 0.001(2) -0.001(3) -0.002(3) C4 0.056(3) 0.044(3) 0.049(3) 0.001(2) 0.004(2) 0.013(2) C5 0.085(4) 0.064(3) 0.045(3) -0.009(2) -0.002(3) -0.004(3) C6 0.097(5) 0.068(3) 0.043(3) 0.004(2) 0.006(3) -0.011(4) N1 0.059(3) 0.051(2) 0.071(3) 0.000(2) 0.000(2) 0.006(2) N2 0.059(3) 0.048(2) 0.059(3) -0.002(2) 0.003(2) 0.005(2) C7 0.097(6) 0.077(4) 0.104(5) 0.002(4) 0.036(5) -0.024(4) C8 0.080(5) 0.081(5) 0.127(6) 0.018(4) -0.043(5) -0.006(4) C9 0.081(5) 0.075(4) 0.084(4) 0.002(3) 0.028(4) -0.005(4) C10 0.079(5) 0.076(4) 0.100(5) 0.001(4) -0.017(4) 0.001(4) _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 C11A 2.158(11) . NO I1 C11B 2.169(12) . NO I2 C18B 2.160(12) . NO I2 C18A 2.171(10) . NO C11A F2A 1.335(12) . NO C11A F1A 1.343(12) . NO C11A C12A 1.514(12) . NO C12A F4A 1.356(12) . NO C12A F3A 1.362(12) . NO C12A C13A 1.607(12) . NO C13A F6A 1.337(12) . NO C13A F5A 1.360(12) . NO C13A C14A 1.538(13) . NO C14A F8A 1.336(12) . NO C14A F7A 1.339(12) . NO C14A C15A 1.522(13) . NO C15A F9A 1.326(11) . NO C15A F10A 1.328(12) . NO C15A C16A 1.558(12) . NO C16A F12A 1.337(12) . NO C16A F11A 1.341(11) . NO C16A C17A 1.591(12) . NO C17A F13A 1.338(11) . NO C17A F14A 1.343(11) . NO C17A C18A 1.532(12) . NO C18A F16A 1.339(12) . NO C18A F15A 1.339(11) . NO C18B F15B 1.331(12) . NO C18B F16B 1.335(12) . NO C18B C17B 1.530(13) . NO C17B F14B 1.330(11) . NO C17B F13B 1.333(11) . NO C17B C16B 1.575(12) . NO C16B F11B 1.330(11) . NO C16B F12B 1.346(12) . NO C16B C15B 1.571(13) . NO C15B F9B 1.336(11) . NO C15B F10B 1.343(12) . NO C15B C14B 1.542(15) . NO C14B F7B 1.332(11) . NO C14B F8B 1.333(11) . NO C14B C13B 1.533(13) . NO C13B F5B 1.342(11) . NO C13B F6B 1.351(12) . NO C13B C12B 1.593(13) . NO C12B F3B 1.341(12) . NO C12B F4B 1.352(12) . NO C12B C11B 1.503(13) . NO C11B F2B 1.328(12) . NO C11B F1B 1.346(12) . NO C1 C6 1.374(8) . NO C1 C2 1.390(8) . NO C1 N1 1.419(7) . NO C2 C3 1.379(9) . NO C2 H2 0.9300 . NO C3 C4 1.390(8) . NO C3 H3 0.9300 . NO C4 C5 1.380(8) . NO C4 N2 1.418(7) . NO C5 C6 1.366(9) . NO C5 H5 0.9300 . NO C6 H6 0.9300 . NO N1 C8 1.471(9) . NO N1 C7 1.486(9) . NO N2 C10 1.459(9) . NO N2 C9 1.467(8) . NO C7 H7A 0.9600 . NO C7 H7B 0.9600 . NO C7 H7C 0.9600 . NO C8 H8A 0.9600 . NO C8 H8B 0.9600 . NO C8 H8C 0.9600 . NO C9 H9A 0.9600 . NO C9 H9B 0.9600 . NO C9 H9C 0.9600 . NO C10 H10A 0.9600 . NO C10 H10B 0.9600 . NO C10 H10C 0.9600 . NO loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C11A I1 C11B 8.6(8) . . NO C18B I2 C18A 9.8(7) . . NO F2A C11A F1A 109.6(11) . . NO F2A C11A C12A 105.1(14) . . NO F1A C11A C12A 106.8(13) . . NO F2A C11A I1 113.3(12) . . NO F1A C11A I1 108.9(10) . . NO C12A C11A I1 112.9(10) . . NO F4A C12A F3A 106.0(11) . . NO F4A C12A C11A 113.1(15) . . NO F3A C12A C11A 100.1(18) . . NO F4A C12A C13A 122.0(15) . . NO F3A C12A C13A 97.8(16) . . NO C11A C12A C13A 113.5(10) . . NO F6A C13A F5A 106.7(11) . . NO F6A C13A C14A 108.5(10) . . NO F5A C13A C14A 106.7(11) . . NO F6A C13A C12A 109.2(12) . . NO F5A C13A C12A 112.3(10) . . NO C14A C13A C12A 113.2(10) . . NO F8A C14A F7A 108.6(11) . . NO F8A C14A C15A 111.2(11) . . NO F7A C14A C15A 109.0(14) . . NO F8A C14A C13A 107.2(12) . . NO F7A C14A C13A 102.6(12) . . NO C15A C14A C13A 117.7(10) . . NO F9A C15A F10A 108.5(11) . . NO F9A C15A C14A 103.3(12) . . NO F10A C15A C14A 107.3(10) . . NO F9A C15A C16A 110.1(10) . . NO F10A C15A C16A 107.5(11) . . NO C14A C15A C16A 119.6(10) . . NO F12A C16A F11A 107.8(11) . . NO F12A C16A C15A 108.2(11) . . NO F11A C16A C15A 112.1(11) . . NO F12A C16A C17A 107.5(13) . . NO F11A C16A C17A 108.8(12) . . NO C15A C16A C17A 112.4(10) . . NO F13A C17A F14A 108.1(11) . . NO F13A C17A C18A 109.3(17) . . NO F14A C17A C18A 109.9(19) . . NO F13A C17A C16A 105.8(19) . . NO F14A C17A C16A 108.7(19) . . NO C18A C17A C16A 114.8(10) . . NO F16A C18A F15A 107.3(10) . . NO F16A C18A C17A 107.8(14) . . NO F15A C18A C17A 107.4(14) . . NO F16A C18A I2 112.7(10) . . NO F15A C18A I2 109.7(10) . . NO C17A C18A I2 111.7(9) . . NO F15B C18B F16B 108.5(11) . . NO F15B C18B C17B 110.9(15) . . NO F16B C18B C17B 108.9(15) . . NO F15B C18B I2 109.1(11) . . NO F16B C18B I2 107.0(11) . . NO C17B C18B I2 112.3(10) . . NO F14B C17B F13B 110.1(11) . . NO F14B C17B C18B 107(2) . . NO F13B C17B C18B 108.4(19) . . NO F14B C17B C16B 108.3(19) . . NO F13B C17B C16B 109(2) . . NO C18B C17B C16B 114.1(12) . . NO F11B C16B F12B 108.1(11) . . NO F11B C16B C15B 110.5(12) . . NO F12B C16B C15B 105.3(11) . . NO F11B C16B C17B 110.4(13) . . NO F12B C16B C17B 107.5(14) . . NO C15B C16B C17B 114.7(11) . . NO F9B C15B F10B 107.6(11) . . NO F9B C15B C14B 104.6(12) . . NO F10B C15B C14B 108.2(11) . . NO F9B C15B C16B 109.2(12) . . NO F10B C15B C16B 104.0(11) . . NO C14B C15B C16B 122.6(11) . . NO F7B C14B F8B 109.3(11) . . NO F7B C14B C13B 108.3(13) . . NO F8B C14B C13B 107.5(11) . . NO F7B C14B C15B 108.8(14) . . NO F8B C14B C15B 107.3(11) . . NO C13B C14B C15B 115.5(11) . . NO F5B C13B F6B 107.4(11) . . NO F5B C13B C14B 109.1(11) . . NO F6B C13B C14B 108.3(11) . . NO F5B C13B C12B 111.5(11) . . NO F6B C13B C12B 109.1(12) . . NO C14B C13B C12B 111.4(12) . . NO F3B C12B F4B 108.1(11) . . NO F3B C12B C11B 100.5(16) . . NO F4B C12B C11B 111.9(16) . . NO F3B C12B C13B 101.4(13) . . NO F4B C12B C13B 119.7(17) . . NO C11B C12B C13B 112.6(12) . . NO F2B C11B F1B 111.3(12) . . NO F2B C11B C12B 106.8(14) . . NO F1B C11B C12B 101.4(14) . . NO F2B C11B I1 110.1(13) . . NO F1B C11B I1 112.3(11) . . NO C12B C11B I1 114.7(11) . . NO C6 C1 C2 115.5(5) . . NO C6 C1 N1 123.0(5) . . NO C2 C1 N1 121.5(5) . . NO C3 C2 C1 121.8(5) . . NO C3 C2 H2 119.1 . . NO C1 C2 H2 119.1 . . NO C2 C3 C4 122.2(5) . . NO C2 C3 H3 118.9 . . NO C4 C3 H3 118.9 . . NO C5 C4 C3 115.2(5) . . NO C5 C4 N2 123.2(5) . . NO C3 C4 N2 121.5(5) . . NO C6 C5 C4 122.5(5) . . NO C6 C5 H5 118.7 . . NO C4 C5 H5 118.7 . . NO C5 C6 C1 122.8(5) . . NO C5 C6 H6 118.6 . . NO C1 C6 H6 118.6 . . NO C1 N1 C8 116.3(5) . . NO C1 N1 C7 115.2(5) . . NO C8 N1 C7 112.1(6) . . NO C4 N2 C10 115.7(5) . . NO C4 N2 C9 115.7(5) . . NO C10 N2 C9 112.9(6) . . NO N1 C7 H7A 109.5 . . NO N1 C7 H7B 109.5 . . NO H7A C7 H7B 109.5 . . NO N1 C7 H7C 109.5 . . NO H7A C7 H7C 109.5 . . NO H7B C7 H7C 109.5 . . NO N1 C8 H8A 109.5 . . NO N1 C8 H8B 109.5 . . NO H8A C8 H8B 109.5 . . NO N1 C8 H8C 109.5 . . NO H8A C8 H8C 109.5 . . NO H8B C8 H8C 109.5 . . NO N2 C9 H9A 109.5 . . NO N2 C9 H9B 109.5 . . NO H9A C9 H9B 109.5 . . NO N2 C9 H9C 109.5 . . NO H9A C9 H9C 109.5 . . NO H9B C9 H9C 109.5 . . NO N2 C10 H10A 109.5 . . NO N2 C10 H10B 109.5 . . NO H10A C10 H10B 109.5 . . NO N2 C10 H10C 109.5 . . NO H10A C10 H10C 109.5 . . NO H10B C10 H10C 109.5 . . NO 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 C11B I1 C11A F2A 170(7) . . . . NO C11B I1 C11A F1A 47(5) . . . . NO C11B I1 C11A C12A -71(6) . . . . NO F2A C11A C12A F4A 159.4(15) . . . . NO F1A C11A C12A F4A -84.3(16) . . . . NO I1 C11A C12A F4A 35.4(18) . . . . NO F2A C11A C12A F3A 47.0(15) . . . . NO F1A C11A C12A F3A 163.4(13) . . . . NO I1 C11A C12A F3A -77.0(15) . . . . NO F2A C11A C12A C13A -56.1(17) . . . . NO F1A C11A C12A C13A 60.2(18) . . . . NO I1 C11A C12A C13A 179.9(10) . . . . NO F4A C12A C13A F6A -144.8(17) . . . . NO F3A C12A C13A F6A -30.4(16) . . . . NO C11A C12A C13A F6A 74.3(17) . . . . NO F4A C12A C13A F5A 97.1(18) . . . . NO F3A C12A C13A F5A -148.6(16) . . . . NO C11A C12A C13A F5A -43.9(19) . . . . NO F4A C12A C13A C14A -24(2) . . . . NO F3A C12A C13A C14A 90.5(16) . . . . NO C11A C12A C13A C14A -164.8(14) . . . . NO F6A C13A C14A F8A -169.4(11) . . . . NO F5A C13A C14A F8A -54.8(13) . . . . NO C12A C13A C14A F8A 69.2(14) . . . . NO F6A C13A C14A F7A 76.2(13) . . . . NO F5A C13A C14A F7A -169.2(12) . . . . NO C12A C13A C14A F7A -45.1(16) . . . . NO F6A C13A C14A C15A -43.3(15) . . . . NO F5A C13A C14A C15A 71.3(14) . . . . NO C12A C13A C14A C15A -164.7(12) . . . . NO F8A C14A C15A F9A -49.8(15) . . . . NO F7A C14A C15A F9A 69.9(15) . . . . NO C13A C14A C15A F9A -173.9(12) . . . . NO F8A C14A C15A F10A -164.3(13) . . . . NO F7A C14A C15A F10A -44.6(14) . . . . NO C13A C14A C15A F10A 71.5(14) . . . . NO F8A C14A C15A C16A 73.0(15) . . . . NO F7A C14A C15A C16A -167.3(12) . . . . NO C13A C14A C15A C16A -51.1(16) . . . . NO F9A C15A C16A F12A 72.0(14) . . . . NO F10A C15A C16A F12A -169.9(11) . . . . NO C14A C15A C16A F12A -47.4(15) . . . . NO F9A C15A C16A F11A -169.3(13) . . . . NO F10A C15A C16A F11A -51.3(13) . . . . NO C14A C15A C16A F11A 71.3(15) . . . . NO F9A C15A C16A C17A -46.5(18) . . . . NO F10A C15A C16A C17A 71.6(15) . . . . NO C14A C15A C16A C17A -165.9(14) . . . . NO F12A C16A C17A F13A -55.5(15) . . . . NO F11A C16A C17A F13A -171.9(13) . . . . NO C15A C16A C17A F13A 63.4(17) . . . . NO F12A C16A C17A F14A -171.4(15) . . . . NO F11A C16A C17A F14A 72.2(15) . . . . NO C15A C16A C17A F14A -52.5(18) . . . . NO F12A C16A C17A C18A 65(2) . . . . NO F11A C16A C17A C18A -51(2) . . . . NO C15A C16A C17A C18A -176.0(15) . . . . NO F13A C17A C18A F16A 60.3(17) . . . . NO F14A C17A C18A F16A 178.8(14) . . . . NO C16A C17A C18A F16A -58(2) . . . . NO F13A C17A C18A F15A 175.7(15) . . . . NO F14A C17A C18A F15A -65.9(16) . . . . NO C16A C17A C18A F15A 57(2) . . . . NO F13A C17A C18A I2 -64.0(18) . . . . NO F14A C17A C18A I2 54.5(17) . . . . NO C16A C17A C18A I2 177.4(13) . . . . NO C18B I2 C18A F16A 164(6) . . . . NO C18B I2 C18A F15A 44(4) . . . . NO C18B I2 C18A C17A -75(5) . . . . NO C18A I2 C18B F15B -152(6) . . . . NO C18A I2 C18B F16B -34(4) . . . . NO C18A I2 C18B C17B 85(5) . . . . NO F15B C18B C17B F14B -63.2(17) . . . . NO F16B C18B C17B F14B 177.5(15) . . . . NO I2 C18B C17B F14B 59.1(18) . . . . NO F15B C18B C17B F13B 178.2(15) . . . . NO F16B C18B C17B F13B 58.9(18) . . . . NO I2 C18B C17B F13B -59.4(19) . . . . NO F15B C18B C17B C16B 56(2) . . . . NO F16B C18B C17B C16B -63(2) . . . . NO I2 C18B C17B C16B 178.7(13) . . . . NO F14B C17B C16B F11B 172.8(15) . . . . NO F13B C17B C16B F11B -67.3(16) . . . . NO C18B C17B C16B F11B 54(2) . . . . NO F14B C17B C16B F12B 55.1(17) . . . . NO F13B C17B C16B F12B 175.0(14) . . . . NO C18B C17B C16B F12B -64(2) . . . . NO F14B C17B C16B C15B -61.7(19) . . . . NO F13B C17B C16B C15B 58.3(19) . . . . NO C18B C17B C16B C15B 179.7(15) . . . . NO F11B C16B C15B F9B 163.8(12) . . . . NO F12B C16B C15B F9B -79.7(14) . . . . NO C17B C16B C15B F9B 38.3(18) . . . . NO F11B C16B C15B F10B 49.2(13) . . . . NO F12B C16B C15B F10B 165.7(10) . . . . NO C17B C16B C15B F10B -76.3(15) . . . . NO F11B C16B C15B C14B -73.5(15) . . . . NO F12B C16B C15B C14B 43.0(16) . . . . NO C17B C16B C15B C14B 161.0(15) . . . . NO F9B C15B C14B F7B -65.1(16) . . . . NO F10B C15B C14B F7B 49.3(15) . . . . NO C16B C15B C14B F7B 170.1(13) . . . . NO F9B C15B C14B F8B 53.1(14) . . . . NO F10B C15B C14B F8B 167.5(11) . . . . NO C16B C15B C14B F8B -71.7(15) . . . . NO F9B C15B C14B C13B 173.0(11) . . . . NO F10B C15B C14B C13B -72.6(14) . . . . NO C16B C15B C14B C13B 48.2(17) . . . . NO F7B C14B C13B F5B 168.6(12) . . . . NO F8B C14B C13B F5B 50.6(14) . . . . NO C15B C14B C13B F5B -69.2(14) . . . . NO F7B C14B C13B F6B -74.8(14) . . . . NO F8B C14B C13B F6B 167.2(11) . . . . NO C15B C14B C13B F6B 47.4(15) . . . . NO F7B C14B C13B C12B 45.2(16) . . . . NO F8B C14B C13B C12B -72.9(13) . . . . NO C15B C14B C13B C12B 167.4(12) . . . . NO F5B C13B C12B F3B 156.3(15) . . . . NO F6B C13B C12B F3B 37.9(17) . . . . NO C14B C13B C12B F3B -81.6(16) . . . . NO F5B C13B C12B F4B -84.9(18) . . . . NO F6B C13B C12B F4B 156.6(15) . . . . NO C14B C13B C12B F4B 37.1(18) . . . . NO F5B C13B C12B C11B 49.7(18) . . . . NO F6B C13B C12B C11B -68.7(16) . . . . NO C14B C13B C12B C11B 171.8(12) . . . . NO F3B C12B C11B F2B -168.5(13) . . . . NO F4B C12B C11B F2B 77.0(17) . . . . NO C13B C12B C11B F2B -61.3(17) . . . . NO F3B C12B C11B F1B -51.9(14) . . . . NO F4B C12B C11B F1B -166.4(14) . . . . NO C13B C12B C11B F1B 55.3(16) . . . . NO F3B C12B C11B I1 69.3(14) . . . . NO F4B C12B C11B I1 -45.2(17) . . . . NO C13B C12B C11B I1 176.5(10) . . . . NO C11A I1 C11B F2B -27(5) . . . . NO C11A I1 C11B F1B -152(7) . . . . NO C11A I1 C11B C12B 93(6) . . . . NO C6 C1 C2 C3 1.5(9) . . . . NO N1 C1 C2 C3 -175.4(6) . . . . NO C1 C2 C3 C4 -1.6(10) . . . . NO C2 C3 C4 C5 0.9(8) . . . . NO C2 C3 C4 N2 -175.6(6) . . . . NO C3 C4 C5 C6 -0.3(9) . . . . NO N2 C4 C5 C6 176.1(6) . . . . NO C4 C5 C6 C1 0.4(11) . . . . NO C2 C1 C6 C5 -1.0(9) . . . . NO N1 C1 C6 C5 176.0(6) . . . . NO C6 C1 N1 C8 158.4(6) . . . . NO C2 C1 N1 C8 -24.9(8) . . . . NO C6 C1 N1 C7 24.3(8) . . . . NO C2 C1 N1 C7 -159.0(6) . . . . NO C5 C4 N2 C10 19.7(8) . . . . NO C3 C4 N2 C10 -164.1(6) . . . . NO C5 C4 N2 C9 155.0(6) . . . . NO C3 C4 N2 C9 -28.8(8) . . . . NO _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.57 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.869 _refine_diff_density_min -0.344 _refine_diff_density_rms 0.100