# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2006 data_publication_text _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year 2006 _journal_page_first 3290 _publ_contact_author_name 'Duncan W. Bruce' _publ_contact_author_address ;Department of Chemistry, University of York, Heslington, YORK, UK YO10 5DD ; _publ_contact_author_email db519@york.ac.uk _publ_contact_author_phone '+44 1904 434085' _journal_page_last 3292 loop_ _publ_author_name _publ_author_address P.Metrangolo ;NFMLab-DCMIC G. Natta, 7 via Mancinelli, I-20131 Milan, Politecnico di Milano, Italy. ; C.Prasang ;Department of Chemistry, University of York, Heslington, YORK, UK YO10 5DD ; G.Resnati ;NFMLab-DCMIC G. Natta, 7 via Mancinelli, I-20131 Milan, Politecnico di Milano, Italy. ; R.Liantonio ;NFMLab-DCMIC G. Natta, 7 via Mancinelli, I-20131 Milan, Politecnico di Milano, Italy. ; A.C.Whitwood ;Department of Chemistry, University of York, Heslington, YORK, UK YO10 5DD ; D.W.Bruce ;Department of Chemistry, University of York, Heslington, YORK, UK YO10 5DD ; data_dwb0503m _database_code_depnum_ccdc_archive 'CCDC 604155' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H27 N O, 0.5(C6 F12 I2)' _chemical_formula_sum 'C24 H27 F6 I N O' _chemical_formula_weight 586.37 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.9751(4) _cell_length_b 12.3703(6) _cell_length_c 12.7345(6) _cell_angle_alpha 105.8320(10) _cell_angle_beta 97.4870(10) _cell_angle_gamma 96.4920(10) _cell_volume 1183.72(10) _cell_formula_units_Z 2 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 8772 _cell_measurement_theta_min 2.61 _cell_measurement_theta_max 30.01 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.645 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 586 _exptl_absorpt_coefficient_mu 1.417 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.766 _exptl_absorpt_correction_T_max 0.870 _exptl_absorpt_process_details 'SADABS v2.03; (Sheldrick)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13476 _diffrn_reflns_av_R_equivalents 0.0165 _diffrn_reflns_av_sigmaI/netI 0.0255 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.69 _diffrn_reflns_theta_max 30.01 _reflns_number_total 6656 _reflns_number_gt 6211 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker 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 'calc w=1/[\s^2^(Fo^2^)+(0.0345P)^2^+0.2679P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6656 _refine_ls_number_parameters 299 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0259 _refine_ls_R_factor_gt 0.0236 _refine_ls_wR_factor_ref 0.0598 _refine_ls_wR_factor_gt 0.0587 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _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 C1 C -0.1239(2) 0.64049(14) 0.46321(14) 0.0235(3) Uani 1 1 d . . . H1 H -0.1853 0.5671 0.4535 0.028 Uiso 1 1 calc R . . C2 C -0.0872(2) 0.66948(14) 0.37015(14) 0.0218(3) Uani 1 1 d . . . H2 H -0.1230 0.6164 0.2988 0.026 Uiso 1 1 calc R . . C3 C 0.00268(19) 0.77687(13) 0.38129(13) 0.0180(3) Uani 1 1 d . . . C4 C 0.0525(2) 0.84979(14) 0.48952(13) 0.0199(3) Uani 1 1 d . . . H4 H 0.1149 0.9236 0.5022 0.024 Uiso 1 1 calc R . . C5 C 0.0100(2) 0.81356(14) 0.57745(14) 0.0215(3) Uani 1 1 d . . . H5 H 0.0446 0.8643 0.6500 0.026 Uiso 1 1 calc R . . C6 C 0.0402(2) 0.80521(13) 0.28187(13) 0.0193(3) Uani 1 1 d . . . H6 H 0.0011 0.7474 0.2137 0.023 Uiso 1 1 calc R . . C7 C 0.1232(2) 0.90294(14) 0.27535(13) 0.0199(3) Uani 1 1 d . . . H7 H 0.1599 0.9629 0.3422 0.024 Uiso 1 1 calc R . . C8 C 0.1613(2) 0.92412(13) 0.17277(13) 0.0184(3) Uani 1 1 d . . . C9 C 0.1463(2) 0.83548(13) 0.07442(14) 0.0230(3) Uani 1 1 d . . . H9 H 0.1114 0.7594 0.0741 0.028 Uiso 1 1 calc R . . C10 C 0.1813(2) 0.85687(14) -0.02186(14) 0.0240(3) Uani 1 1 d . . . H10 H 0.1694 0.7956 -0.0877 0.029 Uiso 1 1 calc R . . C11 C 0.2339(2) 0.96783(14) -0.02322(13) 0.0199(3) Uani 1 1 d . . . C12 C 0.2529(2) 1.05699(14) 0.07371(13) 0.0234(3) Uani 1 1 d . . . H12 H 0.2904 1.1328 0.0742 0.028 Uiso 1 1 calc R . . C13 C 0.2166(2) 1.03389(14) 0.16989(13) 0.0234(3) Uani 1 1 d . . . H13 H 0.2301 1.0951 0.2359 0.028 Uiso 1 1 calc R . . C14 C 0.3328(2) 1.08824(14) -0.12923(13) 0.0210(3) Uani 1 1 d . . . H14A H 0.4436 1.1172 -0.0785 0.025 Uiso 1 1 calc R . . H14B H 0.2531 1.1433 -0.1088 0.025 Uiso 1 1 calc R . . C15 C 0.3570(2) 1.07125(14) -0.24821(13) 0.0211(3) Uani 1 1 d . . . H15A H 0.2444 1.0424 -0.2969 0.025 Uiso 1 1 calc R . . H15B H 0.4315 1.0125 -0.2678 0.025 Uiso 1 1 calc R . . C16 C 0.4357(2) 1.17911(13) -0.27055(12) 0.0188(3) Uani 1 1 d . . . H16A H 0.5518 1.2056 -0.2260 0.023 Uiso 1 1 calc R . . H16B H 0.3652 1.2396 -0.2476 0.023 Uiso 1 1 calc R . . C17 C 0.4469(2) 1.15821(14) -0.39302(13) 0.0204(3) Uani 1 1 d . . . H17A H 0.5112 1.0943 -0.4161 0.024 Uiso 1 1 calc R . . H17B H 0.3296 1.1348 -0.4364 0.024 Uiso 1 1 calc R . . C18 C 0.5325(2) 1.26048(13) -0.42149(12) 0.0190(3) Uani 1 1 d . . . H18A H 0.6519 1.2820 -0.3813 0.023 Uiso 1 1 calc R . . H18B H 0.4713 1.3256 -0.3962 0.023 Uiso 1 1 calc R . . C19 C 0.5338(2) 1.23681(14) -0.54516(13) 0.0202(3) Uani 1 1 d . . . H19A H 0.5890 1.1688 -0.5708 0.024 Uiso 1 1 calc R . . H19B H 0.4141 1.2189 -0.5846 0.024 Uiso 1 1 calc R . . C20 C 0.6264(2) 1.33465(14) -0.57655(14) 0.0227(3) Uani 1 1 d . . . H20A H 0.7428 1.3578 -0.5320 0.027 Uiso 1 1 calc R . . H20B H 0.5643 1.4005 -0.5584 0.027 Uiso 1 1 calc R . . C21 C 0.6403(2) 1.30355(17) -0.69894(15) 0.0286(4) Uani 1 1 d . . . H21A H 0.7024 1.2387 -0.7173 0.043 Uiso 1 1 calc R . . H21B H 0.7022 1.3687 -0.7149 0.043 Uiso 1 1 calc R . . H21C H 0.5253 1.2832 -0.7435 0.043 Uiso 1 1 calc R . . N1 N -0.07739(18) 0.71057(12) 0.56596(12) 0.0220(3) Uani 1 1 d . . . O1 O 0.26324(16) 0.97859(10) -0.12303(9) 0.0238(2) Uani 1 1 d . . . C22 C -0.1922(2) 0.53593(14) 0.85741(13) 0.0208(3) Uani 1 1 d . . . C23 C -0.3692(2) 0.54747(12) 0.89114(12) 0.0187(3) Uani 1 1 d . . . C24 C -0.4059(2) 0.50163(13) 0.98938(12) 0.0189(3) Uani 1 1 d . . . F1 F -0.17997(15) 0.42412(9) 0.82134(9) 0.0301(2) Uani 1 1 d . . . F2 F -0.07081(14) 0.58231(10) 0.94813(9) 0.0316(2) Uani 1 1 d . . . F3 F -0.48822(13) 0.49294(9) 0.80174(8) 0.0245(2) Uani 1 1 d . . . F4 F -0.38452(14) 0.65848(8) 0.92061(9) 0.0271(2) Uani 1 1 d . . . F5 F -0.36716(15) 0.39615(9) 0.97158(9) 0.0288(2) Uani 1 1 d . . . F6 F -0.30209(14) 0.56991(10) 1.08105(8) 0.0304(2) Uani 1 1 d . . . I1 I -0.147109(12) 0.616125(8) 0.730258(8) 0.02012(4) 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 C1 0.0228(7) 0.0231(7) 0.0268(8) 0.0124(6) 0.0055(6) -0.0012(6) C2 0.0232(7) 0.0209(7) 0.0213(7) 0.0076(6) 0.0032(6) 0.0009(6) C3 0.0168(6) 0.0200(7) 0.0205(7) 0.0101(6) 0.0047(5) 0.0050(5) C4 0.0210(7) 0.0195(7) 0.0212(7) 0.0088(6) 0.0048(6) 0.0034(6) C5 0.0229(7) 0.0234(7) 0.0209(7) 0.0092(6) 0.0064(6) 0.0046(6) C6 0.0214(7) 0.0208(7) 0.0173(7) 0.0079(6) 0.0035(6) 0.0038(6) C7 0.0228(7) 0.0207(7) 0.0183(7) 0.0077(6) 0.0051(6) 0.0050(6) C8 0.0198(7) 0.0200(7) 0.0171(7) 0.0080(5) 0.0040(5) 0.0026(5) C9 0.0311(8) 0.0164(7) 0.0216(7) 0.0060(6) 0.0065(6) 0.0000(6) C10 0.0330(9) 0.0181(7) 0.0191(7) 0.0033(6) 0.0064(6) -0.0001(6) C11 0.0227(7) 0.0219(7) 0.0170(7) 0.0088(6) 0.0044(6) 0.0021(6) C12 0.0339(9) 0.0173(7) 0.0190(7) 0.0067(6) 0.0060(6) -0.0009(6) C13 0.0327(9) 0.0185(7) 0.0182(7) 0.0046(6) 0.0060(6) 0.0005(6) C14 0.0270(8) 0.0198(7) 0.0177(7) 0.0083(6) 0.0048(6) 0.0009(6) C15 0.0261(8) 0.0203(7) 0.0185(7) 0.0071(6) 0.0070(6) 0.0028(6) C16 0.0211(7) 0.0190(7) 0.0167(7) 0.0061(5) 0.0042(5) 0.0018(6) C17 0.0239(7) 0.0209(7) 0.0164(7) 0.0050(6) 0.0058(6) 0.0018(6) C18 0.0192(7) 0.0210(7) 0.0166(7) 0.0057(5) 0.0035(5) 0.0011(6) C19 0.0211(7) 0.0230(7) 0.0163(7) 0.0057(6) 0.0042(6) 0.0011(6) C20 0.0249(8) 0.0246(8) 0.0218(7) 0.0110(6) 0.0066(6) 0.0034(6) C21 0.0297(9) 0.0387(10) 0.0244(8) 0.0177(7) 0.0086(7) 0.0081(7) N1 0.0202(6) 0.0266(7) 0.0228(7) 0.0121(5) 0.0062(5) 0.0033(5) O1 0.0354(7) 0.0197(5) 0.0168(5) 0.0065(4) 0.0080(5) -0.0012(5) C22 0.0252(8) 0.0200(7) 0.0192(7) 0.0089(6) 0.0043(6) 0.0028(6) C23 0.0263(7) 0.0150(6) 0.0154(6) 0.0058(5) 0.0042(6) 0.0016(6) C24 0.0257(8) 0.0169(7) 0.0145(6) 0.0063(5) 0.0031(6) 0.0013(6) F1 0.0406(6) 0.0222(5) 0.0368(6) 0.0147(4) 0.0194(5) 0.0126(4) F2 0.0270(5) 0.0428(6) 0.0249(5) 0.0163(5) -0.0024(4) -0.0034(5) F3 0.0260(5) 0.0328(5) 0.0141(4) 0.0089(4) 0.0010(4) -0.0008(4) F4 0.0430(6) 0.0161(4) 0.0281(5) 0.0098(4) 0.0165(4) 0.0083(4) F5 0.0394(6) 0.0238(5) 0.0343(6) 0.0188(4) 0.0161(5) 0.0130(4) F6 0.0297(5) 0.0417(6) 0.0140(4) 0.0062(4) -0.0001(4) -0.0091(5) I1 0.02261(6) 0.02132(6) 0.01920(6) 0.00956(4) 0.00659(4) 0.00218(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 C1 N1 1.335(2) . ? C1 C2 1.385(2) . ? C1 H1 0.9500 . ? C2 C3 1.398(2) . ? C2 H2 0.9500 . ? C3 C4 1.403(2) . ? C3 C6 1.460(2) . ? C4 C5 1.381(2) . ? C4 H4 0.9500 . ? C5 N1 1.342(2) . ? C5 H5 0.9500 . ? C6 C7 1.340(2) . ? C6 H6 0.9500 . ? C7 C8 1.463(2) . ? C7 H7 0.9500 . ? C8 C13 1.391(2) . ? C8 C9 1.402(2) . ? C9 C10 1.379(2) . ? C9 H9 0.9500 . ? C10 C11 1.395(2) . ? C10 H10 0.9500 . ? C11 O1 1.3606(18) . ? C11 C12 1.390(2) . ? C12 C13 1.389(2) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 O1 1.4329(19) . ? C14 C15 1.513(2) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.523(2) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.526(2) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.522(2) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.523(2) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C20 1.519(2) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 C21 1.522(2) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? N1 I1 2.7463(14) . ? C22 F2 1.3499(19) . ? C22 F1 1.3524(19) . ? C22 C23 1.539(2) . ? C22 I1 2.1640(15) . ? C23 F3 1.3440(18) . ? C23 F4 1.3454(17) . ? C23 C24 1.555(2) . ? C24 F5 1.3405(18) . ? C24 F6 1.3465(18) . ? C24 C24 1.558(3) 2_467 ? 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 N1 C1 C2 123.29(15) . . ? N1 C1 H1 118.4 . . ? C2 C1 H1 118.4 . . ? C1 C2 C3 119.94(15) . . ? C1 C2 H2 120.0 . . ? C3 C2 H2 120.0 . . ? C2 C3 C4 116.51(14) . . ? C2 C3 C6 118.86(14) . . ? C4 C3 C6 124.63(14) . . ? C5 C4 C3 119.52(15) . . ? C5 C4 H4 120.2 . . ? C3 C4 H4 120.2 . . ? N1 C5 C4 123.59(15) . . ? N1 C5 H5 118.2 . . ? C4 C5 H5 118.2 . . ? C7 C6 C3 127.76(15) . . ? C7 C6 H6 116.1 . . ? C3 C6 H6 116.1 . . ? C6 C7 C8 124.79(15) . . ? C6 C7 H7 117.6 . . ? C8 C7 H7 117.6 . . ? C13 C8 C9 117.41(14) . . ? C13 C8 C7 120.77(14) . . ? C9 C8 C7 121.81(14) . . ? C10 C9 C8 121.15(15) . . ? C10 C9 H9 119.4 . . ? C8 C9 H9 119.4 . . ? C9 C10 C11 120.42(15) . . ? C9 C10 H10 119.8 . . ? C11 C10 H10 119.8 . . ? O1 C11 C12 125.29(14) . . ? O1 C11 C10 115.17(14) . . ? C12 C11 C10 119.54(14) . . ? C13 C12 C11 119.24(15) . . ? C13 C12 H12 120.4 . . ? C11 C12 H12 120.4 . . ? C12 C13 C8 122.21(15) . . ? C12 C13 H13 118.9 . . ? C8 C13 H13 118.9 . . ? O1 C14 C15 105.86(12) . . ? O1 C14 H14A 110.6 . . ? C15 C14 H14A 110.6 . . ? O1 C14 H14B 110.6 . . ? C15 C14 H14B 110.6 . . ? H14A C14 H14B 108.7 . . ? C14 C15 C16 113.64(13) . . ? C14 C15 H15A 108.8 . . ? C16 C15 H15A 108.8 . . ? C14 C15 H15B 108.8 . . ? C16 C15 H15B 108.8 . . ? H15A C15 H15B 107.7 . . ? C15 C16 C17 111.14(13) . . ? C15 C16 H16A 109.4 . . ? C17 C16 H16A 109.4 . . ? C15 C16 H16B 109.4 . . ? C17 C16 H16B 109.4 . . ? H16A C16 H16B 108.0 . . ? C18 C17 C16 114.47(13) . . ? C18 C17 H17A 108.6 . . ? C16 C17 H17A 108.6 . . ? C18 C17 H17B 108.6 . . ? C16 C17 H17B 108.6 . . ? H17A C17 H17B 107.6 . . ? C17 C18 C19 112.41(13) . . ? C17 C18 H18A 109.1 . . ? C19 C18 H18A 109.1 . . ? C17 C18 H18B 109.1 . . ? C19 C18 H18B 109.1 . . ? H18A C18 H18B 107.9 . . ? C20 C19 C18 114.13(13) . . ? C20 C19 H19A 108.7 . . ? C18 C19 H19A 108.7 . . ? C20 C19 H19B 108.7 . . ? C18 C19 H19B 108.7 . . ? H19A C19 H19B 107.6 . . ? C19 C20 C21 112.48(14) . . ? C19 C20 H20A 109.1 . . ? C21 C20 H20A 109.1 . . ? C19 C20 H20B 109.1 . . ? C21 C20 H20B 109.1 . . ? H20A C20 H20B 107.8 . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C1 N1 C5 117.15(14) . . ? C1 N1 I1 114.79(10) . . ? C5 N1 I1 127.77(11) . . ? C11 O1 C14 118.62(12) . . ? F2 C22 F1 107.00(13) . . ? F2 C22 C23 108.72(13) . . ? F1 C22 C23 108.62(13) . . ? F2 C22 I1 109.90(10) . . ? F1 C22 I1 109.83(10) . . ? C23 C22 I1 112.61(10) . . ? F3 C23 F4 108.57(13) . . ? F3 C23 C22 107.71(12) . . ? F4 C23 C22 108.32(13) . . ? F3 C23 C24 109.06(12) . . ? F4 C23 C24 107.03(12) . . ? C22 C23 C24 115.96(13) . . ? F5 C24 F6 108.53(13) . . ? F5 C24 C23 109.45(12) . . ? F6 C24 C23 107.30(12) . . ? F5 C24 C24 108.24(15) . 2_467 ? F6 C24 C24 108.45(15) . 2_467 ? C23 C24 C24 114.72(16) . 2_467 ? C22 I1 N1 177.00(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 N1 C1 C2 C3 -0.1(3) . . . . ? C1 C2 C3 C4 0.6(2) . . . . ? C1 C2 C3 C6 179.84(15) . . . . ? C2 C3 C4 C5 -0.6(2) . . . . ? C6 C3 C4 C5 -179.82(15) . . . . ? C3 C4 C5 N1 0.2(2) . . . . ? C2 C3 C6 C7 179.60(16) . . . . ? C4 C3 C6 C7 -1.2(3) . . . . ? C3 C6 C7 C8 177.84(15) . . . . ? C6 C7 C8 C13 166.99(17) . . . . ? C6 C7 C8 C9 -13.9(3) . . . . ? C13 C8 C9 C10 -1.5(3) . . . . ? C7 C8 C9 C10 179.43(16) . . . . ? C8 C9 C10 C11 0.5(3) . . . . ? C9 C10 C11 O1 -179.47(16) . . . . ? C9 C10 C11 C12 0.8(3) . . . . ? O1 C11 C12 C13 179.32(16) . . . . ? C10 C11 C12 C13 -1.0(3) . . . . ? C11 C12 C13 C8 -0.1(3) . . . . ? C9 C8 C13 C12 1.3(3) . . . . ? C7 C8 C13 C12 -179.60(16) . . . . ? O1 C14 C15 C16 -178.29(13) . . . . ? C14 C15 C16 C17 -176.59(14) . . . . ? C15 C16 C17 C18 -177.06(13) . . . . ? C16 C17 C18 C19 -177.60(13) . . . . ? C17 C18 C19 C20 -176.98(14) . . . . ? C18 C19 C20 C21 174.29(14) . . . . ? C2 C1 N1 C5 -0.4(2) . . . . ? C2 C1 N1 I1 -174.62(13) . . . . ? C4 C5 N1 C1 0.3(2) . . . . ? C4 C5 N1 I1 173.74(12) . . . . ? C12 C11 O1 C14 5.4(2) . . . . ? C10 C11 O1 C14 -174.31(15) . . . . ? C15 C14 O1 C11 177.72(14) . . . . ? F2 C22 C23 F3 -175.20(12) . . . . ? F1 C22 C23 F3 -59.10(15) . . . . ? I1 C22 C23 F3 62.77(13) . . . . ? F2 C22 C23 F4 67.55(15) . . . . ? F1 C22 C23 F4 -176.35(12) . . . . ? I1 C22 C23 F4 -54.48(14) . . . . ? F2 C22 C23 C24 -52.74(17) . . . . ? F1 C22 C23 C24 63.36(17) . . . . ? I1 C22 C23 C24 -174.77(10) . . . . ? F3 C23 C24 F5 72.02(16) . . . . ? F4 C23 C24 F5 -170.71(13) . . . . ? C22 C23 C24 F5 -49.73(17) . . . . ? F3 C23 C24 F6 -170.40(12) . . . . ? F4 C23 C24 F6 -53.13(16) . . . . ? C22 C23 C24 F6 67.85(16) . . . . ? F3 C23 C24 C24 -49.9(2) . . . 2_467 ? F4 C23 C24 C24 67.42(19) . . . 2_467 ? C22 C23 C24 C24 -171.60(15) . . . 2_467 ? _diffrn_measured_fraction_theta_max 0.964 _diffrn_reflns_theta_full 30.01 _diffrn_measured_fraction_theta_full 0.964 _refine_diff_density_max 1.172 _refine_diff_density_min -0.521 _refine_diff_density_rms 0.082