# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # 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_mg177s _audit_creation_date 2012-08-22 _audit_creation_method ; Olex2 1.1 (compiled Nov 1 2011 20:42:30, GUI svn.r3906) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C28 H40 N8 O2, 3(C6 F5 I)' _chemical_formula_sum 'C46 H40 F15 I3 N8 O2' _chemical_formula_weight 1402.56 _chemical_melting_point ? 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' _cell_length_a 12.787(3) _cell_length_b 13.339(3) _cell_length_c 16.139(4) _cell_angle_alpha 65.969(4) _cell_angle_beta 83.547(4) _cell_angle_gamma 85.330(4) _cell_volume 2496.4(11) _cell_formula_units_Z 2 _cell_measurement_reflns_used 6627 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 26.368 _cell_measurement_theta_min 2.198 _exptl_absorpt_coefficient_mu 1.982 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_correction_T_min 0.772607 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS Version 2.05 (Bruker, 2001)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.866 _exptl_crystal_density_meas . _exptl_crystal_density_method 'not measured' _exptl_crystal_description irregular _exptl_crystal_F_000 1364 _exptl_crystal_recrystallization_method 'Slow evaporation from CH2Cl2' _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.2 _exptl_special_details ; The data collection nominally covered a full sphere of reciprocal space by a combination of 6 sets of \w and \f scans each set at different \f and/or \w angles and each scan (15 s exposure) covering -0.300\% degrees. The crystal to detector distance was 4.954 cm. ; _diffrn_reflns_av_R_equivalents 0.0362 _diffrn_reflns_av_unetI/netI 0.0324 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 41108 _diffrn_reflns_theta_full 26.51 _diffrn_reflns_theta_max 26.51 _diffrn_reflns_theta_min 1.60 _diffrn_ambient_temperature 100(2) _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.988 _diffrn_measured_fraction_theta_max 0.988 _diffrn_measurement_device_type 'Bruker SMART APEX CCD diffractometer' _diffrn_measurement_method 'omega and phi scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'sealed tube' _diffrn_source_current 37.0 _diffrn_source_power 1.739 _diffrn_source_target Mo _diffrn_source_voltage 47.0 _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 8984 _reflns_number_total 10236 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'SAINT-Plus Version 6.45 (Bruker, 2001)' _computing_data_collection 'SMART Version 5.625 (Bruker, 2001)' _computing_data_reduction 'SAINT-Plus Version 6.45 (Bruker, 2001)' _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _refine_diff_density_max 1.158 _refine_diff_density_min -0.343 _refine_diff_density_rms 0.101 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 673 _refine_ls_number_reflns 10236 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0357 _refine_ls_R_factor_gt 0.0293 _refine_ls_restrained_S_all 1.046 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0395P)^2^+0.2126P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0682 _refine_ls_wR_factor_ref 0.0713 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 O1 O 0.34470(15) 0.74821(16) 0.13991(13) 0.0231(4) Uani 1 1 d . . . O2 O 0.63990(15) 0.94094(16) 0.20768(13) 0.0228(4) Uani 1 1 d . . . N1 N 0.38497(18) 0.59844(19) 0.26552(16) 0.0207(5) Uani 1 1 d . . . N2 N 0.48340(19) 0.44652(19) 0.24724(16) 0.0222(5) Uani 1 1 d . . . N3 N 0.47146(18) 0.62604(19) 0.12405(16) 0.0208(5) Uani 1 1 d . . . N4 N 0.43366(18) 0.74230(19) 0.35227(16) 0.0206(5) Uani 1 1 d . . . N5 N 0.65390(17) 0.78956(19) 0.33953(16) 0.0193(5) Uani 1 1 d . . . N6 N 0.79289(18) 0.65277(19) 0.34837(16) 0.0210(5) Uani 1 1 d . . . N7 N 0.74512(17) 0.79629(19) 0.20454(15) 0.0198(5) Uani 1 1 d . . . N8 N 0.63032(18) 0.78266(19) 0.06291(15) 0.0197(5) Uani 1 1 d . . . C1 C 0.3984(2) 0.6622(2) 0.17477(19) 0.0195(6) Uani 1 1 d . . . C2 C 0.4573(2) 0.5033(2) 0.3059(2) 0.0275(7) Uani 1 1 d . . . H2A H 0.5226 0.5284 0.3177 0.033 Uiso 1 1 calc R . . H2B H 0.4241 0.4521 0.3649 0.033 Uiso 1 1 calc R . . C3 C 0.5350(2) 0.5232(2) 0.1636(2) 0.0271(7) Uani 1 1 d . . . H3A H 0.5477 0.4890 0.1191 0.033 Uiso 1 1 calc R . . H3B H 0.6041 0.5402 0.1759 0.033 Uiso 1 1 calc R . . C4 C 0.3096(2) 0.6361(2) 0.3217(2) 0.0257(7) Uani 1 1 d . . . H4A H 0.3036 0.5779 0.3842 0.031 Uiso 1 1 calc R . . H4B H 0.2398 0.6471 0.2976 0.031 Uiso 1 1 calc R . . C5 C 0.3373(2) 0.7417(2) 0.32657(18) 0.0194(6) Uani 1 1 d . . . C6 C 0.2670(2) 0.8309(3) 0.3055(2) 0.0253(7) Uani 1 1 d . . . H6 H 0.1991 0.8269 0.2886 0.030 Uiso 1 1 calc R . . C7 C 0.2966(2) 0.9262(2) 0.30934(19) 0.0243(6) Uani 1 1 d . . . H7 H 0.2493 0.9883 0.2960 0.029 Uiso 1 1 calc R . . C8 C 0.3969(2) 0.9294(2) 0.33309(19) 0.0225(6) Uani 1 1 d . . . H8 H 0.4203 0.9946 0.3343 0.027 Uiso 1 1 calc R . . C9 C 0.4620(2) 0.8360(2) 0.35501(19) 0.0199(6) Uani 1 1 d . . . C10 C 0.5703(2) 0.8348(2) 0.3849(2) 0.0237(6) Uani 1 1 d . . . H10A H 0.5870 0.9109 0.3729 0.028 Uiso 1 1 calc R . . H10B H 0.5689 0.7912 0.4514 0.028 Uiso 1 1 calc R . . C11 C 0.6771(2) 0.8462(2) 0.24811(19) 0.0186(6) Uani 1 1 d . . . C12 C 0.6874(2) 0.6738(2) 0.3828(2) 0.0219(6) Uani 1 1 d . . . H12A H 0.6854 0.6518 0.4494 0.026 Uiso 1 1 calc R . . H12B H 0.6376 0.6285 0.3717 0.026 Uiso 1 1 calc R . . C13 C 0.7907(2) 0.6848(2) 0.2514(2) 0.0236(6) Uani 1 1 d . . . H13A H 0.7490 0.6319 0.2414 0.028 Uiso 1 1 calc R . . H13B H 0.8634 0.6809 0.2242 0.028 Uiso 1 1 calc R . . C14 C 0.7729(2) 0.8561(3) 0.10724(19) 0.0247(7) Uani 1 1 d . . . H14A H 0.8332 0.8164 0.0883 0.030 Uiso 1 1 calc R . . H14B H 0.7967 0.9294 0.0970 0.030 Uiso 1 1 calc R . . C15 C 0.6856(2) 0.8717(2) 0.04666(19) 0.0194(6) Uani 1 1 d . . . C16 C 0.6668(2) 0.9727(2) -0.02359(19) 0.0228(6) Uani 1 1 d . . . H16 H 0.7073 1.0336 -0.0330 0.027 Uiso 1 1 calc R . . C17 C 0.5890(2) 0.9843(2) -0.07962(19) 0.0253(7) Uani 1 1 d . . . H17 H 0.5753 1.0528 -0.1282 0.030 Uiso 1 1 calc R . . C18 C 0.5311(2) 0.8940(2) -0.06381(19) 0.0226(6) Uani 1 1 d . . . H18 H 0.4772 0.8990 -0.1015 0.027 Uiso 1 1 calc R . . C19 C 0.5538(2) 0.7954(2) 0.00863(18) 0.0183(6) Uani 1 1 d . . . C20 C 0.4922(2) 0.6950(2) 0.0280(2) 0.0245(6) Uani 1 1 d . . . H20A H 0.4242 0.7192 0.0007 0.029 Uiso 1 1 calc R . . H20B H 0.5318 0.6505 -0.0023 0.029 Uiso 1 1 calc R . . C21 C 0.4036(2) 0.3769(2) 0.2371(2) 0.0241(6) Uani 1 1 d . . . C22 C 0.3282(3) 0.4385(3) 0.1635(2) 0.0367(8) Uani 1 1 d . . . H22A H 0.2863 0.4942 0.1791 0.055 Uiso 1 1 calc R . . H22B H 0.2812 0.3864 0.1595 0.055 Uiso 1 1 calc R . . H22C H 0.3689 0.4742 0.1046 0.055 Uiso 1 1 calc R . . C23 C 0.3394(3) 0.3206(3) 0.3279(2) 0.0365(8) Uani 1 1 d . . . H23A H 0.3869 0.2880 0.3766 0.055 Uiso 1 1 calc R . . H23B H 0.2989 0.2628 0.3253 0.055 Uiso 1 1 calc R . . H23C H 0.2910 0.3747 0.3403 0.055 Uiso 1 1 calc R . . C24 C 0.4661(3) 0.2863(3) 0.2146(2) 0.0333(8) Uani 1 1 d . . . H24A H 0.5139 0.3200 0.1597 0.050 Uiso 1 1 calc R . . H24B H 0.4171 0.2407 0.2042 0.050 Uiso 1 1 calc R . . H24C H 0.5070 0.2406 0.2656 0.050 Uiso 1 1 calc R . . C25 C 0.8851(2) 0.6908(2) 0.3781(2) 0.0224(6) Uani 1 1 d . . . C26 C 0.9048(2) 0.8140(3) 0.3289(2) 0.0320(8) Uani 1 1 d . . . H26A H 0.9167 0.8337 0.2632 0.048 Uiso 1 1 calc R . . H26B H 0.9670 0.8307 0.3507 0.048 Uiso 1 1 calc R . . H26C H 0.8433 0.8561 0.3414 0.048 Uiso 1 1 calc R . . C27 C 0.9839(2) 0.6260(3) 0.3610(3) 0.0354(8) Uani 1 1 d . . . H27A H 0.9732 0.5472 0.3940 0.053 Uiso 1 1 calc R . . H27B H 1.0446 0.6460 0.3824 0.053 Uiso 1 1 calc R . . H27C H 0.9970 0.6437 0.2956 0.053 Uiso 1 1 calc R . . C28 C 0.8668(3) 0.6616(3) 0.4801(2) 0.0335(8) Uani 1 1 d . . . H28A H 0.8114 0.7108 0.4915 0.050 Uiso 1 1 calc R . . H28B H 0.9321 0.6697 0.5029 0.050 Uiso 1 1 calc R . . H28C H 0.8452 0.5854 0.5115 0.050 Uiso 1 1 calc R . . I31 I 0.164179(14) 0.758566(15) 0.061857(13) 0.02171(6) Uani 1 1 d . . . F31 F 0.02280(13) 0.58542(14) 0.03776(12) 0.0312(4) Uani 1 1 d . . . F32 F -0.14705(15) 0.61080(15) -0.05467(14) 0.0391(5) Uani 1 1 d . . . F33 F -0.22298(14) 0.81446(15) -0.15749(13) 0.0371(5) Uani 1 1 d . . . F34 F -0.12598(13) 0.99467(14) -0.16803(12) 0.0307(4) Uani 1 1 d . . . F35 F 0.03858(12) 0.97124(13) -0.07230(11) 0.0248(4) Uani 1 1 d . . . C31 C 0.0338(2) 0.7776(2) -0.01179(19) 0.0196(6) Uani 1 1 d . . . C32 C -0.0148(2) 0.6877(2) -0.0099(2) 0.0234(6) Uani 1 1 d . . . C33 C -0.1017(2) 0.6988(3) -0.0571(2) 0.0271(7) Uani 1 1 d . . . C34 C -0.1400(2) 0.8023(3) -0.1100(2) 0.0258(7) Uani 1 1 d . . . C35 C -0.0910(2) 0.8936(2) -0.1148(2) 0.0231(6) Uani 1 1 d . . . C36 C -0.0057(2) 0.8800(2) -0.06567(19) 0.0198(6) Uani 1 1 d . . . I41 I 0.749347(14) 1.105235(15) 0.215324(13) 0.02214(6) Uani 1 1 d . . . F41 F 0.72261(14) 1.36800(15) 0.13578(14) 0.0397(5) Uani 1 1 d . . . F42 F 0.83439(16) 1.52238(16) 0.14795(16) 0.0468(6) Uani 1 1 d . . . F43 F 1.01460(18) 1.46503(18) 0.23480(15) 0.0529(6) Uani 1 1 d . . . F44 F 1.08001(17) 1.25091(19) 0.31076(15) 0.0548(6) Uani 1 1 d . . . F45 F 0.96560(15) 1.09442(16) 0.30402(13) 0.0390(5) Uani 1 1 d . . . C41 C 0.8399(2) 1.2265(2) 0.2201(2) 0.0252(7) Uani 1 1 d . . . C42 C 0.8104(2) 1.3360(3) 0.1806(2) 0.0288(7) Uani 1 1 d . . . C43 C 0.8686(3) 1.4164(3) 0.1854(2) 0.0351(8) Uani 1 1 d . . . C44 C 0.9586(3) 1.3878(3) 0.2288(2) 0.0379(9) Uani 1 1 d . . . C45 C 0.9910(3) 1.2795(3) 0.2682(2) 0.0364(8) Uani 1 1 d . . . C46 C 0.9316(3) 1.2001(3) 0.2641(2) 0.0302(7) Uani 1 1 d . . . I51 I 0.783726(15) 0.407514(15) 0.419880(13) 0.02345(6) Uani 1 1 d . . . F51 F 0.58725(14) 0.28625(15) 0.40520(13) 0.0351(4) Uani 1 1 d . . . F52 F 0.55830(14) 0.07909(15) 0.42982(13) 0.0374(5) Uani 1 1 d . . . F53 F 0.71301(16) -0.07814(14) 0.49352(13) 0.0367(5) Uani 1 1 d . . . F54 F 0.89617(15) -0.02519(16) 0.53115(16) 0.0471(5) Uani 1 1 d . . . F55 F 0.93010(14) 0.18472(15) 0.50040(15) 0.0419(5) Uani 1 1 d . . . C51 C 0.7605(2) 0.2422(2) 0.44947(19) 0.0213(6) Uani 1 1 d . . . C52 C 0.6658(2) 0.2122(2) 0.43403(19) 0.0224(6) Uani 1 1 d . . . C53 C 0.6505(2) 0.1054(2) 0.4467(2) 0.0239(6) Uani 1 1 d . . . C54 C 0.7287(2) 0.0265(2) 0.4785(2) 0.0261(7) Uani 1 1 d . . . C55 C 0.8222(2) 0.0532(3) 0.4971(2) 0.0278(7) Uani 1 1 d . . . C56 C 0.8370(2) 0.1610(3) 0.4823(2) 0.0255(7) 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 O1 0.0233(10) 0.0203(11) 0.0265(11) -0.0085(9) -0.0110(9) 0.0013(8) O2 0.0247(10) 0.0178(11) 0.0259(11) -0.0071(9) -0.0087(9) -0.0010(8) N1 0.0235(12) 0.0181(13) 0.0213(13) -0.0081(10) -0.0047(10) 0.0005(10) N2 0.0254(13) 0.0186(13) 0.0239(13) -0.0086(11) -0.0063(10) -0.0021(10) N3 0.0225(12) 0.0172(13) 0.0226(13) -0.0076(10) -0.0017(10) -0.0032(10) N4 0.0213(12) 0.0204(13) 0.0212(12) -0.0101(10) -0.0012(10) 0.0011(10) N5 0.0188(11) 0.0196(13) 0.0206(12) -0.0089(10) -0.0038(9) 0.0004(9) N6 0.0186(12) 0.0188(13) 0.0274(13) -0.0106(11) -0.0036(10) -0.0015(10) N7 0.0183(11) 0.0222(13) 0.0199(12) -0.0086(10) -0.0038(9) -0.0022(10) N8 0.0201(12) 0.0188(13) 0.0193(12) -0.0065(10) -0.0018(10) -0.0025(9) C1 0.0178(13) 0.0185(15) 0.0253(15) -0.0095(12) -0.0075(11) -0.0060(11) C2 0.0355(17) 0.0232(16) 0.0270(17) -0.0108(14) -0.0141(14) 0.0006(13) C3 0.0211(15) 0.0253(17) 0.0350(18) -0.0120(14) -0.0027(13) -0.0019(12) C4 0.0252(15) 0.0278(17) 0.0246(16) -0.0108(14) 0.0011(12) -0.0077(13) C5 0.0218(14) 0.0208(15) 0.0155(14) -0.0073(12) 0.0000(11) -0.0022(11) C6 0.0217(15) 0.0307(18) 0.0230(16) -0.0092(14) -0.0046(12) -0.0022(13) C7 0.0272(15) 0.0230(16) 0.0225(15) -0.0098(13) -0.0045(12) 0.0065(12) C8 0.0298(16) 0.0193(15) 0.0190(15) -0.0085(12) 0.0001(12) -0.0032(12) C9 0.0202(14) 0.0233(16) 0.0185(14) -0.0112(12) -0.0002(11) -0.0005(12) C10 0.0255(15) 0.0249(16) 0.0241(16) -0.0130(13) -0.0047(12) 0.0002(12) C11 0.0166(13) 0.0195(15) 0.0232(15) -0.0101(12) -0.0066(11) -0.0049(11) C12 0.0192(14) 0.0193(15) 0.0245(15) -0.0052(12) -0.0040(12) -0.0028(11) C13 0.0270(15) 0.0195(15) 0.0287(16) -0.0131(13) -0.0059(13) -0.0011(12) C14 0.0221(14) 0.0311(17) 0.0208(15) -0.0095(13) 0.0003(12) -0.0083(13) C15 0.0178(13) 0.0233(16) 0.0184(14) -0.0097(12) 0.0004(11) -0.0033(11) C16 0.0280(15) 0.0203(16) 0.0212(15) -0.0100(13) 0.0045(12) -0.0071(12) C17 0.0347(17) 0.0178(15) 0.0171(15) -0.0025(12) 0.0015(12) 0.0038(13) C18 0.0232(15) 0.0285(17) 0.0162(14) -0.0092(13) -0.0040(11) 0.0028(12) C19 0.0208(14) 0.0183(15) 0.0155(14) -0.0072(12) 0.0011(11) -0.0014(11) C20 0.0269(15) 0.0254(17) 0.0235(16) -0.0104(13) -0.0066(12) -0.0040(13) C21 0.0288(15) 0.0213(16) 0.0240(16) -0.0089(13) -0.0084(12) -0.0038(12) C22 0.0397(19) 0.0287(18) 0.046(2) -0.0131(16) -0.0223(16) -0.0081(15) C23 0.0317(17) 0.036(2) 0.0369(19) -0.0070(16) -0.0049(15) -0.0110(15) C24 0.0427(19) 0.0268(18) 0.0360(19) -0.0166(15) -0.0106(15) -0.0009(15) C25 0.0190(14) 0.0183(15) 0.0298(16) -0.0083(13) -0.0071(12) -0.0012(11) C26 0.0279(16) 0.0260(18) 0.042(2) -0.0092(15) -0.0159(14) -0.0058(13) C27 0.0217(16) 0.035(2) 0.052(2) -0.0203(17) -0.0049(15) -0.0013(14) C28 0.0340(18) 0.039(2) 0.0293(18) -0.0122(15) -0.0088(14) -0.0096(15) I31 0.01950(10) 0.02229(11) 0.02334(11) -0.00773(8) -0.00669(7) -0.00191(7) F31 0.0314(10) 0.0182(9) 0.0418(11) -0.0072(8) -0.0149(8) 0.0011(7) F32 0.0375(10) 0.0253(10) 0.0619(13) -0.0198(10) -0.0235(10) -0.0039(8) F33 0.0318(10) 0.0329(11) 0.0513(12) -0.0167(9) -0.0264(9) 0.0027(8) F34 0.0285(9) 0.0235(10) 0.0377(10) -0.0083(8) -0.0137(8) 0.0046(7) F35 0.0230(8) 0.0202(9) 0.0338(10) -0.0130(8) -0.0034(7) -0.0030(7) C31 0.0160(13) 0.0226(15) 0.0218(15) -0.0104(12) -0.0020(11) -0.0012(11) C32 0.0236(15) 0.0193(16) 0.0258(16) -0.0068(13) -0.0063(12) 0.0004(12) C33 0.0234(15) 0.0245(17) 0.0385(18) -0.0162(15) -0.0080(13) -0.0030(12) C34 0.0209(14) 0.0268(17) 0.0334(17) -0.0144(14) -0.0114(13) 0.0036(12) C35 0.0214(14) 0.0206(16) 0.0261(16) -0.0084(13) -0.0054(12) 0.0046(12) C36 0.0161(13) 0.0214(15) 0.0252(15) -0.0131(13) 0.0007(11) -0.0027(11) I41 0.02580(10) 0.01873(10) 0.02289(11) -0.00961(8) -0.00048(8) -0.00192(7) F41 0.0303(10) 0.0239(10) 0.0637(14) -0.0173(10) -0.0038(9) 0.0030(8) F42 0.0468(12) 0.0252(11) 0.0724(15) -0.0278(11) 0.0137(11) -0.0051(9) F43 0.0640(14) 0.0545(14) 0.0545(14) -0.0348(12) 0.0105(11) -0.0341(12) F44 0.0511(13) 0.0654(16) 0.0468(13) -0.0147(12) -0.0166(11) -0.0227(12) F45 0.0411(11) 0.0337(11) 0.0357(11) -0.0046(9) -0.0122(9) -0.0037(9) C41 0.0270(15) 0.0255(17) 0.0276(16) -0.0161(14) 0.0051(13) -0.0072(13) C42 0.0261(16) 0.0264(18) 0.0370(19) -0.0178(15) 0.0059(14) -0.0030(13) C43 0.042(2) 0.0242(18) 0.043(2) -0.0206(16) 0.0160(16) -0.0071(15) C44 0.043(2) 0.043(2) 0.039(2) -0.0285(18) 0.0115(16) -0.0199(17) C45 0.0381(19) 0.045(2) 0.0271(18) -0.0143(16) -0.0009(15) -0.0130(16) C46 0.0361(18) 0.0285(18) 0.0256(17) -0.0105(14) -0.0004(14) -0.0053(14) I51 0.02956(11) 0.01803(11) 0.02377(11) -0.00913(8) -0.00123(8) -0.00416(8) F51 0.0318(10) 0.0248(10) 0.0438(11) -0.0059(9) -0.0170(9) 0.0019(8) F52 0.0376(11) 0.0317(11) 0.0420(11) -0.0095(9) -0.0139(9) -0.0121(8) F53 0.0510(12) 0.0192(10) 0.0428(11) -0.0137(9) -0.0075(9) -0.0068(8) F54 0.0388(11) 0.0260(11) 0.0756(16) -0.0184(11) -0.0193(11) 0.0123(9) F55 0.0281(10) 0.0319(11) 0.0709(15) -0.0224(11) -0.0186(10) -0.0001(8) C51 0.0282(15) 0.0196(15) 0.0181(14) -0.0089(12) -0.0023(12) -0.0039(12) C52 0.0259(15) 0.0188(15) 0.0176(14) -0.0022(12) -0.0043(12) 0.0017(12) C53 0.0306(16) 0.0250(16) 0.0188(15) -0.0099(13) -0.0029(12) -0.0083(13) C54 0.0382(17) 0.0193(16) 0.0231(16) -0.0106(13) -0.0012(13) -0.0048(13) C55 0.0297(16) 0.0218(16) 0.0318(17) -0.0108(14) -0.0077(13) 0.0064(13) C56 0.0232(15) 0.0283(17) 0.0284(16) -0.0140(14) -0.0054(12) -0.0015(13) _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 O1 C1 1.240(3) . ? O1 I31 2.719(2) . ? O2 C11 1.245(3) . ? O2 I41 2.745(2) . ? N1 C1 1.360(4) . ? N1 C2 1.470(4) . ? N1 C4 1.449(4) . ? N2 C2 1.433(4) . ? N2 C3 1.445(4) . ? N2 C21 1.498(4) . ? N3 C1 1.360(4) . ? N3 C3 1.473(4) . ? N3 C20 1.451(4) . ? N4 C5 1.346(4) . ? N4 C9 1.349(4) . ? N5 C10 1.456(3) . ? N5 C11 1.366(4) . ? N5 C12 1.461(4) . ? N6 C12 1.450(3) . ? N6 C13 1.448(4) . ? N6 C25 1.517(3) . ? N6 I51 3.001(2) . ? N7 C11 1.358(4) . ? N7 C13 1.471(4) . ? N7 C14 1.459(4) . ? N8 C15 1.350(3) . ? N8 C19 1.341(4) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C4 C5 1.514(4) . ? C5 C6 1.380(4) . ? C6 H6 0.9500 . ? C6 C7 1.383(4) . ? C7 H7 0.9500 . ? C7 C8 1.387(4) . ? C8 H8 0.9500 . ? C8 C9 1.381(4) . ? C9 C10 1.513(4) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C14 C15 1.512(4) . ? C15 C16 1.387(4) . ? C16 H16 0.9500 . ? C16 C17 1.377(4) . ? C17 H17 0.9500 . ? C17 C18 1.384(4) . ? C18 H18 0.9500 . ? C18 C19 1.393(4) . ? C19 C20 1.512(4) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 C22 1.534(4) . ? C21 C23 1.523(4) . ? C21 C24 1.538(4) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 C26 1.534(4) . ? C25 C27 1.535(4) . ? C25 C28 1.524(4) . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? I31 C31 2.094(3) . ? F31 C32 1.344(3) . ? F32 C33 1.335(3) . ? F33 C34 1.339(3) . ? F34 C35 1.342(3) . ? F35 C36 1.344(3) . ? C31 C32 1.383(4) . ? C31 C36 1.377(4) . ? C32 C33 1.381(4) . ? C33 C34 1.378(4) . ? C34 C35 1.384(4) . ? C35 C36 1.377(4) . ? I41 C41 2.095(3) . ? F41 C42 1.348(4) . ? F42 C43 1.348(4) . ? F43 C44 1.342(4) . ? F44 C45 1.344(4) . ? F45 C46 1.347(4) . ? C41 C42 1.374(4) . ? C41 C46 1.385(4) . ? C42 C43 1.387(4) . ? C43 C44 1.361(5) . ? C44 C45 1.369(5) . ? C45 C46 1.380(5) . ? I51 C51 2.097(3) . ? F51 C52 1.330(3) . ? F52 C53 1.343(3) . ? F53 C54 1.344(3) . ? F54 C55 1.334(3) . ? F55 C56 1.349(3) . ? C51 C52 1.385(4) . ? C51 C56 1.374(4) . ? C52 C53 1.381(4) . ? C53 C54 1.370(4) . ? C54 C55 1.372(4) . ? C55 C56 1.384(4) . ? 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 C1 O1 I31 123.33(16) . . ? C11 O2 I41 115.23(16) . . ? C1 N1 C2 119.5(2) . . ? C1 N1 C4 118.4(2) . . ? C4 N1 C2 121.5(2) . . ? C2 N2 C3 107.2(2) . . ? C2 N2 C21 119.7(2) . . ? C3 N2 C21 116.1(2) . . ? C1 N3 C3 122.8(2) . . ? C1 N3 C20 118.6(2) . . ? C20 N3 C3 118.6(2) . . ? C5 N4 C9 117.4(2) . . ? C10 N5 C12 119.9(2) . . ? C11 N5 C10 117.8(2) . . ? C11 N5 C12 119.6(2) . . ? C12 N6 C25 118.2(2) . . ? C12 N6 I51 97.31(15) . . ? C13 N6 C12 106.7(2) . . ? C13 N6 C25 116.4(2) . . ? C13 N6 I51 101.88(16) . . ? C25 N6 I51 113.52(16) . . ? C11 N7 C13 122.6(2) . . ? C11 N7 C14 118.2(2) . . ? C14 N7 C13 119.2(2) . . ? C19 N8 C15 117.2(2) . . ? O1 C1 N1 121.2(3) . . ? O1 C1 N3 121.8(3) . . ? N3 C1 N1 117.1(2) . . ? N1 C2 H2A 109.3 . . ? N1 C2 H2B 109.3 . . ? N2 C2 N1 111.6(2) . . ? N2 C2 H2A 109.3 . . ? N2 C2 H2B 109.3 . . ? H2A C2 H2B 108.0 . . ? N2 C3 N3 111.8(2) . . ? N2 C3 H3A 109.2 . . ? N2 C3 H3B 109.2 . . ? N3 C3 H3A 109.2 . . ? N3 C3 H3B 109.2 . . ? H3A C3 H3B 107.9 . . ? N1 C4 H4A 108.7 . . ? N1 C4 H4B 108.7 . . ? N1 C4 C5 114.4(2) . . ? H4A C4 H4B 107.6 . . ? C5 C4 H4A 108.7 . . ? C5 C4 H4B 108.7 . . ? N4 C5 C4 115.8(2) . . ? N4 C5 C6 122.9(3) . . ? C6 C5 C4 121.3(3) . . ? C5 C6 H6 120.5 . . ? C5 C6 C7 119.1(3) . . ? C7 C6 H6 120.5 . . ? C6 C7 H7 120.6 . . ? C6 C7 C8 118.8(3) . . ? C8 C7 H7 120.6 . . ? C7 C8 H8 120.6 . . ? C9 C8 C7 118.7(3) . . ? C9 C8 H8 120.6 . . ? N4 C9 C8 123.0(3) . . ? N4 C9 C10 116.6(2) . . ? C8 C9 C10 120.4(3) . . ? N5 C10 C9 114.1(2) . . ? N5 C10 H10A 108.7 . . ? N5 C10 H10B 108.7 . . ? C9 C10 H10A 108.7 . . ? C9 C10 H10B 108.7 . . ? H10A C10 H10B 107.6 . . ? O2 C11 N5 120.9(3) . . ? O2 C11 N7 121.9(3) . . ? N7 C11 N5 117.2(2) . . ? N5 C12 H12A 109.2 . . ? N5 C12 H12B 109.2 . . ? N6 C12 N5 112.0(2) . . ? N6 C12 H12A 109.2 . . ? N6 C12 H12B 109.2 . . ? H12A C12 H12B 107.9 . . ? N6 C13 N7 113.1(2) . . ? N6 C13 H13A 109.0 . . ? N6 C13 H13B 109.0 . . ? N7 C13 H13A 109.0 . . ? N7 C13 H13B 109.0 . . ? H13A C13 H13B 107.8 . . ? N7 C14 H14A 108.4 . . ? N7 C14 H14B 108.4 . . ? N7 C14 C15 115.4(2) . . ? H14A C14 H14B 107.5 . . ? C15 C14 H14A 108.4 . . ? C15 C14 H14B 108.4 . . ? N8 C15 C14 116.8(3) . . ? N8 C15 C16 122.5(3) . . ? C16 C15 C14 120.6(3) . . ? C15 C16 H16 120.2 . . ? C17 C16 C15 119.7(3) . . ? C17 C16 H16 120.2 . . ? C16 C17 H17 120.7 . . ? C16 C17 C18 118.7(3) . . ? C18 C17 H17 120.7 . . ? C17 C18 H18 120.8 . . ? C17 C18 C19 118.4(3) . . ? C19 C18 H18 120.8 . . ? N8 C19 C18 123.5(3) . . ? N8 C19 C20 116.5(2) . . ? C18 C19 C20 119.9(3) . . ? N3 C20 C19 114.4(2) . . ? N3 C20 H20A 108.7 . . ? N3 C20 H20B 108.7 . . ? C19 C20 H20A 108.7 . . ? C19 C20 H20B 108.7 . . ? H20A C20 H20B 107.6 . . ? N2 C21 C22 114.9(2) . . ? N2 C21 C23 109.6(2) . . ? N2 C21 C24 106.4(2) . . ? C22 C21 C24 109.4(3) . . ? C23 C21 C22 108.9(3) . . ? C23 C21 C24 107.2(3) . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22B 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C21 C23 H23A 109.5 . . ? C21 C23 H23B 109.5 . . ? C21 C23 H23C 109.5 . . ? H23A C23 H23B 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C21 C24 H24A 109.5 . . ? C21 C24 H24B 109.5 . . ? C21 C24 H24C 109.5 . . ? H24A C24 H24B 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? N6 C25 C26 115.0(2) . . ? N6 C25 C27 107.4(2) . . ? N6 C25 C28 108.6(2) . . ? C26 C25 C27 108.7(2) . . ? C28 C25 C26 108.7(3) . . ? C28 C25 C27 108.2(3) . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26B 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C25 C27 H27A 109.5 . . ? C25 C27 H27B 109.5 . . ? C25 C27 H27C 109.5 . . ? H27A C27 H27B 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C25 C28 H28A 109.5 . . ? C25 C28 H28B 109.5 . . ? C25 C28 H28C 109.5 . . ? H28A C28 H28B 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C31 I31 O1 173.71(9) . . ? C32 C31 I31 121.4(2) . . ? C36 C31 I31 121.5(2) . . ? C36 C31 C32 117.1(3) . . ? F31 C32 C31 120.3(3) . . ? F31 C32 C33 117.6(3) . . ? C33 C32 C31 122.1(3) . . ? F32 C33 C32 121.0(3) . . ? F32 C33 C34 119.5(3) . . ? C34 C33 C32 119.4(3) . . ? F33 C34 C33 120.2(3) . . ? F33 C34 C35 120.3(3) . . ? C33 C34 C35 119.5(3) . . ? F34 C35 C34 119.9(3) . . ? F34 C35 C36 120.3(3) . . ? C36 C35 C34 119.8(3) . . ? F35 C36 C31 120.6(2) . . ? F35 C36 C35 117.4(3) . . ? C35 C36 C31 122.0(3) . . ? C41 I41 O2 177.13(9) . . ? C42 C41 I41 121.5(2) . . ? C42 C41 C46 116.9(3) . . ? C46 C41 I41 121.7(2) . . ? F41 C42 C41 120.2(3) . . ? F41 C42 C43 118.0(3) . . ? C41 C42 C43 121.8(3) . . ? F42 C43 C42 119.4(3) . . ? F42 C43 C44 120.7(3) . . ? C44 C43 C42 119.9(3) . . ? F43 C44 C43 120.3(3) . . ? F43 C44 C45 119.8(3) . . ? C43 C44 C45 119.9(3) . . ? F44 C45 C44 120.1(3) . . ? F44 C45 C46 120.2(3) . . ? C44 C45 C46 119.6(3) . . ? F45 C46 C41 120.1(3) . . ? F45 C46 C45 118.0(3) . . ? C45 C46 C41 121.9(3) . . ? C51 I51 N6 169.32(9) . . ? C52 C51 I51 119.7(2) . . ? C56 C51 I51 122.6(2) . . ? C56 C51 C52 117.7(3) . . ? F51 C52 C51 120.7(3) . . ? F51 C52 C53 118.1(3) . . ? C53 C52 C51 121.2(3) . . ? F52 C53 C52 119.9(3) . . ? F52 C53 C54 120.4(3) . . ? C54 C53 C52 119.7(3) . . ? F53 C54 C53 119.9(3) . . ? F53 C54 C55 119.8(3) . . ? C53 C54 C55 120.3(3) . . ? F54 C55 C54 119.7(3) . . ? F54 C55 C56 121.0(3) . . ? C54 C55 C56 119.2(3) . . ? F55 C56 C51 120.4(3) . . ? F55 C56 C55 117.8(3) . . ? C51 C56 C55 121.8(3) . . ? 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 C4 C5 N4 -54.0(3) . . . . ? N1 C4 C5 C6 125.9(3) . . . . ? N4 C5 C6 C7 1.1(4) . . . . ? N4 C9 C10 N5 47.9(3) . . . . ? N6 I51 C51 C52 -35.5(6) . . . . ? N6 I51 C51 C56 143.1(4) . . . . ? N7 C14 C15 N8 -46.6(4) . . . . ? N7 C14 C15 C16 135.3(3) . . . . ? N8 C15 C16 C17 0.1(4) . . . . ? N8 C19 C20 N3 37.8(4) . . . . ? C1 N1 C2 N2 -39.5(3) . . . . ? C1 N1 C4 C5 -64.1(3) . . . . ? C1 N3 C3 N2 24.5(4) . . . . ? C1 N3 C20 C19 73.0(3) . . . . ? C2 N1 C1 O1 -173.8(2) . . . . ? C2 N1 C1 N3 7.7(4) . . . . ? C2 N1 C4 C5 106.6(3) . . . . ? C2 N2 C3 N3 -53.3(3) . . . . ? C2 N2 C21 C22 87.1(3) . . . . ? C2 N2 C21 C23 -36.0(4) . . . . ? C2 N2 C21 C24 -151.6(3) . . . . ? C3 N2 C2 N1 61.0(3) . . . . ? C3 N2 C21 C22 -44.1(4) . . . . ? C3 N2 C21 C23 -167.1(3) . . . . ? C3 N2 C21 C24 77.2(3) . . . . ? C3 N3 C1 O1 -178.9(2) . . . . ? C3 N3 C1 N1 -0.4(4) . . . . ? C3 N3 C20 C19 -103.2(3) . . . . ? C4 N1 C1 O1 -3.0(4) . . . . ? C4 N1 C1 N3 178.5(2) . . . . ? C4 N1 C2 N2 150.0(2) . . . . ? C4 C5 C6 C7 -178.8(3) . . . . ? C5 N4 C9 C8 0.2(4) . . . . ? C5 N4 C9 C10 179.5(2) . . . . ? C5 C6 C7 C8 0.9(4) . . . . ? C6 C7 C8 C9 -2.2(4) . . . . ? C7 C8 C9 N4 1.7(4) . . . . ? C7 C8 C9 C10 -177.6(3) . . . . ? C8 C9 C10 N5 -132.8(3) . . . . ? C9 N4 C5 C4 178.3(2) . . . . ? C9 N4 C5 C6 -1.6(4) . . . . ? C10 N5 C11 O2 10.9(4) . . . . ? C10 N5 C11 N7 -171.6(2) . . . . ? C10 N5 C12 N6 -158.1(2) . . . . ? C11 N5 C10 C9 66.1(3) . . . . ? C11 N5 C12 N6 41.1(3) . . . . ? C11 N7 C13 N6 -24.1(4) . . . . ? C11 N7 C14 C15 -69.8(3) . . . . ? C12 N5 C10 C9 -95.1(3) . . . . ? C12 N5 C11 O2 172.1(2) . . . . ? C12 N5 C11 N7 -10.4(3) . . . . ? C12 N6 C13 N7 51.2(3) . . . . ? C12 N6 C25 C26 -78.1(3) . . . . ? C12 N6 C25 C27 160.8(3) . . . . ? C12 N6 C25 C28 44.0(3) . . . . ? C12 N6 I51 C51 76.9(5) . . . . ? C13 N6 C12 N5 -59.8(3) . . . . ? C13 N6 C25 C26 51.1(3) . . . . ? C13 N6 C25 C27 -70.0(3) . . . . ? C13 N6 C25 C28 173.2(2) . . . . ? C13 N6 I51 C51 -32.0(5) . . . . ? C13 N7 C11 O2 179.4(2) . . . . ? C13 N7 C11 N5 1.9(4) . . . . ? C13 N7 C14 C15 109.7(3) . . . . ? C14 N7 C11 O2 -1.2(4) . . . . ? C14 N7 C11 N5 -178.7(2) . . . . ? C14 N7 C13 N6 156.5(2) . . . . ? C14 C15 C16 C17 178.1(3) . . . . ? C15 N8 C19 C18 1.7(4) . . . . ? C15 N8 C19 C20 -179.7(2) . . . . ? C15 C16 C17 C18 0.2(4) . . . . ? C16 C17 C18 C19 0.4(4) . . . . ? C17 C18 C19 N8 -1.4(4) . . . . ? C17 C18 C19 C20 180.0(3) . . . . ? C18 C19 C20 N3 -143.5(3) . . . . ? C19 N8 C15 C14 -179.0(2) . . . . ? C19 N8 C15 C16 -1.0(4) . . . . ? C20 N3 C1 O1 5.0(4) . . . . ? C20 N3 C1 N1 -176.5(2) . . . . ? C20 N3 C3 N2 -159.4(2) . . . . ? C21 N2 C2 N1 -73.9(3) . . . . ? C21 N2 C3 N3 83.6(3) . . . . ? C25 N6 C12 N5 73.8(3) . . . . ? C25 N6 C13 N7 -83.2(3) . . . . ? C25 N6 I51 C51 -157.9(5) . . . . ? I31 O1 C1 N1 -94.2(3) . . . . ? I31 O1 C1 N3 84.3(3) . . . . ? I31 C31 C32 F31 -1.8(4) . . . . ? I31 C31 C32 C33 179.1(2) . . . . ? I31 C31 C36 F35 -0.1(4) . . . . ? I31 C31 C36 C35 179.6(2) . . . . ? F31 C32 C33 F32 0.6(4) . . . . ? F31 C32 C33 C34 -177.3(3) . . . . ? F32 C33 C34 F33 0.9(5) . . . . ? F32 C33 C34 C35 -178.0(3) . . . . ? F33 C34 C35 F34 -0.7(4) . . . . ? F33 C34 C35 C36 -180.0(3) . . . . ? F34 C35 C36 F35 1.1(4) . . . . ? F34 C35 C36 C31 -178.6(2) . . . . ? C31 C32 C33 F32 179.7(3) . . . . ? C31 C32 C33 C34 1.8(5) . . . . ? C32 C31 C36 F35 -178.8(2) . . . . ? C32 C31 C36 C35 1.0(4) . . . . ? C32 C33 C34 F33 178.7(3) . . . . ? C32 C33 C34 C35 -0.1(5) . . . . ? C33 C34 C35 F34 178.2(3) . . . . ? C33 C34 C35 C36 -1.1(5) . . . . ? C34 C35 C36 F35 -179.6(3) . . . . ? C34 C35 C36 C31 0.7(4) . . . . ? C36 C31 C32 F31 176.8(2) . . . . ? C36 C31 C32 C33 -2.2(4) . . . . ? I41 O2 C11 N5 84.0(3) . . . . ? I41 O2 C11 N7 -93.4(3) . . . . ? I41 C41 C42 F41 -1.3(4) . . . . ? I41 C41 C42 C43 178.4(2) . . . . ? I41 C41 C46 F45 1.0(4) . . . . ? I41 C41 C46 C45 -179.4(2) . . . . ? F41 C42 C43 F42 1.9(4) . . . . ? F41 C42 C43 C44 -179.1(3) . . . . ? F42 C43 C44 F43 -0.1(5) . . . . ? F42 C43 C44 C45 178.5(3) . . . . ? F43 C44 C45 F44 -1.7(5) . . . . ? F43 C44 C45 C46 178.1(3) . . . . ? F44 C45 C46 F45 0.2(5) . . . . ? F44 C45 C46 C41 -179.4(3) . . . . ? C41 C42 C43 F42 -177.8(3) . . . . ? C41 C42 C43 C44 1.2(5) . . . . ? C42 C41 C46 F45 -179.7(3) . . . . ? C42 C41 C46 C45 -0.1(5) . . . . ? C42 C43 C44 F43 -179.1(3) . . . . ? C42 C43 C44 C45 -0.5(5) . . . . ? C43 C44 C45 F44 179.7(3) . . . . ? C43 C44 C45 C46 -0.5(5) . . . . ? C44 C45 C46 F45 -179.6(3) . . . . ? C44 C45 C46 C41 0.8(5) . . . . ? C46 C41 C42 F41 179.3(3) . . . . ? C46 C41 C42 C43 -0.9(4) . . . . ? I51 N6 C12 N5 -164.55(19) . . . . ? I51 N6 C13 N7 152.72(18) . . . . ? I51 N6 C25 C26 168.9(2) . . . . ? I51 N6 C25 C27 47.8(3) . . . . ? I51 N6 C25 C28 -69.0(2) . . . . ? I51 C51 C52 F51 -3.6(4) . . . . ? I51 C51 C52 C53 175.4(2) . . . . ? I51 C51 C56 F55 2.7(4) . . . . ? I51 C51 C56 C55 -176.7(2) . . . . ? F51 C52 C53 F52 0.1(4) . . . . ? F51 C52 C53 C54 -178.4(3) . . . . ? F52 C53 C54 F53 -0.4(4) . . . . ? F52 C53 C54 C55 -179.0(3) . . . . ? F53 C54 C55 F54 -1.0(4) . . . . ? F53 C54 C55 C56 -179.3(3) . . . . ? F54 C55 C56 F55 2.3(5) . . . . ? F54 C55 C56 C51 -178.3(3) . . . . ? C51 C52 C53 F52 -179.0(3) . . . . ? C51 C52 C53 C54 2.6(4) . . . . ? C52 C51 C56 F55 -178.7(3) . . . . ? C52 C51 C56 C55 1.9(4) . . . . ? C52 C53 C54 F53 178.1(3) . . . . ? C52 C53 C54 C55 -0.5(4) . . . . ? C53 C54 C55 F54 177.6(3) . . . . ? C53 C54 C55 C56 -0.8(5) . . . . ? C54 C55 C56 F55 -179.4(3) . . . . ? C54 C55 C56 C51 0.0(5) . . . . ? C56 C51 C52 F51 177.7(3) . . . . ? C56 C51 C52 C53 -3.2(4) . . . . ? _vrf_PLAT431_mg177s ; PROBLEM: Short Inter HL..A Contact I31 .. O1 . 2.72 Ang. RESPONSE: These are genuine contacts. The anisotropic displacement parameters of the iodine and oxygen atoms involved are normal, indicating no atom assignment errors, and there is no unusual residual electron density in the vicinity of the atoms involved. These are O---I halogen bonds, primarily electrostatic in nature, which are strenghthened by the five fluoro substituents on the iodine Shorter I-O distances have been observed previously, see: J. Am. Chem. Soc. 2003, 125, 13006 (2.598(2) Angstrom) Org. Lett. 2011, 13, 4324 (2.668 Ang) ; _database_code_depnum_ccdc_archive 'CCDC 947145' ####################################################################### # # 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_mgiv023s _audit_creation_date 2012-11-30 _audit_creation_method ; Olex2 1.1 (compiled Nov 1 2011 20:42:30, GUI svn.r3906) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C28 H40 N8 O2, C2 F4 I2' _chemical_formula_sum 'C30 H40 F4 I2 N8 O2' _chemical_formula_weight 874.50 _chemical_melting_point ? 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' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' _cell_length_a 9.372(2) _cell_length_b 9.757(2) _cell_length_c 10.799(3) _cell_angle_alpha 77.105(4) _cell_angle_beta 84.963(4) _cell_angle_gamma 63.533(4) _cell_volume 861.7(3) _cell_formula_units_Z 1 _cell_measurement_reflns_used 4619 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 26.404 _cell_measurement_theta_min 2.428 _exptl_absorpt_coefficient_mu 1.887 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_correction_T_min 0.746838 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS v.2.10 (Bruker,2003) was used for absorption correction. R(int) was 0.0630 before and 0.0377 after correction. The Ratio of minimum to maximum transmission is 0.7468. The \l/2 correction factor is 0.0015. ; _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.685 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 434 _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.15 _exptl_special_details ; The data collection nominally covered a full sphere of reciprocal space by a combination of 5 sets of \w and \f scans each set at different \f and/or \w angles and each scan (8 s exposure) covering -0.500\% degrees. The crystal to detector distance was 4.94 cm. ; _diffrn_reflns_av_R_equivalents 0.0407 _diffrn_reflns_av_unetI/netI 0.0407 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 11871 _diffrn_reflns_theta_full 26.66 _diffrn_reflns_theta_max 26.66 _diffrn_reflns_theta_min 1.93 _diffrn_ambient_temperature 100(2) _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.991 _diffrn_measured_fraction_theta_max 0.991 _diffrn_measurement_device_type 'Bruker SMART APEX CCD diffractometer' _diffrn_measurement_method 'omega and phi scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'sealed tube' _diffrn_source_current 37.0 _diffrn_source_power 1.776 _diffrn_source_target Mo _diffrn_source_voltage 48.0 _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 3302 _reflns_number_total 3607 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'SAINT-Plus Version 6.45 (Bruker, 2001)' _computing_data_collection 'SMART Version 5.625 (Bruker, 2001)' _computing_data_reduction 'SAINT-Plus Version 6.45 (Bruker, 2001)' _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. 2008). A64, 112-122 ; _computing_structure_solution ; SHELXS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 1.849 _refine_diff_density_min -0.425 _refine_diff_density_rms 0.124 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 211 _refine_ls_number_reflns 3607 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0375 _refine_ls_R_factor_gt 0.0335 _refine_ls_restrained_S_all 1.044 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0495P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0793 _refine_ls_wR_factor_ref 0.0814 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 O1 O 0.2982(3) 0.3114(3) 0.5406(2) 0.0294(6) Uani 1 1 d . . . N1 N 0.2051(3) 0.5570(3) 0.4160(3) 0.0243(6) Uani 1 1 d . . . N2 N 0.4257(3) 0.3534(3) 0.3566(3) 0.0227(6) Uani 1 1 d . . . N3 N 0.2950(3) 0.5957(3) 0.1996(3) 0.0236(6) Uani 1 1 d . . . N4 N 0.2581(3) 0.7255(3) 0.5688(3) 0.0243(6) Uani 1 1 d . . . C1 C 0.3113(4) 0.4030(4) 0.4442(3) 0.0232(7) Uani 1 1 d . . . C2 C 0.4408(4) 0.4577(4) 0.2392(3) 0.0266(7) Uani 1 1 d . . . H2A H 0.5237 0.4897 0.2529 0.032 Uiso 1 1 calc R . . H2B H 0.4771 0.3985 0.1700 0.032 Uiso 1 1 calc R . . C3 C 0.2327(4) 0.6643(4) 0.3088(3) 0.0281(7) Uani 1 1 d . . . H3A H 0.1309 0.7588 0.2848 0.034 Uiso 1 1 calc R . . H3B H 0.3084 0.6976 0.3359 0.034 Uiso 1 1 calc R . . C4 C 0.0835(4) 0.6254(4) 0.5067(3) 0.0290(8) Uani 1 1 d . . . H4A H 0.0760 0.5397 0.5718 0.035 Uiso 1 1 calc R . . H4B H -0.0206 0.6858 0.4615 0.035 Uiso 1 1 calc R . . C5 C 0.1127(4) 0.7318(4) 0.5732(3) 0.0243(7) Uani 1 1 d . . . C6 C -0.0120(4) 0.8289(4) 0.6400(3) 0.0274(7) Uani 1 1 d . . . H6 H -0.1153 0.8333 0.6393 0.033 Uiso 1 1 calc R . . C7 C 0.0188(4) 0.9179(4) 0.7067(4) 0.0318(8) Uani 1 1 d . . . H7 H -0.0626 0.9825 0.7552 0.038 Uiso 1 1 calc R . . C8 C 0.1701(5) 0.9124(4) 0.7023(3) 0.0296(8) Uani 1 1 d . . . H8 H 0.1933 0.9737 0.7471 0.036 Uiso 1 1 calc R . . C9 C 0.2855(4) 0.8164(4) 0.6319(3) 0.0238(7) Uani 1 1 d . . . C10 C 0.4510(4) 0.8069(4) 0.6210(3) 0.0276(7) Uani 1 1 d . . . H10A H 0.4638 0.8619 0.5349 0.033 Uiso 1 1 calc R . . H10B H 0.4643 0.8612 0.6832 0.033 Uiso 1 1 calc R . . C11 C 0.1838(4) 0.5808(4) 0.1166(3) 0.0266(7) Uani 1 1 d . . . C12 C 0.1489(5) 0.4388(5) 0.1684(3) 0.0327(8) Uani 1 1 d . . . H12A H 0.2493 0.3430 0.1813 0.049 Uiso 1 1 calc R . . H12B H 0.0814 0.4329 0.1073 0.049 Uiso 1 1 calc R . . H12C H 0.0935 0.4502 0.2495 0.049 Uiso 1 1 calc R . . C13 C 0.2613(4) 0.5672(5) -0.0137(3) 0.0318(8) Uani 1 1 d . . . H13A H 0.2829 0.6579 -0.0473 0.048 Uiso 1 1 calc R . . H13B H 0.1890 0.5638 -0.0719 0.048 Uiso 1 1 calc R . . H13C H 0.3615 0.4712 -0.0052 0.048 Uiso 1 1 calc R . . C14 C 0.0278(5) 0.7300(5) 0.0989(4) 0.0438(10) Uani 1 1 d . . . H14A H -0.0292 0.7368 0.1795 0.066 Uiso 1 1 calc R . . H14B H -0.0383 0.7283 0.0343 0.066 Uiso 1 1 calc R . . H14C H 0.0505 0.8210 0.0714 0.066 Uiso 1 1 calc R . . I1 I 0.43167(2) 0.17543(2) 0.778545(18) 0.02336(9) Uani 1 1 d . . . F1 F 0.6933(3) -0.0323(3) 0.9526(2) 0.0535(7) Uani 1 1 d . . . F2 F 0.5198(4) 0.1563(3) 1.0355(2) 0.0524(7) Uani 1 1 d . . . C15 C 0.5357(4) 0.0537(4) 0.9642(3) 0.0254(7) 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 O1 0.0341(14) 0.0399(15) 0.0189(12) 0.0018(11) -0.0024(10) -0.0235(12) N1 0.0301(15) 0.0274(15) 0.0214(14) -0.0070(12) 0.0030(11) -0.0174(12) N2 0.0222(14) 0.0253(14) 0.0213(14) -0.0037(11) 0.0003(11) -0.0114(12) N3 0.0268(15) 0.0273(15) 0.0196(14) -0.0022(12) 0.0007(11) -0.0157(12) N4 0.0249(14) 0.0234(14) 0.0255(15) -0.0075(12) -0.0006(11) -0.0102(12) C1 0.0251(17) 0.0311(18) 0.0199(16) -0.0019(14) -0.0039(13) -0.0189(14) C2 0.0271(18) 0.0348(19) 0.0171(16) -0.0012(14) 0.0013(13) -0.0149(15) C3 0.0368(19) 0.0243(17) 0.0283(18) -0.0064(14) -0.0005(15) -0.0171(15) C4 0.0271(18) 0.039(2) 0.0293(19) -0.0147(16) 0.0057(14) -0.0186(16) C5 0.0234(17) 0.0260(17) 0.0228(17) -0.0039(13) -0.0007(13) -0.0106(14) C6 0.0261(18) 0.0220(17) 0.0318(19) -0.0029(14) 0.0040(14) -0.0104(14) C7 0.036(2) 0.0225(18) 0.034(2) -0.0084(15) 0.0120(16) -0.0102(16) C8 0.044(2) 0.0218(17) 0.0256(18) -0.0081(14) 0.0009(15) -0.0149(16) C9 0.0277(17) 0.0215(16) 0.0203(16) -0.0013(13) -0.0037(13) -0.0099(14) C10 0.0324(19) 0.0237(17) 0.0302(19) -0.0063(14) -0.0021(15) -0.0148(15) C11 0.0245(17) 0.0337(19) 0.0218(17) -0.0034(14) -0.0019(13) -0.0138(15) C12 0.040(2) 0.051(2) 0.0208(17) -0.0061(16) 0.0006(15) -0.0318(19) C13 0.0308(19) 0.041(2) 0.0216(17) -0.0035(15) 0.0006(14) -0.0149(17) C14 0.030(2) 0.049(3) 0.042(2) -0.012(2) -0.0071(18) -0.0065(18) I1 0.02874(14) 0.02334(13) 0.01988(13) -0.00066(9) -0.00168(9) -0.01447(10) F1 0.0251(12) 0.0742(18) 0.0410(14) 0.0190(13) -0.0035(10) -0.0176(12) F2 0.103(2) 0.0369(13) 0.0332(13) 0.0027(10) -0.0211(13) -0.0452(14) C15 0.0280(18) 0.0263(18) 0.0239(17) -0.0035(14) -0.0023(14) -0.0138(15) _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 O1 C1 1.248(4) . ? O1 I1 2.737(2) . ? N1 C1 1.363(4) . ? N1 C3 1.467(4) . ? N1 C4 1.456(4) . ? N2 C1 1.357(4) . ? N2 C2 1.479(4) . ? N2 C10 1.453(4) 2_666 ? N3 C2 1.438(4) . ? N3 C3 1.436(4) . ? N3 C11 1.505(4) . ? N4 C5 1.333(4) . ? N4 C9 1.349(4) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C4 C5 1.513(5) . ? C5 C6 1.398(5) . ? C6 H6 0.9500 . ? C6 C7 1.377(5) . ? C7 H7 0.9500 . ? C7 C8 1.393(5) . ? C8 H8 0.9500 . ? C8 C9 1.377(5) . ? C9 C10 1.508(5) . ? C10 N2 1.453(4) 2_666 ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.538(5) . ? C11 C13 1.531(5) . ? C11 C14 1.524(5) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? I1 C15 2.151(3) . ? F1 C15 1.346(4) . ? F2 C15 1.345(4) . ? C15 C15 1.522(7) 2_657 ? 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 C1 O1 I1 138.2(2) . . ? C1 N1 C3 120.4(3) . . ? C1 N1 C4 120.5(3) . . ? C4 N1 C3 117.6(3) . . ? C1 N2 C2 123.4(3) . . ? C1 N2 C10 120.5(3) . 2_666 ? C10 N2 C2 115.9(3) 2_666 . ? C2 N3 C11 116.5(3) . . ? C3 N3 C2 107.1(3) . . ? C3 N3 C11 119.1(3) . . ? C5 N4 C9 118.4(3) . . ? O1 C1 N1 122.0(3) . . ? O1 C1 N2 122.1(3) . . ? N2 C1 N1 115.8(3) . . ? N2 C2 H2A 108.8 . . ? N2 C2 H2B 108.8 . . ? N3 C2 N2 113.6(3) . . ? N3 C2 H2A 108.8 . . ? N3 C2 H2B 108.8 . . ? H2A C2 H2B 107.7 . . ? N1 C3 H3A 109.0 . . ? N1 C3 H3B 109.0 . . ? N3 C3 N1 113.0(3) . . ? N3 C3 H3A 109.0 . . ? N3 C3 H3B 109.0 . . ? H3A C3 H3B 107.8 . . ? N1 C4 H4A 108.6 . . ? N1 C4 H4B 108.6 . . ? N1 C4 C5 114.8(3) . . ? H4A C4 H4B 107.5 . . ? C5 C4 H4A 108.6 . . ? C5 C4 H4B 108.6 . . ? N4 C5 C4 118.5(3) . . ? N4 C5 C6 122.7(3) . . ? C6 C5 C4 118.8(3) . . ? C5 C6 H6 120.9 . . ? C7 C6 C5 118.3(3) . . ? C7 C6 H6 120.9 . . ? C6 C7 H7 120.3 . . ? C6 C7 C8 119.4(3) . . ? C8 C7 H7 120.3 . . ? C7 C8 H8 120.7 . . ? C9 C8 C7 118.7(3) . . ? C9 C8 H8 120.7 . . ? N4 C9 C8 122.5(3) . . ? N4 C9 C10 116.0(3) . . ? C8 C9 C10 121.5(3) . . ? N2 C10 C9 112.4(3) 2_666 . ? N2 C10 H10A 109.1 2_666 . ? N2 C10 H10B 109.1 2_666 . ? C9 C10 H10A 109.1 . . ? C9 C10 H10B 109.1 . . ? H10A C10 H10B 107.8 . . ? N3 C11 C12 114.0(3) . . ? N3 C11 C13 107.2(3) . . ? N3 C11 C14 109.1(3) . . ? C13 C11 C12 109.2(3) . . ? C14 C11 C12 109.5(3) . . ? C14 C11 C13 107.7(3) . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12B 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C11 C13 H13A 109.5 . . ? C11 C13 H13B 109.5 . . ? C11 C13 H13C 109.5 . . ? H13A C13 H13B 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C11 C14 H14A 109.5 . . ? C11 C14 H14B 109.5 . . ? C11 C14 H14C 109.5 . . ? H14A C14 H14B 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C15 I1 O1 175.94(10) . . ? F1 C15 I1 109.1(2) . . ? F1 C15 C15 108.5(3) . 2_657 ? F2 C15 I1 110.4(2) . . ? F2 C15 F1 106.4(3) . . ? F2 C15 C15 108.4(4) . 2_657 ? C15 C15 I1 113.7(3) 2_657 . ? 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 C4 C5 N4 -15.8(5) . . . . ? N1 C4 C5 C6 166.1(3) . . . . ? N4 C5 C6 C7 -2.0(5) . . . . ? N4 C9 C10 N2 -47.9(4) . . . 2_666 ? C1 N1 C3 N3 40.1(4) . . . . ? C1 N1 C4 C5 106.3(4) . . . . ? C1 N2 C2 N3 -23.3(4) . . . . ? C2 N2 C1 O1 177.7(3) . . . . ? C2 N2 C1 N1 2.0(4) . . . . ? C2 N3 C3 N1 -57.6(4) . . . . ? C2 N3 C11 C12 49.9(4) . . . . ? C2 N3 C11 C13 -71.1(4) . . . . ? C2 N3 C11 C14 172.6(3) . . . . ? C3 N1 C1 O1 174.1(3) . . . . ? C3 N1 C1 N2 -10.2(4) . . . . ? C3 N1 C4 C5 -60.0(4) . . . . ? C3 N3 C2 N2 49.3(4) . . . . ? C3 N3 C11 C12 -80.9(4) . . . . ? C3 N3 C11 C13 158.1(3) . . . . ? C3 N3 C11 C14 41.7(4) . . . . ? C4 N1 C1 O1 8.2(5) . . . . ? C4 N1 C1 N2 -176.1(3) . . . . ? C4 N1 C3 N3 -153.6(3) . . . . ? C4 C5 C6 C7 176.0(3) . . . . ? C5 N4 C9 C8 1.3(5) . . . . ? C5 N4 C9 C10 -178.7(3) . . . . ? C5 C6 C7 C8 2.0(5) . . . . ? C6 C7 C8 C9 -0.6(5) . . . . ? C7 C8 C9 N4 -1.2(5) . . . . ? C7 C8 C9 C10 178.8(3) . . . . ? C8 C9 C10 N2 132.1(3) . . . 2_666 ? C9 N4 C5 C4 -177.7(3) . . . . ? C9 N4 C5 C6 0.3(5) . . . . ? C10 N2 C1 O1 -6.8(5) 2_666 . . . ? C10 N2 C1 N1 177.6(3) 2_666 . . . ? C10 N2 C2 N3 160.9(3) 2_666 . . . ? C11 N3 C2 N2 -87.0(3) . . . . ? C11 N3 C3 N1 77.2(4) . . . . ? I1 O1 C1 N1 -101.7(4) . . . . ? I1 O1 C1 N2 82.9(4) . . . . ? _vrf_PLAT431_mgiv023s ; PROBLEM: Short Inter HL..A Contact I1 .. O1 . 2.74 Ang. RESPONSE: These are genuine I---O halogen bonds. The anisotropic displacement parameters of the iodine and oxygen atoms involved are normal, indicating no atom assignment errors, and there is no unusual residual electron density in the vicinity of the atoms involved. These are I---O halogen bonds, primarily electrostatic in nature, which are strenghthened by the fluoro substituents on the C2F4I2 ligand. Shorter I-O distances have been observed previously, see: J. Am. Chem. Soc. 2003, 125, 13006 (2.598(2) Angstrom) Org. Lett. 2011, 13, 4324 (2.668 Ang) ; _database_code_depnum_ccdc_archive 'CCDC 947146' ####################################################################### # # 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_mg143as _audit_creation_date 2012-09-10 _audit_creation_method ; Olex2 1.2 (compiled May 9 2012 12:37:22, GUI svn.r4230) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C28 H38 N8 O2, 2(I), 2(C2 F4 I2)' _chemical_formula_sum 'C32 H38 F8 I6 N8 O2' _chemical_formula_weight 1480.11 _chemical_melting_point ? 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' _cell_length_a 8.3319(15) _cell_length_b 11.289(2) _cell_length_c 13.162(2) _cell_angle_alpha 84.680(4) _cell_angle_beta 80.485(4) _cell_angle_gamma 74.665(4) _cell_volume 1176.0(4) _cell_formula_units_Z 1 _cell_measurement_reflns_used 2405 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 23.09 _cell_measurement_theta_min 2.38 _exptl_absorpt_coefficient_mu 4.031 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_correction_T_min 0.746787 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS v.2.10 (Bruker,2003) was used for absorption correction. R(int) was 0.0593 before and 0.0369 after correction. The Ratio of minimum to maximum transmission is 0.7468. The \l/2 correction factor is 0.0015. ; _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 2.090 _exptl_crystal_density_meas . _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 692 _exptl_crystal_recrystallization_method 'Slow evaporation from CH2Cl2' _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.06 _exptl_special_details ; The data collection nominally covered a full sphere of reciprocal space by a combination of 5 sets of \w and \f scans each set at different \f and/or \w angles and each scan (20 s exposure) covering -0.300\% degrees. The crystal to detector distance was 4.954 cm. ; _diffrn_reflns_av_R_equivalents 0.0501 _diffrn_reflns_av_unetI/netI 0.0558 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 12706 _diffrn_reflns_theta_full 25.03 _diffrn_reflns_theta_max 25.03 _diffrn_reflns_theta_min 1.57 _diffrn_ambient_temperature 100(2) _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'sealed tube' _diffrn_source_current 39.0 _diffrn_source_power 1.833 _diffrn_source_target Mo _diffrn_source_voltage 47.0 _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 3251 _reflns_number_total 4154 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'SAINT-Plus Version 6.45 (Bruker, 2001)' _computing_data_collection 'SMART Version 5.625 (Bruker, 2001)' _computing_data_reduction 'SAINT-Plus Version 6.45 (Bruker, 2001)' _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _refine_diff_density_max 1.222 _refine_diff_density_min -0.834 _refine_diff_density_rms 0.164 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.091 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 296 _refine_ls_number_reflns 4154 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0701 _refine_ls_R_factor_gt 0.0497 _refine_ls_restrained_S_all 1.091 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0528P)^2^+3.5816P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1106 _refine_ls_wR_factor_ref 0.1191 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 O1 O 0.1941(7) 0.4524(5) 0.5792(4) 0.0269(13) Uani 1 1 d . . . N1 N 0.4213(8) 0.2890(5) 0.5898(5) 0.0212(14) Uani 1 1 d . . . N2 N 0.6032(8) 0.2359(5) 0.4323(5) 0.0220(14) Uani 1 1 d . . . N3 N 0.3347(8) 0.3554(5) 0.4326(5) 0.0196(14) Uani 1 1 d . . . N4 N 0.6207(8) 0.4280(5) 0.6671(5) 0.0224(14) Uani 1 1 d . . . C1 C 0.3071(10) 0.3705(6) 0.5406(6) 0.0216(17) Uani 1 1 d . . . C2 C 0.5338(10) 0.1881(6) 0.5325(6) 0.0242(18) Uani 1 1 d . . . H2A H 0.4717 0.1276 0.5222 0.029 Uiso 1 1 calc R . . H2B H 0.6263 0.1460 0.5718 0.029 Uiso 1 1 calc R . . C3 C 0.4912(10) 0.3102(6) 0.3840(6) 0.0226(17) Uani 1 1 d . . . H3 H 0.5196 0.3333 0.3134 0.027 Uiso 1 1 calc R . . C4 C 0.4296(10) 0.2975(7) 0.6987(6) 0.0219(17) Uani 1 1 d . . . H4A H 0.4169 0.2202 0.7372 0.026 Uiso 1 1 calc R . . H4B H 0.3364 0.3657 0.7275 0.026 Uiso 1 1 calc R . . C5 C 0.5962(10) 0.3202(7) 0.7111(6) 0.0229(17) Uani 1 1 d . . . C6 C 0.7114(11) 0.2359(8) 0.7638(6) 0.031(2) Uani 1 1 d . . . H6 H 0.6881 0.1617 0.7946 0.037 Uiso 1 1 calc R . . C7 C 0.8609(11) 0.2635(8) 0.7698(7) 0.032(2) Uani 1 1 d . . . H7 H 0.9441 0.2074 0.8040 0.038 Uiso 1 1 calc R . . C8 C 0.8891(10) 0.3736(7) 0.7257(6) 0.0274(18) Uani 1 1 d . . . H8 H 0.9903 0.3953 0.7303 0.033 Uiso 1 1 calc R . . C9 C 0.7658(10) 0.4516(7) 0.6748(6) 0.0216(17) Uani 1 1 d . . . C10 C 0.7956(9) 0.5737(7) 0.6280(6) 0.0219(17) Uani 1 1 d . . . H10A H 0.8014 0.6241 0.6843 0.026 Uiso 1 1 calc R . . H10B H 0.9058 0.5577 0.5830 0.026 Uiso 1 1 calc R . . C11 C 0.7886(10) 0.1896(7) 0.3911(6) 0.0261(18) Uani 1 1 d . . . C12 C 0.8267(10) 0.0494(7) 0.3887(7) 0.0282(19) Uani 1 1 d . . . H12A H 0.8027 0.0142 0.4588 0.042 Uiso 1 1 calc R . . H12B H 0.9455 0.0163 0.3615 0.042 Uiso 1 1 calc R . . H12C H 0.7561 0.0279 0.3444 0.042 Uiso 1 1 calc R . . C13 C 0.8896(10) 0.2279(7) 0.4622(7) 0.0282(19) Uani 1 1 d . . . H13A H 0.8548 0.3174 0.4668 0.042 Uiso 1 1 calc R . . H13B H 1.0096 0.2026 0.4347 0.042 Uiso 1 1 calc R . . H13C H 0.8698 0.1884 0.5310 0.042 Uiso 1 1 calc R . . C14 C 0.8234(11) 0.2464(8) 0.2821(6) 0.034(2) Uani 1 1 d . . . H14A H 0.7546 0.2233 0.2375 0.052 Uiso 1 1 calc R . . H14B H 0.9427 0.2161 0.2547 0.052 Uiso 1 1 calc R . . H14C H 0.7950 0.3362 0.2844 0.052 Uiso 1 1 calc R . . I1 I 0.35560(7) 0.08811(4) 0.28260(4) 0.02766(17) Uani 1 1 d . . . I2 I 0.29077(7) 0.00323(5) 0.90440(4) 0.03248(18) Uani 1 1 d . . . F1 F -0.0226(6) 0.1578(4) 1.0049(4) 0.0352(12) Uani 1 1 d . . . F2 F 0.0909(6) 0.0107(4) 1.1080(3) 0.0335(11) Uani 1 1 d . . . C21 C 0.0575(11) 0.0372(7) 1.0103(6) 0.0270(18) Uani 1 1 d . . . I11 I 0.7784(7) 0.6804(3) 0.9081(2) 0.0490(10) Uani 0.268(3) 1 d P . . I12 I 0.6858(17) 0.6780(3) 0.9156(3) 0.0304(13) Uiso 0.220(7) 1 d P . . I13 I 0.620(2) 0.6729(3) 0.9079(3) 0.0230(13) Uiso 0.239(7) 1 d P . . I14 I 0.5601(12) 0.6650(3) 0.9066(2) 0.0224(13) Uiso 0.201(8) 1 d P . . I15 I 0.3890(9) 0.5695(6) 0.9498(6) 0.023(3) Uiso 0.072(2) 1 d P . . F11 F 0.339(2) 0.5928(13) 1.0265(12) 0.0370(17) Uiso 0.335(4) 1 d P . . F12 F 0.239(3) 0.5824(14) 1.0224(13) 0.0370(17) Uiso 0.305(11) 1 d P . . F13 F 0.359(2) 0.4663(14) 0.8920(12) 0.0370(17) Uiso 0.315(11) 1 d P . . F14 F 0.451(2) 0.4863(15) 0.9032(13) 0.0370(17) Uiso 0.303(11) 1 d P . . F15 F 0.066(3) 0.532(2) 0.8927(16) 0.0370(17) Uiso 0.228(10) 1 d P . . F16 F 0.123(4) 0.439(3) 0.895(2) 0.0370(17) Uiso 0.176(10) 1 d P . . F17 F 0.160(4) 0.571(2) 0.993(2) 0.0370(17) Uiso 0.185(11) 1 d P . . F18 F -0.024(4) 0.414(3) 0.975(2) 0.0370(17) Uiso 0.152(10) 1 d P . . C31 C 0.636(5) 0.516(3) 1.007(2) 0.045(4) Uiso 0.322(4) 1 d P . . C32 C 0.459(3) 0.494(3) 0.996(2) 0.045(4) Uiso 0.424(15) 1 d P . . C33 C 0.101(5) 0.469(4) 0.986(3) 0.045(4) Uiso 0.254(15) 1 d P . . 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 O1 0.019(3) 0.021(3) 0.034(3) -0.004(2) 0.004(2) 0.003(2) N1 0.019(4) 0.021(3) 0.023(3) -0.001(3) 0.000(3) -0.007(3) N2 0.019(4) 0.019(3) 0.028(4) 0.000(3) -0.003(3) -0.005(3) N3 0.015(3) 0.017(3) 0.023(3) -0.002(3) 0.002(3) -0.001(3) N4 0.024(4) 0.019(3) 0.023(4) -0.003(3) 0.000(3) -0.006(3) C1 0.018(4) 0.014(4) 0.031(4) 0.002(3) 0.001(3) -0.006(3) C2 0.023(4) 0.015(4) 0.030(4) 0.004(3) -0.001(4) -0.001(3) C3 0.022(4) 0.019(4) 0.027(4) 0.004(3) -0.007(4) -0.006(3) C4 0.024(4) 0.020(4) 0.022(4) 0.001(3) -0.003(3) -0.008(3) C5 0.023(4) 0.027(4) 0.018(4) 0.000(3) -0.003(3) -0.004(3) C6 0.036(5) 0.030(4) 0.028(5) -0.003(4) -0.003(4) -0.012(4) C7 0.032(5) 0.031(4) 0.034(5) 0.011(4) -0.014(4) -0.008(4) C8 0.012(4) 0.027(4) 0.039(5) -0.003(4) -0.003(4) 0.000(3) C9 0.019(4) 0.023(4) 0.018(4) -0.002(3) 0.007(3) -0.002(3) C10 0.015(4) 0.024(4) 0.025(4) 0.004(3) -0.003(3) -0.004(3) C11 0.017(4) 0.022(4) 0.029(4) -0.003(3) 0.009(3) 0.006(3) C12 0.023(5) 0.021(4) 0.035(5) -0.002(4) 0.005(4) 0.000(3) C13 0.015(4) 0.028(4) 0.040(5) -0.006(4) 0.000(4) -0.002(3) C14 0.027(5) 0.034(5) 0.032(5) 0.003(4) 0.007(4) 0.000(4) I1 0.0243(3) 0.0219(3) 0.0342(3) -0.0022(2) -0.0001(2) -0.0038(2) I2 0.0308(3) 0.0360(3) 0.0294(3) 0.0004(2) 0.0009(2) -0.0103(3) F1 0.039(3) 0.024(2) 0.040(3) 0.000(2) 0.000(2) -0.006(2) F2 0.040(3) 0.044(3) 0.019(2) -0.001(2) -0.009(2) -0.010(2) C21 0.037(5) 0.023(4) 0.015(4) 0.003(3) 0.002(4) -0.002(4) I11 0.056(3) 0.0700(19) 0.0343(14) -0.0191(12) 0.0004(14) -0.0370(15) _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 O1 C1 1.211(9) . ? N1 C1 1.343(10) . ? N1 C2 1.451(9) . ? N1 C4 1.459(9) . ? N2 C2 1.465(10) . ? N2 C3 1.289(9) . ? N2 C11 1.517(9) . ? N3 C1 1.421(10) . ? N3 C3 1.342(10) . ? N3 C10 1.471(9) 2_666 ? N4 C5 1.350(9) . ? N4 C9 1.326(10) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 H3 0.9500 . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C4 C5 1.513(11) . ? C5 C6 1.386(11) . ? C6 H6 0.9500 . ? C6 C7 1.378(12) . ? C7 H7 0.9500 . ? C7 C8 1.383(11) . ? C8 H8 0.9500 . ? C8 C9 1.386(11) . ? C9 C10 1.520(10) . ? C10 N3 1.471(9) 2_666 ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.532(10) . ? C11 C13 1.516(11) . ? C11 C14 1.531(11) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? I2 C21 2.163(8) . ? F1 C21 1.349(8) . ? F2 C21 1.351(9) . ? C21 C21 1.500(17) 2_557 ? I11 I12 0.769(11) . ? I11 I13 1.344(17) . ? I11 I14 1.875(11) . ? I11 C33 2.22(4) 2_667 ? I12 I13 0.590(10) . ? I12 I14 1.121(13) . ? I12 I15 2.992(15) . ? I12 C31 2.19(3) . ? I12 C33 2.53(4) 2_667 ? I13 I14 0.534(10) . ? I13 I15 2.469(17) . ? I13 C31 2.09(3) . ? I13 C32 2.35(3) 2_667 ? I14 I15 1.988(12) . ? I14 I15 3.083(8) 2_667 ? I14 F14 2.43(2) . ? I14 C31 2.07(3) . ? I14 C32 2.13(3) 2_667 ? I14 C32 2.44(3) . ? I15 F11 1.056(16) . ? I15 F12 1.42(2) . ? I15 F13 1.542(18) . ? I15 F14 1.127(17) . ? I15 F14 2.469(19) 2_667 ? I15 F17 1.90(3) . ? I15 C31 1.12(3) 2_667 ? I15 C31 2.22(4) . ? I15 C32 1.54(3) 2_667 ? I15 C32 1.09(3) . ? F11 F12 0.88(2) . ? F11 F17 1.71(4) . ? F11 C31 1.29(3) 2_667 ? F11 C32 1.33(3) . ? F11 C32 1.70(3) 2_667 ? F12 F17 0.86(3) . ? F12 F18 1.78(4) 2_567 ? F12 C31 1.34(4) 2_667 ? F12 C32 1.83(3) . ? F13 F14 0.894(19) . ? F13 C31 1.37(4) 2_667 ? F13 C32 1.80(3) . ? F14 I15 2.469(19) 2_667 ? F14 C31 1.28(4) 2_667 ? F14 C32 1.69(3) 2_667 ? F14 C32 1.24(3) . ? F15 F16 1.03(3) . ? F15 C33 1.40(4) . ? F16 F18 1.55(4) . ? F16 C33 1.26(5) . ? F17 F18 1.11(4) 2_567 ? F17 C31 1.73(5) 2_667 ? F17 C33 1.38(5) . ? F18 F12 1.78(4) 2_567 ? F18 F17 1.11(4) 2_567 ? F18 C33 1.38(5) . ? F18 C33 1.40(5) 2_567 ? C31 I15 1.12(3) 2_667 ? C31 F11 1.29(3) 2_667 ? C31 F12 1.34(4) 2_667 ? C31 F13 1.37(4) 2_667 ? C31 F14 1.28(4) 2_667 ? C31 F17 1.73(5) 2_667 ? C31 C32 0.83(3) 2_667 ? C31 C32 1.59(5) . ? C32 I14 2.13(3) 2_667 ? C32 I15 1.54(3) 2_667 ? C32 F11 1.70(3) 2_667 ? C32 F14 1.69(3) 2_667 ? C32 C31 0.83(3) 2_667 ? C32 C32 0.76(5) 2_667 ? C33 I11 2.22(4) 2_667 ? C33 I12 2.53(4) 2_667 ? C33 F18 1.40(5) 2_567 ? C33 C33 1.64(8) 2_567 ? 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 C1 N1 C2 118.0(6) . . ? C1 N1 C4 121.6(6) . . ? C2 N1 C4 120.3(6) . . ? C2 N2 C11 120.1(6) . . ? C3 N2 C2 113.5(7) . . ? C3 N2 C11 126.2(7) . . ? C1 N3 C10 117.9(6) . 2_666 ? C3 N3 C1 120.0(6) . . ? C3 N3 C10 119.0(6) . 2_666 ? C9 N4 C5 116.6(7) . . ? O1 C1 N1 126.4(8) . . ? O1 C1 N3 121.1(7) . . ? N1 C1 N3 112.5(6) . . ? N1 C2 N2 109.4(6) . . ? N1 C2 H2A 109.8 . . ? N1 C2 H2B 109.8 . . ? N2 C2 H2A 109.8 . . ? N2 C2 H2B 109.8 . . ? H2A C2 H2B 108.2 . . ? N2 C3 N3 120.6(7) . . ? N2 C3 H3 119.7 . . ? N3 C3 H3 119.7 . . ? N1 C4 H4A 109.6 . . ? N1 C4 H4B 109.6 . . ? N1 C4 C5 110.2(6) . . ? H4A C4 H4B 108.1 . . ? C5 C4 H4A 109.6 . . ? C5 C4 H4B 109.6 . . ? N4 C5 C4 114.2(6) . . ? N4 C5 C6 123.9(7) . . ? C6 C5 C4 121.8(7) . . ? C5 C6 H6 121.1 . . ? C7 C6 C5 117.8(8) . . ? C7 C6 H6 121.1 . . ? C6 C7 H7 120.3 . . ? C6 C7 C8 119.5(8) . . ? C8 C7 H7 120.3 . . ? C7 C8 H8 120.9 . . ? C7 C8 C9 118.3(8) . . ? C9 C8 H8 120.9 . . ? N4 C9 C8 123.9(7) . . ? N4 C9 C10 117.9(7) . . ? C8 C9 C10 118.2(7) . . ? N3 C10 C9 114.1(6) 2_666 . ? N3 C10 H10A 108.7 2_666 . ? N3 C10 H10B 108.7 2_666 . ? C9 C10 H10A 108.7 . . ? C9 C10 H10B 108.7 . . ? H10A C10 H10B 107.6 . . ? N2 C11 C12 107.3(6) . . ? N2 C11 C14 109.0(6) . . ? C13 C11 N2 108.4(6) . . ? C13 C11 C12 111.7(7) . . ? C13 C11 C14 110.2(7) . . ? C14 C11 C12 110.3(7) . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12B 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C11 C13 H13A 109.5 . . ? C11 C13 H13B 109.5 . . ? C11 C13 H13C 109.5 . . ? H13A C13 H13B 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C11 C14 H14A 109.5 . . ? C11 C14 H14B 109.5 . . ? C11 C14 H14C 109.5 . . ? H14A C14 H14B 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? F1 C21 I2 109.9(5) . . ? F1 C21 F2 106.4(6) . . ? F1 C21 C21 109.3(8) . 2_557 ? F2 C21 I2 109.5(5) . . ? F2 C21 C21 109.0(8) . 2_557 ? C21 C21 I2 112.6(7) 2_557 . ? 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 C4 C5 N4 63.6(8) . . . . ? N1 C4 C5 C6 -116.6(8) . . . . ? N4 C5 C6 C7 -1.2(12) . . . . ? N4 C9 C10 N3 -7.6(10) . . . 2_666 ? C1 N1 C2 N2 47.2(9) . . . . ? C1 N1 C4 C5 -116.6(7) . . . . ? C1 N3 C3 N2 28.6(10) . . . . ? C2 N1 C1 O1 172.3(7) . . . . ? C2 N1 C1 N3 -10.1(9) . . . . ? C2 N1 C4 C5 65.8(8) . . . . ? C2 N2 C3 N3 12.4(10) . . . . ? C2 N2 C11 C12 55.9(9) . . . . ? C2 N2 C11 C13 -64.8(8) . . . . ? C2 N2 C11 C14 175.3(7) . . . . ? C3 N2 C2 N1 -47.9(9) . . . . ? C3 N2 C11 C12 -118.9(8) . . . . ? C3 N2 C11 C13 120.5(8) . . . . ? C3 N2 C11 C14 0.6(10) . . . . ? C3 N3 C1 O1 148.5(7) . . . . ? C3 N3 C1 N1 -29.3(9) . . . . ? C4 N1 C1 O1 -5.4(12) . . . . ? C4 N1 C1 N3 172.2(6) . . . . ? C4 N1 C2 N2 -135.1(7) . . . . ? C4 C5 C6 C7 179.0(7) . . . . ? C5 N4 C9 C8 -0.9(11) . . . . ? C5 N4 C9 C10 -178.7(6) . . . . ? C5 C6 C7 C8 1.3(12) . . . . ? C6 C7 C8 C9 -1.3(12) . . . . ? C7 C8 C9 N4 1.2(12) . . . . ? C7 C8 C9 C10 178.9(7) . . . . ? C8 C9 C10 N3 174.6(7) . . . 2_666 ? C9 N4 C5 C4 -179.2(6) . . . . ? C9 N4 C5 C6 0.9(11) . . . . ? C10 N3 C1 O1 -11.3(10) 2_666 . . . ? C10 N3 C1 N1 171.0(6) 2_666 . . . ? C10 N3 C3 N2 -171.9(6) 2_666 . . . ? C11 N2 C2 N1 136.7(7) . . . . ? C11 N2 C3 N3 -172.6(7) . . . . ? ###END _database_code_depnum_ccdc_archive 'CCDC 947147'