data_re88 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C40 H36 F16 I4 N6, 2(C12 H10 N2)' _chemical_formula_sum 'C64 H56 F16 I4 N10' _chemical_formula_weight 1776.79 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'F' 'F' 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'I' 'I' -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.6941(14) _cell_length_b 11.9320(18) _cell_length_c 32.228(5) _cell_angle_alpha 90.00 _cell_angle_beta 91.43(3) _cell_angle_gamma 90.00 _cell_volume 3342.2(9) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 5766 _cell_measurement_theta_min 2.412 _cell_measurement_theta_max 23.870 _exptl_crystal_description 'irregular prism' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.17 _exptl_crystal_density_diffrn 1.766 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1732 _exptl_absorpt_coefficient_mu 1.957 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS, Bruker, 1997' _exptl_absorpt_correction_T_min 0.636235 _exptl_absorpt_correction_T_max 0.716992 _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX' _diffrn_measurement_method 'phi and omega scans' _diffrn_standards_decay_% 0.00 _diffrn_reflns_number 44228 _diffrn_reflns_av_R_equivalents 0.0389 _diffrn_reflns_av_sigmaI/netI 0.0229 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -43 _diffrn_reflns_limit_l_max 43 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 29.04 _reflns_number_total 8884 _reflns_number_gt 6358 _reflns_threshold_expression 'I>2\s(I)' _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution ; M.C. Burla, M. Camalli, B. Carrozzini, G.L. Cascarano, C. Giacovazzo, G. Polidori, R. Spagna (2003). SIR2002: the program. J. Appl. Cryst. 36,1103 ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-III (Burnett and Johnson, 1996), Mercury 1.4, CCDC' _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. All H atoms were calculated, excluding H7 and H17 refined with restraints on the N-H distance. ; _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^)+(0.0642P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8884 _refine_ls_number_parameters 432 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0596 _refine_ls_R_factor_gt 0.0418 _refine_ls_wR_factor_ref 0.1109 _refine_ls_wR_factor_gt 0.1043 _refine_ls_goodness_of_fit_ref 0.956 _refine_ls_restrained_S_all 0.956 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I1 I 0.36771(2) 0.749360(17) 0.104004(7) 0.06906(9) Uani 1 1 d . . . I2 I 0.62568(3) -0.67115(2) 0.197115(8) 0.09125(12) Uani 1 1 d . . . F1 F 0.4883(2) 0.31131(12) 0.07886(6) 0.0685(5) Uani 1 1 d . . . F2 F 0.3376(2) 0.47978(17) 0.11267(6) 0.0825(6) Uani 1 1 d . . . F3 F 0.6248(2) 0.73716(13) 0.03557(8) 0.0790(6) Uani 1 1 d . . . F4 F 0.77159(19) 0.57359(14) 0.00001(6) 0.0690(5) Uani 1 1 d . . . F5 F 0.9844(2) -0.43911(14) 0.09220(5) 0.0651(4) Uani 1 1 d . . . F6 F 0.8575(2) -0.62492(17) 0.12184(7) 0.0814(5) Uani 1 1 d . . . F7 F 0.5879(3) -0.4126(2) 0.21927(8) 0.1166(9) Uani 1 1 d . . . F8 F 0.7100(3) -0.22890(19) 0.19167(8) 0.1036(8) Uani 1 1 d . . . C1 C 0.5388(3) 0.0250(2) 0.01857(9) 0.0465(6) Uani 1 1 d . . . H1A H 0.5355 -0.0280 0.0414 0.056 Uiso 1 1 calc R . . H1B H 0.4833 0.0917 0.0267 0.056 Uiso 1 1 calc R . . C2 C 0.7051(3) 0.0558(2) 0.01091(9) 0.0490(6) Uani 1 1 d . . . H2A H 0.7624 -0.0125 0.0060 0.059 Uiso 1 1 calc R . . H2B H 0.7085 0.1006 -0.0142 0.059 Uiso 1 1 calc R . . N3 N 0.7813(2) 0.11732(17) 0.04447(7) 0.0458(5) Uani 1 1 d . . . C4 C 0.9386(3) 0.1518(2) 0.03326(11) 0.0595(7) Uani 1 1 d . . . H4A H 0.9946 0.0863 0.0242 0.071 Uiso 1 1 calc R . . H4B H 0.9914 0.1811 0.0578 0.071 Uiso 1 1 calc R . . C5 C 0.9420(3) 0.2397(2) -0.00066(12) 0.0643(8) Uani 1 1 d . . . H5A H 0.8820 0.2125 -0.0244 0.077 Uiso 1 1 calc R . . H5B H 1.0473 0.2483 -0.0094 0.077 Uiso 1 1 calc R . . C6 C 0.8808(3) 0.3541(2) 0.01139(11) 0.0616(8) Uani 1 1 d . . . H6A H 0.9404 0.3830 0.0349 0.074 Uiso 1 1 calc R . . H6B H 0.8914 0.4058 -0.0116 0.074 Uiso 1 1 calc R . . N7 N 0.7178(3) 0.3459(2) 0.02230(8) 0.0507(5) Uani 1 1 d . . . H7 H 0.715(3) 0.291(3) 0.0371(9) 0.050(8) Uiso 1 1 d . . . C8 C 0.6434(3) 0.4361(2) 0.03931(8) 0.0436(5) Uani 1 1 d . . . C9 C 0.5269(3) 0.4184(2) 0.06783(9) 0.0518(6) Uani 1 1 d . . . C10 C 0.4465(3) 0.5032(2) 0.08461(9) 0.0527(6) Uani 1 1 d . . . C11 C 0.4770(3) 0.6150(2) 0.07610(9) 0.0558(7) Uani 1 1 d . . . C12 C 0.5893(3) 0.6325(2) 0.04694(10) 0.0557(7) Uani 1 1 d . . . C13 C 0.6695(3) 0.5474(2) 0.02914(8) 0.0479(6) Uani 1 1 d . . . C14 C 0.7823(4) 0.0580(2) 0.08375(10) 0.0602(7) Uani 1 1 d . . . H14A H 0.6764 0.0479 0.0918 0.072 Uiso 1 1 calc R . . H14B H 0.8318 0.1056 0.1045 0.072 Uiso 1 1 calc R . . C15 C 0.8610(4) -0.0560(3) 0.08532(11) 0.0685(8) Uani 1 1 d . . . H15A H 0.8316 -0.0981 0.0606 0.082 Uiso 1 1 calc R . . H15B H 0.9716 -0.0452 0.0852 0.082 Uiso 1 1 calc R . . C16 C 0.8218(4) -0.1216(3) 0.12214(11) 0.0678(8) Uani 1 1 d . . . H16A H 0.7119 -0.1357 0.1218 0.081 Uiso 1 1 calc R . . H16B H 0.8475 -0.0787 0.1469 0.081 Uiso 1 1 calc R . . N17 N 0.9050(4) -0.2291(2) 0.12349(11) 0.0697(8) Uani 1 1 d . . . H17 H 0.957(5) -0.247(3) 0.1046(14) 0.095(16) Uiso 1 1 d . . . C18 C 0.8400(3) -0.3234(3) 0.13952(9) 0.0567(7) Uani 1 1 d . . . C19 C 0.8762(3) -0.4304(3) 0.12401(9) 0.0552(7) Uani 1 1 d . . . C20 C 0.8174(3) -0.5269(3) 0.13958(9) 0.0581(7) Uani 1 1 d . . . C21 C 0.7179(4) -0.5268(3) 0.17163(11) 0.0725(9) Uani 1 1 d . . . C22 C 0.6829(4) -0.4206(4) 0.18758(11) 0.0796(10) Uani 1 1 d . . . C23 C 0.7434(4) -0.3253(3) 0.17284(10) 0.0708(9) Uani 1 1 d . . . C24 C 0.0059(5) 0.4410(3) 0.25628(14) 0.0857(11) Uani 1 1 d . . . H24 H -0.0249 0.3715 0.2662 0.103 Uiso 1 1 calc R . . C25 C -0.0394(5) 0.5357(4) 0.27579(15) 0.0993(13) Uani 1 1 d . . . H25 H -0.1025 0.5286 0.2985 0.119 Uiso 1 1 calc R . . N26 N 0.0015(4) 0.6375(3) 0.26424(12) 0.0907(10) Uani 1 1 d . . . C27 C 0.0873(5) 0.6423(3) 0.23262(14) 0.0848(11) Uani 1 1 d . . . H27 H 0.1156 0.7132 0.2235 0.102 Uiso 1 1 calc R . . C28 C 0.1421(5) 0.5509(3) 0.21057(12) 0.0786(10) Uani 1 1 d . . . H28 H 0.2081 0.5610 0.1886 0.094 Uiso 1 1 calc R . . C29 C 0.0968(4) 0.4467(3) 0.22198(10) 0.0607(7) Uani 1 1 d . . . C30 C 0.1479(4) 0.3485(4) 0.19672(12) 0.0792(10) Uani 1 1 d . . . H30 H 0.2177 0.3626 0.1759 0.095 Uiso 1 1 calc R . . C31 C 0.1054(4) 0.2505(3) 0.20114(13) 0.0783(10) Uani 1 1 d . . . H31 H 0.0338 0.2369 0.2215 0.094 Uiso 1 1 calc R . . C32 C 0.1587(4) 0.1514(3) 0.17667(11) 0.0666(9) Uani 1 1 d . . . C33 C 0.2454(5) 0.1555(3) 0.14150(13) 0.0852(11) Uani 1 1 d . . . H33 H 0.2754 0.2235 0.1301 0.102 Uiso 1 1 calc R . . C34 C 0.2856(4) 0.0554(3) 0.12390(11) 0.0785(10) Uani 1 1 d . . . H34 H 0.3458 0.0566 0.1004 0.094 Uiso 1 1 calc R . . N35 N 0.2429(4) -0.0424(3) 0.13869(11) 0.0807(8) Uani 1 1 d . . . C36 C 0.1649(5) -0.0440(3) 0.17177(13) 0.0799(10) Uani 1 1 d . . . H36 H 0.1372 -0.1130 0.1827 0.096 Uiso 1 1 calc R . . C37 C 0.1209(4) 0.0502(4) 0.19160(11) 0.0814(11) Uani 1 1 d . . . H37 H 0.0643 0.0449 0.2156 0.098 Uiso 1 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 0.06277(14) 0.05796(14) 0.08638(18) -0.01395(10) 0.00051(11) 0.01305(9) I2 0.08752(18) 0.0907(2) 0.0949(2) 0.04123(14) -0.00993(14) -0.02627(13) F1 0.0905(12) 0.0332(8) 0.0835(12) 0.0103(8) 0.0322(10) 0.0022(8) F2 0.0833(12) 0.0835(13) 0.0833(13) 0.0075(10) 0.0515(11) 0.0106(10) F3 0.0780(13) 0.0383(9) 0.1215(17) 0.0044(9) 0.0203(11) -0.0104(8) F4 0.0676(10) 0.0499(10) 0.0905(12) 0.0086(9) 0.0249(9) -0.0117(8) F5 0.0827(11) 0.0627(10) 0.0509(9) 0.0006(8) 0.0217(8) -0.0109(8) F6 0.0924(14) 0.0584(11) 0.0929(14) 0.0057(10) -0.0066(11) 0.0086(10) F7 0.142(2) 0.122(2) 0.0888(15) 0.0155(15) 0.0648(15) 0.0005(16) F8 0.148(2) 0.0782(15) 0.0864(15) -0.0116(12) 0.0417(15) 0.0038(14) C1 0.0414(12) 0.0356(13) 0.0631(16) -0.0062(11) 0.0113(11) 0.0022(9) C2 0.0392(12) 0.0490(15) 0.0593(16) -0.0106(12) 0.0122(11) -0.0052(10) N3 0.0372(10) 0.0438(12) 0.0569(13) -0.0053(10) 0.0084(9) -0.0037(8) C4 0.0395(13) 0.0493(16) 0.090(2) -0.0062(15) 0.0045(13) -0.0058(11) C5 0.0492(15) 0.0494(17) 0.096(2) -0.0114(15) 0.0268(15) -0.0116(12) C6 0.0494(14) 0.0448(15) 0.092(2) -0.0105(14) 0.0267(14) -0.0135(12) N7 0.0519(12) 0.0373(12) 0.0636(15) 0.0023(11) 0.0162(11) -0.0111(9) C8 0.0396(12) 0.0372(12) 0.0537(15) -0.0037(10) -0.0027(10) -0.0063(9) C9 0.0508(14) 0.0462(15) 0.0587(16) 0.0025(12) 0.0060(12) -0.0077(11) C10 0.0505(14) 0.0544(16) 0.0539(16) 0.0017(13) 0.0153(12) 0.0045(12) C11 0.0516(14) 0.0458(15) 0.0693(18) -0.0048(13) -0.0111(13) 0.0043(11) C12 0.0576(15) 0.0343(13) 0.0747(19) -0.0007(13) -0.0086(14) -0.0059(11) C13 0.0444(13) 0.0474(14) 0.0521(15) -0.0012(11) 0.0041(11) -0.0180(11) C14 0.0618(17) 0.0462(16) 0.072(2) -0.0135(14) 0.0009(14) 0.0014(12) C15 0.0697(19) 0.0571(19) 0.079(2) 0.0004(16) 0.0004(16) 0.0069(14) C16 0.0618(17) 0.0570(19) 0.085(2) -0.0032(17) 0.0049(16) -0.0053(14) N17 0.0685(17) 0.0546(17) 0.087(2) 0.0122(15) 0.0150(16) 0.0022(13) C18 0.0582(15) 0.0609(18) 0.0507(16) 0.0002(13) -0.0030(13) -0.0029(13) C19 0.0507(14) 0.0591(18) 0.0555(17) 0.0044(14) -0.0047(12) 0.0027(12) C20 0.0589(16) 0.0625(19) 0.0526(17) 0.0091(14) -0.0067(13) 0.0027(13) C21 0.086(2) 0.063(2) 0.068(2) 0.0170(17) -0.0136(18) -0.0113(17) C22 0.084(2) 0.099(3) 0.057(2) 0.0187(19) 0.0160(17) -0.004(2) C23 0.091(2) 0.067(2) 0.0552(18) -0.0084(16) 0.0095(17) -0.0012(17) C24 0.092(3) 0.055(2) 0.110(3) -0.001(2) 0.005(2) -0.0023(18) C25 0.103(3) 0.098(3) 0.098(3) -0.018(3) 0.018(2) -0.014(3) N26 0.093(2) 0.085(2) 0.093(2) -0.0293(19) -0.0067(19) 0.0217(19) C27 0.102(3) 0.054(2) 0.097(3) 0.002(2) -0.021(2) 0.0093(19) C28 0.090(2) 0.083(3) 0.062(2) 0.0016(18) 0.0049(18) 0.003(2) C29 0.0661(18) 0.0546(18) 0.0612(19) -0.0082(14) -0.0019(15) 0.0055(14) C30 0.067(2) 0.092(3) 0.078(3) -0.006(2) 0.0025(18) 0.0001(19) C31 0.075(2) 0.081(3) 0.079(3) 0.0029(19) 0.0010(19) -0.0044(18) C32 0.0678(18) 0.062(2) 0.069(2) -0.0269(16) -0.0046(16) 0.0158(15) C33 0.095(3) 0.073(2) 0.088(3) -0.002(2) 0.013(2) -0.015(2) C34 0.083(2) 0.088(3) 0.067(2) -0.0227(19) 0.0379(18) -0.0014(19) N35 0.0807(19) 0.0668(19) 0.095(2) -0.0255(17) 0.0027(17) 0.0103(15) C36 0.089(2) 0.063(2) 0.088(3) -0.0017(19) 0.001(2) 0.0017(18) C37 0.074(2) 0.105(3) 0.066(2) -0.010(2) 0.0131(17) 0.000(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 C11 2.080(3) . ? I2 C21 2.078(3) . ? F1 C9 1.370(3) . ? F2 C10 1.355(3) . ? F3 C12 1.339(3) . ? F4 C13 1.345(3) . ? F5 C19 1.412(3) . ? F6 C20 1.352(4) . ? F7 C22 1.332(4) . ? F8 C23 1.336(4) . ? C1 C1 1.484(5) 3_655 ? C1 C2 1.518(3) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 N3 1.453(3) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? N3 C14 1.450(4) . ? N3 C4 1.481(3) . ? C4 C5 1.515(5) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.520(4) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 N7 1.472(3) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? N7 C8 1.377(3) . ? N7 H7 0.82(3) . ? C8 C13 1.387(3) . ? C8 C9 1.401(4) . ? C9 C10 1.350(4) . ? C10 C11 1.389(4) . ? C11 C12 1.388(4) . ? C12 C13 1.366(4) . ? C14 C15 1.523(4) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.468(5) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 N17 1.473(4) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? N17 C18 1.366(4) . ? N17 H17 0.80(5) . ? C18 C23 1.380(4) . ? C18 C19 1.409(4) . ? C19 C20 1.360(4) . ? C20 C21 1.364(5) . ? C21 C22 1.403(5) . ? C22 C23 1.345(5) . ? C24 C25 1.356(6) . ? C24 C29 1.377(5) . ? C24 H24 0.9300 . ? C25 N26 1.322(6) . ? C25 H25 0.9300 . ? N26 C27 1.279(5) . ? C27 C28 1.392(5) . ? C27 H27 0.9300 . ? C28 C29 1.358(5) . ? C28 H28 0.9300 . ? C29 C30 1.501(5) . ? C30 C31 1.236(5) . ? C30 H30 0.9300 . ? C31 C32 1.500(5) . ? C31 H31 0.9300 . ? C32 C37 1.344(5) . ? C32 C33 1.377(5) . ? C33 C34 1.372(5) . ? C33 H33 0.9300 . ? C34 N35 1.318(5) . ? C34 H34 0.9300 . ? N35 C36 1.278(5) . ? C36 C37 1.353(5) . ? C36 H36 0.9300 . ? C37 H37 0.9300 . ? 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 C1 C2 112.4(3) 3_655 . ? C1 C1 H1A 109.1 3_655 . ? C2 C1 H1A 109.1 . . ? C1 C1 H1B 109.1 3_655 . ? C2 C1 H1B 109.1 . . ? H1A C1 H1B 107.8 . . ? N3 C2 C1 114.8(2) . . ? N3 C2 H2A 108.6 . . ? C1 C2 H2A 108.6 . . ? N3 C2 H2B 108.6 . . ? C1 C2 H2B 108.6 . . ? H2A C2 H2B 107.5 . . ? C14 N3 C2 113.3(2) . . ? C14 N3 C4 111.3(2) . . ? C2 N3 C4 111.4(2) . . ? N3 C4 C5 113.8(2) . . ? N3 C4 H4A 108.8 . . ? C5 C4 H4A 108.8 . . ? N3 C4 H4B 108.8 . . ? C5 C4 H4B 108.8 . . ? H4A C4 H4B 107.7 . . ? C4 C5 C6 115.1(3) . . ? C4 C5 H5A 108.5 . . ? C6 C5 H5A 108.5 . . ? C4 C5 H5B 108.5 . . ? C6 C5 H5B 108.5 . . ? H5A C5 H5B 107.5 . . ? N7 C6 C5 110.2(2) . . ? N7 C6 H6A 109.6 . . ? C5 C6 H6A 109.6 . . ? N7 C6 H6B 109.6 . . ? C5 C6 H6B 109.6 . . ? H6A C6 H6B 108.1 . . ? C8 N7 C6 120.5(2) . . ? C8 N7 H7 112(2) . . ? C6 N7 H7 104(2) . . ? N7 C8 C13 125.0(2) . . ? N7 C8 C9 119.8(2) . . ? C13 C8 C9 115.1(2) . . ? C10 C9 F1 117.5(2) . . ? C10 C9 C8 122.6(3) . . ? F1 C9 C8 119.8(2) . . ? C9 C10 F2 119.4(3) . . ? C9 C10 C11 122.5(3) . . ? F2 C10 C11 118.0(2) . . ? C12 C11 C10 114.8(2) . . ? C12 C11 I1 120.9(2) . . ? C10 C11 I1 124.3(2) . . ? F3 C12 C13 117.0(3) . . ? F3 C12 C11 119.8(3) . . ? C13 C12 C11 123.2(2) . . ? F4 C13 C12 118.2(2) . . ? F4 C13 C8 120.1(2) . . ? C12 C13 C8 121.6(2) . . ? N3 C14 C15 117.2(3) . . ? N3 C14 H14A 108.0 . . ? C15 C14 H14A 108.0 . . ? N3 C14 H14B 108.0 . . ? C15 C14 H14B 108.0 . . ? H14A C14 H14B 107.2 . . ? C16 C15 C14 112.9(3) . . ? C16 C15 H15A 109.0 . . ? C14 C15 H15A 109.0 . . ? C16 C15 H15B 109.0 . . ? C14 C15 H15B 109.0 . . ? H15A C15 H15B 107.8 . . ? C15 C16 N17 111.4(3) . . ? C15 C16 H16A 109.4 . . ? N17 C16 H16A 109.4 . . ? C15 C16 H16B 109.4 . . ? N17 C16 H16B 109.4 . . ? H16A C16 H16B 108.0 . . ? C18 N17 C16 121.4(3) . . ? C18 N17 H17 109(3) . . ? C16 N17 H17 120(3) . . ? N17 C18 C23 125.0(3) . . ? N17 C18 C19 120.9(3) . . ? C23 C18 C19 114.0(3) . . ? C20 C19 C18 123.1(3) . . ? C20 C19 F5 117.9(3) . . ? C18 C19 F5 118.9(3) . . ? F6 C20 C19 118.3(3) . . ? F6 C20 C21 119.7(3) . . ? C19 C20 C21 122.0(3) . . ? C20 C21 C22 115.2(3) . . ? C20 C21 I2 123.8(3) . . ? C22 C21 I2 120.9(3) . . ? F7 C22 C23 117.8(4) . . ? F7 C22 C21 119.3(3) . . ? C23 C22 C21 122.9(3) . . ? F8 C23 C22 118.4(3) . . ? F8 C23 C18 118.9(3) . . ? C22 C23 C18 122.7(3) . . ? C25 C24 C29 120.7(4) . . ? C25 C24 H24 119.7 . . ? C29 C24 H24 119.7 . . ? N26 C25 C24 123.5(4) . . ? N26 C25 H25 118.2 . . ? C24 C25 H25 118.2 . . ? C27 N26 C25 115.5(4) . . ? N26 C27 C28 125.9(4) . . ? N26 C27 H27 117.1 . . ? C28 C27 H27 117.1 . . ? C29 C28 C27 118.3(4) . . ? C29 C28 H28 120.9 . . ? C27 C28 H28 120.9 . . ? C28 C29 C24 116.0(3) . . ? C28 C29 C30 118.5(3) . . ? C24 C29 C30 125.5(3) . . ? C31 C30 C29 125.7(4) . . ? C31 C30 H30 117.2 . . ? C29 C30 H30 117.2 . . ? C30 C31 C32 126.0(4) . . ? C30 C31 H31 117.0 . . ? C32 C31 H31 117.0 . . ? C37 C32 C33 118.1(3) . . ? C37 C32 C31 116.0(3) . . ? C33 C32 C31 125.9(4) . . ? C34 C33 C32 117.4(3) . . ? C34 C33 H33 121.3 . . ? C32 C33 H33 121.3 . . ? N35 C34 C33 123.0(3) . . ? N35 C34 H34 118.5 . . ? C33 C34 H34 118.5 . . ? C36 N35 C34 118.3(3) . . ? N35 C36 C37 123.0(4) . . ? N35 C36 H36 118.5 . . ? C37 C36 H36 118.5 . . ? C32 C37 C36 120.2(3) . . ? C32 C37 H37 119.9 . . ? C36 C37 H37 119.9 . . ? 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 C1 C1 C2 N3 172.9(3) 3_655 . . . ? C1 C2 N3 C14 58.0(3) . . . . ? C1 C2 N3 C4 -175.5(2) . . . . ? C14 N3 C4 C5 -164.4(2) . . . . ? C2 N3 C4 C5 68.1(3) . . . . ? N3 C4 C5 C6 67.7(3) . . . . ? C4 C5 C6 N7 -61.8(4) . . . . ? C5 C6 N7 C8 171.6(3) . . . . ? C6 N7 C8 C13 35.5(4) . . . . ? C6 N7 C8 C9 -147.6(3) . . . . ? N7 C8 C9 C10 -177.9(3) . . . . ? C13 C8 C9 C10 -0.6(4) . . . . ? N7 C8 C9 F1 0.5(4) . . . . ? C13 C8 C9 F1 177.7(2) . . . . ? F1 C9 C10 F2 3.0(4) . . . . ? C8 C9 C10 F2 -178.6(2) . . . . ? F1 C9 C10 C11 179.1(3) . . . . ? C8 C9 C10 C11 -2.5(4) . . . . ? C9 C10 C11 C12 4.1(4) . . . . ? F2 C10 C11 C12 -179.7(2) . . . . ? C9 C10 C11 I1 -175.6(2) . . . . ? F2 C10 C11 I1 0.6(4) . . . . ? C10 C11 C12 F3 178.2(3) . . . . ? I1 C11 C12 F3 -2.1(4) . . . . ? C10 C11 C12 C13 -2.9(4) . . . . ? I1 C11 C12 C13 176.9(2) . . . . ? F3 C12 C13 F4 -3.6(4) . . . . ? C11 C12 C13 F4 177.4(2) . . . . ? F3 C12 C13 C8 178.9(2) . . . . ? C11 C12 C13 C8 0.0(4) . . . . ? N7 C8 C13 F4 1.5(4) . . . . ? C9 C8 C13 F4 -175.6(2) . . . . ? N7 C8 C13 C12 179.0(3) . . . . ? C9 C8 C13 C12 1.9(4) . . . . ? C2 N3 C14 C15 59.8(3) . . . . ? C4 N3 C14 C15 -66.8(3) . . . . ? N3 C14 C15 C16 -164.9(3) . . . . ? C14 C15 C16 N17 -177.6(3) . . . . ? C15 C16 N17 C18 -146.3(3) . . . . ? C16 N17 C18 C23 -35.5(5) . . . . ? C16 N17 C18 C19 148.6(3) . . . . ? N17 C18 C19 C20 178.4(3) . . . . ? C23 C18 C19 C20 2.0(4) . . . . ? N17 C18 C19 F5 1.6(4) . . . . ? C23 C18 C19 F5 -174.7(3) . . . . ? C18 C19 C20 F6 178.7(3) . . . . ? F5 C19 C20 F6 -4.5(4) . . . . ? C18 C19 C20 C21 0.1(5) . . . . ? F5 C19 C20 C21 176.9(3) . . . . ? F6 C20 C21 C22 -179.5(3) . . . . ? C19 C20 C21 C22 -0.9(5) . . . . ? F6 C20 C21 I2 2.0(4) . . . . ? C19 C20 C21 I2 -179.4(2) . . . . ? C20 C21 C22 F7 -179.2(3) . . . . ? I2 C21 C22 F7 -0.6(5) . . . . ? C20 C21 C22 C23 -0.6(5) . . . . ? I2 C21 C22 C23 178.0(3) . . . . ? F7 C22 C23 F8 2.5(5) . . . . ? C21 C22 C23 F8 -176.1(3) . . . . ? F7 C22 C23 C18 -178.4(3) . . . . ? C21 C22 C23 C18 3.0(6) . . . . ? N17 C18 C23 F8 -0.6(5) . . . . ? C19 C18 C23 F8 175.6(3) . . . . ? N17 C18 C23 C22 -179.7(3) . . . . ? C19 C18 C23 C22 -3.5(5) . . . . ? C29 C24 C25 N26 -1.3(7) . . . . ? C24 C25 N26 C27 0.5(7) . . . . ? C25 N26 C27 C28 -1.4(6) . . . . ? N26 C27 C28 C29 3.0(6) . . . . ? C27 C28 C29 C24 -3.4(5) . . . . ? C27 C28 C29 C30 176.4(3) . . . . ? C25 C24 C29 C28 2.7(6) . . . . ? C25 C24 C29 C30 -177.0(4) . . . . ? C28 C29 C30 C31 -173.5(4) . . . . ? C24 C29 C30 C31 6.3(6) . . . . ? C29 C30 C31 C32 -178.5(3) . . . . ? C30 C31 C32 C37 167.7(4) . . . . ? C30 C31 C32 C33 -10.2(7) . . . . ? C37 C32 C33 C34 0.7(5) . . . . ? C31 C32 C33 C34 178.7(4) . . . . ? C32 C33 C34 N35 1.2(6) . . . . ? C33 C34 N35 C36 -2.5(6) . . . . ? C34 N35 C36 C37 1.8(6) . . . . ? C33 C32 C37 C36 -1.4(5) . . . . ? C31 C32 C37 C36 -179.5(3) . . . . ? N35 C36 C37 C32 0.1(6) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 29.04 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.730 _refine_diff_density_min -0.715 _refine_diff_density_rms 0.075