# Electronic Supplementary Material (ESI) for Chemical Communications # 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_publication_text data_shelxl #TrackingRef 'p2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C54 H42 F10 N4' _chemical_formula_weight 936.92 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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.7122(4) _cell_length_b 10.8416(5) _cell_length_c 11.2497(5) _cell_angle_alpha 103.975(2) _cell_angle_beta 94.023(2) _cell_angle_gamma 103.426(2) _cell_volume 1222.11(9) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3809 _cell_measurement_theta_min 2.7 _cell_measurement_theta_max 21.2 _exptl_crystal_description block _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.273 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 484 _exptl_absorpt_coefficient_mu 0.102 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.952 _exptl_absorpt_correction_T_max 0.972 _exptl_absorpt_process_details 'SADABS (Bruker, 1999)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 axs kappa apex2 CCD Diffractometer' _diffrn_measurement_method '\w and \f scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 14183 _diffrn_reflns_av_R_equivalents 0.0336 _diffrn_reflns_av_sigmaI/netI 0.0281 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 21.88 _reflns_number_total 2916 _reflns_number_gt 2187 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2004)' _computing_cell_refinement 'APEX2/SAINT (Bruker, 2004)' _computing_data_reduction 'SAINT/XPREP (Bruker, 2004)' _computing_structure_solution 'SIR92 (Altornare et al., 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0556P)^2^+0.4283P] 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 SHELXL _refine_ls_extinction_coef 0.0087(18) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2916 _refine_ls_number_parameters 316 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0609 _refine_ls_R_factor_gt 0.0398 _refine_ls_wR_factor_ref 0.1192 _refine_ls_wR_factor_gt 0.1000 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.0437(3) 0.0081(3) 0.1824(3) 0.0638(8) Uani 1 1 d . . . C2 C -0.0613(3) -0.0917(3) 0.1835(4) 0.0824(10) Uani 1 1 d . . . C3 C -0.1292(3) -0.0803(3) 0.2813(4) 0.0775(10) Uani 1 1 d . . . C4 C -0.0927(3) 0.0287(3) 0.3772(3) 0.0644(8) Uani 1 1 d . . . C5 C 0.0122(3) 0.1276(3) 0.3740(3) 0.0537(7) Uani 1 1 d . . . C6 C 0.0828(2) 0.1212(3) 0.2767(2) 0.0462(7) Uani 1 1 d . . . C7 C 0.1942(2) 0.2315(2) 0.2729(2) 0.0423(6) Uani 1 1 d . . . C8 C 0.1691(2) 0.3331(3) 0.2318(2) 0.0436(7) Uani 1 1 d . . . C9 C 0.0469(3) 0.3510(3) 0.1884(2) 0.0559(8) Uani 1 1 d . . . H9 H -0.0342 0.2935 0.1813 0.067 Uiso 1 1 calc R . . C10 C 0.0725(3) 0.4661(3) 0.1603(3) 0.0611(8) Uani 1 1 d . . . H10 H 0.0125 0.5040 0.1293 0.073 Uiso 1 1 calc R . . C11 C 0.2110(3) 0.5207(3) 0.1869(2) 0.0473(7) Uani 1 1 d . . . C12 C 0.2851(3) 0.6514(3) 0.1714(2) 0.0557(8) Uani 1 1 d . . . C13 C 0.2150(4) 0.7552(3) 0.2308(3) 0.1004(14) Uani 1 1 d . . . H13A H 0.1313 0.7374 0.1840 0.151 Uiso 1 1 calc R . . H13B H 0.2652 0.8411 0.2312 0.151 Uiso 1 1 calc R . . H13C H 0.2048 0.7517 0.3141 0.151 Uiso 1 1 calc R . . C14 C 0.4245(3) 0.6876(3) 0.2351(3) 0.0907(12) Uani 1 1 d . . . H14A H 0.4241 0.6925 0.3215 0.136 Uiso 1 1 calc R . . H14B H 0.4701 0.7713 0.2256 0.136 Uiso 1 1 calc R . . H14C H 0.4669 0.6217 0.1983 0.136 Uiso 1 1 calc R . . C15 C 0.2893(2) 0.6439(2) 0.0349(2) 0.0430(6) Uani 1 1 d . . . C16 C 0.2768(3) 0.5270(3) -0.0518(2) 0.0540(7) Uani 1 1 d . . . H16 H 0.2600 0.4494 -0.0273 0.065 Uiso 1 1 calc R . . C17 C 0.2884(3) 0.5212(3) -0.1743(2) 0.0550(7) Uani 1 1 d . . . H17 H 0.2782 0.4398 -0.2303 0.066 Uiso 1 1 calc R . . C18 C 0.3146(2) 0.6323(3) -0.2155(2) 0.0443(7) Uani 1 1 d . . . C19 C 0.3278(3) 0.7497(3) -0.1283(3) 0.0590(8) Uani 1 1 d . . . H19 H 0.3465 0.8275 -0.1525 0.071 Uiso 1 1 calc R . . C20 C 0.3142(3) 0.7553(3) -0.0068(2) 0.0585(8) Uani 1 1 d . . . H20 H 0.3221 0.8365 0.0487 0.070 Uiso 1 1 calc R . . C21 C 0.3313(2) 0.6314(3) -0.3499(2) 0.0520(7) Uani 1 1 d . . . C22 C 0.3225(3) 0.4938(3) -0.4315(3) 0.0762(10) Uani 1 1 d . . . H22A H 0.3369 0.4989 -0.5136 0.114 Uiso 1 1 calc R . . H22B H 0.2381 0.4377 -0.4340 0.114 Uiso 1 1 calc R . . H22C H 0.3870 0.4585 -0.3980 0.114 Uiso 1 1 calc R . . C23 C 0.2269(3) 0.6859(4) -0.4033(3) 0.0872(12) Uani 1 1 d . . . H23A H 0.2345 0.7740 -0.3549 0.131 Uiso 1 1 calc R . . H23B H 0.1428 0.6315 -0.4013 0.131 Uiso 1 1 calc R . . H23C H 0.2378 0.6863 -0.4872 0.131 Uiso 1 1 calc R . . C24 C 0.4638(2) 0.7178(3) -0.3499(2) 0.0468(7) Uani 1 1 d . . . C25 C 0.5061(3) 0.8298(3) -0.3882(2) 0.0577(8) Uani 1 1 d . . . H25 H 0.4539 0.8727 -0.4235 0.069 Uiso 1 1 calc R . . C26 C 0.6403(3) 0.8676(3) -0.3651(2) 0.0556(7) Uani 1 1 d . . . H26 H 0.6938 0.9404 -0.3821 0.067 Uiso 1 1 calc R . . C27 C 0.6807(2) 0.7783(2) -0.3124(2) 0.0422(6) Uani 1 1 d . . . N1 N 0.26804(19) 0.4427(2) 0.22869(18) 0.0446(6) Uani 1 1 d . . . N2 N 0.56980(19) 0.6885(2) -0.30481(19) 0.0439(6) Uani 1 1 d . . . F1 F 0.10971(19) -0.00620(18) 0.08556(18) 0.0954(7) Uani 1 1 d . . . F2 F -0.0961(2) -0.2001(2) 0.0892(2) 0.1396(10) Uani 1 1 d . . . F3 F -0.2319(2) -0.17691(19) 0.2835(2) 0.1261(9) Uani 1 1 d . . . F4 F -0.15859(18) 0.0404(2) 0.47474(19) 0.1001(7) Uani 1 1 d . . . F5 F 0.04537(17) 0.23361(18) 0.47139(15) 0.0814(6) Uani 1 1 d . . . H2 H 0.572(2) 0.624(2) -0.277(2) 0.037(7) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.061(2) 0.0515(19) 0.070(2) 0.0089(17) 0.0170(16) 0.0031(16) C2 0.071(2) 0.044(2) 0.108(3) -0.001(2) 0.006(2) -0.0088(18) C3 0.052(2) 0.052(2) 0.124(3) 0.033(2) 0.017(2) -0.0082(17) C4 0.0501(19) 0.067(2) 0.087(2) 0.043(2) 0.0286(17) 0.0083(17) C5 0.0494(18) 0.0510(18) 0.0587(19) 0.0200(16) 0.0084(15) 0.0030(15) C6 0.0387(16) 0.0476(17) 0.0525(17) 0.0187(14) 0.0086(13) 0.0051(13) C7 0.0364(16) 0.0476(16) 0.0406(15) 0.0134(12) 0.0100(11) 0.0033(12) C8 0.0370(16) 0.0543(17) 0.0404(15) 0.0182(13) 0.0095(11) 0.0063(13) C9 0.0381(17) 0.075(2) 0.0580(18) 0.0273(16) 0.0100(13) 0.0090(14) C10 0.051(2) 0.083(2) 0.0645(19) 0.0365(17) 0.0135(14) 0.0277(16) C11 0.0544(19) 0.0561(17) 0.0364(14) 0.0182(13) 0.0119(12) 0.0156(14) C12 0.078(2) 0.0486(17) 0.0424(16) 0.0171(13) 0.0098(14) 0.0138(15) C13 0.187(4) 0.069(2) 0.069(2) 0.0268(18) 0.063(2) 0.056(3) C14 0.105(3) 0.074(2) 0.069(2) 0.0362(18) -0.027(2) -0.030(2) C15 0.0437(16) 0.0464(16) 0.0419(15) 0.0172(13) 0.0088(12) 0.0110(12) C16 0.071(2) 0.0442(17) 0.0497(18) 0.0208(14) 0.0153(14) 0.0090(14) C17 0.0637(19) 0.0484(17) 0.0476(17) 0.0084(14) 0.0139(13) 0.0068(14) C18 0.0307(15) 0.0585(18) 0.0452(16) 0.0189(14) 0.0055(11) 0.0088(12) C19 0.080(2) 0.0528(19) 0.0554(19) 0.0304(16) 0.0208(15) 0.0189(15) C20 0.086(2) 0.0441(17) 0.0489(18) 0.0148(14) 0.0193(15) 0.0180(15) C21 0.0374(16) 0.078(2) 0.0422(16) 0.0235(15) 0.0063(12) 0.0101(14) C22 0.063(2) 0.095(3) 0.0479(18) 0.0063(17) 0.0103(14) -0.0123(17) C23 0.0459(19) 0.161(4) 0.072(2) 0.063(2) 0.0072(16) 0.026(2) C24 0.0423(17) 0.0650(18) 0.0385(15) 0.0223(14) 0.0085(12) 0.0146(14) C25 0.053(2) 0.073(2) 0.0608(18) 0.0363(16) 0.0119(14) 0.0231(15) C26 0.057(2) 0.0512(17) 0.0654(19) 0.0289(15) 0.0165(14) 0.0097(14) C27 0.0407(17) 0.0432(16) 0.0444(15) 0.0179(12) 0.0133(12) 0.0052(13) N1 0.0422(13) 0.0490(13) 0.0441(12) 0.0202(11) 0.0074(10) 0.0060(11) N2 0.0389(14) 0.0497(14) 0.0487(13) 0.0261(12) 0.0095(10) 0.0075(12) F1 0.0930(14) 0.0847(14) 0.0844(13) -0.0087(11) 0.0326(11) 0.0025(11) F2 0.125(2) 0.0712(15) 0.166(2) -0.0260(15) 0.0223(16) -0.0253(13) F3 0.0820(15) 0.0760(14) 0.207(3) 0.0507(15) 0.0329(15) -0.0233(12) F4 0.0821(14) 0.1146(16) 0.1198(16) 0.0638(14) 0.0541(12) 0.0104(12) F5 0.0773(13) 0.0859(13) 0.0643(11) 0.0100(10) 0.0261(9) -0.0061(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 F1 1.337(3) . ? C1 C6 1.369(4) . ? C1 C2 1.371(4) . ? C2 F2 1.335(4) . ? C2 C3 1.358(5) . ? C3 F3 1.338(3) . ? C3 C4 1.350(4) . ? C4 F4 1.343(3) . ? C4 C5 1.370(4) . ? C5 F5 1.340(3) . ? C5 C6 1.371(4) . ? C6 C7 1.491(3) . ? C7 C8 1.365(3) . ? C7 C27 1.418(3) 2_665 ? C8 N1 1.406(3) . ? C8 C9 1.436(3) . ? C9 C10 1.332(4) . ? C9 H9 0.9300 . ? C10 C11 1.444(4) . ? C10 H10 0.9300 . ? C11 N1 1.305(3) . ? C11 C12 1.511(4) . ? C12 C15 1.523(3) . ? C12 C14 1.530(4) . ? C12 C13 1.542(4) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 C16 1.371(3) . ? C15 C20 1.376(3) . ? C16 C17 1.381(3) . ? C16 H16 0.9300 . ? C17 C18 1.369(3) . ? C17 H17 0.9300 . ? C18 C19 1.377(4) . ? C18 C21 1.533(3) . ? C19 C20 1.373(4) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? C21 C24 1.509(4) . ? C21 C22 1.529(4) . ? C21 C23 1.532(4) . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 N2 1.346(3) . ? C24 C25 1.375(3) . ? C25 C26 1.387(4) . ? C25 H25 0.9300 . ? C26 C27 1.384(3) . ? C26 H26 0.9300 . ? C27 N2 1.372(3) . ? C27 C7 1.418(3) 2_665 ? N2 H2 0.84(2) . ? 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 F1 C1 C6 119.2(2) . . ? F1 C1 C2 118.5(3) . . ? C6 C1 C2 122.3(3) . . ? F2 C2 C3 120.1(3) . . ? F2 C2 C1 120.2(3) . . ? C3 C2 C1 119.7(3) . . ? F3 C3 C4 119.7(3) . . ? F3 C3 C2 120.3(3) . . ? C4 C3 C2 120.0(3) . . ? F4 C4 C3 120.4(3) . . ? F4 C4 C5 120.2(3) . . ? C3 C4 C5 119.4(3) . . ? F5 C5 C4 117.4(3) . . ? F5 C5 C6 119.9(2) . . ? C4 C5 C6 122.7(3) . . ? C1 C6 C5 115.9(2) . . ? C1 C6 C7 122.0(2) . . ? C5 C6 C7 122.1(2) . . ? C8 C7 C27 125.0(2) . 2_665 ? C8 C7 C6 118.4(2) . . ? C27 C7 C6 116.6(2) 2_665 . ? C7 C8 N1 122.0(2) . . ? C7 C8 C9 129.1(2) . . ? N1 C8 C9 108.8(2) . . ? C10 C9 C8 106.6(2) . . ? C10 C9 H9 126.7 . . ? C8 C9 H9 126.7 . . ? C9 C10 C11 107.1(2) . . ? C9 C10 H10 126.4 . . ? C11 C10 H10 126.4 . . ? N1 C11 C10 111.3(2) . . ? N1 C11 C12 122.3(2) . . ? C10 C11 C12 126.3(2) . . ? C11 C12 C15 110.3(2) . . ? C11 C12 C14 110.3(2) . . ? C15 C12 C14 108.1(2) . . ? C11 C12 C13 107.3(2) . . ? C15 C12 C13 110.7(2) . . ? C14 C12 C13 110.2(3) . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C12 C14 H14A 109.5 . . ? C12 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C12 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C16 C15 C20 116.4(2) . . ? C16 C15 C12 121.9(2) . . ? C20 C15 C12 121.5(2) . . ? C15 C16 C17 121.9(2) . . ? C15 C16 H16 119.1 . . ? C17 C16 H16 119.1 . . ? C18 C17 C16 121.7(3) . . ? C18 C17 H17 119.2 . . ? C16 C17 H17 119.2 . . ? C17 C18 C19 116.4(2) . . ? C17 C18 C21 123.6(2) . . ? C19 C18 C21 119.9(2) . . ? C20 C19 C18 121.9(2) . . ? C20 C19 H19 119.0 . . ? C18 C19 H19 119.0 . . ? C19 C20 C15 121.7(3) . . ? C19 C20 H20 119.2 . . ? C15 C20 H20 119.2 . . ? C24 C21 C22 108.2(2) . . ? C24 C21 C23 110.0(2) . . ? C22 C21 C23 108.9(2) . . ? C24 C21 C18 107.7(2) . . ? C22 C21 C18 112.7(2) . . ? C23 C21 C18 109.4(2) . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C21 C23 H23A 109.5 . . ? C21 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C21 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? N2 C24 C25 107.0(2) . . ? N2 C24 C21 119.7(2) . . ? C25 C24 C21 133.3(2) . . ? C24 C25 C26 108.0(2) . . ? C24 C25 H25 126.0 . . ? C26 C25 H25 126.0 . . ? C27 C26 C25 108.1(2) . . ? C27 C26 H26 126.0 . . ? C25 C26 H26 126.0 . . ? N2 C27 C26 105.8(2) . . ? N2 C27 C7 122.4(2) . 2_665 ? C26 C27 C7 131.8(2) . 2_665 ? C11 N1 C8 106.1(2) . . ? C24 N2 C27 111.1(2) . . ? C24 N2 H2 126.8(16) . . ? C27 N2 H2 122.1(16) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag F1 C1 C2 F2 -0.2(5) . . . . ? C6 C1 C2 F2 179.7(3) . . . . ? F1 C1 C2 C3 179.3(3) . . . . ? C6 C1 C2 C3 -0.7(5) . . . . ? F2 C2 C3 F3 -0.5(5) . . . . ? C1 C2 C3 F3 180.0(3) . . . . ? F2 C2 C3 C4 179.2(3) . . . . ? C1 C2 C3 C4 -0.4(5) . . . . ? F3 C3 C4 F4 0.2(5) . . . . ? C2 C3 C4 F4 -179.5(3) . . . . ? F3 C3 C4 C5 -179.7(3) . . . . ? C2 C3 C4 C5 0.7(5) . . . . ? F4 C4 C5 F5 0.5(4) . . . . ? C3 C4 C5 F5 -179.7(3) . . . . ? F4 C4 C5 C6 -179.8(2) . . . . ? C3 C4 C5 C6 0.1(4) . . . . ? F1 C1 C6 C5 -178.6(3) . . . . ? C2 C1 C6 C5 1.4(4) . . . . ? F1 C1 C6 C7 2.3(4) . . . . ? C2 C1 C6 C7 -177.7(3) . . . . ? F5 C5 C6 C1 178.7(2) . . . . ? C4 C5 C6 C1 -1.1(4) . . . . ? F5 C5 C6 C7 -2.2(4) . . . . ? C4 C5 C6 C7 178.0(3) . . . . ? C1 C6 C7 C8 95.5(3) . . . . ? C5 C6 C7 C8 -83.6(3) . . . . ? C1 C6 C7 C27 -84.2(3) . . . 2_665 ? C5 C6 C7 C27 96.7(3) . . . 2_665 ? C27 C7 C8 N1 -2.2(4) 2_665 . . . ? C6 C7 C8 N1 178.1(2) . . . . ? C27 C7 C8 C9 179.0(2) 2_665 . . . ? C6 C7 C8 C9 -0.7(4) . . . . ? C7 C8 C9 C10 179.2(3) . . . . ? N1 C8 C9 C10 0.2(3) . . . . ? C8 C9 C10 C11 -0.4(3) . . . . ? C9 C10 C11 N1 0.4(3) . . . . ? C9 C10 C11 C12 -179.1(2) . . . . ? N1 C11 C12 C15 107.6(3) . . . . ? C10 C11 C12 C15 -73.0(3) . . . . ? N1 C11 C12 C14 -11.7(4) . . . . ? C10 C11 C12 C14 167.7(3) . . . . ? N1 C11 C12 C13 -131.8(3) . . . . ? C10 C11 C12 C13 47.7(3) . . . . ? C11 C12 C15 C16 -24.6(3) . . . . ? C14 C12 C15 C16 96.1(3) . . . . ? C13 C12 C15 C16 -143.2(3) . . . . ? C11 C12 C15 C20 159.7(2) . . . . ? C14 C12 C15 C20 -79.7(3) . . . . ? C13 C12 C15 C20 41.1(4) . . . . ? C20 C15 C16 C17 -0.1(4) . . . . ? C12 C15 C16 C17 -176.0(3) . . . . ? C15 C16 C17 C18 0.8(4) . . . . ? C16 C17 C18 C19 -0.4(4) . . . . ? C16 C17 C18 C21 178.6(2) . . . . ? C17 C18 C19 C20 -0.6(4) . . . . ? C21 C18 C19 C20 -179.7(2) . . . . ? C18 C19 C20 C15 1.4(4) . . . . ? C16 C15 C20 C19 -1.0(4) . . . . ? C12 C15 C20 C19 175.0(3) . . . . ? C17 C18 C21 C24 -122.2(3) . . . . ? C19 C18 C21 C24 56.8(3) . . . . ? C17 C18 C21 C22 -2.9(3) . . . . ? C19 C18 C21 C22 176.0(2) . . . . ? C17 C18 C21 C23 118.4(3) . . . . ? C19 C18 C21 C23 -62.7(3) . . . . ? C22 C21 C24 N2 -62.1(3) . . . . ? C23 C21 C24 N2 179.0(2) . . . . ? C18 C21 C24 N2 59.9(3) . . . . ? C22 C21 C24 C25 118.1(3) . . . . ? C23 C21 C24 C25 -0.8(4) . . . . ? C18 C21 C24 C25 -119.8(3) . . . . ? N2 C24 C25 C26 0.0(3) . . . . ? C21 C24 C25 C26 179.7(3) . . . . ? C24 C25 C26 C27 0.1(3) . . . . ? C25 C26 C27 N2 0.0(3) . . . . ? C25 C26 C27 C7 178.7(3) . . . 2_665 ? C10 C11 N1 C8 -0.3(3) . . . . ? C12 C11 N1 C8 179.2(2) . . . . ? C7 C8 N1 C11 -179.0(2) . . . . ? C9 C8 N1 C11 0.0(3) . . . . ? C25 C24 N2 C27 0.0(3) . . . . ? C21 C24 N2 C27 -179.8(2) . . . . ? C26 C27 N2 C24 0.0(3) . . . . ? C7 C27 N2 C24 -178.9(2) 2_665 . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2 N1 0.84(2) 2.10(2) 2.702(3) 129(2) 2_665 _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 21.88 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.173 _refine_diff_density_min -0.134 _refine_diff_density_rms 0.039 _vrf_THETM01_shelxl ; PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550 RESPONSE: The crystal was poorly diffracting. There practically no reflections present for Bragg angles > 20.1 deg. The situation did not improve with recrystallisation and fresh data collection. ; _vrf_PLAT023_shelxl ; PROBLEM: Resolution (too) Low [sin(theta)/Lambda < 0.6].. 21.88 Deg. RESPONSE: The crystal was poorly diffracting. There practically no reflections present for Bragg angles > 20.1 deg. The situation did not improve with recrystallisation and fresh data collection. ; _database_code_depnum_ccdc_archive 'CCDC 926221' ####################################################################### # # 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_publication_text2 data_shelxl2 #TrackingRef 'p1311.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C68 H42 F20 N4 O' _chemical_formula_weight 1311.06 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n 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 18.1032(14) _cell_length_b 13.7944(9) _cell_length_c 27.4477(19) _cell_angle_alpha 90.00 _cell_angle_beta 109.182(2) _cell_angle_gamma 90.00 _cell_volume 6473.8(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5421 _cell_measurement_theta_min 2.6 _cell_measurement_theta_max 22.2 _exptl_crystal_description block _exptl_crystal_colour brown _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.345 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2664 _exptl_absorpt_coefficient_mu 0.120 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.932 _exptl_absorpt_correction_T_max 0.961 _exptl_absorpt_process_details 'SADABS (Bruker, 1999)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 axs kappa apex2 CCD Diffractometer' _diffrn_measurement_method '\w and \f scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 43385 _diffrn_reflns_av_R_equivalents 0.0375 _diffrn_reflns_av_sigmaI/netI 0.0335 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 22.53 _reflns_number_total 8481 _reflns_number_gt 6139 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2004)' _computing_cell_refinement 'APEX2/SAINT (Bruker, 2004)' _computing_data_reduction 'SAINT/XPREP (Bruker, 2004)' _computing_structure_solution 'SIR92 (Altornare et al., 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; calc w=1/[\s^2^(Fo^2^)+(0.1326P)^2^+2.4539P] 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 8481 _refine_ls_number_parameters 854 _refine_ls_number_restraints 122 _refine_ls_R_factor_all 0.0860 _refine_ls_R_factor_gt 0.0663 _refine_ls_wR_factor_ref 0.2110 _refine_ls_wR_factor_gt 0.1961 _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_restrained_S_all 1.280 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.000 # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.000 -0.008 0.000 427 105 ' ' 2 0.500 -0.043 0.500 427 105 ' ' 3 0.455 0.119 0.923 42 1 ' ' 4 0.955 0.381 0.423 42 1 ' ' 5 0.045 0.619 0.577 42 1 ' ' 6 0.545 0.881 0.077 42 1 ' ' _platon_squeeze_details ; Disordered solvent molecules with scattering factor equivalent to 53 electrons per asymmetric unit is removed using the program squeeze(PLATON). As the removed solvent types cannot be confirmed, the same is not added to the formula. ; loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.9484(4) 0.3902(5) 0.1374(3) 0.102(2) Uani 1 1 d . . . C2 C 0.8872(4) 0.3532(7) 0.1501(5) 0.151(4) Uani 1 1 d . . . C3 C 0.8939(4) 0.3349(6) 0.1987(5) 0.122(3) Uani 1 1 d . . . C4 C 0.9617(4) 0.3520(5) 0.2361(3) 0.092(2) Uani 1 1 d . . . C5 C 1.0231(3) 0.3894(4) 0.2234(2) 0.0638(14) Uani 1 1 d . . . C6 C 1.0181(3) 0.4096(3) 0.1738(2) 0.0566(13) Uani 1 1 d . . . C7 C 1.0870(2) 0.4498(3) 0.16111(18) 0.0481(11) Uani 1 1 d . . . C8 C 1.1462(3) 0.3839(3) 0.16224(17) 0.0451(11) Uani 1 1 d . . . C9 C 1.1493(3) 0.2839(3) 0.17154(17) 0.0501(12) Uani 1 1 d . . . H9 H 1.1110 0.2474 0.1788 0.060 Uiso 1 1 calc R . . C10 C 1.2182(3) 0.2489(3) 0.16809(18) 0.0500(12) Uani 1 1 d . . . C11 C 1.2576(3) 0.3309(3) 0.15665(16) 0.0432(11) Uani 1 1 d . . . C12 C 1.2465(3) 0.1439(3) 0.1766(2) 0.0635(15) Uani 1 1 d . . . C13 C 1.1798(5) 0.0804(4) 0.1824(3) 0.113(3) Uani 1 1 d . . . H13A H 1.1689 0.0989 0.2131 0.170 Uiso 1 1 calc R . . H13B H 1.1952 0.0135 0.1848 0.170 Uiso 1 1 calc R . . H13C H 1.1337 0.0893 0.1529 0.170 Uiso 1 1 calc R . . C14 C 1.3171(5) 0.1361(4) 0.2250(2) 0.101(3) Uani 1 1 d . . . H14A H 1.3601 0.1710 0.2202 0.152 Uiso 1 1 calc R . . H14B H 1.3312 0.0692 0.2318 0.152 Uiso 1 1 calc R . . H14C H 1.3047 0.1632 0.2536 0.152 Uiso 1 1 calc R . . C15 C 1.2634(3) 0.1062(3) 0.12843(19) 0.0521(12) Uani 1 1 d . . . C16 C 1.2133(3) 0.1262(3) 0.0796(2) 0.0639(14) Uani 1 1 d . . . H16 H 1.1707 0.1667 0.0756 0.077 Uiso 1 1 calc R . . C17 C 1.2254(3) 0.0872(4) 0.0363(2) 0.0656(14) Uani 1 1 d . . . H17 H 1.1901 0.1012 0.0038 0.079 Uiso 1 1 calc R . . C18 C 1.2884(3) 0.0281(3) 0.04039(19) 0.0557(13) Uani 1 1 d . . . C19 C 1.3373(3) 0.0079(3) 0.08867(19) 0.0598(13) Uani 1 1 d . . . H19 H 1.3799 -0.0328 0.0926 0.072 Uiso 1 1 calc R . . C20 C 1.3255(3) 0.0461(3) 0.13214(19) 0.0596(13) Uani 1 1 d . . . H20 H 1.3604 0.0309 0.1645 0.072 Uiso 1 1 calc R . . C21 C 1.3004(4) -0.0156(3) -0.00793(19) 0.0675(15) Uani 1 1 d . . . C22 C 1.2439(5) -0.0995(4) -0.0262(2) 0.097(2) Uani 1 1 d . . . H22A H 1.1911 -0.0757 -0.0362 0.145 Uiso 1 1 calc R . . H22B H 1.2520 -0.1456 0.0013 0.145 Uiso 1 1 calc R . . H22C H 1.2526 -0.1303 -0.0551 0.145 Uiso 1 1 calc R . . C23 C 1.3850(4) -0.0534(4) 0.0027(2) 0.0859(19) Uani 1 1 d . . . H23A H 1.3907 -0.0767 -0.0288 0.129 Uiso 1 1 calc R . . H23B H 1.3952 -0.1052 0.0274 0.129 Uiso 1 1 calc R . . H23C H 1.4214 -0.0016 0.0162 0.129 Uiso 1 1 calc R . . C24 C 1.2852(3) 0.0600(3) -0.05055(18) 0.0618(14) Uani 1 1 d . . . C25 C 1.2606(4) 0.0423(4) -0.1048(2) 0.0827(19) Uani 1 1 d . . . H25 H 1.2457 -0.0171 -0.1211 0.099 Uiso 1 1 calc R . . C26 C 1.2631(4) 0.1282(4) -0.1281(2) 0.0715(16) Uani 1 1 d . . . H26 H 1.2507 0.1388 -0.1634 0.086 Uiso 1 1 calc R . . C27 C 1.2877(3) 0.1983(3) -0.08903(16) 0.0493(11) Uani 1 1 d . . . C28 C 1.2981(2) 0.2968(3) -0.09310(15) 0.0424(10) Uani 1 1 d . . . C29 C 1.2841(3) 0.3374(3) -0.14567(16) 0.0470(11) Uani 1 1 d . . . C30 C 1.2153(4) 0.3804(4) -0.1729(2) 0.0764(17) Uani 1 1 d . . . C31 C 1.2062(6) 0.4238(5) -0.2218(3) 0.118(3) Uani 1 1 d . . . C32 C 1.2699(8) 0.4186(5) -0.2402(3) 0.113(3) Uani 1 1 d . . . C33 C 1.3341(6) 0.3744(6) -0.2139(3) 0.097(2) Uani 1 1 d . . . C34 C 1.3419(4) 0.3354(4) -0.16835(19) 0.0640(15) Uani 1 1 d . . . C35 C 1.3226(2) 0.3639(3) -0.05217(15) 0.0388(10) Uani 1 1 d . . . C36 C 1.3355(2) 0.4636(3) -0.05387(15) 0.0373(10) Uani 1 1 d . . . H36 H 1.3275 0.5004 -0.0836 0.045 Uiso 1 1 calc R . . C37 C 1.3621(2) 0.4981(3) -0.00380(15) 0.0372(10) Uani 1 1 d . . . C38 C 1.3646(2) 0.4165(3) 0.02811(15) 0.0345(9) Uani 1 1 d . . . C39 C 1.3846(2) 0.6027(3) 0.01259(15) 0.0381(10) Uani 1 1 d . . . C40 C 1.3694(3) 0.6665(3) -0.03553(18) 0.0544(12) Uani 1 1 d . . . H40A H 1.3152 0.6626 -0.0561 0.082 Uiso 1 1 calc R . . H40B H 1.4010 0.6444 -0.0554 0.082 Uiso 1 1 calc R . . H40C H 1.3825 0.7325 -0.0252 0.082 Uiso 1 1 calc R . . C41 C 1.4723(3) 0.6088(3) 0.0415(2) 0.0538(12) Uani 1 1 d . . . H41A H 1.4872 0.6754 0.0485 0.081 Uiso 1 1 calc R . . H41B H 1.5004 0.5810 0.0207 0.081 Uiso 1 1 calc R . . H41C H 1.4845 0.5737 0.0733 0.081 Uiso 1 1 calc R . . C42 C 1.3350(2) 0.6413(3) 0.04336(15) 0.0383(10) Uani 1 1 d . . . C43 C 1.3641(3) 0.7012(3) 0.08581(16) 0.0458(11) Uani 1 1 d . . . H43 H 1.4171 0.7160 0.0978 0.055 Uiso 1 1 calc R . . C44 C 1.3150(3) 0.7397(3) 0.11091(18) 0.0500(12) Uani 1 1 d . . . H44 H 1.3364 0.7800 0.1392 0.060 Uiso 1 1 calc R . . C45 C 1.2371(3) 0.7204(3) 0.09538(17) 0.0456(11) Uani 1 1 d . . . C46 C 1.2074(3) 0.6608(3) 0.05241(18) 0.0497(11) Uani 1 1 d . . . H46 H 1.1542 0.6470 0.0404 0.060 Uiso 1 1 calc R . . C47 C 1.2553(2) 0.6217(3) 0.02729(17) 0.0462(11) Uani 1 1 d . . . H47 H 1.2337 0.5814 -0.0010 0.055 Uiso 1 1 calc R . . C48 C 1.1821(3) 0.7635(3) 0.1212(2) 0.0554(13) Uani 1 1 d . . . C49 C 1.1339(4) 0.8443(4) 0.0856(3) 0.0824(19) Uani 1 1 d . . . H49A H 1.1687 0.8883 0.0769 0.124 Uiso 1 1 calc R . . H49B H 1.1041 0.8788 0.1031 0.124 Uiso 1 1 calc R . . H49C H 1.0992 0.8157 0.0546 0.124 Uiso 1 1 calc R . . C50 C 1.2275(3) 0.8079(4) 0.1741(2) 0.0728(16) Uani 1 1 d . . . H50A H 1.2599 0.7591 0.1958 0.109 Uiso 1 1 calc R . . H50B H 1.1911 0.8320 0.1900 0.109 Uiso 1 1 calc R . . H50C H 1.2596 0.8601 0.1696 0.109 Uiso 1 1 calc R . . C51 C 1.1274(3) 0.6886(3) 0.13023(18) 0.0510(12) Uani 1 1 d . . . C52 C 1.0541(3) 0.7045(4) 0.1368(2) 0.0717(16) Uani 1 1 d . . . H52 H 1.0283 0.7637 0.1336 0.086 Uiso 1 1 calc R . . C53 C 1.0279(3) 0.6185(4) 0.1488(2) 0.0691(15) Uani 1 1 d . . . H53 H 0.9811 0.6077 0.1550 0.083 Uiso 1 1 calc R . . C54 C 1.0853(2) 0.5483(3) 0.14985(18) 0.0471(11) Uani 1 1 d . . . C55 C 1.3363(3) 0.3376(3) 0.14958(16) 0.0430(10) Uani 1 1 d . . . H55 H 1.3571 0.2716 0.1512 0.052 Uiso 1 1 calc R . . C56 C 1.3941(3) 0.3967(4) 0.19254(16) 0.0509(12) Uani 1 1 d . . . C57 C 1.3884(3) 0.4958(4) 0.19847(19) 0.0560(13) Uani 1 1 d . . . C58 C 1.4405(4) 0.5473(5) 0.2381(3) 0.0801(18) Uani 1 1 d . . . C59 C 1.4997(5) 0.5015(9) 0.2741(3) 0.106(3) Uani 1 1 d . . . C60 C 1.5084(4) 0.4031(9) 0.2689(2) 0.108(3) Uani 1 1 d . . . C61 C 1.4573(3) 0.3513(5) 0.2288(2) 0.0774(17) Uani 1 1 d . . . C62 C 1.3898(2) 0.4098(3) 0.08597(15) 0.0364(9) Uani 1 1 d . . . H62 H 1.4012 0.4756 0.0999 0.044 Uiso 1 1 calc R . . C63 C 1.4639(2) 0.3487(3) 0.10841(15) 0.0400(10) Uani 1 1 d . . . C64 C 1.5323(3) 0.3908(3) 0.13945(17) 0.0482(11) Uani 1 1 d . . . C65 C 1.6009(3) 0.3402(4) 0.16007(19) 0.0595(13) Uani 1 1 d . . . C66 C 1.6031(3) 0.2446(5) 0.1500(2) 0.0698(15) Uani 1 1 d . . . C67 C 1.5368(3) 0.1987(3) 0.1205(2) 0.0584(13) Uani 1 1 d . . . C68 C 1.4684(3) 0.2506(3) 0.10054(16) 0.0448(11) Uani 1 1 d . . . N1 N 1.2139(2) 0.4108(2) 0.15324(14) 0.0435(9) Uani 1 1 d D . . N2 N 1.3017(3) 0.1526(3) -0.04159(14) 0.0572(11) Uani 1 1 d . . . N3 N 1.3409(2) 0.3376(2) -0.00140(12) 0.0400(8) Uani 1 1 d D . . N4 N 1.1463(2) 0.5952(2) 0.13855(14) 0.0460(9) Uani 1 1 d . . . O1 O 1.32403(16) 0.3739(2) 0.09891(10) 0.0417(7) Uani 1 1 d . . . F1 F 0.9382(3) 0.4101(5) 0.0880(2) 0.174(2) Uani 1 1 d U . . F2 F 0.8187(3) 0.3361(7) 0.1123(3) 0.254(4) Uani 1 1 d U . . F3 F 0.8331(3) 0.3009(4) 0.2114(3) 0.193(3) Uani 1 1 d U . . F4 F 0.9713(3) 0.3347(4) 0.2861(2) 0.1535(19) Uani 1 1 d U . . F5 F 1.0917(2) 0.4033(3) 0.26154(13) 0.1027(12) Uani 1 1 d U . . F6 F 1.4095(2) 0.2906(3) -0.14394(14) 0.1066(13) Uani 1 1 d U . . F7 F 1.3927(3) 0.3734(4) -0.23397(17) 0.159(2) Uani 1 1 d U . . F8 F 1.2556(5) 0.4649(3) -0.28532(15) 0.186(3) Uani 1 1 d U . . F9 F 1.1391(4) 0.4650(4) -0.2467(2) 0.203(3) Uani 1 1 d U . . F10 F 1.1582(2) 0.3854(4) -0.15320(16) 0.1311(16) Uani 1 1 d U . . F11 F 1.4714(2) 0.2581(3) 0.22455(14) 0.1064(13) Uani 1 1 d U . . F12 F 1.5684(3) 0.3540(5) 0.30279(18) 0.163(2) Uani 1 1 d U . . F13 F 1.5494(3) 0.5488(5) 0.31285(15) 0.159(2) Uani 1 1 d U . . F14 F 1.4322(2) 0.6422(3) 0.24154(16) 0.1172(15) Uani 1 1 d U . . F15 F 1.33262(16) 0.54586(18) 0.16454(12) 0.0669(8) Uani 1 1 d U . . F16 F 1.40466(16) 0.20084(17) 0.07363(10) 0.0609(7) Uani 1 1 d U . . F17 F 1.5375(2) 0.1038(2) 0.11051(14) 0.0896(10) Uani 1 1 d U . . F18 F 1.67031(19) 0.1947(3) 0.16791(16) 0.1075(12) Uani 1 1 d U . . F19 F 1.66569(18) 0.3855(3) 0.18937(15) 0.0991(11) Uani 1 1 d U . . F20 F 1.53410(15) 0.4852(2) 0.15212(10) 0.0644(8) Uani 1 1 d U . . H1A H 1.223(3) 0.4725(17) 0.146(2) 0.09(2) Uiso 1 1 d D . . H3A H 1.327(4) 0.281(3) 0.009(2) 0.11(2) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.062(4) 0.128(6) 0.099(5) 0.048(4) 0.002(4) -0.031(4) C2 0.037(4) 0.183(9) 0.194(10) 0.091(8) -0.015(5) -0.032(4) C3 0.052(4) 0.110(6) 0.217(10) 0.080(6) 0.062(6) 0.010(4) C4 0.100(6) 0.078(4) 0.130(6) 0.022(4) 0.082(5) 0.004(4) C5 0.062(3) 0.061(3) 0.082(4) 0.004(3) 0.042(3) -0.009(3) C6 0.048(3) 0.047(3) 0.079(4) 0.012(3) 0.026(3) -0.002(2) C7 0.049(3) 0.045(3) 0.058(3) -0.001(2) 0.027(2) -0.008(2) C8 0.055(3) 0.037(3) 0.052(3) -0.004(2) 0.030(2) -0.006(2) C9 0.068(3) 0.037(3) 0.060(3) -0.004(2) 0.041(2) -0.009(2) C10 0.078(3) 0.034(2) 0.054(3) 0.000(2) 0.044(3) 0.001(2) C11 0.062(3) 0.035(2) 0.043(2) 0.0028(19) 0.032(2) 0.006(2) C12 0.114(4) 0.034(3) 0.068(3) 0.007(2) 0.065(3) 0.009(3) C13 0.200(8) 0.036(3) 0.176(7) -0.002(4) 0.158(7) -0.007(4) C14 0.207(8) 0.060(4) 0.051(3) 0.017(3) 0.063(4) 0.057(4) C15 0.089(4) 0.028(2) 0.056(3) 0.004(2) 0.046(3) -0.002(2) C16 0.088(4) 0.044(3) 0.074(4) 0.000(3) 0.046(3) 0.005(3) C17 0.095(4) 0.053(3) 0.051(3) -0.001(2) 0.028(3) -0.004(3) C18 0.093(4) 0.026(2) 0.061(3) -0.004(2) 0.043(3) 0.002(2) C19 0.098(4) 0.039(3) 0.058(3) 0.004(2) 0.047(3) 0.012(3) C20 0.099(4) 0.040(3) 0.053(3) 0.007(2) 0.042(3) 0.011(3) C21 0.121(5) 0.037(3) 0.059(3) -0.006(2) 0.048(3) -0.008(3) C22 0.176(7) 0.047(3) 0.081(4) -0.014(3) 0.062(5) -0.030(4) C23 0.137(6) 0.069(4) 0.076(4) 0.000(3) 0.066(4) 0.030(4) C24 0.109(4) 0.038(3) 0.049(3) -0.009(2) 0.041(3) -0.006(3) C25 0.156(6) 0.041(3) 0.059(4) -0.016(3) 0.047(4) -0.020(3) C26 0.124(5) 0.051(3) 0.044(3) -0.008(2) 0.034(3) -0.019(3) C27 0.076(3) 0.040(3) 0.038(3) -0.003(2) 0.027(2) -0.005(2) C28 0.053(3) 0.044(3) 0.036(2) 0.001(2) 0.023(2) 0.002(2) C29 0.067(3) 0.041(3) 0.033(2) -0.006(2) 0.016(2) -0.005(2) C30 0.090(4) 0.081(4) 0.053(3) 0.001(3) 0.016(3) 0.028(3) C31 0.173(8) 0.068(4) 0.064(5) -0.005(4) -0.027(5) 0.050(5) C32 0.240(12) 0.052(4) 0.046(4) 0.000(3) 0.044(6) -0.020(6) C33 0.164(7) 0.092(5) 0.053(4) -0.016(4) 0.058(5) -0.066(5) C34 0.094(4) 0.066(3) 0.040(3) -0.014(3) 0.032(3) -0.029(3) C35 0.054(3) 0.034(2) 0.033(2) -0.0003(19) 0.0206(19) 0.0023(19) C36 0.048(2) 0.038(2) 0.032(2) 0.0026(18) 0.0212(19) 0.0020(18) C37 0.042(2) 0.034(2) 0.042(2) 0.000(2) 0.0229(19) 0.0036(18) C38 0.044(2) 0.030(2) 0.035(2) 0.0019(19) 0.0213(18) 0.0018(17) C39 0.046(2) 0.033(2) 0.042(2) 0.0001(19) 0.023(2) 0.0006(18) C40 0.084(3) 0.037(2) 0.054(3) 0.005(2) 0.039(3) 0.001(2) C41 0.052(3) 0.043(3) 0.074(3) -0.008(2) 0.033(2) -0.003(2) C42 0.050(3) 0.029(2) 0.041(2) 0.0032(19) 0.023(2) 0.0034(18) C43 0.049(3) 0.043(3) 0.049(3) -0.004(2) 0.021(2) -0.005(2) C44 0.068(3) 0.040(3) 0.053(3) -0.011(2) 0.034(2) -0.006(2) C45 0.066(3) 0.028(2) 0.054(3) 0.004(2) 0.036(2) 0.005(2) C46 0.047(3) 0.048(3) 0.059(3) 0.000(2) 0.025(2) 0.000(2) C47 0.050(3) 0.043(3) 0.049(3) -0.007(2) 0.021(2) -0.001(2) C48 0.082(3) 0.031(2) 0.074(3) 0.006(2) 0.053(3) 0.008(2) C49 0.106(4) 0.058(3) 0.115(5) 0.032(3) 0.078(4) 0.036(3) C50 0.103(4) 0.049(3) 0.094(4) -0.024(3) 0.071(4) -0.016(3) C51 0.067(3) 0.036(3) 0.063(3) 0.005(2) 0.040(2) 0.010(2) C52 0.071(3) 0.051(3) 0.114(5) 0.022(3) 0.058(3) 0.022(3) C53 0.053(3) 0.065(4) 0.101(4) 0.017(3) 0.043(3) 0.010(3) C54 0.047(3) 0.039(3) 0.062(3) 0.003(2) 0.027(2) -0.001(2) C55 0.059(3) 0.037(2) 0.041(2) 0.009(2) 0.029(2) 0.015(2) C56 0.054(3) 0.073(3) 0.034(2) 0.005(2) 0.025(2) 0.005(2) C57 0.055(3) 0.075(4) 0.050(3) -0.013(3) 0.033(3) -0.007(3) C58 0.078(4) 0.111(6) 0.072(4) -0.035(4) 0.052(4) -0.030(4) C59 0.081(5) 0.194(9) 0.050(4) -0.034(5) 0.030(4) -0.047(6) C60 0.059(4) 0.217(10) 0.039(4) 0.025(5) 0.005(3) -0.005(5) C61 0.068(4) 0.116(5) 0.053(4) 0.030(4) 0.026(3) 0.023(4) C62 0.045(2) 0.032(2) 0.038(2) -0.0013(18) 0.0205(19) 0.0014(17) C63 0.053(3) 0.042(3) 0.033(2) 0.0056(19) 0.024(2) 0.001(2) C64 0.057(3) 0.048(3) 0.044(3) 0.001(2) 0.024(2) 0.001(2) C65 0.048(3) 0.069(4) 0.060(3) 0.004(3) 0.016(2) -0.003(3) C66 0.057(3) 0.083(4) 0.071(4) 0.024(3) 0.023(3) 0.025(3) C67 0.074(4) 0.039(3) 0.069(3) 0.010(2) 0.032(3) 0.019(3) C68 0.058(3) 0.042(3) 0.039(2) 0.002(2) 0.021(2) 0.001(2) N1 0.054(2) 0.028(2) 0.059(2) 0.0033(18) 0.0327(18) 0.0003(17) N2 0.097(3) 0.035(2) 0.046(2) -0.0024(18) 0.032(2) -0.007(2) N3 0.061(2) 0.031(2) 0.033(2) -0.0012(17) 0.0222(17) -0.0040(17) N4 0.055(2) 0.037(2) 0.058(2) 0.0021(17) 0.0337(19) 0.0045(16) O1 0.0505(17) 0.0450(17) 0.0367(16) 0.0055(13) 0.0242(13) 0.0019(13) F1 0.138(4) 0.229(5) 0.109(3) 0.053(3) -0.022(3) -0.082(4) F2 0.089(3) 0.327(8) 0.280(7) 0.128(6) -0.029(4) -0.081(4) F3 0.084(3) 0.199(5) 0.324(7) 0.116(5) 0.108(4) -0.001(3) F4 0.193(5) 0.165(4) 0.157(4) 0.021(3) 0.132(4) -0.030(3) F5 0.117(3) 0.123(3) 0.073(2) -0.010(2) 0.038(2) -0.052(2) F6 0.072(2) 0.171(4) 0.085(2) -0.034(2) 0.0364(19) -0.005(2) F7 0.216(5) 0.203(5) 0.105(3) -0.056(3) 0.116(3) -0.119(4) F8 0.381(7) 0.112(3) 0.054(2) 0.017(2) 0.056(3) -0.060(4) F9 0.257(6) 0.177(5) 0.112(4) 0.019(3) -0.027(4) 0.118(5) F10 0.081(2) 0.197(4) 0.105(3) -0.013(3) 0.018(2) 0.061(3) F11 0.095(2) 0.127(3) 0.098(3) 0.058(2) 0.032(2) 0.048(2) F12 0.101(3) 0.263(6) 0.094(3) 0.061(3) -0.010(3) 0.003(3) F13 0.133(3) 0.270(6) 0.068(2) -0.043(3) 0.024(2) -0.087(4) F14 0.128(3) 0.122(3) 0.131(3) -0.072(3) 0.083(3) -0.064(3) F15 0.0654(18) 0.0472(15) 0.096(2) -0.0100(15) 0.0374(17) -0.0027(13) F16 0.0760(18) 0.0384(14) 0.0642(17) 0.0017(13) 0.0172(14) 0.0028(13) F17 0.103(2) 0.0551(19) 0.108(3) 0.0074(17) 0.031(2) 0.0314(16) F18 0.070(2) 0.112(3) 0.130(3) 0.027(2) 0.018(2) 0.038(2) F19 0.060(2) 0.106(3) 0.109(3) 0.002(2) -0.0031(19) -0.0037(18) F20 0.0672(17) 0.0566(18) 0.0630(17) -0.0083(14) 0.0127(14) -0.0093(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 C1 F1 1.336(8) . ? C1 C6 1.353(8) . ? C1 C2 1.364(11) . ? C2 C3 1.322(13) . ? C2 F2 1.350(9) . ? C3 C4 1.338(11) . ? C3 F3 1.346(8) . ? C4 F4 1.346(8) . ? C4 C5 1.371(8) . ? C5 F5 1.350(6) . ? C5 C6 1.363(7) . ? C6 C7 1.506(6) . ? C7 C54 1.392(6) . ? C7 C8 1.398(6) . ? C8 N1 1.379(5) . ? C8 C9 1.400(6) . ? C9 C10 1.369(6) . ? C9 H9 0.9300 . ? C10 C11 1.427(6) . ? C10 C12 1.529(6) . ? C11 N1 1.342(5) . ? C11 C55 1.502(6) . ? C12 C14 1.514(9) . ? C12 C15 1.541(6) . ? C12 C13 1.543(8) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 C20 1.374(7) . ? C15 C16 1.377(7) . ? C16 C17 1.385(7) . ? C16 H16 0.9300 . ? C17 C18 1.378(7) . ? C17 H17 0.9300 . ? C18 C19 1.359(7) . ? C18 C21 1.535(7) . ? C19 C20 1.384(7) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? C21 C22 1.517(8) . ? C21 C24 1.523(7) . ? C21 C23 1.552(8) . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 N2 1.316(6) . ? C24 C25 1.429(7) . ? C25 C26 1.354(7) . ? C25 H25 0.9300 . ? C26 C27 1.404(6) . ? C26 H26 0.9300 . ? C27 C28 1.380(6) . ? C27 N2 1.394(6) . ? C28 C35 1.410(6) . ? C28 C29 1.490(6) . ? C29 C30 1.360(7) . ? C29 C34 1.384(7) . ? C30 F10 1.315(7) . ? C30 C31 1.430(11) . ? C31 F9 1.311(9) . ? C31 C32 1.405(13) . ? C32 C33 1.301(12) . ? C32 F8 1.340(8) . ? C33 C34 1.325(8) . ? C33 F7 1.345(9) . ? C34 F6 1.337(7) . ? C35 N3 1.371(5) . ? C35 C36 1.398(6) . ? C36 C37 1.383(6) . ? C36 H36 0.9300 . ? C37 C38 1.418(5) . ? C37 C39 1.527(6) . ? C38 N3 1.340(5) . ? C38 C62 1.504(6) . ? C39 C42 1.517(6) . ? C39 C41 1.526(6) . ? C39 C40 1.535(6) . ? C40 H40A 0.9600 . ? C40 H40B 0.9600 . ? C40 H40C 0.9600 . ? C41 H41A 0.9600 . ? C41 H41B 0.9600 . ? C41 H41C 0.9600 . ? C42 C43 1.384(6) . ? C42 C47 1.389(6) . ? C43 C44 1.396(6) . ? C43 H43 0.9300 . ? C44 C45 1.358(6) . ? C44 H44 0.9300 . ? C45 C46 1.393(6) . ? C45 C48 1.521(6) . ? C46 C47 1.383(6) . ? C46 H46 0.9300 . ? C47 H47 0.9300 . ? C48 C51 1.507(6) . ? C48 C50 1.540(7) . ? C48 C49 1.549(7) . ? C49 H49A 0.9600 . ? C49 H49B 0.9600 . ? C49 H49C 0.9600 . ? C50 H50A 0.9600 . ? C50 H50B 0.9600 . ? C50 H50C 0.9600 . ? C51 N4 1.333(5) . ? C51 C52 1.415(7) . ? C52 C53 1.357(7) . ? C52 H52 0.9300 . ? C53 C54 1.412(6) . ? C53 H53 0.9300 . ? C54 N4 1.401(5) . ? C55 O1 1.425(5) . ? C55 C56 1.530(7) . ? C55 H55 0.9800 . ? C56 C57 1.384(7) . ? C56 C61 1.394(7) . ? C57 F15 1.321(6) . ? C57 C58 1.379(8) . ? C58 F14 1.325(8) . ? C58 C59 1.352(11) . ? C59 F13 1.320(8) . ? C59 C60 1.379(12) . ? C60 F12 1.356(8) . ? C60 C61 1.382(10) . ? C61 F11 1.323(7) . ? C62 O1 1.437(5) . ? C62 C63 1.532(6) . ? C62 H62 0.9800 . ? C63 C68 1.377(6) . ? C63 C64 1.380(6) . ? C64 F20 1.345(5) . ? C64 C65 1.374(7) . ? C65 F19 1.339(6) . ? C65 C66 1.351(8) . ? C66 F18 1.343(6) . ? C66 C67 1.363(7) . ? C67 F17 1.338(5) . ? C67 C68 1.378(6) . ? C68 F16 1.337(5) . ? N1 H1A 0.899(12) . ? N3 H3A 0.896(12) . ? 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 F1 C1 C6 119.4(6) . . ? F1 C1 C2 118.9(7) . . ? C6 C1 C2 121.6(7) . . ? C3 C2 F2 119.8(8) . . ? C3 C2 C1 121.0(7) . . ? F2 C2 C1 119.2(10) . . ? C2 C3 C4 119.9(6) . . ? C2 C3 F3 121.1(9) . . ? C4 C3 F3 118.9(10) . . ? C3 C4 F4 122.1(7) . . ? C3 C4 C5 119.0(7) . . ? F4 C4 C5 118.9(7) . . ? F5 C5 C6 119.2(4) . . ? F5 C5 C4 118.1(6) . . ? C6 C5 C4 122.6(6) . . ? C1 C6 C5 115.8(5) . . ? C1 C6 C7 123.0(5) . . ? C5 C6 C7 121.1(4) . . ? C54 C7 C8 126.9(4) . . ? C54 C7 C6 116.8(4) . . ? C8 C7 C6 116.3(4) . . ? N1 C8 C7 122.7(4) . . ? N1 C8 C9 108.3(4) . . ? C7 C8 C9 129.0(4) . . ? C10 C9 C8 108.5(4) . . ? C10 C9 H9 125.7 . . ? C8 C9 H9 125.7 . . ? C9 C10 C11 105.6(4) . . ? C9 C10 C12 126.3(4) . . ? C11 C10 C12 128.1(4) . . ? N1 C11 C10 109.9(4) . . ? N1 C11 C55 120.2(4) . . ? C10 C11 C55 129.9(4) . . ? C14 C12 C10 110.2(4) . . ? C14 C12 C15 112.4(4) . . ? C10 C12 C15 109.9(4) . . ? C14 C12 C13 109.4(5) . . ? C10 C12 C13 108.6(4) . . ? C15 C12 C13 106.2(4) . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C12 C14 H14A 109.5 . . ? C12 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C12 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C20 C15 C16 117.0(4) . . ? C20 C15 C12 121.9(5) . . ? C16 C15 C12 121.0(4) . . ? C15 C16 C17 121.2(5) . . ? C15 C16 H16 119.4 . . ? C17 C16 H16 119.4 . . ? C18 C17 C16 121.3(5) . . ? C18 C17 H17 119.3 . . ? C16 C17 H17 119.3 . . ? C19 C18 C17 117.2(4) . . ? C19 C18 C21 122.0(5) . . ? C17 C18 C21 120.7(5) . . ? C18 C19 C20 121.8(5) . . ? C18 C19 H19 119.1 . . ? C20 C19 H19 119.1 . . ? C15 C20 C19 121.4(5) . . ? C15 C20 H20 119.3 . . ? C19 C20 H20 119.3 . . ? C22 C21 C24 109.7(5) . . ? C22 C21 C18 108.2(4) . . ? C24 C21 C18 110.7(4) . . ? C22 C21 C23 108.9(5) . . ? C24 C21 C23 107.0(4) . . ? C18 C21 C23 112.3(5) . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C21 C23 H23A 109.5 . . ? C21 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C21 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? N2 C24 C25 109.5(4) . . ? N2 C24 C21 123.2(4) . . ? C25 C24 C21 126.9(4) . . ? C26 C25 C24 107.2(4) . . ? C26 C25 H25 126.4 . . ? C24 C25 H25 126.4 . . ? C25 C26 C27 107.1(4) . . ? C25 C26 H26 126.5 . . ? C27 C26 H26 126.5 . . ? C28 C27 N2 122.2(4) . . ? C28 C27 C26 129.3(4) . . ? N2 C27 C26 108.4(4) . . ? C27 C28 C35 126.7(4) . . ? C27 C28 C29 117.6(4) . . ? C35 C28 C29 115.7(4) . . ? C30 C29 C34 117.0(5) . . ? C30 C29 C28 121.9(4) . . ? C34 C29 C28 121.0(4) . . ? F10 C30 C29 119.9(5) . . ? F10 C30 C31 120.1(6) . . ? C29 C30 C31 120.0(7) . . ? F9 C31 C32 124.3(10) . . ? F9 C31 C30 118.1(10) . . ? C32 C31 C30 117.6(6) . . ? C33 C32 F8 127.1(11) . . ? C33 C32 C31 120.8(7) . . ? F8 C32 C31 112.1(11) . . ? C32 C33 C34 120.9(8) . . ? C32 C33 F7 117.2(8) . . ? C34 C33 F7 121.8(9) . . ? C33 C34 F6 117.2(6) . . ? C33 C34 C29 123.7(7) . . ? F6 C34 C29 119.1(4) . . ? N3 C35 C36 107.9(3) . . ? N3 C35 C28 122.9(4) . . ? C36 C35 C28 129.2(4) . . ? C37 C36 C35 108.2(3) . . ? C37 C36 H36 125.9 . . ? C35 C36 H36 125.9 . . ? C36 C37 C38 105.7(3) . . ? C36 C37 C39 126.1(3) . . ? C38 C37 C39 128.1(4) . . ? N3 C38 C37 109.4(3) . . ? N3 C38 C62 120.9(3) . . ? C37 C38 C62 129.6(4) . . ? C42 C39 C41 113.4(3) . . ? C42 C39 C37 110.2(3) . . ? C41 C39 C37 109.7(3) . . ? C42 C39 C40 107.8(3) . . ? C41 C39 C40 106.1(4) . . ? C37 C39 C40 109.5(3) . . ? C39 C40 H40A 109.5 . . ? C39 C40 H40B 109.5 . . ? H40A C40 H40B 109.5 . . ? C39 C40 H40C 109.5 . . ? H40A C40 H40C 109.5 . . ? H40B C40 H40C 109.5 . . ? C39 C41 H41A 109.5 . . ? C39 C41 H41B 109.5 . . ? H41A C41 H41B 109.5 . . ? C39 C41 H41C 109.5 . . ? H41A C41 H41C 109.5 . . ? H41B C41 H41C 109.5 . . ? C43 C42 C47 116.8(4) . . ? C43 C42 C39 123.2(4) . . ? C47 C42 C39 119.9(4) . . ? C42 C43 C44 121.0(4) . . ? C42 C43 H43 119.5 . . ? C44 C43 H43 119.5 . . ? C45 C44 C43 122.3(4) . . ? C45 C44 H44 118.9 . . ? C43 C44 H44 118.9 . . ? C44 C45 C46 117.0(4) . . ? C44 C45 C48 123.2(4) . . ? C46 C45 C48 119.7(4) . . ? C47 C46 C45 121.4(4) . . ? C47 C46 H46 119.3 . . ? C45 C46 H46 119.3 . . ? C46 C47 C42 121.5(4) . . ? C46 C47 H47 119.3 . . ? C42 C47 H47 119.3 . . ? C51 C48 C45 112.0(4) . . ? C51 C48 C50 107.0(4) . . ? C45 C48 C50 111.5(4) . . ? C51 C48 C49 109.4(4) . . ? C45 C48 C49 107.8(4) . . ? C50 C48 C49 109.0(4) . . ? C48 C49 H49A 109.5 . . ? C48 C49 H49B 109.5 . . ? H49A C49 H49B 109.5 . . ? C48 C49 H49C 109.5 . . ? H49A C49 H49C 109.5 . . ? H49B C49 H49C 109.5 . . ? C48 C50 H50A 109.5 . . ? C48 C50 H50B 109.5 . . ? H50A C50 H50B 109.5 . . ? C48 C50 H50C 109.5 . . ? H50A C50 H50C 109.5 . . ? H50B C50 H50C 109.5 . . ? N4 C51 C52 109.1(4) . . ? N4 C51 C48 123.1(4) . . ? C52 C51 C48 127.5(4) . . ? C53 C52 C51 108.2(4) . . ? C53 C52 H52 125.9 . . ? C51 C52 H52 125.9 . . ? C52 C53 C54 107.0(4) . . ? C52 C53 H53 126.5 . . ? C54 C53 H53 126.5 . . ? C7 C54 N4 122.6(4) . . ? C7 C54 C53 129.5(4) . . ? N4 C54 C53 107.9(4) . . ? O1 C55 C11 107.3(3) . . ? O1 C55 C56 114.4(3) . . ? C11 C55 C56 111.8(3) . . ? O1 C55 H55 107.7 . . ? C11 C55 H55 107.7 . . ? C56 C55 H55 107.7 . . ? C57 C56 C61 115.8(5) . . ? C57 C56 C55 123.9(4) . . ? C61 C56 C55 120.3(5) . . ? F15 C57 C58 116.9(5) . . ? F15 C57 C56 120.2(4) . . ? C58 C57 C56 122.8(6) . . ? F14 C58 C59 119.4(7) . . ? F14 C58 C57 120.1(7) . . ? C59 C58 C57 120.5(7) . . ? F13 C59 C58 121.7(10) . . ? F13 C59 C60 119.9(10) . . ? C58 C59 C60 118.4(6) . . ? F12 C60 C59 121.0(9) . . ? F12 C60 C61 117.6(10) . . ? C59 C60 C61 121.4(7) . . ? F11 C61 C60 118.4(6) . . ? F11 C61 C56 120.7(6) . . ? C60 C61 C56 120.9(7) . . ? O1 C62 C38 107.1(3) . . ? O1 C62 C63 113.4(3) . . ? C38 C62 C63 112.3(3) . . ? O1 C62 H62 107.9 . . ? C38 C62 H62 107.9 . . ? C63 C62 H62 107.9 . . ? C68 C63 C64 115.1(4) . . ? C68 C63 C62 124.5(4) . . ? C64 C63 C62 120.4(4) . . ? F20 C64 C65 116.3(4) . . ? F20 C64 C63 120.6(4) . . ? C65 C64 C63 123.1(4) . . ? F19 C65 C66 120.0(5) . . ? F19 C65 C64 120.4(5) . . ? C66 C65 C64 119.7(5) . . ? F18 C66 C65 120.6(5) . . ? F18 C66 C67 119.6(5) . . ? C65 C66 C67 119.7(4) . . ? F17 C67 C66 120.7(4) . . ? F17 C67 C68 119.6(5) . . ? C66 C67 C68 119.7(4) . . ? F16 C68 C63 120.4(4) . . ? F16 C68 C67 116.9(4) . . ? C63 C68 C67 122.6(4) . . ? C11 N1 C8 107.7(3) . . ? C11 N1 H1A 131(4) . . ? C8 N1 H1A 122(4) . . ? C24 N2 C27 107.7(4) . . ? C38 N3 C35 108.8(3) . . ? C38 N3 H3A 125(4) . . ? C35 N3 H3A 125(4) . . ? C51 N4 C54 107.9(3) . . ? C55 O1 C62 119.1(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 F1 C1 C2 C3 -178.2(9) . . . . ? C6 C1 C2 C3 0.0(15) . . . . ? F1 C1 C2 F2 1.2(15) . . . . ? C6 C1 C2 F2 179.4(8) . . . . ? F2 C2 C3 C4 -179.9(9) . . . . ? C1 C2 C3 C4 -0.5(16) . . . . ? F2 C2 C3 F3 -1.2(16) . . . . ? C1 C2 C3 F3 178.1(8) . . . . ? C2 C3 C4 F4 179.8(8) . . . . ? F3 C3 C4 F4 1.2(11) . . . . ? C2 C3 C4 C5 0.6(12) . . . . ? F3 C3 C4 C5 -178.0(6) . . . . ? C3 C4 C5 F5 -178.0(6) . . . . ? F4 C4 C5 F5 2.8(9) . . . . ? C3 C4 C5 C6 -0.3(10) . . . . ? F4 C4 C5 C6 -179.5(5) . . . . ? F1 C1 C6 C5 178.5(7) . . . . ? C2 C1 C6 C5 0.4(11) . . . . ? F1 C1 C6 C7 -2.3(10) . . . . ? C2 C1 C6 C7 179.5(7) . . . . ? F5 C5 C6 C1 177.5(5) . . . . ? C4 C5 C6 C1 -0.2(8) . . . . ? F5 C5 C6 C7 -1.7(7) . . . . ? C4 C5 C6 C7 -179.4(5) . . . . ? C1 C6 C7 C54 77.4(7) . . . . ? C5 C6 C7 C54 -103.5(6) . . . . ? C1 C6 C7 C8 -103.0(6) . . . . ? C5 C6 C7 C8 76.2(6) . . . . ? C54 C7 C8 N1 1.9(7) . . . . ? C6 C7 C8 N1 -177.7(4) . . . . ? C54 C7 C8 C9 -177.5(5) . . . . ? C6 C7 C8 C9 2.9(7) . . . . ? N1 C8 C9 C10 -0.3(5) . . . . ? C7 C8 C9 C10 179.2(5) . . . . ? C8 C9 C10 C11 0.3(5) . . . . ? C8 C9 C10 C12 178.7(4) . . . . ? C9 C10 C11 N1 -0.3(5) . . . . ? C12 C10 C11 N1 -178.5(4) . . . . ? C9 C10 C11 C55 178.6(4) . . . . ? C12 C10 C11 C55 0.3(8) . . . . ? C9 C10 C12 C14 -112.1(6) . . . . ? C11 C10 C12 C14 65.8(6) . . . . ? C9 C10 C12 C15 123.5(5) . . . . ? C11 C10 C12 C15 -58.6(7) . . . . ? C9 C10 C12 C13 7.7(7) . . . . ? C11 C10 C12 C13 -174.4(5) . . . . ? C14 C12 C15 C20 18.8(6) . . . . ? C10 C12 C15 C20 141.9(5) . . . . ? C13 C12 C15 C20 -100.8(6) . . . . ? C14 C12 C15 C16 -165.6(5) . . . . ? C10 C12 C15 C16 -42.5(6) . . . . ? C13 C12 C15 C16 74.8(6) . . . . ? C20 C15 C16 C17 0.2(7) . . . . ? C12 C15 C16 C17 -175.6(4) . . . . ? C15 C16 C17 C18 -1.0(8) . . . . ? C16 C17 C18 C19 1.5(7) . . . . ? C16 C17 C18 C21 179.3(5) . . . . ? C17 C18 C19 C20 -1.2(7) . . . . ? C21 C18 C19 C20 -178.9(4) . . . . ? C16 C15 C20 C19 0.2(7) . . . . ? C12 C15 C20 C19 175.9(4) . . . . ? C18 C19 C20 C15 0.4(8) . . . . ? C19 C18 C21 C22 100.9(6) . . . . ? C17 C18 C21 C22 -76.8(6) . . . . ? C19 C18 C21 C24 -138.9(5) . . . . ? C17 C18 C21 C24 43.5(6) . . . . ? C19 C18 C21 C23 -19.3(7) . . . . ? C17 C18 C21 C23 163.0(5) . . . . ? C22 C21 C24 N2 153.4(5) . . . . ? C18 C21 C24 N2 34.0(7) . . . . ? C23 C21 C24 N2 -88.7(6) . . . . ? C22 C21 C24 C25 -34.4(8) . . . . ? C18 C21 C24 C25 -153.8(6) . . . . ? C23 C21 C24 C25 83.6(7) . . . . ? N2 C24 C25 C26 0.1(7) . . . . ? C21 C24 C25 C26 -173.1(6) . . . . ? C24 C25 C26 C27 -0.8(7) . . . . ? C25 C26 C27 C28 -178.8(5) . . . . ? C25 C26 C27 N2 1.3(7) . . . . ? N2 C27 C28 C35 -0.6(7) . . . . ? C26 C27 C28 C35 179.6(5) . . . . ? N2 C27 C28 C29 177.9(4) . . . . ? C26 C27 C28 C29 -2.0(8) . . . . ? C27 C28 C29 C30 97.9(6) . . . . ? C35 C28 C29 C30 -83.5(6) . . . . ? C27 C28 C29 C34 -84.1(5) . . . . ? C35 C28 C29 C34 94.5(5) . . . . ? C34 C29 C30 F10 -179.3(5) . . . . ? C28 C29 C30 F10 -1.2(8) . . . . ? C34 C29 C30 C31 -2.0(8) . . . . ? C28 C29 C30 C31 176.0(5) . . . . ? F10 C30 C31 F9 -2.3(10) . . . . ? C29 C30 C31 F9 -179.6(6) . . . . ? F10 C30 C31 C32 178.2(6) . . . . ? C29 C30 C31 C32 0.9(10) . . . . ? F9 C31 C32 C33 -178.3(7) . . . . ? C30 C31 C32 C33 1.2(11) . . . . ? F9 C31 C32 F8 2.9(11) . . . . ? C30 C31 C32 F8 -177.5(5) . . . . ? F8 C32 C33 C34 176.6(6) . . . . ? C31 C32 C33 C34 -2.0(11) . . . . ? F8 C32 C33 F7 -0.9(11) . . . . ? C31 C32 C33 F7 -179.4(6) . . . . ? C32 C33 C34 F6 179.5(6) . . . . ? F7 C33 C34 F6 -3.2(8) . . . . ? C32 C33 C34 C29 0.7(9) . . . . ? F7 C33 C34 C29 178.1(5) . . . . ? C30 C29 C34 C33 1.3(8) . . . . ? C28 C29 C34 C33 -176.7(5) . . . . ? C30 C29 C34 F6 -177.4(5) . . . . ? C28 C29 C34 F6 4.5(7) . . . . ? C27 C28 C35 N3 1.1(7) . . . . ? C29 C28 C35 N3 -177.3(4) . . . . ? C27 C28 C35 C36 178.7(4) . . . . ? C29 C28 C35 C36 0.2(6) . . . . ? N3 C35 C36 C37 0.2(4) . . . . ? C28 C35 C36 C37 -177.6(4) . . . . ? C35 C36 C37 C38 -0.2(4) . . . . ? C35 C36 C37 C39 179.1(4) . . . . ? C36 C37 C38 N3 0.1(4) . . . . ? C39 C37 C38 N3 -179.2(4) . . . . ? C36 C37 C38 C62 179.2(4) . . . . ? C39 C37 C38 C62 -0.1(7) . . . . ? C36 C37 C39 C42 121.3(4) . . . . ? C38 C37 C39 C42 -59.5(5) . . . . ? C36 C37 C39 C41 -113.2(4) . . . . ? C38 C37 C39 C41 66.0(5) . . . . ? C36 C37 C39 C40 2.8(5) . . . . ? C38 C37 C39 C40 -178.0(4) . . . . ? C41 C39 C42 C43 18.1(5) . . . . ? C37 C39 C42 C43 141.5(4) . . . . ? C40 C39 C42 C43 -99.0(5) . . . . ? C41 C39 C42 C47 -166.1(4) . . . . ? C37 C39 C42 C47 -42.7(5) . . . . ? C40 C39 C42 C47 76.8(5) . . . . ? C47 C42 C43 C44 0.0(6) . . . . ? C39 C42 C43 C44 176.0(4) . . . . ? C42 C43 C44 C45 0.3(7) . . . . ? C43 C44 C45 C46 -0.8(6) . . . . ? C43 C44 C45 C48 -178.4(4) . . . . ? C44 C45 C46 C47 1.1(6) . . . . ? C48 C45 C46 C47 178.8(4) . . . . ? C45 C46 C47 C42 -0.9(7) . . . . ? C43 C42 C47 C46 0.3(6) . . . . ? C39 C42 C47 C46 -175.8(4) . . . . ? C44 C45 C48 C51 -135.0(5) . . . . ? C46 C45 C48 C51 47.5(6) . . . . ? C44 C45 C48 C50 -15.0(6) . . . . ? C46 C45 C48 C50 167.5(4) . . . . ? C44 C45 C48 C49 104.6(6) . . . . ? C46 C45 C48 C49 -72.9(5) . . . . ? C45 C48 C51 N4 30.0(6) . . . . ? C50 C48 C51 N4 -92.5(5) . . . . ? C49 C48 C51 N4 149.5(5) . . . . ? C45 C48 C51 C52 -157.3(5) . . . . ? C50 C48 C51 C52 80.2(6) . . . . ? C49 C48 C51 C52 -37.8(7) . . . . ? N4 C51 C52 C53 -0.8(6) . . . . ? C48 C51 C52 C53 -174.3(5) . . . . ? C51 C52 C53 C54 0.2(7) . . . . ? C8 C7 C54 N4 -1.0(7) . . . . ? C6 C7 C54 N4 178.6(4) . . . . ? C8 C7 C54 C53 -179.1(5) . . . . ? C6 C7 C54 C53 0.5(8) . . . . ? C52 C53 C54 C7 178.6(5) . . . . ? C52 C53 C54 N4 0.3(6) . . . . ? N1 C11 C55 O1 -60.6(5) . . . . ? C10 C11 C55 O1 120.7(5) . . . . ? N1 C11 C55 C56 65.5(5) . . . . ? C10 C11 C55 C56 -113.2(5) . . . . ? O1 C55 C56 C57 52.9(5) . . . . ? C11 C55 C56 C57 -69.2(5) . . . . ? O1 C55 C56 C61 -127.1(4) . . . . ? C11 C55 C56 C61 110.7(5) . . . . ? C61 C56 C57 F15 176.7(4) . . . . ? C55 C56 C57 F15 -3.3(6) . . . . ? C61 C56 C57 C58 -1.1(7) . . . . ? C55 C56 C57 C58 178.8(4) . . . . ? F15 C57 C58 F14 1.7(7) . . . . ? C56 C57 C58 F14 179.6(4) . . . . ? F15 C57 C58 C59 -179.4(5) . . . . ? C56 C57 C58 C59 -1.4(8) . . . . ? F14 C58 C59 F13 0.3(9) . . . . ? C57 C58 C59 F13 -178.7(5) . . . . ? F14 C58 C59 C60 -178.3(6) . . . . ? C57 C58 C59 C60 2.7(9) . . . . ? F13 C59 C60 F12 -1.1(11) . . . . ? C58 C59 C60 F12 177.5(5) . . . . ? F13 C59 C60 C61 179.9(5) . . . . ? C58 C59 C60 C61 -1.5(10) . . . . ? F12 C60 C61 F11 -2.5(8) . . . . ? C59 C60 C61 F11 176.5(6) . . . . ? F12 C60 C61 C56 179.8(5) . . . . ? C59 C60 C61 C56 -1.1(10) . . . . ? C57 C56 C61 F11 -175.2(4) . . . . ? C55 C56 C61 F11 4.8(7) . . . . ? C57 C56 C61 C60 2.3(7) . . . . ? C55 C56 C61 C60 -177.6(5) . . . . ? N3 C38 C62 O1 -60.1(5) . . . . ? C37 C38 C62 O1 120.9(4) . . . . ? N3 C38 C62 C63 65.1(5) . . . . ? C37 C38 C62 C63 -114.0(4) . . . . ? O1 C62 C63 C68 55.4(5) . . . . ? C38 C62 C63 C68 -66.2(5) . . . . ? O1 C62 C63 C64 -123.7(4) . . . . ? C38 C62 C63 C64 114.7(4) . . . . ? C68 C63 C64 F20 -176.6(4) . . . . ? C62 C63 C64 F20 2.7(6) . . . . ? C68 C63 C64 C65 1.8(6) . . . . ? C62 C63 C64 C65 -179.0(4) . . . . ? F20 C64 C65 F19 -2.5(7) . . . . ? C63 C64 C65 F19 179.1(4) . . . . ? F20 C64 C65 C66 178.6(4) . . . . ? C63 C64 C65 C66 0.2(7) . . . . ? F19 C65 C66 F18 -1.8(8) . . . . ? C64 C65 C66 F18 177.1(5) . . . . ? F19 C65 C66 C67 179.3(5) . . . . ? C64 C65 C66 C67 -1.7(8) . . . . ? F18 C66 C67 F17 1.8(8) . . . . ? C65 C66 C67 F17 -179.3(5) . . . . ? F18 C66 C67 C68 -177.6(5) . . . . ? C65 C66 C67 C68 1.3(8) . . . . ? C64 C63 C68 F16 176.1(4) . . . . ? C62 C63 C68 F16 -3.1(6) . . . . ? C64 C63 C68 C67 -2.3(6) . . . . ? C62 C63 C68 C67 178.5(4) . . . . ? F17 C67 C68 F16 3.0(6) . . . . ? C66 C67 C68 F16 -177.6(4) . . . . ? F17 C67 C68 C63 -178.6(4) . . . . ? C66 C67 C68 C63 0.9(7) . . . . ? C10 C11 N1 C8 0.1(5) . . . . ? C55 C11 N1 C8 -178.9(4) . . . . ? C7 C8 N1 C11 -179.4(4) . . . . ? C9 C8 N1 C11 0.1(5) . . . . ? C25 C24 N2 C27 0.7(6) . . . . ? C21 C24 N2 C27 174.2(5) . . . . ? C28 C27 N2 C24 178.9(5) . . . . ? C26 C27 N2 C24 -1.2(6) . . . . ? C37 C38 N3 C35 0.1(4) . . . . ? C62 C38 N3 C35 -179.2(3) . . . . ? C36 C35 N3 C38 -0.2(4) . . . . ? C28 C35 N3 C38 177.8(4) . . . . ? C52 C51 N4 C54 1.0(5) . . . . ? C48 C51 N4 C54 174.8(4) . . . . ? C7 C54 N4 C51 -179.3(4) . . . . ? C53 C54 N4 C51 -0.8(5) . . . . ? C11 C55 O1 C62 164.9(3) . . . . ? C56 C55 O1 C62 40.4(5) . . . . ? C38 C62 O1 C55 164.5(3) . . . . ? C63 C62 O1 C55 40.0(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1A F15 0.899(12) 2.14(5) 2.783(4) 128(5) . N1 H1A N4 0.899(12) 2.15(5) 2.794(5) 128(5) . N3 H3A F16 0.896(12) 2.16(5) 2.751(4) 122(5) . _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 22.53 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.470 _refine_diff_density_min -0.392 _refine_diff_density_rms 0.062 _vrf_THETM01_I ; PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550 RESPONSE: The crystal was poorly diffracting at higher bgagg angles. The situation did not improve even after re-crystallisation and frash data collection. ; _vrf_PLAT023_I ; PROBLEM: Resolution (too) Low [sin(theta)/Lambda < 0.6].. 22.53 Deg. RESPONSE: The crystal was poorly diffracting at higher bgagg angles. The situation did not improve even after re-crystallisation and frash data collection. ; # end Validation Reply Form _database_code_depnum_ccdc_archive 'CCDC 926222'