# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Prof Francois Diederich' _publ_contact_author_email DIEDERICH@ORG.CHEM.ETHZ.CH _publ_section_title ; Substituent effects on the aromatic edge-to-face interaction ; loop_ _publ_author_name 'Francois Diederich ' 'Felix Raoul Fischer' 'W.Bernd Schweizer' # Attachment '_R,R_-4.cif' # CIF Copied by cif2cif, version 0.0.8 - beta ( 2 Apr 98) data_1 _database_code_depnum_ccdc_archive 'CCDC 688768' _chemical_compound_source 'Diederich laboratory' _exptl_crystal_description Cube _exptl_crystal_size_max .2 _exptl_crystal_size_mid .18 _exptl_crystal_size_min .08 _exptl_crystal_F_000 1160.0 _exptl_crystal_colour Colourless _cell_measurement_temperature 223 _refine_ls_hydrogen_treatment refall _diffrn_measurement_device KappaCCD _computing_data_collection KappaCCD _computing_data_reduction 'Denzo and Scalepak (Otwinowski & Minor, 1997)' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 25 loop_ _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_wavelength_id all _diffrn_orient_matrix_type X=UH _diffrn_orient_matrix_UB_11 0.01623 _diffrn_orient_matrix_UB_12 0.09573 _diffrn_orient_matrix_UB_13 0.01032 _diffrn_orient_matrix_UB_21 -0.00187 _diffrn_orient_matrix_UB_22 0.00890 _diffrn_orient_matrix_UB_23 -0.07960 _diffrn_orient_matrix_UB_31 -0.04694 _diffrn_orient_matrix_UB_32 0.01420 _diffrn_orient_matrix_UB_33 0.00269 _cell_formula_units_Z 4 _exptl_crystal_density_diffrn 1.411 _exptl_crystal_density_method 'not measured' _exptl_special_details ; ? ; _chemical_formula_weight 557.572 _diffrn_radiation_type ' MoK\a' loop_ _symmetry_equiv_pos_as_xyz +X,+Y,+Z -X,-Y,-Z '-X+ 1/2,+Y+ 1/2,-Z+ 1/2' '+X+ 1/2,-Y+ 1/2,+Z+ 1/2' _symmetry_space_group_name_H-M 'P 21/n ' _symmetry_cell_setting Monoclinic _chemical_formula_moiety 'C32 H26 F3 N3 O3 ' _chemical_formula_sum 'C32 H26 F3 N3 O3 ' _chemical_name_systematic ; ? ; _cell_length_a 10.3299(3) _cell_length_b 12.4818(4) _cell_length_c 20.5365(7) _cell_angle_alpha 90.00 _cell_angle_beta 97.4946(12) _cell_angle_gamma 90.00 _cell_volume 2625.27(14) _diffrn_reflns_number 9643 _diffrn_reflns_theta_max 27.45 _diffrn_reflns_theta_min 2.85 _diffrn_reflns_theta_full 27.45 _cell_measurement_reflns_used 15319 _cell_measurement_theta_min 2.753 _cell_measurement_theta_max 27.485 _diffrn_measurement_method CCD _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SIR97(Altomare et al., J. Appl. Cryst.,1999)' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? 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' 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' _exptl_absorpt_coefficient_mu 0.106 _reflns_number_total 5891 _reflns_number_gt 3839 _reflns_threshold_expression >2sigma(I) _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+ (0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5891 _refine_ls_number_parameters 474 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0980 _refine_ls_R_factor_gt 0.0568 _refine_ls_wR_factor_ref 0.1730 _refine_ls_wR_factor_gt 0.1440 _refine_ls_goodness_of_fit_ref 0.992 _refine_ls_restrained_S_all 0.992 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.001 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 F39 F -0.15885(16) 0.11174(15) 1.10493(7) 0.0627(5) Uani 1 1 d . . . F40 F -0.25094(19) 0.25978(14) 1.07398(8) 0.0679(5) Uani 1 1 d . . . F41 F -0.36530(16) 0.11776(15) 1.07713(8) 0.0635(5) Uani 1 1 d . . . O20 O -0.0180(2) 0.42242(17) 1.06766(10) 0.0657(6) Uani 1 1 d . . . O30 O -0.1794(2) -0.09931(15) 0.81064(9) 0.0564(5) Uani 1 1 d . . . O31 O -0.18929(17) 0.07877(13) 0.79677(8) 0.0442(4) Uani 1 1 d . . . N5 N 0.24193(18) 0.34840(16) 0.80718(9) 0.0344(4) Uani 1 1 d . . . N13 N 0.36202(17) 0.20330(16) 0.86627(9) 0.0346(4) Uani 1 1 d . . . N18 N 0.10935(19) 0.27505(17) 1.08997(10) 0.0388(5) Uani 1 1 d . . . C1 C -0.0151(2) 0.12267(17) 0.70390(10) 0.0311(5) Uani 1 1 d . . . C2 C -0.0420(2) 0.23263(18) 0.70041(11) 0.0358(5) Uani 1 1 d . . . C3 C 0.0432(2) 0.30473(18) 0.73408(11) 0.0354(5) Uani 1 1 d . . . C4 C 0.1561(2) 0.26975(17) 0.77313(10) 0.0298(5) Uani 1 1 d . . . C6 C 0.1913(2) 0.39042(19) 0.86598(11) 0.0361(5) Uani 1 1 d . . . C7 C 0.2095(2) 0.31215(18) 0.92269(10) 0.0316(5) Uani 1 1 d . . . C8 C 0.1475(2) 0.33110(18) 0.97819(11) 0.0333(5) Uani 1 1 d . . . C9 C 0.1636(2) 0.25970(18) 1.03072(10) 0.0330(5) Uani 1 1 d . . . C10 C 0.2377(2) 0.16699(19) 1.02660(11) 0.0356(5) Uani 1 1 d . . . C11 C 0.3002(2) 0.14864(19) 0.97205(11) 0.0351(5) Uani 1 1 d . . . C12 C 0.2885(2) 0.22224(18) 0.92025(10) 0.0320(5) Uani 1 1 d . . . C14 C 0.3027(2) 0.11939(19) 0.82098(11) 0.0342(5) Uani 1 1 d . . . C15 C 0.1837(2) 0.16051(17) 0.77736(10) 0.0304(5) Uani 1 1 d . . . C16 C 0.0975(2) 0.08836(18) 0.74217(11) 0.0313(5) Uani 1 1 d . . . C17 C 0.3704(2) 0.3016(2) 0.82827(12) 0.0379(5) Uani 1 1 d . . . C19 C 0.0282(2) 0.3544(2) 1.10578(12) 0.0433(6) Uani 1 1 d . . . C21 C 0.0011(4) 0.3507(3) 1.17623(15) 0.0557(7) Uani 1 1 d . . . C22 C -0.1069(2) 0.04276(17) 0.66818(11) 0.0311(5) Uani 1 1 d . . . C23 C -0.1173(2) 0.03468(17) 0.59951(11) 0.0333(5) Uani 1 1 d . . . C24 C -0.2016(2) -0.0416(2) 0.56770(12) 0.0412(6) Uani 1 1 d . . . C25 C -0.2715(3) -0.1114(2) 0.60231(14) 0.0453(6) Uani 1 1 d . . . C26 C -0.2581(2) -0.1068(2) 0.66962(13) 0.0410(5) Uani 1 1 d . . . C27 C -0.1786(2) -0.02800(18) 0.70272(11) 0.0354(5) Uani 1 1 d . . . C28 C -0.0369(3) 0.1042(2) 0.56081(13) 0.0424(6) Uani 1 1 d . . . C29 C -0.1790(2) -0.02335(19) 0.77488(11) 0.0364(5) Uani 1 1 d . . . C32 C -0.2020(2) 0.09272(18) 0.86361(11) 0.0360(5) Uani 1 1 d . . . C33 C -0.0939(2) 0.0935(2) 0.91024(13) 0.0414(6) Uani 1 1 d . . . C34 C -0.1104(2) 0.1122(2) 0.97502(12) 0.0395(5) Uani 1 1 d . . . C35 C -0.2337(2) 0.13122(18) 0.99199(11) 0.0353(5) Uani 1 1 d . . . C36 C -0.3417(2) 0.1317(2) 0.94386(12) 0.0420(6) Uani 1 1 d . . . C37 C -0.3255(2) 0.1119(2) 0.87940(13) 0.0443(6) Uani 1 1 d . . . C38 C -0.2519(3) 0.1545(2) 1.06160(13) 0.0455(6) Uani 1 1 d . . . H8 H 0.094(2) 0.398(2) 0.9799(12) 0.037(6) Uiso 1 1 d . . . H34 H -0.038(2) 0.115(2) 1.0084(13) 0.041(7) Uiso 1 1 d . . . H10 H 0.249(2) 0.116(2) 1.0632(13) 0.037(6) Uiso 1 1 d . . . H2 H -0.123(3) 0.258(2) 0.6743(13) 0.045(7) Uiso 1 1 d . . . H17A H 0.424(2) 0.354(2) 0.8559(12) 0.041(7) Uiso 1 1 d . . . H24 H -0.210(3) -0.048(3) 0.5211(15) 0.057(8) Uiso 1 1 d . . . H16 H 0.113(2) 0.014(2) 0.7468(12) 0.040(6) Uiso 1 1 d . . . H6A H 0.235(3) 0.458(2) 0.8773(14) 0.052(8) Uiso 1 1 d . . . H14A H 0.367(3) 0.093(2) 0.7935(14) 0.046(7) Uiso 1 1 d . . . H3 H 0.024(2) 0.383(2) 0.7324(12) 0.037(6) Uiso 1 1 d . . . H17B H 0.413(2) 0.284(2) 0.7893(13) 0.041(7) Uiso 1 1 d . . . H6B H 0.095(3) 0.408(2) 0.8561(13) 0.047(7) Uiso 1 1 d . . . H11 H 0.354(2) 0.084(2) 0.9702(12) 0.042(7) Uiso 1 1 d . . . H33 H -0.014(3) 0.080(2) 0.8963(14) 0.051(8) Uiso 1 1 d . . . H18 H 0.132(3) 0.227(2) 1.1182(15) 0.052(8) Uiso 1 1 d . . . H25 H -0.326(3) -0.162(2) 0.5772(14) 0.055(8) Uiso 1 1 d . . . H14B H 0.279(3) 0.059(2) 0.8460(13) 0.047(7) Uiso 1 1 d . . . H36 H -0.427(3) 0.149(2) 0.9557(13) 0.053(8) Uiso 1 1 d . . . H26 H -0.309(3) -0.156(2) 0.6947(14) 0.055(8) Uiso 1 1 d . . . H37 H -0.398(3) 0.117(2) 0.8467(13) 0.046(7) Uiso 1 1 d . . . H28A H -0.050(3) 0.088(3) 0.5146(17) 0.065(9) Uiso 1 1 d . . . H28B H 0.055(3) 0.094(3) 0.5726(16) 0.069(9) Uiso 1 1 d . . . H28C H -0.049(3) 0.179(3) 0.5659(17) 0.076(10) Uiso 1 1 d . . . H21A H 0.044(4) 0.290(3) 1.200(2) 0.093(12) Uiso 1 1 d . . . H21B H -0.088(5) 0.347(4) 1.177(2) 0.108(14) Uiso 1 1 d . . . H21C H 0.029(5) 0.413(4) 1.196(3) 0.130(18) 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 F39 0.0700(11) 0.0779(12) 0.0380(9) 0.0044(8) -0.0009(7) 0.0122(9) F40 0.0994(14) 0.0469(10) 0.0583(11) -0.0145(8) 0.0133(9) 0.0029(9) F41 0.0629(10) 0.0825(13) 0.0499(10) -0.0063(8) 0.0257(7) -0.0068(9) O20 0.0911(15) 0.0569(13) 0.0561(12) 0.0184(10) 0.0358(11) 0.0286(11) O30 0.0912(15) 0.0370(10) 0.0402(10) 0.0078(8) 0.0051(9) -0.0055(9) O31 0.0622(11) 0.0368(9) 0.0356(9) 0.0032(7) 0.0140(7) 0.0025(8) N5 0.0404(10) 0.0380(10) 0.0258(9) -0.0009(8) 0.0082(7) -0.0083(8) N13 0.0304(9) 0.0423(11) 0.0308(10) -0.0039(8) 0.0031(7) -0.0027(8) N18 0.0458(11) 0.0399(11) 0.0320(11) 0.0039(9) 0.0102(8) 0.0021(9) C1 0.0345(11) 0.0313(11) 0.0279(11) -0.0002(9) 0.0050(8) -0.0017(9) C2 0.0392(12) 0.0329(12) 0.0341(12) 0.0031(10) 0.0002(9) 0.0044(9) C3 0.0435(12) 0.0283(11) 0.0342(12) 0.0003(9) 0.0047(9) 0.0012(9) C4 0.0361(11) 0.0301(11) 0.0240(10) 0.0005(8) 0.0066(8) -0.0020(8) C6 0.0472(13) 0.0323(12) 0.0293(12) -0.0007(9) 0.0066(9) -0.0040(10) C7 0.0314(10) 0.0346(12) 0.0284(11) -0.0013(9) 0.0021(8) -0.0042(9) C8 0.0352(11) 0.0321(12) 0.0326(12) -0.0038(9) 0.0042(8) -0.0028(9) C9 0.0341(11) 0.0375(12) 0.0276(11) -0.0020(9) 0.0046(8) -0.0050(9) C10 0.0389(12) 0.0369(12) 0.0307(12) 0.0037(10) 0.0032(9) -0.0033(9) C11 0.0342(11) 0.0340(12) 0.0366(12) 0.0003(10) 0.0031(9) 0.0009(9) C12 0.0298(10) 0.0356(12) 0.0299(11) -0.0048(9) 0.0020(8) -0.0050(8) C14 0.0345(11) 0.0365(12) 0.0312(12) -0.0038(10) 0.0026(9) 0.0049(9) C15 0.0326(10) 0.0328(11) 0.0262(11) -0.0011(9) 0.0055(8) 0.0014(8) C16 0.0349(11) 0.0302(12) 0.0292(11) 0.0011(9) 0.0054(8) 0.0024(9) C17 0.0356(12) 0.0448(14) 0.0340(13) -0.0021(11) 0.0070(9) -0.0091(10) C19 0.0521(14) 0.0414(14) 0.0394(14) 0.0046(11) 0.0168(11) 0.0012(11) C21 0.071(2) 0.062(2) 0.0384(15) 0.0007(14) 0.0210(14) 0.0058(16) C22 0.0324(11) 0.0275(11) 0.0329(11) -0.0005(9) 0.0018(8) 0.0042(8) C23 0.0359(11) 0.0303(11) 0.0329(12) -0.0011(9) 0.0018(8) 0.0046(9) C24 0.0479(13) 0.0404(14) 0.0330(13) -0.0055(10) -0.0032(10) 0.0041(11) C25 0.0469(14) 0.0378(13) 0.0488(15) -0.0087(12) -0.0027(11) -0.0045(11) C26 0.0439(13) 0.0354(12) 0.0437(14) -0.0023(11) 0.0052(10) -0.0052(10) C27 0.0373(11) 0.0321(12) 0.0361(12) 0.0009(10) 0.0027(9) 0.0019(9) C28 0.0459(14) 0.0451(15) 0.0370(14) 0.0023(11) 0.0082(10) 0.0019(11) C29 0.0380(12) 0.0339(12) 0.0365(12) 0.0024(10) 0.0022(9) -0.0029(9) C32 0.0436(12) 0.0319(12) 0.0331(12) 0.0038(9) 0.0077(9) -0.0005(9) C33 0.0314(12) 0.0462(14) 0.0480(14) 0.0012(11) 0.0110(10) 0.0025(10) C34 0.0323(11) 0.0434(13) 0.0409(13) 0.0001(11) -0.0027(9) -0.0007(10) C35 0.0376(11) 0.0325(12) 0.0360(12) 0.0029(10) 0.0056(9) 0.0008(9) C36 0.0302(11) 0.0541(15) 0.0426(14) 0.0027(12) 0.0080(9) 0.0043(10) C37 0.0352(12) 0.0565(16) 0.0396(14) 0.0007(12) -0.0011(10) 0.0019(11) C38 0.0502(14) 0.0437(14) 0.0429(14) -0.0025(12) 0.0070(11) 0.0018(11) _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 F39 C38 1.333(3) . ? F40 C38 1.338(3) . ? F41 C38 1.335(3) . ? O20 C19 1.210(3) . ? O30 C29 1.200(3) . ? O31 C29 1.360(3) . ? O31 C32 1.407(3) . ? N5 C4 1.441(3) . ? N5 C17 1.463(3) . ? N5 C6 1.473(3) . ? N13 C12 1.443(3) . ? N13 C17 1.462(3) . ? N13 C14 1.479(3) . ? N18 C19 1.364(3) . ? N18 C9 1.417(3) . ? C1 C16 1.384(3) . ? C1 C2 1.400(3) . ? C1 C22 1.500(3) . ? C2 C3 1.380(3) . ? C3 C4 1.397(3) . ? C4 C15 1.393(3) . ? C6 C7 1.513(3) . ? C7 C12 1.392(3) . ? C7 C8 1.399(3) . ? C8 C9 1.392(3) . ? C9 C10 1.396(3) . ? C10 C11 1.382(3) . ? C11 C12 1.399(3) . ? C14 C15 1.514(3) . ? C15 C16 1.399(3) . ? C19 C21 1.510(4) . ? C22 C27 1.403(3) . ? C22 C23 1.404(3) . ? C23 C24 1.395(3) . ? C23 C28 1.499(3) . ? C24 C25 1.385(4) . ? C25 C26 1.372(4) . ? C26 C27 1.399(3) . ? C27 C29 1.484(3) . ? C32 C33 1.373(3) . ? C32 C37 1.377(3) . ? C33 C34 1.383(4) . ? C34 C35 1.384(3) . ? C35 C36 1.391(3) . ? C35 C38 1.494(3) . ? C36 C37 1.378(3) . ? N18 H18 0.84(3) . ? C2 H2 0.99(3) . ? C3 H3 0.99(3) . ? C6 H6A 0.97(3) . ? C6 H6B 1.01(3) . ? C8 H8 1.00(3) . ? C10 H10 0.98(3) . ? C11 H11 0.99(3) . ? C14 H14A 0.98(3) . ? C14 H14B 0.96(3) . ? C16 H16 0.94(3) . ? C17 H17A 0.99(3) . ? C17 H17B 0.99(3) . ? C21 H21A 0.97(4) . ? C21 H21B 0.92(5) . ? C21 H21C 0.90(6) . ? C24 H24 0.95(3) . ? C25 H25 0.95(3) . ? C26 H26 0.99(3) . ? C28 H28A 0.96(3) . ? C28 H28B 0.96(3) . ? C28 H28C 0.95(4) . ? C33 H33 0.92(3) . ? C34 H34 0.95(3) . ? C36 H36 0.97(3) . ? C37 H37 0.94(3) . ? 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 C29 O31 C32 117.37(18) . . ? C4 N5 C17 110.38(18) . . ? C4 N5 C6 112.25(17) . . ? C17 N5 C6 107.74(18) . . ? C12 N13 C17 110.28(18) . . ? C12 N13 C14 112.51(17) . . ? C17 N13 C14 107.86(18) . . ? C19 N18 C9 128.8(2) . . ? C16 C1 C2 118.6(2) . . ? C16 C1 C22 120.18(19) . . ? C2 C1 C22 121.21(19) . . ? C3 C2 C1 120.3(2) . . ? C2 C3 C4 120.9(2) . . ? C15 C4 C3 119.36(19) . . ? C15 C4 N5 121.91(19) . . ? C3 C4 N5 118.72(19) . . ? N5 C6 C7 112.29(19) . . ? C12 C7 C8 119.9(2) . . ? C12 C7 C6 120.49(19) . . ? C8 C7 C6 119.6(2) . . ? C9 C8 C7 120.1(2) . . ? C8 C9 C10 119.6(2) . . ? C8 C9 N18 123.9(2) . . ? C10 C9 N18 116.4(2) . . ? C11 C10 C9 120.3(2) . . ? C10 C11 C12 120.3(2) . . ? C7 C12 C11 119.7(2) . . ? C7 C12 N13 121.96(19) . . ? C11 C12 N13 118.4(2) . . ? N13 C14 C15 111.70(18) . . ? C4 C15 C16 119.11(19) . . ? C4 C15 C14 120.82(19) . . ? C16 C15 C14 120.0(2) . . ? C1 C16 C15 121.7(2) . . ? N13 C17 N5 112.24(18) . . ? O20 C19 N18 123.9(2) . . ? O20 C19 C21 122.3(2) . . ? N18 C19 C21 113.8(2) . . ? C27 C22 C23 119.1(2) . . ? C27 C22 C1 120.9(2) . . ? C23 C22 C1 119.95(19) . . ? C24 C23 C22 118.7(2) . . ? C24 C23 C28 120.2(2) . . ? C22 C23 C28 121.1(2) . . ? C25 C24 C23 121.6(2) . . ? C26 C25 C24 120.0(2) . . ? C25 C26 C27 119.7(2) . . ? C26 C27 C22 120.8(2) . . ? C26 C27 C29 115.8(2) . . ? C22 C27 C29 123.4(2) . . ? O30 C29 O31 122.1(2) . . ? O30 C29 C27 125.5(2) . . ? O31 C29 C27 112.16(19) . . ? C33 C32 C37 121.9(2) . . ? C33 C32 O31 120.7(2) . . ? C37 C32 O31 117.3(2) . . ? C32 C33 C34 118.7(2) . . ? C33 C34 C35 120.3(2) . . ? C34 C35 C36 120.1(2) . . ? C34 C35 C38 120.6(2) . . ? C36 C35 C38 119.3(2) . . ? C37 C36 C35 119.7(2) . . ? C32 C37 C36 119.3(2) . . ? F39 C38 F41 106.4(2) . . ? F39 C38 F40 106.2(2) . . ? F41 C38 F40 106.0(2) . . ? F39 C38 C35 113.0(2) . . ? F41 C38 C35 112.7(2) . . ? F40 C38 C35 112.0(2) . . ? C19 N18 H18 118(2) . . ? C9 N18 H18 113(2) . . ? C3 C2 H2 120.5(16) . . ? C1 C2 H2 119.2(16) . . ? C2 C3 H3 120.7(14) . . ? C4 C3 H3 118.4(14) . . ? N5 C6 H6A 107.5(16) . . ? C7 C6 H6A 111.7(17) . . ? N5 C6 H6B 110.9(15) . . ? C7 C6 H6B 108.4(15) . . ? H6A C6 H6B 106(2) . . ? C9 C8 H8 121.0(14) . . ? C7 C8 H8 118.9(14) . . ? C11 C10 H10 119.5(15) . . ? C9 C10 H10 120.2(15) . . ? C10 C11 H11 119.5(15) . . ? C12 C11 H11 120.2(15) . . ? N13 C14 H14A 109.9(16) . . ? C15 C14 H14A 109.2(16) . . ? N13 C14 H14B 109.6(16) . . ? C15 C14 H14B 109.8(16) . . ? H14A C14 H14B 106(2) . . ? C1 C16 H16 118.5(16) . . ? C15 C16 H16 119.7(16) . . ? N13 C17 H17A 108.6(15) . . ? N5 C17 H17A 108.8(15) . . ? N13 C17 H17B 108.2(15) . . ? N5 C17 H17B 109.4(14) . . ? H17A C17 H17B 110(2) . . ? C19 C21 H21A 112(2) . . ? C19 C21 H21B 110(3) . . ? H21A C21 H21B 110(4) . . ? C19 C21 H21C 108(3) . . ? H21A C21 H21C 110(4) . . ? H21B C21 H21C 107(4) . . ? C25 C24 H24 118.3(19) . . ? C23 C24 H24 120.0(19) . . ? C26 C25 H25 123.4(18) . . ? C24 C25 H25 116.6(18) . . ? C25 C26 H26 120.5(17) . . ? C27 C26 H26 119.8(17) . . ? C23 C28 H28A 112.4(19) . . ? C23 C28 H28B 112.6(19) . . ? H28A C28 H28B 103(3) . . ? C23 C28 H28C 115(2) . . ? H28A C28 H28C 108(3) . . ? H28B C28 H28C 104(3) . . ? C32 C33 H33 117.5(17) . . ? C34 C33 H33 123.8(17) . . ? C33 C34 H34 121.3(15) . . ? C35 C34 H34 118.5(15) . . ? C37 C36 H36 120.6(16) . . ? C35 C36 H36 119.6(16) . . ? C32 C37 H37 121.2(16) . . ? C36 C37 H37 119.3(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 C16 C1 C2 C3 0.6(3) . . . . ? C22 C1 C2 C3 179.4(2) . . . . ? C1 C2 C3 C4 -1.2(3) . . . . ? C2 C3 C4 C15 0.8(3) . . . . ? C2 C3 C4 N5 179.88(19) . . . . ? C17 N5 C4 C15 16.3(3) . . . . ? C6 N5 C4 C15 -103.9(2) . . . . ? C17 N5 C4 C3 -162.71(19) . . . . ? C6 N5 C4 C3 77.1(2) . . . . ? C4 N5 C6 C7 76.3(2) . . . . ? C17 N5 C6 C7 -45.5(2) . . . . ? N5 C6 C7 C12 11.6(3) . . . . ? N5 C6 C7 C8 -169.04(19) . . . . ? C12 C7 C8 C9 -0.6(3) . . . . ? C6 C7 C8 C9 -179.9(2) . . . . ? C7 C8 C9 C10 -2.6(3) . . . . ? C7 C8 C9 N18 177.0(2) . . . . ? C19 N18 C9 C8 4.3(4) . . . . ? C19 N18 C9 C10 -176.1(2) . . . . ? C8 C9 C10 C11 3.2(3) . . . . ? N18 C9 C10 C11 -176.4(2) . . . . ? C9 C10 C11 C12 -0.6(3) . . . . ? C8 C7 C12 C11 3.1(3) . . . . ? C6 C7 C12 C11 -177.6(2) . . . . ? C8 C7 C12 N13 -175.43(18) . . . . ? C6 C7 C12 N13 3.9(3) . . . . ? C10 C11 C12 C7 -2.5(3) . . . . ? C10 C11 C12 N13 176.07(19) . . . . ? C17 N13 C12 C7 16.1(3) . . . . ? C14 N13 C12 C7 -104.3(2) . . . . ? C17 N13 C12 C11 -162.42(19) . . . . ? C14 N13 C12 C11 77.1(2) . . . . ? C12 N13 C14 C15 75.8(2) . . . . ? C17 N13 C14 C15 -46.1(2) . . . . ? C3 C4 C15 C16 0.2(3) . . . . ? N5 C4 C15 C16 -178.88(18) . . . . ? C3 C4 C15 C14 -177.94(19) . . . . ? N5 C4 C15 C14 3.0(3) . . . . ? N13 C14 C15 C4 12.6(3) . . . . ? N13 C14 C15 C16 -165.47(19) . . . . ? C2 C1 C16 C15 0.4(3) . . . . ? C22 C1 C16 C15 -178.47(19) . . . . ? C4 C15 C16 C1 -0.7(3) . . . . ? C14 C15 C16 C1 177.4(2) . . . . ? C12 N13 C17 N5 -53.4(2) . . . . ? C14 N13 C17 N5 69.8(2) . . . . ? C4 N5 C17 N13 -53.2(2) . . . . ? C6 N5 C17 N13 69.7(2) . . . . ? C9 N18 C19 O20 5.3(4) . . . . ? C9 N18 C19 C21 -174.2(2) . . . . ? C16 C1 C22 C27 67.8(3) . . . . ? C2 C1 C22 C27 -111.0(3) . . . . ? C16 C1 C22 C23 -109.1(2) . . . . ? C2 C1 C22 C23 72.1(3) . . . . ? C27 C22 C23 C24 1.8(3) . . . . ? C1 C22 C23 C24 178.8(2) . . . . ? C27 C22 C23 C28 -176.5(2) . . . . ? C1 C22 C23 C28 0.5(3) . . . . ? C22 C23 C24 C25 -2.1(3) . . . . ? C28 C23 C24 C25 176.2(2) . . . . ? C23 C24 C25 C26 -0.3(4) . . . . ? C24 C25 C26 C27 3.1(4) . . . . ? C25 C26 C27 C22 -3.4(4) . . . . ? C25 C26 C27 C29 175.0(2) . . . . ? C23 C22 C27 C26 0.9(3) . . . . ? C1 C22 C27 C26 -176.1(2) . . . . ? C23 C22 C27 C29 -177.3(2) . . . . ? C1 C22 C27 C29 5.7(3) . . . . ? C32 O31 C29 O30 -0.7(3) . . . . ? C32 O31 C29 C27 174.65(18) . . . . ? C26 C27 C29 O30 40.2(3) . . . . ? C22 C27 C29 O30 -141.4(3) . . . . ? C26 C27 C29 O31 -134.9(2) . . . . ? C22 C27 C29 O31 43.4(3) . . . . ? C29 O31 C32 C33 83.3(3) . . . . ? C29 O31 C32 C37 -100.5(3) . . . . ? C37 C32 C33 C34 1.2(4) . . . . ? O31 C32 C33 C34 177.1(2) . . . . ? C32 C33 C34 C35 -0.9(4) . . . . ? C33 C34 C35 C36 -0.1(4) . . . . ? C33 C34 C35 C38 -178.3(2) . . . . ? C34 C35 C36 C37 0.8(4) . . . . ? C38 C35 C36 C37 179.1(2) . . . . ? C33 C32 C37 C36 -0.5(4) . . . . ? O31 C32 C37 C36 -176.6(2) . . . . ? C35 C36 C37 C32 -0.5(4) . . . . ? C34 C35 C38 F39 -26.9(3) . . . . ? C36 C35 C38 F39 154.8(2) . . . . ? C34 C35 C38 F41 -147.6(2) . . . . ? C36 C35 C38 F41 34.2(3) . . . . ? C34 C35 C38 F40 93.0(3) . . . . ? C36 C35 C38 F40 -85.2(3) . . . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.196 _refine_diff_density_min -0.275 _refine_diff_density_rms 0.054 _publ_section_references ; Mackay, S., Gilmore, C. J.,Edwards, C., Stewart, N. & Shankland, K. (1999). maXus Computer Program for the Solution and Refinement of Crystal Structures. Bruker Nonius, The Netherlands, MacScience, Japan & The University of Glasgow. Johnson, C. K. (1976). ORTEP-II. A Fortran Thermal-Ellipsoid Plot Program. Report ORNL-5138. Oak Ridge National Laboratory, Oak Ridge, Tennessee, USA. Otwinowski, Z. and Minor, W, (1997). In Methods in Enzymology, 276, edited by C.W. Carter, Jr. & R.M. Sweet pp. 307-326, New York:Academic Press. Altomare, A., Burla, M.C., Camalli, M., Cascarano, G.L., Giacovazzo, C., Guagliardi, A., Moliterni, A.G.G & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119. Sheldrick, G. M. (1997). SHELXL97. Program for the Refinement of Crystal Structures. University of G\"ottingen, Germany. ;