# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Seth M. Cohen' _publ_contact_author_email SCOHEN@UCSD.EDU _publ_section_title ; Hydrogen-Bond Rigidified BODIPY Dyes ; loop_ _publ_author_name 'Seth Cohen' 'Jennifer A. Jacobsen' 'Douglas Magde' 'Jay Stork' # Attachment '4c.cif' data_4c _database_code_depnum_ccdc_archive 'CCDC 724399' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common BODIPY(Ph,Tol) _chemical_melting_point ? _chemical_formula_moiety 'C31 H25 B F2 N4 O2, C3 H6 O' _chemical_formula_sum 'C34 H31 B F2 N4 O3' _chemical_formula_weight 592.44 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' B B 0.0013 0.0007 '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 'P 2(1)/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 11.750(3) _cell_length_b 9.834(3) _cell_length_c 25.870(7) _cell_angle_alpha 90.00 _cell_angle_beta 97.836(3) _cell_angle_gamma 90.00 _cell_volume 2961.3(14) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5661 _cell_measurement_theta_min 2.22 _cell_measurement_theta_max 23.6 _exptl_crystal_description needle _exptl_crystal_colour red _exptl_crystal_size_max 0.49 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.329 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1240 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9553 _exptl_absorpt_correction_T_max 0.9870 _exptl_absorpt_process_details 'SADABS 2.10 (Sheldrick, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 Apex' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 8.3 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 30660 _diffrn_reflns_av_R_equivalents 0.0890 _diffrn_reflns_av_sigmaI/netI 0.0815 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 1.59 _diffrn_reflns_theta_max 25.35 _reflns_number_total 5421 _reflns_number_gt 3110 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Apex2 v.1.0-2.1 (Bruker, 2006)' _computing_cell_refinement SAINT _computing_data_reduction 'SAINT v7.34A (Bruker, 2007)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL 5.1 (Sheldrick, 1994)' _computing_publication_material SHELXL97 _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. The positions of atoms H1 and H4, associated with the amide N atoms, were allowed to refine. All other H atoms were located in a difference map, placed in calculated positions, and treated with a riding model. ; _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^)+(0.0779P)^2^+8.6616P] 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 5421 _refine_ls_number_parameters 407 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1523 _refine_ls_R_factor_gt 0.0888 _refine_ls_wR_factor_ref 0.2460 _refine_ls_wR_factor_gt 0.2136 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.059 _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 B1 B 1.0085(5) 0.3201(5) 0.0517(2) 0.0314(13) Uani 1 1 d . . . C1 C 0.9127(4) 0.1557(5) -0.0208(2) 0.0406(13) Uani 1 1 d . . . C2 C 0.9459(4) 0.0939(6) -0.0652(2) 0.0463(14) Uani 1 1 d . . . H2 H 0.9034 0.0278 -0.0866 0.056 Uiso 1 1 calc R . . C3 C 1.0499(5) 0.1457(5) -0.0721(2) 0.0456(14) Uani 1 1 d . . . H3 H 1.0930 0.1226 -0.0994 0.055 Uiso 1 1 calc R . . C4 C 1.0825(4) 0.2391(5) -0.03188(19) 0.0364(12) Uani 1 1 d . . . C5 C 1.1843(4) 0.3131(5) -0.02013(18) 0.0337(12) Uani 1 1 d . . . C6 C 1.2033(4) 0.3913(5) 0.02551(19) 0.0345(12) Uani 1 1 d . . . C7 C 1.2909(4) 0.4849(5) 0.04178(19) 0.0380(12) Uani 1 1 d . . . H7 H 1.3569 0.5017 0.0252 0.046 Uiso 1 1 calc R . . C8 C 1.2643(4) 0.5474(6) 0.0856(2) 0.0436(13) Uani 1 1 d . . . H8 H 1.3080 0.6162 0.1050 0.052 Uiso 1 1 calc R . . C9 C 1.1613(4) 0.4917(5) 0.09678(19) 0.0391(12) Uani 1 1 d . . . C10 C 0.8038(4) 0.1192(5) -0.0016(2) 0.0423(13) Uani 1 1 d . . . C11 C 0.6586(4) 0.1997(5) 0.05272(17) 0.0333(12) Uani 1 1 d . . . C12 C 0.5910(4) 0.0823(5) 0.05207(19) 0.0409(13) Uani 1 1 d . . . H12 H 0.6117 0.0034 0.0343 0.049 Uiso 1 1 calc R . . C13 C 0.4953(4) 0.0805(5) 0.07676(19) 0.0413(13) Uani 1 1 d . . . H13 H 0.4509 -0.0005 0.0756 0.050 Uiso 1 1 calc R . . C14 C 0.4604(4) 0.1916(5) 0.10330(18) 0.0375(12) Uani 1 1 d . . . C15 C 0.5294(4) 0.3072(5) 0.10413(18) 0.0388(13) Uani 1 1 d . . . H15 H 0.5086 0.3856 0.1222 0.047 Uiso 1 1 calc R . . C16 C 0.6252(4) 0.3122(5) 0.08019(18) 0.0352(12) Uani 1 1 d . . . H16 H 0.6700 0.3929 0.0821 0.042 Uiso 1 1 calc R . . C17 C 0.3543(4) 0.1868(6) 0.1293(2) 0.0493(14) Uani 1 1 d . . . H17A H 0.2886 0.1606 0.1038 0.074 Uiso 1 1 calc R . . H17B H 0.3403 0.2767 0.1436 0.074 Uiso 1 1 calc R . . H17C H 0.3646 0.1200 0.1577 0.074 Uiso 1 1 calc R . . C18 C 1.1059(4) 0.5367(6) 0.1422(2) 0.0467(14) Uani 1 1 d . . . C19 C 0.9645(4) 0.4701(5) 0.20078(19) 0.0411(13) Uani 1 1 d . . . C20 C 0.8788(5) 0.3754(6) 0.2054(2) 0.0497(15) Uani 1 1 d . . . H20 H 0.8689 0.3003 0.1822 0.060 Uiso 1 1 calc R . . C21 C 0.8092(5) 0.3891(6) 0.2427(2) 0.0559(16) Uani 1 1 d . . . H21 H 0.7511 0.3230 0.2450 0.067 Uiso 1 1 calc R . . C22 C 0.8200(5) 0.4969(6) 0.27772(19) 0.0481(14) Uani 1 1 d . . . C23 C 0.9043(5) 0.5907(6) 0.2721(2) 0.0466(14) Uani 1 1 d . . . H23 H 0.9130 0.6662 0.2952 0.056 Uiso 1 1 calc R . . C24 C 0.9762(4) 0.5807(6) 0.2349(2) 0.0456(14) Uani 1 1 d . . . H24 H 1.0331 0.6479 0.2323 0.055 Uiso 1 1 calc R . . C25 C 0.7428(6) 0.5092(7) 0.3193(2) 0.0639(17) Uani 1 1 d . . . H25A H 0.6627 0.4972 0.3036 0.096 Uiso 1 1 calc R . . H25B H 0.7524 0.5992 0.3355 0.096 Uiso 1 1 calc R . . H25C H 0.7630 0.4390 0.3459 0.096 Uiso 1 1 calc R . . C26 C 1.2687(4) 0.3134(5) -0.05615(18) 0.0328(11) Uani 1 1 d . . . C27 C 1.3842(4) 0.2854(5) -0.03944(19) 0.0356(12) Uani 1 1 d . . . H27 H 1.4086 0.2660 -0.0037 0.043 Uiso 1 1 calc R . . C28 C 1.4628(4) 0.2854(5) -0.0739(2) 0.0391(12) Uani 1 1 d . . . H28 H 1.5407 0.2634 -0.0619 0.047 Uiso 1 1 calc R . . C29 C 1.4301(5) 0.3174(5) -0.12657(19) 0.0434(13) Uani 1 1 d . . . H29 H 1.4851 0.3186 -0.1503 0.052 Uiso 1 1 calc R . . C30 C 1.3161(4) 0.3469(5) -0.14322(19) 0.0408(13) Uani 1 1 d . . . H30 H 1.2926 0.3698 -0.1787 0.049 Uiso 1 1 calc R . . C31 C 1.2369(4) 0.3438(5) -0.10937(19) 0.0393(13) Uani 1 1 d . . . H31 H 1.1586 0.3624 -0.1219 0.047 Uiso 1 1 calc R . . F1 F 1.0010(2) 0.2273(3) 0.09228(10) 0.0398(7) Uani 1 1 d . . . F2 F 0.9199(2) 0.4156(3) 0.05252(10) 0.0388(7) Uani 1 1 d . . . N1 N 0.7579(4) 0.2110(4) 0.02899(16) 0.0377(11) Uani 1 1 d . . . H1 H 0.787(5) 0.284(6) 0.035(2) 0.045 Uiso 1 1 d . . . N2 N 0.9964(3) 0.2441(4) -0.00048(15) 0.0355(10) Uani 1 1 d . . . N3 N 1.1240(3) 0.3962(4) 0.06025(15) 0.0338(10) Uani 1 1 d . . . N4 N 1.0331(3) 0.4494(5) 0.16126(15) 0.0384(10) Uani 1 1 d . . . H4 H 1.017(4) 0.363(5) 0.146(2) 0.046 Uiso 1 1 d . . . O1 O 0.7587(3) 0.0108(4) -0.01524(16) 0.0574(11) Uani 1 1 d . . . O2 O 1.1290(4) 0.6498(5) 0.16072(18) 0.0719(13) Uani 1 1 d . . . C32 C 0.3741(10) 0.4876(13) 0.2505(4) 0.115(3) Uani 1 1 d . . . C33 C 0.2819(9) 0.4044(12) 0.2643(4) 0.137(4) Uani 1 1 d . . . H33A H 0.2581 0.3395 0.2361 0.206 Uiso 1 1 calc R . . H33B H 0.2166 0.4623 0.2696 0.206 Uiso 1 1 calc R . . H33C H 0.3083 0.3546 0.2965 0.206 Uiso 1 1 calc R . . C34 C 0.3958(13) 0.603(2) 0.2855(7) 0.268(10) Uani 1 1 d . . . H34A H 0.4237 0.5699 0.3207 0.402 Uiso 1 1 calc R . . H34B H 0.3245 0.6540 0.2860 0.402 Uiso 1 1 calc R . . H34C H 0.4539 0.6617 0.2733 0.402 Uiso 1 1 calc R . . O3 O 0.4318(11) 0.4739(12) 0.2149(3) 0.240(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 B1 0.032(3) 0.027(3) 0.033(3) 0.002(2) -0.005(2) 0.005(2) C1 0.033(3) 0.040(3) 0.042(3) -0.003(2) -0.016(2) 0.004(2) C2 0.034(3) 0.045(3) 0.053(3) -0.011(3) -0.016(2) 0.000(3) C3 0.040(3) 0.043(3) 0.048(3) -0.010(3) -0.016(3) 0.002(3) C4 0.030(3) 0.033(3) 0.041(3) -0.004(2) -0.012(2) 0.004(2) C5 0.029(3) 0.029(3) 0.037(3) 0.003(2) -0.016(2) 0.002(2) C6 0.023(2) 0.039(3) 0.038(3) 0.006(2) -0.011(2) 0.001(2) C7 0.031(3) 0.041(3) 0.037(3) 0.000(2) -0.012(2) -0.003(2) C8 0.030(3) 0.053(3) 0.044(3) -0.005(3) -0.011(2) -0.011(2) C9 0.032(3) 0.043(3) 0.038(3) -0.001(2) -0.009(2) 0.004(2) C10 0.035(3) 0.040(3) 0.044(3) -0.002(3) -0.021(2) 0.005(2) C11 0.030(3) 0.033(3) 0.031(3) 0.001(2) -0.013(2) -0.002(2) C12 0.037(3) 0.038(3) 0.042(3) 0.003(2) -0.016(2) -0.002(2) C13 0.036(3) 0.038(3) 0.044(3) 0.007(2) -0.019(2) -0.006(2) C14 0.031(3) 0.044(3) 0.032(3) 0.006(2) -0.016(2) -0.005(2) C15 0.040(3) 0.042(3) 0.029(3) -0.001(2) -0.012(2) 0.000(2) C16 0.032(3) 0.038(3) 0.032(3) 0.000(2) -0.009(2) -0.005(2) C17 0.042(3) 0.054(3) 0.047(3) 0.004(3) -0.014(3) -0.002(3) C18 0.035(3) 0.055(4) 0.046(3) -0.003(3) -0.014(2) -0.005(3) C19 0.036(3) 0.049(3) 0.032(3) -0.002(2) -0.017(2) 0.001(2) C20 0.060(4) 0.052(4) 0.035(3) -0.003(3) -0.001(3) -0.007(3) C21 0.065(4) 0.058(4) 0.043(3) 0.006(3) 0.000(3) -0.006(3) C22 0.049(3) 0.064(4) 0.029(3) 0.004(3) -0.003(2) 0.012(3) C23 0.040(3) 0.060(4) 0.035(3) -0.007(3) -0.012(3) 0.007(3) C24 0.033(3) 0.060(4) 0.039(3) -0.007(3) -0.012(2) -0.001(3) C25 0.073(4) 0.070(4) 0.049(4) 0.011(3) 0.008(3) 0.017(4) C26 0.031(3) 0.031(3) 0.032(3) 0.000(2) -0.009(2) -0.002(2) C27 0.033(3) 0.034(3) 0.035(3) -0.001(2) -0.011(2) -0.001(2) C28 0.029(3) 0.039(3) 0.046(3) -0.005(2) -0.005(2) 0.000(2) C29 0.045(3) 0.049(3) 0.035(3) -0.007(2) -0.003(2) -0.006(3) C30 0.041(3) 0.049(3) 0.029(3) -0.007(2) -0.006(2) -0.005(2) C31 0.032(3) 0.041(3) 0.039(3) -0.002(2) -0.013(2) -0.001(2) F1 0.0409(16) 0.0382(16) 0.0367(15) 0.0020(13) -0.0081(12) -0.0039(13) F2 0.0294(15) 0.0365(15) 0.0460(16) -0.0026(13) -0.0111(12) 0.0013(12) N1 0.035(3) 0.036(2) 0.039(2) -0.004(2) -0.0077(19) -0.003(2) N2 0.031(2) 0.034(2) 0.036(2) -0.0036(18) -0.0150(18) -0.0008(18) N3 0.030(2) 0.034(2) 0.032(2) 0.0008(18) -0.0164(18) -0.0035(18) N4 0.034(2) 0.047(3) 0.032(2) -0.004(2) -0.0041(19) -0.002(2) O1 0.041(2) 0.048(2) 0.075(3) -0.023(2) -0.0173(19) -0.0060(19) O2 0.072(3) 0.067(3) 0.080(3) -0.036(3) 0.020(2) -0.028(2) C32 0.131(9) 0.151(10) 0.061(5) -0.017(6) 0.006(6) 0.026(8) C33 0.100(8) 0.156(10) 0.154(10) 0.082(8) 0.011(7) 0.048(7) C34 0.144(12) 0.38(3) 0.28(2) -0.15(2) 0.012(13) -0.102(15) O3 0.363(15) 0.261(12) 0.122(7) -0.062(8) 0.130(9) -0.084(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 B1 F1 1.403(6) . ? B1 F2 1.404(6) . ? B1 N2 1.532(7) . ? B1 N3 1.539(7) . ? C1 N2 1.363(6) . ? C1 C2 1.402(7) . ? C1 C10 1.479(8) . ? C2 C3 1.358(7) . ? C2 H2 0.9500 . ? C3 C4 1.402(7) . ? C3 H3 0.9500 . ? C4 N2 1.382(6) . ? C4 C5 1.398(6) . ? C5 C6 1.401(7) . ? C5 C26 1.451(7) . ? C6 N3 1.381(6) . ? C6 C7 1.402(6) . ? C7 C8 1.364(7) . ? C7 H7 0.9500 . ? C8 C9 1.394(7) . ? C8 H8 0.9500 . ? C9 N3 1.362(6) . ? C9 C18 1.487(8) . ? C10 O1 1.221(6) . ? C10 N1 1.360(7) . ? C11 N1 1.395(7) . ? C11 C16 1.400(7) . ? C11 C12 1.401(7) . ? C12 C13 1.367(7) . ? C12 H12 0.9500 . ? C13 C14 1.382(7) . ? C13 H13 0.9500 . ? C14 C15 1.395(7) . ? C14 C17 1.496(7) . ? C15 C16 1.357(7) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 O2 1.226(6) . ? C18 N4 1.351(7) . ? C19 C20 1.389(7) . ? C19 C24 1.395(7) . ? C19 N4 1.400(7) . ? C20 C21 1.354(8) . ? C20 H20 0.9500 . ? C21 C22 1.389(8) . ? C21 H21 0.9500 . ? C22 C23 1.375(8) . ? C22 C25 1.504(8) . ? C23 C24 1.368(7) . ? C23 H23 0.9500 . ? C24 H24 0.9500 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 C27 1.394(6) . ? C26 C31 1.409(6) . ? C27 C28 1.368(7) . ? C27 H27 0.9500 . ? C28 C29 1.401(7) . ? C28 H28 0.9500 . ? C29 C30 1.381(7) . ? C29 H29 0.9500 . ? C30 C31 1.362(7) . ? C30 H30 0.9500 . ? C31 H31 0.9500 . ? N1 H1 0.80(5) . ? N4 H4 0.95(5) . ? C32 O3 1.222(12) . ? C32 C33 1.441(14) . ? C32 C34 1.449(16) . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? 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 B1 F2 107.5(4) . . ? F1 B1 N2 109.5(4) . . ? F2 B1 N2 111.1(4) . . ? F1 B1 N3 110.7(4) . . ? F2 B1 N3 108.3(4) . . ? N2 B1 N3 109.7(4) . . ? N2 C1 C2 109.0(5) . . ? N2 C1 C10 129.6(5) . . ? C2 C1 C10 121.3(4) . . ? C3 C2 C1 107.6(5) . . ? C3 C2 H2 126.2 . . ? C1 C2 H2 126.2 . . ? C2 C3 C4 107.9(5) . . ? C2 C3 H3 126.1 . . ? C4 C3 H3 126.1 . . ? N2 C4 C5 121.8(4) . . ? N2 C4 C3 108.2(4) . . ? C5 C4 C3 129.9(5) . . ? C4 C5 C6 120.2(5) . . ? C4 C5 C26 120.1(4) . . ? C6 C5 C26 119.7(4) . . ? N3 C6 C5 121.5(4) . . ? N3 C6 C7 108.4(4) . . ? C5 C6 C7 129.8(5) . . ? C8 C7 C6 107.7(5) . . ? C8 C7 H7 126.2 . . ? C6 C7 H7 126.2 . . ? C7 C8 C9 107.4(4) . . ? C7 C8 H8 126.3 . . ? C9 C8 H8 126.3 . . ? N3 C9 C8 109.5(5) . . ? N3 C9 C18 128.3(5) . . ? C8 C9 C18 122.2(5) . . ? O1 C10 N1 123.9(5) . . ? O1 C10 C1 118.5(5) . . ? N1 C10 C1 117.6(5) . . ? N1 C11 C16 118.0(4) . . ? N1 C11 C12 124.6(5) . . ? C16 C11 C12 117.4(5) . . ? C13 C12 C11 120.4(5) . . ? C13 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? C12 C13 C14 122.7(5) . . ? C12 C13 H13 118.6 . . ? C14 C13 H13 118.6 . . ? C13 C14 C15 116.2(5) . . ? C13 C14 C17 121.3(5) . . ? C15 C14 C17 122.5(5) . . ? C16 C15 C14 122.6(5) . . ? C16 C15 H15 118.7 . . ? C14 C15 H15 118.7 . . ? C15 C16 C11 120.7(5) . . ? C15 C16 H16 119.7 . . ? C11 C16 H16 119.7 . . ? C14 C17 H17A 109.5 . . ? C14 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C14 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? O2 C18 N4 123.5(6) . . ? O2 C18 C9 118.7(5) . . ? N4 C18 C9 117.8(5) . . ? C20 C19 C24 118.5(5) . . ? C20 C19 N4 117.5(5) . . ? C24 C19 N4 124.0(5) . . ? C21 C20 C19 120.7(5) . . ? C21 C20 H20 119.6 . . ? C19 C20 H20 119.6 . . ? C20 C21 C22 122.0(6) . . ? C20 C21 H21 119.0 . . ? C22 C21 H21 119.0 . . ? C23 C22 C21 116.5(5) . . ? C23 C22 C25 122.3(5) . . ? C21 C22 C25 121.1(6) . . ? C24 C23 C22 123.2(5) . . ? C24 C23 H23 118.4 . . ? C22 C23 H23 118.4 . . ? C23 C24 C19 119.0(5) . . ? C23 C24 H24 120.5 . . ? C19 C24 H24 120.5 . . ? C22 C25 H25A 109.5 . . ? C22 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C22 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C27 C26 C31 117.6(5) . . ? C27 C26 C5 121.5(4) . . ? C31 C26 C5 120.9(4) . . ? C28 C27 C26 120.9(4) . . ? C28 C27 H27 119.6 . . ? C26 C27 H27 119.6 . . ? C27 C28 C29 120.9(5) . . ? C27 C28 H28 119.5 . . ? C29 C28 H28 119.5 . . ? C30 C29 C28 118.5(5) . . ? C30 C29 H29 120.8 . . ? C28 C29 H29 120.8 . . ? C31 C30 C29 120.9(5) . . ? C31 C30 H30 119.6 . . ? C29 C30 H30 119.6 . . ? C30 C31 C26 121.3(5) . . ? C30 C31 H31 119.4 . . ? C26 C31 H31 119.4 . . ? C10 N1 C11 128.7(5) . . ? C10 N1 H1 121(4) . . ? C11 N1 H1 111(4) . . ? C1 N2 C4 107.4(4) . . ? C1 N2 B1 128.7(5) . . ? C4 N2 B1 123.2(4) . . ? C9 N3 C6 107.1(4) . . ? C9 N3 B1 129.0(4) . . ? C6 N3 B1 123.3(4) . . ? C18 N4 C19 129.0(5) . . ? C18 N4 H4 121(3) . . ? C19 N4 H4 109(3) . . ? O3 C32 C33 129.5(12) . . ? O3 C32 C34 119.2(14) . . ? C33 C32 C34 111.3(11) . . ? C32 C33 H33A 109.5 . . ? C32 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C32 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C32 C34 H34A 109.5 . . ? C32 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C32 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N2 C1 C2 C3 -0.4(6) . . . . ? C10 C1 C2 C3 -178.5(4) . . . . ? C1 C2 C3 C4 0.5(6) . . . . ? C2 C3 C4 N2 -0.4(6) . . . . ? C2 C3 C4 C5 176.0(5) . . . . ? N2 C4 C5 C6 2.4(7) . . . . ? C3 C4 C5 C6 -173.5(5) . . . . ? N2 C4 C5 C26 -175.2(4) . . . . ? C3 C4 C5 C26 8.9(8) . . . . ? C4 C5 C6 N3 1.0(7) . . . . ? C26 C5 C6 N3 178.6(4) . . . . ? C4 C5 C6 C7 -171.5(5) . . . . ? C26 C5 C6 C7 6.1(7) . . . . ? N3 C6 C7 C8 -0.8(5) . . . . ? C5 C6 C7 C8 172.4(5) . . . . ? C6 C7 C8 C9 0.6(6) . . . . ? C7 C8 C9 N3 -0.3(6) . . . . ? C7 C8 C9 C18 -179.7(4) . . . . ? N2 C1 C10 O1 -157.7(5) . . . . ? C2 C1 C10 O1 20.0(7) . . . . ? N2 C1 C10 N1 24.5(7) . . . . ? C2 C1 C10 N1 -157.8(5) . . . . ? N1 C11 C12 C13 179.6(4) . . . . ? C16 C11 C12 C13 1.1(6) . . . . ? C11 C12 C13 C14 -0.1(7) . . . . ? C12 C13 C14 C15 -0.6(7) . . . . ? C12 C13 C14 C17 179.2(4) . . . . ? C13 C14 C15 C16 0.4(7) . . . . ? C17 C14 C15 C16 -179.5(4) . . . . ? C14 C15 C16 C11 0.6(7) . . . . ? N1 C11 C16 C15 -179.9(4) . . . . ? C12 C11 C16 C15 -1.4(6) . . . . ? N3 C9 C18 O2 -156.5(5) . . . . ? C8 C9 C18 O2 22.8(7) . . . . ? N3 C9 C18 N4 24.1(7) . . . . ? C8 C9 C18 N4 -156.6(5) . . . . ? C24 C19 C20 C21 -1.0(8) . . . . ? N4 C19 C20 C21 -179.9(5) . . . . ? C19 C20 C21 C22 -0.1(8) . . . . ? C20 C21 C22 C23 1.0(8) . . . . ? C20 C21 C22 C25 -179.2(5) . . . . ? C21 C22 C23 C24 -0.9(8) . . . . ? C25 C22 C23 C24 179.3(5) . . . . ? C22 C23 C24 C19 -0.2(8) . . . . ? C20 C19 C24 C23 1.1(7) . . . . ? N4 C19 C24 C23 180.0(4) . . . . ? C4 C5 C26 C27 -129.6(5) . . . . ? C6 C5 C26 C27 52.8(6) . . . . ? C4 C5 C26 C31 51.1(7) . . . . ? C6 C5 C26 C31 -126.5(5) . . . . ? C31 C26 C27 C28 -1.0(7) . . . . ? C5 C26 C27 C28 179.7(5) . . . . ? C26 C27 C28 C29 1.8(7) . . . . ? C27 C28 C29 C30 -1.0(8) . . . . ? C28 C29 C30 C31 -0.7(8) . . . . ? C29 C30 C31 C26 1.5(8) . . . . ? C27 C26 C31 C30 -0.6(7) . . . . ? C5 C26 C31 C30 178.7(5) . . . . ? O1 C10 N1 C11 4.0(8) . . . . ? C1 C10 N1 C11 -178.3(4) . . . . ? C16 C11 N1 C10 -176.4(4) . . . . ? C12 C11 N1 C10 5.1(7) . . . . ? C2 C1 N2 C4 0.2(5) . . . . ? C10 C1 N2 C4 178.1(5) . . . . ? C2 C1 N2 B1 -170.4(4) . . . . ? C10 C1 N2 B1 7.6(8) . . . . ? C5 C4 N2 C1 -176.6(4) . . . . ? C3 C4 N2 C1 0.1(5) . . . . ? C5 C4 N2 B1 -5.4(7) . . . . ? C3 C4 N2 B1 171.3(4) . . . . ? F1 B1 N2 C1 52.1(6) . . . . ? F2 B1 N2 C1 -66.6(6) . . . . ? N3 B1 N2 C1 173.8(4) . . . . ? F1 B1 N2 C4 -117.1(5) . . . . ? F2 B1 N2 C4 124.3(5) . . . . ? N3 B1 N2 C4 4.6(6) . . . . ? C8 C9 N3 C6 -0.2(5) . . . . ? C18 C9 N3 C6 179.2(5) . . . . ? C8 C9 N3 B1 -171.6(4) . . . . ? C18 C9 N3 B1 7.8(8) . . . . ? C5 C6 N3 C9 -173.3(4) . . . . ? C7 C6 N3 C9 0.6(5) . . . . ? C5 C6 N3 B1 -1.3(7) . . . . ? C7 C6 N3 B1 172.6(4) . . . . ? F1 B1 N3 C9 -70.2(6) . . . . ? F2 B1 N3 C9 47.4(6) . . . . ? N2 B1 N3 C9 168.8(4) . . . . ? F1 B1 N3 C6 119.7(5) . . . . ? F2 B1 N3 C6 -122.7(4) . . . . ? N2 B1 N3 C6 -1.3(6) . . . . ? O2 C18 N4 C19 5.6(8) . . . . ? C9 C18 N4 C19 -175.0(4) . . . . ? C20 C19 N4 C18 166.2(5) . . . . ? C24 C19 N4 C18 -12.7(8) . . . . ? 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 H1 F2 0.80(5) 2.03(5) 2.780(5) 156(5) . N4 H4 F1 0.95(5) 1.92(5) 2.813(5) 157(5) . _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.629 _refine_diff_density_min -0.430 _refine_diff_density_rms 0.072