# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _publ_section_title ;Free base tripyrrins ; _publ_contact_author_name 'Prof. Martin Broring' _publ_contact_author_email MARTIN.BROERING@CHEMIE.UNI-MARBURG.DE loop_ _publ_author_name 'Martin Broring' 'Serguei Prikhodovski' 'Esther Consul Tejero' # Attachment 'structure.cif' data_sp19ec _database_code_depnum_ccdc_archive 'CCDC 626329' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H51 N3' _chemical_formula_weight 501.78 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.1869(9) _cell_length_b 24.340(2) _cell_length_c 11.6741(11) _cell_angle_alpha 90.00 _cell_angle_beta 93.714(10) _cell_angle_gamma 90.00 _cell_volume 3172.1(5) _cell_formula_units_Z 4 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 6954 _cell_measurement_theta_min 2.00 _cell_measurement_theta_max 25.65 _exptl_crystal_description cube _exptl_crystal_colour green _exptl_crystal_size_max 0.11 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.051 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1104 _exptl_absorpt_coefficient_mu 0.061 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 193(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 'IPDS1 (Stoe)' _diffrn_measurement_method phi-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24891 _diffrn_reflns_av_R_equivalents 0.1174 _diffrn_reflns_av_sigmaI/netI 0.1642 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 26.04 _reflns_number_total 6006 _reflns_number_gt 2378 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'STOE WinXpose (X-Area)' _computing_cell_refinement 'STOE Wincell (X-Area)' _computing_data_reduction 'STOE WinIntegrate (X-Area)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Mercury 1.4' _computing_publication_material 'WinGx-Version 1.70.00' _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^)+(0.0118P)^2^+0.0000P] 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 0.0039(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 6006 _refine_ls_number_parameters 351 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1263 _refine_ls_R_factor_gt 0.0377 _refine_ls_wR_factor_ref 0.0682 _refine_ls_wR_factor_gt 0.0554 _refine_ls_goodness_of_fit_ref 0.690 _refine_ls_restrained_S_all 0.690 _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 0.3009(2) 0.57342(8) 0.36415(16) 0.0428(5) Uani 1 1 d . . . C2 C 0.28563(19) 0.62337(7) 0.43804(16) 0.0360(5) Uani 1 1 d . . . C3 C 0.34167(19) 0.63386(8) 0.55524(16) 0.0386(5) Uani 1 1 d . . . C4 C 0.30168(18) 0.68379(8) 0.58613(16) 0.0349(5) Uani 1 1 d . . . C5 C 0.22198(18) 0.70349(8) 0.49145(16) 0.0340(5) Uani 1 1 d . . . C6 C 0.16488(18) 0.75213(8) 0.48339(16) 0.0352(5) Uani 1 1 d . . . H6 H 0.1766 0.7754 0.5485 0.042 Uiso 1 1 calc R . . C7 C 0.08924(18) 0.77377(7) 0.39098(15) 0.0330(5) Uani 1 1 d . . . C8 C 0.05923(18) 0.82867(7) 0.37039(15) 0.0328(5) Uani 1 1 d . . . C9 C -0.00830(18) 0.83109(7) 0.26490(16) 0.0343(5) Uani 1 1 d . . . C10 C -0.02202(18) 0.77704(7) 0.22470(15) 0.0345(5) Uani 1 1 d . . . C11 C -0.09383(18) 0.75776(8) 0.12683(15) 0.0369(5) Uani 1 1 d . . . H11 H -0.1158 0.7843 0.0696 0.044 Uiso 1 1 calc R . . C12 C -0.13365(19) 0.70622(8) 0.10698(17) 0.0372(5) Uani 1 1 d . . . C13 C -0.20888(19) 0.68608(8) 0.00864(16) 0.0391(5) Uani 1 1 d . . . C14 C -0.22907(19) 0.63217(9) 0.02848(16) 0.0429(6) Uani 1 1 d . . . C15 C -0.16562(19) 0.61960(8) 0.14149(16) 0.0390(5) Uani 1 1 d . . . C16 C -0.1593(2) 0.56569(8) 0.20452(17) 0.0442(5) Uani 1 1 d . . . C17 C 0.2451(2) 0.58415(8) 0.24248(17) 0.0565(6) Uani 1 1 d . . . H17A H 0.1606 0.5942 0.2465 0.085 Uiso 1 1 calc R . . H17B H 0.2510 0.5509 0.1960 0.085 Uiso 1 1 calc R . . H17C H 0.2879 0.6142 0.2073 0.085 Uiso 1 1 calc R . . C18 C 0.2374(2) 0.52441(8) 0.41535(19) 0.0574(7) Uani 1 1 d . . . H18A H 0.2729 0.5170 0.4928 0.086 Uiso 1 1 calc R . . H18B H 0.2467 0.4920 0.3669 0.086 Uiso 1 1 calc R . . H18C H 0.1521 0.5328 0.4191 0.086 Uiso 1 1 calc R . . C19 C 0.4337(2) 0.56064(9) 0.35323(19) 0.0598(7) Uani 1 1 d . . . H19A H 0.4739 0.5932 0.3246 0.090 Uiso 1 1 calc R . . H19B H 0.4414 0.5301 0.2995 0.090 Uiso 1 1 calc R . . H19C H 0.4708 0.5505 0.4286 0.090 Uiso 1 1 calc R . . C20 C 0.42654(19) 0.59756(8) 0.62643(17) 0.0471(6) Uani 1 1 d . . . H20A H 0.4189 0.5595 0.5972 0.057 Uiso 1 1 calc R . . H20B H 0.4025 0.5975 0.7066 0.057 Uiso 1 1 calc R . . C21 C 0.5574(2) 0.61502(9) 0.6261(2) 0.0612(7) Uani 1 1 d . . . H21A H 0.5830 0.6138 0.5475 0.092 Uiso 1 1 calc R . . H21B H 0.6070 0.5899 0.6746 0.092 Uiso 1 1 calc R . . H21C H 0.5662 0.6525 0.6561 0.092 Uiso 1 1 calc R . . C22 C 0.3297(2) 0.71528(8) 0.69482(16) 0.0474(6) Uani 1 1 d . . . H22A H 0.3655 0.6898 0.7536 0.057 Uiso 1 1 calc R . . H22B H 0.2539 0.7293 0.7229 0.057 Uiso 1 1 calc R . . C23 C 0.4149(2) 0.76355(9) 0.68250(18) 0.0609(7) Uani 1 1 d . . . H23A H 0.4934 0.7498 0.6632 0.091 Uiso 1 1 calc R . . H23B H 0.4233 0.7839 0.7550 0.091 Uiso 1 1 calc R . . H23C H 0.3826 0.7880 0.6213 0.091 Uiso 1 1 calc R . . C24 C 0.09875(19) 0.87560(7) 0.44669(16) 0.0400(5) Uani 1 1 d . . . H24A H 0.0930 0.8645 0.5277 0.048 Uiso 1 1 calc R . . H24B H 0.0439 0.9070 0.4313 0.048 Uiso 1 1 calc R . . C25 C 0.2261(2) 0.89392(8) 0.42958(18) 0.0492(6) Uani 1 1 d . . . H25A H 0.2818 0.8642 0.4522 0.074 Uiso 1 1 calc R . . H25B H 0.2451 0.9264 0.4769 0.074 Uiso 1 1 calc R . . H25C H 0.2337 0.9030 0.3486 0.074 Uiso 1 1 calc R . . C26 C -0.0584(2) 0.88132(7) 0.20491(18) 0.0421(5) Uani 1 1 d . . . H26A H -0.0738 0.9097 0.2629 0.051 Uiso 1 1 calc R . . H26B H -0.1360 0.8719 0.1639 0.051 Uiso 1 1 calc R . . C27 C 0.0247(2) 0.90483(8) 0.11976(17) 0.0506(6) Uani 1 1 d . . . H27A H 0.1011 0.9150 0.1601 0.076 Uiso 1 1 calc R . . H27B H -0.0122 0.9374 0.0831 0.076 Uiso 1 1 calc R . . H27C H 0.0389 0.8772 0.0611 0.076 Uiso 1 1 calc R . . C28 C -0.2521(2) 0.72098(9) -0.09098(17) 0.0512(6) Uani 1 1 d . . . H28A H -0.2792 0.6967 -0.1556 0.061 Uiso 1 1 calc R . . H28B H -0.1841 0.7430 -0.1159 0.061 Uiso 1 1 calc R . . C29 C -0.3543(3) 0.75973(11) -0.0655(2) 0.0772(9) Uani 1 1 d . . . H29A H -0.4252 0.7382 -0.0492 0.116 Uiso 1 1 calc R . . H29B H -0.3731 0.7834 -0.1322 0.116 Uiso 1 1 calc R . . H29C H -0.3302 0.7825 0.0013 0.116 Uiso 1 1 calc R . . C30 C -0.3005(2) 0.59381(9) -0.05045(18) 0.0578(7) Uani 1 1 d . . . H30A H -0.2759 0.5556 -0.0322 0.069 Uiso 1 1 calc R . . H30B H -0.2812 0.6014 -0.1305 0.069 Uiso 1 1 calc R . . C31 C -0.4358(2) 0.59870(11) -0.0423(2) 0.0836(9) Uani 1 1 d . . . H31A H -0.4558 0.5921 0.0370 0.125 Uiso 1 1 calc R . . H31B H -0.4765 0.5715 -0.0929 0.125 Uiso 1 1 calc R . . H31C H -0.4620 0.6357 -0.0658 0.125 Uiso 1 1 calc R . . C32 C -0.2840(2) 0.53977(9) 0.2113(2) 0.0657(7) Uani 1 1 d . . . H32A H -0.3388 0.5669 0.2412 0.099 Uiso 1 1 calc R . . H32B H -0.2783 0.5079 0.2626 0.099 Uiso 1 1 calc R . . H32C H -0.3143 0.5281 0.1345 0.099 Uiso 1 1 calc R . . C33 C -0.1069(2) 0.57448(8) 0.32786(17) 0.0545(6) Uani 1 1 d . . . H33A H -0.0265 0.5904 0.3263 0.082 Uiso 1 1 calc R . . H33B H -0.1020 0.5391 0.3681 0.082 Uiso 1 1 calc R . . H33C H -0.1586 0.5995 0.3680 0.082 Uiso 1 1 calc R . . C34 C -0.0777(2) 0.52642(8) 0.14333(18) 0.0527(6) Uani 1 1 d . . . H34A H -0.1102 0.5206 0.0643 0.079 Uiso 1 1 calc R . . H34B H -0.0734 0.4912 0.1839 0.079 Uiso 1 1 calc R . . H34C H 0.0028 0.5423 0.1426 0.079 Uiso 1 1 calc R . . N1 N 0.21531(15) 0.66378(6) 0.40248(13) 0.0374(4) Uani 1 1 d . . . N2 N 0.03863(17) 0.74314(6) 0.30178(14) 0.0351(4) Uani 1 1 d . . . N3 N -0.10926(15) 0.66273(6) 0.18490(13) 0.0379(4) Uani 1 1 d . . . H H 0.043(2) 0.7054(8) 0.3004(19) 0.061(6) 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 0.0405(16) 0.0368(11) 0.0516(13) -0.0002(9) 0.0067(11) 0.0055(10) C2 0.0327(14) 0.0336(11) 0.0423(12) 0.0052(9) 0.0071(10) 0.0032(10) C3 0.0320(15) 0.0422(12) 0.0415(12) 0.0093(10) 0.0024(10) 0.0028(10) C4 0.0305(14) 0.0406(12) 0.0334(11) 0.0046(9) 0.0015(10) -0.0002(9) C5 0.0328(14) 0.0346(11) 0.0345(12) 0.0043(9) 0.0022(10) 0.0021(10) C6 0.0345(14) 0.0376(11) 0.0334(11) 0.0009(9) 0.0020(9) -0.0010(10) C7 0.0334(14) 0.0342(11) 0.0313(11) 0.0012(9) 0.0019(10) 0.0006(9) C8 0.0340(14) 0.0301(11) 0.0344(11) -0.0017(8) 0.0035(9) 0.0041(9) C9 0.0346(14) 0.0307(11) 0.0381(12) 0.0048(9) 0.0047(10) 0.0075(9) C10 0.0357(15) 0.0337(11) 0.0337(12) 0.0028(9) -0.0009(10) 0.0049(9) C11 0.0332(14) 0.0413(12) 0.0361(12) 0.0028(9) 0.0011(10) 0.0078(10) C12 0.0359(15) 0.0394(12) 0.0361(12) -0.0018(10) 0.0016(10) 0.0027(10) C13 0.0336(15) 0.0520(13) 0.0314(11) -0.0056(10) -0.0010(10) 0.0044(10) C14 0.0317(15) 0.0561(15) 0.0411(13) -0.0125(11) 0.0031(10) -0.0028(11) C15 0.0311(14) 0.0428(12) 0.0435(12) -0.0064(10) 0.0041(10) -0.0011(10) C16 0.0423(16) 0.0404(12) 0.0506(13) -0.0034(10) 0.0089(11) -0.0054(10) C17 0.0642(18) 0.0552(14) 0.0497(14) -0.0092(11) -0.0006(12) 0.0023(12) C18 0.0594(18) 0.0396(13) 0.0735(16) 0.0006(11) 0.0071(13) -0.0013(11) C19 0.0514(19) 0.0571(15) 0.0716(16) -0.0077(12) 0.0105(13) 0.0129(12) C20 0.0446(17) 0.0499(13) 0.0463(13) 0.0110(10) -0.0009(11) 0.0103(11) C21 0.0460(19) 0.0629(15) 0.0728(17) 0.0108(12) -0.0114(13) 0.0121(12) C22 0.0468(16) 0.0580(14) 0.0370(12) 0.0039(10) -0.0013(11) 0.0092(11) C23 0.061(2) 0.0618(15) 0.0572(16) -0.0143(12) -0.0148(13) 0.0022(12) C24 0.0447(16) 0.0345(11) 0.0408(12) 0.0003(9) 0.0019(10) 0.0022(10) C25 0.0509(17) 0.0446(13) 0.0516(13) -0.0019(10) -0.0001(11) -0.0070(11) C26 0.0451(16) 0.0375(10) 0.0432(11) 0.0012(10) -0.0011(10) 0.0068(11) C27 0.0661(18) 0.0426(12) 0.0432(13) 0.0090(9) 0.0044(11) 0.0103(11) C28 0.0483(17) 0.0682(15) 0.0360(12) -0.0040(11) -0.0048(11) 0.0047(13) C29 0.068(2) 0.097(2) 0.0636(17) 0.0043(14) -0.0145(14) 0.0336(16) C30 0.0506(19) 0.0702(16) 0.0515(15) -0.0129(12) -0.0041(12) -0.0107(13) C31 0.049(2) 0.114(2) 0.086(2) -0.0107(16) -0.0151(15) -0.0200(17) C32 0.055(2) 0.0705(16) 0.0731(17) 0.0013(13) 0.0142(13) -0.0172(14) C33 0.0655(19) 0.0489(13) 0.0494(13) 0.0051(10) 0.0060(12) -0.0009(12) C34 0.0565(18) 0.0427(13) 0.0591(14) -0.0037(10) 0.0056(12) -0.0011(11) N1 0.0379(12) 0.0354(9) 0.0388(10) 0.0002(8) 0.0021(8) 0.0031(8) N2 0.0392(12) 0.0292(9) 0.0367(9) 0.0017(9) 0.0000(8) 0.0032(9) N3 0.0389(12) 0.0353(9) 0.0393(10) -0.0016(8) -0.0005(8) 0.0030(8) _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 C2 1.507(3) . ? C1 C18 1.530(3) . ? C1 C19 1.531(3) . ? C1 C17 1.537(3) . ? C2 N1 1.310(2) . ? C2 C3 1.490(3) . ? C3 C4 1.352(2) . ? C3 C20 1.507(3) . ? C4 C5 1.456(3) . ? C4 C22 1.498(3) . ? C5 C6 1.346(2) . ? C5 N1 1.417(2) . ? C6 C7 1.428(3) . ? C7 N2 1.373(2) . ? C7 C8 1.395(2) . ? C8 C9 1.404(2) . ? C8 C24 1.498(2) . ? C9 C10 1.402(2) . ? C9 C26 1.499(2) . ? C10 N2 1.368(2) . ? C10 C11 1.432(3) . ? C11 C12 1.346(3) . ? C12 N3 1.411(2) . ? C12 C13 1.463(3) . ? C13 C14 1.354(3) . ? C13 C28 1.495(3) . ? C14 C15 1.489(3) . ? C14 C30 1.505(3) . ? C15 N3 1.310(2) . ? C15 C16 1.504(3) . ? C16 C34 1.530(3) . ? C16 C33 1.534(3) . ? C16 C32 1.538(3) . ? C20 C21 1.524(3) . ? C22 C23 1.525(3) . ? C24 C25 1.519(3) . ? C26 C27 1.517(3) . ? C28 C29 1.526(3) . ? C30 C31 1.527(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 C2 C1 C18 109.44(17) . . ? C2 C1 C19 111.00(18) . . ? C18 C1 C19 110.59(17) . . ? C2 C1 C17 109.73(16) . . ? C18 C1 C17 108.81(18) . . ? C19 C1 C17 107.23(18) . . ? N1 C2 C3 111.77(16) . . ? N1 C2 C1 120.83(17) . . ? C3 C2 C1 127.39(17) . . ? C4 C3 C2 105.79(16) . . ? C4 C3 C20 125.98(18) . . ? C2 C3 C20 128.23(17) . . ? C3 C4 C5 106.89(17) . . ? C3 C4 C22 129.13(18) . . ? C5 C4 C22 123.98(17) . . ? C6 C5 N1 123.14(17) . . ? C6 C5 C4 127.40(18) . . ? N1 C5 C4 109.42(16) . . ? C5 C6 C7 129.24(18) . . ? N2 C7 C8 107.86(16) . . ? N2 C7 C6 124.61(16) . . ? C8 C7 C6 127.43(17) . . ? C7 C8 C9 107.53(16) . . ? C7 C8 C24 124.73(17) . . ? C9 C8 C24 127.68(16) . . ? C10 C9 C8 107.18(16) . . ? C10 C9 C26 125.40(17) . . ? C8 C9 C26 127.42(17) . . ? N2 C10 C9 107.87(16) . . ? N2 C10 C11 123.76(17) . . ? C9 C10 C11 128.16(17) . . ? C12 C11 C10 127.21(18) . . ? C11 C12 N3 122.70(18) . . ? C11 C12 C13 127.89(18) . . ? N3 C12 C13 109.39(16) . . ? C14 C13 C12 106.51(17) . . ? C14 C13 C28 129.38(18) . . ? C12 C13 C28 124.11(18) . . ? C13 C14 C15 105.99(16) . . ? C13 C14 C30 125.77(19) . . ? C15 C14 C30 128.23(19) . . ? N3 C15 C14 111.59(17) . . ? N3 C15 C16 120.27(18) . . ? C14 C15 C16 128.13(18) . . ? C15 C16 C34 109.09(17) . . ? C15 C16 C33 109.90(16) . . ? C34 C16 C33 108.77(18) . . ? C15 C16 C32 111.67(18) . . ? C34 C16 C32 109.79(17) . . ? C33 C16 C32 107.57(18) . . ? C3 C20 C21 113.95(17) . . ? C4 C22 C23 114.33(17) . . ? C8 C24 C25 112.89(17) . . ? C9 C26 C27 112.78(18) . . ? C13 C28 C29 114.08(19) . . ? C14 C30 C31 113.74(19) . . ? C2 N1 C5 106.13(15) . . ? C10 N2 C7 109.52(14) . . ? C15 N3 C12 106.49(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 C18 C1 C2 N1 -108.3(2) . . . . ? C19 C1 C2 N1 129.4(2) . . . . ? C17 C1 C2 N1 11.0(3) . . . . ? C18 C1 C2 C3 70.6(3) . . . . ? C19 C1 C2 C3 -51.7(3) . . . . ? C17 C1 C2 C3 -170.09(19) . . . . ? N1 C2 C3 C4 -1.2(2) . . . . ? C1 C2 C3 C4 179.87(19) . . . . ? N1 C2 C3 C20 179.4(2) . . . . ? C1 C2 C3 C20 0.4(3) . . . . ? C2 C3 C4 C5 0.6(2) . . . . ? C20 C3 C4 C5 -179.9(2) . . . . ? C2 C3 C4 C22 -179.4(2) . . . . ? C20 C3 C4 C22 0.1(4) . . . . ? C3 C4 C5 C6 -177.7(2) . . . . ? C22 C4 C5 C6 2.3(3) . . . . ? C3 C4 C5 N1 0.0(2) . . . . ? C22 C4 C5 N1 -179.98(17) . . . . ? N1 C5 C6 C7 0.3(3) . . . . ? C4 C5 C6 C7 177.8(2) . . . . ? C5 C6 C7 N2 15.7(4) . . . . ? C5 C6 C7 C8 -160.1(2) . . . . ? N2 C7 C8 C9 -1.5(2) . . . . ? C6 C7 C8 C9 174.8(2) . . . . ? N2 C7 C8 C24 -178.95(18) . . . . ? C6 C7 C8 C24 -2.6(3) . . . . ? C7 C8 C9 C10 2.1(2) . . . . ? C24 C8 C9 C10 179.38(19) . . . . ? C7 C8 C9 C26 -178.4(2) . . . . ? C24 C8 C9 C26 -1.1(4) . . . . ? C8 C9 C10 N2 -1.8(2) . . . . ? C26 C9 C10 N2 178.6(2) . . . . ? C8 C9 C10 C11 173.1(2) . . . . ? C26 C9 C10 C11 -6.4(3) . . . . ? N2 C10 C11 C12 14.8(4) . . . . ? C9 C10 C11 C12 -159.4(2) . . . . ? C10 C11 C12 N3 0.7(3) . . . . ? C10 C11 C12 C13 178.7(2) . . . . ? C11 C12 C13 C14 -177.8(2) . . . . ? N3 C12 C13 C14 0.4(2) . . . . ? C11 C12 C13 C28 1.9(4) . . . . ? N3 C12 C13 C28 -179.90(19) . . . . ? C12 C13 C14 C15 0.5(2) . . . . ? C28 C13 C14 C15 -179.2(2) . . . . ? C12 C13 C14 C30 -178.9(2) . . . . ? C28 C13 C14 C30 1.5(4) . . . . ? C13 C14 C15 N3 -1.3(3) . . . . ? C30 C14 C15 N3 178.0(2) . . . . ? C13 C14 C15 C16 179.70(19) . . . . ? C30 C14 C15 C16 -1.0(4) . . . . ? N3 C15 C16 C34 -106.3(2) . . . . ? C14 C15 C16 C34 72.6(3) . . . . ? N3 C15 C16 C33 12.8(3) . . . . ? C14 C15 C16 C33 -168.3(2) . . . . ? N3 C15 C16 C32 132.1(2) . . . . ? C14 C15 C16 C32 -49.0(3) . . . . ? C4 C3 C20 C21 -78.0(3) . . . . ? C2 C3 C20 C21 101.4(2) . . . . ? C3 C4 C22 C23 105.4(2) . . . . ? C5 C4 C22 C23 -74.7(3) . . . . ? C7 C8 C24 C25 79.7(2) . . . . ? C9 C8 C24 C25 -97.2(3) . . . . ? C10 C9 C26 C27 -87.6(3) . . . . ? C8 C9 C26 C27 92.9(3) . . . . ? C14 C13 C28 C29 104.1(3) . . . . ? C12 C13 C28 C29 -75.5(3) . . . . ? C13 C14 C30 C31 -80.4(3) . . . . ? C15 C14 C30 C31 100.3(3) . . . . ? C3 C2 N1 C5 1.1(2) . . . . ? C1 C2 N1 C5 -179.83(17) . . . . ? C6 C5 N1 C2 177.1(2) . . . . ? C4 C5 N1 C2 -0.7(2) . . . . ? C9 C10 N2 C7 0.9(2) . . . . ? C11 C10 N2 C7 -174.3(2) . . . . ? C8 C7 N2 C10 0.4(2) . . . . ? C6 C7 N2 C10 -176.1(2) . . . . ? C14 C15 N3 C12 1.6(2) . . . . ? C16 C15 N3 C12 -179.37(18) . . . . ? C11 C12 N3 C15 177.1(2) . . . . ? C13 C12 N3 C15 -1.2(2) . . . . ? _diffrn_measured_fraction_theta_max 0.958 _diffrn_reflns_theta_full 26.04 _diffrn_measured_fraction_theta_full 0.958 _refine_diff_density_max 0.110 _refine_diff_density_min -0.131 _refine_diff_density_rms 0.026