# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Mei-Xiang Wang' _publ_contact_author_address ; Laboratory of Chemical Biology, Institute of Chemistry Chinese Academy of Sciences Zhong Guan Cun, Haidian District Beijing 100080 CHINA ; _publ_contact_author_email MXWANG@ICCAS.AC.CN _publ_section_title ; Synthesis and structure of nitrogen bridged calix[5]- and -[10]-pyridines and their complexation with fullerenes ; loop_ _publ_author_name 'Mei-Xiang Wang' 'Shi-Qiang Liu' 'De-Xian Wang' 'Qi-Yu Zheng' data_c5 _database_code_depnum_ccdc_archive 'CCDC 643668' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H30 N10' _chemical_formula_sum 'C30 H30 N10' _chemical_formula_weight 530.64 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 P21/c _symmetry_space_group_name_Hall -p2ybc 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 17.1305(11) _cell_length_b 12.4187(5) _cell_length_c 14.0272(2) _cell_angle_alpha 90.00 _cell_angle_beta 113.46(3) _cell_angle_gamma 90.00 _cell_volume 2737.5(2) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.288 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1120 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9919 _exptl_absorpt_correction_T_max 0.9919 _exptl_absorpt_process_details abscor _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8747 _diffrn_reflns_av_R_equivalents 0.0594 _diffrn_reflns_av_sigmaI/netI 0.0523 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4746 _reflns_number_gt 3497 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0578P)^2^+1.8942P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4746 _refine_ls_number_parameters 361 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1131 _refine_ls_R_factor_gt 0.0823 _refine_ls_wR_factor_ref 0.1877 _refine_ls_wR_factor_gt 0.1731 _refine_ls_goodness_of_fit_ref 1.170 _refine_ls_restrained_S_all 1.170 _refine_ls_shift/su_max 0.014 _refine_ls_shift/su_mean 0.003 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 0.41393(19) 0.9892(3) 0.3334(2) 0.0433(8) Uani 1 1 d . . . C2 C 0.4770(2) 0.9831(3) 0.2938(3) 0.0588(10) Uani 1 1 d . . . H2 H 0.4950 1.0440 0.2696 0.071 Uiso 1 1 calc R . . C3 C 0.5112(2) 0.8833(4) 0.2921(3) 0.0685(11) Uani 1 1 d . . . H3 H 0.5527 0.8759 0.2655 0.082 Uiso 1 1 calc R . . C4 C 0.4846(2) 0.7945(4) 0.3293(3) 0.0693(12) Uani 1 1 d . . . H4 H 0.5066 0.7266 0.3267 0.083 Uiso 1 1 calc R . . C5 C 0.4237(2) 0.8083(3) 0.3710(3) 0.0529(9) Uani 1 1 d . . . C6 C 0.3345(3) 0.7320(3) 0.4575(3) 0.0624(10) Uani 1 1 d . . . C7 C 0.3502(3) 0.6838(3) 0.5522(3) 0.0803(13) Uani 1 1 d . . . H7 H 0.4021 0.6503 0.5894 0.096 Uiso 1 1 calc R . . C8 C 0.2880(3) 0.6864(3) 0.5898(3) 0.0807(14) Uani 1 1 d . . . H8 H 0.2967 0.6527 0.6524 0.097 Uiso 1 1 calc R . . C9 C 0.2124(3) 0.7388(3) 0.5353(3) 0.0616(10) Uani 1 1 d . . . H9 H 0.1691 0.7402 0.5594 0.074 Uiso 1 1 calc R . . C10 C 0.2029(2) 0.7899(3) 0.4425(3) 0.0487(8) Uani 1 1 d . . . C11 C 0.13144(19) 0.9391(3) 0.3218(2) 0.0406(7) Uani 1 1 d . . . C12 C 0.1546(2) 0.9268(3) 0.2382(2) 0.0436(8) Uani 1 1 d . . . H12 H 0.1748 0.8615 0.2247 0.052 Uiso 1 1 calc R . . C13 C 0.1463(2) 1.0159(3) 0.1758(2) 0.0443(8) Uani 1 1 d . . . H13 H 0.1600 1.0101 0.1182 0.053 Uiso 1 1 calc R . . C14 C 0.1181(2) 1.1133(3) 0.1974(2) 0.0440(8) Uani 1 1 d . . . H14 H 0.1113 1.1729 0.1546 0.053 Uiso 1 1 calc R . . C15 C 0.10020(19) 1.1188(3) 0.2864(2) 0.0422(7) Uani 1 1 d . . . C16 C 0.1051(2) 1.3168(3) 0.3171(3) 0.0539(9) Uani 1 1 d . . . C17 C 0.0818(3) 1.4066(4) 0.3608(3) 0.0737(12) Uani 1 1 d . . . H17 H 0.0437 1.4008 0.3928 0.088 Uiso 1 1 calc R . . C18 C 0.1179(3) 1.5034(4) 0.3541(4) 0.0921(16) Uani 1 1 d . . . H18 H 0.1033 1.5645 0.3817 0.111 Uiso 1 1 calc R . . C19 C 0.1750(3) 1.5133(3) 0.3081(4) 0.0877(15) Uani 1 1 d . . . H19 H 0.1997 1.5792 0.3049 0.105 Uiso 1 1 calc R . . C20 C 0.1942(2) 1.4197(3) 0.2662(3) 0.0604(10) Uani 1 1 d . . . C21 C 0.2752(2) 1.3189(3) 0.1884(3) 0.0527(9) Uani 1 1 d . . . C22 C 0.2588(2) 1.2926(4) 0.0865(3) 0.0635(11) Uani 1 1 d . . . H22 H 0.2296 1.3397 0.0324 0.076 Uiso 1 1 calc R . . C23 C 0.2872(2) 1.1937(4) 0.0679(3) 0.0607(10) Uani 1 1 d . . . H23 H 0.2785 1.1743 0.0004 0.073 Uiso 1 1 calc R . . C24 C 0.3280(2) 1.1241(3) 0.1483(2) 0.0487(8) Uani 1 1 d . . . H24 H 0.3467 1.0572 0.1362 0.058 Uiso 1 1 calc R . . C25 C 0.34095(18) 1.1563(3) 0.2496(2) 0.0398(7) Uani 1 1 d . . . C26 C 0.4445(5) 0.6205(4) 0.4319(6) 0.150(3) Uani 1 1 d . . . H26A H 0.4185 0.5682 0.4604 0.224 Uiso 1 1 calc R . . H26B H 0.5019 0.6334 0.4803 0.224 Uiso 1 1 calc R . . H26C H 0.4448 0.5940 0.3678 0.224 Uiso 1 1 calc R . . C27 C 0.0623(2) 0.8553(3) 0.4263(3) 0.0677(11) Uani 1 1 d . . . H27A H 0.0165 0.8993 0.3809 0.102 Uiso 1 1 calc R . . H27B H 0.0845 0.8857 0.4949 0.102 Uiso 1 1 calc R . . H27C H 0.0417 0.7839 0.4285 0.102 Uiso 1 1 calc R . . C28 C 0.0183(3) 1.1993(4) 0.3793(4) 0.0783(13) Uani 1 1 d . . . H28A H 0.0000 1.1256 0.3743 0.117 Uiso 1 1 calc R . . H28B H -0.0305 1.2455 0.3518 0.117 Uiso 1 1 calc R . . H28C H 0.0509 1.2171 0.4509 0.117 Uiso 1 1 calc R . . C29 C 0.2627(4) 1.5169(4) 0.1647(5) 0.124(2) Uani 1 1 d . . . H29A H 0.3030 1.5024 0.1344 0.186 Uiso 1 1 calc R . . H29B H 0.2839 1.5738 0.2148 0.186 Uiso 1 1 calc R . . H29C H 0.2095 1.5384 0.1112 0.186 Uiso 1 1 calc R . . C30 C 0.3475(3) 1.1060(3) 0.4220(3) 0.0594(10) Uani 1 1 d . . . H30A H 0.3758 1.0555 0.4768 0.089 Uiso 1 1 calc R . . H30B H 0.2871 1.0957 0.3968 0.089 Uiso 1 1 calc R . . H30C H 0.3615 1.1780 0.4481 0.089 Uiso 1 1 calc R . . N1 N 0.39010(17) 0.9054(2) 0.3737(2) 0.0465(7) Uani 1 1 d . . . N2 N 0.3957(2) 0.7222(3) 0.4124(3) 0.0765(10) Uani 1 1 d . . . N3 N 0.2622(2) 0.7833(2) 0.4024(2) 0.0525(7) Uani 1 1 d . . . N4 N 0.13013(18) 0.8508(2) 0.3871(2) 0.0511(7) Uani 1 1 d . . . N5 N 0.10648(16) 1.0330(2) 0.3467(2) 0.0437(7) Uani 1 1 d . . . N6 N 0.07173(19) 1.2140(2) 0.3192(2) 0.0559(8) Uani 1 1 d . . . N7 N 0.15940(18) 1.3249(2) 0.2705(2) 0.0513(7) Uani 1 1 d . . . N8 N 0.2502(2) 1.4197(2) 0.2159(3) 0.0705(10) Uani 1 1 d . . . N9 N 0.31767(17) 1.2541(2) 0.2694(2) 0.0466(7) Uani 1 1 d . . . N10 N 0.37547(17) 1.0888(2) 0.3367(2) 0.0458(7) 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 C1 0.0380(17) 0.053(2) 0.0385(17) 0.0011(15) 0.0153(14) 0.0085(15) C2 0.0431(19) 0.079(3) 0.062(2) 0.005(2) 0.0282(17) 0.0078(19) C3 0.042(2) 0.094(3) 0.076(3) -0.012(2) 0.030(2) 0.013(2) C4 0.050(2) 0.073(3) 0.081(3) -0.012(2) 0.022(2) 0.025(2) C5 0.051(2) 0.052(2) 0.053(2) 0.0001(17) 0.0186(16) 0.0180(17) C6 0.082(3) 0.0335(18) 0.072(2) 0.0080(18) 0.031(2) 0.0128(19) C7 0.093(3) 0.065(3) 0.074(3) 0.026(2) 0.024(3) 0.019(2) C8 0.118(4) 0.065(3) 0.057(2) 0.025(2) 0.032(3) 0.013(3) C9 0.093(3) 0.044(2) 0.053(2) 0.0080(17) 0.034(2) -0.004(2) C10 0.063(2) 0.0350(17) 0.0487(19) -0.0020(15) 0.0230(17) -0.0113(16) C11 0.0365(16) 0.0461(18) 0.0421(17) 0.0035(14) 0.0189(14) -0.0046(14) C12 0.0455(18) 0.0482(19) 0.0419(17) -0.0006(15) 0.0224(15) -0.0013(16) C13 0.0444(18) 0.056(2) 0.0369(16) -0.0058(15) 0.0212(14) -0.0055(16) C14 0.0453(18) 0.0486(19) 0.0412(17) 0.0043(15) 0.0206(15) -0.0026(15) C15 0.0321(16) 0.0502(19) 0.0446(18) -0.0001(15) 0.0158(14) -0.0012(14) C16 0.046(2) 0.055(2) 0.053(2) -0.0018(17) 0.0117(16) 0.0124(17) C17 0.059(2) 0.077(3) 0.079(3) -0.023(2) 0.021(2) 0.016(2) C18 0.074(3) 0.063(3) 0.116(4) -0.032(3) 0.014(3) 0.016(3) C19 0.068(3) 0.042(2) 0.127(4) -0.012(2) 0.012(3) 0.003(2) C20 0.049(2) 0.041(2) 0.073(3) 0.0073(18) 0.0044(19) 0.0070(17) C21 0.0434(18) 0.047(2) 0.068(2) 0.0197(19) 0.0214(17) -0.0067(16) C22 0.045(2) 0.082(3) 0.059(2) 0.033(2) 0.0162(17) -0.005(2) C23 0.050(2) 0.091(3) 0.0429(19) 0.013(2) 0.0205(16) -0.013(2) C24 0.0415(18) 0.064(2) 0.0451(19) 0.0053(17) 0.0216(15) -0.0093(16) C25 0.0327(15) 0.0470(18) 0.0430(17) 0.0071(15) 0.0187(13) -0.0058(14) C26 0.195(7) 0.079(4) 0.229(8) 0.063(4) 0.142(6) 0.086(4) C27 0.059(2) 0.088(3) 0.066(2) 0.012(2) 0.035(2) -0.015(2) C28 0.078(3) 0.089(3) 0.094(3) 0.002(3) 0.063(3) 0.018(2) C29 0.124(5) 0.061(3) 0.191(6) 0.056(4) 0.067(5) 0.005(3) C30 0.089(3) 0.055(2) 0.0431(19) 0.0078(17) 0.0364(19) 0.019(2) N1 0.0485(16) 0.0468(16) 0.0470(15) 0.0066(13) 0.0218(13) 0.0132(13) N2 0.090(3) 0.0505(19) 0.102(3) 0.0213(19) 0.052(2) 0.0335(18) N3 0.0690(19) 0.0366(15) 0.0554(17) 0.0042(13) 0.0285(15) 0.0028(14) N4 0.0508(16) 0.0597(18) 0.0498(16) 0.0109(14) 0.0276(13) -0.0053(14) N5 0.0392(14) 0.0558(17) 0.0413(15) 0.0020(13) 0.0215(12) -0.0006(13) N6 0.0561(18) 0.0594(19) 0.0642(19) 0.0020(15) 0.0366(15) 0.0107(15) N7 0.0498(16) 0.0413(16) 0.0613(18) 0.0037(14) 0.0203(14) 0.0059(13) N8 0.066(2) 0.0439(18) 0.099(3) 0.0266(18) 0.030(2) 0.0009(16) N9 0.0441(15) 0.0442(15) 0.0523(16) 0.0109(13) 0.0202(13) -0.0019(13) N10 0.0557(17) 0.0458(16) 0.0443(15) 0.0080(12) 0.0287(13) 0.0087(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 N1 1.323(4) . ? C1 C2 1.400(5) . ? C1 N10 1.411(4) . ? C2 C3 1.375(5) . ? C2 H2 0.9300 . ? C3 C4 1.373(6) . ? C3 H3 0.9300 . ? C4 C5 1.395(5) . ? C4 H4 0.9300 . ? C5 N1 1.343(4) . ? C5 N2 1.391(5) . ? C6 N3 1.333(5) . ? C6 C7 1.382(6) . ? C6 N2 1.428(5) . ? C7 C8 1.365(6) . ? C7 H7 0.9300 . ? C8 C9 1.378(6) . ? C8 H8 0.9300 . ? C9 C10 1.398(5) . ? C9 H9 0.9300 . ? C10 N3 1.345(4) . ? C10 N4 1.400(4) . ? C11 N5 1.336(4) . ? C11 C12 1.389(4) . ? C11 N4 1.434(4) . ? C12 C13 1.382(4) . ? C12 H12 0.9300 . ? C13 C14 1.380(4) . ? C13 H13 0.9300 . ? C14 C15 1.401(4) . ? C14 H14 0.9300 . ? C15 N5 1.338(4) . ? C15 N6 1.423(4) . ? C16 N7 1.337(5) . ? C16 N6 1.403(5) . ? C16 C17 1.405(5) . ? C17 C18 1.372(7) . ? C17 H17 0.9300 . ? C18 C19 1.375(7) . ? C18 H18 0.9300 . ? C19 C20 1.399(6) . ? C19 H19 0.9300 . ? C20 N7 1.332(4) . ? C20 N8 1.399(5) . ? C21 N9 1.347(4) . ? C21 C22 1.381(5) . ? C21 N8 1.424(5) . ? C22 C23 1.384(6) . ? C22 H22 0.9300 . ? C23 C24 1.372(5) . ? C23 H23 0.9300 . ? C24 C25 1.406(4) . ? C24 H24 0.9300 . ? C25 N9 1.341(4) . ? C25 N10 1.404(4) . ? C26 N2 1.478(5) . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C27 N4 1.470(4) . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? C28 N6 1.482(5) . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? C29 N8 1.464(5) . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? C30 N10 1.471(4) . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C30 H30C 0.9600 . ? 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 N1 C1 C2 123.0(3) . . ? N1 C1 N10 116.6(3) . . ? C2 C1 N10 120.3(3) . . ? C3 C2 C1 117.1(4) . . ? C3 C2 H2 121.4 . . ? C1 C2 H2 121.4 . . ? C4 C3 C2 120.6(4) . . ? C4 C3 H3 119.7 . . ? C2 C3 H3 119.7 . . ? C3 C4 C5 118.5(4) . . ? C3 C4 H4 120.8 . . ? C5 C4 H4 120.8 . . ? N1 C5 N2 117.2(3) . . ? N1 C5 C4 121.5(4) . . ? N2 C5 C4 121.3(3) . . ? N3 C6 C7 123.0(4) . . ? N3 C6 N2 117.5(3) . . ? C7 C6 N2 119.4(4) . . ? C8 C7 C6 118.6(4) . . ? C8 C7 H7 120.7 . . ? C6 C7 H7 120.7 . . ? C7 C8 C9 120.2(4) . . ? C7 C8 H8 119.9 . . ? C9 C8 H8 119.9 . . ? C8 C9 C10 117.8(4) . . ? C8 C9 H9 121.1 . . ? C10 C9 H9 121.1 . . ? N3 C10 N4 117.1(3) . . ? N3 C10 C9 122.3(3) . . ? N4 C10 C9 120.6(3) . . ? N5 C11 C12 123.0(3) . . ? N5 C11 N4 114.4(3) . . ? C12 C11 N4 122.5(3) . . ? C13 C12 C11 117.1(3) . . ? C13 C12 H12 121.5 . . ? C11 C12 H12 121.5 . . ? C12 C13 C14 121.3(3) . . ? C12 C13 H13 119.4 . . ? C14 C13 H13 119.4 . . ? C13 C14 C15 117.3(3) . . ? C13 C14 H14 121.4 . . ? C15 C14 H14 121.4 . . ? N5 C15 C14 122.2(3) . . ? N5 C15 N6 114.2(3) . . ? C14 C15 N6 123.6(3) . . ? N7 C16 N6 116.5(3) . . ? N7 C16 C17 121.8(4) . . ? N6 C16 C17 121.6(4) . . ? C18 C17 C16 116.8(4) . . ? C18 C17 H17 121.6 . . ? C16 C17 H17 121.6 . . ? C17 C18 C19 122.4(4) . . ? C17 C18 H18 118.8 . . ? C19 C18 H18 118.8 . . ? C18 C19 C20 116.9(4) . . ? C18 C19 H19 121.5 . . ? C20 C19 H19 121.5 . . ? N7 C20 N8 115.6(3) . . ? N7 C20 C19 122.1(4) . . ? N8 C20 C19 122.3(4) . . ? N9 C21 C22 123.4(4) . . ? N9 C21 N8 114.6(3) . . ? C22 C21 N8 121.9(3) . . ? C21 C22 C23 117.6(3) . . ? C21 C22 H22 121.2 . . ? C23 C22 H22 121.2 . . ? C24 C23 C22 120.4(4) . . ? C24 C23 H23 119.8 . . ? C22 C23 H23 119.8 . . ? C23 C24 C25 118.4(4) . . ? C23 C24 H24 120.8 . . ? C25 C24 H24 120.8 . . ? N9 C25 N10 114.6(3) . . ? N9 C25 C24 121.8(3) . . ? N10 C25 C24 123.5(3) . . ? N2 C26 H26A 109.5 . . ? N2 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? N2 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? N4 C27 H27A 109.5 . . ? N4 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? N4 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? N6 C28 H28A 109.5 . . ? N6 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? N6 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? N8 C29 H29A 109.5 . . ? N8 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? N8 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? N10 C30 H30A 109.5 . . ? N10 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? N10 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C1 N1 C5 119.0(3) . . ? C5 N2 C6 123.7(3) . . ? C5 N2 C26 118.1(4) . . ? C6 N2 C26 116.9(4) . . ? C6 N3 C10 118.0(3) . . ? C10 N4 C11 122.0(3) . . ? C10 N4 C27 118.4(3) . . ? C11 N4 C27 115.1(3) . . ? C11 N5 C15 119.0(3) . . ? C16 N6 C15 123.6(3) . . ? C16 N6 C28 118.3(3) . . ? C15 N6 C28 116.7(3) . . ? C20 N7 C16 119.9(3) . . ? C20 N8 C21 118.5(3) . . ? C20 N8 C29 120.7(4) . . ? C21 N8 C29 118.2(4) . . ? C25 N9 C21 118.1(3) . . ? C25 N10 C1 122.4(3) . . ? C25 N10 C30 117.4(3) . . ? C1 N10 C30 117.5(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 N1 C1 C2 C3 3.9(5) . . . . ? N10 C1 C2 C3 -179.4(3) . . . . ? C1 C2 C3 C4 -0.8(6) . . . . ? C2 C3 C4 C5 -1.5(6) . . . . ? C3 C4 C5 N1 1.1(6) . . . . ? C3 C4 C5 N2 -178.2(4) . . . . ? N3 C6 C7 C8 1.7(7) . . . . ? N2 C6 C7 C8 -174.6(4) . . . . ? C6 C7 C8 C9 -1.8(7) . . . . ? C7 C8 C9 C10 -1.1(6) . . . . ? C8 C9 C10 N3 4.4(5) . . . . ? C8 C9 C10 N4 -175.6(3) . . . . ? N5 C11 C12 C13 -3.6(5) . . . . ? N4 C11 C12 C13 174.6(3) . . . . ? C11 C12 C13 C14 1.4(5) . . . . ? C12 C13 C14 C15 1.5(5) . . . . ? C13 C14 C15 N5 -2.6(5) . . . . ? C13 C14 C15 N6 179.2(3) . . . . ? N7 C16 C17 C18 -0.4(6) . . . . ? N6 C16 C17 C18 -179.7(4) . . . . ? C16 C17 C18 C19 -0.7(7) . . . . ? C17 C18 C19 C20 1.0(7) . . . . ? C18 C19 C20 N7 -0.2(6) . . . . ? C18 C19 C20 N8 178.9(4) . . . . ? N9 C21 C22 C23 0.6(5) . . . . ? N8 C21 C22 C23 178.7(3) . . . . ? C21 C22 C23 C24 1.7(5) . . . . ? C22 C23 C24 C25 -0.7(5) . . . . ? C23 C24 C25 N9 -2.7(4) . . . . ? C23 C24 C25 N10 174.5(3) . . . . ? C2 C1 N1 C5 -4.3(5) . . . . ? N10 C1 N1 C5 178.9(3) . . . . ? N2 C5 N1 C1 -178.9(3) . . . . ? C4 C5 N1 C1 1.7(5) . . . . ? N1 C5 N2 C6 -0.4(6) . . . . ? C4 C5 N2 C6 179.0(4) . . . . ? N1 C5 N2 C26 -166.6(5) . . . . ? C4 C5 N2 C26 12.8(7) . . . . ? N3 C6 N2 C5 50.4(6) . . . . ? C7 C6 N2 C5 -133.1(4) . . . . ? N3 C6 N2 C26 -143.2(5) . . . . ? C7 C6 N2 C26 33.3(7) . . . . ? C7 C6 N3 C10 1.5(5) . . . . ? N2 C6 N3 C10 177.8(3) . . . . ? N4 C10 N3 C6 175.4(3) . . . . ? C9 C10 N3 C6 -4.5(5) . . . . ? N3 C10 N4 C11 -27.8(4) . . . . ? C9 C10 N4 C11 152.1(3) . . . . ? N3 C10 N4 C27 177.2(3) . . . . ? C9 C10 N4 C27 -2.9(5) . . . . ? N5 C11 N4 C10 -122.5(3) . . . . ? C12 C11 N4 C10 59.2(4) . . . . ? N5 C11 N4 C27 33.3(4) . . . . ? C12 C11 N4 C27 -145.0(3) . . . . ? C12 C11 N5 C15 2.6(5) . . . . ? N4 C11 N5 C15 -175.7(3) . . . . ? C14 C15 N5 C11 0.6(4) . . . . ? N6 C15 N5 C11 179.0(3) . . . . ? N7 C16 N6 C15 7.8(5) . . . . ? C17 C16 N6 C15 -172.9(3) . . . . ? N7 C16 N6 C28 173.9(3) . . . . ? C17 C16 N6 C28 -6.8(5) . . . . ? N5 C15 N6 C16 139.8(3) . . . . ? C14 C15 N6 C16 -41.9(5) . . . . ? N5 C15 N6 C28 -26.5(4) . . . . ? C14 C15 N6 C28 151.9(3) . . . . ? N8 C20 N7 C16 180.0(3) . . . . ? C19 C20 N7 C16 -0.9(5) . . . . ? N6 C16 N7 C20 -179.4(3) . . . . ? C17 C16 N7 C20 1.2(5) . . . . ? N7 C20 N8 C21 -9.4(5) . . . . ? C19 C20 N8 C21 171.5(4) . . . . ? N7 C20 N8 C29 152.3(4) . . . . ? C19 C20 N8 C29 -26.8(6) . . . . ? N9 C21 N8 C20 -61.9(4) . . . . ? C22 C21 N8 C20 119.9(4) . . . . ? N9 C21 N8 C29 135.9(4) . . . . ? C22 C21 N8 C29 -42.3(5) . . . . ? N10 C25 N9 C21 -172.5(3) . . . . ? C24 C25 N9 C21 4.9(4) . . . . ? C22 C21 N9 C25 -3.9(5) . . . . ? N8 C21 N9 C25 177.9(3) . . . . ? N9 C25 N10 C1 -171.1(3) . . . . ? C24 C25 N10 C1 11.4(4) . . . . ? N9 C25 N10 C30 27.9(4) . . . . ? C24 C25 N10 C30 -149.5(3) . . . . ? N1 C1 N10 C25 -132.2(3) . . . . ? C2 C1 N10 C25 50.9(4) . . . . ? N1 C1 N10 C30 28.8(4) . . . . ? C2 C1 N10 C30 -148.1(3) . . . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.235 _refine_diff_density_min -0.304 _refine_diff_density_rms 0.061 # Attachment '643669.cif' data_t10 _database_code_depnum_ccdc_archive 'CCDC 643669' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C66 H72 N20 O2' _chemical_formula_weight 1177.44 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' 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' _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 17.920(4) _cell_length_b 8.3524(17) _cell_length_c 27.638(9) _cell_angle_alpha 90.00 _cell_angle_beta 124.47(2) _cell_angle_gamma 90.00 _cell_volume 3410.4(15) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5658 _cell_measurement_theta_min 1.52 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.75 _exptl_crystal_size_mid 0.54 _exptl_crystal_size_min 0.35 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.147 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1248 _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.9825 _exptl_absorpt_correction_T_max 0.9868 _exptl_absorpt_process_details ABSCOR _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku raxis Rapid IP' _diffrn_measurement_method oscillation _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 5658 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0511 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.52 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5658 _reflns_number_gt 3472 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Rapid Auto(Rigaku 2001)' _computing_cell_refinement 'Rapid Auto(Rigaku 2001)' _computing_data_reduction 'Rapid Auto(Rigaku 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.2000P)^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 constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.019(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5658 _refine_ls_number_parameters 440 _refine_ls_number_restraints 104 _refine_ls_R_factor_all 0.1594 _refine_ls_R_factor_gt 0.1221 _refine_ls_wR_factor_ref 0.3614 _refine_ls_wR_factor_gt 0.3262 _refine_ls_goodness_of_fit_ref 1.295 _refine_ls_restrained_S_all 1.316 _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 N1 N 0.5139(2) -0.1355(5) 0.36403(17) 0.0662(10) Uani 1 1 d . . . N2 N 0.3831(3) -0.0243(5) 0.34621(18) 0.0705(11) Uani 1 1 d . . . N3 N 0.2765(2) 0.1335(4) 0.34704(16) 0.0578(9) Uani 1 1 d . . . N4 N 0.1764(2) 0.3074(4) 0.34652(18) 0.0673(11) Uani 1 1 d . . . N5 N 0.0757(2) 0.4832(4) 0.34520(16) 0.0626(10) Uani 1 1 d . . . N6 N -0.0153(3) 0.6750(5) 0.34698(18) 0.0723(11) Uani 1 1 d . . . N7 N 0.0387(2) 0.8831(5) 0.41254(17) 0.0598(10) Uani 1 1 d . . . N8 N 0.0730(2) 1.1065(5) 0.47039(18) 0.0718(11) Uani 1 1 d . . . N9 N 0.2153(3) 1.1830(5) 0.54934(18) 0.0718(11) Uani 1 1 d . . . N10 N 0.3615(3) 1.2457(7) 0.62695(19) 0.0891(15) Uani 1 1 d . . . C1 C 0.5960(3) -0.1980(6) 0.4007(2) 0.0695(13) Uani 1 1 d . . . C2 C 0.6341(3) -0.2191(7) 0.4588(2) 0.0815(16) Uani 1 1 d . . . H2 H 0.6925 -0.2596 0.4832 0.098 Uiso 1 1 calc R . . C3 C 0.5836(3) -0.1784(8) 0.4810(3) 0.0879(17) Uani 1 1 d . . . H3 H 0.6075 -0.1931 0.5206 0.105 Uiso 1 1 calc R . . C4 C 0.4982(3) -0.1163(7) 0.4441(2) 0.0741(14) Uani 1 1 d . . . H4 H 0.4636 -0.0886 0.4581 0.089 Uiso 1 1 calc R . . C5 C 0.4649(3) -0.0959(6) 0.3858(2) 0.0613(12) Uani 1 1 d . . . C6 C 0.3698(4) 0.0541(9) 0.2962(3) 0.104(2) Uani 1 1 d . . . H6A H 0.4183 0.1283 0.3085 0.156 Uiso 1 1 calc R . . H6B H 0.3133 0.1109 0.2761 0.156 Uiso 1 1 calc R . . H6C H 0.3688 -0.0239 0.2704 0.156 Uiso 1 1 calc R . . C7 C 0.3154(3) -0.0104(5) 0.3582(2) 0.0595(11) Uani 1 1 d . . . C8 C 0.2908(3) -0.1373(5) 0.3775(2) 0.0691(13) Uani 1 1 d . . . H8 H 0.3197 -0.2358 0.3852 0.083 Uiso 1 1 calc R . . C9 C 0.2221(3) -0.1152(6) 0.3852(2) 0.0738(13) Uani 1 1 d . . . H9 H 0.2030 -0.2002 0.3973 0.089 Uiso 1 1 calc R . . C10 C 0.1821(3) 0.0307(6) 0.3750(2) 0.0681(13) Uani 1 1 d . . . H10 H 0.1366 0.0478 0.3811 0.082 Uiso 1 1 calc R . . C11 C 0.2107(3) 0.1525(5) 0.35556(19) 0.0559(10) Uani 1 1 d . . . C12 C 0.2372(4) 0.4389(6) 0.3607(4) 0.111(3) Uani 1 1 d . . . H12A H 0.2646 0.4698 0.4008 0.167 Uiso 1 1 calc R . . H12B H 0.2042 0.5278 0.3354 0.167 Uiso 1 1 calc R . . H12C H 0.2834 0.4068 0.3552 0.167 Uiso 1 1 calc R . . C13 C 0.0879(3) 0.3397(5) 0.3278(2) 0.0626(11) Uani 1 1 d . . . C14 C 0.0151(3) 0.2402(6) 0.2905(2) 0.0729(13) Uani 1 1 d . . . H14 H 0.0235 0.1421 0.2784 0.087 Uiso 1 1 calc R . . C15 C -0.0685(3) 0.2912(7) 0.2726(2) 0.0816(15) Uani 1 1 d . . . H15 H -0.1184 0.2278 0.2470 0.098 Uiso 1 1 calc R . . C16 C -0.0814(3) 0.4343(7) 0.2912(2) 0.0793(15) Uani 1 1 d . . . H16 H -0.1388 0.4664 0.2799 0.095 Uiso 1 1 calc R . . C17 C -0.0081(3) 0.5274(6) 0.3266(2) 0.0637(12) Uani 1 1 d . . . C18 C -0.0937(4) 0.7736(7) 0.3077(2) 0.0872(17) Uani 1 1 d . . . H18A H -0.0742 0.8782 0.3050 0.131 Uiso 1 1 calc R . . H18B H -0.1306 0.7827 0.3227 0.131 Uiso 1 1 calc R . . H18C H -0.1284 0.7253 0.2695 0.131 Uiso 1 1 calc R . . C19 C 0.0470(3) 0.7306(5) 0.4042(2) 0.0604(11) Uani 1 1 d . . . C20 C 0.1095(3) 0.6307(6) 0.4490(2) 0.0694(13) Uani 1 1 d . . . H20 H 0.1143 0.5232 0.4424 0.083 Uiso 1 1 calc R . . C21 C 0.1641(3) 0.6978(6) 0.5039(2) 0.0745(14) Uani 1 1 d . . . H21 H 0.2069 0.6346 0.5352 0.089 Uiso 1 1 calc R . . C22 C 0.1565(4) 0.8564(7) 0.5131(2) 0.0787(14) Uani 1 1 d . . . H22 H 0.1942 0.9023 0.5501 0.094 Uiso 1 1 calc R . . C23 C 0.0918(3) 0.9450(5) 0.4662(2) 0.0619(12) Uani 1 1 d . . . C24 C -0.0134(4) 1.1726(7) 0.4233(2) 0.0866(16) Uani 1 1 d . . . H24A H -0.0147 1.2853 0.4297 0.130 Uiso 1 1 calc R . . H24B H -0.0615 1.1203 0.4228 0.130 Uiso 1 1 calc R . . H24C H -0.0209 1.1559 0.3864 0.130 Uiso 1 1 calc R . . C25 C 0.1253(3) 1.1979(6) 0.5207(2) 0.0656(12) Uani 1 1 d . . . C26 C 0.0860(3) 1.3023(6) 0.5383(2) 0.0743(14) Uani 1 1 d . . . H26 H 0.0234 1.3121 0.5174 0.089 Uiso 1 1 calc R . . C27 C 0.1419(4) 1.3915(7) 0.5875(3) 0.0820(16) Uani 1 1 d . . . H27 H 0.1171 1.4623 0.6007 0.098 Uiso 1 1 calc R . . C28 C 0.2345(4) 1.3779(7) 0.6178(2) 0.0776(14) Uani 1 1 d . . . H28 H 0.2727 1.4398 0.6509 0.093 Uiso 1 1 calc R . . C29 C 0.2688(3) 1.2705(7) 0.5977(2) 0.0732(14) Uani 1 1 d . . . C30 C 0.4189(5) 1.2832(15) 0.6894(3) 0.165(5) Uani 1 1 d . . . H30A H 0.4423 1.3899 0.6946 0.247 Uiso 1 1 calc R . . H30B H 0.4682 1.2086 0.7089 0.247 Uiso 1 1 calc R . . H30C H 0.3839 1.2760 0.7057 0.247 Uiso 1 1 calc R . . O1 O 0.5710(11) 0.151(2) 0.8736(7) 0.186(6) Uani 0.431(9) 1 d PDU A 1 C31 C 0.6136(13) 0.231(3) 0.9684(8) 0.145(7) Uani 0.431(9) 1 d PDU A 1 H31A H 0.6572 0.2933 0.9670 0.218 Uiso 0.431(9) 1 calc PR A 1 H31B H 0.6444 0.1525 0.9991 0.218 Uiso 0.431(9) 1 calc PR A 1 H31C H 0.5784 0.2993 0.9760 0.218 Uiso 0.431(9) 1 calc PR A 1 C32 C 0.5525(9) 0.1475(14) 0.9109(7) 0.161(7) Uani 0.431(9) 1 d PDU A 1 C33 C 0.4700(11) 0.061(2) 0.8987(9) 0.143(6) Uani 0.431(9) 1 d PDU A 1 H33A H 0.4312 0.0362 0.8576 0.215 Uiso 0.431(9) 1 calc PR A 1 H33B H 0.4381 0.1285 0.9094 0.215 Uiso 0.431(9) 1 calc PR A 1 H33C H 0.4879 -0.0358 0.9212 0.215 Uiso 0.431(9) 1 calc PR A 1 O2 O 0.7621(9) 0.2433(16) 0.8084(6) 0.198(6) Uani 0.569(9) 1 d PDU A 2 C34 C 0.6875(14) 0.472(2) 0.7500(9) 0.221(9) Uani 0.569(9) 1 d PDU A 2 H34A H 0.7030 0.4281 0.7246 0.331 Uiso 0.569(9) 1 calc PR A 2 H34B H 0.7257 0.5621 0.7708 0.331 Uiso 0.569(9) 1 calc PR A 2 H34C H 0.6254 0.5055 0.7270 0.331 Uiso 0.569(9) 1 calc PR A 2 C35 C 0.7011(8) 0.3447(17) 0.7938(5) 0.184(6) Uani 0.569(9) 1 d PDU A 2 C36 C 0.6448(8) 0.3387(18) 0.8189(5) 0.114(4) Uani 0.569(9) 1 d PDU A 2 H36A H 0.6627 0.2480 0.8446 0.171 Uiso 0.569(9) 1 calc PR A 2 H36B H 0.5819 0.3293 0.7875 0.171 Uiso 0.569(9) 1 calc PR A 2 H36C H 0.6541 0.4351 0.8406 0.171 Uiso 0.569(9) 1 calc PRU A 2 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 N1 0.056(2) 0.075(2) 0.074(2) -0.0132(19) 0.0412(19) -0.0015(18) N2 0.061(2) 0.081(3) 0.082(3) 0.010(2) 0.048(2) 0.018(2) N3 0.0513(18) 0.053(2) 0.069(2) 0.0021(16) 0.0343(17) 0.0016(16) N4 0.058(2) 0.052(2) 0.100(3) 0.0002(19) 0.050(2) 0.0045(17) N5 0.057(2) 0.060(2) 0.073(2) 0.0057(18) 0.0379(19) 0.0081(17) N6 0.061(2) 0.077(3) 0.072(2) 0.006(2) 0.033(2) 0.022(2) N7 0.0518(19) 0.066(2) 0.070(2) 0.0113(18) 0.0393(18) 0.0093(17) N8 0.057(2) 0.072(3) 0.081(3) 0.000(2) 0.036(2) 0.0130(19) N9 0.057(2) 0.086(3) 0.080(3) -0.003(2) 0.043(2) 0.011(2) N10 0.055(2) 0.142(4) 0.071(3) -0.024(3) 0.036(2) 0.007(2) C1 0.049(2) 0.085(3) 0.078(3) -0.016(3) 0.038(2) 0.004(2) C2 0.053(2) 0.119(5) 0.073(3) -0.003(3) 0.035(2) 0.015(3) C3 0.056(3) 0.129(5) 0.079(3) -0.003(3) 0.039(3) 0.009(3) C4 0.057(3) 0.101(4) 0.073(3) -0.006(3) 0.042(2) 0.011(3) C5 0.049(2) 0.066(3) 0.073(3) -0.008(2) 0.037(2) 0.002(2) C6 0.096(4) 0.140(6) 0.102(4) 0.038(4) 0.071(4) 0.032(4) C7 0.052(2) 0.059(3) 0.071(3) -0.002(2) 0.037(2) 0.004(2) C8 0.063(3) 0.048(2) 0.098(4) 0.001(2) 0.047(3) 0.002(2) C9 0.066(3) 0.062(3) 0.098(4) 0.013(3) 0.049(3) 0.003(2) C10 0.061(3) 0.068(3) 0.089(3) 0.008(2) 0.050(3) 0.004(2) C11 0.049(2) 0.053(2) 0.071(3) -0.0023(19) 0.037(2) 0.0002(18) C12 0.081(4) 0.053(3) 0.215(8) 0.000(4) 0.093(5) 0.001(3) C13 0.060(2) 0.059(3) 0.074(3) 0.008(2) 0.041(2) 0.007(2) C14 0.060(3) 0.071(3) 0.081(3) -0.003(2) 0.036(2) 0.006(2) C15 0.059(3) 0.086(4) 0.079(3) -0.005(3) 0.026(3) -0.001(3) C16 0.057(3) 0.085(4) 0.084(3) 0.001(3) 0.033(3) 0.016(3) C17 0.055(2) 0.067(3) 0.068(3) 0.010(2) 0.034(2) 0.019(2) C18 0.075(3) 0.094(4) 0.076(3) 0.007(3) 0.033(3) 0.033(3) C19 0.056(2) 0.066(3) 0.066(3) 0.010(2) 0.039(2) 0.011(2) C20 0.065(3) 0.069(3) 0.074(3) 0.011(2) 0.039(3) 0.011(2) C21 0.064(3) 0.076(3) 0.071(3) 0.014(3) 0.031(2) 0.015(3) C22 0.077(3) 0.079(3) 0.073(3) 0.007(3) 0.038(3) 0.015(3) C23 0.051(2) 0.063(3) 0.073(3) 0.012(2) 0.036(2) 0.010(2) C24 0.078(3) 0.082(3) 0.085(4) 0.007(3) 0.037(3) 0.028(3) C25 0.058(2) 0.070(3) 0.079(3) 0.012(2) 0.045(2) 0.014(2) C26 0.060(3) 0.076(3) 0.099(4) 0.002(3) 0.053(3) 0.012(2) C27 0.084(3) 0.083(4) 0.104(4) 0.002(3) 0.068(3) 0.019(3) C28 0.076(3) 0.080(3) 0.089(3) -0.008(3) 0.054(3) 0.004(3) C29 0.065(3) 0.088(3) 0.078(3) 0.000(3) 0.048(3) 0.014(3) C30 0.091(5) 0.299(13) 0.091(5) -0.066(6) 0.044(4) 0.032(6) O1 0.195(10) 0.211(10) 0.171(9) -0.007(7) 0.116(7) 0.020(7) C31 0.122(9) 0.150(10) 0.158(10) -0.031(7) 0.075(7) 0.012(7) C32 0.152(9) 0.154(9) 0.169(9) 0.003(7) 0.085(7) 0.022(7) C33 0.101(8) 0.128(9) 0.178(10) 0.030(7) 0.066(7) 0.004(7) O2 0.171(8) 0.171(8) 0.212(9) -0.005(7) 0.084(6) 0.023(6) C34 0.213(11) 0.232(12) 0.228(11) 0.011(8) 0.132(8) -0.014(8) C35 0.172(9) 0.173(9) 0.194(9) -0.005(7) 0.096(7) 0.016(7) C36 0.110(6) 0.139(7) 0.095(6) -0.016(5) 0.060(5) -0.019(6) _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 N1 C1 1.333(6) . ? N1 C5 1.357(5) . ? N2 C5 1.375(6) . ? N2 C6 1.422(7) . ? N2 C7 1.431(6) . ? N3 C7 1.335(6) . ? N3 C11 1.336(5) . ? N4 C13 1.387(6) . ? N4 C11 1.393(6) . ? N4 C12 1.436(6) . ? N5 C17 1.334(5) . ? N5 C13 1.354(6) . ? N6 C17 1.392(6) . ? N6 C19 1.402(6) . ? N6 C18 1.451(6) . ? N7 C19 1.318(6) . ? N7 C23 1.333(6) . ? N8 C25 1.385(6) . ? N8 C23 1.410(6) . ? N8 C24 1.454(6) . ? N9 C29 1.337(7) . ? N9 C25 1.341(6) . ? N10 C29 1.391(6) . ? N10 C1 1.406(6) 3_666 ? N10 C30 1.458(8) . ? C1 C2 1.355(7) . ? C1 N10 1.406(6) 3_666 ? C2 C3 1.395(7) . ? C2 H2 0.9300 . ? C3 C4 1.372(7) . ? C3 H3 0.9300 . ? C4 C5 1.375(7) . ? C4 H4 0.9300 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 C8 1.367(7) . ? C8 C9 1.375(7) . ? C8 H8 0.9300 . ? C9 C10 1.360(7) . ? C9 H9 0.9300 . ? C10 C11 1.379(6) . ? C10 H10 0.9300 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 C14 1.390(7) . ? C14 C15 1.353(7) . ? C14 H14 0.9300 . ? C15 C16 1.371(8) . ? C15 H15 0.9300 . ? C16 C17 1.354(7) . ? C16 H16 0.9300 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 C20 1.383(6) . ? C20 C21 1.376(7) . ? C20 H20 0.9300 . ? C21 C22 1.371(8) . ? C21 H21 0.9300 . ? C22 C23 1.368(6) . ? C22 H22 0.9300 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 C26 1.371(7) . ? C26 C27 1.366(8) . ? C26 H26 0.9300 . ? C27 C28 1.376(7) . ? C27 H27 0.9300 . ? C28 C29 1.371(7) . ? C28 H28 0.9300 . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C30 H30C 0.9600 . ? O1 C32 1.251(10) . ? C31 C32 1.495(10) . ? C31 H31A 0.9600 . ? C31 H31B 0.9600 . ? C31 H31C 0.9600 . ? C32 C33 1.501(10) . ? C33 H33A 0.9600 . ? C33 H33B 0.9600 . ? C33 H33C 0.9600 . ? O2 C35 1.256(9) . ? C34 C35 1.523(10) . ? C34 H34A 0.9600 . ? C34 H34B 0.9600 . ? C34 H34C 0.9600 . ? C35 C36 1.516(9) . ? C36 H36A 0.9600 . ? C36 H36B 0.9600 . ? C36 H36C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C5 118.2(4) . . ? C5 N2 C6 119.4(4) . . ? C5 N2 C7 120.9(4) . . ? C6 N2 C7 119.3(4) . . ? C7 N3 C11 117.7(4) . . ? C13 N4 C11 122.9(4) . . ? C13 N4 C12 118.9(4) . . ? C11 N4 C12 118.1(4) . . ? C17 N5 C13 118.7(4) . . ? C17 N6 C19 123.6(4) . . ? C17 N6 C18 118.2(4) . . ? C19 N6 C18 118.2(4) . . ? C19 N7 C23 119.3(4) . . ? C25 N8 C23 123.5(4) . . ? C25 N8 C24 117.5(4) . . ? C23 N8 C24 118.2(4) . . ? C29 N9 C25 118.9(4) . . ? C29 N10 C1 124.1(4) . 3_666 ? C29 N10 C30 117.8(5) . . ? C1 N10 C30 117.9(5) 3_666 . ? N1 C1 C2 123.4(4) . . ? N1 C1 N10 113.7(4) . 3_666 ? C2 C1 N10 122.8(4) . 3_666 ? C1 C2 C3 118.3(5) . . ? C1 C2 H2 120.9 . . ? C3 C2 H2 120.9 . . ? C4 C3 C2 119.5(5) . . ? C4 C3 H3 120.3 . . ? C2 C3 H3 120.3 . . ? C3 C4 C5 118.8(5) . . ? C3 C4 H4 120.6 . . ? C5 C4 H4 120.6 . . ? N1 C5 N2 114.8(4) . . ? N1 C5 C4 121.9(4) . . ? N2 C5 C4 123.1(4) . . ? N2 C6 H6A 109.5 . . ? N2 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N2 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N3 C7 C8 123.1(4) . . ? N3 C7 N2 114.9(4) . . ? C8 C7 N2 122.0(4) . . ? C7 C8 C9 118.1(4) . . ? C7 C8 H8 121.0 . . ? C9 C8 H8 121.0 . . ? C10 C9 C8 120.2(5) . . ? C10 C9 H9 119.9 . . ? C8 C9 H9 119.9 . . ? C9 C10 C11 118.2(4) . . ? C9 C10 H10 120.9 . . ? C11 C10 H10 120.9 . . ? N3 C11 C10 122.8(4) . . ? N3 C11 N4 115.0(4) . . ? C10 C11 N4 122.1(4) . . ? N4 C12 H12A 109.5 . . ? N4 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N4 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N5 C13 N4 114.8(4) . . ? N5 C13 C14 121.2(4) . . ? N4 C13 C14 123.8(4) . . ? C15 C14 C13 117.6(5) . . ? C15 C14 H14 121.2 . . ? C13 C14 H14 121.2 . . ? C14 C15 C16 121.6(5) . . ? C14 C15 H15 119.2 . . ? C16 C15 H15 119.2 . . ? C17 C16 C15 118.1(5) . . ? C17 C16 H16 121.0 . . ? C15 C16 H16 121.0 . . ? N5 C17 C16 122.7(4) . . ? N5 C17 N6 115.6(4) . . ? C16 C17 N6 121.8(4) . . ? N6 C18 H18A 109.5 . . ? N6 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? N6 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N7 C19 C20 122.7(5) . . ? N7 C19 N6 114.9(4) . . ? C20 C19 N6 122.3(4) . . ? C21 C20 C19 116.8(5) . . ? C21 C20 H20 121.6 . . ? C19 C20 H20 121.6 . . ? C22 C21 C20 121.1(5) . . ? C22 C21 H21 119.5 . . ? C20 C21 H21 119.5 . . ? C23 C22 C21 117.8(5) . . ? C23 C22 H22 121.1 . . ? C21 C22 H22 121.1 . . ? N7 C23 C22 122.2(4) . . ? N7 C23 N8 114.2(4) . . ? C22 C23 N8 123.6(5) . . ? N8 C24 H24A 109.5 . . ? N8 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? N8 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? N9 C25 C26 122.5(5) . . ? N9 C25 N8 116.4(4) . . ? C26 C25 N8 121.0(4) . . ? C27 C26 C25 117.7(5) . . ? C27 C26 H26 121.1 . . ? C25 C26 H26 121.1 . . ? C26 C27 C28 120.9(5) . . ? C26 C27 H27 119.5 . . ? C28 C27 H27 119.5 . . ? C29 C28 C27 118.1(5) . . ? C29 C28 H28 121.0 . . ? C27 C28 H28 121.0 . . ? N9 C29 C28 122.0(5) . . ? N9 C29 N10 116.5(4) . . ? C28 C29 N10 121.6(5) . . ? N10 C30 H30A 109.5 . . ? N10 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? N10 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C32 C31 H31A 109.5 . . ? C32 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C32 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? O1 C32 C31 119.3(12) . . ? O1 C32 C33 120.9(13) . . ? C31 C32 C33 119.8(16) . . ? 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 . . ? C35 C34 H34A 109.5 . . ? C35 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C35 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? O2 C35 C36 121.0(12) . . ? O2 C35 C34 116.4(11) . . ? C36 C35 C34 122.7(14) . . ? C35 C36 H36A 109.5 . . ? C35 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C35 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 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 C5 N1 C1 C2 -2.2(8) . . . . ? C5 N1 C1 N10 175.6(4) . . . 3_666 ? N1 C1 C2 C3 2.3(9) . . . . ? N10 C1 C2 C3 -175.3(6) 3_666 . . . ? C1 C2 C3 C4 -1.1(9) . . . . ? C2 C3 C4 C5 0.0(9) . . . . ? C1 N1 C5 N2 176.6(4) . . . . ? C1 N1 C5 C4 1.0(7) . . . . ? C6 N2 C5 N1 -22.6(7) . . . . ? C7 N2 C5 N1 165.1(4) . . . . ? C6 N2 C5 C4 152.9(6) . . . . ? C7 N2 C5 C4 -19.3(7) . . . . ? C3 C4 C5 N1 0.1(8) . . . . ? C3 C4 C5 N2 -175.2(5) . . . . ? C11 N3 C7 C8 0.2(7) . . . . ? C11 N3 C7 N2 177.9(4) . . . . ? C5 N2 C7 N3 134.1(5) . . . . ? C6 N2 C7 N3 -38.1(7) . . . . ? C5 N2 C7 C8 -48.1(6) . . . . ? C6 N2 C7 C8 139.6(6) . . . . ? N3 C7 C8 C9 0.7(7) . . . . ? N2 C7 C8 C9 -176.9(4) . . . . ? C7 C8 C9 C10 -1.6(8) . . . . ? C8 C9 C10 C11 1.7(8) . . . . ? C7 N3 C11 C10 -0.1(6) . . . . ? C7 N3 C11 N4 176.4(4) . . . . ? C9 C10 C11 N3 -0.9(7) . . . . ? C9 C10 C11 N4 -177.1(5) . . . . ? C13 N4 C11 N3 150.7(4) . . . . ? C12 N4 C11 N3 -33.1(7) . . . . ? C13 N4 C11 C10 -32.8(7) . . . . ? C12 N4 C11 C10 143.4(6) . . . . ? C17 N5 C13 N4 176.5(4) . . . . ? C17 N5 C13 C14 0.9(7) . . . . ? C11 N4 C13 N5 152.1(4) . . . . ? C12 N4 C13 N5 -24.1(7) . . . . ? C11 N4 C13 C14 -32.4(7) . . . . ? C12 N4 C13 C14 151.4(6) . . . . ? N5 C13 C14 C15 -0.5(8) . . . . ? N4 C13 C14 C15 -175.7(5) . . . . ? C13 C14 C15 C16 -1.3(9) . . . . ? C14 C15 C16 C17 2.6(9) . . . . ? C13 N5 C17 C16 0.4(7) . . . . ? C13 N5 C17 N6 179.0(4) . . . . ? C15 C16 C17 N5 -2.1(8) . . . . ? C15 C16 C17 N6 179.4(5) . . . . ? C19 N6 C17 N5 -38.7(7) . . . . ? C18 N6 C17 N5 144.1(5) . . . . ? C19 N6 C17 C16 139.9(5) . . . . ? C18 N6 C17 C16 -37.3(7) . . . . ? C23 N7 C19 C20 -0.6(7) . . . . ? C23 N7 C19 N6 176.4(4) . . . . ? C17 N6 C19 N7 168.2(4) . . . . ? C18 N6 C19 N7 -14.6(7) . . . . ? C17 N6 C19 C20 -14.8(7) . . . . ? C18 N6 C19 C20 162.4(5) . . . . ? N7 C19 C20 C21 -0.2(7) . . . . ? N6 C19 C20 C21 -176.9(4) . . . . ? C19 C20 C21 C22 -0.1(8) . . . . ? C20 C21 C22 C23 1.1(8) . . . . ? C19 N7 C23 C22 1.6(7) . . . . ? C19 N7 C23 N8 -176.4(4) . . . . ? C21 C22 C23 N7 -1.9(8) . . . . ? C21 C22 C23 N8 175.9(5) . . . . ? C25 N8 C23 N7 -173.8(4) . . . . ? C24 N8 C23 N7 16.9(6) . . . . ? C25 N8 C23 C22 8.2(7) . . . . ? C24 N8 C23 C22 -161.1(5) . . . . ? C29 N9 C25 C26 1.6(8) . . . . ? C29 N9 C25 N8 179.0(5) . . . . ? C23 N8 C25 N9 42.7(7) . . . . ? C24 N8 C25 N9 -148.0(5) . . . . ? C23 N8 C25 C26 -139.9(5) . . . . ? C24 N8 C25 C26 29.4(7) . . . . ? N9 C25 C26 C27 -1.1(8) . . . . ? N8 C25 C26 C27 -178.3(5) . . . . ? C25 C26 C27 C28 0.8(8) . . . . ? C26 C27 C28 C29 -1.0(9) . . . . ? C25 N9 C29 C28 -1.9(8) . . . . ? C25 N9 C29 N10 177.5(5) . . . . ? C27 C28 C29 N9 1.6(9) . . . . ? C27 C28 C29 N10 -177.8(5) . . . . ? C1 N10 C29 N9 29.6(8) 3_666 . . . ? C30 N10 C29 N9 -155.2(7) . . . . ? C1 N10 C29 C28 -151.0(6) 3_666 . . . ? C30 N10 C29 C28 24.2(10) . . . . ? _diffrn_measured_fraction_theta_max 0.942 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.942 _refine_diff_density_max 0.893 _refine_diff_density_min -0.462 _refine_diff_density_rms 0.134