# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_BPNIA _database_code_depnum_ccdc_archive 'CCDC 883025' #TrackingRef '11374_web_deposit_cif_file_0_YupingZhang_1337328118.BPNIA.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C44 H39 N7 O6' _chemical_formula_weight 761.82 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 triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.0684(18) _cell_length_b 14.326(3) _cell_length_c 15.214(3) _cell_angle_alpha 83.83(3) _cell_angle_beta 89.85(3) _cell_angle_gamma 89.66(3) _cell_volume 1965.0(7) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.288 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9627 _exptl_absorpt_correction_T_max 0.9889 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _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 18724 _diffrn_reflns_av_R_equivalents 0.0536 _diffrn_reflns_av_sigmaI/netI 0.0841 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.03 _diffrn_reflns_theta_max 27.48 _reflns_number_total 8702 _reflns_number_gt 4128 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.1179P)^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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8702 _refine_ls_number_parameters 543 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.1633 _refine_ls_R_factor_gt 0.0778 _refine_ls_wR_factor_ref 0.2352 _refine_ls_wR_factor_gt 0.1998 _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_restrained_S_all 1.034 _refine_ls_shift/su_max 0.079 _refine_ls_shift/su_mean 0.012 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 H102 H 1.426(4) 0.121(3) 0.952(2) 0.074(11) Uiso 1 1 d . . . H103 H -0.377(3) 0.096(2) 0.544(2) 0.050(9) Uiso 1 1 d . . . H101 H 0.172(4) -0.156(3) 0.670(2) 0.078(12) Uiso 1 1 d . . . H100 H 0.774(3) 0.000(2) 0.821(2) 0.041(10) Uiso 1 1 d . . . O2 O 0.3918(3) -0.41864(17) 0.7549(2) 0.0903(10) Uani 1 1 d . . . O3 O 0.9214(2) -0.17870(15) 0.84427(17) 0.0650(7) Uani 1 1 d . . . O4 O 0.3769(2) 0.01686(16) 0.6490(2) 0.0771(9) Uani 1 1 d . . . N1 N 1.1536(3) 0.3725(2) 0.9799(3) 0.0930(13) Uani 1 1 d . . . N4 N -0.1285(4) 0.3470(2) 0.5616(3) 0.0942(12) Uani 1 1 d . . . N2 N 0.8357(3) -0.02990(19) 0.83486(19) 0.0480(7) Uani 1 1 d . . . N3 N 0.1953(3) -0.09192(19) 0.66289(17) 0.0461(6) Uani 1 1 d . . . N10 N 0.5112(3) -0.3886(2) 0.7741(2) 0.0639(8) Uani 1 1 d . . . C4 C 1.5051(3) 0.2825(2) 0.9962(2) 0.0465(8) Uani 1 1 d . . . C5 C 1.6139(3) 0.2240(3) 1.0339(3) 0.0618(10) Uani 1 1 d . . . H40 H 1.5939 0.1607 1.0492 0.074 Uiso 1 1 calc R . . C41 C 1.7522(4) 0.2581(3) 1.0492(3) 0.0751(12) Uani 1 1 d . . . H41 H 1.8247 0.2176 1.0742 0.090 Uiso 1 1 calc R . . C1 C 1.7837(4) 0.3504(3) 1.0281(3) 0.0738(12) Uani 1 1 d . . . H42 H 1.8770 0.3730 1.0391 0.089 Uiso 1 1 calc R . . C2 C 1.6777(4) 0.4095(3) 0.9905(3) 0.0734(12) Uani 1 1 d . . . H43 H 1.6993 0.4725 0.9749 0.088 Uiso 1 1 calc R . . C3 C 1.5388(3) 0.3764(2) 0.9756(3) 0.0627(10) Uani 1 1 d . . . H44 H 1.4666 0.4177 0.9513 0.075 Uiso 1 1 calc R . . C6 C 1.3562(3) 0.2467(2) 0.9754(2) 0.0476(8) Uani 1 1 d . . . C7 C 1.2404(4) 0.3152(2) 0.9760(3) 0.0609(10) Uani 1 1 d . . . C8 C 1.3336(3) 0.1603(2) 0.9537(2) 0.0499(8) Uani 1 1 d . . . C9 C 1.1999(3) 0.1140(2) 0.9262(2) 0.0464(7) Uani 1 1 d . . . C10 C 1.2183(3) 0.0288(2) 0.8922(2) 0.0523(8) Uani 1 1 d . . . H49 H 1.3129 0.0039 0.8895 0.063 Uiso 1 1 calc R . . C11 C 1.1021(3) -0.0206(2) 0.8622(2) 0.0526(8) Uani 1 1 d . . . H50 H 1.1189 -0.0776 0.8397 0.063 Uiso 1 1 calc R . . C13 C 0.9395(3) 0.0990(2) 0.9005(3) 0.0589(9) Uani 1 1 d . . . H51 H 0.8447 0.1234 0.9042 0.071 Uiso 1 1 calc R . . C14 C 1.0567(3) 0.1478(2) 0.9299(3) 0.0617(10) Uani 1 1 d . . . H52 H 1.0394 0.2046 0.9526 0.074 Uiso 1 1 calc R . . C12 C 0.9594(3) 0.0154(2) 0.8660(2) 0.0431(7) Uani 1 1 d . . . C15 C 0.8240(3) -0.1221(2) 0.8242(2) 0.0449(7) Uani 1 1 d . . . C16 C 0.6820(3) -0.1550(2) 0.7868(2) 0.0430(7) Uani 1 1 d . . . C18 C 0.6618(3) -0.2516(2) 0.7947(2) 0.0477(8) Uani 1 1 d . . . H56 H 0.7333 -0.2921 0.8212 0.057 Uiso 1 1 calc R . . C17 C 0.5744(3) -0.0969(2) 0.7457(2) 0.0443(7) Uani 1 1 d . . . H57 H 0.5879 -0.0322 0.7397 0.053 Uiso 1 1 calc R . . C20 C 0.4246(3) -0.2299(2) 0.7222(2) 0.0468(8) Uani 1 1 d . . . H58 H 0.3389 -0.2554 0.7016 0.056 Uiso 1 1 calc R . . C19 C 0.5325(3) -0.2865(2) 0.7622(2) 0.0465(8) Uani 1 1 d . . . C21 C 0.4460(3) -0.1339(2) 0.7131(2) 0.0432(7) Uani 1 1 d . . . C22 C 0.3360(3) -0.0630(2) 0.6713(2) 0.0495(8) Uani 1 1 d . . . C23 C 0.0742(3) -0.0323(2) 0.6363(2) 0.0447(7) Uani 1 1 d . . . C24 C 0.0727(4) 0.0625(2) 0.6457(2) 0.0560(9) Uani 1 1 d . . . H63 H 0.1549 0.0901 0.6684 0.067 Uiso 1 1 calc R . . C25 C -0.0494(3) 0.1162(2) 0.6218(2) 0.0577(9) Uani 1 1 d . . . H64 H -0.0489 0.1796 0.6298 0.069 Uiso 1 1 calc R . . C26 C -0.1749(3) 0.0784(2) 0.5855(2) 0.0464(7) Uani 1 1 d . . . C27 C -0.1722(3) -0.0176(2) 0.5810(2) 0.0507(8) Uani 1 1 d . . . H66 H -0.2557 -0.0461 0.5610 0.061 Uiso 1 1 calc R . . C28 C -0.0505(3) -0.0726(2) 0.6050(2) 0.0489(8) Uani 1 1 d . . . H67 H -0.0524 -0.1367 0.6002 0.059 Uiso 1 1 calc R . . C29 C -0.3052(3) 0.1318(2) 0.5554(2) 0.0488(8) Uani 1 1 d . . . C30 C -0.3289(3) 0.2245(2) 0.5393(2) 0.0473(8) Uani 1 1 d . . . C70 C -0.2139(4) 0.2907(2) 0.5519(2) 0.0623(10) Uani 1 1 d . . . C31 C -0.4721(3) 0.2687(2) 0.5082(2) 0.0481(8) Uani 1 1 d . . . C36 C -0.6025(3) 0.2208(2) 0.5209(3) 0.0645(10) Uani 1 1 d . . . H72 H -0.6016 0.1592 0.5475 0.077 Uiso 1 1 calc R . . C35 C -0.7352(4) 0.2629(3) 0.4946(3) 0.0805(13) Uani 1 1 d . . . H73 H -0.8224 0.2292 0.5030 0.097 Uiso 1 1 calc R . . C34 C -0.7385(5) 0.3539(3) 0.4563(3) 0.0844(13) Uani 1 1 d . . . H74 H -0.8277 0.3825 0.4391 0.101 Uiso 1 1 calc R . . C33 C -0.6089(4) 0.4025(3) 0.4434(3) 0.0807(12) Uani 1 1 d . . . H75 H -0.6101 0.4641 0.4168 0.097 Uiso 1 1 calc R . . C32 C -0.4762(4) 0.3601(2) 0.4700(3) 0.0656(10) Uani 1 1 d . . . H76 H -0.3890 0.3939 0.4620 0.079 Uiso 1 1 calc R . . O5 O 0.8990(3) 0.28688(18) 0.3347(2) 0.0815(9) Uani 1 1 d . . . N5 N 0.9634(3) 0.4321(2) 0.2745(2) 0.0673(9) Uani 1 1 d . . . C43 C 1.0215(6) 0.4908(4) 0.1987(4) 0.124(2) Uani 1 1 d . . . H43A H 1.0531 0.4520 0.1545 0.186 Uiso 1 1 calc R . . H43B H 1.1037 0.5260 0.2168 0.186 Uiso 1 1 calc R . . H43C H 0.9460 0.5333 0.1746 0.186 Uiso 1 1 calc R . . C40 C 0.9050(5) 0.4791(3) 0.3475(4) 0.0935(15) Uani 1 1 d . . . H40A H 0.8115 0.5074 0.3309 0.140 Uiso 1 1 calc R . . H40B H 0.9726 0.5267 0.3613 0.140 Uiso 1 1 calc R . . H40C H 0.8923 0.4340 0.3983 0.140 Uiso 1 1 calc R . . C42 C 0.9526(4) 0.3406(3) 0.2747(3) 0.0736(12) Uani 1 1 d . . . H42A H 0.9884 0.3144 0.2255 0.088 Uiso 1 1 calc R . . O1 O 0.594(2) -0.4401(17) 0.8087(18) 0.078(5) Uani 0.50 1 d P . . O1' O 0.632(3) -0.4357(17) 0.795(2) 0.093(7) Uani 0.50 1 d P . . O6 O 0.3837(3) 0.8813(2) 0.2024(2) 0.0865(9) Uani 1 1 d . . . N6 N 0.4620(4) 0.7340(2) 0.2438(2) 0.0856(11) Uani 1 1 d . . . C39 C 0.4729(5) 0.8244(3) 0.2308(3) 0.0830(12) Uani 1 1 d . . . H39 H 0.5633 0.8485 0.2458 0.100 Uiso 1 1 calc R . . C38 C 0.3164(7) 0.6930(4) 0.2245(4) 0.140(2) Uani 1 1 d U . . H38A H 0.2416 0.7408 0.2230 0.211 Uiso 1 1 calc R . . H38B H 0.2931 0.6433 0.2697 0.211 Uiso 1 1 calc R . . H38C H 0.3207 0.6685 0.1682 0.211 Uiso 1 1 calc R . . C37 C 0.5752(9) 0.6698(5) 0.2715(4) 0.155(3) Uani 1 1 d U . . H37A H 0.6632 0.7036 0.2825 0.232 Uiso 1 1 calc R . . H37B H 0.5941 0.6296 0.2261 0.232 Uiso 1 1 calc R . . H37C H 0.5455 0.6326 0.3247 0.232 Uiso 1 1 calc R . . 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 O2 0.0738(17) 0.0442(14) 0.152(3) -0.0057(15) -0.0380(17) -0.0193(13) O3 0.0559(13) 0.0408(13) 0.099(2) -0.0118(12) -0.0286(12) 0.0024(11) O4 0.0531(13) 0.0411(14) 0.131(2) 0.0204(14) -0.0214(14) -0.0096(11) N1 0.0474(17) 0.052(2) 0.180(4) -0.014(2) -0.014(2) 0.0000(16) N4 0.088(2) 0.064(2) 0.129(3) 0.002(2) -0.038(2) -0.025(2) N2 0.0458(15) 0.0382(16) 0.0610(19) -0.0104(13) -0.0148(13) 0.0010(13) N3 0.0425(14) 0.0381(15) 0.0573(18) -0.0036(12) -0.0089(11) -0.0019(12) N10 0.0670(19) 0.0366(16) 0.088(2) -0.0052(15) -0.0182(17) -0.0060(15) C4 0.0354(15) 0.0516(19) 0.055(2) -0.0164(15) -0.0001(13) -0.0028(14) C5 0.0501(19) 0.055(2) 0.080(3) -0.0070(18) -0.0126(17) -0.0019(16) C41 0.0430(19) 0.088(3) 0.095(3) -0.015(2) -0.0134(18) 0.0048(19) C1 0.0387(18) 0.086(3) 0.101(3) -0.030(2) -0.0031(18) -0.015(2) C2 0.050(2) 0.058(2) 0.117(4) -0.029(2) 0.004(2) -0.0164(18) C3 0.0469(18) 0.050(2) 0.093(3) -0.0159(19) 0.0009(17) -0.0010(16) C6 0.0408(16) 0.0477(19) 0.055(2) -0.0099(15) -0.0014(13) -0.0031(14) C7 0.0409(17) 0.047(2) 0.096(3) -0.0111(19) -0.0078(17) -0.0080(16) C8 0.0454(17) 0.0476(19) 0.058(2) -0.0126(16) -0.0004(14) -0.0043(15) C9 0.0417(16) 0.0458(18) 0.053(2) -0.0119(15) -0.0021(13) -0.0041(14) C10 0.0431(16) 0.0440(18) 0.071(2) -0.0131(16) -0.0043(15) 0.0002(14) C11 0.0488(18) 0.0409(18) 0.070(2) -0.0163(16) -0.0045(15) -0.0006(14) C13 0.0431(17) 0.051(2) 0.088(3) -0.0294(18) -0.0051(16) -0.0013(15) C14 0.0488(18) 0.053(2) 0.090(3) -0.0385(19) -0.0015(17) -0.0068(16) C12 0.0451(16) 0.0398(17) 0.0458(19) -0.0095(14) -0.0028(13) -0.0083(13) C15 0.0472(16) 0.0376(17) 0.050(2) -0.0051(14) -0.0099(13) -0.0010(14) C16 0.0483(16) 0.0358(16) 0.0452(19) -0.0058(13) -0.0054(13) -0.0022(13) C18 0.0471(16) 0.0392(17) 0.058(2) -0.0086(14) -0.0108(14) 0.0012(13) C17 0.0474(16) 0.0312(15) 0.054(2) -0.0056(13) -0.0045(13) -0.0050(13) C20 0.0438(16) 0.0385(17) 0.059(2) -0.0069(14) -0.0098(14) -0.0069(13) C19 0.0535(18) 0.0295(16) 0.057(2) -0.0083(14) -0.0067(14) -0.0043(13) C21 0.0438(16) 0.0359(16) 0.0500(19) -0.0040(13) -0.0064(13) -0.0025(13) C22 0.0485(17) 0.0424(18) 0.056(2) 0.0004(15) -0.0077(14) -0.0035(14) C23 0.0448(16) 0.0383(17) 0.050(2) -0.0021(14) -0.0019(13) 0.0016(13) C24 0.0534(18) 0.0464(19) 0.070(2) -0.0127(16) -0.0163(16) -0.0018(15) C25 0.0556(19) 0.0418(18) 0.078(3) -0.0154(17) -0.0181(17) 0.0040(15) C26 0.0447(16) 0.0458(19) 0.049(2) -0.0069(14) 0.0007(13) -0.0022(14) C27 0.0426(16) 0.0453(19) 0.063(2) 0.0026(15) -0.0078(14) -0.0063(14) C28 0.0492(17) 0.0386(17) 0.059(2) -0.0066(15) -0.0059(14) -0.0066(14) C29 0.0411(17) 0.0475(19) 0.058(2) -0.0093(15) -0.0054(14) -0.0041(15) C30 0.0480(17) 0.0458(19) 0.048(2) -0.0036(14) -0.0043(13) -0.0025(14) C70 0.066(2) 0.048(2) 0.071(3) 0.0020(17) -0.0154(17) -0.0061(18) C31 0.0528(18) 0.0457(18) 0.047(2) -0.0084(14) -0.0042(14) -0.0008(14) C36 0.056(2) 0.047(2) 0.089(3) -0.0019(18) -0.0148(18) -0.0039(16) C35 0.054(2) 0.066(3) 0.121(4) -0.006(2) -0.029(2) -0.0023(19) C34 0.069(2) 0.069(3) 0.115(4) -0.009(2) -0.032(2) 0.013(2) C33 0.084(3) 0.051(2) 0.105(4) 0.006(2) -0.017(2) 0.011(2) C32 0.064(2) 0.051(2) 0.079(3) 0.0053(19) -0.0101(18) -0.0015(17) O5 0.0754(17) 0.0481(15) 0.120(3) -0.0029(15) -0.0153(16) -0.0125(13) N5 0.0594(17) 0.0473(18) 0.095(3) -0.0043(17) -0.0100(16) -0.0084(14) C43 0.131(4) 0.100(4) 0.134(5) 0.023(4) 0.004(4) -0.027(3) C40 0.098(3) 0.060(3) 0.124(4) -0.020(3) -0.021(3) -0.008(2) C42 0.051(2) 0.057(2) 0.115(4) -0.020(2) -0.013(2) -0.0029(18) O1 0.054(9) 0.039(5) 0.137(10) 0.016(5) -0.043(8) -0.003(5) O1' 0.067(12) 0.035(6) 0.178(13) -0.016(7) -0.034(9) 0.008(7) O6 0.0868(18) 0.0569(17) 0.119(3) -0.0244(16) -0.0278(17) 0.0195(15) N6 0.127(3) 0.051(2) 0.081(3) -0.0159(18) 0.016(2) 0.006(2) C39 0.101(3) 0.065(3) 0.085(3) -0.019(2) 0.001(2) 0.007(2) C38 0.170(5) 0.120(4) 0.140(5) -0.048(4) 0.042(4) -0.068(4) C37 0.234(6) 0.114(4) 0.113(5) -0.003(4) -0.009(4) 0.087(5) _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 O2 N10 1.215(3) . ? O3 C15 1.213(3) . ? O4 C22 1.217(4) . ? N1 C7 1.140(4) . ? N4 C70 1.143(4) . ? N2 C15 1.352(4) . ? N2 C12 1.407(4) . ? N2 H100 0.73(3) . ? N3 C22 1.354(4) . ? N3 C23 1.420(4) . ? N3 H101 0.94(4) . ? N10 O1 1.14(2) . ? N10 O1' 1.31(2) . ? N10 C19 1.468(4) . ? C4 C5 1.377(4) . ? C4 C3 1.384(4) . ? C4 C6 1.494(4) . ? C5 C41 1.378(5) . ? C5 H40 0.9300 . ? C41 C1 1.358(6) . ? C41 H41 0.9300 . ? C1 C2 1.363(5) . ? C1 H42 0.9300 . ? C2 C3 1.377(4) . ? C2 H43 0.9300 . ? C3 H44 0.9300 . ? C6 C8 1.333(4) . ? C6 C7 1.434(5) . ? C8 C9 1.468(4) . ? C8 H102 1.00(4) . ? C9 C14 1.386(4) . ? C9 C10 1.385(4) . ? C10 C11 1.378(4) . ? C10 H49 0.9300 . ? C11 C12 1.394(4) . ? C11 H50 0.9300 . ? C13 C12 1.369(4) . ? C13 C14 1.378(4) . ? C13 H51 0.9300 . ? C14 H52 0.9300 . ? C15 C16 1.508(4) . ? C16 C17 1.385(4) . ? C16 C18 1.390(4) . ? C18 C19 1.390(4) . ? C18 H56 0.9300 . ? C17 C21 1.396(4) . ? C17 H57 0.9300 . ? C20 C19 1.369(4) . ? C20 C21 1.382(4) . ? C20 H58 0.9300 . ? C21 C22 1.511(4) . ? C23 C24 1.381(4) . ? C23 C28 1.381(4) . ? C24 C25 1.372(4) . ? C24 H63 0.9300 . ? C25 C26 1.403(4) . ? C25 H64 0.9300 . ? C26 C27 1.384(4) . ? C26 C29 1.452(4) . ? C27 C28 1.379(4) . ? C27 H66 0.9300 . ? C28 H67 0.9300 . ? C29 C30 1.341(4) . ? C29 H103 0.86(3) . ? C30 C70 1.440(4) . ? C30 C31 1.496(4) . ? C31 C36 1.374(4) . ? C31 C32 1.375(4) . ? C36 C35 1.383(5) . ? C36 H72 0.9300 . ? C35 C34 1.371(6) . ? C35 H73 0.9300 . ? C34 C33 1.372(6) . ? C34 H74 0.9300 . ? C33 C32 1.387(5) . ? C33 H75 0.9300 . ? C32 H76 0.9300 . ? O5 C42 1.231(5) . ? N5 C42 1.315(5) . ? N5 C43 1.452(6) . ? N5 C40 1.456(6) . ? C43 H43A 0.9600 . ? C43 H43B 0.9600 . ? C43 H43C 0.9600 . ? C40 H40A 0.9600 . ? C40 H40B 0.9600 . ? C40 H40C 0.9600 . ? C42 H42A 0.9300 . ? O6 C39 1.194(5) . ? N6 C39 1.293(5) . ? N6 C37 1.409(6) . ? N6 C38 1.491(6) . ? C39 H39 0.9300 . ? C38 H38A 0.9600 . ? C38 H38B 0.9600 . ? C38 H38C 0.9600 . ? C37 H37A 0.9600 . ? C37 H37B 0.9600 . ? C37 H37C 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 C15 N2 C12 126.8(3) . . ? C15 N2 H100 118(3) . . ? C12 N2 H100 116(3) . . ? C22 N3 C23 125.0(3) . . ? C22 N3 H101 121(2) . . ? C23 N3 H101 114(2) . . ? O1 N10 O2 117.9(13) . . ? O1 N10 O1' 17(2) . . ? O2 N10 O1' 128.3(11) . . ? O1 N10 C19 123.7(13) . . ? O2 N10 C19 117.8(3) . . ? O1' N10 C19 113.4(11) . . ? C5 C4 C3 117.8(3) . . ? C5 C4 C6 121.9(3) . . ? C3 C4 C6 120.3(3) . . ? C4 C5 C41 120.7(3) . . ? C4 C5 H40 119.6 . . ? C41 C5 H40 119.6 . . ? C1 C41 C5 120.7(4) . . ? C1 C41 H41 119.6 . . ? C5 C41 H41 119.6 . . ? C41 C1 C2 119.5(3) . . ? C41 C1 H42 120.2 . . ? C2 C1 H42 120.2 . . ? C1 C2 C3 120.3(4) . . ? C1 C2 H43 119.9 . . ? C3 C2 H43 119.9 . . ? C2 C3 C4 120.9(3) . . ? C2 C3 H44 119.5 . . ? C4 C3 H44 119.5 . . ? C8 C6 C7 122.7(3) . . ? C8 C6 C4 123.1(3) . . ? C7 C6 C4 114.1(3) . . ? N1 C7 C6 175.8(4) . . ? C6 C8 C9 131.5(3) . . ? C6 C8 H102 114(2) . . ? C9 C8 H102 114(2) . . ? C14 C9 C10 116.5(3) . . ? C14 C9 C8 126.4(3) . . ? C10 C9 C8 117.0(3) . . ? C11 C10 C9 122.7(3) . . ? C11 C10 H49 118.6 . . ? C9 C10 H49 118.6 . . ? C10 C11 C12 119.5(3) . . ? C10 C11 H50 120.3 . . ? C12 C11 H50 120.3 . . ? C12 C13 C14 121.5(3) . . ? C12 C13 H51 119.2 . . ? C14 C13 H51 119.2 . . ? C13 C14 C9 121.3(3) . . ? C13 C14 H52 119.3 . . ? C9 C14 H52 119.3 . . ? C13 C12 C11 118.3(3) . . ? C13 C12 N2 118.9(3) . . ? C11 C12 N2 122.8(3) . . ? O3 C15 N2 122.9(3) . . ? O3 C15 C16 119.2(3) . . ? N2 C15 C16 117.8(3) . . ? C17 C16 C18 119.2(3) . . ? C17 C16 C15 125.1(3) . . ? C18 C16 C15 115.7(3) . . ? C19 C18 C16 118.5(3) . . ? C19 C18 H56 120.7 . . ? C16 C18 H56 120.7 . . ? C16 C17 C21 121.0(3) . . ? C16 C17 H57 119.5 . . ? C21 C17 H57 119.5 . . ? C19 C20 C21 118.4(3) . . ? C19 C20 H58 120.8 . . ? C21 C20 H58 120.8 . . ? C20 C19 C18 122.9(3) . . ? C20 C19 N10 119.5(3) . . ? C18 C19 N10 117.6(3) . . ? C20 C21 C17 119.9(3) . . ? C20 C21 C22 124.2(3) . . ? C17 C21 C22 115.9(3) . . ? O4 C22 N3 123.6(3) . . ? O4 C22 C21 118.9(3) . . ? N3 C22 C21 117.5(3) . . ? C24 C23 C28 119.0(3) . . ? C24 C23 N3 122.8(3) . . ? C28 C23 N3 118.1(3) . . ? C25 C24 C23 120.3(3) . . ? C25 C24 H63 119.8 . . ? C23 C24 H63 119.8 . . ? C24 C25 C26 122.1(3) . . ? C24 C25 H64 119.0 . . ? C26 C25 H64 119.0 . . ? C27 C26 C25 115.9(3) . . ? C27 C26 C29 119.1(3) . . ? C25 C26 C29 124.9(3) . . ? C28 C27 C26 122.6(3) . . ? C28 C27 H66 118.7 . . ? C26 C27 H66 118.7 . . ? C27 C28 C23 119.9(3) . . ? C27 C28 H67 120.0 . . ? C23 C28 H67 120.0 . . ? C30 C29 C26 131.4(3) . . ? C30 C29 H103 116(2) . . ? C26 C29 H103 112(2) . . ? C29 C30 C70 121.1(3) . . ? C29 C30 C31 124.7(3) . . ? C70 C30 C31 114.3(3) . . ? N4 C70 C30 176.2(4) . . ? C36 C31 C32 118.6(3) . . ? C36 C31 C30 121.0(3) . . ? C32 C31 C30 120.3(3) . . ? C31 C36 C35 120.9(3) . . ? C31 C36 H72 119.5 . . ? C35 C36 H72 119.5 . . ? C34 C35 C36 120.2(4) . . ? C34 C35 H73 119.9 . . ? C36 C35 H73 119.9 . . ? C33 C34 C35 119.4(4) . . ? C33 C34 H74 120.3 . . ? C35 C34 H74 120.3 . . ? C34 C33 C32 120.2(4) . . ? C34 C33 H75 119.9 . . ? C32 C33 H75 119.9 . . ? C31 C32 C33 120.7(3) . . ? C31 C32 H76 119.7 . . ? C33 C32 H76 119.6 . . ? C42 N5 C43 121.6(4) . . ? C42 N5 C40 120.8(4) . . ? C43 N5 C40 117.4(4) . . ? N5 C43 H43A 109.5 . . ? N5 C43 H43B 109.5 . . ? H43A C43 H43B 109.5 . . ? N5 C43 H43C 109.5 . . ? H43A C43 H43C 109.5 . . ? H43B C43 H43C 109.5 . . ? N5 C40 H40A 109.5 . . ? N5 C40 H40B 109.5 . . ? H40A C40 H40B 109.5 . . ? N5 C40 H40C 109.5 . . ? H40A C40 H40C 109.5 . . ? H40B C40 H40C 109.5 . . ? O5 C42 N5 125.3(4) . . ? O5 C42 H42A 117.4 . . ? N5 C42 H42A 117.4 . . ? C39 N6 C37 126.6(5) . . ? C39 N6 C38 116.9(5) . . ? C37 N6 C38 116.4(5) . . ? O6 C39 N6 129.3(5) . . ? O6 C39 H39 115.3 . . ? N6 C39 H39 115.3 . . ? N6 C38 H38A 109.5 . . ? N6 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? N6 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? N6 C37 H37A 109.5 . . ? N6 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? N6 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? 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 N3 H101 O5 0.94(4) 1.99(4) 2.922(4) 169(3) 2_656 _diffrn_measured_fraction_theta_max 0.968 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.968 _refine_diff_density_max 0.402 _refine_diff_density_min -0.242 _refine_diff_density_rms 0.053