# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2003 data_global _journal_coden_Cambridge 440 _journal_volume ? _journal_year ? _journal_page_first ? _publ_requested_journal 'New Journal of Chemistry' loop_ _publ_author_name 'Vieri Fusi' 'Mauro Formica' 'Luca Giorgi' 'Annalisa Guerri' 'Simone Lucarini' 'Mauro Micheloni' 'Paola Paoli' 'Roberto Pontellini' 'Patrizia Rossi' 'Giorgio Tarzia' 'Giovanni Zappia' _publ_contact_author 'Fusi Vieri' _publ_contact_author_address ; Institute of Chemical Science University of Urbino P.zza Rinascimento, 6 60129 Urbino, ITALY ; _publ_contact_author_email vieri@chim.uniurb.it _publ_section_title ; New Ligand Bearing Preorganized Binding Side-Arms Interacting with Ammonium Cations: Synthesis, Conformational Studies and Crystal Structure. ; data_L _database_code_CSD 213787 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; (C24 H35 N6 O6 1+),(H2 O)8,(Cl 1-) ; _chemical_formula_sum 'C24 H51 Cl N6 O14' _chemical_formula_weight 682.15 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 '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 9.506(4) _cell_length_b 9.904(3) _cell_length_c 20.616(6) _cell_angle_alpha 95.45(4) _cell_angle_beta 98.14(4) _cell_angle_gamma 118.46(3) _cell_volume 1659.5(10) _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 prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.6 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.365 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 730 _exptl_absorpt_coefficient_mu 1.654 _exptl_absorpt_correction_type 'REFDELF (WALKER and STUART, 1983)' _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54180 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Siemens P4' _diffrn_measurement_method \q/2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% ? _diffrn_reflns_number 5850 _diffrn_reflns_av_R_equivalents 0.0502 _diffrn_reflns_av_sigmaI/netI 0.0429 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 1 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.20 _diffrn_reflns_theta_max 60.00 _reflns_number_total 4826 _reflns_number_gt 4082 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens P4' _computing_cell_refinement 'Siemens P4' _computing_data_reduction 'Siemens P4' _computing_structure_solution 'SIR97 (Altomare,1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP (Farruggia, 1997)' _computing_publication_material 'PARST97 (Nardelli, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1365P)^2^+0.8532P] 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 0.0042(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4826 _refine_ls_number_parameters 416 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0782 _refine_ls_R_factor_gt 0.0691 _refine_ls_wR_factor_ref 0.2090 _refine_ls_wR_factor_gt 0.1972 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _refine_ls_shift/su_max 0.133 _refine_ls_shift/su_mean 0.009 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 Cl1 Cl 0.69026(12) 0.38025(12) 0.49945(5) 0.0696(3) Uani 1 1 d . . . O1 O 0.4394(4) 0.3931(3) 0.87300(17) 0.0967(11) Uani 1 1 d . . . C1 C 0.5022(4) 0.5399(4) 0.88433(17) 0.0592(9) Uani 1 1 d . . . C2 C 0.4646(6) 0.6222(9) 0.9320(2) 0.0917(16) Uani 1 1 d . . . O2 O 0.3553(5) 0.5365(8) 0.96715(19) 0.159(2) Uani 1 1 d . . . H2 H 0.3048 0.4447 0.9483 0.238 Uiso 1 1 calc R . . C3 C 0.5342(10) 0.7793(11) 0.9406(3) 0.122(3) Uani 1 1 d . . . H3 H 0.5079 0.8321 0.9721 0.146 Uiso 1 1 calc R . . C4 C 0.6435(7) 0.8616(6) 0.9030(3) 0.101(2) Uani 1 1 d . . . H4 H 0.6910 0.9698 0.9093 0.121 Uiso 1 1 calc R . . C5 C 0.6828(5) 0.7857(4) 0.8567(2) 0.0635(10) Uani 1 1 d . . . H5 H 0.7563 0.8405 0.8308 0.076 Uiso 1 1 calc R . . N1 N 0.6116(3) 0.6268(3) 0.84912(12) 0.0467(6) Uani 1 1 d . . . C6 C 0.6504(4) 0.5451(4) 0.79823(16) 0.0544(8) Uani 1 1 d . . . H6A H 0.6640 0.4633 0.8153 0.065 Uiso 1 1 calc R . . H6B H 0.7526 0.6178 0.7872 0.065 Uiso 1 1 calc R . . C7 C 0.5139(4) 0.4738(3) 0.73569(15) 0.0432(7) Uani 1 1 d . . . O3 O 0.3953(3) 0.4933(2) 0.73305(11) 0.0525(6) Uani 1 1 d . . . N2 N 0.5323(3) 0.3935(3) 0.68415(12) 0.0417(6) Uani 1 1 d . . . C8 C 0.6741(4) 0.3707(3) 0.68676(17) 0.0478(8) Uani 1 1 d . . . H8A H 0.7712 0.4658 0.7110 0.057 Uiso 1 1 calc R . . H8B H 0.6884 0.3531 0.6416 0.057 Uiso 1 1 calc R . . C9 C 0.6608(4) 0.2351(3) 0.71947(16) 0.0459(7) Uani 1 1 d . . . H9A H 0.7693 0.2481 0.7321 0.055 Uiso 1 1 calc R . . H9B H 0.6208 0.2392 0.7600 0.055 Uiso 1 1 calc R . . N3 N 0.5510(3) 0.0783(3) 0.67666(12) 0.0399(6) Uani 1 1 d . . . HN3 H 0.419(8) 0.063(7) 0.658(3) 0.16(2) Uiso 1 1 d . . . C10 C 0.6293(4) 0.0539(4) 0.62226(17) 0.0529(8) Uani 1 1 d . . . H10A H 0.5575 -0.0474 0.5948 0.079 Uiso 1 1 calc R . . H10B H 0.7309 0.0603 0.6414 0.079 Uiso 1 1 calc R . . H10C H 0.6498 0.1329 0.5955 0.079 Uiso 1 1 calc R . . C11 C 0.5221(4) -0.0415(3) 0.71969(16) 0.0455(7) Uani 1 1 d . . . H11A H 0.4969 -0.0091 0.7603 0.055 Uiso 1 1 calc R . . H11B H 0.6226 -0.0449 0.7322 0.055 Uiso 1 1 calc R . . C12 C 0.3849(4) -0.2054(3) 0.68729(16) 0.0472(7) Uani 1 1 d . . . H12A H 0.3955 -0.2279 0.6420 0.057 Uiso 1 1 calc R . . H12B H 0.3978 -0.2796 0.7114 0.057 Uiso 1 1 calc R . . N4 N 0.2200(3) -0.2291(3) 0.68547(12) 0.0419(6) Uani 1 1 d . . . C13 C 0.1221(4) -0.2332(3) 0.62259(14) 0.0478(8) Uani 1 1 d . . . H13A H 0.0119 -0.3208 0.6162 0.057 Uiso 1 1 calc R . . H13B H 0.1688 -0.2511 0.5861 0.057 Uiso 1 1 calc R . . C14 C 0.1125(4) -0.0849(3) 0.61945(15) 0.0460(7) Uani 1 1 d . . . H14A H 0.0192 -0.1086 0.5849 0.055 Uiso 1 1 calc R . . H14B H 0.0934 -0.0518 0.6616 0.055 Uiso 1 1 calc R . . N5 N 0.2618(3) 0.0471(3) 0.60577(11) 0.0399(6) Uani 1 1 d . . . C15 C 0.2747(5) 0.0149(4) 0.53556(15) 0.0550(8) Uani 1 1 d . . . H15A H 0.2811 -0.0790 0.5280 0.082 Uiso 1 1 calc R . . H15B H 0.3714 0.1008 0.5275 0.082 Uiso 1 1 calc R . . H15C H 0.1800 0.0020 0.5059 0.082 Uiso 1 1 calc R . . C16 C 0.2516(4) 0.1925(3) 0.61886(16) 0.0461(7) Uani 1 1 d . . . H16A H 0.2186 0.1980 0.6610 0.055 Uiso 1 1 calc R . . H16B H 0.1673 0.1863 0.5842 0.055 Uiso 1 1 calc R . . C17 C 0.4109(4) 0.3415(3) 0.62141(15) 0.0469(7) Uani 1 1 d . . . H17A H 0.4589 0.3252 0.5850 0.056 Uiso 1 1 calc R . . H17B H 0.3865 0.4242 0.6143 0.056 Uiso 1 1 calc R . . O4 O 0.0081(3) -0.2823(3) 0.73598(11) 0.0509(6) Uani 1 1 d . . . C18 C 0.1462(4) -0.2629(3) 0.73747(14) 0.0403(7) Uani 1 1 d . . . C19 C 0.2397(4) -0.2802(4) 0.79985(15) 0.0470(7) Uani 1 1 d . . . H19A H 0.2658 -0.3617 0.7884 0.056 Uiso 1 1 calc R . . H19B H 0.3416 -0.1830 0.8173 0.056 Uiso 1 1 calc R . . N6 N 0.1417(3) -0.3195(3) 0.85063(12) 0.0447(6) Uani 1 1 d . . . C20 C 0.0466(4) -0.4741(4) 0.85483(16) 0.0509(8) Uani 1 1 d . . . H20 H 0.0491 -0.5513 0.8263 0.061 Uiso 1 1 calc R . . C21 C -0.0489(4) -0.5147(4) 0.89924(17) 0.0579(9) Uani 1 1 d . . . H21 H -0.1120 -0.6193 0.9020 0.070 Uiso 1 1 calc R . . C22 C -0.0532(4) -0.3973(4) 0.94204(17) 0.0593(9) Uani 1 1 d . . . H22 H -0.1196 -0.4243 0.9731 0.071 Uiso 1 1 calc R . . C23 C 0.0396(4) -0.2450(4) 0.93785(16) 0.0553(8) Uani 1 1 d . . . O5 O 0.0459(4) -0.1227(3) 0.97648(15) 0.0793(8) Uani 1 1 d . . . HO5 H -0.012(6) -0.159(6) 1.014(3) 0.102(16) Uiso 1 1 d . . . C24 C 0.1415(4) -0.1997(4) 0.89030(16) 0.0500(8) Uani 1 1 d . . . O6 O 0.2272(3) -0.0609(3) 0.88360(13) 0.0670(7) Uani 1 1 d . . . O7 O 0.1355(4) 0.1808(4) 0.92782(15) 0.0815(8) Uani 1 1 d . . . O8 O -0.0410(6) 0.1268(5) 0.7919(3) 0.1415(18) Uani 1 1 d . . . O9 O 0.0576(4) 0.3605(4) 0.69870(19) 0.1011(11) Uani 1 1 d . . . O10 O 0.2815(5) 0.1172(4) 0.77648(17) 0.1109(13) Uani 1 1 d . . . O11 O 0.5662(5) 0.1880(5) 0.9080(2) 0.1197(13) Uani 1 1 d . . . O12 O 1.0106(4) 0.3632(4) 0.56000(19) 0.0947(10) Uani 1 1 d . . . O13 O 0.3256(4) 0.3102(4) 0.44063(18) 0.0937(10) Uani 1 1 d . . . O14 O 0.2154(5) 0.1853(5) 0.30247(19) 0.1040(11) 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 Cl1 0.0647(6) 0.0840(7) 0.0666(6) 0.0118(5) 0.0206(4) 0.0406(5) O1 0.087(2) 0.0635(19) 0.097(2) 0.0368(16) 0.0043(17) 0.0047(16) C1 0.0515(19) 0.062(2) 0.0516(19) 0.0136(16) 0.0047(15) 0.0194(17) C2 0.071(3) 0.169(6) 0.050(2) 0.014(3) 0.012(2) 0.074(3) O2 0.101(3) 0.329(8) 0.084(3) 0.086(4) 0.052(2) 0.119(4) C3 0.140(6) 0.206(8) 0.058(3) -0.040(4) -0.017(3) 0.137(6) C4 0.109(4) 0.072(3) 0.103(4) -0.047(3) -0.043(3) 0.059(3) C5 0.057(2) 0.0394(18) 0.074(2) -0.0005(16) -0.0056(17) 0.0156(16) N1 0.0467(14) 0.0373(13) 0.0461(14) -0.0014(11) 0.0025(11) 0.0165(11) C6 0.056(2) 0.0549(19) 0.0501(18) -0.0010(15) 0.0032(15) 0.0300(16) C7 0.0477(18) 0.0308(14) 0.0460(16) 0.0079(12) 0.0064(13) 0.0164(13) O3 0.0542(14) 0.0461(12) 0.0579(13) 0.0001(10) 0.0016(10) 0.0298(11) N2 0.0473(14) 0.0297(12) 0.0432(13) 0.0066(10) 0.0096(11) 0.0155(11) C8 0.0447(17) 0.0324(15) 0.0590(19) 0.0063(13) 0.0193(14) 0.0117(13) C9 0.0388(16) 0.0412(16) 0.0530(17) 0.0042(13) 0.0077(13) 0.0176(13) N3 0.0411(13) 0.0309(12) 0.0468(14) 0.0082(10) 0.0150(11) 0.0154(10) C10 0.060(2) 0.0422(16) 0.0599(19) 0.0110(14) 0.0304(16) 0.0227(15) C11 0.0416(16) 0.0432(16) 0.0544(18) 0.0177(13) 0.0159(13) 0.0204(14) C12 0.0567(19) 0.0346(15) 0.0554(18) 0.0156(13) 0.0238(15) 0.0224(14) N4 0.0462(14) 0.0303(12) 0.0423(13) 0.0094(10) 0.0113(11) 0.0126(10) C13 0.0534(18) 0.0328(15) 0.0389(15) 0.0055(12) 0.0045(13) 0.0087(13) C14 0.0435(17) 0.0356(15) 0.0466(16) 0.0110(12) 0.0079(13) 0.0101(13) N5 0.0468(14) 0.0294(12) 0.0381(12) 0.0074(9) 0.0117(10) 0.0137(11) C15 0.074(2) 0.0411(17) 0.0411(17) 0.0073(13) 0.0146(15) 0.0212(16) C16 0.0507(18) 0.0338(15) 0.0482(17) 0.0062(12) 0.0044(13) 0.0186(14) C17 0.0595(19) 0.0300(14) 0.0425(16) 0.0088(12) 0.0080(14) 0.0159(14) O4 0.0372(12) 0.0531(13) 0.0552(13) 0.0193(10) 0.0110(9) 0.0149(10) C18 0.0401(17) 0.0289(14) 0.0421(16) 0.0081(11) 0.0081(12) 0.0095(12) C19 0.0453(17) 0.0495(17) 0.0450(16) 0.0143(13) 0.0136(13) 0.0207(14) N6 0.0443(14) 0.0431(14) 0.0419(13) 0.0134(11) 0.0101(11) 0.0166(11) C20 0.0541(19) 0.0404(16) 0.0522(18) 0.0146(14) 0.0104(15) 0.0182(15) C21 0.057(2) 0.0498(19) 0.059(2) 0.0233(16) 0.0132(16) 0.0180(16) C22 0.0524(19) 0.074(2) 0.0477(18) 0.0258(17) 0.0167(15) 0.0248(18) C23 0.0538(19) 0.062(2) 0.0445(17) 0.0078(15) 0.0094(14) 0.0255(17) O5 0.088(2) 0.0752(18) 0.0680(17) -0.0006(14) 0.0287(15) 0.0348(16) C24 0.0464(18) 0.0461(18) 0.0481(17) 0.0096(14) 0.0071(14) 0.0163(15) O6 0.0724(16) 0.0424(13) 0.0731(16) 0.0107(11) 0.0230(13) 0.0163(12) O7 0.085(2) 0.085(2) 0.0831(19) 0.0221(15) 0.0382(16) 0.0422(16) O8 0.122(3) 0.105(3) 0.159(4) 0.028(3) -0.027(3) 0.041(3) O9 0.075(2) 0.093(2) 0.112(3) -0.0061(19) 0.0358(18) 0.0243(17) O10 0.146(3) 0.076(2) 0.083(2) 0.0183(17) 0.025(2) 0.033(2) O11 0.099(3) 0.112(3) 0.136(3) 0.028(2) 0.027(2) 0.041(2) O12 0.081(2) 0.078(2) 0.118(3) 0.0305(18) 0.0071(18) 0.0359(17) O13 0.079(2) 0.0736(19) 0.112(3) 0.0127(17) -0.0003(17) 0.0313(16) O14 0.127(3) 0.122(3) 0.107(3) 0.042(2) 0.053(2) 0.085(3) _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 O1 C1 1.262(5) . ? C1 N1 1.352(5) . ? C1 C2 1.408(7) . ? C2 O2 1.348(7) . ? C2 C3 1.350(9) . ? O2 H2 0.8200 . ? C3 C4 1.372(10) . ? C3 H3 0.9300 . ? C4 C5 1.360(7) . ? C4 H4 0.9300 . ? C5 N1 1.367(4) . ? C5 H5 0.9300 . ? N1 C6 1.457(4) . ? C6 C7 1.525(4) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 O3 1.226(4) . ? C7 N2 1.348(4) . ? N2 C8 1.464(4) . ? N2 C17 1.468(4) . ? C8 C9 1.519(4) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 N3 1.488(4) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? N3 C10 1.492(4) . ? N3 C11 1.494(4) . ? N3 HN3 1.19(7) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C12 1.520(4) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 N4 1.464(4) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? N4 C18 1.345(4) . ? N4 C13 1.470(4) . ? C13 C14 1.521(4) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 N5 1.489(4) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? N5 C15 1.487(4) . ? N5 C16 1.491(4) . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 C17 1.519(4) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? O4 C18 1.228(4) . ? C18 C19 1.528(4) . ? C19 N6 1.457(4) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? N6 C24 1.376(4) . ? N6 C20 1.378(4) . ? C20 C21 1.335(5) . ? C20 H20 0.9300 . ? C21 C22 1.412(5) . ? C21 H21 0.9300 . ? C22 C23 1.356(5) . ? C22 H22 0.9300 . ? C23 O5 1.356(5) . ? C23 C24 1.427(5) . ? O5 HO5 1.01(6) . ? C24 O6 1.254(4) . ? 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 O1 C1 N1 119.7(4) . . ? O1 C1 C2 124.0(4) . . ? N1 C1 C2 116.4(4) . . ? O2 C2 C3 122.5(6) . . ? O2 C2 C1 116.8(6) . . ? C3 C2 C1 120.8(5) . . ? C2 O2 H2 109.5 . . ? C2 C3 C4 120.4(4) . . ? C2 C3 H3 119.8 . . ? C4 C3 H3 119.8 . . ? C5 C4 C3 120.3(5) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.8 . . ? C4 C5 N1 118.3(5) . . ? C4 C5 H5 120.9 . . ? N1 C5 H5 120.9 . . ? C1 N1 C5 123.9(3) . . ? C1 N1 C6 117.9(3) . . ? C5 N1 C6 118.2(3) . . ? N1 C6 C7 110.4(3) . . ? N1 C6 H6A 109.6 . . ? C7 C6 H6A 109.6 . . ? N1 C6 H6B 109.6 . . ? C7 C6 H6B 109.6 . . ? H6A C6 H6B 108.1 . . ? O3 C7 N2 122.6(3) . . ? O3 C7 C6 120.2(3) . . ? N2 C7 C6 117.2(3) . . ? C7 N2 C8 122.9(3) . . ? C7 N2 C17 116.9(3) . . ? C8 N2 C17 119.9(2) . . ? N2 C8 C9 114.2(2) . . ? N2 C8 H8A 108.7 . . ? C9 C8 H8A 108.7 . . ? N2 C8 H8B 108.7 . . ? C9 C8 H8B 108.7 . . ? H8A C8 H8B 107.6 . . ? N3 C9 C8 114.3(3) . . ? N3 C9 H9A 108.7 . . ? C8 C9 H9A 108.7 . . ? N3 C9 H9B 108.7 . . ? C8 C9 H9B 108.7 . . ? H9A C9 H9B 107.6 . . ? C9 N3 C10 110.1(2) . . ? C9 N3 C11 107.9(2) . . ? C10 N3 C11 110.1(2) . . ? C9 N3 HN3 110(3) . . ? C10 N3 HN3 114(3) . . ? C11 N3 HN3 104(3) . . ? N3 C10 H10A 109.5 . . ? N3 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? N3 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N3 C11 C12 114.5(3) . . ? N3 C11 H11A 108.6 . . ? C12 C11 H11A 108.6 . . ? N3 C11 H11B 108.6 . . ? C12 C11 H11B 108.6 . . ? H11A C11 H11B 107.6 . . ? N4 C12 C11 114.4(2) . . ? N4 C12 H12A 108.7 . . ? C11 C12 H12A 108.7 . . ? N4 C12 H12B 108.7 . . ? C11 C12 H12B 108.7 . . ? H12A C12 H12B 107.6 . . ? C18 N4 C12 122.7(2) . . ? C18 N4 C13 117.4(3) . . ? C12 N4 C13 119.5(2) . . ? N4 C13 C14 114.2(2) . . ? N4 C13 H13A 108.7 . . ? C14 C13 H13A 108.7 . . ? N4 C13 H13B 108.7 . . ? C14 C13 H13B 108.7 . . ? H13A C13 H13B 107.6 . . ? N5 C14 C13 114.2(3) . . ? N5 C14 H14A 108.7 . . ? C13 C14 H14A 108.7 . . ? N5 C14 H14B 108.7 . . ? C13 C14 H14B 108.7 . . ? H14A C14 H14B 107.6 . . ? C15 N5 C14 110.4(2) . . ? C15 N5 C16 110.6(2) . . ? C14 N5 C16 108.4(2) . . ? N5 C15 H15A 109.5 . . ? N5 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? N5 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? N5 C16 C17 114.0(3) . . ? N5 C16 H16A 108.8 . . ? C17 C16 H16A 108.8 . . ? N5 C16 H16B 108.8 . . ? C17 C16 H16B 108.8 . . ? H16A C16 H16B 107.7 . . ? N2 C17 C16 114.4(2) . . ? N2 C17 H17A 108.7 . . ? C16 C17 H17A 108.7 . . ? N2 C17 H17B 108.6 . . ? C16 C17 H17B 108.6 . . ? H17A C17 H17B 107.6 . . ? O4 C18 N4 122.7(3) . . ? O4 C18 C19 119.8(3) . . ? N4 C18 C19 117.5(3) . . ? N6 C19 C18 110.4(2) . . ? N6 C19 H19A 109.6 . . ? C18 C19 H19A 109.6 . . ? N6 C19 H19B 109.6 . . ? C18 C19 H19B 109.6 . . ? H19A C19 H19B 108.1 . . ? C24 N6 C20 122.6(3) . . ? C24 N6 C19 118.1(3) . . ? C20 N6 C19 119.3(3) . . ? C21 C20 N6 120.9(3) . . ? C21 C20 H20 119.6 . . ? N6 C20 H20 119.6 . . ? C20 C21 C22 119.4(3) . . ? C20 C21 H21 120.3 . . ? C22 C21 H21 120.3 . . ? C23 C22 C21 119.9(3) . . ? C23 C22 H22 120.1 . . ? C21 C22 H22 120.1 . . ? C22 C23 O5 125.0(3) . . ? C22 C23 C24 121.4(3) . . ? O5 C23 C24 113.6(3) . . ? C23 O5 HO5 110(3) . . ? O6 C24 N6 120.3(3) . . ? O6 C24 C23 123.9(3) . . ? N6 C24 C23 115.8(3) . . ? _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 60.00 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 0.493 _refine_diff_density_min -0.347 _refine_diff_density_rms 0.070