# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Dr Gary Weisman' _publ_contact_author_email gary.weisman@unh.edu _publ_section_title ; Synthesis, Cu(II) complexation, 64Cu-labeling and biological evaluation of cross-bridged cyclam chelators with phosphonate pendant arms ; _publ_author_name G.Weisman # Attachment '- CIF_Cu-CB-TE1A1P.txt' data_wong190 _database_code_depnum_ccdc_archive 'CCDC 843734' #TrackingRef '- CIF_Cu-CB-TE1A1P.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H80 Cu2 N8 O21 P2' _chemical_formula_weight 1078.04 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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pccn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z' '-x, y+1/2, -z+1/2' 'x+1/2, -y, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z' 'x, -y-1/2, z-1/2' '-x-1/2, y, z-1/2' _cell_length_a 10.1989(19) _cell_length_b 35.067(7) _cell_length_c 12.943(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4629.2(15) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9839 _cell_measurement_theta_min 2.61 _cell_measurement_theta_max 27.86 _exptl_crystal_description PLATE _exptl_crystal_colour blue _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.547 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2288 _exptl_absorpt_coefficient_mu 1.073 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8141 _exptl_absorpt_correction_T_max 0.9003 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 57822 _diffrn_reflns_av_R_equivalents 0.0564 _diffrn_reflns_av_sigmaI/netI 0.0311 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -46 _diffrn_reflns_limit_k_max 45 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 28.29 _reflns_number_total 5510 _reflns_number_gt 4831 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0460P)^2^+17.6017P] 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 5510 _refine_ls_number_parameters 322 _refine_ls_number_restraints 17 _refine_ls_R_factor_all 0.0568 _refine_ls_R_factor_gt 0.0484 _refine_ls_wR_factor_ref 0.1392 _refine_ls_wR_factor_gt 0.1350 _refine_ls_goodness_of_fit_ref 1.157 _refine_ls_restrained_S_all 1.156 _refine_ls_shift/su_max 0.039 _refine_ls_shift/su_mean 0.001 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 Cu1 Cu 0.48061(4) 0.607123(11) 0.22361(3) 0.01115(12) Uani 1 1 d . . . P1 P 0.49840(8) 0.55195(2) 0.42899(7) 0.01387(18) Uani 1 1 d . . . O1 O 0.5225(2) 0.59390(7) 0.41400(19) 0.0172(5) Uani 1 1 d . . . O2 O 0.6357(2) 0.53183(7) 0.4473(2) 0.0175(5) Uani 1 1 d D . . O3 O 0.4026(2) 0.53990(7) 0.51221(19) 0.0175(5) Uani 1 1 d . . . O4 O 0.2882(2) 0.60715(6) 0.25069(18) 0.0148(5) Uani 1 1 d . . . O5 O 0.1242(2) 0.64695(7) 0.2862(2) 0.0201(5) Uani 1 1 d . . . N1 N 0.4863(3) 0.54876(8) 0.2118(2) 0.0136(5) Uani 1 1 d . . . N2 N 0.4550(3) 0.62148(8) 0.0578(2) 0.0148(5) Uani 1 1 d . . . N3 N 0.4620(3) 0.66560(8) 0.2450(2) 0.0144(5) Uani 1 1 d . . . N4 N 0.6762(3) 0.60582(8) 0.1937(2) 0.0141(5) Uani 1 1 d . . . C1 C 0.7207(3) 0.56761(10) 0.2318(3) 0.0178(7) Uani 1 1 d . . . H1B H 0.7254 0.5679 0.3082 0.021 Uiso 1 1 calc R . . H1C H 0.8096 0.5621 0.2048 0.021 Uiso 1 1 calc R . . C2 C 0.6263(3) 0.53653(9) 0.1968(3) 0.0165(7) Uani 1 1 d . . . H2B H 0.6417 0.5308 0.1229 0.020 Uiso 1 1 calc R . . H2C H 0.6430 0.5130 0.2369 0.020 Uiso 1 1 calc R . . C3 C 0.4027(3) 0.53425(9) 0.1238(3) 0.0175(7) Uani 1 1 d . . . H3B H 0.3097 0.5394 0.1407 0.021 Uiso 1 1 calc R . . H3C H 0.4135 0.5062 0.1197 0.021 Uiso 1 1 calc R . . C4 C 0.4312(3) 0.55092(10) 0.0180(3) 0.0181(7) Uani 1 1 d . . . H4A H 0.3905 0.5342 -0.0347 0.022 Uiso 1 1 calc R . . H4B H 0.5271 0.5503 0.0067 0.022 Uiso 1 1 calc R . . C5 C 0.3834(3) 0.59158(10) -0.0002(3) 0.0176(7) Uani 1 1 d . . . H5A H 0.3904 0.5973 -0.0749 0.021 Uiso 1 1 calc R . . H5B H 0.2895 0.5930 0.0187 0.021 Uiso 1 1 calc R . . C6 C 0.3773(3) 0.65691(9) 0.0623(3) 0.0161(6) Uani 1 1 d . . . H6A H 0.2852 0.6507 0.0797 0.019 Uiso 1 1 calc R . . H6B H 0.3782 0.6694 -0.0062 0.019 Uiso 1 1 calc R . . C7 C 0.4327(4) 0.68417(9) 0.1432(3) 0.0170(6) Uani 1 1 d . . . H7A H 0.5144 0.6956 0.1159 0.020 Uiso 1 1 calc R . . H7B H 0.3691 0.7051 0.1545 0.020 Uiso 1 1 calc R . . C8 C 0.5771(4) 0.68455(10) 0.2940(3) 0.0195(7) Uani 1 1 d . . . H8A H 0.5832 0.6761 0.3669 0.023 Uiso 1 1 calc R . . H8B H 0.5624 0.7125 0.2941 0.023 Uiso 1 1 calc R . . C9 C 0.7066(4) 0.67622(10) 0.2405(3) 0.0217(7) Uani 1 1 d . . . H9A H 0.7747 0.6934 0.2691 0.026 Uiso 1 1 calc R . . H9B H 0.6975 0.6820 0.1660 0.026 Uiso 1 1 calc R . . C10 C 0.7521(3) 0.63512(10) 0.2525(3) 0.0206(7) Uani 1 1 d . . . H10A H 0.8450 0.6336 0.2307 0.025 Uiso 1 1 calc R . . H10B H 0.7486 0.6284 0.3268 0.025 Uiso 1 1 calc R . . C11 C 0.6983(3) 0.60825(10) 0.0789(3) 0.0191(7) Uani 1 1 d . . . H11A H 0.7078 0.5821 0.0513 0.023 Uiso 1 1 calc R . . H11B H 0.7819 0.6218 0.0663 0.023 Uiso 1 1 calc R . . C12 C 0.5887(3) 0.62865(10) 0.0180(3) 0.0193(7) Uani 1 1 d . . . H12A H 0.6056 0.6564 0.0196 0.023 Uiso 1 1 calc R . . H12B H 0.5927 0.6203 -0.0550 0.023 Uiso 1 1 calc R . . C13 C 0.2430(3) 0.63939(9) 0.2807(2) 0.0146(6) Uani 1 1 d . . . C14 C 0.3454(3) 0.66847(9) 0.3134(3) 0.0169(7) Uani 1 1 d . . . H14A H 0.3080 0.6945 0.3090 0.020 Uiso 1 1 calc R . . H14B H 0.3717 0.6637 0.3859 0.020 Uiso 1 1 calc R . . C15 C 0.4309(3) 0.53276(9) 0.3095(2) 0.0134(6) Uani 1 1 d . . . H15A H 0.4450 0.5048 0.3092 0.016 Uiso 1 1 calc R . . H15B H 0.3351 0.5372 0.3095 0.016 Uiso 1 1 calc R . . O6 O 0.4607(4) 0.72076(9) -0.1985(4) 0.0660(14) Uani 1 1 d D . . H6C H 0.533(4) 0.7206(19) -0.171(6) 0.099 Uiso 1 1 d D . . H6D H 0.434(6) 0.6989(8) -0.196(6) 0.099 Uiso 1 1 d D . . O10 O 0.0582(3) 0.55853(9) 0.2193(2) 0.0332(7) Uani 1 1 d D . . H10D H 0.066(5) 0.5539(15) 0.1573(13) 0.050 Uiso 1 1 d D . . H10C H 0.120(4) 0.5727(13) 0.232(4) 0.050 Uiso 1 1 d D . . O11 O 0.4697(3) 0.64332(7) 0.5692(2) 0.0241(6) Uani 1 1 d D . . H11D H 0.472(5) 0.6258(8) 0.528(2) 0.036 Uiso 1 1 d D . . H11C H 0.462(5) 0.6334(10) 0.6260(14) 0.036 Uiso 1 1 d D . . H2P H 0.626(5) 0.5127(7) 0.459(4) 0.032(14) Uiso 1 1 d D . . O9 O 0.6294(3) 0.73334(8) -0.0351(3) 0.0287(6) Uani 1 1 d . . . H9D H 0.587(5) 0.7526(16) 0.014(4) 0.043 Uiso 1 1 d . . . H9C H 0.594(6) 0.7276(16) -0.080(4) 0.043 Uiso 1 1 d . . . O7 O 0.4656(4) 0.77950(10) 0.0853(4) 0.0654(15) Uani 1 1 d D . . H7D H 0.465(7) 0.8025(4) 0.093(6) 0.098 Uiso 1 1 d D . . H7C H 0.397(5) 0.7741(18) 0.056(6) 0.098 Uiso 1 1 d D . . O8 O 0.2500 0.7500 -0.0179(4) 0.0593(17) Uani 1 2 d SD . . H8C H 0.314(5) 0.744(2) -0.052(5) 0.089 Uiso 1 1 d 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 Cu1 0.01241(19) 0.00950(19) 0.0115(2) -0.00042(14) 0.00054(14) 0.00010(13) P1 0.0180(4) 0.0101(4) 0.0135(4) 0.0010(3) 0.0005(3) 0.0013(3) O1 0.0232(12) 0.0107(11) 0.0177(12) 0.0007(9) -0.0002(10) 0.0009(9) O2 0.0193(12) 0.0128(12) 0.0204(13) 0.0036(10) -0.0013(10) 0.0016(10) O3 0.0218(12) 0.0148(11) 0.0160(12) 0.0006(9) 0.0030(10) 0.0032(9) O4 0.0158(11) 0.0128(11) 0.0159(11) 0.0004(9) 0.0014(9) 0.0013(8) O5 0.0180(12) 0.0201(12) 0.0222(13) 0.0017(10) 0.0042(10) 0.0056(9) N1 0.0144(12) 0.0126(13) 0.0138(13) -0.0007(10) -0.0011(10) 0.0014(10) N2 0.0159(13) 0.0156(13) 0.0129(13) -0.0001(11) -0.0012(11) 0.0003(10) N3 0.0210(14) 0.0108(12) 0.0115(13) 0.0004(10) -0.0023(11) -0.0010(10) N4 0.0169(13) 0.0155(13) 0.0098(13) 0.0018(10) 0.0002(10) 0.0009(10) C1 0.0153(15) 0.0191(16) 0.0191(17) 0.0023(14) -0.0004(13) 0.0037(12) C2 0.0177(15) 0.0128(15) 0.0189(17) -0.0020(13) 0.0015(13) 0.0064(12) C3 0.0205(16) 0.0142(15) 0.0177(17) -0.0042(13) -0.0028(13) 0.0001(12) C4 0.0215(16) 0.0197(17) 0.0133(16) -0.0046(13) 0.0003(13) 0.0001(13) C5 0.0204(16) 0.0199(16) 0.0124(15) -0.0026(13) -0.0039(13) 0.0002(13) C6 0.0215(16) 0.0133(15) 0.0135(15) 0.0013(12) -0.0031(13) 0.0012(12) C7 0.0262(17) 0.0110(14) 0.0137(15) 0.0021(12) -0.0016(13) -0.0001(13) C8 0.0279(18) 0.0134(15) 0.0173(16) -0.0027(13) -0.0046(14) -0.0034(13) C9 0.0232(17) 0.0185(17) 0.0234(18) 0.0000(14) -0.0031(14) -0.0071(13) C10 0.0161(15) 0.0239(17) 0.0217(17) 0.0008(15) -0.0026(13) -0.0041(13) C11 0.0185(15) 0.0237(17) 0.0150(16) 0.0004(14) 0.0054(13) -0.0001(13) C12 0.0198(16) 0.0225(17) 0.0156(16) 0.0025(14) 0.0046(13) -0.0006(13) C13 0.0203(15) 0.0153(15) 0.0082(14) 0.0026(12) 0.0022(12) 0.0021(12) C14 0.0229(16) 0.0138(15) 0.0141(15) -0.0022(13) 0.0006(13) 0.0036(12) C15 0.0149(14) 0.0110(14) 0.0143(15) 0.0015(12) 0.0005(12) 0.0000(11) O6 0.063(3) 0.0197(16) 0.116(4) 0.011(2) -0.057(3) -0.0158(16) O10 0.0273(14) 0.0435(18) 0.0288(16) -0.0169(14) 0.0039(12) -0.0129(13) O11 0.0346(14) 0.0193(13) 0.0184(13) -0.0027(10) 0.0002(12) 0.0062(11) O9 0.0273(14) 0.0233(14) 0.0355(17) 0.0009(13) -0.0013(13) -0.0028(11) O7 0.054(2) 0.0193(15) 0.123(4) 0.017(2) 0.048(3) 0.0052(15) O8 0.119(6) 0.033(3) 0.025(3) 0.000 0.000 0.023(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 Cu1 O4 1.993(2) . ? Cu1 N4 2.032(3) . ? Cu1 N1 2.053(3) . ? Cu1 N3 2.078(3) . ? Cu1 N2 2.220(3) . ? P1 O1 1.504(2) . ? P1 O3 1.514(3) . ? P1 O2 1.586(3) . ? P1 C15 1.822(3) . ? P1 H2P 1.94(4) . ? O2 H2P 0.694(19) . ? O4 C13 1.281(4) . ? O5 C13 1.242(4) . ? N1 C15 1.494(4) . ? N1 C2 1.504(4) . ? N1 C3 1.510(4) . ? N2 C6 1.475(4) . ? N2 C12 1.479(4) . ? N2 C5 1.482(4) . ? N3 C14 1.485(4) . ? N3 C8 1.491(4) . ? N3 C7 1.500(4) . ? N4 C10 1.495(4) . ? N4 C1 1.499(4) . ? N4 C11 1.505(4) . ? C1 C2 1.523(5) . ? C1 H1B 0.9900 . ? C1 H1C 0.9900 . ? C2 H2B 0.9900 . ? C2 H2C 0.9900 . ? C3 C4 1.517(5) . ? C3 H3B 0.9900 . ? C3 H3C 0.9900 . ? C4 C5 1.525(5) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.526(5) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.520(5) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.522(5) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.543(5) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.520(5) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? O6 H6C 0.815(10) . ? O6 H6D 0.817(10) . ? O10 H10D 0.823(10) . ? O10 H10C 0.820(10) . ? O11 H11D 0.818(7) . ? O11 H11C 0.817(7) . ? O9 H9D 1.03(6) . ? O9 H9C 0.72(6) . ? O7 H7D 0.815(10) . ? O7 H7C 0.816(10) . ? O8 H8C 0.819(10) . ? 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 O4 Cu1 N4 178.47(11) . . ? O4 Cu1 N1 92.37(10) . . ? N4 Cu1 N1 86.31(11) . . ? O4 Cu1 N3 83.46(10) . . ? N4 Cu1 N3 97.89(11) . . ? N1 Cu1 N3 175.02(11) . . ? O4 Cu1 N2 93.10(10) . . ? N4 Cu1 N2 86.34(11) . . ? N1 Cu1 N2 99.06(11) . . ? N3 Cu1 N2 83.93(11) . . ? O1 P1 O3 118.05(14) . . ? O1 P1 O2 108.06(14) . . ? O3 P1 O2 109.84(14) . . ? O1 P1 C15 108.27(14) . . ? O3 P1 C15 104.91(15) . . ? O2 P1 C15 107.21(14) . . ? O1 P1 H2P 127.7(11) . . ? O3 P1 H2P 95.4(13) . . ? O2 P1 H2P 19.7(10) . . ? C15 P1 H2P 99.3(15) . . ? P1 O2 H2P 110(4) . . ? C13 O4 Cu1 114.1(2) . . ? C15 N1 C2 111.2(3) . . ? C15 N1 C3 107.4(2) . . ? C2 N1 C3 110.0(3) . . ? C15 N1 Cu1 107.49(19) . . ? C2 N1 Cu1 108.70(19) . . ? C3 N1 Cu1 112.1(2) . . ? C6 N2 C12 111.5(3) . . ? C6 N2 C5 110.6(3) . . ? C12 N2 C5 113.4(3) . . ? C6 N2 Cu1 102.49(19) . . ? C12 N2 Cu1 105.5(2) . . ? C5 N2 Cu1 112.8(2) . . ? C14 N3 C8 110.3(3) . . ? C14 N3 C7 109.6(3) . . ? C8 N3 C7 109.7(3) . . ? C14 N3 Cu1 102.66(19) . . ? C8 N3 Cu1 115.1(2) . . ? C7 N3 Cu1 109.2(2) . . ? C10 N4 C1 106.8(3) . . ? C10 N4 C11 112.7(3) . . ? C1 N4 C11 109.3(3) . . ? C10 N4 Cu1 113.3(2) . . ? C1 N4 Cu1 104.77(19) . . ? C11 N4 Cu1 109.5(2) . . ? N4 C1 C2 110.5(3) . . ? N4 C1 H1B 109.6 . . ? C2 C1 H1B 109.6 . . ? N4 C1 H1C 109.6 . . ? C2 C1 H1C 109.6 . . ? H1B C1 H1C 108.1 . . ? N1 C2 C1 111.0(3) . . ? N1 C2 H2B 109.4 . . ? C1 C2 H2B 109.4 . . ? N1 C2 H2C 109.4 . . ? C1 C2 H2C 109.4 . . ? H2B C2 H2C 108.0 . . ? N1 C3 C4 116.3(3) . . ? N1 C3 H3B 108.2 . . ? C4 C3 H3B 108.2 . . ? N1 C3 H3C 108.2 . . ? C4 C3 H3C 108.2 . . ? H3B C3 H3C 107.4 . . ? C3 C4 C5 116.0(3) . . ? C3 C4 H4A 108.3 . . ? C5 C4 H4A 108.3 . . ? C3 C4 H4B 108.3 . . ? C5 C4 H4B 108.3 . . ? H4A C4 H4B 107.4 . . ? N2 C5 C4 115.2(3) . . ? N2 C5 H5A 108.5 . . ? C4 C5 H5A 108.5 . . ? N2 C5 H5B 108.5 . . ? C4 C5 H5B 108.5 . . ? H5A C5 H5B 107.5 . . ? N2 C6 C7 110.8(3) . . ? N2 C6 H6A 109.5 . . ? C7 C6 H6A 109.5 . . ? N2 C6 H6B 109.5 . . ? C7 C6 H6B 109.5 . . ? H6A C6 H6B 108.1 . . ? N3 C7 C6 113.9(3) . . ? N3 C7 H7A 108.8 . . ? C6 C7 H7A 108.8 . . ? N3 C7 H7B 108.8 . . ? C6 C7 H7B 108.8 . . ? H7A C7 H7B 107.7 . . ? N3 C8 C9 113.9(3) . . ? N3 C8 H8A 108.8 . . ? C9 C8 H8A 108.8 . . ? N3 C8 H8B 108.8 . . ? C9 C8 H8B 108.8 . . ? H8A C8 H8B 107.7 . . ? C8 C9 C10 113.6(3) . . ? C8 C9 H9A 108.8 . . ? C10 C9 H9A 108.8 . . ? C8 C9 H9B 108.8 . . ? C10 C9 H9B 108.8 . . ? H9A C9 H9B 107.7 . . ? N4 C10 C9 116.2(3) . . ? N4 C10 H10A 108.2 . . ? C9 C10 H10A 108.2 . . ? N4 C10 H10B 108.2 . . ? C9 C10 H10B 108.2 . . ? H10A C10 H10B 107.4 . . ? N4 C11 C12 114.9(3) . . ? N4 C11 H11A 108.5 . . ? C12 C11 H11A 108.5 . . ? N4 C11 H11B 108.5 . . ? C12 C11 H11B 108.5 . . ? H11A C11 H11B 107.5 . . ? N2 C12 C11 114.3(3) . . ? N2 C12 H12A 108.7 . . ? C11 C12 H12A 108.7 . . ? N2 C12 H12B 108.7 . . ? C11 C12 H12B 108.7 . . ? H12A C12 H12B 107.6 . . ? O5 C13 O4 123.8(3) . . ? O5 C13 C14 120.8(3) . . ? O4 C13 C14 115.4(3) . . ? N3 C14 C13 109.8(3) . . ? N3 C14 H14A 109.7 . . ? C13 C14 H14A 109.7 . . ? N3 C14 H14B 109.7 . . ? C13 C14 H14B 109.7 . . ? H14A C14 H14B 108.2 . . ? N1 C15 P1 115.9(2) . . ? N1 C15 H15A 108.3 . . ? P1 C15 H15A 108.3 . . ? N1 C15 H15B 108.3 . . ? P1 C15 H15B 108.3 . . ? H15A C15 H15B 107.4 . . ? H6C O6 H6D 106(3) . . ? H10D O10 H10C 104(2) . . ? H11D O11 H11C 106.1(18) . . ? H9D O9 H9C 119(5) . . ? H7D O7 H7C 107(3) . . ? 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 O9 H9D O7 1.03(6) 1.80(6) 2.800(5) 162(4) . O9 H9C O6 0.72(6) 2.06(6) 2.763(5) 166(6) . O6 H6C O9 0.815(10) 2.07(5) 2.763(5) 143(8) . O10 H10C O4 0.820(10) 2.112(13) 2.928(4) 173(5) . O11 H11D O1 0.818(7) 1.917(15) 2.707(4) 162(5) . O11 H11C O5 0.817(7) 2.30(3) 2.970(4) 140(4) 8_656 O2 H2P O3 0.694(19) 1.90(2) 2.599(3) 178(6) 5_666 O7 H7D O11 0.815(10) 1.92(3) 2.715(4) 164(8) 7_575 O8 H8C O6 0.819(10) 2.55(2) 3.337(7) 163(7) . _diffrn_measured_fraction_theta_max 0.958 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.585 _refine_diff_density_min -0.520 _refine_diff_density_rms 0.093