Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Mitch Malachowski' _publ_contact_author_address ; Department of Chemistry University of San Diego Alcala Park San Diego CA 92110 ; _publ_contact_author_email MALACHOW@SANDIEGO.EDU _publ_section_title ; Synthesis, Structure, Redox Properties and Azide Binding for a Series of Biphenyl-based Cu(II) Complexes ; loop_ _publ_author_name 'Mitch Malachowski' 'Wilson Chao' 'Jacky Chen' 'Lawrence D. Margerum' 'Arnold Rheingold' 'Robert Russo' ; Z.Thawley ; 'Angie Thayer' 'Ryan White' 'Lev N. Zakharov' data_mrm33 _database_code_depnum_ccdc_archive 'CCDC 634478' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H27.60 Cl2 Cu N5 O4.30' _chemical_formula_weight 637.39 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' Cl Cl 0.1484 0.1585 '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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.3313(10) _cell_length_b 12.8655(14) _cell_length_c 13.1271(14) _cell_angle_alpha 110.350(2) _cell_angle_beta 95.181(2) _cell_angle_gamma 102.478(2) _cell_volume 1418.9(3) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9680 _cell_measurement_theta_min 0.00 _cell_measurement_theta_max 0.00 _exptl_crystal_description Block _exptl_crystal_colour Green _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.492 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 1.003 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.773 _exptl_absorpt_correction_T_max 0.853 _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_reflns_number 12149 _diffrn_reflns_av_R_equivalents 0.0258 _diffrn_reflns_av_sigmaI/netI 0.0391 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.68 _diffrn_reflns_theta_max 27.54 _reflns_number_total 6271 _reflns_number_gt 5667 _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, 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^)+(0.0460P)^2^+1.0327P] 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 6271 _refine_ls_number_parameters 473 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0393 _refine_ls_R_factor_gt 0.0356 _refine_ls_wR_factor_ref 0.0926 _refine_ls_wR_factor_gt 0.0906 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.002 _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 Cu1 Cu 0.10864(3) 0.200038(19) 0.305001(19) 0.01577(8) Uani 1 1 d . . . Cl1 Cl 0.14783(6) 0.14749(4) 0.12864(4) 0.02238(12) Uani 1 1 d . . . Cl2 Cl 0.25745(5) 0.13164(4) 0.41762(4) 0.02045(11) Uani 1 1 d . . . O1 O -0.13803(18) -0.07999(13) 0.39054(13) 0.0228(3) Uani 1 1 d . . . O2 O -0.62857(18) -0.43806(14) -0.00341(14) 0.0294(4) Uani 1 1 d . . . O3 O -0.47393(19) -0.37067(14) -0.09221(13) 0.0326(4) Uani 1 1 d . . . N1 N 0.2489(2) 0.35769(14) 0.35547(14) 0.0192(4) Uani 1 1 d . . . N2 N 0.00530(19) 0.29030(15) 0.43444(15) 0.0226(4) Uani 1 1 d . . . N3 N -0.07036(19) 0.06445(13) 0.26830(15) 0.0165(3) Uani 1 1 d . . . N4 N -0.5120(2) -0.37376(15) -0.00586(15) 0.0225(4) Uani 1 1 d . . . C1 C 0.3603(2) 0.39165(18) 0.30805(18) 0.0219(4) Uani 1 1 d . . . C2 C 0.4484(3) 0.50445(19) 0.3488(2) 0.0259(5) Uani 1 1 d . . . C3 C 0.4195(3) 0.58438(18) 0.4401(2) 0.0280(5) Uani 1 1 d . . . C4 C 0.3042(3) 0.54923(18) 0.49057(19) 0.0262(5) Uani 1 1 d . . . C5 C 0.2219(3) 0.43505(17) 0.44646(18) 0.0235(4) Uani 1 1 d . . . C6 C 0.1041(4) 0.3895(2) 0.4985(2) 0.0411(7) Uani 1 1 d . . . C7 C -0.1045(2) 0.24084(17) 0.48640(18) 0.0202(4) Uani 1 1 d . . . C8 C -0.0740(3) 0.26083(19) 0.59838(19) 0.0252(5) Uani 1 1 d . . . C9 C -0.1811(3) 0.2147(2) 0.6484(2) 0.0290(5) Uani 1 1 d . . . C10 C -0.3209(3) 0.1490(2) 0.5871(2) 0.0303(5) Uani 1 1 d . . . C11 C -0.3515(3) 0.12845(18) 0.4759(2) 0.0260(5) Uani 1 1 d . . . C12 C -0.2446(2) 0.17157(16) 0.42260(18) 0.0209(4) Uani 1 1 d . . . C13 C -0.2827(2) 0.14730(16) 0.30254(18) 0.0205(4) Uani 1 1 d . . . C14 C -0.4101(2) 0.17167(19) 0.2613(2) 0.0268(5) Uani 1 1 d . . . C15 C -0.4476(3) 0.1490(2) 0.1503(2) 0.0306(5) Uani 1 1 d . . . C16 C -0.3593(3) 0.10140(19) 0.0778(2) 0.0277(5) Uani 1 1 d . . . C17 C -0.2344(2) 0.07308(18) 0.11591(19) 0.0228(4) Uani 1 1 d . . . C18 C -0.1985(2) 0.09472(16) 0.22750(17) 0.0183(4) Uani 1 1 d . . . C19 C -0.0578(2) -0.05316(16) 0.20249(18) 0.0181(4) Uani 1 1 d . . . C20 C -0.1942(2) -0.14419(16) 0.19718(17) 0.0183(4) Uani 1 1 d . . . C21 C -0.2312(2) -0.15370(17) 0.29603(17) 0.0199(4) Uani 1 1 d . . . C22 C -0.3588(3) -0.23422(19) 0.29450(19) 0.0244(5) Uani 1 1 d . . . C23 C -0.4516(3) -0.30625(19) 0.19534(19) 0.0239(4) Uani 1 1 d . . . C24 C -0.4140(2) -0.29684(17) 0.09872(17) 0.0207(4) Uani 1 1 d . . . C25 C -0.2873(2) -0.21698(17) 0.09826(18) 0.0191(4) Uani 1 1 d . . . O4 O -0.9386(3) 0.5704(2) 0.71621(16) 0.0576(6) Uani 1 1 d . . . N5 N -0.9684(2) 0.61831(17) 0.89519(17) 0.0303(4) Uani 1 1 d . . . C26 C -0.8910(3) 0.6201(2) 0.8158(2) 0.0375(6) Uani 1 1 d . . . C27 C -1.1235(3) 0.5558(3) 0.8687(3) 0.0464(7) Uani 1 1 d . . . C28 C -0.9091(4) 0.6951(3) 1.0087(2) 0.0448(7) Uani 1 1 d . . . O5 O -0.7005(10) 0.9404(8) 0.1938(8) 0.070(2) Uiso 0.30 1 d P . . H1 H 0.375(3) 0.336(2) 0.247(2) 0.019(6) Uiso 1 1 d . . . H2 H 0.517(3) 0.521(2) 0.313(2) 0.027(7) Uiso 1 1 d . . . H3 H 0.471(3) 0.653(3) 0.469(2) 0.036(8) Uiso 1 1 d . . . H4 H 0.280(3) 0.600(2) 0.551(2) 0.025(6) Uiso 1 1 d . . . H6 H 0.079(3) 0.437(2) 0.552(2) 0.026(7) Uiso 1 1 d . . . H8 H 0.018(3) 0.302(2) 0.639(2) 0.031(7) Uiso 1 1 d . . . H9 H -0.155(3) 0.231(2) 0.724(2) 0.034(7) Uiso 1 1 d . . . H10 H -0.395(3) 0.120(2) 0.619(2) 0.036(7) Uiso 1 1 d . . . H11 H -0.447(3) 0.083(2) 0.436(2) 0.019(6) Uiso 1 1 d . . . H14 H -0.473(3) 0.202(2) 0.309(2) 0.038(8) Uiso 1 1 d . . . H15 H -0.534(3) 0.163(2) 0.124(2) 0.031(7) Uiso 1 1 d . . . H16 H -0.378(3) 0.089(2) 0.001(2) 0.026(7) Uiso 1 1 d . . . H17 H -0.175(3) 0.040(2) 0.068(2) 0.018(6) Uiso 1 1 d . . . H19A H 0.039(3) -0.059(2) 0.2403(19) 0.018(6) Uiso 1 1 d . . . H19B H -0.042(3) -0.0570(19) 0.132(2) 0.015(5) Uiso 1 1 d . . . H22 H -0.385(3) -0.238(3) 0.360(3) 0.044(8) Uiso 1 1 d . . . H23 H -0.534(3) -0.357(2) 0.192(2) 0.022(6) Uiso 1 1 d . . . H25 H -0.268(3) -0.214(2) 0.033(2) 0.020(6) Uiso 1 1 d . . . H26 H -0.781(3) 0.661(3) 0.846(2) 0.043(8) Uiso 1 1 d . . . H27A H -1.189(4) 0.609(3) 0.880(3) 0.062(10) Uiso 1 1 d . . . H27B H -1.146(4) 0.516(3) 0.924(3) 0.078(12) Uiso 1 1 d . . . H27C H -1.145(4) 0.501(3) 0.798(3) 0.057(10) Uiso 1 1 d . . . H28A H -0.923(4) 0.653(3) 1.051(3) 0.063(11) Uiso 1 1 d . . . H28B H -0.960(3) 0.750(3) 1.027(2) 0.040(8) Uiso 1 1 d . . . H28C H -0.789(4) 0.728(3) 1.017(3) 0.051(9) Uiso 1 1 d . . . H3N H -0.073(3) 0.066(2) 0.334(2) 0.016(6) Uiso 1 1 d . . . H1O H -0.169(3) -0.092(3) 0.436(2) 0.033(8) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.01880(13) 0.01129(12) 0.01434(13) 0.00319(9) 0.00358(9) 0.00071(9) Cl1 0.0255(3) 0.0194(2) 0.0162(2) 0.00308(19) 0.00679(19) -0.00163(19) Cl2 0.0198(2) 0.0222(2) 0.0200(2) 0.0106(2) 0.00273(18) 0.00299(18) O1 0.0270(8) 0.0212(7) 0.0171(8) 0.0073(6) 0.0038(6) 0.0000(6) O2 0.0258(8) 0.0262(8) 0.0296(9) 0.0098(7) 0.0038(7) -0.0048(6) O3 0.0389(10) 0.0309(9) 0.0199(8) 0.0093(7) 0.0037(7) -0.0056(7) N1 0.0244(9) 0.0135(7) 0.0168(8) 0.0048(7) 0.0034(7) 0.0009(7) N2 0.0174(8) 0.0214(8) 0.0194(9) 0.0000(7) 0.0060(7) -0.0020(7) N3 0.0190(8) 0.0117(7) 0.0160(9) 0.0026(7) 0.0036(7) 0.0025(6) N4 0.0240(9) 0.0181(8) 0.0237(9) 0.0084(7) 0.0034(7) 0.0016(7) C1 0.0252(11) 0.0184(10) 0.0201(11) 0.0078(9) 0.0023(8) 0.0019(8) C2 0.0253(11) 0.0218(10) 0.0290(12) 0.0141(10) -0.0001(9) -0.0027(9) C3 0.0339(12) 0.0135(10) 0.0289(12) 0.0080(9) -0.0070(10) -0.0041(9) C4 0.0377(13) 0.0138(9) 0.0209(11) 0.0030(9) -0.0011(9) 0.0027(9) C5 0.0343(12) 0.0153(9) 0.0185(10) 0.0055(8) 0.0043(9) 0.0031(8) C6 0.070(2) 0.0137(10) 0.0336(14) 0.0009(10) 0.0348(14) 0.0028(11) C7 0.0197(10) 0.0155(9) 0.0231(11) 0.0036(8) 0.0081(8) 0.0043(8) C8 0.0268(11) 0.0201(10) 0.0253(11) 0.0051(9) 0.0079(9) 0.0042(9) C9 0.0385(13) 0.0251(11) 0.0268(12) 0.0108(10) 0.0141(10) 0.0102(10) C10 0.0310(12) 0.0226(11) 0.0430(14) 0.0153(10) 0.0210(11) 0.0075(9) C11 0.0213(11) 0.0164(9) 0.0377(13) 0.0066(9) 0.0106(10) 0.0034(8) C12 0.0195(10) 0.0127(9) 0.0267(11) 0.0021(8) 0.0073(8) 0.0041(8) C13 0.0166(9) 0.0127(9) 0.0265(11) 0.0027(8) 0.0034(8) 0.0005(7) C14 0.0185(10) 0.0189(10) 0.0349(13) 0.0016(9) 0.0025(9) 0.0041(8) C15 0.0207(11) 0.0241(11) 0.0408(14) 0.0075(10) -0.0037(10) 0.0051(9) C16 0.0271(11) 0.0224(10) 0.0262(12) 0.0057(9) -0.0045(9) 0.0010(9) C17 0.0233(10) 0.0155(9) 0.0233(11) 0.0033(8) 0.0012(9) 0.0008(8) C18 0.0172(9) 0.0103(8) 0.0218(10) 0.0020(8) 0.0012(8) 0.0003(7) C19 0.0211(10) 0.0125(9) 0.0191(10) 0.0032(8) 0.0073(8) 0.0043(7) C20 0.0209(10) 0.0128(8) 0.0207(10) 0.0050(8) 0.0075(8) 0.0045(7) C21 0.0236(10) 0.0163(9) 0.0190(10) 0.0060(8) 0.0047(8) 0.0047(8) C22 0.0294(11) 0.0225(10) 0.0198(11) 0.0094(9) 0.0066(9) 0.0008(9) C23 0.0237(11) 0.0216(10) 0.0247(11) 0.0106(9) 0.0054(9) -0.0011(9) C24 0.0251(10) 0.0155(9) 0.0190(10) 0.0051(8) 0.0039(8) 0.0027(8) C25 0.0253(10) 0.0143(9) 0.0188(10) 0.0066(8) 0.0080(8) 0.0053(8) O4 0.0590(14) 0.0645(14) 0.0256(10) -0.0084(10) 0.0055(9) 0.0125(11) N5 0.0340(11) 0.0275(10) 0.0297(11) 0.0090(9) 0.0061(9) 0.0117(8) C26 0.0400(15) 0.0311(13) 0.0303(14) -0.0003(11) 0.0089(11) 0.0057(11) C27 0.0354(15) 0.0465(17) 0.061(2) 0.0247(17) 0.0108(14) 0.0106(13) C28 0.0584(19) 0.0534(18) 0.0255(14) 0.0102(13) 0.0090(13) 0.0277(16) _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 N1 2.0069(17) . ? Cu1 N3 2.0189(16) . ? Cu1 N2 2.1384(18) . ? Cu1 Cl1 2.2631(6) . ? Cu1 Cl2 2.4393(6) . ? O1 C21 1.351(3) . ? O1 H1O 0.73(3) . ? O2 N4 1.227(2) . ? O3 N4 1.229(2) . ? N1 C1 1.330(3) . ? N1 C5 1.348(3) . ? N2 C6 1.338(3) . ? N2 C7 1.437(3) . ? N3 C18 1.448(3) . ? N3 C19 1.495(2) . ? N3 H3N 0.86(2) . ? N4 C24 1.462(3) . ? C1 C2 1.390(3) . ? C1 H1 0.92(3) . ? C2 C3 1.374(4) . ? C2 H2 0.86(3) . ? C3 C4 1.389(4) . ? C3 H3 0.84(3) . ? C4 C5 1.387(3) . ? C4 H4 0.91(3) . ? C5 C6 1.468(3) . ? C6 H6 0.85(3) . ? C7 C8 1.392(3) . ? C7 C12 1.409(3) . ? C8 C9 1.384(3) . ? C8 H8 0.91(3) . ? C9 C10 1.387(4) . ? C9 H9 0.94(3) . ? C10 C11 1.381(4) . ? C10 H10 0.92(3) . ? C11 C12 1.396(3) . ? C11 H11 0.94(2) . ? C12 C13 1.489(3) . ? C13 C18 1.397(3) . ? C13 C14 1.403(3) . ? C14 C15 1.378(4) . ? C14 H14 0.94(3) . ? C15 C16 1.383(4) . ? C15 H15 0.92(3) . ? C16 C17 1.395(3) . ? C16 H16 0.96(3) . ? C17 C18 1.387(3) . ? C17 H17 0.93(2) . ? C19 C20 1.510(3) . ? C19 H19A 1.02(2) . ? C19 H19B 0.94(2) . ? C20 C25 1.384(3) . ? C20 C21 1.411(3) . ? C21 C22 1.393(3) . ? C22 C23 1.383(3) . ? C22 H22 0.93(3) . ? C23 C24 1.384(3) . ? C23 H23 0.88(3) . ? C24 C25 1.391(3) . ? C25 H25 0.91(3) . ? O4 C26 1.228(3) . ? N5 C26 1.324(3) . ? N5 C27 1.439(4) . ? N5 C28 1.447(4) . ? C26 H26 1.02(3) . ? C27 H27A 1.00(4) . ? C27 H27B 1.04(4) . ? C27 H27C 0.92(4) . ? C28 H28A 0.90(4) . ? C28 H28B 0.91(3) . ? C28 H28C 1.09(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cu1 N3 165.33(7) . . ? N1 Cu1 N2 80.56(7) . . ? N3 Cu1 N2 86.53(7) . . ? N1 Cu1 Cl1 94.48(5) . . ? N3 Cu1 Cl1 93.43(5) . . ? N2 Cu1 Cl1 150.87(6) . . ? N1 Cu1 Cl2 95.22(5) . . ? N3 Cu1 Cl2 93.01(5) . . ? N2 Cu1 Cl2 95.96(6) . . ? Cl1 Cu1 Cl2 113.11(2) . . ? C21 O1 H1O 107(2) . . ? C1 N1 C5 118.77(18) . . ? C1 N1 Cu1 126.96(15) . . ? C5 N1 Cu1 114.26(14) . . ? C6 N2 C7 116.86(18) . . ? C6 N2 Cu1 108.23(15) . . ? C7 N2 Cu1 126.99(13) . . ? C18 N3 C19 115.13(16) . . ? C18 N3 Cu1 107.37(12) . . ? C19 N3 Cu1 118.83(13) . . ? C18 N3 H3N 111.0(16) . . ? C19 N3 H3N 105.0(16) . . ? Cu1 N3 H3N 98.1(16) . . ? O2 N4 O3 123.03(18) . . ? O2 N4 C24 118.55(18) . . ? O3 N4 C24 118.42(17) . . ? N1 C1 C2 122.0(2) . . ? N1 C1 H1 115.7(15) . . ? C2 C1 H1 122.3(15) . . ? C3 C2 C1 119.5(2) . . ? C3 C2 H2 123.4(18) . . ? C1 C2 H2 117.1(18) . . ? C2 C3 C4 118.7(2) . . ? C2 C3 H3 123(2) . . ? C4 C3 H3 118(2) . . ? C5 C4 C3 118.8(2) . . ? C5 C4 H4 119.6(16) . . ? C3 C4 H4 121.6(16) . . ? N1 C5 C4 122.2(2) . . ? N1 C5 C6 115.63(18) . . ? C4 C5 C6 122.2(2) . . ? N2 C6 C5 116.3(2) . . ? N2 C6 H6 119.9(18) . . ? C5 C6 H6 117.8(18) . . ? C8 C7 C12 120.0(2) . . ? C8 C7 N2 120.86(19) . . ? C12 C7 N2 119.18(19) . . ? C9 C8 C7 120.6(2) . . ? C9 C8 H8 118.9(18) . . ? C7 C8 H8 120.4(18) . . ? C8 C9 C10 119.9(2) . . ? C8 C9 H9 117.4(17) . . ? C10 C9 H9 122.6(17) . . ? C11 C10 C9 119.7(2) . . ? C11 C10 H10 118.7(18) . . ? C9 C10 H10 121.5(18) . . ? C10 C11 C12 121.7(2) . . ? C10 C11 H11 118.4(15) . . ? C12 C11 H11 120.0(15) . . ? C11 C12 C7 118.1(2) . . ? C11 C12 C13 119.77(19) . . ? C7 C12 C13 122.08(19) . . ? C18 C13 C14 118.3(2) . . ? C18 C13 C12 121.55(19) . . ? C14 C13 C12 120.1(2) . . ? C15 C14 C13 120.9(2) . . ? C15 C14 H14 118.9(18) . . ? C13 C14 H14 120.2(18) . . ? C14 C15 C16 120.1(2) . . ? C14 C15 H15 119.8(17) . . ? C16 C15 H15 120.1(17) . . ? C15 C16 C17 120.3(2) . . ? C15 C16 H16 122.4(15) . . ? C17 C16 H16 117.3(15) . . ? C18 C17 C16 119.3(2) . . ? C18 C17 H17 119.7(15) . . ? C16 C17 H17 121.1(15) . . ? C17 C18 C13 121.1(2) . . ? C17 C18 N3 120.02(19) . . ? C13 C18 N3 118.86(18) . . ? N3 C19 C20 111.02(16) . . ? N3 C19 H19A 104.8(13) . . ? C20 C19 H19A 113.9(13) . . ? N3 C19 H19B 109.3(14) . . ? C20 C19 H19B 111.9(14) . . ? H19A C19 H19B 105.5(19) . . ? C25 C20 C21 118.62(18) . . ? C25 C20 C19 122.04(19) . . ? C21 C20 C19 119.32(18) . . ? O1 C21 C22 122.7(2) . . ? O1 C21 C20 116.48(18) . . ? C22 C21 C20 120.86(19) . . ? C23 C22 C21 120.2(2) . . ? C23 C22 H22 119.1(19) . . ? C21 C22 H22 120.7(19) . . ? C22 C23 C24 118.6(2) . . ? C22 C23 H23 121.7(16) . . ? C24 C23 H23 119.7(16) . . ? C23 C24 C25 122.2(2) . . ? C23 C24 N4 118.32(18) . . ? C25 C24 N4 119.44(19) . . ? C20 C25 C24 119.5(2) . . ? C20 C25 H25 121.7(15) . . ? C24 C25 H25 118.7(15) . . ? C26 N5 C27 120.6(2) . . ? C26 N5 C28 120.9(2) . . ? C27 N5 C28 117.5(3) . . ? O4 C26 N5 125.8(3) . . ? O4 C26 H26 121.6(17) . . ? N5 C26 H26 112.2(17) . . ? N5 C27 H27A 111(2) . . ? N5 C27 H27B 109(2) . . ? H27A C27 H27B 104(3) . . ? N5 C27 H27C 110(2) . . ? H27A C27 H27C 113(3) . . ? H27B C27 H27C 109(3) . . ? N5 C28 H28A 108(2) . . ? N5 C28 H28B 108.4(19) . . ? H28A C28 H28B 110(3) . . ? N5 C28 H28C 108.2(17) . . ? H28A C28 H28C 107(3) . . ? H28B C28 H28C 115(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 N3 H3N O1 0.86(2) 2.23(2) 2.860(2) 130(2) . O1 H1O Cl2 0.73(3) 2.33(3) 3.0620(18) 178(3) 2_556 _diffrn_measured_fraction_theta_max 0.959 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.588 _refine_diff_density_min -0.597 _refine_diff_density_rms 0.069